Pyridine biphenyl compound containing isoxazoline as well as preparation method and application of pyridine biphenyl compound

A kind of technology of compound and solvate, applied in the field of pyridine biphenyl compounds of isoxazoline and preparation thereof, can solve problems such as satisfactory herbicidal performance and the like

Active Publication Date: 2022-06-21
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the herbicidal properties of these known compounds against harmful plants are not always satisfactory

Method used

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  • Pyridine biphenyl compound containing isoxazoline as well as preparation method and application of pyridine biphenyl compound
  • Pyridine biphenyl compound containing isoxazoline as well as preparation method and application of pyridine biphenyl compound
  • Pyridine biphenyl compound containing isoxazoline as well as preparation method and application of pyridine biphenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0213] Example 1: Ethyl 3-(2-chloro-4-fluoro-5-(5-(trifluoromethyl)pyridin-2-yl)phenyl)-5-methyl-4,5-dihydroiso Preparation of oxazole-5-carboxylate (compound 3)

[0214]

[0215] The first reaction: the preparation of 2-chloro-4-fluoro-5-(5-(trifluoromethyl)pyridin-2-yl)benzaldehyde: under nitrogen protection, 3.03g (0.015mol) (4- Chloro-2-fluoro-5-formylphenyl)boronic acid, 6.21g (0.045mol) potassium carbonate, 0.52g (0.00045mol) tetrakis (triphenylphosphine) palladium, 60ml tetrahydrofuran, 30ml water were added to the there-necked flask and stirred . To the above mixture was added portionwise 3.27 g (0.018 mol) of 2-chloro-5-(trifluoromethyl)pyridine. After the addition was completed, the reaction was stirred at 60°C for 8 hours. The reaction solution was cooled to room temperature. Desolvate under reduced pressure. The residue was extracted with ethyl acetate (2*20ml) and the organic phases were combined. Wash once. Wash once with saturated salt water. Dry over...

Embodiment 2

[0222] Example 2: Methyl 3-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4-fluorophenyl)-5-methyl-4,5 - Preparation of dihydroisoxazole-5-carboxylate (compound 122)

[0223]

[0224]The first step reaction: preparation of 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4-fluorobenzaldehyde: under nitrogen protection, 3.03g (0.015mol ) (4-chloro-2-fluoro-5-formylphenyl)boronic acid, 6.21g (0.045mol) potassium carbonate, 0.52g (0.00045mol) tetrakis(triphenylphosphine)palladium, 60ml tetrahydrofuran, 30ml water were added to the Stir in a three-necked bottle. To the above mixture was added portionwise 3.89 g (0.018 mol) of 2,3-dichloro-5-(trifluoromethyl)pyridine. After the addition was completed, the reaction was stirred at 60°C for 8 hours. The reaction solution was cooled to room temperature. Desolvate under reduced pressure. The residue was extracted with ethyl acetate (2*20ml) and the organic phases were combined. Wash once. Wash once with saturated ...

Embodiment 3

[0231] Example 3: Ethyl 3-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4-fluorophenyl)-5-methyl-4,5 - Preparation of dihydroisoxazole-5-carboxylate (compound 123)

[0232]

[0233] At room temperature, 1.77g (0.005mol) 2-chloro-5-(3-chloro-5-trifluoromethyl)pyridin-2-yl)-4-fluorobenzaldehyde oxime, 1.01g (0.0075mol) N- Chlorosuccinimide and 10 ml of N,N-dimethylformamide were added to the three-necked flask, and the reaction was stirred at 40° C. for 2 hours. The reaction solution was cooled to room temperature, 0.68g (0.006mol) of ethyl methacrylate, 0.76g (0.0075mol) of triethylamine in 2ml of N,N-dimethylformamide solution were added to the above mixture, and the mixture was stirred at room temperature for 5 hours . The reaction mixture was diluted with water and ethyl acetate and the phases were separated. The aqueous phase was extracted with ethyl acetate (2*20ml) and the organic phases were combined. The organic phase was washed twice with water and once...

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Abstract

The invention belongs to the technical field of herbicides, and particularly relates to an isoxazoline pyridine biphenyl compound as well as a preparation method and application thereof. The invention specifically provides a compound shown in the following formula (I) or a salt thereof. The compound shown in the formula (I) shows good activity on various harmful weeds in agriculture or other fields. Moreover, the compounds can obtain a very good prevention and treatment effect at a very low dosage, so that the compounds can be used for preparing herbicides and have a relatively good application prospect.

Description

technical field [0001] The invention belongs to the technical field of agricultural herbicides, in particular to a pyridine biphenyl compound of isoxazoline and a preparation method and application thereof. Background technique [0002] Harmful weeds in farmland are the enemy in agricultural production. According to statistics, crops all over the world lose an average of 12% of their output due to weed damage every year. Therefore, weed control is an important link to achieve efficient agriculture. Despite the variety of herbicides on the market, due to the continuous expansion of the market, the increasing resistance of weeds in recent years, and the increasing emphasis on environmental protection, people still need to constantly develop new high-efficiency and safe new varieties of herbicides . [0003] Patent document WO2014048827 discloses an isoxazoline-containing compound CK as shown below 1 (Compound No. 1.1.1): [0004] [0005] However, the herbicidal properti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D413/14A01N43/80A01P13/00
CPCC07D413/10C07D413/14A01N43/80A01P13/00C07D413/04A01N43/00C07D261/02C07D261/08
Inventor 唐剑峰迟会伟赵宝修吴建挺袁雪赵士胜刘立龙
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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