Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 92-99.DOI: 10.6023/cjoc201408017 Previous Articles     Next Articles



王鑫, 王朝强, 傅翠蓉, 邹小毛   

  1. 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 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2014-08-14 修回日期:2014-10-10 发布日期:2014-10-16
  • 通讯作者: 邹小毛
  • 基金资助:

    国家自然科学基金(Nos. 20772067, 21472102)资助项目.

Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group

Wang Xin, Wang Chaoqiang, Fu Cuirong, Zou Xiaomao   

  1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemcal Engineering (Tianjin) Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2014-08-14 Revised:2014-10-10 Published:2014-10-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20772067, 21472102).

Two series of 2-cyano-3-(2-substituted phenyoxypyridin-5-yl) amino acrylates containing phenoxyl group were synthesized as photosynthesis II (PSII) electron transport inhibitors using 2-cyano-3-(pyridin-3-yl)aminoarylates as parent compound, in order to investigate how the different phenoxyl group on the two key sites of the parent compound affects their bioactivity. The bioassay results show that both the two series compounds exhibit certain herbicidal activity, and several compounds display > 90% fresh weight inhibit rate for broadleaf weeds (Brassica campestris L) at 1.5 kg/ha after post treatment. View from the structure-activity relationship, it can be primarily speculated that the contribution of different phenoxyl group on the aminopyridinyl of the 3-position on the cyano acrylate to the herbicidal activity is equal to that of their parent groups (aminopyridinyl groups) and their selectivity is much better than that of their parent compounds. The contribution of different phenoxyl group on the ester-site to the herbicidal activity of their parent compound is insufficient.

Key words: inhibitors of PS II electron transport, substituted phenoxypyridinyl, 2-cyanoacrylates, herbicidal activity, structure-activity relationship