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(7Z,9E)-2-Methyl-7,9-Octadecadiene: A Sex Pheromone Component of Lymantria Bantaizana

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Abstract

Our objective was to identify the sex pheromone of Lymantria bantaizana (Lepidoptera: Lymantriidae) whose larvae feed exclusively on walnut, Juglans spp., in China, and Japan. Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed a single EAD-active component. Retention index calculations of this compound on four GC columns suggested that it was a methyl-branched octadecadiene with conjugated double bonds. In GC-EAD analyses of 2-methyloctadecenes, (Z)-2-methyl-7-octadecene and (E)-2-methyl-7-octadecene elicited the strongest antennal responses, suggesting that the double bond positions were at C7 and C9. In comparative GC-EAD analyses of pheromone gland extract and stereoselectively synthesized isomers (E,E; E,Z; Z,E; Z,Z) of 2-methyl-7,9-octadecadiene, the (E,Z)- and (Z,E)-isomer had retention times identical to that of the candidate pheromone, but only the latter isomer elicited strong EAD activity. Results of field experiments in Japan substantiated that (7Z,9E)-2-methyl-7,9-octadecadiene is the L. bantaizana sex pheromone, a compound previously unknown in the Lepidoptera. Detection surveys in North America for exotic Eurasian forest defoliators could include traps baited with the L. bantaizana pheromone.

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Acknowledgments

We thank Eberhard Kiehlmann for reviewing the manuscript. The research was supported, in part, by a contract from the State of California, Department of Food and Agriculture (contract #98-0508) and by grants from Global Forest (GF-18-2000-95; GF-18-2000-96) and the Natural Sciences and Engineering Research Council of Canada to G.G. Experimental insects were maintained in SFU’s Global Forest Quarantine Facility, the construction of which was completed through financial support from Global Forest (GF-18-2000-SFU-3).

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Authors and Affiliations

  1. Department of Biological Sciences, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6, Canada

    Regine Gries, Grigori Khaskin & Gerhard Gries

  2. Tohoku Research Center, Forestry and Forest Products Research Institute, 92-25 Nabeyashiki, Aza-Shimokuriyagawa, Morioka, Iwate, 020-0123, Japan

    Tadao Gotoh

  3. Agricultural Research Service, Beneficial Insects Introduction Research Laboratory, US Department of Agriculture, 501 S. Chapel Street, Newark, DE, 19713, USA

    Paul W. Schaefer

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  1. Regine Gries
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  2. Grigori Khaskin
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  4. Paul W. Schaefer
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  5. Gerhard Gries
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Correspondence to Gerhard Gries.

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Gries, R., Khaskin, G., Gotoh, T. et al. (7Z,9E)-2-Methyl-7,9-Octadecadiene: A Sex Pheromone Component of Lymantria Bantaizana. J Chem Ecol 31, 879–891 (2005). https://doi.org/10.1007/s10886-005-3550-z

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