Chlorpyrifos composition for improving nitrogen nutrient use efficiency and improving plant growth

Abstract

The subject matter of the present disclosure relates to chlorpyrifos compounds and mixtures and the synthesis of the chlorpyrifos compounds and mixtures, which are particularly suitable for agricultural use. For example, these compounds or mixtures can be applied directly to the soil, or can be applied in combination with fertilizers to increase nutrient absorption and inhibit nitrification and urease hydrolysis. More specifically, the subject matter relates to chlorpyrifos compounded or mixed with monoacids that can be further functionalized. Other uses of the chlorpyrifos compounds and mixtures and compositions containing the chlorpyrifos compounds and mixtures are disclosed.

Description

Technical Field

[0001] The presently disclosed subject matter relates to complexes and mixtures of nitrapyrin with monoacids selected from monocarboxylic acids, monosulfonic acids, and monophosphonic acids, and the synthesis of the complexes and mixtures, which are particularly useful for increasing nutrient absorption and inhibiting nitrification in agricultural applications. Background Art

[0002] Nitrogen fertilizer added to the soil is easily converted by many biological and chemical processes (including nitrification, leaching and evaporation). Many conversion processes are undesirable because they reduce the nitrogen level that the target plant can absorb. The reduction of available nitrogen requires the addition of more nitrogen-rich fertilizers to compensate for the loss of agricultural active nitrogen available to plants. Nitrification is the process in which some widespread soil bacteria metabolize the nitrogen in the form of ammonium in the soil, thereby converting nitrogen into nitrite and nitrate forms, which are more likely to lose nitrogen by leaching or by volatilization through denitrification. These problems require improved management of nitrogen to improve economic efficiency and protect the environment.

[0003] Compounds that increase the efficiency of nitrogen nutrient use attempt to reduce nitrification. These so-called nitrification inhibitors have been developed to inhibit nitrogen losses due to nitrification. As taught by Goring in US 3,135,594 (incorporated herein by reference in its entirety), one class of nitrification inhibitors used consists of various chlorinated compounds related to pyridine. Chlorpyrifos is an example of a nitrification inhibitor.

[0004] Current formulations consist of chlorpyrifos dissolved in large amounts of volatile, flammable, toxicologically problematic, environmentally problematic, and / or highly odoriferous aromatic solvents (e.g., toluene, xylene, etc.). For every unit weight of chlorpyrifos delivered to the field, more than 3-4 unit weights of such solvents are also delivered to the same soil. The relatively low concentration of active ingredient results in increased transportation costs, increased handling difficulties, and reduced efficiency. In addition, once chlorpyrifos is employed, it is lost in large amounts to the atmosphere, resulting in undesirable environmental impacts, loss of product efficacy due to loss of potency, and an unpleasant odor.

[0005] It would be desirable to find a method of inhibiting the volatilization of chlorpyrifos without employing expensive technology. Further, it would be desirable to replace existing products with formulations that are more economical, less toxic, and less harmful to the environment. Summary of the invention

[0006] In one aspect, the subject matter described herein relates to complexes or mixtures of chlorpyrifos and monoacids, and various uses of the complexes or mixtures of chlorpyrifos alone or in combination with other compounds. The monoacid can be a monocarboxylic acid, a monosulfonic acid, or a monophosphonic acid. In some embodiments, the monoacid is substituted with an alkyl, alkenyl, or aromatic ring system.

[0007] In one aspect, the subject matter described herein is directed to a composition comprising an agricultural product and chlorpyrifos complexed or mixed with a monoacid.

[0008] In one aspect, the subject matter described herein is directed to a composition comprising chlorpyrifos complexed or mixed with a monoacid and an organic solvent, wherein the concentration of chlorpyrifos is greater than about 20% wt / wt.

[0009] In some embodiments, the disclosed chlorpyrifos complexes or mixtures exhibit reduced volatility in an appropriate solvent when compared to chlorpyrifos dissolved in a solvent alone or when compared to known commercially available chlorpyrifos formulations.

[0010] In some embodiments, the subject matter described herein relates to formulations suitable for use in agriculture, wherein the formulations include the described chlorpyrifos-monoacid complexes or mixtures.

[0011] In some embodiments, the subject matter described herein relates to methods of increasing the growth, yield, and health of a plant by contacting the plant or soil in an area of ​​the plant with a composition comprising the described chlorpyrifos-monoacid complex or mixture.

[0012]

[00136] In some embodiments, the subject matter described herein relates to methods of reducing nitrification and / or reducing atmospheric ammonia.

[0013] In some embodiments, the subject matter described herein relates to methods of making the disclosed chloramphenicol-monoacid complexes or mixtures, and compositions and formulations containing the chloramphenicol-monoacid complexes or mixtures.

[0014] These and other aspects are fully described below. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 Five samples containing dissolved Image of vials of chlorpyrifos with and without monoacid in Polarclean. The contents and physical properties of the vials are as follows: Vial 1 chlorpyrifos, colorless; Vial 2 chlorpyrifos and 2,5-dihydroxybenzoic acid, light yellow in color; Vial 3 chlorpyrifos and 2,4-dihydroxybenzoic acid, yellow / orange in color; and Vial 4 chlorpyrifos and 3,4-dihydroxybenzoic acid, green / grey in color.

[0016] Figure 2 Three samples containing dissolved Image of vials of chlorpyrifos with and without monoacid in Polarclean. The contents and physical properties of the vials are as follows: Vial 1 chlorpyrifos, colorless; Vial 2 chlorpyrifos and methanesulfonic acid, colorless; and Vial 3 chlorpyrifos and 2,4-dihydroxybenzoic acid, yellow / orange in color. DETAILED DESCRIPTION

[0017] The currently disclosed subject matter will now be described more fully below. However, benefiting from the teaching presented in the foregoing description, the technical personnel in the field to which the currently disclosed subject matter is related will think of many modifications and other embodiments of the currently disclosed subject matter set forth herein. Therefore, it should be understood that the subject matter of the present disclosure is not limited to the disclosed specific embodiments, and modifications and other embodiments are intended to be included in the scope of the appended claims. In other words, the subject matter described herein covers all substitutions, modifications and equivalent forms. If one or more of the combined documents, patents and similar materials are different from or contradictory to the present application, including but not limited to defined terms, term usage, described technology, etc., the present application shall prevail. Unless otherwise defined, all technical terms and scientific terms used herein have the same meaning as those of ordinary skill in the art are generally understood. All publications, patent applications, patents and other references mentioned herein are incorporated by reference in their entirety.

[0018] Advantageously, the compositions and methods described herein have been shown to provide desirable properties for the use of chlorpyrifos in agriculture by formulating a complex or mixture of chlorpyrifos with a monoacid selected from substituted / unsubstituted monocarboxylic acids, substituted / unsubstituted monosulfonic acids, and substituted / unsubstituted monophosphonic acids. The substituted monoacids may contain alkyl, alkenyl, or aromatic ring systems. The desirable properties of such acids include, but are not limited to: low cost, higher active ingredient content relative to commercially available products, ease of preparation, excellent environmental and toxicological characteristics, and non-liquid formulations. As disclosed herein, among other properties, chlorpyrifos-monoacid complexes / mixtures have significantly lower vapor pressures, thereby reducing volatilization; increased solubility, thereby providing compositions with high loads and / or concentrations; and increased stability when formulated in an environment with reduced moisture content.

[0019] To date, methods found in the art for reducing the volatility of materials involving pyridine derivatives involve the opposite approach. For example, the use of poly(4-vinylpyridine) sulfur trioxide complexes is known in the art of sulfonation chemistry, where the volatility of sulfur trioxide is controlled by forming a complex with poly(4-vinylpyridine). In this example, the pyridine derivative portion of the molecule is the non-volatile portion, while sulfur trioxide is the volatile portion. In contrast, a significantly different approach as described herein utilizes a chlorpyrifos-monoacid complex having as a non-volatile component one or more monoacids selected from monocarboxylic acids, monosulfonic acids, and monophosphonic acids and as a volatile component a pyridine derivative such as chlorpyrifos.

[0020] I. Definitions

[0021] As used herein, the term "complex" or "complex material" refers to chelates, coordination complexes, charge transfer complexes and salts of chlorpyrifos, wherein chlorpyrifos is associated with an acidic functional group (e.g., -COOH, -SO3H, -PO3H2) of a monoacid in a covalent (i.e., bonding) or non-covalent (i.e., ionic) manner. In some cases, chlorpyrifos is associated with the entire molecule. In the complex, a central part or ion (e.g., chlorpyrifos) is associated with a surrounding array of binding molecules or ions (e.g., monoacids) called ligands or complexing agents. The central part is combined or associated with several donor atoms of a ligand, wherein each donor atom is a different atom, but an atom of the same type (e.g., oxygen (O)). A ligand or complexing agent that is combined with a central part to form multiple bonds (i.e., 2, 3, 4 or even 6 bonds) by several donor atoms in the donor atom of a ligand is called a multidentate ligand. A complex with a multidentate ligand is called a chelate. Typically, the complex of the core and the ligand is more soluble than the core itself because the ligand surrounding the core does not dissociate from the core when in solution and solvates the core, thereby increasing its solubility.

[0022] As used herein, the term "salt" refers to a compound composed of an assembly of cations and anions. Salts are composed of relevant numbers of cations (positively charged ions) and anions (negative ions) so that the product is electrically neutral (has no net charge). Many ionic compounds exhibit considerable solubility in protic solvents such as water or other polar solvents. Solubility depends on the degree to which each ion interacts with the solvent.

[0023] As used herein, the term "charge transfer complex (CT complex)" or "electron-donor-acceptor complex" is an association of two or more molecules or different parts of a macromolecule in which a small portion of the charge is transferred between the molecular entities. The resulting electrostatic attraction provides a stabilizing force for the molecular complex. The source molecule that transfers the charge is called the electron donor, and the receiving species is called the electron acceptor. The attractive forces in the charge transfer complex are not stable chemical bonds in nature, and are therefore much weaker than covalent forces.

[0024] As used herein, the term "monoacid" refers to compounds and / or ligands having a single acid functionality such as carboxylic acid (-COOH), phosphonic acid (-PO3H2 or -PO(OR2)) and / or sulfonic acid (-SO3H) that is covalently or non-covalently associated with chlorpyrifos. The monoacid can be further functionalized to contain additional functional groups (e.g., hydroxyl, cycloalkyl, amino, monosubstituted amino, disubstituted amino, acyloxy, nitro, cyano, carboxyl, alkoxycarbonyl, alkylformamide, substituted alkylformamide, dialkylformamide, substituted dialkylformamide, alkylsulfonyl, alkylsulfinyl, thioalkyl, thiohaloalkyl, alkoxy, substituted alkoxy or haloalkoxy), or even additional acid functional groups (e.g., -COOH, SO3H or PO3H2). These additional functional groups are not covalently or non-covalently associated with chlorpyrifos. Monoacids that are further functionalized may also be referred to as "polyfunctional" monoacids.

[0025] As used herein, the term "aromatic ring system" refers to a ring system containing at least one heteroaryl ring and / or at least one aryl ring.

[0026] As used herein, the term "heteroaryl" refers to a group including at least one five-membered or six-membered unsaturated and conjugated aromatic ring containing at least two ring carbon atoms and 1 to 4 ring heteroatoms selected from nitrogen, oxygen and / or sulfur. Such heteroaryl groups are often alternatively referred to as "heteroaromatic" groups by those skilled in the art. Heteroaryl groups can have two to twelve carbon atoms or alternatively 4 to 5 carbon atoms in the heteroaryl ring. Examples include but are not limited to pyridyl, pyrimidyl, pyrazinyl, pyrrolyl, furyl, tetrazolyl, isoxazolyl, oxadiazolyl, benzothienyl, benzofuranyl, quinolyl, isoquinolyl, etc.

[0027] As used herein, the term "aryl" refers to a group comprising at least one unsaturated and conjugated six-membered ring similar to the six-membered ring of benzene. Aryl groups having such unsaturated and conjugated rings are also referred to as "aromatic" groups by those skilled in the art. Preferred aryl groups have 6 to 12 ring carbons. Aryl groups include, but are not limited to, aromatic groups including phenyl and naphthyl ring groups.

[0028] As used herein, the term "substituted" refers to a moiety (such as heteroaryl, aryl, alkyl and / or alkenyl) that is combined with one or more additional organic or inorganic substituent radicals. In some embodiments, the substituted moiety includes 1, 2, 3, 4 or 5 additional substituent groups or radicals. Suitable organic and inorganic substituent radicals include, but are not limited to, hydroxyl, cycloalkyl, aryl, substituted aryl, heteroaryl, heterocycle, substituted heterocycle, amino, monosubstituted amino, disubstituted amino, acyloxy, nitro, cyano, carboxyl, alkoxycarbonyl, alkylformamide, substituted alkylformamide, dialkylformamide, substituted dialkylformamide, alkylsulfonyl, alkylsulfinyl, alkylthio, alkoxy, substituted alkoxy or halogenated alkoxy radicals, wherein the terms are defined herein. Unless otherwise specified herein, the organic substituent may include 1 to 4 or 5 to 8 carbon atoms. When more than one substituent radical is bonded to a substituted moiety, the substituent radicals may be the same or different.

[0029] As used herein, the term "unsubstituted" refers to a moiety that is not bonded to one or more additional organic or inorganic substituent radicals as described above (e.g., heteroaryl, aryl, alkenyl and / or alkyl), meaning that the moiety is substituted only with hydrogen.

[0030] As used herein, the term "halo," "halogen," or "halide" refers to a fluorine, chlorine, bromine, or iodine atom or ion.

[0031] As used herein, the term "alkoxy" refers to an alkyl radical bonded through a single terminal ether bond; that is, an "alkoxy" group can be defined as -OR, wherein R is an alkyl radical as defined above. Examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, isobutoxy, sec-butoxy, and the like.

[0032] As used herein, the term "substituted alkoxy" refers to an alkoxy radical as defined above having one, two or more additional organic or inorganic substituents bonded to the alkyl radical. Suitable organic and inorganic substituents include, but are not limited to, hydroxyl, cycloalkyl, amino, monosubstituted amino, disubstituted amino, acyloxy, nitro, cyano, carboxyl, alkoxy, alkylformamide, substituted alkylformamide, dialkylformamide, substituted dialkylformamide, alkylsulfonyl, alkylsulfinyl, thioalkyl, thiohaloalkyl, alkoxy, substituted alkoxy or halogenated alkoxy. When more than one substituent radical is bonded to the alkyl group of the alkoxy, the substituent radicals may be the same or different.

[0033] As used herein, the term "amino" refers to a substituted or unsubstituted trivalent nitrogen-containing radical or group structurally related to ammonia (NH3) by substitution of one or more hydrogen atoms of ammonia.

[0034] As used herein, the term "monosubstituted amino" refers to an amino group substituted with one radical selected from alkyl, substituted alkyl, or aralkyl, wherein the terms have the same definitions as found herein.

[0035] As used herein, the term "disubstituted amino" refers to an amino group substituted with two radicals selected from aryl, substituted aryl, alkyl, substituted alkyl or aralkyl, which may be the same or different, wherein the terms have the same definitions as disclosed herein. Examples include, but are not limited to, dimethylamino, methylethylamino, diethylamino, and the like. The two substituent radicals present may be the same or different.

[0036] As used herein, the term "haloalkyl" refers to an alkyl radical as defined above substituted with one or more halogens such as fluorine, chlorine, bromine or iodine, preferably fluorine. Examples include but are not limited to trifluoromethyl, pentafluoroethyl, etc.

[0037] As used herein, the term "haloalkoxy" refers to a haloalkyl group as defined above directly bonded to an oxygen to form a trifluoromethoxy, pentafluoroethoxy, and the like.

[0038] As used herein, the term "acyl" refers to a radical containing a carbonyl group (-C(O)-R group), wherein the R group is hydrogen or has 1 to 8 carbons. Examples include, but are not limited to, formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, hexanoyl, heptanoyl, benzoyl, and the like.

[0039] As used herein, the term "acyloxy" refers to a radical containing a carboxyl (-OC(O)-R) group, wherein the R group includes hydrogen or 1 to 8 carbons. Examples include, but are not limited to, acetoxy, propionyloxy, butyryloxy, isobutyryloxy, benzoyloxy, and the like.

[0040] As used herein, the term "alkyl" refers to a saturated hydrocarbon radical containing 1 to 8, 1 to 6, 1 to 4 or 5 to 8 carbons. Alkyl is structurally similar to non-cyclic alkane compounds modified by removing a hydrogen from non-cyclic alkanes and replacing it with a non-hydrogen group or a free radical. The alkyl radical can be branched or unbranched. The low alkyl radical has 1 to 4 carbon atoms. The high alkyl radical has 5 to 8 carbon atoms. The example of alkyl radical, low alkyl radical and high alkyl radical includes but is not limited to free radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, tert-amyl, n-pentyl, n-hexyl, isooctyl.

[0041] As used herein, the term "alkenyl" refers to an unsaturated hydrocarbon radical containing 1 to 8, 1 to 6, 1 to 4 or 5 to 8 carbons and at least one carbon-carbon double bond. Unsaturated hydrocarbon radicals are similar to alkyl radicals as defined above, and they also include 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-hexyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-hexyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, etc. The term "alkenyl" includes straight and branched dienes and trienes.

[0042] As used herein, the term "sulfuric acid" is understood to be an inorganic acid composed of elemental sulfur, oxygen and hydrogen and having the molecular formula H2SO4. Sulfuric acid is a member of the sulfonic acids.

[0043] As used herein, the term "sulfonic acid" refers to a member of the class of organic sulfur compounds having the general formula RS(=O)2-OH, where R is hydrogen, an alkyl, an alkenyl, or an aromatic ring system.

[0044] As used herein, the term "phosphoric acid," also known as orthophosphoric acid or phosphoric (V) acid, refers to an acid having the chemical formula H3PO4. Phosphoric acid is a member of the phosphonic acids.

[0045] As used herein, the term "phosphonic acid" refers to a member of the class of organophosphorus compounds containing a group of the general formula R1-PO(OH)2 or R1-PO(OR2)2, wherein R1 is hydrogen, an alkyl, an alkenyl, a hydroxyl or an aromatic system and R2 is H, an alkyl, an alkenyl or an aromatic system.

[0046] As used herein, the term "carboxylic acid" refers to a member of the class of compounds having the general formula R-COOH, where R is hydrogen, an alkyl, an alkenyl, or an aromatic system.

[0047] As used herein, the prefix "mono" is understood to mean "single" or "one". For example, the term "monocarboxylic acid" is understood to refer to a compound containing only a single carboxylic acid that associates with a chlorpyrifos molecule. The monocarboxylic acid may optionally contain a second carboxylic acid group (-COOH group), however, this second carboxylic acid group does not associate with the chlorpyrifos molecule. The same understanding also applies to terms such as "monosulfonic acid" and "monophosphonic acid".

[0048] As used herein, the term "soil" is understood to be a natural body composed of living matter (e.g., microorganisms (such as bacteria and fungi), animals and plants) and non-living matter (e.g., minerals and organic matter (e.g., organic compounds in varying degrees of decomposition), liquids and gases) present on the surface of the earth and characterized by soil layers that differ from the initial material due to various physical, chemical, biological and anthropogenic processes. From an agricultural point of view, soil is primarily viewed as an anchor and macronutrient base for plants (plant habitat).

[0049] As used herein, the term "fertilizer" is understood to be a compound for promoting plant and fruit growth. Fertilizer is usually applied through soil (for absorption by plant roots) or foliar fertilization (for absorption by leaves). The term "fertilizer" can be subdivided into two major categories: a) organic fertilizer (consisting of rotten plant / animal matter) and b) inorganic fertilizer (consisting of chemicals and minerals). Organic fertilizers include manure, mud, worm fallout, peat, seaweed, sewage and guano. Green manure crops are also regularly planted to add nutrients (especially nitrogen) to the soil. The organic fertilizer manufactured includes compost, blood meal, bone meal and seaweed extract. Other examples are enzyme-digested protein, fish meal and feather meal. Crop residues decomposed in previous years are another source of fertility. In addition, naturally occurring minerals, such as rock phosphates, potassium sulfate and limestone are also considered to be inorganic fertilizers. Inorganic fertilizers are usually manufactured by chemical processes (such as the Haber-Bosch process), and also use naturally occurring deposits while chemically modifying them (for example, concentrated triple superphosphate). Naturally occurring inorganic fertilizers include Chilean sodium nitrate, rock phosphates, and limestone.

[0050] As used herein, the term "manure" is an organic substance used as organic fertilizer in agriculture. Manure can be divided into liquid manure, semi-liquid manure, stable or solid manure and straw manure according to its structure. According to its source, manure can be divided into manure derived from animals or plants. Common forms of animal feces include feces, urine, farm mud (liquid manure) or farmyard manure (FYM), and FYM also contains a certain amount of plant materials (usually straw) that may have been used as bedding for animals. The animal from which manure can be used includes horses, cattle, pigs, sheep, chickens, turkeys, rabbits and guano from seabirds and bats. When used as fertilizer, the application rate of animal manure depends on source (animal type) to a great extent. Plant manure can be derived from any kind of plant, and plants can also be clearly planted for farming (for example, leguminous plants), thereby improving the structure and fertility of soil. In addition, the plant matter used as manure can include the contents of the rumen of the ruminant slaughtered, used hops (left by brewing beer) or seaweed.

[0051] As used herein, the term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, seedlings and similar forms. The seeds used can be seeds of the above-mentioned useful plants, also can be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0052] As used herein, the term "reduced volatility" and the like refers to the volatility of a chlorpyrifos-monoacid mixture or complex compared to the volatility of chlorpyrifos free base. The reduction in volatility can be quantified as described elsewhere herein.

[0053] As used herein, the term "organic solvent" refers to a non-aqueous solvent that solvates the chlorpyrifos-monoacid complex to the extent described elsewhere herein.

[0054] As used herein, the term "non-aqueous" refers to a solvent having a water content of less than 0.2 wt % based on the total weight of the solvent.

[0055] As used herein, the term "inhibiting urease" and the like refers to inhibiting the activity of urease. Inhibition can be quantified as described elsewhere herein.

[0056] As used herein, the term "nitrification inhibitor" refers to the property of compounds such as chlorpyrifos that inhibit the oxidation of ammonia to nitrite / nitrate.

[0057] Throughout the specification and claims, unless the context requires otherwise, the words "comprise," "comprises," and "comprising" are used in a non-exclusive sense, and are synonymous with "comprising," "containing," or "characterized by," meaning that it is open-ended and does not exclude additional, unrecited elements or method steps.

[0058] As used herein, the transition phrase "consisting essentially of" limits the scope of a claim to the specified materials or steps, and those materials or steps that do not materially affect the basic and novel characteristics of the claimed invention.

[0059] As used herein, the transitional phrase "consisting of" excludes any elements, steps, or ingredients not specified in a claim.

[0060] Another definition may be as follows.

[0061] II. Composition

[0062] Compounds or mixtures of chlorpyrifos and monoacids selected from monocarboxylic acids, monosulfonic acids and monophosphonic acids have been prepared. In certain embodiments, the monophosphonic acid is not phosphoric acid (i.e., chlorpyrifos is not compounded or mixed with phosphoric acid). In certain embodiments, the monoacid is substituted. In such embodiments, chlorpyrifos is compounded or mixed with substituted monocarboxylic acids, monosulfonic acids, monophosphonic acids and / or any combination thereof. As described above, these compounds and mixtures can exhibit desired properties, such as significantly reduced vapor pressure, higher loads and increased chemical stability, all of which generally contribute to improved performance in the field.

[0063] The amount of chlorpyrifos and the monoacid present in the composite / mixture can vary. In some embodiments, chlorpyrifos and the monoacid are present in a weight ratio of about 1000:1 to about 1:1000, about 750:1 to about 1:750, about 1:500 to about 500:1, about 1:250 to about 250:1, about 1:100 to about 100:1, about 75:1 to about 1:75, about 1:50 to about 50:1, about 1:25 to about 25:1, about 1:20 to about 20:1, about 1:15 to about 15:1, about 1:10 to about 10:1, about 1:5 to about 5:1, about 1:3 to about 3:1, about 1:2.5 to about 2.5:1, about 1:2 to about 2:1, or about 1:1.

[0064] Generally, chlorpyrifos-monoacid complex / mixture can be used alone in composition, or composition can comprise organic solvent and other ingredients to form useful composition.In certain embodiments, described composition and formulation comprise relatively less water or do not contain water.Formulation containing a large amount of water shows the rapid degradation of chlorpyrifos, therefore chlorpyrifos should be minimized to be exposed to excessive water.In certain embodiments, by the gross weight of composition, the amount of water present in pure chlorpyrifos-monoacid complex or mixture or its formulation containing organic solvent is less than 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 or less than 0.5%w / w. In such compositions, the chemical stability of the nitrapyrin complex / mixture is at least about 50%, about 60%, about 70%, about 80%, about 85%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99%, or at least about 99.5%. See, e.g., Meikle et al., "The hydrolysis and photolysis rates of nitrapyrin in dilute aqueous solution," Arch. Environm. Contain. Toxicol., 7, 149-158 (1978).

[0065] In some embodiments, the compounding of chlorpyrifos as disclosed herein with a monoacid can be characterized by the color change of the compounded chlorpyrifos. For example, chlorpyrifos itself is a colorless crystalline white solid and is a transparent solution when dissolved in an organic solvent. However, when compounded with a monoacid, particularly in the presence of an organic solvent, a color change of chlorpyrifos can be observed. The color of the resulting chlorpyrifos-monoacid complex and any solution thereof with an organic solvent can vary according to the amount of chlorpyrifos and / or monoacid and / or solvent present and the functionality of the monoacid and / or solvent. In some embodiments, a color change of chlorpyrifos is not observed in the presence of a monoacid. Without being bound by theory, it is believed that in such cases, chlorpyrifos may not be compounded with a monoacid, but rather forms a chlorpyrifos-monoacid mixture. Surprisingly, these chlorpyrifos-monoacid mixtures can also exhibit substantially the same beneficial properties as the chlorpyrifos-monoacid complex.

[0066] A. Complexes and mixtures of chlorpyrifos and monobasic acids

[0067] Chlorpyrifos is a nitrification inhibitor with the following structure:

[0068]

[0069] It acts by inhibiting nitrification in the soil bacteria Nitrosomonas, which acts on ammonia by oxidizing ammonium ions to nitrites and / or nitrates. Thus, nitrification inhibition reduces nitrogen emissions from the soil.

[0070] The mixture and complex of chlorpyrifos includes those formed with suitable non-volatile monoacids. The monoacid is selected from monocarboxylic acids, monosulfonic acids and / or monophosphonic acids. In some embodiments, the monophosphonic acid is not phosphoric acid. In some embodiments, the monoacid is substituted. In some embodiments, the monoacid is selected from monocarboxylic acids (substituted or unsubstituted), monosulfonic acids, monophosphonic acids and combinations thereof. In some embodiments, chlorpyrifos is mixed or compounded with a monoacid containing an aromatic ring system. In some embodiments, chlorpyrifos is compounded or mixed with a monoacid as a monocarboxylic acid. For example, formic acid. In some embodiments, the monocarboxylic acid is substituted with an alkyl, alkenyl or aromatic ring system. Exemplary alkyl monocarboxylic acids include but are not limited to acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, octanoic acid, nonanoic acid and decanoic acid. Exemplary alkenyl monocarboxylic acids include but are not limited to acrylic acid, 3-butenoic acid, 4-pentenoic acid, 5-hexenoic acid, 6-heptenoic acid, 7-octenoic acid, 8-nonenoic acid and 9-decenoic acid. Exemplary aromatic ring system monocarboxylic acids include, but are not limited to, (un)substituted benzoic acid, (un)substituted 4-pyridinecarboxylic acid, (un)substituted nicotinic acid, (un)substituted 5-pyrimidinecarboxylic acid, (un)substituted 2-pyrazinecarboxylic acid, (un)substituted 2-quinoxalinecarboxylic acid, and (un)substituted 2-naphthalenecarboxylic acid.

[0071] In certain embodiments, chlorpyrifos is compounded or mixed with a monoacid as a monosulfonic acid. In certain embodiments, a monosulfonic acid is substituted by an alkyl, alkenyl or aromatic ring system. Exemplary alkyl monosulfonic acids include but are not limited to methanesulfonic acid, ethanesulfonic acid (e.g., 2-hydroxy-ethanesulfonic acid), 1-propanesulfonic acid (e.g., ligninsulfonic acid), 1-butanesulfonic acid, 1-propanesulfonic acid, 1-hexanesulfonic acid, 1-heptanesulfonic acid, 1-octanesulfonic acid, 1-nonanesulfonic acid and 1-decanesulfonic acid. Exemplary alkenyl monosulfonic acids include but are not limited to vinylsulfonic acid, allylsulfonic acid, 3-butene-1-sulfonic acid, 4-pentene-1-sulfonic acid, 5-hexene-1-sulfonic acid, 6-heptene-1-sulfonic acid, 7-octene-1-sulfonic acid, 8-nonene-1-sulfonic acid and 9-decene-1-sulfonic acid. Exemplary aromatic ring system monosulfonic acids include, but are not limited to, (un)substituted benzenesulfonic acids (e.g., cumenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid), (un)substituted 4-pyridinesulfonic acid, (un)substituted 3-pyridinesulfonic acid, (un)substituted 5-pyrimidinesulfonic acid, (un)substituted 2-pyridinesulfonic acid, (un)substituted 2-quinoxalinesulfonic acid, and (un)substituted 2-naphthalenesulfonic acid.

[0072] In certain embodiments, chlorpyrifos is compounded or mixed with a monoacid as a monophosphonic acid. In certain embodiments, the monophosphonic acid is not phosphoric acid. In certain embodiments, the monophosphonic acid is substituted by an alkyl, alkenyl or aromatic ring system. Exemplary alkyl monophosphonic acids include but are not limited to methylphosphonic acid, ethylphosphonic acid, propylphosphonic acid, butylphosphonic acid, pentylphosphonic acid, hexylphosphonic acid, heptylphosphonic acid, octylphosphonic acid, nonylphosphonic acid and decylphosphonic acid. Exemplary alkenyl monophosphonic acids include but are not limited to vinylphosphonic acid, allylphosphonic acid, 3-butene-1-phosphonic acid, 4-pentene-1-phosphonic acid, 5-hexene-1-phosphonic acid, 6-heptene-1-phosphonic acid, 7-octene-1-phosphonic acid, 8-nonene-1-phosphonic acid and 9-decene-1-phosphonic acid. Exemplary aromatic ring system monophosphonic acids include, but are not limited to, (un)substituted benzenephosphonic acid, (un)substituted 4-pyridinephosphonic acid, (un)substituted 3-pyridinephosphonic acid, (un)substituted 5-pyrimidinephosphonic acid, (un)substituted 2-pyridinephosphonic acid, (un)substituted 2-quinoxalinephosphonic acid, and (un)substituted 2-naphthylphosphonic acid.

[0073] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted with one or more of the following: -OR1, -C(=O)R2, -PO3H, -PO3R4, -SO3H, -SO3R4, -N(R3)(R4), -C1-C6 alkyl, halogen, -CN, -CF3, -NO2 and -CF3;

[0074] wherein R1 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl);

[0075] R2 is -H, -OH, -N(R4)(R4), -C1-C6 alkyl or -O(C1-C6 alkyl);

[0076] R3 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0077] R4 is -H or -C1-C6 alkyl.

[0078] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted with one or more of -OR1, -C(=O)R2 and -C1-C6 alkyl;

[0079] wherein R1 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0080] R2 is -H, -OH, -C1-C6 alkyl or -O(C1-C6 alkyl).

[0081] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted by one or more of the following: halogen, -OH, -OCH3, -C(=O)H, -COOH, -C(=O)CH3, -C(=O)OCH3, -OC(=O)CH3, -CH3, -NH2, -NHCH3, -N(CH3)2 and -NC(=O)CH3.

[0082] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted with one or more of the following: halogen, -OH, -OCH3, -C(=O)H, -COOH, -C(=O)CH3, -C(=O)OCH3, -OC(=O)CH3 and -CH3.

[0083] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted with one or more of the following: halogen, -OH, -OCH3, and -C(=O)H, -COOH.

[0084] In some embodiments, the alkyl, alkenyl or aromatic ring system of the monoacid is further substituted with one or more of -OH, -OCH3 and -COOH.

[0085] In some embodiments, the monoacid is substituted with an aromatic ring system. In some embodiments, the aromatic ring system includes one or more heteroatoms selected from N, S and O. In some embodiments, the aromatic ring system is a heteroaryl ring system. In some embodiments, the aromatic ring system is an aryl ring system. In some embodiments, the aryl ring system is a benzene ring. In some embodiments, the monoacid substituted with an aryl ring system is a monocarboxylic acid.

[0086] In some embodiments, chlorpyrifos is compounded or mixed with a monoacid, wherein the monoacid is a compound of formula (I):

[0087]

[0088] wherein X1, X2, X3, X4 and X5 are independently selected from C and N, provided that no more than three of X1, X2, X3, X4 and X5 are N, and the three Ns are not directly adjacent to each other; and Y1, Y2, Y3, Y4 and Y5 are independently selected from H, -OR1, -C(=O)R2, C1-C6 alkyl, -N(R3)(R4) and are absent,

[0089] wherein R1 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl);

[0090] R2 is -H, -OH, -N(R4)(R4), -C1-C6 alkyl or -O(C1-C6 alkyl);

[0091] R3 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0092] R4 is -H or -C1-C6 alkyl.

[0093] In some embodiments, X1, X2, X3, X4 and X5 are C. In some embodiments, Y1, Y2, Y3, Y4 and Y5 are independently selected from -H, -OH, -OCH3, -C(=O)OH, -C1-C6 alkyl and absent. In some embodiments, Y1, Y2, Y3, Y4 and Y5 are independently selected from -H and -OH.

[0094] In some embodiments, the monoacid is a dihydroxybenzoic acid. Exemplary dihydroxybenzoic acids as dihydroxybenzoic acid types include, but are not limited to, 3,5-dihydroxybenzoic acid (3,5-DHB acid), 2,4-dihydroxybenzoic acid (2,4-DHB acid), 2,6-dihydroxybenzoic acid (2,6-DHB acid), and any isomers and / or mixtures thereof. In some embodiments, the monoacid is a catechol acid. Exemplary catechol acids include, but are not limited to, 2,3-dihydroxybenzoic acid (2,3-DHB acid) and / or 3,4-dihydroxybenzoic acid (3,4-DHB acid). In some embodiments, the monoacid is hydroquinone (HQ) acid. Exemplary HQ acid is 2,5-dihydroxybenzoic acid (2,5-DHB acid).

[0095] In some embodiments, the monoacid is a monocarboxylic acid selected from 4-hydroxy-3-methoxybenzoic acid (vanillic acid), 3,4-dimethoxybenzoic acid and 2,4-dihydroxybenzoic acid (2,4-DHB acid). In some embodiments, the monoacid is a monosulfonic acid, such as methanesulfonic acid.

[0096] In some embodiments, the monoacid suitable for forming a useful complex or mixture with chlorpyrifos has one or more of the following: a lower vapor pressure than the vapor pressure of chlorpyrifos not complexed or mixed with the monoacid, and / or a lower volatility than the volatility of chlorpyrifos not complexed or mixed with the monoacid. In some embodiments, the vapor pressure of chlorpyrifos in the chlorpyrifos-monoacid complex or mixture is less than 0.5 mmHg at 20°C. In addition, the loading amount of chlorpyrifos in the formulation has been significantly increased.

[0097] In some embodiments, chlorpyrifos-monoacid complexes or mixtures can be formed with one, two or more monoacids. In some embodiments, the monoacids are different. In some embodiments, the monoacids are the same.

[0098] In some embodiments, chlorpyrifos may be present in the form of a mixture of a complex and a free form. The ratio of the complex to the free form may be 1000:1 to 0.1:1, so that the composition can reduce the volatilization loss of chlorpyrifos in the atmosphere by at least 10% compared to the same composition lacking the complex described herein (i.e., chlorpyrifos not complexed with one or more monoacids). Therefore, the composition described herein may include both the complex and the free form, as long as the volatilization loss is reduced as described elsewhere herein.

[0099] In some embodiments, the chlorpyrifos-monoacid complex can be formed in the absence of a solvent (eg, an organic solvent). In some embodiments, the chlorpyrifos-monoacid complex is formed in the presence of a solvent (eg, an organic solvent).

[0100] B. Organic solvents

[0101] In some embodiments, the solvent is an organic solvent. In some embodiments, the solvent is a polar organic solvent. In some embodiments, the polar organic solvent is EPA approved. EPA approved solvents are those approved for food and non-food uses and can be found in the electronic code of federal regulations, such as in Title 40, Chapter I, Subchapter E, Part 180. EPA approved solvents include, but are not limited to, those listed in Table 1. EPA approved solvents:

[0102]

[0103]

[0104] In certain embodiments, the organic solvent is selected from sulfone, sulfoxide, oil, aromatic solvent, halogenated solvent, diol-based solvent, fatty acid-based solvent and acetate-containing solvent, ketone-containing solvent, ether polyol-containing solvent, amide-containing solvent and combination thereof. In certain embodiments, the organic solvent is sulfone. Sulfone solvent can be but not limited to sulfolane, methyl sulfolane (3-methyl sulfolane), dimethyl sulfone and combination thereof. In certain embodiments, the organic solvent is sulfoxide. Sulfoxide solvent can be but not limited to dimethyl sulfoxide.

[0105] In some embodiments, the organic solvent is an ether polyol. The ether polyol solvent can be, but is not limited to, polyethylene glycol, polypropylene glycol, polyalkylene glycol and related compounds. In some embodiments, polyethylene glycol has two terminal alcohols. Exemplary polyethylene glycols include, but are not limited to, diethylene glycol, triethylene glycol and combinations thereof. Exemplary polypropylene glycols include, but are not limited to, dipropylene glycol, tripropylene glycol and combinations thereof. In some embodiments, polypropylene glycol has three terminal alcohols. Exemplary polypropylene glycols with three terminal alcohols, called propoxylated glycerol, include, but are not limited to, Dow PT250 (it is a glycerol ether polymer with a molecular weight of 250 containing three terminal hydroxyls) and Dow PT700 (it is a glycerol ether polymer with a molecular weight of 700 containing three terminal hydroxyls). In some embodiments, ether polyols include polyethylene or polypropylene glycol with a molecular weight range of about 200Da and about 10,000Da. In some embodiments, one or more hydroxyls present in the hydroxyls in the ether polyols are modified. For example, in some embodiments, one or more hydroxyls present in the hydroxyls in the ether polyols are alkylated and / or esterified. Exemplary modified ether polyols include, but are not limited to, triacetin, n-butyl ether of diethylene glycol, ethyl ether of diethylene glycol, methyl ether of diethylene glycol, acetate of ethyl ether of dipropylene glycol, and any combination thereof. In some embodiments, the ether polyol is a cyclic carbonate (e.g., propylene carbonate). It has been found that the chlorpyrifos-monoacid complex composition containing an ether polyol is more suitable for forming a higher solid and / or active ingredient content than the previously described composition containing an ester. In some embodiments, the ether-polyol is liquid at 20°C. In some embodiments, the ether-polyol is solid at 20°C.

[0106] In some embodiments, the organic solvent is a diol-based solvent. A diol is an alcohol containing two hydroxyl groups (-OH) connected to different carbon atoms (e.g., terminal carbon atoms). The simplest diol is ethylene glycol, but the solvent should not be limited thereto.

[0107] In some embodiments, the organic solvent is an oil. Exemplary oils include, but are not limited to, mineral oil and / or kerosene.

[0108] In some embodiments, the organic solvent is a fatty acid-based solvent. In some embodiments, the fatty acid contains 3 to about 20 carbon atoms. Examples of fatty acid-based solvents include, but are not limited to, dialkyl amides of fatty acids (e.g., dimethyl amides). Examples of dimethyl amides of fatty acids include, but are not limited to, dimethyl amides of caprylic acid, dimethyl amides of C8-C10 fatty acids ( AMD 810 (N,N-dimethyloctanamide, CAS No.: 1118-92-9 and N,N-dimethyldecanamide, CAS No.: 14433-76-2)), dimethyl amide of natural lactic acid ( AMD 3L ((N,N-dimethylacetamide; CAS No.: 35123-06-9)) and combinations thereof.

[0109] In some embodiments, the organic solvent is a ketone-containing solvent. Examples of ketone-containing solvents include, but are not limited to, isophorone, trimethylcyclohexanone, and combinations thereof.

[0110] In some embodiments, the organic solvent is an acetate-containing solvent. Examples of acetate-containing solvents include, but are not limited to, acetate, hexyl acetate, heptyl acetate, and combinations thereof.

[0111] In some embodiments, the organic solvent is an amide-containing solvent. Examples of amide-containing solvents include but are not limited to ADMA 10 (CAS No.: 14433-76-2; N, N-dimethyloctanamide), AMD 810 (CAS No.: 1118-92-9 / 14433-76-2; blend of N,N-dimethyloctanamide and N,N-dimethyldecanamide), Polarclean (CAS No.: 1174627-68-9; methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate) and combinations thereof.

[0112] In some embodiments, the organic solvent is a halogenated solvent. In some embodiments, the halogenated solvent is a halogenated aromatic hydrocarbon. An example of a halogenated aromatic hydrocarbon is chlorobenzene. In some embodiments, the halogenated solvent is a halogenated aliphatic hydrocarbon. An example of a halogenated aliphatic hydrocarbon is 1,1,1-trichloroethane.

[0113] In some embodiments, the organic solvent is an aromatic solvent. In some embodiments, the aromatic solvent is an aromatic hydrocarbon. Exemplary aromatic hydrocarbons include, but are not limited to, benzene, naphthalene, and combinations thereof. In some embodiments, the aromatic hydrocarbon is substituted. Examples of substituted aromatic hydrocarbons include, but are not limited to, alkyl-substituted benzene and / or alkyl-substituted naphthalene. Examples of alkyl-substituted benzene include xylene, toluene, propylbenzene, and combinations thereof. In some embodiments, the organic solvent includes xylene. In some embodiments, the aromatic hydrocarbon is a mixture of substituted and unsubstituted aromatic hydrocarbons, such as, but not limited to, a mixture of naphthalene and alkyl-substituted naphthalene.

[0114] In some embodiments, the aromatic solvent is a mixture of hydrocarbons. For example, in some embodiments, the aromatic solvent is: Aromatics 100, a solvent containing naphtha (CAS No.: 64742-95-6), which is a combination of hydrocarbons obtained from the distillation of an aromatic material stream consisting mainly of aromatic hydrocarbons C8 to C10; or Aromatics 200, a solvent containing a mixture of: aromatic hydrocarbons (C11-C14) present at 50-85 wt% based on the total weight of the aromatics 200 composition; naphthalene (CAS No.: 91-20-3) present at 5-20 wt%; aromatic hydrocarbons (C10) not containing naphthalene present at 5-15 wt%, and aromatic hydrocarbons (C15-C16) present at 5-15 wt%. In some embodiments, the aromatic hydrocarbon is a mixture of Aromatics 100 and Aromatics 200.

[0115] In some embodiments, the organic solvent can be, but is not limited to, an aromatic solvent (such as, but not limited to, alkyl-substituted benzene, xylene, propylbenzene, mixed naphthalene and alkylnaphthalene); mineral oil; kerosene; dialkyl amides of fatty acids (including, but not limited to, dimethyl amides of fatty acids, dimethyl amide of octanoic acid); chlorinated aliphatic and aromatic hydrocarbons (including, but not limited to, 1,1,1-trichloroethane, chlorobenzene); esters of glycol derivatives (e.g., acetates of n-butyl, ethyl or methyl ether of diethylene glycol and methyl ether of dipropylene glycol); ketone-containing solvents (e.g., including, but not limited to, isophorone and trimethylcyclohexanone (dihydroisophorone)); and acetate-containing solvents (including, but not limited to, hexyl acetate and heptyl acetate).

[0116] In some embodiments, the organic solvent may be, but is not limited to, aromatic 100 (CAS No. 64742-95-6), aromatic 200 (CAS No. 64742-94-5), sulfone, glycol-based solvent, ether polyol (e.g., dipropylene glycol, Dow PT250, Dow PT700, PT250, triethylene glycol, tripropylene glycol, propylene carbonate, triacetin), dialkyl amides of saturated monocarboxylic acid fatty acids containing 3 to 20 carbon atoms (e.g., AMD 810, AMD 3L), amide-containing solvents (e.g. ADMA 10, Polarclean and ADMA 810) or a mixture thereof.

[0117] In some embodiments, the organic solvent is relatively free of water. In some embodiments, the organic solvent contains less than 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 of water, based on the total weight of the solvent.

[0118] In some embodiments, the amount of organic solvent in the composition containing chlorpyrifos-monoacid complex or mixture can vary. In some embodiments, the amount of solvent present in the composition is about 10% w / w to about 90% w / w, about 20% w / w to about 80% w / w, about 30% w / w to about 70% w / w, about 50% w / w to about 65% w / w, about 55% w / w to about 60% w / w, about 55% w / w to about 60% w / w, or about 55% w / w to about 65% w / w, based on the total weight of the composition.

[0119] In some embodiments, the organic solvent is a liquid at 20° C. In other embodiments, the organic solvent is a solid at 20° C.

[0120] In some embodiments, a composition containing a chlorpyrifos-monoacid complex or mixture can be formulated with two different solvent types. The chlorpyrifos-monoacid complex or mixture formulated in two different solvent types can exhibit high solvation, relative lack of volatility, and suitable environmental and toxicological characteristics. The two different solvent types can be selected from two different aromatic solvents, two different amide-containing solvents, two different sulfoxides or sulfoxides and aromatic solvents, or sulfoxides and amide-containing solvents. In some embodiments, the two different solvent types are xylene and dimethyl sulfoxide (DMSO). In some embodiments, the two different solvent types are dimethyl sulfoxide (DMSO) and Polarclean. The amount of each solvent type present in the composition containing the chlorpyrifos-monoacid complex or mixture can vary. In some embodiments, the first solvent of the two different solvent types is present in an amount ranging from about 10% w / w to about 90% w / w, about 20% w / w to about 80% w / w, about 30% w / w to about 70% w / w, or about 40% w / w to about 60% w / w, based on the total weight of the composition. In some embodiments, the second solvent of the two different solvent types is present in an amount ranging from about 10% w / w to about 90% w / w, about 20% w / w to about 80% w / w, about 30% w / w to about 70% w / w, or about 40% w / w to about 60% w / w, based on the total weight of the composition. In some embodiments, the first solvent is dimethyl sulfoxide (DMSO). In some embodiments, the second solvent is xylene or Polarclean. In some embodiments, the first solvent is present in an amount of about 50% w / w, based on the total weight of the composition.

[0121] In some embodiments, the amount of the first solvent and the amount of the second solvent are present in a weight ratio of about 100:1 to about 1:100, about 75:1 to about 1:75, about 50:1 to about 1:50, about 25:1 to about 1:25, about 20:1 to about 1:20, about 15:1 to about 1:15, about 10:1 to about 1:10, about 5:1 to about 1:5, about 4:1 to about 1:4, about 3:1 to about 1:3, about 2:1 to about 1:2, or about 1:1.

[0122] In some embodiments, the solubility of chlorpyrifos in the solution / solvent at 20°C is greater than 15% w / w (chlorpyrifos compared to total weight), for example, about 15% w / w to about 22% w / w, or about 17% w / w to about 21% w / w, or greater than 16% w / w, greater than 17% w / w, greater than 18% w / w, greater than 19% w / w, greater than 20% w / w, greater than 21% w / w, greater than 22% w / w, greater than 23% w / w, greater than 24% w / w, or greater than 25% w / w, greater than 26% w / w, greater than 27% w / w, greater than 28% w / w, greater than 29% w / w, greater than 30% w / w, greater than 35% w / w, greater than 40% w / w, or greater than 45% w / w.

[0123] The solvent can be present in the composition in an amount of 0.1% w / v to about 99.9% w / v. In certain embodiments, the amount of the solvent will be minimized as the amount of chlorpyrifos-monoacid complex or mixture is maximized. In certain embodiments, the amount of the solvent is less than 80% w / v, less than 79% w / v, less than 78% w / v, less than 77% w / v, less than 76% w / v, less than 75% w / v, less than 74% w / v, less than 73% w / v, less than 72% w / v, less than 71% w / v, less than 70% w / v, less than 65% w / v, less than 60% w / v, or less than 55% w / v. In some embodiments, the amount of solvent is 55% w / v to about 98% w / v; or about 60% w / v to about 97% w / v; or about 61% w / v to about 95% w / v; or about 62% w / v to about 90% w / v; or about 63% w / v to about 85% w / v; or about 64% w / v to about 80% w / v.

[0124] The composition includes chloranil in the form of a complex or mixture. Advantageously, it has been found that a complex or mixture of chloranil with a monoacid selected from a monocarboxylic acid, a monosulfonic acid and a monophosphonic acid provides an excellent loading capacity that has not been disclosed so far. The advantages of the highly concentrated composition include lower transportation costs and easy disposal. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 1wt.% to about 50wt.%. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 10wt.% to about 50wt.%. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 20wt.% to about 50wt.%. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 25wt.% to about 50wt.%. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 30wt.% to about 50wt.%. In some embodiments, by the total weight of the composition, the composition includes chloranil in the range of about 25wt.% to about 45wt.%. In some embodiments, the composition includes chloramphenicol in the range of about 25 wt.% to about 40 wt.%, based on the total weight of the composition. In some embodiments, the composition includes chloramphenicol in the range of about 25 wt.% to about 35 wt.%, based on the total weight of the composition. In some embodiments, the composition includes chloramphenicol in the range of about 28 wt.% to about 32 wt.%, based on the total weight of the composition. In some embodiments, the composition includes chloramphenicol in the range of about 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50 wt.%, based on the total weight of the composition.

[0125] The amount of monoacid present in the complex may vary. In some embodiments, the amount of monoacid present in the chlorpyrifos-monoacid complex or mixture is about 1% w / w to about 80% w / w, about 10% w / w to about 70% w / w, about 10% w / w to about 60% w / w, about 10% w / w to about 50% w / w, about 20% w / w to about 50% w / w, about 35% w / w to about 55% w / w, about 40% w / w to about 50% w / w, about 1% w / w to about 40% w / w, about 1% w / w to about 30% w / w, about 5% w / w to about 25% w / w, about 10% w / w to about 20% w / w, about 10% w / w to about 15% w / w, or about 15% w / w to about 20% w / w, based on the total weight of the composition containing chlorpyrifos monoacid. In addition, the skilled person will also appreciate that, due to the toxicology and environmental characteristics of the monoacid selected, the monoacid selected can only be present in the composition with a certain amount. Exemplary acid includes but is not limited to 2-hydroxyethanesulfonic acid, ligninsulfonic acid, cumenesulfonic acid, toluenesulfonic acid, dimethylbenzenesulfonic acid and methanesulfonic acid. The skilled person will know what type of acid shows undesirable toxicology and environmental properties, and will adjust their amount in the composition accordingly. For example, by the gross weight of the composition, the composition disclosed herein can include an amount less than about 3%, about 2.5%, about 2.0%, about 1.5%, about 1.0%, about 0.9%, about 0.8%, about 0.7%, about 0.6%, about 0.5%, about 0.4%, about 0.3%, about 0.2%, about 0.1% or about 0.01% of the monoacid selected from 2-hydroxyethanesulfonic acid, ligninsulfonic acid, cumenesulfonic acid, toluenesulfonic acid, dimethylbenzenesulfonic acid and methanesulfonic acid.

[0126] The amount of chlorpyrifos-monoacid complex / mixture including chlorpyrifos and monoacid can vary. In certain embodiments, the composition includes pure chlorpyrifos-monoacid complex / mixture and there is no solvent (this means that by the gross weight of the composition, the amount of chlorpyrifos-monoacid complex / mixture is 100%w / w). In certain embodiments, the composition includes chlorpyrifos-monoacid complex / mixture and solvent. In such embodiments, by the gross weight of the composition, chlorpyrifos-monoacid complex / mixture exists with the amount of about 20%w / w to about 80%w / w, about 25%w / w to about 75%w / w, about 30%w / w to about 60%w / w, about 35%w / w to about 55%w / w or about 40%w / w to about 50%w / w.

[0127] In some embodiments, a composition containing a chlorpyrifos-monoacid complex / mixture is disclosed. The chlorpyrifos-monoacid complex / mixture is more easily dissolved in a suitable solvent than chlorpyrifos alone or with formulations of the prior art. The described chlorpyrifos-monoacid complex / mixture can form a solution of greater than or equal to 25% by weight of chlorpyrifos. Suitable solvents include, but are not limited to, aromatics 100 (CAS No.: 64742-95-6), aromatics 200 (CAS No.: 64742-94-5), sulfones (e.g., dimethyl sulfoxide (DMSO)), amide-containing solvents (e.g., Polarclean), aromatic solvents (e.g., xylene), and ethylene glycol. In some embodiments, the organic solvent is DMSO and xylene. In some embodiments, the solvent is DMSO and In some embodiments, the solvent is Polarclean.

[0128] In some embodiments, the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, the monoacid in an amount of about 10% w / w to about 50% w / w, and the organic solvent in an amount of about 20% w / w to about 60% w / w, based on the total weight of the composition.

[0129] In some embodiments, the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, the monoacid in an amount of about 10% w / w to about 20% w / w, and the organic solvent in an amount of about 50% w / w to about 60% w / w, based on the total weight of the composition.

[0130] In some embodiments, the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, based on the total weight of the composition; a monoacid selected from 3,4-DHB acid, 2,4-DHB acid, 2,5-DHB acid, vanillic acid, 3,4-dimethoxybenzoic acid, methanesulfonic acid, and any combination thereof present in an amount of about 10% w / w to about 50% w / w; and a monoacid selected from Organic solvents include Polarclean, DMSO, xylene and any combination thereof.

[0131] In some embodiments, the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, based on the total weight of the composition; a monoacid selected from 3,4-DHB acid, 2,4-DHB acid, 2,5-DHB acid, vanillic acid, 3,4-dimethoxybenzoic acid, methanesulfonic acid, and any combination thereof, present in an amount of about 10% w / w to about 20% w / w; and a monoacid selected from methyl sulfoxide, present in an amount of about 50% w / w to about 60% w / w. Organic solvents include Polarclean, DMSO, xylene and any combination thereof.

[0132] In some embodiments, the composition has a solids content that can vary. In some embodiments, the solids content of the composition ranges from about 10% w / w to about 50% w / w, about 20% w / w to about 50% w / w, about 30% w / w to about 50% w / w, about 35% w / w to about 50% w / w, about 40% w / w to about 50% w / w, about 35% w / w to about 45% w / w, about 40% w / w to about 45% w / w, or about 45% w / w to about 50% w / w, based on the gross weight of the composition.

[0133] In some embodiments, the chlorpyrifos complexed with a monoacid disclosed herein and the compositions comprising these complexes or mixtures reduce the volatility of chlorpyrifos by about 5% to about 40% relative to untreated chlorpyrifos (i.e., chlorpyrifos not complexed or mixed with a monoacid selected from a monocarboxylic acid, a monosulfonic acid, and a monophosphonic acid). In some embodiments, the monophosphonic acid is not phosphoric acid. In some embodiments, the chlorpyrifos complexed or mixed with a monoacid disclosed herein and the compositions comprising these complexes or mixtures reduce the volatility of chlorpyrifos by about 8% to about 35% relative to untreated chlorpyrifos. In some embodiments, the chlorpyrifos complexed or mixed with a monoacid and the compositions comprising these complexes or mixtures reduce the volatility of chlorpyrifos by about 10% to about 40%, about 10% to about 35%, about 10% to about 30%, about 15% to about 35%, about 15% to about 30%, about 20% to about 30%, or about 25% to about 35% relative to untreated chlorpyrifos. In some embodiments, chlorpyrifos complexed or mixed with a monoacid and compositions comprising these complexes or mixtures reduce the volatility of chlorpyrifos by at least about 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%, 31%, 32%, 33%, 34%, or at least about 35% compared to untreated chlorpyrifos.

[0134] In some embodiments, the composition includes chlorpyrifos and the following solvent-monoacid combinations: 4-hydroxy-3-methoxybenzoic acid (vanillic acid), 3,4-dihydroxybenzoic acid; 3,4-dimethoxybenzoic acid; 2,4-dihydroxybenzoic acid; 2,5-dihydroxybenzoic acid and / or methanesulfonic acid and xylene, dimethyl sulfoxide (DMSO) and / or One or more of Polarclean.

[0135] In some embodiments, the composition includes chlorpyrifos, solvents xylene and DMSO, and a monoacid selected from 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, vanillic acid, 3,4-dimethoxybenzoic acid, and combinations thereof.

[0136] In some embodiments, the composition comprises chlorpyrifos, a solvent DMSO and Polarclean, and a monoacid selected from the group consisting of 3,4-dihydroxybenzoic acid, vanillic acid, 3,4-dimethoxybenzoic acid, and combinations thereof.

[0137] In some embodiments, the composition comprises chlorpyrifos, a solvent Polarclean and a monoacid selected from the group consisting of 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, and combinations thereof.

[0138] III. Agricultural Compositions

[0139] Any of the described chlorpyrifos-monoacid complexes / mixtures and compositions comprising these chlorpyrifos-monoacid complexes / mixtures can be combined with one or more agricultural products to provide agricultural compositions. The agricultural product can be selected from the group consisting of: fertilizers, agriculturally active compounds, seeds, compounds having urease inhibitory activity, nitrification inhibitory activity, pesticides, herbicides, insecticides, fungicides, acaricides, etc. In some embodiments, the agricultural composition can include an organic solvent, such as those discussed above.

[0140] In some embodiments, the chlorpyrifos-monoacid complex / mixture can be mixed with a fertilizer product, applied to the fertilizer product as a surface coating, or otherwise thoroughly mixed with a fertilizer product. In some embodiments, in the fertilizer / chlorpyrifos-monoacid complex / mixture composition of this combination, the fertilizer is in the form of particles, the average diameter of the particles being about powder size (less than about 0.001 cm) to about 10 mm, more preferably about 0.1 mm to about 5 mm, and still more preferably about 0.15 mm to about 3 mm. Chlorpyrifos can be present in the product of this combination at a level of about 0.001 g to about 20 g per 100 g of fertilizer, about 0.01 g to 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 the fertilizer / chlorpyrifos-monoacid complex / mixture product of combination, the application level of the product of combination can make the amount of the chlorpyrifos-monoacid complex / mixture applied be about 10-150g per acre of soil, about 30-125g per acre or about 40-120g per acre of soil. According to the judgment of the user, the product of combination can be applied in the form of liquid dispersion or dry granular product equally. When chlorpyrifos-monoacid complex / mixture is used as coating, chlorpyrifos-monoacid complex / mixture can account for about 0.005 weight % to about 15 weight % of the fertilizer product through coating, about 0.01 weight % to about 10 weight % of the fertilizer product through coating, about 0.05 weight % to about 2 weight % of the fertilizer product through coating or about 0.5 weight % to about 1 weight % of the fertilizer product through coating.

[0141] A. Fertilizer

[0142] In certain embodiments, agricultural products are fertilizers. Fertilizer can be solid fertilizer, such as but not limited to granular fertilizer, and chlorpyrifos-monoacid complex or mixture can be applied to fertilizer in the form of liquid dispersion. Fertilizer can be in liquid form, and chlorpyrifos-monoacid complex or mixture can be mixed with liquid fertilizer. Fertilizer can be selected from the group consisting of: starting fertilizer, fertilizer based on phosphate, nitrogenous fertilizer, phosphorus fertilizer, potassium fertilizer, calcium fertilizer, magnesium fertilizer, boron fertilizer, chlorine fertilizer, zinc fertilizer, manganese fertilizer, copper fertilizer, fertilizer containing urea and ammonium nitrate and / or fertilizer containing molybdenum material. In certain embodiments, fertilizer is or contains urea and / or ammonia, including anhydrous ammonia fertilizer. In certain embodiments, fertilizer includes nitrogen, phosphorus, potassium, sulfur, calcium, magnesium or micronutrients available to plants. In certain embodiments, fertilizer is solid, particle, fluid suspension, gas or solid solution fertilizer. In certain embodiments, fertilizer includes micronutrients. Micronutrients are essential elements that plants need in small amounts. In some embodiments, the fertilizer includes metal ions selected from the group consisting of Fe, Mn, Mg, Zn, Cu, Ni, Co, Mo, V, and Ca. In some embodiments, the fertilizer includes gypsum, a member of the kieserite group, a potassium product, magnesium potassium sulfate, elemental sulfur, or magnesium potassium sulfate. Such fertilizers can be granular, liquid, gaseous, or a mixture (e.g., a suspension of solid fertilizer particles in a liquid material).

[0143] In some embodiments, the chlorpyrifos-monoacid complex / mixture is combined with any suitable liquid or dry fertilizer for application to fields and / or crops.

[0144] The described chlorpyrifos-monoacid complex / mixture or its composition can be applied together with the application of fertilizer. The chlorpyrifos-monoacid complex / mixture can be applied before, after or simultaneously with the application of fertilizer.

[0145] The fertilizer composition containing chlorpyrifos-monoacid complex / mixture can be applied in any manner that is beneficial to the crop of interest. In some embodiments, the fertilizer composition is applied to the growth medium in the form of a band or row application. In some embodiments, the composition is applied to or throughout the growth medium before sowing or transplanting the desired crop. In some embodiments, the composition can be applied to the root zone of a growing plant.

[0146] B. Seeds

[0147] In certain embodiments, agricultural seeds coated with one or more of the chlorpyrifos-monoacid complex or mixture are described. According to the gross weight of the coated seed product, the chlorpyrifos-monoacid complex or mixture can be present in the seed product at a level of about 0.001-10 wt %, about 0.004 wt %-2 wt %, about 0.01 wt % to about 1 wt % or about 0.1 wt % to about 1 wt % (or no more than 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 no more than 0.001%). Seed can be but not limited to wheat, barley, oats, triticale, rye, rice, corn, soybean, cotton or rapeseed.

[0148] C. Others

[0149] In certain embodiments, urease inhibitory compounds, nitrification inhibitory compounds, pesticides, herbicides, insecticides, fungicides and / or acaricides and described chlorpyrifos-monoacid complexes / mixtures are described. As used herein, "pesticide" refers to any agent (for example, herbicides, insecticides, fungicides) with pest control activity and is preferably selected from the group consisting of pesticides, herbicides and mixtures thereof, but does not usually include materials claiming to have plant fertilization effects, such as sodium borate and zinc compounds such as zinc oxide, zinc sulfate and zinc chloride. For the unlimited list of pesticides, see " " Farm Chemicals Handbook 2000, 2004 (Farm Chemicals Handbook 2000, 2004) " " (Meister Publishing Co, Willoughby, OH, Willoughby, Ohio), the document is hereby incorporated by reference as a whole.

[0150] Exemplary herbicides include, but are not limited to, acetochlor, alachlor, aminopyralid, atrazine, benoxacor, bromoxynil, carfentrazone, chlorsulfuron, clodinafop, clopyralid, dicamba, diclofop-methyl, dimethenamid, fenoxaprop, flucarbazone, flufenacet, flumetsulam, flumiclorac ... fluroxypyr, glufosinate-ammonium, glyphosate, halosulfuron-methyl, imazamethabenz, imazamox, imazapyr, imazaquin, imazethapyr, isoxaflutole, quinclorac, MCPA, MCP amine, MCP ester, mefenoxam, mesotrione, metolachlor, s-metolachlor, metribuzin, metsulfuron methyl), nicosulfuron, paraquat, pendimethalin, picloram, primisulfuron, propoxycarbazone, prosulfuron, pyraflufenethyl), rimsulfuron, simazine, sulfosulfuron, thifensulfuron, topramezone, tralkoxydim, triallate, triasulfuron, tribenuron, triclopyr, trifluralin, 2,4-D, 2,4-D amine, 2,4-D ester, etc.

[0151] Exemplary insecticides include, but are not limited to, 1,2-dichloropropane, 1,3-dichloropropene, abamectin, acephate, acequinocyl, acetamiprid, acethion, acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, allyxycarb, alpha cypermethrin, alpha ecdysone, amidithion, amidoflumet, aminocarb, amiton, amitraz, anabasine, arsenic trioxide, and the like. oxide), athidathion, azadirachtin, azamethiphos, azinphos ethyl, azinphos methyl, azobenzene, azocyclotin, azothoate, barium hexafluorosilicate, barthrin, benclothiaz, bendiocarb, benfuracarb, benoxafos, bensultap, benzoximate, benzyl benzoate, beta-cyfluthrin cyfluthrin), betacypermethrin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioethanomethrin, biopermethrin, bistrifluron, borax, boric acid, bromfenvinfos, bromo DDT, bromocyclen, bromophos, bromophosethyl, bromopropylate,bufencarb, buprofezin, butacarb, butathiofos, butocarboxim, butonate, butoxycarboxim, cadusafos, calcium arsenate arsenate), calcium polysulfide, camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorbenside, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlorethoxyfos, chlorfenapyr fenapyr), chlorfenethol, chlorfenson, chlorfensulphide, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate, chloroform, chloromebuform, chloromethiuron, chloropicrin, chloropropylate, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl methyl), chlorthiophos, chromafenozide, cinerin I, cinerin II, cismethrin, cloethocarb, clofentezine, closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate,coumaphos, coumithoate, crotamiton, crotoxyphos, cruentaren A, cruentaren B. crufomate, cryolite, cyanofenphos, cyanophos, cyanthoate, cyclethrin, cycloprothrin, cyenopyrafen, cyflumetofen, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin, cyromazine, cythioate, d-limonene, dazomet, DBCP, DCIP, DDT, decarbofuran, deltamethrin, demephion, demephion O, demephion S), demeton, demeton methyl, demeton O, demeton Omethyl, demeton S, demeton S methyl, demeton S methyl, demeton S sulfone methylsulphon), diafenthiuron, dialifos, diamidafos, diazinon, dicapthion, dichlofenthion, dichlofluanid, dichlorvos, dicofol, dicresyl, dicrotophos, dicyclanil, dieldrin, dienochlor, diflovidazin, diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate,dimethrin, dimethylvinphos, dimetilan, dinex, dinobuton, dinocap, dinocap 4, dinocap 6, dinocton, dinopenton, dinoprop, dinosam, dinosulfon, dinotefuran, dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion, diphenyl sulfone, disulfiram, disulfoton, dithicrofos, DNOC, dofenapyn, doramectin, ecdysterone, methylaminobutyric acid emamectin, EMPC, empenthrin, endosulfan, endothion, endrin, EPN, epofenonane, eprinomectin, esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, ethoatemethyl, ethoprophos, ethyl DDD, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, etofenprox, etoxazole, etrimfos, EXD, famphur, fenamiphos, fenazaflor, fenazaquin, fenbutatin oxide), fenchlorphos, fenethacarb, fenfluthrin, fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb, fenpirithrin, fenpropathrin, fenpyroximate, fenson,Fensulfothion, fenthion, fenthion ethyl, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, fluazuron, flubendiamide, flubenzimine, flucofuron, flucycloxuron, flucythrinate, fluenetil, flufenerim, flufenoxuron, flu fenprox), flumethrin, fluorbenside, fluvalinate, fonofos, formetanate, formothion, formparanate, fosmethilan, fospirate, fosthiazate, fosthietate, fosthietate, furathiocarb, furethrin, furfural, gamma cyhalothrin cyhalothrin), γHCH, halfenprox, halofenozide, HCH, HEOD, heptachlor, heptenophos, heterophos, hexaflumuron, hexythiazox, HHDN, hydramethylnon, hydrogen cyanide, hydroprene, hyquincarb, imiphos cyafos), imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isamidophos, isazofos, isobenzan, isocarbophos, isodrin, isofenphos, isoprocarb, isoprothiolane, isothioate,isoxathion, ivermectin jasmolin I, jasmolin II, jodfenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan, kinoprene, lambdacyhalothrin, lead arsenate, lepimectin, leptophos, lindane, lirimfos, lufenuron, lythidathion, malathion, malonoben, mazidox, mecarb am), mecarphon, menazon, mephosfolan, mercurous chloride, mesulfen, mesulfenfos, metaflumizone, metam, methacrifos, methamidophos, methidathion, methiocarb, methocrotophos, methomy l), methoprene, methoxychlor, methoxyfenozide, methyl bromide, methyl isothiocyanate, methyl chloroform, methylene chloride, metofluthrin, metolcarb, metoxadiazone, mevinphos, mexacarbate, milbemectin, milbemycinoxime, mipafo x), mirex, MNAF, monocrotophos, morphothion, moxidectin, naftalofos, naled, naphthalene, nicotine, nifluridide, nikkomycins, nitenpyram, nithiazine, nitrilacarb, novaluron, noviflumuron,Omethoate, oxamyl, oxydemeton methyl, oxydeprofos, oxydisulfoton, parathion, parathionmethyl, penfluron, pentachlorophenol, permethrin, phenkapton, phenothrin, phenthoate, phorate, phosalone, phosfolan, phosmet, phosnichlor, phosphamidon, phosphocarb, phoxim, phoxim methyl, pirimetaphos, pirimicarb, pirimiphos ethyl, pirimiphos methyl methyl), potassium arsenite, potassium thiocyanate, pp'DDT, prallethrin, precocene I, precocene II, precocene III, primidophos, proclonol, profenofos, profluthrin, promacyl, promecarb, propaphos, propargite, propetamphos, propoxur, prothidathion, prothiofos, prothoate, protrifenbute, pyraclofos, pyrafluprole, pyrazophos, pyresmethrin, pyrethrin I I), Bilin II, pyridaben, pyridalyl, pyridaphenthion, pyrifluquinazon, pyrimidifen, pyrimitate, pyriprole, pyriproxyfen, quassia,Quinalphos, quinalphos, methyl quinalphos methyl), quinothion, quantifies, rafoxanide, resmethrin, rotenone, ryania, sabadilla, schradan, selamectin, silafluofen, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulcofuron, sulfiram, sulfluramid, sulfotep, sulfur, sulfuryl fluoride, sulprofos, tauflumethrin fluvalinate), tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane, tetrachlorvinphos, tetradifon, tetramethrin, tetratranactin, tetrasul, thetacypermethrin ermethrin), thiacloprid, thiamethoxam, thicrofos, thiocarboxime, thiocyclam, thiodicarb, thiofanox, thiometon, thionazin, thioquinox, thiosultap, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, transpermethrin,triarathene, triazamate, triazophos, trichlorfon, trichlormetaphos 3, trichloronat, trifenofos, triflumuron, trimethacarb, triprene, vamidothion, vaniliprole, XMC, xylylcarb, zeta cypermethrin and zolaprofos.

[0152] Exemplary fungicides include, but are not limited to, acibenzolar, amidoamino acid fungicides, acypetacs, aldimorph, aliphatic nitrogen fungicides, allyl alcohols, amide fungicides, ampropylfos, anilazine, aniline fungicides, antibiotic fungicides, aromatic fungicides, aureofungin, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benzalkonium chloride, chloride), benzamacril, benzamide fungicides, benzamorf, benzoanilide fungicides, benzimidazole fungicides, benzimidazole precursor fungicides, benzimidazole carbamate fungicides, benzhydroxamic acid, benzothiazole fungicides, bethoxazin, binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S, Bordeaux mixture, boric acid, boscalid, bridged phenyl fungicides, bromuconazole, bupirimate, Burgundy mixture mixture), buthiobate, sec-butylamine, calcium polysulfide, captafol, captan, carbamate fungicides, carbamorph, phenylcarbamate fungicides, carbendazim, carboxin, carpropamid, carvone, Cheshunt mixture, chinomethionat, chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chlorodinitronaphthalene, chloroform,Chloroquinox, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, ciclopirox, climbazole, clotrimazole, conazole fungicides, conazole fungicides (imidazoles), conazole fungicides (triazoles), copper (II) acetate, copper (II) carbonate, (basic) copper fungicides, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper (II) sulfate, copper sulfate, (basic) copper zinc chromate, cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid, cyclic dithiocarbamate fungicides, cycloheximide, cyflufenam id), cymoxanil, cypendazole, cyproconazole, cyprodinil, dazomet, DBCP, debacarb, decafentin, dehydroacetic acid, dicarboximide fungicides, dichlofluanid, dichlone, dichlorophen, dichlorophenyl, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, diethyl pyrocarbonate, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole , Dakli-M, dinitrophenol fungicide, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon, dithiocarbamate fungicide, DNOC,dodemorph, dodicin, dodine, donatodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethylene oxide, 2,3-dihydroxypropylmercuric ethylmercury, ethylmercuric acetate, ethylmercuric bromide, ethylmercuric chloride, ethylmercuric phosphate, etridiazole, famox adone), fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, Fluconazole, Fludioxonil, Flumetover, Flumorph, Fluopicolide, Fluoroimide, Fluotrimazole, Fluoxastrobin, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Fluoxazolidinone fluxapyroxad, folpet, formaldehyde, fosetyl, fuberidazole, furaxyl, furametpyr, furamide fungicides, furaniline fungicides, furcarbanil, furconazole, cis-fluconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin, guazatine,halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen, hymexazol, imazalil, imibenconazole, imidazole fungicide, iminoctadine, inorganic fungicide, inorganic mercury fungicide, iodomethane, ipconazole, iprobenfos, iprodione, iprovalicarb, isopropyl alcohol, isoprothiolane, isovaledione, isopyrazam, kasugamycin, ketoconazole, kresoxim-methyl, lime sulfur sulfur), mancopper, mancozeb, maneb, mebenil, mecarbinzid, mepanipyrim, mepronil, mercuric chloride (abandoned), mercuric oxide (abandoned), mercurous chloride (abandoned), metalaxyl, metalaxyl-M (also known as Mefenoxam), metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl bromide, methyl isothiocyanate, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide (methylmercury pentachlorophenoxide), pentachlorophenoxide), metiram, metominostrobin, metrafenone, metsulfovax, milneb, morpholine fungicides, myclobutanil, myclozolin, N-(ethylmercury)-toluenesulfonanilide, nabam, natamycin, nystatin, β-nitrostyrene, nitrothal-isopropyl, nuarimol, OCH, octhilinone, ofurace, oprodione, organomercury fungicides, organophosphorus fungicides,Organotin fungicides (obsolete), orthophenyl phenol, orysastrobin, oxadixyl, oxathiin fungicides, oxazole fungicides, oxine copper, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, pentachlorophenol, penthiopyrad, phenylmercuriurea, phenylmercuric acetate, phenylmercuric chloride, phenylmercuric derivatives of catechol, phenylmercuric nitrate, phenylmercuric salicylate, phenylsulfonamide fungicides, phosdiphen, phosphites, phthalide, benzene o-Dicarboximide fungicides, picoxystrobin, piperalin, polycarbamates, polymer dithiocarbamate fungicides, polyoxins, polyoxorim, polysulfide fungicides, potassium azide, potassium polysulfide, potassium thiocyanate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propi neb), proquinazid, prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin, pyrazole fungicides, pyrazophos, pyridine fungicides, pyridinitril, pyrifenox, pyrimethanil, pyrimidine fungicides, pyroquilon, pyroxychlor, pyroxychlor pyroxyfur, pyrrole fungicide, quinacetol, quinazamid, quinconazole, quinoline fungicide, quinomethionate, quinone fungicide, quinoxaline fungicide, quinoxyfen, quintozene, rabenzazole, salicylanilide, silthiofam, silver, simeconazole, sodium azide,Sodium bicarbonate[2][3], sodium o-phenylphenol, sodium pentachlorophenol, sodium polysulfide, spiroxamine, streptomycin, strobilurin fungicides, sulfonanilide fungicides, sulfur, sulfonyl fluoride, sultropen, TCMTB, tebuconazole, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadiazole (thiadifluor), thiazole fungicides, thicyofen, thifluzamide, thymol, triforine, thiocarbamate fungicides, thiochlorfenphim, thiomersal, thiophanate, thiophanate-methyl, thiophene fungicides, thioquinox, thiram, tiadinil, tioxymid, tive do, tolclofos-methyl, tolnaftate, tolylfluanid, methyl methylmercuric acetate, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazine fungicides, triazole fungicides, triazoxide, tributyltin oxide, trichlamide, tricyclazole, triridemorph, triflumin floxystrobin), triflumizole, triforine, triticonazole, unclassified fungicides, undecylenic acid, uniconazole, uniconazole-P, urea fungicides, validamycin, valinamide fungicides, vinclozolin, voriconazole, zarilamid, zinc cyclohexane, zineb,Ziram and / or zoxamide.

[0153] In some embodiments, the composition of the presently disclosed subject matter is a pesticide / chloramphenicol-containing composition comprising a pesticide and a chloramphenicol-monoacid complex or mixture. In some embodiments, the pesticide is a herbicide, an insecticide, or a combination thereof.

[0154] In some embodiments, the composition of the presently disclosed subject matter is a fungicide / chloramphenicol-containing composition that includes a fungicide and a chloramphenicol-monoacid complex or mixture.

[0155] The amount of chlorpyrifos-monoacid complex or mixture in the pesticide / chlorpyrifos composition and / or the fungicide / chlorpyrifos composition can vary. In some embodiments, the amount of chlorpyrifos-monoacid complex or mixture is present at a level of 0.05-10 wt % (more preferably about 0.1 wt %-4 wt %, and most preferably about 0.2-2 wt %) based on the total weight of the pesticide / chlorpyrifos composition or the fungicide / chlorpyrifos composition as 100 wt %.

[0156] Exemplary classes of miticides include, but are not limited to, botanical miticides, bridged biphenyl miticides, carbamate miticides, carbamate oxime ester miticides, carbazate miticides, dinitrophenol miticides, formamidine miticides, isoxaline miticides, macrolide miticides, avermectin miticides, milbemycin miticides, milbemycin miticides, mite growth regulators, organochlorine miticides, organophosphate miticides, organothiophosphate miticides, phosphonate miticides, phosphoarmidothiolate miticides, organotin miticides, benzene sulfonamide miticides, pyrazole carboxamide miticides, pyrethroid ether miticides, quaternary ammonium miticides, oyrethroid ester miticides, pyrrole miticides, quinoxaline miticides, methoxyacrylate strobilurin miticides, Examples of miticides in these categories include, but are not limited to, botanical miticides - carvacrol, sanguinarine; bridged biphenyl miticides - azobenzene, benzoximate, benzyl benzoate, bromopropylate, chlorbenside, chlorfenethol, chlorfenson, chlorfensulphide, chlorobenzilate, chloropropylate, cyflumetofen, DDT, dicofol, diphenyl sulfone, chlorfenthrin ... sulfone), dofenapyn, fenson, fentrifanil, fluorbenside, genit, hexachlorophene, phenproxide, proclonol, tetradifon, tetrasul; carbamate miticides – benomyl, carbanolate, carbaryl, carbofuran, methiocarb, metolcarb, promacyl and propoxur;Carbamate oxime ester acaricides - aldicarb, butocarboxim, oxamyl, thiocarboxime and thiofanox; carbazate ester acaricides - bifenazate; dinitrophenol acaricides - binapacryl, dinex, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinopenton , dinosulfon, dinoterbon, DNOC; formamidine miticides - amitraz, chlordimeform, chloromebuform, formetanate, formparanate, medimeform, semiamitraz; isoxazoline miticides - afoxolaner, fluralaner, lotilaner , sarolanaer; macrolide acaricides - tetranactin; avermectin acaricides - abamectin, doramectin, eprinomectin, ivermectin, selamectin; milbemycin acaricides - milbemectin, milbemycin, oxime, moxidectin; mite growth regulators - clofentezine, ciprofloxacin cyromazine), diflovidazin, dofenapyn, fluazuron, flubenzimine, flucycloxuron, flufenoxuron, hexythiazox; organochlorine miticides - bromociclen, camphechlor, DDT, dienochlor, endosulfan, lindane;Organophosphorus acaricides - chlorfenvinphos, crotoxyphos, dichlorvos, heptenophos, mevinphos, monocrotophos, naled, TEPP, tetrachlorvinphos; Organothiophosphate acaricides - amidithion, amiton, azinphos-ethyl, azinphos-methyl, azothoate, benoxafos, bromophos, bromophos-ethyl, carbophenothion, chlorpyrifos, chlorthiophos, coumaphos, cyanthoate, demeton, oxodemeton, thiodemeton, methyl demeton, methylisodemeton, methylthiodemeton, sulfone demeton, dialifos, diazinon, dimethoate, dioxathion, disulphide ulfoton), endothion, ethion, ethoate-methyl, formothion, malathion, mecarbam, methacrifos, omethoate, oxydeprofos, oxydisulfoton, parathion, phenkapton, phorate, phosalone, phosmet, phosphomon stin), phoxim, pirimiphos-methyl, prothidathion, prothoate, pyrimitate, quinalphos, quintiofos, sophamide, sulfotep, thiometon, triazophos, trifenofos, vamidothion; phosphonate acaricide - trichlorfon;Thiophosphoramidate acaricides - isocarbophos, methamidophos, propetamphos; phosphodiamide acaricides - dimefox, mipafox, schradan; organotin acaricides - azocyclotin, cyhexatin, fenbutatin oxide, phostin; benzenesulfonamide acaricides - dichlofluanid; phthalimide acaricides - dialifos, phosmet; pyrazole acaricides - cyenopyrafen, fenpyroximate; phenylpyrazole acaricides - acetoprole, fipronil, vaniliprole; pyrazole carboxamide acaricides - Pyflubumide, tebufenpyrad; pyrethroid acaricides - acrinathrin, bifenthrin, brofluthrinate, cyhalothrin, cypermethrin, alpha-cypermethrin, fenpropathrin, fenvalerate , flucythrinate, flumethrin, fluvalinate, tau-fluvalinate, permethrin; pyrethroid ether acaricide - halfenprox; pyrimidifen acaricide - pyrimidifen; pyrrole acaricide - chlorfenapyr; quaternary ammonium acaricide - sanguinarine; quinoline Oxoline acaricides - chinomethionat, thioquinox; strobilurin acaricides - bifujunzhi, fluacrypyrim, flufenoxystrobin, pyriminostrobin; sulfite acaricides - aramite, propargite; tetronic acid acaricide - spirodiclofen;Tetrazine miticides - clofentezine, diflovidazin; thiazolidine miticides - flubenzimine, hexythiazox; thiocarbamate miticides - fenothiocarb; thiourea miticides - chloromethiuron, diafenthiuron; unclassified miticides - acequinocyl, acynonapyr, amidoflumet, arsenic trioxide oxide), clenpirin, closantel, crotamiton, cycloprate, cymiazole, disulfiram, etoxazole, fenazaflor, fenazaquin, fluenetil, mesulfen, MNAF, nifluridide, nikkomycins, pyridaben, sulfiram, sulfluramid, sulfur, thuringiensin, triarathene.

[0157] In some embodiments, the acaricide can also be selected from abamectin, acephate, acequinocyl, acetamiprid, aldicarb, allethrin, aluminum phosphide, aminocarb, amitraz, azadiractin, azinphos-ethyl, azinphos-methyl, Bacillus thuringiensis, huringiensis), bendiocarb, beta-cyfluthrin, bifenazate, bifenthrin, bomyl, buprofezin, calcium cyanide, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, chlorfenvinphos, chlorobenzilate, chloropicrin n), chlorpyrifos, clofentezine, chlorfenapyr, clothianidin, coumaphos, crotoxyphos, crotoxyphos + dichlorvos, cryolite, cyfluthrin, cyromazine, cypermethrin, DEET, deltamethrin, systemic acid, diazinon diazinon, dichlofenthion, dichloropropylene, dichlorvos, dicofol, dicrotophos, dieldrin, dienochlor, diflubenzuron, dikar, fungicides + miticides, dimethoate, chlorpyrifos, dinotefuran, dioxathion, disulfoton, emamectin benzoatebenzoate), endosulfan, endrin, esfenvalerate, ethion, ethoprop, ethylene dibromide, ethylene dichloride, etoxazole, famphur, fenitrothion, fenoxycarb, fenpropathrin, fenpyroximate, fensulfothion, fenthion, fenvalerate, flonicamid, flucythrinate, fluvalinate, fonofos, formetanate hydrochloride hydrochloride), gamma-cyhalothrin, halofenozide, hexakis, hexythiazox, hydramethylnon, calcium hydroxide, indoxacarb, imidacloprid, kerosene, kinoprene, 1ambda-cyhalothrin, lead arsenate, lindane, malathion, mephosfolan, metaldehyde, metam-sodium, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, parathion), mevinphos, mexacarbate, Milky DiseaseSpores), naled, naphthalene, nicotine sulfate, novaluron, oxamyl, oxydemeton-methyl, oxythioquinox, p-dichlorobenzene, parathion, PCP, permethrin, petroleum, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, piperonyl ether butoxide), pirimicarb, pirimiphos-methyl, profenolos, propargite, propetamphos, propoxur, pymetrozine, pyrethroid - synthetic: see allethrin, permethrin, fenvalerate, resmethrin, pyrethrum, pyridaben, pyriproxyfen, resmethrin, rotenone rotenone, s-methoprene, soap, pesticide, sodium fluoride, spinosad, spiromesifen, sulfotep, sulprofos, temephos, terbufos, tetrachlorvinphos, tetrachlorvinphos + dichlorvos, tetradifon, thiamethoxam, thiodicarb, toxaphene, tralomethrin, trimethacarb, and tebufenozide.

[0158] IV. Methods

[0159] In some embodiments, the chlorpyrifos-monoacid complex or mixture is used directly. In other embodiments, the chlorpyrifos-monoacid complex or mixture is formulated in a manner that makes it easy to use in a productive agricultural environment. The chlorpyrifos-monoacid complex or mixture used in these methods comprises the chlorpyrifos-monoacid complex or mixture as described above. The chlorpyrifos-monoacid complex or mixture can be used in methods such as the following:

[0160] A. Methods of improving plant growth and / or fertilizing the soil

[0161] B. Methods of inhibiting nitrification or ammonia release or emission

[0162] C. Methods to reduce the volatilization of chlorpyrifos

[0163] D. Methods to improve soil conditions

[0164] E. Method for preparing chlorpyrifos-monoacid complex

[0165] A. A method for improving plant growth comprises contacting a chlorpyrifos-monoacid complex or mixture as disclosed herein or a composition containing a chlorpyrifos-monoacid complex or mixture with soil. In some embodiments, a chlorpyrifos-monoacid complex or mixture as disclosed herein or a composition containing a chlorpyrifos-monoacid complex or mixture is applied to soil before the emergence of planted crops. In some embodiments, a chlorpyrifos-monoacid complex or mixture is applied to soil adjacent to a plant and / or located at the base of a plant and / or in the root zone of a plant.

[0166] The method for improving plant growth can also be applied to seeds in the form of liquid dispersions by using chlorpyrifos-monoacid complex or mixture or compositions containing chlorpyrifos-monoacid complex or mixture as seed coating, and the liquid dispersion forms dry residues when drying. In these embodiments, the seed coating provides chlorpyrifos-monoacid complex or mixture next to the seed when planting, so that chlorpyrifos-monoacid complex or mixture can bring into play its beneficial effect in the environment where it is most needed. That is, chlorpyrifos-monoacid complex or mixture provides an environment that is conducive to enhancing plant growth in the region around the desired plant where the effect can be positioned. In the case of seed, the coating containing chlorpyrifos-monoacid complex or mixture provides enhanced opportunities for seed germination, subsequent plant growth and the increase of plant nutrient utilization.

[0167] B. A method for inhibiting / reducing nitrification or ammonia release or emission in an affected area comprises applying a chlorpyrifos-monoacid complex or mixture or a composition containing the chlorpyrifos-monoacid complex or mixture to the affected area. The affected area may be soil adjacent to plants, fields, pastures, livestock or poultry enclosures, pet waste, manure collection areas, upright walls forming enclosures, or roofs that substantially cover the area, and in such cases, the chlorpyrifos-monoacid complex or mixture may be applied directly to the manure in the collection area. The chlorpyrifos-monoacid complex or mixture is preferably applied in the form of an aqueous dispersion having a pH of about 1-5 at a level of about 0.005-3 gallons per ton of manure.

[0168] C. The method of reducing the volatility of chlorpyrifos comprises compounding or mixing chlorpyrifos with a monoacid to form a chlorpyrifos-monoacid complex or mixture. The chlorpyrifos-monoacid complex or mixture is less volatile than chlorpyrifos not compounded or mixed with the monoacid. In some embodiments, the chlorpyrifos-monoacid complex or mixture reduces volatility by about 5% to about 40%, about 8% to about 35%, about 15% to about 35%, about 25% to about 35%, about 20% to about 30%, or about 10% to about 30% (or by at least about 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%, 31%, 32%, 33%, 34%, or 35%) compared to chlorpyrifos not complexed or mixed with the monoacid.

[0169] D. A method for improving soil conditions selected from the group consisting of nitrification process, urease activity and combinations thereof, the method comprising the step of applying an effective amount of the chlorpyrifos-monoacid complex or mixture or a composition containing the chlorpyrifos-monoacid complex or mixture to the soil. In some embodiments, the chlorpyrifos-monoacid complex or mixture is mixed with ammonia-containing solid, liquid or gaseous fertilizer, especially solid fertilizer; in the latter case, the chlorpyrifos-monoacid complex or mixture is applied to the surface of the fertilizer in the form of an aqueous dispersion and then dried so that the chlorpyrifos-monoacid complex or mixture is present on the solid fertilizer as a dry residue. The chlorpyrifos-monoacid complex or mixture is generally applied at a level of about 0.01-10% by weight, based on the total weight of the chlorpyrifos-monoacid complex or mixture / fertilizer product as 100% by weight. When the fertilizer is an aqueous liquid fertilizer, the chlorpyrifos-monoacid complex or mixture is added thereto and mixed. The chlorpyrifos-monoacid complex or mixture is preferably in the form of an aqueous dispersion and has a pH of about 3 at most.

[0170] E. A method for preparing a chlorpyrifos-monoacid complex or mixture, the method comprising contacting chlorpyrifos with one or more solvents to form a first mixture; contacting the first mixture with a monoacid to form a complex or mixture of chlorpyrifos and the monoacid.

[0171] In some embodiments, the above methods A, B and D include contacting the desired area with chlorpyrifos-monoacid complex or mixture at a rate of about 100 g to about 120 g of chlorpyrifos-monoacid complex or mixture per acre. In some embodiments, the chlorpyrifos-monoacid complex or mixture may be present in solution in an amount of about 0.5 lb to about 4 lb per U.S. gallon, or about 1 lb to about 3 lb per U.S. gallon, or about 2 lb per U.S. gallon. In some embodiments, the method comprises contacting the desired area at a rate of about 0.5 to about 4 qt. / A or about 1 to about 2 qt. / A.

[0172] Particular embodiments of the subject matter described herein include:

[0173] 1. A chlorpyrifos-monoacid complex, comprising chlorpyrifos complexed with a monoacid.

[0174] 2. The chlorpyrifos-monoacid complex according to embodiment 1, wherein the monoacid is selected from the group consisting of monocarboxylic acids, monosulfonic acids and monophosphonic acids.

[0175] 3. The chlorpyrifos-monoacid complex according to embodiment 1, wherein the monoacid is selected from the group consisting of monocarboxylic acids, monosulfonic acids and monophosphonic acids.

[0176] 4. A chlorpyrifos-monoacid complex, comprising chlorpyrifos complexed with a monoacid, wherein the monoacid is selected from the group consisting of monocarboxylic acids, monosulfonic acids and monophosphonic acids.

[0177] 5. The chlorpyrifos-monoacid complex according to any of the above embodiments, wherein the monoacid is substituted with an alkyl, alkenyl or aromatic ring system.

[0178] 6. The chlorpyrifos-monoacid complex according to embodiment 5, wherein the aromatic ring system is substituted by one or more of the following: -OR1, -C(=O)R2, -PO3H, -PO3R4, -SO3H, -SO3R4, -N(R3)(R4), -C1-C6 alkyl, halogen, -CN, -CF3, -NO2 and -CF3;

[0179] wherein R1 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl);

[0180] R2 is -H, -OH, -N(R4)(R4), -C1-C6 alkyl or -O(C1-C6 alkyl);

[0181] R3 is -H, -C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0182] R4 is -H or -C1-C6 alkyl.

[0183] 7. The chlorpyrifos-monoacid complex according to embodiment 6, wherein the aromatic ring system is substituted with one or more of -OR1, -C(=O)R2 and -C1-C6 alkyl;

[0184] wherein R1 is H, C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0185] R2 is H, -OH, C1-C6 alkyl or -O(C1-C6 alkyl).

[0186] 8. The chlorpyrifos-monoacid complex of any one of embodiments 5, 6 and 7, wherein the aromatic ring system is substituted by one or more of the following: -OH, -OCH3, -C(=O)H, -COOH, -C(=O)CH3, -C(=O)OCH3, -OC(=O)CH3, -CH3, -NH2, -NHCH3, -N(CH3)2 and -NC(=O)CH3.

[0187] 9. The chlorpyrifos-monoacid complex according to any one of embodiments 5, 6, 7 and 8, wherein the aromatic ring system comprises one or more heteroatoms selected from N, S and O.

[0188] 10. The chlorpyrifos-monoacid complex according to any one of embodiments 5, 6, 7, 8 and 9, wherein the aromatic ring system is an aryl ring system.

[0189] 11. The chlorpyrifos-monoacid complex according to embodiment 10, wherein the aromatic ring system is a benzene ring.

[0190] 12. The chlorpyrifos-monoacid complex according to any preceding embodiment, wherein the monoacid is a monocarboxylic acid.

[0191] 13. The chlorpyrifos-monoacid complex according to any of the above embodiments, wherein the monoacid is a compound of formula (I):

[0192]

[0193] wherein X1, X2, X3, X4 and X5 are independently selected from C and N, provided that no more than three of X1, X2, X3, X4 and X5 are N, and the three Ns are not directly adjacent to each other; and Y1, Y2, Y3, Y4 and Y5 are independently selected from H, -OR1, -C(=O)R2, C1-C6 alkyl, -N(R3)(R4) and are absent,

[0194] wherein R1 is H, C1-C6 alkyl or -C(=O)(C1-C6 alkyl);

[0195] R2 is -H, -OH, -N(R4)(R4), -C1-C6 alkyl or -O(C1-C6 alkyl);

[0196] R3 is H, C1-C6 alkyl or -C(=O)(C1-C6 alkyl); and

[0197] R4 is H or C1-C6 alkyl.

[0198] 14. The chlorpyrifos-monoacid complex according to embodiment 13, wherein X1, X2, X3, X4 and X5 are C.

[0199] 15. The chlorpyrifos-monoacid complex according to embodiment 13 or 14, wherein Y1, Y2, Y3, Y4 and Y5 are independently selected from H, -OH, -OCH3, -C(=O)OH, -C1-C6 alkyl and absent.

[0200] 16. The chlorpyrifos-monoacid complex according to any of the preceding embodiments, wherein the monoacid is selected from 3,4-dihydrobenzoic acid, 2,4-dihydrobenzoic acid, 2,5-dihydrobenzoic acid, vanillic acid and 3-4-dimethoxybenzoic acid.

[0201] 17. The chlorpyrifos-monoacid complex of any preceding embodiment, wherein the monoacid is methanesulfonic acid.

[0202] 18. The chlorpyrifos-monoacid complex of any preceding embodiment, wherein the chlorpyrifos and the monoacid are present in a weight ratio of about 5:1 to about 1:5.

[0203] 19. The chlorpyrifos-monoacid complex of any preceding embodiment, wherein the chlorpyrifos and the monoacid are present in a weight ratio of about 2.5:1 to about 1:2.5.

[0204] 20. The chlorpyrifos-monoacid complex of any preceding embodiment, wherein the chlorpyrifos-monoacid complex has a lower vapor pressure than the vapor pressure of chlorpyrifos not complexed with the monoacid.

[0205] 21. A composition comprising the chlorpyrifos-monoacid complex according to any one of the preceding embodiments and an organic solvent.

[0206] 22. The composition of embodiment 21, wherein the organic solvent is selected from the group consisting of aromatic solvents, halogenated solvents, glycol-based solvents, fatty acid-based solvents, acetate-containing solvents, ketone-containing solvents, and combinations thereof.

[0207] 23. The composition of embodiment 21 or 22, wherein the aromatic solvent is an aromatic hydrocarbon and the halogenated solvent is a halogenated aromatic hydrocarbon or a halogenated aliphatic hydrocarbon.

[0208] 24. The composition of any of embodiments 21, 22, and 23, wherein the organic solvent is selected from the group consisting of xylene, propylbenzene, mixed naphthalene and alkylnaphthalene, dimethyl sulfoxide, mineral oil, kerosene, dialkylamides of fatty acids, dimethylamides of fatty acids, dimethylamide of octanoic acid, 1,1,1-trichloroethane, chlorobenzene, esters of ethylene glycol derivatives, n-butyl ether of diethylene glycol, ethyl ether of diethylene glycol, methyl ether of diethylene glycol, acetate esters of methyl ether of dipropylene glycol, isophorone, trimethylcyclohexanone (dihydroisophorone), acetate esters, hexyl acetate, heptyl acetate, aromatics 100 (CAS No. 64742-95-6), aromatics 200 (CAS No. 64742-94-5), sulfones, ethylene glycol, polyethylene glycol, dipropylene glycol, Dow PT250, Dow PT700, PT250, triethylene glycol, tripropylene glycol, propylene carbonate, triacetin, AMD810, AMD3L, ADMA10, ADMA810, Polarclean and mixtures thereof.

[0209] 25. The composition of embodiment 21, wherein the organic solvent comprises dimethyl sulfoxide (DMSO).

[0210] 26. The composition of embodiment 21, wherein the organic solvent is xylene and dimethyl sulfoxide (DMSO).

[0211] 27. The composition of embodiment 21, wherein the organic solvent is dimethyl sulfoxide (DMSO) and Polarclean.

[0212] 28. The composition of embodiment 21, wherein the organic solvent is Polarclean.

[0213] 29. The composition of embodiment 21, wherein the organic solvent comprises DMSO, xylene, Polarclean and its combinations.

[0214] 30. A composition according to embodiment 21, wherein the organic solvent is xylene and dimethyl sulfoxide (DMSO), and the monoacid is selected from methanesulfonic acid, 2,4-dihydroxybenzoic acid (2,4-DHB acid), 2,5-dihydroxybenzoic acid (2,5-DHB acid), 3,4-dihydroxybenzoic acid (3,4-DHB acid), vanillic acid and 3,4-dimethoxybenzoic acid.

[0215] 31. The composition of embodiment 21, wherein the organic solvent is dimethyl sulfoxide (DMSO) and Polarclean, and the monoacid is selected from 3,4-dihydroxybenzoic acid (3,4-DHB acid), vanillic acid and 3,4-dimethoxybenzoic acid.

[0216] 32. The composition of embodiment 21, wherein the organic solvent is Polarclean, and the monoacid is selected from 2,4-dihydroxybenzoic acid (2,4-DHB acid) and 2,5-dihydroxybenzoic acid (2,5-DHB acid).

[0217] 33. The composition of embodiment 21, wherein the organic solvent is present in an amount ranging from about 20% w / w to about 80% w / w, based on the total weight of the composition.

[0218] 34. The composition of embodiment 21 wherein xylene is present in an amount ranging from about 20% w / w to about 80% w / w, based on the total weight of the composition.

[0219] 35. The composition of any preceding embodiment, wherein the chlorpyrifos-monoacid complex is present in a concentration of about 20% wt / wt to about 50% wt / wt, based on the total weight of the composition.

[0220] 36. The composition of any preceding embodiment, wherein the chlorpyrifos is present in a concentration of about 22% wt / wt to about 48% wt / wt, based on the total weight of the composition.

[0221] 37. The composition of any preceding embodiment, wherein the monoacid is present in an amount of about 10% wt / wt to about 50% wt / wt, based on the total weight of the composition.

[0222] 38. The composition of any preceding embodiment, wherein the chlorpyrifos is present in a concentration of about 22% wt / wt to about 48% wt / wt, based on the total weight of the composition.

[0223] 39. A composition according to any of the above embodiments, wherein the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, a monoacid in an amount of about 10% w / w to about 50% w / w, and an organic solvent in an amount of about 20% w / w to about 60% w / w, based on the total weight of the composition.

[0224] 40. The composition of any of the above embodiments, wherein the composition comprises chlorpyrifos in an amount of about 20% w / w to about 30% w / w, a monoacid selected from the group consisting of 3,4-DHB acid, 2,4-DHB acid, 2,5-DHB acid, vanillic acid, 3,4-dimethoxybenzoic acid, methanesulfonic acid, and any combination thereof, present in an amount of about 10% w / w to about 50% w / w, and a monoacid selected from the group consisting of xylene, DMSO, Polarclean and any combination of organic solvents.

[0225] 41. The composition of any preceding embodiment, wherein the composition exhibits lower volatility of chlorpyrifos compared to a chlorpyrifos composition in which chlorpyrifos does not form a complex with a monoacid.

[0226] 42. An agricultural composition comprising an agricultural product and the chlorpyrifos-monoacid complex according to any preceding embodiment.

[0227] 43. The agricultural composition of embodiment 42, further comprising an organic solvent.

[0228] 44. The agricultural composition of embodiment 43, wherein the organic solvent is selected from the group consisting of xylene, propylbenzene, mixed naphthalene and alkylnaphthalene, dimethyl sulfoxide, mineral oil, kerosene, dialkylamides of fatty acids, dimethylamides of fatty acids, dimethylamide of octanoic acid, 1,1,1-trichloroethane, chlorobenzene, esters of ethylene glycol derivatives, n-butyl ether of diethylene glycol, ethyl ether of diethylene glycol, methyl ether of diethylene glycol, acetate esters of methyl ether of dipropylene glycol, isophorone, trimethylcyclohexanone (dihydroisophorone), acetate esters, hexyl acetate, heptyl acetate, aromatics 100 (CAS No. 64742-95-6), aromatics 200 (CAS No. 64742-94-5), sulfone, ethylene glycol, polyethylene glycol, dipropylene glycol, Dow PT250, Dow PT700, PT250, triethylene glycol, tripropylene glycol, propylene carbonate, triacetin, AMD810, AMD3L, ADMA10, ADMA810, Polarclean and mixtures thereof.

[0229] 45. The agricultural composition of any one of embodiments 42, 43, and 44, wherein the organic solvent comprises dimethyl sulfoxide (DMSO).

[0230] 46. ​​The agricultural composition of any one of embodiments 42, 43, 44, and 45, wherein the organic solvent is xylene and dimethyl sulfoxide (DMSO).

[0231] 47. The agricultural composition of any one of embodiments 42, 43, 44 and 45, wherein the organic solvent is dimethyl sulfoxide (DMSO) and Polarclean.

[0232] 48. The agricultural composition of any one of embodiments 42, 43, 44 and 45, wherein the organic solvent is Polarclean.

[0233] 49. The agricultural composition of any one of embodiments 42, 43, 44 and 45, wherein the organic solvent comprises DMSO, xylene, Polarclean and its combinations.

[0234] 50. The agricultural composition of embodiment 43, wherein the organic solvent is xylene and dimethyl sulfoxide (DMSO), and the monoacid is selected from methanesulfonic acid, 2,4-dihydroxybenzoic acid (2,4-DHB acid), 2,5-dihydroxybenzoic acid (2,5-DHB acid), 3,4-dihydroxybenzoic acid (3,4-DHB acid), vanillic acid, and 3,4-dimethoxybenzoic acid.

[0235] 51. The agricultural composition of embodiment 43, wherein the organic solvent is dimethyl sulfoxide (DMSO) and Polarclean, and the monoacid is selected from 3,4-dihydroxybenzoic acid (3,4-DHB acid), vanillic acid and 3,4-dimethoxybenzoic acid.

[0236] 52. The agricultural composition of embodiment 43, wherein the organic solvent is Polarclean, and the monoacid is selected from 2,4-dihydroxybenzoic acid (2,4-DHB acid) and 2,5-dihydroxybenzoic acid (2,5-DHB acid).

[0237] 53. The agricultural composition of any preceding embodiment, wherein the agricultural product is selected from the group consisting of fertilizers, seeds, urease inhibiting compounds, nitrification inhibiting compounds, pesticides, herbicides, insecticides, fungicides, and miticides.

[0238] 54. The agricultural composition of any preceding embodiment, wherein the agricultural product is a fertilizer.

[0239] 55. The agricultural composition of any preceding embodiment, wherein the fertilizer is a liquid, solid, granular, fluid suspension, gas, or solubilized fertilizer.

[0240] 56. The agricultural composition of embodiment 55, wherein the chlorpyrifos-monoacid complex is applied to the surface of the solid or granular fertilizer in the form of a liquid dispersion that coats the solid or granular fertilizer and is in the form of a dry residue after drying.

[0241] 57. The agricultural composition of embodiment 55, wherein the fertilizer is in liquid form and the chlorpyrifos-monoacid complex is mixed with the liquid fertilizer.

[0242] 58. The agricultural composition of embodiment 55, wherein the chlorpyrifos-monoacid complex is present at a level of about 0.001 g to about 20 g per 100 g of the fertilizer; and / or is present at a level of about 0.01-10% w / w based on the total weight of the composition.

[0243] 59. The agricultural composition of embodiment 55, wherein the fertilizer is selected from the group consisting of starter fertilizers, phosphate-based fertilizers, nitrogen-containing fertilizers, phosphorus-containing fertilizers, potassium-containing fertilizers, calcium-containing fertilizers, magnesium-containing fertilizers, boron-containing fertilizers, zinc-containing fertilizers, manganese-containing fertilizers, copper-containing fertilizers, fertilizers containing molybdenum materials, and mixtures thereof.

[0244] 60. The agricultural composition of embodiment 59, wherein the fertilizer comprises urea and ammonium nitrate; and / or anhydrous ammonia; and / or is or contains urea; and / or contains one or more of: gypsum, a member of the kieserite group, a potassium product, potassium magnesium sulfate, elemental sulfur, and potassium magnesium sulfate.

[0245] 61. An agricultural composition according to embodiment 53, wherein the seed is coated with the chlorpyrifos-monoacid complex according to any of the above embodiments in the form of an aqueous dispersion to form a coated seed product, which provides a level of chlorpyrifos at about 0.001-10 weight percent based on the total weight of the coated seed product after drying.

[0246] 62. A method of fertilizing soil and / or improving plant growth and / or health, the method comprising contacting the chlorpyrifos-monoacid complex according to any preceding embodiment or the composition according to any preceding embodiment with the soil.

[0247] 63. A method for reducing the volatility of chlorpyrifos by complexing chlorpyrifos with a monobasic acid.

[0248] 64. The method of embodiment 63, wherein the volatilization is reduced by about 10% to about 30% compared to chlorpyrifos not complexed with the monoacid.

[0249] 65. A method of reducing atmospheric ammonia and / or nitrification, the method comprising applying the chlorpyrifos-monoacid complex of any preceding embodiment to an area subject to ammonia emissions and / or nitrification.

[0250] 66. A method of reducing atmospheric ammonia and / or nitrification, the method comprising applying a composition according to any preceding embodiment to an area subject to ammonia emissions and / or nitrification.

[0251] A method of inhibiting a soil condition selected from the group consisting of a nitrification process, urease activity, and combinations thereof, wherein the method comprises applying an effective amount of the chlorpyrifos-monoacid complex according to any of the above embodiments to the soil.

[0252] Examples

[0253] It should be understood that the following examples are provided by way of illustration only and nothing therein should be construed as limiting.

[0254] Example 1 :Study on the solubility of chlorpyrifos-monoacid complexes and mixtures in various solvent systems

[0255] Chlorpyrifos and monoacids were added to a solvent system containing two different solvents, as shown in Tables 1 and 2. The color of the resulting solution and the solubility of the chlorpyrifos complex in the solution were recorded. As already mentioned, the color changes as the chlorpyrifos-monoacid complex forms. The color change is due to the complex; this is a qualitative indicator of the stability of the complex. Generally, this stability is better at lower temperatures because (increased) thermal energy can make the complex unstable. Remaining soluble at lower temperatures indicates (possible) disruption of the order, which means that some formulations will not freeze. The intensity of the color and the color itself depend on the concentration of the monoacid and / or solvent and the choice of the monoacid and / or solvent. Especially for monoacids containing chromophores such as aromatic rings (see Table 2). Further, the solution was cooled to a lower temperature to observe the physical properties, as shown in Tables 1 and 2 (for procedures, see Example 4). The absence of observed freezing of the solution at lower temperatures for a longer period of time is a good initial indicator that these solutions can be suitable for low temperature field applications.

[0256] Table 1

[0257] Chlorpyrifos* 2.8 2.8 2.5 2.5 Methanesulfonic acid* 1.17 3,4-DHB acid* 1.87 Vanillic acid* 1.82 3,4-Dimethoxybenzoic acid* 1.97 Polarclean / DMSO*,** 6.03 5.33 5.68 5.53 Total amount in grams* 10 10 10 10 Chlorpyrifos content 28％ 28％ 25％ 25％ Solid content*** 39.70％ 46.70％ 43.20％ 44.70％ Observations Soluble Soluble Soluble Soluble o / n-20C 6 hours, -20C o / n-20C o / n-20C

[0258] d / n means no (freeze); o / n means overnight (e.g., about 8-14 hours); *Amounts are in grams, total 10 grams; ** Polarclean and DMSO are 1:1 by weight; *** solids content helps reduce solvent volume.

[0259] Table 2

[0260]

[0261]

[0262] d / n means no (freeze); o / n means overnight (e.g., about 8-14 hours); *Amounts are in grams, total 10 grams; **Xylene and DMSO are 1:1 by weight; ***Solids content helps to reduce the amount of solvent; aChlorpyrifos / solids content of the second sample.

[0263] Example 2 :Study on the volatility of chlorpyrifos-monoacid complexes and mixtures in various solvent systems

[0264] exist Several solutions containing chlorpyrifos (NP) and monoacids were prepared in Polarclean (PC). Chlorpyrifos was present at a concentration of 30% w / w, based on the total weight of the solution, and the monoacids 2,4-dihydroxybenzoic acid (2,4-DHBA) and 2,5-dihydroxybenzoic acid (2,5-DHBA) acids were present at 50% w / w (as the final complex), while 3,4-dihydroxybenzoic acid (3,4-DHBA) acid was present at a concentration of 43% w / w (as the final complex), based on the total weight of the solution. All solutions were equimolar with respect to the additive monoacids. It was noted that the solutions containing chlorpyrifos and monoacids underwent a color change (due to complex formation), while chlorpyrifos itself was a clear solution (see Figure 1 ). It is hypothesized that the different colors of solutions containing chlorpyrifos complexes imply unique absorption wavelengths and can be used as a tool to characterize such complexes.

[0265] The solution was heated at 55°C for 6 hours and any weight loss was recorded using thermogravimetric analysis (TGA; a technique that can accurately quantify weight loss) as shown in Table 3 below.

[0266] Table 3

[0267]

[0268]

[0269] *The amount of material used for TGA analysis was 22+3 mg.

[0270] The above data show that The average amount of weight loss of chlorpyrifos (NP) in Polarclean (PC) in six hours is 13.6%. However, chlorpyrifos mixed with isomeric monoacids as shown in Table 3 reduces the weight loss in six hours, which may be due to the complexation of chlorpyrifos with monoacids. More specifically, the solution containing chlorpyrifos and 2,4-DHBA only loses 8.7% (about 35% increase compared to chlorpyrifos alone); the solution containing chlorpyrifos and 2,5-DHBA only loses 9.7% (about 27% increase compared to chlorpyrifos alone), and the 3,4-DHBA complex only loses 8.7% (about 17% increase compared to chlorpyrifos alone). This data shows that the addition of monoacids reduces the weight loss of chlorpyrifos. In addition, these acids are phenolic and have antioxidant properties (can be used as food preservatives). Depending on the geometric structure, some acids will form stronger complexes, thereby reducing the weight loss of chlorpyrifos. The TGA mass loss observed above can be used as an indicator of the ability of various additives to complex with chlorpyrifos.

[0271] Example 3 :Study on the volatility of chlorpyrifos complexes in various solvent systems

[0272] exist Several solutions containing chlorpyrifos (NP) and monoacids were prepared in Polarclean (PC). Chlorpyrifos was present at a concentration of 30% w / w based on the total weight of the solution, and the monoacids methanesulfonic acid and 2,4-DHBA were present at 20% w / w (or less) based on the total weight of the solution. All solutions were equimolar with respect to the additive monoacids. It was noted that the solutions containing chlorpyrifos and the monoacid 2,4-DHBA underwent a color change (due to complex formation), while chlorpyrifos and methanesulfonic acid remained clear solutions (see Figure 2 ), indicating that no complex was formed.

[0273] The solution was heated at 55°C for 6 hours. A weight loss of 12.8% was recorded for methanesulfonic acid, while a weight loss of 13.3% was recorded for chloramphenicol. This shows that even the mixture can protect chloramphenicol from volatilization, albeit to a lesser extent (about 4%), compared to the system based on the complex chloramphenicol.

[0274] Example 4 : Solubility study of chlorpyrifos complexes / mixtures at lower temperatures.

[0275] The following step-by-step procedure was used to examine the stability and physical properties of various chlorpyrifos-monoacid complexes and mixtures:

[0276] 1) All solvent mixtures were prepared in advance by mixing the 2 solvents at 1:1 (by weight) and shaking the solvent mixture on a bottle roller for 30 minutes (Xy: DMSO and PC: DMSO. Xylene = Xy. PolarClean = PC).

[0277] 2) Prepare chlorpyrifos (NP) solution by adding chlorpyrifos to a glass vial, then add appropriate amount of solvent mixture and shake on a bottle roller for 30 minutes (or until homogenous).

[0278] 3) Chlorpyrifos: The monoacid solution was prepared by first adding the NPs, then the appropriate stoichiometric amount of monoacid, followed by the solvent mixture and shaking on a bottle roller for 30 minutes (or until homogenous).

[0279] 4) All dissolution procedures were performed at ambient temperature (on a bottle roller).

[0280] 5) The freeze-thaw procedure was performed by placing the appropriate vial in a refrigerator (-24°C) for 1 hour (freeze), placing on the bench for 1 hour (thaw), and doing this 3 times (total time slightly over 6 hours). Observations were made every hour. A total of 6 observations.

[0281] 6) Observation 1 means the state of the material observed after the first freeze (-24°C) and the first thaw. Therefore, there are two observations. Observations 2 (second freeze / thaw) and 3 (third freeze / thaw) are the same.

[0282] 7) NPs were dissolved in the two solvent mixture at 28% (by weight). The total amount of material used per vial (first column, below) was 7.5 g. The vial size was 20 mL capacity.

[0283] The results of the above studies are shown in Table 4 below.

[0284] Table 4

[0285] Material Observation 1 Observation 2 Observation 3 PC:DMSO Freeze, homogenize Freeze, homogenize Freeze, homogenize Xy:DMSO Freeze, homogenize Freeze, homogenize Freeze, homogenize PC with NP:DMSO Freeze, homogenize Freeze, homogenize Freeze, homogenize Xy containing NPs:DMSO Freeze, homogenize Freeze, homogenize Freeze, homogenize

[0286] Conclusions of Examples 1-4:

[0287] NPs and various monoacid complexes form homogeneous and transparent solutions at ambient temperature; some solutions may be colored due to the formation of complexes depending on the structural characteristics of the monoacids.

[0288] • Table 2 shows that while Xy:DMSO and Xy:DMSO containing NP froze (as seen in Table 4 above), the NP:2,4-DHB acid complex and the NP:vanillic acid complex (in Xy:DMSO) did not freeze (overnight at -20°C).

[0289] Based on the data in these tables, it is evident that the NP-monoacid complex imparts better solubility at lower temperatures while reducing the volatility of the NP; thereby improving NUE (nutrient use efficiency).

[0290] All technical and scientific terms used herein have the same meaning. Efforts have been made to ensure accuracy with respect to numbers used (eg, amounts, temperature, etc.) but some experimental errors and deviations should be accounted for.

[0291] Throughout this specification and claims, the words "comprise," "comprises," and "comprising" are used in a non-exclusive sense unless the context requires otherwise. It should be understood that the embodiments described herein include "consisting of" and / or "consisting essentially of" the embodiments.

[0292] As used herein, the term "about" when referring to a value is meant to encompass variations of ±5%, in some embodiments ±1%, in some embodiments ±0.5%, and in some embodiments ±0.1% from the specified amount, as such variations are suitable for performing the disclosed methods or employing the disclosed compositions.

[0293] Where a range of values ​​is provided, it is understood that each intervening value (to one-tenth of the unit of the lower limit) between the upper and lower limits of the range is encompassed, as well as any other stated or intervening value in the range, unless the context clearly dictates otherwise. The upper and lower limits of these smaller ranges that may be independently included in the smaller ranges are also encompassed, subject to any specifically excluded limits in the stated ranges. Where the stated range includes one or both of the limits, ranges excluding either or both of those included limits are also encompassed.

[0294] Many modifications and other embodiments set forth herein will occur to those skilled in the art having the benefit of the teachings presented in the foregoing description and the associated drawings. It should be understood, therefore, that the subject matter is not limited to the specific embodiments disclosed, and that modifications and other embodiments are intended to be included within the scope of the appended claims. Although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.

Claims

1. A nitrapyrin-monoacid complex, comprising nitrapyrin complexed with a monoacid, wherein an acidic functional group of the monoacid is associated with the nitrapyrin to form a complex, and the monoacid is 2,4-dihydroxybenzoic acid. 2 . The chlorpyrifos-monoacid complex according to claim 1 , wherein the chlorpyrifos and the monoacid are present in a weight ratio of 5:1 to 1:

5.

3. A composition comprising the chlorpyrifos-monoacid complex according to claim 1 and an organic solvent, The organic solvents include dimethyl sulfoxide (DMSO), xylene, Rhodiasolv® Polarclean and combinations thereof.

4. The composition of claim 3, wherein the organic solvent is Rhodiasolv® Polarclean.

5. The composition of claim 3, wherein the organic solvent is present in an amount of 20% w / w to 80% w / w based on the total weight of the composition.

6. The composition of claim 3, wherein chlorpyrifos is present in an amount of 22% w / w to 48% w / w, based on the total weight of the composition.

7. The composition of claim 3, wherein the monoacid is present in an amount of 10% w / w to 50% w / w based on the total weight of the composition.

8. The composition of claim 3, wherein the chlorpyrifos-monoacid complex is present in a concentration of 20% wt / wt to 50% wt / wt based on the total weight of the composition.

9. The composition of claim 3, wherein the composition comprises chlorpyrifos in an amount of 20% w / w to 30% w / w, the monoacid in an amount of 10% w / w to 50% w / w, and the organic solvent in an amount of 20% w / w to 60% w / w, based on the total weight of the composition. 10 . An agricultural composition comprising an agricultural product and the chlorpyrifos-monoacid complex according to claim 1 .

11. The agricultural composition of claim 10, wherein the agricultural product is selected from the group consisting of fertilizers, seeds, urease inhibiting compounds, nitrification inhibiting compounds, and pesticides.

12. The agricultural composition of claim 11, wherein the pesticide is selected from the group consisting of herbicides, insecticides, fungicides and miticides.

13. The agricultural composition of claim 11, wherein the agricultural product is a fertilizer, wherein the fertilizer is a liquid or a solid.

14. The agricultural composition of claim 13, wherein the liquid fertilizer is a fluid suspension.

15. The agricultural composition according to claim 13, wherein the chlorpyrifos-monoacid complex is applied to the surface of a solid fertilizer in the form of a liquid dispersion which coats the solid fertilizer and is in the form of a dry residue after drying; or wherein the fertilizer is in liquid form and the chlorpyrifos-monoacid complex is mixed with the liquid fertilizer.

16. An agricultural composition according to claim 13 or 15, wherein the solid fertilizer is a granular fertilizer.

17. The agricultural composition of claim 11, wherein the chlorpyrifos-monoacid complex is present at a level of 0.001 g to 20 g per 100 g of the fertilizer; and / or at a level of 0.01-10% w / w based on the total weight of the composition.

18. The agricultural composition of claim 11, wherein the fertilizer is selected from the group consisting of nitrogen-containing fertilizers, phosphorus-containing fertilizers, potassium-containing fertilizers, calcium-containing fertilizers, magnesium-containing fertilizers, boron-containing fertilizers, zinc-containing fertilizers, manganese-containing fertilizers, copper-containing fertilizers, fertilizers containing molybdenum materials, and mixtures thereof.

19. The agricultural composition of claim 11, wherein the fertilizer comprises urea and ammonium nitrate; and / or, the fertilizer comprises anhydrous ammonia; and / or, the fertilizer is urea or contains urea; and / or, the fertilizer contains one or more of the following: gypsum, potash products.

20. The agricultural composition of claim 19, wherein the potassium product is magnesium potassium sulfate.

21. The agricultural composition of claim 11, wherein the seed is coated with the chlorpyrifos-monoacid complex of claim 1 in the form of an aqueous dispersion to form a coated seed product, the coated seed product providing 0.001-10 wt% of chlorpyrifos based on the total weight of the coated seed product after drying thereof.

22. A method of fertilizing soil and / or improving plant growth and / or health, the method comprising contacting a chlorpyrifos complex with the soil, the chlorpyrifos complex comprising chlorpyrifos complexed with 2,4-dihydroxybenzoic acid.

23. A method of reducing atmospheric ammonia and / or nitrification, the method comprising applying the chlorpyrifos-monoacid complex of claim 1 to an area subject to ammonia emissions and / or nitrification.

24. A method of reducing atmospheric ammonia and / or nitrification, the method comprising applying a composition according to claim 3 to an area subject to ammonia emissions and / or nitrification.

25. A method of inhibiting a soil condition selected from the group consisting of: a nitrification process, urease activity, and a combination thereof, wherein the method comprises applying an effective amount of the chlorpyrifos-monoacid complex of claim 1 to the soil.

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