Fungicidal oxadiazoles

A compound selected from Formula 1, tautomers, N-oxides, and salts thereof,

• wherein
• A is S, S(═O) or S(═NR3);
• R3 is H, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C1-C3 alkylsulfonyl or C1-C3 haloalkylsulfonyl;
• R1 is R1aZ1a— or R1bZ1b—;
• R2 is R2aZ2a— or R2bZ2b—;
• or
• R1 and R2 are taken together with the sulfur atom to which they are attached to form a 4- to 6-membered fully saturated heterocyclic ring containing ring members, in addition to the sulfur atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O and up to 2 N atoms, each ring optionally substituted with up to 3 substituents independently selected from halogen and C1-C3 alkyl on carbon atom ring members and C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylsulfonyl and C1-C4 haloalkylsulfonyl on nitrogen atom ring members;
• or
• R1 and R2 are taken together with the sulfur atom to which they are attached to form a dibenzothiophene tricyclic ring system;
• R1a and R2a are each independently C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C3-C8 haloalkoxyalkoxyalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 haloalkylsulfonylalkyl, C2-C6 alkylaminoalkyl, C3-C8 dialkylaminoalkyl, C3-C8 alkylcarbonylalkyl, C3-C8 haloalkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C3-C8 haloalkoxycarbonylalkyl, C3-C8 alkylcarbonyloxyalkyl, C3-C8 haloalkylcarbonyloxyalkyl, C3-C8 alkylaminocarbonylalkyl or C4-C8 dialkylaminocarbonylalkyl;
• Z1a and Z2a are each independently a direct bond or NR4a;
• R1b and R2b are each independently phenyl optionally substituted with up to 5 substituents independently selected from R5a;
• or a 5- to 6-membered heteroaromatic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 5 substituents independently selected from R5a;
• or a 3- to 7-membered nonaromatic ring or an 8- to 11-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and optionally up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O)2, each ring or ring system optionally substituted with up to 5 substituents independently selected from R5a;
• Z1b and Z2b are each independently a direct bond, NR4b or (CR6aR6b)m;
• m is 1 or 2;
• R4a and R4b are each independently H, C1-C3 alkyl or C1-C3 haloalkyl;
• or
• R1a and R4a are taken together with the nitrogen atom to which they are attached to form a 4- to 6-membered fully saturated heterocyclic ring containing ring members, in addition to the nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O and up to 2 N atoms, each ring optionally substituted with up to 4 substituents independently selected from halogen and C1-C3 alkyl on carbon atom ring members and C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylsulfonyl and C1-C4 haloalkylsulfonyl on nitrogen atom ring members;
• each R6a and R6b is independently H, halogen, C1-C3 alkyl or C1-C3 haloalkyl;
• L is (CR7aR7b)n;
• each R7a and R7b is independently H, cyano, hydroxy, nitro, halogen, C1-C3 alkyl or C1-C3 haloalkyl;
• n is 0, 1, 2 or 3;
• J is selected from the group consisting of:
• wherein the bond extending to the left is attached to L, and the bond extending to the right is attached to the 5-(trifluoromethyl)-1,2,4-oxadiazole ring;
• each R8 is independently F, Cl, methyl or methoxy;
• q is 0, 1 or 2;
• each R5a is independently cyano, halogen, hydroxy, nitro, NR9aR9b, C(═O)NR9aR9b, C(═S)NR9aR9b, C(R10)═NR11 or —U—V-Q;
• or C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonyloxy, C2-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C5 alkylcarbonyloxy, C2-C5 alkoxycarbonyloxy, C2-C5 alkylaminocarbonyloxy, C2-C5 alkylcarbonylamino, C2-C5 alkoxycarbonylamino, C2-C5 alkylaminocarbonylamino, C2-C5 dialkoxyphosphinyl or C3-C9 trialkylsilyl, each optionally substituted with up to 3 substituents independently selected from R12;
• each R9a is independently H, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C2-C4 alkoxyalkyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C4 alkylaminocarbonyl or C3-C5 dialkylaminocarbonyl;
• each R9b is independently H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 hydroxyalkyl, C2-C4 cyanoalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylaminoalkyl, C2-C4 haloalkylaminoalkyl or C3-C5 dialkylaminoalkyl, each optionally substituted with up to 1 substituent selected from cyano, hydroxy, nitro, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C3-C9 trialkylsilyl and C3-C9 halotrialkylsilyl;
• or
• R9a and R9b are taken together with the nitrogen atom to which they are attached to form a 4- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 3 substituents independently selected from halogen and C1-C3 alkyl;
• each R10 is independently H, cyano, halogen, methyl, methoxy or methoxycarbonyl;
• each R11 is independently hydroxy or NR13aR13b;
• or C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C2-C4 alkylcarbonyloxy, C2-C5 alkoxycarbonyloxy, C2-C5 alkylaminocarbonyloxy or C3-C5 dialkylaminocarbonyloxy, each optionally substituted with up to 1 substituent selected from cyano, halogen, hydroxy and C(═O)OH;
• each R12 is independently cyano, halogen, hydroxy, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkoxy, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C1-C4 alkylamino, C2-C4 dialkylamino, C2-C5 alkylaminocarbonyl, C3-C5 dialkylaminocarbonyl, C3-C9 trialkylsily, C3-C9 halotrialkylsilyl, C(R14)═NOR15 or C(R16)═NR17;
• each U is independently a direct bond, C(═O)O, C(═O)N(R18) or C(═S)N(R19);
• each V is independently a direct bond;
• or C1-C6 alkylene, C2-C6 alkenylene, C3-C6 alkynylene, C3-C6 cycloalkylene or C3-C6 cycloalkenylene, each optionally substituted with up to 3 substituents independently selected from halogen, cyano, nitro, hydroxy, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy and C1-C2 haloalkoxy;
• each Q is independently phenyl or phenoxy, each optionally substituted with up to 2 substituents independently selected from R20;
• or
• each Q is independently a 5- to 6-membered heteroaromatic, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 2 substituents independently selected from R20;
• or
• each Q is independently a 3- to 7-membered nonaromatic heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O)2, each ring optionally substituted with up to 2 substituents independently selected from R20;
• each R13a is independently H, C1-C4 alkyl or C2-C4 alkylcarbonyl;
• each R13b is independently H, cyano, C1-C4 alkyl, C2-C5 alkylcarbonyl, C2-C5 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl or C3-C5 dialkylaminocarbonyl;
• or
• R13a and R13b are taken together with the nitrogen atom to which they are attached to form a 5- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 methyl groups;
• each R14 and R16 is independently H, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl or C1-C3 alkoxy;
• each R15 is independently H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C4 alkylcarbonyl or C2-C5 alkoxycarbonyl;
• or
• each R15 is phenyl optionally substituted with up to 2 substituents independently selected halogen and C1-C3 alkyl;
• or a 5- to 6-membered fully saturated heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 substituents independently selected from halogen and C1-C3 alkyl;
• each R17 is independently H, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• each R18 and R19 is independently H, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkoxycarbonyl or C2-C4 haloalkoxycarbonyl;
• and
• each R20 is independently halogen, cyano, hydroxy, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C1-C4 alkoxy, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• provided that:
• (a) at most, only one NR4a and NR4b is present in the compounds of Formula 1;
• and
• (b) when NR4a or NR4b is present in the compounds of Formula 1, then A is S(═O) or S(N═R3).