Method for synthesizing chlorantraniliprole

A technology for chlorantraniliprole and a synthesis method, which is applied in the legal field of chlorantraniliprole, can solve problems such as poor atom economy, three wastes, and cumbersome treatment process, and achieves the effect of increasing treatment cost

Active Publication Date: 2021-03-30
JIANGSU KUAIDA AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Both methods use methanesulfonyl chloride and 3-picoline to react, and the amount is more than 1 times the equivalent, methanesulfonyl chloride is expensive, and methan

Method used

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  • Method for synthesizing chlorantraniliprole
  • Method for synthesizing chlorantraniliprole
  • Method for synthesizing chlorantraniliprole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Step A: 2-(3-Bromo-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl)-6-chloro-8-methyl-4H-benzo[d][1 ,3] Synthesis of oxazin-4-one

[0025] In a 100ml three-necked flask, configure a condenser, add 45ml of acetonitrile, cool down to 0°C, inject 10g of phosgene, and keep warm at 0-5°C for later use. In a 250ml four-necked flask, add 50ml of acetonitrile, 9g of 3-picoline, 15g of 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, 9.2g of 2 -Amino-5-chloro-3-methylbenzoic acid, cooled down to 0°C under stirring, began to add dropwise phosgene acetonitrile solution, controlled the reaction temperature at 0-5°C, after 3h dropwise addition, kept the temperature at room temperature for 1h to obtain The yellow suspension was bubbled with nitrogen for 1 h, and then filtered with suction to obtain a yellow wet product, which was directly used in the next step of synthesis without purification.

[0026] Step B: the synthesis of chlorantraniliprole

[0027] In a 250ml four-neck ...

Embodiment 2～4

[0029] According to the method of steps A and B in Example 1, different solvents in step A are replaced, and the solvent added is 45ml dissolved phosgene, and the solvent (which is the same solvent as dissolved phosgene) is 50ml mixed organic base, 3-bromo- 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, 2-amino-5-chloro-3-methylbenzoic acid, reaction conditions and results are as shown in table 1, it can be seen that adopt Acetonitrile had the best effect as a solvent, and the purity and yield of chlorantraniliprole were the highest.

[0030] The reaction conditions and result contrast of table 1 embodiment 2-4

[0031]

Embodiment 5～7

[0033] According to the method of steps A and B in Example 1, adjust the reaction temperature in step A. The reaction conditions and results are shown in Table 2. It can be seen that the reaction temperature is the best when the reaction temperature is 0-5 ° C. The yield of chlorantraniliprole and high purity.

[0034] The reaction condition of table 2 embodiment 5-7 and result contrast

[0035]

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PUM

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Abstract

The invention discloses a synthesis method of chlorantraniliprole, which comprises the following steps: dissolving phosgene in a solvent to form a material A, mixing 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid and 2-amino-5-chloro-3-methylbenzoic acid as raw materials in the presence of alkali and the solvent, and adding the material A to carry out a reaction to obtain 2-(3-Bromo-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazine-4-one (oxazinone, for short), and directly reacting the oxazinone with monomethylamine without purification to synthesize the chlorantraniliprole. The synthesis method has the advantages of cheap raw materials, high reaction activity, simple post-treatment process and no residue; the reaction synthesis conditions aremild, less three wastes are generated, special equipment is not needed, and industrial production is easy to realize.

Description

technical field [0001] The invention relates to the technical field of a synthetic process of an insecticide, more specifically to a legal method of chlorantraniliprole. Background technique [0002] Chlorantraniliprole (Chlorantraniliprole) is a new type of low-toxicity, high-efficiency bisamide-based insecticide developed by DuPont of the United States. The trade name is Kangkuan. The compound has a brand-new mechanism of action. By activating the ryanodine receptor, the receptor channel is opened abnormally for a long time, resulting in unlimited calcium ion release, calcium pool failure, muscle paralysis, and eventual death. It has good activity and long-lasting effect Long and other advantages. Chlorantraniliprole has a wide insecticidal spectrum, can be used for a variety of crops, has low toxicity, and is environmentally safe. In 2016, it was the world's largest insecticide with sales of 1.365 billion US dollars and the third largest for rice. Insecticides consolida...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D401/04
CPCC07D413/14C07D401/04
Inventor 吴锋黄志红
Owner JIANGSU KUAIDA AGROCHEM
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