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Azoxystrobin synthesis method

A synthetic method, the technology of azoxystrobin, which is applied in the field of fungicide synthesis, can solve the problems of copper salts and tertiary amines with weak catalytic ability, decreased reaction rate, and sensitive reaction temperature, etc., and achieve simple reaction, improved safety, and high reaction rate. The effect of mild conditions

Active Publication Date: 2015-10-14
CHONGQING UNISPLENDOUR CHEM
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Problems solved by technology

But there is following shortcoming in above-mentioned technology: the reaction of compound shown in formula (3) and 4,6-dichloropyrimidine is also an exothermic process, and this reaction process is very sensitive to reaction temperature, and when temperature is low, rate of reaction descends significantly, When the temperature is high, the disubstituted products shown in formulas (6), (7) and (8) will be produced
[0020] The shortcoming of this method is that (E)-2-(2-hydroxyphenyl)-3-methoxymethyl acrylate is difficult to prepare; Use high-boiling point solvent, reaction is carried out at high temperature, energy consumption is high; Reaction needs inert gas Under protection; copper salt and tertiary amine have weak catalytic ability

Method used

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Effect test

Embodiment 1

[0054] (1) Add 3-(α-methoxy)-methylenebenzofuran-2(3H)-one 179.6g (98%, 1.0mol) and 400mL methanol into a 1000mL four-neck flask, stir well and cool To -5-0°C, add 198g sodium methoxide methanol solution (30%, 1.1mol) dropwise at this temperature, continue to keep warm for 1h after the dropwise addition, sample analysis, 3-(α-methoxy)-methylene Benzofuran-2(3H)-one remained at 0.13%, and the reaction solution was neutralized by adding acetic acid (6.7g, 99%, 0.11mol) and kept at room temperature for use.

[0055] (2) Put 126g (95%, 1mol) of salicylonitrile solid, 60g (99%, 0.56mol) of sodium carbonate, and 500mL of toluene into a 2000mL reaction flask, heat and reflux for dehydration, cool to room temperature after dehydration, and then add 152g (98%, 1mol) of 4,6-dichloropyrimidine, reacted at room temperature, took a sample for 4 hours, HPLC analysis showed that the content of 4-chloro-6-(2-cyanophenoxy)pyrimidine was 96.7%, 4,6-dichloropyrimidine The content of pyrimidine ...

Embodiment 2

[0058] (1) Add 3-(α-methoxy)-methylenebenzofuran-2(3H)-one 179.6g (98%, 1.0mol) and 400mL methanol into a 1000mL four-neck flask, stir well and cool To -5-0°C, add 198g sodium methoxide methanol solution (30%, 1.1mol) dropwise at this temperature, continue to keep warm for 1h after the dropwise addition, sample analysis, 3-(α-methoxy)-methylene Benzofuran-2(3H)-one remained at 0.28%, and the reaction solution was neutralized by adding acetic acid (6.7g, 99%, 0.11mol) and kept at room temperature for use.

[0059] (2) Put 126g (95%, 1mol) of salicylonitrile solid into a 2000mL reaction flask, 60g (99%, 0.56mol) of sodium carbonate, 500mL of 4-methyl-2-pentanone, heat and reflux for dehydration, anhydrous After removal, cool to room temperature, then add 152g (98%, 1mol) of 4,6-dichloropyrimidine, react at room temperature, take samples for 4h, HPLC analysis shows that the content of 4-chloro-6-(2-cyanophenoxy)pyrimidine is 97.5 %, the content of 4,6-dichloropyrimidine is less ...

Embodiment 3

[0062] (1) Add 3-(α-methoxy)-methylenebenzofuran-2(3H)-one 179.6g (98%, 1.0mol) and 400mL methanol into a 1000mL four-neck flask, stir well and cool To -5-0°C, add 198g sodium methoxide methanol solution (30%, 1.1mol) dropwise at this temperature, continue to keep warm for 1h after the dropwise addition, sample analysis, 3-(α-methoxy)-methylene Benzofuran-2(3H)-one remained at 0.05%, and the reaction solution was neutralized by adding acetic anhydride (6.2 g, 99%, 0.06 mol) and kept at room temperature for use.

[0063] (2) Put 152g (98%, 1mol) of 4,6-dichloropyrimidine and 750mL of N,N-dimethylformamide into a 2000mL reaction flask, and add 148.5g (95%, 1mol) of sodium salicylonitrile solid in batches. 1mol), reacted at room temperature for 4 hours and took samples. HPLC analysis showed that the content of 4-chloro-6-(2-cyanophenoxy)pyrimidine was 96.5%, and the content of 4,6-dichloropyrimidine was less than 1%. The reaction solution was set aside.

[0064] (3) Add 3.5 g of...

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Abstract

The invention discloses an azoxystrobin synthesis method. The method is characterized in the steps of a, 3-(alpha-methoxy)-methylenebenzofuran-2(3H)-one and excessive sodium methoxide are subjected to a reaction; an organic acid or organic acid anhydride is added for neutralizing excessive sodium methoxide; and a reaction liquid is obtained; b, under an alkaline condition, 4,6-dichloropyridine is subjected to a coupling reaction with 2-hydroxybenzonitrile or a salt thereof, and a reaction liquid is obtained; c, the reaction liquid obtained in the step b is subjected to a reaction with the reaction liquid obtained in the step a under the existence of a catalyst; desalination is carried out when the reaction is finished, metal chloride is added, and a reaction is carried out under heating; and post-treatment is carried out, such that azoxystrobin is obtained. The method has mild reaction conditions. According to method, the production of a byproduct 4-chloro-6-methoxy pyrimidine caused by the reaction of the excessive sodium methoxide and 4,6-dichloropyrimidine in a traditional method can be avoided, and the production of disubstituted products can be avoided. An olefination reaction can be carried out under normal pressure or negative pressure, and highly toxic catalysts such as dimethyl sulfate are not used in the reaction process, such that safety is greatly improved, and environment pollution is greatly reduced. The reaction is pure, and less byproducts are produced.

Description

technical field [0001] The invention relates to a method for synthesizing a fungicide, in particular to a method for synthesizing azoxystrobin. Background technique [0002] Azoxystrobin is a methoxyacrylate fungicide with the chemical name (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl] - Methyl 3-methoxyacrylate. The fungicide is broad-spectrum and highly effective, and has good activity against almost all fungal diseases such as powdery mildew, rust, glume blight, net spot, downy mildew, and rice blast. Azoxystrobin is the most widely used fungicide in the world. A large number of patent documents disclose its synthesis method. At present, there are three main routes for the synthesis of azoxystrobin: [0003] Route 1: Synthesis of azoxystrobin from methyl (E)-2-[2-(6-pyrimidin-4-yloxy)phenyl]-3-methoxyacrylate and salicylonitrile or its salt. [0004] [0005] A kind of synthetic method of azoxystrobin is disclosed in WO9208703, the method will (E)-2-[2-(6-ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52B01J27/10B01J27/125B01J27/135B01J27/128A01P3/00
CPCB01J27/10B01J27/125B01J27/128B01J27/135C07D239/52
Inventor 丁永良刘佳张飞游欢何咏梅
Owner CHONGQING UNISPLENDOUR CHEM
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