| 1. |
- Hansson, Bill S., et al.
(författare)
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Electrophysiological and chemical analysis of sex pheromone communication system of the mottled umber, Erannis defoliaria (Lepidoptera : Geometridae)
- 1990
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 16:6, s. 1887-1897
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Tidskriftsartikel (refereegranskat)abstract
- (Z,Z,Z)-3,6,9-nonadecatriene (Z3, Z6, Z9-19Hy) and (Z,Z)-3,9-cis-6,7-epoxy-nonadecadiene (Z3, Z9-cis-6,7-epo-19Hy) were identified in pheromone gland extracts from female Erannis defoliaria. The two components were found in a 1:3 ratio, with the main component, Z3, Z9-cis-6,7-epo-19Hy present at an amount of about 1.5 ng per female. The components were identified by means of gas chromatography-mass spectrometry, gas chromatography-electroantennography and gas chromatography-single sensillum recordings. Single sensillum measurements on the male antenna showed two physiological types of sensilla. One type was characterized by a large spike amplitude cell responding to Z3, Z9-cis-6,7-epoxy-19Hy and a small spike amplitude cell responding to Z3, Z6, Z9-19Hy. A second type responded only with a large spike amplitude cell to the epoxide, and this cell was inhibited by the triene. Of the two pheromone components, the epoxide gave the higher response in the EAG tests. Preliminary field tests support the identification of the pheromone components. The epoxide was also found to be present in the extract of the pheromone gland of Colotois pennaria, and males of C. pennaria and Agriopis marginaria were trapped by the mixture of the identified compounds.
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| 2. |
- Hansson, Bill S., et al.
(författare)
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Pheromone variation among eastern European and a western Asian population of the turnip moth Agrotis segetum
- 1990
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 16:5, s. 1611-1622
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Tidskriftsartikel (refereegranskat)abstract
- The female sex pheromone composition and the male electro-physiological response with respect to the three main sex pheromone components, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, were investigated in populations of Agrotis segetum from Armenia and Bulgaria. The percentage composition of the female-produced pheromone was 1:52:47 and 1:42:57 for the respective populations. Corresponding male receptor frequencies were 9:90:1 and 6:92:2. EAG response profiles of the male antennae were similar for the two populations. The populations from Armenia and Bulgaria differed from the earlier investigated French and Swedish populations, which have larger amounts of (Z)-5-decenyl acetate in gland extracts and have a majority of (Z)-5-decenyl acetate-sensitive receptors. Investigation of receptor frequencies on antennae of male Hungarian moths showed that individuals could be classified as either Swedish or Armenian/Bulgarian type. Males of the Swedish type were preferentially attracted to the three-component pheromone blend, whereas blends of (Z)-7-dodecenyl and (Z)-9-tetradecenyl acetate, and (Z)-7-dodecenol [pure or in mixture with (Z)-5-decenol] attracted the Armenian/Bulgarian type. The nature of pheromone variation among European and Asian populations of the turnip moth and possible mechanisms maintaining the variation are discussed.
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| 3. |
- Löfstedt, Christer, et al.
(författare)
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Pheromone differences between sibling taxa Diachrysia chrysitis (linnaeus, 1758) and D. tutti (Kostrowicki, 1961) (Lepidoptera Noctuidae)
- 1994
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 20:1, s. 91-109
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Tidskriftsartikel (refereegranskat)abstract
- The noctuid sibling taxa Diachrysia chrysitis s. str. and D. tutti, of yet uncertain taxonomic status, have previously been shown to possess differences in morphology and to be attracted to different mixtures of the two presumed pheromone components (Z)-5-decenyl acetate and (Z)-7-decenyl acetate. Typical D. tutti males (clearly broken forewing marking) are known to respond to a 2: 100 mixture of the two isomers, whereas D. chrysitis males (unbroken marking) are attracted to a 100: 10 mixture. We investigated female pheromone production and male electroantennographic (EAG) response in Diachrysia families raised in the laboratory from field-collected gravid females. Extracts of individual females from typical D. tutti and D. chrysitis families were subjected to gas chromatography with simultaneous flame ionization and electroantennographic detection. All females produced mixtures of Z5- and Z7-10:OAc, but female D. chrysitis produced predominantly Z5-10:OAc and the antennae of their brothers responded more strongly to the Z5 peak than to the Z7-10:OAc peak, whereas the opposite was true for D. tutti families. The pheromone components were shown to be biosynthesized from hexadecanoic and tetradecanoic acid, respectively by Z11-desaturation followed by chain shortening, reduction, and acetylation. The EAG responses of males trapped with the typical D. tutti and D. chrysitis blends, as well as with an intermediate blend, were investigated. Males trapped with the D. tutti mixture almost exclusively had a clearly broken wing marking and showed strongest EAG response to Z7-10:OAc. The intermediate blend and the D. chrysitis mixture gave more mixed catches, but with a prevalence of males with an unbroken (or almost unbroken) wing marking and with a higher mean response to Z5-10:OAc. Some males with typical D. tutti EAG responses were attracted in the field to the D. chrysitis pheromone. In the flight tunnel some D. chrysitis males were attracted also to the D. tutti mixture. This indicates that cross attraction may take place between the two taxa under natural conditions.
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| 4. |
- Tóth, Miklos, et al.
(författare)
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Attraction of male turnip moths Agrotis segetum (Lepidoptera : Noctuidae) to sex pheromone components and their mixtures at 11 sites in Europe, Asia, and Africa
- 1992
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 18:8, s. 1337-1347
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Tidskriftsartikel (refereegranskat)abstract
- Selected combinations of (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetates, the pheromone components of the turnip moth AgrotisSegetum were tested for field attractancy at six, two, and three sites in Europe, Asia, and Africa, respectively. At all of the sites in Eurasia and in northern Africa the ternary mixture of the acetates captured most males, while at the sites south of the Sahara in Africa, (Z)-5-decenyl acetate alone was responsible for attraction. Differences in male attraction among the populations studied confirm the existence of significant population variation in the pheromone of A. segetum. Interpretation of the present results together with earlier studies suggests that this variation is more or less continuous in Eurasia and north Africa, while a clearly distinct pheromone type is present in the areas south of the Sahara desert.
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| 5. |
- Tóth, Miklos, et al.
(författare)
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Epoxyheptadecadienes Identified as Sex Pheromone Components of Tephrina arenacearia Hbn. (Lepidoptera Geometridae)
- 1991
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Ingår i: Zeitschrift fur Naturforschung - Section C Journal of Biosciences. - : Walter de Gruyter GmbH. - 0939-5075. ; 46:3-4, s. 257-263
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Tidskriftsartikel (refereegranskat)abstract
- (Z, Z)-3, 9-cis-6, 7-Epoxyheptadecadiene, and (Z, Z)-6, 9-cis-3, 4-epoxyheptadecadiene were identified by gas chromatography/flame ionization detection-electroantennographic detection (GC/FID-EAD) and coupled gas chromatography-mass spectrometry (GC-MS) from abdominal tip extracts of Tephrina arenacearia (Lepidoptera: Geometridae), an alfalfa pest. In gas chromatography/flame ionization—single sensillum detection (GC/FID-SC) analyses, specific olfactory receptor cells were found for (Z, Z)-6, 9-cis-3, 4-epoxyheptadecadiene, and tricosane. Synthetic samples of racemic (Z, Z)-6, 9-cis-3, 4-epoxyheptadecadiene attracted large numbers of male T. arenacearia into traps. Best catches were observed at 100–1000 μg dosages. The addition of (Z, Z,Z)-3, 6,9-heptadecatriene did not influence catches. (Z, Z,Z)-3, 6,9-Heptadecatriene and (Z, Z)-6, 9-cis-3, 4-epoxyheptadecadiene were also identified in the pheromone gland extract of Chiasma clathrata, another geometrid pest of alfalfa.
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| 6. |
- Tóth, Miklos, et al.
(författare)
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Identification of four components from the female sex pheromone of the lima‐bean pod borer, Etiella zinckenella
- 1989
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 0013-8703. ; 51:2, s. 107-112
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Tidskriftsartikel (refereegranskat)abstract
- Four compounds, tetradecyl acetate, (Z)‐9‐tetradecenyl acetate, (E)‐11‐tetradecenyl acetate and (Z)‐11‐tetradecenyl acetate were identified from female sex pheromone extracts of Hungarian and Egyptian lima‐bean pod borers (Etiella zinckenella Tr., Lepidoptera: Phycitidae) by gas chromatography with flame ionization (FID) and electroantennographic (EAD) detection. In EAG studies these monounsaturated acetates gave the best responses in a series of other tetradecenyl acetates and tetradecenols. The four component blend of the identified components in similar ratios as in the pheromone extract attracted significant numbers of male lima‐bean pod borers in both Hungary and Egypt. In a preliminary subtraction test best capture was achieved by the ternary mixture of the monounsaturated acetates. Identification de quatre constituants de la phéromone des femelles d'Etiella zinckenella A partir de femelles d'E. zinckenella d'origines hongroise et égyptienne, nous avons isolé quatre composés par chromatographic en phase gazeuse avec ionisation de flamme et électroantennographie (EAD): l'acétate de tétradécanyl, l'acétate (Z)‐11‐tétradécényl, l'acétate (E)‐11‐tétradécényl et l'acétate (Z)‐11‐tétradécényl. Les acétates monoinsaturés donnent les meilleures réponses en EAG parmi une série d'acétates tétradécényls et de tétradécénols. Les quatre composés mélangés dans les mêmes proportions que dans l'extrait de la phéromone ont attiré un nombre significatif de mâles tant en Egypte qu'en Hongrie. Dans un test préliminaire de soustraction, la meilleure capture a été réalisée par le mélange ternaire d'acétates monoinsaturés. 1989 The Netherlands Entomological Society
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| 7. |
- Tóth, Miklos, et al.
(författare)
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Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)
- 1994
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Ingår i: Zeitschrift fur Naturforschung - Section C Journal of Biosciences. - : Walter de Gruyter GmbH. - 0939-5075. ; 49:7-8, s. 516-521
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Tidskriftsartikel (refereegranskat)abstract
- In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.
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| 8. |
- Tóth, Miklós, et al.
(författare)
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Sex pheromone components of Mamestra suasa : chemical analysis, electrophysiological activity, wind tunnel activity and field tests in two European countries
- 1986
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 0013-8703. ; 42:3, s. 291-299
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Tidskriftsartikel (refereegranskat)abstract
- (Z)‐11‐hexadecenyl acetate (Z‐11–16:Ac), (Z)‐11‐hexadecenal (Z‐11–16:Ald), (Z)‐11‐hexadecenol (Z‐11–16:OH) and hexadecanyl acetate (16:Ac) were found in pheromone gland extracts of female Mamestra suasa (Den. et Schiff.) in the relative amounts 100/2/10/5. All four compounds were also present in collections of airborne volatiles from calling females in a 100/7/5/5 ratio. No traces of 14 carbon aldehydes or acetates were detected. In gland extracts the presence of methyl hexadecanoate, methyl (Z)‐9‐hexadecenoate and methyl (Z)‐11‐hexadecenoate was demonstrated by base methanolysis. No methyl tetradecenoates were detected. In EAG tests Z‐11–16:Ac gave the best responses, followed by (Z)‐9‐tetradecenyl acetate (Z‐9–14:Ac), Z‐11–16:Ald and Z‐11–16:OH. In single sensillum recordings large spike amplitude cells in sensilla responded to Z‐11–16:Ac, while small spike amplitude cells to both Z‐11–16:OH and Z‐9–14:Ac. Cells responding to Z‐11–16:Ald were found in one out of 60 sensilla tested. In wind tunnel tests 0.1 μg of a 10:1 blend of Z‐11–16:Ac/Z‐11–16:Ald evoked the same responses and at a similar intensity as 3 isolated female pheromone glands did. In field tests a 10:1 blend of Z‐11–16:Ac/Z‐11–16:Ald caught significant numbers of males in both Bulgaria and Hungary. The addition of 16:Ac to the binary blend did not have any effect, while more than 1% of Z‐11–16:OH or 0.1170 of Z‐9–14:Ac dramatically decreased captures. In comparing different ratios of the acetate/aldehyde blend at different dose levels, best catches were recorded at the 10:1 ratio and at the highest (1000 μg) dose level. La composition de la phéromone sexuelle de Mamestra suasa***: analyse chimique, étude de l'effet par éléctrophysiologie et à la chambre de vol, et piégeages dans deux pays de l'Europe On a trouvé l'acetoxy‐1 hexadécene‐11 Z (Z‐11–16:Ac), le hexadécene‐11 Z al‐1 (Z‐11–16:Ald), le hexadécene‐11 Z ol‐1 (Z‐11–16:OH) et l'acetoxy‐1 hexadécene (16:Ac) dans des extraits de glandes phéromona les des femelles de Mamestra suasa. La proportion relative des composés était 100/2/10/5. Tous les quatre composés ont été présents aussi dans les collections d'émanations des femelles en stade d'appel, dans la proportion un peu différente de 100/7/5/5. On n'a détecté aucune trace des tétradécenes al‐1 ou d'acetoxy‐1 tétradécenes. On a démontré la présence de hexadécenoate‐1 methyl, hexadécene‐9 Z oate‐1 methyl et héxadécene‐11 Z oate‐1 methyl dans des extraits des glandes, par la méthode de ‘base methanolysis’. On n'a trouvé pas des tétradéceneoates methyl. En éléctroantennographie, Z‐11–16:Ac a donné les meilleurs réponses, suivis par l'acetoxy‐1 tétradécene‐9 Z (Z‐9–14:Ac), Z‐11–16:Ald et Z‐11–16:OH. Dans des études de ‘single sensillum’ les cellules à amplitude grande ont répondu à la stimulation avec de Z‐11–16:Ac, cependant les cellules à amplitude petite ont répondu à la stimulation avec des deux composés Z‐9–14:Ac et Z‐11–16:OH. On a trouvé des cellules sensitives à Z‐11–16:Ald dans 1 entre 60 sensilla étudiés. Á la chambre de vol, le dose de 0.1 μg d'un mélange de 10:1 de Z‐11–16:Ac/Z‐11–16:Ald a provoqué les mêmes réponses et à l'intensité pareille comme 3 glandes phéromonales isolées des femelles. En piégeages sur le champs des males en quantité importante ont été capturé par un mélange de 10:1 de Z‐11–16:Ac/Z‐11–16:Ald en Bulgarie et Hongrie. L'addition de 16:Ac au mélange binaire n'avait aucun effet, cependant l'addition de plus de 1% de Z‐11–16:OH ou 0.1% de Z‐9–14:Ac a sérieusement diminué les captûres. En comparant des proportions différentes du mélange de l'acetoxy/aldéhyde dans des doses différentes, on a observé les meilleurs captûres avec de la proportion 10:1 et à la dose la plus haute (1000 μg). 1986 The Netherlands Entomological Society
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| 9. |
- Wang, Hong-Lei, et al.
(författare)
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Biosynthesis and PBAN-regulated transport of pheromone polyenes in the Winter Moth, Operophtera brumata
- 2013
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 1573-1561 .- 0098-0331. ; 39:6, s. 790-796
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Tidskriftsartikel (refereegranskat)abstract
- The trienoic and tetraenoic polyenes, (3Z,6Z,9Z)-3,6,9-nonadecatriene, (3Z,6Z,9Z)-3,6,9-henicosatriene, and (3Z,6Z,9Z)-1,3,6,9-henicosatetraene were found in the abdominal cuticle and pheromone gland of the Winter Moth Operophtera brumata L. (Lepidoptera: Geometridae), in addition to the previously identified single component sex pheromone (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene. The pheromone biosynthesis activating neuropeptide (PBAN) is involved in the regulation of polyene transport from abdominal cuticle to the pheromone gland. In vivo deuterium labeling experiments showed that (11Z,14Z,17Z)-11,14,17-icosatrienoic acid, the malonate elongation product of linolenic acid, (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid, is used to produce (3Z,6Z,9Z)-3,6,9-nonadecatriene and (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene.
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