有机化学 ›› 2014, Vol. 34 ›› Issue (1): 118-125.DOI: 10.6023/cjoc201307017 上一篇    下一篇

研究论文

N-氮杂环甲氧基-O-(4-芳氧基苯基)乳酸酰胺的合成与除草活性

刘祈星a,b, 黄明智b, 柳爱平b, 聂思桥b, 雷满香b, 任叶果b, 裴晖b, 何丽英b, 胡礼b, 胡艾希a   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007
  • 收稿日期:2013-07-12 修回日期:2013-09-12 出版日期:2014-01-25 发布日期:2013-09-30
  • 通讯作者: 柳爱平,胡艾希 E-mail:llaappliu@sina.cn; axhu@hnu.edu.cn
  • 基金资助:

    国家重点基础研究发展计划(97计划,No. 2010CB126104);国家教育部博士点专项基金(No. 20040532002);湖南省自然科学基金(No. 11JJ2006)资助项目.

Synthesis and Herbicidal Activity of Novel N-Hetrocyclo Containing Nitrogen Methoxy-O-(4-aryloxy-phenyl) Lactamide Derivatives

Liu Qixinga,b, Huang Mingzhib, Liu Aipingb, Nie Siqiaob, Lei Manxiangb, Ren Yeguob, Pei Huib, He Liyingb, Hu Lib, Hu Aixia   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007
  • Received:2013-07-12 Revised:2013-09-12 Online:2014-01-25 Published:2013-09-30
  • Supported by:

    Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126104), the National Research Foundation for the Doctoral Program of Higher Education of China (No. 20040532002), the Natural Science Foundation of Hunan Province (No. 11JJ2006).

以A8169为先导,设计并合成了12个新型的N-氮杂环甲氧基-O-(4-芳氧基苯基)乳酸酰胺化合物,其结构经1H NMR,13C NMR,LC/MS和IR确证. 初步生物活性测定结果表明,化合物在2250 g/ha剂量下,对单子叶杂草马唐(Digitaria sanguinalis)、稗草(Echinochloa crus-galli)、狗尾草(Setaria viridis)等均具有100%的除草活性,进一步活性筛选发现,(R)-(+)-N-[(2-氯噻唑-5-基)甲氧基]-O-[4-((6-氯喹喔啉-2-基)氧基)苯氧基]乳酸酰胺(2f)除草活性(马唐IC50=6.8 g/ha,稗草IC50=6.6 g/ha)远高于同类商品化除草剂炔草酯和先导化合物A8169.

关键词: N-氮杂环甲氧基-O-(4-芳氧基苯基)乳酸酰胺, 合成, 除草活性

The lead compound A8169 was modified, 12 N-hetrocyclo containing nitrogen methoxy-O-(4-aryloxy-phenyl) lactamide derivatives were designed and synthesized, and their structures were characterized by 1H NMR, 13C NMR, LC/MS and IR. The bioassay results indicated that all compounds exhibited 100% activities against Digitaria sanguinalis, Echinochloa crus-galli L and Setaria Viridis at 2250 g/ha. In particular, (R)-(+)-N-((2-chlorothiazol-5-yl)methoxy)-O-(4-((6-chloro-quinoxalin-2-yl)oxy)phenoxy) lactamide (2f) was much more effective against Digitaria sanguinalis (IC50=6.8 g/ha) and Echinochloa crus-galli (IC50=6.6 g/ha) than commercial clodinafop-propargyl and lead compound A8169.

Key words: N-hetrocyclo containing nitrogen methoxy-O-(4-aryloxy-phenyl) lactamide, synthesis, herbicidal activity