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A kind of enantiomeric mixture and its preparation method and application

A mixture and enantiomer technology, applied in the field of enantiomer mixture and its preparation, can solve the problems of low drug efficacy and high application amount, achieve the effects of small environmental impact, mild reaction conditions, and reduce pesticide application amount

Active Publication Date: 2021-11-23
DALIAN CHEMPHY CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, benzamid, which is used in agriculture, is its racemate compound, but there are problems of low drug efficacy and high application amount

Method used

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  • A kind of enantiomeric mixture and its preparation method and application
  • A kind of enantiomeric mixture and its preparation method and application
  • A kind of enantiomeric mixture and its preparation method and application

Examples

Experimental program
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Effect test

preparation example Construction

[0039] The present invention also provides a method for preparing the enantiomeric mixture described in the above technical scheme, comprising the following steps:

[0040] Esterifying isovaline with methanol in the presence of thionyl chloride to obtain isovaline methyl ester hydrochloride, the isovaline being L-isovaline or D-isovaline ;

[0041] The isovaline methyl ester hydrochloride is subjected to amidation reaction with 3,5-dichloro-4-methylbenzoyl chloride in a buffer solution to obtain 2-(3,5-dichloro-4-methyl Methylbenzoyl)-2-methylbutyrate;

[0042] The 2-(3,5-dichloro-4-methylbenzoyl)-2-methylbutanoic acid methyl ester is subjected to a cyclization reaction to obtain 2-(3,5-dichloro-4-methyl Phenyl)-4-ethyl-4-methyloxazol-5(4H)-one;

[0043] The 2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyloxazol-5(4H)-one and methyl Wittig reagent were carried out under alkaline conditions Wittig reaction to obtain 2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyl-5-methyle...

Embodiment 1

[0085] Embodiment 1: the preparation of S-benzamid

[0086] (1) Esterification reaction:

[0087] Suspend 117 g (1 mol) of L-isovaline in 1,500 mL of methanol, and slowly add 179 g (1.5 mol) of thionyl chloride to the suspension with sufficient stirring. After the addition, the temperature was raised to reflux for 3h. The resulting reaction mixture was cooled to room temperature and filtered. The filter cake was washed several times with methanol. The filtrate and methanol washings were combined and concentrated under reduced pressure. Toluene was added to the obtained residue, followed by stirring. Toluene was removed to obtain 159 g of the expected product L-isovaline methyl ester hydrochloride (yield 95%).

[0088] (2) Amidation reaction:

[0089] A. Inorganic acid-binding agent method:

[0090] Add an aqueous solution of sodium bicarbonate prepared from 13.25 g of sodium bicarbonate and 100 mL of water, and 200 mL of solvent methyl isobutyl ketone into the reactor. ...

Embodiment 2

[0104] Embodiment 2: the preparation of R-benzamid

[0105] (1) Esterification reaction:

[0106] 117 g (1 mol) of D-isovaline was suspended in 1500 mL of methanol. Under thorough stirring, 179 g (1.5 mol) of thionyl chloride was slowly added to the suspension. After the addition, the temperature was raised to reflux for 3h. The resulting reaction mixture was cooled to room temperature and filtered. The filter cake was washed several times with methanol. The filtrate and methanol washings were combined and concentrated under reduced pressure. Toluene was added to the obtained residue, followed by stirring. The toluene was removed to obtain 156 g of the expected product D-isovaline methyl ester hydrochloride (yield 93%).

[0107] (2) Amidation reaction:

[0108] With L-isovaline methyl ester hydrochloride 140g (0.83mol) and 3,5-dichloro-4-methylbenzoyl chloride 190.5g (0.853mol) and methyl isobutyl ketone that were made in the previous step Add each 1.0 L dropwise to th...

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Abstract

The invention provides a mixture of enantiomers and its preparation method and application, belonging to the technical fields of pesticide chemistry and organic synthesis. In the present invention, the mixture of enantiomers is a mixture of S-benzamid and R-benzamid, and the purity of the enantiomers is high. According to the pesticide pharmacological effect of benzamid, rational use and targeting at different species In order to improve the bactericidal efficacy of benzamid, and at the same time effectively reduce the amount of pesticide application of benzamid, and reduce Possible risks of environmental pollution and reduction of pesticide residues in crops and fields.

Description

technical field [0001] The invention relates to the technical fields of pesticide chemistry and organic synthesis, in particular to a mixture of enantiomers and its preparation method and application. Background technique [0002] Zoxamide is a microtubule aggregation inhibitor developed and listed by Rohm HaaS in 2001 for the prevention and treatment of oomycete pathogenic microorganisms. Has the following chemical structure: [0003] [0004] This compound belongs to a class of benzamide compounds, and its mechanism of action is to inhibit the aggregation of microtubules in pathogenic bacteria cells. Good bactericidal effect. Benhexamid has a wider range of activity than other compounds, and has effects on cells including oomycetes and non-oomycetes fungi, protozoa, plants and mammals, and its strength varies with different types of organisms . At the cellular level, the role of such benzamide compounds is to prevent the division of the nucleus and destroy the cytos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/76C07C231/10A01P3/00
Inventor 赵宏徐海珍
Owner DALIAN CHEMPHY CHEM
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