JP2001510454A - Fungicidal composition containing acylaminobenzamide (compound A) and method for producing compound A - Google Patents

Abstract

(57) Abstract: A fungicidal composition comprising the compound (A) as a first component and the use of the compound for combating fungal infection of plants. Further claimed is a process for preparing compounds of formula (I) wherein R is halogen or C _1-4 alkyl.

Description

The present invention relates to a method for producing an acylaminobenzamide, a composition containing an acylaminobenzamide, and a fungal infection of a plant. And a method of using the composition for eradication. Fungicidal acylaminobenzamides are disclosed in EP-A1-0381330, EP-A1-0470711, EP-A1-0468683, EP-A1-0468682, WO93 / 14063 and WO94 / 00422. Compound No. 38 listed in Table 1 of EP-A1- 0381330 has the following structure: Which is hereinafter referred to as Compound A. The present invention provides compounds of formula (I): Wherein R is halogen or C _1-4 alkyl; a compound of formula (II): Is a compound of formula (III): Provided above. Alkyl is straight or branched, for example methyl. Halogen is preferably fluorine or chlorine. Preferably, R is chlorine. Preferably, the method of the present invention is performed in a solvent. Preferred solvents include alcohols (especially methanol), polar solvents (such as acetonitrile, N, N-dimethylformamide or N-methylpyrrolidone), hydrocarbons (such as toluene or xylene) or ethers (tetrahydrofuran or 1,2-dimethoxyethane) )including. This method is preferably carried out in a temperature range of 20 to 120 ° C (20 to 100 ° C, particularly 20 to 80 ° C). The process of the present invention is carried out in the presence of a suitable base such as a methoxide, carbonate, hydride, hydroxide or the like of an alkaline earth metal (such as calcium or magnesium) or preferably an alkali metal (such as sodium or potassium). Is preferred. Examples of suitable bases include sodium methoxide, potassium carbonate, sodium hydride and sodium hydroxide. In one aspect, the present invention provides a method of making a compound of formula (I), wherein the method is in the presence of a surfactant (alkoxylate [eg SYPERONIC NP13]) or polyethylene glycol [eg REG300]. carry out. Typically, the process of the present invention is performed by adding a compound of formula (II) to a stirred slurry of a suitable base in a suitable solvent, optionally in the presence of a surfactant. Next, the compound of the formula (III) is added and the mixture is stirred in a temperature range of 20-120 ° C (particularly 20-80 ° C) for an appropriate time (for example, 1-5 hours). Compounds of formula (I) can be purified using standard literature procedures. The present invention further provides Compound A as the first active ingredient; kresoxim-methyl (also known as BAS490F), azoxystrobin (ICIA5504) as the second active ingredient. ), SSF126, N-methyl 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamide, famoxadone, fluazinam, fluazinam, 5- (4-fluorophenyl)- 2-methoxy-5-methyl-3-phenylamino-1,3-imidazolin-4-one, 5-methyl-5- [4- (2-methyl-4-thiazolylmethoxy) phenyl] -3-phenyl Amino-1,3-oxazolidine-2,4-dione, 5 (4-fluorophenyl) -5-methyl-2-methylthio-3-phenylamino-1,3-imidazolin-4-one, 2-ethyl-5 -(4-fluorophenyl) -5-methyl-3-phenylamino-1,3-imidazolin-4-one or (5S) -5-methyl-2-methyl Thio-5-phenyl-3-phenylamino-1, 3-imidazoline-4-one; provide and suitable carrier or fungicidal compositions comprising a diluent. In one particular aspect, the present invention provides a fungicidal composition comprising Compound A as a first active ingredient; kresoxime-methyl, azoxystrobin or fluazinam as a second active ingredient; and a suitable carrier or diluent. In another aspect, the present invention provides a fungicidal composition comprising Compound A as a first active ingredient; kresoxime-methyl or azoxystrobin as a second active ingredient; and a suitable carrier or diluent. In another aspect, the invention relates to a composition comprising a weight ratio of the first active ingredient to the second active ingredient in the range of 1:10 to 10: 1 (particularly in the range of 1: 7 to 2: 1, for example 1: 4 to 2: (1 range). The compositions of the present invention are fungicidal and can be used to control one or more of the following pathogens: Erysiph e graminis (barley fungus) and hops on barley, wheat, rye and lawn. Uncerul a neator such as Sphaerotheca macularis, Sphaerotheca fuliginea on Cucurbitaceae (eg, cucumber), Podosphaera leucotricha on apples, and Uncinul a neator on grape. Other powdery mildew fungi on various hosts; Botrytis cinerea (grey mold) on tomatoes, strawberries, vegetables, grapes and other hosts; and other botulinum species on other hosts; Plasmopara on grape Viticola (plasmopara viticola); lettuce Peronospora species on soybean, tobacco, onion and other hosts, Pseudoperonospora humuli on hops, and Pseudoperonospora cubensis on cucurbitaceae, Bremia lactucae, soybean, tobacco, onion and other hosts (Pseudoperonospora cu bensis) and other Phytophthora infestans on potatoes and tomatoes and other phytoftra on vegetables, strawberries, avocados, peppers, houseplants, tobacco, cocoa and other hosts seed. In another aspect, the present invention provides a method for combating fungi comprising applying a fungicidally effective amount of a composition as described above to a plant, plant seed or plant or seed locus. The type of composition used in any case depends on the particular purpose envisioned. All compositions, whether solid or liquid, preferably contain 0.0001-95%, more preferably 1-85%, for example 1-25% or 25-60%, of the active ingredient mixture described above. When applied to the leaves of a plant, the total weight of active ingredient is 0.1 per hectare. The composition is applied at a rate of 1 g-10 kg, preferably 1 g-8 kg, more preferably 10 g-4 kg. When used as a seed dressing, the total weight of the active ingredient per kg of seed is 0.0001 g (eg, 0.001 g or 0.05 g) -10 g, preferably 0.005 g-8 g, more preferably 0.005 g. The composition is used in a proportion of -4 g. The composition of the present invention can be applied in many ways. For example, it may be applied directly to the leaves, seeds or the medium in which the plants are grown, or may be sprayed, sprayed, applied in a cream or paste formulation, or applied as steam or sustained release granules. You may. Can be applied to any part of the plant, including leaves, stems, branches or roots, or to the soil around the roots, or to seeds before planting, or to soil in general, or to paddy water, or to a hydroponic system It is possible. The composition may be infused into plants or sprayed onto vegetation using electrodynamic spraying or other minor methods, or applied to land or aerial irrigation systems. The term "plant" as used herein includes seedlings, shrubs, trees. In addition, the fungicidal methods of the present invention include protection, protection, prevention systems and eradication measures. The composition comprises a solid diluent or carrier, such as kaolin, bentonite, diatomite, dolomite, calcium carbonate, talc, powdered magnesium, fuller, gypsum, diatomaceous earth, dustable powders or granules containing fillers such as china clay. It may be in the form of Such granules are preformed into granules suitable for application to soil without further treatment. These granules can be prepared by impregnating the filler pellets with the active ingredient or by pelletizing a mixture of the active ingredient and a powder filler. Compositions for dressing seeds can include agents (eg, mineral oil) that help the composition adhere to the seeds; or organic solvents (eg, N-methylpyrrolidone, propylene glycol, or N, N-dimethylformamide). ) Can be used to formulate the active ingredients for seed dressing applications. The composition can also be in the form of water-dispersible powders or granules, which include a wetting or dispersing agent that allows for dispersion in the liquid. Powders and granules may also contain fillers and suspending agents. The composition may be in the form of a soluble powder or granules, or a solution in a polar solvent. Soluble powders are prepared by mixing the active ingredient with a water-soluble salt (eg, sodium bicarbonate, sodium carbonate, magnesium sulfate or polysaccharide), and a wetting or dispersing agent to improve water dispersibility / solubility. Is also good. The mixture is then ground into a fine powder. Similar compositions can be granulated to form water-soluble granules. The active ingredient can be dissolved in polar solvents, for example, ketones, alcohols and glycol ethers to produce a solution. These solutions may contain a surfactant to improve water dilutability and prevent crystallization in the spray tank. An emulsifiable concentrate or emulsion is obtained by dissolving the active ingredient in an organic solvent which may also contain a wetting or emulsifying agent, and then adding this mixture to water which may also contain a wetting or emulsifying agent. Can be manufactured by Suitable organic solvents are aromatic solvents such as alkylbenzenes and alkylnaphthalenes, ketones such as cyclohexanone and methylcyclohexanone, chlorinated hydrocarbons such as chlorobenzene and trichloroethane, and alcohols such as benzyl alcohol, furfuryl alcohol, butanol and glycol ether. . Aqueous suspension concentrates of almost insoluble solids can be prepared by ball or bead milling together with a dispersing agent together with a suspending agent to stop solidification. The composition used as a spray may be in the form of an aerosol that holds the formulation in a container under the pressure of a suitable propellant. The active ingredient can be mixed dry with the pyrotechnic mixture into a composition suitable for producing smoke containing the active ingredient in an enclosed space. Alternatively, the compositions can be used in microencapsulated form. The active ingredient can also be formulated for sustained release by formulation in a biodegradable polymer formulation. By including suitable additives, such as additives to improve uptake, distribution, adhesion and the resistance of the treated surface to rain, the compositions of the present invention can be further applied to a variety of uses. Other additives may be included to improve the biological effectiveness of the various compositions. Such additives can be surfactants to improve wetting and retention on the formulation-treated surface and uptake and mobility of the active ingredient, or oil-based spray additives, such as Additives of certain mineral and natural vegetable oils (such as soybean and rapeseed oil) or blends of these with another adjuvant may be included. The composition can be used as a mixture with a fertilizer (eg, a nitrogen-, potassium- or phosphate-containing fertilizer). Preference is given to compositions which contain only the active ingredient, for example granules or fertilizers, coated with the active ingredient. Suitably, such granules will contain up to 25% by weight of the active ingredient. Water-dispersible powders, emulsifiable concentrates and suspension concentrates usually contain a surfactant such as a wetting agent, dispersing agent, emulsifying agent or suspending agent. These surfactants are cationic, anionic or nonionic. A suitable cationic surfactant is a quaternary ammonium compound, such as cetyltrimethylammonium bromide. Suitable anionic surfactants are soaps, salts of aliphatic monoesters of sulfuric acid (eg, sodium lauryl sulfate), and salts of sulfonated aromatic compounds (eg, sodium dodecylbenzenesulfonate, sodium lignosulfonate, calcium or ammonium, Butylnaphthalenesulfonate, and mixtures of diisopropyl- and sodium triisopropylnaphthalenesulfonate). Suitable nonionic surfactants are the condensation products of ethylene oxide with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or alkylphenols (such as octylphenol or nonylphenol and octylcresol). Other nonionic surfactants are partial esters derived from long-chain fatty acids and hexitol anhydrides, alkyl glucosides, polysaccharides and lecithin and the condensation products of said partial esters with ethylene oxide. Suitable suspending agents are hydrophilic colloids (eg, polyvinylpyrrolidone and sodium carboxymethylcellulose), and swellable clays such as bentonite or attapulgite. Compositions for use as aqueous dispersants or emulsions are generally provided in the form of a concentrate containing a high proportion of the active ingredient, which is diluted with water before use. These concentrates are preferably capable of withstanding long-term storage and capable of being diluted with water to form an aqueous preparation that retains sufficient uniformity over time to be applicable with conventional spray equipment. . Concentrates conveniently contain up to 95%, suitably 1-85%, for example 1-25% or 25-60% by weight of active ingredient. After dilution to form an aqueous preparation, such preparations contain various amounts of the active ingredient, depending on the intended use, but are preferably 0.0001-10% by weight, for example 0.005-10% by weight, of the active ingredient. Aqueous preparations containing The compositions of the present invention can include other compounds having biological activity, such as compounds having similar or complementary fungicidal activity, or compounds having plant growth control, herbicidal, or insecticidal activity. By including other fungicides, the resulting composition can have a broader spectrum of activity and a greater level of intrinsic activity than a composition comprising only the first and second active ingredients. In addition, other fungicides can have a synergistic effect on the fungicidal activity of the first or second active ingredient. Examples of fungicidal compounds that can be included in the composition include (RS) -1-aminopropylphosphonic acid, (RS) -4- (4-chlorophenyl) -2-phenyl-2- (1H-1,2 , 4-Triazol-1-ylmethyl) butyronitrile, (Z) -N-but-2-enyloxymethyl-2-chloro-2 ', 6'-diethylacetanilide, 1- (2-cyano-2-methoxyiminoacetyl ) -3-Ethylurea, 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile, 4-bromo-2-cyano-N, N-dimethyl- 6-trifluoromethylbenzimidazole-1-sulfonamide, 5-ethyl-5,8-dihydro-8-oxo (1,3) -dioxole- (4,5-g) quinoline-7-carboxylic acid, α- [N- (3-chloro-2,6-xylyl) -2-methoxyacetamido] -γ-butyrolactone, N- (2-methoxy-5-pyridyl) -cyclopropanecarboxamide, alanicarb (alanyca rb), aldimorph ), Ampropi Rufos (ampropylfos), anilazine (anilazine), azaconazole (azaconazole), benalaxyl (benalaxyl), benomyl (benomyl), viloxazole (biloxazol), binapacryl (binapacryl), bitertanol (bitertanol), blasticidin sol (blasticidin) bromuconazole), bupirimate, butenachlor, butiochlorate, butiobate, captafol, captan, captan, carbendazim, carbendazim, chlorhydrate, carboxin, CGA 245704, quinomethionate, chlorbenzthizone Chloroneb, chlorothalonil, chlorozolinate, clozylacon, copper oxychloride, copper oxyquinolinate, copper sulfate, copper-containing compounds such as copper tallate, and bordeaux solution, cycloheximide, simoxanil (cymoxanil), cyprocona Zole, cyprodinyl (cyprodinyl), cyprofuram, debacarb (debacar b), di-2-pyridyldisnosulfide-1,1'-dioxide, dichlorofluanid, dicron (dichlone), diclobutrazol, diclomezine, Dichloran, didecyldimethylammonium chloride, dietofencarb, difenoconazole, o, o-di-iso-propyl-s-benzylthiophosphonate, dimefluazole, dimethonazole, dimethomorph, dimethomorphol ( dimethirimol), diniconazole (diniconazole), dinocap (dinocap), dipyrithione, ditarimphos (ditalimfos), dithianon, dodemorph (dodemorph), dozine (dodine), doguadine (doguadine), edifenphos (edifenphos), epoxyconazole, econazole Ethirimol, etoki Quin (ethoxyquin), ethyl (Z) -N-benzyl-N-([methyl (methyl-thioethylideneamino-oxycarbonyl) amino] thio) -p-alaninate, etridiazole (etridiazole), phenaminosulph, fenapanil ( Fenapanil), fenarimol, fenbuconazole, fenburam, fenpiclonil, fenpropidin, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fentin hydroxide, ferbam, ferimzone (ferim zone), fluazinam, fludioxonil, fluoroimide, fluquinconazole, fluquinazole, flusilazole, flutranil, flutolanil, flutriafol, folpet, feveridazole (fuberidazole), furalaxyl, furametpyr, Luconazole-cis, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imlbenconazole, ipconazole, iprobenfos, iprodione, isopropanil Butyl carbamate, isoprothiolane, kasugamycin, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methfuroxam, metiram, metirafox, metholfox metsulfovax), microbutanyl, NTNO301, neoasozin, nickel dimethyldithiocarbamate, nitrotal-isopropyl, nuarimol, offurace, organic mercury compounds, oxadixyl, oxophosphoric acid, oxycarboxine, pefurazoate (pefurazoate) ), Penconazole, pencicuron, phenazine oxide, fosetyl (phosetyl-Al), phosphorous acid, phthalide, polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb , Propamocarb hydrochloride, propiconazole, propineb, propionic acid, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyrimenoil, pyromethanil, pyroquilon, pyroxyfuron , Pyrrolenitrin, quaternary ammonium compounds, quinconazole, quinomethionate, quintoze ne, rabenazole, sodium pentachlorophenate, streptomycin, sulfur, tebuconazole, techlofthalam, technazene, tecnazene, tetraconazole, thiabendazo , Thiciofen, thifluzamide, 2- (thiocyanomethylthio) benzothiazole, thiophanatemethyl, thiram, thimibenzonazole, thioclofos-methyl, trifluanid, 1,1'-iminodi (octamethylene) diguanidine Triacetate, triadimefon, triazimenol, triazbutyl, triazoxide, tricyclazole, tridemorph, triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, XRD-563, zineb ( zineb) and ziram. The compositions of the present invention can be mixed with other rooting media to protect plants from soil, peat, or seed, from soil, or from fungal disease on leaves. . The following examples illustrate the invention. Example 1 This example illustrates the preparation of compound A. To a stirred mixture of 2-chloro-4-nitro-N, N-dimethylbenzamide (10 g) in water (200 ml) at 80 ° C. was added sodium dithionite (22.4 g). The resulting mixture was stirred at reflux for 3 hours, cooled to 50 ° C and concentrated hydrochloric acid (40ml) was added. After heating at 80 ° C. for 15 minutes, the mixture was cooled and ice (200 ml) was added at 5 ° C., followed by sodium carbonate (about 35.7 g, until pH 10). After stirring at ambient temperature for 15 minutes, the resulting precipitate was collected by filtration and washed with water (200 ml) to give 2-chloro-4-amino-N, N-dimethylbenzamide (5.1 g). Sodium methoxide (3.3 g, 0.06 mol) and xylene (20 ml) were added to a stirred mixture of xylene (50 ml) and polyethylene glycol 300 (PEG300; 0.5 ml). After 5 minutes, dry 2-chloro-4-amino-N, N-dimethylbenzamide (9.93 g) and xylene (10 ml) were added with stirring. The mixture was stirred for 10 minutes and methyl 2-fluoroisobutyrate (6.66 g) was added over 25 minutes. After further addition of xylene (10 ml), the reaction mixture was stirred at room temperature for 2.75 hours and warmed to 48-50 ° C for 0.25 hours. The reaction mixture was stirred at room temperature for 6 hours and then left overnight. The reaction mixture was then filtered to obtain a filtrate containing Compound A. Example 2 This example illustrates the preparation of Compound A. 2-Chloro-4-amino-N, N-dimethylbenzamide (2.0 g) and methyl 2-fluoroisobutyrate (1.33 g) were placed in a drying apparatus under a nitrogen atmosphere at 20 ° C. in 1,2-dimethoxyethane ( 70 ml). Sodium methoxide (0.544 g) was added quickly and the mixture was refluxed for 1.5 hours. The mixture was cooled and poured into cold aqueous hydrochloric acid (2M). The aqueous solution was extracted with ethyl acetate (twice), the combined organic extracts were washed with brine, dried (anhydrous magnesium sulfate), filtered, and the filtrate was evaporated in vacuo to leave an oil. The oil was taken up in a little diethyl ether and the solution was cooled and triturated to give a solid to which pentane was added. The resulting solid was filtered to give Compound A as a cream solid (1.992 g, 69%; mp: 133-134 ° C). Example 3 This example illustrates the preparation of compound A. A stirred mixture of 2-chloro-4-amino-N, N-dimethylbenzamide (1.0 g), potassium carbonate (700 mg) and toluene (20 ml) was refluxed until about half of the toluene was distilled off. Methyl 2-fluoroisobutyrate (650 mg) was added and the resulting mixture was refluxed for 2 hours, after which a catalytic amount of 18-crown-6 was added. After refluxing for an additional 4.5 hours, a 4 ° sieve was added. After refluxing for a further 16 hours, analysis showed that compound A was obtained in 60% yield. Example 4 This example illustrates the preparation of Compound A. To a stirred dispersion of sodium hydride in xylene (10 ml) (4.4 g of a 60% dispersion in oil previously washed with xylene (10 ml)) under a nitrogen atmosphere was added 1.0.5 g of t-amyl alcohol (10.5 g). Over 5 hours, the temperature was added while maintaining the temperature at 20-23 ° C. Additional xylene (10m) was added and the mixture was heated to 60 ° C. 2-Chloro-4-amino-N, N-dimethylbenzamide (19.85 g) was added over 7 minutes, and additional xylene (10 ml) was added. The reaction mixture was heated to 70 ° C., methyl 2-fluoroisobutyrate (13.33 g) was added over 20 minutes, and the reaction mixture was maintained at 70 ° C. for 1.75 hours, by which time the reaction mixture mass was not stirred. It became difficult. A sample of the reaction mass was filtered (overnight), the residue was slurried in water, and the pH was adjusted to 1 using dilute sulfuric acid. Extraction of the aqueous solution with diethyl ether and analysis of the ether solution by gas chromatography indicated the presence of compound A. Example 5 This example illustrates the preparation of a soluble powder formulation containing Compound A and azoxystrobin. Dry powdered compound A, azoxystrobin, POLYFON H, AEROSOL OT-B, sodium benzoate and sodium bicarbonate were mixed in a ribbon blender until a homogeneous blend was obtained. The powder blend was then dry milled through a Green-Creston UCM with a 0.25 mm screen. The ground powder was reblended in a ribbon blender for 30 minutes and then removed. POLYFON H and AEROSOL OT-B are trade names. Example 6 This example illustrates the preparation of a tank mix containing Compound A and azoxystrobin. A soluble powder containing Compound A can be prepared using the method described in Example 5 and the following components: Azoxystrobin suspension concentrates can be prepared by blending the components described in any of the following lists: Depending on the spray volume to be applied, the required amount of soluble powder containing Compound A is dispersed in water (half of the total volume used for the spray) in the spray tank. The required amount of the suspension concentrate containing azoxystrobin is then added to the mixture in the spray tank. Finally, add water to bring the spray solution to the correct volume. The contents of the spray tank are agitated throughout the process. POLYFON H, AEROSOL OT-B, BENTOPHARM B20, MORWET D425, KELZAN and PROXEL GXL are trade names. Example 7 Testing of a composition of the invention against Phytophthora infestans (fluffy mildew) on potatoes in a test area (4.5 m ² ). An aqueous solution containing compound A (200 g / ha) and azoxystrobin (125 g / ha) was applied to the test area at a rate of 300 l / ha. Seven applications were made, separated by 7-10 days, depending on the disease pressure. The illness was performed 11 days after the seventh application. On average, 9.4% of the leaf tissue was covered with fluffy mildew in the treated area, while 88.3% of the leaf tissue was covered with fluffy mildew in the untreated area.

[Procedure for Amendment] Article 184-8, Paragraph 1 of the Patent Act [Date of Submission] July 2, 1998 (1998.7.2) [Contents of Amendment] Compound A as a first active ingredient: Kresoxime-methyl, azoxystrobin, SSF126, N-methyl 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamide, famoxadone, fluazinam, 5- (4 -Fluorophenyl) -2-methoxy-5-methyl-3-phenylamino-1,3-imidazolin-4-one, 5-methyl-5- [4- (2-methyl-4-thiazolylmethoxy) phenyl ] -3-Phenylamino-1,3-oxazolidine-2,4-dione, 5- (4-fluorophenyl) -5-methyl-2-methylthio-3-phenylamino-1,3-imidazolin-4-one , 2-ethyl-5- (4-fluorophenyl) -5-methyl-3-phenylamino-1,3-imidazolin-4-one or (5S) -5-methyl-2-methylthio-5-phenyl-3 A fungicidal composition comprising -phenylamino-1,3-imidazolin-4-one; and a suitable carrier or diluent. 2. The second active ingredient according to claim 1, comprising: kresoxime-methyl, azoxystrobin, SSF126 or N-methyl 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamide. Fungicidal composition. 3. 2. The fungicidal composition according to claim 1, comprising as the second active ingredient: kresoxime-methyl or azoxystrobin. 4. 2. The fungicidal composition according to claim 1, comprising as the second active ingredient: azoxystrobin. 5. 5. A fungicidal composition according to claim 1, wherein the weight ratio of the first active ingredient to the second active ingredient is in the range from 1:10 to 10: 1. 6. 6. The fungicidal composition according to claim 1, wherein the weight ratio of the first active ingredient to the second active ingredient is in the range of 1: 7 to 2: 1. 7. A method for combating fungi comprising applying a fungicidally effective amount of the composition of claim 1 to a plant, plant seed or a plant or seed locus.

────────────────────────────────────────────────── ─── Continuation of front page    (81) Designated countries EP (AT, BE, CH, DE, DK, ES, FI, FR, GB, GR, IE, IT, L U, MC, NL, PT, SE), OA (BF, BJ, CF) , CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG), AP (GH, KE, LS, MW, S D, SZ, UG, ZW), EA (AM, AZ, BY, KG) , KZ, MD, RU, TJ, TM), AL, AM, AT , AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, F I, GB, GE, GH, HU, ID, IL, IS, JP , KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, M W, MX, NO, NZ, PL, PT, RO, RU, SD , SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, US, UZ, VN, YU, ZW (72) Inventor Foster, Nicholas Russell             Berkshire ARG             42.6 eW, Bracknell, Jerro             Tu Hill Research Station

Claims (1)

[Claims] 1. Compound A as a first active ingredient: Kresoxime-methyl, azoxystrobin, SSF126, N-methyl 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamide, famoxadone, fluazinam, 5- (4 -Fluorophenyl) -2-methoxy-5-methyl-3-phenylamino-1,3-imidazolin-4-one, 5-methyl-5- [4- (2-methyl-4-thiazolylmethoxy) phenyl ] -3-phenylamino-1,3-oxazolidine-2,4-dione, 5 (4-fluorophenyl) -5-methyl-2-methylthio-3-phenylamino-1,3-imidazolin-4-one, 2-ethyl-5- (4-fluorophenyl) -5-methyl-3-phenylamino-1,3-imidazolin-4-one or (5S) -5-methyl-2-methylthio-5-phenyl-3- A fungicidal composition comprising phenylamino-1,3-imidazolin-4-one; and a suitable carrier or diluent. 2. The fungicidal composition according to claim 1, comprising as the second active ingredient: kresoxime-methyl, azoxystrobin or fluazinam. 3. 3. The fungicidal composition according to claim 1, wherein the weight ratio of the first active ingredient to the second active ingredient is in the range of 1:10 to 10: 1. 4. A method for combating fungi comprising applying a fungicidally effective amount of the composition of claim 1 to a plant, plant seed or a plant or seed locus. 5. Compounds of formula (I): Wherein R is halogen or C _1-4 alkyl; a compound of formula (II): Is a compound of formula (III): Above. 6. The method according to claim 5, wherein the method is performed in the presence of a solvent and a surfactant. 7. 7. The method according to claim 6, wherein the surfactant is an alkoxylate or polyethylene glycol. 8. The method according to claim 5, 6 or 7, which is carried out in the presence of a base which is an alkaline earth metal or an alkali metal methoxide, carbonate, hydride or hydroxide. 9. 9. The method according to claim 8, wherein the base is sodium methoxide, potassium carbonate, sodium hydride or sodium hydroxide.