Preparation method of spiromesifen

A technology of spiromethin and trimethylphenylacetyl, which is applied in the field of preparation of spiromethin, can solve the problems of unfavorable industrial production, complex and time-consuming process, and low reaction yield, so as to achieve sufficient raw material sources and simple process Effective, high-yield effect

Inactive Publication Date: 2008-08-27
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

It has the following disadvantages: firstly, the product obtained in each step of the reaction needs to be separated and purified by silica gel column, the process is complicated and time-consuming; secondly, the reaction yield is relatively low, which does not meet the requirements of current green chemistry; finally, the cyclization reaction requires reduced pressure conditions , the process is complicated, which is not conducive to industrial production
[0004] Wherein the synthetic method of 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4.4]-non-3-ene 4-ol has not been reported yet

Method used

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  • Preparation method of spiromesifen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the preparation of compound II, i.e. 1-[2-(2,4,6-trimethylphenyl)-acetoxy]-cyclopentylcarboxylic acid:

[0035] Add 8.0g (61.5mmol) 1-carboxycyclopentanol, 13.5g (171mmol) pyridine, 60mL dichloromethane into the reaction flask, drop 15.6g (79.3mmol) 2,4 , The dosing of 6-trimethylphenylacetyl chloride and 40mL of dichloromethane. After the dropwise addition was completed within 1 h, the stirring reaction was continued at room temperature for 12 h.

[0036] After the reaction was completed, it was concentrated, 100 mL of 3% HCl was added, extracted three times with ethyl acetate, and washed with water. Anhydrous Na 2 SO 4 Drying and concentration yielded 15.9 g of product as a brown solid, Y=89.2%.

Embodiment 2

[0037] Example 2, the preparation of compound III, namely 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4.4]-non-3-en 4-ol:

[0038] Add 10.6g (36.5mmol) 1-[2-(2,4,6-trimethylphenyl)-acetoxy]-cyclopentyl formic acid, 5.0g ( 44mmol) magnesium ethylate and 120mL of ethanol, heated to reflux for 12h.

[0039] After the reaction was over, after most of the solvent was evaporated under reduced pressure, 50 mL of 3% hydrochloric acid was added, extracted three times with ethyl acetate, and then washed with water, anhydrous Na 2 SO 4 Drying and concentration yielded 7.2 g of solid product, Y=72.5%.

Embodiment 3

[0040] Example 3, Spiromethazol, namely 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4.4]-non-3-en 4-yl-3 , the preparation of 3-dimethylbutyl ester:

[0041] Add 2.0 g (7.4 mmol) of 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4.4]-nonan-3 obtained in Example 2 above to the reaction flask -en 4-alcohol and 3.0g (30.0mmol) triethylamine and 50mL dichloromethane, then add dropwise 1.3g (9.7mmol) 3,3-dimethylbutyryl chloride, and stir the reaction at room temperature (ie 0~30°C) 2h.

[0042] After the reaction, the resulting reaction solution was washed three times with 1% hydrochloric acid, and then washed with saturated NaHCO 3 The solution was washed twice, and finally washed twice with water, anhydrous Na 2 SO 4 Drying and concentration afforded 2.9 g of solid product. After recrystallization from 95% ethanol, 2.5 g of product was obtained, Y=93.1%, content 90%-95%. Finally, the product with a content of more than 99% was obtained through silica gel column purification.

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Abstract

The invention discloses a preparation method of spiromesifen, which uses 1-carboxyl cyclopentanol, 2, 4, 6-trimethylbenzene dichloroacetyl chloride and 3, 3-dimethyl butyryl chloride as main materials. The preparation method comprises (1), generating compound II: reacting 1-carboxyl cyclopentanol and 2, 4, 6-trimethylbenzene dichloroacetyl chloride in the presence of catalyst and in organic solvent, (2), generating compound III by heating the compound II and strong alkali in alcohol solution or in aprotic strong polar solvent to process reflux reaction, (3), generating spiromesifen by reacting the compound III and 3, 3-dimethyl butyryl chloride in the presence of catalyst and in organic solvent, wherein the prepared spiromesifen is represented as above. The preparation method of spiromesifen is suitable for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of spiromethimen, namely a kind of 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4.4]-nonan- Process for the preparation of 3-en-4-yl-3,3-dimethylbutyl ester. Background technique [0002] Spiromethin is a second-generation spirotetronic acid insecticide and acaricide developed by Bayer. It is mainly used for the control of whitefly and spider mites in cotton, vegetables and ornamental plants. The mechanism of action of spiromethin is to affect the development of whiteflies and mites, interfere with the biosynthesis of their liposomes, especially have good activity on the larval stage, and at the same time, it can also produce ovariectal closure, reducing the incidence of mites and whitefly adults. reproductive capacity, greatly reducing the number of eggs laid. Spiromethin can effectively control whiteflies that are resistant to pyriproxyfen, and it can effectively control resistant whiteflies when ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/94A01N43/12A01P7/00
Inventor 赵金浩徐旭辉周勇程敬丽朱国念
Owner ZHEJIANG UNIV
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