IP Library Granted Patent US 10,934,228
Granted Patent B2
US 10,934,228 · App. 16/534,473 · Granted Mar 2, 2021

High temperature amine-stabilized DCD and/or alkyl thiophosphoric triamide solvent systems and use in agricultural applications

Inventors: Marivi Ortiz-Suarez (Burlington, NJ); James Sawyer (Yardley, PA); Christopher Harris (Worcester, GB)
Assignee: RHODIA OPERATIONS
C05G3/90C05C9/00C05C11/00C05G5/20C09K15/18Y02P60/21
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Quick Facts
Patent No.
US 10,934,228
App. No.
16/534,473
Granted
Mar 2, 2021
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 and at least one amine stabilizer, is useful in making fertilizer compositions and in a method of fertilizing target plants.

Claims (86)

1. A high temperature stable liquid agricultural composition comprising:

45 wt. % to 55 wt. % of N-(n-butyl)-thiophosphoric triamide (NBPT);

dimethylsulfoxide;

1 wt. % to 5 wt. % of a stabilizer consisting of (methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, and

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

(a) at least one dioxolane compound of formula (I.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;

b) at least one dibasic ester;

c) 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 6 alkyl group;

d) at least one alkyldimethylamide;

e) at least one alkyl lactate;

f) ethyl levulinate;

g) at least one alkyoxyalcohol, ether alcohol, or alcohol;

h) at least one glycerine or glycerine derivative;

i) at least one alkylene carbonate; and

j) organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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; and

wherein the wt. % are based on a total weight of the composition.

2. The liquid agricultural composition of claim 1 , wherein the stable liquid agricultural composition consists of

45 wt. % to 55 wt % of the N-(n-butyl)-thiophosphoric triamide (NBPT), and

at least 2 wt. % to less than 3 wt. % of the stabilizer consisting of the (methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, and optionally the at least one solvent, wherein the wt. % are based on a total weight of the composition; and

the dimethylsulfoxide.

3. The liquid agricultural composition of claim 1 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount between 45 wt. % and less than about 50 wt. %, based on a total weight of the composition.

4. The liquid agricultural composition of claim 1 , wherein the stabilizer is present in an amount between 1 wt. % and 3 wt. % based on a total weight of the composition.

5. The liquid agricultural composition of claim 1 , wherein the at least one solvent is present and comprises the organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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.

6. A method of stabilizing a liquid fertilizer composition at high temperatures comprising contacting one or more nitrogenous fertilizer compounds with the high temperature stable liquid agricultural composition of claim 1 .

7. The method of claim 6 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) is present in an amount between 45 and 50 wt. % by weight of the liquid inhibitor composition.

8. 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, and

(b) the high temperature stable liquid agricultural composition of claim 1 .

9. The concentrated liquid fertilizer composition of claim 8 , wherein the at least one said solvent is:

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.

10. The concentrated liquid fertilizer composition of claim 8 , wherein the at least one said solvent is:

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

organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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.

11. The concentrated liquid fertilizer composition of claim 8 , wherein the at least one said solvent is organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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.

12. A high temperature stable liquid agricultural composition comprising:

45 wt. % to 55 wt. % of N-(n-butyl)-thiophosphoric triamide (NBPT);

1 wt. % to 5 wt. % of a stabilizer consisting of (methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, and

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

(a) at least one dioxolane compound of formula (I.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;

b) at least one dibasic ester;

c) 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 6 alkyl group;

d) at least one alkyldimethylamide;

e) at least one alkyl lactate;

f) ethyl levulinate;

g) at least one alkyoxyalcohol, ether alcohol, or alcohol;

h) at least one glycerine or glycerine derivative;

i) at least one alkylene carbonate; and

j) organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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; and

wherein the wt. % are based on a total weight of the composition,

and no dimethylsulfoxide is present in the composition.

13. The liquid agricultural composition of claim 12 , wherein the stable liquid agricultural composition consists of:

45 wt. % to 55 wt % of N-(n-butyl)-thiophosphoric triamide (NBPT),

2 wt. % to less than 3 wt. % of the stabilizer;

and

the at least one solvent.

14. The liquid agricultural composition of claim 13 , wherein the at least one solvent is present and consists of at least one dioxolane compound of formula (II.b):

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

15. A method of stabilizing a liquid fertilizer composition at high temperatures comprising contacting one or more nitrogenous fertilizer compounds with the high temperature stable liquid agricultural composition of claim 12 .

16. The method of claim 15 , wherein the stabilizer is present at least 2 to less than 3 wt. %.

17. The method of claim 15 , wherein the stabilizer is present in an amount between 1 wt. % and 3 wt. %.

18. The method of claim 15 , wherein the stabilizer is present in an amount between 2 wt. % and 3 wt. %.

19. A method of making a solid or concentrated liquid fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with the high temperature stable liquid agricultural composition of claim 1 .

20. The method of claim 19 , wherein the solvent comprises at least one member of the group consisting of:

organophosphate of formula (I.a):

wherein R 1 , R 2 and R 3 , are each independently chosen from 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 and

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.

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

45 wt. % to 55 wt. % of the N-(n-butyl)-thiophosphoric triamide (NBPT), and at least 2 wt. % to less than 3 wt. % of the stabilizer.

22. A high temperature stable liquid agricultural composition consisting of:

at least one urease inhibitor, wherein the urease inhibitor is N-(n-butyl)-thiophosphoric triamide (NBPT);

dimethylsulfoxide; and

at least one stabilizer, wherein said stabilizer is 2-(2-aminoethoxy) ethanol.

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 →