IP Library Granted Patent US 10,654,760
Granted Patent B2
US 10,654,760 · App. 16/207,755 · Granted May 19, 2020

Solvent systems for dicyandiamide and/or alkyl thiophosphoric triamide and use in agricultural applications

Inventors: Michelle McKnight (Philadelphia, PA); Antoine Vielliard (Paris, FR); Marivi Ortiz-Suarez (Burlington, NJ); Samantha Armisen (Villenave d'Ornon, FR); Chloe Moreau (La Plaine Saint Denis, FR)
Assignee: RHODIA OPERATIONS
C05G3/08C05C9/00C05C11/00C05G3/0064C09K15/28Y02P60/218
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Quick Facts
Patent No.
US 10,654,760
App. No.
16/207,755
Granted
May 19, 2020
Kind
B2
Abstract

An inhibitor composition contains dicyandiamide as a nitrification inhibitor, alkyl thiophosphoric triamide as a urease inhibitor, or a combination thereof, dissolved in a liquid medium comprising an organic solvent selected from, among others, one or more polar aprotic solvents, including one or more organophosphates, amine solvents, heterocyclic alcohol solvents, and mixtures thereof, is useful in making fertilizer compositions and in a method of fertilizing target plants.

Claims (184)

1. A liquid agricultural composition consisting of:

a urease inhibitor comprising N-butyl thiophosphoric triamide, wherein the N-(n-butyl)-thiophosphoric triamide is 30 to 60 wt %, by total weight of the composition;

an organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from C 1 -C 4 alkyl group,

dimethylsulfoxide;

optionally, dicyandiamide;

optionally, water;

optionally, a dye; and

optionally, at least one organic co-solvent selected from:

at least one dibasic ester;

at least one compound of formula (IIa):

R 3 OOC-A-CONR 4 R 5   (IIa),

wherein R 3 comprises a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually comprise a C 1 -C 36 alkyl group, wherein R 4 and R 5 can optionally together form a ring; and wherein A is a linear or a branched divalent C 2 -C 6 alkyl group;

at least one alkyldimethylamide;

ethyl levulinate;

at least one alkylene carbonate; or

any combination thereof

wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent, and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

2. The liquid agricultural composition of claim 1 , wherein the dicyandiamide is present.

3. The liquid agricultural composition of claim 1 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide;

optionally the water; and

optionally, the dye.

4. The liquid agricultural composition of claim 1 , wherein the organophosphate solvent is of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from C 2 -C 4 alkyl group,

wherein the dimethylsulfoxide is present in an amount of at least 39.7 wt %, by total weight of the composition, wherein the N-butyl thiophosphoric triamide is greater than 45 and up to 55 wt % by total weight of the composition.

5. The liquid agricultural composition of claim 4 , wherein the N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the composition.

6. The liquid agricultural composition of claim 1 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide;

optionally the co-solvent; and

optionally, the dye.

7. The liquid agricultural composition of claim 1 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide; and

optionally, the dye.

8. A method of making a solid or concentrated liquid fertilizer composition comprising treating one or more nitrogenous fertilizer compounds with a liquid inhibitor composition consisting of:

N-(n-butyl)-thiophosphoric triamide dispersed in a liquid medium,

wherein the N-(n-butyl)-thiophosphoric triamide is 30 to 60 wt %, by total weight of the liquid inhibitor composition,

the liquid medium consisting of:

at least one organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 2 -C 4 alkyl group,

dimethylsulfoxide,

optionally, dicyandiamide;

optionally, water;

optionally, a dye; and

optionally a co-solvent selected from:

at least one dibasic ester selected from the group consisting of di(C 1 -C 12 )alkyl esters of saturated linear or branched (C 2 -C 8 )aliphatic dicarboxylic acids or mixtures thereof;

at least one compound of formula (IIa):

R 3 OOC-A-CONR 4 R 6   (IIa),

wherein R 3 comprises a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually comprise a C 1 -C 36 alkyl group, wherein R 4 and R 5 can optionally together form a ring; and wherein A is a linear or a branched divalent C 2 -C 6 alkyl group;

at least one alkyldimethylamide;

ethyl levulinate;

at least one alkylene carbonate;

wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

9. The method of claim 8 ,

wherein N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the composition, wherein the dimethylsulfoxide is present in an amount of at least 39.7 wt %, by total weight of the liquid inhibitor composition.

10. The method of claim 9 , wherein N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the composition.

11. The method of claim 8 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide;

optionally the co-solvent; and

optionally, the dye.

12. The method of claim 8 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide;

optionally the water; and

optionally, the dye.

13. The method of claim 8 , wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide; and

optionally, the dye.

14. A concentrated liquid fertilizer composition comprising, based on 100 parts by weight of the composition:

(a) up to about 99 parts by weight of one or more nitrogenous fertilizer compounds,

(b) a liquid inhibitor composition that consists of N-(n-butyl)-thiophosphoric triamide dispersed in a liquid medium,

the liquid medium consists of:

at least one organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 1 -C 4 alkyl group,

and

(d) dimethylsulfoxide, and

optionally, at least one co-solvent selected from:

at least one dibasic ester selected from the group consisting of di(C 1 -C 12 )alkyl esters of saturated linear or branched (C2-C8)aliphatic dicarboxylic acids and mixtures thereof;

at least one compound of formula (IIa):

R 3 OOC-A-CONR 4 R 6   (IIa),

wherein R 3 comprises a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually comprise a C 1 -C 36 alkyl group, wherein R 4 and R 5 can optionally together form a ring; and wherein A is a linear or a branched divalent C 2 -C 6 alkyl group;

at least one alkyldimethylamide;

ethyl levulinate; or

at least one alkylene carbonate;

optionally fertilizer, wherein at least one said fertilizer is a nitrogenous fertilizer;

optionally water;

optionally at least one dye; and

wherein the alkyl thiophosphoric triamide is 30 to 60 wt %, by total weight of:

the alkyl thiophosphoric triamide or the mixture comprising the alkyl thiophosphoric triamide and the dicyandiamide,

the at least one organophosphate solvent,

the dimethylsulfoxide and, if present the co-solvent,

wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent, and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

15. The concentrated liquid fertilizer composition of claim 14 , wherein the organophosphate solvent is of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 2 -C 4 alkyl group, wherein N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the composition, wherein the dimethylsulfoxide is present in an amount of at least 39.7 wt %, by total weight of the liquid inhibitor composition.

16. The concentrated liquid fertilizer composition of claim 14 , wherein the inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide; and

optionally, the dye.

17. The concentrated liquid fertilizer composition of claim 14 ,

wherein there is up to about 99 parts by weight of the one or more nitrogenous fertilizer compounds,

wherein the liquid inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide,

the at least one organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 2 -C 4 alkyl group; and

the dimethylsulfoxide, wherein the dimethylsulfoxide is present in an amount of at least 39.7 wt %, by total weight of the liquid inhibitor composition,

wherein the N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the liquid inhibitor composition.

18. A method of making an aqueous end use fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with an inhibitor composition, the inhibitor composition consisting of:

N-(n-butyl)-thiophosphoric triamide dispersed in a liquid medium,

the liquid medium consisting of:

at least one organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 1 -C 4 alkyl group, and

dimethylsulfoxide;

optionally, dicyandiamide,

optionally, water;

optionally, a dye; and

optionally a co-solvent selected from the group consisting of

at least one dibasic ester selected from the group consisting of di(C1-C12)alkyl esters of saturated linear or branched (C2-C8)aliphatic dicarboxylic acids and mixtures thereof;

at least one compound of formula (IIa):

R 3 OOC-A-CONR 4 R 6   (IIa),

wherein R 3 comprises a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually comprise a C 1 -C 36 alkyl group, wherein R 4 and R 5 can optionally together form a ring; and wherein A is a linear or a branched divalent C 2 -C 6 alkyl group;

at least one alkyldimethylamide;

ethyl levulinate; and

at least one alkylene carbonate;

wherein the N-butyl thiophosphoric triamide is 30 to 60 wt %, by total weight of the inhibitor composition,

wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

19. The method of claim 18 , wherein the inhibitor composition consists of:

the N-(n-butyl)-thiophosphoric triamide;

the at least one organophosphate solvent;

the dimethylsulfoxide;

optionally, the dicyandiamide; and

optionally, the dye.

20. The method of claim 18 ,

wherein in the at least one solvent of formula (VIII):

R 1 , R 2 and R 3 , are each independently chosen from a C 2 -C 4 alkyl group,

wherein N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the inhibitor composition; and

wherein the dimethylsulfoxide is present in an amount of at least 39.7 wt %, by total weight of the inhibitor composition.

21. A liquid agricultural composition consisting of

inhibitor consisting of a N-butyl thiophosphoric triamide as a urease inhibitor and optionally dicyandiamide as a nitrification inhibitor;

an organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each independently chosen from a C 1 -C 2 alkyl group;

dimethylsulfoxide;

optionally, at least one co-solvent selected from:

at least one dibasic ester selected from the group consisting of di(C 1 -C 12 )alkyl esters of saturated linear or branched (C 2 -C 8 )aliphatic dicarboxylic acids and mixtures thereof;

at least one compound of formula (IIa):

R 3 OOC-A-CONR 4 R 5 (IIa),

wherein R 3 comprises a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually comprise a C 1 -C 36 alkyl group, wherein R 4 and R 5 can optionally together form a ring; and wherein A is a linear or a branched divalent C 2 -C 6 alkyl group;

at least one alkyldimethylamide;

ethyl levulinate; or

at least one alkylene carbonate;

optionally fertilizer, wherein at least one said fertilizer is a nitrogenous fertilizer;

optionally water;

optionally at least one dye; and

wherein the N-butyl thiophosphoric triamide is 30 to 60 wt %, by total weight of the inhibitor, organophosphate solvent, dimethylsulfoxide, and, if present, co-solvent,

wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

22. The composition of claim 21 , consisting of

N-butyl thiophosphoric triamide as the urease inhibitor;

the organophosphate solvent of formula (VIII):

wherein R 1 , R 2 and R 3 , are each selected from the C 1 -C 2 alkyl group;

the dimethylsulfoxide;

optionally the fertilizer, wherein at least one said fertilizer is a nitrogenous fertilizer;

optionally the water;

optionally the at least one dye, wherein N-butyl thiophosphoric triamide is present at greater than 45 and up to 55 wt %, by total weight of the composition.

23. The composition of claim 22 , wherein the N-butyl thiophosphoric triamide is 40 to 60 wt %, by total weight of the N-butyl thiophosphoric, the organophosphate solvent, and the dimethylsulfoxide.

24. The composition of claim 22 , wherein the N-butyl thiophosphoric triamide is 40 to 60 wt %, by total weight of the N-butyl thiophosphoric triamide , organophosphate solvent, dimethylsulfoxide, and, if present, co-solvent,

wherein the fertilizer, the water, and the at least one dye are present in the composition.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →