sec-butyl-imidazolidinetrione | 40408-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: sec-butyl-imidazolidinetrione
• 英文别名: 1-Butan-2-ylimidazolidine-2,4,5-trione
• CAS: 40408-59-1
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: HEVQRKNYQRPXPR-UHFFFAOYSA-N

物化性质

• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  西玛嗪 在 臭氧 作用下， 以24%的产率得到5-acetyl-3-sec-butyl-5-hydroxy-imidazolidine-2,4-dione
  参考文献：
  名称：

  Kinetics of Bromacil Ozonolysis

  摘要：

  Chemical oxidation processes have been used successfully in the degradation of organic pollutants, yet information is limited concerning the kinetic descriptions of the reaction mechanisms. In this study, the kinetics of bromacil (5-bromo-3-sec-butyl-6-methyluracil, a herbicide) ozonolysis was examined. From laboratory observations, a mechanism was proposed by which direct ozone attack occurred and the degradation pathway proceeded via two parallel reactions. The program MLAB was used to provide a numerical solution for the system of differential equations that described the mechanism. Rate parameters were determined using the slowest reaction system (H2O2/O-3). The kinetic model was then tested on a system with only bromacil and on a system containing a radical scavenger. This mathematical model is reasonably consistent with the experimental observations that the addition of hydrogen peroxide significantly reduces the formation of the byproduct responsible for the residual phytotoxicity of the waste stream.

  DOI：

  10.1021/jf970651n

文献信息

• Mechanistic Investigations Concerning the Aqueous Ozonolysis of Bromacil
  作者：Cathleen J. Hapeman、Brent G. Anderson、Alba Torrents、Aurel J. Acher

  DOI：10.1021/jf9600420

  日期：1997.3.1

  Bromacil ozonolysis was examined to determine the mechanism of product formation in an effort to optimize a chemical-microbial remediation strategy for contaminated waters. Two debrominated products, 3-sec-butyl-5-acetyl-5-hydroxyhydantoin (II) (24%) and 3-sec-butylparabanic acid (III) (56%), and a dibromohydrin, 3-sec-butyl-5,5-dibromo-6-methyl-6-hydro (IV) (20%), were formed. The latter compound, arising from HOBr addition to bromacil, reverted back to starting material, causing the treated solution to remain somewhat phytotoxic. Mass balance studies provided evidence for parallel reaction pathways as opposed to a series pathway where II gives rise to III. Addition of hydrogen peroxide slightly decreased the rate of bromacil degradation while the addition of tert-butyl alcohol (t-BuOH), a hydroxy radical scavenger, increased the degradation rate, strongly suggesting that the mechanism does not involve hydroxy radicals but direct ozone attack at the double bond. A much lower yield of IV, 6%, relative to the control was observed with H2O2, whereas a slightly higher yield, 23%, was found with t-BuOH.
• Comparison of Formation and Biodegradation of Bromacil Oxidation Products in Aqueous Solutions
  作者：Aurel J. Acher、Cathleen J. Hapeman、Daniel R. Shelton、Mark T. Muldoon、William R. Lusby、Adi Avni、Rolland Waters

  DOI：10.1021/jf00045a039

  日期：1994.9

  A comparative study of several oxidation methods of aqueous bromacil (I) solutions was conducted as part of a series of investigations concerning the chemical and biological remediation of pesticide-laden wastes. Ozonation (A), UV photolysis at 254 nn (B), and sensitized sunlight photodegradation (C) methods were examined. The A products were isolated and their structures elucidated by mass spectroscopy, various C-13 and H-1 NMR techniques, and other chemical methods. Three main A products were identified: 3-sec-butyl-5-acetyl-5-hydroxyhydantoin (II, ca. 5%), 3-sec-butylparabanic acid (III, ca. 20%), and 3-sec-butyl-5,5-dibromo-6-methyl-6-hydroxyuracil (IV, ca. 5%), which was also synthesized via hydroxybromination of bromacil; a fourth product (VII) was obtained in minute amount but was not identified. The aqueous solutions of IV are unstable and its decomposition led to re-formation of I. The main products found in B [(3-sec-butyl-6-methyluracil (V) and a dimer compound, VI] and C (II and VI) were similar to those described previously. The biodegradation assays of I, A, B, and C solutions were investigated using activated sludge, a pure culture of Klebsiella terragena (DRS-I), or soil; they indicated that the B and C solutions were more biodegradable than A solutions, while the parent material (I) was nonbiodegradable. A phytotoxicity bioassay, using Nicotiana tabacum seedlings, showed complete detoxification of the B and C solutions but only partial detoxification of the A and IV solutions. An attempt has been made to evaluate the most suitable method of degradation of solutions of I.