DE102006022758A1 - Fungicidal drug combinations - Google Patents

Abstract

wobei die Reste R¹ und R² die in der Beschreibung angegebenen Bedeutungen haben,
B) Azoxystrobin (II), Fluidoxonil (III),
C) Triazon (IV), Triazoxide (V), Silthiofam (VI).
Die Wirkstoffkombinationen sind sehr gut zur Bekämpfung von unerwünschten phytopathogenen Pilzen geeignet. Insbesondere eignen sich die erfindungsgemäßen Wirkstoffkombinationen zur Behandlung von Saatgut.The present invention relates to novel drug combinations consisting of at least three fungicidal components A, B and C. A, B and C may be selected from the following compounds:
A) the compounds of general formula (I),

where the radicals R ¹ and R ^{2 have} the meanings given in the description,
B) Azoxystrobin (II), Fluidoxonil (III),
C) Triazone (IV), triazoxide (V), silthiofam (VI).
The drug combinations are very well suited for controlling unwanted phytopathogenic fungi. In particular, the active compound combinations according to the invention are suitable for the treatment of seed.

Description

The The present invention relates to novel drug combinations which consist of three known fungicidal agents. These new ones Mixtures are very good for controlling unwanted phytopathogenic fungi.

in der
R¹ für Trifluormethyl oder Difluormethyl steht und
R² für Wasserstoff oder Methyl stehen, fungizide Eigenschaften aufweisen.It is already known that compounds of the general formula (I)

in the
R ^{1 is} trifluoromethyl or difluoromethyl and
R ^{2 are} hydrogen or methyl, have fungicidal properties.

The Compounds of general formula (I) are known from e.g. WHERE 2006/015865 A1.

in the The following compounds of the formulas (I-1) - (I-4) may be mentioned individually.

welches aus EP 00 382 375 bekannt ist, fungizide Eigenschaften aufweist. Ferner ist bekannt, dass Fludioxonil der Formel (III),

welches EP 00 206 999 bekannt ist, fungizide Wirkungen hat.Furthermore, it is known that azoxystrobin of the formula (II),

which off EP 00 382 375 is known to have fungicidal properties. Furthermore, it is known that fludioxonil of the formula (III),

which EP 00 206 999 is known to have fungicidal effects.

in welcher
Q für Wasserstoff oder SH steht,
m für 0 oder 1 steht,
R¹³ für Wasserstoff, Fluor, Chlor, Phenyl oder 4-Chlor-phenoxy steht,
R¹⁴ für Wasserstoff oder Chlor steht,
A⁴ für eine direkte Bindung, -CH₂-, -(CH₂)₂-, -O-, für *-CH₂-CHR¹⁷- oder *-CH=CR¹⁷- steht, wobei die mit * markierte Bindung mit dem Phenylring verknüpft ist, und
R¹⁵ und R¹⁷ dann zusammen für -CH₂-CH₂-CH[CH(CH₃)₂]- oder -CH₂-CH₂-C(CH₃)₂- stehen,
A⁵ für C oder Si (Silizium) steht,
A⁴ außerdem für -N(R¹⁷)- steht und A⁵ außerdem zusammen mit R¹⁵ und R¹⁶ für die Gruppe C=N-R¹⁸ steht, wobei R¹⁷ und R¹⁸ dann zusammen für die Gruppe

stehen, wobei die mit * markierte Bindung mit R¹⁷ verbunden ist,
R¹⁵ für Wasserstoff, Hydroxy oder Cyano steht,
R¹⁶ für 1-Cyclopropylethyl, 1-Chlorcyclopropyl, C₁-C₄-Alkyl, C₁-C₆-Hydroxyalkyl, C₁-C₄-Alkylcarbonyl, C₁-C₂-Halogenalkoxy-C₁-C₂-alkyl, Trimethylsilyl-C₁-C₂-alkyl, Monofluorphenyl, oder Phenyl steht,
R¹⁵ und R¹⁶ außerdem zusammen für -O-CH₂-CH(R¹⁸)-O-, -O-CH₂-CH(R¹⁸)-CH₂-, oder -O-CH-(2-Chlorphenyl)- stehen,
R¹⁸ für Wasserstoff, C₁-C₄-Alkyl oder Brom steht, fungizid wirksam sind.Furthermore, it is known that Triazoles of the general formula (IV)

in which
Q is hydrogen or SH,
m is 0 or 1,
R ^{13 is} hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy,
R ^{14 is} hydrogen or chlorine,
A ^{4 is} a direct bond, -CH ₂ -, - (CH ₂ ) ₂ -, -O-, for * -CH ₂ -CHR ¹⁷ - or * -CH = CR ¹⁷ -, wherein the bond marked with * the phenyl ring is linked, and
R ¹⁵ and R ¹⁷ together then represent -CH ₂ -CH ₂ -CH [CH (CH ₃ ) ₂ ] - or -CH ₂ -CH ₂ -C (CH ₃ ) ₂ -,
A ^{5 is} C or Si (silicon),
A ⁴ also represents -N (R ¹⁷ ) - and A ⁵ together with R ¹⁵ and R ^{16 also represents} the group C = NR ¹⁸ , where R ¹⁷ and R ¹⁸ then together represent the group

with the bond marked with * attached to R ¹⁷ ,
R ^{15 is} hydrogen, hydroxy or cyano,
R ^{16 is} 1-cyclopropylethyl, 1-chlorocyclopropyl, C ₁ -C ₄ -alkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₂ -haloalkoxy-C ₁ -C ₂ -alkyl , Trimethylsilyl-C ₁ -C ₂ -alkyl, monofluorophenyl, or phenyl,
R ¹⁵ and R ¹⁶ also together represent -O-CH ₂ -CH (R ¹⁸ ) -O-, -O-CH ₂ -CH (R ¹⁸ ) -CH ₂ -, or -O-CH- (2-chlorophenyl) - stand,
R ^{18 is} hydrogen, C ₁ -C ₄ alkyl or bromine, are fungicidally active.

Etaconazole (bekannt aus DE-A 25 51 560) der Formel (IV-2),

Propiconazole (bekannt aus DE-A 25 51 560) der Formel (IV-3),

Difenoconazole (bekannt aus EP-A 0 112 284) der Formel (IV-4),

Bromuconazole (bekannt aus EP-A 0 258 161) der Formel (IV-5),

Cyproconazole (bekannt aus DE-A 34 06 993) der Formel (IV-6),

Hexaconazole (bekannt aus DE-A 30 42 303) der Formel (IV-7),

Penconazole (bekannt aus DE-A 27 35 872) der Formel (IV-8),

Myclobutanil (bekannt aus EP-A 0 145 294) der Formel (IV-9),

Tetraconazole (bekannt aus EP-A 0 234 242) der Formel (IV-10),

Flutriafol (bekannt aus EP-A 0 015 756) der Formel (IV-11),

Epoxiconazole (bekannt aus EP-A 0 196 038) der Formel (IV-12),

Flusilazole (bekannt aus EP-A 0 068 813) der Formel (IV-13),

Simeconazole (bekannt aus EP-A 0 537 957) der Formel (IV-14),

Prothioconazole (bekannt aus WO 96/16048) der Formel (IV-15),

Fenbuconazole (bekannt aus DE-A 37 21 786) der Formel (IV-16),

Tebuconazole (bekannt aus EP-A 0 040 345) der Formel (IV-17),

Ipconazole (bekannt aus EP-A 0 329 397) der Formel (IV-18),

Metconazole (bekannt aus EP-A 0 329 397) der Formel (IV-19),

Triticonazole (bekannt aus EP-A 0 378 953) der Formel (IV-20),

Bitertanol (bekannt aus DE-A 23 24 010) der Formel (IV-21),

Triadimenol (bekannt aus DE-A 23 24 010) der Formel (IV-22),

Triadimefon (bekannt aus DE-A 22 01 063) der Formel (IV-23),

Fluquinconazole (bekannt aus EP-A 0 183 458) der Formel (IV-24),

(3-25) Quinconazole (bekannt aus EP-A 0 183 458) der Formel (IV-25),

The formula (IV) comprises the following preferred compounds: Azaconazole (known from DE-A 25 51 560) of the formula (IV-1),

Etaconazole (known from DE-A 25 51 560) of the formula (IV-2),

Propiconazole (known from DE-A 25 51 560) of the formula (IV-3),

Difenoconazole (known from EP-A 0 112 284) of the formula (IV-4),

Bromuconazoles (known from EP-A 0 258 161) of the formula (IV-5),

Cyproconazole (known from DE-A 34 06 993) of the formula (IV-6),

Hexaconazole (known from DE-A 30 42 303) of the formula (IV-7),

Penconazole (known from DE-A 27 35 872) of the formula (IV-8),

Myclobutanil (known from EP-A 0 145 294) of the formula (IV-9),

Tetraconazole (known from EP-A 0 234 242) of the formula (IV-10),

Flutriafol (known from EP-A 0 015 756) of the formula (IV-11),

Epoxiconazoles (known from EP-A 0 196 038) of the formula (IV-12),

Flusilazole (known from EP-A 0 068 813) of the formula (IV-13),

Simeconazole (known from EP-A 0 537 957) of the formula (IV-14),

Prothioconazole (known from WO 96/16048) of the formula (IV-15),

Fenbuconazole (known from DE-A 37 21 786) of the formula (IV-16),

Tebuconazole (known from EP-A 0 040 345) of the formula (IV-17),

Ipconazole (known from EP-A 0 329 397) of the formula (IV-18),

Metconazole (known from EP-A 0 329 397) of the formula (IV-19),

Triticonazole (known from EP-A 0 378 953) of the formula (IV-20),

Bitertanol (known from DE-A 23 24 010) of the formula (IV-21),

Triadimenol (known from DE-A 23 24 010) of the formula (IV-22),

Triadimefon (known from DE-A 22 01 063) of the formula (IV-23),

Fluquinconazole (known from EP-A 0 183 458) of the formula (IV-24),

(3-25) quinconazole (known from EP-A 0 183 458) of the formula (IV-25),

fungizid wirksam ist.It is also known that Triazoxides (known from DE-A 28 02 488) of the formula (V),

fungicidally effective.

fungizid wirksam ist.Furthermore, it is known that silthiofam (known from WO 96/18631) of the formula (VI)

fungicidally effective.

In addition, it is known that penthiopyrad of formula (VII), known from EP 0 737 682 , fungicidal

The Effectiveness of all individual compounds is good, but leaves at low application rates in some cases to be desired.

It was now surprisingly found that mixtures consisting of at least three fungicides (Components A, B and C) have synergistic fungicidal effects, this means the effects of the mixtures is greater than the sum of the individual effects. There is therefore an unpredictable synergistic effect and not just an effect supplement.

If the active ingredients in the active compound combinations according to the invention in certain weight ratios are present, the synergistic effect is particularly evident. However, you can the weight ratios the active ingredients in the drug combinations in a relatively large area be varied. In general, the combinations according to the invention contain Active ingredients selected from categories A, B and C in the table below indicated preferred mixing ratios, wherein the mixing ratios on weight ratios based.

All are according to the invention listed in Table 1 Active substance mixtures consisting of at least three components A, B and C according to table 1.

The compounds of the general formula (I) are present in various stereoisomeric forms, which are described by the formulas (I _I ), (I _II ), (I _III ) and (I _IV ).

The invention, in particular the compounds (I-1), (I-2), (I-3) and (I-4) of component A, comprises all stereoisomeric forms of the general formula (I) which are represented by the formulas ( I _I ), (I _II ), (I _III ) and (I _IV ) are represented, in optically pure form or any mixing ratios to each other.

Preferred stereoisomers for racemates of the formula (I-4) are the trans compounds of the formulas (I _II -4) and (I _III -4).

In the following, preferred ratios of the four stereoisomers (I _I ), (I _II ), (I _III ) and (I _IV ) are given to each other.

Preference is given to mixtures in which in component A the proportion by weight of the two stereoisomers ( _II ) and ( _III ) is in total between 65 and 99%.

Preference is furthermore given to mixtures in which in component A the proportion by weight of the two stereoisomers (I _I ) and ( _IV ) is in total between 65 and 99%.

Particularly preferred are mixtures in which in component A the proportion by weight of the two stereoisomers (I _II -4) and (I _III -4) is in total between 65 and 99%.

The components A, B and C can be selected from the active ingredients listed in Table 1, wherein all combinations selected from the columns of the table are possible. Table 1

Prefers be the following agents for the selection of components A, B and C according to the following list:

Component A selected from:

• Compound (I-4)

Component B selected from:

• Azoxystrobin (II), Fludioxonil (III)

Component C selected from:

• Azaconazole (IV-1), etaconazole (IV-2), propiconazole (IV-3), Difenoconazole (IV-4), bromuconazole (IV-5), cyproconazole (IV-6), Hexaconazole (IV-7), penconazole (IV-8), myclobutanil (IV-9), tetraconazole (IV-10), flutriafol (IV-11), epoxiconazole (IV-12), flusilazole (IV-13), simeconazole (IV-14), prothioconazole (IV-15), fenbuconazole (IV-16), tebuconazole (IV-17), ipconazole (IV-18), metconazole (IV-19), Triticonazole (IV-20), bitertanol (IV-21), triadimenol (IV-22), Triadimefon (IV-23), fluquinconazole (IV-24), quinconazole (IV-25), Triazoxide (V), silthiofam (VI), penthiopyrad (VII).

Particularly preferred are the following active compound combinations according to Table 2, wherein all combinations selected from the columns of the table are possible. Table 2

Especially be the following combinations of the preferred components A, Called B and C. They are listed in Table 3, with one row of the table represents a particularly preferred combination.

Table 3

Especially The following active ingredients are preferred for the selection of the components A, B and C according to the table 4, with all combinations selected from the columns of the table possible are.

Table 4

Especially be the following combinations of the most preferred components A, B and C are listed in Table 5, with one row of the Table represents a particularly preferred combination.

Table 5

All Particularly preferred are the following active ingredients for the selection of the components A, B and C according to the table 6, with all combinations selected from the columns of the table possible are.

Table 6

Especially be the following combinations of the most preferred Called components A, B and C, they are listed in Table 7, wherein one line of the table is a particularly preferred combination represents.

Table 7

The preferred (a) and most preferred (b) mixing ratios of components A, B and C (A: B: C) are given in Table 8 below: Table 8

The active compound combinations according to the invention have a strong microbicidal action and can be used to combat undesirable Microorganisms, such as fungi and bacteria, in crop protection and in Material protection are used.

fungicides can plant protection be used to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

bactericidal can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae deploy.

By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-enumerated generic terms, are named:
Diseases caused by pathogens of powdery mildew such as
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 Gymnosporangium sabinae
Hemileia species, such as Hemileia vastatrix;
Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae;
Puccinia species, such as Puccinia recondita;
Uromyces species, such as Uromyces appendiculatus;
Diseases caused by pathogens of the group of Oomycetes 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 Pseudoperonospora humuli or
Pseudoperonospora cubensis;
Pythium species such as Pythium ultimum;
Leaf spot diseases and leaf withering, 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 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 gaminicola;
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 eg
Corticium species, such as Corticium gaminearum;
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 eg
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 such as
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 by eg
Aspergillus species, such as Aspergillus flavus;
Botrytis species, such as Botrytis cinerea;
Penicillium species such as Penicillium expansum;
Sclerotinia species, such as Sclerotinia sclerotiorum;
Verticilium species such as Verticilium alboatrum;
Seed and soil-borne rots and wilting, and seedling diseases, caused by eg
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 eg
Nectria species, such as Nectria galligena;
Wilting diseases caused by eg
Monilinia species, such as Monilinia laxa;
Deformations of leaves, flowers and fruits, caused by eg
Taphrina species, such as Taphrina deformans;
Degenerative diseases woody plants, caused by eg
Esca species, such as Phaemoniella clamydospora;
Flower and seed diseases, caused by eg
Botrytis species, such as Botrytis cinerea;
Diseases of plant tubers, caused by eg
Rhizoctonia species, such as Rhizoctonia 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 eg
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 at roots and stem base caused by eg
Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wilt, 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 irregulare, 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 good plant tolerance the drug combinations in the fight against plant diseases necessary concentrations allows treatment of whole plants (above-ground parts of plants and roots), of planting and seed, and the soil. The active compound combinations according to the invention can used for foliar application or as a mordant.

The good plant tolerance the useful agents in the control of plant diseases necessary concentrations allows treatment of the seed. The active compounds according to the invention can thus be used as a mordant.

One greater Part of damage to crops caused by phytopathogenic fungi is already caused by the infestation of the seed during storage and after the introduction of the seed into the soil as well as during and immediately after the germination of the plants. This phase is particularly critical as the Particularly sensitive to the roots and shoots of the growing plant are and already a small damage to the death of the whole plant to lead can. There is therefore a particular interest in the seed and the germinating plant by the use of suitable means protect.

The fight of phytopathogenic fungi that damage plants after emergence occurs primarily by the treatment of the soil and the above ground Plant parts with pesticides. Due to concerns about of a possible Influence of plant protection products on the environment and health of people and animals there are efforts, the amount of applied To reduce active ingredients.

The fight 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 treatments for seeds Problems that are not always solved satisfactorily can. So it is worthwhile, procedures for the protection of the seed and To develop the germinating plant, the additional application of pesticides make it redundant after sowing or after emergence of the plants or at least significantly reduce. It is still desirable to optimize the amount of active ingredient used to that the seed and the germinating plant from infestation by phytopathogenic Mushrooms best possible protected is, but without the plant itself by the active ingredient used to harm. In particular, seed treatment methods should also include involve intrinsic fungicidal properties of transgenic plants, for optimal protection of the seed and the germinating plant to achieve a minimum of pesticides.

The The present invention therefore more particularly relates to Method for protecting seed and germinating plants from the Infestation of phytopathogenic fungi by adding the seed with an agent according to the invention is treated.

The The invention also relates to the use of the agents according to the invention for the treatment of seed for the protection of seed and germinating Plant in front of phytopathogenic fungi.

Farther The invention relates to seed, which protects against phytopathogenic Mushrooms with an agent according to the invention was treated.

one the advantages of the present invention is that due to the particular systemic properties of the agents according to the invention the treatment of the seed with these means not only the seed itself, but also the resulting plants after the Protrusion against phytopathogenic fungi protects. In this way, the immediate treatment of the culture at the time of sowing or shortly then omitted.

As well it is to be regarded as advantageous that the mixtures according to the invention especially in transgenic seeds can be used.

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 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 CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) 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). Each having the desired properties ( "traits") conferring genes may also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD ^® (for example maize , cotton, soybeans), KnockOut ^® (for example maize), StarLink ^® (for example maize), Bollgard ^® (cotton), NuCOTN ^® (cotton) and NewLeaf ^® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are resistant under the trade names Roundup Ready ^® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link ^® (tolerance to phosphinotricin, for example oilseed rape), IMI ^® (tolerance Imidazolinone) and STS ^® (tolerance to sulfonylureas such as corn) are sold. 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 future or future marketed plant varieties with these or future developed genetic traits.

The agents according to the invention are suitable for the protection of seed of any plant variety that in agriculture, in the greenhouse, used in forestry or horticulture. In particular, acts these are seeds of cereals (such as wheat, barley, rye, Millet and oats), corn, cotton, soy, rice, potatoes, sunflower, Bean, coffee, turnip (for example, sugar beet and fodder beet), Peanut, rapeseed, canola and vegetables (like tomato, cucumber, onions and lettuce), turf and ornamental plants. Of particular importance is the treatment of the seed of cereals (like wheat, barley, rye and oats), potato, soy and rice to.

in the Within the scope of the present invention is the agent according to the invention applied alone or in a suitable formulation on the seed. Preferably, the seed is treated in a state in which it is so stable that no damage occur during treatment. In general, the treatment can of the seed at any time between harvesting and sowing respectively. Usually seed separated from the plant and used by flasks, Shells, stalks, shell Wool or pulp was freed. For example, seeds used, harvested, cleaned and up to a moisture content was dried below 15 wt .-%. Alternatively, seed can also be used used after drying, e.g. treated with water and then dried again.

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

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 the person skilled in the art and are described, for example, 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 less toxic and have good plant tolerance.

The active compound combinations according to the invention also have a strong restorative Effect in plants. They are therefore suitable for mobilization plant's own defenses against infestation by unwanted Microorganisms.

Under plant-strengthening (resistance-inducing) substances are in the present context to understand such substances that are capable of the immune system of plants to stimulate so that the treated plants at subsequent inoculation with unwanted microorganisms extensive resistance unfold against these microorganisms.

Under undesirable Microorganisms in the present case are phytopathogenic fungi, To understand bacteria and viruses. The substances according to the invention can So be used to plants within a period of time after the treatment against the infestation by the mentioned pathogens to protect. The period within which protection is provided extends in the Generally from 1 to 100 days, preferably 1 to 20 days after the treatment of the plants with the active substances respectively after sowing.

The good plant tolerance the drug combinations in the fight against plant diseases necessary concentrations allows treatment of above ground Plant parts, of plant and seed, and of the soil.

there let the active compound combinations according to the invention with particular success in combating cereal diseases, such as. against Tilletia caries, Ustilago nuda and diseases in dicotyledonous plants, e.g. against Rhizoctonia, Helminthosporium or Fusarium species, deploy.

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

The active compound combinations according to the invention can optionally in certain concentrations and application rates also as herbicides, for influencing plant growth, as well as for fight of animal pests be used.

According to the invention, all Plants and parts of plants are treated. Among plants are here understood all plants and plant populations, as desired and undesirable Wild plants or crops (including naturally occurring crops). Crops can Be plants by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or Combinations of these methods can be obtained, including transgenic ones Plants and including protected by plant variety rights or non-protectable plant varieties. Under plant parts are all above ground and underground Parts and organs of plants, such as shoot, leaf, flower and root By way of example, leaves, needles, stems, stems, flowers, fruiting bodies, fruits and Seeds as well as roots, tubers and rhizomes. To the plant parts belongs also harvested material as well as vegetative and generative propagation material, For example, cuttings, tubers, rhizomes, offshoots and seeds.

The treatment according to the invention of the plants and plant parts with the active ingredient combinations he follows directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, spraying, vaporizing, atomizing, spreading, brushing and propagating material, especially in seeds, further by single or multi-layer wrapping. In this case, the active ingredient combinations can be prepared before the treatment by mixing the individual active ingredients. Or the treatment is carried out successively by using first a phthalamide of the group (1) followed by the treatment with an active ingredient of the groups (2) to (24). However, it is also possible to first treat the plants or plant parts with an active compound of groups (2) to (24) and to attach the treatment with a phthalamide of group (1).

Furthermore have the active compound combinations according to the invention also very good antifungal effects. You own a lot broad antifungal activity spectrum, especially against dermatophytes and budworms, molds and diphasic fungi (e.g., against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species like Microsporon canis and audouinii. The listing of these mushrooms does not under any circumstances a restriction of the detectable mycotic spectrum, but has only illustrative Character.

The Drug combinations can as such, in the form of their formulations or the ones prepared from them Application forms, such as ready-to-use solutions, suspensions, wettable powders, Pastes, soluble Powder, dusts and granules are applied. The application happens in usual Way, e.g. by pouring, Spraying, spraying, Scattering, dusting, foaming, Brushing, etc. It is also possible to apply the active ingredients according to the ultra-low-volume method or the active ingredient preparation or the active ingredient itself in the soil to inject. It can also be the seed of the plants to be treated.

At the Use of the active compound combinations according to the invention as fungicides can the application rates depending on the type of application within a larger area be varied. In the treatment of plant parts are the Application rates of active ingredient 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 are generally between 0.001 and 50 grams per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the soil are the Application rates of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The listed Plants can particularly advantageous according to the invention with the drug mixtures be treated. The specified in the active ingredients or mixtures above Preferential ranges also apply to the treatment of these plants. Particularly emphasized is the Plant treatment with the compounds specifically listed herein or mixtures.

The Drug combinations can in the usual Formulations are transferred, like solutions, emulsions, Wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, Suspension emulsion concentrates, drug-impregnated Natural and synthetic substances as well as ultrafine encapsulations in polymers Substances.

These Formulations are prepared in a known manner, e.g. by Mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.

in the Traps of using water as diluent may be e.g. also organic solvents as auxiliary solvent be used. As liquid solvent are essentially in question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and 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, as well as water.

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 synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable 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 in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped Polymers such as gum arabic, polyvinyl alcohol, Polyvinyl acetate, as well as natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can mineral and vegetable oils be.

It can 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 are used.

The Formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active compound combinations according to the invention can in commercial Formulations and in those prepared from these formulations Forms of use mixed with other active substances, such as insecticides, Attractants, sterilants, bactericides, acaricides, nematicides, Fungicides, growth regulators or herbicides. To the insecticides count For example, phosphoric acid esters, carbamates, Carbonsäureester, chlorinated hydrocarbons, phenylureas, by microorganisms Fabrics u.a.

Also a mixture with other known active substances, such as herbicides or with fertilizers and growth regulators is possible.

The Treatment according to the invention the plants and plant parts with the active ingredients are made directly or by affecting their environment, habitat or storage space the usual Treatment methods, e.g. by dipping, spraying, evaporating, misting, Sprinkle, spread and propagate material, in particular in seeds, further by single or multi-layer wrapping.

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

Especially plants according to the invention are preferred the respective commercial or plant varieties in use.

ever according to plant species or plant varieties, their location and growth conditions (Floors, Climate, vegetation period, nutrition) can by the treatment according to the invention also superadditives ("Synergistic") effects occur. For example, reduced application rates and / or expansions of the Spectrum of action and / or an increase in the effect of the invention can be used Substances and agents, better plant growth, increased tolerance across from high or low temperatures, increased tolerance to dryness or against water or soil salt content, increased flowering efficiency, easier harvest, Acceleration of maturity, higher Crop yields, higher Quality and / or higher Nutritional value of Harvested products, higher Shelf life and / or workability of the harvested products possible, beyond the actually expected Go beyond effects.

The listed Plants can particularly advantageous according to the invention with the active substance mixtures according to the invention be treated. The preferred ranges given above for the mixtures apply also for the treatment of these plants. Particularly emphasized is the Plant treatment with the mixtures specifically mentioned herein.

The good fungicidal action of the active compound combinations according to the invention proceeds from the following give an example. While the individual active substances have weaknesses in the fungicidal action, the combinations show an effect that goes beyond a simple action summation.

One synergistic effect is always present in fungicides, though the fungicidal action of the active ingredient combinations is greater as the sum of the effects of the individually applied active ingredients.

und für eine Kombination aus 3 Wirkstoffen:

The expected effect for a given combination of 2 or 3 drugs can be calculated according to SR Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22) as follows:
If
X means the efficiency when using the active ingredient A in an application rate of m parts per million (ppm),
Y means the efficiency when using the active ingredient B in an application rate of n ppm,
Z means the efficiency when using the active ingredient C in an application rate of r ppm,
E _{1 means} the efficiency when using the active compounds A and B in application rates of m and n ppm, and
E _{2 means} the efficiency when using the active compounds A and B and C at application rates of m and n and r ppm,
then

and for a combination of 3 agents:

there the efficiency is determined in%. It means 0% efficiency, which corresponds to that of the controller, 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, ie there is a synergistic effect. In this case, the actual observed efficiency must be greater than the value calculated for the expected efficiencies E ₁ and E ₂ calculated from the formula given above.

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

Example A

Pyricularia oryzae test (in vitro) / microtiter plates

Of the Microtest in microtiter plates with Potato Dextrose Broth (PDB) as a liquid Test medium performed. The application of the active ingredients is carried out as a technical a.i., dissolved in acetone. For inoculation, a spore suspension of Pyricularia oryzae used. After 3 days of incubation in the dark and with shaking (10 Hz) becomes the light transmittance in every filled cavity the microtiter plates determined by means of a spectrophotometer.

there 0% means an efficiency equal to the growth in the controls matches while An efficiency of 100% means that no fungal growth is observed becomes.

Claims (15)

Active substance combination comprising: A) at least one compound of the general formula (I),

in which R ^{1 is} trifluoromethyl or difluoromethyl and R ^{2 is} hydrogen or methyl and B) at least one compound selected from the group azoxystrobin of the formula (II)

or fludioxonil of the formula (II),

and C) at least one compound selected from the group consisting of a triazole of the general formula (IV)

in which Q is hydrogen or SH, m is 0 or 1, R ^{13 is} hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy, R ^{14 is} hydrogen or chlorine, A ^{4 is} a direct bond, -CH ₂ -, - (CH ₂ ) ₂ -, -O-, is * -CH ₂ -CHR ¹⁷ - or * -CH = CR ¹⁷ -, wherein the bond marked with * is linked to the phenyl ring, and then R ¹⁵ and R ¹⁷ together for -CH ₂ -CH ₂ -CH [CH (CH ₃ ) ₂ ] - or -CH ₂ -CH ₂ -C (CH ₃ ) ₂ - stand, A ^{5 is} C or Si (silicon), A ⁴ also represents -N (R ¹⁷ ) - is and A ⁵ also together with R ¹⁵ and R ^{16 is} the group C = NR ¹⁸ , where R ¹⁷ and R ¹⁸ then together represent the group

R ^{15 is} hydrogen, hydroxy or cyano, R ^{16 is} 1-cyclopropylethyl, 1-chlorocyclopropyl, C ₁ -C ₄ -alkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₂ Haloalkoxy-C ₁ -C ₂ -alkyl, trimethylsilyl-C ₁ -C ₂ -alkyl, monofluorophenyl, or phenyl, R ¹⁵ and R ¹⁶ also together are -O-CH ₂ -CH (R ¹⁸ ) -O-, -O-CH ₂ -CH (R ¹⁸ ) -CH ₂ -, or -O-CH- (2-chlorophenyl) -, R ^{18 is} hydrogen, C ₁ -C ₄ -alkyl or bromine or triazoxide (V) , Silthiofam (VI), Penthiopyrad (VII) Active substance combinations according to Claim 1, in which component A is the same as compound (I-4)

component B is selected from azoxystrobin and fludioxonil and component C is selected from azaconazole (IV-1), etaconazole (IV-2), propiconazole (IV-3), difenoconazole (IV-4), bromuconazole (IV 5), cyproconazole (IV-6), hexaconazole (IV-7), penconazole (IV-8), myclobutanil (IV-9), tetraconazole (IV-10), flutriafol (IV-11), epoxiconazole (IV-12 ), Flusilazole (IV-13), simeconazole (IV-14), prothioconazole (IV-15), fenbuconazole (IV-16), tebuconazole (IV-17), ipconazole (IV-18), metconazole (IV-19) , Triticonazole (IV-20), Bitertanol (IV-21), Triadimenol (IV-22), Triadimefon (IV-23), Fluquinconazole (IV-24), Quinconazole (IV-25), Triazoxide (V), Silthiofam ( VI), Penthiopyrad (VII) Active substance combinations according to Claim 2, in which the Component C selected is from Difenoconazole (IV-4), Cyproconazole (IV-6), Tebuconazole (IV-17), triticonazole (IV-20), prothioconazole (IV-15), triadimenol (IV-22), fluquinconazole (IV-24), triazoxide (V), silthiofam (VI), ), Penthiopyrad (VII). Active substance combinations containing one of the combinations according to Table 3. Table 3

Active substance combinations containing one of the combinations according to Table 5. Table 5

Active substance combinations containing one of the combinations according to Table 7. Table 7

Containing synergistic drug combinations an active ingredient combination according to a the claims 1 to 6. Use of active ingredient combinations according to one the claims 1 to 9 to combat undesirable phytopathogenic fungi. Method of control undesirable phytopathogenic fungi, characterized in that one drug combinations according to claim 1 on the unwanted phytopathogenic fungi and / or their habitat and / or seed comprises applying. Process for the preparation of active substance combinations, characterized in that one comprises an agent according to one of claims 1 to 6 with surface active Mixtures and / or extenders mixed. Use of active ingredient combinations according to one the claims 1-6 for the treatment of seeds. Use of active ingredient combinations according to one the claims 1-6 for the treatment of transgenic plants. Use of active ingredient combinations according to one the claims 1-6 for the treatment of the seeds of transgenic plants. Seed, which with a combination of active ingredients according to one the claims 1-6 was treated. Active substance combinations according to Claim 2, in which, in component A, the proportion of the two stereoisomers (I _II -4) and (I _III -4)

65 to 99% by weight of the active ingredient.