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

N-substituted-2-(2-hydroxybenzyl) glycine amide compound and preparing method and application thereof

A technology of aminoacetamide and hydroxybenzyl, applied in the field of pesticides

Active Publication Date: 2016-04-20
HUNAN UNIV OF SCI & TECH
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no literature report on N-substituted-2-(2-hydroxybenzyl) aminoacetamide compounds

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-substituted-2-(2-hydroxybenzyl) glycine amide compound and preparing method and application thereof
  • N-substituted-2-(2-hydroxybenzyl) glycine amide compound and preparing method and application thereof
  • N-substituted-2-(2-hydroxybenzyl) glycine amide compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of N-benzyl-2-(2-hydroxybenzyl)aminoacetamide.

[0042] In a 150 mL round bottom flask with reflux condenser and desiccator, add 4.560 g (20 mmol) of N-benzyl-2-bromoacetamide, 2.953 g (24 mmol) of 2-(aminomethyl)phenol, and anhydrous carbonic acid Potassium 3.312g (24mmol), 50mL DMF and THF mixed solvent (V:V=1:1), heated to 65°C and stirred for 3h, followed by TLC plate detection. After the reaction, the solvent was removed under reduced pressure, 40 mL of water was added, and extraction was performed with ethyl acetate (50 mL×3 times). The organic layers were combined and washed with water (40 mL×2 times) and saturated brine (40 mL×2 times) in turn. Drying with anhydrous sodium sulfate, filtering with suction, and concentrating under reduced pressure to obtain a crude product, which is separated by column chromatography to obtain a white solid; mp 107.6-108.4°C, yield 68.7%.

[0043] 1 HNMR(500MHz, CDCl 3 )δ: 7.33-7.30 (m, 2H), 7.25-7.22 (m, 2H), 7.1...

Embodiment 2

[0046] Example 2: Synthesis of N-(2-methylbenzyl)-2-(2-hydroxybenzyl)aminoacetamide.

[0047] In a 150 mL round bottom flask with reflux condenser and desiccator, 4.840 g (20 mmol) of N-(2-methylbenzyl)-2-bromoacetamide and 2.953 g of 2-(aminomethyl)phenol were added. 24mmol), 3.312g (24mmol) of anhydrous potassium carbonate, 50mL of a mixed solvent of DMF and THF (V:V=1:1), heated to 65°C and stirred for 3h, followed by TLC plate detection. After the reaction, the solvent was removed under reduced pressure, 40 mL of water was added, and extraction was performed with ethyl acetate (50 mL×3 times). The organic layers were combined and washed with water (40 mL×2 times) and saturated brine (40 mL×2 times) in turn. Drying with anhydrous sodium sulfate, filtering with suction, and concentrating under reduced pressure to obtain a crude product, which is separated by column chromatography to obtain a white solid; mp 142.2-143.8°C, yield 64.4%.

[0048] 1 HNMR(500MHz, CDCl 3 )δ:7.11(t,J=7...

Embodiment 3

[0051] Example 3: Synthesis of N-(4-methylbenzyl)-2-(2-hydroxybenzyl)aminoacetamide.

[0052] In a 150 mL round bottom flask with reflux condenser and desiccator, 4.840 g (20 mmol) of N-(4-methylbenzyl)-2-bromoacetamide and 2.953 g of 2-(aminomethyl)phenol were added. 24mmol), 3.312g (24mmol) of anhydrous potassium carbonate, 50mL of a mixed solvent of DMF and THF (V:V=1:1), heated to 65°C and stirred for 3h, followed by TLC plate detection. After the reaction, the solvent was removed under reduced pressure, 40 mL of water was added, and extraction was performed with ethyl acetate (50 mL×3 times). The organic layers were combined and washed with water (40 mL×2 times) and saturated brine (40 mL×2 times) in turn. Drying with anhydrous sodium sulfate, filtering with suction, and concentrating under reduced pressure to obtain a crude product, which is separated by column chromatography to obtain a white solid; mp 122.6-123.5°C, yield 67.2%.

[0053] 1 HNMR(500MHz, CDCl 3 )δ: 7.28 (s, ...

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 an N-substituted-2-(2-hydroxybenzyl) glycine amide compound as shown in the general formula (I) and a preparing method thereof. In the general formula (I), R1 is phenyl, C1-C3 alkyl phenyl, C1-C3 alkoxy phenyl, phenyl C1-C3 alkylidene, C1-C3 alkyl phenyl C1-C3 alkylidene, or C1-C3 alkoxy phenyl C1-C3 alkylidene. The compound has high bactericidal activity on crop diseases and is suitable for serving as pesticide.

Description

Technical field [0001] The invention relates to the synthesis of a novel N-substituted-2-(2-hydroxybenzyl)aminoacetamide compound and its bactericidal activity, belonging to the field of pesticides Background technique [0002] Amide compounds are a very important class of active substances, which have been widely used in agricultural sterilization. As early as 1969, since the United States Lililuo Company developed the amide fungicide rustling, it has occupied a very important position in the world pesticide market. In recent years, the research on amide fungicides has received increasing attention. In 2002, Elebe et al. reported that the substituted pyrazole amide compounds had a 94% control effect against Sclerotium hordei and 100%; Hu Liming et al. reported a pyridine-4-carboxamide compound in 2003. The bactericidal activity test showed that its inhibitory rate against Rhizoctonia solani was up to 93%; in 2009, Xu et al. reported that a class of thiazole-4-carboxamide 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 Applications(China)
IPC IPC(8): C07C237/06C07C237/08C07C231/12A01N37/18A01N37/22A01N37/24A01P3/00
CPCA01N37/18A01N37/22A01N37/24C07C231/12C07C237/06C07C237/08
Inventor 唐子龙李新兴齐永存谭经照张少伟彭丽芬
Owner HUNAN UNIV OF SCI & TECH