FUNGICIDAL PYRIDONES

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

wherein

W is O or S;

Q 1 and Q 2 are each independently a phenyl ring optionally substituted with up to 5 substituents independently selected from R 4 ; or a 5- to 6-membered heteroaromatic ring, each ring 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, each ring optionally substituted with up to 5 substituents independently selected from R 4 ; or a 3- to 6-membered nonaromatic heterocyclic ring, each ring 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 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O) 2 , each ring optionally substituted with up to 5 substituents independently selected from R 4 ;

R 1 is amino, cyano, hydroxy, NH 2 C(═O)H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 cyanoalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 cyanoalkoxy, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 6 dialkylamino, C 4 -C 8 alkylcarbonylamino, C 2 -C 6 alkoxyalkylamino, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl; or C 3 -C 6 cycloalkyl or C 4 -C 6 cycloalkylalkyl, each optionally substituted with up to 3 substituents independently selected from halogen, cyano and C 1 -C 3 alkyl;

R 2 is H, halogen, cyano, hydroxy, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 cyanoalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkoxyalkoxy or C 2 -C 6 haloalkoxyalkoxy; or C 3 -C 6 cycloalkyl or C 4 -C 6 cycloalkylalkyl, each optionally substituted with up to 3 substituents independently selected from halogen, cyano and C 1 -C 3 alkyl;

R 3 is H, halogen, amino, cyano, hydroxy, nitro, C(═O)H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl or C 2 -C 6 alkoxycarbonyl; or a 3- to 6-membered nonaromatic ring containing ring members selected from carbon atoms and optionally up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 5 substituents independently selected from R 5 ;

each R 4 is independently halogen, cyano, nitro, amino, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 6 alkylcycloalkyl, C 4 -C 6 cycloalkylalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 4 haloalkylcarbonyloxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 haloalkylsulfonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 6 dialkylamino or -U-V-T;

each R 5 is independently halogen, cyano, hydroxy, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkylcarbonyloxy;

each U is independently a direct bond, O, S(═O) m or NR 6 ;

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 2 carbon atoms are 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 7a R 7b , OR 8 or S(═O) m R 9 ;

each R 6 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 (alkylthio)carbonyl or C 2 -C 6 alkoxy(thiocarbonyl);

each R 7a and R 7b is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl; or

R 7a and R 7b 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 3 substituents independently selected from R 10 ;

each R 8 and R 9 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl or C 2 -C 6 alkoxycarbonyl;

each R 10 is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; and

each m is independently 0, 1 or 2.

provided that:

(a) when Q 1 is an optionally substituted phenyl ring, then Q 2 is other than an optionally substituted 1H-pyrazol-4-yl ring; and

(b) the compound of Formula 1 is not:

3,6-dichloro-1-methyl-4,5-diphenyl-2(1H)-pyridinone;

1-methyl-4,5-diphenyl-2(1H)-pyridinone;

1-[5-[1-(cyclopropylmethyl)-1H-pyrazol-4-yl]-1,2-dihydro-1-methyl-2-oxo-4-pyridinyl]-1H-pyrrole-3-carboxylic acid;

1-[1,2-dihydro-1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-2-oxo-4-pyridinyl]-1H-pyrrole-3-carboxylic acid;

1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-4-(1H-pyrrol-1-yl)-2(1H)-pyridinone,

1-amino-3,6-dimethyl-4,5-diphenyl-2(1H)-pyridinone,

methyl (3,6-dimethyl-2-oxo-4,5-diphenyl-1(2H)-pyridinyl)carbamate, or

ethyl (3,6-dimethyl-2-oxo-4,5-diphenyl-1(2H)-pyridinyl)carbamate.

2 . A compound claim 1 wherein

W is O;

Q 1 and Q 2 are each independently selected from A-1 through A-47

wherein the floating bond is connected to Formula 1 through any available carbon or nitrogen atom of the depicted ring; and

each n is independently 0, 1, 2, 3 or 4;

R 1 is cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkenyloxy, C 2 -C 3 haloalkenyloxy, C 2 -C 3 alkynyloxy or C 2 -C 3 cyanoalkoxy; or cyclopropyl optionally substituted with up to 3 substituents independently selected from halogen and methyl;

R 2 is H, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl, C 2 -C 3 alkynyl, C 2 -C 3 haloalkynyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; or cyclopropyl optionally substituted with up to 3 substituents independently selected from halogen, cyano and methyl;

R 3 is H, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; or a 3- to 6-membered nonaromatic ring containing ring members selected from carbon atoms and optionally up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 3 substituents independently selected from R 5 ;

each R 4 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyloxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 4 haloalkylcarbonyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or -U-V-T;

each R 5 is independently halogen, cyano, methyl, halomethyl or methoxy;

each U is independently a direct bond, O or NR 6 ;

each V is independently C 1 -C 3 alkylene, wherein up to 1 carbon atom is C(═O), optionally substituted with up to 2 substituents independently selected from halogen, methyl, halomethyl and methoxy;

each T is independently NR 7a R 7b or OR 8 ;

each R 6 is independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkylcarbonyl;

each R 7a and R 7b is independently H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or cyclopropyl; and

each R 8 is independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl or cyclopropyl.

3 . A compound of claim 2 wherein

Q 1 and Q 2 are each independently selected from A-1, A-2, A-3, A-4, A-5, A-6, A-7 and A-19;

R 1 is cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkenyloxy, C 2 -C 3 haloalkenyloxy, C 2 -C 3 alkynyloxy or C 2 -C 3 cyanoalkoxy;

R 2 is H, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;

R 3 is H, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;

each R 4 is independently halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl C 2 -C 3 haloalkenyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or -U-V-T;

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

each V is independently CH 2 or CH 2 CH 2 ;

each R 7a and R 7b is independently H, methyl or halomethyl; and

each R 8 is independently H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl.

4 . A compound of claim 3 wherein

Q 1 and Q 2 are each independently selected from A-1, A-4, A-5 and A-19;

each n is independently 1, 2 or 3;

R 1 is C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

R 2 is H, halogen, cyano or C 1 -C 2 alkyl;

R 3 is H, halogen or C 1 -C 2 alkyl; and

each R 4 is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy.

5 . A compound of claim 4 wherein

Q 1 and Q 2 are each 1-A;

each n is independently 2 or 3;

R 1 is C 1 -C 2 alkyl or C 1 -C 2 alkoxy;

R 2 is halogen, cyano, methyl or ethyl;

R 3 is H, Br, Cl or methyl; and

each R 4 is independently halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy.

6 . A compound of claim 5 wherein

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

R 1 is methyl; and

each R 4 is independently Br, Cl, F, methyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy.

7 . A compound of claim 6 wherein

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

R 2 is halogen, methyl or ethyl;

R 3 is H; and

each R 4 is independently Br, Cl, F, methyl, methoxy or ethoxy.

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

3-chloro-5-(2-chloro-3,5-dimethoxyphenyl)-4-(2-chloro-4-fluorophenyl)-1-methyl-2(1H)-pyridinone;

5-(2-bromo-3,5-dimethoxyphenyl)-3-chloro-4-(2,4-difluorophenyl)-1-methyl-2(1H)-pyridinone;

5-(2-chloro-3,5-dimethoxyphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-2(1H)-pyridinone;

5-(2-bromo-5-methoxyphenyl)-3-chloro-4-(2,4-difluorophenyl)-1-methyl-2(1H)-pyridinone;

3-chloro-5-(2-chloro-3,5-dimethoxyphenyl)-4-(2,4-difluorophenyl)-1-methyl-2(1H)-pyridinone;

3-chloro-5-(2-chloro-5-methoxyphenyl)-4-(2,4-difluorophenyl)-1-methyl-2(1H)-pyridinone;

3-chloro-4-(2-chloro-4-fluorophenyl)-5-(2-chloro-5-methoxyphenyl)-1-methyl-2(1H)-pyridinone;

3-bromo-4-(2-chloro-4-fluorophenyl)-5-(2-chloro-5-methoxyphenyl)-1-methyl-2(1H)-pyridinone;

4-(2-chloro-4-fluorophenyl)-5-(2-chloro-5-methoxyphenyl)-1,3-dimethyl-2(1H)-pyridinone;

3-chloro-4-(2,4-difluorophenyl)-5-(2-fluoro-3,5-dimethoxyphenyl)-1-methyl-2(1H)-pyridinone;

5-(2-chloro-5-methoxyphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-2(1H)-pyridinone; and

5-(2-bromo-5-methoxyphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-2(1H)-pyridinone.

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 .