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

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.

1 . A composition, comprising an adduct of Formula 5, Formula 6, or Formula 7: 
       
         
           
           
               
               
           
         
       
       or mixtures thereof,
 wherein R 1  is a H, OH, 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 or 1; and 
 R 2  and R 3  are each independently a nucleophile, which is a nitrification inhibitor, a urease inhibitor, or urea. 
 
     
     
         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-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 the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The composition of  claim 1 , wherein the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The composition of  claim 1 , wherein the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The composition of  claim 1 , wherein the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         7 . The composition of  claim 1 , wherein the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         8 . The composition of  claim 1 , wherein the adduct of Formula 5 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The composition of  claim 1 , wherein the adduct of Formula 6 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The composition of  claim 1 , wherein the adduct of Formula 7 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The composition of  claim 1 , wherein the adduct of Formula 7 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         12 . The composition of  claim 1 , wherein the adduct of Formula 7 is an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         13 . The composition of  claim 1 , wherein the composition further comprises free N-(n-butyl)thiophosphoric triamide (NBPT). 
     
     
         14 . The composition of  claim 1 , wherein the composition further comprises an organic solvent selected from the group consisting of 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. 
     
     
         15 . The composition of  claim 14 , wherein the organic solvent is selected from the group consisting of N-alkyl 2-pyrrolidone, glycerol, isopropylidine glycerol, ethyl acetate, acetonitrile, DMSO, propylene glycol, benzyl alcohol, and a combination thereof. 
     
     
         16 . A composition, comprising:
 an adduct of Formula 6 or Formula 7:   
       
         
           
           
               
               
           
         
       
       or a mixture thereof,
 wherein R 1  is a H, OH, 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 or 1; 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; 
 prepared by a process comprising: 
 (a) providing a solution of N-(n-butyl)thiophosphoric triamide (NBPT), the organic solvent, and optionally 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. 
 
     
     
         17 . The composition prepared by the process of  claim 16 , wherein the organic solvent is N-alkyl 2-pyrrolidone, glycerol, isopropylidine glycerol, ethyl acetate, acetonitrile, DMSO, propylene glycol, benzyl alcohol, or a combination thereof. 
     
     
         18 . The composition prepared by the process of  claim 16 , 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. 
     
     
         19 . The composition prepared by the process of  claim 16 , 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. 
     
     
         20 . The composition prepared by the process of  claim 16 , wherein the reaction is carried out at a temperature ranging from about 25° C. to about 40° C. 
     
     
         21 . The composition of  claim 16 , wherein the adducts of Formula 6 are selected from: 
       
         
           
           
               
               
           
         
       
       or a mixture thereof. 
     
     
         22 . The composition of  claim 16 , wherein the adducts of Formula 7 are selected from: 
       
         
           
           
               
               
           
         
       
       or a mixture thereof. 
     
     
         23 . The composition of  claim 16 , wherein the adduct of Formula 7 comprises an adduct of the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         24 . A method for preparing a composition comprising:
 an adduct of Formula 6 or Formula 7:   
       
         
           
           
               
               
           
         
       
       or a mixture thereof,
 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 or 1; 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, 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), the organic solvent, and optionally 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. 
 
     
     
         25 . The method of  claim 24 , wherein the organic solvent is N-alkyl 2-pyrrolidone, glycerol, isopropylidine glycerol, ethyl acetate, acetonitrile, DMSO, propylene glycol, benzyl alcohol, or a combination thereof. 
     
     
         26 . The method of  claim 24 , 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. 
     
     
         27 . The method of  claim 24 , 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. 
     
     
         28 . The method of  claim 24 , wherein the reaction is carried out at a temperature ranging from about 25° C. to about 40° C. 
     
     
         29 . The method of  claim 24 , wherein the adducts of Formula 6 and Formula 7 are selected from: 
       
         
           
           
               
               
           
         
       
       or a mixture thereof.