5-phenylpyrimidines, their preparation, intermediates for their preparation, and their use for controlling harmful fungi

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Quick Facts

Patent No.: US 7,709,637
App. No.: 11/548,864
Granted: May 4, 2010
Kind: B2

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Abstract

5-Phenylpyrimidines of the formula I, in which the substituents have the following meanings: R 1 is a five- to ten-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle comprising one to four hetero atoms selected from the group consisting of O, N or S, which heterocycle can be substituted as defined in the description, R 2 is hydrogen, halogen, cyano, alkyl, haloalkyl or alkoxy; R 3 , R 4 are hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, cycloalkenyl, alkynyl, haloalkynyl or cycloalkynyl, R 3 and R 4 together with the nitrogen atom to which they are bonded may also form a five- or six-membered ring which can be interrupted by a hetero atom and have attached to it one or more substituents; R 5 , R 6 are hydrogen, halogen, alkyl, haloalkyl or alkoxy; R 7 , R 8 are hydrogen, halogen, alkyl or haloalkyl; R 9 is hydrogen, halogen, alkyl, alkoxy, cycloalkoxy, haloalkoxy or alkoxycarbonyl, Processes and intermediates for the preparation of these compounds, and their use for controlling harmful fungi.

Claims (34)

1. An intermediate of formula VI, VIa, VIII or IX

wherein

R is C 1 -C 6 -alkyl;

R 3 , R 4 are, independently of one another, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, or C 2 -C 6 -haloalkynyl, or

R 3 and R 4 are, together with the nitrogen atom to which they are bonded, a five- or six-membered ring which can be interrupted by O and which can have attached to it a C 1 -C 6 -alkyl substituent;

is a five to ten-membered saturated, partially unsaturated or aromatic heterocycle consisting of carbon atoms and from one to four heteroatoms selected from the group consisting of O, N and S, which is bonded via carbon, and which is optionally substituted by one to three identical or different groups R a ;

R a is halogen, hydroxyl, cyano, oxo, nitro, amino, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, carboxyl, C 1 -C 7 -alkoxycarbonyl, carbamoyl, C 1 -C 7 -alkylaminocarbonyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C 1 -C 7 -alkylcarbonylamino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C 1 -C 6 -alkylaminosulfonyl or di(C 1 -C 6 -alkyl)aminosulfonyl; and

the combination of the substituents R 5 to R 9 has the following meanings:

in formula VI: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy and pentafluoro, in formula VIa: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,6-fluoro; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy; and pentafluoro, and

in formulae VIII and IX: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,6-fluoro; 2,4,6-trifluoro; 2,6-difluoro, 4-methoxy; and pentafluoro.

2. An intermediate defined in claim 1 , wherein

is pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3-triazine, 1,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, thiazole, isothiazole, pyridazine, pyrimidine or pyrazine, which is bonded to the pyrimidine ring via carbon, and which is optionally substituted by one to three identical or different groups R 1 ,

R a is halogen, hydroxyl, cyano, nitro, amino, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, carboxyl, C 1 -C 7 -alkoxycarbonyl, carbamoyl, C 1 -C 7 -alkylaminocarbonyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C 1 -C 7 -alkylcarbonylamino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C 1 -C 6 -alkylaminosulfonyl or di(C 1 -C 6 -alkyl)aminosulfonyl.

3. An intermediate defined in claim 1 , wherein

is pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3-triazine, 1,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, thiazole, or isothiazole, which is bonded to the pyrimidine ring via carbon, and which is optionally substituted by one to three identical or different groups R a ,

4. An intermediate defined in claim 1 , wherein

is pyrazole, pyrrole, imidazole, 1,2,3-triazole, or 1,2,4-triazole which is bonded to the pyrimidine ring via carbon, and which is optionally substituted by one to three identical or different groups R a ,

5. An intermediate defined in claim 1 , wherein

R 3 , R 4 are, independently of one another, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkenyl, or

R 3 and R 4 are, together with the nitrogen atom to which they are bonded, a five or six-membered ring which can be interrupted by an oxygen atom and which can have attached to it a C 1 -C 6 -alkyl substituent.

6. An intermediate of formula VIa defined in claim 1 , wherein the combination of the substituents R 5 to R 9 has the following meanings: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,6-fluoro; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy and pentafluoro.

7. An intermediate of formula VIII or IX defined in claim 1 , wherein the combination of the substituents R 5 to R 9 has the following meanings: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,6-fluoro; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy; and pentafluoro.

8. An intermediate of formula VIa, VIII or IX defined in claim 1 , wherein the combination of the substituents R 5 to R 9 has the following meanings: 2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,6-fluoro; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy; and pentafluoro.

9. An intermediate of formula VIa

wherein

R is C 1 -C 6 -alkyl;

R 3 , R 4 are, independently of one another, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or C 3 -C 6 -cycloalkynyl, or

R 3 and R 4 are, together with the nitrogen atom to which they are bonded, a five or six-membered ring which can be interrupted by a hetero atom selected from the group consisting of O, N and S and/or which can have attached to it one or more substituents selected from the group consisting of halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and oxy-C 1 -C 3 -alkylenoxy or in which two adjacent C atoms or one N atom and one adjacent C atom can be linked by a C 1 -C 4 -alkylene chain;

the combination of the substituents R 5 to R 9 has the following meanings:

2-chloro,6-fluoro; 2,6-difluoro; 2,6-dichloro; 2-methyl,4-fluoro; 2-methyl,6-fluoro; 2-fluoro,4-methyl; 2,4,6-trifluoro; 2,6-difluoro,4-methoxy; 2,4-dimethyl and pentafluoro.