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A kind of preparation method of fenfenzone

A kind of technology of oxaflutole and compound

Active Publication Date: 2022-03-18
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the main cost in the patented route provided by BASF lies in expensive palladium-based catalysts, and these precious metals are difficult to recover

Method used

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  • A kind of preparation method of fenfenzone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 10g (31.4mmol) of 3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4,5-dihydroisoxazole and 3.1g (31.4mmol) of 1-methyl -5-Hydroxypyrazole was dissolved in methanol, 0.2g (1.6mmol) of cobalt chloride was added, 5.1 (94.2mmol) of sodium methoxide was added, and the reaction was carried out at 80°C under 10bar CO for 8-11h, and the obtained reaction mixture naturally recovered to At room temperature, the solid matter was filtered off, and the separated organic liquid was washed with water, dried, and distilled to obtain 9.5 g of light yellow solid, namely fenmetrazone, with a purity of 91.1% and a yield of 83.2%.

Embodiment 2

[0027] 10g (31.4mmol) of 3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4,5-dihydroisoxazole and 3.1g (31.4mmol) of 1-methyl -5-Hydroxypyrazole was dissolved in methanol, 0.3g (1.6mmol) of cobalt acetate and 5.1g (94.2mmol) of sodium methoxide were added, and the reaction was carried out at 80°C under 10bar CO for 8-11h, and the obtained reaction mixture naturally recovered to At room temperature, the solid matter was filtered off, and the separated organic liquid was washed with water, dried, and distilled to obtain 9.7 g of light yellow solid, namely fenmetrazone, with a purity of 92.0% and a yield of 85.5%.

Embodiment 3

[0029] 10g (31.4mmol) of 3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4,5-dihydroisoxazole and 3.1g (31.4mmol) of 1-methyl -5-Hydroxypyrazole was dissolved in methanol, 0.3g (1.6mmol) of cobalt acetate and 6.6g (94.2mmol) of potassium methoxide were added, and the reaction was carried out at 80°C under 10bar CO for 8-11h, and the obtained reaction mixture naturally returned to room temperature , filtered off the solid matter, and the separated organic liquid was washed with water, dried, and distilled to obtain 10.2 g of a light yellow solid, namely fenmetrazone, with a purity of 94.9% and a yield of 89.7%.

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Abstract

The invention discloses a preparation method of fenflumezone. Compound I (3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4,5-dihydroisoxan azole) and compound II (1-methyl-5-hydroxypyrazole) react in the presence of an organic solvent, a base and a cobalt-based catalyst to obtain fenflumezone, and control the reaction temperature to 20-180°C. The preparation method used in the invention has simple operation, greatly reduced cost and high yield, and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and relates to a preparation method of fenfentrazone. Background technique [0002] Topramezon is the first benzopyrazolone herbicide developed by BASF. The drug belongs to the triketone post-emergence stem and leaf treatment agent. 4-HPPD, which indirectly affects the synthesis of carotenoids, thereby interfering with the synthesis and function of chloroplasts, eventually leading to severe albinism. It has a good control effect on weeds and can effectively control the main gramineous weeds and broadleaf weeds on corn crops worldwide. Benfentrazone has the advantages of broad herbicidal spectrum, high activity, strong mixability, and safety to corn and subsequent crops. At present, the drug is a hot drug developed in succession in China. However, the main cost of the patented route provided by BASF lies in expensive palladium-based catalysts, and these precious metals are diff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 夏易能姜宇华徐曦陈佳纪雷
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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