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

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

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1HNMR,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1.5kg/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.

A series of novel 2-cyanoacrylates containing a 4,5-dihydro-5-oxo1,3,4-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 dicotyledonous weeds. Compound 6j showed the highest herbicidal activity at the dose of 1.5 kg/ha with 100% inhibition 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.