title: Tetrahydroindeno[1',2':4,5]pyrrolo[1,2-a]imidazol-5(1H)-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.
authors.affiliation: Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, and ‡Shanghai Collaborative Innovation Center for Biomanufacturing Technology, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
authors.forename: Nanyang
authors.initials: N
authors.lastname: Chen
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Meng
authors.forename: Fengjuan
authors.initials: F
authors.lastname: Zhu
authors.forename: Jiagao
authors.initials: J
authors.lastname: Cheng
authors.forename: Xusheng
authors.initials: X
authors.lastname: Shao
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D007093:Imidazoles / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D007093:Imidazoles; D007306:Insecticides; C029899:imidazole
keywords: activity; insecticide; synthesis; tetrahydroindeno[1′,2′:4,5]pyrrolo[1,2-a]imidazol-5(1H)-one