有机化学 ›› 2017, Vol. 37 ›› Issue (2): 526-532.DOI: 10.6023/cjoc201608018 上一篇    下一篇

研究简报

新型吡啶氧基苯胺基丙酸/乙酸乙酯的合成以及除草活性研究

徐志红a, 张涛b, 王少康b, 李俊凯a   

  1. a 长江大学 主要粮食作物产业化湖北省协同创新中心 荆州 434205;
    b 长江大学农学院 荆州 434205
  • 收稿日期:2016-08-23 修回日期:2016-09-06 发布日期:2016-10-09
  • 通讯作者: 李俊凯 E-mail:junkaili@sina.com
  • 基金资助:

    国家自然科学基金(No.31301976)和主要粮食作物产业化湖北省协同创新中心开放基金资助项目.

Synthesis and Herbicidal Activities of Novel Ethyl 2-(4-(Pyridin-2-yl-oxy)phenyl-amino)propanoates/acetates

Xu Zhihonga, Zhang Taob, Wang Shaokangb, Li Junkaia   

  1. a Hubei Collaborative Innovation Center for Grain Industry, Yangtze University, Jingzhou 434205;
    b Agricutural College, Yangtze University, Jingzhou 434205
  • Received:2016-08-23 Revised:2016-09-06 Published:2016-10-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China and the Open Fund for Hubei Collaborative Innovation Center for Grain Industry.

芳氧苯氧基丙酸酯是一类以单子叶植物叶绿体内乙酰辅酶A羧化酶为作用靶标的重要除草剂.合成了23个全新的吡啶氧基苯胺基丙酸/乙酸乙酯类化合物,并通过核磁共振氢谱、高分辨质谱和X单晶衍射对新化合物结构进行了确证.测定了新化合物对稗草和油菜的室内生物活性,结果表明,新化合物对稗草具有较好的抑制作用,其中2-[4-(5-NO2-2-吡啶氧基)苯胺基]丙酸乙酯(B5)活性最高,对稗草的除草活性与对照药剂氟吡甲禾灵相当,可以作为研究新除草剂的先导化合物.

关键词: 吡啶氧基苯胺基丙酸/乙酸乙酯, 合成, 除草活性, 乙酰辅酶A羧化酶

Aryloxyphenoxypropionates (APPs) are a class of herbicides targeting on acetyl-coenzyme A carboxylase (ACCase) in monocot chloroplast. The article presents synthesis of twenty three novel ethyl 2-(4-(pyridin-2-yl-oxy)phenylamino)-propanoates/acetates, and their structures were characterized by 1H NMR, HRMS and X-ray single-crystal diffraction. The herbicidal activities on barnyard grass and rape of the novel compounds were evaluated. Ethyl 2-(4-(5-nitropyridin-2-yloxy)-phenylamino)propanoate (B5) showed almost the same level of herbicidal activity on barnyard grass as commercial herbicide fluazifop-methyl which could become a potential lead compound on weeds.

Key words: ethyl 2-(4-(pyridin-2-yl-oxy)phenylamino)propanoate/acetates, synthesis, herbicidal activity, acetyl-CoA carboxylase