FUNGICIDAL PYRAZOLES

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

wherein

Q 1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered fully unsaturated 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 up 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 (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 on carbon atom ring members and selected from cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminoalkyl and C 3 -C 6 dialkylaminoalkyl on nitrogen atom ring members;

Q 2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered saturated, partially unsaturated or fully unsaturated 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 up 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 (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 on carbon atom ring members and selected from cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminoalkyl and C 3 -C 6 dialkylaminoalkyl on nitrogen atom ring members; or C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 3 -C 12 cycloalkyl or C 3 -C 12 cycloalkenyl, each optionally substituted with up to 5 substituents independently selected from R 3 ;

X is O, S(O) m , NR 4 , CR 15 R 16 , C(═O) or C(═S);

R 1 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 7 cycloalkyl, CO 2 R 5 , C(O)NR 6 R 7 , cyano, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 2 -C 5 alkoxyalkyl; or

R 1 is phenyl optionally substituted with up to 3 R 8 ; or a five- or six-membered nitrogen-containing aromatic heterocycle optionally substituted with up to 3 substituents independently selected from R 9a on carbon atom ring members and R 9b on nitrogen atom ring members;

R 1a is H; or

R 1a and R 1 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;

R 2 is CH 3 , CH 2 CH 3 , halogen, cyano, cyanomethyl, halomethyl, hydroxymethyl, methoxy or methylthio; or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl;

each R 3 is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, formylamino, C 2 -C 3 alkylcarbonylamino, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, 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 2 alkylsulfonyloxy, C 1 -C 2 haloalkylsulfonyloxy, C 3 -C 4 cycloalkyl, C 3 -C 7 cycloalkoxy, C 4 -C 6 alkylcycloalkyl, C 4 -C 6 cycloalkylalkyl, C 3 -C 7 halocycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, hydroxy, formyl, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkylcarbonyloxy, —SF 5 , —SCN, C(═S)NR 19 R 20 or —U—V-T;

R 4 is H, formyl, C 2 -C 5 alkenyl, C 3 -C 5 alkynyl, C 3 -C 7 cycloalkyl, —SO 3 -M + , —S(═O) t R 10 , —(C═W)R 11 , NH 2 or OR 21 ; or C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each optionally substituted with up to 2 R 12 ;

R 5 is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 6 and R 7 are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl and C 4 -C 8 alkylcycloalkyl; or

R 6 and R 7 are taken together with the nitrogen atom to which they are connected to form a four- to seven-membered nonaromatic heterocyclic ring containing ring members, in addition to the connecting ring nitrogen atom, selected from carbon atoms and optionally up to one ring member selected from O, S(O) n and NR 13 ;

each R 8 , R 9a and R 9b is independently selected from halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, cyano, nitro, SCH 3 , S(O)CH 3 and S(O) 2 CH 3 ;

R 10 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 11 is independently C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 7 alkylaminoalkyl, C 2 -C 8 dialkylaminoalkyl, C 1 -C 6 alkylthio or C 2 -C 7 alkylthioalkyl;

each R 12 is independently C 3 -C 7 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or cyano;

R 13 is H, C 1 -C 3 alkyl or C 2 -C 3 haloalkyl;

each R 14 is independently H, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 15 is H, C 1 -C 4 alkyl or OR 18 ;

R 16 is C 1 -C 4 alkyl or OR 18 ; or

R 15 and R 16 are taken together as —OCH 2 CH 2 O—;

each R 18 is independently H, formyl, C 3 -C 7 cycloalkyl, —SO 3 -M or —(C═W)R 11 ; or C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each optionally substituted with up to 2 R 12 ;

each R 19 and R 20 is independently H or CH 3 ;

R 21 is H, formyl, C 3 -C 7 cycloalkyl, —SO 3 -M or —(C═W)R 11 ; or C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each optionally substituted with up to 2 R 12 ;

each U is independently O, S(═O) w , NR 22 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, NR 23a R 23b , OR 24 or S(═O) y R 25

each R 22 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 23a and R 23b 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 23a and R 23b 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 R 26 ;

each R 24 and R 25 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 26 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy;

each W is independently O or S;

each M + is independently a cation;

m is 0, 1 or 2;

n is 0, 1 or 2;

t is 0, 1 or 2;

each u and v are independently 0, 1 or 2 in each instance of S(═O) u (═NR 14 ), provided that the sum of u and v is 0, 1 or 2;

each w is independently 0, 1 or 2; and

each y is independently 0, 1 or 2;

provided that:

when Q 2 is a phenyl ring substituted on at least one ortho position with a substituent selected from —U—V-T wherein U is a direct bond, V is C(═O) and T is NR 23a R 23b or OR 24 , then X is other than NR 4 .

2 . A compound of claim 1 wherein:

Q 1 is phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, each substituted with from 1 to 4 substituents independently selected from R 3 ; provided that when an R 3 substituent is located at a meta position, then said R 3 substituent is selected from F, Cl, Br and cyano;

Q 2 is phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 , provided that when an R 3 substituent is located at a meta position, then said R 3 substituent is selected from F, Cl, Br and cyano;

X is O, NR 4 , C(═O) or CR 15 R 16 ;

R 1 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, CO 2 R 5 , C(O)NR 6 R 7 , cyano, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 2 -C 5 alkoxyalkyl;

R 1a is H;

R 2 is CH 3 , CH 2 CH 3 , Cl or Br;

each R 3 is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy 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 3 -C 4 cycloalkyl, C(═S)NH 2 and —U—V-T;

R 4 is H, formyl, C 3 -C 7 cycloalkyl or —SR 10 ; or C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each optionally substituted with up to 2 R 12 ;

R 5 is C 1 -C 6 alkyl;

R 6 is H or C 1 -C 6 alkyl;

R 7 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 4 -C 8 alkylcycloalkyl; or

R 6 and R 7 are taken together with the nitrogen atom to which they are connected to form a four- to seven-membered nonaromatic heterocyclic ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to one ring member selected from O and NR 13 ;

each R 12 is independently C 3 -C 7 cycloalkyl, C 1 -C 4 alkoxy or cyano;

R 13 is H or CH 3 ;

R 15 is H or CH 3 ; and

R 16 is OR 18 .

3 . A compound of claim 2 wherein

Q 1 is phenyl or pyridinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 ;

Q 2 is phenyl or pyridinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 ;

R 1 is H, halogen or C 1 -C 6 alkyl;

R 2 is CH 3 , Cl or Br;

each R 3 is independently selected from halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy and —U—V-T;

R 4 is H, formyl, C 3 -C 7 cycloalkyl or —SR 10 ; or C 1 -C 6 alkyl substituted with one R 12 ;

each R 12 is independently cyclopropyl, —OCH 3 or cyano;

R 15 is H;

each U is independently O or NH;

each V is C 2 -C 4 alkylene;

each T is independently NR 23a R 23b or OR 24 ;

each R 23a and R 23b is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; and

each R 24 is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.

4 . A compound of claim 3 wherein

at least one of Q 1 and Q 2 is phenyl substituted with 2 or 3 substituents independently selected from R 3 ;

R 1 is H or CH 3 ;

R 2 is CH 3 ;

R 4 is H;

each R 3 is independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkoxy; and

R 18 is H.

5 . A compound of claim 4 wherein

Q 1 is phenyl substituted at the 2-, 4- and 6-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 4-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 6-positions with substituents independently selected from R 3 ;

Q 2 is phenyl substituted at the 2-, 4- and 6-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 4-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 6-positions with substituents independently selected from R 3 ;

X is O, NR 4 or CR 15 R 16 ;

R 1 is H;

each R 3 is independently selected from F, Cl, Br, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy; and

R 4 is H.

6 . A compound of claim 5 wherein

each R 3 is independently selected from F, Cl, Br, cyano, methyl, C 1 -C 2 alkoxy and fluoromethoxy.

7 . A compound of claim 6 wherein

X is O or NH; and

each R 3 is independently selected from F, Cl, Br, cyano and methoxy.

8 . A compound of claim 1 which is selected from the group:

4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine,

N-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine,

N-(2,6-difluoro-4-methoxyphenyl)-4-(3,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2,4-difluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine,

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

4-[[4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3-fluorobenzonitrile,

4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

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

3-chloro-4-[[4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile,

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

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

N-(2-chloro-4-fluorophenyl)-4-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-chloro-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-chloro-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(4-chloro-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(4-chloro-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

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

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

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

N-(2-chloro-4-fluorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

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

N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,

N-(2-chloro-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2,6-dichloro-4-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

3-chloro-4-[5-[(2-chloro-4,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-benzonitrile,

3-chloro-4-[5-[(4-chloro-2,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-benzonitrile,

N-(2-bromo-4-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2,4-dichloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2,6-dichloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-[[4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3-fluorobenzonitrile,

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

4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine,

N-(4-bromo-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-[[4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3,5-difluorobenzonitrile,

4-(2-bromo-4-fluorophenyl)-N-(2-chloro-4,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(4-chloro-2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(4-bromo-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

3-bromo-4-[[4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile,

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

N-(2,4-dichloro-6-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2,6-dichloro-4-fluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(4-bromo-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

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

4-[5-[(2-chloro-4,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-3-fluorobenzonitrile,

4-[5-[(4-chloro-2,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-3-fluorobenzonitrile,

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

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

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

9 . The compound of claim 1 which is 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine.

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

11 . 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.

12 . 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 .

13 . A composition comprising a compound of claim 1 , and at least one invertebrate pest control compound or agent.

14 . A compound of Formula 2 or a salt thereof

wherein

Q 1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered fully unsaturated 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 up 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 (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 on carbon atom ring members and selected from cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminoalkyl and C 3 -C 6 dialkylaminoalkyl on nitrogen atom ring members;

Q 2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered saturated, partially unsaturated or fully unsaturated 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 up 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 (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 on carbon atom ring members and selected from cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminoalkyl and C 3 -C 6 dialkylaminoalkyl on nitrogen atom ring members; or C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 3 -C 12 cycloalkyl or C 3 -C 12 cycloalkenyl, each optionally substituted with up to 5 substituents independently selected from R 3 ;

X is NH;

R 2 is CH 3 , CH 2 CH 3 , halogen, cyano, cyanomethyl, halomethyl, hydroxymethyl, methoxy or methylthio; or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl;

each R 3 is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, formylamino, C 2 -C 3 alkylcarbonylamino, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, 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 2 alkylsulfonyloxy, C 1 -C 2 haloalkylsulfonyloxy, C 3 -C 4 cycloalkyl, C 3 -C 7 cycloalkoxy, C 4 -C 6 alkylcycloalkyl, C 4 -C 6 cycloalkylalkyl, C 3 -C 7 halocycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, hydroxy, formyl, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkylcarbonyloxy, —SF 5 , —SCN, C(═S)NR 19 R 20 or —U—V-T;

each R 14 is independently H, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

each R 19 and R 20 is independently H or CH 3 ;

each U is independently O, S(═O) w , NR 22 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, NR 23a R 23b , OR 24 or S(═O) y R 25

each R 22 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 23a and R 23b 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 23a and R 23b 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 R 26 ;

each R 24 and R 25 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 26 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy;

each u and v are independently 0, 1 or 2 in each instance of S(═O) u (═NR 14 ) v , provided that the sum of u and v is 0, 1 or 2;

each w is independently 0, 1 or 2; and

each y is independently 0, 1 or 2;

provided that:

(a) when Q 2 is a phenyl ring substituted on at least one ortho position with a substituent selected from —U—V-T wherein U is a direct bond and T is NR 23a R 23b or OR 24 , then V is other than C(═O); and

(b) when Q 1 is phenyl and Q 2 is 4-(trifluoromethyl)phenyl, then R 2 is other than methyl.