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WO2011026796A1 - Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi - Google Patents

Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi Download PDF

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WO2011026796A1
WO2011026796A1 PCT/EP2010/062565 EP2010062565W WO2011026796A1 WO 2011026796 A1 WO2011026796 A1 WO 2011026796A1 EP 2010062565 W EP2010062565 W EP 2010062565W WO 2011026796 A1 WO2011026796 A1 WO 2011026796A1
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methyl
chloro
phenyl
acid
compounds
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French (fr)
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Markus Frank
Thorsten Jabs
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BASF SE
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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
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids

Definitions

  • Synergistic fungicidal mixtures comprising lactylates and method for combating phyto- pathogenic fungi
  • the present invention relates to a mixture, comprising as active compounds
  • Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms, wherein the carbon chain is branched or unbranched,
  • X is H or CHs; n is an integer with a value of 1 to 10;
  • A is, if n > 1 , -CO-, or,
  • azoxystrobin dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, me- tominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2-methyl-phen- oxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane-carboximidoyl- sulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2-chloro-5-[1 -(3- methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2-(3-(
  • carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino- 4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoride
  • - benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide;
  • carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
  • - triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenocona- zole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquin- conazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4-chloro-phenyl)-2- ([1 ,2,4]triazol-1 -yl)-cycloheptanol;
  • - pyridines fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3- yl]-pyridine, 2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro- pyridine-2,6-di-carbonitrile, N-(1 -(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloronicotinamide, N-[(5-bromo-3-chloro-pyridin-2-yl)-methyl]-2,4-dichloro- nicotinamide;
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;
  • dicarboximides fluoroimid, iprodione, procymidone, vinclozolin;
  • non-aromatic 5-membered heterocycles famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro- pyrazole-1 -carbothioic acid S-allyl ester; - others: acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzo- quat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, pro- quinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iod
  • guanidine guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
  • antibiotics kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, polyoxine, validamycin A;
  • - nitrophenyl derivates: binapacryl, dinobuton, dinocap, nitrthal-isopropyl,
  • organometal compounds fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
  • organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, ipro- benfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
  • organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusul- famide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, flu- thiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohy- drojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • - (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • - phenoxy acetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4- DB, dichlorprop, 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, flu- cetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodo- sulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, ox- asulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometu- ron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, trito
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, tri- aziflam;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyriben- zoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyri- fos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme- thrin, 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: chlorflua- mecanicon, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spi- romesifen, spirotetramat;
  • nicotinic receptor agonists/antagonists compounds clothianidin, dinotefuran, 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, pyra- fluprole, 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, le- pimectin, spinosad, spinetoram;
  • - mitochondrial electron transport inhibitor I acaricides: fenazaquin, pyri- daben, tebufenpyrad, tolfenpyrad, flufenerim;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • cryomazine cryomazine
  • the present invention furthermore relates to a method for combating phy- topathogenic harmful fungi, which process comprises treating the fungi or the plants, the soil or seeds to be protected against fungal attack, with an effective amount of the mixtures as defined herein.
  • the present invention also relates to an agrochemical composition which comprises a solvent or solid carrier and a mixture as defined herein.
  • the present invention also relates to seed coated with a mixture as defined herein or a composition thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
  • Another typical problem arising in the field of pathogen control lies in the need to reduce the dosage rates of the fungicides in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing pathogen control.
  • a further problem encoutered concerns the need to have available fungal control agents which show an improved action against harmful fungi with a reduced amount of active compounds applied and/or a broadened spectrum of pathogens controlled.
  • Another difficulty in relation to the use of fungicides is that the repeated and exclusive application of an individual pesticidal compound or compounds of the same mode of action or chemical class leads in many cases to a rapid selection of fungal pathogens that have developed natural or adapted resistance against the active compound or chemical class in question.
  • Lactylates such as sodium stearoyl lactylate are well-known and safe cosmetic and food additives e.g. used as a dough strengthener in baked goods or as emulsifiers in cleansing products or as hair conditioner.
  • WO 2009/092787 describes an anti-bacterial animal feed composition comprising lactylates and/or glycolylates.
  • An animal feed composition is described as being active against gram-positive bacteria in animals. The use for treating or preventing intestinal infections with Clostridium perfringens in animals is specified. While the anti-bacterial activity is elucidated, their efficacy against fungi and specifically against phytopathogenic fungi is not mentioned. There is nothing in this reference that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in
  • US 2009/0082253 A1 relates to an antibacterial composition comprising lactylates and to its use as antibacterial agent active against gram-negative bacteria e.g. in the pharmaceutical field, in the feed industry and in the food and drink industry.
  • the reduction or prevention of gram-negative human pathogenic bacteria such as Escherichia coli, Salmonella typhimurium and S. enteridis is specified.
  • GB1 1 15480 suggests the use of acyated alpha-hydroxy carboxylic acids for food conservation and reduction of skin diseases.
  • the compositions described for consumption by or application to humans or other animals have been shown to be active against human pathogenic bacteria and molds e.g. on packaged cheese or leather. There is nothing in these references that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in agrochemical compositions.
  • WO 2006/006788 describes a fungicidally active composition of anhydrous milk fat as fungicidally active component and an emulsifier and an antioxidant such as .
  • an emulsifier such as calcium stearoyi lactylate is used as an emulsifier for the milk fat and a mixture of propyl gallate and citric acid monoglyceride ester as an antioxidant.
  • lactylates are however, not known to be effective against phytopathogenic fungi or to form synergistically effective mixtures for the control of phytopathogenic fungi. They are therefore also not used as fungicidal agents in agrochemical compositions. In fact, their regulatory status is that of of them being used as
  • Agriculturally useful salts of the compounds I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammo- nium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfo- nium ions, preferably tri(Ci-C4-alkyl)sulfonium,
  • an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms refers to a univalent acyl radical [RCO] from a Ci-C34-alkyl carboxylic acid or from a Ci-C34-alkenyl carboxylic acid with a straight-chained or branched saturated or unsaturated (having at least one double bond) hydrocarbon group, for example bu- tanoyl, butenoyl, hexanoyl (caproyl) (Ce), octoyl (capryloyl) (Cs), lauroyl (C12), myristoyl (C14), hexadecanoyl (palmitoyl) (C16), stearoyi (ds), oleoyl (C18, C18: 1 ), linoleoyl (Cis, C1 8:2), linolenoyl (Cie, C18:
  • lactylates or glycolylates of formula I preference is given to lactylates or glycolylates of formula I (compounds I) wherein A is -CO-.
  • the use of glycolylates of formula I, wherein A is -CO- and X is H is preferred.
  • Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-20 carbon atoms. More in particular, Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-1 8 carbon atoms.
  • suitable substituents include acyl groups having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 1 0 carbon atoms (decanoyl), 12 carbon atoms (lauroyl), 14 carbon atoms (myristoyl), 1 6 carbon atoms (palmitoyl), 18 carbon atoms (stearoyi). Mixtures of two or more com- pounds may also be used.
  • More preferred substituents Ac are selected from acyl radicals of an alkyl or alkenyl carboxylic acid having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 10 carbon atoms (decanoyl), 12 carbon atoms (lauroyl) and 14 carbon atoms (myristoyi).
  • salt of compounds of formula I the use of a Na, K, Ca, Mg, Fe(ll), Zn, NH4, or Cu(ll) salt may be preferred with a Na, K, Ca, or Mg salt being particularly preferred.
  • n is preferably in the range of 1 -5. More preferably, n has a value of 1 , 2, or 3, in particular n is 2.
  • lauroyl lactylate, myristoyi lactylate, and their sodium salts is particularly preferred.
  • a mixture is used comprising 5-95 wt.% of lauroyl lactylate and 95-5 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds are used, more in particular, a mixture is used comprising 25-75 wt. %, more in particular 40-60 wt. % of lauroyl lactylate, and 75-25 wt.%, more in particular 40-60 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds.
  • epoxiconazole (2RS,3SR)-1 -[3-(2-chloro- phenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1 H-1 ,2,4-triazole (EP-A 196 038); fenbu- conazole, a -[2-(4-chlorophenyl)ethyl]-a -phenyl-1 H-1 ,2,4-triazole-1 -propanenitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis. Vol. 1 , p.
  • the mixtures comprise as compound II a compound that is selected from the group A), C), D), E), F) and G).
  • mixtures comprise as compound II a compound that is selected from the group H).
  • mixtures comprise as compound II a compound that is selected from the group I).
  • mixtures comprise as compound II a compound of group A (strobilurins), preferably selected from pyraclostrobin, kresoxim-methyl, azoxystrobin, fluoxastrobin, trifloxystrobin, enestroburin and pyribencarb, more preferably from pyraclostrobin and fluoxastrobin.
  • group A strobilurins
  • group B) of compounds II is as follows:
  • - carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, sedaxane, carboxin, penthiopyrad, boscalid, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isoti- anil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, , tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 , 1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3- difluor
  • carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
  • mixtures comprise as compound II a compound of group B (carboxamides), preferably selected from bixafen, penthiopyrad, sedaxane, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl- 1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl- 5-fluoro-1 H-pyrazole-4-carboxamide, fluopyram, mandiproamid
  • mixtures comprise as compound II a compound of group C (azoles), preferably selected from epoxiconazole, prochloraz, ethaboxam, benomyl, carbendazim, thiabendazole, difenoconazole, flusilazole, tebuconazol, cypro- conazole, prothioconazole and 1 -(4-chloro-phenyl)-2-([1 ,2,4]triazol-1 -yl)-cycloheptanol, more preferably selected from epoxiconazole and prothioconazole.
  • azoles preferably selected from epoxiconazole, prochloraz, ethaboxam, benomyl, carbendazim, thiabendazole, difenoconazole, flusilazole, tebuconazol, cypro- conazole, prothioconazole and 1 -(4-chloro
  • mixtures comprise as compound II a compound of group D (heterocyclic compounds), preferably selected from famoxadone, fenami- done, folpet, captan and 5-amino-2-isopropyl-3-oxo-4-o-tolyl-2,3-dihydro-pyrazole- 1 -carbothioic acid S-allyl ester.
  • group D heterocyclic compounds
  • the mixtures comprise at least one compound (II) selected from the group of E) carbamates, more preferably selected from man- cozeb, maneb and metiram.
  • mixtures comprise as compound II a compound of group F (other active substances), preferably selected from cymoxanil, thiophanate- methyl, fosetyl, chlorothalonil, copper, copper hydroxide and copper oxychloride.
  • group F other active substances
  • the mixtures and compositions according to the invention are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the mixtures and compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • cereals e. g. wheat, rye, barley, triticale, oats or rice
  • beet e. g. sugar beet or fodder beet
  • fruits such as pomes, stone fruits or soft fruits, e. g.
  • inventive mixtures and compositions are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This in- eludes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with the inventive combination of compounds I and compounds II and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • the agrochemical compositions and the fungicidal mixtures, respectively, are particularly suitable for controlling the following fungal plant diseases:
  • Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Bipolaris and Drechslera spp.
  • Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E.
  • graminicola anamorph: Septoria tritici, Septoria blotch
  • M. fijiensis black Sigatoka disease
  • Peronospora spp. downy mildew
  • cabbage e. g. P. brassicae
  • rape e. g. P. para- sitica
  • onions e. g. P. destructor
  • tobacco P. tabacina
  • soybeans e. g. P. P.
  • oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R.
  • mixtures and the compositions thereof are effective against plant pathogens in speciality crops such as vine, fruits, hop, vegetables and tabacco - see the above list.
  • Plant propagation materials may be treated with the mixtures and compositions of the invention prophylactically either at or before planting or transplanting.
  • the present invention also relates to a pesticidal agent comprising at least one solid or liquid carrier and a composition as described herein.
  • the compounds I and compounds II, and salts thereof can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • agrochemical compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the composition type depends on the particular intended purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • composition types are suspensions (SC, OD, FS), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF).
  • SC suspensions
  • FS wettable powders or dusts
  • WP wettable powders or dusts
  • SS SS
  • WS DP
  • DS granules
  • compositions are prepared in a known manner (cf. US 3,060,084,
  • the agrochemical compositions may also comprise auxiliaries which are customary in agrochemical compositions.
  • the auxiliaries used depend on the particular applica- tion form and active substance, respectively.
  • auxiliaries are solvents, solid carriers, dispersants or emulsifi- ers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and anorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment for- mulations).
  • Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g.
  • Solid carriers are mineral earths such as silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, am
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, such as ligninsoulfonic acid (Borresperse ® types, Borregard, Norway) phenolsulfonic acid, naphthalenesulfonic acid (Morwet ® types, Akzo Nobel, U.S.A.), dibutylnaphthalene- sulfonic acid (Nekal ® types, BASF, Germany), and fatty acids, alkylsulfonates, alkyl- arylsulfonates, alkyl sulfates, laurylether sulfates, fatty alcohol sulfates, and sulfated hexa-, hepta- and octadecanolates, sulfated fatty alcohol glycol ethers,
  • aromatic sulfonic acids such as ligninsoulfonic acid (Borresperse
  • methylcellulose g. methylcellulose
  • hydrophobically modified starches polyvinyl alcohols (Mowiol ® types, Clariant, Switzerland), polycarboxylates (Sokolan ® types, BASF, Germany), polyalkoxylates, polyvinyl- amines (Lupasol ® types, BASF, Germany), polyvinylpyrrolidone and the copolymers therof.
  • thickeners i. e. compounds that impart a modified flowability to compositions, i. e. high viscosity under static conditions and low viscosity during agitation
  • thickeners are polysaccharides and organic and anorganic clays such as Xanthan gum (Kelzan ® , CP Kelco, U.S.A.), Rhodopol ® 23 (Rhodia, France), Veegum ® (R.T. Vanderbilt, U.S.A.) or Attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added for preservation and stabilization of the composition.
  • suitable bactericides are those based on dichlorophene and benzyl- alcohol hemi formal (Proxel ® from ICI or Acticide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide ® MBS from Thor Chemie).
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • anti-foaming agents examples include silicone emulsions (such as e. g. Silikon ® SRE, Wacker, Germany or Rhodorsil ® , Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, fluoroorganic compounds and mixtures thereof.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes. Examples to be mentioned und the designations rhodamin B, C. I. pigment red 1 12, C. I. solvent red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • tackifiers or binders examples include polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols and cellulose ethers (Tylose ® , Shin-Etsu, Japan).
  • Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the compounds I and compounds II with at least one solid carrier.
  • Granules e. g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active substances to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e.
  • ammonium sulfate ammonium phosphate, ammonium nitrate, ureas
  • products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of ac- tive substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Water-soluble concentrates (LS), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are usu- ally employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • These compositions can be applied to plant propagation materials, particularly seeds, diluted or undiluted.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before sowing.
  • Methods for applying or treating agrochemical compounds and compositions thereof, respectively, on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting, dusting and soaking application methods of the propagation material.
  • the compounds or the compositions thereof, respectively are applied on to the plant propagation mate- rial by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • a suspension-type (FS) composition is used for seed treatment.
  • a FS composition may comprise 1 -800 g/l of active substance, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • the active substances can be used as such or in the form of their compositions, e. g. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading, brushing, immersing or pouring.
  • the application forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active substances according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
  • concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil and such concentrates are suitable for dilution with water.
  • the active substance concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.001 to 1 % by weight of active substance.
  • the active substances may also be used successfully in the ultra-low-volume proc- ess (ULV), it being possible to apply compositions comprising over 95% by weight of active substance, or even to apply the active substance without additives.
  • UUV ultra-low-volume proc- ess
  • the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active substance per ha.
  • active substance In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 1 to 1000 g, preferably from 5 to 100 g, per 100 kilogram of seed are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, e. g., 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the mixtures or the compositions comprising them, if appropriate not until immediately prior to use (tank mix).
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • Adjuvants which can be used are in particular organic modified polysiloxanes such as Break Thru S 240 ® ; alcohol alkoxylates such as Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ® ; EO/PO block polymers, e. g. Pluronic RPE 2035 ® and Genapol B ® ; alcohol ethoxylates such as Lutensol XP 80 ® ; and dioctyl sulfo- succinate sodium such as Leophen RA ® .
  • organic modified polysiloxanes such as Break Thru S 240 ®
  • alcohol alkoxylates such as Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO/PO block polymers e. g. Pluronic RPE 2035 ® and Genapol B ®
  • compositions 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 immeadiately 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 immeadiately prior to use (tank mix).
  • applying compounds I together with a compound II is to be understood to denote, that compounds I and at least one compound II occur simultaneously at the site of action (i.e. the harmful fungi to be controlled or their habitats such as infected plants, plant propagation materials, particularly seeds, surfaces, mate- rials or the soil as well as plants, plant propagation materials, particularly seeds, soil, surfaces, materials or rooms to be protected from fungal attack) in an effective amount.
  • This can be obtained by applying compounds I and compound II simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s).
  • the order of application is not essential for working of the present invention.
  • the weight ratio of compounds I and compound II generally depends from the properties of the active sub- stances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and particularly in the range of from 1 :5 to 5:1 (compounds I : compound II).
  • the weight ratio of compounds I and compound II is in the range of from 1000:1 to 1 :1 , preferably in the range of from 100:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 and particularly in the range of from 10:5 to 2:1 (compounds I : compound II).
  • any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the compounds I.
  • the compound l/compound II ratio is advantageously chosen so as to produce a synergistic effect.
  • the components can be used individually or already partially or completely mixed with one another to prepare the composition according to the invention. It is also possible for them to be packaged and used further as combination composition such as a kit of parts.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate (tank mix).
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate (tank mix).
  • composition according to the invention can be applied jointly (e.g. after tankmix) or consecutively.
  • compositions according to the invention can be shown by the examples described below which show the inventive merits of this invention, without being llimited thereto or thereby.
  • the active compounds are prepared as a stock solution comprising 25 mg of active compound which is made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol ® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99: 1.
  • the mixture is then made up to 100 ml with water.
  • This stock solution is diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.
  • the visually determined percentages of infected leaf areas are converted into efficacies in % of the untreated control.
  • the efficacy (E) is calculated as follows using Abbot's formula:
  • ⁇ corresponds to the fungicidal infection of the untreated (control) plants in %
  • An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • Sodium stearoyl lactylate was obtained from Dr. Straetmanns (Dermofeel ® SL).
  • the product orysastrobin was used as commercial finished formulation and diluted with water to the stated concentration of the active compound.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of the respective pathogen in the respective nutrient medium was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • MTP micro titer plate
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.
  • a spore suspension of Botrytis cinerea containing a aqueous biomalt medium was used.
  • a spore suspension of Pyricularia oryzae containing a aqueous biomalt medium was used.
  • a spore suspension of Septoria tritici containing a aqueous biomalt medium was used.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to mixtures comprising compounds I and compounds II as defined in the description and methods, use and compositions for combating phytopathogenic fungi in plants using these mixtures.

Description

Synergistic fungicidal mixtures comprising lactylates and method for combating phyto- pathogenic fungi
Description
The present invention relates to a mixture, comprising as active compounds
1 ) at least one compound of formula I
Figure imgf000002_0001
wherein
Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms, wherein the carbon chain is branched or unbranched,
X is H or CHs; n is an integer with a value of 1 to 10;
A is, if n > 1 , -CO-, or,
A is, if n = 1 , -CO- or a direct bond; or an agrochemically acceptable salt thereof,
and
2) at least one active compound II selected from groups A) to I): A) strobilurins
azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, me- tominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2-methyl-phen- oxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane-carboximidoyl- sulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2-chloro-5-[1 -(3- methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2-(3-(2,6-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- N-methyl-acetamide;
B) carboxamides
- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino- 4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3- trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;
- carboxylic morpholides: dimethomorph, flumorph, pyrimorph;
- benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide;
- other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
C) azoles
- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenocona- zole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquin- conazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4-chloro-phenyl)-2- ([1 ,2,4]triazol-1 -yl)-cycloheptanol;
- imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4-(3,4- dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;
D) heterocyclic compounds
- pyridines: fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3- yl]-pyridine, 2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro- pyridine-2,6-di-carbonitrile, N-(1 -(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloronicotinamide, N-[(5-bromo-3-chloro-pyridin-2-yl)-methyl]-2,4-dichloro- nicotinamide;
- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;
- piperazines: triforine;
- pyrroles: fenpiclonil, fludioxonil;
- morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
- piperidines: fenpropidin;
- dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
- non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro- pyrazole-1 -carbothioic acid S-allyl ester; - others: acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzo- quat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, pro- quinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3- propylchromen-4-one, 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H- benzoimidazole and 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6- trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine;
E) carbamates
- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulpho- carb, metiram, propineb, thiram, zineb, ziram;
- carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb,
propamocarb hydrochlorid, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
F) other active substances
- guanidines: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
- antibiotics: kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, polyoxine, validamycin A;
- nitrophenyl derivates: binapacryl, dinobuton, dinocap, nitrthal-isopropyl,
tecnazen,
organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
- sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;
- organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, ipro- benfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
- organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusul- famide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
- inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
- others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin,
metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxamine, tebufloquin, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3- difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(4-(4-fluoro- 3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N- methyl formamidine, N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine,
2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N- Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-
N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide;
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, flu- thiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohy- drojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
H) herbicides
- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, 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, thiobencarb, triallate;
- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxy- dim, tepraloxydim, tralkoxydim;
- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
- 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, dichlorprop, 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, flu- cetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodo- sulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, ox- asulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometu- ron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 -((2-chloro-6-propyl-imidazo[1 ,2-b]pyridazin-3- yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea;
- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, tri- aziflam;
- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron,
methabenzthiazuron,tebuthiuron;
- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyriben- zoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
- others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, ben- carbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopy- rone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentra- zone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosul- famide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pen- toxazone, pinoxaden, pyraclonil, pyraf I uf en-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro- 5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)- phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2- cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2- cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chloro- phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-
3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester;
I) insecticides
- organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyri- fos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofu- ran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme- thrin, 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: chlorflua- zuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spi- romesifen, spirotetramat;
- nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, 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, pyra- fluprole, 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, le- pimectin, spinosad, spinetoram;
- mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyri- daben, 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;
- sodium channel blockers: indoxacarb, metaflumizone;
- others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86), cyeno- pyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquinazon; in a synergistically effective amount. Therefore the present invention furthermore relates to a method for combating phy- topathogenic harmful fungi, which process comprises treating the fungi or the plants, the soil or seeds to be protected against fungal attack, with an effective amount of the mixtures as defined herein. The present invention also relates to an agrochemical composition which comprises a solvent or solid carrier and a mixture as defined herein.
Furthermore, the present invention also relates to seed coated with a mixture as defined herein or a composition thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
It is known to use fungicides to protect crop plants from phytopathogenic fungi. However, there is an increasing resistance against the use of fungicdes in food, aand nowadays many countries have legislation that prohibits or restricts the amount of active ingredient used for many fungicides in crop protection. Accordingly, there is a need for new active ingredients that have less toxic side effects and are known to be safe to human.
Another typical problem arising in the field of pathogen control lies in the need to reduce the dosage rates of the fungicides in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing pathogen control. A further problem encoutered concerns the need to have available fungal control agents which show an improved action against harmful fungi with a reduced amount of active compounds applied and/or a broadened spectrum of pathogens controlled.
Another difficulty in relation to the use of fungicides is that the repeated and exclusive application of an individual pesticidal compound or compounds of the same mode of action or chemical class leads in many cases to a rapid selection of fungal pathogens that have developed natural or adapted resistance against the active compound or chemical class in question.
Lactylates such as sodium stearoyl lactylate are well-known and safe cosmetic and food additives e.g. used as a dough strengthener in baked goods or as emulsifiers in cleansing products or as hair conditioner. It is noted that WO 2009/092787 describes an anti-bacterial animal feed composition comprising lactylates and/or glycolylates. An animal feed composition is described as being active against gram-positive bacteria in animals. The use for treating or preventing intestinal infections with Clostridium perfringens in animals is specified. While the anti-bacterial activity is elucidated, their efficacy against fungi and specifically against phytopathogenic fungi is not mentioned. There is nothing in this reference that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in
agrochemical compositions.
Likewise, US 2009/0082253 A1 relates to an antibacterial composition comprising lactylates and to its use as antibacterial agent active against gram-negative bacteria e.g. in the pharmaceutical field, in the feed industry and in the food and drink industry. The reduction or prevention of gram-negative human pathogenic bacteria such as Escherichia coli, Salmonella typhimurium and S. enteridis is specified. GB1 1 15480 suggests the use of acyated alpha-hydroxy carboxylic acids for food conservation and reduction of skin diseases. The compositions described for consumption by or application to humans or other animals have been shown to be active against human pathogenic bacteria and molds e.g. on packaged cheese or leather. There is nothing in these references that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in agrochemical compositions.
Further, WO 2006/006788 describes a fungicidally active composition of anhydrous milk fat as fungicidally active component and an emulsifier and an antioxidant such as . In one example, calcium stearoyi lactylate is used as an emulsifier for the milk fat and a mixture of propyl gallate and citric acid monoglyceride ester as an antioxidant.
Thus, lactylates, are however, not known to be effective against phytopathogenic fungi or to form synergistically effective mixtures for the control of phytopathogenic fungi. They are therefore also not used as fungicidal agents in agrochemical compositions. In fact, their regulatory status is that of of them being used as
emulsifying agents only.
Agriculturally useful salts of the compounds I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammo- nium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfo- nium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
The term "an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms" refers to a univalent acyl radical [RCO] from a Ci-C34-alkyl carboxylic acid or from a Ci-C34-alkenyl carboxylic acid with a straight-chained or branched saturated or unsaturated (having at least one double bond) hydrocarbon group, for example bu- tanoyl, butenoyl, hexanoyl (caproyl) (Ce), octoyl (capryloyl) (Cs), lauroyl (C12), myristoyl (C14), hexadecanoyl (palmitoyl) (C16), stearoyi (ds), oleoyl (C18, C18: 1 ), linoleoyl (Cis, C1 8:2), linolenoyl (Cie, C18:3) and erucoyl (C22, C22: 1 ).
According to one embodiment of the invention, preference is given to lactylates or glycolylates of formula I (compounds I) wherein A is -CO-. According to another embodiment, preference is given to lactylates or lactate esters of formula I wherein X is CH3, more preferably to lactylates of formula I, wherein A is -CO- and X is CH3. According to a further embodiment, the use of glycolylates of formula I, wherein A is -CO- and X is H is preferred.
In another embodiment, Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-20 carbon atoms. More in particular, Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-1 8 carbon atoms. In this embodiment, suitable substituents include acyl groups having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 1 0 carbon atoms (decanoyl), 12 carbon atoms (lauroyl), 14 carbon atoms (myristoyl), 1 6 carbon atoms (palmitoyl), 18 carbon atoms (stearoyi). Mixtures of two or more com- pounds may also be used. More preferred substituents Ac are selected from acyl radicals of an alkyl or alkenyl carboxylic acid having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 10 carbon atoms (decanoyl), 12 carbon atoms (lauroyl) and 14 carbon atoms (myristoyi).
Where a salt of compounds of formula I is used, the use of a Na, K, Ca, Mg, Fe(ll), Zn, NH4, or Cu(ll) salt may be preferred with a Na, K, Ca, or Mg salt being particularly preferred.
The value for n is preferably in the range of 1 -5. More preferably, n has a value of 1 , 2, or 3, in particular n is 2.
The use of lauroyl lactylate, myristoyi lactylate, and their sodium salts is particularly preferred. In one embodiment, a mixture is used comprising 5-95 wt.% of lauroyl lactylate and 95-5 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds are used, more in particular, a mixture is used comprising 25-75 wt. %, more in particular 40-60 wt. % of lauroyl lactylate, and 75-25 wt.%, more in particular 40-60 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds.
Moreover, we have found that simultaneous, that is joint or separate, application of compound I and at least one compound II or successive application of a compound I and of a compound II allows better control of harmful fungi than is possible with the individual compounds alone (synergistic mixtures). Furthermore, synergistic effects in relation with the insecticidal and/or herbicidal action has been found with the inventive mixtures.
The compounds II, their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available and known, for example, from the references below:
benalaxyl, methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate (DE 29 03 612);
metalaxyl, methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (GB 15 00 581 );
ofurace, (RS)-a -(2-chloro-N-2,6-xylylacetamido)-Y -butyrolactone [CAS RN 58810-48- 3]; oxadixyl; N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide (GB 20 58 059); aldimorph, "4-alkyl-2,5(or 2,6)-dimethylmorpholine", comprising 65-75% of 2,6-dimethylmorpholine and 25-35% of 2,5-dimethylmorpholine, comprising more than 85% of 4-dodecyl-2,5(or 2,6)-dimethylmorpholine, where " a l kyl " also includes octyl, decyl, tetradecyl and hexadecyl, with a cis/trans ratio of 1 :1 [CAS RN 91315-15-0]; dodine, 1 -dodecylguanidinium acetate (Plant Dis. Rep., Vol. 41 , p.1029 (1957)); dode- morph, 4-cyclododecyl-2,6-dimethylmorpholine (DE 1 198125); fenpropimorph, (RS)- cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (DE 27 52 096); fenpropidin, (RS)-1 -[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine (DE 27 52 096); guazatine, mixture of the reaction products from the amidation of technical grade imi- nodi(octamethylene)diamine, comprising various guanidines and polyamines [CAS RN 108173-90-6]; iminoctadine, 1 ,1 '-iminodi(octamethylene)diguanidine (Congr. Plant Pathol., 1 ., p.27 (1968); spiroxamine, (8-tert-butyl-1 ,4-dioxaspiro[4.5]dec-2-yl)diethyl- amine (EP-A 281 842); tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE 1 1 64 152); pyrimethanil, 4,6-dimethylpyrimidin-2-ylphenylamine (DD-A 151 404); mepanipyrim, (4- methyl-6-prop-1 -ynylpyrimidin-2-yl)phenylamine (EP-A 224 339); cyprodinil, (4-cyclo- propyl-6-methylpyrimidin-2-yl)phenylamine (EP-A 310 550); cycloheximid, 4-{(2R)-2- [(1 S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione [CAS RN 66-81 -9]; griseofulvin, 7-chloro-2\4,6-trimethoxy-6'-methylspiro[benzofuran- 2(3H),1 '-cyclohex-2'-ene]-3,4'-dione [CAS RN 126-07-8]; kasugamycin, 3-0-[2-amino- 4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-a -D-arabino-hexopyranosyl]-D- chiro-inositol [CAS RN 6980-18-3]; natamycin, (8E,14E,16E,18E,20E)-(1 R,3S,5R, 7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-3 -D-mannopyranosyloxy)- 1 ,3,26-trihydroxy-12-methyl-10-oxo-6,1 1 ,28-trioxatricyclo[22.3.1.05'7]octacosa- 8,14,16,18,20-pentaene-25-carboxylic acid [CAS RN 7681 -93-8]; polyoxin, 5-(2-amino- 5-0-carbamoyl-2-deoxy-L-xylonamido)-1 -(5-carboxy-1 ,2,3,4-tetrahydro-2,4-dioxo- pyrimidin-1 -yl)-1 ,5-dideoxy-3 -D-allofuranuronic acid [CAS RN 22976-86-9]; streptomycin, 1 ,1 ' -{1 -L-(1 ,3,5/2,4,6)-4-[5-deoxy-2-0-(2-deoxy-2-methylamino-a -L-gluco- pyranosyl)-3-C-formyl-a -L-lyxofuranosyloxy]-2,5,6-trihydroxycyclohex-1 ,3-ylene}di- guanidine (J. Am. Chem. Soc. Vol. 69, p.1234 (1947)); bitertanol, β -([1 ,1 ' -biphenyl]- 4-yloxy)-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1-ethanol (DE 23 24 020); bromu- conazole, 1 -[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1 H-1 ,2,4- triazole (Proc. 1990 Br. Crop. Prot. Conf. - Pests Dis. Vol. 1 , p. 459); cyproconazole, 2-(4-chlorophenyl)-3-cyclopropyl-1 -[1 ,2,4]triazol-1 -ylbutan-2-ol (US 4 664 696); difeno- conazole, 1 -{2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-[1 ,3]dioxolan-2-ylmeth- yl}-1 H-[1 ,2,4]triazole (GB-A 2 098 607); diniconazole, (β Ε)-β -[(2,4-dichlorophenyl)- methylene]-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1 -ethanol (Noyaku Kagaku, 1983, Vol. 8, p. 575); enilconazole (imazalil), 1 -[2-(2,4-dichlorphenyl)-2-(2-propenyloxy)ethyl]- 1 H-imidazole (Fruits, 1973, Vol. 28, p. 545); epoxiconazole, (2RS,3SR)-1 -[3-(2-chloro- phenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1 H-1 ,2,4-triazole (EP-A 196 038); fenbu- conazole, a -[2-(4-chlorophenyl)ethyl]-a -phenyl-1 H-1 ,2,4-triazole-1 -propanenitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis. Vol. 1 , p. 33); fluquinconazole, 3-(2,4- dichlorophenyl)-6-fluoro-2-[1 ,2,4]- triazol-1 -yl-3H-quinazolin-4-one (Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 41 1 (1992)); flusilazole, 1 -{[bis-(4-fluorophenyl)methyl- silanyl]methyl}-1 H-[1 ,2,4]triazole (Proc. Br. Crop Prot. Conf.-Pests Dis., 1 , 413 (1984)); flutriafol, a -(2-fluorophenyl)-a -(4-fluorophenyl)-1 H-1 ,2,4-triazole-1 -ethanol (EP 15 756); hexaconazole, 2-(2,4-dichlorophenyl)-1 -[1 ,2,4]triazol-1 -ylhexan-2-ol (CAS RN 79983-71 -4); ipconazole, 2-[(4-chlorophenyl)methyl]-5-(1 -methylethyl)-1 -(1 H-1 ,2,4- triazol-1 -ylmethyl)cyclopentanol (EP 267 778), metconazole, 5-(4-chlorobenzyl)-2,2- dimethyl-1 -[1 ,2,4]triazol-1 -ylmethylcyclopentanol (GB 857 383); myclobutanil, 2-(4- chlorophenyl)-2-[1 ,2,4]triazol-1 -ylmethylpentanenitrile (CAS RN 88671- 89- 0); pen- conazole, 1 -[2-(2,4-dichlorophenyl)pentyl]-1 H-[1 ,2,4]triazole (Pesticide Manual, 12th Ed. (2000), S.712); propiconazole, 1 -[[2-(2,4-dichlorophenyl)-4-propyl-1 ,3-dioxolan-2- yl]methyl]-1 H-1 ,2,4-triazole (BE 835 579); prochloraz, N-(propyl-[2-(2,4,6-trichloro- phenoxy)ethyl])imidazole-1 -carboxamide (US 3 991 071 ); prothioconazole, 2-[2-(1 - chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1 ,2,4]triazole-3- thione (WO 96/16048); simeconazole, a -(4-fluorophenyl)-a -[(trimethylsilyl)methyl]-1 H- 1 ,2,4-triazole-1 -ethanol [CAS RN 149508-90-7], tebuconazole, 1 -(4-chlorophenyl)-4,4- dimethyl-3-[1 ,2,4]triazol-1 -ylmethylpentan-3-ol (EP-A 40 345); tetraconazole, 1 -[2-(2,4- dichlorophenyl)-3-(1 ,1 ,2,2-tetrafluoroethoxy)propyl]-1 H-1 ,2,4-triazole (EP 234 242); triadimefon, 1 -(4-chlorophenoxy)-3,3-dimethyl-1 -(1 H-1 ,2,4-triazol-1 -yl)-2-butanone (BE 793 867); triadimenol, β -(4-chlorophenoxy)-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1 - ethanol (DE 23 24 010); triflumizol, (4-chloro-2-trifluormethylphenyl)-(2-propoxy-1 - [1 ,2,4]triazol-1 -ylethyliden)-amine (JP-A 79/1 19 462); triticonazole, (5E)-5-[(4- chlorophenyl)methylene]-2,2-dimethyl-1 -(1 H-1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (FR 26 41 277); iprodione, N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1 - carboxamide (GB 13 12 536); myclozolin, (RS)-3-(3,5-dichlorophenyl)-5-methoxy- methyl-5-methyl-1 ,3-oxazolidine-2,4-dione [CAS RN 54864-61 -8]; procymidone, N-(3,5- dichlorophenyl)-1 ,2-dimethylcyclopropane-1 ,2-dicarboximide (US 3 903 090); vinclo- zolin, 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (DE-A 22 07 576); ferbam, iron(3+) dimethyldithiocarbamate (US 1 972 961 ); nabam, disodium ethylene- bis(dithiocarbamate) (US 2 317 765); maneb, manganese ethylenebis(dithiocarbamate) (US 2 504 404); mancozeb, manganese ethylenebis(dithiocarbamate) polymer com- plex zinc salt (GB 996 264); metam, methyldithiocarbaminic acid (US 2 791 605); meti- ram, zinc ammoniate ethylenebis(dithiocarbamate) (US 3 248 400); propineb, zinc pro- pylenebis(dithiocarbamate) polymer (BE 61 1 960); polycarbamate, bis(dimethylcar- bamodithioato-K S,K S' )[μ -[[1 ,2-ethanediylbis[carbamodithioato-K S,K S' ]](2- )]]- di[zinc] [CAS RN 64440-88-6]; thiram, bis(dimethylthiocarbamoyl) disulfide (DE 642 532); ziram, dimethyldithiocarbamate [CAS RN 137-30-4]; zineb, zinc ethylene- bis(dithiocarbamate) (US 2 457 674); anilazine, 4,6-dichloro-N-(2-chlorophenyl)-1 ,3,5- triazine-2-amine (US 2 720 480); benomyl, N-butyl-2-acetylaminobenzoimidazole-1 - carboxamide (US 3 631 176); boscalid, 2-chloro-N-(4' -chlorobiphenyl-2-yl)nicotin- amide (EP-A 545 099); carbendazim, methyl (1 H-benzoimidazol-2-yl)carbamate (US 3 657 443); carboxin, 5,6-dihydro-2-methyl-N-phenyl-1 ,4-oxathiin-3-carboxamide (US 3 249 499); oxycarboxin, 5,6-dihydro-2-methyl-1 ,4-oxathiin-3-carboxanilide 4,4-dioxide (US 3 399 214); cyazofamid, 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1 H- imidazole-1 -sulfonamide (CAS RN 1201 16-88-3]; dazomet, 3,5-dimethyl-1 ,3,5-thia- diazinane-2-thione (Bull. Soc. Chim. Fr. Vol. 15, p. 891 (1897)); dithianon, 5,10-dioxo- 5,10-dihydronaphtho[2,3-b][1 ,4]dithiin-2,3-dicarbonitrile (GB 857 383); famoxadone, (RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1 ,3-oxazolidine-2,4-dione [CAS RN 131807-57-3]; fenamidone, (S)-1 -anilino-4-methyl-2-methylthio-4-phenylimidazolin-5- one [CAS RN 161326-34-7]; fenarimol, a -(2-chlorophenyl)-a -(4-chlorophenyl)-5- pyrimidinemethanol (GB 12 18 623); fuberidazole, 2-(2-furanyl)-1 H-benzimidazole (DE 12 09 799); flutolanil, a ,a ,a -trifluoro-3' -isopropoxy-o-toluanilide (JP 1 104514); furametpyr, 5-chloro-N-(1 ,3-dihydro-1 ,1 ,3-trimethyl-4-isobenzofuranyl)-1 ,3-dimethyl-1 H- pyrazole-4-carboxamide [CAS RN 123572-88-3]; isoprothiolane, diisopropyl 1 ,3-dithio- lan-2-ylidenemalonate (Proc. Insectic. Fungic. Conf. 8. Vol. 2, p. 715 (1975)); mepronil, 3 '-isopropoxy-o-toluanilide (US 3 937 840); nuarimol, a -(2-chlorophenyl)-a -(4-fluoro- phenyl)-5-pyrimidinemethanol (GB 12 18 623); fluopicolide (picobenzamid), 2,6-di- chloro-N-(3-chloro-5-trifluoromethylpyridin-2-ylmethyl)benzamide (WO 99/42447); pro- benazole, 3-allyloxy-1 ,2-benzothiazole 1 ,1 -dioxide (Agric. Biol. Chem. Vol. 37, p. 737 (1973)); proquinazid, 6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one (WO 97/48684); pyrifenox, 2' ,4' -dichloro-2-(3-pyridyl)acetophenone (EZ)-O-methyloxime (EP 49 854); pyroquilon, 1 ,2,5,6-tetrahydropyrrolo[3,2,1 -ij]quinolin-4-one (GB 139 43 373); quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline (US 5 240 940); silthiofam, N- allyl-4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide [CAS RN 175217-20-6]; thiabendazole, 2-(1 ,3-thiazol-4-yl)benzimidazole (US 3 017 415); thifluzamide, 2' ,6' - dibromo-2-methyl-4' -trifluormethoxy-4-trifluormethyl-1 ,3-thiazole-5-carboxanilide
[CAS RN 130000-40-7]; thiophanate-methyl, 1 ,2-phenylenebis(iminocarbonothioyl)- bis(dimethylcarbamate) (DE-A 19 30 540); tiadinil, 3' -chloro-4,4' -dimethyl-1 ,2,3- thiadiazole-5-carboxanilide [CAS RN 223580-51 -6]; tricyclazole, 5-methyl-1 ,2,4- triazolo[3,4-b][1 ,3]benzothiazole [CAS RN 41814-78-2]; triforine, Ν,Ν' -{piperazine- 1 ,4-diylbis[(trichlormethyl)methylene]}diformamide (DE 19 01 421 ); Bordeaux mixture, mixture of CuS04 x 3Cu(OH)2 x 3CaS04 [CAS RN 801 1 -63-0] copper acetate,
Cu(OCOCH3)2 [CAS RN 801 1 -63-0]; copper oxychloride, Cu2CI(OH)3 [CAS RN 1332- 40-7]; basic copper sulfate, CuS04 [CAS RN 1344-73-6]; binapacryl, (RS)-2-sec-butyl- 4,6-dinitrophenyl 3-methylcrotonate [CAS RN 485-31 -4]; dinocap, the mixture of 2,6- dinitro-4-octylphenylcrotonate and 2,4-dinitro-6-octylphenylcrotonate, where " octyl" is a mixture of 1 -methylheptyl, 1 -ethylhexyl and 1 -propylpentyl (US 2 526 660); dinobu- ton, (RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21 -7]; ni- trothal-isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic. Fungic. Conf. 7., Vol. 2, p. 673 (1973)); fenpiclonil, Fludioxonil, 4-(2,3-dichlorophenyl)-1 H-pyrrole-3- carbonitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., Vol. 1 , p. 65); fludioxonil, 4- (2,2-difluorobenzo[1 ,3]dioxol-4-yl)-1 H-pyrrole-3-carbonitrile (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. (1995), p. 482); acibenzolar-S- methyl, methyl 1 ,2,3-benzothiadiazol-7-carbothioate [CAS RN 135158-54-2]; fluben- thiavalicarb (benthiavalicarb), isopropyl {(S)-1 -[(1 R)-1 -(6-fluorobenzothiazol-2-yl)- ethylcarbamoyl]-2-methylpropyl}carbamate (JP-A 09/323 984); carpropamid, 2,2-di- chloro-N-[1 -(4-chlorphenyl)ethyl]-1 -ethyl-3-methylcyclopropanecarboxamide [CAS RN 104030-54-8]; chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3 290 353); cy- flufenamid, (Z)-N-[a -(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]- 2-phenylacetamide (WO 96/19442); cymoxanil, 1 -(2-cyano-2-methoxyiminoacetyl)-3- ethylurea (US 3 957 847); diclomezine, 6-(3,5-dichlorophenyl-p-tolyl)pyridazin-3(2H)- one (US 4 052 395); diclocymet, (RS)-2-cyano-N-[(R)-1 -(2,4-dichlorophenyl)ethyl]-3,3- dimethylbutyramide [CAS RN 139920-32-4]; diethofencarb, isopropyl 3,4-diethoxy- carbanilate (EP 78 663); edifenphos, O-ethyl S,S-diphenyl phosphorodithioate (DE 14 93 736); ethaboxam, N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazole- carboxamide (EP-A 639 574); fenhexamid, N-(2,3-dichloro-4-hydroxyphenyl)-1 - methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, Vol. 2, p. 327); fentin acetate, triphenyltin (US 3 499 086); fenoxanil, N-(1 -cyano-1 ,2- dimethylpropyl)-2-(2,4-dichlorophenoxy)propanamide (EP 262 393); ferimzone, me- panipyrim, (Ζ)-2' -methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7]; fluazinam, 3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5- (trifluoromethyl)-2-pyridinamine (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. (1995), p. 474); fosetyl, fosetyl-aluminum, ethylphosphonate (FR 22 54 276); iprovalicarb, isopropyl [(1 S)-2-methyl-1 -(1 -p-tolylethylcarbamoyl)propyl]- carbamate (EP-A 472 996); hexachlorbenzene (C. R. Seances Acad. Agric. Fr., Vol. 31 , p. 24 (1945); metrafenon, 3' -bromo-2,3,4,6' -tetramethoxy-2' ,6-dimethylbenzo- phenone (US5,945,567); pencycuron, 1 -(4-chlorobenzyl)-1 -cyclopentyl-3-phenylurea (DE 27 32 257); penthiopyrad, (RS)-N-[2-(1 ,3-dimethylbutyl)-3-thienyl]-1 -methyl-3- (trifluoromethyl)-l H-pyrazole-4-carboxamide (JP 10130268); propamocarb, propyl 3- (dimethylamino)propylcarbamate (DE 15 67 169); phthalide (DE 16 43 347); toloclofos- methyl, 0-2,6-dichloro-p-tolyl 0,0-dimethyl phosphorothioate (GB 14 67 561 ); quintoz- ene, pentachlornitrobenzene (DE 682 048); zoxamide, (RS)-3,5-dichloro-N-(3-chloro-1 - ethyl-1 -methyl-2-oxopropyl)-p-toluamide [CAS RN 156052-68-5]; azoxystrobin, methyl 2-{2-[6-(2-cyano-1 -vinyl penta-1 , 3-dienyloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy- acrylate (EP 382 375); dimoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-[a -(2,5- xylyloxy)-o-tolyl]acetamide (EP 477 631 ); enestroburin, methyl 2-{2-[3-(4-chlorophenyl)- 1 -methylallylideneaminooxymethyl]phenyl}-3-methoxyacrylate (EP 936 213); fluox- astrobin, (E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro- 1 ,4,2-dioxazin-3-yl)methanone O-methyloxime (WO 97/27189); kresoxim-methyl, methyl (E)-methoxyimino[a -(o-tolyloxy)-o-tolyl]acetate (EP 253 213); metominostrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide (EP 398 692); orysas- trobin, (2E)-2-(methoxyimino)-2-{2-[(3E,5E,6E)-5-(methoxyimino)-4,6-dimethyl-2,8-di- oxa-3,7-diazanona-3,6-dien-1 -yl]phenyl}-N-methylacetamide (WO 97/15552); picoxy- strobin, methyl 3-methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]acrylate (EP 278 595); pyraclostrobin, methyl N-{2-[1 -(4-chlorophenyl)-1 H-pyrazol-3-yloxymeth- yl]phenyl}(N-methoxy)carbamate (WO 96/01256); trifloxystrobin, methyl (E)-methoxy- imino-{(E)-a -[1 -(a ,a ,a -trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetate (EP 460 575); captafol, N-(1 ,1 ,2,2-tetrachloroethylthio)cyclohex-4-ene-1 ,2-dicarboximide (Phytopathology, Vol. 52, p. 754 (1962)); captan, N-(trichloromethylthio)cyclohex-4-ene-1 ,2- dicarboximide (US 2 553 770); dichlofluanid, N-dichlorofluoromethylthio-N,N-dimethyl- N-phenylsulfamide (DE 1 1 93 498); folpet, N-(trichlormethylthio)phthalimide (US 2 553 770); tolylfluanid, N-dichlorofluoromethylthio-N,N-dimethyl-N-p-tolylsulfamide (DE 1 1 93 498); dimethomorph, 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1 -morpholin-4- yl-propenone (EP 120 321 ); flumetover, 2-(3,4-dimethoxyphenyl)-N-ethyl-a ,a ,a -tri- fluoro-N-methyl-p-toluamide [AGROW no. 243, 22 (1995)]; flumorph, 3-(4-fluorophen- yl)-3-(3,4-dimethoxyphenyl)-1 -morpholin-4-ylpropenone (EP 860 438); 5-Amino-2- isopropyl-3-oxo-4-o-tolyl-2,3-dihydro-pyrazole-1 -carbothioic acid S-allyl ester
(CN1939128).
The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP- A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783;
WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358;
WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ;
WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690;
WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325;
WO 06/87343; WO 07/82098; WO 07/90624).
According to the present invention, it may be preferred that the mixtures comprise as compound II a compound that is selected from the group A), C), D), E), F) and G).
According to another embodiment of the invention, mixtures comprise as compound II a compound that is selected from the group H).
According to a further embodiment, mixtures comprise as compound II a compound that is selected from the group I).
According to a further embodiment, mixtures comprise as compound II a compound of group A (strobilurins), preferably selected from pyraclostrobin, kresoxim-methyl, azoxystrobin, fluoxastrobin, trifloxystrobin, enestroburin and pyribencarb, more preferably from pyraclostrobin and fluoxastrobin.
According to a further emobodiment, group B) of compounds II is as follows:
- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, sedaxane, carboxin, penthiopyrad, boscalid, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isoti- anil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, , tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 , 1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3- difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl- 2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl- butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;
- carboxylic morpholides: dimethomorph, flumorph;
- benzoic acid amides: flumetover, fluopicolde, fluopyram, zoxamide, N-(3-ethyl- 3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide;
- other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
According to a further embodiment, mixtures comprise as compound II a compound of group B (carboxamides), preferably selected from bixafen, penthiopyrad, sedaxane, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl- 1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl- 5-fluoro-1 H-pyrazole-4-carboxamide, fluopyram, mandiproamid, amisulbrom, flutolanil, metalaxyl, oxadixyl, benalaxyl, ofurace, dimethomorph, zoxamide and flumetover.
According to a further embodiment, mixtures comprise as compound II a compound of group C (azoles), preferably selected from epoxiconazole, prochloraz, ethaboxam, benomyl, carbendazim, thiabendazole, difenoconazole, flusilazole, tebuconazol, cypro- conazole, prothioconazole and 1 -(4-chloro-phenyl)-2-([1 ,2,4]triazol-1 -yl)-cycloheptanol, more preferably selected from epoxiconazole and prothioconazole.
According to a further embodiment, mixtures comprise as compound II a compound of group D (heterocyclic compounds), preferably selected from famoxadone, fenami- done, folpet, captan and 5-amino-2-isopropyl-3-oxo-4-o-tolyl-2,3-dihydro-pyrazole- 1 -carbothioic acid S-allyl ester.
According to a further embodiment, the mixtures comprise at least one compound (II) selected from the group of E) carbamates, more preferably selected from man- cozeb, maneb and metiram.
According to a further embodiment, mixtures comprise as compound II a compound of group F (other active substances), preferably selected from cymoxanil, thiophanate- methyl, fosetyl, chlorothalonil, copper, copper hydroxide and copper oxychloride.
Preference is also given to three-component mixtures of one compound I with two of the active compounds II mentioned above.
The mixtures and compositions according to the invention are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The mixtures and compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably the inventive mixtures and compositions are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This in- eludes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with the inventive combination of compounds I and compounds II and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
The agrochemical compositions and the fungicidal mixtures, respectively, are particularly suitable for controlling the following fungal plant diseases:
Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Bipolaris and Drechslera spp.
(teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice
(e. g. G. fujikuroi: Bakanae disease); Guignardia bidwellii (black rot) on vines; Microdo- chium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Moni- linia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. para- sitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P.
manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight); Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, and asparagus (e. g. P. asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricu- laria spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhynchosporium secalis (scald) on barley, rye and triticale; Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears.
In particular, the mixtures and the compositions thereof are effective against plant pathogens in speciality crops such as vine, fruits, hop, vegetables and tabacco - see the above list.
Plant propagation materials may be treated with the mixtures and compositions of the invention prophylactically either at or before planting or transplanting.
The present invention also relates to a pesticidal agent comprising at least one solid or liquid carrier and a composition as described herein.
The compounds I and compounds II, and salts thereof can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The composition type depends on the particular intended purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention.
Examples for composition types are suspensions (SC, OD, FS), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF). Usually the composition types (e. g. SC, OD, FS, WG, SG, WP, SP, SS, WS, GF) are employed diluted. Composition types such as DP, DS, GR, FG, GG and MG are usually used undiluted.
The compositions are prepared in a known manner (cf. 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, S. 8-57 und ff. WO 91/13546, US 4,172,714,
US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030,
GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (J. Wiley & Sons, New York, 1961 ), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001 ).
The agrochemical compositions may also comprise auxiliaries which are customary in agrochemical compositions. The auxiliaries used depend on the particular applica- tion form and active substance, respectively.
Examples for suitable auxiliaries are solvents, solid carriers, dispersants or emulsifi- ers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and anorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment for- mulations).
Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their de- rivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone and gamma-butyrolactone, fatty acid dimethyla- mides, fatty acids and fatty acid esters and strongly polar solvents, e. g. amines such as N-methylpyrrolidone.
Solid carriers are mineral earths such as silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
Suitable surfactants (adjuvants, wtters, tackifiers, dispersants or emulsifiers) are alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, such as ligninsoulfonic acid (Borresperse® types, Borregard, Norway) phenolsulfonic acid, naphthalenesulfonic acid (Morwet® types, Akzo Nobel, U.S.A.), dibutylnaphthalene- sulfonic acid (Nekal® types, BASF, Germany), and fatty acids, alkylsulfonates, alkyl- arylsulfonates, alkyl sulfates, laurylether sulfates, fatty alcohol sulfates, and sulfated hexa-, hepta- and octadecanolates, sulfated fatty alcohol glycol ethers, furthermore condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy-ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearyl- phenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and proteins, denatured proteins, polysaccharides (e. g. methylcellulose), hydrophobically modified starches, polyvinyl alcohols (Mowiol® types, Clariant, Switzerland), polycarboxylates (Sokolan® types, BASF, Germany), polyalkoxylates, polyvinyl- amines (Lupasol® types, BASF, Germany), polyvinylpyrrolidone and the copolymers therof.
Examples for thickeners (i. e. compounds that impart a modified flowability to compositions, i. e. high viscosity under static conditions and low viscosity during agitation) are polysaccharides and organic and anorganic clays such as Xanthan gum (Kelzan®, CP Kelco, U.S.A.), Rhodopol® 23 (Rhodia, France), Veegum® (R.T. Vanderbilt, U.S.A.) or Attaclay® (Engelhard Corp., NJ, USA).
Bactericides may be added for preservation and stabilization of the composition. Examples for suitable bactericides are those based on dichlorophene and benzyl- alcohol hemi formal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide® MBS from Thor Chemie).
Examples for suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Examples for anti-foaming agents are silicone emulsions (such as e. g. Silikon® SRE, Wacker, Germany or Rhodorsil®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, fluoroorganic compounds and mixtures thereof.
Suitable colorants are pigments of low water solubility and water-soluble dyes. Examples to be mentioned und the designations rhodamin B, C. I. pigment red 1 12, C. I. solvent red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples for tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols and cellulose ethers (Tylose®, Shin-Etsu, Japan).
Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the compounds I and compounds II with at least one solid carrier.
Granules, e. g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active substances to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of ac- tive substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Water-soluble concentrates (LS), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are usu- ally employed for the purposes of treatment of plant propagation materials, particularly seeds. These compositions can be applied to plant propagation materials, particularly seeds, diluted or undiluted. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before sowing. Methods for applying or treating agrochemical compounds and compositions thereof, respectively, on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting, dusting and soaking application methods of the propagation material. In a preferred embodiment, the compounds or the compositions thereof, respectively, are applied on to the plant propagation mate- rial by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
In a preferred embodiment, a suspension-type (FS) composition is used for seed treatment. Typcially, a FS composition may comprise 1 -800 g/l of active substance, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
The active substances can be used as such or in the form of their compositions, e. g. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading, brushing, immersing or pouring. The application forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active substances according to the invention.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active substance concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.001 to 1 % by weight of active substance.
The active substances may also be used successfully in the ultra-low-volume proc- ess (ULV), it being possible to apply compositions comprising over 95% by weight of active substance, or even to apply the active substance without additives.
When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active substance per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 1 to 1000 g, preferably from 5 to 100 g, per 100 kilogram of seed are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, e. g., 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the mixtures or the compositions comprising them, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
Adjuvants which can be used are in particular organic modified polysiloxanes such as Break Thru S 240®; alcohol alkoxylates such as Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers, e. g. Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates such as Lutensol XP 80®; and dioctyl sulfo- succinate sodium such as Leophen RA®.
The compositions 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 immeadiately prior to use (tank mix).
According to this invention, applying compounds I together with a compound II is to be understood to denote, that compounds I and at least one compound II occur simultaneously at the site of action (i.e. the harmful fungi to be controlled or their habitats such as infected plants, plant propagation materials, particularly seeds, surfaces, mate- rials or the soil as well as plants, plant propagation materials, particularly seeds, soil, surfaces, materials or rooms to be protected from fungal attack) in an effective amount. This can be obtained by applying compounds I and compound II simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
In the mixtures and compositions according to the invention the weight ratio of compounds I and compound II generally depends from the properties of the active sub- stances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and particularly in the range of from 1 :5 to 5:1 (compounds I : compound II). In another embodiment, the weight ratio of compounds I and compound II is in the range of from 1000:1 to 1 :1 , preferably in the range of from 100:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 and particularly in the range of from 10:5 to 2:1 (compounds I : compound II).
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the compounds I.
In the mixtures and compositions, the compound l/compound II ratio is advantageously chosen so as to produce a synergistic effect.
The term "synergstic effect" is understood to refer in particular to that defined by Colby's formula (Colby, S. R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp. 20-22, 1967).
The term "synergistic effect" is also understood to refer to that defined by application of the Tammes method, (Tammes, P. M. L, "Isoboles, a graphic representation of synergism in pesticides", Netherl. J. Plant Pathol. 70, 1964).
The components can be used individually or already partially or completely mixed with one another to prepare the composition according to the invention. It is also possible for them to be packaged and used further as combination composition such as a kit of parts.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate (tank mix).
In a further embodiment, either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate (tank mix).
In a further embodiment, either individual components of the composition according to the invention or partially premixed components can be applied jointly (e.g. after tankmix) or consecutively.
The fungicidal action of the compositions according to the invention can be shown by the examples described below which show the inventive merits of this invention, without being llimited thereto or thereby.
Glass house Trials
The active compounds, separately or jointly, are prepared as a stock solution comprising 25 mg of active compound which is made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99: 1. The mixture is then made up to 100 ml with water.
This stock solution is diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.
The visually determined percentages of infected leaf areas are converted into efficacies in % of the untreated control.
The efficacy (E) is calculated as follows using Abbot's formula:
E = (1 - α/β ) ■ 100 a corresponds to the fungicidal infection of the treated plants in % and
β corresponds to the fungicidal infection of the untreated (control) plants in % An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficacies of active compound combinations were determined using Colby's formula (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1 5, pp. 20-22, 1967) and compared with the observed efficacies.
Colby's formula: E = x + y - χ · y/100
E expected efficacy, expressed in % of the untreated control, when using the
mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active
compound A at the concentration a
y efficacy, expressed in % of the untreated control, when using the active
compound B at the concentration b.
Microstests
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. Sodium stearoyl lactylate was obtained from Dr. Straetmanns (Dermofeel® SL).
The product orysastrobin was used as commercial finished formulation and diluted with water to the stated concentration of the active compound.
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of the respective pathogen in the respective nutrient medium was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
The measured parameters were compared to the growth of the active compound- free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.
The expected efficacies of active compound mixtures were determined using Colby's formula [R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficacies. Use example 1. Activity against the grey mold pathogen Botrytis cinerea
A spore suspension of Botrytis cinerea containing a aqueous biomalt medium was used.
Figure imgf000025_0001
Use example 2. Activity against the rice blast pathogen Pyricularia oryzae
A spore suspension of Pyricularia oryzae containing a aqueous biomalt medium was used.
Active compound / Concentration Mixture Observed Calculated efficacy active mixture (ppm) efficacy according to Colby
(%)
Sodium stearoyl
4
lactylate 2
Fluoxastrobin 0.016 - 12
Mancozeb 1 - 18
Sodium stearoyl
4
lactylate + 250 : 1 39 14
Fluoxastrobin 0.016
Sodium stearoyl
4
lactylate + 4 : 1 45 19
Mancozeb 1
Use example 3. Activity against the wheat leaf blotch pathogen Septoria tritici
A spore suspension of Septoria tritici containing a aqueous biomalt medium was used.
Active compound / Concentration Mixture Observed Calculated efficacy active mixture (ppm) efficacy according to Colby
(%)
Sodium stearoyl 16 - 15
lactylate 4 13
Fluoxastrobin 0.063 - 18
Prothioconazole 0.063 - 19
Sodium stearoyl
16
lactylate + 250 : 1 94 30 Fluoxastrobin 0.063
Sodium stearoyl
4
lactylate + 4 : 1 59 30 Prothioconazole 0.063

Claims

Claims
1 . A mixture, comprising as active compounds
1 ) at least one compound of formula I
Figure imgf000027_0001
wherein
Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms, wherein the carbon chain is branched or unbranched,
X is H or CHs; n is an integer with a value of 1 to 10;
A is, if n > 1 , -CO-, or
A is, if n = 1 , -CO- or a direct bond; or an agrochemically acceptable salt thereof; and
2) at least one active compound II selected from groups A) to I): A) strobilurins
azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrame- tostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2- methyl-phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N- methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2- chloro-5-[1 -(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2-(3- (2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2- methoxyimino-N-methyl-acetamide;
B) carboxamides
- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, car- boxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thif- luzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro- N-(1 ,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(3',4',5'-trifluorobiphenyl- 2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-trifluoro- methylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carbox- amide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide;
- carboxylic morpholides: dimethomorph, flumorph, pyrimorph;
- benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide; - other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracy- clin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
C) azoles
- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difeno- conazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ip- conazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, pen- conazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4- chloro-phenyl)-2-([1 ,2,4]triazol-1 -yl)-cycloheptanol;
- imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4- (3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;
D) heterocyclic compounds
- pyridines: fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine, 2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine,
3,4,5-trichloropyridine-2,6-di-carbonitrile, N-(1 -(5-bromo-3-chloro-pyridin-2- yl)-ethyl)-2,4-dichloronicotinamide, N-[(5-bromo-3-chloro-pyridin-2-yl)- methyl]-2,4-dichloro-nicotinamide;
- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;
- piperazines: triforine;
- pyrroles: fenpiclonil, fludioxonil;
- morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
- piperidines: fenpropidin;
- dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
- non-aromatic 5-membered heterocycles: famoxadone, fenamidone, fluti- anil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3- dihydro-pyrazole-1 -carbothioic acid S-allyl ester;
- others: acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasti- cidin-S, captafol, captan, chinomethionat, dazomet, debacarb, di- clomezine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tri- cyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, 5-chloro-1 -(4,6- dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole and 5-chloro-7-(4- methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo- [1 ,5-a]pyrimidine;
E) carbamates
- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasul- phocarb, metiram, propineb, thiram, zineb, ziram;
- carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb, propamocarb hydrochlorid, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
F) other active substances
- guanidines: guanidine, dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
- antibiotics: kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, polyoxine, validamycin A;
- nitrophenyl derivates: binapacryl, dinobuton, dinocap, nitrthal-isopropyl, tecnazen,
organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
- sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;
- organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; - organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro- 2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
- inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
- others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin,
metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxam- ine, tebufloquin, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoro- methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro- 3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl forma- midine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N- ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethyl- silanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N'-(5- difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N- methyl formamidine,
2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)- amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-
4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen- 1 -yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin- 4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)- acetyl]-piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thi- azolecarboxamide;
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flu- metralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, pro- hexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapen- thenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid , trinexapac- ethyl and uniconazole;
H) herbicides
- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproani- lide, 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, dime- piperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, seth- oxydim, tepraloxydim, tralkoxydim;
- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodia- mine, trifluralin;
- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fome- safen, lactofen, oxyfluorfen;
- hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
- imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, ima- zaquin, imazethapyr; - phenoxy acetic 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, flu- roxypyr, picloram, picolinafen, thiazopyr;
- sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron- ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, fla- zasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron- methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfu- ron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 -((2-chloro-6- propyl-imidazo[1 ,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2- yl)urea;
- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazi- none, metamitron, metribuzin, prometryn, simazine, terbuthylazine, ter- butryn, triaziflam;
- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron,tebuthiuron;
- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam- methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, or- tho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, py- roxasulfone, pyroxsulam;
- others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicy- clopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, car- fentrazone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fen- trazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flur- tamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclo- nil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quino- clamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3- methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)- phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2- cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2- cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4- chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)- pyridine-2-carboxylic acid methyl ester;
I) insecticides
- organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl,
chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, di- crotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, car- bofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, ox- amyl, pirimicarb, propoxur, thiodicarb, triazamate;
- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cy- permethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imi- prothrin, 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: chlor- fluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflu- muron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, dio- fenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spi- rodiclofen, spiromesifen, spirotetramat;
- nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefu- ran, 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, le- pimectin, spinosad, spinetoram;
- mitochondrial electron transport inhibitor (METI) 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;
- sodium channel blockers: indoxacarb, metaflumizone;
- others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86), cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistriflu- ron, and pyrifluquinazon; in a synergistically effective amount. 2. The mixture according to claim 1 , comprising a compound I and a compound II in a weight ratio of from 1000:1 to 1 :1 .
3. The mixture according to claim 1 or 2, wherein A is -CO-.
4. The mixture according to any of the claims 1 to 3, wherein X is CH3.
5. The mixture according to any of the claims 1 to 4, wherein Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6 to 18 carbon atoms.
6. The mixture according to claim 5, wherein Ac is selected from acyl radicals of alkyl or alkenyl carboxylic acids having 6 carbon atoms (caproyi), 8 carbon atoms (capryloyl), 10 carbon atoms (decanoyl), 12 carbon atoms (lauroyl) and 14 carbon atoms (myristoyl).
7. The mixture according to any of the claims 1 to 6, wherein n is 1 , 2 or 3.
8. The mixture according to any of the claims 1 to 7, wherein the agriculturally acceptable salt of compound I is a Na, K, Ca, Mg, Fe(ll), Zn, NH4, or Cu(ll) salt.
9. The mixture according to any of the claims 1 to 8, wherein compound I is sodium stearoyl lactylate.
10. The mixture according to any of the claims 1 to 9, wherein component 2) is at least one compound II selected from pyraclostrobin, kresoxim-methyl, azox- ystrobin, fluoxastrobin, trifloxystrobin, enestroburin and pyribencarb.
1 1 . The mixture according to any of the claims 1 to 10 comprising at least two active compounds II.
12. An agrochemical composition wherein said composition comprises a solvent or solid carrier and a mixture according to any of the claims 1 to 1 1.
13. A method for combating harmful fungi, comprising:
treating the fungi or the plants, the soil or seeds to be protected against fungal attack with an effective amount of the mixtures as defined in any of the claims 1 to 1 1 , or a composition as defined in claim 12.
14. The use of the mixtures as defined in any of claims 1 to 1 1 , for protecting plant propagation material, seed, the seedlings' roots and shoots from infestation by harmful fungi.
15. Seed coated with a mixture as defined in any of the claims 1 to 1 1 , or a composition as defined it claim 12, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
PCT/EP2010/062565 2009-09-01 2010-08-27 Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi Ceased WO2011026796A1 (en)

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CN105494387A (en) * 2015-12-16 2016-04-20 江苏辉丰农化股份有限公司 Pesticide composition
WO2016121354A1 (en) * 2015-01-26 2016-08-04 国立研究開発法人農業・食品産業技術総合研究機構 Soil-borne disease control method, soil for plant cultivation use, and soil-borne disease control agent
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