Thirty-two novel seven-membered azabridged compounds were constructed by starting material, succinaldehyde, and aniline hydrochlorides. Most of the compounds exhibited excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nilaparvata lugens). Various types of substitution were introduced into position 2, 3, and 4 of phenyl group. According to the bioassays, it was found that methyl group and fluorine atom on different sites of phenyl group was favorable to increase the insecticidal activities and position 2 was an important site for obtaining high-activity compounds. After further modifications, it was found that introducing disubstitution on position 2 and 5 of phenyl group could significantly increase the bioactivity against brown planthopper. Moreover, compared with IMI, the activity of compound 14 displayed 7 fold higher against armyworm and 20 fold higher against brown planthopper, while showing considerable activity against cowpea aphid. Compared with eight-membered azabridged neonicotinoids, seven-membered compounds showed excellent bioactivities against three species of pests, which implied that the framework of seven-membered azabridge could improve the insecticidal activities of neonicotinoid analogues and was a very good leading structure to discover potential pesticides.

Seven-membered azabrigded neonicotinoids constructed by succinaldehyde, aniline hydrochlorides, and nitromethylene analogs: Synthesis, crystal structure, and insecticidal evaluation

248th National Meeting (2014)

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