US 7,320,975 B2
2-(2-pyridyl)-5-phenyl-6-aminopyrimidine, method and intermediate products for the production and use thereof for combating noxious fungi
Frank Schieweck, Hessheim (Germany); Jordi Tormo i Blasco, Limburgerhof (Germany); Thomas Grote, Wachenheim (Germany); Andreas Gypser, Mannheim (Germany); Bernd Müller, Frankenthal (Germany); Joachim Rheinheimer, Ludwigshafen (Germany); Ingo Rose, Mannheim (Germany); Peter Schäfer, Ottersheim (Germany); Wassilios Grammenos, Ludwigshafen (Germany); Markus Gewehr, Kastellaun (Germany); Anja Schwögler, Mannheim (Germany); Carsten Blettner, Ludwigshafen (Germany); Eberhard Ammermann, Heppenheim (Germany); Siegfried Strathmann, Limburgerhof (Germany); Gisela Lorenz, Hambach (Germany); and Reinhard Stierl, Mutterstadt (Germany)
Assigned to BASF Aktiengesellschaft, Ludwigshafen (Germany)
Appl. No. 10/505,146
PCT Filed Feb. 06, 2003, PCT No. PCT/EP03/01162
§ 371(c)(1), (2), (4) Date Aug. 20, 2004,
PCT Pub. No. WO03/070721, PCT Pub. Date Aug. 28, 2003.
Claims priority of application No. 102 07 428 (DE), filed on Feb. 21, 2002; and application No. 102 10 136 (DE), filed on Mar. 08, 2002.
Prior Publication US 2005/0107401 A1, May 19, 2005
Int. Cl. C07D 401/04 (2006.01); A01N 43/54 (2006.01)
U.S. Cl. 514—235.8  [514/256; 544/122; 544/319; 544/328; 544/333] 22 Claims
 
1. A 2-(2-pyridyl)-5-phenyl-6-aminopyrimidine of the formula I,

OG Complex Work Unit Drawing
wherein:
R1 is halogen, hydroxyl, cyano, oxo, nitro, amino, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, carboxyl, C1-C7-alkoxycarbonyl, carbamoyl, C1-C7-alkylaminocarbonyl, C1-C6-alkyl-C1-C6-alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C1-C7-alkylcarbonylamino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C1-C6-alkylaminosulfonyl or di(C1-C6-alkyl)aminosulfonyl;
m is 0, 1, 2, 3 or 4;
R2 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C6-alkenyloxy;
R3, R4 independently of one another, are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl or C3-C6-cycloalkynyl, or
R3 and R4 can also, together with the nitrogen atom to which they are bonded, form a five- or six-membered ring which may be interrupted by an atom from the group consisting of O, N and S and/or may carry one or more substituents from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl or oxy-C1-C3-alkylenoxy or in which two adjacent carbon atoms or one N— and one neighboring carbon atom can be connected via a C1-C4-alkylene chain;
R5 is halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R6 is hydrogen or one of the groups mentioned under R5;
R7, R8 independently of one another, are hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R9 is hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl or C1-C6-alkylaminocarbonyl.