Fungicidal oxadiazoles

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

wherein

R 1 is

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

x is 0, 1 or 2;

L is (CR 4a R 4b ) n , OCH 2 , CH 2 O, OCH 2 CH 2 , CH 2 CH 2 O or CH 2 OCH 2 ; wherein the atom to the left is connected to R 1 , and the atom to the right is connected to J;

J is

wherein the bond projecting to the left is bonded to L, and the bond projecting to the right is bonded to the oxadiazole ring in Formula 1;

each R 5a is independently H or R 5 ; provided that at most only two R 5a substituents are other than H;

each R 2 is independently halogen, cyano, —CH(═O), —C(═O)OH, —C(═O)NR 3a R 3b , —C(R 6 )═NR 7 or —U—V-Q; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 7 cycloalkoxy, C 1 -C 6 alkylthio, C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, C 4 -C 7 cycloalkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy or C 2 -C 6 alkylcarbonylamino, each optionally substituted with up to 2 substituents independently selected from R 10 ;

each R 3a is independently H, cyano, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 3 -C 5 alkoxycarbonylalkyl;

each R 3b 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 8 halocycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from cyano, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl and C 3 -C 15 trialkylsilyl;

each R 4a and R 4b is independently H, halogen, methyl or methoxy;

each R 5 is methoxy;

each R 6 is independently H or methyl;

each R 7 is independently C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy or C 2 -C 4 alkynyloxy, each optionally substituted with up to 1 substituent selected from cyano, hydroxy and —C(═O)OH;

each R 10 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkoxy, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl or —C(R 13 )═NOR 14 ;

each U is independently a direct bond, C(═O)O or C(═O)NR 17 , wherein the atom to the left is connected to R 1 , and the atom to the right is connected to V;

each V is independently a direct bond, C 1 -C 3 alkylene, C 2 -C 4 alkenylene or C 3 -C 4 alkynylene;

each Q is independently phenyl, each optionally substituted with up to 2 substituents independently selected from R 12 ; or pyridinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl, oxazolyl, isoxazolyl, thienyl, isoxazolinyl, piperidinyl, morpholinyl or piperazinyl, each ring optionally substituted with up to 2 substituents independently selected from R 12 ;

each R 12 is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

each R 13 is independently H, halogen, methyl or methoxy;

each R 14 is independently H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl;

each R 17 is independently H, cyano, methyl or halomethyl;

n is 1, 2, or 3;

provided that:

(a) when R 1 is 1H-pyrazol-1-yl substituted with 1-2 substituents selected from CH 3 and J is unsubstituted phenyl, then L is other than CH 2 CH 2 , CH 2 CHF or CH(CH 3 );

(b) the compound of Formula 1 is not

wherein:

each R 1a may be the same or different;

m is 0; or

m is 1; R 1a is at the 3-position and is Cl or —CH(═O); or

m is 1; R 1a is at the 4-position and is halogen, cyano, —CH(═O), OHC(═O), C 2 -C 5 alkoxycarbonyl, NH 2 C(═O), CH 3 NHC(═O), CH 3 CH 2 NHC(═O), cyclopropyl-CH 2 NHC(═O), (CH 32 NC(═O), (CH 3 CH 2 ) 2 NC(═O), CH 3 ONHC(═O), CH 3 OCH 2 CH 2 NHC(═O), C≡CCH 2 NHC(═O), CH 3 ON(CH 3 )C(═O), CH 3 ON═CH CH 3 CH 2 ON═CH, CH 3 CH 2 CH 2 ON═CH, (CH 3 ) 2 CHON═CH or C≡CCH 2 ON═CH; or

m is 2; R 1a is at the 3- and 4-positions and is cyano, CF 2 H, CH 3 OCH 2 , C 2 -C 3 alkoxycarbonyl, cyclopropyl, phenyl or 4-chlorophenyl; or

m is 2; R 1a is at the 3- and 5-positions and is cyano, CH 3 , —CH(═O), CF 2 H, cyclopropyl, C 2 -C 3 alkoxycarbonyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl or 4-methoxyphenyl; or

m is 2; R 1a is at the 4- and 5-positions and is CF 2 H, cyclopropyl, CH 3 OCH 2 or C 2 -C 3 alkoxycarbonyl;

(c) the compound of Formula 1 is not

ethyl 1-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;

ethyl 1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;

ethyl 1-[2-fluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;

3-[4-[[(1-methyl-1H-pyrazol-3-yl)oxy]methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-[[(5-methyl-1H-pyrazol-3-yl)oxy]methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-[(2-fluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-[(2,6-difluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-(phenoxymethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-[(4-fluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;

3-[4-[(3,5-diethyl-1H-pyrazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole; and

3-[2-methoxy-4-(phenoxymethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

2. A compound of claim 1 wherein:

R 1 is U-1, U-2 or U-12;

L is (CR 4a R 4b ) n ;

J is J 63;

each R 2 is independently —C(═O)NR 3a R 3b , —C(R 6 )═NR 7 or —U—V-Q; or C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl or C 3 -C 6 alkynyloxycarbonyl, each optionally substituted with up to 1 substituent selected from R 10 ;

each R 3a is independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 3 -C 5 alkoxycarbonylalkyl;

each R 3b 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 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from C 2 -C 4 alkylcarbonyl and C 2 -C 4 alkoxycarbonyl;

each R 4a and R 4b is independently H or methyl;

each R 6 is independently H;

each R 7 is independently C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy or C 2 -C 4 alkynyloxy;

each R 10 is independently halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl or —C(R 13 )═NOR 14 ;

each V is independently a direct bond, C 1 -C 3 alkylene or C 2 -C 4 alkenylene;

each Q is independently phenyl, each optionally substituted with up to 2 substituents independently selected from R 12 ; or pyridinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl or oxazolyl, each ring optionally substituted with up to 2 substituents independently selected from R 12 ;

each R 12 is independently halogen, methyl or methoxy; and

each R 14 is independently H, methyl, halomethyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl.

3. A compound of claim 2 wherein:

R 1 is U-2 or U-12;

R 5a is H;

each R 2 is independently —C(═O)NR 3a R 3b ; or C 2 -C 6 alkoxycarbonyl, optionally substituted with up to 1 substituent selected from R 10 ;

each R 3a is independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkoxyalkyl or C 3 -C 5 alkoxycarbonylalkyl;

each R 3b is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 haloalkenyl, each optionally substituted with up to 1 substituent selected from C 2 -C 4 alkylcarbonyl and C 2 -C 4 alkoxycarbonyl; and

each R 10 is independently halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 2 -C 5 alkoxycarbonyl.

4. A compound of claim 3 wherein:

R 1 is U-2 connected at its 2-position to L; or

R 1 is U-12 connected at its 1-position to L;

each R 2 is independently —C(═O)NR 3a R 3b or C 2 -C 6 alkoxycarbonyl; and

n is 1.

5. A compound of claim 1 wherein:

R 1 is U-1, U-2, U-4, U-5 or U-12;

L is CH 2 , CH 2 CH 2 , OCH 2 or CH 2 O;

each R 5a is H;

each R 2 is independently —C(═O)NR 3a R 3b , —C(R 6 )═NR 7 or —U—V-Q; or C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl or C 3 -C 6 alkynyloxycarbonyl, each optionally substituted with up to 1 substituent selected from R 10 ;

each U is a direct bond;

each V is independently a direct bond, C 1 -C 3 alkylene or C 2 -C 4 alkenylene;

each Q is independently phenyl, each optionally substituted with up to 2 substituents independently selected from R 12 ; or pyridinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl or oxazolyl, each ring optionally substituted with up to 2 substituents independently selected from R 12 .

6. A compound of claim 5 wherein:

R 1 is U-2 or U-12;

x is 1 or 2;

L is CH 2 or CH 2 O;

each R 2 is independently —C(═O)NR 3a R 3b ; or C 2 -C 6 alkoxycarbonyl, optionally substituted with up to 1 substituent selected from R 10 ;

each R 3a is independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 3 -C 5 alkoxycarbonylalkyl;

each R 3b 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 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from C 2 -C 4 alkylcarbonyl and C 2 -C 4 alkoxycarbonyl; and

each R 10 is independently halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 2 -C 5 alkoxycarbonyl.

7. A compound of claim 6 wherein:

R 1 is U-2 connected at its 2-position to L; or

R 1 is U-12 connected at its 1-position to L; and

x is 1.

8. A compound of claim 1 that is:

wherein:

R 2 is ClCH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is F 2 CHCH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is N≡CCH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is MeOCH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is 1H-pyrazol-1-yl-CH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is CF 3 CH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is MeOCH 2 CH 2 NHC(═O); Z is S and L is CH 2 ; or

R 2 is FCH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is CF 3 OCH 2 CH 2 NHC(═O); Z is O and L is CH 2 ; or

R 2 is CF 3 CH 2 NHC(═O); Z is S and L is CH 2 ; or

R 2 is CF 3 CH 2 NHC(═O); Z is O and L is CH 2 .

9. A compound of claim 1 that is:

10. A compound of claim 1 that is:

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

12. 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.

13. 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 .

14. A method for controlling plant diseases caused by Basidiomycetes 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 .