Methyl 1-{N-methyl-N-[N-(N,N-iminoxycarbonyldimethylcarbamoyl(thiomethyl)methylene)iminoxycarbonyl]-aminomethoxy}-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate | 164031-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 1-{N-methyl-N-[N-(N,N-iminoxycarbonyldimethylcarbamoyl(thiomethyl)methylene)iminoxycarbonyl]-aminomethoxy}-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[[(Z)-[2-(dimethylamino)-1-methylsulfanyl-2-oxoethylidene]amino]oxycarbonyl-methylamino]methoxy]oxane-2-carboxylate
• CAS: 164031-87-2
• 化学式: C₂₁H₃₁N₃O₁₃S
• 分子量: 565.555
• InChiKey: OMVXOXJYMNLXJF-IWKQTSDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Methyl 1-{N-methyl-N-[N-(N,N-iminoxycarbonyldimethylcarbamoyl(thiomethyl)methylene)iminoxycarbonyl]-aminomethoxy}-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 在 sacharic acid 1,4-lactone 、 immobilized rabbit liver microsome enzyme 、 sodium methylate 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 反应 0.17h， 生成 1-{N-Methyl-N-[N-(N,N-dimethylcarbamoyl(thiomethyl)methylene)iminoxycarbonyl]aminomethoxy}-β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Phloem mobility of xenobiotics VI. A phloem-mobile pro-nematicide based on oxamyl exhibiting root-specific activation in transgenic tobacco

  摘要：

  AbstractPhloem mobility is a desirable attribute for pesticides in many applications, and the physicochemical properties necessary for phloem mobility are now well understood. However, attempts to derivatize pesticides to make them phloem mobile are often frustrated by a concomitant loss of activity. This study describes a phloem‐mobile pro‐nematicide, a hydroxymethyloxamyl glucuronide (JR522) coupled with an in‐situ activation mechanism in transgenic tobacco expressing Escherichia coli β‐glucuronidase in its root tips. When applied foliarly to the transgenic tobacco, JR522 and its methyl ester (JM775) showed greater nematicidal activity than oxamyl against root‐knot nematodes. This example of combining pro‐pesticide chemistry with crop genetic engineering for site‐specific activation provides a model system for demonstrating how to circumvent the often mutual exclusivity of phloem mobility and pesticidal activity. Additional advantages of this scheme include the potential mammalian safety of the propesticide, as exhibited by JR522 in this study, and a high degree of site‐specific release of xenobiotics in plants.

  DOI：

  10.1002/ps.2780440103
• 作为产物：
  描述：

  oxamyl 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 Methyl 1-{N-methyl-N-[N-(N,N-iminoxycarbonyldimethylcarbamoyl(thiomethyl)methylene)iminoxycarbonyl]-aminomethoxy}-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate
  参考文献：
  名称：

  Phloem mobility of xenobiotics VI. A phloem-mobile pro-nematicide based on oxamyl exhibiting root-specific activation in transgenic tobacco

  摘要：

  AbstractPhloem mobility is a desirable attribute for pesticides in many applications, and the physicochemical properties necessary for phloem mobility are now well understood. However, attempts to derivatize pesticides to make them phloem mobile are often frustrated by a concomitant loss of activity. This study describes a phloem‐mobile pro‐nematicide, a hydroxymethyloxamyl glucuronide (JR522) coupled with an in‐situ activation mechanism in transgenic tobacco expressing Escherichia coli β‐glucuronidase in its root tips. When applied foliarly to the transgenic tobacco, JR522 and its methyl ester (JM775) showed greater nematicidal activity than oxamyl against root‐knot nematodes. This example of combining pro‐pesticide chemistry with crop genetic engineering for site‐specific activation provides a model system for demonstrating how to circumvent the often mutual exclusivity of phloem mobility and pesticidal activity. Additional advantages of this scheme include the potential mammalian safety of the propesticide, as exhibited by JR522 in this study, and a high degree of site‐specific release of xenobiotics in plants.

  DOI：

  10.1002/ps.2780440103