Pyrimidinyloxy benzene derivatives as herbicides

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

Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, and is selected from the group consisting of

wherein r is 0, 1, 2 or 3;

Z is O or S;

each R 1 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkoxy;

R 2 is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 3 -C 6 cycloalkyl;

each R 3 is independently selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkoxy;

m is 0, 1, 2 or 3;

each n is independently 0, 1 or 2.

2. The compound of claim 1 wherein

Q is selected from the group consisting of Q-12, Q-16, Q-18, Q-43, Q-44, Q-45 and Q-49

wherein r is 0 or 1

R 1 is independently selected from the group consisting of halogen, C 1 -C 4 alkyl, and C 1 -C 4 haloalkyl,

each R 3 is independently selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkoxy;

Z is O; and

m is 0, 1 or 2.

3. The compound of claim 2 wherein

R 1 is independently halogen or C 1 -C 4 haloalkyl;

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

R 3 is independently selected from the group consisting of halogen, C 1 -C 4 alkyl, and C 1 -C 4 haloalkoxy; and

m is 0 or 1.

4. The compound of claim 3 wherein

Q is selected from the group consisting of Q-12, Q-16 and Q-18.

5. The compound of claim 4 wherein

Q is Q-16 or Q-18;

R 1 is C 1 -C 4 haloalkyl;

R 2 is halogen;

R 3 is halogen;

r is 1; and

m is 1.

6. The compound of claim 1 wherein

Q is selected from Q-43, Q-44, Q-45and Q-49; and

Z is O.

7. The compound of claim 6 wherein

each R 1 is independently selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy;

R 2 is halogen; and

each R 3 is independently halogen or C 1 -C 4 alkyl.

8. The compound of claim 1 selected from the group consisting of

5-chloro-2-[2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine,

5-chloro-2-[2-[5-(fluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine,

2-[2-(3-bromo-5-isoxazolyl)phenoxy]-5-chloropyrimidine,

5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine,

5-chloro-2-[3-chloro-2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine,

4-[2-[(5-bromo-2-pyrimidinyl)oxy]phenyl]-2-(trifluoromethyl)pyrimidine,

2-[2-(2-bromo-5-thiazolyl)phenoxy]-5-(trifluoromethyl)pyrimidine, and

5-chloro-2 -[4-methyl-2-[2-(trifluoromethyl)-4-pyridinyl]phenoxy]pyrimidine.

9. The compound of claim 1 selected from the group consisting of

5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine,

5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine,

5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine,

5-bromo-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine,

5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine,

5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,

5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,

5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine

5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine,

5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3-difluoromethoxyphenoxy]pyrimidine,

5-chloro-2-[2-[5-(cyclopropyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine,

5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,

5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3-bromophenoxy]pyrimidine,

5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-bromo-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,

5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-bromophenoxy]pyrimidine and

5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3-bromophenoxy]pyrimidine.

10. The compound of claim 1 which is 5-chloro-2-[2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine.

11. The compound of claim 1 which is 5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine.

12. The compound of claim 1 which is 5-chloro-2-[2-[5-(cyclopropyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine.

13. The compound of claim 1 which is 5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine.

14. The compound of claim 1 which is 5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3-bromophenoxy]pyrimidine.

15. The compound of claim 1 which is 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine.

16. The compound of claim 1 which is 5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine.

17. 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.

18. A herbicidal composition comprising a compound of claim 1 , 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.

19. A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient selected from the group consisting of (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) herbicide selected from the group consisting of mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts thereof.

20. 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 .