Pyrazole amide compound and application thereof

A technology of pyrazole amides and compounds, which is applied in the field of fungicides and can solve problems such as structural pyrazole amides that have not been reported.

Active Publication Date: 2015-05-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the structure of the pyrazole amide compound as shown in the general formula I of the present invention has not been reported

Method used

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  • Pyrazole amide compound and application thereof
  • Pyrazole amide compound and application thereof
  • Pyrazole amide compound and application thereof

Examples

Experimental program
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Synthetic example

[0038] The following synthesis examples and biological activity measurement examples can be used to further illustrate the present invention, but are not meant to limit the present invention.

[0039] synthetic example

example 1

[0040] The preparation of example 1 compound 1:

[0041]

[0042] Add m-isopropoxyaniline (130 mg, 0.85 mmol, synthetic method refer to Bioorganic & Medicinal Chemistry, 2012, 20(3): 1213-1221), triethylamine (90 mg, 0.85 mmol) and 10 1 ml of dichloromethane, add 1-methyl-3-difluoromethylpyrazole-4-carbonyl chloride (170 mg, 0.85 mmol, synthetic method refer to example 6 in patent WO2008053043A1) dropwise under stirring at room temperature solution 10 ml. After dropping, the reaction was carried out at room temperature, and the reaction was completed after 3 hours. The reaction solution was poured into 30 ml of water, and the organic layer was taken. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1:2) to obtain 180 mg of compound 1 wit...

example 2

[0043] The preparation of example 2 compound 4:

[0044] (1) Synthesis of 1-(2-butoxy)-2-methyl-3-nitrobenzene

[0045]

[0046] To a DMF solution of 2-methyl-3-nitrophenol (2.00 g, 13.06 mmol) was added 2-bromo-sec-butane (2.14 g, 15.17 mmol) and potassium carbonate (2.16 g, 15.17 mmol), at The reaction was carried out at 90° C. for 2 hours. The reaction was stopped, ethyl acetate and water were added for extraction, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to dryness, and the residue was purified by column chromatography (ethyl acetate:petroleum ether=1:100) to obtain 1.65 g of solid.

[0047] (2) Synthesis of 2-methyl-3-(2-butoxy)aniline

[0048]

[0049] Add hydrazine hydrate (5.97 g, content: 40%, 47.76 mmol) to a solution of 1-(2-butoxy)-2-methyl-3-nitrobenzene (1.25 g, 5.97 mmol) in ethanol and 0.06 g of 10% palladium carbon, refluxed for two hours. Stop the reaction, filter, add...

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PUM

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Abstract

Disclosed is a pyrazole amide compound as represented by general formula I, wherein, R1 is selected from hydrogen, C1-C4 alkyl, C2-C6 alkenyl, and C1-C6 alkyl; and R2 and R3 can be the same or different, and are respectively and independently selected from the C1-C6 alkyl. The general formula I compound has an excellent bactericidal activity, and can be used to prevent and control fungal diseases.

Description

technical field [0001] The invention belongs to the field of fungicides. It relates to a pyrazole amide compound and its bactericidal application. Background technique [0002] Since diseases develop resistance to fungicides after a period of use, there is a constant need to invent new and improved compounds and compositions with fungicidal activity. [0003] The fungicidal activity of 4-difluoromethylpyrazole amides has been reported. For example, the Journal of Pesticide Science, 2011, 13(6):576-580 disclosed compound KC (compound 7g in the article) and its fungicidal activity. [0004] [0005] In the prior art, no pyrazole amide compound with a structure as shown in the general formula I of the present invention has been reported. Contents of the invention [0006] The object of the present invention is to provide a pyrazole amide compound with novel structure and better bactericidal activity, which can be applied to the prevention and control of agricultural dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14A01N43/56A01P3/00
CPCA01N43/56C07D231/14
Inventor 吕亮李玉钢周继中吴沙沙王斌刘鹏杨辉斌李斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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