Oily flowable adenosine triphosphate biphosphatase inhibitor formulations

Abstract

The present disclosure relates to an oily flowable formulation comprising a first active compound # imgabs0 # having structure (I) and a lipophilic solvent, a first dispersant and a rheology modifier. The formulation comprises particles of the first active compound having a median particle size of 0.1 to 20 microns as measured by light scattering. The formulation may further comprise an emulsifier, a second dispersant, and / or an agriculturally active compound such as an acaricide, an antimicrobial agent, a fungicide, a herbicide, an insecticide, a molluscicide, or a nematicide, or a combination thereof. Also disclosed are agricultural compositions comprising the formulations and methods of using the same.

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 / 476,309, filed on December 20, 2022, the entire disclosure of which is incorporated herein by reference. Technical field

[0003] The present disclosure relates to oily flowable adenosine triphosphate diphosphatase inhibitor formulations 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 composition comprising a compound having the following structure:

[0006]

[0007] A lipophilic solvent, a first dispersant, and a rheology modifier. In some embodiments, the compound is substantially insoluble in the lipophilic solvent.

[0008] In some embodiments, the compound is in particulate form, e.g., having a volume - weighted median particle size in the range of greater than 0.01 microns to 40 microns, such as 0.01 microns to 30 microns, 0.01 microns to 25 microns, such as in the range of greater than 0.01 microns to 20 microns, such as 0.1 microns to 5 microns or 0.5 microns to 2 microns, and in certain embodiments, the volume - weighted median particle size is 1 micron. In some embodiments, the particles are present in an amount of 5 wt% to 90 wt%, such as 30 wt% to 85 wt% or 30 wt% to 50 wt%.

[0009] The lipophilic solvent may include mineral oil, fatty acids, vegetable oils or seed oils, terpenes, aliphatic solvents, cyclo - hydrocarbon solvents, aromatic solvents, or their derivatives and / or combinations. In some embodiments, the lipophilic solvent includes fatty acid derivatives. The fatty acid derivatives may be selected from fatty acid esters, fatty acid dialkylamides, and combinations thereof. In some embodiments, the fatty acid derivatives may include oleic acid esters, such as methyl oleate.

[0010] In other embodiments, the lipophilic solvent includes an alkane solvent. And in further embodiments, the lipophilic solvent includes an aromatic solvent and may include tetrahydronaphthalene, alkylated naphthalene, their derivatives, or combinations thereof.

[0011] The rheology modifier may include organically modified clay, silica or hydrophobically modified silica, alumina, polyurethane-based polymers, or combinations thereof. In some embodiments, the rheology modifier is present in an amount of 0.1 wt% to 15 wt%, such as 1 wt% to 10 wt%.

[0012] In any embodiment, the first dispersant has a molecular weight of 1,000 daltons to 100,000 daltons and is completely soluble in the lipophilic solvent. The first dispersant may be present in an amount of 0.1 wt% to 20 wt%, such as 1 wt% to 10 wt%.

[0013] The first dispersant may be an anionic dispersant, a cationic dispersant, a nonionic dispersant, or combinations thereof. In some embodiments, the first dispersant is an anionic dispersant. In other embodiments, the first dispersant is a nonionic dispersant. In some embodiments, the first dispersant is selected from homopolymer dispersants, random or statistical copolymers, block copolymers, or combinations thereof. In certain embodiments, the first dispersant is a copolymer and may be a random or statistical copolymer, a block copolymer, a comb-shaped block copolymer, or combinations thereof.

[0014] In some embodiments, the composition further comprises an emulsifier and a second dispersant. The emulsifier may be an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, an amphoteric surfactant, or combinations thereof and / or may have a molecular weight of 150 daltons to 1,200 daltons.

[0015] In some embodiments, the second dispersant has a molecular weight of 1,000 daltons to 100,000 daltons and / or is soluble in water.

[0016] In some embodiments, the composition comprises no more than 0.1 wt% of compounds including primary amines, secondary amines, and / or tertiary amines.

[0017] In some embodiments, the composition comprises no more than 0.1 wt% of quaternary ammonium compounds.

[0018] In any embodiment, the composition may further comprise an agricultural active compound.

[0019] Also disclosed is an embodiment of an agricultural composition, which comprises water and / or a lipophilic solvent and the compositions disclosed herein, such as 0.01 wt% to 10 wt% of the compositions disclosed herein. A method of using the agricultural composition is also disclosed. The method may include applying the agricultural composition to a plant, a part of a plant, a seed, the soil in which a plant is growing or will grow, or the soil in which a seed has been or will be sown.

[0020] Also disclosed is a method of using the disclosed composition or its agricultural composition to control or prevent fungal growth.

[0021] The foregoing and other objects, features and advantages of the present invention will become more apparent from the following detailed description. Detailed Description

[0022] I. Terms

[0023] The following explanations of terms and methods are provided to better describe the present disclosure and to guide one of ordinary skill in the art in practicing the present disclosure. Unless the context clearly dictates otherwise, the singular forms "a", "an" and "the" are intended to mean one or more than one. Unless the context clearly dictates otherwise, the term "or" means a single element of the recited 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. All references (including patents and patent applications) cited herein are incorporated by reference in their entirety unless otherwise indicated.

[0024] Unless otherwise indicated, all numerical values expressing quantities of components, molecular weights, percentages, temperatures, times, etc. used in the specification or claims should be understood to be modified by the term "about". Thus, unless otherwise implied 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 embodiments are directly and explicitly distinguished from the prior art being discussed, the embodiment numerical values are not approximations unless the word "about" is explicitly recited.

[0025] 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, the appropriate methods and materials are described below. These materials, methods, and examples are illustrative only and are not intended to be limiting.

[0026] "Application" means any suitable mode of application for controlling pathogens such as fungal pathogens, including treating existing crops, agricultural products, seeds, soil, or combinations thereof.

[0027] "In combination with" means applying the compounds either simultaneously in a single application or sequentially in two or more different applications that may be separated in time, location, or method.

[0028] "Control" with respect to pathogens such as fungal pathogens means blocking, inhibiting, and / or eradicating the pathogens and / or preventing the pathogens from damaging the crop. In one embodiment, control means reducing one or more pathogens such as fungi to undetectable levels, or reducing or inhibiting fungal pathogens 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 many 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.

[0029] As used herein, the terms "enhancer" and "synergist" mean one or more compounds that enhance the effect 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 compounds of the invention inhibit the enzymatic activity of adenosine triphosphate diphosphatase, 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, strengthened, or synergized. For example, when an enhancer or synergist 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 fungi resistant to the fungicide sensitive due to the activity of the enhancer. Most commonly, these enhancers or synergists themselves do not inhibit pathogens such as fungi per se and do not have a harmful effect on living organisms that are (or may be) infected by the pathogens.

[0030] As used herein, the term "treatment" refers to a method for applying or administering an effective amount of the disclosed compound or its formulation to a target area of a field and / or a plant. Treatment methods can include, but are not limited to, aerosol spraying, pressure spraying, direct watering, chemigation, atomization, and dipping. Target areas of a plant can 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 can include methods in which one area of the plant (e.g., the root zone or the leaf surface) is treated and another area of the plant is protected (e.g., protecting the leaf surface when the disclosed compound is applied to the root zone, or protecting new growth when the disclosed compound is applied to the leaf surface).

[0031] As used herein, the terms "oily flowability", "oil miscible flowable concentrate", "oil miscible suspension", or "OF" refer to liquid formulations containing a stable suspension of the active ingredient in oil. Oily flowable formulations can be stored and can be provided to the market and / or the end user without further processing. In actual use, an oily flowable formulation is prepared for application by the end user. Generally, the oily flowable formulation is mixed with water and / or a lipophilic solvent in the end user's spray tank to an appropriate dilution for a particular application. The dilution may vary depending on factors such as the crop, the pathogen, the particular time of year, the geographical location, local regulations, and the intensity of the infestation. After being appropriately diluted, the formulation can be applied, for example, by spraying.

[0032] II. Formulations

[0033] A common goal of formulators of agricultural products is to maximize the biological activity of the active ingredient. In suspension formulations, this is particularly challenging because the solid state of the active ingredient tends to limit bioavailability. However, when delivered as a suspension, it is generally not possible to predict whether a particular active ingredient will have good biological activity. Without being limited by a theoretical understanding, factors that can determine biological activity include solubility in water (including how it varies with temperature, salinity, and pH at the application site), solubility in hydrophobic regions (including within the waxy leaf cuticle and any micellar surfactant domains), lattice energy, the density of the active ingredient crystals and thus their sedimentation tendency, the presence of crystal polymorphs and metastable states, diffusivity in water, the ability of the active ingredient to diffuse through the plant cuticle, the location of the site where the active ingredient acts, and the concentration of the active ingredient required at that site of action. It is possible for formulators to discover 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.

[0034] Among the formulations tested during the work described in the present disclosure, the inventors have found that oily flowable formulations of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally have poor biological activity. It has further been found that for formulations containing the desired components described herein, by controlling the particle size within a specific size range, the biological activity is greatly enhanced.

[0035] 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 physical stability (meaning that in the common product containers in which the product is 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 a variety of 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 for the active ingredient to be autocatalytic so that 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 susceptibility. 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 on a larger scale in commercial applications.

[0036] Among the formulations tested during the work described in the present disclosure, the inventors have found that aqueous suspensions of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide generally have unacceptable chemical stability. However, it has been found that the oily flowable formulations described herein and containing the disclosed desired components have sufficient physical stability and remain 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).

[0037] Disclosed herein is an oily flowable formulation comprising a first active compound having the following structure

[0038]

[0039] (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0040] In some embodiments, the oily flowable formulation further comprises a lipophilic solvent, a first dispersant, and a rheology modifier. In some embodiments, the oily flowable formulation is an oil-miscible concentrate suitable for dilution, for example, by the end user.

[0041] In some embodiments, the first active compound is present in the formulation as a suspension. As determined by light scattering, the suspended particles can have a volume-weighted median particle size in the range of greater than 0.01 microns to 40 microns, such as 0.01 microns to 30 microns, 0.01 microns to 25 microns, such as greater than 0.01 microns to 20 microns, 0.01 microns to 15 microns, 0.01 microns to 10 microns, such as 0.1 microns to 5 microns or 0.5 microns to 2 microns. In certain embodiments, the volume-weighted median particle size is 1 micron. In certain other embodiments, the volume-weighted median particle size is 7.0 microns. In other embodiments, the volume-weighted median particle size is 15 microns. Additionally, if the formulation contains additional suspending materials such as those disclosed herein, any such additional suspending materials can also have a particle size as measured by light scattering as disclosed above for the first active compound.

[0042] A. First active compound

[0043] The oily flowable formulation contains the first active compound (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide in an amount sufficient such that when used diluted, the first active compound is present in an amount sufficient to enhance the efficacy of one or more agroactive compounds that can be applied in combination with the first active compound. In some embodiments, the oily flowable formulation contains 5 wt% to 90 wt% of the first active compound, such as 10 wt% to 90 wt%, 20 wt% to 90 wt%, 30 wt% to 85 wt%, 30 wt% to 75 wt%, 30 wt% to 65 wt%, 30 wt% to 50 wt% or 30 wt% to 40 wt% of the first active compound.

[0044] B. Lipophilic solvent

[0045] In some embodiments, the lipophilic solvent is or comprises a mineral oil, a fatty acid, a vegetable oil or seed oil, a terpene, an aliphatic solvent, a cycloaliphatic solvent, an aromatic solvent or their derivatives and / or combinations. In certain embodiments, the lipophilic solvent is or comprises a fatty acid derivative, such as methyl oleate, methyl linoleate or a combination thereof, for example ME. In some embodiments, the lipophilic solvent is or comprises an alkane solvent, such as Exxsol TM D80, Exxsol TM D110 or Exxsol TM D130 alkane solvent. In some embodiments, the lipophilic solvent is or comprises an aromatic solvent, such as Solvesso TM Aromatic solvent, such as Solvesso TM 200ND or Solvesso TM150 ND. In some embodiments, the lipophilic solvent is or comprises tetrahydronaphthalene, alkylated naphthalene, their derivatives, and / or combinations thereof.

[0046] In some embodiments, the lipophilic solvent is selected such that the first active compound is substantially insoluble therein. In some embodiments, the solubility of the first active compound in the lipophilic solvent under ambient conditions is less than 2 wt%, such as the solubility in the lipophilic solvent being from 0 to 2 wt%, from 0 to 1 wt%, or from 0 to 0.1 wt%. Those of ordinary skill in the art understand that the solubility of a compound in an organic solvent can be determined by conventional techniques known to those of ordinary skill in the art.

[0047] C. Rheology modifier

[0048] In some embodiments, the rheology modifier is or comprises an organically modified clay, silica, or hydrophobically modified silica, alumina, a polyurethane-based polymer, or combinations thereof. In some embodiments, the rheology modifier is or comprises an organically modified clay, such as a magnesium aluminum silicate hydrate salt, for example 50. In some embodiments, the rheology modifier is or comprises a hydrophobically modified ethoxylated urethane copolymer, for example Gel 0434.

[0049] The rheology modifier is present in an amount suitable to provide desired properties, such as a specific viscosity. In some embodiments, the rheology modifier is present in the formulation in an amount of 0.1 wt% to 15 wt%, such as 1 wt% to 10 wt%.

[0050] D. First dispersant

[0051] The first dispersant may have a molecular weight of 1,000 daltons to 100,000 daltons or greater. In some embodiments, the first dispersant is completely soluble in the lipophilic solvent. In some embodiments, the first dispersant is or comprises a copolymer, a homopolymer, or combinations thereof. The copolymer may be a random or statistical copolymer, a block copolymer, a comb-shaped block copolymer, or combinations thereof. Exemplary first dispersants include, but are not limited to, polyvinylpyrrolidone; a random copolymer of a combination of vinylpyrrolidone, stearyl methacrylate, lauryl methacrylate, and / or butyl methacrylate; a block copolymer of ethylene oxide and propylene oxide; or combinations thereof.

[0052] The first dispersant may be present in the formulation in an amount of 0.1 wt% to 20 wt%, such as 1 wt% to 10 wt%.

[0053] E. Emulsifier

[0054] Optionally, the oily flowable formulation further comprises an emulsifier. The emulsifier can be an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium surfactant, an amphoteric surfactant, or a combination thereof. In some embodiments, the surfactant is an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof. In any embodiment, the emulsifier can have a molecular weight of 150 Daltons to 1,200 Daltons.

[0055] In any embodiment, the anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate. The anionic surfactant can be an ester of an alcohol, an alcohol alkoxylate (such as an alcohol ethoxylate and / or an alcohol propoxylate), a tristyrylphenol ethoxylate, a fatty acid, a natural oil, or a combination thereof. In other embodiments, the anionic surfactant can be a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate, such as a calcium salt, a sodium salt, a potassium salt, a lithium salt, an organic amine salt, or an ammonium salt.

[0056] In certain embodiments, the organic amine salt is a salt of isopropylamine, butylamine, ethylamine, diethylamine, triethylamine, diethanolamine, triethanolamine, methylamine, ethylenediamine, or a combination thereof.

[0057] In certain embodiments, the anionic surfactant is a citrate ester, carboxylate ester, phosphate ester, phosphonate ester, sulfate ester, or sulfonate ester of an alcohol, an alcohol alkoxylate, a tristyrylphenol ethoxylate, a fatty acid, a natural oil, or any combination thereof. Exemplary anionic surfactants are ABS 60C-EH, which comprises calcium dodecylbenzenesulfonate.

[0058] The cationic surfactant can be an ethoxylated amine, such as an ethoxylated amine of a natural oil, an alcohol, a fatty acid, or a combination thereof.

[0059] In some embodiments, the formulation comprises no more than 0.1 wt% of a compound comprising a primary amine, a secondary amine, and / or a tertiary amine, such as 0 to 0.1 wt% of such a compound, or 0 wt% of such a compound. In some embodiments, the formulation comprises no more than 0.1 wt% of a compound comprising a quaternary ammonium compound, such as 0 to 0.1 wt% of such a compound, or 0 wt% of such a compound. In some such embodiments, the anionic surfactant can be a citrate, carboxylate, phosphate, phosphonate, sulfate, or sulfonate, such as a calcium salt, a sodium salt, a potassium salt, or a lithium salt.

[0060] The nonionic surfactant can be an alkoxylate of an alcohol, a natural oil, a fatty alcohol, or a combination thereof, such as an ethoxylate and / or a propoxylate of an alcohol, a natural oil, a fatty alcohol, or a combination thereof. Exemplary nonionic surfactants are LF 700, which is an alkoxylated fatty alcohol.

[0061] The quaternary ammonium surfactant may comprise 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.

[0062] And in some embodiments, the zwitterionic surfactant comprises 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 cocamidopropyl betaine.

[0063] In other embodiments, the surfactant is a non-ionic surfactant and may be selected from alkoxylates of alcohols, natural oils, or combinations thereof.

[0064] Particularly with respect to the surfactants disclosed herein, those of ordinary skill in the art will understand that the alkoxylate group (e.g., ethoxylate or propoxylate) may comprise one or more alkoxy moieties (i.e., may 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.

[0065] F. Second Dispersant

[0066] Optionally, the oily flowable formulation further comprises a second dispersant. The second dispersant may be an anionic dispersant, a cationic dispersant, a non-ionic dispersant, or a combination thereof. The second dispersant may have a molecular weight of 1,000 Daltons to 100,000 Daltons. In some embodiments, the second dispersant is water-soluble. In some embodiments, the second dispersant is or comprises a homopolymer dispersant, a random or statistical copolymer, a block copolymer, or a combination thereof. In some embodiments, the second dispersant is selected from polyacrylic acid, polyvinyl alcohol, polyvinylpyrrolidone, polystyrene sulfonate, 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.

[0067] In certain embodiments, the second dispersant is an anionic dispersant.

[0068] In other embodiments, the second dispersant is a non-ionic dispersant.

[0069] In some embodiments, the oily flowable formulation comprises both an emulsifier and a second dispersant.

[0070] III. Agricultural active compounds

[0071] The disclosed formulations may also contain agricultural active compounds. In addition or alternatively, the formulations 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 dilution composition that is formed at least in part by diluting the disclosed formulation with a suitable solvent or solvent mixture (such as water and / or a lipophilic solvent as described above).

[0072] Embodiments of the disclosed formulations can be used to enhance the effectiveness of a variety of agrochemicals, including fungicides, antivirals, bactericides, herbicides, insect / acaricides, molluscicides, nematicides, soil insecticides, plant protectants, synergists, fertilizers, and soil conditioners, such as fungicides, insecticides, herbicides, insecticides, molluscicides, nematicides, or combinations thereof.

[0073] In one embodiment, the formulations disclosed herein can be used to enhance the fungicidal action of a variety of fungicides. Fungicides used in combination with the disclosed formulations are well known to those skilled in the art and include, but are not limited to, those listed by category in Table 1:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] Fungicides are more generally catalogued by the Fungicide Resistance Action Committee (FRAC) in the FRAC Code List 2022 and reproduced in Appendix 1, which is hereby incorporated by reference in its entirety.

[0080] In one embodiment, the disclosed formulation is used in combination with one or more compounds from the categories or groups listed in Table 1, Appendix 1, or both. In certain embodiments, the formulation is used in combination with one or more fungicides listed in column 1 of Table 1.

[0081] In certain embodiments, the disclosed formulations are used in combination with a fungicide selected from one or more of the following: benzimidazoles, dicarboximides, phenylpyrroles, anilinopyrimidines, hydroxyanilines, formamides, phenylamides, phosphonates, cinnamic acids, oxysterol binding protein inhibitors (OSBPIs), triazole carboxamides, cymoxanil, carbamates, benzamides, demethylation-inhibiting piperazines, demethylation-inhibiting pyrimidines, demethylation-inhibiting azoles (including imidazoles and triazoles such as cyproconazole, difenoconazole, myclobutanil, flutriafol, fludioxonil, metconazole, ipconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole), morpholines, cyflufenamid, metrafenone, fenpyrazamine, strobilurins, copper ammonium complexes, copper hydroxide, copper oxide, copper oxychloride, copper sulfate, sulfur, lime sulfur, ethylene bisdithiocarbamates, aromatic hydrocarbons, phthalimides, guanidines, polyoxins, fluazinam, and thiazolanes.

[0082] Certain fungicides enhanced by the method herein through the use of an apyrase inhibitor in combination with the disclosed formulations are copper (such as copper octanoate, copper hydroxide, copper sulfate, etc.), myclobutanil, propiconazole, tebuconazole, epoxiconazole, difenoconazole, triticonazole, and prothioconazole.

[0083] In one embodiment, treatment with a combination of a selected fungicide and the disclosed formulation provides synergistic fungicidal activity against phytopathogenic fungi.

[0084] In one embodiment, the present disclosure provides compositions and methods for treating plants or plant seeds infected or at risk of being infected by fungal pathogens. In one embodiment, the compositions of the present disclosure comprise a formulation of a fungicide, the disclosed formulation, and a botanically acceptable carrier. In another embodiment, the fungicide and the formulation are applied in separate compositions. In additional embodiments, agricultural or horticultural fungicides are used in combination with other compounds in addition to the disclosed formulation. Such other compounds may be applied in the same or separate compositions as the fungicide and / or the formulation. Examples of other components include known carriers for formulation. Additional examples thereof include conventionally known herbicides, insecticide / acaricides, nematicides, soil insecticides, plant protectants, synergists, fertilizers, soil conditioners, and animal feeds. In one embodiment, the inclusion of such other components produces a synergistic effect on crop growth.

[0085] In one embodiment, the disclosed formulation 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 formulation include acetyl-CoA synthase inhibitors, acetolactate synthase inhibitors, microtubule assembly inhibitors, microtubule organizing inhibitors, auxin mimics, photosynthesis inhibitors, deoxy-D-xylulose phosphate synthase inhibitors, enolpyruvate shikimate 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, and / or lycopene cyclase inhibitors.

[0086] In one embodiment, the disclosed formulation is used to enhance the action of insecticides. Exemplary insecticides for use in combination with the disclosed formulation are known to those skilled in the art and include, but are not limited to, those described in Appendix 3.

[0087] IV. Methods of Using the Formulation

[0088] Embodiments of the method of using the disclosed formulation include diluting the formulation in a suitable diluent such as water and / or a lipophilic solvent 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 further 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.

[0089] In some embodiments, the disclosed formulation comprises one or more agroactive compounds, and the agricultural composition is formed by diluting the formulation to a concentration suitable for agricultural application with a suitable solvent such as water and / or a lipophilic solvent. Optionally, one or more additional agroactive compounds may be added before, during, and / or after diluting the formulation.

[0090] In other embodiments, the formulation does not comprise agroactive compounds, and the agricultural composition is formed by diluting the formulation in a suitable solvent such as water and / or a lipophilic solvent to a concentration suitable for agricultural use. In such embodiments, forming the agricultural composition may further include adding one or more agroactive compounds to the water and / or lipophilic solvent, then adding the formulation while diluting the formulation with water and / or a lipophilic solvent, and / or subsequently adding one or more agroactive compounds to the diluted mixture containing the formulation.

[0091] In certain non-limiting embodiments, the disclosed formulations are diluted to provide an amount of the first active compound sufficient for agricultural applications in an amount of 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. In one embodiment, the first active compound is provided in an amount of from 0.01 to 50% in the final diluted composition, 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.

[0092] In some embodiments, the agroactive compound is present in the agricultural composition at a concentration less than the concentration of the agroactive compound recommended for use in the absence of the formulations disclosed herein, such as in the absence of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide.

[0093] In some embodiments, the method of preparing the agricultural composition comprises adding the formulations disclosed herein to water and / or a lipophilic solvent in an amount sufficient to enhance the agroactive compound, and adding the agroactive compound in an amount sufficient to provide a concentration in the agricultural composition that is less than the concentration recommended for use in the absence of the disclosed formulations, 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 formulations and the agroactive compound can be added to water and / or a lipophilic solvent in any order, sequentially or substantially simultaneously, to form the agricultural composition.

[0094] In any embodiment, the one or more agroactive compounds can be agricultural or horticultural insecticides as disclosed herein, such as acaricides, antimicrobials, fungicides, herbicides, insecticides, molluscicides or nematicides or combinations thereof. In some embodiments, the method is a method for controlling or preventing fungal growth.

[0095] As is known to those of ordinary skill in the agricultural arts, the treatable crops include crops infected by various pathogens, including but not limited to bacteria, viruses, fungal pathogens, mites, nematodes, mollusks, weeds, or other pests. By way of example, such agricultural and horticultural crops that can be treated in accordance with 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, for example banana trees, tea trees, coffee trees, or cocoa trees; grasses; turfgrasses; or cotton.

[0096] The agricultural compositions containing the disclosed formulations can be applied to every part of the plant, such as leaves, stems, patterns, flowers, flower buds, fruits, seeds, seedlings, roots, tubers, rhizomes, buds, or cuttings. The formulations can also be applied to improved varieties, cultivars, and mutants, hybrids, and genetically modified embodiments of these plants.

[0097] The agricultural compositions containing the disclosed formulations 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).

[0098] The agricultural compositions containing the disclosed formulations can be used to enhance the action of antimicrobials. For example, the disclosed formulations can be used in combination with antimicrobials to combat bacterial and viral infections.

[0099] Embodiments of the disclosed formulations can be used to enhance the action of herbicides. For example, the disclosed formulations can be used in combination with one or more herbicides to control weeds or other unwanted vegetation.

[0100] Embodiments of the disclosed formulations can be used to enhance the action of insecticides. For example, the disclosed formulations can be used in combination with one or more insecticides to control insect pests.

[0101] Embodiments of the disclosed formulations can be used to enhance the action of acaricides or miticides. For example, the disclosed formulations can be used in combination with one or more acaricides to control mites.

[0102] Embodiments of the disclosed formulations can be used to enhance the action of molluscicides. For example, the disclosed formulations can be used in combination with one or more molluscicides to prevent slugs or snails from disturbing the crops.

[0103] Embodiments of the disclosed formulations can be used to enhance the action of nematicides. For example, the disclosed formulations can be used in combination with one or more nematicides to prevent nematodes from disturbing the crops.

[0104] Embodiments of the disclosed formulations 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.

[0105] Botrytis cinerea is an airborne plant pathogen with a necrotrophic lifestyle that attacks over 200 crop hosts worldwide. It primarily 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 are ineffective against Botrytis cinerea due to its genetic plasticity.

[0106] The genus Colletotrichum includes approximately 600 species that attack over 3,200 monocotyledonous and dicotyledonous plant species. Colletotrichum graminicola primarily infects maize (Zea mays) and causes losses of approximately $1 billion per year in the United States alone (Connell et al., 2012).

[0107] Banana wilt, caused by the soil-borne fungus Fusarium oxysporum f.sp. cubense, is a major threat to banana production worldwide. Currently, there are no fungicides available to effectively control the disease after the plant is infected (Peng J et al., 2014).

[0108] The white mold Sclerotiana sclerotiorum is known to attack over 400 host species and is considered one of the most prolific plant pathogens. Most infected crop species are dicotyledonous, as well as some agriculturally important monocotyledonous plants. Some important crops infected by Sclerotiana include legumes (soybeans), most vegetables, stone fruits, and tobacco.

[0109] The ascomycete Verticillium dahlia is a soil-borne fungal plant pathogen that causes vascular wilt in a wide range of dicotyledonous host species. Verticillium dahlia can cause severe yield and quality losses in cotton and other important crops such as vegetables, fiber, fruits, nut trees, forest trees, and ornamental plants.

[0110] The ascomycete fungus Septoria tritici blotch (anamorph: Septoria tritici) is one of the most important foliar diseases of wheat, occurring 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.

[0111] The basidiomycete fungus Sphacelotheca reiliana systemically infects maize (Zea mays), causing head smut. The yield losses caused by this disease are variable and depend directly on the incidence of the disease. The fungus overwinters in the form of diploid teliospores in crop debris or soil. The flower structure is transformed into a sorus containing a large amount of powdery teliospores, similar to the mature gall of common smut.

[0112] Examples of crops and plant diseases (pathogens) controlled by treating with the compounds and compositions disclosed by the present invention include, but are not limited to:

[0113] Beet: Cercospora leaf spot (Cercospora beticola), black root rot (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc.

[0114] Peanut: Brown leaf 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.

[0115] Cucumber: 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), angular leaf spot (Cladosporium cucumerinum), brown spot (Coryn espora cassiicola), damping-off (Pythium debaryanum, Rhizoctonia so lani Kuhn), Phomopsis root rot of cucumber (Phomopsis sp., Pseudomonas syringae pv. Lechrymans), etc.

[0116] Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporiumfulvum), late blight (Phytophthora infestans), Verticillium wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), early blight (Alternaria solani), leaf mold (Pseudocercospora fuligena), etc.

[0117] Eggplant: Gray mold (Botrytis cinerea), black rot (Corynespora melo ngenae), powdery mildew (Erysiphe cichoracearum), leaf mold (Mycovellosiellanattrassii), sclerotinia rot (Sclerotinia sclerotiorum), Verticillium wilt (Verticillium dahliae), Phomopsis blight (Phomopsisvexans), etc.

[0118] Strawberries: Gray mold (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.

[0119] Onions: Neck rot (Botrytis allii), gray mold (Botrytis cinerea), leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor), Phytophthora porn disease (Phytophthora porn), etc.

[0120] Cabbages: Clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. Campestris), bacterial black spot (Pseudomonas syringae pv. Maculicola, P. s. pv. Alisalensis), downy mildew (Peronospora parasitica), sclerotinia rot (Sclerotinia sclerotiorum), black spot (Alternaria brassicicola), gray mold (Botrytis cinerea), etc.

[0121] Common beans: Sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular leaf spot (Phaeoisariopsis griseola), etc.

[0122] Apple: Powdery mildew (Podosphaera leucotricha), Scab (Venturia inaequalis), Brown rot (Monilia mali), Black spot (Mycosphaerella pomi), Canker (Valsa mali), Alternaria blotch (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.

[0123] Japanese apricot: Scab (Cladosporium carpophilum), Gray mold (Botrytis cinerea), Brown rot (Monilinia mumecola), etc.

[0124] Persimmon: Powdery mildew (Phyllactinia kakicola), Anthracnose (Gloeosporium kaki), Angular leaf spot (Cercospora kaki), etc.

[0125] Peach: Brown rot (Monilinia fructicola), Scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), Bacterial shot hole (Xanthomonas campestris pv. Pruni), etc.

[0126] Apricots: Brown rot (Monilinia taxa), Spot anthracnose (Stigminacarpophila), Scab (Cladosporium carpophilum), Red leaf spot (Polystigma rubrum), Alternaria leaf spot (Alternaria alternata), Anthracnose (Colletotrichum gloeospoides), etc.

[0127] Yellow peaches: Brown rot (Monilinia fructicola), Anthracnose (Colletotrichum acutatum), Black spot (Alternaria sp.), Sclerotinia rot of young fruits (Monilinia kusanoi), etc.

[0128] Grapes: Gray mold (Botrytis cinerea), Powdery mildew (Uncinula necator), ripe 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.

[0129] Pears: 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.

[0130] Tea: Target spot (Pestalotiopsis longiseta, Pestalotiopsis theae), Anthracnose (Colletotrichum theae-sinensis), Net blight (Exobasidium reticulatum), etc.

[0131] Citrus fruits: black spot (Elsinoe fawcettii), blue mold (Penicillium italicum), common green mold (Penicillium digitatum), gray mold (Botrytis cinerea), melanose (Diaporthe citri), powdery mildew (Oidium sp.), etc.

[0132] 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), spot blotch (Typhula incarnata), sclerotial snow blight (Myriosclerotinia borealis), damping-off (Gaeumannomyces graminis), ergot (Claviceps purpurea), bunt (Tilletia caries), loose smut (Ustilago nuda), etc.

[0133] Barley: leaf spot (Pyrenophora graminea), net blotch (Pyrenophora teres), leaf spot (Rhynchosporium secalis), loose smut (Ustilago tritici, U. nuda), etc.

[0134] 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), Rice brown spot (Alternaria, Curvularia intermedia), Discoloration of rice grains (Alternaria padwickii), Powdering of rice grains (Epicoccum purpurascens), etc.

[0135] Tobacco: Sclerotinia rot (Sclerotinia sclerotiorum), Powdery mildew (Erysiphe cichoracearum), Phytophthora rot (Phytophthora nicotianae), etc.

[0136] Tulip: Botrytis blight (Botrytis cinerea), etc.

[0137] Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia rot (Sclerotinia sclerotiorum), etc.

[0138] Evergreen grass: Sclerotinia snow blight (Sclerotinia borealis), Giant leaf spot (Rhizoctonia solani), Brown spot (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.), Pythium blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc.

[0139] Orchard grass: Powdery mildew (Erysiphe graminis), etc.

[0140] Soybeans: Purple spot (Cercospora kikuchii), downy mildew (Peronospora manshurica), Phytophthora rot (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotinia rot (Sclerotinia sclerotiorum), anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), citrus scab (Elsinoe glycines), black rot (Diaporthe phaseolorum var. sojae), etc.

[0141] Potatoes: Phytophthora rot (Phytophthora infestans), early blight (Alternaria solani), scurf (Rhizoctonia solani), Verticillium wilt (Verticillium albo - atrum, Verticillium dahliae, Verticillium nigrescens, etc.).

[0142] Bananas: Panama disease (Fusarium oxysporum), banana leaf spot (Mycosphaerella fijiensis, Mycosphaerella musicola), etc.

[0143] Rapeseed: Sclerotinia rot (Sclerotinia sclerotiorum), root rot (Phoma lingam), black leaf spot (Alternaria brassicae), etc.

[0144] Coffee: Rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), leaf spot (Cercospora coffeicola), etc.

[0145] Sugarcane: Brown rust (Puccinia melanocephala), etc.

[0146] 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.

[0147] Cotton: seedling blight (Pythium sp.), rust (Phakopso ragossypii), sour rot (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.

[0148] V. Methods for Preparing Formulations

[0149] The disclosed formulations can be prepared by methods known to those of ordinary skill in the art. In some embodiments, the method includes providing a first active compound, a lipophilic solvent, a dispersant, and a rheological modifier, and forming the formulation. Optionally, an emulsifier, a second dispersant, and / or an agroactive compound can also be added. In some embodiments, the first active compound is first milled (such as by stirring with beads) to a desired particle size such as a median particle size of less than 2 microns and used to form the formulation. In some embodiments, the milled first active compound is added to a mixture comprising a lipophilic solvent, a first dispersant, and a rheological modifier. In other embodiments, the milled first active compound is added to one or more of a lipophilic solvent, a first dispersant, and a rheological modifier, and the remaining components are added subsequently or simultaneously.

[0150] In any embodiment, any optional components, such as an emulsifier and / or a second dispersant and any agroactive compound, can be added at any suitable stage during formulation formation.

[0151] In other embodiments, the first active compound is added to one or more of a lipophilic solvent, a first dispersant, and a rheological modifier, then milled (such as by stirring with beads) to a desired particle size, and then any remaining components are added. If an optional emulsifier and / or a second dispersant are needed, they can be added before, after, or during milling the first active compound. Similarly, any agroactive compound can be added at any suitable stage during formulation formation.

[0152] In any embodiment, the mixture comprising the rheological modifier can be subjected to high shear to actively activate the rheological modifier. As understood by those of ordinary skill in the art, the mixture can be exposed to high shear at any suitable stage during formulation formation.

[0153] VI. Certain Embodiments

[0154] The present disclosure contemplates the following numbered embodiments and so on:

[0155] 1. A composition, the composition comprising:

[0156] A compound having the following structure

[0157]

[0158] A lipophilic solvent;

[0159] A first dispersant; and

[0160] A rheology modifier.

[0161] 2. The composition according to embodiment 1, wherein the compound is substantially insoluble in the lipophilic solvent.

[0162] 3. The composition according to embodiment 1 or embodiment 2, wherein the compound is present in particulate form, and the particles have a volume-weighted median particle size in the range of greater than 0.01 μm to 20 μm.

[0163] 4. The composition according to embodiment 3, wherein the volume-weighted median particle size is 0.1 μm to 5 μm.

[0164] 5. The composition according to embodiment 1, wherein the volume-weighted median particle size of the compound is less than about 15 μm as measured by light scattering.

[0165] 6. The formulation according to embodiment 1, wherein the volume-weighted median particle size of the compound is less than about 7 μm as measured by light scattering.

[0166] 7. The composition according to embodiment 3, wherein the volume-weighted median particle size is 0.5 μm to 2 μm.

[0167] 8. The formulation according to embodiment 1, wherein the volume-weighted median particle size of the compound is about 1 μm or less as measured by light scattering.

[0168] 9. The composition according to any one of embodiments 1 to 8, wherein the lipophilic solvent comprises mineral oil, fatty acid, vegetable oil or seed oil, terpene, aliphatic solvent, cycloaliphatic solvent, aromatic solvent or their derivatives and / or combinations.

[0169] 10. The composition according to embodiment 9, wherein the lipophilic solvent comprises fatty acid derivatives.

[0170] 11. The composition according to embodiment 10, wherein the fatty acid derivatives are selected from fatty acid esters, fatty acid dialkylamides and combinations thereof.

[0171] 12. The composition according to embodiment 10, wherein the fatty acid derivative comprises methyl oleate.

[0172] 13. The composition according to embodiment 9, wherein the lipophilic solvent comprises an alkane solvent.

[0173] 14. The composition according to embodiment 9, wherein the lipophilic solvent comprises an aromatic solvent.

[0174] 15. The composition according to embodiment 9, wherein the lipophilic solvent comprises tetralin, alkylated naphthalene, their derivatives or a combination thereof.

[0175] 16. The composition according to any one of embodiments 3 to 8, wherein the particles are present in an amount of 5 wt% to 90 wt%.

[0176] 17. The composition according to any one of embodiments 3 to 8, wherein the particles are present in an amount of 30 wt% to 85 wt%.

[0177] 18. The composition according to any one of embodiments 3 to 8, wherein the particles are present in an amount of 30 wt% to 50 wt%.

[0178] 19. The composition according to any one of embodiments 1 to 18, wherein the rheology modifier comprises organically modified clay, silica or hydrophobically modified silica, alumina, polyurethane-based polymers or a combination thereof.

[0179] 20. The composition according to any one of embodiments 1 to 19, wherein the rheology modifier is present in an amount of 0.1 wt% to 15 wt%.

[0180] 21. The composition according to embodiment 20, wherein the rheology modifier is present in an amount of 1 wt% to 10 wt%.

[0181] 22. The composition according to any one of embodiments 1 to 21, wherein the first dispersant has a molecular weight of 1,000 to 100,000 daltons and is completely soluble in the lipophilic solvent.

[0182] 23. The composition according to any one of embodiments 1 to 22, wherein the first dispersant is an anionic dispersant, a cationic dispersant, a non-ionic dispersant or a combination thereof.

[0183] 24. The composition according to any one of embodiments 1 to 23, wherein the first dispersant is an anionic dispersant.

[0184] 25. The composition according to any one of embodiments 1 to 23, wherein the first dispersant is a non-ionic dispersant.

[0185] 26. The composition according to any one of embodiments 1 to 25, wherein the first dispersant is selected from homopolymer dispersants, random or statistical copolymers, block copolymers, or combinations thereof.

[0186] 27. The composition according to any one of embodiments 1 to 25, wherein the first dispersant is a copolymer.

[0187] 28. The composition according to embodiment 27, wherein the copolymer is a random or statistical copolymer, a block copolymer, a comb-shaped block copolymer, or combinations thereof.

[0188] 29. The composition according to any one of embodiments 1 to 26, wherein the first 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 combinations thereof.

[0189] 30. The composition according to any one of embodiments 1 to 29, wherein the first dispersant is present in an amount of 0.1 wt% to 20 wt%.

[0190] 31. The composition according to embodiment 30, wherein the first dispersant is present in an amount of 1 wt% to 10 wt%.

[0191] 32. The composition according to any one of embodiments 1 to 31, the composition further comprising an emulsifier and a second dispersant.

[0192] 33. The composition according to embodiment 32, wherein the emulsifier has a molecular weight of 150 daltons to 1,200 daltons.

[0193] 34. The composition according to embodiment 32 or embodiment 33, wherein the emulsifier is an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium salt surfactant, an amphoteric surfactant, or combinations thereof.

[0194] 35. The composition according to embodiment 34, wherein the emulsifier is selected from anionic surfactants, cationic surfactants, nonionic surfactants, or combinations thereof.

[0195] 36. The composition according to embodiment 34 or embodiment 35, wherein:

[0196] The anionic surfactant is a citrate, carboxylate, phosphate, phosphonate, sulfate or sulfonate ester of an alcohol, an alcohol ethoxylate, a tristyrylphenol ethoxylate, a fatty acid or a natural oil or any combination thereof;

[0197] The cationic surfactant is an ethoxylated amine of a natural oil, an alcohol, a fatty acid or a combination thereof; or

[0198] The nonionic surfactant is a polyethoxylated and / or polypropoxylated product of an alcohol, a natural oil or a combination thereof.

[0199] 37. The composition according to any one of embodiments 1 to 36, wherein the composition comprises no more than 0.1 wt% of a compound comprising a primary amine, a secondary amine and / or a tertiary amine.

[0200] 38. The composition according to any one of embodiments 1 to 37, wherein the composition comprises no more than 0.1 wt% of a quaternary ammonium compound.

[0201] 39. The composition according to any one of embodiments 32 to 38, wherein the second dispersant has a molecular weight of 1,000 to 100,000 daltons and is soluble in water.

[0202] 40. The composition according to any one of embodiments 1 to 39, the composition further comprising an agricultural active compound A.

[0203] 41. An agricultural composition, the agricultural composition comprising water and / or a lipophilic solvent and the composition according to any one of embodiments 1 to 40.

[0204] 42. The agricultural composition according to embodiment 41, wherein the agricultural composition comprises 0.01 wt% to 10 wt% of the composition according to any one of embodiments 1 to 40.

[0205] 43. The agricultural composition according to embodiment 41 or embodiment 42, wherein the agricultural composition further comprises an agricultural active compound B.

[0206] 44. The composition according to embodiment 40 or the agricultural composition according to any one of embodiments 38 to 39, wherein the composition or the agricultural composition comprises at least one of agricultural active compound A or agricultural active compound B, and each of agricultural active compound A and agricultural active compound B is independently an acaricide, an antimicrobial agent, a fungicide, a herbicide, an insecticide, a molluscicide or a nematicide or a combination thereof.

[0207] 45. The composition or agricultural composition as described in embodiment 44, wherein each of agricultural active compound A and agricultural active compound B is independently a fungicide.

[0208] 46. The composition or agricultural composition as described in embodiment 44, wherein each of agricultural active compound A and agricultural active compound B is independently 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, OSBPI fungicides, triazoleformamide fungicides, Group 27 fungicides, carbamate fungicides, benzamide fungicides, demethylation-inhibiting fungicides, piperazine fungicides, pyrimidine fungicides, imidazole fungicides, triazole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, QoI methacrylate fungicides, quinoline fungicides, inorganic fungicides, copper fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, guanidine fungicides, QiI fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0209] 47. The composition or agricultural composition as described in embodiment 44, wherein each of agricultural active compound A and agricultural active compound B is independently a fungicide selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluxapyroxad, flutolanil, fluopyram, indoxacarb, isofetamid, oxycarboxin, pencycuron, sedaxane, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, thiabendazole, cymoxanil, propamocarb, fluopicolide, zineb, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or a combination thereof.

[0210] 48. A method of using the agricultural composition as described in any one of embodiments 41 to 47, the method comprising applying the agricultural composition to a plant, a part of a plant, a seed, soil in which a plant is growing or will grow, or soil in which a seed has been or will be sown.

[0211] 49. A method for controlling or preventing fungal growth, the method comprising applying the agricultural composition as described in any one of embodiments 41 to 47 to a site where fungal growth has occurred or is at risk of occurring.

[0212] 50. A method for controlling or preventing fungal growth, the method comprising:

[0213] diluting the composition as described in any one of embodiments 1 to 40 or embodiments 44 to 47 with water and / or a lipophilic solvent to form a diluted mixture; and

[0214] applying the diluted mixture to a site where fungal growth has occurred or is at risk of occurring.

[0215] 51. The method according to embodiment 50, wherein the composition is the composition according to any one of embodiments 1 to 39, and diluting the composition further comprises adding an agroactive compound.

[0216] 52. The method according to embodiment 50, wherein adding the agroactive compound comprises adding an amount of the agroactive compound that is less than the amount of the agroactive compound recommended for use in the absence of the composition according to any one of embodiments 1 to 39.

[0217] 53. The method according to any one of embodiments 51 to 52, wherein the 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, OSBPI fungicides, triazoleformamide fungicides, group 27 fungicides, carbamate fungicides, benzamide fungicides, demethylation-inhibiting fungicides, piperazine fungicides, pyrimidine fungicides, imidazole fungicides, triazole fungicides, morpholine fungicides, group U6 fungicides, group 50 fungicides, QoI methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, guanidine fungicides, QiI fungicides, polyoxin fungicides, group 29 fungicides, thiazolidine fungicides, or combinations thereof.

[0218] 54. The method according to any one of embodiments 51 to 42, wherein the agroactive compound is a fungicide selected from: benomyl, thiabendazole, thiophanate-methyl, iprodione, vinclozolin, fludioxonil, cyprodinil, pyrimethanil, fenhexamid, amisulbrom, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, fluxapyroxad, solat enol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, chlorothalonil, cymoxanil, propamocarb, fluopicolide, zineb, mancozeb, maneb, metiram, ferbam, thiram, ziram, chloroneb (DCNA), chlorozolinate, quintozene, chlorothalonil, captan, dodine, cyazofamid, polyoxin, fluazinam, fluopyram or a combination thereof.

[0219] 55. Use of the agricultural composition according to any one of embodiments 41 to 47 for application to plants, parts of plants, seeds, soil in which plants are growing or are to grow, or soil in which seeds have been or are to be sown.

[0220] 56. Use of the agricultural composition according to any one of embodiments 41 to 47 for controlling or preventing fungal growth at sites where fungal growth is occurring or is at risk of occurring.

[0221] VII. Examples

[0222] Example 1

[0223] An oily flowable formulation was prepared as follows: 2 g of K30 (polyvinylpyrrolidone) was dissolved in 53 g of D80 paraffinic solvent. 5 g of a 50 rheology modifier and the mixture were subjected to high shear to activate the rheology modifier.

[0224] 40 g of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, which had been previously air-milled to have a median particle size below 2 microns, was dispersed into the mixture. The oily flowable formulation was expected to have excellent chemical and physical stability.

[0225] Example 2

[0226] Prepare an oily dispersible preparation as follows: Dissolve 2 g of Luvitec K30 in 46 g of Steposol TM ME (methyl oleate / linoleate). Add 5 g Gel 0434 rheology modifier together with 3 g of emulsifier LF700, 4 g ABS 60C-EH.

[0227] Disperse 40 g of (E)-3-methyl-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide, which has been previously air-milled to have a median particle size of less than 2 microns, into the mixture. The oily dispersible preparation is expected to have excellent chemical and physical stability.

[0228] Example 3

[0229] Chemical stability

[0230] Prepare samples according to the method described herein, such as in Example 1 above, except that low concentrations of certain components (including primary, secondary, tertiary, or quaternary amines) are added to specific sub-samples. Evaluate the chemical stability of the samples by storing the samples at high temperature and periodically measuring the remaining concentration of the active ingredient by HPLC. Store the reference samples at low temperature and also test them at the same time points. Certain components are expected to accelerate chemical degradation and must be excluded from the formulations of the present invention.

[0231] According to many possible embodiments in which the principles of the disclosed invention can be applied, it should be recognized that the illustrated embodiments are merely preferred examples of the present invention and should not be considered as limiting the scope of the present invention. On the contrary, the scope of the present invention is defined by the following claims. We therefore claim as our invention all that comes within the scope and spirit of these claims.

[0232] Appendix 1

[0233]

[0234]

[0235]

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[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256] Appendix 2

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269] Appendix 3

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[0271]

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[0280]

[0281]

Claims

1. A composition, the composition comprising: a compound having the following structure a lipophilic solvent; a first dispersant; and a rheology modifier.

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

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

4. The composition according to claim 3, wherein the volume weighted median particle size is from 0.1 micrometer to 5 micrometers.

5. The composition according to claim 1, wherein the volume weighted median particle size of the compound is less than about 15 micrometers as measured by light scattering.

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

7. The composition according to claim 3, wherein the volume weighted median particle size is from 0.5 micrometer to 2 micrometers.

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

9. The composition according to any one of claims 1 to 8, wherein the lipophilic solvent comprises mineral oil, fatty acid, vegetable oil or seed oil, terpene, aliphatic solvent, cycloaliphatic solvent, aromatic solvent or their derivatives and / or combinations.

10. The composition according to claim 9, wherein the lipophilic solvent comprises fatty acid derivatives.

11. The composition according to claim 10, wherein the fatty acid derivatives are selected from fatty acid esters, fatty acid dialkylamides and combinations thereof.

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

13. The composition according to claim 9, wherein the lipophilic solvent comprises paraffinic solvents.

14. The composition according to claim 9, wherein the lipophilic solvent comprises aromatic solvents.

15. The composition according to claim 9, wherein the lipophilic solvent comprises tetrahydronaphthalene, alkylated naphthalenes, their derivatives or combinations thereof.

16. The composition according to any one of claims 3 to 8, wherein the particles are present in an amount of 5 wt% to 90 wt%.

17. The composition according to any one of claims 3 to 8, wherein the particles are present in an amount of 30 wt% to 85 wt%.

18. The composition according to any one of claims 3 to 8, wherein the particles are present in an amount of 30 wt% to 50 wt%.

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

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

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

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

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

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

25. The composition according to any one of claims 1 to 23, wherein the first dispersant is a nonionic dispersant.

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

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

28. The composition according to claim 27, wherein the copolymer is a random or statistical copolymer, a block copolymer, a comb-shaped block copolymer, or a combination thereof.

29. The composition according to any one of claims 1 to 26, wherein the first 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 a combination thereof.

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

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

32. The composition according to any one of claims 1 to 31, the composition further comprising an emulsifier and a second dispersant.

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

34. The composition according to claim 32 or claim 33, wherein the emulsifier is an anionic surfactant, a cationic surfactant, a nonionic surfactant, a quaternary ammonium salt surfactant, an amphoteric surfactant, or a combination thereof.

35. The composition according to claim 34, wherein the emulsifier is selected from anionic surfactants, cationic surfactants, nonionic surfactants, or a combination thereof.

36. The composition according to claim 34 or claim 35, wherein: the anionic surfactant is a citrate ester, a carboxylate ester, a phosphate ester, a phosphonate ester, a sulfate ester, or a sulfonate ester of an alcohol, an alcohol ethoxylate, a triphenylvinylphenol ethoxylate, a fatty acid, or a natural oil, or any combination thereof; the cationic surfactant is an ethoxylated amine of a natural oil, an alcohol, a fatty acid, or a combination thereof; or The non-ionic surfactant is a polyethoxylated and / or polypropoxylated product of an alcohol, a natural oil, or a combination thereof.

37. The composition according to any one of claims 1 to 36, wherein the composition comprises no more than 0.1 wt% of a compound comprising a primary amine, a secondary amine, and / or a tertiary amine.

38. The composition according to any one of claims 1 to 37, wherein the composition comprises no more than 0.1 wt% of a quaternary ammonium compound.

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

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

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

42. The agricultural composition according to claim 41, wherein the agricultural composition comprises 0.01 wt% to 10 wt% of a composition according to any one of claims 1 to 40.

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

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

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

46. The composition or agricultural composition according to claim 44, wherein each of agricultural active compound A and agricultural active compound B is independently 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, OSBPI fungicides, triazoleformamide fungicides, Group 27 fungicides, carbamate fungicides, benzamide fungicides, demethylation-inhibiting fungicides, piperazine fungicides, pyrimidine fungicides, imidazole fungicides, triazole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, QoI methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper fungicides, sulfur fungicides, lime sulfur fungicides, ethylene bisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, guanidine fungicides, QiI fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

47. The composition or agricultural composition according to claim 44, wherein each of agricultural active compound A and agricultural active compound B is independently 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, trifloxystrobin, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, fluopyram, azoxystrobin, chlorothalonil, imazalil, triflumizole, cyproconazole, difenoconazole, fenbuconazole, flusilazole, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, fenpropidin, spiroxamine, cyflufenamid, metrafenone, picoxystrobin, oxathiapiprolin, fluazinam, fluthianil, cyazofamid, polyoxin, fluazinam, fluopyram, flutianil, fluthianil, or combinations thereof.

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

49. A method for controlling or preventing fungal growth, the method comprising applying an agricultural composition as described in any one of claims 41 to 47 to a site where fungal growth has occurred or is at risk of occurring.

50. A method for controlling or preventing fungal growth, the method comprising: diluting a composition as described in any one of claims 1 to 40 or claims 44 to 47 with water and / or a lipophilic solvent to form a diluted mixture; and applying the diluted mixture to a site where fungal growth has occurred or is at risk of occurring.

51. The method according to claim 50, wherein the composition is a composition as described in any one of claims 1 to 39, and diluting the composition further comprises adding an agroactive compound.

52. The method according to claim 50, wherein adding the agroactive compound comprises adding an amount of the agroactive compound that is less than the amount of the agroactive compound recommended for use in the absence of a composition as described in any one of claims 1 to 39.

53. The method according to any one of claims 51 to 52, wherein the 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, OSBPI fungicides, triazoleformamide fungicides, Group 27 fungicides, carbamate fungicides, benzamide fungicides, demethylation-inhibiting fungicides, piperazine fungicides, pyrimidine fungicides, imidazole fungicides, triazole fungicides, morpholine fungicides, Group U6 fungicides, Group 50 fungicides, QoI methoxyacrylate fungicides, quinoline fungicides, inorganic fungicides, copper fungicides, sulfur fungicides, lime sulfur fungicides, ethylenebisdithiocarbamate (EBDC) fungicides, EBDC-like fungicides, aromatic hydrocarbon fungicides, chloronitrile fungicides, phthalimide fungicides, guanidine fungicides, QiI fungicides, polyoxin fungicides, Group 29 fungicides, thiazolidine fungicides, or combinations thereof.

54. The method according to any one of claims 51 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, carboxin, fluxapyroxad, flutolanil, fluopyram, indoxacarb, isofetamid, oxycarboxin, pyraclostrobin, solatenol (benzovindiflupyr), metalaxyl-M, metalaxyl, oxadixyl, tribasic aluminum salts, phosphoric acid, dimethomorph, mandipropamid, flutianiliprole, thifluzamide, cymoxanil, propamocarb, fluopicolide, azoxystrobin, chlorothalonil, imazalil, triflumizole, cyproconazole, difenoconazole, myclobutanil, florylpicoxamid, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, fenarimol, spiroxamine, cyflufenamid, metrafenone, picoxystrobin, oxathiapiprolin, fluoxastrobin, pyraoxystrobin, coumethoxystrobin, pyribencarb, kresoxim-methyl, trifloxystrobin, 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.

55. Use of an agricultural composition according to any one of claims 41 to 47 for application to plants, parts of plants, seeds, soil in which plants are growing or are to grow, or soil in which seeds have been or are to be sown.

56. Use of an agricultural composition according to any one of claims 41 to 47 for controlling or preventing fungal growth at sites where fungal growth is occurring or at risk of occurring.

Images