Oil-flowable apyrase inhibitor formulation

Abstract

The present disclosure provides a formulation comprising a first active compound having structure (I): TIFF2025542196000062.tif33165 relates to an oil-flowable formulation comprising a lipophilic solvent, a first dispersant, and a rheology modifier. The formulation comprises particles of a first active compound having a median particle size of 0.1 to 20 microns as measured by light scattering. The formulation may also include an emulsifier, a second dispersant, and / or an agriculturally active compound (e.g., an acaricide, antibacterial agent, fungicide, herbicide, insecticide, molluscicide, or nematicide, or a combination thereof). Also disclosed are agricultural compositions comprising the formulation and methods of using the same.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of the earlier filing date of U.S. Provisional Patent Application No. 63 / 476,309, filed December 20, 2022, which is incorporated herein by reference in its entirety.

[0002] The present disclosure relates to oil-flowable apyrase inhibitor formulations and methods of use thereof, particularly in the treatment of pathogen-susceptible crops. [Background technology]

[0003] Crops are plagued by a variety of pathogens worldwide. Pathogens, such as insects, mites, nematodes, weeds, and fungi, have developed numerous mechanisms to survive pesticides, for example, by sequestering, excreting, or detoxifying the pesticides. There is a need for formulations that enhance the efficacy of pesticides by blocking certain resistance mechanisms. Summary of the Invention [Means for solving the problem]

[0004] In this specification, the structure [ka] A composition is disclosed that includes a compound having the formula:

[0005] In some embodiments, the compound is present in the form of particles, e.g., particles having a volume weighted median particle size in the range of greater than 0.01 microns to 40 microns, e.g., 0.01 microns to 30 microns, 0.01 microns to 25 microns, e.g., greater than 0.01 microns to 20 microns, e.g., 0.1 microns to 5 microns, or 0.5 microns to 2 microns; in certain embodiments, the volume weighted median particle size is 1 micron. In some embodiments, the particles are present in an amount of 5% to 90% by weight, e.g., 30% to 85% by weight, or 30% to 50% by weight.

[0006] The lipophilic solvent may include mineral oil, fatty acid, vegetable or seed oil, terpene, aliphatic solvent, cyclic hydrocarbon solvent, aromatic solvent, or derivatives and / or combinations thereof. In some embodiments, the lipophilic solvent includes a fatty acid derivative. The fatty acid derivative may be selected from fatty acid esters, fatty acid dialkylamides, and combinations thereof. In some embodiments, the fatty acid derivative may include an oleic acid ester, such as methyl oleate.

[0007] In other embodiments, the lipophilic solvent comprises a paraffinic solvent, and in further embodiments, the lipophilic solvent comprises an aromatic solvent, which may include tetrahydronaphthalene, alkylated naphthalene, derivatives thereof, or combinations thereof.

[0008] The rheology modifier may include an organically modified clay, silica or hydrophobically modified silica, alumina, a polyurethane-based polymer, or a combination thereof. In some embodiments, the rheology modifier is present in an amount of 0.1 wt. % to 15 wt. %, for example, 1 wt. % to 10 wt. %.

[0009] In any embodiment, the first dispersant has a molecular weight of 1,000 to 100,000 daltons and is completely soluble in the lipophilic solvent. The first dispersant may be present in an amount of 0.1% to 20% by weight, for example, 1% to 10% by weight.

[0010] The first dispersant is an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof. In some embodiments, the first dispersant is an anionic dispersant. In other embodiments, the first dispersant is a non-ionic dispersant. In some embodiments, the first dispersant is selected from a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof. In certain embodiments, the first dispersant is a copolymer, and may be a random or statistical copolymer, a block copolymer, a comb block copolymer, or a combination thereof.

[0011] In some embodiments, the composition further comprises an emulsifier and a second dispersing agent. The emulsifier may be an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, a zwitterionic surfactant, or a combination thereof, and / or may have a molecular weight of 150 Daltons to 1,200 Daltons.

[0012] In some embodiments, the second dispersant can have a molecular weight of 1,000 Daltons to 100,000 Daltons and / or is water soluble.

[0013] In some embodiments, the composition does not contain more than 0.1% by weight of compounds containing primary amines, secondary amines, and / or tertiary amines.

[0014] In some embodiments, the composition does not contain more than 0.1% by weight of quaternary ammonium compounds.

[0015] In either embodiment, the composition may further comprise an agriculturally active compound.

[0016] Also disclosed herein are embodiments of agricultural compositions that include water and / or a lipophilic solvent and a composition disclosed herein, e.g., 0.01% to 10% by weight of the composition. Methods of using the agricultural compositions are also disclosed. The methods can include applying the agricultural composition to a plant, a plant part, a seed, soil in which a plant is growing or will grow, or soil in which a seed has been or will be sown.

[0017] Also disclosed are methods for controlling or preventing fungal growth using the disclosed compositions or agricultural compositions thereof.

[0018] The foregoing and other objects, features, and advantages of the present invention will become more apparent from the following detailed description. DETAILED DESCRIPTION OF THE INVENTION

[0019] I. Terminology The following explanations of terms and methods are provided to more fully describe the present disclosure and to guide those skilled in the art in practicing the present disclosure. The singular forms "a," "an," and "the" refer to one or more, unless the context clearly dictates otherwise. The term "or" refers to any single element of listed alternative elements or a combination of two or more elements, unless the context clearly dictates otherwise. As used herein, "comprises" means "includes." Thus, "including A or B" means "including A, B, or A and B," excluding additional elements. All references cited herein, including patents and patent applications, are incorporated by reference in their entirety unless otherwise specified.

[0020] Unless otherwise indicated, all numbers expressing amounts of ingredients, molecular weights, percentages, temperatures, times, and the like used in the specification or claims should be understood to be modified by the term "about." Thus, unless implicitly or explicitly indicated otherwise, the numerical parameters given are approximations and may depend on the desired properties sought and / or the limits of detection under standard testing conditions / methods. When directly and explicitly distinguishing an embodiment from the prior art discussed, the numbers of the embodiments are not approximations unless the word "about" is explicitly recited.

[0021] Unless otherwise explained, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of this disclosure, suitable methods and materials are described below. The materials, methods, and examples are illustrative only and are not intended to be limiting.

[0022] "Administering" refers to any suitable mode of administration for controlling pathogens, such as fungal pathogens, and includes treatment of existing crops, produce, seeds, soil, or combinations thereof.

[0023] "In combination with" refers to the administration of the compounds either simultaneously in a single administration, or sequentially in two or more different administrations that may be separated in any way, time, place, or manner.

[0024] "Control," with respect to a pathogen, such as a fungal pathogen, means blocking, inhibiting, and / or eradicating the pathogen and / or preventing the pathogen from damaging the crop. In one embodiment, control refers to reducing one or more pathogens, such as fungi, to undetectable levels, or reducing or suppressing the pathogen to an acceptable level as determined by one skilled in the art (e.g., a crop grower). Determining an acceptable level of pathogen reduction is based on numerous factors, including the crop, the pathogen, the severity of the pathogen, use limitations, economic thresholds, and other factors known to one skilled in the art.

[0025] As used herein, the terms "enhancer" and "potentiator" refer to a compound(s) disclosed herein that enhances the effectiveness of a pesticide. Without being limited by theory, the enhancer compounds disclosed herein may function by blocking one or more pathways by which pathogens, such as fungal pathogens, avoid the toxicity of pesticides, such as by detoxifying, sequestering, or transporting them. In certain embodiments, the compounds inhibit the activity of the enzyme apyrase, which enhances, potentiates, or synergizes pesticides, such as acaricides, antimicrobials, fungicides, herbicides, insecticides, molluscicides, and / or nematicides. For example, when an enhancer or potentiator is used in conjunction with a fungicide, the combination of the potentiator and fungicide enhances the fungicidal effect of the fungicide, and / or as a result of the activity of the potentiator, fungi that have previously been resistant to the fungicide become susceptible to the fungicide. In most cases, these enhancers or potentiators do not themselves inhibit the growth of the pathogen, such as a fungus, itself, and do not have a deleterious effect on organisms that are (or may be) infected with the pathogen.

[0026] As used herein, the term "treatment" refers to a method used to administer or apply an effective amount of the disclosed compounds or formulations thereof to a target area of ​​a field and / or plant. Treatment methods can include, but are not limited to, aerosol spraying, pressure spraying, direct watering, chemical solution irrigation, spraying, and immersion. Target areas of a plant can include, but are not limited to, leaves, roots, stems, buds, flowers, fruits, plant seeds, and plant bulbs, including bulbs, corms, rhizomes, tubers, root nodules, and rhizophores. Treatment can include methods in which a plant is treated in one area (e.g., the root zone or foliage) and another area of ​​the plant is protected (e.g., foliage is protected when the disclosed compounds are applied to the shoots when applied to the root zone or foliage).

[0027] As used herein, the terms "oil flowable," "oil-mixed flowable," "oil-mixed suspension," or "OF" refer to a liquid formulation containing a stable suspension of an active ingredient in oil. Oil-flowable formulations can be stored and provided to the market and / or end users without further processing. In actual applications, oil-flowable formulations are prepared for application by end users. Typically, oil-flowable formulations are mixed with water and / or lipophilic solvents in the end user's spray tank until appropriately diluted for the specific application. Dilution may vary depending on the crop, pathogen, time of year, geography, local regulations, and degree of infestation, among other factors. Once appropriately diluted, the formulation can be applied, such as by spraying.

[0028] II. Formulation A common goal for agricultural product formulators is to maximize the biological activity of active ingredients. This is particularly difficult in suspension formulations, because the solid state of the active ingredient tends to limit its bioavailability. However, it is generally not possible to predict whether a particular active ingredient will have good biological activity when delivered as a suspension. Without being limited by theoretical understanding, factors that can determine biological activity include aqueous solubility (including how it varies with temperature, salinity, and pH at the application site), solubility in hydrophobic domains (including within the waxy leaf cuticle and any micellar surfactant domains), crystal lattice energy, the density of active ingredient crystals and their associated tendency to sediment, the existence of crystalline polymorphs and metastable states, diffusivity in water, the ability of the active ingredient to diffuse through the plant cuticle, the location of the active ingredient's site of action, and the required concentration of the active ingredient at that site. To overcome the limitations of biological activity, a large number of modifications may be discoverable by the formulator, and many of these modifications have interdependent effects (meaning that testing each of them separately does not adequately inform about the consequences of altering each simultaneously), making it impractical to explore the entire experimental space.

[0029] Among the formulations tested during the work described in this disclosure, the inventors discovered that oil-flowable formulations of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally exhibited poor biological activity. Furthermore, they discovered that controlling particle size within a specific size range significantly improved the biological activity of formulations containing the required ingredients described herein.

[0030] A general requirement for agricultural product formulators is to achieve acceptable stability, both in terms of chemical stability (meaning that no significant chemical degradation of the active ingredient occurs) and physical stability (meaning that the product remains similar to the product at the time of manufacture in commonly available product containers stored under conditions commonly found in the supply chain, and that the product is suitable and convenient for use by the end user). Whether a particular active ingredient is susceptible to chemical degradation is unpredictable due to the large number of factors that can determine its behavior. These include the solubility of the active ingredient in any liquid phase present (including the hydrophobic phase of any surfactant micellar structure), the presence in the liquid phase of chemical species that can catalyze degradation, any tendency of the active ingredient to undergo autocatalysis, thereby accelerating further reactions of degradation products, the presence of chemical bonds within the active ingredient that are susceptible to cleavage, and the effect of neighboring groups on their susceptibility. Physical stability also must be evaluated empirically, but it is known in the art that certain small-scale laboratory tests can often adequately represent larger-scale behavior in commercial applications.

[0031] Among the formulations tested during the work described in this disclosure, the inventors discovered that an aqueous suspension of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide had unacceptable chemical stability. However, the oil-flowable formulations described herein and containing the required ingredients of this disclosure were found to have sufficient physical stability and remain suitable for use when subjected to stress testing at elevated temperatures, including temperatures that commercial products may experience during shipping, storage, and use.

[0032] As used herein, the structure [ka] An oil-flowable formulation is disclosed that includes a first active compound having the formula:

[0033] In some embodiments, the oil-flowable formulation further comprises a lipophilic solvent, a first dispersant, and a rheology modifier. In some embodiments, the oil-flowable formulation is an oil admixture suitable for dilution, such as by an end user.

[0034] In some embodiments, the first active compound is present as a suspension in the formulation. The suspended particles have a volume-weighted median particle size, as measured by light scattering, in the range of greater than 0.01 microns to 40 microns, e.g., 0.01 microns to 30 microns, 0.01 microns to 25 microns, e.g., greater than 0.01 microns to 20 microns, 0.01 microns to 15 microns, 0.01 microns to 10 microns, e.g., 0.1 microns to 5 microns, or 0.5 microns to 2 microns. In certain embodiments, the volume-weighted median particle size is 1 micron. In certain other embodiments, the volume-weighted median particle size is 7.0 microns. In yet other embodiments, the volume-weighted median particle size is 15 microns. Furthermore, when the formulation includes additional suspending substances, such as those disclosed herein, any such additional suspending substances may also have a particle size, as measured by light scattering, as disclosed above for the first active compound.

[0035] A. First Active Compound The oil-flowable formulations include a first active compound, (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, in an amount sufficient to enhance the effectiveness of one or more agriculturally active compounds that may be applied in combination with the first active compound when diluted for use. In some embodiments, the oil-flowable formulations include 5% to 90% by weight of the first active compound, e.g., 10% to 90%, 20% to 90%, 30% to 85%, 30% to 75%, 30% to 65%, 30% to 50%, or 30% to 40% by weight of the first active compound.

[0036] B. Lipophilic solvent In some embodiments, the lipophilic solvent is or includes a mineral oil, a fatty acid, a vegetable or seed oil, a terpene, an aliphatic solvent, a cyclic hydrocarbon solvent, an aromatic solvent, or a derivative and / or combination thereof. In certain embodiments, the lipophilic solvent is or includes a fatty acid derivative, such as methyl oleate, methyl linoleate, or a combination thereof, such as Steposol® ME. In some embodiments, the lipophilic solvent is or includes a paraffinic solvent, such as Exxsol™ D80, Exxsol™ D110, or Exxsol™ D130 paraffinic solvent. In some embodiments, the lipophilic solvent is or includes an aromatic solvent, such as a Solvesso™ aromatic solvent, such as Solvesso™ 200ND or Solvesso™ 150ND. In some embodiments, the lipophilic solvent includes an aromatic solvent and is or includes tetrahydronaphthalene, alkylated naphthalene, derivatives thereof, and / or combinations thereof.

[0037] In some embodiments, the lipophilic solvent is selected so that the first active compound is substantially insoluble in the lipophilic solvent. In some embodiments, the first active compound has a solubility in the lipophilic solvent under ambient conditions of less than 2% by weight, for example, a solubility in the lipophilic solvent of 0-2% by weight, 0-1% by weight, or 0-0.1% by weight. Those skilled in the art will understand that the solubility of a compound in an organic solvent can be determined by conventional methods known to those skilled in the art.

[0038] C. Rheology Modifiers In some embodiments, the rheology modifier is or includes an organically modified clay, silica or hydrophobically modified silica, alumina, a polyurethane-based polymer, or a combination thereof. In some embodiments, the rheology modifier is or includes an organically modified clay, such as a hydrated aluminum magnesium silicate, e.g., Attagel® 50. In some embodiments, the rheology modifier is or includes a hydrophobically modified ethoxylated urethane copolymer, e.g., Borchi® Gel 0434.

[0039] The rheology modifier is present in an amount suitable to provide a desired property, such as a particular viscosity, hi some embodiments, the rheology modifier is present in the formulation in an amount of 0.1% to 15% by weight, e.g., 1% to 10% by weight.

[0040] D. First Dispersant The first dispersant may have a molecular weight of 1,000 Daltons to 100,000 Daltons or more. In some embodiments, the first dispersant is completely soluble in the lipophilic solvent. In some embodiments, the first dispersant is or includes a copolymer or homopolymer, or a combination thereof. The copolymer may be a random or statistical copolymer, a block copolymer, a comb block copolymer, or a combination thereof. Exemplary first dispersants include, but are not limited to, polyvinylpyrrolidinone; a random copolymer of a combination of vinylpyrrolidinone, stearyl methacrylate, lauryl methacrylate, and / or butyl methacrylate; a block copolymer of ethylene oxide and propylene oxide; or a combination thereof.

[0041] The first dispersing agent may be present in the formulation in an amount of from 0.1% to 20% by weight, for example from 1% to 10% by weight.

[0042] E. Emulsifiers Optionally, the oil-flowable formulation further comprises an emulsifier. The emulsifier can be an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, a zwitterionic surfactant, or a combination thereof. In some embodiments, the surfactant is an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof. In any embodiment, the emulsifier can have a molecular weight of 150 daltons to 1,200 daltons.

[0043] In any embodiment, the anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate. The anionic surfactant may be an ester of an alcohol, an alcohol alkoxylate (e.g., an alcohol ethoxylate and / or an alcohol propoxylate), a tristyrylphenol ethoxylate, a fatty acid, a natural oil, or a combination thereof. In other embodiments, the anionic surfactant may be a salt of a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate, such as a calcium salt, a sodium salt, a potassium salt, a lithium salt, an organic amine salt, or an ammonium salt.

[0044] In certain embodiments, the organic amine salt is a salt of isopropylamine, butylamine, ethylamine, diethylamine, triethylamine, diethanolamine, triethanolamine, methylamine, ethylenediamine, or a combination thereof.

[0045] In certain embodiments, the anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate ester of an alcohol, alcohol alkoxylate, tristyrylphenol ethoxylate, fatty acid, or natural oil, or any combination thereof. An exemplary anionic surfactant is Agnique™ ABS60C-EH, which contains calcium dodecylbenzenesulfonate.

[0046] The cationic surfactant can be an ethoxylated amine, for example, an ethoxylated amine of a natural oil, an alcohol, a fatty acid, or a combination thereof.

[0047] In some embodiments, the formulation does not contain more than 0.1 wt. % of compounds containing primary amines, secondary amines, and / or tertiary amines, e.g., zero to 0.1 wt. % of such compounds, or zero wt. % of such compounds. In some embodiments, the formulation does not contain more than 0.1 wt. % of compounds containing quaternary ammonium compounds, e.g., zero to 0.1 wt. % of such compounds, or zero wt. % of such compounds. In some such embodiments, the anionic surfactant may be a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate salt, e.g., a calcium, sodium, potassium, or lithium salt.

[0048] The nonionic surfactant may be an alkoxylate of an alcohol, a natural oil, a fatty alcohol, or a combination thereof, such as an ethoxylate and / or propoxylate of an alcohol, a natural oil, a fatty alcohol, or a combination thereof. An exemplary nonionic surfactant is Plurafac® LF700, an alkoxylated fatty alcohol.

[0049] The quaternary ammonium surfactant can include at least one chain having at least 6 carbon atoms, e.g., 6 to 20 carbon atoms, or 6 to 12 carbon atoms, attached to a quaternary ammonium head group.

[0050] Also, in some embodiments, the zwitterionic surfactant comprises a positively charged group, e.g., a quaternary ammonium group, and a negatively charged group, e.g., a carboxylic acid moiety, a sulfonic acid moiety, or a phosphate moiety. An example of a zwitterionic surfactant is cocamidopropyl betaine.

[0051] In other embodiments, the surfactant is a non-ionic surfactant and may be selected from alkoxylates of alcohols, natural oils, or combinations thereof.

[0052] With particular reference to the surfactants disclosed herein, one of ordinary skill in the art will understand that the alkoxylate group (e.g., ethoxylate or propoxylate) can contain one or more alkoxy moieties (i.e., can be polyalkoxylated), such as from 1 to 200 or more alkoxy moieties, and in some embodiments, the alkoxylate group contains from 2 to 200 alkoxy groups, e.g., from 4 to 200, or from 4 to 150 alkoxy groups.

[0053] F. Secondary Dispersant Optionally, the oil-flowable formulation further comprises a second dispersant. The second dispersant is an anionic dispersant, a cationic dispersant, a nonionic dispersant, or a combination thereof. The second dispersant may have a molecular weight of 1,000 to 100,000 daltons. In some embodiments, the second dispersant is water-soluble. In some embodiments, the second dispersant is or comprises a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof. In some embodiments, the second dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyvinyl sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinate, vinylpyrrolidone / vinyl caprolactam, polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohol, polyethoxylated diamine, naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, ethoxylated lignosulfonate, or a combination thereof.

[0054] In certain embodiments, the second dispersant is an anionic dispersant.

[0055] In other embodiments, the second dispersant is a non-ionic dispersant.

[0056] In some embodiments, the oil-flowable formulation comprises both an emulsifier and a second dispersing agent.

[0057] III. Agriculturally Active Compounds The disclosed formulation can further comprise agriculturally active compounds.In addition, or alternatively, the formulation can be used in combination with one or more agriculturally active compounds as a part of agricultural composition, which is typically applied to crops, the seeds that can be sown to produce crops, harvested produce, and / or the soil that crops are planted in or can be planted or sown in.The agricultural composition can be at least partially formed by diluting the disclosed formulation with suitable solvent or solvent mixture, for example, water and / or lipophilic solvent as described above.

[0058] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of various pesticides, including fungicides, antivirals, antibacterials, herbicides, insecticides / acaricides, molluscicides, nematicides, soil pesticides, plant control agents, synergists, fertilizers and soil amendments, such as fungicides, repellents, herbicides, insecticides, molluscicides, nematicides, or combinations thereof.

[0059] In one embodiment, the formulations of the present disclosure are useful for enhancing the germicidal effect of various germicides. Germicidal agents for use with the disclosed formulations are well known to those of skill in the art and include, but are not limited to, those listed by class in Table 1: [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8]

[0060] Fungicides are more extensively cataloged by the Fungicide Resistance Task Force (FRAC) in the FRAC Code List 2022, reproduced in Appendix 1, which is incorporated herein by reference in its entirety.

[0061] In one embodiment, the disclosed formulations are used in combination with one or more compounds from a family or group set forth in Table 1, Appendix 1, or both. In certain embodiments, the formulations are used in combination with one or more fungicides listed in column 1 of Table 1.

[0062] In certain embodiments, the disclosed formulations include any of the following: cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole, metconazole, ipconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, morpholine, cyflufenamid, metrafenone, pyriophenone, strobilurin, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, lime sulfur, ethylene bisdithiocarbamate, aromatic hydrocarbons, phthalimide, guaiaconazole ... In some embodiments, the fungicides may be used in combination with one or more of the fungicides selected from benzimidazoles, including imidazoles and triazoles such as cinnamic acid, polyoxins, furazinam, and thiazolidine, dicarboximides, phenylpyrroles, anilinopyrimidines, hydroxyanilides, carboxamides, phenylamides, phosphonates, cinnamic acids, oxysterol binding protein inhibitors (OSBPIs), triazole carboxamides, cymoxanil, carbamates, benzamides, demethylation-inhibiting piperazines, demethylation-inhibiting pyrimidines, and demethylation-inhibiting azoles.

[0063] Specific fungicides that may be potentiated by administration of an apyrase inhibitor when used in combination with the formulations disclosed according to the methods herein include copper, such as copper octoate, copper hydroxide, copper sulfate, myclobutanil, propiconazole, tebuconazole, epoxiconazole, difenoconazole, triticonazole, and prothioconazole.

[0064] In one embodiment, combined treatment with a selected fungicide and the disclosed formulations provides synergistic fungicidal activity against plant pathogenic fungi.

[0065] In one embodiment, the present disclosure provides compositions and methods for treating plants or plant seeds infected or at risk of infection with fungal pathogens. In one embodiment, the disclosed composition comprises a fungicide formulation, a disclosed formulation, and a phytologically acceptable carrier. In another embodiment, the fungicide and formulation are administered in separate compositions. In a further embodiment, agricultural or horticultural fungicides are used in combination with other compounds in addition to the disclosed formulation. Such other compounds may be administered in the same or separate compositions as the fungicide and / or formulation. Examples of other ingredients include known carriers used to formulate the formulation. Additional examples include conventionally known herbicides, insecticides / acaricides, nematicides, soil pesticides, plant control agents, synergists, fertilizers, soil conditioners, and animal feeds. In one embodiment, the inclusion of such other ingredients provides a synergistic effect on crop growth.

[0066] In one embodiment, the disclosed formulations are used to enhance the effectiveness of herbicides. Exemplary herbicides for use in combination with the formulations are known to those of skill in the art and include, but are not limited to, those listed in Appendix 2. By way of example, suitable herbicides for use in combination with the disclosed formulations include inhibitors of acetyl-CoA synthetase, inhibitors of acetolactate synthesis, inhibitors of microtubule polymerization, inhibitors of microtubule organization, auxin mimetics, photosynthesis inhibitors, deoxy-D-xylulose phosphate synthase inhibitors, enolpyruvylshikimate phosphate synthase inhibitors, phytoene desaturase inhibitors, glutamine synthetase inhibitors, dihydropteroate synthesis inhibitors, protoporphyrinogen oxidase inhibitors, cellulose synthesis inhibitors, uncouplers, hydroxyphenylpyruvate dioxygenase inhibitors, fatty acid thioesterase inhibitors, serine-threonine protein phosphatase inhibitors, solanesyl diphosphate synthase inhibitors, inhibitors of very long chain fatty acid synthesis, homogentisate solanesyltransferase inhibitors, and / or lycopene cyclase inhibitors.

[0067] In one embodiment, the disclosed formulations are used to enhance the effectiveness of pesticides. Exemplary pesticides for use in combination with the disclosed formulations are known to those of skill in the art and include, without limitation, those listed in Appendix 3.

[0068] IV. How to Use the Formulation Embodiments of methods of using the disclosed formulations include diluting the formulation with a suitable diluent, such as water and / or a lipophilic solvent, to form an agronomic composition suitable for application to a plant, a plant part, a seed, the soil in which the plant is growing or will grow, or the soil in which the seed has been or will be sown. The method may further include applying the agronomic composition to the plant, a plant part, the soil in which the plant is growing or will be grown, or the soil in which the seed has been or will be sown.

[0069] In some embodiments, the disclosed formulations include one or more agriculturally active compounds, and the agricultural composition is formed by diluting the formulation with a suitable solvent, such as water and / or a lipophilic solvent, to a concentration suitable for agricultural use. Optionally, one or more additional agriculturally active compounds can be added before, during, and / or after diluting the formulation.

[0070] In other embodiments, the formulation does not include an agriculturally active compound, and the agricultural composition is formed by diluting the formulation with a suitable solvent, such as water and / or a lipophilic solvent, to a concentration suitable for agricultural use. In such embodiments, forming the agricultural composition may further include adding one or more agriculturally active compounds to the water and / or lipophilic solvent before the formulation is added, at the same time as the formulation is diluted with water and / or lipophilic solvent, and / or to the diluted mixture containing the formulation later.

[0071] In certain non-limiting embodiments, the disclosed formulations are diluted for agricultural use in an amount sufficient to provide 0.01 to 80% by weight of the first active compound in the final composition, or 25% to 55%, e.g., 30% to 50%, 35% to 45%, e.g., 0.01, 0.05, 0.1, 0.5, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.5, 3.0, 4.0, 5.0, 7.5, 10, 20, 30, 40, 50, 55, 60, or 80% by weight of the first active compound in the final composition. In one embodiment, the first active compound is provided in the final diluted composition in a volume ratio of 0.01 to 50%, e.g., 15% to 50%, 20% to 45%, 25% to 40%, e.g., 0.01, 0.05, 0.1, 0.5, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.5, 3.0, 4.0, 5.0, 7.5, 10, 15, 20, 30, 40 or 50%.

[0072] In some embodiments, the agriculturally active compound(s) are present in the agricultural composition at a concentration that is less than the concentration of the agriculturally active compound(s) recommended for use in the absence of a formulation disclosed herein, for example, in the absence of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0073] In some embodiments, a method of making an agricultural composition includes adding a formulation disclosed herein to water and / or a lipophilic solvent in an amount sufficient to enhance the agriculturally active compound(s), and adding the agriculturally active compound(s) in an amount sufficient to achieve a concentration in the agricultural composition that is less than the concentration recommended for use in the absence of the disclosed formulation, e.g., in the absence of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide. One of skill in the art will understand that the disclosed formulation and agriculturally active compound may be added sequentially in any order or substantially simultaneously to the water and / or lipophilic solvent to form the agricultural composition.

[0074] In any embodiment, the one or more agriculturally active compounds can be an agricultural or horticultural pesticide disclosed herein, such as an acaricide, antimicrobial, fungicide, herbicide, insecticide, molluscicide, or nematicide, or a combination thereof. In some embodiments, the method is for controlling or preventing fungal growth.

[0075] Crops that can be treated include, but are not limited to, those affected by various pathogens, including bacteria, viruses, fungal pathogens, mites, nematodes, mollusks, weeds, or other pests, as known to those skilled in the art of agriculture. By way of example, such agricultural and horticultural crops that can be treated according to the present disclosure include, for example, cereals; vegetables; root vegetables; potatoes; fruit trees, such as banana trees, tea trees, coffee trees, or cocoa trees; grasses; turf; or cotton, including their harvests, whether genetically modified or not.

[0076] Agronomic compositions containing the disclosed formulations can be applied to plant parts such as leaves, stems, stems, flowers, buds, fruits, seeds, shoots, roots, tubers, tuberous roots, shoots, or stumps. The formulations can also be applied to improved varieties, cultivars, and mutant, hybrid, and genetically modified embodiments of these plants.

[0077] Agronomic compositions containing the disclosed formulations can be used as seed treatments, foliage applications, soil applications, or water applications to control a variety of diseases occurring in agricultural or horticultural crops, including flowers, turf, and pasture grasses.

[0078] Agricultural compositions containing the disclosed formulations are useful for enhancing the effectiveness of antimicrobial agents, for example, the disclosed formulations can be used in combination with antimicrobial agents to combat bacterial and viral infections.

[0079] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of herbicides. For example, the disclosed formulations can be used in combination with one or more herbicides to control weeds or other unwanted vegetation.

[0080] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of insecticides, for example, the disclosed formulations can be used in combination with one or more insecticides to control insect infestations.

[0081] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of acaricides or miticides. For example, the disclosed formulations can be used in combination with one or more acaricides to control mites.

[0082] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of molluscicides. For example, the disclosed formulations can be used in combination with one or more molluscicides to prevent damage to crops by slugs or snails.

[0083] Embodiments of the disclosed formulations are useful for enhancing the effectiveness of nematicides, for example, the disclosed formulations can be used in combination with one or more nematicides to prevent nematode damage to crops.

[0084] Embodiments of the disclosed formulations are particularly useful for enhancing the effectiveness of fungicides against fungal pathogens of plants. Examples of pathogens that may be treated according to the present disclosure include, but are not limited to, Botrytis cinerea, Colletotrichum graminicola, Fusarium oxysporum, Sclerotiana sclerotiorum, Verticillium dahlia, Mycospharella gramincola, and Sphacelotheca reliana.

[0085] Botrytis cinerea is an airborne plant pathogen with a biocidal lifestyle that infects over 200 crop hosts worldwide. The fungus primarily attacks dicotyledonous plant species, including important protein, oil, fiber, and horticultural crops, grapes, and strawberries; Botrytis also causes soft rot of fruits and vegetables during storage, transport, and marketing. Many classes of fungicides have been unable to control Botrytis cinerea due to its genetic plasticity.

[0086] The genus Colletotrichum contains approximately 600 species that attack over 3,200 species of monocotyledonous and dicotyledonous plants. Colletotrichum graminicola primarily infects corn (Zea mays), causing annual losses of approximately $1 billion in the United States alone (Connell et al., 2012).

[0087] Banana wilt disease, caused by the soil-borne pathogen Fusarium oxysporum f.sp. cubense, is a major threat to banana production worldwide. Currently, no fungicides are available to effectively control the disease once plants are infected (Peng J et al., 2014).

[0088] The mildew fungus Sclerotinia sclerotiorum is known to infect over 400 host species and is considered one of the most prolific plant pathogens. The majority of crop species affected are dicotyledons, as well as several agriculturally important monocotyledons. Some important crops affected by S. sclerotiorum include legumes (soybeans), most vegetables, stone fruits, and tobacco.

[0089] The ascomycete Verticillium dahliae is a soil-borne fungal plant pathogen that causes vascular wilt disease in a wide range of dicotyledonous host species. V. dahliae can cause severe yield and quality losses in cotton and other important crops, such as vegetables, fiber, fruit, nuts, trees, and ornamentals.

[0090] The ascomycete fungus Mycospharella grammingola (anamorph: Septoria tritici) is one of the most important foliar diseases of wheat leaves and occurs wherever wheat is grown. Yield losses due to this disease range from 25% to 50%, and are particularly high in Europe, the Mediterranean region, and East Africa. Infection by M. gramincola is initiated by airborne ascospores produced in residues from the previous year's crop. Primary infection usually occurs after seedling emergence in spring or autumn. Mature disease is characterized by necrotic lesions on the leaves and stems of infected plants.

[0091] The basidiomycete fungus Sphacelotheca reliana infects maize (Zea mays) systemically and causes head smut. Yield losses due to the disease are variable and directly depend on the incidence of the disease. The fungus overwinters as diploid teliospores in crop debris or soil. Floral structures transform into sporangia containing powdery teliospore masses, similar to the galls of common smut.

[0092] Examples of crops that can be treated and plant diseases (pathogens) that can be controlled using the compounds and compositions of the present disclosure include, but are not limited to:

[0093] Sugar beet: Cercospora beticola, Aphanomyces cochlioides, root rot (Thanaphorus cucumeris), leaf rot (Thanaphorus cucumeris), etc.

[0094] Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsii, Mycosphaerella berkeleyi, etc.

[0095] Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), stem blight (Mycosphaerella melonis), wilt (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), scab (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), damping-off disease (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial spot (Pseudomonas syringae pv. Lechrymans), etc.

[0096] Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), Verticillium wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), early blight (Alternaria solani), leaf mold (Pseudocercospora fuligena), etc.

[0097] Eggplant: Gray mold (Botrytis cinerea), black rot (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), leaf mold (Mycovellosiella nattrassii), Sclerotinia rot (Sclerotinia sclerotiorum), Verticillium wilt (Verticillium dahlia), Mycosphaerella blight (Phomopsis vexans), etc.

[0098] Strawberries: Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), Phytophthora cactorum, soft rot (Rhizopus stolonifer), fusarium wilt (Fusarium) oxysporum), verticillium wilt (Verticillium dahlia), etc.

[0099] Onion: Neck rot (Botrytis allii), gray mold (Botrytis cinerea), leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor), Phytophthora porn, etc.

[0100] Cabbage: Clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. Campestris), bacterial black spot (Pseudomonas syringae pv. Maculicola, Ps pv. Alisalensis), downy mildew (Peronospora parasitica), sclerotinia sclerotiorum, black spot (Alternaria brassicicola), gray mold (Botrytis cinerea), etc.

[0101] Common beans: Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc.

[0102] Apple: Powdery mildew (Podosphaera leucotricha), red mold (Venturia inaequalis), Monilinia disease (Monilinia mali), black spot (Mycosphaerella pomi), Valla rot (Valsa mali), Alternaria blotch (Alternaria mali), rust (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), leaf rot (Diplocarpon mali), fly spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), gray mold (Botrytis cinerea), etc.

[0103] Apricot: Red mold (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), etc.

[0104] Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), etc.

[0105] Peaches: Brown rot (Monilinia fructicola), red mold disease (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), bacterial bore (Xanthomonas campestris pv. Pruni), etc.

[0106] Almonds: Brown rot (Monilinia taxa), leaf spot (Stigmina carpophila), red mold (Cladosporium carpophilum), red leaf spot (Polystigma rubrum), alternaria blotch (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc.

[0107] Yellow peach: Brown rot (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Monilinia kusanoi disease (Monilinia kusanoi), etc.

[0108] Grapes: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), ripening rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), anthracnose (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white spot (Coniella castaneicola), rust (Phakopsora ampelopsidis), etc.

[0109] Pear: Red mold disease (Venturia nashicola), rust disease (Gymnosporangium asiaticum), black spot disease (Alternaria kikuchiana), ring rot disease (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), Cytospora canker disease (Phomopsis fukushii), brown spot disease (Stempphylium vesicarium), anthracnose (Glomerella cingulata), etc.

[0110] Tea: Ring spot disease (Pestalotiopsis longiseta, P. theae), anthracnose disease (Colletotrichum theae-sinensis), net cake disease (Exobasidium reticulatum), etc.

[0111] Citrus: Red mold (Elsinoe fawcettii), blue mold (Penicillium italicum), common green mold (Penicillium digitatum), gray mold (Botrytis cinerea), melanose disease (Diaporthe citri), canker disease (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), etc.

[0112] Wheat: Powdery mildew (Blumereria graminis f.sp. Tritici), head rot (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), pink snow rot (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf scorch (Septoria tritici), leaf spot (Leptosphaeria nodorum), small snow rot (Typhula incarnata), large snow rot (Myriosclerotinia borealis), damping-off (Gaeumannomyces graminis), ergot (Claviceps purpurea), smut (Tilletia caries), pungent slump (Telletia caries), naked smut (Ustilago nuda), etc.

[0113] Barley: leaf spot disease (Pyrenophora graminea), net spot disease (Pyrenophora teres), leaf blight (Rhynchosporium secalis), smut disease (Ustilago tritici, U. nuda), etc.

[0114] Rice: Blast (Pyricularia oryzae), sheath rot (Rhizoctonia solani), bacnae (Gibberella fujikuroi), brown spot (Cochliobolus miyabeanus), damping-off (Pythium graminicola), bacterial leaf blight (Xanthomonas oryzae), bacterial seedling damping-off (Burkholderia plantarii), brown stripe (Acidovorax avenae), bacterial grain rot (Burkholderia glumae), Cercospora leaf spot (Cercospora oryzae), false blast (Ustilaginoidea virens), rice brown spot (Alternaria alternata, Curvularia intermedia), rice grain discoloration (Alternaria padwickii), pink rice grain discoloration (Epicoccum purpurascens), etc.

[0115] Tobacco: Sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum), Phytophthora rot (Phytophthora nicotianae), etc.

[0116] Tulips: Gray mold (Botrytis cinerea), etc.

[0117] Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia rot (Sclerotinia sclerotiorum), etc.

[0118] Bentgrass: Snow mold (Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blight (Pyricularia sp.), Pythium wilt (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc.

[0119] Orchard grass: Powdery mildew (Erysiphe graminis), etc.

[0120] Soybean: Purple stain disease (Cercospora kikuchii), downy mildew (Peronospora manshurica), Phytophthora rot (Phytophthora sojae), rust (Phakopsora pachyrhizi), Sclerotinia rot (Sclerotinia sclerotiorum), anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), Sphaceloma scab (Elsinoe glycines), melanose (Diaporthe phaseolorum var. sojae), etc.

[0121] Potato: phytophthora infestans, early blight (Alternaria solani), scarf disease (Thanaphorus cucumeris), Verticillium wilt (Verticillium albo-atrum, V. dahlia, V. nigrescens, etc.).

[0122] Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc.

[0123] Rapeseed: Sclerotinia rot (Sclerotinia sclerotiorum), root rot (Phoma lingam), black spot (Alternaria brassicae), etc.

[0124] Coffee: Rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), leaf spot (Cercospora coffeicola), etc.

[0125] Sugarcane: Brown rust (Puccinia melanocephala), etc.

[0126] Corn: Zonate spot (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), Smit disease (Ustilago maydis), brown spot (Cochliobolus heterostrophus), northern leaf blight (Setosphaeria turcica), etc.

[0127] Cotton: Seedling damping-off (Pythium sp.), rust (Phakopsora gossypii), sour rot (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.

[0128] V. Preparation of the Formulation The disclosed formulations can be made by methods known to those skilled in the art. In some embodiments, the method includes providing a first active compound, a lipophilic solvent, a dispersant, and a rheology modifier, and forming a formulation. Optionally, an emulsifier, a second dispersant, and / or an agriculturally active compound may be added. In some embodiments, the first active compound is first ground to a desired particle size, such as a median particle size of less than 2 microns, by, for example, mixing with beads, and then used to form the formulation. In some embodiments, the ground first active compound is added to a mixture containing the lipophilic solvent, the first dispersant, and the rheology modifier. In other embodiments, the ground first active compound is added to one or more of the lipophilic solvent, the first dispersant, and the rheology modifier, and the remaining ingredients are added subsequently or simultaneously.

[0129] In either embodiment, optional ingredients, such as an emulsifier and / or a secondary dispersing agent, and any agriculturally active compound(s), can be added at any suitable stage during formulation formation.

[0130] In other embodiments, the first active compound is added to one or more of the lipophilic solvent, the first dispersing agent, and the rheology modifier, and then milled to the desired particle size, such as by stirring with beads, before adding the remaining ingredients. If an optional emulsifier and / or second dispersing agent is required, they can be added before, after, or during milling of the first active. Similarly, any agriculturally active compound(s) may be added at any appropriate stage during formulation formation.

[0131] In either embodiment, the mixture containing the rheology modifier can be subjected to high shear to actively activate the rheology modifier. The mixture can be exposed to high shear at any suitable stage during the formation of the formulation, as will be understood by one of skill in the art.

[0132] VI. Specific Embodiments The present disclosure contemplates, among other things, the following numbered embodiments:

[0133] 1. Structure [ka] and a compound having the formula: a lipophilic solvent; a first dispersant; a rheology modifier; and A composition comprising:

[0134] 2. The composition of embodiment 1, wherein the compound is substantially insoluble in the lipophilic solvent.

[0135] 3. The composition of embodiment 1 or embodiment 2, wherein the compound is present in the form of particles having a volume-weighted median particle size in the range of from greater than 0.01 microns to 20 microns.

[0136] 4. The composition of embodiment 3, wherein the volume weighted median particle diameter is from 0.1 microns to 5 microns.

[0137] 5. The composition of embodiment 1, wherein the volume weighted median particle size of the compound is less than about 15 microns as measured by light scattering.

[0138] 6. The formulation of embodiment 1, wherein the volume weighted median particle size of the compound is less than about 7 microns as measured by light scattering.

[0139] 7. The composition of embodiment 3, wherein the volume weighted median particle diameter is from 0.5 microns to 2 microns.

[0140] 8. The formulation of embodiment 1, wherein the volume weighted median particle size of the compound is about 1 micron or less, as measured by light scattering.

[0141] 9. The composition of any one of embodiments 1-8, wherein the lipophilic solvent comprises a mineral oil, a fatty acid, a vegetable or seed oil, a terpene, an aliphatic solvent, a cyclic hydrocarbon solvent, an aromatic solvent, or derivatives and / or combinations thereof.

[0142] 10. The composition of embodiment 9, wherein the lipophilic solvent comprises a fatty acid derivative.

[0143] 11. The composition of embodiment 10, wherein the fatty acid derivative is selected from fatty acid esters, fatty acid dialkylamides, and combinations thereof.

[0144] 12. The composition of embodiment 10, wherein the fatty acid derivative comprises methyl oleate.

[0145] 13. The composition of embodiment 9, wherein the lipophilic solvent comprises a paraffinic solvent.

[0146] 14. The composition of embodiment 9, wherein the lipophilic solvent comprises an aromatic solvent.

[0147] 15. The composition of embodiment 9, wherein the lipophilic solvent comprises tetrahydronaphthalene, alkylated naphthalene, derivatives thereof, or combinations thereof.

[0148] 16. The composition of any one of embodiments 3 to 8, wherein the particles are present in an amount of 5% to 90% by weight.

[0149] 17. The composition of any one of embodiments 3 to 8, wherein the particles are present in an amount of 30% to 85% by weight.

[0150] 18. The composition of any one of embodiments 3 to 8, wherein the particles are present in an amount of 30% to 50% by weight.

[0151] 19. The composition of any one of the preceding embodiments, wherein the rheology modifier comprises an organically modified clay, silica or hydrophobically modified silica, alumina, a polyurethane-based polymer, or a combination thereof.

[0152] 20. The composition of any one of embodiments 1-19, wherein the rheology modifier is present in an amount of 0.1% to 15% by weight.

[0153] 21. The composition of embodiment 20, wherein the rheology modifier is present in an amount of 1% to 10% by weight.

[0154] 22. The composition of any one of embodiments 1-21, wherein the first dispersant has a molecular weight of 1,000 Daltons to 100,000 Daltons and is completely soluble in the lipophilic solvent.

[0155] 23. The composition of any one of embodiments 1-22, wherein the first dispersant is an anionic dispersant, a cationic dispersant, a nonionic dispersant, or a combination thereof.

[0156] 24. The composition of any one of embodiments 1-23, wherein the first dispersant is an anionic dispersant.

[0157] 25. The composition of any one of embodiments 1-23, wherein the first dispersant is a non-ionic dispersant.

[0158] 26. The composition of any one of the preceding embodiments, wherein the first dispersant is selected from a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof.

[0159] 27. The composition of any one of embodiments 1-25, wherein the first dispersant is a copolymer.

[0160] 28. The composition of embodiment 27, wherein the copolymer is a random or statistical copolymer, a block copolymer, a comb block copolymer, or a combination thereof.

[0161] 29. The composition of any one of embodiments 1-26, wherein the first dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyvinyl sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinate, vinylpyrrolidone / vinyl caprolactam, polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohol, polyethoxylated diamine, naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, ethoxylated lignosulfonate, or a combination thereof.

[0162] 30. The composition of any one of embodiments 1-29, wherein the first dispersant is present in an amount of 0.1% to 20% by weight.

[0163] 31. The composition of embodiment 30, wherein the first dispersant is present in an amount of 1% to 10% by weight.

[0164] 32. The composition of any one of embodiments 1-31, further comprising an emulsifier and a second dispersing agent.

[0165] 33. The composition of embodiment 32, wherein the emulsifier has a molecular weight of 150 Daltons to 1,200 Daltons.

[0166] 34. The composition of embodiment 32 or embodiment 33, wherein the emulsifier is an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, a zwitterionic surfactant, or a combination thereof.

[0167] 35. The composition of embodiment 34, wherein the emulsifier is selected from an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof.

[0168] 36. The anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate ester of an alcohol, an alcohol ethoxylate, a tristyrylphenol ethoxylate, a fatty acid, or a natural oil, or any combination thereof; the cationic surfactant is an ethoxylated amine of a natural oil, an alcohol, a fatty acid, or a combination thereof; or Embodiment 36. The composition of embodiment 34 or embodiment 35, wherein the nonionic surfactant is a polyethoxylate and / or polypropoxylate of an alcohol, a natural oil, or a combination thereof.

[0169] 37. The composition of any one of embodiments 1-36, wherein the composition does not contain more than 0.1% by weight of compounds containing primary amines, secondary amines, and / or tertiary amines.

[0170] 38. The composition of any one of embodiments 1-37, wherein the composition does not contain more than 0.1% by weight of a quaternary ammonium compound.

[0171] 39. The composition of any one of embodiments 32-38, wherein the second dispersant has a molecular weight of 1,000 Daltons to 100,000 Daltons and is water soluble.

[0172] 40. The composition of any one of embodiments 1-39, further comprising an agriculturally active compound A.

[0173] 41. An agricultural composition comprising water and / or a lipophilic solvent and the composition of any one of embodiments 1 to 40.

[0174] 42. The agricultural composition of embodiment 41, wherein the agricultural composition comprises 0.01% to 10% by weight of the formulation of any one of embodiments 1 to 40.

[0175] 43. The agricultural composition of embodiment 41 or embodiment 42, wherein the agricultural composition further comprises an agriculturally active compound B.

[0176] 44. The composition of embodiment 40 or the agricultural composition of any one of embodiments 38-39, wherein the composition or agricultural composition comprises at least one of the agriculturally active compound A or the agriculturally active compound B, and each of the agriculturally active compound A and the agriculturally active compound B is independently an acaricide, antimicrobial, fungicide, herbicide, insecticide, molluscicide, or nematicide, or a combination thereof.

[0177] 45. The composition or agricultural composition of embodiment 44, wherein each of the agriculturally active compound A and the agriculturally active compound B is independently a fungicide.

[0178] 46. ​​Each of the agriculturally active compound A and the agriculturally active compound B is independently a benzimidazole fungicide, a dicarboximide fungicide, a phenylpyrrole fungicide, an anilinopyrimidine fungicide, a hydroxyanilide fungicide, a carboxamide fungicide, a phenylamide fungicide, a phosphonate fungicide, a cinnamate fungicide, an OSBPI fungicide, a triazolecarboxamide fungicide, a Group 27 fungicide, a carbamate fungicide, a benzamide fungicide, a demethylation inhibitor fungicide, a piperazine fungicide, a pyrimidine fungicide, or an imidazole. 45. The agricultural composition of embodiment 44, wherein the fungicide is selected from a fungicide, a triazole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a QoI strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper fungicide, a sulfur fungicide, a lime sulfur fungicide, an ethylene bisdithiocarbamate (EBDC) fungicide, an EBDC fungicide, an aromatic hydrocarbon fungicide, a chloronitrile fungicide, a phthalimide fungicide, a guanidine fungicide, a QiI fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0179] 47. Each of the agriculturally active compounds A and B is independently selected from the group consisting of benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen benzovindiflupyr, solatenol (benzovindiflupyr), mefenoxam, metalaxyl, oxadixyl, aluminum tris, phosphorous acid, dimethomorph, mandipropamide, oxathiapiproline, ethaboxam, cymoxanil, propamocarb, fluopicolide, triforine, fenarimol, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole, metconazole, ibuprofen Puconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoline 45. The agricultural composition of embodiment 44, wherein the fungicide is selected from xifene, Bordeaux, cupric ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dicloran (DCNA), etridizole, pentachloronitrobenzene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluthianil, or combinations thereof.

[0180] 48. A method of using the agricultural composition of any one of embodiments 41 to 47, comprising applying the agricultural composition to a plant, a plant part, a seed, the soil in which a plant is growing or to be grown, or the soil in which a seed has been sown or to be sown.

[0181] 49. A method for controlling or preventing fungal growth, comprising applying an agricultural composition according to any one of embodiments 41 to 47 to a site experiencing fungal growth or at risk of developing fungal growth.

[0182] 50. A method for controlling or preventing fungal growth, comprising: diluting the composition of any one of embodiments 1 to 40 or embodiments 44 to 47 with water and / or a lipophilic solvent to form a diluted mixture; applying the diluted mixture to an area experiencing fungal growth or an area at risk of developing fungal growth; The method comprising:

[0183] 51. The method of embodiment 50, wherein the composition is a composition described in any one of embodiments 1 to 39, and diluting the composition further comprises adding an agriculturally active compound.

[0184] 52. The method of embodiment 50, wherein adding the agriculturally active compound comprises adding an amount of the agriculturally active compound that is less than the amount of the agriculturally active compound recommended for use in the absence of the composition of any one of embodiments 1-39.

[0185] 53. The agriculturally active compound is a benzimidazole fungicide, a dicarboximide fungicide, a phenylpyrrole fungicide, an anilinopyrimidine fungicide, a hydroxyanilide fungicide, a carboxamide fungicide, a phenylamide fungicide, a phosphonate fungicide, a cinnamate fungicide, an OSBPI fungicide, a triazolecarboxamide fungicide, a Group 27 fungicide, a carbamate fungicide, a benzamide fungicide, a demethylation inhibitor fungicide, a piperazine fungicide, a pyrimidine fungicide, an imidazole fungicide, a triazole fungicide, a mol 53. The method of any one of embodiments 51-52, wherein the fungicide is selected from a folin fungicide, a Group U6 fungicide, a Group 50 fungicide, a QoI strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper fungicide, a sulfur fungicide, a lime sulfur fungicide, an ethylene bisdithiocarbamate (EBDC) fungicide, an EBDC fungicide, an aromatic hydrocarbon fungicide, a chloronitrile fungicide, a phthalimide fungicide, a guanidine fungicide, a QiI fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0186] 54. The agriculturally active compound is benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen, solatenol (benzovindiflupyr), Mefenoxam, metalaxyl, oxadixyl, aluminum tris, phosphorous acid, dimethomorph, mandipropamide, oxathiapiproline, ethaboxam, cymoxanil, propamocarb, fluopicolide, triforine, fenarimol, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole, metconazole, ipconazole, myclobutanil, promethazine The method of any one of embodiments 51-42, wherein the fungicide is selected from lopiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperaline, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dicloran (DCNA), etridizole, pentachloronitrobenzene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluthianil, or combinations thereof.

[0187] 55. Use of the agricultural composition according to any one of embodiments 41 to 47 for application to a plant, a plant part, a seed, the soil in which a plant is growing or will grow, or the soil in which a seed has been sown or will be sown.

[0188] 56. Use of the agricultural composition according to any one of embodiments 41 to 47 for controlling or preventing fungal growth at sites where fungal growth occurs or at risk of developing fungal growth. [Example]

[0189] VII. Working Examples Example 1 An oil-flowable formulation is prepared as follows: 2 g of Luvitec® K30 (polyvinylpyrrolidinone) is dissolved in 53 g of Exxsol® D80 paraffinic solvent, 5 g of Attagel® 50 rheology modifier is added, and the mixture is subjected to high shear to activate the rheology modifier.

[0190] Disperse 40 g of (£)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, previously air-milled to a median particle size of less than 2 microns, in this mixture. This oil-flowable formulation is expected to have excellent chemical and physical stability.

[0191] Example 2 An oil dispersible formulation is prepared as follows: 2g of Luvitec K30 is dissolved in 46g of Steposol™ ME (methyl oleate / methyl linoleate). 5g of Borchi® Gel 0434 rheology modifier is added along with 3g of Plurafac® LF 700, 4g of Agnique® ABS 60 C-EH emulsifiers.

[0192] Into this mixture is dispersed 40 g of (£)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, previously air-milled to a median particle size of less than 2 microns. This oil-dispersible formulation is expected to have excellent chemical and physical stability.

[0193] Example 3 chemical stability Samples are prepared according to the methods described herein, such as in Example 1 above, except that certain subsamples are spiked with low concentrations of specific components, including primary, secondary, tertiary, or quaternary amines. The chemical stability of the samples is assessed by storing them at elevated temperatures and periodically measuring the remaining concentration of the active ingredient by HPLC. Reference samples are stored at lower temperatures and are also tested at the same time points. It is anticipated that certain components may promote chemical degradation and may need to be excluded from the formulations of the present invention.

[0194] In view of the many possible embodiments to which the principles of the disclosed invention may be applied, it should be recognized that the illustrated embodiments are only preferred examples of the invention and should not be construed as limiting the scope of the invention. Rather, the scope of the invention is defined by the following claims. The inventors therefore claim as their invention all that comes within the spirit and scope of these claims. [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6] [Table 2-7] [Table 2-8] [Table 2-9] Table 2-10 Table 2-11 Table 2-12 Table 2-13 Table 2-14 Table 3-1 Table 3-2 Table 3-3 Table 3-4 Table 3-5 Table 3-6 Table 3-7 Table 3-8 Table 3-9 Table 3-10 Table 3-11 Table 3-12 Table 3-13 Table 3-14 Table 3-15 Table 3-16 Table 3-17 Table 3-18 Table 3-19 Table 3-20 Table 3-21 Table 3-22 Table 3-23 Table 3-24 Table 4-1 Table 4-2 Table 4-3 Table 4-4 Table 4-5 Table 4-6 Table 4-7 Table 4-8 Table 4-9 Table 4-10

Claims

1. structure 【Chemistry 4】 and a compound having the formula: a lipophilic solvent; a first dispersant; and a rheology modifier; and A composition comprising:

2. The composition of claim 1 , wherein the compound is substantially insoluble in the lipophilic solvent.

3. 3. The composition of claim 1 or claim 2, wherein the compound is present in the form of particles having a volume weighted median particle size in the range of from greater than 0.01 microns to 20 microns.

4. 4. The composition of claim 3, wherein the volume weighted median particle size is from 0.1 microns to 5 microns.

5. 10. The formulation of claim 1, wherein the volume weighted median particle size of the compound is less than about 15 microns as measured by light scattering.

6. 10. The formulation of claim 1, wherein the volume weighted median particle size of the compound is less than about 7 microns as measured by light scattering.

7. 4. The composition of claim 3, wherein the volume weighted median particle size is from 0.5 microns to 2 microns.

8. 10. The formulation of claim 1, wherein the volume weighted median particle size of the compound is about 1 micron or less as measured by light scattering.

9. 9. The composition of any one of claims 1 to 8, wherein the lipophilic solvent comprises a mineral oil, a fatty acid, a vegetable or seed oil, a terpene, an aliphatic solvent, a cyclic hydrocarbon solvent, an aromatic solvent, or derivatives and / or combinations thereof.

10. The composition of claim 9 , wherein the lipophilic solvent comprises a fatty acid derivative.

11. 11. The composition of claim 10, wherein the fatty acid derivative is selected from fatty acid esters, fatty acid dialkylamides, and combinations thereof.

12. The composition of claim 10 , wherein the fatty acid derivative comprises methyl oleate.

13. The composition of claim 9 , wherein the lipophilic solvent comprises a paraffinic solvent.

14. The composition of claim 9 , wherein the lipophilic solvent comprises an aromatic solvent.

15. 10. The composition of claim 9, wherein the lipophilic solvent comprises tetrahydronaphthalene, alkylated naphthalene, derivatives thereof, or combinations thereof.

16. A composition according to any one of claims 3 to 8, wherein the particles are present in an amount of from 5% to 90% by weight.

17. A composition according to any one of claims 3 to 8, wherein the particles are present in an amount of from 30% to 85% by weight.

18. A composition according to any one of claims 3 to 8, wherein the particles are present in an amount of from 30% to 50% by weight.

19. The composition of any one of claims 1 to 18, wherein the rheology modifier comprises an organically modified clay, silica or hydrophobically modified silica, alumina, a polyurethane-based polymer, or a combination thereof.

20. The composition of any one of claims 1 to 19, wherein the rheology modifier is present in an amount of 0.1% to 15% by weight.

21. 21. The composition of claim 20, wherein the rheology modifier is present in an amount of from 1% to 10% by weight.

22. 22. The composition of any one of claims 1 to 21, wherein the first dispersant has a molecular weight of from 1,000 Daltons to 100,000 Daltons and is completely soluble in the lipophilic solvent.

23. The composition of any one of claims 1 to 22, wherein the first dispersant is an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof.

24. The composition of any one of claims 1 to 23, wherein the first dispersant is an anionic dispersant.

25. The composition of any one of claims 1 to 23, wherein the first dispersant is a non-ionic dispersant.

26. The composition of any one of claims 1 to 25, wherein the first dispersant is selected from a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof.

27. The composition of any one of claims 1 to 25, wherein the first dispersant is a copolymer.

28. 28. The composition of claim 27, wherein the copolymer is a random or statistical copolymer, a block copolymer, a comb block copolymer, or a combination thereof.

29. 27. The composition of any one of claims 1 to 26, wherein the first dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyvinyl sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinate, vinylpyrrolidone / vinyl caprolactam, polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohols, polyethoxylated diamines, naphthalene sulfonic acid formaldehyde condensates, lignosulfonates, ethoxylated lignosulfonates, or combinations thereof.

30. 30. The composition of any one of claims 1 to 29, wherein the first dispersant is present in an amount of 0.1% to 20% by weight.

31. 31. The composition of claim 30, wherein the first dispersant is present in an amount of from 1% to 10% by weight.

32. The composition of any one of claims 1 to 31, further comprising an emulsifier and a second dispersing agent.

33. 33. The composition of claim 32, wherein the emulsifier has a molecular weight of from 150 Daltons to 1,200 Daltons.

34. 34. The composition of claim 32 or claim 33, wherein the emulsifier is an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, a zwitterionic surfactant, or a combination thereof.

35. 35. The composition of claim 34, wherein the emulsifier is selected from an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof.

36. the anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate ester of an alcohol, an alcohol ethoxylate, a tristyrylphenol ethoxylate, a fatty acid, or a natural oil, or any combination thereof; the cationic surfactant is an ethoxylated amine of a natural oil, an alcohol, a fatty acid, or a combination thereof; or 36. The composition of claim 34 or claim 35, wherein the nonionic surfactant is a polyethoxylate and / or polypropoxylate of an alcohol, a natural oil, or a combination thereof.

37. 37. The composition of any one of claims 1 to 36, wherein the composition does not contain more than 0.1% by weight of compounds containing primary amines, secondary amines, and / or tertiary amines.

38. The composition of any one of claims 1 to 37, wherein the composition does not contain more than 0.1% by weight of quaternary ammonium compounds.

39. 39. The composition of any one of claims 32 to 38, wherein the second dispersant has a molecular weight of from 1,000 Daltons to 100,000 Daltons and is water soluble.

40. 40. The composition according to any one of claims 1 to 39, further comprising an agriculturally active compound A.

41. An agricultural composition comprising water and / or a lipophilic solvent and a composition according to any one of claims 1 to 40.

42. 42. The agricultural composition of claim 41, wherein the agricultural composition comprises from 0.01% to 10% by weight of the formulation of any one of claims 1 to 40.

43. 43. The agricultural composition of claim 41 or claim 42, wherein the agricultural composition further comprises an agriculturally active compound B.

44. 41. The composition of claim 40 or the agricultural composition of any one of claims 38 to 39, wherein the composition or agricultural composition comprises at least one of the agriculturally active compound A or the agriculturally active compound B, and each of the agriculturally active compound A and the agriculturally active compound B is independently an acaricide, antibacterial agent, fungicide, herbicide, insecticide, molluscicide, or nematicide, or a combination thereof.

45. 45. The composition or agricultural composition of claim 44, wherein each of the agriculturally active compound A and the agriculturally active compound B is independently a fungicide.

46. Each of the agriculturally active compounds A and B may independently be a benzimidazole fungicide, a dicarboximide fungicide, a phenylpyrrole fungicide, an anilinopyrimidine fungicide, a hydroxyanilide fungicide, a carboxamide fungicide, a phenylamide fungicide, a phosphonate fungicide, a cinnamate fungicide, an OSBPI fungicide, a triazolecarboxamide fungicide, a Group 27 fungicide, a carbamate fungicide, a benzamide fungicide, a demethylation inhibitor fungicide, a piperazine fungicide, a pyrimidine fungicide, an imidazole fungicide, a 45. The agricultural composition of claim 44, wherein the fungicide is selected from a fungicide, a triazole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a Qol strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper fungicide, a sulfur fungicide, a lime sulfur fungicide, an ethylene bisdithiocarbamate (EBDC) fungicide, an EBDC fungicide, an aromatic hydrocarbon fungicide, a chloronitrile fungicide, a phthalimide fungicide, a guanidine fungicide, a Qil fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

47. Each of the agriculturally active compound A and the agriculturally active compound B may independently be selected from the group consisting of benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen, Solatenol (benzovindiflupyr), mefenoxam, metalaxyl, oxadixyl, aluminum tris, phosphorous acid, dimethomorph, mandipropamide, oxathiapiproline, ethaboxam, cymoxanil, propamocarb, fluopicolide, triforine, fenarimol, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole, metconazole, ip Conazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoline 45. The agricultural composition of claim 44, wherein the fungicide is selected from xifene, Bordeaux, cupric ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dicloran (DCNA), etridizole, pentachloronitrobenzene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluthianil, or combinations thereof.

48. 48. A method of using the agricultural composition of any one of claims 41 to 47, comprising applying the agricultural composition to a plant, a plant part, a seed, the soil in which a plant is growing or will grow, or the soil in which a seed has been sown or will be sown.

49. 50. A method of controlling or preventing fungal growth, which method comprises applying an agricultural composition according to any one of claims 41 to 47 to a site where fungal growth is occurring or at risk of occurring.

50. 1. A method for controlling or preventing fungal growth, comprising: diluting the composition of any one of claims 1 to 40 or claims 44 to 47 with water and / or a lipophilic solvent to form a diluted mixture; applying the diluted mixture to an area experiencing fungal growth or an area at risk of developing fungal growth; The method comprising:

51. 51. The method of claim 50, wherein the composition is a composition of any one of claims 1 to 39, and diluting the composition further comprises adding an agriculturally active compound.

52. 51. The method of claim 50, wherein adding the agriculturally active compound comprises adding an amount of the agriculturally active compound that is less than the amount of the agriculturally active compound recommended for use in the absence of the composition of any one of claims 1 to 39.

53. The agriculturally active compound may be a benzimidazole fungicide, a dicarboximide fungicide, a phenylpyrrole fungicide, an anilinopyrimidine fungicide, a hydroxyanilide fungicide, a carboxamide fungicide, a phenylamide fungicide, a phosphonate fungicide, a cinnamate fungicide, an OSBPI fungicide, a triazolecarboxamide fungicide, a Group 27 fungicide, a carbamate fungicide, a benzamide fungicide, a demethylation inhibitor fungicide, a piperazine fungicide, a pyrimidine fungicide, an imidazole fungicide, a triazole fungicide, a morpholine fungicide, a methylaminopyrimidine ...

53. The method of any one of claims 51-52, wherein the fungicide is selected from a phosphorus fungicide, a Group U6 fungicide, a Group 50 fungicide, a Qol strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper fungicide, a sulfur fungicide, a lime sulfur fungicide, an ethylene bisdithiocarbamate (EBDC) fungicide, an EBDC fungicide, an aromatic hydrocarbon fungicide, a chloronitrile fungicide, a phthalimide fungicide, a guanidine fungicide, a Qil fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

54. The agriculturally active compounds include benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen, solatenol (benzovindiflupyr), mef Enoxam, metalaxyl, oxadixyl, aluminum tris, phosphorous acid, dimethomorph, mandipropamid, oxathiapiproline, ethaboxam, cymoxanil, propamocarb, fluopicolide, triforine, fenarimol, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole, metconazole, ipconazole, myclobutanil, pro 53. The method of any one of claims 51 to 42, wherein the fungicide is selected from piconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperaline, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoxyfen, Bordeaux, cupric ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dicloran (DCNA), etridizole, pentachloronitrobenzene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, flutianil, or a combination thereof.

55. 48. Use of the agricultural composition according to any one of claims 41 to 47 for application to a plant, a plant part, a seed, the soil in which a plant is growing or will grow, or the soil in which a seed has been or will be sown.

56. 48. Use of an agricultural composition according to any one of claims 41 to 47 to control or prevent fungal growth at a site where fungal growth is occurring or at risk of developing fungal growth.

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