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Preparation method of chlorantraniliprole

A technology for chlorantraniliprole and compound, which is applied in the field of preparation of chlorantraniliprole, can solve the problems of large harm to production operators, reduced comprehensive cost, high equipment investment, etc. low cost effect

Pending Publication Date: 2022-03-25
江苏七洲绿色科技研究院有限公司 +1
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  • Abstract
  • Description
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Problems solved by technology

[0005] In the existing preparation process of chlorantraniliprole, 3-picoline is mostly used as the base. Since 3-picoline is miscible with water, it is difficult to recover from water later, and it has not been found in the literature. Associated recovery options, which may require rectification
At the same time, acetonitrile is mostly used as a solvent in the existing preparation methods. Acetonitrile and water are miscible, and subsequent recovery from water is also difficult. The recovery scheme reported in the literature is twice rectification, and the second is negative pressure rectification.
It can be seen that the recovery of alkali and solvent in the original process requires rectification, which requires high equipment investment, high technical difficulty and high energy consumption, which is not conducive to the reduction of overall cost
[0006] In addition, the existing process uses methanesulfonyl chloride as a condensation reagent to activate 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid, methanesulfonyl chloride is a highly toxic drug, transport And the use is strictly controlled, and it is also more harmful to production operators

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  • Preparation method of chlorantraniliprole
  • Preparation method of chlorantraniliprole
  • Preparation method of chlorantraniliprole

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[0032] The preparation method of chlorantraniliprole in the prior art needs to recover the alkali and the solvent, all of which require rectification, requires high equipment investment, high technical difficulty and high energy consumption, which is not conducive to the reduction of comprehensive costs; There is a process that uses methylsulfonyl chloride as a condensation reagent to activate 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid. Methanesulfonyl chloride is a highly toxic drug, and it is safe to transport and use. Strictly controlled, it is also more harmful to production operators.

[0033] In order to solve the above problems, we have discovered a class of boric acid catalysts that can be used as a catalyst for the synthesis of chlorantraniliprole. In a high-temperature hydrophobic solvent, chlorantraniliprole can be successfully synthesized by using a water separator to separate water.

[0034] Specifically, in the present invention, in the presenc...

Embodiment 1

[0040] In the reaction flask, add 150g toluene, 50g 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid (compound shown in formula I), 33.16g 2-amino-5- Chloro-n,3-dimethylbenzamide (compound represented by formula II), 7.5g of boric acid, put the system in an oil bath at 120°C for 6 hours, and use a water separator to separate water while reacting. After the content of 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid is lower than 0.5%, stop the reaction, after the reaction system is down to room temperature, filter, rinse with 30g toluene, Rinse with 30g of water, beat the product with 100g of methanol, filter and dry to obtain 56.13g of off-white solid with a yield of 70.3%, which is chlorantraniliprole.

Embodiment 2

[0042] Add 150g toluene, 50g 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid, 33.16g 2-amino-5-chloro-n,3-dimethyl to the reaction flask phenylbenzamide, 7.5g 3-nitrophenylboronic acid, put the system in an oil bath at 120°C to react for 5 hours, use a water separator for the reaction, separate water while reacting, and control 3-bromo-1-(3- After the content of chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid is lower than 0.5%, stop the reaction, after the system is down to room temperature, filter, rinse with 30g toluene, rinse with 30g water, and then use 100g methanol to beat the product, After filtration and drying, 59.56 g of off-white solid was obtained, with a yield of 74.6%.

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Abstract

The invention discloses a preparation method of chlorantraniliprole. According to the process, a boric acid substance is used as a condensation catalyst, and in a hydrophobic solvent and at a high temperature, 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid and 2-amino-5-chloro-n, 3-dimethyl benzamide react while water is separated to prepare chlorantraniliprole. The preparation method provided by the invention solves the difficult problem of acetonitrile recovery and also solves the difficult problem of 3-methylpyridine recovery, and more importantly, a highly toxic control product methylsulfonyl chloride is not used any more; the preparation method disclosed by the invention is clean, less in discharge of three wastes, simple and convenient to operate, relatively low in cost and relatively high in industrial production value.

Description

technical field [0001] The invention relates to the field of pesticide fungicides, in particular to a preparation of chlorantraniliprole. Background technique [0002] Chlorantraniliprole is the largest variety of insecticides. It was developed and listed by DuPont in 2008. It currently belongs to FMC. Its structural formula is: [0003] [0004] Chlorantraniliprole won the Most Innovative Chemistry Award at the Brighton World Crop Protection Congress on October 16, 2007. Chlorantraniliprole is widely used in rice, grain, corn, soybean and other bulk crops, and can effectively control Lepidoptera, Coleoptera, Diptera, Hemiptera and termite insects. It is safe to natural enemies, safe to mammals, low-toxic to bees, fish, and shrimp, and resistant to rainwater erosion. The effective period can reach more than 15 days, and it has good mixing performance with other pesticides. The product sells well in 110 countries around the world, with sales of 1.75 billion US dollars in...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 徐秋龙姚中伟吕国雨
Owner 江苏七洲绿色科技研究院有限公司
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