IP Library Granted Patent US 7,863,220
Granted Patent B2
US 7,863,220 · App. 10/581,897 · Granted Jan 4, 2011

Herbicidal pyrimidines

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,863,220
App. No.
10/581,897
Granted
Jan 4, 2011
Kind
B2
Abstract

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein R 1 is cyclopropyl optionally substituted with 1-5 R 5 , isopropyl optionally substituted with 1-5 R 6 , or 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, cyano, nitro, OR 20 , SR 21 or N(R 22 )R 23 ; R 4 is —N(R 24 )R 25 or —NO 2 ; j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0; and R 5 , R 6 , R 7 , R 15 , R 16 , R 20 , R 21 , R 22 , R 23 , R 24 and R 25 are as defined in the disclosure. Also disclosed are compositions comprising the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I. Also disclosed are compositions comprising a compound of Formula I and at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

Claims (190)

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

wherein

R 1 is cyclopropyl optionally substituted with 1-5 R 5 or isopropyl optionally substituted with 1-5 R 6 ;

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, OR 20 , SR 21 or N(R 22 )R 23 ;

R 4 is —N(R 24 )R 25 or —NO 2 ;

each R 5 and R 6 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 2 haloalkylthio;

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, OR 34 , 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 1-4 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;

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 1-4 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; and

(b) when R 1 is cyclopropyl or isopropyl optionally substituted with 1-5 R 6 , then R is other than C(═W)N(R b )S(O) 2 —R c —R d wherein W is O, S, NR e or NOR e ; R b is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; R c is a direct bond or CHR f , O, NR e or NOR e ; R d is an optionally substituted heterocyclic or carbocyclic aromatic radical having 5 to 6 ring atoms, the radical being optionally condensed with an aromatic or nonaromatic 5- or 6-membered ring; each R e is independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or phenyl; and R f is H, C 1 -C 3 alkyl or phenyl.

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, —CHC(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, —CHO(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 cyclopropyl; 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-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt,

methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

phenylmethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt and

ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate.

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. A compound which is 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid.

16. A compound which is 5-chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidine-carboxylic acid.

17. A compound which is 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid.

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

methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate,

6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt,

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid,

methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

phenylmethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt,

6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid and

ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate.

19. The compound of claim 18 selected from the group consisting of:

ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate and

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid.

20. A compound of claim 1 which is 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid.

21. A compound of claim 1 which is methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate.

22. A compound of claim 1 which is 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid.

23. A compound of claim 1 which is ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate.

24. A compound of claim 1 which is methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate.

25. A compound of claim 1 which is ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate.

26. A herbicidal mixture comprising a herbicidally effective amount of a compound of claim 18 or 19 , and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

27. 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.

28. The herbicidal mixture of claim 27 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.

29. The herbicidal mixture of claim 26 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.

30. The herbicidal mixture of claim 29 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.

31. A herbicidal mixture comprising synergistically effective amounts of a compound of either of claim 18 or 19 and an auxin transport inhibitor.

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

ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate,

methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate and

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid, and the auxin transport inhibitor is diflufenzopyr.

33. 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.

34. The herbicidal mixture of claim 26 further comprising at least one of a surfactant, a solid diluent or a liquid diluent.

35. The herbicidal mixture of claim 31 further comprising at least one of a surfactant, a solid diluent or a liquid diluent.

36. The herbicidal mixture of claim 34 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.

37. The herbicidal mixture of claim 36 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.

38. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 29 .

39. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 30 .

40. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 31 .

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Nov 29, 2022
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 063141/0155 →
Continuity (3)
Provisional Application 6053130000 · Dec 19, 2003
Provisional Application 6059839700 · Aug 3, 2004
Related Publication 20070197391A1 · Aug 23, 2007