Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of pyridylpyrazole-4-carboxamide compound based on sulfur-containing functional group and its preparation method and application

A technology of pyridylpyrazoles and carboxamides, which is applied in the field of pyridylpyrazole-4-carboxamides and their preparation, and achieves the effects of easy operation, simple method and good insecticidal activity

Active Publication Date: 2021-09-17
江苏耘农化工有限公司
View PDF14 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional pesticides in the past can no longer meet the development needs of today's society, and the discovery of new broad-spectrum pesticides with high efficiency, low toxicity, low residue, and environmental friendliness is an urgent task for scientific researchers.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of pyridylpyrazole-4-carboxamide compound based on sulfur-containing functional group and its preparation method and application
  • A kind of pyridylpyrazole-4-carboxamide compound based on sulfur-containing functional group and its preparation method and application
  • A kind of pyridylpyrazole-4-carboxamide compound based on sulfur-containing functional group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: 3-bromo-N-(4-chloro-2-methyl-6-(2-(2-(methylthio)acetyl)hydrazinecarbonyl)phenyl)-1-(3-chloropyridine Preparation of -2-yl)-1H-pyrazole-5-carboxamide

[0067]

[0068] In a 100mL single-necked bottle, the intermediate 3-bromo-N-(4-chloro-2-(hydrazinecarbonyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H- Pyrazole-5-carboxamide (0.48 g, 1 mmol), methylthioacetic acid (0.10 g, 1.0 mmol) and TBTU (0.35 g, 1.1 mmol) were dissolved in 20 mL of N,N-dimethylformamide (DMF) , stirred at room temperature for 15min, then added TEA (0.30g, 3.0mmol) and continued to stir, reacted for 3h, followed by TLC spot plate, after the raw material point disappeared, pour the reaction solution into 500mL saturated sodium chloride solution, stir for 0.5h, and dissolve the solid Filter, dry, and purify by column chromatography.

Embodiment 2

[0069] Example 2: 3-bromo-N-(4-chloro-2-methyl-6-(2-(2-(methylsulfinyl)acetyl)hydrazinecarbonyl)phenyl)-1-(3- Preparation of chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

[0070]

[0071] In a 100mL single-necked bottle, the intermediate 3-bromo-N-(4-chloro-2-methyl-6-(2-(2-(methylthio)acetyl)hydrazinecarbonyl)phenyl)-1- (3-Chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (0.57g, 1mmol), m-chloroperoxybenzoic acid (MCPBA) (0.21g, 1.0 mmol) was dissolved in 20mL dichloro In methane (DCM), stir under ice bath for 15min, then add sodium bicarbonate (0.25g, 3mmol) and continue to stir, react for 3h, TCL dot plate tracking, after the raw material point disappears, the reaction solution is dried under reduced pressure, column chromatography Purify.

Embodiment 3

[0072] Example 3: 3-bromo-N-(4-chloro-2-methyl-6-(2-(2-(methylsulfonyl)acetyl)hydrazinecarbonyl)phenyl)-1-(3-chloro Preparation of pyridin-2-yl)-1H-pyrazole-5-carboxamide

[0073]

[0074] In a 100mL single-necked bottle, the intermediate 3-bromo-N-(4-chloro-2-methyl-6-(2-(2-(methylthio)acetyl)hydrazinecarbonyl)phenyl)-1- (3-Chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (0.57g, 1mmol), m-chloroperoxybenzoic acid (MCPBA) (0.51g, 2.5mmol) was dissolved in 20mL dichloromethane ( DCM), stirred at room temperature for 15 min, then added sodium bicarbonate (0.25 g, 3 mmol) and continued to stir, reacted for 3 h, followed by TCL spot plate, after the raw material point disappeared, the reaction solution was dried under reduced pressure, and purified by column chromatography.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a pyridylpyrazole-4-carboxamide compound based on a sulfur-containing functional group and its preparation method and application. The benzamide compound is further structurally modified, and the fatty acid amide is latent in 1,3,4 -Oxadiazole, bishydrazide, and through the method of active substructure splicing, connect the sulfur-containing functional group to obtain a series of pyridylpyrazole-4-carboxamide compounds with sulfur-containing functional groups that have not been reported in the literature. This type of compound has a large change from the lead chlorantraniliprole, and has excellent preventive effects on harmful insects. It can be used as the active ingredient of various crop insecticides in agriculture and horticulture, and has the advantages of high efficiency, low toxicity, and environmental friendliness. .

Description

technical field [0001] The invention relates to the field of pesticides and insecticides, in particular to a pyridinepyrazole-4-carboxamide compound based on a sulfur-containing functional group, a preparation method and application thereof. [0002] technical background [0003] With the wide application of pesticides, people's understanding of pesticides is getting deeper and deeper. The continuous progress and development of society has prompted profound changes in the concept of pesticides. The traditional pesticides in the past can no longer meet the development needs of today's society, and the discovery of new broad-spectrum pesticides with high efficiency, low toxicity, low residue, and environmental friendliness is an urgent task for scientific researchers. [0004] Formanilide compounds are effective insecticides developed in recent years against Lepidoptera pests. A new type of compound that targets ryanodine receptors was developed by DuPont in 2000. Such compo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C07D401/04A01N43/56A01N43/824A01P7/04
Inventor 刘睿徐涛朱红军宋广亮李楠陈永国
Owner 江苏耘农化工有限公司