WO2007134777A2

WO2007134777A2 - Fungicidal active ingredient combinations

Info

Publication number: WO2007134777A2
Application number: PCT/EP2007/004374
Authority: WO
Inventors: Friedrich Kerz-Moehlendick; Stefan Herrmann; Olaf Gebauer; Peter Dahmen; Ulrike Wachendorff-Neumann
Original assignee: Bayer Cropscience Ag
Priority date: 2006-05-24
Filing date: 2007-05-16
Publication date: 2007-11-29
Also published as: AR061073A1; WO2007134777A3

Abstract

There are described novel synergistic active ingredient combinations which comprise firstly a known triazolopyrimidine derivative and secondly a known triazole derivative as well as at least one further fungicide and which are highly suitable for controlling phytopathogenic fungi.

Description

Fungicidal drug combinations

The present invention relates to novel drug combinations comprising a known triazolopyrimidine derivative, a known triazole derivative and at least one further fungicide selected from the list consisting of a known pyridinecarboxamide derivative, a morpholine derivative, a benzophenone derivative, an azole derivative and a benzacetamide derivative, and are very suitable for controlling phytopathogenic fungi.

It is already known that the triazolopyrimidine derivative 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5- a] pyrimidine has fungi-zide properties (see WO 98/46607). The effectiveness of this substance is good, but leaves at low application rates in some cases to be desired. The preparation of this compound is also known from WO 98/46607.

Furthermore, it is known that the triazole derivative l - [[3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiranyl] methyl] -1H, 2,4-triazole has fungicidal properties (cf. EP-A-196038). 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-196038.

It is also known that the pyridinecarboxamide derivative 2-chloro-N- (4'-chloro [1,1'-biphenyl] -2-yl) -3-pyridinecarboxamide has fungicidal properties (cf DE-195 31 813 or US Pat EP-A-545 099). 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 also known from DE 195 31 813 or EP-A-545 099.

Furthermore, it is known that the morpholine derivative is (+ -) - cis-4- [3- [4- (1,1-dimethylethyl) phenyl] -2-methylpropyl] -2,6-dimethylmorpholine (Reference: DE-A -265 67 47), the benzophenone derivative (3-bromo-6-methoxy-2-methylphenyl) (2,3,4-trimethoxy-6-methylphenyl) -methanone (Reference: EP-A-897 904) Azole derivative 5 - [(4-chlorophenyl) methyl] -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (Reference: EP-A-329 397) and the Benzacetamide derivative (E) -2 - [(2,5-dimethylphenoxy) methyl] -alpha (methoxyimino) -N-methylbenzacetamide ((Reference: EP-A-398 692) The effectiveness of these substances is good, but in some cases it leaves a lot to be desired at low application rates and the production of these compounds is also known.

Furthermore, fungicidal mixtures of two of the triazolopyrimidine derivative 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5- a] pyrimidine each with epoxiconazole (WO 2005/018328), boscalid (WO 04/045282), fenpropimorph (WO 2005/004608), Metrafenone (WO 04/045288), Metconazole (WO 2005/032249) and dimoxystrobin (WO 04/103075). The effectiveness of these blends is good, but at low levels it sometimes leaves much to be desired.

Likewise, two-fungicidal mixtures of the azole derivative epoxiconazole with other active compounds are known (see, for example, Fr. Phytoma (1993), 449, pages 54-7, WO 97/00012, EP-A 645 091). The effectiveness of these blends is good, but at low levels it sometimes leaves much to be desired.

Furthermore, ternary fungicide mixtures are known which contain the triazolopyrimidine derivative 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [1,1,5 -a] py-rimidine and a strobilurin derivative selected from pyraclostrobin and orysastrobin as a second mixture component and a third fungicide known (WO 2005/094583). The effectiveness of these blends is good, but at low levels it sometimes leaves much to be desired.

It has now been found that the new active ingredient combination, the 5-chloro-7- (4-methylpiperidin-l-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5 -a] pyrimidine of the formula (I)

and

(1) 1 - [[3- (2-Chloro-phenyl) -2- (4-fluoro-phenyl) -oxiranyl] -methyl] -LH-1, 2,4-triazole (Reference: EP-A-196038) of the formula (II)

iconazol)

and

(2) 2-Chloro-N- (4'-chloro [l, r-biphenyl] -2-yl) -3-pyridinecarboxamide (Reference: DE-19531813) of the formula (III)

lid

and or

(3) (+ -) - Cis-4- [3- [4- (1,1-dimethylethyl) phenyl] -2-methylpropyl] -2,6-dimethylmoholine (Reference: DE-A-265 6747) Formula (IV)

ropimorph

and or

(4) (3-bromo-6-methoxy-2-methylphenyl) (2,3,4-trimethoxy-6-methylphenyl> methanone (Reference: EP-A-897 904) of the formula (V)

fenone

and or (5) 5 - [(4-chlorophenyl) methyl] -2,2-dimethyl-1 - (1H-1,2,4-triazol-1-yl-methyl) cyclopentanol (reference: EP- A-329 397) of the formula (VI)

onazole

and or

(6) (E) -2 - [(2,5-Dimethylphenoxy) methyl] -alpha (methoxyimino) -N-methylbenzacetamide (Reference: EP-A-398 692) of the formula (VII)

strobin

contains very good fungicidal properties.

Surprisingly, the fungicidal action of the active ingredient combination according to the invention is substantially 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.

With regard to effective resistance management and effective control of pathogen-associated harmful fungi with the lowest possible application rates, the present invention was based on mixtures which show an improved action against harmful fungi with a reduced total amount of active substances applied (synergistic mixtures).

It has also been found that with simultaneous joint or separate application of the compounds of formula (I) and (II) and at least one other of the compounds (III), (IV), (V), (VI) and (VII) or when the compound of the formula (I) and (II) and at least one other of the compounds (III), (IV), (V), (VI) and (VII) are used, it is possible to combat harmful fungi better than the individual compounds or with the binary mixtures described earlier. The active ingredient of formula (I) is known (see WO-A-98 46607). The active compounds of the formulas (II), (III), (IV), (V), (VI) and (VII) are likewise known (see the references given).

From the structural formula for the active ingredient of the formula (VII) it can be seen that the compound can be present as an E or Z isomer. The compound (VII) 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 (VII) in which the compound of the formula (VII) is present as an E isomer.

It can be seen from the structural formulas for the active compounds of the formulas (II), (IV) and (VI) that the compounds can each be present as (-) - or as (+) - enantiomer. The compounds of the formulas (II), (IV) and (VI) can therefore be present as a racemate or else in the form of a single enantiomer. Preference is given to the compounds of the formulas (II), (IV) and (VI) in which the racemate is in each case present.

By the (-) - enantiomer is meant here in each case the enantiomer which rotates the oscillation plane of linearly polarized light of the sodium D line to the left.

The active ingredient combination according to the invention contains the active compounds of the formulas (I) and (II) and at least one further active ingredient selected from those of the formulas (III), (IV), (V), (VI) and (VII). It can also contain other fungicidal Zumischkomponenten beyond.

Emphasis is given to active compound combinations according to the invention which, in addition to the triazolopyrimidine derivative (I), 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine and the azole derivative of the formula (II) contain a further mixing partner selected from the substances of the formulas (III) to (VII).

In particular, the following active substance combinations are preferred:

5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, epoxiconazole and boscalid

5-Chloro-7- (4-methylpiperidin-1-yl)) - 6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, epoxiconazole and fenpropimorph

5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, epoxiconazole and metrafenone

5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, epoxiconazole and metconazole 5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, epoxiconazole and dimoxystrobin

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 10 parts by weight, preferably 0.2 to 5 parts by weight of active compound of the formula (II),

and

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (III)

and or

0.2 to 20 parts by weight, preferably 0.5 to 10 parts by weight of active compound of the formula (IV)

and or

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (V)

and or

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (VI)

and or

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (VII)

The mixing ratio is preferably to be chosen so that a synergistic mixture is obtained.

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. The active compound combinations according to the invention are particularly suitable for controlling Mycosphaerella graminicola (= Septoria tritici), Puccinia recondita, Erysiphe graminis and Phakopsora pachyrhizi.

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, 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 causative agents of rust diseases, such as Gymnosporangium species, such as, for example, Gymnosporangium sabinae Hernileia species, such as, for example, 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, 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, for example, 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 Mycosphaerella 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 rots and wilts, as well as 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;

Helminthosporium species, such as Helminthosporium solani;

Diseases caused by bacterial pathogens such as Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as 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 Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megaspa- ma), Brown Star Red (Phialophora gregata), Pythium red (Pythium aphanidermatum, Pythium irregular , Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Star Decay (Sclerotinia sclerotium rum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).

The compounds of the formula (I) and (II) and at least one further compound of the formula (III), (IV), (V), (VI) and (VII) can be applied simultaneously together or separately or sequentially, the sequence with separate application in general has no effect on the control success.

The compositions according to the invention are suitable for the protection of all crops cultivated in agriculture, 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 tomato, cucumber, onions and lettuce), 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 active compound combinations according to the 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-enhancing (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 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.

The good plant tolerance of the active substance combinations in the concentrations necessary for combating plant diseases makes it possible to treat whole plants (above-ground parts of plants and roots), planting and seed, and the soil. The active compound combinations according to the invention can be used for foliar application or as a mordant.

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 particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire 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 are not always solved satisfactorily. you can. 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 above-ground parts of plants 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 condition that 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 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 breeders' 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 substance combinations takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, pouring, spraying, evaporating, Nebulizing, spreading, spreading and propagating material, especially in seeds, further by single or multi-layer wrapping.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild species or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant varieties and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, 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 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.

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 bottoms, 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 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 viruses as well as an increased tolerance of the plants against certain hereditary bizide agents. 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), CryΙA (b ), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter "Bt 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 (eg "PAT" gene). The genes which confer the desired properties ("traits") may 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® (US Pat. eg corn, cotton, soy), 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), IMI® (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 plant varieties developed or to be marketed in the future with these or future developed genetic traits.

The process for controlling harmful fungi is carried out by the separate or combined application of the compounds of the formula (I) and (II) and at least one further active compound selected from the compounds of the formula (III), (IV), (V), (VI) and (VII) or the mixtures of the compounds of the formula (I), (II) and at least one further active compound selected from the compounds of the formula (III), (IV), (V), (VI) and (VII) Spraying, spraying or dusting the seeds, plants or soils before or after sowing the plants or before or after emergence of the plants.

Depending on their respective physical and / or chemical properties, the active compound combinations according to the invention can be converted into the customary formulations, 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 very fine encapsulation in polymeric materials 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 substances or the active substance 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-forming 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 those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as butane, propane, nitrogen and carbon dioxide.

Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates. Suitable solid carriers for granules are: e.g. Cracked 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 emulsifying and / or foaming agents are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: e.g. Lignin-Sulfϊtablaugen and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers, such as gum arabic, can be used in the formulations. 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 ingredient concentration of the use forms 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 undesired phytopathogenic fungi 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, 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 (drenching), drip irrigation, spraying, spraying, scattering, dusting, foaming, brushing, spreading, dry pickling, moist pickling, wet pickling, slurry pickling, encrusting, etc.

The active compound combinations according to the invention can be present in commercial formulations and in the formulations prepared from these formulations in admixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances 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 ingredient 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 compound 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 summation of effect.

A synergistic effect is always present in fungicides if the fungicidal action of the active substance combinations is greater than the sum of the effects of the individually applied active substances.

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 means the efficiency when using the active substance A in an application rate of m g / ha,

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

Z means the efficiency when using the active ingredient C in an application rate of r g / ha,

El means the efficiency when using the active compounds A and B in application rates of m and n g / ha means and

E2 means the efficiency when using the active compounds A and B and C in application rates of m and n and rg / ha, then

¹ 100

and for a combination of 3 agents:

(X ^• Y + X ^• Z + Y ^• Z) XYZ

E2 = X + 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.

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

example 1

Pyrenophora teres test (barley) / protective

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 ingredient or combination of active ingredients with the specified amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration or diluted a commercial formulation of active ingredient or combination of active ingredients 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 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 Ia

Pyrenophora teres test (barley) / protective

gef. = found effect

** calc. = calculated according to the Colby formula

Table Ib

Pyrenophora teres test (barley) / protective

gef. = found effect

* ♦ calc. = Calculated according to the Colby formula Example 2

Pyrenophora teres test (barley) / curative

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

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Pyrenophora teres sprayed. The plants remain 48 hours at 2O ⁰ C and 100% relative humidity in an incubation cabin. Subsequently, the plants with the

Dried active ingredient preparation in the specified rate.

The plants are placed in a greenhouse at a temperature of about 20 ⁰ C and relative humidity of about 80%.

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.

Table 2a

Pyrenophora teres test (barley) / curative

gef. = found effect

♦ * calc. = Calculated according to the Colby formula

Table 2b

Pyrenophora teres test (barley) / curative

gef. = found effect

** calc. = calculated according to the Colby formula

Claims

claims

1. Synergistic fungicidal drug combinations containing a compound of the formula (D

and

(1) a compound of the formula (II)

oxiconazole)

and

(2) a compound of the formula (III)

alid

and or

(3) a compound of the formula (IV)

imorph

and or

(4) a compound of the formula (V)

rafenone

and or

(5) a compound of the formula (VI)

onazole

and or

(6) a compound of the formula (VII)

strobin

2. active compound combinations according to claim 1, characterized in that in the

Active ingredient combination the weight ratio of active ingredient of the formula (I)

Active ingredient of the formula (II) is 1: 0.1 to 1: 10, and to

Active ingredient of the formula (III) is 1: 0.1 to 1: 10, and / or to

Active ingredient of the formula (IV) is 1: 0.2 to 1: 20, and / or to

Active ingredient of the formula (V) is 1: 0.1 to 1: 10, and / or to

Active ingredient of the formula (VI) is 1: 0, 1 to 1: 10, and / or to

Active ingredient of the formula (VII) 1: 0.1 to 1: 10.

3. A method for controlling unwanted phytopathogenic fungi, characterized in that one defines a combination of active ingredients as defined in claim 1 on the fungi and / or their habitat and / or the plants to be kept by them, plant parts, seeds, soils, surfaces, materials or spaces allow to act.

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 and / or the compound (IV) according to claim 1 and / or the compound (V) according to claim 1 and / or the compound (VI) and / or the compound (VII) according to claim 1 simultaneously together or separately or successively bring.

5. Propagating material which has been treated by a method according to claim 3.

6. A fungicidal composition containing a content of an active ingredient combination according to one or more of claims 1 to 2.

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

8. Use of the active ingredient combination or agent as defined in claims 1, 2 and 6 for the treatment of seed.

9. Use of the active ingredient combination or agent as defined in claims 1, 2 and 6 for the treatment of transgenic plants.

10. Use of the active ingredient combination or agent as defined in claims 1, 2 and 6 for the treatment of seed transgenic plants.

1 1. A process for the preparation of fungicidal agents, characterized in that one mixes active compound combination according to one or more of claims 1 to 2 with stretch mittein and / or surface-active substances.