新型含取代吡啶结构的氰基丙烯酸酯类化合物的合成与除草活性研究
收稿日期: 2016-11-23
修回日期: 2016-12-08
网络出版日期: 2016-10-11
基金资助
国家自然科学基金（No.21372135）、江苏省“六大人才高峰”（No.2013-SWYY-013）和江苏省大学生创新训练计划（No.201610304047Z）资助项目.
Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety
Received date: 2016-11-23
Revised date: 2016-12-08
Online published: 2016-10-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201610304047Z).
为了从氰基丙烯酸酯类化合物中寻找新的活性物质，运用活性亚结构拼接方法，设计并合成了一系列未见文献报道的新型含取代吡啶结构的氰基丙烯酸酯类衍生物.通过1H NMR，13C NMR和元素分析确认了目标化合物的结构.初步的生物活性测试结果表明，在测试浓度为1500 g·ha-1时，2-氰基-3-甲硫基-3-[4-（5-三氟甲基吡啶-2-胺基）]苯甲基胺基丙烯酸（2-甲氧基）乙酯（7l）对芥菜的茎叶处理除草活性为95%，2-氰基-3-甲硫基-3-[4-（5-三氟甲基吡啶-2-胺基）]苯甲基胺基丙烯酸[2-（2，4-二氟苯氧基）]乙酯（7e），7l和2-氰基-3-甲硫基-3-[4-（5-三氟甲基吡啶-2-胺基）]苯甲胺基丙烯酸（2-乙氧基）乙酯（7m）对繁缕的茎叶处理除草活性分别为80%，80%和100%，此外，2-氰基-3-甲硫基-3-[4-（5-三氟甲基吡啶-2-胺基）]苯甲基胺基丙烯酸[2-（2-氟苯氧基）]乙酯（7b），7l和7m对小藜的茎叶处理除草活性均达100%.
戴红 , 陈佳 , 洪宇 , 袁斌颖 , 陈雨蒙 , 石玉军 , 马瑞媛 , 梁志鹏 , 石健 . 新型含取代吡啶结构的氰基丙烯酸酯类化合物的合成与除草活性研究[J]. 有机化学, 2017 , 37(3) : 739 -745 . DOI: 10.6023/cjoc201611029
In order to find new cyanoacrylate lead compounds, a series of novel cyanoacrylates containing substituted pyridyl moiety were prepared by the method of active substructure combination. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and elemental analyses. Preliminary bioassay data displayed that in postemergence treatment 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino(2-methoxy)ethyl ester (7l) had 95% herbicidal activity against Brassica juncea at 1500 g/ha and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-[2-(2,4-difluorophenoxy)]ethyl ester (7e), 7l and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-(2-ethoxy)ethyl ester (7m) showed 80%, 80% and 100% herbicidal activity against Stellaria media, respectively. Additionally, 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino[2-(2-fluorophenoxy)]ethyl ester (7b), 7l and 7m all exhibited 100% herbicidal activity against Chenopodium serotinum L. at 1500 g/ha.
Key words： pyridine; cyanoacrylate; synthesis; herbicidal activity
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