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O-carboxamido benzamide derivative based on ryanodine receptor, and preparation method and application thereof

A technology for o-formamidobenzamide and formamidobenzamide, which is applied in the field of o-formamidobenzamide derivatives and the preparation thereof, and can solve problems such as limited number of varieties

Inactive Publication Date: 2016-06-15
JIANGXI TIANREN ECOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although bisamide insecticides have shown outstanding advantages in terms of activity, pests have shown varying degrees of resistance due to frequent over-application in some areas, and the number of commercialized varieties of this type of insecticides is very limited so far.

Method used

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  • O-carboxamido benzamide derivative based on ryanodine receptor, and preparation method and application thereof
  • O-carboxamido benzamide derivative based on ryanodine receptor, and preparation method and application thereof
  • O-carboxamido benzamide derivative based on ryanodine receptor, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: 3-bromo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-(methoxycarbamoyl)-6-methylphenyl)-1H- Preparation of pyrazole-5-carboxamide (compound I-10)

[0068]

[0069] Compound I-10 can be prepared by the following method, and the specific steps are as follows:

[0070]

[0071] Preparation of intermediate 3-bromo-1-(3-chloro-pyridyl)-1H-pyrazole-5-carboxylic acid III-1:

[0072]

[0073] Preparation of 2-(3-bromo-pyrazol-1-yl)-3-chloropyridine:

[0074] 3-Bromo-1H-pyrazole was dissolved in DMF (80 mL), 2,3-dichloro-pyridine (13.8 g) and potassium carbonate (57.3 g) were added, and the mixture was stirred at 100° C. for 8 hrs. After adding water, the mixture was extracted twice with ethylamine, the combined organic layers were washed twice with water, brine, washed with Na 2 SO 4 Dry and concentrate in vacuo. The residue was purified by column chromatography (propylamine / ethylamine 6:1) to give 7 g of the title compound 2-(3-bromo-pyrazol-1-yl)-3-chloropyr...

Embodiment 2

[0082] Example 2: 3-bromo-N-(4-chloro-2-methyl-6-(carboxycarbamoyl)phenyl)-1-(3,5-dichloropyridin-2-yl)-1H- Preparation of pyrazole-5-carboxamide (compound 1-2)

[0083]

[0084] Compound I-2 can be prepared by the following method, and the specific steps are as follows:

[0085] Preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3,5-dichloropyridine:

[0086]

[0087] Compound I-2 can be prepared by the following method, and the specific steps are as follows:

[0088] Preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3,5-dichloropyridine:

[0089]

[0090] This compound is carried out in the same manner as for the preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine, from 3-bromo-1H-pyrazole and 2,3,5-trichloropyridine to prepare.

[0091] Preparation of 3-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (III-2):

[0092]

[0093] Compound III-2 was prepared from 2-(3-bromo-1H-pyrazol-1-yl)-3,5-dichloropyridine and carbon dioxide using the same method...

Embodiment 3

[0098] Example 3: 3-bromo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-(hydroxycarbamoyl)-6-methylphenyl)-1H-pyrazole -Preparation of 5-formamide (compound 1-9):

[0099]

[0100] Compound I-9 was prepared from intermediate V-1) by the same steps as in Preparation Example 1, wherein the reagent compound VI) was prepared with NH 2 OH·HCl instead of CH 3 ONH 2 • HCl. To 2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4-oxo-4H-benzo[d][1 , 3] Oxazine-6-carbonitrile (V-1) (50 mg, 0.11 mmol) dissolved in CH 3 A solution in CN (5 mL) was added with NH 2 OH·HCl (159.8 mg, 2.3 mmol) and Et 3 N (319.3uL, 2.3mmol), stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated in vacuo and subjected to flash chromatography (dichloromethane:methanol=10:1) to give a colorless solid (15 mg, yield: 28%); 1HNMR (DMSO-d6, 300MHz ), δ: 2.14(s, 3H), 7.36(s, 1H), 7.61-7.65(dd, 1H, J=7.8Hz, J=4.8Hz), 7.75(s, 1H), 8.04(s, 1H) , 8.18-...

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Abstract

The invention provides a series of o-carboxamido benzamide derivatives, and preparation methods and applications thereof. The o-carboxamido benzamide derivatives have the chemical structure general formula represented as the formula I. The invention also discloses: the general formula and the synthetic method of the compounds and an application of the compounds in insecticides, acaricides and bactericides, and a process of preparing the acaricides and bactericides by mixing the compounds with agriculturally acceptable additives or synergists, and also discloses the combination of the compounds with commercial insecticides, acaricides, bactericides, anti-plant-viral agents and plant activators to prevent and treat diseases, pest damage, mite damage and viral diseases in the fields of agriculture, forestry and horticulture.

Description

[0001] The application date is December 5, 2013, the application number is 201310643995.9, and the application name is a class of o-formamidobenzamide derivatives based on Yuniding receptors and their preparation methods and uses. The applicant is Jiangxi Tian Divisional application for invention patent of Human Ecology Co., Ltd. technical field [0002] The present invention relates to a class of derivatives based on the saliva receptor, in particular to a class of o-formamidobenzamide derivatives and a preparation method and application thereof. Background technique [0003] Pest attack on growing crops as well as stored crops can lead to significantly lower yields, which in turn lead to increased production costs. Pest control is important in forestry, greenhouse crops, ornamental plants, crop seedlings, stored food and fiber products, livestock, household, lawn, wood products, and sanitation. The new ultra-high-efficiency insecticide bisamide has a novel structure, a un...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/40A01P7/04A01P7/02A01P3/00A01P1/00
CPCC07D401/04A01N43/40
Inventor 梁小文
Owner JIANGXI TIANREN ECOLOGY
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