5-hydroxyclomazone | 81778-16-7

• 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: 5-hydroxyclomazone
• 英文别名: 2-[(2-chlorophenyl)methyl]-5-hydroxy-4,4-dimethyl-3-isoxazolidinone；3-Isoxazolidinone, 2-[(2-chlorophenyl)methyl]-5-hydroxy-4,4-dimethyl-；2-[(2-chlorophenyl)methyl]-5-hydroxy-4,4-dimethyl-1,2-oxazolidin-3-one
• CAS: 81778-16-7
• 化学式: C₁₂H₁₄ClNO₃
• 分子量: 255.701
• InChiKey: MDZOMCCXUBFSBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异恶草酮 以 N,N-二甲基甲酰胺 为溶剂， 以3 mg的产率得到3'-hydroxyclomazone
  参考文献：
  名称：

  Microbial Transformations of Clomazone

  摘要：

  Common soil fungi and bacteria were screened for their abilities to biotransform the herbicide clomazone (2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone) into metabolites. Preparative-scale incubations were conducted with Aspergillus niger (UI-X172) and Cunninghamella echinulata (NRRL-3655) to obtain metabolites in sufficient quantities for spectral and chromatographic identification. HPLC analyses were used to assess the capacities of 41 microorganisms to metabolize the herbicide. Based on comparisons with authentic standard compounds and on the structures of metabolites ascertained by H-1 NMR and mass spectrometry, major microbial transformation reactions involved hydroxylation at the 5-methylene carbon of the isoxazolidone ring, hydroxylation of a methyl group on the oxazolidone ring, and aromatic hydroxylation at position 3'. Minor metabolic routes included dihydroxylations of clomazone on the aromatic ring, cleavage of the isoxazolidone N-C bond, or complete removal of the isoxazolidone ring to form chlorobenzyl alcohol.

  DOI：

  10.1021/jf9502663

文献信息

• Herbicidal 3-isoxazolidinones and hydroxamic acids
  申请人：FMC Corporation

  公开号：US04405357A1

  公开（公告）日：1983-09-20

  Novel 3-isoxazolidinone compounds and novel hydroxamic acid intermediates from which they are prepared exhibit herbicidal activity to grassy and broad-leaf plant species while leaving legumes, especially soybeans, unaffected. The preparation and herbicidal activity of the compounds is exemplified.

  新型3-异噁唑烷酮化合物和新型羟羧酸中间体表现出对禾本科和阔叶植物种类的除草活性，同时不影响豆科植物，特别是大豆。这些化合物的制备和除草活性得到了示范。
• US4405357A
  申请人：——

  公开号：US4405357A

  公开（公告）日：1983-09-20
• Microbial Transformations of Clomazone
  作者：Song Yu Liu、Mark Shocken、John P. N. Rosazza

  DOI：10.1021/jf9502663

  日期：1996.1.1

  Common soil fungi and bacteria were screened for their abilities to biotransform the herbicide clomazone (2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone) into metabolites. Preparative-scale incubations were conducted with Aspergillus niger (UI-X172) and Cunninghamella echinulata (NRRL-3655) to obtain metabolites in sufficient quantities for spectral and chromatographic identification. HPLC analyses were used to assess the capacities of 41 microorganisms to metabolize the herbicide. Based on comparisons with authentic standard compounds and on the structures of metabolites ascertained by H-1 NMR and mass spectrometry, major microbial transformation reactions involved hydroxylation at the 5-methylene carbon of the isoxazolidone ring, hydroxylation of a methyl group on the oxazolidone ring, and aromatic hydroxylation at position 3'. Minor metabolic routes included dihydroxylations of clomazone on the aromatic ring, cleavage of the isoxazolidone N-C bond, or complete removal of the isoxazolidone ring to form chlorobenzyl alcohol.