2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate | 178273-91-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate
• 英文别名: (2-formamido-5,6-dimethylpyrimidin-4-yl) N,N-dimethylcarbamate
• CAS: 178273-91-1
• 化学式: C₁₀H₁₄N₄O₃
• 分子量: 238.246
• InChiKey: HCVMATMASZDREP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  脱甲基-抗蚜威 在 phosphate buffer 作用下， 以 水 为溶剂， 生成 2-(amino)-5,6-dimethylpyrimidin-4-yldimethylcarbamate 、 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate
  参考文献：
  名称：

  Photodegradation of Pesticides. Photolysis Rates and Half-Life of Pirimicarb and Its Metabolites in Reactions in Water and in Solid Phase

  摘要：

  The photodegradation of Pirimicarb under three different artificial lights and sunlight was studied in water solutions (buffers pH 5, 6, and 7) and in solid phase. Five photocompounds were formed in solution and two in solid phase. Pirimicarb undergoes fast degradation under all conditions. In buffer solutions it first gave three compounds with a kinetic parallel process. These compounds were assigned the structures of 2-[(methylformyl)amino]-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (II), 2-(methylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (III), and 2-(dimethylamino)-5,6-dimethyl-4-hydroxypyrimidine (V). V and II were stable to further photolysis (the latter with t(1/2) = 849 h) where as III undergoes further degradation to 2-amino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IV), and to 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IX). Both compounds were photodegraded to undetectable species, and IX shows a very high t(1/2) (48 h). A different behavior was found in solid phase, and only II and III were formed. A kinetic parallel process was demonstrated. The environmental t(1/2) and t(1/100) calculated for Pirimicarb and its photoproducts suggest their reduced persistence in natural waters.

  DOI：

  10.1021/jf9501711

文献信息

• Photocatalytic oxidation of pirimicarb in aqueous slurries containing binary and ternary oxides of zinc and titanium
  作者：José Fenoll、Isabel Garrido、Pilar Hellín、Pilar Flores、Nuria Vela、Simón Navarro

  DOI：10.1016/j.jphotochem.2014.10.014

  日期：2015.2

  The photocatalytic degradation of pirimicarb in pure water has been studied using zinc oxide (ZnO), titanium dioxide (TiO2) and zinc titanates (Zn2TiO4 and ZnTiO3) under artificial light (300-460 nm) irradiation. Comparison of catalysts showed that TiO2 is the most efficient for the removal of pirimicarb and their transformation products. To obtain a better understanding of the mechanistic details of these ZnO-TiO2-assisted photodegradation of pirimicarb, the transformation products of the processes were identified by liquid chromatography tandem mass spectrometry (LC-MS2) and liquid chromatography time of flight mass spectrometry (LC-TOF/MS) techniques. The probable photodegradation pathways are proposed and discussed. The main steps involved: N-dealkylation of the 2-dimethylamino group to form the carbamate and decarbamoylation of the carbamate moiety with further N-dealkylation of the 2-dimethylamino group to have the hydroxypyrimidines. (C) 2014 Elsevier B.V. All rights reserved.
• Photodegradation of Pesticides. Photolysis Rates and Half-Life of Pirimicarb and Its Metabolites in Reactions in Water and in Solid Phase
  作者：Filippo M. Pirisi、Paolo Cabras、V. Luigi Garau、Marinella Melis、Enrico Secchi

  DOI：10.1021/jf9501711

  日期：1996.1.1

  The photodegradation of Pirimicarb under three different artificial lights and sunlight was studied in water solutions (buffers pH 5, 6, and 7) and in solid phase. Five photocompounds were formed in solution and two in solid phase. Pirimicarb undergoes fast degradation under all conditions. In buffer solutions it first gave three compounds with a kinetic parallel process. These compounds were assigned the structures of 2-[(methylformyl)amino]-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (II), 2-(methylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (III), and 2-(dimethylamino)-5,6-dimethyl-4-hydroxypyrimidine (V). V and II were stable to further photolysis (the latter with t(1/2) = 849 h) where as III undergoes further degradation to 2-amino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IV), and to 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IX). Both compounds were photodegraded to undetectable species, and IX shows a very high t(1/2) (48 h). A different behavior was found in solid phase, and only II and III were formed. A kinetic parallel process was demonstrated. The environmental t(1/2) and t(1/100) calculated for Pirimicarb and its photoproducts suggest their reduced persistence in natural waters.