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Journal of Chemical Ecology

, Volume 28, Issue 11, pp 2283–2297 | Cite as

(Z,Z)-4,7-Tridecadien-(S)-2-yl Acetate: Sex Pheromone of Douglas-Fir Cone Gall Midge, Contarinia oregonensis

  • Regine Gries
  • Grigori Khaskin
  • Gerhard GriesEmail author
  • Robb G. Bennett
  • G. G. Skip King
  • Petra Morewood
  • Keith N. Slessor
  • W. Dean Morewood
Article

Abstract

Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 μg) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.

Douglas-fir cone gall midge Contarinia oregonensis Cecidomyiidae sex pheromone enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (Z,Z)-4,7-tridecadien-(R)-2-yl acetate 

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Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • Regine Gries
    • 1
  • Grigori Khaskin
    • 1
  • Gerhard Gries
    • 1
    Email author
  • Robb G. Bennett
    • 2
  • G. G. Skip King
    • 1
  • Petra Morewood
    • 1
  • Keith N. Slessor
    • 3
  • W. Dean Morewood
    • 1
  1. 1.Centre for Environmental Biology Department of Biological SciencesSimon Fraser University BurnabyCanada
  2. 2.Tree Improvement Branch SaanichtonMinistry of ForestsCanada
  3. 3.Department of ChemistrySimon Fraser University BurnabyCanada

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