1-(4-氯苯基)-4,5-二氢-5-(3-硝基苯基)-1H-1,2,3-三唑 | 10480-24-7

• 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: 1-(4-氯苯基)-4,5-二氢-5-(3-硝基苯基)-1H-1,2,3-三唑
• 英文名称: 1-(4-Chlor-phenyl)-5-(3-nitro-phenyl)-1,2,3-triazol
• 英文别名: 1-(4-chloro-phenyl)-5-(3-nitro-phenyl)-4,5-dihydro-1H-[1,2,3]triazole；1-(4-Chlorophenyl)-5-(3-nitrophenyl)-4,5-dihydrotriazole
• CAS: 10480-24-7
• 化学式: C₁₄H₁₁ClN₄O₂
• 分子量: 302.72
• InChiKey: KCDARQHVWXTOBW-UHFFFAOYSA-N

物化性质

• 沸点：
  449.2±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 N-(m-nitrobenzylidene)-p-chloroaniline 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(4-氯苯基)-4,5-二氢-5-(3-硝基苯基)-1H-1,2,3-三唑
  参考文献：
  名称：

  Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation

  摘要：

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.

  DOI：

  10.1002/ps.2780420407

文献信息

• Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation
  作者：Pankaja K. Kadaba

  DOI：10.1002/ps.2780420407

  日期：1994.12

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.