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

Preparation and bactericidal activity of N-pyridyl-substituted thiazole methanamide compounds

A technology based on thiazole carboxamide and pyridyl, which is applied in the fields of fungicides, organic chemistry, biocides, etc.

Inactive Publication Date: 2013-06-19
天津都创科技有限公司
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, thiazopyridine compounds have not been reported

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
  • Preparation and bactericidal activity of N-pyridyl-substituted thiazole methanamide compounds
  • Preparation and bactericidal activity of N-pyridyl-substituted thiazole methanamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Add 0.01mol of 2-methyl-4-trifluoromethylthiazole carboxylic acid chloride, 30ml of toluene, 0.01mol of 3-chloro-5-trifluoromethyl-2-aminopyridine, 0.01g of triethylamine into the three-necked flask, Heat to reflux, react for 8 hours, evaporate to remove the solvent, add 20ml of water and stir for 30min, the aqueous phase is extracted with ethyl acetate, and the organic phase is extracted with 10% NaHCO 3 , water, brine, and spin-dried to obtain a crude product. The resulting solid was separated by recrystallization to obtain the target compound a with a yield of 73.5%. Compound a is a white solid powder. Melting point: 128-129°C. MS: 390.2 (m / z, M+1). 1 H NMR (500MHz, CDCl 3 ): 2.786 (s, 3H, CH 3 ), 8.005-8.009 (d, 1H, Py-H), 8.592 (s.1H, Py-H), 8.613 (s, 1H, NH).

Embodiment 2

[0014] Add 0.01mol of 2-methyl-4-trifluoromethylthiazoleformyl chloride, 30ml of toluene, 0.01mol of 3-chloro-2-aminopyridine, 0.01g of triethylamine into the three-neck flask, heat to reflux, and react for 8 hours , evaporated to remove the solvent, added 20ml of water and stirred for 30min, the aqueous phase was extracted with ethyl acetate, and the organic phase was extracted with 10% NaHCO 3 , water, brine, and spin-dried to obtain a crude product. The resulting solid was separated by recrystallization to obtain the target compound c with a yield of 68.4%. Compound c is a white solid powder. Melting point: 133-134°C. MS: 322.1 (m / z, M+1). 1 H NMR (500MHz, CDCl 3 ): 2.770 (s, 3H, CH 3 ), 7.128-7.154 (m, 1H, Py-H), 7.786-7.806 (m, 1H, Py-H), 8.327-8.335 (m, 1H, Py-H), 9.499 (s, 1H, NH).

Embodiment 3

[0016] Add 0.01mol of 2-methyl-4-trifluoromethylthiazoleformyl chloride, 30ml of toluene, 0.01mol of 4-chloro-2-aminopyridine, 0.01g of triethylamine into the three-neck flask, heat to reflux, and react for 8 hours , evaporated to remove the solvent, added 20ml of water and stirred for 30min, the aqueous phase was extracted with ethyl acetate, and the organic phase was extracted with 10% NaHCO 3 , washed with water, brine, and spin-dried to obtain a crude product, and the resulting solid was separated by column chromatography to obtain the target compound d with a yield of 72.5%. Compound d is a gray solid powder. Melting point: 186-187°C. MS: 322.2 (m / z, M+1). 1 H NMR (500MHz, CDCl 3 ): 2.758 (s, 3H, CH 3 ), 7.064-7.089 (m, 1H, Py-H), 7.753-7.787 (m, 1H, Py-H), 8.048-8.058 (d, 1H, Py-H), 8.247-8.264 (d, 1H, Py-H -H), 9.487 (s, 1H, NH).

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 preparation and bactericidal activity of N-pyridyl-substituted thiazole methanamide compounds a-e. The N-pyridyl-substituted thiazole methanamide compounds are synthesized from 2-methyl-4-trifluoromethyl thiazole methanamide and substituted amino-pyridine. According to results of bactericidal activity tests of the N-pyridyl-substituted thiazole methanamide compounds, the target compounds show good inhibitory activity on rice sheath blight fungus, and the compound a with best performance has an inhibition rate of 91.78% under the condition of a mass concentration of 500 mg / L.

Description

technical field [0001] The invention relates to a preparation method and bactericidal activity of N-pyridyl substituted thiazole carboxamide compounds, belonging to a class of new pesticides that can be used as bactericides. Background technique [0002] In recent years, 80% of the newly developed pesticide varieties are heterocyclic compounds, among which nitrogen-containing heterocyclic rings are the most important. Thiazole compounds have been extensively studied because of their good biological activity, high efficiency and low toxicity, and the application of pyridine compounds in pesticides has also increased rapidly since the 1980s. But thiazopyridine compounds have not been reported yet. In order to find a broad-spectrum fungicide with better activity, high efficiency and low toxicity, 2-methyl-4-trifluoromethylthiazole carboxyl chloride and substituted aminopyridine were selected to synthesize compounds a-e. Contents of the invention [0003] The purpose of the ...

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): C07D417/12A01P3/00
Inventor 李巍肖捷尤旭东张耀强
Owner 天津都创科技有限公司