Pyrimidinyloxy benzo-fused compounds as herbicides

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

wherein

K together with the two contiguous linking carbon atoms forms a 4-, 5- or 6-membered ring selected from the group consisting of K-1, K-2, K-3, K-4, K-5, K-6, K-7, K-8, K-9, K-10, K-11, K-12, K-13, K-14, K-15, K-16 and K-17:

R is C 2 -C 5 haloalkyl;

each R 1a is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano or S(O) p R 8 ;

each R 1b is independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano and S(O) p R 8 ;

each R 1c is independently selected from hydrogen, F, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano and S(O) p R 8 ;

R 2 is halogen, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or S(O) q R 9 ;

each R 3 is independently halogen, cyano, nitro, 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 or C 2 -C 4 alkylthioalkyl;

m is 0, 1, 2 or 3;

each n is independently selected from 0 and 1;

p is 0, 1 or 2;

q is 0, 1 or 2;

r is 0, 1 or 2;

Z is O or S;

R 4 is nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or S(O) r R 9 ;

R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 6 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl or C 2 -C 6 cyanoalkyl;

each R 7a and R 7b is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 8 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; and

R 9 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylamino or C 2 -C 10 dialkylamino.

2. The compound of claim 1 wherein

K is K-2, K-3, K-4, K-5, K-6, K-7, K-10, K-11, K-12, K-13, K-14 or K-15;

Z is O;

R 1a is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or cyano;

each R 1b is independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and cyano;

each R 1c is independently selected from hydrogen, F, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and cyano;

R 2 is halogen, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl or C 3 -C 6 cycloalkyl;

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

m is 0 or 1.

3. The compound of claim 2 wherein

K is K-2, K-3, K-4, K-5, K-6, K-7, K-8 or K-10;

R 1a is hydrogen, halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, hydroxy or cyano;

each R 1b is independently selected from halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, hydroxy and cyano;

each R 1c is independently selected from hydrogen, F, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, hydroxy and cyano;

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

R 3 is at the 5- or 6-position and selected from halogen or cyano.

4. The compound of claim 3 wherein

K is K-2, K-3, K-4, K-5, K-6, K-7 or K-8.

5. The compound of claim 4 wherein K is K-3, K-5 or K-7;

R is C 3 -C 4 haloalkyl;

R 1a is H, F, OH, CF 3 or CN;

R 1b is independently selected from F, OH, CF 3 and CN;

R 1c is independently selected from H, F, OH, CF 3 and CN;

R 2 is halogen; and

R 3 is F or cyano.

6. The compound of claim 5 wherein

R is —CH 2 CH 2 CF 3 or —CH 2 CH 2 CH 2 CF 3 ;

R 1a is hydrogen;

each R 1c is hydrogen;

R 2 is Cl; and

each n is 0.

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

4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(4,4,4-trifluorobutyl)-1(3H)-isobenzofuranone;

(3S)-4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(4,4,4-trifluorobutyl)-1-(3H)-isobenzofuranone;

(3R)-4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(4,4,4-trifluorobutyl)-1-(3H)-isobenzofuranone;

4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(3,3,3-trifluoropropyl)-1(3H)-isobenzofuranone;

8-[(5-Chloro-2-pyrimidinyl)oxy]-1-(4,4,4-trifluorobutyl)-1H-2-benzopyran-4(3H)-one;

4-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-3-(4,4,4-trifluorobutyl)-1H-inden-1-one;

5-Chloro-2-[[1,3-dihydro-3-(4,4,4-trifluorobutyl)-4-isobenzofuranyl]oxy]pyrimidine;

5-Chloro-2-[[1,3-dihydro-3-(3,3,3-trifluoropropyl)-4-isobenzofuranyl]oxy]pyrimidine;

5-Chloro-2-[[2,3-dihydro-3-(4,4,4-trifluorobutyl)-1H-inden-4-yl]oxy]pyrimidine;

4-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-3-(4,4,4-trifluorobutyl)-1H-inden-1-ol;

4-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-3-(3,3,3-trifluoropropyl)-1H-inden-1-one;

4-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-2-methyl-3-(4,4,4-trifluorobutyl)-1H-isoindol-1-one;

4-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-3-(4,4,4-trifluorobutyl)-1H-isoindol-1-one;

7-[(5-Chloro-2-pyrimidinyl)oxy]-2,3-dihydro-1-(3,3,3-trifluoropropyl)-1H-inden-1-ol;

5-Chloro-2-[[1-oxido-3-(4,4,4-trifluorobutyl)-3H-2,1-benzoxathiol-4-yl]oxy]pyrimidine;

5-[(5-Chloro-2-pyrimidinyl)oxy]-3,4-dihydro-4-(4,4,4,-trifluorobutyl)-1H-2benzopyran-1-one;

8-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-1-(4,4,4-trifluorobutyl)-3H-2-benzopyran-3-one;

(3S)-4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(3,3,3-trifluoropropyl)-1(3H)-isobenzofuranone;

(3R)-4-[(5-Chloro-2-pyrimidinyl)oxy]-3-(3,3,3-trifluoropropyl)-1(3H)-isobenzofuranone;

5-Chloro-2-[[(3R)-1,3-dihydro-3-(3,3,3-trifluoropropyl)-4-isobenzofuranyl]oxy]-pyrimidine;

5-Chloro-2-[[(3S)-1,3-dihydro-3-(3,3,3-trifluoropropyl)-4-isobenzofuranyl]oxy]-pyrimidine;

2-[(5-Chloro-2-pyrimidinyl)oxy]-8-(4,4,4-trifluorobutyl)bicyclo[4.2.0]octa-1,3,5-trien-7-one;

5-[(5-Chloro-2-pyrimidinyl)oxy]-3,4-dihydro-3-(3,3,3-trifluoropropyl)-1H-2-benzopyran-1-one;

2-[(5-Chloro-2-pyrimidinyl)oxy]-8-(3,3,3-trifluoropropyl)bicyclo[4.2.0]octa-1,3,5-trien-7-one;

5-[(5-Chloro-2-pyrimidinyl)oxy]-3,4-dihydro-4-(3,3,3-trifluoropropyl)-1H-2-benzopyran-1-one;

5-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-4-(4,4,4-trifluorobutyl)-3H-2-benzopyran-3-one;

5-Chloro-2-[[3,4-dihydro-1-(4,4,4-trifluorobutyl)-1H-2-benzopyran-8-yl]oxy]pyrimidine;

8-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-1-(3,3,3-trifluoropropyl)-3H-2-benzopyran-3-one;

5-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-4-(3,3,3-trifluoropropyl)-3H-2-benzopyran-3-one;

5-[(5-Chloro-2-pyrimidinyl)oxy]-3,4-dihydro-4-(4,4,4-trifluorobutyl)-1(2H)-naphthalenone;

5-[(5-Chloro-2-pyrimidinyl)oxy]-3,4-dihydro-3-(5,5,5-trifluoropentyl)-1H-2-benzopyran-1-one;

5-Chloro-2-[[3,4-dihydro-1-(3,3,3-trifluoropropyl)-1H-2-benzopyran-8-yl]oxy]pyrimidine;

5-Chloro-2-[[2,3-dihydro-3-(4,4,4-trifluorobutyl)-4-benzofuranyl]oxy]pyrimidine;

5-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-4-(5,5,5-trifluoropentyl)-3H-2-benzopyran-3-one;

8-[(5-Chloro-2-pyrimidinyl)oxy]-1,4-dihydro-1-propyl-3H-2-benzopyran-3-one; and

5-Chloro-2-[[2,3-dihydro-3-(3,3,3-trifluoropropyl)-4-benzofuranyl]oxy]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 (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).

11. A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient selected from (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.

12. 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, nicosulfuron, pyrasulfotole, pyroxasulfone, pyroxsulam, rimsulfuron, saflufenacil, tembotrione, thifensulfuron-methyl, topramazone and tribenuron.

13. 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 .

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

wherein

K together with the two contiguous linking carbon atoms forms a 4-, 5- or 6-membered ring selected from the group consisting of K-1, K-2, K-3, K-4, K-5, K-6, K-7, K-8, K-9, K-10, K-11, K-12, K-13, K-14, K-15, K-16 and K-17:

R is C 1 -C 6 alkyl, C 2 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 halocycloalkylalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 10 dialkylamino, C 2 -C 10 halodialkylamino, C 3 -C 6 cycloamino, 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 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 4 -C 8 halocycloalkylalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkoxyhaloalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 3 -C 7 cyanoalkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 nitroalkyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkenylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 haloalkylthioalkyl, benzyl, —N(R 5 )(OR 6 ), —ON(R 7a )(R 7b ) or —N(R 5 )N(R 7a )(R 7b );

each R 1a is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, alkoxy, C 1 -C 4 haloalkoxy, cyano or S(O) R 8 ;

each R 1b is independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano and S(O) p R 8 ;

each R 1c is independently selected from hydrogen, F, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano and S(O) p R 8 ;

R 2 is halogen, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or S(O) q R 1 ;

each R 3 is independently halogen, cyano, nitro, 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, 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, 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 or C 2 -C 4 alkylthioalkyl;

m is 0, 1, 2 or 3;

each n is independently selected from 0 and 1;

p is 0, 1 or 2;

q is 0, 1 or 2;

r is 0, 1 or 2;

Z is O or S;

R 4 is nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or S(O) r R 9 ;

R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 6 is H, alkyl, haloalkyl, C 2 alkoxyalkyl, C 2 haloalkoxyalkyl or C 2 -C 6 cyanoalkyl;

each R 7a and R 7b is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 8 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; and

R 9 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylamino or C 2 -C 10 dialkylamino.