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Synthetic method of prothioconazole

A technology of prothioconazole and synthesis method, which is applied in the field of synthesis of new broad-spectrum triazole thione fungicides, can solve the problems of strong oxidation ability, desulfurization impurities, etc., and achieve the effect of avoiding the three wastes

Active Publication Date: 2020-06-19
JIANGYIN SULI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Patent CN 106986838A reports that hydrogen peroxide is used instead of ferric chloride as an oxidant, which has a certain effect, but the oxidation capacity of the hydrogen peroxide that oxidizes in the reaction is too strong, resulting in a large amount of desulfurization impurities

Method used

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  • Synthetic method of prothioconazole
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  • Synthetic method of prothioconazole

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Experimental program
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Effect test

Embodiment 1

[0029] Add 7.3g of intermediate A (95%, 20mmol), 20ml of ethanol and 0.066g (98%, 0.4mmol) of ferric chloride into the three-necked flask, cool to 20°C, and dropwise add 7.15g of hydrogen peroxide (10%, 21mmol) , the dropping time is 2 hours; after the dropwise addition, keep warm for 1 hour, add 50ml of water and 50ml of ethyl acetate, separate the liquids, extract the aqueous phase twice with 30ml of ethyl acetate, combine the organic phases, wash with 30ml of water three times, no Dry over sodium sulfate, concentrate under reduced pressure in vacuo to obtain 7.20 g of a light yellow solid, as determined by HPLC: the content of prothioconazole is 93.5%, the content of impurity B is 0.9%, and the yield is 97.6%.

Embodiment 2

[0031] Add 7.3g of intermediate A (95%, 20mmol), 20ml of tetrahydrofuran and 0.066g (98%, 0.4mmol) of ferric chloride into the three-necked flask, cool to 20°C, and dropwise add 7.15g of hydrogen peroxide (10%, 21mmol) , the dropping time is 2 hours; after the dropwise addition, keep warm for 1 hour, add 50ml of water and 50ml of ethyl acetate, separate the liquids, extract the aqueous phase twice with 30ml of ethyl acetate, combine the organic phases, wash with 30ml of water three times, no Dry over sodium sulfate, concentrate under reduced pressure in vacuo to obtain 7.17 g of a light yellow solid, as determined by HPLC: the content of prothioconazole is 92.7%, the content of impurity B is 0.8%, and the yield is 96.4%.

Embodiment 3

[0033] Add 7.3g of intermediate A (95%, 20mmol), 20ml of tetrahydrofuran and 0.099g (98%, 0.6mmol) of ferric trichloride into the three-necked flask, cool to 20°C, and dropwise add 7.15g of hydrogen peroxide (10%, 21mmol) , the dropping time is 2 hours; after the dropwise addition, keep warm for 1 hour, add 50ml of water and 50ml of ethyl acetate, separate the liquids, extract the aqueous phase twice with 30ml of ethyl acetate, combine the organic phases, wash with 30ml of water three times, no Dry over sodium sulfate, concentrate under reduced pressure in vacuo to obtain 7.06 g of a light yellow solid, as determined by HPLC: the content of prothioconazole is 93.2%, the content of impurity B is 0.6%, and the yield is 95.4%.

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Abstract

The invention relates to a synthetic method of prothioconazole. The method specifically comprises the following steps: oxidizing an intermediate A by ferric chloride to generate prothioconazole and simultaneously generate ferrous chloride and hydrogen chloride, oxidizing the ferrous chloride and the hydrogen chloride by hydrogen peroxide dropwise added into the system to regenerate ferric chloride, continuing to oxidize the intermediate A by the generated ferric trichloride to obtain prothioconazole, and repeating the steps until the intermediate A is completely converted into the prothioconazole. According to the synthesis method of prothioconazole, only a catalytic amount of ferric chloride is needed, a byproduct is water, a large amount of three wastes generated by a traditional ferricchloride oxidation method are avoided, and a mild oxidant ferric chloride is adopted, so that desulfurization impurities are greatly reduced, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of synthesis of novel broad-spectrum triazolethione fungicides, and in particular relates to a synthesis method of prothioconazole. Background technique [0002] Prothioconazole is a triazolethione fungicide discovered, developed and produced by Bayer. It is mainly used to prevent and control many diseases of cereals, wheat, beans and other crops. It is one of the important fungicides. [0003] The synthesis of prothioconazole mainly adopts the hydrazine hydrate method and the triazole method (such as patent CN1058712B). Due to the harsh process conditions, low yield and relatively poor product quality of the triazole method, the hydrazine hydrate method is widely used at home and abroad. method. In the hydrazine hydrate method of the patent CN1137103C, the last step is to oxidize the heterocyclic compound A and ferric chloride to obtain prothioconazole, and simultaneously produce ferrous chloride and hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 汪静莉李新良陈晓龙王大文李大娟
Owner JIANGYIN SULI CHEM
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