Patent CA-2107084-A1 (CA)
Title: Fungicides
Inventor: DE FRAINE PAUL J
IPC: A01N43/06
Filed: 1992-04-14
Abstract: Compounds having formula (I), wherein A is hydrogen, halogen, hydroxy, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy or cyano; and one of R1 and R2 is methyl and the other is pyridyl or pyrimidinyl substituted by one or more substituents independently selected from halogen, hydroxy, C1-6 alkyl (itself optionally substituted by C1-6 alkoxy), C1-6 haloalkyl, C1-6 alkoxy (optionally substituted by halogen, R3R4N, cyano, R3C(O), R3OC(O), R3R4NC(O), R3SC(O), H2N.NHC(O), R3S(O)m wherein m is 0, 1 or 2, C3-6 cycloalkyl [itself optionally substituted by C1-4 alkyl] or a 5- or 6-membered heterocyclic ring containing one or two oxygen atoms, optionally being in the form of a lactone, the heterocyclic ring being optionally fused to a benzene ring and optionally substituted by C1-4 alkyl), R3S(O)n wherein n is 0, 1 or 2, C2-6 alkenyl, C2-6 alkynyl, C2-6 alkenyloxy, C2-6 alkynyloxy, nitro, cyano, CO2R3, NR3R4, NR3R4C(O), NR3R4C(S), R3R4C:NO, C3-6 cycloalkyl, C3-6 cycloalkyloxy (itself optionally substituted by C1-4 alkyl), C1-6 alkoxy(C1-6)alkoxy, an aromatic 5-membered ring containing 1, 2 or 3 nitrogen atoms (itself optionally substituted by C1-4 alkyl), C1-6 alkoxy(C1-6)haloalkoxy, phenoxy(C1-4)alkoxy, phenyl(C1-4)alkoxy(C1-6)alkoxy, C1-4alkoxy(C1-6)alkoxy(C1-6)alkoxy, di(C1-4alkoxy)-(C1-6)alkoxy, C2-6 alkenyloxy(C1-6)alkoxy, C2-6 alkenyloxy(C1-6)haloalkoxy, a 5- or 6-membered heterocyclic ring containing one or two heteromoieties independently selected form N, S, S(O), S(O)2 or O and optionally being fused to a benzene ring, the heterocyclic ring being optionally substituted by C1-4 alkyl and when it contains an oxygen atom it may be in the form of a lactone, the heterocyclic ring is linked directly to the pyridine or pyrimidine ring or is linked through an O, OCH2 or CH2O moiety, phenyl, phenoxy or phenyl(C1-4)alkoxy; wherein any of the foregoing phenyl moieties is optionally substituted by halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, nitro or cyano, or the other of R1 and R2 is a pyridine or pyrimidine ring optionally substituted with any of the moieties already listed as substitutents for pyridine and pyrimidine rings above and fused to an aromatic 5-membered ring containing one or two heteroatoms independently selected from nitrogen, oxygen and sulphur; and R3 and R4 are independently hydrogen or C1-6 alkyl (itself optionally substituted by halogen or cyano); provided that when A is hydrogen and one of R1 and R2 is methyl then the other is not: pyrid-2-yl monosubstituted with chloro, cyano, fluoro, bromo, methyl or 5-ethyl, or substituted with 3-5-difluoro or 3,4,5,6-tetrafluoro; pyrid-3-yl substituted with 6-methyl, 4-cyano, 5-cyano, 6-cyano or 2,6-dichloro; pyrid-4-yl monosubstituted with cyano;  pyrimidin-2-yl substituted with 4-methyl, 4,6-dimethyl or 4,6-dimethoxy; pyrimidin-4-yl substituted with 2-chloro, 2-methoxy, 2-methyl, 2-cyano, 6-methyl, 6-chloro, 6-methoxy, 6-phenyl or 2,6-dimethyl; or pyrimidin-5-yl substituted with 2-methyl, 4-methyl or 2,4-dimethyl. The compounds of formula (I) are useful as fungicides.