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WO2010146029A2 - Mélanges fongicides - Google Patents

Mélanges fongicides Download PDF

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Publication number
WO2010146029A2
WO2010146029A2 PCT/EP2010/058339 EP2010058339W WO2010146029A2 WO 2010146029 A2 WO2010146029 A2 WO 2010146029A2 EP 2010058339 W EP2010058339 W EP 2010058339W WO 2010146029 A2 WO2010146029 A2 WO 2010146029A2
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WO
WIPO (PCT)
Prior art keywords
methyl
phenyl
alkyl
compounds
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/EP2010/058339
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German (de)
English (en)
Other versions
WO2010146029A3 (fr
Inventor
Jochen Dietz
Egon Haden
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
Marianna Vrettou-Schultes
Silke Stolz
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BASF SE
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BASF SE
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Publication of WO2010146029A2 publication Critical patent/WO2010146029A2/fr
Publication of WO2010146029A3 publication Critical patent/WO2010146029A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention relates to fungicidal compositions comprising as active components
  • B is phenyl which is unsubstituted or substituted by one, two, three or four identical or different substituents L, where L is
  • L is halogen, cyano, nitro, cyanato (OCN), C -C 8 -alkyl, C 8 -HaIo- genalkyl, phenyl-Ci-C ⁇ -alkyloxy, C2-C8 alkenyl, C2-C8 haloalkenyl , C2-C8 alkynyl, C2-C8 haloalkynyl, C4-Cio-alkadienyl, C4-Cio-alkadienyl halogen, Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy, d- Cs-alkylsulfonyloxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C2-C 8 - alkynyloxy, C 2 -C 8 haloalkynyloxy, C 3 -C 8 cycloalkyl,
  • n 0, 1 or 2;
  • a 1 is hydrogen, hydroxy, Ci-C 8 alkyl-Al, Ci-C8-haloalkyl, amino, Ci-C 8 - alkylamino or di-Ci-C 8 alkylamino
  • a 2 is one of the groups mentioned at A 1 or C 2 -C 8 -alkenyl, C 2 -C 8 -
  • Halocycloalkyl C3-C8 cycloalkoxy or C3-C8-halo cycloalkoxy;
  • a 3 are independently hydrogen, Ci-C 8 alkyl, Ci-C 8 -HaIo- genalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl , C 2 -C 8 -
  • R L is halogen, cyano, nitro, Ci-C8 -alkyl, C 8 haloalkyl, C 8 - alkoxy, Ci-C8-haloalkoxy, C3-C8 cycloalkyl, C3-C 8 -Halogencyclo - alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkoxy, C3-C 8 -Halogencyclo- alkoxy, Ci-C8-alkylcarbonyl, Ci-C8-alkylcarbonyloxy, Ci-C 8 - alkoxycarbonyl, amino, Ci C 8 alkylamino, di-C 1 -C 8 alkylamino;
  • R 3 represents hydrogen, Ci-C 8 alkyl-Al, Ci-C8-haloalkyl, Ci-C 8 alkoxy,
  • R 4 is C 1 -C 8 -alkyl, phenyl-C 1 -C 8 -alkyl or phenyl, wherein the
  • Each phenyl group is unsubstituted or substituted with one, two or three groups independently selected from
  • R 1 independently of one another Ci-C 8 alkyl, Ci-C8-haloalkyl, d-Cs-alkoxy, Ci-Cs-alkoxy-d-Cs-alkoxy, Ci-C8-haloalkoxy, Ci-C 8 - alkoxy-Ci-Cs-alkyl, Ci -C 8 alkylthio -alkyl, C 2 -C 8 -alkenylthio, C 2 -C 8 -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C 3 -C 8 cycloalkylthio, phenyl, phenyl-Ci-C 4 - alkyl, phenoxy, phenylthio, phenyl-Ci-C4-alkoxy or NR 5 R 6, wherein
  • R 5 is H or C 1 -C 8 -alkyl and R 6 is C 1 -C 8 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl or R 5 and R 6 together represent an alkylene chain having four or five C atoms form or form a radical of the formula -CH 2 -CH 2 -O-CH 2 -CH 2 - or -CH 2 -CH 2 -NR 7 -CH 2 -CH 2 -, in which R 7 is hydrogen or C 1 -C 4 - Alkyl means; wherein the aromatic groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three groups selected from halogen and C 1 -C 4 -alkyl; or
  • M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
  • Z 1 and Z 2 are independently hydrogen or C 1 -C 8 -alkyl
  • Z 3 and Z 4 are independently hydrogen, C 1 -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
  • Azoxystrobin Dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy ) -5-fluoro-pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, Methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarbox-imidoylsulfanylmethyl) -phenyl) acrylate,
  • Carboxylic acid anilides benalaxyl, benalaxyl M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxylin, Penthiopyrad, Sedaxane, Tecloftalam, Thifluzamide, Tiadinil, 2-Amino
  • Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide; - Other carboxylic acid amides: carpropamide, diclocymet, mandipropamide,
  • - triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole,
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethylisoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 (5-Bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloronotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4 -dichlornicotinamid;
  • Pyrimidines Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil; - piperazines: triforins;
  • Dicarboximides fluorimide, iprodione, procymidone, vinclozolin; non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;
  • acibenzolar-S-methyl acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoate methyl sulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazide, pyroquilone, quinoxyfen , Triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1 - (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H- benzoimidazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a]
  • fentin salts such as fentin acetate, fentin chloride, fentin hydroxide
  • Sulfur-containing heterocyclyl compounds dithianone, isoprothiolanes;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4- methyl-benzenesulfonamide;
  • Inorganic active ingredients phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • Acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro;
  • Amino acid analogues bilanafos, glyphosate, glufosinate, sulfosate;
  • Aryloxyphenoxypropionates clodinafop, cyhalofopbutyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • Bipyridyls diquat, paraquat; Carbamates and thiocarbamates: asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallates;
  • - cyclohexanediones butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; - Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin;
  • Diphenyl ether acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • Hydroxybenzonitriles bromoxynil, dichlobenil, loxynil;
  • Imidazolinones imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
  • Phenoxyacetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;
  • Pyrazines Chloridazon, Flufenpyr-ethyl, Fluthiacet, Norflurazon, Pyridate; Pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • Sulfonylureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-prop
  • acetolactate synthase bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenzpropyl, pyribenzoxime, Pyriftalid, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyroxasulfone, Pyroxsulam;
  • Organo (thio) phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophos, methidathion, methyl parathion , Mevinphos, monocrotophos,
  • Carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb,
  • Pyrethroids allethrin, betacyfluthrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II,
  • Insect growth inhibitors a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin,
  • Nicotine receptor agonists / antagonists clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1- (2-chlorothiazol-5-ylmethyl) -2-nitrimino-3,5-dimethyl- [1, 3,5] triazinane;
  • GABA antagonists endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1- (2,6-dichloro-4-methylphenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide; Macrocyclic lactones: abamectin, emamectin, milbemectin, lepimectin,
  • METI II and III substances Acequinocyl, Fluacyprim, Hydramethylnon; - decoupler: chlorfenapyr;
  • Inhibitors of oxidative phosphorylation cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • Inhibitors of the sloughing of insects Cryomazine;
  • Inhibitors of mixed function oxidases piperonyl butoxide; Sodium channel blocker: indoxacarb, metaflumizone;
  • component 2 is defined as follows:
  • Biological fungicides, plant strengtheners Ampelomyces quis- qualis (. Eg the product AQ 10 ® from Intrachem Bio GmbH & Co. KG Germany,), Aspergillus flavus (. Eg the product AFLAGUARD ® from Syngenta, Switzerland), Aureobasidium pullulans (eg the product BOTECTOR ® from. bio-ferm GmbH, Germany), Bacillus pumilus (eg strain NRRL no. B-30087 ® in SONATA ®, and BALLAD Plus from. AgraQuest Inc., USA), Bacillus subtilis (eg master NRRL No. B-21661 in Rhapsody ®, SERENADE ® MAX and SERENADE ® ASO of Fa..
  • AgraQuest Inc., USA Bacillus subtilis var. Amyloliquefaciens FZB24 (eg the product TAEGRO ® from. Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (eg the product ASPIRE ® from. Ecogen Inc., USA), Candida saitoana (eg the products BIOCURE ® (mixed with lysozyme) and BIOCOAT ® Micro Flo Company. BotriZen Ltd., Company, USA (BASF SE) and Arysta) chitosan (eg ARMOR ZEN Fa New Zealand), Clonostachys rosea f. catenulata, also called
  • Gliocladium catenulatum eg strain J1446. PresTop ® from Verdera, Finland
  • Coniothyrium minitans eg the product Contans ® from Prophyta, Germany
  • Cryphonectria parasitica eg the product Endothia parasitica the company CNICM, France
  • Cryptococcus albidus eg the product YIELD PLUS ® from. Anchor bio- Technologies, South Africa
  • Fusarium oxysporum eg the products biofox ® from Siapa, Italy, and FUSACLEAN ® from. Natural Plant Protection, France
  • Metschnikowia fructicola eg the product Shemer ®, Fa..
  • Microdochium dimerum eg the product ANTI BOT ® from Agrauxine, France
  • Phlebiopsis gigantea eg the product ROTSOP ® from. Verdera, Finland
  • Pseudozyma flocculosa eg the product SPORODEX ® Plant Products Co. Ltd. Fa., Canada
  • Pythium oligandrum DV74 eg the product POLYVERSUM ® from.
  • REGALIA from Marrone Biol nnovations, USA
  • Talaromyces flavus V117b eg the product protus ® from. Prophyta, Germany
  • Trichoderma asperellum SKT-1 eg, the product
  • harzianum TH 35 eg the product ROOT PRO ® from MyControl Ltd., Israel
  • T. harzianum T-39 for example, the products TRICHODEX ® and TRICHODERMA 2000 ® from. MyControl Ltd., Israel and Makhteshim Ltd., Israel
  • T. harzianum and T. viride eg the product TRICHOPEL the company Agrimm Technologies Ltd, New Zealand
  • T. harzianum and T. viride ICC012 ICC080 eg the product retrier ® WP Fa. Isagro Ricerca, Italy
  • T. polysporum and T. harzianum eg product Binab ® from. Binab Bio-innovation AB, Sweden
  • T. virens GL 21 eg Pro domestic product SOILGARD ® from Certis LLC, USA
  • T. viride eg the products TRIECO ® from Ecosense Labs. (India) Pvt. Ltd., India and BIO-CURE ® F from. T. Stanes & Co. Ltd., India
  • T. viride TV1 eg the product T.
  • viride TV1 company Agribiotec srl, Italy Ulocladium oudemansii HRU3 (eg the product BOTRY- ZEN ® of Botry-Zen Ltd Company, New Zealand); wherein components 1) and 2) are present in a synergistically effective amount.
  • the invention relates to the use of the fungicidal mixtures for controlling phytopathogenic fungi and agents or compositions containing them. Furthermore, the invention also relates to seed containing the fungicidal mixtures. Furthermore, the invention also relates to methods for Control of phytopathogenic fungi, characterized in that treating the fungi, or to be protected against fungal attack materials, plants, the soil or seeds with an effective amount of a fungicidal mixture according to the invention. Furthermore, the invention also relates to processes for the preparation of the mixtures according to the invention.
  • the invention relates to fungicidal mixtures comprising 1) Azolylmethyloxirane of the general formula I as described above, and 2) a compound II, wherein the compound II of the component 2 is selected from the compounds of groups A to I as described above,
  • the invention relates to fungicidal mixtures comprising
  • the mixtures comprising at least one compound of the formula I (component 1) and at least one further active compound II (component 2 and optional component 3) are the mixtures according to the invention.
  • the mixtures according to the invention are preferably binary mixtures, particularly preferably ternary mixtures.
  • Azolylmethyloxiranes of component 1 their preparation and their use in crop protection are known from WO 2009/077471 (PCT / EP2008 / 067483), in which certain mixtures of Azolylmethyloxirane of component 1 are mentioned with other active ingredients.
  • Azolylmethyloxiranes of the general formula I are the compounds I according to the invention.
  • component 2 and 3 The active ingredients mentioned above as component 2 and 3, their preparation and their action against harmful fungi are known (cf .: http://www.alanwood.net/pesticides/); they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also (See, Can. J.
  • the present invention mixtures were the object, which show an improved action against harmful fungi, especially for certain indications with reduced total amount of applied drugs.
  • the present invention therefore also relates, in particular, to fungicidal compositions which comprise at least one compound of the general formula I and at least one further fungicidal active ingredient (component 2 and optional component 3), eg. B. one or more, for example 1 or 2 active ingredients of the aforementioned groups A to I and optionally one or more agriculturally suitable carriers. It has also been found that, with simultaneous simultaneous or separate application of the compound I and one or more compounds II or when using the compound I and the compound (s) II harmful fungi can be controlled better than with the individual compounds (synergistic mixtures).
  • Common application in the context of this application means that at least one compound I and the at least one other active ingredient II at the same time at the site of action (ie the fungi to be controlled and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces) in an amount sufficient for effective control of fungal growth available.
  • the site of action ie the fungi to be controlled and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces
  • the time sequence of the application of the active ingredients is of minor importance.
  • these are binary mixtures, i. H.
  • Compositions according to the invention comprising a compound I and another active ingredient II (component 2), e.g. contain an active ingredient from groups A) to I).
  • the weight ratio of compound I to further active ingredient II depends on the properties of the respective active ingredients, usually in the range from 1: 100 to 100: 1, frequently in the range from 1:50 to 50: 1, preferably in the range from 1 : 20 to 20: 1, more preferably in the range of 1:10 to 10: 1, in particular in the range of 1: 3 to 3: 1. It may also be preferred that the weight ratio is in the range of 1: 2 to 2: 1.
  • compositions according to the invention comprising an active ingredient I and a further active ingredient (component 2) and a second further active ingredient (component 3), for. B. contain two different agents from groups A) to I).
  • the weight ratio of compound I to the first further active ingredient (component 2) depends on the properties of the respective active ingredients, preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1 and in particular in the range from 1:20 to 20: 1. It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1.
  • the weight ratio of compound I to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1:20 to 20: 1 , It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1.
  • the weight ratio of further active ingredient (component 2) to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1. It may be preferred that the weight ratio is in the range from 1:10 to 10: 1, preferably from 1: 3 to 3: 1, in particular from 1: 2 to 2: 1.
  • composition according to the invention can be mixed individually or already mixed or packaged as parts according to the kit of parts and reused.
  • kits one or more, also all, contain components that can be used to prepare an agrochemical composition of the invention.
  • these kits may contain one or more fungicidal component (s) and / or an adjuvant component and / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • fungicidal component s
  • an adjuvant component / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • One or more components may be combined or pre-formulated.
  • the components may be combined together and packaged in a single container such as a vessel, bottle, can, bag, sack or canister.
  • two or more components of a kit may be packaged separately, ie, not pre-formulated or mixed.
  • Kits may contain one or more separate containers such as containers, bottles, cans, bags, sacks or canisters, each container containing a separate component of the agrochemical composition.
  • the components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the "kit of parts" and reused. In both forms, one component can be used separately or together with the other components or as part of a kit of parts according to the invention for the preparation of the mixture according to the invention.
  • the user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane.
  • the agrochemical composition with water and / or buffer is brought to the desired application concentration, optionally further adjuvants are added, and thus the ready-spray mixture or the agrochemical composition according to the invention is obtained.
  • 50 to 500 liters of ready-spray mixture per hectare of agricultural land preferably 100 to 400 liters.
  • the user may include individual components such as B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).
  • individual components such as B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).
  • the user can mix both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups A) to I), in the spray tank and optionally add further auxiliaries (tank mix).
  • the user can use both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups A) to I), together (for example as tank mix) or in succession.
  • the compounds of the formula I can be present in the "thiol" form of the formula Ia or in the "thiono" form of the formula Ib:
  • R wherein R has the meaning defined above;
  • the compounds I are able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them. This also applies to most of the precursors for compounds I described herein, of which the salts and adducts are also subject of the present invention.
  • inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms).
  • Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl which are a or two phosphoric acid radicals), wherein the alkyl or aryl radicals may carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
  • metal ions in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth
  • Main group in particular aluminum, tin and lead, as well as the first to eighth subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others into consideration.
  • Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • the compounds I contain chiral centers and are generally obtained in the form of racemates or as mixtures of diastereomers of erythro and threo forms.
  • the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers.
  • antimicrobial agents can be used both the uniform diastereomers or enantiomers as well as their resulting in the synthesis of mixtures. The same applies to the fungicides.
  • the invention therefore relates both to mixtures in which compound I are the pure enantiomers or diastereomers as well as mixtures thereof.
  • the scope of the present invention includes the mixtures of the (R) and (S) isomers and the racemates of the compounds I which have chiral centers.
  • Suitable compounds I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds of the formula I according to the invention can be prepared in various ways in analogy to known processes of the prior art (see, for example, US Pat in the cited prior art and crop protection news Bayer 57/2004, 2, pages 145-162), or as described in PCT / EP2008 / 067483.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkylamino saturated straight-chain or branched hydrocarbon radicals having from 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3
  • Methylpentyl 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
  • Haloalkyl alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above; in particular C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1, 1 , 1-
  • Alkenyl and the alkenyl moieties in compounded groups such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position.
  • alkenyloxy unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position.
  • alkenyl groups are, for example, C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -Methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-methyl
  • Haloalkenyl alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkadienyl unsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;
  • Alkynyl as well as the alkynyl moieties in compounded groups straight or branched chain hydrocarbon groups of 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-he
  • Haloalkynyl alkynyl, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkyl and the cycloalkyl moieties in assembled groups mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, in particular 3 to 6 carbon ring members, for example Cs-C ⁇ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • Halogencycloalkyl cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexene 4- yl and the like;
  • Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkoxy for an oxygen-bonded alkyl group as defined above, preferably with 1 to 8, more preferably 2 to 6 carbon atoms. Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; as well as e.g.
  • Pentoxy 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 , 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • Haloalkoxy alkoxy as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • Examples are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy, 2,
  • Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6) -
  • Alkylene more preferably (C 2 -C 4) -alkylene, furthermore it may be preferred (Ci-C 3 ) - Use alkylene groups.
  • preferred alkylene radicals are CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CH 2 ) 2 CH 2 , CH 2 (CH 2 ) 3 CH 2 and CH 2 (CH 2 ) 4 CH 2 ;
  • a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S, where the respective heterocycle via a carbon atom or via a nitrogen atom, if contained, may be attached. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • heterocyclyl three- or four-membered saturated heterocycle (hereinafter also heterocyclyl) containing one or two heteroatoms from the group O, N and S as ring members; A five- or six-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as
  • Ring members e.g. monocyclic saturated or partially unsaturated heterocycles containing, in addition to carbon ring members, one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3
  • hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2, -3, -4, -5, -6, or -7-yl, 2,3,4,7- Tetrahydro [1H] oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
  • the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • the heterocycle means in particular: -5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present 5-ring heteroaryl groups which may contain, in addition to carbon atoms, one to four nitrogen atoms or one, two or three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg furyl,
  • -6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered ring heteroaryl groups which, in addition to carbon atoms, have one to four or .
  • One, two or three nitrogen atoms may contain as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-
  • B is unsubstituted phenyl.
  • B represents phenyl which contains one, two, three or four independently selected substituents L.
  • the phenyl ring is monosubstituted with a substituent L, wherein L is according to a particular embodiment of this embodiment in the ortho position to the point of attachment of the phenyl ring with the oxirane ring.
  • B represents phenyl containing two or three independently selected substituents L.
  • B is a phenyl ring which contains a substituent L in the ortho position and also has a further independently selected substituent L.
  • the phenyl ring is 2,3-disubstituted.
  • the phenyl ring is 2,4-disubstituted.
  • the phenyl ring is 2,5-disubstituted.
  • the phenyl ring is 2,6-disubstituted.
  • B is a phenyl ring which contains a substituent L in the ortho position and also contains two further independently selected substituents L.
  • the phenyl ring is 2,3,5-trisubstituted.
  • the phenyl ring is 2,3,4-tri- substituted.
  • the phenyl ring is 2,4,5-trisubstituted.
  • a 1 is hydrogen, hydroxy, Ci-C 4 -alkyl, Ci-C4-haloalkyl;
  • a 2 is one of the groups mentioned at A 1 or C 1 -C 4 -alkoxy, C 1 -C 4 -
  • Haloalkoxy C 3 -C 6 -cycloalkyl, Cs-C ⁇ -halocycloalkyl, C 3 -C ⁇ -cycloalkoxy or C 3 -C 6 -halocycloalkoxy;
  • a 3 , A 4 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl;
  • L Remaining definitions of L can in turn carry one, two, three or four identical or different groups RL:
  • R L is halogen, cyano, nitro, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 - alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, Cs-C ⁇ -halocycloalkyl, Amino, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino.
  • L is independently selected from halogen, NO2, amino -C 4 - alkyl, Ci-C 4 alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino, d-C 4 - Dialkylamino, thio and Ci-C 4 alkylthio.
  • L is independently selected from halogen, Ci-C 4 alkyl, -C 4 - haloalkyl, Ci-C4-alkoxy, Ci-C4 haloalkoxy, and Ci-C4-haloalkylthio.
  • L is independently selected from F, Cl, Br, CH 3, C 2 H 5, iC 3 H 7, tC 4 H 9, OCH 3, OC 2 H 5, CF 3, CCl 3, CHF 2 , CCIF 2 , OCF 3 , OCHF 2 and SCF 3 , in particular selected from F, Cl, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CF 3 , CHF 2 , OCF 3 , OCHF 2 and SCF 3 , According to one embodiment, L is independently selected from F, Cl, CH 3, OCH 3, CF 3, OCF 3 and OCHF. 2 It may be preferred that L is independently F or Cl.
  • the substituent B is phenyl which is substituted by one, two or three halogen atoms.
  • B is phenyl which is unsubstituted or substituted by one, two or three substituents independently selected from halogen, NO 2 , amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 4 haloalkyl, Ci-C 4 - haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, and Ci-C 4 alkylthio.
  • B is not ortho-methylphenyl.
  • D is a group SR, where R is hydrogen (compounds I-SH).
  • D is a group SR, where R is C 1 -C 4 -alkyl, in particular methyl or ethyl, preferably methyl.
  • R 3 is hydrogen.
  • R 3 is C 1 -C 4 -alkyl, in particular methyl or ethyl, preferably methyl.
  • R 3 is C 1 -C 4 -haloalkyl, in particular trifluoromethyl.
  • R 3 is C 1 -C 4 -alkoxy, in particular methoxy or ethoxy.
  • Phenylamino means.
  • R 3 is methylamine, dimethylamino, ethylamino, diethylamino or phenylamino.
  • D is a group SR, where R is CN.
  • D is a group SR, where R is SO 2 R 4 and R 4 is C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl, where the phenyl groups are each unsubstituted or are substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl.
  • D is a group SM, wherein M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E )
  • Z 1 and Z 2 are independently hydrogen or C 1 -C 4 -alkyl; and Z 3 and Z 4 are independently hydrogen, Ci-C 4 -AlkVl, benzyl or phenyl.
  • M represents Na, 1 ⁇ 2Cu, 3Fe, HN (CH 3 ) S, HN (C 2 H 5 ) S, N (CHs) 4 or H 2 N (C 3 HT) 2 , in particular Na, 1/2 Cu, HN (CHs) 3 or HN (C 2 Hs) 3 , especially Na, 1/2 Cu, HN (CHs) 3 or HN (C 2 Hs) 3 .
  • the invention relates to mixtures of the compounds of the formula I in which the variables have the following meanings: B is phenyl which is substituted in the ortho position by a further substituent L, where L is
  • L is fluorine, chlorine, bromine, Ci -C 8 -alkyl, C 8 alkoxy, C 3 -C 8 cycloalkyl, C 3 -C 8 -
  • a 2 is hydrogen, hydroxy, Ci-C 8 -alkyl, C 8 haloalkyl, amino, d-C8-alkylamino or di-Ci-C 8 alkylamino, Ci-C 8 alkoxy;
  • R3 is hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-
  • R 4 is C 1 -C 8 -alkyl, phenyl-C 1 -C 8 -alkyl or phenyl, wherein the
  • Each phenyl group is unsubstituted or substituted with one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
  • R 1 independently of one another Ci-C 8 alkyl, Ci-C8-haloalkyl, d-Cs-alkoxy, Ci-Cs-alkoxy-d-Cs-alkoxy, Ci-C8-haloalkoxy, Ci-C 8 - alkoxy-Ci-C 8 alkyl, C -C alkylthio 8 -alkyl, C 2 -C 8 -alkenylthio, C 2 -C 8 -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C 3 -C 8 cycloalkylthio , phenyl, phenyl-Ci-C 4 - alkyl, phenoxy, phenylthio, phenyl-Ci-C4-alkoxy or NR 5 R 6, wherein
  • R 5 is H or C 1 -C 8 -alkyl and R 6 is C 1 -C 8 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl or R 5 and R 6 together represent an alkylene chain having four or five C atoms form or form a radical of the formula -CH 2 -CH 2 -O-CH 2 -CH 2 - or -CH 2 -CH 2 -NR 7 -CH 2 -CH 2 -, in which R 7 is hydrogen or C 1 -C 4 - Alkyl means; wherein the aromatic groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three groups selected from halogen and C 1 -C 4 -alkyl; or
  • M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
  • Z 1 and Z 2 are independently hydrogen or C 1 -C 8 -alkyl
  • Z 3 and Z 4 are independently hydrogen, C 1 -C 6 -alkyl, benzyl or phenyl
  • the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl
  • the invention relates to mixtures of the compounds of the formula I in which the variables have the following meanings:
  • B is phenyl substituted in ortho position with another substituent L, wherein L is: L is fluoro, chloro, bromo, methyl;
  • R 4 is C 1 -C 8 alkyl
  • M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
  • Z 1 and Z 2 are independently hydrogen or Ci-Cs-alkyl
  • Z 3 and Z 4 are independently hydrogen, C 1 -C 6 -alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
  • D in the compounds of formula I is --SO 2 R 4 , wherein R 4 and B are as defined herein.
  • D is a group D1 (compounds 1-dimer), where B is independently defined as defined herein or preferably:
  • both B in the compounds l-dimer have the same meaning.
  • D is a group Dil, where # is the point of attachment to the triazolyl ring and Q, R 1 and R 2 are as defined herein or preferably defined:
  • B is phenyl which is substituted by a substituent L, where L is
  • L is halogen, C 1 -C 8 -alkyl, C 1 -C -haloalkyl.
  • the components 2 and 3 are preferably selected independently of one another as described in the following compositions:
  • a compound I (component 1) in particular a compound selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10, and as component 2 comprise an active ingredient from the group A) of strobilurins, wherein component 2 is in particular selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • these are binary mixtures which contain only the two components as active ingredients.
  • these mixtures comprise a further component (component 3) selected from the group B) of the carboxamides, in particular selected from bixafen,
  • Boscalid fluopyram, isopyrazam, penthiopyrad, sedaxanes, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide and penflufen.
  • compositions of a compound I with at least one active compound selected from the group B) (component 2 and / or 3) of the carboxamides and especially selected from bixafen, boscalid, isopyrazam,
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • compositions of a compound I with at least one active ingredient selected from group C) (component 2 and / or 3) of the azoles and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil .
  • the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, 1-8 , 1-9 and 1-10.
  • compositions of a compound I with at least one active ingredient selected from group D) (component 2 and / or 3) of the nitrogen-containing heterocyclyl compounds and especially selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, Fodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin,
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • compositions of a compound I with at least one active ingredient selected from the fungicides of group F) (component 2 and / or 3) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl aluminum, H3PO3 and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and N-methyl-2- ⁇ 1 - [(5-methyl-3-trifluoromethyl-1H -pyrazol-1-yl) -acetyl] -piperidin-4-yl ⁇ -N - [(1 R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide.
  • the compound I component 1 with at least one active ingredient selected from the fung
  • the compositions according to the invention comprise a compound I (component 1), and a component 2, wherein the component 2 is a G) growth regulator.
  • component 2 is selected from chlormequat (chlorequat chloride), mepiquat (mepiquat chloride), metconazole, paclobutrazole, prohexadione (prohexadione-calcium), trinexapac-ethyl and uniconazole.
  • the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, 1-8 , 1-9 and 1-10.
  • compositions according to the invention comprise a compound I (component 1), and a component 2, wherein the component 2 is an insecticide selected from group I).
  • these are binary mixtures comprising as active ingredients a component 1) and a component 2) which is selected from group I).
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from the group of organo (thio) phosphates, in particular selected from acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl parathion, monocrotophos, phorates, profenofos and terbufos.
  • organo (thio) phosphates in particular selected from acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl parathion, monocrotophos, phorates, profenofos and terbufos.
  • the compound is I
  • Component 1 each selected from the compounds 1-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, 1-9 and 1-10.
  • insecticide of component 2) is selected from the group of carbamates, in particular selected from aldicarb, carbaryl, carbofuran, carbosulfan, methomyl and thiodicarb.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from the group of pyrethroids, in particular selected from: bifenthrin, cyfluthrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, lambda-cyhalothrin and tefluthrin.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from the group of inhibitors of insect growth, in particular selected from lufenuron and spirotetramat.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from the group of nicotine receptor agonists / antagonists, in particular selected from: clothianidin, imidacloprid, thiamethoxam and thiacloprid.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from the group of GABA antagonists, in particular selected from: endosulfan and fipronil.
  • the compound I (component 1) is in each case selected from the compounds 1-1, I-2, I-
  • the insecticide of component 2) is selected from the group of macrocyclic lactones, in particular selected from: abamectin, emamectin, spinosad and spinetoram.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is hydramethylnone. According to a specific embodiment of the invention, the
  • Compound I in each case selected from the compounds 1-1, I-2, I-3, I-
  • the insecticide of component 2) is fenbutatin oxide.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • the insecticide of component 2) is selected from chlorfenapyr, cyazypyr (HGW86), cyflumetofen, flonicamid, flubendiamide, indoxacarb and metaflumizone.
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • these are ternary mixtures which, in addition to the components mentioned, comprise a component 3) which is selected from the above-mentioned active compounds II of group I).
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • these are ternary mixtures which, in addition to the two components mentioned, comprise a component 3) which is selected from the active compounds II of groups A) to G).
  • the compound I (component 1) is in each case selected from the compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8 , I-9 and 1-10.
  • Particularly preferred mixtures are the binary mixtures of Table B, wherein each line corresponds to one embodiment of the mixtures according to the invention.
  • Table B Binary mixtures comprising a component 1 selected from compounds of the formula I and a component 2 selected from the groups A to
  • the active compounds II as component 2) are the following:
  • the active compounds II as component 2) are the following:
  • the active compounds II as component 2) are the following: II-49 azoxystrobin
  • the active substance as component 2) is the following
  • composition II which are selected from the group of growth regulators G), in particular selected from the following compounds:
  • particularly preferred components 2 are compounds II, which are selected from group I), in particular selected from the following compounds: 11-1 a Acephat II-2a Chlorpyrifos ll-3a dimethoate ll-4a methamidophos ll-5a terbufos ll-6a aldicarb ll-7a carbofuran ll-8a bifenthrin ll-9a alpha-cypermethrin
  • particularly preferred components are 2
  • particularly preferred components 2 are compounds II which are selected from the active ingredients of group H).
  • the active compounds according to this embodiment are selected from the group of the following compounds of group H): 11-1 b glyphosate II-2b imazamox
  • Particularly preferred components 3 are compounds II which are selected from the group of the following compounds:
  • component 2 and component 3 are not the same.
  • Particularly preferred mixtures are the ternary mixtures of Table T, each line corresponding to one embodiment of the mixtures according to the invention.
  • Table T Ternary mixtures comprising a component 1 selected from compounds of the formula I, one component 2 selected from the groups A to and one component 3 selected from the groups A to I.
  • component 1 preference is given to mixtures which comprise a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of compounds 11-1 to II-29, Il 34, II-46 to 11-51, II-56 and II-57 (see above), and component 3 is a compound II selected from the compounds
  • component 2 and component 3 are not the same.
  • component II-55 prohexadione calcium of group G prohexadione calcium of group G
  • component 2 and component 3 are not the same.
  • preference is given to those mixtures comprising a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of the following compounds :
  • component 3 is a compound II selected from the group of the following compounds: II-30a fipronil II-32a clothianidin II-34a imidacloprid II-35a thiamethoxam
  • ternary mixtures which comprise a component 1, a component 2 and a component 3, particular preference being given to those mixtures in which component 2 is a compound II which is selected from the group of the following compounds : II-8 Kresoxim-methyl
  • 11-51 is penthiopyrad and component 3 is fipronil (Compound ll-30a).
  • the mixtures of compounds I and II are suitable as fungicides for controlling harmful fungi. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, which in particular originate from the classes of the Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytriomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. In addition, they are suitable for controlling fungi that attack, among other things, the wood or the roots of plants.
  • mixtures according to the invention and the compositions of the invention for combating a variety of pathogenic fungi on various crops such as cereals, eg. Wheat, rye, barley, triticale, oats or rice; Beets, z. Sugar or fodder beets; Kernel, stone and berry fruits, z. Apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; Legumes, z. Beans, lentils, peas, alfalfa or soybeans; Oil plants, e.g.
  • Rapeseed mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palm, peanuts or soya
  • Cucurbits z. Pumpkins, cucumbers or melons
  • Fiber plants z. Cotton, flax, hemp or jute
  • Citrus fruits z. Oranges, lemons, grapefruit or mandarins
  • Vegetables z. Spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or paprika
  • Energy and raw material plants eg.
  • Corn soy, wheat, rapeseed, sugarcane or oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (table and grapes); Hop; Grass, z. B. lawn; Sweet herb (Stevia rebaudania); Rubber plants; Ornamental and forest plants, z. As flowers, shrubs, deciduous and coniferous trees and on the propagation material, for. B. seeds, and the crop of these plants.
  • the mixtures or compositions of the invention for controlling a variety of fungal pathogens in crops, z.
  • Fruit, vine and ornamental plants and vegetables eg. Cucumbers,
  • Tomatoes Tomatoes, beans and pumpkins and on the propagation material, eg. B. seeds, and the crop of these plants used.
  • plant propagating materials includes all generative parts of the plant, e.g. As seeds, and vegetative plant parts, such as cuttings and tubers (eg., Potatoes), which can be used to propagate a plant. These include seeds, roots, fruits, tubers, onions, rhizomes, shoots and others
  • Plant parts including seedlings and young plants, which are transplanted after germination or emergence.
  • the young plants can be treated by a partial or complete treatment, eg. B. by immersion or pouring, are protected from harmful fungi.
  • Compositions are used to control a variety of fungal pathogens in cereal crops, e.g. Wheat, rye, barley or oats; Rice, corn, cotton and soy used.
  • crops also includes those plants which have been modified by breeding, mutagenesis or genetic engineering methods, including biotechnological agricultural products currently on the market or under development (see for example http://www.bio.org/speeches/pubs/ er / agri_products .asp).
  • Genetically engineered plants are plants whose genetic material has been altered in a way that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • Such genetic engineering also includes post-translational modifications of proteins, oligo- or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.
  • auxin herbicides such as auxin herbicides such.
  • B. Dicamba or 2,4-D bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors, acetolactate synthase (ALS) -I inhibitors such.
  • HPPD hydroxyphenylpyruvate dioxygenase
  • PDS phytoene desaturase
  • ALS acetolactate synthase
  • EPSPS Enolpyruvylshikimat-3-Phosphate synthase
  • GS glutamine synthetase
  • glufosinate lipid biosynthesis inhibitors such.
  • Acetyl-CoA carboxylase (ACCase) inhibitors or oxynil herbicides (eg, bromoxynil or loxynil).
  • crops were produced that are resistant to several herbicide classes by several genetic engineering measures, for example, resistant to glyphosate and glufosinate, or against glyphosate and a herbicide of another class such.
  • ALS inhibitors, HPPD inhibitors, auxin herbicides and ACCase inhibitors are e.g. As described in Pest Managers. Be.
  • Tribenuron Using genetic engineering methods, crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade names Roundup Ready ® (glyphosate-resistant, Monsanto, USA) Cultivance ® (imidazolinone -resistent, BASF SE, Germany) and Liberty link ® (glufosinate-resistant, Bayer CropScience, Germany) are available Sind.Weiterhin also includes plants using genetic engineering measures with one or more toxins, for. B. those from the bacterial strain Bacillus produce. Toxins produced by such genetically engineered plants include e.g.
  • Insecticidal proteins of Bacillus spp. In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B.
  • Wepsen, spider or scorpion toxins e.g. B. from streptomycetes; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, e.g.
  • RIPs Ribosome Inactivating Proteins
  • 3-hydroxy steroid oxidase ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blocker e.g. B. inhibitors of sodium or calcium channels
  • Juvenile hormone esterase e.g. B. inhibitors of sodium or calcium channels
  • Receptors for the diuretic hormone (helicokinin receptors) e.g. B. inhibitors of sodium or calcium channels
  • Receptors for the diuretic hormone (helicokinin receptors) helicokinin receptors
  • Stilbene synthase bibenzyl synthase, chitinases and glucanases.
  • These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073 discloses. The methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above.
  • YieldGard ® (Corn varieties that produce the toxin CrylAb), YieldGard ® Plus (corn varieties that produce the CrylAb and Cry3Bb1 toxins), Starlink ® (maize varieties that produce the Cry9c toxin), Herculex ® RW (maize varieties that contain the toxins Cry34Ab1, Cry35Ab1 and produce the enzyme phosphinothricin N-acetyltransferase [PAT]); NuCOTN ® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ® I (cotton cultivars producing the toxin CrylAc), Bollgard ® Il (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIPCOT ® (cotton varieties that produce a VIP toxin); NewLeaf ® (potato cultivars producing the Cry3A toxin); Bt-Xtra ®,
  • plants which produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as.
  • PR proteins pathogenesis-related proteins
  • resistance proteins eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum
  • T4 lysozyme z B. Potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein).
  • plants are included whose productivity has been improved by genetic engineering methods by z.
  • yield eg biomass, grain yield, starch, oil or protein content
  • tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.
  • plants are included whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z.
  • As oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids eg Nexera ® - rape, DOW Agro Sciences, Canada.
  • plants are included, which have been modified for the improved production of raw materials by means of genetic engineering methods by z.
  • compositions for controlling the following plant diseases Albugo spp. (White rust) on ornamental plants, vegetable crops (eg A. Candida) and sunflowers (eg BA tragopogonis); Alternaria spp. (Blackness, black spotiness) on vegetables, oilseed rape (for example BA brassicola or A. brassicae), sugar beet (for example BA tenuis), fruit, rice, soybeans and on potatoes (eg A. solani or A. alternata) and tomatoes (eg BA solani or A. alternata) and Alternaria spp. (Earwires) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg.
  • Botrytis cinerea Botryotinia fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including salad, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (cereal); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z. BC ulmi (elm dying, Dutch elm disease) on elms; Cercospora spp.
  • Velvet spot disease and cereals, e.g. B. C. herbarum (wheat spike) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (eg C. carbonum), cereals (eg C. sativus, anamorph: B. sorokiniana: brown spot) and rice (eg C. miyabeanus, anamorph: H. oryzae); Colletotrichum (Teleomorph: Glomerella) spp.
  • soybeans ; Drechslera (Syn. Helminthosporium, Teleomorph: Pyrenophora) spp. on corn, cereals such as barley (eg BD teres, nettles) and wheat (eg BD tritici- repentis: DTR leaf drought), rice and turf; Esca disease (grapevine dying, apoplexy) on grapevine caused by Formitiporia (Syn. Phellinus) punctata, F.
  • Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa
  • Epicoccum spp. (Earwires) on wheat
  • Erysiphe spp. Puldery mildew) on sugar beet (E.
  • betae vegetables
  • BE pisi vegetables
  • cucumber for example BE cichoracearum
  • cabbage plants such as rapeseed (for example, B. cruciferarum)
  • Eutypa lata Ertypa crab or extinction, Anamorph: Cytosporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental shrubs
  • Exserohilum Syn. Helminthosporium
  • spp. on maize (eg BE turcicum)
  • Fusarium Gibberella
  • spp. Wang, root and stalk rot
  • BM graminicola (Anamorph: Septoria tritici, Septoria leaf drought) on wheat or M. fijiensis (Black Sigatoka disease) on bananas; Peronospora spp. (Downy mildew) on cabbage (for example BP brassicae), oilseed rape (for example P. parasitica), bulbous plants (for example BP destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust)
  • soybeans Phialophora spp. z. On grapevines (eg BP tracheiphila and P. tetraspora) and soybeans (eg BP gregata: stalk disease); Phoma Hungary (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spots) on sugar beet; Phomopsis spp. on sunflowers, grapevine (eg BP viticola: black spot disease) and soybeans (eg stalk rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora spp.
  • BP capsici e.g. BP capsici
  • soybeans eg BP megasperma, Syn. P. sojae
  • potatoes and tomatoes eg. BP infestans: herbaceous and brown rot
  • deciduous trees eg BP ramorum: sudden oak mortality
  • Plasmodiophora brassicae cabbage hernia
  • Plasmopara spp. z. BP viticola (vine peronospora, downy mildew) on vines and P. halstedii on sunflowers
  • Puccinia spp. Puccinia spp. (Rust disease) on various plants, eg. BP triticina (wheat brown rust), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (black rust) or P. recondita (rye brown rust) on cereals, such as. Wheat, barley or rye, P. kuehnii to sugar cane and z.
  • BP triticina wheat brown rust
  • P. striiformis yellow rust
  • P. hordei dwarf rust
  • P. graminis black rust
  • P. recondita rye brown rust
  • BP asparagi on asparagus eg BP asparagi
  • Pyrenophora anamorph: Drechslera
  • tritici- repentis leaf drought
  • wheat or P. teres net stains
  • Pyricularia spp. E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and cereals
  • Pythium spp. (Turnip disease) on turf, rice, corn, wheat, cotton, oilseed rape, sunflower, sugar beets, vegetables and other plants (eg BP ultimum or P. aphanidermatum)
  • Ramularia spp. Z. BR collocygni (speckle disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets
  • Rhizoctonia spp. on cotton, rice, potatoes,
  • Erysiphe necator prowdery mildew, anamorphic: Oidium tuckeri
  • Setospaeria spp. (Leaf spot) on corn (e.g., S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (Dust fires) on maize, (eg S. reiliana: flaming spirit), millet and sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits;
  • Spongospora subterranea (powder scab) on potatoes and the viral diseases transmitted thereby; Stagonospora spp. on cereals, z. BS nodorum (leaf and tan, Teleomorph: Leptosphaeria [Syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato cancer); Taphrina spp., Z. BT deformans (curling disease) on peach and T. pruni (pocket disease) on plums; Thielaviopsis spp. (Black root rot) to tobacco, pome fruit, Vegetable crops, soybeans and cotton, e.g.
  • BT basicola (Syn: Chalara elegans); Tilletia spp. (Stone or Stinkbrand) of cereals, such.
  • BT tritici (Syn. T. caries, Weizensteinbrand) and T. controversa (Zwergsteinbrand) on wheat; Typhula incarnata (snow) on barley or wheat; Urocystis spp., E.g. BU occulta (stalk brandy) on rye; Uromyces spp. (Rust) on vegetables, such as beans (for example, appendiculatus appendix, Syn. U. phaseoli) and sugar beet (for example, Betae); Ustilago spp.
  • beans for example, appendiculatus appendix, Syn. U. phaseoli
  • sugar beet for example, Betae
  • Cultivated crops such as. B. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • the mixtures or compositions according to the invention are also suitable for controlling harmful fungi in the storage protection (also of crops) and in the protection of materials and buildings.
  • material and building protection covers the protection of technical and non-living materials such. As adhesives, glues, wood, paper and cardboard, textiles, leather, color dispersions, plastics, coolants, fibers and tissues, against the infestation and destruction by unwanted microorganisms such as fungi and bacteria.
  • 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.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds of the formula I, and also those of the formula II, can be present in various crystal modifications whose biological activity may be different. Their mixtures are included in the scope of the present invention.
  • the mixtures or compositions according to the invention are suitable for increasing plant health.
  • the invention relates to a method for enhancing plant health by treating the plants, the plant propagating material and / or the place where the plants are to grow or grow with an effective amount of the compounds I or the compositions according to the invention.
  • plant health includes those conditions of a plant and / or its crop which are determined by various indicators individually or in combination with each other, such as yield (eg, increased biomass and / or increased content of utilizable ingredients), plant vitality (eg increased
  • Plant growth and / or greener leaves Plant growth and / or greener leaves), quality (eg. increased content or composition of certain ingredients) and tolerance to biotic and / or abiotic stress.
  • These plant health status indicators referred to herein may be independent or mutually exclusive.
  • the mixtures according to the invention are used as such or in the form of a
  • the application can be both before and after the infection of plants, plant propagating materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the mixture according to the invention.
  • the application can be both before and after the infection of plants, plant
  • Propagating materials eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.
  • Plant propagating materials may be used prophylactically together with or already before sowing or together with or even before transplanting with the mixtures according to the invention as such or with a composition of them (composition containing at least one compound I and at least one compound II, preferably one or two compounds II).
  • the invention relates to agrochemical compositions containing a solvent or solid carrier and the mixture according to the invention and their use for controlling harmful fungi.
  • agent is often used in this context to mean the term “composition”, in particular "agrochemical composition”, and “formulation”.
  • An agrochemical composition contains a fungicidally effective amount of the mixture according to the invention.
  • the expression "effective amount” means an amount of the agrochemical composition or mixture according to the invention which is sufficient for controlling harmful fungi on crop plants or in the protection of materials and buildings and does not lead to considerable damage to the treated crop plants vary widely and are influenced by numerous factors, such as the harmful fungus to be controlled, the particular crop or material being treated, climatic conditions and compounds.
  • the compounds I and the one or more compounds II can be applied simultaneously, jointly or separately or successively, the
  • Sequence with separate application in general has no effect on the control success.
  • the method of controlling harmful fungi is by the separate or combined application of the compound I and the compound (s) II or the mixtures of the compound I and the compound (s) II by spraying or dusting the seeds, the plants or the soil or after sowing the plants or before or after emergence of the plants.
  • the compounds I and II may be present in a common composition or in separate compositions.
  • the type and preparation of the particular composition corresponds to the type and preparation as generally described for compositions herein.
  • the compounds I and the compounds II and their N-oxides and salts or mixtures thereof can be converted into the types customary for agrochemical compositions, eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • agrochemical compositions eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the type of composition depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compounds of the mixtures according to the invention.
  • composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which may be either soluble or dispersible in water or gels for the treatment of plant propagating materials such as seeds (GF).
  • composition types eg EC, SC, OD, FS, WG, SG, WP, SP, SS, WS, GF
  • composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.
  • agrochemical compositions are prepared in a known manner (see, for example, US 3,060,084, EP-A 707,445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill, New York, 1963, 8-57 and et seq., WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (John Wiley & Sons, New York, 1961), Hance et al .: Weed Control Handbook (8th Ed., Blackwell Scientific Publications, Oxford, 1989) and Mollet, H. and Grubemann, A. : Formulation technology (Wiley VCH Verlag, Weinheim, 2001).
  • the agrochemical compositions can furthermore also contain auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.
  • auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment).
  • Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, gycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters and strongly polar solvents, eg amines such as N-methylpyrrolidone , considering.
  • solvent mixtures and mixtures of the abovementioned solvents and water can also be used.
  • Solid carriers are mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphthalene (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® types, BASF, Germany), and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesul
  • aromatic sulfonic acids eg. B. of lignin (Borresper
  • thickeners ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion
  • thickeners are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco, U.S.A.), Rhodopol ® 23 (Rhodia, France) or Veegum ® (RT Vanderbilt, USA) or attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added to stabilize the composition.
  • bactericides are those based on diclorophene and
  • Benzyl alcohol Proxel ®. Fa. ICI or Acticide ® RS from Thor Chemie and Kathon ® MK from. Rohm & Haas
  • isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide ® MBS from Thor Chemie).
  • Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
  • defoamers are silicone emulsions (such as, for example, Silikon® SRE, Wacker,
  • Rhodorsil ® Rhodia, France
  • long chain alcohols fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1, Pigment blue 15: 4,
  • adhesives examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose ethers (Tylose ®, Shin-Etsu, Japan).
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or
  • Powders, dispersants and dusts can be prepared by mixing or jointly grinding the compounds I and the further active compounds II with at least one solid carrier.
  • Granules, for. As coated, impregnated and homogeneous granules can be prepared by binding the active ingredients to at least one solid carrier.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, tree bark, wood and nut shell meal, cellulose powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, tree bark, wood and
  • compositions for dilution in water i) Water-soluble concentrates (SL, LS) 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a composition with 10 wt .-% active ingredient content. ii) Dispersible Concentrates (DC)
  • Emulsions (EW, EO, ES)
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added by means of an emulsifying machine (eg Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the composition has an active ingredient content of 25 wt .-%. v) suspensions (SC, OD, FS)
  • Spray tower fluidized bed
  • water-dispersible or water-soluble granules Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the composition has an active ingredient content of 50% by weight.
  • WP Water-dispersible and water-soluble powders (WP, SP, SS, WS)
  • compositions of the mixtures according to the invention generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I and II or mixtures thereof.
  • the compounds I and II are preferably used in a purity of 90% to 100%, preferably 95% to 100% (NMR spectrum).
  • For the treatment of plant propagation materials in particular seed, usually water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels ( GF).
  • LS water-soluble concentrates
  • FS suspensions
  • dusts DS
  • WS, SS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gels GF
  • compositions to be used for the stain The application can be done before or during sowing.
  • the treatment of plant propagation material in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, pelleting, dipping or impregnating the plant propagation material, wherein the treatment preferably takes place by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented.
  • suspensions are preferably used for seed treatment.
  • compositions contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water.
  • the compounds I and II or their mixtures can be used as such or in the form of their compositions, for. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, coating, dipping or pouring.
  • the composition types depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds or active substance mixtures according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be successfully used in the ultra-low-volume (ULV) process, whereby it is possible to apply compositions containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.001 and 2.0 kg of active ingredient per ha, preferably between 0.005 and 2 kg per ha, more preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha.
  • the application rate of active ingredient or active ingredient mixture depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • the active substances or active substance mixtures or the compositions containing them may contain oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides and / or pesticides, if necessary, also be added immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • adjuvants in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S 240® ; Alcohol alkoxylates, eg. B.
  • HPLC analyzes were performed using an Alltech Alltima C18 Rocket column, with PDA detection at 254 nm, on a Shimadzu Prominence HPLC system unless otherwise specified. At a flow rate of 2.5 mL per minute, the following schedule was used:
  • the reaction mixture was added with saturated ammonium chloride solution (30 ml) and then extracted with ethyl acetate (50 ml). The organic phase was washed with saturated sodium chloride solution (40 ml_ three times), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 3: 2 hexane / ethyl acetate), recrystallized with hexane / methylene chloride and purified by column chromatography (silica gel, 3: 2 hexane / ethyl acetate). The target compound (2.1 g, 38%) was obtained as a white solid.
  • the reaction mixture was added with methanol (10 mL) and saturated ammonium chloride solution (30 mL) and then extracted with ethyl acetate (50 mL). The organic phase was washed with saturated sodium chloride solution (three times 40 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 4: 1 methylene chloride / ethyl acetate). The objective compound (155 mg, 14%) was obtained as a white solid (mp 125- 130 0 C).
  • the reaction mixture was added with saturated ammonium chloride solution (30 mL) and then extracted with ethyl acetate (50 mL). The organic phase was washed with saturated sodium chloride solution (three times 40 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by recrystallization from hexane / methylene chloride. The target compound (110 mg, 25%) was obtained as a yellow solid.
  • reaction mixture was added with methanol (10 mL) and saturated ammonium chloride solution (15 mL) and then extracted with ethyl acetate (20 mL). The organic phase was washed with saturated sodium chloride solution (three times 20 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 13: 2 methylene chloride /
  • the reaction mixture was added with saturated ammonium chloride solution (15 mL) and then extracted with ethyl acetate (20 mL). The organic phase was washed with saturated sodium chloride solution (three times 20 mL each time), dried with sodium sulfate and freed from the solvent. The residue was purified by column chromatography (silica gel, 3: 1 to 1: 1 hexane / ethyl acetate). The target compound (120 mg, 55%) as a yellow solid was obtained.
  • Example I-8 Synthesis of thiocarbonic acid ⁇ 2- [Rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) -oxiranylmethyl] -2H- [1,2,4] triazole-3 -yl ⁇ ester methyl ester 150 mg 1 - [rel- (2S, 3R) -3- (2-chlorophenyl) -2- (3-fluorophenyl) oxiran-2-ylmethyl] -1H - 1, 2,4- Triazole-5 (4H) -thione was dissolved in 5 ml of THF and treated at room temperature with 7 mg of sodium hydride.
  • Example 1-11 Analogously to Example 1-10, the compound 1-11 can be prepared starting from the corresponding starting materials:
  • the active ingredients were formulated separately or together as stock solution with a concentration of 10,000 ppm in DMSO.
  • Orysastrobin was used as a commercial formulation and diluted with respect to the active ingredient with water!
  • the determined values (measured parameters) for the percentage infestation on the leaves were compared with the growth of the active ingredient-free control variant and the fungus-free and active ingredient-free blank value in order to determine the relative growth in% of the
  • the efficiency (W) is calculated according to the formula of Abbot as follows:
  • W (1- ⁇ / ⁇ ) 100 ⁇ corresponds to the fungal infestation of the treated plants in% and ⁇ corresponds to the fungal infestation of the untreated (control) plants in%
  • the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous pea-based zoospore suspension of Phytophthora infestans.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. Subsequently, a malt-based aqueous spore suspension of Botrytis cinerea was added. The plates were placed in a steam-saturated chamber at temperatures of 18 ° C established. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • MTP microtiter plate
  • MTP microtiter plate
  • a malt-based aqueous spore suspension of Pyricularia oryzae was added.
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous spore suspension based on malt of Septoria tritici.
  • MTP microtiter plate
  • the plates were placed in a water vapor-saturated chamber at temperatures of 18 C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne des mélanges fongicides contenant comme constituants actifs 1) des azolylméthyloxiranes de formule générale (I), dans laquelle les variables ont les significations décrites dans la demande, 2) un composé fongicide II et 3) éventuellement un autre composé fongicide II, les composés Il des constituants 2 et 3 étant sélectionnés indépendamment l'un de l'autre parmi les composés décrits dans la demande, dans la mesure où les constituants 2 et 3 ne sont pas identiques, ainsi que l'utilisation des mélanges fongicides dans la lutte contre les champignons phytopathogènes et des produits contenant lesdits mélanges.
PCT/EP2010/058339 2009-06-16 2010-06-15 Mélanges fongicides Ceased WO2010146029A2 (fr)

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EP2746260A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
US9717797B2 (en) 2013-12-05 2017-08-01 International Business Machines Corporation Polycarbonates bearing aromatic N-heterocycles for drug delivery
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
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CN116349685A (zh) * 2021-12-27 2023-06-30 沈阳中化农药化工研发有限公司 一种含细胞骨架和运动蛋白抑制剂类杀菌剂的杀真菌组合物及其应用

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2746260A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
US9717797B2 (en) 2013-12-05 2017-08-01 International Business Machines Corporation Polycarbonates bearing aromatic N-heterocycles for drug delivery
US10610597B2 (en) 2013-12-05 2020-04-07 International Business Machines Corporation Polycarbonates bearing aromatic N-heterocycles for drug delivery
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
CN116349685A (zh) * 2021-12-27 2023-06-30 沈阳中化农药化工研发有限公司 一种含细胞骨架和运动蛋白抑制剂类杀菌剂的杀真菌组合物及其应用
CN115321949A (zh) * 2022-08-30 2022-11-11 山西始耳趾电子科技有限公司 一种高光抗菌瓷砖及其生产工艺

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