Preparation method of Metconazole

A technology of metconazole and chlorobenzylidene is applied in the field of preparation of metconazole, can solve problems such as long preparation route steps, unfavorable industrialization, etc., and achieves the effects of cheap raw materials, controllable safe operation, and improved conversion rate

Inactive Publication Date: 2019-09-06
九江德思光电材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the preparation route steps of 1-(4-chlorobenzyl)-2-hydroxyl-2-hydroxymethyl-3,3-dimethylcyclopentane as the key intermediate are generally longer, which is unfavorable for industrialization

Method used

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  • Preparation method of Metconazole
  • Preparation method of Metconazole
  • Preparation method of Metconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of methyl 1-methyl-2-oxocyclopentanecarboxylate

[0054] Add 2-methoxycarbonylcyclopentanone (200 g, 1.5 mol) and tetrahydrofuran (2 L) into a 5 L reaction flask, and lower the temperature to 0° C. under mechanical stirring. Potassium hydroxide (28 g, 0.5 mol) was added in batches, and after stirring for 30 min, a tetrahydrofuran solution of methyl bromide (110 mL, 2.0 mol) was added dropwise to the system, and the dropping temperature was controlled below 0°C. After the dropwise addition was complete, it was stirred for 12 hours. The reaction solution was poured into water, extracted three times by adding dichloromethane, the organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, concentrate in vacuo to remove the solvent, and distill under reduced pressure to obtain 204 g of methyl 1-methyl-2-oxocyclopentanecarboxylate with a yield of 93%.

Embodiment 2

[0056] Preparation of 2-methylcyclopentanone

[0057] Add methyl 1-methyl-2-oxocyclopentanecarboxylate (200g, 1.3mol), water (1.5L), concentrated sulfuric acid (7.5mL, 0.13mol) to the 5L reaction flask, and heat up to 100 °C for 10 hours. The system was cooled down to room temperature, extracted three times with ethyl acetate, the organic phases were combined, washed with 5% sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, evaporated to remove the solvent and then distilled under reduced pressure to obtain 120 g of 2-methylcyclopentanone. The rate is 95%.

Embodiment 3

[0059] Preparation of 2-(4-chlorobenzylidene)-5-methylcyclopentanone

[0060] Add p-chlorobenzaldehyde (155g, 1.1mol) and ethanol (1L) to a 2L reaction flask, control the temperature at about 0°C under mechanical stirring, and slowly add potassium tert-butoxide (122g, 1.1mol). After stirring for 30 minutes, a solution of 2-methylcyclopentanone (98 g, 1.0 mol) in ethanol was added. After stirring at room temperature for 3 hours, the reaction system was slowly poured into ice water, solids were precipitated, and stirring was continued for 2 hours. After suction filtration, beating and drying, 205 g of product 2-(4-chlorobenzylidene)-5-methylcyclopentanone was obtained, with a yield of 93%, and a content of 97.9%. 1 H-NMR (400MHz, CDCl 3 )δ7.48-7.43(m,2H),7.40-7.35(m,2H),7.34(t,J=2.8Hz,1H),2.96(m,1H),2.78(m,1H),2.44-2.28 (m,2H),1.59-1.46(m,1H),1.20(d,J=6.5Hz,3H). 13 C-NMR (100MHz, CDCl 3 )δ209.3, 136.5, 135.1, 134.1, 131.6, 131.0, 128.9, 43.3, 29.2, 27.5, 14.6. HRMS (EI): ca...

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Abstract

The invention discloses a preparation method of Metconazole, and the method comprises the following steps: carrying out water decarboxylation on a methylated product obtained by methylation of 2-methoxy acyl cyclopentanone to obtain 2-methyl cyclopentanone; reacting 2-methyl cyclopentanone with p-chlorobenzaldehyde to obtain 2-(4-chlorobenzylidene)-5-methyl cyclopentanone; carrying out methylationto obtain 5-(4-chlorobenzylidene)-2,2-dimethyl cyclopentanone; 5-(4-Chlorobenzylidene)-2,2-dimethylcyclopentanone undergoes Corey-Chaykovsky reaction to obtain an epoxide; reacts the epoxide with triazole to obtain a ring-opening product; and carrying out catalytic hydrogenation on the ring-opening product to obtain the Metconazole. The raw materials adopted by the preparation method are low in cost and easy to obtain in the market. The reactions in each step are conventional, the reaction steps are simple and easy to implement, and the method is simple process, mild in reaction conditions and easy in operation. The method has the advantages of high conversion rate, short reaction time and easy control, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a method for preparing metconazole. Background technique [0002] Metconazole, the common name in English is Metconazole, and the trade name is Caramba. It is a triazole fungicide. Like other triazole fungicides, it has the characteristics of broad antibacterial spectrum and strong systemic absorption. The mechanism of action of these fungicides is to play a bactericidal effect by inhibiting the C-14 demethylase cytochrome in sterol biosynthesis. Meconazole is mainly used for the prevention and treatment of dwarf rust, leaf rust, yellow rust, crown rust, powdery mildew, glume blight and diseases caused by Septoria spirochete and Fusarium paniculata in grass crops. It can also be used as a horticultural fungicide. agent. Since it was registered as a fungicide in France in 1994, the registration countries of this product have been increasing, and it has become a registered pes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D303/08C07D301/02
CPCC07D249/08C07D303/08C07D301/02
Inventor 杨红光罗佳范云龙孙亚军
Owner 九江德思光电材料有限公司
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