2-(2-(4-溴-2-氟苯基)亚肼基)丙酸 | 111992-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-(4-溴-2-氟苯基)亚肼基)丙酸
• 英文名称: 2-(2-(4-bromo-2-fluorophenyl)hydrazono)propanoic acid
• 英文别名: 2-[(4-Bromo-2-fluorophenyl)hydrazinylidene]propanoic acid
• CAS: 111992-08-6
• 化学式: C₉H₈BrFN₂O₂
• 分子量: 275.077
• InChiKey: STIATQSOKRTBKH-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C
• 沸点：
  358.7±52.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(4-溴-2-氟苯基)亚肼基)丙酸 在 硫酸 、 叠氮磷酸二苯酯 、 四丁基溴化铵 、 硝酸 、 铁粉 、 potassium carbonate 、 氯化铵 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 9.17h， 生成 1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1-(6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with K-i values ranging from 0.06 to 17.79 mu M. Compound 2e, ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with K-i value of 0.06 mu M against mtPPO, comparable to (K-i = 0.03 mu M) sulfentrazone. Further green house assays showed that compound 2f (K-i = 0.24 mu M, mtPPO), ethyl 2-{[5-(4(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio}propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.056
• 作为产物：
  描述：

  4-溴-2-氟苯胺 、 丙酮酸 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 以 水 为溶剂， 反应 2.08h， 以88%的产率得到2-(2-(4-溴-2-氟苯基)亚肼基)丙酸
  参考文献：
  名称：

  Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1-(6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with K-i values ranging from 0.06 to 17.79 mu M. Compound 2e, ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with K-i value of 0.06 mu M against mtPPO, comparable to (K-i = 0.03 mu M) sulfentrazone. Further green house assays showed that compound 2f (K-i = 0.24 mu M, mtPPO), ethyl 2-{[5-(4(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio}propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.056