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Diphenylamino-containing thiazole amide compound as well as preparation method and application thereof

A technology based on thiazole amide and diphenylamine, which is applied in the field of thiazole amide compounds and their preparation, achieving good results, simple preparation methods, and novel structures

Pending Publication Date: 2022-04-22
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The main structure of succinate dehydrogenase inhibitors contains amide groups. As a kind of commonly used fungicides, the number of varieties accounts for a considerable proportion of fungicides, and the market share ranks in the forefront. However, these fungicides are used Over time, plant diseases develop resistance to them, and therefore, there is a constant need to invent new and improved compounds and compositions with fungicidal activity to meet the needs of agriculture
[0004] So far, there is no report that the preparation method of thiazole amide compounds containing diphenylamine group is used as agricultural fungicide

Method used

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  • Diphenylamino-containing thiazole amide compound as well as preparation method and application thereof
  • Diphenylamino-containing thiazole amide compound as well as preparation method and application thereof
  • Diphenylamino-containing thiazole amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] N 1 Preparation of -(4-chlorophenyl)-1,2-phenylenediamine (A)

[0028]

[0029] (1)N 1 Preparation of -(4-chlorophenyl)-2-nitroaniline

[0030] Take 2-chloronitrobenzene (10.0mmol) and 4-chloroaniline (15.0mmol) in a single-necked bottle, add potassium carbonate and polyethylene glycol-1000, after the addition is complete, heat up to 185°C, react for 20h, and detect by TLC. After completion of the reaction, cool to room temperature, add ethyl acetate to extract 3 times, combine the organic layers, and wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, precipitate to obtain an oil, and purify by column chromatography to obtain N 1 -(4-Chlorophenyl)-2-nitroaniline, yield 58.5%.

[0031] (2)N 1 Preparation of -(4-chlorophenyl)-1,2-phenylenediamine (A)

[0032] N 1 -(4-Chlorophenyl)-2-nitroaniline (5.0mmol) was dissolved in 75% ethanol (20mL), then ammonium chloride (15.0mmol) and reduced iron powder (15.0mmol) were added, after addition,...

Embodiment 2

[0034] N 1 Preparation of -(4-chlorophenyl)-4-fluorobenzene-1,2-diamine (B):

[0035]

[0036] (1) Preparation of N-(4-chlorophenyl)-5-fluoro-2-nitroaniline

[0037] 2,4-Difluoronitrobenzene (10.0mmol), substituted aniline (15.0mmol) and potassium fluoride (10.0mmol) were stirred in a 100mL round bottom flask at 160°C for 14 hours without solvent. Cool and quench the reaction with water, add ethyl acetate to extract 3 times, combine the organic layers, dry over anhydrous sodium sulfate, filter out anhydrous sodium sulfate, precipitate and dissolve with ethanol, decolorize with activated carbon, remove the activated carbon by suction and recrystallize or use Pure petroleum ether column chromatography gave N-(4-chlorophenyl)-5-fluoro-2-nitroaniline in a yield of 80.6%.

[0038] (2)N 1 Preparation of -(4-chlorophenyl)-4-fluorobenzene-1,2-diamine (B)

[0039] Dissolve N-(4-chlorophenyl)-5-fluoro-2-nitroaniline (5.0mmol) in 75% ethanol (20mL), then add ammonium chloride (15....

Embodiment 3

[0041] Preparation of thiazole amide compound (I-4) containing diphenylamino group

[0042] Add N to the one-necked bottle 1 -(4-Chlorophenyl)-1,2-phenylenediamine (A) (1.0mmol), add 20mL of acetonitrile to dissolve, slowly add 2-methyl-4-trifluoromethylthiazole-5-methanol dropwise at room temperature Chlorine (1.2mmol), after dropping, the temperature was raised to reflux for 3h, monitored by TLC, the reaction was completed, acetonitrile was recovered by precipitation, extracted 3 times with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and suction filtered. The crude product was obtained by precipitation, and the thiazole amide compound (I-4) containing diphenylamino group was obtained by column chromatography. The product characterization data was: white solid, yield 73.2%, m.p.146.5-147.0°C; 1 H NMR (400MHz, CDCl 3 )δ8.59-8.43(m,2H,C 6 h 4 ),7.50(s,1H,NH),7.24(s,3H,CONH+C 6 h 4 ),7.17(t,J=7.6Hz,1H,C 6 h 4 ),7...

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Abstract

The invention belongs to the field of bactericides, and discloses a diphenylamino-containing thiazole amide compound as well as a preparation method and application thereof, the structural formula of the diphenylamino-containing thiazole amide compound is as follows: R is selected from methyl, difluoromethyl and trifluoromethyl; r1 is selected from hydrogen, fluorine, chlorine, bromine and iodine; r2 is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, methoxyl, trifluoromethyl, difluoromethoxyl and trifluoromethoxyl. The compound disclosed by the invention is novel in molecular structure, is a new compound and is distinct in chemical structural characteristics, thiazole and diphenylamine groups in the structural formula are simple and convenient in preparation method, raw materials are easy to obtain, and the compound has relatively high bactericidal activity on rhizoctonia solani and the like and can be used for preventing and treating fungal diseases in agriculture.

Description

technical field [0001] The invention relates to the field of fungicides, in particular to a diphenylamine-containing thiazole amide compound and a preparation method and application thereof. Background technique [0002] Plant diseases are one of the natural disasters that seriously endanger agricultural production. Pesticides, as an important means of preventing pests and weeds and protecting crops, play an irreplaceable and important role in agricultural production. Cucumber wilt, apple ringworm, tomato early blight, peanut brown fungus and wheat head blight are common pathogens in crop growth. Traditional chemical pesticides such as chlorothalonil and azoxystrobin are resistant to long-term use Research and development of new pesticides can increase agricultural production and income. [0003] The main structure of succinate dehydrogenase inhibitors contains amide groups. As a kind of commonly used fungicides, the number of varieties accounts for a considerable proportio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56A01N43/78A01P3/00
CPCC07D277/56A01N43/78
Inventor 闫忠忠
Owner ANHUI UNIV OF SCI & TECH
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