WO2009071389A1 - Fungicide mixtures - Google Patents

Abstract

The present invention relates to fungicide mixtures, containing as the active components 1) azolyl methyloxirane of the general formula (I), wherein A is phenyl, which is substituted by an F and one additional substituent, selected from Cl, C1-C4-alkyl, C1-C4-halogen alkyl, and C1-C4-alkoxy, B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl, or furyl, or for phenyl, which is substituted by one to three of the following substituents: halogen, NO2, amino, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogen alkyl, C1-C4-halogen alkoxy, C1-C4-alkylamino, C1-C4-dialkyl amino, thio, or C1-C4-alkylthio, provided that B is not o-methyl phenyl, if A is 2-Chlor-4-fluorophenyl, and the acid addition or metal salts thereof compatible for plants, and 2) a fungicide compound Il as described in the application, the use of the fungicide mixtures for combating plant-pathological fungi, and agents containing the same.

Description

 Fungicidal mixtures

Fungicidal mixtures containing as active components

1) Azolylmethyloxirane of the general formula I.

worin

wherein

A is phenyl which is substituted by an F and another substituent selected from Cl, C _r C ₄ alkyl, Ci-C ₄ haloalkyl, and C _r C ₄ - alkoxy,

B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl or is phenyl which is alkyl substituted by one to three of the following substituents: halogen, NO _2, amino, Ci _-C4 -alkyl, Ci-C ₄ alkoxy, Ci-C ₄ haloalkyl, Ci-C ₄ - haloalkoxy, Ci-C ₄ alkylamino, Ci-C ₄ dialkylamino, thio, or Ci-C ₄ - alkylthio,

with the proviso that B is not o-methylphenyl when A is 2-chloro-4-fluorophenyl,

as well as their plant-tolerated acid addition or metal salts, and

2) a fungicidal compound II selected from

2.1) strobilurins, selected from

Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allylideneaminooxymethyl) -phenyl ) -2-methoxyimino-N-methyl-acetamide;

2.2) Carboxylic acid amides selected from

- carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kirala- xyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarbonyl, penthiopyrad, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- ( 1, 1, 3-trimethyl-indan-4-yl) nicotinamide, N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1 H- pyrazole-4-carboxamide, 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [2- (1,3-dimethyl-butyl) -phenyl] -amide, N- (4'-chloro) 3 ', 5-difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (4'-chloro-3', 5-difluoro-biphenyl-2-yl) yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3-trifluoromethyl-1-methyl- 1 H-pyrazole-4-carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3,1-Difluoro-4'-methyl-biphenyl-2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (2-bicyclopropyl-2-yl-phenyl) - 3-difluoromethyl-1-methyl-1H-pyrazole-4-ca amic acid amide, N- (cis-2-bicyclopropyl-2-yl-phenyl) -3-di-fluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (trans-2-bicyclopropyl-2-yl) phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (2'-fluoro-

4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl ) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole 4-carboxamides, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazoles-4-carboxamides, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl-1-methyl -1 H -pyrazole-4-carboxamide, N- (4 '- (trifluoro-methylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1 H -pyrazole-4-carboxamide, N' - (4 - (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methyl-formamidine, N '- (4- (4-fluoro-3-trifluoromethyl-phenoxy) -2 , 5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilany 1-propoxy) -phenyl) -N-ethyl-N-methylformamidine, N- (2 ', 4'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ', 4'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-

1 H-pyrazole-4-carboxamide, N- (2 ', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2', 5 ' -Dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3 ', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N- (3 ', 5'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3'-fluorobiphenyl-2 -yl) -3-difluoromethyl-1-methyl-

1 H -pyrazole-4-carboxamide, N- (3'-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2'-fluorobiphenyl-2-yl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2'-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N [2- (1,1,3,3,3-hexafluoropropoxy) -phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1) 2,2-tetrafluoroethoxy) -phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3 -dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, N- [1,2,3,4-tetrahydro-9- (1 - methylethyl) -1, 4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide;

- Carboxylic acid morpholides: Dimethomorph, Flumorph;

Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;

Other carboxamides: carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;

2.3) Azoles selected from - triazoles: azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, mycelobutanil, oxpoconazole, paclobutrazole , Penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] -triazol-1-yl ) cycloheptanol;

- imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizo- Ie;

Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- Other: Ethaboxam, Etridiazole, Hymexazole, 1- (4-Chloro-phenyl) -1- (propyn-2-yloxy) -3- (4- (3,4-dimethoxyphenyl) -isoxazol-5-yl) -propan-2-one, 2- (4-chloro-phenyl) -

N- [4- (3,4-dimethoxy-phenyl) -isoxazole-5-yl] -2-prop-2-ynyloxy-acetamide;

2.4) Nitrogen-containing heterocyclyl compounds selected from

Pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6-

Tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro-pyridine-2,6-dicarbonitrile, N- (1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2, 4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichloro-nicotinamide;

- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrimine, nitrapyrin, nuarimol, pyrimethanil;

- piperazines: triforins;

- Pyrroles: fludioxonil, fenpiclonil;

- Morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tride- morph; - piperidines: fenpropidine;

Dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;

non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhi- non, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester; - Other: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulphate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazid, pyroquilon, Quinoxyfen, triazoxide, tricyclazoles, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5 -α] pyidin, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1- (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H- benzoimidazole, 6- (3,4-dichlorophenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6- (4-tert-butylphenyl) -5 -methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methyl-6- (3,5,5-trimethyl-hexyl) - [1, 2,4 ] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-methyl- 5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-yl-amine, 6-ethyl-5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6- (3,5,5-trimethyl- hexyl) - [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-octyl-5-propyl- [1,2,4] triazolo [1,5-a] pyrimidine -7-yl-amine, 5-methoxymethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyimidin-7-ylamine, 6-octyl-5-trifluoromethyl- [1, 2,4 ] triazolo [1,5-a] pyrimidine-7 -ylamine and 5-trifluoromethyl-6- (3,5,5-trimethyl-hexyl) - [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine;

2.5) carbamates and dithiocarbamates selected from

Thio and dithiocarbamates: Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram;

- Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester ;

2.6) Other fungicides selected from

Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat); - antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;

Nitrophenyl derivatives:

Binapacryl, dicloran, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;

Organometallic compounds: Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;

Sulfur-containing heterocyclyl compounds: isoprothiolanes, dithianone;

Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;

Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalocyanine

Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide;

- Inorganic active substances: Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;

- Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (Cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluoro-phenyl) -methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl ) -N-ethyl-N-methylformamidine, N '- (4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (2 -Methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl -propoxy) -phenyl) -N-ethyl-N-methylformamidine, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl-acety-O-piperidine] -yl] -thiazole -carboxylic acid methyl (1, 2,3,4-tetrahydronaphthalen-1-yl) -amide, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidine-4 -yl} -thiazole-4-carboxylic acid-methyl- (R) -1, 2,3,4-tetrahydronaphthalene-1-yl-amide, acetic acid-6-tert-butyl-8-fluoro-2,3-dimethyl - Quinolin-4-yl-ester, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-ester

in a synergistically effective amount.

Furthermore, the invention relates to the use of the fungicidal mixtures for controlling phytopathogenic fungi and agents or compositions containing them.

Azolylmethyloxiranes of component 1, their preparation and their use in crop protection are known from WO2007147841 and the underlying EP 061 15936.4.

The active compounds mentioned above as component 2, their preparation and their action against harmful fungi are known (cf: http: //www.hclrss. Demon.co.uk/index.html; http://www.alanwood.net / pesticides /); they are commercially available. The compounds named after IUPAC, their preparation and their fungicidal action are also known (see Can. J. Plant Sci 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031;

A 226 917; EP-A 243 970; EP-A 256,503; EP-A 428 941; EP-A 532,022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE

19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503;

WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404;

WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583;

WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804;

WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772;

WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098;

WO 07/90624).

With regard to a reduction of the application rates and a broadening of the spectrum of action of the known compounds, the present invention The object of the invention is to provide an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied active substances.

Accordingly, the mixtures defined above were found. The present invention therefore also relates in particular to fungicidal compositions which comprise at least one compound of general formula I and at least one further fungicidal active ingredient (component 2), eg. One or more, e.g. 1 or 2 active substances of the abovementioned groups 2.1 to 2.6 and optionally one or more agriculturally suitable carriers. It has also been found that with simultaneous joint or separate application of the compound I and the compound II or when using the compound I and the compound II successively control fungi better than with the individual compounds (synergistic mixtures). With regard to a reduction of the application rates, these mixtures are of interest, since many with reduced total amount of active ingredients shown an improved activity against harmful fungi, especially for certain indications show. By simultaneous joint or separate application of the compound I with the compound II, the fungicidal activity is increased to a superadditive extent.

Common application within the meaning of this application means that the at least one compound I and the at least one other active ingredient at the same time at the site of action (ie the attacking plant-damaging fungi and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces) in an amount sufficient for effective control of fungal growth. This can be achieved by simultaneously applying the compounds I and at least one further active ingredient together in a common active ingredient preparation or in at least two separate active ingredient preparations or by applying the active ingredients one after the other at the site of action, wherein the time interval of the individual active substance applications is selected such that that the first applied active ingredient at the time of application of / the other drug / substances in sufficient amount is present at the site of action. The time sequence of the application of the active ingredients is of minor importance.

The compound I is able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them.

Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid. acid, phosphoric acid and nitric acid.

Examples of suitable organic acids are formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals such as phenyl and naphthyl carry one or two phosphoric acid radicals), wherein the alkyl or aryl radicals may carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

The metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others in consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period. The metals can be present in the various valences that belong to them.

In the definitions of the symbols given in the above formulas, collective terms have been used that are generally representative of the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl and the alkyl moieties of compound groups such as alkylamino: saturated, straight-chain or branched hydrocarbon radicals having preferably 1 to 4 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl and 1 , 1-dimethylethyl.

Haloalkyl: Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above. In one embodiment, the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine. In a further embodiment, the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred. Particular preference is given to (C 1 -C 4) -haloalkyl, more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;

Alkoxy: for an oxygen-bonded alkyl group as defined above, preferably having 1 to 4 carbon atoms. Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy.

Haloalkoxy: alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine. Examples of preferred haloalkoxy radicals are OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCHCl ₂ , OCCl ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxy, 1- (CH ₂ Cl) -2- chloroethoxy, 1- (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

Alkylthio: Alkyl as defined above attached via an S atom.

The compounds of formula I contain chiral centers and are generally obtained in the form of racemates or as mixtures of diastereomers of erythro and threo forms. The erythro and threo diastereomers can be separated in the inventive compounds, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers. As fungicidal agents it is possible to use both the uniform diastereomers or enantiomers and also their mixtures obtained in the synthesis. Enantiomeric pairs or enantiomers with cis-arrangement of ring B and triazolylmethyl substituent are preferred here.

The compounds I may be present in various crystal modifications whose biological activity may be different. These are included in the scope of the present invention. In the compounds of the formula I used according to the invention, the following meanings of the substituents, in each case alone or in combination, are particularly preferred. If appropriate, the preferred substituents or preferred combinations of substituents apply correspondingly to the precursors of the compounds according to the invention.

The substituent A is phenyl which is substituted by one F and one further substituent selected from Cl, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl and C 1 -C ₄ -alkoxy. According to one embodiment, one of the substituents is in the 4-position of the phenyl ring.

In another embodiment, the phenyl ring is substituted in the 2,4 position.

In another embodiment, A is phenyl substituted with one F and another substituent selected from Cl, methyl, trifluoromethyl and methoxy.

In a preferred embodiment, the substituent A is phenyl which is substituted by one F and one further substituent selected from methyl, methoxy and chlorine, so that a total of 12 substituents A1 to A12 of the following formulas result:

A10 A1 1 A12

In one embodiment, A is A1 to A5. In another embodiment, A is A1, A2 or A3.

According to a preferred embodiment, A is A1 or A2.

In another embodiment, A is A1.

In another embodiment, A is A2.

In another embodiment, A is A3. According to another embodiment, A stands for A4.

In another embodiment, A is A5.

In another embodiment, A is A6, A7, A8 or A9.

In another embodiment, A is A6, A8 or A9.

In a preferred embodiment, A is A8 or A9.

According to a particularly preferred embodiment, A is A9.

In another embodiment, A is A6.

In another embodiment, A is A7.

In another embodiment, A is A8.

In another embodiment, A is A10, A1 1 or A12.

According to a particularly preferred embodiment, A is A10.

According to another embodiment, A stands for A1 1.

In another embodiment, A is A12.

Another embodiment relates to compounds I in which B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl.

In a preferred embodiment, B is pyridyl or thienyl.

According to another preferred embodiment, B is pyridyl.

In a further embodiment of the present invention B is phenyl substituted by one to three of the following substituents: halogen, NO2, amino, Ci-C ₄ -alkyl, C ₄ -alkoxy, Ci-C _d-4 haloalkyl, _Ci-C4- Haloalkoxy, Ci-C ₄ alkylamino, CrC ₄ - dialkylamino, thio or Ci-C ₄ alkylthio is substituted.

In a further embodiment, B is phenyl, ₄ alkoxy, Ci-C ₄ haloalkyl or C substituted C ₄ -haloalkoxy by one to three of folic constricting substituents: halogen, Ci-C ₄ alkyl, C , In a preferred embodiment, B is phenyl substituted by one to three halogens.

In particular, with regard to their use, the compounds I according to the invention which are compiled in the following Tables 2 to 13 are preferred. The groups mentioned in the tables for a substituent are also considered individually, regardless of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.

Table 1

Table 2

Compounds of the formula I in which A is A1 and B in each case corresponds to a substituent of a line of Table 1, with the exception of 2-methylphenyl.

Table 3

Compounds of the formula I in which A is A2 and B in each case corresponds to a substituent of a row of Table 1.

Table 4

Compounds of the formula I in which A is A3 and B in each case corresponds to a substituent of a row of Table 1.

Table 5 Compounds of the formula I in which A is A4 and B in each case corresponds to a substituent of a row of Table 1.

Table 6

Compounds of the formula I in which A is A5 and B in each case corresponds to a substituent of a row of Table 1.

Table 7

Compounds of the formula I in which A is A6 and B in each case corresponds to a substituent of a row of Table 1.

Table 8

Compounds of the formula I in which A is A7 and B in each case corresponds to a substituent of a row of Table 1.

Table 9

Compounds of the formula I in which A is A8 and B in each case corresponds to a substituent of a row of Table 1.

Table 10 Compounds of the formula I, in which A is A9 and B in each case corresponds to a substituent of a row of Table 1.

Table 1 1

Compounds of the formula I in which A is A10 and B corresponds in each case to one substituent of one row of Table 1. Table 12

Compounds of the formula I in which A is A1 1 and B in each case corresponds to a substituent of a line of Table 1.

Table 13

Compounds of the formula I in which A is A12 and B corresponds in each case to one substituent of one row of Table 1.

In a preferred embodiment, the invention relates to fungicidal mixtures containing as active components

1) Azolylmethyloxirane of the general formula I, wherein

A represents phenyl which is tuiert substitutable by an F and another substituent selected from Cl, C _r C ₄ alkyl, Ci-C ₄ haloalkyl, and C _r C ₄ -

alkoxy,

B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl or phenyl which halogen by one to three of the following substituents, NO ₂ , amino, Ci-C ₄ alkyl, Ci-C ₄ alkoxy, Ci -C ₄ -haloalkyl, Ci-C ₄ -

Haloalkoxy, Ci-C ₄ alkylamino, Ci-C ₄ dialkylamino, thio, or Ci-C ₄ - alkylthio,

with the proviso that B is not o-methylphenyl when A is 2-chloro-4-fluorophenyl,

as well as their plant-tolerated acid addition or metal salts, and

2) a fungicidal compound II selected from 2.1) strobilurins selected from

Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (N- (4-methoxyphenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester;

2.2) Carboxylic acid amides selected from

- Carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isotianil, kiralaxyl, mepronil,

Metalaxyl, ofurace, oxadixyl, oxycarboxin, penthiopyrad, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- (1, 1, 3-tri- methyl-indan-4-yl) -nicotinamide, N- (3 \ 4'-dichloro-5-fluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, 5 -Fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [2- (1, 3-dimethyl-butyl) -phenyl] -amide, N- (4'-chloro-3 ', 5- difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (4'-chloro-3 ', 5-difluorobiphenyl-2-yl) -3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ', 4'-

Dichloro-5-fluoro-biphenyl-2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl-2 -yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl-2-yl) -3-trifluoromethyl-1-methyl 1-H-pyrazole-4-carboxylic acid amide, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-2-bicyclopropyl) 2-yl-phenyl) -3-di-fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl- 1 H-pyrazole-4-carboxylic acid amide, N- (2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl- 2-yl) -1-methyl-3-difluoromethyl

1 H-pyrazole-4-carboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ' , 4 ', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl 1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoro-methylthio) -biphenyl-2-yl) -1-methyl-3-trifluoromethyl-

1 H-pyrazole-4-carboxamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (4 (4-fluoro-3-trifluoromethylphenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl) propoxy) -phenyl) -N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine;

- Carboxylic acid morpholides: Dimethomorph, Flumorph;

Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide; Other carboxamides: carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;

2.3) Azoles selected from

- triazoles: azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole,

Flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, mycelobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro -phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol; - imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizo- Ie;

Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole, 1- (4-Chloro-phenyl) -1- (propyn-2-yloxy) -3- (4- (3,4-dimethoxyphenyl) -isoxazol-5-yl) -propan-2-one;

2.4) Nitrogen-containing heterocyclyl compounds selected from - pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6- Tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro-pyridine-2,6-di-carbonitrile, N- (1 - (S-bromo-S-chloro-pyridin ^ -yO-ethyl ^^ - dichloro -nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichloro-nicotinamide;

- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrimine, nitrapyrin, nuarimol, pyrimethanil;

- Pyrroles: fludioxonil, fenpiclonil;

- Morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tride- morph;

Dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin; - others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquatemethylsulphate, famoxadone, fenamidone, fenoxanil, fenpropidin, folpet, octhilinone , Oxolinic acid, piperine, samplesazoles, proquinazide, pyroquilon, quinoxyfen, triazoxide, tricyclazoles, triforines, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6-iodo-3-propyl-chromen-4-one;

2.5) carbamates and dithiocarbamates selected from

Thio and dithiocarbamates: Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; - Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester ;

2.6) Other fungicides selected from - guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat);

- antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;

Nitrophenyl derivatives: binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;

Organometallic compounds: Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;

Sulfur-containing heterocyclyl compounds: isoprothiolanes, dithianone;

Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;

Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalocyanine Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide;

- Inorganic active substances: Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;

- Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluorophenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - 4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) ) -phenyl) -N-ethyl-N-methylformamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine

in a synergistically effective amount.

Preferred compounds II are selected from azoxystrobin, kresoxim-methyl, picoxystrobin, pyraclostrobin and trifloxystrobin.

Further preferred compounds II are selected from azoxystrobin, kresoximethyl, pyraclostrobin and trifloxystrobin.

Preferred compounds II are also carboxin, bixafen, penthiopyrad, pyrimidinedione, metalaxyl, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole 4-carboxamide, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-bicyclopropyl-2-yl-phenyl) -3 -difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- ( 2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'- trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl -1 H -pyrazole-4-carboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (trifluoromethylthio) biphenyl-2-yl) -3- difluoromet hyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoro-methylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methyl-formamidine, N' - (4- (4-fluoro-3-trifluoromethyl -phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl -N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine. Preferred compounds II are selected bixafen, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (cis-bicyclopropyl-2-yl-phenyl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl- 3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N - (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoromethylthio) biphenyl-2-yl) -3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoromethylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4 -carboxamide e, N '- (4- (4-chloro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (4- (4-fluoro 3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine.

Preferred compounds II are selected from cyproconazole, difenoconazole, epoxiconazole, flusilazole, flutriafol, myclobutanil, metconazole, propiconazole, prothioconazole, tebuconazole, tetraconazole, prochloraz.

Preferred compounds II are selected from cyproconazole, epoxiconazole, metocynazole, propiconazole, prothioconazole, tebuconazole, tetraconazole, prochloraz.

Preferred compounds II are selected from carbendazim, thiabendazole, cyprindinil, fludioxonil, fenpropimorph, captan, fenpropidin, thiram, chlorothalonil, thiphanate-methyl, sulfur, copper hydroxide, metrafenone and spiroxamine.

Preferred compounds II are selected from carbendazim, fenpropimorph and metrafenone.

In a preferred embodiment, the compound II is selected from epoxiconazole, metconazole, myclobutanil, carbendiazim, captan, metrafenone, spiroxamine, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H pyrazole-4-carboxylic acid amide and N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide.

Preference is given to compositions of a compound I (component 1) with at least one active compound from group 2.1) (component 2) of strobilurins and especially selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, Orysastrobin, Picoxystrobin, Pyraclostrobin and Trifloxystrobin.

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from the group 2.2 (component 2) of the carboxamides and especially selected from hexhexamide, metalaxyl, mefenoxam, ofuracene, dimethomorph, flumorph, fluopicolide (picobenzamide) , Zoxamide, carpropamide and mandipropamide.

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from the group 2.3. (Component 2) of the azo and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluconconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, Benomyl, carbendazim and ethaboxam.

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from group 2.4 (component 2) of the nitrogen-containing heterocyclyl compounds and more particularly selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph , Tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenami- don, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen. Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from the group 2.5 (component 2) of the carambamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalacarb, flubenthiavalicarb and propamocarb.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from the fungicides of group 2.6 (component 2) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and their salts, Chlorothalonil, dichlofluanid, thiophosphate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6 -trifluorophenyl) - [1, 2,4] -triazolo [1,5-a] pyrimidine.

Preference is also given to the mixtures and combination partners mentioned in the application examples.

Preferably, the present invention further relates to the compositions listed in Table A, wherein in each case one row of Table A corresponds to a fungicidal composition comprising a compound of formula I (component 1), which is preferably one of the compounds described herein as preferred, and each further active compound II (component 2) indicated in the respective line. According to one embodiment of the invention, component 1 in each row of Table 2 is in each case one of the compounds of the formula I which are specifically individualized in Tables 1 to 13, preferably in Tables 1 to 7. Table A

The mixtures of the compounds I and II (= mixtures according to the invention) and their compositions according to the invention are suitable as fungicides for combating harmful fungi. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, which in particular from the classes of Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. In addition, they are suitable for controlling fungi that attack, among other things, the wood or the roots of plants.

Of particular importance are the mixtures of the compounds I and II (= mixtures according to the invention) and their compositions according to the invention for combating a large number of pathogenic fungi on various crop plants, such as cereals, eg. Wheat, rye, barley, triticale, oats or rice; Beets, z. Sugar or fodder beets; Kernel, stone and berry fruits, z. Apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; Legumes, z. Beans, lentils, peas, alfalfa or soybeans; Oil plants, e.g. Rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palm, peanuts or soya; Cucurbits, z. Pumpkins, cucumbers or melons; Fiber plants, z. Cotton, flax, hemp or jute; Citrus fruits, z. Oranges, lemons, grapefruit or mandarins; Vegetables, z. Spinach, salad, asparagus, Cabbages, carrots, onions, tomatoes, potatoes, squash or paprika; Laurel family, z. Avocados, cinnamon or camphor; Energy and raw material plants, eg. Corn, soy, wheat, rapeseed, sugarcane or oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (table and grapes); Hop; Grass, z. B. lawn; Rubber plants; Ornamental and forest plants, z. As flowers, shrubs, deciduous and coniferous trees and on the propagation material, for. B. seeds, and the crop of these plants.

Preferably, the mixtures of the compounds I and II (= mixtures according to the invention) or their compositions according to the invention for combating a variety of fungal pathogens in crops, z. Potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugarcane; Fruit, vine and ornamental plants and vegetables, eg. As cucumbers, tomatoes, beans and pumpkins and on the propagation material, for. As seeds, and the crop of these plants used. The term plant propagating materials includes all generative parts of the plant, e.g. As seeds, and vegetative plant parts, such as cuttings and tubers (eg., Potatoes), which can be used to propagate a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts, including seedlings and seedlings, which are transplanted after germination or emergence. The young plants can be treated by a partial or complete treatment, eg. B. by immersion or pouring, are protected from harmful fungi.

The treatment of plant propagation materials with the mixtures of the compounds I and II (= mixtures according to the invention) or their compositions according to the invention is used for controlling a multiplicity of fungal pathogens in cereal crops, eg. Wheat, rye, barley or oats; Rice, corn, cotton and soy used.

The term "crops" also includes those plants which have been modified by breeding, mutagenesis or genetic engineering methods, including biotechnological agricultural products currently on the market or under development (see for example http://www.bio.org/speeches/pubs/ er / agri_products .asp). Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant. Such genetic engineering also includes post-translational modifications of proteins, oligo- or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.

By way of example, plants may be mentioned which, by means of breeding and genetic engineering measures, tolerate certain types of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) -I inhibitors, such as, for example, As sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (eg. US Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03 / 14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024). By breeding and Mutagene- se was z. B. Clearfield ^® rapeseed (BASF SE, Germany) produced, the tolerance to imidazolinones, z. As imazamox, has. Using genetic engineering methods, crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name rou- dupReady ^® (glyphosate-resistant, Monsanto, USA) and Liberty Link ^® (Glufosinat- resistant, Bayer CropScience, Germany) are available.

Furthermore, plants are included which, with the aid of genetic engineering measures one or more toxins, eg. B. those from the bacterial strain Bacillus produce. Toxins produced by such genetically engineered plants include e.g. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. Eg from Streptomyces; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, e.g. 3-hydroxy steroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blocker, e.g. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and

WO 03/52073 discloses. The methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above. Numerous of the aforementioned toxins confer on the plants that produce them tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and

Butterflies (Lepidoptera) and nematodes (Nematoda). Genetically modified plants that produce one or more genes that code for insecticidal toxins. are zuz. As described in the publications mentioned above and partly commercially available, such as. B. YieldGard ^® (corn cultivars producing the toxin CrylAb), YieldGard ^® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ^® (corn cultivars producing the toxin Cry9c), Herculex ^® RW (corn cultivars produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT]); NuCOTN ^® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ^® I (cotton cultivars producing the toxin CrylAc), Bollgard ^® Il (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIP COT ^® (cotton cultivars producing a VIP-toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt Xtra ^®, NatureGard® ^®, KnockOut ^®, BiteGard ^®, Protec ta ^®, Bt11 (z. B. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which the toxin CrylAb and the PAT enzyme MIR604 from Syngenta Seeds SAS, France (maize varieties producing a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe SA, products (maize varieties producing the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties that produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the toxin Cryl F and the PAT enzyme).

Furthermore, plants are included, which produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as. B. so-called pathogenesis-related proteins (PR proteins, see EP-A O 392 225), resistance proteins (eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (For example, potato varieties that are resistant to bacteria such as Erwinia amylvora through the production of this protein).

Furthermore, plants are included whose productivity has been improved by genetic engineering methods by z. For example, yield (eg biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.

Furthermore, plants are included whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z. As oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ^® - rape, DOW Agro Sciences, Canada.) Produce.

Furthermore, plants are included, which have been modified for the improved production of raw materials by means of genetic engineering methods by z. B. the amylopectin content of potatoes (Amflora ^® potato, BASF SE, Germany) was increased.

Especially suitable are the mixtures of the compounds I and II (= mixtures according to the invention) or their compositions according to the invention for controlling of the following plant diseases:

Albugo spp. (White rust) on ornamental plants, vegetable crops (eg A. Candida) and sunflowers (eg BA tragopogonis); Alternaria spp. (Blackness, black spotiness) on vegetables, oilseed rape (for example BA brassicola or A. brassicae), sugar beet (for example BA tenuis), fruit, rice, soybeans and on potatoes (eg A. solani or A. alternata) and tomatoes (eg BA solani or A. alternata) and Alternaria spp. (Earwires) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg. BA tritici (leaf drought) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (Teleomorph: Cochliobolus spp.) Z. B. leaf spot diseases (D. maydis and B. zeicola) on maize, e.g. B. brown spot (B. sorokiniana) on cereals and B. B. oryzae on rice and on lawn; Blumeria (formerly: Erysiphe) graminis (powdery mildew) on cereals (eg wheat or barley); Botryosphaeria spp. ('Black Dead Arm Disease') on vines (eg BB obtusa); Botrytis cinerea (Teleomorph: Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z. BC ulmi (elm dying, Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spot) on maize (eg BC zeae-maydis), rice, sugar beets (eg BC beticola), sugarcane, vegetables, coffee, soybeans (eg BC sojina or C. kikuchii) and rice; Cladosporium spp. on tomato (eg BC fulvum: velvet spot disease) and cereals, eg. BC herbarum (earwax) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (for example BC carbonum), cereals (for example B. sativus, anamorph: B. sorokinia-na: brown spot) and rice (for example BC miyabeanus, anamorph: H. oryzae); Colletotricum (teleomorph: Glomerella) spp. (Burning stains, anthracnose) on cotton (eg BC gossypii), corn (eg BC graminicola: stalk rot and stinging spots), soft fruit, potatoes (eg BC coccodes: wilting), beans (eg BC lindemuthianum) and soybeans (eg. BC truncatum); Corticium spp., Z. BC sasakii (leaf sheath burn) on rice; Corynespora cassiicola (leaf spot) on soybeans and ornamental plants; Cycloconium spp., Z. BC oleaginum on olive; Cylindrocarpon spp. (for example, fruit tree crayfish or vine dying, Teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (eg C. liriodendri, Teleomorph: Neonectria liriodendri, 'Black Foot Disease') and many ornamental shrubs; Dematophora (Teleomorph: Rosellinia) necatrix (root / stem rot) on soybeans; Diaporthe spp. z. BD phaseolorum (stalk disease) on soybeans; Drechslera (Syn. Helminthosporium, Teleomorph: Pyrenophora) spp. on corn, cereals such as barley (eg BD teres, nettles) and wheat (eg BD tritici- repentis: DTR leaf drought), rice and turf; Esca disease (grapevine dying, apoplexy) on grapevine caused by Formitiporia (Syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe spp. on nuclear (E. pyri) and soft fruit (E. veneta: burning spots) and grapevine (E. ampelina: Focal spots); Entyloma oryzae (leaf sting) on rice; Epicoccum spp. (Earwires) on wheat; Erysiphe spp. (Powdery mildew) on sugar beet (E. betae), vegetables (eg BE pisi), such as cucumber (for example BE cichoracearum) and cabbage plants, such as rapeseed (for example, B. cruciferarum); Eutypa lata (Eutypa crab or extinction, anamorphic Cytosporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental shrubs; Exserohilum (Syn. Helminthosporium) spp. on maize (eg BE turcicum); Fusarium (Teleomorph: Gibberella) spp. (Wilt, root and stalk rot) on various plants, such. BF graminearum or F. culmorum (root rot and Tauboder whiteness) on cereals (eg wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on maize; Gaeumannomyces graminis (blackleg) on cereals (eg wheat or barley) and maize; Gibberella spp. cereals (eg BG zeae) and rice (eg BG fujikuroi: Bakanae disease); Glomerella cingulata on grapevine, pome fruit and other plants and G. gossypii on cotton; Grainstaining complex of rice; Guignardia bidwellii (black rot) on grapevine; Gymnosporangium spp. on rosaceae and juniper, eg. BG sabinae (pear grid) on pears; Helminthosporium spp. (Syn. Drechslera, Teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., E.g. BH vastatrix (coffee leaf rust) of coffee; Isariopsis clavispora (Syn. Cladosporium vitis) on grapevine; Macrophomina phasolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Microsium (Syn. Fusarium) nivale (snow mold) on cereals (eg wheat or

Barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., Z. BM laxa, M. fructicola and M. fructigena (flower and lace drought) on stone fruits and other rosaceae; Mycosphaerella spp. on cereals, bananas, berry fruits and peanuts, such as. BM graminicola (Anamorph: Septoria tritici, Septoria leaf drought) on wheat or M. fijiensis (Black sigatoka disease) on bananas; Peronospora spp. (Downy mildew) on cabbage (for example BP brassicae), oilseed rape (for example P. parasitica), onion plants (for example B. destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phallophora spp. z. On grapevines (eg BP tracheiphila and P. tetraspora) and soybeans (eg BP gregata: stalk disease); Phoma Hungary (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spots) on sugar beet; Phomopsis spp. on sunflowers, grapevine (eg BP viticola: black spot disease) and soybeans (eg stalk rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora spp. (Wilt, root, leaf, stem and fruit rot) on various plants, such as on paprika and cucurbits (eg BP capsici), soybeans (eg BP megasperma, Syn. P. sojae), potatoes and tomatoes (eg. BP infestans: herbaceous and brown rot) and deciduous trees (eg BP ramorum: sudden oak mortality); Plasmodiophora brassicae (cabbage hernia) on cabbage, oilseed rape, radish and other plants; Plasmopara spp., E.g. BP viticola (vine peronospora, fawn powdery mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (Powdery mildew) of rosaceae, hops, kernels and berries, eg. BP leucotricha to apple; Polymyxa spp., Z. Cereals such as barley and wheat (P. graminis) and beet (P.betae) and the viral diseases conferred thereby; Pseudocercosporella herpotrichoides (straw break, teleomorph: Tapesia yallundae) on cereals, e.g. Wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. BP cubensis on cucurbits or P. humili on hops; Pseudo-pezicula tracheiphila (red burner, anamorph: Phialophora) on grapevine; Puccinia spp. (Rust disease) on various plants, eg. BP triticina (wheat brown rust), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (black rust) or P. recondita (rye brown rust) on cereals, such as. Wheat, barley or rye, and asparagus (eg BP asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (leaf drought) on wheat or P. teres (netted spots) on barley; Pyricularia spp., E.g. BP oryzae (Teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and crops; Pythium spp. (Turnip disease) on turf, rice, corn, wheat, cotton, oilseed rape, sunflower, sugar beets, vegetables and other plants (eg BP ultimum or P. aphanidermatum); Ramularia spp., Z. BR collo-cygni (speckled disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants, eg. BR solani (root / stem rot) on soybeans, R. solani (leaf-sheathing) on rice or R. cerealis (pointed eye-spot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevine and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (Stem or white rot) in vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotium rum) and soybeans (eg BS rolfsii); Septoria spp. on different plants, eg. BS glycines (leaf spot) on soybeans, S. tritici (Septoria leaf drought) on wheat and S. (Syn. Stagonospora) nodorum (leaf and spelled tan) on cereals; Uncinula (Syn. Erysiphe) necator (powdery mildew, anamorphic: Oidium tuckeri) on grapevine; Sexspaeria spp. (Leaf spot) on corn (for example, S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (Dust fires) on maize, (for example BS reiliana: flask brandy), millet and sugarcane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powder scab) on potatoes and the viral diseases transmitted thereby; Stagonospora spp. on cereals, z. BS nodorum (leaf and tan, Teleomorph: Leptosphaeria [Syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato cancer); Taphrina spp., Z. BT deformans (curling disease) on peach and T. pruni (pocket disease) on plums; Thielaviopsis spp. (Black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, eg. BT basicola (Syn: Chalara elegans); Tilletia spp. (Stone or Stinkbrand) of cereals, such. BT tritici (Syn. T. caries, Weizensteinbrand) and T. controversa (Zwergsteinbrand) on wheat; Typhula incarnata (snow rot) on barley or wheat; Urocystis spp., E.g. BU occulta (stalk brandy) on rye; Uromyces spp. (Rust) on vegetables, such as beans (for example, appendiculatus appendix, Syn. U. phaseoli) and sugar beet (for example, Betae); Ustilago spp. (Flotation) at treide (for example BU nuda and U. avaenae), maize (for example BU maydis: maize buckthorn brandy) and sugarcane; Venturia spp. (Scab) on apples (eg BV inaequalis) and pears; and Verticillium spp. (Deciduous and cloudy wilt) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and crops, such. BV dahliae on strawberries, rapeseed, potatoes and tomatoes.

The mixtures of compounds I and II (= mixtures according to the invention) and their compositions according to the invention are also suitable for controlling harmful fungi in the protection of materials and buildings (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products , In wood and building protection, particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.

The mixtures of the compounds I and II (= mixtures according to the invention) and their compositions according to the invention are suitable for increasing plant health. In addition, the invention relates to a method for increasing the plant health, by the plants, the plant propagating material and / or the place where the plants grow or grow, with an effective amount of the mixtures of the compounds I and II (= mixtures according to the invention ) or their compositions according to the invention. The term "plant health" includes those conditions of a plant and / or its crop which are determined by different indicators individually or in combination with each other, such as yield (eg increased biomass and / or increased content of utilizable ingredients), Plant vitality (eg, increased plant growth and / or greener leaves), quality (eg, increased content or composition of certain ingredients), and tolerance to biotic and / or abiotic stress. These plant health status indicators referred to herein may be independent or mutually exclusive.

The compounds I and II can be applied simultaneously, jointly or separately or in succession, the sequence in the case of separate application generally having no effect on the control result. The process for controlling harmful fungi is carried out by the separate or combined application of the compound I and the compound II or the mixtures of the compound I and the compound II by spraying or dusting the seeds, the plants or the Soils before or after sowing the plants or before or after emergence of the plants.

The active compounds I and II can also be used in the form of their agriculturally acceptable salts. Usually come for alkali or alkaline earth salts, such as sodium, potassium or calcium salts in question, or other salts, as described in this application for compounds of formula I.

The mixtures of the compounds I and II (= mixtures according to the invention) are used as such or in the form of a composition by mixing the harmful fungi, their habitat or the plants to be protected against fungal attack, plant propagation materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I. The application may be both before and after the infection of the plants, plant propagation materials, eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.

Plant propagation materials can be treated preventively together with or even before sowing or together with or even before transplanting with mixtures of the compounds I and II (= mixtures according to the invention) or with compositions according to the invention thereof.

In addition, the invention relates to agrochemical compositions containing a solvent or solid carrier and at least one compound I and at least one compound II (= compositions according to the invention), and the use of these compositions for controlling harmful fungi. The invention therefore also comprises agents or agrochemical compositions which contain a solid or liquid carrier and a fungicidal mixture according to the invention. The term "liquid carrier" is used in this context synonymous with solvents.

An agrochemical composition contains a fungicidally effective amount of a mixture of the compounds I and II (= mixtures according to the invention). The term "effective amount" means an amount of the agrochemical composition or the mixture of compounds I and II which is sufficient for controlling harmful fungi on crop plants or in the protection of materials and buildings and does not lead to considerable damage to the treated crop plants Such amount may vary within a wide range and is influenced by numerous factors, such as the harmful fungus to be controlled, the particular crop or material being treated, climatic conditions and compounds.

In binary mixtures, ie compositions according to the invention which contain a compound I and a further active ingredient, for example an active compound from groups 2.1 to 2.6, the weight ratio of compound I to the further active ingredient usually in the range of 1: 100 to 100: 1, often in the range of 1:50 to 50: 1, preferably in the range of 1:20 to 20: 1, more preferably in the range of 1:10 to 10: 1, in particular in the range of 1: 3 to 3: 1.

If desired, the further active components are added to the mixture of compound I and compound II in a ratio of from 20: 1 to 1:20.

The components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the kit of parts and reused.

In one embodiment of the invention, the kits (kits) may contain one or more, even all, components that can be used to prepare an agrochemical composition of the invention. For example, these kits may contain one or more fungicidal component (s) and / or an adjuvant component and / or an insecticidal component and / or a growth regulator component and / or a herbicide. One or more components may be combined or pre-formulated. In embodiments where more than two components are provided in a kit, the components may be combined together and packaged in a single container such as a vessel, bottle, can, bag, sack or canister. In other embodiments, two or more components of a kit may be packaged separately, i. H. not pre-formulated or mixed. Kits may contain one or more separate containers such as containers, bottles, cans, bags, sacks or canisters, each container containing a separate component of the agrochemical composition. The components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the "kit of parts" and reused. In both forms, one component can be used separately or together with the other components or as part of a kit of parts according to the invention for the preparation of the mixture according to the invention. The user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane. In this case, the agrochemical composition with water and / or buffer is brought to the desired application concentration, optionally further adjuvants are added, and thus the ready-spray mixture or the agrochemical composition according to the invention is obtained. Usually, 50 to 500 liters of ready-spray mixture per hectare of agricultural land, preferably 100 to 400 liters.

In one embodiment, the user may include individual components such as For example, parts of a kit or a mixture of two or three of the composition according to the invention itself mix in the spray tank and optionally add further auxiliaries (tank mix).

In a further embodiment, the user can select both individual components ten of the composition according to the invention as well as partially premixed components, for example components containing compounds I and / or active compounds from groups 2.1 to 2.6, mix in the spray tank and optionally add further auxiliaries (tank mix). In a further embodiment, the user can use both individual components of the composition according to the invention and partially premixed components, for example components comprising compounds I and / or active compounds from groups 2.1 to 2.6, together (for example as a tank mix) or in succession.

Depending on the nature of the compounds and the desired effect, the application rates of the mixtures according to the invention are between 0.001 and 2.0 kg of active ingredient mixture per ha, preferably between 0.005 and 2 kg per ha, more preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha.

The application rates for the compound I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha. The application rates for the active compound II are correspondingly generally 1 to 2000 g / ha, preferably 10 to 900 g / ha, in particular 40 to 500 g / ha.

In the treatment of plant propagation materials, eg. B. State, are generally amounts of drug mixtures from 0.1 to 1000 g / 100 kg of propagating material or seed, preferably 1 to 1000 g / 100 kg, more preferably 1 to 100 g / 100 kg, especially 5 to 100 g / 100 kg used. When used in material or storage protection, the application rate of active ingredient mixture depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.

The mixtures according to the invention of the compounds I and II and their N-oxides and salts, or the compound I and the compound II and their respective N-oxides and salts can be converted into the types customary for agrochemical compositions, eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type of composition depends on the respective intended use; It should in any case ensure a fine and uniform distribution of the compound according to the invention.

The term "agent" in this context is used synonymously with the term "composition", in particular "agrochemical composition", and "formulation".

Examples of composition types are suspensions (SC, OD, FS), pastes, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which may either be soluble or dispersible in water or gels for the treatment of plant propagation materials such as seeds (GF). In general, the composition types (eg SC, OD, FS, WG, SG,

WP, SP, SS, WS, GF) diluted. Composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.

The compounds I and II can be present in a common composition or in separate compositions. The type and preparation of the particular composition corresponds to the type and preparation as generally described for compositions herein.

The agrochemical compositions are prepared in a known manner (see, for example, US 3,060,084, EP-A 707,445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill, New York, 1963, 8-57 and et seq., WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (John Wiley & Sons, New York, 1961), Hance et al .: Weed Control Handbook (8th Ed., Blackwell Scientific Publications, Oxford, 1989) and Mollet, H. and Grubemann, A. : Formulation technology (Wiley VCH Verlag, Weinheim, 2001).

The agrochemical compositions can furthermore also contain auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.

Examples of suitable auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment). Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphtha line and derivatives thereof, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, gycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters and highly polar solvents, for example amines such as N-methylpyrrolidone into consideration. In principle, solvent mixtures and mixtures of the abovementioned solvents and water can also be used. Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, cellulose powder or other solid carriers.

Suitable surface-active substances (adjuvants, wetting, adhesion, dispersing or emulsifying agents) are the alkali metal, alkaline earth metal, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ^® grades, Borregaard, Norway), phenol, naphtha lin (Morwet ^® types, Akzo Nobel, USA) and dibutyl (nekal ^® - types, BASF, Germany), and of fatty acids , Alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with Phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecylalcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulphite liquors and Proteins, denatured proteins, polysaccharides (eg methylc ellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol ^® types, Clariant, Switzerland), poly-carboxylate (Sokalan ^® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lu pamin ^® types, BASF, Germany), polyethylenimine (Lupasol ^® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.

Examples of thickeners (ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion) are polysaccharides and organic and inorganic see layered minerals, such as xanthan gum (Kelzan ^®, CP Kelco, U.S.A.), Rhodopol ^® 23 (Rhodia, France) or Veegum ^® (RT Vanderbilt, USA) or attaclay ^® (Engelhard Corp., NJ, USA).

Bactericides may be added to stabilize the composition. Examples of bactericides are those based on dichlorophen and benzyl alcohol hemiformal (Proxel ^®.. Of Messrs. ICI or Acetide ^® RS from Thor Chemie and Kathon ^® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acetide ^® MBS Fa. Thor Chemie).

Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin. Examples of defoamers are silicone emulsions (such as, for example, ^Silikon® SRE, Wacker,

Germany or Rhodorsil ^®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Examples of colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are those under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, Pigment Blue 15: 4, Pigment Blue 15: 3, Pigment Blue 15: 2, Pigment Blue 15: 1, Pigment Blue 80, Pigment yel- low 1, pigment yellow 13, pigment red 48: 2, pigment red 48: 1, pigment red 57: 1, pigment Pigment Red 43, Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108 known dyes and pigments. Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and

Cellulose ethers (Tylose ^®, Shin-Etsu, Japan).

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, there are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the compounds I and II and, where present, other active substances with at least one solid carrier.

Granules, for. As coated, impregnated and homogeneous granules can be prepared by binding the active compounds or drug mixtures to at least one solid carrier. Solid carriers are z. As mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate , Ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.

Examples of composition types are: 1. Compositions for dilution in water i) Water-soluble concentrates (SL, LS)

10 parts by weight of the active compounds or active substance mixtures are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a composition with 10 wt .-% active ingredient content. ii) Dispersible Concentrates (DC)

20 parts by weight of the active compounds or active substance mixtures are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water gives a dispersion. The active ingredient content is 20% by weight iii) Emulsifiable Concentrates (EC)

15 parts by weight of the active compounds or active substance mixtures are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The composition has 15% by weight active ingredient content. iv) Emulsions (EW, EO, ES)

25 parts by weight of the active compounds or active substance mixtures are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added by means of an emulsifying machine (eg Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion. The composition has an active ingredient content of 25 wt .-%. v) suspensions (SC, OD, FS)

20 parts by weight of the active compounds or active substance mixtures are comminuted with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the composition is 20% by weight. vi) Water-dispersible and Water-soluble Granules (WG, SG) 50 parts by weight of the active compounds or active substance mixtures are added with the addition of 50

Parts by weight of dispersants and wetting agents finely ground and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The composition has an active substance content of 50% by weight. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active compounds or active substance mixtures are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the composition is 75% by weight. viii) gels (GF)

In a ball mill, 20 parts by weight of the active ingredients or drug mixtures, 10 parts by weight of dispersant, 1 part by weight of swelling agent ("gelling agent") and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content 2. Types of Composition for Direct Application ix) Dusts (DP, DS) 5 parts by weight of the active compounds or active ingredient mixtures are finely ground and weighed 95% by weight. Intimately mixed with finely divided kaolin, thereby obtaining a dust with 5% by weight of active ingredient x) Granules (GR, FG, GG, MG)

0.5 parts by weight of the active compounds or active substance mixtures are finely ground and combined with 99.5 parts by weight of carriers. Common methods are the

Extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content. xi) ULV solutions (UL)

10 parts by weight of the active compounds or drug mixtures are dissolved in 90 parts by weight of an organic solvent z. B. XyIoI solved. This gives a composition for direct application with 10 wt .-% active ingredient content.

The compositions of the mixtures according to the invention generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the compounds I and II. The compounds I and II are in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum) used.

For the treatment of plant propagation materials, in particular seed, usually water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels ( GF). These compositions can be applied to the propagating materials, in particular seeds, undiluted or, preferably, diluted. In this case, the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active compound are present in the compositions to be used for the stain. The application can be done before or during sowing. The treatment of plant propagation material, in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, pelleting, dipping or impregnating the plant propagation material, wherein the treatment preferably takes place by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented.

For seed treatment, suspensions are preferably used. Typically, such compositions contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water ,

The active compounds or active substance mixtures can be used as such or in the form of their compositions, for example in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, brushing , Dipping or pouring. The composition types or forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds or active substance mixtures according to the invention. Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the substances can be dissolved as such or in an oil or solvent, by means of wetting, adhesive, Dispersing or Emulgiermitttel be homogenized in water. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water. The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.

Oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides, and / or other pesticides, if appropriate also immediately before use (tank mix), can be added to the active compounds or active ingredient mixtures or to the compositions containing them. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.

Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example Break Thru S ^240® ; Alcohol alkoxylates, eg. As Atplus 245 ^®, Atplus MBA 1303 ^®, Plurafac LF 300 ^® and Lutensol ON 30 ^®; EO-PO block polymers, eg. B. Pluronic RPE 2035 ^® and Genapol B ^®; Alcohol ethoxylates, eg. As Lutensol XP 80 ^®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ^®.

The invention also encompasses mixtures of component 1 (compounds of the formula I) with one or more further active compounds, eg. As with herbicides, insecticides, growth regulators or with fertilizers, as a pre-mix or possibly only immediately before use (tank mix), these agents can be used alternatively or additionally to the compound II (component 2). When mixing the compound I or the mixture of the compounds I and II or the compositions containing them with one or more further active ingredients, for example, in many cases, the spectrum of action can be broadened or resistance developments can be prevented. In many cases, synergistic effects are obtained. This also applies to the mixture of compound I alone with one or more further active ingredients. The preparation of these compositions for mixtures of active ingredients in a known manner in the form of compositions containing in addition to the active ingredients, a solvent or solid carrier, for. B. in the manner as indicated for compositions of the mixtures of compound I and compound II. With regard to the usual ingredients of such compositions, reference is made to the comments on the compositions containing the compounds I and II. The compositions for mixtures of active compounds are suitable as fungicides for controlling harmful fungi and are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi, as described for the novel mixtures of compounds I and II compounds.

The following list of other active ingredients with which the mixtures according to the invention or their compositions can be used together is intended to illustrate, but not to limit, the possible combinations.

A) growth regulator

Abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat (chlorequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfid , indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), Prohydrojasmon, thidiazoron, tri-penthenol, tributyl phosphorotrithioate, 2,3 5-tri-iodobenzoic acid, trinexapac-ethyl and uniconazole;

B) herbicides

Acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro; Amino acid analogues: bilanafos, glyphosate, glufosinate, sulfosate;

Aryloxyphenoxypropionates: Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl;

Bipyridyls: diquat, paraquat;

Carbamates and thiocarbamates: asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates;

- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;

- Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Triflura- Nn;

Diphenyl ether: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

Hydroxybenzonitriles: bromoxynil, dichlobenil, loxynil;

Imidazolinone: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;

Phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;

- Pyrazines: Chloridazon, Flufenpyr-ethyl, Fluthiacet, Norflurazon, Pyridate;

- pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, pilinoram, picolinafen, thiazopyr;

Sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, fluce- tosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1- ((2-chloro-6-propyl-imidazo [1,2-b] pyridazin-3-yl) sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;

Triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;

Ureas: chlorotoluron, da- muron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;

- other inhibitors of acetolactate synthase: bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam; - Other: Amicarbazone, Aminotriazole, Anilofos, Beflubutamide, Benazoline, Bencarbazone, Benfluresat, Benzofenap, Bentazone, Benzobicyclone, Bromacil, Bromobutide, Bu- tattacil, Butamifos, Cafenstrole, Carfentrazone, Cinidone-Ethlyl, Chlorthal, Cinnamethyl-, Clomazone , Cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanide, fentrazamide, flumigorac-pentyl, flumioxazine, flupoxam, fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, Quinclorac, quinmerac, mesotrione, methylarsenoic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefon, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, Topramezone, 4-hydroxy-3- [2- (2-methoxy-ethoxymethyl) -6-trifluoromethyl-pyridine-3-carbonyl] -bicyclo [3.2.1] oct-3-en-2-one, (3- [ 2-chloro-4-fluoro-5- (3-methyl-2,6-di oxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl) -phenoxy] -pyridin-2-yloxy) -acetic acid ethyl ester, θ-amino-δ-chloro-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-Chloro-3- (2-cyclopropyl-6-methyl-phenoxy) -pyridazin-4-ol, 4-amino-3-chloro-6- (4-chloro-phenyl) -5-fluoro-pyridin-2 carboxylic acid,

4-Amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid methyl ester and 4-amino-3-chloro-6- (4-chloro-3 -dimethylamino-2-fluoro-phenyl) -pyridine-2-carboxylic acid methyl ester; C) Insecticides - Organo (thio) phosphates: Acephate, Azamethiphos, Azinphos-methyl, Chlorpyrifos,

Chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophosphate, methidathion, methyl parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, Phenthoate, Phosalone, Phosmet, Phosphamidone, Phorate, Phoxim, Pirimiphos-Methyl, Profenofos, Prothiofos, Sulprophos, Tetrachlorvinphos, Terbufos, Triazophos, Trichlorfon;

Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, Carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates;

- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalo- thrin, permethrin, prallethrin , Pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,

Insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spinotetramat; Nicotine receptor agonists / antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1- (2-chlorothiazol-5-ylmethyl) -2-nitrimino-3,5-dimethyl- [1, 3,5] triazinane;

GABA antagonists: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1- (2,6-dichloro-4-methylphenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide;

Macrocyclic lactones: Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;

- mitochondrial electron transport chain inhibitor (METI) I acaricides: Fenazaquin, Pyridaben, Tebufenpyrad, Tolfenpyrad, Flufenerim; - METI II and III substances: Acequinocyl, Fluacyprim, Hydramethylnon;

- decoupler: chlorfenapyr;

Inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;

Inhibitors of the sloughing of insects: Cryomazine; Inhibitors of mixed function oxidases: piperonyl butoxide; Sodium channel blocker: indoxacarb, metaflumizone;

- Other: Benclothiaz, Bifenazate, Cartap, Flonicamid, Pyridalyl, Pymetrozine, Sulfur, Thiocyclam, Flubendiamid, Chlorantraniliprole, Cyazypyr (HGW86); Cynopyphron, Flupyrazofos, Cyflumetofen, Amidoflumet, Imicyafos, Bistrifluron and Pyrifluquinazone.

The active ingredients mentioned above as possible alternative or further components, their preparation and their action against harmful fungi are known (see: http: //www.hclrss. Demon.co.uk/index.html; http: //www.alanwood. net / pesticides /); they are commercially available. The compounds named after IUPAC, their preparation and their fungicidal action are also known (see Can. J. Plant Sci 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031; A 226 917; EP-A 243 970; EP-A 256,503; EP-A 428 941; EP-A 532,022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624).

In ternary mixtures, d. H. compositions according to the invention comprising an active substance I and a further active ingredient and a further active ingredient, eg. B. contain two different agents from groups 2.1 to 2.6 or A to C, the weight ratio of compound I to the first further active ingredient depends on the properties of the respective active ingredients, preferably in the range of 1:50 to 50: 1 and in particular in the range from 1:10 to 10: 1. The weight ratio of compound I to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1. The weight ratio of 1. further active ingredient to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1.

Preference is given to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as preferred, and in each case in the respective In accordance with one embodiment of the invention, component 1 in each row of table 2 is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 13, preferably in tables 1 to 7.

Table B

synthesis Examples

1) Synthesis of 1-chloro-2- (4-chloro-2-fluorophenyl) -3- (2-chlorophenyl) propan-2-ol. To a solution of 2-chlorobenzyl chloride (200 μL, 1.7 mmol) in anhydrous diethy Lether (20 ml) was added to magnesium turnings (430 mg, 17.9 mmol) and iodine. The reaction mixture was heated slowly until the iodine color disappeared and the beginning of the reaction indicated by refluxing the solvent. The residual 2-chlorobenzyl chloride (2.0 mL, 15.3 mmol) was added dropwise so that the reaction mixture refluxed. After completion of the addition, stirring was continued for a further 2 h at room temperature and then cooled to 0 ^° C. At this temperature, 4-chloro-2-fluorophenacetyl chloride (3.00 g, 14.5 mmol) in anhydrous toluene (10 mL) was added dropwise. The mixture was then warmed to room temperature and stirred for 3 h. After this time, was again cooled to 0 ⁰ C and treated with a saturated aqueous ammonium chloride solution (10 ml). The organic phase was separated and the aqueous phase extracted with ethyl acetate (2 x 20 ml). The combined organic extracts were dried over sodium sulfate and freed of the solvent. The crude product thus obtained (5.0 g) was used without purification in the next reaction step.

2) Synthesis of (Z) -4-chloro-1- [3-chloro-1- (2-chlorophenyl) prop-1-en-2-yl] -2-fluorobenzene To a solution of 1-chloro-2- (4-chloro-2-fluorophenyl) -3- (2-chlorophenyl) propan-2-ol (5.0 g, ca. 14.5 mmol) in a 1, 4-dioxane / THF mixture (44 ml, 10: 1) At 0 ^° C., first acetic anhydride (1.8 ml, 19.1 mmol) and then concentrated sulfuric acid (100 μl, 1.96 mmol) were added. The reaction mixture was then warmed to room temperature, stirred for 18 h and then cooled to 0 ⁰ C again. At this temperature, saturated saline was added (20 ml). and neutralized with aqueous sodium hydroxide solution (6.2 ml, 50% w / w). The resulting mixture was extracted with ethyl acetate (3x20 ml), the organic phases combined and dried over sodium sulfate. After filtration and removal of the solvent in vacuo, the residue was purified by column chromatography (silica gel, hexane). After combining the appropriate fractions, (Z) -4-chloro-1- [3-chloro-1- (2-chlorophenyl) -prop-1-en-2-yl] -2-fluorobenzene was obtained as a colorless oil (1.40 g , 31% over 2 levels).

¹ H NMR (300 MHz, CDCl ₃ ) δ 8.01 (d, J = 6.9 Hz, 1H), 7.46-7.37 (m, 4H), 7.22-7.10 (m, 2H), 6.8 (s, 1H), 4.50 (s, 2H).

3) Preparation of anti-2- (4-chloro-2-fluorophenyl) -2- (chloromethyl) -3- (2-chlorophenyl) oxirane

To a solution of (Z) -4-chloro-1- [3-chloro-1- (2-chlorophenyl) prop-1-en-2-yl] -2-fluorobenzene (800 mg, 2.53 mmol) in acetic acid ( 20 ml) was added maleic anhydride (2.48 g, 25.3 mmol) and aqueous hydrogen peroxide solution (1.46 ml of a 50% solution, 25.3 mmol). The reaction mixture was stirred for 3 d at 45 ⁰ C, then cooled to room temperature and treated with water (20 ml) and aqueous thiosulfate solution (10% solution, 4 ml). The aqueous phase was extracted with dichloromethane (3x15 ml) and the combined organic phases washed with brine (2x10 ml). The organic phase was dried over sodium sulfate, filtered off and the solvent distilled off. The residue thus obtained was purified by column chromatography (silica gel, 25: 1 hexane / ethyl acetate). This gave anf / -2- (4-chloro-2-fluorophenyl) -2- (chloromethyl) -3- (2-chlorophenyl) oxirane (580 mg, 70%) after combining the appropriate fractions in the form of a colorless solid ,

¹ H NMR (300 MHz, CDCl ₃ ) δ 7.50 (t, J = 9.0 Hz, 1H), 7.49-7.41 (m, 2H), 7.36-7.32 (m, 2H), 7.24-7.14 (m, 2H) , 4.30 (s, 1H), 3.87 (d, J = 12.0 Hz, 1H), 3.37 (d, J = 12.0 Hz, 1H).

4) Preparation of 1 - [(anf /) -2- (4-chloro-2-fluorophenyl) -3- (2-chlorophenyl) oxiran-2-yl) methyl] -1H-1,2,4-triazole

To a solution of anfr-2- (4-chloro-2-fluorophenyl) -2- (chloromethyl) -3- (2-chlorophenyl) oxirane (580 mg, 1.74 mmol) in anhydrous Λ /, Λ / -dimethylformamide (20 ml) at room temperature was added 1, 2,4-triazole (362 mg, 5.24 mmol) and sodium hydride (130 mg, 5.42 mmol). The mixture was stirred first at 60 ^° C. for 20 h and at 75 ^° C. for a further 4 h. It was then cooled to room temperature, diluted with ethyl acetate (20 ml) and washed with brine (3 x 15 ml). The separated organic phase was dried over sodium sulfate, filtered and the solvent distilled off. The residue thus obtained was purified by column chromatography (silica gel, 7: 3 hexane / ethyl acetate). After uniting the to speaking fractions, the title compound (383 mg, 60%) was obtained as a colorless solid.

¹ H NMR (300 MHz, CDCl ₃ ) δ 7.86 (s, 1H), 7.78 (s, 1H), 7.61-7.58 (m, 1H), 7.57-7.37 (m, 3H), 7.23-7.06 ( m, 3H), 4.76 (d, J = 12.0 Hz, 1H), 4.28 (s, 1H), 4.02 (d, J = 12.0 Hz, 1H).

Following this preparation, the following compounds of general formula 1 were prepared as racemates with cis arrangement of triazolylmethyl substituent and ring B of Table 14.

Table 14

Anwendungsbeispiele

applications

The fungicidal activity of the compounds and the mixtures can be demonstrated by the following experiments:

drug treatment

The active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Wettol EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.

Use Example 1 - Efficacy against the scab of apple leaves caused by Venturia inaequalis at 1 day of protective application (Ventin P1)

Leaves of apple plants were sprayed to drip point with aqueous suspension in the drug concentration below. The following day, the treated plants were inoculated with an aqueous spore suspension of Venturia inaequalis. Thereafter, the apple plants were first placed for 24 hours in a water vapor-saturated chamber at 24 ° C and then for 21 days in a greenhouse at temperatures between 20 and 24 ⁰ C. Then the extent of infestation on the top of the leaf was visually determined.

The determined values for the percentage infestation on the leaves were converted into efficiencies% of the untreated control. Efficiency 0 means the same infestation as in the untreated control; Efficiency 100 is 0% infestation. The expected efficiencies for drug combinations were determined according to the Colby formula (Colby, S.R. (Calculating Synergistic and Antagonistic Ac- tions of herbicide Combinations, Weeds, 5, p. 20-22, 1967) and compared with the observed efficiencies.

The efficiency (W) is calculated according to the formula of Abbot as follows:

W = (1-α / β) 100

α corresponds to the fungal infestation of the treated plants in% and β corresponds to the fungal infestation of the untreated (control) plants in%

With an efficiency of 0, the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation. The expected efficiencies for drug combinations were determined according to the Colby formula (Colby, SR (Calculating synergistic and antagonistic responses of herbicide combinations), Weeds, 5, pp 20-22, 1967) and compared with the observed efficiencies.

Colby formula:

E = x + y - x-y / 100

E expected efficiency, expressed as% of untreated control, using the mixture of active substances A and B at concentrations a and bx the efficiency expressed as% of untreated control, when using active substance A at the concentration ay the efficiency, expressed as% of untreated control, when using active substance B in concentration b

Drug preparation for microtiter tests The active ingredients were formulated separately or together as a stock solution with a concentration of 10,000 ppm in DMSO. The active ingredients epoxiconazole, pyraclostobin and trifloxystrobin were used as commercial formulations and diluted with respect to the active ingredient with water.

Calculation method for microtiter tests

The measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs. The determined values for the percentage of relative growth were first averaged, then converted into efficiencies as% of the drug-free control variant. Efficiency 0 is the same growth as in the drug-free control variant, efficiency 100 is 0% growth. The expected efficiencies for drug combinations were determined as above according to the Colby formula and compared with the observed efficiencies.

Use Example 2 - Activity against the causative agent of the late blight Phytophthora infestans in the microtiter test (phytin)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous pea-based zoospore suspension of Phytophthora infestans. The Plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

Combination partner compound 11-1

(used as a mixture of diastereomers trans: cis 68:32)

Use Example 3 - Activity Against the Causeter of the Gray Mold Botrytis cinerea in the Microtiter Test (Botrci)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. Subsequently, a malt-based aqueous spore suspension of Botrytis cinerea was added. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

Use Example 4 - Activity against the causative agent of pyricularia oryzae rice blast in the microtiter test (Pyrior)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. Subsequently, a malt-based aqueous spore suspension of Pyricularia oryzae was added. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

Anwendungsbeispiel 5 - Aktivität gegen den Verursacher des Septoria Blattdürre Septo- ria tritici im Mikrotiter-Test (Septtr)Combination partner compound II-2

Use Example 5 Activity against the causative agent of the Septoria leaf drought Septoria tritici in the microtiter test (Septtr)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous spore suspension based on malt of Septoria tritici. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

From the results of the experiments, it is clear that the mixtures according to the invention are considerably more effective due to the synergism than predicted by the CoI by formula.

Claims

claims 1. Fungicidal mixtures containing as active components 1) Azolylmethyloxirane of the general formula I.

wherein A is phenyl which is substituted by an F and another substituent selected from Cl, C _r C ₄ alkyl, Ci-C ₄ haloalkyl, and C _r C ₄ - alkoxy, B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl or is phenyl which is alkyl substituted by one to three of the following substituents: halogen, NO _2, amino, Ci _-C4 -alkyl, Ci-C ₄ alkoxy, Ci-C ₄ haloalkyl, Ci-C ₄ - haloalkoxy, Ci-C ₄ alkylamino, Ci-C ₄ dialkylamino, thio, or Ci-C ₄ - alkylthio, with the proviso that B is not o-methylphenyl when A is 2-chloro-4-fluorophenyl, as well as their plant-tolerated acid addition or metal salts, and 2) a fungicidal compound II selected from 2.1) strobilurins, selected from Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allylideneaminooxymethyl) -phenyl ) -2-methoxyimino-N-methyl-acetamide; 2.2) Carboxylic acid amides selected from Carboxylic acid anilides: benalaxyl, benalaxyl M, benodanil, bixafen, boscalid, carbowin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxine, penthiopyrad , Tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- (1, 1, 3-trimethyl-indan-4-yl) -nicotinamide, N- (3 ' , 4' Dichloro-5-fluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [2 - (1, 3-dimethyl-butyl) -phenyl] -amide, N- (4'-chloro-3 ', 5-difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole 4-carboxamide, N- (4'-chloro-3 ', 5-difluoro-biphenyl-2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl- 2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 '5-difluoro-4'-methyl-biphenyl-2-yl) -3-trifluoromethyl-1-methyl 1-H-pyrazole-4-carboxylic acid amide, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-2-bicyclopropyl) 2-yl-phenyl) -3-di-fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl- 1 H-pyrazole-4-carboxylic acid amide, N- (2'-fluoro-4'-chloro-5'-methyl-biphenyl- 2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl- 1 H-pyrazole-4-carboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ' , 4 ', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl 1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoro-methylthio) -biphenyl-2-yl) -1-methyl-3-trifluoromethyl- 1 H-pyrazole-4-carboxamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (4 (4-fluoro-3-trifluoromethylphenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl) propoxy) -phenyl) -N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine, N (2 ', 4'-Difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2', 4'-dichlorobiphenyl-2-yl) -3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl -1-methyl- 1 H-pyrazole-4-carboxamide, N- (3 ', 5'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3'-fluorobiphenyl- 2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3'-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide, N- (2'-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2'-chlorobiphenyl-2-yl) -3-difluoromethyl-1 -methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,3,3,3,3-hexafluoropropoxy) -phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide, N- [2- (1,1,2,2-tetrafluoroethoxy) -phenyl] -3- difluoromethyl-i-methyl-1H-pyrazole-4-carboxamide, N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole 4-carboxamide, N- [1,2,3,4-tetrahydro-9- (1-methylethyl) -1, 4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole -4- carboxamide; - Carboxylic acid morpholides: Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide; Other carboxamides: carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide; 2.3) Azoles selected from - Triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, mycelobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazo - Ie, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chlorophenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol; - imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizo- Ie; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole, 1- (4-Chloro-phenyl) -1- (propyn-2-yloxy) -3- (4- (3,4-dimethoxyphenyl) -isoxazol-5-yl) -propan-2-one, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide; 2.4) Nitrogen-containing heterocyclyl compounds selected from Pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 - (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2 , 4-dichloro-nicotinamide; - pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrimine, nitrapyrin, nuarimol, pyrimethanil; - piperazines: triforins; - Pyrroles: fludioxonil, fenpiclonil; - Morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tride- morph; - piperidines: fenpropidine; Dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin; non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octili- none, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester; - Other: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquat-methylsulphate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazid, pyroquilone, quinoxyfen , Triazoxide, tricyclazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5- a] pyrimidine, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1- (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1H-benzoimidazole ,, 6- (3,4-dichlorophenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6- (4-tert-butylphenyl) -5 -methyl- [1,2,4] triazolo [1,5-a] pyiminim-7-ylamine, 5-methyl-6- (3,5,5-trimethyl-hexyl) - [1, 2,4 ] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methyl-6-octyl- [1,2,4] triazolo [1,5-a] pyimidin-7-ylamine, 6-methyl- 5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-yl-amine, 6-ethyl-5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6- (3,5,5-trim ethyl-hexyl) - [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-octyl-5-propyl- [1,2,4] triazolo [1,5-a ] pyrimidin-7-yl-amine, 5-methoxymethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-octyl-5-trifluoromethyl [1, 2 , 4] triazolo [1,5-a] pyrimidin-7-ylamine and 5-trifluoromethyl-6- (3,5,5-trimethyl-hexyl) - [1,2,4] triazolo [1,5-a] pyτimidin-7-ylamine; 2.5) carbamates and dithiocarbamates selected from Thio and dithiocarbamates: Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; - Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester ; 2.6) Other fungicides selected from Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat); - antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A; Nitrophenyl derivatives: Binapacryl, dicloran, dinobutone, dinocap, nitrothal-isopropyl, tecnazene; Organometallic compounds: Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide; Sulfur-containing heterocyclyl compounds: isoprothiolanes, dithianone; Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl; Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phtha-Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitrophenyl) -N- ethyl-4-methyl-benzenesulfonamide; - Inorganic active substances: Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate; - Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (Cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluoro-phenyl) -methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl ) -N-ethyl-N-methylformamidine, N '- (4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (2 -Methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl -propoxy) -phenyl) -N-ethyl-N-methylformamidine, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-y-acyl) -piperidine-1-yl-1-thiazolecarboxylic acid -methyl- (1,2,3,4-tetrahydronaphthalen-1-yl) -amide, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidine 4-yl} -thiazole-4-carboxylic acid-methyl- (R) -1, 2,3,4-tetrahydronaphthalene-1-yl-amide, acetic acid-6-tert-butyl-8-fluoro-2,3- Dimethyl-quinolin-4-yl ester, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester in a synergistically effective amount. 2. Fungicidal mixtures according to claim 1, wherein in the component 1 of the formula IA 2-chloro-4-fluorophenyl, 2-fluoro-4-chlorophenyl, 2-methoxy-4-fluoro-orphenyl, 2-fluoro-4-methoxyphenyl or 2-fluoro-4-methylphenyl. 3. Fungicidal mixtures according to one of claims 1 or 2, wherein in the component 1 of the formula I B is pyridyl, thienyl, thiazolyl, oxazolyl or furyl. 4. A fungicidal mixture as claimed in either of claims 1 or 2, in which in component 1 of the formula IB is phenyl which is substituted by one to three of the following substituents: halogen, NO 2, amino, C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkyl. C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, thio or C 1 -C 4 -alkylthio. 5. Fungicidal mixtures according to claim 4, wherein in the component 1 of the formula 1 B is phenyl which is substituted by one to three of the following substituents halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl or C1-C4-haloalkoxy is substituted. 6. Fungicidal mixtures according to one of claims 1 to 5, containing one of the compounds 1 and one of the compounds 2 in a weight ratio of 100: 1 to 1: 100. 7. Fungicidal mixtures according to one of claims 1 to 6, containing a compound 2 selected from azoxystrobin, kresoxim-methyl, picoxystrobin, pyracoltrobin and trifloxystrobin. 8. Fungicidal mixtures according to one of claims 1 to 6, containing a compound 2 selected from bixafen, carboxin, penthiopyrad, pyrimidinedione, metaxaxyl, N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2- yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide , N- (cis-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-phenyl) -3-difluoromethyl- 1-methyl-1H-pyrazole4-4-carboxamide, N- (2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole 4- carboxamides, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazoles-4-carboxamides, N- (3 ', 4', 5 '-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (2', 4 ', 5'-trifluorobiphenyl-2-yl) -1-methyl-3 -difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole e-4-carboxamides, N- (4'- (trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4 '- (trifluoro-methylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl 1 H-pyrazole-4-carboxamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (4 (4-fluoro-3-trifluoromethylphenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl) propoxy) -phenyl) -N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine , 9. Fungicidal mixtures according to one of claims 1 to 6, containing a compound 2 selected from cyproconazole, difenoconazole, epoxiconazole, flusilazole, flutriafol, myclobutanil, metconazole, propiconazole, prothioconazole, tebuconazole, tetraconazole, prochloraz. 10. Fungicidal mixtures according to one of claims 1 to 6, containing a compound 2 selected from carbendazim, thiabendazole, cyprodinil, fludioxonil, fenpropimorph, captan, fenpropidin, thiram, chlorothalonil, thiophanate methyl, sulfur, copper hydroxide, metrafenone and spiroxamine. 1 1. Fungicidal mixtures according to claim 10, containing a compound 2 selected from carbendazim, fenpropimorph and metrafenones. 12. Use of a fungicidal mixture according to any one of claims 1 to 6 for controlling phytopathogenic fungi. 13. An agrochemical composition containing a solvent or solid carrier and a fungicidal mixture according to any one of claims 1 to 6. 14. Seed containing a fungicidal mixture according to any one of claims 1 to 6. 15. A method for controlling phytopathogenic fungi, characterized in that the fungi, or to be protected against fungal infection, materials, plants, the soil or seeds with an effective amount of a fungicidal Mixture according to one of claims 1 to 6 treated.