Fungicidal pyrazoles

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

wherein

Q 1 is a phenyl ring substituted with 1 to 5 substituents independently selected from R 3a ;

Q 2 is a phenyl ring substituted with 1 to 5 substituents independently selected from R 3a ; or a 5- to 6-membered fully unsaturated heterocyclic ring, each ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from up to 2 O, up to 2 S and up to 3 N atoms, wherein up to 2 carbon ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 5 substituents independently selected from R 3a on carbon atom ring members and R 3b on nitrogen atom ring members;

R 1 is C 1 -C 2 alkyl, halomethyl, cyanomethyl or cyclopropyl;

R 2 is H, halogen, cyano, C 1 -C 2 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 2 haloalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 2 hydroxyalkyl, cyclopropyl, halocyclopropyl, C 2 -C 3 alkoxyalkyl, C 1 -C 2 alkylthio, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

each R 3a is independently halogen, cyano, hydroxy, nitro, amino, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 6 alkylcycloalkyl, C 4 -C 6 cycloalkylalkyl, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylsulfonyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 haloalkylsulfonyloxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 4 alkylcarbonyl, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino, C 2 -C 4 alkylcarbonylamino, —CH(═O), —NHCH(═O), —SF 5 , —SC≡N or -U—V-T;

each R 3b is independently cyano, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylaminoalkyl, C 3 -C 4 dialkylaminoalkyl, C 1 -C 3 alkoxy, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl;

R 4 is halogen, —OR 7 or —SC≡N;

R 5 is H or C 1 -C 4 alkyl;

R 7 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 cyanoalkyl, C 2 -C 6 alkoxyalkyl, —CH(═O), —S(═O) 2 OM 1 or —C(═W)R 9 ;

R 9 is C 1 -C 6 alkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylaminoalkyl, C 3 -C 6 dialkylaminoalkyl, C 2 -C 6 alkylthioalkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio;

each U is independently 0, S(═O) n , N(R 10 ) or a direct bond;

each V is independently C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 3 -C 6 alkynylene, C 3 -C 6 cycloalkylene or C 3 -C 6 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, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy;

each T is independently cyano, N(R 11a )(R 11b ), OR 12 or S(═O) n R 12 ;

each R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 (alkylthio)carbonyl, C 2 -C 6 alkoxy(thiocarbonyl), C 4 -C 8 cycloalkylcarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 4 -C 8 (cycloalkylthio)carbonyl or C 4 -C 8 cycloalkoxy(thiocarbonyl);

each R 11a and R 11b is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 (alkylthio)carbonyl, C 2 -C 6 alkoxy(thiocarbonyl), C 4 -C 8 cycloalkylcarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 4 -C 8 (cycloalkylthio)carbonyl or C 4 -C 8 cycloalkoxy(thiocarbonyl); or

a pair of R 11a and R 11b are taken together with the nitrogen atom to which they are attached to form a form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R 13 ;

each R 12 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 (alkylthio)carbonyl, C 2 -C 6 alkoxy(thiocarbonyl), C 4 -C 8 cycloalkylcarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 4 -C 8 (cycloalkylthio)carbonyl or C 4 -C 8 cycloalkoxy(thiocarbonyl);

each R 13 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy;

W is O or S;

M 1 is K, Na or Li; and

each n is independently 0, 1 or 2;

provided that when Q 2 is a phenyl ring which is not substituted with R 3a at either ortho position, then Q 1 is substituted by at least one R 3a at an ortho position.

2. A compound of claim 1 wherein:

Q 1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 3a ;

Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 3a ; or a pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl ring, each ring optionally substituted with up to 3 substituents independently selected from R 3a on carbon atom ring members and R 3b on nitrogen atom ring members;

R 1 is C 1 -C 2 alkyl, —CH 2 F, —CH 2 Cl or cyclopropyl;

R 2 is H, halogen, cyano, C 1 -C 2 alkyl, C 2 -C 4 alkenyl, halomethyl, cyanomethyl, hydroxymethyl, C 2 -C 3 alkoxyalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

each R 3a is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, cyclopropyl, C 1 -C 2 alkoxy, C 1 -C 2 alkylthio, C 2 -C 3 alkylcarbonyl or

—U—V-T;

each R 3b is independently cyano, C 1 -C 2 alkyl, cyclopropyl or C 2 -C 3 alkoxyalkyl;

R 4 is Br, Cl, F, —OR 7 or —SC≡N;

R 5 is H or methyl;

R 7 is H, C 1 -C 3 alkyl, C 2 -C 6 alkenyl, C 1 -C 3 haloalkyl, cyclopropyl, C 2 -C 3 cyanoalkyl, C 2 -C 6 alkoxyalkyl, —S(═O) 2 OM 1 or —C(═W)R 9 ;

R 9 is methyl or methoxy;

each U is independently O, N(R 10 ) or a direct bond;

each R 10 is independently H or methyl;

each V is independently C 1 -C 3 alkylene, wherein up to 1 carbon atom is selected from C(═O);

each T is independently N(R 11a )(R 11b b) or OR 12 ;

each R 11a and R 11b is independently H or methyl;

each R 12 is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

W is O; and

M 1 is Na or K.

3. A compound of claim 2 wherein:

Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 3a ; or a pyrazolyl, imidazolyl or pyridinyl ring, each ring optionally substituted with 1 to 3 substituents independently selected from R 3a on carbon atom ring members and R 3b on nitrogen atom ring members;

R 1 is methyl, —CH 2 F or —CH 2 Cl;

R 2 is halogen, cyano, C 1 -C 2 alkyl, halomethyl, cyanomethyl, hydroxymethyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

each R 3a is independently halogen, cyano, methyl, halomethyl, cyclopropyl, methoxy, methylthio, methylcarbonyl or —U—V-T;

each R 3b is methyl;

R 4 is Br, Cl, F or —OR 7 ;

R 7 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, —S(═O) 2 OM 1 or —C(═W)R 9 ;

each U is independently O, NH or a direct bond;

each V is C 1 -C 3 alkylene; and

each R 12 is independently H, methyl or halomethyl.

4. A compound of claim 3 wherein:

Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 3a ;

R 1 is methyl;

R 2 is halogen, cyano, methyl, halomethyl or methoxy;

each R 3a is independently halogen, cyano, methyl, halomethyl or methoxy;

R 4 is —OR 7 ;

R 5 is H;

R 7 is H, methyl or —C(═W)R 9 ; and

R 9 is methyl.

5. A compound of claim 4 wherein:

R 2 is Br, Cl, methyl or methoxy;

each R 3a is independently halogen, cyano or methoxy; and

R 7 is H.

6. A compound of claim 5 wherein:

R 2 methyl;

each R 3a is independently Br, Cl, F, cyano or methoxy; and

one of Q 1 and Q 2 is substituted with 2 to 3 substituents and the other of Q 1 and Q 2 is substituted with 1 to 2 substituents.

7. The compound of claim 1 which is selected from the group:

α-(2-chloro-4-fluorophenyl)-5-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

(αS)-α-(2-chloro-4-fluorophenyl)-5-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

(αR)-α-(2-chloro-4-fluorophenyl)-5-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-fluorophenyl)-5-(2,6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

(αS)-α-(2-chloro-4-fluorophenyl)-5-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

(αR)-α-(2-chloro-4-fluorophenyl)-5-(2,6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α,5-bis(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

5-(2-bromophenyl)-α-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-fluorophenyl)-5-(2,6-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-fluorophenyl)-1,3-dimethyl-5-(2,4,6-trifluorophenyl)-1H-pyrazole-4-methanol;

α-(2-bromo-4-fluorophenyl)-5-(2,6-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α-(2-bromo-4-fluorophenyl)-5-(2-chloro-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

3-bromo-5-(2-chloro-4-fluorophenyl)-α-(2,4-difluorophenyl)-1-methyl-1H-pyrazole-4-methanol;

5-(2-chloro-4-fluorophenyl)-α-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

5-(2,4-dichlorophenyl)-α-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

5-(2-chloro-6-fluorophenyl)-α-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

α-(2,4-difluorophenyl)-5-(2,6-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

4-[4-[(2,4-difluorophenyl)hydroxymethyl]-1,3-dimethyl-1H-pyrazol-5-yl]-3,5-difluorobenzonitrile;

5-(2-chloro-6-fluorophenyl)-α-(2,4-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

5-(2-chloro-6-fluorophenyl)-α-(2,6-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-α-(2,4,6-trifluorophenyl)-1H-pyrazole-4-methanol;

5-(2-bromo-4-fluorophenyl)-1,3-dimethyl-α-(2,4,6-trifluorophenyl)-1H-pyrazole-4-methanol;

5-(2-chloro-6-fluorophenyl)-α-(2-chloro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-4-methanol;

3-bromo-α-(2-chloro-4-fluorophenyl)-5-(2,6-difluorophenyl)-1-methyl-1H-pyrazole-4-methanol;

3-chloro-α-(2-chloro-4-fluorophenyl)-5-(2,6-difluorophenyl)-1-methyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-fluorophenyl)-5-(2,6-difluorophenyl)-3-methoxy-1-methyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-fluorophenyl)-5-(2-chloro-6-fluorophenyl)-3-methoxy-1-methyl-1H-pyrazole-4-methanol;

5-(2,6-difluorophenyl)-α-(4-fluoro-2-methylphenyl)-3-methoxy-1-methyl-1H-pyrazole-4-methanol;

α-(2-chloro-4-methoxphenyl)-5-(2,6-difluorophenyl)-3-methoxy-1-methyl-1H-pyrazole-4-methanol;

5-(2,6-difluorophenyl)-3-methoxy-α-(4-methoxy-2-methylphenyl)-1-methyl-1H-pyrazole-4-methanol;

5-(2-chloro-6-fluorophenyl)-α-(2-chloro-4-methoxyphenyl)-3-methoxy-1-methyl-1H-pyrazole-4-methanol;

3-chloro-5-(2,6-difluorophenyl)-α-(4-methoxy-2-methylphenyl)-1-methyl-1H-pyrazole-4-methanol;

3-chloro-5-(2,6-difluorophenyl)-α-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-4-methanol;

3-chloro-α-(2-chloro-4-methoxyphenyl)-5-(2,6-difluorophenyl)-1-methyl-1H-pyrazole-4-methanol; and

3-bromo-5-(2,6-difluorophenyl)-α-(4-methoxy-2-methylphenyl)-1-methyl-1H-pyrazole-4-methanol.

8. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one other fungicide.

9. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

10. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of claim 1 .