Journal of Chemical Ecology, 1Iol. 19, No. 4, 1993 C18 DIENES AS ATTRACTANTS FOR EIGHTEEN CLEARWING (SESIIDAE), TINEID (TINEIDAE), AND CHOREUTID (CHOREUTIDAE) MOTH SPECIES V. BIJDA 1'* U. MAEORG, 2 V. KARALIUS, 1 G.H.L. ROTHSCHILD, 3 S. KOLONISTOVA, 2 P. IVINSKIS, l and R. MOZORAITIS 1 ~ Institute of Ecology Akademijos 2, Vilnius, Lithuania 2Tartu University Jakobi 2, Tartu, Estonia 3Australian Centre for International Agricultural Research G.P.O. Box 1571, Canberra A.C.T. 2601, Australia (Received April 30, 1991; accepted December 3, 1992) Abstract-By screening singly and binary mixed 2,13- and 3,13-octadeca- dien-yl acetates and alcohols (2,13- and 3,13-18: Ac/OH)in Lithuania, Armenia, Azerhaijan, Turkmenistan, Ukraine, and the far east of Russia, sex attractants were discovered for 12 Sesiidae, four Tineidae, and one Choreu- tidae moth species. Males of Sesia yezoensis and Bembeciapuella as well as Nemapogonflavifrons were attracted by mixture of Z3,Z13-18:Ac/OH in a ratio of 9:1, Pyropteron sp. n. by the same mixture (ratio 1:9), Bembecia romanovi and B. zuwandica by Z3,Z13-18:AC and E3,Z13- 18:Ac (9:1), Synanthedon caucasicum by the same mixture in the opposite ratio (1:9), B. scopigera by 23,213-18:Ac and E2,Z13-18:OH in a ratio 9:1, Synasphecia triannuliformis by Z3,Z13-18:OH and E3,Z13-18:OH (9:1), Similipepsis takizawai and Archimeessia sp. n. by E3,Z13-18:OH and E2,Z13-18:Ac (1:1), Prochoreutis sechestediana by a mixture of E3,Z13-18:Ac plus E2,Z13-18:OH (1:), Microsphecia brosiformis by E3,Z13-18:Ac, Synanthedon conopiformis by the analogous alcohol, Synanthedon scoliaeformis and Nemaxera betulinella by E2,Z13-18:Ac, Triaxomera fulvimitrella by Z3,Z13-18:Ac. An analogous alcohol com- ponent is essential for the attraction of B. ichneumoniformis males. In- hibitors for B. romanovi, B. scopigera and B. zuwandica attraction were discovered. Preliminary data on attractants for six other species as well as on the diurnal rhythm of sexual activity of three species are presented. A new method for the stereoselective synthesis of 3,13-18:Ac/OH and E2,Z13-18:Ac/OH is described. *To whom correspondence should be addressed. 799 0098-0331/93/0400-0799507.00/0 1993Plenum Publishing Corporation
Transcript
Journal of Chemical Ecology, 1Iol. 19, No. 4, 1993
C18 DIENES AS ATTRACTANTS FOR EIGHTEEN CLEARWING (SESIIDAE), TINEID (TINEIDAE),
AND CHOREUTID (CHOREUTIDAE) MOTH SPECIES
V. B I J D A 1'* U. M A E O R G , 2 V. K A R A L I U S , 1 G . H . L . R O T H S C H I L D , 3
S. K O L O N I S T O V A , 2 P. I V I N S K I S , l and R. M O Z O R A I T I S 1
~ Institute of Ecology Akademijos 2, Vilnius, Lithuania
2Tartu University Jakobi 2, Tartu, Estonia
3Australian Centre for International Agricultural Research G.P.O. Box 1571, Canberra A.C.T. 2601, Australia
(Received April 30, 1991; accepted December 3, 1992)
Abs t rac t -By screening singly and binary mixed 2,13- and 3,13-octadeca- dien-yl acetates and alcohols (2,13- and 3,13-18: Ac/OH)in Lithuania, Armenia, Azerhaijan, Turkmenistan, Ukraine, and the far east of Russia, sex attractants were discovered for 12 Sesiidae, four Tineidae, and one Choreu- tidae moth species. Males of Sesia yezoensis and Bembeciapuella as well as Nemapogonflavifrons were attracted by mixture of Z3,Z13-18:Ac/OH in a ratio of 9:1, Pyropteron sp. n. by the same mixture (ratio 1:9), Bembecia romanovi and B. zuwandica by Z3,Z13-18:AC and E3,Z13- 18:Ac (9:1), Synanthedon caucasicum by the same mixture in the opposite ratio (1:9), B. scopigera by 23,213-18:Ac and E2,Z13-18:OH in a ratio 9:1, Synasphecia triannuliformis by Z3,Z13-18:OH and E3,Z13-18:OH (9:1), Similipepsis takizawai and Archimeessia sp. n. by E3,Z13-18:OH and E2,Z13-18:Ac (1:1), Prochoreutis sechestediana by a mixture of E3,Z13-18:Ac plus E2,Z13-18:OH (1:), Microsphecia brosiformis by E3,Z13-18:Ac, Synanthedon conopiformis by the analogous alcohol, Synanthedon scoliaeformis and Nemaxera betulinella by E2,Z13-18:Ac, Triaxomera fulvimitrella by Z3,Z13-18:Ac. An analogous alcohol com- ponent is essential for the attraction of B. ichneumoniformis males. In- hibitors for B. romanovi, B. scopigera and B. zuwandica attraction were discovered. Preliminary data on attractants for six other species as well as on the diurnal rhythm of sexual activity of three species are presented. A new method for the stereoselective synthesis of 3,13-18:Ac/OH and E2,Z13-18:Ac/OH is described.
Key Words--Lepidoptera, Sesiidae, Tineidae, Choreutidae, (E2,Z13)-octa- decadien-l-ol/acetate, 3,13-octadecadien-l-ol/acetate, isomers, stereoselec- tire synthesis, sex attractants, inhibitors, field trapping.
INTRODUCTION
At present, sex pheromones and attractants are known for about 1500-2000 moth species (Am et al., 1986). This number is, however, small when compared with the large number of species in the order Lepidoptera and is insufficient to solve chemotaxonomic or evolutionary problems in pheromone communication systems. Hence, the search for attractants aimed at finding new chemical sub- stances as well as the detection of new species with already known compounds remains of great importance.
The identification of sex attractants for clearwing species is equally likely to be of use in taxonomic research. Moths in this family are strong fliers, but are not captured by light traps and, consequently, are more difficult to collect than many other moth species. Many sesiids have limited distributions and appear to be relatively scarce. Thus, their attractants could be useful for both taxonomic and biological studies.
The main components of sex pheromones that have been identified from the females of sesiids are dienes with a chain length of 18 carbon atoms and unsaturation at the 13 as well as the 2 or 3 position (Tumlinson et al., 1974; Schwarz et al., 1983) and, possibly, a corresponding monoene with unsaturation at the same 13 position (Szrcs et al., 1985).
In the present paper we describe a new approach to the synthesis of some C~8 dienes and field screening trials with a number of these compounds carried out in Lithuania, Armenia, Azerbaijan, Turkmenistan, Ukraine, as well as in the far east of Russia.
METHODS AND MATERIALS
Chemicals. Four isomers of 3,13-octadecadienes with functional alcohol and acetate groups, one isomer of 2,13-octadecadien-1-oi and the corresponding acetate, as well as one monoene with equal carbon chain lengths were used for field screening (Table 1).
Synthesis and Purity. The steps for the synthesis of 3,13-octadecadien- 1-yl acetates and alcohols are shown in Figures 1 and 2. The methods for the synthesis of 3,13-octadecadienols are mainly based on the alkylation of metal- acetylides with protected 8-bromo-l-octanol (Uchida et al., 1978; Doolittle et al., 1980) or on the shift of the triple bond in 3-decyn-l-ol to the terminal position under superbasic media (Zhang et al., 1985; Teng and Yuan, 1985).
DIENE ATTRACTANTS
TABLE 1. C18 COMPOUNDS USED FOR SCREENING
801
Double Bond
position
Functional group and isomer
Ac OH
3,13 ZZ ZZ 3,13 EZ EZ
3,13 EE EE 3,13 ZE ZE 2,13 EZ EZ
13 Z Z
"'~'~/"~/'~OH "-~ ~i~s'~1~f" OH b
d
e
~ v ~ / ~ / ~ j ~ / ~ B r ~ W ~ - ' ~ ~ V ~ O H
W = V V - V ~ : ~ O H ~ N = ~ V V ~ OH
Z3, Z13 - 18 OH F__.3, Z13 - 18 OH
Z3, Z13 - 18Ac E3, Z13 - 18Ac
FIG. 1. Stereoselective synthesis of Z,Z- and E,Z-3,13-IS:OH/Ac. For a g abbreviations, see Figure 3.
Judging by the yields and complexity of reactions, preference is given to the latter method.
The triple-bond shift in ethylenediamine was undertaken with NaNH(CH2)2NHa at 25~ The reagent was obtained from NaNHa and ethyl- enediamine without specific removal of the ammonia formed. The key stage of the synthesis, namely, the reaction between the 9-tetradecenylhalide and tetra- hydropyranyl ether of 3-butyn-l-ol resulted in a relatively low yield of 35%, which agreed with previously published data, but not with the results presented by Hoskovec et al. (1990), where the yield of the product is indicated to be up to 65%. For E reduction of the triple bond in 9-tetradecyn-l-ol and 13-octa- decen-3-yn-l-ol, Rossi's method appeared to be appropriate (Rossi and Carpita,
8 0 2 Bf3DA ET AL.
1977). Preliminary data on the method of synthesis and the biological activity of (Z,Z) and (E,Z)-3,13-octadecadienols and their acetates were presented briefly by the present authors at the thirty-second IUPAC Conference (Miieorg et al., 1989).
(E2,Z13)-octadecadien-l-ol and the corresponding acetate were synthe- sized according to the scheme given in Figure 3.
The reaction control and the purity of products were determined by GLC with the chromatograph Chrom-5 using a glass column 2.5 m x 2 mm packed with 10% PDEAS on Chromosorb W-HP 100-120 mesh. The isomer compo- sition and the reduction control of the enynols were checked on a fused silica
' ~ = ~ O H '~- \ OH
$, $, Z3, E13 - 18Ac F_.3, E13 - 18Ac
FIG. 2. Stereoselective synthesis of Z ,E and E ,E isomers of 3 ,13 - | 8: OH/Ac. For c-g
capillary column 25 m • 0.2 mm coated with a liquid crystal p-methoxycin- namoyloxy-p'-methoxyazobenzol. The structure of products obtained was con- firmed by IR and 13C NMR spectroscopy with Spekord 711R and Bruker AC200P instruments, respectively. The isomer purity of E2,Z13-18 :Ac/OH was over 99% and that of E3,E 13-18:Ac/OH was 94.5 %, whereas purity of other iso- mers was lower.
Some of the E2,Z13-18:Ac was obtained from Dr. S. Voerman (Wag- eningen); its isomeric purity exceeded 99%. The compound was used at the initial stage of the screening program.
Z13-18:Ac/OH was synthesized according to Klun et al. (1975), the iso- meric purity exceeding 99 %.
Field Experiments. Each compound tested was dissolved in hexane and applied to red rubber tube dispensers (18 x 15 mm; a single cap for compound mixtures), 0.5 mg/cap. Each lure was fixed into an opaque white delta trap measuring 10 x 11 x 10 cm, which had an exchangeable bottom (11 x 18 cm) coated with sticky material (Atracon A trap and Pestifix glue, both from Flora Co., Tartu, Estonia). Traps were fixed to bush or tree branches 0.5-1 m above the ground and were inspected every one or two days or once a week depending on total screening duration. The distance between traps was not less than 15 m.
Screening was carded out from 1986 to 1991 in Lithuania and various areas of European and Asian territories of the former USSR. The trapping period as well as the number of traps in each locality are described below. For brevity, localities are numbered and indicated in the text and Table 2 as follows:
I--Lithuania: Ia, vicinity of Vilnius (eastern Lithuania), May 22 to July 24, 1986, two C18 compounds were tested separately (see Table 2), six repli- cates; Ib, the same locality, June 23 to July 29, 1987, five replicates of each attractant noted in Table 2; Ie, Puvo~iai, Varena District (southern Lithuania), July 22-27, 1990, two replicates.
II--Azerbaijan, vicinity of Lenkoran (southem Azerbaijan), August 4-9, 1987, seven replicates of separate components or mixtures noted in Table 2.
III--Armenia, the Khosrov Reserve (southwestern Armenia), July 10-19, 1989, four replicates.
IV--Turkmenistan: IVa, Kara-Kala, Parkhai (southwestem Turkmenistan), September 17-21, 1991, three replicates for each compound and each mixture; IVb, Syunt Khoserdag Reserve, Yol-Dere Canyon, May 5-17, 1989, four rep- licates; IVc, the same locality, September 3-15, 1989, five replicates.
V--Far east of Russia: Va, Kedrovaya Pad Reserve, Primorye, July 26 to August 12, 1989, four replicates; Vb, Partizansky District, Barabash-Levada, July 14-30, 1989, four replicates.
VI--Ukraine, Crimea, Karadag Reserve: Via, August 10-18, 1990, four replicates; VIb, July 4-14, 1991, three replicates.
Statistical Analysis. Data from the field tests were transformed x/x + 0.5
8 0 4 BI3DA ET AL.
where x is the number of moths captured per trap. Then they were submitted to analysis by Duncan's multiple-range test and significantly different means were separated.
Identification of Moth Species. Captured specimens were identified by anal- ysis of genitalia. Scientific names are given according to Leraut (1980) and Zagulyaev (1964) and descriptions of new species according to Gorbunov (1986, 1987) and Arita and Spatenka (1989). Bembecia ichneumoniformis and B. sco- pigera were identified after (;patenka and La~tuvka (1990), Microsphecia bro- siformis after La~tuvka (1985).
Representative specimens are kept in the insect collection at the Institute of Ecology, Vilnius, Lithuania.
RESULTS AND DISCUSSION
New sex attractants for 13 clearwing (Sesiidae), four tineid (Tineidae), and one choreutid (Choreutidae) moth species as well as inhibitors for three of the sesiids were found during the field screening trials. Detailed data are presented in Table 2. The following species were attracted:
Sesiidae
Microsphecia brosiformis Hubn. (= Zenodoxus dorsalis Le Cerf after Las- tuvka, 1985). A total of 42 males were captured: eight in Armenia (HI) and 34 in Turkanenistan (IVa,c). E3,Z13-18:Ac and two mixtures both containing 90 % of this component showed highest attractivity, which differed statistically significant from all tested compositions (Table 2). The binary mixtures were no more attractive than a single E3,Z 13-18:Ac, even tending to be less attractive; therefore, only E3,Z13-18:Ac should be considered a sex attractant for this species. Traps baited with this chemical are quite effective in trapping males.
It should be noted that during screening in Portugal the same substance was determined to be a sex attractant for M. tineiformis Esp., a very closely related species (Nielsen et al., 1979). This species and M. brosiformis were for a time considered synonymous (see Heppner and Duckworth, 1981) and only recently were they classified as two separate species (Lagtuvka, 1985). It is not quite clear if the sex attractants for both species are indeed the same. It is highly possible that moths trapped by Nielsen et al. (1979) could be classified as M. brosiformis following the latest morphological study (La~tuvka, 1985). For that reason, clearwings trapped to E3,Z13-18 :Ac in Portugal should be reinvesti- gated and their taxonomy verified. In case the representative specimens are no longer available, M. tineiformis sex attractant composition should, in our opin- ion, be reinvestigated.
Similipepsis takizawai Arita et Spatenka. A total catch of 34 males of the
DIENE ATTRACTANTS 805
species was obtained in the Far East (u Vb). Most moths (15) were attracted to a mixture of E3 ,Z13-18 :OH and E2 ,Z13-18 :Ac in a ratio of 1: 1. This is the first attractant blend for the genus and the first record of the species outside Japan.
Sesia yezoensis Hampson. Thirty-six males were trapped in the far east of Russia (Va, Vb). Most of them were attracted to a mixture of Z3 ,Z13-18:Ac and Z3 ,Z13-18 :OH in a ratio of 9 : 1 (Table 2). No attractivity was registered, when both components were tested separately or in different ratios.
Synanthedon caucasicum Gorbunov. Captures in Azerbaijan (II) totaled 145 males. The most attractive blend for them was that of Z3 ,Z13-18:Ac and E3,Z13-18 :Ac in a ratio of 1:9. Separately, the components were not attrac- tive, and only one moth was captured at baits with the main component E3,Z13- 18:Ac. Mixtures in other ratios were ineffective. When alcohol (E3,Z13- 18 : OH) is used in the mixture with E3,Z13-18 : Ac, the blend is also attractive, although significantly less than the two acetates. Thus, the E3,Z13 alcohol might be a syntergist; however, to determine this, tests with three-component mixtures should be made. It is noteworthy that S. caucasicum is morphologically very closely related to S. vespiformis L. (Gorbunov, 1986), as is the chemical composition of their sex attractants (the present paper and Voerman et al., 1983). Preference of the same attractant indicates that interspecific isolation is unlikely to be determined by differences in pheromone composition.
Our previous indication on S. caucasicum single-component attractant (M~ieorg et al., 1989) should be considered as preliminary. A two-component mixture for the attraction of males of this species is necessary.
Synanthedon conopiformis Esp. A total of 25 males were trapped in Lith- uania (Ib). Five binary mixtures of 13 used were attractive, the common com- ponent being E3,Z13-18 : OH. Of the compounds tested singly, only this alcohol was attractive. The total number of moths captured was small, as this species is scarce in the trapping area. Indeed, the species has been recently included in the Red Data Book (of rare species) of Lithuania. The attractant E 3,Z 13-18 : OH is effective enough for monitoring S. conopiformis populations, as was proved by our special program for monitoring this rare species throughout Lithuania, started in 1990.
Synanthedon scoliaeformis Borkh. In Lithuania (la) 174 moths were cap- tured in traps baited with a single component, E2,Z13-18:Ac. As it appeared to be an effective attractant, binary mixtures with other C18 dienes were not tested.
Pyropteron sp. n. Twenty-eight males were captured in traps baited with a mixture of Z3,Z13-18 :Ac and Z3 ,Z13-18 :OH in Turkmenistan (IVb). The most attractive blend for them was a ratio of 1 : 9. Three males were attracted to the mixture of the same alcohol and E2,Z13-18 :Ac in a ratio of 1 : 1.
Synasphecia triannuliformis Freyer. Seventy-three males were trapped in
TABLE 2. TRAP CAPTURES OF MOTHS WITH DIFFERENT C18 DIENES AND THEIR BINARY
I : l 9:1 1:9 I:1 la 9:1 1:9 9b 1:1 9:1 1:9 1:1 I:1 1:1 9:1 1:9 1:1 9:1 1:9
l : l la 9:1 i:9 lib 1:1 9:1 1:9 l : l
1:1 I : I 1:1
17b 1:1 9:1 la 1:9 1:1 1:1 2a 1:1 la 1:1 la
1:1 I : I l : l
42
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15b
34
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la 7b
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8 0 8 BUDA ET AL.
Armenia (Ill). They were attracted by Z3,Z13-18 : OH alone, as was previously shown by Sz6cs et al. (1989). However, attractivity increased almost threefold when combined with E 3,Z 13-18 :OH at a ratio of 9:1 (difference is statistically significant at P < 0.05). Almost all binary mixtures tested, which contained Z3,Z 13-18 : OH, were attractive for males of this species; therefore, an obvious inhibitor cannot be determined. Sexual activity of S. triannuliformis males was observed in the evening before sunset (two moths were attracted to traps between 8:15 and 8:40 PM).
Bembecia romanovi BarteU. Forty-eight males were trapped in Armenia (HI). They were mostly attracted by a mixture ofZ3,Z13-18 :Ac and E3,Z13- 18"Ac in a ratio of 9:1. The ZZ isomer alone was also a good attractant, although the capture decreased almost by half (Table 2). The EZ isomer did not attract any males when applied individually. Captures of B. romanovi males with Z3,Z 13-18:Ac as the main attractant component were strongly inhibited by Z3,Z13-18:OH. Their mixtures did not attract a single moth. A less pro- nounced inhibitor for males of the species was E3,Z13-18: OH; only one male was trapped when the compound was added to Z3,Z13-18:Ac. It should be noted that both inhibitors differ from the attractant components only by the functional group (alcohol).
It is interesting that a melanic form, previously undescribed, was trapped together with the typical golden form of B. romanovi males. Melanic individuals comprised 13.3 % of the total catch. There were no significant differences between their preferences for attractants.
Males appeared to be attracted to the traps in the morning. Captures were registered between 9:20 and 10:00 AM (based on six males).
Bembecia ichneumoniformis Den. et Schiff. (sensu Spatenka and Lastuvka, 1990). Twenty-six months were trapped in Armenia (III), of the 26 males trapped with different compositions, most were attracted to three mixtures all containing the same component, namely Z3,Z13-18:OH (Table 2).
The alcohol is significantly less attractive than binary mixtures with either E3,Z 13-, E2,Z 13- or Z3,Z 13-acetates, which indicates that an acetate admix- ture increases the attractivity of the alcohol. However, we could not determine which of the three acetates was most effective, because the differences were not statistically significant due to the small number of replicates (four) and short period of trapping (10 days). Therefore, to optimize the attractant composition, attempts should be made to find a coattractant among the acetates.
Bembecia scopigera (Scopoli), sensu Spatenka and Lastuvka (1990). One hundred eighty-three males were trapped in the Crimea (Via,b). Males were attracted to traps baited with Z3,Z13-18:Ac alone, as well as to 11 different binary mixtures containing this chemical. It proved to be an effective attractant; however, the highest attractivity was observed for lure containing Z3,Z13- 18:Ac and E2,Z13-18:OH at a ratio of 9:1 (Table 2). The effectiveness of
DIENE ATTRACTANTS 809
the mixture was significantly higher compared to that of all mixtures tested; therefore, it should be considered the optimal attractant for B. scopigera males.
Admixture of E3,Z 13-18:Ac (in a 1:1 ratio) to Z3,Z 13-18:Ac, the main component of the attractive blend, which is also effective when applied singly, is fully inhibiting to B. scopigera male capture, so this acetate is potential inhibitor of the most effective attractant blend.
It is interesting to note that although E2,Z13-18: OH was found in phero- mone glands of clearwings (Klun et al., 1990), there have so far been no indi- cations that it could modify males' behavior.
According to the screening data obtained in Hungary, the attractant deter- mined for B. scopigera males was Z3,Z 13-18:OH (Sz6cs et al., 1989). Authors of the publication mentioned consider B. scopigera to be synonymous to B. ichneumoniformis, although both taxa have obvious morphological differences and are classified as separate species (Spatenka and La~tuvka, 1990). The data we obtained on differences in the sex attractant composition for both taxa also indicate them to be two separate species.
B. scopigera specimens trapped in Hungary are no longer available (Szfcs, personal communication); therefore, it is impossible to reinvestigate their gen- italia. In our opinion, clearwings trapped in Hungary and considered as B. scopigera should be attributed to B. ichneumoniformis (sensu Spatenka and La~tuvka, 1990).
Bembecia puella Lastuvka. In the Karadag Reserve, Crimea, (Via,b) 52 males were trapped. Most of them (32) were attracted to traps with a mixture of Z3,Z13-18 :Ac and Z3,Z13-18 : OH at a 9:1 ratio. Attractivity to the mix- ture is highest (Table 2). The same mixture at a 1 : 1 ratio trapped B. puella males, but significantly fewer. Separate components of the mixture were not effective.
Bembecia zuwandica Gorbunov. Thirty-seven males were trapped in Armenia (liD. Most males were trapped by a mixture of Z3,Z13-18:Ac with E3,Z13-18:Ac at a ratio of 9:1 (Table 2). A single Z3,Z13-18:Ac also appeared to be attractive for males of this clearwing species. The alcohol E3,Z13-18:OH, which corresponds to the minor attractant component with an acetate functional group, appears to be an inhibitor for this species. It fully inhibited attractivity of Z3,Z13-18:Ac (Table 2).
Males were trapped in the late morning between 10:05 AM and 12:45 PM (based on 22 males).
It is interesting to note that B. zuwandica males are attracted to the same mixture and at the same habitat as B. romanovi. Although our observations were based on attmctants only, and the actual pheromone blends for the two species could differ slightly, we can assume that the difference in the diumal rhythm of sexual activity is of great importance for the interspecific isolation of B. zuwan- dica and B. romanovi. However, their activity periods overlap slightly; there-
8 1 0 BUDA ET AL.
fore, additional isolating mechanisms, e.g., either behavioral, morphological, etc., might be involved.
Trapping data for the remaining sesiid species are not presented in Table 2 as they are either preliminary or only confirm some preliminary data obtained earlier by other authors.
Syrumthedon culiciformis L. In Lithuania (Ia), 179 males were trapped using Z3,Z13-18:Ac as bait. It appeared to be a good attractant, and no tests with other potential synergists were undertaken. Our results confirm the data of Fassotte et al. (1986), which are considered as preliminary by Am et al. (1986).
Screening in Armenia ( l id and Turkmenistan (IV) provided data on sex attractants for another five clearwing species. For a number of reasons, captures of these species were low, so the data can be considered only as preliminary.
Bembecia parthica Led. Five males were captured by traps baited with a mixture of Z3 ,Z13-18:Ac and the corresponding alcohol during a three day period. The mixture was more effective at a ratio of 9 : 1 in I I I .
Bembecia chalciformis Esp. Sixteen males were attracted and trapped in I I I and IVb by six different binary mixtures containing Z3,Z13-18:OH. This compound was unattractive when used singly and effective in a mixture with two acetates. Admixture of Z3,Z13-18:Ac was effective in Turkmenistan (11 males) and admixture of E3,Z 13-18:Ac attracted moths in Armenia (five males).
Chamaesphecia affinis Staud. Five males were trapped in I I I , four at a mixture of the diene-monoene E3,Z13-18 :Ac and Z13-18 :OH in a ratio of 1 : 1~ Individual components were not attractive. One male was attracted to a mixture of E3,Z13-18 : Ac and Z3,Z13-18:OH.
Chamaesphecia sp. n. Eight males were trapped in Turkmenistan (IVb), all in two traps with a mixture of E3,Z 13-18:Ac and E2,Z 13-18:Ac in a 1:1 ratio.
Zenodoxus hoplisiformis Mann. Seven males were trapped in I I I . A mix- ture of E3,Z 13- t8 :Ac and E2,Z 13-18:Ac appeared to be most attractive at a ratio of 1 : 1. Two males were captured at a mixture containing the same first component and E2,Z13-18:OH.
Tineidae
Archimeessia sp. n. In the Far East, 260 males were trapped at the mixture of E3 ,Z13-18 :OH and E2,Z13-18:Ac at a ratio of 1:1 (Table 2). All other lures were not attractive. This is the first report of Archimeessia tineids captured with synthetic sex attractants.
Tiaxomera fulvimitrella Sod. In Lithuania (Ia), 110 males were captured (see Table 2) with Z3,Z13-18 :Ac alone. Mixtures with other components were not tested.
Nemaxera betulinella F. ( :cor t icel la Curt.). Fifty-seven males of this spe- cies were trapped in Lithuania (Ia), at E 2 , Z I 3 - 1 8 : A c alone (Table 2).
DIENE ATTRACTANTS 81 1
Nemapogon flavifrons Pt. In Turkmenistan (IVb,c) 396 moths were trapped. A mixture of Z3 ,Z13-18:Ac with a corresponding alcohol in a ratio of 9:1 was the best attractant. When applied singly, the first component was attractive, although considerably less as compared to the binary mixture, whereas the attractivity of the second component was not registered (Table 2).
We obtained data on the sex attractant for another tineid species Nemapogon clematella F. (= arcellus F.). In Lithuania (Ia), 182 males were trapped with Z3,Z13-18:Ac. This confirms the data of Fassotte et al. (1986), which are considered as preliminary by Am et al. (1986).
In Russia's far east (Vb), 33 males of tineid Celestica angustipennis H.-S. were attracted to the blend of E3,Z13-18:OH and E3,E13-18:Ac at a ratio 1 : 1. All moths were caught in only two traps of 4 with the same mixture applied. Therefore, the result should be viewed as preliminary only. It is inter- esting to note that this species, traditionally considered an inhabitant of Europe and western Asia, was traced in the Far East, which indicates its habitat to be very wide indeed, from the Atlantic in the west to the Pacific in the east.
The presence of dienic alcohols in the attractant blend for N. personellus (Sz6cs et al., 1989) as well as for N. flavifrons, T. fulvimitrella, and apparently for C. angustipennis (data of the present paper) suggests that they are as common in the family as the acetates (see Am et al., 1986).
Choreutidae
Prochoreutis sehestediana F. (= punctosa Hw.). Forty-one males were trapped in Lithuania (Ic). Most males were trapped by a mixture of E3,Z13- 18:Ac and E2,Z13-18 :OH at a ratio of 1 : 1 (Table 2). The alcohol in a mixture with either Z3,Z13-18 : Ac or a corresponding alcohol (at a 1 : 1 ratio) is slightly attractive (Table 2). Captures of the species were low due to very unfavorable weather conditions: during the whole trapping period only two days were without rain.
The present report on sex attractant composition for P. sehestediana males is the first recording within the Choreutidae family; another species of the family is attracted by a mixture of (E2,Z13)-octadecadienol/acetate, as was demon- strated using chromatographically purified chemicals (Bfida and Schwarz, in preparation).
It is noteworthy that the similarity in attractant composition within the Sesiidae and Choreutidae families is not accidental. Taxonomically both families are closely related and belong to the same superfamily Sesioidae. A much more complicated question is the relatedness of the families Sesiidae and Choreutidae to Tineidae. Namely, is the similarity in the attractant (pheromone) chemical composition between the latter family and Sesiidae/Choreutidae completely acci- dental?
812 BODA ET AL.
T h e resul ts ob ta ined on the h igh s imi lar i ty in the a t t rac tant c o m p o s i t i o n for
m o t h s o f Ses i idae and Chor eu t i dae fami l ies sugges t tha t these or ve ry s imi la r
c o m p o u n d s could be ef fec t ive sex a t t rac tants for the Brachod idae fami ly as well ,
b ecause all th ree fami l ies are c lass i f ied as one super fami ly .
Acknowledgments--We thank Dr. O. Gorbunov (Institute of Animal Evolutionary Morphology and Ecology, Moscow) for help in the identification of several clearwing species and consultations. The assistance of Mrs. Lea Talu in the synthesis of Z 13-18 : OH/Ac and biologists J. Miatlieuski, P. Stepanauskas, D. Stitilis, and G. Svitra in field work as well as V. Merraitis in the statistical analysis, and Giedr6 Kapturauskien6 in preparing the English version of an early draft of the paper is gratefully acknowledged.
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