PM16 Supplementary BCPC PDF

A World Compendium
The Pesticide Manual

Sixteenth Edition
Supplementary Entries Extended
Editor: C. MacBean
Promoting the science and practice of sustainable crop production

2012 BCPC (British Crop Production Council)
All rights reserved. No part of this publication may be reproduced, stored in a retrieval system,
or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or
otherwise, without the prior permission of the copyright owner.
British Library Cataloguing in Publication Data. A catalogue record of this book is available from
the British Library.
ISBN 978 1 901396 86 7
First published 1968 Seventh edition 1983 Thirteenth edition 2003

Second edition 1971 Eighth edition 1987 Fourteenth edition 2006
Third edition 1972 Ninth edition 1991 Fifteenth edition 2009
Fourth edition 1974 Tenth edition* 1994
Fifth edition 1977 Eleventh edition 1997
Sixth edition 1979 Twelfth edition 2000
* The tenth edition incorporated The Agrochemicals Handbook, previously published by
The Royal Society of Chemistry.
Published by: BCPC, 7 Omni Business Centre, Omega Park, Alton, Hampshire, GU34 2QD, UK
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Disclaimer: Every effort has been made to ensure that all information in this edition of
The Pesticide Manual is correct at the time of going to press. However, the editor and the
publisher do not accept liability for any error or omission in the content, or for any loss,
damage or any other accident arising from the use of the products listed therein. Before
handling, storing or using any approved crop protection product, it is essential to follow the
instructions on the label.
Supplementary Entries
These entries include (i) superseded materials, believed to be no longer manufactured,
or marketed, for crop protection use; (ii) some materials that are in the public domain
and believed to be in late stages of development; and (iii) materials that reached late
development but were ultimately not marketed.
These entries are short descriptions. For chemical materials, they may include the
following information:
Sequential entry number.
A header name, with an indication of the type of name (such as common name, chemical
name, etc.).
Chemical Abstracts Service Registry Number (CAS RN).
Approved common name (if different from the name in the header, or if other common
names have been approved by national bodies).
Molecular formula (M.f.).
Other names.
Code numbers (development codes).
The main former product or products.
For an explanation of this information see the Guide to Using the Main Entries, p. viii of
The Pesticide Manual Sixteenth Edition.
It is difficult, in some cases, to be sure whether or not all commercial activity in a
substance has ceased; some of these superseded materials are known to be still in use
for non-agricultural purposes. The Editor will be grateful for details of any materials in this
section that are still in commercial, agricultural use; he can be contacted via the publishers,
or at pm@bcpc.org.
iii
AC94,377
Plant growth regulator
Cl O
N
NH2
O O
NOMENCLATURE:
IUPACname 1-(4-chloro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)cyclohexane-1-
carboxamide; 1-phthalimidocyclohexane-1-carboxamide
Chemical Abstracts name 1-(4-chloro-1,3-dihydro-1,3-dioxo-[2H]-isoindol-2-yl)-
cyclohexanecarboxamide CASRN[51971676] DevelopmentcodesAC94,377;
CL94,377 (both Cyanamid)
SmilescodeNC(=O)C1(CCCCC1)N2C(=O)c3cccc(Cl)c3C2=O
PHYSICAL CHEMISTRY: Mol. wt. 306.7 M.f. C15H15ClN2O3 Form White
crystalline solid. M.p.193195C Solubility In water 30 ppm (25C). In acetone <2%,
N-methylpyrrolidone 35%, dichloromethane <2%, DMSO >20% (all 20C).
COMMERCIALISATION:
History Evaluated by American Cyanamid Co.
APPLICATIONS:
Biochemistry Not known. Activity mimics that of gibberellic acid in various
phytohormone bioassays (J. C. Suttle & J. F. Hultstrand, Plant Physiology, 80 (5), 115 (1986)).
Uses Growth promoter, increasing the stem number, stem length and commercial
acceptability of cut stems in hybrid tea roses. Beneficial effects have been reported in other
crops. Formulation types SC.
PRODUCTS:
Discontinued products Surestem* (BASF).
MAMMALIAN TOXICOLOGY:
Oral Acute oral LD50 for male and female rats >5000 mg/kg. Skin and eye Acute
percutaneous LD50 for male and female rabbits >2000 mg/kg. Mildly irritating to eyes;
non-irritating to skin (male rabbits). Other Non-mutagenic in the Ames test, microbial
mutagenicity assay, and host-mediated assay.
Details PM12, Entry 3.
AC94,377 1
The Pesticide Manual Sixteenth Edition BCPC 2012
ACD 10614; ACD 10435

Herbicide
NOMENCLATURE:
IUPACname 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)hept-3-ene-2,6-diol
(i) and tautomer 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-bis(trifluoromethyl)heptane-2,6-
diol (ii); forming monosodium 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)
hept-3-ene-2,6-diolate and monosodium 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-
bis(trifluoromethyl)heptane-2,6-diolate
Chemical Abstracts name 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)-3-
heptene-2,6-diol (i) and 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-bis(trifluoromethyl)-2,6-
heptanediol (ii) CASRN[756912] (i); [16202918] (ii); [19493948] monosodium
salts DevelopmentcodesACD 10 614 (i +ii); ACD 10 435 (monosodium salts)
PHYSICAL CHEMISTRY: Mol. wt. 388.2 M.f. C10H8F12O2 Form Monosodium
salts form a colourless solid. M.p.143145C; monosodium salts >300C Solubility
Practically insoluble in water, benzene, dichloromethane, xylene; soluble in alkali, acetone,
diethyl ether, DMF, DMSO, dioxane, bis(2-methoxyethyl) ether. Sodium salt soluble in water,
acetone, diethyl ether, dioxane, ethanol; insoluble in benzene, hexane.
COMMERCIALISATION:
History Herbicide evaluated by Allied Chemical Corp., Agrochemical Division (later
Hopkins Agricultural Chemical Co.).
APPLICATIONS:
ModeofactionSelective herbicide. Uses Both the diol and its monosodium salt pre-em.
at 2.36.8 kg/ha controlled weeds selectively in cereals, maize, sorghum and soya beans;
and post-em. at 2.3 kg/ha in maize, sorghum, soya beans and wheat. Formulation types
EC (diol); GR (diol); SP (hydrated sodium salt); WP (diol).
Oral Diol: Acute oral LD50 for fasted albino rats 17.8 mg/kg. Monosodium salt: 20.2 mg/kg.
Skin and eye Acute percutaneous LD50 for albino rabbits 141 mg/kg.
Details PM4, p. 296.
acetic acid
Herbicide
See also The Manual of Biocontrol Agents 4th edn entry: 2:151
NOMENCLATURE:
CASRN[64197]
PRODUCTS:
Other products Natures Glory Weed & Grass Killer (Ecoval).
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:
EU Rev. Rep. SANCO/2602/08 (2008) EU Status (1107/2009) 2008/127/EC
2 acetic acid
acetoprole
Acaricide, insecticide, nematicide
NOMENCLATURE:
Common name (m) ac(toprole) (F-ISO); acetoprole (BSI, E-ISO)
IUPACname ()-1-[5-amino-1-(2,6-dichloro-,,-trifluoro-p-tolyl)-4-(methylsulfinyl)
pyrazol-3-yl]ethanone
Chemical Abstracts name 1-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)
phenyl]-4-(methylsulfinyl)-1H-pyrazol-3-yl]ethanone CASRN[209861585]
DevelopmentcodesRPA 115782
PHYSICAL CHEMISTRY: Mol. wt. 400.2 M.f. C13H10Cl2F3N3O2S
COMMERCIALISATION:
Manufacturers Rhne-Poulenc
acrylonitrile
Insecticide
NOMENCLATURE:
Common name acrylonitrile (BSI, E-ISO, F-ISO, ESA, accepted in lieu of a common name)
IUPACname acrylonitrile
Chemical Abstracts name 2-propenenitrile Other names vinyl cyanide
CASRN[107131] ECno2034665 SmilescodeC=CC#N
PHYSICAL CHEMISTRY: Mol. wt. 53.06 M.f. C3H3N M.p.82C B.p. 77C V.p.
1.37 107 mPa (25C) S.g./density 0.801 (425C); gaseous, 1.83 (air = 1) Solubility
In water ca. 8% (room temperature). Unlimited miscibility with common organic solvents.
Stability Readily polymerised, sometimes explosively. Addition of stabilizers is necessary.
F.p. 0C. Mixtures with air having 317% vol./vol. acrylonitrile are flammable.
COMMERCIALISATION:
History Developed as a fumigant insecticide (The Chemistry of Acrylonitrile) by American
Cyanamid Co.
APPLICATIONS:
Biochemistry Respiratory action similar to that of hydrogen cyanide.
ModeofactionFumigant insecticide Uses Fumigant insecticide (ca. 510 g/m3) for
the control of pests in living areas and warehouses, machines in milling, baking, and food
processing. Formulation types TC.
PRODUCTS:
Discontinued products VCN* (Stauffer); Ventox* (Detia Degesch).
ANALYSIS:
In air, by absorption of the fumes in a measured quantity of air in an alkaline solution of
laurylmercaptan in isopropanol; the mercaptan is introduced at the double bond. Oxidation
of excess mercaptan to the disulfide with iodine solution and back-titration of the unused
acrylonitrile 3
iodine or electrophotometric determination (J. Haslam & G. Newlands Analyst, 1955,

80, 50). Residues: cyanogen bromide, formed by the action of bromine (in uv light) on
acrylonitrile generated in a nitrogen stream, forms a dye with benzidine-pyridine which
can be determined colorimetrically (Man. Pestic. Residue Anal., 120). For gc determination
see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 259260. For spectrophotometric
determination of the pyridine-acrylonitrile complex see M. E. Hall & J. W. Stevens
(Anal. Chem. 1977, 49, 22772279). Methods reviewed by J. L. Daft in Comp. Anal. Profiles,
Chapter11.
EHC 28 (1983). JMPR Evaln. 5 (1965). HSG 1 (1986). ICSC 0092 (2001). CICAD 39 (2002).
IARC 71 (1999).
IARC Class 2B
Oral Acute oral LD50 for rats 93 mg/kg. Skin and eye Liquid acrylonitrile permeates
through the skin. Inhalation Exposure to air containing 635 and 110 ml/m3 is lethal
to rats and dogs, respectively, within 4 hours. ADI/RfD (JMPR) No ADI [1965]; (EPA)
RfD0.01 mg/kg b.w. [1993]. Other It may be a carcinogen. Toxicity Class WHO (a.i.) FM.
ECClassification F; R11| R45| T; R23/24/25| Xi; R37/38, R41| R43| N; R51, R53| concn.
dep.
ECOTOXICOLOGY:
Bees Toxicity to bees not significant.
Details PM5, p. 3.
afidopyropen
Insecticide
N
O O
OH
CH3
O
H O
H3 C
HO H O
H2C CH3
O
O
NOMENCLATURE:
Common name afidopyropen (pa ISO)
IUPACname [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropylcarbonyloxy)-
4 afidopyropen
1,2,3,4,4a,5,6,6a,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-py-
ridyl)-11H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate
Chemical Abstracts name [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)
oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-
11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl
cyclopropanecarboxylate CASRN[915972177] DevelopmentcodesME5343
SmilescodeO=C(OC(C1=CN=CC=C1)=C2)C3=C2O[C@@]([C@@H](O)C4)(C)
[C@@]([C@H]3O)([H])[C@]5(C)[C@@]4([H])[C@](C)(COC(C6CC6)=O)[C@@H]
(OC(C7CC7)=O)CC5
PHYSICAL CHEMISTRY: Mol. wt. 593.7 M.f. C33H39NO9
AKH-7088
Herbicide
CH2OCH3
Cl C NOCH2CO2CH3
F3C O NO2
NOMENCLATURE:
IUPACname methyl (EZ)-1-[5-(2-chloro-,,-trifluoro-p-tolyloxy)-2-nitrophenyl]-2-
methoxyethylideneamino-oxyacetate
Chemical Abstracts name methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-
2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate CASRN[104459827]
DevelopmentcodesAKH-7088 SmilescodeCOCC(=NOCC(=O)OC)
c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 476.8 M.f. C19H16ClF3N2O7 Form Colourless
crystals. M.p.57.758.1C Solubility In water 1 mg/l (20C). In dichloromethane >50%,
toluene 15% (both 20C).
COMMERCIALISATION:
History Discovered in 1984 by Asahi Chemical Industry Co. Ltd. Reported by Y. Hayashi
etal. (Proc. Br. Crop Prot. Conf. Weeds, 1989, 1, 5358).
APPLICATIONS:
Biochemistry (E)- and (Z)- isomers show similar biological activity. Uses Post-emergence
control of broad-leaved weeds, including velvetleaf, cockleburs, and Jimson weed, in soya
beans, at 0.10.2 kg/ha.
Oral Acute oral LD50 for rats 5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats
2000 mg/kg. Moderate skin irritation; non-irritating to eyes (male rabbits). Other Non-
mutagenic in the Ames test.
AKH-7088 5
aldimorph
Fungicide
FRAC5, G2; SBI class II, amine: morpholine
NOMENCLATURE:
Common name aldimorphe ((m) F-ISO); aldimorph (BSI, E-ISO)
IUPACname 4-alkyl-2,5 (or 2,6) -dimethylmorpholine, mixed compounds where the
alkyl substituent may be octyl, decyl, dodecyl, tetradecyl or hexadecyl and where the main
component is 4-dodecyl-2,6-dimethylmorpholine
Chemical Abstracts name aldimorph CASRN[91315150]
DevelopmentcodesB 8243
PHYSICAL CHEMISTRY: Mol. wt. 283.5 M.f. C18H37NO (main component) Form
Colourless liquid. M.p.27 to 19C B.p. 110140C /0.1 mbar V.p. 5.5 101 mPa
(21.8C) Solubility In water c.20 mg/l (25C). Stability Very stable between pH 3 and
pH 10. Stable to light. On heating abovec.60C, gives a weak brown coloration.
COMMERCIALISATION:
Manufacturers Hermania
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor, by inhibition of sterol reduction (sterol-
14-reductase) and isomerisation (8 to 7-isomerase). ModeofactionSystemic,
long-term, also curative action. Absorbed through leaves and roots. Inhibits formation
of haustoria in Erysiphe graminis. Uses Controls mildew on spring and winter barley.
Formulation types EC.
PRODUCTS:
Discontinued products Falimorph* (Fahlberg-List).
ANALYSIS:
Product analysis by acidimetric titration in non-aqueous medium. Residues by
extraction wth methanol, transfer to hexane, column chromatographic clean-up on
aluminium oxide, and colorimetric determination at 540 nm of coloured substances
released by hydrochloric acid from the methyl orange-active ingredient salt.
EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Oral Acute oral LD50 for rats >3000 mice 9700 mg/kg. Skin and eye Dermal LD50 for
guinea pigs 1430 mg/kg. Skin irritant. NOEL In 90 d feeding trials on rats, highest dose
without activity was 2 mg/kg b.w. daily. ADI/RfD (BfR) 0.01 mg/kg b.w. [1991]
Other Possible teratogen.
6 aldimorph
ECOTOXICOLOGY:
Fish LC50 (96 h) for carp 2.83, salmon 0.38 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants The a.i. content in barley and wheat decreases from 18 mg/kg at application to 0.14
mg/kg after 30 d and 0.1 mg/kg after 45 and 57 d.
aldoxycarb
Acaricide, insecticide, nematicide
IRAC1A
CH3 NHCH3
CH3SO2 C CH N O C
CH3 O
NOMENCLATURE:
Common name aldoxycarb (BSI, E-ISO, ANSI, ESA); aldoxycarbe ((m) F-ISO)
IUPACname 2-mesyl-2-methylpropionaldehyde O-methylcarbamoyloxime; 2-methyl-2-
methylsulfonylpropionaldehyde O-methylcarbamoyloxime
Chemical Abstracts name 2-methyl-2-(methylsulfonyl)propanal O-[(methylamino)
carbonyl]oxime Other names aldicarb sulfone; sulfocarb CASRN[1646884]
DevelopmentcodesUC 21 865 SmilescodeCNC(=O)ON=CC(C)(C)S(=O)(=O)C
PHYSICAL CHEMISTRY: Mol. wt. 222.3 M.f. C7H14N2O4S Form White crystalline
powder with a sulfurous odour. M.p.140142C V.p. 12 mPa (25C) Henry 2.67
104 Pa m3 mol1 (calc.) Solubility In water c.10 g/l (25C). In chloroform 32, acetonitrile
74, methanol 30, dichloromethane 41, acetone 50 (all in g/l). Stability Stable, but
decomposition occurs above 140C. Rapidly hydrolysed in acidic or alkaline media.
COMMERCIALISATION:
History Insecticide and nematicide reported by M. H. J. Weiden etal. (J. Econ. Entomol.,
1965, 58, 154). Introduced by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
Patents US 3217037 Manufacturers Rhne-Poulenc
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic; taken up through
roots. Uses Control of aphids, thrips, mites, nematodes, leafhoppers and other pests on
cotton, tobacco, peanuts, maize, potatoes, cole crops and vegetables. Could be applied as
a soil treatment, foliar spray, seed dressing or transplant water treatment. Phytotoxicity
Soya beans and french bean seedlings are not tolerant. Formulation types WP; GR;
SC; FS. Compatibility Not fully known, but has been found to be compatible with most
common herbicides, insecticides, nematicides and fungicides used on tobacco.
PRODUCTS:
Discontinued products Standak* (Rhne-Poulenc).
aldoxycarb 7
ANALYSIS:
Product analysis by i.r. spectrometry (CIPACHandbook, 1980, 1A, 1094). Residues
determined by glc with FPD (R. T. Krause, J. Assoc. Offic. Anal. Chem., 1980, 63, 1114;
R. R. Romine, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 147; J. H. Smelt etal., loc. cit.).
In drinking water by rplc and fluorimetry of liberated methylamine (Environ. Chem. Methods).
EHC 64 (1986); a review of carbamate pesticides in general.
Oral Acute oral LD50 for male rats 21.4 mg/kg. Skin and eye Acute percutaneous LD50
for rats 1000, rabbits 200 mg/kg. No skin or eye irritation in standard tests. Inhalation
LC50 (4 h) for rats 0.14 mg/l air (dust). NOEL In life-span feeding trials, NOEL for mice
9.6, rats 2.4 mg/kg. ADI/RfD (EPA) 0.001 mg/kg b.w. [1993]. Other No teratogenic,
reproductive or mutagenic effects observed. Toxicity Class WHO (a.i.) Ib EPA
(formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 33.5 mg/kg. Dietary LC50 (5 d) for mallard ducks
>10000 mg/kg diet, bobwhite quail 5706 mg/kg diet. Fish LC50 (96 h) for trout 40, bluegill
sunfish 55.5 mg/l. Bees Low toxicity to bees.
ENVIRONMENTAL FATE:
Animals Degradation in animals is by hydrolysis of the carbamate ester to aldoxycarb
oxime, and elimination of the methylcarbamate group to give aldoxycarb nitrile.
Plants Degradation in plants is the same as in animals. Soil/Environment See aldicarb.
aldrin
Insecticide
IRAC2A
Cl
Cl Cl Cl
Cl Cl
NOMENCLATURE:
Common name HHDN (for pure material) (BSI, E-ISO, F-ISO, JMAF; exception USA);
aldrin (for material containing 95% HHDN) (BSI, E-ISO, ESA, JMAF); aldrine (for material
containing 95% HHDN) ((m) F-ISO)
IUPACname (1R,4S,4aS,5S,8R,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-
1,4:5,8-dimethanonaphthalene; 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-exo-1,4-
endo-5,8-dimethanonaphthalene
Chemical Abstracts name (1,4,4a,5,8,8a)-1,2,3,4,10,10-hexachloro-
1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene CASRN[309002]
8 aldrin
ECno2062158 DevelopmentcodesCompound 118 (Hyman)

SmilescodeClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 364.9 M.f. C12H8Cl6 Form Pure HHDN is a
colourless crystalline solid; aldrin is a tan to dark brown waxy solid. M.p.104104.5C
(HHDN); (aldrin 4960C) B.p. 145C /2 mmHg V.p. 8.6 mPa (20C) Solubility In
water 0.027 mg/l (27C). In acetone, benzene and xylene >600 g/l (27C). Stability
Thermally stable up to 200C. Stable between pH 4 and 8. Reacts with concentrated acids
and phenols in the presence of oxidising agents to give dieldrin.
COMMERCIALISATION:
History Insecticide reported by C. W. Kearns etal. (J. Econ. Entomol., 1949, 42, 27).
Introduced by J. Hyman & Co. and by Shell International Chemical Co., Ltd. Patents US
2635977 (to Hyman)
APPLICATIONS:
Biochemistry Antagonist of the GABA receptor-chloride channel complex.
ModeofactionNon-systemic insecticide with contact, stomach, and respiratory action.
Uses Control of soil-dwelling insects including termites and ants at 0.55.0 kg/ha. Also
used for wood preservation. Formulation types DP; EC; WP; GR.
PRODUCTS:
Discontinued products Aldrex* (Shell); Octalene* (Sandoz).
ANALYSIS:
TC and formulation analysis by i.r. spectrometry (CIPACHandbook, 1983, 1B, 1706;
AOACMethods, 18th Ed., 961.05), by tlc (ibid., 972.05), by potentiometric titration of
liberated chloride ion (CIPACHandbook, 1994, F, 190), or by glc. Residues determined by glc,
tlc or paper chromatography (AOACMethods, 18th Ed., 970.52), or by glc with ECD (Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 268; Analyst (London), 1979, 104, 425; P.A.Greve &
W. B. F. Grevenstuk, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1115; G. M. Telling,
J. Chromatogr., 1977, 137, 405; M. A. Luke et al., J. Assoc. Off. Anal. Chem., 1981, 64, 1187). See
also Pestic. Anal. Man., I, 208, 303, 503. In drinking water by glc with ECD (AOACMethods,
18th Ed., 990.06).
EHC 91 (1989). JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. 29 (1977). HSG 21
(1989). PDS 41 (1979). ICSC.774 (1998). IARC 5 (1974); Suppl. 7 (1987).
EU Status (1107/2009) Considered to be outside the scope of the Directive; already
banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 3
Oral Acute oral LD50 for rats 3867, guinea pigs 33, rabbits 5080, dogs 6595 mg/kg.
Skin and eye Acute percutaneous LD50 for rabbits 1525, rats 98 mg/kg. Toxic by skin
absorption. NOEL LOAEL 0.025 mg/kg b.w. (EPA IRIS) ADI/RfD (JMPR) 0.0001 mg/kg
b.w. (PTDI) [1994] (aldrin +dieldrin); (EPA) cRfD 0.00003 mg/kg b.w. [1988].
Water GV 0.03 ;g/l (sum of aldrin+dieldrin). Other Because aldrin is rapidly epoxidised
aldrin 9
in living tissue, forming dieldrin (q.v.), the long term toxicology of dieldrin to laboratory
animals can be regarded as representative of aldrin. Toxicity Class WHO (a.i.) Ib EPA
(formulation) I ECClassification T; R24/25, R48/24/25| R40| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 6.59, mallard 52 mg/kg. Fish LC50 (24 h) 0.018
0.089 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In living organisms, aldrin is rapidly epoxidised to dieldrin (q.v.).
Soil/Environment In soil and water, undergoes epoxidation to dieldrin (q.v.). Details
PM8, Entry 00120.
allidochlor
Herbicide
NOMENCLATURE:
Common name allidochlor (BSI, E-ISO); alidochlore ((m) F-ISO); CDAA (WSSA, JMAF)
IUPACname N,N-diallyl-2-chloroacetamide
Chemical Abstracts name 2-chloro-N,N-di-2-propenylacetamide CASRN[93710]
ECno2022707 DevelopmentcodesCP 6343 (Monsanto)
SmilescodeClCC(=O)N(CC=C)CC=C
PHYSICAL CHEMISTRY: Mol. wt. 173.6 M.f. C8H12ClNO Form Amber-coloured oil.
B.p. 74C /0.3 mmHg V.p. 1250 mPa (20C) Kow logP = 0.97 (Agchem. Desk Ref.) S.g./
density 1.088 (25C) Solubility In water 20 g/kg (25C). In chlorobenzene, chloroform,
cyclohexanone, ethanol, and xylene >500 g/kg (25C); in hexane >200 g/kg (36C).
Stability Stable to uv light; decomposes at 125C.
COMMERCIALISATION:
History Herbicide reported by P. C. Hamm & A. J. Speziale (J. Agric. Food Chem., 1956, 4,
518). Introduced by Monsanto Co. Patents US 2864683
APPLICATIONS:
Biochemistry Inhibition of cell respiration. ModeofactionSelective herbicide Uses A
selective pre-em. herbicide used to control annual grasses and certain broad-leaved weeds
in beans (various types), cabbages, celery, certain fruits, maize, onions, certain ornamentals,
sugar cane and sweet potatoes. Incorporated into soil after pre-em. application; also used
post-em. and absorbed by cotyledons of grass seedlings. Formulation types EC; GR.
PRODUCTS:
Discontinued products Randox* (Monsanto); Discontinuedmixtures Randox-T*
(+trichlorobenzyl chloride) (Monsanto).
ANALYSIS:
Product and residue analysis is by glc.
10 allidochlor
Oral Acute oral LD50 for rats 700 mg/kg. Skin and eye Acute percutaneous LD50 for
rabbits 830 mg tech./kg. Corrosive to skin and eyes (rabbits). NOEL In 90 d feeding
trials, no adverse effect observed in rats and dogs at 200 mg/kg diet (highest rate tested).
Toxicity Class WHO (a.i.) II ECClassification Xn; R21/22| Xi; R36/38| N; R51, R53
ECOTOXICOLOGY:
Fish LC50 for rainbow trout 2.0 mg/l. Bees Not toxic to bees when used as prescribed.
ENVIRONMENTAL FATE:
Plants In plants, it is readily metabolised to glycollic acid and diallylamine.
Soil/Environment Rapid hydrolytic cleavage of chlorine atom with formation of water-
soluble metabolites. There is oxidative attack on the allyl group. Glycolic acid is also a
metabolite. Loss from soil is mainly by microbial activity, but soil incorporation is needed
because of its volatility. Duration of activity 36 weeks, depending on soil.
allyl alcohol
Herbicide
CH OH
H2C CH2
NOMENCLATURE:
Common name allyl alcohol (BSI, ISO, accepted in lieu of common name)
IUPACname allyl alcohol; prop-2-en-1-ol
Chemical Abstracts name 2-propen-1-ol CASRN[107186] ECno2034707
PHYSICAL CHEMISTRY: Mol. wt. 58.08 M.f. C3H6O Form Colourless, mobile liquid
with a pungent odour. M.p.forms a glass at 190C B.p. 96.9C V.p. 2.31 106 mPa
(20C)
S.g./density 0.8535 at 20C Solubility Miscible with water and common organic
solvents. Stability Polymerises on storage and therefore requires the addition of a
stabiliser. Stable in uv light. F.p. 32C (open cup)
COMMERCIALISATION:
History Its experimental use as a herbicide first reported in 1950.
APPLICATIONS:
ModeofactionInhibits germination. Uses Herbicide for control of weed and grass
seeds. Applied to nursery, forestry, vegetable, tobacco, and other seeds beds, at 85170
g in 50000100000 l water/ha. Also for the partial sterilisation of glasshouse soil (E. M.
Emmert & J. E. Klinker, Ky. Agric. Exp. Stn. Prog. Rep., 1950) at 18.4 g in 6.1 l water/m2 of soil.
Formulation types TC.
ANALYSIS:
allyl alcohol 11
Product analysis by measurement of the bromine added across the double-bond or

acetylation of the hydroxyl group in the presence of pyridine. For a polarographic
determination see M. Jaworski and J. Bogaczek (Chem. Anal. (Warsaw) 1969, 14, 12471251),
reported in Fresenius Z. Anal. Chem. 1971, 257, 70. It may be detected by trapping in water
or sulfuric acid and oxidising to acrylaldehyde by chromic-sulfuric acid. For detection of
residues in soil before sowing, the biological cress root test is mostly applied.
ICSC 0095 (2000). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD50 for rats 64, mice 85 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits 89 mg/kg; absorbed rapidly through the skin. Lachrymatory and intensely
irritating to skin and mucous membranes. Inhalation High inhalation toxicity. NOEL
Highest oral dose without activity for male and female rats 4.8 and 6.2 mg/kg daily (15 w).
ADI/RfD (EPA) cRfD 0.005 mg/kg b.w. [1989]. Other Maximum acceptable concentration
in work-place atmosphere over an 8-hour work period 5 mg/m3. Toxicity Class WHO
(a.i.) Ib ECClassification R10| T; R23/24/25| Xi; R36/37/38| N; R50
ECOTOXICOLOGY:
Fish Toxic to fish. Bees Not toxic to bees when used as prescribed.
ENVIRONMENTAL FATE:
Soil/Environment Metabolism not known. It disappears for the most part through
evaporation. Duration of activity 310 days depending on temperature, soil type, and
humidity.
Details PM6, p. 9.
allyxycarb
Insecticide
NOMENCLATURE:
Common name allyxycarb (BSI, E-ISO); allyxycarbe (F-ISO); APC (JMAF)
IUPACname 4-diallylamino-3,5-xylyl methylcarbamate
Chemical Abstracts name 4-(di-2-propenylamino)-3,5-dimethylphenyl methylcarbamate
CASRN[6392467] DevelopmentcodesBayer 50 282; A 546
SmilescodeCNC(=O)Oc1cc(C)c(N(CC=C)CC=C)c(C)c1
PHYSICAL CHEMISTRY: Mol. wt. 274.4 M.f. C16H22N2O2
COMMERCIALISATION:
History Insecticide introduced by Bayer AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor.
12 allyxycarb

EHC 64 (1986; a review of carbamate pesticides in general).
Toxicity Class WHO (a.i.) O
Details PM4, p. 10.
alorac
NOMENCLATURE:
Common name alorac (BSI, E-ISO, (m) F-ISO)
IUPACname (Z)-perchloro-4-oxopent-2-enoic acid;
(Z)-2,3,5,5,5-pentachloro-4-oxopent-2-enoic acid
Chemical Abstracts name (Z)-2,3,5,5,5-pentachloro-4-oxo-2-pentenoic acid
CASRN[19360022] SmilescodeOC(=O)/C(=C(/Cl)\C(=O)C(Cl)(Cl)Cl)/Cl;
without stereochemistry:OC(=O)C(=C(Cl)C(=O)C(Cl)(Cl)Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 286.3 M.f. C5HCl5O3
COMMERCIALISATION:
History Plant growth regulator.
ametridione
Herbicide
NOMENCLATURE:
Common name am(tridione) ((m) F-ISO); ametridione (BSI, E-ISO)
IUPACname 1-amino-6-ethylthio-3-neopentyl-1,3,5-triazine-2,4(1H,3H)-dione
Chemical Abstracts name 1-amino-3-(2,2-dimethylpropyl)-6-(ethylthio)-1,3,5-triazine-
2,4(1H,3H)-dione CASRN[78168931] DevelopmentcodesBAY SSH 0860
SmilescodeCCSc1nc(=O)n(CC(C)(C)C)c(=O)n1N
PHYSICAL CHEMISTRY: Mol. wt. 258.3 M.f. C10H18N4O2S
COMMERCIALISATION:
History Herbicide evaluated by Bayer AG.
amibuzin
Herbicide
NOMENCLATURE:
Common name amibuzine ((f) F-ISO); amibuzin (BSI, E-ISO)
IUPACname 6-tert-butyl-3-dimethylamino-4-methyl-1,2,4-triazin-5(4H)-one
amibuzin 13
Chemical Abstracts name 3-(dimethylamino)-6-(1,1-dimethylethyl)-4-methyl-1,2,4-

triazin-5(4H)-one CASRN[76636107] DevelopmentcodesDIC 3202
SmilescodeCN(C)c1nnc(c(=O)n1C)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 210.3 M.f. C10H18N4O
COMMERCIALISATION:
History Herbicide developed by Bayer AG.
amidithion
Acaricide, insecticide
IRAC1B
NOMENCLATURE:
Common name amidiphos ((m) France); amidithion (BSI, E-ISO, (m) F-ISO, ESA, ex-ANSI)
IUPACname S-2-methoxyethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-(2-methoxyethyl)acetamide
Chemical Abstracts name S-[2-[(2-methoxyethyl)amino]-2-oxoethyl] O,O-dimethyl
phosphorodithioate CASRN[919766] DevelopmentcodesCiba 2446
SmilescodeCOCCNC(=O)CSP(=S)(OC)OC
PHYSICAL CHEMISTRY: Mol. wt. 273.3 M.f. C7H16NO4PS2
COMMERCIALISATION:
History Acaricide and insecticide (V. Dittrich & F. Bachman, Proc. Br. Insectic. Fungic. Conf.,
2nd, 1963, p. 421). Introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
EHC 63 (1986; a general review of organophosphorus insecticides).
Toxicity Class WHO (a.i.) O ECClassification Xn; R22
Details PM2, p. 16.
amidochlor
NOMENCLATURE:
Common name amidochlor (ANSI)
IUPACname N-acetamidomethyl-2-chloro-2,6-diethylacetanilide
Chemical Abstracts name N-[(acetylamino)methyl]-2-chloro-N-(2,6-diethylphenyl)
acetamide CASRN[40164678] DevelopmentcodesMON 4620; CP-76 963
14 amidochlor
SmilescodeCCc1cccc(CC)c1N(CNC(=O)C)C(=O)CCl
PHYSICAL CHEMISTRY: Mol. wt. 296.8 M.f. C15H21ClN2O2
COMMERCIALISATION:
History Plant growth regulator introduced by Monsanto Co.
PRODUCTS:
Discontinued products Limit* (Monsanto).
amidothioate
IRAC1B
NOMENCLATURE:
Common name amidothioate (JMAF)
IUPACname O-2-chloro-4-methylthiophenyl O-methyl ethylphosphoramidothioate
Chemical Abstracts name O-[2-chloro-4-(methylthio)phenyl] O-methyl
ethylphosphoramidothioate CASRN[54381269] DevelopmentcodesNK-11
SmilescodeCCNP(=S)(OC)Oc1ccc(SC)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 311.8 M.f. C10H15ClNO2PS2
COMMERCIALISATION:
History Acaricide introduced by Nippon Kayaku Co., Ltd.
APPLICATIONS:
aminocarb
Insecticide
IRAC1A
NOMENCLATURE:
Common name aminocarb (BSI, E-ISO, ESA); aminocarbe ((m) F-ISO)
IUPACname 4-dimethylamino-m-tolyl methylcarbamate
Chemical Abstracts name 4-(dimethylamino)-3-methylphenyl methylcarbamate
Other names DTMC CASRN[2032599] ECno2179907
DevelopmentcodesBayer 44 646; A 363
SmilescodeCNC(=O)Oc1ccc(N(C)C)c(C)c1
PHYSICAL CHEMISTRY: Mol. wt. 208.3 M.f. C11H16N2O2 Form Colourless
crystalline solid. M.p.9394C V.p. 2.3 mPa (EPA, 1988) Solubility In water 915 mg/
kg (20C) (Agchem. Desk Ref.). Moderately soluble in aromatic solvents; soluble in polar
organic solvents.
COMMERCIALISATION:
aminocarb 15
History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch.

Opzoekingsstn. Staat Gent, 1963, 28, 758). Introduced by Bayer AG. Patents DE 1145162
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic insecticide
with contact and stomach action. Uses Mainly used against lepidopterous larvae and
other chewing insects; generally recommended at 75 g/100 l. Formulation types WP.
Compatibility Incompatible with highly alkaline pesticides.
PRODUCTS:
Discontinued products Matacil* (Bayer); Metacil* (Bayer).
ANALYSIS:
Product analysis by rplc (CIPACHandbook, 1988, D, 7) or lc (AOACMethods, 18th Ed., 985.02;
J. Assoc. Off. Anal. Chem., 1985, 68, 372, 6.A256.A30) or by uv spectroscopy (H. Niessen
& H. Frehse, Pflanz.-Nachr. Bayer (Engl. Ed.), 1963, 16, 205). Residues determined by uv
spectroscopy or by glc of a derivative (R. J. Argauer, J. Agric. Food Chem., 1969, 17, 888; E. R.
Holden et al., ibid., p.56; L. I. Butler & L. M. McDonough, ibid., 1968, 16, 403). See also Pestic.
Anal. Man., I, 302.
EHC 64 (1986; a review of carbamate pesticides in general). JMPR Evaln. 33 (1979).
ICSC 0097 (1994).
Oral Acute oral LD50 for rats 3050 mg/kg. Skin and eye Acute percutaneous LD50
for rats 275 mg/kg. NOEL In 2 y feeding trials, rats receiving 200 mg/kg diet showed no
symptom of poisoning. ADI/RfD (JMPR) No ADI [1979]. Other Acute i.p. LD50 for rats
21 mg/kg. Toxicity Class WHO (a.i.) Ib ECClassification T; R24/25| N; R50, R53
ECOTOXICOLOGY:
Bees Toxic to bees.
amiprofos-methyl
Herbicide
HRACK1 WSSA 3; phosphoroamidate
NOMENCLATURE:
Common name amiprofos-methyl (BSI, E-ISO, (m) F-ISO)
IUPACname O-methyl O-2-nitro-p-tolyl isopropylphosphoramidothioate
Chemical Abstracts name O-methyl O-(4-methyl-2-nitrophenyl) (1-methylethyl)
phosphoramidothioate Other names amiprophos-methyl CASRN[36001884]
DevelopmentcodesBAY NTN 6867; NTN 2925
SmilescodeCOP(=S)(NC(C)C)Oc1ccc(C)cc1[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 304.3 M.f. C11H17N2O4PS
16 amiprofos-methyl
COMMERCIALISATION:
History Herbicide reported by M. Aya etal. (Zasso Kenkyu, 1973, (15), p. 20). Evaluated by
Bayer AG.
APPLICATIONS:
Biochemistry Microtubule assembly inhibition.
amiton; amiton hydrogen oxalate

IRAC1B
NOMENCLATURE:
Common name amiton (BSI)
IUPACname S-2-diethylaminoethyl O,O-diethyl phosphorothioate
Chemical Abstracts name S-[2-(diethylamino)ethyl] O,O-diethyl phosphorothioate
CASRN[78535] amiton; [3734972] amiton hydrogen oxalate
DevelopmentcodesR 5158 (amiton); R 6199 (amiton hydrogen oxalate)
PHYSICAL CHEMISTRY: Mol. wt. 269.3; (oxalate 359.4) M.f. C10H24NO3PS; (oxalate
C12H26NO7PS)
COMMERCIALISATION:
History Insecticide and acaricide reported by R. Ghosh & J. F. Newman (Chem. Ind.
(London), 1955, p. 118) and by G. L. Baldit (J. Sci. Food Agric., 1958, 9, 516). Evaluated by Plant
Protection Ltd (later ICI Agrochemicals).
APPLICATIONS:
PRODUCTS:
Discontinued products Tetram* (oxalate) (ICI).
ampropylfos
Fungicide
O NH2
HO P CHCH2CH3
OH
NOMENCLATURE:
Common name ampropylfos (BSI, E-ISO, (m) F-ISO)
IUPACname (RS)-1-aminopropylphosphonic acid
ampropylfos 17
Chemical Abstracts name ()-(1-aminopropyl)phosphonic acid

CASRN[16606647] DevelopmentcodesPNL-62
SmilescodeCCC(N)P(=O)(O)O
PHYSICAL CHEMISTRY: Mol. wt. 139.1 M.f. C3H10NO3P Form White solid.
M.p.264270C V.p. 3.7 103 mPa (90C) Kow logP = 3 S.g./density 0.5 Solubility
In water 139 g/l (21C). In methanol 0.46, isopropanol 0.003, hexane, toluene,
dichloromethane, ethyl acetate, and acetone 0.0001 (all in g/l, 21C). Stability Stable 2
y (pH 47, 20C); stable >31 d
(pH 9, 25C); stable 3 d (pH 4, 100C). pKa pKa2 5.9, pKa3 10.4
COMMERCIALISATION:
History Fungicide discovered by KenoGard AB (later Rhne-Poulenc Agrochimie).
APPLICATIONS: Uses Control of covered smut, loose smut, Fusarium spp., leaf stripe,
and net blotch in barley, and leaf stripe and loose smut in oats. Formulation types SC.
PRODUCTS:
Discontinuedmixtures Ravyl* (+anthraquinone +myclobutanil) (Bayer).
ANALYSIS:
Product by hplc with uv detection at 220 nm.
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for
rats >2000 mg/kg. Non-sensitising to skin (guinea pigs). Non-irritating to skin of rabbits.
Inhalation LC50 for rats >4 mg/l air. NOEL (90 d) for rats 100 mg/kg daily (only minimal
changes at 300 mg/kg daily). In 90 d feeding trials, 0.1% PNL 62 in the diet had no effect
on dogs after 13 w treatment (effects at 0.5% were minimal and there is no evidence
of systemic or target organ toxicity). Non-teratogenic to rats at 1000 mg/kg daily. Non-
teratogenic to rabbits at 10 mg/kg daily. Other Intravenous LD50 for rats c.1250 mg/kg.
Non-mutagenic in the Ames test and other mutagenicity tests.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2000 mg/kg. Dietary LC50 for
bobwhite quail and mallard ducks >5000 mg/kg. No observed neurotoxicity to hens.
Fish LC50 (96 h) for rainbow trout, bluegill sunfish, and mirror carp >135 mg/l.
Daphnia LC50 (24 and 48 h) >100 mg/l. Algae EC50 for Selenastrum capricornutum 54 mg/l.
Worms LC50 for Eisenia foetida >1000 mg/kg.
ENVIRONMENTAL FATE:
Animals After oral administration to rats of a single dose of 200 mg ampropylfos/kg b.w.
there is a rapid absorption (about 50%) with peak concentration 1 h after dosage, and a
fast decline in a bioexponential manner with DT50 c.2 h in plasma, 50 h in blood. Similar
18 ampropylfos
decline is found after intravenous administration in rats. Whole body autoradiograms of

rats showed that 14C-labelled ampropylfos is widely distributed in tissues as well as being
taken up to some extent into bone and blood cells. There is no evidence of 14C-labelled
ampropylfos-related material crossing either the placental or blood brain barriers.
Plants Uptake of 14C-labelled ampropylfos (applied as a seed dressing formulation at a
level of 400 mg/kg seed) from seeds of winter barley is very low.
Soil/Environment Ampropylfos is strongly bound to soil. The percentage of applied
14
C-labelled ampropylfos eluted from three standard soil types was 0.61 (sand), 0.035
(loamy sand), 0.925 (sandy loam) (14C-labelled ampropylfos applied in an amount
corresponding to a field application rate of 1500 g/ha and water added equivalent to
200mm rain). Ampropylfos is readily biodegradable in freshwater to levels of 81% and 79%
within 35 days at 22.5 2.5C using unacclimatised and acclimatised inocula, respectively.
No photodegradation of ampropylfos was observed in artificial sunlight after 34 days of
continuous irradiation in pH 5, pH 7, and pH 9 buffered aqueous solutions at 25C (1 day
of artificial sunlight was equivalent to 1.25 days of natural sunlight).
anabasine
Insecticide
NOMENCLATURE:
Common name anabasine (JMAF)
IUPACname (S)-3-(piperidin-2-yl)pyridine
Chemical Abstracts name (S)-3-(2-piperidinyl)pyridine Other names 2-(3-pyridyl)
piperidine CASRN[494520]; [13078041] racemate
SmilescodeC1CCC(NC1)c2cccnc2
PHYSICAL CHEMISTRY: Mol. wt. 162.2 M.f. C10H14N2 M.p.Freezes 9C B.p. 281C
S.g./density 1.048 (20C) Solubility Miscible with water and most organic solvents.
COMMERCIALISATION:
Production Obtained, as racemic material, from Nicotiana glauca. History Insecticide
isolated in 1931 from Anabasis aphylla.
APPLICATIONS:
Biochemistry Agonist of nicotine acetylcholine receptors.
anabasine 19
anilazine
Fungicide
Cl
Cl N NH
N N
Cl
FRACM8, M; multi-site: triazine fungicide
NOMENCLATURE:
Common name anilazine (BSI, E-ISO, (f) F-ISO); triazine (JMAF)
IUPACname 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine; 2-chloro-N-(4,6-
dichloro-1,3,5-triazin-2-yl)aniline
Chemical Abstracts name 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine
CASRN[101053] ECno2029105 DevelopmentcodesB-622 (Ethyl Corp.)
SmilescodeClc1ccccc1Nc2nc(Cl)nc(Cl)n2
PHYSICAL CHEMISTRY: Mol. wt. 275.5 M.f. C9H5Cl3N4 Form Colourless to tan
crystals. M.p.159C
V.p. 8.2 104 mPa (20C) Kow logP = 3.02 (20C) Henry 2.82 105 Pa m3 mol1
(calc.) S.g./density 1.8 (20C) Solubility In water 8 mg/l (20C). In acetone 100,
chlorobenzene 60, toluene 50, xylene 40 (all in g/l, 30C). In dichloromethane 90,
isopropanol 8, hexane 1.7 (all in g/l, 20C). Stability Stable in neutral and slightly acidic
media. Hydrolysed on heating with alkalis; DT50 (22C) 730 h (pH 4), 790 h (pH 7), 22 h
(pH 9).
COMMERCIALISATION:
History Fungicide reported by C. N. Wolf etal. (Science, 1955, 121, 61). Introduced by the
Ethyl Corp. and later by Nippon Soda Co., Ltd and by Bayer AG. Patents US 2720480 (to
Ethyl Corp.) Manufacturers Bayer CropScience
APPLICATIONS:
Biochemistry Multi-site action. ModeofactionNon-systemic foliar fungicide, with
protective action. Uses Control of Septoria spp. of wheat (glume blotch and on leaves)
was the main area of use. Also used for the control of early and late blights of potatoes
and tomatoes; anthracnose in cucurbits; leaf spot diseases (Alternaria, Cercospora, and
Septoria spp.) in many crops; Helminthosporium spp. in wheat and barley; brown patch,
dollar spot, snow mould, and other diseases of turf; Botrytis, Colletotrichum, Leptosphaeria,
and Pyrenophoraspp. on many crops; etc. Also used on vegetables, ornamentals, berry fruit,
melons, water melons, coffee, and tobacco. Formulation types WP; SC. Compatibility
Incompatible with oils and alkaline materials.
PRODUCTS:
Discontinued products Dyrene* (Bayer); Kemate* (Bayer); Triazine* (Nippon Soda);
Triazin Jet* (Nippon Soda).
20 anilazine
ANALYSIS:
Product analysis by lc (AOACMethods, 18th Ed., 988.04; CIPACHandbook, 1992, E, 5) or by
hydrolysis and measurement of the chloride liberated (P. F. Kane & K. G. Gillespie, J. Agric.
Food Chem., 1960, 8, 29). Methods for determination of residues were available from Bayer.
JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. II 58 (1989).
rats >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Inhalation LC50 for rats
(4 h) >0.25 mg/l air (aerosol), (1 h) >0.7 mg/l air (dust). NOEL (2 y) for rats 2000, mice
1250 mg/kg diet; (18 mo) for dogs 40 mg/kg b.w. ADI/RfD (JMPR) 0.1 mg/kg b.w. [1989];
(EPA) 0.0004 mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) U; (WHO Recommended
Classification gives O) EPA (formulation) II ECClassification Xi; R36/38| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for Virginia quail >2000 mg/kg b.w. LC50 (5 d) for mallard ducks
>5000 mg/kg. Fish LC50 (96 h) for rainbow trout and golden orfe 0.15 mg/l. Daphnia LC50
(48 h) 0.07 mg/l. Bees Not harmful to bees at recommended application rates.
ENVIRONMENTAL FATE:
Animals Elimination is quick; almost 98% is excreted within 72 h in the urine and faeces.
Plants In plants, one or both chlorine atoms in the triazine ring are substituted by
amino or thio groups, through reaction with amino acids, peptides, coenzymes, and other
endogenous substances in the cellular system of the plant (R. G. Owens Ann. New York Acad.
Sci. 1969, 160, 114132). Soil/Environment DT50 in damp soilc.12 h. Readily degraded in
different soils.
anisuron
Herbicide
NOMENCLATURE:
Common name anisuron (BSI) IUPACname 1-(3,4-dichlorophenyl)-1-(4-
methoxybenzoyl)-3,3-dimethylurea Chemical Abstracts name N-(3,4-dichlorophenyl)-
N-[(dimethylamino)carbonyl]-4-methoxybenzamide CASRN[2689432]
SmilescodeCOc1ccc(cc1)C(=O)N(C(=O)N(C)C)c2ccc(Cl)c(Cl)c2
PHYSICAL CHEMISTRY: Mol. wt. 367.2 M.f. C17H16Cl2N2O3
COMMERCIALISATION:
History Herbicide.
anisuron 21
antu
Rodenticide
NOMENCLATURE:
Common name antu (BSI, E-ISO, (m) F-ISO, JMAF)
IUPACname 1-(1-naphthyl)-2-thiourea
Chemical Abstracts name 1-naphthalenylthiourea Other names -naphthylthiourea
CASRN[86884] ECno2017063 SmilescodeNC(=S)Nc1cccc2ccccc12
PHYSICAL CHEMISTRY: Mol. wt. 202.3 M.f. C11H10N2S Form Colourless
crystals; (tech. is a blue-grey powder). M.p.198C Solubility In water 600 mg/l (room
temperature). In acetone 24.3, triethyleneglycol 86 (both g/l, room temperature). Stability
Stable on exposure to air and to sunlight.
COMMERCIALISATION:
History Toxicity to rodents reported by C. F. Richter (J. Am. Med. Assoc., 1945, 129, 927;
Proc. Soc. Exp. Biol. Med., 1946, 63, 364). Patents US 2390848
APPLICATIONS: Uses A rodenticide specific for adult Rattus norvegicus for which the
toxic dose is
68 mg/kg. It is less toxic to other Rattus spp. and tolerance is developed in rats by
repeated administration of sub-lethal doses. Formulation types RB; CP.
ANALYSIS:
Product analysis is by reaction with silver nitrate and titration of the liberated nitric acid.
(CIPACHandbook, 1970, 1, 16; AOACMethods, 18th Ed., 948.03, see 10th Ed., 4.132). Residues
determined by colorimetry of a derivative (E. Bremais & K. G. Bergner, Pharm. Zentralhalle,
1950, 89, 115).
ICSC.973 (2000). IARC 30 (1983); suppl. 7 (1987).
IARC Class 3
Oral Acute oral LD50 for Norwegian rats 68 mg/kg; less toxic for other rat species;
surviving rats develop tolerance. Acute oral LD50 for monkeys 4250, dogs 38 mg/kg.
Relatively safe for domestic animals; induces vomiting in dogs. Pigs are very sensitive.
Very low human toxicity. Other Naphthylamines, present as impurities, are carcinogenic.
Toxicity Class WHO (a.i.) Ib ECClassification T+; R28| R40
ECOTOXICOLOGY:
Birds Chickens are very sensitive.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 40% is eliminated within 20 h. Metabolised
by lung and liver microsomal preparations into 1-naphthylurea and sulfur.
22 antu
aramite
Acaricide
NOMENCLATURE:
Common name aramite (JMAF)
IUPACname 2-(4-tert-butylphenoxy)-1-methylethyl 2-chloroethyl sulfite
Chemical Abstracts name 2-chloroethyl 2-[4-(1,1-dimethylethyl)phenoxy]-1-
methylethyl sulfite CASRN[140578] Developmentcodes88-R
SmilescodeCC(COc1ccc(cc1)C(C)(C)C)OS(=O)OCCCl
PHYSICAL CHEMISTRY: Mol. wt. 334.9 M.f. C15H23ClO4S
COMMERCIALISATION:
History Acaricide reported by W. D. Harris & J. W. Zukel (J. Agric. Food Chem., 1954, 2, 140).
Introduced by Uniroyal Chemical Co., Inc.
PRODUCTS:
Discontinued products Aramite* (Uniroyal); Niagaramite* (FMC).
ANALYSIS:
Residues determined colorimetrically (AOACMethods, 18th Ed., 959.10, see 12th Ed.,
29.06729.071).
IARC 5 (1974). EU Status (1107/2009) Never notified to the EU.
IARC Class 2B Toxicity Class WHO (a.i.) O
Details PM3, p. 73.
arsenous oxide
Rodenticide
NOMENCLATURE:
Common name arsenious acid (JMAF); arsenous oxide (E-ISO, accepted in lieu of a
common name); oxyde arsenieux (F-ISO, accepted in lieu of a common name.)
IUPACname diarsenic trioxide; arsenic trioxide
Chemical Abstracts name arsenic oxide (As2O3) Other names arsenious oxide;
white arsenic CASRN[1327533] ECno2154814
Smilescodeo1[as]2o[as]3o[as]1o[as](o2)o3
PHYSICAL CHEMISTRY: Mol. wt. 395.7 M.f. As4O6 Form Colourless solid which
exists in rhombic, octahedral and amorphous forms. The amorphous form is unstable,
reverting to the octahedral. M.p.272C, subliming 125150C (octahedral); 312C
(rhombic) V.p. 8.8 kPa (312C) (rhombic form) Solubility In water 17 g/l (16C).
Practically insoluble in chloroform, diethyl ether, ethanol. Stability Stable in air but
oxidised slowly in acid media. Dissolves in alkali to form arsenites.
arsenous oxide 23
COMMERCIALISATION:
History Used as a rodenticide since the 16th century.
APPLICATIONS: Uses Used in baits to control Rattus norvegicus, R. rattus and Mus
musculus. It has also been used as a sheep dip to control ectoparasites. Formulation
types PA .
ANALYSIS:
Product analysis by titration with iodine (WHO Specifications Insectic. (2nd Ed.). Residues
determined by atomic absorption spectroscopy (AOACMethods, 14th Ed., 25.00125.007)
by colorimetry (ibid., 25.04125.055) or by the Gutzeit method (ibid., 25.045; 12th Ed.,
25.00625.009).
EHC 224 (2001). HSG 70 (1992). ICSC.378 (1997). IARC 23 (1980), Suppl 7 (1987).
IARC Class 1 (evaluation applies to arsenic compounds as a whole, not necessarily to all
individual compounds within the group)
Oral Acute oral LD50 for rats 180200 mg a.i. (in carbohydrate or protein)/kg, 300 mg (in
bacon fat)/kg, 20 mg (in aqueous solution)/kg (E. Packman et al., J. Agric. Food Chem., 1961,
9, 271); for mice 34.463.5 mg/kg (J. W. E. Harrison, AMA Arch. Ind. Health, 1958, 17, 118).
Other It is extremely toxic to man, the minimum lethal dose is 2 mg/kg (H. O. Calvery,
J. Am. Med. Assoc., 1938, 111, 1722). It is non-cumulative and is eliminated from the animal
body in 742 d. Evidence of carcinogenicity in humans. Toxicity Class WHO (a.i.) Ia
(sodium arsenite Class Ib) ECClassification R45| T+; R28| C; R34| N; R50, R53
asomate
Chemosterilant
S Me
H3C S N
N Me
CH3 S S
As
S S
N
H3C CH3
NOMENCLATURE:
IUPACname arsinetriyl tris(dimethyldithiocarbamate); 1-{[bis(dimethylthiocarbamoyls
ulfanyl)arsanyl]sulfanyl}-N,N-dimethylmethanethioamide; tris(dimethylthiocarbamoylthio)
arsine Chemical Abstracts name N,N-dimethylcarbamodithioic acid anhydrosulfide with
arsenotrithious acid (3:1); tris(dimethyldithiocarbamato)arsenic
24 asomate
Other names TDDA; TTCA CASRN[3586605]

SmilescodeS=C(N(C)C)S[As](SC(N(C)C)=S)SC(N(C)C)=S
PHYSICAL CHEMISTRY: Mol. wt. 435.6 M.f. C9H18AsN3S6 Form Yellow-green
crystals.
APPLICATIONS:
ModeofactionPreventative and curative fungicide. Uses Used on apples and pears,
powdery mildew of cucumber, grapes etc. Also for rice blast. Formulation types WP.
Oral Acute oral LD50 for rats 335-370 mg/kg. Skin and eye Strong skin irritant.
athidathion
Insecticide
IRAC1B
NOMENCLATURE:
Common name athidathion (BSI, E-ISO, (m) F-ISO)
IUPACname O,O-diethyl S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl
phosphorodithioate; 2-diethoxyphosphinothioylthiomethyl-5-methoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name O,O-diethyl S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)
methyl] phosphorodithioate CASRN[19691806] DevelopmentcodesG 13 006
SmilescodeCCOP(=S)(OCC)SCn1nc(OC)sc1=O
PHYSICAL CHEMISTRY: Mol. wt. 330.4 M.f. C8H15N2O4PS3
COMMERCIALISATION:
History Insecticide reported by K. Rfenacht (Helv. Chim. Acta, 1968, 51, 518). Introduced
by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
PRODUCTS:
Discontinued products Deltacron* (Geigy).
atraton
Herbicide
NOMENCLATURE:
Common name atraton (BSI, E-ISO, (f) F-ISO); atratone ((f) France, former name (BSI))
IUPACname N2-ethyl-N4-isopropyl-6-methoxy-1,3,5-triazine-2,4-diamine
atraton 25
Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylethyl)-1,3,5-triazine-2,4-

diamine CASRN[1610179] DevelopmentcodesG 32 293
SmilescodeCCNc1nc(NC(C)C)nc(OC)n1
PHYSICAL CHEMISTRY: Mol. wt. 211.3 M.f. C9H17N5O M.p.9496C V.p. 3.8 mPa
(20C) Henry 4.46 104 Pa m3 mol1 (calc.) Solubility In water 0.18% (20C). Soluble
in ketones, esters, ether, alcohols and other organic solvents. Stability Stable in neutral,
weakly acidic and weakly basic media. Hydrolysed by warm acids and alkalis.
COMMERCIALISATION:
History Herbicide reported by E. Knsli (Phytiatr.-Phytopharm., 1958, 7, 81). Introduced by
J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
Biochemistry Interferes with photosynthesis and other enzymic processes. Uses
Selective herbicide used to protect sugar cane. Was also a component in total herbicide
mixtures. Formulation types WP; EC.
ANALYSIS:
Product by extraction with ether and titration of one amino group with perchloric acid
(Anal. Methods Pestic. Plant Growth Regul., 4, 28, 173). Residues by extraction with methylene
chloride, hydrolysis with 0.1 N sulphuric acid, and spectrophotometric determination
of the hydroxy derivative at 240 nm (Anal. Methods Pestic. Plant Growth Regul. 4, 28). For
determination by tlc, spectrophotometry, and gc, see Man. Pestic. Residue Anal., 6AC. For
gc determination with prometon as internal standard, see Anal. Methods Pestic. Plant Growth
Regul. 1972, 6, 597599. In drinking water by glc with NPD (AOACMethods, 18th Ed.,
991.07).
Oral Acute oral LD50 for rats 14652400, mice 905 mg/kg. Skin and eye Feeding 50%
atraton to rats at 10 and 200 mg/kg b.w. for 90 d produces no signs of illness.
ENVIRONMENTAL FATE:
Soil/Environment Replacement of the methoxy group at C-2 by hydrolysis via the
hydroxyl group. Dealkylation of the amino substituents at C-4 and C-6. Possibly opening of
the triazine ring.
azafenidin
Herbicide
CH
C
O O CH2
N
N Cl
N
Cl
26 azafenidin
HRACE WSSA 14; triazolinone

NOMENCLATURE:
Common name azaf(nidine) ((f) F-ISO); azafenidin (BSI, E-ISO)
IUPACname 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-
triazolo[4,3-a]pyridin-3(2H)-one
Chemical Abstracts name 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-
tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one CASRN[68049832]
DevelopmentcodesR6447; DPX-R6447; IN-R6447 (all DuPont)
SmilescodeClc1cc(Cl)c(cc1OCC#C)n2nc3CCCCn3c2=O
PHYSICAL CHEMISTRY:
Composition Tech. isc.97% pure. Mol. wt. 338.2 M.f. C15H13Cl2N3O2 Form White
powdered solid; (tech. is a rust-coloured solid with a pungent odour). M.p.168168.5C
V.p. 1 106 mPa (20C) Kow logP = 2.7 S.g./density 1.4 (20C) Solubility In water 16
ppm (pH 7). Stability Stable to hydrolysis; aqueous photolysis DT50 c.12 h.
COMMERCIALISATION:
History Evaluated by E. I. du Pont de Nemours & Co. Reported by L. Amuti etal. (Proc. Br.
Crop Prot. Conf. Weeds 1997, 1, p. 59).
Manufacturers DuPont
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionAbsorbed through
the roots and shoots. Weakly xylem or phloem mobile, hence has limited post-emergence
activity. However, it improves the efficacy of other post-emergence herbicides, such as
glyphosate, and increases the speed of action of contact herbicides. Uses Intended for
use as a pre-emergence, and, in mixture, post-emergence, herbicide in citrus, grapes, olives,
sugar cane and other perennial crops; active on both annual and perennial weeds, and
applied at 240 g/ha. Formulation types WG .
PRODUCTS:
Discontinued products Evolus* (Europe) (DuPont); Milestone* (USA) (DuPont).
EU Status (1107/2009) Not approved, 2002/949/EC.
rabbits >2000 mg/kg. Not an eye or skin irritant. Not a skin sensitiser. Inhalation LC50 for
rats >5.3 mg/l. NOEL (90 d) for male and female rats 50, male mice 50, female mice 300,
dogs 10 ppm. Other Negative in Ames test. ECClassification T; R48/22| R61, R62| N;
R50, R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. LC50 (8 d) for
bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for rainbow trout 33,
bluegill sunfish 48 mg/l. Daphnia EC50 (48 h) 38 mg/l. Algae EC50 (120 h) for Selenastrum
capricornutum 0.94 ;g/l. Bees LD50 (oral) >20 g/bee; (contact) >100 g/bee.
azafenidin 27
ENVIRONMENTAL FATE:
Soil/Environment Degrades in soil by microbial and photolytic processes. In the field, in
a range of 4 soils, mean DT50c.25 d, mean DT90c.169 d. Mean Koc 298; there was minimal
movement in soil column leaching studies and azafenidin is not expected to leach into
groundwater. It is expected to dissipate rapidly through photolysis in natural waters.
aziprotryne
Herbicide
CH3S N NHCH(CH3)2
N N
N3
NOMENCLATURE:
Common name aziprotryne (BSI, E-ISO, (f) F-ISO); aziprotryn (USA)
IUPACname 4-azido-N-isopropyl-6-methylthio-1,3,5-triazin-2-ylamine
Chemical Abstracts name 4-azido-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazin-2-
amine CASRN[4658280] DevelopmentcodesC 7019
SmilescodeCSc1nc(NC(C)C)nc(N=[N]=[N])n1
PHYSICAL CHEMISTRY: Mol. wt. 225.3 M.f. C7H11N7S Form Colourless crystalline
powder. M.p.94.595.5C V.p. 0.267 mPa (20C) Henry 1.09 103 Pa m3 mol1
dichloromethane 37, ethyl acetate 12, isopropanol 14, benzene 4 (all in g/kg, 20C).
Stability Stable in neutral and slightly acidic media. Hydrolysed slowly in slightly alkaline
media.
COMMERCIALISATION:
History Herbicide reported by D. H. Green etal. (C. R. Journ. Etud. Herbic. Conf.
COLUMA, 4th, 1967, 1, 1). Introduced by Ciba AG (later Novartis Crop Protection AG).
Patents BE 656233; GB 1093376 Manufacturers Novartis
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor
site. ModeofactionSelective herbicide, absorbed through the roots and foliage. Uses
Control of a wide range of annual broad-leaved weeds and some grasses in brassicas
(except cauliflowers), onions, leeks, garlic, shallots, fennel, peas, beans, black salsify, and
oilseed rape. Applied pre- or post-emergence. Phytotoxicity Phytotoxic to cauliflowers.
Formulation types WP.
PRODUCTS:
Discontinued products Brasoran* (Novartis); Mesoranil* (Ciba-Geigy).
28 aziprotryne
ANALYSIS:
Product analysis by glc. Residues determined by glc using MCD.
for rats >3000 mg/kg. Mild eye irritant; non-irritating to skin. Inhalation LC50 (6 h) for rats
>0.208 mg/l. NOEL (90 d) for rats 50 mg/kg daily; for dogs 50 mg/kg daily.
Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks and quail >4000 mg/kg. Fish LC50 (96 h) for
bluegill sunfish and largemouth bass >1 mg/l. Bees Not toxic to bees.
azithiram
Fungicide
NOMENCLATURE:
Common name azithiram (BSI, E-ISO); azithirame ((m) F-ISO)
IUPACname bis(3,3-dimethylthiocarbazoyl) disulfide; N,N-bis(dimethylamino)thiuram
disulfide
Chemical Abstracts name 2,2,2,2-tetramethylthioperoxydicarbonic dihydrazide
([[(CH3)2NNH]C(S)]2S2) CASRN[5834946] DevelopmentcodesPP447
SmilescodeCN(C)NC(=S)SSC(=S)NN(C)C
PHYSICAL CHEMISTRY: Mol. wt. 270.5 M.f. C6H14N4S4
COMMERCIALISATION:
History Fungicide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
azobenzene
Acaricide
NOMENCLATURE:
Common name azobenzene (BSI, E-ISO, F-ISO, accepted in lieu of a common name)
IUPACname azobenzene
Chemical Abstracts name diphenyldiazene CASRN[103333]
SmilescodeN(=Nc1ccccc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 182.2 M.f. C12H10N2
COMMERCIALISATION:
History Acaricidal activity reported by W. E. Blauvelt (N.Y. State Flower Grow. Bull., 1945,
azobenzene 29
No. 2). Was mainly used in glasshouses as a smoke.

ECClassification R45; R40| Xn; R20/22 R48/22| N; R50/53
Details PM4, p. 27.
azothoate
IRAC1B
NOMENCLATURE:
Common name azothoate (BSI, E-ISO, (m) F-ISO)
IUPACname O-4-(4-chlorophenylazo)phenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-[4-[(4-chlorophenyl)azo]phenyl] O,O-dimethyl
phosphorothioate CASRN[5834968] ECno2274193
DevelopmentcodesL 1058 SmilescodeCOP(=S)(OC)Oc1ccc(N=Nc2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 356.8 M.f. C14H14ClN2O3PS
COMMERCIALISATION:
History Insecticide and acaricide introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
APPLICATIONS:
Toxicity Class WHO (a.i.) O ECClassification Xn; R20/22
azoxybenzene
NOMENCLATURE:
IUPACname azoxybenzene
Chemical Abstracts name diphenyldiazene 1-oxide Other names fenazox
CASRN[495487] ECno2078021
PHYSICAL CHEMISTRY: Mol. wt. 198.2 M.f. C12H10N2O Form Pale yellow needles.
M.p.3838.5C V.p. 13 mPa (20C) S.g./density 1.159 (20C) Solubility In water 3.4
mg/kg (25C). In ethanol 285, groundnut oil 760 g/kg (26C); in ligroin 435 g/kg (10C).
Stability Converted to o-hydroxyazobenzene by irradiation, and to p-hydroxyazobenzene
in acidic media. Stable in strongly alkaline media.
COMMERCIALISATION:
Manufacturers Fahlberg-List
30 azoxybenzene
APPLICATIONS:
ModeofactionNon-systemic, with contact action. Uses Control of mites and whitefly
on fruit trees, vines, hops, soya beans, ornamentals, vegetables and glasshouse crops.
PRODUCTS:
Discontinued products Fentoxan* (Fahlberg-List).
ANALYSIS:
Product by glc with FID. Residues by tlc, or by glc with ECD.
rabbits 1350 mg/kg. NOEL (90 d) for rats 1 mg/kg daily. Other Non-carcinogenic and
non-mutagenic. ECClassification Xn; R20/22
ECOTOXICOLOGY:
Fish LC50 (96 h) for carp 3, rainbow trout 2.7 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants Rapidly metabolised, initially to o-hydroxyazobenzene.
barban
Herbicide
NOMENCLATURE:
Common name chlorinat* (former exception, USSR); CBN (JMAF); barbanate (Republic
of South Africa); barbane ((m) F-ISO); barban (BSI, E-ISO, ANSI, WSSA)
IUPACname 4-chlorobut-2-ynyl 3-chlorocarbanilate
Chemical Abstracts name 4-chloro-2-butynyl (3-chlorophenyl)carbamate
CASRN[101279] ECno2029304 DevelopmentcodesCS-847 (Spencer
Chemicals) SmilescodeClCC#CCOC(=O)Nc1cccc(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 258.1 M.f. C11H9Cl2NO2 Form Cystalline solid;
(tech. is a tan solid).
M.p.7576C; (tech., 60C) V.p. 0.05 mPa (25C) Henry 1.17 103 Pa m3 mol1 (calc.)
S.g./density 1.403 (25C, tech.) Solubility In water 11 mg/l (25C). In benzene 327,
1,2-dichloroethane 546, hexane 1.4, kerosene 3.9, xylene 279 (all in g/l, 25C).
Stability Tech. decomposes at 224C. Stable under normal conditions of use; hydrolysis is
very rapid in alkali with displacement of the terminal chlorine substituent, DT50 58 sec (pH
13, 25C).
COMMERCIALISATION:
History Herbicide reported by A. D. Brown (Proc. North Cent.Weed Control Conf., 1958, 15,
98). Introduced by the Spencer Chemical Co. and later Velsicol Chemical Corp. Patents
US 2906614
barban 31
APPLICATIONS:
Biochemistry Acts by interfering with cell division. ModeofactionSelective herbicide,
absorbed principally by the foliage, with limited translocation in the apoplast. Uses A
selective post-em. herbicide controlling wild oats in barley at the 1.52.5 leaf stage, and
broad beans, field flax, lentils, lucerne, mustard, oilseed rape, safflower, soya beans, sugar
beet, sunflowers, wheat, Russian wild rye and other grasses.
Phytotoxicity Phytotoxic to oats and some varieties of rye. Formulation types EC.
PRODUCTS:
Discontinued products B25* (FBC); Carbyne* (Spencer Chemicals).
ANALYSIS:
Product analysis by uv spectrometry (K. J. Bombaugh & W. C. Bull, J. Agric. Food Chem., 1961,
9, 386). Residues determined by hplc or by hydrolysis to 3-chloroaniline derivatives which
are measured by glc (R. J. Harris & R. J. Whiteoak, Analyst (London), 1972, 97, 294). See also
Pestic. Anal. Man., II, 180.268. In water, by lc with uv detection (AOACMethods, 18th Ed.,
992.14).
EHC 64 (1986) is a general review of pesticides with a carbamate chemical structure. EU
Status (1107/2009) Not approved, Commission Regulation 2076/2002.
for rabbits >20000, rats >1600 mg/kg. Mildly irritating to the skin of rabbits and produces
a delayed skin sensitisation in guinea-pigs. It has been reported as a skin sensitiser in man;
skin contact should be avoided by using plastic protective clothing. Inhalation LC50 (4
h) for rats >28 mg/l air. NOEL (2 y) for rats 150 mg/kg diet, for dogs 5 mg/kg diet. In a
3-generation reproduction study in rats, NOEL 957 mg/kg diet Other Not teratogenic in
rats at 87 mg/kg daily. Non-mutagenic to mammals by in vivo and in vitro tests.
Toxicity Class WHO (a.i.) III ECClassification Xn; R22| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks and bobwhite quail >10000 mg/kg diet.
Fish LC50 (96 h) for rainbow trout 0.6, bluegill sunfish 1.2, goldfish and guppies 1.3 mg/l.
Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats and rabbits, barban is not easily absorbed through the skin. In rats,
metabolism involves hydrolysis of the carbamate group, with formation of well known
m-chloroaniline metabolites. There is no accumulation of barban or its metabolites in
tissue, and they are rapidly excreted, principally in the urine. Plants Degraded rapidly in
most plants. Metabolites include 3-chloroaniline and a glutathione conjugate.
Soil/Environment In soil, degradation involves hydrolytic cleavage of the chlorobutynyl
group, followed by decomposition of the carbamic acid so formed, with evolution of CO2,
to give 3-chloroaniline. Duration of residual activity in soil, following an application rate of
3 l/ha, is c.23 months.
32 barban
barium carbonate
Rodenticide
NOMENCLATURE:
Common name barium carbonate (JMAF) IUPACname barium carbonate (I)
Chemical Abstracts name (I) CASRN[513779] ECno2081673
Smilescode[Ba+2].[O-]C(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 197.3 M.f. CBaO3
COMMERCIALISATION:
History Used as a rodenticide for many years.
Toxicity Class WHO (a.i.) O ECClassification barium salts (with exceptions) are Xn;
R20/22 (concentration-dependent)
Details PM5, p. 28.
barium polysulfide
Fungicide, insecticide
NOMENCLATURE:
Common name barium polysulfide (E-ISO, is accepted in lieu of a common name);
polysulfure de baryum (F-ISO)
IUPACname barium polysulfide (I)
Chemical Abstracts name (I) CASRN[50864670]
PHYSICAL CHEMISTRY:
M.f. BaSx
COMMERCIALISATION:
History Insecticide and fungicide introduced by Bayer AG.
PRODUCTS:
Discontinued products Florbario* (Sariaf); Solbar* (Bayer); Tiobar* (Farmoplant).
ECClassification barium salts (with exceptions) are Xn; R20/22 (concentration-
dependent)
barium polysulfide 33
Bayer 22/190
Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O-3-chloro-4-nitrophenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(3-chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate
Other names chlorthion CASRN[500287] ECno2079025
DevelopmentcodesBayer 22/190
SmilescodeCOP(=S)(OC)Oc1ccc([N+](=O)[O-])c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 297.7 M.f. C8H9ClNO5PS M.p.21C B.p. 136C
/0.3 mbar; 112C /0.05 mbar V.p. 5.5 101 mPa (20C) Henry 4.09 103 Pa m3
mol1 (calc.) S.g./density 1.433 (420C) Solubility In water 40 mg/l (20C). Readily
soluble in common organic solvents with the exception of mineral oils. Stability Rapidly
hydrolysed in alkaline media, more slowly in the presence of acids.
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide with contact,
stomach, and respiratory action. Uses Insecticidal control of aphids and sucking and
biting insects in general in fruit, vine, and field cultivation and forestry, especially control
of the mangold fly and sawfly. Phytotoxicity Phytotoxic to a few varieties of apple (e.g.
McIntosh). Formulation types WP; DP .
PRODUCTS:
Discontinued products Chlorthion* (Bayer).
ANALYSIS:
Product by extraction with ether or petroluem ether, washing with 1% sodium carbonate
solution, reduction of the nitro group with zinc dust in glacial acetic acid/hydrochloric acid
(9:1), and titration of the amine with sodium nitrite and iodine-starch (WHO Specifications
for Pesticide, 2nd edn, Geneva, 1961). Residues: depending on the moisture content of the
sample, extraction with either acetone or chloroform, clean-up by liquid-liquid extraction
or column chromatography, and gc determination with ECD (Man. Pestic. Residue Anal.,22).
For colorimetric determination see Anal. Methods Pestic. Plant Growth Regul., 2,78, and for gc
with ECD see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 322324.
JMPR Evaln. 4 (1965).
Oral Acute oral LD50 for rats 6251500 mg/kg. Skin and eye Acute percutaneous
LD50 for rats 15004500 mg/kg. NOEL Administration of 10, 20, and 50 mg/kg diet for
34 Bayer 22/190
120 d produces no histopathological changes, apart from cholinesterase inhibition at

10 mg/kg. ADI/RfD (JMPR) No ADI [1965] ECClassification Xn; R20/21/22| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Fish Toxic to fish and animals of fish diet. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly hydrolysed to dimethyl thiophosphate and 3-chloro-4-
nitrophenol. To a limited extent, there is oxidation to the phosphate and hydrolysis to
phosphoric acid and 3-chloronitrophenol.
Bayer 22408
Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O,O-diethyl naphthalene-1,8-dicarboximido-oxyphosphonothioate;
O,O-diethyl naphthalimido-oxyphosphonothioate; N-diethoxyphosphinothioyl=
oxynaphthalene-1,8-dicarboximide
Chemical Abstracts name 2-[(diethoxyphosphinothioyl)oxy]-1H-benz[de]isoquinoline-
1,3(2H)-dione CASRN[2668920] DevelopmentcodesBayer 22408; S 125
SmilescodeCCOP(=S)(OCC)ON1C(=O)c2cccc3cccc(C1=O)c23
PHYSICAL CHEMISTRY: Mol. wt. 365.3 M.f. C16H16NO5PS
COMMERCIALISATION:
History Insecticide, discovered by W. Lorenz, evaluated by Bayer AG.
APPLICATIONS:
Bayer 32394
Fungicide
NOMENCLATURE:
IUPACname tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrate
Chemical Abstracts name tris[1-dodecyl-3-methyl-2-phenyl-1H-
benzimidazolium] hexakis(cyano-C)ferrate CASRN[7276586], formerly
[64070979] and [16071899] DevelopmentcodesBayer 32394; B 169
Ferricyanide SmilescodeCCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.
CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.CCCCCCCCCCCCn1c(c2ccccc2)
[n+](C)c3ccccc13.N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N
Bayer 32394 35
PHYSICAL CHEMISTRY: Mol. wt. 1344.7 M.f. C84H111FeN12

COMMERCIALISATION:
History Fungicide introduced by Bayer AG.
APPLICATIONS:
ModeofactionProtective fungicide.
PRODUCTS:
Discontinued products Fungilon* (Bayer).
bencarbazone
Herbicide
CH3 CF3
N
O N
N
F
NHSO2CH2CH3
C
S NH2
NOMENCLATURE:
Common name bencarbazone (BSI, E-ISO, (f) F-ISO)
IUPACname 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-
[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamide
Chemical Abstracts name 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-
triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamide
CASRN[173980171] DevelopmentcodesTM-435; HWH 4991
PHYSICAL CHEMISTRY: Mol. wt. 427.4 M.f. C13H13F4N5O3S2 Form Yellowish-grey
powder. M.p.202C
Kow logP = 0.179 (pH 7.5) Solubility In water 0.105 g/l (pH 7). Stability Hydrolysis
DT50 >500 h (pH 4), 241 h (pH 7), 174 h (pH 9) (all at 50C).
COMMERCIALISATION:
History Herbicide discovered by Bayer CropScience; licensed to Tomen Agro (later Arysta
LifeScience Corporation) in 2001.
APPLICATIONS: Uses Evaluated for post-emergence control of broad-leaved weeds in
maize and cereals.
Oral Acute oral LD50 for rats >2500 mg/kg. Skin and eye Not a skin or eye irritant. Is a
skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5045 mg/l. NOEL (13 w) for
dogs 6 mg/kg.
36 bencarbazone
ECOTOXICOLOGY:
Birds LD50 (14 d) for bobwhite quail >2000 mg/kg daily. Fish LC50 (96 h, static) for trout
>100 mg/l. Daphnia EC50 (48 h, static) >10 mg/l. Algae IC50 (72 h, static) for Selenastrum
capricornutum 2 mg/l. Worms LC50 (14 d) for earthworms >1000 mg/kg dry soil.
benclothiaz
Nematicide
Cl
S
N
NOMENCLATURE:
Common name benclothiaze ((m) F-ISO); benclothiaz (BSI, E-ISO)
IUPACname 7-chloro-1,2-benzothiazole
Chemical Abstracts name 7-chloro-1,2-benzisothiazole CASRN[89583904]
DevelopmentcodesCGA 235 860
PHYSICAL CHEMISTRY: Mol. wt. 169.6 M.f. C7H4ClNS
COMMERCIALISATION:
History Nematicide evaluated by Novartis AG.
benodanil
Fungicide
FRAC7, C2
O
C N
H
I
NOMENCLATURE:
Common name benodanil (BSI, E-ISO, (m) F-ISO) IUPACname 2-iodobenzanilide
Chemical Abstracts name 2-iodo-N-phenylbenzamide CASRN[15310017]
DevelopmentcodesBAS 3170F (BASF) SmilescodeIc1ccccc1C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 323.1 M.f. C13H10INO Form Colourless crystals.
M.p.137C V.p. <0.010 mPa (20C) Henry <1.6 104 Pa m3 mol1 (20C, calc.)
Solubility In water 20 mg/l (20C). In acetone 401, ethyl acetate 120, ethanol 93,
chloroform 77 (all in g/kg, 20C).
Stability Stable 50C; no hydrolysis (20C) at pH 1 or pH 13.
benodanil 37
COMMERCIALISATION:
History Fungicide reported by E. H. Pommer et al., at the 39th Deutsche
Pflanzenschutztagung, Stuttgart, 1973 and by F. Lcher etal. (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1974, 39, 1079). Introduced by BASF AG.
APPLICATIONS:
Biochemistry SDHI: inhibits mitochondrial function by disrupting complex II (succinate
dehydrogenase) in the respiratory electron transport chain. ModeofactionSystemic
and contact fungicide with protective and curative action. Uses Control of rust diseases of
cereals, coffee, vegetables, and ornamentals; rust and fairy rings on turf; Rhizoctonia spp. on
cotton, potatoes, cereals, rice, soya beans, ornamentals, vegetables, tobacco, and turf; and
Typhula incarnata in cereals. Formulation types WP.
PRODUCTS:
Discontinued products Calirus* (BASF).
ANALYSIS:
Product by hplc. Residues by glc with ECD.
Oral Acute oral LD50 for rats and guinea pigs >6400 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits).
NOEL (90 d) for rats >100 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Fish LC50 (96 h) for trout 6.4 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In loamy and humous sandy soils DT50 c.34 weeks.
benquinox
Fungicide
NOMENCLATURE:
Common name tserenox (USSR); benquinox (BSI, E-ISO, (m) F-ISO)
IUPACname 2-(4-hydroxyiminocyclohexa-2,5-dienylidene)benzohydrazide;
1,4-benzoquinone 1-benzoylhydrazone 4-oxime
Chemical Abstracts name benzoic acid
[4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene]hydrazide Other names COBH
CASRN[495738] ECno2078079 DevelopmentcodesBayer 15 080
SmilescodeON=C1C=CC(=NNC(=O)c2ccccc2)C=C1
PHYSICAL CHEMISTRY: Mol. wt. 241.3 M.f. C13H11N3O2 Form Yellow-brown
crystals. M.p.195C (decomp.)
38 benquinox
V.p. Non-volatile Solubility In water 5 mg/l (room temperature). Dissolves readily in

aqueous alkalis with the formation of salts. Soluble in common organic solvents, readily
soluble in formamide. Stability Very stable under normal conditions. Hydrolysed by strong
acids and alkalis.
COMMERCIALISATION:
History Fungicide reported by P. E. Frohberger (Phytopath. Z., 1956, 37, 427). Introduced by
Bayer AG.
APPLICATIONS: Uses Fungicidal dressing to protect seeds and seedlings from soil
fungi. Not used against cereal seed-borne diseases. Phytotoxicity Should not be used as a
leaf fungicide.
PRODUCTS:
Discontinued products Ceredon* (Bayer); Cereline* (Bayer);
Discontinuedmixtures Ceredon T* (+thiram) (Bayer); Rhizoctol combi*
(+methylarsenic sulfide) (Bayer); Rhizoctol slurry* (+methylarsenic sulfide) (Bayer);
Tillantox* (+phenylmercury chloride) (Bayer).
Oral Acute oral LD50 for ratsc.100 mg/kg. Toxicity Class WHO (a.i.) O
ECClassification T; R25| Xn; R21
ECOTOXICOLOGY:
Fish Toxic to fish. LC50 (48 h) for carp 0.048 mg/l. Bees Not known; irrelevant as regards
the seed dressing agent.
Details PM4, p. 35.
bentaluron
Fungicide
NOMENCLATURE:
Common name bentaluron (BSI, E-ISO, (m) F-ISO) IUPACname 1-(1,3-benzothiazol-
2-yl)-3-isopropylurea; 1-benzothiazol-2-yl-3-isopropylurea
Chemical Abstracts name N-2-benzothiazolyl-N-(1-methylethyl)urea
CASRN[28956641] DevelopmentcodesCGA 18 734
SmilescodeCC(C)NC(=O)Nc1nc2ccccc2s1
PHYSICAL CHEMISTRY: Mol. wt. 235.3 M.f. C11H13N3OS
COMMERCIALISATION:
History Fungicide evaluated by Ciba AG (later Ciba-Geigy AG).
bentaluron 39
benzadox; benzadox-ammonium
Herbicide
NOMENCLATURE:
Common name benzadox (BSI, ANSI, WSSA) IUPACname benzamido-oxyacetic acid
Chemical Abstracts name [(benzoylamino)oxy]acetic acid
CASRN[5251934] benzadox DevelopmentcodesMC 0035 (Murphy); S 6173
(Gulf) Smilescodebenzadox:OC(=O)CONC(=O)c1ccccc1
PHYSICAL CHEMISTRY: Mol. wt. 195.2; (ammonium salt 212.2) M.f. C9H9NO4;
(ammonium salt C9H12N2O4)
COMMERCIALISATION:
History Herbicidal activity reported (Farm Chem., 1967, 130, 86). Introduced by Gulf Oil
Corp. and by Murphy Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Topcide* (Gulf).
Details PM4, p. 38.
benzamacril; benzamacril-isobutyl
Fungicide
NOMENCLATURE:
Common name benzamacril (BSI, E-ISO, (m) F-ISO)
IUPACname 3-[benzyl(methyl)amino]-2-cyanoacrylic acid; 2-cyano-3-(N-
methylbenzylamino)acrylic acid
Chemical Abstracts name 2-cyano-3-[methyl(phenyl)amino]-2-propenoic acid
CASRN[88107271] benzamacril-isobutyl; [127087869] benzamacril
Smilescodebenzamacril-isobutyl:CC(C)COC(=O)C(=CN(C)Cc1ccccc1)C#N
PHYSICAL CHEMISTRY: Mol. wt. 216.2; (isobutyl ester 272.4) M.f. C12H12N2O2;
(isobutyl ester C16H20N2O2)
COMMERCIALISATION:
History Fungicide evaluated by FBC Limited (later Schering Agriculture).
benzamorf
Fungicide
NOMENCLATURE:
Common name benzamorf (BSI, E-ISO); benzamorphe ((m) F-ISO)
IUPACname morpholinium 4-dodecylbenzenesulfonate
40 benzamorf
Chemical Abstracts name 4-dodecylbenzenesulfonic acid compound with

morpholine (1:1) CASRN[12068085] DevelopmentcodesBAS 276F (BASF)
SmilescodeCCCCCCCCCCCCc1ccc(cc1)S(=O)(=O)[O-].C1COCC[NH2+]1
PHYSICAL CHEMISTRY: Mol. wt. 413.6 M.f. C22H39NO4S
COMMERCIALISATION:
History Fungicide introduced by BASF AG.
APPLICATIONS:
ModeofactionLipophilic fungicide.
benzfendizone
Herbicide
HRACE WSSA 14; pyrimidindione
CH3CH2
O O
CH3O2C O CH3
N N
CH3 O CF3
NOMENCLATURE:
Common name benzfendizone (BSI, E-ISO, (f) F-ISO)
IUPACname methyl 2-{5-ethyl-2-[4-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-
trifluoromethylpyrimidin-1-yl)phenoxymethyl]phenoxy}propionate
Chemical Abstracts name methyl 2-[2-[[4-[3,6-dihydro-3-methyl-2,6-dioxo-4-
(trifluoromethyl)-1(2H)-pyrimidinyl]phenoxy]methyl]-5-ethylphenoxy]propanoate
CASRN[158755954] DevelopmentcodesFMC 143686; F3686
SmilescodeCCc1ccc(COc2ccc(cc2)n3c(=O)cc(n(C)c3=O)C(F)(F)F)c(OC(C)C(=O)OC)c1
PHYSICAL CHEMISTRY: Mol. wt. 506.5 M.f. C25H25F3N2O6
COMMERCIALISATION:
History Herbicide evaluated by FMC.
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase. Uses Evaluated for post-
emergence control of grass and broad-leaved weeds in orchards and no-till situations; also
as a cotton defoliant and potato desiccant.
benzfendizone 41
benzipram
Herbicide
NOMENCLATURE:
Common name benzipram (BSI, E-ISO, ANSI, WSSA); benziprame ((m) F-ISO)
IUPACname N-benzyl-N-isopropyl-3,5-dimethylbenzamide
Chemical Abstracts name 3,5-dimethyl-N-(1-methylethyl)-N-(phenylmethyl)benzamide
CASRN[35256861] DevelopmentcodesS-18 510
SmilescodeCC(C)N(Cc1ccccc1)C(=O)c2cc(C)cc(C)c2
PHYSICAL CHEMISTRY: Mol. wt. 281.4 M.f. C19H23NO
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Corp.
5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone
Insecticide synergist
NOMENCLATURE:
IUPACname 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone
Chemical Abstracts name 5-(5-benzo-1,3-dioxolyl)-3-hexyl-2-cyclohexen-1-one
Other names piperonyl cyclonene CASRN[8066124]
PHYSICAL CHEMISTRY: Mol. wt. 300.4 M.f. C19H24O3
COMMERCIALISATION:
History Synergist for insecticides.
benzofluor
Herbicide
NOMENCLATURE:
Common name benzofluor (BSI, ANSI, WSSA, E-ISO, (m) F-ISO)
IUPACname 4-ethylthio-2-(trifluoromethyl)methanesulfonanilide; 4-ethylthio-,,-
trifluoromethanesulfon-o-toluidide
Chemical Abstracts name N-[4-(ethylthio)-2-(trifluoromethyl)phenyl]
methanesulfonamide CASRN[68672173] DevelopmentcodesMBR 18 337
SmilescodeCCSc1ccc(NS(=O)(=O)C)c(c1)C(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 299.3 M.f. C10H12F3NO2S2
COMMERCIALISATION:
History Herbicide and plant growth regulator introduced by 3M Company.
42 benzofluor
benzoylprop; benzoylprop-ethyl
Herbicide
NOMENCLATURE:
Common name benzoylprop (BSI, E-ISO, (m) F-ISO, WSSA)
IUPACname N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine (I)
Chemical Abstracts name (I) CASRN[22212551] benzoylprop-ethyl; [2221256
2] benzoylprop ECno2448455 benzoylprop-ethyl DevelopmentcodesWL 17 731
(ester)
PHYSICAL CHEMISTRY:
Composition Tech. is 93%. Mol. wt. 338.2; (ethyl ester 366.2) M.f. C16H13Cl2NO3; ethyl
ester C18H17Cl2NO3
Form Tech. benzoylprop-ethyl is an off-white crystalline powder. M.p.7071C (ester)
V.p. 0.0047 mPa (20C, ester) Solubility In water c.20 mg/l (25C, ester). In acetone
700750, Shellsol A 250300 (both g/l, 25C, for ester). Stability Stable photochemically,
and hydrolytically over at least the range pH 3 to pH 6.
COMMERCIALISATION:
History Benzoylprop-ethyl is a herbicide reported by T. Chapman etal. (Symp. New. Herbic.,
3rd, 1969, p. 40). Introduced by Shell Research Ltd. Patents GB 1164160
APPLICATIONS:
ModeofactionSelective herbicide Uses Applied at 1.01.5 kg/ha to wheat, it gives an
8595% control of wild oat (Avena barbata, A. fatua, A. ludoviciana, A. sterilis). Field beans,
oilseed rape and culinary mustard may also be safely treated. Crop competition ensures
the effective control of wild oat, the stem elongation of which is inhibited (B. Jeffcoat & W.
N. Harries, Pestic. Sci., 1973, 4, 891). Formulation types EC.
PRODUCTS:
Discontinued products Suffix* (Shell).
ANALYSIS:
Product analysis (ester) by glc (CIPACHandbook, 1983, 1B, 1732) or by i.r. spectroscopy.
Residues determined by glc with ECD (A. N. Wright & B. L. Mathews, Pestic. Sci., 1976, 7, 339).
Oral Acute oral LD50 for rats 1555, for mice 716 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >1000 mg/kg. NOEL In 90 d feeding trials, no change of
toxicological significance in rats receiving 1000 mg/kg diet or dogs 300 mg/kg diet.
Toxicity Class WHO (a.i.) III (for ethyl ester) ECClassification Xn; R22| N; R50, R53
(for DL-benzoylprop-ethyl)
ENVIRONMENTAL FATE:
The fate of the compound in plants, soils and animals has been reported (K. I. Beynon et al.,
benzoylprop; benzoylprop-ethyl 43
Pestic. Sci., 1974, 5, 429, 443, 451; J.V. Crayford et al., ibid., 1976, 7, 559).
benzthiazuron
Herbicide
S
NHCONHCH3
N
NOMENCLATURE:
Common name benzthiazuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(1,3-benzothiazol-2-yl)-3-methylurea; 1-benzothiazol-2-yl-3-methylurea
Chemical Abstracts name N-2-benzothiazolyl-N-methylurea CASRN[1929880]
ECno2176859 DevelopmentcodesBayer 60 618
SmilescodeCNC(=O)Nc1nc2ccccc2s1
PHYSICAL CHEMISTRY: Mol. wt. 207.3 M.f. C9H9N3OS Form Colourless powder.
M.p.Decomposes (without melting) at 305-313C V.p. 1.3 mPa (92C, extrapolated)
Solubility In water 15 mg/l (20C). In organic solvents such as acetone, chlorobenzene,
DMF, xylene, isobutanol
510 mg/l; dichloromethane 3, toluene 1, isopropanol 4 (all in g/l, 20C).
Stability Hydrolysed by strong acids and alkalis.
COMMERCIALISATION:
History Herbicide reported by H. Hack (International Meeting on Selective Weed Control
in Sugar Beet Crops, Marly-le-Roi, 910 March 1967). Introduced in the Netherlands
(1967) by Bayer AG. Patents BE 647740; GB 1004469
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II
receptor site. Interferes with cellular division at the level of RNA biosynthesis, and inhibits
photosynthesis. ModeofactionSelective herbicide, absorbed mainly by the roots. Uses
Pre-emergence control of many germinating annual broad-leaved weeds in sugar beet,
fodder beet, and spinach at 3.26.4 kg/ha. Formulation types WP. Compatibility
Incompatible with quintozene and disulfoton.
PRODUCTS:
Discontinued products Gatnon* (Bayer).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by uv spectroscopy (H. J. Jarczyk
& K.Vogeler, Pflanz.-Nachr. Bayer (Engl. Ed.), 1967, 20, 575).
44 benzthiazuron
Oral Acute oral LD50 for male rats >2500, male mice >1000, male dogs >1000 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >500 mg/kg. Irritating to eyes; non-
irritating to skin. NOEL (90 d) for rats 1000 mg/kg. In 60 d feeding trials, rats receiving
130 mg/kg daily showed no ill-effects. Toxicity Class WHO (a.i.) III
ECClassification Xn; R22
ECOTOXICOLOGY:
Fish Non-toxic to fish.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 c.1012 weeks.
bethoxazin
Algicide, fungicide
S N
O
S
O
NOMENCLATURE:
Common name bethoxazine ((f) F-ISO); bethoxazin (BSI, E-ISO (not Japan))
IUPACname 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine 4-oxide
Chemical Abstracts name 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine
4-oxide CASRN[163269305] ECno4310306 DevelopmentcodesR 102622
SmilescodeO=S1C(C2=CC3=CC=CC=C3S2)=NOCC1
PHYSICAL CHEMISTRY: Mol. wt. 251.3 M.f. C11H9NO2S2
COMMERCIALISATION:
Manufacturers Janssen
binapacryl
Acaricide, fungicide
FRAC29, C5; dinitrophenyl crotonate
NOMENCLATURE:
Common name binapacryl (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF)
IUPACname 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenyl 3-methyl-2-
butenoate CASRN[485314] ECno2076129 DevelopmentcodesHoe 02 784
SmilescodeCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)C=C(C)C)[N+](=O)[O-]
binapacryl 45
PHYSICAL CHEMISTRY:
Composition Tech. is 97%. Mol. wt. 322.3 M.f. C15H18N2O6 Form Colourless
crystalline powder. M.p.6667C; (tech., 6569C) V.p. 13 mPa (60C) S.g./density
1.2 (20C); (tech. 1.251.28 (20C)) Solubility In water c.1 mg/l (pH 5, 20C). In
hexanec.0.4, dichloromethane, ethyl acetate, toluene >500, methanolc.21 (all in g/l, 20C).
Stability Slowly decomposed by uv light; unstable in alkali and concentrated acids, and
suffers slight hydrolysis on long contact with water.
COMMERCIALISATION:
History Acaricide and fungicide reported by L. Emmel & M. Czech (Anz. Schaedlingskd.,
1960, 33, 145). Introduced by Hoechst AG. Patents GB 855736; DE 1099787
APPLICATIONS:
Biochemistry Uncouples mitochondrial oxidative phosphorylation.
ModeofactionNon-systemic acaricide with contact action. Also a contact fungicide
which acts by preventing germination of the conidia, and thus blocking reinfection.
Uses Effective against powdery mildews; used mainly against all stages of spider mites
and powdery mildews of apples, citrus, cotton, pears and top fruit at 2550 g/100 l.
Phytotoxicity Phytotoxic to blackcurrants, cyclamens, and to hydrangeas under glass.
Formulation types EC; WP; SC. Compatibility Incompatible with alkalis. May be
phytotoxic when mixed with some organophosphorus compounds.
PRODUCTS:
Discontinued products Acricid* (Hoechst); Endosan* (Hoechst); Morocide*
(Hoechst); Morrocid* (Hoechst).
ANALYSIS:
Product analysis by hydrolysis to the parent phenol (dinoseb, q.v.) measured by colorimetry
(D. S. Farrington et al., Analyst (London), 1983, 108, 353) or by titration with titanium
trichloride. Residues determined by the former method (Pestic. Anal. Manual, 1979, I, 201-A,
201G; P. B. Baker & R. A. Hoodless, Analyst (London), 1973, 98, 172; R. W. Buxton &
T. A. Mohr, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 235; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 314).
JMPR Evaln. II 46 (1985). ICSC.835 (1997). EU Status (1107/2009) Considered to be
outside the scope of the Directive; already banned, 79/117/EEC as amended by 90/533/EEC.
Oral Acute oral LD50 for rats 150225, male mice 16003200, female guinea pigs 300, dogs
450640 mg/kg. Skin and eye Acute percutaneous LD50 (acetone solution) for rabbits and
mice 750 mg/kg. Slight eye irritant.
NOEL In 2 y feeding trials, rats receiving 500 mg/kg diet and dogs receiving 50 mg/kg diet
showed no ill-effects. ADI/RfD (JMPR) No ADI [1985]. Toxicity Class WHO (a.i.) II
ECClassification R61| Xn; R21/22| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens 800 mg/kg. Fish Max. tolerated dose for guppies 0.5,
46 binapacryl
carp 1.0, trout 2.0 mg/l. Bees Not toxic to bees.

ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, hydrolysed to dinoseb (q.v.).
Soil/Environment Duration of activity in soil is 1525 d.
biopermethrin
Insecticide
IRAC3 A single isomer, component of permethrin.
O
CH2 O
H C O
Cl
C CH H
CH3 CH3
Cl
NOMENCLATURE:
Common name bioperm(thrine) ((f) F-ISO); biopermethrin (BSI, E-ISO)
IUPACname 3-phenoxybenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethy
lcyclopropanecarboxylate; 3-phenoxybenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-
dimethylcyclopropanecarboxylate
Chemical Abstracts name (1R-trans)-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-
2,2-dimethylcyclopropanecarboxylate; (3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate Other names permethrin-B;
1R-trans-permethrin CASRN[51877748] DevelopmentcodesNRDC 147; RU
22090 SmilescodeCC1(C)C(C=C(Cl)Cl)C1C(=O)OCc2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY: Mol. wt. 391.3 M.f. C21H20Cl2O3
APPLICATIONS:
Biochemistry Acts on the nervous system of insects, and disturbs the function of
neurons by interaction with the sodium channel.
ANALYSIS:
Analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Anal. Profiles.
Permethrin isomers in drinking water by glc with ECD (AOACMethods, 18th Ed., 990.06).
See A. J. Gray & D. M. Soderlund, Chapt. 5 in Insecticides.
biopermethrin 47
biphenyl
Fungicide
FRAC14, F3; aromatic hydrocarbon

NOMENCLATURE:
Common name biphenyl (BSI, E-ISO, F-ISO, accepted in lieu of common name)
IUPACname biphenyl
Chemical Abstracts name 1,1-biphenyl Other names diphenyl CASRN[92524]
ECno2021635 Smilescodec1ccc(cc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 154.2 M.f. C12H10 Form Colourless crystals.
M.p.70.5C B.p. 256C V.p. 4 Pa (20C) (CICAD) Kow logP = 3.884.04 (CICAD) S.g./
density 1.041 Solubility In water 4.45 mg/l (20C) (CICAD). Readily soluble in ethanol,
diethyl ether, and other organic solvents. Stability Very stable in acidic and alkaline media.
F.p. 106C
COMMERCIALISATION:
History Fungicidal activity against citrus-rotting fungi described by G. B. Ramsey etal. (Bot.
Gaz., 1944, 106, 74).
APPLICATIONS:
Biochemistry Proposed mode of action is lipid peroxidation. ModeofactionFungistat
which inhibits sporulation. Uses Used to impregnate citrus fruit wraps to prevent fungal
attack. Formulation types Impregnated material.
ANALYSIS:
Residues determined by uv spectrometry (F. A. Gunther et al., Analyst (London), 1963, 88, 36;
F. A. Gunther & D. E. Ott, ibid., 1966, 91, 475; S. Norman et al., J. Assoc. Off. Anal. Chem., 1966,
49, 590; AOACMethods, 18th Ed., 968.25), by glc (H. Pyysalo et al., J. Chromatogr., 1979, 168,
512; Man. Pestic. Residue Anal., p. 6) or by hplc (J. E. Farrow et al., Analyst (London), 1977, 102,
752). See also Pestic. Anal. Man., I, 302.
JMPR Evaln. 7 (1966), 9 (1967). ICSC.106 (1994). CICAD 6 (1999).
Oral Acute oral LD50 for rats 3280, rabbits 2400, cats >2600 mg/kg. Depression of the
central nervous system, paralysis, and convulsions have been observed in experimental
animals. Inhalation Prolonged exposure of humans to vapour concentrations >0.005 mg/l
air is considered dangerous (J. Deichmann et al., J. Ind. Hyg.Toxicol., 1947, 29, 1).
NOEL NOAEL for rats 50 mg/kg b.w. daily (EPA IRIS).
48 biphenyl
ADI/RfD (JMPR) 0.125 mg/kg b.w. [1967]; (EPA) cRfD 0.05 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) U EPA (formulation) III ECClassification Xi; R36/37/38| N;
R50, R53
ECOTOXICOLOGY:
Fish LC50 (96 h) for fish 1.54.7 mg/l, with rainbow trout and fathead minnow the most
sensitive species (CICAD). Daphnia LC50 (8 h) 0.36 mg/l.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolites identified include
4-hydroxybiphenyl and other phenolic compounds (H. D. West et al., Arch. Biochem. Biophys.,
1956, 60, 1420). Plants Residues in fruit have been reviewed (A. Rajzman, Residue Rev.,
1964, 8, 1; S. W. Souci & G. Maier-Haarlnder, ibid., 1966, 16, 103).
bis(2-chloroethyl) ether
Insecticide
NOMENCLATURE:
Common name dichloroethyl ether (ESA)
IUPACname bis(2-chloroethyl) ether; di-(2-chloroethyl) ether
Chemical Abstracts name 1,1-oxybis[2-chloroethane] Other names DCEE
CASRN[111444] ECno2038701 SmilescodeClCCOCCCl
PHYSICAL CHEMISTRY: Mol. wt. 143.0 M.f. C4H8Cl2O
COMMERCIALISATION:
History Insecticidal activity reported by R. C. Roark & R. T. Cotton (USDA Tech. Bull., 1929,
No. 162); used to fumigate soil.
APPLICATIONS:
ModeofactionFumigant insecticide.
PRODUCTS:
Discontinued products Chlorex* (Union Carbide).
EHC 201 (1998). ICSC.417 (2000). IARC 9 (1975); 71 (1999).
IARC Class 3 ECClassification R40| T+; R26/27/28; concn. dep.
bis(2-chloroethyl) ether 49
1,1-bis(4-chlorophenyl)-2-ethoxyethanol
Acaricide
NOMENCLATURE:
IUPACname 1,1-bis(4-chlorophenyl)-2-ethoxyethanol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--(ethoxymethyl)
benzenemethanol CASRN[6012835] DevelopmentcodesGeigy 337; G 23 645
SmilescodeCCOCC(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
COMMERCIALISATION:
History Acaricide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinued products Etoxinol* (Ciba-Geigy).
Oral Acute oral LD50 for rats >5000 mg/kg (Shibuya).
bis(methylmercury) sulfate
Fungicide
NOMENCLATURE:
IUPACname bis(methylmercury) sulfate
Chemical Abstracts name dimethyl--sulfatodimercury CASRN[3810819]
SmilescodeC[Hg]OS(=O)(=O)O[Hg]C
PHYSICAL CHEMISTRY: Mol. wt. 527.3 M.f. C2H6Hg2O4S
COMMERCIALISATION:
PRODUCTS:
Discontinued products Aretannieuw* (Bayer); Cerewet* (Bayer).
JMPR Evaln. 9 (1967) EU Status (1107/2009) Alkyl mercury compounds considered to
be outside the scope of the Directive; already banned, 79/117/EEC.
IARC Class methylmercury compounds are classified 2B
ECClassification Not specified, but organic mercury generally is assigned T+; R26/27/28|
R33| N; R50, R53, concentration-dependent. PIC Not specifically listed in the relevant
DGD, but all mercury compounds are included in the PIC procedure.
Details PM2, p. 47.
50 bis(methylmercury) sulfate
bisthiosemi
Rodenticide
NOMENCLATURE:
Common name bisthiosemi (JMAF)
IUPACname 1,1-methylenedi(thiosemicarbazide)
Chemical Abstracts name 2,2-methylenebis(hydrazinecarbothioamide)
CASRN[39603480] DevelopmentcodesNK-15 561
SmilescodeNC(=S)NNCNNC(=S)N
PHYSICAL CHEMISTRY: Mol. wt. 194.3 M.f. C3H10N6S2 Form Colourless crystals.
M.p.Decomposes at
171174C Solubility Almost insoluble in water and common organic solvents. Soluble
in DMSO. Stability Decomposes slowly in water, and more rapidly in acidic or alkaline
conditions.
COMMERCIALISATION:
History Rodenticide introduced by Nippon Kayaku Co., Ltd. Patents JP 50020126; GB
1351710; US 3826841
APPLICATIONS: Uses Control of Rattus norvegicus, Rattus rattus, and Microtus montebelli.
Formulation types RB .
PRODUCTS:
Discontinued products Kayanex* (Nippon Kayaku).
ANALYSIS:
Product analysis by hydrolysis to thiosemicarbazide which is measured colorimetrically as a
derivative.
Oral Acute oral LD50 for mice 30.450, guinea pigs 3236, catsc.150, dogs >1500 mg/kg.
NOEL (90 d) for mice 100 mg/kg diet; for rats 50 mg/kg diet.
Toxicity Class WHO (a.i.) II
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens 120150 mg/kg.
bisthiosemi 51
bis(tributyltin) oxide
Fungicide
CH3(CH2)3 (CH2)3CH3
CH3(CH2)3 Sn O Sn (CH2)3CH3
CH3(CH2)3 (CH2)3CH3
NOMENCLATURE:
IUPACname bis(tributyltin) oxide
Chemical Abstracts name hexabutyldistannoxane CASRN[56359]
SmilescodeCCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
PHYSICAL CHEMISTRY: Mol. wt. 596.1 M.f. C24H54OSn2 Form Colourless to pale
yellow oil. M.p.45C
B.p. 180C /2 mmHg V.p. Negligible (20C) S.g./density 1.14 Solubility In water
c.100 mg/l; in sea water 60 mg/l (room temperature). Miscible with most organic solvents.
Stability Stable to storage in dark, closed containers; forms bis(tributyltin) carbonate on
exposure to air.
COMMERCIALISATION:
History Fungicide reported by J. G. A. Luijten & G. J. M. van der Kerk, Investigations
Organotin. Introduced (1966) by M & T Chemicals Ltd.
APPLICATIONS: Uses Mainly used as a toxicant in marine antifouling paints, to control
Algae in industrial cooling water and as a wood preservative. Phytotoxic and unsuitable
for use on growing crops or on cultivated soil.
ANALYSIS:
Product analysis by wet oxidation, reduction to tin(II) measured by titration with potassium
iodate. Residues determined by hydrolysis to tin(II) salts estimated by colorimetry with
dithiol (R. E. D. Clark, Analyst (London), 1936, 61, 242; 1937, 62, 661).
EHC 116 (1990); a general review of tributyl tin compounds. PDS 65 (1985). ICSC.282
(1998). CICAD 14 (1999). EU Status (1107/2009) Not approved, as tributyltinoxyde,
Commission Regulation 2076/2002.
Oral Acute oral LD50 for rats 194 mg a.i. (as aqueous suspension)/kg (J. Elsea & O. E.
Paynter, AMA Arch. Ind. Health, 1958, 18, 214). Skin and eye Absorbed by skin and may
cause irritation. NOEL BMD10 (18 mo) immunotoxicity for rats 0.03 mg/kg b.w. daily (J. G.
Vos, et al., 1990. Toxicol. Appl. Pharmacol. (1990) 105, 144155, cited by EPA).
ADI/RfD (EPA) cRfD 0.003 mg/kg b.w. [1997]. Water GV Excluded from GV derivation
(U). Toxicity Class WHO (a.i.) Ib
52 bis(tributyltin) oxide
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt

Fungicide
NH2
N
HO2C
N O
O
CH3 NH2
H2NC N CH2CH2 C CH2CO NH
NH H
blasticidin S
NH
CH2
SO3H
benzylaminobenzenesulfonic acid
See also The Manual of Biocontrol Agents entry: 2:160
FRAC23, D2; enopyranuronic acid antibiotic
NOMENCLATURE:
Common name blasticidin-S (JMAF)
IUPACname 1-(4-amino-1,2-dihydro-2-oxopyrimidin-1-yl)-4-[(S)-3-amino-5-(1-
methylguanidino)valeramido]-1,2,3,4-tetradeoxy--d-erythro-hex-2-enopyranuronic acid
Chemical Abstracts name (S)-4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-
oxopentyl]amino]-1-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,2,3,4-tetradeoxy--d-erythro-
hex-2-enopyranuronic acid (blasticidin); 4-[(phenylmethyl)amino]benzenesulfonic acid,
compound with (S)-4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]
amino]-1-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,2,3,4-tetradeoxy--d-erythro-hex-2-
enopyranuronic acid (BABS salt) Other names Bla-S
CASRN[2079007] blasticidin, formerly [11002929] and [12767554];
[51775281] BABS salt DevelopmentcodesBcS-3
SmilescodeCN(CC[C@@H](N)CC(=O)N[C@H]1/C=C\[C@H](OC1C(=O)
O)n2ccc(N)nc2=O)C(=N)N; without stereochemistry:CN(CCC(N)CC(=O)
NC1C=CC(OC1C(=O)O)n2ccc(N)nc2=O)C(=N)N; BABS salt, without
stereochemistry:CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](OC1C(=O)O)
n2ccc(N)nc2=O)C(=N)N.OS(=O)(=O)c1ccc(NCc2ccccc2)cc1
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt 53

PHYSICAL CHEMISTRY: Mol. wt. 422.4; 685.6 (BABS salt) M.f. C17H26N8O5; BABS
salt C30H39N9O8S
Form Colourless needles; (tech., light brown solid). M.p.235-236C (decomp.)
Solubility In water >30 g/l (20C). In acetic acid >30 g/l (20C). Practically insoluble in
acetone, benzene, carbon tetrachloride, chloroform, cyclohexane, dioxane, ethanol, diethyl
ether, ethyl acetate, methanol, pyridine, xylene. Stability Stable at pH 57; unstable at pH
<4 and in alkali. Stable to light. Specific rotation []11D +108.4 (c = 1.0 in water)
pKa pKa1 2.4 (carboxyl), pKa2 4.6, pKa3 8.0, pKa4 >12.5 (three bases)
COMMERCIALISATION:
Production By the fermentation of Streptomyces griseochromogenes. History Antibiotic
discovered by K. Fukunaga etal. (Bull. Agric. Chem. Soc. Jpn, 1955, 19, 18), its fungicidal
properties reported by T. Misato etal. (Nippon Shokubutsu Byori Gakkaiho, 1959, 24,
302) and its structure elucidated by N. Otake (Agric. Biol. Chem., 1967, 30, 132). Its
benzylaminobenzenesulfonate salt was introduced by Kaken Chemical Co., Ltd (later Kaken
Pharmaceutical Co. Ltd), Kumiai Chemical Industry Co., Ltd, and Nihon Nohyaku Co., Ltd.
APPLICATIONS:
Biochemistry Protein synthesis inhibitor. ModeofactionContact fungicide with
protective and curative action. Uses The BABS salt was used for control of rice blast
(Pyricularia oryzae), by foliar application at 1040 g/ha. Phytotoxicity Damage can
be caused to alfalfa, aubergines, clover, potatoes, soya beans, tobacco, and tomatoes.
Excessive application produces yellow spots on rice leaves. Formulated as the
benzylaminobenzenesulfonate salt, to reduce phytotoxicity. Formulation types DP; EC;
WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Bla-S* (BABS salt) (Nihon Nohyaku).
ANALYSIS:
Product analysis by bioassay with Bacillus cereus IAM-1729. Residues determined by
bioassay with Fulvia fulva ACI-1164.
Oral Acute oral LD50 for male rats 56.8, female rats 55.9, male mice 51.9, female
mice 60.1 mg/kg. BABS salt, acute oral LD50 for rats 53.3 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >500 mg/kg. Severe eye irritant. NOEL (2 y) for rats 1 mg/kg
diet. Other Non-mutagenic in bacterial reversion tests. Toxicity Class WHO (a.i.) Ib EPA
(formulation) II ECClassification T+; R28
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp >40 mg/l. Daphnia LC50 (3 h) for D. pulex >40 mg/l.
ENVIRONMENTAL FATE:
Animals Almost all of 3H-blasticidin-S administered to mice was excreted in the urine and
faeces within 24 h. Plants In rice plants, cytomycin and deaminohydroxy blasticidin-S were
identified as the main metabolites. Soil/Environment In soil, DT50 <2 d (two soil types,
o.c. 2.53%, 9.6%; moisture 42.6%, 87%, respectively; pH 6.0, 25C).
54
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt
bromfenvinfos
Insecticide
IRAC1B
NOMENCLATURE:
Common name bromfenvinfos (BSI, E-ISO, (m) F-ISO)
IUPACname 2-bromo-1-(2,4-dichlorophenyl)vinyl diethyl phosphate [(E)- to (Z)- ratio
c.1:18]
Chemical Abstracts name 2-bromo-1-(2,4-dichlorophenyl)ethenyl diethyl phosphate
CASRN[33399007] unstated stereochemistry; [58580146] (E)- isomer; [5858013
5] (Z)- isomer DevelopmentcodesIPO-62
SmilescodeCCOP(=O)(OCC)OC(=CBr)c1ccc(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 404.0 M.f. C12H14BrCl2O4P
COMMERCIALISATION:
History Insecticide.
APPLICATIONS:
3-bromo-1-chloroprop-1-ene
Insecticide
NOMENCLATURE:
IUPACname 3-bromo-1-chloroprop-1-ene
Chemical Abstracts name 3-bromo-1-chloro-1-propene CASRN[3737006]
DevelopmentcodesCBP-55 SmilescodeCC(=CCl)Br
PHYSICAL CHEMISTRY: Mol. wt. 155.4 M.f. C3H4BrCl
COMMERCIALISATION:
History Fumigant insecticide for soil introduced by Shell Development Co.
APPLICATIONS: Uses Soil-fumigant insecticide
1-bromo-2-chloroethane
Insecticide
NOMENCLATURE:
IUPACname 1-bromo-2-chloroethane (I)
Chemical Abstracts name (I) Other names ethylene chlorobromide; sym-
chlorobromoethane CASRN[107040] SmilescodeClCCBr
PHYSICAL CHEMISTRY: Mol. wt. 143.4 M.f. C2H4BrCl
1-bromo-2-chloroethane 55
COMMERCIALISATION:
History Insecticide used to fumigate soil, reported by M. W. Stone & F. B. Foley (J. Econ.
Entomol., 1951, 44, 711).
APPLICATIONS: Uses Soil-fumigant insecticide.
bromobonil
Herbicide
NOMENCLATURE:
Common name bromobonil (BSI, E-ISO, (m) F-ISO)
IUPACname 2,6-dibromo-4-cyanophenyl tetrahydrofurfuryl carbonate
Chemical Abstracts name 2,6-dibromo-4-cyanophenyl (tetrahydro-2-furanyl)methyl
carbonate CASRN[25671469] unstated stereochemistry
SmilescodeBrc1cc(C#N)cc(Br)c1OC(=O)OCC2CCCO2
PHYSICAL CHEMISTRY: Mol. wt. 405.1 M.f. C13H11Br2NO4
COMMERCIALISATION:
History Herbicide evaluated by Boehringer & Sohn (became Shell Agrar).
bromocyclen
Acaricide, insecticide, ixodicide
NOMENCLATURE:
Common name bromocyclen (BSI, E-ISO, BPC); bromocycl(ne) ((m) F-ISO)
IUPACname 5-bromomethyl-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene;
5-bromomethyl-1,2,3,4,7,7-hexachloro-8,9,10-trinorborn-2-ene
Chemical Abstracts name 5-(bromomethyl)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-
2-ene CASRN[1715408] SmilescodeClC1=C(Cl)C2(Cl)C(CBr)CC1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. isc.90%. Mol. wt. 393.8 M.f. C8H5BrCl6
COMMERCIALISATION:
History Veterinary insecticide and acaricide introduced by Hoechst AG.
APPLICATIONS: Uses An insecticide and acaricide effective against ectoparasites such
as Chorioptes, Cnemidocoptes, Notoedres, Otodectes, Psoroptes, Sarcoptes spp. and Cheyletiella
parasitivorax on cats, cattle, dogs, horses, pigs, sheep and some birds. The host may be
dusted, bathed or treated with an aerosol of bromocyclen. Formulation types AE; DP;
WP.
PRODUCTS:
Discontinued products Aludan* (Hoechst); Alugan* (Hoechst); Bromodan* (Hoechst).
56 bromocyclen

Oral Acute oral LD50 for rats 12500 mg/kg. Toxicity Class WHO (a.i.) U
bromofenoxim
Herbicide
HRACC3 WSSA 6
Br NO2
HO CH N O NO2
Br
NOMENCLATURE:
Common name bromofenoxim (BSI, E-ISO, WSSA); bromoph(noxime) ((f) F-ISO)
IUPACname 3,5-dibromo-4-hydroxybenzaldehyde 2,4-dinitrophenyloxime
Chemical Abstracts name 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)
oxime CASRN[13181174], formerly [37273851] ECno2361296
DevelopmentcodesC 9122
SmilescodeOc1c(Br)cc(C=NOc2ccc(cc2[N+](=O)[O-])[N+](=O)[O-])cc1Br
PHYSICAL CHEMISTRY: Mol. wt. 461.0 M.f. C13H7Br2N3O6 Form Cream-coloured
crystals. M.p.196197C
V.p. <1 105 mPa (20C) Kow logP = 3.17 (pH 7.0) Henry 7.68 106 Pa m3 mol1
(pH 3.8, 20C, calc.) S.g./density 2.15 (20C) Solubility In water 0.6 (pH 3.8), 9.0
(pH 10) (both in mg/l, 20C). In hexane 200, isopropanol 400, acetone 9900, n-octanol 200
(all in mg/l, 20C). Stability On hydrolysis, DT50 (70C) 41.4 h (pH 1), 9.6 h (pH 5),
0.76 h (pH 9). pKa 5.46, weak acid
COMMERCIALISATION:
History Herbicide reported by D. H. Green etal. (Symp. New Herbic., 3rd, 1969, p. 77).
Introduced by Ciba AG (later Novartis Crop Protection AG). Patents BE 675444; GB
1096037 Manufacturers Novartis
APPLICATIONS:
Biochemistry Generates bromoxynil (q.v.). ModeofactionSelective herbicide with
contact action. Absorbed by the leaves and stems, with some translocation. Uses Post-
emergence control of many annual broad-leaved weeds in cereals, maize, grass-seed crops,
grassland, and newly-seeded turf at rates in the range 1.02.5 kg/ha. Used in combination
with other herbicides to extend the spectrum and period of activity. Formulation types
WP; SC.
bromofenoxim 57
PRODUCTS:
Discontinued products Dicoprime* (Ciba-Geigy); Faneron* (Novartis).
ANALYSIS:
Product analysis by hplc. Residues determined by hplc.
Oral Acute oral LD50 for rats 1217, dogs >1000, mice 940 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >3000 mg/kg. Mild skin and eye irritant (rabbits).
Inhalation LC50 (6 h) for rats >0.242 mg/l air. NOEL (2 y) for rats 100 mg/kg diet
(3.8 mg/kg b.w. daily); (3 mo) for dogs 100 mg/kg diet (3 mg/kg b.w. daily), for mice
10 mg/kg diet (0.63 mg/kg b.w.. daily). ADI/RfD (BfR) 0.0015 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification Xn; R22| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for Japanese quail 5560, bobwhite quail 4000, mallard ducklings
2800 ppm. Fish LC50 (96 h) for rainbow trout 0.18, carp 0.088 mg/l. Daphnia LC50 (48 h)
1.2 mg/l. Algae EC50 (96 h) for Algae 2.2 mg/l. Bees WP non-toxic; SC toxic.
Worms LC50 (14 d) for earthworms c.1300 mg/kg. Other beneficial No effect on soil
respiration, ammonification or nitrification.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, dinitrophenol and
hydroxydibromobenzonitrile are formed, and are more slowly metabolised further and
excreted in the urine; unchanged parent is the primary excretion product in the faeces.
Plants In plants, 3,5-dibromo-4-hydroxybenzoic acid has been identified as a metabolite.
There is some conversion to bromoxynil. Soil/Environment Of low mobility with little
or no persistence in the soil; DT50 0.55 d. Koc 1100.
bromophos
Insecticide
Cl
S OCH3
Br O P
OCH3
Cl
IRAC1B
NOMENCLATURE:
Common name bromophos (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname O-4-bromo-2,5-dichlorophenyl O,O-dimethyl phosphorothioate
58 bromophos
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl) O,O-

dimethyl phosphorothioate CASRN[2104963] ECno2182773
DevelopmentcodesS-1942 SmilescodeCOP(=S)(OC)Oc1cc(Cl)c(Br)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 366.0 M.f. C8H8BrCl2O3PS Form Yellow crystals.
M.p.5354C
B.p. 140142C /0.01 mmHg V.p. 17 mPa (20C) Henry 8.89 Pa m3 mol1 (20C, calc.)
Solubility In water 0.7 (20C), 40 (25C) (both in mg/l). In acetone 1090,
dichloromethane 1120, xylene 900, methanol 100 (all in g/l, 20C). Stability Stable in
solution up to pH 9 and in aqueous suspension, but hydrolysed in alkaline media.
COMMERCIALISATION:
History Insecticide reported by R. Immel & G. Geisthardt (Meded. Landbouwhogesch.
Opzoekingsstn. Staat Gent, 1964, 29, 1242), and reviewed by D. Eichler (Residue Rev., 1972, 41,
65). Introduced by C. H. Boehringer Sohn/Cela GmbH (later Shell Agrar GmbH). Patents
DE 1174104; GB 956343
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic insecticide with
contact and stomach action. Uses Control of Diptera, Hemiptera, some Lepidoptera,
Coleoptera, and other insects in fruit, vegetables, field crops, ornamentals, and forestry.
Important uses included control of cabbage root flies, carrot flies, onion flies, beet leaf
miners, wheat bulb flies, frit flies, and bean seed flies. Also used for control of stored-
product insect pests; in public health for control of flies, mosquitoes, etc.; as a household
insecticide; for control of insects in animal houses; and as an animal dip.
Phytotoxicity Phytotoxic to cotton and vines. Some varieties of pear, cabbage, and
ornamentals, and glasshouse crops may be injured. Formulation types AE; DP; EC; WP;
GR; KN; Seed treatment. Compatibility Not compatible with sulfur, organometallic
compounds and alkaline pesticides.
PRODUCTS:
Discontinued products Farel* (Shell); Nexion* (Shell).
ANALYSIS:
Product by oxidation with bromide-bromate solution, and titration of the excess bromate
with sodium thiosulfate (CIPACHandbook, 1983, 1B, 1738; R. D. Weeren and D. Eichler Anal.
Methods Pestic. Plant Growth Regul. 1978, 10, 3334). Residues by glc with phosphorus-
specific FID (R. D. Weeren Anal. Methods Pestic. Plant Growth Regul. 1978, 10, 3540;
M. A. Luke et al., J. Assoc. Off. Anal. Chem. 1981, 64, 1187. Analyst (London), 1980, 105, 515); by
fluorogenic labelling with dansyl chloride and tlc (S. Traore & J. J. Aaron Talanta 1981, 28(10),
765767). See also Pestic. Anal. Man., I, 503. Determination of the halogenated phenol
produced by hydrolysis can be used for both product and residue analysis.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. I 45
(1985); JMPR Evaln. 43 (1984). PDS 76 (1994). EU Status (1107/2009) Not approved,
bromophos 59
Oral Acute oral LD50 for rats 37508000, mice 33115850, rabbits 720, guinea pigs
1500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 2188 mg/kg. NOEL (2 y)
for rats 0.63 mg/kg daily, for dogs 1.5 mg/kg daily. ADI/RfD (JMPR) 0.04 mg/kg b.w. [1977].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification Xn; R22| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 9700 mg/kg. Fish LC50 for guppies 0.5, rainbow trout
0.050.5 mg/l. Bees LD50 (oral) 18.819.6 mg/kg.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, >90% of the dose is eliminated within
24 h, principally in the urine. The pricipal metabolites are the desmethyl compound and the
phenol (FAO/WHO datasheet 76 (1994)). Plants In tomato plants, the main metabolite is
the phenol (M. Stiasni et al., J. Agr. Fd. Chem. (1969) 17, 1017, cited by FAO/WHO 28).
bromophos-ethyl
IRAC1B Cl
S OCH2CH3
Br O P
OCH2CH3
Cl
NOMENCLATURE:
Common name bromophos-ethyl (BSI, E-ISO, F-ISO, ESA)
IUPACname O-4-bromo-2,5-dichlorophenyl O,O-diethyl phosphorothioate
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl)
O,O-diethyl phosphorothioate CASRN[4824786] ECno2253990
DevelopmentcodesS-2225 (Boehringer, Cela GmbH)
SmilescodeCCOP(=S)(OCC)Oc1cc(Cl)c(Br)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 394.1 M.f. C10H12BrCl2O3PS Form Colourless to
pale yellow liquid.
B.p. 122123C /0.00l mmHg V.p. 6.1 mPa (30C) S.g./density 1.521.55 (20C)
Solubility In water 0.14 mg/l (20C). Completely miscible with most common organic
solvents. Stability Stable in aqueous suspension at pH <9; hydrolysed at higher pH.
COMMERCIALISATION:
History Insecticide reported by M. S. Mulla etal. (Mosq. News, 1964, 24, 312), and reviewed
by D. Eichler (Residue Rev., 1972, 41, 65). Introduced by C. H. Boehringer Sohn/Cela GmbH
(later Shell Agrar GmbH). Patents DE 1174104; GB 956343
60 bromophos-ethyl
APPLICATIONS:
and acaricide with contact and stomach action. Uses Control of Diptera, Hemiptera,
some Lepidoptera, Coleoptera, some other insects, and mites in fruit, vegetables, field
crops, ornamentals, and forestry. Also used in public health for control of flies, mosquito
larvae, etc.; for control of insects in animal houses; and as an animal ectoparasiticide.
Formulation types EC; WP; GR; KN; UL . Compatibility Not compatible with sulfur
and organometallic compounds.
PRODUCTS:
Discontinued products Filariol* (Celamerck); Nexagan* (Shell).
ANALYSIS:
Product by oxidation with bromide-bromate solution, and titration of the excess bromate
with sodium thiosulfate (R. Weeren & D. Eichler Anal. Methods Pestic. Plant Growth Regul.
1978, 10, 3334). Residues by glc with phosphorus-specific FID (R. D. Weeren & D. Eichler
Anal. Methods Pestic. Plant Growth Regul. 1978, 10, 3540; D. C. Abbott et al., Pestic. Sci. 1970,
1, 10). Determination of the halogenated phenol produced by hydrolysis can be used for
both product and residue analysis.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. 29 (1977).
LD50 for rabbits 100600 mg/kg. Inhalation LC50 (1.7 h) for rats 2.5 mg/l. NOEL (2 y) for
rats 78 mg/kg daily, for dogs 0.26 mg/kg daily. ADI/RfD (JMPR) 0.003 mg/kg b.w. [1975].
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassification T; R25| Xn; R21| N;
R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for quail 200 mg/kg. Fish LC50 (96 h) for guppies 0.140.24, rainbow
trout >0.4 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, 8590% of the dose is eliminated
within 4 d in the faeces and urine. The principal metabolite is 4-bromo-2,5-dichlorophenol.
brompyrazon
Herbicide
NOMENCLATURE:
Common name brompyrazon (BSI (from 1984), E-ISO); brompyrazone (BSI (before
1984), (f) F-ISO)
brompyrazon 61
IUPACname 5-amino-4-bromo-2-phenylpyridazin-3(2H)-one
Chemical Abstracts name 5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone
CASRN[3042840] DevelopmentcodesBAS 2430H (BASF)
SmilescodeNc1cnn(c2ccccc2)c(=O)c1Br
PHYSICAL CHEMISTRY: Mol. wt. 266.1 M.f. C10H8BrN3O Form Yellowish
crystalline powder. M.p.223224C Solubility In water 200 mg/l (20C). In benzene 0.3,
chloroform 2, ethanol 11 (all in g/kg, 20C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Weed Res., 1962, 2, 177). Introduced by BASF AG.
APPLICATIONS:
ModeofactionSelective herbicide. Uses A mixture with isonoruron controls Alopecurus
myosuroides, Apera spica-venti and annual broad-leaved weeds pre-em. or post-em. in cereals.
PRODUCTS:
Discontinuedmixtures Basanor* (+isonoruron) (BASF).
Oral Acute oral LD50 for rats >6400 mg Basanor/kg. Skin and eye The formulation
caused only slight reddening 24 h after application to the shaved skin of rabbits.
ECOTOXICOLOGY:
Fish LC50 for guppies 1020 mg/l.
Details PM5, p. 55.
bromuron
Herbicide
NOMENCLATURE:
IUPACname N-(4-bromophenyl)-N-dimethylurea (I)
Chemical Abstracts name (I) CASRN[3408977] DevelopmentcodesFL 173
(Fahlberg-List)
PHYSICAL CHEMISTRY: Mol. wt. 243.1 M.f. C9H11BrN2O Form Colourless crystals.
M.p.172174C
V.p. 0.5 mPa (25C) Henry 5 105 Pa m3 mol1 (calc.) S.g./density 1.28 at 25C
Solubility In water 0.237 g/l (22.5C). In acetone 76.4, benzene 3.1, chloroform 35.8,
1,2-dichloroethane 7.2, hexane 0.4 (all in g/kg, 25C). Stability Stable under normal
conditions at pH 7. Decomposes in strong acids and alkalis. Stable to light.
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. Uses Pre-emergence control of annual weeds.
Used, preferably in combination with other herbicides, in potatoes and vegetables.
Formulation types WP
62 bromuron
PRODUCTS:
Discontinued products Faluron* (Fahlberg-List).
ANALYSIS:
Product and residue analysis by tlc (M. Koennig et al., Nachrichtenbl. Pflanzenschutz DDR
1987, 41, 55).
>20000 mg/kg. Non-irritating to skin. NOEL (90 d) for rats 5 mg/kg daily.
ECOTOXICOLOGY:
Fish LC50 (96 h) for guppies 112 mg/l; (48 h) for guppies 138 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 c.112118 d.
BTS 44584
O S+
O O-
O
N S
O
dimethyl(4-piperidinocarbonyloxy-2,5-xylyl)sulfonium toluene-4-sulfonate
NOMENCLATURE:
IUPACname dimethyl(4-piperidinocarbonyloxy-2,5-xylyl)sulfonium toluene-4-sulfonate
Chemical Abstracts name [2,5-dimethyl-4-[(4-piperidinylcarbonyl)oxy]
phenyl]dimethylsulfonium 4-methylbenzenesulfonate CASRN[68721608]
DevelopmentcodesBTS 44584 SmilescodeC[S+](C)c1cc(C)c(OC(=O)N2CCCCC2)
cc1C.Cc1ccc(cc1)S(=O)(=O)[O-]
COMMERCIALISATION:
History Plant growth regulator reported by J. F. Garrod etal. (Monograph Brit. Plant Growth
Regulator Group, 1980, No. 4, p. 67). Evaluated by Boots Co., Ltd (later Schering Agriculture).
Patents GB 1593541.
APPLICATIONS: Uses Retards growth of various crops, including beans,
chrysanthemums, cotton, soya beans and sunflowers. Formulation types SP.
Oral Acute oral LD50 for rats >400 mg/kg.
BTS 44584 63
bufencarb
Insecticide
NOMENCLATURE:
Common name bufencarbe ((m) F-ISO); bufencarb (for a reaction product) (BSI, E-ISO,
ANSI, ESA)
IUPACname of the main components are: (i) 3-(1-methylbutyl)phenyl methylcarbamate
(I); and (ii) 3-(1-ethylpropyl)phenyl methylcarbamate (II)
Chemical Abstracts name (I) and (II) CASRN[8065369] bufencarb; [2282340]
(i); [672048] (ii) DevelopmentcodesOrtho 5353
PHYSICAL CHEMISTRY:
Composition Produced by the action of methyl isocyanate on a reaction mixture of
alkylated phenols, tech. bufencarb comprisesc.65% of a 3:1 mixture of (i) and (ii) and 35%
of insecticidally-inactive related isomers (mainly the 2- and 4-alkyl analogues). Mol. wt.
221.3 M.f. C13H19NO2 Form Tech. mixture is a yellow to amber coloured solid. M.p.26
39C (tech.) B.p. c.125C /0.04 mmHg V.p. 4.0 mPa (30C) S.g./density 1.024 (26C,
tech.) Solubility In water <50 mg/l (room temperature).Very soluble in methanol, xylene;
less so in hexane. Stability Stable in acid or neutral solutions, but hydrolysis increases
with pH or temperature.
COMMERCIALISATION:
History Insecticide introduced by Chevron Chemical Company LLC. Patents US
3062864, US 3062867
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide with contact
and stomach action. Uses Insecticide, effective at 0.52.0 kg/ha against a range of soil-
and foliage-inhabiting insects, particularly Chilo plejadellus, Crambus caliginosellus larvae,
Dysmicoccus brevipes, Lissorhoptrus oryzophilus, Nephotettix nigropictus, rice planthoppers.
Formulation types DP; EC; GR .
PRODUCTS:
Discontinued products Bux* (Chevron); Bux Ten* (Chevron).
ANALYSIS:
Product analysis is by glc (B. Tucker, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 179).
Residues may be determined by glc (idem, ibid.) or by rplc (AOACMethods, 18th Ed.,
985.23). See also Pestic. Anal. Man., I, 401.
Oral Acute oral LD50 for rats 87 mg tech./kg. Skin and eye Acute percutaneous LD50 for
rabbits 680 mg/kg. Minimal eye irritation (rabbits). NOEL In 90 d feeding trials, no effect
was noted with beagle dogs and albino rats receiving 500 mg/kg diet.
64 bufencarb
Toxicity Class WHO (a.i.) II ECClassification T; R24/25| N; R50, R53

ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for pheasants and ducks >27000 mg/kg. Fish LC50 (96 h) for
goldfish 0.56, catfish 1.95, trout 0.064 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soil.
buminafos
NOMENCLATURE:
Common name buminafos (BSI, E-ISO, (m) F-ISO)
IUPACname dibutyl 1-butylaminocyclohexylphosphonate
Chemical Abstracts name dibutyl 1-(butylamino)cyclohexylphosphonate
CASRN[51249059] SmilescodeCCCCNC1(CCCCC1)P(=O)(OCCCC)OCCCC
PHYSICAL CHEMISTRY: Mol. wt. 347.5 M.f. C18H38NO3P M.p.c. 25C B.p.
9599C /1 mmHg V.p. c.100 mPa (20C) Henry 2 101 Pa m3 mol1 (20C, calc.)
S.g./density 0.969 (20C)
Solubility In water 170 mg/l (room temperature). Readily miscible with common organic
solvents (e.g. acetone, methanol, xylene, etc.). Immiscible with diesel oil.
Stability Hydrolysed by strong acids and alkalis. Aqueous hydrolysis DT50 13 d (pH 6),
20 h (pH 8), 2.75 h (pH 11).
COMMERCIALISATION:
History Plant growth regulator evaluated by VEB Chemiekombinat Bitterfeld. Later
marketed by Luxan B.V.
APPLICATIONS:
ModeofactionNon-selective contact herbicide, absorbed by the leaves and roots. Uses
Control of annual grass and broad-leaved weeds in vegetables, beet, ornamental plants and
shrubs, strawberries, herbs, fruit-tree nurseries, and land to be used for horticulture. Also
used for destruction of potato haulms; for cleaning and removal of side-shoots in hops; as
a cotton defoliant; and as a desiccant for Leguminosae and seed crops of brassicas, spinach,
onions, and beet. Formulation types EC.
PRODUCTS:
Discontinued products Trakefon* (Luxan); Trakephon* (Asepta).
ANALYSIS:
Product by nmr spectrophotometry. Residues by tlc.
buminafos 65
1200015000, rabbits 50008000 mg/kg. Irritating to skin and eyes. NOEL (130 d) for rats
140 mg/kg daily.
ECOTOXICOLOGY:
Fish LC50 (96 h) for guppies 7 mg/l. Bees Not hazardous to bees if used as directed.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, rapidly metabolised by dealkylation
at the oxygen and nitrogen atoms, followed by deamination. Soil/Environment Soil DT50
c.811 d.
butacarb
Insecticide
NOMENCLATURE:
Common name butacarb (BSI, E-ISO); butacarbe ((m) F-ISO)
IUPACname 3,5-di-tert-butylphenyl methylcarbamate
Chemical Abstracts name 3,5-bis(1,1-dimethylethyl)phenyl methylcarbamate
CASRN[2655198] DevelopmentcodesRD 14 639; BTS 14 639
SmilescodeCNC(=O)Oc1cc(cc(c1)C(C)(C)C)C(C)(C)C
COMMERCIALISATION:
History Acaricide reported by J. Fraser etal. (J. Sci. Food Agric., 1967, 18, 372), used as
mixture with gamma-HCH against animal ectoparasites. Introduced by Boots Co., Ltd
(later Schering Agrochemicals).
APPLICATIONS:
Details PM5, p. 59.
butathiofos
Insecticide
N
O
O
N P
O
S
O-2-tert-butylpyrimidin-5-yl O,O-diethyl phosphorothioate
66 butathiofos
IRAC1B
NOMENCLATURE:
Common name butathiofos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname O-2-tert-butylpyrimidin-5-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[2-(1,1-dimethylethyl)-5-pyrimidinyl] O,O-diethyl
phosphorothioate CASRN[90338208] DevelopmentcodesDowco 429; XRD 429
SmilescodeCCOP(=S)(OCC)Oc1cnc(nc1)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 304.4 M.f. C12H21N2O3PS Form Colourless oil.
B.p. 290C V.p. 22 mPa (25C) Kow logP = 4 (pH 7) Solubility In water 19.4 mg/l
(20C). In acetone, cyclohexanone, DMF, methanol, xylene >500, digol 98, propane-1,2-diol
58 (all in g/l, 20C).
COMMERCIALISATION:
History Insecticide evaluated by DowElanco.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses A pre-plant. treatment (c. 250 g/ha)
controls Diabrotica spp. and other soil-dwelling pests in maize. Formulation types GR .
PRODUCTS:
Discontinued products Butafos* (Dow).
ANALYSIS:
Product and residue analysis by hplc.
Oral Acute oral LD50 for mice 15, rats 3.2 mg/kg. Skin and eye Acute percutaneous LD50
for rats 12.625.2 mg/kg. NOEL (2 y) for rats 0.01 mg/kg daily.
ECOTOXICOLOGY:
Daphnia LC50 0.30 mg/l. Bees Acute toxicity to honeybees 7.7 ng/bee.
butenachlor
Herbicide
CH2CH3
COCH2Cl
N
CH2 O CH2 CH3
CH2CH3 C C
H H
NOMENCLATURE:
Common name but(nachlore) ((m) F-ISO); butenachlor (BSI, E-ISO)
IUPACname (Z)-N-but-2-enyloxymethyl-2-chloro-2,6-diethylacetanilide
butenachlor 67
Chemical Abstracts name (Z)-2-chloro-N-[(2-butenyloxy)methyl]-N-(2,6-

diethylphenyl)acetamide CASRN[87310563] DevelopmentcodesKH-218
SmilescodeCCc1cccc(CC)c1N(COCC=CC)C(=O)CCl
PHYSICAL CHEMISTRY: Mol. wt. 309.8 M.f. C17H24ClNO2 Form Light-yellow liquid.
M.p.12.9C B.p. 167C /399 Pa V.p. 0.93 mPa (25C) Kow logP = 3.51 (hplc method)
Henry 1 102 Pa m3 mol1 (calc.) S.g./density 1.0998 Solubility In water 29 mg/l
(27C). Miscible with acetone, ethanol, ethyl acetate, and hexane. Stability Stable in acidic,
neutral, and weakly alkaline media. Unstable in sunlight.
COMMERCIALISATION:
History Herbicide introduced by Agro-Kanesho Co., Ltd. Patents US 4798618; JP
1518580 Manufacturers Agro-Kanesho
APPLICATIONS:
Biochemistry Inhibits cell division by blocking protein synthesis. It is reported that
chloroacetamides inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr.
Meeting WSSA,Toronto, 40, 117118, 2000; P. Bger, Abstr. III Int.Weed Control Congr., Brazil,
2000). ModeofactionSelective herbicide, absorbed primarily by germinating shoots, and
secondarily by roots, with translocation throughout the plant, giving higher concentrations
in vegetative parts than in reproductive parts. Uses Pre-emergence control of most grass
and some broad-leaved weeds, and many aquatic weeds, in both seeded and transplanted
rice at 0.751.0 kg/ha. Formulation types GR .
ANALYSIS:
Product analysis by glc. Residues determined by glc with NPD.
Oral Acute oral LD50 for male rats 1630, female rats 1875, male mice 6417, female mice
6220 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Slightly
irritating to eyes and skin. Inhalation LC50 (4 h) for rats 3.34 mg/l air. NOEL (90 d) for
rats 20, dogs 25 mg/kg. Non-teratogenic and no reproductive effects evident.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2000 mg/kg. Fish LC50
(96 h) for mirror carp 0.48, Japanese killifish 0.42 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 25 d.
buthidazole
Herbicide
NOMENCLATURE:
Common name buthidazole (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-methyl-2-imidazolidone
68 buthidazole
Chemical Abstracts name 3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-

1-methyl-2-imidazolidinone CASRN[55511983] DevelopmentcodesVel-5026
SmilescodeCN1CC(O)N(C1=O)c2nnc(s2)C(C)(C)C
PHYSICAL CHEMISTRY:
Composition Tech. is 86%. Mol. wt. 256.3 M.f. C10H16N4O2S Form Colourless crystals;
(tech. is a tan powder). M.p.133134C V.p. 0.0053 mPa (25C) Henry 2.09 10-7 Pa
m3 mol1 (calc.)
S.g./density 1.28 (25C) Solubility In water 6.5 g/kg (25C). In acetone 150, DMF
208, toluene 45, xylene, 10 (all in g/kg, 25C). Stability Decomposes at 237C; relatively
resistant to uv degradation.
COMMERCIALISATION:
History Herbicide reported by R. F. Anderson (Proc. Int.Velsicol Symp., 8th, 1974).
Introduced by Velsicol Chemical Corp. (later Sandoz AG). Patents US 3904640
APPLICATIONS:
ModeofactionContact herbicide. Uses Residual pre- and post-emergence herbicide
in industrial and non-crop areas at 4.56.5 kg/ha depending on rainfall. Used at lower
rates against broad-leaved weeds and annual grasses in maize, pineapple and sugar cane.
Formulation types GR; WP.
PRODUCTS:
Discontinued products Ravage* (Sandoz).
ANALYSIS:
Product analysis and soil residue determinations are by hplc.
for rabbits >20000 mg/kg. Non-irritant to skin and eyes (rabbits). Inhalation LC50 (4 h)
for rats >20.8 mg/l (dust). NOEL (2 y) for rats 300 mg/kg diet; liver tumours reported in
mice at 1000 mg/kg diet. Not teratogenic in rabbits at 90 mg/kg daily. NOEL for rats
(3 generations) 1500 mg/kg diet. Other Non-mutagenic to mammalian cells.
Toxicity Class WHO (a.i.) III
ENVIRONMENTAL FATE:
Soil/Environment DT50 >50 d.
buthiobate
Fungicide
NOMENCLATURE:
Common name buthiobate (BSI, E-ISO, (m) F-ISO)
IUPACname butyl 4-tert-butylbenzyl N-(3-pyridyl)dithiocarbonimidate
Chemical Abstracts name butyl [4-(1,1-dimethylethyl)phenyl]methyl
buthiobate 69
3-pyridinylcarbonimidodithioate CASRN[51308544] DevelopmentcodesS-1358

(Sumitomo Chemical) SmilescodeCCCCSC(=Nc1cccnc1)SCc2ccc(cc2)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 372.6 M.f. C21H28N2S2 Form Tech. is a red-brown
viscous liquid. M.p.3133C (tech.) V.p. 0.06 mPa (20C) S.g./density 1.0865 (25C,
tech.) Solubility In water 1 mg/l (25C). In methanol and xylene >1 kg/kg (23C).
COMMERCIALISATION:
History Fungicide reported by T. Kato etal. (Agric. Biol. Chem., 1975, 39, 169). Introduced by
Sumitomo Chemical Co., Ltd. Patents GB 1335617; US 3832351
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor. ModeofactionFungicide with
protective and curative action, and long persistence. Uses Fungicide with rain fastness. It
was effective against powdery mildew on beans, fruit, ornamentals, vegetables and other
crops. Applied at 15250 mg/l. Phytotoxicity Some varieties of beans may be injured at
high concentrations. Formulation types EC; WP.
PRODUCTS:
Discontinued products Denmert* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc (S. Irie et al., Nippon Nogei Kagaku Kaishi, 1977, 51, 331).
Oral Acute oral LD50 for male rats 4400, female rats 3200 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >5000 mg/kg. Not a skin or eye irritant (rabbits).
Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >10000, bobwhite quail 21800 mg/kg. Fish LC50
(48 h) for carp 6.4 mg/l.
buthiuron
Herbicide
NOMENCLATURE:
Common name buthiuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(5-butylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
Chemical Abstracts name N-[5-(butylsulfonyl)-1,3,4-thiadiazol-2-yl]-N,N-dimethylurea
CASRN[30043551] DevelopmentcodesMET 1489
SmilescodeCCCCS(=O)(=O)c1nnc(s1)N(C)C(=O)NC
PHYSICAL CHEMISTRY: Mol. wt. 292.4 M.f. C9H16N4O3S2
COMMERCIALISATION:
70 buthiuron
butocarboxim
IRAC1A; oxime carbamate
CH3 NH
C O CH3 CH3
O N C O N C
CH SCH3 C O CH SCH3
CH3 CH3 NH CH 3
(E)- (Z)-
NOMENCLATURE:
Common name butocarboxim (BSI, E-ISO); butocarboxime ((f) F-ISO)
IUPACname 3-(methylthio)butanone O-methylcarbamoyloxime
Chemical Abstracts name 3-(methylthio)-2-butanone O-[(methylamino)carbonyl]oxime
CASRN[34681102] ECno2521393 DevelopmentcodesCo 755 (Wacker)
SmilescodeCNC(=O)ON=C(C)C(C)SC
PHYSICAL CHEMISTRY:
Composition Tech. grade is liquid and obtained as an 85% tech. concentrate in xylene
containing the (E)- and (Z)- isomers in a ratio of 8590:1510. Mol. wt. 190.3 M.f.
C7H14N2O2S Form Pale brown, viscous liquid (tech.). Crystalline at lower temperatures.
M.p.37C ((E)- isomer); ((Z)- isomer is an oil at room temperature) V.p. 10.6 mPa
(20C) (tech., without residual xylene) Kow logP = 1.1 Henry 5.76 105 Pa m3 mol1
(calc.) S.g./density 1.12 (20C) Solubility In water 35 g/l (20C). Completely miscible
with aromatic hydrocarbons, esters, and ketones. Low solubility in aliphatic hydrocarbons
(11 g/l) and carbon tetrachloride. Stability Stable at pH 57 (up to 50C), but hydrolysed
by strong acids and alkalis. Stable to sunlight and oxygen. Thermally stable up to 100C.
COMMERCIALISATION:
History Insecticide reported by M.Vulic etal. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1973, 38, 1175). Structure/activity of analogues discussed (T. A. Magee & L. E. Limpel, J. Agric.
Food Chem., 1977, 25, 1376). Introduced by Wacker-Chemie GmbH. Patents DE 2036491;
US 3816532; GB 1353202
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide with
contact and stomach action. Absorbed by the leaves and roots. Uses Control of aphids,
thrips, whiteflies, mealybugs, and other sucking insects (with secondary action against
spider mites) on fruit trees (including citrus), vegetables, cereals, cotton, hops, tobacco, and
ornamentals (including ornamentals cultivated by hydroponics). Formulation types AE;
EC; SL .
butocarboxim 71
PRODUCTS:
Discontinued products Drawin* (Wacker); Hydrosekt* (Luxan).
ANALYSIS:
Product analysis by i.r. spectrometry or by hplc. Residues of butocarboxim, its sulfoxide
and sulfone (butoxycarboxim) determined by glc with TID. Details available from Wacker-
Chemie GmbH.
EHC 64 (1986) is a general review of pesticides with a carbamate chemical structure.
JMPR Evaln. I 48 (1986). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
for albino rabbits 360 mg/kg. Irritating to eyes. Inhalation LC50 (4 h) for rats 1 mg/l air.
NOEL (2 y) for rats 100 mg/kg diet; (90 d) for dogs 100 mg/kg diet. No carcinogenic or
mutagenic activity in routine tests at the highest dose (300 mg/kg diet) in rats during 2 y,
nor any effect on fertility, growth rate or mortality. ADI/RfD (JMPR) No ADI [1985]; (BfR)
0.02 mg/kg b.w. [1990]. Other Not mutagenic in the Ames assay. Toxicity Class WHO
(a.i.) Ib EPA (formulation) II ECClassification R10| T; R23/24/25| Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds LD50 for mallard ducks 64 mg/kg. LC50 (8 d) for Japanese quail 1180 mg/kg diet.
Fish LC50 (96 h) for rainbow trout 29 mg/l. LC50 (24 h) for rainbow trout 35, goldfish 55,
guppies 70 mg/l. Daphnia LC50 (24 h) 3.25.6 mg/l. Algae NOEL for Algae 62.5 mg/l.
Bees Toxic to bees; LD50 1 g/bee.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolised to butoxycarboxim, and
excreted in the urine as butoxycarboxim and its degradation products. Plants In plants,
degradation is the same as in soil. Soil/Environment In soil, the methylamine moiety is
split off, and the sulfur atom is oxidised to sulfoxide and sulfone. DT50 in soil 18 d; DT50
for metabolites 1644 d.
butonate
Insecticide
IRAC1B
NOMENCLATURE:
Common name butonate (BSI, E-ISO, (m) F-ISO); butilchlorofos* (former exception
USSR) IUPACname 2,2,2-trichloro-1-(dimethoxyphosphinoyl)ethyl butyrate
Chemical Abstracts name 2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl butanoate
CASRN[126227] SmilescodeCCCC(=O)OC(C(Cl)(Cl)Cl)P(=O)(OC)OC
72 butonate
PHYSICAL CHEMISTRY: Mol. wt. 327.5 M.f. C8H14Cl3O5P

COMMERCIALISATION:
History Insecticide reported by B. W. Arthur & J. E. Casida (J. Agric. Food Chem., 1958, 6,
360). Introduced by Prentiss Drug & Chemical Co.
APPLICATIONS:
Details PM4, p. 61.
butopyronoxyl
Insect repellent
NOMENCLATURE:
Common name butopyronoxyl (US Pharmacopoeia)
IUPACname butyl 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylate (I)
Chemical Abstracts name (I) Other names dihydropyrone; butyl mesityloxide oxalate
CASRN[532343] SmilescodeCCCCOC(=O)/C/1=C/C(=O)CC(C)(C)O1;
without stereochemistry: CCCCOC(=O)C1=CC(=O)CC(C)(C)O1
PHYSICAL CHEMISTRY:
Composition Tech. contains 85% butopyronoxyl with 2% mesityl oxide; the remainder
is mainly dibutyl oxalate and butanol. It exists mainly as the dihydropyrone (I) but with the
open chain enol (II) in equilibrium (S.A. Hall et al., J. Am. Chem. Soc., 1945, 67, 1224). Mol. wt.
226.3 M.f. C12H18O4 Form Yellow to pale red liquid with a mild aromatic odour. B.p. 90%
distils between 256270C S.g./density 1.0521.060 (20C)
Solubility Practically insoluble in water and glycerol. Slightly soluble in ethylene glycol,
refined petroleum oils; miscible with chloroform, ethanol, diethyl ether, glacial acetic acid.
COMMERCIALISATION:
History Insect repellent introduced by US Industrial Chemicals Inc. and by Kilgore
Chemicals. Patents US 2138540
PRODUCTS:
Discontinued products Indalone* (FMC).
Oral Acute oral LD50 for rats 7840, guinea pigs 3200 mg/kg. Skin and eye Acute
percutaneous LD50 for rabbits 10000 mg/kg. Not a skin irritant but may cause a stinging
sensation. NOEL In 2 y feeding trials, some growth retardation was observed in rats
receiving 80 g/kg diet. Toxicity Class WHO (a.i.) U
Details PM6, p. 66.
butopyronoxyl 73
2-(2-butoxyethoxy)ethyl piperonylate
NOMENCLATURE:
IUPACname 2-(2-butoxyethoxy)ethyl piperonylate
Chemical Abstracts name 2-(2-butoxyethoxy)ethyl 1,3-benzodioxole-5-carboxylate
Other names BCP CASRN[136630]
SmilescodeCCCCOCCOCCOC(=O)c1ccc2OCOc2c1
COMMERCIALISATION:
History Synergist for pyrethrum introduced by Bush Boake & Allen.
APPLICATIONS: Uses A pyrethrum synergist.
PRODUCTS:
Discontinued products Bucarpolate* (Bush Boake & Allen).
2-(2-butoxyethoxy)ethyl thiocyanate
Insecticide
NOMENCLATURE:
IUPACname 2-(2-butoxyethoxy)ethyl thiocyanate (I)
Chemical Abstracts name (I) Other names butyl Carbitol thiocyanate; butyl
Carbitol rhodanate; beta-butoxy-beta-thiocyanodiethyl ether CASRN[112561]
SmilescodeCCCCOCCOCCSC#N
COMMERCIALISATION:
History Insecticide reported by D. F. Murphy & C. H. Peet (J. Econ. Entomol., 1932, 25, 123).
Introduced by Rohm & Haas Co.
PRODUCTS:
Discontinued products Lethane 384* (Rohm & Haas).
ECClassification R10| T; R24/25
butoxy(polypropylene glycol)
Insect repellent
NOMENCLATURE:
Common name butoxy(polypropylene glycol) (ESA)
IUPACname -hydroxypropyl-o-butoxypoly[oxy(1-methylethylene)]
Chemical Abstracts name -butyl-o-hydroxypoly[oxy(methyl-1,2-ethanediyl)]
74
butoxy(polypropylene glycol)
CASRN[9003138]
COMMERCIALISATION:
History Fly repellent. Introduced by Union Carbide Corp.
PRODUCTS:
Discontinued products Crag Fly Repellent* (Union Carbide).
butroxydim
Herbicide
CH3 O OCH2CH3
N
CH3
CH2CH3
CH3(CH2)2 CH3 OH
O
HRACA WSSA 1; cyclohexanedione oxime
NOMENCLATURE:
Common name butroxydime ((m) F-ISO); butroxydim (BSI, E-ISO)
IUPACname 5-(3-butyryl-2,4,6-trimethylphenyl)-2-(1-ethoxyiminopropyl)-3-
hydroxycyclohex-2-enone
Chemical Abstracts name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,4,6-trimethyl-
3-(1-oxobutyl)phenyl]-2-cyclohexen-1-one CASRN[138164122] ECno4147903
DevelopmentcodesICIA0500 (ICI)
SmilescodeCCCC(=O)c1c(C)cc(C)c(C2CC(=C(C(=NOCC)CC)C(=O)C2)O)c1C
PHYSICAL CHEMISTRY: Mol. wt. 399.5 M.f. C24H33NO4 Form Off-white powdery
solid. M.p.80.8C
V.p. 1 103 mPa (20C) Kow logP = 1.90 (pH 7, 25C) Henry 5.79 105 Pa m3 mol1
(calc.) S.g./density 1.20 (tech., 25C) Solubility In water 6.9 mg/l (pH 5.5, 20C). In
dichloromethane >500, acetone 450, toluene 480, acetonitrile 380, methanol 90, hexane 30
(all in g/l). Stability Hydrolysis DT50 10.5 d (pH 5), >240 d (pH 7), stable (pH 9) (all 25C).
pKa 4.36 (23C), weak acid
COMMERCIALISATION:
History First sold in 1995. Divested to Crop Care Australasia Pty Ltd in 2002.
APPLICATIONS:
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase
(ACCase). ModeofactionPost-emergence herbicide. Uses A post-emergence grass
herbicide for use on broad-leaved crops, at 2575 g/ha. Formulation types WG .
PRODUCTS:
Discontinued products Falcon* (Crop Care).
butroxydim 75
ANALYSIS:
Residues determined by hplc with uv detection, or by hplc-ms.
Oral LD50 for male rats 3476, female rats 1635 mg/kg. Skin and eye Acute percutaneous
LD50 for rats >2000 mg/kg. Moderate skin irritant; mild eye irritant (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >2.99 mg/l. NOEL NOAEL (1 y)
for dogs 5 mg/kg b.w. daily; NOEL (2 y) for rats 2.5, mice 10 mg/kg b.w. daily (liver tumours
only in males at high dose); NOEL developmental for rats 5, rabbits 15 mg/kg b.w. daily.
ADI/RfD 0.025 mg/kg. Other Genotoxicity negative. Not oncogenic (rats).
Toxicity Class WHO (a.i.) III. ECClassification (T; R61| R22| R38| N; R50, R53)
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >2000, bobwhite quail 1221 mg/kg. Sub-acute
dietary LC50 (5 d) for mallard ducks >5200, bobwhite quail 5200 mg/kg. Fish LC50 (96 h)
for rainbow trout >6.9, bluegill sunfish 8.8 mg/l. Daphnia LC50 (48 h) >3.7 mg/l. Algae
EbC50 for Selenastrum capricornutum 0.71 mg/l. Bees LD50 (contact, 24 h) >200 g/bee.
Worms LC50 (14 d) for Eisenia foetida >1000 mg/kg.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, >90% of the dose is excreted within 7 d.
Various oxidative transformations of the butyryl chain dominate the metabolic pathway.
Neither parent nor metabolites bioaccumulate in tissues. Plants Rapidly metabolised
in plants. Soil/Environment Soil Koc 61270 (stronger adsorption in low pH soils).
Rapid degradation in aerobic soil, lab. DT50c.9 d (20C, 40% MHC, pH 7.0, 4.09% o.m.);
metabolites include 5-(3-butyryl-2,4,6-trimethylphenyl)-3-hydroxy-2-(1-iminopropyl)
cyclohex-2-enone, 6-(3-butyryl-2,4,6-trimethylphenyl)-2-ethyl-4,5,6,7-tetrahydro-4-oxo-
1,3-benzoxazole, 2-(3-butyryl-2,4,6-trimethylphenyl)glutaric acid and 5-(3-butyryl-2,4,6-
trimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-enone.
buturon
Herbicide
NOMENCLATURE:
Common name buturon (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(4-chlorophenyl)-1-methyl-1-(1-methylprop-2-ynyl)urea
Chemical Abstracts name N-(4-chlorophenyl)-N-methyl-N-(1-methyl-2-propynyl)urea
CASRN[3766607] DevelopmentcodesH 95 (BASF) SmilescodeCC(C#C)N(C)
C(=O)Nc1ccc(Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 236.7 M.f. C12H13ClN2O Form Colourless solid.
M.p.145146C; (tech., 132142C) V.p. 0.01 mPa (20C) Henry 7.89 105 Pa m3
mol1 (calc.) Solubility In water 30 mg/l (20C). In acetone 279, benzene 9.8, methanol
128 (all in g/kg, 20C).
76 buturon
Stability Stable under normal conditions (1<pH<13), but slowly decomposes in boiling
water.
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Meded. Landbouwhogesch. Opzoekingsstn. Staat
Gent, 1964, 29, 719). Introduced by BASF AG. Patents DE 1108977
APPLICATIONS:
Biochemistry Inhibits photosynthesis. ModeofactionSelective, systemic herbicide;
uptake is predominantly via the roots. Uses A pre-em. and post-em. herbicide, absorbed
mainly by the roots and recommended for use at 0.51.5 kg/ha in cereals and maize for
the control of shallow-germinating grasses and broad-leaved weeds. Formulation types
WP.
PRODUCTS:
Discontinued products Eptapur* (BASF); Discontinuedmixtures Basfitox*
(+isonoruron) (BASF).
ANALYSIS:
Product analysis by hydrolysis and potentiometric titration of the 4-chloroaniline produced.
Residues determined by hydrolysis and colorimetric estimation of the 4-chloroaniline
produced.
Oral Acute oral LD50 for rats 3000 mg/kg. Skin and eye Applications (20 h) to the backs
of rabbits produced a slight erythema but the ears were unaffected. NOEL In 120d
feeding trials, rats receiving 500 mg/kg diet showed no ill-effect. Other I.p. LD50 for mice
c.500 mg/kg. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Plants It is rapidly degraded in plants. Soil/Environment In soil, bacterial degradation
under the influence of CO2, probably involving 4-chloroaniline formation. Twelve weeks
after use, no active substance is biologically detectable.
sec-butylamine
Fungicide
CH3CH2CH(CH3)NH2
NOMENCLATURE:
Common name (RS)-sec-butylamine (proposed E-ISO, in lieu of a common name)
IUPACname (RS)-sec-butylamine; (RS)-2-aminobutane
Chemical Abstracts name 2-butanamine CASRN[13952846] (RS)-sec-butylamine;
sec-butylamine 77
[13250129] (R)-sec-butylamine; [513495] (S)-sec-butylamine ECno2377327 (RS)-

isomer; 2362326 (R)- isomer; 2081647 (S)- isomer
SmilescodeCCC(C)N
PHYSICAL CHEMISTRY:
Composition Tech. is 99%. Mol. wt. 73.1 M.f. C4H11N Form Colourless liquid, with
an ammoniacal odour. M.p.<100C B.p. 6365C V.p. 18 kPa (20C) Kow logP =
0.74 S.g./density 0.724 (20C) Solubility Miscible with water and with most organic
solvents. With acids, forms water-soluble salts. Stability Stable at room temperature.
Exothermic reaction with acids. pKa Base, forming water-soluble salts with acids. F.p.
19.5C (DIN 51755)
COMMERCIALISATION:
History Fungicidal properties of this fumigant reported by J. W. Eckert & M. J. Kolbezen
(Nature (London), 1962, 194, 188). Introduced by BASF AG in 1971; registration transferred
to Hortichem in 1992 (now Certis UK).
APPLICATIONS:
ModeofactionFumigant fungicide. Uses Fungicidal fumigation of seed and ware
potatoes for control of skin spot and gangrene. As fungicidal dips or sprays on harvested
fruit, e.g. control of citrus blue and green moulds and stem rot of oranges. Prevention of
Botrytis on chrysanthemums and gladioli during storage and transit.
Formulation types SL .
PRODUCTS:
Discontinued products Butafume* (BASF); Deccotane* (post-harvest) (Decco
Cerexagri); Tutane* (DowElanco).
ANALYSIS:
Product analysis by acid-base titration. Residues determined by glc of a derivative (Anal.
Methods Pestic. Plant Growth Regul., 1976, 8, 251; E. W. Day et al., J. Assoc. Off. Anal. Chem., 1968,
51, 39; Resid. Anal. Methods). See also Pestic. Anal. Man., II, 186.450.
JMPR Evaln. 37 (1981). ICSC.401 (1999). EU Status (1107/2009) Not approved,
Oral Acute oral LD50 for rats 380, dogs 225 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits >2500 mg/kg. Irritating to skin and eyes. Inhalation Vapours dangerous if
inhaled. NOEL In 2 y feeding trials, teratogenicity studies, reproduction studies, rats and
dogs receiving 2500 mg/kg diet suffered no ill-effect. In teratogenicity studies, NOEL: for
rats 2500 mg/kg diet; for rabbits 5000 mg/kg diet. In reproduction studies in rats, NOEL
2500 mg/kg diet. ADI/RfD (JMPR) Temporary ADI withdrawn [1984].
Toxicity Class WHO (a.i.) II. ECClassification F; R11| Xn; R20/22| C; R35| N; R50 (for
(R)-, (S)-, or (RS)- isomers)
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 250 mg/kg. Fish LC50 for young bluegill sunfish >50 mg/l.
Daphnia EC50/LC50 (48 h) 40.4 mg/l. Algae EC50/LC50 (72 h) 0.54 mg/l.
78 sec-butylamine
cadmium calcium copper zinc chromate sulfate

Fungicide
NOMENCLATURE:
IUPACname cadmium calcium copper zinc chromate sulfate (I)
DevelopmentcodesFungicide 531
COMMERCIALISATION:
History Fungicide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Crab Turf Fungicide* (Union Carbide).
EHC 200 (1998) is a general review of copper and copper compounds.
calcium and lead arsenate

Herbicide, insecticide
NOMENCLATURE:
Chemical Abstracts name tricalcium arsenate CASRN[7778441]; [7778394]
(arsenic acid)
PHYSICAL CHEMISTRY: Mol. wt. 398.1 M.f. As2Ca3O8 M.p.35C (arsenic acid)
V.p. 0.0 (for acid or salt?) Solubility Insoluble in water and organic solvents. The wettable
powder, when made up in aqueous solution, should contain less than 0.5% of dissolved
As2O5, which originates from impurities. Stability Moisture and carbon dioxide cause slow
decomposition to calcium carbonate and (phytotoxic) dicalcium hydrogen arsenate. In the
presence of acids, water-soluble, strongly phytotoxic arsenic acid is produced. pKa pKa1
2.3, pKa2 7.1 (J. Ag. & Food Chem., 24, 717 (1976)) (for acid).
APPLICATIONS: Uses Pre-emergence herbicidal treatment of turf and lawns to
control crabgrass. Controls chickweed, annual bluegrass, and certain soil insects, including
Japanese beetle. Phytotoxicity Foliage of stone fruit is particularly susceptible. Plant
damage can occur in the presence of water-soluble arsenic compounds. Formulation
types DP; WP; RB; GR .
PRODUCTS:
Discontinued products Pencal* (Pennwalt); Security* (Woolfolk); Security*
(Woolfolk).
ANALYSIS:
Product analysis described (AOACMethods, 18th Ed., 921.05, 921.06, 922.03, 925.03,
963.06); lead arsenate ibid., 920.16920.21. Residue analysis by mineralisation of the sample,
distillation of the arsenic, and determination colorimetrically at 540 nm, as the arsine
complex with silver diethyldithiocarbamate (Man. Pestic. Residue Anal., 230).
calcium and lead arsenate 79


EHC 224 (2001). JMPR Evaln. 11 (1968), 31 (1978) for lead arsenate. HSG 70 (1992).
ICSC.765 (1999) for calcium arsenate; ICSC.911 (1997) for lead arsenate. IARC 87 (2006)
(inorganic lead); 23 (1980), Suppl 7 (1987) (arsenic compounds).
IARC Class 1 (evaluation applies to arsenic compounds as a whole, not necessarily to all
individual compounds within the group); 2A (inorganic lead)
Oral Acute oral LD50 for rats 20 mg/kg; (lead saltc.10 mg/kg). NOEL 0.42 mg/kg b.w. (EPA
Tracking). ADI/RfD (JMPR) No ADI [1968], also for lead salt; (EPA) 0.0042 mg/kg b.w.
[1968]. Other Acute oral LD50 for rats 20, rabbits 50, dogs 38 mg/kg. Dermal resorption is
minimal. Toxicity Class WHO (a.i.) Ib (also for lead salt)
ECClassification R45| T; R23/25| N; R50, R53 (for arsenic acid and salts)
ECOTOXICOLOGY:
Fish Very toxic to fish. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Inorganically-bound arsenic remains unchanged for a long time in the
soil. The alleged microbial reduction to arsine and volatilisation is disputed.
calcium cyanamide
Fertiliser, fungicide, herbicide
NOMENCLATURE:
IUPACname calcium cyanamide
Chemical Abstracts name calcium cyanamide CASRN[156627]
ECno2058618 Smilescode[Ca+2].[N-]=C=[N-]
PHYSICAL CHEMISTRY: Mol. wt. 80.10 M.f. CCaN2 M.p.c. 1200C (sublimes
11501200C)
S.g./density 2.29 (420C) Solubility Insoluble in water, but gradually hydrolyses.
Insoluble in organic solvents. Stability Very stable under dry storage conditions.
Decomposed in moist conditions and in the presence of acids, to calcium hydrogen
cyanamide, cyanamide, and urea.
COMMERCIALISATION:
History Used as a fertiliser since 1905. Later introduced as herbicide and defoliant by
American Cyanamid Co., but these uses now discontinued.
APPLICATIONS:
ModeofactionPre- and post-emergence herbicide and defoliant, with secondary
fungicidal action. Produces hydrogen cyanamide upon contact with soil moisture, which
is toxic to plants, seeds, and disease organisms. Uses Fertiliser with secondary control of
weeds in cereals, maize, vines, field crops, vegetables, and in meadows and pastures. Also
fungicidal control of eyespot in cereals, and club root in brassicas. Cyanamide (q.v. in Main
80 calcium cyanamide
entries) is used as a herbicide and plant growth regulator. Phytotoxicity The chlorophyll
of most plants is sensitive, especially in humid conditions. Formulation types GR .
PRODUCTS:
Discontinued products Cyanamid* (Cyanamid).
ANALYSIS:
Product analysis by determination of nitrogen by the Kjeldahl process. Residues in
soil by extraction with 0.1 N hydrochloric acid, distillation, clean-up on aluminium
oxide and determination of the red complex formed with Na2NH4[Fe(CN)5NH3]
spectrophotometrically at 530 nm.
ICSC.639 (2006) EU Status (1107/2009) Vote for non-inclusion, SCFCAH 05/2008.
Oral Acute oral LD50 for rats 1400 mg/kg. Skin and eye Mild skin irritant.
Inhalation LC50 (4 h) for rats >0.15 mg/l air. Irritation of the mucous membranes of the
respiratory tract is evident after inhalation of the dust. Toxicity Class WHO (a.i.) O
ECClassification Xn; R22| Xi; R37, R41
ECOTOXICOLOGY:
Fish Not significantly toxic to fish provided the pH of the water does not exceed 88.5.
ENVIRONMENTAL FATE:
Soil/Environment Taken up into plants and fermentatively degraded. After 9 days, no
cyanamide nitrogen is detectable in potatoes.
Details PM5, p. 72.
cambendichlor
Herbicide
NOMENCLATURE:
Common name cambendichlor (BSI, E-ISO, ANSI, WSSA); cambendichlore ((m) F-ISO)
IUPACname 2,2-(phenylimino)diethylene bis(3,6-dichloro-o-anisate)
Chemical Abstracts name (phenylimino)di-2,1-ethanediyl bis(3,6-dichloro-
2-methoxybenzoate) CASRN[56141005] DevelopmentcodesVel 4207
SmilescodeCOc1c(Cl)ccc(Cl)c1C(=O)OCCN(CCOC(=O)c2c(Cl)ccc(Cl)c2OC)
c3ccccc3
PHYSICAL CHEMISTRY: Mol. wt. 587.3 M.f. C26H23Cl4NO6
COMMERCIALISATION:
History Herbicide introduced by Velsicol Chemical Corp. (later Sandoz AG).
cambendichlor 81
camphechlor
Insecticide
NOMENCLATURE:
Common name polychlorcamphene (USSR); camphechlor (BSI, E-ISO); camph(chlore)
((m) F-ISO); toxaphene (Belgium, Canada, USA)
IUPACname a reaction mixture of chlorinated camphenes containing 6769% chlorine
Chemical Abstracts name toxaphene CASRN[8001352] ECno2322833
DevelopmentcodesHercules 3956
PHYSICAL CHEMISTRY:
Composition Composition examined by J. E. Casida etal. (J. Agric. Food Chem., 1974,
22, 653; 1975, 23, 991); 26 components account for about 40% of the product. Mol.
wt. 431.8 (approx.) M.f. C10H10Cl8 (approx.) Form A yellow wax of mild terpene-like
odour. M.p.Softens 7095C V.p. 2700053000 mPa (25C) S.g./density 1.65 (25C)
Solubility In water c.3 mg/l (room temperature). Readily soluble in organic solvents
including petroleum oils. Stability Dehydrochlorinated by heat, by strong sunlight and by
certain catalysts such as iron.
COMMERCIALISATION:
History Insecticide reported by W. LeRoy Parker & J. R. Beacher (Del. Univ. Agric. Exp. Stn.
Bull., 1947, No. 264). Introduced by Hercules Inc. Patents US 2565471; US 2657164
APPLICATIONS:
ModeofactionNon-systemic, contact and ingested insecticide with some acaricidal
action. Uses Control of many insects in cereals, cotton, fruit, maize, vegetables and the
control of Cassia obtusifolia in soya beans. Has also been used for the control of animal
ectoparasites. A heptachlorobornane and a mixture of two octachlorobornanes are
more toxic to insects and mice than other components, and are similarly biodegradable.
Phytotoxicity Phytotoxic to cucurbits and some varieties of plum and damson.
Formulation types EC. Compatibility Not compatible with strongly alkaline pesticides.
PRODUCTS:
Discontinued products Agronex Hepta* (Epro); Altox* (Hercules); Attac* (BFC);
Toxaphene* (except in countries where used as common name) (Hercules).
ANALYSIS:
Product analysis by total chlorine (CIPACHandbook, 1970, 1, 132) or by tlc (AOACMethods
18th Ed., 972.05). Residues determined by glc with ECD (Anal. Methods Pestic. Plant Growth
Regul., 1972, 6, 514), by gel permeation chromatography and glc (AOACMethods, 14th Ed.,
29.03729.043) or by spectrometry of a derivative (C. L. Dunn, Anal. Methods Pestic., Plant
Growth Regul. Food Addit., 1964, 2, 523). See also Pestic. Anal. Man., I, 208, 504.
EHC 45 (1984). JMPR Evaln. 21 (1973). HSG 40 (1990). PDS 20 (1975). ICSC.843 (1997).
IARC 79 (2001). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 83/131/EEC and by Commission
Regulation 850/2004.
82 camphechlor
IARC Class 2B
rats 7801075 mg/kg. NOEL (2 y) for dogs 10 ppm (0.25 mg/kg b.w.) (EPA Tracking).
ADI/RfD (JMPR) No ADI [1973]; (EPA) 0.00025 mg/kg b.w. [1986]. Water GV Excluded
from GV derivation (U). Toxicity Class WHO (a.i.) II ECClassification R40| T; R25| Xn;
R21| Xi; R37/38| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Toxic to birds. Fish LC50 for young rainbow trout 0.2, young pike 0.1 mg/l.
Bees Low toxicity to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, camphechlor accumulates temporarily
in body fat, but is rapidly eliminated, partly as the unchanged substance and partly as
dechlorinated and partially dechlorinated metabolites. Soil/Environment In soil, becomes
tightly bound and is highly resistant to leaching. Persistent in soil (DT50 varies between 70 d
and 12 y, depending on soil type and climate).
carbamorph
Fungicide
NOMENCLATURE:
Common name carbamorph (BSI, E-ISO); carbamorphe ((m) F-ISO)
IUPACname morpholinomethyl dimethyldithiocarbamate
Chemical Abstracts name 4-morpholinylmethyl dimethylcarbamodithioate
CASRN[31848110] DevelopmentcodesMC 833
SmilescodeCN(C)C(=S)SCN1CCOCC1
PHYSICAL CHEMISTRY: Mol. wt. 220.4 M.f. C8H16N2OS2
COMMERCIALISATION:
History Fungicide introduced by Murphy Chemical Co. (later DowElanco).
carbanolate
Insecticide, ixodicide
NOMENCLATURE:
Common name carbanolate (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPACname 6-chloro-3,4-xylyl methylcarbamate
carbanolate 83
Chemical Abstracts name 2-chloro-4,5-dimethylphenyl methylcarbamate

CASRN[671045] DevelopmentcodesU 12 927
SmilescodeCNC(=O)Oc1cc(C)c(C)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 213.7 M.f. C10H12ClNO2
COMMERCIALISATION:
History Veterinary insecticide and ixodicide introduced by Upjohn Co. (later Nor-Am).
APPLICATIONS:
PRODUCTS:
Discontinued products Banol* (Upjohn).
ANALYSIS:
Residues by glc of a derivative (AOACMethods, 18th Ed., 975.40).
carbasulam
Herbicide
NOMENCLATURE:
Common name carbasulame ((m) F-ISO); carbasulam (BSI, E-ISO)
IUPACname methyl 4-(methoxycarbonylsulfamoyl)carbanilate
Chemical Abstracts name methyl [[4-[(methoxycarbonyl)amino]phenyl]
sulfonyl]carbamate CASRN[1773371] DevelopmentcodesM&B 9555
SmilescodeCOC(=O)Nc1ccc(cc1)S(=O)(=O)NC(=O)OC
COMMERCIALISATION:
History Herbicide evaluated by May & Baker Ltd (later Rhne-Poulenc Agrochimie).
carbon disulfide
Insecticide, nematicide
NOMENCLATURE:
Common name carbon disulfide (ESA); carbon disulphide (BSI, E-ISO, accepted in lieu of
common name); sulfure de carbone (F-ISO)
84 carbon disulfide
IUPACname carbon disulfide

Chemical Abstracts name carbon disulfide Other names carbon bisulphide
CASRN[75150] ECno2008436 SmilescodeS=C=S
PHYSICAL CHEMISTRY: Mol. wt. 76.13 M.f. CS2 Form Colourless mobile liquid.
Its impurities have an unpleasant odour. M.p.108.6C B.p. 46.3C V.p. 4.7 107 mPa
(25C) Kow logP = 1.84 (Agchem. Desk Ref.) S.g./density 1.2628 (20C); gas, 2.63 (air
= 1) Solubility In water 2.2 g/l (32C). Miscible with chloroform, diethyl ether, ethanol.
F.p.c.20C; ignites spontaneously >100C
COMMERCIALISATION:
History Used as insecticide in 1854 by Garreau (see Science, 1926, 64, 326).
APPLICATIONS:
ModeofactionFumigant insecticide and nematicide. Uses For fumigation of nursery
stock and for soil treatment against insects and nematodes. It was also used in some
countries as an insecticide in mixtures with carbon tetrachloride (to reduce fire hazard)
for fumigating stored grain.
PRODUCTS:
Discontinued products Weevil Tox* (Stauffer).
ANALYSIS:
Product analysis by glc (AOACMethods, 18th Ed., 966.05). Residues in grain may be
determined by glc (S. G. Heuser & K. A. Scudmore, J. Sci. Food Agric., 1969, 20, 566) or by
colorimetry of a derivative (C. L. Dunning, J. Assoc. Off. Agric. Chem., 1957, 40, 168). See also
Pestic. Anal. Man., II, 180.467. The concentration in air may be measured by drawing the air
through an ethanolic solution of diethylamine and copper(II) acetate and colorimetry of
the complex produced. Methods reviewed by J. L. Daft in Comp. Anal. Profiles,Chapter11.
EHC 10 (1979). JMPR Evaln. I 45 (1985); JMPR Evaln. 17 (1971). ICSC.022 (2000). CICAD 46
(2002). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Inhalation The vapour is highly poisonous, producing giddiness and vomiting in 30min at
6.8 mg/l air; repeated daily exposures to 0.227 mg/l air caused ill health.
NOEL Inhalation NOEL for rats 20 ppm (11 mg/kg b.w.) (EPA Tracking). ADI/RfD (JMPR)
No ADI [1965]; (EPA) RfD 0.1 mg/kg b.w. [1985]. Toxicity Class WHO (a.i.) FM
ECClassification F; R11| R62, R63| T; R48/23| Xi; R36/38 (concentration-dependent)
carbon tetrachloride
Insecticide
NOMENCLATURE:
Common name carbon tetrachloride (BSI, E-ISO, ESA, traditional name); t(trachlorure
de carbone) (F-ISO, accepted in lieu of a common name)
carbon tetrachloride 85
IUPACname carbon tetrachloride; tetrachloromethane

Chemical Abstracts name tetrachloromethane CASRN[56235]
ECno2002628 SmilescodeClC(Cl)(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 153.8 M.f. CCl4 Form Colourless liquid.
M.p.23C B.p. 76C V.p. 15 kPa (25C) Henry 8.24 103 Pa m3 mol1 (calc.) S.g./
density 1.588 (25C); gaseous, 5.32 (air = 1) Solubility In water 280 mg/kg (25C).
Miscible with most organic solvents. Stability Though generally inert, it is decomposed by
water at high temperatures.
F.p. Non-flammable and non-explosive
COMMERCIALISATION:
History Use as insecticidal fumigant described by W. E. Britton (Conn. Agric. Exp. Stn. Rep.,
1908, No. 31).
APPLICATIONS:
ModeofactionFumigant insecticide Uses Shows weak insecticidal activity, but was used
for grain disinfestation when long exposures are possible, its main advantages being low
absorption by treated grain. It was often used in mixtures with more potent fumigants,
such as ethylene dichloride, to reduce the fire hazard of the latter. It has also been used as
an anthelmintic in veterinary practice.
ANALYSIS:
Product analysis by glc (AOACMethods, 14th Ed., 6.1596.164). Residues in stored cereals
determined by glc with ECD (ibid., 18th Ed., 977.18; K. A. Scudamore, Anal. Methods Pestic.
Plant Growth Regul., 1988, 16, 207, 222; Anal. Methods Residues Pestic., 1988, Part I, M8; Analyst
(London), 1974, 99, 570). Methods reviewed by J L Daft in Comp. Anal. Profiles,Chapter11.
EHC 208 (1999). JMPR Evaln. I 45 (1985); JMPR Evaln. 33 (1979). HSG 108 (1998). ICSC.024
(2000). IARC 20 (1979); 71 (1999).
IARC Class 2B
Oral Acute oral LD50 for rats 57309770, mice 12800, rabbits 63809975 mg/kg.
Skin and eye Acute percutaneous LD50 for rats 5070 mg/kg (ESA, Special
Publication,1978). NOEL NOAEL for rats 0.71 mg/kg b.w. daily (EPA IRIS).
ADI/RfD (JMPR) No ADI [1965]; (EPA) cRfD 0.0007 mg/kg b.w. [1991]. Other It is a
general anaesthetic, prolonged exposure causing irritation of the mucous membranes,
headache and nausea; repeated exposure to high concentrations causes liver damage.
ECClassification R40| T; R23/24/25, R48/23| R52, R53| N; R59| concn. dep.
86 carbon tetrachloride
carbophenothion
S OCH CH
2 3
Cl S CH2 S P
OCH2CH3
IRAC1B
NOMENCLATURE:
Common name carbophenothion (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate
Chemical Abstracts name S-[[(4-chlorophenyl)thio]methyl] O,O-
diethyl phosphorodithioate CASRN[786196] ECno2123241
DevelopmentcodesR-1303 (Stauffer) SmilescodeCCOP(=S)(OCC)SCSc1ccc(Cl)cc1
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 342.9 M.f. C11H16ClO2PS3 Form Colourless liquid
with a mercaptan-like odour; (tech. is a pale amber liquid). B.p. 82C /0.01 mmHg V.p.
1.07 mPa (25C)
Kow logP = 4.75 (Agchem. Desk Ref.) S.g./density 1.271 (25C); 1.285 (20C, tech.)
Solubility In water <1 mg/l (room temperature). Miscible with most organic solvents,
e.g. alcohols, esters, ketones, xylene, mineral oils. Miscible with vegetable oils. Stability
Thermally stable up to 80C. Relatively stable to hydrolysis, particularly in alkaline media.
COMMERCIALISATION:
History Insecticide and acaricide (Agric. Chem., 1956, 11(11), 91). Introduced by Stauffer
Chemical Co. (later ICI Americas). Patents US 2793224
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic insecticide and
acaricide with contact and stomach action. Long residual activity. Uses Control of aphids
and spider mites on citrus fruit and cotton; and spider mites, aphids, suckers, Lepidoptera,
and other insect pests in fruit, nut crops, vines, olives, figs, vegetables, beet, maize, sorghum,
clover, alfalfa, cucurbits, soya beans, ornamentals, turf, and other crops. Used as a seed
treatment for control of wheat bulb flies in wheat. Used in combination with petroleum
oil for control of overwintering aphids, scale insects, and mites on dormant deciduous
fruit trees. Also used as an animal ectoparasiticide. Phytotoxicity Slightly phytotoxic. Leaf
damage may occur on susceptible apples (Delicious), and on roses under glass, especially
under warm, moist conditions. Grapefruits, kumquats, citrons, and some varieties of grape
may also suffer injury. Formulation types EC; WP; GR; DP; Seed treatment.
PRODUCTS:
Discontinued products Trithion* (Stauffer).
carbophenothion 87
ANALYSIS:
Product by glc with FID (Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 519521).
Residues by glc with TID or FPD (AOACMethods, 18th Ed., 974.22, 968.24; J. A. Burke J.
Assoc. Off. Anal. Chem. 1965, 48, 10371058; Anal. Methods Pestic. Plant Growth Regul. 1972, 6,
521528; D. C. Abbott et al., Pestic. Sci., 1970, 1, 10).
EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Evaln. 41
(1983). ICSC.410 (1997). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD50 for male rats 79.4, female rats 20, mice 218 mg/kg.
Skin and eye Acute percutaneous LD50 for rabbits 1850, male rats 54, female rats 27 mg/
kg. NOEL LOEL (2 y) for dogs 5 ppm (0.125 mg/kg b.w.) (EPA Tracking). ADI/RfD (JMPR)
0.0005 mg/kg b.w. [1980]; (EPA) 0.00013 mg/kg b.w. [1987]. Toxicity Class WHO (a.i.) Ib
EPA (formulation) I ECClassification T; R24/25| N; R50, R53
ECOTOXICOLOGY:
Fish Very toxic to fish. Bees Moderately toxic to bees.
ENVIRONMENTAL FATE:
Animals Readily degraded in rats, primarily to water soluble products which are
excreted in the urine (FAO/WHO 28). Plants On leaf surfaces, oxidation occurs to the
phosphorothioate (B. J. Luberoff et al., Agric. Chem., 1958, 13(3), 83).
Soil/Environment Undergoes oxidation to the sulfone, sulfoxide, thiol, thiosulfone, and
thiosulfoxide, presumably combined with dealkylation and hydrolysis.
carboxazole
Herbicide
NOMENCLATURE:
Common name carboxazole (BSI, E-ISO, (m) F-ISO)
IUPACname methyl 5-tert-butyl-1,2-oxazol-3-ylcarbamate; methyl 5-tert-butylisoxazol-
3-ylcarbamate
Chemical Abstracts name methyl [5-(1,1-dimethylethyl)-3-isoxazolyl]carbamate
CASRN[55808134] DevelopmentcodesSSH-42
SmilescodeCOC(=O)Nc1cc(on1)C(C)(C)C
COMMERCIALISATION:
History Herbicide evaluated by Shionogi & Co. Ltd.
88 carboxazole
CECA
Fungicide
NOMENCLATURE:
Common name CECA (JMAF)
IUPACname 2-chloro-N-(2-cyanoethyl)acetamide (I)
Chemical Abstracts name (I) CASRN[17756819] DevelopmentcodesNF 21
SmilescodeClCC(=O)NCCC#N
PHYSICAL CHEMISTRY: Mol. wt. 146.6 M.f. C5H7ClN2O
COMMERCIALISATION:
History Fungicide introduced by Nippon Soda Co., Ltd.
PRODUCTS:
Discontinued products Udonkor* (Nippon Soda).
CGA 80 000
Fungicide
NOMENCLATURE:
IUPACname (RS)--[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]--butyrolactone
Chemical Abstracts name ()-N-(3-chloro-2,6-dimethylphenyl)-2-methoxy-N-
(tetrahydr-2-oxo-3-furanyl)acetamide CASRN[79555809] racemate; [67932858]
unstated stereochemistry DevelopmentcodesCGA 80 000
SmilescodeCOCC(=O)N(C1CCOC1=O)c2c(C)ccc(Cl)c2C
PHYSICAL CHEMISTRY: Mol. wt. 311.8 M.f. C15H18ClNO4 M.p.94.9C V.p. 5 104
mPa (20C) Kow logP = 1.5 (unspecified organic phase, reversed-phase tlc) Henry 2.29
107 Pa m3 mol1 (calc.) Solubility In water 680 mg/l (20C). Stability Stable to hydrolysis
at pH 1 to 5; DT50 154d (pH 7), 19 d (pH 8) (20C).
COMMERCIALISATION:
History Fungicide reported by P. Margot etal. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 2,
527). Evaluated by Ciba-Geigy AG.
APPLICATIONS:
ModeofactionSystemic fungicide. Uses Control of soil-borne late blight and root rot
on tobacco, citrus, avocado, carrots, soft fruit, and ornamentals. Formulation types GR;
SC.
PRODUCTS:
Discontinued products Vangard* (Cyanamid).
>2000 mg/kg. Not a skin or eye irritant. Marginal skin sensitiser (guinea-pigs).
Inhalation LC50 (4 h) >1.7 mg/l air.
CGA 80 000 89
ECOTOXICOLOGY:
Fish Non-toxic. Bees Non-toxic.
chinomethionat
IRACUN
N S
O
CH3 N S
NOMENCLATURE:
Common name chinomethionat (E-ISO); no name (USA); quinoxalines (JMAF);
chinom(thionate) ((m) F-ISO); quinomethionate (BSI); oxythioquinox (Australia, ESA)
IUPACname S,S-(6-methylquinoxaline-2,3-diyl) dithiocarbonate; 6-methyl-1,3-
dithiolo[4,5-b]quinoxalin-2-one
Chemical Abstracts name 6-methyl-1,3-dithiolo[4,5-b]quinoxalin-2-one
CASRN[2439012] ECno2194553 DevelopmentcodesBayer 36 205;
Bayer SAS 2074 Official codes ENT 25 606 SmilescodeCc1ccc2nc3sc(=O)sc3nc2c1
PHYSICAL CHEMISTRY: Mol. wt. 234.3 M.f. C10H6N2OS2 Form Yellow crystals.
M.p.170C V.p. 0.026 mPa (20C) Kow logP = 3.78 (20C) Henry 6.09 103 Pa m3
mol1 (calc.) S.g./density 1.556 (20C) Solubility In water 1 mg/l (20C). In toluene 25,
dichloromethane 40, hexane 1.8, isopropanol 0.9, cyclohexanone 18, DMF 10, petroleum
oils 4 (all in g/l, 20C). Soluble in hot benzene and dioxane. Stability Relatively stable
under normal conditions. Hydrolysed in alkaline media; DT50 (22C) 10 d (pH 4), 80 h (pH
7), 225 min (pH 9).
COMMERCIALISATION:
History Acaricide and fungicide reported by K. Sasse (Hoefchen-Briefe (Engl. Ed.), 1960,
13, 197; K. Sasse et al., Angew. Chem., 1960, 72, 973). Introduced by Bayer AG. Patents DE
1100372; BE 580478
APPLICATIONS:
ModeofactionSelective non-systemic contact fungicide with protective and eradicant
action. Uses Control of powdery mildews and spider mites on fruit (including citrus),
ornamentals, cucurbits, cotton, coffee, tea, tobacco, walnuts, vegetables, and glasshouse
crops; and American gooseberry mildew on gooseberries and currants.
Phytotoxicity Phytotoxic to certain varieties of apple, pear, currant, rose, and
ornamentals. Formulation types DP; FU; SC. WP. Compatibility Incompatible with
mineral oils (phytotoxicity may result), and with formulations based on thiram.
90 chinomethionat
PRODUCTS:
Discontinued products Morestan* (Bayer CropScience);
Discontinuedmixtures Morestan VP* (+dichlorvos) (Nippon Soda).
ANALYSIS:
Product analysis by hplc (CIPACHandbook, 1985, 1C, 2019; AOACMethods, 18th Ed., 986.08)
or by uv spectrometry (details available from Bayer CropScience). Residues determined
by glc (Man. Pestic. Residue Anal., p. 13; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64,
733; R. T. Krause & E. M. August, ibid., 1983, 66, 1018), or by colorimetry after conversion
to a derivative (H. Tietz et al., ibid., 1962, 15, 166; C. A. Anderson, Anal. Methods Pestic., Plant
Growth Regul. Food Addit., 1967, 5, 277). See also Pestic. Anal. Man., I, 302; ibid., II 180.338.
Methods for the determination of residues are also available from Bayer CropScience.
JMPR Evaln. 43 (1984); JMPR Evaln. II 52 (1987). EU Status (1107/2009) Not approved,
percutaneous LD50 for rats >5000 mg/kg. Slightly irritating to skin; severely irritating to
eyes (rabbits). Inhalation LC50 (4 h) for male rats >4.7, female rats 2.2 mg/l (dust).
NOEL (2 y) for rats 40, male mice 270, female mice <90 mg/kg diet; (1 y) for dogs 25 mg/
kg diet (0.625 mg/kg b.w.). ADI/RfD (JMPR) 0.006 mg/kg b.w. [1987]; (EPA) 0.006 mg/kg
b.w. [1999]. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification R62|
Xn; R20/21/22, R48/22| Xi; R36| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 196 mg/kg. Dietary LC50 (5 d) for bobwhite quail
2409, mallard ducks >5000 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.0334, rainbow
trout 0.131, golden orfe 0.24 mg/l. Daphnia LC50 (48 h) 0.12 mg/l. Algae ErC50 (96 h) for
Scenedesmus 0.14 mg/l. Bees Not toxic to bees; LD50 >100 g/bee. Worms LC50 (14 d)
>1000 mg/kg.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, chinomethionat is rapidly metabolised,
andc.90% is eliminated within 3 days in the faeces and urine. The main metabolite
is chinomethionat acid (dimethylmercaptoquinoxaline-6-carboxylic acid), which also
occurs in the conjugated form. Plants After application to fruit, no penetration of the
a.i. or metabolites in the fruit pulp was observed. The only metabolite detected was
dihydromethylquinoxalinedithiol. Soil/Environment Koc 4590 (3 soil types from sandy
loam to high organic matter). DT50 in standard soil land 2 13 d.
chinomethionat 91
chlobenthiazone
Fungicide
O
S
CH3 N
Cl
NOMENCLATURE:
Common name chlobenthiazone (BSI, E-ISO, (f) F-ISO)
IUPACname 4-chloro-3-methyl-1,3-benzothiazol-2(3H)-one; 4-chloro-3-
methylbenzothiazol-2(3H)-one Chemical Abstracts name 4-chloro-3-methyl-
2(3H)-benzothiazolone CASRN[63755055] DevelopmentcodesS-1901
SmilescodeCn1c(=O)sc2cccc(Cl)c12
PHYSICAL CHEMISTRY: Mol. wt. 199.7 M.f. C8H6ClNOS Form Colourless crystals.
M.p.131132C
V.p. 172 mPa (20C) Henryc.7.47 101 Pa m3 mol1 (calc.) Solubility In water 46mg/
kg (21.5C). In acetone, methanol, xylene 330, chloroform, cyclohexanone 500, ethyl
acetate 200 (all in g/kg, 21.5C). Stability Stable in aqueous acid and alkali.
COMMERCIALISATION:
History Fungicide reported by S. Inoue etal. (Proc. 1981 Br. Crop. Prot. Conf. - Pests Dis.,
1981, 1, 19). Evaluated by Sumitomo Chemical Co., Ltd.
APPLICATIONS:
ModeofactionSystemic fungicide. It inhibits the development of infection pegs from
appressoria. Uses Submerged applications of granules (2.43.2 kg/ha) or foliar applications
of a dust are effective in controlling Pyricularia oryzae in rice. Formulation types DP; GR .
1250 mg/kg. Skin and eye Acute percutaneous LD50 for rats and mice >2500 mg/kg. Not
irritant to the abraded skin of rabbits; minimally irritant to their eyes. NOEL In 0.5 y
feeding trials, rats receiving 100 mg/kg diet showed no ill-effect.
chlomethoxyfen
Herbicide
HRACE WSSA 14; diphenyl ether
OCH3
Cl O NO2
Cl
92 chlomethoxyfen
NOMENCLATURE:
Common name chlom(thoxyf) ((m) F-ISO); chlormethoxynil (JMAF); chlomethoxyfen
(BSI, E-ISO) IUPACname 5-(2,4-dichlorophenoxy)-2-nitroanisole
Chemical Abstracts name 4-(2,4-dichlorophenoxy)-2-methoxy-1-nitrobenzene;
2,4-dichloro-1-(3-methoxy-4-nitrophenoxy)benzene CASRN[32861851]
DevelopmentcodesX-52 SmilescodeCOc1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 314.1 M.f. C13H9Cl2NO4 Form Yellow crystals.
M.p.113114C B.p. 260C /25 mmHg V.p. 1.87 mPa (25C) Kow logP = 3.34 (20C)
S.g./density 1.37
Solubility In water 0.3 mg/l (15C). In acetone 200, DMSO 100, benzene 150 (all in g/kg,
15C). Stability Stable to acids, alkalis, and light.
COMMERCIALISATION:
History Introduced as a herbicide by Nihon Nohyaku Co., Ltd. Patents JP 600441
Manufacturers Ishihara Sangyo
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionSelective contact
herbicide, absorbed by the leaves and stems. Uses Pre-emergence control of Scirpus
spp., Echinochloa crus-galli, and other annual weeds in transplanted rice at 1.52.5 kg/ha.
Phytotoxicity May scorch old leaves. Formulation types WP; GR .
PRODUCTS:
Discontinued products Condore* (Ishihara Sangyo); Difenex* (Ishihara Sangyo);
Diphenex* (Ishihara Sangyo); Ekkusugoni* (Ishihara Sangyo, Nihon Nohyaku); Ikkokuso*
(Ishihara Sangyo).
ANALYSIS:
Product analysis by glc with FID (F.Yamane & K. Tsuchiya, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 267). Residues determined by glc with ECD (idem, ibid.).
Oral Acute oral LD50 for rats and mice >10000 mg/kg. Skin and eye Acute percutaneous
LD50 for rats >5000 mg/kg. Inhalation LC50 for rats >1.767 mg/l. Toxicity Class WHO
(a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 11.2 mg/l. Daphnia LC50 (24 h) >47.5 mg/l.
ENVIRONMENTAL FATE:
Animals Metabolised in rats to form glucurone and glutathione conjugates.
Soil/Environment In soil, DT50 743 d. Kd 5251407.
chlomethoxyfen 93
chloramben
Herbicide
CO2H
Cl
Cl NH2
HRACO WSSA 4; benzoic acid (auxin)

NOMENCLATURE:
Common name chloramben (BSI, E-ISO, ANSI, WSSA); amben* (former WSSA name);
chloramb(n) ((m) F-ISO)
IUPACname 3-amino-2,5-dichlorobenzoic acid
Chemical Abstracts name 3-amino-2,5-dichlorobenzoic acid CASRN[133904]
DevelopmentcodesACP M-629 (Amchem) SmilescodeNc1cc(Cl)cc(C(=O)O)c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 206.0 M.f. C7H5Cl2NO2 Form Colourless crystals.
M.p.200201C
V.p. 930 mPa (100C) Solubility In water 700 mg/l (25C). In DMF 1206, acetone,
methanol 223, ethanol 173, isopropanol 113, diethyl ether 70, chloroform 0.9, benzene
0.2 (all in g/kg, room temperature). Insoluble in carbon tetrachloride. Stability Thermally
stable up to the boiling point. Stable to oxidising agents, acids and alkalis. Decomposed by
sodium hypochlorite solutions. Sensitive to light. pKa 3.40 (ACS Adv. in Chem. Series no. 111,
cited in ARS PPD).
COMMERCIALISATION:
History Herbicide introduced by Amchem Products, Inc. (later Bayer AG). Patents US
3014063; US 3174842
APPLICATIONS:
Biochemistry Synthetic auxin (acting like indolylacetic acid). The N-glycoside was
isolated from soya beans in amounts equivalent to the chloramben applied, but little
was recovered from barley, a susceptible crop (S. R. Colby, Science, 1965, 150, 619).
ModeofactionSelective systemic herbicide, absorbed by the seeds and roots, with
limited translocation. Inhibits root development of seedling weeds. Uses Used pre-planting
incorporated and pre-emergence, at 24 kg/ha, to control grasses and broad-leaved weeds
in seedling asparagus, navy beans, peanuts, maize, sweet potatoes, pumpkins, soya beans,
squash, sunflowers and certain ornamentals. Formulation types DS; GR; SL; SP.
PRODUCTS:
Discontinued products Amiben* (ammonium salt) (Aventis).
ANALYSIS:
Product analysis by uv spectrophotometry (AOACMethods, 18th Ed., 971.06;
CIPACHandbook, 1983, 1B, 1747) or volumetric methods. See also: H. S. Segal & M. L.
94 chloramben
Sutherland, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 321; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 588. Residue analysis by glc of methyl ester.
rats >3160 mg/kg. Mild skin and eye irritant (rabbits). NOEL (2 y) for rats 10000 mg/kg
diet. ADI/RfD (EPA) cRfD 0.015 mg/kg b.w. [1988]. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks 4640 mg/kg. Fish Not toxic to fish. Bees Not
toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, the major metabolites were 3-amino-5-chlorobenzoic acid,
3-aminobenzoic acid, 2,5-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid and
2,5-dichloroaniline. Plants In plants, chloramben is converted to a highly stable
N-glucoside, which retards further degradation. Soil/Environment Undergoes microbial
degradation in soil. Duration of activity isc.68 w.
chloraniformethan
Fungicide
NOMENCLATURE:
Common name chloraniformethan (BSI, E-ISO); chloraniform(thane) ((m) F-ISO)
IUPACname N-[2,2,2-trichloro-1-(3,4-dichloroanilino)ethyl]formamide
Chemical Abstracts name N-[2,2,2-trichloro-1-[(3,4-dichlorophenyl)amino]
ethyl]formamide CASRN[20856579] DevelopmentcodesBayer 79 770
SmilescodeClc1ccc(NC(NC=O)C(Cl)(Cl)Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 336.4 M.f. C9H7Cl5N2O M.p.134136C V.p. <1
mPa (20C);c.1.3 mPa (40C) Henry <2 103 Pa m3 mol1 (20C, calc.) Solubility In
water 0.016 g/100 ml (20C). In methanol 40, methyl isobutyl ketone 40.2, cyclohexanone
45, DMF 55, toluene 1.33, n-heptane 0.008 (all in g/100 g, 20C). Stability Converted by
strong acids and alkalis to 3,4-dichloroaniline.
COMMERCIALISATION:
History Fungicide reported by A. O. Paulus etal. (Calif. Agric., 1968, 22(3), 10). Introduced
by Bayer AG.
APPLICATIONS:
ModeofactionFungicide with curative action. Uses Control of mildew, especially
Erysiphe species, in cereals and ornamentals (roses, chrysanthemums, begonias).
chloraniformethan 95
PRODUCTS:
Discontinued products Imugan* (Bayer); Milfaron* (Bayer).
ANALYSIS:
Product by gc determination, as for residues (R. A. Hoodless & M. Sargent Analyst 1976,
101, 161166). residues by extraction of plant material by maceration with acetone,
clean-up, hydrolysis with sulfuric acid, steam distillation of the resultant 3, 4-dichloroaniline
from alkaline solution, diazotization, coupling with N-(1-naphthyl)ethylenediamine, and
colorimetric determination at 530 nm (K.Vogeler Pflanz.-Nachr. Bayer 1969, 22, 299304
and Man. Pestic. Residue Anal., 271).
Oral Acute oral LD50 for male rats >2500, female mice >1000, cats >500, guinea pigs
250500 mg/kg. Skin and eye Acute percutaneous LD50 for rats >500 mg/kg. 14 d activity
on the skin of rabbits has no detrimental effects on general condition, organs, etc.
NOEL Feeding of 10, 30, and 100 mg/kg b.w. for 14 w does not cause any symptoms of
toxicity; intake of 100 mg/kg produces liver hypertrophy. Toxicity Class WHO (a.i.) O
ECOTOXICOLOGY:
Fish LC50 for goldfish 110 mg/l.
Details PM4, p. 91.
chloranil
Fungicide
NOMENCLATURE:
Common name chloranil (BSI, E-ISO); chloranile (F-ISO); traditional names accepted in
lieu of a common name
IUPACname tetrachloro-p-benzoquinone; 2,3,5,6-tetrachloro-1,4-benzoquinone
Chemical Abstracts name 2,3,5,6-tetrachloro-2,5-cyclohexadiene-1,4-dione
CASRN[118752] ECno2042744 SmilescodeClC1=C(Cl)C(=O)C(=C(Cl)
C1=O)Cl
PHYSICAL CHEMISTRY: Mol. wt. 245.9 M.f. C6Cl4O2 M.p.292C (in closed tube)
V.p. 1300 mPa (70.7C)
S.g./density 1.97 Solubility Practically insoluble in water. In acetone 33, ether 16, DMF
5.4, solvent naphtha 5.4, benzene 1.3, methanolc.0.1, carbon tetrachloridec.0.1, dibutyl
phthalatec.0.1 (all in g/100 g). Stability Stable in closed containers. Slowly decomposed by
sunlight. Decomposed by alkalis; stable in acidic media.
COMMERCIALISATION:
History Fungicidal activity of chloranil, long known as a chemical reagent, reported by
H. S. Cunningham & E. G. Shavelle (Phytopathology, 1940, 30, 4). Introduced by Uniroyal
Chemical Co., Inc.
96 chloranil
APPLICATIONS:
ModeofactionFungicide and seed protectant with secondary insect repellent and
bactericidal effects. Uses Used particularly on vegetable and ornamental seeds. Active
against damping-off on beans. Formulation types WP; DP; DS .
PRODUCTS:
Discontinued products Spergon* (Uniroyal).
ANALYSIS:
Product by reduction of chloranil with potassium iodide and potentiometric titration of
the liberated iodine with sodium thiosulfate (Anal. Methods Pestic. Plant Growth Regul., 3, 29),
or total chlorine determination by the Stepanov method or Parr bomb decomposition.
Residues by extraction with benzene, clean-up, reaction with diphenyl-p-phenylenediamine
to give a blue colour, transfer of the dye into the aqueous-acid phase, and determination by
spectrophotometry at 700 nm (Anal. Methods Pestic. Plant Growth Regul., 3, 32).
Oral Acute oral LD50 for ratc.4 g/kg. Skin and eye Slight absorption through the skin;
nevertheless there is local irritation. NOEL Long-term feeding as 0.5% of diet causes no
damage to health. Other I.p. LD50c.0.5 g/kg. Toxicity Class WHO (a.i.) O
ECClassification Xi; R36/38| N; R50, R53
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Soil/Environment In plants, the chlorine atoms are replaced by sulfhydryl groups. In
solution, under the influence of sunlight, reduction to tetrachlorohydroquinone followed by
replacement of chlorine atoms with hydroxy groups.
Details PM5, p. 90.
chloranocryl
Herbicide
NOMENCLATURE:
Common name chloranocryl (BSI, E-ISO, (m) F-ISO); dicryl (Canada, WSSA, ex ANSI)
IUPACname 3,4-dichloro-2-methylacrylanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)-2-methyl-2-propenamide
CASRN[2164092] DevelopmentcodesFMC 4556
SmilescodeCC(=C)C(=O)Nc1ccc(Cl)c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 230.1 M.f. C10H9Cl2NO
COMMERCIALISATION:
History Herbicide reported by S. W. Bingham & W. K. Porter (Weeds, 1961, 9, 282).
Introduced by FMC Corp.
chloranocryl 97
APPLICATIONS:
ModeofactionContact herbicide.
PRODUCTS:
Discontinued products Dicryl* (FMC).
Details PM2, p. 85.
chlorazifop; chlorazifop-propargyl
Herbicide
NOMENCLATURE:
Common name chlorazifop (BSI, E-ISO, (m) F-ISO)
IUPACname ()-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]
propanoic acid CASRN[60074251] chlorazifop, unstated stereochemistry;
[74310706] chlorazifop, racemate; [72492547] chlorazifop, (R)- isomer;
[72492558] chlorazifop, (S)- isomer; [72280525] chlorazifop-propargyl,
unstated stereochemistry, formerly [77107494]; [74267699] chlorazifop-
propargyl, (R)- isomer DevelopmentcodesCGA 82 725 (chlorazifop-propargyl)
Smilescodechlorazifop:CC(Oc1ccc(Oc2ncc(Cl)cc2Cl)cc1)C(=O)O
PHYSICAL CHEMISTRY: Mol. wt. 328.2; (propargyl ester 366.2) M.f. C14H11Cl2NO4;
(propargyl ester C17H13Cl2NO4)
COMMERCIALISATION:
History Chlorazifop-propargyl evaluated as a herbicide by Ciba-Geigy AG (chlorazifop
also formed by hydrolysis of isoxapyrifop in vivo).
chlorazine
Herbicide
NOMENCLATURE:
Common name chlorazine (BSI, WSSA, ex ANSI)
IUPACname 6-chloro-N2,N2,N4,N4-tetraethyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N,N,N,N-tetraethyl-1,3,5-triazine-2,4-diamine
CASRN[580483] DevelopmentcodesG 25 804
SmilescodeCCN(CC)c1nc(Cl)nc(n1)N(CC)CC
PHYSICAL CHEMISTRY: Mol. wt. 257.8 M.f. C11H20ClN5
COMMERCIALISATION:
History Herbicide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
98 chlorazine
chlorbenside
Acaricide
NOMENCLATURE:
Common name chlorbenside (BSI, E-ISO, F-ISO, ESA, ex ANSI)
IUPACname 4-chlorobenzyl 4-chlorophenyl sulfide
Chemical Abstracts name 1-chloro-4-[[(4-chlorophenyl)methyl]thio]
benzene CASRN[103173] DevelopmentcodesHRS 860; RD 2195
SmilescodeClc1ccc(CSc2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 269.2 M.f. C13H10Cl2S M.p.72.5C B.p. 8384C
/0.003 mbar V.p. 1.6 mPa (30C) Solubility In water <1:5000. In alcohol 2.8%; readily
soluble in acetone and benzene. Stability Extremely stable to acids and alkalis. Oxidising
agents convert it to the sulfoxide and sulfone.
COMMERCIALISATION:
History Acaricide reported by J. E. Cranham etal. (Chem. Ind. (London), 1953, p. 1206)
and by D. J. Higgons & D. W. Kilbey (ibid., p. 1359). Introduced by The Boots Co., Ltd (later
Schering Agrochemicals).
APPLICATIONS:
ModeofactionSpecific acaricide, with ovicidal and larvicidal properties. Little insecticidal
activity. Uses Control of most varieties of spider mites (weak activity against adults),
particularly in the pre-blossom stage in fruit cultivation and on ornamentals and nursery
stock. Phytotoxicity Cucumbers and other cucurbits are susceptible. Formulation
types WP; EC.
PRODUCTS:
Discontinued products Chlorparacide* (Boots); Chlorsulphacide* (Boots); Redon*
(Sariaf).
ANALYSIS:
Product by extraction with ether, hydrolysis to p-chlorophenol, steam distillation,
colorimetric determination at 510 nm after colour reaction with 4-aminoantipyrine in the
presence of potassium ferricyanide (Anal. Insectic. Acar.). Residues by extraction from plants
with benzene, oxidation to the sulfone, nitration, colour reaction with sodium methylate,
and colorimetric determination (J. T. Martin & R. F. Batt Annu. Rep. Long Ashton Res. Stat.
1955, 106110, partly by the method of H. Niessen & H. Frehse Gadamer 1969). For a
further colorimetric method see H. J. Hardon etal. (J. Sci. Food Agric. 1957, 8, 368370).
JMPR Evaln. 4 (1965). EU Status (1107/2009) Never notified to the EU.
Oral Acute oral LD50 for rats >10000 mg/kg. Skin and eye Slight irritant action on skin
and eyes. NOEL A 5 mg/kg concentration can be tolerated for 3 w in the diet of dogs.
ADI/RfD (JMPR) 0.01 mg/kg b.w. [1965]. Toxicity Class WHO (a.i.) O
chlorbenside 99
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Animals In warm-blooded organisms, elimination is as the glucuronic acid conjugate.
Soil/Environment Presumably degraded by enzymic hydrolysis.
Details PM3, p. 97.
chlorbicyclen
Insecticide
NOMENCLATURE:
Common name chlorbicyclen (BSI, E-ISO); chlorbicycl(ne) ((m) F-ISO)
IUPACname 1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)-8,9,10-trinorborn-2-ene
Chemical Abstracts name 1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)
bicyclo[2.2.1]hept-2-ene CASRN[2550756] DevelopmentcodesHercules 426
SmilescodeClCC1C(CCl)C2(Cl)C(=C(Cl)C1(Cl)C2(Cl)Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 397.8 M.f. C9H6Cl8
COMMERCIALISATION:
History Insecticide introduced by Hercules Inc. Agrochemicals (and later Nor-Am).
PRODUCTS:
Discontinued products Alodan* (Hercules).
chlorbromuron
Herbicide
HRACC2 WSSA 7 CH3
O
C NOCH3
Br NH
Cl
NOMENCLATURE:
Common name chlorobromuron ((m) F-ISO); chlorbromuron (BSI, E-ISO, WSSA, ex-ANSI)
IUPACname 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea
Chemical Abstracts name N-(4-bromo-3-chlorophenyl)-N-methoxy-N-methylurea
CASRN[13360457] ECno2364119 DevelopmentcodesC 6313 (Ciba)
100 chlorbromuron
SmilescodeCON(C)C(=O)Nc1ccc(Br)c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 293.5 M.f. C9H10BrClN2O2 Form Colourless
powder. M.p.9597C
V.p. 0.053 mPa (20C) Kow logP = 2.9 Henry 4 104 Pa m3 mol1 (calc.)
S.g./density 1.69 (20C) Solubility In water 35 mg/l (20C). In acetone 460,
dichloromethane 170, hexane 89, benzene 72, isopropanol 12 (all in g/kg, 20C).
Stability Slowly hydrolysed in neutral, slightly acidic, and slightly alkaline media.
COMMERCIALISATION:
History Herbicide reported by D. H. Green etal. (Proc. Br.Weed Control Conf., 8th, 1966, 2,
363). Introduced by Ciba AG (later Syngenta AG). Patents BE 662268; GB 965313
APPLICATIONS:
receptor site. ModeofactionSelective herbicide, absorbed by the roots and leaves.
Uses Herbicide suitable for: pre-emergence use on carrots, peas, potatoes, soya beans,
and sunflowers, at 1.02.5 kg/ha; post-emergence use on carrots and transplanted celery,
at 0.751.5 kg/ha. Phytotoxicity A number of crops may be injured by pre-emergence
applications, e.g. rice, beet, okra, flax, cucurbits, tomatoes, strawberries, etc. Formulation
types WP.
PRODUCTS:
Discontinued products Maloran* (Syngenta).
ANALYSIS:
Product analysis by glc. Residues determined by hydrolysis to 4-bromo-3-chloroaniline,
a derivative of which is determined by colorimetry, or by glc with ECD (G.Voss, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 569).
Oral Acute oral LD50 for rats >5000 mg tech./kg. Skin and eye Acute percutaneous LD50
for rats >2000, rabbits >10000 mg/kg. Not a skin or eye irritant. Inhalation LC50 (6 h) for
rats >1.05 mg/l air. NOEL (90 d) for rats 316 mg/kg diet (21.0 mg/kg daily), dogs >316 mg/
kg diet (10.5 mg/kg daily). Toxicity Class WHO (a.i.) III (company classification); WHO
Recommended Classification gave U (now O) EPA (formulation) IV
ECOTOXICOLOGY:
Birds Dietary LC50 (10 d) for pheasants and mallard ducks >10250 mg/kg diet. Fish LC50
(96 h) for rainbow trout 5, bluegill sunfish 5, crucian carp 8 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, metabolism involves demethylation and deamination-decarboxylation to
the corresponding aniline molecule. Soil/Environment In biologically active soils, DT50
828 w; strongly bound to soil (Koc 908), indicating low leaching potential. In water, stable
against abiotic degradation, but in biologically active systems, DT50 411 w.
chlorbromuron 101
chlorbufam
Herbicide O
NH C CH3
O CH C CH
Cl
NOMENCLATURE:
Common name chlorbufame ((m) F-ISO); chlorbufam (BSI, E-ISO); BIPC (JMAF)
IUPACname 1-methylprop-2-ynyl 3-chlorocarbanilate; 1-methylprop-2-ynyl
3-chlorophenylcarbamate
Chemical Abstracts name 1-methyl-2-propynyl (3-chlorophenyl)carbamate
CASRN[1967164] SmilescodeCC(OC(=O)Nc1cccc(Cl)c1)C#C
PHYSICAL CHEMISTRY: Mol. wt. 223.7 M.f. C11H10ClNO2 Form Colourless crystals.
M.p.4546C
V.p. 2.1 mPa (20C) Henry 8.70 104 Pa m3 mol1 (calc.) S.g./density 1.22 (tech.)
Solubility In water 540 mg/l (20C). In methanol 286, acetone 280, ethanol 95 (all in g/kg,
20C). Stability Unstable in strongly acidic and alkaline media (l>pH>13). Changes colour
when exposed to light. Alcohols may cause trans-esterification. Stable up to 40C.
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Z. Pflanzenkr. Pflanzenpathol. Pflanzenschutz,
1960, 67, 577). Introduced by BASF AG. Patents DE 1034912; DE 1062482
Manufacturers BASF
APPLICATIONS:
Biochemistry Inhibits photosynthesis. Cell division inhibitor Uses Was normally used in
combination with other herbicides for pre-emergence control of grasses and broad-leaved
weeds in onions, leeks, garlic, shallots, carrots, beet, spinach, sunflowers, and bulb flowers.
Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products BiPC* (BASF); Discontinuedmixtures Alipur* (+cycluron)
(BASF).
ANALYSIS:
Product analysis by acid hydrolysis to 3-chloroaniline, determined by titration. Residues
determined by hydrolysis and colorimetry of the resulting 3-chloroaniline or by glc (Analyt.
von Pfl. in Wasser, p. 67)
Oral Acute oral LD50 for rats 2500 mg/kg. Skin and eye Mild skin irritant (rabbits).
NOEL (4 mo) for rats 400 mg/kg diet. Other Acute i.p. LD50 for mice 250 mg/kg.
102 chlorbufam

ECOTOXICOLOGY:
chlordecone
Insecticide
NOMENCLATURE:
Common name chlordecone (BSI, E-ISO, (m) F-ISO)
IUPACname perchloropentacyclo[5.3.0.02,6.03,9.04,8]decan-5-one
Chemical Abstracts name 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-
metheno-2H-cyclobuta[cd]pentalen-2-one CASRN[143500] ECno2056013
DevelopmentcodesGC-1189
SmilescodeClC1(C2(Cl)C3(Cl)C14Cl)C5(Cl)C(=O)C4(Cl)C(Cl)(C25Cl)C3(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 490.6 M.f. C10Cl10O M.p.Decomposes (without
melting) around 350C
V.p. 4 102 mPa (25C) Stability Wide stability to alkalis. Decomposed by strong
mineral acids.
COMMERCIALISATION:
History Insecticide introduced by Allied Chemical Corp., Agricultural Div. (later Hopkins
Ltd).
APPLICATIONS:
Biochemistry Interferes with oxidative phosphorylation. ModeofactionInsecticide
with stomach action and weak contact action. Secondary fungicidal effects. Uses
Insecticidal control of cockroaches and ants. Formulation types RB; WP.
PRODUCTS:
Discontinued products Kepone* (Hopkins).
ANALYSIS:
Product by gc determination as for residues, or by i.r. spectrophotometric determination
(6.1 m and 2.83.1 m) according to E. E. Gilbert etal. (J. Agric. Food Chem. 1966, 14,
115116). Residues in cereals by gc with a tritium ECD, see J. Burke & L. Giuffrida (J. Assoc.
Off. Anal. Chem. 1964, 47, 326342); also with microcoulometric detection and clean-up on
aluminium oxide, see D. Firestone etal. (ibid. 1963, 46, 384396) and J. F. Thompson etal.
(with ECD) (ibid. 1969, 52,12631272). See also Man. Pestic. Residue Anal., 247.
EHC 43 (1984). HSG 41 (1990). ICSC.432 (2003). IARC 20 (1979).
banned, 79/117/EEC, as amended by Regulation 850/2004.
IARC Class 2B
chlordecone 103
Oral Acute oral LD50 for albino rats 126132, rabbits 71, dogs 250 mg/kg (5% solution in
corn oil). Skin and eye Dermal LD50 for male rabbits 450 mg/kg. NOEL LD50 for long-
term feeding 14 mg/kg b.w. daily. Toxicity Class WHO (a.i.) O
ECClassification T; R24/25| R40| N; R50, R53
ECOTOXICOLOGY:
Fish Toxic to fish.
Details PM5, p. 94.
chlordimeform; chlordimeform hydrochloride

NOMENCLATURE:
Common name chlorophenamidine (JMAF); chlorodimeform (New Zealand);
chlordimeform (BSI, E-ISO, ANSI); chlordim(forme) ((m) F-ISO)
IUPACname N2-(4-chloro-o-tolyl)-N1,N1-dimethylformamidine
Chemical Abstracts name N-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide
CASRN[6164983] chlordimeform; [19750959] chlordimeform hydrochloride
ECno2282005 chlordimeform; 2432691 chlordimeform hydrochloride
DevelopmentcodesSchering 36 268; C 8514 (Ciba-Geigy)
PHYSICAL CHEMISTRY:
Composition Tech. is >96%. Mol. wt. 196.7; (hydrochloride 233.1) M.f. C10H13ClN2;
(hydrochloride C10H14Cl2N2)
Form Colourless crystals. M.p.32C; (hydrochloride 225227C (decomp.))
B.p. 163165C /14 mmHg V.p. Base: 48 mPa (20C) Kow logP = 1.8 (base), 0.201
(hydrochloride) Henry 3.78 102 Pa m3 mol1 (20C, calc.) S.g./density 1.10 (30C)
Solubility Base: In water 250 mg/l (20C). In acetone, benzene, chloroform, ethyl acetate,
hexane, methanol >200 g/l (20C). Hydrochloride: In water >500 g/l. In benzene, hexane
1, chloroform 1020, methanol >300 (all in g/l). Stability Hydrolysed first to 4-chloro-o-
tolylformamide and then to 4-chloro-o-toluidine; DT50 112 d (pH 5), 7.5 d (pH 7), 0.5 d
(pH 9, 20C) (ARS PPD).
COMMERCIALISATION:
History Acaricide reported by V. Dittrich (J. Econ. Entomol., 1966, 59, 889). Introduced by
Ciba AG (later Ciba-Geigy AG) and Schering AG. Patents GB 1039930; DE 1172081; US
3378437
APPLICATIONS:
ModeofactionSystemic acaricide and insecticide with contact, stomach, and respiratory
action. Uses Chlordimeform controls eggs and larvae of Heliothis spp. on cotton at
150225 g/ha. Also effective against the eggs and early instars of other Lepidoptera, e.g.
Chilo suppressalis, Cydia pomonella, Spodoptera littoralis, Trichoplusia ni, at 0.21.0 kg/ha,
and is effective against mites and their eggs. Phytotoxicity Injury may occur on some
104
chlordimeform; chlordimeform hydrochloride
ornamentals, tomatoes, tobacco, cucurbits, brassicas, lettuce, beans, capsicums, aubergines,

and maize. Russetting may occur with pears. Formulation types EC; SP.
PRODUCTS:
Discontinued products Fundal* (as base or hydrochloride, depending on formulation)
(Schering); Galecron* (base) (Ciba-Geigy); Spanon* (Nihon Nohyaku); Spanone*
(Schering).
ANALYSIS:
Product analysis by acid-base titration or by glc (CIPACHandbook, 1988, D, 28;
AOACMethods 18th Ed., 985.05; J. Assoc. Off. Anal. Chem., 1985, 68, 371; G.Voss et al., Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 211). Residues determined by glc of a derivative
(idem, ibid.; H. Geissbhler et al., J. Agric. Food Chem., 1971, 19, 365).
EHC 199 (1998). JMPR Evaln. I 48 (1986); JMPR Evaln. II 52 (1987). ICSC.124 (base; 1994);
ICSC.125 (hydrochloride; 1994). IARC 30 (1983).
IARC Class 3
Oral Chlordimeform: Acute oral LD50 for rats 340, rabbits 625 mg/kg. Chlordimeform
hydrochloride: Acute oral LD50 for rats 355 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits >4000 mg hydrochloride/kg. Slight skin irritant (rabbits). NOEL (2 y) for
rats 0.1 mg/kg daily, for dogs 6.25 mg/kg daily. ADI/RfD (JMPR) Temporary ADI withdrawn
[1987]; (EPA) 0.001 mg/kg b.w. [1987]. Toxicity Class WHO (a.i.) II
ECClassification R40| Xn; R21/22| N; R50, R53 (chlordimeform): R40| Xn; R22| N; R50,
R53 (chlordimeform hydrochloride) PIC Yes.
ECOTOXICOLOGY:
Fish LC50 (96 h) for trout 7.1, barbel 4.5, bluefill sunfish 1 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, undergoes N-demethylation and
hydrolysis. The principal metabolite is p-chloro-o-toluidine. Plants Metabolism in plants
is similar to that in mammals. Soil/Environment In soil, degradation is similar to
metabolism in mammals.
chloreturon
Herbicide
NOMENCLATURE:
Common name chloreturon (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(3-chloro-4-ethoxyphenyl)-1,1-dimethylurea
Chemical Abstracts name N-(3-chloro-4-ethoxyphenyl)-N,N-dimethylurea
CASRN[20782585] SmilescodeCCOc1ccc(NC(=O)N(C)C)cc1Cl
chloreturon 105

COMMERCIALISATION:
History Herbicide reported by A. Aamisepp (Proc. Swed.Weed Conf., 1977, 18, F9-F13).
Evaluated by Hoechst AG.
chlorfenac; chlorfenac-sodium
Herbicide
NOMENCLATURE:
Common name chlorfenac (BSI, E-ISO, (m) F-ISO); fenac (WSSA)
IUPACname (2,3,6-trichlorophenyl)acetic acid
Chemical Abstracts name 2,3,6-trichlorobenzeneacetic acid CASRN[85347]
chlorfenac; [2439001] chlorfenac-sodium ECno2015993
PHYSICAL CHEMISTRY: Mol. wt. 239.5; (sodium salt 261.5) M.f. C8H5Cl3O2; (sodium
salt C8H4Cl3NaO2)
Form Colourless solid. M.p.156C V.p. 1100 mPa (100C) Solubility In water 200 mg/l
(28C). Soluble in most organic solvents. Stability Photolytically decomposed by uv light.
Very stable in acidic media. Forms water-soluble salts with alkalis. pKa 3.70 (ARS PPD)
COMMERCIALISATION:
History Herbicide introduced by Amchem Products Inc. (later Rhne-Poulenc
Agrochimie) and Hooker Chemical Corp. Patents GB 860310
APPLICATIONS:
ModeofactionSystemic herbicide, absorbed primarily by roots, with translocation. Uses
Usually applied as the sodium salt, it was used to control annual grasses, broad-leaved
weeds, Elymus repens, Convolvulus arvensis and other perennial weeds in industrial
and other non-crop situations at rates up to 18 kg a.e./ha. Also used pre-em. at
2.83.4 kg a.e./ha for weed control in sugar cane. Formulation types SL .
PRODUCTS:
Discontinued products Fenac* (Amchem); Fenatrol* (sodium salt) (Amchem).
ANALYSIS:
Product analysis by glc. Residues determined by glc of suitable derivatives (G.Yip, J. Assoc.
Off. Anal. Chem., 1972, 45, 367).
for rabbits 14403160 mg/kg. NOEL In 2 y feeding trials, rats receiving 2000 mg/kg diet
showed no ill-effect. Toxicity Class WHO (a.i.) III
ECClassification Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Fish Not toxic to fish when used as recommended. Bees Not toxic to bees.
106
chlorfenac; chlorfenac-sodium
ENVIRONMENTAL FATE:
Soil/Environment Does not leach. In soil, undergoes slow microbial degradation and
persists for c.12 y.
chlorfenazole
Fungicide
NOMENCLATURE:
Common name chlorf(nazole) ((m) F-ISO); chlorfenazole (BSI, E-ISO)
IUPACname 2-(2-chlorophenyl)benzimidazole
Chemical Abstracts name 2-(2-chlorophenyl)-1H-benzimidazole
CASRN[3574967] DevelopmentcodesCUR 616
SmilescodeClc1ccccc1c2nc3ccccc3[nH]2
COMMERCIALISATION:
History Fungicide introduced by Celamerck GmbH & Co., KG (later Shell Agrar GmbH).
chlorfenethol
Acaricide
NOMENCLATURE:
Common name chlorfenethol (BSI, E-ISO, (m) E-ISO, ESA); BCPE (JMAF)
IUPACname 1,1-bis(4-chlorophenyl)ethanol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--methylbenzenemethanol
Other names DMC; DCPC CASRN[80068] ECno2012463
SmilescodeCC(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Composition May contain the 2,4- isomer. Mol. wt. 267.2 M.f. C14H12Cl2O Form
Colourless crystals. M.p.69.570C V.p. Not known exactly; said to be 4 to 8 times more
volatile than DDT. Solubility Practically insoluble in water. Readily soluble in most organic
solvents, particularly polar ones. Stability Stable to alkalis, but unstable to strong acids.
Heating leads to dehydration.
COMMERCIALISATION:
History Acaricide reported by O. Grummitt (Science, 1950, 111, 361). Introduced by
Sherwin-Williams & Co. and later by Nippon Soda Co. Ltd. Patents US 2430586.
APPLICATIONS:
ModeofactionNon-systemic acaricide with predominantly ovicidal activity, having slow
uptake and retaining effectiveness over a long period. Uses Control of spider mites (in the
chlorfenethol 107
open and under glass) in fruit, vegetables, vines, hops, cotton, and ornamental cultivation.
PRODUCTS:
Discontinued products Dimite* (Sherwin-Williams); Qikron* (Nippon Soda);
Discontinuedmixtures Milbex* (+chlorfensulphide) (Nippon Soda); Mitran*
(+chlorfenson) (Nippon Soda).
ANALYSIS:
Product analysis (1) separation from chlorfensulfide in commercial mixed formulations by
column chromatography on aluminium oxide and gravimetric determination.
(2) uv spectrophotometry in isooctane solution at 240 and 260 nm (Anal. Insectic. Acar.,
p. 432435). Residues by reaction with p-toluenesulfonic acid to give
1,1-bis(4-chlorophenyl)ethylene, and determination by gc with ECD.
Oral Acute oral LD50 for rats 9261391 mg/kg. NOEL Rats tolerated 1000 mg/kg diet fed
for 10 d (L. Peters, Proc. Soc. Exp. Biol. Med., 1947, 72, 304). Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 1.8 mg/l. Bees Not toxic to bees.
Details PM6, p. 97.
chlorfenprop; chlorfenprop-methyl
Herbicide
NOMENCLATURE:
Common name chlorfenprop (BSI, E-ISO, (m) F-ISO)
IUPACname ()-2-chloro-3-(4-chlorophenyl)propionic acid
Chemical Abstracts name ()-,4-dichlorobenzenepropanoic acid
CASRN[14437208] chlorfenprop (racemate), formerly [59604114]; [59604
103] chlorfenprop-methyl (racemate) ECno2384135 chlorfenprop-methyl
DevelopmentcodesBayer 70 533
PHYSICAL CHEMISTRY: Mol. wt. 219.1; (methyl ester 233.1) M.f. C9H8Cl2O2;
(methyl ester C10H10Cl2O2) Form Colourless liquid (ester); light brown liquid (tech. ester).
M.p.>20C (ester)
B.p. 110113C /0.1 mmHg (ester) V.p. 930 mPa (50C) (ester) S.g./density 1.30
(20C, tech. ester) Solubility In water 40 mg/l (20C, ester). Soluble in acetone, aromatic
hydrocarbons, diethyl ether and fatty oils.
COMMERCIALISATION:
History Herbicide reported by L. Eue (Z. Pflanzenkr. Pflanzenpathol. Pflanzenschutz, 1968,
Sonderheft IV, 211). Only the ()- enantiomer is herbicidal (T. Schmidt et al., Z. Naturforsch.
C. Biosci., 1976, 31C, 252). Chlorfenprop-methyl introduced by Bayer AG. Patents GB
1077194, FR 1476247.
108
chlorfenprop; chlorfenprop-methyl
APPLICATIONS:
ModeofactionContact herbicide. Uses For post-emergence control of wild oats, in
cereals (not oats), fodder crops, peas and sugar beet; applied at 4 kg/ha. Only the (-)-
enantiomer is herbicidal (T. Schmidt et al.,
Z. Naturforsch. C. Biosci., 1976, 31C, 252). Formulation types EC.
PRODUCTS:
Discontinued products Bidisin* (Bayer).
ANALYSIS:
Product analysis is by glc. Residues are also determined by glc (H. J. Jarczyk, Pflanz. Nachr.-
Bayer (Engl. Ed.) 1968, 21,360).
ECClassification Xn; R21/22| N; R50, R53 (chlorfenprop-methyl)
chlorfenson
Acaricide
NOMENCLATURE:
Common name ovatran (Argentina); ephirsulphonate* (former exception, USSR);
CPCBS (JMAF); chlorof(nizon) ((m) France); chlorfenson (BSI, E-ISO, (m) F-ISO); ovex
(ANSI, Canada)
IUPACname 4-chlorophenyl 4-chlorobenzenesulfonate
Chemical Abstracts name 4-chlorophenyl 4-chlorobenzenesulfonate Other names
chlorfenizon CASRN[80331] ECno2012704 DevelopmentcodesK 6451
(Dow) SmilescodeClc1ccc(OS(=O)(=O)c2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 303.2 M.f. C12H8Cl2O3S Form Colourless
crystalline solid, with a characteristic odour; (tech. is a colourless to tan flaky solid).
M.p.86.5C; (tech., c.80C) V.p. Negligible (25C) Solubility Practically insoluble
in water (25C). In acetone 1300, ethanol 10, xylene 780 (all in g/kg, 25C). Stability
Hydrolysed by alkali.
COMMERCIALISATION:
History Acaricide reported by E. E. Kenaga & R. W. Hummer (J. Econ. Entomol., 1949, 42,
996). Introduced by Dow Chemical Co. (later DowElanco). Patents US 2528310
APPLICATIONS:
ModeofactionA non-systemic acaricide with contact and stomach action and long
residual ovicidal activity. Uses Effective against mites of citrus and other fruit, ornamentals
and vegetable crops at 1732 g/100 l. Phytotoxicity Russetting may occur with apples and
chlorfenson 109
pears. Hops may be injured, and leaf drop may occur on roses. Formulation types WP.
PRODUCTS:
Discontinued products Ovitox* (Sipcam Phyteurop); Ovotran* (Dow); Sappiran*
(Nippon Soda); Trichlorfenson* (Bourgeois); Discontinuedmixtures Erysit Super*
(+prothoate) (Schering); Fac Super* (+prothoate) (Sopra); Mitran* (+chlorfenethol)
(Nippon Soda); Naftil* (+carbaryl) (Pepro).
ANALYSIS:
Product analysis by alkaline hydrolysis and back titration (CIPACHandbook, 1970, 1, 213; FAO
Plant Prot. Bull., 1964, 12, 17). Residues determined by glc or by colorimetry of a derivative
produced after alkaline hydrolysis (A. H. Kutschinski & E. N. Luce, Anal. Chem., 1952, 24,
1188; F. A. Gunther & L. R. Jepson, J. Econ. Entomol., 1954, 47, 1027).
JMPR Evaln. 4 (1965). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD50 for ratsc.2000 mg/kg. Skin and eye Acute percutaneous LD50 for
rats >10000 mg/kg. It may cause skin irritation. NOEL In 130 d feeding trials, no effect
was observed on rats receiving 300 mg/kg diet. ADI/RfD (JMPR) 0.01 mg/kg b.w. [1965].
Toxicity Class WHO (a.i.) III ECClassification Xn; R22| Xi; R38| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 4600, chickens 3780 mg/kg. Fish LC50 (48 h) for
carp 3.2 mg/l. Bees Not toxic to bees.
chlorfensulphide
Acaricide
NOMENCLATURE:
Common name CPAS (JMAF); chlorfensulfide ((m) F-ISO); chlorfensulphide (BSI, E-ISO)
IUPACname 4-chlorophenyl 2,4,5-trichlorobenzenediazosulfide
Chemical Abstracts name [(4-chlorophenyl)thio](2,4,5-trichlorophenyl)diazene
CASRN[2274740] SmilescodeClc1ccc(SN=Nc2cc(Cl)c(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 352.1 M.f. C12H6Cl4N2S M.p.123.5C V.p. Very
low at room temperature Solubility Practically insoluble in water. Readily soluble in
acetone, soluble in benzene. Stability Extremely stable to acids and bases.
COMMERCIALISATION:
History Introduced as a component of an acaricide by Nippon Soda Co., Ltd.
APPLICATIONS:
ModeofactionNon-systemic acaricide with contact action. Uses Control of spider
mites (in the open and under glass) in fruit, vines, hops, and ornamental cultivation.
110 chlorfensulphide
PRODUCTS:
Discontinuedmixtures Milbex* (+chlorfenethol) (Nippon Soda).
ANALYSIS:
Product: separation of the components of the commercial product by column
chromatography on aluminium oxide and determination of chlorfensulfide
spectrophotometrically at 460 nm Residues by extraction and clean-up by column
chromatography, as above, and determination by gc with ECD.
Oral Acute oral LD50 for rats 4000 mg/kg. NOEL In rats fed a diet containing 400 mg/kg
for 6 mo, no organ damage is produced and survival rate is unaffected; NOEL 800 mg/kg.
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Animals In warm-blooded animals, transformed to the 2,4,4,5-tetrachlorodiphenylsulfide,
with some further oxidation to the corresponding sulfone. Plants In plants, it is rapidly
transformed to the 2,4,4,5-tetrachlorodiphenylsulfide.
chlorflurazole
Herbicide
NOMENCLATURE:
Common name chlorflurazole (BSI, E-ISO, (m) F-ISO)
IUPACname 4,5-dichloro-2-trifluoromethylbenzimidazole
Chemical Abstracts name 4,5-dichloro-2-(trifluoromethyl)-1H-benzimidazole
CASRN[3615212] DevelopmentcodesNC 3363
SmilescodeFC(F)(F)c1nc2c(Cl)c(Cl)ccc2[nH]1
PHYSICAL CHEMISTRY: Mol. wt. 255.0 M.f. C8H3Cl2F3N2
COMMERCIALISATION:
History Herbicide evaluated by Fisons PLC (later Schering Agriculture).
chlorfluren; chlorfluren-methyl
NOMENCLATURE:
Common name chlorfluren (BSI, E-ISO); chlorflur(ne) ((m) F-ISO)
IUPACname 2-chlorofluorene-9-carboxylic acid
chlorfluren; chlorfluren-methyl 111

Chemical Abstracts name 2-chloro-9H-fluorene-9-carboxylic acid CASRN[24539

660] chlorfluren; [22909508] chlorfluren-methyl DevelopmentcodesIT-5732
(chlorfluren-methyl)
PHYSICAL CHEMISTRY: Mol. wt. 244.7; (methyl ester 258.7) M.f. C14H9ClO2; (methyl
ester C15H11ClO2)
COMMERCIALISATION:
History Plant growth regulator introduced by E. Merck (later Shell Agrar GmbH).
chlornitrofen
Herbicide
Cl
Cl O NO2
Cl
NOMENCLATURE:
Common name chlornitrofen (BSI, E-ISO); chlornitrof(ne) (F-ISO); CNP (JMAF)
IUPACname 4-nitrophenyl 2,4,6-trichlorophenyl ether
Chemical Abstracts name 1,3,5-trichloro-2-(4-nitrophenoxy)benzene
CASRN[1836777] DevelopmentcodesMO-338
Smilescode[O-][N+](=O)c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 318.5 M.f. C12H6Cl3NO3 Form Pale yellow crystals.
M.p.107C V.p. 3.2 mPa (20C) Kow logP = 5.09 S.g./density 1.623 (23C) Solubility
In water 0.25 mg/l (25C). In xylene 360 g/kg (25C). Stability Stable under neutral
conditions up to 250C.
COMMERCIALISATION:
History Herbicide introduced in Japan (1966) by Mitsui Toatsu Chemicals, Inc. (later Mitsui
Chemicals, Inc.). Patents GB 1016648; US 3316080; IT 723364 Manufacturers Mitsui
Toatsu; Sinon
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionSelective contact
herbicide. Uses Control of annual weeds in rice. Formulation types GR; EC.
PRODUCTS:
Discontinued products Mo* (Mitsui Toatsu).
ANALYSIS:
Product and residue analysis by glc with ECD (Noyaku-Seisan Gijutsu 1971, 23, 114).
Oral Acute oral LD50 for rats and mice 10000 mg/kg. Skin and eye Acute percutaneous
LD50 for rats >10000 mg/kg. Inhalation LC50 (4 h) for rats >0.52 mg/l air. NOEL (2 y) for
112 chlornitrofen
rats 0.61, mice 9.5 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Birds Acute oral LD50 for pheasants 2680 mg/kg. Fish LC50 (48 h) for carp >40, killifish
>100 mg/l. Daphnia LC50 (3 h) >40 mg/l.
chlorobenzilate
Acaricide
OH
Cl C Cl
CO2CH2CH3
NOMENCLATURE:
Common name chlorobenzilate (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPACname ethyl 4,4-dichlorobenzilate
Chemical Abstracts name ethyl 4-chloro--(4-chlorophenyl)--hydroxybenzeneacetate
CASRN[510156] ECno2081102 DevelopmentcodesG 23 992
SmilescodeCCOC(=O)C(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY: Mol. wt. 325.2 M.f. C16H14Cl2O3 Form Colourless solid.
M.p.3637.5C
B.p. 156158C /0.07 mmHg V.p. 0.12 mPa (20C) Kow logP = 4.58
Henry 3.90 103 Pa m3 mol1 (calc.) S.g./density 1.2816 (20C) Solubility In water
10 mg/l (20C). Readily soluble in most organic solvents, e.g. in acetone, dichloromethane,
methanol, toluene 1000, n-octanol 700, hexane 600 (all in g/kg, 20C). Stability Hydrolysis
DT50 7 d (pH 9), 3 d (pH 7), stable (pH 5) (all 25C) (ARS PPD).
COMMERCIALISATION:
History Acaricide reported by R. Gasser (Experientia, 1952, 8, 65). Introduced by J. R.
Geigy S.A. (later Ciba-Geigy AG). Patents BE 511234; GB 705037 Manufacturers
Makhteshim-Agan
APPLICATIONS:
ModeofactionNon-systemic acaricide with contact action and with little insecticidal
action. Uses Used for control of many species of phytophagous mites on pome fruit, citrus
fruit, vines, soya beans, cotton, tea, and vegetables at 1.01.5 kg/ha. Also used for control
of bee mites in beehives. Phytotoxicity Peaches, plums, and some varieties of apple may
be injured. Russetting is possible with pears. Formulation types EC; WP. Compatibility
Incompatible with highly alkaline materials.
PRODUCTS:
Discontinued products Acaraben* (USA) (Ciba-Geigy); Akar* (Ciba-Geigy); Folbex*
(Ciba).
chlorobenzilate 113
ANALYSIS:
Product analysis by glc with FID (E. Bartsch et al., Residue Rev., 1971, 39, 1; A. Margot &
K. Stammbach, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 65;
CIPACHandbook, 1998, H, 81; AOACMethods, 18th Ed., 971.08). Residues determined by
glc with MCD or ECD (Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1972, 6, 319;
G. Formica et al., Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1135; E. Bartsch et al.,
loc. cit.; Pestic. Anal. Manual 1979, I, 201-A, 201-G; 1979, II; R. Mestres et al., Trav. Soc. Pharm.
Montpellier, 1979, 39, 323). In drinking water by glc with ECD (AOACMethods, 18th Ed.,
990.06).
JMPR Evaln. 35 (1980). IARC 30 (1983). EU Status (1107/2009) Not approved,
IARC Class 3
for rats and rabbits >10000 mg/kg. Irritating to eyes; non-irritating to skin (rabbits).
NOEL (2 y) for rats 40 mg/kg diet (c 2.7 mg/kg daily); for dogs 500 mg/kg diet (c. 16.0
mg/kg daily). ADI/RfD (JMPR) 0.02 mg/kg b.w. [1980]; (EPA) cRfD 0.02 mg/kg b.w. [1989].
Water GV Excluded from GV derivation (U). Toxicity Class WHO (a.i.) III EPA
(formulation) III ECClassification Xn; R22| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Practically non-toxic to birds. Fish LC50 for rainbow trout 0.6, bluegill sunfish 1.8
mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, the principal metabolites identified were
p,p-dichlorobenzilic acid, p,p-dichlorobenzylhydrol, p-chlorobenzoic acid, and
p,p-dichlorobenzophenone.
1-chloro-2,4-dinitronaphthalene
Fungicide
NOMENCLATURE:
IUPACname 1-chloro-2,4-dinitronaphthalene (I)
Smilescode[O-][N+](=O)c1cc([N+](=O)[O-])c2ccccc2c1Cl
COMMERCIALISATION:
History Fungicide.
114
1-chloro-2,4-dinitronaphthalene
chloromebuform
Acaricide
NOMENCLATURE:
Common name chloromebuform (BSI, E-ISO); chlorom(buforme) ((m) F-ISO)
IUPACname N1-butyl-N2-(4-chloro-o-tolyl)-N1-methylformamidine
Chemical Abstracts name N-butyl-N-(4-chloro-2-methylphenyl)-N-
methylmethanimidamide; N-butyl-N-(4-chloro-o-tolyl)-N-methylformamidine
SmilescodeCCCCN(C)C=Nc1ccc(Cl)cc1C
COMMERCIALISATION:
History Acaricide evaluated by Ciba-Geigy AG.
PRODUCTS:
Discontinued products Ektomin* (Ciba-Geigy).
chloromethiuron
Ixodicide
Cl NHCSN(CH3)2
CH3
NOMENCLATURE:
Common name chloromethiuron (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(4-chloro-o-tolyl)-1,1-dimethyl(thiourea)
Chemical Abstracts name N-(4-chloro-2-methylphenyl)-N,N-dimethylthiourea
CASRN[28217972] DevelopmentcodesCGA 13 444; C-9140
SmilescodeCN(C)C(=S)Nc1ccc(Cl)cc1C
PHYSICAL CHEMISTRY: Mol. wt. 228.7 M.f. C10H13ClN2S Form Colourless crystals.
M.p.175C V.p. 0.0011 mPa (20C) Henry 5.03 106 Pa m3 mol1 (calc.) S.g./density
1.34 (20C) Solubility In water 50 mg/l (20C). In acetone 37, dichloromethane 40,
hexane 0.05, isopropanol 5 (all in g/kg, 20C). Stability Slowly hydrolysed, DT50 c.1 y at
5<pH<9.
COMMERCIALISATION:
History Ixodicide reported by M. von Orelli etal. (Proc.World Vet. Congr., 20th, 1975, p. 659).
Introduced by Ciba-Geigy AG. Patents BE 678543; GB 1138714
chloromethiuron 115
APPLICATIONS: Uses Controls Ixodidae including strains resistant to other ixodicides.

Used on cattle, sheep, horses and dogs in plunge dips at 1.8 g/l. Formulation types SC.
PRODUCTS:
Discontinued products Dipofene* (Ciba-Geigy).
ANALYSIS:
Product analysis by acidimetric titration. Residues determined by glc with ECD.
Oral Acute oral LD50 for rats 2500 mg tech./kg. Skin and eye Acute percutaneous LD50
for rats >2150 mg/kg. Not irritant to skin; irritant to eyes (rabbits). NOEL (90 d) for rats
10 mg/kg diet (1 mg/kg daily), for dogs 50 mg/kg diet (2 mg/kg daily). Toxicity Class WHO
(a.i.) U
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout, bluegill sunfish, carp >49 mg/l.
1-chloro-2-nitropropane
Fungicide
NOMENCLATURE:
IUPACname 1-chloro-2-nitropropane (I)
Chemical Abstracts name (I) CASRN[2425663] DevelopmentcodesFMC5916
SmilescodeCC(CCl)[N+](=O)[O-]
COMMERCIALISATION:
History Fungicide reported by Bushong (Seed Soil Treatment Newslett., 1962, 4, 39).
Introduced by FMC Corp.
APPLICATIONS:
ModeofactionFumigant soil fungicide.
PRODUCTS:
Discontinued products Lanstan* (FMC).
ICSC.423 (2001).
3-(4-chlorophenyl)-5-methylrhodanine
Fungicide, nematicide
NOMENCLATURE:
IUPACname 3-(4-chlorophenyl)-5-methylrhodanine; 3-(4-chlorophenyl)-5-methyl-2-
thioxo-1,3-thiazolidin-4-one
116
3-(4-chlorophenyl)-5-methylrhodanine
Chemical Abstracts name 3-(4-chlorophenyl)-5-methyl-2-thioxo-4-thiazolidinone

CASRN[6012926] DevelopmentcodesN 244
SmilescodeCC1SC(=S)N(C1=O)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY: Mol. wt. 257.8 M.f. C10H8ClNOS2
COMMERCIALISATION:
History Fungicide and nematicide developed by Stauffer Chemical Co.
4-chlorophenyl phenyl sulfone

Acaricide
NOMENCLATURE:
IUPACname 4-chlorophenyl phenyl sulfone
Chemical Abstracts name 1-chloro-4-(phenylsulfonyl)benzene CASRN[80002]
DevelopmentcodesR-242 SmilescodeClc1ccc(cc1)S(=O)(=O)c2ccccc2
COMMERCIALISATION:
History Acaricide introduced by Stauffer Chemical Co. (later ICI Americas).
PRODUCTS:
Discontinued products Sulphenone* (ICI).
ANALYSIS:
Residues determined by spectrometry (AOACMethods, 18th Ed., 958.08, see 11th Ed.,
29.07529.081).
chloropon
Herbicide
NOMENCLATURE:
Common name chloropon (BSI, E-ISO, (m) F-ISO)
IUPACname 2,2,3-trichloropropionic acid
Chemical Abstracts name 2,2,3-trichloropropanoic acid CASRN[3278464]
SmilescodeOC(=O)C(Cl)(Cl)CCl
COMMERCIALISATION:
History Herbicide.
chloropon 117
chloropropylate
Acaricide
IRAC12C
NOMENCLATURE:
Common name chloropropylate (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF)
IUPACname isopropyl 4,4-dichlorobenzilate
Chemical Abstracts name 1-methylethyl 4-chloro--(4-chlorophenyl)--
hydroxybenzeneacetate CASRN[5836102] DevelopmentcodesG 24 163
SmilescodeCC(C)OC(=O)C(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY: Mol. wt. 339.2 M.f. C17H16Cl2O3 Form Colourless crystals.
M.p.73C B.p. 148150C /0.5 mmHg V.p. 0.044 mPa (20C) Henry 9.95 103 Pa m3
mol1 (calc.)
S.g./density 1.35 (20C) Solubility In water 1.5 mg/l (20C). In acetone,
dichloromethane 700, hexane 50, methanol 300, n-octanol 130, toluene 500 (all in g/l, 20C).
COMMERCIALISATION:
History Acaricide reported by F. Chabousson (Phytiatr.-Phytopharm., 1956, 5, 203).
Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents BE 511234; GB 705037
APPLICATIONS:
Biochemistry Inhibitor of oxidative phosphorylation; disruptor of ATP formation.
ModeofactionNon-systemic acaricide with contact action. Uses At 3060 g/100 l on
cotton, fruit, nuts, ornamentals, sugar beet, tea and vegetables. Formulation types EC.
PRODUCTS:
Discontinued products Acaralate* (Ciba); Chlormite* (Ciba); Rospin* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with FID (E. Bartsch et al., Residue Rev., 1971, 39, 1; CIPACHandbook,
1998, H, 85; AOACMethods, 18th Ed., 971.08). Residues determined by glc with MCD.
JMPR Evaln. 19 (1972). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD50 for rats >5000 mg tech./kg. Skin and eye Not irritant to skin and
eyes of rabbits. NOEL (2 y) for rats 40 mg/kg diet, for dogs 500 mg/kg diet.
ADI/RfD (JMPR) Temporary ADI withdrawn [1972]. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Practically non-toxic to birds. Fish LC50 (96 h) for bluegill sunfish 0.66, goldfish 0.6,
rainbow trout 0.45 mg/l. Bees Slightly toxic to honeybees.
118 chloropropylate
2-chlorovinyl diethyl phosphate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname 2-chlorovinyl diethyl phosphate
Chemical Abstracts name 2-chloroethenyl diethyl phosphate CASRN[311477]
DevelopmentcodesSD 1836; OS 1836 SmilescodeCCOP(=O)(OCC)O/C=C/Cl;
without stereochemistry:CCOP(=O)(OCC)OC=CCl
PHYSICAL CHEMISTRY: Mol. wt. 214.6 M.f. C6H12ClO4P
COMMERCIALISATION:
History Insecticide developed by Shell Chemical Co.
APPLICATIONS:
chloroxuron
Herbicide
Cl O NHCON(CH3)2
HRACC2 WSSA 7; urea

NOMENCLATURE:
Common name chloroxuron (BSI, E-ISO, (m) F-ISO, ANSI, WSSA, JMAF);
chloroxifenidim* (former exception, USSR)
IUPACname 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea
Chemical Abstracts name N-[4-(4-chlorophenoxy)phenyl]-N,N-dimethylurea
CASRN[1982474] DevelopmentcodesC 1983
SmilescodeCN(C)C(=O)Nc1ccc(Oc2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 290.7 M.f. C15H15ClN2O2 Form Colourless
powder. M.p.151152C
V.p. 2.39 104 mPa (20C) Kow logP = 3.200 Henry 1.88 105 Pa m3 mol1 (calc.)
S.g./density 1.34 (20C) Solubility In water 3.7 mg/l (20C). In dichloromethane 106,
acetone 44, methanol 35, toluene 4 (all in g/kg, 20C). Soluble in DMF and chloroform;
slightly soluble in benzene and diethyl ether. Stability Decomposed by uv light. No
significant hydrolysis occurred at 30C at pH 1 or pH 13.
COMMERCIALISATION:
History Herbicide reported (Symp. New Herbic., 3rd, 1961, p. 88). Introduced by Ciba AG
(later Ciba-Geigy AG). Patents BE 593743; GB 913383
chloroxuron 119
APPLICATIONS:
site. ModeofactionSelective herbicide, absorbed principally by the roots, but also by
the leaves, with limited translocation acropetally. Uses Pre- and post-emergence control
of annual broad-leaved weeds and some grasses in peas, beans, carrots, celery, celeriac,
onions, leeks, garlic, chives, fennel, parsley, dill, tomatoes, cucurbits, soya beans, strawberries,
ornamentals, fruit trees, and conifers. Control of mosses in ornamental and sports turf, on
paths and non-crop land, and in glasshouses. Formulation types WP.
PRODUCTS:
Discontinued products Tenoran* (Ciba-Geigy).
ANALYSIS:
Product analysis by determination of the dimethylamine produced by hydrolysis, or by
tlc (CIPACHandbook, 1983, 1B, 1751; G.Voss et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 569; AOACMethods, 18th Ed., 977.06). Residues determined by hydrolysis to
4-(4-chlorophenoxy)aniline, derivatives of which are measured colorimetrically or by glc
with ECD (G.Voss et al., loc. cit.). Alternatively, glc with ECD may be used directly.
Oral Acute oral LD50 for male rats 3700, female rats 5400, mice >1000, dogs
>10000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >3000 mg/kg. Slightly
irritant to skin and eyes (rabbits). Inhalation LC50 (6 h) for rats >1.35 mg/l air.
NOEL (120 d) for rats 30 mg/kg daily; (90 d) for dogs 400 mg/kg diet (16.7 mg/kg daily).
ECOTOXICOLOGY:
Birds Slightly toxic to birds. Fish LC50 for bluegill sunfish 28, rainbow trout >100, crucian
carp >150 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, chloroxuron undergoes degradation to the monomethylated and
demethylated derivatives, followed by decarboxylation of the phenoxyphenylurea to
(4-chlorophenoxy)aniline. Soil/Environment In soil, microbial degradation leads to the
monomethylated and demethylated derivatives, and then to the (4-chlorophenoxy)aniline
derivative; DT50 10100 d. Duration of residual activity in soil isc.4 months.
120 chloroxuron
2-(4-chloro-3,5-xylyloxy)ethanol
Insecticide
NOMENCLATURE:
IUPACname 2-(4-chloro-3,5-xylyloxy)ethanol
Chemical Abstracts name 2-(4-chloro-3,5-dimethylphenoxy)ethanol
CASRN[5825796] DevelopmentcodesExperimental Chemotherapeutant 1182
SmilescodeCc1cc(OCCO)cc(C)c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 200.7 M.f. C10H13ClO2
COMMERCIALISATION:
History Insecticide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
chloroxynil
Herbicide
NOMENCLATURE:
Common name chloroxynil (BSI, E-ISO, (m) F-ISO)
IUPACname 3,5-dichloro-4-hydroxybenzonitrile (I)
SmilescodeOc1c(Cl)cc(C#N)cc1Cl
COMMERCIALISATION:
chlorphonium chloride
P[(CH2)3CH3]3 Cl
Cl CH2
Cl
NOMENCLATURE:
Common name chlorfonium chloride ((m) F-ISO); chlorphonium chloride (BSI, E-ISO)
IUPACname tributyl(2,4-dichlorobenzyl)phosphonium chloride
Chemical Abstracts name tributyl[(2,4-dichlorophenyl)methyl]phosphonium chloride
CASRN[115786] ECno2041054
Smilescode[Cl-].CCCC[P+](CCCC)(CCCC)Cc1ccc(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 397.8; 362.3 (chlorphonium ion) M.f. C19H32Cl3P;
chlorphonium ion C19H32Cl2P Form Colourless crystals. M.p.114120C V.p. 9.33
chlorphonium chloride 121

10-2 mPa (20C) Henry 3.52 10-8 Pa m3 mol1 (20C, calc.) Solubility In water 960
g/l (20C). In methanol 1030, acetone 200 (both in g/l, 20C). Insoluble in diethyl ether
and hexane. Stability Stable under normal storage conditions.
COMMERCIALISATION:
History The chloride was introduced as a plant growth regulator by the Mobil Chemical
Co. Patents US 3268323
APPLICATIONS: Uses Used to reduce internodal length in chrysanthemums,
geraniums, petunias, and other responsive ornamentals; to increase the breaking of lateral
shoots in geraniums and petunias; and to increase the number of buds and flowers in
geraniums, azaleas, and rhododendrons. It was most effective as a soil treatment for potted
ornamentals. In addition, treatment of stock plants enhances the uniformity of cuttings
taken from them. Formulation types GR; SL .
PRODUCTS:
Discontinued products Phosfleur* (Perifleur); Phosfon* (Mobil).
rabbits 750 mg/kg. Tech. product and formulations are irritating to eyes and skin.
Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassification T; R25| Xn; R21| Xi;
R36/38
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout 115 mg/l. Bees Not hazardous to bees.
ENVIRONMENTAL FATE:
Soil/Environment DT50 of chlorphonium in standard German soil 2.2 & 2.3 >28 months,
when stored under BBA conditions.
chlorphoxim
Insecticide
IRAC1B
NOMENCLATURE:
Common name chlorphoxime ((f) F-ISO); chlorphoxim (BSI, E-ISO)
IUPACname 2-(2-chlorophenyl)-2-(diethoxyphosphinothioyloxyimino)acetonitrile; O,O-
diethyl 2-chloro--cyanobenzylideneamino-oxyphosphonothioate
Chemical Abstracts name 7-(2-chlorophenyl)-4-ethoxy-3,5-dioxa-6-aza-4-phosphaoct-
6-ene-8-nitrile 4-sulfide; formerly 2-chloro--[(diethoxyphosphinothioyloxy)imino]
benzeneacetonitrile CASRN[14816207] DevelopmentcodesBAY SRA 7747;
122 chlorphoxim
Bayer 78182 SmilescodeCCOP(=S)(OCC)ON=C(C#N)c1ccccc1Cl

PHYSICAL CHEMISTRY: Mol. wt. 332.7 M.f. C12H14ClN2O3PS Form Colourless
solid. M.p.66.5C B.p. Not distillable V.p. <1 mPa (20C) Henry <1.96 101 Pa m3
mol1 (calc.) Solubility In water 1.7 mg/kg (20C). In cyclohexane, toluene 400600 g/kg
(20C).
COMMERCIALISATION:
History Insecticide reported by J. E. Hudson & W. O. Obudho (Mosq. News, 1972, 32, 37).
Introduced by Bayer AG. Patents DE 1238902
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide with contact
action, and long residual activity. Uses For control of mosquitoes and Simulium flies.
Formulation types UL; WP.
PRODUCTS:
Discontinued products Baythion C* (Bayer).
ANALYSIS:
Product analysis by hplc (CIPACHandbook, 1988, D, 42). Residues determined by glc (D. B.
Leuck & M. C. Bowman, J. Econ. Entomol., 1973, 66, 798).
PDS 32 (1978).
rats >500 mg/kg. NOEL In 90 d feeding trials, mice showed no effect at 50 mg/kg diet.
ECOTOXICOLOGY:
Birds Low toxicity to birds. Fish LC50 (96 h) for rainbow trout 0.11.0 mg/l; (48 h) for
carp 8.5 mg/l.
chlorprazophos
Insecticide
IRAC1B
NOMENCLATURE:
Common name chlorprazophos (BSI, E-ISO, (m) F-ISO)
IUPACname O-(3-chloro-7-methylpyrazolo[1,5-a]pyrimidin-2-yl) O,O-diethyl
phosphorothioate (I)
Chemical Abstracts name (I) CASRN[36145081] DevelopmentcodesHOX
2709 SmilescodeCCOP(=S)(OCC)Oc1nn2c(C)ccnc2c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 335.8 M.f. C11H15ClN3O3PS
chlorprazophos 123
COMMERCIALISATION:
History Insecticide evaluated by Bayer AG.
APPLICATIONS:
chlorprocarb
Herbicide
NOMENCLATURE:
Common name chlorprocarb (BSI, E-ISO); chlorprocarbe ((m) F-ISO)
IUPACname methyl 3-[1-(chloromethyl)propylcarbamoyloxy]carbanilate
Chemical Abstracts name 3-[(methoxycarbonyl)amino]phenyl [1-(chloromethyl)
propyl]carbamate; methyl m-hydroxycarbanilate [1-(chloromethyl)propyl]
carbamate ester CASRN[23121995] DevelopmentcodesBAS 379H (BASF)
SmilescodeCCC(CCl)NC(=O)Oc1cccc(NC(=O)OC)c1
COMMERCIALISATION:
History Herbicide introduced by BASF AG.
chlorquinox
Fungicide
NOMENCLATURE:
Common name chlorquinox (BSI, E-ISO, (m) F-ISO)
IUPACname 5,6,7,8-tetrachloroquinoxaline (I)
SmilescodeClc1c(Cl)c(Cl)c2nccnc2c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 267.9 M.f. C8H2Cl4N2
COMMERCIALISATION:
History Fungicide introduced by Fisons Ltd (later Schering Agrochemicals Ltd).
PRODUCTS:
Discontinued products Lucel* (Schering).
124 chlorquinox
chlorthiamid
Herbicide
S NH2
C
Cl Cl
HRACL WSSA 20; benzonitrile

NOMENCLATURE:
Common name DCBN (JMAF); chlorthiamid (BSI, E-ISO); chlortiamide ((f) F-ISO)
IUPACname 2,6-dichlorothiobenzamide
Chemical Abstracts name 2,6-dichlorobenzenecarbothioamide CASRN[1918134]
ECno2176377 DevelopmentcodesWL 5792 (Shell)
SmilescodeNC(=S)c1c(Cl)cccc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 206.1 M.f. C7H5Cl2NS Form Off-white solid.
M.p.151152C V.p. 0.13 mPa (20C) Kow logP = 1.77 Henry 2.82 105 Pa m3 mol1
(calc.) S.g./density 1.59 (20C) Solubility In water 950 mg/l (21C). In aromatic and
chlorinated hydrocarbons
50100 g/kg. Stability Thermally stable up to 90C. Stable in acidic solutions, but is
converted to dichlobenil in alkaline solutions.
COMMERCIALISATION:
History Herbicide reported by H. Stanford (Proc. Br.Weed Control Conf., 7th, 1964, p. 208).
Introduced by Shell Research Ltd. Discontinued by Hodogaya (2012). Patents GB 987253
Manufacturers Hodogaya
APPLICATIONS:
Biochemistry Precursor of dichlobenil. ModeofactionSystemic herbicide, absorbed
by the roots and, to some extent, by the leaves, with translocation principally acropetally.
Inhibits germination of seeds. Uses Selective control of germinating weeds in pome fruit,
currants, gooseberries, raspberries, citrus fruit, vines, olives, lavender, and ornamental plants
and shrubs. Control of bracken, grass and broad-leaved weeds in forestry; and docks in
meadows and pastures. Total weed control on non-crop land, paths, industrial areas, etc.
Formulation types GR . Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Prefix* (Shell).
ANALYSIS:
Product by potentiometric titration with silver nitrate (CIPACHandbook, 1980, 1A, 1158).
Residues by glc with ECD (K. I. Beynon et al., J. Sci. Food Agric., 1966, 17, 151155).
ICSC.852 (1996). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
chlorthiamid 125
rats >1000 mg/kg. NOEL (90 d) for rats 100 mg/kg diet. Toxicity Class WHO (a.i.) III
EPA (formulation) III ECClassification Xn; R22
ECOTOXICOLOGY:
Birds Acute oral LD50 for duck 374 mg/kg. Fish LC50 (96 h) for carp 42 mg/l. Daphnia
LC50 (48 h) 56 mg/l. Algae EC50 (48 h) 17 mg/l. Bees LD50 (oral, 48 h) 77.3 g/bee, LD50
(contact, 96 h) >100 g/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, there is rapid metabolism and 70%
elimination in the urine within 24 h. Soil/Environment In soil, chlorthiamid is
converted to dichlobenil (q.v.), which then gradually undergoes microbial degradation to
2,6-dichlorobenzamide and 2,6-dichlorobenzoic acid. Converted to dichlobenil in soil; DT50
for chlorthiamid +dichlobenilc.35 d under dry and 14 d under wet conditions. Duration
of residual activity in soil isc.57 months. The fate in crops, soils and animals has been
reviewed (K. I. Beynon & A. N. Wright, Residue Rev., 1972, 43, 23).
chlorthiophos
Insecticide
IRAC1B
NOMENCLATURE:
Common name chlorthiophos (BSI, E-ISO, (m) F-ISO, ANSI, ESA, for an isomeric reaction
mixture)
IUPACname O-2,5-dichloro-4-methylthiophenyl O,O-diethyl phosphorothioate (i, main
component); O-4,5-dichloro-2-methylthiophenyl O,O-diethyl phosphorothioate (ii, small
quantities); O-2,4-dichloro-5-methylthiophenyl O,O-diethyl phosphorothioate (iii, minor
component)
Chemical Abstracts name O-[2,5-dichloro-4-(methylthio)phenyl] O,O-diethyl
phosphorothioate (i); O-[4,5-dichloro-2-(methylthio)phenyl] O,O-diethyl phosphorothioate
(ii); O-[2,4-dichloro-5-(methylthio)phenyl] O,O-diethyl phosphorothioate (iii)
CASRN[60238564] mixed isomers; [21923239] isomer (i)
ECno2446636 for isomer (i) DevelopmentcodesS 2957 (Boehringer, Cela GmbH)
SmilescodeCCOP(=S)(OCC)Oc1cc(Cl)c(SC)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 361.2 M.f. C11H15Cl2O3PS2 Form Yellow-brown
liquid. M.p.Crystallises <25C B.p. 153158C /0.013 mmHg V.p. 0.53 mPa (25C) S.g./
density 1.345 (20C) Solubility In water c.0.3 mg/l (20C). Miscible with all common
organic solvents. Stability DT50 42 d (pH <9).
COMMERCIALISATION:
History Insecticide reported by H. Holtmann & E. Raddatz (Proc. Br. Insectic. Fungic. Conf.,
126 chlorthiophos
6th, 1971, 2, 485). Introduced by C. H. Boehringer Sohn/Cela GmbH (later Shell Agrar
GmbH). Patents DE 1298990; GB 1210826
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact and ingested
insecticide and acaricide. Uses Effective against Diptera, Hemiptera, Lepidoptera and with
some acaricidal activity. Rates 3001500 g/ha depend on pests and the crop. Formulation
types DP; EC; GR; WP.
PRODUCTS:
Discontinued products Celathion* (Shell Agrar).
ANALYSIS:
Product analysis is by bromometric titration. Residues may be determined by glc.
Oral Acute oral LD50 for male rats 10.7, female rats 7.8, mice 91.4 mg/kg.
Skin and eye Acute percutaneous LD50 for male rats 153, female rats 121, rabbits
5058 mg/kg. NOEL (2 y), based on erythrocyte cholinesterase inhibition, for rats 1.6 mg/
kg diet; (1 y) for dogs 1 mg/kg diet. Toxicity Class WHO (a.i.) Ia ECClassification T+;
R28| T; R24| N; R50, R53| concn. dep. (for isomer (i))
ECOTOXICOLOGY:
Birds LC50 (8 d) for bobwhite quail 213, mallard ducks 0.198 mg/kg diet. Fish LC50 (96 h)
for bluegill 1.3, rainbow trout 0.019 mg/l.
chlozolinate
Fungicide
Cl O
CH3
CO2CH2CH3
N
O
Cl O
FRAC2, E3; dicarboximide
NOMENCLATURE:
Common name chlozolinate (BSI, E-ISO, (m) F-ISO)
IUPACname ethyl ()-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-oxazolidine-5-carboxylate
Chemical Abstracts name ()-ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-
5-oxazolidinecarboxylate CASRN[84332865] racemate; [72391469] unstated
stereochemistry ECno2827144 DevelopmentcodesM 8164 (Agrimont)
SmilescodeCCOC(=O)C1(C)OC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
chlozolinate 127
PHYSICAL CHEMISTRY: Mol. wt. 332.1 M.f. C13H11Cl2NO5 Form Colourless, almost
odourless solid. M.p.112.6C V.p. 0.013 mPa (25C, gas saturation method) Kow logP
= 3.15 (22C) Henry 2.29 103 Pa m3 mol1 (25C, calc.) S.g./density 1.441 (20C)
Solubility In water c.2 ppm (25C). In acetone, ethyl acetate and 1,2-dichloroethane
>250, ethanol c.13, n-heptanec.2, xylenec.60 (all in g/kg, 22C). Stability Stable to
250C (under nitrogen). Stable to light. In solution, hydrolysis occurs at pH 59.
COMMERCIALISATION:
History Fungicide reported by Di Toro etal. (Atti Giornate Fitopatol., Siusi, 1980). Introduced
by Agrimont (later Isagro S.p.A.). Patents BE 874406; DE 2906574; IT 20579/78
Manufacturers Isagro
APPLICATIONS:
Biochemistry Affects mitogen-activated protein histidine kinase, in osmotic signal
transduction. ModeofactionContact fungicide with protective and curative action. Uses
Control of Botrytis spp., sclerotinia spp., and monilia spp. in ornamentals, vegetables, vines,
pome fruit, stone fruit, sunflowers and strawberries. Can be applied, at 7501000 g/ha, as a
foliar spray or as a soil drench. Formulation types SC. WP.
PRODUCTS:
Discontinued products Manderol* (Isagro); Serinal* (Isagro).
ANALYSIS:
Product and residues can be determined by glc. Details are available from Isagro.
EU Rev. Rep. 8397/VI/98 (1999). EU Status (1107/2009) Not approved, 2000/626/EC.
Oral Acute oral LD50 for rats >4500, mice >10000 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >5000 mg/kg. Non-irritating to skin and eyes (rabbits). Not
a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >10 mg/l air. NOEL (90d)
for rats 200 mg/kg diet; (1 y) for dogs 200 mg/kg diet. ADI/RfD (ECCO) 0.1 mg/kg
b.w. [1999]. Other Not mutagenic, not teratogenic. Toxicity Class WHO (a.i.) U EPA
(formulation) III ECClassification R40| N; R51, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for quail and mallard ducks >4500 mg/kg. Fish LC50 (96 h) for trout
27.5 mg/l. Daphnia LC50 (48 h) 1.18 mg/l. Algae EC50 (96 h) for Selenastrum capricornutum
30 mg/l. Bees LD50 (oral) >100 g/bee. Other beneficial Harmless to Phytoseiulus
persimilis at up to 2 recommended application rate.
ENVIRONMENTAL FATE:
Animals Chlozolinate is readily absorbed, metabolised and excreted. Metabolites
identified in urine of rats are: 3-(3,5-dichlorophenyl)-5-methyloxazolidin-2,4-dione,
N-(3,5-dichlorophenyl)-2-hydroxypropionamide, O-1-carboxyethyl-N-3,5-dichlorophenyl
carbamate, and N-(3,5-dichloro-2(or 4)-hydroxyphenyl)-2-hydroxypropionamide and its
sulfate and glucuronide conjugates. Plants In plants, chlozolinate undergoes hydrolysis and
decarboxylation processes, giving the same metabolites as those identified in animals.
128 chlozolinate
Soil/Environment In silt-loam, sandy loam and clay loam soils, hydrolysis and
decarboxylation occur; aerobic DT50 <7 h.
ciobutide
NOMENCLATURE:
Common name ciobutide (BSI, E-ISO, (m) F-ISO)
IUPACname (RS)-2-cyano-2-phenylbutyramide
Chemical Abstracts name ()--cyano--ethylbenzeneacetamide
CASRN[80544758] SmilescodeCCC(C#N)(C(=O)N)c1ccccc1
COMMERCIALISATION:
History Plant growth regulator discovered by EGYT Pharmacochemical Works.
cispermethrin
Insecticide
Cl O
CH2 O
C CH C O
Cl
CH3 CH3
An isomer pair, component of permethrin.
NOMENCLATURE:
IUPACname 3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo
propanecarboxylate; 3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethyl
cyclopropanecarboxylate
Chemical Abstracts name rel-(1R,3R)-(3-phenoxyphenyl)methyl 3-(2,2-dichloro
ethenyl)-2,2-dimethylcyclopropanecarboxylate; cis-()-(3-phenoxyphenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate CASRN[61949766],
formerly [52341330]; [54774457] (1R)-cis- resolved isomer; [54774468] (1S)-
cis- isomer DevelopmentcodesFMC 35171; NRDC 148; NRDC 167 (for the (1R)-cis-
resolved isomer)
ANALYSIS:
cispermethrin 129
CL304,415
HO2C CH2CO2H
O
Herbicide safener
NOMENCLATURE:
IUPACname 4-carboxymethylchroman-4-carboxylic acid
Chemical Abstracts name 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid
CASRN[31541578], formely [217311610] DevelopmentcodesCL304,415
SmilescodeOC(=O)CC1(CCOc2ccccc21)C(=O)O
COMMERCIALISATION:
History Herbicide safener, reported by G. E. Cary etal. (Proc. 8th IUPACInternational
Congress of Pesticide Chemistry, Washington, 1994). Developed by American Cyanamid Co.
APPLICATIONS:
Biochemistry Increases the rate of metabolism of imazethapyr in maize. Uses Safens
maize against injury by imazethapyr and other imidazolinone herbicides.
CL900167
Acaricide
F
F F
F Cl
N N
F
O O
F
F
NOMENCLATURE:
Chemical Abstracts name 4-[(4-chloro-,,-trifluoro-m-tolyl)oxy]-6-[(,,,4-
tetrafluoro-m-tolyl)oxy]-pyrimidine DevelopmentcodesCL900,167 (Shell); AC900,167
(Cyanamid)
PHYSICAL CHEMISTRY: Mol. wt. 452.7 M.f. C18H8ClF7N2O2 M.p.65C V.p.c.1
101 mPa S.g./density 1.033 (20C) Solubility In water <0.1 ppm.
130 CL900167
climbazole
Fungicide
NOMENCLATURE:
Common name climbazole (BAN)
IUPACname 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethylbutanone
Chemical Abstracts name 1-(4-chlorophenoxy)-1-(1H-imidazol-1-yl)-3,3-
dimethyl-2-butanone CASRN[38083179] DevelopmentcodesBAY MEB 6401
SmilescodeCC(C)(C)C(=O)C(Oc1ccc(Cl)cc1)n2ccnc2
PHYSICAL CHEMISTRY: Mol. wt. 292.8 M.f. C15H17ClN2O2 Form Colourless
crystalline solid. M.p.95.5C
V.p. 1.0 mPa (extrapolated to 50C) Solubility In water 5.5 mg/l (20C). In
cyclohexanone 400600, isopropanol 100200 g/kg (20C).
COMMERCIALISATION:
History Fungicide introduced by Bayer AG. Patents BE 2600800
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Uses A fungicide, effective against
Aspergillus, Candida, Paecilomyces and Penicillium spp. on various household materials, utensils
and parts of buildings.
PRODUCTS:
Discontinued products Baysan* (Bayer).
ANALYSIS:
Product analysis is by glc.
Oral Acute oral LD50 for male rats 400 mg/kg.
cliodinate
Herbicide
NOMENCLATURE:
Common name cliodinate (BSI, E-ISO, (m) F-ISO)
IUPACname 2-chloro-3,5-di-iodo-4-pyridyl acetate
Chemical Abstracts name 2-chloro-3,5-di-iodo-4-pyridinyl acetate
CASRN[69148125] DevelopmentcodesASD 2288
SmilescodeCC(=O)Oc1c(I)cnc(Cl)c1I
PHYSICAL CHEMISTRY: Mol. wt. 423.4 M.f. C7H4ClI2NO2
COMMERCIALISATION:
History Herbicide evaluated by Celamerck GmbH KG (later Shell Agrar GmbH).
cliodinate 131
cloethocarb
OCONHCH3
OCHCH2Cl
OCH3
IRAC1A
NOMENCLATURE:
Common name clo(thocarb) ((m) F-ISO); cloethocarb (BSI, E-ISO)
IUPACname 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate
Chemical Abstracts name 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate
CASRN[51487695] DevelopmentcodesBAS 263I (BASF)
SmilescodeCNC(=O)Oc1ccccc1OC(CCl)OC
PHYSICAL CHEMISTRY: Mol. wt. 259.7 M.f. C11H14ClNO4 Form Colourless crystals.
M.p.80C;
(tech.: 6975C) V.p. 0.01 mPa (20C) Henry 2.00 106 Pa m3 mol1 (calc.)
Solubility In water 1.3 g/kg (20C). In acetone, chloroform >1000, ethanol 153
(all in g/kg, 20C). Stability Non-hygroscopic. Hydrolysed by strong acids or alkalis.
COMMERCIALISATION:
History Insecticide reported by V. Harries etal. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1978, 45, 739). Introduced by BASF AG. Patents DE 2231249; GB 1426233; US 3962316
Manufacturers BASF
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide and
nematicide with contact and stomach action. Absorbed by the roots and translocated to
the foliage. Uses Control of corn rootworms on maize; colorado beetle on potatoes; and
a variety of aphids, caterpillars, scales, nematodes etc. on peanuts, potatoes, rice, sugar cane,
tobacco, sorghum, coffee, wheat, oilseed rape and alfalfa. Could be applied as a granular soil
treatment, as a seed treatment, or as bait pellets. Formulation types GR; FS; BR .
PRODUCTS:
Discontinued products Lance* (BASF).
ANALYSIS:
Product analysis by hplc. Residues determined by alkaline hydrolysis to a derivative which is
determined by hplc.
Oral Acute oral LD50 for rats 35.4, mice 70.4 mg/kg. Skin and eye Acute percutaneous
LD50 for rats 4000 mg/kg. NOEL (1 y) for dogs 0.5 mg/kg daily (capsule administration);
132 cloethocarb
for rats 25 mg/kg diet (c. 1 mg/kg daily); for mice 10 mg/kg diet (c. 1 mg/kg daily).
Toxicity Class WHO (a.i.) Ib EPA (formulation) II
ECOTOXICOLOGY:
Fish Moderately toxic to fish. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Residual activity is 37 weeks.
clofencet-potassium; clofencet
NOMENCLATURE:
Common name clofencet (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname potassium 2-(4-chlorophenyl)-3-ethyl-2,5-dihydro-5-oxopyridazine-4-
carboxylate
Chemical Abstracts name potassium 2-(4-chlorophenyl)-3-ethyl-2,5-dihydro-5-oxo-
4-pyridazinecarboxylate CASRN[82697710] clofencet-potassium; [129025543]
clofencet DevelopmentcodesMON 21233 (Monsanto); RH 754 (Rohm & Haas);
RH0754 (Rohm & Haas); FC 4001 (Zeneca); ICIS 0754 (ICI) (all clofencet-potassium);
MON 21200 (Monsanto) (clofencet)
SmilescodeCCc1c(C(=O)O)c(=O)cnn1c2ccc(Cl)cc2
PHYSICAL CHEMISTRY: Mol. wt. 316.8; 278.7 (clofencet) M.f. C13H10ClKN2O3;
clofencet C13H11ClN2O3 M.p.269C (decomp.) V.p. <1 102 mPa (25C) Kow logP =
2.2 (25C)
Henry <5.7 10-9 Pa m3 mol1 (25C, calc.) S.g./density 1.44 (20C) Solubility In
water >552; >655 (pH 5), >696 (pH 7), >658 (pH 9) (all in g/l, 23C). In methanol 16,
acetone <0.5, dichloromethane <0.4, toluene <0.4, ethyl acetate <0.5, n-hexane <0.6 (all
in g/l, 24C). Stability Stable 14 d (54C). Stable to hydrolysis in sterile aqueous pH 5, 7,
and 9 buffered solutions. Moderately persistent to aqueous photolysis; DT50 increases with
pH. pKa 2.83 (20C) (clofencet)
COMMERCIALISATION:
History Discovered by Rohm & Haas Co. (later Dow AgroSciences). Introduced by
Monsanto Co. for use in wheat in 1997.
APPLICATIONS:
ModeofactionSystemic. Inhibits pollen formation. Uses The potassium salt is a
chemical hybridising agent for wheat. Applied at 35 kg/ha. Formulation types SC.
PRODUCTS:
Discontinued products Detasselor* (potassium salt) (Monsanto); Genesis* (potassium
salt) (Monsanto).
EPA Fact Sheet, Feb. 1997. EU Status (1107/2009) Not approved, 2004/129/EC.
clofencet-potassium; clofencet 133

dermal LD50 for rats >5000 mg/kg. Eye irritant; not a skin irritant (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation EC50 for rats >3.8 mg/l. NOEL (1 y) for dogs 5.0 mg/kg
daily. ADI/RfD (EPA) cRfD 0.05 mg/kg b.w. [1997]
ECOTOXICOLOGY:
Birds Acute oral LD50 for ducks >2000, quail 1414 mg/kg. Dietary LC50 for ducks and quail
>4818 ppm. Fish LC50 for bluegill sunfish >1070, rainbow trout >990 ppb. Daphnia EC50
>1193 mg/l. Algae EbC50 (96 h) for Selenastrum capricornutum 141 mg/l; ErC50 374 mg/l.
Other aquatic spp. IC50 (14 d) for Lemna gibba (G3) >6.1 mg/l. Bees LD50 (48 h) (contact
and oral) >100 g/bee. Worms EC50 >1000 ppm.
ENVIRONMENTAL FATE:
Animals In rats, clofencet was rapidly absorbed and excreted; >78% of the administered
14
C-label was eliminated in the urine within 24 h. Clofencet was eliminated mostly
unmetabolised and mainly in the urine. At 7 days post-dosing, <1% was retained in the
tissue. Plants Clofencet is poorly metabolised in wheat, >80% of the residue in wheat
seed, andc.70% of the residue in wheat straw is unmetabolised clofencet.
Soil/Environment Metabolism of clofencet in laboratory soil studies is very slow. After
one year in loamy sand (pH 6.0, 4.5% o.m.) and silt loam (pH 7.7, 2.4% o.m.),c.70% of
the applied clofencet remains; the main route of dissipation is soil binding. Clofencet is
fairly stable to soil photolysis (7481% of parent clofencet remains after 3032 d). DT50
2028 d in aqueous solutions (pH 5, 7 and 9). In European field dissipation studies, DT50
in silty clay and silty clay loam soils (pH 6.67.8) 2566 d for three sites, although slower
degradation was seen at some sites. Batch equilibrium studies and pKa considerations
suggest that clofencet is very mobile in sand, loamy sand, and silt loam soils, but laboratory
and field studies suggest that the significant soil binding which occurs with time mitigates
the tendency towards mobility. Clofencet has the potential for runoff or soil mobility but,
in practice, because of specialised use and stewardship practices, effects of mobility and
persistence are less likely to be significant.
clofop; clofop-isobutyl
Herbicide
NOMENCLATURE:
Common name clofop (BSI, E-ISO, (m) F-ISO, WSSA)
IUPACname ()-2-[4-(4-chlorophenoxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-(4-chlorophenoxy)phenoxy]propanoic acid
CASRN[59621497] racemic clofop; [26129328] clofop (unstated stereochemistry);
[51337714] clofop-isobutyl (unstated stereochemistry) DevelopmentcodesHoe 22 870
134 clofop; clofop-isobutyl

PHYSICAL CHEMISTRY: Mol. wt. 292.7; (isobutyl ester 348.8) M.f. C15H13ClO4;
(isobutyl ester C19H21ClO4)
Form The ester is a colourless crystalline solid. M.p.3940C Solubility In water
180 mg/l (22C). Highly soluble in acetone and xylene.
COMMERCIALISATION:
History Herbicide described by F. Schwerdtle etal. (Mitt. Biol. Bundesanst. Land-Forstwirtsch.
Berlin-Dahlem, 1975, 165, 171). Clofop-isobutyl introduced by Hoechst AG.
APPLICATIONS:
ModeofactionTaken up through the leaves and roots and is selective in nearly all
cultivated dicotyledonous crops as well as in cereals. Details PM6, p. 125. Uses Clofop-
isobutyl is a post-emergence herbicide efffective against annual grasses such as Alopecurus
myosuroides, Echinochloa crus-galli, Eleusine, Panicum and Setaria spp.
Oral Acute oral LD50 for male rats 1208 mg/kg. NOEL (90 d) for dogs and male rats
32 mg/kg diet. Toxicity Class WHO (a.i.) III ECClassification Xn; R22 (clofop-isobutyl)
cloproxydim
Herbicide
NOMENCLATURE:
Common name clopropoxydim* (former WSSA); cloproxydim (BSI, ANSI, WSSA, E-ISO);
cloproxydime ((f) F-ISO)
IUPACname ()-2-[1-(3-chloroallyloxy)iminobutyl]-5-(2-ethylthiopropyl)-3-
hydroxycyclohex-2-enone
Chemical Abstracts name 2-[1-[[(3-chloro-2-propenyl)oxy]imino]butyl]-5-
[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one CASRN[95480334]
DevelopmentcodesRE-36 290
SmilescodeCCCC(=NOCC=CCl)C1=C(O)CC(CC(C)SCC)CC1=O
PHYSICAL CHEMISTRY: Mol. wt. 373.9 M.f. C18H28ClNO3S Form Liquid. V.p.
<0.013 mPa (20C)
S.g./density 1.15 (20C) Solubility Soluble in most organic solvents. Stability Unstable
in acid or alkaline solution, or on heating.
COMMERCIALISATION:
History Herbicide evaluated by Chevron Chemical Company LLC.
APPLICATIONS:
ModeofactionSelective herbicide. Uses A post-em. herbicide controlling a wide range
of annual and perennial grasses in beans, cotton, potatoes, sugar beet, and most vegetable
crops. Formulation types EC.
cloproxydim 135
PRODUCTS:
Discontinued products Selectone* (Chevron).
for rats >500 mg/kg. Other Non-mutagenic in the Ames assay.
copper bis(3-phenylsalicylate)
Fungicide
NOMENCLATURE:
IUPACname copper bis(3-phenylsalicylate)
Chemical Abstracts name bis(2-hydroxy[1,1-biphenyl]-3-carboxylato-O2,O0)copper
CASRN[5328041] Smilescode[Cu+2].Oc1c(cccc1c2ccccc2)C(=O)[O-].
Oc1c(cccc1c2ccccc2)C(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 490.0 M.f. C26H18CuO6
COMMERCIALISATION:
History Fungicide.
copper zinc chromate

Fungicide
NOMENCLATURE:
IUPACname copper zinc chromate (indefinite composition)
DevelopmentcodesCrag Fungicide 658; Experimental Fungicide 658
COMMERCIALISATION:
History Fungicide evaluated by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
coumafuryl
Rodenticide
NOMENCLATURE:
Common name coumafuryl (BSI since 1984, E-ISO, (m) F-ISO); fumarin (BSI pre-1984,
Canada); tomarin* (Turkey pre-1984)
IUPACname 3-[1-(2-furyl)-3-oxobutyl]-4-hydroxycoumarin
136 coumafuryl
Chemical Abstracts name 3-[1-(2-furanyl)-3-oxobutyl]-4-hydroxy-2H-1-

benzopyran-2-one CASRN[117522] unstated stereochemistry ECno2041955
SmilescodeCC(=O)CC(c1ccco1)c2c(O)c3ccccc3oc2=O
COMMERCIALISATION:
History Rodenticide developed by Amchem Chemical Co. (later Rhne-Poulenc
Agrochimie).
APPLICATIONS:
ModeofactionAnticoagulant rodenticide.
EHC 175 (1995). EU Status (1107/2009) Not approved, 2004/129/EC.
ECClassification T; R25, R48/25| R52, R53
coumithoate
Insecticide
IRAC1B
NOMENCLATURE:
Common name coumithoate (BSI, E-ISO, (m) F-ISO)
IUPACname O,O-diethyl O-(7,8,9,10-tetrahydro-6-oxo-6H-benzo[c]chromen-3-yl)
phosphorothioate; 3-diethoxyphosphinothioyloxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
Chemical Abstracts name O,O-diethyl O-(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]
pyran-3-yl) phosphorothioate CASRN[572485]
SmilescodeCCOP(=S)(OCC)Oc1ccc2c3CCCCc3c(=O)oc2c1
PHYSICAL CHEMISTRY: Mol. wt. 368.4 M.f. C17H21O5PS
COMMERCIALISATION:
History Insecticide introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
APPLICATIONS:
PRODUCTS:
Discontinued products Dithion* (Agrimont); Dition* (Agrimont).
ECClassification T; R25
coumithoate 137
CP 17029
Herbicide
NOMENCLATURE:
IUPACname N2,N4-bis(3-methoxypropyl)-6-methylthio-1,3,5-triazine-2,4-diamine;
2,4-bis(3-methoxypropylamino)-6-(methylthio)-1,3,5-triazine
Chemical Abstracts name N,N-bis(3-methoxypropyl)-6-(methylthio)-1,3,5-triazine-2,4-
diamine Other names MPMT CASRN[845523] DevelopmentcodesCP 17 029
SmilescodeCOCCCNc1nc(NCCCOC)nc(SC)n1
COMMERCIALISATION:
History Herbicide introduced by Monsanto Co.
PRODUCTS:
Discontinued products Lambast* (Monsanto).
credazine
Herbicide
NOMENCLATURE:
Common name credazine (JMAF)
IUPACname pyridazin-3-yl o-tolyl ether
Chemical Abstracts name 3-(2-methylphenoxy)pyridazine CASRN[14491
599] DevelopmentcodesH 722; SW-6701; SW-6721 (all Sankyo)
SmilescodeCc1ccccc1Oc2cccnn2
PHYSICAL CHEMISTRY: Mol. wt. 186.2 M.f. C11H10N2O Form Colourless needles.
M.p.78C Solubility In water 2 g/l (room temperature). Readily soluble in organic
solvents. Stability Stable to light, heat and humidity.
COMMERCIALISATION:
History Herbicide reported by T. Jojima etal. (Agric. Biol. Chem., 1968, 32, 1376; 1969, 33,
96). Introduced by Sankyo Co. Ltd. Patents JP 509596.
APPLICATIONS:
ModeofactionSelective herbicide. Uses Selective soil herbicide, used in Japan for
the control of annual grasses and some broad-leaved weeds in tomatoes, pimentoes and
strawberries, at 23 kg ha.
PRODUCTS:
Discontinued products Kusakira* (Sankyo).
ANALYSIS:
Product analysis by glc. Residues are determined by glc after separation by tlc.
Oral Acute oral LD50 for rats 3090, mice 569 mg/kg. Toxicity Class WHO (a.i.) U
138 credazine
ENVIRONMENTAL FATE:
Plants In plants, the major metabolites are (2H)-pyridazin-3-one and 3-(1--D-
glucosyloxy)pyridazine (M. Nakagawa et al., Agric. Biol. Chem., 1971, 25, 764).
Soil/Environment Moderately persistent in soil (S.Yoshimura et al., Zasso Kenkyu, 1969,
No. 7, p. 84).
crimidine
Rodenticide
NOMENCLATURE:
Common name crimidine (BSI, E-ISO, (f) F-ISO)
IUPACname 2-chloro-N,N,6-trimethylpyrimidin-4-amine
Chemical Abstracts name 2-chloro-N,N,6-trimethyl-4-pyrimidinamine
CASRN[535897] ECno2086226 SmilescodeCN(C)c1cc(C)nc(Cl)n1
PHYSICAL CHEMISTRY:
Composition Tech. containsc.20% of the non-rodenticidal 4-chloro-N,N,6-
trimethylpyrimidin-2-ylamine. Mol. wt. 171.6 M.f. C7H10ClN3 Form Tech. is a brownish
wax. M.p.87C
B.p. 140147C /4 mmHg Solubility In water 9.4 g/l (20C). In dichloromethane
6001200, isopropanol 100200 (both g/l, 20C).
COMMERCIALISATION:
History Rodenticide introduced in the early 1940s by Bayer AG. Patents US 2219858
APPLICATIONS: Formulation types AB.
PRODUCTS:
Discontinued products Castrix* (Bayer).
ANALYSIS:
Product and residue analysis is by hplc (E. Mllhoff, Pflanz.-Nachr. Bayer (Engl. Ed.), 1980, 33,
86).
Oral Acute oral LD50 for rats 1.25, rabbits 5 mg/kg. Toxicity Class WHO (a.i.) O
ECClassification T+; R28
ECOTOXICOLOGY:
Birds It is not a cumulative poison; birds are not harmed by the ingestion of a few grains
of the formulation.
crimidine 139
crotoxyphos
IRAC1B
NOMENCLATURE:
Common name crotoxyphos (BSI, E-ISO, (m) F-ISO, ESA); crotoxyfos (BAN)
IUPACname 1-phenylethyl 3-(dimethoxyphosphinoyloxy)isocrotonate; dimethyl (E)-1-
methyl-2-(1-phenylethoxycarbonyl)vinyl phosphate
Chemical Abstracts name (E)-1-phenylethyl 3-[(dimethoxyphosphinyl)oxy]-2-butenoate
CASRN[7700176] ECno2317205 DevelopmentcodesSD 4294 (Shell)
SmilescodeCOP(=O)(OC)OC(=CC(=O)OC(C)c1ccccc1)C
PHYSICAL CHEMISTRY:
Composition Tech. is 80%. Mol. wt. 314.3 M.f. C14H19O6P Form Tech. is a light straw-
coloured liquid.
B.p. 135C /0.03 mmHg (tech.) V.p. 1.9 mPa (20C) Henry 5.97 104 Pa m3 mol1
(calc.) S.g./density 1.2 (20C, tech.) Solubility In water 1 g/l (room temperature).
Soluble in acetone, ethanol, isopropanol, xylene. Stability DT50 87 h (pH 1), 35 h (pH 9)
(38C)
COMMERCIALISATION:
History Insecticide reported by C. P. Weidenback & R. L.Younger (J. Econ. Entomol., 1962,
55, 793). Introduced by the Shell Development Co. Patents US 3068268; US 3116201
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses An insecticide with a rapid action and
moderately persistent residual effect on a wide range of external insect pests of livestock
and was recommended for the control of flies, mites and ticks on cattle and pigs.
Formulation types EC. Compatibility Incompatible with most mineral carriers, except
synthetic silicas such as Colloidal Silica K320 and Hisil 233.
PRODUCTS:
Discontinued products Ciodrin* (Shell).
ANALYSIS:
Product analysis by i.r. spectroscopy or by glc. Residues determined by glc with FPD
(P. E. Porter, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 243; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 325).
Oral Acute oral LD50 for rats 52.8, mice 90 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits 384 mg/kg. NOEL In 90 d feeding trials, no effect on growth nor
histopathological change observed for male rats receiving 900 mg/kg diet, and for female
rats receiving 300 mg/kg diet. Toxicity Class WHO (a.i.) Ib ECClassification T; R24/25|
N; R50, R53| concn. dep.
140 crotoxyphos
ENVIRONMENTAL FATE:
Metabolism and breakdown in plant, animals and soil has been reviewed (K. I. Beynon et al.,
Residue Rev., 1973, 47, 55).
crufomate
Anthelmintic, insecticide
IRAC1B
NOMENCLATURE:
Common name crufomate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname 4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate
Chemical Abstracts name 2-chloro-4-(1,1-dimethylethyl)phenyl
methyl methylphosphoramidate CASRN[299865] ECno2060831
DevelopmentcodesDowco 132 SmilescodeCNP(=O)(OC)Oc1ccc(cc1Cl)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 291.7 M.f. C12H19ClNO3P Form Colourless
crystals. M.p.60C
Solubility Practically insoluble in water. Readily soluble in acetone, acetonitrile, benzene,
carbon tetrachloride; practically insoluble in light petroleum. Stability Stable at pH 7.0
but is incompatible with alkaline pesticides and is decomposed in strongly acidic media.
COMMERCIALISATION:
History Veterinary insecticide and anthelmintic reported by J. F. Landram & R. J. Shaver
(J. Parasitol., 1959, 45, 55). Introduced by Dow Chemical Co. (later DowElanco). Patents BE
579237.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide Uses
Systemic insecticide and anthelmintic used mainly for the treatment of cattle against
Warble flies, ectoparasites and helminths. Compatibility Incompatible with alkaline
pesticides.
PRODUCTS:
Discontinued products Ruelene* (DowElanco).
ANALYSIS:
Product analysis is by i.r. spectroscopy, with carbon disulfide as standard.
JMPR Evaln. 11 (1968), 19 (1972). ICSC.143 (1995).
Oral Acute oral LD50 for rats 770950, rabbits 400600 mg/kg. ADI/RfD (JMPR)
0.1 mg/kg b.w. [1968]. Toxicity Class WHO (a.i.) III ECClassification Xn; R21/22| N;
R50, R53
crufomate 141
CS 708
Insecticide
NOMENCLATURE:
IUPACname 1,1-bis(4-chlorophenyl)-2-nitrobutane (i) +1,1-bis(4-chlorophenyl)-2-
nitropropane (ii)
Chemical Abstracts name 1,1-(2-nitrobutylidene)bis[4-chlorobenzene] (i)
+1,1-(2-nitropropylidene)bis[4-chlorobenzene] (ii) CASRN[117260] (i); [117271]
(ii); [8027007] (i) +(ii), formerly [8002822] DevelopmentcodesCS 674A (i); CS
645A (ii); CS 708 (i +ii) SmilescodeCCC(C(c1ccc(Cl)cc1)c2ccc(Cl)cc2)[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 324.2 (i); 310.2 (ii) M.f. C16H15Cl2NO2 (i);
C15H13Cl2NO2 (ii)
COMMERCIALISATION:
History Insecticide introduced by Commercial Solvents Corp.
PRODUCTS:
Discontinued products Bulan* ((i)) (Commercial Solvents); Dilan* ((i) +(ii))
(Commercial Solvents); Prolan* (Commercial Solvents).
cufraneb
NOMENCLATURE:
Common name cufraneb (BSI, E-ISO); cufran(be) ((m) F-ISO)
IUPACname ethylenebis(dithiocarbamate) mixed metal complex containing not less
than 8.15% (m/m) of zinc, 8.05% (m/m) of manganese, 5.5% (m/m) of copper and 1.0%
(m/m) of iron
Chemical Abstracts name cufraneb (not defined in 9CI; see 8CI)
CASRN[11096187]
COMMERCIALISATION:
History Fungicide introduced by Universal Crop Protection Ltd.
APPLICATIONS:
Biochemistry Non-specific thiol reactant, inhibiting respiration. ModeofactionFoliar,
preventive fungicide with secondary acaricidal activity. Uses Effective against Phytophthora
infestans in potatoes and tomatoes, Nectria galligena in pome fruit, Pseudomonas mors-
prunorum in cherries, Taphrina deformans in stone fruit and Pseudopeziza ribis in bush fruit.
Also controls citrus rust mites. Formulation types WP.
PRODUCTS:
Discontinued products Cufram Z* (UCP); Discontinuedmixtures Macuprax*
(+Bordeaux mixture) (Agtrol International).
142 cufraneb
ANALYSIS:
Identified colorimetrically (CIPACHandbook, 1994, F, 320).
EHC 78 (1988); a general review of dithiocarbamates and their degradation products. EHC
200 (1998) is a general review of copper and copper compounds.
Oral Acute oral LD50 for rats 2700 mg/kg. Skin and eye Irritating to skin, eyes and
respiratory system. Toxicity Class EPA (formulation) III
ECOTOXICOLOGY:
m-cumenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPACname m-cumenyl methylcarbamate; 3-isopropylphenyl methylcarbamate
Chemical Abstracts name 3-(1-methylethyl)phenyl methylcarbamate
Other names IPMC CASRN[64006] DevelopmentcodesAC5727 (Hercules);
UC 10 854 (Union Carbide) SmilescodeCNC(=O)Oc1cccc(c1)C(C)C
COMMERCIALISATION:
History Insecticide introduced by Hercules Inc. (later Nor-Am) and Union Carbide Corp.
(later Rhne-Poulenc Agrochimie).
APPLICATIONS: Uses For use in rice.
cupric hydrazinium sulfate

Fungicide
NOMENCLATURE:
IUPACname copper(II) dihydrazinium disulfate
Chemical Abstracts name bis(hydrazine)bis(hydrogen sulfato)copper Other names
cupric hydrazinium sulfate CASRN[33271657] DevelopmentcodesMathieson 466
Smilescode[H+].[H+].N[NH2+][Cu+2][NH2+]N.[O-]S(=O)(=O)[O-].[O-]S(=O)(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 321.8 M.f. CuH10N4O8S2
COMMERCIALISATION:
History Fungicide introduced by Olin Mathieson Chemical Corp.
cupric hydrazinium sulfate 143

PRODUCTS:
Discontinued products Omazene* (Olin).
cuprobam
Fungicide
NOMENCLATURE:
Common name cuprobame ((m) France); cuprobam (BSI)
IUPACname tricopper dichloride dimethyldithiocarbamate
Chemical Abstracts name dichloro(dimethylcarbamodithioato)tricopper
CASRN[7076633]
PHYSICAL CHEMISTRY: Mol. wt. 381.7 M.f. C3H6Cl2Cu3NS2
COMMERCIALISATION:
History Fungicide.
cuprous chloride
NOMENCLATURE:
Chemical Abstracts name copper chloride CASRN[7758896]
PHYSICAL CHEMISTRY:
Form Grey tan or green powder. M.p.>430C V.p. 1.3 (546C) S.g./density 4.14
Solubility In water 0.62 g/100 g.
COMMERCIALISATION:
History First registered in USA in 1998.
APPLICATIONS: Uses Incorporated into plastic plant pots, where it inhibits root
growth when seedling roots reach the pot wall; this prevents root circling.
PRODUCTS:
Other products Migratrol (Premium).
EHC 200 (1998) is a general review of copper and copper compounds. EPA Fact Sheet, Sep.
1998.
rats 2002000 mg/kg. Eye and skin irritant. Skin sensitiser. Inhalation LC50 for rats
220 mg/l. ADI/RfD (JECFA evaluation) copper compounds 0.5 mg/kg [1982].
144 cuprous chloride

cyanatryn
Herbicide
NOMENCLATURE:
Common name cyanatryn (BSI, E-ISO); cyanatryne ((f) F-ISO)
IUPACname 2-(4-ethylamino-6-methylthio-1,3,5-triazin-2-ylamino)-2-
methylpropiononitrile
Chemical Abstracts name 2-[[4-(ethylamino)-6-(methylthio)-1,3,5-triazin-2-yl]amino]-
2-methylpropanenitrile CASRN[21689849] DevelopmentcodesWL 63 611
SmilescodeCCNc1nc(NC(C)(C)C#N)nc(SC)n1
PHYSICAL CHEMISTRY: Mol. wt. 252.3 M.f. C10H16N6S
COMMERCIALISATION:
History Herbicide reported by V.V. Dovlatyan & F.V. Avetisyan (Arm. Khim. Zh., 1972, 25,
880) and evaluated by Shell Research Ltd.
2-cyano-3-(2,4-dichlorophenyl)acrylic acid
NOMENCLATURE:
IUPACname 2-cyano-3-(2,4-dichlorophenyl)acrylic acid
Chemical Abstracts name 2-cyano-3-(2,4-dichlorophenyl)-2-propenoic acid
CASRN[6013054] DevelopmentcodesEthyl 214 SmilescodeOC(=O)/C(=C\
c1ccc(Cl)cc1Cl)/C#N;without stereochemistry:OC(=O)C(=Cc1ccc(Cl)cc1Cl)C#N
COMMERCIALISATION:
History Plant growth regulator developed by Ethyl Corp. Agrochemicals (later Nor-Am).
cyanofenphos
Insecticide
IRAC1B
NOMENCLATURE:
Common name CYP (JMAF); cyanofenphos (BSI, E-ISO); cyanophenphos (F-ISO)
IUPACname O-4-cyanophenyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-(4-cyanophenyl) O-ethyl phenylphosphonothioate
CASRN[13067931] DevelopmentcodesS-4087 (Sumitomo Chemical)
SmilescodeCCOP(=S)(Oc1ccc(C#N)cc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 303.3 M.f. C15H14NO2PS Form Tech. is a white
or slightly yellowish solid. M.p.7178C (tech.) V.p. 0.00137 mPa (20C) Solubility In
water 0.6 mg/l (30C). In methanol 89 g/kg (30C); in xylene 515 g/kg (27C).
cyanofenphos 145
COMMERCIALISATION:
History Insecticide reported by Y. Nishizawa (Bull. Agric. Chem. Soc. Japan, 1960, 24, 744).
Introduced by Sumitomo Chemical Co., Ltd. Patents JP 410930; JP 410925; GB 929738
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses An insecticide effective against penetrating
and chewing insects, cotton bollworms, gall midges, rice borers and other insects on fruits
and vegetables. Formulation types EC.
PRODUCTS:
Discontinued products Surecide* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc. Residues in milk and meat determined by glc with FPD (J. Miyamoto
et al., Nihon Noyaku Gakkaishi, 1977, 2, 1).
Oral Acute oral LD50 for rats 89 mg/kg. Skin and eye Acute percutaneous LD50 for male
rats >1000, female rats 640 mg/kg. ADI/RfD (JMPR) Temporary ADI withdrawn (1983).
Toxicity Class WHO (a.i.) II ECClassification T; R25, R39/25| Xn; R21| Xi; R36| N;
R51, R53
cyanthoate
NOMENCLATURE:
Common name cyanthoate (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname S-[N-(1-cyano-1-methylethyl)carbamoylmethyl] O,O-diethyl
phosphorothioate; N-(1-cyano-1-methylethyl)-2-(diethoxyphosphinoylthio)acetamide
Chemical Abstracts name S-[2-[(1-cyano-1-methylethyl)amino]-2-oxoethyl] O,O-diethyl
phosphorothioate CASRN[3734950] ECno2230994 DevelopmentcodesM 1568
SmilescodeCCOP(=O)(OCC)SCC(=O)NC(C)(C)C#N
COMMERCIALISATION:
History Insecticide and acaricide reported by F. Galbaiti (Proc. Br. Insectic. Fungic. Conf., 1st,
1961, 2, 507). Introduced by Montecatini S.p.A. (later Montedison S.p.A.).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact, ingested and systemic
insecticide and acaricide.
PRODUCTS:
Discontinued products Tartan* (Montedison).
146 cyanthoate
Toxicity Class WHO (a.i.) O ECClassification T+; R28| T; R24
cybutryne
Algistat
SCH3
N N
C(CH3)3
N N N
H H
NOMENCLATURE:
Common name cybutryne (BSI, E-ISO, (m) F-ISO)
IUPACname N2-tert-butyl-N4-cyclopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-cyclopropyl-N-(1,1-dimethylethyl)-
6-(methylthio)-1,3,5-triazine-2,4-diamine CASRN[28159980]
SmilescodeCC(NC1=NC(NC2CC2)=NC(SC)=N1)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 253.4 M.f. C11H19N5S
COMMERCIALISATION:
Manufacturers Zhejiang Zhongshan; Ciba
PRODUCTS:
Other products Irgarol 1510 (Ciba Specialty Chemicals).
cyclafuramid
Fungicide
NOMENCLATURE:
Common name cyclafuramid (BSI, E-ISO); cyclafuramide ((m) F-ISO)
IUPACname N-cyclohexyl-2,5-dimethyl-3-furamide
Chemical Abstracts name N-cyclohexyl-2,5-dimethyl-3-furancarboxamide
CASRN[34849428] DevelopmentcodesBAS 327F (BASF)
SmilescodeCc1cc(C(=O)NC2CCCCC2)c(C)o1
COMMERCIALISATION:
History Fungicide introduced by BASF AG.
cyclafuramid 147
cycloheximide
Fungicide, plant growth regulator
NOMENCLATURE:
Common name cycloheximide (BSI, E-ISO, (m) F-ISO)
IUPACname 3-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]
glutarimide
Chemical Abstracts name [1S-[1(S*),3,5]]-4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-
hydroxyethyl]-2,6-piperidinedione CASRN[66819]
SmilescodeCC1CC(C)C(=O)C(C1)C(O)CC2CC(=O)NC(=O)C2
PHYSICAL CHEMISTRY: Mol. wt. 281.4 M.f. C15H23NO4 Form Colourless crystals.
M.p.115.5117C Solubility In water 21 g/l (2C). Soluble in chloroform, isopropanol,
other common organic solvents; sparingly soluble in saturated hydrocarbons. Stability
Stable in neutral or acid solution, but rapidly decomposed by alkali at room temperature
to form 2,4-dimethylcyclohexanone. Specific rotation []25D 6.8 (20 g/l water)
COMMERCIALISATION:
Production Produced in culture by Streptomyces griseus and was recovered as a by-
product of streptomycin manufacture. History Antifungal antibiotic isolated by A. Whiffen
etal. (J. Bacteriol., 1946, 52, 610), agricultural uses reviewed (J. H. Ford et al., Plant Dis. Rep.,
1958, 42, 680). Introduced for crop protection by the Upjohn Co. (later Nor-Am.).
APPLICATIONS: Uses It inhibits the growth, in culture, of many plant pathogenic fungi;
it was used to control powdery mildews on ornamentals, rusts and leafspot on grasses. Its
plant growth-regulating properties were used for promoting the abscission of fruit, e.g. olives
and oranges. Formulation types WP. Compatibility Chlordane is reported to cause a
rapid loss of activity.
PRODUCTS:
Discontinued products ActiAid* (Upjohn); Actidione* (Upjohn).
ANALYSIS:
Product analysis by bioassay (G. C. Prescott et al., J. Agric. Food Chem., 1956, 4, 343; W. W.
Kilgore, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 1).
ICSC.244 (1997).
Oral Acute oral LD50 for rats 2, mice 133, guinea pigs 65, monkeys 60 mg/kg.
Toxicity Class WHO (a.i.) Ia ECClassification R68| R61| T+; R28| N; R51, R53
148 cycloheximide
cycluron
Herbicide
NOMENCLATURE:
Common name cycluron (BSI, E-ISO, (f) F-ISO, WSSA); COMU (JMAF)
IUPACname 3-cyclo-octyl-1,1-dimethylurea
Chemical Abstracts name N-cyclooctyl-N,N-dimethylurea Other names OMU
CASRN[2163691] SmilescodeCN(C)C(=O)NC1CCCCCCC1
PHYSICAL CHEMISTRY:
Composition Tech. isc.97%. Mol. wt. 198.3 M.f. C11H22N2O Form Colourless crystals.
M.p.138C;
(tech., 134138C) Solubility In water 1.1 g/l (20C). In acetone 67, benzene 55,
methanol 500 (all in g/kg, 20C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Z. Pflanzenkr. Pflanzenpathol. Pflanzenschutz,
1960, 67, 577). Introduced by BASF AG. Patents DE 1027930, DE 1062482.
APPLICATIONS: Uses A mixture of cycluron and chlorbufam was used pre-em. at 36
l Alipur/ha to control annual weeds in sugar beet and vegetables.
PRODUCTS:
Discontinuedmixtures Alipur* (+chlorbufam) (BASF).
ANALYSIS:
Product analysis is by titration. Residues may be determined by glc of the dimethylamine
produced by hydrolysis.
Oral Acute oral LD50 for rats 2600 mg/kg. Skin and eye There was no local irritation
to the backs of ears of white rabbits treated (20 h) with an aqueous solution (500 g/l).
cyometrinil
Herbicide safener
NOMENCLATURE:
Common name cyom(trinil) ((m) F-ISO); cyometrinil (BSI, WSSA, E-ISO)
IUPACname (Z)-cyanomethoxyimino(phenyl)acetonitrile
Chemical Abstracts name (Z)--[cyanomethoxyimino]benzeneacetonitrile
CASRN[78370215] (Z)- isomer; [63278331] unstated stereochemistry
DevelopmentcodesCGA 43 089 SmilescodeN#CCON=C(C#N)c1ccccc1
cyometrinil 149
PHYSICAL CHEMISTRY: Mol. wt. 185.2 M.f. C10H7N3O Form Colourless crystals.
M.p.5556C V.p. 0.0465 mPa (20C) Henry 9.07 105 Pa m3 mol1 (calc.) S.g./
density 1.260 Solubility In water
95 mg/l (20C). In benzene 550, dichloromethane 700, methanol 230, isopropanol 74 (all
in g/kg, 20C). Stability DT50 (calc.) >200 d (pH 57), 19.4 d (pH 9) (20C). Exothermic
decomposition >300C.
COMMERCIALISATION:
History Herbicide safener for 2-chloroacetanilides, introduced by Ciba-Geigy AG.
Patents BE 845827, GB 1524596.
APPLICATIONS:
Biochemistry Enhances cytochrome P450-mediated oxidative metabolism of the
herbicide (see J. Davies & J. C. Caseley, Pestic. Sci. 1999, 55(11) 10431058). Uses Increases
the tolerance of some crop plants to chloroacetanilide herbicides.
PRODUCTS:
Discontinued products Concep* (Ciba-Geigy).
ANALYSIS:
Product analysis is by glc. Residues are determined by glc using TID.
for rats >3100 mg/kg. Non-irritant to skin and eyes (rabbits). NOEL (90 d) for dogs
>100 mg/kg diet (3.1 mg/kg daily). Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds In laboratory trials it is slightly toxic to birds. Fish LC50 (96 h) for rainbow trout 5.6,
carp 11.7, bluegill 10.9 mg/l.
cypendazole
Fungicide
NOMENCLATURE:
Common name cypendazole (BSI, E-ISO, (m) F-ISO, JMAF)
IUPACname methyl 1-(5-cyanopentylcarbamoyl)benzimidazol-2-ylcarbamate
Chemical Abstracts name methyl [1-[[(5-cyanopentyl)amino]carbonyl]-1H-
benzimidazol-2-yl]carbamate CASRN[28559004] DevelopmentcodesDAM 18 654
SmilescodeCOC(=O)Nc1nc2ccccc2n1C(=O)NCCCCCC#N
COMMERCIALISATION:
History Systemic fungicide introduced by Bayer AG.
150 cypendazole
APPLICATIONS:
ModeofactionSystemic fungicide.
PRODUCTS:
Discontinued products Folicidin* (Bayer).
cyperquat; cyperquat chloride

Herbicide
NOMENCLATURE:
Common name cyperquat (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 1-methyl-4-phenylpyridinium (I)
Chemical Abstracts name (I) CASRN[48134754] cyperquat; [39794995]
cyperquat chloride DevelopmentcodesS 21 634
PHYSICAL CHEMISTRY: Mol. wt. 170.2; (cyperquat chloride 205.7) M.f. C12H12N;
(cyperquat chloride C12H12ClN)
COMMERCIALISATION:
History Cyperquat chloride introduced as a herbicide by Gulf Oil Chemicals.
cyprazine
Herbicide
NOMENCLATURE:
Common name cyprazine (BSI, E-ISO, (f) F-ISO, ANSI, WSSA)
IUPACname 6-chloro-N2-cyclopropyl-N4-isopropyl-1,3,5-triazine-2,4-diamine; 2-chloro-
4-cyclopropylamino-6-isopropylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N-cyclopropyl-N-(1-methylethyl)-1,3,5-triazine-2,4-
diamine CASRN[22936863] DevelopmentcodesS 6115
SmilescodeCC(C)Nc1nc(Cl)nc(NC2CC2)n1
COMMERCIALISATION:
History Herbicide reported by O. C. Burnside etal. (Proc. North Cent.Weed Control Conf.,
1969, p. 21). Introduced by Gulf Oil Corp.
PRODUCTS:
Discontinued products Outfox* (Gulf); Discontinuedmixtures Prefox*
(+ethiolate) (Gulf).
cyprazine 151
cyprazole
Herbicide
NOMENCLATURE:
Common name cyprazole (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]
cyclopropanecarboxamide (I)
Chemical Abstracts name (I) CASRN[42089032] DevelopmentcodesS 19 073
SmilescodeCC(C)(CCl)c1nnc(NC(=O)C2CC2)s1
PHYSICAL CHEMISTRY: Mol. wt. 259.8 M.f. C10H14ClN3OS
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Chemicals.
cyprofuram
Fungicide
NOMENCLATURE:
Common name cyprofuram (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname ()--[N-(3-chlorophenyl)cyclopropanecarboxamido]--butyrolactone
Chemical Abstracts name N-(3-chlorophenyl)-N-(tetrahydro-2-oxo-3-furanyl)
cyclopropanecarboxamide CASRN[69581335] unstated stereochemistry
ECno2740509 DevelopmentcodesSN 78 314 (Schering)
SmilescodeClc1cccc(c1)N(C2CCOC2=O)C(=O)C3CC3
PHYSICAL CHEMISTRY: Mol. wt. 279.7 M.f. C14H14ClNO3 Form Colourless
crystalline solid. M.p.9596C V.p. 0.0066 mPa (25C) Solubility In water 574 mg/l
(room temperature). In acetone, dichloromethane 500, cyclohexanone 330, ethanol 50,
n-octanol 17, xylene 60 (all in
g/kg, room temperature). Stability Stable in acid media, but hydrolysed under alkaline
conditions; DT50 37 d (pH 7), 12 h (pH 9) (25C).
COMMERCIALISATION:
History Fungicide reported by D. Baumert & H. Buschhaus (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1982, 47, 979). Introduced by Schering AG. Patents GB 1603730
APPLICATIONS:
ModeofactionSystemic fungicide. Uses Active against Oomycetes. It was
recommended against Plasmopara viticola and Phytophthora infestans but only in combination
with contact fungicides.
PRODUCTS:
Discontinued products Vinicur* (Schering).
152 cyprofuram
Oral Acute oral LD50 for rats 174, mice 296314 mg/kg. Skin and eye Acute
percutaneous LD50 for rabbits >1000 mg/kg. Toxicity Class WHO (a.i.) II
ECClassification T; R25| Xn; R21| N; R50, R53
cypromid
Herbicide
NOMENCLATURE:
Common name cypromid (BSI, E-ISO, ANSI, WSSA, JMAF); cypromide ((f) F-ISO)
IUPACname 3,4-dichlorocyclopropanecarboxanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)cyclopropanecarboxamide
CASRN[2759719] DevelopmentcodesS 6000
SmilescodeClc1ccc(NC(=O)C2CC2)cc1Cl
COMMERCIALISATION:
History Herbicide reported by T. R. Hopkins etal. (Proc. Symp. New Herbic., 2nd, Paris,
1965, p. 187). Introduced by Gulf Oil Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Clobber* (Gulf).
DAEP
Insecticide
IRAC1B
NOMENCLATURE:
Common name DAEP (JMAF)
IUPACname N-(2-dimethoxyphosphinothioylthioethyl)acetamide; S-2-acetamidoethyl
O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[2-(acetylamino)ethyl] O,O-dimethyl phosphorodithioate
CASRN[13265606] SmilescodeCOP(=S)(OC)SCCNC(=O)C
DAEP 153
COMMERCIALISATION:
History Insecticide developed by Nippon Soda Co., Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Amiphos* (Nippon Soda).
DCPM
Acaricide
NOMENCLATURE:
Common name DCPM (JMAF)
IUPACname bis(4-chlorophenoxy)methane
Chemical Abstracts name 1,1-[methylenebis(oxy)]bis[4-chlorobenzene]
Other names oxythane CASRN[555895] DevelopmentcodesK-1875
SmilescodeClc1ccc(OCOc2ccc(Cl)cc2)cc1
COMMERCIALISATION:
History Acaricide reported by L. R. Jeppson (J. Econ. Entomol., 1946, 39, 813). Introduced by
Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Neotran* (Dow).
decafentin
Fungicide
NOMENCLATURE:
Common name decafentin (BSI, E-ISO, (m) F-ISO)
IUPACname decyltriphenylphosphonium bromochlorotriphenylstannate(IV)
Chemical Abstracts name (TB-512)-decyltriphenylphosphonium
bromochlorotriphenylstannate(1-) CASRN[15652387] DevelopmentcodesA 36
SmilescodeCCCCCCCCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3.Cl[Sn-](Br)(c1ccccc1)
(c2ccccc2)c3ccccc3
PHYSICAL CHEMISTRY: Mol. wt. 868.9 M.f. C46H51BrClPSn
COMMERCIALISATION:
History Fungicide introduced by Celamerck GmbH & Co. (later Shell Agrar).
PRODUCTS:
Discontinued products Stanoram* (Shell Agrar).
154 decafentin
decarbofuran
Insecticide
NOMENCLATURE:
Common name decarbofuran (BSI, E-ISO, (m) F-ISO)
IUPACname 2,3-dihydro-2-methylbenzofuran-7-yl methylcarbamate
Chemical Abstracts name 2,3-dihydro-2-methyl-7-benzofuranyl methylcarbamate
CASRN[1563673] DevelopmentcodesBAY 62 863
SmilescodeCNC(=O)Oc1cccc2CC(C)Oc21
COMMERCIALISATION:
APPLICATIONS:
ECClassification T; R23/24/25
defenuron
Herbicide
NOMENCLATURE:
Chemical Abstracts name N-phenyl-N-methylurea CASRN[1007369]
DevelopmentcodesIPO 4328
M.p.148149.5C
V.p. 1 10-2 mPa (20C) Henry 1.18 106 Pa m3 mol1 (20C, calc.)
S.g./density 1.222 (25C) Solubility In water 1.27 g/l (20C). In ethanol 7.2 g/l, benzene
0.1 g/100 g, methylene chloride 0.331 g/100 g (all at 23C).
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Inhibits photosynthesis. ModeofactionActive by both leaf and root
uptake. Uses Control of weeds in potatoes, cereals, maize, sunflower, peas, vines, fruit and
forestry; used in combination with triazine or other herbicides. Formulation types WP.
ANALYSIS:
Product by acid hydrolysis with a mixture of sulfuric and phosphoric acids; made alkaline
and the liberated methylamine distilled off and measured by titration. Residues by
extraction with methanol, clean up by column chromatography; then acid hydrolysis,
diazotisation and coupling of the aniline with N-(1-naphthyl)ethylenediamine, followed by
determination by tlc or colorimetry.
defenuron 155
Oral Acute oral LD50 for rats 3440 mg/kg. NOEL (90 d) for rats 180 mg/kg daily.
ECOTOXICOLOGY:
Fish LC50 (120 h) for guppies 172 mg/l.
ENVIRONMENTAL FATE:
Plants Metabolism is by N-demethylation to N-phenylurea; both parent and metabolite are
conjugated as glycosides.
dehydroacetic acid
Fungicide
NOMENCLATURE:
IUPACname 2-acetyl-5-methyl-3-oxopent-4-en-5-olide (i); 3-acetyl-6-methylpyran-2,4-
dione (ii) Chemical Abstracts name 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione (i);
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (ii); 3-acetyl-2-hydroxy-6-methyl-4H-
pyran-4-one (iii) Other names DHA CASRN[520456] (i); [771039] (ii);
[16807480] (iii); [4418262] sodium salt ECno2082939; 2245801 sodium salt
SmilescodeCC(=O)C1C(=O)OC(=CC1=O)C
PHYSICAL CHEMISTRY: Mol. wt. 168.2 M.f. C8H8O4 Form Colourless powder.
M.p.109111C (subliming)
B.p. 269C V.p. 2.5 105 mPa (100C) Solubility In water 330 g/kg (25C). In
propylene glycol 480, methanol 140 (both g/kg, 25C); sparingly soluble in non-hydroxylic
organic solvents.
COMMERCIALISATION:
History Long-known as a chemical, fungicidal activity reported by P. A. Wolf (Food Technol.
(Chicago), 1950, 4, 294). Introduced by Dow Chemical Co.
APPLICATIONS: Uses Fungicide for prevention of mould growth on fresh and dried
fruit and vegetables, and for impregnation of food wrappings.
ANALYSIS:
Residue analysis is by extraction wth chloroform from acid solution, measuring the optical
density at 307 nm.
Oral Acute oral LD50 for rats 1000 mg/kg. Sodium salt: Acute oral LD50 for rats
1000 mg/kg. Toxicity Class WHO (a.i.) III ECClassification Xn; R22. (Sodium salt Xn;
R22) Details PM6, p. 152.
156 dehydroacetic acid

delachlor
Herbicide
NOMENCLATURE:
Common name delachlor (BSI, E-ISO, ANSI); d(lachlore) ((m) F-ISO)
IUPACname 2-chloro-N-(isobutoxymethyl)acet-2,6-xylidide
Chemical Abstracts name 2-chloro-N-(2,6-dimethylphenyl)-N-[(2-methylpropoxy)
methyl]acetamide CASRN[24353580] DevelopmentcodesCP 52 223
SmilescodeCC(C)COCN(C(=O)CCl)c1c(C)cccc1C
COMMERCIALISATION:
History Herbicide reported by R. F. Husted etal. (Proc. North Cent.Weed Control Conf.,
1967). Introduced by Monsanto Co.
demephion; demephion-O; demephion-S

IRAC1B
NOMENCLATURE:
Common name demephion (for a reaction product comprising demephion-O and
demephion-S) (BSI); demephion-O (i), demephion-S (ii) (for thiono and thiolo isomers,
respy.) (BSI, E-ISO, (m) F-ISO)
IUPACname (i) O,O-dimethyl O-2-methylthioethyl phosphorothioate; (ii) O,O-dimethyl
S-2-methylthioethyl phosphorothioate
Chemical Abstracts name (i) O,O-dimethyl O-[2-(methylthio)ethyl] phosphorothioate;
(ii) O,O-dimethyl S-[2-(methylthio)ethyl] phosphorothioate Other names methyl-
demeton-methyl CASRN[682804] (i); [2587908] (ii); [8065621] (i) +(ii)
ECno2116669 (i); 2199719 (ii)
PHYSICAL CHEMISTRY: Mol. wt. 216.3 M.f. C5H13O3PS2 Form Straw-coloured
liquid. B.p. 107C (decomp.)/
0.1 mmHg (i); 65C (decomp.)/0.1 mmHg (ii) S.g./density 1.198 (20C) (i); 1.218 (25C)
(ii) Solubility In water 300 mg/l (i), 3000 mg/l (ii) (both room temperature). The mixture
is miscible with most aromatic solvents, chlorobenzene and ketones; immiscible with most
aliphatic hydrocarbons.
COMMERCIALISATION:
History Systemic acaricide and insecticide reported by H. Rueppold (Wiss. Z. Martin-
Luther Univ. Halle-Wittenberg Math.-Naturwiss. Reihe, 1955, 5, 219). Introduced initially by VEB
Farbenfabrik Wolfen. Patents DE 1014017.
demephion; demephion-O; demephion-S 157

APPLICATIONS:
acaricide. Uses Effective against sucking insects, at 170510 g/ha. Compatibility Not
compatible with strongly alkaline pesticides.
PRODUCTS:
Discontinued products Atlasetox* (Atlas); Cymetox* (Cyanamid); Pyracide* (BASF);
Tinox* (E. Europe) (VEB Farbenfabrik Wolfen).
ANALYSIS:
Product analysis by separating the two isomers using column chromatography;
demephion-O is then oxidised by perchloric acid and determined as phosphate;
demephion-S is hydrolysed by alkali, the solution acidified and titrated with iodine. Residue
analysis is by isolation and oxidation to phosphate, which is measured colorimetrically by
standard procedures.
Toxicity Class WHO (a.i.) Ia ECClassification T+; R28| T; R24 (for (i) or (ii))
ENVIRONMENTAL FATE:
Plants Metabolised in plants to the sulfoxide, then slowly to the sulfone and to
phosphates.
demeton; demeton-O; demeton-S

IRAC1B
NOMENCLATURE:
Common name mercaptofos* (i) (USSR); mercaptofos teolevy* (ii) (USSR);
mercaptostiol (ii) (USSR); mercaptofostion (i) (USSR); demeton-O (i), demeton-S (ii) (for
thiono and thiolo isomers, respy.) (BSI, E-ISO, (m) F-ISO); demeton (for a reaction product
comprising demeton-O and demeton-S) (BSI, ESA)
IUPACname (i) O,O-diethyl O-2-ethylthioethyl phosphorothioate; (ii) O,O-diethyl S-2-
ethylthioethyl phosphorothioate
Chemical Abstracts name (i) O,O-diethyl O-[2-(ethylthio)ethyl] phosphorothioate; (ii)
O,O-diethyl S-[2-(ethylthio)ethyl] phosphorothioate Other names diethyl 2-ethylthioethyl
phosphorothionate (i); diethyl 2-ethylthioethyl phosphorothiolate (ii) CASRN[298
033] demeton-O; [126750] demeton-S; [8065483] demeton, formerly [8000973]
ECno2060538 demeton-O; 2048018 demeton-S
DevelopmentcodesBayer 10 756; E-1059
PHYSICAL CHEMISTRY:
Composition Reaction of 2-ethylthioethanol with O,O-diethyl phosphorochloridothioate
gives demeton asc.65:35 mixture of (i) and (ii). Mol. wt. 258.3 M.f. C8H19O3PS2
158
demeton; demeton-O; demeton-S
Form Pure demeton-O (i) and demeton-S (ii) are colourless oils. Tech. mixture is a light
yellow oil with a pronounced mercaptan-like odour. B.p. 123C /1 mmHg (demeton-O);
128C /1 mmHg (demeton-S) V.p. 38 mPa (20C, demeton-O); 35 mPa (20C,
demeton-S) Henry demeton-O; 1.64 101 Pa m3 mol1 (20C, calc.); demeton-S: 4.52
103 Pa m3 mol1 (20C, calc.) S.g./density demeton-O 1.119 (21C); demeton-S 1.132
(21C) Solubility Demeton-O (i) (room temperature): 60 mg/l water; soluble in most
organic solvents. Demeton-S (ii) (room temperature): 2 g/l water; soluble in most organic
solvents. Stability Demeton is hydrolysed by concentrated alkali, but is compatible with
most non-alkaline pesticides except water-soluble mercury compounds. The mechanism
of isomerisation of (i) to (ii) was examined by T. R. Fukuto & R. L. Metcalf (J. Am. Chem.
Soc., 1954, 76, 5103) and the self-alkylation of demeton described by D. F. Heath, (Nature
(London), 1957, 179, 377).
COMMERCIALISATION:
History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch.
Opzoekingsstn. Staat Gent, 1952, 17, 75). Introduced by Farbenfabriken Bayer AG (later Bayer
AG). Patents DE 836349; US 2571989
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic and contact insecticide
and acaricide, with some fumigant action. Demeton-S rapidly penetrates foliage. Uses
Demeton is effective against sap-feeding insects and mites. Formulation types EC.
Compatibility Demeton is compatible with most non-alkaline pesticides except water-
soluble mercury compounds.
PRODUCTS:
Discontinued products Isosystox* (demeton-S) (Bayer); Systox* (demeton) (Bayer).
ANALYSIS:
Product analysis by glc (J. G. F. Ernst, J. Chromatogr., 1977, 133, 245) or by alkaline hydrolysis
and titration of the excess of alkali (CIPACHandbook, 1970, 1, 302) or of the thiol with
iodine (ibid., 1980, 1A, 1198). Residues determined by glc (D. C. Abbott et al., Pestic. Sci.,
1970, 1, 10; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64, 733) or by oxidation to
phosphoric acid which is measured by standard colorimetric procedures (D. MacDougall,
Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 451; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 483). See also Pestic. Anal. Man., I, 302.
JMPR Evaln. 25 (1975), 27 (1976), 43 (1984). PDS 60 (1987). ICSC.861 (demeton mixed
isomers; 2002); ICSC.864 (demeton-O-methyl; 2006).
Oral Demeton: Acute oral LD50 for male rats 612, female rats 2.54.0 mg/kg. Demeton-O:
Acute oral LD50 for male rats 30 mg/kg. Demeton-S: Acute oral LD50 for rats 1.5 mg/
kg. Demeton-S sulfoxide: Acute oral LD50 for rats 2.3 mg/kg. Demeton-S sulfone: Acute
oral LD50 for rats 1.9 mg/kg. Skin and eye Acute percutaneous LD50 for male rats 14 mg
demeton/kg. NOEL (1.83 y) for rats 2 mg/kg diet (0.1 mg/kg daily) (WHO Pestic. Residue
demeton; demeton-O; demeton-S 159

Ser., 1974, 3, 217). ADI/RfD (JMPR) No ADI [1984]; (EPA) cRfD 0.00004 mg/kg b.w.
[1988] (demeton). Toxicity Class WHO (a.i.) Ia ECClassification T+; R27/28| N; R50
(demeton-O and demeton): T+; R27/28 (demeton-S)
ENVIRONMENTAL FATE:
Plants The thioether sulfur of both isomers is oxidised, metabolically, to the sulfoxide and
sulfone (R. B. March et al., J. Econ. Entomol., 1955, 48, 355).
Details PM8, Entry 03910
demeton-O-methyl
Acaricide
IRAC1B
NOMENCLATURE:
CASRN[867276] ECno2127581
PHYSICAL CHEMISTRY: Mol. wt. 230.3 M.f. C6H15O3PS2
APPLICATIONS:
PRODUCTS:
Discontinued products Knock-Out* (Crop Health).
JMPR Evaln. 27 (1976). ICSC.429 (1997).
demeton-S-methylsulphon
O
P(OCH3)2
CH3CH2SO2CH2CH2S
IRAC1B
NOMENCLATURE:
Common name demeton-S-methylsulphon (E-ISO); d(m) ((m) F-ISO); demeton-S-
methyl sulphone (BSI)
IUPACname S-2-ethylsulfonylethyl O,O-dimethyl phosphorothioate
Chemical Abstracts name S-[2-(ethylsulfonyl)ethyl] O,O-dimethyl phosphorothioate
CASRN[17040196] ECno2411095 DevelopmentcodesBayer 20 315; E 158;
M3/158 SmilescodeCCS(=O)(=O)CCSP(=O)(OC)OC
PHYSICAL CHEMISTRY: Mol. wt. 262.3 M.f. C6H15O5PS2 Form Colourless crystals.
M.p.51.6C B.p. 115C /0.0075 mmHg; 120C /0.03 mmHg V.p. 0.056 mPa (20C)
160 demeton-S-methylsulphon
Henry >7.34 10-8 Pa m3 mol1 (calc.) S.g./density 1.416 (20C)

Solubility In water >200 g/l (20C). Soluble in alcohols, ketones, and most chlorinated
hydrocarbons, e.g. dichloromethane 200 g/l. In toluene 50100 mg/l. Stability Hydrolysed
slowly in acidic media, and rapidly in alkaline media.
COMMERCIALISATION:
History Insecticide introduced by Bayer AG. Patents DE 948241
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of aphids, other sucking insects,
sawflies, and spider mites. Was normally used in combination with azinphos-methyl on fruit,
vines,ornamentals, potatoes, beet, cotton, and vegetables.
PRODUCTS:
Discontinued products Metaisosystoxsulfon* (Bayer).
ANALYSIS:
Product analysis by hydrolysis with alkali, the excess of which is determined by titration
(CIPACHandbook, 1970, 1, 312). Residues determined by glc (M. C. Bowman et al., J. Assoc.
Off. Anal. Chem., 1969, 52, 157; J. H. van der Merwe & W. B. Taylor, Pflanz.-Nachr. Bayer (Engl.
Ed.), 1971, 24, 259).
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Mtg. 65 (1992);
JMPR Evaln. I 66 (1992); JMPR Evaln. II 58 (1989) EU Status (1107/2009) Not approved,
Oral Acute oral LD50 for rats 37.5, micec.30 mg/kg. Skin and eye Acute percutaneous
LD50 for ratsc.500 mg/kg. Inhalation LC50 (4 h) for ratsc.0.2 mg/l air (aerosol).
NOEL (2 y) for rats 1 mg/kg diet. ADI/RfD (JMPR) 0.0003 mg/kg b.w. for sum of
demeton-S-methyl, demeton-S-methylsulphon and oxydemeton-methyl [1989]. Other
Acute i.p. LD50 for ratsc.20.8 mg/kg. Toxicity Class WHO (a.i.) Ib ECClassification T;
R25| Xn; R21| N; R51, R53
ECOTOXICOLOGY:
Fish LC50 for orfe 102 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, elimination is rapid, and predominantly
in the urine. Plants In plants, metabolism involves oxidation and hydrolysis, giving dimethyl
phosphate and phosphoric acid.
demeton-S-methylsulphon 161
2,4-DEP
Herbicide
NOMENCLATURE:
Common name 2,4-DEP (WSSA)
IUPACname mixture of (i) tris[2-(2,4-dichlorophenoxy)ethyl] phosphite (I) and (ii) bis[2-
(2,4-dichlorophenoxy)ethyl] phosphonate (II)
Chemical Abstracts name (I) +(II) CASRN[39420343] (i) +(ii); [94848] (i)
Developmentcodes3Y9
PHYSICAL CHEMISTRY: Mol. wt. 649.1 (i); 460.1 (ii) M.f. C24H21Cl6O6P (i);
C16H15Cl4O5P (ii)
COMMERCIALISATION:
History Herbicide introduced by Uniroyal Chemical Co., Inc.
PRODUCTS:
Discontinued products Falone* (Uniroyal).
desmetryn
Herbicide
CH3S N NHCH(CH3)2
N N
NHCH3
HRACC1 WSSA 5; 1,3,5-triazine

NOMENCLATURE:
Common name no name (Portugal); desmetryn (BSI (since 1984), E-ISO, WSSA);
desmetryne ((f) F-ISO, JMAF, BSI (before 1984))
IUPACname N2-isopropyl-N4-methyl-6-methylthio-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-methyl-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazine-
2,4-diamine CASRN[1014693] ECno2138001 DevelopmentcodesG 34 360
SmilescodeCNc1nc(NC(C)C)nc(SC)n1
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 213.3 M.f. C8H15N5S Form White powder. M.p.84
86C B.p. 339C /98.4 kPa V.p. 0.133 mPa (20C) Kow logP = 2.38 Henry 4.8 105 Pa
m3 mol1 (calc.) S.g./density 1.172 (20C) Solubility In water 580 mg/l (20C). Readily
soluble in most organic solvents, e.g. methanol 300, acetone 230, dichloromethane, toluene
200, hexane 2.6 (all in g/kg, 20C). Stability No significant hydrolysis at 70C detected at
5<pH<13. pKa 4.0, weak base
162 desmetryn
COMMERCIALISATION:
History Herbicide reported by J. G. Elliott & T. I. Cox (Proc. Br.Weed Control Conf., 6th,
1962, 2, 759). Introduced by J. R. Geigy S.A. (later Novartis Crop Protection AG).
Patents CH 337019; GB 814948 Manufacturers Novartis
APPLICATIONS:
site. ModeofactionSelective systemic herbicide, absorbed by the leaves and roots, with
translocation acropetally through the xylem, and accumulation in the apical meristems.
Uses Post-emergence control of fat-hen (Chenopodium album) and other annual
broad-leaved weeds and some grasses at 0.250.5 kg/ha in brassicas (except cauliflowers
and broccoli), herbs, onions, leeks, and conifer seedbeds. Formulation types WP.
Compatibility There may be incompatibility with some insecticides.
PRODUCTS:
Discontinued products Semeron* (Novartis).
ANALYSIS:
Product analysis by glc (CIPACHandbook, 1983, 1B, 1765). Residues determined by glc (K.
Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
LD50 for rats 2000 mg/kg. Not a skin or eye irritant (rabbits). Not a skin sensitiser when
applied epidermally; skin sensitiser when applied intradermally (guinea pigs). Inhalation
LC50 (1 h) for rats >1563 mg/m3 as WP 25. NOEL (90 d) for rats 20 mg/kg diet (1.5 mg/kg
daily); for dogs 200 mg/kg diet (6.6 mg/kg daily). ADI/RfD (BfR) 0.0014 mg/kg b.w. [1993].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification Xn; R21/22| N;
R50, R53
ECOTOXICOLOGY:
Birds LC50 (8 d) for Japanese quail >10000 mg/kg. Fish LC50 (96 h) for rainbow trout 2.2,
common carp 37 mg/l. Daphnia LC50 (48 h) 45 mg/l. Algae EC50 (72 h) for Scenedesmus
subspicatus 0.004 mg/l. Bees Not toxic to bees; LD50 (oral) >197 g/bee, (topical) >101
g/bee. Worms LC50 (14 d) for earthworms 160 mg/kg soil.
ENVIRONMENTAL FATE:
Animals Major pathways in animal metabolism are hydrolysis of the methylthio group
to form the hydroxy derivative, sulfoxidation of the methylthio group, and side-chain
dealkylation. Plants Major pathways in plant metabolism are the hydrolysis of the
methylthio group to form the hydroxy derivative, conjugation with glutathione and side-
chain dealkylation. Soil/Environment Degradation involves oxidation of the methylthio
group to sulfoxide and sulfone, hydrolysis with the introduction of a 2-hydroxy group,
dealkylation at the substituted amino groups, cleavage of the amine moiety, and ring
desmetryn 163
opening. Duration of residual activity in soil isc.3 months, DT50c.50 d. Koc 150, moderately
mobile in soil. Degradation in aquatic systems is caused by microbial processes; desmetryn
is also removed from water by adsorption to the sediment.
dialifos
O S
P(OCH2CH3)2
N S
CH
O CH2Cl
NOMENCLATURE:
Common name dialifor (ANSI, ESA, JMAF); dialifos (BSI, E-ISO); dialiphos ((m) F-ISO)
IUPACname S-2-chloro-1-phthalimidoethyl O,O-diethyl phosphorodithioate; N-[2-chloro-
1-(diethoxyphosphinothioylthio)ethyl]phthalimide
Chemical Abstracts name S-[2-chloro-1-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)
ethyl] O,O-diethyl phosphorodithioate CASRN[10311849] ECno2336893
DevelopmentcodesHercules 14503 SmilescodeCCOP(=S)(OCC)SC(CCl)N1C(=O)
c2ccccc2C1=O
PHYSICAL CHEMISTRY: Mol. wt. 393.8 M.f. C14H17ClNO4PS2 Form Colourless
crystals. M.p.6769C V.p. 133 mPa (35C) Solubility Practically insoluble in water
(<1 mg/l). In acetone 760, isophorone 400, chloroform 620, xylene 570, diethyl ether 500,
ethanol <10, hexane <10 (all in g/kg, 20C). Stability Tech. is hydrolysed in alkaline media,
DT50 2.5 h (pH 8, room temperature).
COMMERCIALISATION:
History Insecticide reported by W. R. Cothran etal. (J. Econ. Entomol., 1967, 60, 1151).
Introduced by Hercules Inc. (later Nor-Am Chemical Co.). Patents GB 1091738; US
3355353
APPLICATIONS:
acaricide with contact, stomach, and respiratory action. Uses Control of chewing and
sucking insects and spider mites on potatoes, vegetables, pome fruit, stone fruit, citrus fruit,
vines, nut trees, cotton, beet, oilseed rape, and roses. Formulation types EC.
PRODUCTS:
Discontinued products Torak* (AgrEvo, Cyanamid).
ANALYSIS:
Product by glc and uv spectrophotometry. Residues by GLC with phosphorus-specific TID
(M. A. Luke et al., J. Assoc. Off. Anal. Chem. 1981, 64, 1187).
164 dialifos

JMPR Evaln. I 45 (1985); JMPR Evaln. 27 (1976). EU Status (1107/2009) Not approved,
Oral Acute oral LD50 for male rats 4353, female rats 5, male mice 39, female mice 65,
rabbits 5871, male dogs 97 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 145
mg/kg. Mild skin and eye irritant (rabbits). NOEL In 90 d feeding trials, rats receiving 10
mg/kg diet showed inhibition of plasma and erythrocyte cholinesterases.
ADI/RfD (JMPR) ADI withdrawn (1982). Toxicity Class WHO (a.i.) II EPA (formulation) I
ECClassification T+; R28| T; R24| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 940 mg/kg. Fish LC50 (24 h) for rainbow trout
0.551.08 mg/l. Bees Low toxicity to honeybees, LD50 0.0340.038 mg/bee.
di-allate
Herbicide
NOMENCLATURE:
Common name di-allate (BSI, E-ISO); diallate ((m) F-ISO, WSSA)
IUPACname S-2,3-dichloroallyl diisopropylthiocarbamate
Chemical Abstracts name S-(2,3-dichloro-2-propenyl) bis(1-methylethyl)
carbamothioate CASRN[2303164] ECno2189611 DevelopmentcodesCP 15
336 (Monsanto) SmilescodeCC(C)N(C(C)C)C(=O)SCC(=CCl)Cl
PHYSICAL CHEMISTRY:
Composition It exists as geometric isomers which have been separated (F. H. A.
Rummens, Weed Sci., 1975, 23, 7). Mol. wt. 270.2 M.f. C10H17Cl2NOS Form Amber-
coloured liquid. M.p.2530C; <0C ((Z)- isomer); 36C ((E)- isomer) B.p. 97C /0.15
mmHg V.p. 20 mPa (25C) Kow logP = 3.29 (Agchem. Desk Ref.) Henry 3.86 101 Pa m3
mol1 (calc.) S.g./density 1.188 (25C) Solubility In water 14 mg/l (25C). Miscible with
acetone, ethanol, ethyl acetate, kerosene, isopropanol, xylene. Stability Stable to uv light;
decomposes >200C. Stable to hydrolysis.
COMMERCIALISATION:
History Herbicide reported by L. H. Hannah (Proc. North Cent.Weed Control Conf., 1959, p.
50). Introduced by Monsanto Co. Patents US 3330643; US 3330821
APPLICATIONS:
Biochemistry Inhibits lipid metabolism. ModeofactionSelective herbicide. It is
absorbed by the emerging wild oat coleoptile, toxicity being mainly at cell division. Uses A
pre- or post-planting incorporated herbicide which controls wild oats in barley, flax, forage
legumes, lentils, maize, peas, potatoes, soya beans and sugar beet. The (E)- isomer is less
effective than the (Z)- isomer in reducing height of wild oats (F. H. A. Rummens et al., Weed
di-allate 165
Sci., 1975, 23, 11). Formulation types EC; GR .

PRODUCTS:
Discontinued products Avadex* (Monsanto); Discontinuedmixtures Pyradex*
(+chloridazon) (BASF).
ANALYSIS:
Product analysis by glc. Residues determined by glc.
EHC 76 (1988); a general review of thiocarbamates. IARC 30 (1983). EU Status
(1107/2009) Not approved, Commission Regulation 2076/2002.
IARC Class 3
Oral Acute oral LD50 for rats 395, dogs 510 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits 20002500 mg/kg. Moderate irritant to skin and eyes (rabbits). NOEL
In 90 d feeding trials, rats receiving 400 mg/kg diet suffered weight loss, irritability,
hyperactivity and mild cardiac changes; but no death occurred at 1200 mg/kg diet. In beagle
dogs, adverse effects were observed at 600, but not at 125 mg/day. ADI/RfD (EPA) 0.005
mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) II ECClassification Xn; R22| R40| N; R50,
R53
ENVIRONMENTAL FATE:
Soil/Environment It competes with moisture for adsorption on soil; loss is mainly by
microbial breakdown, DT50 30 d, provided it is fully incorporated in the soil.
diamidafos
IRAC1B
NOMENCLATURE:
Common name diamidafos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname phenyl N,N-dimethylphosphorodiamidate (I)
Chemical Abstracts name (I) CASRN[1754581] DevelopmentcodesDowco
169 SmilescodeCNP(=O)(NC)Oc1ccccc1
PHYSICAL CHEMISTRY: Mol. wt. 200.2 M.f. C8H13N2O2P
COMMERCIALISATION:
History Nematicide reported by C. R.Youngson & C. A. I. Goring (Down Earth, 1963,
18(4), 3). Introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
PRODUCTS:
Discontinued products Nellite* (DowElanco).
166 diamidafos
diammonium ethylenebis(dithiocarbamate)
Fungicide
NH S
NH4 S
C CH2CH2 C
NH S NH4
S
multi-site: alkylenebis(dithiocarbamate)
NOMENCLATURE:
IUPACname diammonium ethylenebis(dithiocarbamate)
Chemical Abstracts name diammonium 1,2-ethanediylbis[carbamodithioate] Other
names amobam; amobam T (for the di-trolamine (bis-triethanolammonium) salt)
CASRN[3566107]; [33233066] di-trolamine salt
Smilescode[S-]C(=S)NCCNC(=S)[S-].[NH4+].[NH4+]
PHYSICAL CHEMISTRY: Mol. wt. 246.4 M.f. C4H14N4S4 M.p.72.572.8C
Solubility Soluble in water. Insoluble in xylene.
COMMERCIALISATION:
History Fungicide related to nabam and other dithiocarbamates. Manufactured and sold
principally in China.
APPLICATIONS:
Biochemistry Non-specific thiol reactant, inhibiting respiration. ModeofactionBroad
spectrum fungicide with protectant and curative action. Uses For control of spot disease,
anthracnose and mildew, on various crops such as rice, rubber, millet, sweet potato,
cucumber, cabbage and maize. Formulation types SL .
PRODUCTS:
Discontinued products Amobam* (Fike); Chem-O-Bam* (Tifa).
JMPR Mtg. 68 (1993); JMPR Evaln. I 69 (1993); JMPR Evaln. II 70 (1993) for metabolite
ethylenethiourea.
1,2-dibromo-3-chloropropane
Nematicide
NOMENCLATURE:
Common name DBCP (JMAF)
IUPACname 1,2-dibromo-3-chloropropane (I)
1,2-dibromo-3-chloropropane 167

DevelopmentcodesOS1897 (Shell) SmilescodeClCC(Br)CBr
PHYSICAL CHEMISTRY: Mol. wt. 236.3 M.f. C3H5Br2Cl Form Amber to dark brown
liquid, with a mildly pungent odour. B.p. 196C V.p. 1.07 105 mPa (21C)
Kow logP = 2.63 (Agchem. Desk Ref.) Henry 2.53 101 Pa m3 mol1 (calc.) S.g./density
2.08 (20C) Solubility In water 1g/kg (room temperature). Miscible with hydrocarbon
oils, acetone, iso-propanol, methanol, 1,3-dichloropropane and 1,1,2-trichlorethane.
Stability Stable in neutral and acidic media; converted to 2-bromoallyl alcohol in alkali.
COMMERCIALISATION:
History Nematicidal activity reported by C. W. McBeth & G. B. Bergeson (Plant Dis.
Rep., 1955, 39, 223). Introduced by Dow Chemical Co. (later DowElanco) and Shell
Development Co.
APPLICATIONS: Uses Soil fumigant and nematicide, effective against a wide range
of nematodes, including root-knot nematodes, at 10125 kg/ha. Phytotoxicity Many
perennial plants tolerate high concentrations, but others, including potatoes and tobacco,
require a long aeration period before planting.
PRODUCTS:
Discontinued products Fumazone* (Dow); Nemagon* (Shell).
ANALYSIS:
Residues in drinking water by glc with linearised ECD (AOACMethods, 18th Ed., 993.15).
ICSC.002 (2002). IARC 20 (1979); Suppl. 7 (1987); 71 (1999).
IARC Class 2B
Oral Acute oral LD50 for rats 170300, mice 260400 mg/kg. Water GV 0.001 mg/l (see
note on carcinogens). Other Causes sterility in humans and is mutagenic and carcinogenic
in animals. Toxicity Class WHO (a.i.) Ia ECClassification R45; R46; R60| T; R25| Xn;
R48/20/22| R52, R53
ENVIRONMENTAL FATE:
Soil/Environment Does not persist is soil to the extent that it presents an accumulation
problem.
dibutyl adipate
Insect repellent
NOMENCLATURE:
IUPACname dibutyl adipate
Chemical Abstracts name dibutyl hexanedioate CASRN[105997]
DevelopmentcodesExperimental Tick Repellent 3 SmilescodeCCCCOC(=O)
CCCCC(=O)OCCCC
168 dibutyl adipate


COMMERCIALISATION:
History Insect repellent introduced by Union Carbide Corp. (later Rhne-Poulenc
Agrochimie).
dibutyl phthalate
Insect repellent
NOMENCLATURE:
Common name dibutyl phthalate (BSI, E-ISO); phtalate de butyle (F-ISO); ()
IUPACname dibutyl phthalate
Chemical Abstracts name dibutyl 1,2-benzenedicarboxylate Other names DBP
CASRN[84742] SmilescodeCCCCOC(=O)c1ccccc1C(=O)OCCCC
COMMERCIALISATION:
History Activity as insect repellent reported by F. M. Snyder & F. A. Morton (J. Econ.
Entomol., 1947, 40, 586).
EHC 189 (1997). ICSC.036 (2002).
dibutyl succinate
Insect repellent
NOMENCLATURE:
IUPACname dibutyl succinate
Chemical Abstracts name dibutyl butanedioate CASRN[141037]
SmilescodeCCCCOC(=O)CCC(=O)OCCCC
COMMERCIALISATION:
History Insect repellent introduced by Glenn Chemical Co.
PRODUCTS:
Discontinued products Tabatrex* (Glenn); Tabutrex* (Glenn).
dibutyl succinate 169

dicamba-methyl
NOMENCLATURE:
Common name disugran (ANSI); dicamba-methyl (BSI, E-ISO, (m) F-ISO)
IUPACname methyl 3,6-dichloro-o-anisate
Chemical Abstracts name methyl 3,6-dichloro-2-methoxybenzoate CASRN[6597
780] SmilescodeCOC(=O)c1c(Cl)ccc(Cl)c1OC
COMMERCIALISATION:
History Plant growth regulator introduced by Velsicol Chemical Co. (later Sandoz AG).
PRODUCTS:
Discontinued products Racuza* (Sandoz).
dicapthon
Insecticide
IRAC1B
NOMENCLATURE:
Common name dicapthon (ESA, ex-ANSI)
CASRN[2463845] DevelopmentcodesAC4124 SmilescodeCOP(=S)(OC)
Oc1ccc(cc1Cl)[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 297.7 M.f. C8H9ClNO5PS
COMMERCIALISATION:
History Insecticide reported by T. B. Davich & J. W. Apple (J. Econ. Entomol., 1951, 44, 528)
and by J. C. Gaines (ibid., p. 750). Introduced by American Cyanamid Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Dicapton* (Cyanamid).
170 dicapthon
dichlone
Algicide, fungicide
O
Cl
Cl
O
NOMENCLATURE:
Common name dichlone (BSI, E-ISO, (m) F-ISO, JMAF)
IUPACname 2,3-dichloro-1,4-naphthoquinone
Chemical Abstracts name 2,3-dichloro-1,4-naphthalenedione CASRN[117
806] ECno2042105 DevelopmentcodesUSR 604 (to Uniroyal)
SmilescodeClC1=C(Cl)C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
Composition Tech. isc.95%. Mol. wt. 227.0 M.f. C10H4Cl2O2 Form Yellow crystals.
M.p.193C (subliming >32C); tech., 188C B.p. 275C /2 mmHg V.p. 0.01 mPa (ARS
PPD) Kow logP = 5.62 (Agchem. Desk Ref.) Solubility In water 0.1 mg/l (25C). In xylene
and 1,2-dichlorobenzene,c.4%. Moderately soluble in acetone, diethyl ether, benzene,
ethyl acetate, acetic acid, DMF, and dioxane. Sparingly soluble in alcohols. Stability In the
dry state, stable to light and heat. In solution, slowly decomposed by light. Stable in acidic
media, but hydrolysed by alkalis.
COMMERCIALISATION:
History Fungicidal properties of this established chemical reported by W. P. ter Horst &
E. L. Felix (Ind. Eng. Chem., 1943, 35, 1255). Introduced by Uniroyal Chemical Co., Inc. and
by FMC Corp. Patents US 2302384; US 2349772 (to Uniroyal) Manufacturers Zhejiang
Heyi
APPLICATIONS:
ModeofactionFoliar fungicide with protective action. Uses Fungicidal control in fruit,
vegetables, ornamentals, and field crops. Particular uses included control of blossom blights,
scab on apples and pears, and brown rot of stone fruit. Also used to control blue-green
Algae in ponds, lakes, and swimming pools. Formulation types WP. Compatibility
Incompatible with petroleum oils, dinitro compounds, organomercury compounds, calcium
arsenate, lime sulfur, Bordeaux mixture, nicotine, and emulsifiable concentrate formulations.
PRODUCTS:
Discontinued products Kolo* (FMC); Phygon* (Uniroyal).
ANALYSIS:
Product analysis by colorimetry after alkaline hydrolysis to the sodium salt of 2-chloro-
3-hydroxy-1,4-naphthoquinone (D. K. Gullstrom & H. P. Burchfield, Anal. Chem., 1948, 20,
1174; J. R. Lane, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 141). Residues
dichlone 171
determined by glc (Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 584) or by colorimetry
(AOACMethods, 18th Ed., 965.36).
rabbits 5000 mg/kg. Irritating to skin under warm conditions. NOEL In 2 y feeding trials,
rats receiving 1500 mg/kg diet showed no ill-effects. ADI/RfD (EPA) 0.08 mg/kg b.w.
[1989]. Toxicity Class WHO (a.i.) III ECClassification Xn; R22| Xi; R36/38| N; R50,
R53
ECOTOXICOLOGY:
Fish LC50 (48 h) for brown trout 0.31 mg/l. Daphnia LC50 0.014 mg/l. Bees Not toxic to
bees.
ENVIRONMENTAL FATE:
Plants In plant cells, both chlorine atoms are replaced by sulfhydryl groups to give a
substituted dimercapto compound.
dichloralurea
Herbicide
NOMENCLATURE:
Common name DCU (WSSA); dichloralurea (BSI, E-ISO); dichloralur(e) (F-ISO); are
accepted in lieu of a common name
IUPACname 1,3-bis(2,2,2-trichloro-1-hydroxyethyl)urea
Chemical Abstracts name N,N-bis(2,2,2-trichloro-1-hydroxyethyl)urea
CASRN[116529] DevelopmentcodesCrag Herbicide 2
SmilescodeOC(NC(=O)NC(O)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
COMMERCIALISATION:
History Herbicide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Crag Herbicide 2* (Union Carbide).
dichlorflurenol; dichlorflurenol-methyl
NOMENCLATURE:
Common name dichlorflurenol (BSI from 1990, E-ISO); dichloroflur(nol) ((m) F-ISO);
dichlorflurecol* (BSI until 1990, Canada)
172
dichlorflurenol; dichlorflurenol-methyl
IUPACname 2,7-dichloro-9-hydroxyfluorene-9-carboxylic acid

Chemical Abstracts name 2,7-dichloro-9-hydroxy-9H-fluorene-9-carboxylic acid
CASRN[21634968] dichlorflurenol-methyl DevelopmentcodesIT-5733
PHYSICAL CHEMISTRY:
Composition Dichlorflurenol-methyl is present as a minor component of tech.
chlorflurenol-methyl (q.v.). Mol. wt. 295.1; (methyl ester 309.2) M.f. C14H8Cl2O3; (methyl
ester C15H10Cl2O3)
COMMERCIALISATION:
History Dichlorflurenol-methyl introduced as a plant growth regulator by E. Merck (later
Shell Agrar GmbH).
dichlormate
Herbicide
NOMENCLATURE:
Common name dichlormate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 3,4-dichlorobenzyl methylcarbamate
Chemical Abstracts name (3,4-dichlorophenyl)methyl methylcarbamate
CASRN[1966581] dichlormate; [62046371] tech. grade containing 2,3-dichloro-
analogue DevelopmentcodesUC 22 463A (pure dichlormate); UC 22 463 (TC grade)
SmilescodeCNC(=O)OCc1ccc(Cl)c(Cl)c1
COMMERCIALISATION:
History Herbicide reported by R. A. Herrett & R.V. Berthold (Science, 1965, 149, 191).
Introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Rowmate* (Union Carbide).
1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate
Fungicide
NOMENCLATURE:
IUPACname 1,3-dichloro-1,1,3,3-tetrafluoropropane-2,2-diol (i); 1,3-dichloro-1,1,3,3,-
tetrafluoroacetone hydrate (ii)
Chemical Abstracts name 1,3-dichloro-1,1,3,3-tetrafluoro-2,2-propanediol (i);
1,3-dichloro-1,1,3,3-tetrafluoro-2-propanone hydrate (ii) CASRN[993588] (i);
[127219] (ii) DevelopmentcodesGC 9832
1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate 173

PHYSICAL CHEMISTRY: Mol. wt. 216.9 M.f. C3H2Cl2F4O2

COMMERCIALISATION:
History Fungicide reported by D. W. George (Plant Dis. Rep., 1964, 48, 162). Introduced by
Allied Chemical Corp.
1,1-dichloro-1-nitroethane
Insecticide
NOMENCLATURE:
IUPACname 1,1-dichloro-1-nitroethane (I)
SmilescodeCC(Cl)(Cl)[N+](=O)[O-]
COMMERCIALISATION:
History Insecticidal activity reported by W. C. OKane & H. W. Smith (J. Econ. Entomol.,
1941, 34, 438). Introduced by Commercial Solvents Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Ethide* (Commercial Solvents).
Oral Acute oral LD50 for rats 410 mg/kg (Shibuya). ECClassification T; R23/24/25
1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
Insecticide
NOMENCLATURE:
IUPACname 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
Chemical Abstracts name 1,1-(2,2-dichloroethylidene)bis[4-ethylbenzene]
Other names ethylan CASRN[72560] DevelopmentcodesQ-137 (Rohm &
Haas); Bayer 63138 SmilescodeCCc1ccc(cc1)C(C(Cl)Cl)c2ccc(CC)cc2
PHYSICAL CHEMISTRY: Mol. wt. 307.3 M.f. C18H20Cl2 Form Crystalline solid; (tech.
is a wax). M.p.6061C; (tech., 40C) Solubility Practically insoluble in water. Soluble
in most aromatic solvents and in dichloromethane.
COMMERCIALISATION:
History Insecticide introduced by Rohm & Haas Co. Patents US 2464000, US 2881111,
US 2883428.
174
1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
APPLICATIONS:
ModeofactionNon-systemic insecticide with useful specificity. Uses For control of pear
psylla, and use against leafhoppers and various larvae on vegetable crops, at 116 kg/ha.
Also used domestically for the control of clothes moth and carpet beetles.
PRODUCTS:
Discontinued products Perthane* (Rohm & Haas).
ANALYSIS:
Residues determined by glc, tlc or paper chromatography (AOACMethods 18th Ed., 970.52)
or by glc with ECD of a dehydrochlorinated derivative (ibid., 973.39). See also Pestic. Anal.
Man., I, 303, 304.
ENVIRONMENTAL FATE:
Soil/Environment Moderately persistent in soil.
O-2,5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O-2,5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate
Chemical Abstracts name O-(2,5-dichloro-4-iodophenyl) O-ethyl
ethylphosphonothioate CASRN[25177279] DevelopmentcodesC 18 244
SmilescodeCCOP(=S)(CC)Oc1cc(Cl)c(I)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 425.1 M.f. C10H12Cl2IO2PS
COMMERCIALISATION:
History Insecticide introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
2,4-dichlorophenyl benzenesulfonate
Acaricide
NOMENCLATURE:
IUPACname 2,4-dichlorophenyl benzenesulfonate (I)
Chemical Abstracts name (I) Other names DCPBS CASRN[97165]
DevelopmentcodesEM-923; GC-923 SmilescodeClc1ccc(OS(=O)(=O)c2ccccc2)
c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 303.2 M.f. C12H8Cl2O3S
2,4-dichlorophenyl benzenesulfonate 175

COMMERCIALISATION:
History Acaricide introduced by Allied Chemical Corp., Agrochemical Division (later
Hopkins Agricultural Chemical Co.).
PRODUCTS:
Discontinued products Genite* (Allied); Genitol* (Allied).
(RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)succinimide
Fungicide
NOMENCLATURE:
IUPACname (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)succinimide
Chemical Abstracts name ()-1-(3,5-dichlorophenyl)-3-(methoxymethyl)-2,5-
pyrrolidinedione Other names metomeclan* (unadopted proposed common name)
CASRN[81949884] DevelopmentcodesCo 6054
SmilescodeCOCC1CC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
COMMERCIALISATION:
History Fungicide evaluated by Wacker-Chemie GmbH.
PRODUCTS:
Discontinued products Drawifol* (Wacker).
N-3,5-dichlorophenylsuccinimide
Fungicide
NOMENCLATURE:
IUPACname N-3,5-dichlorophenylsuccinimide
Chemical Abstracts name 1-(3,5-dichlorophenyl)-2,5-pyrrolidinedione
CASRN[24096535] DevelopmentcodesS-47127
SmilescodeClc1cc(Cl)cc(c1)N2C(=O)CCC2=O
COMMERCIALISATION:
History Fungicide introduced by Sumitomo Chemical Co., Ltd.
PRODUCTS:
Discontinued products Ohric* (Sumitomo Chemical).
176
N-3,5-dichlorophenylsuccinimide
1,2-dichloropropane
Insecticide
NOMENCLATURE:
IUPACname 1,2-dichloropropane (I)
Chemical Abstracts name (I) Other names propylene dichloride; PDC
CASRN[78875] ECno2011522 SmilescodeCC(Cl)CCl
PHYSICAL CHEMISTRY: Mol. wt. 113.0 M.f. C3H6Cl2 Form Colourless liquid.
M.p.Freezes 70C B.p. 95.4C V.p. 2.79 107 mPa (19.6C) Kow logP = 2.28 (Agchem.
Desk Ref.) Henry 1.17 103 Pa m3 mol1 (calc.) S.g./density 1.1595 (20C)
Solubility In water 2.7 g/kg (20C). Miscible with ethanol, diethyl ether. Stability Stable
at pH 7 (25C) (Agchem. Desk Ref.) F.p. 21C (Cleveland open cup)
COMMERCIALISATION:
History Its properties as an insecticidal fungicide were described by I. E. Neifert etal. (U.S.
Dep. Agric. Bull., 1925, No. 1313).
APPLICATIONS:
ModeofactionFumigant insecticide. Uses Used in mixture with 1,3-dichloropropene.
Although far less toxic to nematodes (C. R.Youngston & C. I. A. Goring, Plant Dis. Rep., 1970,
54, 196; M.V. McKenry & I. J. Thomason, Hilgardia, 1974, 42, 422) it moves more freely in
soil, from which the greatest loss is by volatilisation (T. R. Roberts & G. Stoydin, Pestic. Sci.,
1976, 7, 325).
ANALYSIS:
Product and residue analysis is by glc. Methods reviewed by J L Daft in Comp. Anal.
Profiles,Chapter11.
EHC 146 (1993). HSG 76 (1992). IARC 41 (1986); 71 (1999). EU Status (1107/2009) Not
approved, Commission Regulation 2076/2002.
IARC Class 3
Inhalation It is strongly narcotic but low concentrations cause an irritation of the
respiratory tract. Exposure of guinea-pigs, rabbits and rats to the vapour has been studied
(L. A. Heppel et al., J. Ind. Hyg.Toxicol., 1946, 28, 1). Water GV 0.04 mg/l (provisional).
Toxicity Class WHO (a.i.) FM ECClassification F; R11| Xn; R20/22
1,2-dichloropropane with 1,3-dichloropropene

NOMENCLATURE:
IUPACname 1,2-dichloropropane +1,3-dichloropropene
Chemical Abstracts name 1,2-dichloropropane +1,3-dichloro-1-propene
1,2-dichloropropane with 1,3-dichloropropene 177

CASRN[8003198] mixture; [78875] 1,2-dichloropropane; [54275

6] 1,3-dichloropropene SmilescodeCC(Cl)CCl.ClC/C=C/Cl;without
stereochemistry:CC(Cl)CCl.ClCC=CCl
PHYSICAL CHEMISTRY:
Composition A mixture of chlorinated hydrocarbons containing 50% m/m (E)- and
(Z)-1,3-dichloropropenes, the other main constituent being 1,2-dichloropropane. It has an
organic chlorine content of 55.0% m/m.
Form Clear amber liquid, with a pungent odour. B.p. Flash distils 59115C V.p. 4.6
10{6} mPa (20C) S.g./density 1.171.22 (20C) Solubility In water c.2 g/kg
(room temperature). Fully miscible with esters, halogenated solvents, hydrocarbons and
ketones. Stability The mixture is stable at 500C but reacts with dilute organic bases,
concentrated acids, halogens and some metal salts. F.p. 17.5C (Abel closed cup)
COMMERCIALISATION:
History Properties as a soil fumigant described by W. Carter (Science, 1943, 97,
383). Introduced by Shell Chemical Co. and by Dow Chemical Co., later replaced by
1,3-dichloropropene.
APPLICATIONS:
ModeofactionFumigant insecticide and nematicide. Uses The mixture is a pre-plant
nematicide effective against soil nematodes including root knot, meadow, sting and dagger,
spiral and sugar beet nematodes. Because the components are highly phytotoxic, a 7-d pre-
planting interval was allowed for every 75 l applied/ha.
PRODUCTS:
Discontinued products DD* (Shell); Vidden D* (Dow).
ANALYSIS:
Product and residue analysis is by glc (T. R. Roberts & G. Stoydin, Pestic. Sci., 1976, 7, 325;
C. E. Castro, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 151; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 710). Methods reviewed by J L Daft in Comp. Anal.
Profiles,Chapter11.
EHC 146 (1993). HSG 76 (1992). EFSA Sci. Rep. (2006) 72, 199. IARC 41 (1986); 71
(1999). EU Status (1107/2009) 1,3-dichloropropene not included, 2007/619/EC.
1,2-dichloropropane and the (Z)-isomer of 1,3-dichloropropene not included, Commission
percutaneous LD50 for rats 779, rabbits 2100 mg/kg. Extremely irritating to the skin and a
severe eye irritant. Also a moderate skin sensitiser. NOEL In 2 y feeding trials, no effects
related to the product were observed in rats receiving 120 mg product/kg diet. Water
GV See individual data for the components.
178
1,2-dichloropropane with 1,3-dichloropropene
ENVIRONMENTAL FATE:
Soil/Environment It does not accumulate in the soil (M.V. McKenry & I. J. Thomason,
Hilgardia, 1974, 42, 393; T. R. Roberts & G. Stoydin, Pestic. Sci., 1976, 7, 325); and has no
permanent harmful effect on soil micro-organisms.
3,4-dichlorotetrahydrothiophene 1,1-dioxide
Nematicide
NOMENCLATURE:
IUPACname 3,4-dichlorotetrahydrothiophene 1,1-dioxide (I)
Chemical Abstracts name (I) Other names dichlorothiolane dioxide
CASRN[3001578] SmilescodeClC1CS(=O)(=O)CC1Cl
PHYSICAL CHEMISTRY: Mol. wt. 189.1 M.f. C4H6Cl2O2S
COMMERCIALISATION:
History Nematicide introduced by Diamond Shamrock Chemical Co. (later Fermenta).
PRODUCTS:
Discontinued products PRD Experimental Nematicide* (Fermenta).
2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate
Chemical Abstracts name 2,2-dichloroethenyl 2-(ethylsulfinyl)ethyl methyl phosphate
CASRN[7076531] DevelopmentcodesNexion 1378 SmilescodeCCS(=O)
CCOP(=O)(OC)OC=C(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 311.1 M.f. C7H13Cl2O5PS
COMMERCIALISATION:
History Insecticide introduced by Celamerck GmbH & Co. (later Shell Agrar GmbH).
APPLICATIONS:
ECClassification T; R23/24/25
2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate 179

dichlozoline
Fungicide
NOMENCLATURE:
Common name dichlozoline (BSI, E-ISO, (f) F-ISO, JMAF, ex ANSI)
IUPACname 3-(3,5-dichlorophenyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione
Chemical Abstracts name 3-(3,5-dichlorophenyl)-5,5-dimethyl-2,4-oxazolidinedione
Other names DDOD CASRN[24201589] DevelopmentcodesCS 8890;
Ortho 8890 SmilescodeCC1(C)OC(=O)N(C1=O)c2ccc(Cl)c(Cl)c2
COMMERCIALISATION:
History Fungicide evaluated by Chevron Chemical Company LLC.
PRODUCTS:
Discontinued products Sclex* (Sumitomo Chemical).
diclobutrazol
Fungicide
Cl
H OH
C C(CH )
3 3
Cl CH2 CH
N
N
N
NOMENCLATURE:
Common name diclobutrazol (BSI, E-ISO, (m) F-ISO)
IUPACname (2RS,3RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)
pentan-3-ol
Chemical Abstracts name (R*,R*)-()--[(2,4-dichlorophenyl)methyl]--(1,1-
dimethylethyl)-1H-1,2,4-triazole-1-ethanol CASRN[75736333] diclobutrazol;
[66345628] unstated stereochemistry ECno2663241 unstated stereochemistry
DevelopmentcodesPP296 SmilescodeCC(C)(C)C(O)C(Cc1ccc(Cl)cc1Cl)n2cncn2
PHYSICAL CHEMISTRY: Mol. wt. 328.2 M.f. C15H19Cl2N3O Form Off-white
crystalline solid. M.p.147149C V.p. 0.0027 mPa (20C) Kow logP = 3.81
Henry 1.25 104 Pa m3 mol1 (calc.) S.g./density 1.25 Solubility In water 7.1 mg/l
180 diclobutrazol
(pH 7, room temperature). In acetone, methanol, ethanol, chloroform <50 g/l. Moderately
soluble in DMF, cyclohexanone, monobutyl ether, and glycol ethers. Slightly soluble in
xylene. Stability Stable to acids and alkalis (pH 414). Also stable to heat (>90 d, 50C),
air, sunlight, and moisture. pKa Basic, pKa <2
COMMERCIALISATION:
History Fungicide reported by K. J. Bent & A. M. Skidmore (Proc. Br. Crop Prot. Conf. - Pests
Dis., 1979, 2, 477). Introduced by ICI Agrochemicals (became Syngenta AG). Patents GB
1595698
APPLICATIONS:
Biochemistry Sterol demethylation (ergosterol biosynthesis) inhibitor.
ModeofactionSystemic fungicide with curative and protective action. Translocated
within the plant predominantly acropetally. Also exhibits vapour action. Uses Control of
rusts on cereals and coffee; and powdery mildews on cereals, vines, apples, and cucurbits.
Phytotoxicity Should not be used on solanaceous crops. Formulation types SC.
PRODUCTS:
Discontinued products Vigil* (Zeneca); Discontinuedmixtures Sopraphal*
(+prochloraz) (Syngenta).
ANALYSIS:
Residues in crops determined by glc with ECD (Pestic. Anal. Man., I, 302).
Oral Acute oral LD50 for rats 4000, mice >1000, guinea pigs 4000, rabbits 4000 mg/kg.
Skin and eye Acute percutaneous LD50 for rats and rabbits >1000 mg/kg. Mild skin and
eye irritant (rabbits). Not a skin sensitiser. NOEL (90 d) for rats 2.5 mg/kg daily; (6 mo)
for dogs 15 mg/kg daily. Other Acute i.p. LD50 for ratsc.500 mg/kg. Toxicity Class WHO
(a.i.) U ECClassification Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >9461 mg/kg. Fish LC50 (24 h) for rainbow trout
23.9 mg/l, (48 h) 15.1 mg/l, (96 h) 9.6 mg/l. Daphnia LC50 (48 h) 9.3 mg/l. Bees LD50 (oral
and contact) 0.05 mg/bee. Worms No adverse effect on earthworm populations 30245
d after application of sprays at 0.2 and 2.0 kg/ha. Other beneficial No adverse effect on
soil microarthropods 30245 d after application of sprays at 0.2 and 2.0 kg/ha.
ENVIRONMENTAL FATE:
Soil/Environment In straw, DT50c.1 week.
diclobutrazol 181
diclomezine
Fungicide
Cl H
N N
CH3 O
Cl
FRAC37, U; pyridazinone fungicide
NOMENCLATURE:
Common name diclom(zine) ((f) F-ISO); diclomezine (BSI, E-ISO)
IUPACname 6-(3,5-dichloro-4-methylphenyl)pyridazin-3(2H)-one
Chemical Abstracts name 6-(3,5-dichloro-4-methylphenyl)-3(2H)-pyridazinone
CASRN[62865365] DevelopmentcodesF-850 (Sankyo); SF-7531 (Sankyo)
SmilescodeCc1c(Cl)cc(cc1Cl)c2ccc(=O)[nH]n2
PHYSICAL CHEMISTRY: Mol. wt. 255.1 M.f. C11H8Cl2N2O Form Colourless crystals.
M.p.250.5253.5C V.p. <1.3 10-2 mPa (60C) Solubility In water 0.74 mg/l (25C).
In methanol 2.0, acetone 3.4 (both in g/l, 23C). Stability Slowly decomposed by sunlight.
Stable under acidic, neutral, and alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by Y. Takahi (Jpn. Pestic. Inf., 1988, No. 52, p. 31). Introduced
in Japan (1988) by Sankyo Co., Ltd (agrochemicals interests now Mitsui Chemicals Inc.).
Patents US 4052395; GB 1533010; JP 1170243 Manufacturers Mitsui Chemicals Agro;
Sankyo Agro
APPLICATIONS:
ModeofactionFungicide with curative and protective action. Inhibits septum formation
and mycelial growth. Uses Control of Rhizoctonia and Sclerotium spp. in rice; white
mould and twig rot on peanuts; and Rhizoctonia disease of turf. Applied at 360480 g/ha.
Formulation types DP; SC. WP.
PRODUCTS:
Other mixtures Rabu-Monguard-Jorker (+phthalide +silafluofen) (Hokko);
Discontinued products Monguard* (Sankyo Agro).
ANALYSIS:
Product analysis by hplc. Residues determined by glc of a derivative.
rats >5000 mg/kg. Not a skin irritant. Inhalation LC50 (4 h) for rats 0.82 mg/l.
NOEL (2 y) for male rats 98.9, female rats 99.5 mg/kg daily. Other Non-mutagenic and
non-teratogenic. Toxicity Class WHO (a.i.) U.
182 diclomezine
ECOTOXICOLOGY:
Birds Dietary LC50 for bobwhite quail and mallard ducks >7000 ppm. Dietary LD50 for
bobwhite quail >3000 mg/kg. Fish LC50 (48 h) for carp >300 mg/l. Daphnia LC50 (5 h)
>300 mg/l. Bees LD50 (oral and contact) for honeybees >100 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment Readily adsorbed on soil particles.
dicyclonon
Herbicide safener
Cl N
Cl
O
NOMENCLATURE: (RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one
Common name dicyclonone ((f) F-ISO);

Caution: dicyclonon
Stereochemical (BSI,s E-ISO)
terms discarded:
IUPACname (RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-
one (RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one
Chemical Abstracts name 1-(dichloroacetyl)hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]

pyrimidin-6(2H)-one CASRN[79260712]; [110499257] (R)- isomer; [110499279]
(S)- isomer; the substance named dicyclonon in Chemical Abstracts Registry, with Registry
Number [85072828], is actually an isomer of dicyclonon, with a methyl group in position
7 instead of at the bridgehead position 8a. DevelopmentcodesBAS 145138 (BASF)
COMMERCIALISATION:
Manufacturers BASF
APPLICATIONS:
herbicide, and its subsequent conjugation (see J. Davies & J. C. Caseley, Pestic. Sci. 1999,
55(11) 10431058). Uses Can be used to safen maize to a wide variety of herbicides.
dicyclonon 183
dicyclopentadiene
Animal repellent
NOMENCLATURE:
IUPACname 3a,4,7,7a-tetrahydro-1H-4,7-methano-indene
Chemical Abstracts name 3a,4,7,7a-tetrahydro-4,7-methano-1H-indene CASRN[77
736] SmilescodeC1C=CC2C3CC(C=C3)C12
PHYSICAL CHEMISTRY: Mol. wt. 132.2 M.f. C10H12 Form Colourless crystals.
M.p.32.7C B.p. 64.5C /14mm Hg V.p. 0.33 mPa (25C) S.g./density 0.9766 (33C)
Solubility Sparingly soluble in water. Readily soluble in acetone, dichloromethane, ethyl
acetate, hexane, and toluene. Stability Chemically very stable.
COMMERCIALISATION:
History Animal repellent introduced by Staehler.
APPLICATIONS: Uses As a repellent for animals such as hares, rabbits, and deer,
in winter or in summer. Applied in the form of impregnated strips on deciduous and
coniferous trees, or by spraying around ornamental plants and shrubs. Normally used in
combination with other materials. Formulation types SC.
ANALYSIS:
Product by glc with FID.
ICSC.873 (2005). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
rabbits 6720 mg/kg. Mild skin and eye irritant (rabbits). Inhalation LC50 (4 h) for rats 660
mg/l air.
ECOTOXICOLOGY:
Fish LC50 (96 h) for carp 62.2, rainbow trout 22.86 mg/l. Bees Not toxic to bees.
184 dicyclopentadiene
dieldrin
Insecticide
IRAC2A
NOMENCLATURE:
Common name HEOD (for pure compound) (BSI, E-ISO, F-ISO, JMAF); dieldrine ((f)
F-ISO); dieldrin (USSR before 1984, Denmark); dieldrin (material containing >85% HEOD)
(BSI, E-ISO, BAN, ESA, JMAF, except Denmark)
IUPACname (1R,4S,4aS,5R,6R,7S,8S,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-
octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
Chemical Abstracts name (1a,2,2a,3,6,6a,7,7a)-3,4,5,6,9,9-hexachloro-
1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene
CASRN[60571] ECno2004845 DevelopmentcodesCompound 497 (to
Hyman) SmilescodeClC1=C(Cl)C2(Cl)C3C4CC(C5OC54)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 380.9 M.f. C12H8Cl6O Form Tech. consists of buff
to light tan flakes with a mild odour. M.p.175176C; (tech. sets at >95C) V.p. 0.4 mPa
(20C) Henry 8.19 101 Pa m3 mol1 (calc.) S.g./density 1.62 (20C) Solubility In
water 0.186 mg/l (20C). Stability Stable to alkali, mild acids and to light. It reacts with
concentrated mineral acids, acid catalysts, acid oxidising agents and active metals (iron,
copper).
COMMERCIALISATION:
History Insecticide reported by C. W. Kearns etal. (J. Econ. Entomol., 1949, 42, 127).
Introduced by J. Hyman & Co. and later by the Shell International Chemical Co., Ltd.
Patents US 2676547
APPLICATIONS:
ModeofactionContact and ingested insecticide. Uses A presistent insecticide, used to
control locusts and tropical disease vectors, such as Glossina spp. Industrial uses included
timber preservation, termite-proofing of plastic and rubber coverings of electrical and
telecommunication cables, of plywood and building boards and as a termite barrier in
building construction. Formulation types EC; GR; WP.
PRODUCTS:
Discontinued products Octalox* (Hyman).
ANALYSIS:
Product analysis by glc, by i.r. spectrophotometry (CIPACHandbook, 1983, 1B, 1780;
FAO Specification (CP/36), Organochlorine Insecticides 1973; AOACMethods 18th Ed.,
961.05), by tlc (ibid., 972.05), or by potentiometric titration of liberated chloride ion
(CIPACHandbook, 1994, F, 190). Residues determined by glc, tlc or paper chromatography
(AOACMethods, 18th Ed., 970.52; ibid., 985.22), or by glc with ECD (Anal. Methods Pestic.
Plant Growth Regul., 1972, 6, 268; Analyst (London), 1979, 104, 425; P. A. Greve & W. B. F.
dieldrin 185
Grevenstuk, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1115; G. M. Telling et al., J.
Chromatogr., 1977, 137, 405; M. A. Luke et al., J. Assoc. Off. Anal. Chem., 1981, 64, 1187; ibid.,
1985, 68, 385, 29.A0129.A04). See also Pestic. Anal. Man., I, 204, 208, 301, 302, 303, 304, 402,
502. In drinking water by glc with ECD (AOACMethods, 18th Ed., 990.06).
EHC 91 (1989). JMPR Mtg. 65 (1992); JMPR Evaln. 29 (1977). HSG 21 (1989). PDS 17 (1975).
ICSC.787 (1998). IARC 5 (1974); Suppl. 7 (1987). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EC, as amended by
IARC Class 3
Oral Acute oral LD50 for rats 3787, rabbits 4550 mg/kg. Skin and eye Acute
percutaneous LD50 for rats 6090 mg/kg. NOEL In long-term exposure, NOEL for rats
and dogs 0.1 mg/kg diet (0.005 mg/kg daily). Data available indicate that dieldrin and aldrin
do not produce malignant tumours in rats, dogs, monkeys at all tolerated dose levels in
long-term feeding studies. The significance of the marginal increase in incidence of hepatic
tumours in mice, following lifetime exposure to dieldrin, is doubtful. ADI/RfD (JMPR)
0.0001 mg (total aldrin +dieldrin)/kg b. w. (PTDI) [1994]; (EPA) cRfD 0.00005 mg/kg b.w.
[1990]. Water GV 0.03 ;g/l (sum of aldrin+dieldrin). Toxicity Class WHO (a.i.) Ib
ECClassification T+; R27| T; R25, R48/25| R40| N; R50, R53 PIC Yes.
ENVIRONMENTAL FATE:
Animals Oxidised in the liver to a hydrophilic hydroxy compound, and is subsequently
eliminated in the urine as the glucuronic acid conjugate.
dienochlor
Acaricide
Cl Cl
Cl Cl
Cl
Cl Cl
Cl
Cl Cl
NOMENCLATURE:
Common name dienochlor (BSI, E-ISO); di(nochlore) ((m) F-ISO)
IUPACname perchloro-1,1-bicyclopenta-2,4-diene
Chemical Abstracts name 1,1,2,2,3,3,4,4,5,5-decachlorobi-2,4-cyclopentadien-1-yl
CASRN[2227170] DevelopmentcodesSAN 804 I SmilescodeClC1=C(Cl)C(Cl)
(C(=C1Cl)Cl)C2(Cl)C(=C(Cl)C(=C2Cl)Cl)Cl
186 dienochlor
PHYSICAL CHEMISTRY: Mol. wt. 474.6 M.f. C10Cl10 Form Grey crystals; (tech.,
light yellow powder, sometimes with faint onion or garlic odour). M.p.122123C; (tech.,
111128C) B.p. 250C (decomp.) V.p. 0.29 mPa (extrapolated to 25C) Kow logP =
3.23 (mean, 25C) S.g./density 1.923 (tech., 25C) Solubility Practically insoluble
in water (25 ppb). In iso-octane 7.89, toluene 59.00, acetonitrile 1.16, n-octanol 4.77,
tetrahydrofuran 98.32 (all in g tech./100 ml). Stability Tech. dienochlor was stable when
stored at 54C for 14 d, and at 42C for 2 y. Hydrolysis DT50 (25C) 30.5 d (pH 9), 93 d
(pH 7), 184 d (pH 5). DT50 as thin film solution in simulated sunlight 1.6 min.
COMMERCIALISATION:
History Acaricide reported by W. W. Allen etal. (J. Econ. Entomol., 1964, 57, 187).
Introduced by Hooker Chemical Corp. and later by Zoecon Corp., followed by Sandoz
AG (later Novartis Crop Protection AG). Patents US 2732409; US 2934470 (to Hooker)
Manufacturers Novartis
APPLICATIONS:
ModeofactionAcaricide with predominantly contact action. Interferes with oviposition.
Long residual activity under glasshouse conditions. Uses Control of mites (Tetranychus
spp., Panonychus ulmi, and Polyphagotarsonemus latus) on roses, chrysanthemums, and other
ornamentals, normally under glass. Formulation types WP; EW .
PRODUCTS:
Discontinued products Pentac* (Novartis); Pentac Aquaflow* (Dow).
ANALYSIS:
Product analysis by hplc spectroscopy. Residues determined by hplc. In soil, by gc/ECD
(Environ. Chem. Methods).
Oral Acute oral LD50 for male albino rats >3160 mg tech./kg. Skin and eye Acute
percutaneous LD50 for rabbits >3160, rats >2000 mg/kg. Mildly irritating to eyes and skin
(rabbits). Sensitising to skin. Inhalation LC50 (4 h) for rats 0.08 mg/l air.
Toxicity Class WHO (a.i.) III EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 4319 mg/kg. Dietary LC50 (8 d) for mallard ducks
3966, bobwhite quail >5620 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.050, bluegill
sunfish 0.6 mg/l. Daphnia LC50 (48 h) 1.2 mg/l. Algae NOEC (96 h) for Scenedesmus
subspicatus >30 mg/l. Bees LD50 (contact) >36 g/bee. Worms LC50 (7d and 14 d) >1000
mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals Rapid degradation was observed in rats. Within 4 days, following a single oral
dose of 1 mg/kg, female rats excreted 2% and 88% of applied 14C in urine and faeces
dienochlor 187
respectively. Plants Major degradation products are perchloroketones. Degradation is

mainly photochemical rather than metabolic; DT50 23 d when plants are exposed to
sunlight. Soil/Environment Soil adsorption Kd 384 (silty loam, pH 6.1, 3.6% o.m.), 196
(loamy sand, pH 7.5, 0.5% o.m.), 269 (silty clay loam, pH 6.8, 11.8% o.m.), 311 (sandy loam,
pH 6.9, 1.3% o.m.). In soil DT50 3.1 d.
diethamquat; diethamquat dichloride

Herbicide
NOMENCLATURE:
Common name diethamquat (BSI, E-ISO, (m) F-ISO)
IUPACname 1,1-bis(diethylcarbamoylmethyl)-4,4-bipyridinium
Chemical Abstracts name 1,1-bis[2-(diethylamino)-2-oxoethyl]-4,4-bipyridinium
CASRN[4029021] dichloride, formerly [111156457]; [400852677] dication
DevelopmentcodesPP831
PHYSICAL CHEMISTRY: Mol. wt. 384.5; (diethamquat dichloride 455.4)
M.f. C22H32N4O2; (diethamquat dichloride C22H32Cl2N4O2)
COMMERCIALISATION:
History Dichloride evaluated as herbicide by ICI Plant Protection Division (later ICI
Agrochemicals).
diethatyl-ethyl; diethatyl
Herbicide
NOMENCLATURE:
Common name (for the acid) diethatyl (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname (acid) N-chloroacetyl-N-(2,6-diethylphenyl)glycine
Chemical Abstracts name (acid) N-(chloroacetyl)-N-(2,6-diethylphenyl)glycine
CASRN[38727558] ethyl ester; [38725950] acid Developmentcodes(acid)
Hercules 22 234 Smilescodeacid:CCc1cccc(CC)c1N(CC(=O)O)C(=O)
CCl;ester:CCOC(=O)CN(C(=O)CCl)c1c(CC)cccc1CC
PHYSICAL CHEMISTRY: Mol. wt. 311.8; (acid 283.8) M.f. C16H22ClNO3 (ester);
C14H18ClNO3 (acid) Form Colourless crystals. M.p.4950C V.p. 0.43 mPa (30C)
Kow logP = 3.599 (pH 6.6, 25C) S.g./density 1.38 (25C) Solubility In water 105 mg/l
(25C). In methanol, ethanol 810, isopropanol 750, acetone, xylene 820, methyl isobutyl
ketone 830, chloroform 770, kerosene 200 (all in g/kg, room temperature).
Stability Hydrolysed under strongly acidic or alkaline conditions. Thermally stable up to
240C. Tech. and formulations are stable for >2 y under normal conditions.
188 diethatyl-ethyl; diethatyl

COMMERCIALISATION:
History Herbicidal activity of the ethyl ester reported by S. K. Lehman (Proc. North Cent.
Weed Control Conf., 29th, 1972); introduced by Hercules Inc. Agrochemicals (later Nor-Am
Chemical Co.).
Manufacturers NOR-AM
APPLICATIONS:
Biochemistry Inhibits cell division by blocking protein synthesis. It is reported that
chloroacetamides inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr.
Meeting WSSA,Toronto, 40, 117118, 2000; P. Bger, Abstr. III Int.Weed Control Congr., Brazil,
2000). ModeofactionSelective soil-herbicide, absorbed primarily by the emerging
shoots, and secondarily by the roots. Uses Pre-plant soil-incorporated or pre-emergence
control of annual grasses and some broad-leaved weeds in sugar beet, soya Beans, cotton,
sunflowers, potatoes, peanuts, phaseolus beans, fodder beet, beetroot, sugar cane, flax,
spinach, wheat, rice, and other crops at rates in the range 2.26.7 kg/ha.
PRODUCTS:
Discontinued products Antor* (diethatyl-ethyl) (AgrEvo).
ANALYSIS:
Product analysis by glc or hplc. Residues determined by glc.
4118 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >4000 mg/kg. Mild skin
and eye irritant (rabbits). NOEL (2 y) for rats and mice 1000 mg/kg diet, for dogs
50 mg/kg diet. In 3-generation study, NOEL for rats 200 mg/kg diet.
ECOTOXICOLOGY:
Birds Diethatyl-ethyl: acute oral LD50 for mallard ducks and bobwhite quail >10000 mg/
kg. Fish LC50 (24 h) for bluegill 7.14 mg/l (NOEL 2.4 mg/l), for rainbow trout 10.3 mg/l
(NOEL 1.0 mg/l). LC50 (96 h) for bluegill sunfish 3.34, rainbow trout 1.82 mg/l. Bees Not
toxic to bees at 43.5 g/bee.
ENVIRONMENTAL FATE:
Plants In plants, diethatyl is rapidly metabolised (almost completely within 4 days), with
translocation of metabolites throughout the plant. Soil/Environment In soil, micro-
organisms appear to play a significant role in degradation. Residual activity persists for
c.610 weeks.
diethatyl-ethyl; diethatyl 189

dietholate
Herbicide safener
NOMENCLATURE:
Common name dietholate (WSSA)
IUPACname O,O-diethyl O-phenyl phosphorothioate (I)
Chemical Abstracts name (I) CASRN[32345292] DevelopmentcodesR 33865
APPLICATIONS:
Biochemistry Appears to act by inhibiting metabolism of the carbonyl linkage of EPTC
(T. B. Moorman et al., Soil Biol. Biochem., 1992, 24(2) 121). Uses Inhibits degradation of
thiocarbamate herbicides, in soils with high microbial activity. Also acts as an insecticide
synergist. (R. M. Hollingworth et al., Pure & Appl. Chem., 1995, 67, 14871532).
PRODUCTS:
Discontinuedmixtures Eradicane Extra* (+dichlormid +EPTC) (Zeneca).
O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(6-methyl-2-propyl-4-pyrimidinyl)
phosphorothioate CASRN[5826915] DevelopmentcodesG 24 622
SmilescodeCCCc1nc(C)cc(OP(=S)(OCC)OCC)n1
COMMERCIALISATION:
History Insecticide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrazinon* (Ciba-Geigy).
diethyl 5-methylpyrazol-3-yl phosphate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname diethyl 5-methylpyrazol-3-yl phosphate
190
diethyl 5-methylpyrazol-3-yl phosphate
Chemical Abstracts name diethyl 5-methyl-1H-pyrazol-3-yl phosphate

Other names pyrazoxon CASRN[108349] DevelopmentcodesG 24 483
SmilescodeCCOP(=O)(OCC)Oc1cc(C)[nH]n1
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrazoxon* (Ciba-Geigy).
ECClassification T+; R26/27/28
O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate

Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate; O,O-
diethyl O-4-methylcoumarin-7-yl phosporothioate; 7-diethoxyphosphinothioyloxy-4-
methylcoumarin
Chemical Abstracts name O,O-diethyl O-(4-methyl-2-oxo-2H-1-benzopyran-7-
yl) phosphorothioate CASRN[299456] DevelopmentcodesE 838 (Bayer)
SmilescodeCCOP(=S)(OCC)Oc1ccc2c(C)cc(=O)oc2c1
COMMERCIALISATION:
History Insecticide reported by G. Schrader (Angew. Chem., 1952, Monogr. No. 62, 2nd Ed.).
Introduced by Bayer AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionIngested insecticide. Uses For
use against colorado beetle.
PRODUCTS:
Discontinued products Potasan* (Bayer); Discontinuedmixtures Potasan G*
(+gamma-HCH) (Bayer).
ECClassification T+; R26/27/28| N; R50, R53| concn. dep.
O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate 191

difenopenten; difenopenten-ethyl
Herbicide
NOMENCLATURE:
Common name dif(nopent) ((m) F-ISO); difenopenten (BSI, E-ISO, ANSI, WSSA)
IUPACname (E)-()-4-[4-(,,-trifluoro-p-tolyloxy)phenoxy]pent-2-enoic acid
Chemical Abstracts name (E)-()-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-2-
pentenoic acid CASRN[81416446] difenopenten; [71101058] difenopenten-ethyl
DevelopmentcodesXE-773; KK-80 (both for difenopenten-ethyl)
PHYSICAL CHEMISTRY: Mol. wt. 352.3; (ethyl ester 380.4) M.f. C18H15F3O4; (ethyl
ester C20H19F3O4)
COMMERCIALISATION:
History Herbicide evaluated by Chevron Chemical Company LLC.
difenoxuron
Herbicide
CH3O O NHCON(CH3)2
NOMENCLATURE:
Common name difenoxuron (BSI, E-ISO, (m) F-ISO)
IUPACname 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea
Chemical Abstracts name N-[4-(4-methoxyphenoxy)phenyl]-N,N-
dimethylurea CASRN[14214325] DevelopmentcodesC 3470
SmilescodeCOc1ccc(Oc2ccc(NC(=O)N(C)C)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 286.3 M.f. C16H18N2O3 Form Colourless crystals.
M.p.138139C V.p. 1.24 106 mPa (20C) Henry 1.78 10-8 Pa m3 mol1 (calc.)
S.g./density 1.30 (20C) Solubility In water 20 mg/l (20C). In dichloromethane 156,
acetone 63, isopropanol 10, benzene 8, hexane 0.05 (all in g/kg, 20C). Stability No
significant hydrolysis occurs at 30C and pH 1 or 13.
COMMERCIALISATION:
History Herbicide reported by L. Ebner & J. Schuler (Proc. Br.Weed Control Conf., 7th, 1964,
2, 711). Introduced by Ciba-Geigy AG. Patents BE 593743; GB 913383
APPLICATIONS:
site. ModeofactionSelective herbicide, absorbed by the leaves and roots. Uses Control
192 difenoxuron
of annual broad-leaved weeds post-emergence in onions, leeks, garlic, and other alliums at
2.5 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products Lironion* (Ciba-Geigy).
ANALYSIS:
Product analysis by acidimetric titration. Residues determined by glc.
for rats >2150 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 (6 h) for
rats >0.66 mg/l air. NOEL (90 d) for rats 50 mg/kg daily, for dogs 200 mg/kg daily.
ECOTOXICOLOGY:
Fish LC50 (48 h) for trout 510 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50c.12 d.
dihydroazadirachtin
Insecticide
O
C CO2CH3
CH3
O O OH O
CH3 CH3
HO
O CH3O
O
CH3C O OH
H
CH3OC O
O
NOMENCLATURE:
Chemical Abstracts name 22,23-dihydroazadirachtin; dimethyl [2aR-[2a,3,4(1aR*,2
S*,3aR???*,6aS*,7S*,7aS*),4a, 5,7aS*,8(E),10,10a,10b]]-10-(acetyloxy)-4-(hexahydro-
6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl)octahydro-3,5-
dihydroxy-4-methyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-1H,7H-naphtho[1,8-bc:4,4a-c]
difuran-5,10a(8H)-dicarboxylate CASRN[108189588]; [37324451] (unspecified
stereochemistry)
dihydroazadirachtin 193

APPLICATIONS:
Biochemistry Ecdysone antagonist. Uses For control of ants, aphids, Beetles, caterpillars,
crickets, etc, on horticultural and ornamental plants. Formulation types WG .
Oral Acute oral LD50 for rats >5 g/kg. Skin and eye Acute percutaneous LD50 for
rabbits >2 g/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea
pigs). Inhalation LC50 for rats >2.9 mg/l. Other Non-mutagenic in reverse mutation,
unscheduled DNA synthesis and CHO tests.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >816 mg/kg. Dietary LD50 for bobwhite quail
>1875 mg/kg. Fish LD50 (96 h) for rainbow trout 17.65, bluegill sunfish 9 mg/kg.
Daphnia LD50 11.6 mg/l Bees Relatively non-toxic to honeybees.
2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
NOMENCLATURE:
IUPACname 2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
Chemical Abstracts name 2,3-dihydro-5,6-diphenyl-1,4-oxathiin
CASRN[58041193] DevelopmentcodesP 293 SmilescodeC1CS/C(=C(\O1)/
c2ccccc2)/c3ccccc3;without stereochemistry:C1CSC(=C(O1)c2ccccc2)c3ccccc3
PHYSICAL CHEMISTRY: Mol. wt. 254.4 M.f. C16H14OS
COMMERCIALISATION:
History Plant growth regulator evaluated by Uniroyal Chemical Co., Inc.
2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Fungicide
NOMENCLATURE:
IUPACname 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Chemical Abstracts name 2,3-dihydro-5-phenyl-1,4-dithiin 1,1,4,4-tetraoxide
CASRN[34407879] DevelopmentcodesP 368
SmilescodeO=S/1(=O)CCS(=O)(=O)/C(=C1)/c2ccccc2;without
stereochemistry:O=S1(=O)CCS(=O)(=O)C(=C1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 258.3 M.f. C10H10O4S2
COMMERCIALISATION:
History Fungicide evaluated by Uniroyal Chemical Co., Inc.
194
2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
dimefox
IRAC1B
NOMENCLATURE:
Common name dimefox (BSI, E-ISO, (m) F-ISO)
IUPACname tetramethylphosphorodiamidic fluoride (I)
Chemical Abstracts name (I) Other names DMF CASRN[115264]
ECno2040768 SmilescodeCN(C)P(=O)(F)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. contains schradan (q.v.) and tris(dimethylamino)phosphine oxide.
Mol. wt. 154.1 M.f. C4H12FN2OP Form Colourless liquid. B.p. 67C /4 mmHg
V.p. 48000 mPa (25C) Kow logP = 1.2 (chloroform/water) S.g./density 1.115 (20C)
Solubility Miscible with water and most organic solvents. Stability Resistant to
hydrolysis by alkali but is hydrolysed by acids. Slowly oxidised by vigorous oxidising agents,
rapidly by chlorine.
COMMERCIALISATION:
History Insecticide and acaricide reported by H. Kkenthal & G. Schrader (B.I.O.S. Final
Report, 1946, 1095). Introduced by Fisons Pest Control Ltd (later Schering Agrochemicals).
Patents GB 688760, GB 741662.
APPLICATIONS:
acaricide. Uses As a soil treatment for hop plants against aphids and red spider mites.
Effective for 4256 d.
PRODUCTS:
Discontinued products PestoxXIV* (Fisons); TerraSytol* (DuPont);
Discontinuedmixtures Sytam* (+schradan) (with tris(dimethylamino)phosphine
oxide) (Murphy, Wacker); Terra Sytam* (+schradan) (with tris(dimethylamino)phosphine
oxide) (Murphy, Wacker).
ANALYSIS:
Product analysis, see CIPACHandbook, 1980, 1A, 329; mixture with schradan, ibid., 334.
Oral Acute oral LD50 for rats 12 mg/kg. Toxicity Class WHO (a.i.) Ia
ECClassification T+; R27/28
dimefox 195
dimethipin
Herbicide, plant growth regulator
O O
CH3 S
CH3 S
O O
NOMENCLATURE:
Common name no name (Japan); dimethipin (BSI, ANSI, E-ISO); dim(thipin) ((m) F-ISO)
IUPACname 2,3-dihydro-5,6-dimethyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Chemical Abstracts name 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetraoxide
CASRN[55290647] DevelopmentcodesN 252
SmilescodeCC1=C(C)S(=O)(=O)CCS1(=O)=O
PHYSICAL CHEMISTRY: Mol. wt. 210.3 M.f. C6H10O4S2 Form Tech. is a white,
crystalline solid. M.p.167169C V.p. 0.051 mPa (25C) Kow logP = 0.17 (24C)
Henry 2.33 106 Pa m3 mol1 (calc.) S.g./density 1.59 g/cm3 (23C) Solubility In
water 4.6 g/l (25C). In acetonitrile 180, methanol 10.7, toluene 8.979 (all in g/l, 25C).
Stability Stable at pH 3, 6 and 9 (25C). Stable for 1 y at 20C, 14 d at 55C. Stable to
light 7 d at 25C. pKa 10.88, v. weak acid
COMMERCIALISATION:
History Plant growth regulator reported by R. B. Ames etal. (Proc. Beltwide Cotton
Produc. Res. Conf., 1974, p. 61). Introduced by Uniroyal Chemical Co., Inc. (became
Chemtura Corp.) in USA in 1982. Patents US 3920438 Manufacturers Chemtura
APPLICATIONS:
Biochemistry Interferes with protein synthesis in the plant epidermis.
ModeofactionDefoliant and desiccant. Uses Defoliation of cotton, nursery stock,
rubber trees, and vines, at 260720 g/ha. Potato haulm desiccant, at 480720 g/ha. Reduces
seed moisture content at harvest of maize, rice, oilseed rape, flax, and sunflowers, at
240720 g/ha. Formulation types SC.
PRODUCTS:
Discontinued products Harvade* (Chemtura); Lintplus* (Chemtura);
Discontinuedmixtures Leafless* (+thidiazuron) (Chemtura).
ANALYSIS:
Product analysis by glc or i.r. spectrometry. Residues determined by gc/S-FPD (Resid. Anal.
Methods). See also Pestic. Anal. Man., II, 180.406, 186.2050. Details available from Chemtura.
JMPR Mtg. 101 (2004); JMPR Evaln. I 93 (2001); JMPR Evaln. II 88 (1999), 104 (2004).
196 dimethipin
rabbits >5000 mg/kg. Extreme eye irritant; not a dermal irritant (rabbits). Weak sensitiser
(guinea pigs). Inhalation LC50 (4 h) for rats 1.2 mg/l. NOEL In chronic feeding studies,
NOEL for rats 2, dogs 25 mg/kg b.w. daily. ADI/RfD (JMPR) 0.02 mg/kg b.w. [1999, 2004];
(EPA) cRfD 0.02 mg/kg b.w. [1990, 2005]. Toxicity Class WHO (a.i.) III EPA (formulation)
I (tech.), III (Harvade 5F and Harvade 25F)
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 ppm. LC50 for
mallard ducks 896 mg/kg. Fish LC50 (96 h) for rainbow trout 52.8, bluegill sunfish 20.9,
sheepshead minnows 17.8 mg/l. Daphnia LC50 (48 h) 21.3 mg/l. Algae EC50 (5 d) for
Selenastrum capricornutum 5.12 mg/l. Other aquatic spp. LC50 (96 h) for mysid shrimps
(Mysidopsis bahia) 13.9 mg/l. Bees LD50 >100 g/bee (25% formulation). Worms LC50
(14 d) for earthworms >39.4 ppm (25% formulation).
ENVIRONMENTAL FATE:
Plants Unchanged. Soil/Environment DT50 in soilc.104149 d. Kd 0.092; Koc 3.27.
dimethirimol
Fungicide
CH3 N N(CH3)2
N
CH3(CH2)3
OH
FRAC8, A2
NOMENCLATURE:
Common name dimethirimol (BSI, E-ISO, JMAF); dim(thyrimol) ((m) F-ISO)
IUPACname 5-butyl-2-dimethylamino-6-methylpyrimidin-4-ol
Chemical Abstracts name 5-butyl-2-(dimethylamino)-6-methyl-4(1H)-pyrimidinone
CASRN[5221534] DevelopmentcodesPP675 (ICI)
SmilescodeCCCCc1c(C)nc(nc1O)N(C)C
M.p.102C V.p. 1.46 mPa (30C) Kow logP = 1.9 Henry <2.55 104 Pa m3 mol1 (25C,
calc.) Solubility In water 1.2 g/l (25C). Readily soluble in aqueous solutions of strong
acids. In chloroform 1200, xylene 360, ethanol 65, acetone 45 (all in g/l, 25C).
Stability Stable in acidic and alkaline solutions. Decomposed by sunlight when in aqueous
solution; DT50c.7 d. Dissolves in aqueous solutions of strong acids to form water-soluble
salts.
dimethirimol 197
COMMERCIALISATION:
History Systemic fungicide reported by R. S. Elias etal. (Nature (London), 1968, 219, 1160).
Introduced by ICI Plant Protection Division (later Syngenta AG) and first marketed in 1970.
Patents GB 1182584 Manufacturers Syngenta
APPLICATIONS:
Biochemistry Inhibits nucleic acid synthesis (adenosine deaminase).
ModeofactionSystemic fungicide with protective and curative action. Absorbed by
the roots, with translocation in the xylem. Uses Soil application for control of powdery
mildews in cucurbits, tobacco, capsicums, tomatoes, and some ornamentals, at 0.52 kg/ha;
also as a foliar spray at 50100 g/ha.. Formulation types SL .
PRODUCTS:
Discontinued products Milcurb* (Syngenta).
ANALYSIS:
Product analysis by glc (J. E. Bagness & W. G. Sharples, Analyst (London), 1974, 99, 225).
Residues determined by hplc.
Oral Acute oral LD50 for rats 2350, mice 8001600, guinea pigs 500 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >400 mg/kg. Non-irritating to skin and
eyes (rabbits). NOEL (2 y) for dogs 25 mg/kg, for rats 300 mg/kg diet. Other Acute i.p.
LD50 for rats 200400 mg/kg. Toxicity Class WHO (a.i.) U EPA (formulation) III
ECClassification (Xn; R21)
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 4000 mg/kg. Fish LC50 (24 h) for young brown trout
42 mg/l, (48 h) 33 mg/l, (96 h) 28 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, metabolism involves demethylation of the dimethylamino group.
Soil/Environment Soil DT50c.120 d (sandy soil, glasshouse and John Innes composts).
dimethrin
Insecticide
IRAC3
NOMENCLATURE:
Common name dimethrin (BSI, E-ISO, ANSI); dim(thrine) ((f) F-ISO)
IUPACname 2,4-dimethylbenzyl (1RS)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-
enyl)cyclopropanecarboxylate; 2,4-dimethylbenzyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-
3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 2,4-dimethylbenzyl ()-cis-trans-
chrysanthemate
198 dimethrin
Chemical Abstracts name (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-

propenyl)cyclopropanecarboxylic acid CASRN[70382] unstated stereochemistry
SmilescodeCC(=CC1C(C(=O)OCc2ccc(C)cc2C)C1(C)C)C
COMMERCIALISATION:
History Insecticide synthesised by W. F. Barthel, activity reported by P. G. Piquett & W. A.
Gersdorff (J. Econ. Entomol., 1958, 51, 791).
APPLICATIONS:
JMPR Evaln. 4 (1965).
NOEL (1 y) for rats 300 mg/kg b.w. (EPA Tracking). ADI/RfD (JMPR) No ADI [1965];
(EPA) 0.3 mg/kg b.w. [1986].
2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (I)
Chemical Abstracts name (I) CASRN[7122045] DevelopmentcodesC 10 015
SmilescodeCNC(=O)Oc1ccccc1C2OC(C)C(C)O2
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., 1968 Suppl.,
p. 39). Introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
insecticide.
PRODUCTS:
Discontinued products Fondaren* (Ciba-Geigy); Sapecron C* (Ciba).
2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate 199

5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
Chemical Abstracts name 5,5-dimethyl-3-oxo-1-cyclohexen-1-yl
dimethylcarbamate Other names dimetan CASRN[122156] ECno2045258
DevelopmentcodesG 19 258 SmilescodeCN(C)C(=O)OC1=CC(=O)CC(C)(C)C1
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Dimetan* (Geigy).
ECClassification T; R25
dimetilan
Insecticide
NOMENCLATURE:
Common name dimetilan (BSI, ESA)
IUPACname 1-dimethylcarbamoyl-5-methylpyrazol-3-yl dimethylcarbamate
Chemical Abstracts name 1-[(dimethylamino)carbonyl]-5-methyl-1H-pyrazol-3-yl
dimethylcarbamate CASRN[644644] ECno2114200 DevelopmentcodesG 22
870; GS 13 332 SmilescodeCN(C)C(=O)Oc1cc(C)n(n1)C(=O)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. is >96%. Mol. wt. 240.3 M.f. C10H16N4O3 Form Colourless solid;
(tech. is a light yellow to reddish-brown crystalline solid). M.p.6871C; (tech., 55
65C) B.p. 200210/13 mmHg V.p. 13 mPa (20C) Solubility Readily soluble in water,
chloroform, DMF; soluble in ethanol, acetone, xylene and other organic solvents.
Stability Hydrolysed by acids and by alkalis.
COMMERCIALISATION:
History Insecticide reported by H. Gysin (Chimia, 1954, 8, 205, 221). Introduced by J.
R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 281946, CH 282655, GB 681376, US
2681879.
200 dimetilan
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionIngested insecticide. Uses For
control of flies.
PRODUCTS:
Discontinued products Snip* (Ciba-Geigy).
ANALYSIS:
Product analysis is by glc with internal standard. Residues may be determined by glc with
MCD or by tlc. See also A. Margo & K. Stammbach, Anal. Methods Pestic. Plant Growth Regul.
Food Addit., 1964, 2, 183; Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 376.
Oral Acute oral LD50 for rats 64, mice 6065 mg/kg. Livestock is more susceptible.
Toxicity Class WHO (a.i.) Ib ECClassification T; R25| Xn; R21| N; R50, R53
dimexano
NOMENCLATURE:
Common name dimexano (BSI (from 1984), E-ISO, (m) F-ISO); dimexan* (BSI before
1984)
IUPACname O,O-dimethyl dithiobis(thioformate)
Chemical Abstracts name dimethyl thioperoxydicarbonate
Other names dimethylxanthic disulfide CASRN[1468377] ECno2159938
SmilescodeCOC(=S)SSC(=S)OC
PHYSICAL CHEMISTRY:
Composition Tech. isc.96%. Mol. wt. 214.3 M.f. C4H6O2S4 Form Tech. is a yellow oil,
with an objectionable odour. V.p. 4 105 mPa (21C) S.g./density 1.394 (20C, tech.)
Solubility Miscible with acetone, benzene, ethanol, hexane.
COMMERCIALISATION:
History Herbicide introduced by Vondelingenplaat N.V.
APPLICATIONS:
ModeofactionContact herbicide, plant growth regulator and desiccant. Uses At 9 kg/
ha pre-em. on drilled crops, controlling seeding dicotolydonous weeds; at 28 gk/ha as
a pre-harvest desiccant of onions and peas; and to control the growth and splitting of
carrots. Formulation types EC.
dimexano 201
PRODUCTS:
Discontinued products TriPE* (Vondelingenplaat).
ANALYSIS:
Product analysis is by colorimetry (D. G. Clarke et al., Anal. Chem., 1951, 23, 1842) after
reduction.
Oral Acute oral LD50 for rats 340 mg tech./kg. Toxicity Class WHO (a.i.) O
ENVIRONMENTAL FATE:
Soil/Environment It does not persist in soil.
dimidazon
Herbicide
NOMENCLATURE:
Common name dimidazon (BSI, E-ISO); dimethazone* (withdrawn BSI name);
dimidazone ((m) F-ISO)
IUPACname 4,5-dimethoxy-2-phenylpyridazin-3(2H)-one
Chemical Abstracts name 4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone
CASRN[3295781] DevelopmentcodesBAS 255H (BASF)
SmilescodeCOc1cnn(c2ccccc2)c(=O)c1OC
COMMERCIALISATION:
History Herbicide introduced by BASF AG.
dinex; dinex-diclexine
NOMENCLATURE:
Common name dinex (BSI, E-ISO, (m) F-ISO); DN (JMAF); p(dinex) ((m) France)
IUPACname 2-cyclohexyl-4,6-dinitrophenol (I)
Chemical Abstracts name (I) Other names DNOCHP (dinex) CASRN[131895]
dinex; [317839] dinex-diclexine ECno2050425 DevelopmentcodesDN1 (dinex);
DN111 (dinex-diclexine)
PHYSICAL CHEMISTRY: Mol. wt. 266.3; (dinex-diclexine 447.6) M.f. C12H14N2O5;
(dinex-diclexine C24H37N3O5)
202 dinex; dinex-diclexine

COMMERCIALISATION:
History Dinex was introduced as an acaricide and insecticide by Dow Chemical Co., Ltd
(later DowElanco), and its dicyclohexylammonium salt (dinex-diclexine) by Fisons Ltd
(later Schering Agriculture).
PRODUCTS:
Discontinued products DynoneII* (FBC).
ADI/RfD (EPA) 0.002 mg/kg b.w. [1987], based on other dinitrophenols.
Toxicity Class WHO (a.i.) O ECClassification T; R23/24/25| N; R50, R53 (dinex and
dinex salts and esters)
dinocton
NOMENCLATURE:
Common name dinocton (BSI, E-ISO, (m) F-ISO, for a reaction product comprising
isomeric dinitro(octyl)phenyl methyl carbonates)
IUPACname for main components: (i) 2,4-dinitro-6-(1-propylpentyl)phenyl methyl
carbonate (I); (ii) 2-(1-ethylhexyl)-4,6-dinitrophenyl methyl carbonate (II); (iii) 2,6-dinitro-4-
(1-propylpentyl)phenyl methyl carbonate (III); (iv) 4-(1-ethylhexyl)-2,6-dinitrophenyl methyl
carbonate (IV)
Chemical Abstracts name (I), (II), (III), (IV) Other names dinocton-6 (i) +(ii);
dinocton-4 (iii) +(iv) CASRN[32534966] (i) +(ii); [19000589] (i); [19000523] (ii);
[32535083] (iii) +(iv); [6465516] (iii); [6465607] (iv)
DevelopmentcodesMC 1945 (i) +(ii); MC 1947 (iii) +(iv); TD 8537 (iii) +(iv)
COMMERCIALISATION:
History Acaricide and fungicide reported by M. Pianka (Proc. Crop Prot. Symp., 2nd.,
Magdeburg, 1966). Evaluated by Murphy Chemical Co. (later DowElanco).
Toxicity Class WHO (a.i.) O ECClassification Xn; R22| N; R50, R53
dinofenate
Herbicide
NOMENCLATURE:
Common name dinofenate (BSI)
IUPACname 2-sec-butyl-4,6-dinitrophenyl 2,4-dinitrophenyl carbonate
dinofenate 203
Chemical Abstracts name 2,4-dinitrophenyl 2-(1-methylpropyl)-4,6-dinitrophenyl

carbonate CASRN[61614628] SmilescodeCCC(C)c1cc(cc([N+](=O)[O-])
c1OC(=O)Oc2ccc(cc2[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide evaluated by Pennwalt.
dinopenton
NOMENCLATURE:
Common name dinopenton (BSI, E-ISO, (m) F-ISO)
IUPACname isopropyl 2-(1-methylbutyl)-4,6-dinitrophenyl carbonate
Chemical Abstracts name 2-(1-methylbutyl)-4,6-dinitrophenyl 1-methylethyl carbonate
CASRN[5386572]
SmilescodeCCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)OC(C)C)[N+](=O)[O-]
COMMERCIALISATION:
History Acaricide reported at 5th Int. Pestic. Congr., London, 1963 (M. Pianka, J. Sci. Food
Agric., 1966, 17, 47). Evaluated by Murphy Chemical Ltd (later DowElanco).
dinoprop
Herbicide
NOMENCLATURE:
Common name dinoprop (BSI, E-ISO, (m) F-ISO)
IUPACname 4,6-dinitro-o-cymen-3-ol
Chemical Abstracts name 3-methyl-2-(1-methylethyl)-4,6-dinitrophenol
Other names DNOIPP CASRN[7257412] SmilescodeCC(C)c1c(C)c(cc([N+]
(=O)[O-])c1O)[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide and insecticide.
204 dinoprop
dinosam
Herbicide
NOMENCLATURE:
Common name dinosame ((m) F-ISO); dinosam (BSI, E-ISO)
IUPACname 2-(1-methylbutyl)-4,6-dinitrophenol (I)
Chemical Abstracts name (I) Other names DNAP; DINOSAP CASRN[409736
3] SmilescodeCCCC(C)c1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide reported by A. S. Crafts (Plant Physiol., 1946, 21, 345). Introduced by
Standard Agricultural Chemicals Inc.
PRODUCTS:
Discontinued products Sinox General* (Standard).
ECClassification T; R23/24/25| N; R50, R53 (dinosam or its salts and esters)
dinoseb
OH CH3
O2N CHCH2CH3
NO2
HRACM WSSA 24; dinitrophenol
NOMENCLATURE:
Common name dinoseb (BSI, E-ISO, ANSI, WSSA); dinos(be) ((m) F-ISO); DNBP (JMAF)
IUPACname 2-sec-butyl-4,6-dinitrophenol
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenol CASRN[88
857] ECno2018617 DevelopmentcodesDN 289 (Dow); Hoe 26 150
SmilescodeCCC(C)c1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Composition Tech. is 9598%. Mol. wt. 240.2 M.f. C10H12N2O5 Form Orange solid;
(tech., orange-brown solid). M.p.3842C; (tech.: 3040C) V.p. 0.13 mPa (room
temperature) (Adv. Chem. Series, ACS, cited in ARS PPD) Kow logP = 2.29 (unstated pH)
(Agchem. Desk Ref.) Henry 6.0 104 Pa m3 mol1 (20C, calc.) S.g./density 1.265 (45C)
Solubility In water 52 mg/l (20C). Soluble in most organic solvents and in petroleum
oils. In ethanol 480, heptane 270 (both in g/kg). pKa 4.62 F.p. 177C
dinoseb 205
COMMERCIALISATION:
History Herbicidal activity reported by A. S. Crafts (Science, 1945, 101, 417). Introduced by
Dow Chemical Co. (later DowElanco). Patents US 2192197 (to Dow); DE 1088757; GB
909732 (both to Hoechst)
APPLICATIONS:
Biochemistry Inhibits respiratory electron transport, and uncouples oxidative
phosphorylation. ModeofactionSelective non-systemic herbicide with contact action.
Uses Dinoseb was used as the ammonium or an amine salt or acetate ester for post-
emergence weed control in cereals, undersown cereals, seedling alfalfa and peas at 2.5
kg/ha. Solutions of dinoseb in oil were used for pre-emergence control of annual weeds in
beans, peas and potatoes, for pre-harvest desiccation of hops, leguminous seed crops and
potatoes and for control of runners and suckers in raspberries and strawberries. Dinoseb
acetate was also used in combination with monolinuron pre-emergence in dwarf beans and
potatoes. Phytotoxicity Phytotoxic to cruciferous crops. Formulation types SL; EC; EO.
PRODUCTS:
Discontinued products Aretit* (Hoechst); Fanicide* (La Littorale); Farmon Desicoil
25* (Farm Protection); General Weedkiller* (Vertac); Ivosit* (Hoechst); Persevtox* (La
Quinoline); Premerge* (olamine and 2-hydroxypropylammonium salts) (Siapa, Tifa,Vertac);
Premerge 3* (olamine and diolamine salts) (Siapa, Tifa,Vertac); Selective Weedkiller*
(ammonium salt) (Vertac); Supersevtox* (diolamine and trolamine salts) (Schering).
ANALYSIS:
Product analysis by titration of a deriviative (CIPACHandbook, 1994, F, 327) or by
colorimetry of solutions in alkali (D. S. Farrington et al., Analyst (London), 1983, 108, 353).
Residues determined by glc of a derivative (Anal. Methods Pestic. Plant Growth Regul., 1972, 6,
639). See also Pestic. Anal. Man., I, 208.
ICSC.149 (1994). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 90/533/EEC.
Oral Acute oral LD50 for rats 58, guinea pigs 25 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits 80200, guinea pigs 500 mg/kg. Mild skin and eye irritant (rabbits).
NOEL In 6 mo feeding trials, rats receiving 100 mg/kg diet showed no ill-effects.
ADI/RfD (EPA) cRfD 0.001 mg/kg b.w. [1989]. Water GV Excluded from GV derivation
(U). Other Very toxic to man (uncouples oxidative phosphorylation).
Toxicity Class WHO (a.i.) Ib ECClassification R44| T; R24/25| R61| R62| Xi; R36| N;
R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens 26 mg/kg. Dietary LC50 (5 d) for Japanese quail 409,
ring-necked pheasant 515 mg/kg diet. Fish Highly toxic to fish. Bees Toxic to bees.
206 dinoseb
ENVIRONMENTAL FATE:
Animals In mammals, undergoes oxidation of the sec-butyl side-chain, conjugation, and in
rats (but not in mice) reduction of either of the nitro groups and acetylation of the amino
group formed. Soil/Environment Under normal conditions of use, persistence in soil
isc.26 weeks.
dinoseb acetate
Herbicide
NOMENCLATURE:
Common name dinoseb acetate (BSI, ISO-E, ANSI, WSSA); dinos(b ac) ((m) F-ISO);
DNBPA (JMAF)
IUPACname 2-sec-butyl-4,6-dinitrophenyl acetate
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenyl acetate
CASRN[2813958] DevelopmentcodesHoe 02904
SmilescodeCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Composition Tech. isc.94%. Mol. wt. 282.2 M.f. C12H14N2O6 Form Brown oil with an
aromatic vinegar-like odour; (tech. is a viscous brown oil). M.p.2627C B.p. 170C
/4 mmHg V.p. 28 mPa (43C); 183 mPa (60C) Solubility In water 2.2 g/l (20C).
Readily soluble in aromatic solvents. Stability Hydrolysed by acids and alkalis, and slowly
hydrolysed in neutral media.
COMMERCIALISATION:
History Herbicidal activity reported by H. Hrtel (Meded. Landbouwhogesch. Opzoekingsstn.
Staat Gent, 1960, 25, 1422). Introduced by Hoechst AG (later AgrEvo GmbH).
APPLICATIONS:
Biochemistry Inhibits respiratory electron transport, and uncouples oxidative
phosphorylation. ModeofactionSelective non-systemic herbicide with contact action.
Uses See dinoseb. Formulation types EC; WP. Compatibility Incompatible with
alkaline materials.
PRODUCTS:
Discontinued products Ivocit* (Hoechst); Phenotan* (Rhne-Poulenc).
ANALYSIS:
Product by spectrophotometry (D. S. Farrington et al., Analyst (London) 1983, 108 1284,
353360; CIPACHandbook, 1970, 1, 337341). By coulometry (B. G. Kratochvil & I. M. Al-
Daher Analyst (London) 1981, 106(1264), 796799). Residues by GLC of a derivative with
ECD (Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 639), or by spectrophotometry (ibid.
1967, 5, 390).
dinoseb acetate 207


ICSC.882 (1997). EU Status (1107/2009) See dinoseb.
Oral Acute oral LD50 for rats 6065 mg/kg. Inhalation LC50 (4 h) for rats 1.3 mg/l air.
NOEL (2 y) for rats 100 mg/kg diet, for dogs 8 mg/kg diet. Other Very toxic to man
(uncouples oxidative phosphorylation). Toxicity Class WHO (a.i.) Ib
ECClassification R44| R61| R62| T; R24/25| Xi; R36| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fish. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Rapidly degraded to dinoseb (q.v.).
dinosulfon
NOMENCLATURE:
Common name dinosulfon (BSI, E-ISO, (m) F-ISO)
IUPACname S-methyl O-2-(1-methylheptyl)-4,6-dinitrophenyl thiocarbonate
Chemical Abstracts name S-methyl O-[2-(1-methylheptyl)-4,6-
dinitrophenyl] carbonothioate CASRN[5386776] unstated stereochemistry
DevelopmentcodesMC 1143
SmilescodeCCCCCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)SC)[N+](=O)[O-]
COMMERCIALISATION:
History Acaricide and fungicide reported by M. Pianka & J. D. Edwards (J. Sci. Food
Agric., 1968, 19, 60) and M. Pianka & P. J. J. Sweet (ibid., pp. 672, 676). Evaluated by Murphy
Chemical Co. (later DowElanco).
dinoterb
Herbicide
OH
O2N C(CH3)3
NO2
HRACM WSSA 24; dinitrophenol
NOMENCLATURE:
Common name dinoterbe ((m) F-ISO); dinoterb (BSI, E-ISO)
208 dinoterb
IUPACname 2-tert-butyl-4,6-dinitrophenol
Chemical Abstracts name 2-(1,1-dimethylethyl)-4,6-dinitrophenol
Other names DNTBP CASRN[1420071] ECno2158138
DevelopmentcodesLS63 133 (Rhne-Poulenc) SmilescodeCC(C)(C)c1cc(cc([N+]
(=O)[O-])c1O)[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 240.2 M.f. C10H12N2O5 Form Pale yellow solid,
with a phenol-like odour. M.p.125.5126.5C V.p. 20 mPa (20C) Henry 1.07 Pa m3
mol1 (calc.) Solubility In water 4.5 mg/l (pH 5, 20C). In cyclohexanone, ethyl acetate,
DMSOc.200 g/kg. In alcohols, glycols, aliphatic hydrocarbonsc.100 g/kg. Soluble in aqueous
alkalis with the formation of salts. Stability Stable below the melting point. Decomposes
above 220C. Stable at least 34 d at pH 59 (22C).
COMMERCIALISATION:
History Herbicide reported by G. A. Emery etal. (Proc. Conf. EWRC/COLUMA, 2nd,
1965, p. 41) (for acetate) and by P. Poignant & P. Crisinel (C. R. Journ. Etud. Herbic. Conf.
COLUMA, 4th, 1967, p. 196). Introduced by Ppro (now Bayer AG) and by Murphy
Chemical Ltd (who no longer manufacture or market it). Patents FR 1475686; FR
1532332; GB 1126658; US 3565601 (all to Ppro) Manufacturers Bayer CropScience
APPLICATIONS:
Biochemistry Oxidative phosphorylation uncoupler, leading to membrane disruption.
ModeofactionSelective non-systemic herbicide with contact action. Uses Control of
annual broad-leaved weeds post-emergence in cereals, maize, alfalfa, and beet; and pre-
emergence in peas and beans. Also used for destruction of potato haulms.
Formulation types EC; SL .
ANALYSIS:
Product analysis by methylation with diazomethane followed by glc (CIPACHandbook, 1983,
1B, 1797). Residues by glc; details available from Bayer CropScience.
EU Rev. Rep. 8083/VI/97 (1997). EU Status (1107/2009) Not approved, 98/269/EC.
Oral Acute oral LD50 for rats 62, mice 25, rabbits 28 mg/kg. Skin and eye Acute
percutaneous LD50 for guinea pigs 150 mg/kg. NOEL (2 y) for rats 0.375 mg/kg diet.
ADI/RfD (ECCO) No ADI [1997]. Toxicity Class WHO (a.i.) Ib. ECClassification
R61| T+; R28| T; R24| R44| N; R50, R53: (salts and esters are R61| T+; R28| T; R24| N; R50,
R53)
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout 0.0034 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 98% is excreted in the faeces and urine
within 7 days.
dinoterb 209
dinoterbon
NOMENCLATURE:
Common name dinoterbon (BSI, E-ISO, (m) F-ISO)
IUPACname 2-tert-butyl-4,6-dinitrophenyl ethyl carbonate
Chemical Abstracts name 2-(1,1-dimethylethyl)-4,6-dinitrophenyl ethyl carbonate
CASRN[6073729]
SmilescodeCCOC(=O)Oc1c(cc(cc1C(C)(C)C)[N+](=O)[O-])[N+](=O)[O-]
COMMERCIALISATION:
History Acaricide and fungicide reported at 5th Int. Pestic. Congr., London, 1963 (M.
Pianka, J. Sci. Food Agric., 1966, 17, 47). Evaluated by Murphy Chemical Co. (later DowElanco).
diofenolan
Insecticide
O
O
CH2
O O CH2CH3
NOMENCLATURE:
Common name diof(nolane) ((m) F-ISO); diofenolan (BSI, E-ISO)
IUPACname A mixture of: (2RS,4SR)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl
ether (5080%) and (2RS,4RS)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl ether
(5020%)
Chemical Abstracts name A mixture of (2RS,4SR)-2-ethyl-4-[(4-phenoxyphenoxy)
methyl]-1,3-dioxolane and (2RS,4RS)-2-ethyl-4-[(4-phenoxyphenoxy)methyl]-
1,3-dioxolane CASRN[63837332] DevelopmentcodesCGA 059 205
SmilescodeCCC1OCC(COc2ccc(Oc3ccccc3)cc2)O1
PHYSICAL CHEMISTRY:
Composition A mixture of 5080% (2RS,4SR)- isomer with 5020% (2RS,4RS)- isomer.
Mol. wt. 300.3 M.f. C18H20O4 Form Clear, pale yellow viscous liquid. B.p. >250C
/101.325 kPa (OECD 103) V.p. 1.1 101 mPa (25C) (OECD 104) Kow logP = 4.8; 4.4
(cis- isomer); 4.3 (trans- isomer) (25C) (OECD 117) Henry 6.74 103 Pa m3 mol1
(calc.) S.g./density 1.141 (20C) Solubility In water 4.9 mg/l (25C) (OECD 105).
Miscible with methanol, acetone, toluene, hexane, n-octanol. Stability Hydrolytically stable
at pH 7. Rapidly degraded by light. pKa No dissociation in range pH 111
210 diofenolan
COMMERCIALISATION:
History Reported by H. P. Streibert etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1994, 1, 23).
Introduced by Ciba-Geigy AG (later Novartis Crop Protection AG).
APPLICATIONS:
ModeofactionInsect growth regulator with juvenile hormone activity. Inhibits
development of first and second instar larvae of scales. Uses Active against most scale
insects and eggs of some Lepidoptera in citrus, pome fruit, stone fruit, grapes, mango, olives,
nuts, tea and ornamentals. Formulation types EC.
PRODUCTS:
Discontinued products Arbor* (Novartis); Aware* (Ciba); Context* (Ciba).
ANALYSIS:
By hplc with uv detection.
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50
for rats (24 h) >2000 mg/kg. Not irritant to skin or eyes (rabbits). Not a skin sensitiser.
Inhalation LC50 (4 h) for rats >3100 mg/m3. NOEL (3 mo) for rats 12 mg/kg b.w.;
NOAEL (3 mo) for dogs 12 mg/kg b.w.. ADI/RfD 0.006 mg/kg (provisional).
ECOTOXICOLOGY:
Birds Acute oral LC50 for quail and ducks >2000 mg/kg. Fish LC50 (96 h) for bluegill
sunfish, catfish, carp and trout 1.01.7 mg/l. Daphnia LC50 (48 h) 0.5 mg/l. Algae LC50 (72
h) 0.072 mg/l. Bees LD50 (48 h, oral and contact) >96 mg/bee. Tech. material has a high
toxicity to the brood of the honeybee. Worms LC50 (14 d) 204 mg/kg soil.
ENVIRONMENTAL FATE:
Animals Intestinal absorption 80%. Rapid elimination. Tissue residues low.
Soil/Environment Rapid dissipation: field trials DT50c.6 d; laboratory DT50 <2 d. No
potential for mobility (RMF 0.15).
dioxabenzofos
Insecticide
S
O
P
OCH3
O
IRAC1B
NOMENCLATURE:
Common name dioxabenzofos (BSI, E-ISO, (m) F-ISO); salithion (JMAF)
dioxabenzofos 211
IUPACname (RS)-2-methoxy-4H-1,3,25-benzodioxaphosphinine 2-sulfide; (RS)-2-

methoxy-4H-1,3,25-benzodioxaphosphorine 2-sulfide
Chemical Abstracts name ()-2-methoxy-4H-1,3,2-benzodioxaphosphorin
2-sulfide CASRN[3811492] unstated stereochemistry ECno2232923
SmilescodeCOP1(=S)OCc2ccccc2O1
PHYSICAL CHEMISTRY: Mol. wt. 216.2 M.f. C8H9O3PS Form Tech. is a light yellow
powder. M.p.52.554C V.p. 420 mPa (20C) Henry 2.11 Pa m3 mol1 (calc.)
Solubility In water 43 mg/l (20C). In acetonitrile, cyclohexanone, xylene >1 (all in kg/kg,
2123C). Stability Stable in acidic to weakly alkaline media (pH 28).
COMMERCIALISATION:
History Insecticide reported by M. Eto & Y. Oshima (Agric. Biol. Chem., 1962, 26, 452).
Introduced by Sumitomo Chemical Co., Ltd. Patents JP 467645; JP 446747; GB 987378; FR
1360130
APPLICATIONS:
with contact, ingested and respiratory action. Uses Control of a wide range of boring,
chewing and sucking insects (Aphididae, Coccidae, Chilo spp., Curculionidae, Diaspididae,
Margarodidae, Lepidoptera, Plutella xylostella and Spodoptera spp.) in fruit, rice, tea,
tobacco and vegetables. Formulation types MG; EC; WP; GR; GP.
Compatibility Incompatible with strongly alkaline materials.
PRODUCTS:
Discontinued products Salithion* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc. Residues determined by glc with FPD (M. Eto & J. Miyamoto, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 431).
EHC 63 (1986) is a general review of organophosphorus insecticides.
Oral Acute oral LD50 for male rats 125, female rats 180, male mice 125 mg/kg.
Skin and eye Acute percutaneous LD50 for male rats 400, mice >1250 mg/kg.
Toxicity Class WHO (a.i.) II ECClassification T; R24/25, R39/25| N; R51, R53
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 7.8 mg/l.
212 dioxabenzofos
dioxacarb
Insecticide
O
C
CH3NH O O
O
IRAC1A
NOMENCLATURE:
Common name dioxacarb (BSI, E-ISO, ANSI, ESA, JMAF); dioxacarbe ((m) F-ISO)
IUPACname 2-(1,3-dioxolan-2-yl)phenyl methylcarbamate
Chemical Abstracts name 2-(1,3-dioxolan-2-yl)phenyl methylcarbamate
CASRN[6988212] ECno2302534 DevelopmentcodesC 8353
SmilescodeCNC(=O)Oc1ccccc1C2OCCO2
M.p.114115C V.p. 0.04 mPa (20C) Henry 1.49 106 Pa m3 mol1 (calc.)
S.g./density 1.46 (20C) Solubility In water 6 g/l (20C). In acetone 280,
cyclohexanone 235, DMF 550, dichloromethane 345, ethanol 80, xylene 9, hexane 0.18 (all
in g/l, 20C). Stability Relatively stable in neutral media, but decomposed in acidic and
alkaline media; DT50 (calc., 20C) 85 h (pH 5), 24.6 d (pH 7), 15 h (pH 9).
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., Suppl., 1968,
p. 39). Introduced by Ciba AG (later Ciba-Geigy AG). Patents BE 670630; GB 1122633
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide with contact and
stomach action. Gives rapid knockdown. Uses Control of cockroaches (including those
resistant to organochlorine and organophosphorus insecticides), flies, Bed bugs, and other
public health pests in household use, animal houses, industrial areas, and stored products.
Control of chewing and sucking foliar insect pests on a range of crops. Particular uses
included control of colorado beetle on potatoes, leafhoppers and planthoppers on rice,
capsid bugs on cocoa, and various Beetles on oilseed rape. Formulation types WP; EC.
PRODUCTS:
Discontinued products Dimox* (Chimitox); Elocron* (Ciba-Geigy); Famid* (Ciba-
Geigy).
ANALYSIS:
Product analysis by acidimetric titration (A. Becker & W. Zeizler, Fresenius Z. Anal. Chem.,
1971, 257, 125). Residues determined by glc with ECD of a derivative.
dioxacarb 213

EHC 64 (1986; a review of carbamate pesticides in general). EU Status (1107/2009) Not
ratsc.3000, rabbits 1950 mg/kg. Inhalation LC50 for ratsc.0.16 mg/l air. NOEL (90 d) for
rats 10 mg/kg daily; for dogs 2 mg/kg daily (marginal). Toxicity Class WHO (a.i.) II EPA
(formulation) II ECClassification T; R25| N; R51, R53
ECOTOXICOLOGY:
Birds Slightly toxic to birds. Fish LC50 (96 h) for rainbow trout 29, carp 32 mg/l.
Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, dioxacarb is rapidly absorbed and
oxidised to the N-methylol and hydrolysed to the corresponding phenol. Both breakdown
products are eliminated as conjugates (e.g. glycosides), 8590% elimination occurring
within 24 h. Plants In plants, persists on foliage for c.57 d. Soil/Environment
Dioxacarb is rapidly decomposed in soil. Persists on wall surfaces for up to 6 months.
dioxathion
IRAC1B
NOMENCLATURE:
Common name dioxane phosphate (JMAF); delnav * (former exceptions: Turkey, USSR);
dioxathion (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname S,S-(1,4-dioxane-2,3-diyl) O,O,O,O-tetraethyl bis(phosphorodithioate)
Chemical Abstracts name S,S-1,4-dioxane-2,3-diyl bis(O,O-diethyl phosphorodithioate)
CASRN[78342] ECno2011077 DevelopmentcodesHercules AC258
SmilescodeCCOP(=S)(OCC)SC1OCCOC1SP(=S)(OCC)OCC
PHYSICAL CHEMISTRY:
Composition Tech. is 6875%: 24% cis- , 48% trans- isomers,c.30% related compounds.
Mol. wt. 456.5 M.f. C12H26O6P2S4 Form Tech. is a brown liquid. S.g./density 1.257
(26C) Solubility Insoluble in water. In hexane, kerosene 10 g/kg; soluble in most organic
solvents. Stability Stable in water at neutral pH, but hydrolysed by alkali or on heating.
Unstable to iron or tin surfaces or when mixed with certain carriers.
COMMERCIALISATION:
History Insecticide reported by W. R. Diveley etal. (J. Am. Chem. Soc., 1959, 81, 139). The
cis- is more toxic than the trans- isomer to flies and rats (B. W. Arthur & J. E. Casida, J.
214 dioxathion
Econ. Entomol., 1959, 52, 20). Introduced by Hercules Inc. (later by Nor-Am Chemical Co.).
Patents US 2725328; US 2815350
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact insecticide and
acaricide. Uses For treatment of livestock to control ectoparasites, including ticks and
biting flies. It was also used for residual control of chigoes, fleas, mites and ticks in parks
and recreation areas. Formulation types EC.
PRODUCTS:
Discontinued products Delnav* (NOR-AM); Deltic* (NOR-AM).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by glc (D. C. Abbott et al., Pestic.
Sci., 1970, 1, 10). See also Pestic. Anal. Man., II, 186.2450.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. 11 (1968),
19 (1972). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Oral Acute oral LD50 for male albino rats 43, female rats 23 mg/kg.
Skin and eye Acute percutaneous LD50 for male albino rats 235, female albino rats
63 mg/kg. NOEL Cholinesterase inhibition was observed in female rats receiving 10
mg/kg diet. ADI/RfD (JMPR) 0.0015 mg/kg b.w. [1968]. Toxicity Class WHO (a.i.) Ib
ECClassification T+; R26/28| T; R24| N; R50, R53| concn. dep.
diphenyl sulfone
Acaricide
NOMENCLATURE:
Common name diph(nylsulfone) (F-ISO, accepted in lieu of a common name.); diphenyl
sulfone (BSI, E-ISO)
IUPACname diphenyl sulfone
Chemical Abstracts name 1,1-sulfonylbis[benzene] Other names DPS
CASRN[127639] SmilescodeO=S(=O)(c1ccccc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 218.3 M.f. C12H10O2S
COMMERCIALISATION:
History Acaricide reported by J. K. Eaton & R. G. Davies (Ann. Appl. Biol., 1950, 37, 471).
diphenyl sulfone 215

dipropetryn
Herbicide
CH3CH2S N NHCH(CH3)2
N N
NHCH(CH3)2
NOMENCLATURE:
Common name dipropetryn (BSI, E-ISO, ANSI, WSSA); diprop(tryne) ((f) F-ISO)
IUPACname 6-ethylthio-N2,N4-diisopropyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-(ethylthio)-N,N-bis(1-methylethyl)-1,3,5-
triazine-2,4-diamine CASRN[4147517] DevelopmentcodesGS 16 068
SmilescodeCCSc1nc(NC(C)C)nc(NC(C)C)n1
PHYSICAL CHEMISTRY: Mol. wt. 255.4 M.f. C11H21N5S Form Colourless powder.
M.p.104106C V.p. 0.097 mPa (20C) Kow logP = 3.810 Henry 1.55 103 Pa m3 mol1
dichloromethane 300, toluene 220, methanol 190, n-octanol 130, hexane 9 (all in g/l, 20C).
Stability Stable in neutral and alkaline media, but hydrolysed in strongly acidic media; DT50
2428 d (pH 1, 25C), >2.5 y (7<pH<13). Decomposed by uv light.
COMMERCIALISATION:
History Herbicide reported by G. A. Buchanan & D. L. Thurlow (Ala. Agr. Exp. Sta.
Highlights, 1968, 15(2), 7). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
Patents CH 337019; GB 814948
APPLICATIONS:
site. ModeofactionSelective systemic herbicide, absorbed by the roots and foliage, with
rapid translocation acropetally through the xylem, accumulating in the apical meristems
and leaf tips. Uses Pre-emergence control of annual broad-leaved weeds and grasses in
cotton and water melons at 1.253.5 kg/ha. Formulation types FW; SC. WP.
PRODUCTS:
Discontinued products Cotofor* (Ciba-Geigy); Sancap* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc or by titration with perchloric acid in acetic acid. Residues
determined by glc with FPD (B. G. Tweedy & R. A. Kahrs, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 493; K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
LD50 for rabbits >10000 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). No skin
216 dipropetryn
sensitisation (guinea pigs). NOEL (98 d) for rats 400 mg/kg diet (27 mg/kg daily); (133 d)
for dogs 400 mg/kg diet (13 mg/kg daily). Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Practically non-toxic to birds. Fish LC50 (96 h) for rainbow trout 2.7, bluegill sunfish
1.6 mg/l. Bees Practically non-toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Degradation involves dealkylation of the side-chains, splitting of the
ring, and evolution of CO2. Soil DT50c.100 d.
dipyrithione
Fungicide
O
N S S
N
O
NOMENCLATURE:
Common name dipyrithione (BSI, E-ISO, (f) F-ISO, RINN)
IUPACname di-2-pyridyl disulfide 1,1-dioxide
Chemical Abstracts name 2,2-dithiobis[pyridine] 1,1-dioxide CASRN[3696284]
DevelopmentcodesOSY-20 SmilescodeO=n1ccccc1SSc2ccccn2=O
COMMERCIALISATION:
History Fungicide and bactericide discovered by Olin Chemicals and developed by
Yashima Chemical Industry Co. Ltd and Sankyo Co., Ltd.
APPLICATIONS: Uses Developed as a fungicide for use in rice.
PRODUCTS:
Discontinued products Omadine* (Yashima); Omadine disulfide* (Yashima); Omadine
DS* (Yashima).
disul; disul-sodium
Herbicide
NOMENCLATURE:
Common name sesone (WSSA); disul (E-ISO, (m) F-ISO); 2,4-DES (BSI, Australia, USSR)
IUPACname 2-(2,4-dichlorophenoxy)ethyl hydrogen sulfate (I)
disul; disul-sodium 217

Chemical Abstracts name (I) Other names SES CASRN[149268] disul; [136
787] disul-sodium ECno2052595 disul
PHYSICAL CHEMISTRY: Mol. wt. 287.1; (sodium salt 309.1) M.f. C8H8Cl2O5S;
(sodium salt C8H7Cl2NaO5S) Form The sodium salt forms colourless crystals.
M.p.170C (sodium salt) V.p. Negligible (sodium salt, room temperature)
Solubility In water 250 g/kg (sodium salt). Insoluble in most organic solvents except
methanol. The calcium salt is sufficiently soluble to avoid precipitation from solutions
of 2,4-DES in hard water. Stability 2,4-DES-sodium is hydrolysed by alkali to form
2-(2,4-dichlorophenoxy)ethanol and sodium sulfate.
COMMERCIALISATION:
History Herbicide reported by L. J. King etal. (Contrib. Boyce Thompson Inst., 1950, 16,
191). Introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.). Patents US 2573769
APPLICATIONS:
Biochemistry 2,4-DES-sodium is not itself phytotoxic, but is converted in moist soil
to 2-(2,4-dichlorophenoxy)ethanol which is oxidised to 2,4-D. Uses It was used as a
mixture with simazine to control annual weeds pre-em. in maize, soft fruits, roses, certain
established perennial crops and certain ornamental trees and shrubs.
PRODUCTS:
Discontinued products Crag Herbicide I* (disul) (Rhne-Poulenc); Crag
Sesone* (disul) (Rhne-Poulenc); Herbon* (sodium salt) (Atlas Interlates);
Discontinuedmixtures Herbon Blue* (+simazine) (Atlas).
ANALYSIS:
ANALYSIS: is by colorimetry of a derivative (J. N. Hogsett & G. L. Funk, Anal. Chem., 1954,
26, 849).
ICSC.142 (disul-sodium; 1995).
Oral Acute oral LD50 for rats 730 mg/kg. NOEL In 2 y trials, rats receiving 2000 mg/kg
diet suffered no ill-effect. Toxicity Class WHO (a.i.) III ECClassification Xn; R22| Xi;
R38, R41 (disul)
ditalimfos
Fungicide
NOMENCLATURE:
Common name ditalimphos ((m) F-ISO); ditalimfos (BSI, E-ISO, ANSI)
IUPACname O,O-diethyl phthalimidophosphonothioate;
N-diethoxyphosphinothioylphthalimide
218 ditalimfos
Chemical Abstracts name O,O-diethyl (1,3-dihydro-1,3-dioxo-2H-

isoindol-2-yl)phosphonothioate CASRN[5131248] ECno2258758
DevelopmentcodesDowco 199 SmilescodeCCOP(=S)(OCC)N1C(=O)
c2ccccc2C1=O
PHYSICAL CHEMISTRY: Mol. wt. 299.3 M.f. C12H14NO4PS Form Colourless plates
with a mild thiophosphate odour. M.p.8384C V.p. 1.93 101 mPa (25C)
Solubility In water c.133 mg/l (room temperature). Soluble in hexane, cyclohexane,
ethanol; very soluble in benzene, carbon tetrachloride, ethyl acetate and xylene.
Stability Stable to uv light; its stability is reduced at pH >8 or above its m.p. No
indication during storage of thiono-thiolo isomerisation which is characteristic of some
phosphorothioate esters.
COMMERCIALISATION:
History Fungicide reported by H. Tolkmith (Nature (London), 1966, 211, 522). Introduced
by Dow Chemical Co. (later DowElanco). Patents BE 661891, GB 1034493.
APPLICATIONS:
ModeofactionNon-systemic foliar fungicide with protectant and curative activity.
Uses For control of powdery mildew on ornamentals (primarily roses) and vegetables
(cucurbits) under glass, as well as under field conditions, at 3050 g/100 l; on apples, at
255- g/100 l; and cereals,at 500550 g/ha. Also used against Venturia inaequalis on apples
at 37.5100 g/100 l. Phytotoxicity Liable to russet certain apple cultivars, particularly
Golden Delicious.
Compatibility Not compatible with alkaline materials.
PRODUCTS:
Discontinued products Plondrel* (DowElanco).
ANALYSIS:
Product analysis is by uv spectroscopy. Residues by glc.
Oral Acute oral LD50 for rats 49305660, male guinea pigs 5660 mg/kg.
Skin and eye Skin irritant; allergenic. Toxicity Class WHO (a.i.) U
ECClassification Xi; R38| R43
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens 4500 mg/kg.
ditalimfos 219
dithicrofos
Insecticide
IRAC1B
NOMENCLATURE:
Common name dithicrofos (BSI, E-ISO, (m) F-ISO)
IUPACname S-(6-chloro-3,4-dihydro-2H-1-benzothi-in-4-yl) O,O-diethyl
phosphorodithioate
Chemical Abstracts name S-(6-chloro-3,4-dihydro-2H-1-benzothiopyran-4-yl)
O,O-diethyl phosphorodithioate CASRN[41219312] unstated stereochemistry
DevelopmentcodesHoe 19 510 SmilescodeCCOP(=S)(OCC)SC1CCSc2ccc(Cl)
cc12
PHYSICAL CHEMISTRY: Mol. wt. 368.9 M.f. C13H18ClO2PS3
COMMERCIALISATION:
History Insecticide evaluated by Hoechst AG.
APPLICATIONS:
2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (I)
Chemical Abstracts name (I) CASRN[21709444] DevelopmentcodesC 13
963 SmilescodeCN(C)C(=O)Oc1ccccc1C2SCCS2
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., Suppl., 1968,
p. 39). Evaluated by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
220
2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate
DKA-24
Herbicide safener
CH2CH=CH2
O NH
HCCl2 C C O
N CH2
CH2=CHCH2
NOMENCLATURE:
IUPACname N1,N2-diallyl-N2-dichloroacetylglycinamide
Chemical Abstracts name 2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-2-
propenylacetamide CASRN[97454007] DevelopmentcodesDKA-24 (MV)
SmilescodeClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C
PHYSICAL CHEMISTRY: Mol. wt. 265.1 M.f. C10H14Cl2N2O2 Form Pale yellow liquid.
Kow logP = 1 Solubility In water 24.2 g/l (20C). In acetone, chloroform, DMF >200 g/l.
Stability Stable 140C, and between pH 4.5 and 8.3.
COMMERCIALISATION:
History Herbicide safener reported by J. Nagy & K. Balogh (Proc. Br. Crop Prot. Conf.
Weeds, 1985, 1, 107). Introduced by szakmagyarorszgi Vegyimvek Chemical Works,
North Hungary (later SagroChem Co., Ltd). Patents HU 2143821
APPLICATIONS: Uses A safener at 2001000 g/ha for thiocarbamate or
2-chloroacetanilide herbicides on maize. Formulation types EC.
Oral Acute oral LD50 for rats 25002520, male mice 1010, female mice 1660 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Non-irritating to eyes and
skin.
DMCP
Insecticide
Cl
O
O
P
S
O
NOMENCLATURE: S(4-chlorophenyl) O,O-dimethyl phosphorothioate
Common name DMCP (JMAF)

IUPACname S-(4-chlorophenyl) O,O-dimethyl phosphorothioate
S(4-chlorophenyl) O,O-dimethyl phosphorothioate
DMCP 221
CASRN[3309873] DevelopmentcodesB-3242
PHYSICAL CHEMISTRY: Mol. wt. 252.7 M.f. C8H10ClO3PS
COMMERCIALISATION:
History Insecticide marketed by Kumiai Chemical Industry Co. Ltd.
PRODUCTS:
Discontinued products Fujithion* (Kumiai).
DMPA
Herbicide
NOMENCLATURE:
Common name DMPA (WSSA)
IUPACname O-2,4-dichlorophenyl O-methyl isopropylphosphoramidothioate
Chemical Abstracts name O-(2,4-dichlorophenyl) O-methyl (1-methylethyl)
phosphoramidothioate CASRN[299854] DevelopmentcodesK 22 023; Dowco
118 SmilescodeCOP(=S)(NC(C)C)Oc1ccc(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 314.2 M.f. C10H14Cl2NO2PS
COMMERCIALISATION:
History Herbicide introduced by Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Zytron* (DowElanco).
dodicin
Fungicide
NOMENCLATURE:
Common name dodicin (BSI, E-ISO, (f) F-ISO, BAN)
IUPACname N-[2-(2-dodecylaminoethylamino)ethyl]glycine; 3,6,9-triazahenicosanoic
acid
Chemical Abstracts name N-[2-[[2-(dodecylamino)ethyl]amino]ethyl]glycine
CASRN[6843976] SmilescodeCCCCCCCCCCCCNCCNCCNCC(=O)O
COMMERCIALISATION:
History Fungicide and surface active agent.
222 dodicin
dofenapyn
Acaricide
NOMENCLATURE:
Common name dof(napyne) ((m) F-ISO); dofenapyn (BSI, E-ISO)
IUPACname 4-(pent-4-ynyloxy)phenyl phenyl ether
Chemical Abstracts name 1-(4-pentynyloxy)-4-phenoxybenzene
ASRN[42873803] DevelopmentcodesCGA 29 170
SmilescodeC#CCCCOc1ccc(Oc2ccccc2)cc1
COMMERCIALISATION:
History Acaricide discovered by Ciba-Geigy AG.
PRODUCTS:
Discontinued products Acaban* (Ciba).
drazoxolon
Fungicide
O
O
NH N
N
Cl CH3
NOMENCLATURE:
Common name drazoxolon (BSI, E-ISO, (m) F-ISO)
IUPACname 4-(2-chlorophenylhydrazono)-3-methyl-1,2-oxazol-5(4H)-one;
4-(2-chlorophenylhydrazono)-3-methylisoxazol-5(4H)-one
Chemical Abstracts name 3-methyl-4,5-isoxazoledione 4-[(2-chlorophenyl)
hydrazone] CASRN[5707697] ECno2271978 DevelopmentcodesPP781
SmilescodeCC1=NOC(=O)C1=NNc2ccccc2Cl
PHYSICAL CHEMISTRY: Mol. wt. 237.6 M.f. C10H8ClN3O2 Form Yellow crystals.
M.p.167C V.p. 0.53 mPa (30C) Kow logP = 2.6 Solubility In water <10 g/l (20C).In
ethanol 10, chloroform 100, ketones 50, aromatic hydrocarbons 40 (all in g/kg). Practically
insoluble in acids and aliphatic hydrocarbons. Stability Stable in storage under normal
conditions. Stable to acids; dissolves in aqueous alkalis to form stable, soluble salts.
COMMERCIALISATION:
History Fungicide reported by M. J. Geoghegan (Proc. Br. Insectic. Fungic. Conf., 4th, 1967, 1,
451). Introduced by ICI Plant Protection Division (later Zeneca Agrochemicals).
Patents GB 999097
drazoxolon 223
APPLICATIONS:
ModeofactionFoliar fungicide and seed treatment with protective and curative
action. Uses Control of powdery mildews on roses, blackcurrants, and other crops;
coffee rust; tea blister blight; Ganoderma spp. on rubber trees; etc. Also seed treatment
for control of Pythium and Fusarium spp. in peas, beans, peanuts, maize, cotton, and grass.
Phytotoxicity Mixtures with dodine are phytotoxic to apples. Formulation types SC.
FS . Compatibility Incompatible with lime sulfur.
PRODUCTS:
Discontinued products Ganocide* (ICI); Mil-Col* (Zeneca); SAIsan* (ICI).
ANALYSIS:
Product and residue analysis by colorimetry (S. H.Yuen, Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 665).
Oral Acute oral LD50 for rats 126, mice 129, rabbits 100120, guinea pigs 12.525, dogs 17,
cats 50100 mg/kg. Skin and eye Non-irritating to skin and eyes, but some sensitisation
may occur, and prolonged contact should be avoided. Inhalation Rats exposed to 0.004
mg/l air for 15 daily periods of 6 h showed no toxic effect. Causes some lung irritation;
avoid vapour concentrations >0.0005 mg/l air. NOEL In 90 d feeding trials, rats receiving
30 mg/kg diet showed no ill-effects. Toxicity Class WHO (a.i.) II ECClassification T;
R25| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for hensc.100 mg/kg. Fish LC50 (96 h) for brown trout 0.55 mg/l.
DSP
Insecticide
IRAC1B
NOMENCLATURE:
Common name DSP (JMAF)
IUPACname O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate;
4-diethoxyphosphinothioyloxy-N,N-dimethylbenzenesulfonamide
Chemical Abstracts name O-[4-[(dimethylamino)sulfonyl]phenyl] O,O-diethyl
phosphorothioate CASRN[3078975] DevelopmentcodesNK 0795
SmilescodeCCOP(=S)(OCC)Oc1ccc(cc1)S(=O)(=O)N(C)C
COMMERCIALISATION:
History Insecticide introduced by Nippon Soda Co., Ltd.
224 DSP
APPLICATIONS:
PRODUCTS:
Discontinued products Kayaace* (Nippon Soda).
EBP
Fungicide
IRAC1B
NOMENCLATURE:
Common name EBP (JMAF)
IUPACname S-benzyl O,O-diethyl phosphorothioate
Chemical Abstracts name O,O-diethyl S-(phenylmethyl) phosphorothioate
CASRN[13286323] SmilescodeCCOP(=O)(OCC)SCc1ccccc1
COMMERCIALISATION:
History Fungicide introduced by Kumiai Chemical Industry Co., Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Kitazin* (Kumiai).
eglinazine-ethyl; eglinazine
Herbicide
Cl N NHCH2CO2H
N N
CH3CH2NH
NOMENCLATURE:
Common name eglinazine (for acid) (BSI, E-ISO, (f) F-ISO, WSSA)
IUPACname N-(4-chloro-6-ethylamino-1,3,5-triazin-2-yl)glycine (for acid)
Chemical Abstracts name N-[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]glycine (for
acid) CASRN[6616804] ester; [68228193] acid DevelopmentcodesMG-06
(ester)
eglinazine-ethyl; eglinazine 225

PHYSICAL CHEMISTRY:
Composition Tech. isc.96%. Mol. wt. 259.7; (acid 231.6) M.f. C9H14ClN5O2 (ester);
C7H10ClN5O2 (acid) Form Colourless crystals (ester). M.p.228230C (ester)
V.p. 0.027 mPa (20C) (ester) Solubility In water 300 mg/l (25C) (ester). In acetone
200, hexane 20, xylene 40 (all in g/l, 25C) (ester). Stability Stable at room temperature
at pH 58. Hydrolysed on heating with acids or alkalis, forming the hydroxytriazine (which
is herbicidally inactive). Stable to light. Decomposes at 250C.
COMMERCIALISATION:
History The ethyl ester introduced as a herbicide by Nitrokmia Ipartelepek.
APPLICATIONS: Uses Eglinazine-ethyl was used pre-emergence for control of loose
silky-bent (Apera spica-venti) and scentless mayweed (Matricaria perforata) in cereals at
3 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products MG06* (Nitrokmia).
ANALYSIS:
Product analysis by glc. Residues determined by glc with TID.
Oral Acute oral LD50 for rats and mice >10000, guinea pigs >3375 mg/kg.
Skin and eye Acute percutaneous LD50 for rats and rabbits >10000 mg/kg. Non-irritating
to skin and eyes. Other Acute i.p. LD50 for rats and mice >7100 mg/kg. No evidence of
cumulative toxicity. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
EI 1642
Insecticide
NOMENCLATURE:
IUPACname S-methyl N-(carbamoyloxy)thioacetimidate
Chemical Abstracts name methyl N-[(aminocarbonyl)oxy]ethanimidothioate
CASRN[16960397] DevelopmentcodesEI 1642
SmilescodeCSC(=NOC(=O)N)C
PHYSICAL CHEMISTRY: Mol. wt. 148.2 M.f. C4H8N2O2S Form Colourless crystals.
M.p.103104C Solubility In water 45 g/kg (25C). In acetone 170, ethanol 100,
methanol 300, isopropanol 30 (all in g/kg, 25C); practically insoluble in kerosine, toluene.
COMMERCIALISATION:
History Insecticide evaluated by E. I. du Pont de Nemours & Co.
226 EI 1642
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Effective as a foliar spray (150300 mg/l)
against aphids, lepidopterous and many other insect pests. Formulation types WP.
Oral The oral lethal dose for male rats isc.60 mg/kg. Skin and eye Percutaneous lethal
dose for rabbits is >3400 mg/kg; it is not a skin irritant. NOEL In a 14 d trial with rats, ten
doses of 12 mg/kg showed no cumulative toxicity.
EL 177
Herbicide
NOMENCLATURE:
IUPACname 1-tert-butyl-5-cyano-N-methylpyrazole-4-carboxamide
Chemical Abstracts name 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-
4-carboxamide CASRN[98477077] DevelopmentcodesEL-177; LYI 81 977
SmilescodeCNC(=O)c1cnn(c1C#N)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 206.2 M.f. C10H14N4O Form Crystalline solid.
M.p.164166C Kow logP = 1.3 Solubility Readily soluble in acetone, DMSO.
Stability Stable to light; and to hydrolysis at pH 3 and pH 7, slowly hydrolysed at pH 11.
COMMERCIALISATION:
History Herbicide reported by H. E. Chamberlain etal. (Proc. 1987 Br. Crop Prot. Conf. -
Weeds, 1, 35). Introduced by Eli Lilly.
Oral Acute oral LD50 for mice and male rats >500 mg tech./kg, for female rats >50 mg/kg.
Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not a skin irritant; slight
eye irritant (rabbits). NOEL (42 d) for female rats 57 mg/kg daily, slight increase in liver
enzyme activity in males. Other Not teratogenic in rats at 250 mg/kg daily (highest dose
tested). Not mutagenic or genotoxic in Ames assay.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >500 mg/kg. Fish LC50 (96 h) for bluegill sunfish
>100 mg/l, rainbow trout >62 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Soil/water distribution coefficient 0.31 (coarse-), 0.4 (medium-) and
0.45 (fine-textured soil).
EL 177 227
EMPC
Insecticide
NOMENCLATURE:
Common name EMPC (JMAF)
IUPACname 4-ethylthiophenyl methylcarbamate
Chemical Abstracts name 4-(ethylthio)phenyl methylcarbamate CASRN[18809579]
DevelopmentcodesNK-1 SmilescodeCCSc1ccc(OC(=O)NC)cc1
COMMERCIALISATION:
History Insecticide introduced by Nippon Kayaku Co., Ltd. Registration in Japan cancelled
in 1974.
APPLICATIONS:
PRODUCTS:
Discontinued products Toxamate* (Nippon Kayaku).
endothion
IRAC1B
NOMENCLATURE:
Common name endothion (BSI, E-ISO, (m) F-ISO, ESA, ex ANSI)
IUPACname S-5-methoxy-4-oxo-4H-pyran-2-ylmethyl O,O-dimethyl phosphorothioate;
2-dimethoxyphosphinoylthiomethyl-5-methoxypyran-4-one
Chemical Abstracts name S-[(5-methoxy-4-oxo-4H-pyran-2-yl)methyl]
O,O-dimethyl phosphorothioate CASRN[2778043] ECno2204723
Developmentcodes7175 RP (Rhne-Poulenc); AC18 737 (Cyanamid); FMC 5767
(FMC) SmilescodeCOc1coc(CSP(=O)(OC)OC)cc1=O
COMMERCIALISATION:
History Insecticide reported by F. Chaboussou & P. Ramadier (Rev. Zool. Agric. Appl., 1957,
55, 116). Introduced by Rhne-Poulenc Phytosanitaire and later by American Cyanamid Co.
and FMC Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Endocide* (Rhne-Poulenc).
228 endothion
Toxicity Class WHO (a.i.) O ECClassification T; R24/25
endrin
Insecticide
NOMENCLATURE:
Common name nendrin (Republic of South Africa); endrine ((f) F-ISO); endrin (BSI,
E-ISO, ESA, JMAF)
IUPACname (1R,4S,4aS,5S,6S,7R,8R,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-
octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
Chemical Abstracts name (1a,2,2a,3,6,6a,7,7a)-3,4,5,6,9,9-hexachloro-
1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene CASRN[72208]
ECno2007757 DevelopmentcodesExperimental Insecticide 269 (Hyman)
SmilescodeClC1=C(Cl)C2(Cl)C3C4CC(C5OC54)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. is 92%. Mol. wt. 380.9 M.f. C12H8Cl6O Form Colourless crystalline
solid; (tech. is a light tan solid). M.p.226230C (decomp.); (tech >200C, decomp.) V.p.
2 105 mPa (20C) S.g./density 1.64 (20C) Solubility Negligible in water. Moderately
soluble in acetone, benzene; sparingly in alcohols, petroleum hydrocarbons. Stability Tech.
decomposes >200C.
COMMERCIALISATION:
History Developed by Shell International Chemical Co. after introduction by J. Hyman &
Co. Patents US 2676132
APPLICATIONS:
ModeofactionContact insecticide. Uses Endrin is a foliar insecticide which acts against
a wide range of pests particularly Lepidoptera. It was used at 0.20.5 kg/ha on cotton,
maize, sugar cane, upland rice and many other crops. Formulation types EC; GR; WP.
PRODUCTS:
Discontinued products Endrex* (Shell); Mendrin* (Shell); Nendrin* (Velsicol).
ANALYSIS:
Product analysis by i.r. spectroscopy (CIPACHandbook, 1983, 1B, 1805; FAO Specification
(CP/46); AOACMethods 18th Ed., 961.05; Organochlorine Insecticides 1973), by tlc
(AOACMethods 18th Ed., 972.05), or by potentiometric titration of liberated chloride ion
(CIPACHandbook, 1994, F, 190), or by glc; mixtures with DDT and with parathion-methyl by
i.r. spectroscopy (CIPACHandbook, 1983, 1B, 1760, 1819). Residues determined by glc, tlc
or paper chromatography (AOACMethods, 18th Ed., 970.52), or by glc with ECD (Analyst
(London), 1979, 104, 425; G. M. Telling et al., J. Chromatogr., 1977, 137, 405; M. A. Luke et al., J.
endrin 229
Assoc. Off. Anal. Chem., 1981, 64, 1187; A. Ambrus et al., ibid., p. 733; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 0393). In drinking water by glc with ECD (AOACMethods, 18th Ed.,
990.06). See also Pestic. Anal. Man., I, 204, 208, 301, 302, 303, 502.
EHC 130 (1992). JMPR Mtg. 65 (1992); JMPR Evaln. 25 (1975). HSG 60 (1991). PDS 1 (1975).
ICSC.023 (2000). IARC 5 (1974). EU Status (1107/2009) Considered to be outside the
scope of the Directive; already banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 3
Oral Acute oral LD50 for rats 7.517.5 mg/kg. Skin and eye Acute percutaneous LD50
for female rats 15 mg/kg. NOEL (2 y) for rats and dogs 1 mg/kg diet (0.025 mg/kg b.w.
for dogs); rats and mice showed no carcinogenic response. ADI/RfD (JMPR) 0.0002 mg/
kg b.w. (PTDI) [1994]; (EPA) cRfD 0.0003 mg/kg b.w. [1991]. Water GV 0.6 ;g/l Other
Produces neurotoxic effects. Toxicity Class WHO (a.i.) Ib ECClassification T+; R28| T;
R24| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for birds 0.755.64 mg/kg. Fish LC50 (24 h) for fish 0.755.6 mg/l.
ENVIRONMENTAL FATE:
Animals It is rapidly metabolised in animals to hydrophilic metabolites which are excreted
(M. R. Baldwin et al., Pestic. Sci., 1976, 7, 575). Continuous exposure to endrin in diets results
in only a limited accumulation in body fat.
enoxastrobin
Fungicide
CH3
O
N
O
Cl H3C CO2Me
NOMENCLATURE:
Common name enoxastrobin (pa ISO)
IUPACname methyl 2-{2-[({[3-(4-chlorophenyl)-1-methylprop-2-enylidene]amino}oxy)
methyl]phenyl}-3-methoxyacrylate
Chemical Abstracts name methyl 2-[[[[3-(4-chlorophenyl)-1-methyl-2-propen-1-
ylidene]amino]oxy]methyl]--(methoxymethylene)benzeneaceate
CASRN[238410112] DevelopmentcodesSYPZ071 SmilescodeC\C(/C=C/
C1=CC=C(Cl)C=C1)=N/OCC2=CC=CC=C2/C(C(OC)=O)=C\OC
230 enoxastrobin
EPBP
Insecticide
IRAC1B
NOMENCLATURE:
Common name EPBP (JMAF)
IUPACname O-2,4-dichlorophenyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-(2,4-dichlorophenyl) O-ethyl phenylphosphonothioate
CASRN[3792594] DevelopmentcodesS-7 (Nissan)
SmilescodeCCOP(=S)(Oc1ccc(Cl)cc1Cl)c2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. isc.90%. Mol. wt. 347.2 M.f. C14H13Cl2O2PS Form Light brown
oil. B.p. 206C /5 mmHg V.p. 5.09 105 mPa (200C) S.g./density 1.312 (24C)
Solubility Practically insoluble in water; soluble in most organic solvents.
COMMERCIALISATION:
History Insecticide introduced by Nissan Chemical Industries Ltd. Patents US 3318764
APPLICATIONS:
insecticide. Uses Used mainly to control soil-dwelling pests such as Agrotis fucosa,
Phyllotreta striolata, Rhizoglyphus echinopus and Hylemya spp. etc., using the dust at
1.83.0 kg/ha. Formulation types DP .
PRODUCTS:
Discontinued products S7* (Nissan); SSeven* (Nissan).
ANALYSIS:
Product analysis by glc. Residues determined by glc.
Oral Acute oral LD50 for mice 275 mg/kg. Toxicity Class WHO (a.i.) II
epofenonane
Insecticide
NOMENCLATURE:
Common name epofenonane (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname 6,7-epoxy-3-ethyl-7-methylnonyl 4-ethylphenyl ether
Chemical Abstracts name 2-ethyl-3-[3-ethyl-5-(4-ethylphenoxy)pentyl]-2-
methyloxirane CASRN[57342026] DevelopmentcodesRo 103108
SmilescodeCCC(CCOc1ccc(CC)cc1)CCC2OC2(C)CC
epofenonane 231
COMMERCIALISATION:
History Insect growth regulator evaluated by Hoffmann-La Roche & Co.
epronaz
Herbicide
NOMENCLATURE:
Common name epronaz (BSI, E-ISO, (m) F-ISO)
IUPACname N-ethyl-N-propyl-3-propylsulfonyl-1H-1,2,4-triazole-1-carboxamide
Chemical Abstracts name N-ethyl-N-propyl-3-(propylsulfonyl)-1H-1,2,4-triazole-
1-carboxamide CASRN[59026083] DevelopmentcodesBTS 30 843
SmilescodeCCCN(CC)C(=O)n1cnc(n1)S(=O)(=O)CCC
COMMERCIALISATION:
History Herbicide reported by L. G. Copping & R. F. Brookes (Proc. Br.Weed Control Conf.,
12th, 1974, 2, 809). Evaluated by Boots Co., Ltd (later Schering Agriculture).
erbon
Herbicide
NOMENCLATURE:
Common name erbon (E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 2-(2,4,5-trichlorophenoxy)ethyl 2,2-dichloropropionate
Chemical Abstracts name 2-(2,4,5-trichlorophenoxy)ethyl 2,2-dichloropropanoate
CASRN[136254] SmilescodeCC(Cl)(Cl)C(=O)OCCOc1cc(Cl)c(Cl)cc1Cl
COMMERCIALISATION:
History Herbicide introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
ModeofactionTotal herbicide.
PRODUCTS:
Discontinued products Daron* (DowElanco).
Toxicity Class WHO (a.i.) O ECClassification Xn; R22| N; R51, R53
232 erbon
ESBP
Fungicide
NOMENCLATURE:
Common name ESBP (JMAF)
IUPACname S-benzyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-ethyl S-(phenylmethyl) phenylphosphonothioate
CASRN[21722850] SmilescodeCCOP(=O)(SCc1ccccc1)c2ccccc2
COMMERCIALISATION:
History Fungicide introduced by Nissan Chemical Industries Ltd.
PRODUCTS:
Discontinued products Inezin* (Nissan).
etacelasil
NOMENCLATURE:
Common name etacelasil (BSI, E-ISO, (m) F-ISO)
IUPACname 2-chloroethyltris(2-methoxyethoxy)silane
Chemical Abstracts name 6-(2-chloroethyl)-6-(2-methoxyethoxy)-2,5,7,10-tetraoxa-6-
silaundecane CASRN[37894465] ECno2537047 DevelopmentcodesCGA 13
586 SmilescodeCOCCO[Si](CCCl)(OCCOC)OCCOC
PHYSICAL CHEMISTRY: Mol. wt. 316.9 M.f. C11H25ClO6Si Form Colourless liquid.
B.p. 85C /0.001 mmHg V.p. 27 mPa (20C) Henry 3.42 104 Pa m3 mol1 (calc.)
S.g./density 1.10 (20C) Solubility In water 25 g/l (20C). Miscible with benzene,
methanol, hexane, dichloromethane and n-octanol. Stability On hydrolysis, DT50 (calc.,
20C) 50 min (pH 5), 160 min (pH 6), 43 min (pH 7), 23 min (pH 8).
COMMERCIALISATION:
History Abscission agent reported by J. Rufener & D. Piet (Riv. Ortoflorofruttic. Ital.,
1974, 4, 274). Introduced by Ciba-Geigy AG. Patents BE 773498; GB 1371804
APPLICATIONS:
ModeofactionAbscission agent which loosens fruit because of its ethylene-releasing
activity. Uses Loosening of olive fruit, which were then removed by mechanical shaking.
Formulation types SC. SL . Compatibility Not to be applied to trees recently sprayed
with copper fungicides or other pesticides containing stickers or surfactants.
PRODUCTS:
Discontinued products Alsol* (Ciba-Geigy).
etacelasil 233
ANALYSIS:
Product analysis by glc. Residues determined by glc with MCD.
for rats >3100 mg/kg. Slight irritant to skin, not irritating to eyes (rabbits). Inhalation LC50
(4 h) for rats >3.7 mg/l air. NOEL (90 d) for rats 20 mg/kg daily, for dogs 10 mg/kg daily.
Toxicity Class WHO (a.i.) III ECClassification R61| Xn; R22, R48/22
ECOTOXICOLOGY:
Birds Non-toxic to birds. Fish LC50 (96 h) for rainbow trout, crucian carp, bluegill sunfish
>100 mg/l.
etaconazole
Fungicide
FRAC3, G1; SBI Class I, DMI: triazole
NOMENCLATURE:
Common name (taconazole) ((m) F-ISO); etaconazole (BSI, E-ISO)
IUPACname ()-1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-
triazole
Chemical Abstracts name 1-[[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]
methyl]-1H-1,2,4-triazole CASRN[60207934] unstated stereochemistry, formerly
[71245233] DevelopmentcodesCGA 64 251
SmilescodeCCC1COC(Cn2cncn2)(O1)c3ccc(Cl)cc3Cl
PHYSICAL CHEMISTRY: Mol. wt. 328.2 M.f. C14H15Cl2N3O2 Form Colourless
crystals. M.p.7593C (depending on ratio of stereoisomers) V.p. 0.031 mPa (20C)
80 mg/l (20C). In acetone 300, dichloromethane 700, hexane 7.5, methanol 400,
isopropanol 100, toluene 250 (all in g/kg, 20C). Stability Stable to hydrolysis, and at
<350C.
COMMERCIALISATION:
History Fungicide reported by T. Staub etal. (Abstr. Int. Congr. Plant Protect., 1979, p. 310).
Introduced by Ciba-Geigy AG as an agricultural fungicide, having been invented by Janssen
Pharmaceutica, N.V. Patents GB 1522657; BE 835579
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. ModeofactionSystemic, protective and
curative fungicide. Uses Used against Ascomycetes, Basidiomycetes and Deuteromycetes; it
has no activity on Oomycetes. It is especially active on powdery mildews, rusts, sclerotinia
and Venturia spp. on various crops. Post-harvest treatments are active against Fungi
234 etaconazole
including Diplodia, Geotrichum and Penicillium spp. and others. (J. D.Van Geluwe et al., Abstr.
Int. Congr. Plant Protect., 1979, 495; J. D. Gilpatrick, ibid., p. 312). Formulation types WP.
PRODUCTS:
Discontinued products Sonax* (Ciba-Geigy); Vangard* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with TID. Residues determined by glc with FID.
>3100 mg/kg. Slight skin and eye irritant (rabbits). Toxicity Class WHO (a.i.) III
etem
Fungicide
S N
S
N
An oxidation product of nabam (q.v.) (C. W. Pluijgers et al., Tetrahedron Lett., 1971,
1371; W. R. Benson et al., J. Assoc. Off. Anal. Chem., 1972, 55, 44; M. Alvarez et al.,
Tetrahedron Lett., 1973, 939). Also identified as one of the oxidation products of other
ethylenebis(dithiocarbamates), e.g. maneb and zineb (R. A. Ludwig et al., Can. J. Bot., 1955,
33, 42).
NOMENCLATURE:
Common name ETM for (ii) (JMAF); etem for (i) (BSI); etem* for (ii) (BSI, before 1974)
IUPACname (i) 5,6-dihydro-[3H]-imidazo[2,1-c]-[1,2,4]-dithiazole-3-thione; (ii)
1,3,6-thiadiazepane-2,7-dithione; ethylenethiuram monosulfide
Chemical Abstracts name (i) 5,6-dihydro-3H-imidazo[2,1-c]-1,2,4-dithiazole-3-thione;
(ii) hexahydro-1,3,6-thiadiazepine-2,7-dithione CASRN[33813206] (i); [5782832] (ii)
ECno2516844 DevelopmentcodesUCP/21
PHYSICAL CHEMISTRY:
Composition Tech. may be contaminated by sulfur. Mol. wt. 176.3 (i); 178.3 (ii)
M.f. C4H4N2S3 (i); C4H6N2S3 (ii) Form Yellow crystalline powder. M.p.121124C
COMMERCIALISATION:
History Fungicide originally believed to be (ii), later corrected to (i). Evaluated by
Universal Crop Protection Ltd.
PRODUCTS:
Discontinued products Vegita* (Hokko, Kumiai).
etem 235
ANALYSIS:
Residue analysis is by glc (W. H. Newsome, J. Agric. Food Chem., 1975, 23, 348) or by
polarography (R. Engst & W. Schnaak, Z. Lebensm.-Unters. -Forsch., 1970, 144, 81).
ethidimuron
Herbicide
O
N N
C
CH3NH N SO2CH2CH3
S
CH3
HRACC2 WSSA 7; urea

NOMENCLATURE:
Common name ethidimuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(5-ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
Chemical Abstracts name N-[5-(ethylsulfonyl)-1,3,4-thiadiazol-2-yl]-N,N-
dimethylurea Other names sulfodiazol CASRN[30043493] ECno2500106
DevelopmentcodesMET 1486; BAY 107033
SmilescodeCCS(=O)(=O)c1nnc(s1)N(C)C(=O)NC
PHYSICAL CHEMISTRY: Mol. wt. 264.3 M.f. C7H12N4O3S2 Form Colourless crystals.
M.p.155.9156C B.p. Decomposes on distillation V.p. 8 105 mPa (20C) Kow logP
= 0.43 Henry 7.05 10-9 Pa m3 mol1 (calc.) Solubility In water 3 g/l (20C). In hexane
<0.1, toluene 0.11.0, methanol 2, isopropanol 6, dichloromethane 106, chloroform 108,
acetone 150, acetonitrile 240 (all in g/kg, 20C). Stability Stable in aqueous neutral and
acidic media, but unstable in alkaline media. Decomposes at 217C.
COMMERCIALISATION:
History Herbicide reported by L. Eue etal. (C. R. Journ. Etud. Herbic. Conf. COLUMA, 4th,
1973, 1, 14). Introduced by Bayer AG. Patents BE 743615
APPLICATIONS:
site. ModeofactionNon-selective herbicide, absorbed predominantly by the roots.
Uses Total herbicidal control on uncultivated land at 7 kg/ha, and in sugar cane plantations.
Formulation types WP; SC.
PRODUCTS:
Discontinued products Ustilan* (Bayer); Discontinuedmixtures Novorail*
(+amitrole +diuron) (CFPI).
236 ethidimuron
ANALYSIS:
Product analysis by i.r. spectrometry. Residues determined by glc with TID (H. J. Jarczyk,
Pflanz.-Nachr. Bayer (Engl. Ed.), 1979, 32, 186).
Oral Acute oral LD50 for rats >5000, mice >2500, male dogs >5000 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >1000 mg/kg. Non-irritating to skin and
eyes. Inhalation LC50 (4 h) for rats, mice, and hamsters >0.24 mg/l air.
NOEL (90 d) for rats >1000 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation)
IV ECClassification R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 300400, canaries 1000 mg/kg. Fish LC50 (96 h)
for golden orfe >1000, goldfish 400500, carp 200300 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 c.34 months.
ethiolate
Herbicide
NOMENCLATURE:
Common name ethiolate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname S-ethyl diethylthiocarbamate
Chemical Abstracts name S-ethyl diethylcarbamothioate CASRN[2941551]
SmilescodeCCSC(=O)N(CC)CC
PHYSICAL CHEMISTRY: Mol. wt. 161.3 M.f. C7H15NOS
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Chemicals Co.
PRODUCTS:
Discontinuedmixtures Prefox* (+cyprazine) (Gulf).
EHC 76 (1988); a general review of thiocarbamates.
ethiolate 237
ethirimol
Fungicide
CH3 N NHCH2CH3
CH3(CH2)3 N
OH
FRAC8, A2
NOMENCLATURE:
Common name ethirimol (BSI, E-ISO); (thyrimol) ((m) F-ISO)
IUPACname 5-butyl-2-ethylamino-6-methylpyrimidin-4-ol
Chemical Abstracts name 5-butyl-2-(ethylamino)-6-methyl-4(1H)-pyrimidinone
(C.A. preferred tautomer) CASRN[23947606] ECno2459493
DevelopmentcodesPP149 (ICI) SmilescodeCCCCc1c(C)nc(NCC)nc1O
PHYSICAL CHEMISTRY:
Composition Tech. material is 97% pure. Mol. wt. 209.3 M.f. C11H19N3O
Form Colourless crystals. M.p.159160C (phase change atc.140C) V.p. 0.267 mPa
(25C) Kow logP = 2.3 (pH 7, 20C) Henry 2 104 (pH 5.2); 4 104 (pH 7.3); 4
104 (pH 9.3) Pa m3 mol1 (20C) S.g./density 1.21 (25C) Solubility In water 253 (pH
5.2), 150 (pH 7.3), 153 (pH 9.3) (all in mg/l, 20C). In chloroform 150, ethanol 24, acetone
5 (all in g/kg, 20C). Stability Stable to heat, and in acidic and alkaline solutions in the
dark. Aqueous solution exposed to sunlight and air had DT50c.21 d. pKa 5, weak base
(K. Chamberlain et al., Pestic. Sci., 1996, 47, 265 and ref. therein).
COMMERCIALISATION:
History Fungicide reported by R. M. Bebbington etal. (Chem. Ind. (London), 1969, p. 1512).
Introduced by ICI Plant Protection Division (later Syngenta AG) and first marketed in 1970.
Patents GB 1182584 Manufacturers Syngenta; Zhejiang Heyi
APPLICATIONS:
Biochemistry Inhibits nucleic acid synthesis (adenosine deaminase).
ModeofactionSystemic fungicide with protective and curative action. Absorbed by the
roots and leaves, with translocation in the xylem, but not in the phloem. Uses Control of
powdery mildew on barley, wheat, and oats. Applied as a seed dressing, at 4 g/1000 g seed,
a foliar spray, at 250350 g/ha, or to the soil in the root zone. Also used for control of
powdery mildews on cucurbits. Formulation types EC; LS; SC.
PRODUCTS:
Discontinued products Milcurb Super* (Zeneca); Milgo* (Zeneca); Milstem* (Zeneca);
Discontinuedmixtures Ferrax* (+flutriafol +thiabendazole) (seed) (Cheminova,
Syngenta); Halley* (+hexaconazole) (Zeneca).
238 ethirimol
ANALYSIS:
Product analysis by glc of a derivative (CIPACHandbook, 1988, D, 72; J. E. Bagness & W. G.
Sharples, Analyst (London), 1974, 99, 225). Residues in crops determined by glc and in water
by hplc or by spectrometry (M. J. Edwards, Anal. Methods Pestic. Plant Growth Regul., 1976,
8, 285).
Oral Acute oral LD50 for female rats 6340, mice 4000, female guinea pigs 5001000, male
rabbits 10002000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg.
Mild eye irritant; non-irritating to skin (rats). Not a skin sensitiser (guinea pigs).
Inhalation LC50 for rats >4.92 mg/l. NOEL (2 y) for rats 200 mg/kg diet, for dogs 30 mg/
kg daily. Not carcinogenic or teratogenic. ADI/RfD (BfR) 0.1 mg/kg b.w. [1989]; (EPA) 0.05
mg/kg b.w. Toxicity Class WHO (a.i.) U EPA (formulation) IV ECClassification Xn; R21
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 4000 mg/kg. Fish LC50 (96 h) for young brown trout 20,
rainbow trout 66 mg/l. Daphnia LC50 (48 h) 53 mg/l. Bees LD50 (oral) 1.6 mg/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, metabolism involves hydroxylation of
the butyl group. Elimination is in the urine. Plants In plants, ethirimol undergoes rapid
degradation; 2-amino-5-butyl-6-hydroxy-4-methylpyrimidine is found as a metabolite. DT50
in plantsc.3 d. Soil/Environment Soil DT50 14140 d (o.m. 1.010.1%, pH 7.88.1).
ethoate-methyl
IRAC1B
NOMENCLATURE:
Common name ethoate-methyl (BSI, E-ISO); (thoate-m) (F-ISO)
IUPACname S-ethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-ethylacetamide
Chemical Abstracts name S-[2-(ethylamino)-2-oxoethyl] O,O-dimethyl
phosphorodithioate CASRN[116018] ECno2041211 DevelopmentcodesB/77
SmilescodeCCNC(=O)CSP(=S)(OC)OC
COMMERCIALISATION:
History Insecticide and acaricide reported by G. Lemetre etal. (Not. Mal. Piante, 1963, No.
64). Introduced by Bombrini Parodi-Delfino (later Snia Viscosa).
ethoate-methyl 239
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact and systemic
insecticide and acaricide.
PRODUCTS:
Discontinued products Fitios* (Snia Viscosa).
Toxicity Class WHO (a.i.) O ECClassification Xn; R21/22
ethylene bis(trichloroacetate)
Herbicide
NOMENCLATURE:
IUPACname ethylene bis(trichloroacetate)
Chemical Abstracts name 1,2-ethanediyl bis(trichloroacetate) Other names
ethylene glycol bis(trichloroacetate) CASRN[2514536] ECno2197329
SmilescodeClC(Cl)(Cl)C(=O)OCCOC(=O)C(Cl)(Cl)Cl
COMMERCIALISATION:
History Herbicide introduced by Hooker Chemical Corp. (and later by Nor-Am).
APPLICATIONS:
ModeofactionTotal herbicide.
PRODUCTS:
Discontinued products Glytac* (Hooker).
Toxicity Class WHO (a.i.) O ECClassification Xi; R38
ethylene dichloride
Insecticide
ClCH2CH2Cl
IRAC8A
NOMENCLATURE:
Common name dichlorure d(thyl) (F-ISO, accepted in lieu of a common name); EDC
(JMAF); ethylene dichloride (BSI, E-ISO, ESA, accepted in lieu of a common name)
IUPACname 1,2-dichloroethane (I)
240 ethylene dichloride


SmilescodeClCCCl
PHYSICAL CHEMISTRY: Mol. wt. 99.0 M.f. C2H4Cl2 Form Colourless liquid, with
a chloroform-like odour. M.p.-36C B.p. 83.5C V.p. 10.4 kPa (20C) Henry 2.39
102 Pa m3 mol1 (calc.) S.g./density 1.2569 (20C) Solubility In water 4.3 g/l (room
temperature). Soluble in most organic solvents. F.p. 1215C (Abel Pensky); lower and
upper limits of flammability in air 275 and 700 mg/l
COMMERCIALISATION:
History Reported as a component of insecticidal fumigants by R. T. Cotton & R. C. Roark
(J. Econ. Entomol., 1927, 20, 636).
APPLICATIONS:
ModeofactionFumigant insecticide. Uses An insecticidal fumigant used mainly in stored
products.
PRODUCTS:
Discontinued products EDC* (Toyo).
ANALYSIS:
Product analysis by glc (AOACMethods, 18th Ed., 966.05). Residues in stored cereals
determined by glc with ECD (ibid., 977.18; K. A. Scudamore, Anal. Methods Pestic. Plant
Growth Regul., 1988, 16, 207, 231; Analyst (London), 1974, 99, 570; Anal. Methods Residues
Pestic., 1988, Part I). Methods reviewed by J. L. Daft in Comp. Anal. Profiles,Chapter11.
EHC 176 (1995). JMPR Evaln. 33 (1979). CAG. HSG 55 (1991). ICSC.250 (1995). IARC 20
(1979); 71 (1999). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 87/181/EEC.
IARC Class 2B
Oral Acute oral LD50 for rats 670890, mice 870950, rabbits 860970 mg/kg.
ADI/RfD (JMPR) No ADI [1994]. Water GV 0.03 mg/l (see note on carcinogens).
Toxicity Class WHO (a.i.) FM ECClassification F; R11| Xn; R22| Xi; R36/37| N; R52,
R53| concn. dep. PIC Yes.
N-ethylmercurio-4-toluenesulfonanilide
Fungicide
NOMENCLATURE:
IUPACname N-ethylmercurio-4-toluenesulfonanilide; N-(ethylmercury)-p-
toluenesulfonanilide
Chemical Abstracts name ethyl(4-methyl-N-phenylbenzenesulfonamidato-N)mercury
CASRN[517168] SmilescodeCC[Hg]N(c1ccccc1)S(=O)(=O)c2ccc(C)cc2
N-ethylmercurio-4-toluenesulfonanilide 241
PHYSICAL CHEMISTRY: Mol. wt. 476.0 M.f. C15H17HgNO2S

COMMERCIALISATION:
History Fungicide introduced by E. I. du Pont de Nemours & Co.
PRODUCTS:
Discontinued products Ceresan M* (DuPont); Granosan M* (DuPont).
N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
NHCONH
N N
CH2CH3
NOMENCLATURE:
IUPACname N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
Chemical Abstracts name N-(1-ethyl-1H-pyrazol-5-yl)-N-phenylurea Other names
azoluron CASRN[4058906] SmilescodeCCn1nccc1NC(=O)Nc2ccccc2
M.p.201202C S.g./density 1.18 (25C) Solubility In water 365 mg/l (25C). In
acetone 20.3, chloroform 2.3 (both in g/l, 25C). Soluble in ethanol; sparingly soluble in
diethyl ether; almost insoluble in benzene and hexane. Stability Stable under normal
conditions. Hydrolysed rapidly in strong acids and alkalis; DT50 (pH 7) 180 d.
COMMERCIALISATION:
History Plant growth regulator introduced by Fahlberg-List to stimulate flower formation
in glasshouse tomatoes.
APPLICATIONS:
Biochemistry Plant growth regulator with cytokinin-like activity, stimulating cell division,
organ formation and cell elongation (i.e. internodes), as well as seed germination.
Uses In combination with gibberellic acid, used to stimulate flower formation in glasshouse
tomatoes, and thus to produce a higher yield of early tomatoes.
242
N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
ANALYSIS:
Product by potentiometric titration with perchloric acid in acetic acid.
Oral Acute oral LD50 for rats 2700 mg/kg. NOEL (90 d) for rats 25 mg/kg daily.
ENVIRONMENTAL FATE:
Plants Degradation in plants probably involves splitting of the urea bond, with
hydroxylation and glycosidation of the aromatic metabolites.
etinofen
Herbicide
NOMENCLATURE:
Common name (tinof) ((m) F-ISO); etinofen (BSI, E-ISO)
IUPACname -ethoxy-4,6-dinitro-o-cresol
Chemical Abstracts name 2-(ethoxymethyl)-4,6-dinitrophenol CASRN[2544947]
SmilescodeCCOCc1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide introduced by C. H. Boehringer Sohn (later Shell Agrar).
PRODUCTS:
Discontinued products Dinethon* (Shell Agrar).
etnipromid
Herbicide
NOMENCLATURE:
Common name etnipromide ((m) F-ISO); etnipromid (BSI, E-ISO)
IUPACname (RS)-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-N-ethylpropionamide
Chemical Abstracts name ()-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-
N-ethylpropanamide CASRN[76120020] unstated stereochemistry
DevelopmentcodesHoe 39 106 SmilescodeCCNC(=O)C(C)Oc1cc(Oc2ccc(Cl)
cc2Cl)ccc1[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide evaluated by Hoechst AG.
etnipromid 243
etrimfos
CH3CH2O S
P(OCH3)2
N O
N
CH3CH2
IRAC1B
NOMENCLATURE:
Common name etrimfos (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(6-ethoxy-2-ethyl-4-pyrimidinyl) O,O-
dimethyl phosphorothioate CASRN[38260547] ECno2538559
DevelopmentcodesSAN 197I SmilescodeCCOc1cc(OP(=S)(OC)OC)nc(CC)n1
PHYSICAL CHEMISTRY: Mol. wt. 292.3 M.f. C10H17N2O4PS Form Colourless oil.
M.p.-3.35C V.p. 6.5 mPa (20C); 18 mPa (30C); 49 mPa (40C) Kow logP >3.3
S.g./density 1.195 (20C) Solubility In water 40 mg/l (2324C). Completely miscible
with acetone, acetonitrile, chloroform, DMSO, ethanol, diethyl ether, ethyl acetate, hexane,
kerosene, methanol, toluene, xylene. Stability Unstable when pure (c. 40% degradation
in 28 d at 4852C), but dilute solutions in non-polar solvents and its formulations are
stable (c. 5% loss in 1 y at 1822C). When stored in the dark at 2224C for 28 d, no
decomposition occurred in hexane, toluene, chloroform, acetone;c.3% decomposition in
methanol;c.12% decomposition in ethyl acetate. Hydrolysis DT50 (25C) 0.4 d (pH 3), 16 d
(pH 6), 14 d (pH 9). High stability to light.
COMMERCIALISATION:
History Insecticide reported by H. J. Knutti & F. W. Reisser (Proc. Br. Insectic. Fungic. Conf.,
5th, 1975, 2, 675). Introduced by Sandoz Agro AG (later Novartis Crop Protection AG).
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of Lepidoptera, Coleoptera,
Diptera, and some Hemiptera at 250750 g/ha on fruit trees (including citrus), vines, olives,
potatoes, vegetables, maize, alfalfa, ornamentals, tobacco. Control of Pyralidae in paddy rice
at 1.01.5 kg/ha. It was also used at 310 mg/kg for control of Lepidoptera, Coleoptera,
mites, and lice in stored products. Phytotoxicity May be phytotoxic to begonias, and, for
EC formulations, to cherries and some varieties of apple. Formulation types DP; EC; GR;
LS; UL . Compatibility Not compatible with pesticides which are strongly alkaline.
PRODUCTS:
Discontinued products Ekamet* (Novartis); Satisfar* (Novartis).
244 etrimfos
ANALYSIS:
Product analysis by glc. Residues determined by glc (Man. Pestic. Residue Anal., pp. 6, 19; Anal.
Methods Residues Pestic., 1988, Part I, M2, M5; J. C. Karpally et al., Anal. Methods Pestic. Plant
Growth Regul., 1980, 11, 125; Analyst (London), 1985, 110, 765).
EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Evaln. I 60
(1990); JMPR Evaln. 39 (1982). EU Status (1107/2009) Not approved, Commission
percutaneous LD50 for rats >5000, male rabbits >500 mg/kg. Inhalation LC50 (1 h) for rats
>200 mg a.i. (as 50% EC)/l air. NOEL (90 d) for rats 9 mg/kg diet; (6 mo) for dogs
12 mg/kg diet; (2 y) for rats 6, dogs 10 mg/kg diet. ADI/RfD (JMPR) 0.003 mg/kg b.w.
[1986]. Toxicity Class WHO (a.i.) II EPA (formulation) III ECClassification Xn; R22| N;
R50, R53| concn. dep.
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for quail 740 mg/kg diet. Fish LC50 (96 h) for carp and guppies
5.5 mg/l, rainbow trout 24 ;g/l. Daphnia LC50 (48 h) 0.0173 mg/l. Algae EC50 (96 h) for
Scenedesmus subspicatus 2.9 mg/l. Bees Toxic to bees by contact.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, etrimfos is rapidly metabolised and
excreted, mainly in the urine. Metabolites include 6-ethoxy-4-hydroxy-2-ethylpyrimidine,
2-ethyl-4,6-dihydroxypyrimidine, 6-ethoxy-4-hydroxy-2-(1-hydroxyethyl)pyrimidine, and
other isomers. Plants In plants, etrimfos undergoes rapid metabolism to 6-ethoxy-4-
hydroxy-2-ethylpyrimidine, and small amounts of 2-ethyl-4,6-dihydroxypyrimidine and other
hydroxylated derivatives. Soil/Environment Soil DT50 310 d (o.c. 2.8%, pH 6.8). The
principal degradation products are 6-ethoxy-4-hydroxy-2-ethylpyrimidine, small amounts of
2-ethyl-4,6-dihydroxypyrimidine and other hydroxylated derivatives, and CO2.
EXD
Herbicide
NOMENCLATURE:
Common name EXD (WSSA)
IUPACname O,O-diethyl dithiobis(thioformate)
Chemical Abstracts name diethyl thioperoxydicarbonate; thioperoxydicarbonic
acid ([(HO)C(S)]2S2) diethyl ester Other names dixanthogen CASRN[502556]
ECno2079444 SmilescodeCCOC(=S)SSC(=S)OCC
PHYSICAL CHEMISTRY: Mol. wt. 242.4 M.f. C6H10O2S4
EXD 245
COMMERCIALISATION:
History Herbicide reported by E. K. Alban & L. McCombs (Proc. North Cent.Weed Control
Conf., 1949, p. 81). Introduced by Roberts Chemicals Inc. and Monsanto Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Herbisan* (Roberts Chemicals); Sulfasan* (Monsanto).
fenaminosulf
Fungicide
NOMENCLATURE:
Common name fenaminosulf (BSI, E-ISO); ph(naminosulf) ((m) F-ISO); DAPA (JMAF)
IUPACname sodium 4-dimethylaminobenzenediazosulfonate
Chemical Abstracts name sodium [4-(dimethylamino)phenyl]diazenesulfonate
CASRN[140567] ECno2054194 DevelopmentcodesBayer 22 555; Bayer 5072
Smilescode[Na+].CN(C)c1ccc(N=NS(=O)(=O)[O-])cc1
PHYSICAL CHEMISTRY: Mol. wt. 251.2 M.f. C8H10N3NaO3S Form Yellowish-brown
powder. Solubility In water 40 g/kg (20C). Soluble in DMF; insoluble in benzene, diethyl
ether, petroleum oils. Stability Stable 200C. Its aqueous solution is intense orange and
is sensitive to light but is stabilised by sodium sulfite; stable in alkaline media.
COMMERCIALISATION:
History Fungicide reviewed by E. Urbschat (Angew. Chem., 1960, 72, 981). Introduced by
Bayer AG. Patents DE 1028828
APPLICATIONS:
Biochemistry Interferes with NADH-ubiquinone reductase (complex I). Uses Applied
to seed or soil for the control of Pythium, Aphanomyces and Phytophthora spp. in soil at
45110 g/100 kg seed (depending on the crop). Formulation types WP.
PRODUCTS:
Discontinued products Dexon* (Bayer); Lesan* (Bayer).
ANALYSIS:
Product analysis by polarography. Residues determined by colorimetry (D. MacDougall,
Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 49).
246 fenaminosulf
Oral Acute oral LD50 for rats 60, guinea pigs 150 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >100 mg/kg. Toxicity Class WHO (a.i.) II
ECClassification T; R25| Xn; R21| N; R52, R53
fenaminstrobin
Acaricide
CF3
N
HN
N
Cl O CO2Me
O
Cl H3C
NOMENCLATURE:
Common name fenaminstrobin (pa ISO)
IUPACname methyl (E)-2-{-[2-(2,4-dichloroanilino)-6-(trifluoromethyl)pyrimidin-4-
yloxy]-o-tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-
(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]--(methoxymethylene)benzeneacetate
CASRN[1257598438] DevelopmentcodesSYP1620
SmilescodeCO\C=C(C(OC)=O)/C1=C(COC2=CC(C(F)(F)F)=NC(NC3=CC=C(Cl)
C=C3Cl)=N2)C=CC=C1
PHYSICAL CHEMISTRY: Mol. wt. 528.3 M.f. C23H18Cl2F3N3O4
fenapanil
Fungicide
NOMENCLATURE:
Common name f(napanil) ((m) F-ISO); fenapanil (BSI, ANSI, E-ISO)
IUPACname ()-2-(imidazol-1-ylmethyl)-2-phenylhexanenitrile; ()--butyl--
phenylimidazole-1-propanenitrile
Chemical Abstracts name -butyl--phenyl-1H-imidazole-1-
propanenitrile CASRN[61019781] DevelopmentcodesRH-2161
SmilescodeCCCCC(Cn1ccnc1)(C#N)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 253.3 M.f. C16H19N3
COMMERCIALISATION:
History Fungicide evaluated by Rohm & Haas Co.
fenapanil 247
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor.
PRODUCTS:
Discontinued products Sisthane* (Rohm & Haas).
fenasulam
Herbicide
NOMENCLATURE:
Common name fenasulam (BSI, E-ISO)
IUPACname methyl 4-[2-(4-chloro-o-tolyloxy)acetamido]phenylsulfonylcarbamate;
methyl (N-4-chloro-o-tolyloxyacetylsulfanilyl)carbamate
Chemical Abstracts name methyl [[4-[[(4-chloro-2-methylphenoxy)acetyl]amino]
phenyl]sulfonyl]carbamate CASRN[78357489] DevelopmentcodesSSH-60
SmilescodeCOC(=O)NS(=O)(=O)c1ccc(NC(=O)COc2ccc(Cl)cc2C)cc1
PHYSICAL CHEMISTRY: Mol. wt. 412.9 M.f. C17H17ClN2O6S
COMMERCIALISATION:
History Herbicide evaluated by Shionogi and Co. Ltd.
fenazaflor
Acaricide
NOMENCLATURE:
Common name fenazaflor (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname phenyl 5,6-dichloro-2-trifluoromethylbenzimidazole-1-carboxylate
Chemical Abstracts name phenyl 5,6-dichloro-2-(trifluoromethyl)-1H-benzimidazole-1-
carboxylate CASRN[14255880] ECno2381349 DevelopmentcodesNC 5016
SmilescodeFC(F)(F)c1nc2cc(Cl)c(Cl)cc2n1C(=O)Oc3ccccc3
COMMERCIALISATION:
History Acaricide reported by D. T. Saggers & M. L. Clark (Nature (London), 1967, 215, 275).
Introduced by Fisons Pest Control Ltd (later Schering Agriculture).
APPLICATIONS:
ModeofactionContact acaricide.
PRODUCTS:
Discontinued products Lovozal* (Schering); Tarzol* (Fisons).
248 fenazaflor
Toxicity Class WHO (a.i.) O ECClassification Xn; R21/22| N; R50, R53
fenchlorazole-ethyl
Herbicide safener
N CO2CH2CH3
Cl N
N
Cl CCl3
NOMENCLATURE:
Common name fenchlorazole (BSI, E-ISO, (m) F-ISO, for the carboxylic acid)
IUPACname ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-
carboxylate
Chemical Abstracts name ethyl 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-
1H-1,2,4-triazole-3-carboxylate CASRN[103112352]; [103112363] acid
ECno4012905 DevelopmentcodesHoe 070542 (Hoechst); Hoe 072829 (acid)
Smilescodeacid:OC(=O)c1nc(n(n1)c2ccc(Cl)cc2Cl)C(Cl)(Cl)Cl;ester:CCOC(=O)
c1nc(n(n1)c2ccc(Cl)cc2Cl)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 403.5; (acid 375.4) M.f. C12H8Cl5N3O2; (acid
C10H4Cl5N3O2) Form White, practically odourless solid. M.p.108112C
V.p. 8.9 104 mPa (20C) (OECD 104) Henry 3.71 104 Pa m3 mol1 (20C, calc.)
S.g./density 1.7 (20C) Solubility In water 0.9 mg/l (pH 4.5, 20C). In n-hexane 2.5,
methanol 27, toluene 270, acetone 360, dichloromethane >500 (all in g/l, 20C).
Stability Aqueous hydrolysis DT50 115 d (pH 5), 5.5 d (pH 7), 0.079 d (pH 9).
COMMERCIALISATION:
History Herbicide safener reported by H. Bieringer etal. (Proc. 1989 Br. Crop Prot. Conf.
- Weeds, 1, 77). Fenchlorazole-ethyl introduced by Hoechst AG (later Bayer CropScience).
Manufacturers Anhui Huaxing; Bayer CropScience
APPLICATIONS:
Biochemistry Fenchlorazole-ethyl synergises the activity of fenoxaprop-ethyl (or
fenoxaprop-P-ethyl) in susceptible species by enhancing de-esterification to the acid,
which is the active form. It also enhances the tolerance of wheat by accelerating the
metabolic breakdown of fenoxaprop, leading to the formation of non-phytotoxic
degradation products (J. C. Hall & G. R. Stephenson, Proc. Br. Crop Prot. Conf. Weeds, 1995,
1, 261; J. C. Hall et al., Proc. 9th IUPACInt. Congr. Pestic. Chem., London, 1998, 5E-005).
ModeofactionApplied to the foliage of wheat in combination with the grass herbicide
fenoxaprop-ethyl or fenoxaprop-P-ethyl, it prevents growth retardation, leaf discoloration,
fenchlorazole-ethyl 249
and chlorosis of the crop. Uses Used as a safener for fenoxaprop-ethyl or fenoxaprop-P-
ethyl in post-emergence control of grass weeds in wheat, durum wheat, rye, and triticale.
EU Status (1107/2009) Considered to be outside the scope of the Directive; considered
not to be a plant protection product.
percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to eyes and skin
(rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) >1.52 mg/l.
NOEL (90 d) for rats 1280, male mice 80, female mice 320, dogs 80 mg/kg diet; (1 y) for
dogs 80 mg/kg diet. ADI/RfD (BfR) 0.0025 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.)
U ECClassification (R40)
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >2400 mg/kg. Fish LC50 (96 h) for rainbow trout
0.08 mg/l. Daphnia LC50 (48 h) 1.8 mg/l. Bees Not harmful to bees; LC50 (48 h)
>300 g/bee.
fenchlorphos
Insecticide
IRAC1B
NOMENCLATURE:
Common name fenchlorphos (BSI, E-ISO, (m) F-ISO, BAN); ronnel (ANSI, Canada, ESA,
and formerly France)
IUPACname O,O-dimethyl O-2,4,5-trichlorophenyl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-(2,4,5-trichlorophenyl) phosphorothioate
CASRN[299843] ECno2060826 DevelopmentcodesDow ET-14; Dow ET-57
SmilescodeCOP(=S)(OC)Oc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 321.5 M.f. C8H8Cl3O3PS Form Colourless
crystalline powder. M.p.Softens 3537C; melts 4042C V.p. 110 mPa (25C)
Solubility In water 40 mg/l (room temperature). Readily soluble in most organic solvents
including refined kerosine. Stability Stable 60C; stable in neutral and acidic media;
hydrolysed by dilute alkali to the demethyl compound.
COMMERCIALISATION:
History Systemic insecticide introduced by Dow Chemical Co. Patents US 2599516, GB
699064.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide. Uses As a
residual spray for the control of flies and other household pests. Also against ectoparasites
of cattle, sheep and pigs; as a pour-on and backrubber application for lice and hornfly
250 fenchlorphos
control on cattle; as a dip against itch-mite (e.g. Psorergates ovis) and other ectoparasites
of sheep. Also against cattle ectoparasites and in various preparations (oils and aerosol
concentrates) as a wound dressing against blowly in livestock and for spot applications for
the control of ticks on cattle. Formulation types AE; EC; PO; SA.
Compatibility Incompatible with alkaline pesticides.
PRODUCTS:
Discontinued products Korlan* (Dow); Nankor* (Dow); Trolene* (Dow).
ANALYSIS:
Residues determined by glc, tlc or paper chromatography (AOACMethods 18th Ed., 970.52).
See also Pestic. Anal. Man., I, 303.
ICSC.975 (1995). EU Status (1107/2009) Never notified to the EU.
Oral Acute oral LD50 for rats 1740 mg/kg. NOEL (2 y) for rats 1.5 mg/kg b.w. (EPA
Tracking). ADI/RfD (JMPR) 0.01 mg/kg b.w. (1968); (EPA) 0.015 mg/kg b.w. [1987].
Toxicity Class WHO (a.i.) II ECClassification Xn; R21/22| N; R50, R53
fenethacarb
Insecticide
NOMENCLATURE:
Common name fenethacarb (BSI, E-ISO); ph(n) ((m) F-ISO)
IUPACname 3,5-diethylphenyl methylcarbamate (I)
Chemical Abstracts name (I) CASRN[30087479] DevelopmentcodesBAS
235I (BASF) SmilescodeCCc1cc(CC)cc(OC(=O)NC)c1
COMMERCIALISATION:
History Insecticide introduced by BASF AG.
APPLICATIONS:
fenethacarb 251
fenfluthrin
Insecticide
F F
F F
Cl
O F
Cl
IRAC3 O
NOMENCLATURE:
2,3,4,5,6-pentafluorobenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Common name fenfluthrin (BSI, E-ISO); fenfluthrine ((f) F-ISO)
IUPACname 2,3,4,5,6-pentafluorobenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethy
lcyclopropanecarboxylate; 2,3,4,5,6-pentafluorobenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-
Chemical Abstracts name (1R-trans)-(pentafluorophenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate CASRN[75867004]
DevelopmentcodesNAK 1654 SmilescodeCC1(C)C(C=C(Cl)Cl)C1C(=O)
OCc2c(F)c(F)c(F)c(F)c2F
PHYSICAL CHEMISTRY: Mol. wt. 389.2 M.f. C15H11Cl2F5O2 Form Colourless
crystals. M.p.44.7C B.p. 130C /0.075 mmHg V.p. 1 mPa (20C) S.g./density 1.38
(20C) Specific rotation []20 16.8 (c = 1, chloroform)
COMMERCIALISATION:
History Insecticide reported by W. Behrenz & K. Naumann (Pflanz.-Nachr. Bayer (Engl. Ed.),
1982, 35, 309). Evaluated by Bayer AG.
APPLICATIONS:
neurons by interaction with the sodium channel. Uses It shows a wide range of insecticidal
activity against pests of stored products and in public hygiene. It has a good knock-down
activity against Diptera, especially Culicidae.
PRODUCTS:
Discontinued products Baynac* (Bayer).
Oral Acute oral LD50 for male rats 90105, female rats 85120, male mice 119, female
mice 150 mg/kg. Skin and eye Acute percutaneous LD50 (24 h) for male ratsc.2500,
female rats 1535 mg/kg. Not a skin sensitiser (guinea-pigs). NOEL (90 d) for rats
200 mg/kg diet, for dogs 100 mg/kg diet Other Not mutagenic to mice.
252 fenfluthrin
fenitropan
Fungicide
NO2 OCOCH3
CH CH2
CH
OCOCH3
NOMENCLATURE:
Common name fenitropan (BSI, E-ISO); f(nitropane) ((m) F-ISO)
IUPACname (1RS,2RS)-2-nitro-1-phenyltrimethylene di(acetate)
Chemical Abstracts name (1R*,2R*)-2-nitro-1-phenyl-1,3-propanediyl diacetate
CASRN[65934943] stated stereochemistry; [65934954] unstated stereochemistry
DevelopmentcodesEGYT 2248 SmilescodeCC(=O)OCC(C(OC(=O)C)c1ccccc1)
[N+](=O)[O-]
M.p.7072C Solubility In water 30 mg/l (20C). In chloroform 1.25, isopropanol 10,
xylene 350 (all in g/l, 20C).
COMMERCIALISATION:
History Fungicide reported by A. Kis-Tams etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1981,
1, 29). Introduced by EGYT Pharmacochemical Works. Patents GB 1561422; US 4160035
APPLICATIONS:
ModeofactionFungicide with contact action. Uses As a seed treatment for cereals,
maize, rice and sugar beet; applied at 48 g/100 cwt seed, or 46 kg/ha as a foliar spray.
Formulation types LS .
PRODUCTS:
Discontinued products Volparox* (EGYT).
Oral Acute oral LD50 for male rats 3237, female rats 3852 mg/kg. NOEL (90 d) for rats
2000 mg/kg diet. Toxicity Class WHO (a.i.) U
fenoprop; fenoprop-butotyl
NOMENCLATURE:
Common name 2,4,5-TP (France (as alternative to ISO name), JMAF and formerly
USSR); silvex (ANSI, WSSA); fenoprop (BSI, E-ISO, (m) F-ISO)
IUPACname ()-2-(2,4,5-trichlorophenoxy)propionic acid
fenoprop; fenoprop-butotyl 253

Chemical Abstracts name ()-2-(2,4,5-trichlorophenoxy)propanoic acid

CASRN[93721] fenoprop, unstated stereochemistry ECno2022712
PHYSICAL CHEMISTRY: Mol. wt. 269.5; (butotyl ester 369.7) M.f. C9H7Cl3O3;
(butotyl ester C15H19Cl3O4) Form Colourless powder. M.p.179181C V.p. Its lower
alkyl esters are slightly volatile; fenoprop-butometyl (2-butoxy-1-methylethyl ester) is
practically non-volatile Solubility In water 140 mg/l (25C). In acetone 180, methanol
134, diethyl ether 98, heptane 0.86 (all in g/kg, 25C). The amine and alkali metal salts
are soluble in water, acetone, lower alcohols; insoluble in aromatic and chlorinated
hydrocarbons and most non-polar organic solvents. Its lower alkyl esters are sparingly
soluble in water; very soluble in most organic solvents. pKa 2.84
COMMERCIALISATION:
History The plant-growth regulating properties of its salts described by M. E. Synerholm
& P. W. Zimmerman (Contrib. Boyce Thompson Inst., 1945, 14, 91). Its esters introduced as
herbicides by Dow Chemical Co. (later DowElanco) and its salts as plant growth regulators
by Amchem Products Inc. (later Rhne-Poulenc Agrochimie).
APPLICATIONS:
ModeofactionSystemic, selective herbicide, absorbed by leaves and stems.
Uses Recommended for brush control at 24 kg a.e./hl; to control aquatic weeds; to
control broad-leaved weeds in maize and sugar cane at lower rates. Sprays of amine
salts (1.4 a.e./hl) were used 714 d before harvest to reduce pre-harvest drop of apples.
Formulation types EC (esters); SL (amine salts).
PRODUCTS:
Discontinued products Fruitone T* (Amchem); Kuron* (Dow).
ANALYSIS:
Product analysis by glc (CIPACHandbook, 1994, F, 292319; ibid., 1985, 1C, 2257); total acids
by titration or by glc (ibid., 1985, 1C, 2121, 2122). Free phenol impurity determined by hplc
(ibid., 1994, F, 362). Residues determined by glc with ECD (R. P. Marquardt, Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 211; Anal. Methods Pestic. Plant Growth Regul.,
1972, 6, 688). See also Pestic. Anal. Man., I, 208, 302.
IARC 41 (1986), Suppl. 7 (1987). EU Status (1107/2009) Not approved, Commission
IARC Class Chlorophenoxy herbicides classified as 2B
Oral Acute oral LD50 for rats 650 mg/kg, 5001000 mg mixed fenprop-butyl or propylene
glycol butyl ether esters/kg,c.3940 mg a.e. (as fenoprop-trolamine)/kg.
Skin and eye Acute percutaneous LD50 for rabbits >3200 mg a.e. (as fenoprop-trolamine)/
kg. Fenoprop, the trolamine salt and undiluted esters are eye irritants. Water GV 9 g/l
Toxicity Class WHO (a.i.) III ECClassification Xn; R22| Xi; R38| N; R50, R53 (acid): Xn;
R20/21/22| Xi; R38| N; R50, R53 (salts)
254 fenoprop; fenoprop-butotyl

fenoxacrim
Insecticide
NOMENCLATURE:
Common name f(noxacrim) ((m) F-ISO); fenoxacrim (BSI, E-ISO)
IUPACname 3,4-dichloro-1,2,3,4-tetrahydro-6-hydroxy-1,3-dimethyl-2,4-
dioxopyrimidine-5-carboxanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)hexahydro-1,3-dimethyl-2,4,6-trioxo-
5-pyrimidinecarboxamide (preferred tautomer) Other names HHP
CASRN[65400988]
SmilescodeCN1C(=O)C(C(=O)Nc2ccc(Cl)c(Cl)c2)C(=O)N(C)C1=O
COMMERCIALISATION:
History Insecticide discovered by Ciba-Geigy AG.
fenoxaprop-ethyl; fenoxaprop
Herbicide
Cl CH3
O
O O CHCO2C2H5
N
HRACA WSSA 1
NOMENCLATURE:
Common name (for acid) f(noxaprop) ((m) F-ISO); (for acid) fenoxaprop (BSI, ANSI,
E-ISO)
IUPACname ethyl ()-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]propionate; ethyl
()-2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionate
Chemical Abstracts name ethyl ()-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]
propanoate CASRN[82110723] fenoxaprop-ethyl (racemate); [66441234]
fenoxaprop-ethyl (unstated stereochemistry); [95617097] fenoxaprop (racemate);
[73519558] fenoxaprop (unstated stereochemistry) ECno2663629 fenoxaprop-ethyl
DevelopmentcodesHoe 033171; Hoe 053022 (acid)
PHYSICAL CHEMISTRY: Mol. wt. 361.8; (acid 333.7) M.f. C18H16ClNO5; (acid
C16H12ClNO5) Form Colourless solid. M.p.8587C V.p. 4.2 103 mPa (20C)
Kow logP = 4.12 S.g./density 1.3 Solubility In water 0.9 mg/l (pH 7, 25C). In acetone
>500, toluene >300, ethyl acetate >200, ethanol, cyclohexane, n-octanol >10 (all in g/
kg, 25C). Stability Fenoxaprop-ethyl is stable for 6 months at 50C. Not sensitive to
sunlight. Decomposed by aqueous acids and alkalis; DT50 >1000 d (pH 5), 100 d (pH 7),
2.4 d (pH 9) (20C).
fenoxaprop-ethyl; fenoxaprop 255

COMMERCIALISATION:
History Herbicide reported by H. Bieringer etal. (Proc. Br. Crop Prot. Conf. Weeds, 1982, 1,
11). The ethyl ester introduced by Hoechst AG (later AgrEvo GmbH).
Manufacturers AgrEvo
APPLICATIONS:
(ACCase). ModeofactionFenoxaprop-ethyl is a selective herbicide with contact and
systemic action, absorbed principally by the leaves, with translocation both acropetally and
basipetally to the roots or rhizomes. Uses Post-emergence control of many annual and
perennial grass weeds (including Sorghum halepense) in soya beans, cotton, sugar beet,
peanuts, potatoes, beans, sunflowers, vegetables, and other broad-leaved crops; and (when
applied with the herbicide safener fenchlorazole-ethyl) annual and perennial grass weeds
and wild oats in wheat, rye, and triticale. Formulation types EC.
PRODUCTS:
Discontinued products Acclaim* (Hoechst); Bugle* (Hoechst); Cheetah* (AgrEvo);
Cheetah R* (AgrEvo); Depon* (AgrEvo); Excel* (AgrEvo); Furore* (AgrEvo); Option*
(AgrEvo); Option II* (AgrEvo); Puma* (AgrEvo); Whip* (AgrEvo); WhipI* (AgrEvo);
Discontinuedmixtures Cheyenne* (+MCPA-2-ethylhexyl) (Hoechst); Fusion*
(+fluazifop-P-butyl) (Zeneca); Horizon* (+fluazifop-P-butyl) (AgrEvo).
ANALYSIS:
For analysis in residues, see Pestic. Anal. Man., II, 180.430.
J. Pesticide Sci. 1992, 17, 1723. EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD50 for male mice 4670, female mice 5490, male rats 2357, female rats
2500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >1000, female rats >2000
mg/kg. Slight irritant to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >511 mg/m3.
NOEL (3 y) for dogs 0.9 mg/kg b.w. (15 ppm). ADI/RfD (EPA) 0.0025 mg/kg b.w. [1986].
Toxicity Class WHO (a.i.) U ECClassification R43| N; R50, R53 (fenoxaprop-ethyl)
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail >5000, bobwhite quail >2510 mg/kg. Fish LC50
(96 h) for river trout 0.48, bluegill sunfish 0.31 mg/l. Daphnia LC50 (48 h) 3.18 mg/l.
Bees LD50 >0.00002 mg/bee
ENVIRONMENTAL FATE:
Plants In plants, fenoxaprop-ethyl is metabolised via fenoxaprop to 6-chloro-2,3-
dihydrobenzoxazol-2-one. Soil/Environment In soil, fenoxaprop-ethyl is rapidly
hydrolysed to fenoxaprop (A. E. Smith J. Agric. Food Chem. 1985, 33, 483); DT50 110 d.
256
fenoxaprop-ethyl; fenoxaprop
fenpiclonil
Fungicide
H
N
Cl Cl CN
FRAC12, E2; phenylpyrrole
NOMENCLATURE:
Common name fenpiclonil (BSI, E-ISO, (m) F-ISO)
IUPACname 4-(2,3-dichlorophenyl)pyrrole-3-carbonitrile
Chemical Abstracts name 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile
CASRN[74738173] DevelopmentcodesCGA 142 705 (Ciba-Geigy)
SmilescodeClc1cccc(c2c[nH]cc2C#N)c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 237.1 M.f. C11H6Cl2N2 Form White crystals.
M.p.144.9151.1C V.p. 1.1 10-2 mPa (25C) Kow logP = 3.86 (25C)
4.8 mg/l (25C). In ethanol 73, acetone 360, toluene 7.2, n-hexane 0.026, n-octanol 41 (all
in g/l, 25C). Stability Not hydrolysed after 6 h at 100C between pH 3 and 9. Stable up
to 250C.
COMMERCIALISATION:
History Fungicide reported by D. Nevill etal. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1,
65). Introduced in Switzerland (1988) by Ciba-Geigy AG (later Syngenta AG).
Patents EP 236272
APPLICATIONS:
Biochemistry Inhibits mitogen-activated protein kinase, in osmotic signal transduction.
ModeofactionSlightly systemic, contact fungicide with long-lasting activity.
Uses Effective against seed-borne pathogens of cereals, especially Fusarium nivale and
Tilletia caries. On non-cereal crops, controls a wide range of seed- and soil-borne fungi
(Alternaria, Ascochyta, Aspergillus, Fusarium, Helminthosporium, Rhizoctonia and Penicillium
spp.). Having a different mode of action, fenpiclonil gives good control of all isolates of
F. nivale, including those resistant to carbendazim and related fungicides. On cereals and
peas, used at 20 g/100 kg seed; on potatoes, at 2050 g/t (depending on target pathogens).
Formulation types DS; FS; WS .
PRODUCTS:
Discontinued products Beret* (Syngenta); Electer* (Novartis); Galbas* (Novartis);
Gambit* (Novartis); Discontinuedmixtures Arena* (+tebuconazole) (seed treatment,
Germany) (Bayer); Larin* (+imazalil +tebuconazole) (seed treatment, Germany)
(Syngenta).
fenpiclonil 257
ANALYSIS:
Residue determination by hplc. Details available from Syngenta.
Oral Acute oral LD50 for rats, mice, and rabbits >5000 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Non-
sensitising (guinea pigs). Inhalation LC50 (4 h) for rats >1.5 mg/l air. NOEL for rats 1.25,
mice 20, dogs 100 mg/kg b.w. daily. ADI/RfD (BfR) 0.0125 mg/kg b.w. [1991]. Other Non-
teratogenic and non-mutagenic. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >2510 mg/kg. LC50 for mallard ducks >5620,
bobwhite quail 3976 ppm. Fish LC50 (96 h) for rainbow trout 0.8, carp 1.2, bluegill sunfish
0.76, catfish 1.3 mg/l. Daphnia LC50 (48 h) 1.3 mg/l. Algae LC50 (5 d) for Scenedesmus
subspicatus 0.22 mg/l. Bees Not toxic to honeybees; LD50 (oral and contact) >5 g/bee.
Worms LC50 (14 d) for Eisenia foetida 67 mg/kg soil. Other beneficial Harmless to
carabid beetles.
ENVIRONMENTAL FATE:
Animals Rapidly absorbed from the gastrointestinal tract into the general circulation;
rapidly excreted and almost completely eliminated, mostly in the faeces. The dominant
metabolic pathway is oxidation of the pyrrole ring at the 2-position. A minor pathway
is hydroxylation of the phenyl ring. All metabolites are excreted as conjugates, mainly as
glucuronides. Plants Degradation proceeds via oxidation of the pyrrole ring followed by
hydrolysis of the nitrile group. Opening of the pyrrole ring and hydroxylation of the phenyl
ring are further degradation steps. The parent is, however, the relevant residue; between
1315 minor metabolites were also observed. Soil/Environment Relatively persistent
in soil; formation of bound residues represents the major route for dissipation. In leaching
and adsorption/desorption experiments, the compound proved to be immobile in soil,
RMF 0.3. Photolytic DT50 in water 70 min.
fenpirithrin
Insecticide
IRAC3
NOMENCLATURE:
Common name fenpirithrin (BSI, ANSI, E-ISO); fenpirithrine ((f) F-ISO)
IUPACname (RS)-cyano(6-phenoxy-2-pyridyl)methyl (1RS)-cis-trans-3-(2,2-
dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; (RS)-cyano(6-phenoxy-2-pyridyl)
methyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name cyano(6-phenoxy-2-pyridinyl)methyl 3-(2,2-dichloroethenyl)-
258 fenpirithrin
2,2-dimethylcyclopropanecarboxylate CASRN[68523182] unstated stereochemistry

DevelopmentcodesDowco 417
SmilescodeCC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c2cccc(Oc3ccccc3)n2
COMMERCIALISATION:
History Insecticide evaluated by Dow Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Vivithrin* (Dow).
fenridazon
Cl
O
N C
N OH
CH3 O
NOMENCLATURE:
Common name fenridazon (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname 1-(4-chlorophenyl)-1,4-dihydro-6-methyl-4-oxopyridazine-3-carboxylic acid
Chemical Abstracts name 1-(4-chlorophenyl)-1,4-dihydro-6-methyl-4-oxo-3-
pyridazinecarboxylic acid CASRN[68254104]; [83588436] potassium salt
DevelopmentcodesRH-0007 SmilescodeCc1cc(=O)c(nn1c2ccc(Cl)cc2)C(=O)O
COMMERCIALISATION:
History Plant growth regulator evaluated by Rohm & Haas Co.
PRODUCTS:
Discontinued products Hybrex* (potassium salt) (Monsanto).
ANALYSIS:
Residues by hplc/uv (Resid. Anal. Methods).
NOEL (3 generation) for rats 100 ppm (5 mg/kg b.w.) (EPA Tracking). ADI/RfD (EPA)
0.05 mg/kg b.w. [1994].
fenridazon 259
fenson
Acaricide
NOMENCLATURE:
Common name f(nizon) ((m) France); fenson (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname 4-chlorophenyl benzenesulfonate (I)
Chemical Abstracts name (I) Other names CPBS; PCPBS CASRN[80386]
SmilescodeClc1ccc(OS(=O)(=O)c2ccccc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 268.7 M.f. C12H9ClO3S Form Colourless crystals;
(tech. is a pale pink powder). M.p.6162C; (tech., 5659C) Solubility Sparingly soluble
in water. Soluble in organic polar and aromatic solvents. Stability Hydrolysed by alkali.
COMMERCIALISATION:
History Introduced by Murphy Chemical Ltd (later DowElanco).
APPLICATIONS:
ModeofactionContact acaricide. Uses Acaricide with ovicidal properties which was
normally used in combination with acaricides effective against the active stages of mites, to
control mites on apples and glasshouse crops, including vines. Formulation types WP.
PRODUCTS:
Discontinued products Murvesco* (Murphy).
ANALYSIS:
Product analysis by hydrolysis to 4-chlorophenol which is determined by acid-base titration
(CIPACHandbook, 1970, 1, 392). Residues determined by colorimetry of a derivative (A. H.
Kutschinski & E. N. Luce, Anal. Chem., 1952, 24, 1188).
for rats and rabbits >2000 mg/kg. Toxicity Class WHO (a.i.) III ECClassification Xn;
R22| Xi; R36| N; R51, R53
260 fenson
fensulfothion
S
P(OCH2CH3)2
CH3SO O
IRAC1B
NOMENCLATURE:
Common name fensulfothion (BSI, E-ISO, (m) F-ISO, ESA, Society of Nematologists USA)
IUPACname O,O-diethyl O-4-methylsulfinylphenyl phosphorothioate
Chemical Abstracts name O,O-diethyl O-[4-(methylsulfinyl)phenyl]
phosphorothioate Other names DMSP CASRN[115902] ECno2041143
DevelopmentcodesBayer 25 141; S 767 SmilescodeCCOP(=S)(OCC)Oc1ccc(cc1)
S(=O)C
PHYSICAL CHEMISTRY: Mol. wt. 308.4 M.f. C11H17O4PS2 Form Yellowish-brown oil.
M.p.<25C (Agchem. Desk Ref.) B.p. 138141C /0.01 mmHg V.p. 4 mPa (US EPA, cited
in ARS PPD) Kow logP = 2.23 (Agchem. Desk Ref.) S.g./density 1.202 (20C) Solubility
In water 1.54 g/l (25C). Miscible with most organic solvents, except aliphatics. Stability
Subject to hydrolysis in alkaline media. Readily oxidised to the sulfone, and isomerises
readily to the O,S-diethyl isomer (E. Benjamini et al., J. Econ. Entomol., 1959, 52, 94, 99).
COMMERCIALISATION:
History Nematicide reported by B. Homeyer (Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-
Dahlem, 1967, 121, 50). Introduced by Bayer AG. Patents DE 1101406; US 3042703
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNematicide and insecticide
with primarily contact action, but also some systemic activity. Uses Soil application for
control of root-knot, cyst-forming, and free-living nematodes, and also soil-dwelling insects
in cereals, maize, sorghum, cotton, rice, coffee, cocoa, peanuts, soya beans, sugar beet,
sugar cane, tomatoes, potatoes, sweet potatoes, oranges, strawberries, bananas, pineapples,
tobacco, ornamentals, and turf. Formulation types DP; GR; SL; SC. WP.
PRODUCTS:
Discontinued products Dasanit* (Bayer); Terracur* (Bayer); Terracur P* (Bayer).
ANALYSIS:
Product analysis by hplc with uv detection (AOACMethods, 18th Ed., 983.09;
CIPACHandbook, 1985, 1C, 2126), by glc with uv detection (ibid., 1988, D, 92), or by glc with
FID (AOACMethods, 18th Ed., 986.07). Residues determined by glc (C. A. Anderson, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 253; Man. Pestic. Residue Anal., pp. 3, 6, 8, 1317,
fensulfothion 261
19; Anal. Methods Residues Pestic., 1988, Part I, M2, M5).

EHC 63 (1986) a general review of organophosphorus insecticides. JMPR Evaln. 39 (1982),
41 (1983). PDS 44 (1980). ICSC.406 (2001).
Oral Acute oral LD50 for male rats 4.710.5, female rats 2.2, guinea pigs 9 mg/kg. Skin
and eye Acute percutaneous LD50 (in xylene) for female rats 3.5, male rats 30 mg/kg.
Inhalation LC50 (1 h) for male rats 0.113 mg/l air. NOEL In 16 mo feeding trials, rats
receiving 1 mg/kg diet showed no ill-effects. ADI/RfD (JMPR) 0.0003 mg/kg b.w. [1982];
(EPA) 0.00025 mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) Ia ECClassification T+;
R27/28| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 40 mg/kg. Dietary LC50 (5 d) for bobwhite quail
35, mallard ducks 43 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.12, rainbow trout
8.6, golden orfe 6.8 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, fensulfothion is readily oxidised.
fenteracol
Herbicide
NOMENCLATURE:
Common name fenteracol (BSI, E-ISO, (m) F-ISO)
IUPACname 2-(2,4,5-trichlorophenoxy)ethanol (I)
Chemical Abstracts name (I) Other names TCPE CASRN[2122772]
SmilescodeOCCOc1cc(Cl)c(Cl)cc1Cl
COMMERCIALISATION:
History Herbicide introduced by Budapest Chemical Works.
PRODUCTS:
Discontinued products Klorinol* (Budapest Chemical).
262 fenteracol
fenthiaprop; fenthiaprop-ethyl
Herbicide
NOMENCLATURE:
Common name fenthiaprop (BSI, E-ISO); fentiaprop ((m) F-ISO)
IUPACname ()-2-[4-(6-chloro-1,3-benzothiazol-2-yloxy)phenoxy]propionic acid;
()-2-[4-(6-chlorobenzothiazol-2-yloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[(6-chloro-2-benzothiazolyl)oxy]phenoxy]propanoic
acid CASRN[95721123] fenthiaprop (racemate); [73519503] fenthiaprop (unstated
stereochemistry); [93921165] fenthiaprop-ethyl (racemate); [66441110] fenthiaprop-
ethyl (unstated stereochemistry) DevelopmentcodesHoe 35 609
PHYSICAL CHEMISTRY: Mol. wt. 349.8; (ethyl ester 377.8) M.f. C16H12ClNO4S; (ethyl
ester C18H16ClNO4S) Form Fenthiaprop-ethyl is a crystalline solid.
M.p.5657.5C (ethyl ester) V.p. 5.10 104 mPa (20C, ethyl ester) Solubility Ester: In
water 0.8 mg/l (25C). In acetone, ethyl acetate, toluene >500 g/kg, cyclohexane >40 g/kg,
ethanol, n-octanol >50 g/l.
COMMERCIALISATION:
History Herbicide reported by R. Handte etal. (Proc. Br. Crop Prot. Conf. Weeds, 1982, 1,
19). Ethyl ester, fenthiaprop-ethyl, introduced by Hoechst AG.
APPLICATIONS:
ModeofactionLocal and systemic herbicide; translocated acropetally and basipetally to
roots and rhizomes, where the growing points are destroyed. Uses A post-em. herbicide,
active against many annual and perennial grasses. It controls Alopecurus myosuroides, Avena
spp. and volunteer cereals at 180240 g/ha and Agropyron repens at 480720 g/l in oilseed
rape, potatoes and sugar beet. Formulation types EC.
PRODUCTS:
Discontinued products Joker* (ethyl ester) (Hoechst).
1170 mg/kg. Skin and eye Acute percutaneous LD50 for female rats 2000 mg/kg. Slight
irritant to skin and eyes (rabbits). NOEL (90 d) for rats 50 mg/kg diet.
fenthiaprop; fenthiaprop-ethyl 263

fentrifanil
Acaricide
NOMENCLATURE:
Common name fentrifanil (BSI, E-ISO, (m) F-ISO); hexafluoramin (Republic of South
Africa)
IUPACname N-(6-chloro-,,-trifluoro-m-tolyl)-,,-trifluoro-4,6-dinitro-o-toluidine;
2-chloro-2,4-dinitro-5,6-bis(trifluoromethyl)diphenylamine
Chemical Abstracts name N-[2-chloro-5-(trifluoromethyl)phenyl]-2,4-dinitro-6-
(trifluoromethyl)benzenamine CASRN[62441547] DevelopmentcodesPP199
Smilescode[O-][N+](=O)c1cc([N+](=O)[O-])c(Nc2cc(ccc2Cl)C(F)(F)F)c(c1)C(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 429.7 M.f. C14H6ClF6N3O4
COMMERCIALISATION:
History Acaricide reported by N. Morton etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1977, 2,
349). Evaluated by ICI Plant Protection Div. (later ICI Agrochemicals).
APPLICATIONS: Uses Effective against Panonychus ulmi, Tetranychus spp. and eriophyid
mites on apples.
fenuron
Herbicide
NHCON(CH3)2
HRACC2 WSSA 7; urea

NOMENCLATURE:
Common name fenidim* (former exception, USSR); no name (Portugal, Sweden);
fenuron (BSI, E-ISO, F-ISO, ANSI, WSSA)
IUPACname 1,1-dimethyl-3-phenylurea
Chemical Abstracts name N,N-dimethyl-N-phenylurea Other names PDU
CASRN[101428] SmilescodeCN(C)C(=O)Nc1ccccc1
M.p.133134C V.p. 21 mPa (60C) S.g./density 1.08 (20C) Solubility In water
3.85 g/l (25C). In ethanol 108.8, diethyl ether 5.5, acetone 80.2, benzene 3.1, chloroform
125, hexane 0.2, groundnut oil 1.0 (all in g/kg, 2025C). Stability Stable to light and to
oxidation. Stable in neutral media, but hydrolysed by strong acids and alkalis.
COMMERCIALISATION:
History Herbicidal properties of fenuron described by H. C. Bucha & C. W. Todd (Science,
1951, 114, 493). Introduced by E. I. du Pont de Nemours & Co. Patents US 2655447,
264 fenuron
GB 691403, GB 692589 (all to DuPont) Manufacturers Hermania; MV; United

Phosphorus Ltd
APPLICATIONS:
site. ModeofactionNon-selective systemic herbicide, absorbed predominantly by the
roots, with translocation acropetally in the xylem. Uses Control of woody plants and
deep-rooted perennial weeds, particularly on non-crop land. Often used in combination
with chlorpropham to extend the weed spectrum and range of crops.
PRODUCTS:
Discontinued products Dybar* (DuPont); Kayron* (Krishi Rasayan);
Discontinuedmixtures Atlas Gold* (+chlorpropham +propham) (Atlas); Atlas Red*
(+chlorpropham) (Nufarm UK); Croptex Chrome* (+chlorpropham) (Hortichem).
ANALYSIS:
Product analysis of fenuron based on hydrolysis (W. K. Lowen & H. M. Baker, Anal. Chem.,
1952, 24, 1476). Residues determined by colorimetry (R. L. Dalton & H. L. Pease, J. Assoc. Off.
Agric. Chem., 1962, 45, 377).
Oral Acute oral LD50 for rats 6400 mg/kg. Skin and eye Non-irritating to skin.
NOEL In 90 d feeding trials, no apparent effect observed with rats receiving 500 mg/kg
diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Fish LC50 (48 h) for guppies 610 mg/l.
ENVIRONMENTAL FATE:
Plants In plants, N-demethylation occurs step-by-step. Soil/Environment In soil, enzymic
and microbial degradation involves step-by-step N-demethylation.
fenuron-TCA
Herbicide
NOMENCLATURE:
Common name fenuron-TCA (WSSA)
IUPACname 1,1-dimethyl-3-phenyluronium trichloroacetate
Chemical Abstracts name trichloroacetic acid compound with N,N-dimethyl-
N-phenylurea (1:1) CASRN[4482557] DevelopmentcodesGC-2603
SmilescodeCN(C)C(=O)Nc1ccccc1.OC(=O)C(Cl)(Cl)Cl
fenuron-TCA 265
Form Colourless crystals. M.p.6568C Solubility In water 4.8 g/l (room temperature).
In 1,2-dichloroethane 666, trichloroethylene 567 (both in g/kg, room temperature).
Sparingly soluble in petroleum oils.
COMMERCIALISATION:
History Fenuron-TCA introduced by Allied Chemical Corp., Agricultural Division (later
HACCO Inc.). Patents US 2782112, US 2801911 (both to Allied)
APPLICATIONS: Uses Fenuron-TCA combines the herbicidal actions of fenuron and
trichloroacetic acid, and was used for total weed control on non-crop areas and against
woody plants. Formulation types WP.
PRODUCTS:
Discontinued products Dozer* (HACCO); Urab* (HACCO).
Oral Acute oral LD50 for rats 40005700 mg/kg. Skin and eye Skin, eye, and respiratory
tract irritant. Toxicity Class WHO (a.i.) U ECClassification Xi; R38| N; R50, R53
flamprop-methyl; flamprop-isopropyl; flamprop

Herbicide
O CH3
C CHCO2H
N
Cl
HRACZ WSSA 25 F
NOMENCLATURE:
Common name flamprop (assigned to the acid) (BSI, E-ISO, (m) F-ISO, WSSA)
IUPACname methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alaninate; N-benzoyl-N-
(3-chloro-4-fluorophenyl)-DL-alanine (acid)
Chemical Abstracts name N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alanine methyl
ester CASRN[52756259] methyl ester; [52756226] isopropyl ester; [58667633]
acid DevelopmentcodesWL 29671 (methyl ester); WL 29 672 (isopropyl ester) (both
Shell) Smilescodeflamprop:CC(N(C(=O)c1ccccc1)c2ccc(F)c(Cl)c2)C(=O)O
PHYSICAL CHEMISTRY:
Composition Tech is 93%. Mol. wt. methyl ester 335.8; isopropyl ester 363.8; acid 321.7
M.f. C17H15ClFNO3 (methyl ester); C19H19ClFNO3 (isopropyl ester); C16H13ClFNO3
(acid) Form Colourless crystals; (tech., off-white crystals). M.p.8486C; (tech., 81
82C) V.p. Flamprop-methyl: 0.047 mPa (20C) Kow methyl ester, logP = 3.0; acid, logP =
3.09 (25C, unionised, K. Chamberlain et al., Pestic Sci. 47, 265 (1996))
266
flamprop-methyl; flamprop-isopropyl; flamprop
Henry 4.51 104 Pa m3 mol1 (flamprop-methyl, calc.) Solubility Flamprop-methyl:

in water 35 mg/l (20C). In acetone >500, cyclohexanone 414, o-xylene 258, carbon
tetrachloride 168, ethanol 135, hexane 7 (all in g/l, 20C). Stability Stable to light and to
heat, and at pH 27. Hydrolysed in alkaline media (pH >7) to flamprop and methanol.
pKa Acid, 3.7 (K. Chamberlain et al., Pestic. Sci., 1996, 47, 265 and refs. therein)
COMMERCIALISATION:
History Herbicidal properties of flamprop-methyl reported by E. Haddock etal. (Proc. Br.
Weed Control Conf., 12th, 1974, 1, 9); compared with analogues by B. Jeffcoat etal. (Pestic.
Sci., 1977, 8, 1). Flamprop-isopropyl and flamprop-methyl introduced by Shell Research Ltd
(later American Cyanamid Co.); later replaced by the single stereoisomers (flamprop-M-
isopropyl and flamprop-M-methyl). Patents GB 1437711
APPLICATIONS:
Biochemistry Selectivity depends on the rates of hydrolysis to flamprop and detoxication
of the latter by formation of conjugates within the plant; the acid is translocated to
meristems where it inhibits plant growth. ModeofactionFlamprop-methyl is a selective
systemic herbicide, absorbed by the leaves. Undergoes hydrolysis to flamprop, which is
translocated readily to growing points. Uses Post-emergence control of wild Oats (Avena
spp.) in wheat, including crops undersown with clover or grass. Also controls Alopecurus
myosuroides. Formulation types EC. Compatibility If applied together with phenoxy
herbicides, the activity of flamprop-methyl may be reduced.
PRODUCTS:
Discontinued products Barnon* (isopropyl ester) (Cyanamid).
ANALYSIS:
Product analysis by i.r. spectrometry or by glc. Residues determined by glc with ECD.
Oral Acute oral LD50 for rats 1210, mice 720 mg/kg (flamprop-methyl).
Skin and eye Acute percutaneous LD50 for rats >294 mg a.i./kg (as EC formulation). Non-
irritating and non-sensitising to skin. NOEL (2 y) for rats 2.5 mg a.i./kg diet, for dogs 10
mg/kg diet. Other Acute i.p. LD50 for rats 350500 mg/kg. Toxicity Class WHO (a.i.) III
(allocated to the acid)
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 4640, pheasants, mallard ducks, domestic fowl,
partridges, pigeons >1000 mg/kg (flamprop-methyl). Fish LC50 (96 h) for rainbow trout
4.7 mg/l. Bees Non-toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolism and elimination occur
within 4 d. Plants In plants, flamprop-methyl is hydrolysed to the biologically-active
flamprop, which then undergoes conversion to a biologically-inactive conjugate.
flamprop-methyl; flamprop-isopropyl; flamprop 267

fluacrypyrim
Acaricide
O
CF3
CH3 CH CH3
O C O N CH3
CH2 CH
O N O
CH3
IRAC20C
NOMENCLATURE:
Common name fluacrypyrime ((m) F-ISO); fluacrypyrim (BSI, E-ISO)
IUPACname methyl (E)-2-{-[2-isopropoxy-6-(trifluoromethyl)pyrimidin-4-yloxy]-o-
tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)--(methoxymethylene)-2-[[[2-(1-methylethoxy)-
6-(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]benzeneacetate CASRN[229977
939]; [178813815] unspecified stereochemistry DevelopmentcodesNA-83
Smilescodewithout stereochemistry:COC=C(C(=O)OC)c1ccccc1COc2cc(nc(OC(C)
C)n2)C(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 426.4 M.f. C20H21F3N2O5 Form White, odourless
solid. M.p.107.2108.6C V.p. 2.69 103 mPa (20C) (gas saturation method) Kow logP
= 4.51 (pH 6.8, 25C) Henry 3.33 103 Pa m3 mol1 (20C, calc.)
S.g./density 1.276 Solubility In water 3.44 104 g/l (pH 6.8, 20C). In dichloromethane
579, acetone 278, xylene 119, acetonitrile 287, methanol 27.1, ethanol 15.1, ethyl acetate
232, n-hexane 1.84, n-heptane 1.60 (all in g/l, 20C). Stability Stable at pH 4 and 7; DT50
574 d (pH 9). Aqueous photolysis DT50 26 d.
COMMERCIALISATION:
History Acaricide registered in 2001 and launched in 2002, by Nippon Soda Co. Ltd.
Manufacturers Nippon Soda
APPLICATIONS:
Biochemistry Mitochondrial complex III electron transport inhibitor (coupling site II).
ModeofactionAcaricide with contact and stomach action. Uses Control of Panonychus,
at 10 g/100 l, for citrus; Panonychus and Tetranychus, at 15 g/100 l, for apples and pears.
Formulation types SC.
PRODUCTS:
Discontinued products Titaron* (Nippon Soda); Discontinuedmixtures Oonata*
(+chlorfenapyr) (Nippon Soda).
EU Status (1107/2009) Never notified to the EU.
268 fluacrypyrim
percutaneous LD50 for male and female rats >2000 mg/kg. Weakly irritating for eyes; non-
irritating for skin (rabbits). Inhalation LC50 (4 h) for male and female rats >5.09 mg/l.
NOEL (24 mo) for male rats 5.9 mg/kg b.w., for female rats 61.7 mg/kg b.w.; (18 mo) for
male mice 20 mg/kg b.w.., for female mice 30 mg/kg b.w.; (12 mo) for male and female dogs
10 mg/kg b.w.. ADI/RfD (FSC) 0.059 mg/kg b.w.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 for bobwhite quail
>5620 ppm. Fish LC50 (96 h) for carp 0.195 ppm. Daphnia LC50 (48 h) 0.094 ppm.
Algae EbC50 (72 h) for Selenastrum capricornutum 0.0173 ppm; ErC50 (72 h) for
Selenastrum capricornutum 0.14 ppm. Bees LC50 (oral) >300 ppm; LD50 (contact)
>10 g/bee. Worms LC50 for earthworms 23 mg/kg soil. Other beneficial No effect on
Agistemus exsertus at 400 ppm.
fluazolate
Herbicide
Cl F
Br
(CH3)2CHO CF3
O N N
CH3
HRACE WSSA 14; phenylpyrazole herbicide
NOMENCLATURE:
Common name fluazolate (BSI, E-ISO, (m) F-ISO)
IUPACname isopropyl 5-(4-bromo-1-methyl-5-trifluoromethylpyrazol-3-yl)-2-chloro-4-
fluorobenzoate
Chemical Abstracts name 1-methylethyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-
1H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate CASRN[174514079]
DevelopmentcodesMON 48500 (Monsanto); JV 485 SmilescodeCC(C)OC(=O)
c1cc(c2nn(C)c(c2Br)C(F)(F)F)c(F)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 443.6 M.f. C15H12BrClF4N2O2 Form Fluffy, white,
crystalline solid. M.p.79.580.5C V.p. 9.43 103 mPa (20C) Kow logP = 5.44
Henry 7.89 10-2 Pa m3 mol1 (calc.) Solubility In water 53 ;g/l (20C). Stability
Stable at pH 4 and pH 5; DT50 4201 d (pH 7, calc.), 48.8 d (pH 9) (both 20C).
COMMERCIALISATION:
History Reported by S. D. Prosch etal. (Proc. Br. Crop Prot. Conf. Weeds, 1997, 1, 45).
Discovered by Monsanto Co. and evaluated by Twinagro, a j.v. of Monsanto and Bayer AG.
fluazolate 269
Patents US 5489571; US 5587485; WO 9206962 Manufacturers Twinagro

APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionCauses rapid
necrosis shortly after emergence of plants. Uses Under development for use as a pre-
emergence cereal herbicide, controlling grasses such as Alopecurus myosuroides, Lolium spp.,
Apera spica-venti, Poa annua and Phalaris spp., as well as broad-leaved weeds such as Galium
aparine, at 125175 g/ha.
for rats >5000 mg/kg. Slightly irritating to eyes; not irritating to skin (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation LC50 for rats >1.7 mg/l. Other Negative in Ames,
HGPRT/CHO, micronucleus and in vitro cytogenetic tests.
ECOTOXICOLOGY:
Birds Oral LD50 for bobwhite quail and mallard ducks >2130 mg/kg. Dietary LC50 for
bobwhite quail and mallard ducks >5330 mg/kg. Fish LC50 (96 h) for rainbow trout and
bluegill sunfish >0.045 mg/l. Daphnia EC50 (48 h) >0.039 mg/l. Worms LC50 (14 d) for
earthworms >1170 mg/kg dry soil.
ENVIRONMENTAL FATE:
Soil/Environment Laboratory DT50 (3 field and 1 standard soil) 1671 d. Strongly bound
to soil: Kd and Koc in clay loam (pH 5.1, o.c. 1.94%) 2.5 102 and 1.3 104, respy., in loam
(pH 4.7, o.c. 4.24%) 2.9 102 and 0.7 104, in silt loam (pH 6.3, o.c. 0.08%) 1.4 102 and
1.7 104, in loamy sand (pH 5.8, o.c. 1.30%) 2.0 102 and 1.6 104. Concentrations of
fluazolate in lysimeter leachates were <0.01 g/l.
fluazuron
Ixodicide
F
Cl NHCONHCO
N
CF3 O F
IRAC15 Cl
NOMENCLATURE:
Common name fluazuron (BSI, E-ISO, (m) F-ISO, INN)
IUPACname 1-[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-
difluorobenzoyl)urea
270 fluazuron
Chemical Abstracts name N-[[[4-chloro-3-[[3-chloro-5-(trifluoromethyl)-2-

pyridinyl]oxy]phenyl]amino]carbonyl]-2,6-difluorobenzamide CASRN[86811587]
DevelopmentcodesCGA 157 419 (Ciba-Geigy) SmilescodeFc1cccc(F)c1C(=O)
NC(=O)Nc2ccc(Cl)c(Oc3ncc(cc3Cl)C(F)(F)F)c2
PHYSICAL CHEMISTRY: Mol. wt. 506.2 M.f. C20H10Cl2F5N3O3 Form White to pink,
odourless, fine crystalline powder. M.p.219C (decomp.) V.p. 1.2 10-7 mPa (20C)
Kow logP = 5.1 (rp-tlc method) Henry <3.04 106 Pa m3 mol1 (calc.) S.g./density 1.59
(20C) Solubility In water <0.02 ppm (20C). In methanol 2.4, isopropanol 0.9 (both in
g/l, 20C). Stability Stable up to 219C. Hydrolysis DT50 (25C) 14 d (pH 3), 7 d (pH 5),
20 h (pH 7), 0.5 h (pH 9).
COMMERCIALISATION:
History Ixodicide.
Manufacturers Syngenta; E-tong
APPLICATIONS:
Biochemistry Interaction with chitin formation. ModeofactionSystemic acarine
growth regulator with contact and stomach action. Uses Strategic control of the
cattle tick Boophilus microplus (including all known resistant strains) on beef cattle.
Formulation types PO.
PRODUCTS:
Discontinued products Acatak* (Syngenta).
ANALYSIS:
By hplc.
JECFA 48 (1997).
Oral Acute oral LD50 for rats >5000 mg/kg (OECD 401). Skin and eye Acute
percutaneous LD50 for rats >2000 mg/kg (OECD 402). Inhalation LC50 (4 h) for rats
>5994 mg/m3 (OECD 403). NOEL (1 y) for dogs 7.5 mg/kg b.w. daily; (life-time) for rats
400, mice (males and females) 4.5 mg/kg b.w. daily. In 2-generation reproduction tests
(rats), NOEL 100 ppm. No carcinogenic, mutagenic, teratogenic or reprotoxicity potential.
ADI/RfD (JMPR) 0.04 mg/kg b.w. [1997] (JECFA evaluation). Toxicity Class WHO (a.i.) III
(company classification)
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2000 mg/kg. LC50 (8 d) for
bobwhite quail and mallard ducks >5200 ppm. Fish LC50 for rainbow trout >15, carp >9.1
mg/l (OECD class "harmful"). Daphnia LC50 0.0006 mg/l (OECD class "very toxic").
Algae NOEC for freshwater green Algae 27.9 mg/l (virtually non-toxic).
Bees OECD class "not toxic". Worms LC50 (14 d) for earthworms >1000 mg/kg (not
toxic) (OECD 207).
fluazuron 271
ENVIRONMENTAL FATE:
Animals See P. S. Tantiyaswasdikul in "Residues of some veterinary drugs in animal and
foods" FAO Food and Nutrition Papers 41/10 (1998). Plants Not relevant.
Soil/Environment Not investigated; environmental contamination is unlikely because of
pour-on application.
flubenzimine
Acaricide
NOMENCLATURE:
Common name flubenzimine (BSI, E-ISO, (f) F-ISO)
IUPACname (2Z,4E,5Z)-N2,3-diphenyl-N4,N5-bis(trifluoromethyl)-1,3-thiazolidine-2,4,5-
triylidenetriamine
Chemical Abstracts name N-[3-phenyl-4,5-bis[(trifluoromethyl)imino]-2-
thiazolidinylidene]benzenamine CASRN[37893020] unstated stereochemistry
ECno2537031 DevelopmentcodesBAY SLJ 0312 SmilescodeFC(F)(F)
N=C1SC(=Nc2ccccc2)N(C1=NC(F)(F)F)c3ccccc3
PHYSICAL CHEMISTRY: Mol. wt. 416.4 M.f. C17H10F6N4S Form Orange-yellowish
powder. M.p.118.7C V.p. <1 mPa (20C) Henry <2.60 101 Pa m3 mol1 (calc.)
Solubility In water 1.6 mg/l (20C). In dichloromethane, toluene >200, hexane,
isopropanol 510 (all in g/l, 20C). Stability DT50 29.9 h (pH 4), 30 min (pH 7), 10 min
(pH 9) (22C).
COMMERCIALISATION:
History Acaricide reported by G. Zoebelein etal. (Mitt. Biol. Bundesanst. Land-
Forstwirtsch., Berlin-Dahlem, 1979, 191, 283; Pflanz.-Nachr. Bayer (Engl. Ed.), 1980, 33, 169).
Introduced by Bayer AG.
APPLICATIONS:
ModeofactionContact acaricide; acting as a mite growth regulator. The developent of
larvae hatching from treated eggs and treated larvae and nymphs is retarded, and they fail
to emerge from the next quiescent stage. Treated adult mites have a shorted life and lay
fewer eggs. Uses Applied early at 500 mg/l, against Panonychus ulmi and Tetranychus spp. on
pome fruit, plums and damsons, also against P. citri, Phyllocoptruta oleivora and Tetranychus
spp. on citrus. Also shows some fungicidal activity. Formulation types WP.
PRODUCTS:
Discontinued products Cropotex* (Bayer).
ANALYSIS:
Residues determined by glc with ECD (G. Drger, ibid., 1981, 34, 180).
272 flubenzimine
Oral Acute oral LD50 for male rats >5000 mg (in acetone +oil)/kg, 2840 mg (in water
+Cremophor EL)/kg, for female rats 37005000 mg (in acetone +oil)/kg, 2685 mg (in
water +Cremophor EL)/kg; for male mice >2500 mg/kg; for female rabbitsc.360 mg/
kg; for female dogs >500 mg/kg. Skin and eye Acute percutaneous LD50 (24 h) for rats
>5000 mg/kg. Not a skin irritant; causes moderate to severe conjunctival irritation to
rabbits. Inhalation (4 h) for rats >0.357 mg a.i. (as 50% WP)/l air. NOEL (90 d) for male
dogs 100 mg/kg diet, for rats 500 mg/kg diet Other Not mutagenic in dominant lethal
assays in mice; not embryotoxic or teratogenic in rabbits. Toxicity Class WHO (a.i.) U
ECClassification Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens >5000, Japanese quail 45005000, canaries >1000 mg/kg.
flucofuron
Insecticide
CF3
Cl NHCONH Cl
CF3
NOMENCLATURE:
Common name flucofuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1,3-bis(4-chloro-,,-trifluoro-m-tolyl)urea
Chemical Abstracts name N,N-bis[4-chloro-3-(trifluoromethyl)phenyl]urea
CASRN[370503] SmilescodeFC(F)(F)c1cc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)
ccc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 417.1 M.f. C15H8Cl2F6N2O
COMMERCIALISATION:
History Insecticide developed by Ciba-Geigy AG.
APPLICATIONS: Uses Insecticide used to control Tineidae larvae, which attack cotton
fabrics.
PRODUCTS:
Discontinued products Mitin N* (Ciba-Geigy).
flucofuron 273
flucycloxuron
F
CH2 NHCONHCO
C N O
F
Cl
IRAC15; benzoylurea
NOMENCLATURE:
Common name flucycloxuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-[-(4-chloro--cyclopropylbenzylideneamino-oxy)-p-tolyl]-3-(2,6-
difluorobenzoyl)urea (ratio 5080% (E)- and 5020% (Z)- isomers)
Chemical Abstracts name N-[[[4-[[[[(4-chlorophenyl)cyclopropylmethylene]amino]
oxy]methyl]phenyl]amino]carbonyl]-2,6-difluorobenzamide CASRN[94050529]
(E)- isomer; [94050530] (Z)- isomer; [113036887] unstated stereochemistry
DevelopmentcodesPH 7023; DU 319722 (both Duphar); UBI-A1335
(Uniroyal) Official codes OMS 3041 SmilescodeFc1cccc(F)c1C(=O)NC(=O)
Nc2ccc(CON=C(C3CC3)c4ccc(Cl)cc4)cc2
PHYSICAL CHEMISTRY:
Composition Ratio 5080% (E)- and 5020% (Z)- isomers. Mol. wt. 483.9
M.f. C25H20ClF2N3O3 Form Off-white to yellow crystals (tech.). M.p.143.6C (decomp.)
(for (E)-, (Z)- isomeric mixture) V.p. 5.4 105 mPa (25C) (for (E)-, (Z)- isomeric
mixture) Kow logP = 6.97 (E)- isomer; 6.90 (Z)- isomer Henry 2.6 10-2 Pa m3 mol1
(25C) Solubility In water <1 ;g/l (20C). In cyclohexane 0.2, xylene 3.3, ethanol 3.8,
N-methylpyrrolidone 940 (all in g/l, 20C) for (E)-, (Z)- isomeric mixture.
Stability Thermally stable, <2% decomposition after 24 hours storage at 50C. No
degradation at pH 5, 7 or 9. Photolytically degraded, DT50c.18 d.
COMMERCIALISATION:
History Acaricide and insecticide reported by A. C. Grosscurt etal. (Pestic. Sci., 1988, 22,
51). Introduced by Duphar B.V. (later Chemtura Corp.) in 1988. Patents EP 117320; US
4550202; US 4609676 Manufacturers Chemtura
APPLICATIONS:
Biochemistry Chitin synthesis inhibitor, type 0 (Lepidopteran). ModeofactionNon-
systemic acaricide and insecticide which inhibits the moulting process in mites and insects.
It is only active against eggs and larval stages. Adult mites and insects are not affected.
Uses Control of eggs and larval stages of eriophyid and tetranychid mite species on a
variety of crops, including fruit crops, vegetables and ornamentals. Also controls larvae
274 flucycloxuron
of a number of insects. Because of its relative selectivity, flucycloxuron is well-suited for

integrated control programmes. Recommended concentration for control of mites on fruit
crops is 0.010.015% a.i. On insects, good activity has been found against codling moth,
leaf miners and some leaf rollers in pome fruit, at the same concentration. In ornamentals
grown under glass/plastic, lower concentrations can be used. In grapes, the recommended
dosage is 125150 g/ha. Formulation types DC.
PRODUCTS:
Discontinued products Andalin* (Uniroyal).
ANALYSIS:
Product and residue analysis by hplc; details available from Chemtura.
rats >2000 mg/kg. Non-irritating to skin; mild eye irritant (rabbits). Inhalation LC50
(4 h) for rats >3.3 mg/l air. NOEL In 2 y feeding trials, NOAEL for rats 120 mg/kg diet. In a
2-generation reproduction study, NOAEL for rats 200 mg/kg diet. Non-mutagenic and non-
teratogenic. No evidence of carcinogenicity. Other Acute i.p. LD50 for rats
2000 mg/kg. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >2000 mg/kg. Dietary LC50 (8 d) for mallard
ducks and bobwhite quail >6000 mg/kg diet. Fish LC50 (96 h) for rainbow trout and
bluegill sunfish >100 mg/l. Daphnia LC50 (48 h) 0.27 g/l. Algae NOEC for Selenastrum
capricornutum >2.2 ;g/l. Other aquatic spp. LC50 (96 h) for mysid shrimps (Mysidopsis
bahia) 340 ng/l. Bees Low toxicity to bees. Contact LD50 for honeybees >100 g/bee.
Worms EC50 (14 d) for earthworms >1000 mg/kg soil. Other beneficial Slightly to
moderately harmful to predatory mites (IOBC).
ENVIRONMENTAL FATE:
Animals Poorly absorbed from gastrointestinal tract; mainly excreted as unchanged
parent compound in the faeces. Flucycloxuron absorbed is metabolised and further
excreted in the urine, mainly as 2,6-difluorobenzoic acid and N-(4-carboxyphenyl)-N-(2,6-
difluorobenzoyl)urea. Plants Non-systemic. Not metabolised on plants.
Soil/Environment Strongly and irreversibly bound by soil/humic acid complex and
virtually immobile in soil. Soil DT50 0.250.5 y.
flucycloxuron 275
fluenetil
NOMENCLATURE:
Common name fluenetil (BSI, E-ISO, (m) F-ISO); flu(n) (France)
IUPACname 2-fluoroethyl biphenyl-4-ylacetate
Chemical Abstracts name 2-fluoroethyl [1,1-biphenyl]-4-acetate CASRN[4301502]
DevelopmentcodesM 2060 SmilescodeFCCOC(=O)Cc1ccc(cc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 258.3 M.f. C16H15FO2 Form Colourless crystals.
M.p.60.5C B.p. 177180C /1 mmHg S.g./density 1.139 (68C) Solubility In water
2.5 mg/l (25C). In acetone >850, acetonitrile 810, benzene 760, ethanol 630, hexane 10,
methanol 80, olive oil <0.7 (all in g/l, 25C). Stability Stable at pH 4, but hydrolysed at pH
7 and rapidly at pH 9.
COMMERCIALISATION:
History Insecticide reported by P. de Pietri-Tonelli etal. (Proc. Br. Insectic. Fungic. Conf., 3rd,
1965, p. 478). Introduced by Montecatini Edison S.p.A. (later Agrimont S.p.A.).
Patents IT 710046; US 3436418
APPLICATIONS:
ModeofactionA selective, non-systemic acaricide and insecticide. Uses Applied in oil at
400600 mg/kg in late winter to control winter eggs of Panonychus ulmi, Bryobia praetiosa,
Aphididae, Psyllidae, some Lepidoptera and the winter stages of scale insects.
PRODUCTS:
Discontinuedmixtures Lambrol* (+petroleum oils) (Montecatini).
ANALYSIS:
Product analysis by glc or by hydrolysis to the corresponding acetic acid which was
measured. Residues determined by glc or by colorimetry.
Oral Acute oral LD50 for rats 8.7, mice 57, monkeys 75 mg/kg. Skin and eye Acute
percutaneous LD50 (10 d) for rabbits 7.5 mg/kg. NOEL (90 d) for rats 0.3 mg/kg daily.
Toxicity Class WHO (a.i.) O ECClassification T+; R27/28
flufenican
Herbicide
NOMENCLATURE:
Common name fluf(nican) ((m) F-ISO); flufenican (BSI, E-ISO)
IUPACname 2-(,,-trifluoro-m-tolyloxy)nicotinanilide
Chemical Abstracts name N-phenyl-2-[3-(trifluoromethyl)phenoxy]-3-
pyridinecarboximide CASRN[78863624]
SmilescodeFC(F)(F)c1cccc(Oc2ncccc2C(=O)Nc3ccccc3)c1
276 flufenican

COMMERCIALISATION:
flufenoxystrobin
Fungicide
Cl
CF3 O
O O
NOMENCLATURE:
C H3 H C H3
Common name flufenoxystrobin (pa ISO)

IUPACname methyl (2E)-2-{2-[(2-chloro-,,-trifluoro-p-tolyloxy)methyl]phenyl}-3-
methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[2-chloro-4-(trifluoromethyl)phenoxy]
methyl]--(methoxymethylene)benzeneacetate
SmilescodeCO\C=C(C(OC)=O)/C1=C(COC2=CC=C(C(F)(F)F)C=C2Cl)C=CC=C1
PHYSICAL CHEMISTRY: Mol. wt. 400.8 M.f. C19H16ClF3O4
flufenprox
Insecticide
Cl
CF3
O
O
CH3CH2O
IRAC3
NOMENCLATURE:
Common name flufenprox (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(4-chlorophenoxy)benzyl (RS)-2-(4-ethoxyphenyl)-3,3,3-trifluoropropyl
ether
Chemical Abstracts name 1-(4-chlorophenoxy)-3-[[2-(4-ethoxyphenyl)-
3,3,3-trifluoropropoxy]methyl]benzene CASRN[107713586]
flufenprox 277
DevelopmentcodesICIA5682
SmilescodeCCOc1ccc(cc1)C(COCc2cccc(Oc3ccc(Cl)cc3)c2)C(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 450.9 M.f. C24H22ClF3O3 Form Odourless,
transparent pale yellow-green liquid. B.p. 204C /0.2 mmHg V.p. 1.3 104 mPa (20C)
S.g./density 1.25 (25C) Solubility In water 2.5 ;g/l (pH 7). Soluble (>500 g/l) in
hexane, toluene, acetone, dichloromethane, ethyl acetate, n-octanol, acetonitrile and
methanol.
COMMERCIALISATION:
History Insecticide reported by R. F. S. Gordon etal. (Proc. Br. Crop Prot. Conf. - Pests Dis.,
1992, 1, 81).
Manufacturers Zeneca
APPLICATIONS:
ModeofactionInsecticide with fast action and residual efficacy. Uses Control of
Homoptera, Heteroptera, Coleoptera and Lepidoptera on rice, including rice hoppers.
Formulation types DL; GR; EW; EC.
rats >2000 mg/kg. Mild skin and eye irritant (rabbits). Skin sensitiser (guinea pigs).
ECOTOXICOLOGY:
Fish LC50 (96 h) for carp >10 mg tech./l, for red killifish and Asian pond loach >10 mg/l as
0.5% dust or granule. Daphnia LC50 for D. pulex (48 h) 0.00035 mg/l. Bees LD50
0.03 g/bee; NOEL 0.002 g/kg. Worms LD50 for Eisenia foetida >1000 mg/kg.
Other beneficial Low toxicity to predatory arthropods.
flumezin
Herbicide
NOMENCLATURE:
Common name flumezin (BSI, E-ISO); flum(zine) ((f) F-ISO)
IUPACname 2-methyl-4-(,,-trifluoro-m-tolyl)-1,2,4-oxadiazinane-3,5-dione
Chemical Abstracts name 2-methyl-4-[3-(trifluoromethyl)phenyl]-2H-1,2,4-oxadiazine-
3,5(4H,6H)-dione CASRN[25475734] DevelopmentcodesBAS 348H (BASF)
SmilescodeCN1OCC(=O)N(C1=O)c2cccc(c2)C(F)(F)F
COMMERCIALISATION:
History Herbicide evaluated by BASF AG.
278 flumezin
flumipropyn
Herbicide
O F
N Cl
CH3
O O CH
C
CH
NOMENCLATURE:
Common name flumipropyne ((m) F-ISO); flumipropyn (BSI, E-ISO)
IUPACname ()-N-[4-chloro-2-fluoro-5-(1-methylprop-2-ynyl)oxyphenyl]cyclohex-1-
ene-1,2-dicarboximide
Chemical Abstracts name ()-2-[4-chloro-2-fluoro-5-[(1-methyl-2-propynyl)
oxy]phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione CASRN[84478524]
DevelopmentcodesS-23121 (Sumitomo Chemical) SmilescodeCC(Oc1cc(N2C(=O)
C3=C(CCCC3)C2=O)c(F)cc1Cl)C#C
PHYSICAL CHEMISTRY: Mol. wt. 347.8 M.f. C18H15ClFNO3 Form White to light
brown crystals. M.p.115116.5C V.p. 0.28 mPa (20C) S.g./density 1.39
Solubility In water <1 mg/l (23C). In acetone 50%, ethyl acetate 3350%, xylene 2030%,
methanol 510%, hexane >1% (all 23C).
COMMERCIALISATION:
History Reported by T. Hamada etal. (Proc. Br. Crop Prot. Conf. Weeds 1989, 1, 41).
Herbicide introduced by Sumitomo Chemical Co. Ltd for control of broad-leaved weeds in
cereals.
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionSystemic herbicide
rapidly absorbed into plant tissues. Rapid necrosis or desiccation of stems and leaves is
induced in the presence of light and oxygen. Soil application induces shoot necrosis.
Uses Control of broad-leaved weeds including Galium aparine, Veronica spp.,and Viola,in
cereals. Formulation types SC. EC.
ANALYSIS:
Product by glc. Residues by hplc.
for rats >2000 mg/kg. Minimal eye irritation; not a skin irritant (rabbits). Other Non-
mutagenic in the Ames test.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp >1 mg/l.
flumipropyn 279
fluorbenside
Acaricide
NOMENCLATURE:
Common name fluorbenside (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname 4-chlorobenzyl 4-fluorophenyl sulfide
Chemical Abstracts name 1-chloro-4-[[(4-fluorophenyl)thio]methyl]
benzene CASRN[405301] DevelopmentcodesHRS 924; RD 2454
SmilescodeFc1ccc(SCc2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 252.7 M.f. C13H10ClFS Form Colourless crystals.
M.p.36C V.p. 10 mPa (20C) Solubility Practically insoluble in water.Very soluble in
acetone and aromatic hydrocarbons; soluble in saturated hydrocarbons. Stability Resistant
to hydrolysis but readily oxidised to the corresponding sulfoxide and sulfone.
COMMERCIALISATION:
History Acaricide reported by N. G. Clark etal. (J. Sci. Food Agric., 1957, 8, 566). Introduced
by The Boots Co., Ltd Agriculture (later Schering Agriculture). Patents GB 748604
APPLICATIONS:
ModeofactionNon-systemic acaricide. Uses Effective against adult mites, its high
volatility made it suitable for use in aerosols and in smokes. Formulation types Aerosols;
smokes.
PRODUCTS:
Discontinued products Fluorparacide* (Boots); Fluorsulphacide* (Boots).
ANALYSIS:
Residues determined by oxidation to the sulfone which is measured colorimetrically as a
derivative.
Oral Acute oral LD50 for ratsc.3000 mg/kg. NOEL In 2 y feeding trials, rats receiving
100 mg/kg diet suffered no ill effect, but in 21 d trials, those receiving 50 mg/kg daily
suffered slight liver and kidney enlargement.
fluoridamid
NOMENCLATURE:
Common name fluoridamide ((m) F-ISO); fluoridamid (BSI, E-ISO, ANSI)
IUPACname 3-(1,1,1-trifluoromethanesulfonamido)acet-p-toluidide
Chemical Abstracts name N-[4-methyl-3-[[(trifluoromethyl)sulfonyl]amino]
phenyl]acetamide CASRN[47000920] DevelopmentcodesMBR-6033
SmilescodeCC(=O)Nc1ccc(C)c(NS(=O)(=O)C(F)(F)F)c1
280 fluoridamid
PHYSICAL CHEMISTRY: Mol. wt. 296.3 M.f. C10H11F3N2O3S

COMMERCIALISATION:
History Plant growth regulator introduced by 3M Co.
PRODUCTS:
Discontinued products Sustar* (3M).
fluorodifen
Herbicide
NOMENCLATURE:
Common name fluorodifen (BSI, E-ISO, ANSI, WSSA, JMAF); fluorodif(ne) ((m) F-ISO)
IUPACname 4-nitrophenyl ,,-trifluoro-2-nitro-p-tolyl ether
Chemical Abstracts name 2-nitro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene
CASRN[15457053] DevelopmentcodesC 6989 (Ciba) Smilescode[O-][N+]
(=O)c1ccc(Oc2ccc(cc2[N+](=O)[O-])C(F)(F)F)cc1
PHYSICAL CHEMISTRY: Mol. wt. 328.2 M.f. C13H7F3N2O5 Form Yellowish crystals.
M.p.94.094.5C V.p. 0.0093 mPa (20C) Henry 1.53 103 Pa m3 mol1 (calc.)
dichloromethane 680, hexane 1.4, methanol 4.5, n-octanol 10, toluene 400 (all in g/l, 20C).
Stability No significant hydrolysis occured during 28 d at pH 19 (70C).
COMMERCIALISATION:
History Herbicide reported by L. Ebner etal. (Proc. Br.Weed Control Conf., 9th, 1968, 2,
1026). Introduced by Ciba AG (later Ciba-Geigy AG). Patents BE 628133; GB 1033163
APPLICATIONS:
ModeofactionContact herbicide. Uses A pre-em. and post-em. contact herbicide used
at 34 kg/ha. It was recommended pre-em. for use on drilled rice, but not for surface
seeded rice. Formulation types EC.
PRODUCTS:
Discontinued products Preforan* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD.
for rats >3000 mg/kg. Not irritant to skin; moderate irritant to eyes (rabbits).
Inhalation (6 h) for rats >0.99 mg/l air. NOEL (90 d) for rats 1000 mg/kg diet (67 mg/kg
daily), for dogs 316 mg/kg diet (10 mg/kg daily). Toxicity Class WHO (a.i.) U
fluorodifen 281
fluoromidine
Herbicide
NOMENCLATURE:
Common name fluoromidine (BSI (from 1984), E-ISO); fluromidine ((f) F-ISO, (before
1984) BSI)
IUPACname 6-chloro-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine
Chemical Abstracts name 6-chloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine
CASRN[13577714] DevelopmentcodesNC 4780
SmilescodeFC(F)(F)c1nc2ncc(Cl)cc2[nH]1
PHYSICAL CHEMISTRY: Mol. wt. 221.6 M.f. C7H3ClF3N3
COMMERCIALISATION:
History Herbicide evaluated by Fisons Ltd (later Schering Agriculture).
fluoronitrofen
Herbicide
F
Cl O NO2
Cl
NOMENCLATURE:
Common name fluoronitrofen (BSI, E-ISO); fluoronitrof(ne) ((m) F-ISO)
IUPACname 2,4-dichloro-6-fluorophenyl 4-nitrophenyl ether
Chemical Abstracts name 1,5-dichloro-3-fluoro-2-(4-nitrophenoxy)benzene
CASRN[13738631] DevelopmentcodesMo 500
Smilescode[O-][N+](=O)c1ccc(Oc2c(F)cc(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 302.1 M.f. C12H6Cl2FNO3
COMMERCIALISATION:
History Herbicide developed by Mitsui Toatsu Chemicals, Inc. (later Mitsui Chemicals, Inc.).
APPLICATIONS:
Biochemistry Inhibits protoporphyrinogen oxidase.
PRODUCTS:
Discontinued products Mo500* (Mitsui Toatsu).
282 fluoronitrofen
fluothiuron
Herbicide
NOMENCLATURE:
Common name fluothiuron (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(3-chloro-4-chlorodifluoromethylthiophenyl)-1,1-dimethylurea
Chemical Abstracts name N-[3-chloro-4-[(chlorodifluoromethyl)thio]phenyl]-
N,N-dimethylurea CASRN[33439451] DevelopmentcodesBAY KUE 2079A
SmilescodeCN(C)C(=O)Nc1ccc(SC(F)(F)Cl)c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 315.2 M.f. C10H10Cl2F2N2OS Form Colourless
crystals. M.p.113114C V.p. <17 mPa (20C) Henry <7.34 105 Pa m3 mol1 (calc.)
Solubility In water 73 g/l (20C). In cyclohexanone 377, dichloromethane 316 (both in
g/l, 20C).
COMMERCIALISATION:
History Herbicide introduced by Bayer AG. Patents GB 1314864; US 3931312
APPLICATIONS: Uses It was used at 2.5 g/ha to control dicotyledonous weeds in
paddy rice. Formulation types EC; GR .
PRODUCTS:
Discontinued products Clearcide* (Bayer).
percutaneous LD50 for rats >500 mg/kg. NOEL (90 d) for rats 40 mg/kg diet, for mice
20 mg/kg diet.
fluotrimazole
Fungicide
NOMENCLATURE:
Common name fluotrimazole (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(3-trifluoromethyltrityl)-1H-1,2,4-triazole
Chemical Abstracts name 1-[diphenyl[3-(trifluoromethyl)phenyl]methyl]-1H-
1,2,4-triazole CASRN[31251033] DevelopmentcodesBAY BUE 0620
SmilescodeFC(F)(F)c1cccc(c1)C(c2ccccc2)(c3ccccc3)n4cncn4
PHYSICAL CHEMISTRY: Mol. wt. 379.4 M.f. C22H16F3N3 Form Colourless crystalline
solid. M.p.132C Solubility In water 0.0015 mg/l (20C). In cyclohexanone 200,
dichloromethane 400, isopropanol 50, toluene 100 (all in g/kg, 20C). Stability Stable in
0.1M sodium hydroxide, but undergoesc.40% degradation in 0.2M sulfuric acid in 24 h.
COMMERCIALISATION:
History Fungicide reported by F. Grewe & K. H. Bchel (Mitt. Biol. Bundesanst. Land-
fluotrimazole 283
Forstwirtsch. Berlin-Dahlem, 1973, 151, 208). Introduced by Bayer AG.

Patents DE 1795249; US 3682950
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Uses A fungicide with specific action
against powdery mildew on barley, cucumbers, grapes, melons and peaches.
Formulation types EC; WP.
PRODUCTS:
Discontinued products Persulon* (Bayer).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by glc with FID (W. Specht,
Pflanz.-Nachr. Bayer (Engl. Ed.), 1977, 30, 55; W. Specht & M. Tillkes ibid., 1980, 33, 61).
rats >1000 mg/kg. NOEL (2 y) for rats 50 mg/kg diet; (90 d) for rats 800 mg/kg diet, for
dogs >5000 mg/kg diet. Toxicity Class WHO (a.i.) U
flupropacil
Herbicide
F3C O
N N CO2CH(CH3)2
CH3
O
Cl
NOMENCLATURE:
Common name flupropacil (BSI, E-ISO, (m) F-ISO)
IUPACname isopropyl 2-chloro-5-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-
trifluoromethylpyrimidin-1-yl)benzoate
Chemical Abstracts name 1-methylethyl 2-chloro-5-[3,6-dihydro-3-methyl-2,6-
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]benzoate CASRN[120890702]
DevelopmentcodesUCC-C4243 (Uniroyal)
PHYSICAL CHEMISTRY: Mol. wt. 390.7 M.f. C16H14ClF3N2O4
COMMERCIALISATION:
History Herbicide evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase. Uses Control of many broad-
leaved, and some annual grass weeds.
284 flupropacil
ENVIRONMENTAL FATE:
Soil/Environment Aerobic soil DT50 79 d; the major metabolite was the corresponding
acid; there was negligible mineralisation to CO2.
flupropadine; flupropadine hydrochloride

Rodenticide
CF3
C C CH2 N C(CH3)3
CF3
NOMENCLATURE:
Common name flupropadine (BSI, E-ISO, (f) F-ISO)
IUPACname 4-tert-butyl-1-[3-(,,,,,-hexafluoro-3,5-xylyl)prop-2-ynyl]piperidine
Chemical Abstracts name 1-[3-[3,5-bis(trifluoromethyl)phenyl]-2-
propynyl]-4-(1,1-dimethylethyl)piperidine CASRN[81613594] flupropadine
DevelopmentcodesM&B 36 892
PHYSICAL CHEMISTRY: Mol. wt. 391.4; (hydrochloride 427.9) M.f. C20H23F6N;
(hydrochloride C20H24ClF6N) Form The hydrochloride is a solid. M.p.201202C
(hydrochloride) Solubility In diethyl ether >150 g/l (5C).
COMMERCIALISATION:
History Rodenticide reported by A. P. Buckle (J. Hyg., 1985, 95, 505) and by F. P. Rowe etal.
(ibid., p. 513). Introduced by May & Baker Ltd (later Rhne-Poulenc Agriculture).
Patents EP 41324
APPLICATIONS: Uses Control of brown rats (Rattus norvegicus, including those
resistant to anticoagulant rodenticides) around grain stores. Also controls house mice
(Mus musculus). See W. Parnell, BCPC Monograph, 1987, No. 37, p. 125.
Oral Acute oral LD50 for mice 68 mg/kg.
flupropadine; flupropadine hydrochloride 285

flurazole
Herbicide safener
Cl S O
C
N
O CH2
CF3
NOMENCLATURE:
Common name flurazole (WSSA)
IUPACname benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate
Chemical Abstracts name phenylmethyl 2-chloro-4-(trifluoromethyl)-
5-thiazolecarboxylate CASRN[72850647] ECno2769423
DevelopmentcodesMON 4606 (Monsanto)
SmilescodeFC(F)(F)c1nc(Cl)sc1C(=O)OCc2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. is 98% pure. Mol. wt. 321.7 M.f. C12H7ClF3NO2S Form Colourless
crystals, with a slight sweet odour; (tech. is a yellow to tan solid). M.p.5153C
V.p. 3.9 10-2 mPa (25C) Henry 2.51 10-2 Pa m3 mol1 (calc.) S.g./density 0.96
(tech.) Solubility In water 0.5 mg/l (25C). Soluble in most organic solvents, including
alcohols, ketones, and xylene. Stability Stable below 93C. F.p. 392C (tech.) (Tag closed
cup)
COMMERCIALISATION:
History Herbicide safener introduced by Monsanto Co. in 1994.
Manufacturers Monsanto
APPLICATIONS:
55(11) 10431058). Uses Used as a herbicide safener. When applied as a seed protectant
to grain sorghum, acts as a safener against the phytotoxic effects of herbicides containing
alachlor or metolachlor. Formulation types Seed treatment; WG .
PRODUCTS:
Discontinued products Screen* (Monsanto).
ANALYSIS:
Details from Monsanto.
EU Status (1107/2009) Considered to be outside the scope of the Directive; considered
not to be a plant protection product.
286 flurazole
rabbits >5010 mg/kg. Non-irritating to skin; slightly irritating to eyes (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation No significant adverse health effects reported through
occupational exposure. NOEL (90 d) for dogs 300 mg/kg daily, for rats 5000 mg/kg diet.
ECClassification N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >2510 mg/kg. Dietary LC50 (5 d) for mallard
ducks and bobwhite quail >5620 ppm. Fish LC50 (96 h) for common carp 1.7, rainbow
trout 8.5, bluegill sunfish 11 mg/l. Daphnia LC50 (48 h) 6.3 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly degraded in soil, with the formation of water-soluble
metabolites. Breakdown is primarily microbial, with chemical breakdown of lesser
importance.
fluvalinate
IRAC3
NOMENCLATURE:
Common name fluvalinate (BSI, ANSI, E-ISO, (m) F-ISO)
IUPACname (RS)--cyano-3-phenoxybenzyl N-(2-chloro-,,-trifluoro-p-tolyl)-DL-
valinate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-
(trifluoromethyl)phenyl]-DL-valinate CASRN[69409945]
SmilescodeCC(C)C(Nc1ccc(cc1Cl)C(F)(F)F)C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY: Mol. wt. 502.9 M.f. C26H22ClF3N2O3 Form Tech. is a
viscous yellow oil. B.p. >450C (extrapolated) V.p. <0.013 mPa (25C) Kow logP >3.8
S.g./density 1.29 Solubility In water <0.005 mg/kg. Freely soluble in alcohols, aromatic
hydrocarbons, dichloromethane, diethyl ether. Stability DT50 30 d (pH 3 and pH 6), 12 h
(pH 9) (25C); 35 d (pH 3), 8 d (pH 6), 1 d (pH 9) (42C). Stable in glass >1.5 y (42C).
In sunlight thin films on glass or silica gel suffered 50% loss inc.2 d, an aqueous emulsion
(1.6 g/l) in glass in 12 d.
COMMERCIALISATION:
History Insecticide reported by C. A. Henrick etal. (Pestic. Sci., 1980, 11, 224) and by R. J.
Anderson (J. Agric. Food Chem., 1985, 33, 508). Fluvalinate introduced by Zoecon Corp. (later
Sandoz AG) and replaced by tau-fluvalinate (the D-valinate) [NOTE many references in the
literature have been made, in error, to fluvalinate rather than to tau-fluvalinate].
Patents US 4411912; US 4260633
fluvalinate 287
APPLICATIONS:
neurons by interaction with the sodium channel. ModeofactionContact insecticide
and acaricide. Uses A broad-range, foliar-applied insecticide and acaricide effective at
56168 g/ha against Aphididae, Cicadellidae, Lepidoptera, Thysanoptera, Tetranychidae and
Trialeurodes vaporariorum on ornamentals, vegetables, trees and vines.
PRODUCTS:
Other products Mavric (Nippon Soda); Discontinued products Kaiser* (Rocca);
Mavrik* (Zoecon).
ANALYSIS:
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Anal.
Profiles. By hplc (W. L. Fitch et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 79).
Residues determined by glc with ECD (idem, ibid.; AOACMethods, 18th Ed., 998.01; Resid.
Anal. Methods; Environ. Chem. Methods). See also Pestic. Anal. Man., II, 180.427, 186.3400.
for rats and rabbits >20000 mg/kg. Mild skin irritant; mild to moderate eye irritant.
NOEL (2 y) for rats 1 mg/kg b.w. daily (EPA IRIS). ADI/RfD (BfR) 0.005 mg/kg b.w. [1990];
(EPA) cRfD 0.01 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.) II
ENVIRONMENTAL FATE:
Soil/Environment In sandy loam under aerobic conditions DT50c.6 d.
FMC 1137
IRAC1B
NOMENCLATURE:
IUPACname bis(diethoxyphosphinothioyl) disulfide (i) +bis(diisopropoxyphosphinothio
yl) disulfide (ii) 75:25 mixture
Chemical Abstracts name bis(diethoxyphosphinothioyl) disulfide (i) +bis[di-(1-
methylethoxy)phosphinothioyl] disulfide (ii) CASRN[2901908] (i); [3031218] (ii)
DevelopmentcodesFMC 1137; NIA 1137
PHYSICAL CHEMISTRY: Mol. wt. 370.4 (i); 426.6 (ii) M.f. C8H20O4P2S4 (i);
C12H28O4P2S4 (ii)
COMMERCIALISATION:
History Insecticide and acaricide introduced by FMC Corp.
APPLICATIONS:
288 FMC 1137

PRODUCTS:
Discontinued products Phostex* (FMC).
FMC 19873
Herbicide
NOMENCLATURE:
IUPACname 6-tert-butyl-3-isopropyl[1,2]thiazolo[3,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisothiazolo[3,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isothiazolo[3,4-d]
pyrimidin-4(5H)-one CASRN[40915864] DevelopmentcodesFMC 19873
SmilescodeCC(C)c1snc2nc([nH]c(=O)c12)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 251.4 M.f. C12H17N3OS
COMMERCIALISATION:
History Herbicide evaluated by FMC Corp.
FMC 21844
Herbicide
NOMENCLATURE:
IUPACname 6-tert-butyl-3-isopropyl-1,2-oxazolo[5,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisoxazolo[5,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isoxazolo[5,4-d]
SmilescodeCC(C)c1noc2nc([nH]c(=O)c12)C(C)(C)C
COMMERCIALISATION:
FMC 21861
Herbicide
NOMENCLATURE:
IUPACname 6-tert-butyl-3-propyl-1,2-oxazolo[5,4-d]pyrimidin-4(5H)-one; 6-tert-butyl-
4,5-dihydro-3-propylisoxazolo[5,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-propylisoxazolo[5,4-d]
FMC 21861 289

SmilescodeCCCc1noc2nc([nH]c(=O)c12)C(C)(C)C
COMMERCIALISATION:
FMC 23486
Herbicide
NOMENCLATURE:
IUPACname 6-tert-butyl-3-isopropyl[1,2]oxazolo[3,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisoxazolo[3,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isoxazolo[3,4-d]
SmilescodeCC(C)c1onc2nc([nH]c(=O)c12)C(C)(C)C
COMMERCIALISATION:
History Herbicide reported by W. M. Dest etal. (Proc. Northeast.Weed Sci. Soc., 1973, 27,
31). Evaluated by FMC Corp.
FMC 25213
Herbicide
NOMENCLATURE:
IUPACname 2-ethyl-5-methyl-1,3-dioxan-5-yl 2-methylbenzyl ether; 2-ethyl-5-methyl-5-
(2-methylbenzyloxy)-1,3-dioxane
Chemical Abstracts name 2-ethyl-5-methyl-5-[(2-methylphenyl)methoxy]-1,3-
dioxane CASRN[41129106] cis- isomer DevelopmentcodesFMC 25213
SmilescodeCCC1OCC(C)(CO1)OCc2ccccc2C
COMMERCIALISATION:
History Herbicide reported (Ann. Meet. South. Weed Sci. Soc., 27th, 1974) and evaluated
by FMC Corp.
290 FMC 25213

fonofos
Insecticide
OCH2CH3
S
P
CH2CH3
S
IRAC1B
NOMENCLATURE:
Common name fonofos (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname O-ethyl S-phenyl (RS)-ethylphosphonodithioate
Chemical Abstracts name ()-O-ethyl S-phenyl ethylphosphonodithioate
CASRN[944229] unstated stereochemistry; [66767393] racemate; [62705719]
(R)- isomer; [62680039] (S)- isomer ECno2134080 DevelopmentcodesN-2790
(Stauffer) SmilescodeCCOP(=S)(CC)Sc1ccccc1
PHYSICAL CHEMISTRY:
Composition Tech. is 99.5%. The chiral forms have been isolated (R. Allahyari et al., J.
Agric. Food Chem., 1977, 25, 471; P. W. Lee et al., Pestic. Biochem. Physiol., 1978, 8, 146, 158).
Mol. wt. 246.3 M.f. C10H15OPS2 Form Clear, colourless liquid, with an aromatic odour.
B.p.c.130C /0.1 mmHg V.p. 28 mPa (25C) Kow logP = 3.94 S.g./density 1.16 (25C)
Solubility In water 13 mg/l (22C). Miscible with organic solvents, e.g. acetone, ethanol,
methyl isobutyl ketone, xylene, kerosene. Stability Stable below 100C. Hydrolysed in
acidic and alkaline media; DT50 101 d (pH 4), 74127 d (pH 7, depending on buffer), 1.8 d
(pH 10) (40C). In light DT50 12 d (pH 5, 25C). Specific rotation Optical rotations of the
chiral forms are reversed on solution in carbon tetrachloride, cyclohexane, methanol
F.p. 179C
COMMERCIALISATION:
History Insecticide reported by J. J. Menn & K. Szabo (J. Econ. Entomol., 1965, 58, 734).
Introduced by Stauffer Chemical Co. (later Zeneca Agrochemicals).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor; proinsecticide, activated by metabolic oxidative
desulfuration to the corresponding oxon. The (R)-isomer is more toxic to insects and mice
and a more potent inhibitor of cholinesterase than the (S)-isomer. ModeofactionSoil
insecticide with contact and stomach action. Uses Control of soil insects (especially
mole crickets, corn rootworms, symphylids, wireworms,Vine weevil larvae, cockchafer
larvae, cabbage root fly, onion fly, carrot fly, wheat bulb fly, etc.) in cereals, maize, sorghum,
vegetables, ornamentals, fruit (including citrus and bananas), vines, olives, potatoes, sugar
beet, sugar cane, peanuts, tobacco, and turf at 1.01.5 kg/ha. Formulation types GR; MG;
EC; SC. CS; Seed treatment.
fonofos 291
PRODUCTS:
Discontinued products Capfos* (Zeneca); Cudgel* (Zeneca); Dyfonate* (Zeneca);
Discontinuedmixtures Edge* (+pebulate) (Zeneca); Oslo* (+anthraquinone +oxine-
copper) (Sopra).
ANALYSIS:
Product analysis by capillary glc (J. E. Barney et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 269). Residues in crops, soil and water determined similarly (idem, ibid.; Environ.
Chem. Methods). See also Pestic. Anal. Man., I, 204; ibid., II, 180.221.
EHC 63 (1986) is a general review of organophosphorus insecticides. ICSC.708 (1997).
Oral Acute oral LD50 for male rats 11.5, female rats 5.5 mg/kg. Skin and eye Acute
percutaneous LD50 for rats 147, rabbits 32261, guinea pigs 278 mg/kg. Non-irritating to
skin and eyes (rabbits). Weak skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male
rats 51, female rats 17 g/l. NOEL (2 y) for rats 10 mg/kg diet (0.5 mg/kg b.w. daily);
for dogs 0.2 mg/kg b.w. daily. Not carcinogenic or teratogenic. ADI/RfD (EPA) cRfD
0.002 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.) Ia EPA (formulation) I or II
ECClassification T+; R27/28| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 128 mg/kg. Fish LC50 (96 h) for rainbow trout
0.05, bluegill sunfish 0.028 mg/l. Daphnia LC50 (48 h) 1 g/l. Bees Toxic to bees; LD50
0.0087 mg/bee.
ENVIRONMENTAL FATE:
Animals Metabolism in animals is similar to that in plants. Plants In plants, metabolism
involves oxidation to the phosphonothioate, and hydrolytic cleavage of the thiophenol
residue. Soil/Environment Under aerobic conditions, fonofos at 10 ppm was degraded
at a moderate rate, DT50 316 weeks in soils ranging from loamy sand to clay loam to peat;
adsorption K 15.3 (loam soil). The major degradate was O-ethyl ethanephosphonothioic
acid; other degradates included fonofos oxon, O-ethyl ethanephosphonic acid, O-ethyl
O-methylethyl phosphonate, diphenyl sulfide, methylphenyl sulfoxide and methylphenyl
sulfone.
292 fonofos
formothion
O
CH S
O CH P(OCH3)2
C S
NH
CH3
IRAC1B
NOMENCLATURE:
Common name formothion (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPACname S-[formyl(methyl)carbamoylmethyl] O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-formyl-N-methylacetamide
Chemical Abstracts name S-[2-(formylmethylamino)-2-oxoethyl] O,O-
dimethyl phosphorodithioate CASRN[2540821] ECno2198186
DevelopmentcodesJ-38; SAN 6913I SmilescodeCOP(=S)(OC)SCC(=O)N(C)C=O
PHYSICAL CHEMISTRY: Mol. wt. 257.3 M.f. C6H12NO4PS2 Form Odourless,
pale yellow, viscous liquid or crystalline mass. M.p.2526C B.p. Decomposes on
distillation. V.p. 0.113 mPa (20C) S.g./density 1.361 (20C) Solubility In water 2.6
g/l (24C). Completely miscible with common organic solvents, e.g. alcohols, ethers,
ketones, chloroform, benzene, toluene, xylene; slightly soluble in hexane; very slightly
soluble in ligroin and paraffin oil. Stability EC hydrolysed by water to dimethoate and
(dimethoxyphosphinothioylthio)acetic acid; DT50 1 d (pH 39, 23C). Hydrolysed more
rapidly in alkaline media. Dilute solutions in non-polar organic solvents are stable. The a.i. is
degraded inc.28 d at 54C.
COMMERCIALISATION:
History Insecticide reported by C. Klotzsche (Mitt. Geb. Lebensmittelunters. Hyg., 1961,
52, 341). Introduced by Sandoz AG (later Novartis Crop Protection AG).
Patents US 3176035; US 3178337 Manufacturers Novartis
APPLICATIONS:
acaricide with contact and stomach action. Uses Effective at 250500 g/ha against a
wide range of sucking and mining insects such as Aphididae, bugs, Cicadellidae, Coccidae,
Diaspididae, Drosophilidae, Margarodidae, Psyllidae, Tephritidae and Thysanoptera, as well
as against some chewing insects (Cydia pomonella and Epilachna spp.) and spider mites
on a variety of field crops, fruit trees, citrus and other tropical fruit, cotton, grapes, hops,
ornamentals, rice, sugar cane, tobacco and vegetables. Phytotoxicity Phytotoxic to some
varieties of peach, apricot and cherry. Formulation types EC; UL.
formothion 293
PRODUCTS:
Discontinued products Aflix* (Sandoz); Anthio* (Novartis);
Discontinuedmixtures Anthiomix* (+fenitrothion) (Novartis).
ANALYSIS:
Product analysis by glc with FID (CIPACHandbook, 1998, H, 178), or by glc with FPD
(AOACMethods, 18th Ed., 974.03). Residues determined by glc (A. Ambrus et al., J. Assoc. Off.
Anal. Chem., 1981, 64, 733; M. Wisson et al., Anal. Methods Pestic. Plant Growth Regul., 1976, 8,
123).
JMPR Evaln. I 72 (1994), 84 (1998). EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD50 for rats 365500, mice 190195, rabbits 570, cats 213 mg/kg.
Skin and eye Acute percutaneous LD50 for male rats >1000 mg/kg. Slightly irritating to
skin (rabbits). Inhalation LC50 (4 h) for rats 3.2 mg/l air (as Anthio 50ZP). NOEL In 2 y
feeding trials, rats and dogs receiving 80 mg/kg diet showed no adverse effects.
ADI/RfD (JMPR) ADI withdrawn [1996]. Water GV Excluded from GV derivation (U).
Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassification Xn; R21/22
ECOTOXICOLOGY:
Birds Acute oral LD50 for pigeons 630 mg/kg. Fish LC50 (72 h) for carp 10 mg/l; (96
h) for rainbow trout 38.3 mg/l. Daphnia LC50 (24 h) 16.1 mg/l. Algae EC50 (96 h) for
Scenedesmus subspicatus 42.3 mg/l. Bees Toxic to bees; LD50 (oral) 1.537, (topical) 1.789,
(contact, deposit) 28.447 g/g b.w. Worms LC50 (14 d) for earthworms 157.7 mg/kg soil.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, formothion is metabolised to
(dimethoxyphosphinthioylthio)acetic acid and polar metabolites, and elimination
occurs within 24 h. Plants In plants, formothion is metabolised to dimethoate (q.v.),
(dimethoxyphosphinthioylthio)acetic acid, bis(dimethylthiophosphoryl) disulfide, omethoate
(q.v.), and O,O-dimethyl hydrogen phosphorodithioate. Soil/Environment DT50 in loamy
soil <1 d, forming dimethoate (q.v.) and (dimethoxyphosphinthioylthio)acetic acid, which
ultimately dissipate.
formparanate
NOMENCLATURE:
Common name formparanate (BSI, E-ISO); formoparanate ((m) F-ISO)
IUPACname 4-dimethylaminomethyleneamino-m-tolyl methylcarbamate
294 formparanate
Chemical Abstracts name N,N-dimethyl-N-[2-methyl-4-[[(methylamino)carbonyl]oxy]

phenyl]methanimidamide CASRN[17702577] DevelopmentcodesUC 25 074
SmilescodeCNC(=O)Oc1ccc(N=CN(C)C)c(C)c1
COMMERCIALISATION:
History Insecticide and acaricide evaluated by Union Carbide.
APPLICATIONS:
fosmethilan
Insecticide
S
P(OCH3)2
O S
C CH2
CH3(CH2)2 N
Cl
IRAC1B
NOMENCLATURE:
Common name fosm(thilane) ((m) F-ISO); fosmethilan (BSI, E-ISO)
IUPACname S-[N-(2-chlorophenyl)butyramidomethyl] O,O-dimethyl phosphorodithioate;
2-chloro-N-(dimethoxyphosphinothioylthiomethyl)butyranilide
Chemical Abstracts name S-[[(2-chlorophenyl)(1-oxobutyl)amino]methyl] O,O-
dimethyl phosphorodithioate CASRN[83733828] DevelopmentcodesNE-79 168
SmilescodeCCCC(=O)N(CSP(=S)(OC)OC)c1ccccc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 367.8 M.f. C13H19ClNO3PS2 Form Colourless
crystals. M.p.42C V.p. 12 mPa Kow logP = 0.56 Solubility In water 2.3 mg/l (20C).
Stability On hydrolysis (20C) DT50 12.7 d (pH 4.5), 13.1 d (pH 7), 11.4 d (pH 8.3).
COMMERCIALISATION:
History Insecticide reported by K. Sagi etal. (Proc. 10th Int. Congr. Plant Prot., 1983, 1,
384).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Control of Diptera, Hemiptera,
Lepidoptera, Coleoptera, and Hymenoptera on pome fruit, stone fruit, vegetables, and field
crops. Formulation types EC.
PRODUCTS:
Discontinued products Nevifos* (Neviki); Neviphos* (Chemolimpex).
fosmethilan 295

Oral Acute oral LD50 for male rats 110 mg/kg, female rats 49 mg/kg. Skin and eye Acute
percutaneous LD50 for male rats >11000, female rats 6000 mg/kg. Slight skin and eye
irritant (rabbits). Inhalation LC50 for male rats >15 mg/l. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Birds Acute oral LD50 for pheasants 92, Japanese quail 6874 mg/kg. Dietary LC50 (8 d) for
pheasants 1330, quail 11250 mg/kg diet. Fish LC50 (96 h) for carp 6, goldfish 12 mg/l.
fospirate
Insecticide
IRAC1B
NOMENCLATURE:
Common name fospirate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname dimethyl 3,5,6-trichloro-2-pyridyl phosphate
Chemical Abstracts name dimethyl 3,4,5-trichloro-2-pyridinyl phosphate
CASRN[5598527] DevelopmentcodesDowco 217
SmilescodeCOP(=O)(OC)Oc1nc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 306.5 M.f. C7H7Cl3NO4P
COMMERCIALISATION:
History Insecticide introduced by Dow Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Torelle* (Dow).
fosthietan
IRAC1B
NOMENCLATURE:
Common name fosthietan (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname diethyl 1,3-dithietan-2-ylidenephosphoramidate (I)
Chemical Abstracts name (I); 2-(diethoxyphosphinylimino)-1,3-dithietane
CASRN[21548323] ECno2444377 DevelopmentcodesAC64 475
SmilescodeCCOP(=O)(OCC)N=C1SCS1
PHYSICAL CHEMISTRY: Mol. wt. 241.3 M.f. C6H12NO3PS2 Form Tech. is a yellow
296 fosthietan
liquid, with a mercaptan-like odour. V.p. 0.86 mPa (25C) Henry 4.15 106 Pa m3 mol1
(calc.) S.g./density 1.3 (25C) Solubility In water 50 g/l (25C). Soluble in acetone,
chloroform, methanol, toluene.
COMMERCIALISATION:
History Insecticide and nematicide described by W. K. Whitney & J. L. Aston (Proc. Br.
Insectic. Fungic. Conf. 8th, 1975, 2, 625). Introduced by American Cyanamid Co.
Patents US 3476837
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses A broad-range insecticide and nematicide,
effective with soil applications of 15 kg/ha. Formulation types GR; SL .
PRODUCTS:
Discontinued products Acconem* (Cyanamid); Geofos* (Cyanamid); Nematak*
(USA) (Cyanamid).
EHC 63 (1986; a general review of organophosphorus insecticides). EU Status
Oral Acute oral LD50 for rats 5.7 mg tech./kg. Skin and eye Acute percutaneous LD50
(24 h) for rabbits 54 mg/kg. Toxicity Class WHO (a.i.) O ECClassification T+; R27/28
ENVIRONMENTAL FATE:
Soil/Environment In soil DT50 (chemical degradation)c.1042 d.
frontalin
Insect pheromone
CH3
O
CH3
O
(-)-frontalin
See also The Manual of Biocontrol Agents entry: 4:403-4:405
An aggregation pheromone of the Western pine beetle (Dendroctonus brevicomis), the
spruce beetle (D. rufipennis), the Douglas fir beetle (D. pseuodtsugae), and the Southern
pine beetle (D. frontalis). For a general review, see G. Dupuis & N. Berland, http://www.
faidherbe.org/site/cours/dupuis/fronta4.htm.
NOMENCLATURE:
IUPACname 1,5-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane
Chemical Abstracts name 1,5-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane
frontalin 297
CASRN[28401390] (-)-frontalin, formerly [57917950], [22625043] and

[22625189]
PHYSICAL CHEMISTRY:
Composition The natural pheromone, (-)-frontalin, is the (1S,5R)- isomer (as drawn).
Mol. wt. 142.2 M.f. C8H14O2
COMMERCIALISATION:
Manufacturers ChemTica; Contech
APPLICATIONS: Uses In mixture with alpha-pinene, used for control of spruce
beetle (Dendroctonus rufipennis) and Douglas fir beetle (Dendroctonus pseudotsugae); also, in
mixture with exo-brevocomin and myrcene for control of Western pine beetle
(D. brevicomis). Lures are attached to host trees, which attract both male and female
beetles. The tree is then felled and destroyed before the insect brood emerges. This
reduces attacks in non-baited areas, and reduces the population of beetles.
furalaxyl
Fungicide
O O CO2CH3
C C
CH3
N
CH3 CH3
FRAC4, A1
NOMENCLATURE:
Common name furalaxyl (BSI, E-ISO, (m) F-ISO)
IUPACname methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate
Chemical Abstracts name methyl N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)-
DL-alaninate; N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)-DL-alanine methyl ester
CASRN[57646307] ECno2608751 DevelopmentcodesCGA 38 140 (Ciba-
Geigy) SmilescodeCOC(=O)C(C)N(C(=O)c1ccco1)c2c(C)cccc2C
PHYSICAL CHEMISTRY: Mol. wt. 301.3 M.f. C17H19NO4 Form White, odourless
crystals. M.p.70C and 84C (dimorphic) V.p. 0.07 mPa (20C) Kow logP = 2.7
Henry 9.3 105 Pa m3 mol1 (calc.) S.g./density 1.22 (20C) Solubility In water 230
mg/l (20C). In dichloromethane 600, acetone 520, methanol 500, benzene 480, hexane 4
(all in g/kg, 20C). Stability Relatively stable in neutral or weakly acidic media. Less stable
in alkaline media; on hydrolysis, DT50 (20C) (calc.) >200 d at pH 1 and pH 9, 22 d at
pH 10. Stable up to 300C.
298 furalaxyl
COMMERCIALISATION:
History Fungicide reported by F. J. Schwinn etal. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1977, 42, 1181). Introduced by Ciba-Geigy AG (later Syngenta AG) and first marketed in
1977. Patents BE 827419; GB 1448810
APPLICATIONS:
Biochemistry It is assumed that it inhibits protein synthesis in fungi, by interference
with the synthesis of ribosomal RNA. ModeofactionSystemic fungicide with protective
and curative action. Absorbed through the roots, stalk, and leaves, with translocation.
Uses Control of soil-borne diseases caused by Phytophthora and Pythium spp., and
other Oomycetes, on ornamentals. Formulation types GR; WP. Compatibility No
incompatibility known.
PRODUCTS:
Discontinued products Fonganil* (Ciba); Fongarid* (Syngenta).
ANALYSIS:
Product analysis by glc. Residues in plants and soils determined by glc with TID (D. J.
Caverley & J. Unwin, Analyst (London), 1980, 106, 389). Details available from Syngenta.
LD50 for rats >3100, rabbits 5508 mg/kg. Weak skin and eye irritant (rabbits). Non-
sensitising to skin (guinea pigs). NOEL (90 d) for rats 82 mg/kg daily; for dogs 1.8 mg/
kg b.w. daily. Other Not teratogenic, not mutagenic. Toxicity Class WHO (a.i.) III
ECClassification Xn; R22| R52, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 (8 d) for penguin ducks and Japanese quail >6000 mg/kg. LC50 (8 d)
for Japanese quail >6000 ppm. Fish LC50 (96 h) for rainbow trout 32.5, crucian carp 38.4,
guppies 8.7, catfish 60.0 mg/l. Daphnia LC50 (48 h) 39.0 mg/l. Algae EC50 for Scenedesmus
subspicatus 27 mg/l. Bees Not toxic to bees when used as directed; LD50 (24 h, oral) 5 to
>20 g/bee. Worms LC50 (14 d) for earthworms 510 mg/kg.
ENVIRONMENTAL FATE:
Animals After oral administration, furalaxyl is rapidly metabolised and eliminated via urine
and faeces. The metabolic pathways are independent of sex or dose level administered.
Residues in tissues were generally low, and there was no evidence for accumulation or
retention of furalaxyl or its metabolites. Plants Furalaxyl is metabolised to polar, water-
soluble, partially acidic, probably conjugated, degradation products. Soil/Environment In
soil, the compound dissipated with DT50 3165 d (2025C). Degradation is by cleavage of
the ester bond and by N-dealkylation.
furalaxyl 299
furcarbanil
Fungicide
NOMENCLATURE:
Common name furcarbanil (BSI, E-ISO, (m) F-ISO)
IUPACname 2,5-dimethyl-3-furanilide
Chemical Abstracts name 2,5-dimethyl-N-phenyl-3-furancarboxamide
CASRN[28562701] DevelopmentcodesBAS 319F (BASF)
COMMERCIALISATION:
History Fungicide evaluated by BASF AG.
furconazole
Fungicide
Cl OCH2CF3
O
Cl CH2
N
N
N
NOMENCLATURE:
Common name furconazole (BSI, E-ISO, (m) F-ISO)
IUPACname (2RS,5RS;2RS,5SR)-5-(2,4-dichlorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-
ylmethyl)-2-furyl 2,2,2-trifluoroethyl ether
Chemical Abstracts name 1-[[2-(2,4-dichlorophenyl)tetrahydro-5-(2,2,2-
trifluoroethoxy)-2-furanyl]methyl]-1H-1,2,4-triazole CASRN[112839335] unstated
stereochemistry DevelopmentcodesLS 840 608 (Rhne-Poulenc)
SmilescodeFC(F)(F)COC1CCC(O1)C(c2ccc(Cl)cc2Cl)n3cncn3
COMMERCIALISATION:
History Fungicide reported by Rhne-Poulenc Agrochimie.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. ModeofactionSystemic fungicide with
protective and curative action. Uses Control of fungal diseases of fruit and vines.
300 furconazole
furconazole-cis
Fungicide
Cl OCH2CF3
O
Cl CH2
N
N
N
NOMENCLATURE:
Common name furconazole-cis (BSI, E-ISO, (m) F-ISO)
IUPACname (2RS,5RS)-5-(2,4-dichlorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-
ylmethyl)-2-furyl 2,2,2-trifluoroethyl ether
Chemical Abstracts name cis-1-[[2-(2,4-dichlorophenyl)tetrahydro-5-(2,2,2-
trifluoroethoxy)-2-furanyl]methyl]-1H-1,2,4-triazole CASRN[112839324]
DevelopmentcodesLS 840 606 (Rhne-Poulenc)
SmilescodeFC(F)(F)COC1CCC(O1)C(c2ccc(Cl)cc2Cl)n3cncn3
PHYSICAL CHEMISTRY: Mol. wt. 396.2 M.f. C15H14Cl2F3N3O2 Form Colourless
crystals. M.p.86C V.p. 0.0145 mPa (25C) Solubility In water 21 mg/l. In organic
solvents 3701400 g/l.
COMMERCIALISATION:
History Fungicide reported by B. Zech etal. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 2,
503). Introduced by Rhne-Poulenc Agrochimie.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor ModeofactionSystemic fungicide with
protective and curative action. Uses For control of Ascomycetes, Basidiomycetes, and
Fungi Imperfecti (powdery mildew, rust, scab, leaf spot and other foliar pathogens) in fruit,
vines, cereals, and tropical crops. Formulation types EC; SC. WP.
for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Other Non-mutagenic in
micronucleus and Ames assays. Toxicity Class WHO (a.i.) II
furconazole-cis 301
furethrin
Insecticide
IRAC3
NOMENCLATURE:
IUPACname (RS)-3-furfuryl-2-methyl-4-oxocyclopent-2-enyl (1RS,2RS;1RS,2SR)-
2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; Roth: (RS)-3-furfuryl-
2-methyl-4-oxocyclopent-2-enyl (1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)
cyclopropanecarboxylate; 3-furfuryl-2-methyl-4-oxycyclopent-2-enyl ()-cis-trans-
chrysanthemate
Chemical Abstracts name ()-3-(2-furanylmethyl)-2-methyl-4-oxo-2-
cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other names furethrin CASRN[17080023], formerly [7076495]
SmilescodeCC(=CC1C(C(=O)OC/2CC(=O)/C(=C2/C)/Cc3ccco3)C1(C)C)C;without
stereochemistry:CC(=CC1C(C(=O)OC2CC(=O)C(=C2C)Cc3ccco3)C1(C)C)C
PHYSICAL CHEMISTRY: Mol. wt. 342.4 M.f. C21H26O4 Form Pale yellow liquid.
B.p. 187188C /0.4 mmHg Solubility Practically insoluble in water. Soluble in refined
kerosine.
COMMERCIALISATION:
History Insecticide (M. Matsui et al., J. Am. Chem. Soc., 1952, 74, 2181). The ester mixture
from the (RS)- alcohol and the (1R)-trans- acid is a more potent insecticide than the
complete mixture of stereoisomers (W. A. Gersdorff & N. Mitlin, J. Econ. Entomol., 1952, 45,
849).
APPLICATIONS:
neurons by interaction with the sodium channel. ModeofactionContact insecticide.
Uses An insecticide giving a rapid knockdown of Musca domestica.
furmecyclox
Fungicide
NOMENCLATURE:
Common name furm(cyclox) ((m) F-ISO); furmecyclox (BSI, E-ISO)
IUPACname methyl N-cyclohexyl-2,5-dimethyl-3-furohydroxamate; methyl N-cyclohexyl-
2,5-dimethylfuran-3-carbohydroxamate
Chemical Abstracts name N-cyclohexyl-N-methoxy-2,5-dimethyl-3-furancarboxamide
CASRN[60568050] ECno2623020 DevelopmentcodesBAS 389F (BASF)
SmilescodeCON(C1CCCCC1)C(=O)c2cc(C)oc2C
PHYSICAL CHEMISTRY: Mol. wt. 251.3 M.f. C14H21NO3 Form Crystalline solid.
M.p.33C V.p. 8.4 mPa (20C) Henry 7.04 103 Pa m3 mol1 (calc.) Solubility In
302 furmecyclox
water 0.3 g/l (20C). In acetone, chloroform, ethanol >1 kg/kg. Stability Decomposed by
sunlight and hydrolysed under strongly acidic and strongly alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer & B. Zeeh (Pestic. Sci., 1977, 8, 320).
Introduced by BASF AG. Patents DE 2455082; GB 1517960; US 3993772
APPLICATIONS: Uses Used as a seed treatment for cereals, cotton (against Rhizoctonia
solani), potatoes and other crops. Also to protect wood against fungal decay.
Formulation types DS; Wet treatment.
PRODUCTS:
Discontinued products Campogran* (BASF); Epic* (Gustafson); XyligenB* (BASF).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FID.
>5000 mg/kg. Potential skin irritant.. Toxicity Class WHO (a.i.) U
ECClassification R40| N; R50, R53
furophanate
Fungicide
NOMENCLATURE:
Common name furophanate (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname methyl 4-(2-furfurylideneaminophenyl)-3-thioallophanate
Chemical Abstracts name methyl [[[2-[(2-furanylmethylene)amino]phenyl]amino]
thioxomethyl]carbamate CASRN[53878174] DevelopmentcodesRH-3928
SmilescodeCOC(=O)NC(=S)Nc1ccccc1N=Cc2ccco2
COMMERCIALISATION:
furophanate 303
furyloxyfen
Herbicide
O
O
CF3 O NO2
Cl
NOMENCLATURE:
Common name furyloxyf(ne) ((m) F-ISO); furyloxyfen (BSI, E-ISO)
IUPACname ()-5-(2-chloro-,,-trifluoro-p-tolyloxy)-2-nitrophenyl tetrahydro-3-furyl
ether
Chemical Abstracts name ()-3-[5-[2-chloro-4-(trifluoromethoxy)phenoxy]-2-
nitrophenoxy]tetrahydrofuran CASRN[80020413] unstated stereochemistry
DevelopmentcodesMT-124 (Mitsui Toatsu)
Smilescode[O-][N+](=O)c1ccc(Oc2ccc(c(Cl)c2)C(F)(F)F)cc1OC3CCOC3
PHYSICAL CHEMISTRY: Mol. wt. 403.7 M.f. C17H13ClF3NO5
COMMERCIALISATION:
History Herbicide developed by Mitsui Toatsu Chemicals, Inc.
APPLICATIONS:
Biochemistry Protoporphyrinogen inhibitor.
gliotoxin
Fungicide
NOMENCLATURE:
Common name gliotoxin ()
IUPACname (3R,5aS,6S,10aR)-2,3,5a,6,10,10-hexahydro-6-hydroxy-3-hydroxymethyl-2-
methyl-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Chemical Abstracts name [3R-(3,5a,6,10a)]-2,3,5a,6-tetrahydro-6-hydroxy-
3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
CASRN[67992] SmilescodeCN1C(=O)C23CC4=CC=CC(O)C4N3C(=O)
C1(CO)SS2
PHYSICAL CHEMISTRY: Mol. wt. 326.4 M.f. C13H14N2O4S2 M.p.221C (decomp.)
Solubility In water 700 mg/l (30C). Moderately soluble in acetic acid, acetone,
chloroform, ethanol, methanol. Stability Easily oxidised and is inactivated in 10 min at
100C; it is fairly stable in aqueous acids, but is rapidly inactivated in neutral or alkaline
solutions. Specific rotation []25D 290 (800 mg/l ethanol)
304 gliotoxin
COMMERCIALISATION:
Production Formed in cultures of Trichoderma viride, Gliocladium fimbriatum, Aspergillus
fumigatum and several Penicillium spp. History Antifungal antibiotic isolated by R. Weindling
& O. H. Emerson (Phytopathology, 1936, 26, 1068) and structure established by M. R. Bell (J.
Am. Chem. Soc., 1958, 80, 1001). Instability has limited its use in crop protection.
APPLICATIONS:
Biochemistry Antifungal antibiotic. Uses It is antifungal, at 4 mg/l inhibiting spore growth
of Botrytis allii and at 2 mg/l those of Fusarium coeruleum.
Other An intravenous injection of 45 mg/kg was lethal to rabbits (J. R. Johnson et al., ibid.,
1943, 65, 2005).
glyodin
NOMENCLATURE:
Common name glyodin (BSI, E-ISO, (m) F-ISO)
IUPACname 2-heptadecyl-2-imidazoline acetate; acetic acid - 2-heptadecyl-2-imidazoline
(1:1)
Chemical Abstracts name 2-heptadecyl-4,5-dihydro-1H-imidazolyl monoacetate
CASRN[556229] DevelopmentcodesCrag Fruit Fungicide 341
SmilescodeCCCCCCCCCCCCCCCCCC1=NCC[NH2+]1.CC(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 368.6 M.f. C22H44N2O2 Form Light orange
crystals. M.p.6268C S.g./density 1.035 (20C) Solubility Practically insoluble in
water. In isopropanolc.390 g/kg; practically insoluble in acetone, toluene. Stability Readily
hydrolysed by alkali to N-(2-aminoethyl)heptadecanamide.
COMMERCIALISATION:
History Fungicide reported by R. H. Wellman & S. E. A. McCallan (Contrib. Boyce
Thompson Inst., 1946, 14, 151). Introduced by Union Carbide Corp. Patents GB 598927;
US 2540170; US 2540171
APPLICATIONS:
ModeofactionProtective fungicide and acaricide. Uses Sprays, after addition of
calcium carbonate to give the free base, were used to protect foliage from attack by fungi.
Formulation types SL . Compatibility Incompatible with oils or EC formulations.
PRODUCTS:
Discontinued products CragFungicide 341* (Union Carbide).
ANALYSIS:
Residues determined by spectrometry (AOACMethods 18th Ed., 963.23) or by titration
with an anionic surfactant (E. F. Hillenbrand et al., Anal. Chem., 1951, 23, 626).
glyodin 305
NOEL In feeding trials, dogs tolerated 71 mg a.i. (as formulation)/kg diet; guinea-pigs
tolerated 153 mg/kg diet; rats tolerated 91 mg/kg diet (C. P. Carpenter, Arch. Ind. Hyg.
Occup. Med., 1951, 4, 494). Toxicity Class WHO (a.i.) O
glyphosate-trimesium
Herbicide
HRACG WSSA 9
The trimethylsulfonium salt of glyphosate.
NOMENCLATURE:
IUPACname trimethylsulfonium N-(phosphonomethyl)glycinate
Chemical Abstracts name N-(phosphonomethyl)glycine trimethylsulfonium salt
Other names sulfosate CASRN[81591813] DevelopmentcodesSC.224;
ICIA0224 (ICI)
PHYSICAL CHEMISTRY: Mol. wt. 245.2 M.f. C6H16NO5PS Form White solid.
M.p.Decomp. 150C V.p. <0.01 mPa (20C) Kow logP = 2.9 Henry <2 10-9 Pa m3
mol1 (calc.) S.g./density 1.42 Solubility In water >1000 g/l. In acetone, chlorobenzene,
ethanol, kerosene, xylene <5 (all in g tech./l).
COMMERCIALISATION:
History This discontinued salt of glyphosate introduced in Spain (1989) by ICI
Agrochemicals (later Syngenta AG).
PRODUCTS:
Discontinued products Coloso* (Syngenta); Ouragan* (Syngenta); Touchdown*
(Syngenta); Toupan* (Syngenta); Zapp* (Syngenta); Discontinuedmixtures Allzett*
(+diquat dibromide) (Otsuka).
ANALYSIS:
Residues by gc/FPD (Resid. Anal. Methods), or gc/ms (ibid.); see also Pestic. Anal. Man., II,
180.489. In soil, by gc/NPD (Environ. Chem. Methods). In water, by hplc/FLD (ibid.).
Oral Acute oral LD50 for male rats 748, female rats 755, mice 1250 mg/kg. Skin and eye
Acute percutaneous LD50 for rabbits >2000 mg/kg. Inhalation LC50 (4 h) for rats 6.2 mg/l
air. NOEL (2 y) for rats 21 mg/kg b.w. No teratogenic effect observed. ADI/RfD (EC)
0.2 mg/kg b.w. [2001]; (EPA) 0.1 mg/kg b.w. [1994]. ECClassification Xn; R22| N; R51,
R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >2050, mallard ducks 950 mg tech./kg. Fish LC50
(96 h) for trout 1800, bluegill sunfish >3500 mg/l. Daphnia LC50 (48 h) 12 mg/l. Algae
EC50 19 mg/l. Bees LD50 (oral) >0.4 mg/bee; (contact) 0.39 mg/bee. Worms LD50 (14 d)
306 glyphosate-trimesium
>1000 mg/kg soil. Other beneficial Harmless under field conditions at field application
rates to parasitic wasps (Aphidius rhopalosiphi), lycosid spiders and carabid beetles
(Pterostichus melanarius) (IOBC).
glyphosine
NOMENCLATURE:
Common name glyphosine (BSI, E-ISO, (f) F-ISO, ANSI)
IUPACname N,N-bis(phosphonomethyl)glycine (I)
DevelopmentcodesCP 41 845 (Monsanto)
SmilescodeOC(=O)CN(CP(=O)(O)O)CP(=O)(O)O
PHYSICAL CHEMISTRY: Mol. wt. 263.1 M.f. C4H11NO8P2 Form Colourless solid.
M.p.200C (decomp.) V.p. <1.33 104 mPa (100C) S.g./density 1.8 Solubility In
water 350 g/l (20C). Insoluble in benzene; very slightly soluble in ethanol. Stability Stable
to light. F.p. Non-flammable
COMMERCIALISATION:
History Increase in carbohydrate deposition in sugar cane described by C. A. Porter & L.
E. Ahlrichs (Hawaii Sugar Tech. Rep. 1971, 1972, 30, 71). Plant growth regulator introduced
by Monsanto Co. Patents US 3556762 Manufacturers CCA Biochemical
APPLICATIONS:
ModeofactionAbsorbed by foliage and translocated throughout the plant especially to
growing points. Uses A plant growth regulator used to hasten ripening of sugar cane and
to increase the sucrose content. Effective rates are 2.44.5 kg/ha. It was removed from the
juice during processing. Formulation types SP.
PRODUCTS:
Discontinued products Polaris* (Monsanto).
ANALYSIS:
Residues determined by glc of a derivative by FPD.
Oral Acute oral LD50 for rats 7200 mg tech./kg. Skin and eye Non-irritant to skin and
corrosive to eyes (rabbits). NOEL In 2 y feeding trials, no adverse effect was observed at
rates up to 300 mg/kg diet in dogs, or 10000 mg/kg diet in rats, and reproduction was not
affected. In 1.5 y trials, mice receiving 10000 mg/kg diet showed no effect and no significant
tumour frequency. Toxicity Class WHO (a.i.) U ECClassification Xi; R41
ENVIRONMENTAL FATE:
Soil/Environment Inactivated by microbial action in soils, DT50c.60 d.
glyphosine 307
griseofulvin
Fungicide
NOMENCLATURE:
Common name griseofulvin (BSI, E-ISO, BAN, JMAF); gris(ofulvine) ((f) F-ISO)
IUPACname (2S,6R)-7-chloro-2,4,6-trimethoxy-6-methylspiro[benzofuran-2(3H),1-
cyclohex-2-ene]-3,4-dione; 7-chloro-2,4,6-trimethoxybenzofuran-2(3H)-spiro-1-
cyclohex-2-ene-3,4-dione
Chemical Abstracts name (1S)-trans-7-chloro-2,4,6-trimethoxy-6-
methylspiro[benzofuran-2(3H),1-[2]cyclohexene]-3,4-dione Other names "curling
factor" CASRN[126078] SmilescodeCOC1=CC(=O)CC(C)C21Oc3c(C2=O)
c(OC)cc(OC)c3Cl
PHYSICAL CHEMISTRY: Mol. wt. 352.8 M.f. C17H17ClO6 Form Colourless crystals.
M.p.222C (subliming from 210C) Solubility Practically insoluble in water. In DMSO
120140 g/l; low solubility in most organic solvents; practically insoluble in petroleum oils.
Stability Stable between pH 3.0 and pH 8.8. Specific rotation [] +312 (acetone)
COMMERCIALISATION:
Production Isolated from cultures of Penicillium griseofulvum. History Antifungal
antibiotic isolated by A. E. Oxford etal. (Biochem. J., 1939, 33, 240), structure elucidated by
J. F. Grove etal. (Chem. Ind. (London), 1955, p. 160; J. Chem. Soc., 1956, p. 3949; Q. Rev. Chem.
Soc., 1963, 17, 1). Introduced by Glaxo Ltd, now restricted to veterinary and anthelmintic
uses.
APPLICATIONS:
Biochemistry Antifungal antibiotic. ModeofactionA fungicide affecting the
morphogenesis of chitinous cell walls (P. W. Brian Ann. Bot. (London), 1949, 13, 59) with
some systemic activity (idem, Nature (London), 1951, 167, 347; S. H. Crowdy & D. Pramer,
Chem. Ind. (London), 1955, p. 160). Formulation types DP; EC; WP.
ANALYSIS:
Product analysis by uv spectrometry (G. C. Ashton & A. P. Brown, Analyst (London), 1956, 81,
220). Residues determined by bioassay (P. W. Brian, Trans. Br. Mycol. Soc., 1946, 29, 173).
IARC 79 (2001).
IARC Class 2B
308 griseofulvin
halacrinate
Fungicide
NOMENCLATURE:
Common name halacrinate (BSI, E-ISO, (m) F-ISO)
IUPACname 7-bromo-5-chloro-8-quinolyl acrylate
Chemical Abstracts name 7-bromo-5-chloro-8-quinolinyl 2-propenoate
SmilescodeClc1cc(Br)c(OC(=O)C=C)c2ncccc12
PHYSICAL CHEMISTRY: Mol. wt. 312.6 M.f. C12H7BrClNO2 Form Colourless
crystals. M.p.100101C V.p. 0.08 mPa (20C) Henry 4.17 103 Pa m3 mol1 (calc.)
Solubility In water 6 mg/l (20C). In benzene 370, dichloromethane 610, methanol 27
(all in g/l, 20C). Stability Relatively stable in neutral or slightly acid media but is slowly
hydrolysed by alkali.
COMMERCIALISATION:
History Fungicide reported by J. M. Smith etal. (Proc. Br. Insectic. Fungic. Conf., 8th, 1975, 2,
421). Evaluated by Ciba-Geigy AG. Patents CH 528214; GB 1324296
APPLICATIONS:
ModeofactionProtective and curative fungicide. Uses It was used, in mixture with
captafol, to control Erysiphe graminis and Septoria spp. at 0.50.75 kg/ha.
PRODUCTS:
Discontinuedmixtures Tilt* (+captafol) (Ciba-Geigy).
rats >3170 mg/kg. Toxicity Class WHO (a.i.) O
halosafen
Herbicide
HRACE WSSA 14; diphenyl ether
NOMENCLATURE:
Common name halosafen (BSI, ANSI, E-ISO); halosaf(ne) ((m) F-ISO)
IUPACname 5-(2-chloro-,,,6-tetrafluoro-p-tolyloxy)-N-ethylsulfonyl-2-
nitrobenzamide
Chemical Abstracts name 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-N-
(ethylsulfonyl)-2-nitrobenzamide CASRN[77227691] SmilescodeCCS(=O)(=O)
NC(=O)c1cc(Oc2c(F)cc(cc2Cl)C(F)(F)F)ccc1[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 470.8 M.f. C16H11ClF4N2O6S
halosafen 309
COMMERCIALISATION:
History Herbicide evaluated by ICI Agrochemicals.
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor.
haloxydine
Herbicide
NOMENCLATURE:
Common name haloxydine (BSI, E-ISO, (f) F-ISO)
IUPACname 3,5-dichloro-2,6-difluoropyridin-4-ol
Chemical Abstracts name 3,5-dichloro-2,6-difluoro-4-pyridinol CASRN[2693610]
DevelopmentcodesPP493 SmilescodeOc1c(Cl)c(F)nc(F)c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 200.0 M.f. C5HCl2F2NO
COMMERCIALISATION:
History Herbicide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
HC-252
Herbicide
CO2CH2CH3
CH3
O C H
Cl C O
F3C O Cl
NOMENCLATURE:
IUPACname ethyl O-[2-chloro-5-(2-chloro-,,-trifluoro-p-tolyloxy)benzoyl]-L-lactate
Other names ethoxyfen-ethyl (non-approved name) CASRN[131086425]
DevelopmentcodesHC-252 (Budapest Chemical) SmilescodeCCOC(=O)[C@@H]
(C)OC(=O)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1Cl;without stereochemistry:CCOC(=O)
C(C)OC(=O)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 451.2 M.f. C19H15Cl2F3O5 (for ethyl ester)
Form Brown, oily, viscous liquid (tech.). Solubility Very soluble in acetone, methanol and
xylene.
310 HC-252
COMMERCIALISATION:
History Herbicide reported by J. Bakos etal. (Proc. Br. Crop Prot. Conf. Weeds, 1991, 1, 83).
Manufacturers Budapest Chemical
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor; acts by tetrapyrrole and
protoporphyrin accumulation. Tetrapyrroles are photosensitisers which cause photo-
oxidation, leading to leaf necrosis and plant death. ModeofactionContact herbicide.
Uses Control of broad-leaved weeds in winter wheat, winter barley, peas, soya beans and
peanuts. Formulation types EC.
1113 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000, rabbits >2000 mg/kg.
Non-irritating to skin; moderate eye irritant (rabbits). Inhalation LC50 (14 d) for male rats
9679, female rats 9344 mg/m3 air. Other Non-mutagenic in Salmonella micronucleus test,
in vitro chromosome aberration test, and in vitro mouse medulla micronucleus test.
ENVIRONMENTAL FATE:
Soil/Environment Since HC-252 is a contact herbicide, there is no soil residual effect,
and no soil persistence problems for following crops.
heptachlor
Insecticide
Cl Cl
Cl
Cl
Cl
Cl
Cl
IRAC2A
NOMENCLATURE:
Common name heptachlor (BSI, E-ISO, ESA, JMAF); heptachlore ((m) F-ISO)
IUPACname 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene
Chemical Abstracts name 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methano-
1H-indene CASRN[76448] ECno2009623; 2138310 heptachlor epoxide
DevelopmentcodesE 3314;Velsicol 104 SmilescodeClC1C=CC2C1C3(Cl)C(=C(Cl)
C2(Cl)C3(Cl)Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade isc.72% heptachlor and 28% related compounds.
Mol. wt. 373.3 M.f. C10H5Cl7 Form Crystalline solid; (tech., waxy solid). M.p.9596C;
(tech. 5560C) B.p. 135145C V.p. 53 mPa (25C, pure)
heptachlor 311
Kow logP = 4.45.5 (Agchem. Desk Ref.) Henry 3.53 102 Pa m3 mol1 (calc.)
S.g./density 1.58 (20C) (tech.) Solubility In water 0.056 mg/l (2529C). Soluble
in many organic solvents, e.g. in acetone 75, benzene 106, xylene 102, cyclohexanone
119, carbon tetrachloride 113, ethanol 4.5 (all in g/100 ml). Tech. in cyclohexanone
1.65 kg/l, ethanol 62.5 g/l, deodorised kerosene 263 g/l, xylene 1.41 kg/l (2030C).
Stability Stable in daylight, air, moisture, and moderate heat (up to 160C). Not readily
dehydrochlorinated, but is susceptible to epoxidation. Hydrolysis DT50 4.3 d (pH 5), 4.5 d
(pH 6, 7), 3.0 d (pH 8) (all 25C) (cited in Agchem. Desk Ref.).
COMMERCIALISATION:
History It was isolated from tech. chlordane, and its insecticidal properties reported by W.
M. Rogoff & R. L. Metcalf (J. Econ. Entomol., 1951, 44, 910). Introduced by Velsicol Chemical
Corp. Patents US 3437664
APPLICATIONS:
ModeofactionNon-systemic insecticide with contact, stomach, and some respiratory
action. Uses Control of termites, ants, and soil insects in cultivated and uncultivated soils.
Applied as a seed treatment, soil treatment, or directly to foliage. Also used for control of
household insects. Formulation types DP; EC; GR; WP; Seed treatment.
PRODUCTS:
Discontinued products Drinox* (Velsicol).
ANALYSIS:
Product analysis by glc with FID (AOACMethods, 18th Ed., 968.04) or by determination of
a labile chlorine substituent (ibid., 962.07; CIPACHandbook, 1970, 1, 420; FAO Specification
(CP/47); Organochlorine Insecticides, 1973). Residues determined by glc, tlc or paper
chromatography (AOACMethods, 18th Ed., 970.52; A. Ambrus et al., J. Assoc. Off. Anal. Chem.,
1981, 64, 773; Analyst (London), 1979, 104, 425; H. K. Suzuki et al., Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 73; Man. Pestic. Residue Anal., pp. 5, 6, 810, 12, 19; Anal. Methods
Residues Pestic., 1988, Part I, M1, M12). In drinking water by glc with ECD (AOACMethods,
18th Ed., 990.06). See also Pestic. Anal. Man., I, 104, 204, 208, 302, 303, 504.
EHC 38 (1984). JMPR Mtg. 71 (1994); JMPR Evaln. I 69 (1993), 72 (1994); JMPR Evaln. II 64
(1991). HSG 14 (1988). PDS 19 (1975). ICSC.743 (2003). CICAD 70 (2006). IARC 79 (2001).
banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 2B
Oral Acute oral LD50 for rats 147220, guinea pigs 116, mice 68 mg/kg.
Skin and eye Acute percutaneous LD50 for rabbits 2002000, rats 119250 mg/kg.
Irritating to eyes; not a skin irritant (rabbits). Inhalation LC50 (4 h) for rats 2.0200 mg/l
air (aerosol). NOEL The target organ is the liver, with NOEL in rats 5 mg/kg diet, and
312 heptachlor
in dogs 0.51.0 mg/kg diet. A 3-generation feeding study gave NOEL in rats 7 mg/kg diet,
and in dogs (2-generation reproduction study) 1 mg/kg diet. Heptachlor epoxide is not
teratogenic in rabbits at 5 mg/kg daily. ADI/RfD (JMPR) 0.0001 mg/kg b.w. (PTDI) [1994];
(EPA) cRfD 0.0005 mg/kg b.w. [1992]. Water GV GV not established (O). Other Animal
experiments have indicated that heptachlor is carcinogenic in some mice and rat strains,
perhaps acting as a promoter, rather than an initiator, of carcinogenesis (S. S. Epstein, Sci.
Total Environ., 1976, 6, 103154). A committee of the United States National Academy
of Sciences ruled that heptachlor is a carcinogen to certain mouse strains. In vitro and
in vivo experiments showed that heptachlor is non-mutagenic, and there was also no
evidence of teratogenicity in rabbits. Toxicity Class WHO (a.i.) II EPA (formulation) II
ECClassification T; R24/25| R40| R33| N; R50, R53: (heptachlor epoxide T; R25| R40|
R33| N; R50, R53) PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducklings >2000 mg/kg. Dietary LC50 (8 d) for bobwhite
quail 450700, Japanese quail 8095, pheasants 250275 mg/kg diet. Fish LC50 (96 h) for
rainbow trout 7, bluegill sunfish 26, fathead minnows 78130 ;g/l.
ENVIRONMENTAL FATE:
Animals The principal metabolites in animals are heptachlor epoxide (found in the tissues,
faeces, and urine), and 1-exo-hydroxychlordene epoxide, a hydrophilic metabolite excreted
in the urine. There is a strong tendency for the epoxide to accumulate in body fat.
Plants In plants, heptachlor epoxide is a metabolite. Soil/Environment In water,
heptachlor rapidly undergoes hydrolysis to 1-hydroxychlordene, which then undergoes
microbial epoxidation to 1-hydroxy-2,3-epoxychlordene. Similar degradation pathways
occur in moist soil. Soil DT50 910 months when used at agricultural rates.
2-(2-heptadecyl-2-imidazolin-1-yl)ethanol
Fungicide
NOMENCLATURE:
IUPACname 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol
Chemical Abstracts name 2-heptadecyl-4,5-dihydro-1H-imidazole-
1-ethanol CASRN[95192] DevelopmentcodesFungicide 337
SmilescodeCCCCCCCCCCCCCCCCCC1=NCCN1CCO
COMMERCIALISATION:
History Fungicide evaluated by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
2-(2-heptadecyl-2-imidazolin-1-yl)ethanol 313
heptafluthrin
Insecticide
H O F
H F
O
CF3
H3 C CH3 F
F O
NOMENCLATURE: CH3
Common name heptafluthrin (pa ISO)
IUPACname 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (1RS,3RS;1RS,3SR)-2,2-
dimethyl-3-[(1Z)-3,3,3-trifluoroprop-1-enyl]cyclopropanecarboxylate
Chemical Abstracts name [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]
methyl 2,2-dimethyl-3-[(1Z)-3,3,3-trifluoro-1-propen-1-yl]cyclopropanecarboxylate
CASRN[1130296659]
SmilescodeFC1=C(F)C(COC)=C(F)C(F)=C1COC(C2C(/C([H])=C([H])\C(F)(F)F)
C2(C)C)=O
PHYSICAL CHEMISTRY: Mol. wt. 414.3 M.f. C18H17F7O3
heptenophos
Insecticide
O
P(OCH3)2
O
Cl
IRAC1B; organophosphate
NOMENCLATURE:
Common name heptenophos (BSI, E-ISO, (m) F-ISO)
IUPACname 7-chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl dimethyl phosphate
Chemical Abstracts name 7-chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl dimethyl
phosphate CASRN[23560590] ECno2457370 DevelopmentcodesHoe 02982
(Hoechst); AE F002982 (AgrEvo) Official codes OMS 1845
Smilescodewithout stereochemistry: COP(=O)(OC)OC1=C(Cl)C2C=CCC21
PHYSICAL CHEMISTRY:
Composition Tech. grade is 93% pure. Mol. wt. 250.6 M.f. C9H12ClO4P Form Light
brown liquid, with odour typical of a phosphate ester. B.p. 64C /0.075 mmHg V.p. 65
mPa (15C); 170 mPa (25C) Kow logP = 2.32 (OECD 117) Henry 5.73 105 (20C);
314 heptenophos
2.33 104 (25C) (both in Pa m3 mol1) S.g./density 1.28 (20C) Solubility In water
2.2 g tech./l (20C). Readily miscible with most organic solvents, e.g. in acetone, methanol,
xylene >1, hexane 0.13 (all in kg/l, 25C). Stability Hydrolysed in acidic and alkaline
media. F.p. 165C (Cleveland, open); 152C (Pensky-Martens, closed)
COMMERCIALISATION:
History First described under an erroneous structure (CASRN[34783409], Biul.
Inst. Ochr. Rosl., 1971, No. 50, p. 109); insecticidal and acaricidal properties against crop
pests reported by R. T. Hewson (Proc. Br. Insectic. Fungic. Conf., 8th, 1975, 2, 697) and against
veterinary pests by W. Bonin (ibid., p. 705). Introduced by Hoechst AG. Patents DE
1643608; GB 1194603; US 3600474; US 3705240; US 3810919 (to Ciba-Geigy)
APPLICATIONS:
contact, stomach and respiratory action. Readily penetrates the plant tissues, and is rapidly
translocated to all parts of the plant, primarily acropetally. Uses An insecticide with quick
initial action and short residual effect. It penetrates plant tissue and is rapidly translocated,
controlling sucking insects (especially aphids) and certain Diptera in field and glasshouse
crops. Application rates for Hostaquick (550 g/l EC): on fruit trees 0.05%, against woolly
aphids 0.1%, on vegetables and ornamentals 0.05%, in cereals 0.40.5 l/ha, on glasshouse
crops 0.050.1%. Also effective against ectoparasites (fleas, lice, mites and ticks) of cattle,
dogs, pigs, sheep and pets. Phytotoxicity Non-phytotoxic when used as directed, except
to some varieties of apple, sweet cherry, and rose. Formulation types EC.
PRODUCTS:
Discontinued products Hostaquick* (crop protection use) (Aventis); Ragadan*
(veterinary use) (Intervet); Discontinuedmixtures Decisquick* (+deltamethrin) (Bayer
CropScience).
Oral Acute oral LD50 for rats 96121, dogs 5001000 mg/kg b.w. daily. Skin and eye
Acute percutaneous LD50 for rats >2000 mg/kg. Mild eye irritant. Inhalation LC50 (4 h) for
rats 0.95 mg/l air. NOEL (2 y) for dogs 12, rats 15 mg/kg diet. ADI/RfD (BfR) 0.002 mg/kg
b.w. [1997]. Toxicity Class WHO (a.i.) Ib. ECClassification T; R25| N; R50, R53| concn.
dep.
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 1755 mg/kg (depending on carrier and sex)
for pure a.i. Fish LC50 (96 h) for trout 0.056, carp 24 mg/l. Daphnia LC50 (48 h) 2.2 g/l.
Algae EC50 (72 h) 20 mg/l. Bees Toxic to bees. Worms LC50 (14 d) for Eisenia foetida
98 mg/kg dry, artificial soil. Other beneficial Harmless to Chrysoperla larvae.
heptenophos 315
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 90% is excreted in the urine and 6% in the
faeces in metabolised form within 6 days. Plants Four days after application to lettuce,
the compound is completely metabolised to polar, water-soluble compounds without
accumulation of any intermediate. Soil/Environment In soil, rapidly degraded by micro-
organisms, DT50 (field) 1.4 d, DT90 (field) 4.6 d, depending on temperature and soil type;
no accumulation. In lab. (aerobic), DT50 <4 h, DT90 40 h (20C). Degradation in water
phase of water sediment system is very quick, DT50 2777 h.
heptopargil
CH3
H3C CH3
N CH2
O
C
CH
NOMENCLATURE:
Common name heptopargil (BSI, E-ISO, (m) F-ISO)
IUPACname (E)-(1RS,4RS)-bornan-2-one O-prop-2-ynyloxime
Chemical Abstracts name ()-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one O-2-
propynyloxime CASRN[73886289] DevelopmentcodesEGYT 2250
SmilescodeCC1(C)C2CCC1(C)C(=NOCC#C)C2
PHYSICAL CHEMISTRY: Mol. wt. 205.3 M.f. C13H19NO Form Pale yellow oil.
B.p. 95C /1 mmHg S.g./density 0.9867 (20C) Solubility In water 1 g/l (20C).
Miscible with protic and aprotic organic solvents.
COMMERCIALISATION:
History Plant growth regulator reported by A. Kis-Tams etal. (Proc. Br. Crop Prot. Conf.
Weeds, 1980, I, 173). Introduced by EGYT Pharmacochemical Works. Patents US 4244888
APPLICATIONS:
Biochemistry Acts by chlorophyll stabilization. Uses A crop yield enhancer applied as
seed treatment for maize, rice and sugar beet and by pre-emergence or post-emergence
applications in beans, alfalfa, maize, peas, sunflowers and various vegetables. Applied at
48 g/100 cwt seed, or 0.251.0 kg/ha. Formulation types EC; LS .
PRODUCTS:
Discontinued products Limbolid* (EGYT).
Oral Acute oral LD50 for male rats 2100, female rats 2141 mg/kg. Inhalation LC50 for rats
>1.4 mg/l air. Toxicity Class WHO (a.i.) III
316 heptopargil
ECOTOXICOLOGY:
Fish Moderately toxic to fish. Bees Moderately toxic to bees.
Hercules 3944
Fungicide
NOMENCLATURE:
IUPACname 5-chloro-4-phenyl-1,2-dithiol-3-one
Chemical Abstracts name 5-chloro-4-phenyl-3H-1,2-dithiol-3-one
CASRN[2425050] DevelopmentcodesHercules 3944
SmilescodeClc1ssc(=O)c1c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 228.7 M.f. C9H5ClOS2
COMMERCIALISATION:
History Fungicide reported by W. R. Sitterly (Plant Dis. Rep., 1961, 45, 200). Introduced by
Hercules Inc.
hexachloroacetone
Herbicide
NOMENCLATURE:
Common name HCA (WSSA); hexachloroacetone (E-ISO); hexachloracetone (F-ISO);
all are accepted in lieu of a common name
IUPACname hexachloroacetone
Chemical Abstracts name 1,1,1,3,3,3-hexachloro-2-propanone CASRN[116165]
ECno2041295 DevelopmentcodesGC 1106 SmilescodeClC(Cl)(Cl)C(=O)
C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. isc.85%. Mol. wt. 264.8 M.f. C3Cl6O Form Pale yellow liquid.
B.p. 203.6C S.g./density 1.74 Solubility Slightly soluble in water (25C). Miscible with
aliphatic and aromatic hydrocarbons, chlorobenzene, methanol, isopropanol, vegetable oils.
Stability Reacts slowly with water to form chloroform and trichloroacetic acid, a reaction
accelerated by alkali.
COMMERCIALISATION:
History Herbicide introduced by Allied Chemical Corp., Agricultural Division (later
Hopkins Chemical Co.). Patents US 2635117; US 2764479
APPLICATIONS:
ModeofactionTotal herbicide. Uses Used in combinations with petroleum oil or other
herbicides for total weed control in non-cropped land, at 5.522.5 kg/ha.
hexachloroacetone 317
PRODUCTS:
Discontinuedmixtures Urox 379* (+bromacil) (Allied).
ANALYSIS:
Product analysis is by i.r. spectrometry.
Oral Acute oral LD50 for male albino rats 13701730 mg/kg. Skin and eye Acute
percutaneous LD50 for male albino rabbits 19004060 mg/kg. Other It is slightly
lachrymatory. Toxicity Class WHO (a.i.) O ECClassification Xn; R22| N; R51, R53
hexadecyl cyclopropanecarboxylate
Acaricide
NOMENCLATURE:
IUPACname hexadecyl cyclopropanecarboxylate (I)
Chemical Abstracts name (I) Other names cycloprate* (rejected common
name proposal) CASRN[54460467] DevelopmentcodesZR 856; TF-5166
SmilescodeCCCCCCCCCCCCCCCCOC(=O)C1CC1
COMMERCIALISATION:
History Acaricide evaluated by Zoecon Corp. (later Sandoz AG).
PRODUCTS:
Discontinued products Zardex* (Sandoz).
hexafluoroacetone trihydrate
NOMENCLATURE:
IUPACname (i) hexafluoroacetone trihydrate; (ii) 1,1,1,3,3,3-hexafluoropropane-2,2-diol
dihydrate
Chemical Abstracts name 1,1,1,3,3,3-hexafluoro-2-propanone; 1,1,1,3,3,3-hexafluoro-
2,2-propanediol CASRN[34202692] for (i); [677714] for the diol
DevelopmentcodesGC 7887
PHYSICAL CHEMISTRY: Mol. wt. 220.1 M.f. C3H6F6O4 Form Colourless liquid.
B.p.c.105C S.g./density 1.59 Solubility Soluble in water. Insoluble in most organic
solvents.
COMMERCIALISATION:
History Herbicide introduced by Allied Chemical Corp., Agricultural Division (later
Hopkins Agricultural Chemical Co.). Patents GB 1026036
318
hexafluoroacetone trihydrate
APPLICATIONS:
ModeofactionTotal herbicide, desiccant and plant growth regulator. Uses At
1123 kg/ha, controls annual and perennial weeds, and woody plants, on uncropped land.
At 11 kg/ha it destroys potato haulm. Formulation types DC.
ICSC.057 (hexafluoroacetone; 2000).
Oral Acute oral LD50 for male albino rats 176204 mg/kg. Skin and eye Acute
percutaneous LD50 for male albino rabbits 108118 mg/kg.
hexaflurate
Herbicide
NOMENCLATURE:
Common name hexaflurate (WSSA)
IUPACname potassium hexafluoroarsenate
Chemical Abstracts name potassium hexafluoroarsenate(1-) CASRN[17029220]
Smilescode[K+].F[As-](F)(F)(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 228.0 M.f. AsF6K Form Colourless crystals.
M.p.436C (decomp.) V.p. Non-volatile. S.g./density 3.29 Solubility In water 210 g/kg
(25C, endothermic). Stability Resistant to uv radiation and to microbial breakdown.
F.p. Non-flammable
COMMERCIALISATION:
History First prepared by M. C. Marignac (Ann. Chem. Pharm., 1867, 145, 237), evaluated
as a herbicide by Pennwalt Corp. and Dow Chemical Co. Patents US 3189428; US
3419382
APPLICATIONS:
ModeofactionSelective and systemic herbicide, absorbed by the roots. Uses Effective
at 2 kg/ha against prickly pear and other Opuntia spp.
PRODUCTS:
Discontinued products Nopalmate* (Pennwalt).
ANALYSIS:
Product analysis by measurement of fluoride by titration with thorium nitrate.
Arsenic and arsenic compounds are reviewed in EHC 224 (2001).
rabbits >10000 mg/kg. Moderately irritating to eyes; not irritating to skin (rabbits).
NOEL In 90 d feeding trials on rats, no harmful effect was observed at 1000 mg/kg diet.
hexaflurate 319
Toxicity Class WHO (a.i.) O ECClassification Not specified, but arsenic compounds in
general (with exceptions) are assigned T; R23/25| N; R50, R53 (concentration-dependent)
hexylthiofos
Fungicide
NOMENCLATURE:
Common name hexylthiofos (BSI, E-ISO, (m) F-ISO)
IUPACname O-cyclohexyl O,S-diethyl phosphorothioate (I)
Chemical Abstracts name (I) CASRN[41495674] unstated stereochemistry
DevelopmentcodesNTN 3318 SmilescodeCCOP(=O)(OC1CCCCC1)SCC
COMMERCIALISATION:
History Fungicide evaluated by Bayer AG.
holosulf
NOMENCLATURE:
Common name holosulf (BSI, E-ISO, (m) F-ISO)
IUPACname 2-chloroethanesulfinic acid (I)
Chemical Abstracts name (I) CASRN[21780041] DevelopmentcodesHOL 1302
SmilescodeOS(=O)CCCl
COMMERCIALISATION:
History Plant growth regulator evaluated by Bayer AG.
APPLICATIONS:
Biochemistry Ethylene generator.
2-hydrazinoethanol
HOCH2CH2NHNH2
NOMENCLATURE:
IUPACname 2-hydrazinoethanol; 2-hydroxyethylhydrazine
Chemical Abstracts name 2-hydrazinoethanol Other names BOH CASRN[109
842] SmilescodeNNCCO
320 2-hydrazinoethanol
PHYSICAL CHEMISTRY: Mol. wt. 76.1 M.f. C2H8N2O Form Colourless liquid.
M.p.-70C B.p. 110130C /17.5 mmHg Solubility Miscible with water and lower
alcohols (room temperature). Stability Stable in the cool and in the dark. Dilute solutions
easily oxidised.
COMMERCIALISATION:
History Introduced as a plant growth regulator by Olin Corp.
APPLICATIONS: Uses Used to promote flowering of Bromeliaceae.
Formulation types SL .
PRODUCTS:
Discontinued products Omaflora* (Olin).
1-hydroxy-1H-pyridine-2-thione
Bactericide, fungicide
NOMENCLATURE:
IUPACname 1-hydroxy-1H-pyridine-2-thione (i); tautomeric with pyridine-2-thiol
1-oxide (ii)
Chemical Abstracts name 1-hydroxy-2(1H)-pyridinethione (i); 2-pyridinethiol
1-oxide (ii) CASRN[1121308] (i); [1121319] (ii); [32255906] manganese(II)
derivative; [13463417] zinc derivative DevelopmentcodesOM 1563 (zinc salt)
SmilescodeOn1ccccc1=S
PHYSICAL CHEMISTRY: Mol. wt. 127.2 M.f. C5H5NOS Stability Forms strongly
chelated metal derivatives.
COMMERCIALISATION:
History Compounds reported by E. Shaw etal. (J. Am. Chem. Soc., 1950, 72, 4362).Various
metal salts investigated as fungicides (M. Szkolnik & J. M. Hamilton, Plant Dis. Rep., 1957, 41,
289, 293, 301) and evaluated by the Olin Mathieson Chemical Corp.
PRODUCTS:
Discontinued products Omadine* (Olin); Omadine OM1563* (zinc derivative)
(Olin); Omadine OM1564* (manganese(II) derivative) (Olin); Omadine OM1565* (iron
derivative) (Olin).
hyquincarb
Insecticide
NOMENCLATURE:
Common name hyquincarb (BSI, E-ISO, (m) F-ISO)
IUPACname 5,6,7,8-tetrahydro-2-methyl-4-quinolyl dimethylcarbamate
Chemical Abstracts name 5,6,7,8-tetrahydro-2-methyl-4-quinolinyl dimethylcarbamate
hyquincarb 321
CASRN[56716213] DevelopmentcodesHoe 25 682

SmilescodeCN(C)C(=O)Oc1cc(C)nc2CCCCc12
COMMERCIALISATION:
History Insecticide reported by K-D. Bock (Proc. Br. Crop. Prot. Conf. - Pests Dis., 1977, 3,
1017). Evaluated by Hoechst AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide. Uses For
use against aphids.
ICIA0858
Fungicide
O
C
NH
N OCH3
NOMENCLATURE:
Chemical Abstracts name N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide
CASRN[112860045] DevelopmentcodesICIA0858; SC-0858
SmilescodeCOc1ccc(NC(=O)C2CC2)cn1
COMMERCIALISATION:
History Fungicide evaluated by Zeneca Agrochemicals.
APPLICATIONS: Uses Evaluated as a broad-spectrum fungicide.
2-imidazolidone
Insecticide
NOMENCLATURE:
IUPACname 2-imidazolidone; imidazolidin-2-one
Chemical Abstracts name 2-imidazolidinone Other names ethyleneurea
CASRN[120934] SmilescodeO=C1NCCN1
M.p.131132C Solubility Readily soluble in water.
COMMERCIALISATION:
History Insect growth regulator reported by H. G. Simkover (J. Econ. Entomol., 1964, 57,
574). Evaluated by Shell Development Co. Patents US 3242044
322 2-imidazolidone
APPLICATIONS:
ModeofactionInsect growth regulator.
Oral Acute oral LD50 for mice >5000 mg/kg.
inabenfide
O
N C
NH Cl
HO CH
NOMENCLATURE:
Common name inabenfide (BSI, E-ISO, (m) F-ISO)
IUPACname 4-chloro-2-(-hydroxybenzyl)isonicotinanilide
Chemical Abstracts name N-[4-chloro-2-(hydroxyphenylmethyl)phenyl]-
4-pyridinecarboxamide CASRN[82211243] unstated stereochemistry
DevelopmentcodesCGR-811 (Chugai) SmilescodeOC(c1ccccc1)c2cc(Cl)
ccc2NC(=O)c3ccncc3
PHYSICAL CHEMISTRY: Mol. wt. 338.8 M.f. C19H15ClN2O2 Form Pale yellow-
brown or colourless crystals. M.p.210212C V.p. 0.063 mPa (20C) Kow logP =
3.13 Solubility In water 1 mg/l (30C). In acetone 3.6, ethyl acetate 1.43, xylene 0.58,
methanol 2.35, ethanol 1.61, chloroform 0.59, DMF 6.72, acetonitrile 0.58, tetrahydrofuran
1.61, hexane 8 104 (all in g/l, 30C). Stability Stable to heat and sunlight. Slightly
unstable in alkaline media; after 2 weeks at 40C, hydrolysed 16.2% (pH 2), 49.5% (pH 5),
83.9% (pH 7), 100% (pH 11).
COMMERCIALISATION:
History Plant growth regulator reported by K. Nakamura (Jpn. Pestic. Inf., 1987, No. 51,
p. 23). Introduced in Japan (1986) by Chugai Pharmaceutical Co., Ltd (agrochemical
interests now Eiko Kasei Co. Ltd). Patents EP 48998; US 4377407; JP 6341393
Manufacturers Dongbu HiTek; Eiko Kasei
APPLICATIONS:
Biochemistry Inhibits gibberellin biosynthesis. ModeofactionPlant growth regulator
which shortens lower internodes and upper leaf blades. Uses Used to increase resistance
to lodging in rice, being applied to the soil surface under submerged conditions, at
1.52.4 kg/ha. Phytotoxicity Non-phytotoxic to rice. Formulation types GR; WP.
inabenfide 323
PRODUCTS:
Discontinued products Seritard* (Eiko Kasei).
ANALYSIS:
Product and residue analysis by hplc.
J. Pestic. Sci., 1988, 13, 391394.
LD50 for rats and mice >5000 mg/kg. Not a skin or eye irritant (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >0.46 mg/l air. NOEL In 6 mo
and 2 y toxicity studies on dogs and rats, no ill-effects were observed. In reproductive
toxicity (3 generations) and teratogenicity studies on rats and rabbits, no abnormalities
were observed. Other Not mutagenic in Ames assay. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp >30, grey mullet 11 mg/l. Daphnia LC50 (3 h) >30 mg/l.
ENVIRONMENTAL FATE:
Animals The major urinary metabolite in the rat is 4-hydroxyinabenfide (H. Kinoshita et
al., Xenobiotica, 1987, 17, 925). Plants Metabolised to inabenfide ketone.
Soil/Environment Under Japanese paddy field conditions, DT50c.4 mo.
iodobonil
Herbicide
NOMENCLATURE:
Common name iodobonil (BSI, E-ISO, (m) F-ISO)
IUPACname allyl 4-cyano-2,5-di-iodophenyl carbonate; 4-(allyloxycarbonyloxy)-3,5-di-
iodobenzonitrile
Chemical Abstracts name 4-cyano-2,6-di-iodophenyl 2-propenyl carbonate
CASRN[25671458] SmilescodeIc1cc(C#N)cc(I)c1OC(=O)OCC=C
PHYSICAL CHEMISTRY: Mol. wt. 455.0 M.f. C11H7I2NO3
COMMERCIALISATION:
History Herbicide evaluated by C. H. Boehringer Sohn (later Shell Agrar GmbH).
ipazine
Herbicide
NOMENCLATURE:
Common name ipazine (BSI, E-ISO, (f) F-ISO, WSSA)
324 ipazine
IUPACname 6-chloro-N2,N2-diethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine; 2-chloro-4-

diethylamino-6-isopropylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N,N-diethyl-N-(1-methylethyl)-1,3,5-triazine-2,4-
diamine CASRN[1912250] DevelopmentcodesG 30 031
SmilescodeCCN(CC)c1nc(Cl)nc(NC(C)C)n1
COMMERCIALISATION:
History Herbicide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinued products Gesabal* (Ciba-Geigy).
iprymidam
Herbicide
NOMENCLATURE:
Common name iprymidam (BSI, E-ISO, (m) F-ISO)
IUPACname 6-chloro-N4-isopropylpyrimidine-2,4-diamine
Chemical Abstracts name 6-chloro-N4-(1-methylethyl)-2,4-pyrimidinediamine
CASRN[30182242] DevelopmentcodesSAN 52 123H
SmilescodeCC(C)Nc1cc(Cl)nc(N)n1
COMMERCIALISATION:
History Herbicide evaluated by Sandoz AG.
IPSP
Insecticide
CH3CH2 O
S
S
CH2
P[OCH(CH3)2]2
S
IRAC1B
NOMENCLATURE:
Common name IPSP (JMAF)
IUPACname S-ethylsulfinylmethyl O,O-diisopropyl phosphorodithioate
IPSP 325
Chemical Abstracts name S-[(ethylsulfinyl)methyl] O,O-bis(1-methylethyl)

phosphorodithioate CASRN[5827054] DevelopmentcodesPSP-204 (Hokko)
SmilescodeCCS(=O)CSP(=S)(OC(C)C)OC(C)C
PHYSICAL CHEMISTRY:
Composition Tech. is 90%. Mol. wt. 304.4 M.f. C9H21O3PS3 Form Yellow liquid (tech.).
V.p. 2 mPa (27C) (tech.) S.g./density 1.1696 (20C, tech.) Solubility In water
1.5 g/l (15C). In hexane 71 g/l (20C); freely soluble in acetone and xylene. Stability
DT50 (25C) 4 d (pH 7), 3 d (pH 9). Stable up to 100C.
COMMERCIALISATION:
History Insecticide reported by D. Murrayama etal. (Mem. Fac. Agric. Hokkaido Univ.,
1966, 6, 73). Introduced by Hokko Chemical Industry Co., Ltd. Patents JP 531126; US
3408426; GB 1068628
APPLICATIONS:
Biochemistry Cholinesterase inhibitor ModeofactionSystemic insecticide.
Uses Control of aphids on potatoes and other vegetables. Formulation types GR .
PRODUCTS:
Discontinued products Aphidan* (Hokko).
ANALYSIS:
Product by tlc with colorimetric determination. Residues by glc with FPD.
Oral Acute oral LD50 for male rats 25, male mice 320 mg/kg. Skin and eye Acute
percutaneous LD50 for male rats 28, female mice 1300 mg/kg. Toxicity Class WHO (a.i.) O
ECClassification T+; R27| T; R25| N; R50, R53| concn. dep.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 20 mg/l.
isamidofos
Nematicide
NOMENCLATURE:
Common name isamidofos (BSI, E-ISO, (m) F-ISO)
IUPACname O-ethyl S-(N-methylcarbaniloylmethyl) N-isopropylphosphoramidothioate
Chemical Abstracts name O-ethyl S-[2-(methylphenylamino)-2-
oxoethyl] (1-methylethyl)phosphoramidothioate CASRN[66602877]
DevelopmentcodesHoe 36 275
SmilescodeCCOP(=O)(NC(C)C)SCC(=O)N(C)c1ccccc1
326 isamidofos

COMMERCIALISATION:
History Nematicide evaluated by Hoechst AG.
isazofos
S
(CH3)2CH
P(OCH2CH3)2
N N
O
Cl N
IRAC1B
NOMENCLATURE:
Common name isazofos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname O-5-chloro-1-isopropyl-1H-1,2,4-triazol-3-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[5-chloro-1-(1-methylethyl)-1H-1,2,4-triazol-3-
yl] O,O-diethyl phosphorothioate CASRN[42509808] ECno2558638
DevelopmentcodesCGA 12 223 SmilescodeCCOP(=S)(OCC)Oc1nc(Cl)n(n1)C(C)C
PHYSICAL CHEMISTRY: Mol. wt. 313.7 M.f. C9H17ClN3O3PS Form Yellow liquid.
B.p. 120C (36 Pa) V.p. 7.45 mPa (20C) Kow logP = 2.99 Henry 1.39 10-2 Pa m3
mol1 (calc.) S.g./density 1.23 (20C) Solubility In water 168 mg/l (20C). Miscible
with organic solvents, e.g. chloroform, methanol, benzene. Stability Hydrolysed more
rapidly in alkalis than in acids; DT50 (calc.) (20C) 85 d (pH 5), 48 d (pH 7), 19 d (pH 9).
Decomposes above 200C.
COMMERCIALISATION:
History Insecticide and nematicide reported by D. Dawes etal. (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1974, 39, 727) and F. Bachmann & D. Dawes (ibid., p. 801). Developed by Ciba-
Geigy AG (later Novartis Crop Protection AG). Patents BE 792452; GB 1419131; GB
1419132 Manufacturers Novartis
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNematicide and systemic
insecticide with contact and stomach action. Uses A soil-applied nematicide used on
bananas (against Radopholus similis and Cosmopolites sordidus), citrus, cotton, beet, maize,
rice, vegetables, sugar cane, and in turf against soil-dwelling insects.
Phytotoxicity Phytotoxic to potatoes and tobacco. Formulation types EC; GR .
PRODUCTS:
Discontinued products Brace* (Ciba-Geigy); Miral* (Novartis); Triumph* (Ciba-
Geigy); Victor* (Ciba-Geigy).
isazofos 327
ANALYSIS:
male rats >3100, female rats 118 mg/kg. Mild skin irritant; very slight eye irritant (rabbits).
Inhalation LC50 (4 h) for rats 0.24 mg/l air. NOEL (90 d) for rats 2 mg/kg diet (0.2 mg/kg
daily), for dogs 2 mg/kg diet (0.05 mg/kg daily). ADI/RfD (EPA) 0.00002 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassification T+; R26| T; R24/25|
Xn; R48/20| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Toxic to birds. Acute oral LD50 for mallard ducks 61, bobwhite quail 11.1 mg/kg. LC50
(8 d) for bobwhite quail 81 ppm. Fish LC50 (96 h) for bluegill sunfish 0.01, carp 0.22, trout
0.0080.019 mg/l. Daphnia LC50 (48 h) 0.0014 mg/l. Bees Toxic to honeybees.
ENVIRONMENTAL FATE:
Animals It is extensively metabolised and rapidly excreted, primarily in the urine. No
accumulation takes place in the body. Soil/Environment DT50 10 d (lab.).
isobenzan
Insecticide
IRAC2A
NOMENCLATURE:
Common name telodrin (JMAF); isobenzan (BSI, E-ISO, (m) F-ISO)
IUPACname 1,3,4,5,6,7,8,8-octachloro-1,3,3a,4,7,7a-hexahydro-4,7-
methanoisobenzofuran (I)
DevelopmentcodesSD 4402; WL 1650; CP 14957
SmilescodeClC1OC(Cl)C2C1C3(Cl)C(=C(Cl)C2(Cl)C3(Cl)Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 411.8 M.f. C9H4Cl8O
COMMERCIALISATION:
History Insecticide evaluated by Shell International Chemical Co. Manufactured in the
Netherlands from 1958 to 1965.
APPLICATIONS:
PRODUCTS:
Discontinued products Telodrin* (Shell).
328 isobenzan

EHC 129 (1991). HSG 61 (1991).
Toxicity Class WHO (a.i.) O ECClassification T+; R27/28| N; R50
ENVIRONMENTAL FATE:
EHC 129 concluded isobenzan is a significant hazard to the environment and to exposed
workers.
isocarbamid
Herbicide
NOMENCLATURE:
Common name isocarbamid (BSI, E-ISO); isocarbamide ((m) F-ISO, WSSA)
IUPACname N-isobutyl-2-oxoimidazolidine-1-carboxamide
Chemical Abstracts name N-(2-methylpropyl)-2-oxo-1-imidazolidinecarboxamide
CASRN[30979487] DevelopmentcodesBAY MNF 0166
SmilescodeCC(C)CNC(=O)N1CCNC1=O
PHYSICAL CHEMISTRY: Mol. wt. 185.2 M.f. C8H15N3O2 Form Colourless crystalline
solid. M.p.9596C V.p. <13000 mPa (50C) Solubility In water 1.3 g/l (20C). In
cyclohexanone 130, dichloromethane 281 (both g/kg, 20C). Stability Stable in alkaline
and acid media.
COMMERCIALISATION:
History Herbicide reported by L. Eue etal. (Proc. Br.Weed Control Conf., 10th, 1970, 2, 610).
Introduced by Bayer AG. Patents DE 1795117; US 3875180
APPLICATIONS:
ModeofactionSelective herbicide. Uses A selective herbicide for use in sugar beet and
fodder beet at rates of 34 kg/ha, in mixture with lenacil, for pre-em. application.
PRODUCTS:
Discontinuedmixtures Merpelan AZ* (+lenacil) (Bayer); Terratop* (+lenacil) (Bayer).
ANALYSIS:
Residues determined by glc (H. J. Jarczyk, Pflanz.-Nachr. Bayer (Engl. Ed.), 1974, 27, 130).
Oral Acute oral LD50 for male rats >2500, female dogs >500 mg/kg. Skin and eye Acute
percutaneous LD50 for male rats >500 mg/kg. NOEL (90 d) for rats 800 mg/kg diet, for
dogs >5000 mg/kg diet. Toxicity Class WHO (a.i.) U
isocarbamid 329
isocil
Herbicide
NOMENCLATURE:
Common name isocil (BSI, E-ISO, (m) F-ISO, ANSI, WSSA); isoprocil (France, Republic of
South Africa)
IUPACname 5-bromo-3-isopropyl-6-methyluracil
Chemical Abstracts name 5-bromo-6-methyl-3-(1-methylethyl)-2,4(1H,3H)-
pyrimidinedione CASRN[314421] DevelopmentcodesDuPont Herbicide 82
SmilescodeCC(C)n1c(=O)[nH]c(C)c(Br)c1=O
PHYSICAL CHEMISTRY: Mol. wt. 247.1 M.f. C8H11BrN2O2 Form Colourless solid.
M.p.158159C Solubility In water 2.1 g/l (25C). Soluble in alkali, acetone, acetonitrile,
ethanol. Stability Stable 159C but decomposed by concentrated acids.
COMMERCIALISATION:
History Herbicide reported by H. C. Bucha etal. (Science, 1962, 137, 537). Introduced by
E. I. du Pont de Nemours & Co. Patents US 3235357
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. ModeofactionTotal herbicide. Uses At
1318 kg/ha, for control of perennial grasses and on non-cropped land.
PRODUCTS:
Discontinued products Hyvar* (DuPont).
Oral Acute oral LD50 for male albino ratsc.3400 mg/kg. Toxicity Class WHO (a.i.) O
isodrin
Insecticide
IRAC2A
NOMENCLATURE:
Common name isodrin (BSI); isodrine ((f) France)
IUPACname (1R,4S,5R,8S)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-
dimethanonaphthalene
Chemical Abstracts name (1,4,4a,5,8,8a)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-
hexahydro-1,4:5,8-dimethanonaphthalene CASRN[465736] ECno2073662
DevelopmentcodesCompound 711; SD-3418
SmilescodeClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 364.9 M.f. C12H8Cl6
330 isodrin
COMMERCIALISATION:
History Insecticide evaluated by Shell International Chemical Co.
APPLICATIONS:
Toxicity Class WHO (a.i.) O ECClassification T+; R26/27/28| N; R50, R53| concn. dep.
isofenphos
Insecticide
(CH3)2CHO O S
C
OPOCH2CH3
NHCH(CH3)2
IRAC1B
NOMENCLATURE:
Common name isofenphos (BSI, E-ISO); isophenphos ((m) F-ISO)
IUPACname O-ethyl O-2-isopropoxycarbonylphenyl N-isopropylphosphoramidothioate;
isopropyl O-[ethoxy-N-isopropylamino(thiophosphoryl)]salicylate
Chemical Abstracts name 1-methylethyl 2-[[ethoxy[(1-methylethyl)amino]
phosphinothioyl]oxy]benzoate CASRN[25311711] ECno2468141
DevelopmentcodesBAY SRA 12 869; BAY 92114 (Bayer) SmilescodeCCOP(=S)
(NC(C)C)Oc1ccccc1C(=O)OC(C)C
PHYSICAL CHEMISTRY: Mol. wt. 345.4 M.f. C15H24NO4PS Form Colourless oil;
(tech. has a characteristic smell). V.p. 0.22 mPa (20C); 0.44 mPa (25C) Kow logP = 4.04
(21C) Henry 4.2 103 Pa m3 mol1 (20C) S.g./density 1.131 (20C) Solubility In
water 18 mg/l (20C). In isopropanol, hexane, dichloromethane, toluene >200 g/l (20C).
Stability DT50 for aqueous hydrolysis 2.8 y (pH 4), >1 y (pH 7), >1 y (pH 9) (22C).
Photodegradation on soil surface in the laboratory is extremely rapid. Under natural light,
photodegradation is not so fast. F.p. >115C (tech.)
COMMERCIALISATION:
History Insecticide reported by B. Homeyer (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1974, 39, 789). Introduced by Bayer AG. Patents DE 1668047 Manufacturers Bayer
APPLICATIONS:
contact and stomach action. Translocated from roots to a limited extent. Uses Control of
cabbage root flies, carrot flies, onion flies, corn rootworms, white grubs, wireworms, and
other soil insects in vegetables, oilseed rape, maize, bananas, turf, sugar cane, and other
isofenphos 331
crops; and also controls thrips in citrus and onions. Formulation types DS; EC; GR; WP.
PRODUCTS:
Discontinued products Amaze* (Bayer CropScience); Oftanol* (Bayer CropScience);
Pryfon* (Mobay); Discontinuedmixtures Oftanol T* (+thiram) (Bayer CropScience).
ANALYSIS:
Product analysis by glc with FID or TCD (CIPACHandbook, 1988, D, 114; AOACMethods,
18th Ed., 987.01). Residues determined by glc with FID (Man. Pestic. Residue Anal., p. 6; Anal.
Methods Residues Pestic., 1988, Part I, M5, M13; K. Wagner, Pflanz.-Nachr. Bayer (Engl. Ed.),
1976, 29, 67).
JMPR Evaln. I 66 (1992); JMPR Evaln. II 49 (1986). EU Status (1107/2009) Not approved,
Oral Acute oral LD50 for male and female ratsc.20, micec.125 mg/kg. Skin and eye Acute
percutaneous LD50 for male and female ratsc.70 mg/kg. Slightly irritating to eyes and skin
(rabbits). Inhalation LC50 (4 h) for male ratsc.0.5 mg/l, female rats 0.3 mg/l air (aerosol).
NOEL (2 y) for rats 1 mg/kg diet (0.05 mg/kg b.w.), dogs 2, mice 1 mg/kg diet.
ADI/RfD (JMPR) 0.001 mg/kg b.w. [1986]; (EPA) cRfD 0.00008 mg/kg b.w., however
subsequent re-evaluation by EPA would lead to a valuec.0.0003 mg/kg b.w. [1999].
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassification T; R24/25| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 8.7, mallard ducks 3236 mg/kg. Dietary LC50
(5 d) for bobwhite quail 145, mallard ducks 4908 mg/kg diet. Fish LC50 (96 h) for golden
orfe 6.49, bluegill sunfish 2.2, rainbow trout 3.3 mg/l. Daphnia LC50 (48 h) 0.00390.0073
mg/l. Algae ErC50 for Scenedesmus subspicatus 6.8 mg/l. Bees Toxic to bees.
Worms LC50 for Eisenia foetida 404 mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals For a study of metabolism in rats and in rat liver microsomal systems, see M.
Ueji & C. Tomizawa, J. Pestic. Sci., 1987, 12, 245, 269. Elimination is very quick; almost 95%
is excreted within 24 h, in urine and faeces. Plants The most important metabolites are
salicylic acid and dihydroxybenzol acid. Soil/Environment Mobility is medium to low.
Degradation in different soils is slow.
332 isofenphos
isofetamid
Fungicide
OH C H3
C H3
H 3C
O
H3C N
S
CH 3 O
CH
NOMENCLATURE: 3
Common name isofetamid (pa ISO)

IUPACname N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxoethyl]-3-methylthiophene-2-
carboxamide
Chemical Abstracts name N-[1,1-dimethyl-2-[2-methyl-4-(1-methylethoxy)
phenyl]-2-oxoethyl]-3-methyl-2-thiophenecarboxamide CASRN[875915789]
DevelopmentcodesKF5411
SmilescodeO=C(C(C)(C)NC(C1=C(C)C=CS1)=O)C2=CC=C(OC(C)C)C=C2C
isolane
Insecticide
NOMENCLATURE:
Common name isolane ((m) France)
IUPACname 1-isopropyl-3-methylpyrazol-5-yl dimethylcarbamate
Chemical Abstracts name 3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl
dimethylcarbamate CASRN[119380] ECno2043182
DevelopmentcodesG 23 611 SmilescodeCC(C)n1nc(C)cc1OC(=O)N(C)C
PHYSICAL CHEMISTRY: Mol. wt. 211.3 M.f. C10H17N3O2 Form Colourless liquid.
B.p. 105107C /0.33 mmHg V.p. 133 mPa (20C) S.g./density 1.07 (20C)
Solubility Miscible with water and most organic solvents. Stability Hydrolysed by
concentrated acids or alkali.
COMMERCIALISATION:
History Insecticide reported by H. Gysin (Proc. 3rd Int. Congr. Phytopharm., Paris, 1952).
Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 279533; CH 281967;
CH 282655
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact, systemic and fumigant
insecticide.
isolane 333
PRODUCTS:
Discontinued products Isolan* (Ciba-Geigy); Primin* (Geigy).
ANALYSIS:
Product analysis by acid hydrolysis and titrimetric estimation of the dimethylamine
produced (R. Suter et al., Fresenius Z. Anal. Chem., 1955, 147, 173). Residues determined by
colorimetry of the dimethylamine produced on hydrolysis (idem, ibid.; S. A. Hall et al., Anal.
Chem., 1951, 23, 1866).
Oral Acute oral LD50 for rats 1150 mg (in aqueous solution)/kg; for mice 918 mg/kg.
isomethiozin
Herbicide
NOMENCLATURE:
Common name isomethiozin (BSI, E-ISO); isom(thiozine) ((f) F-ISO)
IUPACname 6-tert-butyl-4-isobutylideneamino-3-methylthio-1,2,4-triazin-5(4H)-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-4-[(2-methylpropylidene)amino]-3-
(methylthio)-1,2,4-triazin-5(4H)-one CASRN[57052047] DevelopmentcodesBAY
DIC 1577 SmilescodeCSc1nnc(c(=O)n1N=CC(C)C)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 268.4 M.f. C12H20N4OS Form Colourless crystals.
M.p.159.3C V.p. 0.047 mPa (20C) Henry 1.26 103 Pa m3 mol1 (calc.) Solubility In
water 10 mg/kg (20C). In cyclohexanone 103, dichloromethane 152 (both g/kg, 20C).
COMMERCIALISATION:
History Herbicide reported by H. Hack (Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-
Dahlem, 1975, 165, 179; Pflanz.-Nachr. Bayer (Engl. Ed.), 1975, 28, 241). Introduced by Bayer
AG. Patents GB 1182801.
APPLICATIONS: Uses A post-em. herbicide in areas where there is a heavy infestation
of grass, also in winter wheat or, in combination with dichlorprop, in spring cereals (H.
Hack, Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-Dahlem, 1975, 165, 179; Pflanz.-Nachr.
Bayer (Engl. Ed.), 1975, 28, 241; W. Kolbe, ibid., p. 257). Formulation types WP.
PRODUCTS:
Discontinued products Tantizon* (Bayer); Discontinuedmixtures Tantizon Combi*
(+dichlorprop) (Bayer); Tantizon DP* (+dichlorprop) (Bayer).
ANALYSIS:
334 isomethiozin
Product analysis by i.r. spectrometry. Residues determined by glc with FID (H. J. Jarczyk,
ibid., p. 287).
Oral Acute oral LD50 for rats >10000, mice >2500 mg/kg. NOEL (90 d) for rats 100, dogs
500 mg/kg diet. Toxicity Class WHO (a.i.) U
isonoruron
Herbicide
NOMENCLATURE:
Common name isonoruron (BSI, E-ISO, (m) F-ISO)
IUPACname 1,1-dimethyl-3-(perhydro-4,7-methanoinden-1-yl)urea (i) and 1,1-dimethyl-
3-(perhydro-4,7-methanoinden-2-yl)urea (ii)
Chemical Abstracts name N,N-dimethyl-N-(octahydro-4,7-methano-1H-inden-1-yl)
urea (i) and N,N-dimethyl-N-(octahydro-4,7-methano-1H-inden-2-yl)urea (ii); N,N-
dimethyl-N-[octahydro-4,7-methanoinden-1(or 2)-yl]urea (i +ii) CASRN[28805789],
formerly [28346658] (i) +(ii)
PHYSICAL CHEMISTRY: Mol. wt. 222.3 M.f. C13H22N2O Form Colourless crystalline
powder. M.p.150180C Solubility In water 220 mg/l (20C). In acetone 11, benzene
78, chloroform 138, ethanol 175 (all in g/kg, 20C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Abstr. Int. Congr. Plant Prot., 1967, p. 446).
Introduced by BASF AG. Patents DE 1200062
APPLICATIONS:
ModeofactionSelective herbicide. Uses A mixture of isonoruron and brompyrazon
was used pre- and post- em. to control Alopecurus myosuroides, Apera spica-venti and
annual broad-leaved weeds in winter cereals at 3.44.0 kg formulation/ha. A mixture of
isonoruron and buturon was used pre-em. for potatoes at 3.44.5 kg formulation/ha.
PRODUCTS:
Discontinuedmixtures Basanor* (+brompyrazon) (BASF); Basfitox* (+buturon)
(BASF).
ANALYSIS:
Product analysis of Basfitox by uv spectrometry to determine buturon, and titration to
determine isonoruron.
>2500 mg Basfitox/kg; for rabbits >4000 mg/kg. NOEL No ill-effect was observed in
120 d feeding trials with rats receiving 400 mg/kg diet or with beagle dogs at 1600 mg/kg
diet. Toxicity Class WHO (a.i.) O
isonoruron 335
isopamphos
Fungicide
O
C9H19O(CH2)3NH3 CH3O P O
H
NOMENCLATURE:
IUPACname 3-nonyloxypropylammonium methylphosphonate
Other names izopamfos CASRN[94343563]
SmilescodeCCCCCCCCCOCCC[NH3+].COP(=O)[O-]
PHYSICAL CHEMISTRY:
Composition The material is a mixture of nonyl isomers. Mol. wt. 297.4
M.f. C13H32NO4P Form Colourless, viscous oil with an amine-like smell.
COMMERCIALISATION:
History Fungicide developed by Borsod.
APPLICATIONS:
ModeofactionProtectant and eradicant fungicide with some systemic activity. Uses As
a seed dresssing, effective alone or in combination with benzimidazole fungicides against
soil borne diseases on wheat or maize. As a foliar spray used against Peronospora spp.
and Phytophthora spp. in tobacco, tomatoes and potatoes. Formulation types SD; Water-
miscible.
PRODUCTS:
Discontinued products BF51* (Borsod).
10000 mg/kg. Inhalation Irritates mucous membranes.
isopolinate
Herbicide
NOMENCLATURE:
Common name isopolinate (BSI, E-ISO, (m) F-ISO)
IUPACname S-isopropyl azepane-1-carbothioate
Chemical Abstracts name (S)-(1-methylethyl) hexahydro-1H-azepine-1-carbothioate
CASRN[3134701] DevelopmentcodesR-4574; CH-83
SmilescodeCC(C)SC(=O)N1CCCCCC1
PHYSICAL CHEMISTRY: Mol. wt. 201.3 M.f. C10H19NOS
COMMERCIALISATION:
History Herbicide evaluated by Chugai Pharmaceutical Co. Ltd.
336 isopolinate
isopropalin
Herbicide
NO2
(CH3)2CH N[(CH2)2CH3]2
NO2
NOMENCLATURE:
Common name isopropalin (BSI, E-ISO, ANSI, WSSA); isopropaline ((f) F-ISO)
IUPACname 4-isopropyl-2,6-dinitro-N,N-dipropylaniline
Chemical Abstracts name 4-(1-methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine
CASRN[33820530] DevelopmentcodesEL-179
SmilescodeCCCN(CCC)c1c(cc(cc1[N+](=O)[O-])C(C)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 309.4 M.f. C15H23N3O4 Form Orange liquid;
(tech. is a red-orange liquid). V.p. 1.9 mPa (30C) Solubility In water 0.1 mg/l (25C). In
acetone, hexane, benzene, chloroform, diethyl ether, acetonitrile, methanol >1 (all in kg/l,
25C). Stability Stable in field use, though decomposed by uv light in laboratory studies.
F.p. 40.6C
COMMERCIALISATION:
History Herbicide reported by L. R. Guse (Proc. North Cent.Weed Control Conf., 1969, p.
44; G. J. Shoop, ibid., p. 19). Introduced in USA (1972) by Eli Lilly & Co. (later DowElanco).
Patents US 3257190
APPLICATIONS:
ModeofactionSelective herbicide, which affects physiological growth processes
associated with seed germination. Uses Control of broad-leaved weeds and grasses in
transplanted tobacco, and in direct-seeded tomatoes and capsicums. Applied pre-planting,
with soil incorporation at 12 kg/ha. Formulation types EC.
PRODUCTS:
Discontinued products Paarlan* (DowElanco).
ANALYSIS:
ANALYSIS: by glc (W. S. Johnson & O. D. Decherer, Anal. Methods Pestic. Plant Growth
Regul., 1976, 8, 369).
Oral Acute oral LD50 for mice and rats >5000 mg tech./kg; for dogs and rabbits >2000
mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Slightly irritating
to skin and eyes (rabbits). NOEL (90 d) for rats and dogs >250 mg/kg diet (15 mg/kg
isopropalin 337
b.w. for rats). ADI/RfD (EPA) 0.015 mg/kg b.w. [1986]. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens >2000, mallard ducks >2000, bobwhite quail >1000,
Japanese quail >1000 mg/kg. Fish LC50 (96 h) for goldfish >0.15, fathead minnows >0.1
mg/l. Bees LD50 for honeybees 0.011 mg/bee.
ENVIRONMENTAL FATE:
Plants In plants, there is no translocation of isopropalin or its degradation products to
the leaves or fruit, and no significant residues or specific metabolites have been detected.
Soil/Environment In soil, isopropalin is strongly adsorbed, with negligible leaching. In soils
DT50 <0.5 y. Micro-organisms are believed to play a role in the degradation, and there is
also some loss from volatilisation and from photodecomposition of material remaining on
the soil surface. See R. R. Romanowski Weed Sci. 1978, 26, 258.
isopyrimol
NOMENCLATURE:
Common name isopyrimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname 1-(4-chlorophenyl)-2-methyl-1-pyrimidin-5-ylpropan-1-ol
Chemical Abstracts name -(4-chlorophenyl)--(1-methylethyl)-5-pyrimidinemethanol
CASRN[55283697] SmilescodeCC(C)C(O)(c1ccc(Cl)cc1)c2cncnc2
COMMERCIALISATION:
History Plant growth regulator evaluated by Eli Lilly.
isothioate
Insecticide
IRAC1B
NOMENCLATURE:
Common name isothioate (BSI, JMAF, E-ISO, (m) F-ISO)
IUPACname S-2-isopropylthioethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name O,O-dimethyl S-[2-[(1-methylethyl)thio]
ethyl] phosphorodithioate Other names MITP CASRN[36614387]
DevelopmentcodesZ-7272 SmilescodeCOP(=S)(OC)SCCSC(C)C
PHYSICAL CHEMISTRY: Mol. wt. 260.4 M.f. C7H17O2PS3 Form Light yellowish-
338 isothioate
brown liquid, with an aromatic odour. V.p. 293 mPa (20C) Solubility In water 97 mg/l
(25C).
COMMERCIALISATION:
History Insecticide introduced by Nihon Nohyaku Co., Ltd. Patents JP 624714
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide, also with
vapour action. Uses Effective against aphids when used as a seed dressing or when applied
to foliage at 1.01.5 kg/ha. Formulation types Seed treatment; GR .
PRODUCTS:
Discontinued products Hosdon* (Nihon Nohyaku).
ANALYSIS:
Product analysis by tlc with estimation of the phosphorus in the spots by standard
colorimetric methods (T. Nakagawa & M. Kanauchi, Anal. Methods Pestic. Plant Growth Regul.,
1978, 10, 75) or by glc (idem, ibid.). Residue analysis by glc with FID (idem, ibid.).
percutaneous LD50 for male mice 240 mg/kg. Toxicity Class WHO (a.i.) Ib
ECClassification T; R24/25
isovaledione
Fungicide
NOMENCLATURE:
Common name isovaledione (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(3,5-dichlorophenyl)-1-isovalerylhydantoin
Chemical Abstracts name 3-(3,5-dichlorophenyl)-1-(3-methyl-1-oxobutyl)-
2,4-imidazolidinedione CASRN[70017935] DevelopmentcodesS-9373
SmilescodeCC(C)CC(=O)N1CC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
COMMERCIALISATION:
History Fungicide evaluated by Sumitomo Chemical Co., Ltd.
2-isovalerylindan-1,3-dione
Insecticide, rodenticide
NOMENCLATURE:
IUPACname 2-isovalerylindan-1,3-dione
Chemical Abstracts name 2-(3-methyl-1-oxobutyl)-1H-indene-1,3(2H)-dione
Other names PMP CASRN[83283]
2-isovalerylindan-1,3-dione 339
SmilescodeCC(C)CC(=O)C1C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY: Mol. wt. 230.3 M.f. C14H14O3 Form Yellow crystalline solid.
M.p.6768C Solubility Practically insoluble in water; soluble in most organic solvents.
Alkali metal and ammonium salts are soluble in water.
COMMERCIALISATION:
History Insecticide reported by L. B. Kilgore etal. (Ind. Eng. Chem., 1942, 34, 494).
Introduced by Kilgore Chemical Co. Patents US 2228170
APPLICATIONS: Uses A slow-acting insecticide. Structure-activity of some analogues
was discussed by L. B. Kilgore et al., (Ind. Eng. Chem., 1942, 34, 494).
PRODUCTS:
Discontinued products Valone* (Kilgore).
EHC 175 (1995).
isoxachlortole
Herbicide
O
N
C Cl
O
CH3 SO2
HRACF2 WSSA 27; isoxazole
NOMENCLATURE:
Common name isoxachlortole (BSI, E-ISO, (m) F-ISO)
IUPACname 4-chloro-2-mesylphenyl 5-cyclopropyl-1,2-oxazol-4-yl ketone
Chemical Abstracts name [4-chloro-2-(methylsulfonyl)phenyl](5-cyclopropyl-4-
isoxazolyl)methanone CASRN[141112063] DevelopmentcodesRPA 201735
(Rhne-Poulenc)
PHYSICAL CHEMISTRY: Mol. wt. 325.8 M.f. C14H12ClNO4S
COMMERCIALISATION:
History Herbicide evaluated by Rhne-Poulenc.
APPLICATIONS:
Biochemistry p-Hydroxyphenyl pyruvate dioxygenase inhibitor.
340 isoxachlortole
isoxapyrifop
Herbicide
N CH3
Cl O O CH C O
N
Cl O
NOMENCLATURE:
Common name isoxapyrifop (BSI, E-ISO, (m) F-ISO)
IUPACname (RS)-2-[2-(4-(3,5-dichloro-2-pyridyloxy)phenoxy)propionyl]isoxazolidine
Chemical Abstracts name ()-2-[2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]-1-
oxopropyl]isoxazolidine CASRN[87757184] DevelopmentcodesHOK-1566;
HOK-868 (both Hokko); RH-0898 (Rohm & Haas)
SmilescodeCC(Oc1ccc(Oc2ncc(Cl)cc2Cl)cc1)C(=O)N3CCCO3
PHYSICAL CHEMISTRY: Mol. wt. 383.2 M.f. C17H16Cl2N2O4 Form Colourless
crystals. M.p.121122C Kow logP = 3.36 Solubility In water 9.8 mg/l (25C).
COMMERCIALISATION:
History Herbicide reported by H. Ohyama etal. (Proc. Br. Crop Prot. Conf. Weeds, 1989, 1,
59). Introduced by Hokko Chemical Industry Co., Ltd.
Manufacturers Hokko
APPLICATIONS:
(ACCase). Inhibits the growth of meristematic tissue. ModeofactionSelective
systemic herbicide absorbed mainly through the foliage. Uses Post-emergence control
of grass weeds including Echinochloa, Brachiaria, Leptochloa, and Digitaria species in
rice, and Alopecurus, Setaria, and Alopecurus species in spring wheat and durum wheat.
Formulation types SC. WG .
percutaneous LD50 for rats >5000, for rabbits >2000 mg/kg. Slight irritation to eyes, non-
irritating to skin (rabbits). NOEL (1.5 y) for mice 0.02 mg/kg diet daily. Other Non-
mutagenic and non-teratogenic (rats and rabbits). Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail >5000 mg/kg. Not mutagenic in assays. Fish LC50
(96 h) for bluegill sunfish 1.4, rainbow trout 1.3 mg/l. Daphnia LC50 (6 h) >10 mg/l.
ENVIRONMENTAL FATE:
Plants Degrades rapidly in crops. Soil/Environment Degrades rapidly in soil to a
pyridyloxyphenoxypropionic acid metabolite (PPPA), which in turn degrades more slowly.
DT50 of the a.i. and PPPA in aerobic laboratory studies 14 d and 3090 d respectively.
isoxapyrifop 341
isoxathion
Insecticide
O N S
P(OCH2CH3)2
O
NOMENCLATURE:
Common name isoxathion (BSI, JMAF, E-ISO)
IUPACname O,O-diethyl O-5-phenylisoxazol-3-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(5-phenyl-3-isoxazolyl) phosphorothioate
CASRN[18854018] ECno2426248 DevelopmentcodesE-48; SI-6711 (Sankyo)
SmilescodeCCOP(=S)(OCC)Oc1cc(on1)c2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. is >93%. Mol. wt. 313.3 M.f. C13H16NO4PS Form Pale yellow liquid,
with an ester-like odour. B.p. 160C /0.15 mmHg V.p. <0.133 mPa (25C) Kow logP =
3.88 (pH 6.3) S.g./densityc.1.23 Solubility In water 1.9 mg/l (25C). Readily soluble in
organic solvents. Stability Unstable to alkalis. Decomposes at 160C. F.p. 210C
COMMERCIALISATION:
History Insecticide reported by N. Sampei etal. (Sankyo Kenkyusho Nempo, 1970, 22,
221). Introduced in Japan in 1972 by Sankyo Co., Ltd (agrochemicals interests now Mitsui
Chemicals Agro, Inc.). Patents JP 525850 Manufacturers Mitsui Chemicals Agro; Sankyo
Agro
APPLICATIONS:
stomach action. Uses Effective against Aphididae, Coccidae, Diaspididae and Margarodidae
(at 5001000 g/ha) in cabbages, citrus and ornamentals; against Agromyzidae, Cicadellidae,
Delphacidae, Ephydridae and Pyralidae (at 600900 g/ha) in paddy rice; against Coleoptera
(at 1.2 kg/ha) in turf and trees; and against Noctuidae and Pieridae (at 5001000 g/
ha) in pome fruit, citrus fruit and vegetables. Formulation types DP; EC; MG; WP.
PRODUCTS:
Discontinued products Karphos* (Sankyo Agro); Nekiriton K* (Sankyo Agro);
Discontinuedmixtures Sanritto Karufosu Funzai* (+simeconazole) (Sankyo Agro).
ANALYSIS:
Product analysis by glc with FID (T. Nakamura & K.Yamaoka, Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 83). Residues determined by glc with FPD or FTD (idem, ibid.).
342 isoxathion

EHC 63 (1986), a general review of organophosphorus insecticides.
Oral Acute oral LD50 for male rats 242, female rats 180, male mice 112, female mice 137
mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not irritant to skin.
Inhalation LC50 (4 h) for male rats 4.2, female rats 2.0 g/m3. NOEL (2 y) for rats 1.2 mg/
kg b.w.; (9 w) for man 0.03 mg/kg b.w. daily. ADI/RfD (FSC) 0.003 mg/kg. Other Non-
mutagenic, non-carcinogenic and non-teratogenic, and no adverse effects on reproduction.
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassification T; R24/25| N; R50,
R53
ECOTOXICOLOGY:
Birds LD50 for 7-day-old chickens 21.6, 50-day-old chickens 19.0 mg/kg. Fish LC50 (48 h)
for carp 1.7 mg/l. Daphnia LC50 (3 h) for D. pulex 0.0052 mg/l. Bees LC50 (contact)
0.082 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment DT50 in soil 37 d.
japonilure
Insect pheromone
CH3(CH2)7
H
O O
H

The sex pheromone of the Japanese beetle (Popillia japonica).
NOMENCLATURE:
IUPACname 5-[(Z)-dec-1-enyl]-(5R)-dihydrofuran-2(3H)-one
Chemical Abstracts name (R,Z)-5-(1-decenyl)dihydro-2(3H)-furanone
Other names nuranone CASRN[64726916], formerly [133494641], [77518
559] and [111192531]; [64726938] (S)- isomer SmilescodeCCCCCCCC/C=C\
[C@H]1CCC(=O)O1;without stereochemistry:CCCCCCCCC=CC1CCC(=O)O1
PHYSICAL CHEMISTRY: Mol. wt. 224.3 M.f. C14H24O2 Form Colourless, oily liquid.
B.p. 130134C /0.1 mmHg Kow logP = 0 (EPA Fact Sheet) Solubility In water <0.01%
(25C). Soluble in aromatic and aliphatic hydrocarbons (EPA Fact Sheet). Stability Stable
for 30 d at 50C; stable to light (48 h in sun) (EPA Fact Sheet). Specific rotation []D21
69.0 (c = 1.42, CHCl3) F.p. >200C
japonilure 343
COMMERCIALISATION:
History First registered in USA in 1979.
Manufacturers Ace; Nitto Denko
APPLICATIONS:
ModeofactionActs as an attractant. Uses Used for trapping Japanese beetle, in
combination with a floral lure (phenethyl propionate: eugenol: geraniol in the proportions
3:7:3).
Inhalation For rats >1.35 mg/l (aerosol) (EPA Fact Sheet).
jodfenphos
Acaricide, insecticide, ixodicide
Cl S
P(OCH3)2
I O
Cl
IRAC1B
NOMENCLATURE:
Common name iodofenphos (BSI, (m) F-ISO, BAN, ESA, Canada, New Zealand);
jodfenphos (E-ISO)
IUPACname O-2,5-dichloro-4-iodophenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(2,5-dichloro-4-iodophenyl) O,O-dimethyl
phosphorothioate CASRN[18181709] DevelopmentcodesC 9491
SmilescodeCOP(=S)(OC)Oc1cc(Cl)c(I)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 413.0 M.f. C8H8Cl2IO3PS Form Colourless
crystals. M.p.76C V.p. 0.106 mPa (20C) Henry <2.19 10-2 Pa m3 mol1 (calc.)
S.g./density 2.0 (20C) Solubility In water <2 mg/l (20C). In acetone, toluene 450,
dichloromethane 810, benzene 610, isopropanol 230, hexane 33, methanol, n-octanol 30 (all
in g/l, 20C). Stability Extremely stable in neutral, weakly acidic and weakly alkaline media.
Hydrolysed by strong acids and alkalis. Tech. stable to >160C.
COMMERCIALISATION:
History Insecticide and acaricide reported by B. C. Haddow & T. G. Marks (Proc. Br. Insectic.
Fungic. Conf., 5th, 1969, 2, 531). Introduced by Ciba AG (later Ciba-Geigy AG).
Patents BE 672431; GB 1057609
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of crawling and flying insects, e.g.
344 jodfenphos
flies, ants, silverfish, bedbugs, cockroaches, mosquitoes, mites, lice, ticks, fleas, Beetles, etc. in
public hygiene, storerooms and warehouses, household use, and animal and poultry houses.
Formulation types WP; SC. EC; DP .
PRODUCTS:
Discontinued products AlFRACon* (Ciba-Geigy); Elocril* (Ciba-Geigy); Nuvanol N*
(Ciba-Geigy); Waspex* (Rentokil).
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD or FPD (N. Burkhard & G.
Voss, Pestic. Sci., 1972, 3, 183).
EHC 63 (1986; a general review of organophosphorus insecticides). PDS 43 (1980).
Oral Acute oral LD50 for rats 2100, mice 3000, rabbits 2000, dogs 3000 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >2000, rabbits >500 mg/kg; slight irritant
to skin, not irritant to eyes of rabbits. Inhalation LC50 (6 h) for rats >0.246 mg/l.
NOEL (90 d) for rats 5 mg/kg diet (0.38 mg/kg daily), for dogs 15 mg/kg diet (0.45 mg/kg
daily). Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Non-toxic to birds. Fish LC50 (96 h) for rainbow trout 0.060.10, goldfish 1.001.33,
bluegill sunfish 0.420.75 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Following an oral dose of jodfenphos in rats, 92% was eliminated within 24 h.
For details of metabolites see F. R. Johannsen and C. Knowles (J. Econ. Entomol. 1970, 63,
693697).
kelevan
Insecticide
NOMENCLATURE:
Common name k(l) ((m) F-ISO); kelevan (BSI, E-ISO)
IUPACname ethyl 5-(1,2,3,4,6,7,8,9,10,10-decachloro-5-
hydroxypentacyclo[5.3.0.02,6.03,9.04,8]dec-5-yl)-4-oxovalerate; ethyl
5-(1,2,4,5,6,7,8,8,9,10-decachloro-3-hydroxypentacyclo[5.3.02,6.04,10.05,9]dec-3-yl)-4-
oxovalerate
Chemical Abstracts name ethyl 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-2-hydroxy-
-oxo-1,3,4-metheno-1H-cyclobuta[cd]pentalene-2-pentanoate CASRN[4234791]
DevelopmentcodesGC-9160 (Allied) SmilescodeCCOC(=O)CCC(=O)CC1(O)
C2(Cl)C3(Cl)C4(Cl)C1(Cl)C5(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C45Cl
kelevan 345
PHYSICAL CHEMISTRY:
Mol. wt. 634.8 M.f. C17H12Cl10O4
COMMERCIALISATION:
History Insecticide reported by E. E. Gilbert etal. (J. Agric. Food Chem., 1966, 14, 111);
development reviewed by H. Maier-Bode (Residue Rev., 1976, 63, 45). Invented by the Allied
Chemical Corp. and developed by C. F. Spiess & Sohn.
APPLICATIONS:
ModeofactionIngested insecticide. Uses Used to control Leptinotarsa decemlineata on
potatoes, Meligethes aeneus and Ceutorhynchus spp. (E. E. Gilbert et al., J. Agric. Food Chem.,
1966, 14, 111; H. Maier-Bode, Residue Rev., 1976, 63, 45). Formulation types WP.
PRODUCTS:
Discontinued products Despirol* (Spiess); Discontinuedmixtures Despirol Plus*
(+mancozeb) (Spiess).
ANALYSIS:
Residues determined by glc after oxidation to chlordecone (A. Westlake et al., J. Agric. Food
Chem., 1970, 18, 159).
EHC 66 (1986). HSG 2 (1987). EU Status (1107/2009) Never notified to the EU.
Oral Acute oral LD50 depends critically on the carrier used; for male rats 290->4000,
female rats 2402830, male rabbits 251 mg/kg. NOEL (90 d) for dogs 20100 mg/kg diet.
Toxicity Class WHO (a.i.) O ECClassification T; R24| Xn; R22| N; R51, R53
ENVIRONMENTAL FATE:
EHC 66 concluded that kelevan should not be used unless indispensable.
KH-502
Insecticide
S
P(OCH2CH3)2
N O
N
CF3
NOMENCLATURE:
IUPACname O,O-diethyl O-(1-phenyl-3-trifluoromethyl-1H-pyrazol-5-yl)
phosphorothioate
Chemical Abstracts name O-[1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl] O,O-diethyl
phosphorothioate Other names flupyrazofos (BSI rejected name)
346 KH-502
CASRN[122431247] DevelopmentcodesKH-502
PHYSICAL CHEMISTRY: Mol. wt. 380.3 M.f. C14H16F3N2O3PS
COMMERCIALISATION:
History Insecticide, discovered by KRICT and developed by Sungbo Chemicals Co. Ltd.
Registered in S Korea in 1996.
APPLICATIONS:
Biochemistry Acetylcholinesterase inhibitor. Uses For use against brown plant hopper,
green peach aphid and diamond-back moth, on Chinese cabbage.
PRODUCTS:
Discontinued products SunBong* (Sungbo).
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 (aerobic) 13.6 d (J-H. Kim et al., Pestic. Sci. (1998) 54 (3) 237).
leptophos
Insecticide
IRAC1B
NOMENCLATURE:
Common name leptophos (BSI, E-ISO, (m) F-ISO, ANSI, ESA); MBCP (JMAF)
IUPACname O-4-bromo-2,5-dichlorophenyl O-methyl phenylphosphonothioate
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl) O-methyl
phenylphosphonothioate CASRN[21609905] ECno2444728
DevelopmentcodesVCS 506 (Velsicol) SmilescodeCOP(=S)(Oc1cc(Cl)c(Br)cc1Cl)
c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 412.1 M.f. C13H10BrCl2O2PS Form Colourless
amorphous solid. M.p.70.270.6C S.g./density 1.53 (25C) Solubility In water 2.4
mg/l (25C). In acetone 470, benzene 1300, cyclohexane 142, heptane 59, isopropanol 24
(all in g/l, 25C). Stability Stable to acids for prolonged exposure at normal temperature,
but is slowly hydrolysed by alkali.
COMMERCIALISATION:
History Insecticide reported by A. K. Azab (Proc. Br. Insectic. Fungic. Conf., 5th, 1969, 2, 550).
Introduced by Velsicol Chemical Corp. Patents US 3459836
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic insecticide.
Uses The EC is effective against Lepidoptera, e.g. Spodoptera littoralis on cotton at 1.5
kg/ha; also on fruit and vegetables at 100 g/100 l. The GR, at 1.5 kg/ha, controls Ostrinia
nubilalis on maize. Formulation types DP; EC; GR; WP.
PRODUCTS:
Discontinued products Abar* (Velsicol); Phosvel* (Velsicol).
leptophos 347
ANALYSIS:
Product analysis by i.r. spectrometry or by glc. Residues determined by glc with FPD or
TID.
PDS 38 (1979).
Oral Acute oral LD50 for male albino ratsc.50 mg/kg. Phosphonate analogue: 105133
mg/kg. Skin and eye Acute percutaneous LD50 for albino rabbits >800 mg/kg. NOEL In
90 d feeding trials, no ill-effect was observed in rats receiving 10 mg/kg diet or dogs 30
mg/kg diet. ADI/RfD (JMPR) Temporary ADI withdrawn [1978]. Other Causes delayed
neurotoxicity. Toxicity Class WHO (a.i.) Ia ECClassification T; R25, R39/25| Xn; R21|
N; R50, R53
lirimfos
Insecticide
IRAC1B
NOMENCLATURE:
Common name lirimfos (BSI, E-ISO, (m) F-ISO)
IUPACname O-6-ethoxy-2-isopropylpyrimidin-4-yl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-[6-ethoxy-2-(1-methylethyl)-4-pyrimidinyl] O,O-
dimethyl phosphorothioate CASRN[38260638] DevelopmentcodesSAN 201I
SmilescodeCCOc1cc(OP(=S)(OC)OC)nc(n1)C(C)C
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG.
APPLICATIONS:
LS830556
Herbicide
CH3
O
S CH2 NH O
O
N C CH2 P OH
CH3 O OH
NOMENCLATURE:
IUPACname ({[mesyl(methyl)carbamoyl]methyl}amino)methylphosphonic acid
348 LS830556
Chemical Abstracts name [[[2-methyl(methylsulfonyl)amino]-2-oxoethyl]amino]

methylphosphonic acid Other names phosametine (withdrawn BSI proposed
name) CASRN[98565185] DevelopmentcodesLS830 556 (Rhne-Poulenc)
SmilescodeCN(C(=O)CNCP(=O)(O)O)S(=O)(=O)C
PHYSICAL CHEMISTRY: Mol. wt. 260.2 M.f. C5H13N2O6PS Form Crystals.
M.p.213215C V.p. <0.267 mPa Solubility In water 45 g/l (20C). In acetic acid 20 g/l.
Stability Stable at pH <4.
COMMERCIALISATION:
History Herbicide introduced by Rhne-Poulenc Agrochimie. Patents FR 2549839
APPLICATIONS: Uses Control of grass and broad-leaved weeds in vines, orchards and
cereals. Formulation types WG .
rabbits >4000 mg/kg.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail >2150 mg/kg. Fish LC50 (96 h) for rainbow trout
320 mg/l.
lythidathion
Insecticide
IRAC1B
NOMENCLATURE:
Common name lythidathion (BSI, E-ISO, (m) F-ISO)
IUPACname S-5-ethoxy-2,3-dihydro-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl
phosphorodithioate; 3-dimethoxyphosphinothioylthiomethyl-5-ethoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name S-[5-ethoxy-2-oxo-1,3,4-thiadiazol-3(2H)-ylmethyl] O,O-
dimethyl phosphorodithioate CASRN[2669321] DevelopmentcodesGS 12 968
(Ciba-Geigy); NC 2962 (FBC) SmilescodeCCOc1nn(CSP(=S)(OC)OC)c(=O)s1
COMMERCIALISATION:
History Insecticide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
lythidathion 349
malonoben
Acaricide
NOMENCLATURE:
Common name malonoben (BSI, E-ISO, ANSI, ESA); malonob(ne) ((m) F-ISO)
IUPACname 2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malononitrile
Chemical Abstracts name [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]
propanedinitrile CASRN[10537470] DevelopmentcodesGCP-5126; S 15126 (both
Gulf) SmilescodeCC(C)(C)c1cc(C=C(C#N)C#N)cc(c1O)C(C)(C)C
PHYSICAL CHEMISTRY: Mol. wt. 282.4 M.f. C18H22N2O Form Crystalline solid.
M.p.140141C
COMMERCIALISATION:
History Acaricide reported by H. Fukashi etal. (Agric. Biol. Chem., 1971, 35, 2003). Evaluated
by Gulf Oil Chemicals Co.
APPLICATIONS:
Biochemistry Uncouples respiratory phosphorylation (S. Muraoka & H. Terada, Biochim.
Biophys. Acta, 1972, 275, 271). ModeofactionIngested and contact acaricide.
Uses Effective against various mite species (Aculus, Brevipalpus, Eotetranychus,
Panonychus, Phyllocoptruta and Tetranychus) on beans, citrus, cotton, pome and stone fruit,
nut trees and ornamentals. Formulation types EC; SC. WP.
PRODUCTS:
Discontinued products GCP 51262 EC* (Gulf); GCP 512650 W* (Gulf); GPC 51264
L* (Gulf).
Oral Acute oral LD50 for rats 87 mg tech./kg. Skin and eye Acute percutaneous LD50 for
rabbits 2000 mg/kg. Toxicity Class WHO (a.i.) O
mancopper
Fungicide
multi-site: alkylenebis(dithiocarbamate)
NOMENCLATURE:
Common name mancopper (BSI, E-ISO, F-ISO)
IUPACname ethylenebis(dithiocarbamate) mixed metal complex containingc.13.7%
manganese andc.4% copper
Chemical Abstracts name [[1,2-ethanediylbis[carbamodithioato]](2-)]manganese
mixture with [[1,2-ethanediylbis[carbamodithioato]](2-)]copper CASRN[53988935]
COMMERCIALISATION:
History Fungicide introduced by Rohm & Haas Co. (now Dow AgroSciences).
350 mancopper
APPLICATIONS:
Biochemistry Non-specific thiol reactant, inhibiting respiration.
ModeofactionFungicide with protective action. Uses Control of downy mildew on
vines. Also used as a seed treatment for control of Septoria and Fusarium spp. on cereals.
Formulation types WP; Seed treatment.
PRODUCTS:
Discontinued products Dithane C-90* (Dow AgroSciences).
ANALYSIS:
Details from Dow AgroSciences.
EHC 78 (1988) is a general review of dithiocarbamates and their degradation products.
EHC 200 (1998) is a general review of copper and copper compounds. JMPR Mtg. 68
(1993); JMPR Evaln. I 69 (1993); JMPR Evaln. II 70 (1993) for ethylenethiourea.
Oral Acute oral LD50 for rats 9600 mg/kg.
mazidox
Insecticide
IRAC1B
NOMENCLATURE:
Common name mazidox (BSI, E-ISO, (m) F-ISO)
IUPACname tetramethylphosphorodiamidic azide (I); tetramethylazidophosphonic
diamide
Chemical Abstracts name (I) CASRN[7219785] DevelopmentcodesNC 7
SmilescodeCN(C)P(=O)(N=[N+]=[N-])N(C)C
PHYSICAL CHEMISTRY: Mol. wt. 177.1 M.f. C4H12N5OP
COMMERCIALISATION:
History Insecticide evaluated by Pest Control Ltd (became Schering Agrochemicals).
APPLICATIONS:
mebenil
Fungicide
NOMENCLATURE:
Common name mebenil (BSI, E-ISO, (m) F-ISO)
IUPACname o-toluanilide
mebenil 351
Chemical Abstracts name 2-methyl-N-phenylbenzamide

CASRN[7055030] DevelopmentcodesBAS 305F; BAS 3050F; BAS 3053F (all
BASF) SmilescodeCc1ccccc1C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 211.3 M.f. C14H13NO Form Crystalline solid.
M.p.125C V.p. 4.4 103 mPa (20C) Solubility Soluble in most organic solvents, e.g.
acetone, DMF, DMSO, ethanol, methanol, 3,5,5-trimethylcyclohex-2-enone.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer and J. Kradel (Proc. Br. Insectic. Fungic. Conf.,
5th, 1969, 2, 563). Developed by BASF AG.
APPLICATIONS: Uses Effective against Basidiomycetes and for the control of Puccinia
spp. on cereals at 1.72.5 kg/ha, and for treating seed potatoes against Rhizoctonia spp. at
0.300.37 g/kg seed. Formulation types Seed treatment; WP.
Oral Acute oral LD50 for rats 6000 mg/kg. Skin and eye Not a skin irritant.
mecarbinzid
Fungicide
NOMENCLATURE:
Common name mecarbinzide (BSI before 1984, (m) F-ISO); mecarbinzid (BSI from 1984,
E-ISO)
IUPACname methyl 1-(2-methylthioethylcarbamoyl)benzimidazol-2-ylcarbamate
Chemical Abstracts name methyl 1-[[[2-(methylthio)ethyl]amino]carbonyl]-1H-
benzimidazol-2-ylcarbamate CASRN[27386647] DevelopmentcodesBAS 3201F
(BASF) SmilescodeCOC(=O)Nc1nc2ccccc2n1C(=O)NCCSC
COMMERCIALISATION:
History Fungicide evaluated by BASF AG.
APPLICATIONS:
ModeofactionSystemic fungicide.
352 mecarbinzid
mecarphon
Insecticide
IRAC1B
NOMENCLATURE:
Common name mecarphon (BSI, E-ISO, (m) F-ISO)
IUPACname methyl [methoxy(methyl)phosphinothioylthio]acetyl(methyl)carbamate;
S-(N-methoxycarbonyl-N-methylcarbamoylmethyl) O-methyl methylphosphonodithioate
Chemical Abstracts name methyl 3,7-dimethyl-6-oxo-2-oxa-4-thia-7-aza-3-
phosphaoctan-8-oate 3-sulfide; methyl [[methoxy(methylphosphinothioyl)thio]acetyl]
methylcarbamate (former 9CI) CASRN[29173317] DevelopmentcodesMC 2420
SmilescodeCOC(=O)N(C)C(=O)CSP(=S)(C)OC
PHYSICAL CHEMISTRY: Mol. wt. 271.3 M.f. C7H14NO4PS2 Form Colourless solid.
M.p.36C Solubility In water 300 mg/l (20C). Soluble in aromatic hydrocarbons,
chlorinated hydrocarbons, ethanol; insoluble in hexane.
COMMERCIALISATION:
History Insecticide reported by M. Pianka & W. S. Catling (Proc. Int. Congr. Entomol., 13th,
Moscow, 1968, 2, 263). Introduced by Murphy Chemical Co. (later DowElanco).
Patents GB 1268199
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact insecticide.
Uses Effective at 500 mg/l against Hemiptera, including scale insects, Drosophila spp. on
pome and stone fruit, citrus and olives. Formulation types EC; WP.
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD.
720 mg/kg. Toxicity Class WHO (a.i.) O
medinoterb acetate; medinoterb

Herbicide
NOMENCLATURE:
Common name medinoterb (BSI, E-ISO); m(dinoterbe) ((m) F-ISO)
IUPACname 6-tert-butyl-2,4-dinitro-m-cresol; 6-tert-butyl-3-methyl-2,4-dinitrophenol
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-methyl-2,4-dinitrophenol
CASRN[3996596] medinoterb; [2487016] medinoterb acetate ECno2196346
acetate DevelopmentcodesP 1488; MC 1488 (both for the acetate)
medinoterb acetate; medinoterb 353

PHYSICAL CHEMISTRY:
Mol. wt. 254.2; (acetate 296.3) M.f. C11H14N2O5; (acetate C13H16N2O6)
Form Medinoterb acetate is a yellow crystalline solid. M.p.8687C (acetate) V.p. 53
mPa (40C) (acetate) Solubility In water <10 mg/l (room temperature, acetate). The
acetate is slightly soluble in hexane; very soluble in acetone, xylene. Stability The acetate
is stable, though slowly hydrolysed by alkali (room temperature) and rapidly on heating.
COMMERCIALISATION:
History Herbicide reported by G. A. Emery etal. (Proc. 2nd EWRC Symp. New Herbic.,
1965, p. 141). Introduced by Murphy Chemical Co. (later DowElanco).
Patents GB 1080282
APPLICATIONS: Uses Medinoterb acetate is toxic to seedlings and was recommended
pre-em. at 0.561.1 kg/ha on sugar beet; also on cotton and leguminous crops.
ANALYSIS:
Product analysis by reduction of the nitro groups by titanium(II) sulfate. Residues
determined by colorimetry as medinoterb.
Oral Medinoterb acetate: Acute oral LD50 for rats 42, rabbits 80 mg/kg.
Skin and eye Medinoterb acetate: Acute percutaneous LD50 for rats 1300, guinea-pigs
>200 mg/kg. NOEL Medinoterb acetate: (90 d) for male rats 1 mg/kg daily, for female
rats 1.2 mg/kg daily. Toxicity Class WHO (a.i.) O ECClassification T; R25| Xn; R21
(acetate)
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 560 mg/kg (medinoterb acetate).
ENVIRONMENTAL FATE:
Soil/Environment Decomposed in soil in 120 d.
menazon
Insecticide
IRAC1B
NOMENCLATURE:
Common name menazon (BSI, E-ISO, F-ISO, JMAF, ESA); azidithion (France)
IUPACname S-4,6-diamino-1,3,5-triazin-2-ylmethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[(4,6-diamino-1,3,5-triazin-2-yl)methyl] O,O-dimethyl
phosphorodithioate CASRN[78579] ECno2011234 DevelopmentcodesPP175
(ICI) SmilescodeCOP(=S)(OC)SCc1nc(N)nc(N)n1
PHYSICAL CHEMISTRY:
Composition Tech. is 9095%. Mol. wt. 281.3 M.f. C6H12N5O2PS2 Form Colourless,
354 menazon
odourless crystals; (tech. has a mercaptan-like odour). It forms a crystalline hydrochloride.

M.p.160162C (decomp.) V.p. 0.13 mPa (25C) Solubility In water 240 mg/l (20C).
In 2-ethoxyethanol 200, 2-methoxyethanol 250, tetrahydrofurfuryl alcohol 150, ethylene
glycol 100 (all in g/kg, room temperature). Stability The solid is stable 50C, but is
unstable under acid (pH <4) or alkaline (pH >8) conditions.
COMMERCIALISATION:
History Insecticide reported by A. Calderbank (Chem. Ind. (London), 1961, p. 630).
Introduced by ICI Plant Protection Division (later ICI Agrochemicals). Patents GB 899701
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide.
Uses Mainly as a tuber or seed treatment to protect seedlings, for foliage application, as
a soil drench and root dip. Formulation types SC. WP. Compatibility Not compatible
with strongly alkaline pesticides, and may be decomposed by the reactive surfaces of some
inert fillers.
PRODUCTS:
Discontinued products Saphicol* (ICI); Saphizon* (ICI); Sayfos* (ICI);
Discontinuedmixtures Abol X* (+gamma-HCH) (ICI).
ANALYSIS:
Product analysis by oxidation to phosphoric acid, estimated by colorimetry. Residues
determined after conversion to phosphoric acid and subsequent colorimetry (A.
Calderbank & J. B. Turner, Analyst (London), 1962, 87, 273; A. Calderbank, Anal. Methods Pestic.
Plant Growth Regul., 1973, 7, 317).
Oral Acute oral LD50 for female rats 1950 mg/kg. Skin and eye Rabbits treated on their
shaved backs for 24 h with 500800 mg/kg suffered no local or systemic toxic effect.
NOEL (90 d) for rats 30 mg/kg diet; in a 2 y trial, rats receiving 4000, 1000 or 250 mg/kg
diet showed no significant effect other than partial inhibition of cholinesterase.
Toxicity Class WHO (a.i.) III ECClassification Xn; R22| N; R52, R53
menazon 355
mephosfolan
O
P(OCH2CH3)2
N
S
S
IRAC1B CH3
NOMENCLATURE:
Common name mephosfolan (BSI, E-ISO); m(phospholan) ((m) F-ISO)
IUPACname diethyl 4-methyl-1,3-dithiolan-2-ylidenephosphoramidate;
2-(diethoxyphosphinylimino)-4-methyl-1,3-dithiolane
Chemical Abstracts name diethyl (4-methyl-1,3-dithiolan-2-ylidene)phosphoramidate
CASRN[950107] ECno2134473 DevelopmentcodesEI 47 470 (Cyanamid)
SmilescodeCCOP(=O)(OCC)N=C1SCC(C)S1
PHYSICAL CHEMISTRY: Mol. wt. 269.3 M.f. C8H16NO3PS2 Form Yellow to amber
liquid (tech.). B.p. 120C /0.001 mmHg Kow logP = 1.045 Solubility In water 57 mg/l
(25C). Soluble in ethanol, acetone, 1,2-dichloroethane, and benzene. Stability Stable in
aqueous solution under neutral conditions. Hydrolysed by acids and alkalis 2>pH>9.
COMMERCIALISATION:
History Insecticide and acaricide introduced by American Cyanamid Co.
Patents GB 974138 Manufacturers Cyanamid
APPLICATIONS:
acaricide with contact and stomach action. Absorbed by the roots and leaves.
Uses Control of aphids, thrips, bollWorms, jassids, mites, stem borers, whitefly, and leaf-
eating larvae on cotton, fruit, hops, maize, sorghum, rice, sugar cane, potatoes, vegetables,
tobacco, etc. Phytotoxicity Cotton foliage may be injured in high-rainfall conditions.
Formulation types EC; GR .
PRODUCTS:
Discontinued products Cytro-Lane* (Cyanamid).
ANALYSIS:
Product analysis by uv spectroscopy. Residues determined by glc (N. R. Pasarela & E. J.
Orloski, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 231; R. C. Blinn & J. E. Boyd, J. Assoc.
Off. Agric. Chem., 1964, 47, 1106).
EHC 63 (1986), a general review of organophosphorus insecticides. EU Status
356 mephosfolan
Oral Acute oral LD50 for rats 3.98.9 mg tech./kg; for albino mice 11.3 mg/kg.
Skin and eye Acute percutaneous LD50 (24 h) for male albino rabbits 28.7 mg tech./
kg, >5000 mg (as 2% GR)/kg. NOEL In 90 d feeding trials, male albino rats receiving 15
mg/kg diet showed a reduction in erythrocyte and brain cholinesterase activity, but there
was no significant effect on weight gain. Toxicity Class WHO (a.i.) Ia EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 12.8 mg/kg. Fish LC50 (96 h) for rainbow trout
2.1, carp 54.5 mg/l. Bees Toxic to bees; LC50 (topical) 3.5 g/bee.
mercuric oxide
Fungicide, wound protectant
HgO
NOMENCLATURE:
Common name oxyde mercurique (F-ISO, accepted in lieu of a common name);
mercuric oxide (E-ISO, accepted in lieu of a common name)
IUPACname mercury(II) oxide; mercury oxide
Chemical Abstracts name mercury oxide (HgO) Other names yellow oxide of
mercury CASRN[21908532], formerly [1344452] SmilescodeO=[Hg]
PHYSICAL CHEMISTRY:
Mol. wt. 216.6 M.f. HgO Form Orange-red to bright red powder (yellow when finely
divided). M.p.Decomposes atc.500C Solubility In water 53 mg/l (25C). Insoluble in
organic solvents. Soluble in dilute acids, forming the corresponding mercury salts. Stability
Decomposes on exposure to light. Darkens atc.400C and decomposes into mercury and
oxygen atc.500C.
COMMERCIALISATION:
History Introduced by Sandoz AG (became Novartis Crop Protection AG, who ceased to
manufacture or market it).
APPLICATIONS: Uses Wound protectant for pruning cuts and other bark injuries,
and control of canker, on fruit trees, rubber trees, vines, and ornamental trees and shrubs.
Formulation types PA .
PRODUCTS:
Discontinued products Kankerdood* (Bayer); Kankertox* (Ciba); Santar* (Sandoz,
Zeneca).
ANALYSIS:
Product analysis by colorimetry (CIPACHandbook, 1970, 1, 514), by titration (AOACMethods,
18th Ed., 971.04) or by gravimetry (ibid., 922.05). Mercury impurities determined
mercuric oxide 357

(CIPACHandbook, 1994, F, 264).

ICSC.981 (2001). CICAD 50 (2003). IARC 58 (1994). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EEC as amended by
91/188/EEC.
IARC Class 3
Oral Acute oral LD50 for rats 18 mg/kg. Extremely poisonous orally to all animals.
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassification Not specified, but
inorganic mercury generally is assigned T+; R26/27/28| R33| N; R50, R53, concentration-
dependent. PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fish.
mercurous chloride
H
g 2C
l 2
NOMENCLATURE:
Common name chlorure mercureux (F-ISO, accepted in lieu of a common name);
mercurous chloride (E-ISO, accepted in lieu of a common name)
IUPACname mercury(I) chloride; dimercury dichloride
Chemical Abstracts name mercury chloride (Hg2Cl2) Other names
calomel CASRN[10112911] Hg2Cl2; [7546307] HgCl ECno2333075
SmilescodeCl[Hg][Hg]Cl
PHYSICAL CHEMISTRY:
Mol. wt. 472.1 M.f. Cl2Hg2 Form White powder. M.p.Sublimes at 400500C
S.g./density 7.15 Solubility In water 2 mg/l (25C). Soluble in most organic solvents,
and also in cold dilute acids. Stability Decomposes slowly in sunlight. Under aqueous
conditions, slowly decomposes to mercury and mercuric chloride (more rapid
decomposition in the presence of alkali).
COMMERCIALISATION:
History Has long been used as an insecticide and, having a lower toxicity to mammals,
largely replaced mercuric chloride, as recommended by H. Glasgow (J. Econ. Entomol., 1929,
22, 335).
APPLICATIONS: Uses Soil application for control of Delia spp. and Plasmodiophora
brassicae in brassicas; and Sclerotium cepivorum in onions. Control of dollar spot and
Fusarium patch on turf. Phytotoxicity Phytotoxic to many crops.
Formulation types DP; TC.
358 mercurous chloride

PRODUCTS:
Discontinued products Cyclosan* (Rhne-Poulenc).
ANALYSIS:
Product analysis by colorimetry (CIPACHandbook, 1970, 1, 514), by titration
(AOACMethods, 18th Ed., 971.04) or by gravimetry (ibid., 922.05). Mercury impurities
determined (CIPACHandbook, 1994, F, 264). Residues determined by atomic absorption
spectrophotometry (AOACMethods, 14th Ed., 25.13125.135) or by colorimetry (ibid.,
25.13825.145).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. ICSC.984
(2000). CICAD 50 (2003). EU Status (1107/2009) Considered to be outside the scope of
the Directive; already banned, 79/117/EEC as amended by 91/188/EEC.
IARC Class Inorganic mercury compounds classified 3
Oral Acute oral LD50 for rats 210 mg/kg. Toxicity Class WHO (a.i.) II EPA (formulation)
II ECClassification Xn; R22| Xi; R36/37/38| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fish.
mesoprazine
Herbicide
NOMENCLATURE:
Common name mesoprazine (BSI, E-ISO, (f) F-ISO)
IUPACname 6-chloro-N2-isopropyl-N4-(3-methoxypropyl)-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N-(3-methoxypropyl)-N-(1-methylethyl)-1,3,5-
triazine-2,4-diamine CASRN[1824095] DevelopmentcodesG 34 698; CGA 4999
SmilescodeCOCCCNc1nc(Cl)nc(NC(C)C)n1
COMMERCIALISATION:
mesoprazine 359
mesulfenfos
Insecticide
O
S
O
O
P
O
S
IRAC1B O,O-dimethyl O-4-methylsulfinyl-m-tolyl phosphorothioate
NOMENCLATURE:
Common name m(sulfenfos) ((m) F-ISO); mesulfenfos (BSI, E-ISO)
IUPACname O,O-dimethyl O-4-methylsulfinyl-m-tolyl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-[3-methyl-4-(methylsulfinyl)phenyl]
phosphorothioate CASRN[3761419] DevelopmentcodesBAY S 2281
SmilescodeCOP(=S)(OC)Oc1ccc(S(=O)C)c(C)c1
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Baycid SO* (Bayer).
metamifop
Herbicide
F
O
Cl O
N N
CH3 CH3
O O
NOMENCLATURE:
Common name m(tamifop) ((m) F-ISO); metamifop (BSI, E-ISO)
IUPACname (R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]-2-fluoro-N-
methylpropionanilide
Chemical Abstracts name (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]
phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide CASRN[256412
892] DevelopmentcodesDBH-129; K-12974 (both Dongbu Hannong)
360 metamifop
SmilescodeC[C@@H](Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1)C(=O)N(C)
c4ccccc4F;without stereochemistry:CC(Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1)C(=O)N(C)
c4ccccc4F
PHYSICAL CHEMISTRY:
Composition 96%. Mol. wt. 440.9 M.f. C23H18ClFN2O4 Form Light brown, odourless,
fine granular powder. M.p.77.078.5C B.p. Decomposes V.p. 1.51 101 mPa (25C)
Kow logP = 5.45 (pH 7, 20C) Henry 6.35 10-2 Pa m3 mol1 (20C) S.g./density
1.39 Solubility In water 6.87 104 g/l (pH 7, 20C). In acetone, 1,2-dichloroethane,
ethyl acetate, methanol and xylene >250, n-heptane 2.32, n-octanol 41.9 (all in g/l, 20C).
Stability Stable at 54C.
COMMERCIALISATION:
History Reported by T. J. Kim etal. (Proc. BCPC Int. Congr., Glasgow, 2003, 1, 81).
Discovered by Korean Research Institute of Chemical Technology (KRICT) and developed
by Dongbu Hannong Chemical Co. Ltd (now Dongbu HiTek).
Manufacturers Dongbu HiTek
APPLICATIONS:
Biochemistry Acetyl-CoA carboxylase (ACCase) inhibitor. Rice/Echinochloa selectivity
is mainly due to differential sensitivity to ACCase, and may also be due to differential
foliar uptake. The (S)- isomer is less active than the (R)- isomer. ModeofactionCauses
chlorosis in developing leaves, with growth inhibition. Uses Post-emergence control
of annual and perennial grass weeds (including Echinochloa spp., Leptochloa chinensis,
Digitaria spp. and Eleusine indica) in various crops, including rice; applied at 90200 g/ha for
upland crops (wheat, soya beans, cotton, turf, etc.). Formulation types EC; GR; ME; WG .
PRODUCTS:
Other products Pizero (Dongbu HiTek).
EU Status (1107/2009) Never notified and authorised in the EU.
rats >2000 mg/kg. Not a skin irritant; slightly irritating to eyes. May cause sensitisation
by skin contact. Inhalation LC50 (4 h) for rats >2.61 mg/l. Other Non-mutagenic in the
Ames, chromosome aberration, cell mutation and micronucleus tests.
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout 0.307 mg/l. Daphnia EC50 (48 h) 0.288 mg/l.
Algae EC50 (48 h) >2.03 mg/l. Bees LD50 (contact and oral) >100 g/bee. Worms LC50
for earthworms >1000 ppm.
ENVIRONMENTAL FATE:
Soil/Environment Soil degradation is both chemical and microbial; DT50 4060 d (25C).
Aqueous photolysis produces seven detectable metabolites; DT50 18120 d, depending on
conditions.
metamifop 361
metazoxolon
Fungicide
NOMENCLATURE:
Common name metazoxolon (BSI, E-ISO, (m) F-ISO)
IUPACname 4-(3-chlorophenylhydrazono)-3-methyl-1,2-oxazol-5(4H)-one;
4-(3-chlorophenylhydrazono)-3-methylisoxazol-5(4H)-one
Chemical Abstracts name 3-methyl-4,5-isoxazoledione 4-[(3-chlorophenyl)hydrazone]
CASRN[5707733] DevelopmentcodesPP395
SmilescodeCC1=NOC(=O)C1=NNc2cccc(Cl)c2
COMMERCIALISATION:
History Fungicide reported by T. J. Purnell (Proc. Br. Crop Prot. Conf., 7th, 1973, 2, 603).
Evaluated by ICI Agrochemicals.
APPLICATIONS: Uses Control of Pythium spp. on ornamentals, peanuts and peas,
Rhizoctonia solani on cotton, Phytophthora capsici on peppers, Fusarium nivale on rye, and
Fusarium nivale on wheat, when applied as a seed or soil treatment.
Oral Acute oral LD50 for female rats 3340 mg/kg. Skin and eye Acute percutaneous LD50
for rats >1000 mg/kg Not a skin or eye irritant.
metflurazon
Herbicide
NOMENCLATURE:
Common name metflurazon (BSI (from 1984), E-ISO); metflurazone (BSI (before 1984),
(f) F-ISO)
IUPACname 4-chloro-5-dimethylamino-2-(,,-trifluoro-m-tolyl)pyridazin-3(2H)-one
Chemical Abstracts name 4-chloro-5-(dimethylamino)-2-[(3-trifluoromethyl)
phenyl]-3(2H)-pyridazinone CASRN[23576230] DevelopmentcodesSAN 6706H
SmilescodeCN(C)c1cnn(c2cccc(c2)C(F)(F)F)c(=O)c1Cl
PHYSICAL CHEMISTRY: Mol. wt. 317.7 M.f. C13H11ClF3N3O
COMMERCIALISATION:
History Herbicide evaluated by Sandoz AG.
362 metflurazon
methacrifos
S
CH3 P(OCH3)2
CH3O C O
C C
O H
IRAC1B
NOMENCLATURE:
Common name methacrifos (BSI, E-ISO, (m) F-ISO)
IUPACname methyl (E)-3-(dimethoxyphosphinothioyloxy)-2-methacrylate; (E)-O-2-
methoxycarbonylprop-1-enyl O,O-dimethyl phosphorothioate
Chemical Abstracts name (E)-methyl 3-[(dimethoxyphosphinothioyl)oxy]-2-methyl-2-
propenoate CASRN[62610779] (E)- isomer; [30864289] unstated stereochemistry
ECno2503662 DevelopmentcodesCGA 20 168 SmilescodeCOC(=O)
C(=COP(=S)(OC)OC)C
PHYSICAL CHEMISTRY:
Mol. wt. 240.2 M.f. C7H13O5PS Form Colourless liquid. B.p. 90C /0.01 mmHg
V.p. 160 mPa (20C) Kow logP 3.0 Henry 9.61 10-2 Pa m3 mol1 (calc.) S.g./density
1.225 (20C) Solubility In water 400 mg/l (20C). Miscible with many organic solvents,
e.g. methanol, benzene, hexane, and dichloromethane. Stability Relatively unstable in
alkaline conditions; on hydrolysis DT50 (calc.) (20C) 66 d (pH 1), 29 d (pH 7), 9.5 d (pH
9). Decomposes atc.200C. F.p. 6973C
COMMERCIALISATION:
History Insecticide reported by R. Wyniger etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1977,
3, 1033). Introduced by Ciba-Geigy AG (later Novartis Crop Protection AG).
Patents BE 766000; GB 1342630 Manufacturers Novartis
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide and acaricide
with respiratory, contact, and stomach action. Gives rapid knockdown, and has long
residual activity. Uses Mainly used for control of arthropod pests in stored products by
incorporation or by surface treatment. Phytotoxicity Should not be used on plant foliage.
Formulation types DP; EC. Compatibility Incompatible with strongly acidic or alkaline
materials.
PRODUCTS:
Discontinued products Damfin* (Novartis).
ANALYSIS:
Product analysis by glc. Residues in grain determined by glc with FPD or TID (J.
Desmarchelier et al., Pestic. Sci., 1977, 8, 473).
methacrifos 363

EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Mtg. 65 (1992);
JMPR Evaln. I 66 (1992); JMPR Evaln. II 61 (1990). EU Status (1107/2009) Not approved,
>3100 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). Inhalation LC50 (6 h) for
rats 2.2 mg/l air. NOEL (2 y) for rats 0.6 mg/kg b.w. daily. ADI/RfD (JMPR) 0.006 mg/kg
b.w. [1990]. Toxicity Class WHO (a.i.) II ECClassification Xn; R22| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 116 mg/kg. Fish LC50 (96 h) for carp 30.0,
rainbow trout 0.4 mg/l.
ENVIRONMENTAL FATE:
Animals Rapid excretion; metabolism via hydrolysis of the methyl esters as well as
cleavage of the phosphoric and vinyl ester bonds, followed by mineralisation to CO2.
methalpropalin
Herbicide
NOMENCLATURE:
Common name methalpropalin (BSI, E-ISO); m(thalpropaline) ((f) F-ISO)
IUPACname ,,-trifluoro-N-(2-methylallyl)-2,6-dinitro-N-propyl-p-toluidine
Chemical Abstracts name N-(2-methyl-2-propenyl)-2,6-dinitro-N-propyl-4-
(trifluoromethyl)benzenamine CASRN[57801464]
SmilescodeCCCN(CC(=C)C)c1c(cc(cc1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide evaluated by Eli Lilly & Co.
methanesulfonyl fluoride
Insecticide
NOMENCLATURE:
IUPACname methanesulfonyl fluoride (I)
Chemical Abstracts name (I) Other names MSF CASRN[558258]
SmilescodeCS(=O)(=O)F
PHYSICAL CHEMISTRY: Mol. wt. 98.10 M.f. CH3FO2S
COMMERCIALISATION:
History Fumigant insecticide marketed by Bayer AG.
364 methanesulfonyl fluoride

APPLICATIONS:
PRODUCTS:
Discontinued products Fumette* (Bayer).
methasulfocarb
Fungicide, plant growth regulator
CH3NHCOS OSO2CH3
FRAC42, U; thiocarbamate fungicide

NOMENCLATURE:
Common name m(thasulfocarb) ((m) F-ISO); methasulfocarb (BSI, E-ISO)
IUPACname S-4-methylsulfonyloxyphenyl methylthiocarbamate
Chemical Abstracts name S-[4-[(methylsulfonyl)oxy]phenyl] methylcarbamothioate
CASRN[66952496] DevelopmentcodesNK-191 (Nippon Kayaku)
SmilescodeCNC(=O)Sc1ccc(OS(=O)(=O)C)cc1
PHYSICAL CHEMISTRY: Mol. wt. 261.3 M.f. C9H11NO4S2 Form Colourless crystals.
M.p.137.5138.5C Solubility In water 480 mg/l. Soluble in acetone, alcohols, and
benzene. Stability Stable to light.
COMMERCIALISATION:
History Fungicide and plant growth regulator reported by K. Ohmori (Jpn. Pestic. Inf.,
1985, No. 46, p. 17). Introduced in Japan (1984) by Nippon Kayaku Co., Ltd.
Patents US 4126696; DE 2745229; JP 5347527 Manufacturers Nippon Kayaku
APPLICATIONS: Uses Soil fungicide for control of Corticium, Fusarium, Mucor,
Pseudomonas, Pythium, Rhizopus, Rhizoctonia, and Trichoderma spp. in rice. Application rate
0.61 g/rice nursery tray. Formulation types DP .
PRODUCTS:
Discontinued products Kayabest* (Nippon Kayaku).
ANALYSIS:
Product and residue analysis by glc.
Skin and eye Acute percutaneous LD50 for rats and mice >5000 mg/kg. Inhalation LC50
(4 h) for rats >0.44 mg/l air. Other Non-mutagenic to mice. Non-teratogenic to rats.
ECOTOXICOLOGY:
methasulfocarb 365
methazole
Herbicide
O
CH3
N
Cl N
O O
Cl
NOMENCLATURE:
Common name methazole (BSI, ANSI, Australia, WSSA)
IUPACname 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione
Chemical Abstracts name 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-
3,5-dione CASRN[20354261] ECno2437616 DevelopmentcodesVCS-438
(Sandoz) SmilescodeCn1c(=O)on(c2ccc(Cl)c(Cl)c2)c1=O
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 261.1 M.f. C9H6Cl2N2O3 Form Colourless crystals;
(tech. a light tan solid). M.p.123124C V.p. 0.133 mPa (25C) Kow logP = 2.590.04
(25C) Henry 2.32 10-2 Pa m3 mol1 (calc.) S.g./density 1.24 (25C) Solubility In
water 1.5 mg/l (25C). In DMF 323, dichloromethane 255, cyclohexanone 171, acetone
40, xylene 55, methanol 6.5 (all in g/l, 25C). Stability Solutions in methanol undergo
photodecomposition when exposed to uv light. Suspensions in water, when exposed to
sunlight, are more stable (G. W. Ivie et al., J. Agric. Food Chem., 1973, 21, 386). Hydrolysed in
strongly acidic and alkaline media. Decomposes below the b.p.
COMMERCIALISATION:
History Herbicide reported by W. Furness (Proc. Int. Congr. Plant Prot., 7th, Paris, 1970,
p. 314). Introduced by Velsicol Chemical Corp. and later manufactured and marketed by
Sandoz AG. Patents US 3437664
APPLICATIONS:
ModeofactionSelective systemic herbicide, absorbed by the roots and leaves, with
translocation. Uses Used to control certain grasses and many broad-leaved weeds: pre-
emergence in garlic and potatoes (12 kg/ha); as a directed spray on to soil or emerged
weeds in citrus, stone-fruit, nuts, tea and established vines (6 kg/ha) and on cotton 15 cm
tall (12 kg/ha), onions (>2 leaves) (2.5 kg/ha), newly seeded or winter-dormant alfalfa
(>1 y old) (2.25 kg/ha). Preferably applied to moist soil; lower rates were applicable to light
sandy soils. Formulation types WP; GR; WG . Compatibility Incompatible with some
ester-type hormone herbicides.
PRODUCTS:
Discontinued products Probe* (Sandoz); Tunic* (Sandoz).
ANALYSIS:
Product analysis by lc and i.r. spectrophotometry (AOACMethods, 18th Ed., 992.02, 982.03;
366 methazole
D. M. Whiteacre et al., Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 367). Residues
determined by glc with ECD (idem, ibid.) or by hplc (idem, ibid.).
for rabbits >12500 mg/kg. Mild irritant to skin and eyes (rabbits). No skin sensitisation
(guinea pigs). Chloracne observed in rabbit-ear studies and among certain workers at
manufacturing plants. Inhalation LC50 (4 h) for rats >200 mg/l air (dust). NOEL In 2-year
feeding trials in rats and mice, a yellow-brown pigment occurred in the spleen or liver at
>100 mg/kg diet. Non-mutagenic and non-teratogenic in rabbits (at up to 60 mg/kg daily),
but foetal toxicity observed at 30 mg/kg daily. In a 3-generation study in rats, NOEL
was 50 mg/kg diet (cataracts were observed at 100 mg/kg diet, but no other ill-effects).
Toxicity Class WHO (a.i.) III ECClassification Xn; R21/22| Xi; R36/38| N; R51, R53
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks 11200, bobwhite quail 1825 mg/kg diet. In
1-generation study NOEL for bobwhite quail and mallard ducks 3 mg/kg diet. Fish LC50
(96 h) for bluegill sunfish 4.47, rainbow trout 4.09 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, methazole undergoes decarboxylation to 1-(3,4-dichlorophenyl)-3-
methylurea, which is further degraded by N-demethylation to 3,4-dichlorophenylurea, and
then to 3,4-dichloroaniline. Degradation is almost complete within 3 d.
Soil/Environment Microbially degraded in soil by the same route as in plants. Soil DT50
<30 d.
methfuroxam
Fungicide
NOMENCLATURE:
Common name methfuroxam (BSI, E-ISO, ANSI); m(thfuroxame) ((m) F-ISO)
IUPACname 2,4,5-trimethyl-3-furanilide
Chemical Abstracts name 2,4,5-trimethyl-N-phenyl-3-furancarboxamide
CASRN[28730178] DevelopmentcodesH719 (Uniroyal)
SmilescodeCc1oc(C)c(C(=O)Nc2ccccc2)c1C
PHYSICAL CHEMISTRY: Mol. wt. 229.3 M.f. C14H15NO2 Form Colourless crystals
with a faint odour. M.p.138142C V.p. <13 Pa (20C) Solubility In water
10 mg/l (25C). In DMF 412, acetone 125, methanol 64, benzene 36 (all in g/kg).
Stability Hydrolysed by strong acids and alkalis.
methfuroxam 367
COMMERCIALISATION:
History Fungicide reported by K. T. Alcock (Plant Dis. Reptr., 1978, 62, 854). Introduced in
Germany by Uniroyal Chemical Co., Inc. Patents DE 2006471
APPLICATIONS:
Biochemistry Inhibitor of succinate dehydrogenase complex, in the respiratory electron
transport chain. ModeofactionSystemic fungicide. Uses Seed treatment for control of
Tilletia and Ustilago spp. in cereals applied at up to 50 g/100 kg seed.
Formulation types DS; FS; LS; WS .
PRODUCTS:
Discontinued products Trivax* (Uniroyal).
ANALYSIS:
Product analysis by gc.
Oral Acute oral LD50 for male rats 4300, female rats 1470, mice 620880, dogs 10000
mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 3160 mg/kg. No skin irritation
(rabbits); slight irritation of mucous membranes. Inhalation LC50 for rats 17.39 mg/l air.
NOEL In 90 d feeding trials, no ill-effects were observed in rats at 300 mg/kg diet or in
dogs at 1000 mg/kg diet.
ECOTOXICOLOGY:
Fish LC50 for bluegill sunfish 0.18, rainbow trout 0.26 mg/l. Bees Combinations with
imazalil and thiabendazole are not hazardous to bees when used as recommended.
ENVIRONMENTAL FATE:
Plants After application of 30 g methfuroxam per 100 kg seed, the residue levels in unripe
and ripe maize are 0.020.13 and 00.01 mg/kg, respectively.
methiobencarb
Herbicide
NOMENCLATURE:
Common name methiobencarb (BSI, E-ISO); m(thiobencarbe) ((m) F-ISO)
IUPACname S-4-methoxybenzyl diethylthiocarbamate
Chemical Abstracts name S-[(4-methoxyphenyl)methyl] diethylcarbamothioate
CASRN[18357783] DevelopmentcodesNTN 5810
SmilescodeCCN(CC)C(=O)SCc1ccc(OC)cc1
COMMERCIALISATION:
368 methiobencarb
methiuron
Herbicide
NOMENCLATURE:
Common name methiuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1,1-dimethyl-3-m-tolyl-2-thiourea
Chemical Abstracts name N,N-dimethyl-N-(3-methylphenyl)thiourea
CASRN[21540352] DevelopmentcodesMH 090
SmilescodeCN(C)C(=S)Nc1cccc(C)c1
PHYSICAL CHEMISTRY: Mol. wt. 194.3 M.f. C10H14N2S Form Colourless crystals.
M.p.145C Solubility In water 400 mg/l (25C). In methanol 70, pyridine 470 (both g/l,
25C). Stability Hydrolysed by concentrated acids; stable to light.
COMMERCIALISATION:
History Herbicide introduced by Yorkshire Tar Distillers Ltd.
APPLICATIONS:
ModeofactionSelective herbicide. Uses Used at 1.122.24 kg/ha for selective pre-em.
control of weeds in onions, potatoes and sugar beet, and at 2.24 kg/ha post-em. in brassicas
and onions when the weeds are at the seedling stage. Formulation types EC; GR .
ANALYSIS:
Product analysis is by hydrolysis with acid, distillation of the m-toluidine released which
is measured by titration. Residues may be determined by colorimetry of a derivative of
m-toluidine, which has been formed by hydrolysis.
Oral Acute oral LD50 for ratsc.2200 mg/kg. Toxicity Class WHO (a.i.) O
ENVIRONMENTAL FATE:
Soil/Environment Persists in soilc.50 d at 15C.
methocrotophos
Insecticide
IRAC1B
NOMENCLATURE:
Common name methocrotophos (BSI, E-ISO); m(tocrotophos) ((m) F-ISO)
IUPACname (E)-2-(N-methoxy-N-methylcarbamoyl)-1-methylvinyl dimethyl phosphate;
3-dimethoxyphosphinoyloxy-N-methoxy-N-methylisocrotonamide
Chemical Abstracts name (E)-3-(methoxymethylamino)-1-methyl-3-oxo-1-
propenyl dimethyl phosphate CASRN[25601847] DevelopmentcodesC 2307
SmilescodeCOCNC(=O)C=C(C)OP(=O)(OC)OC
PHYSICAL CHEMISTRY: Mol. wt. 253.2 M.f. C8H16NO6P
methocrotophos 369
COMMERCIALISATION:
History Insecticide evaluated by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
methometon
Herbicide
NOMENCLATURE:
Common name methometon (BSI, E-ISO); m(tom) ((m) F-ISO)
IUPACname 6-methoxy-N2,N4-bis(3-methoxypropyl)-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-methoxy-N,N-bis(3-methoxypropyl)-1,3,5-
triazine-2,4-diamine CASRN[1771079] DevelopmentcodesG 34 690
SmilescodeCOCCCNc1nc(NCCCOC)nc(OC)n1
COMMERCIALISATION:
methoprotryne
Herbicide
CH3S N NHCH(CH3)2
N N
NH(CH2)3OCH3
NOMENCLATURE:
Common name methoprotryn (WSSA); methoprotryne (BSI, E-ISO); m(toprotryne) ((f)
F-ISO)
IUPACname N2-isopropyl-N4-(3-methoxypropyl)-6-methylthio-1,3,5-triazine-2,4-
diamine
Chemical Abstracts name N-(3-methoxypropyl)-N-(1-methylethyl)-6-(methylthio)-
1,3,5-triazine-2,4-diamine CASRN[841065] DevelopmentcodesG 36 393
SmilescodeCOCCCNc1nc(NC(C)C)nc(SC)n1
PHYSICAL CHEMISTRY: Mol. wt. 271.4 M.f. C11H21N5OS Form Colourless powder.
M.p.6870C V.p. 0.038 mPa (20C) Henry 3.22 105 Pa m3 mol1 (calc.) S.g./density
1.186 (20C) Solubility In water 320 mg/l (20C). In acetone 450, dichloromethane 650,
hexane 5, methanol 400, octanol 150, toluene 380 (all in g/l, 20C). Stability Hydrolysed
370 methoprotryne
in aqueous alkaline and acidic media to the inactive 2-hydroxytriazine. pKa Basic, 4.0
(21C)
COMMERCIALISATION:
History Herbicide reported by A. Gast etal. (Z. Pflanzenkr. Pflanzenpathol. Pflanzenschutz,
1965, 72, 325). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents BE 584306;
GB 927348
APPLICATIONS:
site. ModeofactionSelective herbicide, absorbed by the leaves and roots. Uses Selective
post-emergence control of annual broad-leaved weeds and grasses in winter-sown cereals
at 1.52.0 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products Gesaran* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc (CIPACHandbook, 1983, 1B, 1864; 1980, 1A, 1302). Residues
determined by glc (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
Oral Acute oral LD50 for rats >5000, mice 2400 mg/kg. Skin and eye Acute percutaneous
LD50 for rats >150 mg/kg. Not a skin irritant (rats). NOEL (90 d) for rats 3750 mg a.i./kg
diet (c 250 mg a.i./kg daily); for dogs 11250 mg/kg diet (c. 375 mg/kg daily).
ECOTOXICOLOGY:
Fish LC50 (96 h) for bluegill sunfish 9.8, rainbow trout 8, and crucian carp 31 mg/l.
Bees Non-toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, the thiomethyl group is replaced by hydroxyl, presumably after oxidation
of the sulfur to sulfoxide and sulfone. Demethylation of the amino groups at C4 and C6
occurs, with cleavage of the amine moieties and their replacement by hydroxyl, presumably
followed by ring opening. Soil/Environment In soil, the thiomethyl group is replaced by
hydroxyl, presumably after oxidation of the sulfur to sulfoxide and sulfone. Demethylation
of the amino groups at C4 and C6 occurs, with cleavage of the amine moieties and their
replacement by hydroxyl, presumably followed by ring opening.
methoprotryne 371
methoquin-butyl
Insecticide
NOMENCLATURE:
Common name m(thoquine-butyl) ((m) F-ISO); methoquin-butyl (BSI, E-ISO)
IUPACname butyl 3-methylquinoline-4-carboxylate
Chemical Abstracts name butyl 3-methyl-4-quinolinecarboxylate Other names BMC
CASRN[19764433] SmilescodeCCCCOC(=O)c1c(C)cnc2ccccc12
COMMERCIALISATION:
methoxychlor
Insecticide
CH3O CH OCH3
CCl3
IRAC3B
NOMENCLATURE:
Common name methoxychlor (BSI, E-ISO, ESA, JMAF); m(thoxychlore) ((m) F-ISO)
IUPACname 1,1,1-trichloro-2,2-bis(4-methoxyphenyl)ethane
Chemical Abstracts name 1,1-(2,2,2-trichloroethylidene)bis[4-methoxybenzene]
Other names DMDT CASRN[72435] Official codes OMS 466; ENT 1716
SmilescodeCOc1ccc(cc1)C(c2ccc(OC)cc2)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade contains 88% methoxychlor and 12% related isomers.
Mol. wt. 345.7 M.f. C16H15Cl3O2 Form Colourless crystals; (tech., grey powder).
M.p.89C; (tech., 77C) V.p. Very low S.g./density 1.41 (25C) Solubility In water
0.1 mg/l (25C). Readily soluble in aromatic, chlorinated and ketonic solvents, and
vegetable oils. In chloroform and xylene 440, methanol 50 (all in g/kg, 22C).
Stability Stable to oxidising agents and to uv irradiation. Reacts with alkalis, especially in
the presence of catalytically-active metals, with loss of hydrogen chloride, but more slowly
than DDT. Colour turns to pink or tan on exposure to light.
COMMERCIALISATION:
History Insecticide reported by P. Luger etal. (Helv. Chim. Acta, 1944, 27, 892). Introduced
by J. R. Geigy AG (now Syngenta AG) and by E. I. du Pont de Nemours & Co. (neither
company now manufactures or markets it). Patents CH 226180; GB 547871 (to Ciba-
Geigy); US 2420928; US 2477655; GB 624561 (to DuPont)
372 methoxychlor
APPLICATIONS:
Biochemistry Acts on the nervous system of insects and disturbs the function of
neurons by interaction with the sodium channel. ModeofactionInsecticide with contact
and stomach action. Uses Control of a wide range of insect pests (particularly chewing
insects) in field crops, forage crops, fruit, vines, flowers, vegetables, and in forestry. Used
also for control of insect pests in animal houses, dairies, and in household and industrial
premises. Formulation types AE; DP; EC; GR; WP. Compatibility Incompatible with
highly alkaline materials.
PRODUCTS:
Discontinued products Marlate* (Kincaid); Sixanol* (Quinta).
ANALYSIS:
Product analysis by total chlorine content (H. L. Pease, J. Assoc. Off. Anal. Chem., 1976, 58, 40).
Residues determined by glc, tlc or paper chromatography (AOACMethods, 18th Ed., 970.52;
J. Solomon & W. L. Lockhart, J. Assoc. Off. Anal. Chem., 1978, 60, 690; Anal. Methods Pestic.
Plant Growth Regul., 1972, 6, 441) or colorimetrically (AOACMethods, 18th Ed., 954.09; ibid.
10th Ed., 24.14824.152). See also Pestic. Anal. Man., I, 208, 303, 304, 502; ibid., II, 180.120. In
drinking water by glc with ECD (AOACMethods, 18th Ed., 990.06).
JMPR Evaln. 29 (1977). PDS 28 (1977). ICSC.306 (1999). IARC 20 (1979).
IARC Class 3
for rabbits >2000 mg/kg. Not a skin irritant. NOEL In 1 y feeding trials, no toxic effect
observed in dogs receiving 300 mg/kg daily; in 2 y trials in rats, no effect at 200 mg/kg diet,
but some reduction in growth occurred at 1600 mg/kg diet. ADI/RfD (JMPR) 0.1 mg/kg
b.w. [1977]; (EPA) cRfD 0.005 mg/kg b.w. [1991]. Water GV 0.02 mg/l
Toxicity Class WHO (a.i.) U.
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >2000 mg/kg. Dietary LC50 (8 d) for bobwhite
quail and ring-necked pheasants >5000 mg/kg diet. Fish LC50 (24 h) for rainbow trout
0.052, bluegill sunfish 0.067 mg/l. Daphnia LC50 (48 h) 0.00078 mg/l.
ENVIRONMENTAL FATE:
Animals Degradation in animals is principally by O-dealkylation to the corresponding
phenol and diphenol, and by dehydrochlorination to 4,4-dihydroxybenzophenone (K. S.
Kapoor, J. Agric. Food Chem., 1970, 18, 11451152; J. Pestic. Sci., 1989, 14, 85; M. D. Corbett et
al., Chem. Res.Toxicol., 1990, 3, 8). Soil/Environment DT50 in waterc.46 d.
methoxychlor 373
2-methoxyethylmercury acetate
Fungicide
NOMENCLATURE:
IUPACname 2-methoxyethylmercury acetate
Chemical Abstracts name (acetato-O)(2-methoxyethyl)mercury CASRN[151382]
ECno2057902 SmilescodeCOCC[Hg]OC(=O)C
PHYSICAL CHEMISTRY: Mol. wt. 318.7 M.f. C5H10HgO3
COMMERCIALISATION:
History Fungicide introduced by Kenogard VT AB.
APPLICATIONS: Uses A fungicide used to protect seeds of cereals, cotton, flax, oilseed
rape and sugar beet from infection by Alternaria, Botrytis, Drechslera, Fusarium, Phoma,
Pythium, Rhizoctonia, Septoria and Tilletia spp. and Ustilago hordei. Formulation types LS .
PRODUCTS:
Discontinued products Panogen* (Kenogard AB).
ANALYSIS:
Product analysis by titration (AOACMethods, 18th Ed., 971.04) or gravimetrically (ibid.,
973.11).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. JMPR Evaln.
9 (1967) EU Status (1107/2009) Alkoxyalkyl mercury compounds considered to be
outside the scope of the Directive; already banned, 79/117/EEC.
IARC Class Methylmercury compounds are classified 2B
2-methoxyethylmercury silicate
Fungicide
NOMENCLATURE:
IUPACname The compound is an organomercury silicate but there is some doubt about
whether it is an orthosilicate or a metasilicate and therefore about its true molecular
structure
Chemical Abstracts name hydrogen [metasilicato(2)-O](2-methoxyethyl)
mercurate(1) CASRN[64491925]
PHYSICAL CHEMISTRY:
Form Colourless crystalline powder. V.p. 440 mPa (35C) Solubility Practically insoluble
374
2-methoxyethylmercury silicate
in water. Stability 2-Methoxyethylmercury salts are stable to alkali but are decomposed
by halogen acids (J. Chatt, Chem. Rev. 1951 48, 7).
COMMERCIALISATION:
History Fungicide introduced by I. G. Farbenindustrie AG (later Bayer AG).
APPLICATIONS: Uses In seed treatments, against various seed-borne diseases of
cereals. Formulation types DS .
PRODUCTS:
Discontinued products Ceresan Universal Dry Seed Treatment* (Bayer); Soprasan*
(Sopra).
ANALYSIS:
Product analysis by titration (CIPACHandbook, 1970, 1, 503; AOACMethods, 18th Ed., 971.04)
or gravimetry (ibid., 973.11).
JMPR Evaln. 9 (1967)
Oral Acute oral LD50 for rats 1140 mg formulated product/kg. Toxicity Class WHO (a.i.)
IIIPIC Not specifically listed in the relevant DGD, but all mercury compounds are included
in the PIC procedure.
methoxyphenone
Herbicide
NOMENCLATURE:
Common name methoxyphenone (JMAF)
IUPACname 4-methoxy-3,3-dimethylbenzophenone
Chemical Abstracts name (4-methoxy-3-methylphenyl)(3-methylphenyl)
methanone CASRN[41295287] DevelopmentcodesNK-049 (Nippon Kayaku)
SmilescodeCOc1ccc(cc1C)C(=O)c2cccc(C)c2
PHYSICAL CHEMISTRY:
Mol. wt. 240.3 M.f. C16H16O2 Form Colourless crystals. M.p.62.062.5C
Solubility In water 2 mg/l (20C). Soluble in most organic solvents. Stability Stable
under acid and alkaline conditions, but slowly decomposed by sunlight.
COMMERCIALISATION:
History Herbicide reported (Proc. Asian-Pacific Weed Sci. Soc. Conf., 4th, 1973, p. 215).
Introduced by Nippon Kayaku Co., Ltd. Patents JP 51005446; GB 1355926; US 3873304
APPLICATIONS:
Biochemistry Inhibits photosynthesis. ModeofactionSelective herbicide, inducing
chlorosis. Uses A selective pre-em. herbicide effective against annual grasses and broad-
leaved weeds in paddy rice and vegetable crops at 35 kg/ha; also used in rice pre-em. in
methoxyphenone 375
combination with bensulide, at 3050 kg granules/ha. Formulation types WP.

PRODUCTS:
Discontinued products Kayametone* (Nippon Kayaku).
ANALYSIS:
Oral Acute oral LD50 for rats and mice >4000 mg/kg. NOEL (90 d) for rats 1500 mg/kg
diet, for mice 1000 mg/kg diet. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Soil/Environment It is biodegradable, leaving no residue problems.
4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate
Chemical Abstracts name 3,5-dimethyl-4-(methyl-2-propynylamino)phenyl
methylcarbamate CASRN[23623496] DevelopmentcodesC 20 132
SmilescodeCNC(=O)Oc1cc(C)c(N(C)CC#C)c(C)c1
COMMERCIALISATION:
APPLICATIONS:
insecticide.
2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
Chemical Abstracts name 2-(methyl-2-propynylamino)phenyl methylcarbamate
CASRN[23504076] DevelopmentcodesC 17 018
SmilescodeCNC(=O)Oc1ccccc1N(C)CC#C
376
2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionContact insecticide.
5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid
Fungicide, herbicide, nematicide
NOMENCLATURE:
IUPACname 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid; tetrahydro-5-methyl-6-
thioxo-2H-1,3,5-thiadiazin-3-ylacetic acid
Chemical Abstracts name dihydro-5-methyl-6-thioxo-2H-1,3,5-thiadiazine-
3(4H)-acetic acid Other names thiadiazinthion CASRN[3655887]
SmilescodeCN1CN(CC(=O)O)CSC1=S
COMMERCIALISATION:
History Nematicide introduced by Bayer AG.
PRODUCTS:
Discontinued products Terracur* (Bayer).
methylarsenic sulfide
Fungicide
NOMENCLATURE:
IUPACname methylarsenic sulfide
Chemical Abstracts name methylthioxoarsine Other names MAS
CASRN[2533826] SmilescodeC[As]=S
PHYSICAL CHEMISTRY: Mol. wt. 122.0 M.f. CH3AsS Form Colourless flakes with
an unpleasant odour. M.p.110C Solubility Practically insoluble in water. Readily soluble
in carbon disulfide; less soluble in chlorinated hydrocarbons, DMF, diethyl ether, ethanol,
pyridine.
COMMERCIALISATION:
History Fungicidal properties of this chemical, which was reported in 1858 (von Bayer,
Ann. Chem. Pharm., 1858, 107, 279), described in 1931. Introduced by Bayer AG (1958).
Patents DE 1079886
APPLICATIONS: Uses Used as a seed or soil treatment to control Rhizoctonia solani
and other soil fungi.
methylarsenic sulfide 377

PRODUCTS:
Discontinued products Rhizoctol* (Bayer); Urbasulf* (Bayer);
Discontinuedmixtures Rhizoctol combi* (+benquinox) (Bayer); Rhizoctol slurry*
(+benquinox) (Bayer).
ANALYSIS:
Product analysis is by conversion to arsine which was measured by titration with bromine.
Residues may be determined by a colorimetric method after conversion to arsenate (H.
Frehse & H.Tietz, J. Agric. Food Chem., 1959, 7, 553).
rabbits 1400 mg/kg. Skin irritation occurred to 6 persons after a 4-h exposure of a
moistened formulation (equivalent to 48 g arsenic/kg). ECClassification Not specified,
but arsenic compounds in general (with exceptions) are assigned T; R23/25| N; R50, R53|
concn. dep.
methyldymron
Herbicide
CH3
C NHCON
CH3 CH3
HRACZ
NOMENCLATURE:
Common name methyldymron (JMAF)
IUPACname 1-methyl-3-(1-methyl-1-phenylethyl)-1-phenylurea; 3-(,-dimethylbenzyl)-
1-methyl-1-phenylurea
Chemical Abstracts name N-methyl-N-(1-methyl-1-phenylethyl)-N-phenylurea
CASRN[42609734] DevelopmentcodesK-1441; SK-41 (SDS Biotech KK)
SmilescodeCN(C(=O)NC(C)(C)c1ccccc1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 268.4 M.f. C17H20N2O Form Colourless, odourless
crystals. M.p.72C Kow logP = 3.01 S.g./density 1.11.2 Solubility In water 120 mg/l
(20C). In acetone 913, hexane 8.2, methanol 637 (all in g/l, 20C).
Stability Stable to heat and uv light.
COMMERCIALISATION:
History Herbicide reported by T. Takematsu etal. (Proc. 5th Asian-Pacific Weed Sci. Soc.
Conf., 1975, 121). Introduced in Japan (1978) by Showa Denko (agrochemical interests
later SDS Biotech K.K.). Patents JP 7242493
378 methyldymron
APPLICATIONS:
Biochemistry Cell division inhibitor. ModeofactionSelective herbicide, absorbed
principally by the roots, with translocation to the meristem. Uses Pre- and early post-
emergence control of cyperaceous and some annual grass weeds in turf, at 210 kg/ha.
PRODUCTS:
Discontinued products Stacker* (SDS Biotech K.K.).
ANALYSIS:
Product and residue analysis by glc and hplc; details available from SDS Biotech.
Oral Acute oral LD50 for male mice 5000, female mice 5269, male rats 5852, female rats
3948 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg.
Inhalation LC50 (14 d) for rats >4.85 mg/l. NOEL (90 d) for male rats 26.4, female rats
25.6 mg/kg diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 14 mg/l. Daphnia LC50 (3 h) for D. pulex >40 ppm.
ENVIRONMENTAL FATE:
Plants Rapidly metabolised in plants.
methyl isothiocyanate
Fungicide, herbicide, insecticide, nematicide
CH3NCS
NOMENCLATURE:
Common name isothiocyanate de m(thyle) (F-ISO, accepted in lieu of a common
name); methyl isothiocyanate (BSI, E-ISO, JMAF, accepted in lieu of a common name)
IUPACname methyl isothiocyanate
Chemical Abstracts name isothiocyanatomethane Other names MIT; MITC
CASRN[556616] ECno2091325 SmilescodeCN=C=S
PHYSICAL CHEMISTRY:
Composition Tech. is 94.5% pure. Mol. wt. 73.1 M.f. C2H3NS Form Colourless
crystals, with a horseradish-like odour. M.p.3536C; (tech., 25.327.6C)
B.p. 118119C V.p. 2.13 kPa (25C) Kow logP = 1.37 (calc.) S.g./density 1.069 (37C);
(tech., 1.0537 (40C)) Solubility In water 8.2 g/l (20C). Readily soluble in common
organic solvents, such as ethanol, methanol, acetone, cyclohexanone, dichloromethane,
chloroform, carbon tetrachloride, benzene, xylene, petroleum ether and mineral oils.
Stability Unstable and reactive. Rapidly hydrolysed by alkalis, more slowly in acidic and
neutral solutions, DT50 85 h (pH 5), 490 h (pH 7), 110 h (pH 9) (25C). Sensitive to oxygen
and to light. Stable up to 200C. pKa 12.3 F.p. 26.9C
methyl isothiocyanate 379

COMMERCIALISATION:
History Nematicidal activity reported by E. A. Pieroh etal. (Anz. Schdlingsskd., 1959, 32,
183). Introduced by Schering AG (now Bayer AG). Patents US 3113908
Manufacturers Bayer CropScience
APPLICATIONS: Uses Multi-purpose soil fumigant for control of nematodes, soil fungi,
soil insects, and weed seeds. Phytotoxicity Phytotoxic to all green plants.
PRODUCTS:
Discontinued products Trapex* (Aventis); Trapexide* (Aventis).
ANALYSIS:
Product analysis by glc or by hplc. Residues determined by glc with FPD (M. Ottnad et
al., Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 563). Details available from Bayer
CropScience.
percutaneous LD50 for rats 2780, male mice 1870, rabbits 263 mg/kg. Strongly irritating to
eyes and skin (rabbits). Inhalation LC50 (1 h) for rats 1.9 mg/l air. NOEL (2 y) for rats
10 mg/l drinking water (0.370.56 mg/kg b.w. daily); (2 y) for mice 20 mg/l drinking water
(3.48 mg/kg b.w. daily); (1 y) for dogs 0.4 mg/kg b.w.. daily (by gavage). ADI/RfD (BfR)
0.004 mg/kg b.w. [2005]. Other Not carcinogenic. Toxicity Class WHO (a.i.) II.
ECClassification T; R23/25| C; R34| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 136 mg/kg. Dietary LC50 (5 d) for mallard ducks
10936, pheasants >5000 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.14, rainbow
trout 0.09, mirror carp 0.370.57 mg/l. Daphnia LC50 (48 h) 0.055mg/l. Algae EC50 (96 h)
0.248 mg/l; NOEC (96 h) 0.125 mg/l. Bees Not hazardous to bees when used as directed.
ENVIRONMENTAL FATE:
Soil/Environment In damp soil, degradation and evaporation of the bulk of the substance
occurs within 3 weeks at 1820C soil temperature, 4 weeks at 612C, and 8 weeks at
06C. At the lower temperatures, leaching is more significant and is dependent on soil
moisture. The potential for groundwater contamination is small, due to low leaching and
fast degradation.
380 methyl isothiocyanate

methylmercury dicyandiamide
Fungicide
NOMENCLATURE:
Common name methylmercury dicyandiamide (BSI, accepted in lieu of a common
name.)
IUPACname 1-cyano-3-(methylmercurio)guanidine; (methylmercurio)
guanidinocarbonitrile
Chemical Abstracts name (cyanoguanidinato-N)methylmercury CASRN[502396]
SmilescodeC[Hg]NC(=N)NC#N
PHYSICAL CHEMISTRY: Mol. wt. 298.7 M.f. C3H6HgN4
COMMERCIALISATION:
History Fungicide introduced in Sweden in 1938, and in USA by Panogen Inc.
PRODUCTS:
Discontinued products Panogen* (Panogen).
IARC Class methylmercury compounds are classified 2B.
Toxicity Class WHO (a.i.) O ECClassification Not specified, but organic mercury
generally is assigned T+; R26/27/28| R33| N; R50, R53 (concentration-dependent). PIC Yes.
3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPACname 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate
Chemical Abstracts name 3-methyl-1-phenyl-1H-pyrazol-5-yl dimethylcarbamate
SmilescodeCN(C)C(=O)Oc1cc(C)nn1c2ccccc2
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrolan* (Ciba-Geigy).
3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate 381

metobenzuron
Herbicide
CH3 CH3
CH3 CH3
O O NHCON
CH3O OCH3
NOMENCLATURE:
Common name m(tobenzuron) ((m) F-ISO); metobenzuron (BSI, E-ISO)
IUPACname ()-1-methoxy-3-[4-(2-methoxy-2,4,4-trimethylchroman-7-yloxy)phenyl]-1-
methylurea
Chemical Abstracts name ()-N-[4-[(3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-
1-benzopyran-7-yl)oxy]phenyl]-N-methoxy-N-methylurea CASRN[111578326]
DevelopmentcodesUMP-488 (Mitsui Petrochemical)
SmilescodeCON(C)C(=O)Nc1ccc(Oc2ccc3c(OC(C)(CC3(C)C)OC)c2)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 400.5 M.f. C22H28N2O5 Form White powder. M.p.101.0102.5C
Solubility In water 0.4 mg/l (25C).
COMMERCIALISATION:
History Reported by T. Morimoto etal. (Proc. Br. Crop Prot. Conf. Weeds, 1993, 1, 67).
Introduced by Mitsui Petrochemical Industries Ltd (became Mitsui Chemicals Inc.).
APPLICATIONS:
Biochemistry Inhibitor of photosynthesis. Uses Selective post-emergence herbicide for
control of a wide range of broad-leaved weeds, including triazine-resistant weeds, in maize.
Application rates 125250 g/ha.
Compatibility Combination with 2,4-D increases efficacy and widens the weed spectrum.
LD50 for rabbits >2000 mg/kg. Non-irritating to skin and slightly irritating to eyes (rabbits).
NOEL (2 y) for rats 75 ppm (4.4 mg/kg b.w.) (EPA Tracking). ADI/RfD (EPA) 0.04 mg/kg
b.w. [1993]. Other Non-mutagenic in the Ames Test.
ENVIRONMENTAL FATE:
Soil/Environment DT50 in soil 4 h (under irradiation), 8 h (in the dark). Low mobility in
sandy loam soil.
382 metobenzuron
metolcarb
Insecticide
O
C
O NHCH3
CH3
IRAC1A; carbamate
NOMENCLATURE:
Common name metolcarb (BSI, E-ISO); m(tolcarb) ((m) F-ISO); MTMC (JMAF)
IUPACname m-tolyl methylcarbamate
Chemical Abstracts name 3-methylphenyl methylcarbamate CASRN[1129415]
ECno2144460 DevelopmentcodesC-3 (Nihon Nohyaku)
SmilescodeCNC(=O)Oc1cccc(C)c1
PHYSICAL CHEMISTRY: Mol. wt. 165.2 M.f. C9H11NO2 Form Tech. is a colourless
solid. M.p.7677C; 7475C (tech.) V.p. 145 mPa (20C) Solubility In water 2.6 g/l
(30C). Soluble in polar organic solvents e.g. in cyclohexanone 790, xylene 100 (both in g/
kg, 30C), methanol 880 g/kg (room temperature). Sparingly soluble in non-polar solvents.
COMMERCIALISATION:
History Insecticide introduced by Nihon Nohyaku Co., Ltd and by Sumitomo Chemical
Co., Ltd.
Manufacturers Hunan Haili; Saeryung
APPLICATIONS:
contact and respiratory action. Uses Control of planthoppers, leafhoppers, and
other sucking insects on rice. Also used for control of citrus mealybugs, onion thrips,
Mediterranean fruit flies, pink bollWorms and cotton aphids. Formulation types DP; EC;
MG; WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Metacrate* (Sumitomo Chemical); Tsumacide* (Nihon
Nohyaku); Discontinuedmixtures Ofunack M* (+pyridaphenthion) (Mitsui Chemicals
Agro).
ANALYSIS:
Product analysis by glc or by hplc (S. Sakaue et al., Nippon Nogei Kagaku Kaishi, 1981, 55,
1237). Residues determined by glc of a derivative with ECD (J. Miyamoto et al., Nihon
Noyaku Gakkaishi, 1978, 3, 119).
metolcarb 383
Oral Acute oral LD50 for male rats 580, female rats 498, mice 109 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Inhalation LC50 for rats
0.475 mg/l air. Toxicity Class WHO (a.i.) II ECClassification Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Fish Low toxicity to fish.
ENVIRONMENTAL FATE:
Animals Metabolism of carbamate insecticides is reviewed (M. Cool & C. K. Jankowski in
Insecticides).
metsulfovax
Fungicide
NOMENCLATURE:
Common name metsulfovax (BSI, ANSI, E-ISO, (m) F-ISO)
IUPACname 2,4-dimethyl-1,3-thiazole-5-carboxanilide; 2,4-dimethylthiazole-5-
carboxanilide
Chemical Abstracts name 2,4-dimethyl-N-phenyl-5-thiazolecarboxamide
CASRN[21452186] DevelopmentcodesG696
SmilescodeCc1nc(C)c(s1)C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 232.3 M.f. C12H12N2OS Form Crystals.
M.p.140142C V.p. 0.0017 mPa (25C) S.g./density 1.27 Solubility In water
342 mg/l. In hexane 0.32, methanol 171, toluene 12.9 (all in g/l). pKa 2.05
COMMERCIALISATION:
History Fungicide evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Biochemistry Inhibitor of succinate dehydrogenase complex, in the respiratory electron
transport chain. ModeofactionSystemic fungicide. Uses Control of Puccinia, Ustilago,
Rhizoctonia solani, Tilletia spp., and other Basidiomycetes in cereals, cotton, potatoes, and
ornamentals. Applied to foliage or as a seed treatment at 2080 g/100 kg seed or up to
1 kg/ha foliar application. Formulation types FS; SC. WS .
PRODUCTS:
Discontinued products Provax* (Uniroyal).
rabbits >2000 mg/kg. Inhalation LC50 (4 h) for rats >5.7 mg/l air. NOEL (2 y) for female
rats 50 mg/kg diet, for male rats 400 mg/kg diet. ADI/RfD (BfR) 0.025 mg/kg b.w. [1991].
384 metsulfovax

ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks >5620 mg/kg diet. Fish LC50 (96 h) for bluegill
sunfish 34 mg/l. Daphnia LC50 (48 h) >97 mg/l.
ENVIRONMENTAL FATE:
mexacarbate
NOMENCLATURE:
Common name mexacarbate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname 4-dimethylamino-3,5-xylyl methylcarbamate
Chemical Abstracts name 4-(dimethylamino)-3,5-dimethylphenyl methylcarbamate
CASRN[315184] ECno2062493 DevelopmentcodesDowco 139
SmilescodeCNC(=O)Oc1cc(C)c(N(C)C)c(C)c1
PHYSICAL CHEMISTRY: Mol. wt. 222.3 M.f. C12H18N2O2 M.p.85C V.p. 1.33
104 mPa Solubility In water 1000 ppm (25C). In xylene 5.1 104, benzene 1.02 105,
ethanol 1.16 105, acetone 1.16 105 (all in ppm, 25C).
COMMERCIALISATION:
History Insecticide introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
PRODUCTS:
Discontinued products Zectran* (DowElanco).
EHC 64 (1986; a review of carbamate pesticides in general). IARC 12 (1976).
IARC Class 3
Toxicity Class WHO (a.i.) O ECClassification T+; R28| Xn; R21| N; R50, R53
mexacarbate 385
MG 191
Herbicide safener
CH3 CHCl2
O O
NOMENCLATURE:
IUPACname 2-dichloromethyl-2-methyl-1,3-dioxolane
CASRN[22052637] DevelopmentcodesMG 191 SmilescodeCC1(OCCO1)
C(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 171.0 M.f. C5H8Cl2O2 B.p. 9192C /4 kPa
Kow logP = 1.24 Solubility In water 9.75 g/l. Soluble in protic and aprotic organic solvents.
Stability Stable 24 w at 54C; stable 40 w at 10 klux (25C). Stable to hydrolysis at pH 4,
6 and 8.
COMMERCIALISATION:
History Reported by F. Dutka etal. (Proc. Br. Crop Prot. Conf. Weeds, 1987, 1, 7784).
Herbicide safener developed by Nitrokmia Ipartelepek.
APPLICATIONS:
Biochemistry Increases glutathione synthesis and glutathione-related enzyme activity
in protected plants. ModeofactionReadily absorbed by maize roots and translocated.
Uses A safener for thiocarbamate herbicides.
Oral Acute oral LD50 for male rats 465, female rats 492, male and female mice 653 mg/kg.
milneb
Fungicide
NOMENCLATURE:
Common name milneb (BSI, ANSI); thiadiazine (JMAF)
IUPACname 4,4,6,6-tetramethyl-3,3-ethylenedi-1,3,5-thiadiazinane-2-thione
Chemical Abstracts name 3,3-(1,2-ethanediyl)bis[tetrahydro-4,6-dimethyl-2H-
1,3,5-thiadiazine-2-thione] CASRN[3773497] DevelopmentcodesExperimental
Fungicide 328 SmilescodeCC1NC(C)N(CCN2C(C)NC(C)SC2=S)C(=S)S1
PHYSICAL CHEMISTRY: Mol. wt. 350.6 M.f. C12H22N4S4
COMMERCIALISATION:
History Fungicide evaluated by E. I. du Pont de Nemours & Co.
PRODUCTS:
Discontinued products Banlate* (DuPont).
386 milneb
mipafox
NOMENCLATURE:
Common name mipafox (BSI, E-ISO, (m) F-ISO)
IUPACname N,N-diisopropylphosphorodiamidic fluoride
Chemical Abstracts name N,N-bis(1-methylethyl)phosphorodiamidic fluoride
CASRN[371868] ECno2067423 DevelopmentcodesPestox 15
SmilescodeCC(C)NP(=O)(F)NC(C)C
PHYSICAL CHEMISTRY: Mol. wt. 182.2 M.f. C6H16FN2OP
COMMERCIALISATION:
History Insecticide and acaricide introduced by Pest Control Ltd (later Schering
Agrochemicals).
PRODUCTS:
Discontinued products Isopestox* (Schering).
Toxicity Class WHO (a.i.) O ECClassification T+; R39/26/27/28
mirex
Insecticide
NOMENCLATURE:
Common name mirex (ESA)
IUPACname dodecachloropentacyclo[5.3.0.02,6.03,9.04,8]
decane; perchloropentacyclo[5.3.0.02,6.03,9.04,8]decane;
dodecachloropentacyclo[5.2.1.02,6.03,9.05,8]decane
Chemical Abstracts name 1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1,3,4-
metheno-1H-cyclobuta[cd]pentalene Other names perchlordcone
CASRN[2385855] ECno2191966 DevelopmentcodesGC 1283 (Allied)
SmilescodeClC1(C2(Cl)C3(Cl)C4(Cl)C5(Cl)C1(Cl)C3(Cl)Cl)C5(Cl)C(Cl)(Cl)C24Cl
PHYSICAL CHEMISTRY: Mol. wt. 545.5 M.f. C10Cl12 V.p. 0.1 mPa (Residue Reviews,
103, 1 (1988)) Solubility In water 7 105 ppm (22C) (Residue Reviews, 103, 1 (1988)).
In dioxane 1.53 105, benzene 1.22 105, carbon tetrachloride 7.2 104, methyl ethyl
ketone 5.6 104 (all in ppm, room temperature).
COMMERCIALISATION:
History Insecticide introduced by Allied Chemical Corp., Agricultural Div. (later Hopkins
Ltd).
APPLICATIONS:
ModeofactionIngested insecticide.
mirex 387
PRODUCTS:
Discontinued products Dechlorane* (Allied); Mirex* (Seppic).
ANALYSIS:
Residues determined by glc with ECD, tlc or paper chromatography (AOACMethods, 18th
Ed., 977.19, 980.22, 970.52). See also Pestic. Anal. Man., I, 303.
EHC 44 (1984). HSG 39 (1990). IARC 20 (1979). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EEEC, as amended by
IARC Class 2B
NOEL NOAEL for rats 1 ppm (0.07 mg/kg b.w.) (EPA IRIS). ADI/RfD (EPA) cRfD 0.0002
mg/kg b.w. [1992]. Water GV Excluded from GV derivation (U). Toxicity Class WHO
(a.i.) O ECClassification R40| R62, R63| R64| Xn; R21/22| N; R50, R53
MNFA
Acaricide
NOMENCLATURE:
Common name MNFA (JMAF)
IUPACname 2-fluoro-N-methyl-N-1-naphthylacetamide
Chemical Abstracts name 2-fluoro-N-methyl-N-(1-naphthalenyl)acetamide
CASRN[5903139] DevelopmentcodesNA-26
SmilescodeCN(C(=O)CF)c1cccc2ccccc12
PHYSICAL CHEMISTRY: Mol. wt. 217.2 M.f. C13H12FNO
COMMERCIALISATION:
History Acaricide introduced by Nippon Soda Co., Ltd.
PRODUCTS:
Discontinued products Nissol* (Nippon Soda).
monalide
Herbicide
NOMENCLATURE:
Common name monalide (BSI, E-ISO, (f) F-ISO)
IUPACname 4-chloro-2,2-dimethylvaleranilide; 4-chloro-,-dimethylvaleranilide
Chemical Abstracts name N-(4-chlorophenyl)-2,2-dimethylpentanamide
CASRN[7287367] DevelopmentcodesSchering 35 830 (AgrEvo)
388 monalide
SmilescodeCCCC(C)(C)C(=O)Nc1ccc(Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 239.7 M.f. C13H18ClNO Form Colourless crystals.
M.p.8788C V.p. 0.24 mPa (25C) Henryc.2.52 103 Pa m3 mol1 (calc.)
Solubility In water 22.8 mg/l (23C). In cyclohexanonec.500, xylene 100, petroleum
ether <10 (all in g/l, 23C). Stability Stable to at least 50C and to hydrolysis (room
temperature) at pH 7; DT50 154 d (pH 5), 116 d (pH 8.95).
COMMERCIALISATION:
History Herbicide reported by F. Arndt (Z. Pflanzenkr. Pflanzenpathol. Pflanzenschutz, 1965,
Sonderheft III, p. 277). Introduced by Schering AG (later AgrEvo GmbH).
Patents GB 971819
APPLICATIONS:
ModeofactionSelective, systemic herbicide, absorbed by the leaves and roots.
Uses Post-emergence control of broad-leaved weeds in umbelliferous crops, such as
carrots, parsley, celery, and dill at 4 kg /ha . Formulation types EC.
PRODUCTS:
Discontinued products Potablan* (AgrEvo).
ANALYSIS:
Product analysis by hplc. Residues determined by glc after hydrolysis to 4-chloroaniline and
bromination.
LD50 for rats and rabbits >800 mg a.i. (as EC)/kg. NOEL (28 d) for rats 150 mg/kg daily.
ECOTOXICOLOGY:
Fish LC50 for guppies >100 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In soil (laboratory conditions) DT50 30 d (pH 4.85), 48 d (pH 5.2), 59
d (pH 10.8). Degradation is presumably by ring hydroxylation, degradation to the aniline
derivative, and ring opening. Duration of residual activity in soil isc.68 weeks.
monisouron
Herbicide
NOMENCLATURE:
Common name monisouron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-methylurea; 1-(5-tert-butylisoxazol-3-yl)-
3-methylurea
monisouron 389
Chemical Abstracts name N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-N-methylurea

CASRN[55807460] DevelopmentcodesSSH-41
SmilescodeCNC(=O)Nc1cc(on1)C(C)(C)C
COMMERCIALISATION:
History Herbicide introduced by Shionogi & Co., Ltd.
monuron; monuron-TCA
Herbicide
NOMENCLATURE:
Common name monuron (BSI, E-ISO, F-ISO, ANSI, WSSA); monuron-TCA (WSSA for
the trichloroacetate salt (ii)); chlorfenidim* (former exception, USSR); CMU (JMAF)
IUPACname 3-(4-chlorophenyl)-1,1-dimethylurea (i); 3-(4-chlorophenyl)-1,1-
dimethyluronium trichloroacetate (ii)
Chemical Abstracts name N-(4-chlorophenyl)-N,N-dimethylurea (i); trichloroacetic
acid compound with N-(4-chlorophenyl)-N,N-dimethylurea (1:1) (ii); 3-(p-chlorophenyl)-
1,1-dimethylurea (i) CASRN[150685] monuron (i); [140410] monuron-
TCA (ii) ECno2057661 (i) DevelopmentcodesGC-2996 (Allied) (for (ii))
Smilescodemonuron:CN(C)C(=O)Nc1ccc(Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 198.7; (monuron-TCA 362.0) M.f. C9H11ClN2O
(monuron); C11H12Cl4N2O3 (monuron-TCA) Form Monuron and monuron-TCA are
crystalline solids. M.p.174175C; (monuron-TCA 7881C) V.p. 0.067 mPa (25C)
(monuron) Kow logP = 1.46, 2.12 (Agchem. Desk Ref.) Henry 5.79 105 Pa m3 mol1
(25C, calc.) S.g./density 1.27 (20C) Solubility Monuron: In water 230 mg/l (25C).
In acetone 52 g/kg (27C); sparingly soluble in petroleum oils and in polar organic
solvents. Monuron-TCA: In water 918 mg/l (room temperature). In 1,2-dichloroethane
400, methanol 177, xylene 91 (all in g/kg, room temperature). Stability Decomposes at
185200C; rate of hydrolysis at room temperature and pH 7 negligible, but increases at
elevated temperatures and under acidic or alkaline conditions.
COMMERCIALISATION:
History Herbicidal activity of monuron reported by H. C. Bucha & C. W. Todd (Science,
1951, 114, 493). Introduced by E. I. du Pont de Nemours & Co. and, as the trichloroacetate,
by Allied Chemical Corp., Agricultural Division (later Hopkins Agricultural Chemical Co.).
Patents US 2655445; GB 691403; GB 692589; US 2782112; US 2801911
Manufacturers Hermania
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. ModeofactionTotal herbicide, absorbed via
the roots. Uses It was recommended at 1030 kg/ha for total weed control in non-crop
areas; 510 kg/ha for annual maintenance. Monuron-TCA was used at 1015 kg/ha for total
390 monuron; monuron-TCA

weed control of uncropped areas. Formulation types WP (monuron).

Compatibility Acidic in reaction and incompatible with alkaline materials.
PRODUCTS:
Discontinued products Telvar* ((i)) (DuPont); Urox* ((ii)) (Allied).
ANALYSIS:
Product analysis of monuron by hydrolysis and titration of the liberated amine
(CIPACHandbook, 1980, 1A, 1310) and of monuron-TCA by i.r. spectrometry. Impurities
determined by tlc (ibid., 1994, F, 336). Residues of monuron determined by glc (Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 664) or by hplc.
IARC 53 (1991). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
IARC Class 3
Oral Monuron: Acute oral LD50 for rats 3600 mg/kg. Monuron-TCA: Acute oral LD50
for rats 23003700 mg (in corn oil)/kg. Skin and eye Application of monuron to intact
or abraded skin of guinea-pigs produced no irritation or sensitisation. Monuron-TCA is
irritating to skin and mucous membranes. NOEL for rats and dogs 250500 mg/kg diet
(M C. Hodge et al., AMA Arch. Ind. Health, 1958, 17, 45). Toxicity Class WHO (a.i.) U (also
for monuron-TCA) ECClassification R40| Xn; R22| N; R50, R53 (i): R40| Xi; R36/38| N;
R50, R53 (ii)
ENVIRONMENTAL FATE:
Soil/Environment Slowly decomposed in moist soils.
morfamquat dichloride; morfamquat

Herbicide
NOMENCLATURE:
Common name morfamquat (BSI, E-ISO, (m) F-ISO)
IUPACname 1,1-bis(3,5-dimethylmorpholinocarbonylmethyl)-4,4-bipyridinium
Chemical Abstracts name 1,1-bis[2-(3,5-dimethyl-4-morpholinyl)-2-oxoethyl]-
4,4-bipyridinium CASRN[4636833] morfamquat dichloride ECno2250628
morfamquat dichloride DevelopmentcodesPP745
PHYSICAL CHEMISTRY:
Mol. wt. 468.6; (morfamquat dichloride 539.5) M.f. C26H36N4O4; (morfamquat dichloride
C26H36Cl2N4O4)
COMMERCIALISATION:
History Dichloride introduced as herbicide (H. M. Fox, Proc. Br.Weed Control Conf., 7th,
1964, 29; H. M. Fox & C. R. Beech, ibid., p. 108) by ICI Plant Protection Div. (later ICI
Agrochemicals).
morfamquat dichloride; morfamquat 391

APPLICATIONS:
ModeofactionSystemic herbicide.
PRODUCTS:
Discontinued products Morfoxone* (ICI).
Toxicity Class WHO (a.i.) O ECClassification Xn; R22| Xi; R36/37/38| R52, R53
(assigned to morfamquat and to its dichloride)
morphothion
IRAC1B
NOMENCLATURE:
Common name morphothion (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname O,O-dimethyl S-morpholinocarbonylmethyl phosphorodithioate
Chemical Abstracts name O,O-dimethyl S-[2-(4-morpholinyl)-2-oxoethyl]
phosphorodithioate CASRN[144412] ECno2056280
SmilescodeCOP(=S)(OC)SCC(=O)N1CCOCC1
PHYSICAL CHEMISTRY:
Mol. wt. 285.3 M.f. C8H16NO4PS2
COMMERCIALISATION:
History Systemic insecticide introduced by Sandoz AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide.
PRODUCTS:
Discontinued products Ekatin M* (Sandoz).
ECClassification T; R23/24/25| N; R50, R53
mucochloric anhydride
Fungicide
NOMENCLATURE:
IUPACname 2,2,3,3-tetrachloro-4,4-oxydibut-2-en-4-olide; 5,5-oxybis(3,4-dichloro-
5H-furan-2-one) Chemical Abstracts name 5,5-oxybis[3,4-dichloro-2(5H)-furanone]
392 mucochloric anhydride

Other names mucochloric anhydride CASRN[4412093]

DevelopmentcodesGC 2466
SmilescodeClC1=C(Cl)C(=O)OC1OC2OC(=O)C(=C2Cl)Cl
COMMERCIALISATION:
History Fungicide reported by A. E. Rich (Plant Dis. Rep., 1960, 44, 306). Evaluated by Allied
Chemical Corp., Agrochemical Div. (later Hopkins Ltd).
myclozolin
Fungicide
NOMENCLATURE:
Common name myclozoline ((f) F-ISO); myclozolin (BSI, E-ISO)
IUPACname (RS)-3-(3,5-dichlorophenyl)-5-methoxymethyl-5-methyl-1,3-oxazolidine-
2,4-dione
Chemical Abstracts name 3-(3,5-dichlorophenyl)-5-(methoxymethyl)-5-methyl-2,4-
oxazolidinedione CASRN[54864618] DevelopmentcodesBAS 436F (BASF)
SmilescodeCOCC1(C)OC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
PHYSICAL CHEMISTRY: Mol. wt. 304.1 M.f. C12H11Cl2NO4 Form Colourless
crystalline solid. M.p.111C V.p. 0.059 mPa (20C) Henry 2.68 103 Pa m3 mol1 (calc.)
Solubility In water 6.7 mg/kg (20C). In chloroform 400, ethanol 20 (both g/kg, 20C).
Stability Hydrolysed under alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer & B. Zeeh (Meded. Fac. Landbouwwet. Rijksuniv.
Gent, 1982, 47, 935). Introduced by BASF AG. Patents DE 2324591
APPLICATIONS:
ModeofactionContact fungicide. Uses Diseases caused by Botrytis, monilia, sclerotinia
spp. are controlled on beans, cucumbers, grapes, groundnuts, lettuce, oilseed rape,
ornamentals, stone fruit, strawberries, sunflowers, tomatoes. Formulation types SC. WP.
ANALYSIS:
Product analysis is by glc with FID. Residues may be determined by glc with ECD.
rats >2000 mg/kg. Toxicity Class WHO (a.i.) U
myclozolin 393
naphthalene
NOMENCLATURE:
Common name naphtal(ne) (F-ISO); naphthalene (BSI, E-ISO, accepted in lieu of a
common name)
IUPACname naphthalene (I)
Chemical Abstracts name (I) CASRN[91203] Smilescodec1ccc2ccccc2c1
PHYSICAL CHEMISTRY: Mol. wt. 128.2 M.f. C10H8 Form Colourless flaky crystals.
M.p.80C B.p. 218C V.p. 6500 mPa (20C) Henry 2.78 101 Pa m3 mol1 (calc.)
S.g./density 1.517 (15C) Solubility In water 30 mg/l (room temperature). In benzene,
toluene 285, carbon tetrachloride, chloroform 500, ethanol, methanol 77 (all in g/l).Very
soluble in 1,2-dichloroethane, diethyl ether. F.p. 79C (open cup), 88C (closed cup)
COMMERCIALISATION:
History Has long been used as a household fumigant against clothes moths.
APPLICATIONS:
ModeofactionFumigant insecticide. Uses Its effectiveness as a household fumigant
against clothes moths has been questioned (W. S. Abbott & S. C. Billings, J. Econ. Entomol.,
1935, 28, 493). Has been used as a fumigant against soil fungi, but is rapidly decomposed by
soil micro-organisms.
ANALYSIS:
Product analysis by distillation from mixtures in the presence of ethanol and precipitation
as the picrate (D. S. Binnington & W. F. Giddes, Ind. Eng. Chem. Anal. Ed., 1934, 6, 461; W. L.
Millar, J. Assoc. Off. Agric. Chem., 1934, 17, 308).
ICSC.667 (2005). IARC 82 (2002). EU Status (1107/2009) Not approved, 2004/129/EC.
IARC Class 2B
Oral Acute oral LD50 for rats 2200 mg/kg. NOEL NOAEL for rats 71 mg/kg daily (EPA
IRIS). ADI/RfD (EPA) aRfD 0.4 mg/kg b.w., cRfD 0.1 mg/kg b.w. [2008].
Toxicity Class WHO (a.i.) U; (WHO Recommended Classification gives O)
ECClassification R40| Xn; R22| N; R50, R53
naphthalic anhydride
Herbicide safener
NOMENCLATURE:
Common name naphthalic anhydride (draft E-ISO, is used in lieu of common name)
IUPACname naphthalene-1,8-dicarboxylic anhydride
Chemical Abstracts name 1H,3H-naphtho[1,8-cd]pyran-1,3-dione CASRN[81845]
394 naphthalic anhydride

SmilescodeO=C1OC(=O)c2cccc3cccc1c23
PHYSICAL CHEMISTRY:
Composition Tech. is 98%. Mol. wt. 198.2 M.f. C12H6O3 Form Light tan crystalline
solid. M.p.270274C Solubility Relatively insoluble in water and most non-polar
solvents; in DMF 13.9 g/l. Stability Stable under normal storage conditions; non-
hygroscopic.
COMMERCIALISATION:
History Enhancement of the selectivity of thiocarbamate herbicides to maize reported by
O. L. Hoffman (Weed Sci. Soc. Am., Abstr., 1969, No. 12) and reviewed by G. R. Stephenson
& F.Y. Chang (in Chem. Action Herbic. Antid., p. 35). Introduced by Gulf Oil Corp.
Patents US 3131509; US 3564768
APPLICATIONS:
55(11) 10431058). Uses Used as a seed coating, at 5 g/kg seed, prior to planting and
protects maize from damage by EPTC, vernolate and related thiocarbamate herbicides.
Germination of maize seed planted 2 y after treatment was not affected.
Formulation types TC.
PRODUCTS:
Discontinued products Protect* (Gulf).
ANALYSIS:
Residues in crops determined by glc with ECD (J. R. Riden, Anal. Methods Pestic. Plant Growth
Regul., 1976, 8, 483).
rabbits >2025 mg/kg. Moderate irritant to eyes of albino rabbits. Inhalation Inhalation
of the dust by rats for 4 h at 820 mg/m3 air revealed no toxic symptom. NOEL In 90 d
feeding trials, no ill-effect noted for rats and dogs receiving 500 mg/kg diet.
naphthalic anhydride 395

naproanilide
Herbicide
CH3 O
CH C
O NH
HRACK3 WSSA 15; alkanamide (acetamide)

NOMENCLATURE:
Common name naproanilide (JMAF)
IUPACname 2-(2-naphthyloxy)-N-phenylpropionamide
Chemical Abstracts name 2-(2-naphthalenyloxy)-N-phenylpropanamide
CASRN[52570168] unstated stereochemistry DevelopmentcodesMT-101 (Mitsui
Toatsu) SmilescodeCC(Oc1ccc2ccccc2c1)C(=O)Nc3ccccc3
PHYSICAL CHEMISTRY: Mol. wt. 291.3 M.f. C19H17NO2 Form Whitish crystals.
M.p.128C V.p. 2.8 106 mPa (20C) S.g./density 1.256 (25C) Solubility In water
0.75 mg/l (27C). In acetone 171, toluene 42, ethanol 17, benzene 46 (all in g/l, 27C).
Stability Dilute aqueous solutions slowly degraded by uv light; solid stable to light.
F.p. 110C
COMMERCIALISATION:
History Herbicide reported by S. Fujisawa (Jpn. Pestic. Inf., 1981, No. 39, p. 19). Introduced
by Mitsui Toatsu Chemicals, Inc. (later Mitsui Chemicals, Inc.).
APPLICATIONS:
Biochemistry The active principle is thought to be the corresponding carboxylic acid.
ModeofactionSelective herbicide, absorbed through stems and roots. Uses Controls
annual and some perennial weeds, but not Echinochloa crus-galli, in paddy rice, at
23 kg/ha. Gives good control of young Sagittaria pygmaea. Phytotoxicity Phytotoxic to
direct seeding rice at high dosages. Formulation types GR .
PRODUCTS:
Discontinued products Uribest* (Mitsui Chemicals Agro).
ANALYSIS:
Product and residue analysis by hplc (Gotoh, J. Pestic. Sci., 1977, (4), p. 2).
percutaneous LD50 for rats >3000, mice >5000 mg/kg. Toxicity Class EPA (formulation) IV
ECOTOXICOLOGY:
Fish TLm (72 h) >100 ppm. Daphnia LC50 (6 h) 40 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment DT50 in soil 27 d.
396 naproanilide
naptalam
Herbicide
O
C
NH
CO2H
HRACP WSSA 19; phthalamate

NOMENCLATURE:
naptalam
Common name NPA (JMAF, for sodium salt); alanap* (former exception, Turkey);
naptalame ((m) F-ISO); naptalam (BSI, E-ISO, WSSA)
IUPACname N-1-naphthylphthalamic acid
Chemical Abstracts name 2-[(1-naphthalenylamino)carbonyl]benzoic acid
CASRN[132661] naptalam; [132672] naptalam-sodium ECno2050734
(naptalam-sodium) SmilescodeOC(=O)c1ccccc1C(=O)Nc2cccc3ccccc23
PHYSICAL CHEMISTRY:
naptalam Mol. wt. 291.3 (naptalam); 313.3 (naptalam-sodium) M.f. C18H13NO3; sodium
salt C18H12NNaO3 Form Crystalline solid. M.p.185C V.p. <133 Pa (20C) Kow logP
= 0.104 (pH 5), 0.004 (pH 7), 0.036 (pH 9); logP = 0.006 (naptalam-sodium, Uniroyal,
via USDA ARS PPD) Henry <1.94 102 Pa m3 mol1 (calc.) S.g./density 1.36 (20C)
Solubility In water 200 mg/l (20C). In acetone 5, DMF 39, DMSO 43, methyl ethyl
ketone 4, isopropanol 2, carbon tetrachloride 0.1 (all in g/kg). Practically insoluble in
benzene, hexane, and xylene. Sodium salt: In water 300 g/kg (20C). In acetone 17, DMF
50, methyl ethyl ketone 6, isopropanol 21, benzene 0.5, xylene 0.4 (all in g/kg). Stability
Hydrolysis DT50 7.1 d (pH 5), 2.4 y (pH 7), stable (pH 9) (all 20C); a second study shows
DT50 2.9 d (pH 5, 25C). pKa 4.6
COMMERCIALISATION:
History Plant growth-regulating activity of N-arylphthalamic acids reported by O. L.
Hoffman & A. E. Smith (Science, 1949, 109, 588). Naptalam-sodium introduced by Uniroyal
Chemical Co., Inc. (became Chemtura Corp.) in 1955. Patents US 2556664; US 2556665
Manufacturers Chemtura
APPLICATIONS:
Biochemistry Inhibits indolylacetic acid transport. ModeofactionSelective herbicide,
absorbed predominantly by the roots, but also, to some extent, by the foliage, with
accumulation in meristematic tissue. Inhibits seed germination. Uses Pre-emergence
control of many broad-leaved weeds and some grasses in cucurbits, asparagus, peanuts,
soya beans, and established woody ornamentals, at 2.05.5 kg/ha. Phytotoxicity
Phytotoxic to beet, tomatoes, spinach, and lettuce. Formulation types GR; SL; WP.
naptalam 397
Compatibility Incompatible with pesticides which may cause amine transfer or

replacement.
PRODUCTS:
naptalam
Discontinued products Aksol* (DuPont); Alanap* (sodium salt) (Chemtura);
Alanap-L* (sodium salt) (Chemtura); Naptro* (Crystal).
ANALYSIS:
Product analysis by uv spectrometry; details from Chemtura. Residues determined by
hydrolysis to 1-naphthylamine, a derivative of which is measured by colorimetry (A. E.
Smith & G. M. Stone, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 4, 1). See also
Pestic. Anal. Man., II, 180.297. In soil, by hplc/ELCD (Environ. Chem. Methods).
naptalam
rabbits >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Inhalation LC50 (4 h)
for rats >2.07 mg/l air. NOEL In chronic feeding trials, NOEL for rats 30, dogs 5 mg/kg
b.w. daily. ADI/RfD (EPA) cRfD 0.258 mg/kg b.w. [2004]. Other Not a bacterial mutagen.
Toxicity Class WHO (a.i.) U EPA (formulation) II (Alanap-L) ECClassification Xn; R22
ECOTOXICOLOGY:
naptalam
Birds LD50 for mallard ducks >4640 mg/kg. Dietary LC50 (8 d) for mallard ducks and
bobwhite quail >10000 ppm. Fish LC50 (96 h) for rainbow trout 76.1, bluegill sunfish 354
ppm. Daphnia LC50 (48 h) 118.5 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, naptalam rapidly breaks down into phthalic acid and 1-naphthylamine.
Soil/Environment Duration of residual activity isc.38 w, depending on soil type
and moisture content (E. Smith et al., J. Agric. Food Chem., 1957, 5, 748). For sandy loam,
adsorption Kd 14.98, Koc 2152.
398 naptalam
natamycin
Fungicide
HO
O OH
O
CH3 O HO O
CO2H
O O CH3
OH
HO NH2
NOMENCLATURE:
Common name natamycin (BAN); pimaricin (traditional name); tennecetin (traditional
name)
IUPACname (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-
3,6-dideoxy--D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-
trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
Chemical Abstracts name [1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*
25R*,26S*)]-22-[(3-amino-3,6-dideoxy--D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-
methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-
carboxylic acid Other names myprozine CASRN[7681938] ECno2316835
SmilescodeCC1OC(OC2CC3OC(O)(CC(O)C3C(=O)O)CC(O)CC4OC4C=CC(=O)
OC(C)CC=CC=CC=CC=C2)C(O)C(N)C1O
PHYSICAL CHEMISTRY:
Composition Exists as a trihydrate. Tech. is >87%. Mol. wt. 665.7 (anhydrous)
M.f. C33H47NO13 Form White crystals. M.p.280300C (decomp.) Solubility In water
4.1 g/l (2022C). In DMSO >200, methanol 97, ethanol 5.5, acetone 0.85, petroleum spirit
0.1, benzene 0.05 (all in g/l, 2022C) (J. R. Marsh & P. J. Weiss, J. Assoc. Off. Anal. Chem., 1967,
50, 457). Stability Stable when dry, but sensitive to light. Forms water-soluble salts with
acids or alkalis.
COMMERCIALISATION:
Production By fermentation of Streptomyces natalensis and S. chattanoogensis.
History Structure established by B. T. Golding etal. (Tetrahedron Lett., 1966, p. 3551), W.
E. Meyer (Chem. Commun., 1968, p. 470) and G. Gaudiano etal. (Chem. Ind. (Milan), 1966,
48, 1327). Stereochemistry revised (J. M. Lancelin & J. M. Beau, J. Am. Chem. Soc., 1990, 112,
4060, 6749; A. J. Duplantier & S. Masamune, ibid., p. 7079). Introduced as a fungicide by
Gist-Brocades N.V. Patents GB 712547; GB 844289; US 3892850 Manufacturers Gist-
Brocades
natamycin 399
APPLICATIONS:
Uses Control of diseases of bulbs, especially basal rot (Fusarium oxysporum) of daffodils,
preferably combined with a hot-water treatment. Formulation types WP.
PRODUCTS:
Discontinued products Delvolan* (Gist-Brocades).
ANALYSIS:
Product analysis is either by bioassay with a suitable micro-organism, and confirmed by the
effect of the enzyme pimaricinase, or by uv spectrometry. Residues may be determined by
bioassay.
Oral Acute oral LD50 for rats 27304670 mg/kg (G. J. Levinskas, Toxicol. Appl. Pharmacol.,
1966, 8, 97). Skin and eye No acute toxicity, even at high doses. Not a skin or eye irritant
(rabbits). Not a skin sensitiser. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Fish Not toxic to fish.
ENVIRONMENTAL FATE:
Readily biodegradable.
NC-170
Insecticide
NOMENCLATURE:
IUPACname 4-chloro-5-(6-chloro-3-pyridylmethoxy)-2-(3,4-dichlorophenyl)pyridazin-
3(2H)-one
Chemical Abstracts name 4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-
dichlorophenyl)-3(2H)-pyridazinone CASRN[107360349]
DevelopmentcodesNC-170
SmilescodeClc1ccc(COc2cnn(c3ccc(Cl)c(Cl)c3)c(=O)c2Cl)cn1
PHYSICAL CHEMISTRY: Mol. wt. 417.1 M.f. C16H9Cl4N3O2 M.p.180181C
COMMERCIALISATION:
History Insect growth regulator reported by T. Miyake etal. (Proc. 1988 Br. Crop Prot. Conf. -
Pests Dis., 2, 535). Evaluated by Nissan Chemical Industries Ltd.
APPLICATIONS: Uses Evaluated for control of hoppers in rice.
LD50 for rabbits >2000 mg/kg. Not irritating to skin or eyes (rabbits).
ECOTOXICOLOGY:
Daphnia LC50 >1 mg/l.
400 NC-170
NC-196
Insecticide
NOMENCLATURE:
IUPACname 2-benzyl-5-[2-(ethoxycarbonylamino)ethoxy]-pyridazin-3(2H)-one
Chemical Abstracts name ethyl [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]
oxy]ethyl]carbamate CASRN[133456867] DevelopmentcodesNC-196
PHYSICAL CHEMISTRY: Mol. wt. 317.3 M.f. C16H19N3O4 M.p.73.578.0C
COMMERCIALISATION:
History Reported by T. Miyake etal. (Proc. Br. Crop Prot. Conf., Pests Dis. - 1994, 1, 59).
Manufacturers Nissan
APPLICATIONS:
ModeofactionJuvenile hormone mimic, also with ovicidal properties. Active by contact
and as a soil drench. Uses Evaluated for control of Brown planthopper (Nilaparvata
lugens) and diamond-back moth (Plutella xylostella) in rice. Formulation types GR .
1355 mg/kg. Skin and eye Acute percutaneous LD50 for female rabbits >5000 mg/kg. Slight
eye irritant, not a skin irritant (rabbits). Other Negative in Ames, micronucleus and Rec
tests.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp and rainbow trout >40 mg/l. Daphnia LC50 (48 h) >40 mg/l.
NC-330
Herbicide
CO2Me CH3
N
SO2NHCONH
N N N
N CH3
NOMENCLATURE:
IUPACname methyl 5-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl)-1-(2-pyridyl)
pyrazole-4-carboxylate
CASRN[104770298] DevelopmentcodesNC-330; NCI-851013 (both Nissan)
SmilescodeCOC(=O)c1cnn(c1S(=O)ONC(=O)Nc2nc(C)cc(C)n2)c3ccccn3
PHYSICAL CHEMISTRY: Mol. wt. 431.4 M.f. C17H17N7O5S Form Pale brownish solid.
M.p.159160C Solubility In water 849 mg/l (25C).
NC-330 401
COMMERCIALISATION:
History Herbicide reported by T. Nawamaki etal. (Proc. Br. Crop Prot. Conf. Weeds, 1991, 1,
45). Developed by Nissan Chemical Industries Ltd.
Manufacturers Nissan
APPLICATIONS:
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by
inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping
cell division and plant growth. Selectivity derives from rapid metabolism in the crop.
Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-
Food-Industry, 1995, 6, 914). ModeofactionSystemic herbicide, absorbed mainly by
the foliage and translocated to meristem tissues. Uses Control of grass and broad-leaved
weeds post-emergence in winter wheat, at 100150 g/ha. Phytotoxicity Phytotoxic to
winter barley.
ANALYSIS:
Residues of sulfonylureas in soil and water may be determined by immunoassay (Environ.
Chem. Methods). Methods for sulfonylurea residues in crops, soil and water reviewed (A. C.
Barefoot et al., Proc. Br. Crop Prot. Conf. Weeds, 1995, 2, 707).
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Non-irritating to skin;
mild eye irritant (rabbits). Other Non-mutagenic in the Ames test.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp >5 mg/l.
nickel bis(dimethyldithiocarbamate)
S
(CH3)2N C Ni
S
2
NOMENCLATURE:
IUPACname nickel bis(dimethyldithiocarbamate)
Chemical Abstracts name nickel dimethylcarbamodithioate Other names
organic nickel (JMAF) CASRN[15521650] DevelopmentcodesM-1; DDC-Ni
Smilescode[Ni+2].CN(C)C(=S)[S-].CN(C)C(=S)[S-]
PHYSICAL CHEMISTRY:
Composition Tech. is 96%. Mol. wt. 299.1 M.f. C6H12N2NiS4 Form Green, amorphous
powder. M.p.Decomposes above 250C Solubility Practically insoluble in water. In
402
nickel bis(dimethyldithiocarbamate)
chloroform 287, DMF 560, tetrahydrofuran 475 (all in mg/l, 20C). Stability Stable in
acidic and alkaline media at room temperature.
COMMERCIALISATION:
History Fungicide introduced by Mikasa Chemical Co. (who merged with Yashima
Chemical Industry Co. Ltd in 1996) and first registered in Japan in 1968.
Manufacturers Yashima
APPLICATIONS:
ModeofactionFoliar fungicide and bactericide with protective action. Uses Control of
bacterial leaf blight and bacterial grain rot in paddy rice, at 18002400 g/ha.
Formulation types DP; WP.
PRODUCTS:
Discontinued products Sankel* (Yashima).
EHC 78 (1988) is a general review of dithiocarbamates and their degradation products.
percutaneous LD50 for rats >5000 mg/kg. NOEL (2 y) for rats 200 mg/kg diet.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 360 mg/l.
nifluridide
Insecticide
NOMENCLATURE:
Common name nifluridide (BSI, ANSI, E-ISO, (m) F-ISO)
IUPACname 6-amino-,,,2,2,3,3-heptafluoro-5-nitropropion-m-toluidide
Chemical Abstracts name N-[2-amino-3-nitro-5-(trifluoromethyl)phenyl]-2,2,3,3-
tetrafluoropropanamide CASRN[61444620] DevelopmentcodesEL-468
SmilescodeNc1c(NC(=O)C(F)(F)C(F)F)cc(cc1[N+](=O)[O-])C(F)(F)F
COMMERCIALISATION:
History Insecticide evaluated by Eli Lilly & Co.
PRODUCTS:
Discontinued products Bant* (Lilly).
nifluridide 403
nipyraclofen
Herbicide
NOMENCLATURE:
Common name nipyraclof(ne) ((m) F-ISO); nipyraclofen (BSI, E-ISO)
IUPACname 1-(2,6-dichloro-,,-trifluoro-p-tolyl)-4-nitropyrazol-5-ylamine
Chemical Abstracts name 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitro-1H-
pyrazol-5-ylamine CASRN[99662110] DevelopmentcodesSLA 3992 (Bayer)
SmilescodeNc1c(cnn1c2c(Cl)cc(cc2Cl)C(F)(F)F)[N+](=O)[O-]
COMMERCIALISATION:
History Herbicide discovered by Bayer AG.
APPLICATIONS:
nithiazine
Insecticide
NO2
S CH
NH
IRAC4A
NOMENCLATURE:
Common name nithiazine (BSI, E-ISO, (m) F-ISO, ANSI, not Japan)
IUPACname 2-nitromethylene-1,3-thiazinane
Chemical Abstracts name tetrahydro-2-(nitromethylene)-2H-1,3-thiazine
CASRN[58842209] DevelopmentcodesIN-A0159 (DuPont); SD 35651 (Shell,
DuPont) Smilescode[O-][N+](=O)C=C1NCCCS1
PHYSICAL CHEMISTRY: Mol. wt. 160.2 M.f. C5H8N2O2S Solubility In water 200 g/l
(23C).
COMMERCIALISATION:
History Insecticide reported by S. B. Soloway etal. (Pestic.Venom Toxici. (Selected Papers
Internat. Congr. Entomol., 15th, 1976), 1978, p. 153). Notable as original member of
nitromethylene group of insecticides. Evaluated originally by Shell Research Ltd, later E. I.
du Pont de Nemours & Co.
APPLICATIONS:
Biochemistry Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the
insect central nervous system.
404 nithiazine
nitralin
Herbicide
NOMENCLATURE:
Common name nitralin (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPACname 4-methylsulfonyl-2,6-dinitro-N,N-dipropylaniline
Chemical Abstracts name 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzenamine
CASRN[4726141] DevelopmentcodesSD 11 831
SmilescodeCCCN(CCC)c1c(cc(cc1[N+](=O)[O-])S(=O)(=O)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Composition Tech. isc.94%. Mol. wt. 345.4 M.f. C13H19N3O6S Form Tech. is a yellow
powder. M.p.151152C (tech.) V.p. 0.002 mPa (25C) S.g./density 1.39 (20C, tech.)
Solubility In water 0.6 mg/l (22C). In acetone 360, DMSO 330, 2-nitropropane 250 (all
in g/l, 22C); sparingly soluble in common hydrocarbon and aromatic solvents and alcohols.
Stability Contact of nitralin with concentrated bases, or temperatures >200C, should
be avoided.
COMMERCIALISATION:
History Herbicide reported by J. B. Regan etal. (Proc. Northeast. Weed Control Conf.,
1966, p. 36). Introduced by Shell Research Ltd. Patents BE 672199
APPLICATIONS:
ModeofactionSelective herbicide. Uses Used pre-em. to control annual grasses and
many broad-leaved weeds in cotton, groundnuts, rape, soya beans and transplanted crops
such as brassicas, tobacco, tomatoes at 0.50.75 kg/ha on light soils, 1.01.5 kg/ha on
heavier soils (<5% o.m.); not used in highly organic or peat soils. Formulation types WP.
PRODUCTS:
Discontinued products Planavin* (Shell).
ANALYSIS:
Product analysis by i.r. spectrometry or by glc (Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 625). Residues determined by glc with ECD (ibid.).
LD50 for rabbits >2000 mg/kg. NOEL (2 y) for rats and dogs 2000 mg/kg diet.
ENVIRONMENTAL FATE:
Soil/Environment Relatively immobile in soil; DT50c.3050 d.
nitralin 405
nitrilacarb; nitrilacarb 1:1 zinc chloride complex

NOMENCLATURE:
Common name nitrilacarb (BSI, E-ISO, ANSI, ESA); nitrilacarbe ((m) F-ISO)
IUPACname 4,4-dimethyl-5-(methylcarbamoyloxyimino)valeronitrile; 4,4-dimethyl-5-
(methylcarbamoyloxyimino)pentanenitrile
Chemical Abstracts name 4,4-dimethyl-5-[[[(methylamino)carbonyl]oxy]imino]
pentanenitrile CASRN[29672193] nitrilacarb; [58270089] 1:1 complex with zinc
chloride, formerly [61332329] DevelopmentcodesAC82 258 (zinc complex); CL72
613 (nitrilacarb)
PHYSICAL CHEMISTRY:
Mol. wt. 197.2; (zinc chloride complex 333.5)
M.f. C9H15N3O2; (zinc chloride complex C9H15Cl2N3O2Zn) Form The tech. zinc chloride
complex is an almost colourless powder. M.p.120125C (zinc chloride complex) S.g./
density 0.5 (zinc chloride complex) Solubility The zinc chloride complex is soluble in
water, acetone, acetonitrile, alcohols; slightly soluble in chloroform; practically insoluble in
benzene, diethyl ether, hexane, toluene, xylene. Stability The zinc chloride complex is very
hygroscopic; stable 1.5 y (25C) when stored in original, unopened containers.
COMMERCIALISATION:
History Insecticide reported by W. K. Whitney & J. L. Aston (Proc. Br. Insectic. Fungic. Conf.,
8th, 1975, 2, 633). The 1:1 complex with zinc chloride introduced by American Cyanamid
Co. Patents US 3681505, US 3621049.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Nitrilacarb was used against a range of
phytophagous mites and aphids, also whiteflies, thrips, leafhoppers at 2575 g/100 l, and
Leptinotarsa decemlineata, at 0.5 kg/ha.
PRODUCTS:
Discontinued products Accotril* (1:1 zinc chloride complex.) (Cyanamid); Cyanotril*
(Cyanamid).
ANALYSIS:
Residues are determined by glc.
406
nitrilacarb; nitrilacarb 1:1 zinc chloride complex
nitrofen
Herbicide
NOMENCLATURE:
Common name NIP (JMAF); nitrofen (BSI, E-ISO, WSSA); nitrof(ne) ((m) F-ISO);
niclofen (Canada)
IUPACname 2,4-dichlorophenyl 4-nitrophenyl ether
Chemical Abstracts name 2,4-dichloro-1-(4-nitrophenoxy)benzene
CASRN[1836755] ECno2174060 DevelopmentcodesFW-925
Smilescode[O-][N+](=O)c1ccc(Oc2ccc(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 284.1 M.f. C12H7Cl2NO3 Form Crystalline solid.
M.p.7071C V.p. 1.06 mPa (40C) Solubility In water 0.71.2 mg/l (22C).
COMMERCIALISATION:
History Herbicide introduced by Rohm & Haas Co. Patents GB 974475; US 3080225
APPLICATIONS:
ModeofactionSelective herbicide. Uses Toxic to a number of broad-leaved and
grass weeds, and effective when left as a thin layer on the soil surface; activity is rapidly
lost on incorporation in soil. It was used for weed control in cereals pre-em. at 2 kg/
ha. Many vegetable crops tolerate applications pre-em. 3 kg/ha and post-em. 1 kg/ha.
PRODUCTS:
Discontinued products Tok* (Rohm & Haas); Tokkorn* (Rohm & Haas).
ANALYSIS:
Product analysis by glc with FID (I. L. Adler & B. M. Jones, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 403). Residues determined by glc with ECD of a derivative (idem, ibid.).
JMPR Evaln. 41 (1983). PDS 84 (1996). ICSC.929 (1999). IARC 30 (1983).
banned, 79/117/EEC as amended by 87/181/EEC.
IARC Class tech. is 2B
Oral Acute oral LD50 for rats 638888, rabbits 300510 (both as mg a.i. (as EC)/kg).
Skin and eye Neither the a.i. nor the formulations caused irritation to skin of rabbits or
visible toxic effects. ADI/RfD (JMPR) No ADI [1983]. Other Women of child-bearing age
should not be exposed to the product. Carcinogenic in rats and mice and is teratogenic
in several species tested. Toxicity Class WHO (a.i.) Ia ECClassification R45| R61| Xn;
R22| N; R50, R53
nitrofen 407
nitrofluorfen
Herbicide
NOMENCLATURE:
Common name nitrofluorfen (BSI, E-ISO, ANSI, WSSA); nitrofluorf(ne) ((m) F-ISO)
IUPACname 2-chloro-,,-trifluoro-p-tolyl 4-nitrophenyl ether
Chemical Abstracts name 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene
CASRN[42874011] DevelopmentcodesRH-2512
Smilescode[O-][N+](=O)c1ccc(Oc2ccc(cc2Cl)C(F)(F)F)cc1
PHYSICAL CHEMISTRY: Mol. wt. 317.7 M.f. C13H7ClF3NO3
COMMERCIALISATION:
History Herbicide evaluated by Rohm & Haas Co.
APPLICATIONS:
N-3-nitrophenylitaconimide
Fungicide
NOMENCLATURE:
IUPACname N-3-nitrophenylitaconimide
Chemical Abstracts name 3-methylene-N-(3-nitrophenyl)pyrrolidine-2,5-dione
CASRN[4137126] DevelopmentcodesB 720
Smilescode[O-][N+](=O)c1cccc(c1)N2C(=O)CC(=C)C2=O
PHYSICAL CHEMISTRY:
Mol. wt. 232.2 M.f. C11H8N2O4
COMMERCIALISATION:
History Fungicide reported by B. von Schmeling (Phytopathology, 1962, 52, 819). Evaluated
by Uniroyal Chemical Co., Inc.
4-(2-nitroprop-1-enyl)phenyl thiocyanate
Fungicide
NOMENCLATURE:
Common name nitrostyrene (JMAF)
IUPACname 4-(2-nitroprop-1-enyl)phenyl thiocyanate
Chemical Abstracts name 4-(2-nitro-1-propenyl)phenyl thiocyanate
CASRN[950005] SmilescodeCC(=Cc1ccc(SC#N)cc1)[N+](=O)[O-]
408
4-(2-nitroprop-1-enyl)phenyl thiocyanate
COMMERCIALISATION:
History Fungicide introduced by Nippon Kayaku Co., Ltd.
PRODUCTS:
Discontinued products Styrocide* (Nippon Kayaku).
norbormide
Rodenticide
NOMENCLATURE:
Common name nobormide ((f) F-ISO); norbormide (BSI, E-ISO, ANSI)
IUPACname 5-(-hydroxy--2-pyridylbenzyl)-7-(-2-pyridylbenzylidene)-8,9,10-
trinorborn-5-ene-2,3-dicarboximide
Chemical Abstracts name 3a,4,7,7a-tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-
8-(phenyl-2-pyridinylmethylene)-4,7-methano-1H-isoindole-1,3(2H)-dione
CASRN[991424] ECno2135896 DevelopmentcodesMcN-1025 (McNeil)
SmilescodeOC(C1=CC2C3C(C1C2=C(c4ccccc4)c5ccccn5)C(=O)NC3=O)(c6ccccc6)
c7ccccn7
PHYSICAL CHEMISTRY:
Composition Mixture of stereoisomers. Mol. wt. 511.6 M.f. C33H25N3O3
Form Colourless to off-white crystalline powder. M.p.>160C Solubility In water
60 mg/l (room temperature). In ethanol 14, chloroform >150, diethyl ether 1, 0.1M
hydrochloric acid 29 (all in mg/l, 30C). Stability Stable at room temperature when dry,
and to boiling water; hydrolysed by alkali.
COMMERCIALISATION:
History Rodenticide reported by A. P. Roszkowski etal. (Science, 1964, 144, 412).
Introduced by the McNeil Laboratories Inc. Patents GB 1059405
APPLICATIONS: Uses A selective rodenticide lethal to all members of the genus
Rattus that have been tested. It is relatively non-lethal to other rodents.
Formulation types CB .
PRODUCTS:
Discontinued products Raticate* (McNeil); Shoxin* (McNeil).
ANALYSIS:
Product analysis by uv spectrometry (C. A. Janick et al., J. Pharm. Sci., 1966, 55, 1077).
Oral Acute oral LD50 for Rattus rattus 52, R. norvegicus, R. hawaiiensisc.10, mice
2250, hamsters 140, prairie dogs >1000 mg/kg; a single oral dose of 1000 mg/kg had
no effect on cats, dogs, monkeys, nor was it lethal to any of 40 other animal species
tested (P. Roszkowski, J. Pharmacol. Exp. Ther., 1965, 149, 288). NOEL Three adult male
norbormide 409
volunteers received 15 mg/kg daily for 3 d without ill-effect. Toxicity Class WHO (a.i.) II
nornicotine
Insecticide
NOMENCLATURE:
Common name nornicotine (traditional name)
IUPACname (S)-3-(pyrrolidin-2-yl)pyridine
Chemical Abstracts name (S)-3-(2-pyrrolidinyl)pyridine CASRN[494973]
SmilescodeC1CNC(C1)c2cccnc2
PHYSICAL CHEMISTRY:
Mol. wt. 148.2 M.f. C9H12N2
COMMERCIALISATION:
noruron
Herbicide
For stereochemistry, see W. R. Diveley et al., J. Org. Chem., 34, 616 (1969).
NOMENCLATURE:
Common name norea (ANSI, WSSA); noruron (BSI, E-ISO, (m) F-ISO)
IUPACname (3aRS,4SR,5RS,7SR,7aRS)-1,1-dimethyl-3-(perhydro-4,7-methanoinden-5-yl)
urea; (3aRS,4SR,5RS,7SR,7aRS)-3-(hexahydro-4,7-methanoindan-5-yl)-1,1-dimethylurea
Chemical Abstracts name 3a,4,5,7,7a-N,N-dimethyl-N-(octahydro-4,7-methano-
1H-inden-5-yl)urea CASRN[18530568] 3a,4,5,7,7a- isomer; [2163793]
unstated stereochemistry DevelopmentcodesHercules 7531
SmilescodeCN(C)C(=O)NC1CC2CC1C3CCCC23
PHYSICAL CHEMISTRY:
Mol. wt. 222.3 M.f. C13H22N2O
COMMERCIALISATION:
History Herbicide reported by G. A. Buntin etal. (Abstr. Am. Chem. Soc. Meeting, Los
Angeles, 1963). Introduced by Hercules Inc., Agrochemical Div. (and later Nor-Am.).
APPLICATIONS:
ModeofactionSelective herbicide.
PRODUCTS:
Discontinued products Herban* (Hercules).
410 noruron

nuarimol
Fungicide
OH
N
F C
N
Cl
FRAC3, G1; SBI Class I, DMI: pyrimidine

NOMENCLATURE:
Common name nuarimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname ()-2-chloro-4-fluoro--(pyrimidin-5-yl)benzhydryl alcohol
Chemical Abstracts name ()--(2-chlorophenyl)--(4-fluorophenyl)-5-
pyrimidinemethanol CASRN[63284719] unstated stereochemistry ECno2640711
DevelopmentcodesEL-228 (Lilly) SmilescodeOC(c1ccc(F)cc1)(c2cncnc2)c3ccccc3Cl
PHYSICAL CHEMISTRY:
Mol. wt. 314.7 M.f. C17H12ClFN2O Form Colourless crystals. M.p.126127C V.p.
<0.0027 mPa (25C) Kow logP = 3.18 (pH 7)
Henry 6.73 108 Pa m3 mol1 (calc.) S.g./density 0.60.8 (bulk) Solubility In water 26
mg/l (pH 7, 25C). In acetone 170, methanol 55, xylene 20 (all in g/l, 25C). Readily soluble
in acetonitrile, benzene, and chloroform. Slightly soluble in hexane. Stability Decomposed
rapidly by uv light. Stable at 52C.
COMMERCIALISATION:
History Fungicide introduced in Greece (1980) by Eli Lilly & Co. (agrochemical interests
later Dow AgroSciences). Rights sold to Gowan Co. Patents GB 1218623
APPLICATIONS:
Biochemistry Sterol demethylation (ergosterol biosynthesis) inhibitor.
ModeofactionSystemic foliar fungicide with curative and protective action. Interferes
with the completion of division of sporids. Uses Control of a wide range of pathogenic
fungi, such as Pseudocercosporella spp., Septoria spp., Ustilago spp., powdery mildew, leaf
spot, etc., in cereals, both as a foliar spray and as a seed treatment; powdery mildews
on pome fruit, stone fruit, vines, hops, cucurbits, and other crops; scab on apples; etc.
Formulation types EC; SC. SL; WP; Seed treatment.
nuarimol 411
PRODUCTS:
Discontinued products Cidorel* (BASF Espaola); Gandural* (Dow AgroSciences);
Gauntlet* (Shell); Tridal* (Dow AgroSciences); Trimidal* (Dow AgroSciences); Triminol*
(DowElanco); Discontinuedmixtures Gandural S* (+sulfur) (Dow AgroSciences).
ANALYSIS:
Product analysis by glc with FID (E. W. Day & O. D. Decker, Anal. Methods Pestic. Plant Growth
Regul., 1984, 13, 183). Residues in soil and plant tissue determined by glc with ECD (idem,
ibid.). Details available from Dow AgroSciences.
3000, beagle dogs 500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000
mg/kg. No skin irritation; slight eye irritant (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation Rats essentially unaffected after 1 h by 0.37 mg tech./l air. NOEL (2 y) for rats
and mice 50 mg/kg diet. Toxicity Class WHO (a.i.) III EPA (formulation) III
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 200 mg/kg. Fish LC50 (96 h) for bluegill
sunfishc.12.1 mg/l. Daphnia LC50 (48 h) >25 mg/l. Algae EC50 (96 h) for Selenastrum
capricornutum 2.5 mg/l. Bees Not toxic to bees; LC50 (contact) >11 g/l. Worms NOEC
(14 d) for earthworms 100 g/kg soil.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, elimination is rapid. Plants Numerous
photodegradation products are formed. Soil/Environment Microbial degradation is
accelerated by light; DT50 (lab.) 344 d, (field)c.150 d. Koc 26, depending on soil type.
OCH
Fungicide, herbicide
NOMENCLATURE:
Common name OCH (WSSA)
IUPACname octachlorocyclohex-2-enone
Chemical Abstracts name 2,3,4,4,5,5,6,6-octachloro-2-cyclohexen-1-one
CASRN[4024811] SmilescodeClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C1=O
PHYSICAL CHEMISTRY:
Mol. wt. 371.7 M.f. C6Cl8O
COMMERCIALISATION:
History Herbicide and fungicide introduced by Goodrich Chemical Co.
412 OCH
PRODUCTS:
Discontinued products Oktone* (Goodrich).
OCS 21693
Herbicide
NOMENCLATURE:
IUPACname methyl 2,3,5,6-tetrachloro-N-methoxy-N-methylterephthalamate
Chemical Abstracts name methyl 2,3,5,6-tetrachloro-4-[[methoxy(methyl)amino]
carbonyl]benzoate CASRN[14419013] DevelopmentcodesOCS 21693
SmilescodeCON(C)C(=O)c1c(Cl)c(Cl)c(C(=O)OC)c(Cl)c1Cl
COMMERCIALISATION:
History Herbicidal activity reported by W. Furness (Symp. New Herbic., 3rd, 1969, p. 261).
Introduced by Velsicol Corp. (later Sandoz AG).
2-(octylthio)ethanol
Insect repellent
CH3(CH2)7SCH2CH2OH
NOMENCLATURE:
IUPACname 2-(octylthio)ethanol
Chemical Abstracts name 2-(octylthio)ethanol Other names 2-hydroxyethyl octyl
sulfide CASRN[3547339] ECno2225984 DevelopmentcodesPhillips R-874
SmilescodeCCCCCCCCSCCO
PHYSICAL CHEMISTRY: Mol. wt. 190.3 M.f. C10H22OS Form Pale amber liquid,
with a mild, mercaptan-like odour. M.p.0C B.p. 98C /0.1 mmHg V.p. 79 mPa (25C)
Kow logP = 0.561 S.g./density 0.9250.935 (24C) Solubility Slightly soluble in water;
miscible with most organic solvents including refined kerosene, though a co-solvent
such as isopropanol is required with the latter to maintain solution at low temperatures.
Stability Stable at pH 68, and to heat and light.
COMMERCIALISATION:
History Insect-repelling properties reported by L. D. Goodhue (J. Econ. Entomol., 1960,
53, 805). Introduced by Phillips Petroleum Co. and by the McLaughlin Gormley King Co.
Patents US 2863799 (to Phillips Petroleum Co., 1958) Manufacturers MGK
APPLICATIONS: Uses Its chief use is as a repellent to Blattodea, at 1 g/m{2}. Also as
a repellent using pressurised patio foggers against Formicidae, Muscidae and crawling
insects. Formulation types EC; OL .
2-(octylthio)ethanol 413
ANALYSIS:
Details of a glc method available from McLaughlin Gormley King Co.
albino rabbits 13590 mg/kg. Application of 0.05 mg to the cornea of albino rats produced
corneal necrosis in 2 of the 5 eyes tested, but they healed without opacities.
Inhalation LC50 (4 h) for rats 6.12 mg/l. NOEL In 90 d feeding trials, rats receiving 20000
mg/kg diet showed no adverse effect. Toxicity Class WHO (a.i.) U.
ECClassification Xi; R41
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout 2.9, bluegill sunfish 2.7 mg/l. Daphnia LC50 (48 h)
0.38 mg/l.
oxapyrazon; oxapyrazon-sodium;
oxapyrazon-(2-hydroxyethyldimethylammonium)
Herbicide
NOMENCLATURE:
Common name oxapyrazon* (BSI (19841990), E-ISO (pre-1990), for
2-hydroxyethyldimethylammonium salt); oxapyrazone ((f) F-ISO); oxapyrazon (Canada,
since 1990 BSI, E-ISO)
IUPACname 5-bromo-1,6-dihydro-6-oxo-1-phenylpyridazin-4-yloxamic acid
Chemical Abstracts name [(5-bromo-1,6-dihydro-6-oxo-1-phenyl-4-pyridazinyl)
amino]oxoacetic acid CASRN[4489310] oxapyrazon; [25316567]
oxapyrazon-sodium; [25316578] oxapyrazon-(2-hydroxyethyldimethylammonium)
DevelopmentcodesBAS 3380H (oxapyrazon-sodium); BAS 350H (oxapyrazon-(2-
hydroxyethyldimethylammonium)) (both BASF)
Smilescodeoxapyrazon-sodium:[Na+].[O-]C(=O)C(=O)Nc1cnn(c2ccccc2)c(=O)c1Br
PHYSICAL CHEMISTRY:
Mol. wt. 338.1; (sodium salt 360.1; 2-hydroxyethyldimethylammonium salt 427.3)
M.f. C12H8BrN3O4; (sodium salt C12H7BrN3NaO4; 2-hydroxyethyldimethylammonium salt
C16H19BrN4O5)
COMMERCIALISATION:
History Herbicide developed by BASF AG.
414
oxapyrazon; oxapyrazon-sodium; oxapyrazon-(2-hydroxyethyldimethylammonium)
oxathiapiprolin
Fungicide
CF3
O N
F
N
N
N C H3
F
O
N S
NOMENCLATURE:
Common name oxathiapiprolin (pa ISO)
IUPACname 1-(4-{4-[(5RS)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-
thiazol-2-yl}-1-piperidyl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone
Chemical Abstracts name 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-
isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-
1-yl]ethanone CASRN[1003318679] DevelopmentcodesDPXQGU42
SmilescodeCc1cc(nn1CC(=O)N2CCC(CC2)c3nc(cs3)C4=NOC(C4)c5c(cccc5F)F)C(F)(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 539.52 M.f. C24H22F5N5O2S
oxydeprofos
IRAC1B
NOMENCLATURE:
Common name oxyd(profos) ((m) F-ISO); oxydeprofos (BSI, E-ISO); ESP (JMAF)
IUPACname S-2-ethylsulfinyl-1-methylethyl O,O-dimethyl phosphorothioate
Chemical Abstracts name S-[2-(ethylsulfinyl)-1-methylethyl] O,O-dimethyl
phosphorothioate CASRN[2674911] DevelopmentcodesBayer 23 655; S 410
SmilescodeCCS(=O)CC(C)SP(=O)(OC)OC
PHYSICAL CHEMISTRY: Mol. wt. 260.3 M.f. C7H17O4PS2 Form Yellow oil.
B.p. 115C /0.02 mmHg V.p. 0.625 mPa (20C) S.g./density 1.257 (20C)
Solubility Soluble in water, alcohols, chlorinated hydrocarbons, ketones; sparingly soluble
in light petroleum.
COMMERCIALISATION:
History Insecticide described by G. Schrader (Phosphorsure-Ester). Introduced by Bayer
AG. Patents DE 1035958; US 2952700
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic and contact
insecticide and acaricide. Uses Effective against sap-feeding insects and mites at 25 g/100 l.
oxydeprofos 415

PRODUCTS:
Discontinued products Estox* (Bayer); Metasystox S* (Bayer).
ANALYSIS:
Product analysis is by titration after reduction by titanium disulfate. Residues may be
determined by glc.
Oral Acute oral LD50 for rats 105 mg/kg. Skin and eye Acute percutaneous LD50 for male
rats 800 mg/kg. NOEL In 50 d feeding trials, the growth of rats receiving 10 mg/kg daily
was not affected. Other I.p. LD50 for guinea-pigs 100 mg/kg. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp and Japanese killifish >40 mg/l.
oxydisulfoton
IRAC1B
NOMENCLATURE:
Common name oxydisulfoton (BSI, E-ISO, (m) F-ISO)
IUPACname O,O-diethyl S-2-ethylsulfinylethyl phosphorodithioate
Chemical Abstracts name O,O-diethyl S-[2-(ethylsulfinyl)ethyl] phosphorodithioate
CASRN[2497076] ECno2196791
DevelopmentcodesBayer 23 323; S 309; L 16/184
SmilescodeCCOP(=S)(OCC)SCCS(=O)CC
COMMERCIALISATION:
History Insecticide and acaricide introduced by Bayer AG.
APPLICATIONS:
acaricide.
PRODUCTS:
Discontinued products Disyston S* (Bayer).
Toxicity Class WHO (a.i.) O ECClassification T+; R28| T; R24| N; R50, R53| concn.
dep.
416 oxydisulfoton
parafluron
Herbicide
NOMENCLATURE:
Common name parafluron (BSI, E-ISO, (m) F-ISO)
IUPACname 1,1-dimethyl-3-(,,-trifluoro-p-tolyl)urea
Chemical Abstracts name N,N-dimethyl-N-[4-(trifluoromethyl)phenyl]urea
CASRN[7159991] DevelopmentcodesC 15 935
SmilescodeCN(C)C(=O)Nc1ccc(cc1)C(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 232.2 M.f. C10H11F3N2O
COMMERCIALISATION:
History Herbicide introduced by Ciba AG (later Ciba-Geigy AG).
pebulate
Herbicide
CH3(CH2)3 S (CH2)2CH3
N C
CH3CH2 O
HRACN WSSA 8; thiocarbamate
NOMENCLATURE:
Common name pebulate (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPACname S-propyl butyl(ethyl)thiocarbamate
Chemical Abstracts name S-propyl butylethylcarbamothioate CASRN[1114712]
ECno2142154 DevelopmentcodesR-2061 (Stauffer)
SmilescodeCCCCN(CC)C(=O)SCCC
PHYSICAL CHEMISTRY:
Composition Tech. material is 95% pure. Mol. wt. 203.3 M.f. C10H21NOS
Form Colourless or yellow liquid, with an aromatic odour. B.p. 142C /21 mmHg
V.p. 9 Pa (30C); 4.7 Pa (25C) Kow logP = 3.83 Henry 20 Pa m3 mol1 (20C, calc.)
S.g./density 0.956 (20C) Solubility In water 60 mg/l (20C). Miscible with most
organic solvents, e.g. acetone, benzene, toluene, xylene, methanol, isopropanol and
kerosene. Stability Stable up to 200C. In water, DT50 (40C) 11 d (pH 4 and pH 10),
12 d (pH 7). F.p. 124C
COMMERCIALISATION:
History Herbicide reported by E. O. Burt (Proc. South. Weed Conf., 12th, 1959, p. 19).
pebulate 417
Introduced by Stauffer Chemical Co. (now Syngenta AG). Divested to Cedar Chemical
Corp. in 2001. Patents US 3175897
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). The sulfoxide may be the
active form (P. B. Barrett & J. L. Harwood, Proc. Br. Crop Prot. Conf. Weeds, 1993, 1, 183).
ModeofactionSelective systemic herbicide, absorbed by the roots, with translocation
throughout the plant. Acts by inhibition of germination. Uses Control of annual grasses
(including nutgrasses) and some broad-leaved weeds in sugar beet, tomatoes and tobacco.
Applied pre-emergence, at 46 kg/ha with soil incorporation. Formulation types EC; GR.
PRODUCTS:
Discontinued products Tillam* (Tri-Ag); Discontinuedmixtures Edge* (+fonofos)
(Zeneca).
ANALYSIS:
Product analysis by glc with FID (AOACMethods, 18th Ed., 974.05; CIPACHandbook, 1983,
1B, 1887). Residues in crops and soils determined by glc (G. G. Patchett et al., Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 343; W.Y. Ja et al., Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 698). See also Pestic. Anal. Man., II, 180.238. In soil or water by glc
with NPD (AOACMethods, 18th Ed., 991.07; Environ. Chem. Methods). Analytical methods
available from Syngenta.
EHC 76 (1988); a general review of thiocarbamates. EU Status (1107/2009) Not
LD50 for rabbits 4640 mg/kg. Slight irritation of skin, eyes and mucous membranes (rabbits).
Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for female rats >3.5 mg/l.
NOEL (2 y) for rats 0.74 mg/kg b.w. daily (EPA RED). Not carcinogenic or teratogenic.
ADI/RfD (EPA) aRfD 0.5, cRfD 0.007 mg/kg b.w. [1999]. Toxicity Class WHO (a.i.) II EPA
(formulation) III ECClassification Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Birds Dietary LC50 (7 d) for bobwhite quail 8400 mg/kg diet. Fish LC50 (96 h) for rainbow
trout and bluegill sunfishc.7.4 mg/l; (48 h) for silver mullet 6.25, killifish 7.78 mg/l.
Daphnia LC50 (48 h) 5.9 mg/l. Bees Non-toxic to bees at 0.011 mg/bee.
ENVIRONMENTAL FATE:
Animals In animals, pebulate is rapidly metabolised. In rats, following oral
administration,c.50% was expired as CO2, 25% excreted in the urine, and 5% excreted
in the faeces, within 3 days. Plants In plants, pebulate is rapidly metabolised to CO2 and
naturally-occurring plant constituents. Soil/Environment In soil, pebulate disappears
mainly by microbial degradation to the mercaptan, ethylbutylamine and CO2. DT50 in soil
23 w.
418 pebulate
penfluron
Insecticide
benzoylurea
NOMENCLATURE:
IUPACname 1-(2,6-difluorobenzoyl)-3-(,,-trifluoro-p-tolyl)urea
Chemical Abstracts name 2,6-difluoro-N-[[[4-(trifluoromethyl)phenyl]amino]carbonyl]
benzamide CASRN[35367318] DevelopmentcodesPH-60-44 (Duphar); TH-60-44
(Thompson-Hayward)
COMMERCIALISATION:
History Evaluated by Duphar B.V. and Thompson-Hayward Chemical Co.; EUP granted in
1983 (Shibuya).
APPLICATIONS: Uses Evaluated against spruce budworm. Effective against pests of
stored products, such as Tribolium castaneum and Trogoderma granarium.
pentanochlor
Herbicide
CH3
CH3 NHCOCH(CH2)2CH3
Cl
HRACC2 WSSA 7; anilide

NOMENCLATURE:
Common name pentanochlor (BSI, E-ISO); CMMP (JMAF); pentanochlore ((f) F-ISO);
solan (WSSA, Canada, ex ANSI)
IUPACname 3-chloro-2-methylvalero-p-toluidide
Chemical Abstracts name N-(3-chloro-4-methylphenyl)-2-methylpentanamide
SmilescodeCCCC(C)C(=O)Nc1ccc(C)c(Cl)c1
PHYSICAL CHEMISTRY: Mol. wt. 239.7 M.f. C13H18ClNO Form Colourless solid;
(tech., colourless to pale cream powder). M.p.8586C (pure); 8286C (tech.)
V.p. Very low at room temperature S.g./density 1.106 (20C) Solubility In water
89 mg/l (20C). In diisobutyl ketone 460, isophorone 550, methyl isobutyl ketone 520,
xylene 200300, pine oil 410 (all in g/kg, 20C). Stability Stable to hydrolysis in neutral
media at room temperature.
pentanochlor 419
COMMERCIALISATION:
History Herbicide reported by D. H. Moore (Proc. Northeast. Weed Control Conf., 1960,
p. 86). Introduced by FMC Corp. Patents GB 869169; US 3020142
APPLICATIONS:
site. ModeofactionSelective, contact herbicide with absorption via the leaves.
Uses Selective pre- and post-emergence herbicidal control in carrots, celeriac, celery,
fennel, parsley, and parsnips, at <4 kg/ha. Used pre-sowing on tomatoes and some flower
crops, and as a contact spray in carnations, chrysanthemums, fruit trees, ornamental trees
and shrubs, roses, sweet peas, and tomatoes. With chlorpropham, used as above, though
also on narcissi and tulips. Formulation types EC.
PRODUCTS:
Discontinued products Croptex Bronze* (Certis UK); Solan* (Nufarm UK);
Discontinuedmixtures Atlas Brown* (+chlorpropham) (Nufarm UK).
ANALYSIS:
Residues determined by hydrolysis to 3-chloro-p-toluidine which is estimated by glc.
Oral Acute oral LD50 for rats >10000 mg/kg. Skin and eye Slight irritation of skin and
mucous membranes. NOEL In 140 d feeding trials, rats receiving 20000 mg/kg diet
suffered no effect on body weight or survival, but histopathological changes were found in
the liver; these effects were not observed at 2000 mg/kg diet. Toxicity Class WHO (a.i.)
U EPA (formulation) IV
ECOTOXICOLOGY:
Bees Not very toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Similar to 3,4-dichloroaniline-based acylanilide herbicides; converted
to 3-chloro-4-methylaniline. This does not accumulate but is converted to 3,3-dichloro-
4,4-dimethylazobenzene.
perfluidone
Herbicide
NOMENCLATURE:
Common name perfluidone (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 1,1,1-trifluoro-N-(4-phenylsulfonyl-o-tolyl)methanesulfonamide;
1,1,1-trifluoro-2-methyl-4-(phenylsulfonyl)methanesulfonanilide
Chemical Abstracts name 1,1,1-trifluoro-N-[2-methyl-4-(phenylsulfonyl)
420 perfluidone
phenyl]methanesulfonamide CASRN[37924133] ECno2537183

DevelopmentcodesMBR-8251
SmilescodeCc1cc(ccc1NS(=O)(=O)C(F)(F)F)S(=O)(=O)c2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 379.4 M.f. C14H12F3NO4S2 Form Colourless crystals. M.p.142144C V.p.
<1.3 mPa (25C) Solubility In water 60 mg/l (22C). In acetone 750, methanol 595,
acetonitrile 560, chloroform 175, dichloromethane 162, diethyl ether 93, benzene 11,
hexane 0.03 (all in g/l, 22C). Stability Stable to both acid and alkaline hydrolysis, and to
heat. Susceptible to slow degradation in aqueous solution under uv irradiation. pKa 2.5
COMMERCIALISATION:
History Herbicide reported by W. A. Gentner (Agric. Res. (Wash., D.C.), 1971, 20(2), 5).
Introduced by 3M Company. Patents GB 1306564; BE 765558
APPLICATIONS:
Biochemistry Interferes with protein biosynthesis and with cellular respiration.
ModeofactionSelective herbicide which acts by contact and by root absorption.
Uses Pre-emergence herbicide for control of Cyperus esculentus, many
monocotyledonous weeds, and certain broad-leaved weeds in cotton, transplanted
tobacco, rice, sugar cane, and established turf at 1.14.5 kg/ha. Phytotoxicity Phytotoxic
to carrots, oats, sugar beet, soya beans, and spinach. Formulation types WP; GR; SL .
Compatibility Incompatible with liquid nitrogen fertilisers and acidic fertilisers.
PRODUCTS:
Other mixtures Destun* (+benazolin) (3M).
ANALYSIS:
Product analysis by glc of a derivative with FID (C. D. Green, Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 437). Residues determined by glc of a derivative with ECD (idem,
ibid.).
LD50 for rabbits >4000 mg/kg. Severe eye irritant; mild skin irritant (rabbits).
Inhalation LC50 (4 h) for rats 3.2 mg/l air. NOEL In 90 d feeding trials, rats receivingc.800
mg/kg diet and dogs receivingc.200 mg/kg showed no ill effects. ADI/RfD (EPA) 0.01 mg/
kg b.w. [1989]. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification Xn;
R22| Xi; R36
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for quail 7144, ducks >10000 mg/kg (for WP formulation).
Fish LC50 (96 h) for rainbow trout 312, bluegill sunfish 318 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment In wet, neutral or alkaline soils, leaching occurs, particularly in soils
perfluidone 421
having low clay or organic matter content. Leaching occurs to a much lesser extent
in acidic soils. Microbial action accounts for the breakdown of a significant portion of
perfluidone in the soil, although photodecomposition and volatilisation also occur to some
extent. Soil DT50c.1 month.
PH 60-38
Insecticide
IRAC15
NOMENCLATURE:
IUPACname 1-(4-chlorophenyl)-3-(2,6-dichlorobenzoyl)urea
Chemical Abstracts name 2,6-dichloro-N-[[(4-chlorophenyl)amino]carbonyl]benzamide
CASRN[35409973] DevelopmentcodesPH 60-38
SmilescodeClc1ccc(NC(=O)NC(=O)c2c(Cl)cccc2Cl)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 343.6 M.f. C14H9Cl3N2O2
COMMERCIALISATION:
History Insect growth regulator evaluated by Philips Duphar (later Uniroyal Chemical Co.,
Inc.).
APPLICATIONS:
Biochemistry Chitin synthesis inhibitor. ModeofactionInsect growth regulator
phenisopham
Herbicide
NOMENCLATURE:
Common name ph(nisophame) ((m) F-ISO); phenisopham (BSI, E-ISO)
IUPACname isopropyl 3-[ethyl(phenyl)carbamoyloxy]carbanilate;
3-(isopropoxycarbonylamino)phenyl N-ethylcarbanilate
Chemical Abstracts name 3-[[(1-methylethoxy)carbonyl]amino]phenyl
ethylphenylcarbamate CASRN[57375630] DevelopmentcodesSN 58 132
(Schering) SmilescodeCCN(C(=O)Oc1cccc(NC(=O)OC(C)C)c1)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 342.4 M.f. C19H22N2O4 Form Colourless solid.
M.p.109110C V.p. 6.65 104 mPa (25C) Henry 7.59 105 Pa m3 mol1 (calc.)
Solubility In water 3 mg/l (25C). In dichloromethane 300, ethanol 98, methanol 60,
isopropanol 26, toluene 35 (all in g/l, 25C). Stability Unstable under alkaline conditions,
DT50 35 d (pH 9), 29 d (pH 12), 2 d (pH 13), 7 h (pH 14).
COMMERCIALISATION:
History Herbicide reported in Schering AG Tech. Inf. 1977. Introduced by Schering AG.
Patents DE 2413933
422 PH 60-38
APPLICATIONS:
ModeofactionSelective and contact herbicide. It acts mainly by contact but there also
appears to be some activity through the soil. Uses Mainly used to control broad-leaved
weeds in cotton; applied at 12 kg/ha. Formulation types EC.
PRODUCTS:
Discontinued products Diconal* (Schering); Verdinal* (Schering).
ANALYSIS:
Product analysis by tlc. Residues determined by hydrolysis to N-ethylaniline a derivative
being measured by glc with ECD.
percutaneous LD50 for rabbits >1000 mg/kg. NOEL (90 d) for rats 1 mg/kg daily; (182 d)
for dogs 3 mg/kg daily. Toxicity Class WHO (a.i.) U
phenkapton
IRAC1B
NOMENCLATURE:
Common name phenkapton (BSI, E-ISO, (m) F-ISO); CMP (JMAF)
IUPACname S-2,5-dichlorophenylthiomethyl O,O-diethyl phosphorodithioate
Chemical Abstracts name S-[[(2,5-dichlorophenyl)thio]methyl] O,O-diethyl
phosphorodithioate CASRN[2275141] ECno2188927
DevelopmentcodesG 28 029 SmilescodeCCOP(=S)(OCC)SCSc1cc(Cl)ccc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 377.3 M.f. C11H15Cl2O2PS3
COMMERCIALISATION:
History Insecticide and acaricide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
Toxicity Class WHO (a.i.) O ECClassification T; R23/24/25| N; R50, R53
phenkapton 423
phenmedipham-ethyl
Herbicide
NOMENCLATURE:
Common name phenm(diphame-) ((m) F-ISO); phenmedipham-ethyl (BSI, E-ISO)
IUPACname 3-ethoxycarbonylaminophenyl 3-methylcarbanilate; ethyl
3-(3-methylcarbaniloyloxy)carbanilate
Chemical Abstracts name 3-[(ethoxycarbonyl)amino]phenyl (3-methylphenyl)
carbamate CASRN[13684441] DevelopmentcodesSN 38 574
SmilescodeCCOC(=O)Nc1cccc(OC(=O)Nc2cccc(C)c2)c1
PHYSICAL CHEMISTRY:
Mol. wt. 314.3 M.f. C17H18N2O4
COMMERCIALISATION:
History Superseded ethyl homologue of phenmedipham. Herbicide evaluated by Schering
AG.
APPLICATIONS:
site.
phenobenzuron
Herbicide
NOMENCLATURE:
Common name phenobenzuron (BSI, E-ISO, (m) F-ISO)
IUPACname 1-benzoyl-1-(3,4-dichlorophenyl)-3,3-dimethylurea
Chemical Abstracts name N-(3,4-dichlorophenyl)-N-[(dimethylamino)carbonyl]
benzamide CASRN[3134121] DevelopmentcodesPP 6525
SmilescodeCN(C)C(=O)N(C(=O)c1ccccc1)c2ccc(Cl)c(Cl)c2
COMMERCIALISATION:
History Herbicidal activity reported by P. Poignant etal. (Symp. New Herbic., 2nd, 1965, p.
1). Introduced by Pechiney-Progil (later Rhne-Poulenc Agrochimie).
PRODUCTS:
Discontinued products Benzomarc* (Rhne-Poulenc).
424 phenobenzuron
2-phenyl-4H-3,1-benzoxazin-4-one
Herbicide
NOMENCLATURE:
IUPACname 2-phenyl-4H-3,1-benzoxazin-4-one (I)
Chemical Abstracts name (I) CASRN[1022464] DevelopmentcodesH-170
SmilescodeO=c1oc(nc2ccccc12)c3ccccc3
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Meded. Landbouwhogesch. Opzoekingsstn. Staat
Gent, 1965, 30, 163). Introduced by BASF AG.
PRODUCTS:
Discontinued products Linurotox* (BASF).
phenylmercury chloride
Fungicide
NOMENCLATURE:
IUPACname phenylmercury chloride
Chemical Abstracts name chlorophenylmercury CASRN[100561]
PHYSICAL CHEMISTRY:
Mol. wt. 313.1 M.f. C6H5ClHg Form Colourless crystals. M.p.250C V.p. 1.3 10-2
mPa (0C); 1.3 mPa (45C) Solubility In water 0.003%. Readily soluble in acetone,
cyclohexanone, methyl ethyl ketone, tetrahydrofuran, DMF. Slightly soluble in benzene,
toluene, xylene, chloroform, methanol, ethanol (room temperature). Sparingly soluble in
carbon tetrachloride, diethyl ether, petroleum ether and mineral oils. Stability Stable
under neutral conditions. Weak alkalis convert it to phenylmercury hydroxide, strong
alkalis to the oxide. Stable in acidic media at room temperature.
COMMERCIALISATION:
Manufacturers Arco Chemie; Bayer; ICI; Steetley
APPLICATIONS:
ModeofactionCurative fungicide. Uses Dry fungicidal treatment for the protection of
seed (wheat, rye, barley, and oats) against Stinking smut, snow mould and barley leaf stripe.
PRODUCTS:
Discontinued products Agronal* (Spolana); Discontinuedmixtures Tillantox*
(+benquinox) (Bayer).
phenylmercury chloride 425

ANALYSIS:
973.11). Mercury impurities determined (CIPACHandbook, 1994, F, 264).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. JMPR Evaln.
9 (1967). EU Status (1107/2009) Aryl mercury compounds considered to be outside the
scope of the Directive; already banned, 79/117/EEC.
Oral Acute oral LD50 for highly soluble organic mercury compounds 50100 mg/kg.
Skin and eye Causes irritation of skin, mucous membranes and respiratory organs.
ADI/RfD (JMPR) No ADI [1967]. PIC Yes.
phenylmercury dimethyldithiocarbamate
Fungicide
NOMENCLATURE:
IUPACname phenylmercury dimethyldithiocarbamate
Chemical Abstracts name (dimethylcarbamodithioato-S,S)phenylmercury
CASRN[32407991] SmilescodeCN(C)C(=S)[S-].[Hg+]c1ccccc1
PHYSICAL CHEMISTRY: Mol. wt. 397.9 M.f. C9H11HgNS2 Form Fine colourless
to grey-white powder. M.p.175C V.p. 1.1 101 mPa (35C) Solubility In water
6 mg/l (20C). In aniline 150, cyclohexanone 50, pyridine 50 (all in g/l); readily soluble
in chloroform; sparingly soluble in acetic acid, alcohols, diethyl ether, tetrahydrofuran.
Stability Stable at 180C and in water at pH 12.
COMMERCIALISATION:
History Fungicide introduced by Berk Chemicals (later Steetley Chemicals Ltd).
APPLICATIONS:
ModeofactionFungicide with low volatility and high stability. Uses Used to eradicate
Venturia spp. on most varieties of apples and pears at 1.53.0 g (as mercury)/100 l.
Phytotoxicity A few varieties of apple and pear are damaged by mercury compounds.
PRODUCTS:
Discontinued products Phelam* (Steetley).
ANALYSIS:
Mercury impurities determined (CIPACHandbook, 1994, F, 264).
JMPR Evaln. 9 (1967) EU Status (1107/2009) Aryl mercury compounds considered to be
outside the scope of the Directive; already banned, 79/117/EEC.
426
phenylmercury dimethyldithiocarbamate
Toxicity Class WHO (a.i.) O ECClassification Not specified, but organic mercury
generally is assigned T+; R26/27/28| R33| N; R50, R53 (concentration-dependent) PIC Yes.
phenylmercury nitrate
NOMENCLATURE:
Common name phenylmercury nitrate (BSI, E-ISO, chemical name, used in lieu of
common name, although the material used commercially is the basic nitrate with formula
as given); nitrate de ph(nylmercure) (draft F-ISO)
IUPACname phenylmercury hydroxide with phenylmercury nitrate; phenylmercury
nitrate (basic)
Chemical Abstracts name hydroxy(nitrato)diphenyldimercury CASRN[8003052]
SmilescodeO[Hg]c1ccccc1.[O-][N+](=O)O[Hg]c1ccccc1
PHYSICAL CHEMISTRY:
Composition See notes under Common name. Tech. has a mercury content of 63.4%
m/m. Mol. wt. 634.4 M.f. C12H11Hg2NO4 Form Colourless powder. M.p.c. 188C
(decomp.) Solubility In water 600 mg/kg (20C). In acetone 5, benzene 3, ethanol 1,
methanol 9 (g/kg, 20C).
COMMERCIALISATION:
History Fungicide introduced by Steetley Ltd.
APPLICATIONS: Uses Used against Venturia spp. on apples and pears,at 1.53.0 g (as
mercury)/100 l. Seed dressings, usually combined with an insecticide or another fungicide,
are used for cereals, sugar beet, fodder beet and mangolds. Phytotoxicity A few varieties
of apple and pear are damaged by mercury compounds.
PRODUCTS:
Discontinuedmixtures Harvesan Plus* (+gamma-HCH) (Steetley); Murcicide*
(+captan) (Steetley).
ANALYSIS:
973.11). Mercury impurities determined (CIPACHandbook, 1994, F, 264).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds.
EU Status (1107/2009) Aryl mercury compounds considered to be outside the scope of
the Directive; already banned, 79/117/EEC.
Other I.v. LD50 for rats 27 mg/kg. Toxicity Class WHO (a.i.) Ib ECClassification T;
R25, R48/24/25| C; R34| Xi; R37| R44 PIC Yes.
phenylmercury nitrate 427

phosacetim
Rodenticide
IRAC1B
NOMENCLATURE:
Common name phosac(time) ((f) F-ISO); phosacetim (BSI, E-ISO)
IUPACname O,O-bis(4-chlorophenyl) N-acetimidoylphosphoramidothioate
Chemical Abstracts name O,O-bis(4-chlorophenyl) (1-iminoethyl)phosphoramidothioate
CASRN[4104147] ECno2238747 DevelopmentcodesBayer 38 819
SmilescodeCC(=N)NP(=S)(Oc1ccc(Cl)cc1)Oc2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 375.2 M.f. C14H13Cl2N2O2PS
COMMERCIALISATION:
History Rodenticide reported by V. B. Richens (Pest Control, 1967, 35(9), 28). Introduced
by Bayer AG.
APPLICATIONS:
PRODUCTS:
Discontinued products Gophacide* (Bayer).
Toxicity Class WHO (a.i.) O ECClassification T+; R27/28| N; R50, R53
phosdiphen
Fungicide
Cl
O
Cl O P O Cl
OCH2CH3
Cl
NOMENCLATURE:
Common name phosdiphen (JMAF)
IUPACname bis(2,4-dichlorophenyl) ethyl phosphate
Chemical Abstracts name bis(2,4-dichlorophenyl) ethyl phosphate CASRN[36519
003] DevelopmentcodesMTO-460 (Mitsui Toatsu) SmilescodeCCOP(=O)
(Oc1ccc(Cl)cc1Cl)Oc2ccc(Cl)cc2Cl
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 416.0 M.f. C14H11Cl4O4P Form Pale yellow liquid
428 phosdiphen
(tech.). B.p. 175C /0.2 mmHg (tech.) V.p. 66 mPa (20C) (tech.) Henry 3.92 101 Pa
m3 mol1 (calc.) S.g./density 1.405 (25C, tech.) Solubility In water 0.7 mg/l (20C).
Soluble in acetone, xylene and hexane. Stability Stable in acidic media, but unstable in
alkaline media. Hydrolysis DT50 (25C) 7 d (pH 7), 4 d (pH 9). Thermally stable up to
200C.
COMMERCIALISATION:
History Fungicide reported by M. Hamada etal. (Ann. Phytopathol. Soc. Japan, 1971, 37,
365). Introduced by Hokko Chemical Industry Co., Ltd and Mitsui Toatsu Chemicals Inc.
(later Mitsui Chemicals Inc.). Patents JP 634549 (to Hokko) Manufacturers Hokko;
Mitsui Toatsu
APPLICATIONS: Uses Control of rice blast (Pyricularia oryzae).
ANALYSIS:
Oral Acute oral LD50 for male rats 6200, mice 5300 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >5000, mice 90009600 mg/kg.
APPLICATIONS:
(24 h) of tech. to skin and eyes of rabbits produced no irritation. NOEL (90 d) for
rats and mice 200 mg/kg diet; (2 y) for rats and mice 30 mg/kg diet. No reproductive,
teratogenic or mutagenic effects observed in rats. Toxicity Class WHO (a.i.) U EPA
(formulation) III
ECOTOXICOLOGY:
phosfolan
IRAC1B
NOMENCLATURE:
Common name phospholan ((m) F-ISO); phosfolan (BSI, E-ISO)
IUPACname diethyl 1,3-dithiolan-2-ylidenephosphoramidate;
2-(diethoxyphosphinylimino)-1,3-dithiolane
Chemical Abstracts name diethyl 1,3-dithiolan-2-ylidenephosphoramidate
CASRN[947024] ECno2134232 DevelopmentcodesEI 47 031 (Cyanamid)
SmilescodeCCOP(=O)(OCC)N=C1SCCS1
PHYSICAL CHEMISTRY: Mol. wt. 255.3 M.f. C7H14NO3PS2 Form Pale yellow solid.
M.p.36.5C; (tech., 3745C) B.p. 115118C /0.001 mmHg V.p. 0.031 mPa (20C)
Solubility In water 650 g/l. Soluble in acetone, benzene, cyclohexane, ethanol, and toluene.
phosfolan 429
Slightly soluble in diethyl ether. Sparingly soluble in hexane. Stability Stable under neutral
and slightly acidic conditions but hydrolysed at 2>pH>9.
COMMERCIALISATION:
History Insecticide introduced by American Cyanamid Co. Patents GB 974138; FR
1327386
APPLICATIONS:
Biochemistry Cholinesterase inhibitor ModeofactionSystemic insecticide and
acaricide with contact and stomach action. Uses Control of lepidopterous larvae
(particularly Spodoptera spp.), sucking insects, and mites on cotton, cabbage, onions,
tobacco, and other crops. Formulation types EC; GR .
PRODUCTS:
Discontinued products Cyalane* (Cyanamid); Cylan* (Cyanamid); Cyolan*
(Cyanamid); Cyolane* (Cyanamid).
ANALYSIS:
Residues determined by glc (N. R. Pasarela & E. J. Orloski, Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 231).
EHC 63 (1986), a general review of organophosphorus insecticides.
Oral Acute oral LD50 for male rats 8.9, male mice 12.1 mg/kg. Skin and eye Acute
percutaneous LD50 for male rabbits 23, male guinea pigs 54 mg/kg. NOEL In 90 d feeding
trials dogs receiving 1 mg/kg daily showed no clinical symptom. Toxicity Class WHO (a.i.)
Ia ECClassification T+; R27/28
ENVIRONMENTAL FATE:
Plants In plants, phosfolan is metabolised at the nitrogen-phosphorus bond to less toxic,
water-soluble compounds.
phosnichlor
Insecticide
IRAC1B
NOMENCLATURE:
Common name nichlorfos ((m) France); phosnichlor (BSI, E-ISO, (m) F-ISO)
CASRN[5826766] SmilescodeCOP(=S)(OC)Oc1ccc(Cl)c(c1)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 297.7 M.f. C8H9ClNO5PS
430 phosnichlor
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Isochlorthion* (Chemagro).
phoxim-methyl
Insecticide
IRAC1B
NOMENCLATURE:
Common name phoxime-m(thyl) ((f) F-ISO); phoxim-methyl (BSI, E-ISO)
IUPACname O,O-dimethyl -cyanobenzylideneamino-oxyphosphonothioate; dimethoxyp
hosphinothioyloxyimino(phenyl)acetonitrile
Chemical Abstracts name 3-methoxy-6-phenyl-2,4-dioxa-5-aza-3-phosphapept-5-
ene-7-nitrile 3-sulfide; -[[(dimethoxyphosphinothioyl)oxy]imino]benzeneacetonitrile
CASRN[14816161] DevelopmentcodesSRA 7760
SmilescodeCOP(=S)(OC)ON=C(C#N)c1ccccc1
COMMERCIALISATION:
History Superseded dimethyl analogue of phoxim (q.v.). Insecticide evaluated by Bayer AG.
APPLICATIONS:
pindone
Rodenticide
O
COC(CH3)3
O
NOMENCLATURE:
Common name no name (Portugal); pival* (former exception, Turkey); pivaldione
(France); pindone (BSI, E-ISO, (f) F-ISO)
IUPACname 2-pivaloylindan-1,3-dione
pindone 431
Chemical Abstracts name 2-(2,2-dimethyl-1-oxopropyl)-1H-indene-1,3(2H)-dione

CASRN[83261] ECno2014628
SmilescodeCC(C)(C)C(=O)C1C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
Mol. wt. 230.3 M.f. C14H14O3 Form Yellow crystals. M.p.108.5110.5C V.p. Very low
Solubility In water 18 mg/l (25C). Soluble in most organic solvents. Readily soluble in
aqueous alkalis or ammonia to give bright yellow salts. Stability Very stable.
COMMERCIALISATION:
History Insecticidal properties reported by L. B. Kilgore etal. (Ind. Eng. Chem., 1942, 34,
494). Introduced by Kilgore Chemical Co. Patents US 2310949
APPLICATIONS:
Biochemistry Anticoagulant; inhibits blood coagulation by blocking prothrombin
formation. Uses Control of rats and mice, in baits containing 250 mg/kg. Bait shyness
does not occur after feeding. Renders cereal bait resistant to insect infestation and fungal
infection. Formulation types AB; CB; CP; RB . Compatibility Compatible with other
rodenticides.
PRODUCTS:
Discontinued products Pival* (Marman, Motomco); Pivalyn* (sodium salt) (Motomco).
ANALYSIS:
ANALYSIS: by colorimetry (J. B. La Clair, J. Assoc. Off. Agric. Chem., 1955, 38, 299).
EHC 175 (1995). ICSC.515 (2004).
Oral Acute oral LD50 for rats 280, rabbits 150170, dogs 75100 mg/kg. Chronic oral LD50
for rabbits 0.52, dogs 2.5, sheep >12 mg/kg daily. Other Acute LD50 by injection for rats
isc.50 mg/kg, but it is more toxic when given in small daily doses of 1535 mg/kg. Dogs are
killed by daily doses of 2.5 mg/kg (J. R. Beauregard et al., J. Agric. Food Chem., 1955, 3, 124;
J. P. Saunders et al., ibid., p. 762). Toxicity Class WHO (a.i.) Ib ECClassification T; R25,
R48/25| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks 250, bobwhite quail 1560 mg/kg. Fish LC50 (96
h) for bluegill sunfish 1.6, rainbow trout 0.21 mg/l.
piproctanyl bromide
NOMENCLATURE:
Common name piproctanyl (for cation) (BSI, E-ISO, (m) F-ISO)
IUPACname 1-allyl-1-(3,7-dimethyloctyl)piperidinium bromide
432 piproctanyl bromide

Chemical Abstracts name 1-(3,7-dimethyloctyl)-1-(2-propenyl)piperidinium

bromide CASRN[56717114] piproctanyl bromide; [69309473] piproctanyl
DevelopmentcodesRo 060761/000 (Dr Maag); ACR-1222
Smilescode[Br-].CC(C)CCCC(C)CC[N+]1(CC=C)CCCCC1
PHYSICAL CHEMISTRY: Mol. wt. 346.4; (piproctanyl 266.5) M.f. piproctanyl bromide
C18H36BrN; piproctanyl C18H36N Form Pale yellow wax. M.p.75C
V.p. <5 105 mPa (20C) Solubility Very soluble in water. In methanol >2400, ethanol
2100, acetone 1400 (all in g/l). Practically insoluble in hexane and cyclohexane. Stability In
aqueous solutions, stable for up to 3 years under normal conditions. Stable to hydrolysis at
50C (pH 3 to pH 13). Stable to light, and up to 100C.
COMMERCIALISATION:
History Plant growth regulator reported by G. A. Hppi etal. (Experientia, 1976, 32,
37). The bromide introduced by Dr R. Maag Ltd. Patents DE 2459129 (to Hoffmann-La
Roche)
APPLICATIONS:
ModeofactionPlant growth regulator, absorbed by the leaves and roots, but not readily
translocated between shoots. Inhibits elongation of internodes, and shortens and stiffens
stems and peduncles. Uses Inhibition of longitudinal growth (to produce more compact
and sturdier plants) in ornamentals, especially chrysanthemums, but also azaleas, fuchsias,
petunias, and calceolarias. Formulation types SL .
PRODUCTS:
Discontinued products Alden* (Dr Maag); Stemtrol* (Dr Maag).
ANALYSIS:
Product analysis by reaction with sodium phenylsulfide to form allyl phenyl sulfide which is
determined by glc. Residues determined in the same way.
percutaneous LD50 for rats 115240 mg/kg. Non-irritating to skin (guinea pigs) and eyes
(rabbits). Inhalation LC50 for rats 1.5 mg/l air. NOEL In 90 d feeding trials, rats receiving
150 mg/kg daily and dogs receiving 25 mg/kg daily showed no significant ill-effects.
ECOTOXICOLOGY:
Fish LC50 (96 h) for rainbow trout 12.7, bluegill sunfish 62 mg/l. Bees Not toxic to bees.
piproctanyl bromide 433

piprotal
NOMENCLATURE:
Common name piprotal (ESA)
IUPACname 5-[bis[2-(2-butoxyethoxy)ethoxy]methyl]-1,3-benzodioxole (I); 1-bis[2-(2-
butoxyethoxy)ethoxy]methyl-3,4-methylenedioxybenzene
SmilescodeCCCCOCCOCCOC(OCCOCCOCCCC)c1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
Mol. wt. 456.6 M.f. C24H40O8
COMMERCIALISATION:
History Synergist for pyrethrum reported by L. O. Hopkins & D. R. Maciver (Pyrethrum
Post, 1965, 8(2), 3). Introduced by McLaughlin Gormley King Co.
PRODUCTS:
Discontinued products Tropital* (MGK).
pirimetaphos
Insecticide
IRAC1B
NOMENCLATURE:
Common name pirimetaphos (BSI, E-ISO, (m) F-ISO); pyrim(taphos) (France)
IUPACname 2-diethylamino-6-methylpyrimidin-4-yl methyl methylphosphoramidate
Chemical Abstracts name 2-(diethylamino)-6-methyl-4-pyrimidinyl methyl
methylphosphoramidate CASRN[31377692] DevelopmentcodesSAN I 52 135
SmilescodeCCN(CC)c1nc(C)cc(OP(=O)(NC)OC)n1
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG.
APPLICATIONS:
434 pirimetaphos
pirimiphos-ethyl
Insecticide
CH3 S
P(OCH2CH3)2
N O
N
(CH3CH2)2N
IRAC1B
NOMENCLATURE:
Common name pirimiphos-ethyl (BSI, E-ISO, ANSI, BAN, ESA); pyrimiphos-(thyl) ((m)
F-ISO)
IUPACname O,O-diethyl O-2-diethylamino-6-methylpyrimidin-4-yl phosphorothioate
Chemical Abstracts name O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]
O,O-diethyl phosphorothioate CASRN[23505411] ECno2457040
DevelopmentcodesPP211 SmilescodeCCOP(=S)(OCC)Oc1cc(C)nc(n1)N(CC)CC
PHYSICAL CHEMISTRY:
Composition Tech. is 95% pure. Mol. wt. 333.4 M.f. C13H24N3O3PS Form Straw-
coloured liquid; (tech. is a clear red-brown liquid with a mercaptan-like odour).
M.p.1518C (tech.) B.p. Decomposes abovec.194C V.p. 0.68 mPa (20C); 39 mPa
(25C) Kow logP = 5.0 (unionised) S.g./density 1.14 (20C) Solubility In water 2.3 mg/l
(pH 7.2). Miscible with most organic solvents. Stability Stable for at least 1 year at room
temperature, and for at least 5 days at 80C. Hydrolysed by acid and base; DT50 (25C)
521200 d (pH range 5.58.5), most stable pH 78. F.p. >60C
COMMERCIALISATION:
History Superseded diethyl homologue of pirimiphos-methyl (q.v.). Insecticide introduced
by ICI Plant Protection Division (later Zeneca Agrochemicals). Patents GB 1019227; GB
1205000 Manufacturers Hunan Haili
APPLICATIONS:
respiratory action. Uses Broad-spectrum control of Diptera and Coleoptera soil pests
and some foliar pests on bananas and other fruit, field crops, ornamentals, turf, vegetables,
etc. Also used as a seed treatment, and in compost to control sciarid and phorid flies on
mushrooms. Phytotoxicity Phytotoxic at high rates of seed dressing.
Formulation types DS; EC; GR; CG.
PRODUCTS:
Discontinued products Fernex* (Zeneca); Primicid* (Zeneca); Solgard* (Zeneca).
ANALYSIS:
Product analysis by glc with FID (CIPACHandbook, 1988, D, 146). Identity also by glc, tlc, i.r.
pirimiphos-ethyl 435
or nmr (CIPACHandbook, 1994, F, 406). Residues determined by glc with FPD or FTD (D. J.
W. Bullock, Anal. Methods Pestic. Plant Growth Regul., 1976, 8, 171).
Oral Acute oral LD50 for rats 140200, guinea pigs 50100, cats 2550 mg/kg.
Skin and eye Acute percutaneous LD50 for male rats 10002000 mg/kg. Non-irritating to
skin; may cause eye irritation (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation LC50 (6 h) for rats >5 ppm (no toxic effects over 3 w). NOEL (90 d) for rats
1.6 mg/kg diet (0.08 mg/kg daily); for dogs 0.2 mg/kg daily. For rats receiving 27 mg/kg diet
(1.6 mg/kg daily) and dogs 2 mg/kg daily, the only effect was on the cholinesterase levels.
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassification T; R25| Xn; R21| N;
R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 2.5, bobwhite quail 1020 mg/kg. Fish LC50 (96 h)
for common carp 0.22, brown trout 0.02 mg/l. Daphnia LC50 (48 h) 0.3 g/l. Bees Toxic
to bees.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 2170 d (non-sterile, aerobic, o.m. 1.86.3%, pH 6.07.5).
For details of persistence in soil, see D. L. Suett, Pestic. Sci., 1975, 6, 385.
polychlorodicyclopentadiene isomers
NOMENCLATURE:
IUPACname polychlorodicyclopentadiene isomers
CASRN[8029296]
COMMERCIALISATION:
History Insecticide and herbicide introduced by Velsicol Chemical Corp.
PRODUCTS:
Discontinued products Bandane* (Velsicol).
polychloroterpenes
NOMENCLATURE:
IUPACname heptachloro-2,2-dimethyl-3-methylene-8,9,10-trinorbornane
436 polychloroterpenes
Chemical Abstracts name chlorinated mixed terpenes Other names terpene

polychlorinates CASRN[8001501] DevelopmentcodesCompound 3961
PHYSICAL CHEMISTRY:
Mol. wt. 379.4 M.f. C10H11Cl7 (65% Cl)
COMMERCIALISATION:
History Insecticidal and acaricidal activity of this reaction mixture described by D. L. Kent
etal. (Soap Chem. Spec., 1953, 19(6), 157). Introduced by Goodrich Chemical Co.
PRODUCTS:
Discontinued products Strobane* (Goodrich).
ANALYSIS:
Product analysis by tlc (AOACMethods 18th Ed., 972.05).
IARC Monographs Programme on the Evaluation of Carcinogenic Risks (1974) 5. IARC 5
(1974).
IARC Class 3
polynactins
Acaricide
R1 O
CH3
CH3
O O
O
O O
R4
O O R2
O
O O
CH3 R3 CH3
O

dinactin: R1, R3 = CH3- ; R2, R4 = CH3CH2-
NOMENCLATURE:
trinactin: R1 = CH3- ; R2, R3, R4 = CH3CH2-
IUPACname [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28
tetranactin: R1, R2, R3, R4 = CH3CH2-
S*,29S*,32S*,34S*)]-5,14,23,32-tetraethyl-2,11,20,29-tetramethyl-4,13,22,31,37,38,3-
9,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(tetranactin); [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S
*,29S*,32S*,34S*)]-5,14,23-triethyl-2,11,20,29,32-pentamethyl-4,13,22,31,37,38,39,-
40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(trinactin); [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,
polynactins 437
29S*,32S*,34S*)]-5,23-diethyl-2,11,14,20,29,32-hexamethyl-4,13,22,31,37,38,39,40-
-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone (dinactin)
Chemical Abstracts name [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,2
5R*,28S*,29S*,32S*,34S*)]-5,14,23,32-tetraethyl-2,11,20,29-tetramethyl-4,13,22,31,37,38,3-
9,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(tetranactin) Other names tetranactin; trinactin; dinactin CASRN[33956615]
tetranactin; [7561719] trinactin; [20261852] dinactin; [39285046] polynactin,
formerly [56485451] and [56573638] Smilescodetetranactin, without
stereochemistry:CCC1CC2CCC(O2)C(C)C(=O)OC(CC)CC3CCC(O3)C(C)C(=O)
OC(CC)CC4CCC(O4)C(C)C(=O)OC(CC)CC5CCC(O5)C(C)C(=O)O1
PHYSICAL CHEMISTRY:
Composition A mixture of tetranactin, trinactin and dinactin. Mol. wt. 793.1
(tetranactin); 779.0 (trinactin); 765.0 (dinactin) M.f. C44H72O12 (tetranactin); C43H70O12
(trinactin); C42H68O12 (dinactin) M.p.111112C Solubility In water 0.02 g/l (25C).
In acetone 56, methanol 17, benzene 387, xylene 243, hexane 8 (all in g/l, 25C).
COMMERCIALISATION:
Production By fermentation of Streptomyces aureus S-3466.
APPLICATIONS:
Biochemistry Thought to act through leakage of cations through the lipid layer of the
mitochondrial membrane. Uses For control of spider mites in fruit trees.
PRODUCTS:
Discontinuedmixtures Mitecidin* (+fenobucarb) (Eiko Kasei); Mitedown*
(+fenbutatin oxide) (Eiko Kasei).
Oral Acute oral LD50 for mice >15000 mg/kg. Skin and eye Acute percutaneous LD50 for
mice >10000 mg/kg. Mild skin and eye irritant. Toxicity Class EPA (formulation) IV
ECOTOXICOLOGY:
Fish TLm for carp 0.003 ppm.
potassium cyanate
Herbicide
NOMENCLATURE:
IUPACname potassium cyanate (I)
Smilescode[K+].[O-]C#N
PHYSICAL CHEMISTRY:
Mol. wt. 81.12 M.f. CKNO Form Colourless crystals. S.g./density 2.056 (20C)
Solubility In water 630 g/l (10C), 720 g/l (70C).
438 potassium cyanate

Stability Slowly hydrolysed in aqueous solution to form ammonia and potassium

bicarbonate.
COMMERCIALISATION:
History Introduced as herbicide by American Cyanamid Co.
APPLICATIONS:
ModeofactionTotal herbicide. Formulation types SP.
PRODUCTS:
Discontinued products Aerocyanate* (Cyanamid).
ANALYSIS:
Product analysis by conversion to an insoluble derivative which is weighed
(CIPACHandbook, 1985, 1C, 2200; AOACMethods, 18th Ed., 952.01).
potassium phosphates
Fungicide
NOMENCLATURE:
Chemical Abstracts name monopotassium phosphate
Other names potassium dihydrogen phosphate; potassium monophosphate; dipotassium
phosphate; dipotassium hydrogen phosphate CASRN[7778770] monopotassium salt;
[7758114] dipotassium salt
PHYSICAL CHEMISTRY:
Mol. wt. 136.1 (monopotassium salt); 174.2 (dipotassium salt) M.f. H2KO4P; HK2O4P
Form Crystalline powder. M.p.>465C (dipotassium salt) Solubility In water 150 g/100
g. (dipotassium salt)
COMMERCIALISATION:
History The dipotassium salt was first registered in USA in 2002.
Manufacturers Lidochem
APPLICATIONS:
ModeofactionThe dipotassium salt may act both by direct toxicity to the pathogen and
also, through its fertiliser action, by stimulating the plants natural defences.
Uses The monopotassium salt is for control of powdery mildew in fruit and vegetables.
Also used as a fertiliser, and as a buffering agent in pesticide formulations. The dipotassium
salt is for control of powdery mildews, Downy mildews, leaf spot, root rot, etc in woody
ornamentals, turf, grapes, and fruit and nut trees which are not yet bearing.
PRODUCTS:
Other products Nutrol (dihydrogen phosphate) (Lidochem);
Discontinued products eKsPunge* (dihydrogen phosphate) (Lidochem).
potassium phosphates 439


ICSC.608 (potassium dihydrogen phosphate; 2005).
Oral Acute oral LD50 for male rats >5000, female rats >500 mg/kg (dihydrogen phosphate).
Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not a skin irritant; a mild
eye irritant (dihydrogen phosphate).
primidophos
Insecticide
IRAC1B
NOMENCLATURE:
Common name prymidophos ((m) France); primidophos (BSI, E-ISO, (m) F-ISO)
IUPACname O,O-diethyl O-(2-N-ethylacetamido-6-methylpyrimidin-4-yl)
phosphorothioate; N-(4-diethoxyphosphinothioyloxy-6-methylpyrimidin-2-yl)-N-
ethylacetamide
Chemical Abstracts name O-[2-(acetylethylamino)-6-methyl-4-pyrimidinyl] O,O-
diethyl phosphorothioate CASRN[39247966] DevelopmentcodesPP484
SmilescodeCCOP(=S)(OCC)Oc1cc(C)nc(n1)N(CC)C(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 347.4 M.f. C13H22N3O4PS
COMMERCIALISATION:
History Insecticide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
APPLICATIONS:
proclonol
Acaricide
NOMENCLATURE:
Common name proclonol (BAN, JMAF)
IUPACname 4,4-dichloro--cyclopropylbenzhydrol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--cyclopropylbenzenemethanol
CASRN[14088712] DevelopmentcodesR-8284 (Janssen)
SmilescodeOC(C1CC1)(c2ccc(Cl)cc2)c3ccc(Cl)cc3
PHYSICAL CHEMISTRY:
Mol. wt. 293.2 M.f. C16H14Cl2O
440 proclonol
COMMERCIALISATION:
History Acaricide introduced by Janssen Pharmaceutica, N.V.
PRODUCTS:
Discontinued products Kilacar* (Asepta).
procyazine
Herbicide
NOMENCLATURE:
Common name procyazine (BSI, E-ISO, (f) F-ISO, ANSI)
IUPACname 2-(4-chloro-6-cyclopropylamino-1,3,5-triazin-2-ylamino)-2-
methylpropiononitrile
Chemical Abstracts name 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-triazin-2-yl]amino]-
2-methylpropanenitrile CASRN[32889488] DevelopmentcodesCGA 18 762
SmilescodeCC(C)(Nc1nc(Cl)nc(NC2CC2)n1)C#N
PHYSICAL CHEMISTRY:
Mol. wt. 252.7 M.f. C10H13ClN6
COMMERCIALISATION:
History Herbicide introduced by Ciba-Geigy AG.
ANALYSIS:
See Pestic. Anal. Man., I, 302.
profluazol
Herbicide
HRACE WSSA 14
NOMENCLATURE:
Common name profluazol (BSI, E-ISO, (m) F-ISO)
IUPACname 1,2-dichloro-4-fluoro-5-[(6S,7aR)-6-fluoro-2,3,5,6,7,7a-hexahydro-1,3-
dioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]methanesulfonanilide
Chemical Abstracts name 1-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-
6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]phenyl]
methanesulfonamide CASRN[190314433] DevelopmentcodesIN-TY029; DPX-
TY029 (DuPont)
PHYSICAL CHEMISTRY:
Mol. wt. 414.2 M.f. C13H11Cl2F2N3O4S
COMMERCIALISATION:
History Herbicide developed by E. I. du Pont de Nemours & Co.
profluazol 441
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase.
profluralin
Herbicide
NO2
CH2
F3C N
CH2CH2CH3
NO2
NOMENCLATURE:
Common name profluralin (BSI, E-ISO, ANSI, WSSA); profluraline ((f) F-ISO)
IUPACname N-(cyclopropylmethyl)-,,-trifluoro-2,6-dinitro-N-propyl-p-toluidine;
N-cyclopropylmethyl-2,6-dinitro-N-propyl-4-trifluoromethylaniline
Chemical Abstracts name N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4-
(trifluoromethyl)benzenamine CASRN[26399360] ECno2476566
DevelopmentcodesCGA 10 832
SmilescodeCCCN(CC1CC1)c2c(cc(cc2[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 347.3 M.f. C14H16F3N3O4 Form Yellow-orange crystals. M.p.32.132.5C
V.p. 8.4 mPa (20C) Henry 2.92 101 Pa m3 mol1 (calc.) S.g./density 1.38 (20C)
Solubility In water 0.1 mg/l (20C). In n-octanol 220 g/l (20C); readily soluble in most
organic solvents, e.g. ethanol, acetone, xylene, and n-hexane. Stability Stable for at least
3 years under normal storage conditions. Solutions are slowly hydrolysed at 100C; DT50
6 h (pH 3, pH 7 and pH 10). Decomposed by uv light. Decomposes atc.180C.
COMMERCIALISATION:
History Herbicide reported by T. D. Taylor etal. (Annu. Meet. Weed Sci. Soc. Am., 1973,
Abstr. 169). Introduced by Ciba-Geigy AG. Patents US 3546295
APPLICATIONS:
ModeofactionSelective herbicide, absorbed by the roots and shoots. Uses Control
of annual and perennial broad-leaved and grass weeds in cotton, soya beans, brassicas,
capsicums, tomatoes, and other crops. Applied pre-planting by soil incorporation at
0.751.5 kg/ha. Phytotoxicity Small grains, sorghum, maize, beet and direct-seeded
tomatoes are sensitive. Formulation types EC.
PRODUCTS:
Discontinued products Pregard* (Ciba-Geigy); Tolban* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with FID (R. A. Kahrs, Anal. Methods Pestic. Plant Growth Regul., 1978,
10, 451). Residues determined by glc with ECD or MCD (idem, ibid.).
442 profluralin
Oral Acute oral LD50 for ratsc.10000 mg/kg. Skin and eye Acute percutaneous LD50 for
rabbits >4000, rats >3170 mg/kg. Non-irritating to skin; moderate eye irritant (rabbits).
Inhalation LC50 (4 h) for rats >3.97 mg/l air. NOEL (90 d) for rats 200 mg/kg diet (c.
13 mg/kg daily); for dogs 600 mg/kg diet (c. 20 mg/kg daily). Toxicity Class WHO (a.i.) U
ECClassification Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail and mallard ducks 1000 mg/kg. Fish LC50 (96 h)
for bluegill sunfish 0.023, trout 0.015 mg/l. Bees Toxic to honeybees.
ENVIRONMENTAL FATE:
Animals For details of metabolites see A. R. Jacobson and J. T. Gerig (Chem Res. Toxicol.
1988, 1, 304). Plants Minute quantities of polar metabolites are produced in cotton and
soya beans. Soil/Environment Degraded by soil micro-organisms. No significant leaching
through the soil.
proglinazine-ethyl; proglinazine
Herbicide
Cl N NHCH2CO2H
N N
(CH3)2CHNH
NOMENCLATURE:
Common name proglinazine (for the acid) (BSI, E-ISO, (f) F-ISO, WSSA)
IUPACname N-(4-chloro-6-isopropylamino-1,3,5-triazin-2-yl)glycine (for the acid)
Chemical Abstracts name N-[4-chloro-6-[(1-methylethyl)amino]-1,3,5-triazin-
2-yl]glycine (for the acid) CASRN[68228182] ester; [68228206] acid
DevelopmentcodesMG-07 (acid) (Nitrokmia)
PHYSICAL CHEMISTRY:
Composition Tech. isc.94%. Mol. wt. 273.3 (ester); 245.7 (acid) M.f. ester C10H16ClN5O2;
acid C8H12ClN5O2 Form Colourless crystals (ester). M.p.110112C (ester)
V.p. 0.27 mPa (20C) (ester) Solubility In water 750 mg/l (25C, ester). In acetone 500,
hexane 35, xylene 100 (all in g/l, 25C, ester). Stability Decomposes at 160C; stable to
light. Stable at room temperature (pH 58), but on heating is hydrolysed by acid or alkali to
the corresponding herbicidally-inactive hydroxytriazine.
COMMERCIALISATION:
History The ethyl ester introduced as a herbicide by Nitrokmia Ipartelepek.
proglinazine-ethyl; proglinazine 443

APPLICATIONS:
site. ModeofactionSelective herbicide. Uses Pre-emergence control of seedling weeds
(particularly broad-leaved) in maize at 4 kg/ha. Formulation types WP
ANALYSIS:
Oral Acute oral LD50 for rats and mice >8000, rabbits >3000, guinea pigs 857923 mg/
kg. Skin and eye Acute percutaneous LD50 for rabbits >4000, rats >1500 mg/kg. Non-
irritating to skin and eyes (rabbits). Moderate skin sensitisation (guinea pigs). Other Acute
i.p. LD50 for rats 829891, mice 7201080 mg/kg. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soil, DT50 5670 d.
promacyl
CH3
OCONCOCH2CH2CH3
CH3 CH(CH3)2
IRAC1A
NOMENCLATURE:
Common name promacyl (Australia)
IUPACname 5-methyl-m-cumenyl butyryl(methyl)carbamate
Chemical Abstracts name 3-methyl-5-(1-methylethyl)phenyl methyl(1-
oxobutyl)carbamate Other names promecarb A CASRN[34264249]
DevelopmentcodesCRC 7320
SmilescodeCCCC(=O)N(C)C(=O)Oc1cc(C)cc(c1)C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 277.4 M.f. C16H23NO3 Form Tech. is a clear amber to dark brown liquid.
B.p. 158C /5 mmHg V.p. 400 Pa (149C) S.g./density 0.996 (20C)
Solubility Sparingly soluble in water. Miscible with aliphatic and aromatic hydrocarbons,
alcohols, esters, ethers, ketones. Stability Stable 200C; also unchanged after 300 d at
50C.
COMMERCIALISATION:
History Insecticide and ixodicide introduced by ICI Australia (later Crop Care Australasia
Pty Ltd). Patents AU 441004; AU 454280
444 promacyl
APPLICATIONS:
Biochemistry Cholinesterase inhibitor Uses Effective for controlling Boophilus
microplus on cattle by sprays or plunge dips. Also controls Haemaphysalis longicornis,
Haematobia irritans exigua and Ixodes holocyclus on cattle and horses.
PRODUCTS:
Discontinued products Promicide* (ICI Australia).
ANALYSIS:
Product analysis by glc (D. Gunew, Anal. Methods Pestic. Plant Growth Regul., 1980, 11, 139).
Residues in cattle determined by glc (D. E. Clegg & P. R. Martin, Pestic. Sci., 1973, 4, 447).
Oral Acute oral LD50 for female rats 1220, female mice 20004000, female guinea pigs 250,
female rabbits 8000 mg/kg. Skin and eye Acute percutaneous LD50 for female rats >4000
mg/kg. Slight irritant to skin (rats). Inhalation No toxic sign in rats exposed to saturated
atmosphere for 6 h/d each 5 d/w for 3 w. NOEL (2 y) for rats 500 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens 40008000 mg/kg.
promecarb
Insecticide
OCONHCH3
CH3 CH(CH3)2
IRAC1A
NOMENCLATURE:
Common name promecarb (BSI, E-ISO, ESA, JMAF); prom(carbe) ((m) F-ISO)
IUPACname 5-methyl m-cumenyl methylcarbamate; 3-isopropyl-5-methylphenyl
methylcarbamate
Chemical Abstracts name 3-methyl-5-(1-methylethyl)phenyl methylcarbamate
CASRN[2631370] ECno2201130 DevelopmentcodesSN 34 615; SSI 0792
SmilescodeCNC(=O)Oc1cc(C)cc(c1)C(C)C
PHYSICAL CHEMISTRY:
Composition Tech. is >97%. Mol. wt. 207.3 M.f. C12H17NO2 Form Colourless crystals.
promecarb 445
M.p.8787.5C B.p. 117C /0.01 mmHg V.p. 1.4 mPa (25C) Kow logP = 3.189 (pH 4)
Henry 3.19 103 Pa m3 mol1 (calc.) Solubility In water 91 mg/l (pH 45, 25C). Readily
soluble in organic solvents, e.g. in acetone, DMF, dichloroethane 400600, cyclohexanol,
cyclohexanone, isopropanol, isobutanol, methanol 200400, carbon tetrachloride, xylene
100200 (all in g/l, 25C). Stability Hydrolysed by strong acids and alkalis, DT50 (22C)
103 d (pH 7), 36 h (pH 9), stable at pH 5. Stable 250C, and >140 h at 50C.
COMMERCIALISATION:
History Insecticide reported by A. Formigoni & G. P. Bellini (Congr. Int. Antiparassitari,
Naples, 1965) and by A. Jger (Z. Angew. Entomol., 1966, 58, 188). Introduced by Schering
AG (later AgrEvo GmbH). Patents DE 1156272
APPLICATIONS:
with contact and stomach action; has good initial knockdown of insects. Uses Control of
sucking and chewing insects (Colorado Beetles and other Coleoptera, aphids, Lepidoptera
larvae, leaf miners, etc.) in potatoes, maize, pome fruit, stone fruit, and citrus fruit.
Formulation types EC; WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Carbamult* (AgrEvo).
ANALYSIS:
Product analysis by hplc Residues determined by glc with ECD of a derivative.
percutaneous LD50 for rabbits >2025 mg/kg; (50% WP formulation) for rats and rabbits
>1000 mg/kg. Inhalation LC50 (4 h) for rats >0.16 mg/l air. NOEL (1.5 y) for rats >20 mg/
kg. Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassification T; R25| N; R50,
R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 78, mallard ducks 3.5 mg/kg. Fish LC50 (96 h) for
rainbow trout 0.3, bluegill sunfish 0.64 mg/l; (72 h) for carp 4.3 mg/l; (120 h) for European
trout 1.2 mg/l. Bees Toxic to bees; LD50 0.0011 mg/bee.
ENVIRONMENTAL FATE:
Animals In mammals, the substituted phenol moiety is eliminated after condensation
with glucuronic acid. Metabolism of carbamate insecticides is reviewed (M. Cool & C.
K. Jankowski in Insecticides). Soil/Environment Presumably, as for other carbamates,
cleavage of the N-methylcarbamate moiety and decomposition into CO2 and methylamine.
Soil DT50 <28 d (lab. and field studies). Soil adsorption Kd 1.72 (2.64% o.c., pH 6.0), 1.63
(1.01% o.c., pH 6.7).
446 promecarb
propaphos
Insecticide
O
P(OCH2CH2CH3)2
CH3S O
IRAC1B
NOMENCLATURE:
Common name propaphos (BSI, JMAF, E-ISO); propafos ((m) F-ISO)
IUPACname 4-(methylthio)phenyl dipropyl phosphate
Chemical Abstracts name 4-(methylthio)phenyl dipropyl phosphate
Other names DPMP CASRN[7292162] DevelopmentcodesNK-1158 (Nippon
Kayaku) SmilescodeCCCOP(=O)(OCCC)Oc1ccc(SC)cc1
PHYSICAL CHEMISTRY: Mol. wt. 304.3 M.f. C13H21O4PS Form Colourless liquid.
B.p. 175177C /0.85 mmHg V.p. 0.12 mPa (25C) Kow logP = 3.67
125 mg/l (25C). Soluble in most organic solvents. Stability Stable <230C; stable in
neutral and acidic media, but is slowly decomposed in alkaline media.
COMMERCIALISATION:
History Insecticide reported (Jpn. Pestic. Inf., 1970, No. 4, p. 7). Introduced by Nippon
Kayaku Co., Ltd and first marketed in Japan in 1973. Patents JP 482500; JP 462729
Manufacturers Nippon Kayaku
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic insecticide
with contact and stomach action. Uses Control of Chilo suppressalis, Laodelphax
striatella, Nephotettix cincticeps, Oulema oryzae (including strains resistant to other
organophosphorus and carbamate insecticides) in paddy rice. Applied at 35 g/rice nursery
tray. Formulation types DP; GR .
PRODUCTS:
Discontinued products Kayaphos* (Nippon Kayaku); Discontinuedmixtures Fuji-
One Kayaphos Oncol* (+benfuracarb +isoprothiolane) (Nihon Nohyaku).
ANALYSIS:
Product and residue analysis by glc (S. Asaka et al., Noyaku Kagayu, 1975, 3, 36).
EHC 63 (1986) is a general review of organophosphorus insecticides. J. Pestic. Sci., 1989, 14,
511515. EU Status (1107/2009) Never notified to the EU.
Oral Acute oral LD50 for rats 70, mice 90, rabbits 82.5 mg/kg. Skin and eye Acute
propaphos 447
percutaneous LD50 for rats 88.5 mg/kg. Inhalation LC50 for rats 39.2 mg/m3. NOEL (2 y)
for rats 0.08, mice 0.05 mg/kg b.w. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Birds LD50 for chickens 2.55.0 mg/kg. Fish LC50 (48 h) for carp 4.8 mg/l. Daphnia Toxic.
Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants For metabolism in plants, see Y. Fujii et al., J. Pestic. Sci., 1980, 5(1), 5562.
propyl 3-tert-butylphenoxyacetate
NOMENCLATURE:
IUPACname propyl 3-tert-butylphenoxyacetate
Chemical Abstracts name propyl [3-(1,1-dimethylethyl)phenoxy]acetate
CASRN[66227096] DevelopmentcodesM&B 25 105
SmilescodeCCCOC(=O)COc1cccc(c1)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C15H22O3 Form Colourless liquid with a characteristic odour. B.p.
162C /20 mmHg Solubility Sparingly soluble in water.
COMMERCIALISATION:
History Plant growth-regulating properties reported by C. J. Hibbitt & J. A. Hardisty
(Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1979, 44, 835). Introduced by May & Baker Ltd
(later Rhne-Poulenc Agrochimie). Patents GB 1524320
APPLICATIONS: Uses Promotes lateral branching in maiden and young non-cropping
apple and pear trees by temporarily inhibiting the growth of the apical meristem.
PRODUCTS:
Discontinued products M&B 25105* (Hortichem).
ANALYSIS:
>2000 mg/kg. Moderate irritant to skin and eyes (rabbits).
448
propyl 3-tert-butylphenoxyacetate
propyl isome
NOMENCLATURE:
Common name propyl isome (ESA)
IUPACname dipropyl 5,6,7,8-tetrahydro-7-methylnaphtho[2,3-d]-1,3-dioxole-5,6-
dicarboxylate (I); dipropyl 1,2,3,4-tetrahydro-3-methyl-6,7-methylenedioxynaphthalene-1,2-
dicarboxylate
Chemical Abstracts name (I) Other names dipropyl maleate isosafrole condensate
CASRN[83590] SmilescodeCCCOC(=O)C1C(C)Cc2cc3OCOc3cc2C1C(=O)
OCCC
COMMERCIALISATION:
History Synergist for pyrethrum reported by M. E. Synerholm & A. Hartzell (Contr. Boyce
Thompson Inst., 1945, 14, 79). Introduced by S. B. Penick & Co.
Toxicity Class WHO (a.i.) O ECClassification T; R24| Xn; R22| N; R50, R53
prosulfalin
Herbicide
NOMENCLATURE:
Common name prosulfaline ((m) F-ISO); prosulfalin (BSI, E-ISO, ANSI, WSSA)
IUPACname N-(4-dipropylamino-3,5-dinitrophenylsulfonyl)-S,S-dimethylsulfimide
Chemical Abstracts name N-[[4-(dipropylamino)-3,5-dinitrophenyl]sulfonyl]-S,S-
dimethylsulfilimine CASRN[51528031]
SmilescodeCCCN(CCC)c1c(cc(cc1[N+](=O)[O-])S(=O)(=O)N=S(C)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 406.5 M.f. C14H22N4O6S2
COMMERCIALISATION:
History Herbicide evaluated by Eli Lilly & Co.
prothidathion
Acaricide
IRAC1B
NOMENCLATURE:
Common name prothidathion (BSI, E-ISO, (m) F-ISO)
IUPACname S-2,3-dihydro-5-isopropoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-diethyl
prothidathion 449
phosphorodithioate; 3-diethoxyphosphinothioylthiomethyl-5-isopropoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name O,O-diethyl S-[[5-(1-methylethoxy)-2-oxo-1,3,4-thiadiazol-
3(2H)-yl]methyl] phosphorodithioate CASRN[20276839]
DevelopmentcodesGS 13 010
SmilescodeCCOP(=S)(OCC)SCn1nc(OC(C)C)sc1=O
COMMERCIALISATION:
History Acaricide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
prothiocarb; prothiocarb hydrochloride

Fungicide
FRAC28, F4; carbamate fungicide
NOMENCLATURE:
Common name prothiocarbe ((m) F-ISO); prothiocarb (BSI, E-ISO)
IUPACname S-ethyl (3-dimethylaminopropyl)thiocarbamate
Chemical Abstracts name S-ethyl [3-(dimethylamino)propyl]carbamothioate
CASRN[19622083] prothiocarb; [19622196] hydrochloride ECno2431939
hydrochloride DevelopmentcodesSN 41 703 (Schering)
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 190.3; (hydrochloride 226.8) M.f. C8H18N2OS;
(hydrochloride C8H19ClN2OS) Form Prothiocarb hydrochloride is a hygroscopic,
colourless, odourless crystalline solid; (tech. has a strong odour). M.p.120121C
(hydrochloride) V.p. 0.0019 mPa (25C, hydrochloride) Henry hydrochloride: 4 1010
Pa m3 mol1 (calc.) Solubility Hydrochloride: In water 890 g/l (23C). In benzene, hexane
<0.15, chloroform 100, methanol 680 (all in g/l, 23C).
COMMERCIALISATION:
History Fungicide reported by M. G. Bastiaansen etal. (Meded. Fac. Landbouwwet. Rijksuniv.
Gent, 1974, 39, 1019). The hydrochloride introduced by Schering AG. Patents DE 1567169.
APPLICATIONS:
Biochemistry Proposed mode of action is affecting cell membrane permeability, by
inhibiting fatty acid biosynthesis. ModeofactionSystemic fungicide, taken up by the
roots and translocated to the aerial parts. Uses Prothiocarb hydrochloride is a soil-applied
fungicide with a specific action against Phycomycetes, e.g. Phytophthora, Pythium spp. It was
only recommended for ornamental crops, mainly as a protective fungicide.
Formulation types SL (hydrochloride).
450
prothiocarb; prothiocarb hydrochloride
PRODUCTS:
Discontinued products Dynone* (Schering); Previcur* (hydrochloride) (Schering).
ANALYSIS:
Product analysis by argentometric titration of the ethanethiol liberated by hydrolysis.
Residues determined by the fluorimetric measurement of the N,N-dimethylpropane-1,3-
diamine liberated by alkaline hydrolysis.
EHC 76 (1988) is a general review of thiocarbamates. EU Status (1107/2009) Not
Oral Hydrochloride: Acute oral LD50 for rats 1300, mice 6601200 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >1470, rabbits >980 (both as mg a.i. as
formulation/kg). NOEL (90 d) for rats 0.5 mg/kg diet, for dogs 1.8 mg/kg diet.
Toxicity Class WHO (a.i.) O ECClassification Xn; R22| N; R51, R53 (hydrochloride)
prothoate
S
P(OCH2CH3)2
O CH2 S
C
(CH3)2CHNH
IRAC1B
NOMENCLATURE:
Common name prothoate (BSI, E-ISO, (m) F-ISO)
IUPACname O,O-diethyl S-isopropylcarbamoylmethyl phosphorodithioate;
2-diethoxyphosphinothioylthio-N-isopropylacetamide
Chemical Abstracts name O,O-diethyl S-[2-[(1-methylethyl)amino]-2-oxoethyl]
phosphorodithioate Other names trimethoate CASRN[2275185]
ECno2188932 DevelopmentcodesE.I. 18 682 (Cyanamid); L 343 (Montedison)
SmilescodeCCOP(=S)(OCC)SCC(=O)NC(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 285.4 M.f. C9H20NO3PS2 Form Colourless crystals with a camphor-like odour;
(tech. is an amber to yellow semi-solid). M.p.28.5C; (tech.: 2124C) V.p. 13 mPa
(40C) S.g./density 1.151 (32C) Solubility In water 2.5 g/l (20C, tech.). Miscible
with most organic solvents e.g. hexane, cyclohexane, higher petroleum FRACtions <30,
light petroleum <20, glycerol <10 (all in g/kg, 20C). Stability Stable at 4.0<pH<8.2, but
decomposed at 50C inc.48 h at pH 9.2. Tech. is stable to light and at 60C. F.p. 160C
prothoate 451
COMMERCIALISATION:
History Insecticide reported (Ital. Agric., 1955, 99, 747). Discovered by American
Cyanamid Co. and later introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
Patents US 2494283 (to Cyanamid); GB 791824 (to Montedison)
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic acaricide and
insecticide with contact and stomach action. Uses Control of mites, aphids, thrips, Lace
bugs, and other sucking insect pests on a range of crops, including fruit trees, citrus,
vegetables, cotton, ornamentals, sugar beet, sugar cane, tobacco, and vines.
Formulation types EC; WP; SL; DP; GR . Compatibility Not compatible with highly
alkaline materials.
PRODUCTS:
Discontinued products Fac* (Agrimont); Discontinuedmixtures Erysit Super*
(+chlorfenson) (Schering); Fac Super* (+chlorfenson) (Sopra).
ANALYSIS:
Product analysis by glc (B. Bazzi, Anal. Methods Pestic. Plant Growth Regul., 1976, 8, 213).
Residues on crops are determined by glc (B. Bazzi, loc. cit.; B. Bazzi et al., Pestic. Sci., 1974, 5,
511).
Oral Acute oral LD50 for male rats 8.0, female rats 8.9, mice 19.820.3 mg/kg.
Skin and eye Acute percutaneous LD50 for rats 655, rabbits 100200 mg/kg.
Inhalation LC50 (4 h) for rats 0.0029 mg/l air. NOEL (90 d) for rats 0.5 mg/kg daily, for
mice 1 mg/kg daily. Toxicity Class WHO (a.i.) Ia EPA (formulation) I
ECClassification T+; R27/28| R52, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 22.5 mg/kg, pheasants 18.8 mg/kg, wild ducks
11.9 mg/kg. Fish LC50 (96 h) for goldfish 33, trout 20, guppies 14 mg/l. Bees Dangerous to
bees.
proxan; proxan-sodium
Herbicide
NOMENCLATURE:
Common name proxan (E-ISO from 1990, BSI, Canada, New Zealand); proxane ((m)
F-ISO from 1990); IPX (WSSA)
IUPACname O-isopropyl hydrogen dithiocarbonate
452 proxan; proxan-sodium

Chemical Abstracts name O-(1-methylethyl) hydrogen carbonodithioate

CASRN[108258] proxan; [140932] proxan-sodium ECno2054435 sodium salt
PHYSICAL CHEMISTRY:
Mol. wt. 136.2; (sodium salt 158.2) M.f. C4H8OS2; (sodium salt C4H7NaOS2)
COMMERCIALISATION:
History Herbicide reported by L. L. Baumgartner & B. Wolf (Contrib. Boyce Thompson
Inst., 1949, 15, 403). Introduced by Goodrich Chemical Co.
PRODUCTS:
Discontinued products Goodriten.i.x.* (Goodrich).
Toxicity Class WHO (a.i.) O ECClassification Xn; R22| Xi; R38| N; R51, R53 (sodium
salt)
proximpham
Herbicide
N
O N
H
NOMENCLATURE:
Chemical Abstracts name 2-propanone O-[(phenylamino)carbonyl]oxime
CASRN[2828424] SmilescodeCC(=NOC(=O)Nc1ccccc1)C
PHYSICAL CHEMISTRY: Mol. wt. 192.2 M.f. C10H12N2O2 Form Colourless crystals.
M.p.109.5C V.p. 6.7 101 mPa (20C) Henry 2.58 104 Pa m3 mol1 (20C, calc.)
S.g./density 1.02 Solubility In water 500 mg/l (20C). Readily soluble in common
organic solvents, e.g. in methanol 43, DMF 41, ethanol 36, acetone 35, benzene 34, toluene
9, diethyl ether 5 (g/100g). Practically insoluble in hexane. Stability Stable up toc.90C.
In acidic media, hydrolysed to aniline and diphenylurea; in alkaline media, hydrolysed to
diphenyl urea and acetone oxime; in neutral aqueous solution, DT50 13 d.
COMMERCIALISATION:
APPLICATIONS: Uses Selective pre-emergence or pre-planting control of annual
weeds in beet crops,corn salad, lettuce and spinach as well as in the seeding of Scots pine
and spruce. Only used in mixed formulations.
ANALYSIS:
PRODUCTS: determined by gc with FID (D. Spengler & A. Jumar, Arch. Pflanzenschutz
1969, 5, 445) or titration of the iodine liberated by acid hydrolysis in the presence of
proximpham 453
iodide. Residues in soil by extraction with acetone, isolation and separation from other
herbicides by tlc, saponification with semi-concentrated sulfuric acid, diazotisation,
coupling with N-(1-naphthyl)ethylenediamine dihydrochloride, and spectrophotometric
measurement of the extinction at 550 nm (D. Spengler & A. Jumar, J. Chromatogr. 1970, 49,
329).
Oral Acute oral LD50 for rats 1540, mice 1300 mg/kg. NOEL (90 d) for rats 100 mg/kg.
ECOTOXICOLOGY:
Fish LC50 (48 h) for guppies 93 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In soil, there is partly microbial, partly hydrolytic degradation; DT50
710 d. Aniline is not found.
prynachlor
Herbicide
NOMENCLATURE:
Common name prynachlore ((m) F-ISO); prynachlor (BSI, E-ISO, ANSI, WSSA)
IUPACname 2-chloro-N-(1-methylprop-2-ynyl)acetanilide
Chemical Abstracts name 2-chloro-N-(1-methyl-2-propynyl)-N-
phenylacetamide CASRN[21267721] DevelopmentcodesBAS 290H (BASF)
SmilescodeCC(C#C)N(C(=O)CCl)c1ccccc1
PHYSICAL CHEMISTRY:
Mol. wt. 221.7 M.f. C12H12ClNO
COMMERCIALISATION:
History Herbicide developed by BASF AG.
PRODUCTS:
Discontinued products Basamaize* (BASF).
PT807
Most data here are taken from the EPA Fact Sheet.
NOMENCLATURE:
Chemical Abstracts name N,N-diethyl-2-(4-methylbenzyloxy)ethylamine hydrochloride
Other names MBTA CASRN[274671613] DevelopmentcodesPT807
PHYSICAL CHEMISTRY:
Composition Except where stated otherwise, data are for the hydrochloride salt.
454 PT807
Mol. wt. 221.3 M.f. C14H23NO (free base) Form Colourless slightly viscous liquid.
B.p. 105.91.5C V.p. 1.19 10-2 mPa (EPA Fact Sheet) Kow logP <0 (pH 5 and 7),
2.02.4 (pH 9) (EPA Fact Sheet) S.g./density 1.0596 Solubility Miscible with water (pH
59). Miscible with acetonitrile, methanol, dichloromethane and octanol (25C).
Stability Stable to hydrolysis. pKa 9.55
COMMERCIALISATION:
History Plant growth regulator. First registered in USA in 1999; registration cancelled in
2004.
Manufacturers GMJA
APPLICATIONS:
ModeofactionSystemic. Uses Promotes sugar accumulation in processing oranges and
shortens the time to maturation; applied at 0.013 lb/a. Formulation types SC.
PRODUCTS:
Discontinued products Ecolyst* (GMJA).
EPA Fact Sheet, Jan. 2000.
Oral Acute oral LD50 for rats 531 mg/kg. Skin and eye Slight to moderate eye irritant;
not a skin irritant. Not a skin sensitiser. NOEL Acute neurotoxicity NOAEL for rats 50
mg/kg daily. Reproductive NOAEL for rats 14 mg/kg daily. (EPA Fact Sheet).
ADI/RfD (EPA) aRfD 0.5, cRfD 0.14 mg/kg b.w. [2000].
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 765 mg/kg. Dietary LC50 (8 d) for bobwhite
quail and mallard ducks >5600 ppm. Fish LC50 (96 h) for rainbow trout 6.7, bluegill sunfish
>12.6, sheepshead minnows 16 mg/l. Daphnia LC50 (24 h) 24 mg/l. Algae IC50 (96 h) for
Pseudokirchneriella subcapitata 0.40, Skeletonema costatum 0.119, Navicula pelliculosa
0.88 mg/l. Other aquatic spp. EC50 (96 h) for eastern oysters 7.0, mysid shrimps 20 mg/l.
IC50 (96 h) for Lemma gibba >116 mg/l. Bees LD50 for honeybees >25 g/bee.
ENVIRONMENTAL FATE:
Animals After administration to rats, rapidly metabolised and excreted, primarily in the
urine; only minor amounts of parent were identified in urine and faeces. The primary
metabolite was a carboxylic acid metabolite, which then undergoes conjugation to
glucuronic acid, or hydroxylation on the alkyl portion of the molecule.
Soil/Environment Stable to photolysis. Soil DT50 (aerobic metabolism) 335 d; the
primary degradation pathway is aerobic degradation to CO2. Persistent, moderately mobile
to immobile; Koc 28511000.
PT807 455
pydanon
H
N O
HN
O OH
OH
O
NOMENCLATURE:
Common name pydanon (BSI, E-ISO, (m) F-ISO)
IUPACname ()-hexahydro-4-hydroxy-3,6-dioxopyridazin-4-ylacetic acid
Chemical Abstracts name hexahydro-4-hydroxy-3,6-dioxo-4-pyridazineacetic acid
CASRN[22571079] unstated stereochemistry DevelopmentcodesH 1244
SmilescodeOC(=O)CC1(O)CC(=O)NNC1=O
PHYSICAL CHEMISTRY:
Mol. wt. 188.1 M.f. C6H8N2O5 M.p.98C V.p. Negligible (room temperature) Solubility
Readily soluble in water.
COMMERCIALISATION:
History Plant growth regulator developed by C. F. Spiess & Sohn.
APPLICATIONS:
ModeofactionPlant growth regulator. rapidly absorbed by leaves and roots and
translocated acropetally and basipetally. Uses Applied to young plants to delay general
development for 13 w. Applied before bud break, causing retardation of blossom for
12 w. Also prevents chlorosis of seedlings inside containers.
Oral Oral LD50 for mice 1000 mg/kg. Toxicity Class WHO (a.i.) O
pyflubmide
C H3
O F3 C
N
CF3
N
N
H 3C O
C H3
C H3
O C H3
NOMENCLATURE: H 3C
H 3C
CH 3
Common name pyflubumide (pa ISO)
IUPACname 3-isobutyl-N-isobutyryl-1,3,5-trimethyl-4-[2,2,2-trifluoro-1-methoxy-1-
(trifluoromethyl)ethyl]pyrazole-4-carboxanilide
456 pyflubmide
Chemical Abstracts name 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-

methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-
pyrazole-4-carboxamide CASRN[926914558] DevelopmentcodesNNI0711
SmilescodeCc1c(c(n(n1)C)C)C(=O)N(c2ccc(c(c2)CC(C)C)C(C(F)(F)F)(C(F)(F)F)OC)
C(=O)C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 535.52 M.f. C25H31F6N3O3
pyracarbolid
Fungicide
NOMENCLATURE:
Common name pyracarbolide ((m) F-ISO); pyracarbolid (BSI, E-ISO)
IUPACname 3,4-dihydro-6-methyl-2H-pyran-5-carboxanilide
Chemical Abstracts name 3,4-dihydro-6-methyl-N-phenyl-2H-pyran-5-carboxamide
CASRN[24691767] ECno2464194 DevelopmentcodesHoe 13 764; Hoe 02
989 *; Hoe 6052 *; Hoe 6053 * SmilescodeCC1=C(CCCO1)C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. is 98%. Mol. wt. 217.3 M.f. C13H15NO2 Form Colourless
solid. M.p.110111C V.p. 0.016 mPa (25C) Solubility In water 0.6 g/l (40C). In
chloroform 366, ethanol 89, ethyl acetate 86, hexane 0.1, xylene 13 (all in g/l, 25C).
Stability Stable to light and heat and in alkaline media, but decomposed by acids.
COMMERCIALISATION:
History Fungicide reported by H. Stingle etal. (Int. Congr. Plant Prot., 7th, Paris, 1970, p.
205 (Abstr.)) and B. Jank & F. Grossman (Pestic. Sci., 1971, 2, 43). Introduced by Hoechst AG.
Patents DE 1668899; GB 1194526
APPLICATIONS:
ModeofactionSystemic fungicide, absorbed by plants via roots and leaves.
Uses Effective against Basidiomycetes. It controls Rusts (Uredinales), Smuts (Ustilaginales),
and Damping-off disease caused by Thanatephorus cucumeris (Rhizoctonia solani). It is
used in bean, cereal, coffee, and tea crops. Rates and concentrations vary considerably
depending on disease/crop combination and formulation. Formulation types SC. WP;
Seed treatment.
PRODUCTS:
Discontinued products Sicarol* (Hoechst).
ANALYSIS:
Product analysis is by titration. Residues may be determined by colorimetric methods.
pyracarbolid 457
Oral Acute oral LD50 for female rats >15000 mg (in starch mucilage)/kg.
Skin and eye Acute percutaneous LD50 for female rats >1000 mg/kg. NOEL (2 y) for rats
400, dogs 1600 mg/kg diet. Other Acute i.p. LD50 for female rats 1600 mg/kg.
Toxicity Class WHO (a.i.) U ECClassification R52, R53
ECOTOXICOLOGY:
Fish LC50 (96 h) for carp 42.3, rainbow trout 45.5 mg/l.
pyresmethrin
Insecticide
IRAC3
NOMENCLATURE:
Common name pyresm(thrine) ((f) F-ISO); pyresmethrin (BSI, E-ISO)
IUPACname 5-benzyl-3-furylmethyl (E)-(1R)-trans-3-(2-methoxycarbonylprop-1-
enyl)-2,2-dimethylcyclopropanecarboxylate; 5-benzyl-3-furylmethyl (E)-(1R,3R)-3-(2-
methoxycarbonylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name [1R-[1,3(E)]]-[5-(phenylmethyl)-3-furanyl]methyl
3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
CASRN[24624586], formerly [56194684] and [20425392]
DevelopmentcodesNRDC 106; RU-12061
SmilescodeCOC(=O)C(=CC1C(C(=O)OCc2coc(Cc3ccccc3)c2)C1(C)C)C
COMMERCIALISATION:
History Insecticide discovered by M. Elliott et al.
APPLICATIONS:
pyriclor
Herbicide
NOMENCLATURE:
Common name pyriclor (WSSA)
IUPACname 2,3,5-trichloropyridin-4-ol
Chemical Abstracts name 2,3,5-trichloro-4-pyridinol CASRN[1970407]
SmilescodeOc1c(Cl)cnc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 198.4 M.f. C5H2Cl3NO
458 pyriclor
COMMERCIALISATION:
History Herbicide reported by M. J. Huraux & H. M. Lawson (Symp. New Herbic., 2nd, 1965,
p. 269). Introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
ModeofactionTranslocated herbicide.
PRODUCTS:
Discontinued products Daxtron* (Dow).
pyridafol
Herbicide
Cl N
N
OH
HRACC3; phenylpyridazine
NOMENCLATURE:
Common name pyridafol (BSI, E-ISO, (m) F-ISO)
IUPACname 6-chloro-3-phenylpyridazin-4-ol
Chemical Abstracts name 6-chloro-3-phenyl-4-pyridazinol CASRN[40020017]
ECno2547521 DevelopmentcodesNOA 402 989; SAN 1367H
PHYSICAL CHEMISTRY:
Mol. wt. 206.6 M.f. C10H7ClN2O
COMMERCIALISATION:
History Herbicide evaluated by Novartis Crop Protection AG.
APPLICATIONS:
receptor site.
EU Status (1107/2009) Not approved, application withdrawn.
ENVIRONMENTAL FATE:
Soil/Environment In soil, formed as a degradate of pyridate, q.v. for details.
pyridafol 459
pyridinitril
Fungicide
NOMENCLATURE:
Common name pyridinitril (BSI, E-ISO); DDPP (JMAF); pyridinitrile ((m) F-ISO)
IUPACname 2,6-dichloro-4-phenylpyridine-3,5-dicarbonitrile
Chemical Abstracts name 2,6-dichloro-4-phenyl-3,5-pyridinedicarbonitrile
CASRN[1086028] DevelopmentcodesIT 3296
SmilescodeClc1nc(Cl)c(C#N)c(c1C#N)c2ccccc2
PHYSICAL CHEMISTRY: Mol. wt. 274.1 M.f. C13H5Cl2N3
COMMERCIALISATION:
History Fungicide reported by G. Mohr etal. (Meded. Rijksfac. Landbouwwet. Gent, 1968,
33, 1293). Introduced by E. Merck (later Shell Agrar GmbH).
APPLICATIONS:
PRODUCTS:
Discontinuedmixtures Ciluan* (+captan) (E. Merck).
pyrifenox
Fungicide
Cl
CH2
N C Cl
N
CH3O
FRAC3, G1; SBI Class I, DMI: pyridine
NOMENCLATURE:
Common name pyrif(nox) ((m) F-ISO); pyrifenox (BSI, ANSI, E-ISO)
IUPACname 2,4-dichloro-2-(3-pyridyl)acetophenone (E,Z)-O-methyloxime
Chemical Abstracts name 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)ethanone
O-methyloxime CASRN[88283414] DevelopmentcodesRo 151297;
ACR 3651 A (both Dr Maag); CGA 179945 (Ciba); NRK-297 (Nippon Kayaku)
SmilescodeCON=C(Cc1cccnc1)c2ccc(Cl)cc2Cl
PHYSICAL CHEMISTRY:
Composition A mixture of (E)- and (Z)- isomers. Mol. wt. 295.2 M.f. C14H12Cl2N2O
460 pyrifenox
Form Pale yellow, viscous liquid, with a slightly sweet odour. B.p. 212.1C V.p. 1.7 mPa
(25C) Kow logP = 3.4 (pH 5.0), 3.7 (pH 7.0), 3.7 (pH 9.0) (all 25C) S.g./density 1.28
(20C) Solubility In water 300 (pH 5.0), 150 (pH 6.7), 130 (pH 9.0) (all in mg/l, 25C).
In n-hexane 210 g/l (25C). Completely miscible with ethanol, acetone, toluene and
n-octanol. Stability Stable for >3 years in a closed container at room temperature. Stable
to uv light and to hydrolysis in water (pH 3, 7, 9; 50C). pKa 4.61, weak base F.p. 106C
(1013 mbar)
COMMERCIALISATION:
History Fungicide reported by P. Zobrist etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1986,
1, 47). Introduced by Dr R Maag Ltd and first marketed in 1986. Patents EP 49854
Manufacturers Syngenta
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor. ModeofactionSystemic fungicide
with protective and curative action. Absorbed by the leaves and roots, and translocated
acropetally. Uses Systemic Fungicide used, at 40150 g/ha, for the control of powdery
mildew, scab and other pathogenic Ascomycetes, Basidiomycetes and Deuteromycetes on
grapes, cucurbits, pome fruit, stone fruit, peanuts, sugar beet, ornamentals and vegetables.
Formulation types EC; WG; WP.
PRODUCTS:
Discontinued products Corado* (Ciba); Corona* (Syngenta); Curado* (Ciba);
Dorado* (Syngenta); Podigrol* (Syngenta); Discontinuedmixtures Furado*
(+mancozeb) (Ciba); Rondo* (+captan) (Syngenta).
ANALYSIS:
Product analysis by tlc, glc, or hplc; glc with FID is recommended. Residues determined
by lc, glc or hplc. See R. P. Hanni & A. J. Schuler, in Comp. Anal. Profiles, Chapt. 3. Details also
available from Syngenta.
J. Pestic. Sci., 1991, 16, 355359. EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD50 for rats 2912, mice >2000 mg/kg. Skin and eye Acute percutaneous
LD50 for rats >5000 mg/kg. Weak irritant to skin (humans); non-irritant to eyes (rabbits).
Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >2048 mg/m3 air.
NOEL (2 y) for rats 15 mg/kg b.w. daily; (1.5 y) for mice 45 mg/kg b.w. daily; (1 y) for dogs
10 mg/kg b.w.. daily. ADI/RfD (BfR) 0.09 mg/kg b.w. [1991]; (EPA) 0.01 mg/kg b.w. [1987].
Other Not mutagenic, not teratogenic, and not oncogenic. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD50 (14 d) for mallard ducks and bobwhite quail >2000 mg/kg.
Fish LC50 (96 h) for rainbow trout 7.1, mirror carp 12.2, bluegill sunfish 6.6 mg/l.
Daphnia EC50 (48 h) 3.6 mg/l. Algae EC50 (96 h) for Scenedesmus subspicatus 0.095
mg/l. Bees LD50 (48 h) (oral) 59 g/bee; (contact) 70 g/bee. Worms LC50 (14 d)
pyrifenox 461
for earthworms 733 mg/kg. Other beneficial 200 g/l EC formulation harmless to
Typhlodromus pyri and Orius insidiosus; slightly toxic to Coccinella septempunctata and
Trichogramma cacoeciae (IOBC).
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, pyrifenox is rapidly absorbed, metabolised
and excreted in the urine and faeces. There are no indications of bioretention in tissue
or organs. Plants Relatively rapid degradation in plants. DT50 in peanut leaves 4 d, apple
leaves 3 d, apple fruit 9 d. The main degradation pathway is by hydrolysis and elimination
of the oxime group. Soil/Environment Moderate soil mobility, no tendency toward
bioaccumulation, little potential for environmental persistence, and fairly rapid dissipation
in plants, soil, water and animals. See R. P. Hanni & A. J. Schuler, in Comp. Anal. Profiles,
Chapt. 3. DT50 in soil 50120 d, Koc 980 ml/g soil.
pyriminostrobin
Acaricide
CF3
CH 3
H O NH
H 3C
O O N N
O
Cl
Cl
NOMENCLATURE:
Common name pyriminostrobin (pa ISO)
IUPACname methyl (E)-2-{-[2-(2,4-dichloroanilino)-6-(trifluoromethyl)pyrimidin-4-
yloxy]-o-tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-
(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]--(methoxymethylene)benzeneacetate
SmilescodeInChI=1S/C23H18Cl2F3N3O4/c1-33-12-16(21(32)34-2)15-6-4-3-5-
13(15)11-35-20-1019(23(26,27)28)30-22(31-20)29-18-8-7-14(24)9-17(18)25/h3-
10,12H,11H2,1-2H3,(H,29,30,31)/b16-12+
PHYSICAL CHEMISTRY:
Mol. wt. 528.31 M.f. C23H18Cl2F3N3O4
462 pyriminostrobin
pyrimitate
IRAC1B
NOMENCLATURE:
Common name pyrimitate (BSI, E-ISO, (m) F-ISO, BAN (from 1985)); pyrimithate* (BAN
before 1985)
IUPACname O-2-dimethylamino-6-methylpyrimidin-4-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[2-(dimethylamino)-6-methyl-4-pyrimidinyl] O,O-
diethyl phosphorothioate CASRN[5221498] DevelopmentcodesICI 29 661
SmilescodeCCOP(=S)(OCC)Oc1cc(C)nc(n1)N(C)C
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Veterinary insecticide and acaricide introduced by ICI Pharmaceuticals Division.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses For veterinary use.
PRODUCTS:
Discontinued products Diothyl* (ICI).
pyrinuron
Rodenticide
NOMENCLATURE:
Common name pyrinuron (BSI, E-ISO, (m) F-ISO, ANSI); piriminil (JMAF)
IUPACname 1-(4-nitrophenyl)-3-(3-pyridylmethyl)urea
Chemical Abstracts name N-(4-nitrophenyl)-N-(3-pyridinylmethyl)urea
CASRN[53558251] DevelopmentcodesRH-787
Smilescode[O-][N+](=O)c1ccc(NC(=O)NCc2cccnc2)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 272.3 M.f. C13H12N4O3
COMMERCIALISATION:
History Rodenticide evaluated by Rohm & Haas Co.
PRODUCTS:
Discontinued products Vacor* (Rohm & Haas).
pyrinuron 463
pyriprole
Insecticide
N
F F
S
N
Cl N
N
Cl H
N
F
F
NOMENCLATURE: F
Common name pyriprole (BSI, E-ISO, (m) F-ISO)
IUPACname 1-(2,6-dichloro-,,-trifluoro-p-tolyl)-4-(difluoromethylthio)-5-[(2-
pyridylmethyl)amino]pyrazole-3-carbonitrile
Chemical Abstracts name 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-
4-[(difluoromethyl)thio]-5-[(2-pyridinylmethyl)amino]-1H-pyrazole-3-
carbonitrile CASRN[394730713] DevelopmentcodesV3086
SmilescodeN#CC1=NN(C2=C(Cl)C=C(C(F)(F)F)C=C2Cl)
C(NCC3=NC=CC=C3)=C1SC(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 494.3 M.f. C18H10Cl2F5N5S
COMMERCIALISATION:
History Under development as an insecticide. Patents EP 1310497; US 7371768.
APPLICATIONS: Uses Control of Lepidoptera and Coleoptera.
pyrisoxazole
Fungicide
N Cl
O
H 3C N
H 3C
FRAC3, G1; SBI Class I, DMI: pyridine

NOMENCLATURE:
Common name pyrisoxazole (pa ISO)
464 pyrisoxazole
IUPACname 3-[(3R,5RS)-5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine
Chemical Abstracts name 3-[(3R)-5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]
pyridine CASRN[291771998] (3R,5R)- isomer; [291771830] (3R,5S)- isomer
DevelopmentcodesSYP-48
SmilescodeC[C@@]1(CC(ON1C)c2ccc(cc2)Cl)c3cccnc3
PHYSICAL CHEMISTRY:
pyroxychlor
Fungicide
NOMENCLATURE:
Common name pyroxychlor (BSI, E-ISO, ANSI); pyroxychlore ((m) F-ISO)
IUPACname 2-chloro-6-methoxy-4-trichloromethylpyridine; 6-chloro-4-trichloromethyl-
2-pyridyl methyl ether
Chemical Abstracts name 2-chloro-6-methoxy-4-(trichloromethyl)pyridine
SmilescodeCOc1cc(cc(Cl)n1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 260.9 M.f. C7H5Cl4NO
COMMERCIALISATION:
History Fungicide evaluated by Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Lorvek* (Dow); Nurelle* (Dow).
pyroxyfur
Fungicide
NOMENCLATURE:
Common name pyroxyfur (BSI, ANSI, E-ISO, (m) F-ISO)
IUPACname 6-chloro-4-trichloromethyl-2-pyridyl furfuryl ether
Chemical Abstracts name 2-chloro-6-(2-furanylmethoxy)-4-(trichloromethyl)
pyridine CASRN[70166482] DevelopmentcodesDowco 444
SmilescodeClc1cc(cc(OCc2ccco2)n1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 327.0 M.f. C11H7Cl4NO2
COMMERCIALISATION:
History Fungicide evaluated by Dow Chemical Co. (later DowElanco).
pyroxyfur 465
PRODUCTS:
Discontinued products Grandstand* (Dow).
N-pyrrolidinosuccinamic acid
NOMENCLATURE:
IUPACname N-pyrrolidinosuccinamic acid
Chemical Abstracts name 4-oxo-4-(1-pyrrolidinylamino)butanoic acid
CASRN[23744050] DevelopmentcodesF 529
SmilescodeOC(=O)CCC(=O)NN1CCCC1
PHYSICAL CHEMISTRY:
Mol. wt. 186.2 M.f. C8H14N2O3
COMMERCIALISATION:
History Plant growth regulator evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
ModeofactionPlant growth retardant.
PRODUCTS:
Discontinued products FFive* (Uniroyal).
quinalphos-methyl
Insecticide
IRAC1B
NOMENCLATURE:
Common name quinalphos-methyl (BSI, E-ISO, (m) F-ISO); chinalphos-m(thyl) ((m)
France)
IUPACname O,O-dimethyl O-quinoxalin-2-yl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-2-quinoxalinyl phosphorothioate
CASRN[13593083] DevelopmentcodesSAN 52 056I
SmilescodeCOP(=S)(OC)Oc1cnc2ccccc2n1
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG. For quinalphos, see Main entries.
APPLICATIONS:
466 quinalphos-methyl
quinazamid
Fungicide
NOMENCLATURE:
Common name quinazamid (BSI, E-ISO); quinazamide ((m) F-ISO)
IUPACname p-benzoquinone monosemicarbazone
Chemical Abstracts name 2-(4-oxo-2,5-cyclohexadien-1-ylidene)hydrazinecarboxamide
CASRN[61566210] DevelopmentcodesRD 8684; BTS 8684
SmilescodeNC(=O)NN=C1C=CC(=O)C=C1
PHYSICAL CHEMISTRY:
Mol. wt. 165.2 M.f. C7H7N3O2
COMMERCIALISATION:
History Fungicide evaluated by Boots Co., Ltd (later Schering Agrochemicals).
quinconazole
Fungicide
NOMENCLATURE:
Common name quinconazole (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one
Chemical Abstracts name 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-
4(3H)-quinazolinone CASRN[103970758] DevelopmentcodesSN 539 865
SmilescodeClc1ccc(c(Cl)c1)n2c(nc3ccccc3c2=O)n4cncn4
PHYSICAL CHEMISTRY:
Mol. wt. 358.2 M.f. C16H9Cl2N5O
COMMERCIALISATION:
History Fungicide reported by C. R. Leake (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1,
343). Evaluated by Schering AG.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor.
quinonamid
Algicide
NOMENCLATURE:
Common name quinonamid (BSI, E-ISO); quinonamide ((m) F-ISO)
IUPACname 2,2-dichloro-N-(3-chloro-1,4-naphthoquinon-2-yl)acetamide
Chemical Abstracts name 2,2-dichloro-N-(3-chloro-1,4-dihydro-1,4-dioxo-2-
quinonamid 467
naphthalenyl)acetamide CASRN[27541884] DevelopmentcodesHoe 02 997

SmilescodeClC(Cl)C(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
Composition Tech. is 97%. Mol. wt. 318.5 M.f. C12H6Cl3NO3 Form Yellow needles.
M.p.214216C V.p. 0.011 mPa (20C) Solubility In water 3.0 (pH 4.6), 60 (pH 7)
(both mg/l, 23C). In acetonec.7, ethanolc.3, hexane 0.04, xylene 8 (all in g/l, 20C).
Stability Decomposed by acid or alkali.
COMMERCIALISATION:
History Algicide reported by P. Hartz etal. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1972,
37, 699). Introduced by Hoechst AG. Patents DE 1768447; GB 1263625
APPLICATIONS: Uses Effective against algae in the open as well as algae and mosses
under glass. It could be used as a seed treatment or spray for control of algae in paddies, as
a dip for clay pots, and for treating benches, etc., in greenhouses.
PRODUCTS:
Discontinued products Alginex* (Hoechst); Nosprasit* (Hoechst).
ANALYSIS:
Product and residue analysis is by glc.
Oral Acute oral LD50 for rats 1170015000 mg/kg. NOEL (90 d) for rats 2000 mg/kg
diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD50 for Japanese quail 1113615542 mg/kg (depending on carrier and
sex). Fish LC50 (96 h) for rainbow trout 0.45 mg/l.
quinothion
Insecticide
IRAC1B
NOMENCLATURE:
Common name quinothion (BSI)
IUPACname O,O-diethyl O-2-methyl-4-quinolyl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(2-methyl-4-quinolinyl) phosphorothioate
CASRN[22439403] SmilescodeCCOP(=S)(OCC)Oc1cc(C)nc2ccccc12
PHYSICAL CHEMISTRY:
Mol. wt. 311.3 M.f. C14H18NO3PS
COMMERCIALISATION:
468 quinothion
APPLICATIONS:
quintiofos
Insecticide
IRAC1B
NOMENCLATURE:
Common name quintiofos (BSI, E-ISO, (m) F-ISO, BAN)
IUPACname O-ethyl O-8-quinolyl phenylphosphonothioate
Chemical Abstracts name O-ethyl O-8-quinolinyl phenylphosphonothioate
CASRN[1776836] DevelopmentcodesBAY 9037
SmilescodeCCOP(=S)(Oc1cccc2cccnc12)c3ccccc3
PHYSICAL CHEMISTRY:
Mol. wt. 329.4 M.f. C17H16NO2PS
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Bacdip* (Bayer).
R-1492
IRAC1B
NOMENCLATURE:
IUPACname S-4-chlorophenylthiomethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[[(4-chlorophenyl)thio]methyl] O,O-dimethyl
phosphorodithioate Other names methylcarbophenothione; methyl carbophenothion
CASRN[953173] DevelopmentcodesR-1492 (Stauffer); G-29288 (Geigy)
SmilescodeCOP(=S)(OC)SCSc1ccc(Cl)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 314.8 M.f. C9H12ClO2PS3 Form Light yellow to amber liquid with a moderate
mercaptan odour. M.p.c. 18C V.p. 400 mPa (25C) S.g./density 1.341.35 (20C)
Solubility In water c.1 mg/l (room temperature). Miscible with most organic solvents.
Stability Moderately stable to heat and resistant to hydrolysis.
R-1492 469
COMMERCIALISATION:
History Insecticide and acaricide reported by J. A. Harding (J. Econ. Entomol., 1959, 52,
1219). Introduced by Stauffer Chemical Co. (later ICI Americas). Patents US 2793224.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic. Uses Acaricide
similar in spectrum of activity to its analogue carbophenothion (q.v.), but more effective
against cotton boll weevil; applied at 50100 g/100 l.
PRODUCTS:
Discontinued products Methyl Trithion* (Stauffer); TriMe* (Stauffer).
ANALYSIS:
Product analysis by uv absorption methods, or by glc. For residues, see G. H. Batchelder et
al., Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 313; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 443.
ECClassification T; R24/25| N; R50, R53| concn. dep.
RA-17
Acaricide
S
P(OCH2CH3)2
CH3CH2 N
CH2CON(CH2CH2CH3)2
IRAC1B
NOMENCLATURE:
IUPACname N2-diethoxyphosphinothioyl-N2-ethyl-N1,N1-dipropylglycinamide
Chemical Abstracts name O,O-diethyl [2-(dipropylamino)-2-oxoethyl]
ethylphosphororamidothioate Other names phosglycin CASRN[105084660]
DevelopmentcodesRA-17 (MV)
SmilescodeCCCN(CCC)C(=O)CN(CC)P(=S)(OCC)OCC
PHYSICAL CHEMISTRY:
Mol. wt. 338.4 M.f. C14H31N2O3PS Form Solid. M.p.34C V.p. 1.8 mPa (25C) Kow
logP = 3.9 Solubility In water 140 mg/l (20C). In acetone, benzene, chloroform,
dichloromethane, ethanol, hexane >200 mg/l (20C).
Stability Stable up to 180C. Degraded photochemically on silica gel plate (DT50 18 h).
COMMERCIALISATION:
History Acaricide reported by K. Balogh & G. Tarpai (6th Int. Congr. Pestic. Chem., 1986).
Introduced in Hungary (1987) by szakmagyarorszgi Vegyimvek. Patents BE 903304; HU
2164940
470 RA-17
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Effective against adults and larvae of
phytophagous mites in apples (2.5 kg/ha), citrus (12 hg/ha) and grapes (23 kg/ha).
PRODUCTS:
Discontinued products Alkatox* (Sagrochem).
ANALYSIS:
Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Inhalation Non-toxic to
rats at 0.59 mg/l air.
ECOTOXICOLOGY:
Fish LC50 for carp 9.47, grass carp 12.5 mg/l, for sheat fish 12 mg a.i. (as EC)/l.
rabenzazole
Fungicide
NOMENCLATURE:
Common name rabenzazole (BSI, E-ISO, (m) F-ISO)
IUPACname 2-(3,5-dimethylpyrazol-1-yl)benzimidazole
Chemical Abstracts name 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1H-benzimidazole
CASRN[40341046] SmilescodeCc1cc(C)n(n1)c2nc3ccccc3[nH]2
PHYSICAL CHEMISTRY:
Mol. wt. 212.3 M.f. C12H12N4
COMMERCIALISATION:
History Fungicide reported by W. Specht & M. Tillkes (Pflanz.-Nachr. Bayer (Engl. Ed.), 1980,
33, 61). Introduced by Bayer AG.
PRODUCTS:
Discontinued products Ciriom* (Bayer); Discontinuedmixtures Ciriom F*
(+fuberidazole) (Bayer).
rabenzazole 471
rescalure
Attractant
C H2 CH 3 O
H 3C O C H3
C H2
NOMENCLATURE:
Common name rescalure (pa ISO)
IUPACname (3RS,6RS;3RS,6SR)-6-isopropenyl-3-methyldec-9-en-1-yl acetate
Chemical Abstracts name 3-methyl-6-(1-methylethenyl)-9-decen-1-yl acetate
CASRN[64309031] SmilescodeCC(CCC(CCC=C)C(=C)C)CCOC(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 252.39 M.f. C16H28O2
RH 5849
Insecticide
O
C(CH3)3
HN N
O
NOMENCLATURE:
IUPACname 2-benzoyl-1-tert-butylbenzohydrazide
Chemical Abstracts name benzoic acid 2-benzoyl-1-(1,1-dimethylethyl)hydrazide
CASRN[112225873] DevelopmentcodesRH-5849 (Rohm & Haas)
PHYSICAL CHEMISTRY:
Mol. wt. 296.4 M.f. C18H20N2O2 Form Colourless crystals. M.p.174176C
V.p. 0.24 mPa (25C) Kow logP = 2.326 Solubility In water c.50 mg/l. In
cyclohexanonec.50, mesityl oxidec.150 g/l. Stability Stable under normal storage
conditions.
COMMERCIALISATION:
History Insect growth regulator, of interest as the first non-steroidal ecdysone agonist,
reported by K. D. Wing (Science, 1988, 241, 467), K. D. Wing etal. (ibid., p. 470). Introduced
by Rohm & Haas Co. Patents EP 236618 Manufacturers Rohm & Haas; Zhejiang Heyi
472 RH 5849
APPLICATIONS:
Biochemistry Non-steroidal ecdysone agonist. ModeofactionInduces premature
moulting at any point in larval development. Inhibits feeding and oviposition. Uses Control
of colorado beetles on potatoes, pear leaf blister moths, leaf miners on apples and other
crops, gypsy moths, codling moths, Mexican bean beetles, cutWorms, rice stem borers,
ArmyWorms, boll weevils and houseflies. Formulation types SC. GR .
>5000 mg/kg. Not irritant to skin or eyes of rabbits. Other Not mutagenic in Ames assay.
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks and quail >5000 mg/kg diet. Fish LC50 (96 h)
for bluegill sunfish and trout >100 mg/l. Daphnia LC50 (48 h) 7 mg/l; for life cycle 0.50.7
mg/l. Bees LD50 (contact) >0.1 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment In silt loam DT50 27 d (23C).
rhodethanil
Herbicide
NOMENCLATURE:
Common name rhodethanil (BSI, E-ISO); rod(thanil) ((m) F-ISO)
IUPACname 3-chloro-4-ethylaminophenyl thiocyanate
Chemical Abstracts name 3-chloro-4-(ethylamino)phenyl thiocyanate
CASRN[3703466] DevelopmentcodesBAY 5396 b H; BAY 53 427
SmilescodeCCNc1ccc(SC#N)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 212.7 M.f. C9H9ClN2S
COMMERCIALISATION:
RU 25475
Insecticide
IRAC3
NOMENCLATURE:
IUPACname (S)--cyano-3-phenoxybenzyl (1R,3S)-[(RS)-1,2-dibromo-2,2-
dichloroethyl]-2,2-dimethylcyclopropanecarboxylate; Roth: (S)--cyano-3-phenoxybenzyl
(1R)-trans-3-((RS)-1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropanecarboxylate
RU 25475 473
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 3-(1,2-dibromo-2,2-

dichloroethyl)-2,2-dimethylcyclopropanecarboxylate Other names tralocythrin*
(unaccepted common name) CASRN[66841267] unstated stereochemistry
DevelopmentcodesRU 25475; HAG 106
SmilescodeCC1(C)C(C(Br)C(Cl)(Cl)Br)C1C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY:
Mol. wt. 576.1 M.f. C22H19Br2Cl2NO3
COMMERCIALISATION:
History Insecticide evaluated by Roussel Uclaf for use in cotton.
APPLICATIONS:
ryanodine
Insecticide
OH CH
CH3 OHHO
3
OH
CH3
HO O
CH3 H O O OH
CH3
NH

NOMENCLATURE:
Chemical Abstracts name (3S,4R,4aR,6S,6aS,7S,8R,8aS,8bR,9S,9aS)-dodecahydro-
4,6,7,8a,8b,9a-hexahydroxy-3,6a,9-trimethyl-7-(1-methylethyl)-6,9-methanobenzo[1,2]
pentaleno[1,6-bc]furan-8-yl 1H-pyrrole-2-carboxylate Other names ryania extract
CASRN[15662336] ryanodine, formerly [1361019], [1580069], [25800571]
and [15800609]; [94513550] 9,21-dehydroryanodine; [8047130] formerly ryania,
now a deleted number for ryanodine ECno2397322
SmilescodeCC(C)C1(O)C(OC(=O)c2ccc[nH]2)C3(O)C4(O)C1(C)C5(O)CC3(C)
C6(O)CCC(C)C(O)C46O5
PHYSICAL CHEMISTRY:
Composition The main toxicant of ryania, the ground stemwood of the shrub Ryania
speciosa; 9,21-dehydroryanodine and other ryanoids are also present in the crude plant
extract. Mol. wt. 493.6 M.f. C25H35NO9 M.p.219220C (decomp.) Solubility Soluble
in water, ethanol, acetone, diethyl ether, chloroform; almost insoluble in benzene, light
474 ryanodine
petroleum. Stability Relatively stable on exposure to light and air. Specific rotation []D25
+26
COMMERCIALISATION:
Production Extracted from the powdered stem of the tropical shrub Ryania speciosa.
History Insecticidal activity of ryania reported by B. E. Pepper & L. A. Carruth (J.
Econ. Entomol., 1945, 38, 59). Introduced by S. B. Penick & Co. Patents US 2400295
Manufacturers Dunhill
APPLICATIONS:
Biochemistry Thought to cause a release of calcium from the sarcoplasmic reticulum in
skeletal muscles fibers which in turn leads to sustained muscle contraction and paralysis.
ModeofactionActive by ingestion and by contact. Uses Ryania was used for control of
codling moth, European corn borer and citrus thrips in fruit and maize. Applied at 1072 kg
ryania/ha (20145 g alkaloid/ha). Formulation types WP.
PRODUCTS:
Discontinued products Natur-Gro R-50* (AgriSystems International); Natur-Gro
Triple Plus* (AgriSystems International); Ryan 50* (Dunhill); Ryania* (Penick); Rynotox*
(Penick).
ANALYSIS:
Product analysis by uv spectroscopy after extraction by liquid-liquid partition.
Oral Acute oral LD50 of ryania for rats 1200, mice 650 mg/kg. Lethal dose of ryanodine in
dogs 0.4 mg/kg. NOEL In 150 d feeding trials, guinea-pigs and chickens receiving
10 g/kg diet suffered no toxic symptom. Toxicity Class WHO (a.i.) III EPA (formulation)
III ECClassification Xn; R21/22| N; R50, R53
ECOTOXICOLOGY:
Fish Toxic to fish.
salicylanilide
Fungicide
NOMENCLATURE:
Common name salicylanilide (BSI, E-ISO, F-ISO, JMAF, accepted in lieu of a common
name.)
IUPACname salicylanilide
Chemical Abstracts name 2-hydroxy-N-phenylbenzamide CASRN[87172]
SmilescodeOc1ccccc1C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 213.2 M.f. C13H11NO2
salicylanilide 475
COMMERCIALISATION:
History Fungicide reported by R. G. Fargher etal. (Mem. Shirley Inst., 1930, 9, 37).
Introduced by ICI Limited.
APPLICATIONS:
PRODUCTS:
Discontinued products Shirlan* (ICI).
schradan
IRAC1B
NOMENCLATURE:
Common name schradan (BSI, E-ISO, ESA, JMAF); schradane ((m) F-ISO)
IUPACname octamethylpyrophosphoric tetra-amide
Chemical Abstracts name octamethyldiphosphoramide Other names OMPA
CASRN[152169] ECno2058010
SmilescodeCN(C)P(=O)(OP(=O)(N(C)C)N(C)C)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. contains decamethyltriphosphoric triamide, ((CH3)2N)2PO.OPO.
(N(CH3)2)OPO(N(CH3)2)2, (2550%), which is also insecticidal, and other amides of
higher phosphoric acids. Mol. wt. 286.3 M.f. C8H24N4O3P2 Form Colourless, viscous
liquid. M.p.1420C B.p. 118122C /0.3 mmHg V.p.c.100 mPa (25C)
S.g./density 1.1343 (25C) Solubility Miscible with water and most organic solvents;
slightly soluble in petroleum oils. Stability Stable to water and alkali, but hydrolysed under
acid conditions to dimethylamine and orthophosphoric acid.
COMMERCIALISATION:
History Systemic insecticide discovered by G. Schrader & H. Kenthal (cited by G.
Schrader, Phosphorsure-Ester, p. 88). Introduced by Pest Control Ltd (later Schering
Agriculture). Patents GB 631549, GB 652981.
APPLICATIONS:
acaricide. Relatively inert as a contact insecticide. Uses Effective against sap-feeding insects
and mites. Used as a soil drench for transplanted trees.
PRODUCTS:
Discontinued products Pestox3* (FBC); PestoxIII* (FBC);
Discontinuedmixtures Sytam* (+dimefox) (with tris(dimethylamino)phosphine oxide)
476 schradan
(Murphy, Wacker); Terra Sytam* (+dimefox) (with tris(dimethylamino)phosphine oxide)

(Murphy, Wacker).
ANALYSIS:
Product analysis CIPACHandbook, 1983, 1B, 1795; mixture with dimefox, 1980, 1A, 334.
Oral Acute oral LD50 for male rats 9.1, female rats 42 mg/kg. Toxicity Class WHO (a.i.) Ia
scilliroside
Rodenticide
O
CH3
H
CH3 OH
CH2OH H OH
OO
OH OCOCH3
OH
NOMENCLATURE: OH
Common name scilliroside (JMAF)
IUPACname 3-(-D-glucopyranosyloxy)-17-(2-oxo-2H-pyran-5-yl)-14-androst-4-
ene-6,8,14-triol 6-acetate
Chemical Abstracts name (3,6)-6-acetyloxy-3-(-D-glucopyranosyloxy)-8,14-
dihydroxybufa-4,20,22-trienolide Other names red squill CASRN[507608]
ECno2080774 SmilescodeCC(=O)OC1CC2(O)C(CCC3(C)C(CCC32O)
c4ccc(=O)oc4)C5(C)CC(CC=C15)OC6OC(CO)C(O)C(O)C6O
PHYSICAL CHEMISTRY:
Composition The name scilliroside applies to a glycoside contained in the extract of the
powdered bulbs of the red squill, Urginea (Scilla) maritima. Mol. wt. 620.7
M.f. C32H44O12 Form Hydrated prisms (from aqueous methanol) which losec.8% m/m in
vacuo, giving a hemihydrate. M.p.168170C (hemihydrate) V.p. Very low
Solubility Slightly soluble in water. Readily soluble in alcohols, ethylene glycol, dioxane
and glacial acetic acid. Slightly soluble in ethyl acetate, acetone and chloroform. Practically
insoluble in diethyl ether and petroleum ether. Stability Decomposes at 200C; bulbs
should be dried at temperatures below 80C. Dried red squill powder loses its scilliroside
scilliroside 477
content on storage and when exposed to the atmosphere. Specific rotation []D20 59
to 60 (methanol)
COMMERCIALISATION:
History Rodenticide. Red squill has been used since the 13th century. Scilliroside, the
toxic principle, was isolated and identified by A. Stoll & J. Renz (Helv. Chim. Acta, 1942, 25,
377; 1943, 26, 648). Chemistry and toxicology of cardiac glycosides reviewed by A. Stoll
(Experientia, 1954, 10, 282). The two varieties of U. maritima, red squill and white squill,
contain glycosides, but only the former was used against rats.
APPLICATIONS:
Biochemistry Activity may be due to metabolism to the aglycone, scillirosidin. Causes
emesis, and affects the cardiovascular and central nervous systems. Its specific toxicity to
rats may be due to the inability of the rodent to vomit, a reaction squill induces in other
animals. ModeofactionSelective rodenticide with stomach action. Uses Control of
most species of rodents, e.g. brown rats (Rattus norvegicus), black rats (Rattus rattus), house
mice (Mus musculus), long-tailed field mice (Apodemus sylvaticus), and Field voles (Microtus
agrestis). Formulation types RB; GB.
ANALYSIS:
Product analysis by tlc, or by chromatographic separation on paper and, after elution,
photometric assay (M. Wichtl & L. Fuchs, Arch. Pharm., 1962, 295, 361).
Oral Acute oral LD50 for male rats 0.7, female rats 0.43 mg/kg (A. Stoll & J. Renz Helv. Chim.
Acta, 1942, 25, 377; 1943, 26, 648). Dogs, cats, and pigs survived 16 mg/kg (S. A. Barnett et
al., J. Hyg. 1949, 47, 431). In most mammals, with the exception of rodents, scilliroside is an
emetic. Toxicity Class WHO (a.i.) Ia EPA (formulation) I ECClassification T+; R28
ECOTOXICOLOGY:
Birds Fowls survived 400 mg/kg.
sebuthylazine
Herbicide
Cl
N
NH N
N
NH
NOMENCLATURE:
2-sec-butylamino-4-chloro-6-ethylamino-1,3,5-triazine
Common name sebuthylazine (BSI, E-ISO, (f) F-ISO)
478 sebuthylazine
IUPACname N2-sec-butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine; 2-sec-

butylamino-4-chloro-6-ethylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N-ethyl-N-(1-methylpropyl)-1,3,5-
triazine-2,4-diamine CASRN[7286693] DevelopmentcodesGS 13 528
SmilescodeCCCCNc1nc(Cl)nc(NCC)n1
PHYSICAL CHEMISTRY:
Mol. wt. 229.7 M.f. C9H16ClN5 Form Colourless powder. M.p.159161C
Solubility Sparingly soluble in water. Soluble in acetone, benzene, dioxane; very soluble in
chloroform; slightly soluble in diethyl ether, ethanol.
COMMERCIALISATION:
History Herbicide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinuedmixtures Vorox(i)Granulat 371* (+amitrole +atrazine) (Spiess).
secbumeton
Herbicide
NOMENCLATURE:
Common name secbumeton (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname N2-sec-butyl-N4-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylpropyl)-1,3,5-triazine-2,4-
diamine CASRN[26259450] ECno2475541 DevelopmentcodesGS 14 254
(Geigy) SmilescodeCCNc1nc(NC(C)CC)nc(OC)n1
M.p.8688C V.p. 0.97 mPa (20C) Henry 3.64 104 Pa m3 mol1 (calc.)
dichloromethane 600, hexane 22, methanol 500, n-octanol 200, toluene 350 (all in g/l,
20C). Stability DT50 (calc.) 30 d (pH 1), 175 d (pH 13) (20C). pKa 4.4
COMMERCIALISATION:
History Herbicide reported by A. Gast & E. Fankhauser (Proc. Br.Weed Control Conf., 8th,
1966, p. 485). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 337019; GB
814948
APPLICATIONS:
ModeofactionTotal and selective herbicide, taken up by leaves and roots.
Uses Controls mono- and di-cotyledonous weeds both annual and perennial. It was used
in established lucerne either at 13 kg/ha or in combination with simazine. In combination
with terbuthylazine it was suitable for non-cropped land. Formulation types WP.
secbumeton 479
PRODUCTS:
Discontinued products Etazine* (Ciba-Geigy); Etazine 3585* (Ciba-Geigy); Sumitol*
(Ciba-Geigy); Discontinuedmixtures Etazine 3947* (+simazine) (Ciba-Geigy);
Primatol 3588* (+terbuthylazine) (Ciba-Geigy).
ANALYSIS:
Product analysis by glc or by acidimetric titration. Residues determined by glc with MCD
or FPD (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192; E. Knsli, Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 13).
Oral Acute oral LD50 for rats 2680 mg tech./kg. NOEL (90 d) for rats 640 mg/kg diet (c
43 mg/kg daily), for dogs 1600 mg/kg diet (40 mg/kg daily). Toxicity Class WHO (a.i.) U
ECClassification Xn; R22| Xi; R36| N; R50, R53
sesamex
NOMENCLATURE:
Common name sesamex (ESA)
IUPACname 5-[1-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-1,3-benzodioxole (I);
2-(1,3-benzodioxol-5-yloxy)-3,6,9-trioxaundecane
SmilescodeCCOCCOCCOC(C)Oc1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
Mol. wt. 298.3 M.f. C15H22O6 Form Straw-coloured liquid with a faint odour.
B.p. 137141C /0.08 mmHg Solubility Readily soluble in kerosine and
dichlorodifluoromethane. Stability Unstable in sunlight and on powdered carriers.
COMMERCIALISATION:
History Synergist for pyrethroid insecticides reported by M. Beroza (J. Agric. Food Chem.,
1956, 4, 49). Introduced by Shulton Inc.
PRODUCTS:
Discontinued products Sesoxane* (Shulton).
Oral Acute oral LD50 for rats 20002270 mg/kg. Toxicity Class WHO (a.i.) III
480 sesamex
sesasmolin
NOMENCLATURE:
Common name sesasmolin (ESA)
IUPACname 1,3-benzodioxol-5-yl (1R,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)
perhydrofuro[3,4-c]furan-1-yl ether; 1-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-yloxy)
tetrahydrofuro[3,4-c]furan; 2-(1,3-benzodioxol-5-yl)-6-(1,3-benzodioxol-5-yloxy)-3,7-
dioxabicyclo[3.3.0]octane
Chemical Abstracts name [1S-(1,3a,4,6a)]-5-[4-(1,3-benzodioxol-5-yloxy)
tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole CASRN[526078]
SmilescodeC1Oc2ccc(OC3OCC4C(OCC34)c5ccc6OCOc6c5)cc2O1
PHYSICAL CHEMISTRY:
Mol. wt. 370.4 M.f. C20H18O7
COMMERCIALISATION:
History Synergistic activity with pyrethrum of sesame oil (from Sesamum indicum)
reported by C. Eagleson (Soap Chem. Spec., 1942, 18(12), 125) and traced to sesasmolin by
H. L. Haller etal. (J. Org. Chem., 1942, 7, 183; J. Econ. Entomol., 1942, 35, 247).
simeton
Herbicide
NOMENCLATURE:
Common name simeton (BSI, WSSA)
IUPACname N2,N4-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine; 2,4-bis(ethylamino)-6-
methoxy-1,3,5-triazine
Chemical Abstracts name N,N-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine
SmilescodeCCNc1nc(NCC)nc(OC)n1
PHYSICAL CHEMISTRY:
Mol. wt. 197.2 M.f. C8H15N5O
COMMERCIALISATION:
History Herbicide developed by J. R. Geigy S.A. (later Ciba-Geigy AG).
simeton 481
SMY 1500
Herbicide
N N
(CH3)3C SCH2CH3
N
O NH2
NOMENCLATURE:
IUPACname 4-amino-6-tert-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one
Chemical Abstracts name 4-amino-6-(1,1-dimethylethyl)-3-(ethylthio)-
1,2,4-triazin-5(4H)-one Other names ethiozin * (rejected common name
proposal) CASRN[64529562] DevelopmentcodesSMY 1500 (Bayer)
SmilescodeCCSc1nnc(c(=O)n1N)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 228.3 M.f. C9H16N4OS Form Colourless crystals. M.p.96.4C
V.p. 7.5 103 mPa (20C) Kow logP = 2.08 Henry 5.04 103 Pa m3 mol1 (calc.)
Solubility In water 0.34 mg/l (20C). In dichloromethane >200, isopropanol 100200,
toluene 100200 g/kg.
COMMERCIALISATION:
History Herbicide reported by H. Hack & L. Eue (Proc. 1985 Br. Crop Prot. Conf. - Weeds,
1, 35). Introduced in Israel (1989) by Bayer AG.
APPLICATIONS:
site. Uses Pre-emergence control of grasses (particularly Bromus spp.) and some broad-
leaved weeds in cereals (mainly wheat) and tomatoes at 0.551.7 kg/ha.
Formulation types WG .
PRODUCTS:
Discontinued products Lektan* (Bayer); Tycor* (Bayer).
Oral Acute oral LD50 for ratsc.2000 mg/kg, micec.1000, dogs >5000 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. NOEL (2 y) for rats 25
mg/kg diet. ADI/RfD (EPA) 0.05 mg/kg b.w. [1990].
482 SMY 1500

SN 106 279
Herbicide
O O CO2CH3
CH
F3C Cl CH3
NOMENCLATURE:
IUPACname methyl (R)-2-(7-(2-chloro-,,-trifluoro-p-tolyloxy)-2-naphthyloxy)
propionate
Chemical Abstracts name methyl (R)-2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-
naphthalenyl]oxy]propanoate CASRN[103055614]
DevelopmentcodesSN 106 279
PHYSICAL CHEMISTRY:
Mol. wt. 424.8 M.f. C21H16ClF3O4 Form Tech. is a yellow liquid. V.p. 2.39 103 mPa
(25C) Solubility In water 0.7 mg/l. In ethanol and acetone 870, methanol 850 (g/l,
20C).
COMMERCIALISATION:
History Herbicide evaluated by Schering AG. Reported by F. Arndt etal. (Proc. Br. Crop Prot.
Conf. Weeds, 1989, 1, 35).
APPLICATIONS:
ModeofactionTaken up principally by plant leaves. Treated plants display diphenyl ether
symptoms of root and shoot necrosis of meristems. Uses Post-emergence herbicide for
control of broad-leaved weeds, such as Veronica spp., Viola spp., Lamium spp., in winter
cereals, at 100200 g/ha.
Oral Acute oral LD50 for male rats >400 mg/kg. Skin and eye Acute percutaneous LD50
for male rats >>400 mg/kg.
SN 106 279 483

SN 72129
Insecticide
O
NH
S C Cl
N
NOMENCLATURE:
IUPACname (E)-2-chlorobenzoyl(2,3-dihydro-4-phenyl-1,3-thiazol-2-ylidene)acetonitrile
Chemical Abstracts name (E)-2-chloro--oxo--(4-phenyl-2(3H)-thiazolylidene)
benzenepropanenitrile Other names thiapronil* (unadopted proposed common name)
CASRN[77768582] unstated stereochemistry DevelopmentcodesSN 72129
SmilescodeClc1ccccc1C(=O)C(=C2NC(=CS2)c3ccccc3)C#N
PHYSICAL CHEMISTRY:
Mol. wt. 338.8 M.f. C18H11ClN2OS Form Colourless crystals. M.p.182183C
V.p. <1.3 105 mPa (25C) Solubility In water 69 mg/l (room temperature). In acetone
0.015, methanol 4.2, isopropanol 1.9 (all in g/l). Stability Stable in acid and alkali.
COMMERCIALISATION:
History Insecticide reported by H. Joppien etal. (Proc. 10th Int. Congr. Plant Prot., 1983, 1,
rabbits >2000 mg/kg.
sodium (Z)-3-chloroacrylate
NOMENCLATURE:
IUPACname sodium (Z)-3-chloroacrylate
Chemical Abstracts name sodium (Z)-3-chloro-2-propenoate
Other names sodium cis-3-chloroacrylate CASRN[4312974]
DevelopmentcodesUC 20 299 Smilescode[Na+].[O-]C(=O)/C=C\Cl; without
stereochemistry:[Na+].[O-]C(=O)C=CCl
PHYSICAL CHEMISTRY:
Mol. wt. 128.5 M.f. C3H2ClNaO2
COMMERCIALISATION:
History Herbicide reported by R. A. Herrett & A. N. Kurtz (Science, 1963, 141, 1192).
Introduced as a defoliant by Union Carbide Corp. (later Rhne-Poulenc Ag.).
484
sodium (Z)-3-chloroacrylate
PRODUCTS:
Discontinued products Prep* (Union Carbide).
ECClassification Xn; R21/22
sodium fluoride
Insecticide
NaF
NOMENCLATURE:
Common name fluorure de sodium (F-ISO, used in lieu of a common name); sodium
fluoride (E-ISO, used in lieu of a common name)
IUPACname sodium fluoride
Chemical Abstracts name sodium fluoride CASRN[7681494] ECno2316678
Smilescode[F-].[Na+]
PHYSICAL CHEMISTRY:
Mol. wt. 42.0 M.f. FNa Form Colourless powder. M.p.993C V.p. Negligible (room
temperature) S.g./density 2.8 Solubility In water 42.2 g/l (18C). Slightly soluble in
ethanol.
COMMERCIALISATION:
History Introduced in baits against insects in stores.
APPLICATIONS:
ModeofactionInsecticide with stomach and contact action. Uses Used in insect baits
and as a timber preservative. Phytotoxicity Highly phytotoxic.
PRODUCTS:
Discontinued products Florocid* (Allied).
ANALYSIS:
Product analysis is by determination of the fluorine content by titrimetric methods
(AOACMethods, 18th Ed., 921.04, 929.04, 933.03).
ICSC.951 (2003).
Oral Highly toxic, the lowest oral lethal dose being 28100 mg/kg for a range of
vertebrates. Acute oral LD50 for rats 180 mg/kg (Am. Ind. Hyg. Assoc. J., 1969, 30, 470).
Toxicity Class WHO (a.i.) II ECClassification T; R25| Xi; R36/38| R32
sodium fluoride 485

sodium fluoroacetate
Rodenticide
FCH2C
O 2N
a
IRAC26
NOMENCLATURE:
Common name sodium fluoroacetate (E-ISO, accepted in lieu of a common name);
fluoroac(tate de sodium) (F-ISO, accepted in lieu of a common name); fluoroacetic acid
(BSI, for parent acid)
IUPACname sodium fluoroacetate
Chemical Abstracts name sodium fluoroacetate Other names Compound 1080
CASRN[62748] ECno2005482 Smilescode[Na+].[O-]C(=O)CF
PHYSICAL CHEMISTRY:
Mol. wt. 100.0 M.f. C2H2FNaO2 Form Colourless, hygroscopic powder.
M.p.Decomposesc.200C V.p. Non-volatile Solubility Very soluble in water. Almost
insoluble in ethanol, acetone and petroleum oils.
COMMERCIALISATION:
History Rodenticidal properties reported by E. R. Kalmbeck (Science, 1945, 102, 232).
APPLICATIONS:
Biochemistry Inhibits aconitase in the tricarboxylic acid cycle. Uses Used in baits for
control of rodents. In Australia, also used for control of wild rabbits, wild dogs and wild
pigs. Formulation types CB .
ANALYSIS:
Product analysis is by conversion to lead chloride fluoride (AOACMethods, 14th Ed.,
6.0196.062); sodium fluoride is a usual contaminant. For a qualitative determination
of fluoroacetic acid in residues, see AOACMethods, 18th Ed., 949.09; for quantitive
determination by extraction, see ibid., 949.10, followed by fluorine determination, ibid.,
944.08.
PDS 16 (1975). ICSC.484 (1997).
Oral Acute oral LD50 for Rattus norvegicus 0.22 mg/kg (S. H. Dieke & C. P. Richter, U.S.
Public Health Rep., 1946, 61, 672). Highly toxic to all other mammals (see Sodium
monofluoroacetate). NOEL NOAEL (13 w) for rats 0.05 mg/kg b.w. daily (EPA RED).
ADI/RfD (EPA) cRfD 0.00002 mg/kg b.w. [1993, 1995]. Toxicity Class WHO (a.i.) Ia.
ECClassification T+; R26/27/28| N; R50
486 sodium fluoroacetate

sodium selenate
Insecticide
NOMENCLATURE:
IUPACname sodium selenate
Chemical Abstracts name disodium selenate CASRN[13410010]
Smilescode[Na+].[Na+].[O-][Se](=O)(=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 188.9 M.f. Na2O4Se
COMMERCIALISATION:
History Introduced as an insecticide.
sophamide
Insecticide
IRAC1B
NOMENCLATURE:
Common name sophamide (BSI, E-ISO, (m) F-ISO)
IUPACname S-methoxymethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-methoxymethylacetamide
Chemical Abstracts name S-[2-[(methoxymethyl)amino]-2-oxoethyl] O,O-
dimethyl phosphorodithioate CASRN[37032158] DevelopmentcodesMC-62
SmilescodeCOCNC(=O)CSP(=S)(OC)OC
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Insecticide evaluated by Murphy Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Formocarbam* (Murphy).
sophamide 487
SSF-109
Fungicide
N N
HO N N HO N N
Cl H Cl H
(1S,2S)- isomer (1R,2R)- isomer

NOMENCLATURE:
Chemical Abstracts name ()-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)
cycloheptanol CASRN[129586329] DevelopmentcodesSSF-109 (Shionogi)
SmilescodeOC1(CCCCCC1n2cncn2)c3ccc(Cl)cc3
PHYSICAL CHEMISTRY:
Mol. wt. 291.8 M.f. C15H18ClN3O Form Colourless crystals. M.p.128129C
Kow logP = 0.481 Solubility In water 125 mg/l (25C).
COMMERCIALISATION:
History Broad-spectrum fungicide introduced by Shionogi and Co. Ltd (whose
agrochemical interests became Aventis CropScience Shionogi K.K. in 2001, became part of
Bayer AG).
APPLICATIONS:
Biochemistry Inhibits ergosterol biosynthesis. ModeofactionSystemic fungicide with
preventive and curative action. Uses Broad-spectrum fungicide for control of Ascomycetes,
Phycomycetes, Basidiomycetes, and Fungi Imperfecti on lettuce, cucumbers, wheat, oats,
and rice. Particularly active against grey mould (Botrytis cinerea), including benzimidazole-
resistant strains.
ANALYSIS:
Product by tlc or hplc.
Oral Acute oral LD50 for rats 153214, mice 273 mg/kg. Other Negative in the Ames test
and micronucleus test.
ECOTOXICOLOGY:
Fish LC50 (48 h) for carp 22.5, killifish 10.9 mg/l. Daphnia LC50 (3 h) for Daphnia pulex
100.5 mg/l.
488 SSF-109
SSH-108
(CH3)2CHNH N NHCH(CH3)2
N N
SCHF2
NOMENCLATURE:
IUPACname 2-difluoromethylthio-4,6-bis(isopropylamino)-1,3,5-triazine
Chemical Abstracts name 6-[(difluoromethyl)thio]-N,N-bis(1-methylethyl)-1,3,5-
triazine-2,4-diamine CASRN[103427732] DevelopmentcodesSSH-108
PHYSICAL CHEMISTRY:
Mol. wt. 277.3 M.f. C10H17F2N5S
APPLICATIONS: Uses In mixture with acetochlor for use in maize and other crops.
SSI-121
Acaricide
CH2Si(CH3)3
CH2 Sn CH2
(CH3)2C C(CH3)2
Cl
NOMENCLATURE:
IUPACname ((chlorobis(2-methyl-2-phenylpropyl)stannyl)methyl)trimethylsilane
Chemical Abstracts name [[chlorobis(2-methyl-2-phenylpropyl)stannyl]methyl]
trimethylsilane Other names bis(2-methyl-2-phenylpropyl)trimethylsilylmethyl stannyl
chloride(II) CASRN[108307079] DevelopmentcodesSSI-121 (Shionogi)
SmilescodeCC(C)(c1ccccc1)[Sn](Cl)(C[Si](C)(C)C)C(C)(C)c2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 507.8 M.f. C24H37ClSiSn
COMMERCIALISATION:
History Acaricide evaluated by Shionogi and Co., Ltd; discontinued in 1994.
APPLICATIONS:
ModeofactionContact acaricide. Uses Control of all stages of spider mites (including
cyhexatin- and fenbutatin oxide-resistant strains) on apples, citrus fruit, tea, and other
crops. Formulation types WP.
EHC 15 (1980) is a general review of tin and tin compounds.
SSI-121 489
Oral Acute oral LD50 for rats 2000 mg/kg (Shibuya). Skin and eye Acute percutaneous
LD50 for rats >1000 mg/kg (Shibuya).
strychnine
Rodenticide
HO
O
H
N
H
H H
N
NOMENCLATURE:
Common name strychnine (BSI, E-ISO, F-ISO, accepted in lieu of a common name)
IUPACname strychnidin-10-one
Chemical Abstracts name strychnidin-10-one CASRN[57249] ECno2003197
SmilescodeO=C1C[C@@H]2OCC=C3CN4CC[C@]56[C@@H]4C[C@@H]3[C@
@H]2[C@@H]6N1c7ccccc75;without stereochemistry:O=C1CC2OCC=C3CN4CCC56
C4CC3C2C6N1c7ccccc75
PHYSICAL CHEMISTRY:
Mol. wt. 334.4 M.f. C21H22N2O2 Form Colourless crystals. M.p.270280C (decomp.);
>199C (sulfate) Kow logP = 4.0 (pH 7) Solubility In water 143 mg/l. In benzene 5.6,
ethanol 6.7, chloroform 200 (all in g/l). Sparingly soluble in diethyl ether and petroleum
spirit. Sulfate solubility in water 30 g/l (15C); soluble in ethanol. Stability Stable to
light, and at pH 59. Strychnine is a base, and forms water-soluble salts with acids: the
hydrochloride, with 1.52.0 moles of water of crystallisation which are lost at 110C; the
sulfate, as pentahydrate, becoming anhydrous at 100C. Specific rotation []D18 139
(chloroform) pKa 8.26
COMMERCIALISATION:
Production Produced by extracting seeds of Strychnos or Loganiaceae spp. History The
physiological properties of the alkaloids in extracts of Strychnos (Loganiaceae) species
have long been known, strychnine being the most important. Seeds of Strychnos nux-
vomica were used as a rat poison in Germany in the late 17th century. Strychnine was
first isolated in pure form from St. Ignatius beans (Strychnos ignatii) in 1818 (Pest Control
Agents from Natural Products).
APPLICATIONS:
Biochemistry Antagonist to the neurotransmitter glycine, acting principally on the
spinal cord. ModeofactionRodenticide absorbed mainly by the intestine. Uses Used
490 strychnine
(as strychnine sulfate) for control of moles, squirrels, rabbits, gophers, mice and other
small mammals, and also for control of sparrows, pigeons and other bird pests. Rats are
somewhat resistant, as they normally avoid the bait. Formulation types CB; RB .
ANALYSIS:
Product analysis by acid-base titration (AOACMethods, 18th Ed., 920.211) or by
spectrophotometry (ibid., 962.22).
ICSC.197 (2000). EU Status (1107/2009) Not approved, 2004/129/EC.
Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. ADI/RfD (EPA) cRfD
0.0003 mg/kg b.w. [1988]. Other Lethal dose: for rats 130 mg/kg; for bearsc.0.5 mg/kg;
for man 3060 mg/kg. Toxicity Class WHO (a.i.) Ib. ECClassification T+; R27/28| N;
R50, R53 (base): T+; R26/28| N; R50, R53 (salts)
ECOTOXICOLOGY:
Birds Acute oral LD50 for starlings <5.0 mg sulfate/kg. Dietary LC50 for bobwhite
quailc.4000, mallard ducksc.200 ppm.
ENVIRONMENTAL FATE:
Animals Rapidly absorbed by gastro-intestinal tract but not through the skin. Distribution,
metabolism to several non-toxic polar products, and excretion, are rapid. Only 520% of
unchanged alkaloid is excreted in the urine; the major metabolites were the 21,22-epoxide
and strychnine N-oxide. Soil/Environment Immobile in soil; degraded microbially.
sulfallate
Herbicide
NOMENCLATURE:
Common name CDEC (WSSA); sulfallate (BSI, E-ISO, (m) F-ISO)
IUPACname 2-chloroallyl diethyldithiocarbamate
Chemical Abstracts name 2-chloro-2-propenyl diethylcarbamodithioate
CASRN[95067] ECno2023889 DevelopmentcodesCP 4742 (Monsanto)
SmilescodeCCN(CC)C(=S)SCC(=C)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 223.8 M.f. C8H14ClNS2 Form Amber oil.
B.p. 128C /1 mmHg V.p. 293 mPa (20C) S.g./density 1.088 (25C) Solubility In
water 92 mg/l (25C). Soluble in most organic solvents. Stability Hydrolysed by alkali;
DT50 47 d (pH 5), 30 d (pH 8).
COMMERCIALISATION:
History Herbicide introduced by the Monsanto Co. Patents US 2744898, US 2919182.
sulfallate 491
APPLICATIONS:
Biochemistry Inhibits lipid metabolism. ModeofactionSystemic, selective herbicide,
readily absorbed by plant roots but not by foliage. Uses As a pre-em. herbicide
(36 kg/ha) on a wide range of vegetable crops controlling annual weeds, but not
established or vegetatively propagating perennials. Formulation types EC; GR .
PRODUCTS:
Discontinued products Vegadex* (Monsanto).
ANALYSIS:
Product analysis is by glc. Residues may be determined by glc (Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 704; see also Pestic. Anal. Man., I, 302).
IARC 30 (1983).
IARC Class 2B
Oral Acute oral LD50 for rats 850 mg/kg. Skin and eye It is somewhat irritant to skin and
eyes. Toxicity Class WHO (a.i.) II ECClassification R45| Xn; R22| N; R50, R53
ENVIRONMENTAL FATE:
Soil/Environment Persists in soil for 2142 d.
sulfoxide
NOMENCLATURE:
Common name sulfoxide (ESA)
IUPACname 2-(1,3-benzodioxol-5-yl)-1-methylethyl octyl sulfoxide; 1-methyl-2-(3,4-
methylenedioxyphenyl)ethyl octyl sulfoxide
Chemical Abstracts name 5-[2-(octylsulfinyl)propyl]-1,3-benzodioxole
CASRN[120627] SmilescodeCCCCCCCCS(=O)C(C)Cc1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
Composition Tech. is 88%. Mol. wt. 324.5 M.f. C18H28O3S Form Tech. is a brown liquid
with a mild odour. B.p. Decomposes without boiling. S.g./density 1.061.09 (25C, tech.)
Solubility Practically insoluble in water. Miscible with most organic solvents; in petroleum
oils 2025 g/kg.
COMMERCIALISATION:
History Synergist for pyrethroid insecticides reported by M. E. Synerholm etal. (Contrib.
Boyce Thompson Inst., 1947, 15, 35). Introduced by S. B. Penick & Co. Patents US 2486445
(to Boyce Thompson Institute).
PRODUCTS:
Discontinued products Sulfocide* (Penick).
492 sulfoxide
ANALYSIS:
Product analysis is by uv spectroscopy at 288 nm, after isolation by steam distilllation
(WHO Insecticides, 30 Rev. 1,p. 170).
Oral Acute oral LD50 for rats 20002500 mg/kg. Toxicity Class WHO (a.i.) III
sulglycapin
Herbicide
NOMENCLATURE:
Common name sulglycapin (BSI, E-ISO, (m) F-ISO)
IUPACname azepan-1-ylcarbonylmethyl methylsulfamate
Chemical Abstracts name 2-(hexahydro-1H-azepin-1-yl)-2-oxoethyl methylsulfamate
CASRN[51068601] DevelopmentcodesBAS 461H; BAS 46 100H (both BASF)
SmilescodeCNS(=O)(=O)OCC(=O)N1CCCCCC1
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C9H18N2O4S
COMMERCIALISATION:
History Herbicide reported by E. Eysell etal. (Proc. Br. Crop Prot. Conf. Weeds, 1976, 2,
709). Evaluated by BASF AG.
sulprofos
Insecticide
S OCH2CH3
P
CH3S O SCH2CH2CH3
IRAC1B
NOMENCLATURE:
Common name sulprofos (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate
Chemical Abstracts name O-ethyl O-[4-(methylthio)phenyl] S-propyl
phosphorodithioate CASRN[35400432] DevelopmentcodesNTN 9306;
BAY 123234 (both Bayer) SmilescodeCCCSP(=S)(OCC)Oc1ccc(SC)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 322.4 M.f. C12H19O2PS3 Form Colourless oil, with a mercaptan-like odour; (tech.,
tan liquid). M.p.15C (tech.) B.p. 125C /1 Pa V.p. 0.084 mPa (20C); 0.16 mPa (25C)
sulprofos 493
Kow logP = 5.48 Henry 8.74 10-2 Pa m3 mol1 (20C, calc.) S.g./density 1.20 (20C)
Solubility In water 0.31 mg/l (20C). In isopropanol 400600, dichloromethane, hexane,
toluene >1200 (all in g/l, 20C). Stability Hydrolysis in buffer systems, DT50 (22C) 26 d
(pH 4), 151 d (pH 7), 51 d (pH 9). Photodegraded in water and on soil surfaces. For films in
sunlight, 50% decomposition occurs in <2 days. F.p. 64C
COMMERCIALISATION:
History Insecticide reported by G. Zoebelein (Proc. Conf. Pest Control, 4th, Cairo, 1978,
p. 456). Introduced by Bayer AG. Patents NL 6508899 (1965) (to Bayer)
Manufacturers Bayer Corp.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic insecticide with
contact and stomach action. Uses Control of Lepidoptera, Thysanoptera, Heliothis spp., and
other insects in cotton, soya beans, tobacco, vegetables, and tomatoes.
Formulation types EC; UL .
PRODUCTS:
Discontinued products Bolstar* (Bayer CropScience); Helothion* (Bayer).
ANALYSIS:
Product analysis by glc with FID (AOACMethods, 18th Ed., 980.12).
EHC 63 (1986; a general review of organophosphorus insecticides). ICSC.248 (1995).
Oral Acute oral LD50 for male rats 304, female rats 176, male and female micec.1700 mg/
kg. Skin and eye Acute percutaneous LD50 for male rats 5491, female rats 1064 mg/kg.
Not irritating to skin; mild irritant to eyes (rabbits). Not a skin sensitiser. Inhalation LC50
(4 h) for male and female rats >4130 g/l air. NOEL (2 y) for dogs 10 mg/kg diet (0.25 mg/
kg b.w.), rats 6, mice 2.5. ADI/RfD (EPA) 0.003 mg/kg b.w. [1986]. Toxicity Class WHO
(a.i.) II EPA (formulation) II ECClassification (T; R25| Xn; R21)
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 47 mg/kg. Dietary LC50 (5 d) for bobwhite
quail 99 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 1114, rainbow trout 2338 mg/l.
Daphnia LC50 (48 h) 0.831 g/l. Algae ErC50 for Selenastrum capricornutum 64 mg/l.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration,c.92% is eliminated within 24 h. The main
degradation products are the oxygen-analogue, phenol, sulprofos sulfoxide and sulprofos
sulfone, and the corresponding oxygen-analogues and phenols. Plants The major
metabolites are sulprofos sulfoxide and sulprofos sulfone. The corresponding phenols and
oxygen-analogues are minor degradation products. Soil/Environment The adsorption
of sulprofos in various soil types occurred rapidly; the compound is highly adsorbed.
DT50 in the range of some days to several weeks, depending on the soil types. The major
metabolites are sulprofos sulfoxide and sulprofos sulfone.
494 sulprofos
sultropen
Fungicide
NOMENCLATURE:
Common name sultrop(ne) ((m) F-ISO); sultropen (BSI, E-ISO)
IUPACname 2,4-dinitrophenyl pentyl sulfone
Chemical Abstracts name 2,4-dinitro-1-(pentylsulfonyl)benzene
CASRN[963224] DevelopmentcodesRD 7901; BTS 7901
SmilescodeCCCCCS(=O)(=O)c1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 302.3 M.f. C11H14N2O6S
COMMERCIALISATION:
History Fungicide evaluated by Boots Co., Ltd (later Schering Agrochemicals).
swep
Herbicide
NOMENCLATURE:
Common name swep (ANSI, WSSA); MCC (JMAF)
IUPACname methyl 3,4-dichlorocarbanilate
Chemical Abstracts name methyl (3,4-dichlorophenyl)carbamate
SmilescodeCOC(=O)Nc1ccc(Cl)c(Cl)c1
PHYSICAL CHEMISTRY:
Mol. wt. 220.1 M.f. C8H7Cl2NO2
COMMERCIALISATION:
History Herbicide reported by H. R. Hudgins (Proc. South. Weed Control Conf., 1963, 16,
118). Introduced by FMC Corp.
ANALYSIS:
In water, by lc with uv detection, see AOACMethods, 18th Ed., 992.14.
swep 495
SYP-Z048
Fungicide
CH3
N O
CH3 Cl
N
NOMENCLATURE:
Chemical Abstracts name 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine
Other names dingjunezuo CASRN[847749375] DevelopmentcodesSYP-Z048
(Shenyang Research)
PHYSICAL CHEMISTRY:
Mol. wt. 288.8 M.f. C16H17ClN2O Form Light yellow sticky oil. Solubility Insoluble in
water.Very soluble in acetone, ethyl acetate and chloroform.
COMMERCIALISATION:
History Discovered by Shenyang Research Institute of Chemical Industry in 1996 and
registered in China in 2002.
APPLICATIONS:
ModeofactionBroad spectrum systemic fungicide with protective and curative
properties. Uses For control of tomato grey mould, apple spot leaf drop, peanut brown
spot, cucumber scab, wheat root rot and grape white rot. Formulation types EC.
PRODUCTS:
Other products Jun Si Qi (Shenyang Research).
dermal LD50 for rabbits >2000 mg/kg. Other Negative in Ames test.
496 SYP-Z048
SYP-Z071
Fungicide
CH3
O
N
O O
Cl CH3
O
CH3
FRAC11, C3; QoI; strobilurin type: methoxyacrylate
NOMENCLATURE:
IUPACname methyl 2-{2-[3-(4-chlorophenyl)-1-methylallylideneaminooxymethyl]
phenyl}-3-methoxyacrylate
Other names enestroburin; enestrobin CASRN[750643573]
DevelopmentcodesSYP-Z071
SmilescodeCOC=C(C(=O)OC)c1ccccc1CON=C(C)C=Cc2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 399.9 M.f. C22H22ClNO4 Form White crystals; (tech. is a pale yellow oil).
Solubility Insoluble in water.Very soluble in acetone, ether and chloroform.
COMMERCIALISATION:
History Discovered by Shenyang Research Institute of Chemical Industry in 1997 and
reported by L. X. Zhang etal. (Proc. BCPC. Int. Congr., Glasgow, 2003, 1, 93).
APPLICATIONS:
Biochemistry Quinone outside Inhibitor. Respiratory electron transport inhibitor. Acts
by inhibiting cytochrome pathway (Complex III) between cytochrome b and cytochrome
c1, at the ubiquinol oxidising site. ModeofactionProtective, curative translaminar and
systemic fungicide, with secondary insecticidal activity. Uses Provides broad-spectrum
disease control, for example of cucumber downy mildew (Pseudoperonospora cubensis),
cucumber powdery mildew (Sphaerotheca fuliginea), cucumber grey mould (Botrytis
cinerea) and wheat powdery mildew (Blumeria graminis). Also active against Lepidoptera.
percutaneous LD50 for male and female rabbits >2000 mg/kg. Slight eye irritation; no skin
irritation (rabbits). Other Negative in Ames test.
SYP-Z071 497
2,4,5-T
Herbicide
Cl
Cl OCH2CO2H
Cl
Esters include: 2,4,5-T-butotyl (the 2-butoxyethyl), 2,4,5-T-butyl, 2,4,5-T-isoctyl (the iso-
octyl), and 2,4,5-T-butometyl (the 2-butoxy-1-methylethyl).
NOMENCLATURE:
Common name 2,4,5-T (BSI, E-ISO, (m) F-ISO, WSSA, JMAF); 2,4,5-T (also used by JMAF
for the butotyl ester)
IUPACname (2,4,5-trichlorophenoxy)acetic acid
Chemical Abstracts name (2,4,5-trichlorophenoxy)acetic acid CASRN[93765]
2,4,5-T; [3813147] 2,4,5-T-trolamine; [2008460] 2,4,5-T-triethylammonium; [25168
154] 2,4,5-T-isoctyl ECno2022733 SmilescodeOC(=O)COc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Composition Tech. is 94%. Mol. wt. 255.5; 367.7 (2,4,5-T-isoctyl) M.f. C8H5Cl3O3;
C16H21Cl3O3 (2,4,5-T-isoctyl) Form Colourless crystals. M.p.154-155C; 113-115C
(tris(2-hydroxyethyl)ammonium salt); solidifies 20C (tech., butyl ester) V.p. 7 104 mPa
(25C) Kow logP = 2.0 (ARS PPD, unstated pH) Henry 1.19 106 Pa m3 mol1 (calc.)
S.g./density 1.80 (20C) Solubility In water 150 mg/l (25C). In methanol 496, ethanol
548.2, diethyl ether 234.3, toluene 7.32, xylene 6.08, heptane 0.4 (all in g/l, 25C). The
alkali-metal and amine salts are readily soluble in water, but insoluble in petroleum oils. The
esters are practically insoluble in water, but soluble in petroleum oils. Stability Stable in
aqueous solution at pH 59. pKa 2.85 (J. Agr. & Food Chem., 26, 189 (1978))
COMMERCIALISATION:
Production Manufactured by condensation of sodium chloroacetate with sodium
2,4,5-trichlorophenoxide. At high temperatures the action of alkali on 2,4,5-trichlorophenol
can produce some 2,3,7,8-tetrachlorodibenzo-p-dioxin. History Herbicide reported by
C. L. Hamner & H. B. Tukey (Science, 1944, 100, 154). Introduced by Amchem Products Inc.
(later Rhne-Poulenc Agrochimie).
APPLICATIONS:
Biochemistry Similar to that of 2,4-D. ModeofactionSelective systemic herbicide with
hormone-like action, absorbed by the roots, bark, and foliage, and translocated through the
phloem. Uses Control of woody weeds, brush, and undergrowth in grassland and non-crop
land. Control of tree shoots and undergrowth in forestry. Treatment of tree stumps to
prevent regrowth. Amine formulations were used for weed control in rice.
Phytotoxicity Phytotoxic to almost all broad-leaved crops, and particularly
cotton, tomatoes, ornamentals, grapes, and fruit trees. Formulation types EC; SL .
Compatibility Mixing with solutions of heavy-metal salts, e.g. copper sulfate, can lead to
flocculation.
498 2,4,5-T
PRODUCTS:
Discontinued products Sylvoxone 850* (isoctyl ester) (Sopra); Weedone* (Rhne-
Poulenc).
ANALYSIS:
Product analysis by hplc (AOACMethods, 18th Ed., 980.08; J. Assoc. Off. Anal. Chem., 1980,
63, 379), by hplc, or glc or titration (CIPACHandbook, 1985, 1C, 2220), by glc of a suitable
ester (CIPACHandbook, 1985, 1C, 2072, 2257; 1994, F, 292319), or by an epinasty
determination (AOACMethods, 18th Ed., 960.10). Free phenol impurity determined by hplc
(CIPACHandbook, 1994, F, 362). Estimation of 2,3,7,8-tetrachlorodibenzo-p-dioxin content
has been studied (J. W. Edmunds et al., Pestic. Sci., 1973, 4, 101; P. G. Baker et al., ibid., 1981,
12, 297; CIPACHandbook, 1994, F, 352; ibid., 1985, C, 2284). Residues determined by glc
of a suitable ester (Pestic. Anal. Man., 1979, 1, 201-D; W. Specht & M. Tillkes, Fresenius Z.
Anal. Chem., 1980, 301, 300; 1981, 4307, 257; Anal. Methods Pestic. Plant Growth Regul., 1972,
6, 702; H. Lkke & P. Odgaard, Pestic. Sci., 1981, 12, 375; H. E. Munro, ibid., 1977, 8, 157).
In drinking water by conversion to methyl ester with diazomethane, then glc with ECD
(AOACMethods, 18th Ed., 992.32).
JMPR Evaln. 33 (1979), 37 (1981). PDS 13 (1975). IARC 41 (1986); Suppl. 7 (1987).
IARC Class 2B
Oral Acute oral LD50 for rats 3001700 mg/kg (depending on vehicle and rat strain);
for mice 3891380, dogs 100 mg/kg. Skin and eye Acute percutaneous LD50 for rats
>5000 mg/kg. NOEL In 2-y feeding trials no effect observed in rats receiving 30 mg/kg
diet; nor in 90 d trials in beagle dogs at 60 mg/kg diet. ADI/RfD (JMPR) 0.03 mg/kg b.w.
[1981], for 2,4,5-T containing not more than 0.01 mg tetrachlorodibenzodioxin (TCDD)/
kg; (EPA) cRfD 0.01 mg/kg b.w. [1989]. Water GV 0.009 mg/l. Other A contaminant,
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), produced foetal deaths in hamsters at 0.0091
mg/kg and it causes serious acne in man. Later methods of manufacture of 2,4,5-T limited
the amount of the contaminant to <0.01 mg/kg 2,4,5-T. Toxicity Class WHO (a.i.) II
ECClassification Xn; R22| Xi; R36/37/38| N; R50, R53 (for acid, salts or esters) PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LC50 (8 d) for bobwhite quail 2776 mg/kg diet; for ducks >4650 mg/kg
diet. Fish LC50 (96 h) for rainbow trout 350, carp 355 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, 50% is eliminated in the urine
within 23 h. There is no accumulation. Plants Degradation in plants is similar to that
for 2,4-D. This involves cleavage of the acetic acid moiety, ring hydroxylation of the
2,4,5-trichlorophenol so formed, and presumably ring opening and degradation. Soil/
Environment In soil, degradation occurs more slowly than for 2,4-D.
2,4,5-T 499
tar oils
Fungicide, herbicide, insecticide
NOMENCLATURE:
CASRN[65996829], coal tar oils; [8002297] tar oils (naphthalene oils, derived from
wood tar); different numbers apply to tar oils from other sources
PHYSICAL CHEMISTRY:
Composition Tar oils consist mainly of aromatic hydrocarbons, but contain components
soluble in aqueous alkali: the phenols or tar acids; and nitrogenous bases soluble in dilute
mineral acids: tar bases. They are produced by the distillation of tars resulting from the
high-temperature carbonisation of coal and of coke oven and blast furnace tars.
Form Brown to black liquids. B.p. Tar oils are the FRACtion boiling from 230C
upwards. S.g./density 1.051.11 (15C) Solubility Insoluble in water. Soluble in most
organic solvents and in dimethyl sulfate.
COMMERCIALISATION:
Production Tar oils are produced by the distillation of tars resulting from the high-
temperature carbonisation of coal and of coke oven and blast furnace tars.
History Although they have been used for wood preservation since 1890, the
introduction of the formulated products known as tar oil washes for crop protection, using
the heavy creosote and anthracene oil ranges, dates fromc.1920.
APPLICATIONS: Uses Control of overwintering stages (particularly eggs) of many
insects, e.g. aphids, suckers, moths, Mealybugs and scale insects, and overwintering diseases
on dormant pome, stone, cane and bush fruit, and grape vines. Moss and lichen are also
controlled. Also used as a hop defoliant, and as a game repellent in forestry.
Phytotoxicity Extremely phytotoxic, and so must only be used during the dormant
season. Formulation types EC; Emulsion.
PRODUCTS:
Discontinued products Clean-Up* (Miracle).
ANALYSIS:
Product analysis is by standard methods (MAFF Ref. Bk., 1958, No. 1, p. 81).
Skin and eye Irritating to skin, eyes and respiratory system. May cause dermatitis,
especially in sunlight. ECClassification Tar oils are classified as R45
ECOTOXICOLOGY:
Fish Toxic to fish.
500 tar oils

tazimcarb
Insecticide, molluscicide
NOMENCLATURE:
Common name tazimcarbe ((m) F-ISO); tazimcarb (BSI, E-ISO)
IUPACname N-methyl-1-(3,5,5-trimethyl-4-oxo-1,3-thiazolidin-2-ylideneamino-oxy)
formamide; 3,5,5-trimethyl-2-methylcarbamoyloxyimino-1,3-thiazolidin-4-one
Chemical Abstracts name 3,5,5-trimethyl-2,4-thiazolidinedione 2-[O-[(methylamino)
carbonyl]oxime]; formerly 2-[[[(aminocarbonyl)oxy]methyl]imino]-3,5,5-
trimethyl-4-thiazolidinone CASRN[40085572], formerly [62113035]
DevelopmentcodesPP505 SmilescodeCNC(=O)ON=C1SC(C)(C)C(=O)N1C
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Insecticide and molluscicide evaluated by ICI Agrochemicals.
APPLICATIONS:
2,4,5-TB
Herbicide
NOMENCLATURE:
Common name 2,4,5-TB (BSI, E-ISO, (m) F-ISO, WSSA)
IUPACname 4-(2,4,5-trichlorophenoxy)butyric acid
Chemical Abstracts name 4-(2,4,5-trichlorophenoxy)butanoic acid
CASRN[93801] SmilescodeOC(=O)CCCOc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 283.5 M.f. C10H9Cl3O3
COMMERCIALISATION:
History Herbicide.
2,4,5-TB 501
2,3,6-TBA
Herbicide
CO2H
C
l C
l
C
l
HRACO WSSA 4; benzoic acid (auxin)
NOMENCLATURE:
Common name 2,3,6-TBA (BSI, E-ISO, (m) F-ISO, WSSA); acide trichlorobenzoique
(optional alternative in France); TCBA (JMAF)
IUPACname 2,3,6-trichlorobenzoic acid
Chemical Abstracts name 2,3,6-trichlorobenzoic acid CASRN[50317]; [2078
424] 2,3,6-TBA-sodium ECno2000264 DevelopmentcodesHC-1281 (Heyden)
SmilescodeOC(=O)c1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade isc.60% 2,3,6-TBA. Mol. wt. 225.5 M.f. C7H3Cl3O2
Form Colourless crystals; (tech., colourless to buff, crystalline powder). M.p.125126C
(pure acid);c.80100C (tech.) B.p. Decomposes on distillation V.p. Very low at room
temperature; 3.2 Pa (100C) Solubility In water 7.7 g/l (22C). Readily soluble in
common organic solvents, e.g. acetone 60.7, benzene 23.8, chloroform 23.7, ethanol
63.7, methanol 71.7, xylene 21.0 (all in g/100 ml). Sodium salt, in water 440 g/kg (25C).
Stability Stable to light, and to temperatures up to 60C.
COMMERCIALISATION:
History Herbicide reported by H. J. Miller (Weeds, 1952, 1, 185). Introduced by the
Heyden Chemical Corp. and later by E. I. du Pont de Nemours & Co. (who now neither
manufacture nor market it), and currently available in mixtures with other herbicides.
Patents US 2848470 (1958); US 3081162 (1963)
APPLICATIONS:
Biochemistry Auxin type. ModeofactionSystemic growth-regulator herbicide with
hormone-like action, absorbed by the leaves and roots. Uses Used post-emergence, in
combinations with other growth regulator herbicides, in cereals and grass seed crops to
control broad-leaved annual and perennial weeds, including Bilderdykia convolvulus, Galium
aparine, Polygonum aviculare, P. persicaria, Chamomilla and Matricaria spp.
Compatibility Mixtures with fertilisers are not recommended.
PRODUCTS:
Discontinued products Trysben* (dimethylammonium salt) (DuPont);
Discontinuedmixtures Benzabor* (+borax) (US Borax).
502 2,3,6-TBA
ANALYSIS:
Product and salt analysis by titration or by glc (CIPACHandbook, 1985, 1C, 2225; ibid., 2257;
ibid., 1994, F, 292319); in mixture with MCPA, by titration or by glc of a derivative (ibid.,
1985, 1C, 2148). Residues determined by glc of a suitable derivative (J. J. Kirkland & H. L.
Pease, J. Agric. Food Chem., 1964, 12, 468).
Oral Acute oral LD50 for rats 1500, mice 1000, guinea pigs >1500, rabbits 600 mg/kg.
Skin and eye Acute percutaneous LD50 for rats >1000 mg/kg. NOEL In 6469 d feeding
trials, rats receiving 10000 mg/kg diet suffered a minor disturbance of water metabolism,
no trace of which was apparent at 1000 mg/kg diet. It is largely excreted unchanged in the
urine. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassification Xn; R22| N;
R51, R53
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens >1500 mg/kg. Fish Threshold value for toxic activity
100150 mg/l for perch and 300 mg/l for roach. One of several determining factors is the
content of the second, more toxic, 2,4,5- isomer in the active ingredient. Bees Not toxic
to bees.
ENVIRONMENTAL FATE:
Animals In mammals, excretion is mainly as the unchanged form in the urine.
Soil/Environment Very slow degradation in soil. A stable protein complex may possibly
be formed.
TDE
Insecticide
NOMENCLATURE:
Common name TDE (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane
Chemical Abstracts name 1,1-(2,2-dichloroethylidene)bis[4-chlorobenzene]
Other names DDD CASRN[72548] DevelopmentcodesMe-1700
SmilescodeClC(Cl)C(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 320.0 M.f. C14H10Cl4 B.p. 193C (Agchem. Desk Ref.) Solubility In water 0.05
ppm (25C) (Residue Reviews, 103, 1 (1988))
Stability Stable to hydrolysis; DT50 28 y (pH 7, 25C) (Agchem. Desk Ref.)
COMMERCIALISATION:
History Insecticide reported by P. Luger etal. (Helv. Chim. Acta, 1944, 27, 892). Introduced
by Rohm & Haas Co. (found in nature as a degradation product of DDT).
TDE 503
APPLICATIONS:
ModeofactionContact, ingested insecticide.
PRODUCTS:
Discontinued products Rhothane* (Rohm & Haas).
ANALYSIS:
See Pestic. Anal. Man., I, 303, 502.
tebutam
Herbicide
CH2
N CH(CH3)2
O C
C(CH3)3
HRACK1 WSSA 3; benzamide (mi)
NOMENCLATURE:
Common name tebutam (BSI, E-ISO); t(butame) ((m) F-ISO); butam (ANSI, WSSA); no
name (Japan)
IUPACname N-benzyl-N-isopropylpivalamide
Chemical Abstracts name 2,2-dimethyl-N-(1-methylethyl)-N-(phenylmethyl)
propanamide CASRN[35256850] ECno2524703
DevelopmentcodesGPC-5544 (Gulf); Ro 149480/000 (Roche); CGA 39625 (Ciba-
Geigy)
SmilescodeCC(C)N(Cc1ccccc1)C(=O)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 233.4 M.f. C15H23NO Form Light brown liquid. B.p. 9597C /0.1 mmHg
V.p.c.89 mPa (25C) Kow logP = 3 Henry 1.5 10-2 Pa m3 mol1 (calc.)
S.g./density 0.975 (20C) Solubility In water 0.79 g/l (pH 7, 20C). Readily soluble
in organic solvents, e.g. acetone, hexane, methanol, toluene, chloroform >500 g/l (25C).
Stability Chemically stable under normal storage conditions. Thermally stable at
temperatures below the boiling point. Stable to light. Stable to hydrolysis at pH 5, 7 and 9
(all at 25C). F.p. >80C (with 2% toluene)
COMMERCIALISATION:
History Herbicide reported by R. A. Schwartzbeck (Proc. Br. Crop Prot. Conf. Weeds,
1976, 2, 739). Introduced by Gulf Oil Chemicals Co. and later acquired by Dr R. Maag Ltd
(became Syngenta AG). Patents US 3974218; US 3707366 (to Gulf)
Manufacturers Syngenta
504 tebutam
APPLICATIONS:
Biochemistry Microtubule assembly inhibition. ModeofactionSelective herbicide,
acting by inhibition of weed germination and also through root uptake. Uses Pre-
emergence control of annual grasses, volunteer cereals and broad-leaved weeds in
oilseed rape and brassicas, at 2.83.6 kg/ha. Phytotoxicity A large number of crops are
susceptible, including cereals, maize, carrots, flax, onions, garlic, lettuce, melons, sorghum,
spinach, and sugar beet. Formulation types EC.
PRODUCTS:
Discontinued products Colzor* (Novartis); Comodor* (Novartis).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FID or by hplc.
Oral Acute oral LD50 for albino rats 6210, guinea pigs 2025 mg/kg. Skin and eye Acute
percutaneous LD50 for rats and albino rabbits >2000 mg/kg. A slight irritant to the eyes and
skin of rabbits. Inhalation LC50 for rats >2.18 mg/l air. There was no adverse effect when
albino rats were exposed to an aerosol (66% vol. mixture of tech. product and acetone).
NOEL (2 y) for rats 600, mice 3000 ppm. ADI/RfD (BfR) 0.3 mg/kg b.w. [1990].
ECOTOXICOLOGY:
Birds Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 mg/kg. Fish LC50
(96 h) for rainbow trout 23, bluegill sunfish 19, moonfish 18.7 mg/l. Algae LC50 (96 h) for
Scenedesmus subspicatus 82 mg/l. Bees Acute oral LD50 100 g/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, rapidly excreted in the urine and faeces.
Plants In plants, tebutam is rapidly metabolised. Soil/Environment Bound by the organic
matter of soil; DT50c.2 mo.
tecoram
Fungicide
NOMENCLATURE:
Common name tecoram (BSI)
IUPACname N,N,N,N-tetramethyl-N,N-ethylenedi(thiuram disulfide)
Chemical Abstracts name N,N,N,N-tetramethyl-4,9-dithioxo-2,3,10,11-tetrathia-5,8-
diazadodecanedithioamide CASRN[5836237]
SmilescodeCN(C)C(=S)SSC(=S)NCCNC(=S)SSC(=S)N(C)C
tecoram 505
PHYSICAL CHEMISTRY:
Mol. wt. 450.8 M.f. C10H18N4S8
COMMERCIALISATION:
History Fungicide evaluated by Aagrunol N.V.
PRODUCTS:
Discontinued products Azosan* (Aagrunol).
TEPP
IRAC1B
NOMENCLATURE:
Common name TEPP (BSI, E-ISO, (m) F-ISO, ESA, JMAF); ethyl pyrophosphate (BAN)
IUPACname tetraethyl pyrophosphate
Chemical Abstracts name tetraethyl diphosphate Other names TEP CASRN[107
493] ECno2034953 SmilescodeCCOP(=O)(OCC)OP(=O)(OCC)OCC
PHYSICAL CHEMISTRY:
Mol. wt. 290.2 M.f. C8H20O7P2 Form Colourless hygroscopic liquid; (tech. is a dark amber-
coloured mobile liquid). B.p. 124C /1 mmHg V.p. 21 mPa (20C)
S.g./density 1.185 (20C);c.1.2 (25C, tech.) Solubility Miscible with water and most
organic solvents; sparingly soluble in petroleum oils. Stability Rapidly hydrolysed by water,
DT50 6.8 h (pH 7, 25C). Decomposes at 170C with the formation of ethylene.
COMMERCIALISATION:
History Aphicide discovered in 1938 by G. Schrader & H. Kkenthal (cited by G. Schrader,
Phosphorsure-Ester). In 1943, I. G. Farbenindustrie AG introduced a derivative then
thought to be hexaethyl tetraphosphate (known as HETP) but since shown to contain
TEPP as the main insecticidal component.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionNon-systemic acaricide and
aphicide. Uses Acaricide and aphicide with a very brief persistence.
Formulation types AE .
PRODUCTS:
Discontinued products Nifos T* (Monsanto); Vapotone* (Chevron).
ANALYSIS:
Product analysis by selective hydrolysis (CIPACHandbook, 1970, 1, 667; AOACMethods, 18th
Ed., 949.06). Residues determined by glc (J. Crossley, Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 471).
506 TEPP
Oral Acute oral LD50 for rats 1.12 mg/kg. Skin and eye Acute percutaneous LD50 for
male rats 2.4 mg/kg. Toxicity Class WHO (a.i.) Ia ECClassification T+; R27/28| N; R50
ENVIRONMENTAL FATE:
Animals It is rapidly metabolised by animals.
terallethrin
Insecticide
CH3
O CH2 CH2
CH3 C O CH
CH3 H O
CH3 CH3
IRAC3
NOMENCLATURE:
Common name terallethrin (BSI, E-ISO); t(rall) ((f) F-ISO)
IUPACname (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl
2,2,3,3-tetramethylcyclopropanecarboxylate
Chemical Abstracts name ()-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-
1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate CASRN[15589318] unstated
stereochemistry DevelopmentcodesM-108
SmilescodeCC1=C(CC=C)C(=O)CC1OC(=O)C2C(C)(C)C2(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 276.4 M.f. C17H24O3 Form Light yellow oily liquid. V.p. 27 mPa (20C)
Solubility Insoluble in water. Soluble in organic solvents. Stability Unstable to light and
to alkali.
COMMERCIALISATION:
History Insecticide introduced by Sumitomo Chemical Co., Ltd.
Manufacturers Jiangsu Yangnong
APPLICATIONS:
neurons by interaction with the sodium channel. Uses Public health fumigant insecticide
used for control of houseflies and cockroaches.
ANALYSIS:
terallethrin 507
terbucarb
Herbicide
NOMENCLATURE:
Common name MBPMC (JMAF); terbucarb (BSI, E-ISO); terbucarbe ((m) F-ISO);
terbutol (WSSA)
IUPACname 2,6-di-tert-butyl-p-tolyl methylcarbamate
Chemical Abstracts name 2,6-bis(1,1-dimethylethyl)-4-methylphenyl methylcarbamate
CASRN[1918112] DevelopmentcodesHercules 9573
SmilescodeCNC(=O)Oc1c(cc(C)cc1C(C)(C)C)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 277.4 M.f. C17H27NO2
COMMERCIALISATION:
History Herbicide reported by A. H. Haubein & J. R. Hansen (J. Agric. Food Chem., 1965, 13,
555). Introduced by Hercules Inc. (later Nor-Am.).
PRODUCTS:
Discontinued products Azak* (Hercules).
terbuchlor
Herbicide
NOMENCLATURE:
Common name terbuchlor (BSI, E-ISO, ANSI, WSSA); terbuchlore ((m) F-ISO)
IUPACname N-butoxymethyl-6-tert-butyl-2-chloroacet-o-toluidide
Chemical Abstracts name N-(butoxymethyl)-2-chloro-N-[2-(1,1-dimethylethyl)-6-
methylphenyl]acetamide CASRN[4212935] DevelopmentcodesMON 0358; CP 46
358 SmilescodeCCCCOCN(C(=O)CCl)c1c(C)cccc1C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 325.9 M.f. C18H28ClNO2
COMMERCIALISATION:
History Herbicide evaluated by Monsanto Co.
508 terbuchlor
tetcyclacis
NOMENCLATURE:
Common name tetcyclacis (BSI, E-ISO, (m) F-ISO)
IUPACname rel-(1R,2R,6S,7R,8R,11S)-5-(4-chlorophenyl)-3,4,5,9,10-penta-
azatetracyclo[5.4.1.02,6.08,11]dodeca-3,9-diene
Chemical Abstracts name (3a,4,4a,6a,7,7a)-1-(4-chlorophenyl)-3a,4,4a,6a,7,7a-
hexahydro-4,7-methano-1H-[1,2]diazeto[3,4-f]benzotriazole CASRN[77788217]
DevelopmentcodesBAS 106W (BASF)
SmilescodeClc1ccc(cc1)N2N=NC3C4CC(C5N=NC54)C32
PHYSICAL CHEMISTRY:
Mol. wt. 273.7 M.f. C13H12ClN5 Form Colourless crystalline solid. M.p.190C (decomp.)
Solubility In water 3.7 mg/kg (20C). In chloroform 42, ethanol 2 (both in g/kg, 20C).
Stability Decomposed by sunlight and concentrated acid.
COMMERCIALISATION:
History Plant growth regulator reported by J. Jung etal. (Z. Acker-Pflanzenbau, 1980, 149,
128). Introduced by BASF AG. Patents DE 2615878; GB 1573161; US 4189434
APPLICATIONS:
Biochemistry Gibberellin and sterol biosynthesis inhibitor. ModeofactionPlant growth
retardant. Uses It was used for improvement of rice seedlings. Treated seedlings are more
compact and shorter than untreated ones and they show enhanced rooting and tillering
capacity after transplanting into the field. Formulation types SP.
PRODUCTS:
Discontinued products Ken byo* (BASF).
ANALYSIS:
Product analysis is by hplc with uv detection. Residues may be determined by glc with ECD
of a derivative.
>4640 mg/kg.
ECOTOXICOLOGY:
Algae EC50 (cell volume) for Chlorella fusca 5.2 ;mol/l (Pestic. Sci. (1996) 47, 337).
tetcyclacis 509
tetrachlorothiophene
Nematicide
NOMENCLATURE:
IUPACname tetrachlorothiophene (I)
Chemical Abstracts name (I) Other names TCTP CASRN[6012971]
DevelopmentcodesTD-183 SmilescodeClc1sc(Cl)c(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 221.9 M.f. C4Cl4S
COMMERCIALISATION:
History Nematicide developed by Pennwalt Corp.
PRODUCTS:
Discontinued products Penphene* (Pennwalt).
tetrachlorvinphos
Cl O
P(OCH3)2
C (Z)- isomer
H C O
Cl
Cl
IRAC1B Cl
NOMENCLATURE:
Common name tetrachlorvinphos (BSI, E-ISO, (m) F-ISO); stirofos (ESA); CVMP (JMAF)
IUPACname (Z)-2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate
Chemical Abstracts name (Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl
phosphate CASRN[22248799] tetrachlorvinphos; [22350761] the analogous (E)-
isomer; [961115] mixed (Z)- +(E)- isomers DevelopmentcodesSD 8447 (Shell)
SmilescodeCOP(=O)(OC)O/C(=C\Cl)/c1cc(Cl)c(Cl)cc1Cl;without
stereochemistry:COP(=O)(OC)OC(=CCl)c1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade is typically 98% pure. Mol. wt. 366.0 M.f. C10H9Cl4O4P
Form Tech. is an off-white crystalline solid. M.p.9497C V.p. 0.0056 mPa (20C)
Henry 1.86 104 Pa m3 mol1 (calc.) Solubility In water 11 mg/l (20C). In acetone
<200, chloroform, dichloromethane 400, xylene <150 (all in g/kg, 20C). Stability Stable
<100C; slowly hydrolysed (50C), DT50 54 d (pH 3), 44 d (pH 7), 80 h (pH 10.5).
510 tetrachlorvinphos
COMMERCIALISATION:
History Insecticide reported by R. R. Whetsone etal. (J. Agric. Food Chem., 1966, 14,
352). Introduced by Shell Chemical Company, USA (later DuPont Agricultural Products,
who transferred rights to Fermenta Animal Health Co., which became Boehringer
Ingelheim Vetmedica, Inc., and to Hartz Mountain for pet uses). Patents US 3102842
Manufacturers Shanghai MCC
APPLICATIONS:
and acaricide with contact and stomach action. Uses A selective insecticide controlling
Lepidoptera and Diptera in fruit; and Lepidoptera in cotton, maize, rice, tobacco and
vegetables. With certain exceptions, not highly active against Hemiptera and other sucking
pests and, because of rapid breakdown, is not effective against soil-dwelling pests. It is used
against Muscidae in dairies and in livestock barns, against certain ectoparasites on poultry,
and against pests of stored products. Also used against insects that damage forests and
pasture. Phytotoxicity Russetting may occur on Golden Delicious apples under certain
conditions. Formulation types DP; EC; SC. WP. Compatibility Incompatible with
dodine and with alkaline materials.
PRODUCTS:
Discontinued products Appex* (Shionogi); Debantic* (ISK Biosciences); Gardcide*
(Cyanamid); Gardona* (crop protection use) (BASF); Rabon* (DuPont); Rabond*
(Cyanamid).
ANALYSIS:
Product analysis by glc with FID; details available from BASF. Residues of tetrachlorvinphos
and its major metabolites in plants determined by glc (Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 297; K. I. Beynon & A. N. Wright, J. Sci. Food Agric., 1969, 20, 250; K. I. Beynon
et al., Pestic. Sci., 1970, 1, 250, 254, 259). See also Pestic. Anal. Man., II, 180.252, 186.950. In
drinking water by glc with NPD (AOACMethods, 18th Ed., 991.07).
EHC 63 (1986; a general review of organophosphorus insecticides). IARC 30 (1983).
IARC Class 3
percutaneous LD50 for rabbits >2500 mg/kg. NOEL NOAEL for rats 4.23 mg/kg b.w. (EPA
RED); NOEL (2 y) for rats 125 mg/kg diet, for dogs 200 mg/kg diet. Reproduction studies
on rats receiving 1000 mg/kg diet showed no adverse effects. ADI/RfD (EPA) aRfD 0.067,
cRfD 0.0423 mg/kg b.w. [2006]. Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Acute oral LD50 for Chukar partridges and mallard ducks >2000 mg/kg, for various
other birds 15002600 mg/kg. Fish LC50 (24 h) for five different species 0.36.0 mg/l.
Bees Toxic to bees.
tetrachlorvinphos 511
ENVIRONMENTAL FATE:
Animals In mammals, rapid metabolism occurs, with elimination of the metabolites
within a few days. Metabolites found in the urine of dogs and rats include
2,4,5-trichlorophenylethanediol glucuronide, further glucuronic acid derivatives,
2,4,5-trichloromandelic acid, and 2-chloro-1-(2,4,5-trichlorophenyl)vinylmethyl hydrogen
phosphate. No significant residues of tetrachlorvinphos or its metabolites are found in
milk or tissues of exposed animals. Soil/Environment For a review on metabolism and
breakdown in plants, animals and soil, see K. I. Beynon et al., Residue Rev., 1973, 47, 55.
tetrafluron
Herbicide
NOMENCLATURE:
Common name tetrafluron (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname 1,1-dimethyl-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]urea
Chemical Abstracts name N,N-dimethyl-N-[3-(1,1,2,2-tetrafluoroethoxy)
phenyl]urea CASRN[27954376], formerly [34766295] and [36510948]
DevelopmentcodesHoe 2991 SmilescodeCN(C)C(=O)Nc1cccc(OC(F)(F)C(F)F)c1
PHYSICAL CHEMISTRY:
Mol. wt. 280.2 M.f. C11H12F4N2O2
COMMERCIALISATION:
O,O,O,O-tetrapropyl dithiopyrophosphate
Insecticide
IRAC1B
NOMENCLATURE:
IUPACname O,O,O,O-tetrapropyl dithiopyrophosphate
Chemical Abstracts name tetrapropyl thiodiphosphate; thiodiphosphoric acid
([(HO)2P(S)]2O) tetrapropyl ester Other names NPD CASRN[3244904]
ECno2218170 DevelopmentcodesASP-51 (Stauffer)
SmilescodeCCCOP(=S)(OCCC)OP(=S)(OCCC)OCCC
PHYSICAL CHEMISTRY:
Composition Tech. is 9396%. Mol. wt. 378.4 M.f. C12H28O5P2S2 Form Tech. is a straw
to amber-coloured liquid, with a faint aromatic odour. B.p.c.170C /1 mmHg
V.p. c.13 mPa (25C) S.g./density 1.1191.123 (20C) Solubility In water 30 mg/l
(20C). Miscible with acetone, ethanol, kerosene, 4-methylpentan-2-one, xylene.
Stability Stable <100C. DT50 32 d (pH 7 buffer, 40C).
512
O,O,O,O-tetrapropyl dithiopyrophosphate
COMMERCIALISATION:
History Insecticide reported by A. D. F. Toy (J. Am. Chem. Soc., 1951, 73, 4670). Introduced
by Stauffer Chemical Co. (later ICI Americas). Patents US 2663722
APPLICATIONS:
Uses Insecticide particularly effective at 8.6. kg/ha for the control of Blissus leucopterus in
turf. Formulation types EC; GR .
PRODUCTS:
Discontinued products Aspon* (Stauffer); Sod* (Chevron).
ANALYSIS:
Product analysis by glc with FID (R. D. Mills & M.Yuan, Anal. Methods Pestic. Plant Growth
Regul., 1984, 13, 149). Residues in soil and turf determined by glc (idem, ibid.).
Oral Acute oral LD50 for male albino rats 2800, female rats 740 mg/kg.
Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Mildly irritating to skin
and non-irritating to eyes (rabbits). Other In 90 d feeding trials at sublethal rates, rats
showed some depression of red blood cell cholinesterase. ECClassification Xn; R21/22
ENVIRONMENTAL FATE:
Soil/Environment Persistent in soil.
tetrasul
Acaricide
NOMENCLATURE:
Common name tetradisul (Canada); diphenylsulphide (JMAF); tetrasul (BSI, E-ISO, (m)
F-ISO, ESA)
IUPACname 4-chlorophenyl 2,4,5-trichlorophenyl sulfide
Chemical Abstracts name 1,2,4-trichloro-5-[4-(chlorophenyl)thio]benzene
CASRN[2227136] DevelopmentcodesV-101 (N.V. Philips-Roxane)
SmilescodeClc1ccc(Sc2cc(Cl)c(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY:
Composition Tech. is 77.5%. Mol. wt. 324.1 M.f. C12H6Cl4S Form Tech. is a cream to
yellow-brown solid. M.p.88.488.6C; (tech., 7585C) V.p. 0.10 mPa (20C)
Henry 1.08 Pa m3 mol1 (calc.) Solubility In water 0.03 mg/l (20C). In 1,2-dichloroethane
274, ethanol 20, xylene 400 (all for tech., in g/l, 20C). Stability Stable at ambient
temperature in the dark; it is slowly oxidised via the corresponding sulphoxide to
tetradifon under prolonged exposure to sunlight. No conversion after 30 min at 90C in
a methanolic potassium hydroxide solution; <2% decomposition after 7 d at pH 6 as a 25
mg/l suspension in water.
tetrasul 513
COMMERCIALISATION:
History Acaricide reported by J. Meltzer & F. C. Dietvoorts (Proc. Int. Congr. Crop Prot.,
4th, 1957, 1, 669). Introduced by N.V. Philips-Roxane (later Uniroyal Chemical Co., Inc.).
Patents NL 94329; US 3054719
APPLICATIONS:
ModeofactionContact acaricide. Uses For the control of various phytophagous mites
which hibernate in the winter egg form. It is necessary to apply it when the winter eggs
were about to hatch. It was recommended for use on cucumber, bush fruit, top fruit and
grapes at 36 g/100 l. Formulation types WP.
PRODUCTS:
Discontinued products Animert V101* (DuPont).
ANALYSIS:
Product analysis by glc (L. R. Mitchell, J. Assoc. Off. Anal. Chem., 1976, 59, 209). Residues
determined by glc (idem, ibid.; AOACMethods, 18th Ed., 976.23). See also Pestic. Anal. Man., I,
303.
Oral Acute oral LD50 for male rats 8250, female rats 6810, male and female mice 5010,
male guinea pigs 8250, female guinea pigs 8800 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits >2000 mg/kg. NOEL (2 y) for rats 10 mg/kg diet. In 90 d feeding trials,
beagle-dogs tolerated 200 mg/kg diet. In a 3-generation study on rats, NOEL 20 mg/kg
diet Toxicity Class WHO (a.i.) U
thiadifluor
Fungicide
NOMENCLATURE:
Common name thiadifluor (BSI, E-ISO, (m) F-ISO)
IUPACname 3-(4-chlorophenyl)-N2-methyl-N4,N5-bis(trifluoromethyl)-1,3-thiazolidine-
2,4,5-triylidenetriamine
Chemical Abstracts name N,N-[3-(4-chlorophenyl)-2-(methylimino)-4,5-
thiazolidinediylidene]bis[1,1,1-trifluoromethanamine] CASRN[80228939]
DevelopmentcodesSLJ 4027a
SmilescodeCN=C1SC(=NC(F)(F)F)C(=NC(F)(F)F)N1c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 353.3 M.f. C12H7F6N4S
COMMERCIALISATION:
514 thiadifluor
thiazafluron
Herbicide
F3C S N CONHCH3
N N CH3
NOMENCLATURE:
Common name thiazafluron (BSI, E-ISO, (m) F-ISO); thiazfluron (Canada)
IUPACname 1,3-dimethyl-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea
Chemical Abstracts name N,N-dimethyl-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]
urea CASRN[25366238] ECno2469014 DevelopmentcodesGS 29 696
SmilescodeCNC(=O)N(C)c1nnc(s1)C(F)(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 240.2 M.f. C6H7F3N4OS Form Colourless crystals. M.p.136137C
V.p. 0.27 mPa (20C) Kow logP = 1.82 Henry 3.09 105 Pa m3 mol1 (calc.)
S.g./density 1.6 (20C) Solubility In water 2.1 g/l (20C). In ethanol 300, methanol 257,
n-octanol 60, DMF 600, xylene <50, benzene 12, hexane dichloromethane 146 (all in g/kg,
20C). Stability No significant hydrolysis in 28 d at pH 1, pH 5 or pH 7.
COMMERCIALISATION:
History Herbicide reported by G. Mller etal. (C. R. Journ. Etud. Herbic. Conf. COLUMA,
7th, 1973, p. 32). Introduced by Ciba-Geigy AG. Patents BE 725984; GB 1254468
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor. ModeofactionNon-
selective soil-herbicide, absorbed principally by the roots. Uses Control of most annual
and perennial grasses and broad-leaved weeds, in addition to woody plants such as shrubs
and bushes, on uncultivated land, industrial land, railway tracks, etc. Applied either pre-
emergence or early post-emergence at 28 kg/ha in moist and temperate and 612 kg/ha
in warm and dry regions. Formulation types GR; WP.
PRODUCTS:
Discontinued products Erbotan* (Ciba-Geigy).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FPD.
LD50 for rats >2150 mg/kg. Slight irritant to eyes, but non-irritant to skin (rabbits).
Inhalation LC50 of 80% formulation for rats >0.35 mg/l. NOEL (90 d) for rats 160 mg/kg
diet (11 mg/kg daily); (105 d) for dogs 250 mg/kg diet (8 mg/kg daily).
thiazafluron 515
Toxicity Class WHO (a.i.) II ECClassification Xn; R22| N; R50, R53

ECOTOXICOLOGY:
Birds Slightly toxic to birds. Fish LC50 (96 h) for rainbow trout 82, bluegill sunfish and
crucian carp >100 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soils, DT50 50200 d.
thicrofos
Insecticide
IRAC1B
NOMENCLATURE:
Common name thicrofos (BSI, E-ISO, (m) F-ISO)
IUPACname S-(6-chloro-3,4-dihydro-2H-1-benzothi-in-4-yl) O,O-diethyl
phosphorothioate
Chemical Abstracts name S-(6-chloro-3,4-dihydro-2H-1-benzothiopyran-4-yl)
O,O-diethyl phosphorothioate CASRN[41219323] unstated stereochemistry
DevelopmentcodesHoe 20 906
SmilescodeCCOP(=O)(OCC)SC1CCSc2ccc(Cl)cc12
PHYSICAL CHEMISTRY:
Mol. wt. 352.8 M.f. C13H18ClO3PS2
COMMERCIALISATION:
History Insecticide evaluated by Hoechst AG.
APPLICATIONS:
thicyofen
Fungicide
O S CN
CH3CH2S
Cl
CN
NOMENCLATURE:
Common name thicyof(ne) ((m) F-ISO); thicyofen (BSI, E-ISO)
IUPACname ()-3-chloro-5-ethylsulfinylthiophene-2,4-dicarbonitrile
Chemical Abstracts name ()-3-chloro-5-(ethylsulfinyl)-2,4-thiophenedicarbonitrile
CASRN[116170300] unstated stereochemistry DevelopmentcodesPH 5107; DU
516 thicyofen
510 311 (Duphar) SmilescodeCCS(=O)c1sc(C#N)c(Cl)c1C#N

PHYSICAL CHEMISTRY:
Mol. wt. 244.7 M.f. C8H5ClN2OS2 Form Solid. M.p.130C V.p. <1 mPa (20C)
Kow logP = 2.54 Henry <1.02 103 Pa m3 mol1 (calc.) Solubility In water 240 mg/l
(20C).
COMMERCIALISATION:
History Fungicide reported by T. W. Hofman etal. (Proc. 1990 Br. Crop Prot. Conf. - Pests
Dis., 2, 431). Introduced by Duphar B.V. (later Uniroyal Chemical Co., Inc.).
APPLICATIONS:
Biochemistry Multi-site inhibitor. Uses Non-systemic seed treatment for control
of Fusarium and Pythium spp., Pyrenophora graminea, and Tilletia caries in cereals, maize
and cotton. Also used as a soil treatment for control of Pythium spp. in flower bulbs.
Formulation types SC.
percutaneous LD50 for rats >2000 mg/kg. Other Non-mutagenic in in vitro tests.
ECOTOXICOLOGY:
Birds Acute oral LD50 for bobwhite quail 216 mg/kg. Dietary LC50 for bobwhite quail and
mallard ducks >5620 mg/kg.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly degraded in soil, DT50 <30 d.
thidiazimin
Herbicide
HRACE WSSA 14; thiadiazole
NOMENCLATURE:
Common name thidiazimin (BSI, E-ISO); thidiazimine ((f) F-ISO)
IUPACname (Z)-6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c][1,2,4]thiadiazol-3-
ylideneamino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
Chemical Abstracts name 6-[(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c][1,2,4]
thiadiazol-3-ylidene)amino]-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
CASRN[123249434] DevelopmentcodesSN 124 085 SmilescodeCC1(C)
Cc2nsc(=Nc3cc4N(CC#C)C(=O)COc4cc3F)n2C1
PHYSICAL CHEMISTRY: Mol. wt. 372.4 M.f. C18H17FN4O2S Form Colourless
crystals. M.p.158C V.p. 5.0 10-8 mPa (25C) Kow logP = 3.0 (pH 7) Henry 2.82
109 Pa m3 mol1 (calc.) Solubility In water (6.6 0.5) 103 g/l (pH 7, 25C).
pKa 2.60.1 (conjugate acid)
thidiazimin 517
COMMERCIALISATION:
History Herbicide reported by R. Weiler etal. (Proc. Br. Crop Prot. Conf. Weeds, 1993, 1,
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. ModeofactionContact herbicide
with rapid action. Uses Post-emergence control of broad-leaved weeds in winter cereals,
particularly effective against Lamium purpureum, Veronica hederifolia, Veronica persica and
Viola arvensis. Application rates were 2040 g/ha. Formulation types SC.
rats >>5000 mg/kg. No skin or eye irritancy (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation LC50 for rats >4.89 mg/l. Other Non-teratogenic and non-genotoxic.
ECOTOXICOLOGY:
Birds Low toxicity to birds.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 3070 d, depending on soil type. Soil adsorption coefficient
(Koc) 7001200 ml/g.
thiocarboxime
NOMENCLATURE:
Common name thiocarboxime (BSI, E-ISO, (f) F-ISO)
IUPACname 3-[1-(methylcarbamoyloxyimino)ethylthio]propiononitrile
Chemical Abstracts name 2-cyanoethyl N-[[(methylamino)carbonyl]oxy]
ethanimidothioate CASRN[25171635] DevelopmentcodesWL 21 959; SD 17250
SmilescodeCNC(=O)ON=C(C)SCCC#N
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Insecticide and acaricide evaluated by Shell Research Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Talcord* (Shell).
518 thiocarboxime
thiochlorfenphim
Fungicide
NOMENCLATURE:
Common name thiochlorfenphim (BSI, E-ISO); thiochlorphenphim ((f) F-ISO);
thiochlorphenphime (France)
IUPACname N-(4-chlorophenylthiomethyl)phthalimide
Chemical Abstracts name 2-[[(4-chlorophenyl)thio]methyl]-1H-isoindole-1,3(2H)-
dione CASRN[19378586] DevelopmentcodesBAY 66 109; SRA 3208
SmilescodeClc1ccc(SCN2C(=O)c3ccccc3C2=O)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 303.8 M.f. C15H10ClNO2S
COMMERCIALISATION:
History Fungicide evaluated by Bayer AG.
2-thiocyanatoethyl laurate
Insecticide
NOMENCLATURE:
IUPACname 2-thiocyanatoethyl laurate
Chemical Abstracts name 2-thiocyanatoethyl dodecanoate CASRN[301111]
SmilescodeCCCCCCCCCCCC(=O)OCCSC#N
PHYSICAL CHEMISTRY:
Mol. wt. 285.5 M.f. C15H27NO2S
COMMERCIALISATION:
History Insecticide developed by Rohm & Haas Co.
PRODUCTS:
Discontinued products Lethane 60* (Rohm & Haas).
2-thiocyanatoethyl laurate 519

thiofanox
O C(CH3)3
CH3NH C O N C
CH2SCH3
IRAC1A; oxime carbamate

NOMENCLATURE:
Common name thiofanocarb (Republic of South Africa); thiofanox (BSI, E-ISO, (m) F-ISO,
ANSI, ESA)
IUPACname 3,3-dimethyl-1-methylthiobutanone O-methylcarbamoyloxime;
1-(2,2-dimethyl-1-methylthiomethylpropylideneamino-oxy)-N-methylformamide
Chemical Abstracts name 3,3-dimethyl-1-(methylthio)-2-butanone O-[(methylamino)
carbonyl]oxime CASRN[39196184] ECno2543464
DevelopmentcodesDS 15 647 (Diamond Shamrock)
SmilescodeCNC(=O)ON=C(CSC)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 218.3 M.f. C9H18N2O2S Form Colourless solid, with a pungent odour. M.p.56.5
57.5C V.p. 22.6 mPa (25C) Solubility In water 5.2 g/l (22C). Readily soluble in
chlorinated and aromatic hydrocarbons, ketones and non-polar solvents. Slightly soluble
in aliphatic hydrocarbons. Stability Stable to heat under normal storage conditions.
Relatively stable to hydrolysis at pH 59 (under 30C). Decomposed by strong acids and
alkalis.
COMMERCIALISATION:
History Insecticide reported by R. L. Schauer (Proc. Br. Insectic. Fungic. Conf., 7th, 1973, 2,
713). Relationship between chemical structure and biological activity of analogues reported
by T. A. Magee & L. E. Limpel (J. Agric. Food Chem., 1977, 25, 1376). Introduced by Diamond
Shamrock Chemical Co. Later sold to Rhne-Poulenc Agrochimie (now Bayer AG).
Manufacturers Bayer CropScience
APPLICATIONS:
acaricide. Uses Soil application for control of black bean aphids, beet leaf miners, Flea
beetles and pygmy mangold beetles on beet; flea beetles on rape; aphids, capsids, flea
beetles, colorado beetle and leafhoppers on potatoes; aphids, midges, flea beetles, soil-
inhabiting larvae and spider mites on cotton; aphids and spider mites in floriculture, etc.
Applied at rates in the range 0.43 kg/ha. Formulation types GR .
PRODUCTS:
Discontinued products Benelux* (ISK Biotech); Dacamox* (Bayer CropScience).
520 thiofanox
ANALYSIS:
Residues, which are likely to include thiofanox, its sulfoxide and sulfone, are oxidised to
the sulfone, which is determined by glc (W. T. Chin, J. Agric. Food Chem., 1975, 23, 963; M. B.
Szalkowski et al., J. Chromatogr., 1976, 128, 426).
Oral Acute oral LD50 for albino rats 8.5 mg/kg. Skin and eye Acute percutaneous LD50
for albino rabbits 39 mg/kg. NOEL (90 d) for rats and beagle dogs 1 mg/kg daily. Clinical
symptoms of reversible cholinesterase inhibition at 4.0 mg/kg daily, lasting for 34 hours.
Weight gain of rats receiving 100 mg/kg diet was not affected. ADI/RfD (EPA) 0.0003 mg/
kg b.w. [1988]. Toxicity Class WHO (a.i.) Ib EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks 109, bobwhite quail 43 mg/kg. Fish LC50 (96 h)
for rainbow trout 0.13, bluegill sunfish 0.33 mg/l. Bees Not toxic to bees when used as
directed.
ENVIRONMENTAL FATE:
Animals Metabolism of carbamate insecticides is reviewed (M. Cool & C. K. Jankowski
in Insecticides). Plants Metabolism in plants is the same as in soil. The duration of activity
following absorption through the roots is at least 8 weeks. Soil/Environment In soil, the
methylthio group is rapidly oxidised to the sulfoxide and, further, to the sulfone. Further
degradation occurs to water-soluble metabolites.
thionazin
IRAC1B
NOMENCLATURE:
Common name thionazin (BSI, E-ISO); thionazine ((m) F-ISO)
IUPACname O,O-diethyl O-pyrazin-2-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-pyrazinyl phosphorothioate
CASRN[297972] ECno2060496 DevelopmentcodesExperimental Nematicide
18 133 (Cyanamid) SmilescodeCCOP(=S)(OCC)Oc1cnccn1
PHYSICAL CHEMISTRY:
Composition Tech. isc.90%. Mol. wt. 248.2 M.f. C8H13N2O3PS Form Colourless to
pale yellow liquid; (tech. is a dark brown liquid). M.p.-1.67C V.p. 400 mPa (30C)
Henryc.8.71 10-2 Pa m3 mol1 (calc.) S.g./density 1.207 (25C); tech. 1.2041.210
thionazin 521
(25C) Solubility In water 1.14 g/l (27C). Miscible with most organic solvents.
Stability Readily hydrolysed by alkali (pH >9).
COMMERCIALISATION:
History Nematicide introduced by American Cyanamid Co. Patents US 2918468; US
2938831; US 3091614
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Soil insecticide and nematicide effective
against a number of plant-parasitic as well as free-living nematodes, including those
attacking buds, bulbs, leaves and roots, as well as against soil dwelling pests such as
root maggots and symphylids and foliar insects such as aphids and leaf miners. When
incorporated in mushroom compost at spawning it is effective against mushroom flies. It is
of short persistence. Formulation types EC; GR .
PRODUCTS:
Discontinued products Bulb Dip* (Neals); Cynem* (Cyanamid); Nemafos*
(Cyanamid); Zinophos* (Cyanamid).
ANALYSIS:
Product analysis is by hydrolysis with fluorimetric determination of the sodium salt
of pyrazin-2-ol (U. Kiigemagi et al., J. Agric. Food Chem., 1963, 11, 293). Residues may be
determined by glc (D. R. Coahran, Bull. Environ. Contam. Toxicol., 1966, 1, 208).
for rats 11 mg/kg. NOEL In feeding trials, rats receiving 25 mg/kg diet for 30 d and then
50 mg/kg diet for 60 d showed a moderate depression in growth rate, but no abnormal
behavioural reactions. ADI/RfD (EPA) 0.00005 mg/kg b.w. [1987]. Toxicity Class WHO
(a.i.) Ia ECClassification T+; R27/28
ECOTOXICOLOGY:
Birds LC50 (5 d) for bobwhite quail 65, pheasants 72 mg/kg diet. Fish LC50 (48 h) for
harlequin fish 0.09 mg (as 480 g/l EC)/l. Bees LD50 (topical) for honeybees 42 ng/l.
thiophanate
Anthelmintic, fungicide
FRAC1, B1
NOMENCLATURE:
Common name thiophanate (BSI, E-ISO, (m) F-ISO, JMAF, BAN); thiophanate-(thyl) ((m)
France)
522 thiophanate
IUPACname diethyl 4,4-(o-phenylene)bis(3-thioallophanate)

Chemical Abstracts name diethyl [1,2-phenylenebis(iminocarbonothioyl)]
bis[carbamate] CASRN[23564069] DevelopmentcodesNF 35 (Nippon Soda)
SmilescodeCCOC(=O)NC(=S)Nc1ccccc1NC(=S)NC(=O)OCC
PHYSICAL CHEMISTRY: Mol. wt. 370.5 M.f. C14H18N4O4S2 Form Colourless
crystalline solid. M.p.195C (decomp.) Solubility Almost insoluble in water; sparingly
soluble in most organic solvents. Stability Forms unstable solutions of salts with aqueous
alkali and complexes with divalent transition metal ions, for example copper.
COMMERCIALISATION:
History Fungicide reported by K. Ishii (Abstr. Int. Congr. Plant Prot., 7th, Paris, 1970, p.
200); reviewed (idem, Jpn. Pestic. Inf., 1971, No. 7, p. 27). Introduced by Nippon Soda Co.,
Ltd. For thiophanate-methyl, see Main Entries. Patents DE 1930540
APPLICATIONS:
Biochemistry Carbendazim (q.v.) precursor. ModeofactionSystemic fungicide.
Uses Effective against Venturia spp. on apple and pear crops, powdery mildews, Botrytis and
sclerotinia spp. on various crops. Also used as an anthelminthic. Formulation types WP.
PRODUCTS:
Discontinued products Cercobin* (Nippon Soda); Nemafax* (anthelmintic) (May &
Baker); Topsin* (Nippon Soda); Verdamax* (anthelmintic) (May & Baker).
ANALYSIS:
Product analysis by uv spectrometry.
percutaneous LD50 for male and female rats >15000 mg/kg. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Plants In plants it is converted into ethyl benzimidazol-2-ylcarbamate.
thioquinox
NOMENCLATURE:
Common name thioquinox (BSI, E-ISO, (m) F-ISO, ESA)
IUPACname 1,3-dithiolo[4,5-b]quinoxaline-2-thione (I)
DevelopmentcodesBayer 30 686; Ss 1451 SmilescodeS=c1sc2nc3ccccc3nc2s1
thioquinox 523
PHYSICAL CHEMISTRY:
Mol. wt. 236.3 M.f. C9H4N2S3
COMMERCIALISATION:
History Acaricide and fungicide reported by G. Unterstenhfer (Hoefchen-Briefe, (Engl.
Ed.), 1960, 13, 207) and by K. Sasse (ibid., p. 197). Introduced by Bayer AG.
PRODUCTS:
Discontinued products Eradex* (Bayer); Eraziton* (Bayer).
tiocarbazil
Herbicide
CH3
CH3CH2CH S CH2
N C
CH3CH2CH O
CH3
NOMENCLATURE:
Common name tiocarbazil (BSI, E-ISO, (m) F-ISO)
IUPACname S-benzyl di-sec-butylthiocarbamate
Chemical Abstracts name S-(phenylmethyl) bis(1-methylpropyl)carbamothioate
CASRN[36756793] ECno2531904 DevelopmentcodesM 3432 (Agrimont)
SmilescodeCCC(C)N(C(C)CC)C(=O)SCc1ccccc1
PHYSICAL CHEMISTRY:
Mol. wt. 279.4 M.f. C16H25NOS Form Colourless liquid, with aromatic odour.
B.p. 130132C /0.1 mmHg V.p. 93 mPa (50C) Kow logP = 4.4 S.g./density 1.023
(20C) Solubility In water 2.5 mg/l (30C). Miscible with polar and non-polar organic
solvents. Stability Stable to hydrolysis at pH 5.68.4. Slightly decomposed after 30 days
at 40C in aqueous ethanol at pH 1.5. Stable to storage for 60 days at 40C, and for 100
hours in aqueous solution exposed to sunlight.
COMMERCIALISATION:
History Herbicide reported by N. Caracalli etal. (Proc. Congr. Risicultura, 8th, 1973, p.
446). Introduced by Montedison S.p.A. (later Isagro S.p.A.) in Italy (1974).
Patents IT 907710; DE 2144700
524 tiocarbazil
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). ModeofactionSelective
herbicide, absorbed by the roots and coleoptiles. Uses Control of Echinochloa spp., Lolium
perenne, Cyperus spp., and other monocotyledonous weeds in rice paddy fields. Applied
pre- or post-emergence at 4 kg/ha, or as a seed dressing. Phytotoxicity Non-phytotoxic
to rice. Formulation types EC; GR; SL; Seed treatment.
PRODUCTS:
Discontinued products Drepamon* (Isagro).
ANALYSIS:
Product and residue analysis by tlc (R. Fabbrini & G. Galluzzi, Anal. Methods Pestic. Plant
Growth Regul., 1980, 11, 307). Product analysis also by glc method; details available from
Isagro.
EHC 76 (1988) is a general review of thiocarbamates. EU Status (1107/2009) Not
Oral Acute oral LD50 for rats, rabbits, and guinea pigs >10000 mg tech./kg, for mice
8000 mg/kg. Skin and eye Acute percutaneous LD50 for rats and rabbits >1200 mg/kg.
Inhalation LC50 for rats >0.18 mg/l air. NOEL In 2 y feeding trials, albino rats and beagle
dogs receiving 1000 mg tech./kg diet suffered no ill-effect except for a slight weight loss
in male dogs. No effect on reproduction in albino rats receiving 300 mg/kg diet for 3
generations. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD50 for chickens, pheasants, quail >10000 mg tech./kg. Fish LC50 in
several fish species 8 mg/l. Other aquatic spp. LC50 for the mollusc Australorbis glabratus
>60 mg/l. Bees Not hazardous for honeybees.
ENVIRONMENTAL FATE:
Animals Tiocarbazil, when administered orally at the dose of 1 g/kg, is almost totally
eliminated 7 days after treatment, either as such in the faeces or as products deriving
from its metabolism, through the urine. In the blood and in the main organs, minimum
concentrations of the product and of its metabolites have been found 48 hours after
treatment. Plants Tiocarbazil undergoes extensive metabolism in rice: 3 compounds have
been identified in plants (except caryopsides): N,N-di-sec-butylcarbamoylthiolglycolic acid,
N,N-di-sec-butylcarbamoyl benzylsulfoxide, and N,N-di-sec-butylcarbamoyl benzylsulfone
(the first by oxidation of the benzene ring, the other two by oxidation of the sulfur atom).
Soil/Environment Tiocarbazil is strongly adsorbed by the soil (where it largely localises
in the uppermost layer), Kom 1711, and undergoes a rapid degradation due to the attack
of soil micro-organisms; 50% of tiocarbazil applied is no longer present in the soil/water
system of a rice field 815 days after treatment.
tiocarbazil 525
tioclorim
Herbicide
NOMENCLATURE:
Common name tioclorime ((f) F-ISO); tioclorim (BSI, E-ISO)
IUPACname 6-chloro-5-(methylthio)pyrimidine-2,4-diamine
Chemical Abstracts name 6-chloro-5-(methylthio)-2,4-pyrimidinediamine
CASRN[68925417] DevelopmentcodesUK-J 1506 (Produits Chimiques)
SmilescodeCSc1c(N)nc(N)nc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 190.6 M.f. C5H7ClN4S
COMMERCIALISATION:
History Herbicide discovered by Produits Chimiques Ugine Kuhlmann.
tioxymid
Fungicide
NOMENCLATURE:
Common name tioxymid (BSI, E-ISO); tioxymide ((m) F-ISO)
IUPACname 5-isothiocyanato-2-methoxy-N,N-dimethyl-m-toluamide
Chemical Abstracts name 5-isothiocyanato-2-methoxy-N,N,3-trimethylbenzamide
CASRN[70751949] DevelopmentcodesSAF-787; 710 352-S
SmilescodeCOc1c(C)cc(N=C=S)cc1C(=O)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C12H14N2O2S
COMMERCIALISATION:
History Fungicide introduced by Shionogi & Co., Ltd.
526 tioxymid
tolprocarb
Fungicide
C H3
O
NH
C H3
F OH
O C H3
N
F
NOMENCLATURE: F H
Common name tolprocarb (pa ISO)

IUPACname 2,2,2-trifluoroethyl (S)-[2-methyl-1-(p-toluoylaminomethyl)propyl]
carbamate
Chemical Abstracts name 2,2,2-trifluoroethyl N-[(1S)-2-methyl-1-[[(4-methylbenzoyl)
amino]methyl]propyl]carbamate CASRN[911499622] DevelopmentcodesMTF
0301 SmilescodeCc1ccc(cc1)C(=O)NC[C@H](C(C)C)/N=C(\O)/OCC(F)(F)F
N-m-tolylphthalamic acid
O CH3
C
NH
CO2H
NOMENCLATURE:
IUPACname N-m-tolylphthalamic acid
Other names N-m-t CASRN[85723] ECno2016269
SmilescodeCc1cccc(NC(=O)c2ccccc2C(=O)O)c1
PHYSICAL CHEMISTRY:
Mol. wt. 255.3 M.f. C15H13NO3 Form White powder. M.p.152C Solubility In water
0.1 g/l.
COMMERCIALISATION:
History Plant growth regulator.
Manufacturers Makhteshim-Agan
APPLICATIONS:
ModeofactionSystemic plant growth regulator which prevents abscission of flowers
and young fruit. Uses Increases fruit set of tomatoes, aubergines and lima beans under
N-m-tolylphthalamic acid 527

adverse conditions. Formulation types WP.

PRODUCTS:
Discontinued products Tomaset* (Makhteshim-Agan).
EU Status (1107/2009) Not approved (as tolylphtalam), Commission Regulation
2076/2002.
rabbits >20000 mg/kg. Inhalation LC50 for rats >5 mg/l.
tralopyril
Anti-foulant, molluscicide
N
Br
F
Cl N
H F
F
See also The Manual of Biocontrol Agents entry:
NOMENCLATURE:
Common name tralopyril (BSI, E-ISO, (m) F-ISO)
IUPACname 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Chemical Abstracts name 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-
pyrrole-3-carbonitrile CASRN[122454299] DevelopmentcodesAC303268
SmilescodeN#CC1=C(C2=CC=C(Cl)C=C2)NC(C(F)(F)F)=C1Br
PHYSICAL CHEMISTRY:
Mol. wt. 349.5 M.f. C12H5BrClF3N2
528 tralopyril
transpermethrin
Insecticide
O
CH2 O
H C O
Cl
C CH H
CH3 CH3
Cl
(1R)-trans- isomer (biopermethrin)
Cl
C CH H
O
Cl
H C CH2
CH3 CH3 O O
(1S)-trans- isomer
IRAC3
An isomer pair, component of permethrin.
NOMENCLATURE:
Common name transperm(thrine) ((f) F-ISO); transpermethrin (BSI, E-ISO)
IUPACname 3-phenoxybenzyl (1RS)-trans-3-(2,2-dichlorovinyl)-2,2-dimethyl
cyclopropanecarboxylate; 3-phenoxybenzyl (1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-
Chemical Abstracts name rel-(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; trans-()-(3-phenoxyphenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other names permethrin-G CASRN[61949777], formerly [52341329]; [51877
748] biopermethrin (the (1R)-trans- resolved isomer) (q.v.); [54774479] (1S)-trans-
isomer DevelopmentcodesNRDC 146; RU 22090
SmilescodeCC1(C)C(C=C(Cl)Cl)C1C(=O)OCc2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY:
Mol. wt. 391.3 M.f. C21H20Cl2O3
APPLICATIONS:
transpermethrin 529
ANALYSIS:
triamiphos
Acaricide, fungicide, insecticide
IRAC1B
NOMENCLATURE:
Common name triamiphos (BSI, E-ISO, (m) F-ISO)
IUPACname 5-amino-3-phenyl-1H-1,2,4-triazol-1-yl-N,N,N,N-tetramethylphosphonic
diamide
Chemical Abstracts name P-(5-amino-3-phenyl-1H-1,2,4-triazol-1-yl)-N,N,N,N-
tetramethylphosphonic diamide CASRN[1031476] DevelopmentcodesWP 155
(Philips-Duphar) SmilescodeCN(C)P(=O)(N(C)C)n1nc(nc1N)c2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 294.3 M.f. C12H19N6OP Form Colourless solid.
M.p.167168C; (tech., 166170C) Solubility In water 250 mg/l (20C). Moderately
to easily soluble in most organic solvents. Stability Stable at room temperature under
neutral or slightly alkaline conditions, but is readily hydrolysed by concentrated mineral
acids.
COMMERCIALISATION:
History Acaricide, fungicide and insecticide reported by B. G. van den Bos etal. (Rec. Trav.
Chim. Pays-Bas, 1960, 79, 807). Introduced by Philips-Duphar B.V. (later Uniroyal Chemical
Co., Inc.). Patents NL 109510, US 3121090,US 3220922.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionSystemic acaricide, fungicide and
insecticide. Uses For powdery mildew control, at 25 g/100 l on apples and roses. Also has
insecticidal and acaricidal properties.
PRODUCTS:
Discontinued products Wepsyn 155* (Philips-Duphar).
ANALYSIS:
Product and residue analysis is by the colorimetric determination of 5-phenyl-1,2,4-triazol-
3-ylamine formed on acid hydrolysis.
530 triamiphos
Oral Acute oral LD50 for rats 20 mg/kg. Toxicity Class WHO (a.i.) Ib ECClassification
T+; R27/28
triapenthenol
OH
CH CH
C C(CH3)3
N
N
N
NOMENCLATURE:
Common name triapenth(nol) ((m) F-ISO); triapenthenol (BSI, E-ISO)
IUPACname (E)-(RS)-1-cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Chemical Abstracts name (E)-()--(cyclohexylmethylene)--(1,1-dimethylethyl)-1H-
1,2,4-triazole-1-ethanol CASRN[76608883] (E)- isomer
DevelopmentcodesBAY RSW 0411
SmilescodeCC(C)(C)C(O)/C(=C/C1CCCCC1)/n2cncn2;
without stereochemistry: CC(C)(C)C(O)C(=CC1CCCCC1)n2cncn2
PHYSICAL CHEMISTRY:
Mol. wt. 263.4 M.f. C15H25N3O Form Colourless crystals. M.p.135.5C
V.p. 4.4 103 mPa (20C) Kow logP = 2.274 Solubility In water 68 mg/l. In acetone 150,
dichloromethane >200, hexane 510, methanol 433, isopropanol 100200, toluene 2050
(all in g/l).
COMMERCIALISATION:
History Plant growth regulator reported at 44th Deutsche Pflanzenschutz-Tag (1984),
K. Lrssen & W. Reiser (Proc. 1985 Br. Crop Prot. Conf. - Weeds, 1, 121). Introduced in
Belgium and France (1989) by Bayer AG.
APPLICATIONS:
Biochemistry The (S)-(-)- enantiomer is an inhibitor of gibberellin biosynthesis and
a plant growth regulator; the (R)-(+)- enantiomer inhibits sterol demethylation and is
fungicidal (K. Lrssen, Pflanz.-Nachr. Bayer (Eng. Ed.), 1988, 41, p. 306; U. Kraatz & L. Born,
ibid., p. 340). Uses Plant growth regulator used to control lodging in oilseed rape and
grasses grown for seed. (The (R)-(+)- enantiomer is fungicidal). Formulation types WG .
PRODUCTS:
Discontinued products Baronet* (Bayer).
triapenthenol 531
ANALYSIS:
Residues determined by glc with TID (R. Brennecke, Pflanz.-Nachr. Bayer (Engl. Ed.), 1990, 43,
159).
Oral Acute oral LD50 for rats >5000, micec.4000, dogsc.5000 mg/kg. Skin and eye Acute
percutaneous LD50 for rats >5000 mg/kg. NOEL (2 y) for rats 100 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD50 (14 d) for Japanese quail and hens >5000, for canaries (7 d)
>1000 mg/kg. Fish LC50 (96 h) for golden orfe 34.4, guppies 18.8, trout 37, and carp
18 mg/l. Daphnia LC50 (48 h) >70 mg a.i. (as 70% WP)/l. Bees Not harmful to honeybees.
triarathene
Acaricide
NOMENCLATURE:
Common name triarath(ne) ((m) F-ISO); triarathene (BSI, E-ISO, ANSI)
IUPACname 5-(4-chlorophenyl)-2,3-diphenylthiophene (I)
DevelopmentcodesUBI-T930 SmilescodeClc1ccc(cc1)c2cc(c(s2)c3ccccc3)c4ccccc4
PHYSICAL CHEMISTRY:
Mol. wt. 346.9 M.f. C22H15ClS Form Colourless crystalline solid. M.p.127C
B.p. 462C V.p. 1.3 106 mPa (25C) Kow logP = 8 Stability It is thermally stable at
127C; exposure to sunlight for several months causes a superficial yellowing.
COMMERCIALISATION:
History Acaricide reported by D. I. Relyea etal. (Proc. Int. Congr. Plant Prot., 10th, 1983, 1,
355). Evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
ModeofactionContact acaricide. Uses Acaricide effective at 280560 g/ha against
eriophyoid mites (Aculus cornutus, Epitrimerus pyri and Phyllocoptruta oleivora) and
at 2.26 kg/ha against Eutetranychus banksi, Panonychus ulmi and Tetranychus urticae. Its
acaricidal action depends on the presence of daylight. The relationship between chemical
structure and acaricidal activity has been discussed (D. I. Relyea et al., Proc. Int. Congr. Plant
Prot., 10th, 1983, 1, 355). Formulation types WP.
PRODUCTS:
Discontinued products Micromite* (Uniroyal).
532 triarathene
Oral Acute oral LD50 for rats >10000 mg tech./kg. Skin and eye Acute percutaneous
LD50 for rabbits >2000 mg/kg. Mild eye and no skin irritation (for the WP). Inhalation for
rats >5.1 mg/l.
ECOTOXICOLOGY:
Birds LC50 (8 d) for bobwhite quail and mallard duck >5620 mg/kg diet. Fish LC50 (96 h)
for bluegill and rainbow trout >100 mg/l. Daphnia LC50 (48 h) 64 mg/l.
triarimol
Fungicide
NOMENCLATURE:
Common name triarimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname 2,4-dichloro--(pyrimidin-5-yl)benzhydryl alcohol
Chemical Abstracts name -(2,4-dichlorophenyl)--phenyl-5-pyrimidinemethanol
CASRN[26766278] DevelopmentcodesEL 273
SmilescodeOC(c1ccccc1)(c2cncnc2)c3ccc(Cl)cc3Cl
PHYSICAL CHEMISTRY:
Mol. wt. 331.2 M.f. C17H12Cl2N2O
COMMERCIALISATION:
History Fungicide reported by J.V. Gramlich etal. (Proc. Br. Insectic. Fungic. Conf., 5th, 1969,
2, 576). Evaluated by Eli Lilly & Co.
PRODUCTS:
Discontinued products Trimidal* (Lilly).
triazbutil
Fungicide
NOMENCLATURE:
Common name triazbutil (BSI, E-ISO, (m) F-ISO, ANSI)
IUPACname 4-butyl-4H-1,2,4-triazole (I)
Chemical Abstracts name (I) Other names butrizol CASRN[16227104]
DevelopmentcodesRH-124 SmilescodeCCCCn1cnnc1
PHYSICAL CHEMISTRY:
Mol. wt. 125.2 M.f. C6H11N3
triazbutil 533
COMMERCIALISATION:
PRODUCTS:
Discontinued products Indar* (Rohm & Haas).
tributyl phosphorotrithioite
NOMENCLATURE:
IUPACname tributyl phosphorotrithioite (I)
Chemical Abstracts name (I) Other names merphos CASRN[150505]
SmilescodeCCCCSP(SCCCC)SCCCC
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 298.5 M.f. C12H27PS3 Form Colourless to pale
yellow liquid. B.p. 115134C /0.08 mmHg S.g./density 0.991.01 (20C)
Solubility Sparingly soluble in water; very soluble in most organic solvents.
COMMERCIALISATION:
History Introduced by the Mobil Chemical Co. and later by Rhne-Poulenc Agrochimie.
Patents US 2955803
APPLICATIONS: Uses At 1.22.5 kg/ha to defoliate cotton. Can induce leaf abscission
in some other plants, such as roses and hydrangeas. Formulation types AI.
PRODUCTS:
Discontinued products Folex* (Rhne-Poulenc Phytosanitaire).
ANALYSIS:
Product analysis by glc. Residues determined by glc with MCD.
Oral Acute oral LD50 for male albino rats 1272 mg/kg. Skin and eye Acute percutaneous
LD50 for albino rabbits >4600 mg/kg. NOEL In 90 d feeding trials, dogs and rats receiving
750 mg/kg diet showed depression of cholinesterase but no other effect on pathology or
histology. ADI/RfD (EPA) cRfD 0.00003 mg/kg b.w. [1991].
534 tributyl phosphorotrithioite

tricamba
Herbicide
NOMENCLATURE:
Common name tricamba (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPACname 3,5,6-trichloro-o-anisic acid
Chemical Abstracts name 2,3,5-trichloro-6-methoxybenzoic acid
CASRN[2307495] SmilescodeCOc1c(Cl)cc(Cl)c(Cl)c1C(=O)O
PHYSICAL CHEMISTRY:
Mol. wt. 255.5 M.f. C8H5Cl3O3
COMMERCIALISATION:
History Herbicide developed by Velsicol Corp. (later Sandoz AG).
PRODUCTS:
Discontinued products Banvel T* (Sandoz).
trichlamide
Fungicide
NOMENCLATURE:
Common name trichlamide (BSI, E-ISO, (m) F-ISO)
IUPACname (RS)-N-(1-butoxy-2,2,2-trichloroethyl)salicylamide
Chemical Abstracts name ()-N-(1-butoxy-2,2,2-trichloroethyl)-2-hydroxybenzamide
CASRN[70193214] DevelopmentcodesNK-483 (Nippon Kayaku)
SmilescodeCCCCOC(NC(=O)c1ccccc1O)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 340.6 M.f. C13H16Cl3NO3 Form Colourless
crystals. M.p.7374C V.p. <10 mPa (20C) Solubility In water 6.5 mg/l. Soluble in
acetone, alcohols, and benzene. Stability Stable 70C, and stable to light.
COMMERCIALISATION:
History Fungicide reported by T. Ohmori etal. (Plant Dis., 1986, 70, 51). Introduced in
Japan (1985) by Nippon Kayaku Co., Ltd. Patents GB 2004540; DE 2837819; US 4200632
APPLICATIONS:
ModeofactionNon-systemic soil fungicide. Uses Control of diseases caused by
Aphanomyces and Streptomyces spp., and related fungal diseases (e.g. club root, Root rots,
scab, etc.) in potatoes and vegetables. Formulation types DP .
PRODUCTS:
Discontinued products Hataclean* (Nippon Kayaku).
trichlamide 535
ANALYSIS:
LD50 for rats and mice >5000 mg/kg. Non-irritating to eyes and skin (rabbits).
NOEL (2 y) for male rats 0.361 mg/kg, female rats 0.431 mg/kg daily. (2 y, gavage) for male
dogs 10 mg/kg daily, for female dogs 2 mg/kg daily. Non-teratogenic in rats and rabbits.
Other Acute i.p. LD50 for male rats 1.54, female rats 1.14, male mice 1.59, female mice
1.66 mg/kg. Non-mutagenic in the Ames test, chromosomal aberration test, and
micronucleus test (K. Fukunaga Jpn. Pestic. Inf. 1990, 56, 1214).
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 6090 d.
2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
Insecticide
NOMENCLATURE:
IUPACname 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
Chemical Abstracts name 3,4-dichloro--(trichloromethyl)benzenemethyl
acetate Other names benzethazet*; plifenate* (rejected common name proposals)
CASRN[21757824] DevelopmentcodesBAY MEB 6046
SmilescodeCC(=O)OC(c1ccc(Cl)c(Cl)c1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 336.4 M.f. C10H7Cl5O2 Form Colourless crystalline solid. M.p.84.5C
V.p. 0.014 mPa (20C) Henry 9.42 105 Pa m3 mol1 (calc.) Solubility In water 50 mg/
kg (20C). In cyclohexanone >600, isopropanol <10 (both in g/kg, 20C).
COMMERCIALISATION:
History Insecticide reported by W. Behrenz etal. (Pflanz.-Nachr. Bayer (Engl. Ed.), 1977, 30,
237). Introduced by Bayer AG. Patents DE 2110056
APPLICATIONS:
Biochemistry The (-)- isomer is more active. ModeofactionContact insecticide with
respiratory action and long residual activity. Uses It was recommended for use against
such pests as clothes moths, flies and mosquitoes. Formulation types AE; DP; UL .
PRODUCTS:
Discontinued products Baygon MEB* (Bayer); Penfenate* (Bayer).
536
2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
ANALYSIS:
Product and residue analysis by glc with ECD.
rats >1000 mg/kg. Inhalation (4 h) for rats >0.7 mg/l air. NOEL (90 d) for rats
1000 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD50 for hens >2500 mg/kg. Fish LC50 (96 h) for orfe 0.51.0 mg/l.
ENVIRONMENTAL FATE:
Animals Following oral adminstration, there is no concentration in adipose tissue or liver,
kidney or brain. The alcohol has been isolated as a metabolite in animal tissue (W. Behrenz
et al., Pflanz.-Nachr. Bayer 1977, 30, 237).
4,5,7-trichloro-2,1,3-benzothiadiazole
Herbicide
NOMENCLATURE:
IUPACname 4,5,7-trichloro-2,1,3-benzothiadiazole (I)
Chemical Abstracts name (I) CASRN[1982554] DevelopmentcodesPH 4021
SmilescodeClc1cc(Cl)c2nsnc2c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 239.5 M.f. C6HCl3N2S
COMMERCIALISATION:
History Herbicide reported by J. Dams etal. (Proc. Br.Weed Control Conf., 7th, 1964, p.
1091). Evaluated by Philips-Duphar B.V. (later Uniroyal Chemical Co., Inc.).
trichlorobenzyl chloride
Herbicide
NOMENCLATURE:
IUPACname trichlorobenzyl chloride
Chemical Abstracts name trichloro(chloromethyl)benzene Other names TCBC
CASRN[1344327], formerly [25429361] SmilescodeClCc1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 229.9 M.f. C7H4Cl4
COMMERCIALISATION:
History Herbicide introduced by Monsanto Co.
trichlorobenzyl chloride 537

PRODUCTS:
Discontinuedmixtures Randox-T* (+allidochlor) (Monsanto).
trichloronat
Insecticide
IRAC1B
NOMENCLATURE:
Common name trichloronate (BSI (before 1984), France); trichloronat (BSI (since 1984),
E-ISO, (m) F-ISO)
IUPACname O-ethyl O-2,4,5-trichlorophenyl ethylphosphonothioate
Chemical Abstracts name O-ethyl O-(2,4,5-trichlorophenyl) ethylphosphonothioate
CASRN[327980] ECno2063261 DevelopmentcodesBayer 37 289; S 4400
SmilescodeCCOP(=S)(CC)Oc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 333.6 M.f. C10H12Cl3O2PS Form Amber-coloured liquid. B.p. 108C /0.01
mmHg V.p. 2 mPa (20C) Henry 1.33 10-2 Pa m3 mol1 (calc.) S.g./density 1.365
(20C) Solubility In water 50 mg/l (20C). In dichloromethane, isopropanol >1.2 kg/kg
(20C). Stability Hydrolysed by alkali.
COMMERCIALISATION:
History Insecticide reported by R. O. Drummond (J. Econ. Entomol., 1963, 56, 831).
Introduced by Bayer AG. Patents DE 1099530
APPLICATIONS:
Uses It was recommended for the control of root maggots, other soil-dwelling insects and
wireworms. Formulation types EC; GR; Seed treatment.
PRODUCTS:
Discontinued products Agrisil* (Bayer); Agritox* (Bayer); Phytosol* (Bayer).
ANALYSIS:
Product analysis by uv spectroscopy after hydrolysis to 2,4,5-trichlorophenol. Residues
determined by glc (E. Mllhoff, Pflanz.-Nachr. Bayer (Engl. Ed.), 1968, 21, 331). See also Pestic.
Anal. Man., I, 302.
Oral Acute oral LD50 for rats 1637.5, rabbits 2550 mg/kg. Skin and eye Acute
percutaneous LD50 for male rats 135341 mg/kg. NOEL In 2 y feeding trials, rats receiving
3 mg/kg diet showed no symptom of poisoning. ADI/RfD (JMPR) No ADI [1971].
Toxicity Class WHO (a.i.) Ia ECClassification T+; R28| T; R24| N; R50, R53
538 trichloronat
triclopyricarb
Fungicide
OH
CH CH
C C(CH3)3
N
N
N
NOMENCLATURE:
Common name triclopyricarb (pa ISO)
IUPACname methyl N-methoxy-2-(3,5,6-trichloro-2-pyridyloxymethyl)carbanilate
Chemical Abstracts name methyl N-methoxy-N-[2-[[(3,5,6-trichloropyridin-2-yl)oxy]
methyl]phenyl]carbamate CASRN[902760401] DevelopmentcodesSYP7017
SmilescodeCOC(=O)N(c1ccccc1COc2c(cc(c(n2)Cl)Cl)Cl)OC
PHYSICAL CHEMISTRY:
Mol. wt. 391.63 M.f. C15H13Cl3N2O4
tridiphane
Herbicide
NOMENCLATURE:
Common name tridiphane (BSI, ANSI, E-ISO)
IUPACname (RS)-2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane
Chemical Abstracts name ()-2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane
SmilescodeClc1cc(Cl)cc(c1)C2(CC(Cl)(Cl)Cl)CO2
PHYSICAL CHEMISTRY:
Mol. wt. 320.4 M.f. C10H7Cl5O Form Colourless crystals. M.p.42.8C V.p. 29 mPa
(25C) Kow logP = 4.34 Henry 5.16 Pa m3 mol1 (calc.) Solubility In water 1.8 mg/l
(25C). In methanol 0.98, acetone 9.1, xylene 4.6, chlorobenzene 5.6, dichloromethane 7.1
(all in kg/kg, 25C). Stability Hydrolysis DT50 80 d (pH 59, 35C) (ARS PPD).
F.p. 46.7C
COMMERCIALISATION:
History Herbicide reported by E. S. Saunders etal. (Proc. North Cent.Weed Control Conf.,
1981, p. 133). Introduced by Dow Chemical Co. (later DowElanco).
Patents US 4211549; EP 81351
tridiphane 539
APPLICATIONS:
ModeofactionSelective non-systemic herbicide, absorbed by the leaves and roots.
Uses Control of annual grass seedlings and broad-leaved weeds in maize. Applied post-
emergence in combination with triazine herbicides. Formulation types EC.
PRODUCTS:
Discontinued products Nelpon* (DowElanco); Tandem* (DowElanco).
ANALYSIS:
Product analysis by hplc. Residues determined by glc/ECD (Pestic. Anal. Man., II, 180.424;
Resid. Anal. Methods).
LD50 for rabbits 3536 mg/kg. Moderately irritating to eyes and skin (rabbits). Potential
skin sensitiser. NOEL (2 y) for rats 3 mg/kg daily. ADI/RfD (EPA) cRfD 0.003 mg/kg b.w.
[1992]. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD50 for mallard ducks >2510 mg/kg. Dietary LC50 (8 d) for mallard
ducks and bobwhite quail 5620 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.53, bluegill
sunfish 0.37 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT50 (ave.) 26 d, under aerobic conditions.
trifenmorph
Molluscicide
NOMENCLATURE:
Common name trifenmorph (BSI, E-ISO); triphenmorphe ((m) F-ISO)
IUPACname 4-tritylmorpholine
Chemical Abstracts name 4-(triphenylmethyl)morpholine CASRN[1420060]
ECno2158122 DevelopmentcodesWL 8008 (Shell)
SmilescodeC1CN(CCO1)C(c2ccccc2)(c3ccccc3)c4ccccc4
PHYSICAL CHEMISTRY:
Composition Tech. is 9095%. Mol. wt. 329.4 M.f. C23H23NO Form Colourless
crystalline solid. M.p.176178C, resolidifying and remelting at 185187C; (tech. melts
150170C, and again at 170185C) V.p. 1.9 10-2 mPa (20C)
Henry 3.13 101 Pa m3 mol1 (calc.) Solubility In water 0.02 mg/l (20C). In carbon
tetrachloride 300, chloroform 450, tetrachloroethylene 255 (all in g/l, 20C). Stability
Stable to heat and alkali, but hydrolysed by mild acid to morpholine and triphenylmethanol.
Slight decomposition occurs in uv light.
540 trifenmorph
COMMERCIALISATION:
History Molluscicide reported by C. B. C. Boyce etal. (Nature (London), 1966, 210, 1140).
Introduced by Shell Research Ltd.
APPLICATIONS: Uses Effective against aquatic and semi-aquatic snails. Recommended
for application to irrigation and other moving water systems, at 0.030.01 mg/l, and in
static water atc.1.02.0 mg/l. Also recommmended for application to Lymnaea truncatula
habitats, at 500 g/ha, to control fascioliasis.
PRODUCTS:
Discontinued products Frescon* (Shell).
ANALYSIS:
Product analysis is by non-aqueous titration with a perchloric-acetic acid mixture
(Pesticides used in Public Health, p. 248) or by hplc. Residues may be determined
colorimetrically with cyclohaxane-sulfuric acid (K. I. Beynon & G. R. Thomas, Bull, WHO,
1967, 37, 47); a method suitable for use under field conditions is available (K. I. Beynon & A.
N. Wright, Pestic. Sci., 1975, 6, 515).
PDS 64 (1985). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD50 for rats 4462200, mice 7004800 mg/kg. Toxicity Class WHO
(a.i.) III ECClassification Xn; R22| N; R50, R53
ENVIRONMENTAL FATE:
Plants In plants, and in soil and water, broken down initially to triphenylmethanol (K. I.
Beynon, et al., Pestic. Sci., 1972, 3, 689). Soil/Environment See plants.
trifenofos
IRAC1B
NOMENCLATURE:
Common name trifenofos (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname O-ethyl S-propyl O-2,4,6-trichlorophenyl phosphorothioate
Chemical Abstracts name O-ethyl S-propyl O-(2,4,6-trichlorophenyl)
phosphorothioate CASRN[38524822] DevelopmentcodesRH-218; RH-8218
SmilescodeCCCSP(=O)(OCC)Oc1c(Cl)cc(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 363.6 M.f. C11H14Cl3O3PS
COMMERCIALISATION:
History Acaricide and insecticide introduced by Rohm & Haas Co.
trifenofos 541
APPLICATIONS:
trifop; trifop-methyl
Herbicide
NOMENCLATURE:
Common name trifop (BSI, E-ISO, (m) F-ISO)
IUPACname (RS)-2-[4-(,,-trifluoro-p-tolyloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoic
acid CASRN[58594744] trifop (unstated stereochemistry); [59011302] trifop
(racemate); [58594777] trifop-methyl (unstated stereochemistry); [59011335] trifop-
methyl (racemate) DevelopmentcodesHoe 29 152 (trifop-methyl)
PHYSICAL CHEMISTRY:
Mol. wt. 326.3; (methyl ester 340.3) M.f. C16H13F3O4; (methyl ester C17H15F3O4)
COMMERCIALISATION:
trifopsime
Herbicide
NOMENCLATURE:
Common name trifopsime (BSI, E-ISO, (f) F-ISO)
IUPACname acetone (R)-O-[2-[4-(,,-trifluoro-p-tolyloxy)phenoxy]propionyl]oxime
Chemical Abstracts name (R)-2-propanone O-[1-oxo-2-[4-[4-(trifluoromethyl)
phenoxy]phenoxy]propyl]oxime CASRN[72131761]
DevelopmentcodesRo 138895
SmilescodeCC(Oc1ccc(Oc2ccc(cc2)C(F)(F)F)cc1)C(=O)ON=C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 381.4 M.f. C19H18F3NO4
COMMERCIALISATION:
History Herbicide evaluated by Hofmann-La Roche Ltd.
542 trifopsime
trimethacarb
Insecticide, molluscicide
CH3 CH3
CH3 OCONHCH3 OCONHCH3
CH3 CH3 CH3
3,4,5- isomer 2,3,5- isomer

IRAC1A; carbamate
NOMENCLATURE:
Common name trimethacarb (BSI, ANSI, E-ISO)
IUPACname Reaction product comprising 3,4,5-trimethylphenyl methylcarbamate (I)
and 2,3,5-trimethylphenyl methylcarbamate (II) in a ratio between 3.5:1 and 5.0:1 m/m
Chemical Abstracts name 2,3,5(or 3,4,5)-trimethylphenyl methylcarbamate
CASRN[12407862] trimethacarb; [2686999] (I); [2655154] (II)
DevelopmentcodesUC 27 867 (Union Carbide); SD 8530 (Shell) Official codes OMS 597
Smilescode2,3,5-isomer:CNC(=O)Oc1cc(C)cc(C)c1C;3,4,5-isomer:CNC(=O)
Oc1cc(C)c(C)c(C)c1
PHYSICAL CHEMISTRY:
Mol. wt. 193.2 M.f. C11H15NO2 Form Buff to brown, crystalline solid. M.p.105114C
V.p. 6.8 mPa (25C) Henry 2.27 10-2 Pa m3 mol1 (calc.) Solubility In water >58 mg/
kg (23C). Not readily soluble in organic solvents. Stability Decomposed by strong acids
and alkalis. Stable to light.
COMMERCIALISATION:
History Insecticide originally introduced by Shell Development Co. (now E. I. du Pont
de Nemours & Co.) and later by Union Carbide Agrochemicals (now Bayer AG, who no
longer manufacture or market it).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor ModeofactionInsecticide with predominantly
stomach action, but also some contact action. Long residual activity. Uses Control of
corn rootworms larvae in maize. Also controls a wide range of insect and mollusc pests,
and acts as a mammal and bird repellent. Phytotoxicity Non-phytotoxic when used as
directed. Phytotoxic to the seeds of some crops, including maize, sorghum, wheat and rice.
PRODUCTS:
Discontinued products Broot* (Drexel); Landrin* (Shell).
trimethacarb 543
ANALYSIS:
Residues by glc with ECD (S. C. Lau & R. L. Marxmiller, J. Agric. Food Chem., 1970, 18,
413415). See also Pestic. Anal. Man., II, 180.305. In soil by gc/NPD (Environ. Chem. Methods).
>2000 mg/kg. NOEL (2 y) for rats 50 ppm (2.5 mg/kg b.w.) (EPA Tracking).
ADI/RfD (EPA) 0.0025 mg/kg b.w. [1986]. Toxicity Class WHO (a.i.) O.
ECOTOXICOLOGY:
Fish Toxic to fish. Bees Toxic to bees, in spray formulations.
ENVIRONMENTAL FATE:
Insecticides). Plants In plants, metabolism occurs via hydroxylation of the N-methyl group
and at the 3- and 4-methyl positions. All metabolites may be conjugated as glucosides.
Soil/Environment Soil DT50c.60 d in sterile soil.
trimeturon
Herbicide
NOMENCLATURE:
Common name trimeturon (BSI, (m) France)
IUPACname 3-(4-chlorophenyl)-1,1,2-trimethylisourea
Chemical Abstracts name methyl N-(4-chlorophenyl)-N,N-
dimethylcarbamimidate CASRN[3050279] DevelopmentcodesBAY 40 557
SmilescodeCOC(=Nc1ccc(Cl)cc1)N(C)C
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
triprene
Insecticide
NOMENCLATURE:
Common name triprene (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPACname S-ethyl (E,E)-(RS)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate
544 triprene
Chemical Abstracts name (2E,4E)-S-ethyl 11-methoxy-3,7,11-trimethyl-

2,4-dodecadienethioate CASRN[40596803], formerly [53023544]
DevelopmentcodesZR 619
SmilescodeCCSC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC
PHYSICAL CHEMISTRY:
Mol. wt. 312.5 M.f. C18H32O2S
COMMERCIALISATION:
History Insect growth regulator introduced by Zoecon Corp. (later Sandoz AG).
APPLICATIONS:
ModeofactionInsect growth regulator.
PRODUCTS:
Discontinued products Altorick* (Sandoz).
tripropindan
Herbicide
NOMENCLATURE:
Common name tripropindan (BSI, E-ISO); tripropindane ((m) F-ISO)
IUPACname 1-(6-isopropyl-1,1,4-trimethylindan-5-yl)propan-1-one
Chemical Abstracts name 1-[2,3-dihydro-1,1,4-trimethyl-6-(1-methylethyl)-1H-
inden-5-yl]-1-propanone CASRN[6682775] DevelopmentcodesRo 70668
SmilescodeCC(C)c1cc2c(CCC2(C)C)c(C)c1CC(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 258.4 M.f. C18H26O
COMMERCIALISATION:
History Herbicide evaluated by Roche.
tritac
Herbicide
NOMENCLATURE:
Common name tritac (WSSA)
IUPACname 1-(2,3,6-trichlorobenzyloxy)propan-2-ol
Chemical Abstracts name 1-[(2,3,6-trichlorophenyl)methoxy]-2-propanol
CASRN[1861445] SmilescodeCC(O)COCc1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 269.6 M.f. C10H11Cl3O2
tritac 545
COMMERCIALISATION:
History Herbicide introduced by Hooker Chemical Corp.
PRODUCTS:
Discontinued products Tritac* (Hooker).
UBI-S734
Herbicide
NOMENCLATURE:
IUPACname 2-pyridyl 1-(2,5-xylyl)ethyl sulfone 1-oxide
Chemical Abstracts name 2-[[1-(2,5-dimethylphenyl)ethyl]sulfonyl]pyridine 1-oxide
CASRN[60263889] DevelopmentcodesUBI-S734
SmilescodeCC(c1cc(C)ccc1C)S(=O)(=O)c2cccc[n+]2[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 291.4 M.f. C15H17NO3S
COMMERCIALISATION:
History Herbicide evaluated by Uniroyal Chemical Co., Inc.
urbacid
Fungicide
NOMENCLATURE:
Common name urbacid (JMAF)
IUPACname methylarsinediyl bis(dimethyldithiocarbamate)
Chemical Abstracts name dimethylcarbamodithioic acid bis(anhydrosulfide) with
methylarsonodithious acid CASRN[2445070]
SmilescodeCN(C)C(=S)S[As](C)SC(=S)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 330.4 M.f. C7H15AsN2S4 Form Colourless crystals. M.p.144C V.p. Low
volatility Solubility Insoluble in water. Soluble in most organic solvents.
COMMERCIALISATION:
History Fungicide introduced by Bayer AG. Patents US 2644005; DE 833271
APPLICATIONS:
ModeofactionProtective fungicide. Uses Sprays were used at 240480 g a.i. (as 800 g/
kg WP)/ha. It showed promise against Venturia inaequalis on apples, and was mainly used as
a mixture with thiram and ziram. Formulation types WP.
546 urbacid
PRODUCTS:
Discontinued products Monzet* (Bayer); Urbacid* (Bayer);
Discontinuedmixtures Tuzet* (+thiram +ziram) (Bayer).
ANALYSIS:
Product analysis was by a titrimetric method. Residues may be determined by a
colorimetric method after conversion to arsenate (H. Frehse & H.Tietz, J. Agric. Food Chem.,
1959, 7, 553).
Oral Acute oral LD50 for rats 175 mg/kg. ECClassification Not specified, but
arsenic compounds in general (with exceptions) are assigned T; R23/25| N; R50, R53
(concentration-dependent)
vamidothion
O
O S CH2 P(OCH3)2
C CH CH2 S
CH3NH CH3
NOMENCLATURE:
Common name vamidothion (BSI, E-ISO, (m) F-ISO, JMAF)
IUPACname O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate;
2-(2-dimethoxyphosphinoylthioethylthio)-N-methylpropionamide
Chemical Abstracts name O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-
oxoethyl]thio]ethyl] phosphorothioate CASRN[2275232] ECno2188948
Developmentcodes10 465 RP (Rhne-Poulenc); NPH 83 Official codes ENT 26 613
SmilescodeCNC(=O)C(C)SCCSP(=O)(OC)OC
PHYSICAL CHEMISTRY:
Mol. wt. 287.3 M.f. C8H18NO4PS2 Form Colourless needles; (tech., white, waxy solid).
M.p.c. 43C; (tech., 40C) V.p. Negligible (20C) Solubility Readily soluble in water
(4 kg/l), benzene, toluene, methyl ethyl ketone, ethyl acetate, acetonitrile, dichloromethane,
cyclohexanone, chloroform (allc.1 kg/l). Almost insoluble in cyclohexane and petroleum
ether. Stability Undergoes slight decomposition at room temperature, but solutions in
organic solvents (methyl ethyl ketone, cyclohexanone) are stable. Decomposed in strong
acidic or alkaline media.
vamidothion 547
COMMERCIALISATION:
History Insecticide reported by J. Desmoras etal. (Phytiatr.-Phytopharm., 1962, 11, 107).
Introduced by Rhne-Poulenc Agrochimie (later Bayer AG). Patents GB 872823; BE
575106 Manufacturers Bayer CropScience
APPLICATIONS:
acaricide. Metabolised in plants to the corresponding sulfoxide, which is of similar activity
to vamidothion but of greater persistence. Uses Systemic insecticide giving persistent
control of Eriosoma lanigerum and other piercing and sucking Homoptera in cotton, hops,
pome and stone fruit, and rice, at 3750 g/hl. Formulation types EC.
PRODUCTS:
Discontinued products Asystin Z* (Kwizda); Kilval* (Bayer CropScience); Kilvar*
(Japan) (Bayer CropScience); Trucidor* (Rhne-Poulenc); Vamidoate* (Rhne-Poulenc).
ANALYSIS:
Product analysis by hplc or glc (J. Desmoras et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 479). Residues determined by glc (idem, ibid.; Man. Pestic. Residue Anal., pp. 3, 6, 13;
Anal. Methods Residues Pestic., 1988, Part I, M2, M5, M10; A. Ambrus et al., J. Assoc. Off. Anal.
Chem., 1981, 64, 733; A. R. C. Hill, Analyst (London), 1984, 109, 483).
JMPR Evaln. I 66 (1992); JMPR Evaln. II 55 (1988). ICSC.758 (2001).
Oral Acute oral LD50 for male rats 100105, female rats 6467, mice 3437 mg/kg. For
the sulfoxide, acute oral LD50 for male rats 160, mice 80 mg/kg. Skin and eye Acute
percutaneous LD50 for mice 1460, rabbits 1160 mg/kg. Inhalation LC50 (4 h) for rats
1.73 mg/l air. NOEL In 90 d feeding trials, the growth rate of rats receiving 50 mg
vamidothion/kg diet or 100 mg of its sulfoxide/kg diet was unaffected. ADI/RfD (JMPR)
0.008 mg/kg b.w. [1988]. Toxicity Class WHO (a.i.) Ib ECClassification T; R25| Xn;
R21| N; R50
ECOTOXICOLOGY:
Birds Acute oral LD50 for pheasants 35 mg/kg. Fish LC50 (96 h) for zebra fish 590 mg/l. At
10 mg/l, harmless to goldfish (14 d). Daphnia EC50 (48 h) 0.19 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Oxidised to the sulfoxide and sulfone, followed by cleavage of the P-S and
S-C bonds, to give water-soluble metabolites. Plants Metabolised in plants to the
corresponding sulfoxide, which appears within hours after treatment. Also demethylation
and hydrolysis to phosphoric acid. After 20 days, all the toxic residues in the plant are in
the form of the sulfoxide. Soil/Environment In soil, DT50 1.01.5 d (aerobic, 22C).
548 vamidothion
vaniliprole
CF3
HO
Cl
CH3O C N Cl
N
H N
CF3S
CN
NOMENCLATURE:
Common name vaniliprole (BSI, E-ISO, (m) F-ISO, not Denmark)
IUPACname (E)-1-(2,6-dichloro-,,-trifluoro-p-tolyl)-5-(4-hydroxy-3-
methoxybenzylidenamino)-4-trifluoromethylthiopyrazole-3-carbonitrile
Chemical Abstracts name 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[[(E)-(4-
hydroxy-3-methoxyphenyl)methylene]amino]-4-[(trifluoromethyl)thio]-1H-pyrazole-
3-carbonitrile CASRN[145767971] DevelopmentcodesRPA-098231 (Rhne-
Poulenc)
PHYSICAL CHEMISTRY:
Mol. wt. 555.3 M.f. C20H10Cl2F6N4O2S
COMMERCIALISATION:
APPLICATIONS: Uses Foliar insecticide and acaricide for use in cotton, vines,
vegetables etc.
PRODUCTS:
Discontinued products Evaluation* (Aventis).
vernolate
Herbicide
CH3(CH2)2 S CH2CH2CH3
N C
CH3(CH2)2 O
NOMENCLATURE:
Common name vernolate (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPACname S-propyl dipropylthiocarbamate
Chemical Abstracts name S-propyl dipropylcarbamothioate CASRN[1929777]
vernolate 549
ECno2176817 DevelopmentcodesR-1607 (Stauffer)

SmilescodeCCCSC(=O)N(CCC)CCC
PHYSICAL CHEMISTRY:
Composition Tech. material is 95% pure. Mol. wt. 203.3 M.f. C10H21NOS
Form Clear liquid, with slight aromatic odour; (tech. is a clear yellow liquid). B.p. 150C
/30 mmHg V.p. 1.39 Pa (25C) Kow logP = 3.84 (20C) S.g./density 0.952 g/ml (20C)
Solubility In water 90 mg/l (20C). Miscible with common organic solvents, e.g. xylene,
methyl isobutyl ketone, kerosene, acetone, ethanol. Stability Stable in neutral media, and
relatively stable in acidic and alkaline media; DT50 13 d (pH 7, 40C). Stable up to 200C.
Decomposed by sunlight. F.p. 121C
COMMERCIALISATION:
History Herbicide introduced by Stauffer Chemical Co. (became Zeneca Agrochemicals).
First registered in USA in 1964. Patents US 2913327
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). ModeofactionSelective
herbicide, absorbed by the roots, with translocation to the stems and leaves. Germination
inhibitor. Uses Control of germinating broad-leaved and grass weeds in peanuts, soya
beans, maize, tobacco and sweet potatoes, at 1.53.0 kg/ha. Soil incorporation is necessary,
either pre-planting or pre-emergence. Formulation types EC; GR .
PRODUCTS:
Discontinued products Reward* (Zeneca); Saverit* (Chemolimpex); Savirox*
(Chemolimpex); Vernam* (Drexel).
ANALYSIS:
Product analysis by glc with FID (AOACMethods, 18th Ed., 974.05; CIPACHandbook, 1983,
1B, 1905); see also method for butylate, (ibid., 1983, 1B, 1744). Residues in crops and soils
determined by glc or by colorimetry after conversion to a derivative (G. G. Patchett & G.
H. Batchelder, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 337; W. J. Ja, Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 708). See also Pestic. Anal. Man., II, 180.240. In soil,
also by gc/NPD (Environ. Chem. Methods). In drinking water by glc with NPD (AOACMethods,
18th Ed., 991.07).
percutaneous LD50 for rabbits >5000 mg/kg. Non-irritating to eyes and skin (rabbits). Not
a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5 mg/l. NOEL NOAEL (2
generation) for rats 1 mg/kg b.w. (EPA RED); NOEL (90 d) for rats 32 mg/kg, for dogs 38
mg/kg daily. ADI/RfD (EPA) cRfD 0.001 mg/kg b.w. [1992, 1999, 2004]. Toxicity Class
WHO (a.i.) II EPA (formulation) III ECClassification Xn; R22| N; R51, R53
550 vernolate
ECOTOXICOLOGY:
Birds Dietary LC50 (7 d) for bobwhite quail 12000 mg/kg. Fish LC50 (96 h) for rainbow
trout 4.6, bluegill sunfish 8.4 mg/l. Bees Non-toxic to bees at 0.011 mg/bee.
ENVIRONMENTAL FATE:
Plants Readily metabolised by plants to CO2 and naturally-occurring plant constituents.
Soil/Environment In soil, microbial decomposition to mercaptan, amine, isopropanol and
CO2. DT50 (27C) 816 d; (4C) >64 d.
WL 108 477
Insecticide
IRAC4A
NOMENCLATURE:
IUPACname 2-nitromethylene-1,3-thiazinan-3-ylcarbamaldehyde
Chemical Abstracts name dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-
carboxaldehyde CASRN[94050507] DevelopmentcodesWL 108 477
PHYSICAL CHEMISTRY:
Mol. wt. 188.2 M.f. C6H8N2O3S Form Pale yellow crystals. M.p.138140C (decomp.).
Kow logP = 0.23 Solubility In water 500 mg/l (20C). In xylene 2.5 g/l.
COMMERCIALISATION:
History Insecticide reported by M. Harris etal. (Proc. 1986 Brit. Crop Prot. Conf. - Pests
Dis., 1, 115). Introduced by Shell Research Limited (became American Cyanamid Co.).
Manufacturers Cyanamid
APPLICATIONS:
Biochemistry Neurotoxic insecticide.
Oral Acute oral LD50 for mice 10002500 mg/kg. Skin and eye Acute percutaneous LD50
for mice >600 mg/kg.
ECOTOXICOLOGY:
Fish LD50 (96 h) for rainbow trout >100 mg/l.
WL 9385
Herbicide
NOMENCLATURE:
IUPACname 2-azido-4-tert-butylamino-6-ethylamino-1,3,5-triazine; 6-azido-N2-tert-
butyl-N4-ethyl-1,3,5-triazine-2,4-diamine
WL 9385 551
Chemical Abstracts name 6-azido-N-(1,1-dimethylethyl)-N-ethyl-1,3,5-

triazine-2,4-diamine CASRN[2854708] DevelopmentcodesWL 9385
SmilescodeCCNc1nc(NC(C)(C)C)nc([N-][N+]#N)n1
PHYSICAL CHEMISTRY:
Mol. wt. 236.3 M.f. C9H16N8
COMMERCIALISATION:
History Herbicide reported by R. A. Abbott & G. E. Barnsley (J. Sci. Food Agric., 1968, 19, 16).
Evaluated by Shell Research Ltd.
XMC
Insecticide
OCONHCH3
CH3 CH3
IRAC1A; carbamate
NOMENCLATURE:
Common name XMC (JMAF)
IUPACname 3,5-xylyl methylcarbamate
Chemical Abstracts name 3,5-dimethylphenyl methylcarbamate CASRN[2655143]
DevelopmentcodesH-69 (Hodogaya) SmilescodeCNC(=O)Oc1cc(C)cc(C)c1
PHYSICAL CHEMISTRY:
Composition Tech. grade is 97% pure. Mol. wt. 179.2 M.f. C10H13NO2 Form Colourless
crystals. M.p.99C (tech.) B.p. 239.7C V.p. 6.88 mPa (25C) Kow logP = 2.3 (25C)
Henry 2.33 103 Pa m3 mol1 (25C, calc.) S.g./density 1.16 (20C) Solubility In
water 0.53 g/l (25C). Soluble in most organic solvents; e.g. in acetone and ethanol >100,
xylene 67 (all in g/l, 25C); also soluble in cyclohexanone and 3,5,5-trimethylcyclohex-
2-enone. Stability Rapidly hydrolysed in alkaline media. Relatively stable to neutral and
weakly acidic aqueous solutions. Stable to light and to temperatures up to 90C.
COMMERCIALISATION:
History Introduced in 1968 as an insecticide by Hokko Chemical Industry Co., Ltd and
Hodogaya Chemical Co., Ltd.
Manufacturers Hodogaya; Saeryung
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. ModeofactionInsecticide with predominantly
contact action. Uses Control of leafhoppers and planthoppers on rice, and tea green
leafhoppers on tea, at 6001200 g/ha. Formulation types DP; EC; MG; WP.
552 XMC
PRODUCTS:
Discontinued products Cosban* (Hodogaya); Macbal* (Hodogaya); Maqbal*
(Hodogaya).
ANALYSIS:
Product analysis by hydrolysis to 3,5-xylenol, which is measured by uv spectroscopy.
Residues determined by hydrolysis to 3,5-xylenol, a derivative of which is measured by glc.
EU Status (1107/2009) Never notified to the EU.
Oral Acute oral LD50 for rats 542, rabbits 445, mice 245 mg/kg. Skin and eye Not a
skin irritant (rabbits). Inhalation LC50 for rats 1.02 mg/l. NOEL (90 d) for rats and mice
230 mg/kg b.w. daily. ADI/RfD 0.0034 mg/kg b.w. Toxicity Class WHO (a.i.) III EPA
(formulation) III ECClassification Xn; R22
ECOTOXICOLOGY:
Birds LD50 (14 d) for quail 188, mallard ducks 1637 mg/kg. Fish LC50 (48 h) for carp
>40 mg/l. Daphnia EC50 (3 h) for Daphnia pulex 0.055 mg/l. Algae EC50 (72 h) 12.3 mg/l.
Bees LD50 (48 h, oral) 0.095 g/bee; (48 h, contact) 0.53 g/bee. Worms LD50 (14 d)
45.4 mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals In insects, metabolism mainly involves hydroxylation of the benzene ring and
the ring methyl substituents. Soil/Environment In soil, hydrolysed to 3,5-xylenol and
N-methylcarbamic acid.
XRD-563
Fungicide
Cl CF3
NH
CH2
Cl O
NOMENCLATURE:
IUPACname 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide
Chemical Abstracts name 2,6-dichloro-N-[[4-(trifluoromethyl)phenyl]
methyl]benzamide CASRN[124426499] DevelopmentcodesXRD-563
SmilescodeFC(F)(F)c1ccc(CNC(=O)c2c(Cl)cccc2Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 348.2 M.f. C15H10Cl2F3NO Solubility In water 3.5
mg/l. Readily soluble in organic solvents, e.g. methanol and acetone.
XRD-563 553
COMMERCIALISATION:
History Reported by W. Arnold etal. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 443).
Fungicide evaluated by DowElanco.
APPLICATIONS:
ModeofactionCan be applied as a foliar spray and penetrates into plant tissue very
rapidly where it is transported acropetally. Shows curative, eradicant and protectant
activity. Uses Control of powdery mildew on wheat and barley. Can be mixed with azole
fungicides to give broad-spectrum control of cereal diseases. Formulation types EC.
Oral Acute oral LD50 for rats >5000, mice >500 mg/kg. Skin and eye Acute percutaneous
LD50 for rabbits >2000 mg/kg. Slight skin and eye irritation (rabbits). Other No evidence
of teratogenicity and negative in the Ames test.
ECOTOXICOLOGY:
Birds Acute oral LD50 for adult bobwhite quail >2000 mg/kg. Dietary LC50 (8 d) >5000
ppm in diet. Fish LC50 (96 h) for bluegill sunfish >100, rainbow trout 50100 mg/l.
Daphnia LD50 (24 h) >100 mg/l.
xylachlor
Herbicide
NOMENCLATURE:
Common name xylachlor (WSSA)
IUPACname 2-chloro-N-isopropylacet-2,3-xylidide
Chemical Abstracts name 2-chloro-N-(2,3-dimethylphenyl)-N-(1-methylethyl)acetamide
CASRN[63114772] DevelopmentcodesAC206 784
SmilescodeCC(C)N(C(=O)CCl)c1cccc(C)c1C
PHYSICAL CHEMISTRY:
Mol. wt. 239.7 M.f. C13H18ClNO
COMMERCIALISATION:
History Herbicide evaluated by American Cyanamid Co.
PRODUCTS:
Discontinued products Combat* (Cyanamid).
554 xylachlor
xylylcarb
Insecticide
OCONHCH3
CH3
CH3
IRAC1A; carbamate
NOMENCLATURE:
Common name xylylcarb (BSI, E-ISO, (m) F-ISO); MPMC (JMAF)
IUPACname 3,4-xylyl methylcarbamate
Chemical Abstracts name 3,4-dimethylphenyl methylcarbamate CASRN[2425107]
ECno2193649 DevelopmentcodesS-1046; S-21046 (both Sumitomo Chemical)
SmilescodeCNC(=O)Oc1ccc(C)c(C)c1
PHYSICAL CHEMISTRY:
Mol. wt. 179.2 M.f. C10H13NO2 Form Colourless solid. M.p.7980C; (tech.,
71.576C) V.p. 121 mPa (25C) Solubility In water 580 mg/l (20C). In acetonitrile
930, cyclohexanone 770, xylene 134 (all in g/kg). Stability Hydrolysed in alkaline media.
COMMERCIALISATION:
History Insecticide reported by R. L. Metcalf etal. (J. Econ. Entomol., 1963, 56, 862).
Introduced by Sumitomo Chemical Co., Ltd.
Manufacturers Sumitomo Chemical
APPLICATIONS:
Uses Control of hoppers and other sucking insects on rice; and leafhoppers, planthoppers,
and scale insects on fruit. Formulation types DP; EC; MG; WP.
PRODUCTS:
Discontinued products Meobal* (Sumitomo Chemical).
ANALYSIS:
Product analysis by hplc (S. Sakaue et al., Nippon Nogei Kagaku Kaishi, 1981, 55, 1237) or by
uv spectrometry. Residues determined by glc of a derivative with ECD (J. Miyamoto et al.,
Nihon Hoyaku Gakkaishi, 1978, 3, 119).
percutaneous LD50 for rats >1000 mg/kg. Toxicity Class WHO (a.i.) II
xylylcarb 555
ENVIRONMENTAL FATE:
Insecticides).
zarilamid
Fungicide
NOMENCLATURE:
Common name zarilamide ((m) F-ISO); zarilamid (BSI, E-ISO, not Brazil)
IUPACname (RS)-4-chloro-N-[cyano(ethoxy)methyl]benzamide
Chemical Abstracts name ()-4-chloro-N-(cyanoethoxymethyl)benzamide
CASRN[84527515] unstated stereochemistry
DevelopmentcodesICIA0001; PP001 SmilescodeClc1ccc(cc1)C(=O)NCOCCC#N
PHYSICAL CHEMISTRY:
Mol. wt. 238.7 M.f. C11H11ClN2O2 Form Pale brown crystals. M.p.111C
V.p. 0.0047 mPa (20C) Henry 6.72 106 Pa m3 mol1 (calc.) S.g./density 1.34 (25C)
Solubility In water 167 mg/l (pH 5.3, 20C). In acetone >500, dichloromethane, methanol
271, ethyl acetate 336, hexane 0.12, toluene 26 (all in g/l, 20C). Stability Stable >0.75 y
at ambient temperature; DT50 (hydrolysis) 18 d (pH 5), 6 d (pH 7).
COMMERCIALISATION:
History Fungicide reported by S. P. Heaney etal. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis.,
2, 551). Evaluated by ICI Agrochemicals.
APPLICATIONS:
ModeofactionAnti-microtubular fungicide.
percutaneous LD50 for rats >2000 mg/kg. Mild irritant to eyes.
ECOTOXICOLOGY:
Daphnia LC50 5.65 mg/l. Bees LD50 (contact) for honeybees >0.2 mg/bee.
zolaprofos
Insecticide
IRAC1B
NOMENCLATURE:
Common name zolaprofos (BSI, E-ISO, (m) F-ISO)
IUPACname O-ethyl S-3-methyl-1,2-oxazol-5-ylmethyl S-propyl phosphorodithioate;
O-ethyl S-(3-methylisoxazol-5-ylmethyl) S-propyl phosphorodithioate
556 zolaprofos
Chemical Abstracts name O-ethyl S-[(3-methyl-5-isoxazolyl)methyl] S-propyl

phosphorodithioate CASRN[63771697] DevelopmentcodesBAS 268I;
BAS 26800-I (both BASF) SmilescodeCCCSP(=O)(OCC)SCc1cc(C)no1
PHYSICAL CHEMISTRY:
COMMERCIALISATION:
History Insecticide evaluated by BASF AG.
APPLICATIONS:
zolaprofos 557

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A World Compendium

The Pesticide Manual

Supplementary Entries Extended

Promoting the science and practice of sustainable crop production

ISBN 978 1 901396 86 7

First published 1968 Seventh edition 1983 Thirteenth edition 2003

ACD 10614; ACD 10435

iodine or electrophotometric determination (J. Haslam & G. Newlands Analyst, 1955,

Details PM12, Entry 15.

ECno2062158 DevelopmentcodesCompound 118 (Hyman)

Product analysis by measurement of the bromine added across the double-bond or

TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:

Chemical Abstracts name 3-(dimethylamino)-6-(1,1-dimethylethyl)-4-methyl-1,2,4-

History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch.

amiton; amiton hydrogen oxalate

Chemical Abstracts name ()-(1-aminopropyl)phosphonic acid

decline is found after intravenous administration in rats. Whole body autoradiograms of

Other names TDDA; TTCA CASRN[3586605]

Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylethyl)-1,3,5-triazine-2,4-

HRACE WSSA 14; triazolinone

No. 2). Was mainly used in glasshouses as a smoke.

120 d produces no histopathological changes, apart from cholinesterase inhibition at

PHYSICAL CHEMISTRY: Mol. wt. 1344.7 M.f. C84H111FeN12

V.p. Non-volatile Solubility In water 5 mg/l (room temperature). Dissolves readily in

Chemical Abstracts name 4-dodecylbenzenesulfonic acid compound with

carp 1.0, trout 2.0 mg/l. Bees Not toxic to bees.

FRAC14, F3; aromatic hydrocarbon

blasticidin-S; benzylaminobenzenesulfonate (BABS) salt

blasticidin-S; benzylaminobenzenesulfonate (BABS) salt 53

TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:

Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl) O,O-

Toxicity Class WHO (a.i.) II ECClassification T; R24/25| N; R50, R53

Chemical Abstracts name (Z)-2-chloro-N-[(2-butenyloxy)methyl]-N-(2,6-

Chemical Abstracts name 3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-

3-pyridinylcarbonimidodithioate CASRN[51308544] DevelopmentcodesS-1358

PHYSICAL CHEMISTRY: Mol. wt. 327.5 M.f. C8H14Cl3O5P

[13250129] (R)-sec-butylamine; [513495] (S)-sec-butylamine ECno2377327 (RS)-

cadmium calcium copper zinc chromate sulfate

calcium and lead arsenate

calcium and lead arsenate 79

TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:

Chemical Abstracts name 2-chloro-4,5-dimethylphenyl methylcarbamate

IUPACname carbon disulfide

IUPACname carbon tetrachloride; tetrachloromethane

HRACO WSSA 4; benzoic acid (auxin)

Toxicity Class WHO (a.i.) U

chlordimeform; chlordimeform hydrochloride

ornamentals, tomatoes, tobacco, cucurbits, brassicas, lettuce, beans, capsicums, aubergines,

PHYSICAL CHEMISTRY: Mol. wt. 242.7 M.f. C11H15ClN2O2

chlorfluren; chlorfluren-methyl 111

Chemical Abstracts name 2-chloro-9H-fluorene-9-carboxylic acid CASRN[24539

APPLICATIONS: Uses Controls Ixodidae including strains resistant to other ixodicides.

Chemical Abstracts name 3-(4-chlorophenyl)-5-methyl-2-thioxo-4-thiazolidinone

4-chlorophenyl phenyl sulfone

2-chlorovinyl diethyl phosphate

HRACC2 WSSA 7; urea

chlorphonium chloride 121

Bayer 78182 SmilescodeCCOP(=S)(OCC)ON=C(C#N)c1ccccc1Cl

HRACL WSSA 20; benzonitrile

clofencet-potassium; clofencet 133

134 clofop; clofop-isobutyl

copper zinc chromate

Chemical Abstracts name 3-[1-(2-furanyl)-3-oxobutyl]-4-hydroxy-2H-1-