IP Library Granted Patent US 10,570,068
Granted Patent B2
US 10,570,068 · App. 16/207,824 · Granted Feb 25, 2020

Stabilized DCD and/or alkyl thiophosphoric triamide solvent systems and use in agricultural applications

Inventors: Hong Liu (Pennington, NJ); Jiamin Wu (Penndel, PA); Andre Gomes (Jackson, NJ); Krish Shanmuga (Plainsboro, NJ); Zhiyun Chen (Newtown, PA)
Assignee: RHODIA OPERATIONS
C05G3/08C05B7/00C05C1/00C05C9/00C05C11/00C05G3/0064C07F9/224C09K15/12C09K15/18C09K15/28C09K15/324Y02P60/218
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Quick Facts
Patent No.
US 10,570,068
App. No.
16/207,824
Granted
Feb 25, 2020
Kind
B2
Abstract

An inhibitor composition contains alkyl thiophosphoric triamide (or a mixture of alkyl thiophosphoric triamide and dicyandiamide),dissolved in a liquid medium comprising at least one organic solvent, at least one amine stabilizer and, optionally, at least one dye and/or at least one odor masking agent, is useful in making fertilizer compositions and in a method of fertilizing target plants.

Claims (82)

1. A stable liquid agricultural composition comprising

N-(n-butyl)-thiophosphoric triamide (NBPT) as a urease inhibitor, wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 14 to 35 wt %, by total weight of the composition;

a solvent blend comprising a mixture of triethylene glycol and propylene glycol;

optionally, dimethyl sulfoxide;

optionally, at least one nitrification inhibitor;

optionally, at least one co-solvent selected from the group consisting of:

(a) at least one dioxolane compound of formula (II.b):

wherein R 6 and R 7 individually comprises a hydrogen, an alkyl group, an alkenyl group, or a phenyl group, wherein n is an integer of from 1 to 10; and

(b) at least one compound of formula (III):

R 3 OOC-A-CONR 4 R 5   (III),

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 12 alkyl group; and

optionally, an amine stabilizer according to formula (IV):

wherein R 1 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 2 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 3 is H, CH 3 or a branched or linear

C 2 -C 5 alkyl group; and R 4 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group,

wherein the composition comprises at least 60 wt. % organic solvent comprising the solvent blend, optionally dimethylsulfoxide, and optionally co-solvent.

2. The liquid agricultural composition of claim 1 , further comprising at least one nitrification inhibitor.

3. The liquid agricultural composition of claim 2 , wherein the nitrification inhibitor is dicyandiamide (DCD).

4. The liquid agricultural composition of claim 1 , further comprising at least one dye wherein N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 14 to 30 wt %, by total weight of the composition.

5. The liquid agricultural composition of claim 1 , further comprising an odor masking agent comprising at least one of terpineol, 4-allylanisole, limonene4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate, benzaldehyde, diethyl malonate, cyclohexyl acetate, anisole, mint, oil Japanese cherry, or α-Ionone.

6. The liquid agricultural composition of claim 1 , having an absence of

co-solvent which is the at least one compound according to formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from H, a C 1 -C 16 alkyl group, a C 1 -C 16 alkenyl, group, a C 1 -C 16 alkoxyalkyl group, a C 7 -C 30 alkylarylalkyl group, a C 7 -C 30 arylalkyl group, or an aryl group, provided that at least one of R 1 , R 2 or R 3 is not H.

7. The liquid agricultural composition of claim 1 ,

comprising:

the urease inhibitor;

the dimethyl sulfoxide;

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

(a) at least one dioxolane compound of formula (II.b):

wherein R 6 and R 7 individually comprises a hydrogen, an alkyl group, an alkenyl group, or a phenyl group, wherein n is an integer of from 1 to 10; or

b) at least one compound of formula (III):

R 3 OOC-A-CONR 4 R 5   (III),

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 12 alkyl group; and

further comprising an odor masking agent comprising at least one of terpineol, 4-allylanisole, limonene4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate, benzaldehyde, diethyl malonate, cyclohexyl acetate, anisole, mint, oil Japanese cherry, or α-Ionone.

8. The liquid agricultural composition of claim 1 , wherein the organic solvent consists of the solvent blend.

9. The liquid agricultural composition of claim 1 , further comprising an amine stabilizer according to formula (IV):

wherein R 1 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 2 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 3 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group; and R 4 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group.

10. The liquid agricultural composition of claim 9 , wherein the amine stabilizer is 2-amino-2-methyl-1-propanol, amino-2-propanol, 2-amino-1-butanol or mixtures thereof.

11. The liquid agricultural composition of claim 1 , wherein N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 30 wt %, by total weight of the composition.

12. The liquid agricultural composition of claim 1 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 25 wt %, by total weight of the composition.

13. The liquid agricultural composition of claim 8 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 30 wt %, by total weight of the composition.

14. The liquid agricultural composition of claim 8 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 25 wt %, by total weight of the composition.

15. The liquid agricultural composition of claim 1 , comprising 60 to 80 wt. % organic solvent comprising the solvent blend, optionally dimethylsulfoxide, and optionally co-solvent.

16. The liquid agricultural composition of claim 9 , wherein the amine stabilizer is present in an amount less than 4% by total weight of the liquid fertilizer composition.

17. A method of making a solid or concentrated liquid fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with a liquid inhibitor composition of claim 1 that comprises N-(n-butyl)-thiophosphoric triamide (NBPT) as a urease inhibitor, wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 14 to 35 wt %, by total weight of the composition, which is dissolved or dispersed in a liquid medium comprising:

the solvent blend comprising a mixture of triethylene glycol and propylene glycol;

wherein the composition comprises at least 60 wt. % organic solvent comprising the solvent blend, optionally dimethylsulfoxide, and optionally co-solvent.

18. The method of claim 17 , wherein the liquid medium further comprises an odor masking agent comprising at least one of terpineol, 4-allylanisole, limonene4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate, benzaldehyde, diethyl malonate, cyclohexyl acetate, anisole, mint, oil Japanese cherry, or α-Ionone.

19. A stable liquid agricultural composition comprising, by weight of composition:

N-(n-butyl)-thiophosphoric triamide (NBPT) as a urease inhibitor, wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 14 to 35 wt %, by total weight of the composition;

a solvent blend comprising a mixture of triethylene glycol and propylene glycol;

optionally, at most 5 wt. % dye; and

optionally, less than 5 wt. % odor masking agent,

comprising at least 60 wt. % organic solvent comprising the solvent blend, optionally dimethylsulfoxide, and optionally co-solvent.

20. The liquid agricultural composition of claim 19 , wherein the-composition comprises greater than 25 to less than 30 wt % said urease inhibitor.

21. The liquid agricultural composition of claim 20 , comprising at least 60 wt. % said triethylene glycol and propylene glycol; and optionally, an amine stabilizer according to formula (IV):

wherein R 1 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 2 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 3 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group; and R 4 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group.

22. A stable liquid agricultural composition consisting of

N-(n-butyl)-thiophosphoric triamide (NBPT) as a urease inhibitor, wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 14 to 35 wt %, by total weight of the composition;

a solvent blend of triethylene glycol and propylene glycol;

optionally, at least one nitrification inhibitor;

optionally, at least one co-solvent selected from the group consisting of:

(a) at least one dioxolane compound of formula (II.b):

wherein R 6 and R 7 individually comprises a hydrogen, an alkyl group, an alkenyl group, or a phenyl group, wherein n is an integer of from 1 to 10; and

(b) at least one compound of formula (III):

R 3 OOC-A-CONR 4 R 5   (III),

wherein R 3 is a C 1 -C 36 alkyl group; wherein R 4 and R 5 individually are 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 12 alkyl group; and

optionally, an amine stabilizer according to formula (IV):

wherein R 1 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 2 is H, CH 3 , CH 2 CH 3 , or a branched or linear C 2 -C 5 alkyl group; R 3 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group; and R 4 is H, CH 3 or a branched or linear C 2 -C 5 alkyl group;

optionally, at most 5 wt. % dye; and

optionally, less than 5 wt. % odor masking agent,

wherein at least 60 wt. % of the composition is organic solvent which is the total of the solvent blend, and co-solvent.

23. The stable liquid agricultural composition of claim 22 , consisting of, by weight of composition:

14 to 35 wt % N-(n-butyl)-thiophosphoric triamide (NBPT);

the solvent blend consisting of triethylene glycol and propylene glycol;

optionally, at most 5 wt. % said dye; and

optionally, less than 5 wt. % said odor masking agent.

24. The liquid agricultural composition of claim 23 ,

wherein the dye is at most 1 wt. % of the composition and;

wherein the odor masking agent is less than 1.6 wt. % of the composition.

25. The liquid agricultural composition of claim 23 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 30 wt %, by total weight of the composition.

26. The liquid agricultural composition of claim 23 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount of 20 to 25 wt %, by total weight of 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 →
Continuity (3)
Continuation 15637110 · Jun 29, 2017
Provisional Application 62356035 · Jun 29, 2016
Related Publication 20190100472A1 · Apr 4, 2019