Auxin herbicidal mixtures

Patent metadata

Field	Value
Publication number	US-10485232-B2
Application number	US-201715654883-A
Country	US
Kind code	B2
Filing date	Jul 20, 2017
Priority date	Nov 5, 2012
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

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.

First claim

What is claimed is:

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

wherein R 1 , R 2 , R 3 , and R 4 are each butyl and X is an agronomically acceptable anion;
(b) a salt containing a nitrogen heterocycle of Formula II

wherein A is a 5 or 6-membered heterocyclic ring; R 5 is a C 1 -C 20 alkyl; R 6 is hydrogen or a C 1 -C 6 alkyl, and X is an agronomically acceptable anion;
(c) a phosphonium salt of Formula III

wherein R 7 , R 8 , R 9 , and R 10 are independently a C 1 -C 12 hydrocarbyl and X is an agronomically acceptable anion; and mixtures thereof, and wherein the herbicidal mixture has a total herbicide concentration no greater than about 40% by weight acid equivalent (a.e).

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

wherein R 1 , R 2 , R 3 , and R 4 are each butyl and X is an agronomically acceptable anion;
(b) a salt containing a nitrogen heterocycle of Formula II

wherein A is a 5 or 6-membered heterocyclic ring; R 5 is a C 1 -C 20 alkyl; R 6 is hydrogen or a C 1 -C 6 alkyl, and X is an agronomically acceptable anion;
(c) a phosphonium salt of Formula III

wherein R 7 , R 8 , R 9 , and R 10 are independently a C 1 -C 12 hydrocarbyl and X is an agronomically acceptable anion; and mixtures thereof, and wherein the herbicidal mixture has a total herbicide concentration no greater than about 40% by weight acid equivalent (a.e).

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

wherein R 1 , R 2 , R 3 , and R 4 are each butyl and X is an agronomically acceptable anion.

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

wherein A is a 5 or 6-membered heterocyclic ring; R 5 is a C 1 -C 20 alkyl; R 6 is hydrogen or a C 1 -C 6 alkyl, and X is an agronomically acceptable anion.

9. The herbicidal mixture of claim 8 wherein A is a substituted imidazole ring, a substituted pyridine ring, or a substituted pyrrolidine ring;
R 5 is C 1 -C 12 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

wherein R 7 , R 8 , R 9 , and R 10 are independently a C 1 -C 12 hydrocarbyl and X is an agronomically acceptable anion.

12. The herbicidal mixture of claim 11 wherein R 7 , R 8 , R 9 , and R 10 are independently C 1 -C 12 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 c

Assignees

• Monsanto Technology Llc

Inventors

• Wright Daniel R
• Zhang Junhua

Classifications

• A01N57/20

  containing acyclic or cycloaliphatic radicals · CPC title

• A01N25/00 Primary

  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 title

• A01N43/40

  six-membered rings · CPC title

• A01N33/12 Primary

  Quaternary ammonium compounds · CPC title

• A01N37/40

  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 title