IP Library Granted Patent US 11,981,611
Granted Patent B2
US 11,981,611 · App. 17/892,963 · Granted May 14, 2024

Nitrification inhibitors to improve fertilizer efficiency

Inventors: Gary David McKnight (High Point, NC); Randall Linwood Rayborn (Burlington, NC)
Assignee: SOILGENIC TECHNOLOGIES, LLC
C05F11/08C05C1/00C05C3/00C05C9/00C05C9/02C05C11/00C05F3/00C05F17/00C05G3/90C05G5/23C05G5/27C05G5/30C09D7/20
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Quick Facts
Patent No.
US 11,981,611
App. No.
17/892,963
Granted
May 14, 2024
Kind
B2
Abstract

Disclosed are compositions and methods of making a liquid fertilizer additive of biodegradable polymeric and/or oligomeric nitrification inhibitors comprised of utilizing a non-aqueous polar, aprotic organo liquid (NAPAOL) as the reaction medium for the reaction of aldehyde(s) with cyano-containing nitrification inhibitors that have one or more aldehyde reactive groups selected from the group consisting of a) primary amines, b) secondary amines, c) amides, d) thiols, e) hydroxyls and f) phenols.

Claims (247)

1. A fertilizer composition comprising a) one or more solid nitrogen sources, and b) a liquid fertilizer additive composition, wherein the one or more solid nitrogen sources are nitrogen sources granules, wherein the liquid fertilizer additive composition comprises a liquid reaction composition, wherein the liquid reaction composition comprises i) one or more biodegradable polymers and/or oligomers, and ii) a reaction medium, wherein the one or more biodegradable polymers and/or oligomers comprise one or more dicyandiamide-formaldehyde reaction products, wherein the one or more dicyandiamide-formaldehyde reaction products are formed in the reaction medium, wherein the reaction medium comprises a non-aqueous polar, aprotic solvent (NAPAOL), wherein the NAPAOL comprises one or more polar, aprotic solvents selected from the group consisting of:

(1) dimethyl sulfoxide,

(2) one or more sulfoxides selected from the group consisting of (a) dialkylsulfoxide, (b) diarylsulfoxide, and (c) alkylaryl-sulfoxide having the formula:

R 9 S(O) x R 10 ,

wherein R 9 and R 10 are each independently a C 1-6 alkylene group, an aryl group, or C 1-3 alkylenearyl group or R 9 and R 10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1-6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring and x is 1 or 2,

(3) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate,

(4) 1-Methyl-2-pyrrolidone,

(5) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the group represented by the formula:

wherein:

R 22 is alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is alkyl radical —C 1 H 3 to —C 6 H 13

(6) 1,2-dimethyloxyethane,

(7) 2-methoxyethyl ether, and

(8) cyclohexylpyrrolidone,

wherein the reaction medium's properties are:

a) environmentally safe,

b) flashpoint above 145° F.,

c) safe for contact with humans and animals,

d) able to maintain the one or more dicyandiamide-formaldehyde reaction products at levels of 1-50% in down to at least 10° C., and

e) provide even delivery of the one or more dicyandiamide-formaldehyde reaction products to the surface of a fertilizer granules and to the surface of the nitrogen sources granules while not causing clumping of the granules, and

wherein said liquid fertilizer additive composition comprises 0.05-10% of the fertilizer composition.

2. The fertilizer composition of claim 1 , wherein the liquid reaction composition comprises the one or more dicyandiamide-formaldehyde reaction products comprising the following one or more structures:

wherein R 43 , R 44 , R 45 and R 46 are one or more members independently selected from the group consisting of: H and —CH 2 OH wherein at least one of R 43 , R 44 , R 45 and R 46 is —CH 2 OH,

wherein R 47 , R 48 , R 49 R 50 , R 51 and R 52 are one or more members independently selected from the group consisting of: H, and —CH 2 OH,

wherein R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 are one or more members independently selected from the group consisting of: H and —CH 2 OH, and

wherein R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , R 67 and R 68 are one or more members independently selected from the group consisting of: H and —CH 2 OH, wherein x is 2-20, and

wherein said one or more dicyandiamide-formaldehyde reaction products are made by using non-aqueous reaction conditions, and wherein said liquid reaction composition comprises more than 10% by weight of said one or more structures.

3. The fertilizer composition of claim 1 , wherein the liquid fertilizer additive composition further comprises one or more members selected from the group consisting of: a) paraformaldehyde, b) dicyandiamide (DCD) and c) formaldehyde.

4. The fertilizer composition of claim 1 , wherein the liquid fertilizer additive composition imparts one or more properties to the fertilizer composition selected from the group consisting of:

e) increase crush resistance of the one or more nitrogen sources granules

f) impart lower water solubility of fertilizer composition

g) provide nitrification inhibition to the one or more nitrogen sources granules

h) provide extended available of nitrogen in a plant available form

i) reduce migration of nitrification inhibitors through the soil.

5. The fertilizer composition of claim 1 , wherein the liquid fertilizer additive composition further comprises one or more members selected from the group consisting of:

j) surfactants, buffers, fragrance/odor masking agents, colorants, flow modifiers, silicas, and hydrophobized silicas, and

k) one or more non-aqueous organo liquids selected from the group consisting of one or more additional polar aprotic solvents, one or more aprotic solvents, and one or more protic solvents wherein:

the one or more aprotic solvents are selected from the group consisting of:

i) one or more polyols capped with acetate or formate wherein a polyol portion is selected from the group consisting of ethylene glycol, 1,3 propylene glycol, 1,2 propylene glycol, butylene glycol, trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose and glycerin,

ii) one or more alkylene glycol alkyl ether acetates selected from the group consisting of dipropylene glycol methyl ether acetate, tripropylene glycol methyl ether acetate, and tripropylene glycol butyl ether acetate,

iii) isophorone,

iv) one or more diesters selected from the group consisting of dimethylsuccinate, dimethyl adipate, diethyl glutarate, and dimethyl glutarate,

v) dimethylacetamide,

vi) dimethylformamide,

vii) dimethyl-2-imidazolidinone,

viii) 1-Methyl-2-pyrrolidone, and

ix) limonene,

wherein the one or more protic solvents are selected from the group consisting of:

i) an alcohol from the family of C 1-10 alkanols,

ii) one or more polyols selected from the group consisting of trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose, and glycerin,

iii) one or more poly(C 1-10 alkylene) glycols represented by the structure:

H(C t H u ) v OH,

wherein

t is an integer: 1-10

u is an integer: 2-20

and v is an integer: 1-20,

iv) one or more alkylene glycols selected from the group consisting of ethylene glycol, 1,3 propylene glycol, 1,2 propylene glycol, and butylene glycol,

v) isopropylidene glycerol,

vi) one or more alkylene glycol alkyl ethers selected from the group represented by the structure:

wherein R 1 is: CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9

wherein R 2 is: H or the structure

wherein R 3 is: H or CH 3

wherein R 4 is H or CH 3

and f is an integer between 1 and 15,

vii) one or more alkyl lactates selected from the group consisting of ethyl lactate, propyl lactate and butyl lactate,

viii) one or more alkanolamines selected from the group represented by the structure:

wherein R 5 is: C 2 H 4 OR 8 or C 3 H 6 OH

wherein R6 is: H, C2H4OR8 or C3H6OH

wherein R 7 is: H, C 2 H 4 OR 8 or C 3 H 6 OH

wherein R 8 is: (C 2 H 4 O) g H

and g is an integer between 1-10, and

ix) i glycerol carbonate, and

wherein one or more additional polar aprotic solvents are selected from the group consisting of:

i) dimethyl sulfoxide,

ii) one or more sulfoxides selected from the group consisting of (1) dialkylsulfoxide, (2) diarylsulfoxide, and (3) alkylaryl-sulfoxide having the formula:

R 9 S(O) x R 10 ,

wherein R 9 and R 10 are each independently a C 1-6 alkylene group, an aryl group, or C 1-3 alkylenearyl group or R 9 and R 10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1-6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring and x is 1 or 2,

iii) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate,

iv) 1-Methyl-2-pyrrolidone,

v) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the group represented by the formula:

wherein:

R 22 is alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is alkyl radical —C 1 H 3 to —C 6 H 13 ,

vi) 2-dimethyloxyethane,

vii) 2-methoxyethyl ether, and

viii) cyclohexylpyrrolidone.

6. The fertilizer composition of claim 1 , wherein the fertilizer composition further comprises one or more members selected from the group consisting of:

l) surfactants, buffers, fragrance/odor masking agents, colorants, flow modifiers, silicas, and hydrophobized silicas, and

m) one or more non-aqueous organo liquids selected from the group consisting of one or more additional polar aprotic solvents, one or more aprotic solvents, and one or more protic organo solvents wherein:

the one or more aprotic solvents are selected from the group consisting of:

i) one or more polyols capped with acetate or formate wherein a polyol portion is selected from the group consisting of ethylene glycol, 1,3 propylene glycol, 1,2 propylene glycol, butylene glycol, trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose and glycerin,

ii) one or more alkylene glycol alkyl ether acetates selected from the group consisting of dipropylene glycol methyl ether acetate, tripropylene glycol methyl ether acetate, and tripropylene glycol butyl ether acetate,

iii) isophorone,

iv) one or more diesters selected from the group consisting of dimethylsuccinate, dimethyl adipate, diethyl glutarate, and dimethyl glutarate,

v) dimethylacetamide,

vi) dimethylformamide,

vii) dimethyl-2-imidazolidinone,

viii) 1-Methyl-2-pyrrolidone, and

ix) limonene,

wherein the one or more protic solvents are selected from the group consisting of:

i) an alcohol from the family of C 1-10 alkanols,

ii) one or more polyols selected from the group consisting of trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose, and glycerin,

iii) one or more poly(C 1-10 alkylene) glycols represented by the structure:

H(C t H u ) v OH, wherein

t is an integer: 1-10

u is an integer: 2-20

and v is an integer: 1-20,

iv) one or more alkylene glycols selected from the group consisting of ethylene glycol, 1,3 propylene glycol, 1,2 propylene glycol, and butylene glycol,

v) isopropylidene glycerol,

vi) one or more alkylene glycol alkyl ethers selected from the group represented by the structure:

wherein R 1 is: CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9

wherein R 2 is: H or the structure

wherein R 3 is: H or CH 3

wherein R 4 is H or CH 3

and f is an integer between 1 and 15,

vii) one or more alkyl lactates selected from the group consisting of ethyl lactate, propyl lactate and butyl lactate,

viii) one or more alkanolamines selected from the group represented by the structure:

wherein R 5 is: C 2 H 40 R 8 or C 3 H 6 OH

wherein R 6 is: H, C 2 H 4 OR 8 or C 3 H 6 OH

wherein R 7 is: H, C 2 H 40 R 8 or C 3 H 6 OH

wherein R 8 is: (C 2 H 40 ) g H

and g is an integer between 1-10, and

ix) iglycerol carbonate, and

wherein one or more additional polar aprotic solvents are selected from the group consisting of:

a dimethyl sulfoxide,

b) one or more sulfoxides selected from the group consisting of (1) dialkylsulfoxide, (2) diarylsulfoxide, and (3) alkylaryl-sulfoxide(s) having the formula:

R 9 S(O) x R 10 ,

wherein R 9 and R 10 are each independently a C 1-6 alkylene group, an aryl group, or C 1-3 alkylenearyl group or R 9 and R 10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1 6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring and x is 1 or 2,c) one or more alkylene carbonates selected from the group consisting of ethylene

carbonate, propylene carbonate and butylene carbonate,

d) 1-Methyl-2-pyrrolidone,

e) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the group represented by the formula:

wherein:

R 22 is alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is alkyl radical —C 1 H 3 to —C 6 H 13 ,

f) 2-dimethyloxyethane,

g) 2-methoxyethyl ether, and

h) cyclohexylpyrrolidone.

7. The fertilizer composition of claim 1 , wherein the fertilizer composition further comprises one or more members selected from the group consisting of:

n) one or more biologics selected from the group consisting of:

i) Bacillus biologics, ii) Azospirillum biologics, iii) Azobacter biologics iv) Gluconacetobacter biologics, v) Phosphobacteria , vi) Cyanobacteria , vii) Herbaspirillum , viii) Burkholderia , ix) Pseudomonas , x) Gluconacetobacter , xi) Enterobacter , xii) Klebsiella , xiii) Burkholderia , xiv) Bradyrhiwbium species, xv) Bradyrhiwbium japonicum , xvi) Rhizobium meliloti , xvii) Laccaria bicolor , xviii) Glomus imraradices timanita , xix) Actinomyces , xx) Penicillium , xxi) Mesorhizobiwn cicero, xxii) one or more insecticidal or insect repellent microbial species and strains are selected from the group consisting of:

Telenomus podisi, Baculovirus anticarsia; Trichogramma pretiosum, Trichogramma gallai, Chromobacterium subtsugae, Trichoderma fertile, Beauveria bassiana, Beauveria bassiana, Beauveria bassiana, Paecilomyces jknwsoroseu, Trichoderma harzianum, Verticillium lecanii, lsarfofumosarosea Lecanicillium muscarium, Streptomyces microflavus , and Muscodor albus,

xxiii) one or more nematodal microbial species and strains are selected from the group consisting of:

Myrothecium verrucaria, Pasteuria species, Pasteuria Metarhizium species, and Flavobacteriwn species

xxiv) Reynoutria sachalinensis and

xxv) one or more antifungal, antimicrobial and/or plant growth promoting microbial species and strains are selected from the group consisting of: Gliocladium species, and one or more Pseudomonas species selected from the group consisting of:

Pseudomonas fluorescens, Pseudomonas fluorescens, Putida and P. chlororaphis, Pseudomonas fluorescens VP5, Pseudomonas diazotrophicus, Enterobacter cloacae, Trichodema species, Trichoderma virens, Trichoderma atroviride strains, Coniothyrium minitans, Gliocladium species, Gliacladium virens, Gliacladium roseum , and Trichodemw harzianum species,

b) and one or more biologically active agents selected from the group consisting of:

i) one or more nitrification inhibitors are selected from the group consisting of 2-chloro-6-(trichloromethyl)pyridine, 4-amino-1,2,4,6-triazole-HCl, 2,4-diamino-6-trichloromethyltriazine CL-1580, dicyandiamide (DCD), thiourea, 1-mercapto-1,2,4-triazole, ammonium thiosulfate, dimethylpyrazole organic and inorganic salts, and 2-amino-4-chloro-6-methylpyrimidine, and

ii) one or more members selected from the group consisting of (1) one or more pesticides, (2) one or more herbicides, (3) one or more fungicides, (4) one or more insecticides and (5) combinations thereof.

8. The fertilizer composition of claim 1 , wherein the liquid fertilizer additive composition further comprises one or more members selected from the group consisting of:

a) one or more biologics selected from the group consisting of:

i) Bacillus biologics, ii) Azospirillum biologics, iii) Azobacter biologics iv) Gluconacetobacter biologics, v) Phosphobacteria , vi) Cyanobacteria , vii) Herbaspirillum , viii) Burkholderia , ix) Pseudomonas , x) Gluconacetobacter , xi) Enterobacter , xii) Klebsiella , xiii) Burkholderia , xiv) Bradyrhiwbium species, xv) Bradyrhiwbium japonicum , xvi) Rhizobium meliloti , xvii) Laccaria bicolor , xviii) Glomus imraradices timanita, xix) Actinomyces , xx) Penicillium , xxi) Mesorhizobiwn cicero, xxii) one or more insecticidal or insect repellent microbial species and strains are selected from the group consisting of:

Telenomus podisi, Baculovirus anticarsia; Trichogramma pretiosum, Trichogramma gallai, Chromobacterium subtsugae, Trichoderma fertile, Beauveria bassiana, Beauveria bassiana, Beauveria bassiana, Paecilomyces jknwsoroseu, Trichoderma harzianum, Verticillium lecanii, lsarfofumosarosea Lecanicillium muscarium, Streptomyces microflavus , and Muscodor albus,

xxiii) one or more nematodal microbial species and strains are selected from the group consisting of:

Myrothecium verrucaria, Pasteuria species, Pasteuria Metarhizium species, and Flavobacteriwn species

xxiv) Reynoutria sachalinensis and

xxv) one or more antifungal, antimicrobial and/or plant growth promoting microbial species and strains are selected from the group consisting of: Gliocladium species, and one or more Pseudomonas species selected from the group consisting of:

Pseudomonas fluorescens, Pseudomonas fluorescens, Putida and P. chlororaphis, Pseudomonas fluorescens VP5, Pseudomonas diazotrophicus, Enterobacter cloacae, Trichodema species, Trichoderma virens, Trichoderma atroviride strains, Coniothyrium minitans, Gliocladium species, Gliacladium virens, Gliacladium roseum , and Trichodemw harzianum species,

and one or more biologically active agents selected from the group consisting of:

i) one or more nitrification inhibitors are selected from the group consisting of 2-chloro-6-(trichloromethyl)pyridine, 4-amino-1,2,4,6-triazole-HCl, 2,4-diamino-6-trichloromethyltriazine CL-1580, dicyandiamide (DCD), thiourea, 1-mercapto-1,2,4-triazole, ammonium thiosulfate, dimethylpyrazole organic and inorganic salts, and 2-amino-4-chloro-6-methylpyrimidine, and

ii) one or more members selected from the group consisting of (1) one or more pesticides, (2) one or more herbicides, (3) one or more fungicides, (4) one or more insecticides and (5) combinations thereof.

9. The fertilizer composition of claim 1 , wherein the one or more nitrogen sources comprise ammonium sulfate.

10. The fertilizer composition of claim 1 , wherein the one or more nitrogen sources comprise ammonium nitrate.

11. The fertilizer composition of claim 1 , wherein the one or more nitrogen sources comprise one or more ammonium phosphates selected from the group consisting of a) diammonium phosphate, and b) monoammonium phosphate.

12. The fertilizer composition of claim 1 , wherein the fertilizer composition further comprises one or more biologically active agents, wherein the one or more biologically active agents comprise dicyandiamide.

13. The fertilizer composition of claim 1 , wherein the liquid fertilizer additive composition further comprises one or more biologically active agents, wherein the one or more biologically active agents comprise dicyandiamide.

14. The fertilizer composition of claim 1 , wherein the NAPAOL comprises dimethyl sulfoxide.

15. The fertilizer composition of claim 1 wherein the composition is made by evenly coating the nitrogen sources granules with said liquid fertilizer additive composition using spraying, metering or slowly pouring the liquid fertilizer additive onto the surface of the nitrogen sources granules, using: a) a mixing tank, b) a blender, or c) a tumbler.

16. A fertilizer composition comprising a) one or more solid nitrogen sources, and b) a liquid fertilizer additive composition, wherein the one or more solid nitrogen sources are nitrogen sources granules, wherein the liquid fertilizer additive composition comprises i) a liquid reaction composition and ii) one or more nitrification inhibitors, wherein the liquid reaction composition comprises i) one or more biodegradable polymers and/or oligomers, and ii) a reaction medium, wherein the one or more biodegradable polymers and/or oligomers comprise one or more dicyandiamide-formaldehyde reaction products, wherein the one or more dicyandiamide-formaldehyde reaction products are formed in the reaction medium, wherein the reaction medium comprises a non-aqueous polar, aprotic solvent (NAPAOL), wherein the NAPAOL comprises one or more polar, aprotic solvents selected from the group consisting of:

(1) dimethyl sulfoxide,

(2) one or more sulfoxide selected from the group consisting of (a) dialkylsulfoxide, (b) diarylsulfoxide, and (c) alkylaryl-sulfoxide having the formula:

R 9 S(O) x R 10

wherein R 9 and R 10 are each independently a C 1-6 alkylene group, an aryl group, or C 1-3 alkylenearyl group or R 9 and R 10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1-6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring and x is 1 or 2,

(3) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate

(4) 1-Methyl-2-pyrrolidone,

(5) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the structure:

wherein:

R 22 is an alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is an alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is an alkyl radical —C 1 H 3 to —C 6 H 13

(6) 1,2-dimethyloxyethane,

(7) 2-methoxyethyl ether, and

(8) cyclohexylpyrrolidone,

and wherein the one or more dicyandiamide-formaldehyde reaction products comprise one or more structures:

wherein R 43 , R 44 , R 45 and R 46 are one or more members independently selected from the group consisting of: H and —CH 2 OH wherein at least one of R 43 , R 44 , R 45 and R 46 is —CH 2 OH,

wherein R 47 , R 48 , R 49 R 50 , R 51 and R 52 are one or more members independently selected from the group consisting of: H, and —CH 2 OH,

wherein R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 are one or more members independently selected from the group consisting of: H and —CH 2 OH, wherein said liquid fertilizer additive composition is generated under non-aqueous conditions,

wherein R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , R 67 and R 68 are one or more members

independently selected from the group consisting of: H and —CH 2 OH, wherein said one or more dicyandiamide-formaldehyde reaction products are made by using non-aqueous reaction conditions, and wherein said liquid reaction composition comprises more than 10% by weight of said one or more structures.

17. The fertilizer composition of claim 16 , wherein the composition further comprises one or more members selected from the group consisting of:

a) surfactants, buffers, fragrance/odor masking agents, colorants, flow modifiers, silicas, and hydrophobized silicas, dimethyl sulfoxide,

b) a one or more non-aqueous organo liquids selected from the group consisting of one or more additional polar aprotic solvents, one or more aprotic solvents, and one or more protic solvents wherein:

the one or more aprotic solvents are selected from the group consisting of:

i) one or more polyols capped with acetate or formate wherein a polyol portion is selected from the group consisting of ethylene glycol, 1,3 propylene glycol, 1,2 propylene glycol, butylene glycol, trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose and glycerin,

ii) one or more alkylene glycol alkyl ether acetates selected from the group consisting of dipropylene glycol methyl ether acetate, tripropylene glycol methyl ether acetate, and tripropylene glycol butyl ether acetate,

iii) isophorone,

iv) one or more diesters selected from the group consisting of dimethylsuccinate, dimethyl adipate, diethyl glutarate, and dimethyl glutarate,

v) dimethylacetamide,

vi) dimethylformamide,

vii) dimethyl-2-imidazolidinone,

viii) 1-Methyl-2-pyrrolidone, and

ix) limonene,

wherein the one or more protic solvents are selected from the group consisting of:

i) an alcohol from the family of C 1-10 alkanols,

ii) one or more polyols selected from the group consisting of trimethylol propane, trimethylol ethane, pentaerythritol, sorbitol, sorbitan, glucose, fructose, galactose, and glycerin,

iii) one or more poly(C 1-10 alkylene) glycols represented by the structure:

H(CtH u ) v OH, wherein

t is an integer: 1-10,

u is an integer: 2-20,

and v is an integer: 1-20,

iv) one or more alkylene glycols selected from the group consisting of ethylene glycol, 1,3-propylene glycol, 1,2-propylene glycol, and butylene glycol,

v) isopropylidene glycerol,

vi) one or more alkylene glycol alkyl ethers selected from the group represented by the structure: vi) one or more alkylene glycol alkyl ethers selected from the group represented by the structure:

wherein R 1 is: CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9 ,

wherein R 2 is: H or the structure

wherein R 3 is: H or CH 3

wherein R 4 is H or CH 3

and f is an integer between 1 and 15,

vii) one or more alkyl lactates selected from the group consisting of ethyl lactate, propyl lactate and butyl lactate,

viii) one or more alkanolamines selected from the group represented by the structure:

wherein R 5 is: C 2 H 4 OR 8 or C 3 H 6 OH,

wherein R 6 is: H, C 2 H 4 OR 8 or C 3 H 6 OH,

wherein R 7 is: H, C 2 H 4 OR 8 or C 3 H 6 OH,

wherein R 8 is: (C 2 H 40 ) g H, and

g is an integer between 1-10, and

ix) glycerol carbonate, and

wherein one or more additional polar aprotic solvents are selected from the group consisting of:

i) dimethyl sulfoxide,

ii) one or more sulfoxide selected from the group consisting of (1) dialkylsulfoxide, (2) diarylsulfoxide, and (3) alkylaryl-sulfoxide having the formula:

R 9 S(O) x R 10 ,

wherein R 9 and R 10 are each independently a C 1-6 alkylene group, an aryl group, or C 1-3 alkylenearyl group or R 9 and R 10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1-6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring and x is 1 or 2,

iii) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate,

iv) 1-Methyl-2-pyrrolidone,

v) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the group represented by the formula:

wherein:

R 22 is alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is alkyl radical —C 1 H 3 to —C 6 H 13 ,

vi) 2-dimethyloxyethane,

vii) 2-methoxyethyl ether, and

viii) cyclohexylpyrrolidone.

18. The fertilizer composition of claim 16 , wherein the fertilizer composition comprises the one or more nitrification inhibitors selected from the group consisting of: 2-chloro-6-trichloromethyl)pyridine, 4-amino-1,2,4,6-triazole-HCl, 2,4-diamino-6-trichloromethyltriazine CL-1580, dicyandiamide (DCD), thiourea, 1-mercapto-1,2,4-triazole, ammonium thiosulfate, dimethylpyrazole organic and inorganic salts, and 2-amino-4-chloro-6-methylpyrimidine.

19. The fertilizer composition of claim 16 , wherein the liquid fertilizer additive composition comprises the one or more nitrification inhibitors selected from the group consisting of: 2-chloro-6-trichloromethyl)pyridine, 4-amino-1,2,4,6-triazole-HCl, 2,4-diamino-6-trichloromethyltriazine CL-1580, dicyandiamide (DCD), thiourea, 1-mercapto-1,2,4-triazole, ammonium thiosulfate, dimethylpyrazole organic and inorganic salts, and 2-amino-4-chloro-6-methylpyrimidine.

20. The fertilizer composition of claim 16 , wherein the NAPAOL comprises dimethyl sulfoxide.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2023
From: MCKNIGHT, GARY DAVID, MR.; RAYBORN, RANDALL LINWOOD, MR.
To: WORLD SOURCE ENTERPRISES, LLC
Reel/Frame 064408/0851 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2023
From: WORLD SOURCE ENTERPRISES, LLC
To: SOILGENIC TECHNOLOGIES, LLC
Reel/Frame 064409/0077 →
Continuity (7)
Continuation 16154640 · Oct 8, 2018
Continuation In Part 15985656 · May 21, 2018
Continuation In Part 15957575 · Apr 19, 2018
Continuation In Part 15854319 · Dec 26, 2017
Continuation In Part 15641264 · Jul 4, 2017
Provisional Application 62358116 · Jul 4, 2016
Related Publication 20230013743A1 · Jan 19, 2023
Cited By (2)
US 12,365,639 US 12,623,979