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Isolement et identification de composés à activité phéromonale chez les femelles de l'arctiide Tyria jacobaeae: Détermination biologique de la configuration absolue du composé majoritaire (1988)

Frérot, B. ; Renou, M. ; Malosse, C. ; [et al.]

Springer

Entomologia experimentalis et applicata 46 (1988), S. 281-289

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ISSN: 1570-7458

Keywords: Lepidoptera ; Arctiidae ; Sex Pheronome ; Behaviour ; Electroantennography ; Physico-chemistry ; (Z,Z)-3,6-Cis-9S,10R-epoxyheneicosadiene ; (Z,Z)-3,6-Cis-9,10-epoxyeicosadiene ; (Z,Z,Z)-3,6,9-heneicosatriene ; Lépidoptère ; Arctiidae ; Phéromone sexuelle ; Comportement ; Electroantennographie ; Physicochimie ; Epoxy-9S,10R-(Cis) hénéicosadiène-3Z,6Z ; Epoxy-9,10-(Cis) éicosadiène-3Z,6Z ; Hénéicosatriène-3Z,6Z,9Z

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Description / Table of Contents: Abstract The hexanic extracts from pheronomal glands of T. jacobaeae virgin females have been studied. Gas-chromatographic and mass-spectrometric analyses of the main component (no 1) (98%) in combination with behavioral and electrophysiological bioassays allowed us to determine its structure and absolue configuration: (Z,Z)-3,6-Cis-(S,R)9,10-epoxyheneicosadiene previously described in other Arctiid moths. A minor constituent (no 2) (1.5%) was identified as (Z,Z)-3,6-Cis-(S,R)9,10-epoxyeicosadiene by comparison with synthetic compound. This structure is a new one for a lepidoptera sex pheromone. The third component (no 3) of the same extracts has the same physico-chemical data as those of a previously reported constituent of another Arctiid moth: (Z,Z,Z)-3,6,9 heneicosatriene.

Notes: Abstract Les analyses physico-chimiques d'extraits hexaniques de glandes à phéromone de femelles vierges de T. jacobaeae, associées à des études du comportement sexuel et à l'électroantennographie, ont permis d'identifier le composé majoritaire (98%) comme étant l'époxy-9S,10R-(Cis)-hénéicosadiène-3Z,6Z (no 1) et de déterminer sa configuration absolue. Les analogies entre les spectres du composé no 2 (1,5%) et ceux de l'époxy-9S,10R éicosadiène-3Z,6Z de synthèse nous conduisent à proposer cette structure pour ce constituant minoritaire. Le troisième produit (0,5%) possède les caractéristiques physico-chimiques de l'hénéicosatriène-3Z,6Z,9Z (no 3). Les produits 1 et 3 ont déjà été identifiés comme constituants de phéromones d'Arctiidae tandis que le produit 2 est décrit ici pour la première fois dans une sécrétion phéromonale de Lépidoptère.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00364200

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Sex pheromone of the european sunflower moth,Homoeosoma nebulellum (Den. & Schiff.) (Lepidoptera: Pyralidae) (1991)

Zagatti, P. ; Renou, M. ; Malosse, C. ; [et al.]

Springer

Journal of chemical ecology 17 (1991), S. 1399-1414

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ISSN: 1573-1561

Keywords: Lepidoptera ; Pyralidae ; Homoeosoma nebulellum ; European sunflower moth ; sex pheromone ; identification ; multicomponent blend ; (Z,E)-9,12-tetradecadienal

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Four components, (Z)-9-tetradecenal (8.6%), (Z,E)-9,12-tetradecadienal (4.8%), (Z)-11-hexadecenal (49.5%), and (Z)-13-octadecenal (37.1%), were identified in extracts of female pheromone glands of the European sunflower moth,Homoeosoma nebulellum (Lepidoptera: Pyralidae) using GC and GC-MS analyses. EAG and single-cell recordings of male antennal receptors gave strong evidence for (Z,E)-9,12-tetradecadienal as the antennal key compound of sex pheromone detection in this species. This result was confirmed by field trapping; removal of (Z,E)-9,12-tetradecadienal from quaternary blends completely suppressed the male catches. The synthetic blends with this compound as a major component caught five times less males than the blends reproducing the ratio found in the female extracts [5% of (Z,E)-9,12-tetradecadienal only]. The occurrence of a minor component perceived as the most biologically relevant compound is discussed.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00983772

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3

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Sex pheromone-mediated flight and landing behaviors of the European corn borer,Ostrinia nubilalis (Hübner) (1994)

Foster, S. P. ; Frérot, B.

Springer

Journal of chemical ecology 20 (1994), S. 2323-2343

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ISSN: 1573-1561

Keywords: Pheromone ; orientation ; visual cues ; plume structure ; Ostrinia nubilalis Lepidoptera ; Pyralidae

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract The pheromone-mediated flight and landing behaviors of maleOstrinia nubilalis were studied in a wind tunnel. The pheromone source was placed in the middle of an 18 × 18-cm horizontal surface, and a smaller surface placed 4, 18, or 36 cm downwind. The smaller surface did not appear to affect significantly the flight tracks or position of landing of males on the upwind surface, and it allowed the positions and altitudes of males as they passed over the downwind surface to be estimated. The flight altitude and position of males as they passed over the downwind surface related to where males landed on the upwind surface. Regardless of the downwind position of the downwind surface, most males flew over its center (i.e., in line with the source) and landed in line with the source on the upwind surface. When a small 2.5 × 10-cm vertical object was placed on the upwind surface, just upwind and to one side of the source, males flew over the downwind surface in positions skewed toward the vertical object and in broader distributions than for the comparable situation without an object: males landed on the upwind surface on positions skewed toward, or on, the object and with a broader distribution (laterally). Flight altitude also corresponded with landing position. Thus, when there was no vertical object, most males flew just above the downwind surface and landed on the downwind edge of the upwind surface. In contrast, with the vertical object, males flew significantly higher and tended to land past the downwind edge of the upwind surface. With a taller object (20 cm), males flew even higher, past the downwind edge and most landed on the vertical object. These data show the close relationship between flight and landing behaviors of maleO. nubilalis and suggest that flight maneuvers that determine track and altitude largely govern where a male lands.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF02033206

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Identification of hairpencil secretion from maleMamestra brassicae (L.) (Lepidoptera: Noctuidae) and electroantennogram studies (1991)

Jacquin, E. ; Nagnan, P. ; Frerot, B.

Springer

Journal of chemical ecology 17 (1991), S. 239-246

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ISSN: 1573-1561

Keywords: Mamestra brassicae ; Lepidoptera ; Noctuidae ; hairpencils ; male-produced compounds ; identification ; benzaldehyde ; 2-methylpropanoic acid ; 2-methylbutanoic acid ; benzyl alcohol ; 2-phenylethanol ; phenol ; electroantennography

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Extracts of maleMamestra brassicae (L.) hairpencils were analyzed by capillary gas chromatography (GC) and by GC-mass spectrometry (GC-MS). The extracts were found to consist of six components. Benzaldehyde, 2-methylpropanoic acid, 2-methylbutanoic acid, and phenol were present in the extracts as well as the previously identified benzyl alcohol and phenyl ethanol. The two major components were 2-phenylethanol and 2-methylbutanoic acid. They represented, respectively, 74% and 12.5% of the total blend in 3-day-old male extracts. Electroantennograms were recorded on male and female antennae in response to stimulation by hairpencil compounds. Male and female antennae responded to each chemical but the female responses were significantly higher than those of the males.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00994436

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5

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Sex pheromone evidence for two distinct taxa withinGraphania mutans (Walker) (1991)

Frérot, B. ; Foster, S. P.

Springer

Journal of chemical ecology 17 (1991), S. 2077-2093

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ISSN: 1573-1561

Keywords: Graphania mutans ; Lepidoptera ; Noctuidae ; sex pheromones ; (Z)-9-tetradecenyl acetate ; (Z)-9-tetradecenol ; (Z)-9-tetradecenal ; sibling species ; identification ; wind tunnel

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract The sex pheromones of two populations ofGraphania mutans (Walker) were analyzed. Females from an Auckland population produced (Z)-9-tetradecenol (Z9-14∶OH), (Z)-9-tetradecenyl acetate (Z9-14∶OAc), (Z)-7-tetradecenol (Z7-14∶OH) and (Z)-7-tetradecenyl acetate (Z7-14∶OAc), while females from a Lincoln population produced these four compounds and a large amount of (Z)-9-tetradecenal (Z9-14∶Ald). Significant differences, paralleling the difference between females, were observed when the responses of males of both populations to the above and other related compounds were tested by electroantennogram, field-trapping, and wind-tunnel bioassays. The most distinct difference was observed in the wind tunnel. Males from both taxa flew upwind and touched pheromone sources containing sex pheromone extract of females of their own taxon, but either did not initiate upwind flight or arrested upwind flight shortly after taking flight in response to extract from females of the other taxon. The difference between the pheromone systems of the two populations is probably due to the presence and importance of Z9-14∶Ald in the pheromone blend of the Lincoln population. Thus the addition of a relatively large amount of Z9-14∶Aid to a four-component pheromone blend (i.e., Z9-14∶OH, Z9-14∶OAc, Z7-14∶OH, andZ7-14∶OAc) attractive to Auckland males completely suppressed trap catches of male G.Mutans in Auckland but large numbers of males were caught at both Lincoln and Nelson in traps baited with this five-component blend. In wind-tunnel studies, the addition of even small (1% of amount of Z9-14∶OH) amounts ofZ9-14∶Ald to the four-component blend resulted in a significantly greater proportion of Auckland males arresting upwind flight than to the four-com ponent blend. It is suggested that these two populations of G. nations represent distinct sibling species within the described concept.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00987993

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6

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Sex pheromone ofPandemis heparana (Den. and Schiff.) (Lepidoptera:Tortricidae) (1982)

Frerot, B. ; Gallois, M. ; Lettere, M. ; [et al.]

Springer

Journal of chemical ecology 8 (1982), S. 663-670

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ISSN: 1573-1561

Keywords: Pandemis heparana ; sex pheromone ; Lepidoptera ; Tortricidae ; gas chromatography ; mass spectrometry ; insect behavior ; (Z)-11-tetradecen-1-yl acetate ; (Z)-9-tetradecen-1-yl acetate ; (Z)-11-tetradecenl-ol ; tetradecyl acetate ; dodecyl acetate

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract 90% (Z)-11-tetradecen-1-yl acetate, 5% (Z)-9-tetradecen-1-yl acetate, 5% (Z)-11-tetradecen-1-ol, dodecyl acetate (〈1%), and tetradecyl acetate (〈1%) were identified from gland extracts ofPandemis heparana females by gas chromatography and gas chromatography-mass spectrometry analysis (including mass fragmentography studies), chemical characterization, total synthesis, laboratory and field bioassays. In the field, a mixture of (Z)-11-tetradecen-l-yl acetate and (Z)-9-tetradecen-l-yl acetate (95∶5) was found to be essential for attractiveness ofP. heparana males.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00989635

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