Fungicidal pyrazoles

1. A compound selected from Formula 1A, 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 3 substituents independently selected from R 3a ;

X is O, S(O) m , N(R 6 ) or C(═O);

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;

R 6 is H, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 cyanoalkyl, NH 2 , —CH(═O), —OR 7 , —OS(═O) 2 M 1 , —S(═O) n R 8 or —C(═W)R 9 ;

R 7 is 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 8 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

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 O, 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;

m is 0, 1 or 2; and

each n is independently 0, 1 or 2;

provided that:

(a) 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; and

(b) the compound is other than 1-[2-[4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]phenyl]ethanone.

2. A compound of claim 1 wherein:

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

X is O, S, N(R 6 ) or C(═O);

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;

R 6 is H, hydroxy, —CH(═O), C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkoxyalkyl, —OR 7 , —OS(═O) 2 M 1 , —S(═O) n R 8 or —C(═W)R 9 ;

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 8 is methyl;

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 ) 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:

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;

R 6 is H, methyl, halomethyl 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:

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 7 is H, methyl or —C(═W)R 9 ; and

R 9 is methyl.

5. A compound of claim 4 wherein:

X is O, S, NH or C(═O);

R 2 is Br, Cl, methyl or methoxy; and

each R 3a is independently halogen, cyano or methoxy.

6. A compound of claim 5 wherein:

R 2 is 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:

5-(2-chloro-4-methoxyphenyl)-4-(2,4-difluorophenoxy)-1,3-dimethyl-1H-pyrazole;

4-(2-chloro-4-fluorophenoxy)-5-(2-chloro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole;

3-chloro-4-[4-(2-chloro-4-fluorophenoxy)-1,3-dimethyl-1H-pyrazol-5-yl]benzonitrile;

4-[[5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]amino]-3,5-difluorobenzonitrile;

N,5-bis(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine;

3-chloro-4-[[5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]oxy]benzonitrile;

5-(2-chloro-4-fluorophenyl)-N-(2,4-dichlorophenyl)-1,3-dimethyl-1H-pyrazole-4-amine;

5-(2-chloro-4-fluorophenyl)-N-(4-chloro-2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-amine;

4-(2-chloro-4-fluorobenzoyl)-5-(2,4-difluorophenyl)-1-methyl-1H-pyrazole-3-carbonitrile;

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

N-(2,4-dichlorophenyl)-5-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine; and

[5-(2,4-dichlorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl](2,4-difluorophenyl)methanone.

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 .