A number of ethyl 4-(2-benzylalkyloxy)benzoates were prepared and their activity to induce precocious metamorphosis was evaluated in larvae of the silkworm,
Bombyx mori, which was clearly recognized as a juvenile hormone (JH)-deficiency symptom. Ethyl 4-(2-benzylhexyloxy)benzoate (
6) and its 2-benzylheptyloxy analog (
7) were found to induce precocious metamorphosis at relatively low doses. Both enantiomers of
6 and
7 were prepared using a chiral auxiliary oxazolidinone. (
S)-Enatiomers were more active than (
R)-isomers at low doses of 0.1 and 1 μg, but at higher doses their activity was reversed. The activity of compound
6 could be fully counteracted by methoprene, a JH agonist, but not by the dietary administration of 20-hydroxyecdysone. The ester group was important in the ability to induce precocious metamorphosis. The (
S)-enatiomer of
6 prolonged the duration of the instar and delayed the onset of cocoon spinning when applied to 5th instar larvae, suggesting that this compound might have JH-like activity as well as anti-JH activity.
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