Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (08): 1287-1293. Previous Articles     Next Articles

Reports

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

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