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Journal of Chemical Ecology

, Volume 22, Issue 2, pp 357–368 | Cite as

Pheromone chirality of asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) (Coleoptera: Curculionidae)

  • Alice L. Perez
  • Rebecca H. Hallett
  • Regine Gries
  • Gerhard Gries
  • A. Cameron Oehlschlager
  • John H. Borden
Article

Abstract

Production of 4-methyl-5-nonanol, and 4-methyl-5-nonanone by two sympatric Asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) suggested that enantiospecificity of either compound could impart species specificity of pheromone communication. Weevil-produced, racemic 4-methyl-5-nonanol and 4-methyl-5-nonanone and their stereoselectively synthesized optical isomers were subjected to gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS) on a chiral Cyclodex-B column. Only theS,S stereoisomer of 4-methyl-5-nonanol was EAD active and was produced by bothR. ferrugineus andR. vulneratus. Production and EAD activity of (S)-4-methyl-5-nonanone exceeded that of its antipode in both weevils. In field experiments in Java. (4S, 5S)-4-methyl-5-nonanol and the stereoisomeric mixture were equally attractive. The 4R,5R stereoisomer was inactive. The corresponding ketone enantiomers neither enhanced nor reduced attraction to (4S,5S)-4-methyl-5-nonanol. Lack of apparent differences betweenR. ferrugineus andR. vulneratus pheromones suggests that synonomy of both weevils should be considered unless other pre- or postzygotic reproductive isolating mechanisms are disclosed in future studies.

Key Words

Coleoptera Curculionidae Rhynchophorus aggregation pheromone pheromone chirality 4-methyl-5-nonanol and 4-methyl-5-nonanone Asian palm weevils 

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Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • Alice L. Perez
    • 1
  • Rebecca H. Hallett
    • 2
  • Regine Gries
    • 2
  • Gerhard Gries
    • 2
  • A. Cameron Oehlschlager
    • 1
  • John H. Borden
    • 2
  1. 1.Department of ChemistrySimon Fraser UniversityBurnabyCanada
  2. 2.Centre for Pest Management Department of Biological SciencesSimon Fraser UniversityBurnabyCanada

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