含吡啶甲基苯基醚结构的氰基丙烯酸酯类化合物的合成及除草活性研究  

Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties

作　　者：吴姗姗[1,2] 苗文科[1,3] 王婷婷[1] 方建新[1] 

机构地区：[1]南开大学元素有机化学国家重点实验室,天津300071 [2]国家知识产权局专利局专利审查协作江苏中心,苏州215011 [3]南开大学功能高分子材料教育部重点实验室,天津300071

出　　处：《有机化学》2015年第7期1484-1492,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20772068)资助项目~~

摘　　要：以氰基丙烯酸酯类化合物为母体结构,利用生物等排原理和活性亚结构拼接的方法设计并合成了2个系列新型含吡啶甲基苯基醚结构的2-氰基丙烯酸酯类化合物2-氰基-3-[4-(2-氯吡啶-5)-甲氧基]苯甲胺基-3-烷(硫)基丙烯酸酯.所有化合物的结构均通过1H NMR、13C NMR、元素分析或者高分辨质谱确证.生物活性测试结果表明,部分化合物显示出较好的除草活性,其中化合物13e和13g,在剂量为375 g/ha时对油菜茎叶处理的抑制率达到100%;当剂量为187.5g/ha时,化合物13e对油菜茎叶处理的抑制率仍然达到100%.构效关系研究发现苯环上取代基的位阻效应和电子效应能够显著地影响该类化合物的除草活性.Two series of 2-cyanoacrylates containing 4-（6-chloropyridin-3-yl）methoxy-benzylamine moieties were synthesized as herbicides using 2-cyano-3-（pyridine-3-yl）aminoacrylates as precursor compound. The structures were confirmed by 1H NMR, 13C NMR, Elemental Analysis or High-Resolution Mass spectrometry （HRMS）. The herbicidal activity tests showed that most of the target compounds had good inhibition towards dicotyledonous weeds. Compounds 13e and 13g showed 100% herbicidal activity at the dose of 375g/ha against rape, and compound 13e showed 100% herbicidal activity against rape even at the dose of 187.5 g/ha. From the structure-activity relationship study, it can be primarily concluded that both the contributions of the electronic and steric effects of the phenyl group are very important to the herbicidal activity.

关 键 词：2-氰基丙烯酸酯 4-(6-氯吡啶-3-基)甲氧基苄胺 除草活性 构效关系 

分 类 号：TQ450.1[化学工程—农药化工]