有机化学 ›› 2015, Vol. 35 ›› Issue (1): 92-99.DOI: 10.6023/cjoc201408017 上一篇    下一篇

研究论文

新型含取代苯氧基的2-氰基-3-(2-取代吡啶-5-基)氨基丙烯酸酯类化合物的合成及除草活性

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 出版日期:2015-01-25 发布日期:2014-10-16
  • 通讯作者: 邹小毛 E-mail:xmzou@nankai.edu.cn
  • 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 Online:2015-01-25 Published:2014-10-16
  • Supported by:

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

以氰基吡啶氨基丙烯酸酯类化合物为母体, 合成了两个系列的含取代苯氧基的2-氰基-3-(2-取代吡啶-5-基)氨基丙烯酸酯化合物, 即光系统II (PSII)电子传递抑制剂, 以考察不同苯氧基在两个关键位点对其生物活性的影响. 生测结果表明: 这两个系列化合物均显示出一定的除草活性, 其中几种化合物在处理剂量为1.5 kg/ha时, 对油菜等阔叶杂草的茎叶处理后的鲜重抑制率达90%以上. 从构效关系上, 可以初步推测不同苯氧取代基位于氨基吡啶基对位上对除草活性的贡献与其母体氨基吡啶基化合物大致相当, 且选择性更好; 而在酯基部分对除草活性的贡献不明显.

关键词: 光系统II (PS-II)电子传递抑制剂, 取代苯氧吡啶基, 2-氰基丙烯酸酯, 除草活性, 构效关系

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