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Pyridazinone compound and synthesis method thereof

A synthetic method and technology of pyridazinone, which is applied in the field of organic chemical synthesis, can solve problems such as application limitations, and achieve the effects of wide application range, good application prospects, and easy availability of raw materials

Inactive Publication Date: 2018-09-07
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, during the long-term use of pyridazine compounds, the resistance of pests and pathogens to them has been continuously enhanced, which limits their application in agriculture.

Method used

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  • Pyridazinone compound and synthesis method thereof
  • Pyridazinone compound and synthesis method thereof
  • Pyridazinone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] One pyridazinone compound, the compound molecular formula is as follows:

[0037]

[0038] Among them, R 1 is methyl, R 2 is methyl, R 3 is piperidinyl; R 4 for chlorine. The synthetic method of this pyridazinone compound comprises the following steps:

[0039] (1) Synthesis of α-chloroacetophenone

[0040]

[0041] Add 200mL of o-xylene and 74.40g (0.557mol) of anhydrous aluminum chloride into a 250mL three-necked flask with a drying device, cool in an ice-water bath, and then slowly add 60.0g (0.531mol) of α-chloride Substituting acetyl chloride, after the dropwise addition was completed, react at room temperature for 3 hours, and stop stirring. The reaction solution was poured into a beaker filled with 200 mL of ice water and stirred, extracted with ethyl acetate and separated, the organic phase was washed with water until neutral, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 76.17 g of a white soli...

Embodiment 2

[0052] One pyridazinone compound, the compound molecular formula is as follows:

[0053]

[0054] Among them, R 1 is methyl, R 2 is methyl, R 3 for morpholine, R 4 for chlorine. The synthetic method of this pyridazinone compound comprises the following steps:

[0055] (1) Synthesis of α-chloroacetophenone

[0056]

[0057] Add 200mL of o-xylene and 74.40g (0.557mol) of anhydrous aluminum chloride into a 250mL three-necked flask with a drying device, cool in an ice-water bath, and then slowly add 60.0g (0.531mol) of α-chloride Substituting acetyl chloride, after the dropwise addition was completed, react at room temperature for 3 hours, and stop stirring. The reaction solution was poured into a beaker filled with 200 mL of ice water and stirred, extracted with ethyl acetate and separated, the organic phase was washed with water until neutral, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 76.17 g of a white soli...

Embodiment 3

[0065] One pyridazinone compound, the compound molecular formula is as follows:

[0066]

[0067] Among them, R 1 is methyl, R 2 is methyl, R 3 is n-propylamino, R 4 for chlorine. The synthetic method of this pyridazinone compound comprises the following steps:

[0068] (1) Synthesis of α-chloroacetophenone

[0069]

[0070] Add 200mL of o-xylene and 74.40g (0.557mol) of anhydrous aluminum chloride into a 250mL three-necked flask with a drying device, cool in an ice-water bath, and then slowly add 60.0g (0.531mol) of α-chloride Substituting acetyl chloride, after the dropwise addition was completed, react at room temperature for 3 hours, and stop stirring. The reaction solution was poured into a beaker filled with 200 mL of ice water and stirred, extracted with ethyl acetate and separated, the organic phase was washed with water until neutral, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 76.17 g of a white so...

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Abstract

The present invention relates to a pyridazinone compound and a synthesis method thereof, wherein the general formula of the compound is defined in the specification, R<1> is C1-C4 alkyl or halogen, R<2> is C1-C4 alkyl or halogen, R<3> is linear chain fatty amine or cyclic amine or propylthio or aromatic methoxy, and R<4> is halogen or propylthio. The preparation method comprises: carrying out a Friedel-Crafts reaction on halogenated acetyl halide and benzene to synthesize alpha-halogenated acetophenone, carrying out a substitution reaction on the alpha-halogenated acetophenone and 4,5-dichloro-3(2H)-pyridazinone to synthesize an intermediate, and carrying out a substitution reaction on the generated intermediate and a nucleophilic reagent such as fatty amine or cyclic fatty amine or propanethiol under the catalysis of an alkaline reagent to synthesize the pyridazinone compound. Compared to the method in the prior art, the method of the present invention has advantages of simple process, good repeatability, simple and easily-available raw materials, wide application range and good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a pyridazinone compound and a synthesis method thereof. Background technique [0002] Pesticides mainly refer to chemical drugs used to prevent various diseases (pests, pests, nematodes, pathogens, weeds and rodents) and regulate plant growth in agricultural, forestry and animal husbandry production. However, the large-scale use of traditional pesticides has negative impacts on the environment and leads to the resistance of pathogenic microorganisms and pests, which greatly reduces the application ability. affect the development of the national economy. [0003] Pyridazine compounds are a class of heterocyclic compounds with high-efficiency herbicidal, insecticidal and acaricidal activities, and plant growth regulation. Many species also have the characteristics of low toxicity and low residue. At present, pyridazinone compounds are widely used in the control o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/14C07D401/04C07D237/22C07D237/18
CPCC07D237/14C07D237/18C07D237/22C07D401/04
Inventor 李洪森孙艳文邬浩蕾韦昌恒高美沈泽宜
Owner SHANGHAI UNIV OF ENG SCI
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