Journal of Chemical Ecology

, Volume 32, Issue 12, pp 2667–2677 | Cite as

(2S,12Z)-2-Acetoxy-12-heptadecene: Major Sex Pheromone Component of Pistachio Twig Borer, Kermania pistaciella

  • Regine Gries
  • Grigori Khaskin
  • Hassan Daroogheh
  • Cafer Mart
  • Serpil Karadag
  • M. Kubilay Er
  • Robert Britton
  • Gerhard GriesEmail author


The sex pheromone of the pistachio twig borer, Kermania pistaciella (Lepidoptera: Oinophilidae), one of the most important insect pests of pistachio, Pistacia vera, in Turkey and Iran, was identified. In gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric analyses of pheromone gland extracts of female K. pistaciella from Turkey, (2S,12Z)-2-acetoxy-12-heptadecene was identified as the major candidate pheromone component. In field experiments in Turkey, lures containing synthetic (2S,12Z)-2-acetoxy-12-heptadecene attracted large numbers of male moths. Its attractiveness was significantly reduced by the presence of the R-enantiomer or of either enantiomer of the corresponding alcohol. (2S,12Z)-2-Acetoxy-12-heptadecene is the first pheromone component identified in the Oinophilidae and the first secondary acetate pheromone component identified in the Lepidoptera.


Pistachio twig borer Kermania pistaciella (2S,12Z)-12-Heptadecen-2-ol (2R,12Z)-12-Heptadecen-2-ol (2S,12Z)-2-Acetoxy-12-heptadecene (2R,12Z)-2-Acetoxy-12-heptadecene Sex pheromone Secondary acetate 



We thank Wittko Francke for lending us a custom-made chiral column and for review of the manuscript, Eberhard Kiehlmann and one anonymous reviewer for constructive comments, Micky Yang for elemental analyses, Sharon Oliver and Renée Picard for word processing, and Bob Birtch for graphical illustrations. The research was supported by a Discovery grant from the Natural Sciences and Engineering Research Council of Canada (NSERC) and by an NSERC-Industrial Research Chair to G.G. with Phero Tech Int., SC Johnson Canada, and Global Forest Science as industrial sponsors.


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Copyright information

© Springer Science+Business Media, LLC 2006

Authors and Affiliations

  • Regine Gries
    • 1
  • Grigori Khaskin
    • 1
  • Hassan Daroogheh
    • 2
  • Cafer Mart
    • 3
  • Serpil Karadag
    • 4
  • M. Kubilay Er
    • 3
  • Robert Britton
    • 5
  • Gerhard Gries
    • 1
    Email author
  1. 1.Department of Biological SciencesSimon Fraser UniversityBurnabyCanada
  2. 2.West VancouverCanada
  3. 3.Department of Crop Protection, Faculty of AgricultureKahramanmaras Sutcu Imam UniversityKahramanmarasTurkey
  4. 4.Pistachio Research InstituteGaziantepTurkey
  5. 5.Department of ChemistrySimon Fraser UniversityBurnabyCanada

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