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A novel process for the preparation of trifloxystrobin

A new method, the technology of methyl acetate, is applied in a new field for the preparation of trifloxystrobin, which can solve the problems affecting the overall process cost and so on

Active Publication Date: 2018-08-03
GSP CROP SCI PVT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Prior art methods have several difficulties that can affect the overall process cost

Method used

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  • A novel process for the preparation of trifloxystrobin
  • A novel process for the preparation of trifloxystrobin
  • A novel process for the preparation of trifloxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1: Preparation of Hydroxy-O-Methoxy-Acetonitrile (Method A)

[0084]

[0085] 2-Methylbenzaldehyde (120.15gm 1.0mol) was slowly added to the four-neck solution containing water (125mL) and sodium cyanide 49.00gm (1.0mol) at a temperature of 8°C to 10°C under stirring within 0.5 hours in the flask. The solution was prepared by adding sodium cyanide 49.00 gm (1 mol) dropwise to water (125 mL), the mixture was stirred over 30 minutes, during which time the temperature was maintained at -5°C to 5°C, and then the temperature was raised to 8°C ~10°C. After the addition was complete, the reaction mass was stirred for 15 minutes, then 40% sulfuric acid [83 gm sulfuric acid (0.84 mol) in 125 ml of water] was added within three hours, the temperature was maintained between 10° C. and 20° C. and the reaction mixture was stirred for 15 minutes. minute. After the reaction was completed, the product was extracted with dichloroethane and dried over anhydrous sodium sulf...

Embodiment 2

[0086] Example 2: Preparation of Hydroxy-O-Methoxy-Acetonitrile (Method B)

[0087] 2-Methylbenzaldehyde (24.03 gm, 0.2 mol) was added to a solution of concentrated hydrochloric acid (18 ml, 21.6 g, and 0.2 mol) and water (17 ml) in a 200 ml three-necked flask at 0°C. The resulting mixture was cooled to -5°C to yield a slurry of 2-methylbenzaldehyde hydrochloride. Sodium cyanide solution (11.00 g, 0.22 mol) in 40 g of water was added to the reaction mixture dropwise and the mixture was stirred over 30 minutes during which time the temperature was maintained at -5°C to -1°C. During the addition, a yellow solution was obtained after adding about half of the cyanide solution, but formed a slurry again toward the end of the addition. Stirring was continued for one hour after the addition was complete. Hydrochloric acid (1 ml) was added to bring the mixture to pH=7. After the reaction was completed, the product extracted with ethyl acetate was added, and the mixture was warmed...

Embodiment 3

[0088] Example 3: Preparation of Hydroxy-O-Methoxy-Acetonitrile (Method C)

[0089] 2-Methylbenzaldehyde (120.15 gm 1.0 mol) was added to a solution of sodium bisulfite (105 gm 1.0 mol) in water (475 gm) at room temperature, and the temperature was kept below 35°C. Sodium cyanide (49 gm 1.0 mol) was added to the solution in portions, and the temperature was maintained between 25°C and 35°C. The oil phase separates out as the upper layer, and it separates from the lower aqueous layer. The aqueous layer was then extracted with dichloroethane, and the resulting dichloroethane extract was combined with the separated oil layer. The organic layer was dried over anhydrous sodium sulfate, and subjected to vacuum distillation in a hot bath at 40°C to remove dichloroethane. The amount of hydroxy(2-tolyl)acetonitrile obtained remaining was 132 g. The yield of hydroxy(2-tolyl)acetonitrile was 90%.

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Abstract

The present invention relates to a novel process for preparation of methyl (Alpha E)-(Alpha - (methoxyimino)-2-[[[(E)-[1-[3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzeneaceate (Trifloxystrobin) compound of formula (I) in free form or in agro chemically acceptable salt form useful as a pest control agent.The present invention also relates to a novel process for preparation of methyl (2E)-[2-(bromomethyl) phenyl] (methoxyimino) ethanoate of formula (X) intermediate of Trifloxystrobin.

Description

Technical field [0001] The present invention relates to a method for the preparation of formula (I)(αE)-(α-(methoxyimino)-2[[[(E) in free form or in an agrochemically acceptable salt form for use as a pest control agent) - A new method for methyl [1-(3-(trifluoromethyl)phenyl]ethylene]amino]oxy]methyl]phenylacetate (trifloxystrobin). [0002] Background technique [0003] (αE)-(α-(methoxyimino)-2[[[(E)-[1-(3-(trifluoromethyl)phenyl]ethylene]amino]oxy]methyl] Methyl phenylacetate belongs to the methoxyacrylate fungicides. Trifloxystrobin and its preparation method were first described in US5238956. It is most commonly used in bananas, cereals, citrus, coffee, corn, cotton, broad beans, grapes, hops, Nuts, ornamental plants, peanuts, pome fruits, potatoes, rice, small fruits, soybeans, stone fruits, sugar beets, sunflowers, tea, tropical fruits, turf, vegetables and various other crops. [0004] CN103787916A teaches the preparation method of trifloxystrobin. The reaction...

Claims

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Application Information

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IPC IPC(8): C07C249/08C07C249/12C07C251/38C07C251/60
CPCC07C51/08C07C51/29C07C67/20C07C67/22C07C67/313C07C231/06C07C249/08C07C249/12C07C253/08C07C251/60C07C251/48C07C255/36C07C235/34C07C59/48C07C59/84C07C69/732C07C69/738
Inventor 阿吉特·辛格·古杰拉尔海纳尔·V·沙阿巴外史·V·沙阿苏哈什·卡达姆奈尔什·N·贾尼拉温德拉·Y·欣德
Owner GSP CROP SCI PVT
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