1-(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea | 183889-68-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea
• 英文别名: 1-(2-Methyl-6-oxo-1H-1,3,5-triazin-4-yl)-3-[2-(3,3,3-trifluoropropyl)phenyl]sulfonylurea
• CAS: 183889-68-1
• 化学式: C₁₄H₁₄F₃N₅O₄S
• 分子量: 405.357
• InChiKey: IRTSSKZJZPPPHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氟磺隆 在 1,8-萘二甲酸酐 、 乙醇 、 增效醚 、 氧气 、 还原型辅酶II(NADPH)四钠盐 、 cytochrome P₄₅₀ 作用下， 反应 1.0h， 生成 、 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)-5-hydroxyphenylsulfonyl]urea 、 1-(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea 、 1-[4-(hydroxymethyl)-6-methoxy-1,3,5-triazin-2-yl]-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea
  参考文献：
  名称：

  Cytochrome P450-Dependent Hydroxylation of Prosulfuron (CGA 152005) by Wheat Seedling Microsomes

  摘要：

  Microsomes isolated from shoot tissues of etiolated wheat seedlings (Triticum aestivum L. var. Olaf) oxidized the sulfonylurea herbicide prosulfuron (CGA 152005). One major and two minor enzymatic oxidation products were isolated and identified by negative ion FAB/MS and cochromatography (TLC and HPLC) with reference standards. Identification of the major oxidation product (I) as 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl]-3-[2-(3,3,3-trifluoropropyl)-5-hydroxyphenylsulfonyl]urea was confirmed by proton NMR spectroscopy. Minor oxidation products were tentatively identified as 1-[4-(hydroxymethyl)-6-methoxy-1,3,5-triazin-2-yl]-3-[2-(3,3,3-trifluoropropyl)phenyl-sulfonyl]urea (II) and an intermediate oxidation product 1-[4-[(hydroxymethyl)oxy]-6-methyl]-1,3,5-triazin-2-yl]-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea (III) that degraded to 1-(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea (IV). Microsomal oxidation of prosulfuron required NADPH and molecular oxygen. Constitutive enzyme activity was increased 5-28-fold by induction with ethanol and with the herbicide safeners naphthalic anhydride or cloquintocet-mexyl (CGA 185072) and by combinations of naphthalic anhydride or cloquintocet-mexyl with ethanol. Inhibition of enzyme activity by CO in the dark was reversible by light. Other inhibitors of prosulfuron oxidation included tetcyclacis, piperonyl butoxide, cytochrome c, polyclonal antibodies raised against wheat cytochrome c (P450) reductase, and the herbicides bifenox and linuron. Kinetic studies established that the apparent K-m for prosulfuron was 12.6 +/- 1.1 mu M and that bifenox and linuron were noncompetitive and mixed-type inhibitors of prosulfuron oxidation,respectively, with apparent K-i values of 210 and 59 mu M.

  DOI：

  10.1021/jf960186e

文献信息

• Microbial Transformations of Prosulfuron
  作者：Kerry Kulowski、Eric L. Zirbes、Bruce M. Thede、John P. N. Rosazza

  DOI：10.1021/jf9604495

  日期：1997.4.1

  Microbial transformations were conducted with prosulfuron 1-(4'-methoxy-6'-methyltriazin-2'-yl)-3-[[2 ''-(3''',3''',3''' -trifluoropropyl)phenyl]sulfonyl]urea} to identify pathways by which the sulfonylurea herbicide is metabolized by microorganisms. Streptomyces griseolus produced four new hydroxylated metabolites which were isolated, chromatographically purified, and characterized by mass spectrometry and NMR spectroscopy as the following: a benzyl alcohol from methyl hydroxylation on the triazine ring, phenolic and catechol metabolites by 3 '' and subsequent 4 '' hydroxylation on the carbocyclic aromatic ring, and a second benzylic alcohol obtained by microbial hydroxylation of the trifluoropropyl side chain. The new metabolites were used as analytical standards for soil incubation studies.