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有机化学 ›› 2009, Vol. 29 ›› Issue (06): 929-935. 上一篇    下一篇

研究论文

N-桥连芳基吡咯类衍生物的合成、晶体结构及杀虫杀螨活性研究

毛春晖a,b; 赵 毓b; 李永强b; 黄润秋b; 毕富春b; 汪清民*,b   

  1. (a湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007)
    (b南开大学元素有机化学研究所 元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2008-10-07 修回日期:2008-11-30 发布日期:2009-06-20
  • 通讯作者: 汪清民

Synthesis, Crystal Structure, Insecticidal and Acaricidal Activities of Novel N-Bridged Derivatives of 2-(p-Chlorophenyl)pyrrole

Mao, Chunhuia,b; Zhao, Yub ; Li, Yongqiangb; Huang, Runqiub ;Bi, Fuchunb; Wang, Qingmin*,b
  

  1. (a National Engineering Research Center for Agrochemicals, Hunan Research Institute of
    Chemical Industry, Changsha 410007)
    (b State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic
    Chemistry, Nankai University, Tianjin 300071)
  • Received:2008-10-07 Revised:2008-11-30 Published:2009-06-20
  • Contact: Wang, Qingmin

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被引次数

16 | 3

以1-溴甲基-2-(4-氯苯基)-3-氰基-4-溴-5-三氟甲基吡咯为起始原料合成了3个新颖的N-桥连芳基吡咯类衍生物5a～5c. 通过氢谱、红外、元素分析及X射线单晶衍射确证了结构. 发现当2-(4-氯苯基)-3-氰基-4-溴-5-三氟甲基吡咯分别与S2Cl2, SCl2, 次磺酰氯, 亚磺酰氯反应时, 均未得到预期的N桥连产物, 却得到了Br被S取代的非预期产物. 杀虫杀螨活性结果显示目标产物5a～5c对东方粘虫、尖音库蚊幼虫、朱砂叶螨具有选择性, 如5a对东方粘虫具有很好的杀虫活性, 5a和5b在0.5 mg•g－1浓度下对尖音库蚊的杀虫活性为100%, 5b对朱砂叶螨具有很好的杀螨活性, 达到了商品化品种溴虫氰的水平.

关键词: 杀虫, N-桥连, 杀螨, 合成, 溴虫氰, 芳基吡咯

Three novel N-bridged derivatives of 2-(p-chlorophenyl)pyrrole were synthesized from 1-(bromomethyl)-2-(4-chlorophenyl)-4-bromo-5-(trifluoromethyl)pyrrole-3-carbonitrile, and characterized by 1H NMR, IR spectra, elemental analysis, and single crystal X-ray diffraction analysis. When 2-(4-chlorophenyl)-4-bromo-5-(trifluoromethyl)pyrrole-3-carbonitrile was treated with sulfur chloride, sul-fur dichloride, ethyl chlorothio(methyl)carbamate, and ethyl chlorosulfinyl(methyl)carbamate, respectively, only new structural Br-substituted products were obtained, without expected N-bridged products. The insec-ticidal activities of these new compounds 5a～5c against oriental armyworm and mosquito and acaricidal activities against spider mite were evaluated. The bioassays indicated that compound 5a exhibited excellent insecticidal activity against oriental armyworm, while those of compounds 5a and 5b and chlorfenapyr against mosquitos at 0.50 mg•kg－1 were 100%, and the acaricidal activity of compound 5b against spider mites was comparable to the commercialized chlorfenapyr.

Key words: chlor-fenap, insecticidal activity, N-bridged, acaricidal activity, synthesis, p-chlorophenylpyrrole