(2S,8Z)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, Rhopalomyia longicauda
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The sex pheromone of the chrysanthemum gall midge, Rhopalomyia longicauda (Diptera: Cecidomyiidae), the most important insect pest in commercial plantations of chrysanthemum, Dendranthema morifolium (Ramat.) Tzvel., in China, was identified, synthesized, and field-tested. Volatile chemicals from virgin females and males were collected on Porapak in China and sent to the United Kingdom for analysis. Coupled gas chromatographic–electroantennographic detection (GC-EAG) analysis of volatile collections from females revealed two compounds that elicited responses from antennae of males. These compounds were not present in collections from males. The major EAG-active compound was identified as 2-butyroxy-8-heptadecene by gas chromatographic (GC) retention indices, mass spectra, in both electron impact and chemical ionization modes, hydrogenation, epoxidation, and derivatization with dimethyldisulfide. The lesser EAG-active compound was identified as the corresponding alcohol. The ratio of butyrate to alcohol in the collections was 1:0.26. Racemic (Z)-8-heptadecen-2-ol and the corresponding butyrate ester were synthesized from (Z)-7-hexadecenyl acetate, and the synthetic compounds found to have identical GC retention indices and mass spectra to those of the natural, female-specific components. Analysis of the volatile collections on an enantioselective cyclodextrin GC column showed the natural pheromone contained (2S,8Z)-2-butyroxy-8-heptadecene. Field tests showed that rubber septa containing racemic (Z)-2-butyroxy-8-heptadecene were attractive to R. longicauda males. The (naturally occurring) S-enantiomer was equally as attractive as the racemate, while the R-enantiomer was not attractive to males, and did not inhibit the activity of the S-enantiomer. The attractiveness of the butyrate was significantly reduced by the presence of even small amounts of the corresponding alcohol.
KeywordsChrysanthemum gall midge Rhopalomyia longicauda Cecidomyiidae Sex pheromone (2S,8Z)-2-butyroxy-8-heptadecene (2S,8Z)-8-heptadecen-2-ol Field trapping
This work was funded by the National Science and Technology Support Projects in the 11th Five-year Plan of China (No. 2006BAD15B03, 2006BAD08A03 and 2006BAD02A16-4) and in part by the UK Horticultural Development Council and the Worshipful Company of Fruiterers. We thank Dr. K. M. Harris (former director of International Institute of Entomology, UK) and Prof. Junichi Yukawa (Entomological Laboratory, Faculty of Agriculture, Kyushu University, Japan) for identifying this insect species.
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