IP Library Granted Patent US 12,356,993
Granted Patent B2
US 12,356,993 · App. 17/619,311 · Granted Jul 15, 2025

Stable herbicidal compositions comprising amine oxide and betaine

Inventors: Zixian Chen (Singapore, SG); Yuming Zhou (Jiangsu, CN); Paige Lana O'Brien (North Parramatta, AU); Renato Monterosso (Victoria, AU)
Assignee: SPECIALTY OPERATIONS FRANCE
A01N57/20A01N25/02A01N25/30
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Quick Facts
Patent No.
US 12,356,993
App. No.
17/619,311
Granted
Jul 15, 2025
Kind
B2
Abstract

Provided is a herbicidal composition comprising high load aminophosphate or aminophosphonate salts, in particular high load glyphosate salts, wherein the composition comprises a surfactant mixture of at least an C 8 -C 10 amine oxide and a betaine surfactant. The composition has good low temperature stability (i.e., no crystal formation or phase separation) among other beneficial properties.

Claims (56)

1. An aqueous herbicidal composition comprising:

at least two aminophosphate or aminophosphinate salts in a total amount of equal or greater than 560 g/L (ae);

an amine oxide surfactant of the formula:

R 1 —N + R 2 R 3 —O −   (I)

wherein R 1 is a C 8 -C 10 , linear or branched, alkyl or hydroxyalkyl; R 2 and R 3 is independently a C 1 -C 4 alkyl or hydroxyalkyl; and

a betaine surfactant of the formula:

R 4 R 5 R 6 N + (CH 2 ) x C(O)O −   (II)

wherein R 4 is a C 1 -C 4 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

R 5 is a C 6 -C 22 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

R 6 is a C 1 -C 4 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl, or a C 6 -C 22 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

x is an integer of 1-3;

wherein any two of the groups R 4 -R 6 may optionally form a ring structure, and

wherein said aminophosphate or aminophosphinate salts are glyphosate salts.

2. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are present at equal or greater than 600 g/L (ae).

3. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are selected from the group consisting of glyphosate potassium (K) salt, glyphosate sodium (Na) salt, glyphosate isopropylamine (IPA) salt, glyphosate monoethanolamine (MEA) salt, glyphosate monomethylamine (MMA) salt, glyphosate triethylamine (TEA) salt, glyphosate dimethylamine (DMA) salt, glyphosate trimethylsulphonium salt, and glyphosate ammonium (NH 3 ) salt.

4. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate potassium salt and glyphosate isopropylammonium salt.

5. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate potassium salt and glyphosate ammonium salt.

6. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate isopropylammonium salt and glyphosate monoethanolammonium salt.

7. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate isopropylammonium salt and glyphosate ammonium salt.

8. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate potassium salt, glyphosate monomethylamine salt and glyphosate ammonium salt.

9. The aqueous herbicidal composition of claim 1 , wherein said aminophosphate or aminophosphinate salts are glyphosate monomethylamine salt, glyphosate isopropylammonium salt and glyphosate ammonium salt.

10. The aqueous herbicidal composition of claim 1 , wherein said amine oxide surfactant is according to:

R 7 —N + (CH 3 ) 2 —O −   (III)

wherein R 7 is a C 8 -C 10 , linear or branched, alkyl or hydroxyalkyl.

11. The aqueous herbicidal composition of claim 1 , wherein said betaine surfactant is according to the general formula:

R 4 R 5 R 6 N + (CH 2 ) x C(O)O −   (II)

wherein R 4 and R 6 is independently a C 1 -C 4 alkyl;

x=1;

R 5 is a C 6 -C 22 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl.

12. The aqueous herbicidal composition of claim 1 , wherein said amine oxide surfactant is octyl dimethyl amine oxide or decyl dimethyl amine oxide.

13. The aqueous herbicidal composition of claim 1 , wherein weight ratio of said amine oxide surfactant and said betaine surfactant is in the range of from 30/70 to 70/30.

14. The aqueous herbicidal composition of claim 1 , wherein said amine oxide surfactant is present in an amount of from 0.1 wt % to 10 wt %, based on the total weight of the aqueous herbicidal composition.

15. The aqueous herbicidal composition of claim 1 , wherein said betaine surfactant is present in an amount of from 0.1 wt % to 10 wt %, based on the total weight of the aqueous herbicidal composition.

16. The aqueous herbicidal composition of claim 1 , wherein the composition further comprises choline chloride.

17. A method for regulating plant growth comprising contacting an aqueous herbicidal composition according to claim 1 , with a plant.

18. A method for enhancing the storage stability of an aqueous herbicidal composition comprising at least two aminophosphate or aminophosphinate salts in a total amount of equal or greater than 560 g/L (ae), wherein the method comprises the step of adding to the composition a surfactant mixture of at least:

an amine oxide surfactant of the formula:

R 1 —N + R 2 R 3 —O −   (I)

wherein R 1 is a C 8 -C 10 , linear or branched, alkyl or hydroxyalkyl; R 2 and R 3 is independently a C 1 -C 4 alkyl or hydroxyalkyl; and

a betaine surfactant of the formula:

R 4 R 5 R 6 N + (CH 2 ) x C(O)O −   (II)

wherein R 4 is a C 1 -C 4 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

R 5 is a C 6 -C 22 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

R 6 is a C 1 -C 4 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl, or a C 6 -C 22 alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl;

x is an integer of 1-3;

wherein any two of the groups R 4 -R 6 may optionally form a ring structure, and

wherein said aminophosphate or aminophosphinate salts are glyphosate salts.

19. The aqueous herbicidal composition of claim 1 , wherein for the amine oxide surfactant of formula R 1 —N + R 2 R 3 —O − (I):

R 1 is a C 8 -C 10 , linear or branched, alkyl and

R 2 and R 3 is independently a C 1 -C 4 alkyl,

and wherein for the betaine surfactant of the formula R 4 R 5 R 6 N + (CH 2 ) x C(O) O″ (II):

R 4 is a C 1 -C 4 alkyl;

R 5 is a C 6 -C 22 alkyl;

R 6 is a C 1 -C 4 alkyl; and

x is an integer of 1-3.

20. The aqueous herbicidal composition of claim 1 , wherein the composition is stable at low temperatures ranging from equal to or less than 5° C. to 20° C.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
Priority Claims (1)
WO PCT/CN2019/095673 · Jul 12, 2019 · international
Continuity (1)
Related Publication 20220295796A1 · Sep 22, 2022
References Cited (9)
US 5703016A · Magin · 1997 [cited by examiner]
US 20140194289A1 · Sclapari · 2014 [cited by examiner]
EP 1830652B1 · 2013 [cited by applicant]
WO 0108482A1 · 2001 [cited by applicant]
WO 2006069794A2 · 2006 [cited by applicant]
WO 2007054540A2 · 2007 [cited by applicant]
WO 2009060026A2 · 2009 [cited by applicant]
WO 2011029561A2 · 2011 [cited by applicant]
WO 2017027668A1 · 2017 [cited by applicant]