FUNGICIDAL SUBSTITUTED HETEROCYCLES

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

wherein

J is selected from the group consisting of:

wherein the bond of J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-8 or J-9 which is identified with “a” is connected to Q 1 of Formula 1, and the bond which is identified with “b” is connected to Q 2 of Formula 1;

each W is independently 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 5 ; 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 5 ; 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 5 ;

R 1a and R 1b are each independently H, halogen, cyano, hydroxy, nitro, amino, C(═O)NR 6a R 6b , C(═O)OH, 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 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, 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 3 -C 6 halocycloalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 haloalkoxycarbonyloxy, 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 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 6 dialkylamino, C 2 -C 6 alkylcarbonylamino or C 2 -C 6 alkoxy carbonylamino;

R 2 is cyano, hydroxy, 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 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 3 is amino, cyano, hydroxy, 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 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl;

R 4 is cyano;

each R 5 is independently amino, cyano, halogen, hydroxy, nitro or -U-V-T; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 4 -C 6 cycloalkylalkyl, C 2 -C 6 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkoxy, C 2 -C 6 cyanoalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino or C 2 -C 6 dialkylamino, each optionally substituted with up to 5 substituents independently selected from halogen and C 1 -C 3 alkyl;

each R 6a and R 6b is independently H, 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 alkoxycarbonyl;

each U is independently a direct bond, O, C(═O) or NR 7 ;

each V is independently C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 3 -C 6 alkynylene, wherein up to 2 carbon atoms are C(═O), each optionally substituted with up to 3 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 NR 8a R 8b , OR 9 or S(═O) p R 10 ;

each p is independently 0, 1 or 2;

each R 7 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 8a and R 8b 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 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl; or

R 8a and R 8b are taken together with the nitrogen atom to which they are attached to form a 3- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 11 ;

each R 9 and R 10 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, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl; and

each R 11 is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;

provided that:

(a) when J is J-1, then at most only one of Q 1 and Q 2 is an optionally substituted phenyl ring;

(b) when J is J-8, then Q 1 is a phenyl ring substituted with at least one R 5 substituent at an ortho position, and Q 2 is an optionally substituted phenyl ring;

(c) the compound of Formula 1 is not:

5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2,6-bis(1-methylethoxy)pyrimidine,

5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2,6-diethoxypyrimidine,

5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2,6-dimethoxypyrimidine,

2,4-dichloro-5-(4-methoxyphenyl)-6-phenylpyrimidine,

2,4-dichloro-5-(4-chlorophenyl)-6-phenylpyrimidine,

2,4-dichloro-6-(4-chlorophenyl)-5-phenylpyrimidine,

2,4-dichloro-6-(4-methylphenyl)-5-phenylpyrimidine,

2,4-dichloro-5,6-diphenylpyrimidine,

4-chloro-6-(4-chlorophenyl)-5-(2,4,6-trifluorophenyl)pyrimidine,

4-chloro-6-(3-fluorophenyl)-5-(2,4,6-trifluorophenyl)pyrimidine,

4-chloro-6-(3,5-dimethoxyphenyl)-5-(2,4,6-trifluorophenyl)pyrimidine,

4-(4-chlorophenyl)-6-methyl-5-(2,4,6-trifluorophenyl)pyrimidine,

4-(3-fluorophenyl)-6-methyl-5-(2,4,6-trifluorophenyl)pyrimidine,

4-(3,5-dimethoxyphenyl)-6-methyl-5-(2,4,6-trifluorophenyl)pyrimidine,

4-(4-chlorophenyl)-5-(2,6-difluoro-4-methoxyphenyl)-6-methylpyrimidine,

5-(2,6-difluoro-4-methoxyphenyl)-4-(3-fluorophenyl)-6-methylpyrimidine and

5-(2,6-difluoro-4-methoxyphenyl)-4-(3,5-dimethoxyphenyl)-6-methylpyrimidine.

2 . A compound claim 1 wherein

J is J-1, J-2, J-4, J-6, J-7, J-8 or J-9;

W is O;

Q 1 and Q 2 are each independently selected from:

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

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

R 1a and R 1b are each independently H, halogen, cyano, C(═O)NR 6a R 6b , 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 3 -C 5 cycloalkyl, C 3 -C 5 halocycloalkyl, C 1 -C 3 hydroxyalkyl, 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, C 2 -C 3 haloalkynyloxy, C 3 -C 5 cycloalkoxy, C 1 -C 3 alkylamino or C 2 -C 3 dialkylamino;

R 2 is 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; or C 3 -C 5 cycloalkyl, optionally substituted with up to 3 substituents independently selected from halogen and methyl;

R 3 is cyano, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 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 or C 2 -C 6 cyanoalkoxy;

each R 5 is independently cyano, halogen, nitro or -U-V-T; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 cyanoalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkoxy, C 2 -C 6 cyanoalkoxy, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl, each optionally substituted with up to 3 substituents independently selected from halogen;

each R 6a and R 6b is independently H, methyl, trifluoromethyl, methoxy or methylcarbonyl;

each U is independently a direct bond, O, C(═O) or NH;

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

each T is independently NR 8a R 8b or OR 9 ;

each R 8a and R 8b is independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyclopropyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 alkoxycarbonyl; and

each R 9 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

J is J-1, J-2, J-4, J-6, J-8 or J-9;

Q 1 and Q 2 are each independently selected from A-1, A-2, A-4, A-19, A-25, A-28, A-31 and A-43;

each q is independently 1, 2 or 3;

R 1a and R 1b are each independently H, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyclopropyl, C 1 -C 3 hydroxyalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;

R 2 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; or cyclopropyl, optionally substituted with up to 2 substituents independently selected from halogen and methyl;

R 3 is cyano, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 2 -C 6 cyanoalkoxy;

each R 5 is independently cyano, halogen, nitro or -U-V-T; or C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyloxy, C 2 -C 3 alkynyloxy, C 3 -C 6 cycloalkoxy or C 2 -C 3 cyanoalkoxy, each optionally substituted with up to 3 substituents independently selected from halogen;

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

each V is independently CH 2 , CH 2 CH 2 , C(═O), CH 2 C(═O) or C(═O)CH 2 ;

each R 8a and R 8b is independently H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or cyclopropyl; and

each R 9 is independently methyl or ethyl.

4 . A compound of claim 3 wherein

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

R 1a and R 1b are each independently H, halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, cyclopropyl or C 1 -C 2 hydroxyalkyl;

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

R 3 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy; and

each R 5 is independently cyano, halogen, nitro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 2 -C 3 alkenyloxy or C 2 -C 3 cyanoalkoxy, each optionally substituted with up to 3 substituents independently selected from halogen.

5 . A compound of claim 4 wherein

J is J-2, J-4, J-6 or J-8;

Q 1 and Q 2 are each A-1;

each q is independently 2 or 3;

R 1a and R 1b are each independently H, Br, Cl, F, cyano, methyl, ethyl or CH 2 F;

R 2 is methyl, ethyl or methoxy;

R 3 is methyl or ethyl; and

each R 5 is independently cyano, halogen, nitro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy or C 2 -C 3 cyanoalkoxy.

6 . A compound of claim 5 wherein

R 1a and R 1b are each independently Br, Cl, F, methyl or ethyl;

R 2 is methyl or ethyl; and

each R 5 is independently cyano, Br, Cl, F, methyl or methoxy.

7 . A compound of claim 6 wherein

R 1a and R 1b are each independently Br, Cl, methyl or ethyl;

R 2 is methyl; and

each R 5 is independently Br, Cl, F, methyl or methoxy.

8 . A compound of claim 7 wherein

J is J-2, J-6 or J-8;

R 1a and R 1b are each independently Br, Cl or methyl;

each R 5 is independently Br, Cl, F or methoxy.

9 . A compound of any-ene claims 1-4 wherein

J is J-2, J-4, J-6 or J-8; and

Q 1 and Q 2 are each A-1.

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

6-(2,4-difluorophenyl)-1-(3,5-dimethoxyphenyl)-3,5-dimethyl-4(1H)-pyridazinone;

1-(2-chloro-3,5-dimethoxyphenyl)-6-(2,4-difluorophenyl)-3,5-dimethyl-4(1H)-pyridazinone;

5-chloro-1-(2-chloro-3,5-dimethoxyphenyl)-6-(2-chloro-4-fluorophenyl)-3-methyl-2,4(1H,3H)-pyrimidinedione;

4-(2-chloro-3,5-dimethoxyphenyl)-5-(2-chloro-4-fluorophenyl)-2,6-dimethylpyrimidine;

2-chloro-4-(2-chloro-3,5-dimethoxyphenyl)-5-(2-chloro-4-fluorophenyl)-6-methylpyrimidine;

4-(2-chloro-3,5-dimethoxyphenyl)-2,6-dimethyl-5-(2,4,6-trifluorophenyl)pyrimidine;

4-(2-chloro-3,5-dimethoxyphenyl)-5-(2-chloro-4-fluorophenyl)-6-ethyl-2-methylpyrimidine;

4-(2-chloro-3,5-dimethoxyphenyl)-5-(2,6-difluorophenyl)-6-ethyl-2-methylpyrimidine;

4-(2-bromo-3,5-dimethoxyphenyl)-2,6-dimethyl-5-(2-chloro-4-fluorophenyl)pyrimidine;

5-(2-chloro-3,5-dimethoxyphenyl)-1,2-dihydro-1-methyl-2-oxo-6-(2,4,6-trifluorophenyl)-3-pyridinecarbonitrile;

1,2-dihydro-5-(3,5-dimethoxyphenyl)-1-ethyl-2-oxo-6-(2,4,6-trifluorophenyl)-3-pyridinecarbonitrile;

5-(2-chloro-3,5-dimethoxyphenyl)-1,2-dihydro-1-ethyl-2-oxo-6-(2,4,6-trifluorophenyl)-3-pyridinecarbonitrile;

3-chloro-6-(2-chloro-4-fluorophenyl)-1-(2-chloro-3,5-dimethoxyphenyl)-5-methyl-4(1H)-pyridazinone;

3-bromo-6-(2-chloro-4-fluorophenyl)-1-(2-chloro-3,5-dimethoxyphenyl)-5-methyl-4(1H)-pyridazinone;

6-(2-chloro-4-fluorophenyl)-3,5-dimethyl-1-(3,5-dimethoxyphenyl)-4(1H)-pyridazinone;

5-chloro-1-(2-chloro-5-methoxyphenyl)-6-(4-fluorophenyl)-3-methyl-4(1H)-pyridazinone;

5-chloro-1-(2-chloro-5-methoxyphenyl)-6-(2-chloro-4-fluorophenyl)-3-methyl-4(1H)-pyridazinone;

5-bromo-1-(2-chloro-5-methoxyphenyl)-6-(2-chloro-4-fluorophenyl)-3-methyl-4(1H)-pyridazinone;

5-(2-chloro-3,5-dimethoxyphenyl)-6-(2-chloro-4-fluorophenyl)-1,2-dihydro-1-methyl-2-oxo-3-pyridinecarbonitrile; and

5-(2-chloro-3,5-dimethoxyphenyl)-6-(2-chloro-4-fluorophenyl)-1,2-dihydro-1-ethyl-2-oxo-3-pyridinecarbonitrile.

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 .