Sabulodes caberata guenée (Lepidoptera: Geometridae) : Components of its sex pheromone gland

A 6,9-nonadecadiene, (Z)-9-nonadecene, andn-nonadecane were identified in extracts of sex pheromone glands of femaleSabulodes caberata Guenée. Potential pheromonal activity of gland components was assessed by electroantennogram measurements of gas-chromatographic fractions of abdominal tip extracts. Chemical identification was based on gas chromatography and mass spectrometry of parent compounds, hydrogenation products, ozonolysis products, dimethyl disulfide adducts, and synthesis. The monoene was synthesized via coupling of alkyl and acetylenic intermediates. (Z,Z)-6,9-Nonadecadiene (Z6,Z9-19∶H) was synthesized from methyl linoleate via chain lengthening. SyntheticZ6,Z9-19∶H had the same retention times on polar and nonpolar capillary gas-chromatographic columns as the 6,9-nonadecadiene from the sex pheromone glands. In field testsZ6,Z9-19:H alone produced trap catch of maleS. caberata and addition of (Z)-9-nonadecene orn-nonadecane had no effect on trap catch.