Auxin herbicidal mixtures

• US 10,485,232 B2
• Filed: 07/20/2017
• Issued: 11/26/2019
• Est. Priority Date: 11/05/2012
• Status: Active Grant

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Wright, Daniel R., Zhang, Junhua
• Primary Examiner(s): Richter, Johann R
• Assistant Examiner(s): Sullivan, Danielle
• Application Number:
  US15/654,883
• Publication Number:
  US 20180007896A1
• Time in Patent Office: 859 Days
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/42 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals

Abstract

Herbicidal mixtures comprising an auxin herbicide and an adjuvant comprising a salt having a quaternary ammonium cation and/or a phosphonium cation are described. The adjuvant reduces the volatility of the auxin herbicide and/or counteracts the negative impact on the volatility of the auxin herbicide caused by the addition of a co-herbicide. Methods of preparing the herbicidal mixtures are also described.

Claims

1. A method of preparing a herbicidal mixture, the method comprising:

combining an auxin herbicide comprising a first cation and an adjuvant comprising a salt comprising a second cation, wherein the salt is selected from the group consisting of;

(a) an ammonium salt of Formula I

27. The method of claim 1 wherein the molar ratio of auxin herbicide to salt of Formula I, II, and/or III is from about 1:

1 to about 3;

1.

2. A herbicidal mixture, comprising:

an auxin herbicide comprising a first cation and an adjuvant comprising a salt comprising a second cation, wherein the salt is selected from the group consisting of;

(a) an ammonium salt of Formula I

3. The herbicidal mixture of claim 2 wherein the adjuvant comprises an ammonium salt of Formula I

4. The herbicidal mixture of claim 3 wherein X is Cl.

5. The herbicidal mixture of claim 3 wherein X is Br.

6. The herbicidal mixture of claim 3 wherein X is OH.

7. The herbicidal mixture of claim 2 wherein the molar ratio of auxin herbicide to salt of Formula I is from about 1:

1 to about 3;

1.

8. The herbicidal mixture of claim 2 wherein the adjuvant comprises a salt containing a nitrogen heterocycle of Formula II

9. The herbicidal mixture of claim 8 wherein A is a substituted imidazole ring, a substituted pyridine ring, or a substituted pyrrolidine ring;

R⁵ is C₁-C₁₂ alkyl; and

/or

the salt of Formula II is selected from the group consisting of 1-butyl-1-methyl-pyrrolidinium chloride, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, cetylpyridinium chloride, and cetylpyridinium bromide.

10. The herbicidal mixture of claim 3 wherein the salt of Formula I is selected from the group consisting of tetrabutylammonium chloride and tetrabutylammonium bromide.

11. The herbicidal mixture of claim 2 wherein the adjuvant comprises a phosphonium salt of Formula III

12. The herbicidal mixture of claim 11 wherein R⁷, R⁸, R⁹, and R¹⁰ are independently C₁-C₁₂ alkyl;

and/or

the salt of Formula III comprises tetrabutylphosphonium chloride.

13. The herbicidal mixture of claim 2 wherein X is Cl, Br, or OH.

14. The herbicidal mixture of claim 2 wherein the auxin herbicide is selected from the group consisting of 3,6-dichloro-2-methoxybenzoic acid (dicamba);

2,4-dichlorophenoxyacetic (2,4-D);

4-(2,4-dichlorophenoxy)butanoic acid (2,4-DB);

2-(2,4-dichlorophenoxy)propanoic acid (dichloroprop);

2-(4-chloro-2-methylphenoxy)acetic acid (MCPA);

4-(4-chloro-2-methylphenoxy)butanoic acid (MCPB);

4-amino-3,6-dichloro-2-pyridinecarboxylic acid (aminopyralid);

3,6-dichloro-2-pyridinecarboxylic acid (clopyralid);

2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid (fluroxypyr);

[(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid (triclopyr);

2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop);

4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid (picloram);

3,7-dichloro-8-quinolinecarboxylic acid (quinclorac);

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (aminocyclopyrachlor);

agriculturally acceptable salts or other derivatives of any of these herbicides;

racemic mixtures and resolved isomers thereof; and

mixtures thereof.

15. The herbicidal mixture of claim 2 wherein the auxin herbicide comprises a salt of dicamba selected from the group consisting of the monoethanolamine salt, diethanolamine salt, isopropylamine, diglycolamine salt, potassium salt, sodium salt dimethylamine salt and mixtures thereof.

16. The herbicidal mixture of claim 2 wherein the auxin herbicide comprises a salt of 2,4-D.

17. The herbicidal mixture of claim 2 wherein the herbicidal mixture further comprises a co-herbicide selected from the group consisting of N-(phosphonomethyl)glycine (glyphosate);

DL-phosphinothricin (glufosinate);

atrazine, acetochlor, fomesafen, flumioxazin, lactofen, sulfentrazone, metribuzin, clethodim, sethoxydim, metolachlor, alachlor, fenoxaprop, fluazifop, haloxyfop-methyl, paraquat, trialkoxydim; and

salts and combinations thereof.

18. The herbicidal mixture of claim 17 wherein the co-herbicide comprises a salt of glyphosate.

19. The herbicidal mixture of claim 2 wherein the pH of the herbicidal mixture is from about 4 to about 5.5.

20. The herbicidal mixture of claim 2 wherein the herbicidal mixture further comprises a surfactant selected from the group consisting of alkoxylated tertiary etheramines, alkoxylated quaternary etheramines, alkoxylated etheramine oxides, alkoxylated tertiary amines, alkoxylated quaternary amines, alkoxylated polyamines, sulfates, sulfonates, phosphate esters, alkyl polysaccharides, alkoxylated alcohols, amidoalkylamines and combinations thereof.

21. The herbicidal mixture of claim 2 wherein the herbicidal mixture is a concentrate composition wherein the total herbicide content is from about 10 wt. % a.e. to about 40 wt. % a.e.

22. The herbicidal mixture of claim 2 wherein the herbicidal mixture is an application mixture wherein the total herbicide content is from about 0.1 wt. % a.e. to about 10 wt. % a.e.

23. The herbicidal mixture of claim 22 wherein the herbicidal mixture further comprises a co-herbicide and the concentration of the co-herbicide in the application mixture is from about 0.5 wt. % a.e. to about 8 wt. % a.e.

25. The herbicidal mixture of claim 2 wherein the concentration of the adjuvant in the herbicidal mixture is from about 0.1 wt. % to about 10.0 wt. %.

26. The herbicidal mixture of claim 2 wherein the molar ratio of auxin herbicide to salt of Formula I, II, and/or III is from about 1:

1 to about 3;

1.

24. The herbicidal mixture of 22 wherein the concentration of the auxin herbicide in the herbicidal mixture is from about 0.25 wt. % (a.e.) to about 4 wt. % (a.e.).