有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1012-1015. 上一篇    下一篇

研究论文

新型N-(4,6-二取代嘧啶-2-基)-1-[取代吡啶(噻唑)甲基]-5-甲基-1H-1,2,3-三唑基-4-甲酰胺的合成与除草活性

严曼,石德清*,肖琳霞   

  1. (华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079)
  • 收稿日期:2007-08-29 修回日期:2007-11-26 发布日期:2008-06-26
  • 通讯作者: 石德清

Synthesis and Herbicidal Activity of Novel N-(4,6-Disubstituted pyrimidin-2-yl)-1-[substituted pyridyl(thiazolyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides

YAN Man, SHI De-Qing*, XIAO Lin-Xia   

  1. (Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemis-try,
    Central China Normal University, Wuhan 430079)
  • Received:2007-08-29 Revised:2007-11-26 Published:2008-06-26
  • Contact: SHI De-Qing

为了寻找新型低毒性的潜在除草剂, 以2-氯-5-(氯甲基)吡啶和2-氯-5-(氯甲基)噻唑为起始原料, 经过叠氮化, 然后与乙酰乙酸乙酯的环化, 水解, 卤化, 最后与2-氨基-4,6-二取代嘧啶的缩合反应, 合成了9种未见文献报道的目标化合物, 其结构经IR, 1H NMR, MS 和元素分析确证. 初步的生物活性测试结果表明, 所测目标化合物在100 mg/L浓度下显示出良好的除草活性.

关键词: 除草活性, 取代吡啶, 酰胺, 噻唑, 嘧啶, 1,2,3-三唑

In search of novel low toxicity and potent herbicides, nine title compounds were synthesized by the multi-step reaction using 2-chloro-5-(chloromethyl)pyridine or 2-chloro-5-(chloromethyl)thiazole as starting materials, followed by the cyclization with ethyl acetoacetate, hydrolysis, halogenation and the condensation with 2-amino-4,6-disubstituted-pyrimidines. The structures of the target compounds were characterized by IR, 1H NMR, MS spectra and elemental analysis. Preliminary bioassays show that the target compounds possess good herbicidal activities against selected weeds at a concerntration of 100 mg/L.

Key words: thiazole, amide, 1,2,3-triazole, pyrimidine, herbicidal activity, substituted pyridine