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benalaxyl O
O
N
metalaxyl
N
NH
N
O
N
H
fuberidazole N O N N oximino- O
Cl N H O Cl F N
O O O S
N
H
N
H
O
S N O O O F
F O Cl
O O O
N N
O acetates O
H
O N N O O H N O
S F Cl S
HO H H N O N
O O N O N furametpyr Cl F O sedaxane N O N
N
Si
O N N thiophanate NH O H N H N
N
H bixafen O O
N O
O N S O O Sn
N N benomyl N N N N O
famoxadone
H thiabendazole F N H OH
N N N O azoxystrobin orysastrobin silthiofam
NH H H diethofencarb N
N O pyraclostrobin fentin hydroxide
H thiophanate- O imidazolinones
ofurace oxadixyl ethirimol O thiophanates methyl penflufen penthiopyrad isopyrazam
benzimidazoles Pyridinyl - ethyl - O O
N
carbendazim * negative cross-resistance to B1 phenyl-oxo-ethyl benzamides mandestrobin
butyrolactones oxazolidinones thiophene amide O
O
C5: uncouplers of oxidative phosphorylation
Thiazole - kresoxim-methyl NH
carboxamides N-methoxy-(penyl- O
H
N
O
S N O
# 29
F benzovindiflupyr N
F F Cl
ethyl)-pyrazole- N N O
N O
N dinitrophenyl crotonates
O 2,6-dinitro-aniline
A3: DNA / RNA synthesis (prop.) A4: DNA topoisomerase B3: B4: B5: B6: F O
F
F
carboxamides dimoxystrobin
O
F
N N pyrazine - picoxystrobin pyrametostrobin
F
# 32: heteroaromatics type II (gyrase) ß-tubulin assembly in mitosis cell division delocalisation actin/myosin/ F
F
F O
Br O
F
F
H
carboxamides I O
F F
O
fenamidone Cl
F
F F N O
# 31: carboxylic acids # 22 benzamides and (prop.) of spectrin-like fimbrin function N
N
H fluopyram O O
O HN
N
O
S Br N N
thiazole carboxamides H + + O O
# 20 phenylureas proteins e.g. in vesicle isofetamid
O flufenoxystrobin O
O
O
N N
O N
+
O
N H Cl
ethylamino-thiazole # 43 benzamides trafficking thifluzamide
pydiflumetofen benodanil Cl
O O O
N
N trifloxystrobin F F N
+
toluamide Oxathiin - O O
dihydro- O O
O O
carboxamide pyridinylmethyl-benzamide # 47 cyanoacrylates Pyridine - carboxamides
O
fluazinam
F
meptyl dinocap
metominostrobin dioxazines
H O carboxamides O N enoxastrobin
N
HO aminocyanoacrylates H O triclopyricarb benzyl-carbamates
O N
S O pyraziflumid O
O
O N
O
N
O O O
N O
S Cl O O H O O
Cl O Cl
Cl N N N +
N Cl N H H O O N
H
S N N N oxycarboxin N N O
oxolinic acid O S
Cl H H N Cl
N F N coumoxystrobin O O
hymexazole octhilinone (bactericide) N
H
Cl O N O
F F
mepronil N F O O
Cl
F H H F
O
O Cl
N +
F N
ethaboxam S N O HN O N O O
zoxamide pencycuron H O
binapacryl
isoxazoles isothiazolones fluopicolide Cl phenyl- O
boscalid carboxin furan - fenfuram fenaminstrobin fluoxastrobin
phenamacril benzamides pyraoxystrobin pyribencarb
carboxamides flutolanil
D: Amino Acid and Protein Synthesis E: Signal Transduction F: Lipid Synthesis or Transport / Membrane Integrity or Function I: Melanin Synthesis in Cell Wall
D1: methionine biosynthesis D2: D3: E1: signal transduction (mechanism unknown) E3: osmotic signal transduction F2: phospholipid biosynthesis F3: lipid peroxidation (prop.) F4: cell membrane F6: microbial disrupters of I1: reductase in I2: dehydratase in I3: polyketide
#13 azanaphthalenes melanin biosynthesis melanin biosynthesis synthase in melanin
(cgs gene) (prop.) protein synthesis protein synthesis MAP / histidine kinase (os-1, Daf1) methyltransferase # 14 aromatic hydrocarbons & heteroaromatics permeability, pathogen cell membranes # 16.1 Melanin Biosynthesis # 16.2 Melanin Biosynthesis biosynthesis
# 9 Anilino-Pyrimidines # 23 enopyranuronic acid # 24 hexopyranosyl antibiotics # 2 dicarboximides # 6 phosphorothiolates & dithiolanes O O fatty acids (prop.) # 44 Microbial (Bacillus sp.) Inhibitors: Inhibitors: # 16.3 Melanin Biosynthesis
aryloxyquinoline quinazolinone aromatic N
+
Cl N
O O
Cl Cl prothiocarb propamocarb Cl
OH
O Cl O N
strains: O Cl
cyprodinil O Cl
iprodione
Cl
pyrazophos S O tecnazene quintozene H
QST 713 Cl
blasticidin-S kasugamycin P I
fthalide
quinoxyfen proquinazid O
N
O
(TCNB) (PCNB) FZB24 diclocymet
O
MBI600 pyrrolo-quinolione
Cl iodocarb
NH Cl Cl
O Cl D747 cyclopropane carboxamide tolprocarb
O iprobenfos S O
N N D4: protein synthesis D5: protein synthesis E2: osmotic signal transduction chlozolinate O
N
O S
P S
O
P
O
biphenyl
# 25 glucopyranosyl # 41 tetracycline antibiotics MAP / histidine- kinase (os-2, HOG1) O
Cl
O
O F7: cell membrane F8: ergosterol F9: lipid homeostasis N O Cl
antibiotics # 12 phenylpyrroles (PP- fungicides)
mepanipyrim O
N O
Cl Cl edifenphos tolclofos-
Cl
disruption (prop.) binding and transfer/storage N
vinclozolin Cl
HO
dithiolanes methyl chloroneb # 46 plant extract # 48 polyene # 49 OSBPI Cl O
Chiral
HO
HO
O
Cl Oxysterol binding protein pyroquilon
O
OH O OH O O carpropamid
NH
HO
O
OH Cl Cl Cl Cl Melaleuca homologue inhibition
O H H
NH
OH
NH2 N N alternifolia triazolobenzo-thiazole propionamide
O OH procymidone O
N N
N N NH2
OH
N N O S
(Tea Tree Extract)
HN N NH OH OH S
H N
Cl
HN NH2
OH
F O
O S
O Plant oils (mixtures) N
oxytetracycline eugenol, geraniol N O Cl
O
pyrimethanil streptomycin (bactericide) Cl
F O N
dimethachlone etridiazole thymol natamycin N N
O
(bactericide) iso- H
fenpiclonil fludioxonil (pimaricin) piperidinyl-
prothiolane thiazole - S Cl
1,2,4-thiadiazole oxathiapiprolin
isoxazoline
tricyclazole fenoxanil
G: Sterol Biosynthesis in Membranes H:Cell Wall Biosynthesis P: Host Plant Defence Induction M: Chemicals with Multi-Site Activity
#M6 sulphamides
H4: chitin synthase H5: cellulose synthase P01: salicylic pathway P03: P04: P05:
G1: C14-demethylase in sterol biosynthesis (erg11/cyp51) G2:14-reductase and 8 7-isomerase in sterol # 19 Polyoxins # 40 Carboxylic Acid Amides benzothiodiazole BTH thiadiazole carboxamide
polysaccharide plant extract
#M09 anthraquinones #M05 chloronitriles
# 3 DMI-fungicides (DeMethylation Inhibitors) biosynthesis (erg2, erg 24) (CAA fungicides) O S N
(SBI: Class I) # 5 Amines(“Morpholines”) (SBI: Class II) OH Reynoutria #M01/02 inorganics O
O
N
Cl S O HO
HO
OH
sachalinensis S Cl Cl
OH
S
O
OH
N S
triazoles O piperazines N N HO
O
OHO
O
OHO
O
O
OH
OH
N H H OH
OH n
(Giant Knotweed S
O O NH2 N Cl
Cl Cl O
Extract) O N
N Cl O OH
acibenzolar- N Cl Cl Cl
N O HO
Cl
HN
O laminarin #M08 triazines dithianon
N Cl HO S-methyl sulphur chlorothalonil
O etaconazole HO N N piperidines H2N N
H
OH
isotianil
.
O
Cl
N
N
N O
O
N
OH
dimethomorph Cu Cl
N
N N Cl
NH
HN
P02: P06: Cl N
H
N #M04 phthalimides #M06 sulphamides
N Cl
Cl
O OH benzothiazole Bacillus cereus group copper
Cl preparations N N
azaconazole N ipconazole
HO pyridines triforine
O
(CH2) 11 N O Polyoxin B O
O N
Cl N H3C fenpropidin Cl
flumorph Cl O
O
O
Bacillus Cl O
N O S O
OH
N
N N
O
N S mycoides Cl N
Cl
N
H
O
Cl N N
anilazine S S
N Cl Cl O N
HO H
#M03 dithiocarbamates & relatives N S O
O Cl
pyridines aldimorph N
peptidyl pyrimidine nucleoside cinnamic acid O N
(Isolate J)
Cl Cl
F
N fenbuconazole N
tebuconazole N O
Cl
N N N O piperalin pyrimorph amides mandipropamid O Cl
N tiadinil
F probenazole captan
Cl Cl mandelic acid dichlofluanid
O Cl
F Cl Cl
(CH2) n N O
fenpropimorph
O
F
N amides N S 3+
bitertanol F metconazole F pyrifenox H3C Fe
N spiroketal- O O
Br
N
N
N
N
Cl
N
N
N
n = 10 to 13
n = 12: ~ 70%
amines
BM : Biologicals with Multiple Modes of Action S
ferbam
febram
3
N S
Cl Cl
Cl
F
S
N
S
O
N
#M10 quinoxalines
pyrimidines tridemorph Cl zinc thiazole
fluquinconazole tetraconazole pyrisoxazole O Cl
O Cl
N
N O
H
N O N
H
N BM01: BM02: O
Cl
Cl
O
O
O N
H
H
O O polypeptide lectin Trichoderma spp. metabolites
N O N O
N Cl N
F N Cl O captafol tolylfluanid
N O H S S
N OH morpholines dodemorph N S
H S
N S mancozeb H
bromuconazole myclobutanil N
N O iprovalicarb valifenalate Extract from the N S
Mn
2+
Si
N
F O N F Trichoderma N S
Zn (NH3)-
N S S N
H
F H cotyledons of H S 3 H S
S
O
spiroxamine O N
N
S atroviride x
N
N
N
H
O
lupine plantlets
Cl valinamide
Cl
N
N Cl N S chinomethionat
Cl (strain SC1) metiram S maneb Cl
flusilazole triadimefon nuarimol OH
benthiavalicarb
carbamates (BLAD) H
N S 2+
HO Cl Zn Cl
S N
H O Cl #M07 guanidines
N S
N Cl
HO N #M11 maleimides
N
N
S folpet
N F N
propineb
propineb
N
G3:3-keto reductase G4: squalene epoxidase in
cyproconazole F
HO
penconazole N
N
N O
imidazoles fenarimol
in C4-de-methylation sterol biosynthesis (erg1) Unknown Mode of Action NC : Not Classified N S
S
S
N N
S
S
2
Zn
2+
HN
NH2
N
H
NH
N
N
Cl Cl (erg27) # 18 (SBI class IV) HN
H
N
O N
Cl Cl thiram S
H
ziram NH2
O
flutriafol triadimenol # 17 (SBI :Class III) N S 2+ mixture of
O O N Zn
O Cl O O HO O S H iminoctadine iminoctadine
Cl O S
N
N O N
H - Cl
and other
Cl N hydroxyanilides O N N O O Cl
N N N H H P Al+++ N
H Mineral oils, organic oils, polyamines fluoroimide
Cl N Cl
N HO O Cl Cl potassium bicarbonate, zineb .
O Cl
difenoconazole OH
propiconazole imazalil allylamines N 3 Cl
H
N
N N material of biological
# 27 # 34 # U13 N
# U16
N
N N
HO N # 33 H3PO3 origin guazatine
Cl N N
O cymoxanil teclofthalam flutianil N
tebufloquin
N Si F F fosetyl-al
N
N O O Cl N
Cl Cl F H phthalamic cyano-methylene 4-quinolyl acetate
OH
hexaconazole HO F triticonazole triflumizole Cl
N
terbinafine
cyanoacetamide- ethyl- # 33
acid # U6 thiazolidine # U14 Legend:
N Cl
N oxime phosphonates phosphorous ferimzone
N O (antimycotic) cyflufenamid
N
triazolinthione fenhexamid acid mode of action group
C: Respiration
N O
N
Cl N
N
N pyrimidinone- Mode of action of fungicides based on the FRAC fungicide list
Cl O
phosphorous phenyl hydrazones (published at www.frac.info/publications )
diniconazole N S simeconazole Cl thiocarbamates sub-group
Cl Cl pefurazoate N amino-pyrazolinones naftifine acid acetamides
(antimycotic) O
Cl
The groupings can change when new results become known. C2: inhibition of complex II: target site of action
N HO N O +
N
N
S
Cl
N
N
N Cl H
N
S
O F
F
O
O Yellow zones represent accepted mode of action groups or in succinate-dehydrogenase (where known) or putative
Br O cases where resistance is known, cross resistance groups. In spite target site (=prop.)
F O
imibenconazole
Cl
HN
N
N
O
oxpoconazole
O N N O
N N
O
N
+
O F
O
O
# U17 OH
OH HO
of this general classification, cases of incomplete or even lacking # 7 SDHI (Succinate dehydrogenase
N Cl S
N S O O H
O O picarbutrazox HO O OH
cross resistance are known within some groups with some inhibitors)
N O Cl Cl Cl O H2N N FRAC code no. (#)
Cl prothioconazole N # 35 # 36 tetrazolyloxime HO
O
HO pathogens.
N N S # U08 N
H
OH
and group name
N triazoxide flusulfamide H
NH2
+ OH OH
N O
# 42 O metrafenone HO
pyributicarb N N Although details presented herein are accurate to our knowledge at chemical (sub-) group
epoxiconazole prochloraz benzene- H methasulfocarb # U18
fenpyrazamine (herbicide) benzotriazines # 37 Cl O the time of publication, neither FRAC nor its member companies
sulfonamides # U12 arylphenyl validamycin make any representation or warranty with regard to the content of
diclomezine # U08 thiazole carboxamides
•Temporary status; information on mode of action and thiocarbamates dodine ketones glucopyranosyl this presentation, in particular with regard to its correctness and
pyridazinones pyriofenone
/ or resistance risk is still uncertain guanidines antibiotic completeness. Neither FRAC nor its member companies assume
any liability for the content of this presentation or its use.
FRAC Mode of Action Poster ©
Updated March 2017