# US 11,028,024 B2 · Reaction products and methods for making and using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,028,024 B2 - Document ID: US11028024B2 - Status: Granted - Kind: B2 - Application number: 15/929,060 - Filed: 2018-11-12 - Published: 2019-04-18 - Granted: 2021-06-08 - Earliest claimed: 2010-04-30 - Assignees: Koch Agronomic Services, LLC - Applicants: Koch Agronomic Services, LLC - Inventors: Kurt D. Gabrielson; Mary L. Epling - Web page: https://patentgrep.com/patent/US11028024B2 ## CPC - C05G 3/90: for affecting the nitrification of ammonium compounds or urea in the soil - C05C 3/00: Fertilisers containing other salts of ammonia or ammonia itself, e.g. gas liquor - C05C 9/00: Fertilisers containing urea or urea compounds - C05C 9/02: containing urea-formaldehyde condensates - C05G 5/23: Solutions - C09K 15/20: containing nitrogen and oxygen - 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 - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract Reaction products and methods for making and using the same are provided. The reaction products particularly may include adducts of two or more reactants. The adducts particularly can incorporate a nitrification inhibitor, such as DCD. In particular embodiments, reaction products may be formed from the reaction of formaldehyde, DCD, urea, and an ammonia source. The adducts may be included in agricultural products, including fertilizer compositions and nitrification inhibitor systems. Fertilizer compositions including the adducts can be beneficial for reducing leaching of nitrification inhibitors applied to soil. ## Claims ### Claim 1 An agricultural composition comprising: A) a material selected from the group consisting of urea, dicyandiamide (DCD), urea-formaldehyde polymer (UFP), ammonia, and combinations thereof; B) at least one adduct according to the structure of Formula 4 wherein: X is O or R1, R2, R3, and R4 are independently selected from the group consisting of: and wherein, if X=O, at least one of R1, R2, R3, and R4 is and C) a urease inhibitor. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the at least one adduct includes an adduct according to the structure of Formula 5 or Formula 6: ### Claim 3 (depends on 2) The composition according to claim 2, wherein the adduct according to the structure of Formula 5 or Formula 6 is present at a concentration of about 0.1 to about 10 wt. % based on the total weight of the composition. ### Claim 4 (depends on 2) The composition according to claim 2, wherein the adduct according to Formula 5 and the adduct according to Formula 6 are both present in the composition. ### Claim 5 (depends on 1) The composition according to claim 1, wherein the composition is an aqueous mixture. ### Claim 6 (depends on 5) The composition according to claim 5, wherein the aqueous mixture has a pH of 7 or greater. ### Claim 7 (depends on 5) The composition according to claim 5, wherein the aqueous mixture comprises 2-cyano-1-((4-oxo-1,3,5-triazinan-1-yl)methyl)guanidine, 1-((2-cyanoguanidino)methyl)urea, and DCD. ### Claim 8 (depends on 7) The composition according to claim 7, wherein the aqueous mixture further comprises urea or ammonia. ### Claim 9 (depends on 7) The composition according to claim 7, wherein the aqueous mixture further comprises 2-cyano-1-((2-cyanoguanidino)methyl)guanidine. ### Claim 10 (depends on 1) The composition according to claim 1, wherein the urease inhibitor is N-(n-butyl)thiophosphoric triamide (NBPT), N-(n-butyl)phosphoric triamide, thiophosphoryl triamide, phenyl phosphorodiamidate, cyclohexyl phosphoric triamide, cyclohexyl thiophosphoric triamide, phosphoric triamide, hydroquinone, p-benzoquinone, hexamidocyclotriphosphazene, thiopyridines, thiopyrimidines, thiopyridine-N-oxides, N,N-dihalo-2-imidazolidinone, N-halo-2-oxazolidinone, or a combination thereof. ### Claim 11 A nitrification inhibitor system comprising a mixture of: a. a triazonyl-formaldehyde-DCD adduct; b. a urea-formaldehyde-DCD adduct; and c. a urease inhibitor. ### Claim 12 (depends on 11) The nitrification inhibitor system according to claim 11, comprising about 0.1 to 10 wt. % of the triazonyl-formaldehyde-DCD adduct based upon the weight of the nitrification inhibitor system. ### Claim 13 (depends on 11) The nitrification inhibitor system according to claim 11, comprising about 0.1 to 10 wt. % of the urea-formaldehyde-DCD adduct based upon the weight of the nitrification inhibitor system. ### Claim 14 (depends on 11) The nitrification inhibitor system according to claim 11, further comprising about 0.1 to 10 wt. % of a DCD-formaldehyde-oligomer adduct based upon the weight of the nitrification inhibitor system. ### Claim 15 (depends on 11) The nitrification inhibitor system according to claim 11, wherein the mixture further comprises water. ### Claim 16 (depends on 11) The nitrification inhibitor system according to claim 11, wherein the mixture further comprises free DCD. ### Claim 17 (depends on 11) The nitrification inhibitor system according to claim 11, wherein the urease inhibitor is N-(n-butyl)thiophosphoric triamide (NBPT), N-(n-butyl)phosphoric triamide, thiophosphoryl triamide, phenyl phosphorodiamidate, cyclohexyl phosphoric triamide, cyclohexyl thiophosphoric triamide, phosphoric triamide, hydroquinone, p-benzoquinone, hexamidocyclotriphosphazene, thiopyridines, thiopyrimidines, thiopyridine-N-oxides, N,N-dihalo-2-imidazolidinone, N-halo-2-oxazolidinone, or a combination thereof. ### Claim 18 A method for reducing nitrification in soil, the method comprising: applying an agricultural composition to the soil such that nitrification of a nitrogen source in the soil is reduced, wherein the agricultural composition comprises: A) a material selected from the group consisting of urea, dicyandiamide (DCD), urea-formaldehyde polymer (UFP), ammonia, and combinations thereof; B) at least one adduct according to the structure of Formula 4 wherein: X is O or R1, R2, R3, and R4 are independently selected from the group consisting of: and wherein, if X=O, at least one of R1, R2, R3, and R4 is and C) a urease inhibitor. ### Claim 19 (depends on 18) The method according to claim 18, wherein the nitrogen source is combined with the agricultural composition prior to applying the agricultural composition to the soil. ### Claim 20 (depends on 18) The method according to claim 18, wherein any one of the following conditions is met: the amount of the agricultural composition applied to the soil ranges from about 1 kg/ha to about 50 kg/ha; the method comprises applying the nitrogen source to the soil prior to applying the agricultural composition to the soil; and/or the agricultural composition is applied to the soil before a nitrogen source is applied to the soil.