Novel Anthranilic Diamide Insecticides: Design, Synthesis, and Insecticidal Evaluation

• DOI: 10.1071/ch13701
• Publication Date: 2014-04-10T02:11:27Z
• Authors: Xuewen Hua; Wutao Mao; Zhijin Fan; Xiaotian Ji; Fengyun Li; Guangning Zong; Haibin Song; Juanjuan Li; Like Zhou; Lifeng Zhou; Xiaowen Liang; Genhao Wang; Xiaoyan Chen
• Keywords: Mythimna separata; Anthranilic acid; Pyrazole

Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed synthesized by coupling the active substructures diamides sulfoxaflor. The structures compounds confirmed infrared spectroscopy, 1H 13C NMR, elemental analysis. Several unique structural characteristics revealed via crystal structure analysis compound N-(2-(2-methyl-2-(methylthio)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 16e. Bioassay results indicated that most showed superior insecticidal activities against Mythimna separata Plutella xylostella when compared with positive control cyantraniliprole. In particular, N-(2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e excellent activity separata, a mortality rate 100 % at concentration 1 µg mL–1. These moieties, as important substructures, could improve or maintain promote novel pesticide development.