Identification of a four-component sex pheromone blend in Bonagota cranaodes (Lepidoptera: Tortricidae)

Analysis of sex pheromone glands of the apple leafroller Bonagota cranaodes Meyrick by gas chromatography coupled with mass spectrometry or electroantennographic detection showed the presence of 14 structurally related acetates and alcohols of the chain length 10-18, including the main pheromone component (E,Z)-3,5-dodecadienyl acetate (E3,Z5-12Ac). Male antennae responded to the main compound, its Z,Z isomer, (E,Z) -3,5-tetradecadienyl acetate (E3,Z5-14Ac), and the monoenes (Z)-5-dodecenyl acetate (Z5-12Ac) and (Z)-9-hexadecenyl acetate (Z9-16Ac). Traps baited with a four-component blend of E3,Z5-12Ac, Z5-12Ac, E3,Z5-14Ac, and Z9-16Ac in a 100:5:5:100 ratio were significantly more attractive than the main compound alone. This improved trap lure is more suitable for monitoring population densities of B. cranaodes, and for detection of the onset of the seasonal flight period. A more complete pheromone blend is of importance also with respect to current attempts to develop mating disruption for control of this major pest of apple in Brazil.     

Antennal response of codling moth males, Cydia pomonella L. (Lepidoptera: Tortricidae), to the geometric isomers of codlemone and codlemone acetate

Single sensillum recordings from Cydia pomonella male antennae showed three different types of receptor neurons. The most abundant type was most sensitive to the main pheromone compound (E,E)-8,10-dodecadienol, while its response to the geometric isomers E,Z, Z,E and Z,Z was comparable to a tenfold lower dose of (E,E)-8,10-dodecadienol. This neuron type also responded to the four behaviorally antagonistic isomers of (Δ,Δ)-8,10-dodecadienyl acetate, among which it was most sensitive to the E,E isomer. Cross-adaptation studies showed that these compounds were all detected by the same receptor neuron type. Receptor neurons specifically tuned to (E,Z) or (Z,Z)-8,10-dodecadienol were not found, although these two compounds are behaviorally active. A second type of receptor neuron responded to all isomers of (Δ,Δ)-8,10-dodecadienyl acetate and was most sensitive to the E,E isomer. This neuron type did not respond to any of the isomers of (Δ,Δ)-8,10-dodecadienol. A third receptor neuron type was highly sensitive to the plant compound α-farnesene. The finding that the receptor neuron type tuned to the main pheromone compound responded even to strong behavioral antagonists aids the interpretation of ongoing behavioral studies for the development of the mating disruption technique in codling moth. Accepted: 3 March 2000     

Sex pheromone biosynthetic pathway in Spodoptera littoralis and its activation by a neurohormone

Deuterium-labeled fatty acids have been used to elucidate the sex pheromone biosynthetic pathway in Spodoptera littoralis. Label from palmitic acid was incorporated during the scotophase into all the pheromone acetates and their corresponding fatty acyl intermediates. (Z,E)-9,11-tetradecadienyl acetate, the major component of the pheromone blend, is synthesized from palmitic acid via tetradecanoic acid, which, by the action of a specific (E)-11 desaturase and subsequently a (Z)-9 desaturase, is converted into (Z,E)-9,11-tetradecadienoate. By further reduction and acetylation, this compound leads to the dienne acetate. Deuterated precursors applied to the pheromone gland during the photophase were also incorporated into the pheromone. The percentage of labeled (Z,E)-9,11-tetradecadienyl acetate relative to natural compound was significantly higher during the light period. Label incorporation from different intermediates into the pheromone was stimulated by injection of brain-subesophageal ganglion extract during the photophase. The influence of the pheromone biosynthesis-activating neuropeptide on the biosynthetic pathway is discussed.     

Sex pheromone of the African armyworm <Emphasis Type="Italic">Spodoptera exempta</Emphasis> (Lepidoptera: Noctuidae): identification of components of the Okinawan population and formulation for population monitoring

In 2010, abrupt outbreaks of the African armyworm, Spodoptera exempta (Walker), occured on the Tarama, Iriomote and Kikai Islands in southwestern Japan. Analysis by gas chromatography-electroantennographic detection (GC-EAD) revealed two EAG-active compounds on male antenna in crude extract of virgin females. These compounds were identified as (9Z)-9-tetradecenyl acetate (Z9-14:Ac) and (9Z,12E)-9,12-tetradecadienyl acetate (Z9E12-14:Ac) in ca. 90:10 ratio by subsequent GC-MS analyses. (11Z)-11-Hexadecenyl acetate (Z11-16:Ac), which had previously been identified as a third component in the Kenyan population, was not detected. Binary blends of Z9-14:Ac and Z9E12-14:Ac at ratios between 99:1 and 90:10 showed a potent attractiveness in the field, superior to that of virgin females and comparable to that of the three-component formulation determined in Kenya. For the population survey, a 98:2 blend was used. In Tarama, only a few moths of S. exempta were captured with a light trap during the night when more than 600 males were captured with synthetic sex pheromone; more S. exempta captures with a light trap had been reported than with sex-pheromone traps in Kenya. This indicates that the Okinawan population has different properties from the Kenyan population in pheromone composition and behavioral response to light.     

Chemical communication in heliothine moths. VII. Correlation between diminished responses to point-source plumes and single filaments similarly tainted with a behavioral antagonist

Addition of (Z)-11-hexadecenyl acetate (Z11-16:Ac) into a normally attractive binary blend of Heliothis virescens pheromone components resulted in a suppression of upwind flight and source location by males. Male response was reduced even at the lowest dosages of Z11-16:Ac tested but upwind flight and source location were most clearly reduced when the loading of Z11-16:Ac reached 10% or more of the (Z)-11-hexadecenal (Z11-16:Ald) loading (the major component present in the binary blend). Similar patterns of suppression in response were noted when Z11-16:Ac was added to binary blends of pheromone components at both 10 and 100 μg loadings of Z11-16:Ald. Males in casting flight following upwind flight in a mechanically generated pulsed plume, responded to the interception of a subsequent, single binary-blend filament by making a toward-source upwind surge. Responses of males to a single filament that was tainted by a level of Z11-16:Ac that had allowed some reduced level of upwind flight and source location to occur in the previous plume experiments were diminished compared with their control counterparts. Analysis of the flight tracks revealed that the surges in response to single tainted filaments were stunted because males made fewer significant changes in course angles steered, airspeeds generated, and in the tempo of counterturns executed. Accepted: 28 December 1996     

Sex pheromone of a North American population of the spotted tentiform leafminer, Phyllonorycter blancardella

The major sex pheromone compound of the spotted tentiform leafminer, Phyllonorycter blancardella (F.) (Lepidoptera: Gracillariidae), from Ontario, Canada, was identified as (10E)‐dodecen‐1‐yl acetate (E10‐12:Ac) using chemical analysis and field trapping experiments. The minor compounds (10E)‐dodecen‐1‐ol (E10‐12:OH) (4.6%), dodecan‐1‐ol (12:OH) (2.3%), and (10Z)‐dodecen‐1‐yl acetate (Z10‐12:Ac) 1.6% were also identified. The dienic acetate (4E,10E)‐dodecadien‐1‐yl acetate (E4,E10‐12:Ac), a compound reported to be attractive to P. blancardella, was not found in the glands of this population. A two‐component blend of the major and one of each the three minor compounds, in ratios similar to those found in the sex pheromone gland, did not increase the attractiveness of traps baited with synthetic pheromone. The minor compounds E10‐12:OH and 12:OH were not attractive to P. blancardella when tested individually. Z10‐12:Ac was attractive to P. blancardella, although traps baited with this compound captured only 2% of the moths that were captured in traps baited with the main compound. A four‐component blend of the major and each of the three minor compounds (100 : 1 : 1 : 1) was not more attractive than the major compound alone. The related species Phyllonorycter mespilella was captured in traps baited with E10‐12:Ac.     

Flight tunnel response of codling moth Cydia pomonella to blends of codlemone,codlemone antagonists and pear ester

Upwind orientation flights of codling moth males Cydia pomonella L. to a single source of sex pheromone (E,E)‐8,10‐dodecadienol (codlemone) are significantly reduced when blending it with pheromone antagonists, either with codlemone acetate, (E,E)‐8,10‐dodecadienyl acetate, or with the codlemone isomer (E,Z)‐8,10‐dodecadienol. However, once activated by a pheromone stimulus, males no longer distinguish between a pheromone source and these antagonistic blend sources. This shows that the pheromone stimulus required for the initiation of an upwind flight response differs from the stimulus for maintaining upwind flight and landing at the source. In contrast to pheromone antagonists, males discriminate between pheromone alone and a blend source of pheromone and the plant volatile pear ester, ethyl (2E,4Z)‐2,4‐decadienoate. This indicates a difference in the detection and neural integration of pheromone and plant volatile stimuli.     

Odour quality discrimination for behavioural antagonist compounds in three tortricid species

The antennal and behavioural response of three tortricid species (Lepidoptera: Tortricidae) to their corresponding sex pheromones and known or putative behavioural antagonists was tested by electroantennography and in field trials. The species and their pheromones and known or proposed behavioural antagonist were lightbrown apple moth, Epiphyas postvittana (Walker) [pheromone: 95% (E)‐11‐tetradecenyl acetate (E11‐14Ac) and 5% (E,E)‐9,11‐tetradecadienyl acetate (E9E11‐14Ac); antagonist: (Z)‐11‐tetradecenyl acetate (Z11‐14Ac)], codling moth, Cydia pomonella (L.) [pheromone: (E,E)‐8,10‐dodecadien‐1‐ol (codlemone); antagonist: (E,E)‐8,10‐dodecadienyl acetate (codlemone acetate)], and gorse pod moth, Cydia ulicetana (Haworth) [pheromone: (E,E)‐8,10‐dodecadienyl acetate (codlemone acetate); putative antagonist: (E,E)‐8,10‐dodecadien‐1‐ol (codlemone)]. In all three species, the antennal response to the antagonists was not significantly different from the antennal response to con‐specific sex pheromone compounds. In the field trapping experiments, significantly fewer males of all three species were attracted to the respective pheromone when blended with the behavioural antagonist compound. However, this response varied between the species, with lightbrown apple moth and codling moth showing stronger responses to the antagonist compounds than gorse pod moth. Both lightbrown apple moth and codling moth males were able to discriminate between pure pheromone and pheromone blended with the antagonist when placed in traps side‐by‐side separated by ca. 10 cm. The presence of the behavioural antagonist not only affected the catch of males of both species within their own traps but also affected the catch in the neighbouring trap that contained con‐specific sex pheromone; the catch of gorse pod moth was not reduced by the presence of codlemone in the neighbouring trap. These results suggest that strong behavioural antagonists such as codlemone acetate for codling moth and Z11‐14Ac for lightbrown apple moth induce their inhibition effect at a substantial distance downwind from the odour source; however, most of those males that were able to overcome this inhibition effect at the early stage of orientation to odour source, were able to discriminate between the pheromone source and the pheromone source admixed with behavioural antagonist. Moderate behavioural antagonists such as codlemone for gorse pod moth did not elicit a discrimination effect.     

Spatial discrimination of pheromones and behavioural antagonists by the tortricid moths Cydia pomonella and Adoxophyes orana

Male moths responding to their species-specific sex pheromone, may cease their upwind flight when pheromone components of sympatric species are added to the mixture. The interspecific interaction between the pheromone response of the tortricid moths Cydia pomonella and Adoxophyes orana was investigated in field-trapping and wind-tunnel studies. Addition of the A. orana pheromone [(Z9)-tetradecenylacetate and (Z11)-tetradecenylacetate] to a source containing the C. pomonella pheromone [(E8, E10)-dodecadienol] resulted in a significant inhibition of attraction by male C. pomonella. It is demonstrated that this behavioural antagonist for C. pomonella must be emitted from the same point source to induce this inhibitory effect. A spatial separation of the two interspecific pheromones (at 14 cm, 5 cm and 0.5 cm crosswind) restored the attraction of the conspecific pheromone for male C. pomonella. In contrast to C. pomonella, male A. orana were not inhibited by point sources releasing both the C. pomonella and A. orana pheromone. We suggest that the discrepancy in the interspecific pheromone interaction between these two tortricids can be explained if we consider the evolutionary ecology of interspecific pheromone communication in C. pomonella and A. orana. Accepted: 18 July 1999     

Number and sensitivity of three types of pheromone receptor cells inAntheraea pernyi andA. polyphemus

Summary Three types of receptor cells responding respectively to the pheromone components (E,Z)-6,11-hexadecadienyl acetate (AC₁, (E,Z)-6,11-hexadecadienal (AL) and (E,Z)-4,9-tetradecadienyl acetate (AC₂) occur in different combinations in the sensilla trichodea on male antennae ofAntheraea polyphemus andA. pernyi. The numbers of cells sensitive to AC₁ and AL and the average sensitivities of these cells are about equal, and higher than those of the AC₂-cells. The cells sensitive to AC₂ are relatively common in the small hairs positioned on the anterior side of the antenna. The product of three experimental values — (i) the relative number of each cell type, (ii) the average relative sensitivity of the cells and (iii) the estimated relative release rate of the respective pheromone component from the female gland — suggest that the distance from the female over which a compound can be detected or, the potential active space, is different for each pheromone component.Abbreviations EAG electroantennogram - SEM scanning electron microscope     

Notes on New Zealand mammals 10. Effect of observer position on group size and level of aggression of mating brown hares

Abstract

The sex pheromones of two endemic New Zealand tortricid species were investigated. Females of the first species, Cnephasia jactatana, a pest of kiwifruit, were found to produce (Z)-11-tetradecenyl acetate (Z11-14:OAc) in their sex pheromone gland. When tested in the field, this compound on its own elicited significant catches of male C. jactatana. However, the addition of even very small amounts (0.3%) of the geometric isomer, (E)-11-tetradecenyl acetate (E11-14:OAc), to Z 11-14:OAc virtually suppressed trap catches. The sex pheromone of the second species, Merophyas leucaniana, was found to consist of a mixture of Z11-14:OAc, E11-14:OAc, tetradecyl acetate, and (Z)-11-tetradecenol. This species is morphologically very similar to the congeneric species, M. divulsana, the Australian lucerne leafroller. The sex pheromone of M. leucaniana is also very similar to that of the so-called “Z-type” of M. divulsana, which is now found in New Zealand. The pheromone components of C. jactatana and M. leucaniana are discussed in relation to those found in other tortricids.     

Identification and field attraction of the female sex pheromone of a kiwifruit pest,Nokona feralis (Lepidoptera: Sesiidae)

Female sex pheromone of a clearwing moth Nokona feralis (Leech) (Lepidoptera: Sesiidae), a pest of kiwifruit, was identified to be a 7:3 mixture of (3E,13Z)-3,13-octadecadienyl acetate (E3,Z13-18:OAc) and (3E,13Z)-3,13-octadecadien-1-ol (E3,Z13-18:OH) by GC-EAD and GC/MS analyses. Males were attracted to wide-range mixtures of E3,Z13-18:OAc and E3,Z13-18:OH, and a 7:3 mixture of those two compounds strongly attracted the males in the field.     

Responses of Mamestra suasa male moths to synthetic pheromone compounds in a wind tunnel

The upwind flight and landing responses of male Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) to various synthetic chemicals were studied in a wind tunnel. A mixture of (Z)-11-hexadecenyl acetate (Z11-16: Ac) and (Z)-11-hexadecenal (Z11-16: Ald) elicited upwind flight responses past the midpoint of the wind tunnel, and both components were necessary for landing of the males to occur at the pheromone source point. The best response to the mixtures tested was to a ratio 100:1 (ng) of Z11-16: Ac and Z11-16: Ald (blend B).The addition of (Z)-9-tetradecenyl acetate (Z9-14: Ac) (10 ng) to blend B resulted in a significant decrease of upwind flight and landing responses. The inhibitory effect of this chemical when it is mixed with blend B, and the presence of a specific receptor for this compound in sensilla trichodea of male M. suasa, suggest that Z9-14: Ac is involved in the chemical communication between M. suasa and other sympatric species. The addition of (Z)-11-hexadecenol (Z11-16: OH) (1 or 10 ng) to blend B had no effect on male upwind flight and landing responses. This compound does not seem to be involved in the chemical communication of this species.

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Résumé L'observation et la comptabilisation des vols orientés et des atterrissages des mâles de Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) sur une source de phéromone de synthèse ont mis en évidence un mélange attractif appelé mélange B et constitué par 100 ng de Z11-16: Ac et 1 ng de Z11-16: Ald. L'attraction et l'atterrissage sont sous la dépendance du mélange de ces 2 composés. Les variations de leurs proportions relatives affectent les différentes phases du comportement de vol des mâles.L'addition de 10 ng d'acétoxy-1 tetradécène-9 Z (Z9-14: Ac) diminue significativement les proportions de vols orientés et d'atterrissages par rapport aux réponses obtenues avec le mélange B seul. L'effet inhibiteur de cette molécule sur l'attractivité du mélange B et la présence chez M. suasa d'un récepteur spécialisé dans la perception de ce composé suggèrent que le Z9-14: Ac est impliqué dans la communication chimique entre M. suasa et d'autres espèces sympatriques. L'addition d'hexadécènol-11 Z (Z11-16: OH) au mélange B à la dose de 1 ou 10 ng ne modifie pas les réponses des mâles. Ce composé ne semble pas impliqué dans la communication chimique chez M. suasa.

     

Fine-scale resolution of closely spaced pheromone and antagonist filaments by flying male Helicoverpa zea

The limits of a male moth's ability to resolve closely spaced odor filaments have been investigated. Male Helicoverpa zea normally respond to their conspecific sex pheromone blend by exhibiting an upwind flight, which culminates in source contact by at least 50% of the bioassayed individuals. When loaded onto the same filter paper source containing this hitherto attractive pheromone blend, or onto a separate filter paper and co-emitted from the same pipette source with pheromone, (Z)-11-hexadecenyl acetate severely reduced upwind flight and source contact by male H. zea. A similar level of upwind flight inhibition was recorded when the antagonist (Z)-11-hexadecenyl acetate was emitted from its own point source placed 1 mm upwind of the pheromone point source, both plumes being simultaneously emitted in a continuous mode to form a confluent strand. However, (Z)-11-hexadecenyl acetate was less effective in reducing upwind flight and source contact when it was isolated and pulsed from its own source, placed 1 mm either upwind, downwind or cross-wind of a pipette source from which pheromone was simultaneously being pulsed, such that both filaments were separated in time by 0.001–0. 003 s. These results suggest that male H. zea are able to distinguish between odor sources separated by as little as 1 mm in space and 0.001 s in time. Accepted: 31 March 1999     

Small plot mating disruption trials for tufted apple bud moth,Platynota idaeusalis, in Pennsylvania apple orchards

Mating disruption treatments for the tufted apple bud moth (TABM),Platynota idaeusalis (Walker), were tested in small plot trials in apple orchards in Pennsylvania. Treatments were evaluated by fruit injury and by capture of male TABM in traps baited with synthetic pheromone sources or virgin females. The TABM pheromone is a two component isomeric blend ofE-11-tetradecen-1-ol (E11-14:OH) andE-11-tetradecenyl acetate (E11-14:Ac). A 50∶50 ratio of these two components was used in standard monitoring septa and in mating disruption treatments released from either hollow fibers (‘fiber’) or PVC tubes (‘PVC’). Other pheromone blends tested included a 90∶10 ratio of E11-14: Ac and E11-14:OH (‘EAc’) and its reverse (‘EOH’), mixture ‘EAc’ with 30% of the Z-isomers (‘low AEc’), and a blend similar to the preceding with 2% Z9-12:Ac (‘generic’). These other blends were released from multi tube tape (‘tape’) or Shin-Etsu type rope (‘rope’) dispensers. Seasonal dispenser release rate in mg ha⁻¹ h⁻¹ was ca. 30 for the ‘rope’ dispensers, 14 for ‘PVC’ and 6 for ‘fiber’. ‘EAc-tape’ and ‘EOH-tape’ were equally effective in reducing catches of males in traps baited with synthetic lures and in traps baited with virgin females. Both treatments also reduced fruit injury. ‘EAc-rope’, ‘fiber’ and ‘PVC’ also were generally effective; whereas, the ‘low EAc’ and ‘generic’ treatments reduced trap capture less than 90% and did not reduce fruit injury. Dispenser density was positively correlated with reduction in trap capture for the ‘low EAc-rope’ and ‘genericrope’ treatments. Traps loaded with ‘fiber’ dispensers captured more male TABM than the other treatments in non-pheromone permeated environments. Trap capture of other tortricids was reduced in pheromone treatments. ‘EAc-rope’ and the ‘TABM’ treatments provided mean (s.e.) percent reduction in trap catch of 99.5 (0.4) and 42.9 (10.1), respectively, for the redbanded leafroller,Argyrotaenia velutinana (Walker), and 90.4 (6.8) and 90.4 (1.3), respectively, for the obliquebanded leafroller,Choristoneura rosaceana (Harris).     

植物气味化合物与斜纹夜蛾性信息素的协同作用

为提高现有性信息素对雄蛾的引诱活性, 本研究通过大量的田间试验探索植物气味化合物与斜纹夜蛾Spodoptera litura性信息素（顺9, 反11-十四碳二烯乙酸酯∶顺9, 反12-十四碳二烯乙酸酯=10∶1）的协同作用机制。从斜纹夜蛾寄主植物和花的气味化合物中, 选择9种有代表性的化合物, 并以一定剂量分别加入到斜纹夜蛾性信息素诱芯中, 在田间测试对雄蛾的引诱活性。结果表明: 在测试的9种植源性化合物中, 发现一定剂量(每个诱芯加入0.4 mg)的苯乙醛(PAA), 具有显著提高斜纹夜蛾性信息素的引诱作用, 而高剂量的苯乙醛则强烈抑制性信息素的引诱活性; 此外, 其他各种浓度的测试化合物或混合物对性信息素则没有统计上显著的增效作用。不同剂量的苯乙醛单个化合物及各种植物气味化合物组成的混合物对斜纹夜蛾也有微弱的引诱作用。苯乙醛必须要与性信息素的完整组分(以10∶1比例混合的顺9, 反11-十四碳二烯乙酸酯和顺9反, 12-十四碳二烯乙酸酯)混合才能起作用, 缺少顺9, 反12-十四碳二烯乙酸酯则没有引诱活性。本研究证明, 苯乙醛作为理想的性信息素诱芯增效剂, 可应用于建立更理想的斜纹夜蛾性信息素诱杀技术, 对性诱害虫防治和测报具有应用价值。     

Antagonistic Effect of (Z)-11-Hexadecen-1-ol on the Pheromone-Mediated Flight of Helicoverpa zea (Boddie) (Lepidoptera:Noctuidae)

Flight-tunnel experiments were conducted using Helicoverpa zea males to determine whether or not (Z)-11-hexadecen-1-ol (Z11-16:OH), a compound emitted by another heliothine moth species, Heliothis subflexa, is a behavioral antagonist when admixed with the two-component pheromone blend of H. zea. Males were less likely to fly upwind all the way to the source when 0.3% Z11-16:OH was present in the blend. Even 0.1% Z11-16:OH caused differences in the flight behavior of H. zea males; they steered more off the windline than males responding to the pheromone blend alone, resulting in more oblique track angles. Thus Z11-16:OH appears to act antagonistically, along with another compound, (Z)-11-hexadecen-1-ol acetate (Z11-16:Ac), when it is added to the H. zea pheromone blend.     

Sex pheromone components ofHeliothis maritima: chemical identification, flight tunnel and field tests

Three sex pheromonal components, (Z)-11-hexadecenal (Z11–16:Ald), (Z)-11-hexadecenol (Z11–16:OH), and hexadecanal (16:Ald), in a ratio of 88.0∶7.2∶4.8, were identified from ovipositor extracts of the fulvous clover moth,Heliothis maritima Grasl. (Lepidoptera: Noctuidae) by gas chromatographymass spectrometry. In addition, trace amounts of (Z)-9-hexadecenal (Z9–16:Ald) were detected in the extracts by GC. A blend of Z11–16:Ald, Z11–16:OH and 16:Ald in a ratio of 100∶6∶3, as well as in combination with 0.1 or 1 part Z9–16:Ald was tested at 0.01, 0.1, 1.0 and 10.0 μg doses in a flight tunnel. In flight tunnel tests male behavioral responses elicited by 0.1 or 1.0 μg doses of the 100∶6∶3∶1 blend were similar to those elicited by an ovipositor extract at 2 female equivalents. Deletion of Z9–16:Ald from the blend at 0.1 μg dose caused a decrease in the male response. In the field test, however, presence or absence of Z9–16:Ald did not significantly influence the number of males trapped in sticky traps with rubber septa containing 100 μg of the respective blends.     

Dienic analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum: Synthesis, conformational analysis and structure-activity relationships

Structure-activity relationships for (Z, E)-dienic analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied by electrophysiological single-cell recordings and molecular mechanics calculations. The biological activities of the dienic analogs are highly sensitive to the position of the additional (E) double bond. The experimental observations are well rationalized by the use of a receptor-interaction model in which the biological activity is determined by conformational energies required to mimic spatial relationships in the natural pheromone component. A biologically active conformation for this compound is suggested.     

Development of Sex Pheromone Trap for Monitoring Matsumuraeses falcana (Walshingham) (Lepidoptera: Tortricidae)

This study was carried out to find out an effective formulation for monitoring the soybean podborer, Matsumuraeses falcana (Walshingham), using its sex pheromone in Korea. A 1 : 1 : 1 mixture of (E)-8-dodecenyl acetate (E 8–12: Ac), (E,E)-8,10-dodecadienyl acetate (E 8 E 10–12: Ac) and (E,Z)-7,9-dodecadienyl acetate (E 7 Z 9–12: Ac) was an effective composition in monitoring M. falcana. A binary mixture of E 8–12: Ac and E 8 E 10–12: Ac was essential to attract M. falcana male moths. E 7 Z 9–12: Ac showed a synergistic effect on the attractiveness of 1 : 1 mixture of E 8–12: Ac and E 8 E 10–12: Ac. These chemicals alone showed little or no attractiveness to M. falcana. The sticky-typed wing trap baited with sex pheromone captured significantly more males than the water-pan trap. Trap catches within a soybean field were much more than those in perimeter trap. The trap-baited with sex pheromone gave a distinct fluctuation pattern of male catches throughout the flight seasons. Therefore, it can be expected that pheromone-baited trap provides a simple tool for monitoring the soybean podborer, M. falcana in Korea.