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Method for synthesizing spirodiclofen

A synthesis method and a technology for spirodiclofen, applied in the field of spirodiclofen, can solve problems such as being unsuitable for industrialized production, and achieve the effects of increasing the reaction yield and simplifying the process

Inactive Publication Date: 2008-08-06
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It can be seen that the product needs to be purified through a silica gel column, which is not suitable for industrial production

Method used

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  • Method for synthesizing spirodiclofen
  • Method for synthesizing spirodiclofen
  • Method for synthesizing spirodiclofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、2

[0043] Embodiment 1,2, the preparation of 4-dichlorophenylacetic acid-1-cyanocyclohexyl ester (compound II):

[0044] Add 7.9g (63.4mmol) of the above-mentioned 1-cyanocyclohexanol, 13.9g (175mmol) of pyridine, and 60mL of dichloromethane into the reaction flask, and add 20.0 The dosing of g (89.6mmol) 2,4-dichlorophenylacetyl chloride and 40mL dichloromethane. After the dropwise addition was completed for about 1h, the stirring reaction was continued for 12h.

[0045] After the reaction was finished, concentrate, add 100mL 3% (V / V) HCI, extract three times with ethyl acetate, the ethyl acetate layer was washed with 5% (W / W) Na 2 CO 3 The solution was washed twice and finally with water. Anhydrous Na 2 SO 4 Drying and concentration gave 28.9 g of a brown paste, which was washed with tert-butanol to give 13.4 g of the product, yield Y=77.2%.

Embodiment 2、1

[0046] Example 2, the preparation of 1-[2-(2,4-dichloro-phenyl)-acetoxy]-cyclohexanemethylcarboxylate (compound III):

[0047] Add 10.0g (32.2mmol) 2,4-dichlorophenylacetic acid-1-cyanocyclohexyl and 80ml concentrated sulfuric acid methanol solution after washing with tert-butanol obtained in the above-mentioned embodiment 1 and heat and stir to reflux Reaction 20h. This 80ml concentrated sulfuric acid methanol solution is made by distilling 8mL of concentrated sulfuric acid with methanol.

[0048] After the reaction was completed, most of the methanol was evaporated, and 50 mL of water was added after cooling, and the product was extracted 3 times with ethyl acetate, and the combined ethyl acetate layers were washed with 5% (W / W) NaHCO 3 solution was washed 3 times, and then washed with water, anhydrous Na 2 SO 4 Drying and concentration gave 8.6 g of product, Y=77.8%.

Embodiment 3

[0049]Example 3, Preparation of 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]-dec-3-ene 4-ol (compound IV):

[0050] Add 8.0g (23.1mmol) 1-[2-(2,4-dichloro-phenyl)-acetoxyl group]-cyclohexanemethyl carboxylate, 1.8g ( 16mmol) magnesium ethylate and 200mL of ethanol, heated to reflux for 12h.

[0051] After the reaction, evaporate most of the solvent; then add 5% hydrochloric acid to adjust the pH to acid; then extract with ethyl acetate, then wash with water, anhydrous Na 2 SO 4 Drying and concentration yielded 5.6 g of solid product, Y=77.3%.

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Abstract

The invention discloses a synthesis method of spirodiclofen which uses 1-cyano cyclohexanol, 2, 4-dichlorobenzene acetyl chloride and 2, 2-dimethyl butyryl chloride as main materials. The synthesis method comprises (1) generating compound II as 2, 4-dichlorobenzene acetic acid-1-cyano cyclohexyl, (2) generating compound III as 1-[2-(2, 4-dichloro-phenyl)-acetoxy]-cyclohexane methyl formate, (3) generating compound IV as 3-(2, 4-dichlorophenyl)-2-oxo-1-oxaspiro [4. 5]-sebacic-3-ene 4-alcohol, (4), generating compound I as 3-(2, 4-dichlorophenyl)-2-oxo-1-oxaspiro [4. 5]-sebacic-3-ene 4-radical-2, 2-dimethyl butyl. The spirodiclofen synthesis method has high yield and support for industrial production.

Description

technical field [0001] The present invention relates to a spirodiclofen, namely 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]-dec-3-en 4-yl-2,2- Synthetic method of dimethyl butyl ester. Background technique [0002] Spirodifen, also known as quaternary ketodiclofen, is the first keto-enol type insecticide / miticide developed by Bayer, and is an active ingredient of the pesticide product "mite danger". Mite Danger is a brand-new, high-efficiency non-systemic foliar treatment acaricide, which has good control effect and excellent long-lasting effect on different types of acarids in various crops, killing both eggs and young (if) mites, especially for the control of harmful mites resistant to existing acaricides. The mechanism of action of spirodiclofen is to inhibit fat synthesis in harmful mites. It has no cross-resistance with existing acaricides and is suitable for controlling harmful mites that are resistant to existing acaricides. Acarid has good contact killing activi...

Claims

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Application Information

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IPC IPC(8): C07D307/94A01P7/02A01P7/00
Inventor 赵金浩程敬丽徐旭辉周勇朱国念
Owner ZHEJIANG UNIV
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