Picolinamide derivatives useful as agricultural fungicides

A compound of formula I, or an agronomically acceptable salt or N-oxide thereof:

• Y1 is O;
• R1, R5a and R15 are each independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halogen, nitro, OR11, SR12, OS(O)2R12, S(O)2R12, C(O)OR12, C(O)NR12R12, C(O)R12, S(O)2NR12R12, S(O)(NR12)R12, S(O)R12, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR12R13,
• R2 and R3 are each independently selected from H, C1-C4-alkyl, C3-C6-cycloalkyl, C(O)R14, C(O)OR14, CH2OC(O)R14 and CH2OC(O)OR14;
• R4 is independently at each occurrence selected from:
• H, C3-C6-cycloalkyl, C1-C6-alkyl and benzyl;
• or R3 and R4 together form a group independently selected from C1-C2-alkylene, —C(O)— and —C(S)—;
• R5 is quinoline;
• wherein R5 is substituted with from 1 to 5 R5a groups and/or a single Z1—Z2—R6 group;
• Z1 is independently absent or is CR8R9;
• Z2 is independently absent or is selected from C(O)O, OC(O), O, S, S(O), S(O)2, C(O)NR7, NR7C(O), S(O)2NR7, NR7S(O)2, S(O)NR7, NR7S(O), CR8R9, C(O), C(S), C═NOR10, and NR7;
• R6 is independently at each occurrence selected from C3-C8-alkyl and C0-C3-alkylene-R6a, wherein R6a is independently at each occurrence selected from phenyl, 5- or 6-membered heteroaryl, 5-, 6-, 7- or 8-membered heterocycloalkyl and C5-C8-cycloalkyl;
• said heterocycloalkyl or cycloalkyl group being monocyclic or bicyclic;
• said heteroaryl or phenyl group being optionally substituted with from 1 to 5 R15 groups or said heterocycloalkyl or cycloalkyl group being optionally substituted with from 1 to 4 R16 groups;
• R16 is independently at each occurrence selected from:
• ═O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl;
• halogen, nitro, OR11, SR12, OS(O)2R12, S(O)2R12, S(O)2NR12R12, S(O)(NR12)R12, S(O)R12, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR12R13;
• R7 and R12 are each independently at each occurrence selected from:
• H, C3-C6-cycloalkyl, C1-C6-alkyl and benzyl;
• or where two R12 groups are attached to the same nitrogen atom, said R12 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
• R8 is independently at each occurrence selected from:
• H, C3-C6-cycloalkyl, C1-C6-alkyl, phenyl and 5- or 6-membered heteroaryl;
• R9 is independently at each occurrence selected from:
• H, halo and OR10;
• or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6-cycloalkyl ring or a 3-, 4-, 5- or 6-membered heterocycloalkyl ring;
• R10 is each independently at each occurrence selected from:
• H, C3-C6-cycloalkyl, C1-C6-alkyl and C1-C3-alkylene-R10a, wherein R10a is independently at each occurrence selected from phenyl and 5- or 6-membered heteroaryl;
• R11 is independently at each occurrence selected from:
• H, C1-C0-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl and C1-C6-haloalkyl;
• R13 is independently at each occurrence selected from;
• H, C1-C6-alkyl, C(O)—C1-C6-alkyl and S(O)2-C1-C6-alkyl;
• or where an R12 group and an R13 group are attached to the same nitrogen atom, said R12 and R13 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
• R14 is independently at each occurrence:
• C1-C6-alkyl, phenyl, benzyl and C3-C6-cycloalkyl;
• n is independently an integer selected from 0, 1 and 2;
• and
• wherein any aforementioned alkyl, alkylene, alkenyl, cycloalkyl, heterocycloalkyl (including where two R12 groups or an R12 group and an R13 group together with a nitrogen to which they are attached form a heterocycloalkyl ring), alkynyl, C(O)-alkyl, S(O)2-alkyl and benzyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of:
• ═O;
• ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, ORa and SRa;
• wherein Ra is independently selected from H and C1-C4-alkyl;
• and Rb is independently selected from H, C1-C4-alkyl, C(O)—C1-C4-alkyl and S(O)2-C1-C4-alkyl.