Pyridine compounds for combatting dihydroorotate-dehydrogenase inhibitor-resistant phytopathogenic fungi

A method for combatting dihydroorotate-dehydrogenase (DHODH) inhibitor-resistant phytopathogenic fungi comprising:

• treating the phytopathogenic fungi or materials, plants, soil or seeds that are at risk of being diseased from the phytopathogenic fungi with an effective amount of at least one compound of formula I
• where
• R1 is hydrogen, halogen, CN, C1-C4-alkyl or C1-C4-haloalkyl;
• R2 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy;
• R3 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy;
• R4 is hydrogen, halogen, CN, C1-C4-alkyl or C1-C4-haloalkyl;
• R5 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the 8 last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1, 2 or 3 substituents R5a;
• where each R5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
• R6 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the 8 last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1, 2 or 3 substituents R6a;
• where
• each R6a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
• or
• R5 and R6 form together an oxo group (═O);
• or
• R5 and R6, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members;
• where the carbocyclic or heterocyclic ring is unsubstituted or carries 1, 2 or 3 substituents R56;
• where
• each R56 is independently halogen, C1-C6-alkyl or C1-C6-haloalkyl;
• R7 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the 8 last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1, 2 or 3 substituents R7a;
• where
• each R7a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
• R8 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the 8 last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1, 2 or 3 substituents R8a;
• where each R8a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
• or
• R7 and R8, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members;
• each X is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• Y is O if m is 1;
• and is O or NR9 if m is 0;
• where
• R9 is hydrogen, CN, CH2CN, CH(CH3)CN, CH(═O), —C(═O)C1-C6-alkyl, —C(═O)C2-C6-alkenyl, —C(═O)C2-C6-alkynyl, —C(═O)C3-C6-cycloalkyl, —C(═O)—N(H) C1-C4-alkyl, —C(═O)—N(C1-C4-alkyl)2, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,
• —S(═O)2-R9a, five- or six-membered heteroaryl, aryl or benzyl;
• wherein heteroaryl contains 1,2 or 3 heteroatoms selected from N, O and S as ring members;
• wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1, 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• wherein
• R9a is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the phenyl ring in the two last-mentioned radicals is unsubstituted or carries 1, 2 or 3 substituents each independently selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl;
• m is 0 or 1;
• and
• n is 0, 1, 2 or 3;
• or an N-oxide, a tautomer, a stereoisomer or an agriculturally acceptable salt thereof.