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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (08): 1287-1293. 上一篇    下一篇

研究简报

4,5-二氢-1,3,4-噻二唑-5-酮-2-甲氨基取代氰基丙烯酸酯类化合物的 合成及生物活性研究

王婷婷; 邴贵方; 张 欣; 秦振芳; 于海波; 秦 雪;
戴 红; 方建新*
  

  1. (南开大学元素有机化学国家重点实验室 天津市农药科学重点实验室 天津 300071)
  • 收稿日期:2009-03-20 修回日期:2009-05-12 发布日期:2009-08-30
  • 通讯作者: 方建新

Synthesis and Bioactivities of 2-Cyanoacrylates Containing 4,5-Dihydro-5-oxo-1,3,4-thiadiazol-2-yl Moiety

Wang, Tingting ; Bing, Guifang ; Zhang, Xin; Qin, Zhenfang; Yu, Haibo ;
Qin, Xue ; Dai, Hong; Fang, Jianxin*
  

  1. (State Key Laboratory of Elemento-organic Chemistry & Tianjin Key Laboratory of Pesticide Science,
    Nankai University, Tianjin 300071)
  • Received:2009-03-20 Revised:2009-05-12 Published:2009-08-30
  • Contact: Fang, Jianxin

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2061

被引次数

21 | 8

采用氰基丙烯酸酯与5-甲氧基-1,3,4-噻二唑-2-甲氨在乙醇中加热回流的方法合成了一系列4,5-二氢-1,3,4-噻二唑-5-酮-2-甲氨基取代的氰基丙烯酸酯类化合物. 目标化合物结构均经1H NMR, IR和元素分析确证. 生物活性测试结果表明: 部分化合物对双子叶杂草显示出较好的除草活性及良好的选择性, 化合物6j在1.5 kg/ha的剂量下对油菜的茎叶处理抑制率达到100%; 部分化合物还表现出了一定的杀菌和植物生长调节活性. 构效关系研究发现氰基丙烯酸酯3-位取代基的体积对除草活性影响较大, 3-位为异丙基时活性最高.

关键词: 4,5-二氢-1,3,4-噻二唑-5-酮, 氰基丙烯酸酯, 除草活性

A series of novel 2-cyanoacrylates containing a 4,5-dihydro-5-oxo-1,3,4-thiadiazol-2-yl moiety were synthesized from (5-methoxy-1,3,4-thiadiazol-2-yl)methanamine and 2-cyanoacrylates in refluxing ethanol. Their structures were confirmed by 1H NMR, IR spectra and elemental analysis. Biological activity tests showed that some compounds exhibited good herbicidal activities and good selectivity against dicoty-ledonous weeds. Compound 6j showed the highest herbicidal activity at the dose of 1.5 kg/ha with 100% in-hibition activity against rape. Some of the target compounds also possessed good fungicidal activity and plant growth regulatory activity. An appropriate size group at the 3-position of acrylate is essential for high herbicidal activity.

Key words: 2-cyanoacrylate, herbicidal activity, 4,5-dihydro-1,3,4-thiadiazol-5-one