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Isoxazoline substituted benzamide derivative as well as preparation method and application thereof

A methyl and fluorinated technology, applied in the direction of botany equipment and methods, applications, biocides, etc.

Pending Publication Date: 2022-06-10
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the biological activity of the above compounds still needs to be further improved

Method used

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  • Isoxazoline substituted benzamide derivative as well as preparation method and application thereof
  • Isoxazoline substituted benzamide derivative as well as preparation method and application thereof
  • Isoxazoline substituted benzamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1: N-(cyanomethyl)-N-cyclopropyl-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroiso Preparation of oxazol-3-yl)-2-methylbenzamide (compound 1)

[0143]

[0144] The first step reaction: the preparation of (Z)-4-((oxime) methyl)-2-methylbenzoate: at room temperature, 26.70g (0.15mol) 4-formyl-2-methyl Methyl benzoate, 12.53g (0.18mol) of hydroxylamine hydrochloride, and 18.45g (0.225mol) of sodium acetate were dissolved in a mixed solution of 75ml of water and 300ml of ethanol. The reaction was stirred for 6 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 25.76 g of the product, with a yield of 89%.

[0145] LC-MS[M+H] + =194.08, [M+Na] + =216.06, [M+K] + = 232.03.

[0146] The second step reaction: the preparation of 1,3-dich...

Embodiment 2

[0156] Example 2: N-(cyanomethyl)--4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3- base)-N-(2,2-difluoroethyl)-2-methylbenzamide (compound 5)

[0157]

[0158] The first step reaction: Preparation of 2-((2,2-difluoroethyl)amino)acetonitrile: 2.43g (0.03mol) 2,2-difluoroethylamine, 3.0g (0.025mol) bromoacetonitrile at room temperature 1. Add 20ml of acetonitrile into the three-necked flask, and stir and react at 60°C for 8 hours. The reaction solution was desolvated under reduced pressure. 60 ml of water were added to the residue, extracted with ethyl acetate (3*20 ml), and the organic phases were combined. Wash with saturated saline. Dry over anhydrous magnesium sulfate. The solvent was removed from the organic phase under reduced pressure to obtain 2.46 g of the product, with a yield of 82%.

[0159] The second step reaction: N-(cyanomethyl)--4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3 -yl)-N-(2,2-difluoroethyl)-2-methyl...

Embodiment 3

[0162] Example 3: N-(cyanomethyl)-N-cyclopropyl-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5 -Preparation of -dihydroisoxazol-3-yl)-2-methylbenzamide (compound 13)

[0163]

[0164]The first step reaction: the preparation of (Z)-4-((oxime) methyl)-2-methylbenzoate: at room temperature, 26.70g (0.15mol) 4-formyl-2-methyl Methyl benzoate, 12.53g (0.18mol) of hydroxylamine hydrochloride, and 18.45g (0.225mol) of sodium acetate were dissolved in a mixed solution of 75ml of water and 300ml of ethanol. The reaction was stirred for 6 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 25.76 g of the product, with a yield of 89%.

[0165] LC-MS[M+H] + =194.08, [M+Na] + =216.06, [M+K] + = 232.03.

[0166] The second step reaction: the preparation of...

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Abstract

The invention belongs to the technical field of insecticides and acaricides, and particularly relates to an isoxazoline substituted benzamide derivative as well as a preparation method and application thereof. The invention specifically provides a compound shown as a formula (I) or a salt thereof. The compound shown as the formula (I) shows good activity on various pests and pest mites 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 insecticides and / or acaricides, and have a relatively good application prospect.

Description

technical field [0001] The invention belongs to the technical field of insecticides and acaricides, and in particular relates to isoxazoline-substituted benzamide derivatives 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 US7951828 discloses the following isoxazoline co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06A01N43/80A01P7/02A01P7/04
CPCC07D231/06A01N43/80
Inventor 唐剑峰迟会伟刘莹吴建挺徐龙祥李文涛李颖
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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