有机化学 ›› 2017, Vol. 37 ›› Issue (3): 739-745.DOI: 10.6023/cjoc201611029 上一篇    下一篇

研究简报

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

戴红a, 陈佳a, 洪宇a, 袁斌颖a, 陈雨蒙a, 石玉军a, 马瑞媛a, 梁志鹏b, 石健b   

  1. a 南通大学化学化工学院 南通 226019;
    b 南通大学分析测试中心 南通 226019
  • 收稿日期:2016-11-23 修回日期:2016-12-08 发布日期:2016-10-11
  • 通讯作者: 石玉军,E-mail:yjshi2015@163.com;石健,E-mail:gaohbhe2015@aliyun.com E-mail:yjshi2015@163.com;gaohbhe2015@aliyun.com
  • 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

Dai Honga, Chen Jiaa, Hong Yua, Yuan Binyinga, Chen Yumenga, Shi Yujuna, Ma Ruiyuana, Liang Zhipengb, Shi Jianb   

  1. a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b Analysis and Testing Center, Nantong University, Nantong 226019
  • Received:2016-11-23 Revised:2016-12-08 Published:2016-10-11
  • Contact: 10.6023/cjoc201611029 E-mail:yjshi2015@163.com;gaohbhe2015@aliyun.com
  • 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),7l7m对小藜的茎叶处理除草活性均达100%.

关键词: 吡啶, 氰基丙烯酸酯, 合成, 除草活性

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