Formulation system for compositions to enhance nitrogen stabilizers

Abstract

The presently disclosed subject matter is directed to formulations of nitrogen-stabilized compositions containing a nitrogen stabilizer component and an organic acid anhydride component, along with an aprotic solvent and an amine stabilizer. The formulations disclosed herein exhibit many beneficial properties, such as increased solubility of the individual components at high concentrations and increased chemical and thermal stability of the formulation.

Description

[Technical Field]

[0001] The subject matter of this disclosure is compositions and formulations thereof containing nitrogen stabilizers and organic acid anhydrides. Further descriptions of these compositions and formulations in agriculture for increasing nutrient uptake and inhibiting nitrification and / or urease activity are provided. [Background technology]

[0002] Nitrogen is an essential plant nutrient considered important for healthy and strong leaves. Urea is a major nitrogen fertilizer, providing a large nitrogen content. In the presence of soil moisture, natural or synthetic urea is converted to ammonium ions, which are then available for uptake by plants. Ammonium can be further converted to nitrates through the nitrification process by bacteria in the soil. Nitrates are also available for uptake by plants. However, the efficiency of urea utilization by plants is low.

[0003] In practice, nitrogen fertilizers are often applied only once, at the beginning of the growing season. Typically, nitrogen fertilizers are formulated as dry granules, prilli, or as a fluid consisting of urea alone, or mixed with ammonium nitrate, such as UAN (a mixture containing urea, ammonium nitrate, and water). Urea is also present in animal manure. These forms of urea have a major drawback: they decompose rapidly when applied to soil, producing ammonia gas. This is because the urease enzyme in the soil reacts with urea to produce ammonium bicarbonate and ammonia. This general series of processes is known in the art as volatilization. Volatilization results in reduced nitrogen fertilizer utilization efficiency, lower yields, nitrogen deficiency plant symptoms, undesirable odors, and potentially harmful ammonia gas concentrations. In addition, the ammonia produced can also be converted to nitrates by bacteria in the soil, a process called nitrification. Excess nitrates can be converted to nitric oxide or nitrous oxide by certain types of bacteria in the soil, a process called denitrification.

[0004] Nitrification and / or urease inhibitors (often referred to as nitrogen stabilizers) have been developed that can delay the decomposition of nitrogen fertilizers, thereby reducing the loss of nitrogen decomposition products that would otherwise occur in the absence of these inhibitors. The use of nitrification and / or urease inhibitors in combination with nitrogen fertilizers tends to increase the amount of time that nitrogen sources remain in the soil and are available for absorption by plants, in turn increasing the effectiveness of the fertilizer and positively impacting crop yield and quality. However, issues related to cost, safety, convenience, and stability limit the use of these types of inhibitors. For example, current products contain expensive organic solvents and have a low percentage of inhibitor in their composition in liquid formulations. This necessitates the application of larger percentages of these liquid dispersions, thus making their use uneconomical and inefficient. Examples of such products include, for example, Eco Agro Resources' NEON® product family, where NBPT and DCD are formulated at low concentrations in organic solvents.

[0005] Specifically, commercially available agricultural products containing combinations of NBPT and DCD exhibit various drawbacks. Their low solubility in aqueous solvents and many organic solvents has made it difficult to provide formulations containing high concentrations of NBPT and DCD, and this remains an area for improvement. Current commercially available agricultural formulations contain large amounts of organic solvents to properly formulate NBPT and DCD. These formulations often use organic solvents that exhibit undesirable odors (such as dimethyl sulfoxide), making them unsuitable for use in the field and difficult to handle. Furthermore, formulations of these products containing high amounts of organic solvents have also been shown to have adverse effects on the environment and wildlife.

[0006] Therefore, it would be highly desirable to find an economical delivery formulation that is safe for the environment and animals and contains an appropriate balance and concentration of nitrification and urease inhibitors that can be directly applied to liquid fertilizers (such as UAN). Thus, despite ongoing research efforts to improve existing products, there remains a great need in the art for the development of better compositions and formulations containing nitrogen stabilizers to efficiently control enzyme-induced urea degradation. [Overview of the Initiative]

[0007] In one embodiment, the subject matter described herein relates to a nitrogen-stabilizing composition comprising a nitrogen-stabilizing composition comprising a nitrogen-stabilizing component and an organic acid anhydride component, wherein the nitrogen-stabilizing component is a urease inhibitor and / or nitrification inhibitor; an aprotic solvent; and an amine stabilizer. In some embodiments, the nitrogen-stabilizing component is N-(n-butyl)thiophosphate triamide (NBPT) and / or dicyanamide (DCD). In some embodiments, the organic acid anhydride component is an organic acid anhydride polymer. In some embodiments, the aprotic solvent is DMSO. In some embodiments, the amine stabilizer is monomethanolamine.

[0008] Another embodiment relates to agricultural compositions comprising stabilizing agents and fertilizers disclosed herein.

[0009] Another aspect relates to a method for inhibiting soil-borne urease enzymes, comprising the step of applying a stabilized formulation disclosed herein to soil, wherein the formulation is present in an amount sufficient to inhibit the decomposition of urea by the action of soil-borne urease enzymes.

[0010] Another aspect relates to a method for soil fertilization, comprising the step of applying a stabilizing agent or agricultural composition disclosed herein to the soil.

[0011] Another embodiment relates to a method for preparing a stabilized formulation disclosed herein, comprising the steps of: mixing organic acid anhydride components with a first aprotic solvent to form a premixed organic acid anhydride component solution; taking aliquots of the premixed organic acid anhydride component solution; diluting the taken aliquots with a second aprotic solvent to obtain an organic acid anhydride solution; contacting the organic acid anhydride solution with an amine stabilizer to obtain a stabilized organic acid anhydride solution; and adding nitrogen stabilizer components to the stabilized organic acid anhydride solution to obtain a desired stabilized formulation.

[0012] These and other aspects will be described in more detail below. [Brief explanation of the drawing]

[0013] [Figure 1] The results of a field study in which cornfields were treated with no urea, urea-containing fertilizer, and the urea-containing fertilizer formulation disclosed herein (having 15% w / w NBPT, 5% w / w DCD, and 5% w / w organic acid anhydride polymer 6, based on the total weight of the formulation) are shown. Panel A of Figure 1 shows untreated corn cobs (corn cobs on the left), corn cobs treated with nitrogen fertilizer urea (corn cobs in the center), and corn cobs treated with the formulation 15-5-5 disclosed herein in combination with urea (corn cobs on the right). The number of rows in each corn cob increases from untreated corn cob > urea-treated corn cob > urea / formulation-treated corn cob. Panel B of Figure 1 shows untreated corn cobs (corn cobs on the left), corn cobs treated with nitrogen fertilizer urea (corn cobs in the center), and corn cobs treated with urea in combination with the disclosed formulation 15-5-5 (corn cobs on the right). The number of grain rows in each corn cob increases from untreated corn cob > urea-treated corn cob > urea / formulation-treated corn cob. [Figure 2]A bar graph showing the harvest results of a field study using nitrogen fertilizers in combination with the disclosed formulations on corn plants grown under no-till conditions. Different treatments (P1 - P9) were not carried out and were compared to untreated plants or plants treated with the nitrogen fertilizer urea. [Figure 3] A figure showing the untreated corn ear axis on the left and the corn ear axis treated with the nitrogen fertilizer urea (135 kg / ha of N) on the right. The untreated corn ear axis shows that insufficient supply of N leads to grain deformities (failures), while the treated corn ear axis shows an increased amount of grains. [Figure 4] A figure showing the untreated corn ear axis on the left and the corn ear axis treated with the formulation disclosed herein in combination with the nitrogen fertilizer urea (135 kg / ha of N) on the right. The untreated corn shows that insufficient supply of N leads to grain deformities (failures), while the treated corn ear axis shows that the protein level in the plant, which is the cause of grain formation and filling, is maintained by sufficient supply of N throughout the growth cycle. [Figure 5] A figure showing a corn ear axis treated with the nitrogen fertilizer urea in combination with the formulation (P) disclosed herein (refer to the left corn ear axis), an untreated corn ear axis (refer to the middle corn ear axis), and a corn ear axis treated with the nitrogen fertilizer urea (refer to the right corn ear axis). The corn ear axis treated with the formulation disclosed herein in combination with the nitrogen fertilizer urea showed the most rows of corn on the ear axis. [Figure 6] A figure showing a corn ear axis treated with the nitrogen fertilizer urea in combination with the formulation (P) disclosed herein (refer to the left corn ear axis), and a corn ear axis treated with the nitrogen fertilizer urea (refer to the right corn ear axis). The corn ear axis treated with the formulation disclosed herein in combination with the nitrogen fertilizer urea showed the most rows of corn on the ear axis.

Mode for Carrying Out the Invention

[0014] Here, the subject matter of the present disclosure will be described more fully below. However, those skilled in the art related to the subject matter of the present disclosure who benefit from the teachings presented in the foregoing description will envision many variations and other embodiments of the subject matter of the present disclosure described herein. Accordingly, it is to be understood that the subject matter of the present disclosure is not limited to the specific embodiments disclosed, and that variations and other embodiments are intended to be included within the scope of the appended claims. In other words, the subject matter described herein encompasses all alternatives, variations, and equivalents. Without limitation, if one or more of the incorporated documents, patents, and similar materials, including defined terms, use of terms, described techniques, etc., are different from or conflict with the present application, the present application shall prevail. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this belongs. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety.

[0015] As described above, urea is one of the major nitrogen fertilizers widely used in agricultural production. Up to 40% of the nitrogen applied as urea can be lost if misapplied, because it can react with water via the urease enzyme to form ammonium carbonate after being applied in the field. Ammonium carbonate is unstable and can decompose into carbon dioxide and ammonia and volatilize into the air and be lost. The loss can be substantial and depends on many factors such as soil pH, soil temperature, soil moisture, the soil's cation exchange capacity, and soil organic matter content.

[0016] Numerous methods have been developed or proposed to control volatile nitrogen loss from urea, including the application of copper and zinc metal salts, boron compounds, organic urease inhibitors, acid coatings, polymer coatings, and reactions with urea aldehydes to form reaction adducts. For example, N-(butyl)thiophosphate triamide (NBPT) is one of the most well-known urease inhibitors in agriculture worldwide. Unfortunately, NBPT faces various drawbacks in its use. For instance, NBPT is a sticky, waxy, heat and water-sensitive material that cannot be used in solid form, making it very difficult to handle, and because it is used at low concentrations, it is difficult to distribute uniformly on solid urea-containing compositions, such as prills (i.e., large granules) and in soil. To distribute NBPT evenly on solid urea-containing compositions, it is necessary to disperse NBPT in a carrier before spraying it onto the solid urea-containing composition. Therefore, the use of a solvent system containing NBPT is desirable because the solvent system can distribute NBPT in its liquid form into granular urea (e.g., urea prill) and liquid fertilizers containing urea. By introducing NBPT into the liquid fertilizer containing urea (e.g., urea-ammonium nitrate solution or UAN) in the solvent system, NBPT is more completely dispersed in the liquid fertilizer. However, NBPT is thermally unstable and decomposes upon contact with water and acid. This is particularly observed in agricultural fields (e.g., cornfields, wheatfields, etc.), where temperatures often exceed 35°C, and sometimes even reach over 45°C. Once decomposed, NBPT is not effective in providing the desired inhibitory effect on urease enzymes. Therefore, formulations that reduce the loss and decomposition rate of NBPT would be very valuable, as they could thereby improve its effectiveness in soil and reduce the negative environmental impact of the compound itself.

[0017] Dicyandiamide is a nitrification inhibitor often used in aqueous agricultural applications, such as in end-use fertilizer compositions. Like urease inhibitors, dicyandiamide has several drawbacks. Nitrification inhibitors such as dicyandiamide generally have very low water solubility (approximately 41 g / liter ("g / l")). Therefore, introducing nitrification inhibitors into aqueous end-use fertilizer compositions is difficult, especially under field conditions. As a result, nitrification inhibitors such as dicyandiamide are used at low concentrations in water, which makes it difficult to evenly distribute the nitrification inhibitor onto solid urea-containing compositions such as prill (i.e., large granules) and into the soil. To uniformly distribute dicyandiamide onto urea-containing prill or granules, the dicyandiamide needs to be dispersed on a solvent carrier before being sprayed onto the urea. Therefore, the use of a solvent system containing dicyandiamide (also referred to herein as "DCD") is desirable because the solvent system can distribute dicyandiamide in liquid form to urea granules or prilli, urea ammonium nitrate granules or prilli, or otherwise urea-containing granules or prilli, and to liquid fertilizers containing urea or urea ammonium nitrate. By introducing dicyandiamide into a liquid fertilizer containing urea in the solvent system (e.g., urea ammonium nitrate solution or UAN), DCD can be better dispersed in the liquid fertilizer.

[0018] Advantageously, the compositions, formulations, and methods described herein have been shown to provide desirable properties for the use of nitrogen stabilizers such as NBPT and / or DCD in agriculture by formulating these nitrogen stabilizers together with organic acid anhydrides in the specific solvent systems disclosed herein. Combining these nitrogen stabilizers with organic acid anhydrides in the disclosed solvent systems (also referred to as "vehicles") provides formulations exhibiting a variety of beneficial properties, including, but not limited to, extended thermal / chemical / enzymatic stability, increased shelf life, reduced volatility, reduced application rate, improved viscosity, absence of any strong or undesirable odors or smells, ease of preparation, ease of handling, extended / longer-lasting urease and nitrification inhibitory effects, and excellent environmental and toxicological profiles.

[0019] While not bound by theory, it is believed that organic acid anhydrides provide a stabilizing effect to nitrogen stabilizers, thereby improving their thermal, chemical, and / or enzymatic stability, and consequently reducing the degradation of the nitrogen stabilizers. Furthermore, the vehicle disclosed herein enables solvation of nitrogen stabilizers and organic acid anhydrides at high concentrations. This provides a formulation that exhibits improved thermal and chemical stability, reduced odor, and additional beneficial properties compared to currently available nitrogen stabilizer formulations.

[0020] Therefore, the compositions and formulations disclosed herein not only contribute to increasing the availability of nitrogen stabilizers but also to extending the lifespan of their performance as efficient nitrogen stabilizers.

[0021] definition As used herein, the term “heteroaryl” refers to a radical containing at least five or six unsaturated and conjugated aromatic rings, comprising at least two ring carbon atoms and one to four ring heteroatoms selected from nitrogen, oxygen, and / or sulfur. Such heteroaryl radicals are often alternatively referred to as “heteroaromatic” by those skilled in the art. In some examples, heteroaryl radicals have two to twelve carbon atoms, or alternatively four to five carbon atoms, within the heteroaryl ring. Examples include, but are not limited to, pyridinyl, pyrimidinyl, pyrazinyl, pyrrolyl, furanyl, tetrazolyl, isoxazolyl, oxadiazolyl, benzothiophenyl, benzofuranyl, quinolinyl, and isoquinolinyl.

[0022] As used herein, the term “aryl” refers to a radical comprising at least one unsaturated and conjugated six-membered ring, similar to the six-membered ring of benzene. Such aryl radicals having unsaturated and conjugated rings are also known to those skilled in the art as “aromatic” radicals. In some embodiments, aryl radicals have 6 to 12 ring carbons. Examples of aryl radicals include, but are not limited to, aromatic radicals such as phenyl and naphthyl cyclic radicals.

[0023] As used herein, the term “substituted” refers to a moiety (such as a heteroaryl, aryl, alkyl, and / or alkenyl) that is bonded to one or more additional organic or inorganic substituent radicals. In some embodiments, the substituted moiety includes one, two, three, four, or five additional substituents or radicals. Preferred organic and inorganic substituent radicals include, but are not limited to, hydroxyl, cycloalkyl, aryl, substituted aryl, heteroaryl, heterocyclic ring, substituted heterocyclic ring, amino, monosubstituted amino, disubstituted amino, acyloxy, nitro, cyano, carboxy, carboalkoxy, alkylcarboxamide, substituted alkylcarboxamide, dialkylcarboxamide, substituted dialkylcarboxamide, alkylsulfonyl, alkylsulfinyl, thioalkyl, alkoxy, substituted alkoxy, or haloalkoxy radicals, the terms as defined herein. Unless otherwise indicated herein, organic substituents may contain one to four or five to eight carbon atoms. If the substituted portion is bonded to two or more substituent radicals, the substituent radicals may be the same or different.

[0024] As used herein, the term “unsubstituted” means a moiety (such as heteroaryl, aryl, alkenyl, and / or alkyl) that is not bonded to one or more additional organic or inorganic substituent radicals as described above, and that such moiety is substituted only with hydrogen.

[0025] As used herein, the terms “halo,” “halogen,” or “halide” refer to atoms or ions of fluorine, chlorine, bromine, or iodine.

[0026] As used herein, the term "alkoxy" refers to an alkyl radical linked via a single terminal ether linkage; that is, the "alkoxy" group may be defined as -OR, where R is the alkyl group as defined above. Examples include, but are not limited to, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, t-butoxy, and iso-butoxy.

[0027] As used herein, the term “substituted alkoxy” refers to the alkoxy radical as defined above, having one, two, or more additional organic or inorganic substituent radicals bonded to an alkyl radical. Suitable organic and inorganic substituent radicals include, but are not limited to, hydroxyl, cycloalkyl, amino, monosubstituted amino, disubstituted amino, acyloxy, nitro, cyano, carboxy, carboalkoxy, alkylcarboxamide, substituted alkylcarboxamide, dialkylcarboxamide, substituted dialkylcarboxamide, alkylsulfonyl, alkylsulfinyl, thioalkyl, thiohaloalkyl, alkoxy, substituted alkoxy, or haloalkoxy. If the alkyl of the alkoxy is bonded to two or more substituent radicals, the substituent radicals may be the same or different.

[0028] As used herein, the term "amino" refers to a substituted or unsubstituted trivalent nitrogen-containing radical or group that is structurally related to ammonia (NH3) by the substitution of one or more hydrogen atoms of ammonia by a substituted radical.

[0029] As used herein, the term "monosubstituted amino" means an amino acid substituted with one radical selected from alkyl, substituted alkyl, or arylalkyl, and the term has the same definition as found herein.

[0030] As used herein, the term “disubstituted amino” means an amino acid that can be substituted with two identical or different radicals selected from aryl, substituted aryl, alkyl, substituted alkyl, or arylalkyl, and these terms have the same definitions as disclosed herein. Examples include, but are not limited to, dimethylamino, methylethylamino, and diethylamino. The two substituted radicals present may be the same or different.

[0031] As used herein, the term "haloalkyl" refers to the alkyl radical as defined above, which is substituted with one or more halogens, such as fluorine, chlorine, bromine, or iodine. Examples include, but are not limited to, trifluoromethyl and pentafluoroethyl.

[0032] As used herein, the term "haloalkoxy" refers to the haloalkyl group defined above, which directly bonds to oxygen to form trifluoromethoxy, pentafluoroethoxy, and the like.

[0033] As used herein, the term "acyl" refers to a radical containing a carbonyl (-C(O)-R group), where the R group is either hydrogen or has 1 to 8 carbon atoms. Examples, but not limited to, include formyl, acetyl, propionyl, butanoyl, isobutanoyl, pentanoyl, hexanoyl, heptanoyl, and benzoyl.

[0034] As used herein, the term "acyloxy" refers to a radical containing a carboxyl (-OC(O)-R) group, where the R group is either hydrogen or contains 1 to 8 carbon atoms. Examples include, but are not limited to, acetyloxy, propionyloxy, butanoyloxy, isobutanoyloxy, and benzoyloxy.

[0035] As used herein, the term “alkyl group” refers to a saturated hydrocarbon radical containing 1 to 8, 1 to 6, 1 to 4, or 5 to 8 carbon atoms. In some examples, alkyl groups refer to saturated hydrocarbon radicals containing more than 8 carbon atoms. Alkyl groups are structurally similar to acyclic alkane compounds, modified by removing one hydrogen atom from an acyclic alkane and thereby substituting it with a non-hydrogen group or radical. Alkyl group radicals can be branched or unbranched. Lower alkyl group radicals have 1 to 4 carbon atoms. Higher alkyl group radicals have 5 to 8 carbon atoms. Examples of alkyl, lower alkyl, and higher alkyl group radicals include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, amyl, t-amyl, n-pentyl, n-hexyl, i-octyl, and others.

[0036] As used herein, the term “alkenyl group” refers to an unsaturated hydrocarbon radical containing 2 to 8, 2 to 6, 2 to 4, or 5 to 8 carbon atoms and at least one carbon-carbon double bond. In some examples, an alkenyl group refers to an unsaturated hydrocarbon radical containing more than 8 carbon atoms. An unsaturated hydrocarbon radical is similar to an alkyl radical as defined above, and it also contains at least one carbon-carbon double bond. Examples include, but are not limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexanyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, etc. The term “alkenyl” includes linear and branched dienes and trienes.

[0037] As used herein, the term "monocyclic" refers to a molecular structure containing a single ring of atoms, such as benzene or cyclopropane.

[0038] As used herein, the term “bicyclic” refers to a molecular structure that contains a ring of two atoms condensed together, such as naphthalene.

[0039] As used herein, the term “tricyclic” refers to a molecular structure that contains a ring of three atoms condensed together.

[0040] As used herein, “nitrogen stabilizer” means any substance or mixture of substances intended to prevent or inhibit processes of nitrification, denitrification, ammonia volatilization, or urease production mediated by soil bacteria.

[0041] As used herein, “nitrification inhibitor” refers to the property of a compound that inhibits the oxidation of ammonia to nitrite / nitrate.

[0042] As used herein, the term “urease inhibitor” refers to the property of a compound to inhibit the activity of the urease enzyme. Inhibition may be quantified as described elsewhere herein.

[0043] As used herein, the term “thermal stability” refers to the stability of a substance when exposed to a thermal stimulus over a given period of time. Examples of thermal stimuli include, but are not limited to, heat generated from an electrical source and / or heat generated from the sun.

[0044] As used herein, the term “chemical stability” refers to the resistance of a substance to structural changes when exposed to external factors such as air (which can cause oxidation), light (e.g., sunlight), moisture / humidity (from water), heat (from the sun), and / or chemical agents. Exemplary chemical agents include, but are not limited to, any organic or inorganic substances that may degrade the structural integrity of the compound of interest (e.g., the disclosed polyanionic polymer).

[0045] As used herein, the term “enzymatic stability” refers to the resistance of a substance (e.g., the disclosed anionic polymer) to external biological organisms that disrupt its structural stability. Exemplary biological organisms include, but are not limited to, bacteria and microorganisms present in soil.

[0046] As used herein, the term “effective amount” refers to the amount of nitrogen stabilizing composition and / or the amount of each component in the stabilizing composition (i.e., nitrogen stabilizer components and / or organic acid anhydride components) that is sufficient to achieve nitrification inhibition and / or urease inhibition as described below. More exemplary information regarding the amount used, application method, and preferred ratio is given below. Those skilled in the art will be well aware that such amounts can vary over a wide range and depend on various factors, such as weather, target species, locus, application method, soil type, treated cultivated plants or materials, and climatic conditions.

[0047] As used herein, the term “soil” should be understood as a natural body consisting of living organisms (e.g., microorganisms (bacteria and fungi, etc.), animals and plants) and non-living matter (e.g., minerals and organic matter (e.g., organic compounds of varying degrees of decomposition), liquids and gases) that arise on the land surface, characterized by soil strata distinguishable from the original material as a result of various physical, chemical, biological, and anthropogenic processes. From an agricultural perspective, soil is primarily considered the anchorage and base of major nutrients for plants (plant habitat).

[0048] As used herein, the term “fertilizer” should be understood as a compound applied to promote the growth of plants and fruits. Fertilizers are typically applied either through the soil (for uptake by plant roots) or through supply to the leaves (for uptake through leaves). The term “fertilizer” can be subdivided into two main categories: a) organic fertilizers (consisting of decaying plant / animal matter) and b) inorganic fertilizers (consisting of chemicals and minerals). Examples of organic fertilizers include manure, slurry, earthworm castings, peat, seaweed, sewage, and guano. Green manure crops are also regularly cultivated to add nutrients (especially nitrogen) to the soil. Examples of manufactured organic fertilizers include compost, blood meal, bone meal, and seaweed extracts. Further examples include enzymatically digested proteins, fish meal, and feather meal. Decomposing crop residues from several years ago is another source of fertilization. Naturally occurring minerals such as phosphate rock, potassium sulfate, and limestone are also considered inorganic fertilizers. Inorganic fertilizers are typically produced through chemical processes (e.g., the Haber-Bosch process) and by chemically modifying naturally occurring sediments (e.g., concentrated triple superphosphates). Naturally occurring inorganic fertilizers include Chilean sodium nitrate, phosphate rock, and limestone.

[0049] As used herein, the term “manure” should be understood as organic matter used as organic fertilizer in agriculture. Depending on its structure, manure can be classified into liquid manure, semi-liquid manure, solid or solid manure, and straw manure. Depending on its origin, manure can be classified into animal or plant-derived manure. Common forms of animal manure include feces, urine, farm slurry (liquid manure), or compost (FYM), although FYM also includes certain amounts of plant material (typically straw) that may be used as animal bedding. Animals that can be used as sources of manure include horses, cattle, pigs, sheep, chickens, turkeys, rabbits, and guano derived from seabirds and bats. The amount of animal manure applied when used as fertilizer depends largely on the source (type of animal). Plant manure can be derived from all kinds of plants, but the plants may be explicitly cultivated for the purpose of tilling (e.g., legumes), thus improving soil structure and fertility. Furthermore, plant matter used as manure may include the contents of the rumen of slaughtered ruminants, used hops (leftover from beer brewing), or seaweed.

[0050] As used herein, the term “seed” includes all types of seeds, such as maize, seeds, fruits, tubers, seedlings, and similar forms. The seeds used may be the seeds of the useful plants described above, but may also be the seeds of transgenic plants or plants obtained by conventional breeding methods.

[0051] Throughout this specification and the claims, the terms “comprise,” “comprises,” and “comprising” are used in a non-restrictive sense, synonymous with “including,” “containing,” or “characterized by,” unless the context requires otherwise, and are open-ended, meaning they do not exclude additional, unlisted elements or method steps.

[0052] As used herein, the transitional phrase “essentially consisting of” limits the scope of the claims to certain materials or steps of the subject matter of the claimed disclosure “and which do not substantially affect the essential and novel features.”

[0053] As used herein, the transitional phrase "consisting of" excludes any element, step, or component not specified in the claims.

[0054] As used herein, the term “about” means, when referring to a value, to encompass variations from a particular amount of ±5% in some embodiments, ±2% in some embodiments, ±1% in some embodiments, ±0.5% in some embodiments, and ±0.1% in some embodiments, such variations being appropriate for doing the disclosed method or using the disclosed composition.

[0055] When a range of values ​​is presented, it is understood that, unless explicitly indicated otherwise in the context, it includes all intermediate values ​​up to one-tenth of the lower limit, or any intervening values ​​within the stated range, between the upper and lower limits of that range. The upper and lower limits of any smaller ranges that may independently contain any explicitly excluded limit values ​​are also included. If the stated range includes one or both of the limit values, it also includes the ranges that exclude one or both of those limit values.

[0056] Further definitions are provided below.

[0057] I. Composition The subject matter of this disclosure relates to nitrogen-stabilizing compositions comprising / essentially comprising nitrogen-stabilizing components and organic acid anhydride components. These nitrogen-stabilizing compositions exhibit many beneficial properties, but are not limited to, thermal / chemical / enzymatic stability, increased shelf life, reduced volatility, reduced application rate, ease of preparation, ease of handling, extended / longer-lasting urease and nitrification inhibitory effects, and excellent environmental and toxicological profiles.

[0058] The relative amounts of each component present in the nitrogen-stabilizing composition (i.e., nitrogen stabilizer components and organic acid anhydride components) can vary. For example, in some embodiments, the nitrogen stabilizer components and organic acid anhydride components are present in the nitrogen-stabilizing composition in molar ratios of nitrogen stabilizer components to organic acid anhydride components ranging from about 1:1,000 to about 1,000:1; about 1:100 to about 100:1; about 1:50 to about 50:1; about 1:25 to about 25:1; about 1:10 to about 10:1; about 1:5 to about 5:1; or about 1:2 to 2:1; or about 1:1. In some embodiments, the amount of nitrogen stabilizer components present in the nitrogen stabilization composition is in the range of about 1% to about 99% by weight, about 1% to about 90% by weight, about 1% to about 80% by weight, about 1% to about 70% by weight, or about 1% to about 60% by weight, about 1% to about 50% by weight, about 1% to about 40% by weight, about 1% to about 30% by weight, about 1% to about 20% by weight, or about 1% to about 10% by weight (or about 50% by weight, about 45% by weight, about 40% by weight, about 35% by weight, about 30% by weight, about 25% by weight, about 20% by weight, about 15% by weight or less, or about 10% by weight or less), based on the total weight of the nitrogen stabilization composition.

[0059] In some embodiments, the amount of organic acid anhydride components present in the nitrogen stabilizing composition is in the range of about 1% to about 99% by weight, about 1% to about 90% by weight, about 1% to about 80% by weight, about 1% to about 70% by weight, or about 1% to about 60% by weight, about 1% to about 50% by weight, about 1% to about 40% by weight, about 1% to about 30% by weight, about 1% to about 20% by weight, or about 1% to about 10% by weight (or about 50% by weight, about 45% by weight, about 40% by weight, about 35% by weight, about 30% by weight, about 25% by weight, about 20% by weight, about 15% by weight or less, or about 10% by weight or less), based on the total weight of the nitrogen stabilizer composition.

[0060] In some embodiments, the nitrogen stabilizing composition further comprises one or more nitrification inhibitors and / or one or more urease inhibitors. Such additional nitrification inhibitors and / or urease inhibitors may be the same as or different from the nitrification inhibitors and / or urease inhibitors present in the nitrogen stabilizing component.

[0061] The nitrogen stabilizer components and organic acid anhydride components will be discussed in more detail below.

[0062] A.1. Components of Nitrogen Stabilizers Generally, the nitrogen stabilizer components disclosed may be urease inhibitors and / or nitrification inhibitors. In some embodiments, the urease inhibitors and / or nitrification inhibitors comprise at least one amine-containing moiety. In some embodiments, such amine-containing moieties comprise a primary amine (i.e., -NH2) and / or a secondary amine (i.e., -NHR; where R may be a substituted or unsubstituted alkyl group).

[0063] In some embodiments, the nitrogen stabilizer component is a urease inhibitor. Exemplary urease inhibitors include, but are not limited to, thiophosphate-based urease inhibitors, such as, but are not limited to, N-alkyl-thiophosphate triamides (e.g., N-(n-butyl)thiophosphate triamide (NBPT) and N-(n-propyl)thiophosphate triamide), N-cycloalkyl-thiophosphate triamides, N-aryl-thiophosphate triamides (e.g., N-(2-nitrophenyl)phosphate triamide), and any derivatives thereof. In some embodiments, the urease inhibitor is NBPT.

[0064] In some embodiments, the nitrogen stabilizer component is a combination of urease inhibitors. In some embodiments, one or more urease inhibitors are selected from thiourea-based urease inhibitors, urea-based urease inhibitors, phosphor(di)amide-based urease inhibitors, substituted semicarbazones (e.g., (2E)-2-[(3-fluorophenyl)methylidene]hydrazine-1-carboxamide and (2E)-2-[(4-nitrophenyl)methylidene]hydrazine-1-carboxamide), polyphenols (e.g., methylgalate, baicalin, scutellarin, 1,2,3,4,6-penta-O-galloyl-D-glucoside, caffeic acid, and tannic acid), hydroxyaldehydes (such as salicylaldehyde and vanillin), aminoaromatics (such as methoxyaniline), and combinations thereof.

[0065] In some embodiments, the nitrogen stabilizer component is a nitrification inhibitor. Examples of nitrification inhibitors include, but are not limited to, dicyandiamide (DCD) and any derivative thereof. In some embodiments, the nitrification inhibitor is DCD. In some embodiments, the nitrogen stabilizer component is a combination of nitrification inhibitors. In some embodiments, one or more nitrification inhibitors are selected from pyrazoles (e.g., 3,4-dimethylpyrazole and 4-chloro-3-methylpyrazole), propargylamines, substituted alkynes (e.g., 2-methyl-3-buty-2-ol, 3,5-dimethyl-1-hexyne-3-ol), substituted thioureas (e.g., N-allylthiourea and 1-amidino-2-thiourea), and combinations thereof.

[0066] In some embodiments, the nitrogen stabilizer components are a urease inhibitor and a nitrification inhibitor. For example, in some embodiments, the urease inhibitor is NBPT and the nitrification inhibitor is DCD. The relative amounts of the urease inhibitor and nitrification inhibitor present in the nitrogen stabilizer components can vary. For example, in some embodiments, based on the total weight of the nitrogen stabilizer components, the amount of the urease inhibitor is in the range of about 1 to about 99% by weight, and the amount of the nitrification inhibitor is in the range of about 99 to about 1% by weight. In some embodiments, based on the total weight of the nitrogen-stabilizing composition, the amount of urease inhibitor is in the range of about 10% to about 90% by weight, about 20% to about 80% by weight, about 30% to about 70% by weight, or 40% to about 60% by weight, and the amount of nitrification inhibitor is in the range of about 90% to about 10% by weight, about 80% to about 20% by weight, about 70% to about 30% by weight, or about 60% to about 40% by weight. In some embodiments, based on the total weight of the nitrogen-stabilizing composition, the amount of urease inhibitor is less than about 90% by weight, less than about 80% by weight, less than about 70% by weight, less than about 60% by weight, less than about 50% by weight, less than about 40% by weight, less than about 30% by weight, less than about 20% by weight, or less than about 10% by weight. In some embodiments, based on the total weight of the nitrogen-stabilizing composition, the amount of the nitrification inhibitor is less than about 90% by weight, less than about 80% by weight, less than about 70% by weight, less than about 60% by weight, less than about 50% by weight, less than about 40% by weight, less than about 30% by weight, less than about 20% by weight, or less than about 10% by weight. In some embodiments, the urease inhibitor and the nitrification inhibitor are present in the nitrogen-stabilizing composition in a molar ratio of urease inhibitor to nitrification inhibitor in the range of about 1:100 to about 100:1; about 1:75 to about 75:1, about 1:50 to about 50:1, about 1:25 to about 25:1, about 1:10 to about 10:1, about 1:5 to about 5:1, or about 1:2 to 2:1, or about 1:1.

[0067] A.2.Organic acid anhydride components The disclosed organic acid anhydride components are selected from linear organic acid anhydride monomers, cyclic organic acid anhydride monomers, linear organic acid anhydride polymers, cyclic organic acid anhydride polymers, and combinations thereof, one of which is described in more detail below.

[0068] A.2.1. Linear and cyclic organic acid anhydride monomers The linear organic acid anhydride monomers disclosed herein have the following formula: [ka] In the formula, R1 and R2 are independently selected from substituted or unsubstituted C1-C8 alkyl groups, substituted or unsubstituted C2-C8 alkenyl groups, substituted or unsubstituted C3-C8 cycloalkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups.

[0069] In some embodiments, the linear organic acid anhydride monomer is saturated. In some embodiments, the linear organic acid anhydride is unsaturated. In some embodiments, the linear organic acid anhydride monomer contains 1, 2, 3, 4, 5, or 6 double bonds.

[0070] In some embodiments, the organic acid anhydride monomer is a cyclic organic acid anhydride monomer. In some embodiments, the cyclic organic acid anhydride component is monocyclic. In some embodiments, the cyclic organic acid anhydride is bicyclic or tricyclic.

[0071] In some embodiments, the cyclic organic acid anhydride monomer is monocyclic, as shown in Formula II below: [ka] During the ceremony, [ka] This represents any bond in the above acid anhydride-containing ring structure that may be unsaturated (for example, representing a double bond).

[0072] In some embodiments, the cyclic organic acid anhydride monomer is saturated. In some embodiments, the cyclic organic acid anhydride is unsaturated. In some embodiments, the cyclic organic acid anhydride monomer contains one double bond. In some embodiments, the cyclic organic acid anhydride monomer contains two or more double bonds (e.g., two, three, four, or five double bonds). Examples of cyclic organic acid anhydrides containing one or more double bonds include, but are not limited to, glutaconic acid anhydride, 3,6-dihydro-2,7-oxepindione, 2,7-oxepindione, 4,7-dihydro-2H-oxosin-2,8(3H)-dione, and / or 3,4,7,8-tetrahydro-2,9-oxonidione.

[0073] The ring size of the cyclic organic acid anhydride monomer can vary. For example, in some embodiments, the cyclic organic acid anhydride monomer is selected from 5-membered, 6-membered, 7-membered, 8-membered, 9-membered, 10-membered, 11-membered, or 12-membered cyclic organic acid anhydride monomers, or combinations thereof. Examples of cyclic organic acid anhydride monomers include, but are not limited to, glutaric acid anhydride, adipic acid anhydride, 2,8-oxocanedione, 2,9-oxonanedione, 2,10-oxecanedione, sebaciic acid anhydride, and / or oxacyclododecane-2,12-dione.

[0074] In some embodiments, the cyclic organic acid anhydride monomer is a five-membered cyclic organic acid anhydride monomer. In some embodiments, the cyclic organic acid anhydride monomer is maleic anhydride. In some embodiments, the cyclic organic acid anhydride monomer is succinic anhydride.

[0075] In some embodiments, the cyclic organic acid anhydride monomer is substituted with one or more substituents. In some embodiments, the organic acid anhydride is bicyclic or tricyclic. Examples of bicyclic or tricyclic organic acid anhydride monomers include, but are not limited to, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, hismic anhydride, chloride anhydride, phthalic anhydride, trimellitic anhydride, tetrachlorophthalic anhydride, pyromellitic dianhydride, tetrabromophthalic anhydride, succinic anhydride, citraconic anhydride, maleic anhydride, or combinations thereof.

[0076] A.2.2. Organic acid anhydride polymers As described above, the organic acid anhydride components may also include organic acid anhydride polymers. In some embodiments, the organic acid anhydride polymer is a copolymer of two different repeating units. In some embodiments, the organic acid anhydride polymer is a copolymer of three or more different repeating units. In some embodiments, at least one of the two different repeating units contains an anhydride moiety. In some embodiments, the organic acid anhydride polymer may be, but is not limited to, a random copolymer, an alternating copolymer, a periodic copolymer, a statistical copolymer, or a block copolymer. In some embodiments, the organic acid anhydride polymer is a random copolymer.

[0077] In some embodiments, the organic acid anhydride polymer has a high anhydride content, which makes it highly soluble in water and biodegradable. In some embodiments, the organic acid anhydride polymer has an anhydride content of at least 75 mol%, 80 mol%, 85 mol%, 90 mol%, 95 mol%, or 98 mol%. In some embodiments, the organic acid anhydride polymer has an anhydride content in the range of about 50 mol% to about 99 mol%, about 60 mol% to about 98 mol%, about 70 mol% to about 95 mol%, or about 80 mol% to about 90 mol%.

[0078] The repeating units are derived from the corresponding monomers used in the synthesis of the organic acid anhydride polymer. In some embodiments, the organic acid anhydride polymer contains type B and type C repeating units. These repeating units and their corresponding monomers are discussed in more detail below.

[0079] A.3.1. Type B Repeating Unit The type B repeating unit can be selected from repeating units derived from substituted or unsubstituted monomers of the linear and / or cyclic organic acid anhydrides discussed above, which contain double bonds. In some embodiments, the linear organic acid anhydride may be derived from a monomer of the linear organic acid anhydride according to formula III shown below: [ka] In the formula, R1 is selected from substituted or unsubstituted C1-C8 alkyl groups, substituted or unsubstituted C2-C8 alkenyl groups, substituted or unsubstituted C3-C8 cycloalkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups. n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0080] In some embodiments, the cyclic organic acid anhydride may be derived from a monomer of the cyclic organic acid anhydride represented by formula IV shown below: [ka] In the formula, R1 and R2 are independently selected from -H, -OH, -COOH, -COOR, -OCOH, OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is a substituted or unsubstituted alkyl group. In the above ring, n represents the number of carbon atoms as an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. In the above ring, m represents the number of carbon atoms as an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0081] The ring size of the cyclic organic acid anhydride moiety in Formula IV above can vary. For example, in some embodiments, the cyclic organic acid anhydride moiety is selected from 5-membered, 6-membered, 7-membered, 8-membered, 9-membered, 10-membered, 11-membered, or 12-membered cyclic organic acid anhydride monomers, or combinations thereof. In some embodiments, the cyclic organic acid anhydride monomer is a 5-membered cyclic organic acid anhydride moiety.

[0082] In some embodiments, the type B repeating unit is derived from maleic anhydride. In some embodiments, the type B repeating unit is derived from itaconic anhydride.

[0083] In some embodiments, the unsubstituted or substituted alkyl group is a C1-C8 alkyl group.

[0084] A.3.2. Type C Repeating Unit The C-type repeating unit can be selected from repeating units derived from substituted or unsubstituted monomers of alkenes according to formula V: [ka] In the formula, R1, R2, R3, and R4 are independently selected from -H, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is a substituted or unsubstituted alkyl group.

[0085] Examples of classes of monomers that can be used include alkenes, e.g., ethylene, propylene, butene-l (butylene), isobutylene, pentene-l, hexene-l, heptene-l, octene-l, 2,4,4-trimethylpentene-l, trimethylethylene, trans-stilbene and methylenecyclohexane; cycloalkenes, e.g., cyclopentene and cyclohexene; aralkenes, e.g., styrene, trimethylstyrene, α-ethylstyrene and other substituted derivatives of styrene; vinyl ethers, e.g., methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, isopropyl vinyl ether and isobutyl vinyl ether; isopropenyl ethers, e.g., methyl isopropenyl ether; ethylenically unsaturated carboxylic acids, their esters and Nitriles, such as methyl acrylate, ethyl acrylate, 2-ethylhexyl acrylate, acrylonitrile, methyl methacrylate, and methacrylonitrile; ethylenically unsaturated dicarboxylic acids, their mono- and diesters, nitriles, anhydrides, and imides, such as dimethyl maleate, diethyl maleate, dibutyl maleate, maleic anhydride, maleimide, N-methylmaleimide, N-ethylmaleimide, N-phenylmaleimide, Np-chlorophenylmaleimide, dimethyl fumarate, diethyl fumarate, dibutyl fumarate, itaconic anhydride, monobutyl itaconic anhydride, citraconic anhydride, mesaconic anhydride, and vinylidene cyanide; and halogen-substituted alkenes, such as vinyl chloride, vinylidene chloride, allyl chloride, and methyl chloride.

[0086] In some embodiments, the C-type repeating unit is derived from ethylene, propylene, butylene, isobutylene, styrene, methyl vinyl ether, or a combination thereof.

[0087] In some embodiments, the substituted or unsubstituted alkyl group is a substituted or unsubstituted C1-C8 alkyl group.

[0088] In a broad sense, the organic acid anhydride polymers disclosed herein include repeating polymer subunits composed of two different parts, obtained from a group consisting of those individually and respectively named B and C parts for ease of reference, and alternatingly, cyclic organic acid anhydride polymers may be formed from repeating B parts. Thus, exemplary polymer subunits may be BC, CB, BB, or any other combination of B and C parts, and furthermore, in a given cyclic organic acid anhydride polymer, different polymer subunits may include different types of parts, for example, in a BC repeating polymer unit polymer, the B parts may differ in different units.

[0089] In detail, part B is general formula VI: [ka] The formula is as follows: R1 and R4 are independently selected from -H, -OH, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl; R is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; and R2 and R3 are independently selected from bonded or substituted or unsubstituted C1-C8.

[0090] Part C is given by general formula VII: [ka] This can be further classified into the following three sub-formulas: [ka] In the formula, R1R2, R3, and R4 are independently selected from -H, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0091] As can be understood, the disclosed organic acid anhydride polymers may have repeat polymer subunits in different sequences as defined above (for example, a polymer containing B and C subunits may contain all two forms of the B subunit and all four forms of the C subunit). However, for reasons of cost and ease of synthesis, the most useful polymers are those containing repeat polymer subunits composed of B and C portions.

[0092] In some embodiments, the organic acid anhydride polymer consists of repeat polymer subunits formed from B and C portions and has a generalized formula VIII: [ka] In the formula, R1R2, R3, and R4 are independently selected from -H, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. n is an integer greater than 2.

[0093] In some embodiments, other forms of this polymer can have a wide range of repeating unit concentrations in the polymer. For example, polymers having various ratios of B:C (e.g., 10:90, 60:40, 50:50, and even 0:100) are contemplated and encompassed by the subject matter of this disclosure. Such polymers are produced by varying amounts of monomers in the reaction mixture from which the final product is ultimately formed, and the B and C repeating units may be arranged in a random order or in an alternating pattern within the polymer backbone.

[0094] In some embodiments, at least about 80 mol%, about 85%, about 90%, or about 95% of the repeating units are type B repeating units. In some embodiments, these repeating units are randomly located along the polymer.

[0095] The polymers of the subject matter of this disclosure may have a wide variety of molecular weights, mainly depending on the desired end application, for example, in the range of about 500 to about 5,000,000 Da, about 1,000 to about 500,000 Da, or about 10,000 to about 50,000 Da. Furthermore, n may be in the range of about 1 to 10,000, more preferably about 1 to 5,000.

[0096] Generally, the above polymers can be produced by free radical polymerization, thereby converting selected monomers into polymers having repeating units. Such polymers can be further modified to impart specific structures and / or properties. Free radicals can be generated using a variety of techniques, such as the addition of peroxides, hydroperoxides, azo initiators, persulfates, percarbonates, peracids, charge transfer complexes, radiation (e.g., UV, electron beams, X-rays, gamma rays, and other types of ionizing radiation), and combinations of these techniques. A wide range of methods and techniques for initiating free radical polymerization are well known in the field of polymer chemistry.

[0097] Polymerization reactions are carried out using the desired monomer concentration in a suitable solvent system, i.e., a system that does not excessively hinder the desired polymerization. Many suitable aqueous or non-aqueous solvent systems can be used, such as ketones, alcohols, esters, ethers, aromatic solvents, water, and mixtures thereof. Water alone, as well as lower (C1-C4) ketones and alcohols, are particularly preferred and, if desired, can be mixed with water. In some examples, polymerization reactions are carried out under an inert gas, mostly nitrogen or argon, with oxygen substantially excluded. There is no particular importance in the type of apparatus used for polymer synthesis; that is, stirred-tank reactors, continuous stirred-tank reactors, plug-flow reactors, tube reactors, and any combination of the aforementioned arranged in series can be used. A wide range of suitable reaction configurations are well known in the art of polymerization.

[0098] Generally, the initial polymerization step is carried out at a temperature of approximately 0°C to 120°C (or at approximately 30°C to 95°C for approximately 0.25 hours to 24 hours or approximately 0.25 hours to 5 hours). Typically, the reaction is carried out by continuous stirring, and once the polymerization reaction is complete, the polymer can be isolated.

[0099] B. Preparation method Methods for preparing nitrogen-stabilized compositions disclosed herein generally involve contacting nitrogen stabilizer components with cyclic organic acid anhydride components. In this context, the term “contact” means that the nitrogen stabilizer is exposed to, contacted with, and / or physically mixed with the cyclic organic acid anhydride components. Contact between the two components typically occurs when both components are present in the same space (e.g., a reaction vessel and / or container) without being physically separated.

[0100] The amounts of nitrogen stabilizer components and acid anhydride components may vary. In some embodiments, the amounts of nitrogen stabilizer and cyclic organic acid anhydride present in the contact step of the above method are in molar ratios of nitrogen stabilizer to cyclic organic acid anhydride components in the range of about 1:10 to about 10:1, about 1:8 to about 8:1, about 1:5 to about 5:1, about 1:3 to about 3:1, about 1:2 to about 2:1, or about 1:1.

[0101] In some embodiments, the contact step in the above method may be carried out without a solvent. In some embodiments, the contact step may be carried out in a solvent. Exemplary solvents include, but are not limited to, alcohols (e.g., methanol, ethanol, isopropanol), ethers (e.g., diethyl ether, tetrahydrofuran), halogenated solvents (e.g., dichloromethane), esters (e.g., ethyl acetate), aromatic compounds (e.g., benzene, toluene), and nonpolar solvents (e.g., acetonitrile, dimethyl sulfoxide).

[0102] In some embodiments, the above contact step may be carried out at room temperature (e.g., about 25°C). In some embodiments, the above contact step may be carried out at a high temperature (e.g., at least about 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or at least about 100°C). In some embodiments, the above contact step may be carried out at a temperature below room temperature (e.g., below about 20, 10, 5, 0, -5, -10, -15, below -20°C, or below about -30°C). In some embodiments, the above contact step may be carried out at a temperature in the range of about 30°C to about 100°C, about 40°C to about 80°C, about 45°C to about 75°C, or about 50°C to about 70°C. In some embodiments, the above contact step may be carried out at a temperature below room temperature (e.g., below about 20, 10, 5, 0, -5, -10, -15, below -20°C, or below about -30°C). In some embodiments, the above contact step may be carried out at a temperature in the range of about -30°C to about 10°C, about -25°C to about 5°C, about -15°C to about 0°C, or about -10°C to about -5°C.

[0103] Once the contact step is complete, any residual liquid (e.g., solvent and / or excess nitrogen stabilizer / cyclic organic acid anhydride components) may be removed according to methods known in the art, and the remaining crude material may be purified, if necessary, using purification methods known in the art (e.g., high-pressure liquid chromatography (HPLC), gas chromatography (GC), distillation, crystallization, chromatographic purification (i.e., silica, alumina), etc.).

[0104] C. Nitrogen-stabilized compositions As described above, nitrogen-stabilized compositions can exhibit desirable properties such as increased thermal / chemical / enzymatic stability, increased shelf life, reduced volatility, reduced application rate, improved viscosity, ease of preparation, ease of handling, extended / longer-lasting urease and nitrification inhibitory effects, and excellent environmental and toxicity profiles, all of which generally contribute to improved performance in the field.

[0105] In some embodiments, the nitrogen stabilization composition further comprises a second nitrification inhibitor and / or urease inhibitor. The amount of the second nitrification inhibitor and / or urease inhibitor may vary. In some embodiments, the amount of the second nitrification inhibitor and / or urease inhibitor is in the range of about 1% to about 99% by weight, about 5% to about 90% by weight, about 10% to about 80% by weight, about 10% to about 70% by weight, about 20% to about 60% by weight, or about 30% to about 50% by weight, based on the total weight of the nitrogen stabilization composition. In some embodiments, the second nitrification inhibitor and / or urease inhibitor is the same as the nitrification inhibitor and / or urease inhibitor present in the nitrogen stabilizer component. In some embodiments, the second nitrification inhibitor and / or urease inhibitor is different from the nitrification inhibitor and / or urease inhibitor present in the nitrogen stabilizer component. In some embodiments, the second nitrification inhibitor is nitrapyrine.

[0106] In some embodiments, the amounts of nitrogen stabilizer components and the second nitrification inhibitor and / or urease inhibitor present in the nitrogen stabilization composition may be in the weight ratio of nitrogen stabilizer components to the second nitrification inhibitor and / or urease inhibitor in the range of about 1:100 to about 100:1, about 1:80 to about 80:1, about 1:50 to about 50:1, about 1:30 to about 30:1, about 1:20 to about 20:1, about 1:10 to about 10:1, about 1:8 to about 8:1, about 1:5 to about 5:1, about 1:3 to about 3:1, about 1:2 to about 2:1, or about 1:1.

[0107] In some embodiments, the nitrogen-stabilized compositions disclosed herein are chemically / thermally / and / or enzymatically more stable than compositions containing nitrogen stabilizers that do not contain organic acid anhydrides. In some embodiments, the nitrogen-stabilized compositions are chemically at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% more stable than compositions containing nitrogen stabilizers that do not contain organic acid anhydrides. In some embodiments, the nitrogen-stabilized compositions are thermally at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% more stable than compositions containing nitrogen stabilizers that do not contain organic acid anhydrides. In some embodiments, nitrogen-stabilized compositions are at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% more enzymatically stable than compositions containing nitrogen stabilizers that do not contain organic acid anhydride components. The thermal / chemical / enzymatic stability of the disclosed compositions is measured as a function of the amount of nitrogen stabilizer present after a certain period of time when exposed to chemical / thermal / enzymatic stimuli.

[0108] In some embodiments, the nitrogen-stabilized compositions disclosed herein have lower volatility compared to compositions containing nitrogen stabilizers that do not contain cyclic organic acid anhydride components. In some embodiments, the nitrogen-stabilized compositions have at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% lower volatility compared to compositions containing nitrogen stabilizers that do not contain cyclic organic acid anhydride components.

[0109] In some embodiments, the nitrogen-stabilizing compositions disclosed herein inhibit the decomposition of urea. In some embodiments, the nitrogen-stabilizing compositions inhibit the decomposition of urea by at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95%.

[0110] In some embodiments, the nitrogen stabilizing composition provides a stable and continuous release of nitrogen stabilizer components. The amount of nitrogen stabilizer components released over a given period may vary. Those skilled in the art will recognize methods for adjusting the release of nitrogen stabilizer components accordingly. For example, those skilled in the art will recognize methods for adjusting the release characteristics of a particular nitrogen stabilizer by selecting appropriate organic acid anhydride components to achieve a desired release rate of the nitrogen stabilizer over a particular period.

[0111] In some embodiments, nitrogen stabilizer components are released from the nitrogen stabilization composition at stable concentrations ranging from about 1 to about 100 mg / g, about 1 to about 75 mg / g, about 1 to about 50 mg / g, about 1 to about 40 mg / g, about 1 to about 30 mg / g, about 1 to about 20 mg / g, about 1 to about 10 mg / g, or about 1 to about 5 mg / g.

[0112] In some embodiments, nitrogen stabilizer components are released from the nitrogen stabilization composition over periods of 1 to 4 weeks, 1 to 3 weeks, or 1 to 2 weeks. In some embodiments, nitrogen stabilizer components are released from the nitrogen stabilization composition over periods of 1 to 30 days, 1 to 20 days, 1 to 10 days, or over periods of at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, or 31 days. In some embodiments, nitrogen stabilizer components are released from the nitrogen stabilization composition over periods of approximately 1 to 6 months, 1 to 5 months, 1 to 4 months, 1 to 3 months, or approximately 1 to 2 months.

[0113] In some embodiments, nitrogen stabilizer components are released from the nitrogen stabilization composition at concentrations ranging from about 1 to about 20 mg / g over a period of at least 10 days.

[0114] II. Formulations Generally, nitrogen stabilizer compositions can be used neat (solvent-free) or can be solvated with a vehicle such as an organic solvent and / or formulated with other components for forming a useful formulation. In some embodiments, the described nitrogen stabilizer compositions contain relatively little or no water. Therefore, in some embodiments, the amount of water present neat in the nitrogen stabilizer composition is about 10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about 3%, about 2%, or less than about 1%, or less than 0.5% w / w, based on the total weight of the nitrogen stabilizer composition.

[0115] A. Vehicle In some embodiments, the vehicle for solvating the neat nitrogen stabilizer composition comprises one or more organic solvents. For example, in some embodiments, the vehicle essentially comprises / consists of / an organic solvent selected from glycol solvents, lactone solvents, aprotic solvents, alcohol solvents, amine stabilizers, and combinations thereof. In some embodiments, the vehicle essentially comprises / consists of / an organic solvent selected from lactone solvents, bipolar aprotic solvents, amine stabilizers, and combinations thereof. For example, in some embodiments, the vehicle essentially comprises / consists of / an organic solvent selected from 4-butyl-γ-butyrolactone, N-methyl-2-pyrrolidone, dimethyl sulfoxide (DMSO), monoethanolamine, and combinations thereof. In some embodiments, the vehicle essentially comprises / consists of / an organic solvent selected from aprotic solvents, amine stabilizers, and combinations thereof. In some embodiments, the vehicle is DMSO and monoethanolamine.

[0116] In some embodiments, the vehicle contains / consists of / essentially consists of an aprotic solvent. Suitable aprotic solvents include, for example, dichloromethane, dimethylacetamide, dimethylformamide, dimethyl sulfoxide (DMSO), ethyl acetate, acetone, acetonitrile, hexamethylphosphoramide, dimethyl sulfone, sulfolane, 1,3-dimethyl-2-imidazoidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, methyl acetate, ethyl lactate, N-methylpyrrolidone, tetrahydrofuran, and propylene carbonate. In some embodiments, the aprotic solvent is DMSO.

[0117] In some embodiments, the vehicle comprises / consists of / essentially comprises an amine stabilizer. Exemplary amine stabilizers include, but are not limited to, 1,2-diaminocyclohexane (DCH), bis(hexamethylene)triamine (BHT), monomethanolamine, monoethanolamine, ethylaminoethanol, dimethylaminoethanol, isopropylaminoethanol, diethanolamine, triethanolamine, methylaminoethanol, aminopropanol, methylaminopropanol, dimethylaminopropanol, aminobutanol, dimethylaminobutanol, aminobutanediol, trihydroxymethylaminoethane, diethylaminopropanediol, 1-aminocyclopentanemethanol, and aminobenzyl alcohol, or heterocycles comprising at least one nitrogen atom as a ring member and / or substituted with an amine group on at least one carbon atom, and substituted with a hydroxyalkyl group or hydroxyl group, such as methylaminomethyl-1,3-dioxolane, on at least one other carbon. In some embodiments, the amine stabilizer is monomethanolamine.

[0118] In some embodiments, the vehicle comprises / consists of / essentially comprises a glycol-based solvent. Examples of glycols and glycol-based solvents include, but are not limited to, aliphatic dihydroxy(dihydric) alcohols. In one embodiment, examples of glycol-based solvents include, but are not limited to, polypropylene glycol, triethylene glycol, glycol alkyl ethers, such as dipropylene glycol methyl ether and diethylene glycol. In another embodiment, examples of glycol-based solvents, but are not limited to, polyglycols, such as polyethylene glycol (PEG) and polypropylene glycol. Glycols are generally defined by the formula C n H 2nIt is represented by (OH)2, where n is at least 2. Non-limiting examples of glycols include ethylene glycol (glycol), propylene glycol (1,2-propanediol), 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,9-nonanediol, 1,10-decanediol, 1,8-octanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, and 2,4-pentanediol. Examples include 2,5-hexanediol, 4,5-octanediol and 3,4-hexanediol, neopentyl glycol, pinacol, 2,2-diethyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, 2-ethyl-2-butyl-1,3-propanediol, isobutylene glycol, 2,3-dimethyl-1,3-propanediol, 1,3-diphenyl-1,3-propanediol, and 3-methyl-1,3-butanediol. Polyglycol-based solvents are not limited to, but include polyethylene glycol (PEG) 200-6000 mono and dilaurates, for example PEG600 dilaurate, PEG600 monolaurate, PEG1000 dilaurate, PEG1000 monolaurate, PEG1540 dilaurate and PEG1540 monolaurate, polyethylene glycol 200-6000 mono and dioleate, for example PEG400 monooleate, PEG600 dioleate, PEG600 monooleate, P Examples include EG1000 monooleate, PEG1540 dioleate, PEG1540 monooleate, and polyethylene glycol 200-6000 mono and distearates, such as PEG400 distearate, PEG400 monostearate, PEG600 distearate, PEG600 monostearate, PEG1000 distearate, PEG1000 monostearate, PEG1540 distearate, PEG1540 monostearate, and PEG3000 monostearate.

[0119] In some embodiments, the vehicle comprises / consists of / essentially comprises a lactone-based solvent. Lactones are cyclic carboxylic acid esters of various ring sizes. In some embodiments, the lactone-based solvent is selected from α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone. In some embodiments, α-acetolactone, β-propiolactone, γ-butyrolactone, and / or δ-valerolactone are optionally substituted with, for example, alkyl groups or halogens. Exemplary lactone-based solvents include, but are not limited to, 4-butyl-γ-butyrolactone, mucobromic acid, mucohydrochloric acid, β-butyrolactone, γ-butyrolactone, 3-hydroxy-γ-butyrolactone, α-methylene-γ-butyrolactone, and γ-valerolactone.

[0120] In some embodiments, the vehicle comprises / consists of / essentially comprises an alcohol solvent. The alcohol solvent is any organic solvent containing a hydroxyl group (-OH). Exemplary alcohol solvents include, but are not limited to, ethanol, methanol, ter-amyl alcohol, 2-methyl-1-butanol, 2-ketyl-1-pentanol, 3-methyl-2-butanol, furfuryl alcohol, 2-butanol, N-butanol, isobutanol, isopropyl alcohol, 2-pentanol, 1-propanol, and combinations thereof.

[0121] In some embodiments, the vehicle contains relatively little water. In some embodiments, the vehicle (e.g., an organic solvent) contains water at a rate of about 10% w / w, about 9% w / w, about 8% w / w, about 7% w / w, about 6% w / w, about 5% w / w, about 4% w / w, about 3% w / w, about 2% w / w, about 1% w / w, about 0.9% w / w, about 0.8% w / w, about 0.7% w / w, about 0.6% w / w, about 0.5% w / w, about 0.4% w / w, about 0.3% w / w, or less than about 0.1% w / w, based on the total weight of the vehicle.

[0122] B. Formulations The vehicles disclosed herein, but not limited to, may be used in formulations containing the above-mentioned nitrogen-stabilizing compositions and / or their components to provide formulations exhibiting many beneficial properties, such as thermal and / or chemical stability, increased shelf life of formulations, reduced volatility of formulations, reduced application rate, improved viscosity of formulations, absence of any strong or undesirable odors or smells, ease of preparation of formulations, ease of handling of formulations, extended / longer-lasting effects of urease and nitrification inhibition, and excellent environmental and toxicological profiles.

[0123] In some embodiments, the formulation comprises the disclosed nitrogen-stabilizing composition and the vehicle described above. The amount of nitrogen-stabilizing composition present in the formulation may vary. For example, in some embodiments, the amount of nitrogen-stabilizing composition present in the formulation is in the range of about 5% to about 50% w / w, about 10% to about 45% w / w, about 15% to about 40% w / w, about 20% to about 35% w / w, or about 25% to about 30% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrogen-stabilizing composition present in the formulation is in the range of about 1% to about 75% w / w, about 10% to about 65% w / w, about 20% to about 65% w / w, about 30% to about 65% w / w, or about 40% to about 65% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrogen-stabilizing composition present in the formulation is in the range of about 1% to about 40% w / w, about 10% to about 35% w / w, about 15% to about 35% w / w, about 20% to about 35% w / w, about 25% to about 35% w / w, about 27% to about 35% w / w, or about 30% to about 35% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrogen-stabilizing composition present in the formulation is in the range of about 15% to about 30% w / w, about 15% to about 28% w / w, about 15% to about 25% w / w, or about 15% to about 23% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrogen-stabilizing composition present in the formulation is in the range of about 25% to about 40% w / w, about 25% to about 35% w / w, about 22% to about 28% w / w, or about 22% to about 33% w / w, based on the total weight of the formulation.

[0124] In some embodiments, the amount of nitrogen stabilizer components (which are part of the nitrogen stabilization composition) can vary. In some embodiments, the amount of nitrogen stabilizer components present in the formulation is in the range of about 1% to about 50% w / w, about 5% to about 50% w / w, about 5% to about 40% w / w, about 10% to about 40% w / w, about 10% to about 30% w / w, or about 10% to about 25% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrogen stabilizer components present in the formulation is in the range of about 5% to about 30%, about 5% to about 25%, about 5% to about 20%, about 5% to about 15%, or about 5% to about 10%. In some embodiments, the amount of nitrogen stabilizer components present in the formulation is in the range of about 15% to about 30%, about 15% to about 25%, or about 15% to about 20%. In some embodiments, the nitrogen stabilizer component is a urease inhibitor. In some embodiments, the nitrogen stabilizer component is a nitrification inhibitor. In some embodiments, the nitrogen stabilizer component is a urease inhibitor and a nitrification inhibitor.

[0125] In some embodiments, the nitrogen stabilizer component includes a urease inhibitor. The amount of urease inhibitor (which is part of the nitrogen stabilizer component) present in the formulation may vary. For example, in some embodiments, the amount of urease inhibitor present in the formulation is in the range of about 5% to about 50% w / w, 5% to about 25% w / w, 5% to about 20% w / w, or 5% to about 15% w / w, based on the total weight of the formulation. In some embodiments, the amount of urease inhibitor present in the formulation is in the range of about 5% to about 30% w / w, about 5% to about 25% w / w, about 5% to about 20% w / w, about 5% to about 15% w / w, about 5% to about 10% w / w, or about 5% to about 8.5% w / w, based on the total weight of the formulation. In some embodiments, the amount of urease inhibitor present in the formulation is in the range of about 15% to about 25%, about 15% to about 20%, or about 10% to about 20%, about 10% to about 15%, about 12.5% ​​to about 15%, or about 7.5% to about 20%, about 8.5% to about 20%, about 8.5% to about 15%, or about 8.5% to about 12.5%. In some embodiments, the urease inhibitor is NBPT.

[0126] In some embodiments, the nitrogen stabilizer component includes a nitrification inhibitor. The amount of nitrification inhibitor present in the formulation may vary. For example, in some embodiments, the amount of nitrification inhibitor present in the formulation is in the range of about 1% to about 30%, about 5% to about 25%, about 5% to about 20%, 5% to about 10%, or 10% to about 20% w / w, based on the total weight of the formulation. In some embodiments, the amount of nitrification inhibitor present in the formulation is in the range of about 5% to about 30% w / w, about 5% to about 25% w / w, about 5% to about 20% w / w, about 5% to about 15% w / w, about 5% to about 10% w / w, or about 5% to about 7.5% w / w, based on the total weight of the formulation. In some embodiments, the amount of urease inhibitor present in the formulation is in the range of about 15% to about 25%, about 15% to about 20%, or about 10% to about 25%, about 10% to about 20%, about 10% to about 15%, or about 7.5% to about 25%, or about 7.5% to about 15%. In some embodiments, the nitrification inhibitor is DCD.

[0127] In some embodiments, the amount of organic acid anhydride components (which are part of the nitrogen-stabilizing composition) present in the formulation is in the range of about 1% to about 20% w / w, about 1% to about 15% w / w, or about 1% to about 10% w / w, based on the total weight of the formulation. In some embodiments, the amount of organic acid anhydride components present in the formulation is in the range of about 5% to about 15%, about 5% to about 10%, or about 5% to about 8%. In some embodiments, the organic acid anhydride components are polymers disclosed herein.

[0128] In some embodiments, the vehicle can be used to solvate and / or formulate one or more components of the nitrogen-stabilizing composition. For example, in some embodiments, the formulation comprises the nitrogen-stabilizing composition and the vehicle disclosed herein. In some embodiments, the formulation comprises the urease inhibitor and the vehicle disclosed herein. In some embodiments, the urease inhibitor is NBPT.

[0129] In some embodiments, the formulation comprises a nitrification inhibitor and a vehicle as disclosed herein. In some embodiments, the nitrification inhibitor is DCD.

[0130] In some embodiments, the formulation comprises a nitrification inhibitor, a urease inhibitor, and a vehicle as disclosed herein. In some embodiments, the nitrification inhibitor is DCD, and the urease inhibitor is NBPT.

[0131] In some embodiments, the formulation comprises an organic acid anhydride component and a vehicle as disclosed herein. In some embodiments, the organic acid anhydride component is a polymer as disclosed herein.

[0132] The vehicle for solvating and / or formulating the above-described compositions and / or components comprises an aprotic solvent and an amine stabilizer. Those skilled in the art will recognize that the amounts of aprotic solvent and amine stabilizer present in the formulation can vary. For example, in some embodiments, the amount of aprotic solvent is in the range of about 1% to about 80% w / w, about 10% to about 80% w / w, about 20% to about 80% w / w, about 40% to about 80% w / w, 50% to about 75% w / w, about 55% to about 75% w / w, or about 60% to about 75% w / w, based on the total weight of the formulation. In some embodiments, the amount of aprotic solvent present in the formulation is in the range of about 10% to about 75% w / w, about 10% to about 60% w / w, about 10% to about 50% w / w, about 10% to about 45% w / w, or about 20% to about 45% w / w, based on the total weight of the formulation.

[0133] In some embodiments, the amount of aprotic solvent is about 80% w / w, about 75% w / w, about 70% w / w, about 65% w / w, about 60% w / w, about 55% w / w, about 50% w / w, about 45% w / w, about 40% w / w, about 30% w / w, or less than about 20% w / w, based on the total weight of the formulation. In some embodiments, the amount of aprotic solvent is about 5% w / w, about 10% w / w, about 15% w / w, about 20% w / w, about 25% w / w, about 30% w / w, about 35% w / w, about 40% w / w, about 45% w / w, about 50% w / w, about 55% w / w, about 60% w / w, about 65% w / w, about 70% w / w, or more than about 75% w / w, based on the total weight of the formulation. In some embodiments, the aprotic solvent is DMSO. In some embodiments, the amount of amine stabilizer is in the range of about 1% to about 15% w / w, about 5% to about 10% w / w, about 3% to about 8% w / w, or about 8% to about 12% w / w, based on the total weight of the formulation. In some embodiments, the amount of amine stabilizer is about 15% w / w, about 14% w / w, about 13% w / w, about 12% w / w, about 11% w / w, about 10% w / w, about 9% w / w, about 8% w / w, about 7% w / w, about 6% w / w, about 5% w / w, about 4% w / w, about 3% w / w, about 2% w / w, or less than about 1% w / w, based on the total weight of the formulation. In some embodiments, the amount of amine stabilizer is about 1% w / w, about 2% w / w, about 3% w / w, about 4% w / w, about 5% w / w, about 6% w / w, about 7% w / w, about 8% w / w, about 9% w / w, about 10% w / w, or more than about 12% w / w, based on the total weight of the formulation. In some embodiments, the amine stabilizer is a monomethanolamine.

[0134] Therefore, in some embodiments, the formulations disclosed herein include a nitrogen stabilizer composition, an aprotic solvent, and an amine stabilizer.

[0135] In some embodiments, the formulations disclosed herein include a nitrogen stabilizer component, an aprotic solvent, and an amine stabilizer.

[0136] In another embodiment, the formulation disclosed herein comprises an organic acid anhydride component, an aprotic solvent, and an amine stabilizer.

[0137] A formulation comprising a nitrogen stabilizer component and an organic acid anhydride component, similar to any of the embodiments described above.

[0138] A formulation wherein the nitrogen stabilizer component is a urease inhibitor and / or nitrification inhibitor, similar to any of the embodiments described above.

[0139] In some embodiments, the formulations disclosed herein include a nitrogen-stabilizing composition comprising a nitrogen-stabilizing component and an organic acid anhydride component, wherein the nitrogen-stabilizing component is a urease inhibitor and / or nitrification inhibitor; an aprotic solvent; and an amine stabilizer.

[0140] A formulation wherein the nitrogen stabilizer component is N-(n-butyl)thiophosphate triamide (NBPT) and / or dicyanamide (DCD), similar to any of the embodiments described above.

[0141] A formulation in which the organic acid anhydride component is an organic acid anhydride polymer, similar to any of the embodiments described above.

[0142] A formulation in which the organic acid anhydride polymer is a copolymer containing at least two different repeating units, each containing one type B repeating unit and one type C repeating unit.

[0143] A formulation in which the copolymer is a random copolymer, as in any of the embodiments described above.

[0144] A formulation in which the type B repeating unit is derived from a (un)substituted monomer of maleic anhydride, a (un)substituted monomer of itaconic anhydride, or a combination thereof, as in any of the embodiments described above.

[0145] A formulation, similar to any of the embodiments described above, wherein the type B repeating unit is derived from an (un)substituted monomer of maleic anhydride.

[0146] A formulation in which, as in any of the embodiments described above, at least about 50 mol% of the repeating units of the organic acid anhydride polymer are type B repeating units.

[0147] A formulation wherein the organic acid anhydride polymer contains C-type repeating units derived from (un)substituted alkenes, similar to any of the embodiments described above.

[0148] A formulation in which the alkene is selected from ethylene, propylene, butylene, isobutylene, styrene, methyl vinyl ether, and combinations thereof, as in any of the embodiments described above.

[0149] Similar to any of the embodiments described above, the organic acid anhydride polymer has a structure according to the following formula: [ka] In the formula, R1, R2, R3, and R4 are independently selected from -H, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is an (un)substituted C1-C8 alkyl group, an (un)substituted C2-C8 alkenyl group, an (un)substituted aryl group, or an (un)substituted heteroaryl group. n is an integer greater than 2, in the formulation.

[0150] A formulation in which the aprotic solvent is selected from dichloromethane, dimethylacetamide, dimethylformamide, dimethyl sulfoxide (DMSO), ethyl acetate, acetone, acetonitrile, hexamethylphosphoramide, dimethyl sulfone, sulfolane, 1,3-dimethyl-2-imidazoidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, methyl acetate, ethyl lactate, N-methylpyrrolidone, tetrahydrofuran, and propylene carbonate, as in any of the embodiments described above.

[0151] A formulation in which the aprotic solvent is dimethyl sulfoxide (DMSO), similar to any of the embodiments described above.

[0152] A formulation in which the amine stabilizer is selected from 1,2-diaminocyclohexane (DCH), bis(hexamethylene)triamine (BHT), monoethanolamine, ethylaminoethanol, dimethylaminoethanol, isopropylaminoethanol, diethanolamine, triethanolamine, methylaminoethanol, aminopropanol, methylaminopropanol, dimethylaminopropanol, aminobutanol, dimethylaminobutanol, aminobutanediol, trihydroxymethylaminoethane, diethylaminopropanediol, 1-amino-cyclopentanemethanol, and aminobenzyl alcohol, as in any of the embodiments described above.

[0153] A formulation in which the amine stabilizer is monoethanolamine, similar to any of the embodiments described above.

[0154] A formulation comprising DCD, NBPT, and a polymer disclosed herein formulated in DMSO and monomethanolamine, similar to any of the embodiments described above.

[0155] A formulation in which the nitrogen-stabilizing composition is present in an amount of about 5% to about 50% w / w based on the total weight of the stabilizing formulation, as in any of the embodiments described above.

[0156] A formulation in which the aprotic solvent is present in an amount of about 50% to about 75% w / w based on the total weight of the stabilized formulation, as in any of the embodiments described above.

[0157] A formulation in which the amine stabilizer is present in an amount of about 3% to about 8% w / w based on the total weight of the stabilized formulation, as in any of the embodiments described above.

[0158] A formulation in which the nitrogen stabilizer component is present in an amount of about 5% to about 50% w / w based on the total weight of the stabilized formulation, as in any of the embodiments described above.

[0159] A formulation comprising, as in any of the embodiments described above, a nitrogen stabilizer component comprising a urease inhibitor present in an amount of about 5% to about 20% w / w based on the total weight of the stabilized formulation, and a nitrification inhibitor present in an amount of about 5% to about 20% w / w based on the total weight of the stabilized formulation.

[0160] As in any of the embodiments described above, the nitrogen stabilizer component comprises a vehicle containing a urease inhibitor present in an amount of about 5% to about 20% w / w, a nitrification inhibitor present in an amount of about 5% to about 20% w / w, a polymer disclosed herein present in an amount of about 1% to about 10%, an aprotic solvent present in an amount of about 45% to about 75%, and an amine stabilizer present in an amount of about 3% to about 8% w / w, all weights being based on the total weight of the stabilized formulation. In some embodiments, the formulations disclosed herein are more chemically and / or thermally stable than formulations containing a nitrogen stabilization composition that does not contain an organic acid anhydride component. In some embodiments, the formulations are at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% more chemically stable than formulations containing a nitrogen stabilization composition that does not contain an organic acid anhydride component. In some embodiments, the formulations are at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% more thermally stable than formulations containing nitrogen-stabilizing compositions that do not contain organic acid anhydride components. The thermal / chemical / enzymatic stability of the disclosed compositions is measured as a function of the amount of nitrogen-stabilizing components present after a certain period of time when exposed to chemical and / or thermal and / or enzymatic stimuli.

[0161] In some embodiments, the formulations disclosed herein have lower volatility compared to formulations containing a nitrogen-stabilizing composition that does not contain organic acid anhydride components. In some embodiments, the formulations have at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or at least 95% lower volatility compared to formulations containing a nitrogen-stabilizing composition that does not contain organic acid anhydride components.

[0162] In some embodiments, the formulations disclosed herein exhibit improved viscosity compared to formulations containing nitrogen-stabilized compositions that do not contain organic acid anhydride components. In some embodiments, the viscosity of the disclosed formulations ranges from about 50 to about 1,740 cps when measured at room temperature (25.5°C). In some embodiments, the viscosity of the disclosed formulations ranges from about 200 to about 9,500 cps when measured at about 2°C.

[0163] In some embodiments, the formulations disclosed herein do not contain strong, undesirable odors and / or odors. Undesirable odors or odors may be characterized by having a sulfur-containing odor or odor. Surprisingly, the formulations disclosed herein, despite their DMSO content, do not exhibit any undesirable odors and / or odors. The absence of undesirable odors and / or odors makes the formulations more user-friendly compared to other formulations that may exhibit undesirable odors and / or odors. Detection and / or identification of any undesirable odors and / or odors originating from the formulations can be carried out using methods known in the art. Exemplary methods include, but are not limited to, vapor pressure measurement and / or gas chromatography for detecting and / or identifying organic compounds known to exhibit undesirable odors and / or odors.

[0164] For example, a reduction in the vapor pressure of a formulation correlates with a reduction in the undesirable odor and / or odor of that particular formulation. Therefore, in some embodiments, the formulations disclosed herein exhibit a vapor pressure reduction of at least about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, and about 55% compared to commercially available formulations (e.g., Eco Argo's NEON® product family).

[0165] Devices for measuring and identifying undesirable odors and / or smells may also be used. Exemplary devices include odor meters and electronic noses capable of electronically "smelling" undesirable odors and / or smells (see, for example, U.S. Patent No. 10,603,858, which is incorporated herein by reference in its entirety). For example, an exemplary method for using a device such as an electronic nose for detecting undesirable odors and / or smells may include placing the formulation disclosed herein into a sealed container, sealing the container for a certain period of time, reopening the container, and electronically smelling the formulation with an electronic nose, the step of electronically smelling with an electronic nose may be performed to determine whether the formulation has a sulfurous odor. In some embodiments, the container may be exposed to elevated temperatures during the sealing step. In some embodiments, electronically olfactory detection includes drawing an airborne object into a sample chamber that detects airborne particles using multiple sensors, processing data from the multiple sensors to determine whether any of the airborne particles are airborne particles of the formulation, and indicating the presence and / or amount of airborne particles of the formulation present.

[0166] Accordingly, in some embodiments, the formulations disclosed herein exhibit a response rate reduction of at least about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, and 50% compared to the response rates of commercially available formulations (e.g., Eco Argo's NEON® product family).

[0167] III. Agricultural composition Any of the nitrogen-stabilizing compositions and / or formulations described may be combined with one or more other components selected from the group consisting of fertilizers, agriculturally active compounds, seeds, pesticides, herbicides, insecticides, fungicides, acaricides, etc.

[0168] In some embodiments, the described nitrogen-stabilizing composition and / or formulation may be mixed with a fertilizer product, applied as a surface coating to the fertilizer product, or otherwise completely mixed with the fertilizer product. In some embodiments, in such combined fertilizer / nitrogen-stabilizing composition products, the fertilizer is in the form of particles having an average diameter of about powder size (less than about 0.001 cm) to about 10 mm, more preferably about 0.1 mm to about 5 mm, and even more preferably about 0.15 mm to about 3 mm. The nitrogen-stabilizing composition and / or formulation may be present in such combined products at levels of about 0.001 g to about 20 g per 100 g of fertilizer, about 0.01 to about 7 g per 100 g of fertilizer, about 0.08 g to about 5 g per 100 g of fertilizer, or about 0.09 g to about 2 g per 100 g of fertilizer. In the case of combined fertilizer / nitrogen-stabilizing composition products, the combined product can be applied at levels such that the amount of nitrogen-stabilizing composition and / or formulation applied is approximately 10 to 150 g per acre of soil, approximately 30 to 125 g per acre, or approximately 40 to 120 g per acre of soil. The combined product can also be applied as a liquid dispersion or as a dry granular product, at the discretion of the user. When the nitrogen-stabilizing composition and / or formulation is used as a coating, the nitrogen-stabilizing composition and / or formulation may contain approximately 0.005% to 15% by weight of the coated fertilizer product, approximately 0.01% to 10% by weight of the coated fertilizer product, approximately 0.05% to 2% by weight of the coated fertilizer product, or approximately 0.5% to 1% by weight of the coated fertilizer product.

[0169] A. Fertilizer In some embodiments, the agricultural product is a fertilizer. The fertilizer may be a solid fertilizer, such as granular and / or prill-like fertilizers, and the nitrogen-stabilizing composition and / or formulation may be applied to the fertilizer as a liquid dispersion or mixed with the fertilizer. The fertilizer may also be in a semi-solid form (e.g., manure) in which the nitrogen-stabilizing composition and / or formulation may be applied to the fertilizer as a liquid dispersion or mixed with the fertilizer. The fertilizer may be in liquid form, and the nitrogen-stabilizing composition and / or formulation may be mixed with the liquid fertilizer.

[0170] In some embodiments, the fertilizer is ammonia containing urea and / or anhydrous ammonia fertilizer, or contains them. In the case of liquid fertilizers such as UAN, the nitrogen stabilizing composition and / or formulation is usually mixed with the fertilizer liquid in appropriate amounts. In liquid fertilizers containing urea, urea is usually present at a level of about 1 to about 12 mol / L, more preferably about 2 to about 10 mol / L. Another alternative would be to impregnate urea or a urea-containing fertilizer together with the nitrogen stabilizing composition during the manufacture of such a product. The composition should contain urea in some form, but other types of fertilizers may be used in the agricultural composition.

[0171] Such additional secondary fertilizers may be selected from the group consisting of starter fertilizers, phosphate fertilizers, nitrogen-containing fertilizers, phosphorus-containing fertilizers, potassium-containing fertilizers, calcium-containing fertilizers, magnesium-containing fertilizers, boron-containing fertilizers, chlorine-containing fertilizers, zinc-containing fertilizers, manganese-containing fertilizers, and / or copper-containing fertilizers. In some embodiments, the additional fertilizer contains nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, or micronutrients available to the plant. In some embodiments, the fertilizer is solid, granular, a fluid suspension, a gas, or a solutionized fertilizer. In some embodiments, the fertilizer contains micronutrients, which are essential elements that plants require in small amounts. In some embodiments, the fertilizer contains metal ions selected from the group consisting of Fe, Mn, Mg, Zn, Cu, Ni, Co, Mo, V, and Ca. In some embodiments, the fertilizer contains gypsum, a member of the xerite group, potassium products, magnesium potassium sulfate, elemental sulfur, or magnesium potassium sulfate. Such fertilizers may be granular, liquid, gas, or a mixture (e.g., a suspension of solid fertilizer particles in a liquid material). In some embodiments, the additional fertilizer is an NPK fertilizer.

[0172] Generally, the amount of such secondary fertilizer will be less than the amount of urea fraction. Such double fertilizer compositions containing the nitrogen stabilizer compositions disclosed herein may be used in the exact same manner and in the same amounts as the corresponding urea fertilizer products for application to fields and / or crops. In the case of solid or semi-solid products, the products may be applied in the same amounts before, during, or after planting by broadcast, deep or subsurface placement, local placement, contact, band, hill, and row placement. Liquid compositions will typically be applied by incorporating the liquid into the soil by knife-in or other conventional methods.

[0173] When the nitrogen stabilizer composition or preparation thereof described herein is applied together with the application of one or more fertilizers, the nitrogen stabilizer composition may be applied before, after, or simultaneously with the application of the fertilizers.

[0174] As described above, fertilizer compositions containing nitrogen stabilizer compositions and / or formulations disclosed herein can be applied in any manner that benefits the crop of interest. In some embodiments, such compositions are applied to or to the entire growth medium before sowing or transplanting the desired crop plant. In some embodiments, the compositions can be applied to the rhizosphere of a growing plant.

[0175] B. Seeds In some embodiments, agricultural seeds are coated with one or more of the nitrogen stabilizer compositions and / or formulations described. The nitrogen stabilizer compositions and / or formulations may be present in the seed product at levels of about 0.001–10%, about 0.004%–2%, about 0.01%–about 1%, or about 0.1%–about 1% by weight (or about 10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about 3%, about 2%, about 1%, about 0.5%, about 0.1%, about 0.01% or less, or about 0.001% or less) based on the total weight of the coated seed product. The seeds may be, but are not limited to, wheat, barley, oats, triticale, rye, rice, maize, soybeans, cotton, or rapeseed.

[0176] C. Others In some embodiments, pesticides, herbicides, insecticides, fungicides, and / or acaricides are described in combination with one or more of the nitrogen stabilizer compositions and / or formulations described herein. As used herein, “pesticide” means any agent having pesticide activity (e.g., herbicides, insecticides, fungicides), preferably selected from the group consisting of insecticides, herbicides, and mixtures thereof, but usually excluding materials claimed to have plant fertilizing properties, such as sodium borate, and zinc compounds such as zinc oxide, zinc sulfate, and zinc chloride. For a non-limiting list of pesticides, see the “Farm Chemicals Handbook 2000, 2004” (Meister Publishing Co, Willoughby, OH), which is incorporated herein by reference in its entirety.

[0177] Examples of herbicides include, but are not limited to, acetochlor, arachlor, aminopyralide, atrazine, benoxacol, bromoxynil, carfentrazone, chlorsulfuron, clodinahop, clopyralide, dicamba, diclohop-methyl, dimethenamide, phenoxaprop, flucarbazone, flufenacet, flumetulam, flumicrolac, fluroxypyr, glufosinate-ammonium, glyphosate, halosulfuron-methyl, imazametabent, imazamox, imazapyr, imazakine, imazetapyr, isoxaflutol, and quinchlorate. Examples include MCPA, MCPamine, MCPester, mephenoxam, mesotrione, metrachlor, s-methrachlor, metrivudine, metosulfuron-methyl, nicosulfuron, paraquat, bendimethalin, picloram, primisulfuron, propoxycarbazone, prosulfuron, pyraflufenethyl, limsulfuron, simazine, sulfosulfuron, thifensulfuron, topramezone, tralcoxidime, triallate, triasulfuron, tribenulon, triclopyr, trifluralin, 2,4-D, 2,4-Damine, and 2,4-D ester.

[0178] Examples of insecticides, though not limited to these, include 1,2-dichloropropane, 1,3-dichloropropene, abamectin, acephate, acequinosyl, acetamiprid, acetylone, acetoprole, acrinatrin, acrylonitrile, alanicarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, allylxycarb, alphacypermethrin, alphaecdysone, amidithione, amidoflumet, aminocarb, amiton, amitraz, anabasine, arsenic oxide, atidathion, azadirachtin, azamethiphos, and adinphos. Ethyl, azinophosphate-methyl, azobenzene, azocyclotin, azothoate, barium hexafluorosilicate, bartholin, bencrotiaz, bendiolab, benfuracarb, benoxaphos, bensultap, benzoximate, benzyl benzoate, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, binapacril, biorethrin, bioetanomethinine, biopermethrin, bistriflurone, borax, boric acid, bromofenbinphos, bromoDDT, bromocyclene, bromophos, bromophosethyl, bromopropyl Bufencarb, buprofezin, butacarb, butathiophos, butocarboxime, butonate, butoxycarboxime, kazusaphos, calcium arsenate, polysulfide calcium, campechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, cartap, quinomethionate, chlorantraniliprole, chlorbenside, chlorbicyclene, chlordane, chlordecone, chlordimeform, chlorethoxyphos, chlorfenapyr, chlorphenetol, chlorfensone, chlorfensone, chlorfenside Rolfen sulfide, chlorfenbinfos, chlorfluazuron, chlormefos, chlorobenzilate, chloroform, chloromebform, chloromethiurone, chloropicrin, chloropropylate, chlorphoxime, chlorprazofos, chlorpyrifos, chlorpyrifos methyl, chlorthiofos, chromafenozide, synerin I, synerin II, cismethrin, chloetocarb, clofentezine, closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate, coumaphos, cumitoate, crotamiton, clotoxyfos,Cluentalen A and B, clufomate, cryolite, cyanophenphos, cyanophos, cyanthoate, ciclethrin, cycloprothrin, cyenopyrafen, cyflumetofen, cyfluthrin, cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyromazine, cythioate, d-limonene, dazomet, DBCP. DCIP, DDT, decarbofuran, deltamethrin, demefion, demefion O, demefion S, demeton, demeton methyl, demeton O, demeton O methyl, demeton S, demeton S methyl, demeton S methylsulfone, diafenthiuron, dialiphos, diamidaphos, diazinon, dicapton, diclofenthion, diclofluanide, dichlorvos, dicofol, dicresil, diclotophos, dicyclanil, dieldrin, dienochlor, diflovidazine Diflubenzuron, Dirol, Dimefluthrin, Dimehox, Dimethane, Dimethoate, Dimethrin, Dimethylvinphos, Dimethilane, Dinex, Dinobutone, Dinocap, Dinocap 4, Dinocap 6, Dinoctone, Dinopenton, Dinoprop, Dinosam, Dinosulfone, Dinotefuran, Dinotervon, Diphenolane, Dioxabenzophos, Dioxacarb, Dioxathion, Diphenylsulfone, Disulfiram, Disulfone, Diticlophos, DNOC, Dophena Pin, doramectin, ecdysterone, emamectin, EMPC, empenthrin, endosulfan, endothione, endrin, EPN, epophenonane, eprinomectin, esfenvalerate, etaphos, ethiofencarb, ethione, ethiprole, etoatemethyl, etoprophos, ethyl DDD, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, etofenprox, etoxazole, etrimphos, EXD, Fanfa, fenamicol S, phenazaflor, phenazaquin, fenbutatin oxide, fenchlorphos, phenetacarb, fenfluthrin, fenitrothion, phenobucarb, phenothiocarb, phenoxacrim, phenoxycarb, fenpyritrin, fenpropathrin, fenpyroximate, fenson, phensulfotion, fenthion, fenthion ethyl, fentriphanil, fenvalerate, fipronil, flonicamide, fluacrypyrim, fluazuron,Flubendiamide, flubendimine, flucoflon, flucycloxlon, flucisline, fluenetil, fluphenelim, flufenoxlon, flufenprox, flumethrin, fluolbenside, fluvalinate, honofos, formmethanate, formothion, formparanate, fosmethilane, fosspire, fosthiazate, fosthiethane, fosthiethane, flatiocarb, fretrin, furfural, gamma-cyhalotrin, gamma-HCH, halfemprox, halophenozide, HCH, HEOD, heptachlor, heptenofos, Heterophos, Hexaflumurone, Hexythiazox, HHDN, Hydramethylnon, Hydrocyanide, Hydroprene, Hikincarb, Imisiaphos, Imidacloprid, Imiprothrin, Indoxacarb, Iodomethane, IPSP, Isamidophos, Isazofos, Isobenzane, Isocarbophos, Isodrine, Isofenphos, Isoprocarb, Isoprothiolane, Isothioate, Isooxathion, Ivermectin, Jasmolin I, Jasmolin II, Jodofenphos, Juvenile Hormone I, Juvenile Hormone II, Juvenile Hormone III, Kereban, Quino Prene, lambda cyhalotrin, lead arsenate, lepimectin, leptophos, lindane, lilimphos, lufenulon, ritidathion, malathion, malonoben, magidoc, mecaban, mecafone, menazone, mephosphoran, mercury chloride, mesulfen, mesulfenphos, metaflumizone, metam, methacryphos, methamidophos, methidathion, methiocarb, metochlortophos, methomyl, methoprene, methoxychlor, methoxyphenozide, methyl bromide, methyl isothiocyanate, methylchloroform, methylene chloride, metofluthrin, metocarb, metox Sadiazone, Mevinphos, Mexacarbate, Milbemectin, Milbemycin oxime, Mipahox, Myrex, MNAF, Monoclotophos, Morphothion, Moxidectin, Naphthalophos, Nared, Naphthalene, Nicotine, Niflulidide, Nicomycin, Nitenpyram, Nichiazine, Nitrilacarb, Novalon, Noviflumuron, Omethoate, Oxamyl, Oxidemetonmethyl, Oxideprophos, Oxydisulfone, Paradichlorobenzene, Parathion, Parathionmethyl, Penflurone, Pentachlorophenol, Permethrin,Fencapton, Phenothrin, Fenthoate, Phorate, Fosalon, Phosphane, Phosmet, Fosnichlor, Phosphamidone, Phosphine, Phosphocarb, Foxim, Foximmethyl, Pyrimethraphos, Pyrimicarb, Pyrimiphosethyl, Pyrimiphosmethyl, Potassium arsenite, Potassium thiocyanate, pp'DDT, Prallethrin, Precosen I, Precosen II, Precosen III, Primidophos, Proclonol, Profenophos, Profluthrin, Promacil, Promecarb, Propaphos, Propargit, Propetamphos, Propoxar, Protidathion, Prothiofos, Protoate, Protifenbut, Piraclofos, Pirafluprole, Pirazofos, Pyrethmetrin, Pyrethrin I, Pyrethrin II, Pyridaben, Pyridaryl, Pyridafenthion, Pyrifluquinazon, Pyrimidifen, Pyrimitate, Pyriprole, Pyriproxyfen, Cassia, Quinalfos, Quinalfos, Quinalfos-methyl, Quinotion, Quinatify (quantifies), Lafoxanide, Resmethrin, Rotenone, Lianya, Sabadilla, Shuradan, Selamectin, Silafluofen, Arsenite Thorium, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sofamide, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramato, sulcoflon, sulfiram, sulfuramide, sulfotep, sulfur, sulfuryl fluoride, sulprophos, taufluvalinate, tadimucarb, TDE, tebufenozide, tebufenpyrad, tebupyrinphos, teflubenzuron, tefluthrin, temephos, TEPP, terarethrin, terbuphos, tetrachloroethane, tetrachlorvinphos, tetradiphon Tetramethrin, tetranactin, tetrasul, thetacypermethrin, thiacloprid, thiamethoxam, ticlophos, thiocarboxim, thiocyclam, thiodicarb, thiophanox, thiometon, thionazine, thioquinox, thiosultap, thuringensin, tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, triaten, triazamate, triazophos, trichlorfon, trichlormetaphos-3, trichloronat, triphenophos, triflumulone, trimetacarb, triprene, bamidthion,Examples include bamidthione, vaniliprole, vaniliprole, XMC, xylcarb, zetashipermethrin, and zolaprofos.

[0179] Examples of bactericides include, but are not limited to, acibenzoral, acyl amino acid bactericides, acipetac, algimorph, aliphatic nitrogen bactericides, allyl alcohol, amide bactericides, ampropylphos, anilazine, anilide bactericides, antibiotic bactericides, aromatic bactericides, aureofungin, azaconazole, azoxystrobin, barium polysulfide, venalaxyl, venalaxyl-M, benodanil, benomyl, benquinox, bentallon, bentiavaricarb, benzalkonium chloride, benzamacryl, benzamide bactericide, benzamorph, benzanilide bactericide, benzimidazole bactericide, benzimidazole bactericide, bethoxazine, binapacril, biphenyl, bitertanol, bithionol, bixafen, blasticidine-S, and bolus. Do mixture, boric acid, boscalid, cross-linked diphenyl fungicide, bromconazole, bupirimate, Burgundy mixture, butthiobate, sec-butylamine, polysulfide calcium, captan, carbamate, carbamorph, carvanilate fungicide, carbendazim, carboxyne, carpropamide, carvon, cheshant mixture, quinomethionato, clobentiazon, chloraniformethane, chloranil, chlorphenazole, chlorodinitronaphthalene, chloroform, Chloroneb, chloropicrin, chlorothalonil, chlorquinox, clozolinate, cyclopirox, climazole, cloto (triazole), copper(II) acetate, copper(II) carbonate, basic, bactericide copper, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper(II) sulfate, copper sulfate, basic, copper zinc chromate, cresol, cufraneb, cuprobum, cuprous oxide, cyazofamide, cyclafamide, cyclic dithiocarbamate bactericide, cycloheximide, cyflufe Namide, cymoxanil, cypendazole, cyproconazole, cyprodinil, dazomet, DBCP, debacarb, decafentin, dehydroacetic acid, dicarboxymide, diclobutazole, diclosimen, diclomazine, dichloran, diethofencarb, diethyl pyrocarbonate, difenoconazole, diflumethrimol, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinitrophenol fungicide, dinovton, dinocap,Dinocap-4, Dinocap-6, Dinoctone, Dinopenton, Dinosulfone, Dinotervon, Diphenylamine, Dipyrithione, Disulfira Fungicide, DNOC, Dodemorph, Dodzine, Dodin, Donatodin, Dorazoxolone, Edifenphos, Epoxyconazole, Etaconazole, Etem, Esaboxum, Ethyrimol, Ethoxyquin, Ethylene Oxide, Ethylmercury 2,3-Dihydroxypropyl Mercaptide, Ethylmercury Acetate, Ethylmercury Bromide, Ethylmercury, Etridiazole, Famoxadone, Phenamidon, Phenaminos Ruf, phenapanil, phenarimol, fenbuconazole, fenflam, fenhexamide, fenitropan, phenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fentin, ferubam, ferimzon, fluazinam, fluoxastrobin, fluquinconazole, flucilazole, flusulfamide, flutolanil, flutriafoll, fraxapyroxad, folpet, formaldehyde, fosetil, fuberidazole, flaxyl, flametopyr, flamide fungicide, flanilide fungicide, flucarbanil, f Luconazole, fluconazole-cis, furfural, flumecyclox, flofanate, gliodin, griseofulvin, guazatin, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorobutadiene, hexachlorobutadienehimexazole, imazalil, imibenconazole, imidazole fungicide, iminooctadine, inorganic fungicide, inorganic mercury fungicide, iodomethane, ibuconazole, iprobenphos, iprodione, iprovalicarb, isopropyl alcohol, isoprothiolane, isovaledion, isopyraz Mu, Kasugamycin, Ketocon), Mancopper, Mancozeb, Maneb, Mebenil, Mecarbinzide, Mepanipyrim, Mepronil, Mercury Chloride (discontinued), Mercury Oxide (discontinued), Mercury Chloride (discontinued), Metalaxyl, Metalaxyl-M (also known as Mephenoxam), Metam, Metazoxolone, Metconazole, Metasulfocarb, Metofloxam, Methyl Bromide, Methyl Isothiocyanate, Methylmercury Benzoate, Dicyandiamide Methylmercury, Pentachlorophenoxide Methylmercury, Methylam, Metminostrobin, Metraphenone, Methosulfovax, Milneb,Morph-p-toluenesulfonanilide, Nabam, Natamycin, Nystatin, β-nitrostyrene, nitrotar-isopropyl, Nualimol, OCH, Octylinone, Ofrace, Oprodione, Organic mercury fungicide, Organic phosphorus fungicide, Organic tin fungicide (discontinued), Orthophenylphenol, Oli, Oxazole fungicide, Oxine copper, Oxpoconazole, Oxcarboxyne, Pefurazoate, Penconazole, Pencyclon, Pentachlorophenol, Penthiopyrad, Phenymercury urea, Phenymercury acetate, Phenymercury chloride, Pheny Mercury derivatives pyrocatechol, phenylmercury nitrate, phenylmercury salicylate, phenyl fungicides, picoxithrobin, piperalin, polycarbamate, high molecular weight dithiocarbamate fungicides, polyoxin, polyoxolim, polysulfide fungicides, potassium azide, polysulfide potassium, potassium thiocyanate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazide, prothiocarb, prothioconazole, pyracarboride, pyraclostrobin, pyrazole fungicides, pyrazophos, pyri Zin fungicides, pyridinitrile, pyrifenox, pyrimethanil, pyrimidine, quinacetol, quinazamide, quinconazole, quinoline fungicides, quinomethionate, quinone fungicides, quinoxaline fungicides, quinoxyfen, quintozen, ravenzazole, salicylanilide, silthiofame, silver, simeconazole, sodium azido, sodium bicarbonate[2][3], sodium polysulfide, spiroxamine, streptomycin, strobilurin fungicides, sulfonanilide fungicides, sulfur, sulfuryl fluoride, sulfotene, TCMTB, tebuconazole, tecronazole Phthalam, Technazen, Tecolam, Tetraconazole, Thiabendazole, Thiadifluoro, Thiazole fungicide, Thiabendazole thiochlorfenfim, Thiomersal, Thiophanate, Thiophanate-methyl, Thiofen fungicide, Thioquinox, Thyram, Thiazinyl, Thioximide, Tibedo, Tolcrophos-methyl, Tolnaftate, Tolfluanide, Tolyl mercury acetate, Triadimephone, Triadimenol, Triamiphos, Trialimol, Triazbutyl, Triclamide, Tricyclazole, Tridemorph, Trifloxystrobin,Examples include triflumizole, triforin, triticonazole, unclassified fungicides, undecylenic acid, uniconazole, uniconazole-P, urea fungicides, validamycin, ballinamide fungicides, vinclozoline, voriconazole, and / or zoxamide.

[0180] Examples of acaricide classes include plant-based mite control agents, cross-linked diphenyl mite control agents, carbamate mite control agents, oximecarbamate mite control agents, carbadic acid mite control agents, dinitrophenol mite control agents, formamidine mite control agents, isoxaline mite control agents, macrocyclic lactone mite control agents, avermectin mite control agents, milbemycin mite control agents, milbemycin mite control agents, mite growth regulators, organochlorine mite control agents, organophosphate mite control agents, organothiophosphate mite control agents, phosphonic acid mite control agents, phosphoa Examples of mite control agents include, but are not limited to, lumidthiolate-based mite control agents, organothin-based mite control agents, phenylsulfonamide-based mite control agents, pyrazole carboxamide-based mite control agents, pyrethroid ether-based mite control agents, quaternary ammonium-based mite control agents, euryrotoid ester-based mite control agents, pyrrole-based mite control agents, quinoxaline-based mite control agents, methoxyacrylate strobilurin-based mite control agents, teronic acid-based mite control agents, thiazolidin-based mite control agents, thiocarbamate-based mite control agents, thiourea-based mite control agents, and unclassified mite control agents. Examples of these classes of acaricides include, but are not limited to, plant-based mite control agents (carvacrol, sanguinalin), and cross-linked diphenyl mite control agents (azobenzene, benzoximate, benzyl, benzoic acid, bromopropylate, chlorbenside, chlorphenetol, chlorfensone, chlorfen sulfide, chlorobenzylate, chloropropylate, cyflumetofen, DDT, dicofol, diphenyl, sulfone, dofenapine, fensone, fentriphanil, fluolbenside, genitol, hexachlorophene, fenproxide, proclonor). (Tetradifone, Tetrasul), Carbamate mite control agents (Benomyl, Carbanolate, Carbaryl, Carbofuran, Methiocarb, Metocarb, Promacil, Propoxar), Oxime carbamate mite control agents (Aldicarb, Butocarboxime, Oxamyl, Thiocarboxime, Thiofanox), Carbazate mite control agents (Bifenazate), Dinitrophenol mite control agents (Binapacril, Dynex, Dinobuton, Dinocap, Dinocap-4, Dinocap-6, Dinoctone, Dinopenton, Dinosulfone, Dinotervon, DNOC),Formamidine mite control agents (amitraz, chlorodimeform, chloromebform, formmethanate, formparanate, medimeform, semiamitraz), isoxazoline mite control agents (afoxolaner, fluralaner, rotilaner, sarolaner), macrocyclic lactundan mite control agent (tetranactin), avermectin mite control agents (abamectin, doramectin, eprinomectin, ivermectin, selamectin), milbemycin mite control agents (milbemectin, milbemycin, oxime, moxidectin), mite growth regulator (clofentezine) , cyromazine, diflovidazine, dofenapine, fluazuron, flubendimine, flucycloxuron, flufenoxuron, hexythiazox), organochlorine mite control agents (bromocyclene, campechlor, DDT, dienochlor, endosulfan, lindane), organophosphate mite control agents (chlorfenvinphos, clotoxyphos, dichlorvos, heptenophos, mevinphos, monoclotophos, nared, TEPP, tetrachlorvinphos), organothiophosphate mite control agents (amidithion, amiton, azinphos-ethyl, azinphos-methyl, azothoethone Benoxaphos, Bromophos, Bromophos-ethyl, Carbophenothion, Chlorpyrifos, Chlorthiophos, Coumaphos, Cyanthate, Demeton, Demeton-O, Demeton-S, Demeton-Methyl, Demeton-O-Methyl, Demeton-S-Methyl, Demeton-S-Methylsulfone, Dialiphos, Diazinon, Dimethoate, Dioxathion, Disulfon, Endothion, Ethion, Ethoate-methyl, Formocion, Malathion, Mekabam, Methacryphos, Omethoate, Oxydeprophos, Oxydisulfon, Parathion, Fencap Ton, phorate, phosalon, phosmet, phostin, phoxim, pirimiphosmethyl, protidathion, protoate, pyrimitate, quinalphos, quinthiophos, sofamide, sulfotep, thiometon, triazophos, triphenophos, bamidothion), phosphonic acid mite control agents (trichlorfon), phosphoramide thioate mite control agents (isocarbofos, methamidophos, propethamphos), phosphorodiamide mite control agents (dimehox, mipahox, shuradan), organostalt mite control agents (azocylotine, cyhexatine, fenbutine, oxide,Phosphate (phenylsulfamide mite control agent) (diclofluanide), phthalimide mite control agent (dialyphos, phosmet), pyrazole mite control agent (cyenopyrafen, fenpiroximate), phenylpyrazole mite control agent (acetol, fipronil, vaniliprole), pyrazole carboxamide mite control agent (piflubmid, tebufenpyrad), pyrethroid ester mite control agent (acrinatrin, bifenthrin, broflusrinate, cyhalotri) (Pyromethrin, alpha-cypermethrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate, tau-fluvalinate, permethrin), pyrethroid ether mite control agent (halfenprox), pyrimidinamine mite control agent (pyrimidifen), pyrrole mite control agent (chlorfenapyr), quaternary ammonium mite control agent (sanguinalin), quinoxalin mite control agent (kinomethionato, thioquinox), methoxymethionine Cyanamide stobilin mite control agents (Bifjunji, fluacrypyrim, fluphenoxystrobin, pyriminostrobin), sulfite ester mite control agents (Aramite, Propargit), tetronic acid mite control agent (spirodiclofen), tetradine mite control agents (clofentezine, diflovidazine), thiazolidinedione mite control agents (flubendimin, hexythiazox), thiocarbamate mite control agent (phenothiocarb), thiourea mite control agent (clo Examples include lomethiuron, diafenthiuron, and unclassified acaricides (acekinosyl, acinonapyr, amidoflumet, arsenic, oxide, clenpyrin, closantel, crotamiton, cycloplate, simiasol, disulfiram, etoxazole, phenazaflor, phenazaquin, fluenetil, mesulfen, MNAF, niflulidide, nikkomycin, pyridaben, sulfiram, sulfuramide, sulfur, thuringensin, triatene).

[0181] In some embodiments, the acaricides also include abamectin, acephate, acequinosyl, acetamiprid, aldicarb, arethrin, aluminum phosphide, aminocarb, amitraz, azadirachtin, azinphos-ethyl, azinphos-methyl, Bacillus thuringiensis, benziocarb, beta-cyfluthrin, bifenazate, bifenthrin, bomil, buprofezin, calcium cyanide, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, chlorfenbinphos, chlorobenzylate, chloropicrin, chlorpyrifos, clofentezin, chlorfenapyr, clothianidin, coumaphos, clotoxyphos, clotoxyphos + dichlorvos, and cryolite. Cyfluthrin, Cyromazine, Cypermethrin, DEET, Deltamethrin, Demeton, Diazinon, Diclofenthion, Dichloropropene, Dichlorvos, Dicofor, Diclotophos, Dierdrin, Dienochlor, Diflubenzuron, Dikar (fungicide + acaricide), Dimethoate, Dinocap, Dinotefuran, Dioxathion, Disulfon, Emamectin Benzoate, Endosulfan, Endrin, Es Fenvalerate, Ethion, Etoprop, Ethylene Dibromide, Ethylene Dichloride, Ethoxazole, Famflu, Fenitrothion, Phenoxycarb, Fenpropathrin, Fenpyroximate, Fensulfothion, Fenthion, Fenvalerate, Flunicamide, Flucitrinate, Fluvalinate, Honofos, Formetanate Hydrochloride, Gamma-Cyhalotrin, Halofenozide, Hexakis, Hexythiazox, Hydramethyl Non, hydrated lime, indoxacarb, imidacloprid, kerosene, quinoprene, lambda-cyhalothrin, lead arsenate, lindan, malathion, mephospholane, metaldehyde, metam-sodium, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyphenozide, methyl bromide, methylparathion, mevinphos, mexacarbate, Milky Disease SporeSpores), Nared, Naphthalene, Nicotine Sulfate, Novalon, Oxamyl, Oxidemeton-methyl, Oxythioquinox, Para-dichlorobenzene, Parathion, PCP, Permethrin, Petroleum, Phorate, Phosalon, Phosphane, Phosmet, Phosphamidone, Foxim, Piperonyl Butoxide, Pyrimicalb, Pyrimiphos-methyl, Profenofos, Propargit, Propetamphos, Propoxar, Pymetrozine, Pyretroid - Synthetic: See Allethrin, Pe The following may be selected: lumethrin, fenvalerate, resmethrin, pyrthium, pyridaben, pyriproxyfen, resmethrin, rotenone, s-methoprene, soap, pesticides, sodium fluoride, spinosad, spiromesifen, sulfotep, sulprofos, temefos, terbufos, tetrachlorvinfos, tetrachlorvinfos + dichlorvos, tetradiphon, thiamethoxam, thiodicarb, toxafen, tralomethrin, trimetacarb, and tebufenozide.

[0182] The amount of nitrogen-stabilizing composition in an agricultural composition containing additional activators (e.g., pesticides, herbicides, insecticides, fungicides, and / or acaricides) can vary. In some embodiments, the amount of nitrogen-stabilizing composition is present at a level of about 0.05% to about 10% by weight (preferably about 0.1% to about 8% by weight, more preferably about 0.1% to about 4% by weight, and most preferably about 0.2% to about 2% by weight) based on the total weight of the agricultural composition containing the additional activators taken as 100% by weight.

[0183] V. Method In some embodiments, nitrogen-stabilizing compositions and / or formulations are used directly. In other embodiments, nitrogen-stabilizing compositions are formulated in a manner that facilitates their use in the context of productive agriculture. The nitrogen-stabilizing compositions used in these methods include the nitrogen stabilizer components and cyclic organic acid anhydride components described above. The nitrogen-stabilizing compositions may be used in the following ways: A. Methods for improving plant growth and / or soil fertility. B. Methods for inhibiting nitrification, urease degradation, or ammonia release or generation. C. Methods for improving soil conditions D. Methods to improve crop yield E. Method for preparing nitrogen-stabilized compositions F. Method for preparing a nitrogen-stabilized composition formulation.

[0184] A. Methods for improving plant growth include contacting soil with a nitrogen-stabilizing composition or formulation containing a nitrogen-stabilizing composition as disclosed herein. In some embodiments, the nitrogen-stabilizing composition or formulation is applied to the soil before the emergence of the planted crop. In some embodiments, the nitrogen-stabilizing composition or formulation is applied to the soil adjacent to the plant, and / or to the base of the plant, and / or to the root zone of the plant.

[0185] Methods for improving plant growth can also be achieved by applying a nitrogen-stabilizing composition or a formulation containing a nitrogen-stabilizing composition disclosed herein to seeds as a seed coating in the form of a liquid dispersion that forms a dry residue upon drying. In these embodiments, the seed coating provides the nitrogen-stabilizing composition in close proximity to the seed at planting time, so that the nitrogen-stabilizing composition can exert its beneficial effects in the environment where it is most needed. That is, the nitrogen-stabilizing composition provides an environment that helps improve plant growth in an area where the effect can be localized around the plant in which the effect is desired. In the case of seeds, a coating containing a nitrogen-stabilizing composition provides an enhanced opportunity for seed germination, subsequent plant growth, and increased availability of nutrients to the plant.

[0186] B. Methods for inhibiting / reducing nitrification, urease degradation, or ammonia release or generation in an affected area include applying a nitrogen-stabilizing composition or a formulation containing a nitrogen-stabilizing composition disclosed herein to the affected area. The affected area may be soil adjacent to plants, fields, pastures, livestock or poultry housing facilities, pet waste, manure collection zones, upright walls forming enclosures, or roofs substantially covering the area, in which case the nitrogen-stabilizing composition may be applied directly to the manure in the collection zone. The methods disclosed herein also aim to inhibit the conversion of urea to ammonia and / or the conversion of ammonia to nitrate, and include applying a nitrogen-stabilizing composition or a formulation containing a nitrogen-stabilizing composition disclosed herein to the affected area. The nitrogen-stabilizing composition is preferably applied in the form of an aqueous dispersion having a pH of about 1 to 5 at a level of about 0.005 to 3 gallons per ton of manure.

[0187] A method for improving soil conditions selected from the group consisting of nitrification processes, urease activity, and combinations thereof, comprising the step of applying an effective amount of the described nitrogen-stabilizing composition or formulation thereof to the soil. In some embodiments, the nitrogen-stabilizing composition is mixed with solid, liquid, or gaseous fertilizers, and in particular solid fertilizers, in the latter case, the nitrogen-stabilizing composition is applied to the surface of the fertilizer as an aqueous dispersion and subsequently dried, so that the nitrogen-stabilizing composition is present on the solid fertilizer as a dried residue. The nitrogen-stabilizing composition is generally applied at a level of about 0.01% to about 10% by weight, based on the total weight of the nitrogen-stabilizing composition / fertilizer product taken as 100% by weight. If the fertilizer is an aqueous liquid fertilizer, the nitrogen-stabilizing composition is added thereto while mixing. The nitrogen-stabilizing composition is preferably in an aqueous dispersion and has a maximum pH of about 3.

[0188] D. Methods for improving crop yield include applying a nitrogen-stabilizing composition or formulation containing a nitrogen-stabilizing composition disclosed herein to an affected area. In some embodiments, the affected area may be a field. In some embodiments, the nitrogen-stabilizing composition or formulation is applied to the soil surrounding a plant, the soil adjacent to the stem of a plant, or to various parts of the plant. In some embodiments, the plant is a maize plant, but should not be limited thereto. In some embodiments, the nitrogen-stabilizing composition or formulation is applied in combination with a fertilizer. In some embodiments, the fertilizer is a nitrogen-containing fertilizer. In some embodiments, the fertilizer contains urea. In some embodiments, the nitrogen-stabilizing composition or formulation is applied before, after, or simultaneously with the application of a nitrogen-containing fertilizer. In some embodiments, the crop yield / harvest yield of plants treated with the nitrogen-stabilizing composition disclosed herein is increased by at least about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, about 80%, about 90%, or at least about 95% compared to untreated plants. In some embodiments, the crop / yield of plants treated with the nitrogen-stabilizing compositions disclosed herein increases by about 50% to about 100%, about 60% to about 95%, about 65% to about 95%, about 65% to about 90%, about 65% to about 80%, or about 70% to about 80% compared to untreated plants. In some embodiments, the nitrogen-stabilizing compositions are applied in combination with urea. In some embodiments, the crop / yield of plants treated with the nitrogen-stabilizing compositions disclosed herein in combination with urea increases by at least about 1%, about 5%, about 8%, about 10%, about 12%, about 14%, about 15%, about 18%, about 20%, about 22%, about 24%, and about 25% compared to plants treated with urea. In some embodiments, the crop / yield of plants treated with the nitrogen-stabilizing compositions disclosed herein in combination with urea increases by about 1% to about 30%, about 1% to about 25%, about 5% to about 25%, about 15% to about 25%, about 20% to about 25%, about 5% to about 20%, or about 5% to about 15% compared to plants treated with urea.

[0189] In some embodiments, the number of rows of grain present in corn cobs of maize plants treated with the disclosed formulations is higher than the number of grain present in corn cobs of untreated maize plants. In some embodiments, the number of rows of grain present in corn cobs of maize plants treated with the nitrogen-stabilizing compositions or formulations disclosed herein is at least about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, or about 80% more than the number of rows of grain present in untreated corn cobs. In some embodiments, the number of rows of grain present in corn cobs of maize plants treated with the nitrogen-stabilizing compositions or formulations disclosed herein is about 10% to about 80%, about 20% to 70%, about 30% to about 60%, or about 40% to about 50% higher than the number of rows of grain present in corn cobs of untreated maize plants.

[0190] In some embodiments, the number of grain rows present in the ears of maize plants treated with the nitrogen-stabilizing compositions or formulations disclosed herein in combination with a nitrogen fertilizer is at least about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, or about 80% higher than the number of grain rows present in the ears of maize plants treated with a nitrogen fertilizer (i.e., urea). In some embodiments, the number of grain rows present in the ears of maize plants treated with the nitrogen-stabilizing compositions or formulations disclosed herein is at least about 10% to about 80%, about 20% to about 70%, about 25% to about 60%, about 30% to about 50%, or about 30% to about 40% higher than the number of grain rows present in the ears of maize plants treated with a nitrogen fertilizer (i.e., urea).

[0191] E. Methods for preparing the nitrogen-stabilized compositions disclosed herein include contacting nitrogen stabilizer components with acid anhydride components. The contact step may be carried out neat or in the presence of a solvent. In some embodiments, the contact step further includes, but is not limited to, a nonpolar solvent such as acetonitrile. In some embodiments, the contact step is carried out at ambient temperature. In some embodiments, the contact step is carried out at high temperatures in the range of about 25°C to about 150°C, about 30°C to about 120°C, about 40°C to about 100°C, about 50°C to about 90°C, or about 60°C to about 80°C. The amounts of nitrogen stabilizer components and acid anhydride components may vary. In some embodiments, the nitrogen stabilizer components and acid anhydride components are present in a molar ratio in the range of about 1:2 to about 2:1.

[0192] F. A method for preparing stabilized formulations of nitrogen-stabilizing compositions is disclosed herein. To prepare the formulations disclosed herein, the method requires the complete solubilization of all components present in the formulation. Methods involving contacting nitrogen-stabilizing components with organic acid anhydride components, which are polymers disclosed herein, in the presence of an aprotic solvent have not been successful in obtaining the desired formulations because all components (particularly the polymers) were not soluble in aprotic solvents at room temperature and high temperatures. Surprisingly, the desired formulations were obtained only when a pre-mixed solution of the polymers present at high concentrations was first prepared, then aliquots were removed from the pre-mixed solution, and then the solution was diluted with an additional aprotic solvent and contacted with the nitrogen-stabilizing composition. It was very surprising and unexpected to find that all components of the nitrogen-stabilizing composition were soluble only when the polymers were first prepared as a pre-mixed solution and then mixed with the nitrogen-stabilizing components.

[0193] Therefore, the method for preparing the formulations disclosed herein is, The process involves mixing the organic acid anhydride components with a first aprotic solvent to form a premixed solution of the organic acid anhydride components, The steps include taking out an aliquot of the pre-mixed solution of organic acid anhydride components, The steps include diluting the extracted aliquots with a second aprotic solvent to obtain an organic acid anhydride solution, The steps include: bringing an organic acid anhydride solution into contact with an amine stabilizer to prepare a stabilized organic acid anhydride solution; The method includes the step of adding nitrogen stabilizer components to a stabilized organic acid anhydride solution to obtain a desired stabilized formulation.

[0194] In some embodiments, the organic acid anhydride component is a polymer disclosed herein. In some embodiments, the first aprotic solvent and the second aprotic solvent are the same. In some embodiments, the first aprotic solvent is DMSO. In some embodiments, the mixing step is carried out at a raised temperature (e.g., above room temperature). In some embodiments, the mixing step is carried out at temperatures in the range of about 30°C to about 200°C, about 40°C to about 175°C, about 50°C to about 150°C, about 60°C to about 125°C, about 70°C to about 100°C, or about 75°C to about 85°C. In some embodiments, the mixing step is carried out at room temperature. Note that the organic acid anhydride component solvates more slowly at room temperature than it does at higher temperatures. In some embodiments, the amount of organic acid anhydride component mixed is in the range of about 5% to about 25% w / w, based on the total weight of the premixed organic acid anhydride component solution.

[0195] In some embodiments, the amount of aliquots of the premixed organic acid anhydride component solution in the extraction step is in the range of about 25% to about 50% w / w, based on the total weight of the premixed organic acid anhydride component solution.

[0196] In some embodiments, the amount of the second aprotic solvent is in the range of about 20% to about 50% w / w, based on the total weight of the stabilized formulation. In some embodiments, the second aprotic solvent is DMSO.

[0197] In some embodiments, the amount of amine stabilizer ranges from about 1% to about 20% w / w, based on the total weight of the stabilized formulation. In some embodiments, the amine stabilizer is monoethanolamine.

[0198] In some embodiments, the nitrogen stabilizer components are urease inhibitors and nitrification inhibitors. In some embodiments, the nitrogen stabilizer components are DCD. In some embodiments, the nitrogen stabilizer components are NBPT.

[0199] In some embodiments, the nitrogen stabilizer components are NBPT and DCD. In such embodiments, the method further comprises sequentially adding DCD and NBPT to a stabilized organic acid anhydride solution. For example, in some embodiments, DCD is added to the stabilized organic acid anhydride solution before NBPT. In some embodiments, the method further comprises cooling the stabilized organic acid anhydride solution after adding DCD and before adding NBPT. In some embodiments, the stabilized organic acid anhydride solution is cooled to about 80°C or below after adding DCD and before adding NBPT.

[0200] The methods disclosed herein also involve preparing stabilization formulations of individual components of a nitrogen-stabilized composition, The steps include: contacting an amine stabilizer with an aprotic solvent to obtain a stabilized aprotic solvent; The preparation method includes the step of adding nitrogen stabilizer components to a stabilized aprotic solvent to produce a stabilized formulation.

[0201] The methods disclosed herein also involve preparing a stabilized formulation containing the organic acid anhydride components disclosed herein, The process involves mixing the organic acid anhydride components with a first aprotic solvent to form a premixed solution of the organic acid anhydride components, The steps include taking out an aliquot of the pre-mixed solution of organic acid anhydride components, The steps include diluting the extracted aliquots with a second aprotic solvent to obtain an organic acid anhydride solution, The preparation method includes the step of contacting an organic acid anhydride solution with an amine stabilizer to obtain a stabilized formulation.

[0202] In some embodiments, methods A, B, and C described above involve contacting a desired area with a nitrogen-stabilizing composition at a rate of about 100 g to about 120 g of the nitrogen-stabilizing composition per acre. In some embodiments, the nitrogen-stabilizing composition may be in solution at a rate of about 0.5 lbs to about 4 lbs per U.S. gallon, or about 1 lb to about 3 lbs per U.S. gallon, or about 2 lbs per U.S. gallon. In some embodiments, the method involves contacting a desired area at a rate of about 0.5 to about 4 qt. / acre, or about 1 to about 2 qt. / acre.

[0203] Specific embodiments of the subject matter described herein include: 1. A nitrogen-stabilizing composition, Nitrogen stabilizer components, and Contains organic acid anhydride components, A nitrogen-stabilizing composition in which the nitrogen stabilizer component is a urease inhibitor and / or a nitrification inhibitor, It is a vehicle, aprotic solvents, and A vehicle containing an amine stabilizer, A stabilized formulation containing the above.

[0204] 2. The stabilized formulation according to Embodiment 1, wherein the nitrogen stabilizer component is N-(n-butyl)thiophosphate triamide (NBPT) and / or dicyanamide (DCD).

[0205] 3. The stabilized formulation according to Embodiment 1 or 2, wherein the organic acid anhydride component is an organic acid anhydride polymer.

[0206] 4. The stabilized formulation according to any of the above embodiments, wherein the organic acid anhydride polymer is a copolymer containing at least two different repeating units, each containing one type B repeating unit and one type C repeating unit.

[0207] 5. The stabilized formulation according to Embodiment 4, wherein the copolymer is a random copolymer.

[0208] 6. The stabilized formulation according to Embodiment 4 or 5, wherein the type B repeating unit is derived from an (un)substituted monomer of maleic anhydride, an (un)substituted monomer of itaconic anhydride, or a combination thereof.

[0209] 7. A stabilized formulation according to any one of Embodiments 4 to 6, wherein the type B repeating unit is derived from an (un)substituted monomer of maleic anhydride.

[0210] 8. A stabilized formulation according to any one of Embodiments 4 to 7, wherein at least about 50 mol% of the repeating units of the organic acid anhydride polymer are type B repeating units.

[0211] 9. A stabilized formulation according to any one of Embodiments 4 to 8, wherein the organic acid anhydride polymer contains a C-type repeating unit derived from an (un)substituted alkene.

[0212] 10. The stabilized formulation according to Embodiment 9, wherein the alkene is selected from ethylene, propylene, butylene, isobutylene, styrene, methyl vinyl ether, and combinations thereof.

[0213] 11. The organic acid anhydride polymer has the structure shown in the following formula: [ka] In the formula, R1, R2, R3, and R4 are independently selected from -H, -COOH, -COOR, -OCOH, -OCOR, -OR, -CN, -SO2R, -SO3R, -COR, -CONH2, -CONHR, -CONR2, -CHO, NO2, halogen-alkyl, -cycloalkyl, -aryl, -alkalyl, or aralkyl, and R is an (un)substituted C1-C8 alkyl group, an (un)substituted C2-C8 alkenyl group, an (un)substituted aryl group, or an (un)substituted heteroaryl group. The stabilized formulation according to any one of claims 3 to 10, wherein n is an integer greater than 2.

[0214] 12. A stabilized formulation according to any of the above embodiments, wherein the aprotic solvent is selected from dichloromethane, dimethylacetamide, dimethylformamide, dimethyl sulfoxide (DMSO), ethyl acetate, acetone, acetonitrile, hexamethylphosphoramide, dimethyl sulfone, sulfolane, 1,3-dimethyl-2-imidazoidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, methyl acetate, ethyl lactate, N-methylpyrrolidone, tetrahydrofuran, and propylene carbonate.

[0215] 13. The stabilized formulation according to any of the above embodiments, wherein the aprotic solvent is dimethyl sulfoxide (DMSO).

[0216] 14. A stabilized formulation according to any of the above embodiments, wherein the amine stabilizer is selected from 1,2-diaminocyclohexane (DCH), bis(hexamethylene)triamine (BHT), monoethanolamine, ethylaminoethanol, dimethylaminoethanol, isopropylaminoethanol, diethanolamine, triethanolamine, methylaminoethanol, aminopropanol, methylaminopropanol, dimethylaminopropanol, aminobutanol, dimethylaminobutanol, aminobutanediol, trihydroxymethylaminoethane, diethylaminopropanediol, 1-amino-cyclopentanemethanol, and aminobenzyl alcohol.

[0217] 15. The stabilized formulation according to any of the above embodiments, wherein the amine stabilizer is monoethanolamine.

[0218] 16. The stabilized preparation according to any of the above embodiments, wherein the nitrogen-stabilizing composition is present in an amount of about 5% to about 50% w / w based on the total weight of the stabilized preparation.

[0219] 17. The stabilized formulation according to any of the above embodiments, wherein the aprotic solvent is present in an amount of about 50% to about 75% w / w based on the total weight of the stabilized formulation.

[0220] 18. The stabilized preparation according to any of the above embodiments, wherein the amine stabilizer is present in an amount of about 3% to about 8% w / w based on the total weight of the stabilized preparation.

[0221] 19. A stabilized preparation according to any of the above embodiments, wherein the nitrogen stabilizer component is present in an amount of approximately 5% to approximately 50% w / w based on the total weight of the stabilized preparation.

[0222] 20. A stabilized preparation according to any of the above embodiments, wherein the nitrogen stabilizer component comprises a urease inhibitor present in an amount of about 5% to about 15% w / w based on the total weight of the stabilized preparation, and a nitrification inhibitor present in an amount of about 5% to about 20% w / w based on the total weight of the stabilized preparation.

[0223] 21. A stabilized preparation according to any of the above embodiments, comprising a nitrogen stabilizer component comprising a urease inhibitor present in an amount of approximately 5% to approximately 15% w / w, a nitrification inhibitor present in an amount of approximately 5% to approximately 20% w / w, an aprotic solvent present in an amount of approximately 50% to approximately 75%, and an amine stabilizer present in an amount of approximately 3% to approximately 8% w / w, wherein all weights are based on the total weight of the stabilized preparation.

[0224] 22. The stabilized formulation according to Embodiment 20 or 21, wherein the urease inhibitor is DCD and the nitrification inhibitor is NBPT.

[0225] 23. The stabilized formulation according to any one of Embodiments 20 to 22, wherein the aprotic solvent is DMSO.

[0226] 24. The stabilized formulation according to any one of embodiments 20 to 23, wherein the amine stabilizer is monoethanolamine.

[0227] 25. An agricultural composition comprising the stabilizing agent and fertilizer described in any one of the above embodiments.

[0228] 26. The agricultural composition according to Embodiment 25, wherein the fertilizer is a urea-containing fertilizer.

[0229] 27. The agricultural composition according to Embodiment 25 or 26, wherein the urea-containing fertilizer is manure.

[0230] 28. An agricultural composition according to any one of embodiments 25 to 27, wherein a urea-containing fertilizer is present at a level of about 1 to about 12 moles / L.

[0231] 29. The agricultural composition according to any one of embodiments 25 to 28, wherein the nitrogen-stabilizing composition is applied to the surface of a fertilizer in the form of an aqueous dispersion.

[0232] 30. A method for inhibiting soil-derived urease enzymes, comprising the step of applying a stabilized formulation described in any one of the above embodiments to soil, wherein the formulation is present in an amount sufficient to inhibit the decomposition of urea by the action of soil-derived urease enzymes.

[0233] 31. A method for fertilizing soil, comprising applying to the soil a stabilizing agent according to any one of claims 1 to 24, or an agricultural composition according to any one of embodiments 25 to 29.

[0234] 32. A method for preparing a stabilized formulation according to any one of Embodiments 1 to 24, The process involves mixing the organic acid anhydride components with a first aprotic solvent to form a premixed solution of the organic acid anhydride components, Taking out an aliquot of the organic acid anhydride component preliminary mixed solution; Diluting the taken-out aliquot with a second aprotic solvent to obtain an organic acid anhydride solution; Contacting the organic acid anhydride solution with an amine stabilizer to prepare a stabilized organic acid anhydride solution; Adding a nitrogen stabilizer component to the stabilized organic acid anhydride solution to obtain a desired stabilized preparation, a method comprising.

[0235] 33. The method according to embodiment 32, wherein the first and second aprotic solvents are DMSO.

[0236] 34. The method according to embodiment 32, wherein the mixing step is carried out at a temperature in the range of about 70 °C to about 100 °C.

[0237] 35. The method according to any one of embodiments 32 to 34, wherein the abundance of the organic acid anhydride component is in the range of about 5% to about 25% w / w based on the total weight of the organic acid anhydride component preliminary mixed solution.

[0238] 36. The method according to any one of embodiments 32 to 35, wherein the amount of the aliquot of the organic acid anhydride component preliminary mixed solution is in the range of about 25% to about 50% w / w based on the total weight of the organic acid anhydride component preliminary mixed solution.

[0239] 37. The method according to any one of embodiments 32 to 36, wherein the amount of the amine stabilizer is in the range of about 1 to about 20% w / w based on the total weight of the stabilized preparation.

[0240] 38. The method according to any one of embodiments 32 to 37, wherein the nitrogen stabilizer component comprises a urease inhibitor and a nitrification inhibitor.

[0241] 39. The method according to embodiment 38, wherein the step of adding the nitrogen stabilizer component comprises sequentially adding a urease inhibitor and a nitrification inhibitor.

[0242] 40. The method according to embodiment 39, wherein the nitrification inhibitor is added before the urease inhibitor.

[0243] 41. The method according to embodiment 40, wherein the addition step further comprises cooling the stabilized organic acid anhydride solution after adding the nitrification inhibitor and before adding the urease inhibitor.

Examples

[0244] Example 1: Preparation of a premixed polymer solution A premixed polymer solution containing 80% w / w dimethyl sulfoxide (DMSO) (heated to 175°F (79°C)) and 20% w / w organic acid anhydride polymer 1 was prepared. First, DMSO was heated to 175°F (79°C) in a stainless steel mixing vessel. The premixed solution was mixed until all the polymers were completely dissolved and a clear solution was observed.

[0245] This premixed polymer solution can be optionally diluted with additional DMSO solvent depending on the formula of the polymer % to be produced.

[0246] Example 2: Preparation of a 5-20-5 (polymer 1 - DCD - NBPT) preparation A 25.0% w / w premixed polymer solution from Example 1 was transferred to a stainless steel heating reactor and the tank was heated to 175°F (79°C). During heating, more than 45% w / w additional DMSO was added to the solution. Then, 5% w / w monoethanolamine (MEA) was added. After addition, a color change to a darker yellow solution was detected. The reaction mixture was mixed for an additional 30 minutes.

[0247] 20% w / w DCD was slowly added to the heated mixing tank. The reaction mixture was continuously mixed for 60 minutes and samples were analyzed to confirm that the DCD was completely dissolved. Once the DCD was dissolved, the solution was cooled to 100°F.

[0248] Finally, 5% w / w NBPT was added to a solution below 100°F (38°C). When mixed, the product turned green. Mixing was continued until a clear, yellow, semi-viscous material was obtained as the final product.

[0249] Following the procedure described above, the formulations shown in Tables 1-3 were prepared.

[0250] [Table 1]

[0251] [Table 2]

[0252] [Table 3]

[0253] [Table 4] TIFF0007858552000017.tif117163* The relative amounts of polymer, DCD, and NBPT are given as % of polymer - % of DCD - % of NBPT. **A "pass" indicates a formulation in which all components are completely soluble and the solution is clear. A "fail" indicates a formulation in which all components are not completely dissolved and the solution is cloudy or precipitates are observed.**

[0254] Example 3: Preparation of 5-20-5 (polymer 1-DCD-NBPT) preparation without using a pre-mixed polymer solution In a stainless steel reactor, 65% w / w DMSO was heated to 175°F (79°C). 5% w / w dry polymer was slowly transferred into the solution. After the addition was complete, the reaction mixture was stirred until all the polymer was completely dissolved and the solution had a clear, straw-yellow appearance. 5% w / w monoethanolamine was added, and the resulting solution turned a darker yellow. The reaction mixture was continued stirring for a further 30 minutes.

[0255] It was slowly added to a heated mixing tank containing 20% w / w DCD. After the addition was complete, the reaction mixture was mixed for 60 minutes, a sample was taken out and tested to confirm that all of the DCD had completely dissolved. Once the DCD had dissolved, the solution was slowly cooled to 100°F (38°C).

[0256] 5% w / w NBPT was added to the cooling solution that was at 100°F (38°C) or lower. When mixed, the product turned green and mixing was continued until a final yellow product was produced.

[0257] Example 4: Field Study of Preparation 5-5-15 Furthermore, a field study was conducted using Preparation 5-5-15. The results of this field study are shown in Figure 1, where corn fields were treated with urea-free, urea-containing fertilizers, and the formulations disclosed herein (having 15% w / w NBPT, 5% w / w DCD, and 5% w / w organic acid anhydride polymer 6 based on the total weight of the formulation) along with urea-containing fertilizers. The application rate of the 15-5-5 formulation was 2 L of the formulation per ton of urea. Figure 1 shows that the corn treated with the urea-containing fertilizer and Formulation 5-5-15 produced the best corn ears with the most corn kernels.

[0258] Example 5: Field Study A field study was conducted in an area under a no-till system where corn was cultivated with rainwater (i.e., without irrigation). The cultivated corn was the corn hybrid AG 8088 VT PRO (high yield) having 100 mL / ha of Standak Top and a plant density of 77,000 plants / ha. The following three formulations were applied to the field at three different amounts (1, 2, and 3 L / m 3 ) Three-component formulation (10-10-10; % of polymer-% of DCD-% of NBPT) Three-component V formulation (5-5-15; % of polymer-% of DCD-% of NBPT) Three-component N formulation (5-20-5; % of polymer-% of DCD-% of NBPT)

[0259] As a control, the plants were treated with only nitrogen fertilizer (e.g., UAN with 30% - 45% N) or left untreated.

[0260] Nitrogen fertilizer was applied at a rate of 135 kg / ha of N corresponding to a rate of 75 N / bu for 10.8 tons / ha of corn. Additionally, a typical herbicide, fungicide, and insecticide program was used to remove any variability in the study due to weeds, diseases, or insects throughout the study period.

[0261] The activity of nitrate reductase at V2 - V3 and at flowering (the first fully developed leaf, 3 plants per section) was measured. Additionally, soil collections were taken for the determination of N - NO3 and N - NH4 until 30 days after the range of applications. This methodology was adapted by Cataldo et al (1975) and Kemper; Zewers (1986). Centro de Fertilidad del Suelo (CEFERT). Growth analysis was performed every 30 days on the dry plant mass. Harvesting was done at physiological maturity. The 3 plants on the central line of each section were harvested, excluding 1.0 meters from each end. The rows were measured, and the number of harvested plants and ears per row was counted. After harvesting, manual threshing was done to determine the mass of 100 grains and the crop yield. The harvest results were estimated for kg / ha and bu / acre.

[0262] The following results were obtained.

[0263]

Table 5

[0264] The harvest results are further shown in Figure 2, which shows that crop yield increased by at least 50% compared to untreated plants and by at least 5% compared to plants treated with UAN. Furthermore, Figure 3 shows that maize ears obtained from maize plants treated with urea (135 kg / ha of N) showed more maize grains compared to untreated ears. Figure 4 shows that maize ears treated with the formulation disclosed in combination with nitrogen fertilizer showed an increase in the amount of maize rows present in the maize ear compared to maize ears left untreated. This is further illustrated in Figure 5, which compares maize ear stalks of all three treatments, and in Figure 6, which compares maize ears treated with the formulation disclosed herein in combination with nitrogen fertilizer with untreated maize ears.

[0265] Example 6: Field studies in various corn-producing areas in the United States. To evaluate the formulations disclosed herein in combination with nitrogen fertilizers in relation to corn growth and harvest under various soil and climatic conditions, field studies were conducted in various locations in the United States, commonly referred to as the U.S. corn region.

[0266] [Table 6] TIFF0007858552000020.tif22155*5-25-0(Polymer 7%-DCD%-NMPT%) [Please check]

[0267] Many of these locations showed increased yields compared to the control group (i.e., plants treated with nitrogen fertilizer only).

[0268] [Table 7]

[0269] Furthermore, it was noteworthy that the amount of nitrogen fertilizer applied to each field in the corn region of various locations in the United States was significantly less than the university-recommended values ​​for each location (see Table 8). While not bound by theory, it is believed that the combination of DCD (nitrification inhibitor) and NBPT (urease inhibitor) in the disclosed formulation minimizes the conversion of urea present in the nitrogen fertilizer, and therefore minimizes subsequent nitrite / nitrate leaching and / or ammonia volatilization. In addition, the presence of polymers in the formulation enhances the availability of nutrients to plants. Therefore, the amount of nitrogen fertilizer used with the formulation disclosed herein is at least 60% less than the recommended amount.

[0270] [Table 8]

Claims

1. comprising a nitrogen-stabilizing composition and a vehicle, The nitrogen-stabilizing composition is A nitrogen stabilizer component wherein the nitrogen stabilizer component is a urease inhibitor and / or nitrification inhibitor, and An organic acid anhydride component comprising an organic acid anhydride polymer, wherein the organic acid anhydride polymer is a copolymer containing at least two different repeating units, each containing one type B repeating unit and one type C repeating unit, wherein the type B repeating unit is derived from an (un)substituted monomer of maleic anhydride, an (un)substituted monomer of itaconic anhydride, or a combination thereof, and the type C repeating unit is derived from a substituted alkene, an unsubstituted alkene, or a combination thereof, The aforementioned vehicle is, aprotic solvents, and Contains amine stabilizers, Stabilized formulation.

2. The stabilizing formulation according to claim 1, wherein the nitrogen stabilizer component is N-(n-butyl)thiophosphate triamide (NBPT) and / or dicyanamide (DCD).

3. The stabilized formulation according to claim 1, wherein the type B repeating unit is derived from a substituted monomer of maleic anhydride, an unsubstituted monomer of maleic anhydride, or a combination thereof.

4. The stabilized formulation according to claim 1, wherein at least 50 mol% of the repeating units of the organic acid anhydride polymer are type B repeating units.

5. The stabilized formulation according to claim 3, wherein the alkene is selected from ethylene, propylene, butylene, isobutylene, styrene, methyl vinyl ether, and combinations thereof.

6. The aforementioned organic acid anhydride polymer has the structure of the following formula, 【Chemistry 1】 In the formula, R １ , R ２ , R ３ , and R ４ However, independently selected from -H, -OR, -alkyl, or -aryl, where R is substituted or unsubstituted C １ -C ８ It is an alkyl group, The stabilized formulation according to claim 1, wherein n is an integer greater than 2.

7. The stabilized formulation according to claim 1, wherein the aprotic solvent is selected from dichloromethane, dimethylacetamide, dimethylformamide, dimethyl sulfoxide (DMSO), ethyl acetate, acetone, acetonitrile, hexamethylphosphoramide, dimethyl sulfone, sulfolane, 1,3-dimethyl-2-imidazoidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, methyl acetate, ethyl lactate, N-methylpyrrolidone, tetrahydrofuran, and propylene carbonate.

8. The stabilizing formulation according to claim 1, wherein the amine stabilizer is selected from 1,2-diaminocyclohexane (DCH), bis(hexamethylene)triamine (BHT), monoethanolamine, ethylaminoethanol, dimethylaminoethanol, isopropylaminoethanol, diethanolamine, triethanolamine, methylaminoethanol, aminopropanol, methylaminopropanol, dimethylaminopropanol, aminobutanol, dimethylaminobutanol, aminobutanediol, trihydroxymethylaminoethane, diethylaminopropanediol, 1-amino-cyclopentanemethanol, and aminobenzyl alcohol.

9. The stabilized preparation according to claim 1, wherein the nitrogen stabilizing composition is present in an amount of 5% to 50% w / w based on the total weight of the stabilized preparation, the aprotic solvent is present in an amount of 50% to 75% w / w based on the total weight of the stabilized preparation, and the amine stabilizer is present in an amount of 3% to 8% w / w based on the total weight of the stabilized preparation.

10. The stabilized preparation according to claim 9, wherein the nitrogen stabilizer component is present in an amount of 5% to 50% w / w based on the total weight of the stabilized preparation.

11. The stabilized preparation according to claim 1, wherein the nitrogen stabilizer component comprises a urease inhibitor present in an amount of 5% to 15% w / w based on the total weight of the stabilized preparation, and a nitrification inhibitor present in an amount of 5% to 20% w / w based on the total weight of the stabilized preparation.

12. The stabilized preparation according to claim 1, wherein the nitrogen stabilizer component comprises a urease inhibitor present in an amount of 5% to 15% w / w, a nitrification inhibitor present in an amount of 5% to 20% w / w, an aprotic solvent present in an amount of 50% to 75%, and an amine stabilizer present in an amount of 3% to 8% w / w, and the total weight of all components is based on the total weight of the stabilized preparation.

13. The stabilized formulation according to claim 11, wherein the urease inhibitor is DCD, the nitrification inhibitor is NBPT, the aprotic solvent is DMSO, and the amine stabilizer is monoethanolamine.

14. An agricultural composition comprising the stabilizing agent and fertilizer described in claim 1.

15. The agricultural composition according to claim 14, wherein the fertilizer is a urea-containing fertilizer.

16. The agricultural composition according to claim 15, wherein the stabilizing agent is applied to the surface of the fertilizer in the form of an aqueous dispersion.

17. A method for inhibiting soil-derived urease enzymes, comprising the step of applying the stabilized formulation described in claim 1 to soil, wherein the formulation is present in an amount sufficient to inhibit the decomposition of urea by the action of the soil-derived urease enzymes.

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