Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2131-2138.DOI: 10.6023/cjoc201701019 Previous Articles     Next Articles



史建俊a, 任贵华a, 吴宁捷b, 刘幸海a, 许天明b, 谭成侠a   

  1. a 浙江工业大学化学工程学院 杭州 310014;
    b 中化蓝天集团有限公司 浙江省化工研究院有限公司 杭州 310023
  • 收稿日期:2017-01-09 修回日期:2017-04-08 发布日期:2017-04-21
  • 通讯作者: 谭成侠
  • 基金资助:


Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety

Shi Jianjuna, Ren Guihuaa, Wu Ningjieb, Liu Xinghaia, Xu Tianmingb, Tan Chengxiaa   

  1. a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
    b Sinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd, Hangzhou 310023
  • Received:2017-01-09 Revised:2017-04-08 Published:2017-04-21
  • Contact: 10.6023/cjoc201701019
  • Supported by:

    Project supported by the National Key Technologies R&D Program of China during the 12th Five-Year Plan Period (No. 2011BAE06B01-20).

A series of novel anthranilic diamides containing polyfluoroalkyl pyrazole were synthesized using 2,3-dichloropyridine and hydrazine hydrate as starting materials via substitution, condensation, oxidation, etherification, cyclization and ring cleavage reaction. The title products were characterized by 1H NMR and HRMS. The bioassay results indicated that most of title compounds exhibited 100% insecticidal activitiy against Mythimna separata Walker at 0.8 mg/L, N-(4-chloro-2-(isopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8c) and N-(4-chloro-2-(cyclopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8d) showed more than 60% larvicidal activity against Prodenia litura Fabricius at 2 mg/L, and the mortality of N-(4-chloro-2-(dimethylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1Hpyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8l) against Plutella xylostella Linnaeus reached 82.5% at 0.08 mg/L.

Key words: polyfluoroalkyl pyrazole, anthranilic diamide, synthesis, insecticidal activity