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Pheromonal Activity of Compounds Identified from Male Phyllotreta cruciferae: Field Tests of Racemic Mixtures, Pure Enantiomers, and Combinations with Allyl Isothiocyanate

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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.

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Acknowledgements

The study was partially supported by grant OTKA T 043289 of the Hungarian Academy of Science. The authors are indebted to K. Vig for consultations in the species determination of captured specimens and to M. Szatmáry and B. Strasser from the Research Institute for Medical Plants (Budakalász, Hungary) for providing their experimental fields for some tests.

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Tóth, M., Csonka, É., Bartelt, R.J. et al. Pheromonal Activity of Compounds Identified from Male Phyllotreta cruciferae: Field Tests of Racemic Mixtures, Pure Enantiomers, and Combinations with Allyl Isothiocyanate. J Chem Ecol 31, 2705–2720 (2005). https://doi.org/10.1007/s10886-005-7621-y

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