Tetrahydroindeno[1′,2′:4,5]pyrrolo[1,2-<i>a</i>]imidazol-5(1<i>H</i>)-ones as Novel Neonicotinoid Insecticides: Reaction Selectivity and Substituent Effects on the Activity Level

Abstract

Tetraheterocyclic tetrahydroindeno[1',2':4,5]pyrrolo[1,2-a]imidazol-5(1H)-one derivatives as novel neonicotinoid candidates were designed and prepared by selective etherification, chlorination and esterification of ninhydrin-heterocyclic ketene aminals adducts. Some of the designed compounds showed excellent insecticidal activity against cowpea aphids (Aphis craccivora), brown planthopper (Nilaparvata lugens), and armyworm (Mythimna separata). In particular, the activity against armyworm (Mythimna separata) improved a lot in contrast with that of imidacloprid and cycloxaprid. The research here provides a novel neonicotinoid chemotype for further development.