WO2020100032A1

WO2020100032A1 - Composition comprising an adduct of urea, formaldehyde, and n-(n-butyl)thiophosphoric triamide and a surfactant

Info

Publication number: WO2020100032A1
Application number: PCT/IB2019/059708
Authority: WO
Inventors: Ethel Garnier-Amblard; Stanley Freeman; Douglas Barr; Kurt D. Gabrielson
Original assignee: Koch Agronomic Services, Llc
Priority date: 2018-11-13
Filing date: 2019-11-12
Publication date: 2020-05-22
Also published as: AR117065A1

Abstract

The present disclosure relates to a stable liquid formulation comprising one or more adducts formed from a reaction of urea, formaldehyde, and a urease inhibitor, and a surfactant, and optionally a urease inhibitor, such as N-(n-butyl) thiophosphoric triamide (NBPT). Methods to make and use such a formulation are also described.

Description

COMPOSITION COMPRISING AN ADDUCT OF UREA, FORMALDEHYDE, AND

N-(N-BUTYL)THIOPHOSPHORIC TRIAMIDE AND A SURFACTANT

[0001] The present disclosure relates to a stable liquid formulation comprising one or more adducts formed from a reaction of urea, formaldehyde, and a urease inhibitor, and a surfactant, and optionally a urease inhibitor, such as /V-(n-butyl) thiophosphoric triamide (NBPT). Despite using water soluble components, adducts prepared from a reaction of a urease inhibitor, formaldehyde, and urea tend to form a viscous sticky gel when contacted with water or urea ammonium nitrate (UAN) solutions. This unanticipated behavior can be alleviated by the addition of certain surfactants. A surfactant reduces milking or flocculation and prevents gel formation.

[0002] Fertilizers have been used for some time to provide nitrogen to the soil. The most widely used and agriculturally important nitrogen fertilizer is urea, CO(NH2)2. Most of the urea currently produced is used as a fertilizer in its granular (or prilled) form. After application of urea to soil, it is readily hydrolyzed to yield ammonia and carbon dioxide. This process is catalyzed by the enzyme urease, which is produced by some bacteria and fungi that may be present in the soil. The gaseous products formed by the hydrolysis reaction (i.e., ammonia and carbon dioxide) can volatilize to the atmosphere and thus, substantial losses from the total amount of the nitrogen applied to the soil can occur.

[0003] Attempts to reduce losses of applied nitrogen have utilized urease inhibitors and/or nitrification inhibitors as additives to the fertilizer. Urease inhibitors are compounds capable of inhibiting the catalytic activity of the urease enzyme on urea in the soil. Nitrification inhibitors are compounds capable of inhibiting the bacterial oxidation of ammonium to nitrate in the soil. Urease inhibitors and nitrification inhibitors can be associated with fertilizers in various ways. For example, they can be coated onto fertilizer granules or mixed into fertilizer matrices. A number of granulation methods are known, including falling curtain, spherudization-agglomeration drum granulation, prilling and fluid bed granulation technologies.

[0004] When incorporated into a urea-containing fertilizer, /V-(n-butyl) thiophosphoric triamide (NBPT) reduces the rate at which urea is hydrolyzed in the soil to ammonia. The benefits realized as a result of the delayed urea hydrolysis include the following: (1) nutrient nitrogen is available to the plant over a longer period of time; (2) excessive build-up of ammonia in the soil following the application of the urea-containing fertilizer is avoided; (3) the potential for nitrogen loss through ammonia volatilization is reduced; (4) the potential for damage by high levels of ammonia to seedlings and young plants is reduced; (5) plant uptake of nitrogen is increased; and (6) an increase in crop yields is attained.

[0005] Industrial grade NBPT is a solid, waxy compound, and decomposes by the action of water, acid and/or elevated temperature. In particular, NBPT is believed to degrade at elevated temperatures into compounds that may not provide the desired inhibitory effects on the urease enzyme. The urease inhibiting potential of NBPT can be increased by mixing it with one or more adducts prepared from a urease inhibitor such as NBPT, formaldehyde, and urea.

[0006] Such compositions generally comprise a reaction product between a urease inhibitor (e.g., /V-(n-butyl) thiophosphoric triamide, NBPT), urea, and formaldehyde. Such reaction products can be characterized as adducts, as the products arising from the reaction retain at least portions of two or more of the reactants (i.e., urease inhibitor, urea, and/or formaldehyde). The reaction products or adducts are represented by the following structures:

Adduct III Adduct IV

[0007] Such adducts have previously been described in U.S. Publication No. US 2017/0022120 Al, now U.S. Patent No. US 9,725,372 B2, which are incorporated by reference herein.

[0008] As mentioned, in contrast to the individual molecules NBPT, urea, and formaldehyde, the adducts of NBPT, urea, and formaldehyde display a different solubility profile in aqueous media and are poorly soluble in water and aqueous solutions. Formulations containing these adducts without surfactant tend to form viscous, sticky gels on contact with aqueous solutions, such as urea ammonium nitrate (UAN) solutions. This behavior makes handling and mixing of final formulations of NBPT and adducts in an aqueous media difficult. It was surprisingly found that in formulations containing the adducts, one or more surfactants help to stabilize and homogenize the formulations and prevent milking, flocculation, and gel formation in contact with UAN or water. The addition of a surfactant may also prevent milking and flocculation when the treated UAN solution is stored at ambient temperature or lower temperatures, such as 0 °C or lower, for an extended period of time.

[0009] The present disclosure provides a formulation comprising one or more adducts of NBPT, urea, and formaldehyde and a surfactant. The present disclosure also includes a formulation comprising one more adducts of NBPT, urea, and formaldehyde, a surfactant, and NBPT. The present formulations may include a solvent, such as an organic solvent, that solubilizes NBPT and the adduct. The present formulations may also include one or more additives. The formulations of the present disclosure may also be added to water-based media (such as a UAN solution) to form a fertilizer. The fertilizers of the present disclosure are resistant to milking, flocculation, and gel formation upon extended exposure to ambient and lower temperatures at 0 °C or below.

[0010] For example, the present disclosure provides a formulation comprising NBPT and an adduct of NBPT, urea, and formaldehyde in an amount ranging from about 15% to about 70% by weight; and a surfactant in an amount ranging from about 0.1% to about 15% by weight, and methods to make and use such a formulation.

[0011] In one embodiment, the present disclosure provides a formulation comprising:

i) an adduct of NBPT, urea, and formaldehyde; and ii) NBPT in a combined amount

ranging from about 15% to about 70% by weight of the total formulation;

iii) a surfactant in an amount ranging from about 0.1 % to about 15% by weight;

iv) a glycol and/or a glycol derivative in an amount ranging from about 20% to about 90% by weight;

v) optionally /V-methyl-2-pyrrolidinone (NMP) in an amount ranging from about 1% to about 30% by weight; and

vi) optionally one or more additives.

Formulations of the present disclosure may further comprise a co-solvent, second surfactant, a viscosity reducer, water, a dye, and a defoamer.

[0012] The adducts of NBPT, urea, and formaldehyde of the present disclosure include any of the following structures:

Adduct III Adduct IV

[0013] The formulations of the present disclosure comprise an adduct of NBPT, urea, and formaldehyde in an amount ranging from about 15% to about 70% by weight based on the total weight of the formulation. For example, an adduct of NBPT, urea, and formaldehyde is present in an amount ranging from about 15% to about 20%, from about 20% to about 25%, from about 25% to about 30%, from about 30% to about 35%, from about 35% to about 40%, from about 40% to about 45%, from about 45% to about 50%, from about 50% to about 55%, from about 55% to about 60%, from about 60% to about 65%, from about 65% to about 70%, by weight based on the total formulation.

[0014] In at least one embodiment, the adduct of NBPT, urea, and formaldehyde ranges from about 15.0% to about 16.0% by weight, such as from about 16.0% to about 17.0%, such as from about 17.0% to about 18.0%, such as from about 18.0% to about 19.0%, such as from about 19.0% to about 20.0%, such as from about 20.0% to about 21.0%, such as from about 21.0% to about 22.0%, such as from about 22.0% to about 23.0%, such as from about 23.0% to about 24.0%, such as from about 24.0% to about 25.0%, such as from about 25.0% to about 26.0%, such as from about 26.0% to about 27.0%, such as from about 27.0% to about 28.0%, such as from about 28.0% to about 29.0%, such as from about 29.0% to about 30.0%, such as from about 30.0% to about 31.0%, such as from about 31.0% to about 32.0%, such as from about 32.0% to about 33.0%, such as from about 33.0% to about 34.0%, such as from about 34.0% to about 35.0%, such as from about 35.0% to about 36.0%, such as from about 36.0% to about 37.0%, such as from about 37.0% to about 38.0%, such as from about 38.0% to about 39.0%, such as from about 39.0% to about 40.0%, such as from about 40.0% to about 41.0%, such as from about 41.0% to about 42.0%, such as from about 42.0% to about 43.0%, such as from about 43.0% to about 44.0%, such as from about 44.0% to about 45.0%, such as from about 45.0% to about 46.0%, such as from about 46.0% to about 47.0%, such as from about 47.0% to about 48.0%, such as from about 48.0% to about 49.0%, such as from about 49.0% to about 50.0%, such as from about 50.0% to about 51.0%, such as from about 51.0% to about 52.0%, such as from about 52.0% to about 53.0%, such as from about 53.0% to about 54.0%, such as from about 54.0% to about 55.0%, such as from about 55.0% to about 56.0%, such as from about 56.0% to about 57.0%, such as from about 57.0% to about 58.0%, such as from about 58.0% to about 59.0%, such as from about 59.0% to about 60.0%, such as from about 60.0% to about 61.0%, such as from about 61.0% to about 62.0%, such as from about 62.0% to about 63.0%, such as from about 63.0% to about 64.0%, such as from about 64.0% to about 65.0%, such as from about 65.0% to about 66.0%, such as from about 66.0% to about 67.0%, such as from about 67.0% to about 68.0%, such as from about 68.0% to about 69.0%, such as from about 69.0% to about 70.0%.

[0015] The formulations of the present disclosure comprise NBPT and an adduct of NBPT, urea, and formaldehyde in a combined amount ranging from about 15% to about 70% by weight based on the total weight of the formulation. For example, NBPT and an adduct of NBPT, urea, and formaldehyde are present in a combined amount ranging from about 15% to about 20%, from about 20% to about 25%, from about 25% to about 30%, from about 30% to about 35%, from about 35% to about 40%, from about 40% to about 45%, from about 45% to about 50%, from about 50% to about 55%, from about 55% to about 60%, from about 60% to about 65%, from about 65% to about 70%, by weight based on the total formulation.

[0016] In at least one embodiment, the combined amount of NBPT and an adduct of NBPT, urea, and formaldehyde ranges from about 15.0% to about 16.0% by weight, such as from about 16.0% to about 17.0%, such as from about 17.0% to about 18.0%, such as from about 18.0% to about 19.0%, such as from about 19.0% to about 20.0%, such as from about 20.0% to about 21.0%, such as from about 21.0% to about 22.0%, such as from about 22.0% to about 23.0%, such as from about 23.0% to about 24.0%, such as from about 24.0% to about 25.0%, such as from about 25.0% to about 26.0%, such as from about 26.0% to about 27.0%, such as from about 27.0% to about 28.0%, such as from about 28.0% to about 29.0%, such as from about 29.0% to about 30.0%, such as from about 30.0% to about 31.0%, such as from about 31.0% to about 32.0%, such as from about 32.0% to about 33.0%, such as from about 33.0% to about 34.0%, such as from about 34.0% to about 35.0%, such as from about 35.0% to about 36.0%, such as from about 36.0% to about 37.0%, such as from about 37.0% to about 38.0%, such as from about 38.0% to about 39.0%, such as from about 39.0% to about 40.0%, such as from about 40.0% to about 41.0%, such as from about 41.0% to about 42.0%, such as from about 42.0% to about 43.0%, such as from about 43.0% to about 44.0%, such as from about 44.0% to about 45.0%, such as from about 45.0% to about 46.0%, such as from about 46.0% to about 47.0%, such as from about 47.0% to about 48.0%, such as from about 48.0% to about 49.0%, such as from about 49.0% to about 50.0%, such as from about 50.0% to about 51.0%, such as from about 51.0% to about 52.0%, such as from about 52.0% to about 53.0%, such as from about 53.0% to about 54.0%, such as from about 54.0% to about

55.0%, such as from about 55.0% to about 56.0%, such as from about 56.0% to about 57.0%, such as from about 57.0% to about 58.0%, such as from about 58.0% to about 59.0%, such as from about 59.0% to about 60.0%, such as from about 60.0% to about 61.0%, such as from about 61.0% to about 62.0%, such as from about 62.0% to about 63.0%, such as from about 63.0% to about 64.0%, such as from about 64.0% to about 65.0%, such as from about 65.0% to about 66.0%, such as from about 66.0% to about 67.0%, such as from about 67.0% to about 68.0%, such as from about 68.0% to about 69.0%, such as from about 69.0% to about 70.0%.

[0017] The formulations of the present disclosure also include one or more surfactants. Examples of surfactants include, but are not limited to, an alkylene glycol alkyl ether, a nonionic surfactant, a sorbitan surfactant, a phosphate ester or a mixture of phosphate esters, and an anionic surfactant.

[0018] Examples of an alkylene glycol alkyl ether include but are not limited to diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monopentyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, tri ethylene glycol monopropyl ether, tri ethylene glycol monobutyl ether, tri ethylene glycol monopentyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monoisobutyl ether, triethylene glycol monohexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monopentyl ether, tetraethylene glycol monoisopropyl ether, tetraethylene glycol monoisobutyl ether, tetraethylene glycol monohexyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopentyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol monohexyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monopentyl ether, tripropylene glycol monoisopropyl ether, tripropylene glycol monoisobutyl ether, and tripropylene glycol monohexyl ether.

[0019] The formulations of the present disclosure may also include combinations of more than one alkylene glycol alkyl ethers. Examples of commercially available alkylene glycol alkyl ethers include, but are not limited to, FLOMIN F672®, (a blend of ca. MW 250, methyl glycol ethers), FFOMIN F660® (a blend of triethylene glycol monobutyl ether 70-80%, tetraethylene glycol monobutyl ether 15-25%, di ethylene glycol monobutyl ether <5%) and FFOMIN F661® (a mixture of triethylene glycol monoethyl ether and triethylene glycol monobutyl ether).

[0020] Examples of a nonionic surfactant include, but are not limited to, any surfactant of the

Triton X-series 4-(l,l,3,3-tetramethylbutyl)phenyl-polyethylene glycol, such as Triton X-15, Triton X-35, Triton X-45, Triton X- 100, Triton X- 102, Triton X- 114, Triton X- 165, Triton X-305, Triton X-405, Triton X-705, and of the Tergitol series 4-(nonyl)phenyl-polyethylene glycol, such as Tergitol NP-10, Tergitol NP-12, 13, Tergitol NP-15, Tergitol NP-30, Tergitol NP-4, Tergitol NP-40, Tergitol NP-50, Tergitol NP-6, Tergitol NP-7, Tergitol NP-70, Tergitol NP-8, Tergitol NP-

9, Tergitol NP-57.

[0021] Examples of a sorbitan surfactant include, but are not limited to, polyethylene glycol sorbitan monolaurate (Tween 20), polyethylene glycol sorbitan monopalmitate (Tween 40), polyethylene glycol sorbitan monostearate (Tween 60), polyoxyethylenesorbitan tristearate (Tween 65), polyethylene glycol sorbitan monooleate (Tween 80), polyoxyethylenesorbitan trioleate (Tween 85), sorbitan monolaurate (Span 20), sorbitan monopalmitate (Span 40), sorbitan monostearate (Span 60), sorbitan tristearate (Span 65), sorbitan monooleate (Span 80), sorbitan sesquioleate (Span 83), sorbitan trioleate (Span 85), and sorbitan isostearate (Span 120). [0022] Examples of a phosphate ester or a mixture of phosphate esters include, but are not limited to, poly(oxy-l,2-ethanediyl)a-butyl-co-hydroxy-phosphate, poly(oxy-l,2-ethanediyl) a- hydro-o -hydroxy-mono-Cs-io-alkyl ethers phosphates, nonylphenol ethoxylate phosphate, potassium tridecyl alcohol ethoxylate phosphate ester, polyethylene glycol monotridecyl ether phosphate, and tristyrylphenol ethoxylate phosphate ester.

[0023] Examples of an anionic surfactant include, but are not limited to, sodium 2-ethylhexyl sulfate, sodium laureth sulfate, sodium lauryl sulfate, ammonium laureth sulfate, ammonium lauryl sulfate, sodium dodecyl benzene sulfonate, sodium xylene sulfonate, and alkyldiphenyloxide disulfonates, such as those sold as DOWFAX™ 2A1 and DOWFAX™ 3B2.

[0024] In at least one embodiment, the surfactant, such as for example, Tween 20, is present in the formulations of the present disclosure, in an amount of from about 0.1% to about 15% by weight of the total weight of the formulation. The surfactant may be present in the formulations of the present disclosure in an amount ranging from about 0.10% to about 15.00% by weight, such as from about 0.10% to about 0.25%, such as from about 0.25% to about 0.50%, such as from about 0.50% to about 0.75%, such as from about 0.75% to about 1.00%, such as from about 1.00% to about 1.25%, such as from about 1.25% to about 1.50%, such as from about 1.50% to about 1.75%, such as from about 1.75% to about 2.00%, such as from about 2.00% to about 2.25%, such as from about 2.25% to about 2.50%, such as from about 2.50% to about 2.75%, such as from about 2.75% to about 3.00%, such as from about 3.00% to about 3.25%, such as from about 3.25% to about 3.50%, such as from about 3.50% to about 3.75%, such as from about 3.75% to about 4.00%, such as from about 4.00% to about 4.25%, such as from about 4.25% to about 4.50%, such as from about 4.50% to about 4.75%, such as from about 4.75% to about 5.00%, such as from about 5.00% to about 5.25%, such as from about 5.25% to about 5.50%, such as from about 5.50% to about 5.75%, such as from about 5.75% to about 6.00%, such as from about 6.00% to about 6.25%, such as from about 6.25% to about 6.50%, such as from about 6.50% to about 6.75%, such as from about 6.75% to about 7.00%, such as from about 7.00% to about 7.25%, such as from about 7.25% to about 7.50%, such as from about 7.50% to about 7.75%, such as from about 7.75% to about 8.00%, such as from about 8.00% to about 8.25%, such as from about 8.25% to about 8.50%, such as from about 8.50% to about 8.75%, such as from about 8.75% to about 9.00%, such as from about 9.00% to about 9.25%, such as from about 9.25% to about 9.50%, such as from about 9.50% to about 9.75%, such as from about 9.75% to about 10.00%, such as from about 10.00% to about 10.25%, such as from about 10.25% to about 10.50%, such as from about 10.50% to about 10.75%, such as from about 10.75% to about 11.00%, such as from about 11.00% to about

11.25%, such as from about 11.25% to about 11.50%, such as from about 11.50% to about 11.75%, such as from about 11.75% to about 12.00%, such as from about 12.00% to about 12.25%, such as from about 12.25% to about 12.50%, such as from about 12.50% to about 12.75%, such as from about 12.75% to about 13.00%, such as from about 13.00% to about 13.25%, such as from about 13.25% to about 13.50%, such as from about 13.50% to about 13.75%, such as from about 13.75% to about 14.00%, such as from about 14.00% to about 14.25%, such as from about 14.25% to about 14.50%, such as from about 14.50% to about 14.75%, such as from about 14.75% to about 15.00%.

[0025] The formulations of the present disclosure may also include a glycol or glycol derivative. Examples of glycols include, but are not limited to, ethylene glycol (commonly referred to as glycol), propylene glycol (PG) (1,2-propanediol), 1,3 -propanediol, 1 ,4-butanediol, 1,5- pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2,4-pentanediol, 2,5-hexanediol, 4,5-octanediol, and 3,4-hexanediol. Other examples of glycols include, but are not limited to, diethylene glycol and propylene glycol.

[0026] Examples of glycol derivatives include, but are not limited to, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol methyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol methyl ether acetate, ethylene glycol monostearate, ethylene glycol distearate, ethylene glycol ami do stearate, propylene glycol monostearate, propylene glycol dicaprylate, propylene glycol dicaprate diacetate glycol, dilaurate glycol, dipalmite glycol, diformate glycol, dibutyrate glycol, dibenzorate glycol, dipalmate glycol, dipropionate glycol, monoacetate glycol, monopalmitate glycol, monoformate glycol, and diethylene glycol monostearate. Examples of glycol derivatives also include, but are not limited to, C3-C12 triols and/or C3-C12 triol derivatives, including C3-C6 triols, glycerol monostearate, glycerol distearate, glycerol monooleate, glycerol monolaurate, glycerol dilaurate, glycerol dipalmitate, glycerol monopalmitate, glycerol triacetate, glycerol tribenzoate, glycerol tributyrate, glycerol trimyristate, glycerol trioleate, glycerol trilaurate, glycerol tripalmitate, and glycerol tristearate.

[0027] In at least one embodiment, the glycol or glycol derivative, such as for example, 1,2- propanediol, is present in the formulations of the present disclosure, in an amount of from about 20% to about 90% by weight of the total weight of the formulation. The glycol or glycol derivative may be present in the formulations of the present disclosure in an amount ranging from about 20% to about 90% by weight, such as from about 20% to about 85%, such as from about 20% to about 80%, such as from about 20% to about 75%, such as from about 20% to about 70%, such as from about 20% to about 65%, such as from about 20% to about 60%, such as from about 20% to about

55%, such as from about 20% to about 50%, such as from about 20% to about 45%, such as from about 20% to about 40%, such as from about 20% to about 35%, such as from about 20% to about

30%, such as from about 25% to about 90%, such as from about 30% to about 90%, such as from about 35% to about 90%, such as from about 40% to about 90%, such as from about 45% to about

90%, such as from about 50% to about 90%, such as from about 55% to about 90%, such as from about 60% to about 90%, such as from about 65% to about 90%, such as from about 70% to about 90%, such as from about 75% to about 90%, such as from about 70% to about 90%, such as from about 85% to about 90%. In at least one embodiment, the glycol or glycol derivative is present in the formulations of the present disclosure in an amount of about 21% to about 41%, such as from about 25% to about 41%, such as from about 30% to about 41%, such as from about 35% to about 41%. The glycol or glycol derivative may be present in the formulations of the present disclosure in an amount of about 20.0% to about 37.5%, such as from about 12.0% to about 37.0%, such as from about 12.5% to about 36.5%, such as from about 13.0% to about 36.0%, such as from about 13.5% to about 35.5%, such as from about 14.0% to about 35.0%, such as from about 14.5% to about 34.5%, such as from about 15.0% to about 34.0%, such as from about 15.5% to about 33.5%, such as from about 16.0% to about 33.0%, such as from about 16.5% to about 32.5%, such as from about 17.0% to about 32.0%, such as from about 18.0% to about 31.5%, such as from about 18.5% to about 31.0%, such as from about 19.0% to about 30.5%, such as from about 19.5% to about 30.0%, such as from about 20.0% to about 29.5%, such as from about 20.5% to about 29.0%, such as from about 21.0% to about 28.5%, such as from about 21.5% to about 28.0%, such as from about 22.0% to about 27.5%, such as from about 22.5% to about 27.0%, such as from about 23.0% to about 26.5%, such as from about 23.5% to about 26.0%, or from about 24.0% to about 25.5%.

[0028] The formulations of the present disclosure may also include a cyclic amide, such as NMP or N~ buty 1 py rol id one (NBP). In at least one embodiment, however, the formulation does not include a cyclic amide. In at least one embodiment, the formulation does not include NMP, i.e., it is substantially free of NMP. In at least one embodiment, the cyclic amide is present in the formulations of the present disclosure in an amount of from about 1% to about 30% by weight of the total weight of the formulation. The cyclic amide may be present in the formulations of the present disclosure in an amount ranging from about 1% to about 30% by weight, such as from about 1% to about 5%, such as from about 5% to about 10%, such as from about 10% to about 20%, such as from about 10% to about 15%. The cyclic amide may be present in the formulations of the present disclosure in a range of about 3% to about 30%, such as from about 3% to about 28%, such as from about 3% to about 26%, such as from about 3% to about 24%, such as from about 3% to about 22%, such as from about 3% to about 20%, such as from about 3% to about 18%, such as from about 3% to about 16%, such as from about 3% to about 14%, such as from about 3% to about 12%, such as from about 3% to about 10%, such as from about 3% to about 8%, such as from about 3% to about 6%, or such as from about 3% to about 4%.

[0029] In at least one embodiment, NMP is present in the formulations of the present disclosure in an amount of from about 1% to about 30% by weight of the total weight of the formulation. NMP may be present in the formulations of the present disclosure in an amount ranging from about

1% to about 30% by weight, such as from about 1% to about 5%, such as from about 5% to about 10%, such as from about 10% to about 20%, such as from about 10% to about 15%. NMP may be present in the formulations of the present disclosure in a range of about 3% to about 30%, such as from about 3% to about 28%, such as from about 3% to about 26%, such as from about 3% to about 24%, such as from about 3% to about 22%, such as from about 3% to about 20%, such as from about 3% to about 18%, such as from about 3% to about 16%, such as from about 3% to about 14%, such as from about 3% to about 12%, such as from about 3% to about 10%, such as from about 3% to about 8%, such as from about 3% to about 6%, or such as from about 3% to about 4%.

[0030] The formulations of the present disclosure may also comprise a second surfactant, such as for example, Triton X-100. The second surfactant may be present in the formulations of the present disclosure in an amount ranging from about 0.10% to about 15.00% by weight, such as from about 0.10% to about 0.25%, such as from about 0.25% to about 0.50%, such as from about 0.50% to about 0.75%, such as from about 0.75% to about 1.00%, such as from about 1.00% to about 15.00% by weight, such as from about 1.00% to about 1.25%, such as from about 1.25% to about 1.50%, such as from about 1.50% to about 1.75%, such as from about 1.75% to about 2.00%, such as from about 2.00% to about 2.25%, such as from about 2.25% to about 2.50%, such as from about 2.50% to about 2.75%, such as from about 2.75% to about 3.00%, such as from about 3.00% to about 3.25%, such as from about 3.25% to about 3.50%, such as from about 3.50% to about 3.75%, such as from about 3.75% to about 4.00%, such as from about 4.00% to about 4.25%, such as from about 4.25% to about 4.50%, such as from about 4.50% to about 4.75%, such as from about 4.75% to about 5.00%, such as from about 5.00% to about 5.25%, such as from about 5.25% to about 5.50%, such as from about 5.50% to about 5.75%, such as from about 5.75% to about 6.00%, such as from about 6.00% to about 6.25%, such as from about 6.25% to about 6.50%, such as from about 6.50% to about 6.75%, such as from about 6.75% to about 7.00%, such as from about 7.00% to about 7.25%, such as from about 7.25% to about 7.50%, such as from about 7.50% to about 7.75%, such as from about 7.75% to about 8.00%, such as from about 8.00% to about 8.25%, such as from about 8.25% to about 8.50%, such as from about 8.50% to about 8.75%, such as from about 8.75% to about 9.00%, such as from about 9.00% to about 9.25%, such as from about 9.25% to about 9.50%, such as from about 9.50% to about 9.75%, such as from about 9.75% to about 10.00%, such as from about 10.00% to about 10.25%, such as from about 10.25% to about 10.50%, such as from about 10.50% to about 10.75%, such as from about 10.75% to about 11.00%, such as from about 11.00% to about 11.25%, such as from about 11.25% to about 11.50%, such as from about 11.50% to about 11.75%, such as from about 11.75% to about 12.00%, such as from about 12.00% to about 12.25%, such as from about 12.25% to about 12.50%, such as from about 12.50% to about 12.75%, such as from about 12.75% to about 13.00%, such as from about 13.00% to about 13.25%, such as from about 13.25% to about 13.50%, such as from about 13.50% to about 13.75%, such as from about 13.75% to about 14.00%, such as from about 14.00% to about 14.25%, such as from about 14.25% to about 14.50%, such as from about 14.50% to about 14.75%, such as from about 14.75% to about 15.00%.

[0031] The formulations of the present disclosure may also comprise water. When the formulation comprises an adduct of NBPT, urea and formaldehyde alone or with NBPT but not with an additional urea source, the water may be present in an amount ranging from about 1.00% to about 20.00% by weight, such as from about 1.00% to about 1.25%, such as from about 1.25% to about 1.50%, such as from about 1.50% to about 1.75%, such as from about 1.75% to about 2.00%, such as from about 2.00% to about 2.25%, such as from about 2.25% to about 2.50%, such as from about 2.50% to about 2.75%, such as from about 2.75% to about 3.00%, such as from about 3.00% to about 3.25%, such as from about 3.25% to about 3.50%, such as from about 3.50% to about 3.75%, such as from about 3.75% to about 4.00%, such as from about 4.00% to about 4.25%, such as from about 4.25% to about 4.50%, such as from about 4.50% to about 4.75%, such as from about 4.75% to about 5.00%, such as from about 5.00% to about 5.25%, such as from about 5.25% to about 5.50%, such as from about 5.50% to about 5.75%, such as from about 5.75% to about 6.00%, such as from about 6.00% to about 6.25%, such as from about 6.25% to about 6.50%, such as from about 6.50% to about 6.75%, such as from about 6.75% to about 7.00%, such as from about 7.00% to about 7.25%, such as from about 7.25% to about 7.50%, such as from about 7.50% to about 7.75%, such as from about 7.75% to about 8.00%, such as from about 8.00% to about 8.25%, such as from about 8.25% to about 8.50%, such as from about 8.50% to about 8.75%, such as from about 8.75% to about 9.00%, such as from about 9.00% to about 9.25%, such as from about 9.25% to about 9.50%, such as from about 9.50% to about 9.75%, such as from about 9.75% to about 10.00%, such as from about 10.00% to about 10.25%, such as from about 10.25% to about 10.50%, such as from about 10.50% to about 10.75%, such as from about 10.75% to about 11.00%, such as from about 11.00% to about 11.25%, such as from about 11.25% to about 11.50%, such as from about 11.50% to about 11.75%, such as from about 11.75% to about 12.00%, such as from about 12.00% to about 12.25%, such as from about 12.25% to about 12.50%, such as from about 12.50% to about 12.75%, such as from about 12.75% to about 13.00%, such as from about 13.00% to about 13.25%, such as from about 13.25% to about 13.50%, such as from about 13.50% to about 13.75%, such as from about 13.75% to about 14.00%, such as from about 14.00% to about 14.25%, such as from about 14.25% to about 14.50%, such as from about 14.50% to about 14.75%, such as from about 14.75% to about 15.00%, such as from about 15.00% to about 15.25%, such as from about 15.25% to about 15.50%, such as from about 15.50% to about 15.75%, such as from about 15.75% to about 16.00%, such as from about 16.00% to about 16.25%, such as from about 16.25% to about 16.50%, such as from about 16.50% to about 16.75%, such as from about 16.75% to about 17.00%, such as from about 17.00% to about 17.25%, such as from about 17.25% to about 17.50%, such as from about 17.50% to about 17.75%, such as from about 17.75% to about 18.00%, such as from about 18.00% to about 18.25%, such as from about 18.25% to about 18.50%, such as from about 18.50% to about 18.75%, such as from about 18.75% to about 19.00%, such as from about 19.00% to about 19.25%, such as from about 19.25% to about 19.50%, such as from about 19.50% to about 19.75%, such as from about 19.75% to about 20.00%.

[0032] The formulations of the present disclosure may also include a dye. Examples of dyes include, but are not limited to, FD&C Blue No. 1, FD&C Blue No. 1, FD&C Green No. 3, FD&C Yellow No. 5, FD&C Red No. 3, FD&C Red No. 41, FD&C Yellow No. 6, AGROTAIN® UFTRA green dye, and a Milliken Fiquitint® dye. In at least one embodiment, the dye, such as for example, Fiquitint® dye, is present in the formulations of the present disclosure in an amount of from about 0.3% to about 10% by weight of the total weight of the formulation. The dye may be present in the formulations of the present disclosure in an amount ranging from about 0.3% to about 10%, such as from about 0.5% to about 10%, such as from about 1% to about 10%, such as from about 2% to about 10%, such as from about 3% to about 10%, such as from about 4% to about 10%, such as from about 5% to about 10%, such as from about 6% to about 10%, such as from about 7% to about 10%, such as from about 8% to about 10%, such as from about 9% to about 10%, such as from about 0.3% to about 2%, such as from about 0.5% to about 2%, such as from about 0.6% to about 2%, such as from about 0.75% to about 2%, such as from about 1% to about 2%, such as from about 1.5% to about 2%, such as from 0.3% to 1%, such as from 0.5% to 1%.

[0033] The formulations of the present disclosure may also include a defoamer. In at least one embodiment, the defoamer is present in the formulations of the present disclosure in an amount of from about 0.01% to about 5% by weight of the total weight of the formulation. The defoamer may be present in the formulations of the present disclosure in an amount ranging from about 0.01% to about 5% by weight, such as from about 0.02% to about 5%, such as from about 0.05% to about 5%, such as from about 0.1% to about 5%, such as from about 0.5% to about 5%, such as from about 1% to about 5%, such as from about 2% to about 5%, such as from about 3% to about 5%, such as from about 4% to about 5%, such as from about 0.01% to about 2%, such as from about 0.05% to about 2%, such as from about 0.1% to about 2%, such as from about 0.5% to about 2%, such as from about 1% to about 2%, such as from about 0.01% to about 1%, such as from 0.05% to 1%, such as from 0.1% to 1%, such as from 0.5% to 1%.

[0034] The formulations of the present disclosure may also include a viscosity reducer. In at least one embodiment, the viscosity reducer is present in the formulations of the present disclosure in an amount of from about 0.01% to about 5% by weight of the total weight of the formulation. The viscosity reducer may be present in the formulations of the present disclosure in an amount ranging from about 0.01% to about 5% by weight, such as from about 0.02% to about 5%, such as from about 0.05% to about 5%, such as from about 0.1% to about 5%, such as from about 0.5% to about 5%, such as from about 1% to about 5%, such as from about 2% to about 5%, such as from about 3% to about 5%, such as from about 4% to about 5%, such as from about 0.01% to about 2%, such as from about 0.05% to about 2%, such as from about 0.1% to about 2%, such as from about 0.5% to about 2%, such as from about 1% to about 2%, such as from about 0.01% to about 1%, such as from 0.05% to 1%, such as from 0.1% to 1%, such as from 0.5% to 1%.

[0035] The formulation of the present disclosure may also include one or more excipients or additives. The excipient may be a solvent, or any combination thereof. In at least one embodiment, the solvent is selected from benzyl alcohol, dimethyl sulfoxide (DMSO), morpholine, and ethoxylated amines. In some embodiments, the solvent is selected from NBP, Triethyl phosphate (TEP), Gyrene (aiso known as Dihydrolevoglueosenone), and 2-ethylhexanol (2-EH). In some embodiments, the solvent is TamiSolve xG. Examples of additives include but are not limited to: nitrification inhibitors; conditioners; xanthan gum; calcium carbonate (agricultural lime) in its various forms for adding weight and/or raising the pH of acidic soils; metal containing compounds and minerals such as gypsum, metal silicates, and chelates of various micronutrient metals such as iron, zinc and manganese; talc; elemental sulfur; activated carbon, which may act as a“safener” to protect against potentially harmful chemicals in the soil; plant protectants; nutrients; nutrient stabilizers; super absorbent polymers; wicking agents; wetting agents; plant stimulants to accelerate growth; inorganic nitrogen, phosphorus, potassium (N-P-K) type fertilizers; sources of phosphorus; sources of potassium; organic fertilizers; surfactants, such as alkylaryl poly ether alcohols; initiators; stabilizers; cross linkers; antioxidants; UV stabilizers; reducing agents; pesticides; herbicides; fungicides; plasticizers; and viscosity reducers. In some embodiments, the viscosity reducer is 2-EH. In other embodiments, the viscosity reducer is TEP. The content of the additional component(s) disclosed herein can be from about 1% to about 75% by weight of the formulation and depends, in part, on the desired function of the additional component(s) and the makeup of the composition to which the additional component(s) are added.

[0036] Examples of conditioners include, but are not limited to, tricalcium phosphate, sodium bicarbonate, sodium ferricyanide, potassium ferricyanide, bone phosphate, sodium silicate, silicon dioxide, calcium silicate, talcum powder, bentonite, calcium aluminum silicate, stearic acid, and polyacrylate powder. Examples of plant protectants and nutrient stabilizers include silicon dioxide and the like. Examples of nutrients include, but are not limited to, phosphorus and potassium- based nutrients. A commercially available fertilizer nutrient can include, for example, K-Fol 0- 40-53, which is a solution that contains 40 wt.% phosphate and 53 wt.% potassium, which is manufactured and distributed by GBS Biosciences, LLC.

[0037] Nitrification inhibitors are compounds which inhibit the conversion of ammonium to nitrate and reduce nitrogen losses in the soil. Examples of nitrification inhibitors include, but are not limited to, dicyandiamide (DCD), and the like. Although the compositions disclosed herein can include DCD, in certain embodiments, the compositions are substantially free of DCD. “Substantially free” means that either no DCD can be detected in the mixture or, if DCD can be detected, it is (1) present in <1% w/w (preferably, <0.85% w/w, <0.80% w/w, or <0.75% w/w); and (2) does not produce effects characteristic of DCD at higher proportions. For example, a composition substantially free of DCD would not produce the environmental effects of exposure to concentrated or pure DCD even if a trace amount of DCD could be detected in the mixture. Certain exemplary compositions can have a DCD content of less than about 0.85% by weight, less than about 0.80% by weight, less than about 0.75% by weight, less than about 0.5% by weight, or less than about 0.25% by weight.

[0038] The present disclosure also provides a method of making a formulation according to the present disclosure comprising: combining one or more adducts of NBPT, urea, and formaldehyde with a surfactant. NBPT and additional components may also be added, such as a glycol and/or a glycol derivative; and/or NMP; and/or one or more additives; and/or a second surfactant; and/or water; and/or a dye; and/or a defoamer; and/or a viscosity reducer.

[0039] The formulations of the present disclosure can also be used to prepare a fertilizer. For example, a formulation comprising an adduct of NBPT, urea, and formaldehyde, a surfactant, and optionally NBPT is added to a urea source and water, such as for example a solution of UAN. [0040] In one embodiment, a formulation of the present disclosure can be applied to solid urea- containing fertilizers, such as coating granular urea, added into molten urea-containing fertilizers to make incorporated urea-containing fertilizers (as described in WO2015/027244 and WO 2016/137815). The use of a surfactant in the formulations of the present disclosure improve the coating ability when blending the formulation with urea resulting in a more homogenous coating as compared to a similar formulation that does not contain the surfactant.

[0041] In a further embodiment, a formulation of the present disclosure can be applied to liquid urea- containing fertilizers. For example, a formulation according to the present disclosure can be incorporated into a homogenous water-based fertilizer formulation by blending the formulation directly with water-based media (such as a UAN solution) at ambient temperature or low temperatures, such as at 0 °C or below. Sufficient mixing is employed during this blending step to assure that formulation is homogeneously distributed throughout and that no milking or flocculation is observed. Upon standing, the fertilizer compositions of the present disclosure are stable and do not exhibit milking or flocculation at ambient or low temperatures, such as at 0 °C or below. The fertilizer compositions of the present disclosure are stable at such low temperatures for extended periods of time, including for example, during storage. In other words, the fertilizer compositions of the present disclosure remain in liquid form at low temperatures and/or for extended periods of time, such as for example, at least 2 weeks, at least one month, at least 6 months, at least one year, or at least 1.5 years.

[0042] The term“temperature of 0 °C or below” means a temperature range from about -50 °C to 0 °C. For example, in some embodiments, the fertilizer is stable at -50°C, -45°C, -40°C, -35°C, -30°C, -25°C, -20°C, -15°C, -10°C, or -5°C. In at least some embodiments, the fertilizer is stable at -15°C. [0043] Surfactants are amphiphilic molecules that concentrate at the interface between two phases and modify the properties of that interface. A list of surfactants can be found in McCutcheon's Emulsifiers & Detergents or the Industrial Surfactants Handbook. The hydrophilic- lipophilic balance (HLB) of a surfactant is measured on an empirical scale developed by Griffin (W. C. Griffin,“Classification of Surface-Active Agents by“HLB” Journal of the Society of

Cosmetic Chemists (1949), 1 : 311-326). It was found that an HLB needed to be achieved for the desired stability of the stability properties. The optimal range for the HLB of the surfactants is from about 9 to about 16.

[0044] The term“stable” means chemical and/or physical stability. Lor example, in some embodiments, stable means that no degradation is observed, no precipitate is formed, and/or the formulation does not freeze over a period of time.

[0045] The fertilizers of the present disclosure are stable meaning they exhibit substantially no milking or flocculation, at ambient temperature or at a temperature of 0 °C or below.

[0046] In at least one embodiment, the turbidity of the fertilizer composition is from about 10 NTU to about 1500 NTU. In at least one embodiment, the turbidity of the fertilizer composition is no more than 1500 NTU. In at least one embodiment, the turbidity of the fertilizer composition is no more than 170 NTU.

[0047] In one embodiment, the present disclosure provides a method to make a fertilizer composition comprising adding a formulation comprising combining one or more adducts of NBPT, urea, and formaldehyde; a surfactant; optionally NBPT; and/or; a glycol and/or a glycol derivative; and/or NMP and/or Tar SoIve NxG; and/or one or more additives; and/or a second surfactant; and/or water; and/or a dye; and/or a defoamer with water and a urea source, such as UAN solution. In at least one embodiment, about 0.1 grams to about 50.0 grams of the formulation of the present disclosure is added to about 50.0 grams to 250 grams of water-based media, such as UAN solution. In at least one embodiment, about 0.1 grams to about 0.2 grams of the formulation of the present disclosure is added to about 150.0 grams to 250 grams of a UAN solution. In at least one embodiment, about 0.173 grams of the formulation of the present disclosure is added to about 200 grams of a UAN solution. In at least one embodiment, about 1.0 grams to about 5.0 grams of the formulation of the present disclosure is added to about 50.0 grams to 150 grams of a UAN solution. In at least one embodiment, about 3.0 grams of the formulation of the present disclosure is added to about 200 grams of a UAN solution.

[0048] The present disclosure also includes methods for fertilizing soil using the disclosed fertilizer compositions. In at least one embodiment, the soil may be treated by contacting it directly with a formulation of the present disclosure. In at least one embodiment, contacting the soil with a fertilizer composition of the present disclosure may comprise administering a fertilizer composition as a spray. In at least one embodiment, contacting the soil comprises adding a fertilizer composition of the present disclosure to the irrigation water for the soil.

[0049] As will be apparent to those of skill in the art upon reading this disclosure, each of the individual embodiments described and illustrated herein has discrete components and features which may be readily separated from or combined with the features of any of the other several embodiments without departing from the scope or spirit of the present disclosure. Any recited method can be carried out in the order of events recited or in any other acceptable order. EXAMPLES

Example 1: Experiments with Tween Surfactants

[0050] “Actives” refers to one or more adducts of NBPT, formaldehyde, and urea and NBPT. The surfactant used in all entries below is a polyethylene glycol sorbitan based surfactant. The formulations are then tested for stability by dissolving 3 g of the formulation into 100 g of urea- ammonium nitrate solution. Turbidity was measured and determination of homogeneity of the solution was performed by visual inspection. In all entries in the table below, to the extent that the sum of the compositions for each entry does not equate to 100 wt%, the remainder of the formulations is water.

Example 2: Experiments with Phosphate ester- or Mixtures of Phosphate Esters-based Surfactants

[0051] “Actives” refers to one or more adducts of NBPT, formaldehyde, and urea and NBPT. The surfactant used in all entries below is a potassium salt of poly(oxy-l,2-ethanediyl), a-hydro- w-hydroxy-, mono-Cn-i4-isoalkyl ethers, Ci3-rich, phosphate (alkyl polyethoxyethanol phosphate ester) based surfactant. The formulations are then tested for stability by dissolving 0.173 g of the formulation into 200 g of urea-ammonium nitrate solution or 3 g of the formulation into 100 g of urea-ammonium nitrate solution. Turbidity was measured and determination of homogeneity of the solution was performed by visual inspection. In all entries in the tables below, to the extent that the sum of the compositions for each entry does not equate to 100 wt%, the remainder of the formulations is water.

A. At treatment dosage (0.173 g in 200 g of UAN)

B. At concentrated dosage (3 g in 100 g of UAN)

C. At concentrated dosage (3 g in 100 g of UAN) at 0 °C

D. At concentrated dosage (3 g in 100 g of UAN) at 0 °C with a defoamer

Example 3: Experiments with Mixed Surfactants

[0052] “Actives” refers to one or more adducts of NBPT, formaldehyde, and urea and NBPT. The formulations are then tested for stability by dissolving 0.173 g of the formulation into 200 g of urea-ammonium nitrate solution. The determination of homogeneity of the solution was performed by visual inspection. In all entries in the table below, to the extent that the sum of the compositions for each entry does not equate to 100 wt%, the remainder of the formulations is water. In all entries in the table below, to the extent that the sum of the compositions for each entry does not equate to 100 wt%, the remainder of the formulations is water.

Example 5: Experiments at Lower Concentration of Actives

[0053] “Actives” refers to one or more adducts of NBPT, formaldehyde, and urea and NBPT. The formulations are then tested for stability by dissolving 0.173 g of the formulation into 200 g of urea-ammonium nitrate solution. The determination of homogeneity of the solution was performed by visual inspection. In all entries in the table below, to the extent that the sum of the compositions for each entry does not equate to 100 wt%, the remainder of the formulations is water.

Claims

WE CLAIM:

1. A formulation comprising:

i) an adduct of A-(/i-butyl)thiophosphoric triamide (NBPT), urea, and formaldehyde; and ii) a surfactant.

2. A formulation comprising:

i) an adduct of NBPT, urea, and formaldehyde;

ii) NBPT; and

iii) a surfactant; and

iv) optionally one or more additives.

3. A formulation comprising:

ii) an adduct of NBPT, urea, and formaldehyde; and ii) NBPT in a combined amount ranging from about 15% to about 70% by weight of the total formulation;

vii) a surfactant in an amount ranging from about 0.1% to about 15% by weight;

viii) a glycol and/or a glycol derivative in an amount ranging from about 20% to about 90% by weight;

ix) optionally a cyclic amide in an amount ranging from about 1% to about 30% by weight; and

x) optionally one or more additives;

wherein each component is present in an amount by weight of the total formulation.

4. The formulation of claim 1, wherein an adduct of NBPT, urea, and formaldehyde is present in an amount ranging from about 15% to about 70% by weight of the total formulation.

5. The formulation of claim 2, wherein NBPT and an adduct of NBPT, urea, and formaldehyde are present in a combined amount ranging from about 15% to about 70% by weight of the total formulation.

6. The formulation of claims 1 or 2, wherein a surfactant is present in an amount ranging from about 0.1% to about 15% by weight of the total formulation.

7. The formulation of any of claims 1-3, further comprising a second surfactant in an amount ranging from about 0.1% to about 15% by weight.

8. The formulation of any of claims 1-3, further comprising water in an amount ranging from about 1% to about 20% by weight.

9. The formulation of any of claims 1-3, further comprising a dye in an amount ranging from about 0.3% to about 10% by weight.

10. The formulation of any of claims 1-3, further comprising a defoamer in an amount ranging from about 0.01% to about 5% by weight.

11. The formulation of any of claims 1-3, further comprising a viscosity reducer in an amount ranging from about 0.01% to about 5% by weight.

12. The formulation of any of claims 1-3, wherein an adduct of NBPT, urea, and formaldehyde is represented by the following structures:

Adduct III Adduct IV

13. The formulation of claim 3, wherein the glycol or glycol derivative or alkylene glycol alkyl ether is propylene glycol.

14. The formulation of any of claims 1-3, wherein the surfactant is an alkylene glycol alkyl ether selected from diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monopentyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monopentyl ether, triethylene glycol

monoisopropyl ether, triethylene glycol monoisobutyl ether, triethylene glycol monohexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monopentyl ether, tetraethylene glycol monoisopropyl ether, tetraethylene glycol monoisobutyl ether, tetraethylene glycol monohexyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopentyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol monohexyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monopentyl ether, tripropylene glycol monoisopropyl ether, tripropylene glycol monoisobutyl ether, tripropylene glycol monohexyl ether, and combinations thereof.

15. The formulation of any of claims 1-3, wherein the surfactant is an alkylene glycol alkyl ether is a mixture of triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether.

16. The formulation of claim 15, wherein the mixture of tri ethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether alkylene glycol alkyl ether contains 70-80% triethylene glycol monobutyl ether, 15-25% tetraethylene glycol monobutyl ether, and less than 5% diethylene glycol monobutyl ether.

17. The formulation of any of claims 1-3, wherein the surfactant is an alkylene glycol alkyl ether is a mixture of triethylene glycol monoethyl ether and triethylene glycol monobutyl ether.

18. The formulation of any of claims 1-3, wherein the surfactant is a nonionic surfactant.

19. The formulation of claim 18, wherein the nonionic surfactant is selected from 4-(l, 1,3,3- tetramethylbutyl)phenyl-polyethylene glycol, 4-(nonyl)phenyl-polyethylene glycol, and combinations thereof.

20. The formulation of any of claims 1-3, wherein the surfactant is a sorbitan surfactant.

21. The formulation of claim 20, wherein the sorbitan surfactant is selected from polyethylene glycol sorbitan monolaurate, polyethylene glycol sorbitan monopalmitate, polyethylene glycol sorbitan monostearate, polyoxyethylenesorbitan tristearate, polyethylene glycol sorbitan monooleate, polyoxyethylenesorbitan trioleate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan tristearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan isostearate, and combinations thereof.

22. The formulation of any of claims 1-3, wherein the surfactant is a phosphate ester or a mixture of phosphate esters.

23. The formulation of claim 22, wherein the phosphate ester or a mixture of phosphate esters is selected from poly(oxy-l,2-ethanediyl)a-butyl-co-hydroxy-phosphate, poly(oxy- 1 ,2- ethanediyl) a-hydro-co-hydroxy- mono-Cs-io-alkyl ethers phosphates, nonylphenol ethoxylate phosphate, potassium tridecyl alcohol ethoxylate phosphate ester, polyethylene glycol monotridecyl ether phosphate, tristyrylphenol ethoxylate phosphate ester, and combinations thereof.

24. The formulation of any of claims 1-3, wherein the surfactant is an anionic surfactant.

25. The formulation of claim 24, wherein the anionic surfactant is selected from sodium 2- ethylhexyl sulfate, sodium laureth sulfate, sodium lauryl sulfate, ammonium laureth sulfate, ammonium lauryl sulfate, sodium dodecyl benzene sulfonate, sodium xylene sulfonate, alkyldiphenyloxide disulfonate, and combinations thereof.

26. The formulation of claim 7, wherein the surfactant is an alkylene glycol alkyl ether and the second surfactant is a nonionic surfactant.

27. The formulation of claim 7, wherein the surfactant is an alkylene glycol alkyl ether and the second surfactant is a sorbitan surfactant.

28. The formulation of claim 7, wherein the surfactant is an alkylene glycol alkyl ether and the second surfactant is a phosphate ester or a mixture of phosphate esters.

29. The formulation of claim 7, wherein the surfactant is an alkylene glycol alkyl ether and the second surfactant is an anionic surfactant.

30. The formulation of claim 7, wherein the surfactant is a nonionic surfactant and the second surfactant is a sorbitan surfactant.

31. The formulation of claim 7, wherein the surfactant is a nonionic surfactant and the second surfactant is a phosphate ester or a mixture of phosphate esters.

32. The formulation of claim 7, wherein the surfactant is a nonionic surfactant and the second surfactant is an anionic surfactant.

33. The formulation of claim 7, wherein the surfactant is a sorbitan surfactant and the second surfactant is a phosphate ester or a mixture of phosphate esters.

34. The formulation of claim 7, wherein the surfactant is a sorbitan surfactant and the second surfactant is an anionic surfactant.

35. The formulation of claim 7, wherein the surfactant is a phosphate ester or a mixture of

phosphate esters and the second surfactant is an anionic surfactant.

36. The formulation of claim 11, wherein the viscosity reducer is 2-ethylhexanol or triethyl phosphate.

37. A fertilizer, comprising a formulation of any one of claims 1-36; a urea source; and water.

38. The fertilizer of claim 37, wherein the urea source is urea ammonium nitrate (UAN).

39. A fertilizer, comprising a formulation of any one of claims 1-36 in an amount of about 0.1 grams to about 0.2 grams and about 150 grams to about 250 grams of a UAN solution.

40. The fertilizer of any one of claims 38 or 39, wherein the turbidity of the fertilizer is not

greater than 170 NTU.

41. A fertilizer, comprising a formulation of any one of claims 1-36 in an amount of about 1 gram to about 5 grams and about 50 grams to about 150 grams of a UAN solution.

42. The fertilizer of claim 41, wherein the turbidity of the fertilizer is not greater than 1500 NTU.

43. The fertilizer of any one of claims 37-42, wherein the fertilizer is stable at 25 °C.

44. The fertilizer of any one of claims 37-42, wherein the fertilizer is stable for 2 weeks.

45. The fertilizer of any one of claims 37-42, wherein substantially no flocculation or milking of the fertilizer is observed.

46. The fertilizer of any one of claims 37-42, wherein the formulation is stable at 0 °C.

47. The fertilizer of any one of claims 37-42, wherein the fertilizer is stable for 2 weeks.

48. The fertilizer of any one of claims 37-42, wherein substantially no flocculation or milking of the fertilizer is observed.

49. The fertilizer of any one of claims 37-42, wherein the fertilizer is stable at -50 °C.

50. The fertilizer of any one of claims 37-42, wherein the fertilizer is stable for 2 weeks.

51. The fertilizer of any one of claims 37-42, wherein substantially no flocculation or milking of the fertilizer is observed.

52. A method of making a formulation according to claim 1 , comprising an adduct of NBPT, urea, and formaldehyde and a surfactant.

53. A method of making a formulation according to claim 2, comprising mixing NBPT; an

adduct of NBPT, urea, and formaldehyde; a surfactant; and optionally one or more additives.

54. A method of making a formulation according to claim 3, comprising mixing NBPT; an

adduct of NBPT, urea, and formaldehyde; a surfactant; a glycol or glycol derivative; a cyclic amide; water; a defoamer; a dye; and optionally one or more additives.

55. A method of making a urea-containing fertilizer comprising mixing the formulation

according to any one of claims 1-36 with a urea source and water.

56. A method of fertilizing soil, comprising contacting soil with a fertilizer according to any one of claims 37-42.

57. The method of claim 56, wherein the fertilizer is sprayed onto the soil.

58. The method of claim 56, wherein the fertilizer is added to the irrigation water of the soil.