IP Library Granted Patent US 10,556,836
Granted Patent B2
US 10,556,836 · App. 16/207,352 · Granted Feb 11, 2020

Solvent systems of N-alkyl thiophosphoric triamides and methods of use in agricultural applications

Inventors: Leahann Iannotta (Wayne, PA); Rajesh Pazhianur (Belle Mead, NJ); Krish Murthy Shanmuga (Plainsboro, NJ); John A. Latting (Bluffton, SC); T. Kent Woodall (Kearney, MO)
Assignees: RHODIA OPERATIONS; ROSEN'S INC.
C05B15/00C05G3/08
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Quick Facts
Patent No.
US 10,556,836
App. No.
16/207,352
Granted
Feb 11, 2020
Kind
B2
Abstract

Solvent systems for the formulation of alkyl thiophosphoric triamide urease inhibitors, that provide stable dispersion of alkyl thiophosphoric triamides for even distribution (in low or high concentrations) onto fertilizers containing urea in liquid or solid form.

Claims (50)

1. A composition comprising:

a) at least one alkyl thiophosphoric triamide as a urease inhibitor, wherein the alkyl thiophosphoric triamide is present in an amount between 15% by weight of the composition and 35% by weight of the composition;

b) a solvent comprising at least one dioxolane compound of formula (Ia):

wherein R 6 and R 7 individually comprises an alkyl group, an alkenyl group, or a phenyl group, wherein n is an integer of from 1 to 10, wherein the dioxolane compound is present in an amount from at least 25% by weight of the composition;

wherein the composition is free of amide solvent.

2. The composition of claim 1 ,

wherein the dioxolane compound is present in an amount from 25% by weight of the composition to 70% by weight of the composition,

optionally further comprising a co-solvent selected from the group consisting of:

at least one dibasic ester;

at least one alkyl lactate;

ethyl levulinate;

at least one alkyoxyalcohol, ether alcohol, amine alcohol, amino alcohol or alcohol;

at least one glycerine or glycerine derivative;

at least one alkylene carbonate;

ketones;

aliphatic or acyclic hydrocarbon solvents;

halogenated solvents;

aromatic hydrocarbon solvents;

cyclic terpenes;

unsaturated hydrocarbon solvents;

halocarbon solvents; and

any combination thereof.

3. The composition of claim 2 , comprising the at least one dibasic ester, wherein the at least one dibasic ester comprises at least two of: dialkyl methylglutarate, dialkyl ethylsuccinate, dialkyl adipate, dialkyl succinate or dialkyl glutarate.

4. The composition of claim 2 , comprising the at least one dibasic ester, wherein the at least one dibasic ester comprises a blend of dialkyl methylglutarate, dialkyl ethylsuccinate and, optionally, dialkyl adipate.

5. The composition of claim 2 , comprising the at least one dibasic ester, wherein the at least one dibasic ester comprises a blend of dialkyl adipate, dialkyl succinate and dialkyl glutarate.

6. The composition of claim 2 , comprising the alkyl lactate, wherein the alkyl lactate is a C 1 -C 8 alkyl lactate.

7. The composition of claim 2 , comprising the alkoxyalcohol, wherein the alkoxyalcohol is 2-butoxyethanol.

8. The composition of claim 2 , comprising the alkylene carbonate, wherein the at least one alkylene carbonate is propylene carbonate.

9. The composition of claim 2 , comprising the amine alcohol, wherein the amine alcohol is selected from the group consisting of ethanolamine, propanolamine, dialkyl alkanolamines, methanolamine, and any combination thereof.

10. The composition of claim 1 , wherein n is an integer of from 1 to 4 and R 6 and R 7 individually comprises an alkyl group, and the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide.

11. The composition of claim 1 , wherein n is an integer of from 1 to 2 and R 6 and R 7 are each selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, and isobutyl and the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide and present in an amount between 15% by weight of the composition and 26.25% by weight of the composition.

12. The composition of claim 1 , wherein n is 1 and R 6 and R 7 are each methyl, wherein the dioxolane compound is present in an amount from 25% to 70% by weight of the composition, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide and present in an amount between 20% by weight of the composition and 30% by weight of the composition.

13. The composition of claim 1 ,

wherein the dioxolane compound is present in an amount from 54.65% by weight of the composition to 70% by weight of the composition; and

wherein there is an absence of amide surfactant.

14. The composition of claim 1 , wherein the composition is a flowable liquid composition.

15. The composition of claim 14 , wherein the flowable liquid composition is a homogenous solution.

16. The composition of claim 14 , wherein the flowable liquid composition is a mixture.

17. The composition of claim 1 , wherein the alkyl thiophosphoric triamide is present in an amount between 20% and 35% by weight of the composition.

18. The composition of claim 1 , wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide and present in an amount between 26.25% and 35% by weight of the composition.

19. The composition of claim 1 , wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide and present in the dispersion in an amount between 30% by weight of the dispersion and 35% by weight of the composition.

20. The composition of claim 1 , further comprises at least one dibasic ester blend comprising:

(i) a first dibasic ester of formula:

(ii) a second dibasic ester of formula:

and

(iii) optionally, a third dibasic ester of formula:

wherein R 1 and R 2 individually comprise a C 1 -C 8 alkyl group.

21. A method for preparing an agricultural composition comprising contacting the composition of claim 1 with a nitrogen-based fertilizer composition.

22. The method of claim 21 , wherein the nitrogen-based fertilizer composition is in granular form.

23. The method of claim 21 , wherein the nitrogen-based fertilizer composition is in substantially liquid form.

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 →