Surfactants for agricultural products

Patent metadata

Field	Value
Publication number	US-11992008-B2
Application number	US-202117196874-A
Country	US
Kind code	B2
Filing date	Mar 9, 2021
Priority date	Mar 11, 2020
Publication date	May 28, 2024
Grant date	May 28, 2024

Abstract

Agricultural products, such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides, may be formulated to include one or more surfactants, from one or more surfactant classes, such as derivatives of amino acids that have surface-active properties.

First claim

The invention claimed is:

1. A formulation for a pesticide, comprising:
at least one surfactant of Formula I,

wherein R′ and R 2 may be the same or different, and may be selected from the group consisting of hydrogen and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is 5;
m is 11;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
an optional counterion associated with the compound which, if present, is hydroxide; and
a pesticide.

2. The formulation of claim 1 , further comprising a water-insoluble solvent.

3. The formulation of claim 1 , wherein the surfactant comprises at least one of;
dodecyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

and combinations thereof.

4. The formulation of claim 1 , wherein the pesticide is an insecticide.

5. The formulation of claim 4 , further comprising an antifoaming agent.

6. The formulation of claim 4 , further comprising an antifreezing agent.

7. The formulation of claim 4 , further comprising water.

8. The formulation of claim 4 , wherein the surfactant comprises at least one of;
dodecyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

and combinations thereof.

9. A formulation for a fungicide, comprising:
at least one surfactant of Formula I,

wherein R′ and R 2 may be the same or different, and may be selected from the group consisting of hydrogen and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is 5;
m is 11;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
an optional counterion associated with the compound which, if present, is hydroxide; and
a fungicide.

10. The formulation of claim 9 , further comprising a co-surfactant.

11. The formulation of claim 9 , further comprising a carrier agent.

12. The formulation of claim 9 , wherein the surfactant comprises at least one of;
dodecyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

and combinations thereof.

13. A formulation for an herbicide, comprising:
at least one surfactant of Formula I,

wherein R′ and R 2 may be the same or different, and may be selected from the group consisting of hydrogen and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is 5;
m is 11;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
an optional counterion associated with the compound which, if present, is hydroxide; and
an herbicide.

14. The formulation of claim 13 , further comprising a second herbicide.

15. The formulation of claim 13 , further comprising a water-insoluble solvent.

16. The formulation of claim 13 , further comprising water.

17. The formulation of claim 13 , wherein the surfactant comprises at least one of;
dodecyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

and combinations thereof.

Assignees

• Advansix Resins & Chemicals Llc

Inventors

• Asirvatham Edward

Classifications

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• A01N37/44

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids · CPC title

• A01N41/08

  Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof · CPC title

• C07C229/10 Primary

  the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title