WO2018202737A1 - Fungicidal mixtures comprising triazole compounds - Google Patents

Fungicidal mixtures comprising triazole compounds Download PDF

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Publication number
WO2018202737A1
WO2018202737A1 PCT/EP2018/061249 EP2018061249W WO2018202737A1 WO 2018202737 A1 WO2018202737 A1 WO 2018202737A1 EP 2018061249 W EP2018061249 W EP 2018061249W WO 2018202737 A1 WO2018202737 A1 WO 2018202737A1
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WIPO (PCT)
Prior art keywords
methyl
phenyl
chloro
ethyl
carboxamide
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PCT/EP2018/061249
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French (fr)
Inventor
Jens Bruns
Dieter Strobel
Frederik Menges
Original Assignee
Basf Se
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Publication date
Application filed by Basf Se filed Critical Basf Se
Priority to EP18721791.4A priority Critical patent/EP3618628A1/en
Priority to BR112019022206-5A priority patent/BR112019022206A2/en
Publication of WO2018202737A1 publication Critical patent/WO2018202737A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to fungicidal mixtures comprising, as active components, 1 ) at least one triazole compound of the formula I
  • R 1 is hydrogen, chlorine, methyl, difluoromethyl or SFs:
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen, chlorine or trifuoromethyl
  • R 4 is hydrogen, chlorine or trifluoromethyl, or an N-oxide, or an agriculturally useful salt thereof;
  • Inhibitors of complex III at Q 0 site azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1.12), picoxystrobin (A.1 .13), pyraclostrobin (A.1 .14),
  • pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3- (2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- N-methyl-acetamide (A.1 .18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1.21 ), fenamidone (A.1 .22), methyl-/V-[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.23), 1-[3- chloro-2-[[1 -(4-chlorophenyl)-1 H-pyrazol-3-yl]
  • binapacryl A.4.2
  • dinobuton A.4.3
  • dinocap A.4.4
  • fluazinam A.4.5
  • fentin salts e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);
  • ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
  • C14 demethylase inhibitors triazoles: azaconazole (B.1 .1 ), bitertanol (B.1.2), bromuconazole (B.1 .3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1 .14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (
  • Delta 14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • Sterol biosynthesis inhibitors chlorphenomizole (B.4.1 );
  • phenylamides or acyl amino acid fungicides benalaxyl (C.1 .1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1.6), oxadixyl (C.1 .7);
  • nucleic acid synthesis inhibitors hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2- (p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
  • tubulin inhibitors benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6- methyl-5-phenyl-pyridazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine (D.1 .7), N-ethyl-2-[(3-ethynyl-8-methyl-6- quinolyl)oxy]butanamide (D.1 .8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2- methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-
  • diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
  • methionine synthesis inhibitors cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);
  • blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
  • MAP / histidine kinase inhibitors fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);
  • G protein inhibitors quinoxyfen (F.2.1 );
  • Phospholipid biosynthesis inhibitors edifenphos (G.1 .1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
  • lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
  • propamocarb (G.4.1 );
  • oxathiapiprolin G.5.1
  • 2- ⁇ 3-[2-(1- ⁇ [3,5- bis(difluoromethyl-1 H-pyrazol-1-yl]acetyl ⁇ piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5-yl ⁇ phenyl methanesulfonate G.5.2
  • 2- ⁇ 3-[2-(1- ⁇ [3,5-bis(difluoromethyl)- 1 H-pyrazol-1 -yl]acetyl ⁇ piperidin-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ -3- chlorophenyl methanesulfonate G.5.3
  • thio- and dithiocarbamates ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
  • organochlorine compounds anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
  • guanidine H.4.1
  • dodine H.4.2
  • inhibitors of glucan synthesis validamycin (1.1 .1 ), polyoxin B (1.1 .2); melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
  • bronopol K.1 .1
  • chinomethionat K.1.2
  • cyflufenamid K.1.3
  • cymoxanil K.1 .4
  • dazomet K.1.5
  • debacarb K.1 .6
  • diclocymet K.1.7
  • diclomezine K.1.8
  • difenzoquat K.1.9
  • difenzoquat-methylsulfate K.1.10, diphenylamin (K.1 .1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1 .13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1 .17), methasulfocarb (K.1.18), nitrapyrin
  • activator activity Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var.
  • amyloliquefaciens Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, DHophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f .
  • catenulate also named Gliocladium catenulatum
  • Gliocladium roseum also named Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor a/bus
  • Paenibacillus alvei Paenibacillus polymyxa
  • Pantoea vagans Penicillium bilaiae
  • Phlebiopsis gigantea Pseudomonas sp.
  • Pseudomonas ch/oraphis Pseudozyma flocculosa
  • Pichia a noma la Pythium oligandrum
  • Sphaerodes mycoparasitica Streptomyces griseoviridis, S.
  • T. asperellum T. atroviride
  • T. fertile T. gamsii
  • T. harmatum T. harzianum
  • T. polysporum T.
  • Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity harpin protein, Reynoutria sachalinensis extract;
  • Agrobacterium radiobacter Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp.
  • Cryptoph/ebia leucotreta granu ⁇ ov ⁇ rus (CrleGV), Flavobacterium spp., Helicoverpa nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV),
  • Heterorhabditis bacteriophora Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acrid um, Nomuraea rileyi, Paecilomyces fumosoroseus, P. niacin us, Paenibacillus popilliae, Pasteur/a spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P.
  • Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium melilotr,
  • abscisic acid M.1 .1
  • amidochlor amidochlor
  • ancymidol 6-benzylaminopurine
  • brassinolide butralin
  • chlormequat chlormequat chloride
  • choline chloride cyclanilide
  • daminozide dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
  • Lipid biosynthesis inhibitors alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • N.2 ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,
  • flucetosulfuron flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron
  • N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl; triafamone; N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine,
  • N.4 protoporphyrinogen-IX oxidase inhibitors acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone- ethyl, chlormethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-eth
  • N.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone,
  • N.6 EPSP synthase inhibitors glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);
  • Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium,
  • glufosinate glufosinate-P, glufosinate-ammonium
  • Mitosis inhibitors benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam;
  • N.10 VLCFA inhibitors acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napropamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, 11.3, II.4, II.5, II.6, II.7, II.8 and II.9
  • Cellulose biosynthesis inhibitors chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3- ylamine (CAS 175899-01 -1 );
  • Decoupler herbicides dinoseb, dinoterb, DNOC and its salts
  • Auxinic herbicides 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salt
  • N.14 Auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, naptalam and
  • Acetylcholine esterase (AChE) inhibitors aldicarb, alanycarb, bendiocarb,
  • EPN EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep,
  • GABA-gated chloride channel antagonists endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;
  • Sodium channel modulators acrinathrin, allethrin, d-cis-trans allethrin, d-trans
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin,
  • Nicotinic acetylcholine receptor allosteric activators spinosad, spinetoram;
  • Chloride channel activators abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;
  • miscellaneous non-specific (multi-site) inhibitors methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
  • Bacillus thuringiensis Bacillus sphaericus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,
  • Inhibitors of mitochondrial ATP synthase diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers bensultap, cartap
  • Inhibitors of the chitin biosynthesis type 0 bistrifluron, chlorfluazuron,
  • Ecdyson receptor agonists methoxyfenozide, tebufenozide, halofenozide,
  • fufenozide chromafenozide
  • Octopamin receptor agonists amitraz
  • Mitochondrial complex I electron transport inhibitors fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
  • Mitochondrial complex IV electron transport inhibitors aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
  • Mitochondrial complex II electron transport inhibitors cyenopyrafen, cyflumetofen;
  • Ryanodine receptor-modulators flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole;
  • R -3-chloro-N1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluoro-1- (trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamide
  • S -3- chloro-N1- ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-( ⁇ [3-bromo-1-(3- chloropyri
  • afidopyropen afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,
  • cyclopropanecarboxylate in a weight ratio of from 100:1 to 1 :100.
  • the invention also relates to a method for controlling phytopathogenic harmful fungi using mixtures of at least one compound I and at least one compound I I; to the use of compounds I and compounds II for controlling phytopathogenic harmful fungi; to agrochemical
  • compositions comprising these mixtures; and to agrochemical compositions further comprising seed.
  • Compounds I and their preparation and their use as fungicidally active compounds have been described in WO 2017/029179. Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound in the control of harmful fungi leads in many cases to a rapid selection of those fungus strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi with the active compound in question is then no longer possible.
  • mixtures of different active compounds are conventionally employed for controlling harmful fungi.
  • active compounds having different mechanisms of action it is possible to ensure successful control over a relatively long period of time.
  • compositions comprising at least one compound I and at least one compound II .
  • Agriculturally acceptable 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 ammonium ion which, if desired, may carry 1 to 4 Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably
  • trimethylbenzylammonium furthermore phosphonium ions, sulfonium ions, preferably tri(Ci- C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the scope of the present invention includes mixtures of the (R)- and (S)-isomers and the racemates of compounds I and/or II having one or more chiral centers.
  • atrope isomers of compounds I and/or II may be present. They also form part of the subject matter of the invention.
  • the active substances referred to as compounds II, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci.
  • Particularly preferred compounds I are those with R 2 being hydrogen and either R 3 is hydrogen and R 4 is trifluoromethyl or R 3 is trifluoromethyl and R 4 is hydrogen.
  • mixtures and compositions thereof according to the invention can, in the use form as fungicides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until 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).
  • the mixtures comprise a compound I and a compound II and, as component 3), a further active compound II, resulting in a ternary mixtures, preferably in a synergistically effective amount.
  • One embodiment of the invention relates to those ternary mixtures of a compound I and two different compounds (II).
  • the components 1 ) and 2) in these mixtures are present in a synergistically effective amount.
  • the invention also relates to a method for controlling phytopathogenic harmful fungi using the abovementioned ternary mixtures; to agrochemical compositions comprising these ternary mixtures; and to agrochemical compositions further comprising seed comprising these mixtures.
  • compositions only two active compounds as defined are present in these compositions (herein also called “binary compositions").
  • the composition may, of course, contain any kind of additive or the like as detailed below in order to provide a formulation suitable for use in agriculture.
  • the weight ratio of component I to component II depends from the properties of the active substances used and is usually in the range of from 1 :1000 to 1000:1 , more particularly 1 :500 to 500:1.
  • the weight ratio of component I to component II generally depends from the properties of the active substances used and is usually in the range of from 1 :100 to 100:1 , frequently in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , particularly preferably in the range of from 1 :10 to 10:1 , in particular in the range of from 1 :3 to 3:1. It may also be preferable for the weight ratio to be in the range of from 1 :2 to 2:1.
  • the weight ratio of component I to component II usually is in the range of from 100:1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
  • the weight ratio of component I to component II usually is in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
  • component I is as defined above and component II is selected from any one of groups A) to K).
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detained above, and component II is selected from group A) of the respiration inhibitors.
  • component II is selected from the group of inhibitors of complex III at Q 0 site, in e.g. the strobilurins.
  • component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, fenamidone, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]- 4-methyl-tetrazol-5-one, (2 ⁇ 2 )-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyiminc>- /V3-dimethyl-pent-3-enamide and (Z ⁇ 2 )-5-[1 ⁇ (4-chlorophenyl)pyrazol ⁇ 3-yl]oxy-2- methoxyimino- V,3-dimethyl-pent-3-enamide.
  • azoxystrobin dim
  • component II is selected from the group of inhibitors of complex II, e.g. carboxamides.
  • component II is selected from the group consisting of benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad and sedaxane.
  • component II is selected from the group of ametotradin, cyazofamid, fluazinam, fentin salts such as fentin acetate.
  • these are binary compositions which, as active compounds, comprise in each case only the mentioned two active components.
  • component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group B) of the sterol biosynthesis inhibitors (SBI fungicides).
  • component II is selected from the group of the C14 demethylase inhibitors (DMI fungicides), selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadi- mefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, fenarimol and triforine.
  • DI fungicides selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadi- mefon, triadi
  • component II is selected from the group of the delta14-reductase inhibitors, in particular dodemorph, fenpropimorph, tridemorph, fenpropidin and spiroxamine. According to a further embodiment thereof, component II is selected from the group of Inhibitors of 3-keto reductase such as fenhexamid.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group C) of the Nucleic acid synthesis inhibitors and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group D) of the inhibitors of cell division and cytoskeleton, such as benomyl, carbendazim, thiophanate- methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone, in particular ethaboxam, zoxamide and metrafenone.
  • the inhibitors of cell division and cytoskeleton such as benomyl, carbendazim, thiophanate- methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone, in particular ethaboxam, zoxamide and metrafenone.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group E) of the inhibitors of amino acid and protein synthesis, in particular selected from cyprodinil, mepanipyrim and pyrimethanil.
  • component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group F) of the signal transduction inhibitors, in particular selected from iprodione, fludioxonil, vinclozolin and quinoxyfen.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group G) of the lipid and membrane synthesis inhibitors, such as dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid and propamocarb.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group H) of the inhibitors with Multi Site Action, in particular selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone, more particularly selected from captan, Bordeaux mixture, copper hydroxide
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group I) of the cell wall synthesis inhibitors, in particular selected from carpropamid and fenoxanil.
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group J) of the plant defence inducers, in particular selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl, fosetyl-aluminium, phosphorous acid and salts thereof such as potassium salt of phosphorous acid, sodium salt of phosphorous acid, calcium salt of phosphorous acid, lithium salt of phosphorous acid and aluminium salt of phosphorous acid.
  • group J of the plant defence inducers, in particular selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl, fosetyl-aluminium, phosphorous acid and salts thereof such as potassium salt of phosphorous acid, sodium salt of phosphorous acid, calcium salt of phosphorous acid, lithium salt of phosphorous acid and aluminium salt of phosphorous acid
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group K), in particular selected from cymoxanil, proquinazid, /V-methyl-2- ⁇ 1 -[(5-methyl-3-trifluoromethyl- 1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl ⁇ -/V-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1-yl]- 4-thiazolecarboxamide, N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N- [(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide,
  • component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group L) (antifungal biocontrol agents and plant bioactivators), in particular selected from Bacillus subtilis strain NRRL No. B-21661 , Bacillus umilus strain NRRL No. B-30087 and Ulocladium oudemansii .
  • group L antifungal biocontrol agents and plant bioactivators
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group M) (growth regulators).
  • the growth regulator is selected from chlormequat (chlormequat chloride), mepiquat (mepiquat chloride),
  • paclobutrazole prohexadione (prohexadione-calcium), trinexapac-ethyl and uniconazole.
  • the composition comprises i.e in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F (component I), and a component II selected from pyraclostrobin, fluxapyroxad, fenpropimorph, prothioconazole and chlorothalonil in a weight ratio from 1 :20 to 20:1 , particularly preferably in the range of from 1 :10 to 10:1 , in particular in the range of from 1 :3 to 3:1 . It may also be preferable that the weight ratio is in the range of from 1 :2 to 2:1.
  • these compositions are "binary composition” that is, in the sense of the present invention, a composition, wherein only the said two active compounds are present.
  • the composition may, of course contain any kind of additive or the like as detailed below in order to provide a formulation suitable for use in agriculture.
  • Said two-component compositions comprising two fungicides as components I and II are in particular suitable as fungicides as detailed below.
  • said compositions are used for the control of cereal pathogens.
  • said compositions are suitable for controlling wheat pathogens.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 2:1.
  • Said compositios are particularly suitable for controlling the wheat pathogens selected from Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis.
  • composition is useful for the control of the pathogens selected from Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides.
  • said compositions are used for controlling barley pathogens.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 2:1.
  • Said compositions are particularly suitable for controlling the barley pathogens, selected from Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis.
  • said compositions are useful for controlling the barley pathogens, selected from Ramularia collo-cygni and Pseudocercosporella herpotrichoides.
  • said compositions are used for the control of soy pathogens.
  • soy pathogens especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 3:1 to 1 :3, wherein it may be especially preferred if component I to II is present 3:1 to 2:1.
  • said compositions are suitable for controlling soy pathogens selected from phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa.
  • said compositions may also be effectively used for the control of the so-called FDC (Foliar Disease Complex), e.g. against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..
  • said compositions are used for the control of corn pathogens.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
  • said compositions are suitable for controlling corn pathogens selected from Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.
  • said compositions are used for the control of sugar beet pathogens.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
  • said compositions are suitable for controlling corn pathogens selected from Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
  • compositions are used for the control of oil seed rape and canola pathogens, in particular selected from Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.
  • canola pathogens in particular selected from Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
  • said compositions are used for the control of rice pathogens, in particular selected from Rhizoctonia solani and Pyricularia oryzae.
  • rice pathogens in particular selected from Rhizoctonia solani and Pyricularia oryzae.
  • especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
  • Said compositions of component I and II is also suitable for the control of pathogens in specialty crops, such as turf, potato, tomato, cucurbits, grapes, apples, ornamentals and bananas.
  • Turf pathogens that may be controlled according to the present invention are selected from Sclerotinia homeocarpa and Rhizoctonia solani. When used in turf, especially preferred weight ratios of the active ingredients are 20:1 bis 1 :20, in particular 2:1 bis 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 1 :2.
  • Potato and tomato pathogens that may be controlled according to the present invention are in particular selected from Alternaria solani, A. alternata and Rhizoctonia solani.
  • a cucurbit pathogen that may be controlled according to the present invention is in particular Sphaerotheca fuliginea.
  • a grape pathogen that may be controlled according to the present invention is in particular Uncinula necator and Botrytis cinerea.
  • An apple pathogen that may be controlled according to the present invention is in particular Podosphaera leucotricha and Venturia inaequalis.
  • Ornamental pathogens that may be controlled according to the present invention are in particular selected from Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp.
  • Banana pathogens that may be controlled according to the present invention are in particular selected from Mycosphaerella fijiensis and Mycosphaerella musicola.
  • a specific embodiment of the above embodiment relates to the composition, comprising component I and fluxapyroxad as component II in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2.
  • this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
  • compositions comprising component I and as component II pyraclostrobin in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2.
  • this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
  • compositions comprising component I and as component II fenpropimorph in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2.
  • this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
  • a further specific embodiment of the above two-component ompositions relates to the composition, comprising component I and as component II chlorothalonil in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2.
  • this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
  • component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group N) (herbicides).
  • component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group O) (insecticides).
  • the insecticide is selected from the group of the organo(thio)phosphates, in particular selected from the group consisting of acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl-parathion, monocrotophos, phorate, profenofos and terbufos.
  • the insecticide is selected from the group of the carbamates, in particular selected from the group consisting of aldicarb, carbaryl, carbofuran, carbosulfan, methomyl and thiodicarb.
  • the insecticide is selected from the group of the pyrethroids, in particular selected from the group consisting of: bifenthrin, cyfluthrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, lambda-cyhalothrin and tefluthrin.
  • the insecticide is selected from the group of insect growth regulators, in particular selected from the group consisting of lufenuron and spirotetramat.
  • the insecticide is selected from the group of the nicotine receptor agonists/antagonists, in particular selected from the group consisting of:
  • the insecticide is selected from the group of the GABA antagonists, in particular selected from the group consisting of: endosulfan and fipronil.
  • the insecticide is selected from the group of the macrocyclic lactones, in particular selected from the group consisting of: abamectin, emamectin, spinosad and spinetoram.
  • the insecticide is hydramethylnon.
  • the insecticide is fenbutatin oxide.
  • the insecticide is selected from the group consisting of chlorfenapyr, indoxacarb, metaflumizone, flonicamid, flubendiamide, cyazypyr (HGW86) and cyflumetofen.
  • component II is selected from the following fungicide compounds: azoxystrobin (A.1 .1 ), dimoxystrobin (A.1 .4), famoxadone (A.1 .21 ), fenamidone (A.1.22), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl- phenyl]-4-methyl-tetrazol-5-one (A.1.26), (Z,2£)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2- methoxyimino-/Vi3-dirnethyl-pent-3-enamide (A.1 .34), (Zi2iE)-5-[1 -(4-chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino- V,3-dimethyl-pent-3-enamide
  • compositions according to the invention are compiled in Table B, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • component II is selected from the following fungicide compounds: fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), orysastrobin (A.1 .12), pyraclostrobin (A.1.14), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), isopyrazam (A.3.12), meptyldinocap (A.4.6), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1.12), ipconazole (B.1.15), metconazole (B.1.17),
  • compositions according to the invention i.e. one specific individualized composition.
  • these are binary compositions which each only contain these two components as the active compounds.
  • every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B1 Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • component II is selected from the following fungicide compounds: picoxystrobin (A.1 .13), trifloxystrobin (A.1 .17), penflufen (A.3.15), penthiopyrad (A.3.16), sedaxane (A.3.19), silthiofam (A.4.12), penconazole
  • compositions according to the invention i.e. one specific individualized composition.
  • these are binary compositions which each only contain these two components as the active compounds.
  • every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B2 Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients. compoI II compoI II compoI II sition sition sition sition
  • component II is selected from the following fungicide compounds: Bordeaux mixture (H.1.1 ), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), maneb (H.2.3), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10). Consequently, further particularly preferred two-component compositions are compiled in Table B2a, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B2a Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ration (S):(R).
  • the respective component I is present as (S) enantiomer.
  • the respective component I is present as (R) enantiomer.
  • component II is selected from the following fungicides: azoxystrobin (A.1.1 ), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), pyraclostrobin (A.1.14), trifloxystrobin (A.1.17), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), fluxapyroxad (A.3.9), isopyrazam (A.3.12), penthiopyrad (A.3.16), fluazinam (A.4.5), difenoconazole (B.1.5), epoxiconazole (B.1.8), flusilazole (B.1 .1 1 ), metconazole (B.1 .17), propiconazole (B.1 .22), prothioconazole (B.1 .23), tebuconazole (B.1.25), prochloraz (B
  • component II is selected from the following fungicides: fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), pyraclostrobin (A.1 .14), trifloxystrobin (A.1.17),
  • component II is selected from the following growth regulators: mepiquat chloride, chlormequat chloride, trinexapac-ethyl, prohexadione-calcium, ethephon. Consequently, particularly preferred two-component compositions are compiled in Table B3, wherein each row corresponds to one embodiment of the compositions according to the invention. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B3 Two-component compositions comprising one component I and one growth regulator as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R).
  • the respective component I is present as (S) enantiomer.
  • component I is present as (R) enantiomer.
  • component II is selected from the following herbicides: glyphosate, imazamox, dicamba, glufosinate, imazapic, imazapyr, imazethapyr.
  • compositions according to the invention are compiled in Table B4, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B4 Two-component compositions comprising one component I and one herbicide as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R).
  • the respective component I is present as (S) enantiomer. According to a further particular embodiments of the invention, the respective component I is present as (R) enantiomer.
  • component II is selected from the following insecticides: abamectin, acephate, acetamiprid, aldicarb, alpha-cypermethrin, betacyfluthrin, bifenthrin, carbofuran, chlorfenapyr, chlorpyrifos, clothianidin, cyazypyr, cyflumetofen, deltamethrin, dimethoate, dinotefuran, endosulfan, esfenvalerate, fenbutatin oxide, fipronil, flonicamid, flubendiamide, hydramethylnon, imidacloprid, indoxacarb, lambda- cyhalothrin, metaflumizon, methamidophos, metoxyfenozide, nitenpyram, pirimicarb, pymetrozine, pyridabene, rynaxapyr,
  • component II is selected from the following insecticides: abamectin, acetamiprid, alpha-cypermethrin, betacyfluthrin, b
  • compositions according to the invention are compiled in Table B5, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
  • Table B5 Two-component compositions comprising one component I and one insecticide as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
  • the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R). According to particular embodiments of the invention, the respective component I is present as (S) enantiomer.
  • the respective component I is present as (R) enantiomer.
  • the present invention relates to three-component compositions, i.e. compositions comprising component I, i.e a compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, one component II selected from groups A) to O) and the other component II also selected from groups A) to O), wherein both components II are not identical.
  • component II in each case is selected from the preferred groups or preferred active compounds as given above for component II.
  • compositions comprising exactly three active compounds as defined are present in these compositions (herein also called “ternary compositions").
  • the composition may, of course, contain any kind of additive or the like as detained below in order to provide a formulation suitable for use in agriculture.
  • the weight ratio of component I to the 1 st further active compound II depends on the properties of the active compounds in question and may particularly be 1000:1 to 1 :1000, specifically 500:1 to 1 :500. Preferably, it is in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :20 to 20:1 . It may be preferable for the weight ratio to be in the region of from 1 :10 to 10:1 , preferably from 1 :3 to 3:1 , in particular from 1 :2 to 2:1 .
  • the weight ratio of component I to the 2 nd further active compound II may particularly be 1000:1 to 1 :1000, specifically 500:1 to 1 :500. It is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :20 to 20:1. It may be preferable for the weight ratio to be in the region of from 1 :10 to 10:1 , preferably from 1 :3 to 3:1 , in particular from 1 :2 to 2:1.
  • the weight ratio of 1 st further active compound II to 2 nd further active compound II is preferably in the range of from 1 :100 to 100:1 , frequently in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , and in particular in the range of from 1 :10 to 10:1 . It may be preferable for the weight to be in the range of from 1 :3 to 3:1 , in particular from 1 :2 to 2:1.
  • the present invention relates to three-component compositions, comprising a component I, i.e a compound I, in particular a compound selected from
  • One specific embodiment relates to three-component compositions, wherein component I is as defined above and one component II is selected from group A) of the respiration inhibitors of complex III at Q 0 site and the second component II is selected from the group of B) of the sterol biosynthesis inhibitors (SBI fungicides).
  • one component II is selected from the group of strobilurins.
  • component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • the second component II is selected from the group of the C14
  • DMI fungicides in particular selected from cyproconazole,
  • compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
  • a further specific embodiment relates to three-component compositions, wherein component I is as defined above and both components II are selected from the respiration inhibitors of complex III at Qo site, wherein components II are not the same.
  • both components II are selected from the group of the strobilurins.
  • components II are selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
  • compositions wherein component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides) and the second component II is selected from the respiration inhibitors of complex II.
  • component I is as defined above
  • one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides)
  • the second component II is selected from the respiration inhibitors of complex II.
  • one component II is selected from the group of the C14 demethylase inhibitors (DMI fungicides), in particular selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole and prochloraz.
  • DI fungicides C14 demethylase inhibitors
  • the second component II is selected from the group of the carboxamides, in particular selected from benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethyl- indan-4
  • component I is as defined above, one component II is selected the respiration inhibitors of complex III at Q 0 site and the second component II is selected from the respiration inhibitors of complex II.
  • the first component II is selected from the group of the strobilurins.
  • the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • the second component II is selected from the group of the carboxamides, in particular selected from benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluz- amide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4- carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole- 4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethylin
  • Still a further specific embodiment relates to three-component compositions, wherein
  • component I is as defined above, one component II is selected from the respiration inhibitors of complex III at Q 0 site and the second component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular Delta 14-reductase inhibitors.
  • the first component II is selected from the group of the strobilurins.
  • component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim- methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • the second component II is fenpropimorph. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
  • Still a further specific embodiment relates to three-component compositions, wherein
  • component I is as defined above, one component II is selected the respiration inhibitors of complex III at Q 0 site and the second component II is selected from the inhibitors of cell division and cytoskeleton.
  • one component II is selected from the group of the strobilurins.
  • the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • the second component II is selected from tubulin inhibitors such as carbendazim.
  • the second component II is selected from sell division inhibitors such as tubulin inhibitors such as metrafenone.
  • sell division inhibitors such as tubulin inhibitors such as metrafenone.
  • these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
  • Still a further specific embodiment relates to three-component compositions, wherein
  • component I is as defined above, one component II is selected from the respiration inhibitors of complex III at Q 0 site and the second component II is selected from the inhibitors with Multi Site Action.
  • the first component II is selected from the group of
  • the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • the second component II is selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone, in particular captan, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, (tri)basic copper sulfate, mancozeb, maneb, metiram, folpet, chlorothalonil, dithianon, dodine and 2,6-dimethyl-1 H,5H
  • Still a further specific embodiment relates to three-component compositions, wherein
  • component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular from the C14 demethylase inhibitors (DMI fungicides), and the second component II is selected from the inhibitors with Multi Site Action.
  • the first component II is selected from cyproconazole, fluquinconazole,
  • One particularly suitable component II is fluquinconazole.
  • the second component II is specifically selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone, in particular captan, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, (tri)basic copper sulfate, mancozeb, maneb, metiram, folpet,
  • Still a further specific embodiment relates to three-component compositions, wherein
  • component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular from the C14 demethylase inhibitors (DMI fungicides), and the second component II is selected from the signal transduction inhibitors.
  • SBI fungicides sterol biosynthesis inhibitors
  • DMI fungicides C14 demethylase inhibitors
  • the first component II is triticonazole and the second component II is fludioxonil.
  • the present invention relates to three-component compositions, comprising a component I, in particular a compound selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, one component II selected from groups groups A) to K) and a second component II selected from groups A) to K).
  • a component I in particular a compound selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, one component II selected from groups groups A) to K) and a second component II selected from groups A) to K).
  • the composition comprises compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.Eand I.F as component I, fluxapyroxad as component II and pyraclostrobin or fenpropimorph as second component II.
  • the inventive three-component compositions comprise compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detained above, as component I, prothioconazole as component II and fluxapyroxad, bixafen, pyraclostrobin, dimoxystrobin, picoxystrobin, fluoxastrobin, fluopyram or penflufen as second component II.
  • the compounds of the formula I or compositions comprising said compounds according to the invention and the mixtures comprising said compounds and compositions, respectively, 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 following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota (Basidiomycetes), for example, but not limited to the genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the
  • Fungi imperfect! for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora
  • Peronosporomycetes for example but not limited to the genus Peronospora, Pythium, Phytophthora
  • Plasmodiophoromycetes for example but not limited to the genus Plasmodiophora
  • Zygomycetes for example, but not limited to the genus Rhizopus.
  • Some of the compounds of the formula I and the compositions according to the invention 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 compounds I and the 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.
  • compounds I and compositions thereof, respectively 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 includes 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 compounds I 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. http://cera-gmc.org/, see GM crop database therein).
  • the compounds I, and mixtures comprising them, and agrochemical compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A brassicola or brassicae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A solan/ or A alternata), tomatoes (e. g. A so/an/ or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g.
  • a fotf/c/(anthracnose) on wheat and A horde/ on barley; B/po/ar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicoia) 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.
  • 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; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana. grey mold
  • fruits and berries e. g. strawberries
  • vegetables e. g. lettuce, carrots, celery and cabbages
  • rape flowers, vines, forestry plants and wheat
  • Bremia lactucae downy mildew
  • Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchit) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochiioboius
  • anamorph Helminthosporium of Bipolaris
  • spp. leaf spots
  • corn C. carbonum
  • cereals e. g. C. sativus, anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus, anamorph: H.
  • gossypii corn (e. g. C. gramlnlco/a: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.
  • Neonectria spp. on fruit trees, vines (e. g. C liriodendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;
  • 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, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),
  • spp. wilt, root or stem rot
  • 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. so/ani( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F.
  • Microsphaera diffusa (powdery mildew) on soybeans
  • Monilinia 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 brassicae
  • rape e. g. P. parasitica
  • onions e. g. P. destructor
  • tobacco ⁇ P. tabacina soybeans
  • soybeans e. g. P. manshurica
  • Phakopsora pachyrhizi and P. meibomiae soybean rust
  • Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora)
  • soybeans e. g. P. gregata: stem rot
  • Phoma lingam root and stem rot
  • betae root rot, leaf spot and damping-off on sugar beets
  • Phomopsis spp. on sunflowers, vines e. g. P. viticola: can and leaf spot
  • soybeans e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum
  • Physoderma maydis (brown spots) on corn; 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.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. ha/stediion sunflowers
  • Podosphaera spp. powdery mildew
  • Puccinia spp. rusts on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. horde/ (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, P. kuehnii (orange rust) on sugar cane and P.
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • Pyricularia 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); Ramularia spp., e. g. R.
  • collo-cygni Roso-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rh/zocton/a spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. so/ani (root and stem rot) on soybeans, R. so/ani (sheath blight) on rice or R.
  • Rhizoctonia spring blight on wheat or barley
  • Rhizopus sto/on/fer b ⁇ ack mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fs/ior S. sclerotiorum); 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 tucker! on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S.
  • Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (p ⁇ um pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to 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 Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • Puccinia spp. rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • the compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • the term "protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Hum/cola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as
  • Coniophora spp. Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.
  • the term "stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment.
  • stored products are timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like.
  • the combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
  • Preferably "stored products” is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • the compounds I and compositions thereof, respectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves ("greening effect")
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • the compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a fungicidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical
  • compositions are prepared in a known manner, such as described by Mollet and
  • the binary or ternary mixtures of active compounds described herein can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given herein for the compositions of compounds I.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol
  • glycols DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
  • Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e. g. cellulose, star
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e. g. iron oxide, titan oxide, iron
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I and 5-15 wt% wetting agent e. g. alcohol alkoxylates
  • a water-soluble solvent e. g. alcohols
  • a compound I and 1-10 wt% dispersant e. g. polyvinyl pyrrolidone
  • organic solvent e. g. cyclohexanone
  • EC Emulsifiable concentrates
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e. g. aromatic hydrocarbon
  • This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a compound I In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1 -2 wt% thickener e. g. xanthan gum
  • a compound I 50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound I In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • 1 -5 wt% thickener e. g. carboxymethyl cellulose
  • wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce
  • organic solvent blend e. g. fatty acid dimethyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol).
  • a polyamine e. g.
  • hexamethylenediamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • a compound I 0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%.
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • 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%, in the ready-to-use preparations.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) 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 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, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • 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.
  • a pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • a predosage device usually from a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • 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 or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • fungicide e. g. one or more fungicide from the groups A) to K
  • combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often 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 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1 .
  • the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
  • the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
  • the weight ratio of component 1 ) and component 2) depends from the properties of the active substances 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 in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) 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 in particular in the range of from 1 :4 to 4:1.
  • any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1 ).
  • 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:
  • a corresponds to the fungicidal infection of the treated plants in %
  • ⁇ 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 may be 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.
  • y efficacy expressed in % of the untreated control, when using the active compound B at the concentration b.
  • 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.

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Abstract

The present invention relates to fungicidal mixtures comprising at least one triazole compound (I) and at least one active compound (II) in a weight ratio of from 100:1 to 1 :100; to a method for controlling phytopathogenic harmful fungi using mixtures of at least one compound (I) and at least one compound (II); to the use of compounds (I) and compounds (II) for controlling phytopathogenic harmful fungi; to agrochemical compositions comprising these mixtures; and to agrochemical compositions further comprising seed.

Description

Fungicidal mixtures comprising triazole compounds Description
The present invention relates to fungicidal mixtures comprising, as active components, 1 ) at least one triazole compound of the formula I
Figure imgf000002_0001
wherein
R1 is hydrogen, chlorine, methyl, difluoromethyl or SFs:
R2 is hydrogen or chlorine;
R3 is hydrogen, chlorine or trifuoromethyl;
R4 is hydrogen, chlorine or trifluoromethyl, or an N-oxide, or an agriculturally useful salt thereof;
and
2) at least one active compound II, selected from groups A) to O):
A) Respiration inhibitors
Inhibitors of complex III at Q0 site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1.12), picoxystrobin (A.1 .13), pyraclostrobin (A.1 .14),
pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3- (2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- N-methyl-acetamide (A.1 .18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1.21 ), fenamidone (A.1 .22), methyl-/V-[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.23), 1-[3- chloro-2-[[1 -(4-chlorophenyl)-1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5- one (A.1.24), 1 -[3-bromo-2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4- methyl-tetrazol-5-one (A.1 .25), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3- methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.26), 1-[2-[[1 -(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-fluoro-phenyr}-4-methyl-tetrazol-5-one (A.1.27), 1-[2-[[1-(2,4- dichlorophenyl)pyrazol-3-yljoxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1 .28), 1 -[3-cyclopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]- methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 ,30), 1 -[3-(difluoromethoxy)-2-[[2-methyl- 4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 ,31 ), 1 - methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phen- oxy]methyl]phenyl]tetrazol-5-one (A.1 , 32), (Zi2£ -5-[1-(2,4-dichlorophenyl)pyrazol-3- yl] oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.34), (Z,2.r)-5-[1-(4- chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-A ,3-dimethyl-pent-3-enamide
(A.1 .35), pyriminostrobin (A.1 .36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl- oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1 .38);
- inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl- 4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4); inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), 3-(difluoromethyl)-1-methyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 3-(trifluoromethyl)-1 - methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 1 ,3-dimethyl-
N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)- 1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1 ,3,5- trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.26), 3- (difluoromethyl)-l ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-
4-carboxamide (A.3.28), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-5- fluoro-1 ,3-dimethyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2- methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), N-[(5-chloro-2- isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl- pyrazole-4-carboxamide (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4- yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan- 4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl- indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 - dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 - dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-
[(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2- (difluoromethyl)-N-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3- carboxamide (A.3.39);
- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates:
binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5),
meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);
ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides)
C14 demethylase inhibitors: triazoles: azaconazole (B.1 .1 ), bitertanol (B.1.2), bromuconazole (B.1 .3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1 .14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1 .21 ), propiconazole (B.1.22), prothioconazole (B.1 .23), simeconazole (B.1 .24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1 .27), triadimenol (B.1 .28), triticonazole (B.1 .29), uniconazole (B.1.30), ipfentrifluconazole, (B.1 .37), mefentrifluconazole (B.1 .38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1 ,2,4- triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1 .45), prochloraz (B.1.46), triflumizol (B.1 .47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2- fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);
Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );
Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );
C) Nucleic acid synthesis inhibitors
phenylamides or acyl amino acid fungicides: benalaxyl (C.1 .1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1.6), oxadixyl (C.1 .7);
other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2- (p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
D) Inhibitors of cell division and cytoskeleton
tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6- methyl-5-phenyl-pyridazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine (D.1 .7), N-ethyl-2-[(3-ethynyl-8-methyl-6- quinolyl)oxy]butanamide (D.1 .8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2- methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2- fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-flu- oroethyl)-2-methoxy-acetamide (D.1.1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N- propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N- propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl- N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2- fluoroethyl)-2-methylsulfanyl-acetamide (D.1 .15), 4-(2-bromo-4-fluoro-phenyl)-N-(2- chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16);
other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
E) Inhibitors of amino acid and protein synthesis
methionine synthesis inhibitors: cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);
protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
F) Signal transduction inhibitors
MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);
G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors
Phospholipid biosynthesis inhibitors: edifenphos (G.1 .1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1-{[3,5- bis(difluoromethyl-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)- 1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3- chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-
1- yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5- bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1 - yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1 -[2-[5- cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-
2- carboxamide (G.5.7), 4-[1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3- (trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.9), 4-[1 -[2-[3,5-bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3- (trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.1 1 );
H) Inhibitors with Multi Site Action
- inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1.2), copper acetate (H.1 .3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);
thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base
(H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)- tetraone (H.4.10);
I) Cell wall synthesis inhibitors
inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1 .2); melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
J) Plant defence inducers
- acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1 .3), tiadinil
(J.1.4), prohexadione-calcium (J.1 .5); phosphonates: fosetyl (J.1 .6), fosetyl- aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), calcium phosphonate (J.1.1 1 ), potassium phosphonate (J.1 .12), potassium or sodium bicarbonate (J.1 .9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);
K) Unknown mode of action
bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1 .4), dazomet (K.1.5), debacarb (K.1 .6), diclocymet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1 .1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1 .13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1 .17), methasulfocarb (K.1.18), nitrapyrin
(K.1 .19), nitrothal-isopropyl (K.1 .20), tolprocarb (K.1.21 ), oxin-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1 .24), tecloftalam (K.1.25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methyl formamidine (K.1 .28), N'-[4-[[3-[(4-chlorophenyl)methyl]-
1 ,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1 .29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl- formamidine (K.1 .30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3- pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .31 ), N'-[5-bromo-6-(4-isopropyl- cyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32),
N'-[5-bromo-2-methyl-6-(1 -phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine (K.1 .34), N'-(5-difluoromethyl-2-methyl-4-(3-tri- methylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro- phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
(pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1 .38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1 .39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1 .41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxy- methyl]-2-pyridyl]carbamate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-
2- methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1 .44), 2-[2-fluoro-6-[(8- fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1 .45), quinofumelin (K.1 .47), 9- fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2- pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2- pyridyl]quinazoline (K.1.51 ), dichlobentiazox (K.1 .52), N'-(2,5-dimethyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), Nmethyl-2-{1 -[(5-methyl-3-trifluoro- methyl-1 H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-/V-[(1 R)-1 ,2,3,4-tetrahydronaphthalen- 1-yl]-4-thiazolecarboxamide (K.1.54), N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-
3- yl]benzamide (K.1.55), N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzamide (K.1 .56), N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]benzamide (K.1 .57), N-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]cyclopropanecarboxamide (K.1.58), N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (K.1 .59), 2,2-difluoro-N-methyl-2-[4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide (K.1 .60, N-allyl-N-[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (K.1 .61 ), N-[(E)-N- methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzamide (K.1.62), N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (K.1 .63),
N-allyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1 .64), 4,4-dimethyl-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one (K.1 .65), N-methyl-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzenecarbothioamide (K.1 .66), 5-methyl-1 -[[4-[5-(trifluoromethyl)-
1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.67);
L) Biopesticides
L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense
activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var.
amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, DHophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f .
catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor a/bus, Paenibacillus alvei, Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas ch/oraphis, Pseudozyma flocculosa, Pichia a noma la, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T.
stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);
L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;
L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal
activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp.
kurstaki, B. t. ssp. tenebrionis, Beauveria bass/ana, B. brongniartii, Burkho/deria spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV),
Cryptoph/ebia leucotreta granu\ov\rus (CrleGV), Flavobacterium spp., Helicoverpa nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV),
Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acrid um, Nomuraea rileyi, Paecilomyces fumosoroseus, P. niacin us, Paenibacillus popilliae, Pasteur/a spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei,
Streptomyces ga/bus, S. micro flavus,
L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1 -yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,1 1 ,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1 - butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1 -ol, (E,Z)- 2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,1 1-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1- yl acetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1-yl acetate, Z-1 1-tetradecenal, Z-
1 1 -tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract; L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium melilotr,
M) Growth regulators
abscisic acid (M.1 .1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide,
daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4- cyclo-"propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); ^'^'-dichloro^-cyclopropylll .r-biphenyll-S-y -S- hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro- 4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)- one (CAS 1033757-93-5); ^■^■-Dichloro^-ethylll .r-biphenyll-S-yl^^.e.e-tetra- methyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro- 4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran- 3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '- biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'- chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran- 3-one (CAS 1312340-82-1 ); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3- yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'- chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5- oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 ); 4-(2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran- 3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6- dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,
chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac- sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid- 1-methyhethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]-"methyl]amino]-benzoic acid propyl ester (CAS 420138-40-
5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl; triafamone; N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine,
chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron,
thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone- ethyl, chlormethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro- 4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4- trifluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452098-92-9), N tetrahydrofurfui l-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole- 1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4- trifluoromethyhphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 452099-05-7),
N tetrahydro^furfuryl-3-(2-chloro-6-fluoro-4-trifluoro^methylphenoxy)-5-methyl-1 H- pyrazole-1 -carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0),
1-methyl-6-trifluoro^methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4- [2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]- 3-methoxy-but-2-enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)- 1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS
212754-02-4);
N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone,
flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4- trifluoromethylphenyl^pyrimidine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium,
glufosinate, glufosinate-P, glufosinate-ammonium;
N.8 DHP synthase inhibitors: asulam;
N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam;
carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napropamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, 11.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000012_0003
Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3- ylamine (CAS 175899-01 -1 );
Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro- 6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9);
N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and
naptalam-sodium;
N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;
O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb,
benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, azamethiphos, azinphos- ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton,
EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos,
tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;
0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans
allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau- fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; DDT, methoxychlor;
0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin,
cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; (2E)- 1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboxi 1- [(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridine; nicotine;
0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;
0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;
0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb,
pyriproxyfen;
0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
0.9 Selective homopteran feeding blockers: pymetrozine, flonicamid;
O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;
0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaericus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,
Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient:
chlorfenapyr, DNOC, sulfluramid;
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap
hydrochloride, thiocyclam, thiosultap sodium;
0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron,
diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;
0.17 Moulting disruptors: cyromazine;
0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide,
fufenozide, chromafenozide;
0.19 Octopamin receptor agonists: amitraz;
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon,
acequinocyl, fluacrypyrim;
0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4- cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]- hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[meth- yl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen,
spirotetramat; Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen; Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-1- (trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, (S)-3- chloro-N1-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3- chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2- dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)- carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2- propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-
2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-
1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H- pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 - cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; 3-bromo- N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5- carboxamide; N-[4-chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-methylphenyl]-1- (3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; cyhalodiamide; insecticidal active compounds of unknown or uncertain mode of action:
afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,
pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 1 1 -(4-chloro- 2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1-en-10- one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3- en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3- (trifluoromethyl)-l H-1 ,2,4-triazole-5-amine, Bacillus firmus, (E/Z)-N-[1-[(6-chloro-3- pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1 -[(6-chloro-5- fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-2,2,2- trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; (E/Z)-N-[1-[(6- bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[1 -(6- chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-
3- pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-2-chloro-N-[1-[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-N-[1 -[(2-chlo- ropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.); N-[1- [(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide; N-[1 -[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'-isopropyl-acetamidine; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2- methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3- dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethylamino)-N-[2- bromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]- 2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-te- trafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;
N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; N-[3-[[[2- bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl- benzamide; 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)- ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3- fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-
(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-cyano- N-[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phen- yl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl- benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3, 3,3- hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3, 3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- benzamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5- fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]- 2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-car- boxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N- ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-methyl-N-[4- methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N,2-dimethyl-N-[4- methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-ethyl-2-methyl-N-[4- methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide; 1-[(6-chloro-3-pyri- dinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1 ,2- a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1-(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl- ethyl)pyrazole-4-carboxamide; 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N,5-di- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -[1-(1-cyanocyclopropyl)ethyl]- N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-methyl-1 -(2-fluoro-1- methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -
(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-(1 - methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4- carboxamide; 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; 2- (3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; methyl 2-
[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; N-[(2,2-di- fluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N-(2,2-diflu- oropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )-N-(2-pyrimi- dinylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]- 2-(3-pyridinyl)-2H-indazole-5-carboxamide, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N- ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4- yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide; N-[3-chloro-1-(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N- ethyl-propanamide; sarolaner, lotilaner;
0.28 [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropanecarbonyloxy)-6,12- dihydroxy-4,6a,12b-trimethyl-1 1-oxo-9-(pyridin-3-yl)-1 ,2,3,4,4a,5,6,6a,12a,12b- decahydro-1 1 H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl
cyclopropanecarboxylate; in a weight ratio of from 100:1 to 1 :100.
The invention also relates to a method for controlling phytopathogenic harmful fungi using mixtures of at least one compound I and at least one compound I I; to the use of compounds I and compounds II for controlling phytopathogenic harmful fungi; to agrochemical
compositions comprising these mixtures; and to agrochemical compositions further comprising seed. Compounds I and their preparation and their use as fungicidally active compounds have been described in WO 2017/029179. Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound in the control of harmful fungi leads in many cases to a rapid selection of those fungus strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi with the active compound in question is then no longer possible.
To reduce the risk of the selection of resistant fungus strains, mixtures of different active compounds are conventionally employed for controlling harmful fungi. By combining active compounds having different mechanisms of action, it is possible to ensure successful control over a relatively long period of time.
It is an object of the present invention to provide, with a view to effective resistance management and effective control of phytopathogenic harmful fungi, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi (synergistic mixtures) and a broadened activity spectrum, in particular for certain indications.
We have accordingly found that this object is achieved by the compositions, defined herein, comprising at least one compound I and at least one compound II .
Moreover, we have found that simultaneous, that is joint or separate, application of a compound I and a compound II or successive application of a compound I and of compound II allows better control of harmful fungi than is possible with the individual compounds alone (synergistic mixtures). Compounds I and/or the compounds II can be present in different crystal modifications, which may differ in biological activity.
Agriculturally acceptable 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 ammonium ion which, if desired, may carry 1 to 4 Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably
diisopropylammonium, tetramethylammonium, tetrabutylammonium,
trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci- C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The scope of the present invention includes mixtures of the (R)- and (S)-isomers and the racemates of compounds I and/or II having one or more chiral centers. As a result of hindered rotation of asymmetrically substituted groups, atrope isomers of compounds I and/or II may be present. They also form part of the subject matter of the invention. The active substances referred to as compounds II, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 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, WO 10/139271 , WO 1 1/028657,
WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO
13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224,
WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174,
WO 13/47441 ).
Particularly preferred compounds I are those with R2 being hydrogen and either R3 is hydrogen and R4 is trifluoromethyl or R3 is trifluoromethyl and R4 is hydrogen.
Furthermore, those compounds I are preferred, where R1 is chlorine.
Particularly preferred are compounds I.A to I.F:
I.A
Figure imgf000019_0001
Figure imgf000020_0001
Very particularly preferred are compounds I .A and I.B.
The mixtures and compositions thereof according to the invention can, in the use form as fungicides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
Mixing the compounds I and compounds II and the compositions comprising them, respectively, in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
According to the present invention, it may be preferred that the mixtures comprise a compound I and a compound II and, as component 3), a further active compound II, resulting in a ternary mixtures, preferably in a synergistically effective amount.
One embodiment of the invention relates to those ternary mixtures of a compound I and two different compounds (II). Preferably, the components 1 ) and 2) in these mixtures are present in a synergistically effective amount.
The invention also relates to a method for controlling phytopathogenic harmful fungi using the abovementioned ternary mixtures; to agrochemical compositions comprising these ternary mixtures; and to agrochemical compositions further comprising seed comprising these mixtures.
According to a specific embodiment thereof, only two active compounds as defined are present in these compositions (herein also called "binary compositions"). The composition may, of course, contain any kind of additive or the like as detailed below in order to provide a formulation suitable for use in agriculture.
The weight ratio of component I to component II depends from the properties of the active substances used and is usually in the range of from 1 :1000 to 1000:1 , more particularly 1 :500 to 500:1. The weight ratio of component I to component II generally depends from the properties of the active substances used and is usually in the range of from 1 :100 to 100:1 , frequently in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , particularly preferably in the range of from 1 :10 to 10:1 , in particular in the range of from 1 :3 to 3:1. It may also be preferable for the weight ratio to be in the range of from 1 :2 to 2:1.
According to further embodiments of the two-component compositions according to the invention, the weight ratio of component I to component II usually is in the range of from 100:1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
According to still further embodiments of the two-component compositions according to the invention, the weight ratio of component I to component II usually is in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
According to one embodiment of the two-component compositions, component I is as defined above and component II is selected from any one of groups A) to K).
One specific embodiment relates to two-component compositions, wherein component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detained above, and component II is selected from group A) of the respiration inhibitors. According to one embodiment thereof, component II is selected from the group of inhibitors of complex III at Q0 site, in e.g. the strobilurins. Specifically, component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, fenamidone, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]- 4-methyl-tetrazol-5-one, (2^2 )-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyiminc>- /V3-dimethyl-pent-3-enamide and (Z^2 )-5-[1 ~(4-chlorophenyl)pyrazol~3-yl]oxy-2- methoxyimino- V,3-dimethyl-pent-3-enamide. According to a further specific embodiment, these are binary compositions which, as active compounds, comprise in each case only the mentioned two active components.
According to a further embodiment thereof, component II is selected from the group of inhibitors of complex II, e.g. carboxamides. Specifically, component II is selected from the group consisting of benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad and sedaxane. According to a further embodiment, component II is selected from the group of ametotradin, cyazofamid, fluazinam, fentin salts such as fentin acetate. According to a further specific embodiment, these are binary compositions which, as active compounds, comprise in each case only the mentioned two active components.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group B) of the sterol biosynthesis inhibitors (SBI fungicides). According to one embodiment thereof, component II is selected from the group of the C14 demethylase inhibitors (DMI fungicides), selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadi- mefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, fenarimol and triforine. According to a further embodiment thereof, component II is selected from the group of the delta14-reductase inhibitors, in particular dodemorph, fenpropimorph, tridemorph, fenpropidin and spiroxamine. According to a further embodiment thereof, component II is selected from the group of Inhibitors of 3-keto reductase such as fenhexamid.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group C) of the Nucleic acid synthesis inhibitors and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group D) of the inhibitors of cell division and cytoskeleton, such as benomyl, carbendazim, thiophanate- methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone, in particular ethaboxam, zoxamide and metrafenone.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group E) of the inhibitors of amino acid and protein synthesis, in particular selected from cyprodinil, mepanipyrim and pyrimethanil. According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group F) of the signal transduction inhibitors, in particular selected from iprodione, fludioxonil, vinclozolin and quinoxyfen.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group G) of the lipid and membrane synthesis inhibitors, such as dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid and propamocarb.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group H) of the inhibitors with Multi Site Action, in particular selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone, more particularly selected from captan, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, (tri)basic copper sulfate, mancozeb, maneb, metiramfolpet, chlorothalonil, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group I) of the cell wall synthesis inhibitors, in particular selected from carpropamid and fenoxanil.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group J) of the plant defence inducers, in particular selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl, fosetyl-aluminium, phosphorous acid and salts thereof such as potassium salt of phosphorous acid, sodium salt of phosphorous acid, calcium salt of phosphorous acid, lithium salt of phosphorous acid and aluminium salt of phosphorous acid.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from group K), in particular selected from cymoxanil, proquinazid, /V-methyl-2-{1 -[(5-methyl-3-trifluoromethyl- 1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-/V-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1-yl]- 4-thiazolecarboxamide, N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N- [(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-[(Z)- methoxyiminomethyl]-4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-[4-[5-
(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, N-(2-fluorophenyl)-4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, 2,2-difluoro-N-methyl-2-[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]acetamide, N-allyl-N-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-N-methoxy-C-methyl- carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-allyl-N-[[4-[5-(tri- fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-1-[[4-[5-(tri- fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, N-methyl-4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide and 5-methyl-1-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group L) (antifungal biocontrol agents and plant bioactivators), in particular selected from Bacillus subtilis strain NRRL No. B-21661 , Bacillus umilus strain NRRL No. B-30087 and Ulocladium oudemansii .
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group M) (growth regulators). According to one specific embodiment, the growth regulator is selected from chlormequat (chlormequat chloride), mepiquat (mepiquat chloride),
paclobutrazole, prohexadione (prohexadione-calcium), trinexapac-ethyl and uniconazole.
According to a particular embodiment of the inventive two-component compositions comprising two fungicides, the composition comprises i.e in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F (component I), and a component II selected from pyraclostrobin, fluxapyroxad, fenpropimorph, prothioconazole and chlorothalonil in a weight ratio from 1 :20 to 20:1 , particularly preferably in the range of from 1 :10 to 10:1 , in particular in the range of from 1 :3 to 3:1 . It may also be preferable that the weight ratio is in the range of from 1 :2 to 2:1. In a particular embodiments, these compositions are "binary composition" that is, in the sense of the present invention, a composition, wherein only the said two active compounds are present. The composition may, of course contain any kind of additive or the like as detailed below in order to provide a formulation suitable for use in agriculture. Said two-component compositions comprising two fungicides as components I and II are in particular suitable as fungicides as detailed below.
According to a specific embodiment thereof, said compositions are used for the control of cereal pathogens. In particular, said compositions are suitable for controlling wheat pathogens. When used in wheat, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 2:1. Said compositios are particularly suitable for controlling the wheat pathogens selected from Septoria tritici, Stagonospora nodorum, Pyrenophora tritici repentis, Puccinia recondita, Puccinia striiformis and Blumeria graminis. Furthermore, said
composition is useful for the control of the pathogens selected from Fusarium culmorum, Fusarium graminearum and Pseudocercosporella herpotrichoides. According to a further specific embodiment, said compositions are used for controlling barley pathogens. When used in barley, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 2:1. Said compositions are particularly suitable for controlling the barley pathogens, selected from Pyrenophera teres, Rhychosporium secalis, Puccinia hordei and Blumeria graminis. Furthermore, said compositions are useful for controlling the barley pathogens, selected from Ramularia collo-cygni and Pseudocercosporella herpotrichoides.
According to a further specific embodiment, said compositions are used for the control of soy pathogens. When used in soy, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 3:1 to 1 :3, wherein it may be especially preferred if component I to II is present 3:1 to 2:1. In particular, said compositions are suitable for controlling soy pathogens selected from phakopsora pachyrizi, P. meibomiae and Microsphaera diffusa. In soy, said compositions may also be effectively used for the control of the so-called FDC (Foliar Disease Complex), e.g. against Septoria glycines, Cercospora kikuchii, C. sojina, Corynespora cassiicola and/or Alternaria spp..
According to a further specific embodiment, said compositions are used for the control of corn pathogens. When used in corn, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1. In particular, said compositions are suitable for controlling corn pathogens selected from Cercospora zeae-maydis, Puccinia sorghi and Helminthosporium maydis.
According to still a further specific embodiment, said compositions are used for the control of sugar beet pathogens. When used in sugar beet, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1. In particular, said compositions are suitable for controlling corn pathogens selected from Cercospora beticola, Erysiphe betae, Ramularia betae and Uromyces betae.
According to still a further specific embodiment, said compositions are used for the control of peanut pathogens, in particular selected from Mycosphaerella arachidis (= Cercospora) and Puccinia arachidis. When used in peanuts, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
According to still a further specific embodiment, said compositions are used for the control of oil seed rape and canola pathogens, in particular selected from Sclerotinia sclerotiorum, Leptosphearia maculans and Alternaria alternate. When used in oil seed rape or canola, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
According to still a further specific embodiment, said compositions are used for the control of rice pathogens, in particular selected from Rhizoctonia solani and Pyricularia oryzae. When used in rice, especially preferred weight ratios of the active ingredients are 20:1 to 1 :20, in particular 2:1 to 1 :2, wherein it may be especially preferred if component I to II is present 2:1 to 1 :1.
Said compositions of component I and II is also suitable for the control of pathogens in specialty crops, such as turf, potato, tomato, cucurbits, grapes, apples, ornamentals and bananas. Turf pathogens that may be controlled according to the present invention are selected from Sclerotinia homeocarpa and Rhizoctonia solani. When used in turf, especially preferred weight ratios of the active ingredients are 20:1 bis 1 :20, in particular 2:1 bis 1 :2, wherein it may be especially preferred if component I to II is present 1 :1 to 1 :2. Potato and tomato pathogens that may be controlled according to the present invention are in particular selected from Alternaria solani, A. alternata and Rhizoctonia solani. A cucurbit pathogen that may be controlled according to the present invention is in particular Sphaerotheca fuliginea. A grape pathogen that may be controlled according to the present invention is in particular Uncinula necator and Botrytis cinerea. An apple pathogen that may be controlled according to the present invention is in particular Podosphaera leucotricha and Venturia inaequalis. Ornamental pathogens that may be controlled according to the present invention are in particular selected from Sphaerotheca fuliginea, Diplocarpon spp., Alternaria spp. and Sclerotinia spp. Banana pathogens that may be controlled according to the present invention are in particular selected from Mycosphaerella fijiensis and Mycosphaerella musicola.
A specific embodiment of the above embodiment relates to the composition, comprising component I and fluxapyroxad as component II in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2. Surprisingly, this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
A further specific embodiment of the above two-component compositions relates to the composition, comprising component I and as component II pyraclostrobin in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2. Surprisingly, this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
A further specific embodiment of the above two-component compositions relates to the composition, comprising component I and as component II fenpropimorph in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2. Surprisingly, this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
A further specific embodiment of the above two-component ompositions relates to the composition, comprising component I and as component II chlorothalonil in a weight ratio of 20:1 to 1 :20, more specifically 5:1 to 1 :5, in particular 3:1 to 1 :3, more specifically 2:1 to 1 :2. Surprisingly, this composition shows synergistical effects and the components are in particular used in synergistically effective amounts.
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group N) (herbicides).
According to a further embodiment of the two-component compositions, component I is as defined above, in particular selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, and component II is selected from any one of group O) (insecticides). According to one specific embodiment, the insecticide is selected from the group of the organo(thio)phosphates, in particular selected from the group consisting of acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl-parathion, monocrotophos, phorate, profenofos and terbufos.
According to a further specific embodiment, the insecticide is selected from the group of the carbamates, in particular selected from the group consisting of aldicarb, carbaryl, carbofuran, carbosulfan, methomyl and thiodicarb. According to a further specific embodiment, the insecticide is selected from the group of the pyrethroids, in particular selected from the group consisting of: bifenthrin, cyfluthrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, lambda-cyhalothrin and tefluthrin. According to still a further specific embodiment, the insecticide is selected from the group of insect growth regulators, in particular selected from the group consisting of lufenuron and spirotetramat. According to still a further specific embodiment, the insecticide is selected from the group of the nicotine receptor agonists/antagonists, in particular selected from the group consisting of:
clothianidin, imidacloprid, thiamethoxam and thiacloprid. According to a further specific embodiment, the insecticide is selected from the group of the GABA antagonists, in particular selected from the group consisting of: endosulfan and fipronil. According to a further specific embodiment, the insecticide is selected from the group of the macrocyclic lactones, in particular selected from the group consisting of: abamectin, emamectin, spinosad and spinetoram. According to a further specific embodiment, the insecticide is hydramethylnon. According to a further specific embodiment, the insecticide is fenbutatin oxide. According to a further specific embodiment, the insecticide is selected from the group consisting of chlorfenapyr, indoxacarb, metaflumizone, flonicamid, flubendiamide, cyazypyr (HGW86) and cyflumetofen.
According to a preferred embodiment of the invention, component II is selected from the following fungicide compounds: azoxystrobin (A.1 .1 ), dimoxystrobin (A.1 .4), famoxadone (A.1 .21 ), fenamidone (A.1.22), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl- phenyl]-4-methyl-tetrazol-5-one (A.1.26), (Z,2£)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2- methoxyimino-/Vi3-dirnethyl-pent-3-enamide (A.1 .34), (Zi2iE)-5-[1 -(4-chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino- V,3-dimethyl-pent-3-enamide (A.1 .35), cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fluazinam (A.4.5), ametoctradin (A.4.1 1 ), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1.6), epoxiconazole (B.1 .8), dodemorph (B.2.2), fenpropimorph (B.2.4), fenpropidin (B.2.6), fenhexamid (B.3.1 ), carbendazim (D.1 .2), ethaboxam (D.2.2), cyprodinil (E.1 .1 ), dimethomorph (G.3.1 ), benthiavalicarb (G.3.5), copper (H.1.2), copper hydroxide (H.1.4), chlorothalonil (H.3.2), captan (H.3.4), dodine (H.4.2), dithianon (H.4.9), cyflufenamid (K.1 .3), cymoxanil (K.1 .4).
Consequently, particularly preferred two-component compositions are compiled in Table B, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B: Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
compoI II compoI II compoI II sition sition sition
B-1 I. A A.1.1 B-26 I.B A.1.26 B-51 I.C A.2.2
B-2 I.B A.1.1 B-27 I.C A.1.26 B-52 I.D A.2.2
B-3 I.C A.1.1 B-28 I.D A.1.26 B-53 I.E A.2.2
B-4 I.D A.1.1 B-29 I.E A.1.26 B-54 I.F A.2.2
B-5 I.E A.1.1 B-30 I.F A.1.26 B-55 I. A A.2.3
B-6 I.F A.1.1 B-31 I. A A.1.34 B-56 I.B A.2.3
B-7 I. A A.1.4 B-32 I.B A.1.34 B-57 I.C A.2.3
B-8 I.B A.1.4 B-33 I.C A.1.34 B-58 I.D A.2.3
B-9 I.C A.1.4 B-34 I.D A.1.34 B-59 I.E A.2.3
B-10 I.D A.1.4 B-35 I.E A.1.34 B-60 I.F A.2.3
B-1 1 I.E A.1.4 B-36 I.F A.1.34 B-61 I. A A.3.2
B-12 I.F A.1.4 B-37 I. A A.1.35 B-62 I.B A.3.2
B-13 I. A A.1.21 B-38 I.B A.1.35 B-63 I.C A.3.2
B-14 I.B A.1.21 B-39 I.C A.1.35 B-64 I.D A.3.2
B-15 I.C A.1.21 B-40 I.D A.1.35 B-65 I.E A.3.2
B-16 I.D A.1.21 B-41 I.E A.1.35 B-66 I.F A.3.2
B-17 I.E A.1.21 B-42 I.F A.1.35 B-67 I. A A.3.3
B-18 I.F A.1.21 B-43 I. A A.2.1 B-68 I.B A.3.3
B-19 I. A A.1.22 B-44 I.B A.2.1 B-69 I.C A.3.3
B-20 I.B A.1.22 B-45 I.C A.2.1 B-70 I.D A.3.3
B-21 I.C A.1.22 B-46 I.D A.2.1 B-71 I.E A.3.3
B-22 I.D A.1.22 B-47 I.E A.2.1 B-72 I.F A.3.3
B-23 I.E A.1.22 B-48 I.F A.2.1 B-73 I. A A.3.4
B-24 I.F A.1.22 B-49 I. A A.2.2 B-74 I.B A.3.4
B-25 I. A A.1.26 B-50 I.B A.2.2 B-75 I.C A.3.4 compoI II compoI II compoI II sition sition sition
B-76 I.D A.3.4 B-1 15 I. A B.1.8 B-154 I.D D.2.2
B-77 I.E A.3.4 B-1 16 I.B B.1.8 B-155 I.E D.2.2
B-78 I.F A.3.4 B-1 17 I.C B.1.8 B-156 I.F D.2.2
B-79 I. A A.3.5 B-1 18 I.D B.1.8 B-157 I. A E.1 .1
B-80 I.B A.3.5 B-1 19 I.E B.1.8 B-158 I.B E.1 .1
B-81 I.C A.3.5 B-120 I.F B.1.8 B-159 I.C E.1 .1
B-82 I.D A.3.5 B-121 I. A B.2.2 B-160 I.D E.1 .1
B-83 I.E A.3.5 B-122 I.B B.2.2 B-161 I.E E.1 .1
B-84 I.F A.3.5 B-123 I.C B.2.2 B-162 I.F E.1 .1
B-85 I. A A.4.5 B-124 I.D B.2.2 B-163 I. A G.3.1
B-86 I.B A.4.5 B-125 I.E B.2.2 B-164 I.B G.3.1
B-87 I.C A.4.5 B-126 I.F B.2.2 B-165 I.C G.3.1
B-88 I.D A.4.5 B-127 I. A B.2.4 B-166 I.D G.3.1
B-89 I.E A.4.5 B-128 I.B B.2.4 B-167 I.E G.3.1
B-90 I.F A.4.5 B-129 I.C B.2.4 B-168 I.F G.3.1
B-91 I. A A.4.1 1 B-130 I.D B.2.4 B-169 I. A G.3.5
B-92 I.B A.4.1 1 B-131 I.E B.2.4 B-170 I.B G.3.5
B-93 I.C A.4.1 1 B-132 I.F B.2.4 B-171 I.C G.3.5
B-94 I.D A.4.1 1 B-133 I. A B.2.6 B-172 I.D G.3.5
B-95 I.E A.4.1 1 B-134 I.B B.2.6 B-173 I.E G.3.5
B-96 I.F A.4.1 1 B-135 I.C B.2.6 B-174 I.F G.3.5
B-97 I. A B.1.4 B-136 I.D B.2.6 B-175 I. A H.1.2
B-98 I.B B.1.4 B-137 I.E B.2.6 B-176 I.B H.1.2
B-99 I.C B.1.4 B-138 I.F B.2.6 B-177 I.C H.1.2
B-100 I.D B.1.4 B-139 I. A B.3.1 B-178 I.D H.1.2
B-101 I.E B.1.4 B-140 I.B B.3.1 B-179 I.E H.1.2
B-102 I.F B.1.4 B-141 I.C B.3.1 B-180 I.F H.1.2
B-103 I. A B.1.5 B-142 I.D B.3.1 B-181 I. A H.1.4
B-104 I.B B.1.5 B-143 I.E B.3.1 B-182 I.B H.1.4
B-105 I.C B.1.5 B-144 I.F B.3.1 B-183 I.C H.1.4
B-106 I.D B.1.5 B-145 I. A D.1 .2 B-184 I.D H.1.4
B-107 I.E B.1.5 B-146 I.B D.1 .2 B-185 I.E H.1.4
B-108 I.F B.1.5 B-147 I.C D.1 .2 B-186 I.F H.1.4
B-109 I. A B.1.6 B-148 I.D D.1 .2 B-187 I. A H.3.2
B-1 10 I.B B.1.6 B-149 I.E D.1 .2 B-188 I.B H.3.2
B-1 1 1 I.C B.1.6 B-150 I.F D.1.2 B-189 I.C H.3.2
B-1 12 I.D B.1.6 B-151 I. A D.2.2 B-190 I.D H.3.2
B-1 13 I.E B.1.6 B-152 I.B D.2.2 B-191 I.E H.3.2
B-1 14 I.F B.1.6 B-153 I.C D.2.2 B-192 I.F H.3.2 compoI II compoI II compoI II sition sition sition
B-193 I. A H.3.4 B-203 I.E H.4.2 B-213 I.C K.1 .3
B-194 I.B H.3.4 B-204 I.F H.4.2 B-214 I.D K.1 .3
B-195 I.C H.3.4 B-205 I. A H.4.9 B-215 I.E K.1 .3
B-196 I.D H.3.4 B-206 I.B H.4.9 B-216 I.F K.1 .3
B-197 I.E H.3.4 B-207 I.C H.4.9 B-217 I. A K.1 .4
B-198 I.F H.3.4 B-208 I.D H.4.9 B-218 I.B K.1 .4
B-199 I. A H.4.2 B-209 I.E H.4.9 B-219 I.C K.1 .4
B-200 I.B H.4.2 B-210 I.F H.4.9 B-220 I.D K.1 .4
B-201 I.C H.4.2 B-21 1 I. A K.1.3 B-221 I.E K.1 .4
B-202 I.D H.4.2 B-212 I.B K.1.3 B-222 I.F K.1 .4
According to a further preferred embodiment of the invention, component II is selected from the following fungicide compounds: fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), orysastrobin (A.1 .12), pyraclostrobin (A.1.14), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), isopyrazam (A.3.12), meptyldinocap (A.4.6), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1.12), ipconazole (B.1.15), metconazole (B.1.17),
myclobutanil (B.1 .18), imazalil (B.1 .44), kiralaxyl (C.1 .3), metalaxyl (C.1.4), mefenoxam (C.1.5), hymexazole (C.2.1 ), fluopicolide (D.2.4), metrafenone (D.2.6), mepanipyrim (E.1 .2), iprodione (F.1.2), fludioxonil (F.1.5), mandipropamid (G.3.3), iprovalicarb (G.3.6), mancozeb (H.2.2), metiram (H.2.5), folpet (H.3.5), guazatine (H.4.4), fosetyl-AI (J.1.7), proquinazid (K.1 .23).
Consequently, further particularly preferred two-component compositions are compiled in Table B1 , wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B1 : Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
compoI II compoI II compoI II sition sition sition
B1-1 I. A A.1.8 B1-9 I.C A.1.9 B1-17 I.E A.1 .12
B1-2 I.B A.1.8 B1-10 I.D A.1.9 B1-18 I.F A.1 .12
B1-3 I.C A.1.8 B1-1 1 I.E A.1.9 B1-19 I. A A.1 .14
B1-4 I.D A.1.8 B1-12 I.F A.1.9 B1-20 I.B A.1 .14
B1-5 I.E A.1.8 B1-13 I. A A.1.12 B1-21 I.C A.1 .14
B1-6 I.F A.1.8 B1-14 I.B A.1.12 B1-22 I.D A.1 .14
B1-7 I. A A.1.9 B1-15 I.C A.1.12 B1-23 I.E A.1 .14
B1-8 I.B A.1.9 B1-16 I.D A.1.12 B1-24 I.F A.1 .14 compoI II compoI II compoI II sition sition sition
B1-25 I. A A.3.7 B1-64 I.D B.1.11 B1-103 I. A C.1.4
B1-26 I.B A.3.7 B1-65 I.E B.1.11 B1-104 I.B C.1.4
B1-27 I.C A.3.7 B1-66 I.F B.1.11 B1-105 I.C C.1.4
B1-28 I.D A.3.7 B1-67 I. A B.1.12 B1-106 I.D C.1.4
B1-29 I.E A.3.7 B1-68 I.B B.1.12 B1-107 I.E C.1.4
B1-30 I.F A.3.7 B1-69 I.C B.1.12 B1-108 I.F C.1.4
B1-31 I. A A.3.8 B1-70 I.D B.1.12 B1-109 I. A C.1.5
B1-32 I.B A.3.8 B1-71 I.E B.1.12 B1-110 I.B C.1.5
B1-33 I.C A.3.8 B1-72 I.F B.1.12 B1-111 I.C C.1.5
B1-34 I.D A.3.8 B1-73 I. A B.1.15 B1-112 I.D C.1.5
B1-35 I.E A.3.8 B1-74 I.B B.1.15 B1-113 I.E C.1.5
B1-36 I.F A.3.8 B1-75 I.C B.1.15 B1-114 I.F C.1.5
B1-37 I. A A.3.9 B1-76 I.D B.1.15 B1-115 I. A C.2.1
B1-38 I.B A.3.9 B1-77 I.E B.1.15 B1-116 I.B C.2.1
B1-39 I.C A.3.9 B1-78 I.F B.1.15 B1-117 I.C C.2.1
B1-40 I.D A.3.9 B1-79 I. A B.1.17 B1-118 I.D C.2.1
B1-41 I.E A.3.9 B1-80 I.B B.1.17 B1-119 I.E C.2.1
B1-42 I.F A.3.9 B1-81 I.C B.1.17 B1-120 I.F C.2.1
B1-43 I. A A.3.12 B1-82 I.D B.1.17 B1-121 I. A D.2.4
B1-44 I.B A.3.12 B1-83 I.E B.1.17 B1-122 I.B D.2.4
B1-45 I.C A.3.12 B1-84 I.F B.1.17 B1-123 I.C D.2.4
B1-46 I.D A.3.12 B1-85 I. A B.1.18 B1-124 I.D D.2.4
B1-47 I.E A.3.12 B1-86 I.B B.1.18 B1-125 I.E D.2.4
B1-48 I.F A.3.12 B1-87 I.C B.1.18 B1-126 I.F D.2.4
B1-49 I. A A.4.6 B1-88 I.D B.1.18 B1-127 I. A D.2.6
B1-50 I.B A.4.6 B1-89 I.E B.1.18 B1-128 I.B D.2.6
B1-51 I.C A.4.6 B1-90 I.F B.1.18 B1-129 I.C D.2.6
B1-52 I.D A.4.6 B1-91 I. A B.1.44 B1-130 I.D D.2.6
B1-53 I.E A.4.6 B1-92 I.B B.1.44 B1-131 I.E D.2.6
B1-54 I.F A.4.6 B1-93 I.C B.1.44 B1-132 I.F D.2.6
B1-55 I. A B.1.10 B1-94 I.D B.1.44 B1-133 I. A E.1.2
B1-56 I.B B.1.10 B1-95 I.E B.1.44 B1-134 I.B E.1.2
B1-57 I.C B.1.10 B1-96 I.F B.1.44 B1-135 I.C E.1.2
B1-58 I.D B.1.10 B1-97 I. A C.1.3 B1-136 I.D E.1.2
B1-59 I.E B.1.10 B1-98 I.B C.1.3 B1-137 I.E E.1.2
B1-60 I.F B.1.10 B1-99 I.C C.1.3 B1-138 I.F E.1.2
B1-61 I. A B.1.11 B1-100 I.D C.1.3 B1-139 I. A F.1.2
B1-62 I.B B.1.11 B1-101 I.E C.1.3 B1-140 I.B F.1.2
B1-63 I.C B.1.11 B1-102 I.F C.1.3 B1-141 I.C F.1.2 compoI II compoI II compoI II sition sition sition
B1 -142 I.D F.1 .2 B1-161 I.E G.3.6 B1-180 I.F H.3.5
B1 -143 I.E F.1 .2 B1-162 I.F G.3.6 B1-181 I. A H.4.4
B1 -144 I.F F.1 .2 B1-163 I. A H.2.2 B1-182 I.B H.4.4
B1 -145 I. A F.1 .5 B1-164 I.B H.2.2 B1-183 I.C H.4.4
B1 -146 I.B F.1 .5 B1-165 I.C H.2.2 B1-184 I.D H.4.4
B1 -147 I.C F.1 .5 B1-166 I.D H.2.2 B1-185 I.E H.4.4
B1 -148 I.D F.1 .5 B1-167 I.E H.2.2 B1-186 I.F H.4.4
B1 -149 I.E F.1 .5 B1-168 I.F H.2.2 B1-187 I. A J.1.7
B1 -150 I.F F.1 .5 B1-169 I. A H.2.5 B1-188 I.B J.1.7
B1 -151 I. A G.3.3 B1-170 I.B H.2.5 B1-189 I.C J.1.7
B1 -152 I.B G.3.3 B1-171 I.C H.2.5 B1-190 I.D J.1.7
B1 -153 I.C G.3.3 B1-172 I.D H.2.5 B1-191 I.E J.1.7
B1 -154 I.D G.3.3 B1-173 I.E H.2.5 B1-192 I.F J.1.7
B1 -155 I.E G.3.3 B1-174 I.F H.2.5 B1-193 I. A K.1 .23
B1 -156 I.F G.3.3 B1-175 I. A H.3.5 B1-194 I.B K.1 .23
B1 -157 I. A G.3.6 B1-176 I.B H.3.5 B1-195 I.C K.1 .23
B1 -158 I.B G.3.6 B1-177 I.C H.3.5 B1-196 I.D K.1 .23
B1 -159 I.C G.3.6 B1-178 I.D H.3.5 B1-197 I.E K.1 .23
B1 -160 I.D G.3.6 B1-179 I.E H.3.5 B1-198 I.F K.1 .23
According to a further preferred embodiment of the invention, component II is selected from the following fungicide compounds: picoxystrobin (A.1 .13), trifloxystrobin (A.1 .17), penflufen (A.3.15), penthiopyrad (A.3.16), sedaxane (A.3.19), silthiofam (A.4.12), penconazole
(B.1 .21 ), propiconazole (B.1 .22), prothioconazole (B.1 .23), tebuconazole (B.1 .25), tetraconazole (B.1.26), triticonazole (B.1 .29), prochloraz (B.1.46), spiroxamine (B.2.8), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), zoxamide (D.2.5), pyriofenone (D.2.7), pyrimethanil (E.1.3), vinclozolin (F.1 .4), quinoxyfen (F.2.1 ), valifenalate (G.3.7), propamocarb (G.4.1 ), sulfur (H.1 .7), propineb (H.2.6), thiram (H.2.7), ziram (H.2.9), phosporous acid and its salts (J.1 .8), triazoxide (K.1.26).
Consequently, further particularly preferred two-component compositions are compiled in Table B2, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B2: Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients. compoI II compoI II compoI II sition sition sition
B2-1 I. A A.1.13 B2-39 I.C B.1.21 B2-77 I.E B.1 .46
B2-2 I.B A.1.13 B2-40 I.D B.1.21 B2-78 I.F B.1 .46
B2-3 I.C A.1.13 B2-41 I.E B.1.21 B2-79 I. A B.2.8
B2-4 I.D A.1.13 B2-42 I.F B.1.21 B2-80 I.B B.2.8
B2-5 I.E A.1.13 B2-43 I. A B.1.22 B2-81 I.C B.2.8
B2-6 I.F A.1.13 B2-44 I.B B.1.22 B2-82 I.D B.2.8
B2-7 I. A A.1.17 B2-45 I.C B.1.22 B2-83 I.E B.2.8
B2-8 I.B A.1.17 B2-46 I.D B.1.22 B2-84 I.F B.2.8
B2-9 I.C A.1.17 B2-47 I.E B.1.22 B2-85 I. A D.1.4
B2-10 I.D A.1.17 B2-48 I.F B.1.22 B2-86 I.B D.1.4
B2-1 1 I.E A.1.17 B2-49 I. A B.1.23 B2-87 I.C D.1.4
B2-12 I.F A.1.17 B2-50 I.B B.1.23 B2-88 I.D D.1.4
B2-13 I. A A.3.15 B2-51 I.C B.1.23 B2-89 I.E D.1.4
B2-14 I.B A.3.15 B2-52 I.D B.1.23 B2-90 I.F D.1.4
B2-15 I.C A.3.15 B2-53 I.E B.1.23 B2-91 I. A D.1.5
B2-16 I.D A.3.15 B2-54 I.F B.1.23 B2-92 I.B D.1.5
B2-17 I.E A.3.15 B2-55 I. A B.1.25 B2-93 I.C D.1.5
B2-18 I.F A.3.15 B2-56 I.B B.1.25 B2-94 I.D D.1.5
B2-19 I. A A.3.16 B2-57 I.C B.1.25 B2-95 I.E D.1.5
B2-20 I.B A.3.16 B2-58 I.D B.1.25 B2-96 I.F D.1.5
B2-21 I.C A.3.16 B2-59 I.E B.1.25 B2-97 I. A D.2.5
B2-22 I.D A.3.16 B2-60 I.F B.1.25 B2-98 I.B D.2.5
B2-23 I.E A.3.16 B2-61 I. A B.1.26 B2-99 I.C D.2.5
B2-24 I.F A.3.16 B2-62 I.B B.1.26 B2-100 I.D D.2.5
B2-25 I. A A.3.19 B2-63 I.C B.1.26 B2-101 I.E D.2.5
B2-26 I.B A.3.19 B2-64 I.D B.1.26 B2-102 I.F D.2.5
B2-27 I.C A.3.19 B2-65 I.E B.1.26 B2-103 I. A D.2.7
B2-28 I.D A.3.19 B2-66 I.F B.1.26 B2-104 I.B D.2.7
B2-29 I.E A.3.19 B2-67 I. A B.1.29 B2-105 I.C D.2.7
B2-30 I.F A.3.19 B2-68 I.B B.1.29 B2-106 I.D D.2.7
B2-31 I. A A.4.12 B2-69 I.C B.1.29 B2-107 I.E D.2.7
B2-32 I.B A.4.12 B2-70 I.D B.1.29 B2-108 I.F D.2.7
B2-33 I.C A.4.12 B2-71 I.E B.1.29 B2-109 I. A E.1 .3
B2-34 I.D A.4.12 B2-72 I.F B.1.29 B2-1 10 I.B E.1 .3
B2-35 I.E A.4.12 B2-73 I. A B.1.46 B2-1 1 1 I.C E.1 .3
B2-36 I.F A.4.12 B2-74 I.B B.1.46 B2-1 12 I.D E.1 .3
B2-37 I. A B.1.21 B2-75 I.C B.1.46 B2-1 13 I.E E.1 .3
B2-38 I.B B.1.21 B2-76 I.D B.1.46 B2-1 14 I.F E.1 .3 compoI II compoI II compoI II sition sition sition
B2-1 15 I. A F.1 .4 B2-135 I.C G.4.1 B2-155 I.E H.2.7
B2-1 16 I.B F.1 .4 B2-136 I.D G.4.1 B2-156 I.F H.2.7
B2-1 17 I.C F.1 .4 B2-137 I.E G.4.1 B2-157 I. A H.2.9
B2-1 18 I.D F.1 .4 B2-138 I.F G.4.1 B2-158 I.B H.2.9
B2-1 19 I.E F.1 .4 B2-139 I. A H.1 .7 B2-159 I.C H.2.9
B2-120 I.F F.1 .4 B2-140 I.B H.1 .7 B2-160 I.D H.2.9
B2-121 I. A F.2.1 B2-141 I.C H.1 .7 B2-161 I.E H.2.9
B2-122 I.B F.2.1 B2-142 I.D H.1 .7 B2-162 I.F H.2.9
B2-123 I.C F.2.1 B2-143 I.E H.1 .7 B2-163 I. A J.1.8
B2-124 I.D F.2.1 B2-144 I.F H.1.7 B2-164 I.B J.1.8
B2-125 I.E F.2.1 B2-145 I. A H.2.6 B2-165 I.C J.1.8
B2-126 I.F F.2.1 B2-146 I.B H.2.6 B2-166 I.D J.1.8
B2-127 I. A G.3.7 B2-147 I.C H.2.6 B2-167 I.E J.1.8
B2-128 I.B G.3.7 B2-148 I.D H.2.6 B2-168 I.F J.1.8
B2-129 I.C G.3.7 B2-149 I.E H.2.6 B2-169 I. A K.1 .26
B2-130 I.D G.3.7 B2-150 I.F H.2.6 B2-170 I.B K.1 .26
B2-131 I.E G.3.7 B2-151 I. A H.2.7 B2-171 I.C K.1 .26
B2-132 I.F G.3.7 B2-152 I.B H.2.7 B2-172 I.D K.1 .26
B2-133 I. A G.4.1 B2-153 I.C H.2.7 B2-173 I.E K.1 .26
B2-134 I.B G.4.1 B2-154 I.D H.2.7 B2-174 I.F K.1 .26
According to still a further preferred embodiment of the invention, component II is selected from the following fungicide compounds: Bordeaux mixture (H.1.1 ), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), maneb (H.2.3), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10). Consequently, further particularly preferred two-component compositions are compiled in Table B2a, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B2a: Two-component compositions comprising one component I and one component II, in particular binary compositions containing the respective component I and II as only active ingredients.
compoI II compoI II compoI II sition sition sition
B2a-1 I. A H.1 .1 B2a-4 I.D H.1 .1 B2a-7 I. A H.1 .5
B2a-2 I.B H.1 .1 B2a-5 I.E H.1 .1 B2a-8 I.B H.1 .5
B2a-3 I.C H.1 .1 B2a-6 I.F H.1 .1 B2a-9 I.C H.1 .5 compoI II compoI II compoI II sition sition sition
B2a-10 I.D H.1 .5 B2a-17 I.E H.1 .6 B2a-24 I.F H.2.3
B2a-1 1 I.E H.1 .5 B2a-18 I.F H.1 .6 B2a-25 I. A H.4.10
B2a-12 I.F H.1 .5 B2a-19 I. A H.2.3 B2a-26 I.B H.4.10
B2a-13 I. A H.1 .6 B2a-20 I.B H.2.3 B2a-27 I.C H.4.10
B2a-14 I.B H.1 .6 B2a-21 I.C H.2.3 B2a-28 I.D H.4.10
B2a-15 I.C H.1 .6 B2a-22 I.D H.2.3 B2a-29 I.E H.4.10
B2a-16 I.D H.1 .6 B2a-23 I.E H.2.3 B2a-30 I.F H.4.10
As detailed above, the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ration (S):(R).
According to particular embodiments of the invention, the respective component I is present as (S) enantiomer.
According to a further particular embodiments of the invention, the respective component I is present as (R) enantiomer.
According to a further embodiment, component II is selected from the following fungicides: azoxystrobin (A.1.1 ), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), pyraclostrobin (A.1.14), trifloxystrobin (A.1.17), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), fluxapyroxad (A.3.9), isopyrazam (A.3.12), penthiopyrad (A.3.16), fluazinam (A.4.5), difenoconazole (B.1.5), epoxiconazole (B.1.8), flusilazole (B.1 .1 1 ), metconazole (B.1 .17), propiconazole (B.1 .22), prothioconazole (B.1 .23), tebuconazole (B.1.25), prochloraz (B.1 .46), fenpropimorph (B.2.4), spiroxamine (B.2.8), carbendazim (D.1 .2), metrafenone (D.2.6), cyprodinil (E.1.1 ), sulfur (H.1.7), chlorothalonil (H.3.2), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)- tetraone (H.4.10), fosetyl-AI (J.1.7), phosporous acid and its salts (J.1.8). According to still a further embodiment, component II is selected from the following fungicides: fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), pyraclostrobin (A.1 .14), trifloxystrobin (A.1.17),
benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), fluxapyroxad (A.3.9), penthiopyrad (A.3.16), fluazinam (A.4.5), difenoconazole (B.1.5), epoxiconazole (B.1.8), metconazole
(B.1 .17), propiconazole (B.1.22), prothioconazole (B.1 .23), tebuconazole (B.1 .25), prochloraz (B.1 .46), fenpropimorph (B.2.4), spiroxamine B.2.8), carbendazim (D.1.2), metrafenone (D.2.6), cyprodinil (E.1 .1 ), sulfur (H.1.7), chlorothalonil (H.3.2), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10), fosetyl-AI (J.1 .7), phosporous acid and its salt (J.1.8). According to a further preferred embodiment of the invention, component II is selected from the following growth regulators: mepiquat chloride, chlormequat chloride, trinexapac-ethyl, prohexadione-calcium, ethephon. Consequently, particularly preferred two-component compositions are compiled in Table B3, wherein each row corresponds to one embodiment of the compositions according to the invention. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B3: Two-component compositions comprising one component I and one growth regulator as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
Figure imgf000036_0002
Figure imgf000036_0001
As detailed above, the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R).
According to particular embodiments of the invention, the respective component I is present as (S) enantiomer.
According to a further particular embodiments of the invention, the respective component I is present as (R) enantiomer. According to a further preferred embodiment of the invention, component II is selected from the following herbicides: glyphosate, imazamox, dicamba, glufosinate, imazapic, imazapyr, imazethapyr.
Consequently, particularly preferred two-component compositions are compiled in Table B4, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B4: Two-component compositions comprising one component I and one herbicide as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
Figure imgf000037_0001
Figure imgf000037_0002
As detailed above, the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R).
According to particular embodiments of the invention, the respective component I is present as (S) enantiomer. According to a further particular embodiments of the invention, the respective component I is present as (R) enantiomer.
According to a further preferred embodiment of the invention, component II is selected from the following insecticides: abamectin, acephate, acetamiprid, aldicarb, alpha-cypermethrin, betacyfluthrin, bifenthrin, carbofuran, chlorfenapyr, chlorpyrifos, clothianidin, cyazypyr, cyflumetofen, deltamethrin, dimethoate, dinotefuran, endosulfan, esfenvalerate, fenbutatin oxide, fipronil, flonicamid, flubendiamide, hydramethylnon, imidacloprid, indoxacarb, lambda- cyhalothrin, metaflumizon, methamidophos, metoxyfenozide, nitenpyram, pirimicarb, pymetrozine, pyridabene, rynaxapyr, spirotetramat, spinosad, spinetoram, tebufernpyrad, tefluthrin, terbufos, thiacloprid, thiamethoxam, zetacypermethrin, 1-(1 ,2-dimethyl-propyl)-N- ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.1 ), 1-[1 -(1 - cyano-cyclopropyl)-ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide
(0.27.2), N-ethyl-1-(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide (0.27.3), [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropanecarbonyloxy)- 6,12-dihydroxy-4,6a, 12b-trimethyl-1 1 -oxo-9-(pyridin-3-yl)-1 ,2,3,4,4a,5,6,6a,12a, 12b- decahydro-1 1 H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate (0.28).According to a more specific embodiment thereof, component II is selected from the following insecticides: abamectin, acetamiprid, alpha-cypermethrin, betacyfluthrin, bifenthrin, chlorfenapyr, chlorpyrifos, clothianidin, cyazypyr, cyflumetofen, deltamethrin, dinotefuran, esfenvalerate, fipronil, flonicamid, flubendiamide, imidacloprid, indoxacarb, lambda- cyhalothrin, metaflumizon, metoxyfenozide, nitenpyram, pirimicarb, pymetrozine, pyridabene, rynaxapyr, spirotetramat, spinosad, spinetoram, tebufenpyrad, tefluthrin, thiacloprid, thiamethoxam, zetacypermethrin, 1 -(1 ,2-dimethyl-propyl)-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide (0.27.1 ), 1 -[1-(1-cyano-cyclopropyl)-ethyl]-N-ethyl-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide (0.27.2), N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.3),
[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropanecarbonyloxy)-6,12-dihydroxy- 4,6a,12b-trimethyl-1 1 -oxo-9-(pyridin-3-yl)-1 ,2,3,4,4a,5,6,6a,12a,12b-decahydro-1 1 H,12H- benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate (0.28).
Consequently, particularly preferred two-component compositions are compiled in Table B5, wherein each row corresponds to one embodiment of the compositions according to the invention, i.e. one specific individualized composition. According to one specific aspect, these are binary compositions which each only contain these two components as the active compounds. Furthermore, also every combination of the compositions individualized in this table represent embodiments of the present invention.
Table B5: Two-component compositions comprising one component I and one insecticide as component II, in particular binary compositions containing the respective component I and II as only active ingredients.
compoI II compoI II
sition sition
B5-1 I. A abamectin B5-3 I.C abamectin
B5-2 I.B abamectin B5-4 I.D abamectin compoI II compoI II sition sition
B5-5 I.E abamectin B5-39 I.C chlorpyrifos
B5-6 I.F abamectin B5-40 I.D chlorpyrifos
B5-7 I. A acetamiprid B5-41 I.E chlorpyrifos
B5-8 I.B acetamiprid B5-42 I.F chlorpyrifos
B5-9 I.C acetamiprid B5-43 I. A clothianidin
B5-10 I.D acetamiprid B5-44 I.B clothianidin
B5-1 1 I.E acetamiprid B5-45 I.C clothianidin
B5-12 I.F acetamiprid B5-46 I.D clothianidin
B5-13 alpha- B5-47 I.E clothianidin
I. A cypermethrin B5-48 I.F clothianidin
B5-14 alpha- B5-49 I. A cyazypyr
I.B cypermethrin B5-50 I.B cyazypyr
B5-15 alpha- B5-51 I.C cyazypyr
I.C cypermethrin B5-52 I.D cyazypyr
B5-16 alpha- B5-53 I.E cyazypyr
I.D cypermethrin B5-54 I.F cyazypyr
B5-17 alpha- B5-55 I. A cyflumetofen
I.E cypermethrin B5-56 I.B cyflumetofen
B5-18 alpha- B5-57 I.C cyflumetofen
I.F cypermethrin B5-58 I.D cyflumetofen
B5-19 I. A betacyfluthrin B5-59 I.E cyflumetofen
B5-20 I.B betacyfluthrin B5-60 I.F cyflumetofen
B5-21 I.C betacyfluthrin B5-61 I. A deltamethrin
B5-22 I.D betacyfluthrin B5-62 I.B deltamethrin
B5-23 I.E betacyfluthrin B5-63 I.C deltamethrin
B5-24 I.F betacyfluthrin B5-64 I.D deltamethrin
B5-25 I. A bifenthrin B5-65 I.E deltamethrin
B5-26 I.B bifenthrin B5-66 I.F deltamethrin
B5-27 I.C bifenthrin B5-67 I. A dinotefuran
B5-28 I.D bifenthrin B5-68 I.B dinotefuran
B5-29 I.E bifenthrin B5-69 I.C dinotefuran
B5-30 I.F bifenthrin B5-70 I.D dinotefuran
B5-31 I. A chlorfenapyr B5-71 I.E dinotefuran
B5-32 I.B chlorfenapyr B5-72 I.F dinotefuran
B5-33 I.C chlorfenapyr B5-73 I. A esfenvalerate
B5-34 I.D chlorfenapyr B5-74 I.B esfenvalerate
B5-35 I.E chlorfenapyr B5-75 I.C esfenvalerate
B5-36 I.F chlorfenapyr B5-76 I.D esfenvalerate
B5-37 I. A chlorpyrifos B5-77 I.E esfenvalerate
B5-38 I.B chlorpyrifos B5-78 I.F esfenvalerate compoI II compoII sition sition
B5-79 I. A fipronil B5-1 1 1 lambda-
B5-80 I.B fipronil I.C cyhalothrin
B5-81 I.C fipronil B5-1 12 lambda-
B5-82 I.D fipronil I.D cyhalothrin
B5-83 I.E fipronil B5-1 13 lambda-
B5-84 I.F fipronil I.E cyhalothrin
B5-85 I. A flonicamid B5-1 14 lambda-
B5-86 I.B flonicamid I.F cyhalothrin
B5-87 I.C flonicamid B5-1 15 I. A metaflumizon
B5-88 I.D flonicamid B5-1 16 I.B metaflumizon
B5-89 I.E flonicamid B5-1 17 I.C metaflumizon
B5-90 I.F flonicamid B5-1 18 I.D metaflumizon
B5-91 fluben- B5-1 19 I.E metaflumizon
I. A diamide B5-120 I.F metaflumizon
B5-92 fluben- B5-121 metoxy-
I.B diamide I. A fenozide
B5-93 fluben- B5-122 metoxy-
I.C diamide I.B fenozide
B5-94 fluben- B5-123 metoxy-
I.D diamide I.C fenozide
B5-95 fluben- B5-124 metoxy-
I.E diamide I.D fenozide
B5-96 fluben- B5-125 metoxy-
I.F diamide I.E fenozide
B5-97 I. A imidacloprid B5-126 metoxy-
B5-98 I.B imidacloprid I.F fenozide
B5-99 I.C imidacloprid B5-127 I. A nitenpyram
B5-100 I.D imidacloprid B5-128 I.B nitenpyram
B5-101 I.E imidacloprid B5-129 I.C nitenpyram
B5-102 I.F imidacloprid B5-130 I.D nitenpyram
B5-103 I. A indoxacarb B5-131 I.E nitenpyram
B5-104 I.B indoxacarb B5-132 I.F nitenpyram
B5-105 I.C indoxacarb B5-133 I. A pirimicarb
B5-106 I.D indoxacarb B5-134 I.B pirimicarb
B5-107 I.E indoxacarb B5-135 I.C pirimicarb
B5-108 I.F indoxacarb B5-136 I.D pirimicarb
B5-109 lambda- B5-137 I.E pirimicarb
I. A cyhalothrin B5-138 I.F pirimicarb
B5-1 10 lambda- B5-139 I. A pymetrozine
I.B cyhalothrin B5-140 I.B pymetrozine compoI II compoI II sition sition
B5-141 I.C pymetrozine B5-181 I. A tefluthrin
B5-142 I.D pymetrozine B5-182 I.B tefluthrin
B5-143 I.E pymetrozine B5-183 I.C tefluthrin
B5-144 I.F pymetrozine B5-184 I.D tefluthrin
B5-145 I. A pyridabene B5-185 I.E tefluthrin
B5-146 I.B pyridabene B5-186 I.F tefluthrin
B5-147 I.C pyridabene B5-187 I. A thiacloprid
B5-148 I.D pyridabene B5-188 I.B thiacloprid
B5-149 I.E pyridabene B5-189 I.C thiacloprid
B5-150 I.F pyridabene B5-190 I.D thiacloprid
B5-151 I. A rynaxapyr B5-191 I.E thiacloprid
B5-152 I.B rynaxapyr B5-192 I.F thiacloprid
B5-153 I.C rynaxapyr B5-193 thia-
B5-154 I.D rynaxapyr I. A methoxam
B5-155 I.E rynaxapyr B5-194 thia-
B5-156 I.F rynaxapyr I.B methoxam
B5-157 I. A spirotetramat B5-195 thia-
B5-158 I.B spirotetramat I.C methoxam
B5-159 I.C spirotetramat B5-196 thia-
B5-160 I.D spirotetramat I.D methoxam
B5-161 I.E spirotetramat B5-197 thia-
B5-162 I.F spirotetramat I.E methoxam
B5-163 I. A spinosad B5-198 thia-
B5-164 I.B spinosad I.F methoxam
B5-165 I.C spinosad B5-199 zeta-
B5-166 I.D spinosad I. A cypermethrin
B5-167 I.E spinosad B5-200 zeta-
B5-168 I.F spinosad I.B cypermethrin
B5-169 I. A spinetoram B5-201 zeta-
B5-170 I.B spinetoram I.C cypermethrin
B5-171 I.C spinetoram B5-202 zeta-
B5-172 I.D spinetoram I.D cypermethrin
B5-173 B5-203 zeta-
I.E spinetoram
B5-174 I.E cypermethrin
I.F spinetoram
B5-204 zeta-
B5-175 I. A tebufenpyrad
I.F cypermethrin
B5-176 I.B tebufenpyrad
B5-205 I. A 0.27.1
B5-177 I.C tebufenpyrad
B5-206 I.B 0.27.1
B5-178 I.D tebufenpyrad
B5-207 I.C 0.27.1
B5-179 I.E tebufenpyrad
B5-208 I.D 0.27.1
B5-180 I.F tebufenpyrad compoI II compoI II
sition sition
B5-209 I.E 0.27.1 B5-219 I.C 0.27.3
B5-210 I.F 0.27.1 B5-220 I.D 0.27.3
B5-21 1 I. A 0.27.2 B5-221 I.E 0.27.3
B5-212 I.B 0.27.2 B5-222 I.F 0.27.3
B5-213 I.C 0.27.2 B5-223 I. A 0.28
B5-214 I.D 0.27.2 B5-224 I.B 0.28
B5-215 I.E 0.27.2 B5-225 I.C 0.28
B5-216 I.F 0.27.2 B5-226 I.D 0.28
B5-217 I. A 0.27.3 B5-227 I.E 0.28
B5-218 I.B 0.27.3 B5-228 I.F 0.28
As detailed above, the components I contain chirality centers and may, therefore, be present as racemic mixtures, as pure enantiomers or in the two enantiomers of one component I may be present in any ratio (S):(R). According to particular embodiments of the invention, the respective component I is present as (S) enantiomer.
According to a further particular embodiments of the invention, the respective component I is present as (R) enantiomer.
According to a further aspect, the present invention relates to three-component compositions, i.e. compositions comprising component I, i.e a compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, one component II selected from groups A) to O) and the other component II also selected from groups A) to O), wherein both components II are not identical. In particular, component II in each case is selected from the preferred groups or preferred active compounds as given above for component II.
According to a specific embodiment thereof, exactly three active compounds as defined are present in these compositions (herein also called "ternary compositions"). The composition may, of course, contain any kind of additive or the like as detained below in order to provide a formulation suitable for use in agriculture.
In the inventive three-component-compositions, the weight ratio of component I to the 1 st further active compound II depends on the properties of the active compounds in question and may particularly be 1000:1 to 1 :1000, specifically 500:1 to 1 :500. Preferably, it is in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :20 to 20:1 . It may be preferable for the weight ratio to be in the region of from 1 :10 to 10:1 , preferably from 1 :3 to 3:1 , in particular from 1 :2 to 2:1 . The weight ratio of component I to the 2nd further active compound II may particularly be 1000:1 to 1 :1000, specifically 500:1 to 1 :500. It is preferably in the range of from 1 :100 to 100:1 , preferably in the range of from 1 :50 to 50:1 and in particular in the range of from 1 :20 to 20:1. It may be preferable for the weight ratio to be in the region of from 1 :10 to 10:1 , preferably from 1 :3 to 3:1 , in particular from 1 :2 to 2:1. The weight ratio of 1 st further active compound II to 2nd further active compound II is preferably in the range of from 1 :100 to 100:1 , frequently in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , and in particular in the range of from 1 :10 to 10:1 . It may be preferable for the weight to be in the range of from 1 :3 to 3:1 , in particular from 1 :2 to 2:1.
According to one embodiment, the present invention relates to three-component compositions, comprising a component I, i.e a compound I, in particular a compound selected from
compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailled above, one component II selected from groups groups A) to K) and another component II selected from groups A) to K).
One specific embodiment relates to three-component compositions, wherein component I is as defined above and one component II is selected from group A) of the respiration inhibitors of complex III at Q0 site and the second component II is selected from the group of B) of the sterol biosynthesis inhibitors (SBI fungicides). According to one specific embodiment thereof, one component II is selected from the group of strobilurins. Specifically, component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. According to a further specific embodiment thereof, the second component II is selected from the group of the C14
demethylase inhibitors (DMI fungicides), in particular selected from cyproconazole,
difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole,
myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole and prochloraz. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
A further specific embodiment relates to three-component compositions, wherein component I is as defined above and both components II are selected from the respiration inhibitors of complex III at Qo site, wherein components II are not the same. In particular, both components II are selected from the group of the strobilurins. Specifically, components II are selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. According to a specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
Still a further specific embodiment relates to three-component compositions, wherein component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides) and the second component II is selected from the respiration inhibitors of complex II. According to one specific embodiment thereof, one component II is selected from the group of the C14 demethylase inhibitors (DMI fungicides), in particular selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole and prochloraz. According to a further specific embodiment, the second component II is selected from the group of the carboxamides, in particular selected from benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethyl- indan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)- pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3- (trifluoromethyl)-l ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoro- methyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide and 1 ,3,5-trimethyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, in particular selected from benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad and sedaxane. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II. Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected the respiration inhibitors of complex III at Q0 site and the second component II is selected from the respiration inhibitors of complex II. In particular, the first component II is selected from the group of the strobilurins. Specifically, the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. According to a further specific embodiment, the second component II is selected from the group of the carboxamides, in particular selected from benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluz- amide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4- carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole- 4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 3-(trifluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5- dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide and 1 ,3,5-trimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, in particular selected from benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad and sedaxane. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected from the respiration inhibitors of complex III at Q0 site and the second component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular Delta 14-reductase inhibitors. In a specific embodiment, the first component II is selected from the group of the strobilurins. Specifically, component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim- methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. In a further specific embodiment, the second component II is fenpropimorph. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected the respiration inhibitors of complex III at Q0 site and the second component II is selected from the inhibitors of cell division and cytoskeleton. In a specific embodiment, one component II is selected from the group of the strobilurins. Specifically, the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. In a further specific embodiment, the second component II is selected from tubulin inhibitors such as carbendazim. In a further specific embodiment, the second component II is selected from sell division inhibitors such as tubulin inhibitors such as metrafenone. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected from the respiration inhibitors of complex III at Q0 site and the second component II is selected from the inhibitors with Multi Site Action. In a specific embodiment, the first component II is selected from the group of
strobilurins. Specifically, the first component II is selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. In a further specific embodiment, the second component II is selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone, in particular captan, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, (tri)basic copper sulfate, mancozeb, maneb, metiram, folpet, chlorothalonil, dithianon, dodine and 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone. In one particular embodiment, the second component II in said compositions is chlorothalonil. According to a further specific embodiment, these are ternary compositions which, as active compounds, comprise in each case only the mentioned three active components I, II and II.
Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular from the C14 demethylase inhibitors (DMI fungicides), and the second component II is selected from the inhibitors with Multi Site Action. In a specific embodiment, the first component II is selected from cyproconazole, fluquinconazole,
metconazole, propiconazole and prothioconazole. One particularly suitable component II is fluquinconazole. The second component II is specifically selected from captan, Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, (tri)basic copper sulfate, mancozeb, maneb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone, in particular captan, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, (tri)basic copper sulfate, mancozeb, maneb, metiram, folpet, chlorothalonil, dithianon, dodine and 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone.
Still a further specific embodiment relates to three-component compositions, wherein
component I is as defined above, one component II is selected from the sterol biosynthesis inhibitors (SBI fungicides), in particular from the C14 demethylase inhibitors (DMI fungicides), and the second component II is selected from the signal transduction inhibitors. In a specific embodiment, the first component II is triticonazole and the second component II is fludioxonil.
According to one embodiment, the present invention relates to three-component compositions, comprising a component I, in particular a compound selected from compounds I .A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detailed above, one component II selected from groups groups A) to K) and a second component II selected from groups A) to K).
According to a particular embodiment of the inventive three-component compositions comprising three fungicides, the composition comprises compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.Eand I.F as component I, fluxapyroxad as component II and pyraclostrobin or fenpropimorph as second component II. In a further specific embodiment of the present invention, the inventive three-component compositions comprise compound I, in particular a compound selected from compounds I.A, I.B, I.C, I.D, I.E and I.F or any group of compounds I detained above, as component I, prothioconazole as component II and fluxapyroxad, bixafen, pyraclostrobin, dimoxystrobin, picoxystrobin, fluoxastrobin, fluopyram or penflufen as second component II.
The compounds of the formula I or compositions comprising said compounds according to the invention and the mixtures comprising said compounds and compositions, respectively, 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 following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota (Basidiomycetes), for example, but not limited to the genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungi imperfect!), for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, for example but not limited to the genus Plasmodiophora; Zygomycetes, for example, but not limited to the genus Rhizopus.
Some of the compounds of the formula I and the compositions according to the invention 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 compounds I and the 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; sweet leaf (also called Stevia); 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, compounds I and compositions thereof, respectively 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 includes 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 compounds I 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://cera-gmc.org/, see GM crop database therein).
The compounds I, and mixtures comprising them, and agrochemical compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A brassicola or brassicae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A solan/ or A alternata), tomatoes (e. g. A so/an/ or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A fotf/c/(anthracnose) on wheat and A horde/ on barley; B/po/ar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicoia) 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; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;
Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchit) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochiioboius
(anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H.
oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C.
gossypii), corn (e. g. C. gramlnlco/a: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.
coccodes. black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicoia (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria o
Neonectria spp.) on fruit trees, vines (e. g. C liriodendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;
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, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),
Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampe/ina: anthracnose); Enty/oma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets {E. betae), vegetables (e. g. E. pis/), such as cucurbits (e. g. E.
cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); 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. so/ani( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F.
brasiliense each causing sudden death syndrome 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); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochiioboius) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseo/ή (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia 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. parasitica), onions (e. g. P. destructor), tobacco {P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum);
Physoderma maydis (brown spots) on corn; 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) and broad- leaved trees (e. g. P. ramorurrr. sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. ha/stediion sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa pp., e. g. on cereals, such as barley and wheat {P. graminis) and sugar beets {P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. hum/71 on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. horde/ (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, P. kuehnii (orange rust) on sugar cane and P. asparagio asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia 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); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rh/zocton/a spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. so/ani (root and stem rot) on soybeans, R. so/ani (sheath blight) on rice or R. cerea/is (Rhizoctonia spring blight) on wheat or barley; Rhizopus sto/on/fer (b\ack mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale;
Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fs/ior S. sclerotiorum); 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 tucker!) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph:
Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (p\um pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
(common bunt or stinking smut) on cereals, such as e. g. T. trftfcf (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phased!) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis. corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
In a preferred embodiment the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to 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 Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Hum/cola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as
Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting. The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical
Monograph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, such as described by Mollet and
Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
The binary or ternary mixtures of active compounds described herein can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given herein for the compositions of compounds I.
Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g.
lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid
alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I and 1-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce
spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g.
hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1-50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), 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 usually employed. 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%, in the ready-to-use preparations.
Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting. When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg 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 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) 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 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, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, 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.
A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the
agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
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 or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.
Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more than simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, 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.
When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
In the binary mixtures and compositions according to the invention the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often 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 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1 .
According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
In the ternary mixtures, i.e. compositions according to the invention comprising the component 1 ) and component 2) and a further compound II (component 3), the weight ratio of component 1 ) and component 2) depends from the properties of the active substances 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 in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) 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 in particular in the range of from 1 :4 to 4:1.
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1 ).
These ratios are also suitable for inventive mixtures applied by seed treatment. Experimental Part
The fungicidal action of the mixtures according to the invention can be shown by the tests described 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 may be 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 - x »y/100
E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b
x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a
y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b.
Microtest
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.

Claims

Claims:
1. A fungicidal mixture comprising, as active components,
2) at least one tria
Figure imgf000059_0001
wherein
R1 is hydrogen, chlorine, methyl, difluoromethyl or SF5:
R2 is hydrogen or chlorine;
R3 is hydrogen, chlorine or trifuoromethyl;
R4 is hydrogen, chlorine or trifluoromethyl, or an N-oxide, or an agriculturally useful salt thereof;
and
2) at least one active compound II, selected from groups A) to O):
A) Respiration inhibitors
- Inhibitors of complex III at Q0 site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1.12), picoxystrobin (A.1 .13), pyraclostrobin (A.1 .14),
pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3- (2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- N-methyl-acetamide (A.1 .18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1.21 ), fenamidone (A.1 .22), methyl-/V-[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.23), 1-[3- chloro-2-[[1 -(4-chlorophenyl)-1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5- one (A.1 .24), 1 -[3-bromo-2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4- methyl-tetrazol-5-one (A.1 .25), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3- methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.26), 1-[2-[[1 -(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.27), 1-[2-[[1-(2,4- dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1 .28), 1 -[3-cyclopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy}- methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .30), 1 -[3-(difluoromethoxy)-2-[[2-methyl- 4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .31 ), 1 - methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phen- oxy]methyl]phenyl]tetrazol-5-one (A.1 .32), (Z,2£)-5-[1-(2,4-dichlorophenyl)pyrazol-3- yl]-oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.34), (Z2£)-5-[1-(4- chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enarnide (A.1 .35), pyriminostrobin (A.1 .36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl- oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1 .38);
- inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl- 4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);
- inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), 3-(difluoromethyl)-1-methyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 3-(trifluoromethyl)-1 - methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 1 ,3-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)-
1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1 ,3,5- trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.26), 3- (difluoromethyl)-l ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1-methyl-pyrazole- 4-carboxamide (A.3.28), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-5- fluoro-1 ,3-dimethyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2- methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), N-[(5-chloro-2- isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl- pyrazole-4-carboxamide (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4- yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan- 4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl- indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 - dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 - dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N- [(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2- (difluoromethyl)-N-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3- carboxamide (A.3.39);
- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
Sterol biosynthesis inhibitors (SBI fungicides)
- C14 demethylase inhibitors: triazoles: azaconazole (B.1 .1 ), bitertanol (B.1.2), bromuconazole (B.1 .3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1 .14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1 .21 ), propiconazole (B.1.22), prothioconazole (B.1 .23), simeconazole (B.1 .24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1 .27), triadimenol (B.1 .28), triticonazole (B.1.29), uniconazole (B.1.30), ipfentrifluconazole, (B.1 .37), mefentrifluconazole (B.1 .38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1 ,2,4- triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1 .45), prochloraz (B.1.46), triflumizol (B.1 .47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2- fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);
- Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph- acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );
- Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );
C) Nucleic acid synthesis inhibitors
- phenylamides or acyl amino acid fungicides: benalaxyl (C.1 .1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1.6), oxadixyl (C.1 .7);
- other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
D) Inhibitors of cell division and cytoskeleton
- tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6- methyl-5-phenyl-pyridazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine (D.1 .7), N-ethyl-2-[(3-ethynyl-8-methyl-6- quinolyl)oxy]butanamide (D.1 .8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2- methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2- fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-flu- oroethyl)-2-methoxy-acetamide (D.1.1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N- propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N- propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl- N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2- fluoroethyl)-2-methylsulfanyl-acetamide (D.1 .15), 4-(2-bromo-4-fluoro-phenyl)-N-(2- chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16);
- other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
E) Inhibitors of amino acid and protein synthesis
- methionine synthesis inhibitors: cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
F) Signal transduction inhibitors
- MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2),
procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);
- G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors
- Phospholipid biosynthesis inhibitors: edifenphos (G.1 .1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
- lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
- compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
- inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1-{[3,5- bis(difluoromethyl-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)- 1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3- chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-
1- yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5- bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1 - yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1 -[2-[5- cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-
2- carboxamide (G.5.7), 4-[1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3- (trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.9), 4-[1 -[2-[3,5-bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3- (trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.1 1 );
H) Inhibitors with Multi Site Action
- inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1.2), copper acetate (H.1 .3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)- tetraone (H.4.10);
I) Cell wall synthesis inhibitors
- inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1 .2);
- melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5);
J) Plant defence inducers
- acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1 .3), tiadinil (J.1 .4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum
(J.1.7), phosphorous acid and its salts (J.1 .8), calcium phosphonate (J.1.1 1 ), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9),
4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);
K) Unknown mode of action
- bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1 .4), dazomet (K.1.5), debacarb (K.1 .6), diclocymet (K.1 .7), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1 .1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1 .13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1.17), methasulfocarb (K.1.18), nitrapyrin
(K.1 .19), nitrothal-isopropyl (K.1 .20), tolprocarb (K.1 .21 ), oxin-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1 .24), tecloftalam (K.1.25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methyl formamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]- 1 ,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1 .29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl- formamidine (K.1 .30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3- pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .31 ), N'-[5-bromo-6-(4- isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .32), N'-[5-bromo-2-methyl-6-(1 -phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine (K.1 .34), N'-(5-difluoromethyl-2-methyl-4-(3-tri- methylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro- phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
(pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]- pyridine (K.1 .38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H- benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate
(K.1 .40), picarbutrazox (K.1 .41 ), pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1- methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1 .44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1 .45), quinofumelin (K.1 .47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benz- oxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro- 4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1 .51 ), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), N- methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-/\A [(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide (K.1.54), N-methyl- 4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide (K.1 .55), N-[(E)-methoxy- iminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide (K.1 .56), N-[(Z)- methoxyiminomethyl]-4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]benzamide
(K.1 .57), N-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]cyclopropane- carboxamide (K.1 .58), N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzamide (K.1.59), 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]acetamide (K.1 .60, N-allyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]acetamide (K.1.61 ), N-[(E)-N-methoxy-C-methyl- carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide (K.1.62), N-[(Z)- N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzamide (K.1.63), N-allyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide (K.1.64), 4,4-dimethyl-1 -[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.65), N-methyl-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1.66), 5-methyl-1 - [[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.67);
L) Biopesticides
L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense
activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var.
amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f .
catenulate (also named Giiocladium catenuiatum), Giiocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor a/bus, Paenibacillus alvei, Paenibacillus poiymyxa, Pantoea vagans, Peniciiiium biiaiae, Phiebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia a noma la, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gams/I, T. harmatum, T. harzianum, T. polysporum, T.
stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii,
Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);
L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;
L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp.
kurstaki, B. t. ssp. tenebrionis, Beauveria bass/ana, B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV),
Cryptoph/ebia leucotreta granu\ov\rus (CrleGV), Flavobacterium spp., Helicoverpa nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus
(HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV),
Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acrid um, Nomuraea rileyi, Paecilomyces fumosoroseus, P. niacin us, Paenibacillus popilliae, Pasteur/a spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei,
Streptomyces ga/bus, S. micro flavus,
L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1 -yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,1 1 ,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1 - butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1 -ol, (E,Z)- 2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,1 1-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-
1-yl acetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1 -yl acetate, Z-1 1-tetradecenal, Z-1 1-tetradecen-1 -ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;
L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum amazonense, A. brasilense,
A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropic/, Sinorhizobium meliloti,
M) Growth regulators
abscisic acid (M.1 .1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim,
propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4- (4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl- 2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1 ,1 '-bi- phenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45- 3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl- 2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3- yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5- (acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro- 2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'- dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1 ); 5-(acetyloxy)-4- (2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran- 3-one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)- 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 ); 4-(2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6- dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'- chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H- pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4- ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,
chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu ron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac- sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid- 1-methyhethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]^methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl; triafamone; N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine,
chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron,
thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone- ethyl, chlormethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro- 4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4- trifluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452098-92-9),
N tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole- 1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4- trifluoromethyhphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 452099-05-7), N tetrahydro-,furfuryl-3-(2-chloro-6-fluoro-4-trifluoro-,methylphenoxy)-5-methyl-1 H- pyrazole-1 -carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0), 1-methyl-6-trifluoro^methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4- [2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]- 3-methoxy-but-2-enoate (CAS 948893-00-3),
3-[7-chloro-5-fluoro-2-(trifluoromethyl)- 1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS
212754-02-4);
N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone,
flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4- trifluoromethylphenyl^pyrimidine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium,
glufosinate, glufosinate-P, glufosinate-ammonium;
N.8 DHP synthase inhibitors: asulam;
N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam;
carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napropamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, 11.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000068_0001
11.1
II.2
Figure imgf000068_0002
Figure imgf000069_0001
Figure imgf000069_0002
N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3- ylamine (CAS 175899-01 -1 );
N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA- thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4- amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5- fluoropyridine-2-carboxylate (CAS 1390661 -72-9);
N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and
naptalam-sodium;
N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;
O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, azamethiphos, azinphos- ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;
0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans
allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau- fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin
(pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; DDT, methoxychlor;
0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin,
cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; (2E)- 1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; 1-
[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridine; nicotine;
0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;
0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin,
lepimectin, milbemectin;
0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb,
pyriproxyfen;
0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
0.9 Selective homopteran feeding blockers: pymetrozine, flonicamid;
O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;
0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaericus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,
Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient:
chlorfenapyr, DNOC, sulfluramid;
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap
hydrochloride, thiocyclam, thiosultap sodium;
0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron,
diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;
0.17 Moulting disruptors: cyromazine;
0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide,
fufenozide, chromafenozide;
0.19 Octopamin receptor agonists: amitraz;
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon,
acequinocyl, fluacrypyrim;
0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4- cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]- hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[meth- yl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen,
spirotetramat;
0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide,
calcium phosphide, phosphine, zinc phosphide, cyanide;
.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen; 0.26 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-1- (trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, (S)-3- chloro-N1-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3- chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2- dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)- carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2- propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5- amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1 -(3-chloro-2- pyridinyl)-1 H-pyrazole-5-carboxamide; 3-chloro-1 -(3-chloro-2-pyridinyl)-N-[2,4- dichloro-6-[[(1-cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5- carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro- 2-pyridyl)-1 H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1 ,1- dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3- (fluoromethoxy)-l H-pyrazole-5-carboxamide; cyhalodiamide;
insecticidal active compounds of unknown or uncertain mode of action:
afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,
pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 1 1 -(4-chloro- 2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1-en-10- one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3- en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3- (trifluoromethyl)-l H-1 ,2,4-triazole-5-amine, Bacillus firmus, (E/Z)-N-[1-[(6-chloro-3- pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1 -[(6-chloro-5- fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-2,2,2- trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; (E/Z)-N-[1-[(6- bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[1 -(6- chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-2-chloro-N-[1- [(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-N-[1-[(2- chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.); N-[1- [(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide; N-[1 -[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'-isopropyl-acetamidine; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2- methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3- dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethylamino)-N-[2- bromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]- 2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-te- trafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;
N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; N-[3-[[[2- bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl- benzamide; 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)- ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3- fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-
(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-cyano- N-[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phen- yl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl- benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3, 3,3- hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- benzamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5- fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]- 2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-car- boxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N- ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-methyl-N- [4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N,2-dimethyl-N-[4- methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-ethyl-2-methyl-N-[4- methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide; 1-[(6-chloro-3-pyri- dinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1 ,2- a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1-(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl- ethyl)pyrazole-4-carboxamide; 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1 -methyl-propyl)-5- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N,5-di- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -[1-(1-cyanocyclopropyl)ethyl]- N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-methyl-1 -(2-fluoro-1- methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 - (4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N- (1 -methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4- carboxamide; 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; 2- (3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; methyl 2- [[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; N-[(2,2-di- fluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N-(2,2-diflu- oropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )-N-(2-pyrimi- dinylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]- 2-(3-pyridinyl)-2H-indazole-5-carboxamide, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N- ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol- 4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide; N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl- propanamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclo- propyl)methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner;
0.28 [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropanecarbonyloxy)-6,12- dihydroxy-4,6a,12b-tnmethyl-1 1-oxo-9-(pyridin-3-yl)-1 ,2,3,4,4a,5,6,6a,12a,12b- decahydro-1 1 H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl
cyclopropanecarboxylate; a weight ratio of from 100:1 to 1 :100.
A fungicidal mixture comprising as active components
1 ) at least one compound of the formula I
Figure imgf000074_0001
or an N-oxide, or an agriculturally useful salt thereof, and
2) at least one active compound II selected from groups A) to O as defined in claim 1 , and
3) at least one active compound III selected from groups A) to O) as defined in claim 1 , wherein component 3) is not identical with component 2).
The mixture according to claim 2, comprising a compound I and a compound II and a further active compound III in a synergistically effective amount.
The mixture according to any one of claims 2 or 3, comprising a compound I and a compound II in a weight ratio of from 100:1 to 1 :100, and a compound I and compound III in a weight ratio of from 100:1 to 1 :100.
5. The mixture according to claim 4, wherein the total weight of component 2) and component 3) is based on the amount of the solid material (dry matter) of component 2) and 3), respectively.
6. A mixture according to any one of claims 1 to 5, wherein the component 1 ) is at least one active compound I with R2 being hydrogen and either R3 is hydrogen and R4 is
trifluoromethyl or R3 is trifluoromethyl and R4 is hydrogen.
7. A mixture according to any one of claims 1 to 6, wherein the component 1 ) is at least one active compound I with R1 being chlorine.
8. An agrochemical composition, comprising a solvent or solid carrier and a composition
according to any of claims 1 to 7.
9. The agrochemical composition according to claim 8 further comprising seed in an amount of from 1 g to 1000 g active components per 100 kg of seed.
10. Use of the mixture as defined in any of the claims 1 to 7, or of an agrochemical composition as defined in claim 7 or 8, for controlling phytopathogenic harmful fungi.
1 1. A method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the compound I and the compound II and the compound III as defined in any one of claims 1 to 7, or of a composition as defined in claim 8 or 9.
12. A method for protection of plant propagation material from pytopathogenic fungi, comprising contacting the plant propagation materials with a mixture as defined in any of claims 1 to 7, or with a composition as defined in claim 8 or 9, in a fungicidal effective amount.
13. A method as claimed in claim 12, wherein a mixture as defined in any of claims 1 to 7, or a composition as defined in claim 8 or 9, is applied in an amount of from 0.01 g to 10 kg per
100 kg of plant propagation material.
14. A method as claimed in any of claims 1 1 to 13, wherein the components of the mixture as defined in any of claims 1 to 7 are applied simultaneously, that is jointly or separately, or in succession.
15. Plant propagation material, comprising a mixture as defined in any of claims 1 to 7, or a composition as defined in claim 8 or 9, in an amount of from 0.01 g to 10 kg per 100 kg of plant propagation material.
16. Plant propagation material as claimed in claim 15, wherein the plant propagation material is seed.
PCT/EP2018/061249 2017-05-05 2018-05-03 Fungicidal mixtures comprising triazole compounds WO2018202737A1 (en)

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WO2022128812A1 (en) 2020-12-17 2022-06-23 Basf Se Spore compositions, production and uses thereof
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CN114835696B (en) * 2022-05-24 2024-03-05 贵州医科大学 Phthalide hydrazide compound and preparation method and application thereof

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