Picolinamides as fungicides

Abstract

To provide an efficient method for producing a compound that is an intermediate of picolinamide used as fungicides.SOLUTION: The present invention provides a method for preparing a compound of formula 3.2 as described by the following scheme, where R1 denotes hydrogen or alkyl; R2 denotes methyl; R3 denotes aryl or saturated cyclic carbon chain; and R10 denotes hydrogen or alkyl.SELECTED DRAWING: None

Description

Technical Field

[0001] Cross - Reference to Related Applications This application claims the benefit of U.S. Provisional Patent Application No. 62 / 640,424, filed on Mar. 8, 2018, and U.S. Provisional Patent Application No. 62 / 640,434, filed on Mar. 8, 2018, and the disclosures of those applications are hereby incorporated by reference in their entireties.

Background Art

[0002] Fungicides are natural or synthetic - derived compounds that act to protect and / or treat plants against damage caused by agriculturally - relevant fungi. Generally, there is no single fungicide that is useful in all situations. Therefore, research is ongoing to produce fungicides that can have good performance, be easy to use, and be of low cost.

Summary of the Invention

Means for Solving the Problems

[0003] The present disclosure relates to picolinamides and their use as fungicides. The compounds of the present disclosure can provide protection against Ascomycetes, Basidiomycetes, Deuteromycetes, and Oomycetes.

[0004] One embodiment of the present disclosure is Formula I:

Chemical Formula

Chemical Formula

[0005] Another embodiment of the present disclosure may include a fungicidal composition for controlling or preventing fungal attack, comprising the compound described above and a botanically acceptable carrier material and].

[0006] Yet another embodiment of the present disclosure is a method for controlling or preventing fungal attack on a plant comprising applying a fungicidally effective amount of one or more of the compounds described above to at least one fungus, plant and the area adjacent to the plant

[0007] The following terms can include common "R" groups within the scope of their definitions. For example, the statement "the term alkoxy refers to an -OR substituent" will be understood by those skilled in the art It will also be understood that these "R" groups are included for illustrative purposes and should not be considered as limiting the substitutions for formula I or being limited by the substitutions for formula I within the scope of the definitions of the following terms

[0008] The term "alkyl" refers to a branched, unbranched, or saturated cyclic carbon chain such as, but not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl cyclohexyl, etc

[0009] The term "alkenyl" refers to, but is not limited to, ethenyl, propenyl, butenyl, isopropenyl, isobutenyl cyclobutenyl, cyclopentenyl, cyclohexenyl, etc A branched, unbranched, or cyclic carbon chain containing one or more double bonds, which is not limited thereto refers to.

[0010] The terms "aryl" and "Ar" refer to a single ring or bicyclic of any aromatic ring containing 0 heteroatoms which is monocyclic or bicyclic.

[0011] The term "heterocyclyl" refers to a monocyclic or bicyclic of any aromatic or non-aromatic ring containing one or more heteroatoms which is monocyclic or bicyclic.

[0012] The term "alkoxy" refers to an -OR substituent.

[0013] The term "acyloxy" refers to an -OC(O)R substituent.

[0014] The term "cyano" refers to a -C≡N substituent.

[0015] The term "hydroxyl" refers to an -OH substituent.

[0016] The term "amino" refers to an -N(R) 2 substituent.

[0017] The term "arylalkoxy" refers to -O(CH 2 ) n Ar [wherein n is an integer selected from the list of 1, 2, 3, 4 , 5, or 6].

[0018] The term "haloalkoxy" refers to an -OR-X substituent where X is Cl, F, Br, or I, or any combination thereof .

[0019] The term "haloalkyl" refers to an alkyl substituted with Cl, F, I, or Br, or any combination thereof .

[0020] The term "halogen" or "halo" refers to one or more halogen atoms defined as F, Cl, Br, and I.

[0021] The term "nitro" refers to the -NO 2 substituent.

[0022] The term thioalkyl refers to the -SR substituent.

[0023] Throughout the disclosure, references to compounds of formula I are to be read as including all of their stereoisomers, e.g., diastereomers, enantiomers, and mixtures thereof. In another embodiment, formula (I) is to be read as including its salts and hydrates. Exemplary salts include, but are not limited to, hydrochloride, hydrobromide, hydroiodide, trifluoroacetate, and trifluoromethanesulfonate.

[0024] It is also understood by those skilled in the art that further substitutions may be allowed as long as the laws of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity, unless otherwise indicated.

[0025] Another embodiment of the disclosure is the use of a compound of formula I for protecting a plant from attack by phytopathogenic organisms or for treating a plant in which phytopathogenic organisms are present, which comprises applying the compound of formula I or a composition comprising the compound to the soil, a plant, a part of a plant, a leaf, and / or a root.

[0026] In addition, another embodiment of the disclosure is a composition useful for protecting a plant from attack by phytopathogenic organisms and / or for treating a plant in which phytopathogenic organisms have occurred, which comprises a compound of formula I and a botanically acceptable carrier material. ​​

Mode for Carrying Out the Invention

[0027] The compounds of the present disclosure can be administered by any of a variety of known techniques, either as the compounds or in formulations containing the compounds. For example, the compounds can be applied to the roots or leaves of plants for the control of a variety of fungi without impairing the commercial value of the plants. The materials can be administered in any of the commonly used formulation types, such as solutions, powders, wettable powders, flowables, or emulsions. Preferably, the compounds of the present disclosure are administered in the form of a formulation containing one or more compounds of Formula I together with a botanically acceptable carrier. The concentrated formulation can be dispersed in water or other liquid for application, or the formulation is in powder or granular form and can then be applied without further treatment. The formulations can be prepared according to procedures conventional in the pesticide art.

[0028]

[0029] The present disclosure contemplates all vehicles for which one or more compounds can be formulated for delivery and use as fungicides. Typically, the formulations are administered as aqueous suspensions or emulsions. Such suspensions or emulsions can be prepared from solids known commonly as wettable powders, which are water-soluble, water-suspendable or emulsifiable formulations, or from liquids known commonly as emulsions, aqueous suspensions or suspension concentrates (SCs). As will be readily understood, any material can be used to which these compounds can be added as long as the desired utility is achieved without significantly interfering with the antifungal activity of these compounds.

[0030] The wettable powder that can be compressed to form a water-solubilized granule contains a close mixture of one or more compounds of formula I, an inert carrier, and a surfactant. The concentration of the compound in the wettable powder can be about 10% to about 90% by weight, more preferably about 25% to about 75% based on the total weight of the wettable powder. In the preparation of the wettable powder formulation, the compound may be blended with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsifier that can be advantageously used herein can be readily determined by those skilled in the art and includes various nonionic, anionic, cationic, and amphoteric emulsifiers or a combination of two or more emulsifiers. In the preparation of the wettable powder formulation, the compound is blended with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized. In the preparation of the wettable powder formulation, the compound is blended with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized. In the preparation of the wettable powder formulation, the compound is blended with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized. In the preparation of the wettable powder formulation, the compound is blended with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized. In such an operation, the fine carrier and the surfactant are typically blended with the compound and pulverized.

[0031] The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used. The emulsion of the compound of formula I may contain a convenient concentration of the compound, such as about 1% to about 50% by weight based on the total weight of the emulsion, in a suitable liquid. The compound may be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can 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 hydrocarbons of petroleum such as heavy aromatic naphtha, especially high-boiling naphthalenes and olefinic moieties. Other organic solvents such as terpene solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol can also be used.

[0032] The emulsifier that can be advantageously used herein can be readily determined by those skilled in the art and includes various nonionic, anionic, cationic, and amphoteric emulsifiers or a combination of two or more emulsifiers. The emulsifier that can be advantageously used herein can be readily determined by those skilled in the art and includes various nonionic, anionic, cationic, and amphoteric emulsifiers or a combination of two or more emulsifiers. Examples of nonionic emulsifiers useful in the preparation of emulsions include blends of surfactants. Poly alkylene glycol ethers, alkyl and aryl phenols, aliphatic alcohols, condensates of aliphatic amines or fatty acids with ethylene oxide, ethoxylated alkylpheno ls such as propylene oxide, and carboxylic acid esters solubilized with polyols or polyoxyalkylene are mentioned. Examples of cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Examples of anionic emulsifiers include oil-soluble salts of alkylaryl sulfonic acids (e.g., calcium), oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphorylated polyglycol ethers.

[0033] Representative organic liquids that can be used in the preparation of emulsions of the compounds of the present disclosure are aromatic liquids such as xylene, propyl benzene fraction; or substituted aromatic organic liquids such as mixed naphthalene fraction, mineral oil, dioctyl phthalate ; kerosene; various fatty acid dialkylamides such as n-butyl ether of diethylene glycol, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, especially dimethylamide of fatty glycol and glycol derivatives, mineral oil, aromatic solvents, petroleum fractions or hydrocarbons such as paraffin oil; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, camellia oil; esters of the above vegetable oils and the like. Mixtures of two or more organic liquids may be used in the preparation of emulsions. Examples of organic liquids include xylene and propylbenzene fraction, and in some cases xylene is most preferred. The surface-active dispersant is typically used in liquid formulations and is used in an amount of 0.1 to 20 weight percent, based on the combined weight of the dispersant and one or more compounds. The formulations can also contain other compatible additives, such as plant growth regulators and other biologically active compounds used in agriculture. The aqueous suspension contains a suspension of one or more water-insoluble compounds of formula I dispersed in an aqueous vehicle at a concentration in the range of about 1 to about 50 weight percent, based on the total weight of the aqueous suspension. The suspension is prepared by finely grinding one or more compounds and vigorously mixing the ground material with a vehicle composed of water and a surfactant selected from the same types as those considered above.

[0034] Other components, such as inorganic salts and synthetic or natural rubbers, can also be added to increase the density and viscosity of the aqueous vehicle. The compounds of formula I can also be applied as a granule formulation, which is particularly useful for application to the soil. The granule formulation generally contains about 0.5 to about 10 weight percent of the compound, based on the total weight of the granule formulation, dispersed in an inert carrier composed entirely or mostly of a coarsely divided inert material such as attapulgite, bentonite, diatomaceous earth, clay, or similar inexpensive substances. Such formulations are usually prepared by dissolving the compound in a suitable solvent and applying it to a preformed granular carrier having an appropriate particle size in the range of about 0.5 to about 3 mm. A suitable solvent is one in which the compound is substantially or completely soluble. Such formulations can also be prepared by making a paste or paste of the carrier, compound, and solvent, crushing it, and drying it to obtain the desired granular particles.

[0035] The compounds of formula I can also be applied as a granule formulation, which is particularly useful for application to the soil. The granule formulation generally contains about 0.5 to about 10 weight percent of the compound, based on the total weight of the granule formulation, dispersed in an inert carrier composed entirely or mostly of a coarsely divided inert material such as attapulgite, bentonite, diatomaceous earth, clay, or similar inexpensive substances. Such formulations are usually prepared by dissolving the compound in a suitable solvent and applying it to a preformed granular carrier having an appropriate particle size in the range of about 0.5 to about 3 mm. A suitable solvent is one in which the compound is substantially or completely soluble. Such formulations can also be prepared by making a paste or paste of the carrier, compound, and solvent, crushing it, and drying it to obtain the desired granular particles.

[0036] The powder containing the compound of formula I is prepared by intimately mixing one or more compounds in powder form with a suitable powdered agricultural carrier such as kaolin clay, ground volcanic rock, etc. It can be done. The powder can preferably contain about 1 to about 10 weight percent of the compound based on the total weight of the powder.

[0037] The formulation can additionally contain a co-surfactant to enhance the adhesion, wetting, and penetration of the compound to the target crop or organism. These co-surfactants can be optionally used as components of the formulation or as a tank mix. The amount of the co-surfactant typically varies from 0.01 to 1.0 volume percent, preferably 0.0 5 to 0.5 volume percent, based on the amount of water sprayed. Suitable co-surfactants include ethoxylated nonyl phenol, ethoxylated synthetic or natural alcohols, salts of sulfosuccinic acid esters, ethoxylated organic silicones, ethoxylated fatty amines, blends of surfactants and mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)); nonylphenol ethoxylate chelates; benzyl cocalkyl dimethyl quaternary ammonium salts; blends of petroleum hydrocarbons, alkyl esters, organic acids, and anionic surfactants; C ~C alkyl polygly ucosides; phosphorylated alcohol ethoxylates; natural primary alcohols (C ~C 9 ~C 11 alkylene block copolymers; poly siloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methyl 12 ~C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymer; poly siloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methyl Hydrogenated seed oil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99 are mentioned, but are not limited thereto. The formulations may include oil-in-water emulsions such as those disclosed in U.S. Patent Application No. 11 / 495,228, which disclosure is incorporated herein by reference. The formulations may optionally include combinations containing other pesticidal compounds. Such additional pesticidal compounds are compatible with the compounds of the present disclosure in the medium selected for application and are fungicides, insecticides, herbicides, nematicides, acaricides, arthropod repellents, bactericides, or combinations thereof that do not antagonize the activity of the compounds of the present invention. Thus, in such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. The compounds of the present disclosure may be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied together with one or more other fungicides to control a variety of undesirable diseases. When used with other fungicides, the compounds claimed in the present invention can be formulated with other fungicides, tank-mixed with other fungicides or applied subsequent to other fungicides. Such other fungicides include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenyl

[0038] The formulations may optionally include combinations containing other pesticidal compounds. Such additional pesticidal compounds are compatible with the compounds of the present disclosure in the medium selected for application and are fungicides, insecticides, herbicides, nematicides, acaricides, arthropod repellents, bactericides, or combinations thereof that do not antagonize the activity of the compounds of the present invention. Thus, in such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. acaricides, arthropod repellents, bactericides, or combinations thereof that do not antagonize the activity of the compounds of the present invention. Thus, in such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. acaricides, arthropod repellents, bactericides, or combinations thereof that do not antagonize the activity of the compounds of the present invention. Thus, in such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. In such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. In such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1. In such embodiments, the other pesticidal compounds are used as supplementary poisons in the same or different pesticidal applications. The compounds of formula I and the pesticidal compounds in the combination can generally be present in a weight ratio of 1:100 to 100:1.

[0039] The compounds of the present disclosure may be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied together with one or more other fungicides to control a variety of undesirable diseases. When used with other fungicides, the compounds claimed in the present invention can be formulated with other fungicides, tank-mixed with other fungicides or applied subsequent to other fungicides. Such other The compounds of the present disclosure may be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied together with one or more other fungicides to control a variety of undesirable diseases. When used with other fungicides, the compounds claimed in the present invention can be formulated with other fungicides, tank-mixed with other fungicides or applied subsequent to other fungicides. Such other The compounds of the present disclosure may be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied together with one or more other fungicides to control a variety of undesirable diseases. When used with other fungicides, the compounds claimed in the present invention can be formulated with other fungicides, tank-mixed with other fungicides or applied subsequent to other fungicides. Such other fungicides include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenyl The compounds of the present disclosure may be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied together with one or more other fungicides to control a variety of undesirable diseases. When used with other fungicides, the compounds claimed in the present invention can be formulated with other fungicides, tank-mixed with other fungicides or applied subsequent to other fungicides. Such other fungicides include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenyl ​Phenol, 8-Hydroxyquinoline Sulfate, Ametoctradin, Aminopyrifen n, Amisulbrom, Antimycin, Ampelomyces quisqualis ), Azaconazole, Bacillus subtilis ), Bacillus subtilis strain QST713, Benalaxyl, Benomyl, Benfuracarb Isopropyl l, Benzobindiflu pyr, Benzylaminobenzenesulfonic Acid (BABS) Salt, Bicarbonate Salt, Biphenyl, Bismuthiazole, Bitertanol, Bixafen, Blasticidin-S , Borax, Bordeaux Mixture, Boscalid, Bromoconazole, Buprimate, Calcium Polysulfide , Captan, Captan, Carbendazim, Carboxin, Capropamid , Carboxylic, Chlazafenone, Chloroneb, Chlorothalonil , Chlorothalonil, 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, Dicromet, Dichloran, Diethofencarb, Difenoconazole , Difenzoquat Ion, Diflumezopyrim, Dimethomorph, Dimoxystrobin , Diniconazole, Diniconazole-M, Dinobuton, Dinocap, Diphenylamine , Dithianon, Dodemorph, Dodemorph Acetate, Dodine, Dodine Free Base, Edifenphos Azoxystrobin, azoxastrobin, epoxyconazole, ethaboxam, ethoxyquin , etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole , fenfluram, fenhexamid, phenoxanil, fenpiclonil, fenpropidin , fenpropimorph, fenpyrazamine, fenbutatin oxide, fenbutatin acetate, hydroxyfenbutatin oxide, ferbam, ferimzone, fluazinam, fluoxastrobin, fluopicolide , fluopyram, fluoroimide, fluoxapiprolin, fluoxastrobin, flutriafol , flusilazole, flusulfamide, fluthianil, flutolanil, flutriafol, fluoxapiroxad , hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine , iminoctadine triacetate, iminoctadine tris(albesilate), ipfencarbazone , iprobenfos, iprodione, iprovalicarb, isofetamid, isoflucypram , isoprothiolane, isopyrazam, isothianil, kasugamycin, kasugamycin hydrochloride hydrate , kresoxim-methyl, lime sulfur, mancopper, mancozeb, mandipropamid , maneb, mefenoxam, mepanipyrim, mepronil, meptyldinocap , metalaxyl, metalaxyl-M, metconazole, metiram, metominostrobin , metrafenone, metsulfovax, myclobutanil, nabam, nuarimol , octhilinone, oxadixyl, oxolinic acid, oxycarboxin, paclobutrazol , penconazole, pencycuron, penthiopyrad, permethrin, picoxystrobin , prochloraz, procymidone, propamocarb, propamocarb hydrochloride dinocap), mercuric chloride, mercuric oxide, mercury chloride, metalaxyl, metalaxyl-M, metam, metammonium, metakali, metasodium, metconazole, metam-sulphocarbu, methyl iodide, methyl isothiocyanate, methyram, metominostrobin, metrafenone, mildeomycin, microbutanyl, nabam, nitrotal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acid), orysastrobin, oxadixyl, oxathiapiprolin, copper oxine, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenol laurate, penthiopyrad, phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxin, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pidiflumetofen, pyraclostrobin, pyraoxystrobin, pyraclostrobin, pyrazoflumid, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyrifluophenone, pyroquilon, quinclamin, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiopham,simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tall oil, tebuconazole, tebufloquin, tecnazene, tetraconazole -M, metam, metammonium, metakali, metasodium, metconazole -ole, methyl isothiocyanate, methyram, metominostrobin -strobin, metrafenone, mildeomycin, microbutanyl, nabam, nitrotal-isopropyl -mol, octhilinone, ofurace, oleic acid (fatty acid), orysastrobin -dixyl, oxathiapiprolin, copper oxine, oxpoconazole fumarate, oxycarboxin -zoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenol laurate -pyrad, phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin -strobin, polyoxin B, polyoxin, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate -azole, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid -azole, prothioconazole, pidiflumetofen, pyraclostrobin, pyraoxystrobin, pyraclostrobin -azole, propineb, proquinazid, prothioconazole, pidiflumetofen, pyraclostrobin -fen, pyraclostrobin, pyraoxystrobin, pyraclostrobin, pyrazoflumid -azole, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyrifluophenone -one, quinclamin, quinoxyfen, quintozene, Reynoutria sachalinensis extract Reynoutria sachalinensis extract -xane, silthiopham, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate -oxide, spiroxamine, sulfur, SYP-Z048, tall oil, tebuconazole, tebufloquin -azole, tebufloquin, tecnazene, tetraconazole Zole, thiabendazole, diflumetorim, thiophanate-methyl, thiram, thiazinyl , tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, tria zoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole , triphorine, triticonazole, validamycin, valifenalate, valiphenal , vinclozolin, dinneb, ziram, zoxamide, Candida oleophila , Fusarium oxysporum , Gliocladium species, Phlebiopsis gigantea , Streptomyces griseoviridis , Trichoderma species, (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-dithi-in 1,1,4 ,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chl oride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methyl rhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanate, ampro pylfos, anilazine, azitiram, barium polysulfide, Bayer 32394 ​, benodanil, benquinox, bentazone, benzamacril; benzamacril isobutyl 、benzamorph, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate 、carbamorph, CECA, chlobenil, chloraniformethan, chlorphenazole 、chlorquinaldol, copper bis(3-phenylsalicylate), copper zinc chromate, cymoxanil 、cyprodinil, cyprofuram, decafentin, dichlobentiazox, dichloran 、dichlorozolin, dichlobutrazol, dimethirimol, dinocap, dinosulfon 、dinoterbon, diphenylamine, dipyrithione, ditalone, dodicin 、drazoxolon, EBP, enoxastrobin, ESBP, etaconazole, etem 、ethirim, fenaminostrobin, fenaminosulf, fenapanil, fenitrothion 、fenpicoxamid, flupicoxamid, flufenoxystrobin, fluopyram, flutriafol 、flucarbanil, fluconazole, fluconazole-cis, flumecyclox, flutolanil 、gliocladin, gliovirin, halacrinate, Hercule s 3944, hexythiazox 、ICIA0858, ipfentrifluconazole, 、hexythiophos, ICIA0858, ipfentrifluconazole,​​​​​ Epifulphenokin, isopamphos, isovalidione, mandestrobin, mebenyl, mecarbinzid, mefenoxazol ole, mepronil, meptyldinocap, metalaxyl, metconazole, metazoxolone, metofluthram, methylmercury dicyandiamide, metosulam rubox, methyltetraprole, milneb, mucobromic anhydride, microzolin, N-3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide , natamycin, N-ethylmercury-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate , phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyrapropion, pyridachlometyl, pyridinonitrile, pyrisolaxazole, pyroxychlor , pyriproxyfen, quinacetol; quinacetol sulfate, quinazamide, quinine, quinoferin, rabenzazole, salicylanilide, SSF-109, sultropen , tecloftalam, thiadifluor, thiophene, thiochlorfenphim, thiophanate, thiocinox, thioxymide, triamiphos, triarimol , triazbutyl, triclamide, triclopyricarb, triflumizopyrim, urbacid, zarilamide, and any combination thereof can be mentioned. In addition, the compounds described herein are combined with other pesticidal agents including insecticides, nematicides, acaricides, arthropod repellents, fungicides, or combinations thereof that are compatible with the disclosed compounds in a medium selected for application and do not antagonize the activity of the compounds of the present invention.

[0040] ​​​​​​​​​ Combined, pesticidal mixtures and synergistic mixtures thereof can be formed. The present disclosure The fungicidal compounds of can be applied together with one or more other pesticidal agents to control a variety of undesirable pests. When used with other pesticidal agents, the compounds claimed in the present invention can be formulated with other pesticidal agents, tank mixed with other pesticidal agents or applied subsequent to other pesticidal agents. Typical pesticidal agents include 1,2-dichloropropane, abamectin, acephate, acetamiprid, ace thion, acetoprole, acrinathrin, acrylonitrile, acinonapyr, aphid pyropene, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin, alosamidin, alicarb, alpha-cypermethrin, alpha-ecdysone, a lpha-endosulfan, amidithion, aminocarb, amiton, amiton oxalate ate, amitraz, anabasine, atidathion, azadirachtin, azamethiphos, azin phosethyl, azinphosmethyl, azothoate, barium hexafluorosilicate, balt rin, benfuracarb, benfuracarb, bensultap, benzpyrimoxan, beta -cyfluthrin, beta-cypermethrin, bifenthrin, bioallethrin, bioetha nomethrin, bioresmethrin, bistrifluron, borax, boric acid, broflanilide, bromfenvinphos, bromocyclene, bromo -DDT, bromophos, bromophosethyl, bufencarb, buprofezin, butacarb b, butathiophos, butoxycarboxime, butonate, butoxycar b, butathiophos, butoxycarboxime, butonate, butoxycar Boxim, Kazusa Phosphorus, Calcium Arsenate, Calcium Polysulfide, Camphechlor, Carbano Rate, Carbaryl, Carbofuran, Carbon Disulfide, Carbon Tetrachloride, Carbophenothion, Ca rbosulfan, Cartap, Cartap Hydrochloride, Chlorantraniliprole, Chlorpyrifos Cyclen, Chlordane, Chlordecone, Chlordimeform, Chlordimeform Hydrochloride, Ch lorpyrifos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Ch lormephos, Chloroform, Chloropicrin, Chlorprothrin, Chloroxime, Ch lorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Chlorantraniliprole, Chlorpyrifos, Chlorpyrifos Methyl, Chlorothiophos, Chromafenozide, Cinerin I, Cinerin II, Cinerins, Cis-methrin, Cloethocarb, Clozapam Ace, Dimetrin, Dimethylvinphos, Dimethilan, Dinex, Dinex-Diclex Diclexine, Dinoprop, Dinocap, Dinotefuran, Diphenolan , Dioxabenzophos, Dioxacarb, Dioxathion, Disulfoton, Dichlorvos , d-Limonene, DNOC, DNOC-Ammonium, DNOC-Potassium, DNOC- Sodium, Doramectin, Ecdysterone, Emamectin, Emamectin Benzoate, EMPC, Empenthrin, Endosulfan, Endothion, Endrin, EPN, E Pofenonan, Eprinomectin, Epsilon-Methofluthrin, Epsilon-Monfluthrin Orotriene, Esdepallethrine, Esfenvalerate -ate, Ethaphos, Ethiprole, Ethoprophos, Ethyl Formate, Ethyl-DDD, Ethylene Dibromide, Ethylene Dichloride, Ethylene Oxide , Ethofenprox, Etrimfos, EXD, Famphur, Fenamiphos, F enazaflor, Fenchlorphos, Fenethacarb, Fenfluthrin, Fenitrothion , Phenobucarb, Phenoxacrim, Phenoxycarb, Fenpyrethrin (fen pirithrin), Fenpropathrin, Fensulfothion, Fenthion, F enthion Ethyl, Fenvalerate, Fipronil, Flometoquin, Flonicamid, Flu azaindolizine, Flubendiamide, Flucofuron, Flucycloxuron, Flucythrinate , Fluensulfone, Flufenirim, Flufenoxuron, Flufenprox , Flufiprole, Flufexahone, Flupyradifurone, (flufenprox), Flufiprole, Flufexahone, Flupyradifurone, Full pyrimidine, full valinate, full xametamide, honophosph, formetanate, form tanate hydrochloride, formothion, formparanate, formparanate hydrochloride, meth yl lan, phosphirate, phosphithiane, flaticarb, fletrin, gamma-cyhalo thrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD, hept achlor, heptafluthrin, heptenophos, heterophos, hexaflumuron, HHDN , hydramethylnon, hydrogen cyanide, hydroprene, hikindarb, imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isazophos, isobenzan , isocarboxophos, isocycloseram, isodrin, isofenphos, isofenphos methyl, isoprocarb, isoprothiolane, isothioate, isoxathion, iverm ectin, jasmonin I, jasmonin II, jodfenphos (jodfenpho s), juvenile hormone I, juvenile hormone II, juvenile hormone III, kappa-bifenthrin , kappa-tefluthrin, kerevan, kinoprene, lambda-cyhalothrin, lead arsenate, lep imectin, leptophos, lindane, lirimfos, lufenuron, lithidathion, malath ion, malonoben, majidox, mecarbam, mecarphon, menazon, meperfluthrin , mephospholan, mercurous chloride, mesulfenphos, metaflumizone, methacrifos, methamidophos, methidathion, methiocarb, methocrotophos, methomyl, methoprene, methoxychlor, methoxyphenozide, methyl bromide, methyl isothiocyanate, methyl ch lorofom, methylene chloride, metofluthrin, metolcarb, methoxadiazone, mevin phos, mexacarbate, milbemectin, milbemycin oxime, mipafox, m Irex, molosultap, monofluorothrin, monocrotophos Trichlorfon, monomehypo, monosultap, morphothion, moxidectin Dectomax, naphthalophos, naled, naphthalene, nicotine, nifluridide, nitenpyram M, nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl Oxydemeton-methyl, oxydeprofos, oxydisulfoton, para-dichlorobenzene, parathion Parathion-methyl, penfluron, pentachlorophenol, permethrin, fencaptan, phenothrin Phenthoate, phorate, phosalone, phosphorane, phosmet, phosnichlor Phosphamidon, phosphine, hokxim, hokxim-methyl, pirimiphos-methyl, pirimicarb Pirimiphos-ethyl, potassium arsenite, potassium thiocyanate, p,p'-DDT, prallethrin Precocene I, Precocene II, Precocene III, primidophos, profenofos, profluralin Promacyl, promecarb, propaphos, propetamphos, propoxur, prothidathion Prothiofos, protoparathion, pyrethroids, pyridaben, pyridalyl, pyridafenthion Pyrifluquinazon, pyrimidifen, pyriminostrobin, pyrimitate, pyriprole, pyriproxyfen Quinalphos, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone Ryania, sabadilla, schradan ​​​Selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sofamid, spinetram, spi nosad, spirodiclofen, spiroxamine, spirotetramat, sulfoxaflor, sulco flon sodium, sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, tau-fluvalinate, tazimcarb, TDE, tebufenozide, te bufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEP P, terallethrin, terbufos, tetrachlorantraniliprole, tetrachloroethane , tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole , theta-cypermethrin, thiacloprid, thiamethoxam, chlorpyrifos, thiocarb oxime, thicyclam, thicyclam oxalate, thiodicarb, thiafenthoxam, omethoate, thiosultap, thiosultap disodium, thiosultap monosodium , tsingyensine, thioxazafen, tolfenpyrad, tralomethrin, tran sfluthrin, transfluthrin, triarathene, triazamate, triazophos, trichlorfon, trichlorometaphos-3, trichloronat (trichloronat), triphenylphosphate, triflumizole, triflumuron, trimethacarb, triprene , chlorpyrazoflor, bamidothion, vaniliprole, XMC, xylylcarb, ze -ta-cypermethrin, zolaprofos, and any combination thereof, but not limited thereto.

[0041] In addition, the compounds described herein are present in a medium selected for application in combination with a herbicide that is compatible with the disclosed compounds and does not antagonize the activity of the compounds of the present invention and may form a pesticidal mixture and its synergistic mixture. The fungicidal compounds of the present disclosure for controlling a variety of undesirable plants, may be applied together with one or more other herbicides if. When used with a herbicide, the compounds claimed by the present invention can be formulated with the herbicide or tank-mixed with the herbicide, or applied subsequently to the herbicide. Typical herbicides include 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, asifluorfen, a clonifen, acrolein, alachlor, aridichlor, alloxydim, allyl alcohol -ol, allolact, ametrydione, ametryn, amibuzin, amicarbazone, amide sulfuron, aminocyclopyrachlor, aminopyralid, amiprophos-methyl, amitrole -ol, ammonium sulfamate, anilofos, anisuron, asulam, atraton , atrazine, azafenidin, azimsulfuron, aziprotrin, barban, BCP C, beflubutamid, beflubutamid-M, benazolin, bencarbazone, benfluralin -n, benfuresate, bensulfuron, bensulide, bentazone, benzadox, benz fendizone, benziprogram, benzobicyclon, benzofenap, benzofluoro, benzoylprop, benzothiazuron, bicyclopyrone, biphenox, bilanaphos and bispyribac, bixlozone, borax, bromacil, bromobonyl, bromobutide, bromophenoxime, bromoxynil, bromopyrazone, butachlor, butaphenacyl, Butamiphos, butachlor, buthidazole, buturon, butralin, butroxydim, buturon, butylate, cacodylic acid, cafestrol, calcium chlorate, calci um cyanamide, camvbenzchlor, carbasulam, carbethamid, carboxazole, clo ropurocarb, carfentrazone, CDEA, CEPC, chromomethoxyphen, chloro lamben, chloranocryl, clodinafop, clomazone, chlorbromuron, chlorbu fam, chlorflurecol, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlormuron, chloronitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorosulfu ron, chlorothalonil, chlorothiamide, cinidon-ethyl, cinmethylin, cinosulfuron, cis-anilide, clathrifos, clethodim, cliodinate, clodinafop (clofop), clomazone, clomeprop, cloprothr op, clopyralid, chloransulam, CMA, copper sulfate, CPMF, CPPC, credazine, cre zol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyranil, cy clopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop -butyl, cyperquat, cyprazine, cyproconazole, cyprodinil, dimefuron, dalapon, da zomet, deltachlor, desmedipham, desmethrin, diazinon, dicamba, dichlo rophen, dichloral urea, dichlormate, dichlorprop, dichlorprop-P, dichlofop, dichlorsulam, diethamquat, diethyl, diphenpen tene, Difenoxuron, Difenzoquat, Diflumetican, Diflufenopyr, Dime thyl, Dimethipin, Dimethachlor, Dimethametryn, Dimethenamid, Dimethena mid-P, Dimexano, Dimidazon, Dinotramine, Dinofenate, Dinoprop, Di nosam, Dinoseb, Dinoterb, Difenamide, Dipropetryn, Diquat, Disul fur, Dithiolpyr, Diuron, DMPA, DNOC, DSMA, EBEP, Eglinazine, E ndothal, Epronaz, EPTC, Erbon, Esprocarb, Etalfluralin, E thametsulfuron, Ethidimuron, Ethiolate, Ethofumesate, Ethoxyphen, E thoxysulfuron, Ethinofen, Ethiproid, Ethobenzanid, EXD, Fenathr am, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxasulfu ron, Fenquinotrione, Fenteraool, Fenthiaprop, Fentrazamide , Fenuron, Ferrous sulfate, Flamprop, Flamprop-M, Flazasulfuron, Florasulam, Flupirauxifen, Fluaazifop, Fluaazifop-P, Flu azolate, Flucarbazone, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenican, Flufenpyr, Flumetsulam, Flumethiamide, Flumiclorac, Flu mioxazin, Flumipropin, Fluometuron, Fluorodifen, Fluoroglycof en, Fluoromidine, Fluoronitrofen, Fluothiuron, Flupoxam, Flup ropacil, Flupropanate, Flupyrsulfuron, Fluridone, Flurochloridone, F luroxypyr, Flurtamon, Fluthiacet, Homethiofen, Horamsulfuron, Hos amine, Furyloxyfen, Glufosinate, Glufosinate-P, Glyphosate, Ha Roxifene, halosafen, halosulfuron, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, ioxynil, ipazine, ipfencarbazone, iprocarb, isocarboxazid, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, carbutilate, ketospiradox, lankothriol, lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamitron, metazachlor, metazosulfuron, metflurazon, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napropamide-M, naphthaleneacetic acid, neburon, nicosulfuron, nipyraclofen, oxadiazon, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, pentanochlor, penthiopyrad, permethrin, phenmedipham, phenothrin, picolinafen, picoxystrobin, piperophos, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prochloraz, procymidone, profluazol, prometryn, propachlor, propanil, propazine, propisochlor, propoxur, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyrazosulfuron-ethyl, pyrazoxyfen, pyrethrins, pyributicarb, pyroxasulfone, pyroxychlor, pyroxydine, pyroxysulfone, quizalofop, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, simazine, simetryn, sulfentrazone, sulfometuron-methyl, sulfosate, sulfosulfuron, sulfotep, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thidiazuron, thiobencarb, thiodicarb, thiometon, thiram, tolclofos-methyl, topramezone, triadimefon, triadimenol, triallate, triaziflam, triazophos, tribenuron-methyl, triclopyr, tridiphane, trifluralin, trifloxysulfuron, tritosulfuron, vamidothion, vernolate, vinclozolin, ziram, zoxamide, acetochlor, alachlor, allidochlor, ametryn, amicarbazone, amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, bentazone, bifenox, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butralin, buturon, cafenstrole, carfentrazone-ethyl, chlorthal-dimethyl, chloridazon, chlorimuron-ethyl, Endosulfan, Nitralin, Nitrofen, Nitrofluorfen, Norflurazon, Noruron, OCH, Orbecarb, Ortho-dichlorobenzene, Orthosulfamuron, Oryzalin Oxadiargyl, Oxadiazon, Oxapyrasone, Oxasulfuron, Oxadi Chomephon, Oxyfluorfen, Parafluron, Paraquat, Pebulate, Peral Gonic acid, Pendimethalin, Penoxsulam, Pentachlorophenol, Pentanoclor, Pentoxazon, Perfluidone, Petoxamide, Phenisopham, Fenmedifam, Ethyl fenmedifam, Phenobenzuron, Phenylmercury acetate, Picloram, Picolina Phen, Pinoxaden, Piperophos, Potassium arsenite, Potassium azide, Potassium cyanide Pretilachlor, Primisulfuron, Prosazine, Prodiamein, Profurazo L, Profuralin, Profoxydim, Proglynadine, Prometon, Promethrin, P Lopachlor, Propanil, Propaxahop, Propazine, Profam, Propisochlor , Propoxycarbazone, Propylisulfuron, Propizamide, Protosulfalin, Pro Sulfocarb, Prosulfuron, Proxan, Prinachlor, Pidanone, Pyraclonil, Pyraflufen, Pyrazolthiol, Pyrazolineate, Pyrazosulfuron, Pyrazoxyf En, Pyribenzoxim, Pyributicarb, Pyrichlor, Pyridafol, Pyridate, P Liftalid, Pyriminobac, Pyrimisulfan, Pyrithiobac, Pyroxasulfone, Pyroxasulam, Quinclorac, Quinmerac, Quinoclamine, Quinamide, Quazalof Up, Quazalofop-P, Rotenyl, Rimsulfuron, Saffufenacil, S-Metra Chlor, Sethoxydim, Secbumeton, Cethoxydim, Shizuron, Simazine, Simeton, Simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulco trione, sulfonate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid, sulglycapin, sweep, TCA, tebutam, tebuthiuron, tefuryltrione n, tembotrione, tepraloxydim, terbacil, terbuthylazine, terbuthylazine, ter buthylazine, terbutryn, tetrafluron, tenilchlor, thiazaf luron, thiazopyr, thidiazimin, thidiazuron, thienecarbazone methyl, thifen sulfuron, thiobencarb, thiafenox, thiocarbazil, thioclorim, tolpy ralate, topramezone, traloxydim, triafamone, tri-allate, tria sulfuron, triaziflam, tribenuron, tricanba, triclopyr, tridiphane 、trietazine, trifloxysulfuron, triflumizox, trifluralin, tr iflusulfuron, trihop, trihopsim, trihydroxy triazine, trimesulo n, tripropindan, tritac, tritosulfuron, bernolate and xylachlor, but are not limited to these.

[0042] Another embodiment of the present disclosure is a method for controlling or preventing fungal attack. This method comprises applying a fungicidally effective amount of one or more compounds of Formula I to soil, plants, roots, leaves, or a location where fungi are present or a location where their occurrence is to be prevented (e.g., applying to cereal or grapevine plants). The compounds are suitable for treating a variety of plants at fungicidal levels while exhibiting low phytotoxicity. The compounds can be useful in both protectant and / or eradicator modes. ​​

[0043] The compounds have been found to have significant fungicidal effects, especially in agricultural applications. Many of the compounds are particularly effective for use on crops and horticultural plants.

[0044] The efficacy of the compounds against the aforementioned fungi establishes the general utility of the compounds as fungicides which will be understood by those skilled in the art.

[0045] The compounds have broad activity against fungal pathogens. Exemplary pathogens include Septoria tritici blotch (Zymoseptoria tritici) , wheat brown rust (Puccinia triticina) , wheat stripe rust (Puccinia striiformis) , apple scab (Venturia inaequalis) , grape powdery mildew (Uncinula necator) , barley leaf blotch (Rhynchosporium secalis) , rice blast (Magnaporthe grisea) , soybean rust (Phakopsora pachyrhizi) , wheat Septoria blotch (Parastagonospora nodorum) , wheat powdery mildew (Blumeria graminis f. sp. tritici) , barley powdery mildew (Blumeria graminis f. sp. hordei) Powdery mildew of barley (Blumeria graminis f.sp.hordei), powdery mildew of cucurbitaceous plants (Erysiphe cichoracearum), anthracnose of cucurbitaceous plants (Glomerella lagenarium), leaf spot of Chinese cabbage (Cercospora beticola), early blight of tomato (Alternaria solani), and pathogens causing spot blotch of barley (Cochliobolus sativus) can be mentioned, but are not limited thereto. The exact amount of the active material to be applied depends not only on the specific active material to be applied, but also on the specific effect desired, the species of fungus to be controlled and its growth stage, and the part of the plant or other product with which the compound is contacted. Powdery mildew of cucurbitaceous plants (Erysiphe cichoracearum) Anthracnose of cucurbitaceous plants (Glomerella lagenarium) Leaf spot of Chinese cabbage (Cercospora beticola) Early blight of tomato (Alternaria solani) And pathogens causing spot blotch of barley (Cochliobolus sativus) ), but are not limited thereto. The exact amount of the active material to be applied depends not only on the specific active material to be applied, but also on the specific effect desired, the species of fungus to be controlled and its growth stage, and the part of the plant or other product with which the compound is contacted. Therefore, all compounds and formulations containing them may not be equally effective at the same concentration or against the same species of fungus. The compounds are disease-suppressive and effective for use on plants in botanically acceptable amounts. The term "disease-suppressive and botanically acceptable amount" refers to an amount of a compound that kills or suppresses the diseases of plants for which control is desired, but is not significantly toxic to the plants. This amount is generally about 0.1 to about 1000 ppm (parts per million), preferably 1 to 500 ppm. The exact concentration of the compound required varies depending on the fungal disease to be controlled, the type of formulation used, the method of application, the species of the specific plant, the climatic conditions, etc. Suitable application rates are typically about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter). Therefore, all compounds and formulations containing them may not be equally effective at the same concentration or against the same species of fungus.

[0046] The compounds are disease-suppressive and effective for use on plants in botanically acceptable amounts. The term "disease-suppressive and botanically acceptable amount" refers to an amount of a compound that kills or suppresses the diseases of plants for which control is desired, but is not significantly toxic to the plants. This amount generally ranges from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of the compound required varies depending on the fungal disease to be controlled, the type of formulation used, the method of application, the species of the specific plant, the climatic conditions, etc. Suitable application rates are typically about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter). 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g / m 2 is in the range of.)

[0047] Any range or desired value presented in this specification can be expanded or changed without losing the sought-after effect, which is obvious to those skilled in the art who understand the teachings of this specification and is obvious to those skilled in the art who understand the teachings of this specification and is obvious to those skilled in the art who understand the teachings of this specification

[0048] The compounds of Formula I may be prepared using well-known chemical procedures. Intermediates not specifically described in this disclosure may be commercially available, prepared by routes disclosed in the chemical literature, or readily synthesized from commercially available starting materials using standard procedures and is obvious to those skilled in the art who understand the teachings of this specification and is obvious to those skilled in the art who understand the teachings of this specification and is obvious to those skilled in the art who understand the teachings of this specification

[0049] General Scheme The following scheme illustrates a method for generating picolinamide compounds of Formula (I). The following description and examples are provided for illustrative purposes and should not be construed as limiting with respect to substituents or substitution patterns and is obvious to those skilled in the art who understand the teachings of this specification and is obvious to those skilled in the art who understand the teachings of this specification

[0050] The racemic compounds of Formula 1.2-Rac, 1.3-Rac, and 1.5-Rac, 1.6-Rac [wherein R 3 is as defined beforehand] can be prepared by the method shown in Scheme 1, Step a. The racemic epoxide mixtures of Formula 1.0-Rac and 1.4-Rac and is obvious to those skilled in the art who understand the teachings of this specification in the presence of metal halides such as cuprous iodide

Chemical Formula

[0051] is as previously defined] can be resolved into their individual enantiomers using lipase-catalyzed kinetic resolution as described in Akita (Tetrahedr 3 on: Asymmetry 2009, 20, 1286-1294), which is outlined in Scheme 2, Steps a and b. The racemic mixtures of Formula 1.2-Rac, 1.3 -Rac, and 1.5-Rac, 1.6-Rac [wherein R is as previously defined] are placed in an acetylating solvent such as vinyl acetate at a temperature of about 25 °C to about 60 °C and exposed to Candida antarctica lipase B (CAL-B). -Rac, and 1.5-Rac, 1.6-Rac [wherein R 3 is as previously defined] are obtained, and the mixture is subjected to silica gel chromatography using a hexane-ethyl acetate mixture as the mobile phase. The unreacted secondary alcohol of Formula 1.2-Abs and 1.5-Abs [wherein R is as initially defined], as well as the acetylated compound of Formula 2.1-Abs and 2.3-Ab s [wherein R

Chemical Formula

[0052] 1 2 3 10 2 3 1 10 may be prepared according to the method outlined in Scheme 3, Step a. The alcohol of Formula 3.0 wherein R 2 and R 3 are as defined initially] is the compound of Formula 3.1 [wherein in the formula R 1 and R 10 are as defined initially], 3-(ethylimino (Methyleneamino)-N,N-dimethylpropane-1-amine hydrochloride (EDC) or a coupling reagent such as polymer-supported carbodiimide (PS-CDI), and N,N- dimethylpyridin-4-amine (DMAP) and the like as a catalyst, in (CH 2 Cl 2 ) or THF such as a halogenated or polar aprotic solvent in the presence of, as shown in step a , formula 3.2 [wherein R 1 , R 2 , R 3 , and R 10 are as defined initially] of the compound can be obtained.

Chemical formula

[0053] Formula 4.5 [wherein R 1 , R 2 , R 3 , R 5 , and R 10 are as defined initially there is] of the compound can be prepared according to the method outlined in Scheme 4, steps a to d can. Formula 3.2 [wherein R 1 , R 2 , R 3 , and R 10 are as defined initially there is] of the compound is in a halogenated solvent such as CH 2 Cl 2 , treated with an acid such as a 4N hydrochloric acid (HCl) solution in dioxane, as shown in step a, formula 4. 1 [wherein R , R 1 , R 2 , R 3 , and R 10 are as defined initially] of the compound can be obtained. Formula 4.2 [wherein R 1 , R 2 , R3 , and R 10 is defined first The compound of formula 3.2, wherein R 1 , R 2 , R 3 , and R 10 is as originally defined] to 2,2,2-trifluoroacetamide With acids such as acetic acid, 2 Cl 2 By treating in a halogenated solvent such as The compounds of formula 4.1 and 4.2, in which R 1 , R 2 , R 3 , and R 10 teeth , as originally defined] can be prepared by the compound of formula 4.3, 5 is defined first The compound is prepared by mixing it with a base such as diisopropylethylamine and benzotriamine. 1-Ozol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (P yBOP) or O-(7-azabenzo-triazol-1-yl)-N,N,N',N' -Peptide coupling agents such as tetramethyluronium hexafluorophosphate (HATU) In the presence of a pulling reagent, 2 Cl 2 and the like, As shown in steps b and d, a compound of formula 4.5, 1 , R 2 , R 3 , R 5 , and R 10 teeth, A compound of formula (I) can be obtained, which is as defined at the beginning. [ka]

[0054] Equation 5.1 [where R 1, R 2 , R 3 , R 5 , and R 10 are as initially defined A compound can be prepared according to the method outlined in Scheme 5, Step a or b A compound of formula 4.5 [wherein R 1 , R 2 , R 3 , R 5 , and R 10 are as initially defined can be treated in a solvent such as acetone, with or without an alkali carbonate base such as sodium carbonate (Na 2CO 2 3) or potassium carbonate 3 (K 2CO 2 3), at a temperature of about 25°C to about 50°C, with an appropriate alkyl halide and a reagent such as sodium iodide (NaI). Alternatively, or alternatively, in the presence of an amine base such as pyridine, triethylamine (NEt 3 3), DMAP, or a mixture thereof, in an aprotic solvent such as CH 2Cl 2, treating with an acyl halide or anhydride gives a compound of formula 5.1 [wherein R 3 , R , R 2 , R 2 , R , R 1 , R 2 , R 3 , R 5 , R 6 , and R 10 are as initially defined].

Chemical formula

[0055] Compounds of formulas 6.1 and 6.2 [wherein R 1 , R 2 , R 3 , R 5 , R6 and R 10 is as initially defined] The compound can be prepared according to the method outlined in Scheme 6, Steps a and b. The compound of formula 4.5 [wherein R is as initially defined] can be prepared according to the method outlined in Scheme 6, Steps a and b. The compound of formula 4.5 [wherein R , R 1 , R 2 , R 3 , R 5 , and R 10 is as initially defined] is treated with a sulfurizing reagent such as phosphorus pentasulfide and an additive such as hexamethyldisiloxane, optionally in a non-protic solvent such as acetonitrile (CH is as initially defined] is treated with a sulfurizing reagent such as phosphorus pentasulfide and an additive such as hexamethyldisiloxane, optionally in a non-protic solvent such as acetonitrile (CH CN) at a temperature of about 0 °C to 80 °C to obtain a compound of formula 6.1 [wherein R 3 is as initially defined], which is shown in Step a. Compounds such as formula 6.1 can also be prepared using other sulfurizing agents including, but not limited to, sulfur, hydrosulfuric acid (sulfhydric acid), sodium sulfide, sodium hydrosulfide, boron trisulfide, bis(diethylaluminum) sulfide, ammonium sulfide, Lawesson's reagent, O,O' 1 , etc. It will be understood by those skilled in the art. Additives include aluminum oxide (Al , R 2 , R 3 , R 5 , and R 10 is as initially defined], which is shown in Step a. Compounds such as formula 6.1 can also be prepared using other sulfurizing agents including, but not limited to, sulfur, hydrosulfuric acid can be obtained, which is shown in Step a. Compounds such as formula 6.1 can also be prepared using other sulfurizing agents including, but not limited to, sulfur, hydrosulfuric acid (sulfhydric acid), sodium sulfide, sodium hydrosulfide, boron trisulfide, bis(diethylaluminum) sulfide, ammonium sulfide, Lawesson's reagent, O,O' -ammonium diethyldithiophosphate, rhodanine, or a polymer-supported sulfurizing reagent. It will be understood by those skilled in the art. Additives include aluminum oxide (Al ); inorganic bases such as potassium carbonate and sodium bicarbonate; and organic bases such as triethylamine, diethylaniline, pyridine, and morpholine, but are not limited thereto. Optional solvents include aliphatic, alicyclic, or aromatic hydrocarbons such as hexane O 2 ); inorganic bases such as potassium carbonate and sodium bicarbonate; and organic bases such as triethylamine, diethylaniline, 3 ); inorganic bases such as potassium carbonate and sodium bicarbonate; and organic bases such as triethylamine, diethylaniline, pyridine, and morpholine, but are not limited thereto. Optional solvents include aliphatic, alicyclic, or aromatic hydrocarbons such as hexane pyridine, and morpholine, but are not limited thereto. Optional solvents include aliphatic, alicyclic, or aromatic hydrocarbons such as hexane pyridine, and morpholine, but are not limited thereto. Optional solvents include aliphatic, alicyclic, or aromatic hydrocarbons such as hexane n, cyclohexane, toluene, etc.; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chlorobenzene, etc.; ethers such as diethyl ether , 1,4-dioxane, THF, 1,2-dimethoxyethane, etc.; and other polar aprotic solvents such as pyridine and hexamethylphosphoramide (HMPA), etc. can be mentioned, but not limited thereto. In step b, the compound of formula 6.1 [wherein R 1 , R 2 , R 3 , R 5 , and R 10 are as defined initially] is treated in a polar aprotic solvent such as acetone at a temperature of about 55 °C with a suitable alkyl halide, with or without a reagent such as sodium iodide (NaI) and an alkali carbonate base such as sodium carbonate ( ) or potassium carbonate (K Na 2 CO 3 )), or in an optional aprotic solvent such as CH 2 CO 3 ) at a temperature of about 23 °C with an acyl halide or anhydride in the presence of an amine base such as pyridine, Et N, DMAP, or a mixture thereof, etc., to obtain the compound of formula 6.2 [wherein R 1 3 N, DMAP, or a mixture thereof, etc., to obtain the compound of formula 6.2 [wherein R 1 2 Cl 2 ), or in an optional aprotic solvent such as CH 1 2 , R 2 , R 3 , R 5 , R 6 , and R 10 are as defined initially]. It is possible to obtain. [Chemical formula]

[0056] Formula 7.1 [wherein, R 1 , R 2 , R 3 , R 5 , and R 10 is as defined initially a] of the compound can be prepared according to the method outlined in Scheme 7, Step a . Formula 4.5 [wherein, R 1 , R 2 , R 3 , R 5 , and R 10 is as defined initially a] of the compound is treated with an oxidizing reagent such as m-chloroperbenzoic acid (mCPBA) in a polar solvent such as CH 2 Cl 2 at a temperature of about 0 °C to 50 °C to obtain a compound of Formula 7.1 [wherein, R 1 , R 2 , R 3 , R 5 , and R 10 is as previously defined], as shown in a can be, as shown in a. Formula 7.1 [wherein, R 1 , R 2 , R 3 , R 5 , and R 10 is as defined initially] of the compound is also: hydrogen peroxide, hydrogen peroxide-urea complex complex

Chemical

[0057] Formula 8.1 [wherein, R 1 , R 2, R 3 , R 5 , and R 10 is as defined initially Certain compounds can be prepared according to the method outlined in Scheme 8, step a . Formula 4.5 [wherein R 1 , R 2 , R 3 , R 5 , and R 10 is as defined initially Certain compounds are treated with an activating carbonyl reagent such as triphosgene and a base such as pyridine , CH 2 Cl 2 etc. in a polar solvent at a temperature of about 0 °C to 50 °C to give, as shown in a so, a compound of formula 8.1 [wherein R 1 , R 2 , R 3 , R 5 , and R 10 is as defined initially can be obtained]. [Chemical formula] [Example]

[0058] Example 1A: Preparation of racemic threo-3-(2,4-dimethylphenyl)butan-2-ol Preparation. [Chemical formula] To a suspension of freshly activated magnesium turnings (1.14 g, 46.80 mmol) in anhydrous Et O (20 mL) was added 1-bromo-2,4-dimethylbenzene (8 g, 2 43.20 mmol) dropwise. The mixture was gently heated at a slight reflux (36 °C) for 5 hours (hr) . Copper(I) iodide (4. suspended in Et 2 O (50 mL) at -20 °C The resulting dark brown solution was added via syringe to a flask containing 12 g (21.61 mmol). The dark yellow suspension was stirred at -20 °C for 15 minutes (min), then cooled to -50 °C. Racemic trans-butene epoxide (1.3 g, 18.01 mmol) was added dropwise slowly, and then the reaction mixture was warmed to room temperature and stirred overnight. Next, the mixture was cooled to 0 °C, and quenched slowly by adding a saturated aqueous solution of ammonium chloride (NH 4 Cl). The mixture was filtered through a pad of celite, and the pad was rinsed thoroughly with ethyl acetate. The organic solution was washed with a saturated solution of NH Cl and brine. The solution was dried (magnesium sulfate (MgSO 4 )), filtered, and concentrated under reduced pressure. The residue was purified by automated flash column chromatography (SiO , 0 - 40% ethyl acetate / hexane gradient) 4 to afford racemic threo-3-(2,4-dimethylphenyl)butan-2-ol as a yellow oil (813 mg, 25%): H NMR (500 MHz, CDCl 2 ) δ 7 .06 (d, J = 8.5 Hz, 1H), 7.01 - 6.97 (m, 2H), 3.94 - 3 .82 (m, 1H), 2.97 (p, J = 6.9 Hz, 1H), 2.29 (d, J = 7. 1 7 Hz, 6H), 1.50 (d, J = 3.9 Hz, 1H), 1.28 (d, J = 7.0 H 3 z, 3H), 1.11 (d, J = 6.3 Hz, 3H); .06 (d, J = 8.5 Hz, 1H), 7.01 - 6.97 (m, 2H), 3.94 - 3 .82 (m, 1H), 2.97 (p, J = 6.9 Hz, 1H), 2.29 (d, J = 7. 7 Hz, 6H), 1.50 (d, J = 3.9 Hz, 1H), 1.28 (d, J = 7.0 H z, 3H), 1.11 (d, J = 6.3 Hz, 3H); 13 C NMR (126 MHz, CDCl 3 ) δ 139.99, 135.49, 135.38, 131.31, 126. 81, 126.18, 71.92, 41.42, 21.25, 20.87, 19.85, 16.06;EIMS m / z 178.

[0059] Example 1B: Preparation of racemic erythro-3-(o-tolyl)butan-2-ol [ka] Copper(I) iodide (4.15 g, 21.60 mmol) in anhydrous Et 2 O(40 mL) of 2-methylphenylmagnesium bromide (Et 2 2.0M in O, 2 After stirring for 30 minutes, orange juice was added dropwise. The orange suspension was cooled to -78 °C and racemic cis-butene epoxide (1.3 g, 18. The dry ice bath was removed and the mixture was allowed to reach ambient temperature. The mixture was cooled to 0 °C in an ice bath and diluted with NH 4 Cl saturated aqueous solution The mixture was allowed to warm to room temperature and was passed through Celite. The resulting filtrate was filtered, followed by rinsing the pad with ethyl acetate (EtOAc). H 4 The solution was then washed with saturated aqueous Cl and brine. 4 ), decrease The residue was purified by automated flash column chromatography (SiO 2 , 0 to 3 0% ethyl acetate / hexane gradient) to obtain racemic erythro-3-(o-tolyl)bromine. Tan-2-ol (2.05 g, 69%) was obtained as a yellow oil: 1 H NMR(50 0MHz,CDCl 3 )δ 7.34-7.01(m,4H),3.92(p,J=6. 3 Hz, 1H), 3.01 (p, J = 7.1 Hz, 1H), 2.36 (s, 3H), 1. 47 (s, 1H), 1.28 (d, J = 6.1 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H); 13 C NMR (126 MHz, CDCl 3 ) δ 142.14, 136 .84, 130.61, 126.49, 125.81, 72.33, 42.62, 20. 47, 19.93, 17.88; EIMS m / z 164.

[0060] Example 1C: Preparation of racemic threo-3-phenylbutan-2-ol. [Chemical formula] A suspension of copper(I) iodide (1.86 g, 9.76 mmol) in ethyl ether (18.0 mL) was added dropwise with phenyl lithium (1.9 M in butyl ether, 10.3 mL, 19.53 mmol) at 0 °C under a nitrogen atmosphere. After stirring at 0 °C for 1 hour, racemic tra ns-2,3-dimethyloxirane (0.64 g, 8.88 mmol) was added dropwise, and then the ice bath was removed and the mixture was warmed to room temperature with stirring for 2 hours. The reaction mixture was quenched with water (2 0 mL), filtered through a Celite pad, and extracted with ethyl ether (3 × 20 mL ). The organic substances were passed through a phase separator and concentrated under reduced pressure. The crude residue was purified by automatic flash silica column chromatography (SiO 2 , 0 - 25% acetone / hexane gradient) to obtain racemic threo-3-phenylbutan-2-ol (1.33 g, 8.85 mmo l, 99%) as an orange oil: 1 H NMR (400 MHz, CDCl 3 )δ 7.38 - 7.12 (m, 5H), 3.91 - 3.84 (m, 1H), 2.80 - 2.68 (m, 1H), 1.43 (s, 1H), 1.33 (d, J = 7.1 Hz, 3H) , 1.09 (d, J = 6.3 Hz, 3H). The spectral data was consistent with that reported in the literature: Tetrahe dron 1981, 37, 709 - 713

[0061] Example 2: Preparation of (2S,3S)-3-(2,4-dimethylphenyl)butan-2-ol and (2R,3R)-3-(2,4-dimethylphenyl)butan-2-ol Step 1: Preparation of (2S,3S)-3-(2,4-dimethylphenyl)butan-2-ol and ( (2R,3R)-3-(2,4-dimethylphenyl)butan-2-yl acetate

Chemical Structure

[0062] Step 2: Preparation of (2R,3R)-3-(2,4-dimethylphenyl)butan-2-ol .

Chemical formula

[0063] Example 3: Preparation of (2S,3S)-3-phenylbutan-2-yl (tert-butoxycarbonyl)-L-alaninate

Chemical Structure

[0064] Example 4: Preparation of (2S,3S)-3-phenylbutan-2-yl (3-hydroxy-4-meth oxypicolinoate)-L-alaninate. Step 1: Preparation of (2S,3S)-3-phenylbutan-2-yl-L-alaninate hydrochloride. To the crude (2S,3S)-3-phenylbutan-2-yl (tert-butoxycarbonyl)-L-alaninate (0.42 g, 1.31 mmol) as such, a solution of HCl (4 M, 3.3 mL, 13.07 mmol) dissolved in dioxane was added dropwise under nitrogen. After stirring for 16

Chemical Structure

[0065] Step 2: Preparation of (2S,3S)-3-phenylbutan-2-yl (3-hydroxy-4-methoxypicolinoate)-L-alaninate. ​ [Chemical formula] (2S,3S)-3-Phenylbutan-2-yl-L-alaninate hydrochloride was dissolved in methylene chloride (6.5 mL), 3-hydroxy-4-methoxypicolinic acid (0.2 4 g, 1.44 mmol), and a solution of (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.75 g, 1.44 mmol) was added dropwise with N,N-diisopropylethylamine (0.75 mL, 4.31 mmol) under nitrogen. After stirring for 16 hours, the reaction mixture was concentrated in vacuo. The crude residue was purified by automated flash column chromatography (SiO (0 - 45% acetone / hexane gradient) to give 2 (2S,3S)-3-Phenylbutan-2-yl (3-hydroxy-4-methoxypicolinoyl)-L-alaninate (0.46 g, 1.173 mmol, 90% yield) as a colorless oil: (2S,3S)-3-Phenylbutan-2-yl (3-hydroxy-4-methoxypicolinoyl)-L-alaninate (0.46 g, 1.173 mmol, 90% yield) was obtained as a colorless oil: 1 1H NMR (500 MHz, CDCl 3 ) δ 12.16 ( s, 1H), 8.50 (d, J = 8.0 Hz, 1H), 8.01 (d, J = 5.2 Hz, 1H), 7.32 - 7.27 (m, 2H), 7.24 - 7.16 (m, 3H), 6.88 (d, J = 5.2 Hz, 1H), 5.11 (dq, J = 7.7, 6.3 Hz, 1H), 4 .77 - 4.67 (m, 1H), 3.95 (s, 3H), 2.97 - 2.87 (m, 1H ), 1.54 (d, J = 7.2 Hz, 3H), 1.31 (d, J = 7.0 Hz, 3H), 1.13 (d, J = 6.3 Hz, 3H); IR (thin film) 2978, 2937, 1733, 1647, 1527, 1451, 1262, 1147, 701 cm-1 ; HRMS-ES I (m / z) [M+H]+ C 20 H 25 N 2 O 5 Calculated value, 373.1758; Measured value, 373.1752.

[0066] Example 5A: Preparation of (2S,3S)-3-phenylbutan-2-yl (3-acetoxy-4-meth oxy-picolinoate)-L-alaninate.

Chemical Structure

[0067] Example 5B: Preparation of (2S,3R)-3-(o-tolyl)butan-2-yl (3-(acetoxymethoxy )-4-methoxypicolinoate).

Chemical Structure

[0068] Example 5C: Preparation of 4 - methoxy - 2 - (((S) - 1 - oxo - 1 - (((2S,3S) - 3 -(2 - (trifluoromethyl)phenyl)butan - 2 - yl)oxy)propan - 2 - yl)carbamoyl)pyridin - 3 - yl isobutyrate.

Chemical Structure

[0069] Example 6: Preparation of (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl (3- acetoxy-4-methoxypyridine-2-carbonothioyl)-L-alaninate . Step 1: Preparation of (2S,3S)-3-(2-(trifluoromethyl)phenyl)butan-2-yl (3-hydroxy-4-methoxypyridine-2-carbonothioyl)-L-alaninate .

Chemical Structure

[0070] Step 2: Preparation of (2S,3S)-3-(2-(trifluoromethyl)phenyl)butan-2-yl (3-acetoxy-4-methoxypyridine-2-carbonothioyl)-L-alaninate.

Chemical Structure

[0071] Example 7: Preparation of 3-hydroxy-4-methoxy-2-(((S)-1-oxo-1-(((2 (S,3S)-3-phenylbutan-2-yl)oxy)propan-2-yl)carbamoyl pyridine 1-oxide.

Chem.

[0072] ​​Example 8: Preparation of (2S,3S)-3-phenylbutan-2-yl (S)-2-(8-methoxy -2,4-dioxo-2H-pyrido[2,3-e][1,3]oxazin-3(4H)- yl)propanoate.

Chemical formula

[0073] Example A: Evaluation of fungicidal activity: Wheat leaf blotch (Septoria tritici (Zymos eptoria tritici); Bayer code SEPTTR): The material of the industrial brand was dissolved in acetone and then mixed with 9 volumes of water containing 110 ppm of Triton X-1 00. The fungicide solution was applied using an automated booth sprayer until it ran off the wheat seedlings. All the sprayed plants were air-dried before further handling. Unless otherwise specified, all fungicides were evaluated for their activity against all target diseases using the method described above. The activity against wheat leaf blotch and brown rust was also evaluated using track spray application, in which case the fungicide was formulated as an EC formulation containing 0.1% Trycol 594 1 in the spray liquor.

[0074] Wheat plants (cultivar Yuma) were grown from seeds in 50% mineral soil / 50% soilless Metro Mix in the greenhouse until the first leaf was fully emerged, with 7 - 10 seedlings per pot. These plants were inoculated with Septoria either before or after the fungicide treatment. Inoculated with an aqueous spore suspension of Zymoseptoria tritici After inoculation, the plants were kept at 100% relative humidity (in a dark fog chamber at 20 °C for 1 day, followed by a lighted fog chamber at 20 °C for 2 - 3 days) to germinate the spores and infect the leaves. Next the plants were transferred to a greenhouse set at 20 °C to allow the disease to develop. When the symptoms of the disease were fully expressed on the first leaf of the untreated plants, the infection level was evaluated on a scale of 0 - 100 percent disease severity The percent disease control was calculated using the ratio of the disease severity of the treated plants to that of the untreated plants

[0075] Example B: Evaluation of fungicidal activity: Wheat leaf rust (Puccinia triticina (Pucc inia triticina); synonym: Puccinia recondita f.sp. tritici; Bayer code PUC CRT): Wheat plants (cultivar Yuma) were grown from seeds in 50% mineral soil / 50% soilless Metr o Mix in the greenhouse until the first leaf was fully emerged, with 7 - 10 seedlings per pot These plants were inoculated with an aqueous spore suspension of Puccinia triticina either before or after treatment with the fungicide After inoculation, the plants were kept in a dark fog chamber at 22 °C at 100% relative humidity overnight to germinate the spores and infect the leaves. Then the plants were transferred to a greenhouse set at 24 °C to allow the disease to develop The fungicidal formulations, applications, and disease evaluations were carried out according to the procedure described in Example A

[0076] Example C: Evaluation of fungicidal activity: Asian soybean rust (Phakopsora pachyrhizi (Phak ​​​Phakopsora pachyrhizi); Bayer code PHAKPA): The material of the industrial brand was dissolved in acetone and then mixed with 9 volumes of water containing 0.011% Tween 20 The fungicide solution was applied using an automatic sprayer until it ran off the soybean seeds All the sprayed plants were air-dried before further handling.

[0077] Soybean plants (cultivar Williams 82) were grown in soilless Metro Mix at one plant per pot Seedlings at 2 weeks old were used for the test. The plants were inoculated either 3 days or 1 day after the fungicide treatment The plants were incubated in a dark fog chamber at 22 °C and 100% relative humidity for 24 hours and then transferred to a growth chamber at 23 °C for the disease to develop The severity of the disease was evaluated on the sprayed leaves.

[0078] Example D: Evaluation of fungicidal activity: Tomato early blight (Alternaria solani ); Bayer code ALTESO): Tomato plants (cultivar Outdoor Girl) were propagated in soilless Metro Mix in pots with one plant each and used at 12 - 14 days old The test plants were inoculated with an aqueous spore suspension of Alternaria solani 24 hours after the fungicide treatment After inoculation, the plants were kept at 100% relative humidity (in a dark fog chamber at 20 °C for 1 day and then in a lighted fog chamber for 2 - 3 days) to germinate the spores and infect the leaves Then the plants were transferred to a growth chamber at 22 °C for the disease to develop The evaluation of the fungicidal formulation, application, and disease in the sprayed leaves followed the procedure described in Example A

[0079] ​​​​ Example E: Evaluation of fungicidal activity: Leaf spot of sugar beet (Cercospora beticola; Bayer code CERCBE): Sugar beet plants (cultivar HH88) were grown in soil-less Metro Mix and regularly trimmed to maintain a uniform plant size prior to testing. The plants were inoculated with a spore suspension 24 hours after fungicide treatment. The inoculated plants were kept in a mist chamber at 22 °C for 48 hours and then incubated in a clear plastic hood with bottom ventilation at 24 °C in a greenhouse until the symptoms of the disease were fully developed. The evaluation of the fungicidal formulation, application, and disease on the sprayed leaves followed the procedure described in Example A. Sugar beet plants (cultivar HH88) were grown in soil-less Metro Mix and regularly trimmed to maintain a uniform plant size prior to testing. The plants were inoculated with a spore suspension 24 hours after fungicide treatment. The inoculated plants were kept in a mist chamber at 22 °C for 48 hours and then incubated in a clear plastic hood with bottom ventilation at 24 °C in a greenhouse until the symptoms of the disease were fully developed. The evaluation of the fungicidal formulation, application, and disease on the sprayed leaves followed the procedure described in Example A. The evaluation of the fungicidal formulation, application, and disease on the sprayed leaves followed the procedure described in Example A.

[0080] Example F: Evaluation of fungicidal activity: Anthracnose of cucumber (Glomerella lagenarium; anamorph: Colletotrichum lagenarium; Bayer code COLLLA): Cucumber seedlings (cultivar Bush Pickle) were propagated in soil-less Metro Mix in pots, each with one plant, and used in the test at 12 - 14 days old. The test plants were inoculated with an aqueous spore suspension of Colletotrichum lagenarium 24 hours after fungicide treatment. After inoculation, the plants were kept in a mist chamber at 22 °C with 100% relative humidity for 48 hours to germinate the spores and infect the leaves. Cucumber seedlings (cultivar Bush Pickle) were propagated in soil-less Metro Mix in pots, each with one plant, and used in the test at 12 - 14 days old. The test plants were inoculated with an aqueous spore suspension of Colletotrichum lagenarium 24 hours after fungicide treatment. After inoculation, the plants were kept in a mist chamber at 22 °C with 100% relative humidity for 48 hours to germinate the spores and infect the leaves. After inoculation, the plants were kept in a mist chamber at 22 °C with 100% relative humidity for 48 hours to germinate the spores and infect the leaves. After inoculation, the plants were kept in a mist chamber at 22 °C with 100% relative humidity for 48 hours to germinate the spores and infect the leaves. The plants were then transferred to a growth chamber set at 22 °C for the disease to develop. The evaluation of the fungicidal formulation, application, and disease on the sprayed leaves followed the procedure described in Example A.

[0081] Example G: Evaluation of fungicidal activity: Wheat leaf blotch (Parastagonospora nodorum; Bayer code LEPTNO): rastagonospora nodorum); Bayer code LEPTNO): Wheat plants (cultivar Yuma) were grown from seeds in 50% mineral soil / 50% soilless Metro Mix at 7 - 10 seedlings per pot until the first leaf was fully emerged. These plants were inoculated with an aqueous spore suspension of Parastagonospora nodorum 24 hours after the fungicide treatment. After inoculation, the plants were kept at 100% relative humidity (1 day in a dark fog chamber at 20°C, followed by 2 days in a lighted fog chamber) to germinate the spores and infect the leaves. Then the plants were transferred to a greenhouse set at 20°C to allow the disease to develop. The fungicidal formulations, application, and disease evaluation were carried out according to the procedure described in Example A.

[0082] Example H: Evaluation of fungicidal activity: Cucumber downy mildew (Pseudoperonospora cubensis; Bayer code PSP (Pseudoperonospora cubensis); Bayer code PSP ECU): Cucumber seedlings (cultivar Bush Pickle) were grown in soilless Metro Mix at 1 plant per pot and used in the test at 12 - 14 days old. The plants were inoculated with a spore suspension 24 hours after the fungicide treatment. The test plants were inoculated with an aqueous spore suspension of Pseudoperonospora cubensis 24 hours after the fungicide treatment. After inoculation, the plants were kept in a fog chamber at 22°C and 100% relative humidity for 24 hours to germinate the spores and infect the leaves. Next, the plants were kept in a fog chamber at 22°C and 100% relative humidity for 24 hours to germinate the spores and infect the leaves. Next, the plants It was transferred to a greenhouse set at 20 °C until the disease fully manifested. Fungicidal preparations, application, and The evaluation of the disease in the sprayed leaves followed the procedure described in Example A.

[0083] Example I: Evaluation of fungicidal activity: Blast of rice (Magnaporthe grisea (Magnap orthe grisea); Anamorph: Pyricularia oryzae); Bayer code PYRIOR): Rice seedlings (cultivar Japonica) were propagated in pots with 8 - 14 plants each in soil - less Metro Mix and used in the test when they were 12 - 14 days old. The test plants were inoculated with an aqueous spore suspension of Pyricularia oryzae 24 hours after the fungicide treatment. After inoculation, the plants were kept in a fog chamber at 100% relative humidity and 2 2 °C for 48 hours to germinate the spores and infect the leaves. Then the plants were transferred to a greenhouse set at 24 °C so that the disease would develop. The evaluation of the fungicidal preparations, application, and the disease in the sprayed leaves followed the procedure described in Example A. 20 °C for 48 hours to germinate the spores and infect the leaves. Next, the plants were transferred to a greenhouse set at 24 °C so that the disease would develop. The evaluation of the fungicidal preparations, application, and the disease in the sprayed leaves followed the procedure described in Example A.

[0084] Example J: Evaluation of fungicidal activity: Net blotch of barley (Rhynchosporium secalis (Rhyn chosporium secalis); Bayer code RHYNSE): Barley seedlings (cultivar Harrington) were propagated in pots with 8 - 12 plants each in soil - less Metro Mix and used in the test when the first leaf had fully emerged. The test plants were inoculated with an aqueous spore suspension of Rhynchosporium secalis 24 hours after the fungicide treatment. After inoculation, the plants were inoculated with an aqueous spore suspension of Rhynchosporium secalis 24 hours after the fungicide treatment. After inoculation, the plants chosporium secalis) 24 hours after the fungicide treatment. After inoculation, the plants The object was kept in a fog chamber at 20 °C with 100% relative humidity for 48 hours. Next, the plants were transferred to a greenhouse set at 20 °C so that the disease would develop. The evaluation of the fungicidal preparation, application, and disease in the sprayed leaves was carried out according to the procedure described in Example A. The evaluation of the fungicidal preparation, application, and disease in the sprayed leaves was carried out according to the procedure described in Example A. The evaluation of the fungicidal preparation, application, and disease in the sprayed leaves was carried out according to the procedure described in Example A.

[0085] Example K: Evaluation of fungicidal activity: Powdery mildew of grapevine (Uncinula necator: Bayer code UNCINE): Example K: Evaluation of fungicidal activity: Powdery mildew of grapevine (Uncinula necator: Bayer code UNCINE): Grapevine seedlings (cultivar Carignane) were grown in soil-free Metro Mix at one plant per pot and used in the test at approximately one month of age. The plants were inoculated 24 hours after the fungicide treatment by shaking spores from the infected leaves onto the test plants. Grapevine seedlings (cultivar Carignane) were grown in soil-free Metro Mix at one plant per pot and used in the test at approximately one month of age. The plants were inoculated 24 hours after the fungicide treatment by shaking spores from the infected leaves onto the test plants. Grapevine seedlings (cultivar Carignane) were grown in soil-free Metro Mix at one plant per pot and used in the test at approximately one month of age. The plants were inoculated 24 hours after the fungicide treatment by shaking spores from the infected leaves onto the test plants. The plants were maintained in a greenhouse set at 20 °C until the disease had fully developed. The evaluation of the fungicidal preparation, application, and disease in the sprayed leaves was carried out according to the procedure described in Example A. The evaluation of the fungicidal preparation, application, and disease in the sprayed leaves was carried out according to the procedure described in Example A.

[0086] [Table 1]

[0087] [Table 2]

[0088] [Table 3]

[0089] [Table 4]

[0090] [Table 5]

[0091]

Table 6

[0092]

Table 7

[0093]

Table 8

[0094]

Table 9

[0095]

Table 10

[0096]

Table 11

[0097]

Table 12

[0098]

Table 13

[0099]

Table 14

[0100]

Table 15

[0101]

Table 16

[0102]

Table 17

[0103]

Table 18

[0104]

Table 19

[0105]

Table 20

[0106]

Table 21

[0107]

Table 22

[0108]

Table 23

[0109]

Table 24

[0110]

Table 25

[0111]

Table 26

[0112]

Table 27

[0113]

Table 28

[0114]

Table 29

[0115]

Table 30

[0116]

Table 31

[0117]

Table 32

[0118]

Table 33

[0119]

Table 34

[0120]

Table 35

[0121]

Table 36

[0122]

Table 37

[0123]

Table 38

[0124]

Table 39

[0125]

Table 40

[0126]

Table 41

[0127]

Table 42

[0128]

Table 43

[0129]

Table 44

[0130]

Table 45

[0131]

Table 46

[0132]

Table 47

[0133]

Table 48

[0134]

Table 49

[0135]

Table 50

[0136]

Table 51

[0137]

Table 52

[0138]

Table 53

[0139]

Table 54

[0140]

Table 55

[0141]

Table 56

[0142]

Table 57

[0143]

Table 58

[0144]

Table 59

[0145]

Table 60

[0146]

Table 61

[0147]

Table 62

[0148]

Table 63

[0149]

Table 64

[0150]

Table 65

[0151]

Table 66

[0152]

Table 67

[0153]

Table 68

[0154]

Table 69

[0155]

Table 70

[0156]

Table 71

[0157]

Table 72

[0158]

Table 73

[0159]

Table 74

[0160]

Table 75

[0161]

Table 76

[0162]

Table 77

[0163]

Table 78

[0164]

Table 79

[0165]

Table 80

[0166]

Table 81

[0167]

Table 82

[0168]

Table 83

[0169]

Table 84

[0170]

Table 85

[0171]

Table 86

[0172]

Table 87

[0173]

Table 88

[0174]

Table 89

[0175]

Table 90

[0176]

Table 91

[0177]

Table 92

[0178]

Table 93

[0179]

Table 94

[0180]

Table 95

[0181]

Table 96

[0182]

Table 97

[0183]

Table 98

[0184]

Table 99

[0185]

Table 100

[0186]

Table 101

[0187]

Table 102

[0188]

Table 103

[0189]

Table 104

[0190]

Table 105

[0191]

Table 106

[0192]

Table 107

[0193]

Table 108

[0194]

Table 109

[0195]

Table 110

[0196]

Table 111

[0197]

Table 112

[0198]

Table 113

[0199]

Table 114

[0200]

Table 115

[0201]

Table 116

[0202]

Table 117

[0203]

Table 118

[0204]

Table 119

[0205]

Table 120

[0206]

Table 121

[0207]

Table 122

[0208]

Table 123

[0209]

Table 124

[0210]

Table 125

[0211]

Table 126

[0212]

Table 127

[0213]

Table 128

[0214]

Table 129

[0215]

Table 130

[0216]

Table 131

[0217]

Table 132

[0218]

Table 133

[0219]

Table 134

[0220]

Table 135

[0221]

Table 136

[0222]

Table 137

[0223]

Table 138

[0224]

Table 139

[0225]

Table 140

[0226]

Table 141

[0227]

Table 142

[0228]

Table 143

[0229]

Table 144

[0230]

Table 145

[0231]

Table 146

[0232]

Table 147

[0233]

Table 148

[0234]

Table 149

[0235]

Table 150

[0236]

Table 151

[0237]

Table 152

[0238]

Table 153

[0239]

Table 154

[0240]

Table 155

[0241]

Table 156

[0242]

Table 157

[0243]

Table 158

[0244]

Table 159

[0245]

Table 160

[0246]

Table 161

[0247]

Table 162

Claims

1. Formula (I) 【Chemistry 1】 [In the formula, Q is, 【Chemistry 2】 and X is hydrogen or C(O)R ４ and Y is hydrogen or C(O)R ４ and Z is N or N ＋ →O － and W is O or S; R １ is hydrogen or alkyl, and zero, one or more R ７ is substituted with; R ２ is methyl; R ３ are alkyl, aryl, or heteroaryl, each of which may be zero, one, or more R ７ and optionally substituted with R ４ is alkoxy or benzyloxy, each of which is zero, one, or more R ７ Any is optionally substituted; R ５ is hydrogen, alkoxy, or halo, each of which is zero, one, or more R ７ Select at random is selectively substituted; R ６ is hydrogen, -C(O)R ８ , or -CH ２ O.C.(O)R ８ and R ７ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy cycloalkyl, cycloalkyl, cyclohexyl ... ９ Optional has been replaced by; R ８ is alkyl, alkoxy, or aryl, each of which may have zero, one, or more R ７ and optionally substituted with R ９ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heptane. is rocyclyl; R １０ is hydrogen or alkyl, each of which may contain zero, one, or more R ７ has been replaced with ] compound.

2. Q 【Chemistry 3】 and X and Y are hydrogen.

3. R １ and R １０ is independently selected from hydrogen or alkyl. thing.

4. R ３ is aryl and zero, one or more R ７ Optionally substituted with The compound according to claim 2.

5. R １ and R １０ is independently selected from hydrogen or alkyl; R ３ is aryl, and 0 , one or more R ７ 3. The compound of claim 2, optionally substituted with

6. Q 【Chemistry 4】 and X is C(O)R ４ and Y is hydrogen.

7. R １ and R １０ is independently selected from hydrogen or alkyl. thing.

8. R ３ is aryl and zero, one or more R ７ Optionally substituted with The compound according to claim 6.

9. R １ and R １０ is independently selected from hydrogen or alkyl; R ３ is aryl, and 0 , one or more R ７ 7. The compound of claim 6, optionally substituted with

10. Q 【Chemistry 5】 2. The compound of claim 1, wherein X is hydrogen.

11. The compound of claim 10 wherein Z is N.

12. The compound of claim 11 , wherein W is O.

13. R ５ The compound of claim 12, wherein is alkoxy.

14. R ６ The compound of claim 13, wherein is hydrogen.

15. R １ and R １０ is independently selected from hydrogen or alkyl. Compound.

16. R ３ is aryl and zero, one or more R ７ Optionally substituted with The compound according to claim 14.

17. R １ and R １０ is independently selected from hydrogen or alkyl; R ３ is aryl, and 0 , one or more R ７ 15. The compound of claim 14, optionally substituted with

18. R ６ But -C(O)R ８ or -CH ２ O.C.(O)R ８ 14. The compound of claim 13, selected from:

19. R １ and R １０ is independently selected from hydrogen or alkyl. Compound.

20. R ３ is aryl and zero, one or more R ７ Optionally substituted with 19. The compound according to claim 18.

21. R １ and R １０ is independently selected from hydrogen or alkyl; R ３ is aryl, and 0 , one or more R ７ 20. The compound of claim 18, optionally substituted with:

22. A fungicidal composition comprising any one of the compounds according to claims 1 to 21.

23. The composition may comprise one or more of a fungicide, an insecticide, a nematicide, an acaricide, an arthropodicide, 23. The composition of claim 22, further comprising a fungicide, and combinations thereof.

24. At least one of the compounds according to claims 1 to 21 and a fungicide, insecticide or nematicide Other pesticides, including miticides, arthropodicides, fungicides, and combinations thereof.

5. A composition for controlling fungal pathogens comprising a mixture of the compound and an agent.

25. The fungal pathogen is Zymoseptoria tritici, which causes wheat leaf spot. wheat brown rust (Puccinia tritici) nia triticina), wheat leaf rust (Puccinia striiformis (P uccinia striiformis), apple scab (Venturia inaeku) Alice (Venturia inaequalis), corn smut (Usti Ustilago maydis), Grape powdery mildew (Uncinula Uncinula necator), barley scald (Rhynchosporium - Rhynchosporium secalis), rice blast disease (P. oryzae) Pyricularia oryzae), soybean rust ( Phakopsora pachyrhizi, wheat follicle Shoot blight (Parastagonaspora nodorum) orum), powdery mildew of wheat (Blumeria graminis triticiformes (Blumeria ria graminis f. sp. tritici), powdery mildew of barley (Bryophyllum gracilis f. sp. tritici) Blumeria graminis f.sp. hordei), powdery mildew of cucurbits (Erysiphe scoracearum phe cichoracearum), anthracnose of cucurbits (Colletotrichum lagens) Colletotrichum lagenarium), and leaves of the Chinese cabbage Leaf spot (Cercospora beticola), tomato Summer blight of cucumber (Alternaria solani), Downy mildew of Chinese chili pepper (Pseudoperonospora cubensis) a cubensis), and net blotch of barley (Pyrenophora teres).

25. The composition of claim 24, wherein the glycerol is one of the following: phora teres.

26. The fungal pathogen is Zymoseptoria tritici, which causes wheat leaf spot. wheat brown rust (Puccinia tritici) nia triticina), barley scald (Rhynchosporium secharis (Rh syncosporium secalis), rice blast disease (Pyricularia oryzae) Pyricularia oryzae), soybean rust (Phakopsora Phakopsora pachyrhizi), wheat gall blight (Pallas Parastagonospora nodorum, U Anthracnose of Limacaceae (Colletotrichum lagenarium) agenarium), leaf spot disease of spinach (Cercospora beticola (Cercospora pora beticola), grape powdery mildew (Uncinula necator (Unci nula necator), cucumber downy mildew (Pseudoperonospora cubensis Pseudoperonospora cubensis, and tomato late blight (Alternaria solani) The composition of claim 24.

27. 1. A method for controlling and preventing fungal attack on plants, comprising: A fungicidally effective amount of at least one of the compounds according to any one of claims 1 to 21. a plant; an area adjacent to the plant; and soil adapted to support the growth of the plant. to at least one of the roots of the plant and the leaves of the plant.

28. 1. A method for controlling and preventing fungal attack on plants, comprising: A fungicidally effective amount of at least one of the compositions according to any one of claims 22 to 23. a soil layer adapted to support the growth of the plant; applying to at least one of the soil, the roots of the plant, and the leaves of the plant. 。

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