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

  • Gary J.R. Judd (a1), Regine Gries (a2), V. Marius Aurelian (a3) and Gerhard Gries (a2)

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.

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.

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Abd, Elkader S.Zaklama, S. 1971. The chemical control of the apple clearwing Synanthedon myopaeformis Bork. moth (Lepidoptera: Aegeriidae). Agricultural Research Review, 49: 7176.
Alford, D.V. 2007. Pests of fruit crops. Academic Press, Boston and San Diego.
Arn, H.Städler, E.Rauscher, S. 1975. The electroantennographic detector — a selective and sensitive tool in the gas chromatographic analysis of insect pheromones. Zeitschrift für Naturforschung, 30c: 722725.
Ateyyat, M.A.Al-Antary, T.M. 2006. Management and within-tree spatial distribution of the small red-belted clearwing borer, Synanthedon myopaeformis (Borkhausen) (Lepidoptera: Sesiidae), infesting dwarfing apple orchards in southern Jordan. Journal of the Entomological Society of British Columbia, 103: 1118.
Eichlin, T.D.Duckworth, W.D. 1988. The moths of America north of Mexico, including Greenland. Fascicle 5.1. Sesioidea, Sesiidae. The Wedge Entomological Research Foundation, Washington, D.C.
El-Sayed, A.M. 2009. The Pherobase: database of insect pheromones and semiochemicals [online]. Available from: [accessed 7 January 2011].
El-Sayed, A.M.Suckling, D.M.Wearing, C.H.Byers, J.A. 2006. Potential of mass trapping for long-term pest management and eradication of invasive species. Journal of Economic Entomology, 99: 15501564. doi:10.1603/0022-0493-99.5.1550
El-Sayed, A.M.Suckling, D.M.Byers, J.A.Jang, E.B.Wearing, C.H. 2009. Potential of “lure and kill” in long-term pest management and eradication of invasive species. Journal of Economic Entomology, 102: 815835. doi:10.1603/029.102.0301
Gries, R.Khaskin, G.Gries, G.Bennett, R.G.King, G.G.S.Morewood, et al. 2002. (Z,Z)-4,7-Tridecadien-(S)-2-yl acetate: sex pheromone of Douglas-fir cone gall midge, Contarinia oregonensis. Journal of Chemical Ecology, 28: 22832297. doi:10.1023/A:1021005517389
Judd, G.Philip, H. 2006. Apple clearwing moth, Synanthedon myopaeformis (Borkhausen): recent introduction to the Pacific Northwest pest complex. In Proceedings of 80th Annual Western Orchard Pest and Disease Management Conference, Portland, Oregon, 11–13 January 2006. p. 123 [Abstr.].
Judd, G.J.R.Gardiner, M.G.T.Thomson, D.R. 1997. Control of codling moth in organically-managed apple orchards by combining pheromone-mediated mating disruption, post-harvest fruit removal and tree banding. Entomologia Experimentalis et Applicata, 83: 137146. doi:10.1046/j.1570-7458.1997.00166.x
Leskey, T.C.Bergh, J.C. 2003. A simple character for sex differentiation of pupae and pupal exuviae of the dogwood borer (Lepidoptera: Sesiidae). Florida Entomologist, 86: 378380. doi:10.1653/0015-4040(2003)086[0378:ASCFSD]2.0.CO;2
Massee, A.M. 1954. The pests of fruits and hops. 3rd ed. Crosby Lockwood and Son Ltd., London, United Kingdom.
Shorey, H.H.Hale, R.L. 1965. Mass-rearing of the larvae of nine noctuid species on a simple artificial medium. Journal of Economic Entomology, 58: 522524.
Spatenka, K.Gorbunov, O.Lastuvka, Z.Tosevski, I.Arita, Y. 1999. Sesiidae — clearwing moths. Vol. 1. In Handbook of Palaearctic Macrolepidoptera. Edited by Naumann., C.M.. Gem Publishing Company, Brightwell, Wallingford, United Kingdom.
Systat Software Inc. 2003. SigmaStat. Version 3.0.1 [computer program]. Systat Software Inc., San José, California.
Szöcs, G.Tóth, M.Sziráki, G.Y.Schwarz, M. 1989. 2,13- and 3,13- octadecadienyl compounds composing sex attractants for tineid and sesiid moths (Lepidoptera). Biochemical Systematics and Ecology, 17: 417422. doi:10.1016/0305-1978(89)90059-8
Trematerra, P. 1993. On the possibility of mass-trapping Synanthedon myopaeformis Bkh. (Lep., Sesiidae). Journal of Applied Entomology, 115: 476483. doi:10.1111/j.1439-0418.1993.tb00417.x
Tumlinson, J.H.Yonce, C.E.Doolittle, R.E.Heath, R.R.Gentry, C.R.Mitchell, E.R. 1974. Sex pheromones and reproductive isolation of the lesser peachtree borer and the peachtree borer. Science (Washington, D.C.), 185: 614616. doi:10.1126/science.185.4151.614
Voerman, S.Minks, A.K.Van Wetswinker, G.Tumlinson, J.H. 1978. Activity of 3,13-octadecadien-1-ol acetates to the male clearwing moth Synanthedon myopaeformis (Borkhausen) (Lepidoptera, Sesiidae). Entomologia Experimentalis et Applicata, 23: 301304. doi:10.1111/j.1570-7458.1978.tb02749.x
Witzgall, P.Bengtsson, M.Rauscher, S.Liblikas, I.Bäckman, A.-C.Coracini, M. et al. 2001. Identification of further sex pheromone synergists in the codling moth, Cydia pomonella. Entomologia Experimentalis et Applicata, 101: 131141. doi:10.1046/j.1570-7458.2001.00898.x
Zar, J.H. 1984. Biostatistical analysis. 2nd ed. Prentice Hall, Englewood Cliffs, New Jersey.
Zhang, B.C. 1994. Index of economically important Lepidoptera. CAB International, Wallingford, United Kingdom.
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