Substituted fused bicyclic pyridine carboxamide compounds for combating phytopathogenic fungi

A compound of formula (I);

• wherein,
• “═” indicates presence or absence of double bond;
• X is O or S;
• Z1 is C(R4)1-2, CHR4—*CHR4, O—*CHR4, O, S, or N(R10)0-1;
• wherein the carbon atom marked with “*” indicates the point of attachment to the carbon atom marked with “#”;
• Z2 is C(R4)1-2 or NR10;
• provided that
• a) when Z1 is S and Z2 is CR4 then R5 and R6 will not form a ring;
• b) when Z1 is NH, Z2 is NH and R3 is oxo then R5 and R6 will not form a ring;
• c) when Z1 is N, and Z2 is N(CH3) then R5 and R6 will not form a ring;
• R1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C10-cycloalkyl and phenoxy;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C10-cycloalkyl and phenoxy may optionally be substituted with one or more groups of R1a;
• R1a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy;
• R2 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C10-cycloalkyl and phenoxy;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C10-cycloalkyl and phenoxy may optionally be substituted with one or more groups of R2a;
• R2a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy;
• R3 is selected from the group consisting of hydrogen, halogen, oxo, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C10-cycloalkyl;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C10-cycloalkyl may optionally be substituted with one or more groups of R3a;
• R3a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy;
• R4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C10-cycloalkyl;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C10-cycloalkyl may optionally be substituted with one or more groups of R4a;
• R4a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy;
• R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C3-C10-cycloalkyl, C3-C10-cycloalkyl-C1-C6-alkyl and C6-C10-aryl;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C3-C10-cycloalkyl, C3-C10-cycloalkyl-C1-C6-alkyl and C6-C10-aryl may optionally be substituted with one or more groups of R5a;
• or
• R5 and R6 together with the atoms to which they are attached may form a 3 to 6 membered non-aromatic carbocyclic ring, or non-aromatic heterocyclic ring;
• wherein one or more heteroatoms of said ring are selected from N, O or S(═O)0-2 and one or more C atom/s of the ring may optionally be replaced by C(═O), C(═S);
• the ring may optionally be substituted with one or more identical or different groups of R5a;
• R5a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C10-cycloalkyl and C1-C6-alkoxy-C1-C6-alkyl;
• R7 and R8 are each independently selected from the group consisting of hydrogen, cyano, halogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl and C3-C10-cycloalkyl;
• wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl and C3-C10-cycloalkyl may optionally be substituted with one or more groups of R7a;
• or
• R7 and R8 together with the atoms to which they are attached may form a 3 to 6 membered non-aromatic or aromatic carbocyclic ring, or non-aromatic or aromatic heterocyclic ring;
• wherein one or more heteroatoms of said ring are selected from N, O or S(a)0-2 and one or more C atom/s of the ring may optionally be replaced by C(═O) or C(═S);
• the ring may optionally be substituted with one or more identical or different groups of R7a;
• provided that when R7 and R8 forms an aromatic ring then R9 is absent;
• R7a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C10-cycloalkyl and C1-C6-alkoxy-C1-C6-alkyl;
• R9 is selected from the group consisting of hydrogen, halogen, C3-C10-cycloalkyl, C3-C10-cycloalkyloxy, C3-C10-cycloalkenyl, C3-C10-cycloalkenyloxy, C6-C10-aryl, C7-C14-aralkyl, C6-C10-aryloxy, benzyloxy, —O—C(O)—C6-C10-aryl, O—C(O)—C2-C10-heterocyclyl, C2-C10-heterocyclyl and C2-C10-heterocycloxy;
• wherein the heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S;
• and wherein in each case one or two CH2 groups of the carbocycle or heterocycle may be replaced by a group independently selected from C(═O) and C(═S);
• wherein C3-C10-cycloalkyl, C3-C10-cycloalkyloxy, C3-C10-cycloalkenyl, C3-C10-cycloalkenyloxy, C6-C10-aryl, C7-C14-aralkyl, C6-C10-aryloxy, benzyloxy, —O—C(O)—C6-C10-aryl, O—C(O)—C2-C10-heterocyclyl, C2-C10-heterocyclyl and C2-C10-heterocycloxy may optionally be substituted with one or more groups of R9a;
• or
• R5 and R9 together with the atoms to which they are attached may form a 3 to 12 membered non-aromatic carbocyclic ring, or non-aromatic heterocyclic ring;
• wherein one or more heteroatoms of said ring are selected from N, O or S(═O)0-2 and one or more C atom/s of the ring may optionally be replaced by C(═O), C(═S);
• the ring may optionally be substituted with one or more identical or different groups of R9a;
• R9a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C10-cycloalkyl, C(R″)═N—OR′, C3-C10-cycloalkyloxy, C3-C10-cycloalkenyl, C3-C10-cycloalkenyloxy, C6-C10-aryl, C7-C14-aralkyl, C6-C10-aryloxy, C2-C10-heterocyclyl and C2-C10-heterocycloxy;
• R′ is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each group of R′ may optionally be substituted with groups selected from halogen, cyano, C1-C6-alkoxy, C3-C10-cycloalkyl, C3-C10-cycloalkyloxy, C6-C10-aryl, C7-C14-aralkyl and C6-C10-aryloxy;
• R″ is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C10-cycloalkyl and C3-C10-cycloalkenyl;
• R10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C6-alkyl;
• R11 is selected from the group consisting of hydrogen, C1-C6-alkyl and C1-C6-alkoxy;
• each group of R1 to R11, R1a to R5a, R7a or R9a may optionally be substituted with one or more groups selected from cyano, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C10-cycloalkyl, C3-C10-cycloalkenyl and C6-C10-aryl;
• and N-oxides, metal complexes, stereoisomers, polymorphs, or the agriculturally acceptable salts thereof,
• with the proviso that, following compounds are excluded from the definition of compounds of formula (I),
• 2-methyl-N-(2,4,4-trimethylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide,
• N-(tert-butyl)-2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide
• N-(tert-butyl)-2-methyl-5,6,7,8-tetrahydroquinoline-3-carboxamide,
• 2-methyl-N-(2,4,4-trimethylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide,
• N-(1-(2-chlorophenoxy)-2-cyanopropan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide,
• N-(2-cyano-1-(5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide,
• N-(2-(1,2,4-oxadiazol-3-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-cyclohexylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• 3-methyl-N-(1,1,1-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-cyclopropyl-1,1,1-trifluoropropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• 3-methyl-N-(4,4,4-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(4-(azepan-1-yl)-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-cyclohexyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-cyclopropyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(1-hydroxy-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(tert-butyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-methyl-4-(4-methylpiperazin-1-yl)butan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-(3,5-dimethylisoxazol-4-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(1-(3-methoxyphenyl)-2-methylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide,
• N-(2-(tetrahydro-2H-pyran-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide,
• N-(2-methyl-1-morpholinopropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide and
• N-(2-(1-methyl-1H-1,2,3-triazol-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide.