bromoxynil sodium | 2961-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bromoxynil sodium
• 英文别名: bromoxynil；3,5-dibromo-4-hydroxybenzonitrile sodium salt；Sodium 3,5-dibromo-4-hydroxyphenylcyanide；sodium;2,6-dibromo-4-cyanophenolate
• CAS: 2961-67-3
• 化学式: C₇H₂Br₂NO*Na
• 分子量: 298.897
• InChiKey: AMWJYRKCJBFTAZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bromoxynil sodium 、 四丁基溴化铵 以 甲醇 为溶剂， 以96%的产率得到tetrabutylammonium 2,6-dibromo-4-cyanophenolate
  参考文献：
  名称：

  基于溴苯腈的离子液体，可减少对环境和人类健康的不利影响†

  摘要：

  许多除草剂在施用后均表现出一些缺点，例如高水溶性和挥发性，这会导致对水生和大气环境以及人类健康的潜在威胁。通过与适当的抗衡离子（阳离子或阴离子）配对，除草离子液体（HIL）可以有效消除这些固有的缺点。在这项研究中，合成了基于具有八种典型阳离子的溴苯腈的新HIL，以减少当前使用的溴苯腈形式的负面影响。研究了所有获得的化合物在温室中的溶解度，辛醇-水分配系数，表面活性，挥发速率和除草活性。结果表明，阳离子中具有长烷基链的HIL具有降低的水溶性和挥发速率，具有更好的表面活性和ķ流，并且防止过溴苯腈钠杂草基本上改善的功效。由于HIL具有可调节的理化特性和改善的除草活性，因此它们可以极大地减少溴苯腈对环境和人类健康的不利影响，并且在将来可能成为目前流行的溴苯腈替代品的潜在替代品。

  DOI：

  10.1039/c7nj01694h
• 作为产物：
  描述：

  4-羟基苯甲腈 在 盐酸 、 sodium bromate 、 sodium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 bromoxynil sodium
  参考文献：
  名称：

  Synthesis and Evaluation of Heterocyclic Analogues of Bromoxynil

  摘要：

  One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee-Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory ( Ipomoea lacunose ) when applied at 0.28 kg ha(-1). A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha(-1). Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.

  DOI：

  10.1021/jf404209d