3-(2,6-dimethylphenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | 1639426-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(2,6-dimethylphenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
• 英文别名: benquitrione；3-(2,6-dimethylphenyl)-6-{(2-hydroxy-6-oxo-1-cyclohexene-1-yl)carbonyl}-1-methyl-2,4(1H,3H)quinazolinedione；kuicaotong
• CAS: 1639426-14-4
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: IFHRYUOSJUERAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  627.9±65.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.37
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-硝基异邻苯二甲酸二甲酯 在 吡啶 、 氯化亚砜 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 丙酮氰醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2,6-dimethylphenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Herbicidal Evaluation of Triketone-Containing Quinazoline-2,4-diones

  摘要：

  Exploring novel 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) inhibitors is one of the most promising research directions in herbicide discovery. To discover new triketone herbicides with broad-spectrum weed control as well as excellent crop selectivity, a series of (total 52) novel triketone-containing quinazoline-2,4-dione derivatives were synthesized and further bioevaluated. The greenhouse testing indicated that many of the newly synthesized compounds showed better or excellent herbicidal activity against broadleaf and monocotyledonous weeds at the dosages of 37.5150 g of active ingredient (ai)/ha. The structure and activity relationship in this study indicated that the triketone-containing quinazoline-2,4-dione motif has possessed great impact on herbicide activity and may be used for further optimization. Among the new compounds, III-b and VI-aVI-d displayed a broader spectrum of weed control than mesotrione. In addition, the compound III-b also demonstrated comparatively superior crop selectivity to mesotrione, thus possessing great potential for weed control in the field.

  DOI：

  10.1021/jf5048089

文献信息

• TRIKETONE COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF, AND HERBICIDE
  申请人：Shandong Cynda Chemical Co., LTD.

  公开号：EP3858818A1

  公开（公告）日：2021-08-04

  A triketone compound, a preparation method therefor and the use thereof, and a herbicide are disclosed. The compound has a structure represented by formula (I). The triketone compound can be used as an HPPD herbicide for controlling gramineous weeds and broadleaf weeds. The triketone compound has good control effects on various gramineous weeds and some broadleaf weeds which are harmful to wheat and/or peanut growth.

  本发明公开了一种三酮化合物、其制备方法和用途以及一种除草剂。该化合物具有由式（I）表示的结构。三酮化合物可用作 HPPD 除草剂，用于控制禾本科杂草和阔叶杂草。三酮化合物对各种禾本科杂草和一些对小麦和/或花生生长有害的阔叶杂草具有良好的防除效果。
• Synthesis and Herbicidal Evaluation of Triketone-Containing Quinazoline-2,4-diones
  作者：Da-Wei Wang、Hong-Yan Lin、Run-Jie Cao、Sheng-Gang Yang、Qiong Chen、Ge-Fei Hao、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1021/jf5048089

  日期：2014.12.10

  Exploring novel 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) inhibitors is one of the most promising research directions in herbicide discovery. To discover new triketone herbicides with broad-spectrum weed control as well as excellent crop selectivity, a series of (total 52) novel triketone-containing quinazoline-2,4-dione derivatives were synthesized and further bioevaluated. The greenhouse testing indicated that many of the newly synthesized compounds showed better or excellent herbicidal activity against broadleaf and monocotyledonous weeds at the dosages of 37.5150 g of active ingredient (ai)/ha. The structure and activity relationship in this study indicated that the triketone-containing quinazoline-2,4-dione motif has possessed great impact on herbicide activity and may be used for further optimization. Among the new compounds, III-b and VI-aVI-d displayed a broader spectrum of weed control than mesotrione. In addition, the compound III-b also demonstrated comparatively superior crop selectivity to mesotrione, thus possessing great potential for weed control in the field.