pyriminobac-methyl | 136191-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyriminobac-methyl
• 英文别名: methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-(N-hydroxy-C-methylcarbonimidoyl)benzoate
• CAS: 136191-63-4
• 化学式: C₁₆H₁₇N₃O₆
• 分子量: 347.327
• InChiKey: UPGZGCNYHRVTJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  pyriminobac-methyl 以 甲醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Studies of the New Herbicide KIH-6127. 4. Crystal Structure of KIH-6127 and Quantitative Structure−Activity Relationship of the Iminoxy Moiety of KIH-6127 Derivatives

  摘要：

  The crystal structure of the major isomer of KIH-6127 was investigated by X-ray crystallographic techniques. The solid state structure and its conformation were confirmed as the E form. Thus KIH-6127 is mainly consistent with methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-E-(methoxy-imino)ethyl] benzoate (compound 1: Table 1). Further modifications of the iminoxy moiety to introduce a variety of haloalkyl, haloalkenyl, and others were made, and the Z isomers of several derivatives were prepared. The physicochemical properties of these derivatives were measured, including their log P and K-d values. We tested their herbicidal activity against barnyard grass and their phytotoxicity to transplanted rice in flooded paddy conditions. We also studied the role of the iminoxy moiety, on the basis of the hypothesis that the difference in the E/Z configurations of the iminoxy moiety determines their biological activity. However, clear differences in the herbicidal activities were not observed between these isomer groups. Each Z isomer was more hydrophilic than its E counterpart. To investigate this finding more intensively in a single E/Z pair, the surface area of each E/Z isomer of KIH-6127 was calculated from the X-ray data for the KIH-6127 E form. The Z conformation of the iminoxy moiety appears to take a more compact molecular conformation, resulting in the Z isomer having more hydrophilic surface area than the corresponding E isomer. QSAR studies focused on the iminoxy moiety. Both pre- and post-emergence activities of the compounds were well correlated with the square of the log P value for both configurations of the iminoxy moiety. In other words, these configurations merely contributed to the activity by way of their hydrophilicity. The difference between optimum log P values for pre- versus post-emergence indicated that the optimum compound is more lipophilic for pre- than for post-emergence activity. Phytotoxity against rice also correlated well with the K-d value. Thus stronger soil adsorption of the compounds provides higher safety for rice. On the basis of those QSAR studies, compound I was selected as the optimal compound for development as a commercial herbicide.

  DOI：

  10.1021/jf960844v
• 作为产物：
  描述：

  Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate 在 盐酸羟胺 、 potassium acetate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 pyriminobac-methyl
  参考文献：
  名称：

  Studies of the New Herbicide KIH-6127. Part III. Synthesis and Structure-Activity Studies of Analogues of KIH-6127 against Barnyard Grass (Echinochloa oryzicola)*

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199701)49:1<76::aid-ps491>3.0.co;2-e