WO2008061654A1

WO2008061654A1 - Fungicidal active agent combination

Info

Publication number: WO2008061654A1
Application number: PCT/EP2007/009824
Authority: WO
Inventors: Peter Dahmen; Stefan Dutzmann; Friedrich Kerz-Moehlendick; Isolde HÄUSER-HAHN; Karin Wieczorek
Original assignee: Bayer Cropscience Ag
Priority date: 2006-11-24
Filing date: 2007-11-14
Publication date: 2008-05-29
Also published as: AR063900A1; BRPI0719337A2; EP2094088A1

Abstract

The novel active agent combinations comprising tebuconazole and epoxiconazole have excellent fungicidal properties.

Description

Fungicidal drug combinations

The present invention relates to novel drug combinations containing the known fungicidal active ingredients tebuconazole and epoxiconazole, which are very well suited for controlling unwanted phytopathogenic fungi.

It is already known that tebuconazoles and epoxiconazoles have fungicidal properties (see Pesticide Manual, Edition (1997), pages 79, 466 and 1144, EP-A 0 040 345, EP-A 0 196 038). The effectiveness of these substances is good, but leaves at low application rates in some cases to be desired.

It has now been found that active substance combinations comprising tebuconazole [(RS) -I-p-chlorophenyl-4,4-dimethyl-3- (1H-l, 2,4-triazol-1-ylmethyl) -pentan-3-ol, Reference: EP-A 0 040 345] of the formula (I)

and

Epoxiconazole {(2RS, 3SR) -1 - [3- (2-chloro-phenyl) -2,3-epoxy-2- (4-fluorophenyl) -propyl] -LH-1, 2,4-triazole, Reference: EP-A 0 196038} of the formula (II)

possess very good fungicidal properties.

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 substances in the active substance combinations can be varied within a relatively wide range.

In general, 1 part by weight of active ingredient of the formula (I)

0.05 to 10 parts by weight, preferably 0.1 to 2 parts by weight, more preferably 0.2 to 1 part by weight of active compound of the formula (H). Very particular preference is given to 1 part by weight of active compound of the formula (I) 0.5 to 1 part by weight of active compound of the formula (H). Emphasized are the mixing ratios of active ingredient of the formula (I) to active ingredient of the formula QI) of 2: 1, 3: 2 and 1: 1 (see also the examples).

In any case, the mixing ratio should be such that a synergistic mixture is obtained.

The Wirkstofϊkombination invention, applied simultaneously, together or separately, has a strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

By way of example, but not by way of limitation, some pathogens of fungal diseases, which fall under the abovementioned generic terms, are named:

Diseases caused by powdery mildews such as e.g. Blumeria species, e.g. Blumeria graminis; Podosphaera species, e.g. Podosphaera leucotricha; Sphaerotheca species, e.g. Sphaerotheca fuliginea; Uncinula species, e.g. 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 or Puccinia triticina; Uromyces species, such as Uromyces appendiculatus; Diseases caused by pathogens of the group of Oomycetes such as 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, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species such as Pythium ultimum; Leaf spot diseases and leaf wilt caused by eg 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 fawcettü; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as eg Leptosphaeria raaculans; Magnaporthe species, such as Magnaporthe grisea; Mycosphaerella species, such as Mycosphaerella graminicola; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophila species, such as 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 incamata; Venturia species, such as Venturia inaequalis;

Root and stem diseases caused by e.g. Corticium species, e.g. Corticium graminearum; Fusarium species, e.g. Fusarium oxysporum; Gaeumannomyces species, e.g. Gaeuman- nomyces graminis; Rhizoctonia species, e.g. Rhizoctonia solani; Tapesia species, e.g. Tapesia acuformis; Thielaviopsis species, e.g. Thielaviopsis basicola; Ear and panicle diseases (including corncob) caused by e.g. Alternaria species, e.g. Alternaria spp .; Aspergillus species, e.g. Aspergillus flavus; Cladosporium species, e.g.

Cladosporium spp .; Claviceps species, e.g. Claviceps purpurea; Fusarium species, e.g. Fusarium culmorum; Gibberella species, e.g. Gibberella zeae; Monographella species, e.g. Monographella nivalis; Diseases caused by fire fungi, e.g. Sphacelotheca species, e.g. Sphacelotheca reiliana; Tilletia species, e.g. Tilletia caries; Urocystis species, e.g. Urocystis occulta; Ustilago

Species, e.g. Ustilago nuda;

Fruit rot caused by e.g. Aspergillus species, e.g. Aspergillus flavus; Botrytis species, e.g. Botrytis cinerea; Penicillium species, e.g. Penicillium expansum; Sclerotinia species, e.g. Sclerotinia sclerotiorum; Verticilium species, such as e.g. Verticilium alboatrum;

Seed and soil rots and wilts, as well as seedling diseases caused by e.g.

Fusarium species, e.g. Fusarium culmorum; Phytophthora species, e.g. Phytophthora cactorum;

Pythium species, e.g. Pythium ultimum; Rhizoctonia species, e.g. Rhizoctonia solani; sclerotium

Species, e.g. Sclerotium rolfsii; Cancers, galls and witches brooms caused by e.g. Nectria species, e.g. Nectria galligena;

Weikeerkrankungen caused by e.g. Monilinia species, e.g. Monilinia laxa;

Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, e.g.

Taphrina deformans; Degenerative diseases of woody plants caused by e.g. Esca species, e.g. Phemmoniella clamydospora;

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

Diseases of plant tubers caused by eg Rhizoctonia species, such as Rhizoctonia solani; - A -

Diseases caused by bacterial agents such as e.g. Xanthomonas species, e.g. Xanthomonas campestris pv. Oryzae; Pseudomonas species, e.g. Pseudomonas syringae pv. Lachrymans; Erwinia species, e.g. Erwinia amylovora;

Preferably, the following diseases of soybean beans can be controlled:

Fungal diseases on leaves, stems, pods and seeds caused by e.g.

Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)) , Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Powdery Mildew (Phyllosticta sojaecola) Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola )

Fungal diseases on roots and stem base caused by e.g.

Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular , Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola) ,

The compositions according to the invention are suitable for the protection of all crops cultivated in the agricultural sector, in the greenhouse, in forests or in horticulture. In particular, these are cereal crops (such as wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugar beet and fodder), peanut, vegetables (such as eg tomato, cucumber, onions and salad), wine, fruit (such as apple, banana, pear and cherry), lawn and ornamental plants. In the treatment of seeds, cereals (such as wheat, barley, rye and oats), corn and rice are of particular importance. The Wirkstofϊkombinationen invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.

In the present context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.

Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens. The period within which protection is provided generally extends from 1 to 28 days, preferably 1 to 14 days after the treatment of the plants with the active ingredients or up to 200 days after a seed treatment.

In addition, can be reduced by the treatment according to the invention, the mycotoxin content in the crop and the food and feed produced therefrom. Deoxynivalenol (DON), Nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, Fumonisins, Zearalenone, Moniliformin, Fusarin, Diaceotoxyscirpenol (DON), especially, but not exclusively, are mentioned here. DAS), beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, parulin, ergot alkaloids and aflatoxins, which can be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acuminatum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitecrum, F. solani, F. sporotrichoid, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, and others as well as of Aspergillus spec, Penicillium spec, Claviceps purpurea, Stachybotrys spec and others.

The good plant tolerance of the active substance combinations in the concentrations necessary for controlling plant diseases allows treatment of whole plants (above-ground parts of plants and roots), of planting and seed, and of the soil. The active compound combinations according to the invention can be used for foliar application or else as seed dressing.

Much of the damage to crop plants caused by phytopathogenic fungi is already produced by infestation of the seed during storage and after introduction of the seed into the soil and during and immediately after germination of the plants. This phase is especially critical, because the roots and shoots of the growing plant are particularly sensitive and already a small damage can lead to the death of the whole plant. There is therefore a particular interest in protecting the seed and the germinating plant by the use of suitable agents.

The control of phytopathogenic fungi by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant, which eliminate or at least significantly reduce the additional application of crop protection agents after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant is best protected against attack by phytopathogenic fungi, but without damaging the plant itself by the active ingredient used. In particular, methods for treating seed should also include the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of pesticide use.

The present invention therefore more particularly relates to a method of protecting seeds and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention.

The control of phytopathogenic fungi, which damage plants after emergence, takes place primarily through the treatment of the soil and the aerial plant parts with plant protection agents. Due to concerns about the potential impact of crop protection products on the environment and human and animal health, efforts are being made to reduce the amount of active ingredients applied.

One of the advantages of the present invention is that because of the particular systemic properties of the compositions of the invention, treatment of the seed with these agents not only protects the seed itself, but also the resulting plants after emergence from phytopathogenic fungi. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.

It is likewise to be regarded as advantageous that the mixtures according to the invention can also be used in particular in the case of transgenic seed. In the context of the present invention, the agent according to the invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight. Alternatively, seed can also be used, which after drying, for example, treated with water and then dried again.

In general, care must be taken in the treatment of the seed that the amount of the agent and / or other additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.

The agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.

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.

If appropriate, the active compound combinations according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.

According to the invention, all plants and parts of plants can be treated. In this context, plants are to be understood as meaning all plants and plant populations, such as desired and unwanted plants or crop plants (including naturally occurring crop plants). Crop plants can be plants produced by conventional breeding and optimization methods or can be obtained 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 rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

The treatment according to the invention of the plants and plant parts with the active compound combinations takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, vaporizing, atomizing, spreading, spreading, pouring and in propagation material, in particular in seeds, further by single or multi-layer wrapping.

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

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.

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 give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products possible, which go beyond the actual expected effects.

The preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification 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 water or soil salinity, 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 Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or vire n 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 CryΙA (a), CryIA (b), CryIA (c), CryHA, CryHIA, CryDIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter, 3t plants "). Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example, imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example, JPAT "gene). The genes conferring the desired properties ("traits") can also be present in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), 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 to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to the future developed or future on the market coming plant varieties with these or future developed genetic traits ("Traits").

The method for controlling harmful fungi is carried out by the separate or combined application of the compounds of formula (I) and (fl) or the mixtures of the compounds of formula (I) and (II) by spraying or dusting the seeds, the plants or Soils before or after sowing the plants or before or after emergence of the plants.

The active compound combinations according to the invention can be converted into the customary formulations depending on their respective physical and / or chemical properties, such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, Active substance-impregnated natural and synthetic substances as well as ultra-fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV-KaIt and warm mist formulations.

These formulations are prepared in a known manner, e.g. 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 foam-producing agents.

In the case of using water as an extender, e.g. also organic solvents can 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, e.g. Petroleum fractions, mineral and vegetable oils, 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, ammonium salts and 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 a solid carrier Materials for granules are suitable: eg 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 stems. Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.

It can be used in the formulations adhesives such as carboxymethyl cellulose, natural and synthetic see powdery, granular or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and 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 active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active compound concentration of the forms of use for controlling animal pests such as insects and acarids may be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. The application is done in a custom forms adapted to the application forms.

The formulations for controlling unwanted phytopathogenic fungi generally contain between 0.1 and 95% by weight of active substances, preferably between 0.5 and 90%.

The active compound combinations according to the invention 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, dusts and granules. The application is done in the usual way, e.g. by pouring (drenchen), drip irrigation, splashing, spraying, scattering, dusting, foaming, brushing, spreading, dry pickling, wet pickling, wet pickling, slurry pickling, encrusting, etc.

The active compound combinations according to the invention can be used in commercial formulations as well as in the formulations prepared from these formulations in admixture with others Active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.

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 compound combination are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the seed treatment, the application rates of active ingredient 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 active ingredient combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, and further processing aids.

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 drugs can be found in S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicidal Combinations", Weeds 1967, j_5, 20-22) are calculated as follows:

If

X means the efficiency when using the active ingredient A at a rate of mg / ha, - -

Y means the efficiency when using the active ingredient B in an application rate of n g / ha and E means the efficiency when using the active compounds A and B in application rates of m and n g / ha,

XxY then E = X + Y--

100

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, the combination is over-additive in its effect, i. there is a synergistic effect. In this case, the actual observed efficiency must be greater than the expected efficiency value (E) calculated from the above formula.

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

Application Examples Example A

Erysiphe test (barley) / curative

Solvent: 50 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or combination of active ingredients with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for curative efficacy, young plants with spores of Erysiphe graminis f.sp. hordei pollinated. 48 hours after inoculation, the plants are sprayed with the preparation of active compound in the stated application rate. The plants are grown in a greenhouse at a temperature of about 20 ⁰ C and a relative

Humidity of about 80% set up to favor the development of powdery mildew pustules.

6 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no

Infestation is observed. Example Bl

Pyrenophora teres test (barley) / curative

Solvent: 50 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound or combination of active ingredients with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for curative activity, young plants are sprayed with a conidia suspension of Pyrenophora (Eres.) The plants remain in an incubation cabin for 48 hours at 20 ^° C. and 100% relative humidity, after which the plants are sprayed with the preparation of active compound at the stated application rate.

The plants are placed in a greenhouse at a temperature of about 2O ⁰ C and a relative humidity of about 80%. 12 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Example B2

Pyrenophora teres test (barley) / protective Solvent: 50 parts by weight N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or combination of active ingredients with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain 48 hours at 20 ⁰ C and 100% relative humidity in an incubation cabin. The plants are then placed in a greenhouse at a temperature of about 20 ⁰ C and a relative humidity of about 80%.

10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. - -

Table Bl: Pyrenophora teres test (barley) / protective

gef. = found effect

** calc. = calculated according to the Colby formula

Example C

Erysiphe test (barley) / protective Solvent: 50 parts by weight N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or combination of active ingredients with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate.

After the spray coating has dried, the plants are planted with spores of Erysiphe graminis f.sp. hordei pollinated. The plants are placed in a greenhouse at a temperature of about 2O ⁰ C and a relative humidity of about 80% to promote the development of mildew pustules. 6 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. Example D

Leptosphaeria nodorum test (wheat) / curative

Solvent: 50 parts by weight of N, N-dimethylacetamide

To test for curative efficacy, young plants with a conidia suspension of

Leptosphaeria nodorum sprayed. The plants remain 48 hours at 20 ⁰ C and 100% relative humidity in an incubation and are then sprayed with the active ingredient preparation in the specified rate.

The plants are grown in a greenhouse at a temperature of about 15 ° C and a relative

Humidity of about 80% set up.

8 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no

Infestation is observed.

Example E

Leptosphaeria nodorum test (wheat) / protective Solvent: 50 parts by weight N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or combination of active ingredients with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain 48 hours at 20 ⁰ C and 100% relative humidity in an incubation cabin. The plants are placed in a greenhouse at a temperature of about 15 ⁰ C and a relative humidity of about 80%.

11 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. Example F

Puccinia recondita test (wheat) / curative

Solvent: 50 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for curative efficacy, young plants with a condom suspension of

Puccinia recondita sprinkles. The plants remain for 48 hours at 20 ° C and 100% relative humidity in an incubation cabin. Subsequently, the plants are sprayed with the preparation of active compound in the stated application rate.

The plants are grown in a greenhouse at a temperature of about 20 ⁰ C and a relative

Humidity of about 80% set up to favor the development of rust pustules.

Infestation is observed.

Example G

Sphaerotheca fuliginea test (cucumber) / protective Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed at about 23 ° C and a relative humidity of about 70% in the greenhouse. 7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. Example H

Alternaria solani test (tomato) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabin at about 20 ⁰ C and 100% relative humidity. 3 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Example I

Phytophthora infestans test (tomato) / protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at about 20 ⁰ C and 100% relative humidity.

3 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Example J

Plasmopara viticola test (vine) / protective Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide ,

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test specimen for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain for 1 day in an incubation cabin at about 20 ⁰ C and 100% relative humidity. The plants are then placed in the greenhouse for 4 days at about 21 ⁰ C and about 90% humidity. The plants are then moistened and placed in an incubation booth for 1 day.

6 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Example K

Botrytis cinerea - test (bean) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at about 20 ⁰ C and 100% relative humidity. 2 days after the inoculation, the size of the infestation spots on the leaves is evaluated. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Example L

PyricuJaria 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 ingredients is carried out as a technical ai, dissolved in acetone. For inoculation, a spore suspension of Pyricularia oryzae is used. After 3 days incubation - In darkness and with shaking (10 Hz) the light transmission in each filled cavity of the microtiter plates is 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.

Example M

Rhizoctonia solani test (in vitro) / microtiter plates

The microtest is performed in microtiter plates with Potato Dextrose Broth (PDB) as a liquid

Stirred medium. The application of the active ingredients is carried out as a technical a.i., dissolved in acetone. For inoculation, a mycelial suspension of Rhizoctonia solani is used. After 5 days of incubation in the dark and with shaking (10 Hz), the light transmission in each filled well of the microtiter plates is 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.

Example N

Gibberella zeae 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 ingredients is carried out as a technical a.i., dissolved in acetone. For inoculation, a spore suspension of Gibberella zeae is used. After 3 days of incubation in the dark and with shaking (10 Hz), the light transmittance in each filled well of the microtiter plates is determined by means of a spectrophotometer.

Example O

Botrytis cinerea 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 ingredients is carried out as a technical ai, dissolved in acetone. For inoculation, a spore suspension of Botrytis cinerea is used. After 7 days of incubation in the dark and with shaking (10 Hz), the light transmittance in each filled well of the microtiter plates is 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. - -

Example P

Septoria tritici test (wheat) / protective

Solvent: 50 parts by weight of N, N-dimethylacetamide

Eraulgator: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound or active compound combination with the specified amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain 48 hours at 20 ⁰ C and 100% relative humidity in an incubation cabin.

The plants are placed in a greenhouse at a temperature of about 15 ⁰ C and a relative humidity of 80%.

21 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Table P: Septoria tritici test (wheat ^" ) / protective

Claims

claims

1. Fungicidal active substance combinations containing tebuconazoles of the formula (I)

and epoxiconazoles of the formula (H)

2. Fungicidal active ingredient combination according to claim 1, wherein the active compounds of the formulas (I) and (II) are used in a synergistically effective mixing ratio.

3. Fungicidal combination of active substances according to one of claims 1 or 2, characterized in that per 1 part by weight of active compound of the formula (I), 0.05 to 10, preferably 0.1 to 2, particularly preferably 0.2 to 1, parts by weight Active ingredient of the formula (D) omitted.

4. Fungicidal active ingredient combination according to one of claims 1, 2 or 3, characterized in that the mixing ratio of active ingredient of the formula (I) to active ingredient of the formula (E) from a ratio of 2: 1, 3: 2 and 1: 1 selected is.

5. Use of active compound combinations according to one of claims 1, 2, 3 or 4 for controlling unwanted phytopathogenic fungi.

6. Use of active compound combinations according to any one of claims 1, 2, 3 or 4 for the treatment of seed.

7. Use of active compound combinations according to any one of claims 1, 2, 3 or 4 for

Treatment of transgenic plants.

8. Use of active compound combinations according to one of claims 1, 2, 3 or 4 for

Treatment of seeds of transgenic plants.

9. seed which has been treated with an active ingredient combination according to any one of claims 1, 2, 3 or 4.

10. A method for controlling undesirable phytopathogenic fungi, characterized in that one applies active compound combinations according to any one of claims 1, 2, 3 or 4 to the undesirable phytopathogenic fungi and / or their habitat and / or seed.

11. A process for the production of fungicidal agents, characterized in that mixing active compound combinations according to any one of claims 1, 2 or 3 with extenders and / or surface-active substances.