N-(5-amino-4-chloro-2-fluorophenyl)phthalimide | 255366-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(5-amino-4-chloro-2-fluorophenyl)phthalimide
• 英文别名: 2-(5-amino-4-chloro-2-fluorophenyl)isoindole-1,3-dione
• CAS: 255366-50-8
• 化学式: C₁₄H₈ClFN₂O₂
• 分子量: 290.681
• InChiKey: GOUXUSLRKAYSMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-amino-4-chloro-2-fluorophenyl)phthalimide 、 potassium ethyl xanthogenate 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到2-(2-mercapto-6-fluorobenzothiazol-5-yl)isoindoline-1,3-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：

  4-氯-2-氟苯胺 在 硫酸 、 硝酸 、 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.25h， 生成 N-(5-amino-4-chloro-2-fluorophenyl)phthalimide
  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

文献信息

• Phthalimides and herbicide containing the same as active component
  申请人：Mitsubishi Chemical Corporation

  公开号：US06365753B1

  公开（公告）日：2002-04-02

  A phthalimide represented by general formula (I): wherein L represents L-1 or L-2: (wherein R1 and R2 each independently represent a hydrogen atom, an alkyl group, etc.); A represents an oxygen atom, a sulfur atom or —NR5— (wherein R5 is a hydrogen atom, an alkyl group, an alkenyl group, etc.); R represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a phenyl group, etc.; X represents a halogen atom; Y represents a hydrogen atom or a halogen atom; and Z represents a hydrogen atom, an alkyl group, a haloalkyl group or a halogen atom. The compound exhibits excellent herbicidal effects with high selectivity.

  一种以通式（I）表示的邻苯二甲酰亚胺：其中L代表L-1或L-2：（其中R1和R2各自独立地代表氢原子、烷基基团等）；A代表氧原子、硫原子或-NR5-（其中R5代表氢原子、烷基基团、烯基基团等）；R代表氢原子、烷基基团、烯基基团、环烷基团、苯基等；X代表卤素原子；Y代表氢原子或卤素原子；Z代表氢原子、烷基基团、卤代烷基基团或卤素原子。该化合物表现出优异的除草效果，并具有高选择性。
• PHTHALIMIDES AND HERBICIDE CONTAINING THE SAME AS ACTIVE COMPONENT
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1097923A1

  公开（公告）日：2001-05-09

  Phthalimides represented by general formula (I), wherein L represents a group represented by the following L-1 or L-2, wherein each of R1 and R2 is independently a hydrogen atom, an alkyl group or the like, A represents an oxygen atom, a sulfur atom or -NR5- wherein R5 is a hydrogen atom, an alkyl group, an alkenyl group or the like, R represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a phenyl group or the like, X represents a halogen atom, Y represents a hydrogen atom or a halogen atom, and Z represents a hydrogen atom, an alkyl group, a haloalkyl group or a halogen atom. Such phthalimides have high herbicidal effect and also high selectivity.

  由通式(I)代表的邻苯二甲酰亚胺，其中 L 代表由下述 L-1 或 L-2 所代表的基团，其中 R1 和 R2 各自独立地为氢原子、烷基或类似基团，A 代表氧原子、硫原子或-NR5-，其中 R5 为氢原子、烷基、烯基或类似基团，R 代表氢原子、烷基、烯基、环烷基、苯基或类似基团，X 代表卤素原子，Y 代表卤素基团、R 代表氢原子、烷基、烯基、环烷基、苯基或类似基团，X 代表卤素原子，Y 代表氢原子或卤素原子，Z 代表氢原子、烷基、卤代烷基或卤素原子。此类邻苯二甲酰亚胺具有很高的除草效果和选择性。
• US6365753B1
  申请人：——

  公开号：US6365753B1

  公开（公告）日：2002-04-02
• Design and Syntheses of Novel<i>N</i>-(Benzothiazol-5-yl)-4,5,6,7-tetrahydro-1<i>H</i>-isoindole-1,3(2<i>H</i>)-dione and<i>N</i>-(Benzothiazol-5-yl)isoindoline-1,3-dione as Potent Protoporphyrinogen Oxidase Inhibitors
  作者：Li-Li Jiang、Yang Zuo、Zhi-Fang Wang、Yin Tan、Qiong-You Wu、Zhen Xi、Guang-Fu Yang

  DOI：10.1021/jf200616y

  日期：2011.6.8

  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.