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Experientia

, Volume 51, Issue 4, pp 370–380 | Cite as

Sex pheromone of the pine sawflyDiprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity

  • G. Bergström
  • A. -B. Wassgren
  • O. Anderbrant
  • J. Fägerhag
  • H. Edlund
  • E. Hedenström
  • H. -E. Högberg
  • C. Geri
  • M. A. Auger
  • M. Varama
  • B. S. Hansson
  • J. Löfqvist
Research Articles

Abstract

The main component of the sex pheromone secretion of femaleDiprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as athreo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1–4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (>99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.

Key words

Diprion pini semiochemicals sex attractant 3,7-dimethyl-2-tridecanol chiral synthesis lipase chiral analysis 

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Copyright information

© Birkhäuser Verlag Basel 1995

Authors and Affiliations

  • G. Bergström
    • 1
  • A. -B. Wassgren
    • 1
  • O. Anderbrant
    • 2
  • J. Fägerhag
    • 3
  • H. Edlund
    • 3
  • E. Hedenström
    • 3
  • H. -E. Högberg
    • 3
  • C. Geri
    • 4
  • M. A. Auger
    • 4
  • M. Varama
    • 5
  • B. S. Hansson
    • 2
  • J. Löfqvist
    • 6
  1. 1.Chemical EcologyGöteborg UniversityGöteborgSweden
  2. 2.Department of EcologyLund UniversityLundSweden
  3. 3.Chemistry, Department of Science and Engineering Mid Sweden UniversitySundsvallSweden
  4. 4.Centre de Recherches d'OrleansInstitut National de la Recherche AgronomiqueOlivetFrance
  5. 5.Finnish Forest Research InstituteVantaaFinland
  6. 6.Department of Plant Protection SciencesSwedish University of Agricultural SciencesAlnarpSweden

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