Synthesis and anti-juvenile hormone activity of 1-substituted-5-((E)-2,6-dimethyl-1,5-heptadienyl)imidazoles.

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A new series of l-substituted-5-[(JE)-2,6-dimethyl-l,5-heptadienyl]imidazoles were prepared and bioassayed for anti-juvenile hormone activity on the silkworm, Bombyx mori.The compounds induced unequivocal precocious metamorphosis in the 3rd and 4th instar larvae by topical application.Of the compounds tested, l-benzyl-5-[(£)-2,6-dimethyl-l ,5-heptadienyl] imidazole (KK-42) proved to be the most active compound eliciting 100% of precocious pupation at 2/zg/larva on the 4th instar larvae.The E isomer showed considerably higher activity than the corresponding Z isomer.The anti-juvenile hormone effect of KK-42 was counteracted by simultaneous application of JH I or methoprene.