methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate
• 英文别名: Methyl 2-(acetylcarbamoylcarbamoylcarbamoylsulfamoyl)benzoate；methyl 2-(acetylcarbamoylcarbamoylcarbamoylsulfamoyl)benzoate
• 化学式: C₁₃H₁₄N₄O₈S
• 分子量: 386.342
• InChiKey: UIRDQZNZSRGAQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  acetylbiuret 、 2-异氰酸磺酰基苯甲酸甲酯 以 xylene 为溶剂， 反应 5.0h， 以47%的产率得到methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate
  参考文献：
  名称：

  Aerobic soil metabolism of metsulfuron-methyl

  摘要：

  A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20 degrees C. Bath [phenyl-U-C-14]- and [triazine-2-C-14]metsulfuron-methyl were used. The soil was treated with [C-14]metsulfuron-methyl (0.1 mg kg(-1)) and incubated in flow-through systems for one year. The degradation rate constants, DT50, and DT90 were obtained based on the first-order and biphasic models. The DT50 (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9-11 days, 95% confidence limits) in the non-sterile soil and 20 days (12-32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-C-14] and [triazine-2-C-14]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[ [ [ [ [ [ [(acetylamino)carbonyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[ [ [ [ [amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. (C) 1999 Society of Chemical Industry.

  DOI：

  10.1002/(sici)1096-9063(199904)55:4<434::aid-ps909>3.0.co;2-z

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。
• Aerobic soil metabolism of metsulfuron-methyl
  作者：Yutai Li、W T Zimmerman、M K Gorman、R W Reiser、A J Fogiel、P E Haney

  DOI：10.1002/(sici)1096-9063(199904)55:4<434::aid-ps909>3.0.co;2-z

  日期：1999.4

  A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20 degrees C. Bath [phenyl-U-C-14]- and [triazine-2-C-14]metsulfuron-methyl were used. The soil was treated with [C-14]metsulfuron-methyl (0.1 mg kg(-1)) and incubated in flow-through systems for one year. The degradation rate constants, DT50, and DT90 were obtained based on the first-order and biphasic models. The DT50 (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9-11 days, 95% confidence limits) in the non-sterile soil and 20 days (12-32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-C-14] and [triazine-2-C-14]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[ [ [ [ [ [ [(acetylamino)carbonyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[ [ [ [ [amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. (C) 1999 Society of Chemical Industry.