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Pyraclostrobin and method for economically synthesizing same

An economical technology of pyraclostrobin, applied in the field of economical synthesis of pyraclostrobin, can solve the problems of high reaction temperature, low yield, uneconomical, etc., achieve high purity, high material utilization rate, Simple operation effect

Inactive Publication Date: 2012-04-04
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

U.S. Patent (US7816392) has the report of relevant crystal form to it; Chinese patent (CN95194436.3) has the relevant report of its synthesis, but the yield is only 39%; "Pesticide Research and Application" [Agrochemicals Research & Application, 13 (2009), 16] although the crude product yield reaches 95%, the purity is low, and the reaction temperature is higher, the cost is large, and it is uneconomical

Method used

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  • Pyraclostrobin and method for economically synthesizing same
  • Pyraclostrobin and method for economically synthesizing same
  • Pyraclostrobin and method for economically synthesizing same

Examples

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Effect test

Embodiment 1

[0017] Add 78.8g (0.2mol) N-hydroxyl-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]phenylcarbamate, 450mL acetone into a 1L four-necked flask, 41.9g (0.3mol) of anhydrous sodium carbonate, stirred at room temperature (10-30°C) for 0.5 hours, added dropwise 30.6g (0.24mol) of dimethyl sulfate at 25°C, after the dropwise addition, at a temperature of 25°C React for 2 hours, wash with water to neutralize, remove the solvent, add isopropanol to immerse, cool at 0-5 ° C, stand for 1 hour to recrystallize, and suction filter to obtain 77.7g of white crystals, the content of which is determined by HPLC (external standard) is 98.1%. Yield 98.3%, mp: 65°C, 1H NMR (300MHz, CDCl 3 ): δ: 3.8 (s, 3H, OCH 3 ), 5.9 (d, 1H, -PyH), 7.2-7.7 (m, 9H, ArH).

Embodiment 2

[0019] Add 78.8g (0.2mol) N-hydroxyl-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]phenyl carbamate in 1L four-necked bottle, 1,2 - 450 mL of dichloroethane, 41.9 g (0.3 mol) of anhydrous sodium carbonate, stirred at room temperature for 0.5 hours, and added dropwise 30.6 g (0.24 mol) of dimethyl sulfate at 25°C. React for 2 hours, wash and neutralize with water, remove the solvent, add methanol or ethanol to immerse, cool at 0-5°C, let stand for 1 hour to recrystallize, and suction filter to obtain 77.2g of white crystals, the content of which was determined by HPLC (external standard) was 97.6%. The rate is 97.1%.

Embodiment 3

[0021] Add 78.8g (0.2mol) N-hydroxyl-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]phenylcarbamate to a 1L four-neck flask, 450mL butanone , 30.7g (0.22mol) of anhydrous potassium carbonate, stirred at room temperature for 0.5 hours, added dropwise 28g (0.22mol) of dimethyl sulfate at 25°C, after the dropwise addition, reacted at a temperature of 25°C for 2 hours, washed with water and neutralized , remove the solvent, add n-butanol to immerse, cool at 0-5 ° C, stand for 1 hour to recrystallize, and suction filter to obtain 77.0 g of white crystals, the content of HPLC (external standard) is 97.2%, and the yield is 96.4%.

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Abstract

The invention aims to provide pyraclostrobin and a method for economically synthesizing the same. High purity pyraclostrobin can be synthesized at low cost. The method comprises the following steps of: adding N-hydroxy-N-2-[(N-parachlorobenzyl)-3-pyrazoloxymethyl]phenyl carbamate and an acid bonding agent into a polar solvent or non-polar solvent, uniformly mixing, adding dimethyl sulfate, and reacting at the temperature of between 20 and 30DEG C; and after the reaction is monitored to be finished through high performance liquid chromatography (HPLC), adding water to neutralize until the pH=7, removing the solvent, immersing in a recrystallization solvent, performing recrystallization, and removing a recrystallization solution to obtain the pyraclostrobin, wherein a molar ratio of the N-hydroxy-N-2-[(N-parachlorobenzyl)-3-pyrazoloxymethyl]phenyl carbamate to the acid bonding agent to the dimethyl sulfate is 1:(1-1.8):(1-1.8). By the invention, the energy consumption is low, the utilization rate of materials is high, the operation is simple, and the yield and purity of the product are high; and compared with the traditional method, the method is more energy-saving, environment-friendly and economic, and has great industrial application value.

Description

technical field [0001] The invention relates to chemical industry, in particular to an economical synthesis of pyraclostrobin and a method thereof. Background technique [0002] Pyraclostrobin, also known as pyraclostrobin, is a broad-spectrum methyl methoxyacrylate fungicide with a pyrazole structure discovered by BASF in 1993. It can prevent and control plant diseases caused by almost all types of fungal pathogens such as Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes, and it is also a hormone-type fungicide. It has the characteristics of low toxicity, safety to non-target organisms, safety and friendliness to users and the environment. U.S. Patent (US7816392) has the report of relevant crystal form to it; Chinese patent (CN95194436.3) has the relevant report of its synthesis, but the yield is only 39%; "Pesticide Research and Application" [Agrochemicals Research & Application, 13 (2009), 16] Although the crude product yield reaches 95%, the purity is low, and...

Claims

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Application Information

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IPC IPC(8): C07D231/22A01N47/24A01P3/00
Inventor 刘孟奇白若飞赵伟杰
Owner HENAN UNIV OF CHINESE MEDICINE
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