Method for preparing trifloxystrobin

A technology of trifloxystrobin and methyl ketoxime, which is applied in the field of trifloxystrobin preparation and can solve the problems of complex process and high cost

Inactive Publication Date: 2011-01-12
YUEYANG DIPU CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to overcome the disadvantages of complicated process and high cost in the pri

Method used

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  • Method for preparing trifloxystrobin
  • Method for preparing trifloxystrobin
  • Method for preparing trifloxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Synthesis of 2-(2'-methylphenyl)-2-oxomethyl acetate

[0051] Dissolve 9.2g (0.1mol, percent) of toluene and 20.0g (0.15mol, percent) of anhydrous aluminum trichloride in 46g of dichloroethane, cool to 5°C with an ice bath, and slowly add oxalyl chloride mono Methyl ester 14.7g (0.12mol, percent), react at room temperature after completion of the dropwise addition, until the point of raw material toluene disappears with TLC monitoring, after the completion of the reaction, the reaction solution is slowly poured into ice water, and after standing for stratification, The organic layer was washed with water, dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 16.9 g of methyl 2-(2'-methylphenyl)-2-oxoacetate, whose purity was detected by high performance liquid chromatography. 96.5%, yield 91.6%.

[0052] You can make a few more pots according to the above method, as the raw material for the next reaction.

[005...

Embodiment 2

[0065] (1) Synthesis of 2-(2'-methylphenyl)-2-oxomethyl acetate

[0066] Change the amount of anhydrous aluminum trichloride into 13.3g, change the solvent into 92g nitrobenzene, change the amount of monomethyl oxalyl chloride into 18.4g, TLC tracking detects to react completely, other conditions are the same as embodiment 1, obtain 2 -(2'-methylphenyl)-2-oxomethyl acetate 15.7g, the purity detected by high performance liquid chromatography was 95.8%, and the yield was 84.5%.

[0067] You can make a few more pots according to the above method, as the raw material for the next reaction.

[0068] (2) Synthesis of (E)-2-(2'-methylphenyl)-2-methyl oxoacetate-O-methyl ketoxime

[0069] Change the amount of methoxylamine hydrochloride into 16.7g, change the solvent into 142.4g of methyl alcohol, react between 40~45°C, follow up and detect with TLC, react completely in 15 hours, other conditions are the same as embodiment 1, 16.2 g of (E)-2-(2'-methylphenyl)-2-oxoacetic acid methyl...

Embodiment 3

[0080] (1) Synthesis of 2-(2'-methylphenyl)-2-oxomethyl acetate

[0081] Change the amount of anhydrous aluminum trichloride into 26.7g, change the solvent into 46g methylene chloride, change the amount of monomethyl oxalyl chloride into 13.5g, and other conditions are the same as embodiment 1, and obtain 2-(2'-methyl 15.1 g of methyl phenyl)-2-oxoacetate, the purity detected by high performance liquid chromatography was 96.9%, and the yield was 82.2%.

[0082] You can make a few more pots according to the above method, as the raw material for the next reaction.

[0083] (2) Synthesis of (E)-2-(2'-methylphenyl)-2-methyl oxoacetate-O-methyl ketoxime

[0084] Change the amount of methoxylamine hydrochloride into 20.8g, change the solvent into 267.4g butanol, react between 95~100°C, follow up and detect with TLC, react completely in 5 hours, other conditions are the same as embodiment 1, 15.8 g of (E)-2-(2'-methylphenyl)-2-oxoacetic acid methyl ester-O-methyl ketoxime was obtai...

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Abstract

The invention discloses a method for preparing (E,E)-2-[1'-(3'-trifluoromethyl phenyl)-ethyl-imine-oxyl-tolyl]-2-carbonyl methyl acetate-O-ketoxime. The method comprises the following steps of: performing acylation reaction on toluene and methyl oxalyl chloride in the presence of anhydrous aluminum chloride to prepare 2-(2'-methyl phenyl)-2-carbonyl methyl acetate; reacting the 2-(2'-methyl phenyl)-2-carbonyl methyl acetate with methoxy amine hydrochloride to prepare (E)-2-(2'-methyl phenyl)-2-carbonyl methyl acetate-O-methyl ketoxime; and finally performing condensation reaction on the (E)-2-(2'-methyl phenyl)-2-carbonyl methyl acetate-O-methyl ketoxime and m-trifluoromethyl phenyl ethyl ketoxime under the action of alkaline substance to prepare the trifloxystrobin. The method has the advantages of a few reaction steps, simple synthesis process, readily available raw materials, mild reaction conditions, great industrial value and great social and economic benefit.

Description

(1) Technical field [0001] The invention relates to a fungicide trifloxystrobin (E, E)-2-[1'-(3'-trifluoromethylphenyl)-ethyl-imine-oxygen-tolyl]-2-oxoacetic acid Chemical preparation method of methyl ester-O-methanone oxime. (2) Background technology [0002] Trifloxystrobin is a broad-spectrum fungicide, which is effective for strains resistant to 1,4-demethylase inhibitors, benzamides, dicarboxylamines and benzimidazoles. The agent has no cross-resistance, and has the characteristics of high efficiency, broad spectrum, protection, treatment, eradication, penetration, systemic activity, resistance to rain erosion, and long-lasting effect. It has good activity against almost all fungal diseases (Ascomycetes, Basidiomycetes, Oomycetes and Deuteromycetes) such as powdery mildew, rust, blight, net spot, downy mildew, rice blast, etc. . In addition to having special effects on powdery mildew and leaf spot, it has good activity on rust, downy mildew, blight and apple black bl...

Claims

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Application Information

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IPC IPC(8): C07C251/60C07C249/12
Inventor 倪越彪孙炬晖徐俊平
Owner YUEYANG DIPU CHEM TECH
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