Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 215-219.DOI: 10.6023/cjoc201308014 Previous Articles     Next Articles

Articles

O-烷基α-(取代苯氧乙酰氧基)烃基膦酸盐的合成与生物活性

王涛, 邹鹏, 彭浩, 贺红武   

  1. 华中师范大学化学学院 教育部农药与化学生物学重点实验室 武汉 430079
  • 收稿日期:2013-08-12 修回日期:2013-09-06 发布日期:2013-09-25
  • 通讯作者: 贺红武 E-mail:he1208@mail.ccnu.edu.cn
  • 基金资助:

    国家重点基础研究发展规划(973计划,No.2010CB126100);国家自然科学基金(No. 21172090);教育部创新团队(No. IRT0953)资助项目.

Synthesis and Biological Activity of O-Alkyl α-(Substituted phenoxyacetoxy)alkylphosphonate

Wang Tao, Zou Peng, Peng Hao, He Hongwu   

  1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemitry Central China Normal University, Wuhan 430079
  • Received:2013-08-12 Revised:2013-09-06 Published:2013-09-25
  • Supported by:

    Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126100), the National Natural Science Foundation of China (No. 21172090) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT, No. IRT0953).

For the purpose of studying the structure-activity relationship of O-alkyl α-(substituted phenoxyacetoxy)alkylphosphonic derivatives, fourteen novel O-alkyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized by the reactions of key intermediate 3 with NaI or LiBr. The intermediate 3 was prepared by the treatment of α-hydroxyalkylphosphonates 1 with substituted phenoxyacetyl chlorides 2 which could be easily obtained by the reaction of substituted phenoxyacetic acids with excess thionyl chloride. The structures of compounds 4 have been confirmed by 1H NMR, IR, MS and elemental analyses. The results of preliminary bioassay indicated that most of title compounds possess significant herbicidal and fungicidal activities. Compound 4a showed 100% inhibitory activity against all the tested species in the rate of 1.5 kg/ha. Compounds 4h4m exhibited more than 90% inhibitory activity against Sclerotinia sclerotiorum and Botrytis cinerea in the rate of 50 μg/g.

Key words: synthesis, phosphonate, herbicidal activity, fungicidal activity