11,12-Methylenehexadec-l l-enoic acid and the amide were synthesized by the method of Baird et al. (1992) via a key intermediate, 1,2,2-tribromo-l-butylcyclopropane, which was debrominated and coupled with an alkylhalide resulting in a dialkylcyclopropene. Their activities as inhibitors of pheromone biosynthesis were examined with virgin females of the silkworm moth, Bombvx moyi, in vivo. Bombykol titer diminished in the pheromone glands treated with the cyclopropenes, and experiments utilizing [l-14C] or [16,16,16-2H3]hexadecanoic acids as a biosynthetic precursor showed that the cyclopropenes completely inhibited incorporation of the isotopes into bombykol and (Z)-11-hexadecen-l-ol at the dose of 1g per pheromone gland but accelerated incorporation into hexadecan-l-ol. These results revealed the acid and amide with a propene ring at the 11-position are inhibitors of desaturation step(s), Al 1-desaturation and possibly A 10,12-desaturation, in the biosynthetic pathway. The nitrile derivative with the propene ring did not inhibit the bombykol biosynthesis.
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