有机化学 ›› 2015, Vol. 35 ›› Issue (1): 109-120.DOI: 10.6023/cjoc201408012 上一篇    下一篇

研究论文

2-氰基-3-[1-(4-取代苯氧基苯基)乙胺基]烯酸乙氧乙酯的合成及除草活性

杨晓兵, 毕常芬, 胡方中, 狄红静, 程心心, 李丹, 阚晓丽, 马嘉雪, 邹小毛   

  1. 南开大学元素有机化学国家重点实验室 南开大学元素有机化学研究所 天津化学化工协同创新中心 天津 300071
  • 收稿日期:2014-08-12 修回日期:2014-10-08 出版日期:2015-01-25 发布日期:2014-10-13
  • 通讯作者: 胡方中 E-mail:fzhu@nankai.edu.cn
  • 基金资助:

    国家“十二五”科技支撑计划(No. 2011BAE06B03-12)资助项目.

Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates

Yang Xiaobing, Bi Changfen, Hu Fangzhong, Di Hongjing, Cheng Xinxin, Li Dan, Kan Xiaoli, Ma Jiaxue, Zou Xiaomao   

  1. State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071
  • Received:2014-08-12 Revised:2014-10-08 Online:2015-01-25 Published:2014-10-13
  • Supported by:

    Project supported by the National “Twelfth Five-Year” Plan for Science & Technology (No. 2011BAE06B03-12).

以取代苯酚4和对氟苯乙酮(5)为原料, 经4步反应合成关键中间体1-(4-取代苯氧苯基)乙胺(9), 再与3种中间体2-氰基-3-乙氧基-2-戊烯酸乙氧乙酯(1)、2-氰基-3,3-二甲硫基丙烯酸乙氧乙酯(2)和2-氰基-3-氯-4,4,4-三氟丁烯酸乙氧乙酯(3)分别发生缩合反应, 合成了3个系列共35个新2-氰基-3-[1-(4-取代苯氧基苯基)乙胺基]烯酸乙氧乙酯类化合物(10, 1112). 所有新化合物的结构均经过1H NMR, 13C NMR, 19F NMR和HRMS的确证, 并测试了目标化合物的除草活性, 部分化合物在剂量为93.75 g/ha时, 对双子叶植物油菜和苋菜的抑制率为100%.

关键词: 2-氰基烯酸酯类化合物, 苯氧基苯乙胺, 合成, 除草活性

Key intermediates, 1-(4-substitutedphenoxyphenyl)ethanamines (9), which were prepared from starting material substituted phenols 4 and p-fluoroacetophenone (5), were condensed with 2-ethoxyethyl 2-cyano-3-ethoxypent-2-enoate (1) or 2-ethoxyethyl-2-cyano-3,3-bis(methylthio)acrylate (2) or 2-ethoxyethyl-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate (3), giving three series of 2-ethoxyethyl 2-cyano-3-(1-(substitued phenoxyphenyl)ethylamino) alkenates (10, 11 and 12). All of the new compounds have been characterized by 1H NMR, 13C NMR, 19F NMR, IR and HRMS. The herbicidal activities of the title compounds were tested, which indicated that some of the title compounds showed 100% inhibition against Brassica campestris and Amaranthus retroflexus L. at a dose of 93.75 g/ha.

Key words: 2-cyanoalkenates, phenoxyphenyl ethylamine, synthesis, herbicidal activity