Fungicidal pyrazoles

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

• wherein
• Q1 is C3-C6 cycloalkyl or C3-C6 cycloalkenyl, wherein up to 3 carbon atoms are independently selected from C(═O), each optionally substituted with up to 2 substituents independently selected from halogen, cyano, nitro, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy;
• or a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R5;
• or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system 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 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR16)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R5 on carbon atom ring members and selected from cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl and C3 dialkylaminoalkyl on nitrogen atom ring members;
• Q2 is C3-C6 cycloalkyl or C3-C6 cycloalkenyl, wherein up to 3 carbon atoms are independently selected from C(═O), each optionally substituted with up to 2 substituents independently selected from halogen, cyano, nitro, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy;
• or a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R5;
• or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system 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 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR16)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R5 on carbon atom ring members and selected from cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl and C3 dialkylaminoalkyl on nitrogen atom ring members;
• R1 is H, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl or cycloalkyl;
• R1a is H;
• or
• R1a and R1 are taken together with the carbon atom to which they are attached to form a cyclopropyl ring optionally substituted with up to 2 substituents independently selected from halogen and methyl;
• R2 is H, cyano, halogen, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 cyanoalkyl, C1-C3 hydroxyalkyl, C1-C3 alkoxy or C1-C3 alkylthio;
• or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl;
• R3 is H or C1-C6 alkyl;
• R4 is —NR6aR6b or —S(═O)nR7;
• each R5 is independently amino, cyano, halogen, hydroxy, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C6 cycloalkylalkyl, C4-C6 alkylcycloalkyl, C5-C8 cycloalkylalkenyl, C5-C8 cycloalkylalkynyl, C1-C6 nitroalkyl, C1-C6 nitroalkenyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C6 alkylcarbonyloxy, C3-C6 cycloalkoxy, C4-C8 cycloalkylalkoxy, C1-C6 alkylsulfonyloxy, C1-C6 haloalkylsulfonyloxy, C4-C9 trialkylsilylalkoxy, C2-C6 alkylcarbonyl, C1-C6 alkylamino, C1-2—C1-6 dialkylamino, C2-C6 alkylcarbonylamino, C3-C9 trialkylsilyl, C4-C9 trialkylsilylalkyl, C(═S)NR8aR8b, —NH2CH(═O), CR9a═NOR9b, CR9c═NNR8aR8b, NR8aN═CR10aR10b, —ON═CR10aR10b, —CH(═O), SF5, SC≡N or —U—V-T;
• R6a and R6b are each independently H, —CH(═O), C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-C4 alkylsulfinylalkyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl, C3-C5 dialkylaminocarbonyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl;
• R7 is H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkenyl or C2-C3 alkynyl;
• each R8a and R8b is independently H or methyl;
• each R9a is independently H, C1-C3 alkyl or C1-C3 haloalkyl;
• each R9b and R9c is independently H, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C3 haloalkyl, C2-C4 haloalkenyl, C3-C4 cycloalkyl or C3-C4 halocycloalkyl;
• each R10a and R10b is independently H, C1-C3 alkyl or C1-C3 haloalkyl;
• each U is independently O, S(═O)n, NR11 or a direct bond;
• each V is independently C1-C6 alkylene, C2-C6 alkenylene, C3-C6 alkynylene, C3-C6 cycloalkylene or C3-C6 cycloalkenylene, wherein up to 3 carbon atoms are C(═O), each optionally substituted with up to 5 substituents independently selected from halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
• each T is independently cyano, NR12aR12b, OR13 or S(═O)nR14;
• each R11 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl or C4-C8 cycloalkoxy(thiocarbonyl);
• each R12a and R12b is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl or C4-C8 cycloalkoxy(thiocarbonyl);
• or
• a pair of R12a and R12b attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R15;
• each R13 and R14 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl) or C4-C8 cycloalkoxy(thiocarbonyl);
• each R15 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
• each R16 is independently H, cyano, C1-C3 alkyl or C1-C3 haloalkyl;
• each n is independently 0, 1 or 2;
• and
• each u and v are independently 0, 1 or 2 in each instance of S(═O)u(═NR16)v;
• provided that:
• (a) the sum of u and v is 0, 1 or 2;
• (b) when Q1 and Q2 are each an optionally substituted phenyl ring, then at least one of Q1 or Q2 is substituted with at least one R5 substituent;
• and
• (c) at least one of Q1 or Q2 is an aromatic ring.