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Journal of Chemical Ecology

, Volume 19, Issue 10, pp 2129–2141 | Cite as

Enantiomeric composition of grandisol and grandisal produced byPissodes strobi andP. nemorensis and their electroantennogram response to pure enantiomers

  • B. E. Hibbard
  • F. X. Webster
Article

Abstract

Grandisol (cis-2-isopropenyl-1-methylcyclobutaneethanol) and its corresponding aldehyde, grandisal, were previously isolated and identified as aggregation pheromone components forPissodes strobi (Peck) andP. nemorensis Germar, but the enantiomeric ratios produced by these insects were not previously determined. We isolated grandisol and grandisal from males of bothP. strobi andP. nemorensis. The insect-produced grandisol was derivatized with trifluoroacetic anhydride, and the enantiomeric composition was determined by gas chromatography on an optically active cyclodextrin glass capillary column. The insect-produced grandisal was first reduced to grandisol before derivatization.P. nemorensis produced nearly 100% (1R,2S)-grandisol and nearly 100% (1S,2R)-grandisal.P. strobi produced 99% (1R,2S)-grandisol and approximately 60% (lR,2S)-grandisal. In electroantennogram (EAG) studies with liveP. nemorensis andP. strobi, no significant differences were found between the responses of males and females to racemic grandisol, racemic grandisal, or the 1R,2S and 1S,2R enantiomers of grandisol and grandisal, which is consistent with previous assertions that these compounds are aggregation pheromones. Although no studies to date withP. strobi have demonstrated a behavioral response to grandisol and grandisal,P. strobi antennae detected all enantiomers of grandisol and grandisal tested in EAG tests. The antennae of P.nemorensis responded significantly more to (1R,2S) grandisal than to (1S,2R)-grandisal, despite producing only (1S,2R)-grandisal.

Key Words

Pissodes strob Pissodes nemorensis grandisol grandisal 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • B. E. Hibbard
    • 1
  • F. X. Webster
    • 1
  1. 1.College of Environmental Science and ForestryState University of New YorkSyracuse

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