WO2006027209A1

WO2006027209A1 - Fungicidal active ingredient combination

Info

Publication number: WO2006027209A1
Application number: PCT/EP2005/009560
Authority: WO
Inventors: Anne Suty-Heinze; Markus Heldt; Burkhard SCHÜTZ; Peter Dahmen
Original assignee: Bayer Cropscience Ag
Priority date: 2004-09-10
Filing date: 2005-09-06
Publication date: 2006-03-16
Also published as: NZ553660A; AU2005281832A1; ZA200701934B; DE102004043819A1; EP1791429A1

Abstract

The invention relates to a novel combination of active ingredients, which contains one previously known oxime ether derivative and two previously known triazol-derivatives and which is highly suitable for controlling phytopathogenic fungi.

Description

Fungicidal combination of active ingredients

description

The present invention relates to a novel active ingredient combination which contains a known oxime ether derivative on the one hand and two known triazole derivatives on the other hand and is very well suited for controlling phytopathogenic fungi.

It is already known that the oxime derivative is 3- [1- [2- (4- <2-chlorophenoxy> 5-fluoropyrimidin-6-yloxy) -phenyl] -1- (methoximino) -methyl] -5 , 6-dihydro-1,4,2-dioxazine (fluoxastrobin) has fungicidal properties (see DE-A-196 02 095). The effectiveness of this substance is good, but it leaves little to be desired at low application rates in some cases. The preparation of this compound is likewise known from DE-A-196 02 095.

It is further known that the triazole derivative is 3- (2,4-dichlorophenyl) -6-fluoro-2- (1H-1,2,4-triazol-1-yl) -4 (3H) -quinazolinone (fluquinconazole ) has fungicidal properties (see EP-A-183458). The effectiveness of this substance is good; However, at low application rates, it leaves something to be desired in some cases. The preparation of this compound is also known from EP-A-183 458.

It is also known that the triazole derivative is 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-ol fungicidal properties has (see DE-A-23 24010). The effectiveness of this substance is good; However, at low application rates, it leaves something to be desired in some cases. The preparation of this compound is also known from DE-A-2324 010.

It has now been found that the new combination of active ingredients, the 3- [1- [2- (4- <2-chlorophenoxy) -5-fluoropyrimid-6-yloxy) -phenyl] -1- (methoximino) -methyl] - 5,6-dihydro-1,4,2-dioxazine of the formula

and

(1) 3- (2,4-dichlorophenyl) -6-fluoro-2- (1H-1,2,4-triazoM -yl) -4 (3H) -quinazolinone (Reference: EP-A-183 458) the formula

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

(Triadinenol)

contains very good fungicidal properties.

Surprisingly, the fungicidal activity of the invention Active substance combination significantly higher than the sum of the effects of the individual active ingredients. So there is an unpredictable, true synergistic effect and not just an effect supplement.

The active ingredient of the formula (I) is known (cf., for example, DE-A-196 02 095). The active compounds of the formulas (II) and (III) are likewise known (see the references given).

From the structural formula for the active ingredient of the formula (I) it can be seen that the compounds can be present as E or Z isomer. The compound (I) can therefore be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (I) in which the compounds of the formulas (I) and (III) are present as E isomers.

From the structural formula for the active ingredient of formula (III) it can be seen 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.

The active ingredient combination according to the invention contains the active compounds of the formulas (I), (II) and (III). It can also contain other fungicidal Zumischkomponenten beyond.

If the active ingredients in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active ingredients in the drug combinations can be varied within a relatively wide range. In general, 1 part by weight of active compound of the formula (I)

0.1 to 100 parts by weight, preferably 0.5 to 30 parts by weight of active compound of the formula (II), and

0.1 to 30 parts by weight, preferably 0.5 to 15 parts by weight of active compound of the formula (III).

The active compound combinations according to the invention have very good fungicidal properties and can be used for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.

By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-enumerated generic terms, are named:

Xanthomonas species, such as Xanthomonas campestris pv. Oryzae;

Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora;

Diseases caused by powdery mildews such as e.g. Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;

Diseases caused by pathogens of rust diseases such as Gymnosporangium species, such as Gymnosporangium sabinae Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi and

Phakopsora meibomiae;

Puccinia species, such as Puccinia recondita;

Uromyces species, such as Uromyces appendiculatus;

Diseases caused by pathogens of the group of Oomycetes, e.g.

Bremia species, such as Bremia lactucae;

Peronospora species such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans;

Plasmopara species, such as Plasmopara viticola;

Pseudoperonospora species, such as Pseudoperonospora humuli or

Pseudoperonospora cubensis; Pythium species such as Pythium ultimum;

Leaf spot diseases and leaf wilt caused by e.g.

Alternaria species, such as Alternaria solani;

Cercospora species, such as Cercospora beticola; Cladiosporum species, such as Cladiosporium cucumerinum;

Cochliobolus species, such as Cochliobolus sativus

(Conidia form: Drechslera, Syn: Helminthosporium);

Colletotrichum species, such as Colletotrichum lindemuthanium;

Cycloconium species such as cycloconium oleaginum; Diaporthe species, such as Diaporthe citri;

Elsinoe species, such as Elsinoe fawcettii;

Gloeosporium species, such as, for example, Gloeosporium laeticolor;

Glomerella species, such as Glomerella cingulata;

Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans;

Magnaporthe species, such as Magnaporthe grisea;

Mycosphaerella species, such as Mycosphaerelle graminicola;

Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as, for example, Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis;

Root and stem diseases caused by e.g.

Corticium species, such as Corticium graminearum; Fusarium species such as Fusarium oxysporum;

Gaeumannomyces species such as Gaeumannomyces graminis;

Rhizoctonia species, such as Rhizoctonia solani;

Tapesia species, such as Tapesia acuformis;

Thielaviopsis species, such as Thielaviopsis basicola; Ear and panicle diseases (including corncob) caused by e.g.

Alternaria species such as Alternaria spp .;

Aspergillus species, such as Aspergillus flavus;

Cladosporium species such as Cladosporium spp .; Claviceps species, such as Claviceps purpurea;

Fusarium species such as Fusarium culmorum;

Gibberella species, such as Gibberella zeae;

Monographella species, such as Monographella nivalis;

Diseases caused by fire fungi, e.g.

Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries; Urocystis species, such as Urocystis occulta; Ustilago species such as Ustilago nuda;

Fruit rot caused, for example, by Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species such as Penicillium expansum; Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species such as Verticilium alboatrum;

Seed and soil-borne rots and wilting, as well

Seedling diseases caused by e.g.

Fusarium species such as Fusarium culmorum;

Phytophthora species, such as Phytophthora cactorum;

Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani;

Sclerotium species, such as Sclerotium rolfsii;

Cancers, galls and witches brooms caused by e.g. Nectria species, such as Nectria galligena;

Wilt diseases caused by e.g. Monilinia species, such as Monilinia laxa;

Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, such as Taphrina deformans;

Degenerative diseases of woody plants, caused by e.g. Esca species, such as Phaemoniella clamydospora;

Flower and seed diseases caused by e.g. Botrytis species, such as Botrytis cinerea;

Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani;

The combination of active substances according to the invention is particularly suitable for combating cereal diseases, such as Erysiphe, Cochliobolus, Pyrenophora, Rhynchosporium, Septoria, Fusarium, Pseudocercosporella, Leptosphaeria and Pyricularia and for combating fungal infestations on non-cereal crops such as wine, fruit, peanut, vegetables, for example Phythophthora, Plasmopara, Pythium and powdery mildews such as Sphaerotheca or Uncinula and leaf spot exciters such as Venturia, 5 Alternaria and Septoria and Rhizoctonia, Botrytis, Sclerotinia and Sclerotium.

The good plant compatibility of the active ingredient combinations in the concentrations necessary for controlling plant diseases allows treatment of aboveground plant parts, of planting and seed, and of the soil. The active compound combinations according to the invention can be used for foliar application or as a mordant.

The active compound combinations according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety protection rights. Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, o stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes , The plant parts also include crops as well as vegetative and generative propagation material, For example, cuttings, tubers, rhizomes, offshoots and seeds.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.

Can, depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet) by The inventive treatment also result in superadditive ( "synergistic ¹¹⁾ effects. For example, reduced application rates and / or extensions of the activity spectrum and / or Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects. 60

- 10 -

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soy, potato, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, potato, cotton and rapeseed should be highlighted. Traits which are particularly emphasized are the increased defense of the plants against insects by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CrylllB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter "Bt plants"). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are further emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example Imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), (MI® (tolerance against imidazolinone) and STS® (tolerance to sulphonylureas, eg maize) The herbicide-resistant plants (grown conventionally for herbicide-tolerance) also include the varieties sold under the name Clearfield® (eg maize) in the future developed or future on the market coming plant varieties with these or future developed genetic traits ("Traits").

The listed plants can be treated particularly advantageously according to the invention with the active substance mixtures according to the invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the mixtures specifically mentioned in the present text.

The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing and propagating material, in particular in the case of seeds single or multi-layer coating. The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV formulations.

These formulations are prepared in a known manner, for example by mixing the active compounds or the active compound combinations with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or or foaming agents. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as 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 petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants, such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: 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 granules are: for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifying and / or foam-forming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers,

Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates. Suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 and 95% by weight of active ingredients, preferably between 0.5 and 90%.

The active compound combinations according to the invention can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, for example in order to broaden the activity spectrum or to prevent development of resistance. In many cases, one obtains synergistic effects, ie the effectiveness of the mixture is greater than the effectiveness of the Individual components.

fungicides:

1. Inhibition of nucleic acid synthesis

Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl-M, ofurace, oxadixyl, oxolinic acid

2. Inhibition of mitosis and cell division

Benomyl, Carbendazim, Diethofencarb, Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide

3. Inhibition of the Respiratory Chain 3.1 Complex I Diflumetorim

3.2 Complex Il

Boscalid, Carboxin, Fenfuram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide

3.3 Complex III

Azoxystrobin, Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Picoxystrobin

3.4 Decoupler Dinocap, Fluazinam

3.5 Inhibition of A TP production

Fentin acetate, fentin chloride, fentin hydroxide, silthiofam 4. Inhibition of amino acid and protein biosynthesis

Andoprim, blasticidin-S, cyprodinil, kasugamycin,

Kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil

5. Inhibition of signal transduction fenpiclonil, fludioxonil, quinoxyfen

6. Inhibition of fat and membrane synthesis chlozolinate, iprodione, procymidone, vinclozolin pyrazophos, edifenphos, lprobenfos (IBP), isoprothiolane tolclofos-methyl, biphenyl iodocarb, propamocarb, propamocarb hydrochloride

7. Inhibition of ergosterol biosynthesis fenhexamid,

Azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil, Imazalilsulfat, Oxpocoπazol, Fenarimol, Flurprimidol, Nuarimol, Pyrifenox, Triforin, Pefurazoate, Prochloraz, Triflumizol, Viniconazole, Aldimorph, Dodemorph, Dodemorphacetat, Fenpropimorph, tridemorph, fenpropidin, spiroxamine, naftifine, pyributicarb, terbinafm

8. Inhibition of Cell Wall Synthesis Benthiavalicarb, Bialaphos, Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A 9. Inhibition of melanin biosynthesis

Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole

10. Resistance Induction Acibenzolar-S-methyl, Probenazol, Tiadinil

11. MultiSite

Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and bordeaux mixture, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, guazatine, guazatin acetate, iminoctadine, iminoctadinalesilate, iminoctadine triacetate, Mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram

12. Unknown

Amibromdole, benthiazole, bethoxazine, 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 sulfate, irumamycin, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl.octhilinone, oxamocarb, oxyfenthiine, pentachlorophenol and salts, 2-phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrrolnitrin , Quintozen, Tecloftalam, Tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methyl benzene sulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1, 1, 3-trimethyl-1H-inden-4-yl) - 3-pyridinecarboxamide, 3- [5- (4-chloro-phenyl) -2,3-dimethylisoxazolidin-3-yl] pyrene din, cis-1 - (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-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) -1H-imidazole-5-carboxylate, 3, 4,5-trichloro-2,6-pyridine-dicarbonitrile, methyl 2 - [[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] -. Alpha.

(methoxymethylene) benzoacetate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-

5 4- (2-propynyl-oxy) -phenyl] -ethyl] -benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] ~ 3-methyl-2

[(methylsulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a ] pyrimidine, 5-chloro-6- (2,4,6-trifluorophenyl) -N - [(1R) -1, 2,2-trimethylpropyl] [1,2,4] triazolo [1,5-a] pyrimidine-o-7-amine, δ-chloro-N-> IRVI-dimethyl-dimethyl-e1-ce, e-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7-amine, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinotin, 2- Butoxy-6-iodo-3-propyl-benzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2- 5 -benzacetamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2 - [[[[[1- [3 (1-fluoro-2-phenylethyl) oxy] phenyl] ethylidene ] amino] oxy] methyl] -alpha (methoxyimino) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl ) benzamide, N- (3 ', 4 ^l -dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-o 1 H -pyrazole-4-carboxamide, N -fβ -Methoxy-S-pyridinyl O-cyclopropane carboxamide, 1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, O- [1 - [(4-methoxyphenoxy) 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 5

bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. 0

Insecticides / acaricides / nematicides:

1. Acetylcholinesterase (AChE) inhibitors

1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxime, 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)

1.2 Organophosphates (eg 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, dialifos, diazinon, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, Fenitrothion, Fensulfothione, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathione, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate , Oxydemeton-methyl, parathion (-methyl / -ethyl), phenthoates, phorates, phosalones, phosmet, phosphamidone, phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propaphos, propeta mphos, prothiofos, prothoates, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion)

2. Sodium Channel Modulators / Voltage Dependent Sodium Channel Blockers 2.1 Pyrethroids (eg, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin , Biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, Cyfluthrin, cyhalothrin, cypermethrin (alpha, beta, theta, zeta), cyphenothrin, DDT, deltamethrin, empenthrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, Flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis, trans), phenothrin (1R-trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, Silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (1R-isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum)) 2.2 oxadiazines (eg indoxacarb)

3. Acetylcholine receptor agonists / antagonists

3.1 chloronicotinyls / neonicotinoids (e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam)

3.2 Nicotine, Bensultap, Cartap

4. Acetylcholine Receptor Modulator 4.1 Spinosyn (e.g., Spinosad)

5. GABA-driven chloride channel antagonists

5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor

5.2 Fiproles (e.g., acetoprole, ethiprole, fipronil, vaniliprole)

6. Chloride Channel Activators

6.1 Mectins (e.g., abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin)

7. Juvenile hormone mimetics

(eg, Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) 8. ecdysonagonists / disruptors

8.1 diacylhydrazines (e.g., chromafenozides, halofenozides, methoxyfenozides,

tebufenozide)

9. Inhibitors of chitin biosynthesis

9.1 Benzoylureas (e.g., bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron)

9.2 Buprofezin 9.3 Cyromazine

10. Inhibitors of oxidative phosphorylation, ATP disruptors

10.1 Diafenthiuron

10.2 Organotins (e.g., azocyclotin, cyhexatin, fenbutatin oxides) 5

11. Decoupling of the oxidative phosphorylation by interruption of the H proton gradient

11.1 Pyrroles (e.g., chlorfenapyr)

11.2 Dinitrophenols (e.g., binapacyrl, dinobutone, dinocap, DNOC) 0

12. Site I electron transport inhibitors

12.1 METI's (e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)

12.2 Hydramethylnone 5 12.3 Dicofol

13. Site II Electron Transport Inhibitors 13.1 Rotenone

o 14. Site III Electron Transport Inhibitors 14.1 Acequinocyl, Fluacrypyrim 15. Microwave Disruptors of Insect Dermal Membrane Bacillus thuringiensis strains

16. Inhibitors of fat synthesis

5 16.1 Tetronic acids (e.g., spirodiclofen, spiromesifen)

16.2 tetramic acids [e.g. 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-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 ( 2,5-dimethylphenyl) - o 8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)]

17. Carboxamides (e.g., flonicamid) 5

18. Octopaminergic agonists (e.g., Amitraz)

19. Inhibitors of Magnesium Stimulated ATPase O (e.g., Propargites)

20. phthalamides

(eg N ² - [1 _> 1-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N ¹ - [2-methyl-4- [1,2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-5 Reg.-No .: 272451-65-7), flubendiamide)

21. Nereistoxin Analogs

(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)

o 22. Biologics, hormones or pheromones

(eg, azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.) 23. Active substances with unknown or non-specific mechanisms of action

23.1 fumigants (e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides)

23.2 Selective feeding inhibitors (e.g., cryolites, flonicamid, pymetrozines) 23.3 mite growth inhibitors (e.g., clofentezines, etoxazoles, hexythiazox)

23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinomethionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flotenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, potassium oleate, pyrafluprole, pyralidyl, pyriprole, sulfluramide, tetradifon, tetrasul, triarathene, verbutin, and also the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) - 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) No. 185984-60-5) (see WO 96/37494, WO 98/25923), as well as preparations containing insecticidal plant extracts, nematodes, fungi or viruses.

A mixture with other known active ingredients, such as herbicides, safeners or semiochemicals or with fertilizers and growth regulators is possible.

The compounds (I), (II) and (III) can be applied simultaneously, either jointly or separately, or in succession, the sequence in the case of separate application generally having no effect on the control result.

The active ingredient combinations can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules become. The application is done in a conventional manner, for example by pouring, spraying, spraying, scattering, spreading, dry pickling, wet pickling, wet pickling, slurry pickling or encrusting.

When using the active compound combinations according to the invention, the application rates can be varied within a substantial range, depending on the mode of administration. In the treatment of parts of plants, the application rates of active ingredient combination are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the application rates of active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient combination are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The good fungicidal action of the active compound combinations according to the invention is evident from the examples below. While the individual active substances have weaknesses in the fungicidal action, the combinations show an effect that goes beyond a simple action summation.

A synergistic effect is always present in fungicides when the fungicidal action of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.

The expected effect for a given combination of 2 or 3 drugs can be found in S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicidal Combinations", Weeds 1967, 15, 20-22) are calculated as follows:

If X the efficiency when using the active ingredient A in one

Application rate of m ppm means

Y means the efficiency when using the active ingredient B in an application rate of n ppm,

_{iT iT} _II

Z the efficiency when using the active ingredient C in one

Application rate of LPP ^ means

E- _j the efficiency when using the active substances A and B in

Application rates of m and n ppm means and

Ε-i the efficiency when using the active substances A and B and C in

Application rates of m and n and r ppm means

then

X - Y

= X T Y -

100

and for a combination of 3 agents:

X X Y Y -X Z ^ Z X Y-Z

- 2 = X - v Y + Z -

100 10,000

The efficiency is determined in%. It means 0% an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

If the actual fungicidal effect is greater than calculated, then that is

Combination overdositive in its effect, i. it is a synergistic

Effect. In this case, the actual observed efficiency must be greater than the calculated value for the above formula the expected efficiencies Ei and E2.

The invention is illustrated by the following examples. However, the invention is not limited to the examples.

example

Pyricularia oryzae test (in vitro) / microtiter plates

The microtest is performed in microtiter plates with Potato Dextrose Broth (PDB) as a liquid test medium. The application of the active substances takes place as technical a.L, dissolved in acetone. For inoculation is a

Spore suspension of Pyricularia oryzae used. After 3 days

Incubation in the dark and with shaking (10 Hrz) becomes the

Light transmission in each filled well of the microtiter plates determined by means of a spectrophotometer.

Here, 0% means an efficiency equivalent to the growth in the controls, while an efficiency of 100% means that no fungal growth is observed.

It is clear from the table below that the effect found of the active ingredient combination according to the invention is greater than that calculated, ie that a synergistic effect is present.

TABLE

Pyricularia orvzae test (in vitro) / Microtest

Mixture according to the invention:

Mixture Effective- actual expectation value, ratio of effect calculated with active ingredient in degree Colby formula

(I) + (II) + (Ml) 1: 1: 1 1 + 1 + 1 87 56

Claims

claims

1. Active ingredient combination containing a compound of the formula

(Fluoxastrobin)

and

(1) a compound of the formula

ole)

and

(2) a compound of the formula

l)

2. Active ingredient combination according to claim 1, characterized in that in the active ingredient combination, the weight ratio of active ingredient of the formula (I) to

Active ingredient of the formula (II) is 1: 0.1 to 1: 100, and to

Active ingredient of the formula (III) is 1: 0.1 to 1: 30.

3. A method for controlling phytopathogenic fungi, characterized in that one acts a combination of active ingredients as defined in claim 1 or 2 on the fungi and / or their habitat or to keep them free from plants, plant parts, seeds, soils, surfaces, materials or spaces leaves.

4. The 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 1 simultaneously together or separately or successively.

5. Propagating material coated with an active ingredient combination according to one or more of claims 1 to 4.

6. A fungicidal composition containing a content of a drug combination as defined in claim 1.

7. Use of the active ingredient combination or agent as defined in claims 1, 2 and 6 defniert for controlling fungi.

8. A process for the preparation of fungicidal agents, characterized in that one mixes an active ingredient combination according to claim 1 with extenders and / or surface-active substances.

9. Use of active compound combinations according to claim 1 for the treatment of transgenic plants.

10. Use of active compound combinations according to claim 1 for the treatment of seed transgenic plants.