1-乙基咪唑烷-2,4,5-三酮 5-(O-甲基肟) | 71342-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 1-乙基咪唑烷-2,4,5-三酮 5-(O-甲基肟)
• 中文别名: 1-乙基咪唑烷-2,4,5-三酮5-(O-甲基肟)
• 英文名称: 1-ethyl-5-methoxyimino-2,4-dioxoimidazolidine
• 英文别名: 1-Ethyl-5-methoxyiminoimidazolidine-2,4-dione
• CAS: 71342-67-1
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: IWOKFBNWXNLMMA-UHFFFAOYSA-N

物化性质

• 熔点：
  135-139°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  霜脲氰 在 Botrytis cinera 作用下， 生成 1-乙基咪唑烷-2,4,5-三酮 、 Acetamino-cyan-essigsaeure 、 1-乙基咪唑烷-2,4,5-三酮 5-(O-甲基肟) 、 1-(2,2-dimethyl-5-oxo-4-cyano-3-imidazolin-1-yl)-N-ethyl amide
  参考文献：
  名称：

  Characterization of Metabolites of Fungicidal Cymoxanil in a Sensitive Strain of Botrytis cinerea

  摘要：

  The metabolism of cymoxanil [1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea] by a very sensitive strain of Botrytis cinerea toward this fungicide was studied by using [2-(14)C]-cymoxanil. Labeled cymoxanil was added either in a culture of this strain or in its enzymatic extract. The main metabolites, detected in biological samples, were isolated and identified by mass and NMR spectrometry. Their identification allowed us to show that this strain quickly metabolized cymoxanil according to at least three enzymatic pathways: (i) cyclization leading, after hydrolysis, to ethyl parabanic acid, (ii) reduction giving demethoxylated cymoxanil, and (iii) hydrolysis and reduction followed by acetylation leading to N-acetylcyanoglycine. In a cell-free extract of the same strain, only the first and the second enzymatic reactions, quoted above, occurred. Biological tests showed that, among all the metabolites, only N-acetylcyanoglycine is fungitoxic toward this sensitive strain.

  DOI：

  10.1021/jf8010917

文献信息

• Characterization of Metabolites of Fungicidal Cymoxanil in a Sensitive Strain of Botrytis cinerea
  作者：Frederique Tellier、Rene Fritz、Lucien Kerhoas、Paul-Henri Ducrot、Jacques Einhorn、Abel Carlin-Sinclair、Pierre Leroux

  DOI：10.1021/jf8010917

  日期：2008.9.10

  The metabolism of cymoxanil [1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea] by a very sensitive strain of Botrytis cinerea toward this fungicide was studied by using [2-(14)C]-cymoxanil. Labeled cymoxanil was added either in a culture of this strain or in its enzymatic extract. The main metabolites, detected in biological samples, were isolated and identified by mass and NMR spectrometry. Their identification allowed us to show that this strain quickly metabolized cymoxanil according to at least three enzymatic pathways: (i) cyclization leading, after hydrolysis, to ethyl parabanic acid, (ii) reduction giving demethoxylated cymoxanil, and (iii) hydrolysis and reduction followed by acetylation leading to N-acetylcyanoglycine. In a cell-free extract of the same strain, only the first and the second enzymatic reactions, quoted above, occurred. Biological tests showed that, among all the metabolites, only N-acetylcyanoglycine is fungitoxic toward this sensitive strain.