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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

Xuewen Hua A B , Wutao Mao B C , Zhijin Fan A B E , Xiaotian Ji A B , Fengyun Li A B , Guangning Zong A B , Haibin Song A , Juanjuan Li A B , Like Zhou A B , Lifeng Zhou D , Xiaowen Liang D , Genhao Wang D and Xiaoyan Chen D
+ Author Affiliations
- Author Affiliations

A State Key Laboratory of Elemento-Organic Chemistry, Nankai University, No. 94, Weijin Road, Nankai District, Tianjin 300071, P. R. China.

B Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. China.

C College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Henan 473061, P. R. China.

D Jiangxi Tianren Ecological Co. Ltd, No. 181 Junshan Dadao, Jian, Jiangxi 343100, P. R. China.

E Corresponding author. Email: fanzj@nankai.edu.cn

Australian Journal of Chemistry 67(10) 1491-1503 https://doi.org/10.1071/CH13701
Submitted: 23 October 2013  Accepted: 22 February 2014   Published: 10 April 2014

Abstract

Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1H and 13C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of 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 of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the 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 showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100 % at a concentration of 1 µg mL–1. These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.


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