Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds.

(Z,Z)-6,9-Dienes with straight C18-C23 chains were synthesized from linoleic acid, and a C17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol. Oxidation of the homoconjugated dienes withm-chloroperoxybenzoic acid yielded a 1:1 mixture of two monoepoxides that could be separated by repeated medium-pressure liquid chromatography with a Lobar column. The chemical structure of each positional isomer was confirmed by analyses of the ozonolysis products, and the isomers showed characteristic(13)C signals in their NMR spectra and fragment ions in their EI mass spectra. In addition to the (Z,Z,Z)-3,6,9-trienes with straight C18-C23 chains and their monoepoxides, field tests using single source lures incorporating one of the above seven dienes and 14 monoepoxymonoenes were carried out in a forest in Tokyo from 1992 to 1994. Consequently, attraction of six geometrid species and five noctuid species was observed for the first time.