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Ethyl 4-[(6-substituted 2,2-dimethyl-2H-chromen-7-yl)methoxy]benzoates and their analogues were prepared and the biological activities were evaluated for both anti-juvenile hormone (anti-JH) and JH activity in silkworm larvae, Bombyx mori. Of the compounds tested, ethyl 4-[(6-methoxy-2,2-dimethyl-2H-chromen-7-yl)methoxy]benzoate (3b) showed the most effective precocious metamorphosis-inducing activity in 3rd instar larvae and JH activity in allatectomized 4th instar larvae. Furthermore, JH I and 20-hydroxyecdysone (20-E) titers in hemolymph of 3rd instar larvae treated with 3b were measured by liquid chromatography-mass spectrometry (LC-MS) and LC-MS/MS, respectively. The results revealed that compound 3b induced precocious metamorphosis by specifically decreasing JH I in hemolymph.

Synthesis and anti-juvenile hormone activity of ethyl 4-[(6-substituted 2,2-dimethyl-2H-chromen-7-yl)methoxy]benzoates