methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate | 126312-31-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate
• 英文别名: methyl 2-[[[(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonylamino]sulfonyl]benzoate；methyl 2-(N-((4-hydroxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl)sulfamoyl)benzoate；O-desmethyl metsulfuron-methyl；Desmethyl Metsulfuron-methyl；methyl 2-[(2-methyl-6-oxo-1H-1,3,5-triazin-4-yl)carbamoylsulfamoyl]benzoate
• CAS: 126312-31-0
• 化学式: C₁₃H₁₃N₅O₆S
• 分子量: 367.342
• InChiKey: XCRRTPZSEWGCGA-UHFFFAOYSA-N

物化性质

• 熔点：
  >70°C (dec)
• 溶解度：
  DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲磺隆 生成 methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate
  参考文献：
  名称：

  Transformation rates ofortho-substituted thiophene and benzene carboxylic esters: Application to thifensulfuron-methyl and metsulfuron-methyl herbicides

  摘要：

  AbstractThe rate constants for soil degradation and alkaline hydrolysis of two herbicides, metsulfuron‐methyl and thifensulfuron‐methyl, have been determined. In order to explain the difference in behaviour of the two compounds, the chemical and enzymatic hydrolysis of some ortho‐substituted methyl benzoates and methyl 3‐substituted thiophene‐2‐carboxylates were studied. The data are consistent with a difference in polar and steric effects of the substituents in benzene and thiophene derivatives.

  DOI：

  10.1002/ps.2780400407

文献信息

• Application of liquid chromatography/electrospray ionization tandem mass spectrometry for the elucidation of hydroxyl radical oxidation of metsulfuron methyl and related sulfonylurea pesticide products: evidence for the triazine skeleton scission
  作者：Rajae Chahboune、Hafida Mountacer、Mohamed Sarakha

  DOI：10.1002/rcm.7234

  日期：2015.8.15

  by excitation of the iron(III) aquacomplex [Fe(H(2)O)OH](2+) and hydrogen peroxide at pH 3.5. Three different sulfonylureas were studied: metsulfuron methyl, cinosulfuron and thifensulfuron methyl. RESULTS Several products owing to the reactivity of hydroxyl radicals with sulfonylurea were obtained. They arise from scission of the sulfonylurea bridge, hydroxylation of the aromatic ring, demethylation

  理由磺脲类药物是最重要的一类抗糖尿病药和除草剂。由于结构相对复杂，太阳光激发和高级氧化过程可能导致形成各种各样的产物。这些应该被鉴定的产品可能比母体化合物具有更大的毒性作用。方法液相色谱/电喷雾电离四极杆飞行时间质谱（LC / ESI-QTOFMS）具有精确的质量测定方法，是一种精确阐明所有可能副产物的有价值的技术。通过在pH 3.5下激发铁（III）水络合物[Fe（H（2）O）OH]（2+）和过氧化氢产生羟基自由基。研究了三种不同的磺酰脲类：甲磺隆，辛磺隆和噻吩磺隆。结果由于羟基与磺酰脲的反应性，得到了几种产物。它们起因于磺酰脲桥的断裂，芳环的羟基化，甲氧基的去甲基化，以及更重要的和明确的三嗪骨架的断裂。为了达成这种分裂，三嗪部分上的甲氧基的伯基去甲基化似乎充当了前体过程。用三种研究过的磺酰脲类化合物观察到了这一过程。结论所报告的结果证明了LC / ESI-QTOFMS进行精确质量测量对
• Study of the Hydrolysis of a Sulfonylurea Herbicide Using Liquid Chromatography with Diode Array Detection and Mass Spectrometry by Three-Way Multivariate Curve Resolution−Alternating Least Squares
  作者：Ernst Bezemer、Sarah Rutan

  DOI：10.1021/ac0101656

  日期：2001.9.1

  different pHs and temperatures by reversed-phase liquid chromatography using a diode array detector. The data are analyzed using a three-way, multivariate curve resolution technique. Of special interest was the application of a closure constraint in the kinetic dimension followed by the determination of the rate constants for each step of the pathway by using a differential equation solver and nonlinear fitting

  这项研究的重点是开发一种新颖的自动化学计量方法，该方法可从不断发展的化学系统的时程测量中获取相关的化学信息。本文介绍了磺酰脲类除草剂Ally水解的研究。使用二极管阵列检测器通过反相液相色谱在不同的pH和温度下观察到该化合物的水解。使用三向多元曲线分辨率技术分析数据。特别感兴趣的是在动力学尺寸中应用闭合约束，然后使用微分方程求解器和数据的非线性拟合确定路径每一步的速率常数。
• Transformation rates of<i>ortho</i>-substituted thiophene and benzene carboxylic esters: Application to thifensulfuron-methyl and metsulfuron-methyl herbicides
  作者：Jean Bastide、Robert Badon、Jean-Pierre Cambon、Danielle Vega

  DOI：10.1002/ps.2780400407

  日期：1994.4

  AbstractThe rate constants for soil degradation and alkaline hydrolysis of two herbicides, metsulfuron‐methyl and thifensulfuron‐methyl, have been determined. In order to explain the difference in behaviour of the two compounds, the chemical and enzymatic hydrolysis of some ortho‐substituted methyl benzoates and methyl 3‐substituted thiophene‐2‐carboxylates were studied. The data are consistent with a difference in polar and steric effects of the substituents in benzene and thiophene derivatives.
• Kinetics and hydrolysis mechanism of chlorsulfuron and metsulfuron-methyl
  作者：Saadi Hemmamda、Michelle Calmon、Jean P. Calmon

  DOI：10.1002/ps.2780400112

  日期：1994.1

  AbstractIn acidic media, hydrolysis of chlorsulfuron and metsulfuron‐methyl occurs via two consecutive reactions which were followed by ultraviolet spectrophotometry. For these two reactions, the pseudo‐first‐order rate constants increase proportionally to the concentration of hydronium ion in the more acidic media and to the square of this concentration at higher pH values.A kinetic study by HPLC shows that the first reaction leads to the formation of 4‐methoxy‐6‐methyl‐1,3,5‐triazin‐2‐amine and (o‐chlorophenylsulfonyl) carbamic acid for chlorsulfuron or (o‐methoxycarbonylphenylsulfonyl) carbamic acid for metsulfuronmethyl. The second reaction is the conversion of these sulfonylcarbamic acids to sulfonamides and carbon dioxide. The complete lack of saccharin and of o‐sulfamoyl benzoic acid proves that the ester function of the methoxycarbonyl group is stable.The lack of general acid‐base catalysis and a solvent deuterium isotope effect less than unity are consistent with a rate‐determining cleavage of the protonated substrate.In the basic pH range (10–14) a single reaction occurs, the nucleophilic substitution of the methoxy group on the triazine by a hydroxide group.
• EXPRESSION OF HERBICIDE METABOLIZING CYTOCHROMES P450
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0554240B1

  公开（公告）日：1996-01-17