阅读说明：本技术 二氟-(2-羟丙基)吡啶化合物作为黑叶斑病的杀真菌剂 (Difluoro- (2-hydroxypropyl) pyridine compounds as fungicides of melasma ) 是由 A·C·拉米雷斯 C·盖洛普 C·E·罗哈斯·卡尔沃 E·E·波萨达 黄一修 于 2020-03-03 设计创作，主要内容包括：本公开涉及农用化学品领域,具体而言,本公开提供了杀真菌化合物I及其在控制芭蕉属植物疾病中的用途。(The present disclosure relates to the field of agrochemicals, in particular, the disclosure provides fungicidal compound I and its use in the control of disease in musa plants.)

1. A method of controlling or preventing fungal disease in plants of the musa genus, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting the growth of the plant, roots of the plant and/or leaves of the plant with a phytologically acceptable amount of compound I, or a tautomer or salt thereof, wherein compound I is according to the structure:

2. a method of controlling or eradicating a myrothecium virescens (Mycosphaerella fijiensis) fungal pathogen in a plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting the growth of the plant, roots of the plant and/or leaves of the plant with a phytologically acceptable amount of compound I, or a tautomer or salt thereof, wherein compound I is according to the structure:

3. a method of controlling or preventing a fungal disease in a plant of the musa genus, or controlling or eradicating a fungal pathogen of myrothecium scabra in a plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting growth of the plant, roots of the plant and/or leaves of the plant with a fungicide composition comprising an phytologically acceptable amount of compound I or a tautomer or salt thereof and a carrier, wherein compound I is according to the following structure:

4. the method of any one of claims 1-3, wherein the composition further comprises an agriculturally active ingredient selected from the group consisting of: insecticides, herbicides and fungicides.

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

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

7. The method of any one of claims 1-5, wherein the disease is tropical small size 4 (TR 4).

8. The method of any one of claims 1-5, wherein the disease is Banana Bunchy Top Virus (BBTV) or banana bacterial wilt disease (BBW).

9. The method of any one of claims 1-8, wherein the contact rate of compound I is 25-250g ai/ha.

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

11. The method of any one of claims 1-8, wherein the contact rate of compound I is 100g ai/ha.

12. The method of any one of claims 1-11, wherein the plant species is Musa microphylla (Musa acuminata) or Musa basjoo (Musa basbian).

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

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

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

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

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

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

19. The method of any one of claims 1-18, wherein the fruit of the plant is 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 radon banana.

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

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

2. Background of the invention

Fungicides are compounds of natural or synthetic origin which act to protect and treat plants against damage caused by agriculturally relevant fungi. Generally, no one fungicide is useful in all cases. Especially, the fungus of the banana black stripe fungus (Mycosphaerella fijiensis) has adverse effect on crops such as bananas. Accordingly, research is being conducted to produce fungicidal compounds that may have better performance, are easier to use, and are less costly.

3. Summary of the invention

The compounds I are known as fungicidal compounds. The structure of the compound is:

the chemical name of compound I is also known: 4- ((6- (2- (2, 4-difluorophenyl) -1, 1-difluoro-2-hydroxy-3- (5-thio-4, 5-dihydro-1H-1, 2, 4-triazol-1-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 incorporated herein by reference in its entirety.

Black Sigatoka (black Sigatoka) is one of the most serious diseases that harm banana crops worldwide. Almost all banana leaf parts are affected by this pathogen. As a new triazole on this market, compound I provides a very important tool for controlling this disease in bananas.

In general, the present disclosure relates to compound I and its use as a plantain fungicide. The compound I is found to be particularly active against the fungus Musa sapiensis. In particular, compound I provides excellent protection against fungal pathogens causing Black Leaf Spot (BLSD) or black leaf spot. However, compound I is also active against other fungal and other plant diseases.

In one aspect, the present disclosure provides a method of controlling or preventing a pathogen-induced disease in a plantain plant. Such plants are at risk of being pathogenic by pathogens such as black stripe banana. In some such aspects, the disclosure herein provides a method of controlling or preventing black leaf spot or black stripe spot (BLSD) in a plant, the method comprising treating the plant or an area adjacent to the plant with compound I or a composition comprising compound I.

In some aspects, the present disclosure provides methods of controlling or eradicating a banana myrtle pathogen. In such an aspect, the progression of the disease may or may not be prevented, but the pathogen may be removed. Furthermore, in such aspects, compound I is specific for alternaria bananas. This means that compound I is active specifically against this pathogen, but may also be less effective or efficient against other pathogens. For example, compound I can kill almost all of the existing sigatoka fungus, but only 10%, 20%, 30%, 40%, 50%, 60%, 70%, 75%, 80%, 85% or 90% of other fungi, such as the fungi anthracnose avenae (Colletotrichum cereale) and/or Verticillium dahliae (Verticillium dahliae), can be killed at the same time (either in or on the same plant). Thus, compound I is selective for alternaria bananas.

In some aspects, the present disclosure provides methods of controlling or eradicating other biologically relevant fungi in plantain plants, including mycosphaerella banana (m.musicola), pyricularia banana (heliotropum torulosum), and/or Pestalotia leprogena.

In some aspects, the present disclosure provides a method or use of compound I for protecting a plant from attack by, or treating a plant infested by, a phytopathogenic organism (myrothecium lanuginosum), comprising applying compound I, or a composition comprising compound I, to soil, a plant, a part of a plant, foliage and/or seeds.

In some aspects, the present disclosure provides a method for controlling or preventing a fungal disease in a plantain plant, the method comprising treating the plant or an area adjacent to the plant with compound I or a composition comprising compound I. In some of these aspects, the disease is black leaf spot. In some of these aspects, the disease is black leaf spot. In some of these aspects, the disease is Tropical race 4 (Tropical race 4, TR 4).

In some aspects, the present disclosure provides compositions for protecting plants from and/or treating plants infected with alternaria bananas, the compositions comprising a phytologically acceptable amount of compound I and a carrier material. In such aspects, the components of the compositions and the manufacture thereof are well known in the art as phytological or fungicidal compositions, and the carriers therefor are described extensively in a number of primary references, including those disclosed herein.

In some aspects, the present disclosure provides compositions comprising compound I and an active. In such aspects, the active substance is an ingredient having agricultural activity. Ingredients having agricultural activity include, but certainly are not limited to, existing or known insecticides, herbicides, and fungicides.

4. Detailed description of the preferred embodiments

4.1. Definition of

Unless explicitly defined otherwise in the present disclosure, various terms used in the specification and claims herein are defined as follows. All technical and scientific terms not defined herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

As used herein, the term "salt" refers to salts suitable for use in agriculture, i.e., they affect humans and lower animals without excessive toxicity, irritation, allergic 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 salts derived from suitable inorganic and organic acids and bases. Examples of acid addition salts are salts of amino groups formed with inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid and perchloric acid, or 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, adipates, alginates, ascorbates, aspartates, benzenesulfonates, benzoates, bisulfates, borates, butyrates, camphorates, camphorsulfonates, citrates, cyclopentanepropionates, digluconates, dodecylsulfates, ethanesulfonates, formates, fumarates, glucoheptanoates, glycerophosphates, gluconates, hemisulfates, heptanoates, hexanoates, hydroiodides, 2-hydroxyethanesulfonates, lactobionates, lactates, laurates, malates, maleates, malonates, methanesulfonates, 2-naphthalenesulfonates, nicotinates, nitrates, oleates, oxalates, palmitates, pamoates, pectinates, persulfates, 3-phenylpropionates, phosphates, Pivalate, propionate, stearate, succinate, sulfate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate and the like. Salts derived from suitable bases include alkali metal, alkaline earth metal, ammonium salts. Representative alkali or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium, and the like. Further pharmaceutically acceptable salts include, when appropriate, non-toxic ammonium, quaternary ammonium and amine cations formed using counterions such as halide, hydroxide, carboxylate, sulfate, phosphate, nitrate, lower alkyl sulfonate and aryl sulfonate.

"tautomers" refer to alternative forms of compounds that differ in the position of the proton, such as enol-ketone and imine-enamine tautomers, or tautomeric forms of heteroaryl groups containing ring atoms attached to the ring NH moiety and the 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 a plant disease that it is desired to control, but that is not significantly toxic to the plant. This amount is generally from about 0.1 to about 1000ppm (parts per million), preferably from 1 to 500 ppm. The exact concentration of the desired compound will vary with the fungal disease to be controlled, the type of formulation usedType, method of application, particular plant species, climatic conditions, etc. Suitable application rates are generally from about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g/m)²)。

The term "disease-inhibiting and phytologically acceptable amount" refers to an amount of a compound that kills or inhibits a plant disease that it is desired to control, but that is not significantly toxic to the plant. This amount is generally from about 0.1 to about 1000ppm (parts per million), preferably from 1 to 500 ppm. The exact concentration of the desired compound will vary with the fungal disease to be controlled, the type of formulation used, the method of application, the particular plant species, the climatic conditions, and the like. Suitable application rates are generally from about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g/m)²)。

4.2. Additional explanation conventions

In general, reference to or description of an element, such as hydrogen or H, is intended to include all isotopes of that element. For example, if an R group is defined to include hydrogen or H, it also includes deuterium and tritium. Thus, containing tritium, for example,¹⁴C、³²P and³⁵compounds that are radioisotopes of S are within the scope of the present technology. The manipulations for inserting such labels into the compounds of the present technology will be apparent to those skilled in the art based on the disclosure herein.

Unless a particular stereochemistry is explicitly indicated, all chiral, diastereomeric and racemic forms of a compound are intended. Thus, the compounds described herein include enriched or resolved optical isomers at any or all asymmetric atoms, as is apparent from the description. Racemic mixtures and d or l enriched stereoisomeric mixtures as well as individual optical isomers may be separated or synthesized so as to be substantially free of their enantiomeric or diastereomeric partners, and such stereoisomers are within the scope of the present technology.

The compounds described herein may exist as solvates, especially hydrates, and all such solvates and hydrates are contemplated unless otherwise specified. Hydrates can form during the manufacture of the compounds or compositions containing these compounds, or hydrates can form over time due to the hygroscopic nature of the compounds. The compounds of the present technology may also exist as organic solvates, including DMF, ether, and alcohol solvates, and the like. The identification and preparation of any particular solvate is within the skill of one of ordinary skill in synthetic organic or pharmaceutical chemistry.

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

For the purposes of this specification and the appended claims, unless otherwise indicated, all numbers expressing quantities, sizes, dimensions, proportions, shapes, formulae, parameters, percentages, parameters, quantities, characteristics, and other numerical values used in the specification and claims are to be understood as being modified in all 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 specification and attached claims are not and need not be exact, but may be approximate and/or larger or smaller as desired, reflecting tolerances, 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, when values are mentioned, the term "about" may be intended to include variations from the specified values of ± 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% in some aspects, and ± 0.1% in some aspects, so long as such variations are suitable for performing the disclosed methods or using the disclosed compositions.

As used herein and in the appended claims, the singular articles such as "a," "an," and "the" and similar referents in the context of describing the elements (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 limits of the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All 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 all examples, or exemplary language (e.g., "such as") provided herein, is intended merely to better illuminate embodiments and does not pose a limitation on the scope of the claims unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential.

4.3. Methods of control or prevention

4.3.1. Disease and disorder

In some aspects, the present disclosure provides methods of controlling or preventing disease in a plantain plant. In some aspects, the present disclosure provides methods of controlling or preventing a fungal disease in a plantain plant, the method comprising treating the plant or an area adjacent to the plant with compound I, or a tautomer or salt thereof, or a composition comprising compound I.

In some aspects, the present disclosure provides methods of controlling or preventing a fungal disease in a plantain plant, the method comprising contacting the plant or a region adjacent to the plant with compound I:

or a tautomer or salt thereof.

In some aspects, the present disclosure provides methods of controlling or preventing a fungal disease in a musa plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting the growth of the plant, roots of the plant and/or leaves of the plant with a phytologically acceptable amount of compound I, or a tautomer or salt thereof, wherein compound I is according to the structure:

in some aspects, the present disclosure provides methods of controlling or preventing a fungal disease in a musa plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides methods of controlling or preventing sigatoka in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides methods of controlling or preventing sigatoka in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides a method of controlling or preventing banana bacterial wilt disease (BBW) in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some of these aspects, the disease is black leaf spot. In some of these aspects, the disease is banana bacterial wilt disease (BBW). In some aspects, the disease is tropical # 4 race (TR 4). In some aspects, the disease is Banana Bunchy Top Virus (BBTV).

In some aspects, the present disclosure provides methods, wherein compound I is according to the structure:in some aspects, the present disclosure provides methods, wherein compound I is according to the structure:

4.3.2. fungi

In some aspects, the present disclosure provides methods of controlling or preventing an attack by a fungal pathogen of myrothecium lanuginosum.

In some aspects, the present disclosure provides methods of controlling or eradicating a fungal pathogen of alternaria bananas in a plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting the growth of the plant, roots of the plant and/or leaves of the plant with a phytologically acceptable amount of compound I, or a tautomer or salt thereof, wherein compound I is according to the structure:

in some aspects, the present disclosure provides methods of controlling or eradicating a fungal pathogen of alternaria bananas in a plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides methods of controlling or eradicating a sigatoka fungus pathogen in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides methods of controlling or eradicating one or more pathogens in mycosphaerella banana, pyricularia banana and/or peptalotia leprogena in a banana plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting growth of the plant, roots of the plant and/or leaves 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 salt thereof, and a carrier, wherein compound I is according to the following structure:

in some aspects, the present disclosure provides methods of controlling or eradicating one or more pathogens in mycosphaerella banana, pyricularia banana and/or peptalotia leprogena in a banana plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting growth of the plant, roots of the plant and/or leaves 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 salt thereof, and a carrier, wherein compound I is according to the following structure:

or a tautomer or salt thereof.

In some aspects, the pathogen is banana mycosphaerella. In some aspects, the pathogen is pyricularia banana. In some aspects, the pathogen is peptalotia leprogena.

A method of controlling or preventing a fungal disease in a plant of the musa genus, or controlling or eradicating a fungal pathogen of myrothecium scabra in a plant, the method comprising: contacting an area adjacent to the plant, soil suitable for supporting growth of the plant, roots of the plant and/or leaves of the plant with a fungicide composition comprising an phytologically acceptable amount of compound I or a tautomer or salt thereof and a carrier, wherein compound I is according to the following structure:

4.3.3. composition comprising a metal oxide and a metal oxide

In some aspects, the present disclosure provides methods wherein the composition further comprises an agriculturally active ingredient selected from the group consisting of: insecticides, herbicides and fungicides.

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

In some aspects, the present disclosure provides methods wherein the composition carrier comprises one or more of a thickener, an emulsifier, a rheological agent, a dispersant, and/or a solid carrier.

In various aspects, compound I is applied by any of a variety of known techniques, either as compound I or as a formulation comprising compound I. For example, compound I can be applied to the roots, seeds, stems, flowers or leaves of plants for controlling various fungi without compromising the commercial value of the plants. Compound I can also be applied as foliar spray, soil drench, soil injection, seed treatment, or in water in aquaculture and floating nursery trays. The substances may be applied in the form of any of the formulation types commonly used, for example as solutions, dusts, wettable powders, flowable concentrates or emulsifiable concentrates.

Preferably, compound I of the present disclosure is applied in the form of a formulation comprising compound I with a phytologically acceptable carrier. The concentrated formulation may be applied by dispersion in water or other liquid, or the formulation may be in powder or granular form and then applied without further treatment. The formulations may be prepared according to procedures conventional in the agrochemical art.

The present disclosure contemplates all carriers or vehicles by which compound I can be formulated for delivery and use as fungicides. That is, the formulations disclosed, contemplated, and intended to all work with formula I include all carriers that one of skill in the art would use in agricultural fungicide formulations. Typically, the formulations are applied in the form of an aqueous suspension or emulsion. Such suspensions or emulsions may be made from water-soluble, water-suspendable or emulsifiable formulations, which are solids (commonly referred to as wettable powders); or a liquid (often referred to as an emulsifiable concentrate, an aqueous suspension, or a suspension concentrate). As will be readily appreciated, any material to which compound I can be added can be used, provided that the material produces the desired effect without significantly interfering with the activity of compound I as an antifungal agent.

Wettable powders that can be compacted to form water dispersible granules comprise an intimate mixture comprising compound I, an inert carrier and a surfactant. The concentration of compound I in the wettable powder may be from about 10% to about 90% by weight, more preferably from about 25% to about 75% by weight, based on the total weight of the wettable powder. In the preparation of wettable powder formulations, compound I can be compounded with any finely divided solid, such as pyrophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite, diatomaceous earth, purified silicates, etc. In such operations, finely divided carriers and surfactants are typically blended with compound I and milled.

Emulsifiable concentrates of compound I can comprise compound I in a suitable liquid at a suitable concentration, for example, from about 10% to about 50% by weight, based on the total weight of the concentrate. Compound I may be dissolved in an inert carrier, which is a mixture with a water-miscible solvent or with a water-immiscible organic solvent, and an emulsifier. The concentrate may be diluted with water and oil to form a spray mixture in the form of an oil-in-water emulsion. Useful organic solvents include aromatic compounds, especially the high boiling naphthalene and olefinic portions of petroleum, such as heavy aromatic naphtha. Other organic solvents may also be used, for example, terpene solvents (including rosin derivatives), aliphatic ketones (such as cyclohexanone), and complex alcohols (such as 2-ethoxyethanol).

Emulsifiers that may be advantageously used herein can be readily determined by one skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or blends of two or more emulsifiers. Examples of nonionic emulsifiers that can be used to prepare the emulsifiable concentrates include polyalkylene glycol ethers and the condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide (e.g., ethoxylated alkyl phenols) and carboxylic acid esters dissolved with polyhydric alcohols or polyalkylene oxides. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkylaryl sulfonic acids (e.g., calcium), oil-soluble salts or sulfated polyglycol ethers and suitable salts of phosphated polyglycol ethers.

Representative organic liquids that can be used to prepare emulsifiable concentrates of compound I of the present invention are aromatic liquids, such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids, such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, especially dimethylamides and glycol derivatives of fatty glycols, such as the n-butyl, ethyl or methyl ethers of diethylene glycol, the methyl ether of triethylene glycol, and the like. Mixtures of two or more organic liquids may also be used in the preparation of the emulsifiable concentrate. The organic liquid includes xylene, and propylbenzene fractions, with xylene being most preferred in some cases. Surface-active dispersants are generally used in liquid formulations in amounts of from 0.1 to 20% by weight, based on the total weight of dispersant and compound I. The formulations may also contain other compatible additives such as plant growth additive regulators and other biologically active compounds used in agriculture.

An aqueous suspension including compound I may be dispersed in an aqueous vehicle at a concentration of about 5 wt.% to about 50 wt.%, based on the total weight of the aqueous suspension. The suspension was prepared by: compound I was finely milled and the milled material was vigorously mixed into a vehicle comprising water and a surfactant selected 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 can also be applied in the form of granular formulations, which are particularly useful for application to soil. The granular formulations typically contain from about 0.5% to about 10% by weight, based on the total weight of the granular formulation of compound I, dispersed in an inert carrier consisting entirely or mostly of coarsely dispersed inert materials such as attapulgite, bentonite, diatomaceous earth, clays or similar inexpensive materials. Such formulations are typically prepared by dissolving compound I in a suitable solvent and applying it to a particulate carrier that has been pre-shaped to an appropriate particle size of about 0.5mm to about 3 mm. Suitable solvents are those in which compound I is substantially or completely soluble. Such formulations can also be prepared by making a dough or paste of the carrier and compound I and solvent and pressing and drying to obtain the desired granular particles.

Dusts containing compound I are prepared by intimately mixing compound I in powder form with a suitable powdered agricultural carrier, such as, for example, kaolin, ground volcanic rock, and the like. The powder may suitably contain from about 1% to about 10% by weight of compound I, based on the total weight of the powder.

The formulations may additionally contain auxiliary surfactants to enhance deposition, wetting and penetration of compound I on target crops and organisms. These co-surfactants can optionally be used as components of a formulation or as a tank mix. The amount of co-surfactant will generally vary from 0.01 to 1.0 volume%, preferably from 0.05 to 0.5 volume%, based on the volume of water sprayed. Suitable adjunct surfactants include, but are not limited to, ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, salts of esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, and blends of surfactants with mineral or vegetable oils. The formulations may also include oil-in-water emulsions, such as those disclosed in U.S. patent application serial No. 11/495,228, the disclosure of which is expressly incorporated by reference into this application.

In some cases, it would be beneficial to spray formulations of the current compositions by aerial spray using an airplane or helicopter. The exact composition of these aerial sprays depends on the crop being treated. Aerial spraying of cereals utilizes a spray volume of preferably 15 to 25L/ha, with standard diffusion or penetration type aids, such as nonionic surfactants or crop oil concentrates, preferably 0.05% to 15% based on the spray volume of water. Aerial spraying of fruit crops, such as bananas, can be carried out using lower application rates and higher adjuvant concentrations, preferably in the form of adhesion aids, such as fatty acids, latex, fatty alcohols, crop oils and mineral oils. Typical spray volumes for fruit crops are preferably from 15 to 30L/ha, with adjuvant concentrations of up to 30% based on the spray volume of water. Typical examples may include, but are not limited to, 23L/ha application, 30% paraffin oil adhesion aid concentration (e.g., Spraytex CT).

Methods of making and using these agricultural compositions comprising compound I can be found, for example, in references such as Hance et al, Weed Control Handbook (8th ed., Blackwell Scientific, Oxford,1989) [ herbicidal Handbook (8th edition, blakewell science, Oxford,1989) ] and Mollet, h, and grubmann, a.: formulation technology (Wiley VCH Verlag [ Willi VCH book, Inc.; Weinheim,2001, Perry's Chemical Engineers ' Handbook,4th Ed., McGraw-Hill [ Pary Chemical Engineers ' Handbook,4th edition, Mcago-Hill ], New York, 1963, Browning et al, "agglomerization" in Chemical Engineering [ Agglomeration "in Chemical Engineering ], 12 months 4 days 1967, 147-48, Klingman, Weed Control as a Science [ Weed Control Science ] (J.Wiley & Sons [ John Willi-Gilg, 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 707445, GB 2,095,558 and WO 9113546, each of which is incorporated herein by reference in its entirety.

Each of the methods disclosed herein is contemplated for use with any of the formulations described herein, and the formulations may optionally include combinations containing other pesticidal compounds. Such additional pesticidal compounds may be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactericides, or combinations thereof that are compatible with the compounds of the present invention in the medium selected for application and that do not antagonize the activity of the compounds of the present invention. Thus, in such embodiments, another pesticidal compound is used as a supplemental toxicant for the same or a different pesticidal use. The compound I and the pesticidal compound in the combination may generally be present in a weight ratio of from 1:100 to 100: 1.

The compounds of the present disclosure may also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The compounds I of the present disclosure are typically applied in combination with one or more other fungicides to control a wider range of undesirable diseases. When used in combination with one or more other fungicides, the claimed compounds I can 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- (thiocyanomethyl) -benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, ametocin, antimycin, Ampelomyces graminis (Ampelomyces quisqualis), azaconazole, azoxystrobin, Bacillus subtilis (Bacillus subtilis), Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalinate, benzylaminophenyl-sulfonic acid (BABS) salt, bicarbonate, biphenyl, thiconazole, bitertanol, bixafen, blasticidin, borax, poldol mixture, boscalid, bromconazole, bupirimate, calcium polysulphide, captafol, captan, carbendazim, carboxin, cyclopropanamide, carvone, clofencholone (chlazafenone), disolfen, chlorothalonil, chlozolinum, chloester (Coniothyrium), copper hydroxide, copper octoate, pyrimethanil, amethyol, amethoxide, amethone, benomyl, thixene, copper hydroxide, copper carbonate, copper, Copper oxychloride, copper sulfate, copper hydroxide sulfate, cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, prochloraz, diamineethylenebis- (dithiocarbamate), dichlofluanid, dichlorfluanid, diclorfenamid, pyridaben, niclosamide, diethofencarb, difenoconazole, difenzoquat (difenozoquat), difluoroforest, dimethomorph, dimoxystrobin, diniconazole-M, fenaminostrobin, dinocap, diphenylamine, dithianon, moroxydianon, moroxydine acetate, dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, hymexazol, famoxadone, fenamidone, fenaminophenicol, fenbuconazole, fenfuramide, fenpyrad, fenpiclonidine, fenpropidin, fenpropimorph, fenpyrad, fenpyrazamide, fenpyrazamine, fenpyrazamide, fenpyroxim, fenbutazone, fenpyrazamide, fenpyrazamine, fenbutazone, fenpropimorph, fenpyrazamide, fenpyrazamine, fenpyraflufen-p-N-p-ethyl, fenbutazone, fenflurazoxystrobin, fenbutazone, fenflurazoxystrobin, fenpyrazal, fenpyraflufen, fenpyraclostrobin, fenpyrad, fenpyraclostrobin, fenpyrad-p-n, and so as-p, Fentin, ferbam, azoxystrobin, fluazinam, fludioxonil, flurbipyramid, flumorph, fluopyram, furazolidone, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, fluthianide (fluthianil), flutolanil, flutriafol, fluxapyroxamid, folpet, formaldehyde, ethylphosphonic acid, fosetyl-aluminum, fuberidazole, furalaxyl, furazofamide, biguanide salt acetate, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil sulfate, imibenconazole, iminoctadine triacetate, iminoctadine, ipconazole, ipfenpyrone, iprobenfazone, iprobenfos, iprodione, propineb, isoprothiolane, isothiocamycin, kasugamycin hydrochloride, thiofam (acetate), thiocarb, fenpropineb, fenpyraclostrobin, fluazin, fluazinam, fenpropineb, fenpyraclostrobin, fluazinam, fenpropineb hydrate, fenpropineb, fenpropiconazole, mancozeb, mandipropamid, maneb, metalaxyl-M, mepanipyrim, mefenamate, dinocap, mercuric chloride, mercuric oxide, calomel, metalaxyl-M, metam (metam), metam-Potasicum, metam-sodium, metconazole, sulbencarb, methyl iodide, dichloline, metiram, metominostrobin, metrafenone, milomycin, myclobutanil, sodium metiram, phthalazinol, octreoketone, meturamide, oleic acid (fatty acid), orysastrobin, oxadixyl, oxine-copper, imidazole fumarate, carboxin oxide, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercuric acetate, phosphonic acid, tetrachlorophthalide, picoxystrobin, polyoxin B, doxycycline, nixin, quintocin, potassium hydroxide, quinoline, potassium hydroxide, quintocin, meprobamate, Thiabendazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, propoxymidone, prothioconazole, pyraclostrobin, pyrifenocarb, pyributicarb, pyribenzoxim, pyrimethanil, meptylidine, pyroquilon, quinozalone, quinoxyfen, quintozene, giant knotweed (Reynouria sachalinensis) extract, epoxiconazole, Thiosilicamide, simeconazole, 2-phenylphenol sodium, sodium bicarbonate, pentachlorophenol sodium, spiroxamine, sulfur, SYP-Z048, coal tar, tebuconazole, fluoroquinol (tebuflofen), tetraoxynitrobenzene, tetraconazole, thiabendazole, thifluzamide, thiophanate methyl, thiram, tiadinil, tolclofos-methyl, tolbutamol, triadimefon, trifloxystrobin, flutriafolacin, fluazin, trifloxystrobin, Triticonazole, validamycin, lambda-cyhalothrin, propamocarb, benomyl, zineb, ziram, zoxamide, Candida (Candida oleophila), Fusarium oxysporum (Fusarium oxysporum), Gliocladium species, coriolus versicolor (phorbiopsis gigantea), Streptomyces griseoviridis (Streptomyces griseoviris), Trichoderma species (Trichoderma), (RS) -N- (3, 5-dichlorophenyl) -2- (methoxymethyl) -succinimide, 1, 2-dichloropropane, 1, 3-dichloro-1, 1,3, 3-tetrafluoroacetone hydrate, 1-chloro-2, 4-dinitronaphthalene, 1-chloro-2-nitropropane, 2- (2-heptadecyl-2-imidazolin-1-yl) ethanol, 2, 3-dihydro-5-phenyl-1, 4-dithia-1, 1,4, 4-tetraoxide, 2-methoxyethyl mercury acetate, 2-methoxyethyl mercury chloride, 2-methoxyethyl mercury silicate, 3- (4-chlorophenyl) -5-methylrhodanine, 4- (2-nitroprop-1-enyl) phenyl thiocyanate, alanine phosphonic acid, propamocarb, thiram oxide, barium polysulfide, Bayer 32394, puccinia, dithizone, profenuron (bentaluron), and benzyl enoate (benzamicril); isobutyl benzoenoate, buthioline, benzovindiflupyr, binapacryl, dimethenamid sulfate, bis (methylmercury), bis (tributyltin) oxide, buthionine, herbicidium, mycophenolate, CECA, fenbuconazole, prodiamine, benzimidazole, tetrachloroquinoxaline, climbazole, bis (3-phenylsalicylate) copper, copper zinc chromate, coumoxystrobin, thiabendazole, copper oxychloride, cyclofuroamide, cyhalonil, esteram, fosfamid, dichlorobenzothiazole, dichloronaphthoquinone, sclerotium, chlorotriazolol, metidine, diuron, nitrooctyl, nitrobutyl, dipyrmetitrone, pyrithione, pyrithion, sterile phosphorus, doxycycline, fenaminostrobilus, EBP, trifloxystrobin, ESBP, epoxiconazole, metiram, ethirimol (ethirimm), sodium sulfadiazine, fenamidothion, fenfurazoate, trifloxystrobin, furbenconazole, flufurbenconazole, flufenazamide, triflumizole, fenamidone, trifloxystrobin, triflumizole, cloxacarb, clofenamidone, furbenfurbenconazole, flufenamidone, flutriafolpet, flubenconazole, flubensulbenconazole, flubenconazole, benconazole, bensulbensulbensulbensulbensulbenfurbenconazole, benconazole, benfurbenfurbenfurbenfurbenconazole, benconazole, benfurbenconazole, benconazole, benfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenfurbenconazole, benfurbenfurbenconazole, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenfurbenconazole, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenconazole, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenconazole, benfurbenfurbenfurbenfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenconazole, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenconazole, benconazole, benfurbenfurbenfurbenfurbenfurbensulam, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbensulam, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbensulam, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfur, Fenpyrad, furametryn, glyodin, griseofulvin, quinolinylacrylate, Hercules3944, cyclohexaphos, ICIA0858, ipfentrifluconazole, iprothianum (isofenamid), isopimazapine (isopamphos), isovaledione (isovaledione), mandesstrobin, anthranilamide, mefenfenamide, flurbiprofen, hydralazide (metazoxolon), furametpyr, metalaxyl, tiadinium, metiram, thifenhexamide, metiram, tranexamic anhydride, metraline, N-3, 5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercuric-4-toluenesulfonanilide, nickel bis (dimethyldithiocarbamate), OCH, fluorothiazolepyrone, dimercaptophenmercuric benzoate, phenylmercuric nitrate, chlorophosphorous chloride, thiocarb; prochloraz, fluxapyroxad, pyraclostrobin, pyroflunomide (pyraziflumumid), picolonitrile, pyrisoxazole, prochloraz, fluridone, quinocetone sulfate, fenzopyr, fluquinconazole, quinquefolin (quinofunelin), pyrimidazole, salicylanilide, SSF-109, pentaphenylsulfone, thiophanate (tecoram), thiadifluoro, thiafipronil, thiophanate, carbomite, thiocyanobenzamide (tioxymid), triazophosphamide, cyprodinol, phyllotaite, trichlamide, clorac-methyl, trifloxystrobin, triflumuron, thiram, cyanamid, and any combination thereof.

Furthermore, compound I of the present invention can be combined with other pesticides (including insecticides, nematocides, acaricides, arthropodicides, bactericides or combinations thereof) that are compatible with compound I of the present invention and do not antagonize the activity of compound I in the medium selected for application to form pesticidal mixtures and synergistic mixtures thereof. Compound I of the present disclosure may be applied in combination with one or more other pesticides to control a wider range of undesirable pests. When used in combination with other pesticides, the presently claimed compounds I may be formulated with other pesticide(s), tank mixed with other pesticide(s) or applied sequentially with other pesticide(s). Typical insecticides include, but are not limited to: 1, 2-dichloropropane, abamectin, acephate, acetamiprid, housefly phosphorus, acetoprole, fluoropropylene, acrylonitrile, bollworm, aldicarb, aldelin, allethrin, alodamycin, methomyl, alpha-cypermethrin, alpha-ecdysone, alpha-endosulfan, thion, methiocarb, malathion, amifostine oxalate, amitraz, anabasine, ethoprophos, azadirachtin, piridophos-methyl, glutethion-methyl, azophos, barium hexafluorosilicate, piperethrin, bendiocarb, benfuracarb, benfuraphenthrin, bifenthrin, bioallethrin, bistrifluron, borax, boric acid, bromophenylphosphine, bromoxynil, bromo-DDT, Bromophos, ethylbromophos, thiocarb, buprofezin, carbofuran, temephos (butathiofos), carbobutanone, butoxyfop, ketoprofen, cadusafos, calcium arsenate, calcium polysulfide, toxaphene, cloxacarb, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, triphosphoric acid, carbosulfan, cartap hydrochloride, chlorantraniliprole, borneolum, chlordane, kaempferia, chlorfenamidine, chlorfenamidinium hydrochloride, phosphorus oxychloride, chlorfenapyr, chlorfluazuron, chlorfenapyr, chlorofos, chlormephos, chlorpyrifos-methyl, chlorfenafos, tebufenozide, guaethrin I, guaethrin II, guaethrin, cis-resmethrin, benfuracarb, closanticamine, thionine, copper arsenite, copper naphthenate, copper oleate, cudweed, coumaphos, croton, crotamion, amiton, etc, Croton, fenprophos, cryolite, cyanophos, cyhalothrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, methidathion, DDT, monomethyl carbofuran, deltamethrin, tianlephos-O, tianlephos-S, systemic phosphorus, methyl systemic phosphorus, systemic phosphorus-O-methyl, systemic phosphorus-S-methyl, phosphorus-N-methyl, diafenthiuron, diatomaceous earth, diazinon, isochlorothion, dichlofenphos, dichlorvos, dicyclanil, dieldrin, dinotefuran, dyzone, dimefluthrin, flumethrin, dimethoate, bendiocarb, fenpropathrin, methomyl, fenpropathrin, dichlorvos, dinotefuran, dimesnares, dimethoate, p, dimethoate, p, dimethoate, p, dimethoate, p, dimethoate, D, dimethoate, D, p, D, dinex-diclex, benfurazone, penitrol, dinotefuran, benfenoether, bensulide, dioxacarb, fenamiphos, disulfoton, thiotepa, d-limonene, DNOC-ammonium, DNOC-potassium, DNOC-sodium, doramectin, ecdysterone, emamectin benzoate, EMPC, empenthrin, endosulfan, endrin, EPN, bazaether, eprinomectin, allethrin (esdexpall thrine), esfenvalerate, etaphos (etaphos), ethiofencarb, ethiprole, fenaminostrobilus, ethylene dibromide, ethylene dichloride, ethylene oxide, ethofenprox, emithion, EXD, sulfamophos, fenamiphos, miticide, chlorophos, fenclofos, fenobuconazole, fenoxycarb, fenthion, fenpropathrin, fenbutachlor, pyraflufen-ethyl, pyrazamine, pyrazofen, pyraflufen, chlorpyrim, chlorpyrifos, pyraflufen, chlorpyrifos, and chlorpyrifos, etc, Fenpropathrin, fenprophos, fenpropathrin, fipronil, flonicamid, flubendiamide, flucloxacillin, flucycloxuron, flucythrinate, cyhalothrin, pyriminostrobin, flufenoxuron, trifluorethofenprox, cyfluthrin, disulfoton, vaboxamidine hydrochloride, anguo, acantho, fenthion, fosaprepin, vadanum, furdiocarb, furfluthrin, gamma-trichloroflucythrinate, gamma-HCH, proffluthrin, chlorfenozide, HCH, HEOD, heptachlor, heptenophos, sufenthion, hexaflumuron, HHDN, hydramethylhydrazone, hydrogen cyanide, methoprene, quinolinecarb, imidacloprid, prallethrin, indoxacarb, methyl iodide, IPSP, chlordiazepoxide, isochlorofen, isocoryfos, isoxate, isoxathion, isoprocarb, isoproxil, isoprothiolane, and so, Ivermectin, jasminoidin I, jasminoidin II, iodophos, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorolane, methoprene, lambda-cyhalothrin, lead arsenate, lepimedin, bromophenyl, lindane, propithion, lufenuron, fosthiazate, malathion, propionitrile, triazophos, methidathion, bentazon, dithiafos, mercurous chloride, fenthion sulfoxide, metaflumizone, chlorfenvinphos, methamidophos, methidathion, methiocarb, monocrotophos, methomyl, methoprene, mechlorethamine, methoxyfenozide, methyl bromide, methyl isothiocyanate, methylchloroform, methylene chloride, metofluthrin, metolcarb, methidathion, metolcarb, monocarb, milbemycin, propaphos, mone, monocrotophos, phoxim, phyton, promonol, monocrotophos, phoxim, monocrotophos, methomyl, Monosultap (monosultap), dicyclopentado, moxidectin, naphthylate, phosphorus dibromide, naphthalene, nicotine, nifolipine, nitenpyram, nithiazine, formoxyl, novaluron, noviflumuron, oxyfluor, oxamyl, oxydisulfuron, sulfothion, sulfofenthion, paradichlorobenzene, parathion, methyl parathion, chlorfluazuron, pentachlorophenol, promethirine, fenthion, phenothrin, phenthoate, phorate, phosmet, parathion, phosphamidon, phosphine, phoxim, methyl phoxim, methamidophos, pirimiphos-methyl, potassium arsenite, potassium thiocyanate, pp' -DDT, dextropropynthrin, proprene I, proprene II, proprene III, acephate, profenofos, cyfluthrin, profenofos, propfluthrin, tick, fenoxycarb, propamocarb, propoxur, Ethidathion, profenofos, hairy Deerhorn, pyrazofos, pyraflufenapyr, fenamiphos, furfluthrin, pyrethrin I, pyrethrin II, pyrethrin, pyridaben, pyridalyl, pyridaphenthion, pyrifluquinalpen, pyriproxyfen, picrorhiza, quassia, quinalphos, fenthion, rafoxanide, resmethrin, rotenone, ryanodine, octamethrin, silate, silafluoxate, silica gel, arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, suzuo, spinetoram, spinosad, spiromesifen, spirotetramat, sulfofensulfuron-sodium, flubenemide, sulfotephrofos, pyrasulfopyrad, sulfoxaflor, sulfofenthion, sulprofenofos, cyfluthrin, thiacloprid, tefurathiocarb, tebufenpyrad, pyrazofos, pyrithion I, pyrithion II, pyrithion, flubenfop, pyrithion, pyrifos, pyrithion, pyrifenozide, pyrifos, pyrifenozide, pyrifos, pyrithion, pyrifos, pyrifenozide, pyrifos, pyrifenozide, pyrifos, pyrifenozide, pyrifos, pyrifenozide, pyribenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenben, Teflubenzuron, tefluthrin, temephos, TEPP, cyfluthrin, terbufos, tetrachloroethane, fenthion, tetramethrin, transfluthrin, theta-cypermethrin, thiacloprid, thiamethoxam, secfos, bendiocarb, thiocyclam, oxalic acid thiocyclam, thiodicarb, dichlofenthion, thiosultap-disodium, thiosultap-monosodium, thuringiensis, tolfenpyrad, tetrabromthrin, transfluthrin, permethrin, fenamiphen, triazamate, triazophos, trichlorfon, isophosphophos-3, loafos, propoxyphos, pesticidal urea, methiocarb, methidathion, triazophos, XMC, methidathion, triazophos, zeta-cypermethrin, prothioconazole (zofos), and any combination thereof.

Furthermore, the compounds I of the present invention can be combined with herbicides that are compatible with the compounds I of the present invention and do not antagonize the activity of the compounds I in the medium of selective application to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal compounds I of the present disclosure may be applied in combination with one or more herbicides to control a wider range of undesirable plants. When used in combination with a herbicide, the presently claimed compounds I can be formulated with one or more herbicides, tank mixed with one or more herbicides, or applied sequentially with one or more herbicides. 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, ethametraflorine, dichlorate, metolachlor, allyl alcohol, pentachlorophenonic acid, aminazinone, ametryn, tebufenon, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, anilofos, sulflururon, asulam, atrazine, oxadiazon, tetrazolsulfuron, azifop-zine, barban, BCPC, beflubutamid, benazolin, monocarba, flumetsulam, flumeturon, bensulfuron-methyl, bensulide, bentazone, amisulam, bisphenylpyrim, bencyclazone, benzobicyclon, pyroxafen, sulfamethoxazole, norflurazone, fluroxypyr, pyriftalid, bromacil, bromoxynil, butachlor, butafenapyr, butachlor, butafenapyr-methyl benfluroxypyr, butachlor, benflurbenflurbenflurbencarb-methyl bencarb-methyl, Butafenacet, butachlor, butafenacet, buthiodazolone, buthiouron, tralkoxydim, methabenzuron, butachlor, dimethoate, cafenstrole, calcium chlorate, calcium cyanamide, crechlor ester, benfurazolin, pyraclonil, carbazole, metoclopramide, carfentrazone, CDEA, CEPC, metofen, mefenacet, butachlor, clodinafop, clonazine, clobutralin, ethoxybensulfuron, varroa, avenate, flumiclorac, clofluoren, chlorphenamine, chlorimuron, cumquat chloride, trichloropropionic acid, chlortoluron, subtilon, oxypyr, chlorpropham, chlorsulfuron, dichlorfon, bromate, indolone, cinfenofen, cinolone, cinosulfuron, pyroxsulam, dichloron, dichlorvon, len, iodiclodinyl, clodinafop-methyl, clofenpyr, clomeprop, clofenpyr, CMA, copper sulfate, clorfl, clo, CPMF, CPPC, dimethenamine, cresol, prosulfuron, cyanazine, cyhalofop-butyl, tembotrione, cyclamen, cyhalofop-methyl, cyhalofop-butyl, mequat, cyhalofop-methyl, cyprosulfan, propisochlor, triflumuron, dazomet, dichlobemide, dichlobenil, closulfuron-methyl, benzylamine, dichlorprop-p, diclosulam, licoloc, pentoxyfen, parasulfuron, diflufenil, diflufenuron, oxazalone, dimeglum, dimethenamid, isopentylon, dimethenamid, dinotefuran, trinol, penitrol, dinotefuran, penetrol, dimethenan, tebufeny, iprodione, dithiopyr, DSPA, DMEP, dimethenamid, DMPA, dimethenamid, DMEP, dimethenamid, dimethenan, sofosfate, fluxapyroxad, EPTC, imazalil, penflufen, ethalfluralin, ethametsulfuron, thiadiazolyl, benfurazar, fluroxypyr, ethoxysulfuron, nitrophenol, pyrimethabenzfen, ethoxybencarb, EXD, sulfocarb-amide, aldicacid, fenoxaprop-ethyl, isoxasulfone (fenoxasulfone), clofenoxyethanol, thiabendazole, fentrazamide, fenoxuron, ferrous sulfate, oryzalin, difloroglobin, flazasulfuron, diflufenican, fluazifop-P-butyl, isoproxypyr, fluorone-sulforon, fluazifop-butyl, flufenacet, fluthiacet-methyl, fluazifop-butyl, flufenacet-methyl, flumethazine, flumiproplopyr, flumetofen, metofen-methyl, carfenfluroxypyr, pyraflufen-ethyl, penflufen-ethyl, penetryn, fluazifop-ethyl, penfluroxypyr, penflufen-ethyl, flufen-methyl, flufenacet, penfluroxypyr, flufenacet, Tetrafluoropropionic acid, flazasulfuron, fluridone, flurtamone, fluazifop-methyl, flurtamone, metribuzin, fomesafen, fomsulfuron, glufosinate, furazafen, glufosinate, glyphosate, fluoronitrosamide, halosulfuron-methyl, flurazifop-methyl, haloxyfop-methyl, hexachloropropanone, potassium hexafluoroarsenate (hexaflurate), hexazinone, imazamox, imazapic, imazapyr, pyrazosulfuron, indanthrone, indoxachlor, ioxynil, methyl iodide, iodosulfuron, ioxynil, metribuzin, oxcarbazone, propyzadine, butamidin, isoxaflutolone, isoproturon, isoxaflutolon, isoxaclomazone, isoxaflutolone, isoxadifenoxol, isoxaflutole, isoxaflutolone, flumiclorac-methyl, benazolin, flumiclorac, clomazone, clo, Lenacil, linuron, MAA, MAMA, MCPA-thioethyl, MCPB, mechlorethac acid, metyrate, mefenacet, sulfluramid, atrazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, bispyribac-sodium, dimethenan, methabenzthiazuron, metoclopramide, imazamethabenzuron, methiocarb, methidazolin, metolachlor, methyl bromide, methyl isothiocyanate, metsulfuron, pyrosulfuron, bromuron, metolachlor, metoxuron, metribuzin, metsulfuron, metolachlor, metsulfuron, metosulfuron, metolachlor, metam, metamifop, metam, metolachlor, Dalapon, caoton, OCH, prosulfocarb, o-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, pyridaben, rimsulfuron, oxaziclomefone, oxyfluorfen, parafluorfen, paraquat, clindamycin, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, penoxsulam, pentoxazone, fomesafen, dimethenamid, nitenpyram, phenmedipham, phenthoate, picloram, pinoxaden, paraquat, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, cyclopropanil, prodiamine, flumetsulam, cyhalofop, cycloproprione, fenpropaquin, prometon, prometryn, propyzamide, propaquizachlor, propaquizafop-butyl, propyzamide, propaquizachlor, propyzamide, benbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbenbencarb, benbenbenbencarb, bencarb, propaquizamide, bencarb, benbencarb, bencarb, propaquizamide, bencarb, ben, Methisulam, prosulfocarb, prosulfuron, clomazone, butachlor, idaminon, pyraclonil, pyraflufen, pyrasulfozole, pyrazoxate, pyrazosulfuron, pyribenzoxim, pyribencarb, pyriminobac, pyrithiobac, pyriminostrobin, pyroxsulam, quinclorac, imazaquin, quizalofop-ethyl, thiocyanobenzetamide, rimsulfuron, saflufenacil, S-metolachlor, terbuthylazine, meton, mefenox, sifensulfuron, cinosulfuron, cycloxasulfuron, simazine, simetryn, SMA, sodium arsenite, sodium chlorate, sulcotrione, diclofen, metsulfuron-methyl, sulfosulfuron-methyl, sulfometuron, sulfuric acid, azapimetryn, imazachlor, triflumuron, TCA, thiuron, fursulfuron, sulfometuron, furbensulfuron, fursulfuron, furazolidone, thiuron, cufensulfuron, furazolidone, fursulam, furazolidone, and furazolidone, and furazolidone, and so, furazolin, furazolidone, furazolin, and so, Pyroxene, terbacil, tefurazone, merfennel, metoxydim, terbuthylazine, desmetryn, tefluuron, methoxyfenacet, thifluuron, thiadiazoline, thidiazuron, thiencuron-methyl, thifensulfuron-methyl, thiobensulfuron-methyl, thiobencarb, fola, penoxsulam, techolm, topramezone, triafamone, triallate, triasulfuron, tribenuron, triclopyr, imazacyclo, prodazine, trifloxysulfuron, trifluralin, triflusulfuron, trifoliate, trifluon, trifoliate, triflumuron, methimauron, methimaum and dimethenamid.

Some embodiments of the present disclosure provide methods for controlling or preventing fungal attack. The method comprises applying a fungicidally effective amount of compound I to the soil, plant, root, foliage, seed or locus of the fungus or to a locus where infestation is to be prevented. Compound I is suitable for treating banana plants at fungicidal levels while showing low phytotoxicity. Compound I may be used in the form of a protectant and/or an eradicator. One skilled in the art will appreciate that the efficacy of the compounds against the aforementioned fungi establishes the general utility of compound I as a fungicide. In particular, the compositions are effective in controlling a variety of undesirable fungi that infect banana plant crops. However, compound I has broad efficacy as a fungicide. Thus, compound I or a composition of compound I may be used in any of the methods described herein against a variety of fungi (but may or may not have selective activity against myrothecium scabrum, in the presence of any of these other fungi), including but certainly not limited to the following fungal species: anthracnose/fungal scald/crown rot/stem end rot (banana anthracnose (Colletotrichum musae)), brown spot (Cercospora hayi), Cladosporium (Cladosporium musae)), crown rot (Fusarium sp), Verticillium sp, Cladosporium sp, Acremonium sp, diamond spot (Cercospora hayi, Fusarium), Sclerotinia sclerotiorum (sclerotiniose sclerotiorum), conidiophora leaf spot (Mycosphaerella acuminata), yellow leaf spot (Mycosphaerella sclerotiorum), sheath rot (necatria, Mycosphaerella sclerotiorum), bacterial leaf spot (sclerotium sclerotiorum), bacterial leaf spot (phytophthora flavum), bacterial leaf spot (phytophthora parasitica), bacterial leaf spot (sclerotium mucor, sclerotium, rhizopus stosporum, rhizopus polyspora, rhizoctonia, bacterial leaf rot (sclerotium), bacterial leaf spot (sclerotium, phytophthora spora, rhizopus sphaera, phytophthora capsicum, rhizopus sphaera, etc. Tobacco mold (Limacenula tenuis), root rot (Rosellinia bunodes, Fusarium solani (Fusarium solani), Fusarium oxysporum (Fusarium oxysporum), Sclerotium sp., Rhizoctonia sp.), rot (Armillaria sp.), Myxoplasma saccharina (Ceratococcus paradoxa), Junghuhihonia vinata, Rhizoctonia mangifera, Staphylococcus aureus (Botr. sphaerica rivularis), Corynia elongata (Ceratococcus paradoxa), Marasmius inodorma, Pyrenophora cinerea (Phycomyces nigra), Fusarium Verticillium (Fusarium oxysporum), Mucor sp., Musca Mucor (Mucor), Mucor vulgaris (Mucor nigrum), Mucor (Mucor saprophyllum), Mucor pulus inoculus, Mucor (Mucor sp.), Mucor (Mucor sp., Mucor (Mucor), Mucor (Mucor), Rhizoctonia sp., Mucospora sp.), Marasmus sp., Mucor (Mucor), Mucor (Mucor sp.), Mucor (Mucor sp., Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), Mucor (Mucor), etc.). strain, banana), etc.).

Compound I has a wide range of efficacy as a fungicide. The exact amount of active substance applied depends not only on the particular active substance applied, but also on the particular effect desired, the fungal species to be controlled, and its growth stage, as well as the part of the plant or other product with which the compound is contacted. Thus, compound I and formulations containing the compound may not be as effective at similar concentrations or against the same fungal species.

Compound I is effective when applied to plants in a disease-inhibiting and phytologically-acceptable amount.

4.3.4. Ratio of

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

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

In some aspects, the present disclosure provides methods of controlling or preventing a fungal disease in a musa plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides a method of controlling or preventing sigatoka in plantain plantsA method, comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides methods of controlling or preventing sigatoka in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

In some aspects, the present disclosure provides a method of controlling or preventing banana bacterial wilt disease (BBW) in a plantain plant, the method comprising: bringing an area adjacent to said plant, soil suitable for supporting the growth of said plant, roots of said plant and/or leaves of said plant, withOr a tautomer or salt thereof, or a composition comprising The composition of (a).

4.3.5. Harvesting

In some aspects, the present disclosure provides methods wherein the plant species is Musa microphylla (Musa acuminata) or Musa basjoo (Musa baldisiana).

In some aspects, the present disclosure provides methods wherein the plant species is plantain.

In some aspects, the present disclosure provides methods wherein the plant species is musa basjoo.

In certain aspects, the plantain plant has fruit.

In some aspects, the present disclosure provides methods wherein the musa plant has fruit and the plant species is musa microphylla or musa basjoo.

In some aspects, the present disclosure provides methods wherein the musa plant has fruit and the plant species is musa microphylla.

In some aspects, the present disclosure provides methods wherein the musa plant has fruit and the plant species is musa basjoo.

In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of sigatoka smut reduces fruit yield by 2-95 wt%, 5-95 wt%, 10-95 wt%, 20-95 wt%, 30-95 wt%, 40-95 wt%, 50-95 wt%, 60-95 wt%, 70-95 wt%, 80-95 wt%, or 90-95 wt%. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 95-98% by weight.

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

In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 5% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 25% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of blattaria bananas reduces fruit yield by 33% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 40% by weight.

In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 50% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 66% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 75% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 80% by weight. In some aspects, the present disclosure provides methods wherein the disease or the fungal pathogen of myrothecium lanuginosus reduces fruit yield by 90% by weight.

In some aspects, the present disclosure provides methods wherein the plant fruit is plantain (plantain).

In some aspects, the present disclosure provides methods wherein the plant fruit is Cavendish banana (Cavendish banana).

In some aspects, the present disclosure provides methods wherein the plant fruit is bananas latudan (latundan banana).

Presented herein are: it will be apparent to those skilled in the art having the benefit of the teachings herein that any of the ranges or desired values set forth herein can be extended or altered without losing the effect sought.

5. Examples of the invention

The following synthetic and biological examples are provided to illustrate the techniques of the present invention and are not to be construed in any way as limiting the scope of the techniques of the present invention. All temperatures are in degrees Celsius unless otherwise noted.

These examples are provided for illustrative purposes only and are not intended to limit the scope of the present invention in any way. Efforts have been made to ensure accuracy with respect to numbers used (e.g., amounts, temperature, etc.) but some experimental error and deviation should be accounted for.

The practice of the present invention will employ, unless otherwise indicated, conventional methods of synthetic organic chemistry, protein chemistry and biochemistry and agriculture within the skill of the art. These techniques are explained fully in the literature. See, e.g., t.e. creatton, Proteins: Structures and Molecular Properties [ protein: structural and molecular properties ] (W.H. Freeman and Company [ W.H. Frahman, 1993); l.lehninger, Biochemistry [ Biochemistry ] (Worth Publishers, Inc. [ waters publishing company ], latest edition); methods In Enzymology [ Methods In Enzymology ] (s.colwick and n.kaplan eds., Academic Press, Inc. [ Academic Press corporation ]); remington's Agricultural Sciences, 18 th edition (Easton, Pennsylvania: Mack Publishing Company, 1990); carey and Sundberg Advanced Organic Chemistry, 3 rd edition (Plenum Press, Proben Press), volumes A and B (1992) and Organic Reactions, volumes 1-40 (John Willi-father publishing Co., 1991).

The present technology is further understood by reference to the following examples, which are intended to be purely exemplary of the present technology. The present technology is not to be limited in scope by the illustrative embodiments, which are intended as illustrations of individual aspects of the present technology. Any functionally equivalent method is within the scope of the present technology. Various modifications of the present technology, in addition to those described herein, will be apparent to those skilled in the art from the foregoing description and accompanying drawings. Such modifications are intended to fall within the scope of the appended claims.

5.1. Example 1: in situ use

On-site assessment for banana black streak leaf spot pathogen

Test 1: compound I was synthesized according to methods known in the art, and test samples were obtained and formulated. Fungicidal treatment agents (fungical treatment) containing 25, 50, 75, 100, 150, 200 and 250g of compound I10% EC (GF-3645) and 40% v/v (adjuvant/control agent) adjuvant 50% Plurafac LF1300EC were applied to determine the efficacy on banana black leaf spot caused by banana black streak pathogen. When 40% v/v (adjuvant/control) of 50% Plurafac LF1300EC adjuvant was applied, the commercial competitive levels of compound I were higher for 150, 200 and 250g ai/ha and control of banana black leaf spot disease was achieved. The results are from field test TAFS17F05, archived in HARMONY under protocol number PA17X 02016.

Test TAFS17F05 was designed with RCB and repeated 4 times. The test was carried out by manual inoculation and received two applications at 800L/ha intervals of 10 days.

Test TAFS17F05, 2 day protectant (boxplot)

Test 2: compound I was synthesized according to methods known in the art, and test samples were obtained and formulated. The DHP compound I (GF-3645) 10% EC controls the banana black leaf spot caused by the banana black stripe virus on banana crops. Two single-leaf trials in the costa rica pica in 2017 from month 5 to month 7 showed that compound I had strong kill at 50, 100, 150 and 200g ai/haFungal activity to control black leaf spot on bananas. Compared to the commercial standard for disease control of sigatoka in banana crops, fungicide compound I, even applied at 100g ai/ha, was found to bePrevention ofAnd also show excellent results in terms of therapeutic effects. Four ratios of compound I10% EC (GF-3645) (50, 100, 150 and 200g ai/Ha) were mixed with mineral oil (7L/Ha) and tested to determine efficacy on banana black leaf spot. A100 g ai/ha treatment was tested with water to observe the oil contribution. In the treatment ofAnd preventive effectsIn aspect, the effectiveness of compound I at 100g ai/Ha is similar or better than the main therapeutic commercial standard difenoconazole (Sico 25 EC). Mixing with oil shows better performance than mixing with water. The results are from field tests ACF1718A and ACF1718B, filed in HARMONY, protocol No. LA17X 02050.

Test ACF1718A and ACF1718B were designed with RCB and repeated 5 times. These tests were carried out under a single leaf test method, applied once on leaves No. 1 (test for preventive effect) and leaves No. 3 (test for therapeutic effect), at a rate of 23L/ha.

Summary of two tests with respect to ACF1718A and ACF1718B, 30 days after application (boxplot)

Average comparison: tukey's HSD test 0, 05.