BR102017018484A2 - 1,3-OXAZINE-2,4-DIONA COMPOUNDS WITH FUNGICIDE ACTIVITY - Google Patents

Abstract

The present invention relates to pyrido-1,3-oxazine-2,4-diones of formula I and their use as fungicides.

Description

(54) Title: PIRIDO-1,3OXAZINE-2.4-DIONA COMPOUNDS WITH FUNGICIDE ACTIVITY (51) Int. Cl .: C07D 498/02; A01N 43/90; A01N 47/24; A01P 3/00 (52) CPC: C07D 498/02, A01N 43/90, A01N 47/24 (30) Unionist Priority: 8/30/2016 US 62 / 381,282 (73) Holder (s): DOW AGROSCIENCES LLC ( 72) Inventor (s): BRANNON SAM; KEVIN MEYER; CHENGLIN YAO; BRIAN LOY; JARED RIGOLI; NICHOLAS BABIJ (74) Attorney (s): DANNEMANN, SIEMSEN, BIGLER & IPANEMA MOREIRA (57) Abstract: The present invention relates to Formula I pyrido-1,3-oxazine-2,4-diones and their use as fungicides.

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Descriptive Report of the Invention Patent for “PIRIDO-1,3-OXAZINE-2,4-DIONA COMPOUNDS WITH FUNGICIDE ACTIVITY”.

FUNDAMENTALS & SUMMARY [0001] Fungicides are compounds, of natural or synthetic origin, that act to protect and / or cure plants against damage caused by agriculturally relevant fungi. Generally, no fungicide alone is useful in all situations. As a result, research is underway to produce fungicides that can perform better, are easier to use and are cheaper. [0002] The present description refers to pyrido-1,3-oxazine-2,4diones and their use as fungicides. The compounds of the present description can offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.

[0003] One embodiment of the present description can include compounds of Formula I:

on what:

R ₁ is hydrogen or C ₁ - C ₅ alkyl, each optionally substituted by 0, 1 or multiple R ₆ ;

R2 is hydrogen, C1 - C5 alkyl or cycloalkyl, each optionally substituted by 0, 1 or multiple R ₆ ;

R3 is alkyl, cycloalkyl, aryl or heteroaryl, each optionally substituted by 0, 1 or multiple R ₆ ;

R ₄ is hydrogen, halo, hydroxyl, alkyl or alkoxy;

R ₅ is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy,

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2/48 thioalkyl, thioaryl or heterothioaryl, each optionally substituted by 0, 1 or multiple R ₆ ;

R ₆ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano or heterocyclyl, each optionally substituted by 0, 1 or multiple R ₇ ;

R ₇ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl; and

R ₈ is hydrogen or C ₁ - C ₅ alkyl, substituted by 0, 1 or multiple R ₆ . [0004] Another embodiment of the present description may include a fungicidal composition for the control or prevention of fungal attacks that comprises the compounds described above and a phytologically acceptable carrier material.

[0005] Yet another embodiment of the present description may include a method for controlling or preventing a fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more compounds described above to at least one among fungus, plant and an area adjacent to the plant.

[0006] It will be understood by those skilled in the art that the following terms may include generic R groups within their definitions, for example, the term alkoxy refers to a substituent -OR. It is also understood that, within the definitions for the following terms, these R groups are included for purposes of illustration and should not be construed as limiting or being limited by substitutions over Formula I.

[0007] The term "alkyl" refers to a branched, unbranched or saturated cyclic carbon chain, including, but not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

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3/48 [0008] The term alkenyl ”refers to a cyclic, branched or unbranched carbon chain containing one or more double bonds, including, but not limited to, ethylene, propenyl, butenyl, isopropenyl, isobutenyl, cyclobutenyl , cyclopentenyl, cyclohexenyl and the like.

[0009] The term "alkynyl" refers to a branched or unbranched carbon chain containing one or more triple bonds, including, but not limited to, propynyl, butynyl and the like.

[0010] The terms aryl ”and“ Ar ”refer to any aromatic ring, mono- or bicyclic, containing 0 heteroatom.

[0011] The term heterocyclyl ”refers to any aromatic or non-aromatic ring, mono- or bicyclic, containing one or more heteroatoms.

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

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

[0014] The term "cyan" refers to a substituent -C ^ N.

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

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

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

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

[0019] The term haloalkyl ”refers to an alkyl that is substituted by Cl, F, I or Br or any combination thereof.

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

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

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

[0023] The term thioaryl refers to a substituent -SAr.

[0024] Throughout the description, the reference to the compounds of FórPetição 870170072933, of 28/09/2017, p. 7/59

4/48 mule I will be read as also including all stereoisomers, for example, diastereomers, enantiomers and mixtures thereof. In another embodiment, Formula I is read as also including its salts or hydrates. Exemplary salts include, but are not limited to: hydrochloride, hydrobromide, hydroiodide, trifluoroacetate and trifluoromethane sulfonate.

[0025] It is also understood by those skilled in the art that additional substitution is permitted, unless otherwise noted, provided that the chemical bonding and voltage energy rules are met and the product still exhibits fungicidal activity.

[0026] Another modality of the present description is the use of a Formula I compound to protect a plant from being affected by a phytopathogenic organism or to treat a plant infested by a phytopathogenic organism, comprising the application of a Formula I compound. , or a composition comprising applying the compound to the soil, a plant, a part of the plant, foliage and / or roots.

[0027] Additionally, another embodiment of the present description is a composition useful for protecting a plant from being affected by a phytopathogenic organism and / or for treating a plant infested by a phytopathogenic organism comprising a compound of Formula I and a phytologically carrier material. acceptable.

DETAILED DESCRIPTION [0028] The compounds of the present description can be applied by any of the varieties of known techniques, as well as the compounds or formulations comprising the compounds. For example, the compounds can be applied to the roots or foliage of plants to control various fungi, without damaging the commercial value of the plants. Materials can be applied in the form of

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5/48 any of the types of formulation generally used, for example, as solutions, powders, soluble powders, dispersible concentrates or emulsifiable concentrates.

[0029] Preferably, the compounds of the present description are applied in the form of a formulation, comprising one or more of the compounds of Formula I with a phytologically acceptable carrier. Concentrated formulations can be dispersed in water or other liquids for application, or formulations can be similar to powders or granules, which can then be applied without further treatment. The formulations can be prepared according to the procedures that are conventional in the agricultural chemistry technique.

[0030] This description includes all vehicles by which one or more of the compounds can be formulated for distribution and use as a fungicide. Typically, formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions can be produced from water-soluble, water-suspended or emulsifiable formulations that are solid, generally known as soluble powders; or liquids generally known as emulsifiable concentrates, aqueous suspensions or suspension concentrates. As will be readily appreciated, any material to which these compounds can be added can be used, as long as it results in the desired utility without significant interference in the activity of these compounds as antifungal agents.

[0031] Soluble powders that can be compacted to form water-dispersible granules comprise an integral mixture of one or more of the compounds of Formula I, an inert carrier and surfactants. The concentration of the compound in the soluble powder can be from about 10 percent to about 90 percent by weight based on the total weight of the soluble powder, more preferably, about 25 percent by weight

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6/48 to about 75 weight percent. In the preparation of soluble powder formulations, the compounds can be combined with any finely divided solid, such as propylene, talc, chalk, plaster, Fuller's earth, bentonite, atapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicates or the like. In these operations, the finely divided vehicle and surfactants are typically mixed with the compound (s) and ground.

[0032] Emulsifiable concentrates of the compounds of Formula I can comprise a convenient concentration, such as from about 1 weight percent to about 50 weight percent of the compound, in a suitable liquid, based on the total weight of the concentrate. The compounds can be dissolved in an inert vehicle that is a water-miscible solvent or a mixture of water-immiscible organic solvents and emulsifiers. The concentrates can be diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions. Useful organic solvents include aromatics, especially the high boiling naphthalene and olefinic portions of oil, such as heavy aromatic naphtha. Other organic solvents can also be used, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone and complex alcohols, such as 2-ethoxyethanol.

[0033] Emulsifiers that can be used to advantage in this document can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers or a mixture of two or more emulsifiers. Examples of non-ionic emulsifiers useful in the preparation of emulsifiable concentrates include polyalkylene glycol ethers and alkyl condensation products and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as alkyl phenols ethoxylate and carboxylic esters SOPetition 870170072933, of 09/28/2017, p. 10/59

7/48 lubricated with polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulfonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts of phosphate polyglycol ether.

[0034] Representative organic liquids that can be used in the preparation of the emulsifiable concentrates of the compounds of the present description are aromatic liquids, such as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids, such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly dimethyl amides of fatty glycols and glycol derivatives, such as n-butyl ether, ethyl ether or diethylene glycol methyl ether, triethylene glycol methyl ether, petroleum fractions or hydrocarbons, such such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, flaxseed oil, palm oil , peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids can also be used in the preparation of the emulsifiable concentrate. Organic liquids include xylene and propylene benzene fractions with xylene being the most preferred in some cases. Surface active dispersing agents are typically used in liquid formulations and in an amount of 0.1 to 20 weight percent based on the combined weight of the dispersing agent with one or more of the compounds. The formulations can also contain other compatible additives, for example, plant growth regulators and other compounds

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8/48 biologically active used in agriculture.

[0035] Aqueous suspensions comprise suspensions of one or more water insoluble compounds of Formula I dispersed in an aqueous vehicle in a concentration in the range of about 1 to about 50 weight percent based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding one or more of the compounds and vigorously mixing the background material in a vehicle composed of water and surfactants chosen from the same types discussed above. Other compounds such as inorganic salts and synthetic or natural gums can also be added to increase the density and viscosity of the aqueous vehicle.

[0036] The compounds of Formula I can also be applied as granular formulations that are particularly useful for soil applications. Granular formulations generally contain from about 0.5 to about 10 weight percent based on the total weight of the granular formulation of the compound (s) dispersed in an inert vehicle that consists entirely or largely of divided inert material roughly as atapulgite, bentonite, diatomite, clay or a similar cheap substance. These formulations are generally prepared by dissolving the compounds in a suitable solvent and applying them in a granular vehicle that has been preformed to the appropriate particle size in the range of about 0.5 to about 3 mm. A suitable solvent is a solvent in which the compound is substantially or completely soluble. These formulations can also be prepared by creating a mass or paste of the vehicle and the compound and solvent and grinding and drying to obtain the desired granular particle. [0037] The powders containing the compounds of Formula I can be prepared by thoroughly mixing one or more of the compounds in powder form with a suitable powdered agricultural carrier, such as, for example, kaolin clay, ground volcanic rock and the like . Post poPetition 870170072933, of 28/09/2017, p. 12/59

9/48 may suitably contain from about 1 to about 10 weight percent of the compounds based on the total weight of the powder.

[0038] The formulations may additionally contain adjuvant surfactants to intensify the deposition, wetting and penetration of the compounds in the target crop or organism. These adjuvant surfactants can optionally be used as a component of the formulation or as a tank mixture. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 volume percent based on the volume of water spray, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to, ethoxylated nonyl phenols, ethoxylated natural or synthetic alcohols, salts of sulfosuccinic esters or acids, ethoxylated organosilicon, ethoxylated fatty amines, mixtures of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); ethoxylated nonylphenol; benzylcocoalkylldimethyl quaternary ammonium salt; mixture of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C ₉ - C ₁₁ alkyl _{polyglycoside} ; phosphate alcohol ethoxylate; natural primary alcohol ethoxylate (C ₁₂ - C ₁₆ ); block copolymer of di-secbutylphenol EO-PO; polysiloxane-methyl cap; ethoxylated nonylphenol + urea and ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); ethoxylated tallow amine (15 EO); dioleate-99 of PEG (400). The formulations may also include oil-in-water emulsions such as those disclosed in US Patent Application Serial No. 11 / 495,228, the description of which is expressly incorporated by reference in this document.

[0039] Formulations may optionally include combinations that contain other pesticidal compounds. These additional pesticidal compounds can be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactericides or combinations thereof

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10/48 that are compatible with the compounds of the present description in the medium selected for application, and not antagonistic to the activity of the present compounds. Consequently, in such embodiments, the other pesticidal compound is used as a supplementary toxic product for the same pesticide or for a different pesticide use. The compounds of Formula I and the pesticidal compound in the combination can generally be present in a weight ratio of 1: 100 to 100: 1.

[0040] The compounds of the present description can also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present description are generally applied in conjunction with one or more other fungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide (s), the compounds currently claimed can be formulated with the other fungicide (s), mixed in the tank with the other pesticide (s) or applied sequentially with the other pesticide (s). These other fungicides may include 2- (thiocyanatomethylthio) -benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulphate, ametoctradine, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus, benilx, subtilis, benzoxil, subtilis isopropyl, benzylaminobenzene sulphonate salt (BABS), bicarbonates, biphenyl, bismertiazole, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalide, bromuconazole, bupirimate, calcium polysulfide, captafolide, carbamide, captan, carbamino , carvone, clazafenone, chloroneb, chlorotalonyl, clozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), coumoxystrobin, cuprous oxide, ciazofamide, ciflufenamide, ciflufenamide, ciflufenamide, ciflufenamide, ciflufenamide Cyprodinila, dazomet, debacarb, ethylene oxis diamone Petition 870170072933, of 28/09/2017, p. 14/59

11/48 (dithiocarbamate), diclofluanide, dichlorophen, diclocimet, diclomezin, dichloran, dietofencarb, diphenoconazole, difenzoquat ion, diflumetorim, dimetomorph, dimoxystrobin, diniconazole, diniconazol-M, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton, dinobuton. dodemorph, dodine, dodine-free base, edifenfos, enestrobin, enestroburin, enoxastrobin, epoxiconazole, etaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, phenaminostrobin, fenarimol, phenbuconazole, phenoxamine, phenoxamine, phenoxamine, phenoxamine, , fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flufenoxystrobin, flumorfo, fluopicolide, fluopiram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianyl, flutolyl, fluoroethyl, fluoroethyl, fluoroethyl, fluoroethyl, fluorohydride -aluminum, fuberidazole, furalaxila, furametpir, guazatin, guazatin acetates, GY-81, hexachloroben zene, hexaconazole, himexazole, imazalil, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesylate), iodocarb, ipconazole, ipfenpirazolone, iprobenophilic, isopramide, isopramide, iprobamide, chloride, ipro hydrated casugamycin, cresoxim-methyl, laminarine, mancobre, mancozeb, mandestrobin, mandipropamide, maneb, mefenoxam, mepanipyrim, mepronila, meptil-dinocap, mercuric chloride, mercuric oxide, mercury chloride, metalaxyl, metalaxyl-M, methaxyl-M metam-potassium, metam-sodium, metconazole, metasulfocarb, methyl iodide, methyl isothiocyanate, metiam, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrotal-isopropyl, nuarimol, octilinone, ofuraceous, oleic acid (oleic acids) , oxadixyl, oxatiapiproline, oxin-copper, oxpoconazole fumarate, oxycarboxine, pefurazoate, penconazole, pencicuron, penflufen, pentachlorophenol, pentachloropheni l laurate, pentiopirad, phenylmercury acetate, phosphonic acid, phthalide, picarbutrazox, picoxystrobin, poPetition 870170072933, of 28/09/2017, p. 15/59

12/48 lioxin B, polyoxins, polyoxorin, potassium bicarbonate, hydroxyquinoline potassium sulphate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, protioconazole, pyraclostrobin, pyraclostrobin, pyretlostrobin, pyretlostrobin, pyretlostrobin, pyretlostrobin, pyretlostrobin, pyraclostrobin, pyraclostrobin, pyretlostrobin, pyretlostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyrethylobrazine. , pyributicarb, pyrifenox, pyrimethanil, pyrophenone, pyrisoxazole, piroquilone, quinoclamine, quinoxifene, quintozene, Reynoutria sachalinensis extract, silkxane, siltiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium bicarbonate, syringe Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, tifluzamide, thiophanate-methyl, remove, thiadinyl, tolclofos-methyl, tolprocarb, tolilfluanid, triadimefon, triadimide, triadimide, triadimide, triadimide triforin, triticonazole, validamycin, valifenalate, valifenal, vinclozolin, zineb, ziram, zoxa mida, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (RS) -N- (3,5dichlorophenyl) -2- (methoxymethyl) -succinimide, 1,2-dichloropropane, 1, Hydrated 3dichloro-1,1,3,3-tetrafluoroacetone, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 1,1,4,4-tetraoxide 2- (2heptadecyl-2-imidazolin-1- il) ethanol, 2,3-dihydro-5-phenyl-1,4-dithine, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3- (4-chlorophenyl) -5- methylrodanine, 4- (2-nitroprop-1enyl) phenyl thiocyanate, ampropylphos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacrila; benzamacryl-isobutyl, benzamorf, binapacryl, bis (methylmercury) sulfate, bis (tributyltin) oxide, butiobate, calcium copper and zinc cadmium chromate sulfate, carbamorph, ECSC, clobentiazone, chloramphoromethane, chlorfenazole, chlorine, bis Copper phenylsalicylate), copper and zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, ciclafuramid, cipendazole, ciprofuram,

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13/48 decafentin, diclone, diclozoline, diclobutrazol, dimethyrimol, dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimphos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, phenaminosulf, fenapanil, furapanil, furanzol, furanzol, furanzol, furanzol, furanzol, furanzol, furanzolan, -cis, furmeciclox, furofanato, gliodina, griseofulvina, halacrinato, Hercules 3944, hexiltiofos, ICIA0858, isopamfos, isovaledione, mebenila, mecarbinzide, metazoxolon, metfuroxam, methylmercury-dichloromethane, methoxy-hydroxy-methoxy-hydroxy, methoxy-hydroxide, methoxy-hydroxy-hydroxy-hydroxy-hydroxy, hydroxy dichlorophenylsuccinimide, W-3-nitrophenylitaconimide, natamycin, W-ethylmercury-4toluenesulfonanilide, nickel bis (dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, protocarbene; protiocarb hydrochloride, piracarbolid, pyridinitrile, pyroxychlor, pyroxifur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropene, weave, thiadifluoride, thiocyanin, thioclorphenphen, thiophanate, thioquinox, thioximide, triamiphos, triarimol, triazide, triazide, triazide, triazide, tridazide

[0041] Additionally, the compounds described in this document can be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the compounds of the present description in the medium selected for application, and not antagonistic to activity of the present compounds to form mixtures of pesticides and synergistic mixtures thereof. The fungicidal compounds of the present description can be applied in conjunction with one or more other pesticides to control a wider range of undesirable pests. When used in conjunction with other pesticides, the compounds currently claimed can be formulated with other pesticide (s), mixed in tank with other pesticide (s) or applied sequentially with other pesticide (s). Typical insecticides

Petition 870170072933, of September 28, 2017, p. 17/59

14/48 include, but are not limited to: 1,2-dichloropropane, abamectin, acephate, acetamiprid, acetion, acetoprol, acrinatrine, acrylonitrile, aphidopyropene, alanicarb, aldicarb, aldoxicarb, aldrin, aletrine, alosamidine, alpha-ketamine, alpha-ketamine ecdysone, alpha-endosulfan, amidition, aminocarb, amiton, amiton oxalate, amitraz, anabasine, atidation, azadiraquitine, azametiphos, azinphos-ethyl, azinphos-methyl, nitrogen, barium hexafluorosilicate, bartrine, bendocarb, bendiocarb, bendiocarb beta-cypermethrin, bifenthrin, bioalethrin, bioethanometrine, biopermethrin, bistrifluron, borax, boric acid, broflanilide, bromphenvinfos, bromocyclen, bromo-DDT, bromophos, bromofos-ethyl, bufencarb, buprofezin, butprophar , calcium arsenate, calcium polysulfide, canfeclor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbofenotion, carbosulfan, cartap, cartap hydrochloride, c lorantraniliprol, clorbiciclen, chlordane, chlordecone, chlordimeform, chlordimeform hydrochloride, chlorethoxyphos, chlorfenapyr, chlorfenvinfos, chlorfluazuron, clormefos, chloroform, chloropicrin, chlorfoxin, chlorprinoform, chloropyrine, chlorpyrine, chlorpyrine, chlorpyrine cyismetrine, claciphos, cloetocarb, closantel, clothianidin, copper acetoarsenia, copper arsenate, copper naphthenate, copper oleate, coumafos, coumitoate, crotamiton, crotoxifos, crufomato, cryolite, cyanofenphos, cyanofanthyl, cyanophilol, cyanophylline, cyanophilol, cyanophylline cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, cytomate, DDT, decarbofuran, deltamethrin, demefion, demefion-O, demefion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-O-methyl, demeton-O-methyl, demeton-O-methyl, demeton-S-methyl, demeton-S-methylsulfon, diafentiuron, dialiphos, diatomaceous earth, diazinon, dicapton, diclofention, dichlorvos, dichloromezothiaz, dicresila, dicrotofos, dicic lanila, dieldrin, diflubenzuron, dilor, dimeflutrina, dimefox, dimetan, dimetoato, dimetrina, dimethilvinfos, dimethilan, dinex, dinex-diclexina, dinoprop, diPetição 870170072933, of 28/09/2017, p. 18/59

15/48 nosam, dinotefuran, diophenolan, dioxabenzofos, dioxacarb, dioxation, disulfoton, dithrophos, d-limonene, DNOC, DNOC-ammonium, DNOCpotassium, DNOC-sodium, doramectin, ecdysterone, emamectin, emamectin benzoate, EMPC, EMPC, EMPC , endothionin, endrine, EPN, epophenonane, eprinomectin, sdepalethrin, sphenopherate, etafos, etiofencarb, etion, etiprol, ethoate-methyl, etoprofos, ethyl formate, ethyl-DDD, ethylene dichromide, ethylene dioxide, ethylene dioxide, ethylene oxide , etrimfos, EXD, famfur, fenamifos, fenazaflor, fenclorfos, fenetacarb, fenflutrina, fenitrotion, fenobucarb, fenoxacrim, fenoxicarb, fenpiritrina, fenpropatrina, fensulfotion, fention, fention-ethyl, fenvalerato, flonofon, flemofon, flendon, flemofon, flomofon, flomquide , flucitrinate, flufenerin, flufenoxuron, flufenprox, flufiprol, fluhexafon, flupiradifurone, fluvalinate, fonofos, formetanato, formetanato hydrochloride, formotion, formparanate, formparanate hydrochloride, fo smethylane, phospirate, fostietane, furatiocarb, furetrina, gamacihalotrina, gama-HCH, halfenprox, halofenozida, HCH, HEOD, heptachlor, heptaflutrin, heptenofos, heterofos, hexaflumuron, HHDN, hydramethilrina, imidio, hydroxy, hydrochloride, hydrochloride, hydroxy indoxacarb, iodomethane, IPSP, isazofos, isobenzan, isocarbofos, isodrine, isofenphos, isofenfos-methyl, isoprocarb, isoprothiolane, isothioate, isoxation, ivermectin, jasmine I, jasmine II, jodfenfos, juvenile hormone, juvenile hormone kappabifentrin, kappa-teflutrin, quelevan, quinoprene, lambda-cyhalothrin, lead arsenate, lepimectin, leptophos, lindane, lirimphos, lufenuron, litidation, malation, malonoben, mazidox, mecarbam, mesarfon, mesarfon, metarfon, metarfon, metarfos, metarfos , methacrifos, metamidophos, metidation, metiocarb, metocrotofos, metomila, methoprene, methoxychloride, methoxyfenozide, methyl bromide, methyl isothiocyanate, methylchloroform, c methylene chloride, metoflutrin, metolcarb, methoxyzone, mevinfos, mexacarbato, milbemectin, milbemiPetition 870170072933, of 28/09/2017, p. 19/59

16/48 cina oxime, mipafox, mirex, molosultap, monfluorothrin, monocrotophos, monomehipo, monosultap, morfotion, moxidectin, naphthalophos, nalede, naphthalene, nicotine, nifluridide, nitenpiram, nitiazine, oxide, novilate, nitrilaconb, novilone methyl, oxideprofos, oxydisulfoton, para-dichlorobenzene, paration, paration-methyl, penfluron, pentachlorophenol, permethrin, fencapton, phenothrin, phentoate, forato, phosalone, phospholane, fosmet, fosniclor, fosfamidon, phosphine, foximim, pirximet pyrimiphos-ethyl, pyrimiphos-methyl, potassium arsenate, potassium thiocyanate, pp'-DDT, pralethrin, precocene I, precocene II, precocene III, primidofos, profenofos, profluralin, promacila, promecarb, propafos, propetamfos, propetamfos, propuramos protiofos, protoato, protrifenbute, piflubumide, piraclofos, pirafluprol, pyrazophos, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins, pyridaben, pyridalil, pyridafention, pyrifluquinazon, pyrimidifene, pyrimidine iminostrobin, pyrimitate, pyriprol, pyriproxifene, quassia, quinalfos, quinalfos-methyl, quinotion, rafoxanide, resmetrine, rotenone, riania, sabadila, scradan, selamectin, silafluofen, silica gel, sodium arsenate, fluoride, sodium fluoride, fluoride sodium thiocyanate, sofamide, spinetoram, spinosad, spiromesifeno, spirotetramat, sulcofurone, sulcofurone-sodium, sulfluramide, sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, taufluvalinate, tazimcarb, TDE, tebufeno-tefephine, tebufen, tebufen, tebufen TEPP, teralethrin, terbufos, tetrachloroethane, tetrachlorvinfos, tetramethrin, tetramethylflutrin, tetraniliprol, theta-cypermethrin, thiacloprid, thiamethoxy, tetrahydrate, tiocrophosphate, tiocrophosphate, tiocrophosphate, thiocarbonate, thiocarbonate, thiocarbonate thuringiensin, thioxazafene, tolfenpirade, tralometrine, transflutrin, transpermethrin, triaratene, triazamate, triazophos, trichlorfon, triclormetafos-3, tricloronat, triphenofos, triflumezopirim, triflumuron, trimetacarb, tripreno, vamidotion, vaniliprol, XMC, xylilcarb, zeta-cypermethrin, zolaprofos, and any combinations

Petition 870170072933, of September 28, 2017, p. 20/59

17/48 of them.

[0042] Additionally, the compounds described in this document can be combined with herbicides that are compatible with the compounds of the present description in the medium selected for application, and not antagonistic to the activity of the present compounds to form mixtures of pesticides and synergistic mixtures thereof. The fungicidal compounds of the present description can be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants. When used in conjunction with herbicides, the compounds currently claimed can be formulated with the herbicide (s), mixed in tank with the herbicide (s) or applied sequentially with the herbicide (s). Typical herbicides include, but are not limited to: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4DEB, 2,4 -DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, alachlor, alidochlor, aloxidim, alorac, ametridione, ametrin , amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralide, amiprofos-methyl, amitrol, ammonium sulfamate, anilophos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotine, benflamine, benflam, benzoin , bensulfuron-methyl, bensulide, bentiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoilprop, benztiazuron, bialafos, bicyclopyrone, biphenox, bilanafos, bispyrobromine, byribromine, byribromine, byribromine, bromobromine, bromibromine, bromibromine , bromoxynil, brompirazon, butachlor, butafenacil, butamiphos, butenachlor, butidazole, butiuron, butralin, butroxidim, buturon, butylate, cacodylic acid, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chloramben, chloranocrila, chlorazifop, chlorazin, chlorbromuron, chlorobur, chlorochloride, chlorhexyl, chlorhexyl, chloramide , of 28/09/2017, p. 21/59

18/48 rimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorprofam, chlorsulfuron, clortal, chlortiamid, cinidon-ethyl, cinmetilin, cinosulfuron, cisanilide, cletodim, cliodinate, clodinafopopropone, clodinopopopropyl, clodinopopoprom, propyl , chloransulammethyl, CMA, copper sulphate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrin, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxidim, cycluron, cihalofop-butyl, cyperquat, cyprazine, cyprazole, cyprazole, cyprazole, cyprazole, cyprazole, cyprazole, cyprazole , desmedifam, desmetrin, di-alate, dicamba, dichlobenyl, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, diethyl, difenopenten, difenoxuron, difenzoquat, dimetufet, diflufen, dimlufen, dimlufen, dimlufen , dimetenamide-P, dimexane, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, disul, dithiopir, diuron, DMPA, DNOC, DSMA, EBEP, eg linazine, endotal, epronaz, EPTC, erbon, esprocarb, etalfluralin, etametsulfuron, etidimuron, etiolate, etofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromide, etobenzanide, EXD, fenasulam, phenoxy, phenoxyphenone, phenoxyphenone, phenoxyphenone fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flampropM, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, flucloralin, flufenacet, flufenican, flufen, flufen, flufen, flumezum , fluoroglycofen, fluoromidine, fluoronitrophen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, flutiacet, fomesafen, foramsulfuron, phosphorus, glufin, halofin, glufin, flufox , haloxidine, haloxifop, haloxifop-P, hexachloroacetone, hexaflurate, hexazinone, imazametabenz, imazamox, imaz apic, imazapyr, imazaquin, imazetapyr, imazosulfuron, indanofan, indaziflam, iodobonyl, iodomethane, iodosulfuron, iofensulfuron, ioxynil,

Petition 870170072933, of September 28, 2017, p. 22/59

19/48 ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isometiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxaclortol, isoxaflutol, isoxapirifop, MC, PA, linoxac, PA -thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, metabenztiazuron, metpropalin, metpropalin, metpropalin, metpropalin, metpropalin, metpropalin , methyl bromide, methyl isothiocyanate, methyldimron, metobenzuron, metobromuron, metolachlor, metosulam, methoxyuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, nafampropam, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orthodichlorobenzene, ortosulfamuron, orizalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxazyclomone, oxifluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimetalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, phenofenamide, phenoxyphenol, phenoxymethyl, phenoxyphenol, phenoxyphenol, phenoxyphenol , picolinafen, pinoxaden, piperophos, potassium arsenate, potassium azide, potassium cyanide, pretilachlor, primisulfuron-methyl, prociazine, prodiamine, profluazole, profluralin, profoxidim, proglinazine, prometon, propetrin, propaquizine, propaquizine, propaquizine, propachlor, propachlor, propachlor, propaquizine , propisochlor, propoxycarbazone, propyrisulfuron, propizamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prinaclor, pidanon, piraclonila, piraflufen, pirasulfotol, pyrazolinate, pirazosulfuron, pyrazoxifen, pyribenzoxim, pyridine, pyributyride, pyributyride, pyributyride, pyributicarb , pyroxsulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P, rhodetanil, rimsulfuron, saflufenacil, S-metolachlor, sebutilazine,

Petition 870170072933, of September 28, 2017, p. 23/59

20/48 secbumeton, setoxidim, siduron, simazine, simeton, simetrin, SMA, sodium arsenate, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid, sulglicapin, swep, TCA, tebutam, tebutiuron, tefuriltrione, tembotrione, tepraloxidim, terbacil, terbucarb, terbuclor, terbumeton, terbutilazine, terbutrin, tetrafluron, tenilchlor, thiazafluron, tiazopir, tidiazimin, tidiazuron, tenciazuron, tenciabyron, tenciabone, tencarbazone tralcoxidim, triafamone, tri-alate, triasulfuron, triaziflam, tribenuron, tricamba, triclopir, tridifano, trietazine, trifloxisulfuron, trifludimoxazin, trifluralin, triflusulfuron, trifop, trifoptrin, trifops, trifoxy, trifoxy, trifoxy, triloxy

[0043] Another modality of the present description is a method of controlling or preventing an attack by fungi. This method includes application to the soil, plant, roots, foliage, or the location of the fungus, or to a location where infestation is to be prevented (for example, application to cereals or vines), a fungally effective amount of one or more of the compounds of Formula I. The compounds are suitable for the treatment of several plants at the fungicidal level, while having low phytotoxicity. The compounds can be useful both in a protective and / or eradicating manner.

[0044] The compounds were found to have a significant fungicidal effect on for agricultural use. Many compounds are particularly effective for use with agricultural crops and horticultural plants. [0045] It will be understood by those skilled in the art that the effectiveness of the compound for the previously exposed fungi establishes the general utility of the compounds as fungicides.

[0046] The compounds have broad ranges of activity against fungal pathogens. Exemplary pathogens may include, but are not

Petition 870170072933, of September 28, 2017, p. 24/59

21/48 limited to, causative agent of Wheat Leaf Stain (Zymoseptoria tritici), Brown Wheat Rust (Puccinia triticina), Striated Wheat Rust (Puccinia striiformis), Apple Scab (Venturia inaequalis), Vine Oidium (Uncinula necator) ), Barley Scald (Rhynchosporium secalis), Rice Blast (Pyricularia oryzae), Soybean Rust (Phakopsora pachyrhizi), Wheat Glaze (Leptosphaeria nodorum), Wheat Powder (Blumeria graminis f. Sp. Tritici), Barley (Blumeria graminis f. sp. hordei), Powdery mildew (Erysiphe cichoracearum), Cucurbit anthracnose (Glomerella lagenarium), Beet leaf spot (Cercospora beticola), Pinta Preta do Tomate (Alternaria solani) and (Cochliobolus sativus). The exact amount of active material to be applied depends not only on the specific active material being applied, but also on the specific action desired, the species of fungi to be controlled and the stage of their growth, as well as the part of the plant or of another product that should come into contact with the compound. Thus, all compounds and formulations containing the same, may not be equally effective at similar concentrations or against the same species of fungi. [0047] The compounds are effective in use with plants in a disease-inhibiting and phytologically acceptable amount. The term disease-inhibiting and phytologically acceptable amount refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but which is not significantly toxic to the plant. This amount will generally be about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of the required compound varies with the fungal disease to be controlled, the type of formulation used, the method of application, the specific plant species, the climatic conditions and the like. An appropriate application fee

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22/48 typically ranges from about 0.01 to 0.45 grams per square meter, g / m ² (about 0.10 to about 4 pounds / acre).

[0048] Any desired range or value mentioned in this document can be extended or changed without losing the intended effects, as is evident to those skilled in the art to understand the teachings contained in this document.

[0049] The compounds of Formula I can be made using well-known chemical procedures. Intermediates not specifically mentioned in this description are commercially available, can be made by the routes disclosed in the chemical literature, or can be easily synthesized from commercial raw materials, using standard procedures.

GENERAL SCHEMES [0050] The following scheme illustrates an approach to generate Formula I picolinamide N-oxide compounds. The following description and example are provided for illustrative purposes and should not be construed as limiting in terms of substituents or substitution patterns .

[0051] The compounds of Formula I, in which R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₈ are as originally defined, can be prepared according to the method outlined in Scheme 1, step a. The compounds of Formula 1.0, where R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₈ are as originally defined, can be prepared as described by the procedures outlined in US patent applications WO WO 2016/109289, WO 2016 / 109257, WO 2016/109302 and WO 2016/109304. The Formula 1.0 compounds can be treated with a diativated carbonyl reagent, such as triphosgene, with a base, such as pyridine, in a polar solvent, such as dichloromethane (CH2Cl2), at a temperature of about 0 ° C to 50 ° C ° C to generate the compounds of Formula I, where R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₈ are as originally defined, as

Petition 870170072933, of September 28, 2017, p. 26/59

23/48 shown in a.

EXAMPLES

[0052] Example 1: Preparation of (S) -1,1-di-p-tolylpropan-2-yl- (S) 2- (8-methoxy-2,4-dioxo-2H-pyrido [2,3- and] [1,3] oxazin-3 (4H) -yl) propanoate.

[0053] To a solution of (S) -1,1-di-p-tolylpropan-2-yl (3-hydroxy-4-methoxypolycolinoyl) -L-alaninate (WO 2016/109257) (0.035 g, 0.076 mmol ) and triphosgene (0.045 g, 0.151 mmol) in CH ₂ Cl ₂ (0.76 mL) was added pyridine (0.122 mL, 1.513 mmol). The reaction was stirred at room temperature until complete consumption of the raw material was observed by TLC (50% acetone in hexanes). The reaction mixture was stopped with saturated NaHCO3 (10 ml), extracted with CH2Cl2 using a phase separator, and concentrated under reduced pressure. The crude residue was purified by automated silica gel chromatography (0-50% acetone in hexanes) to provide (S) -1,1di-p-tolylpropan-2-yl- (S) -2- (8-methoxy -2,4-dioxo-2H-pyrido [2,3e] [1,3] oxazin-3 (4H) -yl) propanoate (23.8 mg, 0.046 mmol, 61.2% yield) as a thick oil . ¹ H NMR (500 MHz, CDCl ₃ ) δ 14.31 (s, 1H), 12.64 (d, J = 7.0 Hz, 1H), 7.85 (d, J = 7.2 Hz, 1H ), 7.17

Petition 870170072933, of September 28, 2017, p. 27/59

24/48 (d, J = 7.9 Hz, 1H), 7.11 (d, J = 7.7 Hz, 1H), 6.98 - 6.88 (m, 3H), 6.80 (s , 1H), 6.75 (d, J = 7.1 Hz, 1H), 5.67 (dq, J = 10.2, 6.1 Hz, 1H), 4.52 4.38 (m, 2H ), 3.96 (s, 3H), 2.35 (s, 3H), 2.28 (s, 3H), 2.24 (s, 3H), 2.20 (s, 3H), 1.30 (d, J = 6.2 Hz, 3H), 1.11 (d, J = 7.2 Hz, 3H). IR (thin film) 2934, 1736, 1644, 1569, 1533, 1480, 1454, 1301, 1207, 1155, 1030, 911.808, 733 cm ^-1 . ESIMS m / z 507.2 ([M + H] +).

[0054] The structures and appearance of the compounds and methods of preparing the compound of the present description are shown below in Table 1. The analytical data for the compounds shown in Table 1 are shown below in Table 2.

Example A: Fungicidal Activity Evaluation: Wheat leaf spot (Zymoseptoria tritici; Bayer SEPTTR code):

[0055] The technical grades of the materials were dissolved in acetone, and were then mixed with nine volumes of water (H ₂ O) containing 110 ppm of Triton X-100. The fungicide solutions were applied to wheat seedlings using a cabin spray to cover superficially. All sprayed plants were allowed to dry in the open air for later handling. All fungicides were evaluated using the method mentioned above for their activity vs. all target diseases, unless otherwise specified. The activity of leaf spot and brown rust of wheat were also evaluated using spray applications in trails, in which case the fungicides were formulated as EC formulations, containing 0.1% Trycol 5941 in the spray solutions.

[0056] Wheat plants (variety Yuma) were grown from seeds in a greenhouse in a Metro mixture 50% mineral soil / 50% without soil until the first leaf emerged completely, with 7-10 seedlings per pot. These plants were inoculated with an aqueous spore suspension of Zymoseptoria tritici before or after fungicide treatments. After inoculation, the plants were maintained 870170072933, from 28/09/2017, p. 28/59

25/48 at 100% relative humidity (one day in a dark dew chamber followed by two to three days in a dew chamber lit at 20 ° C) to allow the spores to germinate and infect the leaf. The plants were then transferred to a greenhouse at 20 ° C for the disease to develop. When the symptoms of the disease were fully expressed in the 1 ^to leaves of untreated plants, the levels of infection were assessed on a scale of 0 to 100 percent severity of the disease. The percentage of disease control was calculated using the ratio of disease severity in treated plants to untreated plants. The results of the evaluations are shown below in Table 4.

Example B: Fungicidal Activity Evaluation: Brown wheat rust (Puccinia triticina; synonym: Puccinia recondita f. Sp. Tritici; Bayer PUCCRT code):

[0057] Wheat plants (variety Yuma) were grown from seeds in a greenhouse in a Metro mixture 50% mineral soil / 50% without soil until the first leaf emerged completely, with 7-10 seedlings per pot. These plants were inoculated with an aqueous spore suspension of Puccinia trithycin before or after fungicide treatments. After inoculation, the plants were kept in a dark dew environment at 22 ° C with 100% relative humidity overnight to allow the spores to germinate and infect the leaf. The plants were then transferred to a greenhouse at 24 ° C for the disease to develop e. Fungicide formulation, application and disease evaluation followed by the procedures as described in Example A. The results of the evaluations are shown below in Table 4.

Example C: Fungicidal Activity Assessment: Asian soybean rust (Phakopsora pachyrhizi; Bayer PHAKPA code):

[0058] The technical grades of the materials were dissolved in accordance with 870170072933, of 28/09/2017, p. 29/59

26/48 surface, and were then mixed with nine volumes of water H ₂ O containing 0.011% Tween 20. The fungicide solutions were applied to soybean seedlings using a cabin spray to cover superficially. All sprayed plants were allowed to dry in the open air for later handling.

[0059] The soybean plants (Williams 82 variety) were grown in a Metro mix without soil, with one plant per pot. Two-week seedlings were used for testing. The plants were inoculated 3 days before or 1 day after fungicide treatments. The plants were incubated for 24 hours in a dark environment with dew at 22 ° C and 100% relative humidity, and then transferred to a growth environment at 23 ° C for the disease to develop. The severity of the disease was assessed in the sprayed leaves. The results of the assessments are shown below in Table 5.

Table 1. Compound Structure, Preparation Method and Appearance

Compound n ° Structure Prepared from a deal with Appearance 1 THE ° ° 0 | H ’ n y ^ y o y ^ o CH3 F WO 2016/109257 Example 1 Solid White 2 H ₃ C _X o \ H ° ^CH3 \ H Ao A ^ / AA n AA A o o ^{cf |} 3 F WO 2016/109257 Example 1 Pale yellow oil

Petition 870170072933, of September 28, 2017, p. 30/59

27/48

Compound n ° Structure Prepared from a deal with Appearance 3 H ₃ C _x 0 Αχ ° χ ° o ^H3C and ^CH3 π ^Ν Λ ° 0 ch ₃ ch ₃ XX WO 2016/109302 Example 1 Yellow oil 4 ^H 3 ^C .q Χχ x ° x / O r ιΧ i ° ^CH3 XX ^o ϊ'Υ ⁵ ] O CH ₃ XX h ₃ c ch ₃ ch ₃ ³ WO 2016/109289 Example 1 Pale yellow oil 5 HsC.q X ^ X ° X ° ° ^{CH3 k} X ^N X ° X ° iu ° ^CH3 XX, ch ₃ ch ₃ WO 2016/109289 Example 1 Colorless, clear oil 6 WX ° XX ^ O ch ₃ ch ₃ WO 2016/109302 Example 1 Pale yellow oil 7 h ₃ c _x O ch ₃ ÒXXx r XT N · <O> · ° xx F WO 2016/109257 Example 1 Pale yellow oil 8 H3C O Xif ° Y ° 0 CH XY% h ₃ X XX Χχ, χΧΧ n · <ο O CH ^ XJ \ o _x -3 '^ J CH3 o _x CH3 WO 2016/109257 Example 1 Colorless, clear oil

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Compound n ° Structure Prepared from a deal with Appearance 9 ^h 3 _{C. o} γ ¥ -Χ'ηΧ o ch ₃ Υχγτ ch ₃ ch ₃ WO 2016/109289 Example 1 Pale yellow oil 10 X YX X o ch ₃ ch ₃ iiY O ch ₃ L ¥ x ch ₃ WO 2016/109289 Example 1 Pale yellow oil 11 ^H X ôCÇi r, G ^F n YY γ ο Y · o CH ₃ J \ .CH ₃ kk F WO 2016/109257 Example 1 Pale yellow oil 12 ^H X o ch ₃ XYY ^F % 4γ ^Ν γό _ο ΛΥΥ O ^CH3 kj F WO 2016/109257 Example 1 Pale yellow oil 13 ch ₃ ^H 3 ^C Y k / OJ XY S 1 Xt ° t ° Y o ch ₃ ch ₃ ¥ k WO 2016/109302 Example 1 Orange oil 14 ^H3 % f Q _CH , ZZ \ n YY · <ο X ° ^CH3 XY F ^ XX WO 2016/109257 Example 1 Orange oil

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Compound n ° Structure Prepared from a deal with Appearance 15 H ₃ C _x o or ° Y ° jp if ^N, T ° l ° Yb o ch ₃ F WO 2016/109304 Example 1 Orange oil 16 ^H 3 <U _o Js. κ ir ro CH ₃ ci% VA O ch ₃ AY ^ Y ch ₃ ch ₃ WO 2016/109289 Example 1 Orange oil 17 H ₃ C. O ° ^CH 3 Y ^ Yl ζ II. λ A.II N γ O> ·· ^CH 3 II ch ₃ WO 2016/109257 Example 1 Orange oil 18 ^H 3 _% γ Ip o ch ₃ γ by ch ₃ k JL / ¼ J n NU γ o ^ Y ° ^CH3 ° όη ₃ WO 2016/109257 Example 1 Solid brown 19 ^H 3 _% άγνυγ O ch ₃ ch ₃ II F WO 2016/109257 Example 1 Orange oil

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Compound n ° Structure Prepared from a deal with Appearance 20 Άχχ 'o ch ₃ À .o, CH3 F WO 2016/109257 Example 1 Orange oil 21 ^H 3 _% κ rr ro ch ₃ ci kV / Ã-vA ^{0 CH} 3 WO 2016/109304 Example 1 Orange oil 22 H₃ç_x the ch₃ ^ O, / O, F °^ch3 rn ^ k II X 1, U N XX y Ο η · the CH₃ V N WO 2016/109257 Example 1 Orange oil 23 ^H 3 _% ^ γ ^Ο γ ° _O ^H 3 ^C \ / ^CH 3 ^ γ ^Ν '' · '^ ^ο> γ ^ο γ ^ O ch ₃ ch ₃ I / CH ₃ o WO 2016/109302 Example 1 Orange oil 24 ^H3C -O fXX ⁰ ^ ⁰ ° ^CH 3 ° ^CHs H _S C - \ „II WO 2016/109289 Example 1 Orange oil 25 ^H 3 _% ✓xx / O \, χ-O ^ ΟΗβ οαΐΑΐΧΐ n XX yoy O CH ₃ ^F yX \ ch ₃ WO 2016/109257 Example 1 Thick oil

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Compound n ° Structure Prepared from a deal with Appearance THE frog ° to ° CH3 AA x-Cl WO N \ A/ Oil es- 26 2016/109257 Ch ₃ .0 A 0, Example 1 people H3C \ il CH3 OK Cl h ₃ A O iAA _z o. A T 5 ch ₃ A YY ^CI WO \ TA N x < ^N '-T ^ o THE Oil es- 27 π 1 2016/109257 0 ch ₃ Example 1 people Aa THE Cl H ₃ A O F I V ^F AA .O. /O T1 ch ₃ A THE WO Oil es- 28 N γ ^Ν -Λ ₀ THE 2016/109257 íí Γ Example 1 people 0 ch ₃ 1 AA Aa H ₃ A O rfA T J ch ₃ A F WO \ <A \ N Α ·· ΑΑ ζγ A / Oil es- 29 T Γ 2016/109257 The ch ₃ AA Example 1 people aa f h ₃ A O h ₃ c _Z CH, WO Oil ffA A ° es- 30 _Y A ° - 2016/109302 N THE THE Example 1 people 0 ch ₃ ch ₃ L ΆΑ ch ₃ THE , <Y / O WO Oil iA A ^ 0 N already CH3 es- 31 1 2016/109289 N T i ^ o TT T Example 1 people 0 ch.-h.-c ,. THE.,, xA \ CH3

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Compound n ° Structure Prepared from a deal with Appearance 32 H ₃ C _x 0 Á. W .0 / CH ₃ fi T s ϊ ^Η · Hf ^{0 CHs} ch ₃ WO 2016/109257 Example 1 Thick oil 33 ^Η 3 <γ Ãí ./. Çr 'O ch ₃ A. ch ₃ ch ₃ WO 2016/109257 Example 1 Thick oil 34 ^H 3 _% / Ά ^Ο Ά ° ₀ ç _H3 k ÁÁs / n YY γ ο γ 0 ch ₃ rn Ak F WO 2016/109257 Example 1 Thick oil 35 HsA 0 ch ₃ Va k ^<N Af A ° i Ά O ch ₃ ch ₃ kk WO 2016/109302 Example 1 Thick oil

* Compound # - compound number

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Table 2. Analytical data

Compound n ° Point of melting (° C) IR (cm ^-1 ) Spectrometry Pasta NMR 1 68-84 ESIMS m / z 497.1 ([M + H] +) ¹ H NMR (400 MHz, CDCfe) δ 8.61 (d, J = 5.3 Hz, 1H), 7.19 - 7.03 (m, 5H), 7.01 - 6.88 (m, 2H ), 6.88 - 6.74 (m, 2H), 5.74 - 5.59 (m, 1H), 5.42 (q, J = 7.1 Hz, 1H), 4.06 (s, 3H), 3.98 (d, J = 7.2 Hz, 1H), 1.53 (d, J = 7.1 Hz, 3H), 1.20 (d, J = 6.2 Hz, 3H) . ¹³ C NMR (101 MHz, CDCfe) δ 168.0, 161.7 (d, J = 245.8 Hz), 161.4 (d, J = 245.2 Hz), 158.6, 154.2, 149, 1, 145.7, 141.6, 136.8 (d, J = 3.2 Hz), 136.2 (d, J = 3.1 Hz), 131.4, 130.1 (d, J = 8.0 Hz), 129.7 (d, J = 7.9 Hz), 115.5 (d, J = 21.3 Hz), 115.3 (d, J = 21.3 Hz), 111.3, 73.5, 56.8, 54.9, 51.3, 18.6, 13.9. 2 IR (thin film) 2946, 1770, 1713, 1603, 1501, 1371, 1081, 966, 909, 850, 729 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C26H20F 4N2NaO6, 555.1150; found, 555.1150 ¹ H NMR (400 MHz, CDCh) δ 8.61 (d, J = 5.3 Hz, 1 H), 7.26 - 7.09 (m, 3H), 6.90 - 6.81 (m, 1H), 6.81 - 6.62 (m, 3H), 5.71 - 5.60 (m, 1H), 5.41 (q, J = 7.0 Hz, 1H), 4.60 (d , J = 8.5 Hz, 1H), 4.07 (s, 3H), 1.65 - 1.52 (m, 3H), 1.29 - 1.18 (m, 3H). ¹⁹ F NMR (376 MHz, CDCh) δ 111.16 (d, J = 7.6 Hz), -111.77 (d, J = 7.5 Hz), -111.96 (dd, J = 7, 5, 1.9 Hz), -112.77 (dd, J = 7.9, 2.0 Hz).

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3 IR (thin film) 2966, 1715, 1600, 1501, 1371, 1242, 1080, 749 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C23H26N2NaO7, 465.1632; found, 465.1618 ¹ H NMR (400 MHz, CDCh) δ 8.60 (d, J = 5.3 Hz, 1H), 7.31 - 7.21 (m, 2H), 7.13 (d, J = 5.3 Hz, 1H), 6.93 (td, J = 7.4, 1.1 Hz, 1H), 6.91 - 6.86 (m, 2H), 5.70 (q, J = 7.0 Hz , 1H), 5.07 (dd, J = 6.7, 4.6 Hz, 1H), 4.47 (p, J = 6.2 Hz, 1H), 4.05 (s, 3H), 2 , 12 (pd, J = 6.9, 4.7 Hz, 1H), 1.75 (d, J = 7.1 Hz, 3H), 1.30 (d, J = 6.2 Hz, 3H) , 0.95 (d, J = 6.9 Hz, 3H), 0.85 (d, J = 6.8 Hz, 3H). ¹³ C NMR (101 MHz, CDCfe) δ 168.33, 158.78, 157.42, 154.20, 149.11, 145.83, 141.67, 131.53, 129.53, 121.05, 115, 92, 111.32, 81.11, 72.59, 56.79, 51.61, 28.61, 19.36, 16.89, 15.88, 14.22. 4 IR (thin film) 2956, 1769, 1713, 1600, 1501, 1371, 1241, 1082, 749 cm ^-1 HRMS-ESI (m / z) [M + H] + calculated for C24H29N2O7, 457.1969; found, 457.1965 ¹ H NMR (400 MHz, CDCfe) δ 8.58 (d, J = 5.3 Hz, 1H), 7.09 (d, J = 5.3 Hz, 1H), 7.04 - 6.97 ( m, 2H), 6.90 - 6.84 (m, 2H), 6.61 (tt, J = 7.2, 1.1 Hz, 1H), 5.50 (q, J = 7.0 Hz , 1H), 5.37 (qd, J = 6.4, 1.9 Hz, 1H), 4.14 (d, J = 1.9 Hz, 1H), 4.04 (s, 3H), 1 , 59 (d, J = 7.1 Hz, 3H), 1.29 (d, J = 6.4 Hz, 3H), 1.01 (s, 9H). ¹³ C NMR (126 MHz, CDCh) δ 167.89, 159.91, 158.51, 154.12, 148.91, 145.70, 141.53, 131.37, 129.03, 120.14, 115.42, 111.14, 85.86, 73.95, 56.73, 51.49, 35.37, 26.77, 15.49, 13.94.

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5 IR (thin film) 2964, 1768, 1711, 1488, 1371, 1240, 1082, 728 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C25H29ClN2NaO7, 527,1556; found, 527.1553 ¹ H NMR (400 MHz, CDCb) δ 8.58 (d, J = 5.3 Hz, 1H), 7.09 (d, J = 5.3 Hz, 1H), 7.00 - 6.91 ( m, 2H), 6.78 - 6.69 (m, 2H), 5.50 (q, J = 7.0 Hz, 1H), 5.21 (qd, J = 6.3, 2.7 Hz , 1H), 4.28 (dd, J = 8.2, 2.7 Hz, 1H), 4.03 (s, 3H), 1.57 (d, J = 7.0 Hz, 3H), 1 , 55 - 1.39 (m, 2H), 1.39 - 1.24 (m, 6H), 0.87 (t, J = 7.4 Hz, 3H), 0.77 (t, J = 7 , 4 Hz, 3H). ¹³ C NMR (126 MHz, CDCb) δ 168.20, 158.50, 158.29, 153.95, 149.06, 145.69, 141.31, 131.16, 128.98, 124.89, 116.38, 111.21, 80.59, 73.98, 56.72, 51.39, 42.27, 21.08, 20.84, 13.99, 13.35, 10.57, 10, 24. 6 IR (thin film) 2941, 1768, 1711, 1599, 1501, 1370, 1240, 1079, 733, 728 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C22H24N2NaO7, 451.1476; found, 451.1468 ¹ H NMR (400 MHz, CDCb) δ 8.59 (d, J = 5.3 Hz, 1H), 7.30 - 7.19 (m, 2H), 7.12 (d, J = 5.4 Hz, 1H), 6.95 - 6.84 (m, 3H), 5.62 (q, J = 7.0 Hz, 1H), 5.05 (dt, J = 8.7, 4.5 Hz , 1H), 4.53 - 4.40 (m, 1H), 4.04 (s, 3H), 1.83 - 1.66 (m, 5H), 1.29 (d, J = 6.3 Hz, 3H), 0.91 (t, J = 7.5 Hz, 3H). ¹³ C NMR (101 MHz, CDCb) δ 168.42, 158.70, 157.79, 154.19, 149.07, 145.79, 141.65, 131.53, 129.47, 121.11, 116.24, 111.29, 79.15, 74.40, 56.78, 51.61, 22.80, 15.99, 14.18, 9.81. 7 IR (thin film) 2943, 1770, 1714, 1602, 1501, 1371, 1243, 1082, 732 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C28H26F 2N2NaO7, 563,1600; found, 563.1588 ¹ H NMR (400 MHz, CDCb) δ 8.60 (d, J = 5.4 Hz, 1H), 7.14 (d, J = 5.3 Hz, 1H), 7.08 (dd, J = 8.6, 6.7 Hz, 1H), 7.03 - 6.93 (m, 2H), 6.85 (t, J = 9.3 Hz, 1H), 6.51 (dd, J = 10 , 9, 2.5 Hz, 1H), 6.38 (td, J = 8.3, 2.5 Hz, 1H), 5.68 (dq, J = 8.4, 6.2 Hz, 1H) , 5.38 (q, J = 7.1 Hz, 1H), 4.40 (d, J = 8.3 Hz, 1H), 4.06 (s, 3H), 3.72 (s, 3H) , 2.20 (d, J = 1.9 Hz, 3H), 1.51 (d, J = 7.1 Hz, 3H), 1.17 (d, J = 6.2 Hz, 3H). ¹⁹ F NMR (376 MHz, CDCb) δ 113.66, -120.64.

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IR (thin film) 2940, 1769, 1712, 1605, HRMS-ESI [M + H] + (m / z) calculated ¹ H NMR (400 MHz, CDCh) δ 8.59 (d, J = 5.3 Hz, 1 H), 7.17 - 7.04 (m, 3H), 6.37 (ddd, J = 14, 3, 11.4, 2.5 Hz, 3H), 6.24 (dd, J = 8.5, 2.5 Hz, 1H), 5.72 (dq, J = 8.7, 6.1 Hz , 1H), 5.33 (q, J = 7.0 Hz, 1H), 4.71 (d, J = 8.8 Hz, 1H), 4.05 (s, 3H), 3.75 (s , 3H), 3.73 (s, 3H), 3.73 (s, 3H), 3.66 (s, 3H), 1.51 (d, J = 7.0 Hz, 8 1503, 1371, for C 0H33N2O10, 3H), 1.18 (d, J = 6.2 Hz, 3H). 1289, 1207, 581.2130; find 1082, 1035, 729 of, 581.2142 ¹³ C NMR (101 MHz, CDCfe) δ cm ^-1 168.19, 159.20, 158.94, 158.56, 158.30, 158.11, 154.17, 148.89, 145.63, 141.63, 129.48, 129.31, 122.87, 122.24, 111.15, 104.14, 104.10, 98.89, 98.63, 74.44, 56.75, 55.59, 55.56, 55.25, 55.19, 51.40, 41.26, 29.30, 18.56, 13.95. ¹ H NMR (400 MHz, CDCfe) δ 8.56 (d, J = 5.3 Hz, 1H), 7.09 (d, J = 5.5 Hz, 1H), 6.98 (t, J = 8.2 Hz, 1H), 6.77 (t, J = 2.2 Hz, 1H), 6.71 (dd, J = 8.3, 2.5 Hz, 1H), 6.57 - 6, 51 (m, 1H), 5.45 (q, J = 7.0 Hz, 1H), 5.23 (qd, J = 6.4, 2.8 Hz, 1H), 4.35 (dd, IR (thin film) HRMS-ESI (m / z) J = 8.5, 2.8 Hz, 1H), 4.05 (s, 3H), 2964, 1768, [M + Na] + calculated 1.57 (d, J = 7.0 Hz, 3H), 1.55 - 9 1712, 1591, for 1.33 (m, 4H), 1.31 (d, J = 6.3 Hz, 1502, 1371, C25H29ClN2NaO7, 3H), 0.88 (t, J = 7.5 Hz, 4H), 0.78 1242, 1083, 729 527,1556; find (t, J = 7.4 Hz, 3H). cm ^-1 of, 527,1551 ¹³ C NMR (101 MHz, CDCh) δ 168.14, 160.27, 158.42, 153.99, 148.85, 145.64, 141.34, 134.36, 131.17, 130.04, 120.30, 116.48, 112.09, 111.25, 80.11, 73.89, 56.71, 51.40, 42.06, 21.09, 20.86, 14.01.13, 31,10,55, 10,27.

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10 IR (thin film) 2957, 1768, 1712, 1602, 1371, 1149, 1081.729 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C ₂₄ H ₂₈ N ₂ NaO ₈ , 495.1738; found, 495.1728 ¹ H NMR (400 MHz, CDCh) δ 8.56 (d, J = 5.3 Hz, 1H), 7.08 (d, J = 5.3 Hz, 1H), 6.95 (t, J = 8.2 Hz, 1H), 6.41 (dd, J = 8.3, 2.3 Hz, 1H), 6.35 (t, J = 2.4 Hz, 1H), 6.25 - 6, 19 (m, 1H), 5.47 (q, J = 7.0 Hz, 1H), 5.05 (qd, J = 6.4, 2.9 Hz, 1H), 4.42 (dt, J = 8.6, 3.4 Hz, 1H), 4.04 (s, 3H), 3.70 (s, 3H), 1.70 - 1.55 (m, 5H), 1.54 - 1, 33 (m, 2H), 1.30 (d, J = 6.4 Hz, 3H), 0.89 (t, J = 7.1 Hz, 3H). ¹³ C NMR (101 MHz, CDCfe) δ 168.16, 160.48, 160.26, 158.51, 154.10, 148.80, 145.71, 141.48, 131.36, 129.56, 111.16, 107.08, 106.78, 102.00, 78.50, 74.74, 56.67, 55.10, 51.47, 33.40, 18.87, 14.04, 13, 96, 13.64. 11 IR (thin film) 2947, 1770, 1714, 1603, 1501, 1371, 1244, 1223, 1082, 732 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C27H24F 2N2NaO6, 533.1495; found, 533.1488 ¹ H NMR (400 MHz, CDCfe) δ 8.61 (d, J = 5.3 Hz, 1H), 7.21 (dd, J = 8.6, 5.7 Hz, 1H), 7.14 ( d, J = 5.4 Hz, 1H), 7.12 - 7.07 (m, 2H), 6.99 - 6.89 (m, 2H), 6.81 - 6.69 (m, 2H) , 5.65 (dq, J = 8.3, 6.2 Hz, 1H), 5.38 (q, J = 7.1 Hz, 1H), 4.18 (d, J = 8.4 Hz, 1H), 4.06 (s, 3H), 2.17 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H), 1.20 (d, J = 6.1 Hz, 3H). ¹⁹ F NMR (376 MHz, CDCh) δ 115.78, -116.98. 12 IR (thin film) 2947, 1770, 1714, 1603, 1507, 1371, 1222, 1083, 831.734 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C26H22F 2N2NaO6, 519.1338; found, 519.1343 ¹ H NMR (400 MHz, CDCh) δ 8.57 (d, J = 5.3 Hz, 1H), 7.19 - 7.03 (m, 5H), 6.96 - 6.87 (m, 2H ), 6.84 - 6.72 (m, 2H), 5.50 (dq, J = 9.8, 6.1 Hz, 1H), 5.43 (q, J = 7.0 Hz, 1H) , 4.05 (s, 3H), 3.96 (d, J = 9.7 Hz, 1H), 1.56 (d, J = 7.0 Hz, 3H), 1.29 (d, J = 6.0 Hz, 3H). ¹⁹ F NMR (376 MHz, CDCh) δ 115.62, -115.92.

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IR (thin film) HRMS-ESI [M + H] + (m / z) calculated ¹ H NMR (500 MHz, CDCh) δ 8.59 (d, J = 5.3 Hz, 1 H), 7.26 - 7.22 (m, 2H), 7.11 (d, J = 5, 3 Hz, 1H), 6.95 - 6.86 (m, 3H), 5.60 (q, J = 7.0 Hz, 2933, 1713, 1769, 1599, 13 1499, 1370, for C 25H31N2O7, 1H), 5.08 (dt, J = 7.2, 4.8 Hz, 1H), 471.2126; find 4.47 (qd, J = 6.3, 4.5 Hz, 1H), 4.04 1240, 1079, 749 from, 471.2165 (s, 3H), 1.71 - 1.63 (m, 5H), 1.36 cm - 1.21 (m, 9H), 0.87 - 0.83 (m, 3H). ¹ H NMR (500 MHz, CDCh) δ 8.60 (d, J = 5.3 Hz, 1 H), 7.29 - 7.14 (m, 2H), 7.13 (d, J = 5, 3 Hz, 1H), 7.04 - 6.94 (m, 2H), 6.93 - 6.80 (m, IR (thin film) HRMS-ESI (m / z) 4H), 5.68 (dq, J = 8.3, 6.2 Hz, 1H), 2946, 1769, [M + H] + calculated 5.39 (q, J = 7.1 Hz, 1H), 4.06 (s, 14 1713, 1502, for C ₂₆ H23F2N2O6, 3H), 3.99 (d, J = 8.3 Hz, 1H), 1.52 1371, 1243, 497.1519; find (d, J = 7.1 Hz, 3H), 1.21 (d, J = 6.2 1081.732 cm ^-1 of, 497.1511 Hz, 3H). ¹⁹ F NMR (471 MHz, CDCh) δ 112.26 - -112.39 (m), -112.79 - - 112.95 (m). ¹ H NMR (500 MHz, CDCh) δ 8.60 (d, J = 5.3 Hz, 1H), 7.39 (dd, J = 8.8, 6.1 Hz, 1H), 7.15 - 7.09 (m, 3H), 7.06 (dd, J = 8.4, 2.6 Hz, 1H), IR (thin film) 2945, 1768, HRMS-ESI (m / z) 6.84 (tq, J = 7.4, 1.2 Hz, 1H), 6.74 [M + H] + calculated - 6.67 (m, 3H), 5.55 (d, J = 4.7 Hz, 1712, 1602, 15 for C ₂₆ H ₂₃ ClFN ₂ O ₇ , 1H), 5.52 - 5.47 (m, 1H), 5.36 - 1491, 1371, 529.1172; find 5.28 (m, 1H), 4.05 (s, 3H), 1.62 (d, 1221, 1081, 728 of, 529.1211 J = 7.0 Hz, 3H), 1.33 (d, J = 6.4 _cm ^-1 Hz, 3H). ¹⁹ F NMR (471 MHz, CDCh) δ 111.52 - -111.64 (m).

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IR (thin film) 2964, 1769, HRMS-ESI (m / z) [M + H] + calculated ¹ H NMR (500 MHz, CDCl3) δ 8.58 (d, J = 5.3 Hz, 1H), 7.12 - 7.06 (m, 2H), 6.97 (dd, J = 7.9 , 1.7 Hz, 1H), 6.92 (d, J = 8.5 Hz, 1H), 6.67 (td, J = 7.6, 1.4 Hz, 1H), 5.35 - 5 , 25 (m, 2H), 4.42 (dd, J = 8.5, 2.7 Hz, 1H), 4.05 (s, 3H), 1.68 - 1.60 (m, 2H), 1.55 - 1.49 (m, 1H), 1.49 (d, J = 7.0 Hz, 3H), 1.47 - 1.39 (m, 2H), 16 1714, 1480, 1372, 1289, for C25H30ClN2O7, 505.1736; find 1.37 (d, J = 6.4 Hz, 3H), 0.94 - 0.88 (m, 3H), 0.87 - 0.81 (m, 3H). 1244, 747 cm ^-1 of, 505,1771 ¹³ C NMR (126 MHz, CDCfe) δ 168.1, 158.3, 155.2, 154.1, 148.9, 145.6, 141.5, 131.4, 129.9, 127.6, 122, 9, 121.0, 114.6, 111.1, 81.8, 73.6, 56.7, 51.3, 41.9, 20.9, 20.9, 13.8, 13.4, 10, 8, 10.0. IR (thin film) 2945, 1769, 1712, 1502, HRMS-ESI (m / z) [M + H] + calculated ¹ H NMR (500 MHz, CDCfe) δ 8.61 (d, J = 5.3 Hz, 1 H), 7.34 - 7.03 (m, 7H), 6.79 - 6.68 (m, 2H), 5.74 - 5.63 (m, 1H), 5.36 (q, J = 7.0 Hz, 1H), 4.33 (d, J = 9.0 Hz, 1H), 4, 05 17 for C27H26FN2O6, 493.1769; found, 493.1765 (d, J = 3.1 Hz, 3H), 2.22 (s, 3H), 1.53 (d, J = 7.1 Hz, 3H), 1.22 (d, J = 6.1 Hz, 3H). 1370, 1242, 1080, 909, 727, 699 cm ^{1 19} F NMR (471 MHz, CDCh) δ 118.95 - -119.05 (m). IR (thin film) 2937, 1768, 1712, 1508, HRMS-ESI (m / z) [M + H] + calculated ¹ H NMR (500 MHz, CDCh) δ 8.60 (d, J = 5.3 Hz, 1H), 7.13 (d, J = 5.4 Hz, 1H), 7.12 - 7.07 ( m, 2H), 7.07 - 7.02 (m, 2H), 6.80 - 6.76 (m, 2H), 6.70 - 6.64 (m, 2H), 5.69 - 5, 61 (m, 1H), 5.38 (q, J = 7.1 Hz, 1H), 4.05 (s, 3H), 3.88 (d, J = 7.8 Hz, 1H), 3, 75 (s, 3H), 3.72 (s, 3H), 18 63-74 for C28H29N2O8, 521.1918; found, 521.1910 1.53 (d, J = 7.1 Hz, 3H), 1.18 (d, J = 6.3 Hz, 3H). 1370, 1242, 1177, 909, 727 cm ^{1 13} C NMR (126 MHz, CDCh) δ 168.1, 158.6, 158.2, 158.0, 154.1, 149.0, 145.6, 141.6, 133.7, 133.2, 131.4, 129.4, 129.2, 113.9, 113.5, 111.22, 74.1, 56.7, 55.2, 55.1, 55.0, 51.32, 18, 7, 13.9.

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IR (thin film) HRMS-ESI (m / z) ¹ H NMR (500 MHz, CDCh) δ 8.60 (d, J = 5.3 Hz, 1H), 7.22 (dd, J = 8.7, 5.7 Hz, 1H), 7.14 ( d, J = 5.3 Hz, 1H), 7.04 - 6.98 (m, 2H), 6.90 (td, J = 8.5, 2.9 Hz, 1H), 6.82 - 2946, 1769, [M + H] + calculated 6.74 (m, 3H), 5.69 - 5.60 (m, 1H), 1712, 1603, 5.40 (q, J = 7.1 Hz, 1H), 4.06 (d, J 19 1500, 1371, for C ₂₇ H25F 2N2Õ6, = 10.4 Hz, 1H), 4.06 (s, 3H), 2.13 511.1675; find 1244, 1222, (s, 3H), 1.54 (d, J = 7.1 Hz, 3H), of, 511,1671 1082, 729 cm ^-1 1.24 (d, J = 6.4 Hz, 3H). ¹⁹ F NMR (471 MHz, CDCfe) δ 116.18 - -116.28 (m), -116.42 - - 116.51 (m). ¹ H NMR (500 MHz, CDCfe) δ 8.60 (d, J = 5.3 Hz, 1H), 7.17 - 7.11 (m, 3H), 7.06 (dd, J = 8.6 , 6.6 Hz, 1H), 6.91 (t, J = 8.7 Hz, 2H), 6.50 (dd, J = 10.9, 2.6 Hz, 1H), 6.37 (td , J = IR (thin film) 2942, 1769, HRMS-ESI (m / z) 8.3, 2.5 Hz, 1H), 5.69 (dq, J = 8.2, [M + H] + calculated 6.2 Hz, 1H), 5.39 (q, J = 7.0 Hz, 1712, 1601, 20 for C ₂₇ H25F2N2O7, 1H), 4.44 (d, J = 8.1 Hz, 1H), 4.06 1501, 1371, 527.1624; find (s, 3H), 3.71 (s, 3H), 1.51 (d, J = 1243, 1222, of, 527.1622 7.1 Hz, 3H), 1.17 (d, J = 6.2 Hz, 1081, 729 cm ^-1 3H). ¹⁹ F NMR (471 MHz, CDCh) δ 113.45 - -113.58 (m), -116.27 - - 116.40 (m). ¹ H NMR (500 MHz, CDCh) δ 8.59 (d, J = 5.3 Hz, 1 H), 7.36 - 7.32 (m, 2H), 7.30 - 7.24 (m, 2H), 7.21 (dd, J = 7.9, 1.8 Hz, 2H), 7.12 (d, J = 5.4 Hz, 1H), 7.01 - 6.95 (m, 1H ), 6.77 (td, J = 7.7, 1.4 Hz, 1H), 6.66 IR (thin film) 2944, 1767, HRMS-ESI (m / z) (dd, J = 8.3, 1.4 Hz, 1H), 5.51 (q, J [M + H] + calculated = 7.1 Hz, 1H), 5.36 - 5.25 (m, 2H), 1743, 1710, 21 for C ₂₆ H24ClN2O7, 4.05 (s, 3H), 1.61 (d, J = 7.0 Hz, 1481, 1370, 511.1267; find 3H), 1.32 (d, J = 6.3 Hz, 3H). 1243, 730, 701 of, 511,1304 _cm ^{-1 13} C NMR (126 MHz, CDCh) δ 168.1, 158.6, 154.1, 153.3, 149.0, 145.7, 141.6, 136.6, 131.4, 130.1, 128, 5, 128.1, 127.5, 126.6, 123.4, 121.7, 115.2, 111.2, 81.9, 75.1, 56.8, 51.4, 13.9, 13, 7.

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IR (thin film) 2944, 1769, 1712, 1501, HRMS-ESI [M + H] + (m / z) calculated ¹ H NMR (500 MHz, CDCb) δ 8.60 (d, J = 5.3 Hz, 1H), 7.21 - 7.08 (m, 6H), 7.05 - 6.95 (m, 2H ), 6.89 - 6.83 (m, 1H), 5.68 (dq, J = 8.3, 6.2 Hz, 1H), 5.35 (q, J = 7.1 Hz, 1H) , 4.06 (s, 3H), 3.93 (d, J = 8.3 Hz, 22 1370, 1241, for C ₂₇ H26FN2O6, 1H), 2.20 (d, J = 2.0 Hz, 3H), 1.49 493.1769; find 1080, 727, 698 (d, J = 7.1 Hz, 3H), 1.20 (d, J = 6.2 of, 493.1767 cm ¹ Hz, 3H). ¹⁹ F NMR (471 MHz, CDCb) δ 120.34 - -120.43 (m). IR (thin film) ¹ H NMR (500 MHz, CDCb) δ 8.57 (d, J = 5.3 Hz, 1H), 7.10 (d, J = 5.3 Hz, 1H), 6.85 - 6.74 ( m, 4H), 5.69 (q, J = 7.0 Hz, 1 H), 5.02 (t, J = 5.6 Hz, 1H), 4.37 - 4.29 (m, 1H) , 4.03 (s, 3H), 3.74 (s, 3H), 2.10 (qd, J = HRMS-ESI (m / z) 7.0, 5.8 Hz, 1H), 1.74 (d, J = 7.1 2965, 1769, [M + H] + calculated Hz, 3H), 1.24 (d, J = 6.3 Hz, 3H), 1712, 1504, 23 for C 24H29N2O8, 0.99 (d, J = 6.9 Hz, 3H), 0.94 (d, J 1370, 1217, 473.1918; find = 6.9 Hz, 3H). 1079, 909, 729 of, 473.1910 cm ^{1 13} C NMR (126 MHz, CDCb) δ 168.3, 158.7, 154.1, 154.1, 151.4, 149.0, 145.8, 141.6, 131.5, 117.4, 114.6, 111.2, 80.8, 73.9, 56.7, 55.6, 51.6, 28.8, 19.4, 17.4, 15.6, 14.1. IR (thin film) ¹ H NMR (500 MHz, CDCb) δ 8.55 (d, J = 5.4 Hz, 1H), 7.08 (d, J = 5.4 Hz, 1H), 7.02 - 6.95 ( m, 1H), 6.59 (dd, J = 8.4, 2.4 Hz, 1H), 6.47 (dt, J = 11.1.2.3 Hz, 1H), 6.29 (td , J = HRMS-ESI (m / z) 8.2, 2.4 Hz, 1H), 5.46 - 5.39 (m, 2964, 1768, [M + Na] + calculated 1H), 5.23 - 5.18 (m, 1H), 4.12 (dd, 1712, 1603, 24 for C ₂₃ H ₂₅ FN ₂ O ₇ Na, J = 8.5, 2.8 Hz, 1H), 4.03 (d, J = 1372, 1317, 483.1538; find 1.9 Hz, 3H), 1.93 - 1.83 (m, 1H), 1243, 1132, 732 483.1525 1.55 (d, J = 7.1 Hz, 3H), 1.30 (d, J cm = 6.4 Hz, 3H), 0.96 (d, J = 6.8 Hz, 3H), 0.93 (d, J = 6.8 Hz, 3H). ¹⁹ F NMR (471 MHz, CDCb) δ 112.00 - -112.27 (m).

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IR (thin film) HRMS-ESI [M + Na] + (m / z) calculated ¹ H NMR (500 MHz, CDCb) δ 8.61 (d, J = 5.3 Hz, 1 H), 7.17 - 7.04 (m, 6H), 6.72 (d, J = 9, 2 Hz, 2H), 5.64 (dq, J = 9.4, 6.1 Hz, 1H), 5.35 (q, J = 7.0 Hz, 1H), 4.29 (d, J = 9.1 Hz, 1H), 4.06 (s, 3H), 2.28 (s, 3H), 2.22 (s, 3H), 1.53 (d, J = 7.1 Hz, 3H) , 1.22 (d, J = 6.1 Hz, 3H). 2944, 1715, 1770, 1602, 25 1502, 1453, for C28H2- FN2O6Na, ¹³ C NMR (126 MHz, CDCb) δ 1371, 1289, 529.1745; find 168.16, 160.46 (d, J = 244.3 Hz), 1243, 1106, of, 529.1738 158.54, 154.14, 148.99, 145.65, 1081.729 cm ^-1 141.60, 138.26, 137.27, 136.46, 131.57, 129.35, 128.38 (d, J = 4.7 Hz), 125.19 (d, J = 14.5 Hz), 124.68, 115.82 (d, J = 22.7 Hz), 111.16, 73.82, 56.77, 53.78, 51.27, 47.98, 29.28, 20.98, 20.88, 18.74, 13.92. ¹ H NMR (500 MHz, CDCb) δ 8.61 (d, J = 5.3 Hz, 1H), 7.14 (d, J = 5.3 Hz, 1H), 7.07 (dd, J = 8.2, 6.3 Hz, 2H), 6.85 (dd, J = 8.2, 2.0 Hz, 1H), 6.75 (dd, J = 11.7, 2.1 Hz, 2H ), 6.59 (dd, J = 8.2, 2.1 Hz, 1H), 5.72 (dq, J = 8.1.6.2 Hz, 1H), 5.40 (q, J IR (thin film) 2943, 1769, = 7.1 Hz, 1H), 4.75 (d, J = 7.8 Hz, HRMS-ESI (m / z) 1H), 4.06 (d, J = 1.6 Hz, 3H), 3.72 1714, 1593, [M + H] + calculated (s, 3H), 3.70 (s, 3H), 1.52 (d, J = 1501, 1490, 26 for C ₂₈ H 27Cl2N2O8, 7.0 Hz, 3H), 1.18 (d, J = 6.2 Hz, 1454, 1371, 589,1139; find 3H). 1289, 1244, of, 589,1163 1101, 1082, ¹³ C NMR (126 MHz, CDCb) δ 1030, 730 cm 168.10, 158.56, 157.94, 157.65, 154.12, 149.04, 145.62, 141.58, 133.06, 132.59, 131.45, 129.96, 129.71, 128.18, 127.32, 120.49, 119.92, 111.57, 111.44, 111.30, 73.42, 56.78, 55.72, 51.29, 41.66, 18.49, 13.90. ¹ H NMR (500 MHz, CDCb) δ 8.61 IR (thin film) HRMS-ESI (m / z) (d, J = 5.3 Hz, 1 H), 7.24 - 7.19 (m, 2943, 1769, 2H), 7.15 (d, J = 5.3 Hz, 1H), 7.12 [M + H] + calculated 1715, 1602, - 6.99 (m, 6H), 5.67 (p, J = 6.3 Hz, 27 1501, 1371, for C ₂₆ H 23Cl2N2O6, 1H), 5.44 (q, J = 6.9 Hz, 1H), 4.07 529.0928; find 1321, 1243, (s, 3H), 3.97 (d, J = 7.2 Hz, 1H), of, 529.0933 1089.732 cm ^-1 1.60 - 1.45 (m, 3H), 1.20 (d, J = 6.2 Hz, 3H).

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28 IR (thin film) 2945, 1769, 1714, 1602, 1501, 1453, 1371, 1325, 1289, 1243, 1113, 1067, 735 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C27H23F 3N2O6Na, 551,1400; found, 551.1408 ¹ H NMR (500 MHz, CDCh) δ 8.61 (d, J = 5.3 Hz, 1H), 7.50 (d, J = 8.1 Hz, 2H), 7.34 (d, J = 8.1 Hz, 2H), 7.23 - 7.10 (m, 6H), 5.77 (dq, J = 7.8, 6.2 Hz, 1H), 5.39 (q, J = 7 , 1 Hz, 1H), 4.16 - 4.07 (m, 1H), 4.06 (s, 3H), 1.52 (d, J = 7.1 Hz, 3H), 1.22 (d , J = 6.2 Hz, 3H). 29 IR (thin film) 2946, 1769, 1741, 1714, 1602, 1506, 1454, 1371, 1289, 1219, 733 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C26H22F 2N2O6Na, 519.1338; found, 519.1332 ¹ H NMR (500 MHz, CDCfe) δ 8.57 (d, J = 5.3 Hz, 1H), 7.18 - 7.03 (m, 5H), 6.92 (t, J = 8.6 Hz, 2H), 6.78 (t, J = 8.7 Hz, 2H), 5.50 (dq, J = 9.8, 6.0 Hz, 1H), 5.43 (q, J = 7 , 0 Hz, 1H), 4.06 (s, 3H), 3.96 (d, J = 9.7 Hz, 1H), 1.56 (d, J = 7.9 Hz, 3H), 1, 29 (d, J = 6.0 Hz, 3H). ¹³ C NMR (126 MHz, CDCfe) δ 168.12, 161.36 (d, J = 245.2 Hz), 158.49, 154.07, 148.97, 145.34, 141.32, 136, 77, 131.14, 129.50 (d, J = 7.8 Hz), 129.20 (d, J = 7.8 Hz), 115.66 (d, J = 21.4 Hz), 115, 26 (d, J = 21.2 Hz), 111.14, 74.29, 56.73, 55.90, 53.78, 51.18, 31.75, 29.28, 18.73, 13, 58. 30 IR (thin film) 2968, 1770, 1742, 1715, 1602, 1507, 1453, 1370, 1289, 1229, 1079, 747 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C24H28N2O7Na, 479.1789; found, 479.1763 ¹ H NMR (500 MHz, CDCh) δ 8.58 (d, J = 5.3 Hz, 1H), 7.11 (d, J = 5.3 Hz, 1H), 7.05 - 7.00 ( m, 2H), 6.75 (d, J = 8.5 Hz, 2H), 5.70 (q, J = 7.0 Hz, 1H), 5.04 (t, J = 5.6 Hz, 1H), 4.41 (p, J = 6.1 Hz, 1H), 4.04 (s, 2H), 2.26 (s, 3H), 2.15 - 2.06 (m, 1H), 1.75 (d, J = 7.1 Hz, 3H), 1.27 - 1.23 (m, 3H), 1.00 (d, J = 6.9 Hz, 2H), 0.93 (d , J = 6.7 Hz, 3H). ¹³ C NMR (126 MHz, CDCh) δ 168.27, 158.75, 155.20, 154.14, 149.04, 145.81, 141.62, 131.54, 130.31, 129.94, 115.87, 111.23, 80.89, 72.78, 56.76, 51.67, 29.28, 28.85, 20.50, 19.38, 17.31, 15.57, 14, 19.

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31 IR (thin film) 2957, 1768, 1740, 1713, 1601, 1506, 1453, 1370, 1321, 1288, 1241, 1106, 1081.733 cm ^-1 HRMS-ESI (m / z) [M + H] + calculated for C24H29N2O7, 457.1969; found, 457.1963 ¹ H NMR (500 MHz, CDCb) δ 8.57 (d, J = 5.3 Hz, 1H), 7.08 (d, J = 5.3 Hz, 1H), 6.89 (d, J = 8.1 Hz, 2H), 6.73 (d, J = 8.6 Hz, 2H), 5.48 (q, J = 7.0 Hz, 1H), 5.07 (qd, J = 6, 5, 3.1 Hz, 1H), 4.33 (dt, J = 8.6, 3.6 Hz, 1H), 4.03 (s, 3H), 2.18 (s, 3H), 1, 66 - 1.57 (m, 4H), 1.54 - 1.43 (m, 2H), 1.38 - 1.32 (m, 1H), 1.29 (d, J = 6.4 Hz, 2H), 0.88 (t, J = 7.1 Hz, 3H). ¹³ C NMR (126 MHz, CDCb) δ 168.14, 158.54, 156.98, 154.06, 148.90, 145.69, 141.47, 131.44, 129.99, 129.67, 115.90, 111.08, 79.28, 74.58, 56.72, 53.78, 51.52, 33.49, 29.28, 20.47, 18.88, 14.01, 13, 83. 32 IR (thin film) 2945, 1769, 1714, 1602, 1501, 1453, 1370, 1242, 1081.730 cm ^-1 HRMS-ESI (m / z) [M + Na] + calculated for C28H28N2O6Na, 511.1840; found, 511.1828 ¹ H NMR (500 MHz, CDCb) δ 8.61 (d, J = 5.4 Hz, 1H), 7.13 (d, J = 5.4 Hz, 1H), 7.09 - 6.99 ( m, 6H), 6.94 (d, J = 7.8 Hz, 2H), 5.70 (dq, J = 8.5, 6.2 Hz, 1H), 5.37 (q, J = 7 , 1 Hz, 1H), 4.06 (s, 3H), 3.90 (d, J = 8.1 Hz, 1H), 2.26 (s, 3H), 2.21 (s, 3H), 1.52 (d, J = 7.1 Hz, 3H), 1.19 (d, J = 6.1 Hz, 3H).

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IR (thin film) HRMS-ESI [M + Na] + calc (m / z) ulado ¹ H NMR (500 MHz, CDCh) δ 8.62 (d, J = 5.3 Hz, 1H), 7.25 - 7.21 (m, 1H), 7.14 (d, J = 5.3 Hz, 1H), 6.99 - 6.92 (m, 4H), 6.88 (td, J = 8.5, 2.9 Hz, 1H), 6.76 (dd, J = 9.7, 2.8 Hz, 1H), 5.67 (dq, J = 8.1, 6.2 Hz, 1H), 5.36 (q, J = 7.0 Hz, 1H), 4.08 (d, J = 8.1 Hz, 1H), 4.06 (s, 3H), 2.21 (s, 3H), 2.19 (s, 3H), 1.53 (d, J = 7.0 Hz, 3H), 1.23 (d, J = 6.2 Hz, 3H). 2945, 1714, 1769, 1602, 33 1499, 1453, for C ₂₈ H ₂₇ FN ₂ O ₆ Na, 1370, 1288, 529.1745; find ¹³ C NMR (126 MHz, CDCh) δ 1243, 1082, 731 of, 529.1747 167.95, 161.10 (d, J = 244.7 Hz), cm ^-1 158.53, 154.13, 149.04, 145.60, 141.57, 138.67 (d, J = 7.5 Hz), 136.84, 135.95, 135.60 (d, J = 3.3 Hz), 131.50, 128.74 (d, J = 19.5 Hz), 128.49 (d, J = 8.2 Hz), 117.23 (d, J = 20.9 Hz), 112.83 (d, J = 20.7 Hz), 111.23, 74.38, 56.77, 51.22, 50.98, 20.94, 20.22, 18.64, 13.92. ¹ H NMR (500 MHz, CDCh) δ 8.61 IR (thin film) HRMS-ESI (m / z) (d, J = 5.3 Hz, 1H), 7.11 (ddd, J = 2945, 1768, 24.7, 8.8, 5.3 Hz, 5H), 6.95 (t, J = [M + Nal calculated 1713, 1602, for 8.6 Hz, 2H), 6.82 (t, J = 8.7 Hz, 34 1505, 1454, 2H), 5.66 (p, J = 6.3 Hz, 1H), 5.42 C26H22F2N2O6Na, 1371, 1321, (q, J = 7.0 Hz, 1H), 4.06 (s, 3H), 519.1338; find 1222, 1081, of, 519.1337 3.98 (d, J = 7.2 Hz, 1H), 1.55 (d, J 833, 732 cm ^- ' = 5.3 Hz, 3H), 1.20 (d, J = 6.2 Hz, 3H). ¹ H NMR (500 MHz, CDCh) δ 8.59 (d, J = 5.3 Hz, 1H), 7.27 - 7.21 (m, IR (thin film) HRMS-ESI (m / z) 2H), 7.12 (dd, J = 5.4, 2.0 Hz, 1H), 2959, 1769, 6.93 - 6.85 (m, 3H), 5.65 - 5.57 [M + Hl ⁺ calculated 1715, 1600, (m, 1H), 5.11 (dt, J = 8.7, 4.6 Hz, 35 for C ₂₃ H ₂₇ N2O7, 1500, 1454, 1H), 4.46 (td, J = 6.4, 4.3 Hz, 1H), 443.1813; find 1371, 1241, 443,1807 4.04 (d, J = 2.0 Hz, 3H), 1.74 - 1080, 748 cm ^-1 1.62 (m, 5H), 1.44 - 1.36 (m, 1H), 1.34 - 1.27 (m, 4H), 0.95 - 0.86 (m, 3H).

* Compound # - compound number

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Table 3. Biological Test Classification Scale

Classification table for fungal pathogens % of control Classification > 80 THE <80 B Not tested Ç No activity observed in the Reported Trial D

Table 4. Biological activity - PUCCRT and SEPTTR disease control in high and low volume applications

LV activity at 121.5 g / H PUCCRT * SEPTTR * Compound No. 1DP * 3DC * 1DP * 3DC * 1 THE B THE THE 2 THE B THE THE 3 D D D D 4 THE THE D B 5 THE B THE B 6 D B D B 7 THE D THE THE 8 B B THE THE 9 THE B B B 10 THE THE D THE 11 B D THE THE 12 D D D D 13 D D B B 14 B B THE THE 15 THE B THE THE 16 THE B B THE 17 THE D THE THE

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LV activity at 121.5 g / H PUCCRT ‘ SEPTTR ‘ Compound No. 1DP ‘ 3DC ‘ 1DP ‘ 3DC ‘ 18 THE B THE THE 19 THE B THE THE 20 THE B THE THE 21 THE D THE B 22 THE B THE THE 23 THE THE B THE 24 THE THE B THE 25 THE B THE THE 26 THE D THE THE 27 B D THE THE 28 B B THE THE 29 D D D B 30 THE B B B 31 THE B D B 32 THE B THE THE 33 THE B THE THE 34 D D D D 35 D D D B

'Compound No. - Compound Number' PUCCRT - Brown Rust of Wheat (Puccinia triticina) 'SEPTTR - Wheat Leaf Stain (Zymoseptoria tritici)' 1DP - 1 Day Protection '3DC - 3 Day Healing' g / H - Grams per Hectare ^' ppm - Parts per million

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Table 5. Biological activity - Disease control at 25 ppm

PHAKPA * Compound No. 1DP * 3DC * 1 B D 13 D B 18 B B 19 THE B 21 D B 22 B B 23 THE B 24 THE B 25 B D 26 B D 27 B B 28 D B 29 D B 30 B D 31 B B 32 B B 33 THE B 34 B B 35 D B

‘Compound # - compound number‘ PHAKPA - Asian Soybean Rust (Phakopsora pachyrhizi) ‘1DP - 1 Day Protection‘ 3DC - 3 Day Healing

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Claims (9)

1. Composition for the control of a fungal pathogen, characterized by the fact that it includes mixtures of at least one of the compounds of Formula I, in which: R ₁ is hydrogen or C ₁ - C ₅ alkyl, each optionally substituted by 0, 1 or multiple R ₆ ; R ₂ is hydrogen, C ₁ - C ₅ alkyl or cycloalkyl, each optionally substituted by 0, 1 or multiple R ₆ ; R ₃ is alkyl, cycloalkyl, aryl or heteroaryl, each optionally substituted by 0, 1 or multiple R ₆ ; R ₄ is hydrogen, halo, hydroxyl, alkyl or alkoxy; R ₅ is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, thioalkyl, thioaryl or heterothioaryl, each optionally substituted by 0, 1 or multiple R ₆ ; R ₆ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano or heterocyclyl, each optionally substituted by 0, 1 or multiple R ₇ ; R ₇ is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl; and R ₈ is hydrogen or C1 - C5 alkyl, each optionally substituted by 0, 1 or multiple R ₆ , and a phytologically acceptable carrier material. 2. Composition according to claim 1, characterized by the fact that R1 and R8 are independently hydrogen or Petition 870170063491, of 29/08/2017, p. 9/137 2/3 C ₁ - C ₅ alkyl. 3. Composition according to claim 2, characterized by the fact that R ₂ is C ₁ - C ₅ alkyl. 4. Composition according to claim 2, characterized by the fact that R ₃ and R ₅ are independently aryl, each optionally substituted by 0, 1, or multiple R ₆ . 5. Composition according to claim 2, characterized by the fact that R ₄ is hydrogen. 6. Composition according to claim 2, characterized by the fact that R ₁ and R ₈ are independently hydrogen or C ₁ - C ₅ alkyl, R ₂ is C ₁ - C ₅ alkyl, and R ₃ and R ₅ are independently aryl, each optionally substituted by 0, 1 or multiple R6, and R4 is hydrogen. 7. Composition, according to claim 1, characterized by the fact that the fungal pathogen is one among Wheat Leaf Spot (Zymoseptoria tritici), Brown Wheat Rust (Puccinia triticina), Striated Rust (Puccinia striiformis), Scabies of the Apple Tree (Venturia inaequalis), Common Corn Coal (Ustilago maydis), Powdery Mildew (Uncinula necator), Barley Scald (Rhynchosporium secalis), Rice Blast (Pyricularia oryzae), Soybean Rust (Phakopsora pachyrhizi), Manuma da Pachyrhizi Wheat (Leptosphaeria nodorum), Wheat Mildew (Blumeria graminis f. Sp. Tritici), Barley Mildew (Blumeria graminis f. Sp. Hordei), Cucurbit Mildew (Erysiphe cichoracearum), Cucurbitaceae Anthracnose (Colletotrichum) Beet (Cercospora beticola), Pinta Preta do Tomate (Alternaria solani) and Reticular Spot of Barley (Pyrenophora teres). 8. Composition, according to claim 6, characterized by the fact that the fungal pathogen is one of the Wheat Leaf Spot (Zymoseptoria tritici), Brown Rust (Puccinia Petition 870170063491, of 29/08/2017, p. 10/137 3/3 trithycin), Apple Scab (Venturia inaequalis), Barley Scald (Rhynchosporium secalis), Rice Blast (Pyricularia oryzae), Soybean Rust (Phakopsora pachyrhizi), Wheat Glaze (Leptosphaeria nodorumum), Cucurbits (Colletotrichum lagenarium), Beet Leaf Spot (Cercospora beticola) and Pinta Preta do Tomate (Alternaria solani). 9. Method for control and prevention of fungal attack in a plant characterized by the fact that the method includes the step of: Apply a fungicidally effective amount of at least one of the compositions, as defined in claim 6, to at least one of the plant, an area adjacent to the plant, the soil adapted to support the growth of the plant, a plant root, and the foliage of the plant. Petition 870170063491, of 29/08/2017, p. 11/137 1/1