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Preparation method of metominostrobin

A technology of phenoxystrobin and phenoxy, which is applied in oxime preparation, organic chemistry, etc., can solve the problems of operators and environmental hazards, unsuitability for industrial production, and high environmental pressure, and achieve shortened reaction time, less waste, and The effect of increasing the yield

Active Publication Date: 2014-03-12
SHANDONG KANGQIAO BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The shortcoming of this synthetic patent method is that the highly toxic compound methyl isonitrile is used in the reaction process. This compound is a gas, and the operation needs to be strictly controlled. Equipped with advanced protective equipment, not suitable for industrial production
The synthetic route is relatively long, and the highly toxic chemical sodium cyanide is used, which puts great pressure on the environment
At the same time, the intermediate product 2-(phenoxy)benzyl bromide compound of this route has increased polarity to eyes and skin

Method used

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  • Preparation method of metominostrobin
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  • Preparation method of metominostrobin

Examples

Experimental program
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Effect test

Embodiment 1

[0038] (1) Synthesis of 2-(phenoxy)benzonitrile

[0039]

[0040] In a four-necked reaction flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, add 15.5 g (0.3 mol) of ethanedinitrile and 150 ml of toluene, pour in hydrofluoric acid to saturation, and cool to the reaction temperature -20°C, add 51.0g (0.3mol) of diphenyl ether dropwise, after the dropwise addition, keep warm at this temperature for 3h, gradually rise to room temperature, stir overnight, pour the reaction mixture into 2kg of ice water, and then use 3× 150ml of dichloromethane for extraction. The organic phases were combined and concentrated to obtain phenoxybenzonitrile with a yield of 71%. The melting point is 45°C.

[0041] NMR (CDCl3) ppm: 6.92 (2H, dd), 7.11 (2H, m), 7.17 (1H, m) 7.22 (2H, m), 7.50 (1H, s), 7.77 (1H, s)

[0042] (2) Synthesis of 2-(2-phenoxybenzene)-2-oxoacetamide

[0043]

[0044] Add 240ml of 6N hydrochloric acid solution, 54g (0.24mol) of 2-(...

Embodiment 2

[0055] (1) Synthesis of 2-(phenoxy)benzonitrile

[0056]

[0057] In a four-necked reaction flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, add 34.1g (0.66mol) of ethanedinitrile and 300ml of toluene, pour in hydrofluoric acid to saturation, and cool to the reaction temperature -15°C, add 102.0g (0.6mol) diphenyl ether dropwise, after the dropwise addition, keep warm at this temperature for 3h, gradually rise to room temperature, stir overnight, pour the reaction mixture into 4Kg of ice water, and then use 3×150ml Dichloromethane extraction. The organic phases were combined and concentrated to obtain phenoxybenzonitrile with a yield of 71.5%. The melting point is 45°C.

[0058] (2) Synthesis of 2-(2-phenoxybenzene)-2-oxoacetamide

[0059]

[0060] Add 480ml of 6N hydrochloric acid solution, 108g (0.48mol) of 2-(phenoxy)benzonitrile, and 4.32g (0.24mol) of water into a 1000ml four-necked reaction flask, stir at room temperature f...

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Abstract

The invention relates to a preparation method of a pesticide active compound, in particular relates to a preparation method of metominostrobin, comprising compounding steps of acylation, hydrolyzation, oximation and methylation. Firstly, acylation is carried out by using diphenyl ether and diphenyl ether to obtain 2-(phenoxyl) benzoyl cyanide; secondly, the 2-(phenoxyl) benzoyl cyanide is hydrolyzed in an acid or alkali condition to obtain 2-(2-phenoxylbenzene)-2-oxoacetamide; thirdly, the 2-(2-phenoxylbenzene)-2-oxoacetamide reacts with hydroxylamine to obtain an oxime compound; and finally, a target product of the metominostrobin is obtained by methylating the oxime compound. According to the preparation method provided by the invention, the reaction steps and the reaction time can be shortened through an improved process, so as to improve the total yield. With the adoption of the process, the highly-toxic chemical such as carbazole or editpotassium cyanide used in the traditional process is avoided, so that the sanitary production is realized.

Description

technical field [0001] The invention relates to a preparation method of the original pesticide, in particular to a preparation method of fenoxystrobin. Background technique [0002] Phenoxystrobin [0003] Generic name: Metominostrobin; [0004] Chemical name: (E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide; [0005] Structural formula: [0006] [0007] Molecular formula: C 16 h 16 N 2 o 3 ; [0008] Molecular weight: 284.32; [0009] Melting point: 88.8°C; [0010] Vapor pressure: 1.8B×lO -5 Pa(25℃); [0011] Biological activity: sterilization; [0012] Water solubility: 0.128g / L (2O°C). [0013] Phenoxystrobin is an excellent variety of methoxyacrylate fungicides developed by Noshiogi Pharmaceutical Co., Ltd. in Japan. Because of its high efficiency, low toxicity, stable chemical properties, and wide bactericidal spectrum, it has become one of the bactericidal varieties developed by domestic and foreign pesticide companies. one. [0014] In the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/48C07C249/12
Inventor 李宁许文明陈夏玲刘瑞宾
Owner SHANDONG KANGQIAO BIO TECH CO LTD
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