Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 109-120.DOI: 10.6023/cjoc201408012 Previous Articles     Next Articles



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 发布日期:2014-10-13
  • 通讯作者: 胡方中
  • 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 Published:2014-10-13
  • Supported by:

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

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