N-hydroxy-3-trifluoromethylthiobenzimidic acid methyl ester | 1612238-37-5

• 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: N-hydroxy-3-trifluoromethylthiobenzimidic acid methyl ester
• 英文别名: methyl N-hydroxy-3-(trifluoromethyl)benzenecarboximidothioate
• CAS: 1612238-37-5
• 化学式: C₉H₈F₃NOS
• 分子量: 235.23
• InChiKey: WEKQPPDSJXAIJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-bromomethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one 、 N-hydroxy-3-trifluoromethylthiobenzimidic acid methyl ester 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以0.07 g的产率得到N-[2-methyl-6-(4-methoxy-5-oxo-4,5-dihydrotetrazol-1-yl)benzoyloxy]-3-trifluoromethylthiobenzimidic acid methyl ester
  参考文献：
  名称：

  TETRAZOLINONE COMPOUND AND USE THEREOF

  摘要：

  公开号：

  EP2927218B1

文献信息

• Synthesis and Evaluation O-Benzyl Oxime-ether Derivatives Containing β-Methoxyacrylate Moiety for Insecticidal and Fungicidal Activities
  作者：Zhi-Bin Hu、He-An Luo、Xiao-Guang Wang、Ming-Zhi Huang、Lu Huang、Huai-Lin Pang、Chun-Hui Mao、Hui Pei、Chao-Qun Huang、Jiong Sun、Ping-Le Liu、Ai-Ping Liu

  DOI：10.5012/bkcs.2014.35.4.1073

  日期：2014.4.20

  In attempt to lead compounds exhibiting both insecticidal and fungicidal activities, a series of O-benzyl oximeether derivatives were designed and synthesized by introducing $\beta}$-methoxyacrylate pharmacophore into a scaffold. The insecticidal activity against Aphis fabae and the fungicidal activity against Erysiphe graminis were screened. The title compounds exhibited remarkable insecticidal and fungicidal activities. The most potent compound 6d was identified. Its insecticidal $LC_50}$ against A. fabae is 6.4 mg/L, which is lower than that of chlorfenapyr (19.4 mg/L) and even close to the level of imidacloprid (4.8 mg/L). Its fungicidal $EC_90}$ in preventive and curative treatment against E. graminis are 2.2 and 4.8 mg/L, respectively, which are lower than azoxystrobin (7.0 and 5.9 mg/L). These results indicate that compound 6d can be considered as a lead for further developing new O-benzyl oxime-ether typed candidates with both fungicidal and insecticidal activities.

  为了找到同时具有杀虫和杀菌活性的化合物，我们在支架中引入了$\beta}$-甲氧基丙烯酸酯药架，设计并合成了一系列 O-苄基肟醚衍生物。筛选了这些化合物对蚜虫的杀虫活性和对禾谷镰刀菌的杀菌活性。标题化合物表现出显著的杀虫和杀真菌活性。鉴定出了最强效的化合物 6d。它对蚕蛾的杀虫 $LC_50}$ 为 6.4 mg/L，低于氯虫苯甲酰胺（19.4 mg/L），甚至接近吡虫啉（4.8 mg/L）的水平。在预防和治疗禾谷英病菌方面，其杀菌$EC_90}$分别为 2.2 和 4.8 mg/L，低于唑啉草酯（7.0 和 5.9 mg/L）。这些结果表明，化合物 6d 可作为进一步开发具有杀菌和杀虫活性的新型 O-苄基肟醚类候选化合物的先导。