Water-dispersible granular acylhydrazone apyrase inhibitor formulation

Abstract

Disclosed herein are embodiments of water-dispersible granules (and compositions / formulations thereof) comprising a first active compound having structure (I), a dispersant, and, optionally, a dust control agent. In one embodiment, the water-dispersible granule comprises particles of the first agriculturally active compound present in an amount ranging from 5% to 90%, 0.5% to 15%, 30% to 85%, 30% to 40%, or 70% to 85% by weight. In one embodiment of the disclosed water-dispersible granules, the dispersant is present in an amount ranging from 1% to 30% by weight, e.g., from about 2% to about 15%, or from about 3% to about 20% by weight, particularly about 1%, about 3%, about 5%, about 10%, or about 20% by weight. TIFF2026502772000065.tif23165

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 / 419,635, filed October 26, 2022, which is incorporated herein by reference in its entirety.

[0002] The present disclosure relates to water-dispersible granules containing apyrase inhibitors 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 a range of mechanisms to survive pesticides, for example, by sequestering, exporting, or detoxifying them. 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] Provided herein is a water-dispersible granule comprising particles of a first agriculturally active compound having the structure: [ka] a dispersant; and and optionally a dust suppressant, wherein the particles of the first active compound have a volume weighted median particle size in the range of greater than 0.01 microns to 20 microns.

[0005] In one embodiment, the water-dispersible granules comprise particles of a first agriculturally active compound present in an amount ranging from 5% to 90% by weight, 0.5% to 15% by weight, 30% to 85% by weight, 30% to 40% by weight, or 70% to 85% by weight.

[0006] In one embodiment of the disclosed water-dispersible granules, the dispersant is present in an amount ranging from 1% to 30% by weight, for example, from about 2% to about 15% by weight, or from about 3% to about 20% by weight, particularly about 1%, about 3%, about 5%, about 10%, or about 20% by weight.

[0007] In certain embodiments, the dispersant is a high molecular weight dispersant.

[0008] In one embodiment of the disclosed water-dispersible granules, the dispersant has a molecular weight in the range of 400 Daltons to 2,000,000 Daltons, for example, in the range of 1,000 Daltons to 100,000 Daltons. Dispersants suitable for use in the water-dispersible granules include anionic dispersants, cationic dispersants, nonionic dispersants, and combinations thereof. In certain embodiments, the dispersant is selected from homopolymer dispersants, random or statistical copolymers, block copolymers, or combinations thereof. In particular examples, the 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 combinations thereof.

[0009] In one embodiment of the disclosed water-dispersible granules, a dust suppressant is included. In such an embodiment, the dust suppressant is a liquid or a low-melting-point solid. In certain embodiments, the dust suppressant is selected from surfactants, waxes, natural oils, chemically modified natural oils, low-volatility organic solvents, or combinations thereof.

[0010] In further embodiments, the water-dispersible granules disclosed herein may additionally comprise a binder. For example, in some embodiments, the binder is present in an amount ranging from 5% to 30% by weight, for example, from 10% to 25% by weight. In one embodiment, the water-dispersible granules comprise a binder selected from compounds having a melting point above 100°C and that completely dissolve in water during the granulation process.

[0011] Exemplary embodiments of the water-dispersible granules also optionally include one or more inert carriers, diluents, or combinations thereof. In certain such embodiments, the inert carriers or diluents are included in an amount sufficient to make up the total weight balance of the water-dispersible granules to 100% by weight. In certain embodiments, the inert carriers or diluents are selected from starch, wood flour, cellulose, chemically modified cellulose, or inorganic materials. Suitable inorganic materials include clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, alone or in combination with other inorganic materials, other carriers, or diluents, or both.

[0012] In certain embodiments, the water-dispersible granules contain an antifoaming agent. In certain such embodiments, the antifoaming agent is an emulsion of silicone oil. In one embodiment of the water-dispersible granules disclosed herein, the antifoaming agent is present in an amount ranging from 0.01% to 1% by weight.

[0013] In one embodiment of the water-dispersible granules, particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume-weighted median particle size in the range of from greater than 0.01 microns to 10 microns. In one embodiment, the particle size, measured by light scattering after dilution and dispersion of the particles in water, is in the range of from greater than 0.01 microns to 10 microns, e.g., greater than 0.01 microns to 5 microns, or greater than 0.01 microns to 2 microns. In one embodiment, the particle size is about 1 micron or less, e.g., less than about 1 micron, 0.01 micron to about 15 microns, e.g., about 1 micron to about 15 microns, or about 1 micron to about 7 microns.

[0014] In one embodiment of the water-dispersible granules disclosed herein, the granules comprise: (a) particles of a first agriculturally active compound having the following structure: [ka] particles present in an amount ranging from 5% to 85% by weight; and (b) 0.5% to 15% by weight of a dust suppressant selected from a surfactant, a wax, a natural oil, a chemically modified natural oil, a low-volatility organic solvent, or a combination thereof. In further embodiments of such water-dispersible granules, the granules comprise 3% to 20% by weight of a high molecular weight dispersant. In embodiments of such water-dispersible granules, the particles of the first agriculturally active compound have a volume weighted median particle size of less than 20 microns, e.g., about 15 microns or less, about 10 microns or less, about 7 microns or less, e.g., less than about 2 microns, e.g., the particles have a volume weighted median particle size of about 1 micron.

[0015] In some embodiments, the water-dispersible granules disclosed herein further comprise an additional agriculturally active compound. Examples of the additional agriculturally active compound may be selected from fungicides, repellents, herbicides, insecticides, molluscicides, and nematicides. In certain embodiments, two or more additional agriculturally active compounds are included in the disclosed water-dispersible granules, so that a combination of additional agriculturally active compounds is included.

[0016] By way of example, in certain embodiments, the additional agriculturally active compound included in the water-dispersible granules disclosed herein is a fungicide, such as 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 cinnamic acid fungicide, an oxysterol-binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a hydroxyanilide ... The fungicide is selected from fungicides, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, strobilin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0017] More specifically, when the additional agriculturally active compound included in the water-dispersible granules of the present invention is a fungicide, particularly useful fungicides for use include benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxyl 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, mefentri Fluconazole, metconazole, ipconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin The antibacterial agents include those selected from the group consisting of benzophenone, 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.

[0018] In certain embodiments, water is added to the water-dispersible granules disclosed herein. In one embodiment, the water-dispersible granules are present in the composition in an amount sufficient to enhance the biological effect of the additional agriculturally active compound, such that the total amount of the additional agriculturally active compound in the composition applied to the crop or produce is lower than would typically be required and / or recommended to achieve the same biological effect in a composition that does not include the water-dispersible granules.

[0019] Particularly useful in the compositions and methods disclosed herein are fungicides, such as benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyanilide fungicides, carboxamide fungicides, phenylamide fungicides, phosphonate fungicides, cinnamic acid fungicides, oxysterol binding protein inhibitor (OSBPI) fungicides, triazole carboxamide fungicides, carbamate fungicides, Group 27 fungicides, benzamide fungicides, demethylation-inhibiting piperazine fungicides, and demethylation-inhibiting pyrimidine fungicides. and the additional agriculturally active compound is selected from a group consisting of a benzophenone-3, benzophenone-4, benzotriazole, benzotriazole, benzotriazole-4 ...

[0020] The disclosed compositions are typically applied to plants, plant parts, seeds, the soil in which the plants are growing or will be growing, or the soil in which the seeds have been or will be sown. In one embodiment, the application site is selected as being at risk of or already containing fungal growth.

[0021] In one embodiment, the water-dispersible granules disclosed herein comprise particles of a first active compound having a volume-weighted median particle size in the range of greater than 0.01 to 20 microns, as measured by light scattering after dilution and dispersion of the WDG in water. The water-dispersible granules may also comprise an inert carrier and / or diluent. Agricultural compositions comprising the water-dispersible granules and methods of using the same are also disclosed. The compositions may also comprise an agriculturally active compound, such as an acaricide, antimicrobial, fungicide, herbicide, insecticide, molluscicide, or nematicide, or a combination thereof, and an antifoaming agent.

[0022] The foregoing and other objects, features, and advantages of the present disclosure will become apparent from the following detailed description which proceeds with reference to the accompanying drawings. DETAILED DESCRIPTION OF THE INVENTION

[0023] I. Terminology Overview 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.

[0024] 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.

[0025] 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.

[0026] "Administering" refers to any suitable mode of administration for controlling pathogens, such as fungal pathogens, including treatment of existing crops, seeds, soil, or combinations thereof.

[0027] "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.

[0028] "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.

[0029] As used herein, the term "potentiator" refers to a compound or compounds disclosed herein that enhance the effectiveness of a pesticide. Without being limited by theory, the potentiator compounds disclosed herein may function by blocking one or more pathways by which pathogens, such as fungal pathogens, avoid toxicity, such as by detoxifying, sequestering, or excreting the pesticide. In certain embodiments, the potentiator compounds disclosed herein inhibit the enzyme apyrase activity, which leads to the enhancement, emphasis, or potentiation of pesticides, such as acaricides, antimicrobials, fungicides, herbicides, insecticides, molluscicides, and / or nematicides. For example, when a potentiator compound is used in conjunction with a fungicide, the combination of the potentiator and the fungicide enhances the fungicidal effect of the fungicide, and / or as a result of the potentiator's activity, fungi that have previously been resistant to the fungicide become susceptible to the fungicide. In most cases, these potentiators themselves do not 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.

[0030] 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 field and / or target area of ​​a plant. Treatment methods can be, but are not limited to, aerosol spray, pressurized spray, atomization, chemigation, direct watering, 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, tuberous roots, 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., the foliage is treated when the disclosed compounds are applied to the shoots when applied to the root zone or foliage).

[0031] As used herein, the term "water-dispersible granules" or "WDG" refers to a dry solid formulation in granular form containing the enhancer compound disclosed herein. WDGs typically have a larger average particle size than wettable powder particles, thus producing less dust and being more flowable. When added to water, WDGs disperse and / or dissolve to produce a fine particle suspension of the enhancer compound. WDGs can be stored as a formulation and provided to markets and / or end users without further processing. In actual use, WDGs are prepared for application by end users. Typically, WDGs are mixed with water in an end user's spray tank to produce a fine particle suspension of a concentration suitable for the particular application. The concentration may vary depending on the crop, pathogen, time of year, geography, local regulations, and degree of infestation, among other factors. Once mixed with water at the desired concentration, the resulting fine particle suspension can be applied, such as by spraying.

[0032] II. Formulation A common goal for agricultural product formulators is to maximize the biological activity of their active ingredients. This is particularly challenging for wettable powders and dry powders (WDGs), which are typical types of solid formulations, because the solid state of the active ingredient tends to limit its bioavailability and / or such powders pose an inhalation hazard and / or are not easily applied. While not limited by theoretical understanding, factors that may determine biological activity currently include solubility in water (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 are potentially discoverable by formulators, 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.

[0033] Among the formulations tested during the work described in this disclosure, the inventors discovered that aqueous suspensions of (£)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally exhibited low biological activity. Furthermore, it was discovered that controlling the particle size of (£)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide in water-dispersible granules (or "WDG") containing the ingredients described herein significantly improved biological activity by controlling the particle size of the (£)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide within a specific size range.

[0034] 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 phases present (including the hydrophobic phase of any surfactant micellar structure), the presence in those liquid phases of chemical species that can catalyze degradation, any tendency of the active ingredient to undergo autocatalysis, whereby degradation products accelerate further reactions, 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.

[0035] 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. It was further discovered that acceptable chemical stability could be obtained in WDGs containing the required ingredients described below by controlling the pH within specific ranges and by controlling the concentrations of certain ingredients that appear to catalyze decomposition. Furthermore, it was discovered that WDGs containing the ingredients described herein 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.

[0036] Disclosed herein is a WDG (and formulations thereof) that includes a first agriculturally active compound having the following structure: [ka] It is also known as (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0037] In some embodiments, the WDG comprises a first agriculturally active compound in addition to the dispersant and dust suppressant. In yet additional embodiments, the WDG may be formulated to include a binder, an inert carrier, an antifoaming agent, a diluent, or a combination thereof.

[0038] In some embodiments, the WDG is formulated to provide a particulate suspension when mixed with water, such as by an end user. In certain embodiments, the first agriculturally active compound and the dispersant are intimately mixed to provide a matrix that forms the WDG. The first agriculturally active compound can be fully or partially coated with the dispersant. The dust suppressant can also be present within the matrix or as a coating on the WDG.

[0039] A. First Agriculturally Active Compound The WDG comprises a first agriculturally active compound, (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, in an amount sufficient so that when prepared for use (e.g., combined with water), the first agriculturally active compound is present in an amount sufficient to enhance the effectiveness of one or more agriculturally active compounds that may be applied in combination with the first agriculturally active compound. In some embodiments, the WDG comprises 1% to 90% or more by weight of the first agriculturally active compound, for example, in an amount ranging from 5% to 90% by weight, or from 5% to 85% by weight, or from 10% to 85% by weight, or from 20% to 85% by weight, or from 30% to 85% by weight. In certain embodiments, the WDG comprises the first agriculturally active compound in an amount ranging from 5% to 90% by weight, e.g., from 30% to 85% by weight, or from 30% to 40% by weight, or from 70% to 85% by weight.

[0040] In some embodiments, at least a portion of the first agriculturally active compound is present in the WDG as particles. The particles of the first agriculturally active compound present in the WDG can have a volume-weighted median particle size ranging from greater than zero microns to 40 microns, e.g., from 0.01 microns to 40 microns, or from 0.01 microns to 30 microns, from 0.01 microns to 25 microns, from 0.01 microns to 20 microns, from 0.01 microns to 15 microns, from 0.01 microns to 10 microns, from 0.01 microns to 5 microns, or from 0.01 microns to 2 microns, as measured by light scattering after dilution and dispersion of the WDG in water. In certain embodiments, the particles of the first agriculturally active compound present in the WDG can have a volume-weighted median particle size ranging from 1 micron to 20 microns, e.g., from 1 micron to 15 microns, or from 2 microns to 10 microns, or from 4 microns to 8 microns, as measured by light scattering after dilution and dispersion of the WDG in water.

[0041] B. Dispersants The dispersant used to form the WDG of the present disclosure is typically a high molecular weight dispersant. In some embodiments, the dispersant may have a molecular weight of 400 daltons or greater, e.g., 400 daltons to 2,000,000 daltons, or 500 daltons to 1,000,000 daltons, or 750 daltons to 750,000 daltons, or 750 daltons to 500,000 daltons, or 1,000 daltons to 250,000 daltons, or 1,000 to 100,000 daltons. In certain embodiments, the dispersant has a molecular weight in the range of 1,000 to 100,000 daltons.

[0042] In some embodiments, the WDG comprises from greater than zero to 40 wt.% dispersant, for example, from 0.1 wt.% to 40 wt.% or more, or from 0.5 wt.% to 35 wt.%, or from 1 wt.% to 30 wt.%, or from 3 wt.% to 20 wt.% dispersant. In certain embodiments, the dispersant is present in an amount ranging from 1 wt.% to 30 wt.%, for example, from 3 wt.% to 20 wt.%.

[0043] In any embodiment, the dispersant can be selected from an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof. In some embodiments, the dispersant is or includes an anionic dispersant. In other embodiments, the dispersant is or includes a non-ionic dispersant. In any embodiment, the dispersant can be a low metal content dispersant, such as a low sodium dispersant, a low calcium dispersant, a low potassium dispersant, or a combination thereof. In yet additional embodiments, the dispersant can be a low metal content non-ionic dispersant, for example, a low sodium non-ionic dispersant, a low calcium non-ionic dispersant, a low potassium non-ionic dispersant, or a combination thereof.

[0044] In any embodiment, the dispersant may be selected from one or more of the following: homopolymer dispersants, such as, but not limited to, polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyvinyl sulfonate, polyethyleneimine, or combinations thereof; Random or statistical copolymers, such as, but not limited to, polyethylene glycol / polyisobutylene succinate, vinylpyrrolidone / vinylcaprolactam, or combinations thereof; Block copolymers, such as, but not limited to, polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohols, polyethoxylated diamines, or combinations thereof; Naphthalenesulfonic acid formaldehyde condensate, Lignosulfonates, Ethoxylated lignosulfonates, · or any combination of the above ingredients.

[0045] C. Dust suppressant One optional component of the WDG of the present disclosure is a dust suppressant. The dust suppressant used in the WDG is typically in the form of a liquid or a low-melting solid. In some embodiments, the low-melting solid is a compound that exists as a solid at ambient temperature but as a liquid at temperatures higher than ambient temperature, for example, above 30°C, above 35°C, or above 40°C. In certain embodiments, the dust suppressant can be selected from surfactants, waxes, natural oils, chemically modified natural oils, or low-volatility organic solvents.

[0046] Dust suppressant surfactants useful in the present WDG can be low molecular weight surfactants, for example, surfactants having a molecular weight ranging from 150 Daltons to less than 1,200 Daltons.

[0047] The dust suppressant surfactant 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.

[0048] In any embodiment, the anionic surfactant is a citrate, carbonate, phosphate, phosphonate, sulfate, or sulfonate. The anionic surfactant can 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 certain embodiments, the anionic surfactant is a citrate, carbonate, phosphate, phosphonate, sulfate, or sulfonate ester of an alcohol, an alcohol alkoxylate, a tristyrylphenol ethoxylate, a fatty acid, or a natural oil, or any combination thereof. In certain embodiments, the dust suppressant surfactant includes a lignosulfonate, for example, a dust suppressant surfactant comprising a mixture of lignosulfate and urea.

[0049] Cationic surfactants suitable for use as dust control agents include ethoxylated amines, for example, ethoxylated amines of natural oils, alcohols, fatty acids, or combinations thereof.

[0050] Suitable nonionic surfactants may include alkoxylates of alcohols, natural oils, synthetic oils, or combinations thereof, such as ethoxylates and / or propoxylates of alcohols, oils, or combinations thereof.

[0051] Suitable quaternary ammonium surfactants may include at least one chain having at least 6 carbon atoms attached to a quaternary ammonium head group, for example, 6 to 20 carbon atoms, or 6 to 12 carbon atoms.

[0052] Also, in some embodiments, the zwitterionic surfactants used herein as dust control agents contain a positively charged group, such as a quaternary ammonium group, and a negatively charged group, such as a carboxylic acid moiety, a sulfonic acid moiety, or a phosphate moiety. An example of a zwitterionic surfactant is cocamidopropyl betaine.

[0053] In certain embodiments, the surfactant is an anionic surfactant and may be selected from phosphate, phosphonate, sulfate, or sulfonate esters of alcohols, alcohol ethoxylates, tristyrylphenol ethoxylates, fatty acids, or natural oils, or any combination thereof.

[0054] In other embodiments, the surfactant is a non-ionic surfactant and may be selected from alkoxylates of alcohols, natural oils, or combinations thereof.

[0055] With particular reference to surfactants, one skilled in the art will understand that an 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.

[0056] Additional dust suppressants useful in the WDG of the present disclosure include waxes, such as but not limited to petroleum waxes or natural or plant-based waxes, and natural oils, such as but not limited to vegetable oils or animal oils.In certain embodiments, the natural oils used as dust suppressants are soybean oil, corn oil, olive oil, cottonseed oil, rapeseed oil, flax or any other seed or nut oil, castor oil, pine oil, tallow, or any combination thereof.Additional oils useful as dust suppressants in the WDG of the present disclosure include chemically modified oils, such as but not limited to methylated soybean oil, methyl oleate, or any combination thereof.

[0057] Low volatility organic solvents are also useful as dust suppressants herein. Examples of such low volatility organic solvents include, but are not limited to, paraffin or other mineral oil, tris-ethyl-hexyl phosphate, methyl benzoate, ethyl benzoate, propyl benzoate, or butyl benzoate, or other known plasticizers, or combinations thereof.

[0058] Without being limited by theory, it is understood that the mechanism of action of the dust suppressant is that while in a liquid state, the dust suppressant physically absorbs any fine particles and weakly binds them to larger granule particles. Thus, although the fine particles are not technically part of the granules and can be physically removed using special equipment such as an air jet sieve, the formation of airborne dust is substantially prevented. Airborne dust can be monitored by one of several methods known to those skilled in the art, such as an air jet sieve, or by observing or collecting the amount of material that remains suspended in the air when a sample of WDG is dropped into a container or air column.

[0059] The dust suppressant may be present in the WDG in an amount ranging from greater than zero to 25% by weight, such as from 0.1% to 20% by weight, or from 0.5% to 20% by weight, or from 0.5% to 15% by weight. In certain embodiments, the dust suppressant is present in an amount ranging from 0.5% to 15% by weight or from 0.1% to 2% by weight.

[0060] D. Optional Additives In some embodiments, the WDG itself, or a WDG formulation, may further comprise one or more additional ingredients, such as a binder, an antifoaming agent, an inert carrier, a diluent, or a combination thereof.

[0061] Suitable binders may include, but are not limited to, compounds that typically exist as solids at room temperature and have a melting point greater than 100°C. Binders are also typically completely dissolved in water during the granulation process. In some embodiments, the dispersants described herein may also function as binders. In some such embodiments, two (or more) dispersant compounds may be used, or a single dispersant may be used. In yet additional embodiments, a binder that is not a dispersant may be used. In such embodiments, sugars (e.g., ribose, xylose, glucose, fructose, mannose, sucrose, maltose, isomaltose, trehalose, xylitol, mannitol, sorbitol, dextrose, galactose, lactose, maltodextrin, saccharose, or combinations thereof), cellulose derivatives, synthetic and natural rubbers, synthetic polymers, and the like may be used as binders. In some embodiments, the binder may be selected from polyvinyl acetate, methylcellulose, hydroxymethylcellulose, or other modified cellulose, animal protein adhesive, guar gum, or modified guar gum, or combinations thereof, and in certain embodiments, the binder may be used in an amount ranging from 5% to 30% by weight, e.g., from 5% to 25% by weight, or from 10% to 25% by weight.

[0062] Suitable inert carriers and diluents may include, but are not limited to, compounds that typically exist as solid materials (e.g., fine powders) and have a melting point greater than 100°C. In some embodiments, the inert carriers and diluents are substantially insoluble in water and do not affect biological activity. Exemplary inert carriers and diluents may be selected from starch, wood flour, cellulose, chemically modified cellulose, minerals (e.g., clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, etc.), and combinations thereof. The inert carrier or diluent is included in an amount sufficient to make up the total weight balance of the water-dispersible granules to 100% by weight.

[0063] In some embodiments, the formulation includes one or more antifoaming agents. The antifoaming agent may be selected to reduce or prevent foaming during manufacture, handling, and / or use of the formulation. In some embodiments, the antifoaming agent is an emulsion of silicone oil. In some embodiments, the antifoaming agent is present in an amount ranging from 0.01% to 1.0% by weight.

[0064] E. Additional Agriculturally Active Compounds and Compositions WDG formulations may further comprise additional agriculturally active compounds (i.e., in addition to the (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide contained in WDG). Additionally or alternatively, WDG may be used in combination with one or more agriculturally active compounds, typically as part of an agricultural composition for application to crops, seeds that may be sown to produce crops, harvested produce, and / or soil in which crops have been or may be planted or sown. The agricultural composition may be a particulate suspension composition formed, at least in part, by combining the disclosed WDG (or a formulation thereof) with a suitable solvent or solvent mixture, such as (but not limited to) water.

[0065] The disclosed WDG embodiments are useful for enhancing the effectiveness of a variety of agriculturally active compounds, including fungicides, antivirals, antibacterials, herbicides, insecticides / acaricides, molluscicides, nematicides, repellents, plant control agents, plant regulators, synergists, fertilizers, and soil conditioners.

[0066] In one embodiment, the presently disclosed WDG is useful for enhancing the germicidal effect of various germicides. Germicidal agents for use with the disclosed WDG may 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]

[0067] Fungicides are more extensively catalogued by the Fungicide Resistance Action Committee (FRAC) in the FRAC Code List 2022, reproduced in Appendix 1, which is incorporated herein by reference in its entirety.

[0068] In one embodiment, the disclosed WDG is used in combination with one or more compounds from a family or group set forth in Table 2, Appendix 1, or both. In certain embodiments, the WDG is used in combination with one or more fungicides listed in column 1 of Table 1.

[0069] In certain embodiments, the disclosed WDG is selected from the group consisting of benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyanilide fungicides, carboxamide fungicides, phenylamide fungicides, phosphonate fungicides, cinnamate fungicides, oxysterol binding protein inhibitor (OSBPI) fungicides, triazole carboxamide fungicides, carbamate fungicides, Group 27 fungicides, benzamide fungicides, demethylation-inhibiting piperazine fungicides, demethylation-inhibiting pyrimidine fungicides, and demethylation-inhibiting pyrimidine fungicides. In combination with one or more fungicides selected from an inhibiting azole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper ammonium complex 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 QiI fungicide, a guanidine fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0070] Specific fungicides that may be enhanced by use in combination with the WDGs disclosed in accordance with the methods herein include benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthion, Opyrad, 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, mefentri Fluconazole, metconazole, ipconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclo These may include strobin, 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.

[0071] In some embodiments, combined treatment with a selected fungicide and the disclosed WDG provides synergistic fungicidal activity against plant pathogenic fungi.

[0072] In some embodiments, the present disclosure provides compositions and methods for treating plants or plant seeds infected or at risk of infection with fungal pathogens. In some such embodiments, the disclosed compositions include a fungicide formulation, the disclosed WDG, and a botanically acceptable carrier. In another embodiment, the fungicide and WDG are administered in separate compositions. In a further embodiment, an agricultural or horticultural fungicide is used in combination with other compounds in addition to the disclosed WDG. Such other compounds may be administered in the same or separate compositions as the fungicide and / or WDG. Examples of other ingredients include known carriers used to formulate the formulation. Additional examples include herbicides, insecticides / acaricides, nematicides, soil pesticides, plant control agents, synergists, fertilizers, soil conditioners, and animal feeds known in the art. In one embodiment, the inclusion of such other ingredients provides a synergistic effect on crop growth.

[0073] In certain embodiments, the disclosed WDG is used to enhance the effectiveness of herbicides. Exemplary herbicides for use in combination with the formulation are known to those skilled 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 WDGs include, but are not limited to, 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, lycopene cyclase inhibitors, and combinations thereof.

[0074] In some embodiments, the disclosed WDGs are used to enhance the effectiveness of insecticides. Exemplary insecticides for use in combination with the disclosed WDGs are known to those of skill in the art and include, without limitation, those listed in Appendix 3.

[0075] III. Method An embodiment of a method of using the disclosed WDG combines the WDG (or a formulation and / or agricultural composition thereof) with a solvent such as water to form an agricultural composition suitable for application to a plant, a plant part, the soil in which the plant is growing or will grow, or the soil in which the seeds have been or will be sown. The method may further include applying the agricultural 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 seeds have been or will be sown.

[0076] In some embodiments, the disclosed agricultural compositions include one or more agriculturally active compounds, and the agricultural composition is formed by diluting the agricultural composition with a suitable solvent, such as water, to a concentration suitable for agricultural use. Optionally, one or more additional agriculturally active compounds can be added before, during, and / or after adding water to the agricultural composition. In some embodiments, WDG can be formulated to include agriculturally active compounds.

[0077] In certain embodiments, the WDG does not include any agriculturally active compounds, and the agricultural composition is formed by combining the WDG with a suitable solvent, such as water, to obtain a concentration suitable for agricultural use. In such embodiments, forming the agricultural composition can further include adding one or more agriculturally active compounds to the water before the WDG is added, at the same time as the WDG is combined with the water, and / or to the aqueous mixture containing the WDG at a later time.

[0078] In certain non-limiting embodiments, the disclosed WDG is combined with water to obtain a composition suitable for agricultural use in an amount sufficient to provide a first active compound in an amount ranging from 0.01% to 80% by weight in the final composition, or from 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 in the final composition. In one embodiment, the first active compound is provided in an amount ranging from 0.01% to 50%, e.g., 15% to 50%, 20% to 45%, 25% to 40%, e.g., 0.01, 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% by volume in the final composition comprising WDG and water.

[0079] 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 WDG disclosed herein, for example, in the absence of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0080] In some embodiments, a method of making an agricultural composition includes adding a WDG disclosed herein to water 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 WDG, for example, in the absence of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide. One of ordinary skill in the art will understand that the disclosed WDG and the agriculturally active compound can be added to water sequentially in any order or substantially simultaneously to form the agricultural composition.

[0081] In any embodiment, the one or more agriculturally active compounds is a fungicide, repellent, herbicide, insecticide, molluscicide, nematicide, or combination thereof disclosed herein.

[0082] Also disclosed herein are method embodiments for controlling or preventing fungal growth. The methods can include applying an agricultural composition described herein to a plant, a part of a plant, the soil in which a plant is growing or will grow, or the soil in which seeds have been or will be sown.

[0083] 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.

[0084] Agronomic compositions comprising the disclosed WDGs can be applied to plant parts such as leaves, stems, stems, flowers, buds, fruits, seeds, shoots, roots, tubers, tuberous roots, shoots, or stumps. The WDGs (including their formulations and agronomic compositions) can also be applied to improved varieties / varieties, cultivars, and mutant, hybrid, and genetically modified embodiments of these plants.

[0085] The disclosed agricultural compositions containing WDG can be used for seed treatment, foliage application, soil application, or water application to control a variety of diseases occurring in agricultural or horticultural crops, including flowers, turf, and pasture grasses.

[0086] Agricultural compositions containing the disclosed WDG are useful for enhancing the effectiveness of antimicrobial agents, for example, the disclosed WDG can be used in combination with antimicrobial agents to combat bacterial and viral infections.

[0087] Embodiments of the disclosed WDGs are useful for enhancing the effectiveness of herbicides, for example, the disclosed WDGs can be used in combination with one or more herbicides to control weeds or other unwanted vegetation.

[0088] Embodiments of the disclosed WDGs are useful for enhancing the effectiveness of insecticides, for example, the disclosed WDGs can be used in combination with one or more insecticides to control insect infestations.

[0089] Embodiments of the disclosed WDGs are useful for enhancing the effectiveness of acaricides or miticides, for example, the disclosed WDGs can be used in combination with one or more acaricides to control mites.

[0090] Embodiments of the disclosed WDGs are useful for enhancing the effectiveness of molluscicides. For example, the disclosed WDGs can be used in combination with one or more molluscicides to prevent slug or snail damage to crops.

[0091] The disclosed WDG embodiments are useful for enhancing the effectiveness of nematicides. For example, the disclosed WDGs can be used in combination with one or more nematicides to prevent nematodes from interfering with crops.

[0092] The disclosed WDG embodiments 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.

[0093] Botrytis cinerea is an airborne plant pathogen whose necrotrophic lifestyle affects 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 failed to control Botrytis cinerea due to its genetic plasticity.

[0094] The genus Colletotrichum consists of approximately 600 species that infect 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).

[0095] 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).

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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 that resemble the galls of common smut.

[0100] Examples of crops that may be treated and plant diseases (pathogens) that may be controlled using the compounds and compositions of the present disclosure include, but are not limited to: Beets: Cercospora leaf spot (Cercospora beticola), black root rot (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc.

[0101] Peanuts: Brown leaf spot (Mycosphaerella arachidis), leaf spot (Ascochyta sp.), rust (Puccinia arachidis), damping-off (Pythium debaryanum), Alternaria leaf spot (Alternaria alternata), stem rot (Sclerotium rolfsii), black rust (Mycosphaerella berkeleyi), etc.

[0102] Cucumbers: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), gummy stem blight (Mycosphaerella melonis), wilt (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), Cladosporium leaf spot (Cladosporium cucumerinum), Corynespora leaf spot (Corynespora cassiicola), damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial leaf spot (Pseudomonas syringae pv. Lechrymans), etc.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] Onion: Neck rot (Botrytis allii), gray mold (Botrytis cinerea), leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor), Phytophthora porn, etc.

[0107] Cabbage: Clubroot disease (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. campestris), bacterial black spot (Pseudomonas syringae pv. Maculicola, Pspv. alisalensis), dew blight (Peronospora parasitica), sclerotinia rot (Sclerotinia sclerotiorum), black spot (Alternaria brassicicola), gray mold (Botrytis cinerea), etc.

[0108] Common legumes: Sclerotinia rot (Sclerotinia sclerotiorum), grey mould (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot (Phaeoisariopsis griseola), etc.

[0109] 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.

[0110] Apricot: Red mold (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), etc.

[0111] Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), etc.

[0112] Peaches: Brown rot (Monilinia fructicola), red mold disease (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), bacterial shot hole disease (Xanthomonas campestris pv.pruni), etc.

[0113] Almonds: Brown rot (Monilinia taxa), spot blotch (Stigmina carpophila), red mold (Cladosporium carpophilum), red leaf spot (Polystigma rubrum), alternaria blotch (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc.

[0114] Yellow peach: Brown rot (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Monilinia kusanoi disease (Monilinia kusanoi), etc.

[0115] 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.

[0116] 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.

[0117] Tea: Ring spot disease (Pestalotiopsis longiseta, P. theae), anthracnose disease (Colletotrichum theae-sinensis), net cake disease (Exobasidium reticulatum), etc.

[0118] 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.

[0119] Wheat: powdery mildew (Blumeria graminis f.sp.tritici), head blight (Gibberella zeae), brown rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), Septoria nodorum blotch (Leptosphaeria nodorum), pink snow mold (Typhula incarnata), large snow mold (Myriosclerotinia borealis), take-all (Gaeumannomyces graminis), ergot (Claviceps purpurea), common bunt (Tilletia caries), stinking bunt (Telletia caries), loose smut (Ustilago nuda), etc.

[0120] Barley: leaf spot (Pyrenophora graminea), net blotch (Pyrenophora teres), scald (Rhynchosporium secalis), covered smut (Ustilago tritici, U.nuda), etc.

[0121] 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.

[0122] Tobacco: Sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum), Phytophthora rot (Phytophthora nicotianae), etc.

[0123] Tulips: Gray mold (Botrytis cinerea), etc.

[0124] Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia rot (Sclerotinia sclerotiorum), etc.

[0125] 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.

[0126] Orchard grass: Powdery mildew (Erysiphe graminis), etc.

[0127] 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.

[0128] Potatoes: phytophthora infestans, early blight (Alternaria solani), scarf disease (Thanaphorus cucumeris), Verticillium wilt (Verticillium albo-atrum, V. dahlia, V. nigrescens, etc.).

[0129] Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc.

[0130] Rapeseed: Sclerotinia rot (Sclerotinia sclerotiorum), root rot (Phoma lingam), black spot (Alternaria brassicae), etc.

[0131] Coffee: Rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), leaf spot (Cercospora coffeicola), etc.

[0132] Sugarcane: Brown rust (Puccinia melanocephala), etc.

[0133] 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.

[0134] Cotton: Seedling damping-off (Pythium sp.), rust (Phakopsora gossypii), sour rot (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.

[0135] IV. Process The disclosed WDG can be made by combining a first agriculturally active compound according to the present disclosure with a dispersant and, optionally, a dust suppressant. In certain embodiments, the WDG is made by combining particles of the first agriculturally active compound with a dispersant to obtain granules formed from a matrix containing the first agriculturally active compound and the dispersant. In certain embodiments, the particles of the first agriculturally active compound are milled and then blended with other optional ingredients, such as a dispersant, followed by granulation of the resulting mixture to obtain porous granules. In some other embodiments, the particles of the first agriculturally active compound are milled and granulated while bound together and coated by the dispersant to form porous granules.

[0136] In some embodiments, the method includes providing a first agriculturally active compound, a dispersant, and optionally a dust control agent, and forming a WDG. Optionally, a binder, an inert carrier, a diluent, and / or the agriculturally active compound may be added. In some embodiments, the first agriculturally active compound is milled to a desired particle size, such as those described herein. A specific particle size or particle size range for the granule formulation can be achieved by milling in aqueous suspension prior to granulation, or alternatively by methods such as air-jet milling or other methods known to those skilled in the art of such formulations. The first agriculturally active compound can then be granulated with a dispersant. In some embodiments, the first agriculturally active compound is granulated simultaneously with the addition of a dispersant, followed by the addition of a dust control agent. In yet other embodiments, the first agriculturally active compound is combined with a dispersant, the mixture is granulated, and then combined with the dust control agent. Optional ingredients may be added at any time during the preparation of the WDG. Any carrier or diluent present may be combined with the first agriculturally active compound before carrying out the granulation process, and the method of combination may be any one of several methods known to those skilled in the art, such as ribbon blending or milling the ingredients together. Any dispersant and optional binder present may be combined with the first agriculturally active compound before carrying out the granulation process, or may be added during the granulation process. If added before granulation, the addition may be carried out by any one of several methods known to those skilled in the art, such as adding a solution or powder during or before ribbon blending or kneading. If added during granulation, the addition is usually carried out by spraying or pouring a solution of the binder. Those skilled in the art will understand that the dispersant and dust suppressant, as well as optional ingredients such as inert carriers, diluents, and / or agriculturally active compounds, may be added in any suitable or convenient order.

[0137] The granulation process may be carried out by one of several methods known to those skilled in the art, such as extrusion, fluidized bed granulation, or pan granulation. The details of the order of ingredient addition can be varied as described above and conveniently, but those skilled in the art will understand that fluidized bed granulation proceeds with the addition of water or solvent and the subsequent evaporation of at least a portion of the water or solvent during the fluidized bed process. Those skilled in the art will also understand that extrusion and pan granulation result in the formation of granules containing the water or solvent used in the granulation process, and that these granules require a subsequent drying step.

[0138] V. Overview of the Embodiment As used herein, the structure [ka] Disclosed are embodiments of water-dispersible granules comprising particles of a first agriculturally active compound having the formula:

[0139] In any or all embodiments, the particles of the first agriculturally active compound are present in an amount ranging from 5% to 90% by weight.

[0140] In any or all embodiments, the dedusting agent is present in an amount ranging from 0.5% to 15% by weight.

[0141] In any or all embodiments, the dedusting agent is present in an amount ranging from 1% to 30% by weight.

[0142] In any or all embodiments, the particles of the first agriculturally active compound are present in an amount ranging from 30% to 85% by weight.

[0143] In any or all embodiments, the particles of the first agriculturally active compound are present in an amount ranging from 30% to 40% by weight.

[0144] In any or all embodiments, the particles of the first agriculturally active compound are present in an amount ranging from 70% to 85% by weight.

[0145] In any or all embodiments, the dedusting agent is a liquid or a low melting point solid.

[0146] In any or all embodiments, the dust suppressant is selected from a surfactant, a wax, a natural oil, a chemically modified natural oil, a low volatility organic solvent, or a combination thereof.

[0147] In any or all embodiments, the dispersant is a high molecular weight dispersant.

[0148] In any or all embodiments, the dispersant has a molecular weight ranging from 400 Daltons to 2,000,000 Daltons.

[0149] 400 Daltons to 2,000,000 Daltons In embodiments, the dispersant has a molecular weight in the range of 1,000 Daltons to 100,000 Daltons.

[0150] In any or all embodiments, the dispersant is an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof.

[0151] In any or all embodiments, the dispersant is an anionic dispersant.

[0152] In any or all embodiments, the dispersant is a non-ionic dispersant.

[0153] In any or all embodiments, the dispersant is selected from a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof.

[0154] In any or all embodiments, the dispersing agent 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 combinations thereof.

[0155] In any or all embodiments, the dedusting agent is present in an amount ranging from 3% to 20% by weight.

[0156] In any or all embodiments, the water-dispersible granules further comprise a binder.

[0157] In any or all embodiments, the binder is present in an amount ranging from 5% to 30% by weight.

[0158] In any or all embodiments, the binder is present in an amount ranging from 10% to 25% by weight.

[0159] In any or all embodiments, the water-dispersible granules comprise a binder selected from compounds that have a melting point above 100° C. and that dissolve completely in water during the granulation process.

[0160] In any or all embodiments, the water-dispersible granules include one or more inert carriers, diluents, or combinations thereof.

[0161] In any or all embodiments, the inert carrier or diluent is present in an amount sufficient to make up the total weight balance of the water-dispersible granules to 100% by weight.

[0162] In any or all embodiments, the inert carrier or diluent is selected from starch, wood flour, cellulose, chemically modified cellulose, or mineral materials.

[0163] In any or all embodiments, the mineral material is selected from clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, or combinations thereof.

[0164] In any or all embodiments, the water-dispersible granules further comprise an antifoaming agent.

[0165] In any or all embodiments, the antifoaming agent is an emulsion of silicone oil.

[0166] In any or all embodiments, the antifoaming agent is present in an amount ranging from 0.01% to 1% by weight.

[0167] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 10 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0168] In any or all embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of about 1 micron or less to about 15 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0169] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of about 1 micron to about 15 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0170] In any or all embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of about 1 micron to about 7 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0171] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 5 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0172] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 2 microns as measured by light scattering after dilution and dispersion in water of the WDG.

[0173] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size of about 15 microns or less as measured by light scattering after dilution and dispersion in water of the WDG.

[0174] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size of about 7 microns or less as measured by light scattering after dilution and dispersion in water of the WDG.

[0175] In any or all of the embodiments, the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size of about 1 micron as measured by light scattering after dilution and dispersion in water of the WDG.

[0176] In any or all embodiments, the water-dispersible granules comprise: (a) Structure [ka] particles of a first agriculturally active compound having the formula: (b) 0.5 wt. % to 15 wt. % of a dust suppressant selected from a surfactant, a wax, a natural oil, a chemically modified natural oil, a low-volatility organic solvent, or a combination thereof; (c) 3% to 20% by weight of a high molecular weight dispersant; The particles of the first agriculturally active compound have a volume weighted median particle size of less than 2 microns.

[0177] Also disclosed herein are compositions comprising water-dispersible granules according to any or all of the above embodiments, and additional agriculturally active compound embodiments.

[0178] In any or all embodiments, the additional agriculturally active compound is a fungicide, a repellent, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

[0179] In any or all embodiments, the additional 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a demethylation-inhibiting pyrim ... The fungicide is selected from a fungicide, a demethylation inhibitor azole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper ammonium complex 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 QoI fungicide, a QiI fungicide, a guanidine fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0180] In any or all embodiments, 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, The fungicide is selected from ipconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, 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 a combination thereof.

[0181] In any or all embodiments, the composition further comprises water.

[0182] In any or all embodiments, the water-dispersible granules are present in the composition in an amount sufficient to enhance the biological effect of the additional agriculturally active compound such that the total amount of the additional agriculturally active compound in the composition applied to the crop or produce is lower than would typically be required and / or recommended to produce the same biological effect in a composition that does not include the water-dispersible granules.

[0183] In any or all embodiments, the additional agriculturally active compound is a fungicide, a repellent, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

[0184] In any or all embodiments, the additional 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a demethylation-inhibiting pyrim ... The fungicide is selected from a fungicide, a demethylation inhibitor azole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper ammonium complex 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 QoI fungicide, a QiI fungicide, a guanidine fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0185] In any or all embodiments, the additional agriculturally active compound may be benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen, solate Nol (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 The fungicide is selected from benzophenone, ipconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, 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 a combination thereof.

[0186] Also disclosed herein are methods of using a composition according to any or all of the above embodiments, comprising applying the composition to a plant, a part of a plant, soil in which a plant is growing or will grow, or soil in which seeds have been or will be sown.

[0187] Also disclosed herein are methods of controlling or preventing fungal growth, comprising applying a composition according to any or all of the above embodiments to an area having fungal growth or at risk of developing fungal growth.

[0188] Also disclosed herein are embodiments of a method of controlling or preventing fungal growth comprising combining a composition according to any or all of the above embodiments with water to form a particulate suspension comprising particles of a first agriculturally active compound, and applying the particulate suspension to a site having fungal growth or at risk of developing fungal growth.

[0189] In any or all embodiments, the method further comprises combining the water-dispersible granules with an additional agriculturally active compound to form a composition.

[0190] In any or all embodiments, combining the water-dispersible granules with the agriculturally active compound comprises adding an amount of the agriculturally active compound to the water-dispersible granules that is less than the amount of the agriculturally active compound recommended for use in the absence of the water-dispersible granules.

[0191] Also disclosed herein are embodiments of methods for making a dispersion comprising water-dispersible granules according to any or all of the above embodiments, the method comprising combining the water-dispersible granules with water and an additional agriculturally active compound to obtain a mixture, wherein the water-dispersible granules and the additional agriculturally active compound are each present in a concentration sufficient to provide a biological effect when the mixture is applied to a crop or produce.

[0192] In any or all embodiments, the concentration of the water-dispersible granules in the mixture ranges from 0.01% to 10% by weight.

[0193] In any or all embodiments, the method further comprises adding an adjuvant to the mixture.

[0194] In any or all embodiments, the additional agriculturally active compound is selected from a miticide, a fungicide, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

[0195] In any or all embodiments, the additional 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation inhibiting piperazine fungicide, a demethylation The fungicide is selected from an inhibited pyrimidine fungicide, a demethylation inhibited azole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper ammonium complex 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 QiI fungicide, a guanidine fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

[0196] In any or all embodiments, the additional agriculturally active compound may be benomyl, thiabendazole, thiophanate methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, fenpyrazamine, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, impirfluxam, isofetamide, oxycarboxin, penthiopyrad, pydiflumetofen, solatenofen Benzovindiflupyr, mefenoxam, metalaxyl, oxadixyl, aluminum tris, phosphorous acid, dimethomorph, mandipropamide, oxathiapiproline, ethaboxam, cymoxanil, propamocarb, fluopicolide, triforine, lenarimol, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flutriafol, mefentrifluconazole , metconazole, ipconazole, myclobutanil, propiconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, piperalin, spiroxamine, cyflufenamid, metrafenone, pyriophenone, azoxystrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, mandestrobin, picoxystrobin, pyraclostrobin, The active ingredient is selected from vin, 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 a combination thereof. [Example]

[0197] VI. Working Examples Example 1 Preparation of stable and effective granules by extrusion A sufficient amount of the first active compound is air-milled to obtain at least 100 g of material with a median particle size of less than 1.5 microns as measured by a Malvern Mastersizer 3000. 40 g of this powder is combined with 25 g of Tamol SN, which functions as a dispersant and binder, 1 g of Surfonic L24-7 dust suppressant surfactant, 34 g of starch powder as an inert filler, and 0.1 g of SAG 1572 antifoaming agent. This composition is mixed with 50 g of water in a planetary mixer to obtain a thick paste. The paste is extruded through a sieve with 1 mm openings to obtain granules, which are dried overnight in a vacuum oven at 60°C. Subsamples are stored at several different temperatures and periodically evaluated for pH, appearance, dispersibility, and suspension stability. The formulation is expected to have excellent handling characteristics, excellent physical stability, and biological efficacy comparable to aqueous suspensions with similarly sized particles of the first active compound.

[0198] Example 2 Preparation of stable and effective granules by pan granulation 40 g of the first active compound was milled as described above to a particle size of less than 1.5 microns median diameter and combined in a ribbon blender with 25 g of Tamol SN as a dispersant and binder, 34 g of Celite 545 diatomaceous earth as an inert filler, and 1 g of Surfonic L24-7 as a dust suppressant surfactant. The powder was placed in a rotating tilted flat-bottom pan and sprayed with water to form granules, which were then dried overnight in a vacuum oven at 60°C. Subsamples were stored at several different temperatures and periodically evaluated for pH, appearance, dispersibility, and suspension stability. The formulation was expected to have excellent physical stability, handling characteristics, and biological efficacy comparable to aqueous suspensions with similarly sized particles of the first active compound.

[0199] Example 3 Preparation of stable and effective granules by fluidized bed granulation 255 g of the first active compound was milled as described above to obtain a particle size of less than 1.5 microns in median diameter and placed in the chamber of a fluidized bed granulator. Fluidization was performed at an inlet air temperature of 70°C. 15 g of dispersant and binder Tamol SN and 15 g of binder Star-Dri 15 were sprayed into the chamber as an aqueous solution containing 40% total solids by weight, followed by sufficient water to produce an acceptable granule. The air flow was then continued to evaporate the water, after which 15 g of dust suppressant surfactant Surfonic L24-7 was sprayed into the chamber. Subsamples were stored at several different temperatures and periodically evaluated for pH, appearance, dispersibility, and suspension stability. The formulation was expected to have excellent handling characteristics, excellent physical stability, and biological efficacy comparable to aqueous suspensions with similarly sized particles of the first active compound.

[0200] Example 4 Effectiveness as a function of granularity Method: Three different aqueous suspension concentrates were prepared using 30% NGXT-1915 (2.5 wt.% tristyrylphenol ethoxylate surfactant, 2.0 wt.% ethylene oxide-propylene oxide block copolymer dispersant, 5.0 wt.% propylene glycol cryoprotectant, 0.1 wt.% silicone oil antifoamant, and 52.4% distilled water). After milling, 8.0 wt.% viscosity modifier gel containing 2.0% xanthan and 1.0% biocide in water was added. The milling conditions were controlled to achieve various particle sizes for the three samples. Specifically, milling was performed using ceramic grinding media in a water-jacketed agitator vessel for various milling times. Samples were diluted with water and bioassayed in greenhouses using NGXT-1915 at 20 ppm in combination with one of the commercial fungicides, Amistar (0.03 L / ha), Imtrex (0.35 L / ha), Proline (0.125 L / ha), or Baraya (0.2 L / ha). Each combination was used to challenge four commercially important pathogenic fungi: Botrytis cinerea (on tomato plants), Zymoseptoria tritici (on wheat plants), Puccinia triticina (on wheat plants), and Phakopsora pachyrhizi (on soybean cultivar Siverka). Petersfield horticultural compost (75% medium peat, 12% sieved sterilized loam, 3% medium vermiculite, 10% granular (sieved to 5mm, no lime), 1.5kg PG mix per m³, lime added to pH 5.5-6.0, wetting agent (Vitax Ultrawet Seeds were sown 1-2 cm deep in 9 cm diameter pots using 200 ml of water per m³ and germinated / grown at 23°C under 16 hours of day / 8 hours of overnight light. Plants were treated 2-3 weeks after sowing when they were at the BBCH11 growth stage (the first pair of true leaves (single leaves) had developed). Using a track sprayer, plants were treated with commercial fungicides and NGXT-1915 using a water volume of 200 L / ha. 24 hours after treatment, plants were inoculated with the appropriate fungus (pathogen). Four replicates were used for each fungicide, pathogen, and formulation combination.When disease symptoms were fully manifested, 7–20 days (depending on the pathogen), each plant was evaluated for percent disease control. Appropriate controls, including "inoculated checks," were used in all experiments; plants were inoculated with a specific pathogen and assessed for disease levels. Each commercial fungicide was also tested alone as part of each treatment; this served as the "control" standard against which experimental compounds were evaluated. Percent disease control for each treated plant was calculated as the average disease severity of inoculated but untreated plants ("check") minus the average disease severity of treated plants, divided by the "check." Percent synergy for each formulation plus fungicide combination (test combination) was calculated as the disease control of plants treated with fungicide alone ("control") minus the disease control of the test combination, divided by 100% minus the "control." Synergy represents the amount of benefit achieved by adding the NGXT-1915 formulation to a fungicide and is expressed as a percentage of the maximum possible effect. Thus, 100% means complete disease control and 0% means the combination had no effect.

[0201] result: The particle sizes of the ground samples were measured using a laser light scattering instrument, and the volume weighted median particle sizes were 1.0, 7.0, and 15 microns, respectively. For simplicity, these samples will be referred to as A1, B7, and C15 in the following discussion.

[0202] Zymoseptoria tritici: There was no consistent synergy with Amistar; with Imtrex, synergy was 28%, 28%, and 4.6% for A1, B7, and C15, respectively; with Proline, synergy was 26%, 25%, and 61% for A1, B7, and C15, respectively; and with Balaya, synergy was 51%, 40%, and 36% for A1, B7, and C15, respectively.

[0203] Phakopsora pachyrhizi: With Amistar the synergy was 30% for A1, no synergy for B7 or C15, with Imtrex and Proline there was no significant synergy, and with Balaya it was 40%, 33%, and 20% for A1, B7, and C15, respectively.

[0204] There was no significant synergy with Puccinia triticina:Amistar, 29%, 3%, and no synergy with Imtrex for A1, B7, and C15, respectively, and no significant synergy with Proline or Balaya.

[0205] Botrytis cinerea: There was no significant synergy with Amistar, 18%, 6%, and no synergy with Imtrex for A1, B7, and C15, respectively, Proline had synergy of 33%, 14%, and 10% for A1, B7, and C15, respectively, and Balaya had no significant synergy.

[0206] Conclusion: The composition of the suspension concentrate samples was selected to achieve minimum physical properties suitable for greenhouse assays. These ingredients ensured efficient spray deposition and leaf coverage, allowing for evaluation of the effect of particle size on biological efficacy. In this case, the particles were not formulated into a water-dispersible granule format; however, it would be routine for those skilled in the art to perform this formulation without altering particle size or biological efficacy. Therefore, we conclude that the findings regarding particle size apply to water-dispersible granules. The specific method used in this example to control particle size can be used directly to obtain specific particles for granule formulations by milling in aqueous suspension prior to granulation, or by using alternative methods such as air-jet milling, without changing the conclusion that particle size has a surprising effect on biological efficacy.

[0207] If there is a synergistic effect, and the results are grouped by fungicide, the following can be highlighted: a) In combination with Imtrex, B7 is always superior to C15, and A1 is either essentially identical to B7 (one case) or superior to B7 (three cases) (i.e., A1 > B7 > C15). b) In combination with Balaya, B7>C15. c) In combination with Amistar, there is a synergistic effect only against Phakopsora pachyrhizus, and here too there is a clear trend of A1>B7>C15. d) In combination with Proline, in one case A1>B7>C15, and in another case C15>A1=B7.

[0208] If there is a synergistic effect, and instead the results are grouped by pathogen, the following can be highlighted: a) Against Zymoseptoria tritici, A1=B7>C15 for Imtrex, C15>A1=B7 for Proline, and A1>B7>C15 for Balaya. b) Against Phakopsora pachyrhizi, only A1 had a synergistic effect in Amistar, whereas A1 > B7 > C15 in Balaya. c) Against Puccinia triticina, A1>B7>C15 for Imtrex. d) Against Botrytis cinerea, A1>B7>C15 for both Imtrex and Proline

[0209] Within this set of experiments, there is one clear counterexample of Proline against Zymoseptoria tritici (based on a possible outlier in C15), but the other seven examples establish a pattern. Overall, suspension concentrates with a median particle size of 1 micron are more biologically effective than suspension concentrates with a median particle size of 7 microns, which in turn are more biologically effective than suspension concentrates with a median particle size of 15 microns. This pattern is valid for all pathogens tested here. Of the fungicides tested, effectiveness is most consistent with Imtrex and Balaya, although there are examples with other fungicides as well.

[0210] The inventors further conclude that in water-dispersible granule formulations, a median particle size of about 1 micron (in this case, and when measured after dispersion in water suitable for spray application) results in higher biological effectiveness than a median particle size of about 7 microns, which in turn results in higher biological effectiveness than a median particle size of about 15 microns. [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

[0211] In view of the many possible embodiments to which the principles of this disclosure may be applied, it should be recognized that the illustrated embodiments are preferred examples only and should not be construed as limiting the scope of the disclosure. Rather, the scope is defined by the following claims. The inventors therefore claim as their invention all that comes within the spirit and scope of these claims.

Claims

1. A water-dispersible granule comprising: structure 【Transformation 6】 particles of a first agriculturally active compound having a dispersant, The water-dispersible granules, wherein the particles of the first active compound have a volume weighted median particle size ranging from greater than 0.01 microns to 20 microns.

2. 10. The water-dispersible granules of claim 1, further comprising a dust suppressant.

3. 10. The water-dispersible granule of claim 1, wherein said particles of said first agriculturally active compound are present in an amount ranging from 5% to 90% by weight.

4. 3. The water-dispersible granules of claim 2, wherein the dust suppressant is present in an amount ranging from 0.5% to 15% by weight.

5. A water-dispersible granule according to any one of claims 1 to 4, wherein the dispersant is present in an amount ranging from 1% to 30% by weight.

6. 6. The water-dispersible granule of any one of claims 1 to 5, wherein said particles of said first agriculturally active compound are present in an amount ranging from 30% to 85% by weight.

7. 7. The water-dispersible granule of claim 6, wherein said particles of said first agriculturally active compound are present in an amount ranging from 30% to 40% by weight.

8. 7. The water-dispersible granule of claim 6, wherein said particles of said first agriculturally active compound are present in an amount ranging from 70% to 85% by weight.

9. The water-dispersible granule according to any one of claims 2 to 8, wherein the dust-proofing agent is a liquid or a low-melting-point solid.

10. 10. The water-dispersible granule according to any one of claims 2 to 9, wherein the dust suppressant is selected from a surfactant, a wax, a natural oil, a chemically modified natural oil, a low-volatility organic solvent, or a combination thereof.

11. 11. The water-dispersible granules according to any one of claims 1 to 10, wherein the dispersant is a high molecular weight dispersant.

12. 12. A water-dispersible granule according to any one of claims 1 to 11, wherein the dispersant has a molecular weight in the range of 400 Daltons to 2,000,000 Daltons.

13. 13. The water-dispersible granules according to any one of claims 1 to 12, wherein the dispersant has a molecular weight in the range of 1,000 to 100,000 daltons.

14. 14. The water-dispersible granules according to any one of claims 1 to 13, wherein the dispersant is an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof.

15. 15. The water-dispersible granules of claim 14, wherein the dispersant is an anionic dispersant.

16. 15. The water-dispersible granules of claim 14, wherein the dispersant is a non-ionic dispersant.

17. 15. The water-dispersible granules of any one of claims 1 to 14, wherein the dispersant is selected from homopolymer dispersants, random or statistical copolymers, block copolymers, or combinations thereof.

18. 15. The water-dispersible granules of any one of claims 1 to 14, wherein the dispersing agent 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.

19. 19. Water-dispersible granules according to any one of claims 1 to 18, wherein the dispersant is present in an amount ranging from 3% to 20% by weight.

20. 20. The water-dispersible granule according to any one of claims 1 to 19, further comprising a binder.

21. 21. The water-dispersible granules of claim 20, wherein the binder is present in an amount of from 5% to 30% by weight.

22. 22. Water-dispersible granules according to claim 20 or 21, wherein the binder is present in an amount of from 10% to 25% by weight.

23. 23. Water-dispersible granules according to any one of claims 20 to 22, wherein the binder is selected from compounds having a melting point above 100°C and which dissolve completely in water during the granulation process.

24. The water-dispersible granules of any one of claims 1 to 23, further comprising one or more inert carriers, diluents, or combinations thereof.

25. 25. The water-dispersible granule of claim 24, wherein the inert carrier or diluent is present in an amount sufficient to make up the total weight balance of the water-dispersible granule to 100% by weight.

26. 26. Water-dispersible granules according to claim 24 or 25, wherein the inert carrier or diluent is selected from starch, wood flour, cellulose, chemically modified cellulose, or mineral materials.

27. 27. The water-dispersible granules of claim 26, wherein the mineral material is selected from clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, or combinations thereof.

28. 28. The water-dispersible granules according to any one of claims 1 to 27, further comprising an antifoaming agent.

29. 29. The water-dispersible granules of claim 28, wherein the antifoaming agent is an emulsion of silicone oil.

30. 29. The water-dispersible granules of claim 28, wherein the antifoaming agent is present in an amount ranging from 0.01% to 1% by weight.

31. 28. The water-dispersible granule of any one of claims 1 to 27, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of from greater than 0.01 microns to about 15 microns as measured by light scattering after dilution and dispersion in water of the WDG.

32. 28. The water-dispersible granule of any one of claims 1 to 27, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 10 microns as measured by light scattering after dilution and dispersion in water of the WDG.

33. 28. The water-dispersible granule of any one of claims 1 to 27, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size of less than about 7 microns as measured by light scattering after dilution and dispersion of the WDG in water.

34. 28. The water-dispersible granule of any one of claims 1 to 27, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 5 microns as measured by light scattering after dilution and dispersion in water of the WDG.

35. 32. The water-dispersible granule of claim 31, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size in the range of greater than 0.01 microns to 2 microns as measured by light scattering after dilution and dispersion in water of the WDG.

36. 28. The water-dispersible granule of any one of claims 1 to 27, wherein the particles of the first agriculturally active compound are milled prior to granulation so that the particles have a volume weighted median particle size of about 1 micron as measured by light scattering after dilution and dispersion in water of the WDG.

37. A water-dispersible granule comprising: (a) Structure 【Transformation 7】 particles of a first agriculturally active compound having the formula: (b) 3% to 20% by weight of a high molecular weight dispersant; The water-dispersible granules wherein the particles of the first agriculturally active compound have a volume-weighted median particle size of less than 2 microns.

38. 38. The water-dispersible granule of claim 37, further comprising 0.5% to 15% by weight of a dust suppressant selected from a surfactant, a wax, a natural oil, a chemically modified natural oil, a low-volatility organic solvent, or a combination thereof.

39. 39. The water-dispersible granules of claim 37 or claim 38, having a volume weighted median particle size of about 1 micron as measured by light scattering after dilution and dispersion of the WDG in water.

40. 1. A composition comprising: A water-dispersible granule according to any one of claims 1 to 34, and an additional agriculturally active compound.

41. 41. The composition of claim 40, wherein the additional agriculturally active compound is a fungicide, a repellent, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

42. The additional agriculturally active compound is selected from the group consisting of 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a demethylation-inhibiting pyrimidine fungicide, a demethylation-inhibiting azole fungicide, and a hydroxyanilide fungicide.

42. The composition of claim 40 or 41, wherein the fungicide is selected from the group consisting of fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, strobilin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, QiI fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

43. The agriculturally active compound is 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), 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 43. The composition of any one of claims 40 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, 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, flutianil, or a combination thereof.

44. The composition of any one of claims 40 to 43, further comprising water.

45. 45. The composition of claim 44, wherein the water-dispersible granules are present in the composition in an amount sufficient to enhance the biological effect of the additional agriculturally active compound such that the total amount of the additional agriculturally active compound in the composition applied to a crop or agricultural product is lower than would typically be required and / or recommended to produce the same biological effect in a composition that does not include the water-dispersible granules.

46. 46. ​​The composition of claim 45, wherein the additional agriculturally active compound is a fungicide, a repellent, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

47. The additional agriculturally active compound is selected from the group consisting of 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a demethylation-inhibiting pyrimidine fungicide, a demethylation-inhibiting azole fungicide, and a hydroxyanilide fungicide.

47. The composition of claim 45 or 46, wherein the fungicide is selected from the group consisting of fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, strobilin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, QiI fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

48. The additional agriculturally active compound is 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, ipconazole, myclobutanil, promethazine 48. The composition of any one of claims 45 to 47, 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, flutianil, or a combination thereof.

49. 49. A method of using a composition according to any one of claims 40 to 48, comprising applying the composition to a plant, a part of a plant, the soil in which a plant is growing or to be grown, or the soil in which a seed has been or will be sown.

50. 46. ​​A method of controlling or preventing fungal growth, comprising applying a composition according to any one of claims 40 to 45 to an area having fungal growth or at risk of developing fungal growth.

51. 1. A method for controlling or preventing fungal growth, comprising: combining the composition of any one of claims 39-40 or 42-45 with water to form a particulate suspension comprising particles of the first agriculturally active compound; applying the particulate suspension to an area having fungal growth or at risk of developing fungal growth.

52. 52. The method of claim 51, wherein the method further comprises combining the water-dispersible granules with the additional agriculturally active compound to form the composition.

53. 53. The method of claim 52, wherein combining the water-dispersible granules with the agriculturally active compound comprises adding an amount of the agriculturally active compound to the water-dispersible granules that is less than the amount of the agriculturally active compound recommended for use in the absence of the water-dispersible granules.

54. A method for preparing a dispersion comprising water-dispersible granules according to any one of claims 1 to 39, comprising the steps of: The method includes combining the water-dispersible granules with water and an additional agriculturally active compound to obtain a mixture, wherein the water-dispersible granules and the additional agriculturally active compound are each present in a concentration sufficient to provide a biological effect when the mixture is applied to a crop or produce.

55. 55. The method of claim 54, wherein the concentration of the water-dispersible granules in the mixture ranges from 0.01% to 10% by weight.

56. 56. The method of claim 54 or 55, wherein the method further comprises adding an adjuvant to the mixture.

57. 57. The method of any one of claims 54 to 56, wherein the additional agriculturally active compound is selected from an acaricide, a fungicide, a herbicide, an insecticide, a molluscicide, a nematicide, or a combination thereof.

58. The additional agriculturally active compound is selected from the group consisting of 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 oxysterol binding protein inhibitor (OSBPI) fungicide, a triazole carboxamide fungicide, a carbamate fungicide, a Group 27 fungicide, a benzamide fungicide, a demethylation-inhibiting piperazine fungicide, a demethylation-inhibiting pyrimidine fungicide, and a demethylation-inhibiting 57. The method of any one of claims 54 to 56, wherein the fungicide is selected from an azole fungicide, a morpholine fungicide, a Group U6 fungicide, a Group 50 fungicide, a strobilin fungicide, a quinoline fungicide, an inorganic fungicide, a copper ammonium complex 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 QiI fungicide, a guanidine fungicide, a polyoxin fungicide, a Group 29 fungicide, a thiazolidine fungicide, or a combination thereof.

59. The additional agriculturally active compound is 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, ipconazole, micropig 59. The method of any one of claims 54 to 58, wherein the active ingredient is selected from the group consisting of benzophenone, propiconazole, 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, flutianil, or a combination thereof.

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