Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Chiral isoxadifen-ethyl compound and preparation method and application thereof

A technology of ethyl isoxadifen and ethyl stilbene ketonate, which is applied in the field of ethyl isoxadifen, can solve the problems of unfavorable industrial application, waste, and low product yield, and achieve outstanding results Substantial characteristics, mild reaction conditions, and the effect of reducing environmental pollution

Active Publication Date: 2018-02-02
ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
View PDF2 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In method one, a large amount of 1,1-stilbene needs to be wasted, which makes the cost of preparing ethyl isoxadifen in this method too high and is not suitable for industrial production; in method two, triethylamine is used as organic base, and some by-products Formation, the product yield is lower; Though method three can improve the yield of reaction, the cost of reactant is too high, is unfavorable for industrial application
Simultaneously, none of these preparation processes has studied the structure of isoxadifen ethyl ester, and can not obtain highly active single-configuration isoxadifen ethyl ester product

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Chiral isoxadifen-ethyl compound and preparation method and application thereof
  • Chiral isoxadifen-ethyl compound and preparation method and application thereof
  • Chiral isoxadifen-ethyl compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Such as figure 1 As shown, this embodiment provides a preparation method of chiral isoxadifen ethyl ester compound, which comprises the following steps:

[0032] The cross-aldol condensation reaction first weighs benzophenone and ethyl pyruvate according to the molar ratio of 1.2:1.0, and then takes the benzophenone and the ethyl pyruvate mass sum of 3 times the mass of the hydroxide sodium solution, adding the benzophenone into the sodium hydroxide solution, then dropwise adding the ethyl pyruvate, reacting at 50-90°C for 3 hours, then removing the solvent, and recrystallizing with 60% ethanol solution, Filtrate to obtain ethyl distyrene ketoacetate;

[0033] Oximation reaction Mix the ethyl distyrene ketovate and hydroxylamine hydrochloride uniformly according to the molar ratio of 1:0.8, react at 50-70°C for 0.3-0.8h, then react at room temperature for 0.2-0.7h, and filter , dry treatment, obtain ethyl distyryl formate ketone oxime;

[0034] Addition and ring clos...

Embodiment 2

[0037] Such as figure 1 As shown, this embodiment provides a preparation method of chiral isoxadifen ethyl ester compound, which comprises the following steps:

[0038] The cross-aldol condensation reaction first weighs benzophenone and ethyl pyruvate according to the molar ratio of 1.5:1.0, and then takes 5 times the mass sum of the benzophenone and ethyl pyruvate. Potassium solution, add the benzophenone into the sodium hydroxide solution, then drop into the ethyl pyruvate, react at 50-90°C for 3h, then remove the solvent, recrystallize with 70% ethanol solution, Filtrate to obtain ethyl distyrene ketoacetate;

[0039] The oximation reaction mixes the ethyl distyrene ketovate and hydroxylamine hydrochloride uniformly according to the molar ratio of 1:1.2, reacts at 50-70°C for 0.3-0.8h, and then reacts at room temperature for 0.2-0.7h, After filtration and drying treatment, ethyl distyryl formate ketone oxime was obtained;

[0040] Addition and ring closure reaction Mix t...

Embodiment 3

[0043] Such as figure 1 As shown, this embodiment provides a preparation method of chiral isoxadifen ethyl ester compound, which comprises the following steps:

[0044]The cross-aldol condensation reaction first weighs benzophenone and ethyl pyruvate according to the molar ratio of 1.3:1.0, and then takes 4 times the mass sum of the benzophenone and ethyl pyruvate. sodium solution, adding the benzophenone into the sodium hydroxide solution, then dropwise adding the ethyl pyruvate, reacting at 50-90°C for 3 hours, then removing the solvent, and recrystallizing with 80% ethanol solution, Filtrate to obtain ethyl distyrene ketoacetate;

[0045] The oximation reaction mixes the ethyl distyrene ketovate and hydroxylamine hydrochloride uniformly according to the molar ratio of 1:1.1, reacts at 50-70°C for 0.3-0.8h, and then reacts at room temperature for 0.2-0.7h, After filtration and drying treatment, ethyl distyryl formate ketone oxime was obtained;

[0046] Addition and ring c...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of a chiral isoxadifen-ethyl compound. The compound prepared by the method is a single enantiomer. The preparation method is simple, few in byproduct, highin product yield and wide in application prospect. In addition, the invention further provides a herbicide safener. The herbicide safener contains the chiral isoxadifen-ethyl compound serving as an active ingredient, so that application range of herbicide can be expanded effectively.

Description

technical field [0001] The present invention relates to ethyl isoxadifen compound, in particular to a chiral ethyl isoxadifen compound and a preparation method thereof. In addition, the present invention also relates to ethyl isoxadifen compound used in weed control application of safeners. Background technique [0002] Isoxadifen is a commonly used herbicide safener, which can reduce or eliminate the phytotoxicity of herbicides to crops. About the synthesis of isoxadifen ethyl ester, mainly contain following several methods at present: [0003] Method 1: Dissolve 1,1-stilbene and triethylamine in ether at 0°C, add ethyl 2-chloro-2-oximinoacetate dissolved in ether dropwise, and continue stirring at room temperature After one hour, water was added, and then the mixture was extracted with diethyl ether. After drying over magnesium sulfate, the diethyl ether was distilled off, and the residue was purified on a silica gel column to obtain the product; Slowly add the mixture ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/04A01N25/32A01P13/00
Inventor 邓照西王利娜杨莉娜
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com