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Preparation method of efficient and low-toxicity acaricide hexythiazox

A high-efficiency, low-toxic, and hexythifen technology, applied in the field of acaricides, can solve the problems of being unsuitable for industrial production, long reaction steps, cumbersome operations, etc., and achieve the effects of improving production environment, mild reaction, and reducing environmental pollution

Inactive Publication Date: 2018-09-21
JIANGSU HEBEN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route has long reaction steps, cumbersome operation, high pollution and low yield, and is not suitable for industrial production

Method used

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  • Preparation method of efficient and low-toxicity acaricide hexythiazox
  • Preparation method of efficient and low-toxicity acaricide hexythiazox
  • Preparation method of efficient and low-toxicity acaricide hexythiazox

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The preparation method of a high-efficiency and low-toxicity acaricide hexythiazox according to the present invention includes the following steps:

[0042] (1) Oximation reaction

[0043] Put 200ml of methanol, 34.06g (0.2mol) of p-chloropropiophenone, 14.46g (0.204mol) of hydroxylamine hydrochloride into a 500ml four-necked flask, raise the temperature for reflux reaction, after the reaction, cool down, add 8.08g (0.2mol) of sodium hydroxide Sum up to Ph=7, then recover methanol under reduced pressure, add 200ml of toluene and 100ml of water, stir to dissolve for 30min, stand to separate the layers, separate the water layer, the organic phase is heated and refluxed to remove the water to obtain p-chlorophenylpropoxime toluene liquid;

[0044] (2) Rearrangement reaction

[0045] Add 20.44g (0.2mol) of triethylamine to the toluene solution of p-chlorophenylpropoxime obtained from the previous oximation reaction, reduce the temperature to 5±3℃, and add 23.38g (0.2mol) of methan...

Embodiment 2

[0057] The preparation method of a high-efficiency and low-toxicity acaricide hexythiazox according to the present invention includes the following steps:

[0058] (1) Oximation reaction

[0059] Put 200ml of methanol, 34.06g (0.2mol) of p-chloropropiophenone (0.2mol), and 17.02g (0.24mol) of hydroxylamine hydrochloride into a 500ml four-necked flask. The reaction is heated and refluxed. After the reaction is completed, the temperature is lowered. Add potassium hydroxide 14.93g (0.24mol) Sum to Ph=7, then recover methanol under reduced pressure, add 200ml of toluene and 100ml of water, stir to dissolve for 30min, stand to separate the layers, separate the water layer, heat the organic phase to reflux and remove the water to obtain p-chlorophenylpropoxime toluene liquid;

[0060] (2) Rearrangement reaction

[0061] Add 22.49g (0.22mol) of triethylamine to the toluene solution of p-chlorophenylpropoxime obtained from the previous oximation reaction, reduce the temperature to 5±3℃, and ...

Embodiment 3

[0073] The preparation method of a high-efficiency and low-toxicity acaricide hethiazolone according to the present invention includes the following steps:

[0074] (1) Oximation reaction

[0075] Put 200ml of methanol, 34.06g (0.2mol) of p-chloropropiophenone, 17.02g (0.24mol) of hydroxylamine hydrochloride into a 500ml four-necked flask, raise the temperature for reflux reaction, after the reaction, cool down, add sodium hydroxide 9.79g (0.24mol) Sum to Ph=7, then recover methanol under reduced pressure, add 200ml of toluene and 100ml of water, stir to dissolve for 30min, stand to separate the layers, separate the water layer, heat the organic phase to reflux and remove the water to obtain p-chlorophenylpropoxime toluene liquid;

[0076] (2) Rearrangement reaction

[0077] Add 21.46g (0.21mol) of triethylamine to the toluene solution of p-chlorophenylpropoxime obtained from the previous oximation reaction, control the temperature to 15±3℃, and add 25.45g (0.22mol) of methanesulfony...

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Abstract

The invention discloses a preparation method of efficient and low-toxicity acaricide hexythiazox. Performing cyclization reaction on 2-amino-1-(4-chlorphenyl) propyl sulfate hydrochloride and carbon disulfide in a reaction flask under the normal-pressures alkaline condition to generate 5-(4-chlorphenyl)-methylthiazoline-2-thioketone; adding methylbenzene, the 5-(4-chlorphenyl)-methylthiazoline-2-ketone and a catalyst into the reaction flask, and dripping cyclohexyl isocyanate to perform addition reaction to obtain a hexythiazox product. By the preparation method, a cyclization technique of the 2-amino-1-(4-chlorphenyl) propyl sulfate hydrochloride and carbon disulfide under the normal-pressures alkaline condition replaces a toxic and polluted carbon oxide sulfur cyclization process, drainage of acid wastewater is greatly reduced, normal-pressure reaction replaces pressurized reaction, and industrial mass production is facilitated. According to the method, carcinogenic raw materials are omitted, toxic and lacrimatory benzyl mercaptane is avoided, production environments are improved, environmental pollution is reduced, and the content of an acquired hexythiazox original medicine is98% or more.

Description

Technical field [0001] The present invention relates to an acaricide, in particular to a preparation method of a high-efficiency and low-toxicity acaricide hexythiazox. Background technique [0002] Thiafenone, structural formula: . The odorless light yellow or white crystals of hethiazox, the pure product is anhydrous crystals, the melting point is 108-108.5℃, the vapor pressure is 0.0034mPa (20℃), the solubility in solvent (g / L) at 20℃ is: water 0.0005, chloroform 1379, xylene 362, methanol 206, acetone 160, acetonitrile 28.6, hexane 4. It is stable to heat and light, as well as acidic and alkaline media. Stable below 300°C. Degradation half-life DT in aqueous solution under sunlight 50 16.7 days. [0003] Thioxaphenone has been selling well since it was developed and put on the market by Sooda Corporation of Japan. The synthetic route of Soda Corporation of Japan is to use erythro-2-amino-1-(p-chlorophenyl)propanol hydrochloride (A) as the starting material, and then form ...

Claims

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Application Information

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IPC IPC(8): C07D277/14
CPCC07D277/14
Inventor 邓桂元陈华贾利华王成
Owner JIANGSU HEBEN BIOCHEM
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