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Preparation method of topramezone

A technology of fenflumezone and hydroxypyrazole, which is applied in the field of preparation of fenflumezone, can solve the problems of increasing the difficulty of industrial production, the danger of storage, transportation and feeding, and the difficult treatment of three wastes. Low, non-toxic and side effects

Active Publication Date: 2020-12-25
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In this method, a large amount of refractory three wastes are also generated due to steps such as oximation, diazotization, and carbonyl insertion, which pollute the environment.
At the same time, Class I combustibles are also used in the diazotization process. Storage, transportation and feeding are very dangerous and cumbersome, which increases the difficulty of industrial production.

Method used

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  • Preparation method of topramezone
  • Preparation method of topramezone
  • Preparation method of topramezone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]

[0077] Add 20g of o-xylene into a 250ml three-neck flask (including a stirrer and a thermometer) with 100g of ethanol, stir to lower the temperature, and when the temperature reaches 0°C, start to slowly introduce chlorine gas, control the temperature to less than 10°C, and detect the concentration of the reaction solution by gas phase. O-xylene content, stop feeding chlorine gas when reaching the end of the reaction, dedry the ethanol under negative pressure to obtain 30.8g of crude product, the gas phase detection purity is 95%, no need for purification, directly used in the next step reaction.

Embodiment 2

[0079]

[0080] The crude product 30.8g that embodiment 1 gained is transferred in the 250ml there-necked flask (containing stirring bar and thermometer), adds 150g acetonitrile, adds copper acetate (3.0g, 0.1eq) after dissolving, N-hydroxysuccinimide (3.9g , 0.2eq), under vacuum nitrogen protection, dropwise added tert-butyl nitrite (51.7g, 3.3eq), and under nitrogen protection, the temperature was raised to 75°C, and the reaction was kept for 8h. The liquid phase detection showed that the reaction was complete, and the acetonitrile was dried , add 50g of water for rinsing, drain as much as possible, add 50g of toluene for rinsing, and dry to obtain 28.6g of the target object, with a liquid phase detection purity of 94.8%.

Embodiment 3

[0082]

[0083] Transfer 28.6 g of the product obtained in Example 2 to a 250 ml three-neck flask (including a stirrer and a thermometer), add 90 g of dichloroethane, replace nitrogen 3 times, and replace nitrogen 5 times with ethylene gas, and control the temperature at 20°C to 30°C Thionyl chloride (31.6g, 2eq) was added dropwise, and kept at this temperature for 4h. The liquid phase detection showed that the reaction was complete, and 30g of water was added to separate the layers. The lower layer was washed twice with saturated sodium carbonate, 10g each time, and washed with water for 2 times, 10g each time, after being dried over sodium sulfate, the solvent was removed, rinsed with 20g of petroleum ether, and dried to obtain 27.2g of the target substance, with a liquid phase detection purity of 91%.

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Abstract

The invention relates to a preparation method of topramezone. Themethod comprises the following steps of: (1) carrying out oxidation reaction on a compound 5 and an oxidant under the action of a catalyst to obtain a compound 6; (2) carrying out Grignard reaction on the compound 6, magnesium and carbon dioxide to obtain a compound 7; and (3) carrying out condensation reaction on the compound 7 and1-methyl-5-hydroxy pyrazole to obtain topramezone. The structural formula of the compound 5, the structural formula of the compound 6, the structural formula of the compound 7 are described in descriptions of the invention. The preparation method of topramezone has the advantages of few by-products, high purity and yield of topramezone, low wastewater treatment difficulty, low cost, no toxic or side effect in the production process and suitability for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering, and in particular relates to a preparation method of fenfentrazone. Background technique [0002] Bentrazone, English common name: topramezone, chemical name: [3-(4,5-dihydro-3-isoxazolyl)-4-methylsulfonyl-2-methylbenzene]5-hydroxy- 1-methyl-1H-pyrazol-4-yl)methanone is a kind of benzyl pyrazolone herbicide, which has broad herbicidal spectrum, high activity, strong miscibility, wide application period, and It has the advantages of being safe to corn and subsequent crops. The mechanism of action of the herbicide is to inhibit the activity of p-hydroxyphenylpyruvate dioxygenase (HPPD), thereby interfering with the synthesis of carotene, interfering with the function of chloroplast, and finally leading to the death of weeds, so it is safe for animals. The weeds that fenpyrazone can effectively control include: crabgrass, barnyardgrass, goosegrass, wild millet, foxtail, ...

Claims

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Application Information

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IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 纪雷周炜陶亚春盛莹盈陈极
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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