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Enantiomer mixture and preparation method and application thereof

A technology of enantiomers and mixtures, applied in the field of enantiomer mixtures and their preparation, can solve the problems of high dosage and low drug efficacy, and achieve the effects of small environmental impact, mild reaction conditions, and safe and reliable process

Active Publication Date: 2019-05-28
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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  • Enantiomer mixture and preparation method and application thereof
  • Enantiomer mixture and preparation method and application thereof
  • Enantiomer mixture and preparation method and application thereof

Examples

Experimental program
Comparison scheme
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 an enantiomer mixture and a preparation method and application thereof, and belongs to the technical field of pesticide chemistry and organic synthesis. The enantiomer mixture is a mixture of S-zoxamide and R-zoxamide, and the enantiomer is high in purity, according to the pesticide pharmacological effects of zoxamide, the rational use is carried out, the enantiomer mixtureis prepared by zoxamide optical isomers in proportion aiming at the crops of different species and diseases conditions of the crops to increase the bactericidal efficacy of zoxamide, meanwhile, the pesticide application amount of zoxamide can be effectively reduced, possible risks of environmental pollution is reduced, and the pesticide residue amount in the crops and farmland is reduced.

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 Applications(China)
IPC IPC(8): C07C233/76C07C231/10A01P3/00
Inventor 赵宏马建华徐海珍
Owner DALIAN CHEMPHY CHEM
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