IP Library Granted Patent US 11,795,119
Granted Patent B2
US 11,795,119 · App. 17/199,516 · Granted Oct 24, 2023

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
C05C9/00C05B7/00C05C1/00C05C9/02C05C11/00C05G3/90C05G5/23C07F9/224C09K15/12C09K15/18C09K15/28C09K15/324Y02P60/21
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Quick Facts
Patent No.
US 11,795,119
App. No.
17/199,516
Granted
Oct 24, 2023
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 (49)

1. A stable liquid agricultural composition comprising

N-(n-butyl)-thiophosphoric triamide (NBPT) urease inhibitor and dicyandiamide, wherein the NBPT and dicyandiamide are present at 5-75 wt. % of the composition;

dimethyl sulfoxide;

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, mint, oil Japanese cherry, or α-Ionone,

and

an amine stabilizer selected from the group consisting of 2-amino-2-methyl-1-propanol, amino-2-propanol, 2-amino-1-butanol and mixtures thereof,

wherein the amine stabilizer is present in an amount of from 1 wt % to about 15 wt %, by total weight of the composition, and

wherein there is an absence of each and every 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 and R 3 is not H.

2. The liquid agricultural composition of claim 1 , wherein at least 38 wt. % of the composition is dimethyl sulfoxide and the amine stabilizer is present in an amount of from 1 wt % to about 10 wt %, by weight of composition.

3. The liquid agricultural composition of claim 2 , wherein 38 to 49 wt. % of the composition is dimethyl sulfoxide.

4. The liquid agricultural composition of claim 3 , wherein the amine stabilizer is 2-amino-2-methyl-1-propanol, amino-2-propanol, or mixtures thereof.

5. The liquid agricultural composition of claim 4 , wherein the amine stabilizer is present in an amount of from 1 to 5 wt. % by total weight of the liquid agricultural composition.

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

7. The liquid agricultural composition of claim 1 , further comprising at least one dye.

8. A method of making a solid or concentrated liquid fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with a liquid agricultural composition of claim 1 .

9. A stable liquid agricultural composition comprising:

N-(n-butyl)-thiophosphoric triamide (NBPT) urease inhibitor and dicyandiamide, wherein the NBPT and dicyandiamide are present at 5-75 wt. % of the composition;

dimethyl sulfoxide;

an amine stabilizer selected from the group consisting of 2-amino-2-methyl-1-propanol, amino-2-propanol, 2-amino-1-butanol and mixtures thereof,

wherein the amine stabilizer is present in an amount of from 1 to 15 wt. %, by total weight of the composition;

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;

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

c) a glycol or glycol derivative; and

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, mint, oil Japanese cherry, or α-Ionone,

wherein there is an absence of each and every 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 and R 3 is not H.

10. The liquid agricultural composition of claim 9 , wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) urease inhibitor and dicyandiamide is present in an amount between 14 and 55 wt %, by total weight of composition.

11. The liquid agricultural composition of claim 10 , wherein 38 to 49 wt. % of the composition is dimethylsulfoxide.

12. The liquid agricultural composition of claim 9 , wherein the composition contains 10 to 75% total urease inhibitor and nitrification inhibitor.

13. The liquid agricultural composition of claim 9 wherein the amine stabilizer is 2-amino-2-methyl-1-propanol, amino-2-propanol or mixtures thereof present in an amount of from 1 wt % to about 5 wt %, by weight of composition.

14. The liquid agricultural composition of claim 9 , wherein the amine stabilizer is present in an amount of from 1 to 5 wt. % by total weight of the liquid agricultural composition.

15. A stable liquid agricultural composition consisting of:

N-(n-butyl)-thiophosphoric triamide (NBPT) urease inhibitor and dicyandiamide, wherein the NBPT and dicyandiamide are present at 5-75 wt. % of the composition;

dimethyl sulfoxide, wherein at least 38 wt. % of the composition is dimethyl sulfoxide;

an amine stabilizer selected from the group consisting of 2-amino-2-methyl-1-propanol, amino-2-propanol, 2-amino-1-butanol and mixtures thereof, wherein the amine stabilizer is present in an amount of from 1 wt % to 15 wt %, by weight of composition;

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 one or more selected from the group consisting of a hydrogen, an alkyl group, an alkenyl group, and a phenyl group, wherein n is an integer of from 1 to 10;

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 one or more selected from the group consisting of a linear and a branched divalent C 2 -C 12 alkyl group; and

c) one or more selected from the group consisting of a glycol, and glycol derivative; and

optionally, at least one dye;

at least one odor masking agent selected from the group consisting of terpineol, 4-allylanisole, limonene4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate, benzaldehyde, diethyl malonate, cyclohexyl acetate, mint, oil Japanese cherry, and α-Ionone.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
NUNC PRO TUNC ASSIGNMENT Recorded Dec 22, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066098/0077 →