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Preparation method of ammonia base formate kind agricultural pesticide hapten

A carbamate and nitrobenzene haloformate technology is applied in the field of new preparation of carbamate pesticide haptens, and can solve the problems of increasing the difficulty of operation, environmental pollution, increasing danger and the like

Inactive Publication Date: 2006-01-25
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This synthesis method uses a large amount of phosgene, and phosgene is a highly toxic gas, and must avoid leakage during operation, which increases the difficulty of operation and the danger in production, and Very easy to cause environmental pollution

Method used

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  • Preparation method of ammonia base formate kind agricultural pesticide hapten
  • Preparation method of ammonia base formate kind agricultural pesticide hapten
  • Preparation method of ammonia base formate kind agricultural pesticide hapten

Examples

Experimental program
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Effect test

Embodiment 1

[0016] After dissolving 0.8g of naphthol in 20ml of anhydrous dichloromethane, add 0.58ml of anhydrous pyridine to form a mixed solution, and add dropwise anhydrous dichloromethane solution dissolved with 1g of p-nitrobenzene chloroformate in this mixed solution 15ml, the whole system was kept at -4°C-6°C. The reaction was protected with nitrogen and kept anhydrous. The reaction was followed by thin-plate chromatography (TLC) to determine the reaction time. Recrystallize from dichloromethane and ether. Light yellow 1-naphthyl p-nitrophenyl carbonate crystals were obtained with a yield of 80%. Characterized by infrared spectroscopy, there are characteristic peaks of carbonyl and nitro (attached figure 1 ). The correctness of the structure of the obtained product was further proved by proton nuclear magnetic resonance spectrum. (attached figure 2 )

[0017] Dissolve 1.2 mmol of 1-naphthyl p-nitrophenyl carbonate obtained in the previous step in tetrahydrofuran, dissolve ...

Embodiment 2

[0019] After 0.6g of 3-methylphenol was dissolved in 15ml of anhydrous dichloromethane, 0.58ml of anhydrous pyridine was added to form a mixed solution, and 1g of p-nitrophenyl chloroformate was added dropwise to the anhydrous dichloroformate in this mixed solution. Chloromethane solution 15ml, the whole system was kept at -4°C-6°C. The reaction was protected with nitrogen and kept anhydrous. The reaction was followed by TLC to determine the reaction time. Recrystallize from dichloromethane and ether. Light yellow 3-methylphenyl-p-nitrobenzene carbonate crystals were obtained with a yield of 87%. Characterized by infrared spectroscopy, there are characteristic peaks of carbonyl and nitro groups, and the correctness of the structure of the obtained product is further proved by hydrogen nuclear magnetic resonance.

[0020] Dissolve 1.2 mmol of 3-methylphenyl-p-nitrobenzene carbonate obtained in the previous step in tetrahydrofuran, dissolve 0.16 g of 6-aminocaproic acid in so...

Embodiment 3

[0022] After 0.8g of 3,4-xylenol was dissolved in anhydrous 15ml of methylene chloride, 0.58ml of anhydrous pyridine was added to form a mixed solution, and 1g of p-nitrophenyl chloroformate was added dropwise to the mixed solution. 15ml of anhydrous dichloromethane solution, and the whole system was kept at -4°C-6°C. The reaction was protected with nitrogen and kept anhydrous. The reaction was followed by TLC to determine the reaction time. Recrystallize from dichloromethane and ether. Light yellow 3,4-dimethylphenyl-p-nitrobenzene carbonate crystals were obtained with a yield of 85%. Characterized by infrared spectroscopy, there are characteristic peaks of carbonyl and nitro groups, and the correctness of the structure of the obtained product is further proved by hydrogen nuclear magnetic resonance.

[0023] Dissolve 1.2 mmol of 3,4-dimethylphenyl-p-nitrobenzene carbonate obtained in the previous step in tetrahydrofuran, dissolve 0.16 g of 6-aminocaproic acid in sodium bi...

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Abstract

The invention provides a new method for synthesizing half-antigen of carbamate pesticide, including the steps: (1) using para-nitrobenzene halogenated formate to activate hydroxyl functional group-containing compound so as to obtain para-nitrobenzene carbonate compound; (2) using the para-nitrobenzene carbonate compound as raw material to synthesize the half-antigen of carbamate pesticide. Compared with the traditional methods, the invention avoids using toxic gas-phosgene, strengthening production safety and reducing pollution to the environment and raising the yield of reaction.

Description

technical field [0001] The invention belongs to the field of pesticide residue detection and relates to a new preparation method of carbamate pesticide hapten. Background technique [0002] The environmental toxicity problem caused by the extensive use of pesticides has aroused people's great attention. Carbamate insecticides are an important branch in the field of pesticide chemistry. Together with organophosphates and pyrethroids, they have become the main body of insecticides. There are more than 40 commercial varieties, among which there are more than 10 varieties with large tonnage. In the world insecticide market in 1989, the sales of carbamate insecticides accounted for 21% of the total sales of insecticides, ranking second only to organophosphorus. In recent years, due to the prohibition of organochlorine pesticides and the increase of insect species resistant to organophosphorus insecticides, the amount of carbamates has increased yea...

Claims

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Application Information

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IPC IPC(8): G01N33/532
Inventor 马光辉苏志国杨耀军孟凡涛
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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