IP Library Granted Patent US 11,744,244
Granted Patent B2
US 11,744,244 · App. 14/014,730 · Granted Sep 5, 2023

Compositions and methods for improving the compatibility of water soluble herbicide salts

Inventors: Mark Alexander (Fort Worth, TX); Anne Austin (Signal Mountain, TN); Alex Kennedy (Indianapolis, IN); Lei Liu (Carmel, IN); Klin A. Rodrigues (Signal Mountain, TN); Holger Tank (Zionsville, IN)
Assignees: CORTEVA AGRISCIENCE LLC; NOURYON CHEMICALS INTERNATIONAL B.V.
A01N25/00A01N25/30A01N39/04
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Quick Facts
Patent No.
US 11,744,244
App. No.
14/014,730
Granted
Sep 5, 2023
Kind
B2
Abstract

Methods and compositions for improving the compatibility of aqueous herbicide solutions containing at least one of a water soluble salt of an aryloxyalkanoic acid, a water soluble salt of a pyridyloxyalkanoic acid, and a water soluble salt of glyphosate, and optionally ≤16% of one or more fertilizers, such as ammonium sulfate, by adding certain polymeric crystallization inhibitors are provided.

Claims (46)

1. A method of improving the compatibility of an aqueous herbicide solution including: an aqueous solution comprising a) (2,4-dicholorophenoxy)acetic acid; b) one or more inorganic cations selected from the group consisting of Na + , K + , Ca 2+ , Mg 2+ , Fe 2+ , Fe 3+ , Mn 2+ , and Zn 2+ and/or one or more organo ammonium cations selected from the group consisting of monomethyl ammonium, isopropyl ammonium, butyl ammonium, dimethyl ammonium, diethyl ammonium, dimethylethyl ammonium, diethyethanol ammonium, triethanol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium and N,N,N-trimethylethanol ammonium (choline), and cations made from dimethylaminopropylamine and diethylenetriamine, or mixtures thereof; c) less than 16% of ammonium sulfate; and b) glyphosate; comprising adding to the aqueous herbicide solution one or more polymeric crystallization inhibitors of structure I

wherein A is

wherein R 1 , R 2 , and R 3 are independently H, CH 3 , COOH, or CH 2 COOH, L is a linking group comprising —C(═O)—O—, —CH 2 —, —O—, —O—C(═O)—, or a direct bond, and R hy is hydrophobic and comprises a linear or branched alkyl, cycloalkyl, aryl, alkaryl or alkoxylated derivative thereof;

B is derived from polymerizing an ethylenically unsaturated carboxylic acid monomer and/or its salts; and

C is 0 mole % of the polymeric crystallization inhibitor,

wherein the (2,4-dicholorophenoxy)acetic acid is present in the aqueous solution at a concentration greater than 1% on an acid equivalent basis, and wherein the pH of the aqueous solution is about 6 or lower.

2. The method of claim 1 , wherein R hy is a linear aryl moiety.

3. The method of claim 1 , wherein R hy is naphthyl, ethoxylated naphthyl, phenyl, ethoxylated phenyl, benzyl, or ethoxylated benzyl.

4. The method of claim 1 , wherein the aqueous herbicide solution is a concentrate or a pre-mix concentrate.

5. The method of claim 1 , wherein the aqueous herbicide solution is a spray solution.

6. The method of claim 1 , wherein the polymeric crystallization inhibitor is a co-polymer containing polyacrylate groups, polymethacrylate groups or polymaleate groups, or mixtures thereof.

7. The method of claim 6 , wherein the co-polymer containing polyacrylate groups comprises hydrophobically modified groups derived from the polymerization of an acrylate monomer and a styrene or substituted styrene monomer.

8. The method of claim 1 , wherein the polymeric crystallization inhibitor is in the form of a salt.

9. The method of claim 8 , wherein the salt is an organic amine salt or an inorganic alkaline salt.

10. The method of claim 8 , wherein the salt contains an organo ammonium cation selected from monomethyl ammonium, isopropyl ammonium, butyl ammonium, dimethyl ammonium, diethyl ammonium, triethyl ammonium, monoethanol ammonium, diethanol ammonium, dimethylethyl ammonium, diethylethanol ammonium, triethanol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium and N,N,N-trimethylethanol ammonium (choline), and cations made from dimethylaminopropylamine and diethylenetriamine, or mixtures thereof.

11. The method of claim 1 , wherein the polymeric crystallization inhibitor of structure I comprises 5 to 80 mole % of A and 0 mole % of C with the rest being B.

12. An aqueous herbicide solution of improved compatibility comprising: an aqueous solution comprising: a) (2,4-dicholorophenoxy)acetic acid; b) one or more inorganic cations selected from the group consisting of Na + , K + , Ca 2+ , Mg 2+ , Fe 2+ , Fe 3+ , Cu 2+ , Mn 2+ , and Zn 2+ and/or one or more organo ammonium cations selected from the group consisting of monomethyl ammonium, isopropyl ammonium, butyl ammonium, dimethyl ammonium, diethyl ammonium, dimethylethyl ammonium, diethyethanol ammonium, triethanol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium and N,N,N-trimethylethanol ammonium (choline), and cations made from dimethylaminopropylamine and diethylenetriamine, or mixtures thereof; c) less than 16% ammonium sulfate; d) glyphosate; and f) one or more polymeric crystallization inhibitors of structure I

wherein A is

wherein R 1 , R 2 , and R 3 are independently H, CH 3 , COOH, or CH 2 COOH, L is a linking group comprising —C(═O)—O—, —CH 2 —, —O—, —O—C(═O)—, or a direct bond, and R hy is hydrophobic and comprises a linear or branched alkyl, cycloalkyl, aryl, alkaryl or alkoxylated derivative thereof;

B is derived from polymerizing an ethylenically unsaturated carboxylic acid monomer and/or its salts; and

C is 0 mole % of the polymeric crystallization inhibitor,

wherein the (2,4-dicholorophenoxy)acetic acid is present in the aqueous solution at a concentration greater than 1% on an acid equivalent basis, and wherein the pH of the aqueous solution is about 6 or lower.

13. The aqueous herbicide solution of claim 12 , wherein R hy is a linear aryl moiety.

14. The aqueous herbicide solution of claim 12 , wherein R hy is naphthyl, ethoxylated naphthyl, phenyl, ethoxylated phenyl, benzyl, or ethoxylated benzyl.

15. The aqueous herbicide solution of claim 12 , wherein the polymeric crystallization inhibitor is in the form of a salt.

16. The aqueous herbicide solution of claim 15 , wherein the salt of the crystallization inhibitor is an organic amine salt or an inorganic alkaline salt.

17. The aqueous herbicide solution of claim 15 , wherein the salt of the crystallization inhibitor contains an organo ammonium cation selected from monomethyl ammonium, isopropyl ammonium, butyl ammonium, dimethyl ammonium, diethyl ammonium, triethyl ammonium, monoethanol ammonium, diethanol ammonium, dimethylethyl ammonium, diethylethanol ammonium, triethanol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium, N,N,N-trimethylethanol ammonium (choline), and cations made from dimethylaminopropylamine and diethylenetriamine, or mixtures thereof.

18. The aqueous herbicide solution of claim 12 that is a concentrate or a pre-mix concentrate.

19. The aqueous herbicide solution of claim 12 that is a spray solution.

20. The aqueous herbicide solution of claim 12 , wherein the polymeric crystallization inhibitor is a co-polymer containing polyacrylate groups, polymethacrylate groups or polymaleate groups, or mixtures thereof.

21. The aqueous herbicide solution of claim 20 , wherein the co-polymer containing polyacrylate groups comprises hydrophobically modified groups derived from the polymerization of an acrylate monomer and a styrene or substituted styrene monomer.

22. The aqueous herbicide solution of claim 12 , wherein the polymeric crystallization inhibitor of structure I comprises 5 to 80 mole % of A and 0 mole % of C with the rest being B.

23. An aqueous herbicide solution of improved compatibility comprising: an aqueous solution comprising: a) (2,4-dicholorophenoxy)acetic acid; b) one or more inorganic cations selected from the group consisting of Na + , K + , Ca 2+ , Mg 2+ , Fe 2+ , Fe 3+ , Cu 2+ , Mn 2+ , and Zn 2+ and/or one or more organo ammonium cations selected from the group consisting of monomethyl ammonium, isopropyl ammonium, butyl ammonium, dimethyl ammonium, diethyl ammonium, dimethylethyl ammonium, diethyethanol ammonium, triethanol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium and N,N,N-trimethylethanol ammonium (choline), and cations made from dimethylaminopropylamine and diethylenetriamine, or mixtures thereof; c) less than 16% ammonium sulfate; and d) one or more polymeric crystallization inhibitors of structure I

wherein A is

wherein R 1 , R 2 , and R 3 are independently H, CH 3 , COOH, or CH 2 COOH, L is a linking group comprising —C(═O)—O—, —CH2-, —O—, —O—C(═O)—, or a direct bond, and R hy is hydrophobic and comprises a linear or branched alkyl, cycloalkyl, aryl, alkaryl or alkoxylated derivative thereof;

B is derived from polymerizing an ethylenically unsaturated carboxylic acid monomer and/or its salts; and

C is 0 mole % of the polymeric crystallization inhibitor,

wherein the (2,4-dicholorophenoxy)acetic acid is present in the aqueous solution at a concentration greater than 1% on an acid equivalent basis, and wherein the pH of the aqueous solution is about 6 or lower.

24. A concentrated spray mixture, comprising, an aqueous solution of

0.2 weight percent of a dimethylammonium salt of a polymer, said polymer consisting of;

30 percent benzyl methacrylate, and

70 percent acrylic acid;

an aqueous concentrate of 2,4 D-dimethyl ammonium salt;

an aqueous concentrate of glyphosate potassium salt; and

2.00 weight percent of ammonium sulfate.

25. A spray mixture, comprising the concentrated spray mixture of claim 24 , and additional water.

Assignments (4)
CHANGE OF NAME Recorded Apr 12, 2023
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 063336/0269 →
CHANGE OF NAME Recorded Nov 11, 2022
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 061931/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2019
From: ALEXANDER, MARK; RODRIGUES, KLIN ALOYSIUS; AUSTIN, ANNE
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 048646/0477 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2018
From: KENNEDY, ALEX; LIU, LEI; TANK, HOLGER
To: DOW AGROSCIENCES LLC
Reel/Frame 047524/0103 →