O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy)-2,2,2-trichloroethylphosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy)-2,2,2-trichloroethylphosphonate
• 英文别名: (2,2,2-Trichloro-1-dimethoxyphosphorylethyl) 2-(2,4-dichlorophenoxy)acetate
• 化学式: C₁₂H₁₂Cl₅O₆P
• 分子量: 460.462
• InChiKey: DPZMZEKSCGDVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二氯苯氧乙酸 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成 O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy)-2,2,2-trichloroethylphosphonate
  参考文献：
  名称：

  Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a New Herbicide. 1. Synthesis and Herbicidal Activity of HW02 and Analogues as Novel Inhibitors of Pyruvate Dehydrogenase Complex

  摘要：

  On the basis of the previous work for optimization of O,O-diethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates, further extensive synthetic modifications were made to the substituents in alkylphosphonate and phenoxy moieties of the title compounds. New O,O-dimethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compounds were studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl alpha-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa , was found to be the most effective compound against broadleaf weeds and showed potential utility as herbicide.

  DOI：

  10.1021/jf104247w

文献信息

• Synthesis and herbicidal activities of methyl-1-(2,4-dichlorophenoxyacetoxy)alkylphosphonate monosalts
  作者：Hong Wu He、Tao Wang、Jun Lin Yuan

  DOI：10.1016/j.jorganchem.2005.01.061

  日期：2005.5

  A series of 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5 and its corresponding phosphonate monosalts 6 were synthesized as potential herbicide. The phosphonate monosalts can be prepared from 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5, which were synthesized by the condensation of O,O-dimethyl-1-hydroxyalkylphosphonates with dichlorophenoxyacetic chloride. This method provides a simple and efficient procedure for the synthesis of phosphonate derivatives containing sensitive groups to acid, base or water such as carboxylate ester bond; and the herbicidal activity of title compounds was evaluated in a set of experiments in greenhouse. Most of the compounds exhibited notable herbicidal activity. (c) 2005 Elsevier B.V. All rights reserved.