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High purity metconazole and preparation method thereof

A metconazole and high-purity technology, which is applied in the field of high-purity metconazole and its preparation, can solve the problems of unobtainable raw materials, poor economy, long route and the like, and achieves short route, high yield and good atom economy. Effect

Active Publication Date: 2015-06-17
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0033] The purpose of the present invention is to provide a high-purity metconazole and its its preparation method

Method used

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  • High purity metconazole and preparation method thereof
  • High purity metconazole and preparation method thereof
  • High purity metconazole and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0061] The synthesis of embodiment 1,2-(4-chlorobenzylidene) cyclopentanone (II)

[0062] In a dry 150mL single-necked bottle, add pyrrolidine (1mL, 0.0078mol, 0.1eq), add tetrahydrofuran (70mL), cyclopentanone (6.9mL, 0.078mol, 1.0eq), p-chlorobenzaldehyde (11.0g, 0.078mol , 1.0eq), stirred at 25°C for 6 hours. Ethyl acetate was added for extraction and liquid separation. After spin-drying, the target product was obtained with a yield of 68%.

[0063] 1 H NMR (400MHz, CDCl 3 ): δ7.45-7.47(d, 2H), 7.37-7.39(d, 2H), 7.32-7.33(t, 1H), 2.93-2.97(td, 2H), 2.39-2.43(t, 2H), 2.01 -2.08(p, 2H).

Embodiment 2

[0064] The synthesis of embodiment 2,2-(4-chlorobenzylidene) cyclopentanone (II)

[0065] In a dry 250mL single-necked bottle, add KOH (2.2g, 0.039mol, 0.5eq), add water (95mL), stir to dissolve, add dichloromethane (70mL), cyclopentanone (6.9mL, 0.078mol, 1.0eq) . p-Chlorobenzaldehyde (13.2g, 0.094mol, 1.2eq), stirred at 25°C for 12 hours. Ethyl acetate was added for extraction and liquid separation. After spin-drying, the target product was obtained with a yield of 85%.

Embodiment 3

[0066] The synthesis of embodiment 3,2-(4-chlorobenzylidene) cyclopentanone (II)

[0067] In a dry 150ml single-necked bottle, add methanesulfonic acid (50μL, 0.00078mol, 0.01eq), add dimethyl sulfoxide (70mL), cyclopentanone (6.9mL, 0.078mol, 1.0eq), p-chlorobenzaldehyde (8.8 g, 0.062mol, 0.8eq), reflux (189°C) and stir for 1 hour. Ethyl acetate was added for extraction and liquid separation. After spin-drying, the target product was obtained with a yield of 83%.

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Abstract

The invention discloses high purity metconazole and a preparation method thereof; the preparation is as follows: exocyclic double bond alpha, beta-unsaturated ketone (II) can be obtained by condensation reaction of cyclopentanone and p-chlorobenzaldehyde; then the exocyclic double bond alpha, beta-unsaturated ketone (II) is reacted with a methylation reagent to obtain alpha', alpha'-dimethyl substituted exocyclic double bond alpha, beta unsaturated ketone (III); then in the presence of a catalyst, the alpha', alpha'-dimethyl substituted exocyclic double bond alpha, beta unsaturated ketone (III) is reacted with hydrogen to obtain 2, 2-dimethyl-5-(4-chloro-benzyl) cyclopentanone (IV) with the double bond being reduced; an epoxypropane compound (V) is obtained by Johnson-Corey-Chaykovsky of the reduced product (IV); finally the epoxypropane compound (V) is reacted with 1, 2, 4 - triazole, and then the high purity metconazole (I) can be obtained by recrystallization. The preparing method has the advantages of chip and easy available raw materials, short route, good selectivity, high overall yield and good atom economy, and is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the fields of pesticides and chemicals, and in particular relates to a high-purity metconazole and a preparation method thereof. Background technique [0002] Metconazole (common name Metconazole), a triazole fungicide that was developed by Japan Kureha Chemical Industry Company in 1986 and launched in 1994 after being jointly developed with American Cyanoamide Company (now BASF). Its pure product is a mixture of cis and trans forms, white, crystalline solid, good thermal and hydrolytic stability, and high cis activity. [0003] Meconazole acts by inhibiting the C-14 demethylase (cytochrome P45014DM) biochemically synthesized by the biofilm component of plant pathogenic bacteria, ergosterol. Compared with other triazole fungicides, the activity spectrum is quite different. Both isomers have bactericidal activity, but the cis form is higher than the trans form. It is mainly used for the prevention and treatment of dwarf rust, ...

Claims

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Application Information

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IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 张万斌张振锋陈树生施冠成
Owner SHANGHAI JIAO TONG UNIV
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