Second anabasine insecticide JT-L001 and chemical synthesis method thereof

A technology for pesticides and compounds, applied in the field of organic compounds, can solve the problems of complex process, high technical requirements for preparation, positive temperature effect, etc., and achieves the effects of good environmental compatibility, simple preparation process, and improved quick-acting properties.

Inactive Publication Date: 2007-08-15
JIANGSU TIANRONG GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, imidacloprid insecticides still have some shortcomings, such as the low killing activity of chewing mouthparts pests, and the broad-spectrum insecticidal properties still have certain limitations. When used at low temperature, the drug effect is affected and there is a disadvantage of positive temperature effect
In addition, the production process of imidacloprid is relatively complicated, especially the preparation of its intermediate 2-chloro-5-chloromethylpyridine requires high technical requirements, complicated process and high cost

Method used

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  • Second anabasine insecticide JT-L001 and chemical synthesis method thereof
  • Second anabasine insecticide JT-L001 and chemical synthesis method thereof
  • Second anabasine insecticide JT-L001 and chemical synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Add 100ml of absolute ethanol and 0.5g of CsCl to a 500ml reaction flask, stir and add 45.65g (0.55mol) of pure N-cyanoacetamidine, and then slowly add 84g (0.5mol) of pure 2-chloro - Mixed solution of 5-chloromethylthiazole and 50ml of absolute ethanol, keep it dropwise at room temperature for 1 hour, continue to stir for 15 minutes after the dropwise addition, raise the temperature to 70-75°C for half an hour, and discharge non-condensable gas at the same time, Then heat up to reflux, react for 1 hour, slowly cool to <10°C, precipitate crystals, filter and wash the filter cake with ethanol, and dry the crystals to obtain N-cyano-N'-(2-chloro-5-thiazole Base) acetamidine 96.6g, content 89%, yield 80.3%.

[0041] Add the N-cyano-N'-(2-chloro-5-thiazylmethyl)acetamidine (0.401mol) obtained above to the reaction flask, and add 200ml of chloroform, Bu 4 NB r (PTC) 0.03g, stir and cool to 10-15°C, add dropwise 55.5g (0.44mol) of dimethyl sulfate and 50% sodium hydroxide so...

Embodiment 2

[0043] Add 150ml of dried N,N-dimethylformamide into a dry glass reaction bottle, then add 84g (0.5mol) of pure 2-chloro-5-chloromethylthiazole, stir, and then carefully Add 12g (0.5mol) of pure NaH into a reaction flask at 10°C, stir for 15 minutes, then add 48.5g (0.5mol) of pure N-cyano-N'-methylacetamidine, raise the temperature to about 50°C, and stir for 6 Hours, slowly cooled to about 10°C, crystallized, filtered, the filter cake was washed with water, and dried to obtain 173.1g of yellow JT-L00, with a content of 80.2% and a yield of 51.16%.

Embodiment 3

[0045] In a 500ml ground glass reaction bottle, add 84g (0.5mol) of pure product 2-chloro-5-chloromethylthiazole, and dropwise add 59g (1.9mol) of pure product monomethylamine and 95% ethanol under stirring In 150ml pre-refrigerated mixed solution, keep at 0-5°C, stir evenly, raise the temperature to 40°C and react for 4 hours, evaporate ethanol and residual gas under negative pressure, adjust the pH to neutral, pour into a separatory funnel and let it stand for stratification After that, take the oil layer and use anhydrous Na 2 SO 4 After drying, 76.9 g of N-methyl-2-chloro-5-thiazole methylamine was obtained, with a content of 94.1% and a yield of 88.5%.

[0046] Add the mixed solution of 52g (0.46mol) of pure N-cyanoacetate and 100ml of absolute ethanol dropwise into the above reaction flask under stirring, keep the dropping temperature at 40°C, within 2.5h Drop the reaction, then heat up to reflux, react for 3h, cool and crystallize, filter, wash the filter cake with ab...

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Abstract

The invention discloses a new chemical synthesizing method of second-generation nicotinic insecticide JT-L001, whose chemical formula is N'-(2-chlorine-1, 3-thiazole-5-methyl)-N-cyano-N'-methyl acetamidine. The compound possesses high-activity and low-toxicity, which is compatible with environment.

Description

technical field [0001] The present invention relates to an organic compound, in particular to a compound N'-(2-chloro-1,3-thiazol-5-ylmethyl)-N-cyano-N'-methanol which can be used as an insecticide Acetamidine and its chemical synthesis method. Background technique [0002] Neonicotinoids are a new class of attractive chemical insecticides with excellent biological activity. Since Bayer developed imidacloprid in 1991, Nitenpyram was developed by Takeda in 1995, acetamiprid was developed by Soda Corporation in Japan in 1996, and Novartis (now the first) in 1998. Thiamethoxam developed by Zhengda, thiacloprid developed by Bayer in 2000, clothianidin developed by Takeda / Bayer in 2002, and dinotefuran developed by Mitsui Chemicals . At present, these varieties have been commercialized and listed in many countries in the world. Among them, only imidacloprid and acetamiprid have been put into industrial production in my country, and have become the first choice for the control ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/30A01N47/40A01P7/04
Inventor 许网保魏明阳缪留福刘文新吴仲芳虞国新
Owner JIANGSU TIANRONG GROUP
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