IP Library Granted Patent US 10,173,935
Granted Patent B2
US 10,173,935 · App. 13/711,768 · Granted Jan 8, 2019

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

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Quick Facts
Patent No.
US 10,173,935
App. No.
13/711,768
Granted
Jan 8, 2019
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 (68)

1. A composition comprising:

at least one alkyl thiophosphoric triamide, wherein the alkyl thiophosphoric triamide is present in an amount between 15% by weight of the composition and 35% by weight of the composition dispersed into a carrier;

solvent of said carrier consisting of at least one dioxolane compound of formula (Ia):

wherein R 6 and R 7 individually comprises an alkyl group, wherein n is an integer of from 1 to 4 , and optional co-solvent;

wherein the dioxolane compound is present in an amount from at least 25% by weight of the composition; and

wherein the optional co-solvent is 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; and

any combination thereof.

2. 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.

3. The composition of claim 2 , wherein n is 1 and R 6 and R 7 are each methyl, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide.

4. 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, wherein the alkyl thiophosphoric triamide is present in an amount between about 15% by weight of the composition and about 30% by weight of the composition.

5. The composition of claim 4 ,

wherein the dioxolane compound is present in an amount from 54.65% by weight of the composition to 70% by weight of the composition, wherein n is 1 and R 6 and R 7 are each methyl.

6. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the at least one alcohol.

7. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the at least one dibasic ester, wherein the at least one dibasic ester consists of at least two dibasic esters selected from the group consisting of: dialkyl methylglutarate, dialkyl ethylsuccinate, dialkyl adipate, dialkyl succinate and dialkyl glutarate.

8. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the at least one dibasic ester, wherein the at least one dibasic ester consists of a blend of dialkyl methylglutarate, dialkyl ethylsuccinate and, optionally, dialkyl adipate.

9. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the at least one dibasic ester, wherein the at least one dibasic ester consists of a blend of dialkyl adipate, dialkyl succinate and dialkyl glutarate.

10. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the alkyl lactate, wherein the alkyl lactate is a C 1 -C 8 alkyl lactate.

11. The composition of claim 1 , wherein the co-solvent is present in the composition and consists of the alkoxyalcohol, wherein the alkoxyalcohol is 2-butoxyethanol.

12. The composition of claim 1 , wherein the co-solvent is the present in the composition and consists of the alkylene carbonate, wherein the at least one alkylene carbonate is propylene carbonate.

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

14. The composition of claim 13 , wherein the flowable liquid composition is a homogenous solution.

15. The composition of claim 13 , wherein the flowable liquid composition is a mixture, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide.

16. The composition of claim 1 , wherein the amine alcohol is present in the composition, wherein the amine alcohol is selected from the group consisting of ethanolamine, propanolamine, dialkyl alkanolamines, methanolamine, and any combination thereof.

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

18. The method of claim 17 , wherein the nitrogen-based fertilizer composition is in granular form.

19. The method of claim 17 , wherein the nitrogen-based fertilizer composition is in substantially liquid form.

20. A composition consisting of:

a) alkyl thiophosphoric triamide, wherein the alkyl thiophosphoric triamide is present in an amount between 15% by weight of the composition and 35% by weight of the composition, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide;

b) a solvent selected from the group consisting of at least one dioxolane compound of formula (Ia):

wherein R 6 and R 7 individually are an alkyl group, wherein n is an integer of from 1 to 4; and

c) optionally 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; and

any combination thereof;

d) optionally a dye;

e) optionally a surfactant.

21. The composition of claim 20 , comprising alkyl thiophosphoric triamide in the amount of 15 w % to 35 w % wherein the dioxolane compound is present in an amount from at least 25% by weight of the composition.

22. The composition of claim 20 , consisting of:

a) the alkyl thiophosphoric triamide;

b) the solvent;

c) optionally the co-solvent; and

d) optionally the dye.

23. The composition of claim 22 , comprising alkyl thiophosphoric triamide in the amount of 15 w % to 35 w % wherein the dioxolane compound is present in an amount of at least 25% by weight of the composition.

24. The composition of claim 22 , wherein the dioxolane compound is present in an amount from 25% to 70% by weight of the composition.

25. The composition of claim 21 , consisting of:

wherein the alkyl thiophosphoric triamide is present in an amount between 21% by weight of the composition and 26.6% by weight of the composition, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide;

wherein the co-solvent is present and selected from the group consisting of at least one ethyl lactate, at least one dibasic ester, at least one alcohol, and any combination thereof.

26. The composition of claim 25 , wherein the co-solvent is present and selected from the group consisting of at least one alcohol.

27. The composition of claim 26 , comprising alkyl thiophosphoric triamide in the amount of 15 w % to 35 w % wherein the dioxolane compound is present in an amount from at least 25% by weight of the composition.

28. The composition of claim 26 , wherein the dioxolane compound is present in an amount from 25% to 70% by weight of the composition.

29. A composition, consisting of:

a) alkyl thiophosphoric triamide, wherein the alkyl thiophosphoric triamide is present in an amount between 15% by weight of the composition and 30% by weight of the composition, wherein the alkyl thiophosphoric triamide is N-(n-butyl)-thiophosphoric triamide;

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

wherein R 6 and R 7 individually comprises an alkyl group, wherein n is an integer of from 1 to 4,

d) optionally, a dye.

30. The composition of claim 29 , comprising alkyl thiophosphoric triamide in the amount of 15 w % to 35 w % wherein the dioxolane compound is present in an amount from at least 25% by weight of the composition.

31. The composition of claim 29 , wherein the dioxolane compound is present in an amount from 25% by weight of the composition to 70% by weight of the composition.

32. The composition of claim 31 , wherein n is 1 and R 6 and R 7 are each methyl.

Assignments (7)
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 →
MERGER Recorded Nov 29, 2018
From: MIDTECH R&D, INC.
To: ROSEN'S INC.
Reel/Frame 048173/0979 →
MERGER AND CHANGE OF NAME Recorded Nov 8, 2018
From: MIDTECH R&D, INC.; ROSEN'S INC.
To: ROSEN'S INC.
Reel/Frame 048099/0262 →
RELEASE Recorded Dec 22, 2017
From: BANK OF MONTREAL, AS ADMINISTRATIVE AGENT
To: MIDTECH R&D, INC.
Reel/Frame 044921/0012 →
SECURITY INTEREST Recorded Jul 7, 2014
From: MIDTECH R&D, INC.
To: BANK OF MONTREAL, AS AGENT
Reel/Frame 033278/0891 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2013
From: IANNOTTA, LEAHANN; PAZHIANUR, RAJESH; SHANMUGA, KRISH MURTHY; LATTING, JOHN A.; WOODALL, T. KENT
To: RHODIA OPERATIONS; MIDTECH R&D, INC.
Reel/Frame 029763/0228 →