(3-氧代-1,4-苯并恶嗪-4-基)丁酸酯 | 918639-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: (3-氧代-1,4-苯并恶嗪-4-基)丁酸酯
• 英文名称: 4-butanoyloxy-(2H)-1,4-benzoxazin-3(4H)-one
• 英文别名: Bu-D-DIBOA；4-(Butanoyloxy)-2H-1,4-benzoxazin-3(4H)-one；(3-oxo-1,4-benzoxazin-4-yl) butanoate
• CAS: 918639-47-1
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: HUSUJNYKXOEVFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.1±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁酰氯 、 4-羟基-2H-1,4-苯并噁嗪-3(4h)-酮 在 吡啶 作用下， 反应 12.0h， 以99%的产率得到(3-氧代-1,4-苯并恶嗪-4-基)丁酸酯
  参考文献：
  名称：

  Modified Benzoxazinones in the System Oryza sativa−Echinochloa crus-galli: An Approach to the Development of Biorational Herbicide Models

  摘要：

  The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been explored. The work described focuses on obtaining derivatives that present selectivity in the system Oryza sativa-Echinochloa crus-galli. To achieve this goal the influence of lipophilicity in this system has been studied by preparing 14 ester derivatives at the N-4 position of D-DIBOA along with other compounds with different functionalization and chain lengths at position C-2. These compounds have been tested in the aforementioned system, and the dose-response profiles have been compared. The most active compound was 2-ethyl-4-hydroxy(2H)-1,4-benzoxazin-3(4H)-one, which presented higher selectivity than the specific herbicide Cotanil-35. These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops.

  DOI：

  10.1021/jf802735m

文献信息

• Optimization of Benzoxazinones as Natural Herbicide Models by Lipophilicity Enhancement
  作者：Francisco A. Macías、David Marín、Alberto Oliveros-Bastidas、José M. G. Molinillo

  DOI：10.1021/jf062168v

  日期：2006.12.1

  Benzoxazinones are plant allelochemicals well-known for their phytotoxic activity and for taking part in the defense strategies of Gramineae, Ranunculaceae, and Scrophulariceae plants. These properties, in addition to the recently optimized methodologies for their large-scale isolation and synthesis, have made some derivatives of natural products, 2,4-dihydroxy-(2H)-1,4-benzoxazin-3-(4H)-one (DIBOA) and its 7-methoxy analogue ( DIMBOA), successful templates in the search for natural herbicide models. These new chemicals should be part of integrated methodologies for weed control. In ongoing research about the structure-activity relationships of benzoxazinones and the structural requirements for their phytotoxicity enhancement and after characterization of the optimal structural features, a new generation of chemicals with enhanced lipophilicity was developed. They were tested on selected standard target species and weeds in the search for the optimal aqueous solubility-lipophilicity rate for phytotoxicity. This physical parameter is known to be crucial in modern drug and agrochemical design strategies. The new compounds obtained in this way had interesting phytotoxicity profiles, empowering the phytotoxic effect of the starting benzoxazinone template in some cases. Quantitative structure-activity relationships were obtained by bioactivity-molecular parameters correlations. Because optimal lipophilicity values for phytotoxicity vary with the tested plant, these new derivatives constitute a more selective way to take advantage of benzoxazinone phytotoxic capabilities.
• Modified Benzoxazinones in the System <i>Oryza sativa</i>−<i>Echinochloa crus-galli</i>: An Approach to the Development of Biorational Herbicide Models
  作者：Francisco A. Macías、Nuria Chinchilla、Rosa M. Varela、José M. G. Molinillo、David Marín、João M. De Siqueira

  DOI：10.1021/jf802735m

  日期：2008.11.12

  The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been explored. The work described focuses on obtaining derivatives that present selectivity in the system Oryza sativa-Echinochloa crus-galli. To achieve this goal the influence of lipophilicity in this system has been studied by preparing 14 ester derivatives at the N-4 position of D-DIBOA along with other compounds with different functionalization and chain lengths at position C-2. These compounds have been tested in the aforementioned system, and the dose-response profiles have been compared. The most active compound was 2-ethyl-4-hydroxy(2H)-1,4-benzoxazin-3(4H)-one, which presented higher selectivity than the specific herbicide Cotanil-35. These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops.