Induced Maturation and Spawning by Sex Pheromones in Female Mudskipper (Boleophthalmus pectinirostris)

Maturation of the 4th phase oocytes of mudskipper is induced in vitro by sexpheromones,the extract of ovary,testis and seminal vesicle,oxytocini and deoxycorticosterone(DOC).Maturation rates of oocytes are related to pheromones and their dosages.The single use ofprostaglandin E_1(PGE_1)is not effective in the induction oi maturation,but the combination ofPGE_1 with HCG promotes oocyte maturation rates.Maturation is induced by injections of the extractof the ovary at dosages of 0.01 cm^3/a fish,seminal vesicle extract at dosages of 0.1 cm^3/a fish,testis extract at dosage of 0.1 cm^3/a fish,or PGE_1 at dosage of 10μg/fish,respectively.Amongthem,seminal vesicle extract is the most effective in the induction of maturation.The artificialnests,with the extract of the ovary,testis or seminal vesicle inside,attract more heterosexualmudskippers than homosexual mudskippers to enter.Especially,the extract of seminal vesicle is themost effective in attracting females.Female mudskippers could be induced to spawn by the extractsof ovary,testis and seminal vesicle placed inside both the ceramic and sponge nests.More spawnedeggs and higher fertilization rates are observed in the ceramic nests than in the sponge ones.

Identification of Female Main Component Sex Pheromones of Orthaga achatina(Lepidoptera:Pyralidae) and Their Attractiveness to Moths

[Objective] The aim is to identify the composition of female sex pheromones of Orthaga achatina and to understand the differential attractiveness of these components to Orthaga achatina moths. [Method] The pheromone glands of female moths were extracted and analyzed using gas chromatography coupled with mass spectroscopy（GC-MS）; the chemical analysis was confirmed by electroantennogram（EAG） bioassays; a field trial was conducted to confirm the optimized blends. [Result] Z11-16：Ac could elicit the largest EAG responses in male moths at all the doses tested. EAG responses to plant volatiles and to the pheromone isomers of Z11-16：Ac were at a similar level and lower than the responses to Z11-16：Ac. In the field tests, it was demonstrated that synthetic Z11-16：Ac was significantly more attractive to male O. achatina moths, that its pheromone isomers, whether these were presented alone or in mixtures with Z11-16：Ac. [Conclusion]（Z）-11-hexadecenyl acetate（Z11-16：Ac） was identified as the main component of the sex pheromone and it was demonstrated that synthetic Z11-16：Ac was significantly more attractive to male O. achatina moths.

Control Effect and Cost Evaluation of Different Sex Pheromones and Trapping Lamps against Spodoptern litura,Helicoverpa assulta and Helicoverpa armigera in Tobacco

[ Objective] The aim was to study the control effect of different sex pheromones and trapping lamps against main pests in tobacco. [ Method] Control effect of sex pheromone of different matrix lures and Jiaduo trapping lamp against Spodoptern litura, Helicoverpa assulta and Helicoverpa armigera in tobacco in Teng- chong of Yunnan were determined and compared, and the control cast was evaluated. [Result] The use of insect sex pheromones and insecticidal light traps had certain effect against S. litura and H. armiger. The trapping effect of sex pheromone traps was better than that of Jiaduo trapping lamp, and the PVC matrix lure had better performance than rubber matrix lure, which had strongest capturing capacity, continuous control effect and significant effort against S. litura. The traps with different settled densities and hanging heights also had different trapping effect against S. litura and H. armiger, and the hanging height of 100 - 150 cm from ground was the best; as the cost was considered, the cast of the area with low density of traps was the lowest, which was reduced by over 44% than conventional chemical control area. [ Conclusion] It is safe and effective to use sex pheromone and insecticidal light traps to control S. litura and H. armigera, and it is a green environmental protection biological physical control technology, having extended application prospect in large area.

Identification of an odorant receptor responding to sex pheromones in Spodoptera frugiperda extends the novel type-I PR lineage in moths

moths,pheromone receptors(PRs)are crucial for intraspecific sexual communication between males and females.Moth PRs are considered as an ideal model for studying the evolution of insect PRs,and a large number of PRs have been identified and functionally characterized in different moth species.Moth PRs were initially thought to fall into a single monophyletic clade in the odorant receptor(OR)family,but recent studies have shown that ORs in another lineage also bind type-I sex pheromones,which indicates that type-I PRs have multiple independent origins in the Lepidoptera.In this study,we investigated whether ORs of the pest moth Spodoptera frugiperda belonging to clades closely related to this novel PR lineage may also have the capacity to bind type-I pheromones and serve as male PRs.Among the 7 ORs tested,only 1(SfruOR23)exhibited a male-biased expression pattern.Importantly,in vitro functional characterization showed that SfruOR23 could bind several type-I sex pheromone compounds with Z-9-tetradecenal(Z9-14:Ald),a minor component found in female sex pheromone glands,as the optimal ligand.In addition,SfruOR23 also showed weak responses to plant volatile organic compounds.Altogether,we characterized an S.frugiperda PR positioned in a lineage closely related to the novel PR clade,indicating that the type-I PR lineage can be extended in moths.

Moth sex pheromones affect interspecific competition among sympatric species and possibly population distribution by modulating pre-mating behavior

Premating behaviors mediated by pheromones play pivotal roles in animal mating choices.In natural populations of the striped stem borer Chilo suppressalis and the rice leaf roller Cnaphalocrocis medinalis in the rice field habitat,we discovered that Z11-16:Ald,a major component of the C.suppressalis pheromone,modulated the premating behavior of C.medinalis.Z11-16:Ald evoked a strong olfactory response in male antennae and strongly inhibited the sex pheromone trapping of male C.medinalis in the field.The functions of three C.medinalis sex pheromone receptor genes(CmedPR1–3)were verified through heterologous expression in Xenopus oocytes.CmedPR1 responded to Z11-18:OH and Z11-18:Ald,as well as the interspecific pheromone compound Z11-16:Ac of sympatric species;CmedPR2 responded to Z13-18:OH and Z13-18:Ald,as well as the sex pheromone compounds Z11-16:Ald and Z9-16:Ald of sympatric species;and CmedPR3 responded to Z11-18:OH and Z13-18:OH,as well as the interspecific pheromones Z11-16:OH,Z9-16:Ald,Z11-16:Ac,and Z11-16:Ald of sympatric species.Thus,CmedPR2 and CmedPR3 share the ligand Z11-16:Ald,which is not a component of the C.medinalis sex pheromone.Therefore,the sex pheromones of interspecific species affected the input of neural signals by stimulating the sex pheromone receptors on the antennae of male C.medinalis moths,thereby inhibiting the olfactory responses of the male moths to the sex pheromones.Our results demonstrate chemical communication among sympatric species in the rice field habitat,the recognition of intra-and interspecific sex pheromones by olfactory receptors,and how insect premating behaviors are modulated to possibly affect resource partitioning.

The Ca^(2+)/CaN/ACC and cAMP/PKA/HK signal pathways are required for PBAN-mediated sex pheromone biosynthesis in Conogethes punctiferalis

Conogethes punctiferalis is a crop and fruit pest that has caused serious economic losses to agricultural production.This pest relies heavily on its sex pheromone to ensure sexual encounters and subsequent mating success.However,the molecular mechanism underlying sex pheromone biosynthesis in this species remains elusive.The present study investigated the detailed mechanism underlying PBAN-regulated sex pheromone biosynthesis in C.punctiferalis by transcriptome sequencing of the C.punctiferalis pheromone glands(PGs)and subsequent functional identification of the target genes.The results showed that female mating started from the first scotophase,and peaked at the second to fifth scotophases in accordance with the release of sex pheromones.PBAN regulated sex pheromone biosynthesis by employing Ca^(2+)and cAMP as secondary messengers,as demonstrated by RNA interference(RNAi),pharmacological inhibitors,and behavioral assays.Further investigation revealed that calcineurin(CaN)and acetyl-CoA carboxylase(ACC)were activated by PBAN/Ca^(2+)signaling,and the RNAimediated knockdown of CaN and ACC transcripts significantly reduced sex pheromone production,ultimately leading to a significantly reduced ability of females to attract males.Importantly,hexokinase(HK)was found to regulate sex pheromone biosynthesis in response to the PBAN/cAMP/PKA signaling pathway,as demonstrated by RNAi,enzyme activity,and pharmacological inhibitor assays.Furthermore,Far2 and Desaturase1 were found to participate in PBAN-regulated sex pheromone biosynthesis.Altogether,our findings revealed that PBAN regulates sex pheromone biosynthesis through the PBANR/Ca^(2+)/CaN/ACC and PBANR/cAMP/PKA/HK pathways in C.punctiferalis,which enriches our comprehension of the details of sex pheromone biosynthesis in moths.

The evolution of female sex pheromones

The role of female sex pheromones in natural selection, particularly as a means for species recognition to avoid the generation of hybrid offspring with low fitness, has been widely explored and is generally accepted by scholars. However, the significance of sex pheromones in shaping mate choice （sexual selection） and in competition over breeding resources （social se- lection） has been largely ignored. The effect of sexual selection on sex pheromones as a sexually dimorphic signaling trait has been discounted because the amount of pheromone released by females is typically minute, while the role of sex pheromones in competition over breeding resources （other than mates） has not yet been considered. As a result of natural selection, variation in sex pheromones among females is expected to be low, and males are not expected to choose their mates among phero- mone-releasing conspecific females. Sexual selection, on the other hand, should drive the increase in pheromone variance among females, and males are expected to choose females based on this variation. Moreover, social selection resulting from more general social interactions, for example competition among females for breeding sites and food, should also promote variance among female sex pheromones. Here, we review the cttrrent evidence for each of the three selection processes acting on sex pheromones of female moths as an advertising trait. We suggest that the three selection types are not mutually exclusive but rather act together to promote different fimess components in diverse ecological situations

Analysis of sex pheromone production and field trapping of the Asian corn borer(Ostrinia furnacalis Guenée)in Xinjiang,China

Identifying the sex pheromone systems of local pest populations facilitates their management,especially for moth species that show significant geographic variation in sex pheromone communication.We investigated the pheromone production and behavioral responses of the Asian corn borer(Ostrinia furnacalis Guenée;ACB)in Xinjiang,China.The ACB produces three compounds:(Z)-12-tetradecenyl acetate(Z12-14:Ac)and(E)-12-tetradecenyl acetate(E12-14:Ac)which are two sex pheromone compounds,and n-tetradecyl acetate(14:Ac)which has variable roles in mediating behavioral responses.The ratios of these three compounds produced in female gland are geographically distinct among different populations.Quantitative analysis of pheromone production showed that the proportions of Z12-14:Ac in the E/Z isomers(i.e.,Z and E12-14:Ac)and the proportions of 14:Ac in the ternary blend respectively averaged 60.46%(SD=5.26)and 25.00%(SD=7.37),with their probabilities normally or near-normally distributed.Trapping experiments in a cornfield indicated that deploying the E/Z isomers and the three compounds in rubber septa close to their gland ratios yielded the most captured males,while other ratios that deviated from the gland ratios showed reduced field captures.The ternary blend was significantly more attractive to males than the E/Z isomers in the field,indicating a functional role of 14:Ac as the third pheromone component used by the local population.Additionally,the dose-response test demonstrated that the application of the three compounds at dosages between 200 and 350μg attracted significantly more males compared to other dosages.Therefore,the characterization of this local ACB pheromone system provides additional information about its geographic variation and serves as a basis for optimizing the pheromone-mediated control of this pest in Xinjiang.

Development of a high-efficiency sex pheromone formula to control Euproctis pseudoconspersa

The tea tussock moth(Euproctis pseudoconspersa)is one of the most destructive chewing pests in tea plantations and causes a serious allergic reaction on the skin of tea plantation workers.The sex pheromone components of its Japanese population were first identified as 10,14-dimethylpentadecyl isobutyrate(10Me14Me-15:iBu)and 14-methylpentadecyl isobutyrate(14Me-15:iBu),with a stereogenic center.Only 10Me14Me-15:iBu has been identified in the Chinese E.pseudoconspersa population.However,field tests have shown that 10Me14Me-15:iBu cannot meet the demand of effective pest control in China.To develop a high-efficiency E.pseudoconspersa sex pheromone formula,electroantennogram(EAG)recordings of(S)-and(R)-enantiomers of 10Me14Me-15:iBu and 14Me-15:iBu were obtained in the present study.The results demonstrated that the EAG responses of male antennae to(R)-enantiomers were significantly higher than responses to the(S)-enantiomers,and 14Me-15:iBu also elicited EAG activity.Field tests showed that the catch numbers of male moths by(R)-enantiomers were significantly higher(P<0.05)than those of(S)-enantiomers.Addition of 14Me-15:iBu significantly increased the catch numbers of both the(S)-and(R)-enantiomers.The efficient pheromone formula containing 0.75 mg(R)-10Me14Me-15:iBu and 0.1 mg 14Me-15:iBu showed significantly higher attractiveness than commercial pheromone products.Our study demonstrated that(R)-10Me14Me-15:iBu was the major sex pheromone component of E.pseudoconspersa,and 14Me-15:iBu might be the minor sex pheromone component.Furthermore,a high-efficiency sex pheromone formula for E.pseudoconspersa control was defined in this study.

Sex Pheromone Components of the Female Black Cutworm Moth in China: Identification and Field Trials

The sex pheromone blend of a China strain of the black cutworm moth Agrotis ypsilon （Rottemberg） （Lepidoptera： Noctuidae） was investigated. Chemical analysis of pheromone gland extracts of 3-day-old females showed that individual isolated glands contained only very small amounts of pheromone. The high-resolution gas chromatography combined with mass spectrometry （GC-MS） analysis showed the presence of Cis-7-dodecenyl acetate （Z7-12：Ac, A）, Cis-9-tetradecenyl acetate （Z9-14：Ac, B）, Cis- 11-hexadecenyl acetate （Z 11 - 16 ：Ac, C）, Cis-8-dodecenyl acetate （Z8-12：Ac, E） and Cis-5-decenyl acetate （Z5-10：Ac, D） in biologically active pheromone gland extracts. An extract of one gland from a day 3 female gave the following values for the gland components： 0.245±0.098ng for Z7-12：Ac, 0.080±0.031ng for Z9-14：Ac, 0.089±0.033ng for Z11-16：Ac, 0.085±0.031ng for Z5-10：Ac, 0.105±0.065ng for Z8-12：Ac per female. The percentages of Z7-12：Ac, Z9-14：Ac, Z11-16：Ac, Z5-10：Ac and ZS-12：Ac in pheromone gland extracts from individual females were （meaniSE） 40.451±13.66, 13.176±5.279, 14.943±5.142, 14.392±6.10 and 17.225±9.792 respectively, and the percentages of Z7-12：Ac, Z9-14：Ac and Z11-16：Ac were 58.75±9.429, 18.91±7.539 and 22.34±7.209. Field trials indicated that each single component of sex pheromone was non-effective and captured no males. The lures baited with duality compound of AB （3 ： 1） had a certain attraction to males, the mean captured number was 2.6. The attraction ability of the lures baited with ternary compound of ABC （3 ： 1 ：1） to males added significantly, the mean captured number per trap was 7.40, which was 2.8 times of duality compound of AB （3 ： 1）. The contents of sex pheromone could obviously affect its capture ability to males, the mean captured number was the highest at the dosage of 200 μg.

SYNTHESIS OF 3,7-DIMETHYL-2-TRIDECANYL ACETATE--Active Component of Sex Pheromone of Pine Sawfly Diprion pini

The total synthesis of 3,7 dimethyl 2 tridecanyl acetate,the active component of the sex pheromone of diprion pini,was investigated in this paper.The two key synthins blocks,2 methyl octan 1 yl lithium and 3,4 dimethyl γ butyrolactone,were obtained from diethyl malonate and 2,3 epoxybutane.2 Methyl octan 1 yl lithium reacted with 3,4 dimethyl γ butyrolactone to yield the ketoalcohol and then followed by Huang Minlong reduction to afford 3,7 dimethyl 2 tridecanol,acylated with acetic anhydide to give 3,7 dimethyl 2 tridecanyl acetate.

Integrated Assessment of Trapping Efficiency of Colored Sticky Cards and Sex Pheromone on Liriomyza spp.and Plutella xylostella

[Objective] To evaluate the control effect of yellow sticky cards and sex pheromone on Plutella xylostella and Liriomyza spp.,which can provide reference for large area extension of the technique.[Method] The integrated assessment of trapping efficiency of colored sticky cards and sex pheromone on Liriomyza spp.and Plutella xylostella was conducted by field surveys and structured interview in Tonghai County,Yunnan Province,China.[Result] The results showed that yellow sticky cards and sex pheromone have strong power of trapping Liriomyza spp.and Plutella xylostella（3 414±720 and（219±157） head/piece,respectively）;the control cost by the usage of pesticide is the highest,（10 099.5±2 752.5） yuan/hm^2,yellow sticky cards and sex pheromone takes the second place,（1 125.0±465.0） yuan/hm^2,the control cost by the usage of yellow sticky cards is the lowest,（450.0 ±186.0）yuan/hm^2.Without the usage of yellow sticky cards and sex pheromone,pesticide application times and costs are（15.0±2.7） times and（12 070.5±2 136.0） yuan/hm^2;combined with usage of yellow sticky cards and sex pheromone,pesticide application times and costs reduce by 5.7 times and 4 618.5 yuan/hm^2.The ratio of trapped beneficial insects and target pests was 1 ∶1 131,which showed that the negative effect of yellow sticky cards and sex pheromone on the non-target insects was very limited.[Conclusion] The trapping approach has become popular among all the local farmers.Looking at the above factors,the trapping technology has strong application prospect and promotion value in pest control field.

Control of Tobacco Cutworm Moth Spodoptera litura Fabricius (Lepidoptera,Noctuidae) by Sex Pheromone Trapping Technology

[Objective] The paper was to promote using synthetic sex pheromone lures to control tobacco cutworm moth（Spodoptera litura Fabricius） .[Method] Three layers of pheromone traps for S.litura were set in the field at the density of 26 m×26 m（one trap/676 m2） to carry out field control test.[Result] The amount of egg massed reduced by 62.16% after trapping by sex pheromone under the density,and the larvae population was equivalent to those in the conventional control field with pesticides,the control effect was continuous,stable and significant.The larger the control area was,the better the effect was.[Conclusion] Using sex pheromone could effectively control S.litura and reduce pesticide usage for over 80% with economic,safe and efficient features,which should be incorporated into the technical control system of S.litura.

EAG and behavioral responses of Helicoverpa armigera males to volatiles from poplar leaves and their combinations with sex pheromone

Electroantennogram (EAG) evaluation of selected compounds from wilted leaves of black poplar, Populus nigra, showed that phenyl acetaldehyde, methyl salicylate, (E)-2-hexenal elicited strong responses from male antennae of Helicoverpa armigera. When mixed with sex pheromone (Ph), some volatiles, e.g. phenyl acetaldehyde, benzyl alcohol, phenylethanol, methylsalicylate, linalool, benzaldehyde, (Z)-3-hexenol, (Z)-3-hexenylacetate, (Z)-6-nonenol, cineole, (E)-2-hexenal, and geraniol elicited stronger responses from male antennae than Ph alone. Wind tunnel bioassay demonstrated that various volatiles could either enhance or inhibit the effect of synthetic sex pheromone. (E)-2-hexenal, (Z)-3-hexenol and linalool in combination with Ph could not induce any male to land on source at all, whereas phenyl acetaldehyde, benzaldehyde, (Z)-6-nonenol and salicylaldehyde combined with Ph enhanced male response rates by 58.63%, 50.33%, 51.85% and 127.78%, respectively, compared to Ph alone. These results suggested that some volatiles shouldmodify sex pheromone caused behavior and that some of them could possibly be used as a tool for disrupting mating or for enhancing the effect of synthetic sex pheromone in the field.

Progress on Sex Pheromone Synthesis of Asian Corn Borer, Ostrinia furnacalis (Guenee)

The progress on the components identification, synthesis methods （syn- thetic strategy of carbon chain increasing and synthetic strategy of carbon chain de- creasing） of Asian corn borer （Ostrinia fumacalis （Guenee）） sex pheromone was reviewed, which will provide a reference for the control of Asian corn borer.

A larval specific OBP able to bind the major female sex pheromone component in Spodoptera exigua(Hübner)

Odorant binding proteins （OBPs） in insects are postulated to solubilize and transport the hydrophobic odorants across the hydrophilic antennal lymph to the olfactory receptors （ORs） located on the dendrite membrane of the sensory neurons. OBPs in adult insects have been intensively reported, but those in larvae are rarely addressed. In our study, a full-length OBP cDNA, namely SexiOBP13, was cloned by RT-PCR and RACE strategy from the heads of Spodoptera exigua larvae. The quantitative real-time PCR （qPCR） measurement indicated that SexiOBP13 was highly expressed in larval head, but very low in other parts of larva and was not detected in any tissues of adult. The binding affinities of SexiOBP13 to plant volatiles and female sex pheromone components were measured by competitive binding assays. Interestingly, SexiOBP13 displayed a high binding affinity （Ki=3.82 IJmol L-1） to Z9,E12-14：Ac, the major sex pheromone component of S. exigua, while low affinities to the tested host plant volatiles （Ki〉27 μmol L-l）. The behavioral tests further confirmed that Z9,E12-14：Ac was indeed active to elicit the behavioral activity of the third instar larvae of S. exigua. Taken together, our results suggest that SexiOBP13 may play a role in reception of female sex pheromone in S. exigua larvae. The ecological significance of the larvae preference to the adult female sex pheromone was discussed.

A Facile Synthetic Method for (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene,Sex Pheromone Component of Hyphantria Cunea (Drug)

Total synthesis of (3Z, 6Z, 9S, 10R)-9, 10-epoxy-3, 6-heneicosadiene, sex pheromone component of Hyphantria cunea (Drug), was achieved using Sharpless AE kinetic resolution and alkylative epoxide rearrangement as key steps.

Optimization of the sex pheromone-based method for trapping field populations of Phthorimaea operculella(Zeller)in South China

Despite the identification of the potato tuber moth Phthorimaea operculella(Zeller)sex pheromone,no effective application based on this pheromone has yet been developed and evaluated.This study investigated the effect of pheromone lures,trap densities,heights of trap deployment,and pheromone doses in Yunnan,China,for the purpose of increasing the control efficiency of P.operculella and improving the application of pheromone technology in the field.The results showed that lures made of corn oil and red PVC pipes attracted the highest number of moths(11.73±1.90 per trap per day).Sex pheromone loading of 100μg was optimal for trapping moths,but higher doses of pheromone inhibited attraction.The density of traps did not affect capture rates;therefore,the optimum trap density was 30–40 traps ha^(–1).The optimum height of trap deployment was not above the height of the plant canopy.This study provides technical details necessary for the monitoring and control of potato tuber moth using sex pheromones.

Suppression of Rice Stem Borer, Chilo suppressalis by Mass Trapping Using Synthetic Sex Pheromone in Paddy Field

Suppressing effects of mass trapping using synthetic sex pheromone with main active ingredients of Z-11-hexadecenal, Z-13-octadecenal and Z-9-hexadecenal on the rice stem borer, Chilo suppressalis were investigated during the flight periods of the overwintering and 1st generation in the paddy area of 60 ha in 1999. Population density of C. suppressalis in the pheromone-treated fields was lower than that in control. The egg masses decreased by 74.39% and population size of adult males of the 1st generation decreased by 61.64% in the treated fields as compared to control. Meanwhile, the damage by C. suppressalis larvae was significantly lower in the treated fields than control (t-test, P=0.05). Percentages of brownish leaf sheath, dead heart, and white head in the treated fields were decreased by 70.90%, 57.01% and 44.30%, respectively in contrast to control. The present study demonstrated that mass trapping to C. suppressalis using synthetic sex pheromone shows great potential as an alternative measure in an environment-friendly pest management and at the same challenging the insecticide use that has some environment impacts.

Synergic effect of sex pheromone(7R,8S)-cis-7,8-epoxy-2-methyloctadec-17-ene on(+)-disparlure of the Asian gypsy moth,Lymantria dispar, in Korea

field attraction test of (7R,8S)-cis-7,8-epoxy-2- methyloctadec-17-ene (= 7R,8S-epo-2me-17ene-18Hy), a trace component of the sex pheromone gland of the Asian gypsy moth,(Lymantria dispar), traps that were baited with the trace component attracted more L. dispar than traps baited with (7S,8R)-cis-7,8-epoxy-2-methyloctadec-17-ene (= 7S,8R-epo-2me-17ene-18Hy) and unbaited traps. However, traps baited with 7R,8S-epo-2me-17ene-18Hy were less attractive than traps baited with (+)-disparlure [=(7R,8S)-cis-7,8-epoxy-2-methyloctadecane], the sex pheromone of L. dispar. Combination tests with (?)-disparlure, 7R,8S-epo-2me-17ene-18Hy, and 7S,8R-epo-2me- 17ene-18Hy revealed that 7R,8S-epo-2me-17ene-18Hy acted synergistically with (?)-disparlure.