Fungicidal heterocyclic carboxamides

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

wherein

A is a radical selected from the group consisting of

R 1 is H, cyclopropyl or C 1 -C 2 alkoxy;

Z is O or S;

L is —C(R 12a )R 12b —C(R 13a )R 13b —, wherein the carbon atom bonded to R 12a and R 12b is also bonded to the carboxamide nitrogen atom in Formula 1; or 1,2-phenylene optionally substituted with up to 4 substituents independently selected from halogen and C 1 -C 2 alkyl;

G is N or C—R 2a ;

each R 2 is independently halogen, nitro, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

n is 0, 1, 2 or 3;

R 2a is H, halogen, nitro, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

B 1 is CH or N;

B 2 is CH or N;

R 3 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 4 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 5 is H, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 6 is C 1 -C 2 alkyl;

R 7 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 8 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

R 9 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 10 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 11 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

m is 0, 1 or 2;

R 12a and R 12b are each independently H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

R 12a and R 12b are taken together as C 2 -C 4 alkanediyl;

R 13a is H, halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 alkoxyamino;

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

R 13a and R 13b are taken together as C 2 -C 4 alkanediyl;

Q is a 5-membered unsaturated heterocyclic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 1O, up to 1S and up to 4N atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O), the ring optionally substituted with one substituent on a ring member distal relative to the ring member connecting the heteroaromatic ring to the remainder of Formula 1, said optional substituent selected from R 14c on carbon atom ring members and from R 14n on nitrogen atom ring members, the heterocyclic ring further optionally substituted with substituents selected from R 15c on carbon atom ring members and R 15n on nitrogen atom ring members;

each R 14c is independently halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkoxycarbonyl or C 2 -C 4 alkylcarbonyl; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 16 ; or a heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R 17c on carbon atom ring members and from R 17n on nitrogen atom ring members;

each R 14n is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 18 ; or a heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R 19c on carbon atom ring members and from R 19n on nitrogen atom ring members;

each R 15c is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy;

each R 15n is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy;

each R 16 , R 17c , R 18 and R 19c is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

each R 17n and R 19n is independently C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

R 20 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 21 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; and

R 22 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

provided that the compound of Formula 1 is other than: 2-methyl-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]-5-thiazolecarboxamide, N-[2-[4-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethyl]-1,3,5-trimethyl-1H-pyrazole-4-carboxamide, 2-bromo-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]benzamide, 3-methyl-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]-2-thiophenecarboxamide, 2-methyl-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]benzamide, 2-iodo-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]benzamide, 2-fluoro-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]benzamide, 2-chloro-N-[2-[4-(1H-pyrazol-1-yl)phenyl]ethyl]benzamide, 5-chloro-1,3-dimethyl-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]-1H-pyrazole-4-carboxamide, 2-methyl-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]benzamide, 2-methyl-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]-3-furancarboxamide, 2-fluoro-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]benzamide, 2-bromo-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]benzamide, 2-iodo-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]benzamide, N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]-2-(trifluoromethyl)benzamide, and 2-chloro-N-[2-[4-(2-methyl-4-thiazolyl)phenyl]ethyl]benzamide.

2. A compound of claim 1 wherein:

Z is O;

L is —C(R 12a )R 12b —C(R 13a )R 13b —; or 1,2-phenylene optionally substituted with up to 2 substituents independently selected from F, Cl, Br and CH 3 ;

each R 2 is independently F, Cl, Br or CH 3 ;

R 2a is H, F, Cl, Br or CH 3 ;

R 3 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 4 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 5 is H, F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 6 is CH 3 ;

R 7 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 8 is H or CH 3 ;

R 9 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 10 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 11 is F, Cl Br, CH 3 , CHF 2 or CF 3 ;

R 12a is H or CH 3 ;

R 12b is H;

R 13a is H, CH 3 , or OCH 3 ;

R 13b is H;

each R 16 , R 17c ; R 18 and R 19c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ; and

each R 17n and R 19n is CH 3 .

3. A compound of claim 2 wherein:

A is A-1, A-2, A-3 or A-4;

each R 14c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ;

each R 14n is CH 3 ;

each R 15c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ; and

each R 15n is CH 3 .

4. A compound of claim 3 wherein:

A is A-1, A-2 or A-4;

B 2 is N; and

Q is Q-9A or Q-9B.

5. A compound of claim 4 wherein:

L is —C(R 12a )R 12b —C(R 13a )R 13b —;

R 2a is H, F or Cl; and

each R 2 is F or Cl;

provided that when G is N or R 2a is H, then the ring comprising G is substituted with R 2 ortho to the bond to L.

6. A compound of claim 4 wherein:

L is 1,2-phenylene optionally substituted with up to 2 substituents independently selected from F, Cl, Br and CH 3 ;

R 2a is H, F or Cl;

each R 2 is F or Cl; and

the ring comprising G is substituted with at least one R 2 ortho to the bond to Q.

7. A compound of claim 1 , provided that when G is N or R 2a is H, then the ring comprising G is substituted with at least one instance of R 2 .

8. A compound of claim 1 wherein L is —C(R 12a )R 12b —C(R 13a )R 13b —.

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

3-chloro-N-[2-chloro-4-(3-trifluoromethyl)-1H-pyrazol-1-yl]phenyl-1-methylethyl]-2-pyrazinecarboxamide,

N-[2-[2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethyl-3-(trifluoromethyl)-2-pyridinecarboxamide,

N-[3′,5′-difluoro-4′-[3-(trifluoromethyl)-1H-pyrazol-1-yl][1,1′-biphenyl]-2-yl]-3-(trifluoromethyl)-2-pyridinecarboxamide,

3-(difluoromethyl)-N-[3′,5′-difluoro-4′-[3-(trifluoromethyl)-1H-pyrazol-1-yl][1,1′-biphenyl]-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, and

N-[2-[3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinyl]ethyl]-2-(trifluoromethyl)benzamide.

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 protecting a plant or plant seed from diseases caused by fungal pathogens comprising applying a fungicidally effective amount of a compound of claim 1 to the plant or plant seed.

13. A method for controlling a phytophagous nematode comprising contacting the nematode or its environment with a nematocidally effective amount of a compound of claim 8 .