WO2015181035A1 - Mélanges fongicides à base de dérivés de 1,4-dithiine - Google Patents

Mélanges fongicides à base de dérivés de 1,4-dithiine Download PDF

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WO2015181035A1
WO2015181035A1 PCT/EP2015/061211 EP2015061211W WO2015181035A1 WO 2015181035 A1 WO2015181035 A1 WO 2015181035A1 EP 2015061211 W EP2015061211 W EP 2015061211W WO 2015181035 A1 WO2015181035 A1 WO 2015181035A1
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iii
methyl
phenyl
chloro
inhibitors
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PCT/EP2015/061211
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English (en)
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Wassilios Grammenos
Nadege Boudet
Bernd Mueller
Maria Angelica QUINTERO PALOMAR
Ana Escribano Cuesta
Thomas Grote
Marcus Fehr
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Basf Se
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    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to mixtures comprising, as active components,
  • the present invention relates to an agrochemical composition, comprising an auxiliary and the mixture.
  • the present invention relates to an agrochemical composition, further comprising as component 3) a further active compound.
  • the present invention relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the fungicidal mixture or the composition.
  • the present invention relates to plant propagation material comprising the inventive mixture or the inventive composition in an amount of from 0.01 g to 10 kg per 100 kg of plant propagation material.
  • Another typical problem arising in the field of pest control lies in the need to reduce the dosage rates of the active ingredient in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective pest control.
  • It is an object of the present invention overcome the abovementioned disadvantages and to provide, with a view to effective resistance management and effective control of phytopathogenic harmful fungi, insects or other pests or to effective plant growth regulation, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi, insects or other pests or improved plant growth regulating activity (synergistic mixtures) and a broadened activity spectrum, in particular for certain indications.
  • the invention can also result in an advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage stability and light stability, advantageous residue formation, improved toxicological or ecotoxicological behaviour, improved properties of the plant, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, lower phytotoxicity, mobilization of the defense system of the plant, good compatibility with plants.
  • the invention can also result in an advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage stability and light stability, advantageous residue formation, improved toxicological or ecotoxicological behaviour, improved properties of the plant, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, lower phytotoxicity, mobilization of the defense system of the plant, good compatibility with plants.
  • the present invention relates to mixtures comprising, as active components,
  • Inhibitors of complex III at Q 0 site e. g. strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxy- strobin, fluoxastrobin, kresoxim-methyl, mandestrobine, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-(2-(3-(2,6-di- chlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone, methyl-A/-[2- [
  • inhibitors of complex II e. g. carboxamides: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N- (2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, N-(2- (1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim, (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine; nitro- phenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;
  • C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole, bitertanol, bromucona- zole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbu- conazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triti- conazole, uniconazole,
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
  • hymexazole octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
  • D) Inhibitors of cell division and cytoskeleton tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuber- idazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7-(4-methyl- piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine
  • diethofencarb diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil; protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
  • MAP / histidine kinase inhibitors fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
  • G protein inhibitors quinoxyfen
  • Phospholipid biosynthesis inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane; lipid peroxidation: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • phospholipid biosynthesis and cell wall deposition dimethomorph, flumorph, mandipropa- mid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1-(1-(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
  • fatty acid amide hydrolase inhibitors oxathiapiprolin, 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoromethyl-1 H- pyrazol-1-yl]acetyl ⁇ piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ phenyl me- thanesulfonate, 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoromethyl)-1 H-pyrazol-1-yl]acetyl ⁇ piperidin-4-yl) 1 ,3- thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ -3-chlorophenyl methanesulfonate;
  • inorganic active substances Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles: anilazine, chloro- thalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pen- tachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4- methyl-benzenesulfonamide; guanidines and others: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl- 1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']di
  • inhibitors of glucan synthesis validamycin, polyoxin B; melanin synthesis inhibitors: pyroqui Ion, tricyclazole, carpropamid, dicyclomet, fenoxanil;
  • acibenzolar-S-methyl probenazole, isotianil, tiadinil, prohexadione-calcium
  • phosphonates fosetyl, fosetyl-aluminum, phosphorous acid and its salts
  • Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus alti- tudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans,
  • Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium ox- ysporum, Clonostachys rosea f. catenulate also named Gliocladium catenulatum
  • Glio- cladium roseum Lysobacter antibioticus
  • L. enzymogenes Metschnikowia fructicola, Mi- crodochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus polymyxa, P.
  • Pseudozyma flocculosa Pichia anomala, Pythium oligandrum, Sphaerodes myco- parasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);
  • Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity chitosan (hydrolysate), harpin protein, laminarin, Menhaden fish oil, natamycin, Plum pox virus coat protein, potassium or sodium bicarbonate, Reynoutria sachalinensis extract, salicylic acid, tea tree oil;
  • Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity Ag- robacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B.
  • brongniartii Burkholderia spp., Chromobacterium subtsugae, Cyd- ia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavo- bacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var.
  • Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity Azospirillum amazonense, A. brasilense, A. lipofer- um, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liao- ningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizo- bium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium meliloti;
  • Biochemical pesticides with plant stress reducing, plant growth regulator and/or plant yield enhancing activity abscisic acid, aluminium silicate (kaolin), 3-decen-2-one, formononetin, genistein, hesperetin, homobrassinolide, humates, jasmonic acid and its salts or derivatives thereof, lysophosphatidyl ethanolamine, naringenin, polymeric polyhydroxy acid, Ascophyllum nodosum (Norwegian kelp, Brown kelp) extract and Ecklonia maxima (kelp) extract;
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6- dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohex- adione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-i
  • acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefe- nacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • amino acid derivatives bilanafos, glyphosate, glufosinate, sulfosate;
  • - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • Bipyridyls diquat, paraquat;
  • (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thio- bencarb, triallate;
  • cyclohexanediones butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepralox- ydim, tralkoxydim; dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
  • diphenyl ethers acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, ox- yfluorfen;
  • hydroxybenzonitriles bomoxynil, dichlobenil, ioxynil;
  • - imidazolinones imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlor- prop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
  • pyrazines chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;
  • pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfu- ron, triflusulfuron, tritosul
  • triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam, trifludimoxazin;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrim- isulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyri- fos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethi- on, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phentho- ate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosul- fan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodi- carb, triazamate;
  • pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • insect growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cy- ramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juve- noids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • nicotinic receptor agonists/antagonists compounds clothianidin, dinotefuran, flupyradi- furone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-2-chloro-thiazol- 5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
  • GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1 H-pyrazole-3-carbothioic acid amide;
  • macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • mitochondrial electron transport inhibitor I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
  • METI II and III compounds acequinocyl, fluacyprim, hydramethylnon; Uncouplers: chlorfenapyr;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite; moulting disruptor compounds: cryomazine;
  • mixed function oxidase inhibitors piperonyl butoxide
  • ryanodine receptor inhibitors chlorantraniliprole, cyantraniliprole, flubendiamide, N-[4,6- dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4- sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyr
  • the present invention provides agrochemical compositions, comprising an auxiliary and the mixture.
  • the present invention provides agrochemical compositions, further comprising as component 3) a further active compound.
  • the present invention provides a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the fungicidal mixture or the composition.
  • the present invention provides plant propagation material comprising the inventive mixture or the inventive composition in an amount of from 0.01 g to 10 kg per 100 kg of plant propagation material.
  • the terms used for organic groups in the definition of the variables are, for example the expression "halogen", collective terms which represent the individual members of these groups of organic units.
  • the prefi 6 Cx-Cy denotes the number of possible carbon atoms in the particular case.
  • alkyl and the alkyl moieties of composite groups such as, for example, alkoxy, alkylamino, alkoxycar- bonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 10 carbon atoms, for example Ci-Cio-akyl, 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
  • haloalkyi straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as men- tioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine.
  • the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (CrC3)-haloalkyl more preferably (Ci-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichlorome- thyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoro- methyl, chlorodifluoromethyl, 1 -chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1 ,1 , 1-trifluoroprop-2-yl;
  • alkenyl and also the alkenyl moieties in composite groups such as alkenyloxy: unsaturated straight- chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one double bond in any position.
  • alkenyloxy unsaturated straight- chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one double bond in any position.
  • small alkenyl groups such as (C2-C4)- alkenyl
  • larger alkenyl groups such as (Cs-Cs)- alkenyl.
  • alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1 - butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2- dimethyl-1 -propenyl, 1 ,2-dimethyl-2-
  • alkynyl and the alkynyl moieties in composite groups straight-chain or branched hydrocarbon groups having 2 to 10 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1- pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3- butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3- hexynyl, 4-hexyny
  • cycloalkyl and also the cycloalkyl moieties in composite groups mono- or bicyclic saturated hydrocarbon groups having 3 to 10, in particular 3 to 6, carbon ring members, for example C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • optionally substituted Cs-Cs-cycloalkyl means a cycloalkyl radical having from 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1 , 2, 3, 4 or 5 hydrogen atoms, is/are replaced by substituents which are inert under the conditions of the reaction.
  • substituents which are inert under the conditions of the reaction.
  • inert substituents are CN, Ci-C6-alkyl, CrC4-haloalkyl, CrC6-alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-CrC6-alkyl;
  • halocycloalkyi and the halocycloalkyi moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like monocyclic saturated hydrocarbon groups having 3 to 10 carbon ring members (as mentioned above) in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • cycloalkenyl monocyclic monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1 -yl, cy- clohexen-3-yl, cyclohexen-4-yl and the like.
  • the fungicidal mixtures comprise a compound of the formula I in which R is, according to one embodiment, Ci-Cio-alkyl.
  • R is Ci-Cio-alkyl, preferrerably methyl, ethyl, n-propyl, i-propyl, n- butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R is Ci-Cio-haloalkyl; preferrably fully or partially halogenated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular fully or partially halogenated methyl.
  • R is CF3.
  • R is CHF 2 .
  • R is CFH 2 .
  • R is CH 2 CF 3 .
  • R is CC .
  • R is CHCI2.
  • R is CCIH 2 .
  • R is C 2 -Cio-alkenyl, preferably C 2 -C4-alkenyl.
  • R is vinyl.
  • R is
  • CH 2 C(CH3) C(CH3)2.
  • R is C 2 -Cio-alkynyl, preferably C 2 -C4-alkynyl.
  • R is ethynyl.
  • R is 1- propynyl.
  • R is 2-propynyl.
  • R is 1-butynyl.
  • R is 3-methyl-but-1-ynyl.
  • R is C3-Cio-cycloalkyl, preferably is C3-C6-cycloalkyl.
  • R is cyclopropyl.
  • R is cyclopentyl.
  • R is C3-Cio-halocycloalkyl, preferrably fully or partially halogenat- ed cyclopropyl, cyclobutyl, cyclopentyl, in particular fully or partially halogenated cyclopropyl.
  • R is 1 -CI-cyclopropyl.
  • R is 2-CI- cyclopropyl.
  • R is 1-F-cyclopropyl.
  • R is 2-F-cyclopropyl.
  • R is fully or partially halogenated cyclobutyl.
  • R is 1-CI-cyclobutyl.
  • R is 1-F- cyclobutyl. In a further special embodiment R is 2-CI-cyclobutyl. In a further special embodiment R is 3-CI-cyclobutyl. In a further special embodiment R is 2-F-cyclobutyl. In a further special embodiment R is 3-F-cyclobutyl. In a further special embodiment R1 is 3,3-(CI) 2 -cyclobutyl. In a further special embodiment R1 is 3,3-(F) 2 -cyclobutyl.
  • R is C3-Cio-cycloalkenyl, preferably cyclopropenyl.
  • the active compounds II mentioned above as component 2 are pesticide.
  • a pesticide is generally a chemical or biological agent (such as a virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:
  • Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
  • Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.
  • Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.
  • Biopesticidal seed treatments are e. g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed.
  • Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves ("greening effect")
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • biopesticides under certain conditions can also have disadvantages such as high specificity: which may require an exact identification of the pest/pathogen and the use of multiple products to be used, slow speed of action (thus making them unsuitable if a pest outbreak is an immediate threat to a crop), variable efficacy due to the influences of various biotic and abiotic factors (since biopesticides are usually living organisms, which bring about pest/pathogen control by multiplying within the target insect pest/pathogen) and resistance development.
  • the mixtures comprise as compounds II fungicidal compounds that are independently of each other selected from the groups A), B), C), D), E), F), G), H), I), J), K) and L).
  • mixtures comprise as compound III a herbi- cidal compound that is selected from the group N).
  • mixtures comprise as compound II an insecticidal compound that is selected from the group O).
  • mixtures comprise as compound II (component 2) at least one active substance selected from group A) and particularly selected from azoxystrobin, fluoxastrobin, picoxystrobin, trifloxystrobin; famoxadone, fenamidone; fluopyram, isopyrazam, penflufen, penthiopyrad, sedaxane; cyazofamid, fluazinam, fentin salts, such as fentin acetate.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group B) and particularly selected from cyproconazole, flusilazole, flutriafol, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, fenarimol, triforine; dodemorph, tridemorph, fenpropidin, spiroxamine; fenhexamid.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group C) and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group D) and particularly selected from benomyl, carbendazim, thi- ophanate-methyl, ethaboxam, fluopicolide, zoxamide, pyriofenone.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group E) and particularly selected from cyprodinil, mepanipyrim, py- rimethanil.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group F) and particularly selected from iprodione, fludioxonil, quinoxyfen.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group G) and particularly selected from flumorph, iprovalicarb, ben- thiavalicarb, mandipropamid, propamocarb.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group H) and particularly selected from copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, mancozeb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group I) and particularly selected from carpropamid and fenoxanil.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group J) and particularly selected from acibenzolar-S-methyl, pro- benazole, tiadinil, fosetyl, fosetyl-aluminium, H3PO3 and salts thereof.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group K) and particularly selected from cymoxanil, proquinazid and N- methyl-2- ⁇ 1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl ⁇ -A/-[(1 R)-1 ,2,3,4- tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide.
  • mixtures comprise as compound II (component 2) at least one active substance selected from group L) and particularly selected from Bacillus pumilus strain NRRL No. B-30087 and Ulocladium oudemansii .
  • Compounds I and/or the pesticides II can be present in different crystal modifications, which may differ in biological activity.
  • pesticides II selected from groups L1 ), L3) and L5) in the mixtures embraces not only the isolated, pure cultures of the respective microorganisms as defined herein, but also its cell-free extract having pesticidal activity, preferably a ketone-based extract, its suspensions in a whole broth culture or as a metabolite-containing supernatant or a purified metabolite obtained from a whole broth culture of the microorganism or microorganism strain.
  • Whole broth culture refers to a liquid culture containing both cells and media.
  • Supernatant or “culture medium” refers to the liquid broth remaining when cells grown in broth are removed by centrifugation, filtration, sedimentation, or other means well known in the art.
  • metabolite refers to any compound, substance or byproduct (including but not limited to small molecule secondary metabolites, polyketides, fatty acid synthase products, non- ribosomal peptides, ribosomal peptides, proteins and enzymes) produced by a microorganism (such as fungi and bacteria) that has pesticidal activity or improves plant growth, water use efficiency of the plant, plant health, plant appearance, or the population of beneficial microorganisms in the soil around the plant activity.
  • a microorganism such as fungi and bacteria
  • mutant refers a microorganism, obtained by direct mutant selection but also includes microorganisms that have been further mutagenized or otherwise manipulated (e. g., via the introduction of a plasmid). Accordingly, embodiments include mutants, variants, and or derivatives of the respective microorganism, both naturally occurring and artificially induced mutants. For example, mutants may be induced by subjecting the microorganism to known mutagens, such as N-methyl-nitrosoguanidine, using conventional methods. Preferably such mutants retain the pesticidal activity of the respective microorganism.
  • the mixtures comprise compound of the formula I and at least one pesticide II in a synergistically effective amount.
  • the invention also relates to a method for controlling phytopathogenic harmful fungi using mixtures of compound of the formula I and at least one pesticide I I and to the use of compound of the formula I and pesticides II for preparing such mixtures, and to compositions comprising these mixtures and seed comprising these mixtures or coated with this this mixture.
  • compositions according to the invention are compiled in Table B, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B Two-component compositions comprising one component I and as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • mixtures and compositions thereof according to the invention can, in the use form as fungicides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immediately prior to use (tank mix).
  • active substances e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immediately prior to use (tank mix).
  • mixtures and compositions thereof according to the invention can, in the use form as fungi- cides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immediately prior to use (tank mix).
  • active substances e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immediately prior to use (tank mix).
  • the mixtures comprise besides one compounds l-A to l-l and one pesticide II and a further active ingredient (e. g. pesticide III as component 3), preferably in a synergistically effective amount.
  • a further active ingredient e. g. pesticide III as component 3
  • Another embodiment relates to mixtures wherein the component 3) is a pesticide III selected from groups A) to O):
  • strobilurins e. g. strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxy- strobin, fluoxastrobin, kresoxim-methyl, mandestrobine, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-(2-(3-(2,6-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone,
  • - inhibitors of complex II e. g. carboxamides: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2- (1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide,
  • complex II e. g. carboxamides: benodanil, benzovindiflupyr, bixafen,
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim, (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine; nitro- phenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal com- pounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;
  • SBI fungicides Sterol biosynthesis inhibitors
  • DMI fungicides C14 demethylase inhibitors: triazoles: azaconazole, bitertanol, bromucona- zole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbu- conazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triti- conazole, uniconazole,
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
  • hymexazole hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuber- idazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7-(4-methyl- piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine
  • cell division inhibitors diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
  • blasticidin-S blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
  • - Phospholipid biosynthesis inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane;
  • lipid peroxidation dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • phospholipid biosynthesis and cell wall deposition dimethomorph, flumorph, mandipropa- mid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
  • oxathiapiprolin oxathiapiprolin
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles: anilazine, chloro- thalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pen- tachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4- methyl-benzenesulfonamide;
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles
  • guanidine dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl- 1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone;
  • glucan synthesis validamycin, polyoxin B; melanin synthesis inhibitors: pyroqui- lon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, di- methipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadi- one (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phos- phorotrithioate, 2,3,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefe- nacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • EPTC esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thio- bencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, ox- yfluorfen;
  • - phenoxy acetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlor- prop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • - sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfu- ron, triflusulfuron, trito
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam, trifludimoxazin;
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrim- isulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyri- fos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethi- on, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phentho- ate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosul- fan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodi- carb, triazamate;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • - insect growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cy- ramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juve- noids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • - nicotinic receptor agonists/antagonists compounds clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -2-chloro-thiazol-5- ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
  • - GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole,
  • - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • cryomazine cryomazine
  • - mixed function oxidase inhibitors piperonyl butoxide
  • - sodium channel blockers indoxacarb, metaflumizone
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci.
  • pesticides II and/or III of chemical nature described by their common names, their preparation and their biological activity e. g. against harmful fungi, pests or weed is known (cf.:
  • the mixtures comprise as pesticides III fungicidal compounds that are independently of each other selected from the groups A), B), C), D), E), F), G), H), I), J), K), L1 ) and L2).
  • mixtures comprise as pesticide III (component 3) a herbicidal compound that is selected from the group N.
  • mixtures comprise as pesticide III (component 3) an insecti- cidal compound that is selected from the group O).
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group A) and particularly selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin; fa- moxadone, fenamidone; benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyra- zam, penflufen, penthiopyrad, sedaxane; ametoctradin, cyazofamid, fluazinam, fentin salts, such as fentin acetate.
  • azoxystrobin dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group B) and particularly selected from cyproconazole, difenocona- zole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, pen- conazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetracona- zole, triticonazole, prochloraz, fenarimol, triforine; dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine; fenhexamid.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group C) and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group D) and particularly selected from benomyl, carbendazim, thi- ophanate-methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group E) and particularly selected from cyprodinil, mepanipyrim, py- rimethanil.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group F) and particularly selected from iprodione, fludioxonil, vin- clozolin, quinoxyfen.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group G) and particularly selected from dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid, propamocarb.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group H) and particularly selected from copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, mancozeb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group I) and particularly selected from carpropamid and fenoxanil.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group J) and particularly selected from acibenzolar-S-methyl, pro- benazole, tiadinil, fosetyl, fosetyl-aluminium, H3PO3 and salts thereof.
  • mixtures comprise as pesticide III (component 3) at least one active substance selected from group K) and particularly selected from cymoxanil, proquinazid and N- methyl-2- ⁇ 1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl ⁇ -A/-[(1 R)-1 ,2,3,4- tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide.
  • the biopesticides from group L) of pesticides II, their preparation and their pesticidal activity e. g. against harmful fungi or insects are known (e-Pesticide Manual V 5.2 (ISBN 978 1 901396 85 0) (2008-201 1 );
  • compositions according to the invention i.e. one specific individualized composition.
  • these are ternary compositions which each only contain these three components as the active compound.
  • every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table T1 Three-component compositions comprising a component I, a component II a component III, wherein component II and III are selected from the preferred fungicides detailled above, wherein components II and III are different from each other.
  • Table 1 Ternary mixtures T-1 to T-396 comprising one compound I as defined and numbered above as component 1 ) (Co. 1 ) and one compound II as defined and numbered above as component 2) (Co. 2) and one compound III from groups A) to L) as defined and numbered in Table B as component 3) (Co. 3).

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Abstract

La présente invention concerne des mélanges fongicides à base de dérivés de 1,4-dithiine de formule (I). L'invention concerne également un procédé permettant de lutter, à l'aide de tels mélanges, contre des champignons nuisibles présents sur des végétaux cultivés.
PCT/EP2015/061211 2014-05-30 2015-05-21 Mélanges fongicides à base de dérivés de 1,4-dithiine WO2015181035A1 (fr)

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WO2016166020A1 (fr) * 2015-04-16 2016-10-20 Basf Se Atténuation de phytotoxicité de fongicides multisites par des dispersants à poids moléculaire élevé
WO2017157910A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des céréales
WO2017157915A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des céréales en tant que traitement de semences
WO2017157923A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des plantes agricoles
WO2017157916A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur le soja
WO2017157920A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des fruits
US10053432B2 (en) 2013-12-12 2018-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10450279B2 (en) 2014-06-06 2019-10-22 Basf Se Substituted [1,2,4]triazole compounds
US10499644B2 (en) 2015-11-19 2019-12-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10555526B2 (en) 2015-11-05 2020-02-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10645942B2 (en) 2018-04-30 2020-05-12 Stoller Enterprises, Inc. Synergistic formulation including at least one gibberellin compound and salicyclic acid
US10674727B2 (en) 2015-11-19 2020-06-09 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10696634B2 (en) 2015-12-01 2020-06-30 Basf Se Pyridine compounds as fungicides
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
US10785980B2 (en) 2016-06-09 2020-09-29 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10986839B2 (en) 2016-04-11 2021-04-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2022128812A1 (fr) 2020-12-17 2022-06-23 Basf Se Compositions de spores, leur production et leurs utilisations

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US20110064827A1 (en) * 2009-09-14 2011-03-17 Bayer Cropscience Ag Active compound combinations
US20140045687A1 (en) * 2011-04-15 2014-02-13 Basf Se Use of substituted dithiine-dicarboximides for combating phytopathogenic fungi
WO2014009137A1 (fr) * 2012-07-13 2014-01-16 Basf Se Thiadiazoles substitués et leur utilisation comme fongicides
WO2014086601A1 (fr) * 2012-12-04 2014-06-12 Basf Se Dérivés substitués inédits de 1,4-dithiine et leur utilisation en tant que fongicides

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10053432B2 (en) 2013-12-12 2018-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10450279B2 (en) 2014-06-06 2019-10-22 Basf Se Substituted [1,2,4]triazole compounds
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
WO2016166020A1 (fr) * 2015-04-16 2016-10-20 Basf Se Atténuation de phytotoxicité de fongicides multisites par des dispersants à poids moléculaire élevé
US10555526B2 (en) 2015-11-05 2020-02-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10499644B2 (en) 2015-11-19 2019-12-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10674727B2 (en) 2015-11-19 2020-06-09 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10696634B2 (en) 2015-12-01 2020-06-30 Basf Se Pyridine compounds as fungicides
WO2017157920A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des fruits
WO2017157916A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur le soja
WO2017157923A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des plantes agricoles
WO2017157915A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des céréales en tant que traitement de semences
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
WO2017157910A1 (fr) * 2016-03-16 2017-09-21 Basf Se Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des céréales
RU2754614C2 (ru) * 2016-03-16 2021-09-03 Басф Се Применение тетразолинонов для борьбы с устойчивыми фитопатогенными грибами на злаковых культурах
US10905122B2 (en) 2016-03-16 2021-02-02 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
US10986839B2 (en) 2016-04-11 2021-04-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10785980B2 (en) 2016-06-09 2020-09-29 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
US10645942B2 (en) 2018-04-30 2020-05-12 Stoller Enterprises, Inc. Synergistic formulation including at least one gibberellin compound and salicyclic acid
WO2022128812A1 (fr) 2020-12-17 2022-06-23 Basf Se Compositions de spores, leur production et leurs utilisations

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