N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinylurea) | 138724-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinylurea)
• 英文别名: N-(2,4-dimethoxy-2-pyrimidinyl)-N-[(3-(ethylsulfonyl)-2-pyridinyl)]urea；N-(4,6-Dimethoxy-2-pyrimidinyl)-N-(3-(ethylsulfonyl)-2-pyridinyl)urea；1-(4,6-dimethoxypyrimidin-2-yl)-1-(3-ethylsulfonylpyridin-2-yl)urea
• CAS: 138724-53-5
• 化学式: C₁₄H₁₇N₅O₅S
• 分子量: 367.385
• InChiKey: YKUAHBLGZCTWPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  砜嘧磺隆 在 Al hectorite 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinylurea)
  参考文献：
  名称：

  Adsorption and Degradation of Rimsulfuron on Al Hectorite

  摘要：

  A study was carried out to examine the interactions between a smectite (hectorite) saturated with Al3+ and a sulfonylurea herbicide, rimsulfuron [N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide]. As rimsulfuron is extremely unstable in water, to evaluate the role of the clay surface in decomposing the herbicide, the experiments were carried out in chloroform solution. The coordination of the C=O group is initially involved in the adsorption as revealed by FT-IR analysis. The adsorbed rimsulfuron decomposes initially into N-(4,6 dimethoxypyrimidin-2-yl)-N-((3-(ethylsulfonyl)-2-pyridinyl)urea (metabolite 367). This metabolite is adsorbed onto a clay surface by coordination of the C=O group-and protonation of the pyrimidine ring. Successively, this metabolite decomposes on a clay surface to N-[(3-ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2-pyrimidineamine (metabolite 324). This second metabolite remains adsorbed by protonation of its pyrimidine ring.

  DOI：

  10.1021/jf950107j

文献信息

• Rouchaud, J.; Neus, O.; Moulard, C., Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 1, p. 59 - 66
  作者：Rouchaud, J.、Neus, O.、Moulard, C.

  DOI：——

  日期：——
• Soil Metabolism of the Herbicide Rimsulfuron under Laboratory and Field Conditions
  作者：Jean Rouchaud、Olivier Neus、Dany Callens、Robert Bulcke

  DOI：10.1021/jf9606161

  日期：1997.8.1

  Procedures were developed for soil analysis of rimsulfuron and its metabolites by means of GC-ECD, GC-FPD and GC-MS with a detection limit of 1 mu g of rimsulfuron equivalents per kilogram of dry soil, after purification of the soil extracts by TLC. Soil containing an exaggerated rimsulfuron concentration was incubated in the laboratory, in order to adjust the analytical procedures. To evaluate the role of different manuring managements, rimsulfuron was applied postemergence (10 g ha(-1) on a corn field in 1994 and 1995) on plots treated with (1) green manure, pig slurry applied in (2) November and (3) March, and cow manure applied in (4) November and (5) March and (6) untreated control plots without organic fertilizer. Neither rimsulfuron nor its metabolites were detected at soil depths lower than 8 cm. The results show that manure managements prolong rimsulfuron half-life in the 0-8 cm surface soil layer from a minimum of 14 days (control) to a maximum of 46 days (pig slurry in March). At corn harvest, rimsulfuron and its metabolites were not detected in soil. Similar soil degradation pathways were observed in the field as in the laboratory. N-(4,6-Dimethoxypyrimidin-2-yl)-N-[3-(ethylsulfonyl)-2-pyridinyl]urea 2 was a transient soil degradation product. N-[3-(ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2-pyrimidineamine 3 attained a maximum soil concentration after 20 days of incubation and then progressively disappeared and could not be detected after 40 days. The high-molecular weight amine 3 did not accumulate in soil, eliminating the concern for potential formation of nitroso amino compounds. 2-Hydroxy-3-(ethylsulfonyl)pyridine 4 became the major rimsulfuron soil degradation product. The soil concentrations increased and attained a maximum after 40 days of incubation and then decreased; its isomerization into 2-pyridone, followed by hydrolysis, could transform it into low molecular weight nontoxic products. The concentrations of 2-amino-4,6-dimethoxypyrimidine 5 were somewhat lower than those of compound 4.
• Adsorption and Degradation of Rimsulfuron on Al Hectorite
  作者：Ottorino Pantani、Alba Pusino、Luca Calamai、Carlo Gessa、Paolo Fusi

  DOI：10.1021/jf950107j

  日期：1996.1.1

  A study was carried out to examine the interactions between a smectite (hectorite) saturated with Al3+ and a sulfonylurea herbicide, rimsulfuron [N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide]. As rimsulfuron is extremely unstable in water, to evaluate the role of the clay surface in decomposing the herbicide, the experiments were carried out in chloroform solution. The coordination of the C=O group is initially involved in the adsorption as revealed by FT-IR analysis. The adsorbed rimsulfuron decomposes initially into N-(4,6 dimethoxypyrimidin-2-yl)-N-((3-(ethylsulfonyl)-2-pyridinyl)urea (metabolite 367). This metabolite is adsorbed onto a clay surface by coordination of the C=O group-and protonation of the pyrimidine ring. Successively, this metabolite decomposes on a clay surface to N-[(3-ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2-pyrimidineamine (metabolite 324). This second metabolite remains adsorbed by protonation of its pyrimidine ring.