OA20987A - A difluoro-(2-HydroxypropyI) pyridine compound as a fungicide for black Sigatoka. - Google Patents

Abstract

The present disclosure is related to the field of agrochemicals, specifically the resent disclosure provides for fungicidal compound I and its' use to control diseases in plants of the Musa genus.

Description

A DIFLUORO-(2-HYDROXYPROPYL)PYRIDINE COMPOUND AS A FUNGICIDE FOR BLACK SIGATOKA

1. CROSS-REFERENCE TO RELATED APPLICATIONS

The présent application daims priority to U.S. Provisional Patent Application Ser. No. 62/814631 filed March 6, 2019, the disclosure of which is hereby incorporated by reference in its entirety.

2. BACKGROUND

Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage caused by agriculturally-relevant fongi. Generally, no single fongicide is usefol in ail situations. In particular Mycosphaerella fljiensis fungi are problematic on crops such as bananas. Consequently, research is ongoing to produce fungicidal compounds that may hâve better performance, are easier to use, and cost less.

3. SUMMARY

Compound I is known as an existing fungicidal compound. The structure of Compound is:

Compound I is also known by its Chemical name: 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro2-hydroxy-3-(5-thioxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)propyl)pyridin-3-yl)oxy)benzonitrile.

The synthesis of Compound I is described in U.S. Patent Application No. 15/574,775, which is hereby incorporated by reference in its entirety.

Black sigatoka disease is one of the most destructive diseases on worldwide in banana crops. Almost ail banana leaf parts are affected by this pathogen. As a new triazole in this market, Compound I provides a very important tool for controlling this disease in banana.

In general, the présent disclosure relates to Compound I and its use as a fongicide for plants in the genus Musa. It is found that Compound I is particularly active against Mycosphaerella fijiensis fongi. Specifically Compound I offers superior protection against this fongal pathogen, which causes black leaf streak disease (BLSD) or black Sigatoka. However, Compound I also has activity against other fungi and other diseases of plants.

In one aspect, the présent disclosure provides a method of controlling or preventing pathogen-induced disease in a plant in the genus Musa. Such plants are at risk of being diseased from, for example, Mycosphaerella fijiensis pathogen. In some such aspects, the disclosure herein provides a method of controlling or preventing black Sigatoka or black leaf streak disease (BLSD) in a plant, the method comprising treating the plant or area adjacent to the plant with Compound I, or a composition including Compound I.

In some aspects, the présent disclosure provides methods of controlling or eradicating Mycosphaerella fijiensis pathogen. In such aspects, progression of the disease may or may not be arrested, however the pathogen is removed. Moreover in such aspects, Compound I has specificity against Mycosphaerella fijiensis. That is to mean that Compound I has activity especially against this pathogen, but may also hâve lesser efficacy or efficiency against other pathogens. For example Compound I may almost total kill ail Mycosphaerella fijiensis fungi présent, however at the same time (or in or on the same plant) may only kill 10, 20, 30, 40, 50, 60, 70, 75, 80, 85, or 90% of other fungi - for example fungi such as Colletotrichum cereale and/or Verticillium clahliae. Accordingly, Compound I is sélective for Mycosphaerella fijiensis.

In some aspects, the présent disclosure provides methods of controlling or eradicating other biologically relevant fungi in plants in the genus Musa, such fungi include M. musicola, Helminthosporium torulosum and/or Pestalotia leprogena.

In some aspects, the présent disclosure provides for methods or for uses of Compound I for protection of a plant against attack by the phytopathogenic organism, or the treatment of a plant infested by a phytopathogenic organism, Mycosphaerella fijiensis, the method or use comprising the application of Compound I, or a composition including Compound I to soil, a plant, a part of a plant, foliage, and/or seeds.

In some aspects, the présent disclosure provides for methods of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising the method comprising treating the plant or area adjacent to the plant with Compound I, or a composition including Compound I. In some of these aspects, the disease is black Sigatoka. In some of these aspects, the disease is black Sigatoka. In some of these aspects, the disease is Tropical race 4 (TR4).

In some aspects, the présent disclosure provides for a composition useful for protecting a plant against attack by a Mycosphaerella fiijiensis and/or treatment of a plant infested by a Mycosphaerella fijiensis comprising a phytologically acceptable amount of Compound I and a carrier material. In such aspects, the components of and the manufacture of the composition is well known in the art as phytological or fungicide compositions, and the carriers used therefor, are exhaustively described in many primary references, and including those which are disclosed herein.

In some aspects, the présent disclosure provides for a compositions comprising Compound I and an active. In such aspects, the active is an agriculturally active ingrédient. Agriculturally active ingrédients include, but certainly are not limited to, existing or known insecticides, herbicides, and fungicides.

4. DETAILED DESCRIPTION

4.1. Définitions

Varions terms used in the spécification and daims herein are defïned as set forth below, unless otherwise specifically defïned in this disclosure. Ail technical and scientific terms not defïned herein hâve the meaning commonly understood by a person skilled in the art to which this invention belongs.

As used herein, the term sait refers to salts which are suitable for use in agriculture, i.e. they affect humans and lower animais without undue toxicity, irritation, allergie response and the like, and are commensurate with a reasonable benefit/risk ratio in agriculture. These salts are well known in the art. Salts of the compounds described herein include those derived from suitable inorganic and organic acids and bases. Examples of acid addition salts are salts of an amino group formed with inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid and perchloric acid or with organic acids such as acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid or malonic acid or by using other methods used in the art such as ion exchange. Other salts include, but are not limited to, adipate, alginate, ascorbate, aspartate, benzenesulfonate, benzoate, bisulfate, borate, butyrate, camphorate, camphorsulfonate, citrate, cyclopentanepropionate, digluconate, dodecyl sulfate, ethanesulfonate, formate, fumarate, glucoheptonate, glycérophosphate, gluconate, hemisulfate, heptanoate, hexanoate, hydroiodide, 2hydroxy-ethanesulfonate, lactobionate, lactate, laurate, lauryl sulfate, malate, maleate, malonate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, oleate, oxalate, palmitate, pamoate, pectinate, persulfate, 3-phenylpropionate, phosphate, pivalate, propionate, stéarate, succinate, sulfate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate salts, and the like. Salts derived from appropriate bases include alkali métal, alkaline earth métal, ammonium salts. Représentative alkali or alkaline earth métal salts include sodium, lithium, potassium, calcium, magnésium, and the like. Further pharmaceutically acceptable salts include, when appropriate, nontoxic ammonium, quatemary ammonium, and amine cations formed using counterions such as halide, hydroxide, carboxylate, sulfate, phosphate, nitrate, loweralkyl sulfonate and aryl sulfonate.

“Tautomer” refers to altemate forms of a compound that differ in the position of a proton, such as enol-keto and imine-enamine tautomers, or the tautomeric forms of heteroaryl groups containing a ring atom attached to both a ring NH moiety and a ring =N moiety such as pyrazoles, imidazoles, benzimidazoles, triazoles, and tetrazoles.

Phytologically acceptable amount refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, climate conditions, and the like. A suitabîe application rate is typically in the range from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m²).

The term disease-inhibiting and phytologically acceptable amount refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, climate conditions, and the like. A suitabîe application rate is typically in the range from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m²).

4.2. Additional interpretational conventions

Generally, référencé to or depiction of a certain element such as hydrogen or H is meant to include ail isotopes of that element. For example, if an R group is defined to include hydrogen or H, it also includes deuterium and tritium. Compounds comprising radioisotopes such as tritium, C, P and S are thus within the scope of the présent technology. Procedures for inserting such labels into the compounds of the présent technology will be readily apparent to those skilled in the art based on the disclosure herein.

Unless the spécifie stereochemistry is expressly indicated, ail chiral, diastereomeric, and racemic forms of a compound are intended. Thus, compounds described herein include enriched or resolved optical isomers at any or ail asymmetric atoms as are apparent from the depictions. Racemic mixtures, and d or 1 enriched stereomeric mixtures, as well as the individual optical isomers can be isolated or synthesized so as to be substantially free of their enantiomeric or diastereomeric partners, and these stereoisomers are ail within the scope of the présent technology.

The compounds described herein may exist as solvatés, especially hydrates, and unless otherwise specified, ail such solvatés and hydrates are intended. Hydrates may form during manufacture of the compounds or compositions comprising the compounds, or hydrates may form over time due to the hygroscopic nature of the compounds. Compounds of the présent technology may exist as organic solvatés as well, including DMF, ether, and alcohol solvatés, among others. The identification and préparation of any particular solvaté is within the skill of the ordinary artisan of synthetic organic or médicinal chemistry.

Throughout this application, the text refers to varions embodiments of the présent compounds, compositions, and methods. The various embodiments described are meant to provide a variety of illustrative examples and should not be construed as descriptions of alternative species. Rather, it should be noted that the descriptions of various embodiments provided herein may be of overlapping scope. The embodiments discussed herein are merely illustrative and are not meant to limit the scope of the présent technology.

For the purposes of this spécification and appended daims, unless otherwise indicated, ail numbers expressing amounts, sizes, dimensions, proportions, shapes, formulations, parameters, percentages, parameters, quantifies, characteristics, and other numerical values used in the spécification and daims, are to be understood as being modified in ail instances by the term “about” even though the term “about” may not expressly appear with the value, amount or range. Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following spécification and attached daims are not and need not be exact, but may be approximate and/or larger or smaller as desired, reflecting tolérances, conversion factors, rounding off, measurement error and the like, and other factors known to those of skill in the art depending on the desired properties sought to be obtained by the presently disclosed subject matter. For example, the term “about,” when referring to a value can be meant to encompass variations of, in some aspects, ± 100% in some aspects ± 50%, in some aspects ± 20%, in some aspects ± 10%, in some aspects ± 5%, in some aspects ±1%, in some aspects ± 0.5%, and in some aspects ± 0.1% from the specified amount, as such variations are appropriate to perform the disclosed methods or employ the disclosed compositions.

As used herein and in the appended daims, singular articles such as “a,” “an” and “the” and similar referents in the context of describing the éléments (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, including the upper and lower bounds of the range, unless otherwise indicated herein, and each separate value is incorporated into the spécification as if it were individually recited herein. Ail methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and ail examples, or exemplary language (e.g. “such as”) provided herein, is intended merely to better illuminate the embodiments and does not pose a limitation on the scope of the claims unless otherwise stated. No language in the spécification should be construed as indicating any non-claimed element as essential.

4.3. Methods of control or prévention 4.3.1. Disease

In some aspects, the présent disclosure provides for methods of controlling or preventing disease in a plant in the genus Musa. In some aspects, the présent disclosure provides for methods of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising treating the plant or area adjacent to the plant with Compound I, or a tautomer or sait thereof, or a composition including Compound I.

In some aspects, the présent disclosure provides for a method of controlling or preventing fungal disease in a plant in the genus Musa,, the method comprising contacting the plant or area adjacent to the plant with Compound I:

Compound I , or a tautomer or sait thereof.

In some aspects, the présent disclosure provides for a method of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, wherein Compound I is according to the structure:

Compound I

In some aspects, the présent disclosure provides for a method of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

Compound I , or a tautomer or sait thereof, or a composition

Compound I

In some aspects, the présent disclosure provides for a method of controlling or preventing black Sigatoka in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

Compound I , or a tautomer or sait thereof, or a composition

Compound I

In some aspects, the présent disclosure provides for a method of controlling or preventing black Sigatoka in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

or the plant, with Compound I

Compound I , or a tautomer or sait thereof, or a composition

Compound I

In some aspects, the présent disclosure provides for a method of controlling or preventing Banana bacterial wilt (BBW) in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root ofthe

Compound I or plant, and/or foliage of the plant, with

Compound I , or a tautomer or sait thereof, or a composition

Compound I or comprising

Compound I

In some of these aspects, the disease is black Sigatoka. In some of these aspects, the disease is Banana bacterial wilt (BBW). In some aspects, the disease is Tropical race 4 (TR4). In some aspects, the disease is Banana bunchy top virus (BBTV).

In some aspects, the présent disclosure provides for methods wherein Compound I is

according to the structure: Compound I i_{n some aspects}, _the présent disclosure provides for methods wherein Compound I is according to the structure:

Compound I

4.3.2. Fungi

In some aspects, the présent disclosure provides for methods of controlling or preventing attack of the fungal pathogen, Mycosphaerella fijiensis.

In some aspects, the présent disclosure provides for a method of controlling or eradicating Mycosphaerella fijiensis fungal pathogen in a plant, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, wherein Compound I is according to the structure:

Compound I

In some aspects, the présent disclosure provides for a method controlling or eradicating Mycosphaerella fijiensis fungal pathogen in a plant, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or

Compound I , or a tautomer or sait thereof, or a composition

Compound I or comprising

Compound I

In some aspects, the présent disclosure provides for a method of controlling or eradicating Mycosphaerellafîjiensis fungal pathogen in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a

Compound I root of the plant, and/or foliage of the plant, with

Compound I , or a tautomer or sait thereof, or a composition

Compound I

In some aspects, the présent disclosure provides for methods of controlling or eradicating one or more of M. musicola, Helminthosporium torulosum and/or Pestalotia leprogena pathogen in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a fungicide composition comprising a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, and a carrier, wherein Compound I is according to the structure:

Compound I

In some aspects, the présent disclosure provides for methods of controlling or eradicating one or more of M. musicola, Helminthosporium torulosum and/or Pestalotia leprogena pathogen in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a fungicide composition comprising a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, and a carrier, wherein Compound I is according to the structure:

Compound I

Compound I tautomer or sait thereof.

In some aspects, the pathogen is M. musicola. In some aspects, the pathogen is Helminthosporium torulosum. In some aspects, the pathogen is Pestalotia leprogena.

A method of controlling or preventing fungal disease in a plant in the genus Musa, or controlling or eradicating Mycosphaerella fijiensis fungal pathogen in a plant, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a fungicide composition comprising a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, and a carrier, wherein Compound I is according to the structure:

Compound I

4.3.3. Compositions

In some aspects, the présent disclosure provides for methods wherein the composition further comprises an agriculturally active ingrédient selected from the group consisting of: insecticide, an herbicide, and a fungicide.

Insecticides, herbicides, and fungicides are well known in the art and described further herein.

In some aspects, the présent disclosure provides for methods wherein the composition carrier includes one or more of a thickener, emulsifier, rheology agent, dispersant and/or solid carrier.

In varions aspects, Compound I is applied by any of a variety of known techniques, either as Compound I or as formulations comprising Compound I. For example, Compound I may be applied to the roots, seeds, stems, flowers, or foliage of plants for the control of varions fongi, without damaging the commercial value of the plants. Compound I may also be applied as a foliar spray, soil drench, soil injection, seed treatment or water application in aquaculture and floating nursery trays. The material may be applied in the form of any of the generally used formulation types, for example, as solutions, dusts, wettable powders, flowable concentrâtes, or emulsifiable concentrâtes.

Preferably, Compound I of the présent disclosure is applied in the form of a formulation that includes Compound I with a phytologically acceptable carrier. Concentrated formulations may be dispersed in water or other liquids for application, or formulations may be dust-like or granular, which may then be applied without further treatment. The formulations can be prepared according to procedures that are conventional in the agricultural Chemical art.

The présent disclosure contemplâtes ail carrier or vehicles by which Compound I may be formulated for delivery and use as a fongicide. That is, the formulations that are disclosed, contemplated and will work ail with formula I include ail the carriers that one skilled in the art would use for agricultural fongicide formulations. Typically, formulations are applied as aqueous suspensions or émulsions. Such suspensions or émulsions may be produced from water-soluble, water-suspendible, or emulsifiable formulations which are solids, usually known as wettable powders; or liquids, usually known as emulsifiable concentrâtes, aqueous suspensions, or suspension concentrâtes. As will be readily appreciated, any material to which Compound I may be added may be used, provided it yields the desired utility without significant interférence with the activity of Compound I as an antifungal agent.

Wettable powders, which may be compacted to form water-dispersible granules, comprise an intimate mixture including Compound I, an inert carrier and surfactants. The concentration of Compound I in the wettable powder may be from about 10 percent to about 90 percent by weight based on the total weight of the wettable powder, more preferably about 25 weight percent to about 75 weight percent. In the préparation of wettable powder formulations, Compound I may be compounded with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates or the like. In such operations, the finely divided carrier and surfactants are typically blended with Compound I and milled.

Emulsifiable concentrâtes of Compound I may comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of Compound I, in a suitable liquid, based on the total weight of the concentrate. Compound I may be dissolved in an inert carrier, which is either a water-miscible solvent or a mixture of water-immiscible organic solvents, and emulsifiers. The concentrâtes may be diluted with water and oil to form spray mixtures in the form of oil-in-water émulsions. Useful organic solvents include aromatics, especially the highboiling naphthalenic and olefmic portions of petroleum, such as heavy aromatic naphtha. Other organic solvents may also be used, for example, terpenic solvents, including rosin dérivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.

Emulsifiers which may be advantageously employed herein may be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrâtes include the polyalkylene glycol ethers and condensation products of alkyl and aryl phénols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phénols and carboxylic esters solubilized with the polyol or polyoxyalkylene. Cationic emulsifiers include quatemary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts of phosphated polyglycol ether.

Représentative organic liquids which may be employed in preparing the emulsifiable concentrâtes of Compound I of the présent invention are the aromatic liquids such as xylene, propyl benzene fractions; or mixed naphthalene fractions, minerai oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol dérivatives such as the «-butyl ether, ethyl ether or methyl ether of diethylene glycol, and the methyl ether of triethylene glycol and the like. Mixtures of two or more organic liquids may also be employed in the préparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with Compound I. The formulations can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture.

Aqueous suspensions including Compound I may be dispersed in an aqueous vehicle at a concentration in the range from about 5 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding Compound I, and vigorously mixing the ground material into a vehicle comprised of water and surfactants chosen from the same types discussed above. Other components, such as inorganic salts and synthetic or natural gums, may also be added to increase the density and viscosity of the aqueous vehicle.

Compound I may also be applied as a granular formulation, which is particularly useful for applications to the soil. Granular formulations generally contain from about 0.5 to about 10 weight percent, based on the total weight of the granular formulation of Compound I, dispersed in an inert carrier which consists entirely or in large part of coarsely divided inert material such as attapulgite, bentonite, diatomite, clay or a similar inexpensive substance. Such formulations are usually prepared by dissolving Compound I in a suitable solvent and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to about 3 mm. A suitable solvent is a solvent in which Compound I is substantially or completely soluble. Such formulations may also be prepared by making a dough or paste of the carrier and Compound I and solvent, and crushing and drying to obtain the desired granular particle.

Dusts containing Compound I may be prepared by intimately mixing Compound I in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of Compound I, based on the total weight of the dust.

The formulations may additionally contain adjuvant surfactants to enhance déposition, wetting and pénétration of Compound I onto the target crop and organism. These adjuvant surfactants may optionally be employed as a component of the formulation or as a tank mix. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a spray-volume of water, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phénols, ethoxylated synthetic or natural alcohols, salts of the esters or sulphosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with minerai or vegetable oils. The formulations may also include oil-in-water émulsions such as those disclosed in U.S. Patent Application Serial No. 11/495,228, the disclosure of which is expressly incorporated by reference herein.

In certain instances, it would be bénéficiai for formulations of the current composition to be sprayed via an aerial application using aircraft or helicopters. The exact components of these aerial applications dépends upon the crop being treated. Aerial applications for cereals utilize spray volumes preferably from 15 to 25 L/ha with standard spreading or penetrating type adjuvants such as non-ionic surfactants or crop oil concentrâtes, preferably from 0.05 to 15 percent, based on a spray volume of water. Aerial applications for fruit bearing crops, such as bananas, may utilize lower application volumes with higher adjuvant concentrations, preferably in the form of sticker adjuvants, such as fatty acids, latex, aliphatic alcohols, crop oils and inorganic oils. Typical spray volumes for fruit bearing crops are preferably from 15 to 30 L/ha with adjuvant concentrations reaching up to 30% based on a spray volume of water. A typical example might include, but not limited to, an application volume of 23 L/ha, with a 30% paraffm oil sticker adjuvant concentration (e.g. Spraytex CT).

Methods to make and use these agricultural compositions comprising the Compound I may be found in, for example, référencés such as, Hance et al. Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001, Perry's Chemical Engineer's Handbook, 4th Ed., McGrawHill, New York, 1963, Browning, et al. Agglomération in Chemical Engineering, Dec. 4, 1967, 147- 48, Klingman, Weed Control as a Science (J. Wiley & Sons, New York, 1961) and US 3,060,084, US 3,299,566, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, EP 707 445, GB 2,095,558, and WO9113546, each of which is incorporated by reference in its entirety.

Each one of the methods disclosed herein are contemplated to use any of the formulations described herein, and said formulations may optionally include combinations that contain other pesticidal compounds. Such additional pesticidal compounds may be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactéricides or combinations thereof that are compatible with the compounds of the présent invention in the medium selected for application, and not antagonistic to the activity of the présent compounds. Accordingly, in such embodiments, the other pesticidal Compound Is employed as a supplémentai toxicant for the same or for a different pesticidal use. Compound I and the pesticidal Compound In the combination can generally be présent in a weight ratio of from 1:100 to 100:1.

Compound I of the présent disclosure may also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. Compound I of the présent disclosure is often applied in conjunction with one or more other fungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), the presently claimed Compound I may be formulated with the other fungicide(s), tank-mixed with the other fungicide(s) or applied sequentially with the other fungicide(s). Such other fungicides may include 2(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis,

Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) sait, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluindapyr, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldéhyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acétates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)-2(methoxymethyl)-succinimide, 1,2-dichloropropane, l,3-dichloro-l,l,3,3-tetrafluoroacetone hydrate, l-chloro-2,4-dinitronaphthalene, l-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-lyl)ethanol, 2,3-dihydro-5-phenyl-l,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5methylrhodanine, 4-(2-nitroprop-l-enyl)phenyl thiocyanateme, ampropylfos, anilazine, azithiram, barium polysulfïde, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril; benzamacrilisobutyl, benzamorf, benzovindiflupyr, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3phenylsalicylate), copper zinc chromate, coumoxystrobin, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlobentiazox, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipymetitrone, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, enoxastrobin, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenaminstrobin, fenapanil, fenitropan, fenpicoxamid, fluotrimazole, flufenoxystrobin, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, ipfentrifluconazole, isofetamid, isopamphos, isovaledione, mandestrobin, mebenil, mecarbinzid, mefentrifluconazole, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, A-3,5-dichlorophenyl-succinimide, A-3-nitrophenylitaconimide, natamycin, Nethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, oxathiapiprolin, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb;

prothiocarb hydrochloride, pydiflumetofen, pyracarbolid, pyraziflumid, pyridinitril, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol, quinacetol sulfate, quinazamid, quinconazole, quinofumelin, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, triclopyricarb, triflumezopyrim, urbacid, zarilamid, and any combinations thereof.

Additionally, Compound I of the présent invention may be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactéricides or combinations thereof that are compatible with Compound I of the présent invention in the medium selected for application, and not antagonistic to the activity of Compound I, to form pesticidal mixtures and synergistic mixtures thereof. Compound I of the présent disclosure may be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests. When used in conjunction with other pesticides, the presently claimed Compound I may be formulated with the other pesticide(s), tank mixed with the other pesticide(s) or applied sequentially with the other pesticide(s). Typical insecticides include, but are not limited to: 1,2-dichloropropane, abamectin, acephate, acetamiprid, acethion, acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, allyxycarb, alpha-cypermethrin, alpha-ecdysone, alpha-endosulfan, amidithion, aminocarb, amiton, amiton oxalate, amitraz, anabasine, athidathion, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azothoate, barium hexafluorosilicate, barthrin, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, beta-cypermethrin, bifenthrin, bioallethrin, bioethanomethrin, biopermethrin, bistrifluron, borax, boric acid, bromfenvinfos, bromocyclen, bromo-DDT, bromophos, bromophos-ethyl, bufencarb, buprofezin, butacarb, butathiofos, butocarboxim, butonate, butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide, camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, cartap, cartap hydrochloride, chlorantraniliprole, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform hydrochloride, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroform, chloropicrin, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I, cinerin II, cinerins, cismethrin, cloethocarb, closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate, coumaphos, coumithoate, crotamiton, crotoxyphos, crufomate, cryolite, cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyclethrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, cythioate, DDT, decarbofuran, deltamethrin, demephion, demephion-O, demephion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos, diatomaceous earth, diazinon, dicapthon, dichlofenthion, dichlorvos, dicresyl, dicrotophos, dicyclanil, dieldrin, diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate, dimethrin, dimethylvinphos, dimetilan, dinex, dinex-diclexine, dinoprop, dinosam, dinotefuran, diofenolan, dioxabenzofos, dioxacarb, dioxathion, disulfoton, dithicrofos, d-limonene, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, doramectin, ecdysterone, emamectin, emamectin benzoate, EMPC, empenthrin, endosulfan, endothion, endrin, EPN, epofenonane, eprinomectin, esdepalléthrine, esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, ethoate-methyl, ethoprophos, ethyl formate, ethyl-DDD, ethylene dibromide, ethylene dichloride, ethylene oxide, etofenprox, etrimfos, EXD, famphur, fenamiphos, fenazaflor, fenchlorphos, fenethacarb, feniluthrin, fenitrothion, fenobucarb, fenoxacrim, fenoxycarb, fenpirithrin, fenpropathrin, fensulfothion, fenthion, fenthion-ethyl, fenvalerate, fipronil, flonicamid, flubendiamide, flucofuron, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, fluvalinate, fonofos, formetanate, formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosmethilan, fospirate, fosthietan, fùrathiocarb, furethrin, gammacyhalothrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD, heptachlor, heptenophos, heterophos, hexaflumuron, HHDN, hydramethylnon, hydrogen cyanide, hydroprene, hyquincarb, imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isazofos, isobenzan, isocarbophos, isodrin, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane, isothioate, isoxathion, ivermectin, jasmolin I, jasmolin II, jodfenphos, juvénile hormone I, juvénile hormone II, juvénile hormone III, kelevan, kinoprene, lambda-cyhalothrin, lead arsenate, lepimectin, leptophos, lindane, lirimfos, lufenuron, lythidathion, malathion, malonoben, mazidox, mecarbam, mecarphon, menazon, mephosfolan, mercurous chloride, mesulfenfos, metaflumizone, methacrifos, methamidophos, methidathion, methiocarb, methocrotophos, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, methyl isothiocyanate, methylchloroform, methylene chloride, metofluthrin, metolcarb, metoxadiazone, mevinphos, mexacarbate, milbemectin, milbemycin oxime, mipafox, mirex, molosultap, monocrotophos, monomehypo, monosultap, morphothion, moxidectin, naftalofos, naled, naphthalene, nicotine, nifluridide, nitenpyram, nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeprofos, oxydisulfoton, paradichlorobenzene, parathion, parathion-methyl, penfluron, pentachlorophenol, permethrin, phenkapton, phenothrin, phenthoate, phorate, phosalone, phosfolan, phosmet, phosnichlor, phosphamidon, phosphine, phoxim, phoxim-methyl, pirimetaphos, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, primidophos, profenofos, profluralin, promacyl, promecarb, propaphos, propetamphos, propoxur, prothidathion, prothiofos, prothoate, protrifenbute, pyraclofos, pyrafluprole, pyrazophos, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins, pyridaben, pyridalyl, pyridaphenthion, pyrifluquinazon, pyrimidifen, pyrimitate, pyriprole, pyriproxyfen, quassia, quinalphos, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, ryania, sabadilla, schradan, selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad, spiromesifen, spirotetramat, sulcofuron, sulcofuron-sodium, sulfluramid, sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, tau-fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, theta-cypermethrin, thiacloprid, thiamethoxam, thicrofos, thiocarboxime, thiocyclam, thiocyclam oxalate, thiodicarb, thiofanox, thiometon, thiosultap, thiosultap-disodium, thiosultap-monosodium, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, triarathene, triazamate, triazophos, trichlorfon, trichlormetaphos-3, trichloronat, trifenofos, triflumuron, trimethacarb, triprene, vamidothion, vaniliprole, XMC, xylylcarb, zetacypermethrin, zolaprofos, and any combinations thereof.

Additionally, Compound I of the présent invention may be combined with herbicides that are compatible with Compound I of the présent invention in the medium selected for application, and not antagonistic to the activity of Compound I to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal Compound I of the présent disclosure may be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants. When used in conjunction with herbicides, the presently claimed Compound I may be formulated with the herbicide(s), tank mixed with the herbicide(s) or applied sequentially with the herbicide(s). Typical herbicides include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4-DB; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chloiprocarb, carfentrazone, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMP A, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flampropM, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glufosinate-P, glyphosate, halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, ΜΑΜΑ, MCP A, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ort/zo-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P, rhodethanil, rimsulfùron, saflufenacil, Smetolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vemolate, and xylachlor.

Some embodiments of the présent disclosure provide a method for the control or prévention of fungal attack. This method comprises applying to the soil, plant, roots, foliage, seed or locus of the fungus, or to a locus in which the infestation is to be prevented, a fungicidal effective amount of Compound I. Compound I is suitable for treatment of Musa plants at fungicidal levels, while exhibiting low phytotoxicity. Compound I may be useful both in a protectant and/or an eradicant fashion. It will be understood by those in the art that the efficacy of the compound for the foregoing fungi establishes the general utility of Compound I as a fungicide. In particular, the composition is effective in controlling a variety of undesirable fungi that infect banana plant crops. However, Compound I has a broad range of efficacy as a fungicide. Accordingly, Compound I or a composition of Compound I may be used, in any method described herein, against a variety of fungi (but may or may not be selectively active against Mycosphaerella fijiensis in the presence of any one of these other fungi), including but certainly not limited to the following fungi species: Anthracnose/fungal scald/crown rot/stem end rot (Colletotrichum musae), brown spot {Cercospora hayi), Cladosporium speckle (Cladosporium musaé), crown rot (Fusarium sp., Verticillium spp., Acremonium spp.), diamond spot (Cercospora hayi, Fiisarium spp.), Sclerotinia fruit rot {Sclerotinia sclerotiorum), Septoria leaf spot {Mycosphaerella eumiisae), yellow sigatoka {Mycosphaerella musicola), Sheath rot {Nectria foliicola, Mycosphaerella musicola), pitting {Pyricularia grisea), leaf spots and blotches {Drechslera gigantea, Curvularia eragrostidis, Drechslera musae-sapientnm, Leptosphaeria musarum, Pestalotiopsis clisseminata, Haplobasidion musae, Pestalotiopsis palmarum, Phaeoseptoria musae, Cordana johnstonii, Cordana musae, Pestalotiopsis leprogena), Panama disease {Fusarium oxysporum f.sp. cubense), sooty mold {Limacinula tennis'), root rots {Rosellinia bunodes, Fusarium solani, Fusarium oxysporum, Cylindrocladium spp., Rhizoctonia spp.), rots {Armillaria spp., Ceratocystisparadoxa, Junghuhnia vincta, Nattrassia mangiferae, Botryosphaeria ribis, Ceratocystis paradoxa, Marasmiellus inoderma, Lasiodiplodia theobromae, Fusarium spp., Verticillium spp, Cylindrocarpon musae, Trachysphaera fructigena, Deightoniella torulosa), speckles and freckles {Deightoniella torulosa, Guignarclia musae, Acrodontium simplex, Ramichloridium musae, Mycosphaerella musae), rusts {Uredo musae, Uromyces musae),

Compound I has a broad range of efficacy as a fungicide. The exact amount of the active material to be applied is dépendent not only on the spécifie active material being applied, but also on the particular action desired, the fungal species to be controlled, and the stage of growth thereof, as well as the part of the plant or other product to be contacted with the compound. Thus, Compound I, and formulations containing the same, may not be equally effective at similar concentrations or against the same fungal species.

Compound I is effective in use with plants in a disease-inhibiting and phytologically acceptable amount.

4.3.4. Rates

In some aspects, the présent disclosure provides for methods of controlling or preventing disease in a plant, wherein the rate of application of Compound I, or a composition including Compound I, is from 1-400 g ai/ha, 1-250 g ai/ha, 20-250 g ai/ha, 50-250 g ai/ha, 75-250 g ai/ha, 100-250 g ai/ha, 150-250 g ai/ha, or 200-250 g ai/ha.

In some aspects, the rate is from 25-250 g ai/ha. In some aspects, the rate is 1 g ai/ha, 2 g ai/ha, 3 g ai/ha, 4 g ai/ha, 5 g ai/ha, 6 g ai/ha, 7 g ai/ha, 8 g ai/ha, 9 g ai/ha, 10 g ai/ha, 15 g ai/ha, 20 g ai/ha, 25 g ai/ha, 30 g ai/ha, 35 g ai/ha, 40 g ai/ha, 45 g ai/ha, 50 g ai/ha, 55 g ai/ha, 60 g ai/ha, 65 g ai/ha, 70 g ahha, 75 g ai/ha, 80 g ai/ha, 85 g ai/ha, 90 g ai/ha, 95 g ai/ha, 100 g ai/ha, 105 g ai/ha, 110 g ai/ha, 115 g ai/ha, 120 g ai/ha, 125 g ai/ha, 130 g ai/ha, 135 g ai/ha, 140 g ai/ha, 145 g ai/ha, 150 g ai/ha, 155 g ai/ha, 160 g ai/ha, 165 g ai/ha, 170 g ai/ha, 175 g ai/ha, 180 g ai/ha, 185 g ai/ha, 190 g ai/ha, 195 g ai/ha, 200 g ai/ha, 205 g ai/ha, 210 g ai/ha, 215 g ai/ha, 220 g ai/ha, 225 g ai/ha, 230 g ai/ha, 235 g ai/ha, 240 g ai/ha, 245 g ai/ha, or 250 g ai/ha. In some aspects, the rate is 10 g ai/ha. In some aspects, the rate is 100 g ai/ha. In some aspects, the rate is 125 g ai/ha. In some aspects, the rate is 150 g ai/ha. In some aspects, the rate is 175 g ai/ha. In some aspects, the rate is 250 g ai/ha.

In some aspects, the présent disclosure provides for a method of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

the plant, with Compound I

comprising

Compound I or

Compound I

In some aspects, the présent disclosure provides for a method of controlling or preventing black Sigatoka in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

comprising

Compound I or

In some aspects, the présent disclosure provides for a method of controlling or preventing black Sigatoka in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of

comprising

Compound I or

In some aspects, the présent disclosure provides for a method of controlling or preventing Banana bacterial wilt (BBW) in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the

Compound I comprising or

4.3.5. Harvest

In some aspects, the présent disclosure provides for methods wherein the plant species is Musa acuminata or Musa balbisiana.

In some aspects, the présent disclosure provides for methods wherein the plant species is Musa acuminate.

In some aspects, the présent disclosure provides for methods wherein the plant species is Musa balbisiana.

In some aspects, the plant in the genus Musa has a fruit.

In some aspects, the présent disclosure provides for methods wherein the plant in the genus Musa has a fruit and the plant species is Musa acuminata or Musa balbisiana.

In some aspects, the présent disclosure provides for methods wherein the plant in the genus Musa has a fruit and the plant species is Musa acuminata.

In some aspects, the présent disclosure provides for methods wherein the plant in the genus Musa has a fruit and the plant species is Musa balbisiana.

In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerellafijiensis fungal pathogen reduces fruit yield from 2-95%, 5-95%, 10-95%, 20-95%, 30-95%, 40-95%, 50-95%, 60-95%, 70-95%, 80-95%, or 90-95% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield from 95-98% by weight.

In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 20%, 25%, 30%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, or 99% by weight.

In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 5% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 25% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 33% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 40% by weight.

In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 50% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 66% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 75% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 80% by weight. In some aspects, the présent disclosure provides for methods wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 90% by weight.

In some aspects, the présent disclosure provides for methods wherein the fruit of the plant is a plantain.

In some aspects, the présent disclosure provides for methods wherein the fruit ofthe plant is a Cavendish banana.

In some aspects, the présent disclosure provides for methods wherein the fruit of the plant is a latundan banana.

Herein it is given that any range or desired value given herein may be extended or altered without losing the effects sought, as is apparent to the skilled person for an understanding of the teachings herein.

5. EXAMPLES

The following synthetic and biological examples are offered to illustrate this the présent technology and are not to be construed in any way as limiting the scope of this the présent technology. Unless otherwise stated, ail températures are in degrees Celsius.

The examples are offered for illustrative purposes only, and are not intended to limit the scope ofthe présent invention in any way. Efforts hâve been made to ensure accuracy with respect to numbers used (e.g. amounts, températures, etc.), but some experimental errer and déviation should, of course, be allowed for.

The practice of the présent invention will employ, unless otherwise indicated, conventional methods of synthetic organic chemistry, protein chemistry and biochemistry and agriculture are within the skill of the art. Such techniques are explained fully in the literature. See, e.g. T. E. Creighton, Proteins: Structures and Molecular Properties (W. El. Freeman and Company, 1993); A. L. Lehninger, Biochemistry (Worth Publishers, Inc., current addition); Methods In Enzymology (S. Colowick and N. Kaplan eds., Academie Press, Inc.); Remington's Agricultural Sciences, 18th Edition (Easton, Pennsylvania: Mack Publishing Company, 1990); Carey and Sundberg Advanced Organic Chemistry 3^rd Ed. (Plénum Press) Vols A and B(1992), and Organic Reactions, Volumes 1-40 (John Wiley, and Sons, 1991).

The présent technology is lurther understood by reference to the following examples, which are intended to be purely exemplary of the présent technology. The présent technology is not limited in scope by the exemplified embodiments, which are intended as illustrations of single aspects of the présent technology only. Any methods that are functionally équivalent are within the scope of the présent technology. Various modifications of the présent technology in addition to those described herein will become apparent to those skilled in the art from the foregoing description and accompanying figures. Such modifications fall within the scope of the appended claims.

5.1. EXAMPLE 1: Field Uses

Field assessment against Mycosphaerella fijiensis

Trial 1 : Compound I was synthesized according to known methods in the art and test samples were obtained and formulated. A fungicidal treatment containing Compound I 10% EC (GF3645) at 25, 50, 75, 100, 150, 200 and 250 g ai/ha was applied with 40% v/v (adjuvant/treatment) of the adjuvant 50% Plurafac LF 1300 EC in order to ascertain efficacy against black sigatoka disease in banana, caused by Mycosphaerella fijiensis. When applied with 40% v/v (adjuvant/treatment) of 50% Plurafac LF 1300 EC adjuvant, 150, 200 and 250 g ai/ha of Compound I resulted in more commercially compétitive levels and in banana black sigatoka disease control. Results are from field trial TAFS17F05, which is archived in HARMONY under protocol number PA17X02016.

Trial TAFS17F05 was in a RCB design with 4 réplications. Trial was artifïcially inoculated and received two application timings on a ten-day interval with an application volume of 800 L/ha.

Trial TAFS 17F05, 2 Day Protectant (box-plot figure)

COMPOUND I EC Banana Black Sigatoka protectant TAFS

MYCOFI -21 DAAB

TAF517F0Ô

Msir « Les b&biv box. h&n±er c<ob=ar'£t©rssco’Ê box

HSD P=6.1 ^gai lia &mlpr lia

Trial 2: Compound I was synthesized according to known methods in the art and test samples were obtained and formulated. DHP Compound I (GF-3645) 10% EC on black Sigatoka control in banana, caused by Mycosphaerella fijiensis, on banana crop. Two single leaf trials were conducted in Guâpiles - Costa Rica between May - July 2017 that showed strong fungicidal activity of Compound I at 50, 100, 150 and 200 g ai/ha to control black Sigatoka disease on banana. Fungicide Compound I applied even at 100 g ai/ha showed excellent results in tenus of préventive and curative effect compared to commercial standards on black Sigatoka disease control in banana crop. Four rates of Compound I 10% EC (GF-3645) at 50, 100, 150 and 200 g ai/ha were mixed and tested with Minerai oil (7 L/Ha) in order to ascertain efficacy against black Sigatoka disease in banana. One treatment at 100 g ai/ha was tested with water, to observe the oil contribution. The effectiveness of Compound I at 100 g ai/Ha was similar or better in terms of curative and préventive effect than the main curative commercial standard Difenoconazole (Sico 25 EC). The mixed with Oil showed better performance than water. Results are from field trials ACF1718A & ACF1718B, which are archived in HARMONY under protocol number LAI 7X02050.

Trials ACF1718A & ACF1718B were done in a RCB design with 5 réplications. They were done under Single Leaf Test Methodology, with one application in leaf number 1 (to test préventive effect) and leaf number 3 (to test curative effect), with a volume application of 23 L/ha.

Summary across two trials about ACF1718A & ACF1718B, 30 Days after application (box-plot figure)

COMPOUND1 évaluation on MYCOFI contre! in banana crop. titeval.int - 30DAA1 pltparteval - LEAF 1

Claims (23)

1. A method of controlling or preventing fungal disease in a plant in the genus Musa, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, wherein Compound I is according to the structure:

2. A method of controlling or eradicating Mycosphaerella fijiensis fùngal pathogen in a plant, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, wherein Compound I is according to the structure:

3. A method of controlling or preventing fungal disease in a plant in the genus Musa, or controlling or eradicating Mycosphaerella fijiensis fungal pathogen in a plant, the method comprising contacting: an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and/or foliage of the plant, with a fungicide composition comprising a phytologically acceptable amount of Compound I, or a tautomer or sait thereof, and a carrier, wherein Compound I is according to the structure:

Compound I

4. The method of any one of claims 1-3, wherein the composition further comprises an agriculturally active ingrédient selected from the group consisting of: insecticide, an herbicide, and a fungicide.

5. The method of claim 3 or claim 4, wherein the carrier includes one or more of a thickener, emulsifier, rheology agent, dispersant and/or solid carrier.

6. The method of any one of claims 1-5, wherein the disease is black Sigatoka.

7. The method of any one of claims 1-5, wherein the disease is Tropical race 4 (TR4).

8. The method of any one of claims 1-5, wherein the disease is Banana bunchy top virus (BBTV) or Banana bacterial wilt (BBW).

9. The method of any one of claims 1-8, wherein Compound I is contacting a rate from 25-250 g ai/ha.

10. The method of any one of claims 1-8, wherein Compound I is contacting a rate of 50, 100, 150, 200 or 250 g ai/ha.

11. The method of any one of claims 1-8, wherein Compound I is contacting a rate of 100 g ai/ha.

12. The method of any one of claims 1-11, wherein the plant species is Musa acuminata or Musa balbisiana.

13. The method of any one of claims 1-11, wherein the plant species is Musa acuminata.

14. The method of any one of claims 1-11, wherein the plant species is Musa balbisiana.

15. The method of any one of claims 1-14, wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield from 2-90% by weight.

16. The method of any one of claims 1-14, wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 5% by weight.

17. The method of any one of claims 1-14, wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield by 50% by weight.

18. The method of any one of claims 1-14, wherein the disease or Mycosphaerella fijiensis fungal pathogen reduces fruit yield from 80% by weight.

19. The method of any one of claims 1-18, wherein the fruit ofthe plant is a plantain.

20. The method of any one of claims 1-18, wherein the fruit of the plant is a Cavendish banana.

21. The method of any one of claims 1-18, wherein the fruit of the plant is a latundan banana.

22. The method of any one of claims 1-21, wherein Compound I is according to the structure:

Compound I

23. The method of any one of claims 1-21, wherein Compound I is according to the structure: