Journal of Chemical Ecology

, Volume 17, Issue 12, pp 2437–2447 | Cite as

Synthesis of the stereoisomers of the female sex pheromone of the Hessian fly,Mayetiola destructor

  • Jocelyn G. Millar
  • Stephen P. Foster
  • Marion O. Harris
Article

Abstract

The female-produced sex pheromone of the Hessian fly,Mayetiola destructor (Say) (Diptera: Cecidomyiidae), has been identified as (10E)-tridecen-2-yl acetate. A flexible synthetic route was developed which allowed access to the chiral and racemic forms of the pheromone, and to the 10Z stereoisomer of the pheromone. The natural compound was determined to have the 2S configuration by hydrolysis of the acetate function, derivatization of the resulting alcohol with (2S)-2-acetoxypropionyl chloride, and capillary gas Chromatographic comparison of the derivative with the corresponding derivatives prepared from the synthetic enantiomers. Trace amounts of the 10Z isomer of the pheromone have also been detected in extracts of female Hessian fly ovipositors, along with (10E)-tridecen-2-ol and 2-tridecanyl acetate. Due to the small quantities of these compounds available from ovipositor extracts, the chirality of the trace components has not yet been determined.

Key words

(10E)-tridecen-2-yl acetate (10Z)-tridecen-2-yl acetate sex pheromone Diptera Cecodomyiidae Hessian fly Mayetiola destructor 

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • Jocelyn G. Millar
    • 1
  • Stephen P. Foster
    • 2
  • Marion O. Harris
    • 3
  1. 1.Department of EntomologyUniversity of CaliforniaRiverside
  2. 2.D.S.I.R. Plant ProtectionPalmerston NorthNew Zealand
  3. 3.Department of EntomologyKansas State UniversityManhattan

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