Abstract
A series of 1-(substituted phenoxyalkyl)imidazoles was prepared and evaluated for their activity to induce precocious metamorphosis in larvae of the silkworm, Bombyx mori, and to terminate diapause in pharate first-instar larvae of the wild silkmoth, Antheraea yamamai. Of the compounds tested, 1-[7-(4-ethylphenoxy)heptyl] imidazole (6) and its 4-methylphenoxy analog were the most active against B. mori larvae. Neither methoprene, a juvenile hormone mimic, nor tebufenozide, an ecdysteroid mimic, could fully counteract precocious metamorphosis induced by compound 6, but both hormone agonists were necessary for complete rescue. A variety of 1-(substituted phenoxyalkyl)imidazoles at 1 μg terminated diapause of A. yamamai at a percentage higher than 90%. 1-[5-(4-Ethylphenoxy)pentyl] imidazole (4) was the most effective. There was no apparent correlation between the ability of 1-substituted imidazoles to cause precocious metamorphosis in B. mori and diapause-terminating activity in A. yamamai.
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