N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof

A technology of dimethylpyrazole carboxamide and benzamide, applied in N-(2-pyridyl)-2-(2,4-dimethylpyrazole carboxamide) benzamide and its preparation It can solve the problems of decreased pesticide use efficiency and easy resistance, and achieve the effect of outstanding antibacterial activity and simple synthesis process

Inactive Publication Date: 2016-07-20
WUHAN INSTITUTE OF TECHNOLOGY
View PDF7 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] With global warming, crop diseases and insect pests are on the rise, and the demand for pesticides is increasing year by year. At the same time, the continuous use of a single variety of pes

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
  • N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof
  • N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof
  • N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of 2-nitro-N-(2-pyridyl)benzamide:

[0034] Add 4.18g (0.025mol) of o-nitrobenzoic acid and 10mL (0.14mol) of thionyl chloride into a 50mL flask, heat to reflux for 6h, evaporate the solvent under reduced pressure to obtain o-nitrobenzoyl chloride for later use. Add 30mL of dehydrated dichloromethane, 5g (0.05mol) of triethylamine and 2.35g (0.025mol) of 2-aminopyridine into a 50mL three-necked flask, and dissolve o-nitrobenzoyl chloride into the dehydrated dichloromethane solution under stirring at 0°C Slowly add it dropwise into a three-necked flask, stir the reaction, and follow the reaction by TLC. After the reaction is completed, dilute with 30 mL of dichloromethane and 25 mL of water, extract the aqueous layer with dehydrated dichloromethane (20 mL×3), combine the organic layers, and wash the organic layer with 1.2 mol / L NaHCO3 aqueous solution was washed until neutral, then washed with saturated brine, dried with anhydrous MgSO4, filtered, and precipita...

Embodiment 2

[0036] Synthesis of 2-nitro-N-(2-pyridyl)benzamide:

[0037] Add 4.18g (0.025mol) of o-nitrobenzoic acid and 20mL (0.28mol) of thionyl chloride into a 50mL flask, heat to reflux for 3h, and distill off excess thionyl chloride under reduced pressure to obtain o-nitrobenzoyl chloride spare. Add 15mL of anhydrous THF, 5g (0.05mol) of triethylamine and 2.35g (0.025mol) of 2-aminopyridine into a 50mL three-necked flask, and slowly dissolve the solution of o-nitrobenzoyl chloride in anhydrous THF under stirring at 0°C. Add dropwise into a three-necked flask, stir the reaction, follow the reaction by TLC, dilute with 30mL ethyl acetate and 25mL water after the reaction is complete, extract the aqueous layer with ethyl acetate (20mL×2), combine the organic layers, and wash the organic layer with 1.2mol / LNaHCO 3 Wash with aqueous solution to neutrality, then wash with saturated brine, anhydrous Na 2 SO 4 Dry, filter, and precipitate under reduced pressure to obtain a crude product...

Embodiment 3

[0039] Synthesis of 2-nitro-N-(2-pyridyl)benzamide:

[0040] Add 4.18g (0.025mol) of o-nitrobenzoic acid and 10mL (0.14mol) of thionyl chloride into a 50mL flask, heat to reflux for 6h, evaporate the solvent under reduced pressure to obtain o-nitrobenzoyl chloride for later use. Add 15mL of anhydrous THF, 5g (0.05mol) triethylamine and 2.35g (0.025mol) of 2-aminopyridine into a 50mL three-necked flask, and slowly drop the anhydrous THF solution of o-nitrobenzoyl chloride into the three-necked flask while stirring at 0°C. In the flask, stir the reaction, follow the reaction by TLC, after the reaction is completed, dilute with 30mL ethyl acetate and 25mL water, extract the aqueous layer with ethyl acetate (20mL×2), combine the organic layers, and use 1.2mol / L NaHCO for the organic layer 3 Wash with aqueous solution to neutrality, then wash with saturated brine, anhydrous Na 2 SO 4 Drying, filtration, and precipitation under reduced pressure gave the crude product, which was re...

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 relates to N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as a preparation thereof and use thereof. A structural formula of the N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide is as shown in the specification. The preparation method comprises the following steps: taking o-nitrobenzoic acid as a starting material, and carrying out amidation to obtain an intermediate 2-nitrobenzamide; then, reducing nitryl into amido by use of iron powder; and finally, enabling the amido to act with the intermediate acyl chloride under the action of triethylamine, thereby acquiring a target compound N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide. The N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide has the beneficial effects that the synthesis process is simple; the acquired compound has outstanding bacteriostatic activity on rice sheath blight fungi (Rhizoctorzia solani), and has a bacteriostasis rate of 72.8% on the rice sheath blight fungi under concentration being 1000 ppm.

Description

technical field [0001] The present invention relates to N-(2-pyridyl)-2-(2,4-dimethylpyrazolecarboxamido)benzamide and its preparation and application. Background technique [0002] With global warming, crop diseases and insect pests are on the rise, and the demand for pesticides is increasing year by year. At the same time, the continuous use of a single variety of pesticides is likely to cause resistance and lead to a decline in the use efficiency of pesticides. Therefore, it is necessary to continuously develop novel structures that act on new target pesticides. [0003] Insecticide phthalamide compounds that act on ryanodine receptors began to be developed in the 1990s, and they were put into use in 2000 and soon achieved great success. When we studied the insecticidal activity of these compounds, we found that some derivatives had certain bactericidal activity. Contents of the invention [0004] The technical problem to be solved by the present invention is to propo...

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
IPC IPC(8): C07D401/12A01N43/56A01P3/00
CPCC07D401/12A01N43/56
Inventor 巨修练颜琦松刘志强
Owner WUHAN INSTITUTE OF TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap