1,3-二硝基-吩嗪 | 13860-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 1,3-二硝基-吩嗪
• 英文名称: 1,3-dinitrophenazine
• 英文别名: 1,3-Dinitro-phenazin
• CAS: 13860-47-4
• 化学式: C₁₂H₆N₄O₄
• 分子量: 270.204
• InChiKey: YHMYIFUNFCEUIM-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C (decomp)
• 沸点：
  497.9±20.0 °C(Predicted)
• 密度：
  1.610±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-二硝基-吩嗪 在 硫化氢 、 氨 作用下， 生成 1,3-二硝基-5,10-二氢吩嗪
  参考文献：
  名称：

  Kehrmann; Havas, Chemische Berichte, 1913, vol. 46, p. 346

  摘要：

  DOI：
• 作为产物：
  描述：

  酚嗪 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1,3-二硝基-吩嗪
  参考文献：
  名称：

  Kehrmann; Havas, Chemische Berichte, 1913, vol. 46, p. 346

  摘要：

  DOI：

文献信息

• Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite
  作者：Stefany Castaldi、Marco Masi、Francisco Sautua、Alessio Cimmino、Rachele Isticato、Marcelo Carmona、Angela Tuzi、Antonio Evidente

  DOI：10.3390/biom11111728

  日期：——

  Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydroxyphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α- or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications.

  Pseudomonas fluorescens 9和Bacillus subtilis 54被提议作为生物杀菌剂，用于控制大豆和其他作物的危险病原体Macrophomina phaseolina。为了评估它们产生具有抗真菌活性的代谢物的能力，在体外培养了这些细菌。本文的目的是确定其抗真菌活性的自然化合物。只有P. fluorescens 9的培养滤液显示出对M. phaseolina的强烈抗真菌活性。其有机提取物含有苯肼和丙酮酸（1和2），对M. phaseolina、Cercospora nicotianae和Colletotrichum truncatum等大豆病原体的抗真菌活性进行了测试，但只有化合物1表现出活性。将化合物1的抗真菌活性与苯肼-1-羧酸（PCA，3）、2-羟基苯肼（2-OH P，4）以及各种半合成苯肼硝基衍生物进行比较，以进行结构-活性关系（SAR）研究。PCA和苯肼在M. phaseolina和C. truncatum中显示出相同的生长抑制百分比，而PCA（3）对C. nicotianae的活性低于苯肼。2-羟基苯肼（4）对M. phaseolina没有抗真菌活性。SAR研究的结果表明，电子吸引剂（COOH和NO2）或排斥剂（OH）基团显着影响抗真菌生长，以及它们在苯肼环上的α或β位置。PCA和苯肼都可以作为生物杀虫剂，用于控制大豆病原体M. phaseolina、C. nicotianae和C. truncatum，这些结果应促使对它们的大规模生产和适合温室和田间应用的适当配方进行研究。