Synthesis and Insecticidal Activity of New 2-Aryl-3,5-dihydro-2H-1,4-Benzoxazepine Derivatives

As part of a retrospective screening campaign from our legacy compounds collection to identify new chemical starting points for agrochemical lead discovery programs, we identified benzoxazepine compound I as a new insecticidal hit with potent foliar activity against sucking insects, such as aphids, whiteflies and scales. Aspects of the synthesis, structure-activity relationships, physico-chemical properties, and biology are described herein. Our lead optimization efforts led to the discovery of compound 2, which displayed improved potency and spectrum.