5-Phenylpyrimidines, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi

1. A 5-phenylpyrimidine of the formula I,

in which the substituents have the following meanings:

R 1 is pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, 1,2,3-triazine, l,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, furan, thiophene, thiazole, iso-thiazole, pyridazine, pyrimidine or pyrazine, it being possible for the heterocycle to be bonded to the pyrimidine ring via C or N, it being possible for R 1 to be substiuted 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 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 -alkylamincarbonyl, 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;

R 2 is halogen, cyano, C 1 –C 6 -alkyl, C 1 –C 6 -haloalkyl, C 1 –C 6 -alkoxy, C 1 –C 4 -haloalkoxy or C 3 -C 6 a-lkenyloxy;

R 3 , R 4 independently of one another are 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,

R 3 and R 4 may also, together with the nitrogen atom to which they are bonded, form 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;

R 5 is halogen, C 1 –C 6 -alkyl, C 1 –C 6 -haloalkyl or C 1 –C 6 -alkoxy;

R 6 is hydrogen, halogen, C 1 –C 6 -alkyl, C 3 –C 6 -haloalkyl or C 1–C 6 -alkoxy;

R 7 , R 8 independently of one another are hydrogen, halogen, C 1 –C 6 -alkyl or C 1 –C 6 -haloalkyl;

R 9 is hydrogen, halogen, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 3 –C 6 -cycloalkoxy, C 1 –C 6 -haloalkoxy, C 1 –C 6 -alkoxycarbonyl or C 1 –C 6 -alkylaninocarbonyl.

2. A compound of the formula I as claimed in claim 1 , where the variables have the the following meaning:

R 1 is pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole or tetrazole which are bonded via C or N, or 2-pyrimidine, pyrazine or 3-pyridazine,

in which R 1 can have attached to it up to three substituents R a′

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 -alkylamincarbonyl, 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,

R 2 is halogen, C 1 –C 6 -alkyl or C 1 –C 6 -alkoxy;

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

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

R 5 is halogen or C 1 –C 6 -alkyl;

R 6 is hydrogen, halogen or C 1 –C 6 -alkyl;

R 7 , R 8 independently of one another are hydrogen or halogen;

R 9 is hydrogen, halogen, C 1 –C 6 -alkyl or C 1 –C 6 -alkoxy.

3. A compound of the formula I as claimed in claim 1 , where R 2 is chlorine.

4. A compound of the formula I as claimed in claim 1 , where the combination of the aubstituents 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.

5. A process for the preparation of 5-phenylpyrimidine of the formula I as claimed in claim 1 , in which R 1 is bonded via nitrogen and R 2 is chlorine, which comprises cyclizing thiourea with an alkyl phenylmalonate of the formula II,

in which R is C 1 –C 6 -alkyl to give compounds of the formula III

which are reacted with alkylating agents of the formula IV,

R-X  IV

in which R is C 1 –C 6 -alkyl and X is a nucleophilically exchangable group to give compounds of the formula V

which are converted with chlorinating agents to give the dichloropyrimidines of the formula VI

which are reacted with amino compounds of the formula VII

to give the pyrimidine derivatives of the formula VIII

and oxidizing VIII to give the sulfones of the formula IX

which are converted by reaction with heterocyclic compounds of the formula X

in which the cycle A is a heterocycle (R 1 ) as claimed in claim 1 to give the compound the compounds of the formula I.

6. A process for the preparation of 5-phenylpyrimidines of the formula I as claimed in claim 1 , where {circle around (B)} is a heterocycle R 1 as defined in claim 1 which is bonded via carbon, which process comprises reacting a dichloropyrimidine of the formula VIa,

where {circle around (B)} is the heterocycle R 1 which is bonded via carbon, and the variables have the meanings stated in claim 1 with an amine of the formula VII

where the variables have the meanings stated in claim 1 .

7. Composition suitable for controlling phytopathogenic harmful fungi, comprising a solid or liquid carrier and a compound of the formula I as claimed in claim 1 .

8. A method of controlling phytopathogenic harmful fungi, which comprises treating the fungi or the materials, plants, soil or seeds to be protected against fungal infection with an effective amount of a compound of the formula I as claimed in claim 1 .