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Method for synthesizing thiacloprid amide by using thiacloprid

A technology for thiacloprid amide and amide synthesis, which is applied in the field of organic synthesis, can solve the problems of difficulty in extraction, low total yield, low concentration of added substrate and the like, and achieves the effects of simple process, fast reaction and low cost

Inactive Publication Date: 2010-08-04
NANJING INST OF ENVIRONMENTAL SCI MINIST OF ECOLOGY & ENVIRONMENT OF THE PEOPLES REPUBLIC OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies on the soil environmental behavior of thiacloprid show that the main metabolic pathway of this compound in soil is to hydrolyze the cyanoimine pharmacophore to generate thiacloprid amide, the conversion rate of which is as high as 70%, and the amide The half-life of thiacloprid in soil is as high as 100 days or more (Khron 2001), which may cause secondary pollution of soil
Although thiacloprid can be synthesized from thiacloprid by soil degradation method, the price of pure thiacloprid on the market is as high as 20,000 yuan / gram
Directly using chemical hydrolysis to synthesize thiacloprid amides from thiacloprid has not been reported at home and abroad.

Method used

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  • Method for synthesizing thiacloprid amide by using thiacloprid
  • Method for synthesizing thiacloprid amide by using thiacloprid
  • Method for synthesizing thiacloprid amide by using thiacloprid

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Weigh 3.0g of thiacloprid (purity is 95%) and place it in a 100ml beaker, add 30ml of acetone to dissolve, add 10ml of concentrated sulfuric acid, seal the beaker with plastic wrap, heat to 70°C with an electromagnetic oven, react for 2 hours, and cool The reaction solution has a product yield of 89%. After adding 10% mass ratio of sodium hydroxide to adjust the pH to 7.0, 50 ml of double distilled water was added to completely dissolve the reaction product, and 200 ml of ethyl acetate was added for extraction twice. After the extract was left to stand and separated, the ethyl acetate phase was collected, and about 20 g of anhydrous sodium sulfate was added to absorb the moisture. The ethyl acetate phase is concentrated and crystallized in a vacuum concentration crystallizer, and the crystals are redissolved in ethyl acetate. After vacuum drying, the crystals are washed with acetonitrile to remove the substrate thiacloprid, and 10 ml of acetonitrile is added each time. ...

Embodiment 2

[0020] Take by weighing 6.0g of thiacloprid and place it in a 1000ml beaker, add 100ml of acetone to dissolve, add 50ml of sulfuric acid with a mass ratio of 10%, seal the beaker with plastic wrap, stir with a magnetic stirrer and keep the reaction temperature at 30°C, Add 20ml of 10% sulfuric acid in 3 hours, and react for 20 hours in total. Adding sulfuric acid step by step can reduce the generation of by-products, and the product generation rate can be increased to 60%. Add 10% NaOH to adjust the pH to 7.0, remove the acetone by distillation under reduced pressure in the reaction solution and rotary evaporator, then add 10% (V / V) dichloromethane, oscillate, stand still, add 500ml ethyl acetate to the water phase for extraction twice. After the extract was left to stand and separated, the ethyl acetate phase was collected, and about 50 g of anhydrous sodium sulfate was added to absorb the moisture. The ethyl acetate phase was concentrated and crystallized in a vacuum conce...

Embodiment 3

[0022] Weigh 4.0g of thiacloprid original drug into a 1000ml beaker, add 50ml of acetone to dissolve, add 20ml of concentrated sulfuric acid, seal the beaker with plastic wrap, stir with a magnetic stirrer, heat to 100°C, add 20ml of concentrated sulfuric acid after 1 hour , stop the reaction after continuing the reaction for 1 hour. After the reaction liquid was cooled, 10% KOH was added to adjust the pH to 7.0, and double-distilled water was added until the product was completely dissolved. After the reaction liquid was distilled off under reduced pressure in a rotary evaporator to remove acetone, 500 ml of ethyl acetate was added for extraction twice. After the extract was left to stand and separated, the ethyl acetate phase was collected, and about 40 g of anhydrous sodium sulfate was added to absorb the moisture. The ethyl acetate phase was concentrated and crystallized in a vacuum concentration crystallizer. After vacuum drying, the crystals were washed twice with 10 ml ...

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Abstract

The invention discloses a chemical synthesizing method for synthesizing thiacloprid amide by using thiacloprid. Thiacloprid is used as raw material and acetone is used as solvent medium and heated reaction is conducted jointly with sulfuric acid. After the reaction liquid is neutralized by using alkali, dichloromethane can be used first to remove unreacted bottom matters or ethyl acetate is directly used for extraction, the extracted liquid is concentrated and crystallized, the crystal is washed by using acetonitrile and the thiacloprid amide is obtained. The synthesizing method can synthesize thiacloprid amide in short time at one step and has the advantages of few by-products, simple and convenient process and high yield.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic matter, in particular to a synthesis method of neonicotinoid insecticide derivatives. Background technique [0002] Thiacloprid is another broad-spectrum nicotinic systemic insecticide developed by Bayer after imidacloprid. It has the characteristics of high efficiency, quick effect and long-lasting effect on piercing-sucking mouthparts pests and some chewing mouthparts pests, low toxicity to mammals, and environmental safety. It can prevent and control crops such as rice, vegetables, fruit trees, cotton, and potatoes. of most pests. Thiacloprid is currently used on more than 50 crops worldwide (Elbert et al.2008). Studies on the metabolism of thiacloprid in animals and plants show that thiacloprid can be hydroxylated, dehydrogenated, hydrolyzed, etc. in animals and plants, with complex metabolic pathways and diverse metabolites (Ford et a1.2006). Studies on the soil environmental ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06
Inventor 葛峰单正军张冲孔德洋
Owner NANJING INST OF ENVIRONMENTAL SCI MINIST OF ECOLOGY & ENVIRONMENT OF THE PEOPLES REPUBLIC OF CHINA
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