Composition containing N-(n-butyl) thiophosphoric triamide adducts and reaction products

Patent metadata

Field	Value
Publication number	US-10501384-B2
Application number	US-201815875748-A
Country	US
Kind code	B2
Filing date	Jan 19, 2018
Priority date	Jan 20, 2017
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

Reaction products and methods for making and using such reaction products are provided. For example, a reaction product comprising an adduct formed from two or more of a first nucleophile (e.g., including, but not limited to, a urease inhibitor), a second nucleophile, and an electrophile is described, which can be provided in various forms. Such a reaction product can be in the form of a solid or solution. Such a reaction product can also be combined with one or more additional components, including but not limited to, free urease inhibitor and/or a nitrogen-based fertilizer composition.

First claim

The invention claimed is:

1. A composition comprising:
an adduct of Formula A or Formula B:

wherein R 1 is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted heteroalkyl group, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl;
n is 0, 1, 2, or 3; and
R 2 and R 3 are each independently a nucleophile, which is a nitrification inhibitor, a urease inhibitor, or urea;
free N-(n-butyl)thiophosphoric triamide (NBPT); and
an organic solvent selected from glycols, glycol derivatives and protected glycols,
acetonitrile, DMSO, alkanolamines, alkylsulfones, alkyl amides, monoalcohols, dibasic esters and derivatives thereof, alkylene carbonates, monobasic esters, carboxylic acids, glycol esters, surfactants, and combinations thereof;
wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:10.

2. The composition of claim 1 , wherein the nucleophile is urea, N-(n-butyl)thiophosphoric triamide (NBPT), 2-chloro-6-trichloromethyl-pyridine, 5-ethoxy-3-trichloromethyl-1, 2, 4-thiadiazol, dicyandiamide (DCD), 4-amino-1,2,4-triazole, 3,5-2 dimethylpyrazole, 2-amino-4-chloro-6-methyl-pyrimidine, 1,3-benzothiazole-2-thiol, 4-amino-N-1,3-thiazol-2-ylbenzenesulfonamide, thiourea, guanidine, 3,4-dimethylpyrazole phosphate, 3,5-dimethyl pyrazole, 2, 4-diamino-6-trichloromethyl-5-triazine, polyetherionophores, 4-amino-1,2, 4-triazole, 3-mercapto-1,2,4-triazole, potassium azide, carbon bisulfide, sodium trithiocarbonate, ammonium dithiocarbamate, 2,3, dihydro-2,2-dimethyl-7-benzofuranol methyl-carbamate, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester, ammonium thiosulfate, 1-hydroxypyrazole, 2-methylpyrazole-1-carboxamide, or a combination thereof.

3. The composition of claim 1 , wherein R 1 is H, OH, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, pentyl, iso-pentyl, phenyl, or 2-furyl.

4. The composition of claim 1 , wherein the adduct of Formula A comprises an adduct of the following formula:

5. The composition of claim 1 , wherein the adduct of Formula A comprises an adduct of the following formula:

6. The composition of claim 1 , wherein the adduct of Formula A comprises an adduct of the following formula:

7. The composition of claim 1 , wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:2.

8. The composition of claim 1 , wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:4.

9. The composition of claim 1 , wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:6.

10. A composition comprising:
an adduct of Formula A or Formula B

wherein R 1 is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted heteroalkyl group, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl;
n is 0, 1, 2, or 3; and
R 2 and R 3 are each independently a nucleophile, which is a nitrification inhibitor, a urease inhibitor, or urea;
free N-(n-butyl)thiophosphoric triamide (NBPT); and
an organic solvent selected from the group consisting of glycols, glycol derivatives, protected glycols, glycol ethers, acetonitrile, DMSO, alkanolamines, alkylsulfones, alkyl amides, monoalcohols, dibasic esters and derivatives thereof, alkylene carbonates, monobasic esters, carboxylic acids, glycol esters, surfactants, and combinations thereof;
the composition prepared by a process comprising:
(a) providing a solution of N-(n-butyl)thiophosphoric triamide (NBPT), in the organic solvent, optionally comprising an aqueous solvent;
(b) adding a nucleophile;
(c) adding an electrophile;
(d) reacting the resulting mixture at a temperature ranging from about 25° C. to about 70° C.; and
(e) cooling the mixture to room temperature, wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:10.

11. The composition prepared by the process of claim 10 , wherein the organic solvent is an N-alkyl 2-pyrrolidone, glycerol, isopropylidine glycerol, ethyl acetate, acetonitrile, DMSO, propylene glycol, benzyl alcohol, or a combination thereof.

12. The composition prepared by the process of claim 10 , wherein the nucleophile is urea, N-(n-butyl)thiophosphoric triamide (NBPT), 2-chloro-6-trichloromethyl-pyridine, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazol, dicyandiamide (DCD), 4-amino-1,2,4-triazole, 3,5-dimethylpyrazole, 2-amino-4-chloro-6-methyl-pyrimidine, 1,3-benzothiazole-2-thiol, 4-amino-N-1,3-thiazol-2-ylbenzenesulfonamide, thiourea, guanidine, 3,4-dimethylpyrazole phosphate, 3,5-dimethylpyrazole, 2,4-diamino-6-trichloromethyl-5-triazine, polyetherionophores, 4-amino-1,2,4-triazole, 3-mercapto-1,2,4-triazole, potassium azide, carbon bisulfide, sodium trithiocarbonate, ammonium dithiocarbamate, 2,3, dihydro-2,2-dimethyl-7-benzofuranol methyl-carbamate, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester, ammonium thiosulfate, 1-hydroxypyrazole, 2-methylpyrazole-1-carboxamide, or a combination thereof.

13. The composition prepared by the process of claim 10 , wherein the electrophile is formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, 2-methyl butanal, 2-ethyl butanal, pentanal, benzaldehyde, furfural, glyoxal, malondialdehyde, succindialdehyde, glutaraldehyde, or a combination thereof.

14. The composition prepared by the process of claim 10 , wherein the reaction is carried out at a temperature ranging from about 25° C. to about 40° C.

15. The composition prepared by the process of claim 10 , wherein the reaction is carried out at a temperature ranging from about 25° C. to about 50° C.

16. The composition prepared by the process of claim 10 , wherein the reaction is carried out at a temperature ranging from about 25° C. to about 60° C.

17. The composition of claim 10 , wherein the adduct of Formula A comprises an adduct of the following formula:

18. The composition of claim 10 , wherein the adduct of Formula A comprises an adduct of the following formula:

19. A method for preparing a composition comprising:
an adduct of Formula A or Formula B:

wherein R 1 is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted heteroalkyl group, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl;
n is 0, 1, 2, or 3; and
R 2 and R 3 are each independently a nucl

Assignees

• Koch Agronomic Services Llc

Inventors

• Barr Douglas
• Garnier Ethel
• Freeman Stanley

Classifications

• C05C9/00 Primary

  Fertilisers containing urea or urea compounds · CPC title

• C05G3/90 Primary

  for affecting the nitrification of ammonium compounds or urea in the soil · CPC title

• C07F9/224

  Phosphorus triamides · CPC title

• Y02P60/218

  Cross-Sectional Technologies · mapped topic

• C05G3/08 Primary

  Chemistry & Metallurgy · mapped topic