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A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae)

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Abstract

Analyses of the elytral hydrocarbons from male and female emerald ash borer, Agrilus planipennis Fairmaire, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9-methyl-pentacosane (9-Me-C25), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C25, which matched the natural compound by gas chromatography/mass spectrometry (retention time and EI mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular lipids. Hexane-washed females to which 9-Me-C25 had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex pheromone component of A. planipennis. This is the first contact sex pheromone identified in the Buprestidae.

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Acknowledgments

Funding was received from the Canadian Forest Service, the Ontario, New Brunswick, Saskatchewan, and Manitoba Departments of Natural Resources, and the US Forest Service, through SERG-International. We thank Hugh Evans, Jake St. Amour, Niall O'Brien, Ashton Kent, Gary Grant, and Gene Jones for assistance in the lab and field; Peter de Groot, Deepa Pureswaran, and Alex Mosseler for reviewing an earlier version of this manuscript and four anonymous reviewers; and we acknowledge the support of Ed Hurley, Ed Kettela, and Tony Hopkin. All experiments reported here comply with the laws of Canada.

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  1. Natural Resources Canada, Canadian Forest Service, Atlantic Forestry Centre, P. O. Box 4000, Fredericton, NB, E3B 5P7, Canada

    Peter J. Silk, Jon Sweeney & Junping Wu

  2. Natural Resources Canada, Canadian Forest Service, Great Lakes Forest Centre, 1219 Queen Street East, Sault Ste. Marie, ON, P6A 2E5, Canada

    Krista Ryall & D. Barry Lyons

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  1. Peter J. Silk
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  2. Krista Ryall
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Correspondence to Peter J. Silk.

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Silk, P.J., Ryall, K., Barry Lyons, D. et al. A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae). Naturwissenschaften 96, 601–608 (2009). https://doi.org/10.1007/s00114-009-0513-1

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