Identification of the Sex Pheromone of the Pink Grass Worm, Tmetolophota atristriga, Reveals Possible Population Differences in Male Response to Sex Pheromone (original) (raw)
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2022
The pink grass worm, Tmetolophota atristriga (Walker), is a New Zealand native species. It is abundant throughout the North and South Islands and is a pest which defoliates pasture. In this study, the sex pheromone of this species was investigated. Analysis of the extract of the female sex pheromone gland by GC/EAD, GC/MS and chemical derivatization identified six compounds: two monounsaturated compounds, (Z11)-hexadecenal (Z11-16:Ald) and (Z11)-hexadecenyl acetate (Z11-16:Ac), three saturated compounds, hexadecanal (16:Ald), hexadecyl acetate (16:Ac), octadecan-1-ol (18:OH), and a triene hydrocarbon, (3Z,6Z,9Z)-tricosatriene (Z3Z6Z9-23:Hy). Several field trapping experiments were conducted testing various pheromone blend combinations of the six identified compounds. Results suggested that the two different taxa of T. atristriga respond differently to the female sex pheromone compounds. The first taxon responds equally to the two-component and other blends including the six-componen...
Journal of Chemical Ecology, 2014
The sweet potato vine borer moth, Omphisa anastomosalis (Pyraloidea: Crambidae), is a serious pest in tropical and subtropical Asia-Pacific regions. In previous work using a population from Okinawa, Japan, (10E,14E)-10,14-hexadecadienal (E10,E14-16:Ald) was identified as the major pheromone component, with hexadecanal, (E)-10hexadecenal, and (E)-14-hexadecenal as minor components. However, traps baited with the synthetic compounds were less effective at attracting males in the field than those baited with virgin females. While Pyraloidea females usually produce only Type I pheromone components (unsaturated fatty alcohols and their derivatives), the pheromones of some Pyraloidea species have been shown to involve a combination of both Type I and Type II components (unsaturated hydrocarbons and their epoxides). We examined an extract of the pheromone glands of female O. anastomosalis from Vietnam by gas chromatography coupled to mass spectrometry and detected (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H) in addition to the compounds identified previously. All four isomers of 10,14-16:Ald were synthesized. A mixture of synthetic E10,E14-16:Ald and Z3,Z6,Z9-23:H in a ratio of 1:0.2-1:2 was attractive to male moths in Vietnam, indicating the strong synergistic effect of the Type II compound. Addition of the other minor pheromone components to the binary blend did not increase the number of male moths captured. Combinations of Z3,Z6,Z9-23:H with the other three geometrical isomers of E10,E14-16:Ald attracted no males, further substantiating the 10E,14E configuration of the natural diene component. E10,E14-16:Ald mixed with other polyunsaturated hydrocarbons showed that mixtures that included a C 21 triene, a C 22 triene, or a C 23 pentaene attracted as many males as did the mixture with Z3,Z6,Z9-23:H. The identification of a highly attractive sex pheromone will help in developing efficient strategies for monitoring and control of O. anastomosalis populations in sweet potato fields.
Bioscience, Biotechnology, and Biochemistry, 2006
Several geometrical isomers of 3,13-and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13-and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of ½M À 18 þ at m=z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)-and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.
Journal of Chemical Ecology, 2000
The sex pheromone blend of a European strain of the black cutworm moth, Agrotis ipsilon (Hufnagel), was investigated. Chemical analyses of pheromone gland extracts from 4-to 8-day-old females showed that individual isolated glands contained only very small amounts of pheromone. High-resolution gas chromatography combined with mass spectrometry (GC-MS) analyses showed the presence of c/s-T-dodecenyl acetate (Z7-12:Ac), cis-9tetradecenyl acetate (Z9-14:Ac), cis-11-tetradecenyI acetate (Zll-14:Ac), ci's-11-hexadecenyl acetate (Zl1-16: Ac), and cis-11-hexadecenol (Zll-16: OH) in biologically active pheromone gland extracts. Removing 27-12: Ac, Z9-14:Ac, or Zl1-16:Ac from the complete gland extract by GC trapping techniques strongly reduced the attractiveness of the pheromone blend tested in a wind tunnel. Lack of cis-5-decenyl acetate (Z5-10:Ac) or Zl1-16: OH did not affect the blend attractiveness. Chemical and behavioral analyses showed that pheromone components are produced during photophase, at least 2 hr before lights off. Quantitative data showed that decapitation inhibited the production of Z7-12:Ac, Z9-14:Ac, Zll-14:Ac, Zil-16:Ac, and Zll-16: OH, but production in decapitated females was stimulated in response to injection of synthetic Heliothis zea PBAN (pheromone biosynthesis activating
Sex Pheromone Components of Nettle Caterpillar, Setora nitens
Journal of Chemical Ecology, 2000
Gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts of female nettle caterpillars, Setora nitens, revealed four compounds that consistently elicited responses from male moth antennae. Retention indices on three fused silia columns (DB-5, DB-23, and DB-210) of two EAD-active compounds were almost identical to those of (E)-9-dodecenal (E9–12 : Ald) and (E)-9,11-dodecadienal (E9,11–12 : Ald), two pheromone components previously identified in congeneric Setothosea asigna. However, comparative GC, GC-EAD, and GC-mass spectrometry of extracted S. nitens compounds and authentic standards revealed that the candidate pheromone components were (Z)-9-dodecenal (Z9–12 : Ald) and (Z)-9,11-dodecadienal (Z9,11–12 : Ald). The two other EAD-active compounds in pheromone gland extracts proved to be the corresponding alcohols to these aldehydes. In field-trapping experiments in Tawau, Malaysia, synthetic Z9–12 : Ald and Z9,11–12 : Ald at a 1 : 1 ratio, but not singly, attracted male S. nitens. Attractiveness of these two aldehydes could not be enhanced through the addition of their corresponding alcohols. Whether these differences in pheromone biology and chemistry between S. nitens and S. asigna are sufficient to prevent cross-attraction of heterospecific males or whether nonpheromonal mechanisms are required to maintain reproductive isolation is currently being studied.
Naturwissenschaften, 2005
Using molecular-and sensory physiologybased approaches, three novel natural products, a simple ester, and a behavioral antagonist have been identified from the pheromone gland of the navel orangeworm, Amyelois transitella Walker (Lepidoptera: Pyralidae). In addition to the previously identified (Z,Z)-11,13-hexadecadienal, the pheromone blend is composed of (Z,Z,Z,Z,Z)-3,6,9,12,15-tricosapentaene, (Z,Z,Z,Z,Z)-3,6, 9,12,15-pentacosapentaene, ethyl palmitate, ethyl-(Z,Z)-11,13-hexadecadienoate, and (Z,Z)-11,13-hexadecadien-1-yl acetate. The C 23 and C 25 pentaenes are not only novel sex pheromones, but also new natural products. In field tests, catches of A. transitella males in traps baited with the full mixture of pheromones were as high as those in traps with virgin females, whereas control and traps baited only with the previously known constituent did not capture any moths at all. The navel orangeworm sex pheromone is also an attractant for the meal moth, Pyralis farinalis L. (Pyralidae), but (Z,Z)-11,13-hexadecadien-1yl acetate is a behavioral antagonist. The new pheromone blend may be highly effective in mating disruption and monitoring programs.
Journal of Chemical Ecology, 2013
The nettle moth Monema flavescens (Limacodidae) is a defoliator of fruit trees, such as Chinese plum and persimmon. The larvae of this species have spines containing a poison that causes serious irritation and inflammation in humans. Coupled gas chromatography-electroantennogram detection and gas chromatography/mass spectrometry analyses of a crude pheromone extract, combined with derivatization, indicated that female moths produced 8-decen-1-ol and 7,9-decadien-1-ol at a ratio of approximately 9:1. The E configuration of the double bonds was assigned for both components from infrared spectra, recorded on a gas chromatograph/Fourier transform-infrared spectrophotometer equipped with a zinc selenide disk cooled to −30°C. The monoenyl and dienyl alcohols had absorptions characteristic of E geometry at 966 and 951 cm −1 , respectively. A band chromatogram at 951 cm −1 was useful for distinguishing geometric isomers, because terminal conjugated diene are difficult to resolve, even on high polarity columns. Furthermore, we identified the Z configuration of the same 7,9-dienyl alcohol secreted by another nettle moth, Parasa lepida lepida, through the absence of this absorption. In field trials, lures baited with a 9:1 mixture of (E)-8-decen-1-ol and (E)-7,9-decadien-1-ol attracted M. flavescens males. Furthermore, the field trials indicated that contamination with the (Z)-diene reduced catches to the pheromone mixture more than did contamination with the (Z)-monoene.
Journal of Chemical Ecology, 1988
Ovipositor washings from virgin female Earias vittella (F.) (Lepidoptera: Noctuidae) moths were examined by gas chromatography (GC) linked to etectroantennography (EAG). Six components were detected by the male moth. These were identified by comparison of their retention times with those of a range of synthetic standards on fused silica capillary GC columns as hexadecanal, (Z)-ll-hexadecenal, (E,E)-10,12-hexadecadienal, octadecanal, (Z)-ll-octadecenal, and (E,E)-10,12-hexadecadien-1-ol in 1 : 2 : 10 : 2 : 4 : 1 ratio. Field testing in Pakistan showed that a 2 : 10 : 2 mixture of (Z)-11-hexadecenal, (E,E)-10,12-hexadecadienal, and (Z)-11-octadecenal was as attractive to male E. vittella moths as the six-component mixture and equal in attractiveness to a virgin female moth. Omitting (Z)-11-hexadecenal or (Z)-I 1-octadecenal greatly reduced this attractiveness. It was found that synthetic lures must be protected from sunlight to prevent loss of attractiveness caused by isomerization of the conjugated diene aldehyde, and addition of (E,Z)-10,12-hexadecadienal, one of the products of isomerization, was shown to reduce attractiveness significantly. During this work, a 10:1 mixture of (E,E)-10,12-hexadecadienal and (Z)-I 1-hexadecenal was shown to be as attractive to E. insulana (Boisd.) male moths as a virgin female moth, and the attractiveness of this mixture was further increased by addition of (E,Z)-10, l 2-hexadecadienal. 929 930 CORK ET AL.
Studies of the Female Sex Pheromone of the Native Budworm, Heliothis Punctiger
Entomologia Experimentalis et Applicata, 1982
Field screening tests indicated that males of the native budworm, Heliothis punctiger Wallengren (Lepidoptera: Noctuidae) were attracted to a 20:20:1 mixture of (Z)‐11‐hexadecenal (Z11‐16:ALD), (Z)‐11‐hexadecenyl acetate (Z11‐16:Ac) and (Z)‐9‐tetradecenal (Z9‐14:ALD), respectively. Inconsistent results were obtained when the Z11‐16:Ac in the blend was replaced by the corresponding alcohol, (Z)‐11‐hexadecenol (Z11‐16:OH). The presence of Z11‐16:ALD, Z11‐16:Ac and Z11‐16:OH in ovipositor washings from virgin females was confirmed by gas chromatographic (GC) and electroantennographic (EAG) analyses. Despite the field results, there was no evidence of Z9‐14:ALD in the virgin female extracts although this compound would not have been detected at levels below 0.5% of the total pheromone blend.RÉSUMÉÉtude de la phéromone sexuelle des femelles d‘Heliothis punctigerDes études de terrain sur l'attraction des mâles d'Heliothis punctiger (Wallengren) par des substances chimiques montren...