Pyrimidinyloxy benzene derivatives as herbicides

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

wherein

A is

B is O or S;

R 1 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 3 -C 6 cycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio or C 1 -C 6 alkenylthio;

Z is O;

R 2 is halogen;

each R 3 is independently halogen, cyano, CHO, C(═O)NH 2 , C(═S)NH 2 , SO 2 NH 2 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 7 cycloalkylcarbonyl, C 2 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkoxyhaloalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 2 -C 4 alkylthioalkyl, —C(═O)N(R 11a )(R 11b ), —C(═NOR 12 )H, —C(═N(R 13 ))H or —SO—R 14 ;

m is 0, 1, 2 or 3;

each n is independently 0, 1 or 2;

each R 11a is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 11b is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 12 is independently H or C 1 -C 4 alkyl;

each R 13 is independently H, amino, C 1 -C 4 alkyl or C 1 -C 4 alkylamino; and

each R 14 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylamino or C 2 -C 10 dialkylamino;

provided that the compound of Formula 1 is other than methyl 2-[(5-chloro-2-pyrimidinyl)oxy]benzoate, methyl 2-[(5-bromo-2-pyrimidinyl)oxy]benzoate and 1-[2-[(5-bromo-2-pyrimidinyl)oxy]phenyl]-ethanone.

2. The compound of claim 1 wherein

R 1 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;

R 2 is F, Cl or Br;

each R 3 is independently halogen, cyano, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and

m is 1 or 2.

3. The compound of claim 2 wherein

B is O;

R 1 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio or C 1 -C 6 alkenylthio;

R 2 is Cl;

each R 3 is independently halogen, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; and

m is 1 or 2.

4. The compound of claim 2 wherein

B is O;

R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;

R 2 is F, Cl or Br;

each R 3 is independently halogen, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; and

m is 1 or 2.

5. The compound of claim 2 wherein

B is O;

R 1 is C 1 -C 6 haloalkyl;

R 2 is Cl;

each R 3 is independently halogen, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; and

m is 1 or 2.

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

3,3,3-trifluoropropyl 2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

3,3,3-trifluoro-1-methylpropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

propyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

4,4,4-trifluorobutyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

2-propen-1-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

3-buten-1-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

2,2,3,3,3-pentafluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate;

3,3,3-trifluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate; and

1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone.

7. The compound of claim 1 wherein

R 1 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 3 -C 6 cycloalkoxy, C 4 -C 5 cycloalkylalkoxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio or C 1 -C 6 alkenylthio;

R 2 is halogen;

each R 3 is independently halogen, cyano, CHO, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 6 alkylcycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 cyanoalkyl, —C(═O)N(R 11a R 11b ), —C(═NOR 12 )H or —SO n R 14 ;

R 11a is C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

R 11b is C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

R 12 is H or C 1 -C 3 alkyl; and

R 14 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl.

8. The compound of claim 1 that is 1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone.

9. 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.

10. 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.

11. The herbicidal composition of claim 10 wherein the at least one additional active ingredient is 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 solanesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).

12. The herbicidal composition of claim 10 wherein the at least one additional active ingredient is selected from the group consisting of (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors and (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors.

13. The herbicidal composition of claim 10 wherein the at least one additional active ingredient is selected from the group consisting of 2,4-D, acetochlor, alachlor, atrazine, bromoxynil, bentazon, bicyclopyrone, carfentrazone-ethyl, cloransulam-methyl, dicamba, dimethenamid-p, florasulam, flufenacet, flumioxazin, flupyrsulfuron-methyl, fluroxypyr-meptyl, glyphosate, halauxifen-methyl, isoxaflutole, MCPA, mesotrione, metolachlor, metsulfuron-methyl, nicosulfuron, pyrasulfotole, pyroxasulfone, pyroxsulam, rimsulfuron, saflufenacil, tembotrione, thifensulfuron-methyl, topramazone and tribenuron.

14. The herbicidal composition of claim 10 wherein the at least one additional active ingredient comprises glyphosate.

15. 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 .

16. A method for controlling the growth of undesired vegetation in genetically modified plants that exhibit traits of glyphosate tolerance, glufosinate tolerance, ALS herbicide tolerance, dicamba tolerance, imidazolinone herbicide tolerance, 2,4-D tolerance, HPPD tolerance and mesotrione tolerance, comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1 .