| Title: | "(2S,8Z)-2-butyroxy-8-heptadecene: major component of the sex pheromone of chrysanthemum gall midge, Rhopalomyia longicauda" |
| Author(s): | Liu YJ; Hall D; Cross J; Farman D; Amarawardana L; Liu QR; He XK; |
| Address: | "Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, 100094, China" |
| DOI: | 10.1007/s10886-009-9647-z |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Linking) |
| Abstract: | "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" |
| Keywords: | "Animals Butyrates/*analysis/chemistry Diptera/*physiology Electrophysiology Female Gas Chromatography-Mass Spectrometry Male Sex Attractants/*chemistry Sexual Behavior, Animal Stereoisomerism;" |
| Notes: | "MedlineLiu, Ya-Jia Hall, David Cross, Jerry Farman, Dudley Amarawardana, Lakmali Liu, Qing-Ran He, Xiong-Kui eng Research Support, Non-U.S. Gov't 2009/06/26 J Chem Ecol. 2009 Jun; 35(6):715-23. doi: 10.1007/s10886-009-9647-z. Epub 2009 Jun 25" |
