Fungicidal aryl amidines

Abstract

To provide a compound that serves as an effective fungicide against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.SOLUTION: An arylamidine of formula I is used as a fungicide. (R1 is H, C1 to C8 alkyl, C5 to C7 heteroaryl, and the like; R2 to R5 are independently H, C1 to C8 alkyl, and the like; R6 is H, C1 to C8 alkyl, and the like; R7 and R8 are independently H, C1 to C8 alkyl, C1 to C8 substituted alkyl, and the like, or may be joined together through covalent bonding to form a saturated or unsaturated C3 to C8 heterocycloalkyl or C3 to C8 substituted heterocycloalkyl group).SELECTED DRAWING: None

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This disclosure is incorporated herein by reference in its entirety. This application claims the benefit of US Pat. No. 6,393,363, which is expressly incorporated herein by reference. To be incorporated. [Background technology]

[0002] Fungicides protect and inhibit plants against damage caused by agronomically relevant fungi. and / or compounds of natural or synthetic origin that act to treat. There is no single fungicide that is useful. Therefore, there are many options that may have good performance and are easy to use. Research is underway to produce easier and less costly fungicides. Summary of the Invention [Means for solving the problem]

[0003] The present disclosure relates to aryl amidines and their use as fungicides. may provide protection against Ascomycota, Basidiomycota, Imperfectimycota and Oomycota.

[0004] One embodiment of the present disclosure is a compound of formula I: [ka] (In the formula, R 1 is hydrogen, C1-C8 alkyl, C1-C8 substituted alkyl, C2-C8 alkenyl, C2-C8 substituted alkenyl, C2-C8 alkynyl, C2-C8 substituted alkynyl, C3- C8 cycloalkyl, C3-C8 substituted cycloalkyl, C3-C8 heterocycloalkyl , C3-C8 substituted heterocycloalkyl, C5-C7 heteroaryl, C5-C7 substituted aryl Selected from the group consisting of aryl, phenyl, substituted phenyl, benzyl and substituted benzyl Is; Each R 2 , R 3 , R 4 and R 5 are independently hydrogen, halogen, cyano, nitro, C1-C 8 alkyl, C1-C8 substituted alkyl, C2-C8 alkenyl, C2-C8 substituted alkenyl C2-C8 alkynyl, C2-C8 substituted alkynyl, C1-C8 alkoxy and C1 ~C8 substituted alkoxy; R 6 is hydrogen, C1-C8 alkyl, C1-C8 substituted alkyl, C2-C8 alkenyl, C2-C8 substituted alkenyl, C2-C8 alkynyl, C1-C8 substituted alkynyl, C1- C8 alkoxy, C1-C8 substituted alkoxy, thiol, alkylthio and substituted alkyl or R 6 and R 7 are covalently bonded together and form a saturated or unsaturated C3-C8 heterocycloalkane. may form a C3-C8 substituted heterocycloalkyl group; Each R 7 and R 8 are independently hydrogen, C1-C8 alkyl, C1-C8 substituted alkyl, C 2~C8 alkenyl, C2~C8 substituted alkenyl, C2~C8 alkynyl, C2~C8 substituted substituted alkynyl, C3-C8 cycloalkyl, C3-C8 substituted cycloalkyl, phenyl, is selected from the group consisting of substituted phenyl, benzyl, and substituted benzyl; or R 7 and R 8 are covalently bonded together and form a saturated or unsaturated C3-C8 heterocycloalkane. may form a C3-C8 substituted heterocycloalkyl group; Any heterocyclic ring may contain up to three heteroatoms selected from the group consisting of O, N and S. (may contain or a tautomer or salt thereof.

[0005] Another embodiment of the present disclosure is a method for the preparation of a phytochemically acceptable carrier material comprising the above-mentioned compound. It may include a fungicidal composition to control or prevent fungal attack.

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

[0007] The following terms may include generic "R" groups within their definitions, e.g., the term It will be understood by those of ordinary skill in the art that alkoxy refers to an -OR substituent. Within the definition of the term, these "R" groups are included for illustrative purposes and are intended to be understood to mean The substitutions in the formula I are not intended to be construed as limiting all substitutions or being limited by the substitutions in the formula I. It is also understood that it should not be.

[0008] The term "alkyl" refers to a branched, unbranched, or saturated acyclic alkyl group consisting of carbon and hydrogen atoms. Refers to the substituents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary Including, but not limited to, butyl, pentyl, hexyl and the like.

[0009] The term "alkenyl" refers to an acyclic, unsaturated (at least one carbon atom) group consisting of carbon and hydrogen. -carbon double bond), branched or unbranched substituents, including ethenyl, propenyl, butenyl, These include, but are not limited to, isopropenyl, isobutenyl, and the like.

[0010] The term "alkynyl" refers to an acyclic, unsaturated (at least one carbon atom) group consisting of carbon and hydrogen. -carbon triple bond), branched or unbranched substituents, such as ethynyl, propargyl, butyric acid, It refers to aryl and pentynyl.

[0011] The term "cycloalkenyl" refers to a monocyclic or polycyclic unsaturated (at least Substituents of at least one carbon-carbon double bond, e.g., cyclobutenyl, cyclopentenyl , cyclohexenyl, norbornenyl, bicyclo[2.2.2]octenyl, tetrahydrofuran It refers to lonaphthyl, hexahydronaphthyl and octahydronaphthyl.

[0012] The term "cycloalkyl" refers to a monocyclic or polycyclic saturated substituent consisting of carbon and hydrogen, e.g. For example, cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2 .2] Refers to octyl and decahydronaphthyl.

[0013] The term "cycloalkoxy" refers to a cycloalkyl consisting of a carbon-oxygen single bond, e.g., cycloalkoxy. cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[2.2.2]octyloxy.

[0014] The terms "aryl" and "Ar" refer to any aromatic monocyclic ring containing zero heteroatoms. Or bicyclic, for example phenyl and naphthyl.

[0015] The term "heteroaryl" refers to any aromatic monocyclic or aryl ring containing one or more heteroatoms. refers to bicyclic rings, e.g., pyridinyl, piperazinyl and thiophenyl.

[0016] The term "heterocycloalkyl" refers to a group consisting of carbon and hydrogen atoms and one or more heteroatoms. "R" refers to any non-aromatic monocyclic or bicyclic ring containing:

[0017] The term "alkoxy" refers to an --OR substituent.

[0018] The term "cyano" refers to a -C≡N substituent.

[0019] The term "amino" refers to an --N(R)2 substituent.

[0020] The term "halogen" or "halo" refers to one or more of the following radicals defined as F, Cl, Br, and I. Refers to a halogen atom.

[0021] The term "nitro" refers to a -NO2 substituent.

[0022] The term "thiol" refers to a --SH substituent.

[0023] The term "alkylthio" refers to an --SR substituent.

[0024] The term "benzyl" refers to a -CH2-phenyl substituent.

[0025] Throughout this disclosure, references to compounds of formula I include all stereoisomers thereof, e.g., diazonium salts, It is understood that the present invention is intended to include stereomers, enantiomers and mixtures thereof. In this form, formula (I) is to be read as including salts and hydrates thereof. Exemplary salts include The hydrochloride, hydrobromide, hydroiodide, trifluoroacetate and trifluoroacetate are These include, but are not limited to, trifluoromethanesulfonate.

[0026] The laws of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity It will also be understood by one of ordinary skill in the art that further substitutions may be tolerated unless otherwise indicated.

[0027] Another embodiment of the present disclosure is to administer a compound of formula I or a composition comprising the compound to soil, plants, or plants. protection of plants against attack by phytopathogenic organisms, including application to the leaves and / or roots of the plants. Use of compounds of formula I for the protection or treatment of plants infested by phytopathogenic organisms be.

[0028] In addition, another embodiment of the present disclosure is a method for preparing a pharmaceutical composition comprising a compound of formula I and a phytologically acceptable carrier material. and / or to protect plants against attack by phytopathogenic organisms, including The composition is useful for treating plants infested with DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0029] The compounds of the present disclosure can be administered in any of a variety of known techniques, either as a compound or as a formulation containing the compound. For example, the compounds can be applied to a wide variety of true plants without compromising the commercial value of the plants. The materials may be applied to the roots or foliage of plants for fungal control. For example, they can be applied in the form of a liquid formulation, a dust formulation, a wettable powder, a flowable formulation or an emulsifiable concentrate.

[0030] Preferably, the compounds of the present disclosure are prepared by combining one or more compounds of formula I in a phytologically acceptable carrier. Concentrated formulations are applied in the form of a formulation containing water or other liquid for application. The formulation may be in the form of a powder or granules, which may then be further processed. The formulations may be prepared according to procedures conventional in the agrochemical art. It can be manufactured.

[0031] The present disclosure may be formulated so that one or more compounds are delivered and used as a fungicide. All vehicles that can be used are contemplated. Typically, the formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions are usually prepared by mixing water-soluble solids known as wettable powders. from aqueous, water-suspendable or emulsion formulations; or usually as emulsions, aqueous suspensions or suspensions As will be readily appreciated, the antifungal properties of these compounds may be prepared from known liquids. As long as the desired utility is achieved without significantly impairing the activity of these compounds as therapeutic agents, Any material to which may be added may be used.

[0032] Wettable powders that can be compressed to form wettable granules contain one or more compounds of formula I, It comprises an intimate mixture of an active carrier and a surfactant. The concentration of the compound in the wettable powder is From about 10 weight percent to about 90 weight percent, more preferably from about 2 In preparing the wettable powder formulation, the compound may be present in an amount of from about 5 percent to about 75 percent by weight. The materials are pyrophyllite, talc, chalk, gypsum, fuller's earth, and beryllium. tonite, attapulgite, starch, casein, gluten, montmorillonite clay In such an operation, the mixture may be blended with any finely divided solid such as diatomaceous earth, refined silicates, etc. The finely divided carriers and surfactants are typically blended with the compound and milled.

[0033] The emulsion may contain from about 1 weight percent to about 50 weight percent of the compound of formula I, based on the total weight of the emulsion. The compound may be contained in a suitable liquid at a convenient concentration, such as centimeters. 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 those derived from petroleum aromatics, such as heavy aromatic naphtha, especially the high boiling naphthalenes. and olefinic moieties. Other organic solvents, such as terpene solvents, including rosin derivatives. , aliphatic ketones such as cyclohexanone, and alcohol complexes such as 2-ethoxyethanol You can also use your body.

[0034] Emulsifiers that may be advantageously used herein may be readily determined by one of skill in the art and may vary widely. Nonionic, anionic, cationic and amphoteric emulsifiers or blends of two or more emulsifiers Examples of non-ionic emulsifiers useful in preparing emulsions include polyalkylene glycols. Coal ethers, alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or Propylene glycol condensates of fatty acids and ethylene oxide, ethoxylated alkylphenols, etc. Polyols and polyoxyalkylenes solubilized carboxylic acid esters Cationic emulsifiers include quaternary ammonium compounds and fatty amines. Examples of anionic emulsifiers include oil-soluble salts of alkylarylsulfonic acids. (e.g. calcium), oil-soluble salts or sulfated polyglycol ethers and phosphated poly Suitable salts of glycol ethers are included.

[0035] Representative organic liquids that may be used to prepare emulsions of the compounds of the present disclosure include xylene, propyl Aromatic liquids such as benzene fractions; or mixed naphthalene fractions, mineral oils, dioctyl phthalate, etc. Any substituted aromatic organic liquids; kerosene; n-butyl ether of diethylene glycol, ethyl ether Various fatty acids such as ether or methyl ether of triethylene glycol, methyl ether of triethylene glycol Dialkylamides of acids, in particular the dimethylamides of fatty glycols and glycol derivatives, Oil, aromatic solvents, petroleum fractions or hydrocarbons such as paraffin oil; soybean oil, rapeseed oil, olive oil bean oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, parsley oil, Vegetable oils such as corn oil, peanut oil, safflower oil, sesame oil, and tung oil; A mixture of two or more organic liquids may be used to prepare the emulsion. The organic liquids may be: , xylene and propylbenzene fractions, with xylene being the most prevalent in some cases. Also preferred are surfactants, which are typically used in liquid formulations and contain a dispersant and one or more It is used in an amount of 0.1 to 20 weight percent based on the combined weight of the compound. The formulation may be used in combination with other compatible additives, such as plant growth regulators and other bioactive agents used in agriculture. The composition may also contain biologically active compounds.

[0036] The aqueous suspension may be at a concentration ranging from about 1 to about 50 weight percent based on the total weight of the aqueous suspension. At least one suspension of the water-insoluble compounds of formula I dispersed in an aqueous vehicle. Suspensions are prepared by finely grinding one or more compounds and then dissolving the ground material in water and the same suspensions as discussed above. The mixture is prepared by vigorously mixing with a vehicle composed of a surfactant selected from the same type. Other ingredients such as inorganic salts and synthetic or natural gums also affect the density and viscosity of the aqueous vehicle. It can be added to increase

[0037] The compounds of formula I may also be applied as granular formulations, which are particularly useful for application to the soil. Granule formulations are generally used in an amount of about 0.5 to about 10 parts by weight based on the total weight of the granule formulation. The compound is then mixed with attapulgite, bentonite, diatomaceous earth, clay or similar inexpensive material. The inert carrier is composed entirely or predominantly of coarsely divided inert material such as a Such a formulation usually contains the compound dissolved in a suitable solvent and diluted with about 0.5 to about It is prepared by application to a granular carrier preformed to a suitable particle size in the range of 3 mm. A suitable solvent is one in which the compound is substantially or completely soluble. Such a formulation may include A dough or paste of the carrier, compound and solvent is made, crushed and dried to produce the desired granular particles. It can also be prepared by obtaining

[0038] Dusts containing a compound of formula I may be prepared by incorporating one or more compounds in powder form, for example, kaolin clay, It may be prepared by intimately mixing with a suitable pulverulent agricultural carrier, such as crushed volcanic rock. Preferably, the powder contains about 1 to about 10 weight percent of the compound based on the total weight of the powder. It is possible.

[0039] The formulation may additionally contain a co-surfactant to aid in the adhesion, wetting and / or application of the compound to target crops and organisms. These co-surfactants may optionally be incorporated as components of the formulation or in the tank. The amount of co-surfactant is typically based on the amount of water applied. Generally, the amount is 0.01 to 1.0 volume percent, and preferably 0.05 to 0.5 volume percent. Suitable co-surfactants include ethoxylated nonylphenol, ethoxylated Synthetic or natural alcohol, salt of ester or sulfosuccinic acid, ethoxylated organic silicone , ethoxylated fatty amines, surfactant and mineral or vegetable oil blends, crop oil concentrates ( Mineral oil (85%) + emulsifier (15%); nonylphenol ethoxylate; benzyl core Alkyldimethyl quaternary ammonium salts; petroleum hydrocarbons, alkyl esters, organic acids and a Anionic surfactant blend; C9-C 11 Alkyl polyglycosides; Alkyl phosphate Alcohol ethoxylates; Natural primary alcohols (C 12 ~C 16 ) Ethoxylate; di-s ec-Butylphenol EO-PO block copolymer; Polysiloxane-methyl cap Nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl arsenic Coal (synthetic) ethoxylate (8EO); Tallow amine ethoxylate (15EO); P Formulations include, but are not limited to, EG(400) dioleate-99. Oil-in-water types, such as those disclosed in U.S. Patent Application Publication No. 11 / 495,228 Emulsifiers may also be included, the disclosure of which is expressly incorporated herein by reference.

[0040] The formulation may optionally include combinations containing other pesticidal compounds. Such additional pesticidal compounds may be combined with the compounds of the present disclosure in the medium selected for application. Fungicides, insecticides, herbicides and nematicides which are compatible and do not antagonize the activity of the compounds of the present invention , acaricides, arthropodicides, fungicides or combinations thereof. In such embodiments, the other pesticidal compound may have the same or a different pesticidal application. The compounds of formula I and pesticidal compounds in combination are used as supplemental toxicants in The materials may generally be present in a weight ratio of 1:100 to 100:1.

[0041] The compounds of the present disclosure can be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure may be used in one or more applications to control a variety of undesirable diseases. It is often applied in conjunction with other fungicides listed above. When used in conjunction with other fungicides, The compounds claimed herein may be formulated with or mixed with other fungicides. It may be applied in combination with other fungicides or sequentially with other fungicides. The agents include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylpheno 8-Hydroxyquinoline sulfate, amethoctrazine, aminopyrifen, Misulbrom, Antimycin, Ampelomyces kiskaris quisqualis, Azaconazole, Bacillus subtilis s subtilis, Bacillus subtilis s) Strain QST713, Benalaxyl, Benomyl, Benthalbaricarb Isopropyl, Be Benzobindiflupyr, benzylaminobenzenesulfonic acid (BABS) salt, bicarbonate, Biphenyl, bismerthiazole, bitertanol, bixafen, blasticidin- S, borax, Bordeaux mixture, boscalid, bromuconazole, buprimate, calcium polysulfide Um, Captafol, Captan, Carbendazim, Carboxin, Capropamide, Carbo Chloron, chlazafenone, chloroneb, chlorothalonil, chloro Zolinate, Coniothyrium minitans s), copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide , Cyazofamid, Cyflufenamid, Cymoxanil, Cyproconazole, Cyprodinil , Dazomet, Debacarb, Diammonium ethylenebis(dithiocarbamate), Diammonium Lofluanid, Dichlorophen, Diclocymet, Diclomedine, Dicloran, Diethf Encarb, difenoconazole, difenzoquat ion, diflumetrim, dimeth Morph, Dimoxystrobin, Diniconazole, Diniconazole-M, Dibuton, Dino Cup, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine Free base, edifenphos, enestrobin, enestrobulin, epoxiconazole, Ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, Fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fen Fentin, Fentin Acetate, Fentin Hydroxide, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluindapyr, Flumorph, Fluopicolide, Fluopyram, Flu Olomid, Fluoxapiproline, Fluoxastrobin, Fluquinconazole, Flu Silazole, Flusulfamide, Flutianil, Flutolanil, Flutriafol, Flu Xapyroxad, Folpet, Formaldehyde, Fosetyl, Fosetyl Aluminum, F Veridazole, Furalaxyl, Furametpyr, Guazatine, Guazatine Acetate, GY -81, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imazalil Zalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate ate, iminoctadine tris (albesilate), impilfluxam, iodocarb, Ipconazole, ipfenpyrazolone, iprobe Nphos, Iprodione, Iprovalicarb, Isofetamide, Isoflucipram, Isopro Lothiolane, Isopyrazam, Isotianil, Kasugamycin, Kasugamycin hydrochloride hydrate , kresoxim methyl, laminarin, mancopper, mancozeb, mandipropamide, Maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, dichlorodiphenyl ether Mercuric Dioxide, Mercuric Oxide, Mercuric Chloride, Metalaxyl, Metalaxyl-M, Metam, Metam-A ammonium, metam potassium, metam sodium, metconazole, metasulfocarb, Methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafe Non, Mildiomycin, Myclobutanil, Nabam, Nitroisopropyl, Nuari Mol, Octilinone, Ofurace, Oleic acid (fatty acid), Orysastrobin, Oxadix Sil, oxathiapiproline, oxine copper, oxpoconazole fumarate, oxycarbohydrate Voxin, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentak Chlorophenol, Pentachlorophenol Laurate, Penthiopyrad, Phenyl Acetate Water Silver, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxin, poly Oxolim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, Rochloraz, Procymidone, Propamocarb, Propamocarb hydrochloride, Propiconazole , propineb, proquinazid, prothioconazole, pydiflumetofen, pirametost Robin, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, Ribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyrrophenone Quiron, Quinoclamine, Quinoxyfen, Quintozene, Raynautria sakarinensis (Reynoutria sachalinensis) Extract, Sedaxane, Silthio Fam, Simeconazole, Sodium 2-Phenylphenoxide, Sodium Bicarbonate, Na Thorium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar Oil, tebuconazole, tebufloquine, tecnazene, tetraconazole, thiabendazole , thifluzamide, thiophanate methyl, thiram, tiadinil, tolclofos methyl, Rilfluanid, triadimefon, triadimenol, triazoxide, tricyclazol triflumizole, triforine, triticol, tridemorph, trifloxystrobin, triflumizole, triforine, triticol Nazole, validamycin, valifenalate, valifenal, vinclozolin, ginez B, Ziram, Zoxamide, Candida oleophila a), Fusarium oxysporum, Grigio Gliocladium species, Phlebiopsis gigantea opsis gigantea), Streptomyces griseoviridis (Strept omyces griseoviridis, Trichoderma ) species, (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide 1,2-Dichloropropane, 1,3-Dichloro-1,1,3,3-tetrafluoroethylene Oroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitro 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 3-Dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2 -Methoxyethylmercury acetate, 2-Methoxyethylmercury chloride, 2-Methoxyethyl mercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitrophenyl)- tropop-1-enyl)phenylthiocyanate, ampropylphos, anilazine, a Dithiram, Barium Polysulfide, Bayer 32394, Benodani, Benkinon benzamacryl isobutyl, benzam ... Pacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium Mium Calcium Copper Zinc Chromate Sulfate, Carbamorph, CECA, Chlobenzyl Azone, chloraniformethane, chlorphenazole, chlorquinox, climbazole , Copper bis(3-phenylsalicylate), Copper zinc chromate, Cumonoxystrobin, Kufra Neb, cupric hydrazinium sulfate, cuprobam, cyclafuramide, Cipendazole, cyproflam, decaphentin, diclobenthiazox, dicloron, di Chlozolin, diclobutrazol, dimethirimol, dinokton, dinosulfone, dinote Rubon, Dipimethitron, Dipyrithione, Ditalinphos, Dodizin, Drazoxolone, E BP, enoxastrobin, ESBP, etaconazole, etem, etilim (ethirim), phenaminestrobin, fenaminosulf, fenapanil, phenytoin Tropane, Fenpicoxamide, Florylpicoxamide, Flufenoxystrobin, F Luopimomide, Fluorotrimazole, Flucarbanil, Fluconazole, Fluconazole Lucis, Flumesiclox, Furofanart, Gliodin, Griseofulvin, Hara Clinart, Hercules 3944, Hexylthiophos, ICIA0858, Ip Fentrifluconazole, ipflufenoquin, isopamphos ), isovalerion, mandestrobin, mebenil, mecarbinzide, mefentriflul Conazole, methazoxolone, metofloxacin, methylmercuric dicyandiamide, methotrexate Hobax, Methyltetraprole, Milneb, Mucochloranhydride, Mikrozolin, N -3,5-Dichlorophenyl-succinimide, N-3-nitrophenylitaconimide , Natamycin, N-ethylmercurio-4-toluenesulfonanilide, Nickel bis (dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, Phenylmercuric nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarb Lid, pyrapropoin, pyridaclomethyl, pyridinitrile, pyrisoxazole, pyroxazole Ciclor, Piroxyflur, Quinaceto; Quinaceto sulfate, Quinazamide, Quinconazo , quinofumelin, rabenzazole, salicylanilide, SSF-109, sultrope , tecolam, thiadifluor, thiophene, thiochlorfenphim, thiophane thioquinox, tioximide, triamiphos, triarimol, triazbutyl , triclamid, triclopyricarb, triflumezopyrim, urbaci d), zaliramide, and any combination thereof.

[0042] In addition, the compounds described herein can be used in the medium of choice for application. Insecticides, nematicides, etc., which are compatible with the disclosed compounds and do not antagonize the activity of the compounds of the present invention. In combination with other pesticides, including acaricides, arthropodicides, fungicides or combinations thereof The fungicidal compounds of the present disclosure may be combined to form pesticidal mixtures and synergistic mixtures thereof. The product may be used in conjunction with one or more other pesticides to control a variety of undesirable pests. When used in conjunction with other pesticides, the compounds claimed herein may be Formulating the product with other pesticides, tank-mixing it with other pesticides, or It can be applied consecutively to other pesticides. Typical pesticides include 1,2-diphenylmethane, Chloropropane, Abamectin, Acephate, Acetamiprid, Acethione, Acetop rol, acrinathrin, acrylonitrile, acinonapyr, afidopiropen, arani Carb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, a Lixicarb, alpha-cypermethrin, alpha-ecdysone, alpha-endos Lufan, Amidithione, Aminocarb, Amiton, Amiton Oxalate, Amitraz, Nabasin, Atidathion, Azadirachtin, Azamethiphos, Azinphos-ethyl, Azinphos Smethyl, azotoate, barium hexafluorosilicate, bartholin, bendiocarb , Benfuracarb, Bensultap, Benzpyrimoxane, Beta-Cyfluthrin, Beta Tercypermethrin, bifenthrin, bioallenthrin, bioethanomethrin, biope Lumetrin, bistrifluron, borax, boric acid, broflanilide, bromfenbinfo Bromocycline, Bromo-DDT, Bromophos, Bromophos-ethyl, Buphen Carb, buprofezin, butacarb, butathiophos, butocarboxim, butonate, Butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide, chlorinated camphor carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbofuran Enothione, carbosulfan, cartap, cartap hydrochloride, chlorantranilipro chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform ruthenium hydrochloride, chloroethoxyphos, chlorfenapyr, chlorfenvinphos, chlor Fluazuron, chlormephos, chloroform, chloropicrin, chloroprallethrin, Chlorphoxim, Chlorprazophos, Chlorpyrifos, Chlorpyrifos-methyl, Lorthiophos, chromafenozide, cinerin I, cinerin II, cinerins, cysmetidine Phosphorus, cloethocarb, closantel, clothianidin, copper acetoarsenite, copper arsenate, naphtha Copper oleate, copper oleate, coumaphos, coumitoate, crotamiton, crotoxyphos, Sulfate, cryolite, cyanofenphos, cyanophos, cyanate, cyanthrani Liprole, cyclaniliprole, ciclethrin, cycloprothrin, cyfluthrin, cy Halodiamide, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, cythioa DDT, decarbofuran, deltamethrin, demephion, demephion-O, demephion-1, demephion-2 Mefion-S, Demeton, Demeton-Methyl, Demeton-O, Demeton-O-Methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methylsulfone, Diafenthiu Ron, Dialifos, Diatomaceous Earth, Diazinon, Dicapton, Diclofenthion, Diclofenthion Ruvos, dichloromethiazide, dicresyl, dicrotophos, dicyclanil, dieldrin , Diflubenzuron, Dirol, Dimefluthrin, Dimefox, Dimethane, Dimethoate To, Dimethrine, Dimethylvinphos, Dimethylan, Zinex, Zinex Diclex dioxabenzophos, dinoprop, dinosam, dinotefuran, diofenolan, dioxabenzophos, di Oxacarb, dioxathion, disulfoton, dicyclophos, d-limonene, DNOC , DNOC-ammonium, DNOC-potassium, DNOC-sodium, doramectin , ecdysterone, emamectin, emamectin benzoate, EMPC, empenthrin, Endosulfan, Endothion, Endrin, EPN, epofenonane, eprinomec Chin, Epsilon-Metofluthrin, Epsilon-Monfluorothrin, Esdeparethri , esfenvalerate, ethaphos, ethiofencarb, ethion, ethiprole, Ethoate-methyl, Ethoprophos, Ethylformate, Ethyl-DDD, Ethylenedibutyrate Romide, ethylene dichloride, ethylene oxide, etofenprox, etrimphos , EXD, Famfur, Fenamiphos, Fenazaflor, Fenchlorphos, Feneta Carb, fenfluthrin, fenitrothion, fenobucarb, fenoxacrim, Fenoxycarb, Fenpyrithrin, Fenpropathrin, Fensulfothion, Fen Fenthion, Fenthion-ethyl, Fenvalerate, Fipronil, Flomethoquin, Flomethoquin Nikamide, fluazaindolizine, flubendiamide, flucofuron, flucycloxro Flucythrinate, Fluensulfone, Flufenerim, Flufenoxuron, Flu Fenprox, Flufiprole, Fluhexafon, Flupyradifurone, Flupirimi fluvalinate, fluxametamide, fonophos, formetanate, formetanane Formparanate hydrochloride, Formothione, Formparanate, Formparanate hydrochloride, Fosmetiran, Hospirate, Hostetin, Furathiocarb, Frethrin, Gamma-Cyhalothrin, Ga HCH, Halfenprox, Halofenozide, HCH, HEOD, Heptaclo Heptafluthrin, Heptenphos, Heterofos, Hexaflumuron, HHDN, Hyd Lamethylnon, Hydrogen cyanide, Hydroprene, Hikicarb, Imidacloprid, Imip Lothrin, Indoxacarb, Iodomethane, IPSP, Isazophos, Isobenzane, I Socarbophos, Isocycloceram, Isodrin, Isofenphos, Isofenphos-methy Isoprocarb, Isoprothiolane, Isothioate, Isoxathion, Ivermec Chin, Jasmolin I, Jasmolin II, Iodofenphos, Juvenile Hormone I, Juvenile Hormone Mon II, Juvenile Hormone III, kappa-bifenthrin, kappa-tefluthrin, Kere Ban, Kinoprene, Lambda-Cyhalothrin, Lead Arsenate, Lepimectin, Leptophos, Linda , lilimfos, lufenuron, ritidathion, malathion, malonoven, magidox , mecarbam, mecarbone, menazone, meperfluthrin, mephosphoran, mercurous chloride , Mesulfenphos, Metaflumizone, Methacrifos, Methamidophos, Methidathion, Meth Thiocarb, methoclotophos, methomyl, methoprene, methoxychlor, methoxypheno methyl bromide, methyl isothiocyanate, methyl chloroform, methylene chloroform Lido, Metofluthrin, Metolcarb, Metoxadiazone, Mevinphos, Mexacarb Milbemectin, Milbemycin oxime, Mipafox, Mirex, Morosulta molosurup, monfluorotrin, monocrotophos, monomethypo, Monosultap, morphothion, moxidectin, naphthalophos, naled, naphthalene, Nicotine, Nifluridide, Nitenpyram, Nithiazine, Nitrilacarb, Novaluron, Biflumuron, omethoate, oxamyl, oxazosulfil, oxydemeton-methy , oxydeprophos, oxydisulfoton, para-dichlorobenzene, parathion, Lathion-methyl, Penfluron, Pentachlorophenol, Permethrin, Fencap Ton, fenothrin, phenthoate, phorate, phosalone, phospholane, phosmet, Phosnichlor, Phosphamidon, Phosphine, Phoxim, Phoxim-methyl, Pyrimethapho arsenite, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassium arsenite, thiocyanate Potassium anhydride, pp'-DDT, prallethrin, precocene I, precocene II, precocene Cosene III, Primidophos, Profenofos, Profluthrin, Promacyl, Promeca Lub, Propafos, Propetamphos, Propoxur, Protidathion, Prothiofos, Pro Rotoate, Protrifenbut, Piflubumid, Pyraclofos, Pyrafluprole, Pi Lazophos, Pyresmethrin, Pyrethrin I, Pyrethrin II, Pyrethrin, Pyridaben, Pyridalyl, Pyradaphenthion, Pyrifluquinazon, Pyrimidifen, Pyriminostro Bin, Pirimitate, Pyriprole, Pyriproxyfen, Cassia, Quinalphos, Quinal Phos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Riania, Sabadi La, Schraderdan, Selamectin, Silafluofen, Silica Gel, Sodium Arsenite, Sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sofa Mido, spinetoram, spinosad, spiromesifen, spiropydione, spirotetramer Sulfuron, Sulfuron-sodium, Sulfuramide, Sulfotep, Sulfox Safrol, Sulfuryl Fluoride, Sulprofos, Tau-Fulvalinate, Tazimcarb, T DE, tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, teflu Torin, Temephos, TEPP, Teralethrin, Terbufos, Tetrachlorantranilipro tetrachloroethane, tetrachlorovinphos, tetramethrin, tetramethylfluor Trimethrin, Tetraniliprole, Theta-Cypermethrin, Thiacloprid, Thiamethoxa cyclophos, thiocarboxim, thiocyclam, thiocyclam oxalate, thiodicar bu, thiofanox, thiometon, thiosultap, thiosultap-disodium, Thiosultap-monosodium, thuringiensin, thioxazafen, tolfenpi Rad, tralomethrin, transfluthrin, transpermethrin, trialasene, Riazamate, triazophos, trichlorfon, trichlormethaphos-3, trichlor Triflumezopyrim, Triflumuron, Trimethacarb, Trifenofos, ... Prene, Cyclopyrazoflor, Vamidothion, Vaniliprole, XMC, Xylylcarb , zeta-cypermethrin, zolaprophos and any combination thereof. The present invention is not limited to these.

[0043] In addition, the compounds described herein can be used in the medium of choice for application. in combination with herbicides that are compatible with the disclosed compounds and do not antagonize the activity of the compounds of the present invention; The fungicidal compounds of the present disclosure may form pesticidal mixtures and synergistic mixtures thereof. It may be applied in conjunction with one or more other herbicides to control unwanted vegetation. When used in conjunction with, the compounds claimed herein may be formulated with or used as herbicides. It can be tank mixed with the herbicide or applied sequentially with the herbicide. As for the 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-T BA; 2,4,5-T; 2,4,5-TB; Acetochlor, acifluorfen, acyl Ronifen, acrolein, alachlor, aridochlor, alloxydim, allylal Cole, Arolac, Ametridione, Ametrine, Amivudine, Amicarbazone, Ami Dosulfuron, aminocyclopyrachlor, aminopyralid, amiprophosmethyl, ami Trol, Ammonium Sulfamate, Anilofos, Anisrone, Ashram, Atla Ton, Atrazine, Azaphenidine, Azimsulfuron, Aziprothrin, Burban, B CPC, beflubutamide, beflubutamide-M, benazolin, bencarbazone, benflu Larin, Benfuresate, Bensulfuron, Bensulide, Bentazon, Benzadox, Be Nzfendizon, Benzipram, Benzobicyclon, Benzofenap, Benzofluo benzoylprop, benzthiazuron, bicyclopyrone, bifenox, virane Phos, Bispyribac, Bixlozone, Borax, Bromacil, Bromobonyl, Bromo Butid, bromofenoxime, bromoxynil, brompyrazone, butachlor, butaf Butenacil, Butamifos, Butenachlor, Butidazole, Buthiuron, Butralin, Buto Roxydim, Buturon, Butyrate, Cacodylic Acid, Cafenstrole, Calcium Chlorate Calcium cyanamide, Cambendichlor, Carbaslam, Carbetamide, Carboxylic Acid Sasol chlorprocarb, carfentrazone, CDEA, CEPC, chlormethoxyf phenanthrene, chloramben, chloranocryl, chloradifop, chlorazine, chlorbromuron , Chlorbufam, Chloreturon, Chlorfenac, Chlorfenprop, Chlorf Lurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, Chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, Lorsulfuron, Chlorthal, Chlorthiamid, Cinidon Ethyl, Cinmethylin, Cino Sulfuron, cisanilide, clasifos, clethodim, clodinate, clodinafop , Clofop, Clomazone, Clomeprop, Cloprop, Cloproxyzim, Clopi Ralido, chloransulam methyl, CMA, copper sulfate, CPMF, CPPC, Cledazin, Resole, cumyluron, cyanatrin, cyanazine, cycloate, cyclopyranyl, Chlopirimorate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop , Cypercort, Cyprazine, Cyprazole, Cypromid, Dimron, Dalapon, Dalapon Zomet, Delachlor, Desmedipham, Desmetrin, Diallate, Dicamba, Di Chlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop -P, diclofop, diclosulam, diethamcoat, diethathyl, diphenopentene, Difenoxuron, Difenzocort, Diflufenican, Diflufenzopyr, Zimef Ron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid -P, Dimexano, Dimidazon, Dinitramine, Dinophenate, Dinoprop, Ginosa , dinoseb, dinoterb, diphenamide, dipropetrine, diquat, disulf, dithi Ophir, Diuron, DMPA, DNOC, DSMA, EBEP, Eglinadin, Endota ol, epronaz, EPTC, elbon, esprocarb, ethalfluralin, ethamet Lufron, Ethidimuron, Ethiolate, Ethofumesate, Ethoxyphene, Ethoxys Lufron, Ethinofen, Etonipromide, Etobenzanide, EXD, Fenashlam, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxasulfone, Fenquinotrione, Fenteracol, Fenthiaprop, Fentrazamide, Fent Nuron, Ferrous Sulfate, Flamprop, Flamprop-M, Flazasulfuron, Floras Ram, Florpyrauxifen, Fluazifop, Fluazifop-P, Fluazolate , Flucarbazone, Flucetosulfuron, Fluchloralin, Flufenacet, Flufe Nikan, Flufenpyr, Flumetsulam, Flumezin, Flumiclorac, Flumioxa djin, flumipropine, fluometuron, fluorodifen, fluoroglycofen, Luoromidine, Fluoronitrofen, Fluothiuron, Flupoxam, Flupropacil , Flupropanate, Flupyrsulfuron, Fluridone, Flurochloridone, Fluroxy Pill, Flutamon, Fluthiaset, Fomesafen, Foramsulfuron, Hosamine, Fu Riloxifene, Glufosinate, Glufosinate-P, Glyphosate, Haloxifene , Halosafen, Halosulfuron, Haloxydine, Haloxyfop, Haloxyfop-P , Hexachloroacetone, Hexaflurate, Hexazinone, Imazamethabenz, Imaza Mox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Indanofan, Indaziflam, Iodobornyl, Iodomethane, Iodosulfuron, I Ofensulfuron, Ioxynil, Ipazine, Ipfencarbazone, Iprimidam , Isocarbamide, Isosyl, Isomethiozine, Isonorurone, Isopolynate, Isopropanol Loparin, isoproturon, isouron, isoxaben, isoxachlorthor, isoxacillin Saflutol, Isoxapirifopp, Carbutilate, Ketospiradox, Rancotri On, Lactofen, Lenacil, Linuron, MAA, MAMA, MCPA, MCPA- Thioethyl, MCPB, Mecoprop, Mecoprop-P, Medinoterb, Mefenacet mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifo p, metamitron, metazachlor, metazosulfuron, metofluran, methabenzthi Azulon, Methaproparin, Methazole, Methiobencarb, Methiozoline, Methiouro Methameton, meprothrin, methyl bromide, methyl isothiocyanate, methyl dimethicone Muron, Methobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron , metribuzin, metsulfuron, molinate, monalid, monisouron, monochloroacetic acid acid, monolinuron, monuron, morphamcoat, MSMA, naproanilide, naphthyl Lopamide, Napropamide-M, Naptalam, Nebulon, Nicosulfuron, Nipiraclofe Nitralin, Nitrofen, Nitrofluorfen, Norflurazon, Norlon, O CH, Orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin , oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziq Lomefon, oxyfluorfen, parafluron, paraquat, pebulate, pelargon Acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pen Toxazone, Perfluidon, Petoxamide, Phenisopham, Phenmedipham, Phenmedipham ethyl, Fenobenzuron, Phenylmercuric acetate, Picloram, Picolinic acid Naphen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate um, pretilachlor, primisulfuron, procyazin, prodiamine, proflua Zole, Profluralin, Profoxydim, Proglinadin, Prometon, Prometryn , Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propiso Chlor, Propoxycarbazone, Propyrisulfuron, Propyzamide, Prosulfari Prosulfocarb, Prosulfuron, Proxan, Prinachlor, Pidanone, Pyrac Ronil, Pyraflufen, Pyrasulfotole, Pyrazolinate, Pyrazosulfuron, Pyra Zoxifen, pyribenzoxim, pyributicarb, pyrichlor, pyridafol, pyride ate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxas Luhon, piroxulam, quinclorac, quinmerac, quinoclamine, quinonamide, Quizalofop, Quizalofop-P, Rhodetanil, Rimsulfuron, Saflufenacil, S -Metolachlor, Sebutylazine, Secubumeton, Sethoxydim, Siduron, Simazine , Simeton, Simetryne, SMA, Sodium arsenite, Sodium azide, Sodium chlorate um, sulcotrione, sulfarate, sulfentrazone, sulfometuron, sulfo Sulfuron, Sulfuric acid, Surglicapin, Swep, TCA, Tebutam, Tebuthiuron, Tebutam Furiltrione, tembotrione, tepraloxydim, terbacil, terbucarb, ter Buchlor, Terbumeton, Terbuthylazine, Terbutryn, Tetrafluron, Thenylchlor thiazafflurone, thiazopyr, thidiazamine, thidiazuron, thiencarbazonone Thiol, Thifensulfuron, Thiobencarb, Thiafenacil, Thiocarbazil, Thioc Lorim, torpiralate, topramezone, tralkoxydim, triafamone, triare , triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Trifludimoxazine, Trif Luralin, Triflusulfuron, Trihop, Trifopsim, Trihydroxytriazine , trimeturon, tripropindan, tritac, tritosulfuron, vernolate and These include, but are not limited to, xylachlor.

[0044] In another embodiment of the invention, Formula 1 is It may be used in combination with one or more other active ingredients such as those mentioned above (or in sequential applications). do.

[0045] In another embodiment of the invention, Formula 1 is a compound having the same, similar or preferred MoA as Formula 1, respectively. or one or more active ingredients with different mechanisms of action (MoA) (e.g., compositional mixtures) The compositions may be used in combination (in a single product or in simultaneous or sequential application).

[0046] In another embodiment, Formula 1 has acaricidal, algaecidal, avicidal, bactericidal, fungicidal properties. , herbicidal properties, insecticidal properties, molluscicidal properties, nematicidal properties, rodenticidal properties and / or viricidal properties One or more molecules having the properties can be used in combination with (e.g., in a compositional mixture or simultaneously or sequentially in an application).

[0047] In another embodiment, Formula 1 is an anorectic agent, a bird repellent, a chemical sterilant, a herbicide toxicity mitigator, an insect attractant, an insect repellent, a mammalian repellent, a mating inhibitor, a plant activator, a plant growth regulator , a plant health stimulant or promoter, a nitrification inhibitor and / or a synergist, and one or more molecules (e.g., in a compositional mixture or simultaneously or sequentially in an application) can be used in combination.

[0048] In another embodiment, Formula 1 can be used in combination with one or more biopesticides (e.g., in a compositional mixture or simultaneously or sequentially in an application).

[0049] In another embodiment, the combination of Formula 1 and the active ingredient in the biocidal composition can be used in various weight ratios. For example, in a two-component mixture, as the weight ratio of Formula 1 to the active ingredient, the weight ratios in TABLE1 can be used. However, generally, the weight ratio is preferably from about 1 0:1 to less than about 1:10.

[0050]

Table 1A

[0051] The weight ratio of the molecule of Formula 1 to the active ingredient can also be expressed as X:Y (where X is the part by weight of Formula 1 and Y is the part by weight of the active ingredient). The numerical range of the part by weight of X is 0 < X ≦ 100, and the part by weight of Y is 0 < Y ≦ 100, as shown in TABLE2 It is shown in the table. By way of non-limiting example, the weight ratio of Formula 1 to the active ingredient is 20:1 obtained.

[0052]

Table 1B

[0053] The range of the weight ratio of Formula I to the active ingredient can be expressed as X1:Y1~X2:Y2, where X and Y are defined above.

[0054] In one embodiment, the range of the weight ratio can be X1:Y1~X2:Y2, where X1> Y1 and X2<Y2. By way of non-limiting example, the range of the weight ratio of Formula 1 to the active ingredient can be 3:1~1:3 (including both ends).

[0055] In another embodiment, the range of the weight ratio can be X1:Y1~X2:Y2, where X1 >Y1 and X2>Y2. By way of non-limiting example, the range of the weight ratio of Formula 1 to the active ingredient can be 15:1~3:1 (including both ends).

[0056] In another embodiment, the range of the weight ratio can be X1:Y1~X2:Y2, where X1 <Y1 and X2<Y2. By way of non-limiting example, the range of the weight ratio of Formula 1 to the active ingredient can be about 1:3~about 1:20 (including both ends).

[0057] 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 (for example, applying to cereal or grape vines ). The compounds show low phytotoxicity while treating a variety of plants at fungicidal levels The compounds are useful in both protectant and / or eradicant modes. It is possible.

[0058] The compounds have been found to have significant fungicidal activity, especially in agricultural applications. Many of the compositions are particularly useful for use on agricultural and horticultural plants.

[0059] The efficacy of the compounds against the aforementioned fungi establishes their general utility as fungicides. It will be understood by those skilled in the art that

[0060] The compounds have a broad range of activity against fungal pathogens. Exemplary pathogens include Com. Zymoseptoria tritici (Zymoseptoria tritici) , Wheat leaf rust (Puccinia triticina) ), wheat stripe rust (Puccinia striiformis ormis), apple scab (Venturia inaequalis inaequalis), Grape powdery mildew (Uncinula necator la necator), barley scald (Rhyn chosporium commune), rice blast disease (Magnaporthe grisea (Magnaporthe grisea), soybean rust (Phakopsora pachyrifolia) Phakopsora pachyrhizi), wheat gall rot (parastaphylococcus aureus) Parastagonospora nodorum, com Powdery mildew of oak (Blumeria graminis var. tritici) inis f.sp.tritici), powdery mildew of barley (Brumeria gourami) Blumeria graminis f.sp.hordei ), powdery mildew of Cucurbitaceae plants (Erysiphe cicolarum horacearum), anthracnose of cucurbits (Glomerella lagenarium (Glom erella lagenarium), leaf spot disease of spinach (Cercospora beticola Cercospora beticola), tomato late blight (Alternaria solani (Alternaria solani), barley spot (Cochliobolus Cochliobolus sativus) and net blotch of barley (Piperus sativus) The pathogen Pyrenophora teres may be mentioned. The exact amount of active material applied will depend on the particular active material being applied. In addition to the agent, the specific action desired, the species of fungus to be controlled and its growth stage, and the compound It also depends on the part of the plant or other product with which it is contacted. and formulations containing it are equally effective at similar concentrations or against the same fungal species. There may not be.

[0061] The compounds are disease-suppressing and effective for application to plants in botanically acceptable amounts. The term "disease-inhibiting and botanically acceptable amount" refers to the amount of the plant disease that is desired to be controlled. This refers to the amount of a compound that will kill or inhibit the growth of bacteria but is not significantly toxic to plants. Generally, it is about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required will depend on the fungal disease being controlled, the type of formulation being used, and the application method. It varies depending on the method, the particular plant species, the climatic conditions, etc. Suitable application rates are typically: Approximately 0.10 to 4 pounds per acre (approximately 0.01 to 0.45 grams per square meter) , g / m 2 ) range.

[0062] Any ranges or desired values ​​presented herein may be varied without losing the effect sought. The present invention may be broadly expanded or modified in any manner that would be apparent to one of ordinary skill in the art having access to the teachings of this specification. .

[0063] The compounds of formula I can be made using well-known chemical procedures. Intermediates not included are either commercially available or can be made by routes disclosed in the chemical literature. or can be readily synthesized from commercially available starting materials using standard procedures. Either

[0064] General Scheme The following scheme illustrates a method for producing the aryl amidine compounds of formula (I). The following description and examples are offered by way of illustration and are not intended to be limiting with respect to substituents or substitution patterns. should not be construed as constituting a

[0065] A compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is as defined at the beginning Formula 1.2) can be prepared by the method shown in Scheme 1, steps a to c. (wherein R 2 , R 4 and R 5 is defined as the first step) is 1, step a. Compounds of formula 1.1, where R 2 , R 4 and R 5 is defined as the first) in N,N-dimethylformamide ( In the presence of iodine (I2) in a solvent such as DMF at temperatures between about 23°C and 50°C and treating with sodium periodate to give the compound of formula 1.2 (formula 1.3) as shown in a. Medium, R 2 , R 4 and R 5 is defined as initially. Compound 3 of formula R 2 , R 3 , R 4 and R 5 is defined as the first Compounds of formula 1.2 ( In the formula, R 2 , R 4 and R 5 is as defined initially), as shown in b As shown above, in a solvent such as 1,4-dioxane, cesium carbonate (Cs2CO3) in dichloromethane at temperatures between about 23°C and 120°C under microwave irradiation in the presence of a base of and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) Catalysts such as the complex (PdCl2(dppf)DCM) and B3O3R 3 3 (wherein, R 3 teeth, as initially defined) to give compounds of formula 1.3 ( In the formula, R 2 , R 3 , R 4 and R 5 is defined as the first The compound of formula 1.4 (wherein R 2 , R 3 , R 4 and R 5is defined as (which is a carboxylic acid) can be prepared by the method shown in Scheme 1, step c. Compound (wherein, R 2 , R 3 , R 4 and R 5 is defined as the first, As shown in the figure, 3:2:1 tetrahydrofuran ( Lithium hydroxide in a solvent mixture such as THF:methanol (MeOH):water (HO) By treatment with a base such as lithium (LiOH), a compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined as first. Scheme 1 [ka]

[0066] Alternatively, a compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined first can be prepared by the method shown in Scheme 2, steps d-f. Compounds of formula 2.2, where R 2 , R 4 and R 5 is defined as the first Compounds of formula 2.1 ( In the formula, R 2 , R 4 and R 5 is as defined initially), as shown in d in a solvent such as N,N-dimethylformamide (DMF) at temperatures between about 0°C and 23°C as follows: with a halogenating agent such as N-bromosuccinimide (NBS) to give formula 2. Compound 2 (wherein R 2 , R 4 and R 5 is as defined at the beginning) The compound of formula 2.3 (wherein R 2 , R 3 , R 4 and R 5 is first defined as (which is the case) can be prepared by the method shown in Scheme 2, step e. Compound 2, wherein R 2 , R 4 and R 5 is defined as the first, As shown in the figure, the reaction mixture is 10:1 1,4-dioxane:water at temperatures between about 23°C and 100°C. In the presence of a base such as potassium phosphate (K3PO4) in a solvent mixture such as -Dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (phenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate Catalysts such as sulfonate (XPhos-Pd-G3) and B3O3R 3 3 (wherein, R 3 teeth, as initially defined) to give compounds of formula 2.3 ( In the formula, R 2 , R 3 , R 4 and R 5 is defined as the first The compound of formula 1.4 (wherein R 2 , R 3 , R 4 and R 5 is defined as (which is a carboxylic acid) can be prepared by the method shown in Scheme 2, step f. Compound (wherein, R 2, R 3 , R 4 and R 5 is defined as the first, As shown in the figure, potassium hydroxide is easily dissolved in a solvent such as water at temperatures between about 23°C and 60°C. By treatment with a base such as potassium hydroxide (KOH), a compound of formula 1.4, 2 , R 3 , R 4 and R 5 is defined as first. Scheme 2 [ka]

[0067] Alternatively, a compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined first can be prepared by the method shown in Scheme 3, steps g-n. Compounds of formula 3.2, where R 2 , R 3 , R 4 and R 5 is as defined at the beginning The compound of formula 3.1 can be prepared by the method shown in Scheme 3, step g. compound (wherein, R 2 , R 3 , R 4 and R 5 is defined as the first, As shown in the figure, sodium nitrite is reacted with acetic acid or another solvent at temperatures between about 23°C and 85°C. Treatment with hydrogen bromide (HBr) in the presence of ammonium (NaNO2) affords the compound of formula 3.2 (In the formula, R 2 , R 3 , R 4 and R 5 is as defined at the beginning) The compound of formula 3.3 (wherein R 2 , R 3 , R 4 and R 5 is defined as (which is a carboxylic acid) can be prepared by the method shown in Scheme 3, step h. (wherein R 2 , R 3 , R 4 and R 5 is defined as the beginning), As shown in the figure, 1:1 ethanol (EtOH): Ammonium chloride (NH4Cl) in a solvent mixture such as H2O In the presence of salt, iron (Fe 0 ) to give compounds of formula 3.3, R 2 , R 3 , R 4 and R 5 is as defined at the beginning). Instead, a compound of formula 3.3, where R 2 , R 3 , R 4 and R 5 is first defined as (which is the same as above) can be prepared by the method shown in Scheme 3, step i. Formula 3. Compound 4 (wherein R 2 , R 3 , R 4 and R 5 is defined as the beginning), As shown in Fig. i, N,N-dimethylformamide (D In a solvent such as MF, halogenated reagents such as N-bromosuccinimide (NBS) are used. Upon treatment with a drug, a compound of formula 3.3, 2 , R 3 , R 4 and R 5 is defined first Compounds of formula 3.5 (wherein R 2 , R 3 , R 4 and R 5 is as defined initially) in the process shown in Scheme 3, step j Compounds of formula 3.3, where R 2 , R 3 , R 4 and R 5 First, (as defined above) is heated to about 100° C. under microwave irradiation as shown in j. At temperatures between 23℃ and 180℃ in solvents such as N-methyl-2-pyrrolidone (NMP) Treatment with a metal cyanide such as CuCN affords compounds of formula 3.5, where R 2 , R 3 , R 4 and R 5 is as originally defined. Alternatively, we can obtain (wherein R 2 , R 3 , R 4 and R 5 is defined as the first The compound of formula 3.3, wherein , R 2 , R 3 , R 4 and R 5 is defined as the beginning), denoted in k As shown in Fig. 1, tetrakis(trifluoromethyl)phenylacetamide is produced in a solvent such as DMF at temperatures between about 23°C and 120°C. In the presence of a metal catalyst such as phenylphosphine-palladium(0) (Pd(PPh3)4) In the reaction, zinc(II) cyanide (Zn(CN)2) is added to the reaction mixture to obtain the compound of formula 3.4, where R 2 , R 3 , R 4 and R 5is as defined at the beginning) Compounds of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined first (as defined above) can be prepared by the method shown in Scheme 3, step l. A compound of formula 3.5, where R 2 , R 3 , R 4 and R 5 is defined as (which is the compound represented by the formula (1)) in a solvent such as HO at a temperature of about 23 to 120° C. with a base such as potassium hydroxide (KOH) to give compounds of formula 1.4, 2 , R 3 , R 4 and R 5 is as defined initially). In addition, a compound of formula 3.6, 2 , R 3 , R 4 and R 5 is defined as (which is a carboxylic acid) can be prepared by the method shown in Scheme 3, step m. (wherein R 2 , R 3 , R 4 and R 5 is defined as the beginning), m As shown in the figure, methanol is heated at a pressure of about 400 psi and a temperature of about 23° C. to 125° C. In a solvent such as alcohol, 1,4-bis( In the presence of ligands such as diphenylphosphanylbutane, palladium(II) acetate, etc. with carbon monoxide (CO) gas in the presence of a metal catalyst of formula 3.6 Medium, R 2 , R 3 , R4 and R 5 is as defined initially) Compounds of formula 1.4, where R 2 , R 3 , R 4 and R 5 is as defined at the beginning The compound of formula 3.6 can be prepared by the method shown in Scheme 3, step n. compound (wherein, R 2 , R 3 , R 4 and R 5 is defined as the first, As shown in Fig. 1, the reaction mixture was 3:2:1 THF:MeOH:water at temperatures between about 23°C and 125°C. In any solvent mixture, treatment with a base such as lithium hydroxide (LiOH) produces the compound represented by formula 1.4. (wherein R 2 , R 3 , R 4 and R 5 is as defined initially) It is possible. Scheme 3 [ka]

[0068] A compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is first defined as (which is the same as above) can be prepared by the method shown in Scheme 4, step o. Formula 1. Compound 4 (wherein R 2 , R 3 , R 4 and R 5 is defined as the beginning), As shown in o, the reaction may be carried out in a solvent such as dichloromethane (DCM) at a temperature between about 0° C. and ambient temperature. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (ED CI), N,N'-dicyclohexylcarbodiimide (DCC) or benzotriazole -1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBO P) and dimethylaminopyridine (DMAP) or N- In the presence of a catalyst such as ethyl-N-isopropylpropan-2-amine (DIPEA), IteR 1 -OH(in the formula, R 1 is as defined initially) To this end, a compound of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is defined first Alternatively, a compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is as defined initially) in Scheme 4, step p Compounds of formula 1.4 (wherein R 2 , R 3 , R 4 Reach BiR 5 is as defined initially) at about 23° C., as shown in p. In a solvent such as DMF at room temperature, in the presence of a base such as potassium carbonate (K2CO3), IteR 1 -Br(wherein, R 1 is as defined initially, to give a compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5is defined first (as shown in FIG. 1) can be obtained. Scheme 4 [ka]

[0069] A compound of formula 5.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined first (as defined above) is prepared by the method shown in Scheme 5, step q. A compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is defined first As shown in q, the reaction is carried out in the presence of toluene or the like at a temperature of about 23°C to 90°C. In a solvent of 7 and R 8 is defined as ) to give compounds of formula 5.2, 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined as first. Scheme 5 [ka]

[0070] Alternatively, a compound of formula 5.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7and R 8 teeth , as initially defined), in the process shown in Scheme 6, steps r to s. Compounds of formula 6.1, where R 1 , R 2 , R 3 , R 4 and R 5 The most and Z is an alkyl group, Compounds of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is defined as the beginning), as shown in r, p-Toluenesulfonic acid monohydrate at a temperature of about reflux (about 100°C or about 140°C, respectively) In the presence of an acid catalyst such as (pTsOH-H2O), trimethyl orthoformate or Trialkyl orthoformates (CH(OZ)3), such as triethyl formate, where Z is an alkyl aryl group) to give compounds of formula 6.1, 1 , R 2 , R 3 , R 4 and R 5 teeth , as originally defined and Z is an alkyl group. A compound of formula 5.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined first (as shown in Scheme 6, step s) can be prepared by the method shown in Compounds of formula 6.1 (wherein R 1 , R 2 , R 3 , R 4and R 5 is first defined as and Z is an alkyl group, as shown in s, at about 23° C. to Compound 6.2 (wherein R 7 and R 8 teeth, as initially defined) to give compounds of formula 5.2, 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined initially) It is possible. Scheme 6 [ka]

[0071] A compound of formula 7.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 The most (as defined initially) can be prepared by the method shown in Scheme 7, step t. Compounds of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is previously defined (as shown in t) at a temperature of about 23° C. to reflux (about 110° C.). In the presence of a dehydrating agent such as phosphoryl trichloride (POCl3) in a solvent such as toluene at 37°C, In the presence of 6 , R 7 and R 8 is defined as to give compounds of formula 7.2, 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is defined as first. Scheme 7 [ka]

[0072] A compound of formula 8.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined first (as defined above) can be prepared by the method shown in Scheme 8, steps u to v. Compounds of formula 8.1, where R 1 , R 2 , R 3 , R 4 and R 5 is previously defined (as shown) can be prepared by the method shown in Scheme 8, step u. A compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is as previously defined. ) in 1:1 DCM:HO, etc. at a temperature of about 23° C., as shown in u. In the presence of a base such as sodium bicarbonate (NaHCO3) in a solvent mixture Treatment with thiophosgene gives compounds of formula 8.1, where R 1 , R 2 , R 3 , R 4 and R 5 teeth , as previously defined), can be obtained. 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined previously) is the scheme 8, step v. Compounds of formula 8.1, where R 1 , R 2 , R 3 , R 4 and R 5 is as previously defined), denoted in v Compounds of formula 6.2, where R 7 Reach BiR 8 is as defined initially) to give compounds of formula 8.2 (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined at the beginning ) can be obtained. Scheme 8 [ka]

[0073] Alternatively, a compound of formula 9.3, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 teeth , as initially defined), in the process shown in Scheme 9, steps w to x. Compounds of formula 9.1, where R 1 , R 2, R 3 , R 4 and R 5 The most (as defined initially) can be prepared by the method shown in Scheme 9, step w. Compounds of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5 is defined first (as shown in w) at a temperature of about reflux (about 100° C.) In the presence of an acid catalyst such as p-toluenesulfonic acid monohydrate (pTsOH-H2O) Treatment with trimethyl orthoformate gives compounds of formula 9.1, where R 1 , R 2 , R 3 , R 4 Reach BiR 5 is as defined initially). Compounds of formula 9.3 (formula 9.4) can be obtained. Medium, R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined at the beginning) Compounds of formula 9.1 can be prepared by the method shown in Scheme 9, step x. (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 is defined as the first, As shown in the figure, the reaction mixture was mixed in a 1:1 mixture of methanol and 1:1 at temperatures between about 23°C and reflux (about 80°C). In the presence of a base such as triethylamine in a solvent mixture such as 4-dioxane to produce a compound of formula 9.2, where R 7 and R 8 (is defined as the first) amine to give compounds of formula 9.3, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined as first. Scheme 9 [ka]

[0074] A compound of formula 10.2, where R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 First, (as defined above) is prepared by the method shown in Scheme 10, step y. Compounds of formula 10.1, where R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 teeth , as defined initially), at about 23° C. to 60° C., as indicated in y. Treat with a base such as sodium hydroxide (NaOH) in a solvent such as MeOH at room temperature. and forming a compound of formula 10.2, 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 First (as defined in Scheme 10 [ka]

[0075] A compound of formula 11.1, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 First, (as defined above) is prepared by the method shown in Scheme 11, step z. Compounds of formula 8.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 teeth, (as defined initially) is acetone at a temperature of about 23° C., as shown in In the presence of a base such as potassium carbonate (K2CO3) in a solvent such as toluene, and methane to give compounds of formula 11.1, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined as first. Scheme 11 [ka]

[0076] A compound of formula 12.1, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 First, (as defined above) can be prepared by the method shown in Scheme 12, step aa. Compounds of formula 5.2, where R 1 , R 2 , R 3 , R4 , R 5 , R 7 and R 8 teeth , as originally defined), at a temperature of about 23° C., as shown in aa. Hydrochloric acid (HCl), hydrobromic acid (HBr), Acetic acid (HOAc), trifluoroacetic acid, para-toluenesulfonic acid (pTsOH) or Treatment with a protic acid (HX), such as enoic acid, gives compounds of formula 12.1, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is defined as the first do. Scheme 12 [ka] EXAMPLES

[0077] Example 1A: Preparation of methyl 4-amino-5-iodo-methylbenzoate [ka] Methyl 4-amino-2-methylbenzoate (0.29 g, 1. 76 mmol) of sodium periodate (0.14 g, 0.70 mmol) ) and I2 (74 mg, 1.41 mmol) were added. The reaction mixture was stirred at 50° C. for 3 h. The reaction mixture was then diluted with saturated sodium thiosulfate solution (5 mL). The solid was then filtered. The crude product was triturated with EtOH (1 mL) and pentane (9 mL). Evaporation into water afforded the title compound (0.22 g, 43% yield) as a pink solid.1 HN MR(400MHz,CDCl3)δ 8.27(s,1H),6.54(s,1H), 4.38(brs,2H),3.84(s,3H),2.50(s,3H);ESIMS m / z 292([M+H] + ).

[0078] Example 1B: Preparation of methyl 4-acetamido-5-bromo-2-methoxybenzoate [ka] Methyl 4-acetamido-2-methoxybenzoate (4.04 g) in DMF (80 mL) To a solution of N-bromosuccinimide (3.22 g, 18.1 mmol), l) was added at 0° C. The mixture was stirred at 0° C. and allowed to warm slowly to room temperature with stirring overnight. The mixture was then diluted with water and a precipitate formed. The precipitate was filtered off and washed with additional water. The precipitate was dried under vacuum to give impure product. The crude product was purified by flash column chromatography. Chromatography (silica gel (SiO2), 0→100% ethyl acetate in hexane) This was purified to give the title compound (3.89 g, 12.9 mmol, 71% yield) as a white solid. ) was obtained. 1 H NMR(400MHz,CDCl3)δ 8.32(s,1H),8. 04(s,1H),7.76(s,1H),3.93(s,3H),3.87(s,3H ),2.28(s,3H); 13 C NMR (101 MHz, CDCl3) δ 166. 28,162.47,157.58,137.80,132.74,113.36,10 2.13,99.53,54.06,49.79,22.92;ESIMS m / z 3 04 [(M+H) + ].

[0079] Example 1C: Preparation of 4-bromo-5-methyl-2-(trifluoromethyl)aniline [ka] In a 25 mL vial, 5-methyl-2-(trifluoromethyl)aniline ( A solution of 1.00 g, 5.71 mmol) was prepared in DMF (18 mL). The reaction was cooled to ice. The mixture was cooled to 0° C. in a water bath. Next, N-bromosuccinimide (1.02 g, 5.71 m mol) was added in one portion. The reaction was stirred overnight and allowed to slowly come to ambient temperature to allow the ice to melt. After 18 h, the reaction was quenched with water (50 mL) and EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×50 mL). The organic layer was washed with brine (3×100 mL), dried over MgSO4, filtered and concentrated. to give the title compound (1.31 g, 5.16 mmol, 90% yield) as a dark yellow oil. This was used without further purification. 1 H NMR (400MHz, CDCl3) δ 7.54(s,1H),6.63(s,1H),4.09(s,2H),2.32(s ,3H); 19 F NMR(376MHz,CDCl3)δ -62.58;HRMS- ESI(m / z)[M+H] + Calculated value for C8H8BrF3N: 253.9787 ;Measured value: 253.9778.

[0080] Example 2A: Preparation of methyl 4-amino-2,5-dimethylbenzoate [ka] Methyl 4-amino-5-iodo-2-methylbenzoate in 1,4-dioxane (5 mL) A solution of 0.22 g, 0.75 mmol of cesium carbonate (0.98 g, 3.02 mmol) was ol) was added and it was degassed for 5 min. Then, PdCl2(dppf)DCM (0.06 1g, 0.07mmol) and trimethylboroxine (0.23g, 1.88mmol) The reaction mixture was heated to 120° C. under microwave irradiation for 1 hour. (15 mL) and extracted with EtOAc (2×40 mL). The combined organic layers were washed with anhydrous The mixture was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography. Chromatography (silica gel (SiO2), 20→25% ethyl acetate in hexane) This was purified by HPLC to give the title compound (0.11 g, 84% yield) as a brown solid. S m / z 180([M+H] + ).

[0081] Example 2B: Preparation of methyl 4-acetamido-2-methoxy-5-methylbenzoate [ka] Methyl 4-acetamido-5-bromo-2-methoxybenzoate (2.00 g, 6.62 mmol), methylboronic acid (0.594 g, 9.93 mmol), XPhosPd G 3 (0.112 g, 0.132 mmol) and potassium phosphate tribasic (2.81 g, 13.2 (mmol) dissolved / suspended in 1,4-dioxane (30.1 mL) / water (3.01 mL) The mixture was stirred at 100° C. for 4 hours. The mixture was cooled to room temperature. The mixture was cooled (UPLC showed approximately 50% conversion) and diluted with DCM and water. The crude product was purified by flash column chromatography. The mixture was purified by silica gel (SiO2, 0→100% ethyl acetate in hexane). , the title compound (658 mg, 2.77 mmol, 42% yield) and 86 There was obtained 6 mg (43%) of recovered starting material. 1 H NMR (400 MHz, CDCl 3)δ 8.01(s,1H),7.70-7.63(m,1H),7.11(s,1H ),3.90(s,3H),3.87(s,3H),2.25(s,3H),2.22( s,3H); 13 C NMR(101MHz,CDCl3)δ 167.27,165. 10,157.74,139.71,132.51,131.72,115.99,10 3.58,55.11,50.80,23.93,15.45;ESIMS m / z 2 36 [(MH) - ].

[0082] Example 3A: Preparation of 4-amino-2,5-dimethylbenzoic acid [ka] 4-Amino-2,5-dimethylphenyl in THF:MeOH:HO (3:2:1) (2 mL) A solution of methyl benzoate (0.11 g, 0.69 mmol) was added to LiOH (0.073 mg , 3.07 mmol) was added and the reaction mixture was stirred at 70° C. for 16 hours. The mixture was acidified with acetic acid (0.5 mL). The precipitated solid was filtered and dried to give a pale yellow solid. This gave the title compound (0.062 g, 68% yield). 1 H NMR (400MHz, CDCl3)δ 7.82(s,1H),6.48(s,1H),3.97(brs,2 H),2.54(s,3H),2.14(s,3H);ESIMS m / z 166([ M+H] + ).

[0083] Example 3B: Preparation of 4-amino-2-methoxy-5-methylbenzoic acid [ka] In a 50 mL round-bottom flask, 4-acetamido-2-methoxy-5-methylammonium Methyl benzoate (0.658 g, 2.77 mmol) was dissolved / suspended in 6M KOH aqueous solution. To the suspension was added MeOH (5 mL) at room temperature. The mixture was then heated to 60°C. The reaction was cooled to room temperature, diluted with water, and adjusted to pH approx. The mixture was carefully acidified to 4-5. The product was extracted with EtOAc (3x). The organic layer was dried over Na2SO4, filtered and concentrated to give the title compound ( Obtained 437 mg, 2.41 mmol, 87% yield. 1 H NMR (500MHz, C DCl3)δ 7.84(s,1H),6.25(s,1H),4.19(s,3H), 3.98(s,3H),2.11(s,3H); 13 C NMR (126MHz, CDC l3)δ 165.97,158.27,151.07,135.66,115.42, 106.65,96.62,56.49,16.15;ESIMS m / z 182[( M+H) + ].

[0084] Example 4: Preparation of 1-bromo-5-chloro-2-methyl-4-nitrobenzene [ka] 5-Chloro-2-methyl-4-nitroaniline (5.3 g, 28 mL) in acetic acid (53 mL) To a solution of 0.49 mmol) was added aqueous HBr (7.7 mL) at room temperature. 2 (1.96 g, 28.49 mmol) was added over 45 min. The reaction mixture was heated at 85 °C. The mixture was stirred for 2 hours. After 2 hours, the reaction mixture was cooled to room temperature and poured into ice water (100 mL). The resulting solid was filtered, washed with water (100 mL), dried and labeled as a pale yellow solid. The title compound was obtained (5.5 g, 74% yield). 1 H NMR (400MHz, CDCl3 )δ 7.79(s,1H),7.52(s,1H),2.45(s,3H).

[0085] Example 5: Preparation of 4-bromo-2-chloro-5-methylaniline [ka] Fe 0 Powder (12.1 g, 220.8 mmol) and NH4Cl (11.7 g, 220 1-Bromo-5-chloro- Add to a solution of 2-methyl-4-nitrobenzene (5.5 g, 22.08 mmol) at room temperature. The reaction mixture was stirred at 70° C. for 30 minutes. The reaction mixture was then cooled to room temperature and the solvent was removed. The crude material was diluted with water (30 mL), filtered, and the solid was dissolved in EtOAc ( The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers The extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography. Chromatography (silica gel (SiO2), 3→5% ethyl acetate in petroleum ether) ) to give the title compound (2.8 g, 58% yield) as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ 7.38(s,1H),6.65(s ,1H),3.96(brs,2H),2.27(s,1H);ESIMS m / z 2 20([M+H] + ).

[0086] Example 6A: Preparation of 4-amino-2,5-dichlorobenzonitrile [ka] 4-Bromo-2,5-dichloroaniline (2 g, 8.33 mm) in NMP (20 mL) To a solution of 1.2g of CuCN (2.2g, 24.99mmol), the reaction mixture was cooled to 37°C. The mixture was heated to 180° C. under microwave irradiation for 1.5 h. The reaction mixture was poured into ice-cold water (30 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. The crude product was purified by column chromatography (silica Gel (SiO2, 15→20% ethyl acetate in petroleum ether) to give a pale yellow The title compound was obtained as a solid (1 g, 64% yield). 1 H NMR (400MHz, C DCl3)δ 7.83(s,1H),6.92(s,1H),6.73(brs,2H );ESIMS m / z 187([M+H] + ).

[0087] Example 6B: Preparation of 4-amino-2,5-dimethylbenzonitrile [ka] 4-Bromo-2,5-dimethylaniline (15 g, 75.0 mL) in DMF (150 mL) A solution of Zn(CN)2 (9.6 g, 82.50 mmol) and Zn(CN)2 (9.6 g, 82.50 mmol) was degassed for 10 min. Next, tetrakis(triphenylphosphine)-palladium(0) (12.9 g , 11.25 mmol) was added and the reaction mixture was heated to 120° C. in a sealed tube for 2 days. After 2 days, the reaction mixture was poured into ice-cold water (400 mL) and The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel (SiO2), petroleum ether The product was purified by elution with 15% ethyl acetate in 100% methanol (15→20% ethyl acetate in 100% methanol) to give the title compound (5. 7 g, 52% yield was obtained. 1 H NMR (400MHz, CDCl3) δ 7.25( s,1H),6.50(s,1H),3.98(brs,2H),2.40(s,3H) ,2.11(s,3H);ESIMS m / z 147([M+H] + ).

[0088] Example 6C: Preparation of methyl 4-amino-5-methoxy-2-methylbenzoate [ka] 4-Bromo-2-methoxy-5-methylaniline (2.0 g, 9.3 mmol), acetic acid Palladium(II) (0.302 g, 1.345 mmol), 1,4-bis(diphenyl phosphanyl)butane (1.19 g, 2.79 mmol) and triethylamine (2.6 A solution of 1 mL of 19 mmol) was added to a 45 mL Parr reactor in MeOH (20 mL). The reactor was sealed and purged with CO (3 cycles from 50 to 100 psi). The reactor was then filled with CO to 400 psi, placed in a heat block, and heated to 130°C. The crude material was concentrated and the crude residue was dissolved in water (10 mL) and EtOAc ( The aqueous layer was dissolved in EtOAc (3×20 mL) and filtered through Celite. The combined organic layers were washed with brine (10 mL), dried over MgSO4, and filtered. The crude product was purified by column chromatography (silica gel (SiO2), petroleum ether The title compound was obtained as a rose-red solid by purification using a 0→40% ethyl acetate in ether mixture. The compound was obtained (363 mg, 20% yield). 1 H NMR (400MHz, CDCl3) δ 7.42(s,1H),6.50(s,1H),4.12(s,2H),3.87(s ,3H),3.84(s,3H),2.49(s,3H);ESIMS m / z 196 ([M+H] + ).

[0089] Example 7A: Preparation of 4-amino-2,5-dichlorobenzoic acid [ka] 4-Amino-2,5-dichlorobenzonitrile (1 g, 5.37 m To a solution of 1.0 g (107.52 mmol), KOH (6.0 g, 107.52 mmol) was added at room temperature, and the reaction mixture The mixture was heated to 120 °C in a sealed tube for 2 days. After 2 days, the reaction mixture was diluted with EtO The aqueous layer was acidified with acetic acid (12 mL) and diluted with 10 The combined organic layers were dried over anhydrous Na2SO4 and extracted with MeOH (2 x 75 mL). , filtered and concentrated under reduced pressure to give the title compound (0.7 g, 63% yield) as a pale yellow solid. which was used in the next step without further purification. 1 H NMR(40 0MHz, CDCl3)δ 7.61(s,1H),6.77(s,1H),5.89( brs,2H);ESIMS m / z 206([M+H] + ).

[0090] Example 7B: Preparation of 4-amino-5-methoxy-2-methylbenzoic acid [ka] Methyl 4-amino-5-methoxy-2-methylbenzoate (155 mg, 0.794 mm A solution of (86 mg, 3.6 mmol) and lithium hydroxide (86 mg, 3.6 mmol) in 3:2:1 THF: Prepared in MeOH:water (2.4 mL). Stir the resulting dark purple reaction at 70° C. overnight. The reaction was then acidified to approximately pH=4 by careful addition of 1M HCl, and a solid was precipitated. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with anhydrous MgS Dry over O4, filter, and concentrate under reduced pressure to give the title compound (92 mg) as a dark green solid. , 64%), which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ 11.95(s,1H),7.29(s ,1H),6.44(s,1H),5.40(s,2H),3.75(s,3H),2. 37(s,3H); 13 C NMR(126MHz,DMSO-d6)δ 168.71 ,143.69,142.34,134.93,116.12,115.89,113. 25,55.76,21.98;IR (thin film)3500,3396,2935,2836 ,1669,1608,1529,1451,1364,1258,1217,1081 ,1022,867cm -1 ;HRMS-ESI(m / z)[M+H]+ C9H 12 N Calculated value for O3: 182.0812; measured value: 182.0812.

[0091] Example 8A: Preparation of 1-(p-tolyl)propan-1-ol [ka] In a 250 mL flask, a solution of 4-methylbenzaldehyde (0.736 m L, 6.24 mmol) in diethyl ether (31.2 mL) and placed in an ice bath. The clear solution was cooled to 0° C. with ethylmagnesium bromide (1M in THF, 7.49 mL, 7.49 mmol) was added dropwise over 5 min and the resulting solution was stirred overnight. The mixture was stirred and allowed to warm slowly to room temperature so that the ice bath melted. After 18 hours, TLC showed that the starting material The reaction was cooled to room temperature and the conversion of the product to more polar products was observed. The mixture was quenched with 100 mL of ethyl acetate and extracted with diethyl ether (3×50 mL). The mixture was passed through a phase separator and concentrated to a clear oil. The crude material was subjected to flash column chromatography. The mixture was purified by silica gel (SiO2, 0→50% ethyl acetate in hexane). to give the title compound (476 mg, 1.89 mmol, 51% yield) as a clear, colorless oil. Got it. 1 H NMR(500MHz,CDCl3)δ 7.24-7.20(m,2H) ,7.15(d,J=7.9Hz,2H),4.54(ddd,J=7.0,4.7,1 .6Hz,1H),2.34(s,3H),1.88-1.68(m,3H),0.90 (t, J = 7.4 Hz, 3 H); 13 C NMR (126MHz, CDCl3) δ 14 1.64, 137.15, 129.08, 125.93, 75.89, 31.80, 21 .11,10.20;IR(thin film)3340,2962,2926,1454,1097 ,1039,1012,815cm -1 .

[0092] Example 8B: Preparation of (R)-1-(p-tolyl)ethan-1-ol [ka] In a 100 mL flask, 1-(p-tolyl)ethan-1-one (0.747 mL, 5.59 mmol) and (S)-1-methyl-3,3-diphenyltetrahydro- 1H,3H-Pyrrolo[1,2-c][1,3,2]oxaborole ((S)-CBS catalyst) , 1M in toluene, 1.118 mL, 1.118 mmol) in toluene (37. 3 mL) and cooled to 0° C. in an ice / water bath. Then, BH3-DMS (T HF (2M, 3.49 mL, 6.99 mmol) was added via syringe over 2 min. The ice bath was removed. The reaction was stirred at room temperature. After 1 h, TLC showed no consumption of starting material. Methanol (2.27 mL, 55.9 mmol) was slowly added and the reaction Concentration gave a clear, colorless oil. The crude material was purified by flash column chromatography (silica gel). Purification by silica gel (SiO2, 0→50% ethyl acetate in hexane) gave a clear, colorless The title compound was obtained as an oil (784 mg, 5.76 mmol, quantitative yield). 1 HN MR(500MHz,CDCl3)δ 7.26(d,J=8.0Hz,2H),7.1 6(d,J=7.9Hz,2H),4.86(qd,J=6.4,2.7Hz,1H), 2.34(s,3H),1.78(d,J=3.1Hz,1H),1.48(d,J=6 .5Hz,3H); 13 C NMR(126MHz,CDCl3)δ 142.88,1 37.16,129.17,125.35,70.26,25.08,21.09;IR (Thin film)3341,2971,1513,1071,1009,897,816cm -1 .

[0093] Example 9A: Preparation of 4-methylbenzyl 4-amino-2,5-dimethylbenzoate [ka] In a 20 mL vial, p-tolylmethanol (222 mg, 1.82 mmol) was added. l), 4-amino-2,5-dimethylbenzoic acid (150 mg, 0.908 mmol) and DMAP (11.1 mg, 0.091 mmol) was dissolved in DCM (4.45 mL). The mixture was cooled to 0° C. in an ice / water bath. After about 5 minutes, EDC (211 mg, 1.36 mmol) was added in one portion and the resulting pale yellow reaction was stirred overnight and then allowed to warm slowly to room temperature to allow the ice to melt. After 18 h, TLC indicated consumption of starting material. The reaction was concentrated to give an oil. The crude material was purified by flash column chromatography (C18 reverse phase, 50 → 100 in water). % acetonitrile) to give the title compound (192 mg, 0.712 mmol, 78% yield was obtained. 1 H NMR (400MHz, CDCl3) δ 7.74(s,1H),7.36-7.29(m,2H),7.18(d,J=7. 8Hz,2H),6.46(s,1H),5.25(s,2H),3.88(s,2H) ,2.52(s,3H),2.36(s,3H),2.12(s,3H); 13 CNM R(101MHz,CDCl3)δ 167.17,148.26,140.79,13 7.70,133.84,133.80,129.17,128.24,118.63, 117.06,77.22,65.78,21.98,21.20,16.59;HRM S-ESI(m / z)[M+H] + C 17 H 20 Calculated value for NO2: 270.14 89;Actual value: 270.1477.

[0094] Example 9B: Preparation of 2-methylbenzyl 4-amino-2,5-dimethylbenzoate [ka] 4-Amino-2,5-dimethylbenzoic acid (4.2 g, 25.4 mL) in DMF (40 mL) 5 mmol) of 1-(bromomethyl)-2-methylbenzene (3.5 mL , 25.45 mmol) and K2CO3 (3.8 g, 27.99 mmol) were added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then poured into ice-cold water (100 mL) and Extraction with tOAc (2×200 mL) was performed. The combined organic layers were dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography (silica Gel (SiO2, 10→15% ethyl acetate in hexane) to give an off-white solid The title compound (3.8 g, yield 55%) was obtained as above. 1 H NMR (400MHz, C DCl3)δ 7.74(s,1H),7.40(d,1H),7.20(m,3H), 6.47(s,1H),5.29(s,2H),3.89(brs,2H),2.52( s,3H),2.40(s,3H),2.11(s,3H);ESIMS m / z 27 0([M+H] + ).

[0095] Example 9C: Preparation of 1-(p-tolyl)propyl 4-amino-2,5-dimethylbenzoate [ka] Contains 4-amino-2,5-dimethylbenzoic acid (200 mg, 1.21 mmol) Add 2-(p-tolyl)propan-2-ol (364 mg, 2.42 mL) to a 20 mL vial. DCM (12. 1 mL) was added, followed by N-ethyl-N-isopropylpropan-2-amine (844 μl (4.84 mmol) was added dropwise over 45 seconds. After 10 minutes, most of the solid was soluble. The resulting pale pink reaction was allowed to stir at room temperature overnight. After 18 hours, the reaction was filtered. The crude material was purified by flash column chromatography (C 18Reverse phase, 50→100% acetonitrile in water) to give the title compound as an orange oil. The compound was obtained (107 mg, 0.36 mmol, 30% yield). 1 H NMR (500M Hz,CDCl3)δ 7.77(s,1H),7.33 7.27(m,2H),7. 18 7.10(m,2H),6.44(s,1H),5.82(t,J=6.8Hz, 1H),3.87(s,2H),2.51(s,3H),2.32(s,3H),2.1 4(s,3H),2.03(dt,J=13.7,7.5Hz,1H),1.90(tt ,J=13.7,7.4Hz,1H),0.94(t,J=7.4Hz,3H); 13 C NMR(126MHz,CDCl3)δ 166.70,148.20,140.65 ,138.30,137.17,133.76,129.02,126.50,118. 97,118.60,117.06,76.92,29.66,22.08,21.14 ,16.70,10.17;IR(thin film)3376,2967,2927,1689,1 624,1562,1253,1156,1053,814cm -1; HRMS-ESI (m / z) [M+H] + C 19 H 24 Calculated value for NO2: 298.1802; measured value Value,298.1801.

[0096] Example 10A: (E)-4-(((ethyl(methyl)amino)methylene)amino)-2, Preparation of 4-methylbenzyl 5-dimethylbenzoate [ka] In a 100 mL round bottom flask, 4-methyl-4-amino-2,5-dimethylbenzoate A solution of ethylbenzyl (359 mg, 1.33 mmol) in toluene (26.6 mL) Next, N-(dimethoxymethyl)-N-methylethanamine (532 mg, 4 0.00 mmol) was added, and the resulting solution was fitted with a reflux condenser, heated to 80° C., and 4 The mixture was stirred for 8 h. After 48 h, the solution was concentrated to an oil. The crude material was purified by flash column chromatography. Purified by column chromatography (C18 reverse phase, 30 → 100% acetonitrile in water) This gave the title compound (333 mg, 0.98 mmol, 74% yield) as a brown oil. .1 H NMR(400MHz,CDCl3)δ 7.79(s,1H),7.45(s ,1H),7.33(d,J=7.9Hz,2H),7.17(d,J=7.8Hz,2 H),6.56(s,1H),5.26(s,2H),3.39(bd,J=67.1H z,2H),2.99(s,3H),2.55(s,3H),2.35(s,3H),2 .22(s,3H),1.20(t,J=7.1Hz,3H); 13 C NMR(101 MHz,CDCl3)δ 167.49,154.64,151.69,139.49, 137.70, 133.73, 132.81, 129.17, 128.79, 128.2 7,122.55,121.90,65.92,47.85,32.02,21.80, 21.18,17.41,14.37;ESIMS m / z 339[(M+H) + ].

[0097] Example 10B: (E)-4-(((diethylamino)methylene)amino)-2,5-dimethylamino Preparation of 4-methylbenzyl methylbenzoate [ka] In a 20 mL vial, 4-methyl-4-amino-2,5-dimethylbenzoate was added. 100 mg (0.37 mmol) in triethyl orthoformate (2 mL, 12.0 mmol) followed by p-toluenesulfonic acid monohydrate (7.06 mg, 0. 03 mmol) was added. The reaction was heated to reflux (140° C.) and stirred for 3 h. After a period of time, TLC showed nearly complete conversion of the starting material. The reaction was diluted with saturated aqueous NaHCO (10 mL) and extracted with DCM (3×10 mL). The residue was redissolved in DCM (0.371 mL). Diethylamine (0.058 mL, 0.55 mmol) was then added dropwise via syringe. The solution was heated to 40° C. and stirred for 3 h. The reaction was quenched with water (10 mL). The combined organic phase was passed through a phase separator and concentrated. The crude material was purified by flash column chromatography (C18 reverse phase, 30 → 100 in water). % acetonitrile) to give the title compound (75.8 mg, 0.2 1 mmol, 58% yield was obtained. 1 H NMR (500 MHz, CDCl3) δ 7. 79(t,J=1.4Hz,1H),7.42(s,1H),7.38 7.30(m, 2H),7.18(dt,J=6.6,1.7Hz,2H),6.55(s,1H),5 .26(s,2H),3.40(d,J=94.6Hz,4H),2.55(s,3H) ,2.36(s,3H),2.22(s,3H),1.22(t,J=7.1Hz,6H );IR(thin film)2970,2927,1707,1629,1592,1549,13 71,1250,1110,1047cm -1 ;HRMS-ESI(m / z)[M+H] + C 22 H 29 Calculated value for N2O2: 353.2224; measured value: 353.222 7.

[0098] Example 10C: (E)-2,5-Dimethyl-4-(piperidin-2-ylideneamino)ammonium Preparation of 4-methylbenzyl benzyl ester [ka] In a 20 mL vial, piperidin-2-one (0.103 mL, 1.11 m A solution of 100 mol) was prepared in toluene (9 mL) under N2. Then, phosphoryl trichloride ( 0.052 mL, 0.55 mmol) was added and the cloudy reaction was stirred at room temperature for 2 h. 4-Methylbenzyl-4-amino-2,5-dimethylbenzoate (150 mg, 0 0.55 mmol) and attach the reaction to a reflux condenser and heat at reflux (110 °C) for 3 h. The resulting transparent gold reaction mixture was then cooled to room temperature and purified with 10% NaOH aqueous solution. The crude reaction was stirred overnight. The layers were separated. The aqueous layer was separated and washed with ethyl acetate (3×20 mL). The combined organic layers were washed with brine. , dried over Na2SO4, filtered and concentrated to an oil. SCX column (DCM, The crude material was purified using toluene (equilibrated with MeOH). The material was dissolved in DCM and The column was loaded with DCM and MeOH to elute the undesired components. The SCX column was run with 7N NH3 in H to give the title compound (95.0 mg) as a yellow oil. , 0.27 mmol, 49% yield. 1 H NMR (600MHz, CDCl3) δ 7.79(s,1H),7.34(d,J=7.8Hz,2H),7.19(d,J =7.8Hz,2H),6.63(s,1H),5.27(s,2H),4.39(s, 1H),3.22(d,J=100.6Hz,2H),2.59(d,J=31.6Hz ,2H),2.52(s,3H),2.36(s,3H),2.07(s,3H),1. 76(dh,J=8.3,4.0,3.3Hz,4H); 13 C NMR (151MHz ,CDCl3)δ 167.43,155.09,152.08,139.70,137 .84,133.52,133.42,129.21,128.35,127.29,1 25.05,123.33,66.08,42.55,30.85,23.06,21. 70,21.22,21.14,17.02;ESIMS m / z 351[(M+H) + ].

[0099] Example 10D: 4-(3,3-diethylthioureido)-2,5-dimethylbenzoic acid 4- Preparation of methylbenzyl [ka] In a 20 mL vial, 4-methyl-4-amino-2,5-dimethylbenzoate was added. (100 mg, 0.37 mmol) and sodium bicarbonate (312 mg, 3.7 A solution of 1 mmol) was prepared in DCM (1.24 mL) and water (1.24 mL). Thiophosgene (31.3 μL, 0.40 mmol) was added dropwise via syringe to the solution. The resulting orange biphasic mixture was stirred vigorously at room temperature for 2 hours. After 2 hours, TLC showed The biphasic mixture was diluted with water (5 mL) and DCM (5 mL). The crude material was diluted with DCM (1.24 mL) and concentrated to give a pale yellow oil. The solution was then redissolved in 50 mL of 100 mL of 100% ethanol, followed by diethylamine (77 μL, 0.74 mmol) via syringe. The resulting solution was stirred at room temperature for 1 hour. After 1 hour, the solution became an oil. The crude material was purified by flash column chromatography (silica gel (SiO ), 0→50% ethyl acetate in hexanes) to give the title compound as a white semi-solid. The compound (140.0 mg, 0.36 mmol, yield 98%) was obtained. 1 H NMR(400 MHz, CDCl3)δ 7.81(s,1H),7.36-7.28(m,2H),7 .23-7.15(m,3H),6.75(s,1H),5.27(s,2H),3.7 6(q,J=7.1Hz,4H),2.54(s,3H),2.36(s,3H),2. 23(s,3H),1.31(t,J=7.1Hz,6H); 13 C NMR (101M Hz,CDCl3)δ 180.90,167.00,141.68,138.92,1 38.00,133.26,133.19,130.80,129.63,129.26 ,128.37,127.11,66.42,45.82,21.54,21.21,1 7.59,12.70;IR (thin film)3240,2974,1713,1516,125 8,1141,1055,806,728cm -1 ;HRMS-ESI(m / z)[M+ H] + C 22 H 29 Calculated value for N2O2S: 385.1944; measured value: 385. 1950.

[0100] Example 10E: (Z)-4-((methoxy(methylamino)methylene)amino)-2,5 Preparation of 2-methylbenzyl dimethylbenzoate [ka] 2-Methyl 4-amino-2,5-dimethylbenzoate in trimethyl orthoformate (6 mL) A solution of ruthenium benzil (0.22 g, 0.81 mmol) was refluxed at 120° C. for 16 h. The reaction mixture was then concentrated under reduced pressure to give 0.22 g of crude product as a pale yellow gummy liquid. 4-((methoxymethylene)amino)-2,5-dimethylbenzoate 2-methylbenzyl The crude material was then dissolved in 1,4-dioxane (3 mL) and methanol (3 mL). To this solution was added N,O-dimethylhydroxylamine hydrochloride (0.97 g, 0.7 1 mmol) and triethylamine (0.09 mL, 0.71 mmol) were then added. The reaction mixture was stirred in a sealed tube at 80° C. for 16 hours. The reaction mixture was cooled to room temperature under reduced pressure. The crude material was purified by preparative HPLC and shown as an off-white solid. The title compound was obtained (12 mg, 4% yield). mp 90-92°C; 1 H NMR(400 MHz,DMSO-d6)δ 7.67(s,1H),7.38(d,J=6.8Hz, 1H),7.27-7.20(m,3H),6.62(s,1H),5.59-5.51 (m,1H),5.28(s,2H),3.73(s,3H),2.54(d,J=4. 8Hz,3H),2.43(s,3H),2.35(s,3H),2.01(s,3H) ;ESIMS m / z 341([M+H] + ).

[0101] Example 11: (E)-4-(((ethyl(methyl)amino)methylene)amino)-2,5 Preparation of -dimethylbenzoic acid [ka] In a 25 mL vial, (E)-4-(((ethyl(methyl)amino)methyl) Solution of 2,5-dimethylbenzoate (1.20 g, 4.83 mmol) was prepared in methanol (9.66 mL). Then, an aqueous solution of NaOH (1 M, 4.83 mL) was added. L, 4.83 mmol) was added and the reaction was heated to 60° C. and stirred overnight. The reaction was then cooled to room temperature and concentrated to dryness. The reaction was redissolved in water (20 mL) and The aqueous layer was acidified with dilute 1N HCl and diluted with DCM (3×20 No material was observed in the organic layer, so the aqueous layer was concentrated to give the crude material. The mixture was purified by flash column chromatography (C18 reversed phase, 10 → 90% acetonitrile in water). Purification by HPLC (HPLC) afforded the title compound (443 mg, 1.89 mmol, 1 hexanediaminetetraacetate) as a tan solid. The yield was 39%). 1 H NMR(400MHz,DMSO-d6)δ 12.94( s,1H),11.20(s,1H),8.40(d,J=56.6Hz,1H),7. 76(s,1H),7.31(d,J=10.6Hz,1H),3.70(dq,J=4 6.9,7.1Hz,2H),3.30(d,J=2.6Hz,3H),2.50(dd ,J=3.7,1.9Hz,2H),2.36(d,J=2.5Hz,3H),1.26 (dt,J=9.7,7.1Hz,3H);mp>250℃;ESIMS m / z 33 5 [(M+H) + ].

[0102] Example 12: (Z)-4-(((ethyl(methyl)amino)(methylthio)methylene)a Preparation of 3-(trifluoromethyl)benzyl(amino)-2,5-dimethylbenzoate [ka] 4-(3-ethyl-3-methylthioureido)-2,5-dimethylbenzoic acid 3-(trimethylbenzoate A solution of (0.050 g, 0.118 mmol) benzyl fluoromethyl in acetone (1 The solution was added with K2CO3 (0.033 g, 0.24 mmol). and iodomethane (10 μL, 0.16 mmol) were added. The mixture was then cooled to ambient temperature. The reaction was then diluted with ethyl acetate (50 mL) and passed through Celite. The crude material was purified by flash column chromatography (silica gel). The compound was purified by silica gel (SiO2, 0→70% ethyl acetate in hexane) to give a clear oil. This gave the title compound (49 mg, 0.11 mmol, 95% yield). 1 H NMR( 500MHz, CDCl3)δ 7.82-7.78(m,1H),7.71(d,J= 1.8Hz,1H),7.64(d,J=7.6Hz,1H),7.59(d,J=7. 8Hz,1H),7.51(t,J=7.7Hz,1H),6.68(s,1H),5. 35(s,2H),3.57(q,J=7.1Hz,2H),3.08(s,3H),2 .54(s,3H),2.14(s,3H),1.94(s,3H),1.20(t,J =7.0Hz,3H); 19 F NMR (471MHz, CDCl3) δ -62.60 ;ESIMS m / z 439[(M+H) + ].

[0103] Example 13: 4-(((ethyl(methyl)amino)methylene)amino)-2,3-dimethyl Preparation of 3-(trifluoromethyl)benzyl benzoate hydrochloride [ka] (E)-4-(((ethyl(methyl)amino)methylene)amino)-2,3-dimethyl 3-(Trifluoromethyl)benzyl benzoate was dissolved in heptane and transferred to a separatory funnel. 2N HCl was added and the resulting layers were separated. The heptane layer was discarded and the aqueous layer was diluted with ethyl acetate. The organic layer was concentrated to give 4 as a light brown solid and a ca. 2:1 mixture of E:Z isomers. -(((ethyl(methyl)amino)methylene)amino)-2,3-dimethylbenzoic acid 3- (Trifluoromethyl)benzyl hydrochloride (237 mg, 0.553 mmol) was obtained. 1 H NMR(500MHz,CDCl3)δ 12.64-12.53(m,1H),7 .95-7.86(m,1H),7.70-7.65(m,1H),7.65-7.57 (m,3H),7.56-7.49(m,1H),7.28-7.22(m,0.6H) ,5.37(s,2H),4.00(q,J=7.2Hz,0.6H),3.64(q, J=7.2Hz,1.4H),3.50(s,2H),3.33(s,1H),2.44 (s,3H),2.38(s,3H),1.36-1.28(m,3H); 19 F.N.M. R(471MHz,CDCl3)δ -62.64;HRMS-ESI(m / z)[M+ H] + C 21 H 23 Calculated value for F3N2O2: 393.1784, measured value: 393 .1793;mp172-176℃.

[0104] Overall biological experiment details Example A: Evaluation of fungicidal activity: against wheat leaf spot (Zymoceptoria tritici) eptoria tritici); Bayer code SEPTTR): The technical grade material was dissolved in acetone, which was then diluted with 110 ppm Triton The fungicide solution was mixed with 9 volumes of water (H2O) containing X-100. The product was applied to wheat seedlings using a sprayer until runoff. All treated plants were then removed for further treatment. All fungicides were sterilized using the methods previously described unless otherwise stated. were evaluated for their activity against the target diseases.

[0105] Wheat plants (variety "Yuma") were grown in a greenhouse from seeds in soilless potting medium. Seven to 10 seedlings were grown per pot until one leaf fully emerged. These plants The treatments were performed 3 days before (3-day treatment; 3DC) or 1 day after (1-day treatment; 1DC) fungicide treatment. Zymoseptor tritici (Zymoseptor 1DP) After inoculation, the plants were inoculated with an aqueous spore suspension of B. japonica tritici. The plants were then kept at room temperature for 3 days to allow the spores to germinate and infect the leaves. The disease symptoms were fully manifested on the first leaves of untreated plants. The infection level was assessed on a scale of 0 to 100 percent disease severity. The percentage was calculated using the ratio of disease severity between treated and untreated plants.

[0106] Example B: Evaluation of fungicidal activity: Wheat leaf rust (Puccinia triticinae) Synonym: Puccinia recondita differentiated triticina (Pucci nia recondita f.sp.tritici);Bayer code PUCC RT): Wheat plants (variety "Yuma") were grown in a greenhouse from seeds in soilless potting medium. Seven to 10 seedlings were grown per pot until one leaf fully emerged. These plants After fungicide treatment, Puccinia triticina After inoculation, the plants were kept in a dark fog room at 100% relative humidity. The plants were then kept overnight to allow the spores to germinate and infect the leaves. The plants were then placed in a warm place to allow the disease to develop. The fungicide formulations, applications and disease evaluations followed the procedures described in Example A.

[0107] Example C: Evaluation of fungicidal activity: Asian soybean rust (Phakopsora pachyrhizi) opsora pachyrhizi);Bayer code PHAKPA): Technical grade material was dissolved in acetone, which was then diluted with 0.011% Tween 2. The fungicide solution was mixed with 9 volumes of H2O containing 0.01% water. All sprayed plants were allowed to air dry before further handling. I did.

[0108] Soybean plants (variety "Williams 82") were grown in soilless potting medium in one pot. The plants were grown at one plant per day. 10-day-old seedlings were used for the tests. The plants were The plants were inoculated as described. The plants were incubated in a dark fog chamber with 100% relative humidity for 24 h. The plants were then baited and subsequently transferred to a growth room to allow disease to develop. The results were as described in Example A. When the disease symptoms were fully manifested, the disease severity was calculated as: The percentage of disease control was evaluated on a scale of 0 to 100 percent for treated leaves. The disease severity was calculated using the ratio of disease severity between treated and untreated plants.

[0109] Example D: Evaluation of fungicidal activity: Barley leaf spot (Rhynchosporium secharis) nchosporium secalis); Bayer code RHYNSE): Barley plants (variety "Harrington") were grown in soilless potting medium in a greenhouse. Seven to 10 seedlings were grown per pot until the first leaves fully emerged from the seeds in the pot. These plants showed increased phytoplankton production after fungicide treatment. The plants were inoculated with an aqueous spore suspension of P. secalis. After inoculation, the plants were The plants were then kept in a dark mist chamber at 0% relative humidity for 2 days to allow the spores to germinate and infect the leaves. The plants were then transferred to a greenhouse to allow disease to develop. The fungicide formulations and applications were as described in Example A. Disease assessment was performed as described in Example A.

[0110] Example E: Evaluation of fungicidal activity: Barley spot disease (Cochriobolus sativus) liobolus sativus);Bayer code COCHSA): Barley seedlings (variety Harrington) were grown in pots containing 8–12 plants each. The plants were propagated in soilless potting medium by 100°C and used for testing when the first leaves had fully emerged. Test plants were infested with Cochliobolus sativus (Cochli) 24 hours after fungicide treatment. The plants were inoculated with a spore suspension of B. obolus sativus. After inoculation, 100% of the plants were The plants were then kept at 4°C for 2 days at a relative humidity of 10% to allow the spores to germinate and infect the leaves. The plants were then transferred to a greenhouse to allow disease to develop. Fungicide formulations, applications and disease evaluations were as described in Example A. The procedure described was followed.

[0111] [Table 1C-1]

[0112] [Table 1C-1]

[0113]

Table 1C-2

[0114]

Table 1C-3

[0115]

Table 1C-4

[0116]

Table 1C-5

[0117]

Table 1C-6

[0118]

Table 1C-7

[0119]

Table 1C-8

[0120]

Table 1C-9

[0121]

Table 1C-10

[0122]

Table 1C-11

[0123]

Table 1C-12

[0124]

Table 1C-13

[0125]

Table 1C-14

[0126]

Table 1C-15

[0127]

Table 1C-16

[0128]

Table 1C-17

[0129]

Table 1C-18

[0130]

Table 1C-19

[0131]

Table 1C-20

[0132]

Table 1C-21

[0133]

Table 1C-22

[0134]

Table 1C-23

[0135]

Table 1C-24

[0136]

Table 1C-25

[0137]

Table 1C-26

[0138]

Table 1C-27

[0139]

Table 1C-28

[0140]

Table 1C-29

[0141]

Table 1C-30

[0142]

Table 1C-31

[0143]

Table 1C-32

[0144]

Table 1C-33

[0145]

Table 1C-34

[0146]

Table 1C-35

[0147]

Table 1C-36

[0148]

Table 1C-37

[0149]

Table 1C-38

[0150]

Table 1C-39

[0151]

Table 1C-40

[0152]

Table 1C-41

[0153]

Table 1C-42

[0154]

Table 1C-43

[0155]

Table 1C-44

[0156]

Table 1C-45

[0157]

Table 1C-46

[0158]

Table 1C-47

[0159]

Table 1C-48

[0160]

Table 1C-49

[0161]

Table 1C-50

[0162]

Table 1C-51

[0163]

Table 1C-52

[0164]

Table 1C-53

[0165]

Table 1C-54

[0166]

Table 1C-55

[0167]

Table 1C-56

[0168]

Table 1C-57

[0169]

Table 1C-58

[0170]

Table 1C-59

[0171]

Table 1C-60

[0172]

Table 1C-61

[0173]

Table 1C-62

[0174]

Table 1C-63

[0175]

Table 1C-64

[0176]

Table 1C-65

[0177]

Table 1C-66

[0178]

Table 1C-67

[0179]

Table 1C-68

[0180]

Table 1C-69

[0181]

Table 1C-70

[0182]

Table 1C-71

[0183]

Table 1C-72

[0184]

Table 1C-73

[0185]

Table 1C-74

[0186]

Table 1C-75

[0187]

Table 1C-76

[0188]

Table 1C-77

[0189]

Table 1C-78

[0190]

Table 1C-79

[0191]

Table 1C-80

[0192]

Table 1C-81

[0193]

Table 1C-82

[0194]

Table 1C-83

[0195]

Table 1C-84

[0196]

Table 1C-85

[0197]

Table 1C-86

[0198]

Table 1C-87

[0199]

Table 1C-88

[0200]

Table 1C-89

[0201]

Table 1C-90

[0202]

Table 1C-91

[0203]

Table 1C-92

[0204]

Table 1C-93

[0205]

Table 1C-94

[0206]

Table 1C-95

[0207]

Table 1C-96

[0208]

Table 1C-97

[0209]

Table 2-1

[0210]

Table 2-2

[0211]

Table 2-3

[0212]

Table 2-4

[0213]

Table 2-5

[0214]

Table 2-6

[0215]

Table 2-7

[0216]

Table 2-8

[0217]

Table 2-9

[0218]

Table 2-10

[0219]

Table 2-11

[0220]

Table 2-12

[0221]

Table 2-13

[0222]

Table 2-14

[0223]

Table 2-15

[0224]

Table 2-16

[0225]

Table 2-17

[0226]

Table 2-18

[0227]

Table 2-19

[0228]

Table 2-20

[0229]

Table 2-21

[0230]

Table 2-22

[0231]

Table 2-23

[0232]

Table 2-24

[0233]

Table 2-25

[0234]

Table 2-26

[0235]

Table 2-27

[0236]

Table 2-28

[0237]

Table 2-29

[0238]

Table 2-30

[0239]

Table 2-31

[0240]

Table 2-32

[0241]

Table 2-33

[0242]

Table 2-34

[0243]

Table 2-35

[0244]

Table 2-36

[0245]

Table 2-37

[0246]

Table 2-38

[0247]

Table 2-39

[0248]

Table 2-40

[0249]

Table 2-41

[0250]

Table 2-42

[0251]

Table 2-43

[0252]

Table 2-44

[0253]

Table 2-45

[0254]

Table 2-46

[0255]

Table 2-47

[0256]

Table 2-48

[0257]

Table 2-49

[0258]

Table 2-50

[0259]

Table 2-51

[0260]

Table 2-52

[0261]

Table 2-53

[0262]

Table 2-54

[0263]

Table 2-55

[0264]

Table 2-56

[0265]

Table 2-57

[0266]

Table 2-58

[0267]

Table 2-59

[0268]

Table 2-60

[0269]

Table 2-61

[0270]

Table 2-62

[0271]

Table 2-63

[0272]

Table 2-64

[0273]

Table 2-65

[0274]

Table 2-66

[0275]

Table 2-67

[0276]

Table 2-68

[0277]

Table 2-69

[0278]

Table 2-70

[0279]

Table 2-71

[0280]

Table 2-72

[0281]

Table 2-73

[0282]

Table 2-74

[0283]

Table 2-75

[0284]

Table 2-76

[0285]

Table 2-77

[0286]

Table 2-78

[0287]

Table 2-79

[0288]

Table 2-80

[0289]

Table 2-81

[0290]

Table 2-82

[0291]

Table 2-83

[0292]

Table 2-84

[0293]

Table 2-85

[0294]

Table 2-86

[0295]

Table 2-87

[0296]

Table 2-88

[0297]

Table 2-89

[0298]

Table 2-90

[0299]

Table 2-91

[0300]

Table 2-92

[0301]

Table 2-93

[0302]

Table 2-94

[0303]

Table 2-95

[0304]

Table 2-96

[0305]

Table 2-97

[0306]

Table 2-98

[0307]

Table 2-99

[0308]

Table 2-100

[0309]

Table 2-101

[0310]

Table 2-102

[0311]

Table 2-103

[0312]

Table 2-104

[0313]

Table 2-105

[0314]

Table 2-106

[0315]

Table 2-107

[0316]

Table 2-108

[0317]

Table 2-109

[0318]

Table 2-110

[0319]

Table 2-111

[0320]

Table 2-112

[0321]

Table 2-113

[0322]

Table 2-114

[0323]

Table 2-115

[0324]

Table 2-116

[0325]

Table 2-117

[0326]

Table 2-118

[0327]

Table 2-119

[0328]

Table 2-120

[0329]

Table 2-121

[0330]

Table 2-122

[0331]

Table 2-123

[0332]

Table 2-124

[0333]

Table 2-125

[0334]

Table 2-126

[0335]

Table 2-127

[0336]

Table 2-128

[0337]

Table 2-129

[0338]

Table 2-130

[0339]

Table 2-131

[0340]

Table 2-132

[0341]

Table 2-133

[0342]

Table 2-134

[0343]

Table 2-135

[0344]

Table 2-136

[0345]

Table 2-137

[0346]

Table 2-138

[0347]

Table 2-139

[0348]

Table 2-140

[0349]

Table 2-141

[0350]

Table 2-142

[0351]

Table 2-143

[0352]

Table 2-144

[0353]

Table 2-145

[0354]

Table 2-146

[0355]

Table 2-147

[0356]

Table 2-148

[0357]

Table 2-149

[0358]

Table 2-150

[0359]

Table 2-151

[0360]

Table 2-152

[0361]

Table 2-153

[0362]

Table 2-154

[0363]

Table 2-155

[0364]

Table 2-156

[0365]

Table 2-157

[0366]

Table 2-158

[0367]

Table 2-159

[0368]

Table 2-160

[0369]

Table 2-161

[0370]

Table 2-162

[0371]

Table 2-163

[0372]

Table 2-164

[0373]

Table 2-165

[0374]

Table 2-166

[0375]

Table 2-167

[0376]

Table 2-168

[0377]

Table 2-169

[0378]

Table 2-170

[0379]

Table 2-171

[0380]

Table 2-172

[0381]

Table 3

[0382]

Table 4-1

[0383]

Table 4-2

[0384]

Table 4-3

[0385]

Table 4-4

[0386]

Table 4-5

[0387]

Table 4-6

[0388]

Table 4-7

[0389]

Table 4-8

[0390]

Table 4-9

[0391]

Table 4-10

[0392]

Table 4-11

[0393]

Table 4-12

[0394]

Table 4-13

[0395]

Table 4-14

[0396]

Table 4-15

[0397]

Table 4-16

[0398]

Table 4-17

Claims

1. Formula I: 【Chemistry 1】 (In the formula, R １ is hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, C ２ ~C ８ Alkenyl, C ２ ~C ８ Substituted alkenyl, C ２ ~C ８ Alkynyl, C ２ ~C ８ Substituted alkynyl, C ３ ~ C ８ Cycloalkyl, C ３ ~C ８ Substituted cycloalkyl, C ３ ~C ８ Heterocycloalkyl , C ３ ~C ８ Substituted Heterocycloalkyl, C ５ ~C ７ Heteroaryl, C ５ ~C ７ Substitution Selected from the group consisting of aryl, phenyl, substituted phenyl, benzyl and substituted benzyl And; Each R ２ , R ３ , R ４ and R ５ are independently hydrogen, halogen, cyano, nitro, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, C ２ ~C ８ Alkenyl, C ２ ~C ８ Substituted alkenyl Lu, C ２ ~C ８ Alkynyl, C ２ ~C ８ Substituted alkynyl, C １ ~C ８ Alkoxy and C １ ~C ８ substituted alkoxy; R ６ is hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, C ２ ~C ８ Alkenyl, C ２ ~C ８ Substituted alkenyl, C ２ ~C ８ Alkynyl, C １ ~C ８ Substituted alkynyl, C １ ~ C ８ Alkoxy, C １ ~C ８ Substituted alkoxy, thiol, alkylthio and substituted alkyl or is selected from the group consisting of thio; R ６ and R ７ are covalently bonded together and are saturated or unsaturated C ３ ~C ８ Heterocycloar Kill or C ３ ~C ８ It may form a substituted heterocycloalkyl group; Each R ７ and R ８ are independently hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, C ２ ~C ８ Alkenyl, C ２ ~C ８ Substituted alkenyl, C ２ ~C ８ Alkynyl, C ２ ~C ８ Place Substituted alkynyl, C ３ ~C ８ Cycloalkyl, C ３ ~C ８ substituted cycloalkyl, phenyl, is selected from the group consisting of substituted phenyl, benzyl, and substituted benzyl; or R ７ and R ８ are covalently bonded together and are saturated or unsaturated C ３ ~C ８ Heterocycloar Kill or C ３ ~C ８ It may form a substituted heterocycloalkyl group; Any heterocyclic ring may contain up to three heteroatoms selected from the group consisting of O, N and S. may contain or a tautomer or salt thereof.

2. R １ is C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, C ２ ~C ８ Alkynyl, C ２ ~C ８ Substituted alkynyl, C ３ ~C ８ Cycloalkyl, C ３ ~C ８ Substituted cycloalkyl, 2. The aryl group of claim 1, wherein the aryl group is selected from the group consisting of phenyl, substituted phenyl, benzyl and substituted benzyl. The compound according to claim 1,

3. R １ is selected from the group consisting of benzyl and substituted benzyl. thing.

4. R ２ and R ５ The compound according to any one of claims 1 to 3, wherein both are hydrogen.

5. R ３ and R ４ are independently halogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted Alkyl and C １ ~C ８ 5. The compound of claim 4, wherein the compound is selected from the group consisting of alkoxy.

6. R ３ and R ４ Both are CH ３ 6. The compound of claim 5,

7. R ４ and R ５ The compound according to any one of claims 1 to 3, wherein both are hydrogen.

8. R ２ and R ３ are independently halogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted Alkyl and C １ ~C ８ 8. The compound of claim 7, selected from the group consisting of alkoxy.

9. R ２ and R ３ Both are CH ３ 9. The compound of claim 8, wherein

10. Each R ７ and R ８ are independently hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ substituted alkyl, C ２ ~C ８ Alkenyl, C ３ ~C ８ Cycloalkyl, phenyl, substituted phenyl, benzyl The compound according to any one of claims 1 to 10, which is selected from the group consisting of substituted benzyl and substituted benzyl. Compound.

11. R ６ is hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl, thiol, alkylthio The compound according to any one of claims 1 to 11, wherein the compound is selected from the group consisting of alkylthio and substituted alkylthio. The compounds listed above.

12. A compound according to any one of the compounds in Table 1.

13. A phytologically acceptable amount of any one of formula I or any one of claims 1 to 12. A fungicidal composition comprising a compound as described and a carrier.

14. The carrier is one or more of a thickener, an emulsifier, a rheological agent, a dispersant, and a polymer; The composition of claim 13.

15. A method for controlling fungal attack on a plant, comprising the steps of: The soil adapted to support the growth of the plant, the roots of the plant and the leaves of the plant are then placed in a botanically acceptable medium. with a compound according to any one of formula I or any one of claims 1 to 14 in an amount sufficient to A method that includes touching.

16. A compound according to any one of formula I or claims 1 to 14 for use in controlling fungal pathogens. A compound according to any one of claims 1 to 4.

17. The fungal pathogen is Zymoseptoria tritici. ici), Cochliobolus sativus, Puccinia triticina, Puccinia sto Puccinia striiformis, Venturia inaekua Squirrel (Venturia inaequalis), Ustilago maydis lago maydis, Uncinula necator ), Rhynchosporium commune , Magnaporthe grisea, Phakopsora Pachyrhizi (Phakopsora pachyrhizi), Parastagonospora nodo Parastagonospora nodorum, Glomerella lagenariu Glomerella lagenarium, Cercospora beticola cospora beticola, Alternaria solani solani), Pyrenophora teres, Blumeria graminis f.sp tritici), Blumeria graminis hordei (Blumeria gr aminis f. sp. hordei, Erysiphe sikoracearum he cichoracearum, Fusarium viruliforme m virguliforme, Rhizoctonia solani (Rhizoctonia s olani), Pythium ultimum and Botrytis 17. The plant according to claim 16, wherein the plant is one of Botrytis cinerea. Compound.

18. The following diseases caused by the fungal pathogens: wheat leaf spot (Zymoceptoria tritici ( Zymoseptoria tritici), barley spot disease (Cochriobolus sativus), wheat leaf rust (Pusini Puccinia triticina), yellow rust (Puccinia Puccinia striiformis, apple scab (Venturia inaequalis), Tomo blister disease of locosi (Ustilago maydis), Grape powdery mildew (Uncinula necator), Barley leaf spot (Rhynchosporium commune) omune), rice blast disease (Magnaporthe grisea grisea), Asian soybean rust (Phakopsora pachyrhizi ra pachyrhizi), wheat gall blight (Parastagonaspora nodorum) (Parastagonaspora nodorum), anthracnose of Cucurbitaceae plants (Glo Glomerella lagenarium, fluviatilis Leaf spot disease (Cercospora beticola), Summer blight of the corn (Alternaria solani), Barley net blotch (Pyrenophora teres), Powdery mildew of wheat (Blumeria graminis var. tritici) minis f. sp. tritici), powdery mildew of barley (Brumeria graminearum Blumeria graminis f.sp.hordei )), powdery mildew of Cucurbitaceae plants (Erysiphe cicoracearum choracearum), Sudden Death Syndrome of Soybean (Fusarium viruliforme ( Fusarium virguliforme), neck rot or wilt of seedlings ( Rhizoctonia solani), root rot (Pythium Ultimum (Pythium ultimum), Gray mold (Botrytis cinere 17. The compound according to claim 16, which is used to treat one of the following diseases: thing.

19. A composition for use in controlling fungal pathogens, comprising a botanically acceptable amount of: A compound according to any one of formula I or any one of claims 1 to 18, comprising a carrier. composition.

20. The fungal pathogen is Zymoseptoria tritici. ici), Cochliobolus sativus, Puccinia triticina, Puccinia sto Puccinia striiformis, Venturia inaekua Squirrel (Venturia inaequalis), Ustilago maydis lago maydis, Uncinula necator ), Rhynchosporium commune , Magnaporthe grisea, Phakopsora Pachyrhizi (Phakopsora pachyrhizi), Parastagonospora nodo Parastagonospora nodorum, Glomerella lagenariu Glomerella lagenarium, Cercospora beticola cospora beticola, Alternaria solani solani), Pyrenophora teres, Blumeria graminis f.sp tritici), Blumeria graminis hordei (Blumeria gr aminis f. sp. hordei, Erysiphe sikoracearum he cichoracearum, Fusarium viruliforme m virguliforme, Rhizoctonia solani (Rhizoctonia s olani), Pythium ultimum and Botrytis 20. The plant according to claim 19, which is one of Botrytis cinerea. Composition of.

21. The following diseases caused by the fungal pathogens: wheat leaf spot (Zymoceptoria tritici ( Zymoseptoria tritici), barley spot disease (Cochriobolus sativus), wheat leaf rust (Pusini Puccinia triticina), yellow rust (Puccinia Puccinia striiformis, apple scab (Venturia inaequalis), Tomo blister disease of locosi (Ustilago maydis), Grape powdery mildew (Uncinula necator), Barley leaf spot (Rhynchosporium commune) omune), rice blast disease (Magnaporthe grisea grisea), Asian soybean rust (Phakopsora pachyrhizi ra pachyrhizi), wheat gall blight (Parastagonaspora nodorum) (Parastagonaspora nodorum), anthracnose of Cucurbitaceae plants (Glo Glomerella lagenarium, fluviatilis Leaf spot disease (Cercospora beticola), Summer blight of the corn (Alternaria solani), Barley net blotch (Pyrenophora teres), Powdery mildew of wheat (Blumeria graminis var. tritici) minis f. sp. tritici), powdery mildew of barley (Brumeria graminearum Blumeria graminis f.sp.hordei )), powdery mildew of Cucurbitaceae plants (Erysiphe cicoracearum choracearum), Sudden Death Syndrome of Soybean (Fusarium viruliforme ( Fusarium virguliforme), neck rot or wilt of seedlings ( Rhizoctonia solani), root rot (Pythium Ultimum (Pythium ultimum), Gray mold (Botrytis cinere 20. The composition according to claim 19, which treats one of the following diseases: thing.

22. The diseases include wheat leaf spot, barley leaf spot, wheat leaf rust and Asian soybean leaf spot. The composition of claim 19, which is one of the diseases.

23. A phytologically acceptable amount of any one of formula I or any one of claims 1 to 12. Seeds treated with the compounds indicated.

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