Fungicidal arylamidines

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 the patent application Ser. No. 10 / 199,494, filed on Dec. 1, 2002, which is expressly incorporated herein by reference. To be incorporated. [Background technology]

[0002] Fungicides protect and control plants against damage caused by agriculturally 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 fungicides 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 arylamidines and their use as fungicides. may provide protection against Ascomycetes, Basidiomycetes, Imperfectiycetes and Oomycetes.

[0004] One embodiment of the present disclosure is a compound of formula I: [ka] (In the formula, R 1 represents 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 hetero Selected from the group consisting of phenyl, phenyl, substituted phenyl, benzyl and substituted benzyl be; 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 represents 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 is selected from the group consisting of thio; or R 6 and R 7 are covalently bonded together and form a saturated or unsaturated C3-C8 heterocycloalkane. may form an alkyl or C3-C8 substituted heterocycloalkyl group; Each R 7 and R 8 are independently hydrogen, C1-C8 alkyl, C1-C8 substituted alkyl, C C2-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 an alkyl or 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 producing a plant extract comprising the compound described above and a phytologically acceptable carrier material. 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 plants. A fungicidally effective amount of one or more of the compounds described above is applied to at least one fungus, seed, plant and The method may include a method comprising applying to an area adjacent to a plant.

[0007] The following terms may include generic "R" groups within their definitions, e.g., "the term A" It will be understood by one 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 not intended to be limiting unless otherwise specified. It is to be understood that the substitutions in formula I are not intended to be limiting or are limited by the substitutions in formula I. It is also understood that it should not be.

[0008] The term "alkyl" refers to a branched, unbranched, or saturated acyclic 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, aryl, 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, butyl It refers to aryl and pentynyl.

[0011] The term "cycloalkenyl" refers to a mono- 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, tetrahydro It refers to naphthyl, hexahydronaphthyl and octahydronaphthyl.

[0012] The term "cycloalkyl" refers to a mono- 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 and bicyclo[2.2.2]octyloxy.

[0014] The terms "aryl" and "Ar" refer to any aromatic monocyclic ring containing 0 heteroatoms. or bicyclic, for example, phenyl and naphthyl.

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

[0016] The term "heterocycloalkyl" refers to a group consisting of carbon and hydrogen atoms and one or more heteroatoms. "Aromatic rings" 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: F, Cl, Br, and I. Refers to halogen atoms.

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

[0022] The term "thiol" refers to an --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., diastereoisomers. It is to be understood that stereomers, enantiomers and mixtures thereof are also included. 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 those skilled 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 plant tissues. protection of plants against attack by plant pathogenic organisms, including application to the leaves and / or roots. Use of compounds of formula I for the protection or treatment of plants infested by phytopathogenic organisms be.

[0028] Additionally, another embodiment of the present disclosure provides a method for preparing a plant extract comprising a compound of Formula I and a phytologically acceptable carrier material. and / or to protect plants against attack by plant pathogenic organisms, including The composition is useful for treating plants infested with phytoplankton. DETAILED DESCRIPTION OF THE INVENTION

[0029] The compounds of the present disclosure can be administered in any of a variety of known techniques as compounds or formulations containing compounds. For example, the compounds can be applied to a variety of plants without damaging the commercial value of the plant. The material may be applied to the roots or foliage of plants for fungal control. For example, they can be applied in any form, such as a liquid, dust, wettable powder, flowable powder or emulsifiable concentrate.

[0030] Preferably, the compounds of the present disclosure are prepared by dissolving one or more compounds of Formula I in a phytologically acceptable carrier. Concentrated formulations are applied in the form of formulations containing water or other liquids for application. The formulation may be in the form of a powder or granules, which can then be further processed. The formulations can 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 formulation is applied as an aqueous suspension or emulsion. Such suspensions or emulsions are usually prepared by dissolving solids, known as wettable powders, in water. from aqueous, water-suspendable or emulsifiable preparations; or usually as emulsions, aqueous suspensions or suspensions As will be readily appreciated, the antifungal properties of these compounds can be readily understood. These compounds may be used in combination as long as they produce the desired utility without significantly interfering with their activity 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 weight percent, based on the total weight of In preparing wettable powder formulations, the compound may be present in an amount of from 5 to about 75 weight percent. The materials used are pyrophyllite, talc, chalk, gypsum, fuller's earth, tonite, attapulgite, starch, casein, gluten, montmorillonite clay In such an operation, the mixture may be blended with any finely divided solids such as diatomaceous earth, purified silicates, etc. The fine carrier and surfactant are typically blended with the compound and milled.

[0033] The emulsion of the compound of Formula I may comprise from about 1 weight percent to about 50 weight percent based on the total weight of the emulsion. The compound may be contained in a suitable liquid at a convenient concentration, such as a water-miscible solvent. or a mixture of a water-immiscible organic solvent and an emulsifier. The emulsion can be diluted with water and oil to form a spray mixture in the form of an oil-in-water emulsion. Useful organic solvents include petroleum aromatics such as heavy aromatic naphtha, especially 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 can be readily determined by one skilled in the art and include a variety of Suitable nonionic, anionic, cationic and amphoteric emulsifiers or blends of two or more emulsifiers Examples of nonionic emulsifiers useful in preparing emulsions include polyalkylene glycols, Cholesterol ethers, alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or Condensation products of fatty acids and ethylene oxide, ethoxylated alkylphenols, etc. Carboxylic acid esters solubilized with olefin oxides and polyols or polyoxyalkylenes 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 polyglycol ethers Suitable salts of glycol ethers are included.

[0035] Representative organic liquids that can be used to prepare emulsions of the compounds of the present disclosure include xylene, propyl alcohol, Aromatic liquids such as benzene fractions; or mixed naphthalene fractions, mineral oil, dioctyl phthalate, etc. Any substituted aromatic organic liquids; kerosene; n-butyl ether of diethylene glycol, ethyl ether various fats such as methyl ether of triethylene glycol, methyl ether of triethylene glycol Dialkylamides of acids, especially dimethylamides of fatty glycols and glycol derivatives, Petroleum fractions or hydrocarbons such as oil, aromatic solvents, paraffin oil; soybean oil, rapeseed oil, olive oil Rubbish oil, castor oil, sunflower seed oil, palm oil, corn oil, cottonseed oil, linseed oil, parsley oil Vegetable oils such as 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 include: , xylene and propylbenzene fractions, with xylene being the most prevalent in some cases. Also preferred are surfactant dispersants, 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 conjunction 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 one or more water-insoluble compounds of Formula I dispersed in an aqueous vehicle. Suspension agents are prepared by finely grinding one or more compounds and dissolving the ground material in water and the same suspensions as those discussed above. The mixture is prepared by vigorously mixing in a vehicle composed of surfactants 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. may 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 formulated in an amount of about 0.5 to about 10 parts by weight based on the total weight of the granule formulation. The compound of quinone is used in the preparation of attapulgite, bentonite, diatomaceous earth, clay or similar inexpensive materials. 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 the compound is dispersed in an amount of about 0.5 to about 100 ml. It is prepared by application to a granular carrier preformed to a suitable particle size in the range of 3 mm. Suitable solvents are those in which the compound is substantially or completely soluble. A dough or paste of the carrier, compound and solvent is made, crushed and dried to form the desired granular particles. It can also be prepared by obtaining

[0038] Dusts containing compounds of formula I may be prepared by incorporating one or more compounds in powder form, for example, kaolin clay, It can be prepared by intimately mixing with a suitable powdered 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 and wetting of the compound to target crops and organisms. These co-surfactants may optionally be used as ingredients in the formulation or in the tank. The amount of co-surfactant is typically based on the amount of water applied. Generally, it 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 amines, 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 alkyl Anionic surfactant blend; C9-C 11 Alkyl polyglycosides; Phosphated alkyl Alcohol ethoxylate; Natural primary alcohol (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 ammonium 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 that 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 purpose. 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 combination with one or more fungicides 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 can be applied in combination with other fungicides or sequentially with other fungicides. The agents include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenanthroline, ol, 8-hydroxyquinoline sulfate, ametoctrazine, aminopyrifen, Misulbrom, antimycin, Ampelomyces kiskaris quisqualis, azaconazole, Bacillus subtilis s subtilis), Bacillus subtilis s) Strain QST713, benalaxyl, benomyl, benzalbalicarb isopropyl, benzalbaicarb 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, clazafenone, 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 ethylenebis(dithiocarbamate), Lofluanid, dichlorophen, diclocymet, diclomedine, dicloran, Diethoff Encarb, difenoconazole, difenzoquat ion, diflumetrim, dimethicone Morph, Dimoxystrobin, Diniconazole, Diniconazole-M, Zinobuton, Zino Cup, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine Free base, edifenphos, enestrobin, enestrobrin, 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 Oloimide, fluoxapiproline, fluoxastrobin, fluquinconazole, flu Silazole, flusulfamide, flutianil, flutolanil, flutriafol, flu Xapyroxad, folpet, formaldehyde, fosetyl, fosetyl aluminum, Veridazole, furalaxyl, furametpyr, guazatine, guazatine acetate, GY -81, hexachlorobenzene, hexaconazole, hymexazole, imazalil, ima Zalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate ate, iminoctadine tris (albesilate), impilfluxam, iodocarb, Ipconazole, ipfenpyrazolone, iprove Nphos, iprodione, iprovalicarb, isofetamide, isoflucipram, isoprenaline Lothiolane, Isopyrazam, Isotianil, Kasugamycin, Kasugamycin Hydrochloride Hydrate substance, kresoxim methyl, laminarin, mancopper, mancozeb, mandipropamide, Maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, dichlorodibenzofuran Mercury 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, Nitrotarisopropyl, Nuari Mol, octilinone, ofurace, oleic acid (fatty acid), orysastrobin, oxadix Sil, oxathiapiprolin, oxine copper, oxpoconazole fumarate, oxycal Voxin, pefurazoate, penconazole, pencycuron, penflufen, pentac 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, pyraziflumide, pyrazophos, Ribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyrrophenone Chiron, Quinoclamine, Quinoxyfen, Quintozene, Raynautria sacharinensis (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 tridemorph, trifloxystrobin, triflumizole, triforine, tritico Nazole, validamycin, valifenalate, valifenal, vinclozolin, gine 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)-succinic acid Imide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroethylene Oroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitro propane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2, 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-dimethylphenyl)- (tropop-1-enyl)phenylthiocyanate, ampropylphos, anilazine, Dithiram, Barium Polysulfide, Bayer 32394, Benodaniol, Benquinoc benzamacryl isobutyl, benzam ... Acrylic acid, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium Mium Calcium Copper Zinc Chromate Sulfate, Carbamorph, CECA, Chlorobenzate Azone, chloraniformethane, chlorphenazole, chlorquinox, climbazole , Copper bis(3-phenylsalicylate), Copper zinc chromate, Cumoxistrobin, Khura Neb, hydrazinium cupric sulfate, cuprobam, cyclafuramide, Cipendazole, cyproflam, decaphentin, diclobenthiazox, dicloron, di Chlozolin, diclobutrazol, dimethirimol, dinocton, dinosulfone, dinote Rubon, Dipimethitron, Dipyrithione, Ditalinphos, Dodisin, Drazoxolone, E BP, enoxastrobin, ESBP, etaconazole, etem, ethilim (ethirim), phenaminestrobin, fenaminosulf, fenapanil, phenytoin Tropane, fenpicoxamide, flurylpicoxamide, flufenoxystrobin, Luopimomide, fluorotrimazole, flucarbanil, fluconazole, fluconazole Lu-cis, Flumecyclox, Furofanate, Gliodin, Griseofulvin, Hala Clinart, Hercules 3944, Hexylthiophos, ICIA0858, Ip Fentrifluconazole, ipflufenoquin, isopamphos ), isovaledion, mandestrobin, mebenil, mecarbinzide, mefentriflu Conazole, metazoxolone, metofloxam, methylmercuric dicyandiamide, metsul Hobax, Methyltetraprole, Milneb, Mucochloric Anhydride, Mikrozolin, N -3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide , natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel bis (dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, Phenylmercuric nitrate, phosdifen, prothiocarb; prothiocarb hydrochloride, pyracarb Lid, pyrapropoin, pyridaclomethyl, pyridinitrile, pyrisoxazole, pyroxazole Ciclor, Piroxiflur, Quinacetoll; Quinacetoll sulfate, Quinazamide, Quinconazo ol, quinofumelin, rabenzazole, salicylanilide, SSF-109, sultrope Tecoram, Thiazifluor, Thiofen, Thiochlorfenfim, Thiofane thioquinox, thioximide, triamiphos, triarimol, triazbutyl , triclamid, triclopyricarb, triflumezopyrim, urbaci d), zaliramide and any combination thereof.

[0042] In addition, the compounds described herein can be applied to the present invention in the medium selected for application. Insecticides, nematicides, and the like that 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 Formulating the product with other pesticides, tank-mixing with other pesticides, or It can be applied sequentially with other pesticides. Typical pesticides include 1,2-dimethicone, Chloropropane, abamectin, acephate, acetamiprid, acetion, 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, Navasin, Atidathion, Azadirachtin, Azamethiphos, Azinphos-ethyl, Azinpho Smethyl, azotoate, barium hexafluorosilicate, bartholin, bendiocarb , benfuracarb, bensultap, benzpyrimoxane, beta-cyfluthrin, beta Tercypermethrin, bifenthrin, bioalentrin, bioethanomethrin, biope Lumethrin, bistrifluron, borax, boric acid, broflanilide, bromfenbinfo Bromocyclen, Bromo-DDT, Bromophos, Bromophos-ethyl, Buphen Carb, buprofezin, butacarb, butathiophos, butocarboxim, butonate, Butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide, chlorinated camphor phene, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbofuran Enothion, carbosulfan, cartap, cartap hydrochloride, chlorantranilipro chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform chlormethicone hydrochloride, chlorethoxyphos, chlorfenapyr, chlorfenvinphos, chlor Fluazuron, chlormephos, chloroform, chloropicrin, chloroprallethrin, Chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl, Lorthiofos, chromafenozide, cinerin I, cinerin II, cinerins, cysmet Phosphorus, cloethocarb, closantel, clothianidin, copper acetoarsenite, copper arsenate, naphtha Copper oleate, copper coumaphos, coumitoate, crotamiton, crotoxyphos, Sulfonate, cryolite, cyanofenphos, cyanophos, cyantoate, cyanthrani Liprole, cyclaniliprole, ciclethrin, cycloprothrin, cyfluthrin, cy Halodiamide, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, cythioa DDT, Decarbofuran, Deltamethrin, Demefion, Demefion-O, Demefion-O Mefion-S, Demeton, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methyl sulfone, Diafenthiu Ron, Dialifos, Diatomaceous Earth, Diazinon, Dicapton, Diclofenthion, Diclo Ruvos, dichloromethiazol, dicresyl, dicrotophos, dicyclanil, dieldrin , Diflubenzuron, Dirol, Dimefluthrin, Dimefox, Dimethane, Dimethoate Dimethrine, Dimethylvinphos, Dimethylan, Zinex, Zinex Zinex 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-monfluorotrin, Esdepalesri , esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, Ethoate-methyl, Ethoprophos, Ethyl Formate, Ethyl-DDD, Ethylenediamine Romide, ethylene dichloride, ethylene oxide, etofenprox, etrimphos , EXD, Famfur, Fenamiphos, Fenazaflor, Fenchlorphos, Feneta carb, fenfluthrin, fenitrothion, fenobucarb, fenoxacrim, Fenoxycarb, fenpyrithrin, fenpropathrin, fensulfothion, fen Thione, Fenthion-ethyl, Fenvalerate, Fipronil, Flumetquin, Flumethicone Nikamide, fluazaindolizine, flubendiamide, flucofuron, flucycloxro Flucythrinate, Fluensulfone, Flufenerim, Flufenoxuron, Flu Fenprox, Flufiprole, Fluhexafon, Flupyradifurone, Flupirimi fluvalinate, fluxametamide, fonofos, formetanate, formetanane Formparanate hydrochloride, Formothion, Formparanate, Formparanate hydrochloride, Fosmetiran, Hospirate, Hostietan, Furathiocarb, Frethrin, Gamma-Cyhalothrin, Ga Nma-HCH, Halfenprox, Halofenozide, HCH, HEOD, Heptachlor Heptafluthrin, Heptenphos, Heterofos, Hexaflumuron, HHDN, Hydro Lamethylnon, hydrogen cyanide, hydroprene, hikincarb, imidacloprid, imip Lothrin, Indoxacarb, Iodomethane, IPSP, Isazophos, Isobenzane, Isopropyl Isocarbophos, 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, Kelle Van, Kinoprene, Lambda-Cyhalothrin, Lead Arsenate, Lepimectin, Leptophos, Linda lilimfos, lufenuron, ritidathion, malathion, malonoven, magidox , mecarbam, mecarfone, menasone, meperfluthrin, mefosfolan, mercurous chloride , mesulfenphos, metaflumizone, methacrifos, methamidophos, methidathion, me Thiocarb, methoclotophos, methomyl, methoprene, methoxychlor, methoxypheno Methyl bromide, methyl isothiocyanate, methyl chloroform, methylene chloroform Lid, Metofluthrin, Metolcarb, Metoxadiazone, Mevinphos, Mexacarb Milbemectin, milbemycin oxime, mipafox, mirex, morosulta Molosultap, Momfluorotrin, Monocrotophos, Monomehypo, Monosultap, morphothion, moxidectin, naphthalophos, naled, naphthalene, Nicotine, nifluridide, nitenpyram, nithiazine, nitrilacarb, novaluron, Biflumuron, omethoate, oxamyl, oxazosulfil, oxydemeton-methionine chlorine, 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 Pirimicarb, Pirimiphos-ethyl, Pirimiphos-methyl, Potassium arsenite, Thiocyanin Potassium citrate, pp'-DDT, prallethrin, precocene I, precocene II, precocene Cosene III, Primidophos, Profenofos, Profluthrin, Promacyl, Promeca Lubu, propafos, propetamphos, propoxur, prothidathion, prothiofos, Lotoate, Protrifenbut, Piflubumid, Pyraclofos, Pyrafluprole, Pi Lazophos, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrin, pyridaben, Pyridalyl, pyradaphenthion, pyrifluquinazone, pyrimidifen, pyriminostro Bin, Pirimitate, Pyriprole, Pyriproxyfen, Cassia, Quinalphos, Quinal Fos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Riania, Sabaji La, Schradan, 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-fluvalinate, tazimcarb, T DE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, teflu Torin, Temephos, TEPP, Teralethrin, Terbufos, Tetrachlorantranilipro tetrachloroethane, tetrachlorovinphos, tetramethrin, tetramethylfluro thiacloprid, 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, trialasen, Riazamate, triazophos, trichlorfon, trichlormethaphos-3, trichloro Triflumezopyrim, Triflumuron, Trimethacarb, Triphenofos, Triflumezopyrim, Triflumuron, Trimethacarb, Triflumezopyrim ... Prene, cyclopyrazoflor, vamidothion, vaniliprole, XMC, xylylcarb , zeta-cypermethrin, zolaprophos, and any combination thereof. Not limited to these.

[0043] In addition, the compounds described herein can be applied to the present invention in the medium selected 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 plants. When used in conjunction with, the compounds claimed herein are formulated with or used as herbicides. It can be tank-mixed with the herbicide or applied sequentially with the herbicide. These include 4-CPA; 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4- DB;3,4-DB;2,4-DEB;2,4-DEP;3,4-DP;2,3,6-T BA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, acyl Ronifen, acrolein, alachlor, allidochlor, alloxydim, allylal Cole, Arolac, Ametridione, Ametrine, Amivudine, Amicarbazone, Ami Dosulfuron, aminocyclopyrachlor, aminopyralid, amiprophosmethyl, ami Trol, ammonium sulfamate, anilofos, anisrone, ashram, atra Ton, atrazine, azafenidin, azimsulfuron, aziprothrin, burban, B CPC, beflubutamide, beflubutamide-M, benazolin, bencarbazone, benflu Larin, Benfuresate, Bensulfuron, Bensulide, Bentazon, Benzadox, Be Nzfendizone, benzipram, benzobicyclon, benzofenap, benzofluo benzoylprop, benzthiazuron, bicyclopyrone, bifenox, virana Phos, Bispyribac, Bixlozone, Borax, Bromacil, Bromobonyl, Bromo Butide, bromofenoxime, bromoxynil, brompyrazone, butachlor, butaf Butenacil, butamifos, butenachlor, butidazole, buthiuron, butralin, buto Roxydim, Buturon, Butyrate, Cacodylic Acid, Cafenstrole, Calcium Chlorate Calcium cyanamide, camphendichlor, carbaslam, carbetamide, carboxyl Sasol chlorprocarb, carfentrazone, CDEA, CEPC, chlormethoxyfen 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, cliodinate, clodinafop , clofop, clomazone, clomeprop, cloprop, cloproxydim, clopi Ralido, chloransulam methyl, CMA, copper sulfate, CPMF, CPPC, Cledazin, Resole, cumyluron, cyanatrin, cyanazine, cycloate, cyclopyranyl, cyclohexyl Chlopirimorate, cyclosulfamuron, cycloxydim, cyclouron, cyhalofop , Cypercort, Ciprazine, Ciprazole, Cypromid, Diamron, Dalapon, Da Zomet, Delachlor, Desmedipham, Desmetrin, Diallate, Dicamba, Di Chlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop -P, diclofop, diclosulam, dietamcort, dietatyl, diphenopentene, Difenoxuron, Difenzocort, Diflufenican, Diflufenzopyr, Zimef Ron, dimepiperate, dimethachlor, dimethametrin, dimethenamid, dimethenamid -P, Dimexano, Dimidazon, Dinitramine, Dinophenate, Dinoprop, Ginosa Mu, dinoseb, dinoterb, diphenamide, dipropetrine, diquat, disul, dithi Opir, diuron, DMPA, DNOC, DSMA, EBEP, eglinadin, endota ol, epronaz, EPTC, ervon, esprocarb, ethalfluralin, ethamez Lufron, Ethidimuron, Ethiolate, Ethofumesate, Ethoxyfene, Ethoxys Lufron, Ethinophen, Etonipromide, Etobenzanide, EXD, Fenashlam, Fenoprop, fenoxaprop, fenoxaprop-P, fenoxasulfone, Fenquinotrione, Fenteracol, Fentiaprop, Fentrazamide, Fenquinotrione Nuron, ferrous sulfate, Flamprop, Flamprop-M, Flazasulfuron, Floras Rum, Florpilauxifen, 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, flurtamon, fluthiaset, fomesafen, foramsulfuron, fosamine, 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, Offensulfuron, Ioxynil, Ipazine, Ipfencarbazone, Iprimidam , isocarbamide, isosyl, isomethiozine, isonoruron, isopolinate, isop Loparin, isoproturon, isouron, isoxaben, isoxachlorthor, isoxaben Saflutol, Isoxapirifop, Carbutilate, Ketospiradox, Rancotri On, lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA- Thioethyl, MCPB, Mecoprop, Mecoprop-P, Medinoterb, Mefenacet mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamiphos metamitron, metazachlor, metazosulfuron, metoflurane, methabenzyl Azulon, methalproparin, methazole, methiobencarb, methiozolin, methiouro Methameton, metoprothrin, methyl bromide, methyl isothiocyanate, methyl dye Muron, metobenzuron, metobromuron, metolachlor, metoslam, metoxuron , metribuzin, metsulfuron, molinate, monalid, monisouron, monochloroacetic acid Acid, Monolinuron, Monuron, Morphamcoat, MSMA, Naproanilide, Nap Lopamide, Napropamide-M, Naptalam, Nebron, Nicosulfuron, Nipiraclofe Nitralin, Nitrofen, Nitrofluorfen, Norflurazon, Norlon, O CH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin , oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxazid 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, procyazine, prodiamine, proflua Zol, 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, pyrazosulfuron Zoxifen, pyribenzoxim, pyributicarb, pyrichlor, pyridafol, pyride ate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxas Luhon, piroxsulam, quinclorac, quinmerac, quinoclamine, quinonamide, Quizalofop, Quizalofop-P, Rodetanil, Rimsulfuron, Saflufenacil, S -Metolachlor, sebutylazine, secbumeton, sethoxydim, siduron, simazine , Simeton, Simetryne, SMA, Sodium arsenite, Sodium azide, Sodium chlorate Um, Sulcotrione, Sulfate, Sulfentrazone, Sulfometuron, Sulfo Sulfuron, sulfate, sulglicapin, SWEP, TCA, tebutam, tebuthiuron, te Furiltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Ter Buchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor thiazol, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazonone Thifensulfuron, Thiobencarb, Thiafenacil, Thiocarbazil, Thioc Lorim, tolpiralate, topramezone, tralkoxydim, triafamone, triare acetone, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Trifludimoxazine, Trif Luralin, Triflusulfuron, Triphop, Trifopsim, Trihydroxytriazine , trimeturon, tripropindan, tritac, tritosulfuron, vernolate and These include, but are not limited to, xylachlor.

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

[0045] In another embodiment of the present 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 modes of action (MoA) (e.g., compositional mixtures) The compounds 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 (e.g., in a compositional mixture or simultaneously or sequentially in an application).

[0047] In another embodiment, Formula 1 is a feeding inhibitor, 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] ​​​​​​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 to X2:Y2, where X and Y are defined above.

[0054] In one embodiment, the range of the weight ratio can be X1:Y1 to 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 [[ID=2​​​​​​​​​​​​​​​​​​​​​​​​​​ 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, particularly in agricultural applications. Many of the compounds are particularly useful for use on agricultural and horticultural plants.

[0059] The efficacy of the compound against the aforementioned fungi establishes the general utility of the compound as a fungicide. 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 Leaf blight (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 (Rhynchosporium commune (Rhyn chosporium commune), rice blast disease (Magnaporthe grisea (Magnaporthe grisea), soybean rust (Phakopsora pachyrii) Phakopsora pachyrhizi), wheat blight (parasta Parastagonospora nodorum, com Powdery mildew of oak (Blumeria graminis var. speciale) inis f.sp.tritici), powdery mildew of barley (Blumelia gourami) Varnish-species hordei (Blumeria graminis f.sp.hordei) ), powdery mildew of Cucurbitaceae plants (Erysiphe cicolacearum horacearum), anthracnose of cucurbits (Glomerella lagenarium (Glom erella lagenarium), leaf spot disease of turnip (Cercospora beticola Cercospora beticola), tomato late blight (Alternaria solani (Alternaria solani), barley spot (Cochliobolus Cochliobolus sativus) and barley net blotch (Pi The pathogen Pyrenophora teres may be mentioned. The exact amount of active material applied will depend on the particular active material being applied. 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 that is contacted with the compound. and formulations containing it are equally effective at similar concentrations or against the same fungal species. There may not be any.

[0061] The compounds are disease-suppressing and effective for application to plants in botanically acceptable amounts. The term "disease-inhibitory 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 kills or inhibits 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, 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 departing from the effect sought. The present invention may be readily expanded or modified in any way, as would be apparent to one skilled in the art having the benefit of the teachings herein. .

[0063] The compounds of formula I can be made using well-known chemical procedures. Intermediates not listed 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 arylamidine 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

[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) is the scheme 1, step a. Compounds of formula 1.1 (wherein R 2 , R 4 and R 5 is as defined initially) 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 treated 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 the first one) can be obtained. Compounds of formula 3, where R 2 , R 3 , R 4 and R 5 is defined as the first , can be prepared by the method shown in Scheme 1, step b. Compounds of formula 1.2 ( In the formula, R 2 , R 4 and R 5 is as initially defined) as shown in b As shown above, in a solvent such as 1,4-dioxane, cesium carbonate (Cs2CO3) in the presence of a base under microwave irradiation at temperatures between about 23°C and 120°C in dichloromethane and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) Catalysts such as complexes (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 as defined at the beginning) Compounds of formula 1.4 (wherein R 2 , R 3 , R 4 and R 5is defined as (which is a compound of formula 1.3) 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) to c As shown in the figure, 3:2:1 tetrahydrofuran ( Lithium hydroxide in a solvent mixture such as THF:methanol (MeOH):water (H2O) and a base such as thium (LiOH) to give compounds of formula 1.4, where R 2 , R 3 , R 4 and R 5 is as defined initially). Scheme 1 [ka]

[0066] Alternatively, a compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined first (which is as follows) can be prepared by the method shown in Scheme 2, steps d-f Compounds of formula 2.2 (wherein R 2 , R 4 and R 5 is defined as the first , can be prepared by the method shown in Scheme 2, step d. 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 approximately 0°C and 23°C as follows: with a halogenating reagent 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) to e As shown in the figure, the reaction mixture was 10:1 1,4-dioxane:water at temperatures between about 23°C and 100°C. In the presence of a base such as tripotassium phosphate (K3PO4) in a solvent mixture such as (2 -Dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (phenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methane 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 as defined at the beginning) Compounds of formula 1.4 (wherein R 2 , R 3 , R 4 and R 5 is defined as (which is a compound) 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 one) to f As shown in the figure, potassium hydroxide is easily converted into potassium hydroxide in a solvent such as water at a temperature of about 23°C to 60°C. Treatment with a base such as potassium hydroxide (KOH) affords compounds of formula 1.4, where R 2 , R 3 , R 4 and R 5 is as defined initially). Scheme 2 [ka]

[0067] Alternatively, a compound of formula 1.4, where R 2 , R 3 , R 4 and R 5 is defined first (which is as follows) can be prepared by the method shown in Scheme 3, steps g-n Compounds of formula 3.2 (wherein 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) in g As shown in the figure, sodium nitrite is reacted with acetic acid or other solvents at temperatures between about 23°C and 85°C. Treatment with hydrogen bromide (HBr) in the presence of ammonium (NaNO2) gives the compound of formula 3.2 (In the formula, R 2 , R 3 , R 4 and R 5 is as defined at the beginning) Compounds of formula 3.3 (wherein R 2 , R 3 , R 4 and R 5 is defined as (which is) 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 first) and As shown in Figure 1, 1:1 ethanol (EtOH): Ammonium chloride (NH4Cl), for example, 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 (wherein R 2 , R 3 , R 4 and R 5 is first defined as (which is the formula 3) can be prepared by the method shown in Scheme 3, Step i. 4 (wherein R 2 , R 3 , R 4 and R 5 is defined as the first As shown in Fig. 1i, N,N-dimethylformamide (D In a solvent such as MF, a halogenating reagent such as N-bromosuccinimide (NBS) is used. Upon treatment with a drug, a compound of formula 3.3 (wherein R 2 , R 3 , R 4 and R 5 is first defined Compounds of formula 3.5 (wherein R 2 , R 3 , R 4 and R 5 is as originally defined) 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 in j) under microwave irradiation as shown in In solvents such as N-methyl-2-pyrrolidone (NMP) at temperatures between 23°C and 180°C 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 Compounds of formula 3.3, wherein: , R 2 , R 3 , R 4 and R 5 is as defined initially) is denoted in k As shown in Fig. 1, tetrakis(trifluoromethyl)propanol is produced in a solvent such as DMF at a temperature of about 23°C to 120°C. In the presence of a metal catalyst such as (phenylphosphine)-palladium(0) (Pd(PPh3)4) by treatment with a metal cyanide such as zinc(II) cyanide (Zn(CN)2) to give the compound of formula 3.4 (wherein R 2 , R 3 , R 4 and R 5is as initially defined) Compounds of formula 1.4 (wherein R 2 , R 3 , R 4 and R 5 is first defined (as defined above) can be prepared by the method shown in Scheme 3, Step 1. A compound of formula 3.5 (wherein R 2 , R 3 , R 4 and R 5 is defined as ) in a solvent such as HO at a temperature of about 23-120°C, as shown in l. with a base such as potassium hydroxide (KOH) to give compounds of formula 1.4, where R 2 , R 3 , R 4 and R 5 is as originally defined). In addition, compounds of formula 3.6 (wherein R 2 , R 3 , R 4 and R 5 is defined as (which is) 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 first) and 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 initially defined) Compounds of formula 1.4 (wherein 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 one) in n As shown in Fig. 1, a 3:2:1 THF:MeOH:water mixture was used at temperatures between about 23°C and 125°C. In any solvent mixture, treatment with a base such as lithium hydroxide (LiOH) yields the compound represented by formula 1.4. wherein R 2 , R 3 , R 4 and R 5 is as defined at the beginning) 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 formula 1) can be prepared by the method shown in Scheme 4, step o. 4 (wherein R 2 , R 3 , R 4 and R 5 is defined as the first As shown in Fig. 1, 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 Peptide coupling reagents such as 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 (as initially defined) To prepare a compound of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is first defined Alternatively, a compound of formula 4.1 (where R 1 , R 2 , R 3 , R 4 and R 5 is as originally defined) in Scheme 4, step p Compounds of formula 1.4 (wherein R 2 , R 3 , R 4 Reach BiR 5 is as originally defined) 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 originally defined), to give a compound of formula 4.1, where R 1 , R 2 , R 3 , R 4 and R 5is first defined (as shown) 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 first defined (as defined above) can be prepared by the method shown in Scheme 5, step q. A compound of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is defined first As shown in q, the reaction mixture is dissolved in 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 amines such as amines of formula 5.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined initially). 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 originally defined) in the process shown in Scheme 6, steps r-s. Compounds of formula 6.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is the most and Z is an alkyl group) can be prepared in Scheme 6, step r Compounds of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is as defined at 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 group; is a methyl group) to give a compound of formula 6.1, where R 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 first defined (as shown) can be prepared by the method shown in Scheme 6, step s 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) 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, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined at the beginning) 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 is the most (as initially defined) can be prepared by the method shown in Scheme 7, step t. Compounds of formula 4.1 (wherein 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 reagent such as phosphoryl trichloride (POCl3) in a solvent such as toluene at high temperatures, In the presence of a compound of formula 7.1, 6 , R 7 and R 8 is defined as ) to give compounds of formula 7.2, where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is as defined initially). 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 first defined (as defined herein) can be prepared by the method shown in Scheme 8, steps u to v. Compounds of formula 8.1 (wherein 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 (which is a soluble form of ethanol) in 1:1 DCM:H2O, 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 as defined previously) is the scheme 8, step v. Compounds of formula 8.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is as previously defined), denoted in v Compound 6.2 (wherein R 7 Reach BiR 8 is as originally defined) 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 (wherein R 1 , R 2, R 3 , R 4 and R 5 is the most (as initially defined) can be prepared by the method shown in Scheme 9, step w. Compounds of formula 4.1 (wherein R 1 , R 2 , R 3 , R 4 and R 5 is first defined (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-HO) Treatment with trimethyl orthoformate gives compounds of formula 9.1, where R 1 , R 2 , R 3 , R 4 Reach BiR 5 is as originally defined). 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 initially defined) can be prepared by the method shown in Scheme 9, step x. Compounds of formula 9.1 (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 is defined as the first) to x As shown in the figure, the reaction mixture was 1:1 methanol:1, at temperatures between about 23°C and reflux (about 80°C). In a solvent mixture such as 4-dioxane in the presence of a base such as triethylamine to form a compound of formula 9.2, where R 7 and R 8 is as defined at the beginning) 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 as defined initially). 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 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 teeth , as originally defined) at a temperature of about 23°C to 60°C, as indicated by 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 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 First (which is defined as 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 (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 teeth, as originally defined) at a temperature of about 23° C. as shown in Iodine is produced in the presence of a base such as potassium carbonate (K2CO3) in a solvent such as toluene. and alkylating agents such as methyl methyl ether to give compounds of formula 11.1, where R 1 , R 2 , R 3 , R 4 , R 5 , R 7 and R 8 is as defined initially). 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 (wherein 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 as defined at the beginning) do. Scheme 12 [ka] [Example]

[0077] Example 1A: Preparation of methyl 4-amino-5-iodo-methylbenzoate [ka] Methyl 4-amino-2-methylbenzoate (0.29 g, 1. 76 mmol) solution, respectively, with 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 off. The crude product was triturated with EtOH (1 mL) and pentane (9 mL). Evaporation 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 slowly warm 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) and 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 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 x 50 mL). The organic layer was washed with brine (3 x 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 (400 MHz, 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 cesium carbonate (0.98 g, 3.02 mmol) in 100 mL of ethanol (0.22 g, 0.75 mmol) was ol) was added and it was degassed for 5 min. Then, PdCl2(dppf)DCM (0.06 1 g, 0.07 mmol) and trimethylboroxine (0.23 g, 1.88 mmol) was added and the reaction mixture was heated to 120° C. under microwave irradiation for 1 hour. (15 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layers were The crude product was dried over Na2SO4, filtered, and concentrated under reduced pressure. chromatography (silica gel (SiO2), 20 → 25% ethyl acetate in hexane) The product was purified by ESIM 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 tripotassium (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 extracted with DCM and purified by flash column chromatography. Purification was performed by silica gel (SiO2, 0→100% ethyl acetate in hexane). , the title compound (658 mg, 2.77 mmol, 42% yield) and 86 as a white solid. 6 mg (43%) of recovered starting material was obtained. 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-dimethylthiazolinone 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 (400 MHz, 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 chloride Methylbenzoate (0.658 g, 2.77 mmol) was dissolved / suspended in 6 M aqueous KOH solution. To the suspension was added MeOH (5 mL) at room temperature. The mixture was then heated to 60°C. The reaction mixture was cooled to room temperature, diluted with water, and adjusted to pH approx. The mixture was carefully acidified to 4-5°C. The product was extracted with EtOAc (3x). The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound ( 437 mg, 2.41 mmol, 87% yield was obtained. 1 H NMR (500 MHz, 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 (126 MHz, 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 NaNO (0.49 mmol), aqueous HBr (7.7 mL) was added 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 (400 MHz, 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- 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 The crude material was diluted with water (30 mL), filtered, and the solid was extracted with EtOAc ( The aqueous layer was extracted with EtOAc (2 x 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 mmHg) in NMP (20 mL) To a solution of CuCN (2.2 g, 24.99 mmol), the reaction mixture was cooled to 200°C. The mixture was heated to 180°C under microwave irradiation for 1.5 hours. 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 (400 MHz, 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) (12.9g , 11.25 mmol) was added and the reaction mixture was heated in a sealed tube to 120°C 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 extracted under reduced pressure. The crude product was purified by column chromatography (silica gel (SiO2), petroleum ether Purification by 15% to 20% ethyl acetate in ethanol gave the title compound (5. 7 g, 52% yield was obtained. 1 H NMR (400 MHz, 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 HCl (19 mmol) was placed in a 45 mL Parr reactor with 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 Purification by elution with 0→40% ethyl acetate in ether gave the title compound as a rose-red solid. The compound (363 mg, yield 20%) was obtained. 1 H NMR (400 MHz, 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 1.0g of KOH (6.0g, 107.52mmol) was added at room temperature, and the reaction mixture The mixture was heated in a sealed tube to 120° C. 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 mL of DCM. 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. was obtained, 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 100 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 x 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. and ethyl magnesium bromide (1M in THF, 7.49 mL, 7.49 mmol) was added dropwise over 5 minutes and the resulting solution was stirred overnight. After 18 hours, TLC showed that the starting material The reaction was diluted with saturated aqueous NH4Cl (5 The mixture was quenched with 200 mL of ethanol and extracted with diethyl ether (3 x 50 mL). The crude material was passed through a phase separator and concentrated to a clear oil. The mixture was purified by chromatography (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=7.4Hz,3H); 13 C NMR (126 MHz, 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. 2M in HF, 3.49 mL, 6.99 mmol) was added via syringe over 2 minutes. The ice bath was then removed. The reaction was stirred at room temperature. After 1 hour, TLC showed the starting material was consumed. 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) 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 allowed to slowly come to room temperature to allow the ice to melt. After 18 hours, TLC indicated consumption of the 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 (400 MHz, 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) in 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 hours. Then, the reaction mixture was poured into ice-cold water (100 mL) and Extraction with tOAc (2 x 200 mL) was performed. The combined organic layers were dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography (silica Purification by silica gel (SiO2, 10→15% ethyl acetate in hexane) gave an off-white solid The title compound (3.8 g, 55% yield) was obtained as a result. 1 H NMR (400 MHz, 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) A 20 mL vial was filled with 2-(p-tolyl)propan-2-ol (364 mg, 2.42 mL). DCM (12. 1 mL) was added, and then 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 stirred at room temperature overnight. After 18 hours, the reaction was filtered. The crude material was purified by flash column chromatography (C Purification by reverse phase (50→100% acetonitrile in water) gave the title compound as an orange oil. The compound was obtained (107 mg, 0.36 mmol, yield 30%). 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, 814 cm -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 attached to a reflux condenser, heated to 80°C, and 4 The mixture was stirred for 8 hours. After 48 hours, 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-amino-2,5-dimethylbenzoic acid 4-methylbenzyl In a solution of 100 mg (0.37 mmol) of benzoyl in 2 mL of triethyl orthoformate (12.00 The solution was dissolved in p-toluenesulfonic acid monohydrate (7.06 mg, 0. 03 mmol) was added. The reaction was heated to reflux (140°C) and stirred for 3 hours. 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 x 10 mL). The residue was redissolved in DCM (0.371 mL). Diethylamine (0.058 mL, 0.55 mmol) was added dropwise via syringe. The solution was heated to 40°C and stirred for 3 hours. 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 chloride Preparation of 4-methylbenzylbenzoate [ka] In a 20 mL vial, piperidin-2-one (0.103 mL, 1.11 m A solution of 1000 mol of phosphoryl trichloride ( 0.052 mL, 0.55 mmol) was added and the cloudy reaction was stirred at room temperature for 2 hours. 4-methylbenzyl-4-amino-2,5-dimethylbenzoate (150 mg, 0 0.55 mmol) and the reaction was fitted with a reflux condenser and heated at reflux (110 °C) for 3 h. The resulting clear, gold-colored reaction mixture was then cooled to room temperature and purified with 10% aqueous NaOH. The crude reaction was stirred overnight. The layers were separated. The aqueous layer was separated and washed with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine. , dried over Na2SO4, filtered and concentrated to an oil. SCX column (DCM, D The crude material was purified using HCl (equilibrated with MeOH). The column was loaded and flushed with DCM and MeOH to elute 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 (600 MHz, 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 (151 MHz ,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-amino-2,5-dimethylbenzoic acid 4-methylbenzyl benzol (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 to the solution via syringe. 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 a pale yellow oil. 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 2-dimethylbenzoate [ka] 2-Methyl 4-amino-2,5-dimethylbenzoate in trimethyl orthoformate (6 mL) A solution of rubenzil (0.22 g, 0.81 mmol) was refluxed at 120° C. for 16 hours. The reaction mixture was then concentrated under reduced pressure to give 0.22 g of crude HCl 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 crude material was purified by preparative HPLC and obtained as an off-white solid. The title compound (12 mg, 4% yield) was obtained. 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 m L, 4.83 mmol) was added and the reaction was heated to 60° C. and stirred overnight. The reaction was 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 extracted with DCM (3×20 No material was observed in the organic layer, and the aqueous layer was concentrated to give the crude material. The resulting solution was purified by flash column chromatography (C18 reverse phase, 10 → 90% acetonitrile in water) Purification by HPLC gave the title compound (443 mg, 1.89 mmol, 1.09 mmol) 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 (fluoromethyl)benzyl (0.050 g, 0.118 mmol) in acetone (1 To this solution was added 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 stirred for 18 hours, then diluted with ethyl acetate (50 mL) and passed through Celite. The crude material was purified by flash column chromatography (silica gel). Purification by silica gel (SiO2, 0→70% ethyl acetate in hexane) gave 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 (471 MHz, 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 FNM 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: Control of wheat leaf blight (Zymoseptoria 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 occurred. All sprayed plants were then screened for further treatment. All fungicides were tested using the methods described above unless otherwise stated. were evaluated for their activity against the target diseases.

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

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

[0107] Example C: Evaluation of fungicidal activity: Asian soybean rust (Phakopsora pachyrhizi) opsora pachyrhizi);Bayer code PHAKPA): The 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 0.0. The fungicide solution was applied to the drum using an automatic spray applicator. All sprayed plants were allowed to air dry before further handling. I did.

[0108] Soybean plants (variety "Williams 82") were placed in soilless potting medium in one pot. Plants were grown at one plant per 10-day-old seedling. Plants were inoculated as described. Plants were incubated in a dark mist chamber at 100% relative humidity for 24 hours. The fungicide formulations and applications were carried out in a controlled manner. The results were as described in Example A. When the symptoms of the disease were fully manifested, the disease severity was assessed as follows: The percentage of disease control was assessed 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 blight (Rhynchosporium secharis) nchosporium secalis); Bayer code RHYNSE): Barley plants (variety 'Harrington') were grown in soilless potting medium in a greenhouse. 7-10 seedlings per pot were grown until the first leaf fully emerged from the seeds. These plants showed signs of Rhynchosporium secharis after fungicide treatment. After inoculation, the plants were placed in a 10 The plants were 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 transferred to a greenhouse to allow disease to develop. The fungicide formulation and application was 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 the method of Test plants were infested with Cochliobolus sativus (Cochli) 24 hours after fungicide treatment. After inoculation, the plants were inoculated with a spore suspension of B. obolus sativus. The plants were then kept at a relative humidity of 100°C for 2 days to allow the spores to germinate and infect the leaves. The plants were 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 The inventions described in the original claims of this application are set forth below. (1) Formula I:

change

Claims

1. Formula I: 【Chemistry 1】 (In the formula, R １ is C ２ ~C ８ Alkenyl, C ２ ~C ８ substituted alkenyl; 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, 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 is selected from the group consisting of substituted alkoxy, thiol, alkylthio, and substituted alkylthio; or R ６ and R ７ are covalently bonded together and are saturated or unsaturated C ３ ~C ８ Heterocycloalkyl or C ３ ~C ８ 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 Substituted alkynyl, C ３ ~C ８ Cycloalkyl, C ３ ~C ８ is selected from the group consisting of substituted cycloalkyl, phenyl, 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 Heterocycloalkyl or C ３ ~C ８ 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. or a tautomer or salt thereof.

2. R ２ and R ５ and R are both hydrogen.

3. R ３ and R ４ are independently halogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl and C １ ~C ８ 3. The compound of claim 2, wherein the compound is selected from the group consisting of alkoxy.

4. R ３ and R ４ are both CH ３ 4. The compound of claim 3, wherein:

5. R ４ and R ５ and R are both hydrogen.

6. R ２ and R ３ are independently halogen, C １ ~C ８ Alkyl, C １ ~C ８ Substituted alkyl and C １ ~C ８ 6. The compound of claim 5, wherein the compound is selected from the group consisting of alkoxy.

7. R ２ and R ３ are both CH ３ 7. The compound of claim 6, wherein:

8. 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 The compound of any one of claims 1 to 7, wherein the compound is selected from the group consisting of cycloalkyl, phenyl, substituted phenyl, benzyl, and substituted benzyl.

9. R ６ is hydrogen, C １ ~C ８ Alkyl, C １ ~C ８ The compound of any one of claims 1 to 8, which is selected from the group consisting of substituted alkyl, thiol, alkylthio and substituted alkylthio.

10. A fungicidal composition comprising a phytologically acceptable amount of a compound according to any one of claims 1 to 9 and a carrier.

11. 11. The composition of claim 10, wherein the carrier is one or more of a thickener, an emulsifier, a rheological agent, a dispersant, and a polymer.

12. 10. A method of controlling fungal attack on a plant, the method comprising contacting an area adjacent to the plant, soil adapted to support the growth of the plant, the roots of the plant, and the leaves of the plant with a botanically tolerated amount of a compound according to any one of claims 1 to 9.

13. A compound according to any one of claims 1 to 9 for use in the control of fungal pathogens.

14. The fungal pathogens include Zymoseptoria tritici, Cochliobolus sativus, Puccinia triticina, Puccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium commune, Magnaporthe grisea, and the like. grisea), Phakopsora pachyrhizi, Parastagonospora nodorum, Glomerella lagenarium, Cercospora beticola, Alternaria solani, Pyrenophora teres, Blumeria graminis f.sp. tritici, Blumeria graminis f.sp. tritici, Blumeria graminis f.sp. hordei f. sp. hordei), Erysiphe cichoracearum, Fusarium virguliforme, Rhizoctonia solani, Pythium ultimum and Botrytis cinerea.

15. The following diseases caused by said fungal pathogens are: wheat leaf blight (Zymoseptoria tritici), barley leaf spot (Cochliobolus sativus), wheat leaf rust (Puccinia triticina), stripe rust (Puccinia striiformis), apple scab (Venturia inaequalis), corn blister (Ustilago maydis), grape powdery mildew (Uncinula necator), and the like. necator), barley leaf blight (Rhynchosporium commune), rice blast (Magnaporthe grisea), Asian soybean rust (Phakopsora pachyrhizi), wheat blight (Parastagonospora nodorum), anthracnose of cucurbits (Glomerella lagenarium), and leaf spot of turnip (Cercospora beticola). beticola), tomato late blight (Alternaria solani), barley net blotch (Pyrenophora teres), wheat powdery mildew (Blumeria graminis f.sp. tritici), barley powdery mildew (Blumeria graminis f.sp. hordei), cucurbit powdery mildew (Erysiphe cichoracearum), soybean sudden death syndrome (Fusarium viruliforme), virguliforme), neck rot or damping-off of seedlings (Rhizoctonia solani), root rot (Pythium ultimum)14. The compound of claim 13, which treats one of the following diseases: fungus (Bacterial blight (Bacterial blight (Bacterial rot ...

16. 10. A composition for use in the control of fungal pathogens, comprising a phytologically acceptable amount of a compound according to any one of claims 1 to 9 and a carrier.

17. The fungal pathogens include Zymoseptoria tritici, Cochliobolus sativus, Puccinia triticina, Puccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium commune, Magnaporthe grisea, and the like. grisea), Phakopsora pachyrhizi, Parastagonospora nodorum, Glomerella lagenarium, Cercospora beticola, Alternaria solani, Pyrenophora teres, Blumeria graminis f.sp. tritici, Blumeria graminis f.sp. tritici, Blumeria graminis f.sp. hordei f. sp. hordei), Erysiphe cichoracearum, Fusarium virguliforme, Rhizoctonia solani, Pythium ultimum, and Botrytis cinerea.

18. The following diseases caused by said fungal pathogens are: wheat leaf blight (Zymoseptoria tritici), barley leaf spot (Cochliobolus sativus), wheat leaf rust (Puccinia triticina), stripe rust (Puccinia striiformis), apple scab (Venturia inaequalis), corn blister (Ustilago maydis), grape powdery mildew (Uncinula necator), and the like. necator), barley leaf blight (Rhynchosporium commune), rice blast (Magnaporthe grisea), Asian soybean rust (Phakopsora pachyrhizi), wheat blight (Parastagonospora nodorum), anthracnose of cucurbits (Glomerella lagenarium), and leaf spot of turnip (Cercospora beticola). beticola), tomato late blight (Alternaria solani), barley net blotch (Pyrenophora teres), wheat powdery mildew (Blumeria graminis f.sp. tritici), barley powdery mildew (Blumeria graminis f.sp. hordei), cucurbit powdery mildew (Erysiphe cichoracearum), soybean sudden death syndrome (Fusarium viruliforme), virguliforme), neck rot or damping-off of seedlings (Rhizoctonia solani), root rot (Pythium ultimum)17. The composition of claim 16, wherein the composition treats one of the following diseases: corn rot (Corn rot, Pseudomonas aeruginosa), corn rot (Corn rot, Pseudomonas aeruginosa), and gray mold (Botrytis cinerea).

19. 17. The composition of claim 16, wherein the disease is one of wheat late blight, barley spot, wheat leaf rust, and Asian soybean rust.

20. Seeds treated with a phytologically acceptable amount of a compound according to any one of claims 1 to 9.

Images