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Identification, Synthesis and Field Testing of (3Z,6Z,9Z)-3,6,9-Henicosatriene, a Second Bioactive Component of the Sex Pheromone of the Autumn Gum Moth, Mnesampela privata

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Abstract

The sex pheromone of Mnesampela privata, an endemic pest of Eucalyptus plantations in Australia, was previously identified as a single bioactive compound, (3Z,6Z,9Z)-3,6,9-nonadecatriene (C19 triene). Initial field testing of lures containing 1 mg, 5 mg or 10 mg of C19 triene (>98% purity) caught no or very few male M. privata. (3Z,6Z,9Z)-3,6,9-Henicosatriene (C21 triene) was identified as an additional minor pheromone component in abdominal tip extracts of M. privata females from Tasmania. Levels of both compounds extracted from individual females varied greatly, but the ratio was relatively constant at 33:1 C19:C21 trienes. Electroantennograms (EAG) of synthetic C21 triene with male M. privata gave positive but consistently lower responses than elicited by the C19 triene. Field tests showed that the addition of 1–6% C21 triene to 1 mg C19 triene significantly increased trap catch and the detection of M. privata in plantations. Traps baited with a 16:1 ratio caught significantly more moths than those baited with a ratio approximating that of females.

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Acknowledgements

This research was funded by the Australian Research Council Linkage Projects grant LP0455303. We thank Gunns Ltd, Forestry Tasmania, Timbercorp, WAPRES, and FFIC for funding and assistance. PPM is thankful to the University of Tasmania and the Thomas Crawford Foundation for a postgraduate scholarship. Thanks also to: Dr. Peter McQuillan (University of Tasmania) and Dr. Cathy Young (Tasmanian Museum and Art Gallery) for identifying geometrids, Dr. Mamoru Matsuki (IPMG, Albany) for conducting trapping trials in Western Australia and supplying moths for analysis, Mr. Ben Bradshaw (Timbercorp, Penola) for conducting trapping trials in Victoria and South Australia, and Dr. Martin Steinbauer for help with comments on the manuscript and the formulation of the original grant. We are also grateful for the financial support (for AN, FA, and EH) from the European Regional Development Fund and Länsstyrelsen i Västernorrlands län.

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Correspondence to Paul W. Walker.

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Walker, P.W., Allen, G.R., Davies, N.W. et al. Identification, Synthesis and Field Testing of (3Z,6Z,9Z)-3,6,9-Henicosatriene, a Second Bioactive Component of the Sex Pheromone of the Autumn Gum Moth, Mnesampela privata . J Chem Ecol 35, 1411–1422 (2009). https://doi.org/10.1007/s10886-009-9717-2

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  • DOI: https://doi.org/10.1007/s10886-009-9717-2

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