N-phosphonomethylglycine guanidine derivative salts

Patent metadata

Field	Value
Publication number	US-9233993-B2
Application number	US-201013381457-A
Country	US
Kind code	B2
Filing date	Jun 24, 2010
Priority date	Jun 30, 2009
Publication date	Jan 12, 2016
Grant date	Jan 12, 2016

Abstract

The present invention provides N-phosphonomethylglycine guanidine salts. The N-phosphonomethylglycine guanidine salts have improved herbicidal efficacy over glyphosate alone. The present invention also provides guanidine compounds and salts thereof.

First claim

What is claimed is:

1. A salt of N-phosphonomethylglycine having the formula:

wherein R 1 , R 2 and R 3 are independently hydrogen, sodium, potassium, ammonium, isopropylamine, n-propylamine, monoethanolamine, diethanolamine, dimethylamine, or a guanidine derivative having the formula:

provided that at least one of R 1 , R 2 and R 3 is the guanidine derivative;
R 4 is —(CH 2 ) m —(NR 9 (CH 2 ) n ) x —NR 10 R 11 or —(CH 2 ) m —CH(NH 2 )CH(NH 2 )R 11 , polyethyleneimino, C 12 -C 18 alkyl, or C 12 -C 18 alkenyl;
R 5 , R 6 , R 7 and R 8 are independently hydrogen or C 1 -C 5 hydrocarbyl;
R 9 and R 10 are independently hydrogen or C 1 -C 5 hydrocarbyl;
R 11 is C 1 -C 30 hydrocarbyl; and
m, n and x are independently an integer from 1 to 10.

2. The compound of claim 1 wherein said salt is a monobasic salt.

3. The compound of claim 1 wherein said salt is a dibasic salt.

4. The compound of claim 1 wherein said salt is a tribasic salt.

5. The compound of claim 1 wherein R 5 , R 6 , R 7 and R 8 are independently hydrogen or C 1 -C 5 alkyl.

6. The compound of claim 1 wherein R 4 is 3,6,9,12,15,18-hexaazatriacontyl or tallow(2,3-diaminopropyl) and R 5 , R 6 , R 7 and R 8 are hydrogen.

7. The compound of claim 1 wherein R 4 is 3,6,9,12,15,18-hexaazatriacontyl or tallow(2,3-diaminopropyl) and R 5 , R 6 , R 7 and R 8 are methyl.

8. The compound of claim 1 wherein R 4 is polyethyleneimino and R 5 , R 6 , R 7 and R 8 are hydrogen.

9. The compound of claim 1 wherein R 4 is polyethyleneimino and R 5 , R 6 , R 7 and R 8 are methyl.

10. The compound of claim 1 wherein R 4 is dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, coco, tallow, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or octadecenyl, and R 5 , R 6 , R 7 and R 8 are methyl.

11. The compound of claim 1 wherein R 4 is dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, coco, tallow, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or octadecenyl, and R 5 , R 6 , R 7 and R 8 are hydrogen.

12. The compound of claim 1 wherein one of R 1 , R 2 and R 3 is the guanidine derivative, one of R 1 , R 2 and R 3 is sodium, potassium, ammonium, isopropylamine, n-propylamine, monoethanolamine, diethanolamine, or dimethylamine, and the other of R 1 , R 2 and R 3 is hydrogen, sodium, potassium, ammonium, isopropylamine, n-propylamine, monoethanolamine, diethanolamine, or dimethylamine.

13. An aqueous herbicidal composition comprising the salt of N-phosphonomethylglycine of claim 1 .

14. The aqueous herbicidal composition of claim 13 comprising from about 300 to about 600 grams per liter N-phosphonomethylglycine on an acid equivalent basis.

15. The aqueous herbicidal composition of claim 14 comprising from about 420 to about 600 grams per liter N-phosphonomethylglycine on an acid equivalent basis.

16. The aqueous herbicidal composition of claim 15 comprising from about 480 to about 540 grams per liter N-phosphonomethylglycine on an acid equivalent basis.

17. The aqueous herbicidal composition of claim 13 further comprising at least one surfactant.

18. The aqueous herbicidal composition of claim 13 comprising from about 1 to about 50 grams per liter N-phosphonomethylglycine on an acid equivalent basis.

19. The aqueous herbicidal composition of claim 13 comprising from about 1% to about 50% by weight of N-phosphonomethylglycine on an acid equivalent basis.

20. The aqueous herbicidal composition of claim 13 further comprising at least one co-herbicide.

21. The aqueous herbicidal composition of claim 20 wherein the co-herbicide is a water-soluble co-herbicide selected from the group consisting of acifluorfen, acrolein, amitrole, asulam, benazolin, bentazon, bialaphos, bromacil, bromoxynil, chloramben, chloroacetic acid, clopyralid, 2,4-D, 2,4-DB, dalapon, dicamba, dichlorprop, difenzoquat, diquat, endothall, fenac, fenoxaprop, flamprop, flumiclorac, fluoroglycofen, flupropanate, fomesafen, fosamine, glufosinate, imazameth, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, mecoprop, methylarsonic acid, naptalam, nonanoic acid, paraquat, picloram, quinclorac, sulfamic acid, 2,3,6-TBA, TCA, triclopyr and water-soluble salts thereof.

22. The aqueous herbicidal composition of claim 20 wherein the co-herbicide is of limited water solubility and is selected from the group consisting of acetochlor, aclonifen, alachlor, ametryn, amidosulfuron, anilofos, atrazine, azafenidin, azimsulfuron, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benzofenap, bifenox, bromobutide, bromofenoxim, butachlor, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, chlomethoxyfen, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinmethylin, cinosulfuron, clethodim, clodinafop-propargyl, clomazone, clomeprop, cloransulam-methyl, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, daimuron, desmedipham, desmetryn, dichlobenil, diclofop-methyl, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, dinoterb, diphenamid, dithiopyr, diuron, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenuron, flamprop-methyl, flazasulfuron, fluazifop-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluorochloridone, fluoroglycofen-ethyl, flupoxam, flurenol, fluridone, fluroxypyr-1-methylheptyl, flurtamone, fluthiacet-methyl, fomesafen, halosulfuron, haloxyfop-methyl, hexazinone, imazamox, imazosulfuron, indanofan, isoproturon, isouron, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxyfluorfen, pebulate, pendimethalin, pentanochlor, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron, prodiamine, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen-ethyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyributicarb, pyridate, pyriminobac-methyl, quinclorac, quinmerac, quizalofop-ethyl, rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron, sulfosulfuron, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron, thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron, trietazine, trifluralin, triflusulfuron and vernolate.

23. A solid herbicidal composition comprising the salt of N-phosphonomethylglycine of claim 1 .

24. The solid herbicidal composition of claim 23 comprising from about 10% to about 80% by weight of N-phosphonomethylglycine on an acid equivalent bas

Assignees

• Brinker Ronald J
• Soula Olivier
• Lemercier Alain
• Monsanto Technology Llc
• Flamel Tech Sa

Inventors

• Brinker Ronald J
• Soula Olivier
• Lemercier Alain

Classifications

• C07C279/02

  Guanidine; Salts, complexes or addition compounds thereof · CPC title

• C07C279/04

  having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title

• A01N57/20 Primary

  containing acyclic or cycloaliphatic radicals · CPC title

• C07C279/12

  being further substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title