IP Library Granted Patent US 11,905,304
Granted Patent B2
US 11,905,304 · App. 17/118,312 · Granted Feb 20, 2024

Surfactants for agricultural products

Inventor: Edward Asirvatham (Chatham, NJ)
Assignee: AdvanSix Resins & Chemicals LLC
C07F7/0838A01N25/04A01N25/30
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Quick Facts
Patent No.
US 11,905,304
App. No.
17/118,312
Granted
Feb 20, 2024
Kind
B2
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 siloxane derivatives of amino acids that have surface-active properties.

Claims (55)

1. A formulation for a pesticide, comprising:

at least one surfactant of Formula I,

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;

n is an integer from 3 to 12;

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;

an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and

a pesticide.

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

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

4. The formulation of claim 3 , further comprising an antifoaming agent.

5. The formulation of claim 3 , further comprising an antifreezing agent.

6. The formulation of claim 3 , further comprising water.

7. A formulation for a fungicide, comprising:

at least one surfactant of Formula I,

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;

n is an integer from 3 to 12;

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;

an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and

a fungicide.

8. The formulation of claim 7 , further comprising a co-surfactant.

9. The formulation of claim 7 , further comprising a carrier agent.

10. A formulation for an herbicide, comprising:

at least one surfactant of Formula I,

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;

n is an integer from 3 to 12;

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;

an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and

an herbicide.

11. The formulation of claim 10 , further comprising a second herbicide.

12. The formulation of claim 10 , further comprising a water-insoluble solvent.

13. The formulation of claim 10 , further comprising water.

14. The formulation of claim 1 , wherein n=5.

15. The formulation of claim 7 , wherein n=5.

16. The formulation of claim 10 , wherein n=5.

17. The formulation of claim 1 , wherein the surfactant comprises at least one of:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexanamide, having the following formula:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexaminium chloride, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

5-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -6-oxohexyl)dimethylammonio)pentane-1-sulfonate, having the following formula:

18. The formulation of claim 7 , wherein the surfactant comprises at least one of:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexanamide, having the following formula:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexaminium chloride, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -N,N,N-trimethyl-6-oxohexan-1-aminiumiodide, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

5-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -6-oxohexyl)dimethylammonio)pentane-1-sulfonate, having the following formula:

19. The formulation of claim 10 , wherein the surfactant comprises at least one of:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexanamide, having the following formula:

6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)hexaminium chloride, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan -3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

5-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino) -6-oxohexyl)dimethylammonio)pentane-1-sulfonate, having the following formula:

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2022
From: ASIRVATHAM, EDWARD
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 061102/0645 →
SECURITY INTEREST Recorded Oct 27, 2021
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: TRUIST BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 057940/0794 →
Continuity (2)
Provisional Application 62950391 · Dec 19, 2019
Related Publication 20210188882A1 · Jun 24, 2021
Cited By (2)
US 12,459,963 US 12,466,846