Herbicidal pyrimidines

1. A compound selected from Formula I, an N-oxide or an agriculturally suitable salt thereof,

wherein

R 1 is phenyl optionally substituted with 1-3 R 7 ;

R 2 is ((O) j C(R 15 )(R 16 )) k R;

R is CO 2 H or a herbicidally effective derivative of CO 2 H;

R 3 is halogen, nitro, OR 20 , SR 21 or N(R 22 )R 23 ;

R 4 is —N(R 24 )R 25 or —NO 2 ;

each R 7 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenylthio, C 2 -C 4 haloalkenylthio, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 haloalkenylsulfonyl, C 3 -C 4 alkynylthio, C 3 -C 4 haloalkynylthio, C 3 -C 4 alkynylsulfinyl, C 3 -C 4 haloalkynylsulfinyl, C 3 -C 4 alkynylsulfonyl, C 3 -C 4 haloalkynylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 4 -C 6 (alkyl)cycloalkylamino, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl, phenyl, phenoxy and 5- or 6-membered heteroaromatic rings, each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R 45 ; or

two adjacent R 7 are taken together as —OCH 2 O—, —CH 2 CH 2 O—, —OCH(CH 3 )O—, —OC(CH 3 ) 2 O—, —OCF 2 O—, —CF 2 CF 2 O—, —OCF 2 CF 2 O—or —CH═CH—CH═CH—;

R 15 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, hydroxy, C 1 -C 4 alkoxy or C 2 -C 4 alkylcarbonyloxy;

R 16 is H, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or

R 15 and R 16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety;

R 20 is H, C 1 -C 4 alkyl or C 1 -C 3 haloalkyl;

R 21 is H, C 1 -C 4 alkyl or C 1 -C 3 haloalkyl;

R 22 and R 23 are independently H or C 1 -C 4 alkyl;

R 24 is H, C 1 -C 4 alkyl optionally substituted with 1-2 R 30 , C 2 -C 4 alkenyl optionally substituted with 1-2 R 31 , or C 2 -C 4 alkynyl optionally substituted with 1-2 R 32 ; or R 24 is C(═O)R 33 , nitro, OR34, S(O) 2 R 35 , N(R 36 )R 37 or N═C(R 62 )R 63 ;

R 25 is H, C 1 -C 4 alkyl optionally substituted with 1-2 R 30 or C(═O)R 33 ; or

R 24 and R 25 are taken together as a radical selected from —(CH 2 ) 4 —, —(CH 2 ) 5 —, —CH 2 CH═CHCH 2 — and —(CH 2 ) 2 O (CH 2 ) 2 —, each radical optionally substituted with 1-2 R 38 ; or

R 24 and R 25 are taken together as ═C(R 39 )N(R 40 )R 41 or ═C(R 42 )OR 43 ;

each R 30 , R 31 and R 32 is independently halogen, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino or C 2 -C 4 alkoxycarbonyl;

each R 33 is independently H, C 1 -C 14 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, phenyl, phenoxy or benzyloxy;

R 34 is H, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl or CHR 66 C(O)OR 67 ;

R 35 is C 1 -C 4 alkyl or C 1 -C 3 haloalkyl;

R 36 is H, C 1 -C 4 alkyl or C(═O)R 64 ;

R 37 is H or C 1 -C 4 alkyl;

each R 38 is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino or C 2 -C 4 alkoxycarbonyl;

R 39 is H or C 1 -C 4 alkyl;

R 40 and R 41 are independently H or C 1 -C 4 alkyl; or

R 40 and R 41 are taken together as —(CH 2 ) 4 —, —(CH 2 ) 5 —, —CH 2 CH═CHCH 2 —or —(CH 2 ) 2 O(CH 2 ) 2 —;

R 42 is H or C 1 -C 4 alkyl;

R 43 is C 1 -C 4 alkyl;

each R 45 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 4 -C 6 (alkyl)cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl;

R 62 is H, C 1 -C 4 alkyl or phenyl optionally substituted with 1-3 R 65 ;

R 63 is H or C 1 -C 4 alkyl; or

R 62 and R 63 are taken together as —(CH 2 ) 4 — or —(CH 2 ) 5 —;

R 64 is H, C 1 -C 14 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, phenyl, phenoxy or benzyloxy;

each R 65 is independently CH 3 , Cl or OCH 3 ;

R 66 is H, C 1 -C 4 alkyl or C 1 -C 4 alkoxy;

R 67 is H, C 1 -C 4 alkyl or benzyl;

j is 0 or 1; and

k is 0 or 1;

provided that:

(a) when k is 0, then j is 0;

(b) when R 1 is phenyl substituted by Cl in each of the meta positions, the phenyl is also substituted by R 7 in the para position;

(c) when R 1 is phenyl substituted by R 7 in the para position, said R 7 is other than tert-butyl, cyano or optionally substituted phenyl; and

(d) the compound of Formula I is other than diethyl 6-amino-5-nitro-2-phenyl-4-pyrimidinemalonate.

2. The compound of claim 1 wherein

R 2 is CO 2 R 12 , CH 2 OR 13 , CH(OR 46 )(OR 47 ), CHO, C(═NOR 14 )H, C(═NNR 48 R 49 )H, (O) j C(R 15 )(R 16 )CO 2 R 17 , C(═O)N(R 18 )R 19 , C(═S)OR 50 , C(═O)SR 51 , C(═S)SR 52 or C(═NR 53 )YR 54 ;

R 12 is H, —CH C(O)O(CH 2 ) m , —N═C(R 55 )R 56 ; or a radical selected from C 1 -C 14 alkyl, C 3 -C 12 cycloalkyl, C 4 -C 12 alkylcycloalkyl, C 4 -C 12 cycloalkylalkyl, C 2 -C 14 alkenyl, C 2 -C 14 alkynyl and phenyl, each radical optionally substituted with 1-3 R 27 ; or

R 12 is a divalent radical linking the carboxylic ester function CO 2 R 12 of each of two pyrimidine ring systems of Formula I, the divalent radical selected from —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 — and —CH(CH 3 )CH 2 —;

R 13 is H, C 1 -C 10 alkyl optionally substituted with 1-3 R 28 , or benzyl;

R 14 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or benzyl;

R 17 is C 1 -C 10 alkyl optionally substituted with 1-3 R 29 , or benzyl;

R 18 is H, C 1 -C 4 alkyl, hydroxy, C 1 -C 4 alkoxy or S(O) 2 R 57 ;

R 19 is H or C 1 -C 4 alkyl;

each R 27 is independently halogen, cyano, hydroxycarbonyl, C 2 -C 4 alkoxycarbonyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, —CH O(CH 2 ) n or phenyl optionally substituted with 1-3 R 44 ; or

two R 27 are taken together as —OC(O)O— or —O(C(R 58 )(R 58 )) 1-2 O—; or

two R 27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety;

each R 28 is independently halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 dialkylamino; or

two R 28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety;

each R 29 is independently halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 dialkylamino;

each R 44 is independently halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino or nitro;

R 46 and R 47 are independently C 1 -C 4 alkyl or C 1 -C 3 haloalkyl; or

R 46 and R 47 are taken together as —CH 2 CH 2 —, —CH 2 CH(CH 3 )— or —(CH 2 ) 3 —;

R 48 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or benzyl;

R 49 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 50 , R 51 and R 52 are H; or a radical selected from C 1 -C 14 alkyl, C 3 -C 12 cycloalkyl, C 4 -C 12 alkylcycloalkyl, C 4 -C 12 cycloalkylalkyl, C 2 -C 14 alkenyl and C 2 -C 14 alkynyl, each radical optionally substituted with 1-3 R 27 ;

Y is O, S or NR 61 ;

R 53 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkoxyalkyl, OH or C 1 -C 3 alkoxy;

R 54 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl; or

R 53 and R 54 are taken together as —(CH 2 ) 2 —, —CH 2 CH(CH 3 )—or —(CH 2 ) 3 —;

R 55 and R 56 are independently C 1 -C 4 alkyl;

R 57 is C 1 -C 4 alkyl, C 1 -C 3 haloalkyl or NR 59 R 60 ;

each R 58 is independently selected from H and C 1 -C 4 alkyl;

R 59 and R 60 are independently H or C 1 -C 4 alkyl;

R 61 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl;

m is an integer from 2 to 3; and

n is an integer from 1 to 4.

3. The compound of claim 2 wherein R 3 is halogen.

4. The compound of claim 2 wherein R 1 is phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions; and R 4 is —N(R 24 )R 25 .

5. The compound of claim 4 wherein R 2 is CO 2 R 12 , CH 2 OR 13 , CHO or CH 2 CO 2 R 17 .

6. The compound of claim 5 wherein R 24 is H, C(O)R 33 or C 1 -C 4 alkyl optionally substituted with R 30 ; R 25 is H or C 1 -C 2 alkyl; or R 24 and R 25 are taken together as ═C(R 39 )N(R 40 )R 41 .

7. The compound of claim 6 wherein R 2 is CO 2 R 12 ; and R 24 and R 25 are H.

8. The compound of claim 7 wherein R 12 is H, C 1 -C 4 alkyl or benzyl.

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

methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid,

ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate,

methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, and

6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid.

10. A herbicidal mixture comprising a herbicidally effective amount of a compound of claim 1 and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

11. A herbicidal mixture comprising synergistically effective amounts of a compound of claim 1 and an auxin transport inhibitor.

12. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent.

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 herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 , an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent.

15. The compound of claim 1 selected from the group consisting of:

methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid,

ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate,

methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, and

6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid.

16. The compound of claim 15 selected from the group consisting of:

methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid,

ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate,

6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid, and

methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate.

17. A compound of claim 1 which is methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate.

18. A compound of claim 1 which is ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate.

19. A compound of claim 1 which is 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid.

20. A herbicidal mixture comprising a herbicidally effective amount of a compound of claim 15 , and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

21. The herbicidal mixture of claim 10 wherein the additional active ingredient is selected from the group consisting of:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron.

22. The herbicidal mixture of claim 21 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of:

chlorsulfuron and flucarbazone-sodium;

chlorsulfuron and sulfometuron-methyl;

flumetsulam, nicosulfuron and rimsulfuron;

mesosulfuron-methyl and iodosulfuron-methyl;

metsulfuron-methyl and chlorsulfuron;

metsulfuron-methyl and sulfometuron-methyl;

metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl;

imazapyr and metsulfuron-methyl;

imazapyr, metsulfuron-methyl and sulfometuron-methyl;

imazapyr and sulfometuron-methyl;

rimsulfuron and nicosulfuron;

rimsulfuron and thifensulfuron-methyl;

thifensulfuron-methyl and metsulfuron-methyl;

tribenuron-methyl and metsulfuron-methyl;

tribenuron-methyl and thifensulfuron-methyl;

bensulfuron-methyl and metsulfuron-methyl; and

metsulfuron-methyl and chlorimuron-ethyl.

23. The herbicidal mixture of claim 20 wherein the additional active ingredient is selected from the group consisting of:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron.

24. The herbicidal mixture of claim 23 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of:

chlorsulfuron and flucarbazone-sodium;

chlorsulfuron and sulfometuron-methyl;

flumetsulam, nicosulfuron and rimsulfuron;

mesosulfuron-methyl and iodosulfuron-methyl;

metsulfuron-methyl and chlorsulfuron;

metsulfuron-methyl and sulfometuron-methyl;

metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl;

imazapyr and metsulfuron-methyl;

imazapyr, metsulfuron-methyl and sulfometuron-methyl;

imazapyr and sulfometuron-methyl;

rimsulfuron and nicosulfuron;

rimsulfuron and thifensulfuron-methyl;

thifensulfuron-methyl and metsulfuron-methyl;

tribenuron-methyl and metsulfuron-methyl;

tribenuron-methyl and thifensulfuron-methyl;

bensulfuron-methyl and metsulfuron-methyl; and

metsulfuron-methyl and chlorimuron-ethyl.

25. A herbicidal mixture comprising synergistically effective amounts of a compound of claim 15 and an auxin transport inhibitor.

26. The herbicidal mixture of claim 11 wherein the compound is selected from the group consisting of :

methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid,

ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate,

6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid, and

methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate

and the auxin transport inhibitor is diflufenzopyr.

27. The herbicidal mixture of claim 11 wherein the compound is ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate and the auxin transport inhibitor is diflufenzopyr.

28. The herbicidal mixture of claim 20 further comprising at least one of a surfactant, a solid diluent or a liquid diluent.

29. The herbicidal mixture of claim 25 further comprising at least one of a surfactant, a solid diluent or a liquid diluent.

30. The herbicidal mixture of claim 28 wherein the additional active ingredient is selected from the group consisting of:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron.

31. The herbicidal mixture of claim 30 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of:

chlorsulfuron and flucarbazone-sodium;

chlorsulfuron and sulfometuron-methyl;

flumetsulam, nicosulfuron and rimsulfuron;

mesosulfuron-methyl and iodosulfuron-methyl;

metsulfuron-methyl and chlorsulfuron;

metsulfuron-methyl and sulfometuron-methyl;

metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl;

imazapyr and metsulfuron-methyl;

imazapyr, metsulfuron-methyl and sulfometuron-methyl;

imazapyr and sulfometuron-methyl;

rimsulfuron and nicosulfuron;

rimsulfuron and thifensulfuron-methyl;

thifensulfuron-methyl and metsulfuron-methyl;

tribenuron-methyl and metsulfuron-methyl;

tribenuron-methyl and thifensulfuron-methyl;

bensulfuron-methyl and metsulfuron-methyl; and

metsulfuron-methyl and chlorimuron-ethyl.

32. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 23 .

33. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 24 .

34. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 25 .

35. A herbicidal mixture comprising a herbicidally effective amount of a compound of claim 16 , and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

36. A herbicidal mixture comprising synergistically effective amounts of a compound of claim 16 and an auxin transport inhibitor.

37. A compound of claim 1 wherein each R 7 is independently selected from halogen, C 1 -C 2 alkyl, C 1 fluoroalkyl, C 1 -C 2 alkoxy or C 1 fluoroalkoxy.

38. A compound of claim 1 wherein each R 7 is independently selected from halogen, methyl and methoxy.