Agricultural and Biological Chemistry

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Stink Bug Aldehydes

Takahiko Tsuyuki, Yukiji Ogata, Izuru Yamamoto & Kengo Shimi

To cite this article: Takahiko Tsuyuki, Yukiji Ogata, Izuru Yamamoto & Kengo Shimi
(1965) Stink Bug Aldehydes, Agricultural and Biological Chemistry, 29:5, 419-427, DOI:
10.1080/00021369.1965.10858405

To link to this article: https://doi.org/10.1080/00021369.1965.10858405

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[Agr. BioI. Chern., Vol. 29, No.5, p. 419-427, 19651

Stink Bug Aldehydes

By Takahiko TSUYUKI,t Yukiji OGATA,**
Izuru YAMAMOTO** and Kengo SHIM I
College of General Education, The University of Tokyo
**Department of Agricultural Chemistry, Faculty of Agriculture
Tokyo University of Agriculture
Received November 21, 1964

The odorus and physiologically active substances of the secretions of Japanese stink bugs
(six kinds of Pentatomidae and three kinds of Coreidae bugs) were identified. The secre-
tions of Pentatomidae bugs contained trans 2-decenal as a main component. In the secre-
tions of Coreidae bugs n-hexanal was always found and in the case of Acanthocoris
sordidus trans 2-hexenal was a main component.

INTRODUCTION could be collected at one time and at one

In recent years the nature of pheromones
and other chemical releasers used by insects
has aroused considerable interest. A few
investigations have been published on the
chemical structures or physiological functions
of these substances.
It is well known that most stink bugs eject
detestable secretions, which have some phy-
siological activities. Among them is remark-
able killing or repelling activity against ants. l )
We also noticed that the secretion from one
stink bug could kill thirty ants in a vessel
within thirty minutes.
We have investigated the odorus and physio-
logically active substances of the Japanese
stink bugs and identified the aldehyde com-
ponents of the secretions of six kinds of
Pentatomidae bugs and three kinds of Coreidae
bugs and compared them with Blum's21 and
Waterhouse's!) results.
RESULTS
Because of small number of bugs which
t Present Address: Department of Chemistry. Faculty of
Science. University of Tokyo.
1) D. F. Waterhouse. D. A. Forss and R. H. Hackmann. J.
Ins. Physioi. 6. 113 (1961).
2) M. S. Blum. J. G. Traynham. and J. B. Chidester and
1. D. Boygus. Science. 132. 1480 (1960).
place, the method of isolation, purification
and identification were limited. The typical
procedure of extraction is shown in Fig. 1.
\Nhen extracts, which were obtained with
petroleum ether from bugs, were treated with
Brady's reagent (2,4-dinitrophenylhydrazine),
detestable odors disappeared. This indicates
that the major odor us components are carbonyl
compounds.
However, there remained a slight aromatic
odor in the case of Hygia opaca, indicating that
non-carbonyl compound-possibly ester-contri-
butes to a part of the odor of this species.
A mixture of 2,4-dinitrophenylhydrazones
(2,4-DNPs) were satisfactorily separated by
reversed phase paper or thin layer chromato-
graphy. In both Pentatomidae and Coreidae
bugs, n-alkanal and trans 2-alkenal were identi-
fied in the form of 2,4-DNPs. Usually the
natural sample showed several spots on the
chromatogram and carbon atom numbers of
an aldehyde can be estimated from the Rp
value. Each spot was extracted from the
paper and Amax * in methanol measured.
n-Alkanal 2,4-DNPs showed Amax at 360 m.u
and trans 2-alkenal 2,4-DNPs at 372 to 378 mp..
* Ultra violet spectra were measured for methanol solution.
420 Takahiko TSUYUKI, Yukiji OGATA, Izuru YAMAMOTO and Kengo SHIOMI

bugs, irritated

extraction with petro ether

at room temperature.
I
,---------~---------

insect bodies petr. either layer (odor of stink bug)

Brady's reagent
(ZA-dinitrophenylhydrazine)
I
petro ethereal layer with red ppt.
(disappearance of the odor)
I filtration
I I
m. p. 265°C filtrate
I was h'109
I Wit. h water
concentration

mixture of DNPs

separation by reversed phase paper chromatography

ba~d2 band.
purification by column chromatography
a DNP
m.p.
mixed m. p.
paper strip chromatography
U.V.
I. R.
FIG. 1. Procedure for Separating Odorous Principles from Stink bug.

TABLE I. STINK BUG ALDEHYDES 2,4-DNPs

m.p.
Insect DNP of (0C) A ~:~H (mp) 1. R.

Nazara viridula 131- 15 mg trans 2-decenal 127 378 *

Graphosoma rubrolineatum 52-5.4 mg trans 2-decenal 127 376 *
trace n-hexanal? 363
Menida Scotti 446- 40 mg trans 2-decenal 127 378 *
321- 20 mg trans 2-decenal 127 378 *
Aelia fieberi 270-0.5 mg trans 2-decenal 127 376
trace trans 2-octenal? 375
Nezara antennata 29- 2 mg trans 2-decenal 125~6 376 *
Scotinopha lurid,a 291- 1 mg trans 2-decenal 126.5 378 *
trace trans 2-octenal? 375
Acanthocoris sordidus 615- 30 mg trans 2-hexenal 147.5~6 377 *
10 mg n-hexanal 102 365 *
Hygia opaca 68- 73 mg n-hexanal 103~4 360
Plinachtus bicoloripes 20- 3 mg n-hexanal 100 359
trace n-octanal? 358
 Stink Bug Aldehydes 421

TABLE II.
Insect Common name Aldehyde identified
Pentatomidae
Ne;;ara viridula (L.) Minamiao-kamemushi trans 2-decenal *
Nezara viridula var. Green vegetable bug 2-decenal
smaragdula (F.) 2-hexenal
Graphosoma rubrolineatum Akasuji-kamemushi trans 2-decenal *
(Westw.) n-hexanal ?*
Menida Scotti (Puton) Scott-kamemushi trans 2-decenal
Aelia fieberi Scott Uzura-kamemushi trans 2-decenal *
Nezara antennata Scott Aokusa-kamemushi trans 2-decenal*
Scotinophara lurida Kuro-kamemushi trans 2-decenal*
Burmeister
Rhoecocoris sulciventris1 ) Bronze orange bug 2-octenal
(Stahl) 2-hexenal
Poecilometis strigatus1 ) 2-hexenal?
Westw. 2-octenal?
Brochymena quadripustulata 3 ) (F.) trans 2-hexenal
Oebalis pugnax (F.) Rice stink bug trans 2-heptenal
Dolycoris baccarum L. 4) 2-hexenal
2-octenal
2-decenal
Eurogaster spec. 4 ) 2-hexenal
2-octenal
Palomena viridissima P.4) 2-hexenal
2-octenal
2-decenal
Coreidae
Acanthocoris sordidus Hozuki-kamemushi n-hexanal*
(Thunberg) trans 2-hexenal *
Hygia opaca (Uhler) Tsumaki-herikamemushi n-hexanal*
Plinachtus bicoloripes Kibara-herikamemushi n-hexanal*
Scott n-octanal ?*
Mictis profama F. Crusader bug n-hexanal
Amorbus rubiginosus Guer. Eucalyptus bug n-hexanal
Cimex
Cimex lactularius P.4) Bettwanze 2-hexenal
2-octenal
Eurycotis jloridana W. 3 ) hexenal
Cremastogaster africana Mayr.5) hexenal
* Our work.

Usually the structures were confirmed by
conventional methods as described in experi-
mental section. When amount of 2,4-DNPs
3)LM. Roth, W. D. Niegisch and W. H. Stahl, Science,
123, 670 (1956).
4) H. Schildknecht, K. Holoubek, K. H. Weis, H. Vetter
and H. Kramer Angew. Chem., 75, 762 (1963).
5) C. W. Bevan, A. J. Birch and H. Caswell, J. Chem. Soc.,
1961,488.
obtained was not enough for this identifica-
tion, the structures were inferred from the
RF and Amax values.
The results are shown in Table I. Main
components were always trans 2-decenal in
the case of Pentatomidae family, and both
male and female Scott bugs gave the same
422 Takahiko TSUYUKI, Yukiji OGATA, Izuru YAMAMOTO and Kengo SHIOMI
results. In the case of Coreidae family, n-
hexanal was always found and trans 2-hexenal
was also found in A. sordidus. Hexanal,
octenal and trans 2-octenal as minor compo-
nents were tabulated together, which were
inferred only from the RF and Amax values of
their 2,4-DNPs (indicated by question marks
in the table).
2,4-DNP, which melted at 265°C, was often
found in the both families. It consisted of
red crystals and gave Amax at 411 mu in
chroloform. Although the melting point and
-Amax value were similar to those of p-toluqui-
none bis 2,4-DNP(m.p. 269°C), they were not
identical in Amax and RF values. Waterhouse
-described 2,4-DNP of m.p. 268°C and Amax
410 mp. showing absorption at 1692 cm- 1
However our sample of m.p. 26SOC showed
no absorption at 1692 cm- 1 •
Synthetic trans 2-alkenals have detestable
-odors like bug secretion and show killing and
repelling action to ants. For example, when
~ piece of filter paper spotted with a few mg
-of synthetic trans 2-decenal was placed in a
.Petri-dish, all thirty ants(Lasius Niger Linne)
RCH2CH2CHO+Ac20(KOAc)
RCHzCHBrCH(OMejz
t
KOH (in BuOH) H+
RCH=CHCH (OMe)z
1
NO z
H 2NNH-<_I- N02
RCH=CHCH=NNH-<_I-N02
were killed within one hour, whereas the
control lived more than a week. Details will
be reported in another communication.
The stink bug aldehydes, which have been
discovered by several workers, are summariz-
ed in Table II, together with trans 2-hexenal
6) Paul z. Bedoukian, J. Am. Chern. Soc.,
from a cookroach, E. jloridana and an ant,
C. africana.
n-Alkanal and trans 2-alkenal are widely
spread through-out Pentatomidae, Coreidae
and Cimex families, and these aldehyde com.
ponents in the secretions of stink bugs caused
the death of ants. Therefore, it is suggested
that the aldehyde is the chemical releaser
which the bug uses for defence.
EXPERIMENTAL
1. Authentic samples.
n-Alkanal 2,4·DNPs. Commercially available n-
alkanals were distilled, and their 2,4-DNPs were pre-
pared by the usual method with Brady's reagent.
trans 2-Alkenals and their 2,4-DNPs. trans 2-
Alkenals were synthesized from the corresponding n-
alkanals according to the Bedoukian's method. 61 In-
termediately obtained acetals were converted to 2,4-
DNPs by treating with Brady's reagent.
The synthetic 2-alkenals and 2,4-DNPs were proved
to be in trans form by absorption at 980 cm- 1 in
infrared spectra.
2. Chromatography.
Paper chromatography. The filter paper (Taya
Roshi No. 51) was pretreated with benzene solution
---;>- RCH 2CH=CHOCOCH a
MeOH
Brz (in CCI.)
RCHzCHBrCHBrOCOCH a
t
-----> RCH=CHCHO
,,=
NO z
" R=CH a (CH z)-, n=3,4,5,6,7,9
containing 3% liquid paraffin and dried at room tem-
perature. Samples were spotted on the paper and
developed with the mixture of methanol-chroloform-
water (10: 10: 1 vjv).
Typical reversed phase paper chromatogram of the
authentic 2,4-DNPs of n-alkanals and trans 2-alkenals
is shown in Fig. 3.
79, 889 (1957). From the comparison of RF values of various 2,4-
 Stink Bug Aldehydes 423

Wavelength (p)

l002r·5~__~3r·O~__~4T·O~~5r·()~________~6r·O~____~7~.O____J8~.O~~9~.0~~1~0~lfl-11~2Jl~3jl~411~5~16~

n- Hexanal 2,4- DNP

4~~0~0---C3~,2~OOC---02,~4NOO'---'1,~90~O~--~1,~70~O~--,t~--~~--~~~--~~--~7~070~
Wavenumber (em-i)
Wavelength (p)
l002f·~5__~3~.O~____~47·0~~5~.O~________~6.~II______~7{.O~__~8.~O____9~.~O__~lO~~lAl~1~~?~1~3~1~4~1~5~1~6

"o 80
.;;;
<II

.~ 60
c: 2-Hexenal 2,4-dinitrnphcnyl-
~ hydrazone
40

20

4~~OmO----3,,2~O~O~--02,~40~O~--'1~,9~Or~J--~1~,7~O'O~~~'----*~~--71,~lO~O~---9~O~O-----=70~O~~
Wavenumber (em- 1 )
Wavelength (II)

lo0f2.~5__~3~.O~__~4T·O~~5T·O~~~==~6T·O~____~~__~__~~~~~~~~~

80
c:
.~
.§ 60
Ul 2- Decenal 2.4-dinitrophenyl-

..
.P"" 40
hydrazone

"~" 20
p';

4~~omO----3o,~20VO~--02,~4NOO~--~1,,9~O~O----1~,7~O~O----~1,+50~O~--~1~,3~OO~--~1~,I~OO~--~9(L)O~--~7~OO~~
Wavenumber (em-i)
FIG. 2.

DNPs, it was concluded that following relationships
exist between RF values and structures of 2,4-DNPs.
1) 2,4-DNP with longer carbon chain shows lower
RF value.
2) When n-alkanal and trans 2-alkenal of the same
number of carbon atoms are compared, the RF
value of the latter is alwayer higher than that
of the former.
Generally the following relation was found,
Cn£1>Cn> C(n+ 1)£1> Cn+ 1
where Cn and Cn£1 refer to the RF values of 2,4-DNPs;
 424 Takahiko TSUYUKI, Yukiji OGATA, Izuru YAMAMOTO and Kengo SHIOMI

1.0

0.9

0.8

0.7

0.6

0.5
~
0.4

0.3

0.2

0.1

10 12
32> 42> 72> 92> 1M 122>
Carbon number of aldehyde
FIG. 3. Reversed Phase Paper Chromatogram.
Toyo·roshi No. 51, pretreated with liquid paraffin. Development with CH.OH-CHCI •.
H20 (10: 10: 1) for 14 hours at room temperature.

<of carbon number "n", n-alkanal and trans 2-alkenal DNP.

-respectively.
Thin layer chromatography. The following pre-
paration of thin layer plate was critical for successful
-separation of 2,4-DNPs.
The glass plate was coated with the mixture of
"Silica gel(Silica gel G for thin layer chromatography,
Merck), anhydrous gypsum and water (25: 5 : 60 w/w),
with thickness of 0.25 mm, dried at room temperature.
The plate was treated with benzene solution contain-
ing 3% liquid paraffin, then heated for one hour at
100°C.
The solvent system for developing was methanol-
-chroloform-water (3: 3 : 1 v/v). The relations of RF
values were same as those of the paper chromato-
-graphy. Thus, the estimation of carbon numbers of
aldehyde was possible by either method.
Column chromatography. By column chromato-
-graphy, the isolation of minor components was im-
possible. The gas chromatographic separation of free
.n-alkanal has been reported.
Gas chromatography. Attempted separation by
flash exchange method7 ) using 2,4-DNP and 2-ketoglu-
iaric acid or the other keto acids was unsuccessful,
because the pyrolysis condition varied with each 2,4-
3. NMR spectra
The NMR spectrum of a 2,4-DNP gave much in-
formations about its structure.
Aldehyde was distinguished from ketone by the
presence of peak at 0 7.5-7.7, the estimation of the
number of carbon atoms and the detection ofunsatu-
ration and branched chain structure were also possible.
Therefore, this method was the most recommendable
for identification.
The NMR spectrum of trans 2-decenal 2,4-DNP
from Menida Scotti and n-hexanal 2,4-DNP from
Hyginia opaca are shown in Fig. 4. They were identical
with those of the authentic samples.
4. Pentatomidae family
Nezara viridula (L.). Southern green stink bug,
Minamiao-kamemushi.
The secretion from 131 examples of male and female
adults, which were reared from nymphs, collected in
the paddy field in Kochi Prefecture, was extracted
with petroleum ether and treated as shown in Fig. 1.
The red crystal, which showed m.p. 265°~ after re-
crystallization, was filtered off, and the filtrate was
7) Jack W. Rall, Anal. Chem. 32, 332 (1960).
 Stink Bug Aldehydes
concentrated. The residue was purified by silica gel
column chromatography, followed by recrystallization
from petroleum ether. The yellowish orange crystal
weighed 15 mg and gave m.p. 127°C and Amax 378
mil (e 28,8000). Anal. Found: C, 58.02; H, 6.92;
N, 16.62%, Calcd. for C 16 H zzO,N,: C, 57.47; H,
6.63; N, 16.76%. A mixture with the same deriva-
tive of synthetic trans 2-decenal of m.p. 126.5-
127.0°C, showed no melting point depression, and
the infrared spectrum of the sample was identical
with that of the authentic trans 2-decenal 2,4-DNP.
Graphosoma rubrolineatum (Westw.), Akasuji-
kamemushi.
The 2,4-DNP mixture, obtained from 52 examples of
male and female adults which infested on the flowers
of fennels in Chiba Prefecture according to the above
mentioned procedure was separated by the reversed
phase paper chromatography. From the band of RF
0.36 was obtained 5.4 mg of yellowish orange crystal,
which showed m.p. 127°C and J.max 376 mp., and
the infrared spectrum was identical with the authentic
trans 2-decenal 2,4-DNP. A mixture with the authen-
tic sample showed no melting point depression.
The yellowish orange crystal obtained from the
band of RF 0.58 was inferred to be n-hexanal 2,4-
DNP from Amax value (363 mp.) and RF value.
Menida Scotti (Puton), Scott-kamemushi.
Three hundred and twenty-one examples of male
,and 446 examples of female adults which were over-
wintering indoors at Yudanaka in Nagano Prefecture
were treated by the same procedure as in N. viridula
.and 20 mg (from male) and 40 mg (from female) of
.trans 2-decenal 2,4-DNP were obtained, m.p. 126.5-
127 .O°C (both samples), Amax 378 mp. (e 28,800) (both).
Anal. Found: C, 57.27; H, 6.74; N, 16.06% (male
;sample). C, 57.33; H, 6.76; N, 16.72 (female sample),
·Calcd. for C 16 H zzO.N,: C, 57.47; H, 6.63; N, 16.76%.
A melting point in admixture of each sample with
the authentic sample produced no melting point de-
·pression.
Aelia fieberi Scott, Uzura-kamemushi.
Two hundred and seventy example of male and
female adults which infested on grasses in Osaka City
were treated as shown in Fig. I. The reversed phase
paper chromatogram of 2,4-DNP mixture gave two
bands.
From the band of RF 0.51, 0.5 mg of yellowish
·{)range ~crystal, melting at 127°C and showing Amax
376 mp., was obtained on purification by column
.chromatography. The RF value on the paper or the
425
thin layer chromatogram was identical with that of the
authentic trans 2-decenal 2,4-DNP and a mixture with
the authentic sample showed no depression in melting
point. From the second band of RF 0.60, not much
crystal was obtained to allow melting point measure-
ment.
However, Amax value (375 mp.) and RF values of
paper and thin layer chromatogram of the sample was
identical with those of trans 2-octenal 2,4-DNP.
Nezara antennata Scott, Aokusa-kamemushi.
From 29 examples of male and female adults, which
infested on the leeks in Machida City, Tokyo, about
2 mg of trans 2-decenal 2,4-DNP was obtained by
silica gel column chromatography and recrystalliza-
tion. It melted at 127°C and gave Amax at 376 mp..
The infrared spectrum was identical with the authen-
tic sample.
Scottinophara lurida Burmeister, Kuro-kame-
mushi.
Two hundred and ninety-one examples of male and
female adults which were over-wintering in the ground
in Fukui Prefecture were treated as shown in Fig. I.
By silica gel column chromatography, about I mg
of yellowish orange crystal melting at 127°C was
obtained. By comparison of infrared spectrum, ultra-
violet spectrum (Amax 378 mp.) and mixed melting
point with that of the authentic sample, it was
identified as trans 2-decenal 2,4-DNP. From both RF
value on paper chromatogram and Amax value (375
mp.), the presence of trans 2-octenal was inferred, but
the melting point could not be measured.
5. Coreidae family .
Acanthocoris sordidus (Thunberg), Hozuki-
kamemushi.
2,4-DNP mixture, obtained from 615 examples male
and female adults, which were infested on the straw-
berry tomatoes in Gumma Prefecture was separated into
two kinds of the hydrazones. The first eluted hydra-
zone was recrystallized from petroleum ether and gave
a constant melting point of 102°C. The RF value on
the paper chromatogram was identical with that of
the authentic n-hexanal 2,4-DNP (m.p. 103°G), but
Amax was 365 mp, whereas the authentic n-alkanal
2,4-DNPs showed absorption maxima at 360 mp..
Anal. Found: C, 51. 77; H, 5.65; N, 19.86%, Calc.
for C1zH1SO.N,: C, 51.42; H, 5.75; N,.19.99%. In
infrared spectrum, absorption at 980 cm- 1 indicated
the presence of trans double bond. The NMR spect-
rum of this hydrazone is shown in Fig. 3. By com-
parison of the peak areas of CHa and CH=CH, it was
426 Takahiko TSUYUKI, Yukiji OGATA, Izuru YAMAMOTO and Kengo SHlOMJ

n-hexana I 2,4- dinitrophenyl-hydrazone

! !
9.0 8.0 7.0 6.0 5.0 3.0 2.0 1.'0 op.p.m.(b')

2-decenal 2, 4-dini trophenyl-hydrazone

CH,ICH,),CH=CH-CH=N NH-V-NO,

NO,

'--;lcfl7i.o----;1-r(o.7io-----,9~.0n----"'l8~.0)-?7"r.0.-------;;6.'nO----i57\0---;4;-';.0)----;;3:1r.O.------,,2.J,;0---1;-\.0,,----I;O~pp.m. 18'

2,4-DNP from Acanthocoris sordidus (Thunberg)

H.O 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 op.p.m.(I
FIG. 4.
 Stink Bug Aldehydes
concluded that the hydrazone was a mixture of n-
hexanal 2,4-DNP and trans 2-hexenal 2,4-DNP in the
ratio of 2; 1. In fact, the mixture in 'this ratio gave
Amax at 365 mf.!.
The fraction which was eluted later gave about
30 mg of orange crystal on crystallization melting
at 146.5-147.0°C, and Amax 377 mf.! (0 29,300).
Anal. Found: C, 51. 55; H, 5.12; N, 19.57% Calcd.
for C12H I40.N4: C, 51.79; H, 5.07; N, 20.14%. The
infrared spectrum was identical with that of the
authentic trans 2-hexena1 2,4-DNP and mixed melting
point gave no depression.
Hygia opaca (Uhler), Tsumaki-herikamemushi.
Sixty eight examples of male and female adults,
which infested on the sterns of the sun flowers in
Yokohama City, Kanagawa Prefecture, were used.
By recrystallization of the hydrazone mixture, 73 mg
of yellowish crystal of m:p. 103-104°C and Amax
360 mf.! was obtained.
The infrared spectrum and RF value were identical
with those of the authentic n-hexana1 2,4-DNP and
the mixed melting point showed no depression. In
the filtrate above obtained there remained a slight
ester-like odor, but the structure was not determined.
A paper chromatogram of the filtrate showed the
presence of a trans 2-alkenal 2,4-DNP (Amax 372 mf.!)
which was higher than 2-decenal.
Plinachtus bicoloripes Scott, Kibara-herikame-
mushi.
427
Twenty examples of male and female adults, which
infested on the spindle tree in Nerima, Tokyo, were
used. By the 'paper chromatographic separation of a
hydrazone mixture, two bands were obtained. From
the band of a higher RF value (RF 0.49) gave 0.3
mg of "l yellow crystal, which melted at 100°C and
showed Amax 359 mf.! and the infrared spectrum was
identical with that of the n-hexanal 2,4-DNP; a mixed
melting point showed no depression. From the band
of a lower RF value (RF 0.43), presence of a n-
octanal 2,4-DNP was inferred by comparing RF value
and Amax value (358 mf.!) with those of the authentic
sample;
Acknowledgement. The authors are grateful
to Prof. Minoru Ohno, Kyoto University for
kindly supplying the authentic trans 2-hexenal
2,4-DNP, and Prof. Ryo Yamamoto, Tokyo
University of Agriculture for his encourage-
ment and to Miss Setsuko Kitamura* for her
assistance in the experimental work through-
out the study. Also the the authors are in-
debted to Mr. Shuji Tachikawa, Tokyo
University of Agriculture for the identifi-
cation of insects. This work was supported
in a part by a grant-in-aid from Ministry of
Education.
* Akenohoshi Gakuen, 5·2 Namiuchi, Aomori City, Aomori
Prefecture.