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高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (1): 82-86.doi: 10.1007/s40242-014-3203-2

• Articles • 上一篇    下一篇

Synthesis and Herbicidal Activities of 2-Methylpropan-2-aminium O-Methyl 1-(Substituted Phenoxyacetoxy)alkylphosphonates

PENG Hao, DENG Xiaoyan, GAO Ling, TAN Xiaosong, HE Hongwu   

  1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
  • 收稿日期:2013-05-07 修回日期:2013-06-05 出版日期:2014-02-01 发布日期:2013-06-24
  • 通讯作者: HE Hongwu,E-mail:he1208@mail.ccnu.edu.cn E-mail:he1208@mail.ccnu.edu.cn
  • 基金资助:

    Supported by the National Basic Research Program of China(No.2010CB126100), the National Key Technologies R&D Progaram of China(No.2011BAE06B03), the National Natural Science Foundation of China(No.21172090) and the Program for Changjiang Scholars and Innovative Research Team in University, China(No.IRT0953).

Synthesis and Herbicidal Activities of 2-Methylpropan-2-aminium O-Methyl 1-(Substituted Phenoxyacetoxy)alkylphosphonates

PENG Hao, DENG Xiaoyan, GAO Ling, TAN Xiaosong, HE Hongwu   

  1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
  • Received:2013-05-07 Revised:2013-06-05 Online:2014-02-01 Published:2013-06-24
  • Contact: HE Hongwu,E-mail:he1208@mail.ccnu.edu.cn E-mail:he1208@mail.ccnu.edu.cn
  • Supported by:

    Supported by the National Basic Research Program of China(No.2010CB126100), the National Key Technologies R&D Progaram of China(No.2011BAE06B03), the National Natural Science Foundation of China(No.21172090) and the Program for Changjiang Scholars and Innovative Research Team in University, China(No.IRT0953).

摘要：

A series of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates (5a―5o) was selectively synthesized by reacting the corresponding O,O-dimethyl 1-(substituted phenoxyacetoxy)-alkylphosphonates with an excess of 2-methylpropan-2-amine. The results of preliminary bioassays show that the title compounds exhibit moderate to good herbicidal activities against Brassica napus and Echinochloa crusgalli. Furthermore, compounds 5a―5j, which show much higher activities than compounds 5k―5o, were selected to further evaluate their post-emergence herbicidal activity at a dosage of 150 g/ha(1 ha=10000 m2). Especially, 2-methylpropan-2-aminium O-methyl 1-[2-(4-chloro-2-methylphenoxy)acetoxy]butylphosphonate(5h) shows 100% inhibitory effect on the growth of Brassica juncea and Amaranthus retroflexus, which is comparable with the commercial herbicide 2,4-dichlorophenoxy acetic acid(2,4-D).

关键词: Herbicidal activity, Phosphonate, 2-Methylpropan-2-aminium

Abstract:

A series of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates (5a―5o) was selectively synthesized by reacting the corresponding O,O-dimethyl 1-(substituted phenoxyacetoxy)-alkylphosphonates with an excess of 2-methylpropan-2-amine. The results of preliminary bioassays show that the title compounds exhibit moderate to good herbicidal activities against Brassica napus and Echinochloa crusgalli. Furthermore, compounds 5a―5j, which show much higher activities than compounds 5k―5o, were selected to further evaluate their post-emergence herbicidal activity at a dosage of 150 g/ha(1 ha=10000 m2). Especially, 2-methylpropan-2-aminium O-methyl 1-[2-(4-chloro-2-methylphenoxy)acetoxy]butylphosphonate(5h) shows 100% inhibitory effect on the growth of Brassica juncea and Amaranthus retroflexus, which is comparable with the commercial herbicide 2,4-dichlorophenoxy acetic acid(2,4-D).

Key words: Herbicidal activity, Phosphonate, 2-Methylpropan-2-aminium