Green synthesis method for high-yield preparation of trifloxystrobin

A technology for green synthesis and trifloxystrobin, which is applied in oxime preparation, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of low overall yield, large amount of inorganic waste salts, cumbersome work sections, etc., and improve the reaction rate. , The effect of reducing the amount of waste salt and improving the final yield

Pending Publication Date: 2021-03-23
利民化学有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the shortcomings of the prior art, such as large amount of inorganic waste salt, low overall yield, and cumbersome working sections, the present

Method used

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  • Green synthesis method for high-yield preparation of trifloxystrobin
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  • Green synthesis method for high-yield preparation of trifloxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 0.1 g of phosphine-containing ligand, 6 g of organic base DBU (1,8-diazabicycloundec-7-ene) and 20 ml of DMF into a 250 mL three-necked flask, stir to dissolve, and cool down to 0°C. After cooling, a mixed solution of 2-bromomethyl-(αE)methoxyiminophenylacetic acid methyl ester (12.6g, 0.04mol) and m-trifluoromethylacetophenone oxime (9.8g, 0.048mol) was added dropwise (contains DMF40ml), temperature controlled at 5°C and added dropwise. After the dropwise addition, keep warm for 10 minutes, then raise the temperature to 15°C and keep warm for 2 hours. After the completion of the detection reaction, cool down to room temperature and slowly add 160ml of water to it, continue to stir, a white solid precipitates out, filter and drain to obtain 17.4g of crude product. The crude product was dissolved in 60ml of ethanol, recrystallized to obtain 16.6g of pure white solid, the purity determined by liquid chromatography was 96.84%, and the yield was 92.4%.

[0028] The NM...

Embodiment 2

[0031] Add 0.05 g of phosphine-containing ligand, 6 g of organic base DBU (1,8-diazabicycloundec-7-ene) and 20 ml of DMF into a 250 mL three-necked flask, stir to dissolve, and cool down to 0°C. After cooling, a mixed solution of 2-bromomethyl-(αE)methoxyiminophenylacetic acid methyl ester (12.6g, 0.04mol) and m-trifluoromethylacetophenone oxime (9.8g, 0.048mol) was added dropwise (contains DMF40ml), temperature controlled at 5°C and added dropwise. After the dropwise addition, keep warm for 10 minutes, then raise the temperature to 15°C and keep warm for 2 hours. After the completion of the detection reaction, cool down to room temperature and slowly add 160ml of water to it, continue to stir, a white solid precipitates out, filter and drain to obtain 17g of crude product. The crude product was dissolved in 60 ml of ethanol, and recrystallized to obtain 16.1 g of pure white solid. The purity determined by liquid chromatography was 96.2%, and the yield was 92%.

[0032] The ...

Embodiment 3

[0035] Add 0.1 g of phosphine-containing ligand, 4.2 g of organic base DBU (1,8-diazabicycloundec-7-ene) and 20 ml of DMF into a 250 mL three-necked flask, stir to dissolve, and cool down to 0°C. After cooling, a mixed solution of 2-bromomethyl-(αE)methoxyiminophenylacetic acid methyl ester (12.6g, 0.04mol) and m-trifluoromethylacetophenone oxime (9.8g, 0.048mol) was added dropwise (contains DMF40ml), temperature controlled at 5°C and added dropwise. After the dropwise addition, keep warm for 10 minutes, then raise the temperature to 15°C and keep warm for 2 hours. After the completion of the detection reaction, cool down to room temperature and slowly add 160ml of water to it, continue to stir and a white solid precipitates out, filter and drain to obtain 16.8g of crude product. The crude product was dissolved in 60ml of ethanol, and recrystallized to obtain 16g of pure white solid. The purity determined by liquid chromatography was 96.2%, and the yield was 91.1%.

[0036] ...

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Abstract

The invention discloses a green synthesis method for high-yield preparation of trifloxystrobin. The method comprises the following steps that methyl 2-bromomethyl-(alpha E) methoxyiminobenzene acetateis condensed with m-trifluoromethyl acetophenone oxime under the dual catalytic action of a phosphine-containing ligand catalyst and DBU serving as alkali to generate the high-yield trifloxystrobin.The reaction conditions for preparing trifloxystrobin are milder, the reaction time is short, the use amount of the solvent is small, inorganic base is adopted, and the amount of waste salt is reduced. And the fully-dissolved state of the material can be used for a micro-channel reactor. The method has the advantages of simple steps, environmental protection, suitableness for industrial production, high yield and high content of the final product, and production cost reduction.

Description

technical field [0001] The invention relates to the preparation of fine chemical products, in particular to a green synthesis method for preparing trifloxystrobin with high yield. Background technique [0002] The chemical name of trifloxystrobin is E-methoxyimino-(2-(1-(3-trifluoromethylphenyl)-E-ethyleneamineoxymethyl)phenyl)methyl acetate, which is a Methoxyacrylate-like fungicides. As a new type of agricultural fungicide, trifloxystrobin has the characteristics of low toxicity, high efficiency and environmental friendliness. By locking the electron transfer of cytochrome b and c1 on the inner membrane of mitochondria, it blocks the transfer of electrons in the respiratory chain, thereby preventing the synthesis of ATP and hindering fungal respiration. The unique mechanism of action of trifloxystrobin makes it have a broad bactericidal spectrum and high activity. It has good activity against almost all fungal diseases including powdery mildew, rust, net spot, etc., and...

Claims

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Application Information

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IPC IPC(8): C07C251/60C07C249/04B01J19/00
CPCC07C249/04B01J19/0093C07B2200/13C07C251/60
Inventor 许辉李林虎李新生孙敬权许宜伟孙丽梅石卫
Owner 利民化学有限责任公司
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