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Journal of Chemical Ecology

, Volume 18, Issue 1, pp 13–25 | Cite as

Abraxas grossulariata L. (Lepidoptera: Geometridae): Identification of (3Z,6Z,9Z)-3,6,9-heptadecatriene and (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene in the female sex pheromone

  • M. Tóth
  • H. R. Buser
  • P. M. Guerin
  • H. Arn
  • F. Schmidt
  • W. Francke
  • G. Szöcs
Article

Abstract

(3Z,6Z,9Z)-3,6,9-Heptadecatriene and (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene have been identified in female sex pheromone gland extracts ofAbraxas grossulariata L. (Lepidoptera: Geometridae). The compounds were detected by gas chromatography with electroantennographic detection (GC-EAD) and identified by GC-mass spectrometry (GC-MS). The amounts of hydrocarbon and epoxide were 0.13 and 0.42 ng/female, respectively. These identifications were confirmed by synthesis; the absolute configuration of the epoxide remains to be determined. Another isomeric epoxide, (3Z,6Z)-3,6-cis-9,10-epoxyheptadecadiene, was tentatively identified in small amounts (0.04 ng/female). Racemic (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene elicited the largest electroantennogram response within a series of heptadecadiene and nonadecadiene monoepoxides and the corresponding trienic hydrocarbons and, in field tests, attracted maleA. grossulariata into traps. Addition of 10% (3Z,6Z,9Z)-3,6,9-heptadecatriene to this epoxide enhanced attractiveness; addition of (3Z,6Z)-3,6-cis-9,10-epoxyheptadecadiene had no effect at low proportions while higher proportions caused a reduction in the numbers of males caught.

Key words

Pheromone identification (6Z,9Z)-6,9-cis-3,4-epoxyhepta-decadiene (3Z,6Z,9Z)-3,6,9-heptadecatriene Abraxas grossulariata Lepidoptera Geometridae 

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • M. Tóth
    • 1
  • H. R. Buser
    • 2
  • P. M. Guerin
    • 2
  • H. Arn
    • 2
  • F. Schmidt
    • 3
  • W. Francke
    • 3
  • G. Szöcs
    • 1
  1. 1.Plant Protection Institute of the Hungarian Academy of SciencesBudapestHungary
  2. 2.Swiss Federal Research StationWädenswilSwitzerland
  3. 3.Institute of Organic ChemistryUniversity of HamburgHamburg 13Germany

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