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(Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae)

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Abstract

Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic–electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC–mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.

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Authors and Affiliations

  1. Centre for Pest Management, Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, Canada, V5A 1S6

    Gerhard Gries & Regine Gries

  2. Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada, V5A 1S6

    Keith N. Slessor, Grigori Khaskin, Priyantha D. C. Wimalaratne & Alan S. Tracey

  3. Canadian Forest Service, Pacific Forestry Centre, Natural Resources Canada, Victoria, British Columbia, Canada, V8Z 1M5

    Tom G. Gray & Mike Hulme

  4. Canadian Forest Service, Great Lakes Forestry Centre, Natural Resources Canada, Sault Ste. Marie, Ontario, Canada, P6A 5M7

    Gary G. Grant

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  1. Gerhard Gries
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  2. Keith N. Slessor
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Gries, G., Slessor, K.N., Gries, R. et al. (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae). J Chem Ecol 23, 19–34 (1997). https://doi.org/10.1023/B:JOEC.0000006343.38471.c7

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  • DOI: https://doi.org/10.1023/B:JOEC.0000006343.38471.c7

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