Water dispersible granule acylhydrazone adenosine triphosphate diphosphatase inhibitor preparation

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 inhibitor. # imgabs0 #

Description

[0001] Cross - reference to related applications

[0002] This application claims the benefit of the earlier filing date of U.S. Provisional Patent Application No. 63 / 419,635, filed on October 26, 2022, the entire disclosure of which is incorporated herein by reference. Technical field

[0003] The present disclosure relates to water - dispersible granules containing adenosine triphosphatase inhibitors and methods of using the same, particularly methods of use in treating crops susceptible to pathogens. Background art

[0004] Crops around the world are infected by various pathogens. Pathogens such as insects, mites, nematodes, weeds, and fungi have developed a series of mechanisms to survive under pesticides, such as by sequestering, exporting, or detoxifying pesticides. There is a need for formulations that enhance the efficacy of pesticides by blocking certain resistance mechanisms. Summary of the invention

[0005] Disclosed herein is a water - dispersible granule comprising: particles of a first agro - active compound having a structure

[0006]

[0007] a dispersant; and

[0008] optionally a dust inhibitor; 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.

[0009] In one embodiment, the water - dispersible granule comprises particles of a first agro - active compound present in an amount in the range of 5 wt% to 90 wt%, 0.5 wt% to 15 wt%, 30 wt% to 85 wt%, 30 wt% to 40 wt%, or 70 wt% to 85 wt%.

[0010] In one embodiment of the disclosed water - dispersible granule, the dispersant is present in an amount in the range of 1 wt% to 30 wt%, such as about 2 wt% to about 15 wt% or about 3 wt% to about 20 wt%, particularly about 1 wt%, about 3 wt%, about 5 wt%, about 10 wt%, or about 20 wt%.

[0011] In certain embodiments, the dispersant is a high - molecular - weight dispersant.

[0012] 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, such as a molecular weight in the range of 1,000 Daltons to 100,000 Daltons. Dispersants suitable for the water-dispersible granules of the present invention 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 a specific example, the dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyethylene sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinic acid, vinylpyrrolidone / vinylcaprolactam, polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohol, polyethoxylated diamine, naphthalene sulfonate formaldehyde condensate, lignin sulfonate, ethoxylated lignin sulfonate, or combinations thereof.

[0013] In one embodiment of the disclosed water-dispersible granules, a dust inhibitor is included. In one such embodiment, the dust inhibitor is a liquid or a low-melting solid. In certain embodiments, the dust inhibitor is selected from surfactants, waxes, natural oils, chemically modified natural oils, low-volatility organic solvents, or combinations thereof.

[0014] In additional embodiments, the water-dispersible granules disclosed herein may further include a binder. For example, in some embodiments, the binder is present in an amount in the range of 5 wt% to 30 wt%, such as 10 wt% to 25 wt%. In one embodiment, the water-dispersible granules include a binder selected from compounds having a melting point above 100 °C and completely soluble in water during the granulation process.

[0015] 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 carrier or diluent is included in an amount sufficient to balance the weight of the water-dispersible granules to a total of 100 wt%. In specific embodiments, the inert carrier or diluent is selected from starches, wood flours, celluloses, chemically modified celluloses, or mineral materials. Suitable mineral materials include clay alone, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, or combinations with other mineral materials, other carriers or diluents, or both.

[0016] 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 in the range of 0.01 wt% to 1 wt%.

[0017] In one embodiment of the water-dispersible granule, the granules of the first agroactive compound are ground before granulation such that the granules have a volume-weighted median particle size in the range of greater than 0.01 micrometer to 10 micrometers. In one embodiment, after diluting and dispersing the granules in water, the particle size is measured by light scattering, and the particle size range is greater than 0.01 micrometer to 10 micrometers, such as greater than 0.01 micrometer to 5 micrometers, or greater than 0.01 micrometer to 2 micrometers. In one embodiment, the particle size is about 1 micrometer or less such as less than about 1 micrometer, 0.01 micrometer to about 15 micrometers such as about 1 micrometer to about 15 micrometers or about 1 micrometer to about 7 micrometers.

[0018] In one embodiment of the water-dispersible granule disclosed herein, the granule comprises

[0019] (a) granules of a first agroactive compound having the structure

[0020] which are present in an amount in the range of 5 wt% to 85 wt%; and

[0021] (b) 0.5 wt% to 15 wt% of a dust inhibitor selected from surfactants, waxes, natural oils, chemically modified natural oils, low volatility organic solvents or combinations thereof. In another embodiment of such water-dispersible granule, the granule comprises 3 wt% to 20 wt% of a high molecular weight dispersant. In embodiments of such water-dispersible granules, the granules of the first agroactive compound have a volume-weighted median particle size of less than 20 micrometers such as about 15 micrometers or less, about 10 micrometers or less, about 7 micrometers or less such as less than about 2 micrometers, such as those having a volume-weighted median particle size of about 1 micrometer.

[0022] In some embodiments, the water-dispersible granules disclosed herein further comprise an additional agroactive compound. Examples of the additional agroactive compound may be selected from fungicides, insecticides, herbicides, insecticides, molluscicides, nematicides. And in certain embodiments, more than one additional agroactive compound is included in the disclosed water-dispersible granule such that a combination of additional agroactive compounds is also included.

[0023] For example, in certain embodiments, additional agricultural active compounds included in the water-dispersible granules disclosed herein are fungicides, such as fungicides selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0024] More particularly, when the additional agricultural active compound included in the water-dispersible granules of the present invention is a fungicide, particularly useful fungicides include fungicides selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluzasulfuron, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, fluopyram, metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, chlorothalonil, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, cyflufenamid, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, fenarimol, spiroxamine, cyflufenamid, metrafenone, pyrimethanil, pyraclostrobin, azoxystrobin, trifloxystrobin, picoxystrobin, pyraoxystrobin, kresoxim-methyl, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dichloran (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, flutianil or combinations thereof.

[0025] 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 an additional agricultural active compound such that the total amount of the additional agricultural active compound in the composition applied to the crop or agricultural product is lower than the amount typically required and / or recommended to provide the same biological effect in a composition that does not contain the water-dispersible granules.

[0026] Additional agricultural active compounds that can be particularly used in the compositions and methods disclosed herein are fungicides, such as fungicides selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, U6 Group fungicides, Group 50 fungicides, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0027] The disclosed compositions are generally applied to plants, parts of plants, seeds, the soil in which the plants are growing or will grow, or the soil in which seeds have been or will be sown. In one embodiment, the application site is selected to be at risk of fungal growth or where fungal growth has occurred.

[0028] In one embodiment, the water-dispersible granules disclosed herein comprise particles of a first active compound which, after dilution and dispersion of the WDG in water, have a volume-weighted median particle size in the range greater than 0.01 to 20 microns as measured by light scattering. The water-dispersible granules may also comprise an inert carrier and / or diluent. Also disclosed are agricultural compositions comprising the water-dispersible granules and methods of using the same. These compositions may also comprise agricultural active compounds such as acaricides, antimicrobials, fungicides, herbicides, insecticides, molluscicides or nematicides or combinations thereof; and defoamers.

[0029] The foregoing and other objects, features and advantages of the present disclosure will become more apparent from the following detailed description with reference to the accompanying drawings. Detailed Description

[0030] I. Glossary Overview

[0031] The following explanations of terms and methods are provided to better describe the present disclosure and guide those of ordinary skill in the art in practicing the present disclosure. Unless the context clearly indicates otherwise, the singular forms "a", "an", and "the" refer to one or more than one. Unless the context clearly indicates otherwise, the term "or" refers to a single one of the alternative elements or a combination of two or more elements. As used herein, "comprising" means "including". Thus, "comprising A or B" means "including A, B, or A and B", without excluding additional elements. Unless otherwise noted, all references (including patents and patent applications) cited herein are incorporated by reference in their entirety.

[0032] Unless otherwise noted, all numerical values expressing quantities of ingredients, molecular weights, percentages, temperatures, times, etc., used in the specification or claims shall be understood to be modified by the term "about". Thus, unless otherwise implicitly or explicitly stated, the numerical parameters shown are approximations, which may depend on the desired characteristics sought and / or the detection limits under standard test conditions / methods. When distinguishing an embodiment directly and explicitly from the prior art being discussed, the numerical values of the embodiment are not approximations unless the word "about" is explicitly recited.

[0033] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. Although methods and materials similar or equivalent to those described herein can also be used in the practice or testing of the present disclosure, suitable methods and materials are described below. The materials, methods, and examples are illustrative only and not intended to be limiting.

[0034] "Application" refers to any suitable mode of application for controlling pathogens such as fungal pathogens, including treating existing crops, seeds, soil, or combinations thereof.

[0035] "In combination with" refers to applying the compounds simultaneously in a single application or sequentially in two or more different applications that may be separated in time, location, or method.

[0036] "Control" of 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 means reducing one or more pathogens such as fungi to undetectable levels, or reducing or inhibiting a fungal pathogen to an acceptable level determined by one of ordinary skill in the art (e.g., a crop grower). The determination of an acceptable level of pathogen reduction is based on a number of factors, including the crop, the pathogen, the severity of the pathogen, use restrictions, economic thresholds, and other factors known to one of ordinary skill in the art.

[0037] As used herein, the term "enhancer" refers to one or more compounds that enhance the effectiveness of an insecticide as disclosed herein. Without being bound by theory, the enhancer compounds disclosed herein may act by blocking one or more pathways of a pathogen such as a fungal pathogen, such as by detoxifying, sequestering, or transporting the insecticide away from toxicity. In certain embodiments, the enhancer compounds disclosed herein inhibit enzymatic adenosine triphosphate diphosphatase activity, which results in the action of an insecticide (such as an acaricide, an antimicrobial, a fungicide, a herbicide, an insecticide, a molluscicide, and / or a nematicide) being enhanced, potentiated, or synergized. For example, when an enhancer compound is used in combination with a fungicide, the combination of the enhancer and the fungicide enhances the fungicidal effect of the fungicide and / or renders a fungus resistant to the fungicide sensitive due to the activity of the enhancer. Most commonly, these enhancers do not themselves inhibit a pathogen such as a fungus, nor do they have a harmful effect on a living organism that is (or may be) infected by the pathogen.

[0038] As used herein, the term "treatment" refers to a method for applying or applying an effective amount of the disclosed compound or its formulation to a target area of a field and / or a plant. Treatment methods may include, but are not limited to, aerosol spraying, pressure spraying, atomization, chemigation, direct watering, and dipping. Target areas of a plant may include, but are not limited to, the leaves, roots, stems, buds, flowers, fruits, seeds, and bulbs of the plant, including bulbs, corms, rhizomes, tubers, taproots, and rootstocks. Treatment may include methods in which one area of a plant (e.g., the root zone or the foliage) is treated and another area of the plant is protected (e.g., treating the foliage when the disclosed compound is applied to the root zone, or treating new growth when the disclosed compound is applied to the foliage).

[0039] As used herein, the term "water dispersible granule" or "WDG" refers to a dry solid preparation in the form of granules and containing a synergist compound as disclosed herein. WDG typically has a larger average particle size than the particles of wettable powders, thus reducing dust emissions and being flowable. When WDG is added to water, the WDG disperses and / or dissolves to provide a fine particle suspension of the enhancer compound. WDG can be stored as a formulation and can be provided to the market and / or end user without further processing. In actual applications, WDG is prepared for application by the end user. Typically, WDG is mixed with water in the end user's spray tank to provide a fine particle suspension at a concentration suitable for a particular application. The concentration may vary depending on factors such as the crop, pathogen, particular time of year, geographical location, local regulations, and intensity of infection. Once mixed with water at the desired concentration, the resulting fine particle suspension can be applied, such as by spraying.

[0040] II. Formulations

[0041] A common goal of formulators of agricultural products is to maximize the biological activity of the active ingredient. In wettable powders and WDG (typical types of solid preparations), this is particularly challenging because the active ingredient in the solid state tends to limit bioavailability and / or such powders have inhalation hazards and / or are not easily applied. Without being limited by theoretical understanding, it is currently believed that factors that can determine biological activity include solubility in water (including how it varies with temperature, salinity, and pH at the site of application), solubility in hydrophobic regions (including within the waxy leaf cuticle and any micellar surfactant domains), lattice energy, density of the active ingredient crystals and thus their sedimentation tendency, presence of crystal polymorphs and metastable states, diffusion rate in water, ability of the active ingredient to diffuse through the plant cuticle, location of the site where the active ingredient acts, and concentration of the active ingredient required at that site of action. It is possible for formulators to find a large number of modifications to overcome the limitations of biological activity, and many of these modifications have interdependent effects (meaning that testing each modification individually does not fully inform the results when each of them is varied simultaneously), so it is not feasible to explore the entire experimental space.

[0042] Among the formulations tested during the work described in this disclosure, the inventors have found that aqueous suspensions of (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally have poor biological activity. It has further been found that for water dispersible granules (or "WDG") containing the components described herein, by controlling the particle size of (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide within a particular size range, the biological activity is greatly enhanced.

[0043] A common requirement for formulators of agricultural products is to achieve acceptable stability both in terms of chemical stability (meaning that the active ingredient does not undergo significant chemical degradation) and in terms of physical stability (meaning that in the common product containers stored under the conditions typically encountered in the supply chain, the product remains similar to its state at the time of manufacture and the product is suitable and convenient for use by the end user). Whether a particular active ingredient is prone to chemical degradation is unpredictable because multiple factors can determine its behavior. These factors include the solubility of the active ingredient in any liquid phase present (including the hydrophobic phase of any surfactant micelle structure), the presence of chemicals in those liquid phases that may catalyze degradation, any tendency of the active ingredient to undergo autocatalysis such that the decomposition products accelerate further reactions, the presence of chemical bonds within the active ingredient that are prone to cleavage, and the influence of adjacent groups on its sensitivity. Physical stability also has to be evaluated empirically, but it is known in the art that certain small-scale laboratory tests can generally adequately represent the behavior at larger scales in commercial applications.

[0044] In the formulations tested during the work described in the present disclosure, the inventors found that aqueous suspensions of (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally have unacceptable chemical stability. It was further found that for WDG containing the desired components described below, acceptable chemical stability is obtained by controlling the pH within a specific range and by controlling the concentration of certain components that appear to catalyze degradation. Additionally, it was found that WDG containing the components described herein has sufficient physical stability and remains suitable for use even when subjected to stress testing at elevated temperatures (including the temperatures that commercial products may experience during transportation, storage, and use).

[0045] Disclosed herein are WDG (and their formulations) comprising a first agricultural active compound having the structure

[0046]

[0047] also known as (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0048] In some embodiments, in addition to a dispersant and a dust suppressant, the WDG further comprises a first agricultural active compound. In additional embodiments, the WDG can be formulated to comprise a binder, an inert carrier, an antifoaming agent, a diluent, or a combination thereof.

[0049] In some embodiments, for example, the WDG is formulated by the end user to provide a fine particle suspension when mixed with water. In certain embodiments, the first agricultural active compound and the dispersant are intimately mixed together to provide a matrix for forming the WDG. The first agricultural active compound may be completely or partially covered by the dispersant. A dust inhibitor may also be present in the matrix or it may be present as a coating layer on the WDG.

[0050] A. First agricultural active compound

[0051] The WDG contains the first agricultural active compound (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide in an amount sufficient such that when prepared for use (such as when combined with water), the first agricultural active compound is present in an amount sufficient to enhance the efficacy of one or more agricultural active compounds that can be applied in combination with the first agricultural active compound. In some embodiments, the WDG contains from 1 wt% to 90 wt% or more of the first agricultural active compound, such as from 5 wt% to 90 wt%, or from 5 wt% to 85 wt%, or from 10 wt% to 85 wt%, or from 20 wt% to 85 wt%, or from 30 wt% to 85 wt%. In certain embodiments, the WDG contains from 5 wt% to 90 wt% or more of the first agricultural active compound, such as from 30 wt% to 85 wt%, or from 30 wt% to 40 wt%, or from 70 wt% to 85 wt%.

[0052] In some embodiments, at least a portion of the first agricultural active compound is present as particles in the WDG. After dilution and dispersion of the WDG in water, as measured by light scattering, the particles of the first agricultural active compound present in the WDG may have a volume-weighted median particle size ranging from greater than zero microns to 40 microns, such as from 0.01 microns to 40 microns, or from 0.01 microns to 30 microns, 0.01 microns to 25 microns, 0.01 microns to 20 microns, 0.01 microns to 15 microns, 0.01 microns to 10 microns, 0.01 microns to 5 microns, or from 0.01 microns to 2 microns. In certain embodiments, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles of the first agricultural active compound present in the WDG may have a volume-weighted median particle size ranging from 1 micron to 20 microns, such as from 1 micron to 15 microns, or from 2 microns to 10 microns, or from 4 microns to 8 microns.

[0053] B. Dispersant

[0054] The dispersants used to form the WDG of the present disclosure are generally high molecular weight dispersants. In some embodiments, the dispersant may have a molecular weight of 400 Daltons or greater, such as from 400 Daltons to 2,000,000 Daltons, or from 500 Daltons to 1,000,000 Daltons, or from 750 Daltons to 750,000 Daltons, or from 750 Daltons to 500,000 Daltons, or from 1,000 Daltons to 250,000 Daltons, or from 1,000 Daltons to 100,000 Daltons. In certain embodiments, the dispersant has a molecular weight in the range of 1,000 to 100,000 Daltons.

[0055] In some embodiments, the WDG contains from greater than zero to 40 wt% of the dispersant, such as 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% of the dispersant. In certain embodiments, the dispersant is present in an amount in the range of 1 wt% to 30 wt%, such as from 3 wt% to 20 wt%.

[0056] In any embodiment, the dispersant can be selected from anionic dispersants, cationic dispersants, nonionic dispersants, or combinations thereof. In some embodiments, the dispersant is or comprises an anionic dispersant. In other embodiments, the dispersant is or comprises a nonionic 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 combinations thereof. In additional embodiments, the dispersant can be a low metal content dispersant, such as a low sodium non-metal dispersant, a low calcium non-metal dispersant, a low potassium non-metal dispersant, or combinations thereof.

[0057] In any embodiment, the dispersant can be selected from one or more of the following:

[0058] · Homopolymer dispersants, such as but not limited to polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyethylene sulfonate, polyethyleneimine, or combinations thereof;

[0059] · Random or statistical copolymers, such as but not limited to polyethylene glycol / polyisobutylene succinic acid, vinylpyrrolidone / vinylcaprolactam, or combinations thereof;

[0060] · Block copolymers, such as but not limited to polyethylene oxide / polypropylene oxide, fatty acid / polyethylene oxide, polyethoxylated alcohol, polyethoxylated diamine, or combinations thereof;

[0061] · Naphthalene sulfonate formaldehyde condensates;

[0062] · Lignin sulfonates;

[0063] · Ethoxylated lignosulfonate;

[0064] · Or any combination of the above components.

[0065] C. Dust inhibitor

[0066] An optional component of the WDG disclosed in the present invention is a dust inhibitor. The dust inhibitors used in WDG are generally in the form of liquids or low-melting solids. In some embodiments, the low-melting solid is a compound that exists as a solid at ambient temperature but exists as a liquid at a temperature above ambient temperature, such as at a temperature above 30 °C, or above 35 °C, or above 40 °C. In certain embodiments, the dust inhibitor can be selected from surfactants, waxes, natural oils, chemically modified natural oils, or low-volatility organic solvents.

[0067] The dust inhibitor surfactant that can be used in the WDG of the present invention can be a low-molecular-weight surfactant, such as a surfactant with a molecular weight range of 150 daltons to less than 1,200 daltons.

[0068] The dust inhibitor surfactant can be an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium salt surfactant, an amphoteric ion surfactant, or a combination thereof. In some embodiments, the surfactant is an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof.

[0069] In any embodiment, the anionic surfactant is citrate, carbonate, phosphate, phosphonate, sulfate, or sulfonate. The anionic surfactant can be an ester of an alcohol, an alcohol alkoxylate (e.g., alcohol ethoxylate and / or alcohol propoxylate), a triphenylvinylphenol ethoxylate, a fatty acid, a natural oil, or a combination thereof. In certain embodiments, the anionic surfactant is a citrate ester, carbonate ester, phosphate ester, phosphonate ester, sulfate ester, or sulfonate ester of an alcohol, an alcohol alkoxylate, a triphenylvinylphenol ethoxylate, a fatty acid, a natural oil, or any combination thereof. In a specific embodiment, the dust inhibitor surfactant includes lignosulfonate, such as a dust inhibitor surfactant including a mixture of lignosulfate and urea.

[0070] The cationic surfactants suitable for use as dust inhibitors can include ethoxylated amines, such as ethoxylated amines of natural oils, alcohols, fatty acids, or combinations thereof.

[0071] Suitable nonionic surfactants can include alkoxylates of alcohols, natural oils, synthetic oils, or combinations thereof, such as ethoxylates and / or propoxylates of alcohols, oils, or combinations thereof.

[0072] Suitable quaternary ammonium salt surfactants can include at least one chain having at least 6 carbon atoms, such as 6 to 20 carbon atoms or 6 to 12 carbon atoms, attached to the quaternary ammonium head group.

[0073] And in some embodiments, the zwitterionic surfactants used herein as dust inhibitors contain a positively charged group such as a quaternary ammonium ion group, and a negatively charged group such as a carboxylic acid moiety, a sulfonic acid moiety, or a phosphoric acid moiety. An example of a zwitterionic surfactant is cocoamidopropyl betaine.

[0074] In certain embodiments, the surfactant is an anionic surfactant and can be selected from phosphates, phosphonates, sulfates or sulfonates of alcohols, alcohol ethoxylates, triphenylvinylphenol ethoxylates, fatty acids or natural oils, or any combination thereof.

[0075] In other embodiments, the surfactant is a nonionic surfactant and can be selected from alkoxylates of alcohols, natural oils, or combinations thereof.

[0076] Particularly with respect to surfactants, those of ordinary skill in the art will understand that alkoxylate groups (e.g., ethoxylates or propoxylates) can contain one or more alkoxy moieties (i.e., can be polyalkoxylated), such as 1 to 200 or more alkoxy moieties. And in some embodiments, the alkoxylate group includes more than 1 to 200 alkoxy groups, such as 4 to 200 or 4 to 150 alkoxy groups.

[0077] Additional dust inhibitors that can be used in the WDG disclosed herein include waxes such as, but not limited to, petroleum waxes, natural waxes, or plant-based waxes, natural oils such as, but not limited to, vegetable oils or animal-based oils. In certain embodiments, the natural oil used as a dust inhibitor is soybean oil, corn oil, olive oil, cottonseed oil, rapeseed oil, linseed oil, or any other seed or nut oil, castor oil, pine oil, tallow, or any combination thereof. Additional oils used as dust inhibitors in the WDG disclosed herein include chemically modified oils such as, but not limited to, methylated soybean oil, methyl oleate, or any combination thereof.

[0078] Low volatility organic solvents can also be used as dust inhibitors herein. Examples of such low volatility organic solvents include, but are not limited to, paraffin wax or other mineral oils, triethylhexyl phosphate, methyl benzoate, ethyl benzoate, propyl benzoate, or butyl benzoate, or any other known plasticizer, or any combination thereof.

[0079] Without being bound by theory, it is to be understood that the mechanism of action of the dust inhibitor is that when in liquid form, the dust inhibitor physically absorbs any fine particles and weakly binds them to the larger granule particles. Although the fine particles are thus strictly speaking not part of the granule and can be physically removed using special equipment such as a jet air sieve, they are substantially prevented from forming airborne dust. Airborne dust can be monitored by one of several ways known to those skilled in the art, such as by a jet air sieve, or by observing or collecting the amount of material suspended in the air when a sample of the WDG is allowed to fall into a container or an air column.

[0080] The dust inhibitor can be present in the WDG in an amount ranging from greater than zero to 25 wt%, such as 0.1 wt% to 20 wt%, or 0.5 wt% to 20%, or 0.5 wt% to 15 wt%. In certain embodiments, the dust inhibitor is present in an amount ranging from 0.5 wt% to 15 wt% or from about 0.1 wt% to about 2 wt%.

[0081] D. Optional Additives

[0082] In some embodiments, the WDG itself or the WDG formulation may also contain one or more additional components, such as binders, antifoaming agents, inert carriers, diluents, or combinations thereof.

[0083] Suitable binders can include, but are not limited to, compounds that are normally solids at room temperature and have a melting point greater than 100 °C. The binder also typically completely dissolves in water during the granulation process. In some embodiments, the dispersant as described herein can also be used as a binder. In some such embodiments, two (or more) dispersant compounds can be used, or a single dispersant can be used. In additional embodiments, a binder that is not a dispersant can be used. In such embodiments, sugars (e.g., ribose, xylose, glucose, fructose, mannose, sucrose, maltose, isomaltose, trehalose, xylitol, mannitol, sorbitol, dextrose, galactose, lactose, maltodextrin, sucrose, or combinations thereof), cellulose derivatives, synthetic and natural gums, synthetic polymers, etc. can be used as binders. In some embodiments, the binder can be selected from polyvinyl acetate, methylcellulose, hydroxymethylcellulose, or other modified forms of cellulose, animal protein glue, guar gum or modified guar gum, or combinations thereof. In certain embodiments, such binders can be used in an amount ranging from 5 wt% to 30 wt%, such as 5 wt% to 25 wt% or 10 wt% to 25 wt%.

[0084] Suitable inert carriers and diluents can include, but are not limited to, compounds that are typically present as solid materials (such as fine powders) and have a melting point greater than 100 °C. In some embodiments, the inert carriers and diluents are not significantly soluble in water and do not affect biological activity. Exemplary inert carriers and diluents can be selected from starches, wood flours, celluloses, chemically modified celluloses, minerals (such as clays, micas, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, etc.) and combinations thereof. The inert carrier and / or diluent can be used in an amount sufficient to balance the weight of the water-dispersible granule to a total of 100 wt%.

[0085] In some embodiments, the formulation contains one or more defoamers. The defoamer can be selected to reduce or prevent foaming during the manufacture, handling, and / or use of the formulation. In some embodiments, the defoamer is an emulsion of silicone oil. In some embodiments, the defoamer is present in an amount ranging from 0.01 wt% to 1.0 wt%.

[0086] E. Additional agricultural active compounds and compositions

[0087] The WDG formulation can also contain additional agricultural active compounds (i.e., in addition to (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide contained in the WDG). In addition to or alternatively, the WDG can be used in combination with one or more agricultural active compounds, typically as part of an agricultural composition for application to crops, seeds that can be sown to produce crops, harvested agricultural products, and / or soil on which crops have been or may be planted or sown. The agricultural composition can be a fine particle suspension composition that is formed at least in part by combining the disclosed WDG (or its formulation) with a suitable solvent or solvent mixture (such as, but not limited to, water).

[0088] Embodiments of the disclosed WDG can be used to enhance the effects of a variety of agricultural active compounds, including fungicides, antivirals, bactericides, herbicides, insect / acaricides, molluscicides, nematicides, insecticides, plant protectants, synergists, fertilizers, and soil conditioners.

[0089] In one embodiment, the WDG disclosed in the present invention can be used to enhance the fungicidal effects of a variety of fungicides. The fungicides used in combination with the disclosed WDG can include, but are not limited to, the fungicides listed by category in Table 1.

[0090]

[0091]

[0092]

[0093]

[0094] Fungicides are more generally catalogued by the Fungicide Resistance Action Committee (FRAC) in the FRAC Coding List 2022 and reproduced in Appendix 1, the full text of which is incorporated herein by reference.

[0095] In one embodiment, the disclosed WDG is used in combination with one or more compounds from the classes or groups listed in Table 1, 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.

[0096] In certain embodiments, the disclosed WDG is used in combination with one or more fungicides selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0097] Certain fungicides enhanced by use in combination with the disclosed WDG according to the methods herein may include benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluxametamide, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, fluxapyroxad, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, amisulbrom, zineb, chlorobenzyl alcohol, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, fludioxonil, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, penconazole, diclobutrazol, spiroxamine, cyflufenamid, metrafenone, picoxystrobin, oxathiapiprolin, amisulbrom, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, chloranil (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or combinations thereof.

[0098] In some embodiments, treatment with a combination of a selected fungicide and the disclosed WDG provides synergistic fungicidal activity against phytopathogenic fungi.

[0099] In some embodiments, the present disclosure provides compositions and methods for treating plants or plant seeds infected with or at risk of being infected with fungal pathogens. In some such embodiments, the compositions of the present disclosure comprise formulations of a fungicide, the disclosed WDG, and a botanically acceptable carrier. In another embodiment, the fungicide and the WDG are applied in separate compositions. In additional embodiments, an agricultural or horticultural fungicide is used in combination with other compounds in addition to the disclosed WDG. Such other compounds may be applied in the same or separate compositions as the fungicide and / or the WDG. Examples of other components include known carriers for formulation. Additional examples thereof include herbicides, insecticides / acaricides, nematocides, soil insecticides, plant protectants, synergists, fertilizers, soil conditioners, and animal feeds known in the art. In one embodiment, the inclusion of such other components has a synergistic effect on crop growth.

[0100] In certain embodiments, the disclosed WDG is used to enhance the action 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 described in Appendix 2. By way of example, suitable herbicides for use in combination with the disclosed WDG include, but are not limited to, acetyl-CoA synthase inhibitors, acetolactate synthase inhibitors, microtubule assembly inhibitors, microtubule organizing inhibitors, auxin mimics, photosynthesis inhibitors, deoxy-D-xylulose phosphate synthase inhibitors, enolpyruvylshikimate phosphate synthase inhibitors, phytoene desaturase inhibitors, glutamine synthetase inhibitors, dihydropteroate synthase inhibitors, protoporphyrinogen oxidase inhibitors, cellulose synthesis inhibitors, uncouplers, hydroxyphenylpyruvate dioxygenase inhibitors, fatty acid thioesterase inhibitors, serine-threonine protein phosphatase inhibitors, solanesyl diphosphate synthase inhibitors, very long chain fatty acid synthesis inhibitors, homogentisate solanesyltransferase inhibitors, lycopene cyclase inhibitors, and combinations thereof.

[0101] In some embodiments, the disclosed WDG is used to enhance the action of insecticides. Exemplary insecticides for use in combination with the disclosed WDG are known in the art and include, but are not limited to, those described in Appendix 3.

[0102] III. Methods

[0103] Embodiments of the method of using the disclosed WDG include combining the WDG (or its formulation and / or agricultural composition) with a solvent such as water to form an agricultural composition suitable for application to a plant, a part of a plant, a seed, the soil in which the plant is growing or will grow, or the soil in which the seed has been or will be sown. The method may also include applying the agricultural composition to a plant, a part of a plant, a seed, the soil in which the plant is growing or will grow, or the soil in which the seed has been or will be sown.

[0104] In some embodiments, the disclosed agricultural composition comprises one or more agricultural 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 application. Optionally, one or more additional agricultural active compounds may be added before, during, and / or after adding water to the agricultural composition. In some embodiments, the WDG may be formulated to comprise an agricultural active compound.

[0105] In certain embodiments, the WDG does not contain an agricultural active compound, and the agricultural composition is formed by combining the WDG with a suitable solvent such as water to provide a concentration suitable for agricultural use. In such embodiments, forming the agricultural composition may also include adding one or more agricultural active compounds to the water, then adding the WDG while combining the WDG with the water, and / or subsequently adding one or more agricultural active compounds to the aqueous mixture containing the WDG.

[0106] In certain non-limiting embodiments, the disclosed WDG is combined with water to provide a composition suitable for agricultural application, in an amount sufficient to provide from 0.01% to 80% weight / weight in the final composition, or from 25% to 55% in the final composition, such as from 30% to 50%, from 35% to 45%, such as 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% weight / weight of a first active compound. In one embodiment, the first active compound is provided in an amount ranging from 0.01% to 50%, such as from 15% to 50%, from 20% to 45%, from 25% to 40%, such as 0.01, 0.05, 0.1, 0.5, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.5, 3.0, 4.0, 5.0, 7.5, 10, 15, 20, 30, 40 or 50% volume / volume in the final composition comprising the WDG and water.

[0107] In some embodiments, the agricultural active compound is present in the agricultural composition at a concentration less than the concentration of the agricultural active compound recommended in the absence of the WDG disclosed herein, such as in the absence of (E)-3-methyl-N ′ -(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0108] In some embodiments, a method of preparing an agricultural composition includes adding the WDG disclosed herein to water in an amount sufficient to enhance the agricultural active compound, and adding an agricultural active compound in an amount sufficient to provide a concentration in the agricultural composition that is less than the concentration recommended in the absence of the disclosed WDG, such as 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 agricultural active compound can be added to the water in any order, sequentially or substantially simultaneously, to form the agricultural composition.

[0109] In any embodiment, the one or more agroactive compounds can be fungicides, insecticides, herbicides, insecticides, molluscicides, nematicides, or combinations thereof as disclosed herein.

[0110] Embodiments of a method for controlling or preventing fungal growth are also disclosed herein. The method can include applying the agricultural composition described herein to a plant, a part of the plant, a seed, the soil in which the plant is growing or will grow, or the soil in which the seed has been or will be sown.

[0111] As is known to those of ordinary skill in the agricultural art, treatable crops include crops infected by various pathogens, including but not limited to bacteria, viruses, fungal pathogens, mites, nematodes, molluscs, weeds, or other pests. By way of example, such agricultural and horticultural crops that can be treated according to the present disclosure include plants, whether genetically modified or not, including their harvested products, such as: grains; vegetables; root crops; potatoes; trees such as fruit trees, e.g., banana trees, tea trees, coffee trees, or cocoa trees; grasses; turfgrasses; or cotton.

[0112] The agricultural composition containing the disclosed WDG can be applied to every part of the plant, such as leaves, stems, patterns, flowers, flower buds, fruits, seeds, seedlings, roots, tubers, taproots, buds, or cuttings. The WDG (including its formulations and / or agricultural compositions) can also be applied to improved varieties / varieties, cultivars, and mutants, hybrids, and genetically modified embodiments of these plants.

[0113] The agricultural composition containing the disclosed WDG can be used for seed treatment, foliar application, soil application, or water application in order to control various diseases occurring in agricultural or horticultural crops (including flowers, turf, and forage).

[0114] The agricultural composition containing the disclosed WDG can be used to enhance the action of antimicrobials. For example, the disclosed WDG can be used in combination with antimicrobials to combat bacterial and viral infections.

[0115] Embodiments of the disclosed WDG can be used to enhance the action of herbicides. For example, the disclosed WDG can be used in combination with one or more herbicides to control weeds or other unwanted vegetation.

[0116] Embodiments of the disclosed WDG can be used to enhance the action of insecticides. For example, the disclosed WDG can be used in combination with one or more insecticides to control insect pests.

[0117] Embodiments of the disclosed WDG can be used to enhance the action of acaricides or miticides. For example, the disclosed WDG can be used in combination with one or more acaricides to control mites.

[0118] Embodiments of the disclosed WDG can be used to enhance the action of molluscicides. For example, the disclosed WDG can be used in combination with one or more molluscicides to prevent slugs or snails from disturbing crops.

[0119] Embodiments of the disclosed WDG can be used to enhance the action of nematicides. For example, the disclosed WDG can be used in combination with one or more nematicides to prevent nematodes from disturbing crops.

[0120] Embodiments of the disclosed WDG are particularly useful for enhancing the action of fungicides against plant fungal pathogens. Examples of pathogens 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.

[0121] Botrytis cinerea is an airborne plant pathogen with a necrotrophic lifestyle that attacks over 200 crop hosts worldwide. It mainly attacks dicotyledonous plant species (including important protein, oil, fiber, and horticultural crops, grapes, and strawberries), and Botrytis also causes secondary soft rot of fruits and vegetables during storage, transportation, and in the market. Many types of fungicides cannot control Botrytis cinerea due to its genetic plasticity.

[0122] The genus Colletotrichum includes ~600 species that attack over 3,200 monocotyledonous and dicotyledonous plant species. Colletotrichum graminicola mainly infects maize (Zea mays) and causes losses of approximately $1 billion per year in the United States alone (Connell et al., 2012).

[0123] Banana wilt disease, caused by the soil-borne fungus Fusarium oxysporum f.sp. cubense, is a major threat to banana production worldwide. Currently, there are no fungicides that can effectively control the disease after the plant is infected (Peng J et al., 2014).

[0124] The known white mold Sclerotinia sclerotiorum attacks more than 400 host species and is considered one of the most prolific plant pathogens. Most of the infected crop species are dicotyledons, as well as some agriculturally important monocotyledons. Some important crops infected by S. sclerotiorum include legumes (soybeans), most vegetables, stone fruits, and tobacco.

[0125] The ascomycete Verticillium dahliae is a soil-borne fungal plant pathogen that causes vascular wilt 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, fibers, fruits, nut trees, forest trees, and ornamental plants.

[0126] The ascomycete fungus Septoria tritici blotch (anamorph: Septoria tritici) is one of the most important foliar diseases of wheat leaves and occurs wherever wheat is grown. Yield losses caused by this disease range from 25% to 50%, and are particularly high in Europe, the Mediterranean region, and East Africa. Infection by Septoria tritici is initiated by airborne ascospores produced on crop residues from the previous season. Primary infection usually occurs after emergence in spring or autumn. The characteristic of the mature disease is the appearance of necrotic spots on the leaves and stems of infected plants.

[0127] The basidiomycete fungus Sphacelotheca reiliana systemically infects maize (Zea mays) and causes head smut. The yield losses caused by this disease are variable and directly depend on the incidence of the disease. The fungus overwinters in crop debris or soil in the form of diploid teliospores. The flower structure transforms into a sorus containing a large amount of powdery teliospores, similar to the mature gall of common smut.

[0128] Examples of crops treated with the compounds and compositions disclosed by the present invention and plant diseases (pathogens) controlled include, but are not limited to:

[0129] Beet: Cercospora leaf spot (Cercospora beticola), black root rot (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc.

[0130] Peanuts: Brown spot (Mycosphaerella arachidis), leaf mold (Ascochyta sp.), rust (Puccinia arachidis), damping-off (Pythium debaryanum), rust spot (Alternaria alternata), stem rot (Sclerotium rolfsii), black rust (Mycosphaerella berkeleyi), etc.

[0131] Cucumbers: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), gummy stem blight (Mycosp haerella melonis), fusarium wilt (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Coryn espora cassiicola), damping-off (Pythium debaryanum, Rhizoctonia so lani Kuhn), Phomopsis root rot of cucumber (Phomopsis sp.), bacterial leaf spot (Pseudomonas syringae pv. Lechrymans), etc.

[0132] Tomatoes: 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.

[0133] Eggplant: Botrytis cinerea (Botrytis cinerea), black rot (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), leaf mold (Mycovellosiella nattrassii), sclerotinia (Sclerotinia sclerotiorum), Verticillium wilt (Verticillium dahliae), brown spot (Phomopsis vexans), etc.

[0134] Strawberry: Botrytis cinerea (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), Phytophthora rot (Phytophthora cactorum), soft rot (Rhizopus stolonifer), fusarium wilt (Fusarium oxysporum), Verticillium wilt (Verticillium dahliae), etc.

[0135] Onion: neck rot (Botrytis allii), Botrytis cinerea (Botrytis cinerea), leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor), Phytophthora porn disease (Phytophthora porn), etc.

[0136] Cabbage: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. campestris, Pseudomonas syringae pv. maculicola, Pseudomonas syringae pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia (Sclerotinia sclerotiorum), black spot (Alternaria brassicicola), Botrytis cinerea (Botrytis cinerea), etc.

[0137] Common bean: Sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular leaf spot (Phaeoisariopsis griseola), etc.

[0138] Apple: Powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), brown rot (Monilinia mali), black spot (Mycosphaerella pomi), canker (Valsa mali), alternaria leaf spot (Alternaria mali), rust (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), leaf rot (Diplocarpon mali), flyspeck (Zygophiala jamaicensis), sooty blotch (Gloeodes pomigena), violet root rot (Helicobasidium mompa), gray mold (Botrytis cinerea), etc.

[0139] Japanese apricot: Scab (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), etc.

[0140] Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), etc.

[0141] Peach: Brown rot (Monilinia fructicola), scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), bacterial leaf spot (Xanthomonas campestris pv. pruni), etc.

[0142] Apricot: Brown rot (Monilinia taxa), Spot disease (Stigminacarpophila), Scab (Cladosporium carpophilum), Red leaf spot (Polystigma rubrum), Target spot (Alternaria alternata), Anthracnose (Colletotrichum gloeospoides), etc.

[0143] Yellow peach: Brown rot (Monilinia fructicola), Anthracnose (Colletotrichum acutatum), Black spot (Alternaria sp.), Sclerotinia of young fruit (Monilinia kusanoi), etc.

[0144] Grape: Gray mold (Botrytis cinerea), Powdery mildew (Uncinula necator), Black rot (Glomerella cingulata, Colletotrichum acutatum), Downy mildew (Plasmopara viticola), Anthracnose (Elsinoe ampelina), Brown spot (Pseudocercospora vitis), Black rot (Guignardia bidwellii), White rot (Coniella castaneicola), Rust (Phakopsora ampelopsidis), etc.

[0145] Pear: Scab (Venturia nashicola), Rust (Gymnosporangium asiaticum), Black spot (Alternaria kikuchiana), Ring rot (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali), Spruce canker (Phomopsis fukushii), Brown spot (Stemphylium vesicarium), Anthracnose (Glomerella cingulata), etc.

[0146] Tea: zonate spot disease (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), etc.

[0147] Citrus fruits: black spot (Elsinoe fawcettii), blue mold (Penicillium italicum), common green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black rot (Diaporthe citri), powdery mildew (Oidium sp.), etc.

[0148] Wheat: powdery mildew (Blumeria graminis f.sp.tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow mold (Pythium iwayamai), pink snow mold (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf scorch (Septoria tritici), glume blotch (Leptosphaeria nodorum), patchy snow blight (Typhula incarnata), sclerotial snow blight (Myriosclerotinia borealis), damping-off (Gaeumannomyces graminis), ergot (Claviceps purpurea), common bunt (Tilletia caries), loose smut (Ustilago nuda), etc.

[0149] Barley: leaf spot (Pyrenophora graminea), net blotch (Pyrenophora teres), leaf spot (Rhynchosporium secalis), loose smut (Ustilago tritici, U. nuda), etc.

[0150] Rice: blast (Pyricularia oryzae), sheath rot (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), brown spot (Cochliobolus miyabeanus), damping-off (Pythium graminicola), bacterial leaf blight (Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantarii), brown stripe (Acidovorax avenae), bacterial grain rot (Burkholderia glumae), Cercospora leaf spot (Cercospora oryzae), false smut (Ustilaginoidea virens), brown leaf spot (Alternaria, Curvularia intermedia), rice grain discoloration (Alternaria padwickii), rice grain powdering (Epicoccum purpurascens), etc.

[0151] Tobacco: sclerotinia (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum), Phytophthora rot (Phytophthora nicotianae), etc.

[0152] Tulip: gray mold (Botrytis cinerea), etc.

[0153] Sunflower: downy mildew (Plasmopara halstedii), sclerotinia (Sclerotinia sclerotiorum), etc.

[0154] Evergreen grass: Sclerotinia blight (Sclerotinia borealis), Rhizoctonia blight (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Rice blast (Pyricularia sp.), Pythium root rot (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc.

[0155] Orchard grass: Powdery mildew (Erysiphe graminis), etc.

[0156] Soybean: Purple blotch (Cercospora kikuchii), Downy mildew (Peronospora manshurica), Phytophthora rot (Phytophthora sojae), Rust (Phakopsora pachyrhizi), Sclerotinia rot (Sclerotinia sclerotiorum), Anthracnose (Colletotrichum truncatum), Gray mold (Botrytis cinerea), Elsinoe leaf spot (Elsinoe glycines), Black stem rot (Diaporthe phaseolorum var. sojae), etc.

[0157] Potato: Phytophthora rot (Phytophthora infestans), Early blight (Alternaria solani), Rhizoctonia peel rot (Thanatephorus cucumeris), Verticillium wilt (Verticillium albo - atrum, Verticillium dahliae, Verticillium nigrescens, etc.).

[0158] Banana: Panama disease (Fusarium oxysporum), Banana leaf spot (Mycosphaerella fijiensis, Mycosphaerella musicola), etc.

[0159] Rapeseed: Sclerotinia rot (Sclerotinia sclerotiorum), Root rot (Phoma lingam), Black leaf spot (Alternaria brassicae), etc.

[0160] Coffee: Rust (Hemileia vastatrix), Anthracnose (Colletotrichum coffeanum), Leaf spot (Cercospora coffeicola), etc.

[0161] Sugarcane: Brown rust (Puccinia melanocephala), etc.

[0162] Maize: Banded leaf spot (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago maydis), brown spot (Cochliobolus heterostrophus), northern leaf blight (Setosphaeria turcica), etc.

[0163] Cotton: Seedling blight (Pythium sp.), rust (Phakopsora gossypii), sour rot (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.

[0164] IV. Process

[0165] The disclosed WDG can be prepared by combining a first agroactive compound according to the present disclosure with a dispersant and optionally a dust inhibitor. In a particular embodiment, the WDG is prepared by combining granules of the first agroactive compound with a dispersant to provide granules formed from a matrix comprising the first agroactive compound and the dispersant. In a particular embodiment, the granules of the first agroactive compound are ground and then blended with other optional components such as a dispersant, and subsequently the resulting mixture is granulated to provide porous granules. In some other embodiments, the granules of the first agroactive compound are ground and granulated to form porous granules while being bound together and coated with a dispersant.

[0166] In some embodiments, the method comprises providing a first agroactive compound, a dispersant, and optionally a dust suppressant and forming a WDG. Optionally, a binder, an inert carrier, a diluent, and / or an additional agroactive compound may also be added. In some embodiments, the first agroactive compound is milled to a desired particle size, such as the particle sizes described herein. A specific particle size or size range of the granule formulation can be achieved by milling in an aqueous suspension prior to granulation or alternatively by a method such as jet milling or other methods known to those skilled in the art of such formulations. The first agroactive compound can then be granulated with the dispersant. In some embodiments, the first agroactive compound is granulated upon addition of the dispersant, followed by addition of the dust suppressant. In other embodiments, the first agroactive compound is combined with the dispersant and the mixture is granulated, followed by combination with the dust suppressant. The optional components can be added at any time during the preparation of the WDG. Any carrier or diluent present can be combined with the first agroactive compound prior to the granulation process, and the method of combination can be any of several methods known to those skilled in the art, such as by ribbon blending or milling the components together. The dispersant and any binder present can be combined with the first agroactive compound prior to the granulation process or can be added during the granulation process. If added prior to granulation, it can be added by any of several methods known to those skilled in the art, such as by adding a solution or powder during or after ribbon blending or kneading. If added during granulation, it is typically added by spraying or pouring a binder solution. Those of ordinary skill in the art will understand that the dispersant and the dust suppressant and any optional components such as inert carriers, diluents, and / or additional agroactive compounds can be added in any suitable or convenient order.

[0167] The granulation process can be carried out by one of several methods known to those skilled in the art, such as by extrusion, fluidized bed granulation, or pan granulation. The details of the component addition sequence can vary as described above and conveniently, but those skilled in the art will understand that fluidized bed granulation is carried out with the addition of water or solvent during the fluidized bed process, followed by evaporation of at least a portion of the water or solvent. 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 during the granulation process, and these granules require a subsequent drying step.

[0168] V. OVERVIEW OF EMBODIMENTS

[0169] Embodiments of water-dispersible granules are disclosed herein that comprise a structure a first agricultural active compound; a dispersant; and optionally a dust inhibitor; 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. This means that the median diameter as measured by light scattering is greater than 0.01 microns to 20 microns.

[0170] In any or all embodiments, the particles of the first agricultural active compound are present in an amount in the range of 5 wt% to 90 wt%.

[0171] In any or all embodiments, the dust inhibitor is present in an amount in the range of 0.5 wt% to 15 wt%.

[0172] In any or all embodiments, the dispersant is present in an amount in the range of 1 wt% to 30 wt%.

[0173] In any or all embodiments, the particles of the first agricultural active compound are present in an amount in the range of 30 wt% to 85 wt%.

[0174] In any or all embodiments, the particles of the first agricultural active compound are present in an amount in the range of 30 wt% to 40 wt%.

[0175] In any or all embodiments, the particles of the first agricultural active compound are present in an amount in the range of 70 wt% to 85 wt%.

[0176] In any or all embodiments, the dust inhibitor is a liquid or a low melting point solid.

[0177] In any or all embodiments, the dust inhibitor is selected from surfactants, waxes, natural oils, chemically modified natural oils, low volatility organic solvents, or combinations thereof.

[0178] In any or all embodiments, the dispersant is a high molecular weight dispersant.

[0179] In any or all embodiments, the dispersant has a molecular weight in the range of 400 daltons to 2,000,000 daltons.

[0180] In any or all embodiments, the dispersant has a molecular weight in the range of 1,000 daltons to 100,000 daltons.

[0181] In any or all embodiments, the dispersant is an anionic dispersant, a cationic dispersant, a nonionic dispersant, or a combination thereof.

[0182] In any or all embodiments, the dispersant is an anionic dispersant.

[0183] In any or all embodiments, the dispersant is a nonionic dispersant.

[0184] In any or all embodiments, the dispersant is selected from homopolymer dispersants, random or statistical copolymers, block copolymers, or combinations thereof.

[0185] In any or all embodiments, the dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyethylene sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinic acid, vinylpyrrolidone / vinylcaprolactam, poly(ethylene oxide) / poly(propylene oxide), fatty acid / polyethylene oxide, polyethoxylated alcohols, polyethoxylated diamines, naphthalene sulfonate formaldehyde condensates, lignosulfonates, ethoxylated lignosulfonates, or combinations thereof.

[0186] In any or all embodiments, the dispersant is present in an amount ranging from 3 wt% to 20 wt%.

[0187] In any or all embodiments, the water-dispersible granule further comprises a binder.

[0188] In any or all embodiments, the binder is present in an amount ranging from 5 wt% to 30 wt%.

[0189] In any or all embodiments, the binder is present in an amount ranging from 10 wt% to 25 wt%.

[0190] In any or all embodiments, the binder is selected from compounds having a melting point higher than 100 °C and that are completely soluble in water during the granulation process.

[0191] In any or all embodiments, the water-dispersible granule further comprises one or more inert carriers, diluents, or combinations thereof.

[0192] In any or all embodiments, the inert carrier or diluent is included in an amount sufficient to balance the weight of the water-dispersible granule to a total of 100 wt%.

[0193] In any or all embodiments, the inert carrier or diluent is selected from starch, wood flour, cellulose, chemically modified cellulose, or mineral materials.

[0194] In any or all embodiments, the mineral materials are selected from clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, or combinations thereof.

[0195] In any or all embodiments, the water-dispersible granule further comprises an antifoaming agent.

[0196] In any or all embodiments, the antifoaming agent is an emulsion of silicone oil.

[0197] In any or all embodiments, the antifoaming agent is present in an amount ranging from 0.01 wt% to 1 wt%.

[0198] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from greater than 0.01 microns to 10 microns.

[0199] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from about 1 micron or less to about 15 microns.

[0200] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from about 1 micron to about 15 microns.

[0201] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from about 1 micron to about 7 microns.

[0202] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from greater than 0.01 microns to 5 microns.

[0203] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size ranging from greater than 0.01 microns to 2 microns.

[0204] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size of about 15 microns or less.

[0205] In any or all embodiments, the particles of the first agricultural active compound are ground before granulation such that after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size of about 7 microns or less.

[0206] In any or all embodiments, the granules of the first agroactive compound are ground prior to granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the granules have a volume-weighted median particle size of about 1 micron.

[0207] In any or all embodiments, the water-dispersible granule comprises:

[0208] (a) granules of a first agroactive compound having the structure which are present in an amount ranging from 5 wt% to 85 wt%;

[0209] (b) 0.5 wt% to 15 wt% of a dust inhibitor selected from surfactants, waxes, natural oils, chemically modified natural oils, low volatility organic solvents or combinations thereof; and

[0210] (c) 3 wt% to 20 wt% of a high molecular weight dispersant;

[0211] wherein the granules of the first agroactive compound have a volume-weighted median particle size of less than 2 microns.

[0212] Embodiments of a composition are also disclosed herein, the composition comprising a water-dispersible granule according to any or all of the above embodiments; and an additional agroactive compound.

[0213] In any or all embodiments, the additional agroactive compound is a fungicide, insecticide, herbicide, insect killer, molluscicide, nematicide or a combination thereof.

[0214] In any or all embodiments, the additional agroactive compound is a fungicide selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide fungicides, phenylamide fungicides, phosphonate fungicides, cinnamic acid fungicides, oxysterol binding protein inhibitor (OSBPI) fungicides, triazolecarboxamide fungicides, carbamate fungicides, Group 27 fungicides, benzamide fungicides, demethylation-inhibiting piperazine fungicides, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, U6 Group fungicides, Group 50 fungicides, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylenebisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0215] In any or all embodiments, the agroactive compound is a fungicide selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluopyram, isofetamid, prothioconazole, oxycarboxin, pythiathion, fluopyram, tridemorph, chlorothalonil, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, cyflufenamid, metconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, bitertanol, fenpropidin, spiroxamine, cyflufenamid, metrafenone, pyrimethanil, azoxystrobin, oxadixyl, imazoxazole, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dichloran (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or combinations thereof.

[0216] In any or all embodiments, the composition further comprises water.

[0217] In any or all embodiments, the water dispersible granule is present in the composition in an amount sufficient to enhance the biological effect of the additional agricultural active compound such that the total amount of the additional agricultural active compound in the composition applied to the crop or agricultural product is lower than the amount typically required and / or recommended to provide the same biological effect in a composition that does not contain the water dispersible granule.

[0218] In any or all embodiments, the additional agricultural active compound is a fungicide, insecticide, herbicide, insecticide, molluscicide, nematicide, or a combination thereof.

[0219] In any or all embodiments, the additional agricultural active compound is a fungicide selected from the group consisting of benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation inhibiting pyrimidine fungicides, demethylation inhibiting azole fungicides, morpholine fungicides, U6 Group fungicides, Group 50 fungicides, methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylenebisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or a combination thereof.

[0220] In any or all embodiments, the additional agroactive compound is a fungicide selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluxametamide, indoxacarb, isofetamid, oxycarboxin, pirifenox, pyraclostrobin, prothioconazole, solatenol, metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, chlorothalonil, quintozene, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram, or a combination thereof.

[0221] Also disclosed herein is a method of using a composition according to any or all of the above embodiments, the method comprising applying the composition to a plant, a part of a plant, a seed, soil in which a plant is growing or is to grow, or soil in which a seed has been or is to be sown.

[0222] Also disclosed herein is an embodiment of a method for controlling or preventing fungal growth, the method comprising applying a composition according to any or all of the above embodiments to a site where fungal growth has occurred or is at risk of occurring.

[0223] Also disclosed herein is an embodiment of a method for controlling or preventing fungal growth, the method comprising combining a composition according to any or all of the above embodiments with water to form a fine particle suspension comprising particles of a first agroactive compound; and applying the fine particle suspension to a site where fungal growth has occurred or is at risk of occurring.

[0224] In any or all embodiments, the method further comprises combining a water-dispersible granule and an additional agroactive compound to form a composition.

[0225] In any or all embodiments, combining the water-dispersible granule and the agroactive compound comprises adding an amount of the agroactive compound to the water-dispersible granule, the amount being less than the amount of the agroactive compound recommended for use in the absence of the water-dispersible granule.

[0226] Embodiments of a method for preparing a dispersion are also disclosed herein, the dispersion comprising a water-dispersible granule according to any or all of the above embodiments, the method comprising: combining the water-dispersible granule with water and an additional agroactive compound to provide a mixture, wherein each of the water-dispersible granule and the additional agroactive compound is included at a concentration sufficient to provide a biological effect when the mixture is applied to a crop or agricultural product.

[0227] In any or all embodiments, the concentration of the water-dispersible granule in the mixture ranges from 0.01 wt% to 10 wt%.

[0228] In any or all embodiments, the method further comprises adding an adjuvant to the mixture.

[0229] In any or all embodiments, the additional agroactive compound is selected from acaricides, fungicides, herbicides, insecticides, molluscicides, nematicides, or combinations thereof.

[0230] In any or all embodiments, the additional agroactive compound is selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0231] In any or all embodiments, the additional agroactive compound is selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluxametamide, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, fluopyram, metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, cyazofamid, thifluzamide, cymoxanil, propamocarb, fluopicolide, zineb, mancozeb, maneb, metiram, ferbam, thiram, ziram, chlorothalonil (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or combinations thereof.

[0232] VI. Examples

[0233] Example 1

[0234] Preparation of a stable and effective granule by extrusion

[0235] An adequate amount of the first active compound is air-milled to obtain at least 100 g of material with a median diameter of less than 1.5 microns, as measured on a Malvern Mastersizer 3000. 40 g of this powder is combined with 25 g of Tamol SN used as a dispersant and binder, 1 g of the dust inhibitor surfactant Surfonic L24-7, 34 g of starch powder as an inert filler, and 0.1 g of the defoamer SAG 1572. The composition is mixed with 50 g of water in a planetary mixer to obtain a viscous paste. The paste is extruded through a screen with a 1 mm opening to produce granules, and these granules are dried overnight in a vacuum oven at 60 °C. Sub-samples are stored at several different temperatures, and the pH, appearance, dispersibility, and suspension stability are evaluated regularly. It is expected that the formulation will have excellent handling properties, excellent physical stability, and biological efficacy comparable to an aqueous suspension of first active compound particles of similar size.

[0236] Example 2

[0237] Preparation of Stable and Effective Granules by Disk Granulation

[0238] 40 g of the first active compound ground as above to obtain a particle size with a median diameter of less than 1.5 µm was combined 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 the dust inhibitor surfactant Surfonic L24-7 in a ribbon blender. The powder was placed in a rotating inclined flat pan, and water was sprayed to form granules, which were dried overnight in a vacuum oven at 60 °C. Sub-samples were stored at several different temperatures, and pH, appearance, dispersibility, and suspension stability were evaluated regularly. The formulation was expected to have excellent physical stability, excellent handling characteristics, and biological efficacy comparable to an aqueous suspension of first active compound particles of similar size.

[0239] Example 3

[0240] Preparation of Stable and Effective Granules by Fluidized Bed Granulation

[0241] 255 g of the first active compound ground as above to obtain a particle size with a median diameter of less than 1.5 µm was placed in the chamber of a fluidized bed granulator and fluidized at an inlet air temperature of 70 °C. 15 g of the dispersant and binder Tamol SN and 15 g of the binder Star-Dri 15 as a 40 wt% total solids aqueous solution were sprayed into the chamber, followed by spraying sufficient water to produce acceptable granules. The air flow was then continued to evaporate the water, after which 15 g of the dust inhibitor surfactant Surfonic L24-7 was sprayed into the chamber. Sub-samples were stored at several different temperatures, and pH, appearance, dispersibility, and suspension stability were evaluated regularly. The formulation was expected to have excellent handling characteristics, excellent physical stability, and biological efficacy comparable to an aqueous suspension of first active compound particles of similar size.

[0242] Example 4

[0243] Efficacy as a Function of Particle Size

[0244] Method: Prepare three different aqueous suspension concentrates with 30 wt% NGXT-1915 containing 2.5 wt% triphenylvinylphenol polyoxyethylene ether surfactant, 2.0 wt% ethylene oxide-propylene oxide block copolymer dispersant, 5.0 wt% propylene glycol antifreeze protectant, 0.1 wt% silicone oil defoamer, and 52.4% distilled water, and grind them. Then add 8.0 wt% viscosity modifier gel, which contains 2.0% xanthan gum and 1.0% biocide aqueous solution. For these three samples, control the grinding conditions to achieve a certain range of particle sizes. Specifically, grind using ceramic grinding media in a water-jacketed stirring vessel, and the duration of grinding is varied. Dilute the samples in water and conduct bioassays in pairs with commercial fungicides Amistar (0.03 L / ha), Imtrex (0.35 L / ha), Proline (0.125 L / ha), or Balaya (0.2 L / ha) at a rate of 20 ppm NGXT-1915 in a greenhouse. Use each paired combination to attack each of four commercially important pathogenic fungi: Botrytis cinerea (on tomato plants), Septoria tritici (on wheat plants), Puccinia triticina (on wheat plants), and Phakopsora pachyrhyzi (on soybean cultivar Siverka). Use Petersfield potting compost (75% medium-grade peat, 12% screened sterilized loam, 3% medium-grade vermiculite, 10% coarse sand (5 mm screened, lime-free), 1.5 kg PG mixture / m ∧3. Lime was added to bring the pH to 5.5 - 6.0 and a wetting agent (Vitax Ultrawet at 200 ml / m³). Seeds were sown in 9 cm diameter pots to a depth of 1 - 2 cm and germinated / grown at 23 °C under a 16 h day / 8 h night light regime. Plants were treated two to three weeks after sowing when they were at the BBCH 11 growth stage (when the first pair of true leaves (single leaves) had unfolded). Using a tracked sprayer, plants were treated with a commercial fungicide and NGXT - 1915 using a water volume of 200 L / ha. Twenty - four hours after treatment, plants were inoculated with the appropriate fungus (pathogen). Each combination of fungicide, pathogen, and formulation was used with four replicates. After disease symptoms had fully developed (depending on the pathogen) between seven and twenty days, the percent disease control of each plant was evaluated. Appropriate controls were used for all experiments, including the inoculated 'checks' where plants were inoculated with the specific pathogen of the plant to assess disease levels. Additionally, each commercial fungicide was tested separately as part of each treatment, which was the 'control' benchmark for evaluating the experimental compounds. The percent disease control of each treated plant was calculated as the average disease severity of the inoculated but untreated plants ('check') minus the average disease severity of the treated plants, divided by the 'check'. The percent synergy of each combination of formulation plus fungicide (test combination) was calculated as the disease control of plants treated with only the fungicide ('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 the fungicide, expressed as a percentage of the maximum possible benefit, so 100% would mean complete disease control and 0% would mean no benefit from the combination.

[0245] Results:

[0246] The particle size of the ground samples was measured using a laser scattering instrument, and the median volume - weighted particle diameters were 1.0, 7.0, and 15 µm respectively as the grinding duration decreased. In the following discussion, for simplicity, these samples are designated as A1, B7, and C15.

[0247] Septoria tritici: There was no consistent synergy with Amistar. The synergy with Imtrex was 28%, 28%, and 4.6% for A1, B7, and C15 respectively. The synergy with Proline was 26%, 25%, and 61% for A1, B7, and C15 respectively. The synergy with Balaya was 51%, 40%, and 36% for A1, B7, and C15 respectively

[0248] Phakopsora pachyrhizi: Synergistic effect with Amistar is 30% for A1 and there is no synergistic effect for B7 or C15, no significant synergistic effect with Imtrex and Proline, and synergistic effect with Balaya is 40%, 33% and 20% for A1, B7 and C15 respectively

[0249] Puccinia triticina: No significant synergistic effect with Amistar, synergistic effect with Imtrex is 29%, 3% and no synergistic effect for A1, B7 and C15 respectively, no significant synergistic effect with Proline or Balaya

[0250] Botrytis cinerea: No significant synergistic effect with Amistar, synergistic effect with Imtrex is 18%, 6% and no synergistic effect for A1, B7 and C15 respectively, synergistic effect with Proline is 33%, 14% and 10% for A1, B7 and C15 respectively, no significant synergistic effect with Balaya.

[0251] Conclusion: The composition of the suspension concentrate sample was chosen to achieve physical properties that are at least suitable for greenhouse assays. These components ensured effective spray deposition and leaf coverage to enable the evaluation of the effect of particle size on biological efficacy. Although the particles were not formulated as water-dispersible granules in this case, it would be routine for a person skilled in the art to make such a formulation without changing the particle size or altering the biological efficacy. Therefore, we conclude that the findings regarding particle size apply to water-dispersible granules. The specific method used to control particle size in this example can be directly used to obtain specific particles for formulating granules by grinding in an aqueous suspension before granulation, or alternative methods such as jet milling can be used without changing the conclusion that particle size has a surprising effect on biological efficacy.

[0252] In the presence of synergistic effects, if we group the results by fungicide, the following results can be highlighted:

[0253] a) In combination with Imtrex, B7 is always superior to C15, and A1 is essentially the same as B7 (1 case) or superior to B7 (3 cases), i.e., A1 > B7 > C15.

[0254] b) In combination with Balaya, B7 > C15.

[0255] c) In combination with Amistar, there is only a synergistic effect and an obvious trend against Phakopsora pachyrhizi, where again A1 > B7 > C15.

[0256] d) In combination with Proline, in one case A1 > B7 > C15, while in another case C15 > A1 = B7.

[0257] However, in the presence of synergy, if we group the results by pathogen, the following results can be highlighted:

[0258] a) Against Septoria tritici, in combination with Imtrex, A1 = B7 > C15; in combination with Proline, C15 > A1 = B7; in combination with Balaya, A1 > B7 > C15.

[0259] b) Against Phakopsora pachyrhizi, in combination with Amistar, only A1 has synergy; in combination with Balaya, A1 > B7 > C15.

[0260] c) Against Puccinia triticina, in combination with Imtrex, A1 > B7 > C15.

[0261] d) Against Botrytis cinerea, for both the combination with Imtrex and the combination with Proline, A1 > B7 > C15

[0262] In this series of experiments, there is an obvious counterexample of Proline against Septoria tritici (a possible outlier based on C15), while the other seven examples establish the pattern. Overall, the suspension concentrate with a median particle size of 1 micron is more biologically effective than the suspension concentrate with a median particle size of 7 microns, and the suspension concentrate with a median particle size of 7 microns is more biologically effective than the suspension concentrate with a median particle size of 15 microns. This pattern is effective against all pathogens tested in this article. Among the fungicides tested in this article, this effect is most consistent with Imtrex and Balaya, but there are also examples of other fungicides.

[0263] We further conclude that in the wettable granule formulation, if the median particle size is approximately 1 micron (measured in this case and after dispersion into water suitable for spray application), the biological efficacy is higher than when the median particle size is approximately 7 microns, and if the median particle size is 7 microns, the biological efficacy is higher than when the median particle size is approximately 15 microns.

[0264] Appendix 1

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] Appendix 2

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] Appendix 3

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313] In view of the many possible embodiments to which the principles of the present disclosure may be applied, it should be recognized that the illustrated embodiments are only preferred examples and should not be regarded as limiting the scope of the present disclosure. On the contrary, the scope of the present disclosure is defined by the following claims. We therefore claim as our invention all that comes within the scope and spirit of these claims.

Claims

1. A water-dispersible granule, said water-dispersible granule comprising: Particles of a first agroactive compound having a structure ; and a dispersant; wherein the granules of the first active compound have a volume-weighted median particle size in the range greater than 0.01 μm to 20 μm.

2. The water-dispersible granule according to claim 1, said water-dispersible granule further comprising a dust inhibitor.

3. The water-dispersible granule according to claim 1, wherein the granules of the first agricultural active compound are present in an amount in the range of 5 wt% to 90 wt%.

4. The water-dispersible granule according to claim 2, wherein the dust inhibitor is present in an amount in the range of 0.5 wt% to 15 wt%.

5. The water-dispersible granule according to any one of claims 1 to 4, wherein the dispersant is present in an amount in the range of 1 wt% to 30 wt%.

6. The water-dispersible granule according to any one of claims 1 to 5, wherein the granules of the first agricultural active compound are present in an amount in the range of 30 wt% to 85 wt%.

7. The water-dispersible granule according to claim 6, wherein the granules of the first agricultural active compound are present in an amount in the range of 30 wt% to 40 wt%.

8. The water-dispersible granule according to claim 6, wherein the granules of the first agricultural active compound are present in an amount in the range of 70 wt% to 85 wt%.

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

10. The water-dispersible granule according to any one of claims 2 to 9, wherein the dust inhibitor is selected from surfactants, waxes, natural oils, chemically modified natural oils, low-volatility organic solvents, or combinations thereof.

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

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

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

14. The water-dispersible granule 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. The water-dispersible granule according to claim 14, wherein the dispersant is an anionic dispersant.

16. The water-dispersible granule according to claim 14, wherein the dispersant is a non-ionic dispersant.

17. The water-dispersible granule according to 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. The water-dispersible granule according to any one of claims 1 to 14, wherein the dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, polyethylene sulfonate, polyethyleneimine, polyethylene glycol / polyisobutylene succinic acid, vinylpyrrolidone / vinylcaprolactam, poly(ethylene oxide) / poly(propylene oxide), fatty acid / poly(ethylene oxide), polyethoxylated alcohol, polyethoxylated diamine, naphthalene sulfonate formaldehyde condensate, lignin sulfonate, ethoxylated lignin sulfonate, or a combination thereof.

19. The water-dispersible granule according to any one of claims 1 to 18, wherein the dispersant is present in an amount ranging from 3 wt% to 20 wt%.

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

21. The water-dispersible granule according to claim 20, wherein the binder is present in an amount ranging from 5 wt% to 30 wt%.

22. The water-dispersible granule according to claim 20 or 21, wherein the binder is present in an amount ranging from 10 wt% to 25 wt%.

23. The water-dispersible granule according to any one of claims 20 to 22, wherein the binder is selected from compounds having a melting point higher than 100 °C and completely soluble in water during the granulation process.

24. The water-dispersible granule according to any one of claims 1 to 23, wherein the water-dispersible granule further comprises one or more inert carriers, diluents, or a combination thereof.

25. The water-dispersible granule according to claim 24, wherein the inert carrier or diluent is included in an amount sufficient to balance the weight of the water-dispersible granule to a total of 100 wt%.

26. The water-dispersible granule 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. The water-dispersible granule according to claim 26, wherein the mineral material is selected from clay, mica, perlite, talc, gypsum, silica, alumina, chalk, diatomaceous earth, or a combination thereof.

28. The water-dispersible granule according to any one of claims 1 to 27, wherein the water-dispersible granule further comprises an antifoaming agent.

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

30. The water-dispersible granule according to claim 28, wherein the antifoaming agent is present in an amount ranging from 0.01 wt% to 1 wt%.

31. The water-dispersible granule according to any one of claims 1 to 27, wherein the granules of the first agricultural active compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the granules have a volume-weighted median particle size ranging from greater than 0.01 micrometer to about 15 micrometers.

32. The water-dispersible granule according to any one of claims 1 to 27, wherein the particles of the first agroactive compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size in the range of greater than 0.01 μm to 10 μm.

33. The water-dispersible granule according to any one of claims 1 to 27, wherein the particles of the first agroactive compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size of less than about 7 μm.

34. The water-dispersible granule according to any one of claims 1 to 27, wherein the particles of the first agroactive compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size in the range of greater than 0.01 μm to 5 μm.

35. The water-dispersible granule according to claim 31, wherein the particles of the first agroactive compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size in the range of greater than 0.01 μm to 2 μm.

36. The water-dispersible granule according to any one of claims 1 to 27, wherein the particles of the first agroactive compound are ground before granulation such that, after dilution and dispersion of the WDG in water, as measured by light scattering, the particles have a volume-weighted median particle size of about 1 μm.

37. A water-dispersible granule, the water-dispersible granule comprising: (a) Particles of a first agroactive compound having a structure which are present in an amount in the range of 5 wt% to 85 wt%; and (b) 3 wt% to 20 wt% of a high molecular weight dispersant; wherein the particles of the first agroactive compound have a volume-weighted median particle size of less than 2 μm.

38. The water-dispersible granule according to claim 37, the water-dispersible granule further comprising 0.5 wt% to 15 wt% of a dust inhibitor selected from surfactants, waxes, natural oils, chemically modified natural oils, low volatility organic solvents, or combinations thereof.

39. The water-dispersible granule according to claim 37 or claim 38, which, after dilution and dispersion of the WDG in water, as measured by light scattering, has a volume-weighted median particle size of about 1 μm.

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

41. The composition according to claim 40, wherein the additional agroactive compound is a fungicide, an insecticide, a herbicide, an insect killer, a molluscicide, a nematicide, or a combination thereof.

42. The composition according to claim 40 or 41, wherein the additional agroactive compound is a fungicide selected from the group consisting of benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide fungicides, phenylamide fungicides, phosphonate fungicides, cinnamic acid fungicides, oxysterol-binding protein inhibitor (OSBPI) fungicides, triazole carboxamide fungicides, carbamate fungicides, fungicides of family 27, benzamide fungicides, demethylation-inhibiting piperazine fungicides, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, fungicides of family U6, fungicides of family 50, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, fungicides of family 29, thiazolidine fungicides, or combinations thereof.

43. The composition according to any one of claims 40 to 42, wherein the agroactive compound is a fungicide selected from the group consisting of benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, fluopyram, flutolanil, fluxapyroxad, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, fluopyram, azoxystrobin, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluoxastrobin, thifluzamide, cymoxanil, propamocarb, fluopicolide, azoxystrobin, chlorothalonil, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, flusilazole, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, fenpropidin, spiroxamine, cyflufenamid, metrafenone, picoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, orysastrobin, trifloxystrobin, kresoxim-methyl, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dichloran (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram, or combinations thereof.

44. The composition according to any one of claims 40 to 43, wherein the composition further comprises water.

45. The composition according to claim 44, wherein the water-dispersible granules are present in the composition in an amount sufficient to enhance the biological effect of the additional agroactive compound, such that the total amount of the additional agroactive compound in the composition applied to the crop or agricultural product is lower than the amount usually required and / or recommended to provide the same biological effect in a composition not containing the water-dispersible granules.

46. The composition according to claim 45, wherein the additional agroactive compound is a fungicide, insecticide, herbicide, insecticide, molluscicide, nematicide or a combination thereof.

47. The composition according to claim 45 or 46, wherein the additional agroactive compound is a fungicide selected from the group consisting of benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide fungicides, phenylamide fungicides, phosphonate fungicides, cinnamic acid fungicides, oxysterol-binding protein inhibitor (OSBPI) fungicides, triazole carboxamide fungicides, carbamate fungicides, fungicides of group 27, benzamide fungicides, demethylation-inhibiting piperazine fungicides, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, fungicides of group U6, fungicides of group 50, strobilurin fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, QoI fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, fungicides of group 29, thiazolidine fungicides or a combination thereof.

48. The composition according to any one of claims 45 to 47, wherein the additional agroactive compound is a fungicide selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluxametamide, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, prothioconazole, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, amisulbrom, zineb, chlorobenzyl alcohol, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, flusulfamide, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, diclobutrazol, spiroxamine, cyflufenamid, metrafenone, picoxystrobin, azoxystrobin, pyraclostrobin, fluoxastrobin, kresoxim-methyl, pyribencarb, quinoxyfen, Bordeaux, copper ammonium complex, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, calcium polysulfide, mancozeb, maneb, metiram, ferbam, thiram, ziram, dichloran (DCNA), chloroneb, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or a combination thereof.

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

50. A method for controlling or preventing fungal growth, the method comprising applying the composition according to any one of claims 40 to 45 to a site where fungal growth is occurring or is at risk of occurring.

51. A method for controlling or preventing fungal growth, the method comprising: combining the composition according to any one of claims 39 to 40 or 42 to 45 with water to form a fine particle suspension comprising granules of the first agroactive compound; and applying the fine particle suspension to a site where fungal growth is occurring or is at risk of occurring.

52. The method according to claim 51, wherein the method further comprises combining the water-dispersible granule and the additional agroactive compound to form the composition.

53. The method according to claim 52, wherein combining the water-dispersible granule and the agroactive compound comprises adding an amount of the agroactive compound to the water-dispersible granule, the amount being less than the amount of the agroactive compound recommended for use in the absence of the water-dispersible granule.

54. A method for preparing a dispersion, the dispersion comprising the water-dispersible granule according to any one of claims 1 to 39, the method comprising: The water-dispersible granule is combined with water and an additional agroactive compound to provide a mixture, wherein each of the water-dispersible granule and the additional agroactive compound is included at a concentration sufficient to provide a biological effect when the mixture is applied to crops or agricultural products.

55. The method according to claim 54, wherein the concentration of the water-dispersible granule in the mixture ranges from 0.01 wt% to 10 wt%.

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

57. The method according to any one of claims 54 to 56, wherein the additional agroactive compound is selected from acaricides, fungicides, herbicides, insecticides, molluscicides, nematicides or combinations thereof.

58. The method according to any one of claims 54 to 56, wherein the additional agroactive compound is selected from: benzimidazole fungicides, dicarboximide fungicides, phenylpyrrole fungicides, anilinopyrimidine fungicides, hydroxyaniline fungicides, formamide 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, demethylation-inhibiting pyrimidine fungicides, demethylation-inhibiting azole fungicides, morpholine fungicides, U6 Group fungicides, Group 50 fungicides, methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper ammonium complex fungicides, sulfur fungicides, lime sulfur fungicides, ethylenebisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, Qil fungicides, guanidine fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides or combinations thereof.

59. The method according to any one of claims 54 to 58, wherein the additional agroactive compound is selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, metrafenone, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluxametamide, indoxacarb, isofetamid, oxycarboxin, pencycuron, fluopyram, solatenol, metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluazaindolizine, thifluzamide, cymoxanil, propamocarb, fluopicolide, azoxystrobin, chlorothalonil, cyazofamid, polyoxin, fluazinam, fluopyram or a combination thereof.

Images