Sex pheromone of the moth,Antheraea polyphemus

The sex pheromone system of Antheraea polyphemus was characterized from female abdominal tips by classical and electroantennogram techniques as rans-6,cis-11-hexadecadienyl acetate and trans-6,cis-11-hexadecadienal. A 90 : 10 mixture of acetate and aldehyde was highly attractive to wild males in the field. The synthetic pheromone and A. polyphemus females were not attractive to released Antheraea pernyi males.     

Sex pheromone of the Asian corn borer moth

By 1975, insect sex pheromones had been identified from 60 species (1) of moths (Lepidoptera), and nearly all of the 40 compounds involved had been found to be mono- or di-unsaturated C₁₀ to C₁₈ straight-chain aldehydes, alcohols, or acetates, and the sites of olefinic unsaturation were, with one exception (2), at odd-numbered positions in the carbon chain. Since that time, many more lepidopteran pheromone components have been identified, and mono-unsaturated compounds with unsaturation at even-numbered positions in the carbon chain remain extremely rare (3–6). However, in females of $\text{Ostrinia furnacalis}$ (Guenee), called the Asian corn borer, we have discovered another mono-olefinic lepidopteran sex pheromone that has the site of unsaturation at ab even carbon position. Females of this corn-pest species produce a $\text{ca}$. 1:1 geometric mixture of ($\text{Z}$)- and ($\text{E}$)- 12-tetradecen-1-o1 acetate to attract and sexually stimulate males. On the other hand, the nearest taxonomic relative (7) of the Asian corn borer, the European corn borer, $\text{Ostrinia nubilalis}$ (Hübner), uses a mixture of ($\text{Z}$)- and ($\text{E}$)-11-tetradecen-1-o1 acetate as its sex pheromone (8). Biochemical explanation of the paucity of monounsaturated moth sex pheromones with olefinic sites at even numbered carbon positions remains to be elucidated.     

Sex pheromone of the iris gelechiid moth Monochroa divisella

The iris gelechiid moth, Monochroa divisella (Douglas) (Lepidoptera: Gelechiidae), is a serious pest in iris horticulture. The overuse of pesticides for conventional control has a great risk of water pollution because irises are often planted in damp areas. To minimize pesticide applications, it is essential to monitor moth emergence by using pheromone traps. The female pheromone of M. divisella was analyzed by means of gas chromatography‐electroantennographic detection (GC‐EAD) and GC‐mass spectrometry. Two male EAD‐active compounds were detected and identified as (Z)‐3‐dodecenyl acetate (Z3‐12:Ac) and (Z)‐5‐tetradecenyl acetate (Z5‐14:Ac), the amounts of which were ca. 40 and 6 ng per female (100:15), respectively. Synthetic Z3‐12:Ac alone attracted only a few males in field trap experiments, but the attractiveness was significantly enhanced when 15% (wt/wt) Z5‐14:Ac was added; traps baited with their binary mixtures captured 21.3‐106.4 males/trap/day, as compared with 2.3 males/trap/day attracted by a crude extract of 10 virgin females. We conclude that Z3‐12:Ac and Z5‐14:Ac are M. divisella pheromone components, which can be offered as an attractant in monitoring traps. Although dodecenyl acetates are a major class of lepidopteran pheromone components, those with the double bond at the 3 position are rare and appear to be unique to gelechiids.     

Sex pheromone of pear moth, Cydia pyrivora

The sex pheromone of the pear moth, Cydia pyrivora, is (E,E)-8,10-dodecadien-yl acetate. A 5%-addition of the geometric isomers E,Z and Z,Z decreased male attraction in the field, the Z,E isomer had no significant effect. Traps baited with 10 µg E,E on grey rubber septa were attractive throughout the flight period of C. pyrivora. These traps allow specific detection of pear moth, and they are not attractive to its sibling species, codling moth C. pomonella.     

Ontogeny of electroantennogram responses in the moth, Manduca sexta

The antennae of the moth, Manduca sexta, and the sensilla and sensory neurons they contain, develop during metamorphosis from pupa to adult. To determine when, during their development, antennae become capable of generating electrical responses to various stimuli, we recorded the electroantennogram (EAG), believed to be the summed extracellular record of receptor potentials, from developing and mature antennae. Antennae from male and female moths are similarly responsive to trans-2-hexenal, while only males respond to Manduca sex pheromone; these two odorants presumably stimulate separate receptors. Mechanical stimulation also elicits and EAG response. EAG responses to olfactory and mechanical stimuli are detectable several days before eclosion but not until the neurons are morphologically and biochemically quite mature. Responses increase in magnitude until the end of metamorphosis and then change little during the first 3 days after emergence of the adult. Responses to different stimuli do not develop synchronously.     

Sex pheromone components of the carpenterworm moth,Holcocerus vicarius

Extracts of the female sex pheromone gland of the carpenterworm moth, Holcocerus vicarius (Walker) (Lepidoptera: Cossidae), a pest of Ulmus pumila L. (Ulmaceae), were found to contain Z7‐tetradecenyl acetate (Z7‐14Ac), E3‐tetradecenyl acetate (E3‐14Ac), (Z3,E5)‐tetradecenyl acetate (Z3,E5‐14Ac), and Z7‐tetradecenyl alcohol (Z7‐14OH) by coupled gas chromatographic‐electroantennographic detection (GC‐EAD) and coupled gas chromatography‐mass spectrometry (GC‐MS). Field trapping studies with impregnated rubber septa indicated that Z7‐14Ac was essential for attraction of males of H. vicarius. However, the most attractive blend contained Z7‐14Ac, E3‐14Ac, Z3,E5‐14Ac, and Z7‐14OH in a 50:22:17:10 ratio. Our results demonstrated that a blend of Z7‐14Ac, E3‐14Ac, Z3,E5‐14Ac, and Z7‐14OH represented the sex pheromone of H. vicarius. The optimized four‐component lure blend may be useful for monitoring H. vicarius infestations and mating disruption.     

Sex pheromone production and perception in the mating disruption-resistant strain of the smaller tea leafroller moth, Adoxophyes honmai

Mating disruption is an environmentally safe plant protection strategy that uses a synthetic copy of an insect pheromone to interfere with sexual communication and hence reproduction. To date, a number of pest moths have been controlled with applications of formulated pheromones as mating disruptants. Recently, however, the first example of resistance to mating disruption was documented in one of the major tea pests in Japan, the smaller tea leafroller moth, Adoxophyes honmai Yasuda (Lepidoptera: Tortricidae). To avoid other such cases, it is important to elucidate the mechanism(s) by which the disruptant lost its effectiveness. To this end, we imposed further selection by rearing field‐collected resistant insects with a synthetic pheromone in the laboratory. After more than 70 generations of selection, a strain with quite strong resistance was established, males of which could find and copulate with their mates even in the presence of 1 mg l^?1 of disruptant. Although the mating ability of this strain was greatly increased, the composition and blend ratio of the sex pheromone produced and emitted by females were not obviously changed in comparison with those of females sensitive to mating disruption. However, male response to the pheromone blend was markedly broadened after selection so that resistant males could locate a synthetic pheromone source even when it lacked a pheromone component that is normally necessary for attraction. Males capable of locking onto off‐ratio pheromone blends may be better able to find calling females in pheromone‐treated environments than narrowly tuned males because of greater capability of overcoming sensory imbalance.     

Sex pheromone of the potato tuberworm moth, Phthorimaea operculella.

A compound was isolated from female $\text{Phthorimaea operculella}$ (Lepidoptera: Gelechiidae) abdominal tip extracts and identified as $\text{trans}$-4, $\text{cis}$-7-tridecadienyl acetate. The synthetic compound elicits male $\text{P. operculella}$ wing fanning and upwind orientation in the laboratory, and is attractive to males in the field. The corresponding alcohol also appeared to be present in the female extracts, but this compound was not found to increase male responses in the laboratory or the field. Another EAG active component was isolated but not identified.     

Sex pheromone components of the leafroller moth Pandemis cerasana

Female-tip washings of the leafroller moth, Pandemis cerasana, were found to contain (E)-11-tetradecenyl acetate, (Z)-11-tetradecenyl acetate, (E)-11-tetradecenol, (Z)-11-tetradecenol and tetradecyl acetate, based on chemical analysis and electroantennogram tests. The relative amounts of these compounds in the gland were ca. 64:21:10:3:2 in the order named. Only (E)-11 and (Z)-11-tetradecenyl acetate were required for attraction of males to trap dispensed in the ratio 3:1, respectively.     

Sex pheromone of the European pine shoot moth: chemical identification and field tests

The sex pheromone of the European pine shoot moth, Rhyacionia buoliana, has been isolated and, using chemical methods, its structure shown to be (E)-9-dodecenyl acetate. Field traps containing the synthetic pheromone were consistently more attractive than traps baited with unmated females.     

Sex pheromone precursors in the processionary moth Thaumetopoea pityocampa (Lepidoptera: Thaumetopoeae)

The fatty acid composition of Thaumetopoea pityocampa female sex pheromone gland was determined. In addition to the common C16 and C18 fatty acids, the glandular tissue contains large amounts of (Z)-11-hexadecenoate, (Z,Z)-11,13-hexadecadienoate, (Z)-13-hexadecen-11-ynoate and 11-hexadecynoate, as well as some unusual C18 fatty acids, such as (Z)-11 and (Z)-13-octadecenoic acids. From these results, different biosynthetic pathways are discussed for the formation of (Z)-13-hexadecen-11-ynyl acetate, the main component of the sex pheromone of the processionary moth.     

Sex pheromone biosynthesis in the processionary moth Thaumetopoea pityocampa by delta-13 desaturation

In vivo treatments of female sex pheromone glands of the processionary moth, Thaumetopoea pityocampa, with mass-labeled fatty acids showed that (Z)-13-hexadecen-11-ynyl acetate, the main sex pheromone component, is biosynthesized from palmitic acid by the combined action of delta-11 and delta-13 desaturases. The involvement of this unusual delta-13 has been proven by application of [16,16,16-2H3] [1,2-13C2]-hexadecanoic acid to the glands with a resultant incorporation of all labeled atoms into the pheromone and each one of the corresponding intermediates. These results seem to exclude alternative biosynthetic pathways, such as chain shortening and elongation combined with delta-11 desaturation. The delta-11 desaturase responsible for the formation of the triple bond in both the 11-hexadecynoyl and (Z)-13-hexadecen-11-ynoyl intermediates is also an unusual enzyme not previously reported in lepidopteran sex pheromone biosynthesis.     

中国印度谷螟性信息素次级组份的研究

印度谷螟是我国危害性较严重的仓储害虫之一,食性很广,几乎危害每一种植物性仓储物.印度谷螟雌虫性信息素主要成份顺9,反12-十四碳二烯醇醋酸酯(TDA)早已被鉴定,并利用TDA单一组份诱捕印度谷螟雄蛾也较为有效,但该虫的完整信息素系统尚不清楚.本研究采用单个雌蛾性信息素腺体抽提技术,利用毛细管气相色谱GC保留时间定性方法和气质联用GC-MS分析鉴定技术,从印度谷螟雌虫腺体提取物中鉴定了顺9,反12-十四碳二烯醇醋酸酯(A),顺9,反12-十四碳二烯醇(B),顺9,反12-十四碳二烯醛(C)和顺9-十四碳醋酸醋(D)4种主要信息素成份,其比例为A∶B∶C∶D=100∶22∶12∶9.风洞试验结果表明,以该4种主要成分按A∶B∶C∶D=8∶2∶1∶0.8比例配制成的诱芯,其引诱雄蛾的活性接近于雌蛾腺体提取物.     

Sex pheromone of the larch caterpillar moth, Dendrolimus superans, from northeastern China

A study was set up to determine the sources and rates of mortality of Bemisia tabaci (Gennadius) (Homoptera: Aleyrodidae) on field‐grown cassava in Uganda. Using a cohort‐based approach, daily direct observations were used to construct partial life tables for 12 generations of egg and nymph populations which were studied over a 1‐year period. Mortality was categorized as dislodgement, predation, parasitism (for nymphs only), unknown death, and inviability (for eggs only). The highest mean rate of marginal mortality across all stages was attributed to parasitism, with dislodgement and predation following, respectively. Across all factors, the highest mean rate of marginal mortality was observed in the fourth instar followed by the eggs, first‐, second‐, and third‐instars, respectively. Key factor analysis revealed that dislodgement was the major mortality factor contributing to generational mortality in eggs while for nymphs, parasitism in the fourth instar was the main driving force behind the observed generational mortality. Highest irreplaceable mortality in both the egg and nymph stages was attributed to dislodgement followed by parasitism and predation, and least was due to unknown death. Across stages, highest irreplaceable mortality rates were observed in the eggs and the fourth‐instar nymphs. The other stages had relatively low rates of irreplaceable mortality. Rain‐protection experiments revealed no significant differences in marginal mortality rates when compared to the open field situation.     

An inexpensive electronic device for measuring electroantennogram responses to sex pheromone components with a voltmeter

ABSTRACT. An inexpensive, portable device which allows measurement of electroantennogram (EAG) maximum amplitudes with a voltmeter instead of an oscilloscope is described. Potential advantages of the device include more rapid recording, low-cost construction of additional EAG recording systems for a laboratory with several users, and portability allowing studies in the field and occasional bench top use. The device is intended for use in conventional EAG recording, where EAG signals with rapid depolarizations are being measured, and where the maximum amplitude of the EAG signal is the only parameter of interest.     

Olfactory receptor responses to sex pheromone components in the redbanded leafroller moth

Electrical responses of single olfactory receptor neurons of the male redbanded leafroller moth were elicited by each of the principle components of the sex pheromone and six other behaviorally active compounds. Response frequencies to equal intensities of each of these compounds and changes in response frequency with increasing amounts of any one compound, varied from receptor to receptor. These differences in response characteristics appear to be due to factors intrinsic to the olfactory recptor neuron and not to factors external to it. The encoding of odor quality by these receptor neurons cannot be in the simple presence or absence of activity in any one of them. Rather, odor quality may be encoded by the pattern of activity which invariably arises across an ensemble of receptor neurons, each having its own distribution of sensitivities.     

Inhibitors of sensillar esterase reversibly block the responses of moth pheromone receptor cells

Three volatile alkyl-thio-trifluoro propanones inhibiting the esterase in olfactory sensilla of the silkmoths Antheraea polyphemus and A. pernyi were used to test the hypothesis that enzymatic pheromone degradation is responsible for the decline of the receptor potential after pheromone stimulation. Test stimuli were the pheromone components (E,Z)-6,11-hexadecadienyl acetate, a substrate for the sensillar esterase, and (E,Z)-6,11-hexadecadienal, not degraded by the esterase. Each compound acts on a separate type of receptor cell. In both receptor cell types the trifluoro propanones caused a partially reversible reduction of sensitivity as indicated by smaller receptor potential amplitudes and lower nerve impulse frequencies. Since application of the esterase inhibitors did not prolong the decline of the receptor potential of the acetate cell, the esterase is not responsible for the rapid pheromone deactivation. When the trifluoro propanones were applied after the pheromone at high concentrations, they rapidly inhibited (repolarized) both receptor cell types. Experiments with local application of trifluoro propanones revealed that the inhibitory effect spreads within seconds along the length of the sensillum. The inhibition of the electrophysiological responses might be due to an antagonistic action of the trifluoro propanones at the pheromone-binding sites, either at the receptor molecules or at the pheromone-binding protein. Accepted: 4 February 1998