Agricultural preparations

Abstract

Various embodiments of the present invention relate to formulations that can be used in the agricultural industry. In one aspect, the agricultural formulation comprises at least one agricultural active ingredient in an amount of 1 wt % to up to 80 wt % based on the total weight of the formulation and an alkyl furan ester solvent of Formula 1, wherein the formulation comprises 5 wt % to up to 80 wt % of the alkyl furan ester solvent.

Description

Technical Field

[0001] The present invention relates to formulations that can be used in the agricultural industry. Background Art

[0002] Organic solvents are widely used in the agricultural industry to realize suitable delivery systems for water-insoluble active ingredients (such as pesticides and fertilizer stabilizers). It is expected that solvents with more concentrated solutions of many insecticide active ingredients are provided to develop economical formulations. For example, it is generally expected that 20% by weight or more of active ingredients are solubilized. In addition, in the agricultural industry, solvents with high polarity and low water solubility are particularly interested, which makes it possible to prepare emulsifiable concentrates. Generally, emulsifiable concentrates are concentrated solutions of pesticides in organic solvents, which may further contain suitable surfactants, including emulsifiers, so that when mixed with relatively large volumes of water, they will produce stable oil-in-water emulsions for application (such as by spraying) to target sites. In addition to high solubilizing power and low water solubility, it is also increasingly preferred to have a solvent with sustainable properties combining renewable carbon content with low ecological and human toxicity, so that the environmental impact of agricultural products and health issues is minimized.

[0003] It would be desirable to have alternative solvents that could provide high solubility for agricultural active ingredients, such as pesticides and fertilizers, that have attractive sustainability attributes (eg, no or at least reduced health and environmental issues). Summary of the invention

[0004] The present invention provides agricultural formulations that provide high solubility for agricultural active ingredients and low water solubility. In some embodiments, such formulations have attractive sustainability attributes, such as being from renewable sources and having low toxicity.

[0005] In one aspect, the agricultural formulation comprises at least one agriculturally active ingredient in an amount of 1 wt % to up to 80 wt %, based on the total weight of the formulation; and

[0006] Alkyl furan ester solvent according to Formula 1:

[0007]

[0008] Where R 1 is a methyl group, an ethyl group or a straight or branched alkyl group having 3 to 12 carbon atoms, and wherein the formulation comprises 5 wt % to as much as 80 wt % of the alkyl furan ester solvent. In some embodiments, the formulation is in the form of an emulsifiable concentrate.

[0009] These and other embodiments are described in more detail in the Detailed Description. DETAILED DESCRIPTION

[0010] As used herein, “a,” “an,” “the,” “at least one,” and “one or more” can be used interchangeably.

[0011] The terms "comprising", "including", "having" and their derivatives are not intended to exclude the presence of any additional components, steps or procedures, whether or not they are specifically disclosed. For the avoidance of any doubt, all compositions claimed by using the term "comprising" may include one or more additional compounds unless otherwise stated. In contrast, the term "consisting essentially of" excludes any other components, steps or procedures from the scope of any subsequent description, except those that are not necessary for operability. The term "consisting of" excludes any components, steps or procedures that are not specifically described or listed. Unless otherwise stated, the term "or" refers to members listed individually and in any combination. The use of the singular includes the use of the plural, and vice versa.

[0012] Also herein, numerical ranges recited by endpoints include all numbers subsumed within the range (e.g., 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, etc.). For purposes of the present invention, it is understood that numerical ranges are intended to include and support all possible subranges included within that range, consistent with what is understood by one of ordinary skill in the art. For example, a range from 1 to 100 is intended to express 1.01 to 100, 1 to 99.99, 1.01 to 99.99, 40 to 60, 1 to 55, etc.

[0013] Unless stated to the contrary, implicit from the context, or customary in the art, all parts and percentages are based on weight and all test methods are current as of the filing date of this disclosure.

[0014] When a compound (e.g., an active ingredient) is characterized as being soluble in a solvent (e.g., "a compound soluble in N,N-dialkyl fatty amides," "a compound soluble in aromatic ketones," "a compound soluble in alkyl ketones," "a compound soluble in cyclic ketones," "a compound soluble in aromatic hydrocarbon solvents," etc.), such terms mean that the compound is soluble in the specified solvent under ambient conditions, i.e., 23° C. and atmospheric pressure. In this case, solubility is defined by the approximate volume of solvent in milliliters (mL) required to dissolve 1 gram (g) of solute. Table 1 provides an overview of common solubility descriptions.

[0015] Table 1

[0016] describe Volume of solvent required to dissolve 1g of solute (mL) Very soluble Less than 1 Soluble 1 to 10 Soluble 10 to 30 Poorly soluble 30 to 100 Slightly soluble 100 to 1000 Very slightly soluble 1,000 to 10,000 Almost insoluble More than 10000

[0017] The method for measuring the solubility of a compound (e.g., an active ingredient) involves dissolving a solid solute in a solvent using stirring or shaking under specified conditions of temperature and time. The saturated solution is then separated from the solid using filtration. The concentration of the solute in the saturated solution is determined by analysis using ultraviolet (UV) spectroscopy, high pressure liquid chromatography using evaporative light scattering, UV or mass spectrometry detection, or NMR spectroscopy.

[0018] "Aromatic hydrocarbons", "aromatic hydrocarbons", "aryl hydrocarbons" and similar terms refer to hydrocarbons having sigma bonds and delocalized pi electrons between carbon atoms forming a single or multiple rings. Examples include, but are not limited to, benzene, toluene, naphthalene, and the like.

[0019] "Hydrocarbon" and like terms refer to chemical compounds consisting solely of carbon and hydrogen atoms.

[0020] "Solution" and similar terms refer to a homogeneous composition that (1) is variable, i.e., can contain varying concentrations of a solute in a solvent; (2) all but one of the components are present in their simplest units (e.g., molecules); and (3) can be separated into two or more pure substances by physical methods. In the context of the present invention, a solution refers to a liquid composition.

[0021] "Composition" and like terms mean a mixture or blend of two or more components.

[0022] "Emulsion" and like terms refer to a mixture of two or more liquids that are normally immiscible (unmixable or unadmixable) with each other, ie, the liquids do not form a solution.

[0023] "Emulsifiable concentrate" and like terms refer to formulations where the concentrate is typically diluted in water to form a stable emulsion. "Stable" and like terms mean that the emulsion will exhibit little, if any, degradation within 24 hours under ambient conditions, e.g., 23°C and atmospheric pressure.

[0024] In the context of the compositions of the present invention, "free of aromatic hydrocarbon solvents" and similar terms mean that the composition contains less than (<) 5, or <4, or <3, or <2, or <1, ​​or <0.5, or <0.1, or <0.05, or <0.01 wt % of aromatic hydrocarbons, which can dissolve aromatic hydrocarbon-soluble compounds such as pyrethroids, organophosphates, organosulfites, carbamates, cyclohexanedione, isoxazoles, phenoxy, chlorophenoxyacetic acid, aniline, chloroacetanilide, chloromethoxybenzoic acid, oxyacetanilide, strobilurin, triazoles, triazapentadiene, synthetic auxins, aryloxyphenoxypropionates, benzofurans, pyrimidines, phenylpyrazoles, phenylureas, diphenyl ethers, hydroxybenzonitrile, thiophosphoric triamides and chloropyridines under ambient conditions (23°C and atmospheric pressure). Any such amount of aromatic hydrocarbons in the composition is generally present as a contaminant and does not have any significant effect on the formation, maintenance and intended use of the composition. In one embodiment, "free of aromatic hydrocarbon solvents" means that the composition does not contain any amount of such solvents as measured by conventional gas chromatography (GC) or high pressure liquid chromatography (HPLC).

[0025] In the context of the compositions of the present invention, "free of N,N-dialkyl fatty amide solvent" and similar terms mean that the composition contains less than (<) 5, or <4, or <3, or <2, or <1, ​​or <0.5, or <0.1, or <0.05, or <0.01 wt % of N,N-dialkyl fatty amide, which can dissolve compounds such as pyrethroids, organophosphates, organosulfites, carbamates, cyclohexanedione, isoxazoles, phenoxy, chlorophenoxyacetic acid, aniline, chloroacetanilide, chloromethoxybenzoic acid, oxyacetanilide, strobilurin, triazoles, triazapentadiene, synthetic auxins, aryloxyphenoxypropionates, benzofurans, pyrimidines, phenylpyrazoles, phenylureas, diphenyl ethers, hydroxybenzonitrile, thiophosphoric triamides and chloropyridines under ambient conditions (23°C and atmospheric pressure). Any such amount of N,N-dialkyl fatty amide in the composition is generally present as a contaminant and does not have any significant effect on the formation, maintenance and intended use of the composition. In one embodiment, "free of N,N-dialkyl fatty amide solvent" means that the composition does not contain any amount of such solvent as measured by conventional gas chromatography (GC) or high pressure liquid chromatography (HPLC).

[0026] In the context of the compositions of the present invention, "free of aromatic, alkyl and cyclic ketone solvents" and similar terms mean that the composition contains less than (<) 5, or <4, or <3, or <2, or <1, ​​or <0.5, or <0.1, or <0.05, or <0.01 wt % of aromatic, alkyl and cyclic ketone solvents, which can dissolve compounds such as pyrethroids, organophosphates, organosulfites, carbamates, cyclohexanedione, isoxazoles, phenoxy, chlorophenoxyacetic acid, aniline, chloroacetanilide, chloromethoxybenzoic acid, oxyacetanilide, strobilurin, triazoles, triazapentadiene, synthetic auxins, aryloxyphenoxypropionates, benzofurans, pyrimidines, phenylpyrazoles, phenylureas, diphenyl ethers, hydroxybenzonitrile, thiophosphoric triamides and chloropyridines under ambient conditions (23°C and atmospheric pressure). Any such amount of aromatic, alkyl and cyclic ketone solvents in the composition is usually present as a contaminant and does not have any significant effect on the formation, maintenance and intended use of the composition. In one embodiment, "free of aromatic, alkyl and cyclic ketone solvents" means that the composition does not contain any amount of such solvents measured by conventional gas chromatography (GC) or high pressure liquid chromatography (HPLC).

[0027] Embodiments of the present invention generally relate to agricultural formulations comprising at least one agriculturally active ingredient and an alkyl furan ester solvent according to Formula 1, as further described herein. In some embodiments, such formulations may be emulsifiable concentrates. For example, the formulation may comprise an agriculturally active ingredient, such as a pesticide, a fertilizer stabilizer, and / or others. In one embodiment, the agricultural formulation of the present invention comprises at least one agriculturally active ingredient and an alkyl furan ester solvent according to Formula 1 in an amount of 1 wt % to up to 80 wt %, based on the total weight of the formulation:

[0028]

[0029] Where R 1 is a methyl group, an ethyl group, or a straight or branched alkyl group having 3 to 12 carbon atoms, and wherein the formulation comprises 5 wt % to as much as 80 wt % of the alkyl furan ester solvent. 1 is an ethyl group. In some embodiments, the agricultural formulation is in the form of an emulsifiable concentrate.

[0030] In some embodiments, the agricultural formulation comprises less than 50% by weight of a co-solvent. In such embodiments, the co-solvent comprises at least one of an N,N-dialkyl fatty amide solvent, an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, an aromatic ketone, an alkyl ketone, a cyclic ketone solvent, a glycol ether solvent, a seed oil solvent, a fatty acid ester solvent, or a combination thereof.

[0031] In some embodiments, the agricultural active ingredient is soluble in at least one of the following: N,N-dialkyl fatty amides, aromatic ketones, alkyl ketones, cyclic ketones, or aromatic hydrocarbon solvents. In some embodiments, the agricultural formulation comprises less than 50% by weight of an aromatic hydrocarbon solvent. In some such embodiments, the agricultural formulation is free of an aromatic hydrocarbon solvent.

[0032] In some embodiments, the agricultural active ingredient is soluble in at least one of: an N,N-dialkyl fatty amide, an aromatic ketone, an alkyl ketone, a cyclic ketone, or an aromatic hydrocarbon solvent. In some embodiments, the agricultural formulation comprises less than 50% by weight of an N,N-dialkyl fatty amide solvent. In some such embodiments, the agricultural formulation is free of an N,N-dialkyl fatty amide solvent.

[0033] In some embodiments, the agricultural active ingredient is soluble in at least one of the following: N,N-dialkyl fatty amides, aromatic ketones, alkyl ketones, cyclic ketones, or aromatic hydrocarbon solvents. In some such embodiments, the agricultural formulation contains less than 50% by weight of aromatic ketones, alkyl ketones, and cyclic ketone solvents. In some such embodiments, the agricultural formulation is free of aromatic ketones, alkyl ketones, and cyclic ketone solvents.

[0034] In some embodiments, the agriculturally active ingredient is at least one of: a pyrethroid, an organophosphate, an organosulfite, a carbamate, a cyclohexanedione, an isoxazole, a phenoxy group, a chlorophenoxyacetic acid, an aniline, a chloroacetanilide, a chloromethoxybenzoic acid, an oxyacetanilide, a strobilurin, a triazole, a triazapentadiene, a synthetic auxin, an aryloxyphenoxypropionate, a benzofuran, a pyrimidine, a phenylpyrazole, a phenylurea, a diphenyl ether, a hydroxybenzonitrile, a thiophosphoric triamide, and a chloropyridine.

[0035] In some embodiments, the agriculturally active ingredient is at least one of bifenthrin, tebuconazole, 2-methyl-4-chlorophenoxyacetic acid, 2,4-dichlorophenoxyacetic acid, N-(n-butyl)thiophosphoric triamide, dicamba acid, and chlorpyrifos.

[0036] In some embodiments, the agricultural formulations of the present invention further comprise one or more of the following: a surfactant, an emulsifier, a dispersant, a wetting agent, an adjuvant, an antioxidant, a rheology modifier, an antifreeze agent, or a colorant, wherein the one or more of the surfactant, emulsifier, dispersant, wetting agent, adjuvant, antioxidant, rheology modifier, antifreeze agent, or colorant comprises greater than zero to less than or equal to 15% by weight of the composition.

[0037] Alkyl furan ester solvent

[0038] The agricultural formulation of the present invention comprises an alkyl furan ester solvent according to Formula 1:

[0039]

[0040] Where R 1 is a methyl group, an ethyl group, or a straight or branched alkyl group having 3 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, the alkyl furan ester solvent is methyl 2-furoate, ethyl 2-furoate, isopropyl 2-furoate.

[0041] In one embodiment, the alkyl furan ester solvent is methyl 2-furoate. An example of a methyl 2-furoate that can be used in some embodiments of the present invention is Methyl 408, commercially available from xF Technologies Inc.

[0042] In one embodiment, the alkyl furan ester solvent is ethyl 2-furoate. An example of ethyl 2-furoate that can be used in some embodiments of the present invention is Ethyl 408, commercially available from xF Technologies Inc.

[0043] In one embodiment, the alkyl furan ester solvent is isopropyl 2-furoate. An example of isopropyl 2-furoate that can be used in some embodiments of the present invention is Isopropyl 408, commercially available from xF Technologies Inc.

[0044] In some embodiments, the alkyl furan ester solvent is the only solvent used in the agricultural formulation.

[0045] In some embodiments, the agricultural formulation comprises 5 wt % to up to 80 wt % of the alkyl furan ester solvent, based on the total weight of the formulation. In some embodiments, the alkyl furan ester solvent of Formula 1 accounts for greater than or equal to (≥) 5, ≥20, ≥30, ≥40, ≥50, ≥60, ≥70, or ≥75 weight percent (wt %) of the agricultural formulation, based on the total weight of the formulation. In some embodiments, the alkyl furan ester solvent of Formula 1 accounts for less than or equal to ≤80, ≤75, ≤70, ≤60, ≤50, ≤40, ≤30, or ≤20 of the agricultural formulation, based on the total weight of the formulation.

[0046] In some embodiments, the agricultural formulation can provide a higher concentration of agricultural active ingredients. In some such embodiments, the alkyl furan ester solvent of Formula 1 above accounts for greater than or equal to (≥) 10, ≥20, ≥30, ≥40 or ≥45 weight percent (wt%) of the agricultural formulation. In some embodiments, the alkyl furan ester solvent of Formula 1 accounts for less than or equal to (≤) 50 wt%, ≤45 wt%, ≤40 wt%, ≤35 wt% or ≤30 wt% of the agricultural formulation.

[0047] In some embodiments, the alkyl furan ester solvents of Formula 1 described herein may also reduce or eliminate the use of undesirable solvents that are harmful to the body, humans, and / or the environment in some applications.

[0048] Agricultural active ingredients

[0049] In addition to the alkyl furanyl ester solvent of Formula 1, the agricultural formulation of the present invention further comprises an agriculturally active ingredient.

[0050] In some embodiments, the agriculturally active ingredient is soluble in at least one of the following solvents: N,N-dialkyl fatty amide solvents, aromatic hydrocarbon solvents, aliphatic hydrocarbon solvents, aromatic ketones, alkyl ketones, cyclic ketone solvents, glycol ether solvents, seed oil solvents, or fatty acid ester solvents, or combinations thereof. As used herein, "alkyl ketone" is defined according to Formula 2:

[0051]

[0052] Where R 1 and R 2 is independently a straight or branched chain alkyl group containing only carbon atoms and hydrogen atoms. According to the definition of Formula 2, the only functional group in the alkyl ketone is the ketocarbonyl group, and the only heteroatom in the alkyl ketone is the carbonyl oxygen atom.

[0053] The solubility of the compound in one or more of these solvents is important because the alkyl furan ester solvents of Formula 1 herein can be used as ideal substitutes for such solvents. Typically, agricultural active ingredients are compounds used for one or more agricultural functions, such as pesticides, insecticides, herbicides, fungicides, fertilizer additives, etc. These agricultural active ingredients are generally insoluble in water and include, but are not limited to: pyrethroids, organophosphates, organosulfites, carbamates, cyclohexanediones, isoxazoles, phenoxy, chlorophenoxyacetic acid, aniline, chloroacetanilide, chloromethoxybenzoic acid, oxyacetanilide, strobilurin, triazole, triazapentadiene, synthetic auxin, aryloxyphenoxypropionate, benzofuran, pyrimidine, phenylpyrazole, phenylurea, diphenyl ether, hydroxybenzonitrile, thiophosphoric acid triamide and chloropyridine. In some embodiments, the compound soluble in N,N-dialkyl fatty amide solvent, aromatic hydrocarbon solvent, aliphatic hydrocarbon solvent, aromatic ketone, alkyl ketone, cyclic ketone solvent, glycol ether solvent, seed oil solvent or fatty acid ester solvent or a combination thereof is at least one of bifenthrin, tebuconazole, 2-methyl-4-chlorophenoxyacetic acid, 2,4-dichlorophenoxyacetic acid, N-(n-butyl) thiophosphoric triamide, dicamba acid and chlorpyrifos. Specific fertilizer additives include, but are not limited to, N-(n-butyl) thiophosphoric triamide and chlorpyrifos.

[0054] The amount of agricultural active ingredients to be used in embodiments of the agricultural formulations of the present invention may depend on many factors, including, but not limited to, the specific active ingredient used, whether the formulation contains multiple active ingredients, whether the formulation is an emulsifiable concentrate, the intended use of the formulation, and other factors known to those of ordinary skill in the art based on the teachings herein. In some embodiments, the agricultural formulation contains from 1% to as much as 80% by weight of the agricultural active ingredient, based on the total weight of the formulation.

[0055] In some embodiments, the agricultural formulation comprises greater than (>) 5, or greater than or equal to (≥) 10, or ≥ 15 weight percent (wt %) of the agricultural active ingredient based on the total weight of the formulation. In some embodiments, the agricultural formulation comprises less than or equal to (≤) 20 wt % of the agricultural active ingredient based on the total weight of the formulation.

[0056] In some embodiments, the agricultural formulation can provide a higher concentration of agricultural active ingredients. In some such embodiments, the agricultural formulation comprises greater than (>) 20, or greater than or equal to (≥) 25, ≥30, ≥35, ≥40, or ≥45 weight percent (wt%) of the agricultural active ingredient based on the total weight of the formulation. In some embodiments, the agricultural formulation comprises less than or equal to (≤) 50 weight % of the agricultural active ingredient based on the total weight of the formulation.

[0057] Other solvents

[0058] As described above, in some embodiments, the alkyl furan ester solvent of Formula 1 is the only solvent used in the agricultural formulation of the present invention. However, in some embodiments, the agricultural formulation of the present invention also includes a co-solvent (in addition to the alkyl furan ester solvent of Formula 1). When present, the co-solvent accounts for less than 50% by weight of the agricultural formulation based on the total weight of the formulation.

[0059] In some embodiments, the co-solvent comprises at least one of: an N,N-dialkyl fatty amide solvent, an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, an aromatic ketone, an alkyl ketone, a cyclic ketone solvent, a glycol ether solvent, a seed oil solvent, a fatty acid ester solvent, or a combination thereof.

[0060] In some embodiments, the agricultural formulations of the present invention contain less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of N,N-dialkyl fatty amide solvents, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain N,N-dialkyl fatty amide solvents.

[0061] In some embodiments, the agricultural formulations of the present invention contain less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of aromatic hydrocarbon solvents, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain aromatic hydrocarbon solvents.

[0062] In some embodiments, the agricultural formulations of the present invention contain less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of aromatic ketone solvents, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain aromatic ketone solvents.

[0063] In some embodiments, the agricultural formulations of the present invention contain less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of an alkyl ketone solvent, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain an alkyl ketone solvent.

[0064] In some embodiments, the agricultural formulations of the present invention comprise less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of a cyclic ketone solvent, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain a cyclic ketone solvent.

[0065] In some embodiments, the agricultural formulations of the present invention contain less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤ 30 wt%, or ≤ 20 wt%, or ≤ 10 wt%, or ≤ 5 wt% of aromatic ketones, alkyl ketones, and cyclic ketone solvents, based on the total weight of the formulation. In one embodiment, the agricultural formulations of the present invention do not contain aromatic ketones, alkyl ketones, and cyclic ketone solvents.

[0066] In some embodiments, the total amount of N,N-dialkyl fatty amide solvents, aromatic ketone solvents, alkyl ketone solvents, cyclic ketone solvents, and aromatic hydrocarbon solvents in the agricultural formulation of the present invention is less than (<) 50 wt%, or less than or equal to (≤) 40 wt%, or ≤30 wt%, or ≤20 wt%, or ≤10 wt%, or ≤5 wt%. In one embodiment, the agricultural formulation of the present invention does not contain N,N-dialkyl fatty amide solvents, aromatic ketone solvents, alkyl ketone solvents, cyclic ketone solvents, and aromatic hydrocarbon solvents.

[0067] Potential additives

[0068] In some embodiments, the agricultural formulations of the present invention may include components other than the agriculturally active ingredient, an alkyl furan ester solvent according to Formula 1, and potential co-solvents. In some embodiments, the agricultural formulations of the present invention further include one or more of a surfactant, an emulsifier, a dispersant, a humectant, an adjuvant, an antioxidant, a rheology modifier, an antifreeze agent, or a colorant.

[0069] Surfactants that can be used in the present invention can be anionic, nonionic or cationic in nature, and can be used as wetting agents, suspending agents, anti-foaming agents and defoaming agents and other functions. Anionic and nonionic surfactants are usually used in admixture. Surfactants commonly used in agricultural formulations are described in "Encyclopedia of Surfactants", Volumes I-III, Chemical Publishing Co., New York, 1980-81, and "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1998. Typical surfactants include, but are not limited to, alkylphenol-alkylene oxide addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecanol-C16 ethoxylate; quaternary amines, such as lauryl trimethyl ammonium chloride; salts of monoalkyl phosphates and dialkyl phosphates; and solid or liquid organosilicones. Examples of suitable organosilicon surfactants include commercially available polysiloxane / polyether copolymers, such as TEGOSTAB B-8462, B-8404, and B-8871 available from Evonik AG, and VORASURF available from Dow Chemical Company. TM DC-198 and DC-5043 surfactants, and NIAX L-618 and NIAX L-627 surfactants from Momentive Performance Materials.

[0070] Representative emulsifiers include, but are not limited to, anionic emulsifiers such as alkaline earth metal, alkali metal and amine salts of dodecylbenzenesulfonic acid, alkylarylsulfonic acid and alkylnaphthalenesulfonic acid, sodium dialkylsulfosuccinate, sodium diisooctylsulfosuccinate and amine salts of ether sulfates. Nonionic emulsifiers include fatty acid alkanolamides; condensation products of fatty alcohols, fatty amines, fatty acid esters and fatty acid amides with ethylene oxide and / or propylene oxide; condensation products of straight-chain or branched primary alcohols with ethylene oxide and / or propylene oxide; condensation products of straight-chain or branched secondary alcohols with ethylene oxide and / or propylene oxide; fatty esters of polyol esters, such as sorbitan fatty acid esters; condensation products of polyol ester fatty esters with ethylene oxide, such as polyoxyethylene sorbitan fatty acid esters; ethoxylated lanolin alcohols; ethoxylated lanolin acid. Cationic emulsifiers include fatty monoamine, diamine or polyamine acetates and oleates. Combined anionic and nonionic emulsifier products which can be used as premix products include, for example, TENSIOFIX B.7416, B.7438 and B.7453 and ATLOX 4851B and 4855B.

[0071] Representative dispersants include, but are not limited to, nonionic surfactants and wetting agents such as those prepared by sequentially adding propylene oxide and then ethylene oxide to propylene glycol, block copolymers of ethylene oxide and propylene oxide, and condensation products of linear alcohols with ethylene oxide and propylene oxide, such as butanol ethylene oxide or propylene oxide copolymers.

[0072] Representative humectants include, but are not limited to, propylene glycol, glycerin, and polyethylene glycol.

[0073] Representative adjuvants include, but are not limited to, dispersants, petroleum and plant-derived oils and solvents, wetting agents. Useful adjuvants in emulsifiable concentrate compositions are described in the Compendium of Herbicide Adjuvants, 9th edition, edited by Bryan Young, Dept. of Plant, Soil, and Agricultural Systems, Southern Illinois University, MC-4415, 1205 Lincoln Dr., Carbondale, IL 62901. Examples of adjuvants include, but are not limited to, alkyl polysaccharides and blends, amine ethoxylates, polyethylene glycol esters, ethoxylated alkyl aryl phosphates, paraffin oils, horticultural spray oils, methylated rapeseed oil, methylated soybean oil, refined vegetable oils, 2-ethylhexyl stearate, n-butyl oleate, propylene glycol dioleate, isopropyl myristate, and ethylene vinyl acetate terpolymers.

[0074] One of ordinary skill in the art can identify potential antioxidants, rheology modifiers, antifreeze agents, or colorants that can be used in some embodiments of agricultural formulations based on the teachings herein.

[0075] The total amount of additives in the agricultural formulations of the present invention (if present) is greater than (>) 0, or greater than or equal to (≥) 0.5, or ≥ 1, or ≥ 1.5 weight percent (wt%) of the formulation, based on the total weight of the formulation. Typically, the total amount of additives in the agricultural formulation is less than or equal to (≤) 15 wt%, or ≤ 10 wt%, or ≤ 5 wt%, or ≤ 3 wt% of the formulation, based on the total weight of the formulation. In one embodiment, the total amount of additives in the agricultural formulation is > 0 wt% to ≤ 15 wt%, or ≥ 0.5 wt% to ≤ 10 wt%, or ≥ 1 wt% to ≤ 5 wt% of the formulation, based on the total weight of the formulation.

[0076] Preparation of agricultural preparations

[0077] The agricultural formulations of the present invention can be prepared using techniques known to those of ordinary skill in the art based on the teachings herein.

[0078] In some embodiments, the agricultural formulation of the present invention can be prepared into an emulsifiable concentrate. Such emulsifiable concentrates can be prepared in a container or tank with an agitator for mixing or high shear mixing. All equipment and pipelines used are usually dry and do not contain moisture or water residues. Before producing an emulsifiable concentrate product, nitrogen can be used to flush the air in the process system. The formulation components containing agricultural active ingredients, fertilizer additives, solvents, surfactants, emulsifiers, dispersants, wetting agents, adjuvants, antioxidants or colorants are added to the processing container in sequence as a single component or in a grouped form under stirring. The components of the emulsifiable concentrate can be added in liquid, solid or molten form. The composition is mixed at a controlled temperature of generally 25 to 30°C for 1 to 2 hours or until a uniform solution is obtained. In some cases, an elevated temperature is used to form a uniform solution, for example, between 30°C and 80°C. In some cases, a GAF or similar filter can be used to filter the emulsifiable concentrate solution.

[0079] Some embodiments of the present invention will now be described in detail in the following examples.

[0080] Example

[0081] The following examples are given to illustrate the present invention and should not be construed as limiting its scope. Unless otherwise indicated, all parts and percentages are by weight.

[0082] An example of an ethyl furanate solvent Formula 1 that can be used in embodiments of the agricultural formulations of the present invention is ethyl 2-furoate ("Formula 1 Solvent A"). In the following examples, the Formula 1 Solvent A used is Ethyl 408, which is ethyl 2-furoate commercially available from xF Technologies Inc.

[0083] Example 1

[0084] The solubility of the solvent A of Formula 1 in water was measured to be 0.67 wt %. The solubility of water in the solvent A of Formula 1 was measured to be 1.44 wt %.

[0085] The solubility in water of another Formula 1 solvent, 5-methyl-2-furoate, was also measured and found to be 0.67 wt %.

[0086] Example 2

[0087] In this example, the solubility of various agricultural active ingredients in solvent A of Formula 1 is compared with their solubility in an aromatic hydrocarbon solvent. The aromatic hydrocarbon solvent used is Aromatic 150 ("aromatic hydrocarbon") from Exxon Mobil Corporation. The agricultural active ingredients used are bifenthrin, tebuconazole, chlorpyrifos, and dicamba acid.

[0088] Solubility was determined by visual observation using the following method. Agricultural active ingredients (10% to 50% by weight) and a specified solvent (90% to 50% by weight) were loaded into four milliliters of vials. The vials were capped and sealed with insulating tape. The vials were fixed in plastic containers and vibrated on a laboratory oscillator for 12 hours at laboratory ambient temperature and humidity. After 12 hours, each sample group was evaluated for the solubility of the agricultural active ingredient solid. If a uniform clear solution is observed, it is determined that complete dissolution of the agricultural active ingredient is achieved. The preparations made using Formula 1 solvent A represent some embodiments of the agricultural preparations of the present invention. The results are shown in Table 2:

[0089] Table 2

[0090]

[0091] The results show that ethyl 2-furoate provides superior solubility of tebuconazole and dicamba acid compared to aromatic hydrocarbon solvents. In addition, ethyl 2-furoate exhibits superior environmental attributes relative to Aromatic 150 (because ethyl 2-furoate is based on renewable raw materials) for use in preparing agricultural formulations.

[0092] Example 3

[0093] In this example, the solubility of various agricultural active ingredients in solvent A of Formula 1 is compared with their solubility in N,N-dialkyl fatty acid amide solvent. The N,N-dialkyl fatty acid amide solvent used is HALLCOMID M-10, which is N,N-dimethyldecylamide ("N,N-dialkyl fatty acid amide") from Stepan Company. The agricultural active ingredients used are bifenthrin, tebuconazole, chlorpyrifos, and dicamba acid.

[0094] Solubility was determined by visual observation using the following method. Agricultural active ingredients (10% to 50% by weight) and specified solvents (90% to 50% by weight) were loaded into four milliliters of vials. The vials were capped and sealed with insulating tape. The vials were fixed in plastic containers and vibrated on a laboratory oscillator for 12 hours at laboratory ambient temperature and humidity. After 12 hours, each sample group was evaluated for the solubility of the agricultural active ingredient solid. If a uniform clear solution is observed, it is determined that complete dissolution of the agricultural active ingredient is achieved. The preparations made using Formula 1 solvent A represent some embodiments of the agricultural preparations of the present invention. The results are shown in Table 3:

[0095] Table 3

[0096]

[0097] The results showed that ethyl 2-furoate provided superior solubility of dicamba acid compared to N,N-dialkyl fatty amide solvents. In addition, ethyl 2-furoate provided comparable solubility of bifenthrin and a better toxicological profile.

Claims

1. An agricultural preparation, comprising: at least one agriculturally active ingredient, the at least one agriculturally active ingredient being present in an amount of 1 wt % to up to 80 wt %, based on the total weight of the agricultural formulation; and Alkyl furan ester solvent according to Formula 1: wherein R1 is a methyl group, an ethyl group or a straight or branched alkyl group having 3 carbon atoms, and wherein the agricultural formulation comprises from 5% to at most 80% by weight of the alkyl furan ester solvent, and The agricultural active ingredient is at least one of the following: bifenthrin, tebuconazole, dicamba acid and chlorpyrifos.

2. The agricultural formulation of claim 1, further comprising less than 50% by weight of a co-solvent.

3. The agricultural formulation of claim 2, wherein the co-solvent comprises at least one of the following: an N,N-dialkyl fatty amide solvent, an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, an aromatic ketone, an alkyl ketone or a cyclic ketone solvent, a glycol ether solvent, a fatty acid ester solvent, or a combination thereof.

4. The agricultural formulation of claim 1 or claim 2, wherein the agriculturally active ingredient is soluble in at least one of N,N-dialkyl fatty amides, aromatic ketones, alkyl ketones, cyclic ketones, or aromatic hydrocarbon solvents.

5. The agricultural formulation of claim 4, comprising less than 50% by weight of an aromatic hydrocarbon solvent.

6. The agricultural formulation according to claim 4, which does not contain an aromatic hydrocarbon solvent.

7. The agricultural formulation of claim 4, comprising less than 50% by weight of an N,N-dialkyl fatty amide solvent.

8. The agricultural formulation according to claim 4, which does not contain an N,N-dialkyl fatty amide solvent.

9. The agricultural formulation of claim 4, comprising less than 50% by weight of aromatic ketone, alkyl ketone and cyclic ketone solvents.

10. The agricultural formulation according to claim 4, which is free of aromatic ketone, alkyl ketone and cyclic ketone solvents.

11. The agricultural formulation according to any one of claims 1 to 3, further comprising additives, wherein the total amount of the additives accounts for >0 to less than or equal to 15% by weight of the agricultural formulation.

12. The agricultural formulation of claim 11, wherein the agricultural formulation comprises a surfactant.

13. The agricultural formulation of claim 11, wherein the agricultural formulation comprises one or more of an emulsifier, a dispersant, a wetting agent, an antioxidant, a rheology modifier, an antifreeze agent, or a colorant.

14. The agricultural formulation of claim 11, wherein the agricultural formulation comprises an adjuvant.

15. The agricultural formulation according to any one of claims 1 to 3, wherein R1 in Formula 1 is an ethyl group.

16. The agricultural formulation according to any one of claims 1 to 3, wherein the agricultural formulation is in the form of an emulsifiable concentrate.

17. The agricultural formulation of claim 2, wherein the co-solvent comprises a seed oil solvent.

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