3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione | 24261-46-9

• 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: 3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione
• 英文别名: 3-(3,5-dichlorophenyl)-5-methyloxazolidine-2,4-dione；3-(3,5-dichloro-phenyl)-5-methyl-oxazolidine-2,4-dione；3-(3,5-dichloro-phenyl)-5-methyl-2,4(3H,5H)-oxazolidinedione；3-(3,5-dichlorophenyl)-5-methyl-oxazolidine-2,4-dione；3-(3,5-Dichlorophenyl)-5-methyl-1,3-oxazolidine-2,4-dione
• CAS: 24261-46-9
• 化学式: C₁₀H₇Cl₂NO₃
• 分子量: 260.076
• InChiKey: OEBOZCABBNTGJW-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±52.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione 在 水 作用下， 以 various solvent(s) 为溶剂， 生成 3,5-Dichlorophenyl-2-hydroxypropionanilide
  参考文献：
  名称：

  Mechanisms of dicarboximide ring opening in aqueous media: Procymidone, vinclozolin and chlozolinate

  摘要：

  AbstractThe hydrolysis kinetics of the dicarboximide fungicides procymidone, vinclozolin and chlozolinate in neutral and alkaline solutions of pH 60 to 13·7 at 25°C have been determined conjointly by ultraviolet spectrophotometry and by high performance liquid chromatography. Under alkaline conditions, the fungicides undergo attack by the hydroxide ion on a specific carbonyl group and the rate of hydrolysis increases proportionally to the hydroxide ion concentration. Procymidone gives quantitatively and irreversibly 2‐(3,5‐dichlorophenylcarba‐moyl)‐l,2‐dimethylcyclopropanecarboxylate. The reaction is not subject to general base catalysis and experimental data are in agreement with a rate‐determining attack by the hydroxide ion. After a rapid hydrolytic loss of the ethoxycarbonyl substituent from chlozolinate, the dicarboximide ring cleavage of the two other fungicides leads, by mechanisms which differ with respect to the type of base catalysis and the rate‐determining step, to the corresponding anilides, producing as intermediates the carbamic acids, which undergo loss of carbon dioxide. The hydrolysis of vinclozolin and chlozolinate yields, respectively, N‐(3,5‐dichloro‐phenyt)‐2‐hydroxy‐2‐methylbut‐3‐enanilide and N‐(3,5‐dichlorophenyl)‐2‐hydroxy‐propanilide.

  DOI：

  10.1002/ps.2780410206
• 作为产物：
  描述：

  乙烯菌核利 以 甲醇 、 水 为溶剂， 反应 0.17h， 生成 3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione
  参考文献：
  名称：

  Photochemistry of vinclozolin in water and methanol-water solution

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199911)55:11<1116::aid-ps65>3.0.co;2-y

文献信息

• 3-Phenyl-oxazolidine-2,4-dione microbicides
  申请人：Ciba-Geigy Corporation

  公开号：US04150144A1

  公开（公告）日：1979-04-17

  3-Phenyl-oxazolidine-2,4-dione derivatives can be halogenated directly, without splitting of the heterocyclic ring. The products thus obtained have a fungicidal action which is substantially wider than that of compounds hitherto known.

  3-苯基噁唑啉-2,4-二酮衍生物可以直接卤代，而不需要分解杂环。因此获得的产物具有广谱的杀真菌作用，比迄今为止已知的化合物范围更广。
• Kinetics and mechanisms of hydrolysis of dicarboximide fungicides in micellar media
  作者：Jean C. Villedieu、Alain de Savignac、Jean P. Calmon

  DOI：10.1021/jf00055a035

  日期：1995.7

  The kinetics of alkaline hydrolysis of the dicarboximide fungicides procymidone, iprodione, vinclozolin, and chlozolinate (1-4, respectively) were investigated in micellar solutions containing various amounts of either sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), or three nonionic surfactants (two C-13 alcohols and a copra amine combined with ethoxyl chains) and compared with the kinetics in aqueous media. For all compounds, the rate constants observed are slightly reduced by the SDS micellar media, showing that reactions essentially take place in the aqueous pseudophase. The CTAB micellar media speed up the hydrolysis rates with small quantities of Br- ions in the medium. As the number of Br- ions increases, the rate of reactions falls. This is characteristic of an ion exchange (OH- and Br-) at the surface of the CTAB micelles. Finally, the presence of nonionic micelles has little influence on the hydrolysis of the fungicides: the reduction in the rate of dicarboximide ring opening is attributed to micelle-substrate association. These results can be explained by means of the pseudophase kinetic model coupled with the mechanisms of hydrolysis of these fungicides in water solution.
• Fungicidal N-phenylcarbamates
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0104070B1

  公开（公告）日：1986-12-30
• US4150144A
  申请人：——

  公开号：US4150144A

  公开（公告）日：1979-04-17
• Photochemistry of vinclozolin in water and methanol-water solution
  作者：Bernhard Schick、Pran N Moza、Klaus Hustert、Antonius Kettrup

  DOI：10.1002/(sici)1096-9063(199911)55:11<1116::aid-ps65>3.0.co;2-y

  日期：1999.11