HERBICIDAL PYRIMIDINYLMETHYL-SUBSTITUTED 1,2,4-TRIAZOLES

1 . A compound of Formula 1, stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

R 1 is halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 7 cycloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 1 -C 4 haloalkoxy or C 2 -C 7 alkoxyalkyl;

R 2 is cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 7 alkoxyalkoxy, C 3 -C 7 cycloalkyl, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl;

Q is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 2 -C 5 haloalkylcarbonyl, C 2 -C 5 haloalkoxycarbonyl or C 1 -C 4 alkoxyalkyl; or G;

G is phenyl, or a 5- or 6-membered heterocyclic ring; the phenyl or heterocyclic ring unsubstituted or substituted with 1 or 2 R 3 ; and

R 3 is halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 5 cycloalkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl.

2 . The compound of claim 1 wherein

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

R 2 is cyano, nitro, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

Q is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 2 -C 5 haloalkylcarbonyl, C 2 -C 5 haloalkoxycarbonyl; or G;

G is phenyl substituted with 1 or 2 R 3 ; or a 5- or 6-membered heterocyclic ring substituted with 1 or 2R 3 ; and

R 3 is halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio.

3 . The compound of claim 2 wherein

R 1 is F, Cl, Br, nitro or CH 3 ;

R 2 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

Q is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl or C 2 -C 5 haloalkylcarbonyl; or G;

G is selected from

R 3 is R 3a , R 3b , R 3c , R 3d or R 3e ; and

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

4 . The compound of claim 3 wherein

R 1 is F, Cl, Br, nitro or CH 3 ;

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

Q is C 1 -C 6 alkyl, C 3 -C 6 haloalkyl, C 3 -C 6 haloalkylthio, C 3 -C 6 haloalkoxy, C 3 -C 5 alkylcarbonyl, C 3 -C 5 alkoxycarbonyl or C 3 -C 5 haloalkylcarbonyl; or G;

G is selected from G-1, G-2, G-6, G-7, G-8 and G-15;

R 3a is Cl, F or CF 3 ;

R 3b is Cl or F; and

R 3d is Cl, CHF 2 or CF 3 .

5 . The compound of claim 4 wherein

R 1 is Cl, Br, nitro or CH 3 ;

R 2 is C 1 -C 2 haloalkyl;

Q is C 1 -C 6 alkyl or C 3 -C 6 haloalkyl; or G;

G is G-1, G-2, G-6 and G-7; and

R 3a is Cl or CF 3 .

6 . The compound of claim 5 wherein

R 1 is Cl or Br;

R 2 is CHF 2 , CF 3 or CF 2 Cl;

Q is —CH 2 CF 3 , —CH 2 CH 2 CF 3 —CH 2 CH 2 CH 2 CF 3 or —OCH 2 CH 2 CH 2 CF 3 ; or G;

G is G-1 and G-2.

7 . The compound of claim 5 wherein

G is G-2;

R 3a is F; and

R 3b is Cl.

8 . The compound of claim 5 wherein

G is G-2;

R 3a is F; and

R 3b is Cl.

9 . A compound of claim 1 that is

5-chloro-2-[[3-(trifluoromethyl)-5-[4-(trifluoromethyl)phenyl]-1H-1,2,4-triazol-1-yl]methyl]pyrimidine.

10 . A compound of Formula 6a

wherein

R 1 is halogen;

R 2 is C 1 -C 4 haloalkyl; and

X is Br, Cl or I.

11 . The compound of claim 10 wherein

R 1 is Cl;

R 2 is C 1 -C 2 haloalkyl; and

X is Br or I.

12 . The compound of claim 11 wherein

R 2 is CF 3 ; and

X is Br or I.

13 . A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

14 . The herbicidal composition of claim 13 and at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

15 . A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient selected (b) at least one additional active ingredient selected from photosystem II inhibitors (b1), AHAS inhibitors (b2), ACCase inhibitors (b3), auxin mimics (b4), EPSP synthase inhibitors (b5), photosystem I electron diverters (b6), PPO inhibitors (b7), GS inhibitors (b8), VLCFA elongase inhibitors (b9), auxin transport inhibitors (b10), PDS inhibitors (b11), HPPD inhibitors (b12), DXP synthase inhibitors (b13), HST inhibitors (b14), cellulose biosynthesis inhibitors (b15), DHODH inhibitors (b16), other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinflubrolin, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb (b17), and herbicide safeners (b18); and salts of compounds of (b1) through (b18).

16 . The herbicidal mixture of claim 15 wherein the at least one additional active ingredient is selected from DXP synthase inhibitors (b13), HST inhibitors (b14), cellulose biosynthesis inhibitors (b15), and DHODH inhibitors (b16); and salts thereof.

17 . A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1 .

18 . The method of claim 17 for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a composition of a compound of claim 1 and at least one additional herbicide or herbicide safener.