Imidazole fungicides

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

• wherein
• Q1 is a phenyl, thienyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl ring, each ring optionally substituted with up to 5 substituents independently selected from R4a;
• Q2 is a phenyl, thienyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl ring, each ring optionally substituted with up to 5 substituents independently selected from R4b;
• R1 is H, halogen, cyano, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C1-C3 hydroxyalkyl, C2-C3 cyanoalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C1-C3 haloalkylthio;
• R2 is H, halogen, cyano, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C1-C3 hydroxyalkyl, C2-C3 cyanoalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C1-C3 haloalkylthio;
• R3 is H, hydroxy, —CH(═O), C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C6 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C6 alkoxyalkyl, C2-C6 cyanoalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkyl(thiocarbonyl), C2-C6 alkoxy(thiocarbonyl) or —S(═O)2OM;
• each R4a and R4b is independently halogen, cyano, hydroxy, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C2-C3 cyanoalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C2-C3 alkylcarbonyl, C1-C3 alkylamino, C2-C3 dialkylamino, C2-C3 alkylcarbonylamino, —SC≡N, —C(≡W)NH2 or -T-U—V;
• each T is independently O, S(═O)n, NR5 or a direct bond;
• each U 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 independently selected from 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 V is independently cyano, N(R6a)(R6b), OR7 or S(═O)—R7;
• each R5 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 R6a and R6b 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 R6a and R6b are taken together with the nitrogen atom to which they are attached to form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R8;
• each R7 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);
• each R8 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
• each W is independently O or S;
• M is K, Na or Li;
• each n is independently 0, 1 or 2;
• provided that:
• (a) when R1 is H, R2 is other than H;
• (b) the compound is other than N-(2,5-dichlorophenyl)-4-methyl-5-phenyl-1H-imidazol-1-amine;
• and
• (c) when Q1 and Q2 are each an optionally substituted phenyl ring, then Q1 is substituted with at least one R4a at an otho position, or Q2 is substituted with at least one R4b at an otho position.