# US 10,501,384 B2 · Composition containing N-(n-butyl) thiophosphoric triamide adducts and reaction products > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,384 B2 - Document ID: US10501384B2 - Status: Granted - Kind: B2 - Application number: 15/875,748 - Filed: 2018-01-19 - Published: 2018-07-26 - Granted: 2019-12-10 - Earliest claimed: 2017-01-20 - Assignees: Koch Agronomic Services, LLC - Applicants: Koch Agronomic Services, LLC - Inventors: Douglas Barr; Ethel Garnier; Stanley Freeman - Web page: https://patentgrep.com/patent/US10501384B2 ## CPC - C05G 3/90: for affecting the nitrification of ammonium compounds or urea in the soil - C05C 9/00: Fertilisers containing urea or urea compounds - C07F 9/224: {Phosphorus triamides} - Y02P 60/21: Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures - C05G: MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS (organic fertilisers containing added bacterial cultures, mycelia, or the like C05F11/08; organic fertilisers containing plant vitamins or hormones C05F11/10); FERTILISERS CHARACTERISED BY THEIR FORM - C05C: NITROGENOUS FERTILISERS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## 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. ## Claims ### Claim 1 A composition comprising: an adduct of Formula A or Formula B: wherein R1 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 R2 and R3 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) The composition of claim 1, wherein R1 is H, OH, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, pentyl, iso-pentyl, phenyl, or 2-furyl. ### Claim 4 (depends on 1) The composition of claim 1, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 5 (depends on 1) The composition of claim 1, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 6 (depends on 1) The composition of claim 1, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 7 (depends on 1) The composition of claim 1, wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:2. ### Claim 8 (depends on 1) The composition of claim 1, wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:4. ### Claim 9 (depends on 1) The composition of claim 1, wherein the molar ratio of free NBPT:adduct is about 1:1 to about 1:6. ### Claim 10 A composition comprising: an adduct of Formula A or Formula B wherein R1 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 R2 and R3 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. ### Claim 11 (depends on 10) 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. ### Claim 12 (depends on 10) 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. ### Claim 13 (depends on 10) 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. ### Claim 14 (depends on 10) 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. ### Claim 15 (depends on 10) 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. ### Claim 16 (depends on 10) 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. ### Claim 17 (depends on 10) The composition of claim 10, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 18 (depends on 10) The composition of claim 10, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 19 A method for preparing a composition comprising: an adduct of Formula A or Formula B: wherein R1 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 R2 and R3 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 method 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. ### Claim 20 (depends on 19) The method of claim 19, 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. ### Claim 21 (depends on 19) The method of claim 19, 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. ### Claim 22 (depends on 19) The method of claim 19, 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. ### Claim 23 (depends on 19) The method of claim 19, wherein the reaction is carried out at a temperature ranging from about 25° C. to about 40° C. ### Claim 24 (depends on 19) The method of claim 19, wherein the reaction is carried out at a temperature ranging from about 25° C. to about 50° C. ### Claim 25 (depends on 19) The method of claim 19, wherein the reaction is carried out at a temperature ranging from about 25° C. to about 60° C. ### Claim 26 (depends on 19) The method of claim 19, wherein the adduct of Formula A comprises an adduct of the following formula: ### Claim 27 (depends on 19) The method of claim 19, wherein the adduct of Formula A comprises an adduct of the following formula: