HUE034376T2

Synergistic fungicidial mixtures for fungal control in cereals

Abstract

This record has no abstract on file.

HUE034376T2, drawing sheet 1 — Sheet 1 of 4

Term

No projected expiry on record.

9 claims: 1 independent, 8 dependent

1
Claims 1. A synergistic fungicidal mixture comprising a fungicidally effective amount of a compound of Formula l-V and at least one fungicide selected from the group consisting of azoxystrobin and pyraclostrobin,
2
The mixture of Claim 1 in which the weight ratio of Compound l-V to azoxystrobin is between 1:10 and 10:1.
3
The mixture of Claim 1 in which the weight ratio of Compound l-V to pyraclostrobin is between 1:10 and 10:1.
4
A fungicidal composition comprising a fungicidally effective amount of the fungicidal mixture of Claim 1 and an agriculturally acceptable adjuvant or carrier.

Independent claims4

125 paragraphs, as filed

(56) References cited:

• ANONYMOUS: Synergistic Fungicidal Compositions of Heterocyclic Aromatic Amides and Triazoles, IP.COM JOURNAL, IP.COM INC., WEST HENRIETTA, NY, US, 20 July 2004 (2004-07-20), XP013020905, ISSN: 1533-0001 • Disclosed Anonymously: Fungicidal Mixtures, IP.com Prior Art Database Technical Disclosure, 5 July 2005 (2005-07-05), pages 1-10, XP055073888, DÓI:

http://ip.com/pdf/ipcompad/IPCOM000126160D . pdf Retrieved from the Internet: URL:http://priorart.ip.com/IPCOM/000126160 [retrieved on 2013-08-01]

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Note: Within nine months ofthe publication ofthe mention ofthe grant ofthe 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 nőt be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).

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Description

Field of the Invention [0001] This invention concerns a synergistic fungicidal composition containing (a) a compound of Formula I, II, lll, IV or V and (b) at least one fungicide selected from the group consisting of azoxystrobin and pyraclostrobin.

Background ofthe Invention [0002] Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, somé crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield and the quality ofthe crop, and consequently, increase the value ofthe crop. In most situations, the increase in value ofthe crop is worth at least three times the cost of the use of the fungicide.

[0003] However, no one fungicide is useful in all situations and repeated usage of a single fungicide frequently leads to the development of resistance to that and related fungicides. Consequently, research is being conducted to produce fungicides and combinations of fungicides that are safer, that have better performance, that require lower dosages, that are easier to use, and that cost less.

[0004] Synergism occurs when the activity of two or more compounds exceeds the activities of the compounds when used alone. Synergistic mixtures of picolinamides and a second compound selected from, among others, epoxiconazole are described in an anonymous contribution entitled Synergistic Fungicidal Compositions of Heterocyclic Aromatic Amides and Triazoles, published on IP.COM on July 20, 2004.

[0005] Fungicidal mixtures of picolinamides and a second compound selected from, among others, azoxystrobin, are described in an anonymous contribution entitled Fungicidal Mixtures, published on IP.COM on July 05, 2005.

Summary ofthe Invention [0006] It is an object of this invention to provide synergistic compositions comprising fungicidal compounds. It is a further object of this invention to provide processes that use these synergistic compositions. The synergistic compositions are capable of preventing or curing, or both, diseases caused by fungi ofthe classes Ascomycetes and Basidiomycetes. In addition, the synergistic compositions have improved efficacy against the Ascomycete and Basidiomycete pathogens, including leaf blotch and brown rust ofwheat. In accordance with this invention, synergistic compositions are provided along with methods fór their use.

Detailed Description ofthe Invention [0007] The present invention concerns a synergistic fungicidal mixture comprising an fungicidally effective amount of (a) a compound of Formula I, II, lll, IV orV, and (b) at least one fungicide selected from the group consisting of azoxystrobin and pyraclostrobin.

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V [0008] Azoxystrobin is the common name tor methyl (aE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a-(methoxymethylene)benzeneacetate. Itsfungicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Azoxystrobin Controls a variety of pathogens at application rates between 100 and 375 grams/hectare (g/ha).

[0009] Pyraclostrobin is the common name tor methyl [2-[[[1-(4-chlorophenyl)-1/-/-pyrazol-3-yl]oxy]methyl]phenyl]methoxycarbamate. Itsfungicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Pyraclostrobin Controls major plánt pathogens, such as Septoria tritici, Puccinia spp., Drechslera tritici-repentis and Pyrenophora teres in cereals.

[0010] In the composition of this invention, the weight ratio ofthe compounds of Formula l-V to azoxystrobin at which the fungicidal effect is synergistic lies within the rangé of between about 1:10 and about 10:1. The weight ratio ofthe compounds of Formula l-V to pyraclostrobin at which the fungicidal effect is synergistic lies within the rangé of between about 1:10 and about 10:1.

[0011] The rate at which the synergistic composition is applied will depend upon the particular type of fungus to be controlled, the degree of control required and the timing and method of application. In generál, the composition ofthe invention can be applied at an application rate of between about 65 grams per hectare (g/ha) and about 2300 g/ha based on the totál amount of active ingredients in the composition. Azoxystrobin is applied at a rate between about 50 g/ha and about 250 g/ha and the compound of Formula l-V is applied at a rate between about 35 g/ha and about 300 g/ha. Pyraclostrobin is applied at a rate between about 50 g/ha and about 250 g/ha and the compound of Formula l-V is applied at a rate between about 35 g/ha and about 300 g/ha.

[0012] The components ofthe synergistic mixture ofthe present invention can be applied either separately or as part of a multipart fungicidal system.

[0013] The synergistic mixture ofthe present invention can be applied in conjunction with one or more otherfungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), the presently claimed compounds may be formulated with the other fungicide(s), tank mixed with the other fungicide(s) or applied sequentially with the otherfungicide(s). Such otherfungicides may include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzenesulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodinefree base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutri4

ΕΡ 2 904 901 Β1 afol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoximmethyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuricchloride, mercuricoxide, mercurous chloride, metalaxyl, metalaxyl-M, métám, metam-ammonium, metampotassium, metam-sodium, metconazole, methasulfocarb, methyi iodide, methyi isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonicacid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (RS)-/V-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop1-enyl)phenyl thiocyanateme, ampropylfos, anilazine, azithiram, bárium polysulfide, Bayer32394, benodanil, benquinox, bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copperzinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copperzinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, /V-3,5-dichlorophenyl-succinimide, /V-3-nitrophenylitaconimide, natamycin, /V-ethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitráté, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, zarilamid, and any combinations thereof.

[0014] The compositions of the present invention are preferably applied in the form of a formulation comprising a composition of (a) a compound of Formula I and (b) at least one fungicide selected from the group consisting of azoxystrobin and pyraclostrobin, together with a phytologically acceptable carrier.

[0015] Concentrated formulations can be dispersed in water, or another liquid, for application, or formulations can be dust-like or granular, which can then be applied without further treatment. The formulations are prepared according to procedures which are conventional in the agricultural Chemical art, bút which are növel and important because ofthe presence therein of a synergistic composition.

[0016] The formulations that are applied most often are aqueous suspensions or emulsions. Either such water-soluble, water-suspendable, oremulsifiable formulations are solids, usually known as wettable powders, or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. The present invention contemplates all vehicles by which the synergistic compositions can be formulated for delivery and use as a fungicide.

[0017] As will be readily appreciated, any matéria! to which these synergistic compositions can be added may be used, provided they yield the desired utility without significant interference with the activity of these synergistic compositions as antifungal agents.

[0018] Wettable powders, which may be compacted toform water-dispersible granules, comprise an intimate mixture ofthe synergistic composition, a carrier and agriculturally acceptable surfactants. The concentration ofthe synergistic composition in the wettable powder is usually from about 10% to about 90% by weight, more preferably about 25% to about 75% by weight, based on the totál weight ofthe formulation. In the preparation of wettable powder formulations, the synergistic composition can be compounded with any of the finely divided solids, such as prophyllite, talc, chalk, gypsum, Fuller’s earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified

ΕΡ 2 904 901 Β1 silicates or the like. In such operations, the finely divided carrier is ground or mixed with the synergistic composition in a volatile organic solvent. Effective surfactants, comprising from about 0.5% to about 10% by weight of the wettable powder, include sulfonated lignins, naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants, such as ethylene oxide adducts of alkyl phenols.

[0019] Emulsifiable concentrates ofthe synergistic composition comprise a convenient concentration, such as from about 10% to about 50% by weight, in a suitable liquid, based on the totál weight of the emulsifiable concentrate formulation. The components ofthe synergistic compositions, jointly or separately, are dissolved in a 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 petróleum such as heavy aromatic naphtha. Other organic solvents may alsó be used, such as, fór example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.

[0020] Emulsifiers which can be advantageously employed herein can 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 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 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 phosphated polyglycol ether.

[0021] Representative organic liquids which can be employed in preparing the emulsifiable concentrates ofthe 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 or methyl ether of diethylene glycol, and the methyl ether of triethylene glycol. Mixtures of two or more organic liquids are alsó often suitably employed in the preparation ofthe emulsifiable concentrate. The preferred organic liquids are xylene, and propyl benzene fractions, with xylene being most preferred. The surface-active dispersing agents are usually employed in liquid formulations and in the amount of from 0.1 to 20 percent by weight of the combined weight of the dispersing agent with the synergistic compositions. The formulations can alsó contain other compatible additives, fór example, plánt growth regulators and other biologically active compounds used in agriculture.

[0022] Aqueous suspensions comprise suspensions of one or more water-insoluble compounds, dispersed in an aqueous vehicle at a concentration in the rangé from about 5% to about 70% by weight, based on the totál weight of the aqueous suspension formulation. Suspensions are prepared by finely grinding the components of the synergistic combination either together or separately, and vigorously mixing the ground matériái intő a vehicle comprised of water and surfactants chosen from the same types discussed above. Other ingredients, such as inorganic salts and synthetic or natural gums, may alsó be added to increase the density and viscosity ofthe aqueous vehicle. It is often most effective to grind and mix at the same time by preparing the aqueous mixture and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.

[0023] The synergistic composition may alsó be applied as a granular formulation, which is particularly useful fór applications to the soil. Granular formulations usually contain from about 0.5% to about 10% by weight ofthe compounds, based on the totál weight of the granular formulation, dispersed in a carrier which consists entirely or in large part of coarsely divided attapulgite, bentonite, diatomite, clay or a similar inexpensive substance. Such formulations are usually prepared by dissolving the synergistic composition in a suitable solvent and applying it to a granular carrier which has been preformed to the appropriate partiele size, in the rangé of from about 0.5 to about 3 mm. Such formulations may alsó be prepared by making a dough or pásté ofthe carrier and the synergistic composition, and crushing and drying to obtain the desired granular partidé.

[0024] Dusts containing the synergistic composition are prepared simply by intimately mixing the synergistic composition in powdered form with a suitable dusty agricultural carrier, such as, fór example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1% to about 10% by weight of the synergistic composition/carrier combination.

[0025] The formulations may contain agriculturally acceptable adjuvant surfactants to enhance deposition, wetting and penetration of the synergistic composition onto the target crop and organism. These adjuvant surfactants may optionally be employed as a component ofthe formulation or as a tank mix. The amount of adjuvant surfactant will vary from 0.01 percent to 1.0 percent volume/volume (v/v) based on a spray-volume of water, preferably 0.05 to 0.5 percent. Suitable adjuvant surfactants include ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts ofthe esters orsulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils.

[0026] The formulations may optionally include combinations that can comprise at least 1 % by weight ofone or more

ΕΡ 2 904 901 Β1 ofthe synergistic compositions with another pesticidal compound. Such additional pesticidal compounds may befungicides, insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the synergistic compositions ofthe present invention in the médium selected fór application, and nőt antagonistic to the activity ofthe present compounds. Accordingly, in such embodiments the other pesticidal compound is employed as a supplemental toxicant fór the same or fór a different pesticidal use. The pesticidal compound and the synergistic composition can generally be mixed together in a weight ratio offrom 1:100 to 100:1.

[0027] The present invention includes within its scope methods fór the control or prevention of fungal attack. These methods comprise applying to the locus of the fungus, or to a locus in which the infestation is to be prevented (fór example applying to wheat orbarley plants), a fungicidally effective amount ofthe synergistic corn position. The synergistic composition is suitable fór treatment ofvarious plants atfungicidal levels, while exhibiting lowphytotoxicity. The synergistic composition is useful in a protectant or eradicant fashion. The synergistic composition is applied by any of a variety of known techniques, either as the synergistic composition or as a formulation comprising the synergistic composition. Fór example, the synergistic compositions may be applied to the roots, seeds or foliage of plants fór the control ofvarious fungi, without damaging the commercial value of the plants. The synergistic composition is applied in the form of any of the generally used formulation types, fór example, as Solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates. These materials are conveniently applied in various known fashions.

[0028] The synergistic composition has been found to have significant fungicidal effect, particularly fór agricultural use. The synergistic composition is particularly effective fór use with agricultural crops and horticultural plants, or with wood, paint, leather or carpet backing.

[0029] In particular, the synergistic composition is effective in controlling a variety of undesirable fungi that infect useful plánt crops. The synergistic composition may be used against a variety of Ascomycete and Basidiomycetefungi, including fór example the following representative fungi species: wheat brown rust (Puccinia recondita; Bayer code PUCCRT); stripe rust of wheat (Puccinia striiformis', Bayer code PUCCST); leaf blotch of wheat (Mycosphaerella graminicola', anamorph: Septoria triticr, Bayer code SEPTTR); glume blotch of wheat (Leptosphaeria nodorunr, Bayer code LEPTNO; anamorph: Stagonospora nodorum); spot blotch of barley (Cochliobolus sativunr, Bayer code COCHSA; anamorph: Helminthosporium sativum); leaf spot of sugár beets (Cercospora beticola; Bayer code CERCBE); leaf spot of peanut (Mycosphaerella arachidis; Bayer code MYCOAR; anamorph: Cercospora arachidicola); cucumber anthracnose (Glomerella lagenariunr, anamorph: Colletotrichum lagenarium; Bayer code COLLLA) and black sigatoka disease of banana (Mycosphaerella fijiensis; BAYER code MYCOFI). Itwill be understood by those in the art that the efficacy ofthe synergistic compositions fór one or more of the foregoing fungi establishes the generál utility of the synergistic compositions as fungicides.

[0030] The synergistic compositions have a broad rangé of efficacy as a fungicide. The exact amount ofthe synergistic composition to be applied is dependent nőt only on the relatíve amounts of the components, bút alsó on the particular action desired, the fungal species to be controiied, and the stage of growth thereof, as well as the part of the plánt or other product to be contacted with the synergistic composition. Thus, formulations containing the synergistic composition may nőt be equally effective at similar concentrations or against the same fungal species.

[0031] The synergistic compositions are effective in use with plants in adisease-inhibiting and phytologically acceptable amount. The term disease-inhibiting and phytologically acceptable amount refers to an amount of the synergistic composition that kills or inhibits the plánt disease fór which control is desired, bút is nőt significantly toxic to the plánt. The exact concentration of synergistic composition required varies with the fungal disease to be controiied, the type of formulation employed, the method of application, the particular plánt species, climate conditions, and the Iike.

[0032] The present compositions can be applied to fungi or their locus by the use of conventional ground sprayers, granule applicators, and by other conventional means known to those skilled in the art.

[0033] The following examples are provided to further illustrate the invention.

Examples

Evaluation of Curative and Protectant Activity of Fungicide Mixtures vs. Leaf Blotch of Wheat (Mycosphaerella graminicola', anamorph: Septoria triticr, Bayer code: SEPTTR) [0034] Wheat plants (variety Yuma) were grown from seed in a greenhouse in plastic pots with a surface area of 27.5 square centimeters (cm<sup>2</sup>) containing 50% mineral soil/50% soil-less Metró mix, with 8-12 seedlings per pót. The plants were employed fór testing when first leaf was fully emerged, which typically took 7 to 8 days after planting. Test plants were inoculated with an aqueous spore suspension of Septoria tritici either 3 days prior to (3-day curative test) or 1 day after fungicide treatments (1-day protectant test). After inoculation the plants were kept in 100% relatíve humidity (one day in a dark dew chamber followed by two days in a lighted mist chamber) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse fór disease to develop.

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Evaluation of Curative Activity of Fungicide Mixtures vs. Wheat Brown Rust (Puccinia recondita', Bayer code: PUCCRT) [0035] Yuma wheat seedlings were grown as described above, and inoculated with an aqueous spore suspension of Puccinia recondita 3 days prior to or 1-day after fungicide treatment. After inoculation, plants were kept in 100% relatíve humidity fór 24 hours in a darkdew room to allow spores to germinate and infect plants. The plants were then transferred to a greenhouse fór disease to develop.

[0036] Treatments consisted of fungicides compound I, II, III, IV, V, azoxystrobin and pyraclostrobin, either using Índividuaíly or as two-way mixture with compounds l-V. Technical grades of materials were dissolved in acetone to make stock Solutions, which were then used to perform dilutions in acetone either fór each individual fungicide component or fór the two-way mixture. Desired fungicide rates were obtained after mixing dilutions with 9 volumes of water containing 110 parts per millión (ppm) Triton X-100. Twenty milliliter (mL) fungicide Solutions were applied onto 12 pots of plants using an automated booth sprayer, which utilized two 6218-1/4 JAUPM spray nozzles operating at 20 pounds per square inch (psi) set at opposing angles to cover both leaf surfaces. All sprayed plants were allowed to air dry prior to further handling. Control plants were sprayed in the same manner with the solvent blank.

[0037] When disease fully developed on the control plants, infection levels were assessed on treated plants visually and scored on a scale of 0 to 100 percent. Percentage of disease control was then calculated using the ratio of disease on treated plants relatíve to control plants.

[0038] Colby’s equation was used to determine the fungicidal effects expected from the mixtures. (See Colby, S. R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20-22.) [0039] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected = A + B - (A χ B/100)

A = observed efficacy of active component A at the same concentration as used in the mixture;

B = observed efficacy of active component B at the same concentration as used in the mixture.

[0040] Representative synergistic interactions are presented in the following Tables 1-12.

%DC Obs= Percent disease control observed %DC Exp= Percent disease control expected

Synergism factor = %DC Obs/%DC Exp

Table 1: Synergistic interactions of compound I and other fungicides in 3-day curative (3DC) Septoria tritici (SEPTTR) tests