有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2131-2138.DOI: 10.6023/cjoc201701019 上一篇    下一篇

研究简报

含多氟烷基吡唑环的邻甲酰氨基苯甲酰胺类化合物的合成及杀虫活性

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 出版日期:2017-08-25 发布日期:2017-04-21
  • 通讯作者: 谭成侠 E-mail:tanchengxia@zjut.edu.cn
  • 基金资助:

    “十二五”国家科技支撑计划(No.2011BAE06B01-20)资助项目.

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 Online:2017-08-25 Published:2017-04-21
  • Contact: 10.6023/cjoc201701019 E-mail:tanchengxia@zjut.edu.cn
  • Supported by:

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

以2,3-二氯吡啶和水合肼为起始原料,经取代、缩合、氧化、醚化、成环和开环等多步反应合成一系列结构新颖的含多氟烷基吡唑环的邻甲酰氨基苯甲酰胺类化合物,结构经1H NMR和HRMS确证,并测试了目标化合物的杀虫活性.杀虫活性结果表明,在浓度0.8 mg/L下,大部分化合物对粘虫(Mythimna separata Walker)具有100%杀虫活性;在浓度2 mg/L下,N-(4-氯-2-(异丙基氨基甲酰)-6-甲基苯基)-1-(3-氯吡啶-2-基)-3-((1-甲基-3-五氟乙基-4-三氟甲基-1H-吡唑-5-基)氧基)-1H-吡唑-5-酰胺(8c)和N-(4-氯-2-(环丙基氨基甲酰)-6-甲基苯基)-1-(3-氯吡啶-2-基)-3-((1-甲基-3-五氟乙基-4-三氟甲基-1H-吡唑-5-基)氧基)-1H-吡唑-5-酰胺(8d)对斜纹夜蛾(Prodenia litura Fabricius)杀虫活性大于60%;在浓度0.08 mg/L下,N-(4-氯-2-(二甲基氨基甲酰)-6-甲基苯基)-1-(3-氯吡啶-2-基)-3-((1-甲基-3-五氟乙基-4-三氟甲基-1H-吡唑-5-基)氧基)-1H-吡唑-5-酰胺(8l)对小菜蛾(Plutella xylostella Linnaeus)杀虫活性达到82.5%.

关键词: 多氟烷基吡唑, 邻甲酰氨基苯甲酰胺, 合成, 杀虫活性

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