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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 622-627. 上一篇    下一篇

研究论文

N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-1H-吡唑-5-基]菊酰胺类化合物的合成及生物活性

程敬丽，魏方林，朱烈，赵金浩，朱国念*   

  1. (浙江大学农业与生物技术学院农药与环境毒理研究所 杭州 310029)
  • 收稿日期:2007-04-25 修回日期:2007-09-30 发布日期:2008-04-17
  • 通讯作者: 朱国念

Synthesis and Biological Activities of N-[3-Cyano-1-(2,6-dichloro- 4-trifluoromethylphenyl)-1H-pyrazol-5-yl]-chrysanthemumamide

CHENG Jing-Li,WEI Fang-Lin,ZHU Lie,ZHAO Jin-Hao,ZHU Guo-Nian*   

  1. (College of Agriculture and Biotechnology, Zhejiang University, Hangzhou 310029)
  • Received:2007-04-25 Revised:2007-09-30 Published:2008-04-17
  • Contact: ZHU Guo-Nian

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为了寻求新的N-芳基吡唑类先导化合物, 用5种拟除虫菊酯类农药的活性基团——菊酸与高活性杀虫剂氟虫腈和其中间体5-氨基-3-氰基-1-(2,6-二氯-4-三氟甲基-苯基)吡唑在其氨基位置采用亚结构对接的方法合成得到了10个新的芳基吡唑菊酰胺类化合物. 经1H NMR, ESI-MS和元素分析对化合物的结构进行了表征. 初步生物活性测定结果表明, 在37.5 mg/L浓度下, N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-4-(三氟甲基亚磺酰基)-1H-吡咯-5-基]-3-(2,2-二氯乙烯基)-2,2-二甲基环丙酰胺(3b)对小菜蛾Amaranthus spinosus抑制活性达到100%, LC50为15.1 mg/L. 初步雌雄大鼠急性经口毒性综合评价属中毒级, 同时还检测了2-(4-氯苯基)-N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-1H-吡唑-5-基]-3-甲基丁酰胺(3i)的晶体结构.

关键词: N-芳基吡唑, 杀虫活性, 晶体结构, 毒性

In order to find new semicarbazide lead compounds, ten N-[1-(2,6-dicholoro-4-trifluoromethyl- phenyl)-1H-pyrazol-5-yl]-chrysanthemumamides were synthesized from five types of chrysanthemic acids with fipronil or 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazol-3-carbonitrile. The structures of all new compounds were confirmed by 1H NMR, MS spectra and elemental analysis. At the concentration of 37.5 mg/L, compound 3b shows inhibitory activity (100%) against Plutella xylostella Linnaeus. The LC50 of this compound is 15.1 mg/L. The oral acute toxicity of this compound to big male and female rats is middle. The crystal structure of 3i is also presented. The results indicate that it is rational and feasible to find new active compounds based on the connection between the active compound and the pharmacophore.

Key words: insecticidal activity, N-arylpyrazole, single crystal, toxicity