MXPA98000306A - Fungicide mixtures - Google Patents

Abstract

The present invention describes advantageous combinations of an oxazolidinone and cymoxanil (or their salts suitable from the agricultural point of view) and their use to control fungal diseases in plants, oxazolidinone has the formula (

Description

FUNGICIDAL MIXTURES BACKGROUND OF THE INVENTION This invention relates to agriculturally suitable compositions, which contain an advantageous combination of certain fungicidal oxazolidinone compounds with another fungicide, and methods for the use of such compositions to control fungal diseases in certain plants . The fungicides that effectively control plant diseases are in constant demand by growers. Plant diseases are highly destructive, difficult to control and quickly develop resistance to commercial fungicides. Pesticide combinations are frequently used to facilitate control of the disease, to extend the control spectrum and to retard the development of resistance. It is recognized in the art that the advantages of particular combinations of pesticides can vary frequently, depending on factors such as the particular plant and disease of the plant to be treated, and the treatment conditions. WO 90/12791 describes certain oxazolidinone compounds as fungicides, including 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone (i.e.

REF: 26323 compound of Formula I defined herein). U.S. 3,954,992 describes cymoxanil as a fungicide. Synergistic combinations of cymoxanil and oxazolidenyl acetamides such as oxadixyl are described in U.S. 4,507,310. These references neither describe nor suggest synergistic compositions comprising an oxazolidinone and cymoxanil. BRIEF DESCRIPTION OF THE INVENTION This invention relates to the advantageous combination of cymoxanil (and / or an agriculturally suitable salt thereof) and the oxazolidinone of Formula I. This invention provides compositions which are fungicidally active. comprise a fungicidally effective amount of a mixture of (a) at least one compound selected from the oxazolidinone of Formula I and agriculturally suitable salts thereof and (b) at least one compound selected from cymoJtanil and the agriculturally suitable salts thereof, and optionally (c) at least one of a surfactant, a "solid diluent or a liquid diluent, wherein the weight ratio of the component (a) to the component (b) it is from about 17: 1 to about 1: 100.

The compound of Formula I is also known as 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone. This invention also provides methods for controlling plant diseases caused by plant fungal pathogens, which comprises applying to the plant or portion thereof that is to be protected, or to the seed of the plant or seedling to be protected one of the following : 1) an effective amount * of fungicidal composition comprising (a) the compound of Formula I defined above, or an agriculturally suitable salt thereof, (b) cymoxanil, or a suitable salt from the point of view of the same, and (c) at least one of a surfactant, a solid diluent or a liquid diluent; 2) (i) an effective amount of a first composition comprising (a) the compound of Formula I defined above, or a suitable salt from the agricultural point of view thereof, and (cl) at least one of a surfactant, a solid or liquid diluent; and (ii) an effective amount of a second composition comprising (b) cymoxanil or an agriculturally suitable salt thereof, and (c2) at least one of a surfactant, a solid diluent or a liquid diluent; the first and second compositions sequentially applied in any order; or 3) an effective amount of a physical mixture of the first and second compositions defined in 2 above. The weight ratio of the compound of (a) to the compound of (b) applied is usually from about 17: 1 to 1: 100, and the compound of (a) and the compound of (b) are usually applied in effective amounts to provide control of the fungal disease which is greater than the additive control "of the fungal disease provided by the compound (a) and the compound (b) individually.

DETAILED DESCRIPTION OF THE INVENTION It has been found that combinations of the Formula I and cymoxanil provide control of certain plant diseases which is substantially and surprisingly improved over the expected simply additive control by the components. Cymoxanil, commercially known as Curzate®, is a commercially available foliar fungicide for the control of late blight and powdery mildew diseases, particularly for the systemic and corrective control of late potato wilt and powdery mildew. the grape, which has the formula? which is also known as 2-cyano-N- [(ethylamino) -carbonyl] -2- (methoxyimino) acetamide. The compound of Formula I can exist as enantiomers. One skilled in the art will appreciate that one enantiomer may be more active and / or may exhibit beneficial effects when enriched relative to the other enantiomer, or when it is separated from the other enantiomer. Additionally, the skilled artisan knows how to selectively separate, enrich, and / or prepare the enantiomers. Accordingly, the present invention comprises compositions of the individual enantiomers or optically active mixtures of the oxazolidinone of Formula I, as well as the agriculturally suitable salts thereof in admixture with cymoxanil or a suitable salt from the point of view of agricultural view of it.

The cymoxanil can be prepared by the procedures described in U.S. 3,954,992. The preparation of the compositions of the present invention containing cymoxanil and the compound of Formula I is discussed later in the application. The compound of Formula I can be prepared as described in Scheme 1 and is described in WO 94. / 11359.

Scheme 1 wherein: R6 is alkyl of 1 to 4 carbon atoms; and Y is 1-imidazolyl or 1,2,4-triazolyl. Suitable reaction conditions for preparing the compound of Formula I are as follows. For the conversion of the esters of Formula II to compounds of Formula IV, suitable solvents include inert organic solvents. Preferred solvents are methylene chloride, chloroform, carbon tetrachloride, hexanes, tetrahydrofuran, tert-butylmethyl ether, dioxanes, chlorobenzene, o-dichlorobenzene (ODCB), toluene, xylenes, and suitable combinations thereof. The most preferred solvents are selected from the group consisting of chlorobenzene, ODCB, toluene and xylenes. The reaction temperatures may be in the range from about 10 ° C to about 75 ° C. Preferred temperatures are from about 40 ° C to about 60 ° C. Suitable reaction pressures are from about 1.0 x 105 to about 5.1 x 10 5 Pascals. The preferred pressure is 1 x 105 Pascals. Reaction times are typically 1 to 24 hours, preferably 3 to 6 hours. A suitable ratio of Formula III to II is from about 1: 1 to 2: 1. The preferred ratio is from about 1.1: 1 to 1.8: 1. Suitable bases for this reaction include trialkylamines, imidazole, pyridine, picolines or other substituted pyridine derivatives. For the conversion of the compounds of Formula IV to the 2,4-oxazolidinedione of Formula I, suitable solvents are as noted above for the condensation of Formulas II and III. Preferred solvents are those described above as preferred. The reaction temperatures are from about 0 ° C to about 75 ° C. The preferred temperatures are from about 10 ° C to about 50 ° C. The reaction pressures are from about 1.0 x 105 to about 5.1 to 105 Pascal. The preferred pressure is 1 x 105 Pascals. Reaction times are typically 1 to 24 hours, preferably 2 to 6 hours hours. Suitable acids to catalyze the reaction are selected from the group consisting of alkyl and aryl carboxylic acids, trialkylammonium halides and combinations thereof. The preferred acids are acetic acid and triethylammonium chloride. The most preferred acid is triethylammonium chloride. Suitable ratios of phenylhydrazine to Formula IV is from about 2: 1 to 1: 1. The preferred ratio is from about 1.6: 1 to 1.1: 1. The carbonylation agent of Formula III can be added as a pure compound, a solution of the pure compound in an inert solvent, or prepared in itself in the presence of an ester of Formula II. The preferred process involves the preparation of the carbonylating agent in itself. The methods for preparing the compounds of Formula III, including methods in itself, from phosgene [or phosgene equivalents such as diphosgene (trichloromethyl chloroformate) or triphosgene [bis (trichloromethyl) carbonate)] and either imidazole or triazole are known in the art (see Org. Sintheses, Coil, Vol. 5,201, (1973)). The reactions where HCl is released require a base to trap the acid. A suitable base is a trialkylamine or imidazole, or combinations thereof. The preferred base is triethylamine. 1,1'-carbonyldithriazole (Formula III where Y = 1,2,4- triazolyl) can also be prepared by treating an alkali metal salt of triazole, preferably the potassium salt, with phosgene (or one equivalent of phosgene) in a solvent. Preferably, phase transfer catalysts are added to the reactions wherein the triazole salt has a low solubility in the solvent. For example, phase transfer catalyst is preferred when xylene or toluene is used. Any phase transfer catalyst known to a person skilled in the art is suitable. Preferred are tetraaligammonium halides. The triazole salt is prepared by treating the triazole with a suitable base, such as sodium hydroxide or sodium ethoxide. The preferred relative amount of base of alkali metal to triazole to phosgene is 0.5: 1.0: 0.6. The base is also necessary to catalyze the condensation of Formulas II and III. As previously stated, suitable base catalysts are the trialkylamines, imidazole, pyridine, picolines or other substituted pyridines. When 1,1'-carbonyldiimidazole (Formula III wherein Y = 1-imidazolyl) is used, the imidazole that is released with the reaction with Formula II serves as the catalyst. When 1, 1 '-carbonylditriazole is used, the preferred base is pyridine, a picoline, or a mixture of picolina isomers.

The compounds of Formula IV can be isolated and purified, or treated in-house with phenylhydrazine and acid to form the 2,4-oxazolidinedione of Formula I. The preferred method involves the treatment of Formula IV in itself with phenylhydrazine. After the formation of the carbamate of Formula IV is complete, the excess carbonylating agent can be decomposed by the addition of water. The 2-hydroxycarboxylic acid esters of Formula II can be prepared by a number of methods known in the literature: (1) They can be formed from the corresponding 2-hydroxycarboxylic acids by esterification, as is well known in the literature. The 2-hydroxycarboxylic acids can be prepared from methylketones by the formation of cyanohydrins, then hydrolysis, as is also known. For example, Org. Syntheses. Coil. Vol. 4, 58 (1968) teaches the preparation of at-.-Lactic acid from acetophenone. (2) The esters can also be synthesized from ketone cyanohydrin by treatment with alcohols in the presence of HCl, to provide the iminoether hydrochlorides, followed by hydrolysis. (3) A third known method for preparing 2-hydroxycarboxylic acids and esters involves treating 2-keto- acids or 2-keto-esters with nucleophilic organometallic reagents such as Grignard reagents, and alkyl- and aryl-lithium reagents. For example, R.G. Solomon et al., Teaches the preparation of some esters Formula II by the addition of aryl-Grignard reagents to pyruvate esters (J. Org. Chem. (1982), 47, 4692). Similarly, some 2-hydroxycarboxylic acids can be prepared by the regioselective nucleophilic addition of an aryl organometallic reagent to the metal salt (eg, sodium salt) of the pyruvic acid. (4) Another method described in the literature to prepare some 2-aryl-2-hydroxyesters and acids is by acylation of aromatic rings with activated carbonyl compounds e? presence of a protic or Lewis acid. The aromatic substrates capable of undergoing reactions of this type are benzene, diphenyl ether, and other aromatic compounds known to be sufficiently reactive to undergo Friedel-Crafts-type reactions. In the case of mono-substituted benzene derivatives, the acylation preferably occurs, but not necessarily exclusively, at the point of attachment of the substituent. For example, see Org. Syntheses, Coil. Vol. 3,326, (1955), Solomon et al., J. Org. Chem., (1982), 47, 4692 and U.S. 4,922,010.

Carbonyl compounds known to undergo this reaction include pyruvate esters and acids, esters of glyoxylate and acids, and diesters of oxqmalonates. The acids used in the acylation reaction can be either protic in nature, for example, a mixture of acetic and sulfuric acid, or a Lewis acid such as aluminum chloride, tin tetrachloride, titanium tetrachloride, or other acids of Lewis that is known to perform Friedel-Crafts type reactions. The acid can be used either catalytically or in excess. In some cases, the acid may destructively react with the carbonyl substrate and an excess of carbonyl compound must be used. Fungicides that effectively control fungal diseases, particularly of the Oomycetes class, such as Phytophthora spp, and Plasmopara spp, are in constant demand by growers. Fungicide combinations are often used to facilitate disease control and to delay the development of resistance. Mixtures of fungicides can provide significantly better disease control than could be predicted based on the activity of the individual components. This synergism has been described as "the action cooperative of two components of a mixture, such that the total effect is greater or longer than the sum of the effects of the two (or more) taken independently "(see Tames, PML, Neth, J. Plant Pa thology, (1964 ), 70, 73-80) It has been found that compositions containing the compound of Formula I and cymoxanil exhibit synergistic effects.The presence of a synergistic effect between two active ingredients is established with the help of the Colby equation (see Colby, SR In Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds, (1967), 15-20-22): p = A + B - [(A x B) / 100] Using the methods of Colby, the presence of a synergistic interaction between two active ingredients is established by first calculating the predicted activity, p, of the mixture based on activities of the two components applied individually. If p is less than the experimentally established effect, a synergism has occurred. In the above equation, A is the fungicidal activity in the percentage control of a component applied individually in the proportion x. The term B is the fungicidal activity in the percentage control of the second component applied in the proportion Y. The equation estimates p, the fungicidal activity of the mixture of A in the proportion x with B in the proportion and if its effects are strictly additive and no interaction has occurred . In this invention, the fungicidal activities provided by the compositions of Formula I and cymoxanil are individually compared to those of a composition of a compound of Formula I and cymoxanil. Based on the description of synergism developed by Colby, the compositions of the present invention are considered as synergistically useful. More particularly, the compositions comprise (a) at least one compound selected from 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone and its salts suitable from the agricultural point of view, (b) at least one compound selected from 2-cyano-N- [(ethylamino) carbonyl] -2- (methoxy-imino) asetamide and its agriculturally suitable salts, and (c) at least one of a surfactant, a solid diluent or a liquid diluent, where the weight ratio of component (a) and component (b) is between about 17: 1 and about 1: 100, can be synergistic. On the other hand, the compositions comprising the components (a) and (b) individually can be conveniently mixed with an optional diluent before applying it to the crop that is going to be protected. The weight ratio of component (a) to component (b) is preferably from about 8: 1 to about 1:25; and is more preferably from about 4: 1 to about 1:10. Notable are the compositions wherein the weight ratio of component (a) to component (b) is from about 3: 2 to about 1: 3. Accordingly, this invention provides an improved method for combating fungi, particularly fungi of the Oomycetes classes such as Phytophthora spp. and Plasmopara ssp. , in crops, especially potatoes, vines and tomatoes. The compound of Formula I and cymoxanil can be formulated in two ways: 1. Can the compound of Formula I and cymoxanil be formulated separately and applied separately, or applied simultaneously in an appropriate weight ratio? for example as a tank mix; or 2. the compound of Formula I and cymoxanil can be formulated together in the weight ratios defined herein. The fungicidal composition of the present invention comprises an effective amount of a mixture of the compound of Formula I and cymoxanil defined above as active ingredients, and at least one of a surfactant, a solid diluent or a liquid diluent. The composition of this invention is typically used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and / or a surfactant, wherein the formulation is consistent with the physical properties of the active ingredients., the mode of application and environmental factors such as the type of soil, humidity and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspoemulsions) and the like, which optionally can be thickened to gels. Useful formulations additionally include solids such as powders, fine powders, granules, pellets, tablets, films, and the like, which may be dispersible in water ("wettable") or water soluble. The active ingredients can be (micro) encapsulated and further formed in a suspension or solid formulation; alternatively the complete formulation of the active ingredients can be encapsulated (or "coated"). The encapsulation can control or retard the release of the active ingredients. The formulations that can be sprayed can be extended in suitable media and used as spray volumes from about one to several hundred liters per hectare. The high concentration compositions are used primarily as intermediates for their subsequent formulation. The formulations will typically contain effective amounts of active ingredients, diluent and surfactant within the following approximate ranges, amounting to 100 percent by weight.

Percent by weight Active Ingredients Diluent Surfactant Granules, Tablets and Powders 5-90 0-94 1-15 Water Dispersible and Water Soluble Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates) Powders 1 -25 0-99 0-5 Granules and Pellets 0.01-99 5-99. 99 0-15 Compositions of High Concentration 90-99 0-10 0-2 Typical solid diluents are described in Wat ins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd De., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd De., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, lists surfactants and recommended uses. All formulations may contain small amounts of additives to reduce foam, cake formation, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkylsulfo-succinates, alkyl sulfates, alkylbenzene sulphonates, organosilicon, N, N-dialkyltaurates, lignin sulphonates, condensed materials of naphthalenesulfonate-formaldehyde, polycarboxylates, and copolymers in polyoxyethylene / polyoxypropylene block. Solid diluents include, for example, clays such as bentonia, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N, N-dimethylformamide, dimethylsulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, olive oils, castor oil, linseed, tung (seeds of the Aleuritis cordata tree -Stend), sesame, corn, peanut, cottonseed, soybean, rapeseed and coconut, fatty acid esters, ketones • such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

The solutions, which include the emulsifiable concentrates, can be prepared simply by mixing the ingredients. The fine powders and the coarse powders can be prepared by mixing and, in general, ground such as in a hammer mill or a mill moved by energy of a fluid. The suspensions are usually prepared by wet milling; see, for example, U.S. 3, Q60,084. Granules and pellets can be prepared by spraying the active materials on preformed granular carriers, or by agglomeration techniques. See Browning, "Agglomeration," Chemical Enginerring, December 4, 1967, pages 147-48, Perry's Chemical Engineer's Handbook 4th, De., McGraw-Hill, New York, 1963, pages 8-57 et seq. And WO 91/13546. The pellets can be prepared as described in U.S. 4,172,714. The water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. The tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. The films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For additional information regarding the formulation technique, see U.S. 3,235,361, Col. 6, line 16 to Col. 1, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 to Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 to Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., IVeed Control Handbook, 8th De., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations were worked in the conventional manner.

Example A Wettable Powder 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone 27.9% cymoxani1 37.1% ether of dodecylphenolpolyethylene glycol 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0 %.

Example B Granules 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone 5.0% cymoxanil 5.0% granules of attapulgite (low content of volatile matter, 0.71 / 0.30 mm; USS No. 25-50 meshes) 90.0% EXAMPLE C Extruded pellets 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone 10.7% cymoxanil 14.3% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium bentonite / magnesium 59.0%.

Example D Emulsifiable concentrate 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinone 10.0% cymoxanil 10.0% mixture of oil-soluble sulfonates and polyoxyethylene esters 10.0% isophorone 70.0% The compositions of this invention are useful as control agents for plant diseases. The present invention further comprises a method for controlling plant diseases caused by fungal pathogens of plants, which comprises applying to the plant or portion thereof that is to be protected, or to the seed of the plant or seedling to be protected, an effective amount of a fungicidal composition of the compound of Formula I and cymoxanil. Alternatively, the fungicidal compositions containing only one of a compositions of the compound of Formula I and cymoxanil can be apj-followed followed by the application of the other composition. Additionally, separate compositions of the compound of Formula I and a cymoxanil composition can be combined as a physical mixture before their application, for example, a tank mix, and applied simultaneously. In any case, the compound of Formula I and cymoxanil are desirably applied in effective amounts to provide a control of a fungal disease that is greater than the additive control of that fungal disease provided by the compound of Formula I and cymoxanil individually. The compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the classes of Basidiomyete, Ascomycete, Deuteromycete and, in particular, the Oomycete class. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental crops, vegetables, field crops, cereals and fruits, particularly pathogens in potatoes, tomatoes and grapes. These pathogens include Plasmopara vi tícola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermantum, Al ternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recóndi ta, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxisporum, Verticillium dahliae, Pythium aphanidermatum, Phytophthora megasperma, Sclerotinia sclerotiorum, Scleroti um rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomyces graminis, Rynchosporium secalis, Fusarium , Bremia lactuacae and other genera and species closely related to these pathogens. Notable is its use to control Phytophthora infestans, which is a pathogenic agent involved in several fungal diseases (eg, late potato blight and late tomato wilt). Also notable is its use to control Plasmopara viticola, which is a pathogen involved in fungal diseases such as villous grape mold.

Laff compositions of this invention can also be mixed with one or more other insecticides, fungicides, nematoc * j.das, bactericides, acaricides, semiochemicals, repellents, attractants, pheromones, food stimulants or other biologically active compounds to form a multi-component pesticide, which gives an even broader spectrum of agricultural protection. Examples of such protectors agricultural substances with which the compositions of this invention can be formulated are: insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltamethrin, diafentiuron, diazino ?, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucitrinate, tau-fluvalide, fonofos, imidacolprid, isofenfos, malathion, metaldehyde, methamidophos, metidation, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, fosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinfos, thiodicarb, tralometrin, trichlorfon and triflumuron; fungicides such as azoxyestrobin (ICIA5504), benomyl, blasticidin-S, mixture. { Jordeaux (tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, ciproconazole, cyprodinil (CGA 219417), diclomezine, dichloran, difenoconazole, dimethomorph, diniconazole, diniconazole-M , dodine, ediphenphos, epoxiconazole (BAS 480F), fenarimol, fenbuconazole, fenpiclonil, fenpropidin, fenpropimorf, fluquinconazole, flusilazol, flutolanil, flutriafol, folpet, fosetil-aluminio, furalaxil, hexaconazol, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, cresoxim-methyl (BAS 490F), mancozeb, maneb, meprinil, metalaxyl, metconazole, myclobutanil, neo-asozin (ferric methanoarsonate), oxadixyl, penconazole, penicuron, probenazole, prochloraz, propiconazole, pirifenox, piroquij-on, sulfur, tebuconazole, tetraconazole, thiabendazole, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyclazole, triticonazole, uniconazole, validamycin and vinclozolin; nematocides such as aldoxicarb and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionate, chlorobenzilate, cyhexatin, dicofol, dienochlor, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexitiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis, delta endotoxin from Bacillus thuringiensis, baculovirus and bacteria, virus and entomopathogenic fungi. In certain cases, combinations with other fungicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Preferred for the best control of plant diseases caused by plant fungal pathogens (for example lower proportion of use or broader spectrum of controlled plant pathogens) or resistance management are mixtures of the compositions of this invention with a fungicide selected from the group of azoxystrobin (ICIA5504), copper salts (including the mixture of Bordeaux and copper oxychloride), fosetyl- aluminum, cresoxim-methyl (BAS 490F), metalaxyl, oxadiexil and mancozeb with fosetyl-aluminum and copper salts as the most useful. Specifically preferred mixtures of the two fungicides of this invention (compound refers to the compound of Formula I) with an additional fungicide are selected from the group: azoxystrobin (ICIA5504) and the mixture of cymoxanil and Compound I; copper salts and the mixture of cymoxanil and Compound I; fosetyl-aluminum and the mixture of cymoxanil and Compound I; cresoxim-methyl (BAS 490F) and the mixture of cymoxanil and Compound I; metalaxyl and the mixture of cymoxanil and Compound I; oxadixyl and the mixture of cymoxanil and Compound I; and mancozeb and the mixture of cymoxanil and Compound I. The control of plant diseases is usually achieved by applying an effective amount of a composition of this invention either pre- or post-infection, to the portion of the plant which is going to be protected such as roots, stems, foliage, fruit, seeds, tubers or bulbs, or the environment (soil or sand) in which they are growing the plants that are going to be protected. The composition can also be applied to the seeds, to protect the seeds and seedlings. The application rates for the compositions can be influenced by many environmental factors, and must be determined under the current conditions of use. The foliage can usually be protected when treated in a proportion from less than 1 g / 10, 000 m2 to 5,000 g / 10, 000 m2 (1 g / hectare to 5,000 g / hectare) of added active ingredient. The added active ingredient is defined as the total combined weight of active ingredients. Seeds and seedlings can usually be protected when the seeds are treated in a proportion from about 0.1 to 10 g of added active ingredient per kilogram of seed. The preferred foliar application of a composition of this invention are compositions containing from 1 to 400 g / 10, 000 m2 (1 to 400 g / hectare) of the compound of Formula I and from 4 to 240 g / 10, 000 m2 (4 at 240 g / ha) of cymoxanil as active ingredients. The following Examples demonstrate the compositions and methods of the present invention, and provide experimental evidence to determine the synergy between the compounds of Formula I and cymoxanil to control the late withered potato and tomato caused by Phytophthora infestans and villous grape mold caused by Plasmopara vi tícola. The control protection of the pathogen is provided by these compositions is not limited, however, to these species. However, the synergy demonstrated in the following Examples was not consistently observed under all conditions (for example heavy rain or washing) or for all plant diseases. EXAMPLE 1 Preparation of 5-Methyl-5- (4-phenoxyphenyl) -3-phenylamino-2, 4-oxazolidinedione (Compound I) A mixture of 14.3 grams of 2- (4-phenoxyphenyl) -ethyl ethyl ester (34 grams of a mixture containing 14.3 grams of ethyl 2- (4-phenoxyphenyl) lactate and 19.7 grams of diphenyl ether), 9.7 grams of 1,1-carbonyldiimidazole and 100 ml of methylene chloride was stirred at 25 ° C for 19 hours . Water (0.30 ml) was added and the mixture was stirred for 15 minutes. Then, 5 ml of acetic acid and 7.4 grams of phenylhydrazine were added. After stirring at 25 ° C for 24 hours, 100 ml of water are added. The pH was lowered to 2 with hydrochloric acid, and the aqueous layer was removed. After washing the methylene chloride layer with 50 ml of water, the solvent was evaporated under vacuum. The oily residue is mixed with 150 ml of hexane and 15 ml of ethyl acetate, warmed to 65 ° C, cooled to 20 ° C, and then filtered. The solids were washed with 100 ml of a mixture of 20 ml of ethyl acetate and 80 ml of hexane, and then dried. The title product (15.2 grams) was obtained with a melting point of 137-139 ° C. EXAMPLE 2 Synergistic Combination of 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil The test compositions were prepared as follows: A 182.5 mg of a 20% microemulsion containing Compound I (36.5 mg of active ingredient) 32 ml of distilled water was added to form a standard solution of Compound I. A 20% microemulsion of Compound I was prepared by mixing together 20% Compound I, 40% N - ethylpyrrolidinone and 40% Microstep H303 (all percentages by weight). Microstep H303 is an emulsifying mixture available from Stepan Co., Northfield, IL 60093. Cymoxanil is used as the commercially available 50% wettable powder (WP) formulation.

Curzate®. A standard solution was made by adding 32 ml of distilled water to 73 mg of the wettable powder formulation (36.5 mg of active ingredient). The standard solutions were then diluted with distilled water and applied by spray. The following dilutions were prepared to effect the application rates: Proportion (g / i Solution Distilled water a./10,000 m2) (1) Standard (ml) (ml) 8 0.5 59.5 35 2 58 70 4 56 140 8 52 280 16 44 (1) grams of active ingredient per hectare. For applications of a single active ingredient, the total spray volume is equal to the volume of standard pattern plus the volume of distilled water added to achieve the desired ratio. For the simultaneous application of Compound I and cymoxanil, the appropriately diluted standard solutions containing Compound I or cymoxanil were combined and then applied by spraying.

Potatoes (Solanum tuberosum "Superior"), grown from tissue cultures were transplanted into pots of 10.16 cm (4 inches) in diameter and kept in the greenhouse. Five to six weeks after the transplant, uniform plants of 15.24-20.32 cm (6-8 inches) high were selected. The plants were sprayed with cymoxanil only in proportions of 8, 35 and 140 grams of ia / 10,000 m2 (8, 35 and 140 grams of ai / hectare) or with Compound I only in proportions of 8, 35 and 140 g of ia / 10,000 m2 ( 8, 35 and 140 g ai / hectare) or with combinations of cymoxanil and Compound I in all combination proportions. After spraying the plants were kept in a greenhouse for 6 days. The plants were then inoculated with the aerosol suspension of zoospores of P. infestans (2 x 104 zoospores / ml) in deionized water. The plants were immediately placed in a humidification chamber (> 98% relative humidity) for 24 hours, to provide the environmental conditions necessary for infection after this and, following a transition period of 24 hours in a growth chamber illuminated, the plants were returned to the greenhouse. The disease was evaluated 6 days after the inoculation, recording the percentage of surface of the leaf with typical lesions of P. infestans on the four fully expanded basal leaves. Each treatment was performed in duplicate 3 times for each test. The average percentage of control of the disease is summarized in Table 1. Tests where the level of control is greater than simply additive are indicated by an asterisk.

TABLE 1 Synergistic Effect of Compounds of Compound I / Cymoxanil on Late Withered Potato Percentage of Disease Control Compound Proportion "• 9. ia / Experimental (2> Expected131 10,000 m2 Test 1 Test 2 Average Test 1 Test 2 Mean cymoxanil 8 0 20 10 - - -cymoxanil 35 0 25 12.5 - - -cymoxanil 140 41 51 46 - - - Compound I 8 69 77 73 - - - Compound I 35 87 98 92.5 - - - Compound I 140 90 98 94 - - - Cymoxanil +1 8 + 8 * 77 * 95 * 86 69 82 76 Cymoxanil +1 8 + 35 * 98 98 * 98 87 98 93 Cymoxanil +1 8 + 140 * 95 * 99 * 97 90 98 95 Cymoxanil +1 35 + 8 * 75 74 74.5 69 83 76 Cymoxanil +1 35 + 35 * 91 98 * 94.5 87 99 93 Cymoxanil +1 35 + 140 * 98 * 100 * 99 90 99 95 Cymoxanil +1 140 + 8 * 95 86 * 90.5 82 89 85 Cymoxanil +1 140 + 35 * 98 * 100 * 99 92 99 96 Cymoxanil +1 140 + 140 * 98 98 * 98 94 99 97 (i) grams of active ingredient per hectare. . { 2) current control observed. (3) calculated expected control of the Colby equation.

EXAMPLE 3 Synergistic combination of 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil The test compositions were prepared as follows: A standard solution of Compound I was prepared from 1825 mg of a 2% emulsifiable concentrate (EC) containing Compound I (36.5 mg of active ingredient) as described in Example 2. A 2% EC of Compound I was prepared by dissolving 25.51 g of Compound 1 in a mixture of solvent consisting of 37.5 g of Atlox® 3453, 37.5 g of Atlox® 3404, 62.5 g of n-butanol, and 1112.5 g of acetophenone. Atlox® 3453 and Atlox® 3494 are available from ICI Americas, Inc., New Murphy Road and Concord Pike, Wilmington, Delaware 19807. A standard solution of cymoxanil was prepared from a 50% WP formulation of Curzate® in a manner similar to that described in Example 2. The standard solutions were then diluted with distilled water as described in Example 2, to effect application rates of 70 g ai / 10,000 m2 (70 g ai / hectare), 140 g of ia / 10,000 m2 (140 g of ai / hectare), and 280 g of ia / 10,000 m2 (280 g of ai / hectare). These dilutions were then applied to the Spray test plants, following the procedures described in Example 2. The composition prepared above was tested as follows. The test conditions are identical to those described for Example 2, except that (i) the test rates for cymoxanil were 70 and 140 g ai / 10,000 m2 (70 and 140 g ai / hectare), ( ii) the test proportions of Compound I were 140 and 280 g ai / 10,000 m2 (140 and 280 g a? a / hectare) and (iii) the plants were kept in a greenhouse for 2 days after spraying, and then they were inoculated. The average percentage of control of the disease is summarized in Table 2. Tests where the level of control is greater than simply additive are indicated by an asterisk.

TABLE 2 Synergistic Effect of Compounds of Compound I / Cymoxanil on Late Withered Potato Percentage of Disease Control Compound Proportion q ia / h'11 Experimental (21 Espeí: ado13 'cymoxanil 70 14 -cymoxanil 140 56 - Compound I 140 62 - Compound I 280 71 - CCyymmooxxaanniill ++ 11 7700 ++ 114400 * 81 67 Cymoxanil +1 70 + 280 * 89 83 Cymoxanil +1 140 + 140 * 77 75 Cymoxanil +1 140 + 280 * 91 87 (i) grams of active ingredient per hectare. (2) observed current control. (3) calculated expected control of the Colby equation.

JEMPLO 4 Synergistic combination of 5-methyl-5- (4-phenoxyphenyl) -3- phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil A 2% CE of Compound I was prepared by the procedure described in Example 3 Standard solutions and dilutions of Compound I and Cymoxanil were prepared by the procedures described in Example 3. Those dilutions were then applied to the spray test plants, following the procedures described in Example 2.

Potatoes (Solanum tuberosum "Superior") grown from tissue culture were transplanted into 10.16 cm (4 inch) pots and kept in a greenhouse. Five to six weeks after the transplant, uniform plants of 15.24-20.32 cm (6-8 inches) high were selected. The plants were sprayed with cymoxanil only in proportions of 70 and 140 g ai / 10,000 m2 (70 and 140 g ai / hectare), or with Compound I only in proportions of 140 and 280 g ai / 10,000 m2 (140 and 280 g of ai / hectare) or with combinations of cymoxanil and Compound I in all proportion combinations. After spraying, the plants were kept in a greenhouse for 6 days. The plants were then inoculated with an aerosol suspension of P. ínfestans zoospores (2 x 104 zoospores / ml) in deionized water. The plants were immediately placed in a humidification chamber (> 98% relative humidity) for 24 hours, to provide the environmental conditions necessary for infection after this. After the humidification period, the plants were sprayed a second time with the same treatments applied previously. After drying, the plants were given a 24 hour transition period in an illuminated growth chamber, and returned to the greenhouse. The disease was evaluated 6 days after inoculation, recording the percentage of the surface of the leaf with typical lesions of P. infestans on the four true basal leaves fully extended. Each treatment was done by replicating 3 times. The average percentage of control of the disease is submerged in Table 3. Tests where the level of control is greater than simply additive are indicated by an asterisk.

TABLE 3 Synergistic Effect of Combinations of Compound I, / Cy? moxanil on Late Withered > of the Potato Porcent aj e of • control of the disease Compound Proportion q ia / h Experimental 12 'Is it preferable' 3 'cymoxanil 70 65 -cymoxanil 140 91 - Compound I 140 62 - Compound I 280 80 - Cymoxanil + 1 70 + 140 * 92 86 Cymoxanil +? 70 + 280 * 99 93 Cymoxanil + 1 140 + 140 * 99 96 Cyoxoxanil + 1 140 + 280 * 100 98 (i) grams of active ingredient per hectare. (2) observed current control. (3) calculated expected control of the Colby equation.

? JEMPLO 5 Synergistic combination of 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil This test was performed using compositions of Compound I and cymoxanil which were prepared by dissolving each compound in acetone and then diluting each solution with water containing a nonionic surfactant to give a final standard solution consisting of the active ingredient in acetone: water containing 1: 1 0.02% by volume of a non-ionic surfactant. The dilutions were prepared from a similarly to those described in Example 2. These dilutions were then applied to the spray test plants, following the procedures described in Example 2. After spraying, the plants were returned to the greenhouse. On day 1 after the spray, the plants were moved to a humidification chamber (> 98% relative humidity) for 8 hours and in that time they were placed in an illuminated growth chamber (20 ° C) for 16 hours . This cycle was repeated on day 2 after the spraying. On day 3 after the spraying, the plants were returned to the greenhouse and maintained for 3 days until inoculation. The plants were then inoculated with an aerosol suspension of P. ínfestans zoospores (2 x 104 zoospores / ml) of deionized water. The plants were immediately placed in a humidification chamber (> 98% relative humidity) for 24 hours, to provide the environmental conditions necessary for infection after this and, following a transition period of 24 hours in a chamber of illuminated growth, the plants were returned to the greenhouse. The disease was evaluated 6 days after the inoculation recording the percentage of surface of leaves with typical lesions of P. infestans on the four true basal leaves fully extended. Each treatment was done by replicating 5 times for each test. The test was repeated twice, and the average percentage of control of the disease is submerged in Table 4 is the average of both tests. Locks where the level of control is greater than simply additive are indicated by an asterisk. TABLE 4 Synergistic Effect of Compounds of Compound I / Cymoxanil on Wilted Tardic > of the Porcent Potato: control of the disease Compound Proportion g ia / h (1) Experimental t21 Expected131 cymoxanil 100 38 -cymoxanil 250 47 -cymoxanil 625 41 - Compound I 15 59 - Compound I 30 66 - Compound I 60 91 - Compound I 120 94 - Cymoxanil +1 100 + 15 48 75 Cymoxanil +1 100 + 30 * 80 79 Cymoxanil +1 100 + 60 * 98 94 Cymoxanil +1 100 + 120 96 96 Cymoxanil +1 250 + 15 45 78 Cymoxanil +1 250 + 30 * 84 82 Cymoxanil + 250+ 60 * 97 95 Cymoxanil +1 250 + 120 95 97 Cymoxanil + f 625 + 15 68 76 Cymoxanil +1 625 + 30 * 96 80 Cyrioxanil +1 625 + 60 * 100 95 Cymoxanil +1 625 + 120 * 99 96 (i) grams of active ingredient per hectare. (2) observed current control, average of two separate tests. (3) calculated expected control of the Colby equation.

EXAMPLE 6 Synergistic combination of 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil This test was performed using the compositions of Compound I and cymoxanil which were prepared by dissolving each compound in acetone and then diluting each solution with water containing a non-ionic surfactant, to give a final standard solution consisting of the active ingredient in acetone: water 1: 1 containing 0.02% by volume of a non-ionic surfactant. Dilutions were prepared in a manner similar to that described in Example 2. These dilutions were then applied to the spray test plants, following the procedures described in Example 2. Vine plantlets (Vi tis vinifera) were grown. Chardonnay ") in square plastic pots of 5 cm (2 inches), and were kept in a growth chamber at 27 ° C and a photoperiod of 16 hours. When the plants were approximately 5-10 cm high (2-4 cm) inches high), uniform plants were selected for the test. The plants were sprayed with cymoxanil only at 7.8, 31.3, 125 and.50.0 g ai / 10, 0.00 m2 (.7.8, .31.3, .125 and 500 g ai / hectare), or with Compound I only , provides.de 0.31, 1.25, .5 and .20 g of. ia / 1.0, 0.0.0 m2 (0.3.1, 1.25, 5 and 20 g ai / hectare), or with combinations of cymoxan ^ l and Compound I in all proportion combinations. After spraying, the plants were returned to the growth chamber. On day 1 after the spray, the plants were moved to a humidification chamber (> 98% relative humidity) for 16 hours, and in that time they were returned to the growth chamber for 8 hours. This cycle was repeated on days 2, 4 and 5 after the spray. On day 6 after the spraying, the plants were regressed to the growth chamber, and were maintained for one day until inoculation. The plants were then inoculated with an aerosol suspension of zoospores of Plasmopara tícola (2.5 x 104 zo.asparas / ml) in deionized water ^ The inoculated plants were immediately placed in a humidification chamber for 24 hours, to provide the environmental conditions necessary for the infection. The plants were then returned to the growth chamber for 6 days, and in that time they were returned to the chamber of Humidification for 24 hours to induce sporulation. The severity of the disease was evaluated by recording the percentage of leaf surface with typical lesions of P. vi ticola and sporulation on the three true, fully expanded basal leaves of each plant. Each treatment was done by replicating 5 times for each test. The average percentage of control of the disease [((% of disease in reviewed) - (% of treated diseases)) / (% of disease in reviewed) X 100] is summarized in Table 5. The tests where the level of Control is greater than simply additive are indicated by an asterisk.

TABLE 5 Synergistic Effect of Combinations of Compound I / Cymoxanil on Grape Vellum Percentage and control of the disease Compound Proportion g ia / h Expected Experimental 'cymoxanil 7.8 2 cymoxanil 31.3 3 symoxanil 125 28 cymo-xanil 500 99 Compound I 0.31 20 Compound I 1.25 18 Compound I 5 71 Compound I 20 99 Cymoxanil +1 7.8 + 0.31 4 22 Cymoxanil +1 7.8 + 1.25 15 20 Cymoxanil +1 7.8 + 5 * 77 72 Cymoxanil +1 7.8 + 20 99 99 Cymoxanil +1 31.3 + 0.31 2 22 Cymoxanil +1 31.3 + 1.25 16 20 Cymoxanil +1 31.3 + 5 64 72 Cymoxanil +1 31.3 +20 98 99 Cymoxanil +1 125 + 0.31 34 47 Cymoxanil +1 125 + 1.25 * 87 41 Cymoxanil +1 125 + 5 * 96 79 Cyanoxanil +1 125 + 20 99 99 Cymoxanil +1 500 + 0.31 * 100 99 Cymoxanil +1 500 + 1.25 100 100 Cymoxanil +1 50T + 5 100 100 Cymoxanil +1 500 + 20 99 100 (i) grams of active ingredient per hectare. (2) observed current control, average of two separate tests. (3) calculated expected control of the Colby equation.

EXAMPLE 7 Synergistic combination of -5-methyl-5- (4-phenaxy-phenyl) -3-phenylamino-2,4-oxazolidinedione (Compound 1) and Cymoxanil The test compositions were prepared as follows: A portion of a suspension concentrate of 200 g / 1 (20% SC) containing Compound I was diluted with 2000 parts of distilled water to form a test solution of 100 ppm (parts per million) of Compound I. A suspension concentrate of 200 g / 1 of Compound I was prepared from Compound I (204.08 g, 98%), Supermontaline SLT 70 (4.0 g), monopropylene glycol (50.0 g), Rhodorsil 454 (2.0 g), acetic acid (33.67 g, 80%), sodium acetate tifihydrate (62.0 g), Bronopol (1.0 g), Attagel 50 (10.0 g), -water. { 509.25 g), Emcol® -4100 (50.0 g), Culminal MHPC50 (1.0 g) and Atplus 469 (200.0 g) for the preparation of a slurry combining Compound I, Supermontaline SLT 70, monopropylene glycol, half d ^ l Rhodorsil 454, acetic acid, sodium acetate trihydrate, Bronopol, Attagel 50, most of water, Emcol® 4100-, Culminal MHPC5Q and Atplus 469 (as a 5% aqueous solution prepared with part of the water) under mixed; the watery paste was stirred then for an hour before being wet milled with a Dynomill; the mixing chamber is 85-87% (by volume) filled with glass beads having a diameter range of 0.5-0.75 mm, the peripheral speed of the mill discs was adjusted to 14 m / s, the paste was watered the mill was fed at a speed of 40 ml / minute, and two passes were necessary to achieve the desired particle size (average particle size below 1 μm); the remaining half of Rhodorsil 454, Atplus 469 and the remaining part of the water were added successively under stirring, and the suspension was stirred for half an hour. Cymoxan ™ was used as the wettable powder formulation when 50% commercially available from Curzate®. A portion of the WP of 50% cymoxanil was diluted with 5000 parts of distilled water to form a test solution of 100 ppm cymoxanil. A portion of the suspension concentrate of 100 g / 1 + 100 g / 1 (CS 10% + 10%) containing Compound I and cymoxanil was diluted with 1000 parts and 2000 parts of distilled water, to form 100 + test solutions 100 ppm and 50 + 50 ppm of Compound I and cymoxanil, respectively. A suspension concentrate of 100 g / 1 + 100 g / 1 (CS 10% + 10%) of Compound I and cymoxanil was prepared from Compound I (102.04 g, 98%), cymoxanil (104.17 g, 96%), Supermontaline SLT 70 (2.0 g), monoprouilenglicol (50.0 g), Rhodorsil 454 (2.0 g), acetic acid (26.73 g, 80%), sodium acetate trihydrate (16.37 g), Bronopol (1.0 g), Attagel 50 (2.50 g), Reax 85 (25.0) g), Morwet D425 (12.5 g), Aerosil 200 (2.50 g), Kelzan® S (0.10 g), Brij 78 (200.0 g) and water (552.66 g) for the preparation of a watery paste, adding the main part of Compound 1 and heating to 60 ° C; adding Brij 78, acetic acid and sodium acetate trihydrate under mixed, and waiting until Brij 78 was completely dissolved; Supermontaline SLT 70, monopropylene glycol, half of Rhodorsil 454, Bronopol, Attagel 50, Reax 85, Morwet D425, Aerosil 200, the remaining part of Compound 1 and cymoxanil were added under mixed while the paste was cooled at room temperature; the gummy paste was then stirred for one hour before being wet-milled with a Dynomill; the milling chamber is 85-87% full (by volume) with glass beads having a diameter in the range of 0.5-0.75 mm, the peripheral speed of the mill discs was adjusted to 14 m / s, the paste gaseous was fed to the mill at a rate of 40 ml / minute and two bases were necessary to achieve the desired particle size (average particle size below 1 μm); the remaining half of the Rhodorsil 454 and the Kelzan® S (as a 2% aqueous solution prepared with the remaining part of the water) was added to the ground slurry with stirring, and the suspension was stirred for half an hour. Tomatoes (Houryu variety) were grown in a greenhouse. The test has five duplicates (each duplicate of a plant per pot). The test solutions were applied in 100 ml per pot (equivalent to 3000 1 / 10,000 m2 (3000 1 / hectare), the test solutions of 100 parts per million and 50 parts per million provide application ratios equivalent to 300 g / cm2 (3-00 g / hectare) and 150 g / 10, 000 m2 (150 g / hectare), respectively). The plants were sprayed the next day with a suspension of zoospores of Phytphthora infestans, the cause of the late tomato wilt. This inoculation was done using a small sprinkler to deposit the inoculum on eight leaves of each plant. After inoculation, the pots were kept in an incubator illuminated at 23 ° C and 100% relative humidity for two days. All eight leaves inoculated per plant were evaluated the next day by recording the percentage of leaf surface with P. inestans lesions. The average percentage of control of the disease is submerged in Table 6.

Treatments where the level of control is greater than simply additive are indicated by asterisks.

TABLE 6 Synergistic Effect of Combinations of Compound I / Cymoxanil on Late Withered Tomato Percentage of Disease Control Compound Proportion g ia / h1 Experimental Expected cymoxanil (50% WP) 300 93 Compound I (20% CS) 300 74 Cymoxanil + T (10% + 10% CS) 300 + 300"100 98 Cymoxanil +1 (10% + 10% CS) 150 + 150 * 100l (1) grams of active ingredient per hectare. (2) observed current control, average of two separate tests. (3) expected control calculated from the Colby equation. (4) 300 g total of ai / 10, Q00 m2 (300 g total ai / hectare) of composition 1: 1 provides a control greater than 300 g ai / 10, 000 m2 (300.g ai / hectare ) of any of the compounds alone.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Having described the invention as above, property is claimed as contained in the following:

Claims (10)

1. REV IVICINICATIONS 1. A fungicidal composition characterized in that it comprises: a fungicidally effective amount of a mixture of (a) at least one compound selected from 5-methyl-5- (4-phenoxyphenyl) -3-phenylamino- 2,4-oxazolidinone and agriculturally suitable salts thereof, and (b) at least one compound selected from cymoxanil and the suitable salts from the agricultural point of view thereof, wherein the weight ratio of the component ( a) component (b) is from 17: 1 to 1: 100.
2. 2. A fungicidal composition according to claim 1, characterized in that it additionally comprises at least one of a surfactant, a liquid diluent or a liquid diluent.
3. 3. A fungicidal composition according to claim 2, characterized in that the weight ratio of component (a) to component (b) is from 8: 1 to 1:25.
4. 4. A fungicidal composition according to claim 3 ', characterized in that the weight ratio of component (a) to component (b) is from 4: 1 to 1:10.
5. 5. A fungicidal composition according to claim 4, characterized in that the weight ratio of component (a) to component (b) is from 3: 2 to 1: 3.
6. 6. A method for controlling plant diseases caused by plant fungal pathogens, characterized in that it comprises: applying to the plant or portion thereof that is to be protected, or to the seed of the plant or seedlings to be protected , an effective amount of a fungicidal composition comprising (a) the compound of Formula I or a suitable salt from the agricultural point of view, (b) cymoxanil, or a suitable salt from the agricultural point of view thereof, and (c) at least one of a surfactant, a solid diluent or a diluent liquid; the weight ratio of the compound of (a) to the compound of (b) applied is from about 17: 1 to 1: 100, and the compound of (a) and the compound of (b) are applied in effective amounts to provide the control of the fungal disease which is greater than the additive control of that fungal disease provided by the compound of (a) and the compound of (b) individually.
7. 7. The method according to claim 6, characterized in that the fungal pathogen of the plant is Phytophthora infestans.
8. 8. The method according to claim 6, characterized in that the plant fungal pathogen is Palsmopara vi tícola.
9. 9. A method for controlling plant diseases caused by plant fungal pathogens, characterized in that it comprises: applying sequentially in any order to the plant or portion thereof to be protected, or to the seeds of the plant or seedlings that are going to be protected. to be protected, (i) an effective amount of a first composition comprising (a) the compound of Formula I or an agriculturally suitable salt thereof, and (cl) at least one of a surfactant, a solid diluent or a liquid diluent; and (ii) an effective amount of a second composition comprising (b) cymoxanil, or a suitable salt from the agricultural point of view thereof, and (c) at least one of a surfactant, a solid diluent or a liquid diluent; the weight ratio of the compound of (a) to the compound of (b) applied is from about d 17: 1 to 1: 100, and the compound of (a) and the compound of (b) are applied in effective amounts to provide the control of the fungal disease which is greater than the additive control of that fungal disease provided by the compound of (a) and the compound of (b) individually.
10. 10. A method for controlling plant diseases caused by plant fungal pathogens, characterized in that it comprises: applying to the plant or portion thereof that is to be protected, or to the seeds of the plant or seedlings to be protected, a effective amount of a physical mixture of (i) a first composition comprising (a) the compound of Formula I or an agriculturally suitable salt thereof, and (cl) at least one of a surfactant, a solid diluent or a liquid diluent; and (ii) a second composition comprising (b) cymoxanil, or an agriculturally suitable salt thereof, and (c2) at least one of a surfactant, a solid diluent or a liquid diluent; the weight ratio of the compound of (a) to the compound of (b) applied is from about 17: 1 to 1: 100, and the compound of (a) and the compound of (b) are applied in effective amounts to provide the control of fungal disease that is greater than the additive control of that fungal disease provided by the compound of (a) and the compound of (b) individually.