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A kind of preparation method of highly active myclobutanil

A technology of myclobutanil and high activity is applied in the field of preparation of high-activity myclobutanil, which can solve the problems of complex splitting, achieve high yield and purity, reduce by-products, and avoid the effects of cyano hydrolysis

Active Publication Date: 2018-05-15
浙江大鹏药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although, as Chinese patent literature (publication number: CN106674139A) discloses a kind of preparation method of myclobutanil stereoisomer, the enantiomer of myclobutanil is resolved by adopting the method of simulated moving bed, although, its Highly active S-myclobutanil can be obtained through resolution, but it is only after the synthesis of the racemic mixture of myclobutanazole, followed by subsequent resolution, the resolution is too complicated
And at present, there is no report on the market that obtains a high content of highly active S-myclobutanil directly in the synthesis process

Method used

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  • A kind of preparation method of highly active myclobutanil
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  • A kind of preparation method of highly active myclobutanil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The highly active solid base catalyst used in the following examples can be prepared according to the following methods:

[0038] Select according to the ratio of each raw material in the high activity solid catalyst, take 100g gamma-Al 2 o 3 As a carrier, add 2g of aluminum sol as a binder, and then add 15g of magnesium acetate (Mg(OAc) 2 ), after mixing and grinding for 1 hour, add 10 calcium hydroxide and 1g inorganic base, the inorganic base is alkali metal hydroxide, wherein the inorganic base can be sodium hydroxide or potassium hydroxide, then add 3g polyacrylamide as extrusion aid Agent, the molecular weight is between 11 million and 13 million, mixed and ground for 2 hours, added 20g of water, extruded into strips, dried, and finally placed in a muffle furnace and roasted at 500°C-600°C. Carry out calcining treatment 4 hours in the embodiment, obtain the composite solid base catalyst of high activity, standby.

Embodiment 2

[0040] The dimethyl sulfoxide solution of potassium triazole used in the following examples can be prepared according to the following method:

[0041] Add 80m of dimethyl sulfoxide and 25mg of toluene solvent in the reaction vessel, then add 125mg of triazole and 98mg of solid potassium hydroxide, heat, raise the temperature to reflux and carry out reflux dehydration reaction until the reaction is complete to obtain potassium triazole The dimethyl sulfoxide solution, so that the water content of the obtained potassium triazole dimethyl sulfoxide solution is less than or equal to 0.1%.

Embodiment 3

[0043] Add 300 mg of benzyl p-chloronitrile, 1500 mg of organic solvent toluene, 410 mg of bromo-n-butane, and 30 mg of highly active solid base catalyst into the three-necked flask of the reaction vessel, and raise the temperature. Then, the temperature was raised to 50°C ± 2°C for another three hours of reaction. After the reaction was completed, the temperature was slowly lowered to room temperature, filtered, and the solids were filtered off. The filtrate was collected and rectified under reduced pressure to remove the solvent to obtain intermediate 2-( 4-Chlorophenyl) hexonitrile, the yield is 91%, and the content reaches more than 99%.

[0044] Add the intermediate 2-(4-chlorophenyl) hexonitrile 300mg, chiral quaternary ammonium salt phase-transfer catalyst cinchonidine 3mg and methylene chloride 250mg obtained above in another three-necked flask of reaction vessel again, the added here Dichloromethane can be used both as a reaction raw material and as a reaction solvent...

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Abstract

The invention relates to a preparation method of high activity myclobutanil, and belongs to the technical field of pesticide synthesis. In order to solve the existing problem of low activity of nitrile bacteria due to the difficulty of splitting, the preparation method of high activity myclobutanil is provided. The method includes the steps that compound 2 (4-chlorphenyl) hexanenitrile in formula I is added into a dichloromethane solvent under the action of chiral quaternary ammonium salt phase transfer catalyst, inorganic alkali water solution is added under the condition that the temperature is controlled to be 20 DEG C to 30 DEG C, the temperature is raised to 60 DEG C to 80 DEG C, after reaction, S-1-chlorine-2-nitrile base-2-(4-N-chlorophenyl) hexane is obtained; the chiral quaternary ammonium salt phase transfer catalyst is selected from cinchonidine and / or quinine, and the compound in formula II reacts with the dimethyl sulfoxide solution of anhydrous triazole potassium, and the high activity product-type compound in formula III S-type myclobutanil is obtained. The high acitivity reactive S-myclobutanil element in the product is significantly increased, the hydrolysis of cyanide is avoided, and the effects of higher yield and purity are achieved.

Description

technical field [0001] The invention relates to a preparation method of highly active myclobutanil, which belongs to the technical field of pesticide synthesis. Background technique [0002] Myclobutanil is a class of triazole fungicides with protective and therapeutic activity. It mainly inhibits the biosynthesis of ergosterol of pathogenic bacteria. It has the advantages of systemic absorption and high efficiency and broad spectrum. It has excellent effects on the prevention and treatment of various fungi. activity. [0003] For the synthetic technique of myclobutanil, generally adopt three-step reaction at present: at first take p-Chloronitrile, n-butane chloride and tetrapropylammonium bromide (triethylamine) as raw materials, control a certain temperature and drop 50 % of liquid caustic soda to obtain 2-(4-chlorophenyl) hexonitrile; ) into the reaction kettle to obtain 1-chloro-2-cyano-2-(4-chlorophenyl) hexane; put dimethyl sulfoxide, sodium hydroxide solution with a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08C07C255/35C07C253/30
CPCC07B2200/07C07C253/30C07D249/08C07C255/35
Inventor 徐学春徐大国杜青峰王辉王自田
Owner 浙江大鹏药业股份有限公司
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