Trogoderma inclusum

Me ester [25227-40-1 ]. Sex pheromone for the Khapra beetle Trogoderma inclusum. Also weak attractant for T. granarium. 

Sex pheromone of the Khapra beetle (Trogoderma inclusum) and T. granarium. 

The sex pheromone of Trogoderma inclusum is a mixture of the branched unsaturated ester (139) and its corresponding alcohol (138) and aldehyde (Scheme 26). Two syntheses giving raC mlC Material (113, 114) used the Wittig reaction to form the Z double bond. Optically active products were obtained by Mori (775) via the alkyl bromide-lithium alkyne coupling reaction followed by catalytic reduction. In a similar manner, Rossi and Carpita (776) prepared optically active S (138), its JS -isomer and the corresponding Z- and -aldehydes. 

Degraw, j. I., and J. O. Rodin Synthesis of methyl 14-methyl-cw-8-hexadecenoate and 14-methyl-cw-8-hexadecen-l-ol. Sex attractant of Trogoderma inclusum Le Conte. J. Org. Chem. 36,2902—2903 (1971). 

Four species of Trogoderma beetles use methyl-branched alkenals as their major sex pheromones 300). Aeration of T. gramrium and trapping of the volatiles on Porapak Q gave a 92 8 ratio of (Z)- to ( )-14-methyl-8-hexadecenal. The Z-isomer was the major component obtained from T. inclusum and T. variabile and the -isomer was obtained from T. glabrum. In laboratory bioassays males could discriminate between the geometric isomers. 

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