Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron

A technology of difluorobenzamide and difluorobenzoyl isocyanate is applied in the field of synthesis of insecticide fuzuron and its intermediate 2,6-difluorobenzamide, which can solve the pressure of environmental protection and the process route It can improve the yield and quality, shorten the reaction route and reduce the pressure of environmental protection.

Active Publication Date: 2020-11-27
SHANGYU JINTENG MEDICAL CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. The process route is long, the yield is low, and the total yield is about 55.4%, resulting in relatively high cost;
[0008] 2. The amount of waste water is very large, mainly because a large amount of waste water is produced during the synthesis process of compound 2→5, which has caused great environmental protection pressure;
[0009] 3. In the first step of chlorination reaction, the chlorination conditions are not easy to control, and there are many isomers and impurities. At present, the general yield of chlorination reaction is 94.5%, and the content is 97%;
[0010] 4. Fluorination reaction, the amount of tar in the synthesis process of compound 6 is relatively lar

Method used

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  • Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron
  • Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron
  • Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: The synthesis of compound 2→5 was completed by "one-pot method".

[0057] Set the reaction temperature to 150°C in the CORNING G1-10FM SiC high-flux microchannel reactor, pump the suspension prepared by stirring 1610g2,6 dichlorotoluene and 15g phosphorus pentachloride at a flow rate of 20mL / min, 40g / Chlorine gas is introduced at a flow rate of min, the material is introduced into the gas-liquid separator filled with water, and the tail gas is passed into the tail gas absorption device. Open the gas-liquid separator bottom valve, separate layers, the water layer is reclaimed hydrochloric acid, as a by-product, and the organic layer is crude product. The main fraction was collected by rectification of the crude product to obtain 222 g of 2,6-dichlorobenzylidene dichloride, with a content of 99% and a yield of 97.0%;

[0058] 57.5 g of 2,6-dichlorobenzylidene dichloride, 300 g of 85% acetic acid, 0.5 g of zinc chloride, 21 g of hydroxylamine hydrochloride and...

Embodiment 4

[0081]

[0082] Table (one): content and yield result table of embodiment one compound 2, 5, 6, 7, 8 and 9

[0083]

[0084] Table (two): content and yield result table of embodiment two compounds 2, 5, 6, 7, 8 and 9

[0085]

[0086] Table (three): content and yield result table of embodiment three compounds 2, 5, 6, 7, 8 and 9

[0087] By comparing and analyzing the above three tables, we found the following results:

[0088] 1. The total yield of Example 1 is about 67.7%, and the total yield of Example 2 is about 70.4%, which is greatly improved compared with the existing 55.4%. Compound 2→5 adopts "one pot method" After completion, the yield of Compound 5 in Example 1 was 94%, with a content of 99.7%, and the yield of Compound 5 in Example 2 was 93.6%, with a content of 99.5%. The yields were all above 93%, and the content was higher than 99.5%.

[0089]2, embodiment one, embodiment two and embodiment three all adopt microchannel chlorination reaction to synthes...

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Abstract

The invention discloses a synthesis method of an insecticide teflubenzuron and an intermediate 2,6-difluorobenzamide of the insecticide teflubenzuron, belonging to the field of pesticides. The synthesis method comprises the following steps: step 1, preparation of 2,6-dichlorobenzylidene chloride: preparing turbid liquid of dichlorotoluene and phosphorus pentachloride, introducing chlorine gas, layering materials by utilizing a gas-liquid separator, collecting a crude product, and rectifying the crude product to obtain the 2,6-dichlorobenzylidene chloride; and 2, preparation of 2,6-dichlorobenzonitrile: mixing 2,6-dichlorobenzylidene chloride, acetic acid, zinc chloride, hydroxylamine hydrochloride and sodium acetate, carrying out heating for a reflux reaction, conducting cooling, stirring,filtering and drying successively after the reaction is completed so as to obtain 2, 6-dichlorobenzonitrile. By adopting a one-pot method, a reaction route is shortened, total yield is increased to 67.3% from conventional 55.4%, and cost is greatly reduced.

Description

technical field [0001] The invention relates to the field of insecticides, and more specifically relates to a synthesis method of the insecticide furbenuron and its intermediate 2,6-difluorobenzamide. Background technique [0002] Teflubenzuron is a benzoylurea insecticide developed by Celamerck GmbH & Co. in 1984 and launched in 1986. After several acquisitions, it is now owned by BASF. The chemical name of pyriobron is 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea, and the English name is 1-(3,5 -dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzyl)urea, CAS number: 83121-18-0, molecular formula: C14H6Cl2F4N2O2, molecular weight: 381.11, chemical structural formula: [0003] [0004] At present, the method of synthesizing pyroxanuron is mainly based on 2,6-dichlorotoluene as the starting material, and the intermediate 2,6-difluorobenzamide is obtained through 6 steps of reaction, and then 2 steps are used to obtain pyroxanuron, as shown in the figure be...

Claims

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Application Information

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IPC IPC(8): C07C231/06C07C233/66C07C273/18C07C275/54C07C17/14C07C25/02C07C263/10C07C265/16C07C253/30C07C255/50
CPCC07C231/06C07C273/1827C07C263/10C07C253/30C07C253/00C07C17/14C07C275/54C07C265/16C07C233/66C07C255/50C07C25/02
Inventor 易苗尹凯杨江宇吴浩吴文良于江顾旻旻柴华强
Owner SHANGYU JINTENG MEDICAL CHEM IND
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