Preparation method of fludioxonil

A technology of fludioxonil and methylbenzenesulfonylmethyl isonitrile, which is applied in the field of preparation of fludioxonil, can solve the problems of high cost, rare raw materials, low yield and purity, and achieve less waste and easy treatment of waste , the effect of high yield

Active Publication Date: 2022-01-11
NUTRICHEM LAB CO LTD
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Problems solved by technology

[0004] The purpose of the present invention is to overcome the problems of rare raw materials, high cost, and low yield and purity in the prior art, and to provide a method that is easy to industrialize, cheap and easy to obtain raw materials, less three wastes, high reaction yield and high purity. Obtain the preparation method of fludioxonil

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  • Preparation method of fludioxonil

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preparation example Construction

[0029] The invention provides a method for preparing fludioxonil, the method comprising: under the catalysis of the first base, 2,2-difluoro-1,3-benzodiox-4-aldehyde and cyanoacetate The step of obtaining the product after the first contact reaction through the first contact reaction, and the step of directly performing the second contact reaction with the obtained product after the first contact reaction with p-toluenesulfonylmethyl isonitrile.

[0030] According to the present invention, the product after the first contact reaction obtained by the first contact reaction is directly subjected to the second contact reaction with p-toluenesulfonylmethylisonitrile, so that the reaction can be carried out in a one-pot method. Moreover, because the preparation method of fludioxonil of the present invention has the characteristics of mild reaction conditions, high yield, less waste, and simplicity, it is very suitable for industrial production.

[0031] According to the present inv...

Embodiment 1

[0061] 5g of 2,2-difluoro-1,3-benzodiox-4-aldehyde (purity is 99% by weight, prepared according to the method in Example 2 of US5194628, the same below), catalytic amount of triethylamine and 23g Methanol is placed in the reaction bottle, and the pH is about 9.5 at this time, 2.66g methyl cyanoacetate (purity is 99% by weight) is added dropwise at room temperature for 1 hour, after the addition is completed, the reaction is stirred and reacted at room temperature for 6 hours, and the control is carried out during sampling. Finished, the normalized content of the main product was 98%, cooled to 0-5°C, added 5.3g of TosMIC (purity is 98% by weight), kept 0-10°C, added dropwise 2.1eq.21% by weight potassium hydroxide methanol solution ( 15.2g). After 1 hour of dripping, the dropwise addition is completed, the heat preservation reaction is carried out for 2 hours, the sample is controlled in the middle, and the reaction is completed, 5% by weight of dilute hydrochloric acid is add...

Embodiment 2

[0064] A trace of 21% by weight of potassium hydroxide methanol solution and 23g of methanol were placed in the reaction flask, and the pH was about 8.5 at this time, and 5g of 2,2-difluoro-1,3-benzodiox-4-aldehyde (purity of 99 % by weight), at room temperature, 2.66g methyl cyanoacetate (purity is 99% by weight) was added dropwise in 1 hour, after the dropwise addition was completed, the reaction was stirred and reacted at room temperature for 6 hours, and in the control of sampling, 0.04g methyl cyanoacetate was added, Stir the reaction for 2 hours, take a sample and control it, the reaction is completed, the normalized content of the main product is 98%, cool down to 0-5°C, add 5.3g of TosMIC (purity is 98% by weight), keep 0-10°C, add dropwise 1.8eq .21% by weight potassium hydroxide in methanol (12.9 g). After 1 hour of dripping, the dropping is completed, the reaction is kept for 2 hours, the sampling is controlled, and the reaction is completed, 5% by weight of dilute ...

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Abstract

The invention relates to the field of fungicides and discloses a preparation method of fludioxonil. The preparation method of fludioxonil of the present invention comprises: under the catalysis of the first base, carry out the first contact reaction of 2,2-difluoro-1,3-benzodiox-4-aldehyde and cyanoacetate to obtain The step of first contacting the product after the contact reaction, and the step of performing the second contact reaction with the obtained product after the first contact reaction directly with p-toluenesulfonylmethyl isonitrile. Through the above technical proposal, a preparation method for fludioxonil with high reaction yield and high purity can be provided, which is easy for industrialization, cheap and easy to obtain raw materials, less three wastes, and high in reaction yield.

Description

technical field [0001] The invention relates to the field of fungicides, in particular to a preparation method of fludioxonil. Background technique [0002] Fludioxonil is a new type of contact protection fungicide with a unique mechanism of action. It inhibits the growth of pathogenic mycelium by inhibiting the transfer related to glucose phosphorylation, and finally leads to the death of pathogenic bacteria. When applied to flowers, it mainly prevents diseases such as leaf blight, leaf spot, partial stem rot, and root rot. Fludioxonil is easy to use, can be used for foliar spraying and root irrigation, and has low dosage and low residue; it has obvious effect on pathogenic bacteria resistant to other agents; it has no systemic effect, but has strong penetrating ability. In addition, it has a remarkable control effect on root rot, stem rot and gray mold. [0003] The synthesis of fludioxonil is usually prepared by the reaction of 2,3-(difluoromethylenedioxy)cinnamonitrile...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 吴浩范胜用杨海舰
Owner NUTRICHEM LAB CO LTD
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