Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (1): 82-86.doi: 10.1007/s40242-014-3203-2

• Articles • Previous Articles     Next Articles

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).

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