Guanidine derivative compounds

Patent metadata

Field	Value
Publication number	US-9775355-B2
Application number	US-201514966256-A
Country	US
Kind code	B2
Filing date	Dec 11, 2015
Priority date	Jun 30, 2009
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention provides guanidine compounds and salts thereof that may be useful, for example, in the preparation of herbicidal compositions. The compounds may be used, for example, to prepare N-phosphonomethylglycine guanidine salts having improved herbicidal efficacy over glyphosate alone.

First claim

What is claimed is:

1. A guanidine compound or a salt thereof having the formula:

wherein R 4 is —(CH 2 ) m —(NR 9 (CH 2 ) n ) x —NR 10 R 11 , —(CH 2 ) m —CH(NH 2 )CH(NH 2 )R 11 or polyethyleneimino; 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 R 5 , R 6 , R 7 and R 8 are independently hydrogen or C 1 -C 5 alkyl.

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

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

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

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

7. An aqueous herbicidal composition comprising the compound of claim 1 and an herbicide component comprising one or more herbicides.

8. The composition of claim 7 wherein the herbicide component comprises glyphosate.

9. The composition of claim 7 wherein the herbicide component comprises one or more water-soluble herbicides 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.

10. The composition of claim 9 wherein the herbicide component comprises dicamba.

11. The composition of claim 9 wherein the herbicide component comprises 2,4-D.

12. The composition of claim 7 wherein the herbicide component comprises one or more herbicides of limited water solubility 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.

13. The composition of claim 8 comprising from about 1% to about 50% by weight of glyphosate on an acid equivalent basis.

14. The composition of claim 8 wherein the composition is an aqueous herbicidal concentrate comprising from about 300 to about 600 grams per liter glyphosate on an acid equivalent basis.

15. The composition of claim 8 wherein the composition is an aqueous herbicidal concentrate comprising from about 420 to about 600 grams per liter glyphosate on an acid equivalent basis.

16. The composition of claim 8 wherein the composition is an aqueous herbicidal concentrate comprising from about 480 to about 540 grams per liter glyphosate on an acid equivalent basis.

17. The composition of claim 8 wherein the composition is a ready-to-use aqueous composition comprising from about 1 to about 50 grams per liter glyphosate on an acid equivalent basis.

18. The composition of claim 8 wherein the composition is a solid herbicidal composition comprising from about 10% to about 80% by weight of glyphosate on an acid equivalent basis.

19. The composition of claim 7 further comprising at least one surfactant.

20. A guanidine compound or a salt thereof having the formula:

wherein R 5 , R 6 , R 7 and R 8 are independently hydrogen or C 1 -C 5 hydrocarbyl, R 12 is hydrogen, C 8 -C 30 alkyl, or C 8 -C 30 alkenyl, and x and y are independently an integer from 2 to 20.

21. The compound of claim 20 wherein R 5 , R 6 , R 7 and R 8 are independently hydrogen or C 1 -C 5 alkyl.

22. The compound of claim 20 wherein R 12 is C 12 -C 18 alkyl or C 12 -C 18 alkenyl.

23. The compound of claim 20 wherein the compound has a weight average molecular weight of from about 500 to about 7,000.

24. An aqueous herbicidal composition comprising the compound of claim 20 and an herbicide component comprising one or more herbicides.

25. The composition of claim 24 wherein the herbicide component comprises glyphosate.

26. The composition of claim 24 wherein the herbicide component comprises one or more water-soluble herbicides 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, glu

Assignees

• Monsanto Technology Llc
• Flamel Tech

Inventors

• Brinker Ronald J
• Soula Olivier
• Lemercier Alain

Classifications

• C07C279/02

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

• A01N47/44 Primary

  Guanidine; Derivatives thereof · CPC title

• C07C279/04

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

• C07C279/20

  containing any of the groups [IMAGE cpc-sch-C07C-0971.gif], X being a hetero atom, Y being any atom, e.g. acylguanidines · CPC title

• C07F9/3817

  Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se) · CPC title