AU2005281832A1 - Fungicidal active ingredient combination - Google Patents

Description

IN THE MATTER OF an Australian Application corresponding to PCT Application PCT/EP2005/009560 RWS Group Ltd, of Europa House, Marsham Way, Gerrards Cross, Buckinghamshire; England, hereby solemnly and sincerely declares that, to the best of its knowledge and belief, the following document, prepared by one of its translators competent in the art and conversant with the English and German languages, is a true and correct translation of the PCT Application filed under No. PCT/EP2005/009560. Date: 7 March 2007 N. T. SIMPKIN Acting Deputy Managing Director For and on behalf of RWS Group Ltd - 1 Fungicidal active ingredient combination Description The present invention relates to a novel active substance combination which comprises firstly a 5 known oxime ether derivative and secondly two known triazole derivatives and which is highly suitable for controlling phytopathogenic fungi. It has already been disclosed that the oxime derivative 3-[1-[2-(4-<2-chlorophenoxy>-5 fluoropyrimid-6-yloxy)phenyl]-I-(methoximino)methyl]-5,6-dihydro-1,4,2-dioxazine (fluoxastrobin) has fungicidal properties (cf. DE-A-196 02 095). While the activity of this 10 substance is good, it leaves something to be desired in some cases at low application rates. The preparation of this compound is also disclosed in DE-A-196 02 095. It has furthermore been disclosed that the triazole derivative 3-(2,4-dichlorophenyl)-6-fluoro-2 (lH-1,2,4-triazol-1-yl)-4(3H)-quinazolinone (fluquinconazole) has fungicidal properties (cf. EP-A 183 458). While the activity of this substance is good, it leaves something to be desired in some 15 cases at low application rates. The preparation of this compound is also disclosed in EP-A-183 458. It has furthermore been disclosed that the triazole derivative 1-(4-chlorophenoxy)-3,3-dimethyl-1 (l,2,4-triazol-l-yl)butan-2-ol has fungicidal properties (cf DE-A-23 24 010). While the activity of this substance is good, it leaves something to be desired in some cases at low application rates. The 20 preparation of this compound is also disclosed in DE-A-23 24 010. It has now been found that the novel active substance combination which comprises 3-[1-[2-(4-<2 chlorophenoxy>-5-fluoropyrimid-6-yloxy)phenyl]-1-(methoximino)methyl]-5,6-dihydro-1,4,2 dioxazine, of the formula N5 N 0 0 CI F HC0 0 (fluoxastrobin) NJO 25 and (1) 3-(2,4-dichlorophenyl)-6-fluoro-2-(I H-1,2,4-triazol-I -yl)-4(3 H)-quinazolinone (reference: EP-A-183 458), of the formula -2 CI CI 0 (fluquinconazole) N N X N and (2) 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol (reference: DE-A-23 24 010), of the formula OH CI - O-CH-CH-C(CH 3

)

3 (III) N (triadimenol) N 5 N 5 has very good fungicidal properties. Surprisingly, the fungicidal activity of the active substance combination according to the invention far exceeds the total of the activities of the individual active substances. As a consequence, a true synergistic effect which could not have been predicted is present, not only a complementation of 10 activity. The active substance of the formula (I) has been disclosed (cf., for example, DE-A-196 02 095). The active substances of the formulae (II) and (III) have also been disclosed (cf. references cited). It can be seen from the structural formula for the active substance of the formula (I) that the compounds can be present as E or Z isomers. The compound (I) can therefore be present as a 15 mixture of different isomers or else in the form of a single isomer. Preferred compounds of the formula (I) are those in which the compounds of the formulae (I) and (III) are present as E isomers. It can be seen from the structural formula of the active substance of the formula (III) that the compounds have two asymmetric carbon atoms. They can therefore be present in the R or in the S form. The compounds of the formula (III) are preferably present as mixtures. 20 The active substance combination according to the invention contains the active substances of the formulae (1), (II) and (III). Additionally, it may comprise further fungicidally active components which can be admixed.

-3 When the active substances in the active substance combinations according to the invention are present in certain weight ratios, the synergistic effect becomes particularly obvious. However, the weight ratios of the active substances in the active substance combinations can be varied within a relatively wide range. 5 In general, 0.1 to 100 parts by weight, preferably 0.5 to 30 parts by weight, of active substance of the formula (II) and 0.1 to 30 parts by weight, preferably 0.5 to 15 parts by weight, of active substance of the formula 10(III) are used per part by weight of active substance of the formula (I). The active substance combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and 15 the like. Some pathogens which cause fungal and bacterial diseases and which come under the abovementioned generic terms may be mentioned by way of example, but not by limitation: Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrymans; 20 Erwinia species such as, for example, Erwinia amylovora; diseases caused by pathogens causing powdery mildew such as, for example, Blumeria species such as, for example, Blumeria graminis; Podosphaera species such as, for example, Podosphaera leucotricha; Sphaerotheca species such as, for example, Sphaerotheca fuliginea; 25 Uncinula species such as, for example, Uncinula necator; diseases caused by pathogens causing rust diseases such as, for example, Gymnosporangium species such as, for example, Gymnosporangium sabinae -4 Hemileia species such as, for example, Hemileia vastatrix; Phakopsora species such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species such as, for example, Puccinia recondita; Uromyces species such as, for example, Uromyces appendiculatus; 5 diseases caused by pathogens from the Oomycetes group such as, for example, Bremia species such as, for example, Bremia lactucae; Peronospora species such as, for example, Peronospora pisi or P. brassicae; Phytophthora species such as, for example, Phytophthora infestans; Plasmopara species such as, for example, Plasmopara viticola; 10 Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species such as, for example, Pythium ultimum; leaf spot diseases and foliar wilts caused by, for example, Alternaria species such as, for example, Alternaria solani; 15 Cercospora species such as, for example, Cercospora beticola; Cladiosporum species such as, for example, Cladiosporium cucumerinum; Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium); Colletotrichum species such as, for example, Colletotrichum lindemuthanium; 20 Cycloconium species such as, for example, Cycloconium oleaginum; Diaporthe species such as, for example, Diaporthe citri; Elsinoe species such as, for example, Elsinoe fawcettii; Gloeosporium species such as, for example, Gloeosporium laeticolor; - 5 Glomerella species such as, for example, Glomerella cingulata; Guignardia species such as, for example, Guignardia bidwelli; Leptosphaeria species such as, for example, Leptosphaeria maculans; Magnaporthe species such as, for example, Magnaporthe grisea; 5 Mycosphaerella species such as, for example, Mycosphaerelle graminicola; Phaeosphaeria species such as, for example, Phaeosphaeria nodorum; Pyrenophora species such as, for example, Pyrenophora teres; Ramulania species such as, for example, Ramularia collo-cygni; Rhynchosporium species such as, for example, Rhynchosporium secalis; 10 Septoria species such as, for example, Septoria apii; Typhula species such as, for example, Typhula incarnata; Venturia species such as, for example, Venturia inaequalis; root and stem diseases caused by, for example, Corticium species such as, for example, Corticium graminearum; 15 Fusarium species such as, for example, Fusarium oxysporum; Gaeumannomyces species such as, for example, Gaeumannomyces graminis; Rhizoctonia species such as, for example, Rhizoctonia solani; Tapesia species such as, for example, Tapesia acuformis; Thielaviopsis species such as, for example, Thielaviopsis basicola; 20 ear and panicle diseases (including maize cobs), caused by, for example, Alternaria species such as, for example, Alternaria spp.; Aspergillus species such as, for example, Aspergillus flavus; Cladosporium species such as, for example, Cladosporium spp.; -6 Claviceps species such as, for example, Claviceps purpurea; Fusarium species such as, for example, Fusarium culmorum; Gibberella species such as, for example, Gibberella zeae; Monographella species such as, for example, Monographella nivalis; 5 diseases caused by smut fungi such as, for example, Sphacelotheca species such as, for example, Sphacelotheca reiliana; Tilletia species such as, for example, Tilletia caries; Urocystis species such as, for example, Urocystis occulta; Ustilago species such as, for example, Ustilago nuda; 10 fruit rot caused by, for example, Aspergillus species such as, for example, Aspergillus flavus; Botrytis species such as, for example, Botrytis cinerea; Penicillium species such as, for example, Penicillium expansum; Sclerotinia species such as, for example, Sclerotinia sclerotiorum; 15 Verticilium species such as, for example, Verticilium alboatrum; seed- and soil-borne rots and wilts, and seedling diseases, caused by, for example, Fusarium species such as, for example, Fusarium culmorum; Phytophthora species such as, for example, Phytophthora cactorum; Pythium species such as, for example, Pythium ultimum; 20 Rhizoctonia species such as, for example, Rhizoctonia solani; Sclerotium species such as, for example, Sclerotium rolfsii; cankers, galls and witches' brooms, caused by, for example, Nectria species such as, for example, Nectria galligena; -7 wilting diseases caused by, for example, Monilinia species such as, for example, Monilinia laxa; deformations of leaves, flowers and fruits, caused by, for example, Taphrina species such as, for example, Taphrina deformans; 5 degenerative diseases of woody species, caused by, for example, Esca species such as, for example, Phaemoniella clamydospora; flower and seed diseases caused by, for example, Botrytis species such as, for example, Botrytis cinerea; diseases of plant tubers caused by, for example, 10 Rhizoctonia species such as, for example, Rhizoctonia solani; The active substance combination according to the invention is particularly suitable for controlling cereal diseases such as Erysiphe, Cochliobolus, Pyrenophora, Rhynchosporium, Septoria, Fusarium, Pseudocercosporella, Leptosphaeria and Pyricularia and for controlling fungal infestation of non-cereal crops such as grapevines, fruit, peanut, vegetable, for example 15 Phythophthora, Plasmopara, Pythium, and powdery mildews such as, for example, Sphaerotheca or Uncinula, and leaf spot pathogens such as Venturia, Alternaria and Septoria and also Rhizoctonia, Botrytis, Sclerotinia and Sclerotium. The good plant tolerance of the active substance combinations, at the concentrations required for controlling plant diseases, permits a treatment of aerial plant parts, of vegetative propagation 20 material and of seed, and of the soil. The active substance combinations according to the invention can be employed for foliar application or else as seed-dressing materials. The active substance combinations according to the invention are also suitable for increasing the yield. Moreover, they show a low degree of toxicity and are well tolerated by plants. All plants and plant parts can be treated in accordance with the invention. Plants are understood as 25 meaning, in the present context, all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant varieties capable or not capable of being protected by Plant -8 Breeders' Rights. Plant parts are understood as meaning all aerial and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative 5 propagation material, for example cuttings, tubers, rhizomes, slips and seeds. As already mentioned above, all plants and their parts can be treated in accordance with the invention. In a preferred embodiment, plant species and plant varieties which are found in the wild or are obtained by traditional biological breeding methods, such as hybridization or protoplast fusion, and parts of the former are treated. In a further preferred embodiment, transgenic plants and 10 plant varieties which have been obtained by recombinant methods, if appropriate in combination with traditional methods (genetically modified organisms) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" has been illustrated above. Particularly preferably, plants of the plant cultivars which are in each case commercially available 15 or in use are treated according to the invention. Plant cultivars are understood as meaning plants with new properties ("traits") which have been obtained by conventional cultivation, by mutagenesis or else by recombinant DNA techniques. These may be cultivars, biotypes or genotypes. 20 Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or extensions of the activity spectrum and/or an increase in the activity of the substances and compositions that can be used according to the invention, better plant growth, increased tolerance 25 to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated maturation, higher yields, better quality and/or a higher nutritional value of the harvested products, better storage ability and/or processability of the harvested products which exceed the effects which were actually to be expected are possible. 30 The preferred transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are to be treated according to the invention include all plants which, as a result of the recombinant modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, 35 increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated maturation, higher yields, better quality and/or a higher nutritional value of the harvested products, better storage ability -9 and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active substances. Examples of transgenic plants which may be 5 mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasized in particular are increased defence of the plants against insects as a result of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus 10 Thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits which are also particularly emphasized are the increased defence of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and the correspondingly expressed proteins and toxins. Traits that are 15 furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active substances, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and 20 potato varieties which are sold under the trade names YIELD GARD@ (for example maize, cotton, soya beans), KnockOut@ (for example maize), StarLink@ (for example maize), Bollgard@ (cotton), Nucoton@ (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosates, for example maize, cotton, 25 soya beans), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI@ (tolerance to imidazolinones) and STS@ (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned also include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant varieties which will be developed, or reach the 30 market, in the future and which have these genetic traits or have genetic traits yet to be developed. The plants which have been detailed can particularly advantageously be treated according to the invention with the active substance mixtures according to the invention. The preferred ranges stated hereinabove for the active substances or mixtures also apply to the treatment of these plants. The treatment of plants with the mixtures which are specifically mentioned in the present text may 35 be particularly emphasized.

- 10 The treatment according to the invention with the active substances, of the plants and plant parts, is carried out directly or by acting on their environment, habitat, or store by the customary treatment methods, for example by immersion, spraying, vaporizing, fogging, broadcasting, painting on and, in the case of propagation material, in particular in the case of seeds, furthermore 5 by coating with one or more coats. The active substance combinations according to the invention can be converted into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsulations in polymeric substances and in coating compositions for seed, and ULV formulations. 10 These formulations are produced in a known manner, for example by mixing the active substances or active substance combinations with extenders, that is, liquid solvents, pressurized liquefied gases and/or solid carriers, optionally with the use of surface-active agents, that is emulsifers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ for example organic solvents as cosolvents. Suitable liquid solvents are essentially: aromatics, such as 15 xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and 20 also water. Liquefied gaseous extenders or carriers are those liquids which are gaseous at ambient temperature and at atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. As solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for 25 granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. As emulsifiers and/or foam formers there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl 30 polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates. As dispersants there are suitable: for example lignin-sulphite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as 35 natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.

- 11 It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, 5 molybdenum and zinc. The formulations in general contain between 0.1 and 95% by weight of active substance, preferably between 0.5 and 90%. 10 The active substance combinations according to the invention, as such or in their formulations, can also be used as a mixture with known fungicides, bactericides, acaricides, nematicides, or insecticides, for example, to improve the activity spectrum or prevent the development of resistance. In many instances, synergistic effects are obtained, i.e. the activity of the mixture exceeds the activity of the individual components. 15 Fungicides: 1. Nucleic acid synthesis inhibitors benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, 20 hymexazol, metalaxyl-M, ofurace, oxadixyl, oxolinic acid 2. Mitosis and cell division inhibitors benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate methyl, zoxamide 25 3. Respiration inhibitors 3.1. complex I diflumetorim 30 3.2. complex II boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad, thifluzamide 3.3. complex III 35 azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin - 12 3.4. Decouplers dinocap, fluazinam 3.5. ATP production inhibitors 5 fentin acetate, fentin chloride, fentin hydroxide, silthiofam 4. Amino acid and protein biosynthesis inhibitors andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil 10 5. Signal transduction inhibitors fenpiclonil, fludioxonil, quinoxyfen 6. Lipid and membrane synthesis inhibitors 15 chlozolinate, iprodione, procymidone, vinclozolin pyrazophos, edifenphos, iprobenfos (IBP), isoprothiolan tolclofos-methyl, biphenyl iodocarb, propamocarb, propamocarb hydrochloride 20 7. Ergosterol biosynthesis inhibitors fenhexamid, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, 25 metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, imazalil, imazalil sulphate, oxpoconazole, fenarimol, flurprimidole, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidine, 30 spiroxamine, naftifin, pyributicarb, terbinafin 8. Cell wall synthesis inhibitors benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, 35 validamycin A - 13 9. Melanin biosynthesis inhibitors carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole 10. Resistance induction 5 acibenzolar-S-methyl, probenazole, tiadinil 11. Multi-site captafol, captan, chlorothalonil, copper salts such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, dichlofluanid, 10 dithianon, dodine, dodine free base, ferbam, fluorofolpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulphur and sulphur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram 12. Unknown 15 amibromdol, benthiazole, bethoxazin, capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulphate, irumamycin, methasulphocarb, metrafenon, methyl isothiocyanate, mildiomycin, natamycin, nickel 20 dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, 2-phenylphenol and salts, piperalin, propanosine-sodium, proquinazid, pyrrolnitrine, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4-(methylsul fonyl)pyridine, N-(4-chloro-2-nitrophenyl)-N-ethyl-4 methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N-(2,3 25 dihydro-1,1,3-trimethyl-l H-inden-4-yl)-3-pyridinecarboxamide, 3-[5-(4-chlorophenyl)-2,3 dimethylisoxazolidin-3-yl]pyridine, cis- 1 -(4-chlorophenyl)-2-(l H-1,2,4-triazol- I -yl)cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3 (trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl] -3H- 1,2,3-triazol-3-one (185336-79 2), methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-IH-imidazole-5-carboxylate, 3,4,5 30 trichloro-2,6-pyridinecarbonitrile, methyl-2-[[[cyclopropyl[(4-methoxy phenyl)imino]methyl ]thio]methyl]-.alpha.-(methoxymethylene)benzacetate, 4-chloro-alpha propynyloxy-N-[2-[3 -methoxy-4-(2-propynyloxy)phenyl]ethyl]benzacetamide, (2S)-N-[2-[4-[[3-(4 chlorophenyl)-2-propynyl ]oxy]-3 -methoxyphenyl]ethyl] -3 -methyl-2-[(methylsul fonyl)amino] butanamide, 5-chloro-7-(4-methylpiperidine-1-yl)-6-(2,4,6-trifluorophenyl)(1,2,4]triazolo[1,5-a] 35 pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-N-[(lR)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5 a]pyrimidin-7-amine, 5-chloro-N-[(IR)-1,2-dimethylpropyl]-6-(2,4,6 trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, N-[ I -(5-bromo-3-chloropyridin-2- - 14 yl)ethyl]-2,4-dichloronicotinamide, N-(5-bromo-3-chlorpyridin-2-yl)methyl-2,4 dichloronicotinamide, 2-butoxy-6-iodo-3-propylbenzopyranon-4-one, N- {(Z) [(cyclopropylmethoxy)imino] [6-(difluoromethoxy)-2,3-difluorophenyl]methyl} -2-benzacetamide, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide, 2-[[[[1-[3(1-fluoro-2 5 phenylethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alpha-E benzacetamide, N- (2-[3 -chloro-5 -(trifluoromethyl)pyridin-2-yl]ethyl} -2 (trifluoromethyl)benzamide, N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl I H-pyrazole-4-carboxamide, N-(6-methoxy-3-pyridinyl)cyclopropane carboxamide, 1-[(4 methoxyphenoxy)methyl]-2,2-dimethylpropyl-IH-imidazole-1-carboxylic acid, 0-[l-[(4-methoxy 10 phenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioic acid, 2-(2-{[6-(3-chloro-2 methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide Bactericides: Bronopol, dichlorophen, nitrapyrin, nickel dimethyl dithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and 15 other copper preparations. Insecticides/Acaricides/Nematicides: 1. Acetylcholine esterase (AChE) inhibitors 1.1 Carbamates (for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethi 20 phos, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb) 25 1.2 Organophosphates (for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, 30 dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl 0-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, 35 omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, -15 quinalphos, sebufos, sulfotep, suiprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion) 2. Sodium channel modulators/voltage-dependent sodium channel blockers 5 2.1 Pyrethroids (for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopernethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyflu thrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fen 10 valerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethnin (cis-, trans-), phenothrin (IR trans-isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (lR isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)) 15 2.2 Oxadiazines (for example indoxacarb) 3. Acetylcholine receptor agonists/antagonists 3.1 Chloronicotinyls/neonicotinoids (for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam) 20 3.2 Nicotine, bensultap, cartap 4. Acetylcholine receptor modulators 4.1 Spinosyns (for example spinosad) 25 5. GABA-controlled chloride channel antagonists 5.1 Cyclodiene organochlorines (for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor 5.2 Fiprols (for example acetoprole, ethiprole, fipronil, vaniliprole) 30 6. Chloride channel activators 6.1 Mectins (for example abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin) 7. Juvenile hormone mimetics 35 (for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene) -16 8. Ecdysone agonists/disruptors 8.1 Diacylhydrazines (for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide) 9. Chitin biosynthesis inhibitors 5 9.1 Benzoylureas (for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron) 9.2 Buprofezin 9.3 Cyromazine 10 10. Inhibitors of oxidative phosphorylation, ATP disruptors 10.1 Diafenthiuron 10.2 Organotins (for example azocyclotin, cyhexatin, fenbutatin oxide) 15 11. Uncouplers of oxidative phosphorylation by interrupting the H-proton gradient 11.1 Pyrroles (for example chlorfenapyr) 11.2 Dinitrophenols (for example binapacyrl, dinobuton, dinocap, DNOC) 12. Site-I electron transport inhibitors 20 12.1 METIs (for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad) 12.2 Hydramethylnon 12.3 Dicofol 25 13. Site-If electron transport inhibitors 13.1 Rotenone 14. Site-III electron transport inhibitors 14.1 Acequinocyl, fluacrypyrim 30 15. Microbial disruptors of the insect gut membrane Bacillus thuringiensis strains 16. Fat biosynthesis inhibitors 35 16.1 Tetronic acids (for example spirodiclofen, spiromesifen) 16.2 Tetramic acids [for example 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3 en-4-yl ethyl carbonate (also known as: carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l- - 17 azaspiro[4.5]dec-3-en-4-yl ethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid, cis-3-(2,5 dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS Reg.-No.: 203313-25-1)] 5 17. Carboxamides (for example flonicamid) 18. Octopaminergic agonists (for example amitraz) 10 19. Inhibitors of magnesium-stimulated A TPase (for example propargite) 20. Phthalamides 15 (for example N 2 -[1,1-dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N'-[2-methyl-4-[1,2,2,2 tetrafluoro-l-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide (CAS Reg.-No.: 272451 65-7), flubendiamide) 21. Nereistoxin analogues 20 (for example thiocyclam hydrogen oxalate, thiosultap sodium) 22. Biologicals, hormones or pheromones (for example azadirachtin, Bacillus spec., Beauveria spec., codlemone, Metarrhizium spec., Paecilomyces spec., thuringiensin, Verticillium spec.) 25 23. Active substances with unknown or unspecific mechanisms of action 23.1 Fumigants (for example aluminium phosphide, methyl bromide, sulfuryl fluoride) 23.2 Selective antifeedants (for example cryolite, flonicamid, pymetrozine) 23.3 Mite growth inhibitors (for example clofentezine, etoxazole, hexythiazox) 30 23.4 Amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quino methionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnon, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyrafluprole, pyridalyl, pyriprole, sulfluramid, tetradifon, tetrasul, triarathene, verbutin, 35 furthermore the compound 3-methylphenyl propylcarbamate (tsumacide Z), the compound 3-(5-chloro 3-pyndinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1 ]octane-3-carbonitrile (CAS Reg. No. 185982-80 3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (cf. WO 96/37494, WO - 18 98/25923), and preparations which contain insecticidally active plant extracts, nematodes, fungi or viruses. A mixture with other known active substances such as herbicides, safeners, or semiochemicals, or with fertilizers and growth regulators is also possible. 5 The compounds (I), (II) and (III) can be applied either simultaneously, which means jointly or separately, or else in succession, the sequence, in the case of separate application, generally having no effect on the result of the control measure. The active substance combinations can be applied as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, 10 emulsions, suspensions, wettable powders, soluble powders and granules. They are applied in the customary manner, for example by drenching, spraying, atomizing, broadcasting, brushing on, as a dry seed treatment, as a solution for seed treatment, a water-soluble powder for seed treatment or a water-dispersible powder for the slurry treatment of seed, or by encrusting. When employing the active substance combinations according to the invention, the application 15 rates can be varied within a substantial range, depending on the type of application. In the treatment of plant parts, the application rates of active substance combination are generally between 0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha. For the treatment of seed, the application rates of active substance combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For treating the soil, the 20 application rates of active substance combination are generally between 0.1 and 10 000 g/ha, preferably between I and 5000 g/ha. The good fungicidal activity of the active substance combinations according to the invention can be seen from the examples which follow. While the fungicidal activity of the individual active substances shows weaknesses, the combinations have an activity which exceeds a simple 25 summation of activities. In fungicides, a synergistic effect is always present when the fungicidal activity of the active substance combinations exceeds the total of the activities of the active substances when applied individually. The expected activity for a given combination of 2 or 3 active substances can be calculated as 30 follows as described by S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22): If - 19 X is the efficacy when employing active substance A at an application rate of rn ppm, Y is the efficacy when employing active substance B at an application rate of n ppm, Z is the efficacy when employing active substance C at an application rate of r ppm, El is the efficacy when employing the active substances A and B at application rates of m and 5 n ppm and

E

2 is the efficacy when employing the active substances A and B and C at application rates of m and n and r ppm, then X - Y E, = X +Y 100 10 and for a combination of 3 active substances: X.Y-X.Z-Y.Z X -Y.Z

E

2 = X +Y +Z- ______+ __ 100 10000 In this formula, the efficacy is determined in %. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease has been observed. If the actual fungicidal effect exceeds the calculated value, then the activity of the combination is 15 superadditive, i.e. a synergise is present. In this case, the actually observed efficacy must exceed the value calculated with the above formula for the expected efficacies E, and E 2 . The invention is illustrated by the examples which follow. However, the invention is not limited to the examples.

- 20 Example Pyricularia oryzae test (in vitro) / microtitre plates The microtest is carried out in microtitre plates using potato dextrose broth (PDB) as liquid experimental medium. The active substances are applied as technical-grade a.i., dissolved in acetone. 5 A spore suspension of Pyricularia oryzae is used for the inoculation. After three days' incubation in the dark and with shaking (10 Hrz), the transparency of each filled cavity of the microtitre plates is determined with the aid of a spectrophotometer. In this context, 0% means an efficacy which corresponds to the growth in the controls, while an efficacy of 100% means that no fungal growth is observed. 10 It can be seen clearly from the table which follows that the found activity of the active substance combination according to the invention exceeds the calculated value, i.e. synergism is present.

-21 TABLE Pyricularia oryzae test (in vitro) / microtest Active substance Application rate of % efficacy active substance in ppm Known: (I) fluoxastrobin 134 (II) fluquinconazole 1 23 (III) triadimenol 1 7 Mixture according to the invention: Mixing ratio Application rate of Actual efficacy Expected value active substance in calculated using ppm Colby's formula (+ (H) + (I) 1:1:1 1+1+1 87 56

Claims (10)

1. Active substance combination, comprising a compound of the formula N ' N 0 0 CI FC :N - (fluoxastrobin) NJO and (1) a compound of the formula CI CI 0 F (JJ) N (fluquinconazole) N N N'N 5 N and (2) a compound of the formula OH CI O-CH-CH-C(CH 3 ) 3 , N (triadimenol) N /

2. Active substance combination according to Claim 1, characterized in that, in the active substance combination, the weight ratio of active substance of the formula (I) to -active substance of the formula (II) is 1:0.1 to 1:100, and to - active substance of the formula (III) 1:0.1 to 1:30.

3. Method of controlling phytopathogenic fungi, characterized in that an active substance combination as defined in Claim 1 or 2 is allowed to act on the fungi and/or their - 23 environment or on the plants, plant parts, seeds, soils, areas, materials or spaces to be kept free from them.

4. Method according to Claim 3, characterized in that the compound (I) according to Claim 1, the compound (II) according to Claim 1 and the compound (III) according to Claim I are applied simultaneously together or separately or in succession.

5. Propagation material coated with an active substance combination according to one or more of Claims I to 4.

6. Fungicidal compositions containing a content of an active substance combination as defined in Claim 1.

7. Use of the active substance combination or compositions as defined in Claims 1, 2 and 6 for controlling fungi.

8. Method for the preparation of fungicidal compositions, characterized in that an active substance combination according to Claim 1 is mixed with extenders and/or surface-active substances.

9. Use of active substance combinations according to Claim 1 for treating transgenic plants.

10. Use of active substance combinations according to Claim I for treating seed of transgenic plants.