Herbicidal substituted pyrimidinyloxy benzene compounds

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

wherein

each Y 1 , Y 2 , Y 3 and Y 4 is independently selected from the group consisting of N and CR 1 , provided no more than 3 of Y 1 , Y 2 , Y 3 and Y 4 are N;

Z is selected from the group consisting of O and S;

each R 1 is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, SF 5 , 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 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, 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 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, SO n R 1A , Si(CH 3 ) 3 , B(—OC(R 1B ) 2 C(R 1B ) 2 O—); a phenyl ring optionally substituted with up to 5 substituents independently selected from R 1C ; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 1C on carbon atom ring members and R 1D on nitrogen atom ring members;

R 2 is selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, SO n R 2A , C 1 -C 4 haloalkyl and C 3 -C 6 cycloalkyl;

m is selected from the group consisting of 0, 1, 2 and 3;

each R 3 is independently selected from the group consisting of halogen, cyano, hydroxy, nitro, amino, 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 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 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, Si(CH 3 ) 3 , C≡CSi(CH 3 ) 3 , C(═O)N(R 3A )(R 3B ), C(═NOR 3C )H, C(═NR 3D )H, SO n R 3E ; a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 3F on carbon atom ring members and R 3G on nitrogen atom ring members; and pyrimidinyloxy;

each n is independently selected from the group consisting of 0, 1 and 2;

each R 1A , R 2A and R 3E is independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylamino and C 2 -C 6 dialkylamino;

each R 1B is independently selected from the group consisting of H and C 1 -C 4 alkyl;

each R 1C is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy;

each R 1D is independently selected from the group consisting of cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 2 -C 6 alkylcarbonyl;

each R 3A is independently selected from the group consisting of C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;

each R 3B is independently selected from the group consisting of H, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;

each R 3C is independently selected from the group consisting of H and C 1 -C 4 alkyl;

each R 3D is independently selected from the group consisting of H, amino, C 1 -C 4 alkyl and C 1 -C 4 alkylamino;

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

each R 3G is independently selected from the group consisting of cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 2 -C 6 alkylcarbonyl;

provided when i) Y 1 is N; Y 2 is CH; Y 3 is CBr; Y 4 is CH; and R 2 is Cl, then R 3 is other than 5-CF 3 , 5-CN or 5-NO 2 ; ii) Y 1 is N; Y 2 is CH; Y 3 is CBr; Y 4 is CH; and R 2 is Br, then R 3 is other than 5-CF 3 ; and iii) Y 1 is N; Y 2 is CCH 3 ; Y 3 is CCl; Y 4 is CCl; and R 2 is Cl, then m is other than 0.

2. A compound of claim 1 wherein

—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached is selected from the group consisting of

Z is O;

each R 1 is independently selected from the group consisting of hydrogen, halogen, cyano, SF 5 , 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 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 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 cyanoalkyl, C 2 -C 4 alkylthioalkyl, SO n R 1A , Si(CH 3 ) 3 and B(—OC(R 1B ) 2 C(R 1B ) 2 O—);

R 2 is 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, 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 8 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 3A )(R 3B ), C(═NOR 3C )H, SO n R 3E ; a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 3F on carbon atom ring members and R 3G on nitrogen atom ring members; and

m is selected from the group consisting of 0, 1 and 2.

3. A compound of claim 2 wherein

—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached is selected from the group consisting of Q-2 and Q-5;

each R 1 is independently selected from the group consisting of hydrogen, 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 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 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 4 alkylthioalkyl and SO n R 1A ;

R 2 is selected from the group consisting of halogen and C 1 -C 4 alkyl;

each R 3 is independently selected from the group consisting of 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 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 cyanoalkyl, SO n R 3E ; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 3F on carbon atom ring members and R 3G on nitrogen atom ring members; and

m is selected from the group consisting of 0 and 1.

4. A compound of claim 3 wherein

each R 1 is independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and SO n R 1A ;

R 2 is selected from the group consisting of halogen and CH 3 ;

each R 3 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxyalkyl and C 2 -C 6 haloalkoxyalkyl; and

each R 1A is independently selected from the group consisting of C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

5. A compound of claim 4 wherein

—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached is Q-2;

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

each R 3 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

6. A compound of claim 4 wherein

—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached is Q-5;

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

each R 3 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

7. A compound of claim 1 selected from the group consisting of

5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine,

5-bromo-2-[2-(4-chloro-1H-pyrazol-1-yl)phenoxy]pyrimidine,

2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine,

2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-fluoropyrimidine,

5-bromo-2-[2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine,

2-(4-bromo-1H-pyrazol-1-yl)-3-[(5-chloro-2-pyrimidinyl)oxy]benzonitrile,

2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine,

3[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,

3-[(5-bromo-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,

5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine,

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

5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]phenoxy]pyrimidine,

3-[(5-fluoro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,

2-[2-(4-bromo-1H-pyrazol-1-yl)-3-fluorophenoxy]-5-chloropyrimidine,

3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]benzonitrile,

5-chloro-2-[2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]phenoxy]pyrimidine,

2-[2-(4-bromo-1H-pyrazol-1-yl)-3-(difluoromethyl)phenoxy]-5-chloropyrimidine,

3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(difluoromethyl)-1H-pyrazol-1-yl]benzonitrile,

3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]benzonitrile,

5-bromo-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine and

5-chloro-2-[3-fluoro-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine.

8. 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.

9. 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.

10. 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 solanesyl transferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides 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 of compounds of (b1) through (b16).

11. 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 .

12. A method for controlling the growth of undesired vegetation in a 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 or mesotrione tolerance, comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1 .

13. 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, (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.

14. A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient 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, nicosulfuon, pyrasulfotole, pyroxasulfone, pyroxsulam, rimsulfuron, saflufenacil, tembotrione, thifensulfuron-methyl, topramazone and tribenuron.