Method for preparing pymetrozine

A technology of pymetrozine and pyridine, which is applied in the field of preparation of pymetrozine, can solve the problems of high toxicity of phosgene or solid phosgene, difficulty in monitoring the reaction, and low atom economy, and achieve easy recycling and low production cost , The effect of high atom economy

Active Publication Date: 2018-10-26
广东立威化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 1) The phosgene or solid phosgene used in the cyclization step is highly toxic and expensive, and requires high equipment requirements, and the production of a large amount of industrial waste gas such as hydrochloric acid gas will cause serious environmental pollution
[0011] 2) The route intermediate has no ultraviolet absorption under 254nm ultraviolet light, and it is not easy to monitor the progress of the reaction by simple TLC technology
[0012] 3) The reaction route goes through the process of protection and deprotection, and the atom economy is low
[0013] All in all, the synthesis process has no obvious advantages in terms of raw material cost, process operation simplicity and environmental protection.

Method used

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  • Method for preparing pymetrozine
  • Method for preparing pymetrozine
  • Method for preparing pymetrozine

Examples

Experimental program
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Effect test

Embodiment 1

[0052] 1) In a 2000mL reaction flask, install a stirrer, a thermometer, a constant pressure dropping funnel and a condenser. Add 540 mL of dimethyl carbonate at room temperature, start stirring, add 480 mL of 80% hydrazine hydrate, react at 70°C for 4 hours, stop the reaction, recover unreacted dimethyl carbonate, methanol and water by distillation under reduced pressure, and add 80% hydrazine hydrate 960mL, continued to react at 80°C for 4h, cooled to room temperature, stirred, a large amount of white solid precipitated, filtered with suction to obtain a white solid, rinsed with a small amount of methanol (100mL×3), dried to obtain 450g white solid, yield 83 %, melting point 153-155°C.

[0053]2) In a 2000mL reaction bottle, install a stirrer, a thermometer, and a constant pressure dropping funnel, add 500mL of pure water at room temperature, start stirring, slowly add 450g of carbazide, stir to dissolve, cool down to 0-5°C, and add dropwise Nicotinic aldehyde 540g, temperat...

Embodiment 2

[0057] 1) In a 2000mL reaction flask, install a stirrer, a thermometer, a constant pressure dropping funnel and a condenser. Add 540 mL of dimethyl carbonate at room temperature, start stirring, add 1000 mL of hydrazine-containing methanol solution (hydrazine accounts for 60% of the solution), stop the reaction after reflux reaction at 70°C for 4 hours, and recover unreacted dicarbonate by distillation under reduced pressure. Methyl ester, methanol, add 650mL of methanol solution containing hydrazine to the residue, continue to reflux vigorously at 80°C for 4h, cool to room temperature, stir, a large amount of white solid precipitates, filter with suction to obtain white solid with a small amount of methanol (100mL× 3) Rinse and dry to obtain 460 g of white solid with a yield of 85% and a melting point of 152-154°C.

[0058] 2) In a 2000mL reaction bottle, install a stirrer, a thermometer, and a constant pressure dropping funnel, add 500mL of ethanol at room temperature, start...

Embodiment 3

[0062] 1) In a 2000mL reaction flask, install a stirrer, a thermometer, a constant pressure dropping funnel and a condenser. Add 540 mL of dimethyl carbonate at room temperature, start stirring, add 480 mL of ethanol solution of hydrazine (hydrazine accounts for 80% of the solution by volume), stop the reaction after reacting at 70°C for 4 hours, and recover unreacted dimethyl carbonate by distillation under reduced pressure , methanol and ethanol, add 540mL of ethanol solution of hydrazine to the residue, continue to react at 80°C for 4h, cool to room temperature, stir, a large amount of white solid precipitates, filter with suction, and rinse the white solid with a small amount of methanol (100mL×3) After washing and drying, 455 g of white solid was obtained, the yield was 84%, and the melting point was 154-156°C.

[0063] 2) In a 2000mL reaction flask, install a stirrer, a thermometer, and a constant pressure dropping funnel, add 500mL of isopropanol at room temperature, st...

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Abstract

The invention discloses a method for preparing pymetrozine with an aim to provide a synthesis method short in reaction route of the pymetrozine, small in environmental pollution and simple in technology operation, and belongs to the technical field of organic synthesis. The method includes the steps of 1), allowing dimethyl carbonate serving as a raw material to be subjected to hydrazinolysis withhydrazine hydrate to obtain carbazide; 2), subjecting carbazide and smoke aldehyde to condensation reaction to obtain (E)-N'-(pyridine-3-kiya methyl) hydrazine carbon hydrazide; 3), subjecting (E)-N'-( pyridine-3-kiya methyl) hydrazine carbon hydrazide and chloroacetone to condensation reaction to obtain (E)-N'-(Z)-1-chloropropyl-2-subunit)-2-(pyridine-3-kiya methyl) diazanyl-1-carbohydrazide; 4), subjecting (E)-N'-(Z)-1-chloropropyl-2-subunit)-2-(pyridine-3-kiya methyl) diazanyl-1-carbohydrazide to ring formation under the alkaline condition to obtain the pymetrozine.

Description

technical field [0001] The invention discloses a preparation method of pymetrozine, which belongs to the field of organic synthesis. Background technique [0002] Pymetrozine (Pymetrozine) belongs to pyridine or triazinone insecticides, is a brand-new non-biocide insecticide, was first developed by Ciba-Geigy in 1988, and this product is effective on the piercing and sucking mouth of various crops. showed excellent control effect on organ pests. Pymetrozine has a contact effect on pests and also has systemic activity. Studies using electropenetrography (EPG) technology have shown that no matter in drip, feeding or injection experiments, as long as aphids or planthoppers come into contact with pymetrozine, they will almost immediately produce a stylet blocking effect, stop feeding immediately, and eventually starve to death , and this process is irreversible. Therefore, pymetrozine has an excellent function of blocking insect transmission. Its main features are as follows...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 董钢叶炎婵杨金珠方岩雄
Owner 广东立威化工有限公司
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