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Process for the preparation of fungicidally active strobilurin compounds and intermediates thereof

A compound and halogen technology, applied in the field of preparation of intermediates that can be used to prepare the strobilurin compound, can solve problems such as complex separation procedures

Pending Publication Date: 2021-12-21
UNITED PHOSPHORUS LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Impurities formed during the initial synthesis stage can lead to a series of side reactions
In addition, the final product will require a complex separation process

Method used

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  • Process for the preparation of fungicidally active strobilurin compounds and intermediates thereof
  • Process for the preparation of fungicidally active strobilurin compounds and intermediates thereof
  • Process for the preparation of fungicidally active strobilurin compounds and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0442] (E) Preparation of methyl 2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (IIa):

[0443] At 10 °C, 4,6-dichloropyrimidine (98%, 92 g, 0.605 mol) was added to 3-(methoxymethylene)-2(3H)-benzofuranone (97%, 91 g, 0.5 mol) in a stirred mixture in methyl formate (275 g). At 10 °C to 15 °C, 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (0.035 g, 0.25 mmol, 0.05 mol%) was added to the reaction mixture followed by dropwise addition of methanol Sodium (30% in methanol, 110 g, 0.61 mol). After the addition, the reaction mass was stirred at 10°C to 15°C for 1 hour. The methyl formate was then distilled off while keeping the temperature below 55°C. Toluene (300ml) and water (200ml) were added to the residue, and the mixture was stirred at 60°C to 65°C. The mixture was cooled to room temperature, and the organic layer was separated. The solvent was distilled off from the reaction mixture under reduced pressure, and the oily residue was heated to 130°C to 135°C. Potassium bis...

Embodiment 2

[0444] Embodiment 2 (comparative example)

[0445] Preparation of (E)-methyl 2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (IIa) in the absence of catalyst:

[0446] To a stirred mixture of 3-(methoxymethylene)-2(3H)-benzofuranone (97%, 91 g, 0.5 mol) in methyl formate (275 g) was added 4, 6-Dichloropyrimidine (98%, 92 g, 0.605 mol). Sodium methoxide (30% in methanol, 110 g, 0.61 mol) was added dropwise to the reaction mixture at 10°C to 15°C. After the addition, the reaction mass was maintained at 10°C to 15°C for 1 hour. The methyl formate was distilled at atmospheric pressure while maintaining the temperature below 55 °C. To the residue were added toluene (300 mL) and water (200 mL), and the mixture was heated at 60°C to 65°C. The mixture was cooled to room temperature, and the organic layer was separated. Toluene was distilled off under reduced pressure, and the oily residue was heated at 130°C to 135°C to remove the solvent. Potassium bisulfate (1.36 g, ...

Embodiment 3

[0448] Preparation of azoxystrobin (Ia)

[0449] At room temperature, methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (83.5g, 0.25mol), potassium carbonate (52.8 1,5,7-triazabicyclo[4.4.0]dec-5-ene ( 0.695 g, 0.005 mol, 2.0 mol%) in DMF (10 mL). The mixture was heated to 90°C and stirred at the same temperature for 7 to 8 hours. The reaction mixture was cooled to 50°C to 55°C and filtered to remove salts. DMF was distilled at 70°C to 80°C under vacuum. The residual material was crystallized from a mixture of methanol (90 mL) and water (10 mL) to give the product (98% purity, 0.78% dimer content).

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Abstract

The present invention relates to a process for the preparation of strobilurin of compounds of Formula (I) of and its intermediates using 1,5,7-triazabicyclo[4.4.0]dec-5-ene or salts thereof, or derivatives thereof as a catalyst. The present invention provides the compounds of formula (I) in high yield and high purity.

Description

technical field [0001] The present invention relates to a method for preparing a fungicidally active strobilurin compound represented by formula (I). The present invention also relates to a process for the preparation of intermediates useful for the preparation of said strobilurin compounds, [0002] Background technique [0003] Strubilurins are broad-spectrum fungicides and are widely used insecticides in foliar applications and seed treatments. Owing to their broad-spectrum activity profile, strobilurins are an important class of fungicides. Notable among this class of compounds are azoxystrobin, trifloxystrobin, fluoxastrobin and picoxystrobin. [0004] EP 382375 discloses various derivatives of acrylic acid, including azoxystrobin, useful as fungicides. The patent also discloses a method for preparing azoxystrobin and its intermediates. [0005] US6103717 discloses halopyrimidine compounds, their preparation and their use as insecticides. [0006] The convention...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52C07D413/12C07B41/04
CPCC07D413/12C07D239/52C07B41/04
Inventor 普拉尚·瓦桑特·基尼桑托什·甘帕特·谢尔克
Owner UNITED PHOSPHORUS LTD
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