WO2010146029A2 - Fungicidal mixtures - Google Patents

Abstract

The invention relates to fungicidal mixtures which comprise 1) azolylmethyloxiranes of general formula (I), wherein the variables are defined as in the application, 2) a fungicidal compound II, and 3) optionally another fungicidal compound II as the active components, the compounds II of components 2 and 3 being independently selected from among the compounds described in the application, with the proviso that components 2 and components 3 are not the same. The invention also relates to the use of the fungicidal mixtures for the control of phytopathogenic fungi and to agents containing said mixtures.

Description

 Fungicidal mixtures

description

The present invention relates to fungicidal compositions comprising as active components

1) Azolylmethyloxirane of the general formula I.

worin die Variablen folgende Bedeutungen aufweisen:

wherein the variables have the following meanings:

B is phenyl which is unsubstituted or substituted by one, two, three or four identical or different substituents L, where L is

L is halogen, cyano, nitro, cyanato (OCN), C -C ₈ -alkyl, C ₈ -HaIo- genalkyl, phenyl-Ci-Cβ-alkyloxy, _C2-C8 alkenyl, _C2-C8 haloalkenyl , _C2-C8 alkynyl, _C2-C8 haloalkynyl, C4-Cio-alkadienyl, C4-Cio-alkadienyl halogen, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy,} d- Cs-alkylsulfonyloxy, _C2-C8 alkenyloxy, _C2-C8 haloalkenyloxy, C2-C ₈ - alkynyloxy, C ₂ -C ₈ haloalkynyloxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -HaIo - gencycloalkyl, _C3-C8 cycloalkenyl, _C3-C8 halocycloalkenyl, C ₃ -C ₈ - cycloalkoxy, C ₃ -C 6 -cycloalkenyloxy, hydroxyimino-Ci-C ₈ alkyl, Ci-Cβ- alkylene, oxy-C2 C4-alkylene, oxy-Ci-C3-alkyleneoxy, C ₈ -Alkoximino-C ₈ - alkyl, C2-C ₈ -Alkenyloximino-C ₈ alkyl, _C2-C8-Ci -Alkinyloximino C ₈ alkyl, S (= O) n A ¹ , C (= O) A ² , C (= S) A ² , NA ³ A ⁴ , phenyl, phenyloxy or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the G group O, N and S; where n, A ¹ , A ² , A ³ , A ⁴ mean:

n is 0, 1 or 2;

A ¹ is hydrogen, hydroxy, Ci-C ₈ alkyl-Al, _{Ci-C8-haloalkyl,} amino, Ci-C ₈ - alkylamino or di-Ci-C ₈ alkylamino, A ^{2 is} one of the groups mentioned at A ¹ or C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -

Haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkynyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 2 -C 8 -alkenyloxy, C 2 -C 8 -haloalkenyloxy, C 2 -C -alkynyloxy, C 2 -C 8 -haloalkynyloxy, _C3-C8 cycloalkyl, C3-C8-

Halocycloalkyl, _C3-C8 cycloalkoxy or _C3-C8-halo cycloalkoxy;

A ^3, A ⁴ are independently hydrogen, Ci-C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl , C ₂ -C ₈ -

Haloalkynyl, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ - cycloalkenyl or C 3 -C ₈ halocycloalkenyl;

where the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups RL:

R ^{L is} halogen, cyano, nitro, _Ci-C8 -alkyl, C ₈ haloalkyl, C ₈ - alkoxy, _{Ci-C8-haloalkoxy, C3-C8} cycloalkyl, C3-C ₈ -Halogencyclo - alkyl, _C3-C8 cycloalkenyl, _C3-C8 cycloalkoxy, C3-C ₈ -Halogencyclo- alkoxy, _{Ci-C8-alkylcarbonyl, Ci-C8-alkylcarbonyloxy,} Ci-C ₈ - alkoxycarbonyl, amino, Ci C ₈ alkylamino, di-C 1 -C ₈ alkylamino;

-S-R, where

R is hydrogen, Ci-C ₈ -alkyl, C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, C ₂ -C ₈ - Haloalkynyl, C (= O) R ³ , C (= S) R ³ , SO ₂ R ⁴ or CN; in which

R ³ represents hydrogen, Ci-C ₈ alkyl-Al, _{Ci-C8-haloalkyl,} Ci-C ₈ alkoxy,

C ¹ -C ₈ haloalkoxy or NA ³ A ⁴ ; and

R ^{4 is} C 1 -C ₈ -alkyl, phenyl-C 1 -C ₈ -alkyl or phenyl, wherein the

Each phenyl group is unsubstituted or substituted with one, two or three groups independently selected from

Halogen and C 1 -C ₄ -alkyl;

wobei B wie oben definiert ist;- a group Dl

where B is as defined above;

- a group Dil QNR ¹

#. ^ S> C R- where # is the point of attachment to the triazolyl ring and Q, R ¹ and R ^{2 are}

Q O or S;

R ^1, R ² independently of one another Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} d-Cs-alkoxy, Ci-Cs-alkoxy-d-Cs-alkoxy, _{Ci-C8-haloalkoxy,} Ci-C ₈ - alkoxy-Ci-Cs-alkyl, Ci -C ₈ alkylthio -alkyl, C ₂ -C ₈ -alkenylthio, C ₂ -C ₈ -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C ₃ -C ₈ cycloalkylthio, phenyl, phenyl-Ci-C ₄ - alkyl, phenoxy, phenylthio, phenyl-Ci-C4-alkoxy or NR ⁵ R ^6, wherein

R ^{5 is} H or C 1 -C ₈ -alkyl and R ^{6 is} C 1 -C ₈ -alkyl, phenyl-C 1 -C ₄ -alkyl or phenyl or R ⁵ and R ⁶ together represent an alkylene chain having four or five C atoms form or form a radical of the formula -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ - or -CH ₂ -CH ₂ -NR ⁷ -CH ₂ -CH ₂ -, in which R ^{7 is} hydrogen or C ₁ -C ₄ - Alkyl means; wherein the aromatic groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three groups selected from halogen and C 1 -C ₄ -alkyl; or

a group SM, where M means:

M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)

Z ² Z ¹ - NZ ³ (E)

in which Z ¹ and Z ^{2 are} independently hydrogen or C ¹ -C 8 -alkyl; Z ³ and Z ^{4 are} independently hydrogen, C ¹ -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;

and their agriculturally acceptable salts, and

2) a compound II, and

3) optionally a further compound II,

wherein the compounds II of components 2 and 3 are independently selected from the following compounds, provided that component 2 and component 3 are not the same:

A) strobilurins:

Azoxystrobin, Dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, 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, Methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarbox-imidoylsulfanylmethyl) -phenyl) acrylate, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl- allylideneaminooxymethyl) -phenyl) -2-methoxy-imino-N-methyl-acetamide;

B) Carboxylic acid amides:

- Carboxylic acid anilides: benalaxyl, benalaxyl M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxylin, Penthiopyrad, Sedaxane, Tecloftalam, Thifluzamide, Tiadinil, 2-Amino

4-methyl-thiazole-5-carboxanilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) nicotinamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'-trifluoromethylthiobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide , N- (2- (1,3-dimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide (penflufen), N- (2- (1 , 3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide;

- Carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;

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

Oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide; C) Azoles:

- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole,

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, triflumizole;

Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole; - Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ;

D) Nitrogen-containing heterocyclyl compounds

Pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethylisoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 (5-Bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloronotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4 -dichlornicotinamid;

Pyrimidines: Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil; - piperazines: triforins;

- Pyrroles: fludioxonil, fenpiclonil;

- morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph;

- piperidines: fenpropidine;

Dicarboximides: fluorimide, iprodione, procymidone, vinclozolin; non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;

- others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoate methyl sulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazide, pyroquilone, quinoxyfen , Triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1 - (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H- benzoimidazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine , 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyimidin-7-ylamine; E) carbamates and dithiocarbamates

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

Carbamates: diethofencarb, benthiavalicalarb, iprovalicarb, propamocarb, propamocarbhydrochloride, valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester; F) Other fungicides Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat);

- Antibiotics: Kasugamycin, Kasugamycin Hydrochloride Hydrate, Polyoxins, Streptomycin, Validamycin A; Nitrophenyl derivatives: binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;

Organometallics: fentin salts such as fentin acetate, fentin chloride, fentin hydroxide;

Sulfur-containing heterocyclyl compounds: dithianone, isoprothiolanes; Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;

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

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

- Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, pyriofenone, 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- (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, 2- {1- [2- (5-methyl-S-trifluoromethyl-pyrazol-1-yl] -acetyl-1-piperidine-1-yl-1-thiazole-2-carboxylate - (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, N-methyl-2- {1 - [2- (2- 5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl) -acet yl] -piperidin-4-yl} -N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide; G) growth regulators abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat (chlormoquat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, Gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), Prohydrojasmon, thidiazuron, tri-penthenol, tributyl phosphorotrithioate, 2, 3,5-tri-iodobenzoic acid, Trinexapac-ethyl and uniconazole; H) 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, cyhalofopbutyl, 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, prosulfocarb, pyributicarb, thiobencarb, triallates;

- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; - Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin;

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

Hydroxybenzonitriles: bromoxynil, dichlobenil, loxynil; Imidazolinones: 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, picloram, picolinafen, thiazopyr;

Sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-propylimidazo [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, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;

- other inhibitors of acetolactate synthase: bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenzpropyl, pyribenzoxime, Pyriftalid, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyroxasulfone, Pyroxsulam;

- Other: Amicarbazone, Aminotriazole, Anilofos, Beflubutamide, Benazoline, Bencarbazon, Benfluresat, Benzofenap, Bentazone, Benzobicyclone, Bromacil, Bromobutide, Butafenacil, Butamifos, Cafenstrole, Carfentrazone, Cinidone-Ethlyl, Chlorthal, Cinmethylin, Clomazone, Cumyluron, Cyprosulfamide, Dicamba , Difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanide, fentrazamide, flumiclorac-pentyl, flumioxazine, flupoxam, fluorochloridone, fluorotamate, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, Methylarsenoic acid, naptalam, oxadiargyl, oxadiazone, oxazirocomefon, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamine, 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-dioxo- 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-pyridine-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; I) insecticides

Organo (thio) phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophos, methidathion, methyl parathion , Mevinphos, monocrotophos,

Oxydemeton-Methyl, Paraoxone, 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, betacyfluthrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, 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,

Diofenolane, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halothane ozid, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;

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,

Spinosad, 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); Cyenopyrafen, Flupyrazofos, Cyflumetofen, Amidoflumet, Imicyafos, Bistrifluron and Pyrifluquinazone, [(3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS) -3- (cyclopropanecarbonyloxy) -6,12-dihydroxy-4,6a, 12b trimethyl-1 1-oxo-9- (pyridin-3-yl) -1, 2,3,4,4a, 5,6,6a, 12a, 12b-decahydro-1 H, 12H-benzo [f] pyrano [4,3-b] chromen-4-yl] methyl cyclopropanecarboxylate,

in a synergistically effective amount.

Furthermore, the invention also relates to compositions in which component 2) is defined as follows:

Biological fungicides, plant strengtheners: Ampelomyces quis- qualis (. Eg the product AQ 10 ^® from Intrachem Bio GmbH & Co. KG Germany,), Aspergillus flavus (. Eg the product AFLAGUARD ^® from Syngenta, Switzerland), Aureobasidium pullulans (eg the product BOTECTOR ^® from. bio-ferm GmbH, Germany), Bacillus pumilus (eg strain NRRL no. B-30087 ^® in SONATA ^®, and BALLAD Plus from. AgraQuest Inc., USA), Bacillus subtilis (eg master NRRL No. B-21661 in Rhapsody ^®, SERENADE ^® MAX and SERENADE ^® ASO of Fa..

AgraQuest Inc., USA), Bacillus subtilis var. Amyloliquefaciens FZB24 (eg the product TAEGRO ^® from. Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (eg the product ASPIRE ^® from. Ecogen Inc., USA), Candida saitoana (eg the products BIOCURE ^® (mixed with lysozyme) and BIOCOAT ^® Micro Flo Company. BotriZen Ltd., Company, USA (BASF SE) and Arysta) chitosan (eg ARMOR ZEN Fa New Zealand), Clonostachys rosea f. catenulata, also called

Gliocladium catenulatum (eg strain J1446. PresTop ^® from Verdera, Finland), Coniothyrium minitans (. Eg the product Contans ^® from Prophyta, Germany), Cryphonectria parasitica (eg the product Endothia parasitica the company CNICM, France), Cryptococcus albidus (eg the product YIELD PLUS ^® from. Anchor bio- Technologies, South Africa), Fusarium oxysporum (. eg the products biofox ^® from Siapa, Italy, and FUSACLEAN ^® from. Natural Plant Protection, France), Metschnikowia fructicola ( eg the product Shemer ^®, Fa.. AgroGreen, Israel), Microdochium dimerum (eg the product ANTI BOT ^® from Agrauxine, France), Phlebiopsis gigantea (eg the product ROTSOP ^® from. Verdera, Finland), Pseudozyma flocculosa (eg the product SPORODEX ^® Plant Products Co. Ltd. Fa., Canada), Pythium oligandrum DV74 (eg the product POLYVERSUM ^® from. Remeslo SSRO, Biopreparaty, Czech Republic), Reynoutria sachlinensis (eg the product REGALIA ^® from Marrone Biol nnovations, USA), Talaromyces flavus V117b (eg the product protus ^® from. Prophyta, Germany), Trichoderma asperellum SKT-1 (eg, the product ECO-HOPE ^® from. Kumiai Chemical Industry Co., Ltd., Japan) T. atroviride LC52 (eg the product SENTINEL ^® from. Agrimm Technologies Ltd, New Zealand), T. harzianum T-22 (eg the product PLANT SHIELD ^® from BioWorks Inc., USA), T. harzianum TH 35 (eg the product ROOT PRO ^® from MyControl Ltd., Israel), T. harzianum T-39 (for example, the products TRICHODEX ^® and TRICHODERMA 2000 ^® from. MyControl Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (eg the product TRICHOPEL the company Agrimm Technologies Ltd, New Zealand), T. harzianum and T. viride ICC012 ICC080 (eg the product remédier ^® WP Fa. Isagro Ricerca, Italy), T. polysporum and T. harzianum (eg product Binab ^® from. Binab Bio-innovation AB, Sweden), T. stromaticum (eg the product TRICOVAB ^® from Ceplac, Brazil), T. virens GL 21 (eg Pro domestic product SOILGARD ^® from Certis LLC, USA), T. viride (eg the products TRIECO ^® from Ecosense Labs. (India) Pvt. Ltd., India and BIO-CURE ^® F from. T. Stanes & Co. Ltd., India), T. viride TV1 (eg the product T. viride TV1 company Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (eg the product BOTRY- ZEN ^® of Botry-Zen Ltd Company, New Zealand); wherein components 1) and 2) are present 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. Furthermore, the invention also relates to seed containing the fungicidal mixtures. Furthermore, the invention also relates to methods for Control of phytopathogenic fungi, characterized in that treating the fungi, or to be protected against fungal attack materials, plants, the soil or seeds with an effective amount of a fungicidal mixture according to the invention. Furthermore, the invention also relates to processes for the preparation of the mixtures according to the invention.

In particular, the invention relates to fungicidal mixtures comprising 1) Azolylmethyloxirane of the general formula I as described above, and 2) a compound II, wherein the compound II of the component 2 is selected from the compounds of groups A to I as described above,

in a synergistically effective amount.

In particular, the invention relates to fungicidal mixtures comprising

1) Azolylmethyloxirane of the general formula I as described above, and

2) a compound II, and

3) a further compound II, wherein the compounds II of components 2 and 3 are independently selected from the compounds of groups A to I as described above, provided that component 2 and component 3 are not the same, in a synergistically effective Amount.

The mixtures comprising at least one compound of the formula I (component 1) and at least one further active compound II (component 2 and optional component 3) are the mixtures according to the invention. The mixtures according to the invention are preferably binary mixtures, particularly preferably ternary mixtures.

Azolylmethyloxiranes of component 1, their preparation and their use in crop protection are known from WO 2009/077471 (PCT / EP2008 / 067483), in which certain mixtures of Azolylmethyloxirane of component 1 are mentioned with other active ingredients. Azolylmethyloxiranes of the general formula I are the compounds I according to the invention.

The active ingredients mentioned above as component 2 and 3, their preparation and their action against harmful fungi are known (cf .: http://www.alanwood.net/pesticides/); they are commercially available. The compounds named after IUPAC, their preparation and their fungicidal action are also (See, Can. J. Plant Sci 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-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 WO 102/41837, WO 99/24187, WO 99/14187, WO 99/24413, WO 99/27783, WO 00/29404, WO 00/46148, WO 00/65913, WO 01/54501, US Pat. 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 widening of the spectrum of action of the known compounds, the present invention mixtures were the object, which show an improved action against harmful fungi, especially for certain indications with reduced total amount of applied drugs.

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 the general formula I and at least one further fungicidal active ingredient (component 2 and optional component 3), eg. B. one or more, for example 1 or 2 active ingredients of the aforementioned groups A to I and optionally one or more agriculturally suitable carriers. It has also been found that, with simultaneous simultaneous or separate application of the compound I and one or more compounds II or when using the compound I and the compound (s) II harmful fungi can be controlled better than with the individual compounds (synergistic mixtures). As mentioned above, these mixtures are of interest in terms of reducing the application rates, since many show an improved action against harmful fungi, especially for certain indications, with a reduced total quantity of applied active substances. By simultaneous joint or separate application of the compound I with one or more compounds II, the fungicidal activity can be increased to a superadditive extent. Common application in the context of this application means that at least one compound I and the at least one other active ingredient II at the same time at the site of action (ie the fungi to be controlled 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 available. This can be achieved by simultaneously applying the compounds I and at least one further active compound II together in a common active substance preparation or in at least two separate active substance preparations or by applying the active ingredients successively to the site of action, wherein the time interval of the individual active substance applications is selected in that the active substance applied at first is present in sufficient quantity at the site of action at the time of application of the other active substance (s). The time sequence of the application of the active ingredients is of minor importance.

In a preferred embodiment, these are binary mixtures, i. H. Compositions according to the invention comprising a compound I and another active ingredient II (component 2), e.g. contain an active ingredient from groups A) to I). Here, the weight ratio of compound I to further active ingredient II depends on the properties of the respective active ingredients, usually in the range from 1: 100 to 100: 1, frequently in the range from 1:50 to 50: 1, preferably in the range from 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. It may also be preferred that the weight ratio is in the range of 1: 2 to 2: 1.

In a further preferred embodiment are ternary mixtures, d. H. compositions according to the invention comprising an active ingredient I and a further active ingredient (component 2) and a second further active ingredient (component 3), for. B. contain two different agents from groups A) to I). Here, the weight ratio of compound I to the first further active ingredient (component 2) depends on the properties of the respective active ingredients, preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1 and in particular in the range from 1:20 to 20: 1. It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1. The weight ratio of compound I to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1:20 to 20: 1 , It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1. The weight ratio of further active ingredient (component 2) to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1. It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1.

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) one or more, also all, contain 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, ie, 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 B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).

In a further embodiment, the user can mix both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups A) to I), 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 containing compounds I and / or active compounds from groups A) to I), together (for example as tank mix) or in succession. The compounds of the formula I can be present in the "thiol" form of the formula Ia or in the "thiono" form of the formula Ib:

wherein D ^* means:

R, wherein R has the meaning defined above;

wobei # die Verknüpfungsstelle mit dem Schwefelatom in Formel Ia bzw. Azolylring in Formel Ib ist und Q, R¹ und R² die oben definierte Bedeutung haben; oder- a group DN ^*

where # is the point of attachment with the sulfur atom in formula Ia or azolyl ring in formula Ib and Q, R ¹ and R ^{2 have} the meaning defined above; or

- a group M, wherein M has the meaning defined above, and wherein the remaining substituents have the meaning defined above.

In particular, the tautomeric forms Ia and Ib are present when D ^{* is} hydrogen.

For the sake of simplicity, only one of the two forms, generally the "thiol" form, is usually listed here in each case.

The compounds I are 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. This also applies to most of the precursors for compounds I described herein, of which the salts and adducts are also subject of the present invention.

Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid. Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms). , Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl which are a 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. As metal ions, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth

Main group, in particular aluminum, tin and lead, as well as the first to eighth subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others into 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.

The compounds 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 compounds of the invention, 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 antimicrobial agents can be used both the uniform diastereomers or enantiomers as well as their resulting in the synthesis of mixtures. The same applies to the fungicides.

The invention therefore relates both to mixtures in which compound I are the pure enantiomers or diastereomers as well as mixtures thereof. This applies to the mixtures according to the invention of the compounds of the formula I. In particular, the scope of the present invention includes the mixtures of the (R) and (S) isomers and the racemates of the compounds I which have chiral centers. Suitable compounds I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.

The compounds of the formula I according to the invention can be prepared in various ways in analogy to known processes of the prior art (see, for example, US Pat in the cited prior art and crop protection news Bayer 57/2004, 2, pages 145-162), or as described in PCT / EP2008 / 067483.

In the definitions of the symbols in the formulas given herein, partial collective terms are used which are generally representative of the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl and the alkyl moieties of composite groups such as

Alkylamino: saturated straight-chain or branched hydrocarbon radicals having from 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C ₆ alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3

Methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above; in particular 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;

Alkenyl and the alkenyl moieties in compounded groups, such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position. In the present invention, it may be preferable to use small alkenyl groups such as (C 2 -C 4) alkenyl, but on the other hand, it may also be preferable to use larger alkenyl groups such as (C 5 -C 8) alkenyl. Examples of alkenyl groups are, for example, C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -Methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2- propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2- Methyl 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl 2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2 Dimethyl 2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2- Dimethyl 3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3- Dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl 3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl ;

Haloalkenyl: alkenyl 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;

Alkadienyl: unsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;

Alkynyl as well as the alkynyl moieties in compounded groups: straight or branched chain hydrocarbon groups of 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-1-butynyl, 1-ethyl-2- butinyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Haloalkynyl: alkynyl, 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;

Cycloalkyl and the cycloalkyl moieties in assembled groups: mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, in particular 3 to 6 carbon ring members, for example Cs-Cβ-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; Halogencycloalkyl: cycloalkyl 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;

Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexene 4- yl and the like;

Halocycloalkenyl: cycloalkenyl 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;

Alkoxy: for an oxygen-bonded alkyl group as defined above, preferably with 1 to 8, more preferably 2 to 6 carbon atoms. Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; as well as e.g. Pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 , 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

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 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, _OCH2 -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; and 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chloro-hexoxy, 6-bromohexoxy, 6-iodo-hexoxy or dodecafluorohexoxy.

Alkylene: divalent linear chains of CH ₂ groups. Preference is given to (C 1 -C 6) -

Alkylene, more preferably (C ₂ -C 4) -alkylene, furthermore it may be preferred (Ci-C ₃ ) - Use alkylene groups. Examples of preferred alkylene radicals are CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ (CH ₂ ) ₂ CH ₂ , CH ₂ (CH ₂ ) ₃ CH ₂ and CH ₂ (CH ₂ ) ₄ CH ₂ ;

A 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S, where the respective heterocycle via a carbon atom or via a nitrogen atom, if contained, may be attached. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen. In particular: three- or four-membered saturated heterocycle (hereinafter also heterocyclyl) containing one or two heteroatoms from the group O, N and S as ring members; A five- or six-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as

Ring members: e.g. monocyclic saturated or partially unsaturated heterocycles containing, in addition to carbon ring members, one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3

Pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4- Thiadiazolidin-3-yl, 1, 2,4-

Thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiazolidin-2-yl, 1, 3,4- Triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- Dihydrothien-2-yl, 2,3-dihydro-thien-3-yl, 2,4-dihydro-2-yl, 2,4-dihydro-3-yl, 2-pyrrolin-2-yl, 2-pyrroline-3 yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-1 5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazole-4 yl, 2,3-

Dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4, 5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazole-4 yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexa hydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropy-imidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3,5-hexahydro-triazin-2-yl and 1,2,4-hexahydro-triazin-3-yl, and the like -ylidene residues; Seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as ring members: for example mono- and bicyclic heterocycles having 7 ring members, containing in addition to carbon ring members one, two or three nitrogen atoms and / or a Oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro [1 H] azepine-1 -, -2-, -3-, -4- , -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepine-2-, -3-, -A-, -5-, -6- or - 7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1, -2-, -3-, -A-, -5-, -6- or -7-yl, 2,3 , 6,7-Tetrahydro [1 H] azepine-1, -2, -3, -A-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, - 3- or ^ 4-yl, tetra-. and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro [1 H] oxepin-2, -3, -4, -5, -6, or -7-yl, 2,3,4,7- Tetrahydro [1H] oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,

2,3,6,7-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3 - or ^ 4-yl, tetra- and hexahydro-1, 3-diazepinyl, tetra- and hexahydro-1, 4-diazepinyl, tetra- and hexahydro-1, 3-oxazepinyl, tetra- and hexahydro-1, 4-oxazepinyl , Tetra- and hexahydro-1, 3-dioxepinyl, tetra- and hexahydro-1, 4-dioxepinyl and the corresponding yliden residues;

5-, 6-, 7-, 8-, 9- or 10-membered aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S: In particular five- or six-membered aromatic mono- or bicyclic heterocycle containing one, two, three or four heteroatoms from the group O, N and S: The respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen. The heterocycle means in particular: -5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present 5-ring heteroaryl groups which may contain, in addition to carbon atoms, one to four nitrogen atoms or one, two or three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg furyl,

Thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, especially 2-furyl , 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4 Pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-

Oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2, 4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazol-3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazol-2-yl;

-6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered ring heteroaryl groups which, in addition to carbon atoms, have one to four or . One, two or three nitrogen atoms may contain as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-

Pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.

In the compounds I (Komponentei the mixtures of the invention), the following meanings of the substituents, in each case alone or in combination, particularly preferred.

According to one embodiment of the invention, B is unsubstituted phenyl.

In another embodiment, B represents phenyl which contains one, two, three or four independently selected substituents L.

According to a further embodiment, the phenyl ring is monosubstituted with a substituent L, wherein L is according to a particular embodiment of this embodiment in the ortho position to the point of attachment of the phenyl ring with the oxirane ring.

In another embodiment, B represents phenyl containing two or three independently selected substituents L.

According to another embodiment of the invention, B is a phenyl ring which contains a substituent L in the ortho position and also has a further independently selected substituent L. In one embodiment, the phenyl ring is 2,3-disubstituted. In another embodiment, the phenyl ring is 2,4-disubstituted. In yet another embodiment, the phenyl ring is 2,5-disubstituted. In yet another embodiment, the phenyl ring is 2,6-disubstituted.

According to another embodiment of the invention, B is a phenyl ring which contains a substituent L in the ortho position and also contains two further independently selected substituents L. In one embodiment, the phenyl ring is 2,3,5-trisubstituted. In another embodiment, the phenyl ring is 2,3,4-tri- substituted. In yet another embodiment, the phenyl ring is 2,4,5-trisubstituted.

L independently has the meanings given above for L. If it is not otherwise stated, L is preferably independently selected from halogen, cyano, nitro, cyanato (OCN), Ci _-C4 -alkyl, Ci-C ₄ haloalkyl, _{Ci-C4-alkoxy, Ci-C4-} Haloalkoxy, Cs-Ce-cycloalkyl, C ₃ -C ₆ -halocycloalkyl, SA ¹ , C (= O) A ² , C (= S) A ² , NA ³ A ⁴ ,; where A ¹ , A ² , A ³ , A ⁴ mean:

A ¹ is hydrogen, hydroxy, Ci-C ₄ -alkyl, _{Ci-C4-haloalkyl;}

A ^{2 is} one of the groups mentioned at A ¹ or C ¹ -C ₄ -alkoxy, C ¹ -C ₄ -

Haloalkoxy, C ₃ -C 6 -cycloalkyl, Cs-Cβ-halocycloalkyl, C ₃ -Cβ -cycloalkoxy or C ₃ -C 6 -halocycloalkoxy;

A ³ , A ⁴ independently of one another are hydrogen, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl;

wherein the aliphatic and / or alicyclic groups of

Remaining definitions of L can in turn carry one, two, three or four identical or different groups RL:

R ^{L is} halogen, cyano, nitro, Ci-C alkyl ₄ -alkyl, Ci-C ₄ haloalkyl, Ci-C ₄ - alkoxy, _{Ci-C4-haloalkoxy, C3-C6-cycloalkyl,} Cs-Cβ-halocycloalkyl, Amino, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino.

Furthermore preferably, L is independently selected from halogen, NO2, amino -C ₄ - alkyl, Ci-C ₄ alkoxy, _{Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino,} d-C ₄ - Dialkylamino, thio and Ci-C ₄ alkylthio.

Furthermore preferably, L is independently selected from halogen, Ci-C ₄ alkyl, -C ₄ - haloalkyl, _{Ci-C4-alkoxy, Ci-C4} haloalkoxy, and _{Ci-C4-haloalkylthio.}

According to a further preferred embodiment, L is independently selected from F, Cl, Br, CH _3, C ₂ H _5, iC ₃ H _7, tC ₄ H _9, OCH _3, OC ₂ H _5, CF _3, CCl _3, CHF ₂ , CCIF ₂ , OCF ₃ , OCHF ₂ and SCF ₃ , in particular selected from F, Cl, CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , CF ₃ , CHF ₂ , OCF ₃ , OCHF ₂ and SCF ₃ , According to one embodiment, L is independently selected from F, Cl, CH _3, OCH _3, CF _3, OCF ₃ and OCHF. ₂ It may be preferred that L is independently F or Cl.

In a further embodiment, the substituent B is phenyl which is substituted by one, two or three halogen atoms. In another embodiment, B is phenyl which is unsubstituted or substituted by one, two or three substituents independently selected from halogen, NO ₂ , amino, C 1 -C ₄ alkyl, C 1 -C ₄ alkoxy, C 1 -C _{4 4} haloalkyl, Ci-C ₄ - haloalkoxy, Ci-C ₄ alkylamino, Ci-C ₄ dialkylamino, thio, and Ci-C ₄ alkylthio.

In a further embodiment of the invention, B is not ortho-methylphenyl.

The meanings of the variables B and L for compounds I described above apply correspondingly to the precursors of the compounds according to the invention.

According to one embodiment of the invention, D is a group SR, where R is hydrogen (compounds I-SH). According to a further embodiment, D is a group SR, where R is C 1 -C ₄ -alkyl, in particular methyl or ethyl, preferably methyl.

According to a further embodiment of the invention, D is a group SR, where RC (= O) R ³ and R ^{3 is} NA ³ A ⁴ , where A ³ and A ⁴ independently of one another are hydrogen or C ¹ -C 8 -alkyl.

According to a further embodiment of the invention, D is a group SR, where R is C (= O) R ³ and R ³ is hydrogen, Ci _-C4 -alkyl, Ci-C ₄ haloalkyl, Ci-C ₄ - alkoxy, , Ci-C ₄ haloalkoxy, phenyl or benzyl. In a specific embodiment thereof, R ^{3 is} hydrogen. According to a further embodiment thereof, R ^{3 is} C 1 -C ₄ -alkyl, in particular methyl or ethyl, preferably methyl. According to yet another embodiment, R ^{3 is} C 1 -C ₄ -haloalkyl, in particular trifluoromethyl. According to yet another embodiment, R ^{3 is} C 1 -C ₄ -alkoxy, in particular methoxy or ethoxy.

According to another embodiment of the invention, D is a group SR, where R is C (= O) R ³ and R ^{3 is} (C 1 -C ₄ ) alkylamino, di (C 1 -C ₄ ) alkylamino or

Phenylamino means. In one embodiment thereof, R ^{3 is} methylamine, dimethylamino, ethylamino, diethylamino or phenylamino.

According to another embodiment of the invention, D is a group SR, where R is CN.

According to a further embodiment of the invention, D is a group SR, where R is SO ₂ R ⁴ and R ^{4 is} C 1 -C ₄ -alkyl, phenyl-C 1 -C ₄ -alkyl or phenyl, where the phenyl groups are each unsubstituted or are substituted by one, two or three groups independently selected from halogen and C 1 -C ₄ -alkyl. According to another embodiment of the invention, D is a group SM, wherein M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E )

Z ²

Z ¹ - NZ ³ (E), wherein

Z ¹ and Z ^{2 are} independently hydrogen or C 1 -C ₄ -alkyl; and Z ³ and Z ^{4 are} independently hydrogen, Ci-C ₄ -AlkVl, benzyl or phenyl. According to one embodiment, M represents Na, ½Cu, 3Fe, HN (CH ₃ ) S, HN (C ₂ H ₅ ) S, N (CHs) ₄ or H ₂ N (C ₃ HT) ₂ , in particular Na, 1/2 Cu, HN (CHs) ₃ or HN (C ₂ Hs) ₃ , especially Na, 1/2 Cu, HN (CHs) ₃ or HN (C ₂ Hs) ₃ .

According to a further embodiment of the invention, the invention relates to mixtures of the compounds of the formula I in which the variables have the following meanings: B is phenyl which is substituted in the ortho position by a further substituent L, where L is

L is fluorine, chlorine, bromine, Ci -C ₈ -alkyl, C ₈ alkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -

Cycloalkoxy, C 1 -C ₈ -alkylcarbonyloxy, C (= O) A ² , where A ² is

A ² is hydrogen, hydroxy, Ci-C ₈ -alkyl, C ₈ haloalkyl, amino, _{d-C8-alkylamino} or di-Ci-C ₈ alkylamino, Ci-C ₈ alkoxy;

D -S-R, where

R is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C (OO) R 3, C (= S) R 3, SO ₂ R 4, or CN; in which

R3 is hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-

Haloalkoxy or NA3A4; and

R 4 is C 1 -C 8 -alkyl, phenyl-C 1 -C 8 -alkyl or phenyl, wherein the

Each phenyl group is unsubstituted or substituted with one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;

wobei B wie oben definiert ist;- a group Dl

where B is as defined above;

- a group Dil QNR ¹

#. ^ S> C R- where # is the point of attachment to the triazolyl ring and Q, R ¹ and R ^{2 are}

Q O or S;

R ^1, R ² independently of one another Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} d-Cs-alkoxy, Ci-Cs-alkoxy-d-Cs-alkoxy, _{Ci-C8-haloalkoxy,} Ci-C ₈ - alkoxy-Ci-C ₈ alkyl, C -C alkylthio ₈ -alkyl, C ₂ -C ₈ -alkenylthio, C ₂ -C ₈ -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C ₃ -C ₈ cycloalkylthio , phenyl, phenyl-Ci-C ₄ - alkyl, phenoxy, phenylthio, phenyl-Ci-C4-alkoxy or NR ⁵ R ^6, wherein

R ^{5 is} H or C 1 -C ₈ -alkyl and R ^{6 is} C 1 -C ₈ -alkyl, phenyl-C 1 -C ₄ -alkyl or phenyl or R ⁵ and R ⁶ together represent an alkylene chain having four or five C atoms form or form a radical of the formula -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ - or -CH ₂ -CH ₂ -NR ⁷ -CH ₂ -CH ₂ -, in which R ^{7 is} hydrogen or C ₁ -C ₄ - Alkyl means; wherein the aromatic groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three groups selected from halogen and C 1 -C ₄ -alkyl; or

a group SM, where M means:

M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)

Z ² Z ¹ - NZ ³ (E)

in which Z ¹ and Z ^{2 are} independently hydrogen or C ¹ -C 8 -alkyl; Z ³ and Z ^{4 are} independently hydrogen, C 1 -C 6 -alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;

and their agriculturally acceptable salts.

According to a further embodiment of the invention, the invention relates to mixtures of the compounds of the formula I in which the variables have the following meanings:

B is phenyl substituted in ortho position with another substituent L, wherein L is: L is fluoro, chloro, bromo, methyl;

D -S-R, where

R is hydrogen, C 1 -C 8 alkyl, C (= O) R 3, or CN; wherein R3 is C1-C8 alkyl;

- SO ₂ R ₄ , where

R 4 is C 1 -C 8 alkyl;

- a group Dl

wobei B wie oben definiert ist; oder

where B is as defined above; or

a group SM, where M means:

M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)

Z ²

Z ¹ - NZ ³ (E)

wherein Z ¹ and Z ^{2 are} independently hydrogen or Ci-Cs-alkyl; Z ³ and Z ^{4 are} independently hydrogen, C 1 -C 6 -alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;

and their agriculturally acceptable salts.

In another embodiment of the invention, D in the compounds of formula I is --SO ₂ R ₄ , wherein R ₄ and B are as defined herein.

According to a further embodiment of the invention, D is a group D1 (compounds 1-dimer), where B is independently defined as defined herein or preferably:

Vorzugsweise haben beide B in den Verbindungen l-dimer die gleiche Bedeutung.l-dimer

Preferably, both B in the compounds l-dimer have the same meaning.

According to another embodiment of the invention, D is a group Dil, where # is the point of attachment to the triazolyl ring and Q, R ¹ and R ^{2 are} as defined herein or preferably defined:

Particular preference is given to mixtures of the compounds of the formula I (component 1) in which the variables have the following meanings: B is phenyl which is substituted by a substituent L, where L is halogen or C 1 -C 8 -alkyl:

Particular preference is given to mixtures of the compounds of the formula I (component 1) in which the variables have the following meanings: B 2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl.

Particular preference is given to mixtures of the compounds of the formula I (component 1) in which the variables have the following meanings: D - SR, where

R is hydrogen, C ₁ -C ⁶ -alkyl, C (= O) R ³ , SO ₂ R ⁴ or CN; wherein R ³ is d-Cβ-alkyl, Ci-C ₈ -alkoxy, R ⁴ d-Cβ-alkyl.

Particular preference is given to mixtures of the compounds of the formula I (component

1), in which the variables have the following meanings:

B is phenyl which is substituted by a substituent L, where L is

L is halogen, C 1 -C ₈ -alkyl, C 1 -C -haloalkyl. D - SR, where

R is hydrogen, C ₁ -C ⁶ -alkyl, C (= O) R ³ , SO ₂ R ⁴ or CN; wherein R ³ is d-Cβ-alkyl, Ci-C ₈ -alkoxy, R ⁴ d-Cβ-alkyl.

The most preferred compounds of formula I are the following

Compounds 1-1 to 1-10, wherein in each case in particular enantiomer pairs or enantiomers with trans arrangement of ring A and ring B are preferred: 1-1 2- [trans-3- (2-chlorophenyl) -2- (3-fluorophenyl ) -oxiranylmethyl] -2,4-dihydro

[1,2,4] triazole-3-thione I-2 2- [trans-2- (3-fluorophenyl) -3- (2-fluorophenyl) -oxiranylmethyl] -2,4-dihydro-

[1, 2,4] triazole-3-thione

I-3 2- [trans- (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -2,4-dihydro- [1,2,4] triazole-3-thione I-4 1 - [trans-2 - (3-fluorophenyl) -3- (2-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1H-

[1,2,4] triazole I-5 1- [trans-2- (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -5-methylsulfanyl-1 H-

[1, 2,4] triazole I-6 1 - [trans-3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1 H-

[1, 2,4] triazole

1-7 [trans-3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methanesulfonyl-1 H- [1,2,4] triazole

I-8 thiocarbonic acid S- {2- [3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H-

[1, 2,4] triazol-3-yl) methyl ester I-9 1 - [trans-3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-thiocyanato-1 H-

[1, 2,4] triazole 1-10 thioacetic acid S- {2- [trans-3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H- [1,2,4] triazole 3-yl} ester

Alternative spelling of the trans-enantiomer pairs:

1-1 2- [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2,4-dihydro-

[1,2,4] triazole-3-thione I-2 2- [rel (2R, 3S) -2- (3-fluorophenyl) -3- (2-fluorophenyl) -oxiranylmethyl] -2,4-dihydro-

[1,2,4] triazole-3-thione I-3 2- [rel (2R, 3S) - (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -2,4-dihydro- [1, 2 , 4] triazol-

3-thione

I-4 1 - [rel (2R, 3S) -2- (3-fluorophenyl) -3- (2-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1 H- [1,2,4] triazole

I-5 1 - [rel (2R, 3S) -2- (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -5-methylsulfanyl-1H-

[1, 2,4] triazole I-6 1 - [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1 H- [1, 2,4] triazole I-7 [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methanesulfonyl-1 H- [1,2,4] triazole 1-8 thiocarbonic acid S- {2-rel (2R, 3S) - [3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H- [1,2,4] triazol-3-yl ester methyl ester I-9 1 - [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-thiocyanato

1 H- [1,2,4] triazole -10-thioacetic acid S- {2- [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H- [1 , 2,4] triazol-3-yl} ester

The components 2 and 3 are preferably selected independently of one another as described in the following compositions:

Preference is given to compositions of a compound I (component 1) with at least one active ingredient from group A) (component 2 and / or 3) of the strobilurins and especially selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin , According to a specific embodiment of the invention Preferred compositions comprising a compound I (component 1), in particular a compound selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10, and as component 2 comprise an active ingredient from the group A) of strobilurins, wherein component 2 is in particular selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. According to a specific embodiment, these are binary mixtures which contain only the two components as active ingredients. According to a further embodiment, these mixtures comprise a further component (component 3) selected from the group B) of the carboxamides, in particular selected from bixafen,

Boscalid, fluopyram, isopyrazam, penthiopyrad, sedaxanes, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide and penflufen.

Also preferred are compositions of a compound I (component 1) with at least one active compound selected from the group B) (component 2 and / or 3) of the carboxamides and especially selected from bixafen, boscalid, isopyrazam,

Fluopyram, penflufen, penthiopyrad, sedaxane, fenhexamid, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamide), zoxamide, carpropamide, mandipropamide and N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) - 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from group C) (component 2 and / or 3) of the azoles and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil .

Penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, benomyl, carbendazim and ethaboxam. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, 1-8 , 1-9 and 1-10.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from group D) (component 2 and / or 3) of the nitrogen-containing heterocyclyl compounds and especially selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, Fodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin,

Famoxadone, fenamidone, probenazole, proquinazide, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine , According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10. Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from group E) (component 2 and / or 3) of the carbamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalicarb, benthiavalicarb and propamocarb. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from the fungicides of group F) (component 2 and / or 3) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl aluminum, H3PO3 and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and N-methyl-2- {1 - [(5-methyl-3-trifluoromethyl-1H -pyrazol-1-yl) -acetyl] -piperidin-4-yl} -N - [(1 R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to one embodiment, the compositions according to the invention comprise a compound I (component 1), and a component 2, wherein the component 2 is a G) growth regulator. In particular, component 2 is selected from chlormequat (chlorequat chloride), mepiquat (mepiquat chloride), metconazole, paclobutrazole, prohexadione (prohexadione-calcium), trinexapac-ethyl and uniconazole. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, 1-8 , 1-9 and 1-10.

According to a further embodiment, the compositions according to the invention comprise a compound I (component 1), and a component 2, wherein the component 2 is an insecticide selected from group I). According to a preferred embodiment, these are binary mixtures comprising as active ingredients a component 1) and a component 2) which is selected from group I). According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to one embodiment, the insecticide of component 2) is selected from the group of organo (thio) phosphates, in particular selected from acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl parathion, monocrotophos, phorates, profenofos and terbufos. According to a specific embodiment of the invention, the compound is I

(Component 1) each selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, 1-9 and 1-10. According to a further embodiment, the insecticide of component 2) is selected from the group of carbamates, in particular selected from aldicarb, carbaryl, carbofuran, carbosulfan, methomyl and thiodicarb. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is selected from the group of pyrethroids, in particular selected from: bifenthrin, cyfluthrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, lambda-cyhalothrin and tefluthrin. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is selected from the group of inhibitors of insect growth, in particular selected from lufenuron and spirotetramat. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is selected from the group of nicotine receptor agonists / antagonists, in particular selected from: clothianidin, imidacloprid, thiamethoxam and thiacloprid. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is selected from the group of GABA antagonists, in particular selected from: endosulfan and fipronil. According to a particular embodiment of the invention, the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-

3, I-4, I-5, I-6, I-7, I-8, I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is selected from the group of macrocyclic lactones, in particular selected from: abamectin, emamectin, spinosad and spinetoram. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to yet another embodiment, the insecticide of component 2) is hydramethylnone. According to a specific embodiment of the invention, the

Compound I (component 1) in each case selected from the compounds 1-1, I-2, I-3, I-

4, I-5, I-6, I-7, I-8, I-9 and 1-10. According to yet another embodiment, the insecticide of component 2) is fenbutatin oxide. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

In yet another embodiment, the insecticide of component 2) is selected from chlorfenapyr, cyazypyr (HGW86), cyflumetofen, flonicamid, flubendiamide, indoxacarb and metaflumizone. According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to a further embodiment, these are ternary mixtures which, in addition to the components mentioned, comprise a component 3) which is selected from the above-mentioned active compounds II of group I). According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

According to a further embodiment, these are ternary mixtures which, in addition to the two components mentioned, comprise a component 3) which is selected from the active compounds II of groups A) to G). According to a specific embodiment of the invention, the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.

The active ingredients II of group I) and their pesticidal activity and processes for their preparation are known (see also http://www.hclrss.demon.co.uk/index.html). For example, commercially available drugs can be found in The Pesticide Manual, 14th Edition, British Crop Protection Council (2006), and other publications. Compound BB) of group I)

mit dem lUPAC-Namen [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropanecarbonyloxy)-6,12-dihydroxy- 4,6a, 12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1 ,2,3,4,4a,5,6,6a, 12a, 12b-decahydro- 1 11-1,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropancarboxylat sowie ihre Pestizide Wirkung ist in WO2006/129714 und WO2009/081851 offenbart. Besonders bevorzugte Komponenten 2 sind Verbindungen II, die ausgewählt sind aus der Gruppe der folgenden Verbindungen:

with the IUPAC name [(3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS) -3- (cyclopropanecarbonyloxy) -6,12-dihydroxy-4,6a, 12b-trimethyl-11-oxo-9- (Pyridin-3-yl) -1, 2,3,4,4a, 5,6,6a, 12a, 12b-decahydro-1 11-1, 12H-benzo [f] pyrano [4,3-b] chromen 4-yl] methyl cyclopropanecarboxylate and its pesticidal activity is disclosed in WO2006 / 129714 and WO2009 / 081851. Particularly preferred components 2 are compounds II which are selected from the group of the following compounds:

11-1 epoxiconazole

II-2 metconazole

II-3 tebuconazole

II-4 fluquinconazole

II-5 flutriafol

II-6 triticonazole

II-7 prothioconazole

II-8 kresoxim-methyl

II-9 Pyraclostrobin

11-10 Orysastrobin

11-1 1 dimethomorph

11-12 5-Ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidines-7-ylamines

11-13 pyrimethanil

11-14 metalaxyl

11-15 fenpropimorph

11-16 Dodemorph

11-17 iprodione

11-18 Mancozeb

11-19 Metiram

II-20 thiophanate-methyl

11-21 chlorothalonil

II-22 Metrafenone

II-23 Bixafen

II-24 Boscalid

II-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide

II-26 Sedaxane

II-27 isopyrazam

II-28 fluopyram

II-29 Penflufen

Particularly preferred mixtures are the binary mixtures of Table B, wherein each line corresponds to one embodiment of the mixtures according to the invention. Table B: Binary mixtures comprising a component 1 selected from compounds of the formula I and a component 2 selected from the groups A to

According to a further embodiment of the invention, the active compounds II as component 2) are the following:

II-30 Cyflufenamid

11-31 spiroxamine

II-32 fenpropidin

II-33 Proquinazide

II-34 dimoxystrobin

II-35 Iprovalicarb 11-36 cyprodinil

11-37 folpet

11-38 fludioxonil

11-39 zoxamide

11-40 fluazinam

11-41 cyazofamide

II-42 Benthiavalicarb

II-43 fluopicolide

II-44 Ethaboxam

II-45 Amisulbrom

According to yet another embodiment of the invention, the active compounds II as component 2) are the following:

II-46 Prochloraz II-47 Dithianone

II-48 difenoconazole

According to yet another embodiment of the invention, the active compounds II as component 2) are the following: II-49 azoxystrobin

II-50 Trifloxystrobin

II-56 picoxystrobin

II-57 Fluoxastrobin

According to yet another embodiment of the invention, the active substance as component 2) is the following

11-51 Penthiopyrad

Further preferred components 2 are compounds II which are selected from the group of growth regulators G), in particular selected from the following compounds:

II-52 mepiquat chloride

II-53 Chloroquatloride II-54 Trinexapac-ethyl

II-55 Prohexadione-Calcium.

According to a further embodiment, particularly preferred components 2 are compounds II, which are selected from group I), in particular selected from the following compounds: 11-1 a Acephat II-2a Chlorpyrifos ll-3a dimethoate ll-4a methamidophos ll-5a terbufos ll-6a aldicarb ll-7a carbofuran ll-8a bifenthrin ll-9a alpha-cypermethrin

M-IOa deltamethrin

11-11 a Lambda-cyhalothrin II-12a Betacyfluthrin II-13a Zetacypermethrin II-14a Esfenvalerate II-15a Pirimicarb II-16a Tefluthrin II-17a Spirotetramat II-18a Endosulfan II-19a Abamectin II-20a Spinosadll-21 a Spinetoram II 22a hydramethylnon ll-23a fenbutatin oxide ll-24a chlorfenapyr ll-25a cyazypyr ll-26a cyflumetofen ll-27a flubendiamide ll-28a indoxacarb ll-29a metaflumizone ll-30a fipronil ll-31 a [(3S, 4R, 4aR, 6S, 6aS , 12R, 12aS, 12bS) -3- (cyclopropanecarbonyloxy) -

6,12-dihydroxy-4,6a, 12b-trimethyl-1 1-oxo-9- (pyridin-3-yl) -

1, 2,3,4,4a, 5,6,6a, 12a, 12b-decahydro-1 H, 12H-benzo [f] pyrano [4,3-b] chromen-4-yl] methyl cyclopropanecarboxylate.

According to a further embodiment, particularly preferred components are 2

Compounds II selected from the group of the following compounds: II-32a Clothianidin II-33a Dinotefuran II-34a Imidacloprid II-35a Thiamethoxam II-36a Nitenpyram II-37a Acetamiprid II-38a Thiacloprid According to a further embodiment, particularly preferred components 2 are compounds II which are selected from the active ingredients of group H). In particular, the active compounds according to this embodiment are selected from the group of the following compounds of group H): 11-1 b glyphosate II-2b imazamox

Particularly preferred components 3 are compounds II which are selected from the group of the following compounds:

11-1 epoxiconazole

II-2 metconazole

11- 3 tebuconazole

II-6 triticonazole II-7 prothioconazole

II-8 kresoxim-methyl

II-9 Pyraclostrobin

11-1 1 dimethomorph

11-12 5-Ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidines-7-ylamine 11-13 pyrimethanil

11-14 metalaxyl

11-15 fenpropimorph

11-18 Mancozeb

11-19 Metiram II-20 thiophanate-methyl

11-21 chlorothalonil

II-22 Metrafenone

II-23 Bixafen

II-24 Boscalid II-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide

II-26 Sedaxane

II-27 isopyrazam

II-28 Fluopyram II-29 Penflufen

provided that component 2 and component 3 are not the same.

Particularly preferred mixtures are the ternary mixtures of Table T, each line corresponding to one embodiment of the mixtures according to the invention. Table T: Ternary mixtures comprising a component 1 selected from compounds of the formula I, one component 2 selected from the groups A to and one component 3 selected from the groups A to I.

According to a further embodiment, preference is given to mixtures which comprise a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of compounds 11-1 to II-29, Il 34, II-46 to 11-51, II-56 and II-57 (see above), and component 3 is a compound II selected from the compounds

II-34 Dimoxystrobin II-46 Prochloraz

II-47 Dithianon

II-48 difenoconazole

II-49 Azoxystrobin

II-50 trifloxystrobin 11-51 penthiopyrad

II-56 picoxystrobin

II-57 fluoxastrobin provided that component 2 and component 3 are not the same. According to yet another embodiment, preference is given to those mixtures which comprise a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of compounds 11 -1 to II-29, II-46 to II-48, II-49 to 11-51 and II-52 to II-55 (see above) and component 3 is a compound II which is selected from the compounds II- 52 mepiquat chloride

II-53 Chlormequat chloride

II-54 Trinexapac-ethyl

II-55 prohexadione calcium of group G), provided that component 2 and component 3 are not the same. According to yet another embodiment, preference is given to those mixtures comprising a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of the following compounds :

II-8 kresoxim-methyl

II-9 Pyraclostrobin

II-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole

4-carboxamide

II-26 Sedaxane

II-28 fluopyram

II-29 Penflufen

II-49 Azoxystrobin

II-50 Trifloxystrobin

11-51 Penthiopyrad

and wherein the component 3 is a compound II selected from the group of the following compounds: II-30a fipronil II-32a clothianidin II-34a imidacloprid II-35a thiamethoxam

According to yet another embodiment, preference is given to those mixtures comprising a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of the following compounds : ll-32a clothianidin II-34a imidacloprid II-35a thiamethoxam, and component 3 fipronil (compound ll-30a).

According to a further embodiment, preference is given to those ternary mixtures which comprise a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of the following compounds : II-8 Kresoxim-methyl

II-9 Pyraclostrobin

II-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide

II-26 Sedaxane

II-28 fluopyram 11-29 Penflufen

11-49 azoxystrobin

11-50 trifloxystrobin

11-51 is penthiopyrad and component 3 is fipronil (Compound ll-30a).

The mixtures of compounds I and II (= mixtures according to the invention) I or the compositions thereof (= compositions according to the invention) are suitable as fungicides for controlling harmful fungi. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, which in particular originate from the classes of the Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytriomycetes, 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 according to the invention and the compositions of the invention for combating a variety of pathogenic fungi on various crops 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, lettuce, 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; Sweet herb (Stevia rebaudania); 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 or compositions of the invention for controlling 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. Cucumbers,

Tomatoes, beans and pumpkins and on the propagation material, eg. B. 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, onions, rhizomes, shoots and others

Plant parts, including seedlings and young plants, 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 inventive

Mixtures or Compositions Compositions are used to control a variety of fungal pathogens in cereal crops, e.g. 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 way 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 are mentioned, which by breeding and genetic engineering measures a tolerance against certain herbicide classes, such as auxin herbicides such. B. Dicamba or 2,4-D, bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors, acetolactate synthase (ALS) -I inhibitors such. As sulfonylureas, Enolpyruvylshikimat-3-Phosphate synthase (EPSPS) inhibitors such. As glyphosate, glutamine synthetase (GS) - inhibitors such. As glufosinate, lipid biosynthesis inhibitors such. Acetyl-CoA carboxylase (ACCase) inhibitors, or oxynil herbicides (eg, bromoxynil or loxynil). Furthermore, crops were produced that are resistant to several herbicide classes by several genetic engineering measures, for example, resistant to glyphosate and glufosinate, or against glyphosate and a herbicide of another class such. ALS inhibitors, HPPD inhibitors, auxin herbicides and ACCase inhibitors. These herbicide resistance technologies are e.g. As described in Pest Managers. Be. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references cited therein. By Breeding and mutagenesis was z. B. Clearfield ^® rapeseed (BASF SE, Germany) produced, the tolerance to imidazolinones, z. B. imazamox, has, or Express- ^® sunflowers (DuPont, USA), the tolerance to sulfonylurea herbicides such. Tribenuron. 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 names Roundup Ready ^® (glyphosate-resistant, Monsanto, USA) Cultivance ^® (imidazolinone -resistent, BASF SE, Germany) and Liberty link ^® (glufosinate-resistant, Bayer CropScience, Germany) are available sind.Weiterhin also includes plants using genetic engineering measures with one or more toxins, for. 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. B. from streptomycetes; 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. Many of the aforementioned toxins confer on the plants that produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera and butterflies (Lepidoptera) and nematodes (Nematoda). Genetically engineered plants that produce one or more genes encoding insecticidal toxins, e.g. B. in the above-mentioned

Publications described and partly commercially available, such as. As YieldGard ^® (Corn varieties that produce the toxin CrylAb), YieldGard ^® Plus (corn varieties that produce the CrylAb and Cry3Bb1 toxins), Starlink ^® (maize varieties that produce the Cry9c toxin), Herculex ^® RW (maize varieties that contain the toxins Cry34Ab1, Cry35Ab1 and produce 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); VIPCOT ^® (cotton varieties that produce a VIP toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt-Xtra ^®, NatureGard® ^®, KnockOut ^®, BiteGard ^®, Protecta ^®, Bt1 1 (z. B. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing 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, Belgium (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 0 392 225), resistance proteins (eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (z B. Potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of 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.

The mixtures according to the invention or

Compositions for controlling 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: Botryotinia fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including salad, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (cereal); 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 (e.g., BC zeae-maydis), rice, sugar beets (e.g., BC beticola), sugar cane, vegetables, coffee, soybeans (e.g., BC sojina, or C. kikuchii) and rice; Cladosporium spp. on tomato (eg BC fulvum:

Velvet spot disease) and cereals, e.g. B. C. herbarum (wheat spike) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (eg C. carbonum), cereals (eg C. sativus, anamorph: B. sorokiniana: brown spot) and rice (eg C. miyabeanus, anamorph: H. oryzae); Colletotrichum (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. B. C. sasakii (leaf sheath sting) on rice; Corynespora cassiicola (leaf spot) on soybeans and ornamental plants; Cycloconium spp., Z. B. C. 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. B. D. phaseolorum (stalk disease)

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: burning 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, Anamorph: 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 pigeon or whitish sprout) 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 phaseolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Microdochium (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), bulbous plants (for example BP destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust)

soybeans; Phialophora 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., z. BP viticola (vine peronospora, downy 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. To cereals such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases conferred thereby; Pseudocercosporella herpotrichoides (culm shift, 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; Pseudopezicula 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, P. kuehnii to sugar cane and z. BP asparagi on asparagus (eg BP asparagi); Pyrenophora (anamorph: Drechslera) tritici- repentis (leaf drought) on wheat or P. teres (net stains) on barley; Pyricularia spp., E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and cereals; 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 collocygni (speckle disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes,

Lawn, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants, eg. R. solani (root / stem rot) on soybeans, R. solani (leaf-sheath spirit) on rice or R. cerealis (acute 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) on vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotiorum) and soybeans (eg S. rolfsii); Septoria spp. on different plants, eg. S. glycines (leaf spot) on soybeans, S. tritici (Septoria leaf drought) on wheat and S. (Syn. Stagonospora) nodorum (leaf and spice tan) on cereals; Uncinula (Syn. Erysiphe) necator (powdery mildew, anamorphic: Oidium tuckeri) on grapevine; Setospaeria spp. (Leaf spot) on corn (e.g., S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (Dust fires) on maize, (eg S. reiliana: flaming spirit), millet and sugar cane; 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) to tobacco, pome fruit, Vegetable crops, soybeans and cotton, e.g. 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) 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. (Firefighting) on cereals (for example BU nuda and U. avaenae), maize (for example, maydis: corn buckthorn brandy) and sugarcane; Venturia spp. (Scab) on apples (eg BV inaequalis) and pears; and Verticillium spp. (Deciduous and cloudy) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and

Cultivated crops, such as. B. V. dahliae on strawberries, rape, potatoes and tomatoes.

The mixtures or compositions according to the invention are also suitable for controlling harmful fungi in the storage protection (also of crops) and in the protection of materials and buildings. The term "material and building protection" covers the protection of technical and non-living materials such. As adhesives, glues, wood, paper and cardboard, textiles, leather, color dispersions, plastics, coolants, fibers and tissues, against the infestation and destruction by unwanted microorganisms such as fungi and bacteria. In wood and material 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 compounds of the formula I, and also those of the formula II, can be present in various crystal modifications whose biological activity may be different. Their mixtures are included in the scope of the present invention.

The mixtures or compositions according to the invention are suitable for increasing plant health. Moreover, the invention relates to a method for enhancing plant health by treating the plants, the plant propagating material and / or the place where the plants are to grow or grow with an effective amount of the compounds I or the compositions according to the invention.

The term "plant health" includes those conditions of a plant and / or its crop which are determined by various 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 mixtures according to the invention are used as such or in the form of a

Composition applied by the harmful fungi, their habitat or to be protected against fungal attack plants, plant propagating materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the mixture according to the invention. The application can be both before and after the infection of plants, plant

Propagating materials, eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.

Plant propagating materials may be used prophylactically together with or already before sowing or together with or even before transplanting with the mixtures according to the invention as such or with a composition of them (composition containing at least one compound I and at least one compound II, preferably one or two compounds II).

In addition, the invention relates to agrochemical compositions containing a solvent or solid carrier and the mixture according to the invention and their use for controlling harmful fungi.

The term "agent" is often used in this context to mean the term "composition", in particular "agrochemical composition", and "formulation".

An agrochemical composition contains a fungicidally effective amount of the mixture according to the invention. The expression "effective amount" means an amount of the agrochemical composition or mixture according to the invention 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 vary widely and are influenced by numerous factors, such as the harmful fungus to be controlled, the particular crop or material being treated, climatic conditions and compounds.

The compounds I and the one or more compounds II can be applied simultaneously, jointly or separately or successively, the

Sequence with separate application in general has no effect on the control success. The method of controlling harmful fungi is by the separate or combined application of the compound I and the compound (s) II or the mixtures of the compound I and the compound (s) II by spraying or dusting the seeds, the plants or the soil or after sowing the plants or before or after emergence of the plants. The compounds I and II may 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 compounds I and the compounds II and their N-oxides and salts or mixtures thereof 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 purpose; It should in any case ensure a fine and uniform distribution of the compounds of the mixtures according to the invention.

Examples of composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which may be either soluble or dispersible in water or gels for the treatment of plant propagating materials such as seeds (GF).

In general, the composition types (eg EC, SC, OD, FS, WG, SG, WP, SP, SS, WS, GF) are used diluted. Composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.

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, eg paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, 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 strongly polar solvents, eg amines such as N-methylpyrrolidone , considering. In principle, solvent mixtures and mixtures of the abovementioned solvents and water can also be used.

Solid carriers are mineral soils 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, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

As surfactants (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ^® grades, Borregaard, Norway), phenol, naphthalene (Morwet ^® types, Akzo Nobel, USA) and dibutyl (nekal ^® types, BASF, Germany), and of fatty acids, alkyl and alkylarylsulfonates, 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, polyoxyethyleneoctylphenol 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 methylcellulose), h ydrophob modified starches, polyvinyl alcohol (Mowiol ^® types, Clariant, Switzerland), polycarboxylates (Sokalan ^® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin ^® types, BASF, Germany), polyethylenimine (Lupasol ^® types, BASF , Germany), polyvinylpyrrolidone and their copolymers into consideration.

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 sheet 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 diclorophene and

Benzyl alcohol (Proxel ^®. Fa. ICI or Acticide ^® RS from Thor Chemie and Kathon ^® MK from. Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide ^® MBS from 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 under the names rhodamine B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1, Pigment blue 15: 4,

Pigment blue 15: 3, Pigment blue 15: 2, Pigment blue 15: 1, Pigment blue 80, Pigment yellow 1, Pigment yellow 13, Pigment red 48: 2, Pigment red 48: 1, Pigment red 57: 1, Pigment red 53: 1, 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 well-known dyes and pigments.

Examples of adhesives are polyvinylpyrrolidone, 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 can be prepared by mixing or jointly grinding the compounds I and the further active compounds II with at least one solid carrier. Granules, for. As coated, impregnated and homogeneous granules can be prepared by binding the active ingredients 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 cornmeal, tree bark, wood and nut shell meal, 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 ingredients 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 ingredients 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 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 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 ingredients are comminuted with the addition of 10 parts by weight of dispersants 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 are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and are removed by means of technical equipment (for example 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 ingredient content of 50% by weight. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. 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, 10 parts by weight Dispersing agent, 1 part by weight of swelling agent ("gelling agent") and 70 parts by weight of water or of an organic solvent to a fine suspension .. Dilution with water results in a stable suspension with 20 wt .-% active ingredient content Types of composition for direct application ix) dusts (DP, DS)

5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content. x) Granules (GR, FG, GG, MG)

0.5 part by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are 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 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 from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I and II or mixtures thereof. The compounds I and II are preferably used in a purity of 90% to 100%, preferably 95% to 100% (NMR spectrum). 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. Here, the corresponding

2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active ingredient 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.

Usually, 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 compounds I and II or their mixtures can be used as such or in the form of their compositions, for. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, coating, dipping or pouring. The composition types 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 (wettable powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. 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 successfully used in the ultra-low-volume (ULV) process, whereby it is possible to apply compositions containing more than 95% by weight of active ingredient or even the active ingredient without additives.

The application rates in the application in crop protection, depending on the nature of the desired effect between 0.001 and 2.0 kg of active ingredient 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. In the treatment of plant propagation materials, eg. B. state, are generally drug amounts (or drug mixing amounts) of 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, in particular 5 bis 100 g / 100 kg used. When used in material or storage protection, the application rate of active ingredient or 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 active substances or active substance mixtures or the compositions containing them may contain oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides and / or pesticides, if necessary, also be added immediately before use (tank mix). 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. As adjuvants in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S ^240® ; Alcohol alkoxylates, eg. B. 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. B. Lutensol ^® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ^® RA. synthesis Examples

The synthesis of the compounds of the formula I is carried out as described below (and in WO 2009/077471 (PCT / EP2008 / 067483)).

The instructions given in the following synthesis examples were, with appropriate modification of the starting compounds to obtain further

Compounds of formula I or the precursors thereof used.

Melting points were obtained on a Mel-Temp II instrument and are uncorrected.

1 H-NMR spectra were measured on a Bruker AC 300 spectrometer at 300 MHz and are based on tetramethylsilane as internal standard (referred to

Aldrich or Cambridge Isotope Laboratories).

ESI mass spectra were taken on a Shimadzu LCMS-2010 EV

Mass spectrometer measured. APCI mass spectra were recorded on a Shimadzu

LCMS-2010 EV mass spectrometer measured.

HPLC analyzes were performed using an Alltech Alltima C18 Rocket column, with PDA detection at 254 nm, on a Shimadzu Prominence HPLC system unless otherwise specified. At a flow rate of 2.5 mL per minute, the following schedule was used:

Example 1-1 Synthesis of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole 5 (4H) -thione

To a solution of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole (5.0 g , 15.3 mmol) in dry tetrahydrofuran (THF, 80 mL) at -78 ⁰ C was added dropwise lithium diisopropylamide (LDA, 10.0 mL, 19.9 mmol, 2.0 M in THF). After 30 minutes, sulfur (980 mg, 30.6 mmol) was added. The reaction mixture was stirred for 18 hours, being allowed to warm to -78 ⁰ C 18 ⁰ C. The reaction mixture was added with saturated ammonium chloride solution (30 ml) and then extracted with ethyl acetate (50 ml). The organic phase was washed with saturated sodium chloride solution (40 ml_ three times), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 3: 2 hexane / ethyl acetate), recrystallized with hexane / methylene chloride and purified by column chromatography (silica gel, 3: 2 hexane / ethyl acetate). The target compound (2.1 g, 38%) was obtained as a white solid.

1 H NMR (300 MHz, CDCl 3) δ 7.90 (s, 1H), 7.63-7.19 (m, 7H), 7.04-6.92 (m, 1H), 5.05 (d, 1H), 4.11 (s, 1 H), 3.73 (d, 1 H).

Example I-2 Synthesis of 1- [rel- (2S, 3R) -3- (2-fluorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole 5 (4H) -thione

To a solution of 1- [rel- (2S, 3R) -3- (2-fluorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1 H -1, 2,4-triazole (1.0 g , 3.2 mmol) in dry tetrahydrofuran (THF, 20 mL) at -78 ⁰ C dropwise n-butyllithium (2.4 mL, 3.8 mmol, 1.6 M in hexane) was added. After 20 minutes, sulfur (200 mg, 6.4 mmol) was added. The reaction mixture was stirred at -78 ⁰ C for 5 hours. The reaction mixture was added with methanol (10 mL) and saturated ammonium chloride solution (30 mL) and then extracted with ethyl acetate (50 mL). The organic phase was washed with saturated sodium chloride solution (three times 40 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 4: 1 methylene chloride / ethyl acetate). The objective compound (155 mg, 14%) was obtained as a white solid (mp 125- 130 ⁰ C).

Example I-3 Synthesis of 1- [rel- (2S, 3R) -2- (3-fluorophenyl) -3-o-tolyloxiran-2-ylmethyl] -1 H -1, 2,4-triazole-5 (4H ) -thione

To a solution of 1- [rel- (2S, 3R) -2- (3-fluorophenyl) -3-o-tolyloxiran-2-ylmethyl] -1H-1,2,4-triazole (408 mg, 1.32 mmol ) in dry tetrahydrofuran (THF, 10 mL) was added at -78 ⁰ C was added dropwise lithium diisopropylamide (LDA, 0.86 mL, 1.72 mmol, 2.0 M in THF). After 20 minutes, sulfur (82 mg, 2.6 mmol) was added. The reaction mixture was stirred for 4 hours, starting at -70 ⁰ C and slowly brought to room temperature overnight. The reaction mixture was added with saturated ammonium chloride solution (30 mL) and then extracted with ethyl acetate (50 mL). The organic phase was washed with saturated sodium chloride solution (three times 40 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by recrystallization from hexane / methylene chloride. The target compound (110 mg, 25%) was obtained as a yellow solid. 1 H NMR (300 MHz, CDCl 3) δ 7.68 (s, 1H), 7.49 (m, 1H), 7.33-7.15 (m, 6H), 7.00-6.89 (m, 1H), 5.10 (d, 1 H), 4.02 (s, 1H), 3.74 (d, 1H), 2.39 (s, 3H).

Example I-4 Synthesis of 1- [rel- (2S, 3R) -3- (2-fluorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -5- (methylthio) -1H-1, 2,4-triazole

To a solution of 1- [rel- (2S, 3R) -3- (2-fluorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole (300 mg , 0.96 mmol) in dry tetrahydrofuran (THF, 10 ml_) was added (0.72 ml at -78 ⁰ C was added dropwise n-butyl lithium, 1.16 mmol, added 1.6 M in hexane). After 20 minutes, dimethyl disulfide (86 μl_, 0.96 mmol) was added and the solution was stirred at -78 ⁰ C for 30 minutes. The reaction mixture was added with methanol (10 mL) and saturated ammonium chloride solution (15 mL) and then extracted with ethyl acetate (20 mL). The organic phase was washed with saturated sodium chloride solution (three times 20 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 13: 2 methylene chloride /

Ethyl acetate). The target compound (140 mg, 41%) was obtained as a white solid (mp 89-92 ° C).

Example I-5 Synthesis of 1-rel - [(2S, 3R) -2- (3-fluorophenyl) -3-o-tolyloxiran-2-ylmethyl] -5- (methylthio) -1H-1, 2,4 triazole

To a solution of 1- [rel- (2S, 3R) -2- (3-fluorophenyl) -3-o-tolyloxiran-2-ylmethyl] -1H-1,2,4-triazole (192 mg, 0.61 mmol ) in dry tetrahydrofuran (THF, 8 mL) was added at -78 ⁰ C was added dropwise lithium diisopropylamide (LDA, 0:40 mL, 0.80 mmol, 2.0 M in THF). After 15 minutes, dimethyl disulfide (83 uL, 0.92 mmol) was added and the solution was stirred at -78 ⁰ C for 4 hours. The reaction mixture was added with saturated ammonium chloride solution (15 mL) and then extracted with ethyl acetate (20 mL). The organic phase was washed with saturated sodium chloride solution (three times 20 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 3: 1 to 1: 1 hexane / ethyl acetate). The target compound (120 mg, 55%) as a yellow solid was obtained.

1 H NMR (300 MHz, CDCl3) δ.72 (s, 1H), 7.60-7.50 (m, 1H), 7.31-6.91 (m, 7H), 4.51 (d, 1H), 4.08 (s, 1H), 3.94 (d, 1H), 2.48 (s, 3H), 2.41 (s, 3H).

Example I-6 Synthesis of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -5- (methylthio) -1H-1, 2,4-triazole

150 mg of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H-1,2,4-triazole were dissolved in 5 ml of THF dissolved and treated at room temperature with 7 mg of sodium hydride. The mixture was stirred briefly and then 35 mg of methyl iodide were added. The mixture was stirred at room temperature overnight, water was added and extracted several times with ethyl acetate. The organic phase was with Washed water, dried and concentrated. The crude product was purified by column chromatography with cyclohexane / ethyl acetate. This gave 67 mg of the desired product (70%, melting point 98 ° C).

Example 1-7 Synthesis of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -5- (methylsulfonyl) -1H-1, 2,4-triazole

A mixture of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -5- (methylthio) -1H-1, 2,4 Triazole (352 mg, 0.94 mmol) and m-CPBA (632 mg, 2.81 mmol) in CH 2 Cl 2 (8 mL) were stirred at room temperature for 20 hours. The reaction mixture was washed with 1N sodium hydroxide solution (twice per 20 ml_) and saturated sodium chloride solution (twice per 20 ml), dried with sodium sulfate and freed of the solvent. The residue was purified by column chromatography (silica gel, 5: 1 hexane / ethyl acetate). The target compound (315 mg, 82%) was obtained as a white solid. 1 H NMR (300 MHz, CDCl 3) 5 7.89 (s, 1H), 7.59-7.14 (m, 7H), 7.06-6.94 (m, 1H), 5.30 (d, 1H), 4.31 (d, 1 H), 4.20 (s, 1 H), 3.1 1 (s, 3H).

Example I-8 Synthesis of thiocarbonic acid {2- [Rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) -oxiranylmethyl] -2H- [1,2,4] triazole-3 -yl} ester methyl ester 150 mg 1 - [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H - 1, 2,4- Triazole-5 (4H) -thione was dissolved in 5 ml of THF and treated at room temperature with 7 mg of sodium hydride. The mixture was stirred briefly and then 24 mg of methyl chloroformate were added. The mixture was stirred at room temperature overnight, water was added and extracted several times with ethyl acetate. The organic phase was washed with water, dried and concentrated. The crude product was purified by column chromatography with cyclohexane / ethyl acetate. This gave 50 mg of the desired product (51%). HPLC-MS: 3.682 min (m / z: 420)

Example I-9 Synthesis of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -5-thiocyanato-1H-1, 2, 4-triazole

A mixture of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole-5 (4H ) -thione (200 mg, 0.6 mmol), triethylamine (152 μL, 1.1 mmol) and bromine cyanide BrCN (88 mg, 0.8 mmol) in dry tetrahydrofuran (THF, 10 mL) was stirred at room temperature for 2 h. It was

Ethyl acetate (20 mL) was added and washed with saturated sodium chloride solution (three times 20 mL each), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 10: 1 hexane / ethyl acetate). The target compound (120 mg, 56%) was obtained as a white solid. 1 H NMR (300 MHz, CDCl 3) δ 7.82 (s, 1H), 7.59-7.00 (m, 8H), 4.88 (d, 1H), 4.21 (s, 1H), 4.12 (d, 1H) , Example 1-10 Synthesis of S-1 - [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H-1, 2,4 triazol-5-yl ethane thioate

To a mixture of 1- [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H -1, 2,4-triazole-5 ( 4H) -thione (1 10 mg, 0:30 mmol) and Trieethylamin (83 μl_, 0.60 mmol) in dry tetrahydrofuran (THF, 5 ml) at 0 ⁰ C was added dropwise acetyl chloride (32 μl_ optionally 0:45 mmol) and maintained at this temperature for 2 Stirred for hours. The target compound (130 mg, 100%) was obtained as a brown oil. 1 H NMR (300 MHz, CDCl 3) δ 8.29 (s, 1H), 7.66-7.20 (m, 7H), 7.04-6.90 (m, 1H), 5.21 (d, 1H), 4.11 (s, 1 H), 3.72 (d, 1 H), 2.89 (s, 3H).

Analogously to Example 1-10, the compound 1-11 can be prepared starting from the corresponding starting materials:

Example 1-11 Synthesis of S-1 - [rel- (2S, 3R) -3- (2-fluorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H-1, 2,4 triazol-5-yl ethane thioate

applications

The fungicidal action of the mixtures according to the invention can be demonstrated by the following experiments:

microtest

drug treatment

The active ingredients were formulated separately or together as stock solution with a concentration of 10,000 ppm in DMSO.

The active ingredient Orysastrobin was used as a commercial formulation and diluted with respect to the active ingredient with water!

The determined values (measured parameters) for the percentage infestation on the leaves were compared with the growth of the active ingredient-free control variant and the fungus-free and active ingredient-free blank value in order to determine the relative growth in% of the

Pathogens in the individual active ingredients were determined and were thus in efficiencies

% of the untreated control converted. Efficiency 0 means the same infestation as in the untreated control; Efficiency 100 is 0% infestation. The expected efficiencies for drug combinations were according to the Colby formula (Colby, S.R.

(Calculating synergistic and antagonistic responses of herbicidal combinations, Weeds,

15, 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 efficacies for drug combinations were determined according to the Colby formula (Colby, S.R. (Calculating synergistic and antagonistic responses of herbicide combinations), Weeds, 15, 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

Use Example 1 - 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.

Binary mixtures

Ternäre Mischungen

Ternary mixtures

Application Example No. 2 - Activity against the cause 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 steam-saturated chamber at temperatures of 18 ° C established. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

Binary mixtures

Ternary mixtures

Application Example No. 3 - Activity against the causative agent of rice blast Pyricularia oryzae 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.

Binary mixtures

Application Example No. 4 - 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.

Binary mixtures

Ternäre Mischungen

Ternary mixtures

The results of the experiments show that the mixtures according to the invention are considerably more effective due to the synergism than predicted according to the Colby formula.

Claims

claims 1. Fungicidal mixtures comprising as active components 1) Azolylmethyloxiranes of I

wherein the variables have the following meanings: B is phenyl which is unsubstituted or substituted by one, two, three or four identical or different substituents L, where L is L is halogen, cyano, nitro, cyanato (OCN), C -C ₈ -alkyl, C ₈ -HaIo- genalkyl, phenyl-Ci-Cβ-alkyloxy, _C2-C8 alkenyl, _C2-C8 haloalkenyl , _C2-C8 alkynyl, _C2-C8 haloalkynyl, C4-Cio-alkadienyl, C4-Cio-alkadienyl halogen, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy,} d- Cs-alkylsulfonyloxy, _C2-C8 alkenyloxy, _C2-C8 haloalkenyloxy, C2-C ₈ - alkynyloxy, _C2-C8 haloalkynyloxy, _C3-C8 cycloalkyl, Cs-C ₈ -HaIo- gencycloalkyl, _C3-C8 cycloalkenyl, _C3-C8 halocycloalkenyl, Cs-C ₈ - cycloalkoxy, Cs-Cβ-cycloalkenyloxy, hydroxyimino-C ₈ alkyl, Ci-Cβ- , Oxy-C2-C4-alkylene is alkylene, oxy-Ci-C3-alkyleneoxy, C ₈ -Alkoximino-C ₈ - alkyl, C2-C ₈ -Alkenyloximino-C ₈ alkyl, C2-C ₈ -Alkinyloximino-Ci-C ₈ -alkyl, S (= O) _n A ¹ , C (= O) A ² , C (= S) A ² , NA ³ A ⁴ , phenyl, phenyloxy or a five- or six- membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S; where n, A ¹ , A ² , A ³ , A ⁴ mean: n is 0, 1 or 2; A ¹ is hydrogen, hydroxy, Ci-C ₈ -alkyl, C ₈ haloalkyl, amino, Ci-C ₈ - Alkylamino or di-C 1 -C ₈ -alkylamino, A ^{2 is} one of the groups mentioned at A ¹ or C 2 -C ₈ -alkenyl, C 2 -C ₈ - Haloalkenyl, _C2-C8 alkynyl, _{C2-C8-haloalkynyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, C2-C8} alkenyloxy, _C2-C8 haloalkenyloxy, C 2 -C ₈ -alkynyloxy, C 2 -C ₈ -haloalkynyloxy, C 3 -C ₈ -cycloalkyl, C 3 -C ₈ -halocycloalkyl, C 3 -C ₈ -cycloalkoxy or C 3 -C ₈ -halocycloalkoxy; A ^3, A ⁴ are independently hydrogen, Ci-C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl , C ₂ -C ₈ - haloalkynyl, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ - cycloalkenyl or C 3 -C ₈ halocycloalkenyl; where the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R ^L : R ^{L is} halogen, cyano, nitro, _Ci-C8 -alkyl, C ₈ haloalkyl, C ₈ - alkoxy, _{Ci-C8-haloalkoxy, C3-C8} cycloalkyl, C3-C ₈ -Halogencyclo - alkyl, _C3-C8 cycloalkenyl, _C3-C8 cycloalkoxy, C3-C ₈ -Halogencyclo- alkoxy, _{Ci-C8-alkylcarbonyl, Ci-C8-alkylcarbonyloxy,} Ci-C ₈ - alkoxycarbonyl, amino, Ci C ₈ alkylamino, di-C 1 -C ₈ alkylamino; -S-R, where R is hydrogen, Ci-C ₈ -alkyl, C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, C ₂ -C ₈ - Haloalkynyl, C (= O) R ³ , C (= S) R ³ , SO ₂ R ⁴ or CN; in which R ³ represents hydrogen, Ci-C, _C-C8 haloalkyl, _{Ci-C8-alkoxy,} Ci-C is ₈ -haloalkoxy or NA ³ A ⁴ ₈ -alkyl; and R ^{4 is} C 1 -C ₈ -alkyl, phenyl-C 1 -C ₈ -alkyl or phenyl, wherein each of the phenyl groups is unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C ₄ -alkyl; - one

where B is as defined above; - a group Dil QNR ¹ #. ^ S> C R- where # is the point of attachment to the triazolyl ring and Q, R ¹ and R ^{2 are} Q O or S; R ^1, R ² independently of one another Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} d-Cs-alkoxy, _{Ci-C8-alkoxy-Ci-C 8} alkoxy, _{Ci-C8-haloalkoxy,} Ci- C ₈ - Alkoxy-Ci-C ₈ alkyl, Ci _-C8-Al alkylthio, C ₂ -C ₈ -alkenylthio, C ₂ -C ₈ -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C ₃ -C ₈ cycloalkylthio, phenyl, phenyl-Ci-C ₄ - alkyl, phenoxy, phenylthio, phenyl-Ci-C4-alkoxy or NR ⁵ R ^6, wherein R ⁵ is H or Ci-C ₈ alkyl and R ⁶ is C ₈ alkyl , Phenyl-C 1 -C ₄ -alkyl or phenyl or R ⁵ and R ⁶ together represent an alkylene chain having four or five C atoms or a radical of the formula -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ - or -CH ₂ -CH ₂ -NR ⁷ -CH ₂ -CH ₂ - form, wherein R ^{7 is} hydrogen or Ci-C ₄ alkyl; wherein the aromatic groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three Groups selected from halogen and C 1 -C ₄ -alkyl; or a group SM, where M means: M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E) Z ² Z ¹ - NZ ³ (E) in which Z ¹ and Z ^{2 are} independently hydrogen or C 1 -C ₈ -alkyl; Z ³ and Z ^{4 are} independently hydrogen, C 1 -C ₈ alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C ₄ alkyl; and their agriculturally acceptable salts, and 2) a compound II, and 3) optionally a further compound II, wherein the compounds II of components 2 and 3 are independently selected from the following compounds, provided that component 2 and component 3 are not the same: A) strobilurins: Azoxystrobin, Dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, 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- methyl acrylate, methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarbox-imidoylsulfanylmethyl) -phenyl) acrylate, 2- (2- (3- (2,6-dichlorophenyl) -1- methyl-allylideneaminooxymethyl) -phenyl) -2-methoxy-imino-N-methyl-acetamide; B) Carboxylic acid amides: - carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, Penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methylthiazole-5-carboxanilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) nicotinamide, N- ( 3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'-trifluoromethylthiobiphenyl-2-yl) -3-difluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide, N- (2- (1,3-dimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4 carboxamide (Penflufen), N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide; - Carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph; 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; C) Azoles: - Triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, 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, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole; - Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ; D) Nitrogen-containing heterocyclyl compounds 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-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 - (5-Bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloronotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4 -dichlornicotinamid; Pyrimidines: Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil; - piperazines: triforins; - Pyrroles: fludioxonil, fenpiclonil; - morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; - piperidines: fenpropidine; Dicarboximides: fluorimide, iprodione, procymidone, vinclozolin; non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, 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, difenzoquatmethylsulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazid, pyroquilon, qui - Noxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1 - (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H-benzoimidazole, 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a ] pyrimidine, 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; E) carbamates and dithiocarbamates - 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; F) Other fungicides Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat); - antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A; Nitrophenyl derivatives: binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene; Organometallics: fentin salts such as fentin acetate, fentin chloride, fentin hydroxide; Sulfur-containing heterocyclyl compounds: dithianone, isoprothiolanes; Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, Hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide; - Inorganic active substances: Phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; - Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, pyriofenone, 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-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N' - (4- (4 Fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethyl-silanyl-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-yl-acetyl-1-piperidine-1-yl-thiazo-m-carboxylic acid-methyl] (1,2,3,4-tetrahydronaphthalen-1-yl) -amide, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl } -thiazole-4-carboxylic acid-methyl- (R) -1, 2,3,4-tetrahydronaphthalen-1-yl-amide, acetic acid-6-tert-butyl-8-fluoro-2,3-dimethyl-quinoline 4-yl-ester, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-ester, N-methyl-2- {1- [2- (5 -methyl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidine 4-yl} - N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide; G) 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; H) 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, Trifluralin; 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, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-propylimidazo [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-pyrimidine 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-chlorophenyl) -5-fluoropyridine-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 carboxylsäuremethylester; I) 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, phorates, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorinophos, terbufos, triazophos, trichlorfon; Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates; Pyrethroids: allethrin, betacyfluthrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenorhrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, Lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silica fluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin, insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas Chlorfluazuron, 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-methyl-phenyl) -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); Cynopyphers, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron and pyrifluquinazone, [(3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS) -3- (cyclopropanecarbonyloxy) -6,12-dihydroxy-4 , 6a, 12b-trimethyl-1 1-oxo-9- (pyridin-3-yl) -1, 2,3,4,4a, 5,6,6a, 12a, 12b-decahydro-1 1 H, 12H- benzo [f] pyrano [4,3-b] chromen-4-yl] methyl cyclopropane decarboxylate, in a synergistically effective amount. 2. Fungicidal mixtures according to claim 1, comprising 1) Azolylmethyloxirane of the general formula I as described in claim 1, and 2) a compound II, and 3) another compound II, wherein the compounds II of components 2 and 3 are independently selected from the compounds of groups A to I as described in claim 1, provided that component 2 and component 3 are not the same, in a synergistically effective amount. 3. Fungicidal mixtures according to one of claims 1 to 2, wherein in the component 1 of the formula I B is phenyl which contains exactly one substituent L in or- tho position to the point of attachment of the phenyl ring with the oxirane ring. 4. Fungicidal mixtures according to one of claims 1 to 3, wherein in the component 1 of the formula ID is - SR, wherein R is hydrogen, C 1 -C 6 -alkyl, C (= O) R ³ , SO ₂ R ⁴ or CN ; where R ³ is C 1 -C 6 -alkyl, C 1 -C ₈ -alkoxy, R ⁴ is C 1 -C 6 -alkyl. 5. Fungicidal mixtures according to one of claims 1 to 4, wherein the component 1 is selected from the following compounds: 1-1 2- [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) -oxiranylmethyl] -2,4-dihydro [1,2,4] triazole-3-thione I-2 2- [rel (2R, 3S) -2- (3-fluorophenyl) -3- (2-fluorophenyl) -oxiranylmethyl] -2,4-dihydro- [1, 2,4] triazole-3-thione 1-3 2- [rel (2R, 3S) - (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -2,4-dihydro- [1,2,4] triazole 3-thione I-4 1 - [rel (2R, 3S) -2- (3-fluorophenyl) -3- (2-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1 H- [1,2,4] triazole I-5 1 - [rel (2R, 3S) -2- (3-fluorophenyl) -3-o-tolyl-oxiranylmethyl] -5-methylsulfanyl-1H- [1, 2,4] triazole I-6 1 - [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methylsulfanyl-1 H- [1, 2,4] triazole 1-7 [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-methanesulfonyl-1 H- [1,2,4] triazole 1-8 thiocarbonic acid S- {2-rel (2R, 3S) - [3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H- [1,2,4] triazol-3-yl ester methyl ester I-9 1 - [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -5-thiocyanato 1 H- [1,2,4] triazole 1-10 thioacetic acid S- {2- [rel (2R, 3S) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiranylmethyl] -2H- [ 1, 2,4] triazol-3-yl} ester 6. Fungicidal mixtures according to one of claims 1 to 5, wherein the component 2 is selected from the following compounds: 11-1 epoxiconazole II-2 metconazole 11 -3 tebuconazole II-4 fluquinconazole II-5 Flutriafol II-6 Triticonazole II-7 prothioconazole II-8 kresoxim-methyl II-9 Pyraclostrobin 11-10 Orysastrobin 11-1 1 dimethomorph 11-12 5-Ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidines-7-ylamines 11-13 pyrimethanil 11-14 metalaxyl 11-15 fenpropimorph 11-16 dodemorph 11-17 iprodione 11-18 Mancozeb 11-19 Metiram II-20 thiophanate-methyl 11-21 chlorothalonil II-22 Metrafenone II-23 Bixafen 11-24 Boscalid 11-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide II-26 Sedaxane II-27 isopyrazam II-28 Fluopyram II-29 Penflufen 7. Fungicidal mixtures according to claim 1, wherein the mixture is selected from the following binary mixtures: - I-5 and Boscalid II-24 - I-5 and Orysastrobin 11-10 - I-7 and Boscalid II-24 - I-3 and epoxiconazole 11-1 - l-3 and boscalid II-24 - 1-1 and boscalid II-24 wherein the compounds 1-1, I-3, I-5, I-7 are the compounds defined in claim 5. 8. Fungicidal mixtures according to one of claims 1 to 6, wherein the component 3 is selected from the following connections: 11-1 epoxiconazole II-2 metconazole 11- 3 tebuconazole II-6 triticonazole II-7 prothioconazole II-8 kresoxim-methyl II-9 Pyraclostrobin 11-1 1 Dimethomorph 11-12 5-Ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidines-7-ylamine 11-13 pyrimethanil 11-14 metalaxyl 11-15 fenpropimorph 11-18 Mancozeb 11-19 Metiram II-20 thiophanate-methyl 11-21 chlorothalonil II-22 Metrafenone II-23 Bixafen II-24 boscalid II-25 N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 11-26 Sedaxanes 11-27 Isopyrazam 11-28 Fluopyram 11-29 Penflufen 9. Fungicidal mixtures according to one of claims 1 to 8, containing one of the components 1 and one of the components 2 in a weight ratio of 100: 1 to 1: 100. 10. Fungicidal mixtures according to one of claims 1 to 6 or 8 to 9, comprising one of the components 2 and one of the components 3 in a weight ratio of 100: 1 to 1: 100. 1 1. Use of a fungicidal mixture according to any one of claims 1 to 10 for controlling phytopathogenic fungi. 12. An agrochemical composition containing a solvent or solid carrier and a fungicidal mixture according to any one of claims 1 to 10. 13. Seed containing a fungicidal mixture according to any one of claims 1 to 10. 14. A method for controlling phytopathogenic fungi, characterized in that the fungi, or to be protected from fungal attack materials, plants, the soil or seeds with an effective amount of a fungicidal Mixture according to one of claims 1 to 10 treated.