2,4-(N,N'-Diisopropyl)diamino-6-methylsulfonyl-1,3,5-triazine | 55723-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2,4-(N,N'-Diisopropyl)diamino-6-methylsulfonyl-1,3,5-triazine
• 英文别名: 1,3,5-Triazine-2,4-diamine, N,N'-bis(1-methylethyl)-6-(methylsulfonyl)-；6-methylsulfonyl-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine
• CAS: 55723-98-3
• 化学式: C₁₀H₁₉N₅O₂S
• 分子量: 273.359
• InChiKey: PMRUCNQJEZNRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-(N,N'-Diisopropyl)diamino-6-methylsulfonyl-1,3,5-triazine 在 hydroxide 作用下， 生成 扑灭津- 2 -羟基
  参考文献：
  名称：

  水溶液中次氯酸钠对metry萘的氧化作用：动力学和机理。

  摘要：

  The reaction of the herbicide prometryne (C9H16N5-S-CH3) with sodium hypochlorite has been investigated from the kinetic and mechanistic stand point. Under the fixed experimental conditions: pH = 7, T = 25 degrees C, [NaClO]/[substrate] = (10(-3) M)/(10(-5) M), prometryne oxidation takes place according to the following pathway: R-S-CH3 (P) --> R-SO-CH3 (a) --> R-SO2-CH3 (b) --> R-O-SO2-CH3 (x) --> R-OH (c), where R stands for C9H16N5, i.e., the substituted triazine ring of prometryne and (x) is an unexpected intermediate never previously detected nor identified. After having synthesized the pure intermediates (a), (b), and (x), the values of the pseudo-first-order kinetic constants of the first three steps were experimentally obtained: [k(1) = (0.64 +/- 0.03) s(-1), k(2) = (1.81 +/- 0.05) x 10(-3) S-1 k(3) = (1.50 +/- 0.03) x 10(-4) s(-1)]. As for k(4), its value [(2.5 +/- 0.2) x 10(-5) s(-1)] has been calculated indirectly on the basis of the kinetic theory concerning consecutive reactions. All the steps were pseudo-first-order reactions with respect to their specific substrate. The effect of pH on the hydrolysis of (b) [(b) --> (c)], in the absence of NaClO, has been also assessed to better elucidate the mechanism of the overall pathway.

  DOI：

  10.1021/es00012a015
• 作为产物：
  描述：

  扑草净 在 双氧水 作用下， 以 丙酮 为溶剂， 反应 22.0h， 生成 2,4-(N,N'-Diisopropyl)diamino-6-methylsulfonyl-1,3,5-triazine
  参考文献：
  名称：

  水溶液中次氯酸钠对metry萘的氧化作用：动力学和机理。

  摘要：

  The reaction of the herbicide prometryne (C9H16N5-S-CH3) with sodium hypochlorite has been investigated from the kinetic and mechanistic stand point. Under the fixed experimental conditions: pH = 7, T = 25 degrees C, [NaClO]/[substrate] = (10(-3) M)/(10(-5) M), prometryne oxidation takes place according to the following pathway: R-S-CH3 (P) --> R-SO-CH3 (a) --> R-SO2-CH3 (b) --> R-O-SO2-CH3 (x) --> R-OH (c), where R stands for C9H16N5, i.e., the substituted triazine ring of prometryne and (x) is an unexpected intermediate never previously detected nor identified. After having synthesized the pure intermediates (a), (b), and (x), the values of the pseudo-first-order kinetic constants of the first three steps were experimentally obtained: [k(1) = (0.64 +/- 0.03) s(-1), k(2) = (1.81 +/- 0.05) x 10(-3) S-1 k(3) = (1.50 +/- 0.03) x 10(-4) s(-1)]. As for k(4), its value [(2.5 +/- 0.2) x 10(-5) s(-1)] has been calculated indirectly on the basis of the kinetic theory concerning consecutive reactions. All the steps were pseudo-first-order reactions with respect to their specific substrate. The effect of pH on the hydrolysis of (b) [(b) --> (c)], in the absence of NaClO, has been also assessed to better elucidate the mechanism of the overall pathway.

  DOI：

  10.1021/es00012a015

文献信息

• Identification of disinfection by-products of selected triazines in drinking water by LC-Q-ToF-MS/MS and evaluation of their toxicity
  作者：Rikke Brix、Neus Bahi、Maria J. Lopez de Alda、Marinella Farré、Josep-Maria Fernandez、Damià Barceló

  DOI：10.1002/jms.1509

  日期：2009.3

  During the development of an on-line solid phase extraction-liquid chromatography-ultraviolet detection (SPE-LC-UV) analytical method for determination of eight selected triazines; ametryn, atrazine, cyanazine, metrybuzine, prometryn, propazin, simazine, and terbutryn, in drinking water, it was observed that the retention times of three of them (ametryn, prometryn, and terbutryn) in Milli-Q water were different from those in chlorinated Milli-Q water, indicating the formation of new products. The cause of this change was found in the oxidation of the molecules as a result of chlorination with sodium hypochlorite. Experiments performed at varying concentrations of triazines and hypochlorite showed that the extent of the reaction depended on their relative concentrations. At the maximum admissible level of 100 ng/l for individual pesticides in drinking water, no apparent transformation was observed in the absence or at low concentrations (0.05 mg/l) of hypochlorite; however, on increasing the concentration of hypochlorite to the level typically present in drinking water (0.9 mg/l) the transformation was complete. The reaction is quite fast; within 1 h the parent compound is completely degraded and after 22 h the concentrations of the by-products are constant. Investigation of the by-products by ultra performance liquid chromatography-quadrupole-time of flight- tandem mass spectrometry (UPLC-Q-ToF-MS/MS) has shown that all three triazines follow a similar transformation pathway, forming four new molecules whose structure have been elucidated. The acute toxicity of the new products was investigated using a standard method based on the bioluminescence inhibition of Vibrio fischeri, and the by-products showed a higher toxicity than that of the parent compounds. Copyright © 2008 John Wiley & Sons, Ltd.

  开发在线固相萃取-液相色谱-紫外检测（SPE-LC-UV）分析方法来测定八种选定的三嗪；饮用水中的莠灭净、莠去津、氰嗪、啶虫嗪、扑草净、扑灭嗪、西玛嗪和特丁净，观察到其中三种（莠灭净、扑草净和特丁净）在 Milli-Q 水中的保留时间与在 Milli-Q 水中的保留时间不同氯化 Milli-Q 水，表明新产品的形成。造成这种变化的原因是次氯酸钠氯化导致分子氧化。在不同浓度的三嗪和次氯酸盐下进行的实验表明，反应的程度取决于它们的相对浓度。在饮用水中各种农药的最大允许浓度为 100 纳克/升时，在次氯酸盐不存在或次氯酸盐浓度较低（0.05 毫克/升）的情况下，未观察到明显的变化；然而，当次氯酸盐浓度增加到饮用水中通常存在的水平（0.9毫克/升）时，转变就完成了。反应速度相当快； 1 小时内母体化合物完全降解，22 小时后副产物浓度保持恒定。通过超高效液相色谱-四极杆-飞行时间-串联质谱（UPLC-Q-ToF-MS/MS）对副产物的研究表明，所有三种三嗪都遵循相似的转化途径，形成四种新分子，其结构已被阐明。采用基于费氏弧菌生物发光抑制的标准方法对新产品的急性毒性进行了研究，副产物表现出比母体化合物更高的毒性。版权所有 © 2008 约翰·威利父子有限公司
• Prometryne Oxidation by Sodium Hypochlorite in Aqueous Solution: Kinetics and Mechanism
  作者：G. Mascolo、A. Lopez、R. Foldenyi、R. Passino、G. Tiravanti

  DOI：10.1021/es00012a015

  日期：1995.12.1

  The reaction of the herbicide prometryne (C9H16N5-S-CH3) with sodium hypochlorite has been investigated from the kinetic and mechanistic stand point. Under the fixed experimental conditions: pH = 7, T = 25 degrees C, [NaClO]/[substrate] = (10(-3) M)/(10(-5) M), prometryne oxidation takes place according to the following pathway: R-S-CH3 (P) --> R-SO-CH3 (a) --> R-SO2-CH3 (b) --> R-O-SO2-CH3 (x) --> R-OH (c), where R stands for C9H16N5, i.e., the substituted triazine ring of prometryne and (x) is an unexpected intermediate never previously detected nor identified. After having synthesized the pure intermediates (a), (b), and (x), the values of the pseudo-first-order kinetic constants of the first three steps were experimentally obtained: [k(1) = (0.64 +/- 0.03) s(-1), k(2) = (1.81 +/- 0.05) x 10(-3) S-1 k(3) = (1.50 +/- 0.03) x 10(-4) s(-1)]. As for k(4), its value [(2.5 +/- 0.2) x 10(-5) s(-1)] has been calculated indirectly on the basis of the kinetic theory concerning consecutive reactions. All the steps were pseudo-first-order reactions with respect to their specific substrate. The effect of pH on the hydrolysis of (b) [(b) --> (c)], in the absence of NaClO, has been also assessed to better elucidate the mechanism of the overall pathway.