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(19) TZZ ¥___T

(11) EP 2 317 851 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 43/54 (2006.01) A01P 3/00 (2006.01) 15.01.2014 Bulletin 2014/03 A01P 7/04 (2006.01)

(21) Application number: 09807658.1 (86) International application number: PCT/US2009/052404 (22) Date of filing: 31.07.2009 (87) International publication number: WO 2010/047866 (29.04.2010 Gazette 2010/17)

(54) USE OF 5-FLUOROCYTOSINE AS A FUNGICIDE VERWENDUNG VON 5-FLUORCYTOSIN ALS FUNGIZID UTILISATION DE 5-FLUOROCYTOSINE EN TANT QUE FONGICIDE

(84) Designated Contracting States: • LORSBACH, Beth AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Indianapolis, IN 46220 (US) HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL • MEYER, Kevin PT RO SE SI SK SM TR Zionsville, IN 46077 (US) • OWEN, W. (30) Priority: 01.08.2008 US 137736 P Carmel, IN 46033 (US) • SULLENBERGER, Michael (43) Date of publication of application: Westfield, IN 46074 (US) 11.05.2011 Bulletin 2011/19 • WEBSTER, Jeffery New Palestine, IN 46163 (US) (60) Divisional application: • YOUNG, David 13173978.1 / 2 647 287 Carmel, IN 46033 (US) • YAO, Chenglin (73) Proprietor: Dow AgroSciences LLC Westfield, IN 46074 (US) Indianapolis IN 46268-1054 (US) (74) Representative: Dey, Michael et al (72) Inventors: Weickmann & Weickmann • BENKO, Zoltan Patentanwälte Indianapolis, IN 46240 (US) Postfach 860820 • BRYAN, Kristy 81635 München (DE) Carmel, IN 46033 (US) • DAVIS, George (56) References cited: Carmel, IN 46032 (US) WO-A2-2004/089396 WO-A2-2009/094442 • EPP, Jeffrey US-A- 3 368 938 Noblesville, IN 46062 (US)

Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 317 851 B1

Printed by Jouve, 75001 PARIS (FR) EP 2 317 851 B1

Description

Field of the Invention

5 [0001] This present disclosure is related to the field of 5-fluorocytosine and to the use of this compound as a fungicide.

Background and Summary of the Invention

[0002] Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage 10 caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less. [0003] The present disclosure relates to 5- fluorocytosine and its use as fungicide. 5- Fluorocytosine may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes. [0004] One embodiment of the present disclosure includes a method of controlling a pathogen induced disease in a 15 plant that is at risk of being diseased from the pathogen comprising contacting one of the plant and an area adjacent to the plant with a composition including 5-fluorocytosine. [0005] US3368938 discloses the use of 5-fluorocytosine in the control of fungi.

Detailed Description of the Present Disclosure 20 [0006] The present invention is defined by the appended set of claims. [0007] The compound of the present disclosure may be purchased commercially or prepared from known methods in the literature, such as Duschinsky, R. ct art. J. Med Chem. 1966, 9, 566-572; Duschinsky, R, and Hoffer, M. U.S. Patent 3,309,359, 1967; Li, J. et al. WO 2005/080351 A1, 2005; and Bautista Rodriguez, J. et al. WO 2009/071726 A1, 2009. 25 [0008] The compound of the present disclosure may be applied by any of a variety of known techniques, either as the compound or as formulations comprising the compound. For example, the compound may be applied to the roots, seeds or foliage of plants for the control of various fungi, without damaging the commercial value of the plants. The materials may be applied in the form of any of the generally used formulation types, for example, as solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates. 30 [0009] Preferably, the compound of the present disclosure is applied in the form of a formulation, including at least 5- fluorocytosine with a phytologically acceptable carrier. Concentrated formulations may be dispersed in water, or other liquids, for application, or formulations may be dust- like or granular, which may then be applied without further treatment. The formulations can be prepared according to procedures that are conventional in the agricultural chemical art. [0010] The present disclosure contemplates all vehicles by which the compound may be formulated for delivery and 35 use as a fungicide. Typically, formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions may be produced from water-soluble, water suspendable, or emulsifiable formulations which are solids, usually known as wettable powders; or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. As will be readily appreciated, any material to which the compound may be added may be used, provided it yields the desired utility without significant interference with the activity of the compound as a antigungal 40 agent. [0011] Wettable powders, which may be compacted to form water dispersible granules, comprises an intimate mixture including 5-fluorocytosine, an inert carrier and surfactants. The concentration of the compound in the wettable powder may be from about 10 percent to about 90 percent by weight based on the total weight of the wettable powder, more preferably about 25 weight percent to about 75 weight percent. In the preparation of wettable powder formulations, the 45 compounds may be compounded with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller’s earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates or the like. In such operations, the finely divided carrier and surfactants are typically blended with the compound(s) and milled. [0012] Emulsifiable concentrates of 5-fluorocytosine may comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of the compound, in a suitable liquid, based on the total weight of the 50 concentrate. The compound may be dissolved in an inert carrier, which is either a water-miscible solvent or a mixture of water-immiscible organic solvents, and emulsifiers. The concentrates may 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 naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex 55 alcohols, such as 2-ethoxyethanol. [0013] Emulsifiers which may be advantageously employed herein may be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers

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and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or poly- oxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil- soluble salts or sulfated polyglycol ethers and 5 appropriate salts of phosphated polyglycol ether. [0014] Representative organic liquids which may be employed in preparing the emulsifiable concentrates of the com- pound of the present invention are the 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 the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether 10 or methyl ether of diethylene glycol, and the methyl ether of thriethylene glycol and the like, Mixtures of two or more organic liquids may also be employed in the preparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with the compound. The formulations can also contain other compatible additives, for 15 example, plant growth regulators and other biologically active compounds used in agriculture. [0015] Aqueous suspensions including water-insoluble 5-fluorocytosine may be dispersed in an aqueous vehicle at a concentration in the range from about 5 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding the compound, and vigorously mixing the ground material into a vehicle comprised of water and surfactants chosen from the same types discussed above. Other components, such as inorganic 20 salts and synthetic or natural gums, may also be added to increase the density and viscosity of the aqueous vehicle. [0016] 5-Fluorocytosine may also be applied as granular formulations, which are particularly useful for applications to the soil. 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, dispersed in an inert carrier which consists entirely or in large part of coarsely divided inert material such as attapulgite, bentonite, diatomite, clay or a similar inexpensive substance, Such 25 formulation are usually prepared by dissolving the compounds in a suitable solvent and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to about 3 mm. A suitable solvent is a solvent in which the compound is substantially or completely soluble. Such formulations may also be prepared by making a dough or paste of the carrier and the compound and solvent, and crushing and drying to obtain the desired granular particle. 30 [0017] Dusts containing 5-fluorocytosine may be prepared by intimately mixing one or more of the compounds in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock; and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compound, based on the total weight of the dust. [0018] The formulations may additionally contain adjuvant surfactants to enhance deposition, wetting and penetration 35 of the compound onto the target crop and organism. These adjuvant surfactants may optionally be employed as a component of the formulation or as a tank mix. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percentby volume, basedon a spray- volume of water, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulphosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or 40 vegetable oils. The formulations may also include oil- in-water emulsions such as those disclosed in U.S. Patent Appli- cation Serial No. 11/495,228. [0019] The formulations may optionally include combinations that contain other pesticidal compounds. Such additional pesticidal compounds may be fungicides, , herbicides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with 5- fluorocytosine in the medium selected for application, and not antag- 45 onistic to the activity of 5- fluorocytosine. Accordingly, in such embodiments, the other pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use. 5- Fluorocytosine and the pesticidal compound in the combination can generally be present in a weight ratio of from 1: 100 to 100:1. 1. [0020] The compound of the present disclosure may also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof, The fungicidal compound of the present disclosure are often applied in conjunction 50 with one or more other fungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), 5-Fluorocytosine may be formulated with the other fungicide(s), tank mixed with the other fungicide(s) or applied sequentially with the other fungicide(s). Such other fungicides may include 2-(thiocyanatomethylthio)-benzothi- azole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, aza- conazole, azoxystrobin, Bacillus subtilis, benalaxyl, benomyl, benthiavalicarb- isopropyl, benzylaminobenzene-sulfonate 55 (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin- S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, , carboxin, carpropamid, carvone, chlo- roneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil,

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dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base, edifenphos, enestrobin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, 5 fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonill, fenpropidin, fenpropimorph, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, flu- quinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fu- beridazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY- 81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilate), ipconazole, 10 iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hy- drate, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, mefenoxam, metalaxyl-M, metam, metam-ammonium, metam-potassi- um, metam-sodium metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty ac- 15 ids), orysastrobin, oxadixyl, oxine- copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencyeuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, , propamocarb hydrochloride, propiconazole, propineb, proquina- zid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, 20 pyrimethanil, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z071, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thi- ophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tride- morph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, zira m, 25 zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., RS ( )-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro- 1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imida- zolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methox- yethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl) 30 phenyl thiocyanateme, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, ben- taluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis (3-phenylsalicylate), copper zinc chromate, cufraneb, cupric hydrazin- ium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dime- 35 thirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furonazole-cis, furmecyclox, furo- phanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfo- 40 nanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinac- etol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, XRD-563, and zarilamid, IK-1140, and any combinations thereof. 45 [0021] Additionally, the compound of the present disclosure may be combined with other pesticides, including insec- ticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the com- pound of the present disclosure in the medium selected for application, and not antagonistic to the activity of the present compound to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal compound of the present disclosure may be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests. When 50 used in conjunction with other pesticides, 5-fluorocytosine may be formulated with the other pesticide(s), tank mixed with the other pesticide(s) or applied sequentially with the other pesticide(s). Typical insecticides include, but are not limited to: antibiotic insecticides such as allosamidin and thuringiensin; macrocyclic lactone insecticides such as and spinetoram; avermectin insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; arsenical in- 55 secticides such as , copper acetoarsenite, copper arsenate, lead arsenate, potassium arsenite and sodiumarsenite; botanical insecticides suchas , ,d- , nicotine, , einerins, cinerin I, cinerin II, jasmolin I, jasmolin II, I, pyrethrin II, quassia, rotenone, ryania and sabad illa; insecticides such as and calbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb, , carbo-

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sulfan, decarbofuran and furathiocarb; dimethylcarbamate insecticides dimitan, , hyquincarb and ; oxime carbamate insecticides such as alanycarb, , aldoxycarb, , butoxycarboxim, , nitri- lacarb, , tazimcarb, thiocarboxime, thiodicarb and ; phenyl methylcarbamate insecticides such as allyx- ycarb, , bufencarb, butacarb, carbanolate, cloethocarb, dicresyl, dioxacarb, EMPC, , fenethacarb, 5 , isoprocarb, , , mexacarbate, promacyl, , , trimethacarb, XMC and xylylcarb; dessicant insecticides such as , diatomaceous earth and silica gel;diamide insecticides such as , and ; dinitrophenol insecticides such as dinex, dinoprop, dinosam and DNOC; fluorine insecticides such as barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfluramid; formamidine insecticides such as , , and ; fumigant insec- 10 ticides such as acrylonitrile, carbon disulfide, , chloroform, chloropicrin, para-dichlorobenzene, 1,2- dichloropropane, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, hydrogen cyanide, iodomethane, methyl bromide, methylchlorofom, methylene chloride, naphthalene, phosphine, sulfuryl fluoride and tetrachloroethane; inorganic insecticides such as borax, calcium polysulfide, copper oleate, mercurous chloride, potassium thiocyanate and sodium thiocyanate; chitin synthesis inhibitors such as bistrifluron, , chlorfluazuron, , difluben- 15 zuron, flucycloxuron, , hexaflumuron, , novaluron, noviflumuron, penfluron, teflubenzuron and triflumuron; juvenile hormone mimics such as epofenonane, , , kinoprene, , pyriprox- yfen and triprene; juvenile hormones such as juvenile hormone I, juvenile hormone II and juvenile hormone III; moulting hormone agonists such as chromafenozide, halofenozide, methoxyfenozide and ; moulting hormones such as α-ecdysone and ecdysterone; moulting inhibitors such as diofenolan; precocenes such as precocene I, precocene 20 II and precocene III; unclassified insect growth regulators such as dicyclanil; analogue insecticides such as bensultap, cartap, thiocyclam and thiosultap; nicotinoid insecticides such as flonicamid; nitroguanidine insecticides such as , , and ; nitromethylene insecticides such as and nithi- azine; pyridylmethyl-amine insecticides such as , imidacloprid, nitenpyram and ; organochlorine insecticides such as bromo-DDT, camphechlor, DDT, pp’- DDT, ethyl-DDD, HCH, gamma-HCH, , , 25 pentachlorophenol and TDE; cyclodiene insecticides such as , bromocyclen, chlorbicyclen, , , , dilor, , alpha-endosulfan, , HEOD, , HHDN, , isodrin, kelevan and ; insecticides such as bromfenvinfos, , crotoxyphos, , , dimeth- ylvinphos, fospirate, heptenophos, methocrotophos, , monocrobophos, , naftalofos, , propaphos, TEPP and ; organothiophosphate insecticides such as dioxabenzofos, fosmethilan and 30 ; aliphatic organorhiophosphate insecticides such as acethion, amiton, cadusafos, , chlorme- phos,, demephion-O, demephion- S, , demeton- O, demeton-S, demeton-methyl,demeton- O-methyl, demeton-S-methyl, demeton-S-methylsulphon, , , , IPSP, isothioate, , methacri- fos, oxydemeton-methyl, oxydeprofos, oxydisulfoton, , , and thiometon; aliphatic amide organ- othiophosphate insecticides such as amidithion, cyanthoate, , ethoate-methyl, , mecarbam, ometh- 35 oate, , sophamide and vamidothion; oxime organothiophosphate insecticides such as chlorphoxim, and phoxim-methyl; heterocyclic organothiophosphate insecticides such as , , coumithoate, , , menazon, morphothion, , pyraclofos, pyridaphenthion and quinothion; benzothiopyran organothiophosphate insecticides such as dithicrofos and thicrofos; benzotriazine organothiophosphate insecticides such as azinphos-ethyl and azinphos- methyl; isoindole organothiophosphate insecticides such as dialifos and ; 40 isoxazole organothiophosphate insecticides such asisoxathion and zolaprofos; pyrazolopyrimidine organothiophosphate insecticides such as chlorprazophos and pyrazophos; pyridine organothiophosphate insecticides such as and chlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such as butathiofos, , etrimfos, lirimfos, pirimiphos-ethyl, pirimiphos-methyl, primidophos, pyrimitate and ; quinoxaline organothiophosphate insec- ticides such as and quinalphos-methyl; thiadiazole organothiophosphate insecticides such as athidathion, 45 lythidathion, and prothidathion; triazole organothiophosphate insecticides such as isazofos and triazophos; phenyl organothiophosphate insecticides such as azothoate, bromophos, bromophos-ethyl, , chlorthi- ophos, , cythioate, dicapthon, dichlofenthion, etaphos, famphur, fenchlorphos, fensulfothion, fen- thion, -ethyl, heterophos, jodfenphos, mesulfenfos, , parathion- methyl, phenkapton, phosnichlor, pro- fenofos, prothiofos, sulprofos, temephos, trichlormetaphos- 3 and trifenofos; phosphonate insecticides such as butonate 50 and trichlorfon; phosphonothioate insecticides such as mecarphon; phenyl ethylphosphonothioate insecticides such as and trichloronat; phenyl phenylphosphonothioate insecticides such as cyanofenphos, EPM and ; phos- phoramidate insecticides such as crufomate, , fosthietan, mephosfolan, and pirimetaphos; phos- phoramidothioate insecticides such as , isocarbophos, isofenphos, isofenphos-methyl, and propetamphos; phosphorodiamide insecticides such as , mazidox, and , oxadiazine insecti- 55 cides such as ; oxadiazoline insecticides such as metoxadiazone; phthalimide insecticides such as dialifos, phosmet and ; pyrazole insecticides such as , tolefenpyrad; phenylpyrazole insecticides such as acetoprole, ethiprole, , pyrafluprole, and vaniliprole; ester insecticides such as , allethrin, , barthrin, , bioethanomethrin, cyclethrin, cycloprothrin, , beta-cyfluthrin, cyha-

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lothrin, gamma-, lambda-cyhalothrin, , alpha-cypermethrin, beta-cypermethrin, theta-cyper- methrin, zeta-cypermethrin, , , dimefluthrin, dimethrin, , fenfluthrin, fenpirithrin, fen- propathrin, , , flucythrinate, fluvalinate, tau-fluvalinate, furethrin, , , per- methrin, biopermethrin, transpermethrin, , , profluthrin, pyresmethrin, , bioresmethrin, 5 cismethrin, , terallethrin, tetramethrin, and ; pyrethroid ether insecticides such as etofen- prox, flufenprox, halfenprox, protrifenbute and ; pyrimidinamine insecticides such as flufenerim and pyrimidifen; pyrrole insecticides such as ; tetramic acid insecticides such as spirotetramat; tetronic acid insecticides such as spiromesifen; thiourea insecticides such as diafenthiuron; urea insecticides such as flucofuron and sulcofuron; and unclassified insecticides such as closantel, copper naphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, hydram- 10 ethylnon, isoprothiolane, malonoben, , nifluridide, plifenate, pyridaben, pyridalyl, pyrifluquinazon, rafox- anide, , triarathene and triazamate, and any combinations thereof. [0022] Additionally, the compound of the present disclosure may be combined with herbicides that are compatible with the compound of the present disclosure in the medium selected for application, and not antagonistic to the activity of the present compound to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal compound of the 15 present disclosure may be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants. When used in conjunction with herbicides, 5-fluorocytosine may be formulated with the herbicide(s), tank mixed with the herbicide (s) or applied sequentially with the herbicide (s). Typical herbicides include, but are not limited to: amide herbicides such as allidochlor, beflubutamid, benzadox, benzipram, bromobutide, cafenstrole, CDEA, cyprazole, dimeth- enamid, dimethenamid-P, diphenamid, epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, isocarb- 20 amid, isoxaben, napropamide, naptalam, pethoxamid, propyzamide, quinonamid and tebutam; anilide herbicides such aschloxanocryl, cisanilide,clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinafen and propanil; arylalamine herbicides such as benzoylprop, flampropand flamprop- M; chloroacetanilideherbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, pry- 25 nachlor, terbuchlor, thenylchlor and xylachlor; sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide herbicides such as asulam, carbasulam, fenasulam and oryzalin; thioamide herbicides such as chlorthiamid; antibiotic herbicides such as bilanafos; benzoic acid herbicides such as chloramben, dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid herbicides such as bispyribac and pyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as aminopyralid, 30 clopyralid and picloram; quinolinecarboxylic acid herbicides such as quinclorac and quinmerac;arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite; ben- zoylcyclohexanedione herbicides such as mesotrione, sulcutrione, tefuryltrione and tembotrione; benzofuranyl alkylsul- fonate herbicides such as benfuresate and ethofumesate;benzothiazole herbicides such as benzazolin; carbamate herbicides such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam, karbutilate and terbucarb;carbanilate 35 herbicides such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham-ethyl, propham and swep; cyclohexene oxime herbicides such as al- loxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim;cy- clopropylisoxazole herbicides such as isoxachlortole and isoxaflutole; dicarboximide herbicides such as cinidon-ethyl, flumezin, flumiclorac, flumioxazin and flumipropyn; dinitroaniline herbicides such as benfluralin, butralin, dinitramine, 40 ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and triflu - ralin; dinitrophenolherbicides such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenyl ether herbicides such as acifluorfen, aclonifen, bifenox, chlom- ethoxyfen, chlomitrofen, etnipromid, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such as dazomet and metam; halogenated 45 aliphalic herbicides such as alorac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicides such as imazamethabenz, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr; inorganic herbicides such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, potassium cyanate, sodium azide, sodium chlorate and sulfuric acid;nitrile herbicides such as bromobonil, bromoxynil, chloroxynil, dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorus 50 herbicides such as amiprofos-methyl, anilofos, , bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glu- fosinate, glufosinate-P, glyphosate and piperophos; phenoxy herbicides such as bromofenoxim, clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol and trifopsime; oxadiazoline herbicides such as methazole, oxadiargyl, oxadiazon; oxazole herbicides such as fenoxasulfone; phenoxyacetic herbicides such as 4- CPA, 2,4-D, 3,4- DA, MCPA, MCPA-thioethyl and 2,4,5-T; phenoxybutyric herbicides such as 4-CPB, 2,4-DB, 3,4-DB, MCPB and 2,4,5- 55 TB; phenoxypropionic herbicides such as cloprop, 4- CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop and mecoprop-P; aryloxyphenoxypropionic herbicides such as chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxa- prop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop- P, haloxyfop, haloxyfop- P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P and trifop; phenylenediamine herbicides such as dinitramine and prodiamine; pyrazole herbi-

6 EP 2 317 851 B1

cides such as pyroxasulfone; benzoylpyrazole herbicides such as benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, and topramezone; phenylpyrazole herbicides such as fluazolate, nipyraclofen, pioxaden and pyraflufen; pyridazine her- bicides such as credazine, pyridafol and pyridate; pyridazinone herbicides such as brompyrazon, chloridazon, dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazon and pydanon;pyridine herbicides such as aminopyralid, cliodinate, 5 clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram, picolinafen, pyriclor, thiazopyr and triclopyr;pyrimidinediamine herbicides such as iprymidam and tioclorim; quaternary ammonium herbicides such as cyperquat, diethamquat, difen- zoquat, diquat, morfamquat and paraquat; thiocarbamate herbicides such as butylate, cycloate, di- allate, EPTC, espro- carb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, sulfallate, thioben- carb, tiocarbazil, tri-allate and vernolate; thiocarbonate herbicides such as dimexano, EXD and proxan; thiourea herbi- 10 cides such as methiuron; triazine herbicides such as dipropetryn, indaziflam, triaziflam and trihydroxytriazine; chlorotri- azine herbicides such as atrazine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine and trietazine;methoxytriazine herbicides such as atraton, methometon, prometon, secbumeton, simeton and terbumeton; methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn, simetryn and terbutryn; triazinone her- 15 bicides such as ametridione, amibuzin, hexazinone, isomethiozin, metamitron and metribuzin; triazole herbicides such as amitrole, cafenstrole, epronaz and flupoxam; triazolone herbicides such as amicarbazone, bencarbazone, carfentra- zone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and thiencarbazone-methyl; triazolopyrimidine herbicides such as cloransulam, diclosulam, florasolam, flumetsulam, metosulam, penoxsulam and pyroxsulam; uracil herbicides such as benzfendizone, bromacil, butafenacil, flupropacil, isocil, lenacil, saflufenacil and terbacil;area her- 20 bicides such as benzthiazuron, cumyluron, cycluron, dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthia- zuron, monisouron and noruron; phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chloro- toluron, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, Linuron, methiuron, methyldymron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phe- nobenzuron, siduron, tetrafluron and thidiazuron; pyrimidinylsulfonylurea herbicides such as amidosulfuron, azimsul- 25 furon, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foram- sulfuron, halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, prim- isulfuron, propyrisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron and trifloxysulfuron; triazinylsulfony- lurea herbicides such as chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron, prosulfuron, thifensul- furon, triasulfuron, tribenuron, triflusulfuron and tritosulfuron; thiadiazolylurea herbicides such as buthiuron, ethidimuron, 30 tebuthiuron, thiazafluron and thidiazuron; and unclassifiedherbicides such as acrolein, allyl alcohol,aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon, bicyclopyrone, buthidazole, calcium cyanamide, cambendichlor, chlorfenac, chlo- rfenprop, chlorflurazole, chlorflurenol, cinmethylin, clomazone, CPMF, cresol, cyanamide, ortho- dichlorobenzene, dime- piperate, endothal, fluoromidine, fluridone, flurochloridone, flurtamone, fluthiacet, indanofan, methyl isothiocyanate, OCH, oxaziclomefone, pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin, pyribenzoxim, pyriftalid, 35 quinoclamine, rhodethanil, sulglycapin, thidiazimin, tridiphane, trimetaron, tripropindan and tritac. [0023] One embodiment of the present disclosure is a method for the control or prevention of fungal attack. This method comprises applying to the soil, plant, roots, foliage, seed or locus of the fungus, or to a locus in which the infestation is to be prevented (for example applying to cereal or grape plants), a fungicidally effective amount of 5- fluorocytosine. The compound is suitable for treatment of various plants at fungicidal levels, while exhibiting low phyto- 40 toxicity. The compound may be useful both in a protectant and/or an eradicant fashion. [0024] The compound has been found to have significant fungicidal effect particularly for agricultural use, and is particularly effective for use with agricultural crops and horticultural plants. [0025] It will be understood by those in the art that the efficacy of the compound for the foregoing fungi establishes the general utility of the compound as a fungicide. 45 [0026] The compound has broad ranges of efficacy as a fungicide. The exact amount of the active material to be applied is dependent not only on the specific active material being applied, but also on the particular action desired, the fungal species to be controlled, and the stage of growth thereof, as well as the part of the plant or other product to be contacted with the compound. Thus, the compound, and formulations containing the same, may not be equally effective at similar concentrations or against the same fungal species. ((stet)) 50 [0027] The compound is 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 is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, 55 the particular plant species, climate conditions, and the like. A suitable application rate is typically in the range from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m2). [0028] Any range or desired value given herein may be extended or altered without losing the effects sought, as is apparent to the skilled person for an understanding of the teachings herein.

7 EP 2 317 851 B1

Biological Testing

[0029] For the following examples, 5-fluorocytosine or a 5-fluorocytosine derivative (for comparision) was either dis- solved in acetone or water, and dilutions were performed to obtain desirable rates. The spray solutions contained either 5 0.01% triton X-100 or 0.1% Trycol 5941. For high-volume spray, plants were sprayed to run-off using an automated booth sprayer. For a low-volume test, fungicide was applied using a track sprayer with application volume of 200 liters/ hectare (L/H). [0030] Plants were inoculated with fungal pathogens either 3 days before compound application (3- day curative test; 3DC) or 1 day after compound application (1-day protectant test; 1DP). 10 Examples:

[0031]

15 1. Evaluation of Fungicidal Activity Leaf Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici; Bayer code SEPTTR): Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50% mineral soil/50% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per pot. These plants were inoculated with an aqueous spore suspension of Septoria critici either prior to or after fungicide treatments. After inoculation the plants were 20 kept in 100% relative humidity (one day in a dark dew chamber followed by two to three days in a lighted dew chamber) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse for disease to develop. 2. Evaluation of Fungicidal Activity: Glume Blotch of Wheat Leptosphaeria( nodorum; Bayer code LEPTNO; an- amorph: Stagonospora nodorum); 25 Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50% miniral soil/50% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per pot. Wheat seedlings were inoculated with an aqueous spore suspension of Leptosphaeria nodorum. After inoculation the plants were kept in 100% relative humidity (one day in a dark dew chamber followed by three days in a lighted dew chamber) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse to allow disease to develop. 30 3. Evaluation of Fungicidal Activity: Spot Blotch of Barley ( Cochliobolus sativum; Bayer code COCHSA; anamorph: Helminthosporium sativum): Barley plants (variety Harrington) were grown from seeds in a greenhouse in soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per pot. Plants were inoculated with a spore suspension of Helminthosporium sativum. After inoculation barley seedlings were placed in a dark dew room with 100% relative humidity for a period 35 of 24 hours, and then moved to a greenhouse for disease to develop. 4. Evaluation of Fungicidal Activity: Leaf Spot of Sugar Beets (Cercospora beticola; Bayer code CERCBE): Sugar beets (variety HH-88) were grown in soil-less Metro mix in a greenhouse. The spores were harvested from moisturized infected leaf surface by washing whole leaves in water, and then filtered through two layers of cheese- cloth. The young seedlings were inoculated with the spore suspension, The plants were kept in a dark dew room 40 for 48 hours, and then placed under a plastic hood in a greenhouse with a temperature of 26 °C. 5.Evaluation ofFungicidal Activity: Leaf Spot ofPeanut (Mycosphaerellaarachidis ; Bayercode MYCOAR; anamorph: Cercospora arachidicola); Peanut seedlings (variety Star) were grown in soil-less Metro mix. The spores were harvested from moisturized infected leaf surface by washing whole leaves in water, and then filtered through two layers of cheesecloth. The 45 young seedlings were inoculated with the spore suspension. The plants were kept in a dark dew room for 48 hours, and then placed under a plastic hood in a greenhouse with a temperature of 26 °C. 6. Evaluation of Fungicidal Activity: Cucumber Anthracnose Glomerella( lagenarium; anamorph: Colletotrichum lagenarium; Bayer code COLLLA); Cucumber seedlings (variety Bush Champion) were grown in soil- less Metro mix in a greenhouse. Cucumber plants 50 were inoculated with a spore suspension and maintained in a dark dew room overnight. Plants were then moved to a growth chamber for disease development. 7. Evaluation of Fungicidal Activity: Apple Scab (Venturia inaequalis; Bayer code VENTIN): Apple seedlings (McIntosh or Golden Delicious) were grown in Metro mix in a greenhouse. Fungal spores were collected from infected leaf tissue. Plants were inoculated with the spore suspension. Plants were placed in a dew 55 room for 24 hours with 100% relative humidity and then transferred to a greenhouse with a temperature of 18 °C for disease to develop. 8. Evaluation of fungicidal activity: Black Sigatoka Disease of Banana (Mycosphaerella fijiensis; BAYER code MY- COFI):

8 EP 2 317 851 B1

Efficacy against Mycosphaerella fijiensis was tested using newly emerged leaves of field grown banana plants. 20 mL of a diluted formulation of 5-fluorocytosine of the required concentration were sprayed onto each test leaf over a delineated area of 20 x 20 cm. The leaves were subsequently allowed to become infected by natural inoculum, and were visually assessed for percent disease Control ∼ 40 - 45 days later. 5 [0032] The following tables present the activity of 5-fluorocytosine (Table I) or a 5-fluorocytosine derivative (Table II) when evaluated in these experiments. The effectiveness of 5- fluorocytosine or 5-fluorocytosine derivative in controlling disease was determined by assessing the severity of disease on treated plants, then converting the severity to percent control based on the level of disease on untreated, inoculated plants. 10 [0033] Tn each case of Tables I and II the rating scale is as follows:

% Disease Control Rating 76-100 A 15 51-75 B 26-50 C 0-25 D Not tested E 20

Table I: Activity of 5-Fluorocytosine against Plant Diseases % Disease Control of % Disease Control of Entry Number Pathogen Rate, ppm, 1DP Rate, ppm, 3DC 25 5-FC 5-FC 1 COCHSA 200 C 200 E 2 COLLLA 200 A 200 E

30 3 SEPTTR 200 A 100 A 4 MYCOAR 100 A 100 A 5 CERCBE 100 A 100 E 6 LEPTNO 100 D 100 C 35 7 VENTIN 75 A 75 A 8 MYCOFI 200 B 100 B

40 Table II: One-Day Protectant (1DP) and Three-Day Curative (3DC) Activity of Compounds on SEPTTR at 100 ppm (for comparison) Cmpd Structure SEPTTR 100 PPM 1DP SEPTTR 100 PPM 3DC

45 2AA

50 3AA

55 4AA

9 EP 2 317 851 B1

(continued) Cmpd Structure SEPTTR 100 PPM 1DP SEPTTR 100 PPM 3DC

5 5AB

10 6AC

7BB 15

8AA

20

9AC

25

10 C D

30

11 A A

35

12 A A

40

13 A A

45

14 c D

50

15 A B

55 16 A A

10 EP 2 317 851 B1

(continued) Cmpd Structure SEPTTR 100 PPM 1DP SEPTTR 100 PPM 3DC

5 17 C A

10 18 D B

19 D D 15

20 D D

20

21 D D

25

22 D D

30

23 C D

35

24 C C

40

Claims

1. A method of controlling a pathogen-induced disease in a plant that is at risk of being diseased from the pathogen 45 comprising contacting one of the plant and an area adjacent to the plant with 5- fluorocytosine, wherein the disease isone of apple scab, speckled leaf blotch of wheat,leaf spot of sugarbeets, leaf spot of peanut, cucumberanthracnose, and black sigatoka.

2. The method of claim 1 wherein the composition further comprises an . 50 3. The method of claim 1 wherein the composition further comprises a weed control agent.

Patentansprüche 55 1. Verfahren zur Bekämpfung einer Pathogen-induzierten Erkrankung in einer Pflanze, welche gefährdet ist an dem Pathogen zu erkranken, umfassend inkontaktbringen einer der Pflanzen und/oder der Pflanzenumgebung mit 5-

11 EP 2 317 851 B1

Fluorcytosin, wobei die Erkrankung eine von Apfelschorf, Blattdürre (speckled leaf blotch) von Weizen, Blattflek- kenkrankheit (leaf spot) von Zuckerrüben, Blattfleckenkrankheit von Erdnüssen, Gurkenanthracnose, und schwarzer Sigatoka ist.

5 2. Verfahren nach Anspruch 1, wobei die Zusammensetzung weiterhin ein Insektizid umfasst.

3. Verfahren nach Anspruch 1, wobei die Zusammensetzung weiterhin ein Unkrautbekämpfungsmittel umfasst.

10 Revendications

1. Procédé de lutte contre une maladie provoquée par un agent pathogène chez un végétal qui risque d’être rendu malade par l’agent pathogène, lequel procédé comporte le fait de mettre le végétal, ou une zone adjacente au végétal, en contact avec de la 5-fluoro-cytosine, étant entendu que la maladie est l’une des suivantes : tavelure du 15 pommier, septoriose du blé, cercosporiose de la betterave sucrière, cercosporiose de l’arachide, anthracnose des cucurbitacées, et cercosporiose du bananier.

2. Procédé conforme à la revendication 1, dans lequel la composition comprend en outre un insecticide.

20 3. Procédé conforme à la revendication 1, dans lequel la composition comprend en outre un agent de lutte contre les mauvaises herbes.

25

30

35

40

45

50

55

12 EP 2 317 851 B1

REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• US 3368938 A [0005] • WO 2009071726 A1, Bautista Rodriguez, J. [0007] • US 3309359 A, Duschinsky, R, and Hoffer, M. [0007] • US 495228 A [0018] • WO 2005080351 A1, Li, J. [0007]

Non-patent literature cited in the description

• DUSCHINSKY, R. J. Med Chem., 1966, vol. 9, 566-572 [0007]

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