Pheromonal activity of compounds identified from male Phyllotreta cruciferae: Field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate

Miklós Tóth, Éva Csonka, Robert J. Bartelt, Allard A. Cossé, Bruce W. Zilkowski, Shin Etsu Muto, Kenji Mori

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Four himachalene sesquiterpenes and (+)-γ-cadinene, previously identified as possible pheromone components from males of a North American population of Phyllotreta cruciferae Goeze (Coleoptera, Chrysomelidae), were tested for attractiveness in field trapping experiments in Hungary. A mixture of the four synthetic racemic himachalene derivatives and (+)-γ-cadinene from a botanical source was slightly attractive to beetles, but much more attractive when blended with the known host-plant-derived attractant allyl isothiocyanate. This result was consistent with a previous study in North America. In tests with optically pure synthetic compounds, a blend of the same himachalene enantiomers found from male beetles was equivalent to the corresponding blend of racemic compounds, whereas a blend of the opposite enantiomers was not active. Through subtraction tests, it was found that the single compound, (6R,7S)-2,2,6,10-tetramethylbicyclo[5.4.0.]undeca-9,11-diene [compound (+)-A in this study], was as active as the whole mixture, suggesting that this compound is the key pheromone component of the European population of P. cruciferae. During field trials, several congeneric species, including P. vittula, P. nemorum, P. nodicornis, and P. ochripes, also were caught, suggesting that the same compound(s) may be relatively widespread as pheromone components in this genus.

Original languageEnglish
Pages (from-to)2705-2720
Number of pages16
JournalJournal of Chemical Ecology
Volume31
Issue number11
DOIs
Publication statusPublished - Nov 1 2005

Keywords

  • Cadinene
  • Chrysomelidae
  • Coleoptera
  • Electrophysiology
  • Enantiomer
  • Field trapping
  • Himachalene
  • Pheromone
  • Phyllotreta cruciferae
  • Phyllotreta spp.
  • Sesquiterpene

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

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