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3Z, 13Z-octadecadienyl acetate: sex pheromone of the apple clearwing moth in British Columbia

Published online by Cambridge University Press:  03 January 2012

Gary J.R. Judd ,
Regine Gries ,
V. Marius Aurelian  and
Gerhard Gries
Gary J.R. Judd*
Affiliation:
Pacific Agri-food Research Centre, Agriculture and Agri-food Canada, 4200 Highway 97, Summerland, British Columbia, Canada V0H 1Z0
Regine Gries
Affiliation:
Department of Biological Sciences, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6
V. Marius Aurelian
Affiliation:
Department of Biological Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2E9
Gerhard Gries
Affiliation:
Department of Biological Sciences, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6
*
1Corresponding author (e-mail: Gary.Judd@agr.gc.ca).
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Abstract

The apple clearwing moth, Synanthedon myopaeformis (Borkhausen) (Lepidoptera: Sesiidae), is a European species discovered in Cawston, British Columbia, Canada, in 2005. Using coupled gas chromatographic – electroantennographic detection analyses we identified candidate sex pheromone components in pheromone gland extracts and effluvia from calling females. Analysis of gland extracts using four gas-chromatography (GC) columns (DB-5, DB-17, DB-23, and DB-210) showed three components (A, B, and C) that consistently elicited strong responses from male antennae. Based on previous work, the most antennally stimulatory component, B, was hypothesized to be (3Z,13Z)-octadecadienyl acetate ((3Z,13Z)-18:OAc). Its retention time on the four GC columns and its mass spectrum in a concentrated extract matched those of an authentic standard, thus confirming structural assignment. Components A and C were below the detection threshold of the mass spectrometer, but their retention times on the four GC columns matched those of authentic standards of (3Z,13Z)-octadecadienol ((3Z,13Z)-18:OH) and (2E,13Z)-octadecadienyl acetate ((2E,13Z)-18:OAc), respectively. Synthetic (3Z,13Z)-18:OAc, (3Z,13Z)-18:OH, and (2E,13Z)-18:OAc all elicited strong responses from male antennae, further supporting structural assignments of these three components. Of these antennally active compounds, only (3Z,13Z)-18:OAc and (3Z,13Z)-18:OH were detected in effluvia from calling female moths. In field trapping tests in Cawston, (3Z,13Z)-18:OAc alone was as attractive as, or more attractive than, binary or ternary blends containing this component. (2E,13Z)-18:OAc was behaviourally inactive alone or in combination with (3Z,13Z)-18:OAc, whereas 5% (3Z,13Z)-18:OH appeared antagonistic. Our analysis confirms that (3Z,13Z)-18:OAc is the major pheromone component in S. myopaeformis, and it alone is sufficiently attractive for use in detection surveys and development of pheromone-based controls for this introduced pest in Canada.

Résumé

La sésie du pommier, Synanthedon myopaeformis (Borkhausen) (Lepidoptera : Sesiidae), est une espèce européenne retrouvée à Cawston, Colombie-Britannique, Canada, en 2005. À l'aide d'un couplage de chromatographie en phase gazeuse et de détection électroantennographique, nous avons identifié les composantes possibles de la phéromone sexuelle dans des extraits de glandes à phéromones et des émissions par des femelles en appel. L'analyse des extraits de glandes au moyen de quatre colonnes de chromatographie gazeuse (GC) (DB-5, DB-17, DB-23, et DB-210) révèle la présence de trois composantes (A, B, et C) qui provoquent toujours de fortes réactions dans les antennes des mâles. D'après des travaux antérieurs, nous pensons que la composante B, qui provoque la plus forte réaction dans les antennes, est l'acétate de (3Z,13Z)-octadécadiényle ((3Z,13Z)-18:OAc). Son temps de rétention sur les quatre colonnes de GC et son spectre de masse dans un extrait concentré correspondent à ceux d'un témoin authentique, ce qui confirme son assignation structurale. Les composantes A et C se situent sous le seuil de détection du spectromètre de masse, mais leurs temps de rétention sur les quatre colonnes GC correspondent à ceux de témoins authentiques respectivement de (3Z,13Z)-octadécadiénol ((3Z,13Z)-18:OH) et d'acétate de (2E,13Z)-octadécadiényle ((2E,13Z)-18:OAc). Les (3Z,13Z)-18:OAc, (3Z,13Z)-18:OH et (2E,13Z)-18:OAc synthétiques provoquent tous trois de fortes réactions dans les antennes mâles, ce qui appuie encore plus l'assignation structurale de ces trois composantes. De ces composantes stimulatrices des antennes, seuls le (3Z,13Z)-18:OAc et le (3Z,13Z)-18:OH se retrouvent dans les émissions des papillons femelles en appel. Dans des tests de piégeage à Crawston, le (3Z,13Z)-18:OAc seul produit autant, sinon plus d'attirance que des mélanges binaires ou ternaires contenant cette composante. Le (2E,13Z)-18:OAc, seul ou en combinaison avec le (3Z,13Z)-18:OAc, n'élicite aucun comportement, alors que le (3Z,13Z)-18:OH) à 5 % semble avoir un effet antagoniste. Notre analyse confirme que le (3Z,13Z)-18:OAc est la composante principale de la phéromone chez S. myopaeformis et qu'il produit par lui-même une attirance suffisamment forte pour être utilisé dans les inventaires de détection et la mise au point de témoins de phéromones pour ce ravageur introduit au Canada.

[Traduit par la Rédaction]

Type
Behavior & Ecology
Information
The Canadian Entomologist , Volume 143 , Issue 3 , June 2011 , pp. 236 - 244
Copyright
Copyright © Entomological Society of Canada 2011

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