Pyridazine (thio)amides as fungicidal compounds

13:

• A process for preparing a compound of formula (I) as recited in claim 1,
• wherein R1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, —C(═O)Ra1, —C(═O)(ORa1), —S(═O)Ra1, —S(═O)2Ra1, —C(═O)N(Ra2)2 or S(═O)2N(Ra2)2, and T is O,
• comprising a step of reacting a compound of formula (1)
• wherein U1 is hydroxyl, halogen or C1-C6-alkoxy,
• with an amine of formula (2)
• wherein
• R1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, —C(═O)Ra1, —C(═O)(ORa1), —S(═O)Ra1, —S(═O)2Ra1, —C(═O)N(Ra2)2 or S(═O)2N(Ra2)2.

14:

• A process for preparing a compound of formula (I) as recited in claim 1,
• wherein R1 is hydrogen, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, T is O, R8 is hydrogen or C1-C6-alkyl, R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2, comprising a step of reacting a compound of formula (3)
• wherein G is halogen, R1 is hydrogen, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, R8 is hydrogen or C1-C6-alkyl, R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2, with a compound of formula (4)
• in the presence of a base.

15:

• A compound of formula (1):
• wherein U1 is hydroxyl, halogen or C1-C6-alkoxy;
• R7 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Re)2, —C(═NRf)Rf, —NRgC(═O)Rg, —C(═O)(ORg), —C(═O)N(Rg)2, —S(═O)2N(Rg)2 and —S(═O)(═NRg)Rg,
• wherein each Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
• wherein each Rf is independently selected from the group consisting of hydroxyl, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino and di(C1-C6-alkyl)amino,
• wherein each Rg is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,
• wherein aliphatic R7, Re, Rf and Rg substituents may be substituted with one or more R7Sa substituents that may be the same or different,
• wherein cyclic or cyclic moiety of R7, cyclic Re and cyclic Rg substituents may be substituted with one or more R7Sc substituents that may be the same or different,
• R7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, aromatic C6-C14-carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle, R7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle, or two R7Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl:
• R8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, non-aromatic 3- to 14-membered heterocyclyloxy, aromatic 5- to 14-membered heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Rh)2, —SRi, —S(═O)Ri and —S(═O)2Ri,
• wherein each Rh is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
• wherein each Ri is selected from the group consisting of C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
• wherein aliphatic Rg, Rh and Ri substituents may be substituted with one or more R8Sa substituents that may be the same or different,
• wherein cyclic or cyclic moiety of Rg, cyclic Rh and cyclic Ri substituents may be substituted with one or more R8Sc substituents that may be the same or different,
• R8Sa is selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, non-aromatic 3- to 7-membered monocyclic heterocycle and —N(Ra′)2 with Ra′ being independently selected from the group consisting of hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C1-C6-alkylcarbonyl, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle R8Sa may be substituted with one or more C1-C6-alkyl substituents that may be the same or different,
• R8Sc is selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle that may be substituted with one or more C1-C6-alkyl substituents that may be the same or different, or two R8Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle may be substituted with one or more C1-C6-alkyl substituents that may be the same or different:
• Q is selected from the group consisting of aromatic C6-C14-carbocycle, non-aromatic C3-C12-carbocycle, non-aromatic 3- to 14-membered heterocycle and aromatic 5- to 14-membered heterocycle, wherein any of said carbocycle or heterocycle groups may be substituted with one or more QS substituents that may be the same or different,
• QS is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, non-aromatic 3- to 7-membered monocyclic heterocycle, aromatic 5- to 14-membered heterocycle, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —O—C(═O)Rj, —NRC(═O)Rj, —C(═O)N(Rj)2, —C(═S)Rj, —C(═S)N(Rj)2, —C(═NRj)Rj, —C(═NORj)Rj and —N(Rk)2
• wherein each Ri is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy,
• wherein each Rj is independently selected from the group consisting of hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl and C3-C8-cycloalkyl,
• wherein aliphatic QS, Rj and Rk substituents may be substituted with one or more substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle,
• wherein cyclic or cyclic moiety of QS and cyclic Rk substituents may be substituted with one or more RQs substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and non-aromatic 3- to 7-membered monocyclic heterocycle, wherein cyclic RQs substituents may be substituted with two substituents forming, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl;
• and
• R7 and R8 are not simultaneously hydrogen, C1-C6-alkyl, or aromatic C6-C14-carbocycle,
• provided that the compound is not:
• methyl 6-chloro-3-(2,4-difluorophenoxy)pyridazine-4-carboxylate,
• 6-chloro-3-[(8-formyl-4-methyl-2-oxo-2H-chromen-7-yl)oxy]pyridazine-4-carboxylic acid,
• 6-chloro-3-[(3-formyl-7-methylquinolin-2-yl)oxy]pyridazine-4-carboxylic acid,
• 6-chloro-3-{[4-formyl-5-(hydroxymethyl)-2-methylpyridin-3-yl]oxy}pyridazine-4-carboxylic acid,
• 6-chloro-3-[(1-formyl-2-naphthyl)oxy]pyridazine-4-carboxylic acid,
• 6-chloro-3-(2-formyl-5-methoxyphenoxy)pyridazine-4-carboxylic acid, or
• ethyl 3-phenoxy-6-phenylpyridazine-4-carboxylate.

16:

• A compound of formula (3):
• wherein
• G is halogen;
• n=1 and m=1;
• R1 is hydrogen;
• R2, R3, are hydrogen;
• R4 and R5 are hydrogen or fluorine;
• R6 is selected from the group consisting of non-aromatic polycyclic C7-C12-carbocycle, aromatic C6-C14-carbocycle, and non-aromatic 6- to 14-membered polycyclic heterocycle;
• R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2,
• wherein each Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
• wherein aliphatic R7 and Re substituents may be substituted with one or more R7Sa substituents that may be the same or different,
• wherein cyclic or cyclic moiety of R7 and cyclic Re substituents may be substituted with one or more R7Sc substituents that may be the same or different,
• R7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, aromatic C6-C14-carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
• R7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle, or two R7Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl;
• and
• R8 is hydrogen or C1-C6-alkyl;
• provided that the compound of formula (3) is not:
• 3,6-dichloro-N-[2-(3,5-difluorophenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(3-methylphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(3-chlorophenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(4-fluoro-2-methylphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(2-methylphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(4-hydroxyphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(3-fluorophenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(2-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(4-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(4-fluorophenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(2,4-dichlorophenyl)ethyl]pyridazine-4-carboxamide,
• 3,6-dichloro-N-[2-(2-fluorophenyl)ethyl]pyridazine-4-carboxamide, or
• 3,6-dichloro-N-(2-phenylethyl)pyridazine-4-carboxamide.