(S)-2-[5-(4-Chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-2-nitro-phenylamino]-3-methyl-butyric acid | 155674-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[5-(4-Chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-2-nitro-phenylamino]-3-methyl-butyric acid
• CAS: 155674-41-2
• 化学式: C₁₆H₁₆ClF₃N₄O₅
• 分子量: 436.775
• InChiKey: JSBWWNOYRPDJBA-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119.52
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[5-(4-Chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-2-nitro-phenylamino]-3-methyl-butyric acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 AH 2.442
  参考文献：
  名称：

  Enantioselectivity of protoporphyrinogen oxidase-inhibiting herbicides

  摘要：

  AbstractProtoporphyrinogen oxidase (Protox) was inhibited stereoselectively by three pairs of enantiomers belonging to diphenyl ether (DPE) and pyrazole phenyl ether (PPE) herbicide classes. The (R) enantiomers were 10‐ to 44‐fold more active than the (S) enantiomers as inhibitors of Protox from barley etioplasts. Similarly, the (R) enantiomers caused green barley tissue to accumulate greater amounts of porphyrins and caused greater tissue damage than the (S) enantiomers. The (R) enantiomers competed more successfully with [ 14 C]acifluorfen than the (S) enantiomers for the binding sites on Protox. In the PPE class, the in‐vitro and in‐vivo activity differences were wider in the isopropyl pairs than in the n‐propyl pairs. The DPE enantiomers were tested on ten dicotyledonous and six monocotyledonous weed species and ten crops for weed control and crop safety. In general, neither enantiomer had pre‐emergence activity on monocotyledons, but the (R) enantiomer provided some monocotyledonous weed control when applied post‐emergence. On dicotyledons, the (R) enantiomer provided excellent pre‐emergence control, whereas the (S) enantiomer was inactive. The (R) enantiomer caused no injury to corn, cotton, peanuts, rice, sorghum, or soybeans applied pre‐emergence, but it severely injured crops when applied post‐emergence. There was a positive correlation between the activities of the compounds at the molecular, cellular and whole plant levels. The only molecular property differences found to account for differences in activity between members of chiral pairs were steric parameters.

  DOI：

  10.1002/ps.2780400404
• 作为产物：
  描述：

  L-缬氨酸 、 4-Chloro-3-(3-fluoro-4-nitro-phenoxy)-1-methyl-5-trifluoromethyl-1H-pyrazole 在 copper (II)-fluoride potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 生成 (S)-2-[5-(4-Chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-2-nitro-phenylamino]-3-methyl-butyric acid
  参考文献：
  名称：

  Enantioselectivity of protoporphyrinogen oxidase-inhibiting herbicides

  摘要：

  AbstractProtoporphyrinogen oxidase (Protox) was inhibited stereoselectively by three pairs of enantiomers belonging to diphenyl ether (DPE) and pyrazole phenyl ether (PPE) herbicide classes. The (R) enantiomers were 10‐ to 44‐fold more active than the (S) enantiomers as inhibitors of Protox from barley etioplasts. Similarly, the (R) enantiomers caused green barley tissue to accumulate greater amounts of porphyrins and caused greater tissue damage than the (S) enantiomers. The (R) enantiomers competed more successfully with [ 14 C]acifluorfen than the (S) enantiomers for the binding sites on Protox. In the PPE class, the in‐vitro and in‐vivo activity differences were wider in the isopropyl pairs than in the n‐propyl pairs. The DPE enantiomers were tested on ten dicotyledonous and six monocotyledonous weed species and ten crops for weed control and crop safety. In general, neither enantiomer had pre‐emergence activity on monocotyledons, but the (R) enantiomer provided some monocotyledonous weed control when applied post‐emergence. On dicotyledons, the (R) enantiomer provided excellent pre‐emergence control, whereas the (S) enantiomer was inactive. The (R) enantiomer caused no injury to corn, cotton, peanuts, rice, sorghum, or soybeans applied pre‐emergence, but it severely injured crops when applied post‐emergence. There was a positive correlation between the activities of the compounds at the molecular, cellular and whole plant levels. The only molecular property differences found to account for differences in activity between members of chiral pairs were steric parameters.

  DOI：

  10.1002/ps.2780400404