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A kind of isoxazoline substituted benzamide derivatives and its preparation method and application

A technology of hydroxylamine and compounds, applied in the field of isoxazoline-substituted benzamide derivatives and their preparation

Active Publication Date: 2021-10-29
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 biological activity of the above compounds still needs to be further improved

Method used

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  • A kind of isoxazoline substituted benzamide derivatives and its preparation method and application
  • A kind of isoxazoline substituted benzamide derivatives and its preparation method and application
  • A kind of isoxazoline substituted benzamide derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Example 1: N-((6-chloropyridin-3-yl)methyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)- Preparation of 4,5-dihydroisoxazol-3-yl)-2-methylbenzamide (Compound 1)

[0122]

[0123] The first step reaction: the preparation of (Z)-4-((oxime)methyl)-2-methylbenzoate: at room temperature, 17.80g (0.1mol) 4-formyl-2-methyl Methyl benzoate, 8.35g (0.12mol) of hydroxylamine hydrochloride, and 12.30g (0.15mol) of sodium acetate were dissolved in a mixed solution of 50ml of water and 200ml of ethanol. The reaction was stirred for 5 hours. The reaction mixture was concentrated, diluted with ethyl acetate and aqueous sodium hydroxide (2M), and the phases were separated. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Suction filtration and drying yielded 17.76 g of the product with a yield of 92%.

[0124] LC-MS[M+H] + =194.08, [M+Na] + =216.06, [M+K] + = 232.03.

[0125] The second step reaction: the preparation of 1,3-...

Embodiment 2

[0134] Example 2: N-((6-chloropyridin-3-yl)methyl)-2-methyl-4-(5-(trifluoromethyl)-5-(3,4,5-trifluorobenzene base)-4,5-dihydroisoxazol-3-yl)benzamide (compound 2)

[0135]

[0136] The first step reaction: Preparation of 1,2,3-trifluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene: 3.52g (0.02mol ) 3,4,5-trifluorophenylboronic acid, 6.90g (0.05mol) of potassium carbonate, 0.35g (0.0005mol) of bis(triphenylphosphine)palladium chloride and 80ml of toluene were added into a three-necked flask and stirred. To the above mixture was added 5.25 g (0.03 mol) of 2-bromo-3,3,3-trifluoroprop-1-ene in portions. After the addition was complete, the reaction was stirred at 80°C for 9 hours. The reaction solution was cooled to room temperature, and 50 ml of water was added to the above reaction solution. Phase. The aqueous layer was extracted with toluene (2*30ml), and the organic phases were combined. Wash with saturated saline. Dry over anhydrous sodium sulfate and filter. The filtra...

Embodiment 3

[0145] Example 3: N-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-4-(5-(3,5-dichloro-4-fluorophenyl)- Preparation of 5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide (Compound 9)

[0146]

[0147] At 0°C, 1.75g ​​(0.004mol) of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-2-methylbenzoic acid, 1.03g (0.008mol) di(isopropyl)ethylamine, 2.29g (0.0044mol) benzotriazol-1-yl-oxytripyrrolidine hexafluorophosphate Phosphorus was successively dissolved in 30ml of dichloromethane. The reaction mixture was stirred for 2 hours. To the above solution was added 1.01 g (0.0048 mol) of 3-chloro-5(trifluoromethyl)pyridin-2-yl)methanamine at room temperature. Stirring was continued for 15 hours at room temperature. 20ml of water was added to the reaction system, and the phases were separated. The aqueous phase was extracted twice with dichloromethane. The organic phases were combined, washed with saturated brine, and dried over ...

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Abstract

The invention belongs to the technical field of insecticides and acaricides, and in particular relates to an isoxazoline-substituted benzamide derivative and a preparation method and application thereof. The present invention specifically provides a compound represented by the following formula (I) or a salt thereof, and the compound represented by the formula (I) shows good activity against various pests and harmful mites in agriculture or other fields. Moreover, these compounds can obtain good control effects at very low doses, so they can be used to prepare insecticides and / or acaricides, and have good application prospects.

Description

technical field [0001] The invention belongs to the technical field of insecticides and acaricides, and in particular relates to an isoxazoline-substituted benzamide derivative and a preparation method and application thereof. Background technique [0002] Insecticides and acaricides have played an extremely important role in increasing agricultural production and solving human food problems. As the safety and environmental impact of chemical substances are increasingly required, the development of safer pest control agents has been desired. Moreover, due to the perennial use of pest control agents such as insecticides and acaricides, pests gradually develop resistance to these biological control agents, resulting in unsatisfactory control effects. Therefore, it is the future development trend to develop pest control agents with excellent performances such as safety, control effect and residual effect. [0003] Patent document WO2005085216 discloses the following isoxazoli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12A01N43/80A01P7/02A01P7/04A01P5/00
CPCC07D413/12A01N43/80A01P7/02A01P7/04
Inventor 唐剑峰迟会伟吴建挺于斌徐龙祥赵宝修杨绎李冬蓉
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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