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A kind of indazole compound and its preparation method and application

A technology of compound and indazole, which is applied in the field of indazole compound and its preparation and application, and can solve problems such as unsuccessful development

Active Publication Date: 2018-05-15
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, commercialized protoporphyrinogen oxidase inhibitors are all developed by major pesticide companies in Europe and America, and there is no report of successful development in China

Method used

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  • A kind of indazole compound and its preparation method and application
  • A kind of indazole compound and its preparation method and application
  • A kind of indazole compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] This embodiment is used to illustrate the preparation method of the indazole compound of the present invention

[0085] Indazole compounds of the present invention are synthesized through the following synthetic routes:

[0086]

[0087] 1) Synthesis of compound 2

[0088] In a 500 mL three-necked flask, 2,4-difluoroaniline (100 mmol) was dissolved in 200 mL of concentrated hydrochloric acid. Keeping the external temperature of the system at -9°C, a mixed solution of sodium nitrite (8.28 g, 120 mmol) and water (50 mL) was slowly added dropwise to the above system, and the addition was completed within 25 minutes. After stirring for about 1 hour, the SnCl 2 A mixed solution of (45.1g, 200mmol) and concentrated hydrochloric acid (100mL) was slowly added dropwise to the above system, and the dropwise addition was completed within 2h. Afterwards, the ice-salt bath was continued to keep the reaction at low temperature for 2 hours, and then filtered, and the filter resi...

Embodiment 2

[0117] This embodiment is used to illustrate the preparation method of the indazole compound of the present invention

[0118] According to the method in Example 1, the difference is that in step 1, 2,4-difluoroaniline is replaced by 2,4-dichloroaniline, to obtain the target compounds I-15~I-27 shown in Table 1 .

[0119] The confirmed data of compounds I-15~I-27 are as follows:

[0120] I-15: solid; m.p.155-156°C. 1 H NMR (600MHz, CDCl 3 )δ7.90(s,1H),7.86(s,1H),4.24(q,J=7.2Hz,2H),4.16(s,2H),2.74(d,J=6.0Hz,2H),2.55( d, J=6.0Hz, 2H), 1.85(q, J=6.0Hz, 4H), 1.29(t, J=7.2Hz, 3H).ESI-MS: 464.1(M+Na) + .

[0121] I-16: solid; m.p.102-103°C. 1 H NMR (600MHz, CDCl 3 )δ7.88(s,1H),7.87(s,1H),4.19(q,J=7.1Hz,2H),3.61(t,J=7.2Hz,2H),2.91(t,J=7.2Hz, 2H), 2.75(t, J=6.0Hz, 2H), 2.54(t, J=6.0Hz, 2H), 1.85(dd, J=6.6Hz, 4H), 1.28(t, J=7.2Hz, 3H) .ESI-MS: 478.2 (M+Na) + .

[0122] I-17: solid; 1 H NMR (600MHz, CDCl 3 )δ7.88(s,1H),7.86(s,1H),4.15(q,J=7.2Hz,2H),3.42(t,J=7.2Hz,2H),2.74(t...

Embodiment 3

[0134] This embodiment is used to illustrate the preparation method of the indazole compound of the present invention

[0135] According to the method in Example 1, the difference is that 2,4-difluoroaniline is replaced by 2-bromo-4-fluoroaniline in step 1 to obtain the target compounds I-28~I- 40.

[0136] The confirmed data of compounds I-28~I-40 are as follows:

[0137] I-28: solid; m.p.108-110°C. 1 H NMR (600MHz, CDCl 3 )δ8.07(s,1H),7.85(s,1H),4.24(q,J=7.2Hz,2H),4.16(s,2H),2.75(s,2H),2.54(s,2H), 1.85(q, J=6.0Hz, 4H), 1.29(t, J=7.2Hz, 3H).ESI-MS: 486.2(M+H) + .

[0138] I-29: solid; m.p.108-109°C. 1 H NMR (600MHz, CDCl 3 )δ8.05(s,1H),7.86(s,1H),4.18(q,J=7.2Hz,2H),3.61(t,J=7.2Hz,2H),2.91(t,J=7.2Hz, 2H), 2.74(t, J=6.0Hz, 2H), 2.54(t, J=6.0Hz, 2H), 1.85(q, J=6.0Hz, 4H), 1.27(t, J=7.2Hz, 3H) .ESI-MS:522.1(M+Na) + .

[0139] I-30::Oil. 1 H NMR (600MHz, CDCl 3 )δ8.05(s,1H),7.85(s,1H),4.15(q,J=7.2Hz,2H),3.42(t,J=7.2Hz,2H),2.76(t,J=6.0Hz, 2H), 2.54(t, J=6.0Hz, 2H), 2....

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Abstract

The invention discloses an indazole compound, which is characterized in that the indazole compound is a compound with the structure shown in the following general formula (1), in the formula (1), R is selected from the group with 2-6 carbon atoms Alkenyl, alkynyl with 2-6 carbon atoms, carboxyl with 2-6 carbon atoms or ester group with 2-10 carbon atoms; X1 is selected from halogen; X2 is selected from Cl or Br. The indazole compounds provided by the invention have high herbicidal activity.

Description

technical field [0001] The invention relates to an indazole compound, a preparation method and application thereof. Background technique [0002] Protoporphyrinogen oxidase inhibitors (Protox / PPO inhibitors) are a class of herbicides with a special mechanism of action. Protoporphyrinogen IX quickly accumulates and overflows into the cytoplasm, and becomes photosensitive protoporphyrin IX under the action of non-enzymatic mechanisms or other enzymes. Protoporphyrin IX absorbs energy under the action of light to become an excited state, and converts energy Passed to the oxygen molecule, making it generate singlet oxygen O 1 , Under the action of singlet oxygen, the cell membrane undergoes peroxidation reaction and is destroyed, which causes cell death and eventually leaves death. Due to the unique mechanism of action of protoporphyrinogen oxidase inhibitors, resistance is slow to develop. At the same time, this type of herbicide has a very broad-spectrum herbicidal activity ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A01N43/78A01P13/00
Inventor 杨光富左炀
Owner HUAZHONG NORMAL UNIV