2-[4-(4-Chloro-benzyloxy)-2-fluoro-5-nitro-phenyl]-4-difluoromethyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one | 192938-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[4-(4-Chloro-benzyloxy)-2-fluoro-5-nitro-phenyl]-4-difluoromethyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one
• 英文别名: 2-[4-[(4-Chlorophenyl)methoxy]-2-fluoro-5-nitrophenyl]-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one
• CAS: 192938-76-4
• 化学式: C₁₇H₁₂ClF₃N₄O₄
• 分子量: 428.755
• InChiKey: CMDPFILGFSRLKG-UHFFFAOYSA-N

物化性质

• 沸点：
  516.9±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[4-(4-Chloro-benzyloxy)-2-fluoro-5-nitro-phenyl]-4-difluoromethyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one 在 吡啶 、 水 、 铁粉 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 N-[2-(4-Chloro-benzyloxy)-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-4-fluoro-phenyl]-methanesulfonamide
  参考文献：
  名称：

  Structure-Activity Relationships of Herbicidal Aryltriazolinones

  摘要：

  A series of substituted aryltriazolinones, known to inhibit protoporphyrinogen oxidase, were prepared and their structure-activity requirements at positions 4 and 5 of the aromatic ring investigated. A QSAR equation obtained for substituents at the 5 position identified the hydrophobicity term pi and the Sterimol minimum width B-1 as the two parameters affecting in-vitro biological activity. Greenhouse pre-emergence activity correlated with in-vitro activity and the hydrophobicity term pi of the substituent at that position. It was found that the phenoxy-4-oxyacetate group at aromatic position 5 was an outlier and had to be considered separately. SAR analysis of substituents at aromatic position 4 revealed that two different models were required to explain all observed substituent effects. In the first model, where the 5 position was occupied by hydrogen, the 4-chlorobenzyloxy group at aromatic position 4 gave the best compound. The second model, where the 5 position of the aromatic ring was occupied by a group other than hydrogen, resulted in a OSAR equation, previously derived, which links substituent effects at position 4 with pi and with the electronic para inductive term F-p. In this model the chloro group provides optimum biological activity. The need to separate the aryltriazolinone herbicides into several different classes in order to explain their substituent effects at aromatic positions 4 and 5 could be rationalized if more than one binding conformation, within the same binding site, is possible.

  DOI：

  10.1002/(sici)1096-9063(199708)50:4<283::aid-ps600>3.0.co;2-l
• 作为产物：
  描述：

  1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one 在 硫酸 、 硝酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2-[4-(4-Chloro-benzyloxy)-2-fluoro-5-nitro-phenyl]-4-difluoromethyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  Structure-Activity Relationships of Herbicidal Aryltriazolinones

  摘要：

  A series of substituted aryltriazolinones, known to inhibit protoporphyrinogen oxidase, were prepared and their structure-activity requirements at positions 4 and 5 of the aromatic ring investigated. A QSAR equation obtained for substituents at the 5 position identified the hydrophobicity term pi and the Sterimol minimum width B-1 as the two parameters affecting in-vitro biological activity. Greenhouse pre-emergence activity correlated with in-vitro activity and the hydrophobicity term pi of the substituent at that position. It was found that the phenoxy-4-oxyacetate group at aromatic position 5 was an outlier and had to be considered separately. SAR analysis of substituents at aromatic position 4 revealed that two different models were required to explain all observed substituent effects. In the first model, where the 5 position was occupied by hydrogen, the 4-chlorobenzyloxy group at aromatic position 4 gave the best compound. The second model, where the 5 position of the aromatic ring was occupied by a group other than hydrogen, resulted in a OSAR equation, previously derived, which links substituent effects at position 4 with pi and with the electronic para inductive term F-p. In this model the chloro group provides optimum biological activity. The need to separate the aryltriazolinone herbicides into several different classes in order to explain their substituent effects at aromatic positions 4 and 5 could be rationalized if more than one binding conformation, within the same binding site, is possible.

  DOI：

  10.1002/(sici)1096-9063(199708)50:4<283::aid-ps600>3.0.co;2-l