INHIBITORY PHEROMONAL ACTIVITY PROMOTED BY SULFUR ANALOGS OF THE SEX-PHEROMONE OF THE FEMALE PROCESSIONARY MOTH THAUMETOPOEA-PITYOCAMPA (DENIS AND SCHIFF)

New sulfur analogs of the sex pheromone of the female processionary moth Thaumetopoea pityocampa have been found to be effective inhibitors of the natural pheromone activity both in EAG bioassays and field tests. The structures of these analogs have been derived from replacement of the oxygen atom(s) of the acetate group by sulfur (compounds 3-5) and the olefinic moiety of the enyne function by the isosteric SCH2 group (compounds 6 and 7). The synthesis and biological activity of 3-[(Z)-12-pentadecen-10-ynylthio]-1,1,1-trifluoropropan-2-one (8), a closely related structure to the pheromone is also described. © 1990 Plenum Publishing Corporation.