WO2011110583A2 - Fungicidal mixtures comprising triazole derivatives - Google Patents

Fungicidal mixtures comprising triazole derivatives Download PDF

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WO2011110583A2
WO2011110583A2 PCT/EP2011/053519 EP2011053519W WO2011110583A2 WO 2011110583 A2 WO2011110583 A2 WO 2011110583A2 EP 2011053519 W EP2011053519 W EP 2011053519W WO 2011110583 A2 WO2011110583 A2 WO 2011110583A2
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ii
ci
cs
according
mixture
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PCT/EP2011/053519
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WO2011110583A3 (en
Inventor
Jochen Dietz
Jens Renner
Marianna Vrettou-Schultes
Egon Haden
Richard Riggs
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Basf Se
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Priority to US31231410P priority Critical
Priority to EP10156143.9 priority
Priority to US61/312,314 priority
Priority to EP10156143 priority
Priority to EP10156311.2 priority
Priority to EP10156311 priority
Priority to EP10196389.0 priority
Priority to EP10196389 priority
Application filed by Basf Se filed Critical Basf Se
Publication of WO2011110583A2 publication Critical patent/WO2011110583A2/en
Publication of WO2011110583A3 publication Critical patent/WO2011110583A3/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Abstract

Fungicidal mixtures comprising, as active components, 1) a triazolyl compound selected from the compounds of the formula (I) in which the variables have the meanings as defined in the description and the claims, and a component 2.

Description

Fungicidal mixtures Description The present invention relates to pesticidal mixtures, in particular fungicidal mixtures and compositions comprising, as active components,

1 ) a triazolyl co of the formula I

Figure imgf000002_0001

in which the variables have the following meanings:

X is H or D; where D is as defined below:

D - is S-R10, where

R10 is hydrogen, Ci-Cs-alkyI, Ci-Ce-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C(=0)R11, C(=S)R11, S02R12 or CN; where R11 is Ci-C8-alkyl, Ci-C8-haloalkyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy or NA3A4, where A3 and A4 are as defined below:

A3,A4 independently of one another are hydrogen, Ci-C8-alkyl, Ci-C8-haloalkyl, C3-C8-cycloalkyl, phenyl;

R12 is Ci-C8-alkyl, phenyl-Ci-C8-alkyl or phenyl, where the phenyl groups are in each case unsubstituted or substituted by one, two or three groups independently selected from the group consisting of halogen and Ci-C4-alkyl;

- is a group Dl

Figure imgf000003_0001

where the variables are as defined above; - is a group DM

Figure imgf000003_0002

where # is the point of attachment to the azolyl ring and Q, R13 and R14 are as defined below:

Q is O or S;

R13, R14 independently of one another are Ci-Cs-alkyl, Ci-Cs- haloalkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, C3-C8-cycloalkyl, phenyl, phenyl-Ci-C4-alkyl, phenoxy, phenyl-Ci-C4- alkoxy or NR15R16, where R15 is H or d-Cs-alkyl and R16 is Ci-C8- alkyl, phenyl-Ci-C4-alkyl or phenyl;

or

- is a group SM, where M is as defined below:

M is an alkali metal cation, an equivalent of an alkaline earth metal cation, an equivalent of a copper, zinc, iron or nickel cation or an amm ula (E)

Figure imgf000003_0003
in which

E1 and E2 independently of one another are hydrogen or Ci-Cs-alkyl; E3 and E4 independently of one another are hydrogen, Ci-Cs-alkyl, benzyl or phenyl; where the phenyl groups are in each case unsubstituted or substituted by one, two or three groups

independently of one another selected from the group consisting of halogen and Ci-C4-alkyl; r a single bond to R1; Z is a saturated hydrocarbon chain which has two to five carbon atoms and which may contain one, two or three substituents Rz, where Rz is as defined below: Rz is halogen, C-i-Cs-alkyl, C-i-Cs-haloalkyl, C2-Cs-alkenyl, C2-Cs-halo- alkenyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, C2-C8- alkenyloxy, C2-C8-haloalkenyloxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cyclo- alkenyloxy, Ci-C6-alkylene, oxy-C2-C4-alkylene, phenoxy, phenyl; where Rz is in each case unsubstituted or contains one, two or three independently selected groups L; is phenyl which is unsubstituted or contains one, two, three, four or five independently selected substituents L, where L is as defined below:

L is halogen, C-i-Cs-alkyl, Ci-Cs-haloalkyl, C2-Cs-alkenyl, C2-Cs-halo- alkenyl, C4-Cio-alkadienyl, C4-Cio-haloalkadienyl, Ci-Cs-alkoxy, Ci- Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, C2-Cs-alkenyloxy, C2-Cs-halo- alkenyloxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, C3-Cs-halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cycloalkenyloxy, Ci- C6-alkylene, the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:

RL is halogen, hydroxy, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocyclo- alkyl, Cs-Cs-cycloalkenyl, Cs-Cs-cycloalkoxy, Cs-Cs-halocycloalkoxy, Ci-C6-alkylene, oxy-C2-C4-alkylene, oxy-Ci-C3-alkyleneoxy, Ci-Cs- alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkoxycarbonyl, amino, Ci-Ce-alkylamino, di-C-i-Cs-alkylamino; is hydrogen, halogen , Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio- haloalkenyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl;

R3 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-halo- alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3-C10- cycloalkenyl, C3-Cio-halocycloalkenyl, tri-Ci-Cio-alkylsilyl; R4 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-halo- alkenyl, C3-Cio-cycloalkyl;

R2, R3 and R4 are, unless indicated otherwise, independently of one another unsubstituted or substituted by one, two, three, four or five L, as defined above; and agriculturally acceptable salts thereof; and 2) a fungicidal compound II selected from the following compounds:

A) strobilurins:

azoxystrobin, dimoxystrobin, coumoxystrobin, coumethoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2- (6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)phenyl)-2-methoxyimino- N-methylacetamide, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-

3- methoxyacrylate, methyl 3-methoxy-2-(2-(N-(4-methoxyphenyl)- cyclopropanecarboximidoylsulfanylmethyl)phenyl)acrylate, 2-(2-(3-(2,6-dichloro- phenyl)-1 -methylallylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methyl- acetamide;

B) carboxamides:

carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kira- laxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-

4- methylthiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethylindan-4- yl)nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide, N-(2-(1 ,3-dimethylbutyl)phenyl)-1 ,3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide (penflufen), N-(2-(1 ,3,3- trimethylbutyl)phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;

carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;

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

other carboxamides: carpropamid, diclocymet, mandipropamid,

oxytetracyclin, 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: cyazofamid, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;

benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

others: ethaboxam, etridiazole, hymexazole, 2-(4-chlorophenyl)-N-[4-(3,4- dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;

D) nitrogenous heterocyclyl compounds

pyridines: fluazinam, pyrifenox, 3-[5-(4-chlorophenyl)-2,3- dimethylisoxazolidin-3-yl]pyridine, 3-[5-(4-methylphenyl)-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-chloropyridin-2-yl)ethyl)-2,4- dichloronicotinamide, N-((5-bromo-3-chloro-pyridin-2-yl)methyl)-2,4- dichloronicotinamide;

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

piperazines: triforine;

- pyrroles: fludioxonil, fenpiclonil;

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

piperidines: fenpropidin;

dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;

- nonaromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, S-allyl 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3- d i hyd ro py razo I e- 1 -t h i oca rboxy I a te ;

others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzo- quat-methylsulfate, fenoxanil, folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-

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]pyrimidin-7-ylamine;

E) carbamates and dithiocarbamates

thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,

methasulfocarb, metiram, propineb, thiram, zineb, ziram;

carbamates: diethofencarb, benthiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, valiphenal, 4-fluorophenyl N-(1 -(1 -(4- cyanophenyl)ethanesulfonyl)but-2-yl)carbamate;

F) other fungicides guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate);

antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;

- nitrophenyl derivatives: binapacryl, dicloran, dinobuton, dinocap, nitrothal isopropyl, tecnazene;

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

sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;

- organophosphorus compounds: edifenphos, fosetyl, fosetyl aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;

organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide,

quintozene, thiophanate methyl, tolylfluanid, N-(4-chloro-2-nitrophenyl)-N-ethyl-4- methylbenzenesulfonamide;

inorganic active compounds: phosphorous acid and its salts, Bordeaux mixture, copper salts, such as, for example, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

- others: 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- trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine, N'-(4- (4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N- methylformamidine, N'-(2-methyl-5-trifluoromethyl-4-(3- trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine, N'-(5- difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N- methylformamidine, methyl N-(1 ,2,3,4-tetrahydronaphthalen-1 -yl)-2-{1 -[2-(5- methyl-3-trifluoromethylpyrazol-1 -yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, methyl (R)-N-(1 ,2,3,4-tetrahydronaphthalen-1 -yl)-2-{1 -[2-(5-methyl-3- trifluoromethylpyrazol-1 -yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, 6-tert- butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate, 6-tert-butyl-8-fluoro-2,3- dimethylquinolin-4-yl methoxyacetate, N-methyl-2-{1 -[2-(5-methyl-3-trifluoro- methyl-1 H-pyrazol-1 -yl)acetyl]piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydro- naphthalen-1 -yl]-4-thiazolecarboxamide;

G) growth regulators

abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 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, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapac-ethyl and uniconazole;

H) herbicides

acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;

amino acid analogs: bilanafos, glyphosate, glufosinate, sulfosate;

- aryloxyphenoxypropionat.es: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-p-tefuryl; bipyridyls: diquat, paraquat;

carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;

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

dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;

- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil;

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, norflurazone, pyridate; pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;

- sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, fluce- tosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron,

iodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, 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, metamitron, 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, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;

others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzo- quat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate,

etobenzanid, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam,

fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methylarsenic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraf I uf en-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, 4-hydroxy-3-[2-(2-methoxyethoxymethyl)-6- trifluoromethylpyridine-3-carbonyl]bicyclo[3.2.1 ]oct-3-en-2-one, ethyl (3-[2-chloro- 4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 - yl)phenoxy]pyridin-2-yloxy)acetate, methyl 6-amino-5-chloro- 2-cyclopropylpyrimidine-4-carboxylate, 6-chloro-3-(2-cyclopropyl-6- methylphenoxy)pyridazin-4-ol, 4-amino-3-chloro-6-(4-chlorophenyl)-5- fluoropyridine-2-carboxylic acid, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro- 3-methoxyphenyl)pyridine-2-carboxylate and methyl 4-amino-3-chloro-6-(4- chloro-3-dimethylamino-2-fluorophenyl)pyridine-2-carboxylate;

I) insecticides

organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, 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, triazamate;

pyrethroids: allethrin, bifenthrin, cyfluthrin, beta-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,

inhibitors of insect growth: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazin; b) ecdysone antagonists:

halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids:

pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors:

spirodiclofen, spiromesifen, spirotetramate;

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, ethiprol, fipronil, vaniliprol, pyrafluprol, pyriprol, 5-amino-1 -(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1 H-pyrazole-3- thiocarboxamide;

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; decouplers: chlorfenapyr;

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

- insect molting inhibitors: cryomazine;

mixed function oxidase inhibitors: piperonyl butoxide;

sodium channel blockers: indoxacarb, metaflumizone;

others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamid, chlorantraniliprol, cyazypyr (HGW86);

cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyrifluquinazon and and [(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 cyclopropanecarboxylate;

in a synergistically effective amount.

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

antifungal biocontrol agents, plant bioactivators: Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g.

AFLAGUARD® from Syngenta, CH), Aureobasidium pullulans (e.g. BOTECTOR® from bio-ferm GmbH, Germany), Bacillus pumilius (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from Fa. AgraQuest Inc., USA), Bacillus subtilis var. amyloliquefaciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE® (in mixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France),

Metschnikowia fructicola (e.g. SHEMER® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT® from Agrauxine, France), Phlebiopsis gigantea (e.g.

ROTSOP® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g.

REGALIA® from Marrone Biolnnovations, USA), Talaromyces flavus V1 17b (e.g.

PROTUS® from Prophyta, Germany), Trichoderma asperellum SKT-1 (e.g. ECO- HOPE® from Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T. harzianum T-22 (e.g.

PLANTSHIELD® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX® and

TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g. BINAB® from BINAB Bio-Innovation AB, Sweden), T. stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C., Brazil), T. virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), T. viride {e.g. TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), T. viride TV1 (e.g. T. viride TV1 from Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN® from Botry-Zen Ltd, NZ), wherein the components 1 ) and 2) are present in a synergistic amount. The present invention furthermore provides mixtures which, in addition to the components 1 ) and 2) mentioned above, comprise at least one component 3) selected from the compounds II of groups A) to I) mentioned for component 2), provided all components are different from one another. The present invention also provides mixtures which, in addition to the components 1 ), 2) and 3) mentioned above, comprise at least one further compound II as additional components (for example component 4 or components 4 and 5), where the compound II of the additional components (for example component 4 or components 4 and 5) is independently selected from the compounds mentioned above of groups A) to I), provided all components are different from one another.

According to this subject matter, the present invention relates in particular to synergistic mixtures which, in addition to the components 1 ), 2) and 3) defined above, comprise one further compound II as 4th component, where this component 4) is selected from from the compounds defined above of groups A) to I), provided the components 2), 3) and 4) are different from one another.

The invention furthermore relates to the use of the fungicidal mixtures according to the invention for controlling phytopathogenic fungi, and to preparations or compositions comprising them. The invention furthermore also relates to seed comprising the fungicidal mixtures according to the invention. The invention furthermore also relates to methods for controlling phytopathogenic fungi wherein the fungi or the materials, plants, the soil or seeds to be protected from fungal attack are treated with an effective amount of a fungicidal mixture according to the invention. The invention furthermore also relates to processes for preparing the mixtures according to the invention.

Triazolylmethyloxiranes of component 1 ), their preparation and the precursors required, and their use in crop protection are disclosed in the patent applications WO

2010/029001 , WO 2010/029002, WO 2010/029000, WO 2010/029003, WO

2010/031721 , WO 2010/031847, WO 2010/031848, WO 2010/031842 and WO

2010/040718 (PCT/EP2009/061370, PCT/EP2009/061372, PCT/EP2009/061368, PCT/EP2009/061373, PCT/EP2009/061693, PCT/EP2009/062129,

PCT/EP2009/062130, PCT/EP2009/062122 and PCT/EP2009/062909), which also mention certain mixtures of the triazolylmethyloxiranes of component 1 ) with other active compounds.

The active compounds mentioned as component 2) and 3) and 4) or as "further active compound" above (compounds II), their preparation and their action against harmful fungi are known (cf.: http://www.alanwood.net/pesticides/); they are available commercially. The compounds with lUPAC nomenclature, their preparation, and their fungicidal activity are likewise known (cf. 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; DE 102005009458;

US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413;

WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ;

WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; 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 a view to reducing the application rates and broadening the activity spectrum of the known compounds, it was an object of the present invention to provide mixtures which, at a reduced total amount of active compounds applied, show improved activity against harmful fungi, in particular for certain indications. Accordingly we have found the mixtures defined at the outset.

According to one embodiment, the invention relates to fungicidal mixtures comprising

1 ) triazolylmethyloxiranes of the formula I as described above; and

2) a fungicidal compound II selected from the compounds of groups A to I as described above,

in a synergistically effective amount.

According to a further embodiment, the invention relates to fungicidal mixtures comprising

1 ) triazolylmethyloxiranes of the formula I as described above; and

2) a fungicidal compound II; and

3) a further fungicidal compound II,

where the compounds II of components 2) and 3) independently of one another are selected from the compounds of groups A to I as described above, with the proviso that component 2) and component 3) are not identical,

in a synergistically effective amount.

According to a further embodiment, the invention relates to fungicidal mixtures comprising

1 ) triazolylmethyloxiranes of the formula I as described above; and

2) a fungicidal compound II; and

3) a further fungicidal compound II; and

4) a further fungicidal compound II,

where the compounds II of components 2), 3) and 4) independently of one another are selected from the compounds of groups A to I as described above, with the proviso that components 2), 3) and 4) are different from one another, in a synergistically effective amount.

The mixtures according to the invention are preferably binary mixtures, particularly preferably ternary mixtures. Accordingly, the present invention relates in particular also to pesticidal compositions which comprise at least one compound of the general formula I and at least one further active compound (component 2 and optional component 3), for example one or more, for example 1 or 2, active compounds of groups A to I mentioned above and, optionally, one or more agriculturally suitable carriers. The present invention furthermore also relates to pesticidal compositions which comprise at least one compound of the general formula I and at least three further active compounds

(components 2, 3 and 4) of groups A to I mentioned above and, optionally, one or more agriculturally suitable carriers. Moreover, it has been found that simultaneous, that is joint or separate, application of compound I and one or more compounds II, or compound I and compound(s) II applied in succession, allows better control of pests, in particular harmful fungi than with the individual compounds (synergistic mixtures). As mentioned above, these mixtures are of interest with a view to reducing the application rates, since many show, at a reduced total amount of active compounds applied, an improved activity against harmful fungi, in particular for certain indications.

Simultaneous, that is joint or separate, application of compound I and one or more compounds II can increase the fungicidal activity in a superadditive manner.

In the sense of the present application, joint application means that at least one compound I and the at least one further active compound II are present simultaneously at the site of action (i.e. the plant-damaging fungi to be controlled and their habitat, such as infected plants, plant propagation materials, in particular seed, soils, materials or spaces and also the plants, plant propagation materials, in particular seed, soils, materials or spaces to be protected against fungal attack) in an amount sufficient for an effective control of fungal growth. This can be achieved by applying the compounds I and at least one further active compound II jointly in a joint active compound preparation or in at least two separate active compound preparations simultaneously, or by applying the active compounds successively to the site of action, the time interval between the individual active compound applications being chosen such that the active compound applied first is, at the time of application of the further active compound(s), present at the site of action in a sufficient amount. The order in which the active compounds are applied is of minor importance.

In a preferred embodiment, the mixtures are binary mixtures, i.e. compositions according to the invention comprising one compound I and one further active compound II (component 2), for example one active compound from groups A) to I). Here, the weight ratio of compound I to further active compound II depends on the properties of the active compounds in question; usually, it is in the range of from 1 :100 to 100:1 , frequently in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , particularly preferably in the range of from 1 :10 to 10:1 , in particular in the range of from 1 :3 to 3:1 . In a further preferred embodiment, the mixtures are ternary mixtures, i.e.

compositions according to the invention comprising one active compound I and one 1 st further active compound (component 2) and one 2nd further active compound

(component 3), for example two different active compounds from groups A) to I). Here, the weight ratio of compound I to the 1st further active compound (component 2) depends on the properties of the active compounds in question; preferably, it is in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of compound I to the 2nd further active compound (component 3) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of 1st further active compound (component 2) to 2nd further active compound (component 3) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 .

In a further preferred embodiment, the mixtures are quaternary mixtures, i.e.

compositions according to the invention comprising one active compound I and one 1 st further active compound II (component 2), one 2nd further active compound II

(component 3) and one 3rd further active compound (component 4), where these three active compounds II are different active compounds independently selected from groups A) to I). Here, the weight ratio of compound I to the 1st further active compound (component 2) depends on the properties of the active compounds in question;

preferably, it is in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of compound I to the 2nd further active compound (component 3) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of compound I to the 3rd further active compound (component 4) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of 1st further active compound (component 2) to 2nd further active compound (component 3) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of 1st further active compound (component 2) to 3rd further active compound (component 4) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :10 to 10:1 . The weight ratio of 2nd further active compound (component 2) to 3rd further active compound (component 4) is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 , and in particular in the range of from 1 :10 to 10:1 . The components of the composition according to the invention can be packaged and used individually or as a ready-mix or as a kit of parts. In one aspect of the invention, the kits may comprise one or more, and even all, components which may be used for preparing an agrochemical composition according to the invention. For example, these kits may comprise one or more fungicide components and/or an adjuvant component and/or an insecticide component and/or a growth regulator component and/or a herbicide. One or more components may be present combined or preformulated with one another. In the aspects where more than two components are provided in a kit, the components can be present combined with one another and packaged in a single container, such as a vessel, a bottle, a tin, a bag, a sack or a canister. In other embodiments, two or more components of a kit may be packaged separately, i.e. not preformulated or mixed. Kits may comprise one or more separate containers, such as vessels, bottles, tins, bags, sacks or canisters, each container comprising a separate component of the agrochemical composition. The components of the composition according to the invention can be packaged and used individually or as a ready-mix or as a kit of parts. In both forms, a component may be used separately or together with the other components or as a part of a kit of parts according to the invention for preparing the mixture according to the invention.

The user uses the composition according to the invention usually for use in a predosage device, a knapsack sprayer, a spray tank or a spray plane. Here, the agrochemical composition is diluted with water and/or buffer to the desired application concentration, with further auxiliaries optionally being added, thus giving the ready-to- use spray liquor or the agrochemical composition according to the invention. Usually, from 50 to 500 liters of the ready-to-use spray liquor are applied per hectare of agricultural utilized area, preferably from 100 to 400 liters.

According to one embodiment, the user may himself mix individual components, such as, for example, parts of a kit or a two- or three-component mixture of the composition according to the invention in a spray tank and, optionally, add further auxiliaries (tank mix).

In a further embodiment, the user may mix both individual components of the composition according to the invention and partially pre-mixed components, for example components comprising compounds I and/or active compounds from groups A) to I), in a spray tank and, optionally, add further auxiliaries (tank mix).

In a further embodiment, the user may use both individual components of the composition according to the invention and partially pre-mixed components, for example components comprising compounds I and/or active compounds from groups A) to I), jointly (for example as a tank mix) or in succession.

Owing to the basic character of their nitrogen atoms, the compounds I are capable of forming salts or adducts with inorganic or organic acids or with metal ions. This also applies to most of the precursors described herein of compounds I, the salts and adducts of which are also provided by 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 also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other

arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphoric acid radicals), where 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.

Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and also of the elements of transition groups one to eight, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc, and others.

Particular preference is given to the metal ions of the elements of transition groups of the fourth period. The metals can be present in the various valencies that they can assume.

The compounds I contain centers of chirality and are generally obtained in the form of racemates or as diastereomer mixtures of erythro and threo forms. The erythro and threo diastereomers of the compounds according to the invention can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers. Suitable for use as antimicrobial agents are both the uniform diastereomers or enantiomers and mixtures thereof obtained in the synthesis. This applies correspondingly to the pesticidal compositions. Accordingly, the invention provides both mixtures in which compound I is the pure enantiomers or diastereomers and mixtures thereof. This applies to the mixtures according to the invention of the compounds of the formula I. The scope of the present invention includes in particular the (R) and (S) isomer mixtures and the racemates of the compounds I which have centers of chirality. Suitable compounds I also comprise all possible stereoisomers (cis/trans isomers) and mixtures thereof. In some of the definitions of the symbols in the formulae given herein, 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, for example, alkylamino: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C6-alkyl, such as methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-me- thylbutyl, 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-dime- thylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-tri- methylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methyl propyl; haloalkyi: alkyl as mentioned above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above; in particular C1-C2- 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 also the alkenyl moieties in composite 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 one double bond in any position. According to the invention, it may be preferred to use small alkenyl groups, such as (C2-C4)-alkenyl; on the other hand, it may also be preferred to employ larger alkenyl groups, such as (C5-C8)-alkenyl. Examples of alkenyl groups are, for example, C2-C6-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, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by 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 and the alkynyl moieties in composite groups: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-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-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl-1 -methyl-2- propynyl; haloalkynyl: alkoxy as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; cycloalkyi and also the cycloalkyi moieties in composite groups: mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; halocydoalkyi: cycloalkyi as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by 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, cyclohexen-4-yl and the like; halocycloalkenyl: cycloalkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; alkoxy: an alkyl group as defined above which is attached via an oxygen, preferably having 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, and also, for example, 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, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine. Examples are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 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, OC2F5, 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-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromoethoxy, 4- fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5- fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy; alkylene: divalent unbranched chains of CH2 groups. Preference is given to (C1-C6)- alkylene, more preference to (C2-C4)-alkylene; furthermore, it may be preferred to use (Ci-C3)-alkylene groups. Examples of preferred alkylene radicals are CH2, CH2CH2, CH2CH2CH2, CH2(CH2)2CH2, CH2(CH2)3CH2 and CH2(CH2)4CH2; In the compounds I (component 1 ) of the mixtures according to the invention, particular preference is given to the following meanings of the substituents, in each case on their own or in combination.

In a preferred embodiment, the present invention relates to mixtures in which component 1 ) is selected from compounds of the formula I in which the variables have the following meanings:

According to one embodiment of the invention, X is hydrogen (compounds 1.1 ).

According to one embodiment of the invention, X is D (compounds 1.2), where D has the meanings given above.

Compounds of the formula I in which X = D (compounds I.2), in particular in which D is SH, can be present in the "thiol" form of the formula 1.2a or in the "thiono" form of the formula 1.2b:

Figure imgf000021_0001
in which D* is as defined below:

- R10, where R10 has the meaning given above;

- a group DM*

Figure imgf000021_0002
where # is the point of attachment to the sulfur atom in formula 1.2a or to the azolyl ring in formula 1.2b and Q, R13 and R14 have the meaning defined above; or

- a group M, where M has the meaning defined above,

and in which the remaining substituents have the meaning defined above.

For the sake of simplicity, in general only one of the two forms, in most cases the "thiol" form, is shown in each case.

According to one aspect, D is SH. According to a further aspect, D is S-R10 where R10 is d-Cs-alkyl or C-i-Cs-haloalkyl, in particular Ci-C4-alkyl, especially methyl or ethyl.

According to a further aspect, D is S-R10 where R10 is C2-C8-alkenyl or C2-Cs- haloalkenyl.

According to yet a further aspect, D is S-R10 where R10 is CN.

According to a further embodiment of the invention, D is S-R10 where R10 is C(=0)R11 and R11 is NA3A4, where A3 and A4 independently of one another are hydrogen or Ci- Ce-alkyl. According to one aspect, one of the radicals A3 and A4 is phenyl. According to a further aspect, R11 is (Ci-C4)-alkylamino or di-(Ci-C4)-alkylamino. According to a further aspect, R11 is methylamino, dimethylamino, ethylamino, diethylamino or phenylamino.

According to a further embodiment of the invention, D is S-R10 where R10 is C(=0)R11 and R11 is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy. According to a further aspect thereof, R11 is methyl or ethyl, preferably methyl. According to yet a further aspect, R11 is trifluoromethyl. According to yet a further aspect, R11 is methoxy or ethoxy.

According to a further embodiment of the invention, D is S-R10 where R10 is SO2R12 and R12 is Ci-C4-alkyl, phenyl-Ci-C4-alkyl or phenyl, where the phenyl groups are in each case unsubstituted or substituted by one, two or three groups independently selected from the group consisting of halogen and Ci-C4-alkyl.

According to a further embodiment of the invention, D is a group SM where M is an alkali metal cation, an equivalent of an alkaline earth metal cation, an equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula Formel (E)

E2

E1— N-Z3 (E)

in which

E1 and E2 independently of one another are hydrogen or Ci-C4-alkyl; and E3 and E4 independently of one another are hydrogen, Ci-C4-alkyl, benzyl or phenyl. According to one embodiment, M is Na, 1/2 Cu, 1/3 Fe, HN(CH3)3, HN(C2H5)3, N(CH3)4 or

H2N(C3H7)2, in particular Na, 1/2 Cu, HN(CH3)3 or HN(C2H5)3, especially Na, 1/2 Cu, HN(CH3)3 or HN(C2H5)3. According to a further embodiment of the invention, D is a group Dl (-> compounds 1.2 dimer), where the other variables are as defined herein or as defined as being preferred.

Figure imgf000023_0001

In the compounds 1.2 dimer, R2, R3 and R4 are in particular hydrogen.

According to a further embodiment of the invention, D is a group DM

Figure imgf000023_0002

where # is the point of attachment to the triazolyl ring and Q, R13 and R14 are as defined below:

Q is O or S;

R13, R14 independently of one another are Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-cycloalkyl, phenyl, phenyl-Ci-C4- alkyl, phenoxy, phenyl-Ci-C4-alkoxy or NR15R16, where R15 is H or d-Cs-alkyl and R16 is Ci-Cs-alkyl, phenyl-Ci-C4-alkyl or phenyl.

According to one embodiment, Y According to a further embodiment, Y is a single bond to R1. According to a specific aspect thereof, Z is furthermore a saturated hydrocarbon chain which has three to five carbon atoms and which is unsubstituted or contains one, two or three substituents Rz, where Rz is independently as defined herein or as defined as being preferred. In the compounds according to the invention, Z is a saturated hydrocarbon chain which has two to five carbon atoms and which is unsubstituted or contains one, two or three substituents Rz. According to one aspect thereof, Z is an optionally substituted saturated hydrocarbon chain which has three to five carbon atoms, in particular three or four carbon atoms.

According to one embodiment, Z is unsubstituted. According to a further embodiment, Z contains at least one substituent Rz, as defined herein or as defined as being preferred.

According to a further embodiment of the invention, Z is a group Z1:

Figure imgf000024_0001

in which # denote the points of attachment and n is 2, 3, 4 or 5, in particular 3 or 4. Rz1 and Rz2 are each independently of one another selected from the group consisting of hydrogen and Rz. In particular, Rz1 and Rz2 are each independently of one another selected from the group consisting of hydrogen and Ci-C4-alkyl and C3-C6-cycloalkyl and/or Rz1 and Rz2 together with the carbon to which they are attached form a d-d- cycloalkyl ring. In a further aspect, Rz is selected from the group consisting of F and CI.

In a specific embodiment of the invention, all radicals Rz1 and Rz2 in Z1 are hydrogen.

According to one embodiment, n in group Z1 is 2.

According to one embodiment, n in group Z1 is 3. According to a specific embodiment, Y is simultaneously a bond.

According to a further embodiment, n in group Z1 is 4. According to a specific embodiment, Y is simultaneously O.

According to a further embodiment, n in group Z1 is 5.

According to a further embodiment, Z is Z1 in which n = 3, 4 or 5 and Y is is a single bond between R1 and Z.

Unless indicated otherwise, the substituent(s) Rz at Z or in group Z1 is/are in each case independently selected from the group consisting of halogen, d-Cs-alkyl, Ci-d- haloalkyl, d-d-alkenyl, C2-C8-haloalkenyl, Ci-d-alkoxy, d-Cs-haloalkoxy, Ci-d- alkylcarbonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, d-d-cycloalkyl, d-d- halocycloalkyl, d-d-cycloalkenyl, d-d-halocycloalkenyl, d-d-cycloalkoxy, d-d- cycloalkenyloxy, Ci-C6-alkylene, oxy-C2-C4-alkylene, phenoxy, phenyl; where Rz is in each case unsubstituted or contains one, two or three independently selected groups L.

According to one embodiment, Rz is in each case independently halogen, Ci-d-alkyl, Ci-Cs-haloalkyl, d-d-alkenyl, C2-C8-haloalkenyl, Ci-d-alkoxy, d-Cs-haloalkoxy, Ci- d-alkylcarbonyloxy, d-d-alkenyloxy, d-d-haloalkenyloxy, Cs-Cs-cycloalkyl, d-d- halocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, Cs-Cs-cycloalkoxy or d-d- cycloalkenyloxy. According to a further aspect, Rz is in each case independently CI, F, Br, Ci-d-alkyl, Ci-d-haloalkyl, d-d-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C3-C6-cycloalkyl or C3-C6-halocycloalkyl, in particular methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyclopropyl.

According to a further embodiment, at least one Rz is halogen, in particular CI or F.

According to a further embodiment, at least one Rz is Ci-C4-alkyl, in particular methyl or ethyl.

According to a further embodiment, at least one Rz is Ci-C4-haloalkyl.

According to a further embodiment, two radicals Rz which are attached to the same carbon atom form, together with the carbon atom to which they are attached, a C3-C6- cycloalkyl ring. In the compounds I, R1 is phenyl which is unsubstituted or contains one, two, three, four or five, in particular one, two or three, especially one or two, independently selected substituents L, as defined herein or as defined as being preferred. R1 is preferably substituted. According to a further embodiment, R1 is phenyl which contains exactly one substituent L1. According to one aspect thereof, L1 is selected from the group consisting of F, CI, Br, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl, in particular F, CI, Br, methyl, trifluoromethyl, difluoromethyl and methoxy. According to a specific embodiment thereof, L1 is selected from the group consisting of F, CI and Br.

According to a further embodiment, R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L, L1 and L2 are defined like L (see below). According to one aspect, L1 and L2 are each independently selected from the group consisting of CI, F, Br, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and the further one, two or three, preferablyy the one, substituent optionally present is/are

independently selected from L, as defined herein or as defined as being preferred. According to a further embodiment, R1 is phenyl which may contain one substituent L1 which is CI and additionally also one, two, three or four independently selected substituents L, where the radicals L are in each case independently as defined herein. According to one aspect, the phenyl group is substituted in position 2 by CI. According to a further aspect, the phenyl group of this embodiment is substituted in position 3 by CI. According to yet a further aspect, the phenyl group of this embodiment is substituted in position 4 by CI. According to a further aspect, the phenyl group is substituted by CI and contains exactly one further substituent L2. According to one aspect, the phenyl group is 2,3- disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.

According to a further aspect, the phenyl group is substituted by CI and contains exactly two further substituents, L2 and LA

According to a further embodiment, R1 is phenyl which may contain one substituent L1 which is F and additionally also one, two, three or four independently selected substituents L, where the radicals L are in each case independently as defined herein. According to one aspect thereof, the phenyl group is substituted in position 2 by F. According to a further aspect, the phenyl group of this embodiment is substituted in position 3 by F. According to yet a further aspect, the phenyl group of this embodiment is substituted in position 4 by F.

According to a further embodiment, the phenyl group is substituted by F and contains exactly one further substituent L2. According to one aspect, phenyl group is 2,3- disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted. Here, F is preferably located in position 2 or 4, according to one aspect in position 2. More preferably, the second substituent L2 is selected from the group consiting of F, CI, Br, methyl and methoxy. According to a specific embodiment, the phenyl group is 2,3-, 2,4-, 2,5- or 2,6-difluoro- substituted. According to a further specific embodiment, the phenyl group is 2-fluoro-3- chloro-, 2-fluoro-4-chloro-, 2-fluoro-5-chloro- or 2-fluoro-6-chloro-substituted. According to a further aspect, the phenyl group is substituted by F and contains exactly two further substituents, L2 and LA

According to a further embodiment, R1 is phenyl which may contain one substituent L1 which is methyl and additionally also one, two, three or four independently selected substituents L, where the radicals L are in each case independently as defined herein. According to one aspect thereof, the phenyl group is substituted in position 2 by methyl. According to a further aspect, the phenyl group of this embodiment is substituted in position 3 by methyl. According to yet a further aspect, the phenyl group of this embodiment is substituted in position 4 by methyl. According to a further aspect, the phenyl group is substituted by methyl (=L1) and contains exactly one further substituent L2. According to one aspect, phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.

According to a further aspect, the phenyl group is substituted by methyl (=L1) and contains exactly two further substituents, L2 and L3. According to a further embodiment, R1 is phenyl which may contain one substituent L1 which is methoxy and additionally also one, two, three or four independently selected substituents L, where the radicals L are in each case independently as defined herein. According to one aspect thereof, the phenyl group is substituted in position 2 by methoxy. According to a further aspect, the phenyl group of this embodiment is substituted in position 3 by methoxy. According to yet a further aspect, the phenyl group of this embodiment is substituted in position 4 by methoxy.

According to a further aspect, the phenyl group is substituted by methoxy (=L1) and contains exactly one further substituent L2. According to one aspect, the phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.

According to a further aspect, the phenyl group is substituted by methoxy (=L1) and contains exactly two further substituents, L2 and L3.

According to a further embodiment, R1 is phenyl which contains three, four or five substituents L, where L is independently as defined herein or as defined as being preferred.

According to a further embodiment of the invention, R1 is a 2,3,5-trisubstituted phenyl ring. According to a further embodiment, R1 is a 2,3,4-trisubstituted phenyl ring.

According to yet a further embodiment, R1 is a 2,4,5-trisubstituted phenyl ring.

According to yet a further embodiment, R1 is a 2,4,6-trisubstituted phenyl ring.

According to yet a further embodiment, R1 is a 2,3,6-trisubstituted phenyl ring.

According to one aspect, at least one of the three substituents is CI. According to one aspect, at least one of the three substituents is F. According to a further aspect, at least one of the three substituents is methyl. According to yet a further aspect, at least one of the three substituents is methoxy. According to a further embodiment, R1 is phenyl which is disubstituted by two L, where L is in each case independently selected from the group consisting of CI, F, Br, C1-C4- alkyl and Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. According to a specific aspect, L is in each case independently selected from the group consisting of CI, F, Ci- C4-alkyl and Ci-C4-haloalkyl. According to a further specific aspect, L is in each case independently selected from the group consisting of CI, F, Br, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy.

L has independently the meanings or preferred meanings for L mentioned above or in the claims. According to one aspect thereof, L is not substituted any further by RL.

Unless indicated otherwise, L is preferably independently selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3- C6-cycloalkyl and C3-C6-halocycloalkyl.

More preferably, L is independently selected from the group consisting of halogen, Ci- C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.

According to a further preferred embodiment, L is independently selected from the group consisting of F, CI, Br, CH3, C2H5, i-C3H7, t-C4H9, OCH3, OC2H5, CF3, CCI3,

CHF2, CCIF2, OCF3 and OCHF2, in particular selected from the group consisting of F, CI, CH3, C2H5, OCH3, OC2H5, CF3, CHF2, OCF3 and OCHF. According to one aspect, L isindependently selected from the group consisting of F, CI, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred for L to be independently F or CI.

According to a further embodiment, L is independently selected from the group consisting of F, Br, CH3, C2H5, i-C3H7, t-C4H9, OCH3, OC2H5, CF3, CCI3, CHF2, CCIF2,

Figure imgf000028_0001
According to yet a further embodiment, L is independently selected from the group consisting of F, CI, Br, methyl and methoxy.

According to the present invention, R2 is hydrogen, halogen, Ci-Cio-alkyl, C1-C10- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, where R2 may contain one, two, three, four or five substituents L, as defined herein. According to one embodiment, R2 is unsubstituted not further substituted, i.e. does not contain a substituent L. According to one embodiment, R2 is hydrogen, Ci-Cio-alkyl, Ci- Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, where R2 may contain one, two, three, four or five substituents L, as defined herein. According to one embodiment, R2 is unsubstituted not further substituted, i.e. does not contain a substituent L. According to a preferred embodiment, R2 is hydrogen.

According to a further embodiment, R2 is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, in particular Ci-C4-alkyl or C2-C4-alkenyl. Specific examples of R2 are methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-vinyl, 3-allyl.

According to a further embodiment, R2 is halogen, in particular F.

According to the present invention, R3 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2- Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3-Cio-cycloalkenyl, C3-Cio-halocycloalkenyl or tri-Ci-Cio-alkylsilyl, where R3 may contain one, two, three, four or five substituents L, as defined herein. According to one embodiment, R3 is unsubstituted not further substituted, i.e. does not contain a substituent L.

According to a preferred embodiment, R3 is hydrogen. Specific examples of R3 are trimethylsilyl, Si(CH3)2(CH2)3CH3, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-vinyl, 3-allyl, 3-propargyl and 4-but-2-ynyl.

According to a specific embodiment of the invention, R3 is trimethylsilyl. According to the present invention, R4 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2- Cio-alkenyl, C2-Cio-haloalkenyl, C3-Cio-cycloalkyl, where R4 may contain one, two, three, four or five substituents L, as defined herein. According to one embodiment, R4 is unsubstituted not further substituted, i.e. does not contain a substituent L. According to a preferred embodiment, R4 is hydrogen.

According to a further embodiment, R4 is Ci-C6-alkyl or C2-C6-alkenyl. Specific examples of R4 are methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl. According to a specific embodiment, R2, R3 and R4 are hydrogen.

Furthermore, if X in the compounds I is hydrogen (compounds (1.1 )), mixtures comprising the following compounds I, in particular binary mixtures, are specific embodiments a), b), c1 ), c2), d), e), f1 ), f2), g), hi ) and h2) of the invention:

Compounds I in which a) Y = O, Z is an unsubstituted saturated hydrocarbon chain having two carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-bromophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3- methylphenyl, 2-methylphenyl, 4-methylphenyl, 4-tert-butylphenyl, 3- trifluoromethylphenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 2-chloro-4-phenylphenyl or 3,5-dimethoxyphenyl; b) Y = O, Z is an unsubstituted saturated hydrocarbon chain having three carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl,

2- methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-methylphenyl, 3- trifluoromethylphenyl or 2,4-dichlorophenyl; c1 ) Y = O, Z is an unsubstituted saturated hydrocarbon chain having four carbon atoms, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl; c2) Y = O, Z is an unsubstituted saturated hydrocarbon chain having four carbon atoms, R2 and R3 are hydrogen and R4 is methyl or C2-Cio-alkenyl, and

R1 is as defined above or as defined above as being preferred, but not 4-fluorophenyl,

3- chlorophenyl, 4-chlorophenyl, 3-trifluoromethylphenyl or 2,4-dichlorophenyl; c3) Y = O, Z is an unsubstituted saturated hydrocarbon chain having four carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not 2-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, 3- methoxyphenyl, 4-methoxyphenyl, 3-n-butoxyphenyl, 3-tert-butoxyphenyl, 4- phenoxyphenyl, 3-(2-fluorophenoxy)phenyl, 3-(3-chlorophenoxy)phenyl, 2- methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-n-propylphenyl, 3-isopropylphenyl, 4- isopropylphenyl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3- phenylphenyl, 3-(3-chlorophenyl)phenyl, 3-(4-chlorophenyl)phenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 3,5-dichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 4- bromophenyl, 3-chloro-4-fluorophenyl, 4-tert-butylphenyl, 2,3-dimethylphenyl, 3- fluorophenyl, 3,4-difluorophenyl or 2-chloro-4-fluorophenyl; d) Y = O, Z is an unsubstituted saturated hydrocarbon chain having five carbon atoms, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl; e) Y = single bond to R1, Z is an unsubstituted hydrocarbon chain having two carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl or 4-chlorophenyl; f1 ) Y = single bond to R1, Z is an unsubstituted hydrocarbon chain having three carbon atoms, R2, R3 and R4 are hydrogen; and

R1 is as defined above or as defined above as being preferred, but not 4-chlorophenyl, 4-bromophenyl, 4-fluorophenyl or 4-methylphenyl; f2) Y = single bond to R1, Z is CH2CH(CH3)CH2, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 4-methylphenyl, 4-t-butylphenyl, 4-methoxyphenyl or 2,4-dichlorophenyl; g) Y = single bond to R1, Z is an unsubstituted hydrocarbon chain having four carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl or 4-chlorophenyl; hi ) Y = single bond to R1, Z is an unsubstituted hydrocarbon chain having five carbon atoms, R2, R3 and R4 are hydrogen, and

R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl, 4-chlorophenyl or 4-methylphenyl; h2) Y = single bond to R1, Z is a hydrocarbon chain which has five carbon atoms and is substituted by exactly one CH3 group, R2, R3 and R4 are hydrogen, and R1 is as defined above or as defined above as being preferred, but not unsubstituted phenyl. Mixtures according to the invention comprising one of the compounds 1-1 to 1-14 below are furthermore likewise specific embodiments of the invention. According to one aspect, the mixtures are binary mixtures. According to a further aspect, the mixtures are ternary or quaternary or higher mixtures. 1-1 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2-fluorophenyl and R2, R3 and R4 are hydrogen;

I-2 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2-chlorophenyl and R2, R3 and R4 are hydrogen;

I-3 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2,4-dichlorophenyl and R2, R3 and R4 are hydrogen;

I-4 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2,4-difluorophenyl and R2,

R3 and R4 is hydrogen;

I-5 formula I in which X = SH, Y = O, Z = (CH2)4, R1 = 2-fluorophenyl and R2, R3 and R4 are hydrogen;

I-6 formula I in which X = SH, Y = O, Z = (CH2)4, R1 = 2,4-difluorophenyl and

R2, R3 and R4 are hydrogen;

I-7 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R1

= 2,4-difluorophenyl and R2, R3 and R4 are hydrogen;

I-8 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R = 2-chloro-4-fluorophenyl and R2, R3 and R4 are hydrogen;

I-9 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R

= 2,4-dichlorophenyl and R2, R3 and R4 are hydrogen;

1-10 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R = 4-chloro-2-fluorophenyl and R2, R3 and R4 are hydrogen;

1-1 1 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R

= 2,4-dichlorophenyl and R2, R3 and R4 are hydrogen;

1-12 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R

= 4-chloro-2-fluorophenyl and R2, R3 and R4 are hydrogen;

1-13 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R = 2-chloro-4-fluorophenyl and R2, R3 and R4 are hydrogen; and

1-14 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R = 2,4-difluorophenyl and R2, R3 and R4 are hydrogen.

According to one embodiment of the present invention, the mixtures according to the invention comprise a compound selected from the group consisting of 1-1 , I-4, I-5, I-6, I- 9, 1-1 1 , 1-12, 1-13 and 1-14. According to one aspect, the mixtures are binary mixtures. According to a further aspect, the mixtures are ternary or quaternary or higher mixtures.

According to a further embodiment of the present invention, the mixtures according to the invention comprise a compound selected from the group consisting of 1-5, 1-6, 1-1 1 , 1-12, 1-13 and 1-14. According to one aspect, the mixtures are binary mixtures.

According to a further aspect, the mixtures are ternary or quaternary or higher mixtures. According to a further embodiment of the present invention, the mixtures according to the invention comprise a compound selected from the group consisting of 1-1 , I-5, I-9 and 1-1 1 , in particular I-5 and 1-1 1. According to one aspect, the mixtures are binary mixtures. According to a further aspect, the mixtures are ternary or quaternary or higher mixtures.

According to yet a further embodiment of the present invention, the mixtures according to the invention comprise a compound selected from the group consisting of 1-1 , I-4 and I-9. According to one aspect, the mixtures are binary mixtures. According to one aspect, the mixtures are ternary or quaternary or higher mixtures.

According to a further embodiment of the invention, the mixtures according to the invention comprise a compound I in the form of a pure enantiomer. According to a further subject matter of the invention, the mixtures according to the invention comprise a diastereomer (consisting of a pair of enantiomers) in the mixtures according to the invention, where the enantiomers may be in any ratio to one another, in particular as a racemic mixture (50:50).

According to a further embodiment of the invention, the mixtures according to the invention comprise a compound I in the form of a diastereomer mixture. It may be preferred for the compound I to be present in the form of a diastereomer mixture of two diastereomers. Two diastereomers may be present in any ratio to one another. Ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially of 1 :1 , may be particularly advantageous. From among the compounds of the formula I (1-1 to 1-14) specifically mentioned, it may be preferred that the following isomers are present in the mixtures according to the invention: l-5a 2-[(1 R)-5-(2-fluorophenoxy)-1 -[(1 S)-1 -hydroxy-2,2-dimethylpropyl]pentyl]-4H- 1 ,2,4-triazole-3-thione l-5b 2-[(1 S)-5-(2-fluorophenoxy)-1 -[(1 R)-1 -hydroxy-2,2-dimethylpropyl]pentyl]-4H-

1 ,2,4-triazole3-thione

l-5c 2-[(1 R)-5-(2-fluorophenoxy)-1 -[(1 R)-1 -hydroxy-2,2-dimethylpropyl]pentyl]-4H-

1 ,2,4-triazole-3-thione

l-5d 2-[(1 S)-5-(2-fluorophenoxy)-1 -[(1 S)-1 -hydroxy-2,2-dimethylpropyl]pentyl]-4H- 1 ,2,4-triazole-3-thione

According to one aspect, the isomers l-5a, l-5b, l-5c, l-5d are present individually or as a mixture, in particular as mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially of 1 :1.

According to a further aspect, the isomers l-5a and l-5b are present individually or as a mixture, in particular in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially of 1 :1.

1-1 1 a 2-[(1 S,2S)-1 -[(2S)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 b 2-[(1 S,2S)-1 -[(2R)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 c 2-[(1 R,2R)-1 -[(2R)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3- dimethylbutyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 d 2-[(1 R,2R)-1 -[(2S)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 e 2-[(1 S,2R)-1 -[(2S)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 f 2-[(1 S,2R)-1 -[(R)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 g 2-[(1 R,2S)-1 -[(2R)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

1-1 1 h 2-[(1 R,2S)-1 -[(2S)-3-(2,4-dichlorophenyl)-2-methylpropyl]-2-hydroxy-3,3-dimethyl- butyl]-4H-1 ,2,4-triazole-3-thione

According to one aspect, the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are present in each case individually or as a mixture, in particular as mixture of the two diastereomers

(which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially of 1 :1.

Components 2), 3) and 4) (or further components) are independently of one another preferably selected as illustrated in the compositions below. Here, component 1 ) in the mixtures is in each case independently selected from the compounds I, as defined herein or as defined as being preferred: Preference is given to compositions of a compound I (component 1 )) with at least one active compound from group A) (in particular component 2) and/or 3)) of the strobilurins and in particular selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin,

pyraclostrobin and trifloxystrobin. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group A) (component 2) and/or 3) and/or 4)) of the strobilurins, which are preferably selected from those just mentioned.According to one specific embodiment of the invention, preference is given to 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14, and, as component 2, an active compound from the strobilurins, where component 2 is selected in particular from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin,

picoxystrobin, pyraclostrobin and trifloxystrobin. According to a specific aspect, these are binary mixtures which, as active compounds, comprise in each case only the two components. According to a further aspect, these mixtures comprise a further component (component 3) selected from carboxamides, in particular selected from the group consisting of bixafen, boscalid, fluopyram, isopyrazam, penthiopyrad, sedaxane, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide and penflufen.

Preference is also given to compositions of a compound I (component 1 )) with at least one active compound selected from group B) (in particular component 2) and/or 3)) of the carboxamides and particularly preferably selected from the group consisting of bixafen, boscalid, isopyrazam, fluopyram, penflufen, penthiopyrad, sedaxane, fenhexamid, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamid), zoxamide, carpropamid, mandipropamid and N-(3',4',5'-trifluorobi- phenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group B) (component 2) and/or 3) and/or 4)) of the

carboxamides, which are preferably selected from those just mentioned. According to a specific embodiment of the invention, the compound I (component I) 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

Preference is also given to compositions of a compound I (component 1 )) with at least one active compound selected from group C) (in particular component 2) and/or 3)) of the azoles and in particular selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group C) (component 2) and/or 3) and/or 4)) of the azoles, which are preferably selected from those just mentioned. According to a specific embodiment of the invention, the compound I (component I) 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

Preference is also given to compositions of a compound I (component 1 )) with at least one active compound selected from group D) (in particular component 2) and/or 3)) of the nitrogenous heterocyclyl compounds and in particular selected from the group consisting of fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group D) (component 2) and/or 3) and/or 4)) of the nitrogenous heterocyclyl compounds, which are preferably selected from those just mentioned. According to a specific embodiment of the invention, the compound I (component I) 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. Preference is also given to compositions of a compound I (component 1 )) with at least one active compound selected from group E) (in particular component 2) and/or 3)) of the carbamates and in particular selected from the group consisting of mancozeb, metiram, propineb, thiram, iprovalicarb, benthiavalicarb and propamocarb. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group E) (component 2) and/or 3) and/or 4)) of the carbamates, which are preferably selected from those just mentioned. According to a specific embodiment of the invention, the compound I (component I) 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

Preference is also given to compositions of a compound I (component 1 )) with at least one active compound selected from the fungicides of group F) (in particular component 2) and/or 3)) and in particular selected from the group consisting of dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and salts thereof, 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-1 H-pyrazol-1 - yl)acetyl]piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thi- azolecarboxamide. Specific quaternary compositions of the invention comprise a compound I (component 1 )) and at least one active compound from group F)

(component 2) and/or 3) and/or 4)), which are preferably selected from those just mentioned. According to a specific embodiment of the invention, the compound I (component I) 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to one embodiment, the compositions according to the invention comprise a compound I (component 1 ), and a component 2, component 2 being a growth regulator. Component 2 is selected in particular from the group consisting of chlormequat (chlormequat chloride), mepiquat (mepiquat chloride), metconazole, paclobutrazole, prohexadione (prohexadione-calcium), trinexapac-ethyl and

uniconazole. According to one 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to a further embodiment, the compositions according to the invention comprise a compound I (component 1 ), and a component 2, component 2 being an insecticide. According to a preferred embodiment, these are binary mixtures

comprising, as active compounds, a component 1 ) and a component 2) selected from the group of insecticides. 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to one aspect, the insecticide of component 2) is selected from the group of the organo(thio)phosphates, in particular selected from the group consisting of acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl-parathion, monocrotophos, phorate, profenofos and terbufos. According to a specific embodiment of the invention, 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to a further aspect, the insecticide of component 2) is selected from the group of the carbamates, in particular selected from the group consisting of 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 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. According to yet a further aspect, the insecticide of component 2) is selected from the group of the pyrethroids, in particular selected from the group consisting of: bifenthrin, cyfluthrin, beta-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 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. According to yet a further aspect, the insecticide of component 2) is selected from the group of inhibitors of insect growth, in particular selected from the group consisting of lufenuron and spirotetramat. 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to yet a further aspect, the insecticide of component 2) is selected from the group of the nicotine receptor agonists/antagonists, in particular selected from the group consisting of: clothianidin, imidacloprid, thiamethoxam and thiacloprid. According to a specific embodiment of the invention, 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, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to yet a further aspect, the insecticide of component 2) is selected from the group of the GABA antagonists, in particular selected from the group consisting of: endosulfan and fipronil. 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. According to yet a further aspect, the insecticide of component 2) is selected from the group of the macrocyclic lactones, in particular selected from the group consisting of: 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 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to yet a further aspect, the insecticide of component 2) is hydramethylnon. 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, I-8, I-9, 1-10, I- 1 1 , 1-12, 1-13 and 1-14.

According to yet a further aspect, 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 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, I- 1 1 , 1-12, 1-13 and 1-14.

According to yet a further aspect, the insecticide of component 2) is selected from the group consisting of 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 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

According to a further embodiment, the mixtures are ternary mixtures comprising, in addition to the components mentioned, a component 3) selected from the active compounds II of the group of insecticides mentioned above. 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. According to a further embodiment, the mixtures are ternary mixtures comprising, in addition to the two components mentioned, a component 3) selected from the active compounds II of groups A) to G). According to one 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14.

The active compounds II of the group of insecticides and their pesticidal action and processes for their preparation are known (see also

httpi/'/www.hclrss. demon.co.uk/index.html). Commercially available active compounds can be found, for example, in The Pesticide Manual, 14th Edition, British Crop

Protection Council (2006) and other publications. The compound BB)

Figure imgf000039_0001

having the lUPAC name

[(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 cyclopropanecarboxylate and its pesticidal action are disclosed in WO2006/129714 and WO2009/081851 .

In a preferred embodiment, component 2 is a fungicide selected from groups A to F. If a component 3 is present, this is, in another preferred embodiment, an independently selected compound II selected from groups A to I. In a further preferred embodiment, components 2 and 3 are selected from groups A to F. If a component 4 is present, this is, in another preferred embodiment, an independently selected from groups A to I. In a further preferred embodiment, components 2, 3 and 4 are three fungicides

independently selected from groups A to I. 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, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13 and 1-14. In compositions according to the invention comprising, in addition to a compound I (component 1 )), the components 2), 3) and 4) , the components 2) and 3) are independently preferably selected as described above as preferred for the components 2) and 3), and component 4) is likewise preferably selected as described for

components 2) and 3). Altogether, the components present in the compositions according to the invention are different from one another.

Particularly preferred components 2) are compounds II selected from the group of the following compounds:

11-1 epoxiconazole 35 II-23 bixafen

II-2 metconazole II-24 boscalid

II-3 tebuconazole II-25 N-(3',4\5'-trifluorobiphenyl-

II-4 fluquinconazole 2-yl)-3-difluoromethyl-1 -

II-5 flutriafol methyl-1 H-pyrazole-4-

II-6 triticonazole 40 carboxamide (Fluxapyroxad)

II-7 prothioconazole II-26 sedaxane

11—3 kresoxim-methyl II-27 isopyrazam

II-9 pyraclostrobin II-28 fluopyram

11-10 orysastrobin II-29 penflufen

11-1 1 dimethomorph 45 II-30 cyflufenamid

11-12 5-ethyl-6-octyl- 11-31 spiroxamine

[1 ,2,4]triazolo[1 ,5- II-32 fenpropidin

a]pyrimidin-7-ylamine II-33 proquinazid

(Ametoctradine) II-34 dimoxystrobin

11-13 pyrimethanil 50 II-35 iprovalicarb

11-14 metalaxyl II-36 folpet

11-15 fenpropimorph II-37 prochloraz

11-16 dodemorph II-38 dithianon

11-17 iprodione II-39 difenoconazole

11-18 mancozeb 55 II-40 azoxystrobin

11-19 metiram 11-41 trifloxystrobin

II-20 thiophanate methyl II-42 penthiopyrad

11-21 chlorothalonil II-43 picoxystrobin

II-22 metrafenone II-44 fluoxastrobin

Particularly preferred mixtures are the binary mixtures of Table B, where each row corresponds to one aspect of the mixtures according to the invention. According to one aspect, the active compounds of the formula I are present in the form of a pure enantiomer. According to a further subject matter of the invention, the mixtures according to the invention comprise a diastereomer (consiting of a pair of enantiomers), where the enantiomers may be present in any ratio to one another, in particular as a racemic mixture (50:50). According to a further embodiment of the invention, the mixtures according to the invention of Table B comprise a compound I in the form of a mixture of diastereomers. It may be preferred for the compound I to be present in the form of a diastereomer mixture of two diastereomers. Two diastereomers may be present in any ratio to one another. Ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially 1 :1 , may be particularly advantageous. The mixture comprises in particular the compounds I-5 and 1-1 1 in the isomer ratios mentioned above.

Table B: Binary mixtures comprising one component 1 ) selected from compounds of the formula I and one component 2) selected from groups A to I

Mixture 1) 2) Mixture 1) 2)

B-1 1-1 11-1 B-30 I-2 11-1

B-2 1-1 II-2 B-31 I-2 II-2

B-3 1-1 II-3 B-32 I-2 II-3

B-4 1-1 II-30 B-33 I-2 II-30

B-5 1-1 11-31 B-34 I-2 11-31

B-6 1-1 II-6 B-35 I-2 II-6

B-7 1-1 II-7 B-36 I-2 II-7

B-8 1-1 II-8 B-37 I-2 II-8

B-9 1-1 II-9 B-38 I-2 II-9

B-10 1-1 11-10 B-39 I-2 11-10

B-1 1 1-1 11-1 1 B-40 I-2 11-1 1

B-12 1-1 11-12 B-41 I-2 11-12

B-13 1-1 11-13 B-42 I-2 11-13

B-14 1-1 11-14 B-43 I-2 11-14

B-15 1-1 11-15 B-44 I-2 11-15

B-16 1-1 11-16 B-45 I-2 11-16

B-17 1-1 11-17 B-46 I-2 11-17

B-18 1-1 11-18 B-47 I-2 11-18

B-19 1-1 11-19 B-48 I-2 11-19

B-20 1-1 II-20 B-49 I-2 II-20

B-21 1-1 11-21 B-50 I-2 11-21

B-22 1-1 II-22 B-51 I-2 II-22

B-23 1-1 II-23 B-52 I-2 II-23

B-24 1-1 II-24 B-53 I-2 II-24

B-25 1-1 II-25 B-54 I-2 II-25

B-26 1-1 II-26 B-55 I-2 II-26

B-27 1-1 II-27 B-56 I-2 II-27

B-28 1-1 II-28 B-57 I-2 II-28

B-29 1-1 II-29 B-58 I-2 II-29 Mixture 1) 2) Mixture 1) 2)

B-59 I-3 11-1 B-100 I-4 11-13

B-60 I-3 II-2 B-101 I-4 11-14

B-61 I-3 II-3 B-102 I-4 11-15

B-62 I-3 II-30 B-103 I-4 11-16

B-63 I-3 11-31 B-104 I-4 11-17

B-64 I-3 II-6 B-105 I-4 11-18

B-65 I-3 II-7 B-106 I-4 11-19

B-66 I-3 II-8 B-107 I-4 II-20

B-67 I-3 II-9 B-108 I-4 11-21

B-68 I-3 11-10 B-109 I-4 II-22

B-69 I-3 11-1 1 B-1 10 I-4 II-23

B-70 I-3 11-12 B-1 1 1 I-4 II-24

B-71 I-3 11-13 B-1 12 I-4 II-25

B-72 I-3 11-14 B-1 13 I-4 II-26

B-73 I-3 11-15 B-1 14 I-4 II-27

B-74 I-3 11-16 B-1 15 I-4 II-28

B-75 I-3 11-17 B-1 16 I-4 II-29

B-76 I-3 11-18 B-1 17 I-5 11-1

B-77 I-3 11-19 B-1 18 I-5 II-2

B-78 I-3 II-20 B-1 19 I-5 II-3

B-79 I-3 11-21 B-120 I-5 II-30

B-80 I-3 II-22 B-121 I-5 11-31

B-81 I-3 II-23 B-122 I-5 II-6

B-82 I-3 II-24 B-123 I-5 II-7

B-83 I-3 II-25 B-124 I-5 II-8

B-84 I-3 II-26 B-125 I-5 II-9

B-85 I-3 II-27 B-126 I-5 11-10

B-86 I-3 II-28 B-127 I-5 11-1 1

B-87 I-3 II-29 B-128 I-5 11-12

B-88 I-4 11-1 B-129 I-5 11-13

B-89 I-4 II-2 B-130 I-5 11-14

B-90 I-4 II-3 B-131 I-5 11-15

B-91 I-4 II-30 B-132 I-5 11-16

B-92 I-4 11-31 B-133 I-5 11-17

B-93 I-4 II-6 B-134 I-5 11-18

B-94 I-4 II-7 B-135 I-5 11-19

B-95 I-4 II-8 B-136 I-5 II-20

B-96 I-4 II-9 B-137 I-5 11-21

B-97 I-4 11-10 B-138 I-5 II-22

B-98 I-4 11-1 1 B-139 I-5 II-23

B-99 I-4 11-12 B-140 I-5 II-24 Mixture 1) 2) Mixture 1) 2)

B-141 I-5 II-25 B-182 I-9 II-8

B-142 I-5 II-26 B-183 I-9 II-9

B-143 I-5 II-27 B-184 I-9 11-10

B-144 I-5 II-28 B-185 I-9 11-1 1

B-145 I-5 II-29 B-186 I-9 11-12

B-146 I -7 11-1 B-187 I-9 11-13

B-147 I -7 II-2 B-188 I-9 11-14

B-148 I -7 II-3 B-189 I-9 11-15

B-149 I -7 II-30 B-190 I-9 11-16

B-150 I -7 11-31 B-191 I-9 11-17

B-151 I -7 II-6 B-192 I-9 11-18

B-152 I -7 II-7 B-193 I-9 11-19

B-153 I -7 II-8 B-194 I-9 II-20

B-154 I -7 II-9 B-195 I-9 11-21

B-155 I -7 11-10 B-196 I-9 II-22

B-156 I -7 11-1 1 B-197 I-9 II-23

B-157 I -7 11-12 B-198 I-9 II-24

B-158 I -7 11-13 B-199 I-9 II-25

B-159 I -7 11-14 B-200 I-9 II-26

B-160 I -7 11-15 B-201 I-9 II-27

B-161 I -7 11-16 B-202 I-9 II-28

B-162 I -7 11-17 B-203 I-9 II-29

B-163 I -7 11-18 B-204 1-1 1 11-1

B-164 I -7 11-19 B-205 1-1 1 II-2

B-165 I -7 II-20 B-206 1-1 1 II-3

B-166 I -7 11-21 B-207 1-1 1 II-30

B-167 I -7 II-22 B-208 1-1 1 11-31

B-168 I -7 II-23 B-209 1-1 1 II-6

B-169 I -7 II-24 B-210 1-1 1 II-7

B-170 I -7 II-25 B-21 1 1-1 1 II-8

B-171 I -7 II-26 B-212 1-1 1 II-9

B-172 I -7 II-27 B-213 1-1 1 11-10

B-173 I -7 II-28 B-214 1-1 1 11-1 1

B-174 I -7 II-29 B-215 1-1 1 11-12

B-175 I-9 11-1 B-216 1-1 1 11-13

B-176 I-9 II-2 B-217 1-1 1 11-14

B-177 I-9 II-3 B-218 1-1 1 11-15

B-178 I-9 II-30 B-219 1-1 1 11-16

B-179 I-9 11-31 B-220 1-1 1 11-17

B-180 I-9 II-6 B-221 1-1 1 11-18

B-181 I-9 II-7 B-222 1-1 1 11-19 Mixture 1) 2) Mixture 1) 2)

B-223 1-1 1 II-20 B-243 1-14 11-1 1

B-224 1-1 1 11-21 B-244 1-14 11-12

B-225 1-1 1 II-22 B-245 1-14 11-13

B-226 1-1 1 II-23 B-246 1-14 11-14

B-227 1-1 1 II-24 B-247 1-14 11-15

B-228 1-1 1 II-25 B-248 1-14 11-16

B-229 1-1 1 II-26 B-249 1-14 11-17

B-230 1-1 1 II-27 B-250 1-14 11-18

B-231 1-1 1 II-28 B-251 1-14 11-19

B-232 1-1 1 II-29 B-252 1-14 II-20

B-233 1-14 11-1 B-253 1-14 11-21

B-234 1-14 II-2 B-254 1-14 II-22

B-235 1-14 II-3 B-255 1-14 II-23

B-236 1-14 II-30 B-256 1-14 II-24

B-237 1-14 11-31 B-257 1-14 II-25

B-238 1-14 II-6 B-258 1-14 II-26

B-239 1-14 II-7 B-259 1-14 II-27

B-240 1-14 II-8 B-260 1-14 II-28

B-241 1-14 II-9 B-261 1-14 II-29

B-242 1-14 11-10

Mixture 1) 2) Mixture 1) 2)

B-262 1-1 II-32 B-281 I-2 II-38

B-263 1-1 II-33 B-282 I-2 II-39

B-264 1-1 II-34 B-283 I-2 II-40

B-265 1-1 II-35 B-284 I-2 11-41

B-266 1-1 II-36 B-285 I-2 II-42

B-267 1-1 II-37 B-286 I-2 II-43

B-268 1-1 II-38 B-287 I-2 II-44

B-269 1-1 II-39 B-288 I-3 II-32

B-270 1-1 II-40 B-289 I-3 II-33

B-271 1-1 11-41 B-290 I-3 II-34

B-272 1-1 II-42 B-291 I-3 II-35

B-273 1-1 II-43 B-292 I-3 II-36

B-274 1-1 II-44 B-293 I-3 II-37

B-275 I-2 II-32 B-294 I-3 II-38

B-276 I-2 II-33 B-295 I-3 II-39

B-277 I-2 II-34 B-296 I-3 II-40

B-278 I-2 II-35 B-297 I-3 11-41

B-279 I-2 II-36 B-298 I-3 II-42

B-280 I-2 II-37 B-299 I-3 II-43 Mixture 1) 2) Mixture 1) 2)

B-300 I-3 II-44 B-340 I-9 II-32

B-301 I-4 II-32 B-341 I-9 II-33

B-302 I-4 II-33 B-342 I-9 II-34

B-303 I-4 II-34 B-343 I-9 II-35

B-304 I-4 II-35 B-344 I-9 II-36

B-305 I-4 II-36 B-345 I-9 II-37

B-306 I-4 II-37 B-346 I-9 II-38

B-307 I-4 II-38 B-347 I-9 II-39

B-308 I-4 II-39 B-348 I-9 II-40

B-309 I-4 II-40 B-349 I-9 11-41

B-310 I-4 11-41 B-350 I-9 II-42

B-31 1 I-4 II-42 B-351 I-9 II-43

B-312 I-4 II-43 B-352 I-9 II-44

B-313 I-5 II-44 B-353 1-1 1 II-32

B-314 I-5 II-32 B-354 1-1 1 II-33

B-315 I-5 II-33 B-355 1-1 1 II-34

B-316 I-5 II-34 B-356 1-1 1 II-35

B-317 I-5 II-35 B-357 1-1 1 II-36

B-318 I-5 II-36 B-358 1-1 1 II-37

B-319 I-5 II-37 B-359 1-1 1 II-38

B-320 I-5 II-38 B-360 1-1 1 II-39

B-321 I-5 II-39 B-361 1-1 1 II-40

B-322 I-5 II-40 B-362 1-1 1 11-41

B-323 I-5 11-41 B-363 1-1 1 II-42

B-324 I-5 II-42 B-364 1-1 1 II-43

B-325 I-5 II-43 B-365 1-1 1 II-44

B-326 I-5 II-44 B-366 1-14 II-32

B-327 I -7 II-32 B-367 1-14 II-33

B-328 I -7 II-33 B-368 1-14 II-34

B-329 I -7 II-34 B-369 1-14 II-35

B-330 I -7 II-35 B-370 1-14 II-36

B-331 I -7 II-36 B-371 1-14 II-37

B-332 I -7 II-37 B-372 1-14 II-38

B-333 I -7 II-38 B-373 1-14 II-39

B-334 I -7 II-39 B-374 1-14 II-40

B-335 I -7 II-40 B-375 1-14 11-41

B-336 I -7 11-41 B-376 1-14 II-42

B-337 I -7 II-42 B-377 1-14 II-43

B-338 I -7 II-43 B-378 1-14 II-44

B-339 I -7 II-44 Further preferred components 2 are compounds II selected from the group of the growth regulators G), in particular selected from the following compounds:

II-45 mepiquat chloride

II-46 chlormequat chloride

II-47 trinexapac-ethyl

II-48 prohexadione-calcium

Further preferred mixtures are the mixtures of Table B1 , where each row corresponds to one aspect of the mixtures according to the invention. According to a specific aspect, these are binary mixtures comprising, as active compounds, in each case only these two components.

Table B1 Mixtures comprising a component 1 selected from compounds of the formula I and a component 2 selected from group G)

Figure imgf000046_0002

15

Figure imgf000046_0001

According to a further embodiment, particularly preferred components 2 are

compounds II selected from the group I), in particular selected from the following compounds:

11-1 a acephate ll-15a pirimicarb

ll-2a chlorpyrifos ll-16a tefluthrin

ll-3a dimethoate 35 ll-17a spirotetramat ll-4a methamidophos ll-18a endosulfan

ll-5a terbufos ll-19a abamectin

ll-6a aldicarb ll-20a spinosad

ll-7a carbofuran 11-21 a spinetoram

ll-8a bifenthrin 40 ll-22a hydramethylnon ll-9a alpha-cypermethrin ll-23a fenbutatin oxide ll-10a deltamethrin ll-24a chlorfenapyr ll-1 1 a lambda-cyhalothrin ll-25a cyazypyr

ll-12a betacyfluthrin ll-26a cyflumetofen ll-13a zetacypermethrin 45 ll-27a flubendiamide ll-14a esfenvalerate ll-28a indoxacarb ll-29a metaflumizon 10 oxo-9-(pyridin-3-yl)- ll-30a fipronil 1 ,2,3,4,4a,5,6,6a,12a, 11-31 a 12b-decahydro-

[(3S,4R,4aR,6S, 1 1 H.12H-

6aS,12R,12aS,12bS)- benzo[f]pyrano[4,3-

3- 15 b]chromen-4-yl]methyl

(cyclopropanecarbony cyclopropanecarboxyl loxy)-6 , 12-d i hyd roxy- ate.

4,6a,12b-trimethyl-1 1 - Particularly preferred mixtures are the mixtures of Table B2, where each row

corresponds to one aspect of the mixtures according to the invention. According to a specific aspect, these are binary mixtures comprising, as active compounds, in each case only these two components.

Table B2: Mixtures comprising a component 1 selected from preferred compounds of the formula I and a component 2 selected from group I)

Component Component

Mixture 1 2 Mixture 1 2

B2-1 1-1 11-1 a B2-31 1-1 11-31 a

B2-2 1-1 ll-2a B2-32 I-5 11-1 a

B2-3 1-1 ll-3a B2-33 I-5 ll-2a

B2-4 1-1 ll-4a B2-34 I-5 ll-3a

B2-5 1-1 ll-5a B2-35 I-5 ll-4a

B2-6 1-1 ll-6a B2-36 I-5 ll-5a

B2-7 1-1 ll-7a B2-37 I-5 ll-6a

B2-8 1-1 ll-8a B2-38 I-5 ll-7a

B2-9 1-1 ll-9a B2-39 I-5 ll-8a

B2-10 1-1 11-10a B2-40 I-5 ll-9a

B2-1 1 1-1 11- a B2-41 I-5 11-10a

B2-12 1-1 ll-12a B2-42 I-5 11- a

B2-13 1-1 11-13a B2-43 I-5 ll-12a

B2-14 1-1 ll-14a B2-44 I-5 11-13a

B2-15 1-1 11-15a B2-45 I-5 ll-14a

B2-16 1-1 11-16a B2-46 I-5 11-15a

B2-17 1-1 11-17a B2-47 I-5 11-16a

B2-18 1-1 11-18a B2-48 I-5 11-17a

B2-19 1-1 11-19a B2-49 I-5 11-18a

B2-20 1-1 ll-20a B2-50 I-5 11-19a

B2-21 1-1 11-21 a B2-51 I-5 ll-20a

B2-22 1-1 ll-22a B2-52 I-5 11-21 a

B2-23 1-1 ll-23a B2-53 I-5 ll-22a

B2-24 1-1 ll-24a B2-54 I-5 ll-23a

B2-25 1-1 ll-25a B2-55 I-5 ll-24a

B2-26 1-1 ll-26a B2-56 I-5 ll-25a

B2-27 1-1 ll-27a B2-57 I-5 ll-26a

B2-28 1-1 ll-28a B2-58 I-5 ll-27a

B2-29 1-1 ll-29a B2-59 I-5 ll-28a

B2-30 1-1 ll-30a B2-60 I-5 ll-29a Component Component

Mixture 1 2 Mixture 1 2

B2-61 I-5 ll-30a B2-94 1-11 11-1 a

B2-62 I-5 11-31 a B2-95 1-11 ll-2a

B2-63 I-9 11-1 a B2-96 1-11 ll-3a

B2-64 I-9 ll-2a B2-97 1-11 ll-4a

B2-65 I-9 ll-3a B2-98 1-11 ll-5a

B2-66 I-9 ll-4a B2-99 1-11 ll-6a

B2-67 I-9 ll-5a B2-100 1-11 ll-7a

B2-68 I-9 ll-6a B2-101 1-11 ll-8a

B2-69 I-9 ll-7a B2-102 1-11 ll-9a

B2-70 I-9 ll-8a B2-103 1-11 11-10a

B2-71 I-9 ll-9a B2-104 1-11 11-11 a

B2-72 I-9 11-10a B2-105 1-11 ll-12a

B2-73 I-9 11- a B2-106 1-11 11-13a

B2-74 I-9 ll-12a B2-107 1-11 ll-14a

B2-75 I-9 11-13a B2-108 1-11 11-15a

B2-76 I-9 ll-14a B2-109 1-11 11-16a

B2-77 I-9 11-15a B2-110 1-11 11-17a

B2-78 I-9 11-16a B2-111 1-11 11-18a

B2-79 I-9 11-17a B2-112 1-11 11-19a

B2-80 I-9 11-18a B2-113 1-11 ll-20a

B2-81 I-9 11-19a B2-114 1-11 11-21 a

B2-82 I-9 ll-20a B2-115 1-11 ll-22a

B2-83 I-9 11-21 a B2-116 1-11 ll-23a

B2-84 I-9 ll-22a B2-117 1-11 ll-24a

B2-85 I-9 ll-23a B2-118 1-11 ll-25a

B2-86 I-9 ll-24a B2-119 1-11 ll-26a

B2-87 I-9 ll-25a B2-120 1-11 ll-27a

B2-88 I-9 ll-26a B2-121 1-11 ll-28a

B2-89 I-9 ll-27a B2-122 1-11 ll-29a

B2-90 I-9 ll-28a B2-123 1-11 ll-30a

B2-91 I-9 ll-29a B2-124 1-11 11-31 a

B2-92 I-9 ll-30a

B2-93 I-9 11-31 a

According to a further embodiment, particularly preferred components 2 are compounds II selected from the group of the following compounds:

-32a clothianidin

-33a dinotefuran

-34a imidacloprid

-35a thiamethoxam

-36a nitenpyram

-37a acetamiprid

-38a thiacloprid

Particularly preferred mixtures are the mixtures of Table B3, where each row corresponds to one aspect of the mixtures according to the invention. According to a specific aspect, these are binary mixtures comprising, as active compounds, in each case only these two components. Table B3: Mixtures comprising a component 1 selected from preferred compounds of the formula I and a component 2 selected from group I)

Figure imgf000049_0001
Figure imgf000049_0002

According to a further embodiment, particularly preferred components 2 are compounds II selected from the active compounds of group H). With special preference, the active compounds according to this embodiment are selected from the group of the following compounds of group H):

11-1 b glyphosate

ll-2b imazamox

Particularly preferred mixtures are the mixtures of Table B4, where each row corresponds to one aspect of the mixtures according to the invention. According to a specific aspect, these are binary mixtures comprising, as active compounds, in each case only these two components.

Table B4: Mixtures comprising a component 1 selected from preferred compounds of the formula I and a component 2 selected from group H)

Figure imgf000049_0003
Figure imgf000049_0004
Particularly preferred components 3) are compounds II selected from the group of the following compounds:

II-2 metconazole

11-1 epoxiconazole 11-3 tebuconazole II-23 bixafen

11-6 triticonazole II-24 boscalid

11-7 prothioconazole 20 II-25 N-(3',4',5'-trifluorobiphenyl

11-8 kresoxim-methyl 2-yl)-3-difluoromethyl-1 -

11-9 pyraclostrobin methyl-1 H-pyrazole-4-

11-1 1 dimethomorph carboxamide

11-12 5-ethyl-6-octyl- II-26 sedaxane

[1 ,2,4]triazolo[1 ,5- 25 II-27 isopyrazam

a]pyrimidin-7-ylamine II-28 fluopyram

11-13 pyrimethanil II-29 penflufen

11-14 metalaxyl II-30 cyflufenamid

11-15 fenpropimorph II-34 dimoxystrobin

11-18 mancozeb 30 II-37 prochloraz

11-19 metiram II-39 difenoconazole

II-20 thiophanate methyl II-40 azoxystrobin

11-21 chlorothalonil

II-22 metrafenone with the proviso that component 2) and component 3) are not identical.

Particularly preferred mixtures are the ternary mixtures of Table T, where each row corresponds to one aspect of the mixtures according to the invention. According to one aspect, the active compounds of the formula I are present in the form of a pure enantiomer. According to a further subject matter of the invention, the mixtures according to the invention comprise a diastereomer (consisting of a pair of

enantiomers), where the enantiomers may be present in any ratio to one another, in particular as a racemic mixture (50:50). According to a further embodiment of the invention, the mixtures according to the invention of Table B comprise a compound I in the form of a mixture of diastereomers. It may be preferred for the compound I to be present in the form of a diastereomer mixture of two diastereomers. Two diastereomers may be present in any ratio to one another. Ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially 1 :1 , may be particularly advantageous. The mixture comprises in particular the compounds I-5 and 1-1 1 in the isomer ratios mentioned above. In the table below, each row of a mixture according to the invention corresponds to each mixture component 1 to 3 given in the corresponding row. "C" denotes "component".Table T: Ternary mixtures comprising one component 1 ) selected from the compounds of the formula I, one component 2) selected from groups A to I and one component 3) selected from groups A to I

Mixture C1 C2 C3 Mixture C1 C2 C3

T-1 1-1 11-1 II-2 T-5 1-1 11-1 II-8

T-2 1-1 11-1 II-3 T-6 1-1 11-1 II-9

T-3 1-1 11-1 II-6 T-7 1-1 11-1 11-1 1

T-4 1-1 11-1 II-7 T-8 1-1 11-1 11-12 Mixture C1 C2 C3 Mixture C1 C2 C3

T-9 1-1 11-1 11-13 T-50 1-1 II-3 11-11

T-10 1-1 11-1 11-14 T-51 1-1 II-3 11-12

T-11 1-1 11-1 11-15 T-52 1-1 II-3 11-13

T-12 1-1 11-1 11-18 T-53 1-1 II-3 11-14

T-13 1-1 11-1 11-19 T-54 1-1 II-3 11-15

T-14 1-1 11-1 II-20 T-55 1-1 II-3 11-18

T-15 1-1 11-1 11-21 T-56 1-1 II-3 11-19

T-16 1-1 11-1 II-22 T-57 1-1 II-3 II-20

T-17 1-1 11-1 II-23 T-58 1-1 II-3 11-21

T-18 1-1 11-1 II-24 T-59 1-1 II-3 II-22

T-19 1-1 11-1 II-25 T-60 1-1 II-3 II-23

T-20 1-1 11-1 II-26 T-61 1-1 II-3 II-24

T-21 1-1 11-1 II-27 T-62 1-1 II-3 II-25

T-22 1-1 11-1 II-28 T-63 1-1 II-3 II-26

T-23 1-1 11-1 II-29 T-64 1-1 II-3 II-27

T-24 1-1 II-2 II-3 T-65 1-1 II-3 II-28

T-25 1-1 II-2 II-6 T-66 1-1 II-3 II-29

T-26 1-1 II-2 II-7 T-67 1-1 II-4 11-1

T-27 1-1 II-2 II-8 T-68 1-1 II-4 II-2

T-28 1-1 II-2 II-9 T-69 1-1 II-4 II-3

T-29 1-1 II-2 11-11 T-70 1-1 II-4 II-6

T-30 1-1 II-2 11-12 T-71 1-1 II-4 II-7

T-31 1-1 II-2 11-13 T-72 1-1 II-4 II-8

T-32 1-1 II-2 11-14 T-73 1-1 II-4 II-9

T-33 1-1 II-2 11-15 T-74 1-1 II-4 11-11

T-34 1-1 II-2 11-18 T-75 1-1 II-4 11-12

T-35 1-1 II-2 11-19 T-76 1-1 II-4 11-13

T-36 1-1 II-2 II-20 T-77 1-1 II-4 11-14

T-37 1-1 II-2 11-21 T-78 1-1 II-4 11-15

T-38 1-1 II-2 II-22 T-79 1-1 II-4 11-18

T-39 1-1 II-2 II-23 T-80 1-1 II-4 11-19

T-40 1-1 II-2 II-24 T-81 1-1 II-4 II-20

T-41 1-1 II-2 II-25 T-82 1-1 II-4 11-21

T-42 1-1 II-2 II-26 T-83 1-1 II-4 II-22

T-43 1-1 II-2 II-27 T-84 1-1 II-4 II-23

T-44 1-1 II-2 II-28 T-85 1-1 II-4 II-24

T-45 1-1 II-2 II-29 T-86 1-1 II-4 II-25

T-46 1-1 II-3 II-6 T-87 1-1 II-4 II-26

T-47 1-1 II-3 II-7 T-88 1-1 II-4 II-27

T-48 1-1 II-3 II-8 T-89 1-1 II-4 II-28

T-49 1-1 II-3 II-9 T-90 1-1 II-4 II-29 Mixture C1 C2 C3 Mixture C1 C2 C3

T-91 1-1 II-5 11-1 T-132 1-1 II-6 II-27

T-92 1-1 II-5 II-2 T-133 1-1 II-6 II-28

T-93 1-1 II-5 II-3 T-134 1-1 II-6 II-29

T-94 1-1 II-5 II-6 T-135 1-1 II-7 II-8

T-95 1-1 II-5 II-7 T-136 1-1 II-7 II-9

T-96 1-1 II-5 II-8 T-137 1-1 II-7 11-11

T-97 1-1 II-5 II-9 T-138 1-1 II-7 11-12

T-98 1-1 II-5 11-11 T-139 1-1 II-7 11-13

T-99 1-1 II-5 11-12 T-140 1-1 II-7 11-14

T-100 1-1 II-5 11-13 T-141 1-1 II-7 11-15

T-101 1-1 II-5 11-14 T-142 1-1 II-7 11-18

T-102 1-1 II-5 11-15 T-143 1-1 II-7 11-19

T-103 1-1 II-5 11-18 T-144 1-1 II-7 II-20

T-104 1-1 II-5 11-19 T-145 1-1 II-7 11-21

T-105 1-1 II-5 II-20 T-146 1-1 II-7 II-22

T-106 1-1 II-5 11-21 T-147 1-1 II-7 II-23

T-107 1-1 II-5 II-22 T-148 1-1 II-7 II-24

T-108 1-1 II-5 II-23 T-149 1-1 II-7 II-25

T-109 1-1 II-5 II-24 T-150 1-1 II-7 II-26

T-110 1-1 II-5 II-25 T-151 1-1 II-7 II-27

T-111 1-1 II-5 II-26 T-152 1-1 II-7 II-28

T-112 1-1 II-5 II-27 T-153 1-1 II-7 II-29

T-113 1-1 II-5 II-28 T-154 1-1 II-8 II-9

T-114 1-1 II-5 II-29 T-155 1-1 II-8 11-11

T-115 1-1 II-6 II-7 T-156 1-1 II-8 11-12

T-116 1-1 II-6 II-8 T-157 1-1 II-8 11-13

T-117 1-1 II-6 II-9 T-158 1-1 II-8 11-14

T-118 1-1 II-6 11-11 T-159 1-1 II-8 11-15

T-119 1-1 II-6 11-12 T-160 1-1 II-8 11-18

T-120 1-1 II-6 11-13 T-161 1-1 II-8 11-19

T-121 1-1 II-6 11-14 T-162 1-1 II-8 II-20

T-122 1-1 II-6 11-15 T-163 1-1 II-8 11-21

T-123 1-1 II-6 11-18 T-164 1-1 II-8 II-22

T-124 1-1 II-6 11-19 T-165 1-1 II-8 II-23

T-125 1-1 II-6 II-20 T-166 1-1 II-8 II-24

T-126 1-1 II-6 11-21 T-167 1-1 II-8 II-25

T-127 1-1 II-6 II-22 T-168 1-1 II-8 II-26

T-128 1-1 II-6 II-23 T-169 1-1 II-8 II-27

T-129 1-1 II-6 II-24 T-170 1-1 II-8 II-28

T-130 1-1 II-6 II-25 T-171 1-1 II-8 II-29

T-131 1-1 II-6 II-26 T-172 1-1 II-9 11-11 Mixture C1 C2 C3 Mixture C1 C2 C3

T-173 1-1 II-9 11-12 T-214 1-1 11-11 11-13

T-174 1-1 II-9 11-13 T-215 1-1 11-11 11-14

T-175 1-1 II-9 11-14 T-216 1-1 11-11 11-15

T-176 1-1 II-9 11-15 T-217 1-1 11-11 11-18

T-177 1-1 II-9 11-18 T-218 1-1 11-11 11-19

T-178 1-1 II-9 11-19 T-219 1-1 11-11 II-20

T-179 1-1 II-9 II-20 T-220 1-1 11-11 11-21

T-180 1-1 II-9 11-21 T-221 1-1 11-11 II-22

T-181 1-1 II-9 II-22 T-222 1-1 11-11 II-23

T-182 1-1 II-9 II-23 T-223 1-1 11-11 II-24

T-183 1-1 II-9 II-24 T-224 1-1 11-11 II-25

T-184 1-1 II-9 II-25 T-225 1-1 11-11 II-26

T-185 1-1 II-9 II-26 T-226 1-1 11-11 II-27

T-186 1-1 II-9 II-27 T-227 1-1 11-11 II-28

T-187 1-1 II-9 II-28 T-228 1-1 11-11 II-29

T-188 1-1 II-9 II-29 T-229 1-1 11-12 11-13

T-189 1-1 11-10 11-1 T-230 1-1 11-12 11-14

T-190 1-1 11-10 II-2 T-231 1-1 11-12 11-15

T-191 1-1 11-10 II-3 T-232 1-1 11-12 11-18

T-192 1-1 11-10 II-6 T-233 1-1 11-12 11-19

T-193 1-1 11-10 II-7 T-234 1-1 11-12 II-20

T-194 1-1 11-10 II-8 T-235 1-1 11-12 11-21

T-195 1-1 11-10 II-9 T-236 1-1 11-12 II-22

T-196 1-1 11-10 11-11 T-237 1-1 11-12 II-23

T-197 1-1 11-10 11-12 T-238 1-1 11-12 II-24

T-198 1-1 11-10 11-13 T-239 1-1 11-12 II-25

T-199 1-1 11-10 11-14 T-240 1-1 11-12 II-26

T-200 1-1 11-10 11-15 T-241 1-1 11-12 II-27

T-201 1-1 11-10 11-18 T-242 1-1 11-12 II-28

T-202 1-1 11-10 11-19 T-243 1-1 11-12 II-29

T-203 1-1 11-10 II-20 T-244 1-1 11-13 11-14

T-204 1-1 11-10 11-21 T-245 1-1 11-13 11-15

T-205 1-1 11-10 II-22 T-246 1-1 11-13 11-18

T-206 1-1 11-10 II-23 T-247 1-1 11-13 11-19

T-207 1-1 11-10 II-24 T-248 1-1 11-13 II-20

T-208 1-1 11-10 II-25 T-249 1-1 11-13 11-21

T-209 1-1 11-10 II-26 T-250 1-1 11-13 II-22

T-210 1-1 11-10 II-27 T-251 1-1 11-13 II-23

T-211 1-1 11-10 II-28 T-252 1-1 11-13 II-24

T-212 1-1 11-10 II-29 T-253 1-1 11-13 II-25

T-213 1-1 11-11 11-12 T-254 1-1 11-13 II-26 Mixture C1 C2 C3 Mixture C1 C2 C3

T-255 1-1 11-13 II-27 T-296 1-1 11-16 11-19

T-256 1-1 11-13 II-28 T-297 1-1 11-16 II-20

T-257 1-1 11-13 II-29 T-298 1-1 11-16 11-21

T-258 1-1 11-14 11-15 T-299 1-1 11-16 II-22

T-259 1-1 11-14 11-18 T-300 1-1 11-16 II-23

T-260 1-1 11-14 11-19 T-301 1-1 11-16 II-24

T-261 1-1 11-14 II-20 T-302 1-1 11-16 II-25

T-262 1-1 11-14 11-21 T-303 1-1 11-16 II-26

T-263 1-1 11-14 II-22 T-304 1-1 11-16 II-27

T-264 1-1 11-14 II-23 T-305 1-1 11-16 II-28

T-265 1-1 11-14 II-24 T-306 1-1 11-16 II-29

T-266 1-1 11-14 II-25 T-307 1-1 11-17 11-1

T-267 1-1 11-14 II-26 T-308 1-1 11-17 II-2

T-268 1-1 11-14 II-27 T-309 1-1 11-17 II-3

T-269 1-1 11-14 II-28 T-310 1-1 11-17 II-6

T-270 1-1 11-14 II-29 T-311 1-1 11-17 II-7

T-271 1-1 11-15 11-18 T-312 1-1 11-17 II-8

T-272 1-1 11-15 11-19 T-313 1-1 11-17 II-9

T-273 1-1 11-15 II-20 T-314 1-1 11-17 11-11

T-274 1-1 11-15 11-21 T-315 1-1 11-17 11-12

T-275 1-1 11-15 II-22 T-316 1-1 11-17 11-13

T-276 1-1 11-15 II-23 T-317 1-1 11-17 11-14

T-277 1-1 11-15 II-24 T-318 1-1 11-17 11-15

T-278 1-1 11-15 II-25 T-319 1-1 11-17 11-18

T-279 1-1 11-15 II-26 T-320 1-1 11-17 11-19

T-280 1-1 11-15 II-27 T-321 1-1 11-17 II-20

T-281 1-1 11-15 II-28 T-322 1-1 11-17 11-21

T-282 1-1 11-15 II-29 T-323 1-1 11-17 II-22

T-283 1-1 11-16 11-1 T-324 1-1 11-17 II-23

T-284 1-1 11-16 II-2 T-325 1-1 11-17 II-24

T-285 1-1 11-16 II-3 T-326 1-1 11-17 II-25

T-286 1-1 11-16 II-6 T-327 1-1 11-17 II-26

T-287 1-1 11-16 II-7 T-328 1-1 11-17 II-27

T-288 1-1 11-16 II-8 T-329 1-1 11-17 II-28

T-289 1-1 11-16 II-9 T-330 1-1 11-17 II-29

T-290 1-1 11-16 11-11 T-331 1-1 11-18 11-19

T-291 1-1 11-16 11-12 T-332 1-1 11-18 II-20

T-292 1-1 11-16 11-13 T-333 1-1 11-18 11-21

T-293 1-1 11-16 11-14 T-334 1-1 11-18 II-22

T-294 1-1 11-16 11-15 T-335 1-1 11-18 II-23

T-295 1-1 11-16 11-18 T-336 1-1 11-18 II-24 Mixture C1 C2 C3 Mixture C1 C2 C3

T-337 1-1 11-18 II-25 T-378 1-1 II-23 II-26

T-338 1-1 11-18 II-26 T-379 1-1 II-23 II-27

T-339 1-1 11-18 II-27 T-380 1-1 II-23 II-28

T-340 1-1 11-18 II-28 T-381 1-1 II-23 II-29

T-341 1-1 11-18 II-29 T-382 1-1 II-24 II-25

T-342 1-1 11-19 II-20 T-383 1-1 II-24 II-26

T-343 1-1 11-19 11-21 T-384 1-1 II-24 II-27

T-344 1-1 11-19 II-22 T-385 1-1 II-24 II-28

T-345 1-1 11-19 II-23 T-386 1-1 II-24 II-29

T-346 1-1 11-19 II-24 T-387 1-1 II-25 II-26

T-347 1-1 11-19 II-25 T-388 1-1 II-25 II-27

T-348 1-1 11-19 II-26 T-389 1-1 II-25 II-28

T-349 1-1 11-19 II-27 T-390 1-1 II-25 II-29

T-350 1-1 11-19 II-28 T-391 1-1 II-26 II-27

T-351 1-1 11-19 II-29 T-392 1-1 II-26 II-28

T-352 1-1 II-20 11-21 T-393 1-1 II-26 II-29

T-353 1-1 II-20 II-22 T-394 1-1 II-27 II-28

T-354 1-1 II-20 II-23 T-395 1-1 II-27 II-29

T-355 1-1 II-20 II-24 T-396 1-1 II-28 II-29

T-356 1-1 II-20 II-25 T-397 I-5 11-1 II-2

T-357 1-1 II-20 II-26 T-398 I-5 11-1 II-3

T-358 1-1 II-20 II-27 T-399 I-5 11-1 II-6

T-359 1-1 II-20 II-28 T-400 I-5 11-1 II-7

T-360 1-1 II-20 II-29 T-401 I-5 11-1 II-8

T-361 1-1 11-21 II-22 T-402 I-5 11-1 II-9

T-362 1-1 11-21 II-23 T-403 I-5 11-1 11-11

T-363 1-1 11-21 II-24 T-404 I-5 11-1 11-12

T-364 1-1 11-21 II-25 T-405 I-5 11-1 11-13

T-365 1-1 11-21 II-26 T-406 I-5 11-1 11-14

T-366 1-1 11-21 II-27 T-407 I-5 11-1 11-15

T-367 1-1 11-21 II-28 T-408 I-5 11-1 11-18

T-368 1-1 11-21 II-29 T-409 I-5 11-1 11-19

T-369 1-1 II-22 II-23 T-410 I-5 11-1 II-20

T-370 1-1 II-22 II-24 T-411 I-5 11-1 11-21

T-371 1-1 II-22 II-25 T-412 I-5 11-1 II-22

T-372 1-1 II-22 II-26 T-413 I-5 11-1 II-23

T-373 1-1 II-22 II-27 T-414 I-5 11-1 II-24

T-374 1-1 II-22 II-28 T-415 I-5 11-1 II-25

T-375 1-1 II-22 II-29 T-416 I-5 11-1 II-26

T-376 1-1 II-23 II-24 T-417 I-5 11-1 II-27

T-377 1-1 II-23 II-25 T-418 I-5 11-1 II-28 Mixture C1 C2 C3 Mixture C1 C2 C3

T-419 I-5 11-1 II-29 T-460 I-5 II-3 II-27

T-420 I-5 II-2 II-3 T-461 I-5 II-3 II-28

T-421 I-5 II-2 II-6 T-462 I-5 II-3 II-29

T-422 I-5 II-2 II-7 T-463 I-5 II-4 11-1

T-423 I-5 II-2 II-8 T-464 I-5 II-4 II-2

T-424 I-5 II-2 II-9 T-465 I-5 II-4 II-3

T-425 I-5 II-2 11-11 T-466 I-5 II-4 II-6

T-426 I-5 II-2 11-12 T-467 I-5 II-4 II-7

T-427 I-5 II-2 11-13 T-468 I-5 II-4 II-8

T-428 I-5 II-2 11-14 T-469 I-5 II-4 II-9

T-429 I-5 II-2 11-15 T-470 I-5 II-4 11-11

T-430 I-5 II-2 11-18 T-471 I-5 II-4 11-12

T-431 I-5 II-2 11-19 T-472 I-5 II-4 11-13

T-432 I-5 II-2 II-20 T-473 I-5 II-4 11-14

T-433 I-5 II-2 11-21 T-474 I-5 II-4 11-15

T-434 I-5 II-2 II-22 T-475 I-5 II-4 11-18

T-435 I-5 II-2 II-23 T-476 I-5 II-4 11-19

T-436 I-5 II-2 II-24 T-477 I-5 II-4 II-20

T-437 I-5 II-2 II-25 T-478 I-5 II-4 11-21

T-438 I-5 II-2 II-26 T-479 I-5 II-4 II-22

T-439 I-5 II-2 II-27 T-480 I-5 II-4 II-23

T-440 I-5 II-2 II-28 T-481 I-5 II-4 II-24

T-441 I-5 II-2 II-29 T-482 I-5 II-4 II-25

T-442 I-5 II-3 II-6 T-483 I-5 II-4 II-26

T-443 I-5 II-3 II-7 T-484 I-5 II-4 II-27

T-444 I-5 II-3 II-8 T-485 I-5 II-4 II-28

T-445 I-5 II-3 II-9 T-486 I-5 II-4 II-29

T-446 I-5 II-3 11-11 T-487 I-5 II-5 11-1

T-447 I-5 II-3 11-12 T-488 I-5 II-5 II-2

T-448 I-5 II-3 11-13 T-489 I-5 II-5 II-3

T-449 I-5 II-3 11-14 T-490 I-5 II-5 II-6

T-450 I-5 II-3 11-15 T-491 I-5 II-5 II-7

T-451 I-5 II-3 11-18 T-492 I-5 II-5 II-8

T-452 I-5 II-3 11-19 T-493 I-5 II-5 II-9

T-453 I-5 II-3 II-20 T-494 I-5 II-5 11-11

T-454 I-5 II-3 11-21 T-495 I-5 II-5 11-12

T-455 I-5 II-3 II-22 T-496 I-5 II-5 11-13

T-456 I-5 II-3 II-23 T-497 I-5 II-5 11-14

T-457 I-5 II-3 II-24 T-498 I-5 II-5 11-15

T-458 I-5 II-3 II-25 T-499 I-5 II-5 11-18

T-459 I-5 II-3 II-26 T-500 I-5 II-5 11-19 Mixture C1 C2 C3 Mixture C1 C2 C3

T-501 I-5 II-5 II-20 T-542 I-5 II-7 II-22

T-502 I-5 II-5 11-21 T-543 I-5 II-7 II-23

T-503 I-5 II-5 II-22 T-544 I-5 II-7 II-24

T-504 I-5 II-5 II-23 T-545 I-5 II-7 II-25

T-505 I-5 II-5 II-24 T-546 I-5 II-7 II-26

T-506 I-5 II-5 II-25 T-547 I-5 II-7 II-27

T-507 I-5 II-5 II-26 T-548 I-5 II-7 II-28

T-508 I-5 II-5 II-27 T-549 I-5 II-7 II-29

T-509 I-5 II-5 II-28 T-550 I-5 II-8 II-9

T-510 I-5 II-5 II-29 T-551 I-5 II-8 11-11

T-511 I-5 II-6 II-7 T-552 I-5 II-8 11-12

T-512 I-5 II-6 II-8 T-553 I-5 II-8 11-13

T-513 I-5 II-6 II-9 T-554 I-5 II-8 11-14

T-514 I-5 II-6 11-11 T-555 I-5 II-8 11-15

T-515 I-5 II-6 11-12 T-556 I-5 II-8 11-18

T-516 I-5 II-6 11-13 T-557 I-5 II-8 11-19

T-517 I-5 II-6 11-14 T-558 I-5 II-8 II-20

T-518 I-5 II-6 11-15 T-559 I-5 II-8 11-21

T-519 I-5 II-6 11-18 T-560 I-5 II-8 II-22

T-520 I-5 II-6 11-19 T-561 I-5 II-8 II-23

T-521 I-5 II-6 II-20 T-562 I-5 II-8 II-24

T-522 I-5 II-6 11-21 T-563 I-5 II-8 II-25

T-523 I-5 II-6 II-22 T-564 I-5 II-8 II-26

T-524 I-5 II-6 II-23 T-565 I-5 II-8 II-27

T-525 I-5 II-6 II-24 T-566 I-5 II-8 II-28

T-526 I-5 II-6 II-25 T-567 I-5 II-8 II-29

T-527 I-5 II-6 II-26 T-568 I-5 II-9 11-11

T-528 I-5 II-6 II-27 T-569 I-5 II-9 11-12

T-529 I-5 II-6 II-28 T-570 I-5 II-9 11-13

T-530 I-5 II-6 II-29 T-571 I-5 II-9 11-14

T-531 I-5 II-7 II-8 T-572 I-5 II-9 11-15

T-532 I-5 II-7 II-9 T-573 I-5 II-9 11-18

T-533 I-5 II-7 11-11 T-574 I-5 II-9 11-19

T-534 I-5 II-7 11-12 T-575 I-5 II-9 II-20

T-535 I-5 II-7 11-13 T-576 I-5 II-9 11-21

T-536 I-5 II-7 11-14 T-577 I-5 II-9 II-22

T-537 I-5 II-7 11-15 T-578 I-5 II-9 II-23

T-538 I-5 II-7 11-18 T-579 I-5 II-9 II-24

T-539 I-5 II-7 11-19 T-580 I-5 II-9 II-25

T-540 I-5 II-7 II-20 T-581 I-5 II-9 II-26

T-541 I-5 II-7 11-21 T-582 I-5 II-9 II-27 Mixture C1 C2 C3 Mixture C1 C2 C3

T-583 I-5 II-9 II-28 T-624 I-5 11-11 II-29

T-584 I-5 II-9 II-29 T-625 I-5 11-12 11-13

T-585 I-5 11-10 11-1 T-626 I-5 11-12 11-14

T-586 I-5 11-10 II-2 T-627 I-5 11-12 11-15

T-587 I-5 11-10 II-3 T-628 I-5 11-12 11-18

T-588 I-5 11-10 II-6 T-629 I-5 11-12 11-19

T-589 I-5 11-10 II-7 T-630 I-5 11-12 II-20

T-590 I-5 11-10 II-8 T-631 I-5 11-12 11-21

T-591 I-5 11-10 II-9 T-632 I-5 11-12 II-22

T-592 I-5 11-10 11-11 T-633 I-5 11-12 II-23

T-593 I-5 11-10 11-12 T-634 I-5 11-12 II-24

T-594 I-5 11-10 11-13 T-635 I-5 11-12 II-25

T-595 I-5 11-10 11-14 T-636 I-5 11-12 II-26

T-596 I-5 11-10 11-15 T-637 I-5 11-12 II-27

T-597 I-5 11-10 11-18 T-638 I-5 11-12 II-28

T-598 I-5 11-10 11-19 T-639 I-5 11-12 II-29

T-599 I-5 11-10 II-20 T-640 I-5 11-13 11-14

T-600 I-5 11-10 11-21 T-641 I-5 11-13 11-15

T-601 I-5 11-10 II-22 T-642 I-5 11-13 11-18

T-602 I-5 11-10 II-23 T-643 I-5 11-13 11-19

T-603 I-5 11-10 II-24 T-644 I-5 11-13 II-20

T-604 I-5 11-10 II-25 T-645 I-5 11-13 11-21

T-605 I-5 11-10 II-26 T-646 I-5 11-13 II-22

T-606 I-5 11-10 II-27 T-647 I-5 11-13 II-23

T-607 I-5 11-10 II-28 T-648 I-5 11-13 II-24

T-608 I-5 11-10 II-29 T-649 I-5 11-13 II-25

T-609 I-5 11-11 11-12 T-650 I-5 11-13 II-26

T-610 I-5 11-11 11-13 T-651 I-5 11-13 II-27

T-611 I-5 11-11 11-14 T-652 I-5 11-13 II-28

T-612 I-5 11-11 11-15 T-653 I-5 11-13 II-29

T-613 I-5 11-11 11-18 T-654 I-5 11-14 11-15

T-614 I-5 11-11 11-19 T-655 I-5 11-14 11-18

T-615 I-5 11-11 II-20 T-656 I-5 11-14 11-19

T-616 I-5 11-11 11-21 T-657 I-5 11-14 II-20

T-617 I-5 11-11 II-22 T-658 I-5 11-14 11-21

T-618 I-5 11-11 II-23 T-659 I-5 11-14 II-22

T-619 I-5 11-11 II-24 T-660 I-5 11-14 II-23

T-620 I-5 11-11 II-25 T-661 I-5 11-14 II-24

T-621 I-5 11-11 II-26 T-662 I-5 11-14 II-25

T-622 I-5 11-11 II-27 T-663 I-5 11-14 II-26

T-623 I-5 11-11 II-28 T-664 I-5 11-14 II-27 Mixture C1 C2 C3 Mixture C1 C2 C3

T-665 I-5 11-14 II-28 T-706 I-5 11-17 II-6

T-666 I-5 11-14 II-29 T-707 I-5 11-17 II-7

T-667 I-5 11-15 11-18 T-708 I-5 11-17 II-8

T-668 I-5 11-15 11-19 T-709 I-5 11-17 II-9

T-669 I-5 11-15 II-20 T-710 I-5 11-17 11-11

T-670 I-5 11-15 11-21 T-711 I-5 11-17 11-12

T-671 I-5 11-15 II-22 T-712 I-5 11-17 11-13

T-672 I-5 11-15 II-23 T-713 I-5 11-17 11-14

T-673 I-5 11-15 II-24 T-714 I-5 11-17 11-15

T-674 I-5 11-15 II-25 T-715 I-5 11-17 11-18

T-675 I-5 11-15 II-26 T-716 I-5 11-17 11-19

T-676 I-5 11-15 II-27 T-717 I-5 11-17 II-20

T-677 I-5 11-15 II-28 T-718 I-5 11-17 11-21

T-678 I-5 11-15 II-29 T-719 I-5 11-17 II-22

T-679 I-5 11-16 11-1 T-720 I-5 11-17 II-23

T-680 I-5 11-16 II-2 T-721 I-5 11-17 II-24

T-681 I-5 11-16 II-3 T-722 I-5 11-17 II-25

T-682 I-5 11-16 II-6 T-723 I-5 11-17 II-26

T-683 I-5 11-16 II-7 T-724 I-5 11-17 II-27

T-684 I-5 11-16 II-8 T-725 I-5 11-17 II-28

T-685 I-5 11-16 II-9 T-726 I-5 11-17 II-29

T-686 I-5 11-16 11-11 T-727 I-5 11-18 11-19

T-687 I-5 11-16 11-12 T-728 I-5 11-18 II-20

T-688 I-5 11-16 11-13 T-729 I-5 11-18 11-21

T-689 I-5 11-16 11-14 T-730 I-5 11-18 II-22

T-690 I-5 11-16 11-15 T-731 I-5 11-18 II-23

T-691 I-5 11-16 11-18 T-732 I-5 11-18 II-24

T-692 I-5 11-16 11-19 T-733 I-5 11-18 II-25

T-693 I-5 11-16 II-20 T-734 I-5 11-18 II-26

T-694 I-5 11-16 11-21 T-735 I-5 11-18 II-27

T-695 I-5 11-16 II-22 T-736 I-5 11-18 II-28

T-696 I-5 11-16 II-23 T-737 I-5 11-18 II-29

T-697 I-5 11-16 II-24 T-738 I-5 11-19 II-20

T-698 I-5 11-16 II-25 T-739 I-5 11-19 11-21

T-699 I-5 11-16 II-26 T-740 I-5 11-19 II-22

T-700 I-5 11-16 II-27 T-741 I-5 11-19 II-23

T-701 I-5 11-16 II-28 T-742 I-5 11-19 II-24

T-702 I-5 11-16 II-29 T-743 I-5 11-19 II-25

T-703 I-5 11-17 11-1 T-744 I-5 11-19 II-26

T-704 I-5 11-17 II-2 T-745 I-5 11-19 II-27

T-705 I-5 11-17 II-3 T-746 I-5 11-19 II-28 Mixture C1 C2 C3 Mixture C1 C2 C3

T-747 I-5 11-19 II-29 T-788 I-5 II-26 II-28

T-748 I-5 II-20 11-21 T-789 I-5 II-26 II-29

T-749 I-5 II-20 II-22 T-790 I-5 II-27 II-28

T-750 I-5 II-20 II-23 T-791 I-5 II-27 II-29

T-751 I-5 II-20 II-24 T-792 I-5 II-28 II-29

T-752 I-5 II-20 II-25 T-793 I-9 11-1 II-2

T-753 I-5 II-20 II-26 T-794 I-9 11-1 II-3

T-754 I-5 II-20 II-27 T-795 I-9 11-1 II-6

T-755 I-5 II-20 II-28 T-796 I-9 11-1 II-7

T-756 I-5 II-20 II-29 T-797 I-9 11-1 II-8

T-757 I-5 11-21 II-22 T-798 I-9 11-1 II-9

T-758 I-5 11-21 II-23 T-799 I-9 11-1 11-11

T-759 I-5 11-21 II-24 T-800 I-9 11-1 11-12

T-760 I-5 11-21 II-25 T-801 I-9 11-1 11-13

T-761 I-5 11-21 II-26 T-802 I-9 11-1 11-14

T-762 I-5 11-21 II-27 T-803 I-9 11-1 11-15

T-763 I-5 11-21 II-28 T-804 I-9 11-1 11-18

T-764 I-5 11-21 II-29 T-805 I-9 11-1 11-19

T-765 I-5 II-22 II-23 T-806 I-9 11-1 II-20

T-766 I-5 II-22 II-24 T-807 I-9 11-1 11-21

T-767 I-5 II-22 II-25 T-808 I-9 11-1 II-22

T-768 I-5 II-22 II-26 T-809 I-9 11-1 II-23

T-769 I-5 II-22 II-27 T-810 I-9 11-1 II-24

T-770 I-5 II-22 II-28 T-811 I-9 11-1 II-25

T-771 I-5 II-22 II-29 T-812 I-9 11-1 II-26

T-772 I-5 II-23 II-24 T-813 I-9 11-1 II-27

T-773 I-5 II-23 II-25 T-814 I-9 11-1 II-28

T-774 I-5 II-23 II-26 T-815 I-9 11-1 II-29

T-775 I-5 II-23 II-27 T-816 I-9 II-2 II-3

T-776 I-5 II-23 II-28 T-817 I-9 II-2 II-6

T-777 I-5 II-23 II-29 T-818 I-9 II-2 II-7

T-778 I-5 II-24 II-25 T-819 I-9 II-2 II-8

T-779 I-5 II-24 II-26 T-820 I-9 II-2 II-9

T-780 I-5 II-24 II-27 T-821 I-9 II-2 11-11

T-781 I-5 II-24 II-28 T-822 I-9 II-2 11-12

T-782 I-5 II-24 II-29 T-823 I-9 II-2 11-13

T-783 I-5 II-25 II-26 T-824 I-9 II-2 11-14

T-784 I-5 II-25 II-27 T-825 I-9 II-2 11-15

T-785 I-5 II-25 II-28 T-826 I-9 II-2 11-18

T-786 I-5 II-25 II-29 T-827 I-9 II-2 11-19

T-787 I-5 II-26 II-27 T-828 I-9 II-2 II-20 Mixture C1 C2 C3 Mixture C1 C2 C3

T-829 I-9 II-2 11-21 T-870 I-9 II-4 11-15

T-830 I-9 II-2 II-22 T-871 I-9 II-4 11-18

T-831 I-9 II-2 II-23 T-872 I-9 II-4 11-19

T-832 I-9 II-2 II-24 T-873 I-9 II-4 II-20

T-833 I-9 II-2 II-25 T-874 I-9 II-4 11-21

T-834 I-9 II-2 II-26 T-875 I-9 II-4 II-22

T-835 I-9 II-2 II-27 T-876 I-9 II-4 II-23

T-836 I-9 II-2 II-28 T-877 I-9 II-4 II-24

T-837 I-9 II-2 II-29 T-878 I-9 II-4 II-25

T-838 I-9 II-3 II-6 T-879 I-9 II-4 II-26

T-839 I-9 II-3 II-7 T-880 I-9 II-4 II-27

T-840 I-9 II-3 II-8 T-881 I-9 II-4 II-28

T-841 I-9 II-3 II-9 T-882 I-9 II-4 II-29

T-842 I-9 II-3 11-11 T-883 I-9 II-5 11-1

T-843 I-9 II-3 11-12 T-884 I-9 II-5 II-2

T-844 I-9 II-3 11-13 T-885 I-9 II-5 II-3

T-845 I-9 II-3 11-14 T-886 I-9 II-5 II-6

T-846 I-9 II-3 11-15 T-887 I-9 II-5 II-7

T-847 I-9 II-3 11-18 T-888 I-9 II-5 II-8

T-848 I-9 II-3 11-19 T-889 I-9 II-5 II-9

T-849 I-9 II-3 II-20 T-890 I-9 II-5 11-11

T-850 I-9 II-3 11-21 T-891 I-9 II-5 11-12

T-851 I-9 II-3 II-22 T-892 I-9 II-5 11-13

T-852 I-9 II-3 II-23 T-893 I-9 II-5 11-14

T-853 I-9 II-3 II-24 T-894 I-9 II-5 11-15

T-854 I-9 II-3 II-25 T-895 I-9 II-5 11-18

T-855 I-9 II-3 II-26 T-896 I-9 II-5 11-19

T-856 I-9 II-3 II-27 T-897 I-9 II-5 II-20

T-857 I-9 II-3 II-28 T-898 I-9 II-5 11-21

T-858 I-9 II-3 II-29 T-899 I-9 II-5 II-22

T-859 I-9 II-4 11-1 T-900 I-9 II-5 II-23

T-860 I-9 II-4 II-2 T-901 I-9 II-5 II-24

T-861 I-9 II-4 II-3 T-902 I-9 II-5 II-25

T-862 I-9 II-4 II-6 T-903 I-9 II-5 II-26

T-863 I-9 II-4 II-7 T-904 I-9 II-5 II-27

T-864 I-9 II-4 II-8 T-905 I-9 II-5 II-28

T-865 I-9 II-4 II-9 T-906 I-9 II-5 II-29

T-866 I-9 II-4 11-11 T-907 I-9 II-6 II-7

T-867 I-9 II-4 11-12 T-908 I-9 II-6 II-8

T-868 I-9 II-4 11-13 T-909 I-9 II-6 II-9

T-869 I-9 II-4 11-14 T-910 I-9 II-6 11-11 Mixture C1 C2 C3 Mixture C1 C2 C3

T-911 I-9 II-6 11-12 T-952 I-9 II-8 11-18

T-912 I-9 II-6 11-13 T-953 I-9 II-8 11-19

T-913 I-9 II-6 11-14 T-954 I-9 II-8 II-20

T-914 I-9 II-6 11-15 T-955 I-9 II-8 11-21

T-915 I-9 II-6 11-18 T-956 I-9 II-8 II-22

T-916 I-9 II-6 11-19 T-957 I-9 II-8 II-23

T-917 I-9 II-6 II-20 T-958 I-9 II-8 II-24

T-918 I-9 II-6 11-21 T-959 I-9 II-8 II-25

T-919 I-9 II-6 II-22 T-960 I-9 II-8 II-26

T-920 I-9 II-6 II-23 T-961 I-9 II-8 II-27

T-921 I-9 II-6 II-24 T-962 I-9 II-8 II-28

T-922 I-9 II-6 II-25 T-963 I-9 II-8 II-29

T-923 I-9 II-6 II-26 T-964 I-9 II-9 11-11

T-924 I-9 II-6 II-27 T-965 I-9 II-9 11-12

T-925 I-9 II-6 II-28 T-966 I-9 II-9 11-13

T-926 I-9 II-6 II-29 T-967 I-9 II-9 11-14

T-927 I-9 II-7 II-8 T-968 I-9 II-9 11-15

T-928 I-9 II-7 II-9 T-969 I-9 II-9 11-18

T-929 I-9 II-7 11-11 T-970 I-9 II-9 11-19

T-930 I-9 II-7 11-12 T-971 I-9 II-9 II-20

T-931 I-9 II-7 11-13 T-972 I-9 II-9 11-21

T-932 I-9 II-7 11-14 T-973 I-9 II-9 II-22

T-933 I-9 II-7 11-15 T-974 I-9 II-9 II-23

T-934 I-9 II-7 11-18 T-975 I-9 II-9 II-24

T-935 I-9 II-7 11-19 T-976 I-9 II-9 II-25

T-936 I-9 II-7 II-20 T-977 I-9 II-9 II-26

T-937 I-9 II-7 11-21 T-978 I-9 II-9 II-27

T-938 I-9 II-7 II-22 T-979 I-9 II-9 II-28

T-939 I-9 II-7 II-23 T-980 I-9 II-9 II-29

T-940 I-9 II-7 II-24 T-981 I-9 11-10 11-1

T-941 I-9 II-7 II-25 T-982 I-9 11-10 II-2

T-942 I-9 II-7 II-26 T-983 I-9 11-10 II-3

T-943 I-9 II-7 II-27 T-984 I-9 11-10 II-6

T-944 I-9 II-7 II-28 T-985 I-9 11-10 II-7

T-945 I-9 II-7 II-29 T-986 I-9 11-10 II-8

T-946 I-9 II-8 II-9 T-987 I-9 11-10 II-9

T-947 I-9 II-8 11-11 T-988 I-9 11-10 11-11

T-948 I-9 II-8 11-12 T-989 I-9 11-10 11-12

T-949 I-9 II-8 11-13 T-990 I-9 11-10 11-13

T-950 I-9 II-8 11-14 T-991 I-9 11-10 11-14

T-951 I-9 II-8 11-15 T-992 I-9 11-10 11-15 Mixture C1 C2 C3 Mixture C1 C2 C3

T-993 I-9 11-10 11-18 T-1034 I-9 11-12 II-28

T-994 I-9 11-10 11-19 T-1035 I-9 11-12 II-29

T-995 I-9 11-10 II-20 T-1036 I-9 11-13 11-14

T-996 I-9 11-10 11-21 T-1037 I-9 11-13 11-15

T-997 I-9 11-10 II-22 T-1038 I-9 11-13 11-18

T-998 I-9 11-10 II-23 T-1039 I-9 11-13 11-19

T-999 I-9 11-10 II-24 T-1040 I-9 11-13 II-20

T-1000 I-9 11-10 II-25 T-1041 I-9 11-13 11-21

T-1001 I-9 11-10 II-26 T-1042 I-9 11-13 II-22

T-1002 I-9 11-10 II-27 T-1043 I-9 11-13 II-23

T-1003 I-9 11-10 II-28 T-1044 I-9 11-13 II-24

T-1004 I-9 11-10 II-29 T-1045 I-9 11-13 II-25

T-1005 I-9 11-11 11-12 T-1046 I-9 11-13 II-26

T-1006 I-9 11-11 11-13 T-1047 I-9 11-13 II-27

T-1007 I-9 11-11 11-14 T-1048 I-9 11-13 II-28

T-1008 I-9 11-11 11-15 T-1049 I-9 11-13 II-29

T-1009 I-9 11-11 11-18 T-1050 I-9 11-14 11-15

T-1010 I-9 11-11 11-19 T-1051 I-9 11-14 11-18

T-1011 I-9 11-11 II-20 T-1052 I-9 11-14 11-19

T-1012 I-9 11-11 11-21 T-1053 I-9 11-14 II-20

T-1013 I-9 11-11 II-22 T-1054 I-9 11-14 11-21

T-1014 I-9 11-11 II-23 T-1055 I-9 11-14 II-22

T-1015 I-9 11-11 II-24 T-1056 I-9 11-14 II-23

T-1016 I-9 11-11 II-25 T-1057 I-9 11-14 II-24

T-1017 I-9 11-11 II-26 T-1058 I-9 11-14 II-25

T-1018 I-9 11-11 II-27 T-1059 I-9 11-14 II-26

T-1019 I-9 11-11 II-28 T-1060 I-9 11-14 II-27

T-1020 I-9 11-11 II-29 T-1061 I-9 11-14 II-28

T-1021 I-9 11-12 11-13 T-1062 I-9 11-14 II-29

T-1022 I-9 11-12 11-14 T-1063 I-9 11-15 11-18

T-1023 I-9 11-12 11-15 T-1064 I-9 11-15 11-19

T-1024 I-9 11-12 11-18 T-1065 I-9 11-15 II-20

T-1025 I-9 11-12 11-19 T-1066 I-9 11-15 11-21

T-1026 I-9 11-12 II-20 T-1067 I-9 11-15 II-22

T-1027 I-9 11-12 11-21 T-1068 I-9 11-15 II-23

T-1028 I-9 11-12 II-22 T-1069 I-9 11-15 II-24

T-1029 I-9 11-12 II-23 T-1070 I-9 11-15 II-25

T-1030 I-9 11-12 II-24 T-1071 I-9 11-15 II-26

T-1031 I-9 11-12 II-25 T-1072 I-9 11-15 II-27

T-1032 I-9 11-12 II-26 T-1073 I-9 11-15 II-28

T-1033 I-9 11-12 II-27 T-1074 I-9 11-15 II-29 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1075 I-9 11-16 11-1 T-1116 I-9 11-17 II-23

T-1076 I-9 11-16 II-2 T-1117 I-9 11-17 II-24

T-1077 I-9 11-16 II-3 T-1118 I-9 11-17 II-25

T-1078 I-9 11-16 II-6 T-1119 I-9 11-17 II-26

T-1079 I-9 11-16 II-7 T-1120 I-9 11-17 II-27

T-1080 I-9 11-16 II-8 T-1121 I-9 11-17 II-28

T-1081 I-9 11-16 II-9 T-1122 I-9 11-17 II-29

T-1082 I-9 11-16 11-11 T-1123 I-9 11-18 11-19

T-1083 I-9 11-16 11-12 T-1124 I-9 11-18 II-20

T-1084 I-9 11-16 11-13 T-1125 I-9 11-18 11-21

T-1085 I-9 11-16 11-14 T-1126 I-9 11-18 II-22

T-1086 I-9 11-16 11-15 T-1127 I-9 11-18 II-23

T-1087 I-9 11-16 11-18 T-1128 I-9 11-18 II-24

T-1088 I-9 11-16 11-19 T-1129 I-9 11-18 II-25

T-1089 I-9 11-16 II-20 T-1130 I-9 11-18 II-26

T-1090 I-9 11-16 11-21 T-1131 I-9 11-18 II-27

T-1091 I-9 11-16 II-22 T-1132 I-9 11-18 II-28

T-1092 I-9 11-16 II-23 T-1133 I-9 11-18 II-29

T-1093 I-9 11-16 II-24 T-1134 I-9 11-19 II-20

T-1094 I-9 11-16 II-25 T-1135 I-9 11-19 11-21

T-1095 I-9 11-16 II-26 T-1136 I-9 11-19 II-22

T-1096 I-9 11-16 II-27 T-1137 I-9 11-19 II-23

T-1097 I-9 11-16 II-28 T-1138 I-9 11-19 II-24

T-1098 I-9 11-16 II-29 T-1139 I-9 11-19 II-25

T-1099 I-9 11-17 11-1 T-1140 I-9 11-19 II-26

T-1100 I-9 11-17 II-2 T-1141 I-9 11-19 II-27

T-1101 I-9 11-17 II-3 T-1142 I-9 11-19 II-28

T-1102 I-9 11-17 II-6 T-1143 I-9 11-19 II-29

T-1103 I-9 11-17 II-7 T-1144 I-9 II-20 11-21

T-1104 I-9 11-17 II-8 T-1145 I-9 II-20 II-22

T-1105 I-9 11-17 II-9 T-1146 I-9 II-20 II-23

T-1106 I-9 11-17 11-11 T-1147 I-9 II-20 II-24

T-1107 I-9 11-17 11-12 T-1148 I-9 II-20 II-25

T-1108 I-9 11-17 11-13 T-1149 I-9 II-20 II-26

T-1109 I-9 11-17 11-14 T-1150 I-9 II-20 II-27

T-1110 I-9 11-17 11-15 T-1151 I-9 II-20 II-28

T-1111 I-9 11-17 11-18 T-1152 I-9 II-20 II-29

T-1112 I-9 11-17 11-19 T-1153 I-9 11-21 II-22

T-1113 I-9 11-17 II-20 T-1154 I-9 11-21 II-23

T-1114 I-9 11-17 11-21 T-1155 I-9 11-21 II-24

T-1115 I-9 11-17 II-22 T-1156 I-9 11-21 II-25 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1157 I-9 11-21 II-26 T-1198 1-11 11-1 11-14

T-1158 I-9 11-21 II-27 T-1199 1-11 11-1 11-15

T-1159 I-9 11-21 II-28 T-1200 1-11 11-1 11-18

T-1160 I-9 11-21 II-29 T-1201 1-11 11-1 11-19

T-1161 I-9 II-22 II-23 T-1202 1-11 11-1 II-20

T-1162 I-9 II-22 II-24 T-1203 1-11 11-1 11-21

T-1163 I-9 II-22 II-25 T-1204 1-11 11-1 II-22

T-1164 I-9 II-22 II-26 T-1205 1-11 11-1 II-23

T-1165 I-9 II-22 II-27 T-1206 1-11 11-1 II-24

T-1166 I-9 II-22 II-28 T-1207 1-11 11-1 II-25

T-1167 I-9 II-22 II-29 T-1208 1-11 11-1 II-26

T-1168 I-9 II-23 II-24 T-1209 1-11 11-1 II-27

T-1169 I-9 II-23 II-25 T-1210 1-11 11-1 II-28

T-1170 I-9 II-23 II-26 T-1211 1-11 11-1 II-29

T-1171 I-9 II-23 II-27 T-1212 1-11 II-2 II-3

T-1172 I-9 II-23 II-28 T-1213 1-11 II-2 II-6

T-1173 I-9 II-23 II-29 T-1214 1-11 II-2 II-7

T-1174 I-9 II-24 II-25 T-1215 1-11 II-2 II-8

T-1175 I-9 II-24 II-26 T-1216 1-11 II-2 11-11

T-1176 I-9 II-24 II-27 T-1217 1-11 II-2 11-11

T-1177 I-9 II-24 II-28 T-1218 1-11 II-2 11-12

T-1178 I-9 II-24 II-29 T-1219 1-11 II-2 11-13

T-1179 I-9 II-25 II-26 T-1220 1-11 II-2 11-14

T-1180 I-9 II-25 II-27 T-1221 1-11 II-2 11-15

T-1181 I-9 II-25 II-28 T-1222 1-11 II-2 11-18

T-1182 I-9 II-25 II-29 T-1223 1-11 II-2 11-19

T-1183 I-9 II-26 II-27 T-1224 1-11 II-2 II-20

T-1184 I-9 II-26 II-28 T-1225 1-11 II-2 11-21

T-1185 I-9 II-26 II-29 T-1226 1-11 II-2 II-22

T-1186 I-9 II-27 II-28 T-1227 1-11 II-2 II-23

T-1187 I-9 II-27 II-29 T-1228 1-11 II-2 II-24

T-1188 I-9 II-28 II-29 T-1229 1-11 II-2 II-25

T-1189 1-11 11-1 II-2 T-1230 1-11 II-2 II-26

T-1190 1-11 11-1 II-3 T-1231 1-11 II-2 II-27

T-1191 1-11 11-1 II-6 T-1232 1-11 II-2 II-28

T-1192 1-11 11-1 II-7 T-1233 1-11 II-2 II-29

T-1193 1-11 11-1 II-8 T-1234 1-11 II-3 II-6

T-1194 1-11 11-1 11-11 T-1235 1-11 II-3 II-7

T-1195 1-11 11-1 11-11 T-1236 1-11 II-3 II-8

T-1196 1-11 11-1 11-12 T-1237 1-11 II-3 11-11

T-1197 1-11 11-1 11-13 T-1238 1-11 II-3 11-11 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1239 1-11 II-3 11-12 T-1280 1-11 II-5 II-2

T-1240 1-11 II-3 11-13 T-1281 1-11 II-5 II-3

T-1241 1-11 II-3 11-14 T-1282 1-11 II-5 II-6

T-1242 1-11 II-3 11-15 T-1283 1-11 II-5 II-7

T-1243 1-11 II-3 11-18 T-1284 1-11 II-5 II-8

T-1244 1-11 II-3 11-19 T-1285 1-11 II-5 11-11

T-1245 1-11 II-3 II-20 T-1286 1-11 II-5 11-11

T-1246 1-11 II-3 11-21 T-1287 1-11 II-5 11-12

T-1247 1-11 II-3 II-22 T-1288 1-11 II-5 11-13

T-1248 1-11 II-3 II-23 T-1289 1-11 II-5 11-14

T-1249 1-11 II-3 II-24 T-1290 1-11 II-5 11-15

T-1250 1-11 II-3 II-25 T-1291 1-11 II-5 11-18

T-1251 1-11 II-3 II-26 T-1292 1-11 II-5 11-19

T-1252 1-11 II-3 II-27 T-1293 1-11 II-5 II-20

T-1253 1-11 II-3 II-28 T-1294 1-11 II-5 11-21

T-1254 1-11 II-3 II-29 T-1295 1-11 II-5 II-22

T-1255 1-11 II-4 11-1 T-1296 1-11 II-5 II-23

T-1256 1-11 II-4 II-2 T-1297 1-11 II-5 II-24

T-1257 1-11 II-4 II-3 T-1298 1-11 II-5 II-25

T-1258 1-11 II-4 II-6 T-1299 1-11 II-5 II-26

T-1259 1-11 II-4 II-7 T-1300 1-11 II-5 II-27

T-1260 1-11 II-4 II-8 T-1301 1-11 II-5 II-28

T-1261 1-11 II-4 11-11 T-1302 1-11 II-5 II-29

T-1262 1-11 II-4 11-11 T-1303 1-11 II-6 II-7

T-1263 1-11 II-4 11-12 T-1304 1-11 II-6 II-8

T-1264 1-11 II-4 11-13 T-1305 1-11 II-6 11-11

T-1265 1-11 II-4 11-14 T-1306 1-11 II-6 11-11

T-1266 1-11 II-4 11-15 T-1307 1-11 II-6 11-12

T-1267 1-11 II-4 11-18 T-1308 1-11 II-6 11-13

T-1268 1-11 II-4 11-19 T-1309 1-11 II-6 11-14

T-1269 1-11 II-4 II-20 T-1310 1-11 II-6 11-15

T-1270 1-11 II-4 11-21 T-1311 1-11 II-6 11-18

T-1271 1-11 II-4 II-22 T-1312 1-11 II-6 11-19

T-1272 1-11 II-4 II-23 T-1313 1-11 II-6 II-20

T-1273 1-11 II-4 II-24 T-1314 1-11 II-6 11-21

T-1274 1-11 II-4 II-25 T-1315 1-11 II-6 II-22

T-1275 1-11 II-4 II-26 T-1316 1-11 II-6 II-23

T-1276 1-11 II-4 II-27 T-1317 1-11 II-6 II-24

T-1277 1-11 II-4 II-28 T-1318 1-11 II-6 II-25

T-1278 1-11 II-4 II-29 T-1319 1-11 II-6 II-26

T-1279 1-11 II-5 11-1 T-1320 1-11 II-6 II-27 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1321 1-11 II-6 II-28 T-1362 1-11 11-11 11-13

T-1322 1-11 II-6 II-29 T-1363 1-11 11-11 11-14

T-1323 1-11 II-7 II-8 T-1364 1-11 11-11 11-15

T-1324 1-11 II-7 11-11 T-1365 1-11 11-11 11-18

T-1325 1-11 II-7 11-11 T-1366 1-11 11-11 11-19

T-1326 1-11 II-7 11-12 T-1367 1-11 11-11 II-20

T-1327 1-11 II-7 11-13 T-1368 1-11 11-11 11-21

T-1328 1-11 II-7 11-14 T-1369 1-11 11-11 II-22

T-1329 1-11 II-7 11-15 T-1370 1-11 11-11 II-23

T-1330 1-11 II-7 11-18 T-1371 1-11 11-11 II-24

T-1331 1-11 II-7 11-19 T-1372 1-11 11-11 II-25

T-1332 1-11 II-7 II-20 T-1373 1-11 11-11 II-26

T-1333 1-11 II-7 11-21 T-1374 1-11 11-11 II-27

T-1334 1-11 II-7 II-22 T-1375 1-11 11-11 II-28

T-1335 1-11 II-7 II-23 T-1376 1-11 11-11 II-29

T-1336 1-11 II-7 II-24 T-1377 1-11 11-11 11-1

T-1337 1-11 II-7 II-25 T-1378 1-11 11-11 II-2

T-1338 1-11 II-7 II-26 T-1379 1-11 11-11 II-3

T-1339 1-11 II-7 II-27 T-1380 1-11 11-11 II-6

T-1340 1-11 II-7 II-28 T-1381 1-11 11-11 II-7

T-1341 1-11 II-7 II-29 T-1382 1-11 11-11 II-8

T-1342 1-11 II-8 11-11 T-1383 1-11 11-11 11-11

T-1343 1-11 II-8 11-11 T-1384 1-11 11-11 11-11

T-1344 1-11 II-8 11-12 T-1385 1-11 11-11 11-12

T-1345 1-11 II-8 11-13 T-1386 1-11 11-11 11-13

T-1346 1-11 II-8 11-14 T-1387 1-11 11-11 11-14

T-1347 1-11 II-8 11-15 T-1388 1-11 11-11 11-15

T-1348 1-11 II-8 11-18 T-1389 1-11 11-11 11-18

T-1349 1-11 II-8 11-19 T-1390 1-11 11-11 11-19

T-1350 1-11 II-8 II-20 T-1391 1-11 11-11 II-20

T-1351 1-11 II-8 11-21 T-1392 1-11 11-11 11-21

T-1352 1-11 II-8 II-22 T-1393 1-11 11-11 II-22

T-1353 1-11 II-8 II-23 T-1394 1-11 11-11 II-23

T-1354 1-11 II-8 II-24 T-1395 1-11 11-11 II-24

T-1355 1-11 II-8 II-25 T-1396 1-11 11-11 II-25

T-1356 1-11 II-8 II-26 T-1397 1-11 11-11 II-26

T-1357 1-11 II-8 II-27 T-1398 1-11 11-11 II-27

T-1358 1-11 II-8 II-28 T-1399 1-11 11-11 II-28

T-1359 1-11 II-8 II-29 T-1400 1-11 11-11 II-29

T-1360 1-11 11-11 11-11 T-1401 1-11 11-11 11-12

T-1361 1-11 11-11 11-12 T-1402 1-11 11-11 11-13 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1403 1-11 11-11 11-14 T-1444 1-11 11-13 II-28

T-1404 1-11 11-11 11-15 T-1445 1-11 11-13 II-29

T-1405 1-11 11-11 11-18 T-1446 1-11 11-14 11-15

T-1406 1-11 11-11 11-19 T-1447 1-11 11-14 11-18

T-1407 1-11 11-11 II-20 T-1448 1-11 11-14 11-19

T-1408 1-11 11-11 11-21 T-1449 1-11 11-14 II-20

T-1409 1-11 11-11 II-22 T-1450 1-11 11-14 11-21

T-1410 1-11 11-11 II-23 T-1451 1-11 11-14 II-22

T-1411 1-11 11-11 II-24 T-1452 1-11 11-14 II-23

T-1412 1-11 11-11 II-25 T-1453 1-11 11-14 II-24

T-1413 1-11 11-11 II-26 T-1454 1-11 11-14 II-25

T-1414 1-11 11-11 II-27 T-1455 1-11 11-14 II-26

T-1415 1-11 11-11 II-28 T-1456 1-11 11-14 II-27

T-1416 1-11 11-11 II-29 T-1457 1-11 11-14 II-28

T-1417 1-11 11-12 11-13 T-1458 1-11 11-14 II-29

T-1418 1-11 11-12 11-14 T-1459 1-11 11-15 11-18

T-1419 1-11 11-12 11-15 T-1460 1-11 11-15 11-19

T-1420 1-11 11-12 11-18 T-1461 1-11 11-15 II-20

T-1421 1-11 11-12 11-19 T-1462 1-11 11-15 11-21

T-1422 1-11 11-12 II-20 T-1463 1-11 11-15 II-22

T-1423 1-11 11-12 11-21 T-1464 1-11 11-15 II-23

T-1424 1-11 11-12 II-22 T-1465 1-11 11-15 II-24

T-1425 1-11 11-12 II-23 T-1466 1-11 11-15 II-25

T-1426 1-11 11-12 II-24 T-1467 1-11 11-15 II-26

T-1427 1-11 11-12 II-25 T-1468 1-11 11-15 II-27

T-1428 1-11 11-12 II-26 T-1469 1-11 11-15 II-28

T-1429 1-11 11-12 II-27 T-1470 1-11 11-15 II-29

T-1430 1-11 11-12 II-28 T-1471 1-11 11-16 11-1

T-1431 1-11 11-12 II-29 T-1472 1-11 11-16 II-2

T-1432 1-11 11-13 11-14 T-1473 1-11 11-16 II-3

T-1433 1-11 11-13 11-15 T-1474 1-11 11-16 II-6

T-1434 1-11 11-13 11-18 T-1475 1-11 11-16 II-7

T-1435 1-11 11-13 11-19 T-1476 1-11 11-16 II-8

T-1436 1-11 11-13 II-20 T-1477 1-11 11-16 11-11

T-1437 1-11 11-13 11-21 T-1478 1-11 11-16 11-11

T-1438 1-11 11-13 II-22 T-1479 1-11 11-16 11-12

T-1439 1-11 11-13 II-23 T-1480 1-11 11-16 11-13

T-1440 1-11 11-13 II-24 T-1481 1-11 11-16 11-14

T-1441 1-11 11-13 II-25 T-1482 1-11 11-16 11-15

T-1442 1-11 11-13 II-26 T-1483 1-11 11-16 11-18

T-1443 1-11 11-13 II-27 T-1484 1-11 11-16 11-19 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1485 1-11 11-16 II-20 T-1526 1-11 11-18 II-26

T-1486 1-11 11-16 11-21 T-1527 1-11 11-18 II-27

T-1487 1-11 11-16 II-22 T-1528 1-11 11-18 II-28

T-1488 1-11 11-16 II-23 T-1529 1-11 11-18 II-29

T-1489 1-11 11-16 II-24 T-1530 1-11 11-19 II-20

T-1490 1-11 11-16 II-25 T-1531 1-11 11-19 11-21

T-1491 1-11 11-16 II-26 T-1532 1-11 11-19 II-22

T-1492 1-11 11-16 II-27 T-1533 1-11 11-19 II-23

T-1493 1-11 11-16 II-28 T-1534 1-11 11-19 II-24

T-1494 1-11 11-16 II-29 T-1535 1-11 11-19 II-25

T-1495 1-11 11-17 11-1 T-1536 1-11 11-19 II-26

T-1496 1-11 11-17 II-2 T-1537 1-11 11-19 II-27

T-1497 1-11 11-17 II-3 T-1538 1-11 11-19 II-28

T-1498 1-11 11-17 II-6 T-1539 1-11 11-19 II-29

T-1499 1-11 11-17 II-7 T-1540 1-11 II-20 11-21

T-1500 1-11 11-17 II-8 T-1541 1-11 II-20 II-22

T-1501 1-11 11-17 11-11 T-1542 1-11 II-20 II-23

T-1502 1-11 11-17 11-11 T-1543 1-11 II-20 II-24

T-1503 1-11 11-17 11-12 T-1544 1-11 II-20 II-25

T-1504 1-11 11-17 11-13 T-1545 1-11 II-20 II-26

T-1505 1-11 11-17 11-14 T-1546 1-11 II-20 II-27

T-1506 1-11 11-17 11-15 T-1547 1-11 II-20 II-28

T-1507 1-11 11-17 11-18 T-1548 1-11 II-20 II-29

T-1508 1-11 11-17 11-19 T-1549 1-11 11-21 II-22

T-1509 1-11 11-17 II-20 T-1550 1-11 11-21 II-23

T-1510 1-11 11-17 11-21 T-1551 1-11 11-21 II-24

T-1511 1-11 11-17 II-22 T-1552 1-11 11-21 II-25

T-1512 1-11 11-17 II-23 T-1553 1-11 11-21 II-26

T-1513 1-11 11-17 II-24 T-1554 1-11 11-21 II-27

T-1514 1-11 11-17 II-25 T-1555 1-11 11-21 II-28

T-1515 1-11 11-17 II-26 T-1556 1-11 11-21 II-29

T-1516 1-11 11-17 II-27 T-1557 1-11 II-22 II-23

T-1517 1-11 11-17 II-28 T-1558 1-11 II-22 II-24

T-1518 1-11 11-17 II-29 T-1559 1-11 II-22 II-25

T-1519 1-11 11-18 11-19 T-1560 1-11 II-22 II-26

T-1520 1-11 11-18 II-20 T-1561 1-11 II-22 II-27

T-1521 1-11 11-18 11-21 T-1562 1-11 II-22 II-28

T-1522 1-11 11-18 II-22 T-1563 1-11 II-22 II-29

T-1523 1-11 11-18 II-23 T-1564 1-11 II-23 II-24

T-1524 1-11 11-18 II-24 T-1565 1-11 II-23 II-25

T-1525 1-11 11-18 II-25 T-1566 1-11 II-23 II-26 Mixture C1 C2 C3 Mixture C1 C2 C3

T-1567 1-1 1 II-23 II-27 T-1577 1-1 1 II-25 II-28

T-1568 1-1 1 II-23 II-28 T-1578 1-1 1 II-25 II-29

T-1569 1-1 1 II-23 II-29 T-1579 1-1 1 II-26 II-27

T-1570 1-1 1 II-24 II-25 T-1580 1-1 1 II-26 II-28

T-1571 1-1 1 II-24 II-26 T-1581 1-1 1 II-26 II-29

T-1572 1-1 1 II-24 II-27 T-1582 1-1 1 II-27 II-28

T-1573 1-1 1 II-24 II-28 T-1583 1-1 1 II-27 II-29

T-1574 1-1 1 II-24 II-29 T-1584 1-1 1 II-28 II-29

T-1575 1-1 1 II-25 II-26

T-1576 1-1 1 II-25 II-27

The following components are further preferred components of mixtures comprising three components:

Preferred component 2:

II -1 epoxiconazole

II -2 metconazole

II -6 triticonazole

II -7 prothioconazole

II -9 pyraclostrobin

II -15 fenpropimorph

II -21 chlorothalonil

II -22 metrafenone

II -23 bixafen

II -24 boscalid

II -25 fluxapyroxad

II -27 isopyrazam

II -28 fluopyram

Preferred component 3:

II-30 cyflufenamid

II-33 proquinazid

II-37 prochloraz

II-39 difenoconazole

Accordingly, particularly preferred mixtures are the mixtures of Table T1 , where each row corresponds to one aspect of the mixtures according to the invention. According to one specific aspect, these are ternary mixtures which each only contain these three components as the active compound.

Table T1 : Mixtures comprising one component 1 selected from preferred compounds of the formula I, one component 2 selected from the preferred compounds for component 2 and one component 3 selected from the compounds preferred for component 3. In the table below, each row of a mixture according to the invention corresponds to each mixture component 1 to 3 given in the corresponding row. "C" denotes "component".

Figure imgf000071_0001
Figure imgf000072_0001
Table T1 Components

Mixture C 1 C2 C3

T1-180 1-11 11-15 II-39

T1-181 1-11 11-21 II-30

T1-182 1-11 11-21 II-33

T1-183 1-11 11-21 II-37

T1-184 1-11 11-21 II-39

T1-185 1-11 II-22 II-30

T1-186 1-11 II-22 II-33

T1-187 1-11 II-22 II-37

T1-188 1-11 II-22 II-39

T1-189 1-11 II-23 II-30

T1-190 1-11 II-23 II-33

T1-191 1-11 II-23 II-37

T1-192 1-11 II-23 II-39

T1-193 1-11 II-24 II-30

T1-194 1-11 II-24 II-33

T1-195 1-11 II-24 II-37

T1-196 1-11 II-24 II-39

T1-197 1-11 II-25 II-30

T1-198 1-11 II-25 II-33

T1-199 1-11 II-25 II-37

T1-200 1-11 II-25 II-39

T1-201 1-11 II-27 II-30

T1-202 1-11 II-27 II-33

T1-203 1-11 II-27 II-37

T1-204 1-11 II-27 II-39

T1-205 1-11 II-28 II-30

T1-206 1-11 II-28 II-33

T1-207 1-11 II-28 II-37

T1-208 1-11 II-28 II-39

Figure imgf000073_0001

According to a further embodiment, preference is given to mixtures comprising a component 1, a component 2 and a component 3, where preference is given in particular to those mixtures in which component 2 is a compound II selected from the group of the compounds

11-1 epoxiconazole II-7 prothioconazole

II-2 metconazole 10 II-9 pyraclostrobin

II-6 triticonazole 11-15 fenpropimorph 11-21 chlorothalonil 28 fluopyram

II-22 metrafenone 30 cyflufenamid

II-23 bixafen 33 proquinazid

II-24 boscalid 10 37 prochloraz

II-25 fluxapyroxad 39 difenoconazole

II-27 isopyrazam

and component 3 is a compound II selected from the compounds

II-45 mepiquat chloride

II-46 chlormequat chloride

II-47 trinexapac-ethyl

II-48 prohexadione-calcium

Such mixtures according to the invention are listed explicitly in Table T2. According to specific embodiment, these are ternary mixtures comprising, as active compounds, in each case only these three components.

Table T2: Mixtures comprising, as component 1 , the compound I, a component 2 selected from the active compounds preferred for component 2 and a component 3 selected from the active compounds preferred for component 3. In the table below, in each case one row of a mixture according to the invention corresponds to the respective mixture components 1 to 3 listed in the row in question. "C" denotes "component", "M" denotes "mixture".

M C1 C2 C3 M C1 C2 C3

T2-1 1-1 11-1 II-45 T2-17 1-1 II-9 II-45

T2-2 1-1 11-1 II-46 T2-18 1-1 II-9 II-46

T2-3 1-1 11-1 II-47 T2-19 1-1 II-9 II-47

T2-4 1-1 11-1 II-48 T2-20 1-1 II-9 II-48

T2-5 1-1 II-2 II-45 T2-21 1-1 11-15 II-45

T2-6 1-1 II-2 II-46 T2-22 1-1 11-15 II-46

T2-7 1-1 II-2 II-47 T2-23 1-1 11-15 II-47

T2-8 1-1 II-2 II-48 T2-24 1-1 11-15 II-48

T2-9 1-1 II-6 II-45 T2-25 1-1 11-21 II-45

T2-10 1-1 II-6 II-46 T2-26 1-1 11-21 II-46

T2-1 1 1-1 II-6 II-47 T2-27 1-1 11-21 II-47

T2-12 1-1 II-6 II-48 T2-28 1-1 11-21 II-48

T2-13 1-1 II-7 II-45 T2-29 1-1 II-22 II-45

T2-14 1-1 II-7 II-46 T2-30 1-1 II-22 II-46

T2-15 1-1 II-7 II-47 T2-31 1-1 II-22 II-47

T2-16 1-1 II-7 II-48 T2-32 1-1 II-22 II-48 M C1 C2 C3 M C1 C2 C3

T2-33 1-1 II-23 II-45 T2-71 I-5 11-1 II-47

T2-34 1-1 II-23 II-46 T2-72 I-5 11-1 II-48

T2-35 1-1 II-23 II-47 T2-73 I-5 II-2 II-45

T2-36 1-1 II-23 II-48 T2-74 I-5 II-2 II-46

T2-37 1-1 II-24 II-45 T2-75 I-5 II-2 II-47

T2-38 1-1 II-24 II-46 T2-76 I-5 II-2 II-48

T2-39 1-1 II-24 II-47 T2-77 I-5 II-6 II-45

T2-40 1-1 II-24 II-48 T2-78 I-5 II-6 II-46

T2-41 1-1 II-25 II-45 T2-79 I-5 II-6 II-47

T2-42 1-1 II-25 II-46 T2-80 I-5 II-6 II-48

T2-43 1-1 II-25 II-47 T2-81 I-5 II-7 II-45

T2-44 1-1 II-25 II-48 T2-82 I-5 II-7 II-46

T2-45 1-1 II-27 II-45 T2-83 I-5 II-7 II-47

T2-46 1-1 II-27 II-46 T2-84 I-5 II-7 II-48

T2-47 1-1 II-27 II-47 T2-85 I-5 II-9 II-45

T2-48 1-1 II-27 II-48 T2-86 I-5 II-9 II-46

T2-49 1-1 II-28 II-45 T2-87 I-5 II-9 II-47

T2-50 1-1 II-28 II-46 T2-88 I-5 II-9 II-48

T2-51 1-1 II-28 II-47 T2-89 I-5 11-15 II-45

T2-52 1-1 II-28 II-48 T2-90 I-5 11-15 II-46

T2-53 1-1 II-30 II-45 T2-91 I-5 11-15 II-47

T2-54 1-1 II-30 II-46 T2-92 I-5 11-15 II-48

T2-55 1-1 II-30 II-47 T2-93 I-5 11-21 II-45

T2-56 1-1 II-30 II-48 T2-94 I-5 11-21 II-46

T2-57 1-1 II-33 II-45 T2-95 I-5 11-21 II-47

T2-58 1-1 II-33 II-46 T2-96 I-5 11-21 II-48

T2-59 1-1 II-33 II-47 T2-97 I-5 II-22 II-45

T2-60 1-1 II-33 II-48 T2-98 I-5 II-22 II-46

T2-61 1-1 II-37 II-45 T2-99 I-5 II-22 II-47

T2-62 1-1 II-37 II-46 T2-100 I-5 II-22 II-48

T2-63 1-1 II-37 II-47 T2-101 I-5 II-23 II-45

T2-64 1-1 II-37 II-48 T2-102 I-5 II-23 II-46

T2-65 1-1 II-39 II-45 T2-103 I-5 II-23 II-47

T2-66 1-1 II-39 II-46 T2-104 I-5 II-23 II-48

T2-67 1-1 II-39 II-47 T2-105 I-5 II-24 II-45

T2-68 1-1 II-39 II-48 T2-106 I-5 II-24 II-46

T2-69 I-5 11-1 II-45 T2-107 I-5 II-24 II-47

T2-70 I-5 11-1 II-46 T2-108 I-5 II-24 II-48 M C1 C2 C3 M C1 C2 C3

T2-109 I-5 II-25 II-45 T2-147 I-9 II-6 II-47

T2-110 I-5 II-25 II-46 T2-148 I-9 II-6 II-48

T2-111 I-5 II-25 II-47 T2-149 I-9 II-7 II-45

T2-112 I-5 II-25 II-48 T2-150 I-9 II-7 II-46

T2-113 I-5 II-27 II-45 T2-151 I-9 II-7 II-47

T2-114 I-5 II-27 II-46 T2-152 I-9 II-7 II-48

T2-115 I-5 II-27 II-47 T2-153 I-9 II-9 II-45

T2-116 I-5 II-27 II-48 T2-154 I-9 II-9 II-46

T2-117 I-5 II-28 II-45 T2-155 I-9 II-9 II-47

T2-118 I-5 II-28 II-46 T2-156 I-9 II-9 II-48

T2-119 I-5 II-28 II-47 T2-157 I-9 11-15 II-45

T2-120 I-5 II-28 II-48 T2-158 I-9 11-15 II-46

T2-121 I-5 II-30 II-45 T2-159 I-9 11-15 II-47

T2-122 I-5 II-30 II-46 T2-160 I-9 11-15 II-48

T2-123 I-5 II-30 II-47 T2-161 I-9 11-21 II-45

T2-124 I-5 II-30 II-48 T2-162 I-9 11-21 II-46

T2-125 I-5 II-33 II-45 T2-163 I-9 11-21 II-47

T2-126 I-5 II-33 II-46 T2-164 I-9 11-21 II-48

T2-127 I-5 II-33 II-47 T2-165 I-9 II-22 II-45

T2-128 I-5 II-33 II-48 T2-166 I-9 II-22 II-46

T2-129 I-5 II-37 II-45 T2-167 I-9 II-22 II-47

T2-130 I-5 II-37 II-46 T2-168 I-9 II-22 II-48

T2-131 I-5 II-37 II-47 T2-169 I-9 II-23 II-45

T2-132 I-5 II-37 II-48 T2-170 I-9 II-23 II-46

T2-133 I-5 II-39 II-45 T2-171 I-9 II-23 II-47

T2-134 I-5 II-39 II-46 T2-172 I-9 II-23 II-48

T2-135 I-5 II-39 II-47 T2-173 I-9 II-24 II-45

T2-136 I-5 II-39 II-48 T2-174 I-9 II-24 II-46

T2-137 I-9 11-1 II-45 T2-175 I-9 II-24 II-47

T2-138 I-9 11-1 II-46 T2-176 I-9 II-24 II-48

T2-139 I-9 11-1 II-47 T2-177 I-9 II-25 II-45

T2-140 I-9 11-1 II-48 T2-178 I-9 II-25 II-46

T2-141 I-9 II-2 II-45 T2-179 I-9 II-25 II-47

T2-142 I-9 II-2 II-46 T2-180 I-9 II-25 II-48

T2-143 I-9 II-2 II-47 T2-181 I-9 II-27 II-45

T2-144 I-9 II-2 II-48 T2-182 I-9 II-27 II-46

T2-145 I-9 II-6 II-45 T2-183 I-9 II-27 II-47

T2-146 I-9 II-6 II-46 T2-184 I-9 II-27 II-48 M C1 C2 C3 M C1 C2 C3

T2-185 I-9 II-28 II-45 T2-223 1-11 II-9 II-47

T2-186 I-9 II-28 II-46 T2-224 1-11 II-9 II-48

T2-187 I-9 II-28 II-47 T2-225 1-11 11-15 II-45

T2-188 I-9 II-28 II-48 T2-226 1-11 11-15 II-46

T2-189 I-9 II-30 II-45 T2-227 1-11 11-15 II-47

T2-190 I-9 II-30 II-46 T2-228 1-11 11-15 II-48

T2-191 I-9 II-30 II-47 T2-229 1-11 11-21 II-45

T2-192 I-9 II-30 II-48 T2-230 1-11 11-21 II-46

T2-193 I-9 II-33 II-45 T2-231 1-11 11-21 II-47

T2-194 I-9 II-33 II-46 T2-232 1-11 11-21 II-48

T2-195 I-9 II-33 II-47 T2-233 1-11 II-22 II-45

T2-196 I-9 II-33 II-48 T2-234 1-11 II-22 II-46

T2-197 I-9 II-37 II-45 T2-235 1-11 II-22 II-47

T2-198 I-9 II-37 II-46 T2-236 1-11 II-22 II-48

T2-199 I-9 II-37 II-47 T2-237 1-11 II-23 II-45

T2-200 I-9 II-37 II-48 T2-238 1-11 II-23 II-46

T2-201 I-9 II-39 II-45 T2-239 1-11 II-23 II-47

T2-202 I-9 II-39 II-46 T2-240 1-11 II-23 II-48

T2-203 I-9 II-39 II-47 T2-241 1-11 II-24 II-45

T2-204 I-9 II-39 II-48 T2-242 1-11 II-24 II-46

T2-205 1-11 11-1 II-45 T2-243 1-11 II-24 II-47

T2-206 1-11 11-1 II-46 T2-244 1-11 II-24 II-48

T2-207 1-11 11-1 II-47 T2-245 1-11 II-25 II-45

T2-208 1-11 11-1 II-48 T2-246 1-11 II-25 II-46

T2-209 1-11 II-2 II-45 T2-247 1-11 II-25 II-47

T2-210 1-11 II-2 II-46 T2-248 1-11 II-25 II-48

T2-211 1-11 II-2 II-47 T2-249 1-11 II-27 II-45

T2-212 1-11 II-2 II-48 T2-250 1-11 II-27 II-46

T2-213 1-11 II-6 II-45 T2-251 1-11 II-27 II-47

T2-214 1-11 II-6 II-46 T2-252 1-11 II-27 II-48

T2-215 1-11 II-6 II-47 T2-253 1-11 II-28 II-45

T2-216 1-11 II-6 II-48 T2-254 1-11 II-28 II-46

T2-217 1-11 II-7 II-45 T2-255 1-11 II-28 II-47

T2-218 1-11 II-7 II-46 T2-256 1-11 II-28 II-48

T2-219 1-11 II-7 II-47 T2-257 1-11 II-30 II-45

T2-220 1-11 II-7 II-48 T2-258 1-11 II-30 II-46

T2-221 1-11 II-9 II-45 T2-259 1-11 II-30 II-47

T2-222 1-11 II-9 II-46 T2-260 1-11 II-30 II-48 M C1 C2 C3 M C1 C2 C3

T2-261 1-1 1 II-33 II-45 T2-268 1-1 1 II-37 II-48

T2-262 1-1 1 II-33 II-46 T2-269 1-1 1 II-39 II-45

T2-263 1-1 1 II-33 II-47 T2-270 1-1 1 II-39 II-46

T2-264 1-1 1 II-33 II-48 T2-271 1-1 1 II-39 II-47

T2-265 1-1 1 II-37 II-45 T2-272 1-1 1 II-39 II-48

T2-266 1-1 1 II-37 II-46

T2-267 1-1 1 II-37 II-47

According to a further embodiment, preference is given to mixtures comprising a component 1 , a component 2 and a component 3, where preference is given in particular to those mixtures in which component 2 is a compound II selected from the group of the following compounds:

II-8 kresoxim-methyl

II-9 pyraclostrobin

II-25 fluxapyroxad

II-26 sedaxane

II-28 fluopyram

II-29 penflufen

II-40 azoxystrobin

11-41 trifloxystrobin

II-42 penthiopyrad

and in which component 3 is a compound II selected from the group of the following compounds:

ll-30a fipronil

ll-32a clothianidin

ll-34a imidacloprid

ll-35a thiamethoxam

Such mixtures according to the invention are listed explicitly in Table T3. According to specific embodiment, these are ternary mixtures comprising, as active compounds, in each case only these three components. Table T3: Mixtures comprising, as component 1 , a preferred compound I, a component 2 selected from the active compounds preferred for component 2 and a component 3 selected from the active compounds preferred for component 3. In the table below, in each case one row of a mixture according to the invention corresponds to the respective mixture components 1 to 3 listed in the row in question. "C" denotes "component", "M" denotes "mixture".

Mixture C 1 C 2 C 3 Mixture C 1 C 2 C 3 Mixture C 1 C 2 C 3 Mixture C 1 C 2 C 3

T3-1 1-1 II-8 ll-30a T3-41 I-5 II-9 ll-30a

T3-2 1-1 II-8 ll-32a T3-42 I-5 II-9 ll-32a

T3-3 1-1 II-8 ll-34a T3-43 I-5 II-9 ll-34a

T3-4 1-1 II-8 ll-35a T3-44 I-5 II-9 ll-35a

T3-5 1-1 II-9 ll-30a T3-45 I-5 II-25 ll-30a

T3-6 1-1 II-9 ll-32a T3-46 I-5 II-25 ll-32a

T3-7 1-1 II-9 ll-34a T3-47 I-5 II-25 ll-34a

T3-8 1-1 II-9 ll-35a T3-48 I-5 II-25 ll-35a

T3-9 1-1 II-25 ll-30a T3-49 I-5 II-26 ll-30a

T3-10 1-1 II-25 ll-32a T3-50 I-5 II-26 ll-32a

T3-1 1 1-1 II-25 ll-34a T3-51 I-5 II-26 ll-34a

T3-12 1-1 II-25 ll-35a T3-52 I-5 II-26 ll-35a

T3-13 1-1 II-26 ll-30a T3-53 I-5 II-28 ll-30a

T3-14 1-1 II-26 ll-32a T3-54 I-5 II-28 ll-32a

T3-15 1-1 II-26 ll-34a T3-55 I-5 II-28 ll-34a

T3-16 1-1 II-26 ll-35a T3-56 I-5 II-28 ll-35a

T3-17 1-1 II-28 ll-30a T3-57 I-5 II-29 ll-30a

T3-18 1-1 II-28 ll-32a T3-58 I-5 II-29 ll-32a

T3-19 1-1 II-28 ll-34a T3-59 I-5 II-29 ll-34a

T3-20 1-1 II-28 ll-35a T3-60 I-5 II-29 ll-35a

T3-21 1-1 II-29 ll-30a T3-61 I-5 II-40 ll-30a

T3-22 1-1 II-29 ll-32a T3-62 I-5 II-40 ll-32a

T3-23 1-1 II-29 ll-34a T3-63 I-5 II-40 ll-34a

T3-24 1-1 II-29 ll-35a T3-64 I-5 II-40 ll-35a

T3-25 1-1 II-40 ll-30a T3-65 I-5 11-41 ll-30a

T3-26 1-1 II-40 ll-32a T3-66 I-5 11-41 ll-32a

T3-27 1-1 II-40 ll-34a T3-67 I-5 11-41 ll-34a

T3-28 1-1 II-40 ll-35a T3-68 I-5 11-41 ll-35a

T3-29 1-1 11-41 ll-30a T3-69 I-5 II-42 ll-30a

T3-30 1-1 11-41 ll-32a T3-70 I-5 II-42 ll-32a

T3-31 1-1 11-41 ll-34a T3-71 I-5 II-42 ll-34a

T3-32 1-1 11-41 ll-35a T3-72 I-5 II-42 ll-35a

T3-33 1-1 II-42 ll-30a T3-73 I-9 II-8 ll-30a

T3-34 1-1 II-42 ll-32a T3-74 I-9 II-8 ll-32a

T3-35 1-1 II-42 ll-34a T3-75 I-9 II-8 ll-34a

T3-36 1-1 II-42 ll-35a T3-76 I-9 II-8 ll-35a

T3-37 I-5 II-8 ll-30a T3-77 I-9 II-9 ll-30a

T3-38 I-5 II-8 ll-32a T3-78 I-9 II-9 ll-32a

T3-39 I-5 II-8 ll-34a T3-79 I-9 II-9 ll-34a

T3-40 I-5 II-8 ll-35a T3-80 I-9 II-9 ll-35a Mixture C 1 C2 C3

T3-114 1-11 II-9 ll-32a

T3-115 1-11 II-9 ll-34a

T3-116 1-11 II-9 ll-35a

T3-117 1-11 II-25 ll-30a

T3-118 1-11 II-25 ll-32a

T3-119 1-11 II-25 ll-34a

T3-120 1-11 II-25 ll-35a

T3-121 1-11 II-26 ll-30a

T3-122 1-11 II-26 ll-32a

T3-123 1-11 II-26 ll-34a

T3-124 1-11 II-26 ll-35a

T3-125 1-11 II-28 ll-30a

T3-126 1-11 II-28 ll-32a

T3-127 1-11 II-28 ll-34a

T3-128 1-11 II-28 ll-35a

T3-129 1-11 II-29 ll-30a

T3-130 1-11 II-29 ll-32a

T3-131 1-11 II-29 ll-34a

T3-132 1-11 II-29 ll-35a

T3-133 1-11 II-40 ll-30a

T3-134 1-11 II-40 ll-32a

T3-135 1-11 II-40 ll-34a

T3-136 1-11 II-40 ll-35a

T3-137 1-11 11-41 ll-30a

T3-138 1-11 11-41 ll-32a

T3-139 1-11 11-41 ll-34a

T3-140 1-11 11-41 ll-35a

T3-141 1-11 II-42 ll-30a

T3-142 1-11 II-42 ll-32a

T3-143 1-11 II-42 ll-34a

T3-144 1-11 II-42 ll-35a

Figure imgf000080_0001

According to a further embodiment, preference is given to mixtures comprising a component 1, a component 2 and a component 3, where preference is given in particular to those mixtures in which component 2 is a compound II selected from the group of the following compounds:

ll-32a clothianidin

ll-34a imidacloprid ll-35a thiamethoxam,

and component 3 is fipronil (compound ll-30a). Such mixtures according to the invention are listed explicitly in Table T4. According to a specific embodiment, these are ternary mixtures comprising, as active compounds, in each case only these three components.

Table T4: Mixtures T4-1 to T4-12 comprising, as component 1 , a preferred compound I and components selected from preferred active compounds II of group I) and fipronil as third component. In the table below, in each case one row corresponds to a mixture according to the invention having the respective mixture components 1 to 3 given in the row in question. "C" denotes "component", "M" denotes "mixture".

Figure imgf000081_0001

According to a further embodiment, preference is given to ternary mixtures comprising a component 1 , a component 2 and a component 3, where preference is given in particular to those mixtures in which component 2 is a compound II selected from the group of the following compounds:

-8 kresoxim-methyl

-9 pyraclostrobin

-25 fluxypyroxad

-26 sedaxane

-28 fluopyram

-29 penflufen

-40 azoxystrobin

-41 trifloxystrobin

-42 penthiopyrad

and component 3 is fipronil (compound ll-30a). Such mixtures are listed explicitly in Table T5 below. According to a specific embodiment, these are ternary mixtures comprising, as active compounds, in each case only these three components.

Table T5: Mixtures comprising, as component 1 , a preferred compound I and components selected from preferred active compounds II of group I) and fipronil as third component. In the table below, in each case one row corresponds to a mixture according to the invention having the respective mixture components 1 to 3 given row in question. "C" denotes "component", "M" denotes "mixture".

Figure imgf000082_0002
Figure imgf000082_0001

Particularly preferred components 4) are com Is II selected from the group of the following compounds:

11-1 epoxiconazole 11-15 fenpropimorph

II-2 metconazole 11-18 mancozeb

11—3 tebuconazole 11-19 metiram

II-6 triticonazole II-20 thiophanate methyl

II-7 prothioconazole 11-21 chlorothalonil

II-8 kresoxim-methyl II-22 metrafenone

II-9 pyraclostrobin II-23 bixafen

11-1 1 dimethomorph II-24 boscalid

11-12 5-ethyl-6-octyl- II-25 N-(3',4',5'-trifluorobiphenyl-2-

[1 ,2,4]triazolo[1 ,5-a]pyrimidin- yl)-3-difluoromethyl-1 -methyl- 7-ylamine 1 H-pyrazole-4-carboxamide

11-13 pyrimethanil II-26 sedaxane

11-14 metalaxyl II-27 isopyrazam 11-28 fluopyram 11-29 penflufen

with the proviso that the components 2), 3) and 4) are different active compounds.

Furthermore, preferred fungicidal components 4 are the following components:

-2 metconazole

-3 tebuconazole

-7 prothioconazole

-9 pyraclostrobin

-15 fenpropimorph

-21 chlorothalonil

-22 metrafenone

-25 fluxapyroxad

-39 difenoconazole

-40 azoxystrobin

In such mixtures, according to one aspect, the active compounds of the formula I are present in the form of a pure enantiomer. According to a further subject matter of the invention, the mixtures according to the invention comprise a diastereomer (consisting of a pair of enantiomers), in the mixtures according to the invention where the enantiomers may be present in any ratio to one another, in particular as a racemic mixture (50:50). According to a further embodiment of the invention, the mixtures according to the invention of Table B comprise a compound I in the form of a mixture of diastereomers. It may be preferred for the compound I to be present in the form of a diastereomer mixture of two diastereomers. Two diastereomers may be present in any ratio to one another. Ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, especially 1 :1 , may be particularly advantageous. The mixture comprises in particular the compounds I-5 and 1-1 1 in the isomer ratios mentioned above.

According to a further embodiment, the invention relates to mixtures comprising a component 1 , a component 2, a component 3 and a component 4 as defined in the following:

Specifically, in mixtures comprising four components, the component 2 is selected from:

-1 epoxiconazole II-24 boscalid

-2 metconazole II-25 fluxapyroxad

-6 triticonazole II-27 isopyrazam

-7 prothioconazole II-28 fluopyram

-9 pyraclostrobin II-30 cyflufenamid

-15 fenpropimorph II-33 proquinazid

-21 chlorothalonil II-37 prochloraz

-22 metrafenone II-39 difenoconazole

-23 bixafen

and the component 3 is selected from: 11-7 prothioconazole II-24 boscalid

11-9 pyraclostrobin II-25 fluxapyroxad

11-15 fenpropimorph II-30 cyflufenamid

11-21 chlorothalonil II-37 prochloraz

II-22 metrafenone II-39 difenoconazole and the component 4 is selected from

II-9 pyraclostrobin

11-15 fenpropimorph

11-21 chlorothalonil

According to a further embodiment of the invention, preference is given to mixtures comprising four components (1 , 2, 3 and 4) in which component 2 is selected from the group of the following compounds:

-8 kresoxim-methyl

-9 pyraclostrobin

-25 fluxapyroxad

-26 sedaxane

-28 fluopyram

-29 penflufen

-40 azoxystrobin

-41 trifloxystrobin

-42 penthiopyrad 5 and in which component 3 is a compound II selected from the group of the

following compounds:

ll-32a clothianidin

ll-34a imidacloprid

ll-35a thiamethoxan

0 and in which component 4 is fipronil (ll-30a).

Such mixtures are listed explicitly in Table Qll below:

Table Qll: Mixtures QII-1 to QII-54 comprising, as component 1 , a preferred compound I, a preferred component 2, a preferred component 3 of group I) and fipronil as component 4. In the table below, in each case one row corresponds to a mixture according to the invention having the respective mixture components 1 to 4 listed in the row in question. "C" denotes "component", "M" denotes "mixture".

Figure imgf000084_0001
M C1 C2 C3 C4 M C1 C2 C3 C4

QII.1-3 1-1 II-8 ll-35a ll-30a QII.1-42 I-5 II-28 ll-35a ll-30a

QII.1-4 1-1 II-9 ll-32a ll-30a QII.1-43 I-5 II-29 ll-32a ll-30a

QII.1-5 1-1 II-9 ll-34a ll-30a QII.1-44 I-5 II-29 ll-34a ll-30a

QII.1-6 1-1 II-9 ll-35a ll-30a QII.1-45 I-5 II-29 ll-35a ll-30a

QII.1-7 1-1 II-25 ll-32a ll-30a QII.1-46 I-5 II-40 ll-32a ll-30a

QII.1-8 1-1 II-25 ll-34a ll-30a QII.1-47 I-5 II-40 ll-34a ll-30a

QII.1-9 1-1 II-25 ll-35a ll-30a QII.1-48 I-5 II-40 ll-35a ll-30a

QII.1-10 1-1 II-26 ll-32a ll-30a QII.1-49 I-5 11-41 ll-32a ll-30a

QII.1-11 1-1 II-26 ll-34a ll-30a QII.1-50 I-5 11-41 ll-34a ll-30a

QII.1-12 1-1 II-26 ll-35a ll-30a QII.1-51 I-5 11-41 ll-35a ll-30a

QII.1-13 1-1 II-28 ll-32a ll-30a QII.1-52 I-5 II-42 ll-32a ll-30a

QII.1-14 1-1 II-28 ll-34a ll-30a QII.1-53 I-5 II-42 ll-34a ll-30a

QII.1-15 1-1 II-28 ll-35a ll-30a QII.1-54 I-5 II-42 ll-35a ll-30a

QII.1-16 1-1 II-29 ll-32a ll-30a QII.1-55 I-9 II-8 ll-32a ll-30a

QII.1-17 1-1 II-29 ll-34a ll-30a QII.1-56 I-9 II-8 ll-34a ll-30a

QII.1-18 1-1 II-29 ll-35a ll-30a QII.1-57 I-9 II-8 ll-35a ll-30a

QII.1-19 1-1 II-40 ll-32a ll-30a QII.1-58 I-9 II-9 ll-32a ll-30a

QII.1-20 1-1 II-40 ll-34a ll-30a QII.1-59 I-9 II-9 ll-34a ll-30a

QII.1-21 1-1 II-40 ll-35a ll-30a QII.1-60 I-9 II-9 ll-35a ll-30a

QII.1-22 1-1 11-41 ll-32a ll-30a QII.1-61 I-9 II-25 ll-32a ll-30a

QII.1-23 1-1 11-41 ll-34a ll-30a QII.1-62 I-9 II-25 ll-34a ll-30a

QII.1-24 1-1 11-41 ll-35a ll-30a QII.1-63 I-9 II-25 ll-35a ll-30a

QII.1-25 1-1 II-42 ll-32a ll-30a QII.1-64 I-9 II-26 ll-32a ll-30a

QII.1-26 1-1 II-42 ll-34a ll-30a QII.1-65 I-9 II-26 ll-34a ll-30a

QII.1-27 1-1 II-42 ll-35a ll-30a QII.1-66 I-9 II-26 ll-35a ll-30a

QII.1-28 I-5 II-8 ll-32a ll-30a QII.1-67 I-9 II-28 ll-32a ll-30a

QII.1-29 I-5 II-8 ll-34a ll-30a QII.1-68 I-9 II-28 ll-34a ll-30a

QII.1-30 I-5 II-8 ll-35a ll-30a QII.1-69 I-9 II-28 ll-35a ll-30a

QII.1-31 I-5 II-9 ll-32a ll-30a QII.1-70 I-9 II-29 ll-32a ll-30a

QII.1-32 I-5 II-9 ll-34a ll-30a QII.1-71 I-9 II-29 ll-34a ll-30a

QII.1-33 I-5 II-9 ll-35a ll-30a QII.1-72 I-9 II-29 ll-35a ll-30a

QII.1-34 I-5 II-25 ll-32a ll-30a QII.1-73 I-9 II-40 ll-32a ll-30a

QII.1-35 I-5 II-25 ll-34a ll-30a QII.1-74 I-9 II-40 ll-34a ll-30a

QII.1-36 I-5 II-25 ll-35a ll-30a QII.1-75 I-9 II-40 ll-35a ll-30a

QII.1-37 I-5 II-26 ll-32a ll-30a QII.1-76 I-9 11-41 ll-32a ll-30a

QII.1-38 I-5 II-26 ll-34a ll-30a QII.1-77 I-9 11-41 ll-34a ll-30a

QII.1-39 I-5 II-26 ll-35a ll-30a QII.1-78 I-9 11-41 ll-35a ll-30a

QII.1-40 I-5 II-28 ll-32a ll-30a QII.1-79 I-9 II-42 ll-32a ll-30a

QII.1-41 I-5 II-28 ll-34a ll-30a QII.1-80 I-9 II-42 ll-34a ll-30a M C1 C2 C3 C4 M C1 C2 C3 C4

QII.1-81 I-9 II-42 ll-35a ll-30a QII.1-96 1-1 1 II-28 ll-35a ll-30a

QII.1-82 1-1 1 II-8 ll-32a ll-30a QII.1-97 1-1 1 II-29 ll-32a ll-30a

QII.1-83 1-1 1 II-8 ll-34a ll-30a QII.1-98 1-1 1 II-29 ll-34a ll-30a

QII.1-84 1-1 1 II-8 ll-35a ll-30a QII.1-99 1-1 1 II-29 ll-35a ll-30a

QII.1-85 1-1 1 II-9 ll-32a ll-30a Qll.1-100 I _ Λ A II-40 ll-32a ll-30a

QII.1-86 1-1 1 II-9 ll-34a ll-30a QII.1-101 1-1 1 II-40 ll-34a ll-30a

QII.1-87 1-1 1 II-9 ll-35a ll-30a Qll.1-102 II-40 ll-35a ll-30a

QII.1-88 1-1 1 II-25 ll-32a ll-30a Qll.1-103 11-41 ll-32a ll-30a

QII.1-89 1-1 1 II-25 ll-34a ll-30a Qll.1-104 11-41 ll-34a ll-30a

QII.1-90 1-1 1 II-25 ll-35a ll-30a Qll.1-105 I - Ί Ί 11-41 ll-35a ll-30a

QII.1-91 1-1 1 II-26 ll-32a ll-30a Qll.1-106 II-42 ll-32a ll-30a

QII.1-92 1-1 1 II-26 ll-34a ll-30a Qll.1-107 II-42 ll-34a ll-30a

QII.1-93 1-1 1 II-26 ll-35a ll-30a Qll.1-108 1—1 Ί II-42 ll-35a ll-30a

QII.1-94 1-1 1 II-28 ll-32a ll-30a

QII.1-95 1-1 1 II-28 ll-34a ll-30a

The mixtures according to the invention of the compounds I and II and the compositions according to the invention thereof are suitable as fungicides for controlling harmful fungi. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi including soilborne pathogens which originate in particular from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some of them are systemically active and can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. In addition, they are suitable for controlling fungi which, inter alia, attack the wood or the roots of plants.

The mixtures according to the invention and the compositions according to the invention are of particular importance for the control of a large number of pathogenic fungi on various crop plants such as cereals, for example wheat, rye, barley, triticale, oats or rice; beets, for example sugar beets or fodder beets; pomaceous fruits, stone fruits and soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; leguminous plants, for example beans, lentils, peas, lucerne or soybeans; oil plants, for example oilseed rape, mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palms, peanuts or soybeans; cucurbits, for example pumpkins, cucumbers or melons; fiber plants, for example cotton, flax, hemp or jute; citrus fruits, for example oranges, lemons, grapefruits or mandarins; vegetable plants, for example spinach, lettuce, asparagus, cabbage plants, carrots, onions, tomatoes, potatoes, pumpkins or bell peppers; laurel plants, for example avocados, cinnamon or camphor; energy and raw material plants, for example corn, soybeans, wheat, oilseed rape, sugar cane or oil palms; corn; tobacco; nuts; coffee; tea; bananas; grapevines (grapes for eating and grapes for wine making); hops; grass, for example lawns; rubber plants; ornamental and forest plants, for example flowers, shrubs, deciduous trees and coniferous trees, and also on the propagation material, for example seeds, and on the harvested products of these plants.

Preferably, the mixtures and compositions according to the invention are used for controlling a large number of fungal pathogens in agricultural crops, for example potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, oilseed rape, leguminous plants, sunflowers, coffee or sugar cane; fruit plants, grapevines and ornamental plants and vegetable plants, for example cucumbers, tomatoes, beans and pumpkins and also on the propagation material, for example seeds, and the harvested products of these plants.

The term plant propagation materials comprises all generative parts of the plant, for example seeds, and vegetative plant parts, such as seedlings and tubers (for example potatoes) which can be utilized for propagating a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts including seedlings and young plants which are transplanted after germination or after emergence. The young plants can be protected by partial or complete treatment, for example by immersion or watering, against harmful fungi.

The treatment of plant propagation materials with mixtures or compositions according to the invention is used for controlling a large number of fungal pathogens in cereal crops, for example wheat, rye, barley or oats; rice, corn, cotton and soybeans.

The term crop plants also includes those plants which have been modified by breeding, mutagenesis or genetic engineering methods including the biotechnological agricultural products which are on the market or under development (see, for example, http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or by natural recombination (that is to say, a recombination of the genetic information). In general, one or more genes are integrated into the genetic material of the plant in order to improve the properties of the plant. Such modifications by genetic engineering include post-translational

modifications of proteins, oligopeptides or polypeptides, for example by glycosylation or attachment of polymers such as, for example, prenylated, acetylated or farnesylated radicals or PEG radicals.

By way of example, mention may be made of plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (for example US 6,222,100, WO 01/82685, WO 00/26390, WO

97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as, for example, glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A 242 236, EP-A 242 246) or oxynil herbicides (see, for example, US 5,559,024). Clearfield® oilseed rape (BASF SE, Germany), for example, which is tolerant to imidazolinones, for example imazamox, was generated by breeding and mutagenesis. With the aid of genetic engineering methods, crop plants such as soybeans, cotton, corn, beets and oilseed rape were generated which are resistant to glyphosate or glufosinate, and which are obtainable under the trade names

RoundupReady® (glyphosate-resistant, Monsanto, U.S.A.) and Liberty Link®

(glufosinate-resistant, Bayer CropScience, Germany).

Also included are plants which, owing to interventions by genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insecticidal proteins (VI Ps), for example VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from

Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3- hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdyson inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase;

receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pretoxins, hybrid proteins or 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 disclosed 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. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Many of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties which produce the toxin Cry1 Ab), YieldGard® Plus (corn varieties which produce the toxins CrylAb and Cry3Bb1 ), Starlink® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin CrylAc), Bollgard® I (cotton varieties which produce the toxin CrylAc), Bollgard® II (cotton varieties which produce the toxins CrylAc and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin);

NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin CrylAb and the PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1 ), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cryl F and the PAT enzyme).

Also included are plants which, with the aid of genetic engineering, produce one or more proteins which have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see

EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato

Solanum bulbocastanum) or T4 lysozyme (for example potato varieties which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).

Also included are plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example 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.

Also included are plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsaturated omega 9 fatty acids (for example Nexera® oilseed rape, DOW Agro Sciences, Canada).

Also included are plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato, BASF SE, Germany). Specifically, the mixtures and compositions according to the invention are suitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamental plants, vegetable crops (for example A. Candida) and sunflowers (for example A. tragopogonis); Alternaria spp. (black spot disease, black blotch) on vegetables, oilseed rape (for example A. brassicola or A. brassicae), sugar beet (for example A. tenuis), fruit, rice, soybeans and also on potatoes (for example A. solani or A. alternata) and tomatoes (for example A. solani or A. alternata) and Alternaria spp. (black head) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, for example A. tritici (Ascochyta leaf blight) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), for example leaf spot diseases (for example D.maydis and B.zeicola) on corn, for example glume blotch (B. sorokiniana) on cereals and for example B. oryzae on rice and on lawn; Blumeria (old name: Erysiphe) graminis (powdery mildew) on cereals (for example wheat or barley); Botryosphaeria spp.

('Black Dead Arm Disease') on grapevines (for example B. obtusa); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold, gray rot) on soft fruit and pomaceous fruit (inter alia strawberries), vegetables (inter alia lettuce, carrots, celeriac and cabbage), oilseed rape, flowers, grapevines, forest crops and wheat (ear mold); Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (blue stain fungus) on deciduous trees and coniferous trees, for example C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spot) on corn (for example C. zeae-maydis), rice, sugar beets (for example C. beticola), sugar cane, vegetables, coffee, soybeans (for example C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomato (for example C. fulvum: tomato leaf mold) and cereals, for example C.

herbarum (ear rot) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium or Bipolaris) spp. (leaf spot) on corn (for example C. carbonum), cereals (for example C. sativus, anamorph: B. sorokiniana: glume blotch) and rice (for example C. miyabeanus, anamorph: H. oryzae); Colletotrichum

(teleomorph: Glomerella) spp. (anthracnosis) on cotton (for example C. gossypii), corn (for example C. graminicola: stem rot and anthracnosis), soft fruit, potatoes (for example C. coccodes: wilt disease), beans (for example C. lindemuthianum) and soybeans (for example C. truncatum); Corticium spp., for example C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spot) on soybeans and ornamental plants; Cycloconium spp., for example C. oleaginum on olive; Cylindrocarpon spp. (for example fruit tree cancer or black foot disease of grapevine, teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (for example C. liriodendri, teleomorph:

Neonectria liriodendri, (black foot disease)) and many ornamental trees; Dematophora (teleomorph: Rosellinia) necatrix (root/stem rot) on soybeans; Diaporthe spp.) for example D. phaseolorum (stem disease) on soybeans; Drechslera (syn.

Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (for example D. teres, net blotch) and on wheat (for example D. tritici-repentis: DTR leaf spot), rice and lawn; Esca disease (dieback of grapevine, apoplexia) on grapevines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (old name Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruit (£. pyri) and soft fruit (£. veneta: anthracnosis) and also grapevines (£. ampelina: anthracnosis ;

Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black head) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (£. betae), vegetables (for example E. pisi), such as cucumber species (for example E. cichoracearum) and cabbage species, such as oilseed rape (for example E. cruciferarum); Eutypa lata (Eutypa cancer or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, grapevines and many ornamental trees; Exserohilum (syn. Helminthosporium) spp. on corn (for example E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt disease, root and stem rot) on various plants, such as for example F. graminearum or F culmorum (root rot and silver-top) on cereals (for example wheat or barley), F oxysporum on tomatoes, F. solani on soybeans and F verticillioides on corn; Gaeumannomyces graminis (take- all) on cereals (for example wheat or barley) and corn; Gibberella spp. on cereals (for example G. zeae) and rice (for example G. fujikuroi: bakanae disease); Glomerella cingulata on grapevines, pomaceous fruit and other plants and G. gossypii on cotton; grainstaining complex on rice; Guignardia bidwellii (black rot) on grapevines;

Gymnosporangium spp. on Rosaceae and juniper, for example G. sabinae (pear rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., for example H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on grapevines; Macrophomina phaseolina (syn. phaseoli) (root/stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (for example wheat or barley);

Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., for example M. laxa, M. fructicola and M. fructigena (blossom and twig blight) on stone fruit and other Rosaceae; Mycosphaerella spp. on cereals, bananas, soft fruit and peanuts, such as for example M. graminicola (anamorph: Septoria tritici, Septoria leaf blotch) on wheat or M. fijiensis (sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (for example P. brassicae), oilseed rape (for example P. parasitica), bulbous plants (for example P. destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp., for example on grapevines (for example P. tracheiphila and P.

tetraspora) and soybeans (for example P. gregata: stem disease); Phoma lingam (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spot) on sugar beets; Phomopsis spp. on sunflowers, grapevines (for example P. viticola: dead-arm disease) and soybeans (for example stem canker/stem blight: P. phaseoli, teleomorph:

Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn; Phytophthora spp. (wilt disease, root, leaf, stem and fruit rot) on various plants, such as on bell peppers and cucumber species (for example P. capsici), soybeans (for example P.

megasperma, syn. P. sojae), potatoes and tomatoes (for example P. infestans: late blight and brown rot) and deciduous trees (for example P. ramorum: sudden oak death); Plasmodiophora brassicae (club-root) on cabbage, oilseed rape, radish and other plants; Plasmopara spp., for example P. viticola (peronospora of grapevines, downy mildew) on grapevines and P. halstedii on sunflowers; Podosphaera spp.

(powdery mildew) on Rosaceae, hops, pomaceous fruit and soft fruit, for example P. leucotricha on apple; Polymyxa spp., for example on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides (eyespot/stem break, teleomorph: Tapesia yallundae) on cereals, for example wheat or barley; Pseudoperonospora (downy mildew) on various plants, for example P. cubensis on cucumber species or P. humili on hops; Pseudopezicula tracheiphila (angular leaf scorch, anamorph: Phialophora) on grapevines; Puccinia spp. (rust disease) on various plants, for example P. triticina (brown rust of wheat), P. striiformis (yellow rust), P. hordei (dwarf leaf rust), P. graminis (black rust) or P. recondita (brown rust of rye) on cereals, such as for example wheat, barley or rye, and on asparagus (for example P. asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (speckled leaf blotch) on wheat or P. feres (net blotch) on barley; Pyricularia spp., for example P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on lawn and cereals; Pythium spp. (damping-off disease) on lawn, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beets, vegetables and other plants (for example P. ultimum or P. aphanidermatum); Ramularia spp., for example R. collo-cygni (Ramularia leaf and lawn spot/physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables and on various other plants, for example R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (sharp eyespot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevines 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 vegetable and field crops, such as oilseed rape, sunflowers (for example Sclerotinia sclerotiorum) and soybeans (for example S. rolfsii); Septoria spp. on various plants, for example S. glycines (leaf spot) on soybeans, S. tritici (Septoria leaf blotch) on wheat and S. (syn. Stagonospora) nodorum (leaf blotch and glume blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on grapevines; Setospaeria spp. (leaf spot) on corn (for example S. turcicum, syn. Helminthosporium turcicum) and lawn; Sphacelotheca spp. (head smut) on corn, (for example S. reiliana: kernel smut), millet and sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucumber species; Spongospora subterranea (powdery scab) on potatoes and the viral diseases transmitted thereby; Stagonospora spp. on cereals, for example S. nodorum (leaf blotch and glume blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., for example

T. deformans (curly-leaf disease) on peach and T. pruni (plum-pocket disease) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, for example T. basicola (syn. Chalara elegans); Tilletia spp. (bunt or stinking smut) on cereals, such as for example T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (gray snow mold) on barley or wheat; Urocystis spp., for example U. occulta (flag smut) on rye; Uromyces spp. (rust) on vegetable plants, such as beans (for example U. appendiculatus, syn. U. phaseoli) and sugar beets (for example U. betae); Ustilago spp. (loose smut) on cereals (for example U. nuda and U. avaenae), corn (for example U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (for example V. inaequalis) and pears; and Verticillium spp. (leaf and shoot wilt) on various plants, such as fruit trees and ornamental trees, grapevines, soft fruit, vegetable and field crops, such as for example V. dahliae on strawberries, oilseed rape, potatoes and tomatoes.

Moreover, the mixtures and compositions according to the invention are suitable for controlling harmful fungi in the protection of stored products (and of harvested products) and in the protection of materials and buildings. The term "protection of materials and buildings" encompasses the protection of industrial and non-living materials such as, for example, adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastic, cooling lubricants, fibers and tissues, against attack and destruction by unwanted microorganisms such as fungi and bacteria. In the protection of wood and materials, 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., and in addition in the protection of materials to the following yeast fungi: Candida spp. and Saccharomyces cerevisae.

The compounds of the formula I, and also those of the formula II, may be present in various crystal modifications which may differ in their biological activity. Their mixtures are included in the scope of the present invention.

The mixtures and compositions according to the invention are suitable for improving plant health. Moreover, the invention relates to a method for improving plant health by treating the plants, the plant propagation material and/or the site at which the plants grow or are intended to grow with an effective amount of the compounds I or the compositions according to the invention.

The term "plant health" comprises those states of a plant and/or its harvested material which are determined by various indicators individually or in combination, such as, for example, yield (for example increased biomass and/or increased content of utilizable ingredients), plant vitality (for example increased plant growth and/or greener leaves ("greening effect")), quality (for example increased content or composition of certain ingredients) and tolerance to biotic and/or abiotic stress. The indicators mentioned here for a state of plant health may occur independently of one another or may influence each other.

The mixtures according to the invention are employed as such or in the form of a composition by treating the harmful fungi, their habitat or the plants or plant propagation materials, for example seed materials, to be protected from fungal attack, for example seed, the soil, areas, materials or spaces with a fungicidally effective amount of the mixture according to the invention. The application can be carried out both before and after the infection of the plants, plant propagation materials, for example seed materials, the soil, the areas, materials or spaces by the fungi.

Plant propagation materials can be treated prophylactically during or even before sowing or during or even before transplanting with the mixtures according to the invention or a composition thereof (a composition comprising at least one compound I and at least one compound II, preferably one or two compounds II).

The invention furthermore relates to agrochemical compositions comprising a solvent or solid carrier and the mixture according to the invention, and also to their use for controlling harmful fungi.

In this context, the term "preparation" has the same meaning as "composition", in particular "agrochemical composition", and "formulation".

An agrochemical composition comprises a fungicidally effective amount of the mixture according to the invention. The term "effective amount" refers to an amount of the agrochemical composition or of the 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 cause any significant damage to the treated crop plants. Such an amount may vary within a wide range and is influenced by numerous factors, such as, for example, the harmful fungus to be controlled, the respective crop plant or materials treated, the climatic conditions and compounds.

The compounds I and the one or more compounds II can be applied simultaneously, that is jointly or separately, or in succession, the order, in the case of separate application, generally not having any effect on the control results. The method for controlling harmful fungi is carried out by separate or joint application of the compound I and the compound(s) II or of mixtures of the compound I and the compound(s) II by spraying or dusting the seed, the plants or the soil before or after sowing of the plants or before or after emergence of the plants. The compounds I and II may be present in a joint composition or in separate compositions. Here, type and preparation of the composition in question corresponds to type and preparation as described here in a general manner for compositions.

The compounds I and the compounds II, and also their N-oxides and salts and their mixtures, can be converted into the types customary for agrochemical compositions, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type of composition depends on the respective intended purpose; in each case, it should ensure a fine and even distribution of the compounds of the mixtures according to the invention.

Here, examples of types of compositions 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 either be water-soluble or -dispersible (wettable), and also gels for treating plant propagation materials such as seed (GF).

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

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 edition, McGraw-Hill, New York, 1963, 8-57 and ff., 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 may furthermore also comprise auxiliaries customary for crop protection compositions, the selection of the auxiliaries depending on the specific use form or the active compound.

Examples of suitable auxiliaries are solvents, solid carriers, surfactants (such as further solubilizers, protective colloids, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and adhesives (for example for the treatment of seed).

Suitable solvents are water, organic solvents, such as mineral oil fractions having a medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils, and also oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones, such as cyclohexanone, gamma-butyrolactone, dimethyl fatty amides, fatty acids and fatty acid esters and strongly polar solvents, for example amines, such as N-methylpyrrolidone. In principle, it is also possible to use solvent mixtures, and also mixtures of the solvents mentioned above and water.

Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, bark dust, sawdust, nutshell meal, cellulose powder or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants or emulsifiers) are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example of lignosulfonic acid (Borresperse® types, Borregaard, Norway), phenolsulfonic acid, naphthalenesulfonic acid (Morwet® types, Akzo Nobel, USA) and dibutylnaphthalenesulfonic acid (Nekal® types, BASF, Germany), and also of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylated

isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or

polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors, and also proteins, denatured proteins, polysaccharides (for example methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol® types, Clariant, Switzerland), polycarboxylates (Sokalan® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin® types, BASF, Germany), polyethyleneimine (Lupasol® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.

Examples of thickeners (i.e. compounds which impart modified flow properties to the composition, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides and also organic and inorganic sheet minerals, such as xanthan gum (Kelzan®, CP Kelco, USA), Rhodopol® 23 (Rhodia, France) or Veegum® (R.T.

Vanderbilt, USA) or Attaclay® (Engelhard Corp., NJ, USA).

Bactericides can be added for stabilizing the composition. Examples of bactericides are bactericides based on dichlorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones (Acticide® MBS from Thor Chemie). Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

Examples of antifoams 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 colors are both pigments, which are sparingly soluble in water, and dyes, which are soluble in water. Examples which may be mentioned are the dyes and pigments known under the names Rhodamin 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.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose ether (Tylose®, Shin-Etsu, Japan).

Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydro- naphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the compounds I and the further active compounds II with at least one solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to at least one solid carrier. Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic substances, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal meal, tree bark meal, sawdust and nutshell meal, cellulose powder or other solid carriers.

The following are examples of types of composition:

1 . Types of composition for dilution with water

i) Water-soluble concentrates (SL, LS)

10 parts by weight of the active compounds are dissolved with 90 parts by weight of water or with a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water. This gives a composition having an active compound content of 10% by weight.

ii) Dispersible concentrates (DC)

20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound 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 with water gives an emulsion. The composition has an active compound content of 15% by weight.

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 to 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active compound content of 25% by weight.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compounds are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the composition is 20% by weight.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50 parts by weight of the active compounds are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water- soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The composition has an active compound content of 50% by weight.

vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of the active compounds are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the composition is 75% by weight.

viii) Gels (GF)

20 parts by weight of the active compounds, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground in a ball mill to give a fine suspension. Dilution with water gives a stable suspension with an active compound content of 20% by weight.

2. Types of composition to be applied undiluted

ix) Dusts (DP, DS)

5 parts by weight of the active compounds are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product with an active compound content of 5% by weight.

x) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compounds is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules with an active compound content of 0.5% by weight to be applied undiluted.

xi) ULV solutions (UL)

10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a composition with an active compound content of 10% by weight to be applied undiluted.

In general, the compositions of the mixtures according to the invention comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I and II or their mixtures. The compounds I and II are preferably employed in a purity of from 90% to 100%, preferably from 95% to 100% (NMR spectrum).

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

For seed treatment, preference is given to using suspensions. Such compositions usually comprise from 1 to 800 g of active compound/I, from 1 to 200 g of surfactants/I, from 0 to 200 g of antifreeze agents/I, from 0 to 400 g of binders/I, from 0 to 200 g of colorants/l 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 example in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading, raking in, immersing or pouring. The types of composition depend entirely on the intended purposes; the intention is to ensure in each case the finest possible distribution of the active compounds or active compound mixtures according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.

The active compounds may also be used successfully in the ultra-low-volume process (ULV), by which it is possible to apply compositions comprising over 95% by weight of active compound, or even to apply the active compound without additives. When used in crop protection, the application rates are from 0.001 to 2.0 kg of active compound per ha, preferably from 0.005 to 2 kg per ha, particularly preferably from 0.05 to 0.9 kg per ha, especially from 0.1 to 0.75 kg per ha, depending on the nature of the desired effect.

In the treatment of plant propagation materials, for example seed, the amounts of active compound (or amounts of active compound mixtures) used are generally from 0.1 to 1000 g/100 kg of propagation material or seed, preferably from 1 to 1000 g/100 kg, particularly preferably from 1 to 100 g/100 kg, especially from 5 to 100 g/100 kg.

When used in the protection of materials or stored products, the amount of active compound or active compound mixture applied depends on the kind of application area and on the desired effect. Amounts typically applied in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of treated material.

Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the active compounds or active compound mixtures or the compositions comprising them, optionally not until immediately prior to use (tank mix). These compositions can be admixed with the compositions according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1 .

The following are particularly suitable as adjuvants in this context: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus® 245, Atplus® MBA 1303, Plurafac® LF 300 and Lutensol® ON 30; EO- PO block polymers, for example Pluronic® RPE 2035 and Genapol® B; alcohol ethoxylates, for example Lutensol® XP 80; and sodium dioctylsulfosuccinate, for example Leophen® RA.

Further preferred specific embodiments of the present invention are illustrated in more detail below:

According to a preferred embodiment, the component 2) used is an active compound selected from the group consisting of pyraclostrobin, fluxapyroxad, fenpropimorph, prothioconazole and chlorothalonil and/or agriculturally acceptable salts thereof in a weight ratio of from 20:1 to 1 :20 (component 1 : component 2), where component 1 is preferably compound 1-1 1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, I- 1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . These mixtures are in particular binary mixtures, i.e. compositions according to the invention comprising compound 1-1 1 (component 1 ) and a further active compound (component 2) as active compounds, component 2 being selected from the group consisting of pyraclostrobin, fluxapyroxad, fenpropimorph, prothioconazole and chlorothalonil in a weight ratio of from 1 :20 to 20:1 , particularly preferably in the range from 1 :10 to 10:1 , especially in the range from 1 :3 to 3:1. It may also be preferable that the weight ratio is in the range of from 1 :2 to 2:1. "Binary mixture" in the context of the present invention means that only two active compounds are present. The mixture may, of course, comprise any kind of additive or the like as described herein in more detail to provide a formulation suitable for use in agriculture.

According to a further specific embodiment, the present invention relates to the binary mixture comprising 1-1 1 and fluxapyroxad in a weight ratio of from 20:1 to 1 :20, specifically from 5:1 to 1 :5, in particular from 3:1 to 1 :3, more specifically from 2:1 to 1 :2. Surprisingly, this mixture shows synergistic effects and according to the invention the components are employed in particular in synergistically effective amounts.

According to a further specific embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 , and fluxapyroxad for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above. This mixture is particularly suitable for controlling wheat pathogens. The mixture is particularly suitable for controlling wheat pathogens selected from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. The mixture is furthermore useful for controlling pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

This mixture is furthermore suitable for controlling barley pathogens. This mixture is suitable in particular for controlling barley pathogens selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens, in particular selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling soybean pathogens. This mixture is suitable in particular for controlling soybean pathogens selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used advantageously for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling corn pathogens. This mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling sugar beet pathogens. This mixture is suitable in particular for controlling sugar beet pathogens selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae. According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fluxapyroxad for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

The mixture of compound 1-1 1 and fluxapyroxad is also suitable for controlling pathogens in special crops such as, for example, lawn, potato, tomato, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled in accordance with the present invention are preferably selected from the group consisting of Sclerotinia homeocarpa and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternate and

Rhizoctonia solani. A cucurbit pathogen which can be controlled in accordance with the present invention is in particular Sphaerotheca fuliginea. Grapevine pathogens which can be controlled in accordance with the present invention are in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled in accordance with the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to a further specific embodiment, the present invention relates to the binary mixture of compound 1-1 1 and pyraclostrobin in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 3:1 to 1 :3, even more specifically from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and I- 1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to one embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above and where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1.

This mixture is suitable in particular for controlling wheat pathogensThis mixture is suitable in particular for controlling wheat pathogens selected from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. This mixture is furthermore useful for controlling pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. This mixture is furthermore suitable for controlling barley pathogens. This mixture is suitable in particular for controlling barley pathogens selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens, in particular selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling soybean pathogens.. This mixture is suitable in particular for controlling soybean pathogens selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling corn pathogens. This mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling sugar beet pathogens. This mixture is suitable in particular for controlling sugar beet pathogens selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and pyraclostrobin for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

The mixture of compound 1-1 1 and pyraclostrobin is also suitable for controlling pathogens in special crops such as, for example, lawn, potato, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled in accordance with the present invention are selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled in accordance with the present invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled in accordance with the present invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled in accordance with the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to a further embodiment, the present invention relates to the binary mixture of compound 1-1 1 and fenpropimorph in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 3:1 to 1 :3, more specifically from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in

synergistically effective amounts.

According to one embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

This mixture is suitable in particular for controlling wheat pathogens. This mixture is suitable in particular for controlling wheat pathogens selected from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. This mixture is furthermore suitable for controlling pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

This mixture is furthermore suitable for controlling barley pathogens. This mixture is suitable in particular for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens, in particular selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides. According to a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling soybean pathogens. This mixture is suitable in particular for controlling soybean pathogens selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp.. According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling corn pathogens. This mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling sugar beet pathogens. This mixture is suitable in particular for controlling sugar beet pathogens selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and fenpropimorph for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

The binary mixture of compound 1-1 1 and fenpropimorph is also suitable for controlling pathogens in special crops such as, for example, lawn, potato, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled in accordance with the present invention are selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and

Rhizoctonia solani. A cucurbit pathogen which can be controlled in accordance with the present invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled in accordance with the present invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled in accordance with the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola. According to a further embodiment, the present invention relates to the binary mixture of compound 1-1 1 and prothioconazole in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 3:1 to 1 :3, more specifically from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in

synergistically effective amounts. According to one embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

This mixture is suitable in particular for controlling wheat pathogens. This mixture is suitable in particular for controlling wheat pathogens selected from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. This mixture is furthermore suitable for controlling pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

This mixture is furthermore suitable for controlling barley pathogens. This mixture is suitable in particular for controlling barley pathogens selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens, in particular selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling soybean pathogens. This mixture is suitable in particular for controlling soybean pathogens selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling corn

pathogensThis mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and

Helminthosporium maydis. According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling sugar beet pathogens. This mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and prothioconazole for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

The binary mixture of compound 1-1 1 and prothioconazole is also suitable for controlling pathogens in special crops such as, for example, lawn, potato, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled in accordance with the present invention are selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled in accordance with the present invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled in accordance with the present invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled in accordance with the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to a further embodiment, the present invention relates to the binary mixture of compound 1-1 1 and chlorothalonil in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 3:1 to 1 :3, more specifically from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in

synergistically effective amounts.

According to one embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling cereal pathogens, where the components are employed in the mixing ratios mentioned above, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 .

This mixture is suitable in particular for controlling wheat pathogens. This mixture is suitable in particular for controlling wheat pathogens selected from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. Furthermore, said mixture is useful for controlling pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

This mixture is furthermore suitable for controlling barley pathogens. This mixture is suitable in particular for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens, in particular selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling soybean pathogens. This mixture is suitable in particular for controlling soybean pathogens selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp.. According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling corn pathogens. This mixture is suitable in particular for controlling corn pathogens selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling sugar beet pathogens. This mixture is suitable in particular for controlling sugar beet pathogens selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to yet a further embodiment, the present invention relates to the use of the binary mixture of compound 1-1 1 and chlorothalonil for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

The binary mixture of compound 1-1 1 and chlorothalonil is also suitable for controlling pathogens in special crops such as, for example, lawn, potato, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled in accordance with the present invention are selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and

Rhizoctonia solani. A cucurbit pathogen which can be controlled in accordance with the present invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled in accordance with the present invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled in accordance with the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to a further specific embodiment of the invention, the specific mixtures are ternary mixtures, i.e. compositions according to the invention comprising, as active compounds, compound 1-1 1 , a second active compound (component 2) and a third active compound (component 3). Component 2 is a) fluxapyroxad or b) prothioconazole and component 3 is, if component 2 is fluxapyroxad, selected from the group consisting of a) pyraclostrobin and fenpropimorph; and, if component 2 is prothioconazole, selected from the group consisting of b) fluxapyroxad, bixafen, pyraclostrobin, dimoxystrobin, picoxystrobin, fluoxastrobin, fluopyram and penflufen. According to one aspect, compound 1-1 1 is present as isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d , in each case individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1.

"Ternary mixture" in the context of the present invention means that exactly three active compounds are present. The mixture may, of course, comprise any kind of additive or the like as described herein in more detail to provide a formulation suitable for use in agriculture.

The weight ratio of compound 1-1 1 to component 2 is preferably from 1 :20 to 20:1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. It may be preferred for the weight ratio to be 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 1-1 1 to component 3 is in the range from 1 :20 to 20:1 . It may be preferred for the weight ratio to be 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 1-1 1 to component 3 is in the range from 1 :20 to 20:1 , and in particular in the range from 1 :10 to 10:1 . It may be preferred for the weight ratio to be in the range from 1 :3 to 3:1 , in particular from 1 :2 to 2:1.

According to one embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , fluxapyroxad and pyraclostrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 2:1 and component 2 :

component 3 from 1 :1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 2:1 :2 or 2:1 :2 to 2:1 :1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to another embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , fluxapyroxad and pyraclostrobin for controlling cereal pathogens, where the components are present in the weight ratios mentioned above.

According to a specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. This mixture is furthermore suitable for controlling wheat pathogens selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella

herpotrichoides.

According to a further specific embodiment, this ternary mixture is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. This mixture is furthermore suitable for controlling barley pathogens selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, this ternary mixture is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, this ternary mixture is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae- maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, this ternary mixture is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, this ternary mixture is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis.

According to a further specific embodiment, this mixture is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate. According to a further specific embodiment, this ternary mixture is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, this ternary mixture is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using the ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea,

Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , fluxapyroxad and fenpropimorph, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :3 to 1 :6 and component 2 :

component 3 from 1 :3 to 1 :6. It may be preferred for the components to be present in a weight ratio of from 1 :1 :3 to 1 :1 :6, where according to one aspect the isomers 1-1 1 a, I- 1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts. According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , fluxapyroxad and fenpropimorph for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above. According to a further specific embodiment, this mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

According to yet a further specific embodiment, this mixture is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

fluxapyroxad and fenpropimorph is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular selected from the group consisting of Podosphaera leucotricha and Venturia inaequalis.

Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of

Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and fluxapyroxad, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 2:2:1. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 : 1 to 2:1 and component 2 : component 3 from 1 :1 to 2:1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and fluxapyroxad for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 2:1 and component 2 : component 3 from 1 :1 to 2:1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis,

Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluxapyroxad is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and bixafen, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 2:2:1 . In particular, the weight ratios of the three components are component 1 :

component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 2:1 and component 2 : component 3 from 1 :1 to 2:1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts. According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and bixafen for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 2:1 and component 2 :

component 3 from 1 :1 to 2:1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and bixafen is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis,

Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and

Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and bixafen is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and penflufen, where two of the

components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 2:2:1. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 : 1 to 2:1 and component 2 : component 3 from 1 :1 to 2:1 , where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and penflufen is used for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and penflufen is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides. According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and

Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and penflufen is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solaniPotato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and pyraclostrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 1 :1 :2. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 1 :2 and component 2 : component 3 from 1 :1 to 1 :2. Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling cereal pathogens, where the components are used in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and pyraclostrobin is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and pyraclostrobin is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis. According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and pyraclostrobin is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and dimoxystrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of from 1 :1 :1 to 1 :1 :2. In particular, the weight ratios of the three components are component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 :1 to 1 :2 and component 2 : component 3 from 1 :1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and dimoxystrobin is used for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminisAccording to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae. According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and dimoxystrobin is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and picoxystrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 : 1 to 1 :2 and component 2 : component 3 from 1 :1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and picoxystrobin for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and picoxystrobin is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternate and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and fluoxastrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 : 1 to 1 :2 and component 2 : component 3 from 1 :1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and fluoxastrobin for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis,

Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis.According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (=

Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and fluoxastrobin is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola.

According to yet a further embodiment, the present invention relates to the ternary mixture of compound 1-1 1 , prothioconazole and orysastrobin, where two of the components are present in a weight ratio of from 20:1 to 1 :20, more specifically from 5:1 to 1 :5, in particular from 2:1 to 1 :2, where according to one aspect the isomers I- 1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . It may be preferred for the components to be present in a weight ratio of component 1 : component 2 from 1 :1 to 2:1 ; component 1 : component 3 from 1 : 1 to 1 :2 and component 2 : component 3 from 1 :1 to 1 :2, where according to one aspect the isomers 1-1 1 a, 1-1 1 b, 1-1 1 c and 1-1 1 d are in each case present individually or as a mixture, in particular as a mixture of the two diastereomers (which are in each case pairs of enantiomers) in ratios of from 5:1 to 1 :5 or from 4:1 to 1 :4, in particular from 2:1 to 1 :2, specifically 1 :1 . Surprisingly, this mixture shows synergistic effects and the components are employed in particular in synergistically effective amounts.

According to a specific embodiment, the present invention relates to the use of the ternary mixture of compound 1-1 1 , prothioconazole and orysastrobin is used for controlling cereal pathogens, where the components are employed in the weight ratios mentioned above.

According to a further specific embodiment, this ternary mixture is used for controlling wheat pathogens, where the wheat pathogens are selected in particular from the group consisting of Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis,

Puccinia recondita, Puccinia striiformis and Blumeria graminis (mildew). According to a further specific embodiment, the wheat pathogens are selected from the group consisting of Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. According to a further specific embodiment, the mixture of compound 1-1 1 , prothioconazole and orysastrobin is used for controlling barley pathogens, in particular selected from the group consisting of Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. According to a further specific embodiment, the barley pathogens are selected from the group consisting of Ramularia collo-cygni and Pseudocercosporella herpotrichoides.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling soybean pathogens, in particular selected from the group consisting of Phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soybeans, this mixture may also be used effectively for controlling FDC (Foliar Disease Complex), for example against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling corn pathogens, in particular selected from the group consisting of Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling sugar beet pathogens, in particular selected from the group consisting of Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling peanut pathogens, in particular selected from the group consisting of Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling oilseed rape pathogens, in particular selected from the group consisting of Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling rice pathogens, in particular selected from the group consisting of Rhizoctonia solani and Pyricularia oryzae

According to a further specific embodiment, the mixture of compound 1-1 1 ,

prothioconazole and orysastrobin is used for controlling pathogens in special crops such as, for example, in lawn, potatoes, tomatoes, cucurbits, grapevines, apples, ornamental plants and bananas. Lawn pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sclerotinia homeocarpon and Rhizoctonia solani. Potato and tomato pathogens which can be controlled in accordance with the present invention are in particular selected from the group consisting of Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen which can be controlled using this ternary mixture according to the invention is in particular Sphaerotheca fuliginea. A grapevine pathogen which can be controlled using this ternary mixture according to the invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen which can be controlled using this ternary mixture according to the invention is in particular

Podosphaera leucotricha and Venturia inaequalis. Ornamental plant pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Sphaerotheca fuliginea, Diplocarpon spp.,

Alternaria spp. and Sclerotinia spp. Banana pathogens which can be controlled using this ternary mixture according to the invention are in particular selected from the group consisting of Mycosphaerella fijiensis and Mycosphaerella musicola. Synthesis examples:

The compounds of the formula I can be synthesized according to the documents cited above (see WO 2010/029001 , WO 2010/029002, WO 2010/029000, WO 2010/029003, WO 2010/031721 , WO 2010/031847, WO 2010/031848, WO 2010/031842 and WO 2010/040718 (PCT/EP2009/061370, PCT/EP2009/061372, PCT/EP2009/061368, PCT/EP2009/061373, PCT/EP2009/061693, PCT/EP2009/062129,

PCT/EP2009/062130, PCT/EP2009/062122 and PCT/EP2009/062909)).

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

Micro test

Preparation of active compound

The active compounds were formulated separately or jointly as a stock solution having a concentration of 10 000 ppm in DMSO. The active compound orysastrobin was used as a commercial formulation and, with respect to the active compound, diluted with water.

The determined values (measured parameters) for the percentage of infection on the leaves were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds and were thus converted into efficacy % of the untreated control. An efficacy of 0 means the same degree of infection as in the untreated control; an efficacy of 100 means 0% infection. The expected efficacies for active compound combinations were determined using the Colby formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp. 20 - 22, 1967) and compared to the observed efficacies.

The efficacy (E) is calculated as follows using Abbot's formula:

E = (1 - α/β) · 100

a corresponds to the fungal infection of the treated plants in % and

β corresponds to the fungal infection of the untreated (control) plants in % At an efficacy of 0 the degree of infection of the treated plants corresponds to that of the untreated control plants; at an efficacy of 100 the treated plants are not infected. The expected efficacies for active compound combinations were determined using the Colby formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1 5, pp. 20 - 22, 1967) and compared to the observed efficacies. Colby's formula:

E = x + y - x-y/100

E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active

compound A at the concentration a

y efficacy, expressed in % of the untreated control, when using the active

compound B at the concentration b Use example No. M1 - Activity against the gray mold pathogen Botrytis cinerea in the microtiter test (Botrci)

The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active compound concentration with water. An aqueous malt-based spore suspension of Botrytis cinerea was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds.

Use example No. M2 - Activity against the rice blast pathogen Pyricularia oryzae in the microtiter test (Pyrior)

The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active compound concentration with water. An aqueous malt-based spore suspension of Pyricularia oryzae was then added. The plates were placed in a water vapor- saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (=100%) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. Use example No. M3 - Activity against the Septoria leaf blotch pathogen Septoria tritici in the microtiter test (Septtr)

The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active compound concentration with water. An aqueous malt-based spore suspension of Septoria tritici was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. The determined values for the relative growth in percent were initially averaged and then converted into efficacies in % of the active compound-free control variant. An efficacy of 0 is the same growth as in the active compound-free control variant, an efficacy of 100 is 0% growth.

The expected efficacies for active compound combinations were determined using the Colby formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1 5, pp. 20 - 22, 1967) and compared to the observed efficacies.

Results:

Botrci

Active compound / Concentration Mixture Observed Calculated Synergism

Active compound (ppm) activity activity

mixture according to

Colby (%)

compound B 16 - 29

4 - 20

compound C 1 - 62

compound D 4 - 27

compound F 1 - 36

compound G 16 - 27

4 - 15

compound H 1 - 33

compound J 16 - 38

4 - 21

metconazole 0.063 - 37

tebuconazole 0.25 - 37

0.063 - 13

hexaconazole 0.063 - 31

0.016 - 12

fenbuconazole 0.063 - 23

0.016 - 1 1

prothioconazole 0.063 - 15

triflumizole 4 - 27 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

1 - 0

diniconazole 0.25 - 13

0.063 6

bromuconazole 0.063 - 27

epoxiconazole 0.25 - 55

0.063 29

difenoconazole 0.25 - 23

0.063 15

compound B 4 63 : 1 67 49 18 metconazole 0.063

compound B 16 63 : 1 84 55 29 tebuconazole 0.25

compound B 4 63 : 1 : 1 84 55 29 metconazole 0.063

tebuconazole 0.063

250 : 4 :

compound B 4 1 83 54 29 metconazole 0.063

hexaconazole 0.016

compound C 1 63 : 1 90 66 24 fenbuconazole 0.016

16 : 1 :

compound C 1 16 97 68 29 prothioconazole 0.063

triflumizole 1

compound C 1 63 : 4 : 1 94 71 23 prothioconazole 0.063

fenbuconazole 0.016

compound D 4 63 : 1 83 55 28 metconazole 0.063

compound D 4 63 : 1 : 1 85 55 30 metconazole 0.063

diniconazole 0.063

compound F 1 16 : 1 99 53 46 bromuconazole 0.063

compound F 1 4 : 1 89 60 29 tebuconazole 0.25 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound F 1 1 : 4 85 53 32 triflumizole 4

compound F 1 16 : 1 100 51 49 fenbuconazole 0.063

compound G 16 63 : 1 91 67 24 epoxiconazole 0.25

compound G 4 63 : 1 65 46 19 metconazole 0.063

compound G 16 63 : 1 70 44 26 difenoconazole 0.25

compound G 4 63 : 1 : 1 86 62 24 epoxiconazole 0.063

metconazole 0.063

compound G 16 63 : 1 : 1 93 71 22 epoxiconazole 0.25

diniconazole 0.25

compound G 4 63 : 1 : 1 80 53 27 metconazole 0.063

tebuconazole 0.063

compound H 1 16 : 1 82 58 24 metconazole 0.063

compound H 1 16 : 1 : 1 89 64 25 metconazole 0.063

tebuconazole 0.063

compound H 1 63 : 4 : 1 83 63 20 metconazole 0.063

hexaconazole 0.016

compound H 1 16 : 1 : 1 87 51 36 tebuconazole 0.063

difenoconazole 0.063

compound J 16 63 : 1 100 72 28 epoxiconazole 0.25

compound J 16 63 : 1 100 46 54 diniconazole 0.25 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound J 4 63 : 1 61 32 29 tebuconazole 0.063

compound J 16 250 : 1 100 57 43 hexaconazole 0.063

compound J 16 63 : 1 100 52 48 difenoconazole 0.25

compound J 4 4 : 1 47 21 26 triflumizole 1

compound J 16 250 : 1 100 52 48 fenbuconazole 0.063

Pyrior

Active compound / Concentration Mixture Observed Calculated Synergism

Active compound (ppm) activity activity

mixture according to

Colby (%)

compound A 0.063 - 13

compound B 16 - 30

compound C 0.25 - 16

compound G 16 - 9

compound H 1 - 53

compound J 16 - 52

4 - 2

epoxiconazole 0.25 - 18

0.063 - 0

metconazole 0.25 - 17

0.063 - 1

tebuconazole 0.25 - 12

0.063 - 0

prothioconazole 0.25 - 14

0.063 - 3

0.016 - 0

triflumizole 4 - 14

1 - 4

0.25 - 3

diniconazole 0.25 - 34

0.063 - 1

bromuconazole 0.016 - 1 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

hexaconazole 0.063 - 8

0.016 0

flutriafol 1 - 1 1

0.25 1

fenbuconazole 0.063 - 13

0.016 0

difenoconazole 0.25 - 1 1

triticonazole 0.25 - 8

compound A 0.063 1 : 4 96 41 55 epoxiconazole 0.25

metconazole 0.25

compound A 0.063 1 : 4 92 38 54 metconazole 0.25

tebuconazole 0.25

compound B 16 63 : 1 85 52 33 epoxiconazole 0.25

metconazole 0.25

compound B 16 63 : 1 89 50 39 metconazole 0.25

tebuconazole 0.25

16 : 1 :

compound C 0.25 16 37 18 19 prothioconazole 0.016

triflumizole 0.25

compound G 16 63 : 1 60 40 20 diniconazole 0.25

compound G 16 63 : 1 : 1 94 50 44 metconazole 0.25

diniconazole 0.25

compound G 16 63 : 1 81 34 47 metconazole 0.25

tebuconazole 0.25

compound H 1 16 : 1 79 53 26 epoxiconazole 0.063

Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%) Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound H 1 16 : 1 91 53 38 metconazole 0.063

compound H 1 16 : 1 76 53 23 diniconazole 0.063

compound H 1 16 : 1 76 52 24 tebuconazole 0.063

compound H 1 16 : 1 76 54 22 prothioconazole 0.063

compound H 1 63 : 4 : 1 76 54 22 epoxiconazole 0.063

bromuconazole 0.016

compound H 1 16: 1 : 1 94 53 41 epoxiconazole 0.063

metconazole 0.063

compound H 1 16: 1 : 1 94 55 39 metconazole 0.063

diniconazole 0.063

compound H 1 16: 1 : 1 96 52 44 metconazole 0.063

tebuconazole 0.063

compound H 1 63 : 4 : 1 89 53 36 metconazole 0.063

hexaconazole 0.016

compound H 1 63 : 4 : 1 78 53 25 tebuconazole 0.063

hexaconazole 0.016

compound H 1 16: 1 : 1 94 53 41 tebuconazole 0.063

prothioconazole 0.063

16: 1 :

compound H 1 16 89 56 33 prothioconazole 0.063

triflumizole 1

compound H 1 16: 1 :4 98 54 44 prothioconazole 0.063

flutriafol 0.25

compound H 1 63 : 4 : 1 81 54 27 prothioconazole 0.063

fenbuconazole 0.016 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound J 4 63 : 1 96 3 93 epoxiconazole 0.063

compound J 4 250 : 1 89 4 85 bromuconazole 0.016

compound J 16 63 : 1 98 60 38 metconazole 0.25

compound J 16 63 : 1 99 69 30 diniconazole 0.25

compound J 16 63 : 1 99 58 41 tebuconazole 0.25

compound J 16 250 : 1 99 56 43 hexaconazole 0.063

compound J 16 63 : 1 99 58 41 difenoconazole 0.25

compound J 16 63 : 1 99 59 40 prothioconazole 0.25

compound J 16 4 : 1 95 59 36 triflumizole 4

compound J 16 250 : 1 98 59 39 fenbuconazole 0.063

Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound J 16 63 : 1 94 56 38 triticonazole 0.25

250 : 4 :

compound J 16 1 88 62 26 tebuconazole 0.25

hexaconazole 0.063

compound J 16 63 : 1 : 1 96 65 31 tebuconazole 0.25

prothioconazole 0.25

63 : 1 :

compound J 16 16 98 65 33 prothioconazole 0.25

triflumizole 4

compound J 16 63 : 1 : 4 97 64 33 prothioconazole 0.25 Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

flutriafol 1

250 : 4 :

compound J 16 1 98 65 33 prothioconazole 0.25

fenbuconazole 0.063

Septtr

Active compound / Concentration Mixture Observed Calculated Synergism

Active compound (ppm) activity activity

mixture according to

Colby (%)

compound A 0.004 - 14

compound B 1 - 45

0.25 - 1

compound D 1 - 21

0.25 - 13

compound E 0.016 - 4

compound F 0.25 - 17

5673764 4 - 16

compound H 0.25 - 34

compound J 4 - 2

epoxiconazole 0.063 - 46

0.016 - 0

0.004 - 1

prothioconazole 0.016 - 22

0.004 - 2

triflumizole 1 - 0

0.25 - 0

bromuconazole 0.016 - 10

0.004 - 8

diniconazole 0.063 - 18

0.016 - 8

0.004 - 0

tebuconazole 0.063 - 8

0.016 - 5

0.004 - 0

hexaconazole 0.016 - 34

0.004 - 12 0.001 - 6

difenoconazole 0.016 - 40

metconazole 0.063 - 48

0.016 9

flutriafol 0.063 - 10

fenbuconazole 0.016 - 39

0.004 1 1 triticonazole 0.063 13

Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

1773639 0.004 1 : 4 : 4 47 21 26 epoxiconazole 0.016

diniconazole 0.016

compound B 0.25 63 : 1 33 2 31 epoxiconazole 0.004

compound B 0.25 63 : 1 40 3 37 prothioconazole 0.004

compound B 1 4 : 1 68 45 23 triflumizole 0.25

250 : 4 :

compound B 1 1 72 50 22 epoxiconazole 0.016

bromuconazole 0.004

compound B 1 63 : 1 : 1 79 49 30 epoxiconazole 0.016

diniconazole 0.016

250 : 4 :

compound B 0.25 1 32 8 24 tebuconazole 0.004

hexaconazole 0.001

compound D 0.25 63 : 1 33 13 20 diniconazole 0.004

compound D 1 63 : 1 85 53 32 difenoconazole 0.016

compound D 1 63 : 1 : 1 74 29 45 metconazole 0.016

diniconazole 0.016

compound D 1 63 : 1 : 1 67 31 36 metconazole 0.016

tebuconazole 0.016 compound D 1 63 : 1 : 1 89 54 35 tebuconazole 0.016

difenoconazole 0.016

compound E 0.016 1 : 4 71 49 22 metconazole 0.063

compound F 0.25 16 : 1 75 25 50 bromuconazole 0.016

compound F 0.25 16 : 1 65 45 20 hexaconazole 0.016

compound F 0.25 1 : 4 84 17 67 triflumizole 1

compound G 4 63 : 1 51 31 20 diniconazole 0.063

250 : 4 :

compound G 4 1 81 60 21 epoxiconazole 0.063

bromuconazole 0.016

compound G 4 63 : 1 : 1 83 63 20 epoxiconazole 0.063

diniconazole 0.063

compound H 0.25 16 : 1 78 40 38 metconazole 0.016

compound H 0.25 63 : 1 64 42 22 hexaconazole 0.004

compound H 0.25 16 : 1 79 48 31 prothioconazole 0.016

compound H 0.25 16 : 1 : 1 72 43 29 metconazole 0.016

tebuconazole 0.016

Active compound / Concentration Mixture Observed Calculated Synergism Active compound (ppm) activity activity

mixture according to

Colby (%)

compound H 0.25 63 : 4 : 1 79 47 32 metconazole 0.016

hexaconazole 0.004

compound H 0.25 63 : 4 : 1 71 44 27 tebuconazole 0.016

hexaconazole 0.004

compound H 0.25 16 : 1 : 1 82 37 45 tebuconazole 0.016 prothioconazole 0.016

16 : 1 :

compound H 0.25 16 86 48 38 prothioconazole 0.016

triflumizole 0.25

compound H 0.25 16 : 1 : 4 95 53 42 prothioconazole 0.016

flutriafol 0.063

compound H 0.25 63 : 4 : 1 86 54 32 prothioconazole 0.016

fenbuconazole 0.004

compound J 4 63 : 1 93 47 46 epoxiconazole 0.063

compound J 4 250 : 1 95 13 82 bromuconazole 0.016

compound J 4 63 : 1 96 20 76 diniconazole 0.063

compound J 1 4 : 1 35 15 20 triflumizole 0.25

compound J 4 250 : 1 86 41 45 fenbuconazole 0.016

compound J 4 63 : 1 83 15 68 triticonazole 0.063

compound J 4 63 : 1 : 1 96 56 40 epoxiconazole 0.063

diniconazole 0.063

250 : 4 :

compound J 4 1 75 40 35 tebuconazole 0.063

hexaconazole 0.016

Greenhouse

Active compound preparation

The active compounds were prepared separately or jointly as a stock solution comprising 25 mg of active compound which was made up to 10 ml with a mixture of acetone and/or DMSO and the emulsifier Wettol EM 31 (wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent/emulsifier of 99:1 . The mixture was then made up to 100 ml with water. This stock solution was diluted with the solvent/emulsifier/water mixture described to give the active compound concentration stated below. Alternatively, the active compounds were used as commercial finished formulations and diluted with water to the stated active compound concentration. G1. Activity against gray mold on bell pepper leaves caused by Botrytis cinerea, protective application (Botrci P1 )

Seedlings of green bell peppers were grown in pots. Once 2 - 3 leaves were well- developed, they were sprayed to runoff point with an aqueous suspension having the active compound concentration stated below. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea in a 2% biomalt solution. The test plants were then placed in a dark climatized chamber of 22 to 24°C and high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %.

G2. Protective activity against Septoria tritici on wheat (Septtr P1 )

Leaves of potted wheat seedlings were sprayed to runoff point with an aqueous suspension having the active compound concentration stated below. The plants were air- dried. The next day, the plants were inoculated with an aqueous spore suspension of Septoria tritici . The test plants were then immediately transferred into a humid chamber of 18-22°C and an atmospheric humidity of almost 100%. After 4 days, the plants were transferred into a chamber of 18-22°C and an atmospheric humidity of about 70%. After 4 weeks, the extent of the infection on the leaves was determined visually in %.

G3. Protective activity against Puccinia recondita on wheat (brown rust of wheat) (Puccrt P1 )

The first two developed leaves of potted wheat seedlings were sprayed to runoff point with an aqueous suspension having the active compound concentration stated below. The next day, the treated plants were inoculated with a spore suspension of brown rust of wheat (Puccinia recondita). The plants were then placed in a dark chamber at high atmospheric humidity (95 to 99%) at 20 to 24°C for 24 hours. The test plants were then placed in a greenhouse chamber at 20-24°C and a relative humidity between 65 and 70% for 6 days. The extent of the infection on the leaves was determined visually in %.

G4. Protective activity against soybean rust on soybeans caused by Phakopsora pachyrhizi (Phakpa P1 )

Leaves of potted soybean seedlings were sprayed to runoff point with an aqueous suspension having the active compound concentration stated below. The plants were air- dried. The next day, the treated plants were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were placed in a humid chamber with a high atmospheric humidity of about 95 and 20 to 24°C for 24 hours. The test plants were cultivated in a greenhouse chamber at 23-27°C and a relative atmospheric humidity of 60 and 80% for 14 days. The extent of the rust fungus

development on the leaves was determined visually in %. The determined values for relative growth in percent on the infected leaves were initially averaged and then converted into efficacies in % of the untreated control. An efficacy of 0 means the same degree of infection as in the untreated control; an efficacy of 100 means 0% infection. The expected efficacies for active compound combinations were determined using the Colby formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1 5, pp. 20-22, 1967) and compared to the observed efficacies.

Results:

Botrci P1

Figure imgf000144_0001

Septtr P1

Figure imgf000144_0002
Puccrt PI Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%)

Mixture according

to Colby

(%)

untreated 80%

control infection

compound D 4 - 6

0.25 1

pyraclostrobin 0.25 - 13

prothioconazole 4 - 13

bixafen 1 - 13

compound D 0.25 1 : 1 44 14 30 pyraclostrobin 0.25

compound D 4 1 : 1 47 18 29 prothioconazole 4

compound D 4 4 : 4 : 1 56 28 28 prothioconazole 4

bixafen 1

Phakpa P1

Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%)

Mixture according

to Colby

(%)

untreated 42%

control infection

compound D 0.063 - 2

fluxapyroxad 0.016 - 0

pyraclostrobin 0.063 - 0

bixafen 0.016 - 60

compound D 0.063 4 : 1 56 2 54 fluxapyroxad 0.016

compound D 0.063 1 : 1 40 2 38 pyraclostrobin 0.063

compound D 0.063 4 : 1 90 62 28 bixafen 0.016

compound D 0.063 4 : 1 : 4 91 2 89 fluxapyroxad 0.016

pyraclostrobin 0.063 Micro test

The active compounds were formulated separately or jointly as a stock solution having a concentration of 10 000 ppm in DMSO. M4. Activity against Rhynchosporium secalis in the microtiter test (Rhynse)

The stock solutions were mixed according to the stated ratios, pipetted onto a microtiter plate and diluted with water to the stated concentration. An aqueous malt-based spore suspension of Rhynchosporium secalis was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation.

M5. Activity against Pyrenophora teres of barley in the microtiter test (Pyrnte)

The stock solutions were mixed according to the stated ratios, pipetted onto a microtiter plate and diluted with water to the stated concentration. An aqueous malt-based spore suspension of Pyronophora feres was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation.

M6. Activity against Septoria glycines in the microtiter test (Septgl)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. An aqueous malt-based spore suspension of Septoria glycines was then added. The plates were placed in a water vapor- saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation.

The percentages obtained were converted into efficacies. The expected efficacies for active compound combinations were determined using the Colby formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide Combinations", Weeds, 15, pp. 20-22, 1967) and compared to the observed efficacies.

Results:Rhynse

Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%) Mixture according

to Colby

(%)

compound D 4 - 19

0.063 5

fenpropimorph 1 - 74

0.25 50

chlorothalonil 0.25 - 41

fluxapyroxad 0.063 - 49 Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%)

Mixture according

to Colby

(%)

compound D 4 4 : 1 100 79 21 fenpropimorph 1

compound D 1 4 : 1 71 47 24 chlorothalonil 0.25

compound D 0.063 1 : 1 : 4 93 76 17 fluxapyroxad 0.063

fenpropimorph 0.25

Pyrnte

Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%)

Mixture according

to Colby

(%)

compound D 0.25 - 1

fluxapyroxad 0.016 - 50

pyraclostrobin 0.016 - 39

compound D 0.25 16 : 1 : 1 87 70 17 fluxapyroxad 0.016

pyraclostrobin 0.016

Septgl

Active Concentration Mixture Observed Calculated Synergism compound / (ppm) activity activity (%)

Mixture according

to Colby

(%)

compound D 1 - 10

chlorothalonil 0.25 - 22

fluxapyroxad 0.063 - 33

pyraclostrobin 0.063 - 68

compound D 1 4 : 1 54 30 24 chlorothalonil 0.25

compound D 1 16 : 1 : 1 100 81 19 fluxapyroxad 0.063

pyraclostrobin 0.063

Structures Compound A

Compound B

Compound C

Compound D

Compound E

Compound F

Compound G

Compound H

Compound J

Figure imgf000148_0001

Claims

Claims
1. A fungicidal mixture comprising, as active components,
1 ) a triazolyl compound selected from the compounds of the formula I
Figure imgf000149_0001
in which the variables have the following meanings:
X is H or D; where D is as defined below:
D - is S-R10, where
R10 is hydrogen, Ci-Cs-alkyI, Ci-Ce-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C(=0)R11, C(=S)R11, S02R12 or CN; where
R11 is Ci-C8-alkyl, Ci-C8-haloalkyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy or NA3A4, where A3 and A4 are as defined below:
A3,A4 independently of one another are hydrogen, Ci-C8-alkyl, Ci-C8-haloalkyl, C3-C8-cycloalkyl, phenyl;
R12 is Ci-C8-alkyl, phenyl-Ci-C8-alkyl or phenyl, where the phenyl groups are in each case unsubstituted or substituted by one, two or three groups independently selected from the group consisting of halogen and Ci-C4-alkyl;
- is a group Dl
Figure imgf000149_0002
where the variables are as defined above; - is a group DM
Figure imgf000150_0001
where # is the point of attachment to the azolyl ring and Q, R13 and R14 are as defined below:
Q is O or S;
R13, R14 independently of one another are Ci-Cs-alkyl, Ci-Cs- haloalkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, C3-C8-cycloalkyl, phenyl, phenyl-Ci-C4-alkyl, phenoxy, phenyl-Ci-C4- alkoxy or NR15R16, where R15 is H or d-Cs-alkyl and R16 is Ci-C8- alkyl, phenyl-Ci-C4-alkyl or phenyl;
or
- is a group SM, where M is as defined below:
M is an alkali metal cation, an equivalent of an alkaline earth metal cation, an equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
E2
E1— N-E3 (E)
in which
E1 and E2 independently of one another are hydrogen or Ci-Cs-alkyl;
E3 and E4 independently of one another are hydrogen, Ci-Cs-alkyl, benzyl or phenyl; where the phenyl groups are in each case unsubsti- tuted or substituted by one, two or three groups independently of one another selected from the group consisting of halogen and Ci-C4- alkyl;
Y is O or a single bond to R1;
Z is a saturated hydrocarbon chain which has two to five carbon atoms and which may contain one, two or three substituents Rz, where Rz is as defined below:
Rz is halogen, Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-Cs-alkenyl, C2-Cs-halo- alkenyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, C2-C8- alkenyloxy, C2-C8-haloalkenyloxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl,
Cs-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cyclo- alkenyloxy, Ci-C6-alkylene, oxy-C2-C4-alkylene, phenoxy, phenyl; where Rz is in each case unsubstituted or contains one, two or three independently selected groups L; is phenyl which is unsubstituted or contains one, two, three, four or five dependently selected substituents L, where L is as defined below:
L is halogen, C-i-Cs-alkyl, C-i-Cs-haloalkyl, C2-C8-alkenyl, C2-Cs-halo- alkenyl, C4-Cio-alkadienyl, C4-Cio-haloalkadienyl, d-Cs-alkoxy, Ci- Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, C2-C8-alkenyloxy, C2-Cs-halo- alkenyloxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl,
C3-C8-halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cycloalkenyloxy, Ci- C6-alkylene, the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:
RL is halogen, hydroxy, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocyclo- alkyl, Cs-Cs-cycloalkenyl, Cs-Cs-cycloalkoxy, Cs-Cs-halocycloalkoxy,
Ci-C6-alkylene, oxy-C2-C4-alkylene, oxy-Ci-C3-alkyleneoxy, Ci-Cs- alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkoxycarbonyl, amino, Ci-Ce-alkylamino, di-Ci-Cs-alkylamino; is hydrogen, halogen , Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-C1 haloalkenyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl; is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-halo- alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3-C10- cycloalkenyl, C3-Cio-halocycloalkenyl, tri-Ci-Cio-alkylsilyl; is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-halo- alkenyl, C3-Cio-cycloalkyl;
R2, R3 and R4 are, unless indicated otherwise, independently of one another unsubstituted or substituted by one, two, three, four or five L, as defined above; and agriculturally acceptable salts thereof; and
2) a fungicidal compound II which is selected from the following compounds: A) strobilurins:
azoxystrobin, dimoxystrobin, coumoxystrobin, coumethoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2- (6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)phenyl)-2-methoxyimino- N-methylacetamide, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-
3- methoxyacrylate, methyl 3-methoxy-2-(2-(N-(4-methoxyphenyl)- cyclopropanecarboximidoylsulfanylmethyl)phenyl)acrylate, 2-(2-(3-(2,6-dichloro- phenyl)-1 -methylallylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methyl- acetamide;
B) carboxamides:
carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, car- boxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kira- laxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-
4- methylthiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethylindan-4- yl)nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide, N-(2-(1 ,3-dimethylbutyl)phenyl)-1 ,3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide (penflufen), N-(2-(1 ,3,3- trimethylbutyl)phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;
carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;
benzamides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3-ethyl- 3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide;
- other carboxamides: carpropamid, diclocymet, mandipropamid, oxytetracy- clin, silthiofam, N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide;
C) azoles:
triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difeno- conazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquin- conazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, met- conazole, myclobutanil, oxpoconazole, padobutrazole, penconazole, propicona- zole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4-chlorophenyl)-2-([1 ,2,4]triazol-1 - yl)cycloheptanol;
- imidazoles: cyazofamid, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
others: ethaboxam, etridiazole, hymexazole, 2-(4-chlorophenyl)-N-[4-(3,4- dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;
D) nitrogenous heterocyclyl compounds
pyridines: fluazinam, pyrifenox, 3-[5-(4-chlorophenyl)-2,3- dimethylisoxazolidin-3-yl]pyridine, 3-[5-(4-methylphenyl)-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-chloropyridin-2-yl)ethyl)-2,4- dichloronicotinamide, N-((5-bromo-3-chloro-pyridin-2-yl)methyl)-2,4- dichloronicotinamide;
- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, me- panipyrim, nitrapyrin, nuarimol, pyrimethanil;
piperazines: triforine;
pyrroles: fludioxonil, fenpiclonil;
morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph;
piperidines: fenpropidin;
dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;
nonaromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, S-allyl 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3- dihydropyrazole-1 -thiocarboxylate;
others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzo- quat-methylsulfate, fenoxanil, folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propylchromen- 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]pyrimidin-7-ylamine;
E) carbamates and dithiocarbamates
thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulfocarb, metiram, propineb, thiram, zineb, ziram;
carbamates: diethofencarb, benthiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, valiphenal, 4-fluorophenyl N-(1 -(1 -(4- cyanophenyl)ethanesulfonyl)but-2-yl)carbamate;
F) other fungicides
- guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate);
antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
nitrophenyl derivatives: binapacryl, dicloran, dinobuton, dinocap, nitrothal isopropyl, tecnazene;
organometallic compounds: fentin salts, such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;
organophosphorus compounds: edifenphos, fosetyl, fosetyl aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide,
quintozene, thiophanate methyl, tolylfluanid, N-(4-chloro-2-nitrophenyl)-N-ethyl-4- methylbenzenesulfonamide;
inorganic active compounds: phosphorous acid and its salts, Bordeaux mix- ture, copper salts, such as, for example, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, pyriofenone, mildiomycin, oxine-copper, prohexadione-calcium, spi- roxamine, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3- difluorophenyl)methyl)-2-phenylacetamide, N'-(4-(4-chloro-3- trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine, N'-(4- (4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N- methylformamidine, N'-(2-methyl-5-trifluoromethyl-4-(3- trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine, N'-(5- difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N- methylformamidine, methyl N-(1 ,2,3,4-tetrahydronaphthalen-1 -yl)-2-{1 -[2-(5- methyl-3-trifluoromethylpyrazol-1 -yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, methyl (R)-N-(1 ,2,3,4-tetrahydronaphthalen-1 -yl)-2-{1 -[2-(5-methyl-3- trifluoromethylpyrazol-1 -yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, 6-tert- butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate, 6-tert-butyl-8-fluoro-2,3- dimethylquinolin-4-yl methoxyacetate, N-methyl-2-{1 -[2-(5-methyl-3-trifluoro- methyl-1 H-pyrazol-1 -yl)acetyl]piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydro- naphthalen-1 -yl]-4-thiazolecarboxamide;
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 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, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapac-ethyl and uniconazole;
H) herbicides
acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
amino acid analogs: bilanafos, glyphosate, glufosinate, sulfosate;
aryloxyphenoxypropionat.es: clodinafop, cyhalofop-butyl, fenoxaprop, fluazi- fop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-p-tefuryl;
- bipyridyls: diquat, paraquat;
carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedi- pham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedi- pham, prosulfocarb, pyributicarb, thiobencarb, triallate;
cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, seth- oxydim, tepraloxydim, tralkoxydim;
dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodia- mine, trifluralin;
diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesa- fen, lactofen, oxyfluorfen;
hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil;
imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imaza- quin, 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, norflurazone, pyridate; pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, flu- roxypyr, picloram, picolinafen, thiazopyr;
sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, fluce- tosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfu- ron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfu- ron, 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, hexazi- none, metamitron, 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, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsu- lam;
others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzo- quat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenza- nid, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methylarsenic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, 4-hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3- carbonyl]bicyclo[3.2.1]oct-3-en-2-one, ethyl (3-[2-chloro-4-fluoro-5-(3-methyl-2,6- dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)phenoxy]pyridin-2- yloxy)acetate, methyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate, 6- chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-ol, 4-amino-3-chloro-6-(4- chlorophenyl)-5-fluoropyridine-2-carboxylic acid, methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate and methyl 4-amino-3- chloro-6-(4-chloro-3-dimethylamino-2-fluorophenyl)pyridine-2-carboxylate;
I) insecticides
organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlor- pyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, me- thamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, o- xydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, pho- sphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulpro- phos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbo- furan, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pi- rimicarb, propoxur, thiodicarb, triazamate;
pyrethroids: allethrin, bifenthrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta- cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resme- thrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,
inhibitors of insect growth: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflu- muron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazin; b) ecdysone antagonists: halofenozide, me- thoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methopre- ne, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spiro- tetramate;
- nicotine receptor agonists/antagonists: clothianidin, dinotefuran, imidaclo- prid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -(2-chlorothiazol-5- ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
GABA antagonists: endosulfan, ethiprol, fipronil, vaniliprol, pyrafluprol, pyri- prol, 5-amino-1 -(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1 H-pyrazole-3- thiocarboxamide;
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; decouplers: chlorfenapyr;
- inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
insect molting inhibitors: cryomazine;
mixed function oxidase inhibitors: piperonyl butoxide;
sodium channel blockers: indoxacarb, metaflumizone;
- others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamid, chlorantraniliprol, cyazypyr (HGW86); cyeno- pyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyriflu- quinazon and [(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 cyclopropanecarboxylate; in a synergistically effective amount.
The fungicidal mixture according to claim 1 which comprises, as component 1 ), a compound of the formula I in which Y = a single bond to R1.
The fungicidal mixture according to claim 2 in which in formula I Z is furthermore, a saturated hydrocarbon chain which has three to five carbon atoms and is un- substituted or contains one, two or three substituents Rz, where Rz is as defined in claim 1 .
The fungicidal mixture according to any of claims 1 to 3 where in formula I of component 1 ) Z is a saturated hydrocarbon chain which has three or four carbon atoms and is unsubstituted or contains one, two or three substituents Rz, where Rz is as defined in claim 1 .
The fungicidal mixture according to any of claims 1 to 4 where in formula I of component 1 ) R1 is phenyl which contains one or two independently selected substituents L, as defined in claim 1 .
The fungicidal mixture according to any of claims 1 to 5 where in formula I of component 1 ) X is hydrogen.
The fungicidal mixture according to any of claims 1 to 6 where in formula I of component 1 ) X is D and D is -SH, S-CN, S-d-Ce-alkyl, S-C2-C6-alkenyl or SM where M is as defined below: an alkali metal cation, an equivalent of an alkaline earth metal cation, an equivalent of a copper or an ammonium cation of the formula (E) in which Z1 and Z2 independently are hydrogen or Ci-C4-alkyl and Z3 and Z4 independently are hydrogen, Ci-C4-alkyl or phenyl; where the phenyl group is unsubstituted or substituted by one, two or three groups independently selected halogen and Ci-C4-alkyl.
The fungicidal mixture according to any of claims 1 to 9 where in formula I of component 1 ) R2, R3 and R4 are hydrogen.
9. The fungicidal mixture according to any of claims 1 to 10 wherein component 1 ) is selected from among the following compounds:
-1 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2-fluorophenyl and R2, R3 and R4 are hydrogen;
-2 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2-chlorophenyl and R2, R3 and R4 are hydrogen;
-3 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2,4-dichlorophenyl and R2,
R3 and R4 are hydrogen;
-4 formula I in which X = H, Y = O, Z = (CH2)4, R1 = 2,4-difluorophenyl and R2,
R3 and R4 are hydrogen;
-5 formula I in which X = SH, Y = O, Z = (CH2)4, R1 = 2-fluorophenyl and R2,
R3 and R4 are hydrogen;
-6 formula I in which X = SH, Y = O, Z = (CH2)4, R1 = 2,4-difluorophenyl and
R2, R3 and R4 are hydrogen;
-7 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R1
= 2,4-difluorophenyl and R2, R3 and R4 are hydrogen;
-8 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 2-chloro-4-fluorophenyl and R2, R3 and R4 are hydrogen;
-9 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 2,4-dichlorophenyl and R2, R3 and R4 are hydrogen;
-10 formula I in which X = H, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 4-chloro-2-fluorophenyl and R2, R3 and R4 are hydrogen;
-1 1 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 2,4-dichlorophenyl and R2, R3 and R4 are hydrogen;
-12 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 4-chloro-2-fluorophenyl and R2, R3 and R4 are hydrogen;
-13 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 2-chloro-4-fluorophenyl and R2, R3 and R4 are hydrogen; and -14 formula I in which X = SH, Y = a single bond to R1, Z = CH2CH(CH3)CH2, R
= 2,4-difluorophenyl and R2, R3 and R4 are hydrogen. The fungicidal mixture according to any of claims 1 to 12 wherein component 2) is selected from the active substances:
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]pyrimidin-7-ylamine
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-1 H-pyrazole-4- carboxamide
II-26 sedaxane
II-27 isopyrazam
II-28 fluopyram
and
II-29 penflufen.
The fungicidal mixture according to any of claims 1 to 10 comprising an additional component 3) selected from the compounds II mentioned for component 2), where component 2) and 3) are different compounds.
The fungicidal mixture according to any of claims 1 to 1 1 comprising one of the components 1 ) and one of the components 2) in a weight ratio of from 100:1 to 1 :100.
13. An agrochemical composition comprising a solvent and/or a solid carrier and a fungicidal mixture according to any of claims 1 to 12.
14. Seed comprising a fungicidal mixture according to any of claims 1 to 12.
15. A method for controlling phytopathogenic fungi wherein the fungi or the materials, plants, the soil or seed to be protected from fungal attack are treated with an ef- fective amount of a fungicidal mixture according to any of claims 1 to 12.
PCT/EP2011/053519 2010-03-10 2011-03-09 Fungicidal mixtures comprising triazole derivatives WO2011110583A2 (en)

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EP10156311.2 2010-03-12
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