6-chloro-2-mercapto-5-aminobenzothiazole | 1304684-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-chloro-2-mercapto-5-aminobenzothiazole
• 英文别名: 5-amino-6-chloro-3H-1,3-benzothiazole-2-thione
• CAS: 1304684-85-2
• 化学式: C₇H₅ClN₂S₂
• 分子量: 216.715
• InChiKey: BNSXPDJGQRTERE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4,5,6-四氢苯酐 、 6-chloro-2-mercapto-5-aminobenzothiazole 在 溶剂黄146 作用下， 反应 3.0h， 以77%的产率得到2-(6-chloro-2-mercaptobenzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Design and Syntheses of NovelN-(Benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione andN-(Benzothiazol-5-yl)isoindoline-1,3-dione as Potent Protoporphyrinogen Oxidase Inhibitors

  摘要：

  Discovery of protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors has been one of the hottest research areas in the field of herbicide development for many years. As a continuation of our research work on the development of new PPO-inhibiting herbicides, a series of novel N-(benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-diones (1 a p) and N-(benzothiazol-5-yl)isoindoline-1,3-diones (2a - h) were designed and synthesized according to the ring-closing strategy of two ortho-substituents. The bioassay results indicated that some newly synthesized compounds exhibited higher PPO inhibition activity than the control of sulfentrazone. Compound 1a, S-(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl) O-methyl carbonothioate, was identified as the most potent inhibitor with k(i), value of 0.08 mu M, about 9 times higher than that of sulfentrazone (k(i); = 0.72 mu M). Further green house assay showed that compound 1b, methyl 24(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)thio)acetate, exhibited herbicidal activity comparable to that of sulfentrazone even at a concentration of 37.5 g ai/ha. In addition, among six tested crops, wheat exhibited high tolerance to compound 1b even at a dosage of 300 g ai/ha. These results indicated that compound 1b might have the potential to be developed as a new herbicide for weed control of wheat field.

  DOI：

  10.1021/jf200616y
• 作为产物：
  描述：

  2,4-二氯-5-硝基-苯基胺 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-chloro-2-mercapto-5-aminobenzothiazole
  参考文献：
  名称：

  Design and Syntheses of NovelN-(Benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione andN-(Benzothiazol-5-yl)isoindoline-1,3-dione as Potent Protoporphyrinogen Oxidase Inhibitors

  摘要：

  Discovery of protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors has been one of the hottest research areas in the field of herbicide development for many years. As a continuation of our research work on the development of new PPO-inhibiting herbicides, a series of novel N-(benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-diones (1 a p) and N-(benzothiazol-5-yl)isoindoline-1,3-diones (2a - h) were designed and synthesized according to the ring-closing strategy of two ortho-substituents. The bioassay results indicated that some newly synthesized compounds exhibited higher PPO inhibition activity than the control of sulfentrazone. Compound 1a, S-(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl) O-methyl carbonothioate, was identified as the most potent inhibitor with k(i), value of 0.08 mu M, about 9 times higher than that of sulfentrazone (k(i); = 0.72 mu M). Further green house assay showed that compound 1b, methyl 24(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)thio)acetate, exhibited herbicidal activity comparable to that of sulfentrazone even at a concentration of 37.5 g ai/ha. In addition, among six tested crops, wheat exhibited high tolerance to compound 1b even at a dosage of 300 g ai/ha. These results indicated that compound 1b might have the potential to be developed as a new herbicide for weed control of wheat field.

  DOI：

  10.1021/jf200616y