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Preparation method of iprodione

A technology of isofluranil and catalyst, applied in the field of preparation of isoflubenzuron, can solve the problems of uneconomical, low utilization rate, large amount of three wastes, etc., and achieve the advantages of improving the utilization rate of production equipment, shortening production steps, and reducing preparation cost. Effect

Active Publication Date: 2017-10-13
XINYI AGRI CHEM PLANT JIANGSU PROV
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  • Abstract
  • Description
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Problems solved by technology

This kind of process equipment requires a lot of investment, the utilization rate is not high, and the amount of three wastes produced is large, which is uneconomical and not environmentally friendly.
Moreover, in the prior art, it is necessary to separate 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione, resulting in a large amount of waste water, difficult centrifugation and other disadvantages

Method used

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  • Preparation method of iprodione
  • Preparation method of iprodione
  • Preparation method of iprodione

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preparation example Construction

[0021] The present invention provides a kind of preparation method of iprodione, comprising:

[0022] Mix N-[[(3,5-dichlorophenyl)amino]carbonyl]aminoacetic acid with an organic solvent, and react under the action of catalyst A to generate 3-(3,5-dichlorophenyl)-2,4- Imidazolidinedione, wherein, catalyst A is the mixture of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid;

[0023] React 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione with isopropyl isocyanate under the action of catalyst B and catalyst C to generate iprodione, wherein catalyst B is carbonic acid A mixture of ammonium, sodium bicarbonate, sodium carbonate and liquid ammonia, catalyst C is a mixture of pyridine and triethylamine.

[0024] In the present invention, N-[[(3,5 dichlorophenyl)amino]carbonyl]aminoacetic acid (commonly known as "uric acid" in the industry) is:

[0025]

[0026] 3-(3,5-dichlorophenyl)-2,4C-l imidazolidinedione O is:

[0027]

[0028] The specific chemi...

Embodiment 1

[0040] Add 92g of N-[[(3,5 dichlorophenyl)amino]carbonyl]aminoacetic acid (Mr=263, 0.34mol , 98% industrial product), 400ml organic solvent and 12g catalyst A (0.13 times the mass of uric acid), start stirring, heat the mixture to 90°C, and reflux with water for 4-6h. Add 40g (Mr=85, 0.47mol, 99%, industrial product) of isopropyl isocyanate, 16g of catalyst B (0.17 times the mass of uric acid), and 14g of catalyst C (0.15 times the mass of uric acid) into the reaction flask, and dropwise , heat preservation reaction for 8-10h, after the heat preservation is completed, wash with water, precipitate from the solvent, filter, and dry to obtain 103g of iprodione, with a content of 96.8% and a yield of 88.2%.

[0041] In catalyst A, the mass ratio of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid is 1:1:1. In catalyst B, the mass ratio of ammonium carbonate, sodium bicarbonate and sodium carbonate is 1:1:3; in catalyst C, the mass ratio of pyridine and ...

Embodiment 2

[0043]Add 92g of N-[[(3,5 dichlorophenyl)amino]carbonyl]aminoacetic acid (Mr=263, 0.34mol , 98% industrial product), 400ml organic solvent and 12g catalyst A (0.13 times the mass of uric acid), start stirring, heat the mixture to 120°C, and reflux with water for 4-6h. Add 40g (Mr=85, 0.47mol, 99%, industrial product) of isopropyl isocyanate, 16g of catalyst B (0.17 times the mass of uric acid), and 14g (0.15 times the mass of uric acid) of catalyst C into the reaction flask, and dropwise , heat preservation reaction for 8-10 hours, after the heat preservation is completed, wash with water, precipitate from the solvent, filter, and dry to obtain 105 g of iprodione, with a content of 97.5% and a yield of 90.6%.

[0044] In catalyst A, the mass ratio of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid is 1:1:1. In catalyst B, the mass ratio of ammonium carbonate, sodium bicarbonate and sodium carbonate is 1:1:3; in catalyst C, the mass ratio of pyridin...

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Abstract

The invention discloses a preparation method of iprodione, which comprises of mixing N-[[(3,5 dichlorophenyl) amino] carbonyl] glycine with an organic solvent to react by the action of a catalyst A to generate 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione, and allowing 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione to react with isopropyl isocyanate by the action of a catalyst B and a catalyst C to generate iprodione, wherein the catalyst A is a mixture of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid; the catalyst B is a mixture of ammonium carbonate, sodium bicarbonate and sodium carbonate; and the catalyst C is a mixture of pyridine and triethylamine. A content of the finished product, namely iprodione prepared by the method reaches above 97%, and the preparation cost of iprodione is greatly lowered.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, in particular to a preparation method of iprodione. Background technique [0002] Iprodione (English common name is Iprodione, alias: prodione), 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, insoluble in water, easily soluble In organic solvents such as acetone and dimethylformamide, it will decompose in case of alkali, non-hygroscopic and non-corrosive. Iprodione is a dicarboximide high-efficiency broad-spectrum, contact fungicide. It is suitable for the prevention and control of early leaf defoliation, gray mold, early blight and other diseases of various fruit trees, vegetables, melons and other crops. [0003] All the synthesis methods of this product currently on the market are to use 3.5-dichloroaniline, isopropylamine and glycine as starting raw materials, organic solvents such as xylene as solvents, utilize phosgene to synthesize corresponding isocyanates, and then synthesize ...

Claims

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Application Information

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IPC IPC(8): C07D233/80
CPCC07D233/80
Inventor 纪传武张贤振蒋磊周全义孙新
Owner XINYI AGRI CHEM PLANT JIANGSU PROV
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