0023-6152

AA00697606

14056

Unrefereed

0023-6152

AA00697606

A series of alkyl 4-(2-benzylhexyloxy)benzoates and related compounds were synthesized and investigated for their ability to induce precocious metamorphosis in larvae of Bombyx mori, a clear sign of JH deficiency in the hemolymph of early larval stages. In the alkyl 4-(2-benzylhexyloxy)benzoate series, the methyl and ethyl (KF-13) esters induced precocious metamorphosis at relatively low doses. Replacement of the ester group with an amide, alcohol, oxime, ethyl or 3,4-methylenedioxy group eliminated the activity, indicating that the ester group on the benzene ring is essential for activity. A modification was made between the two benzene rings in KF-13. None of the compounds showed higher activity than KF-13 at low doses. The JH activity of synthesized compounds was assayed using allatectomized 4th instar larvae of B. mori. The aniline analog, which showed stronger precocious metamorphosis.inducing activity than KF-13 at higher doses, had obvious JH activity. The n.propyl ester possessing moderate precocious metamorphosis. inducing activity did not show any JH activity. There was some correlation between the ability of compounds to cause precocious metamorphosis and their JH activity.