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Disubstituted pyrazolyl carboxanilides

A kind of technology of pyrazolyl carboxanilide and compound, which is applied in the application field of preventing and controlling harmful microorganisms, and can solve problems such as unsatisfactory activity

Inactive Publication Date: 2005-07-27
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compounds described in these publications have good activity; however, their activity is sometimes unsatisfactory at low application rates

Method used

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  • Disubstituted pyrazolyl carboxanilides
  • Disubstituted pyrazolyl carboxanilides
  • Disubstituted pyrazolyl carboxanilides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0325]

[0326] Method a)

[0327] 0.333g (1.3mmol) 3',4'-dichloro-3-fluoro-1,1'-biphenyl-2-amine and 0.33g (1.56mmol) 1-methyl-3-(trifluoromethyl )-1H-pyrazole-4-carbonyl chloride was dissolved in 6ml of tetrahydrofuran, and 0.36ml (2.6mmol) of triethylamine was added. The reaction solution was stirred at 60°C for 16 hours. For work-up, the mixture was concentrated and the residue was purified by silica gel chromatography, eluting with cyclohexane / ethyl acetate.

[0328] 0.39 g (yield 72% of theory) of N-(3',4'-dichloro-3-fluoro-1,1'-biphenyl-2-yl)-1-methyl-3- (Trifluoromethyl)-1H-pyrazole-4-carboxamide with logP (pH2.3) = 3.10.

Embodiment 2

[0330]

[0331] Method b)

[0332] Oxygen was driven off, and under an argon atmosphere, 0.256 g (0.7 mmol) of N-(2-bromo-6-fluorophenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4 -Formamide and 0.12 g (0.77 mmol) of 3-chloro-4-fluorophenylboronic acid are suspended in a mixture of 8 ml of toluene, 1.5 ml of ethanol and 5.25 ml of saturated sodium carbonate solution. To the reaction mixture was added a catalytic amount (0.01-0.3 equiv) of tetrakis(triphenylphosphine)palladium(0), and the mixture was heated at 100° C. for 1 hour under an argon atmosphere. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate. The combined organic phases are concentrated and the residue is purified by silica gel chromatography, eluting with cyclohexane / ethyl acetate (1:1).

[0333] 0.27 g (yield 96% of theory) of N-(3'-chloro-3,4'-difluoro-1,1'-biphenyl-2-yl)-1-methyl-3- (Trifluoroethyl)-1H-pyrazole-4-carboxamide, logP(pH2.3)=3.04.

[0334] Following ...

Embodiment (III-1

[0339]

[0340] method d)

[0341] Oxygen was driven off, and under an argon atmosphere, 51.2 g (0.268 mol) of 3,4-dichlorophenylboronic acid and 42.5 g (0.223 mol) of 2-bromo-6-fluoroaniline were suspended in 300 ml of toluene, 30 ml of ethanol and 220 ml of saturated in a mixture of sodium carbonate solution. To the reaction mixture was added 2.6 g of tetrakis(triphenylphosphine)palladium(0), and the mixture was heated at 80° C. for 12 hours. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate. The combined organic phases are concentrated and the residue is purified by silica gel chromatography, eluting with cyclohexane / ethyl acetate (3:1).

[0342] 37.4 g (yield 65% of theory) of 3',4'-dichloro-3-fluoro-1,1'-biphenyl-2-amine with logP (pH 2.3)=4.09 are obtained.

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Abstract

The invention relates to novel pyrazolyl carboxanilides of formula (I), in which R, R1, R2 and R3 are defined as per the description, to several methods for producing said substances and to the use thereof for combating undesired micro-organisms. The invention also relates to novel intermediate products and to the production of the same.

Description

Technical field [0001] The present invention relates to new pyrazolyl carboxanilide compounds (carboxanilides), various methods for preparing the compounds, and the use of the compounds in preventing and controlling harmful microorganisms in crop protection and material protection. Background technique [0002] A number of carboxanilide compounds are known to have fungicidal activity (see for example EP0545099 and JP 9132567). The compounds described in these publications have good activity; however, at low application rates their activity is sometimes unsatisfactory. Contents of the invention [0003] The present invention now provides new pyrazolylcarboxanilide compounds represented by formula (I) [0004] [0005] in [0006] R represents difluoromethyl or trifluoromethyl, [0007] R 1 and R 2 Represents halogen, cyano, nitro, C independently of each other 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 1 -C 4 -Alkoxy, C 1 -C 4 -Alkylthio, C 1 -C 4 -Alkylsulfonyl,...

Claims

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Application Information

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IPC IPC(8): A01N43/56C07B61/00C07D231/14
CPCC07D231/14A01N43/48
Inventor R·敦克尔H·里克H·-L·埃尔贝U·瓦亨多夫-纽曼K·-H·库克
Owner BAYER CROPSCIENCE AG
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