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US20030161896A1 - Fungicidal active substance combinations - Google Patents

Fungicidal active substance combinations Download PDF

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Publication number
US20030161896A1
US20030161896A1 US10/371,770 US37177003A US2003161896A1 US 20030161896 A1 US20030161896 A1 US 20030161896A1 US 37177003 A US37177003 A US 37177003A US 2003161896 A1 US2003161896 A1 US 2003161896A1
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Prior art keywords
phenyl
methyl
active compound
methoxy
methoxyimino
Prior art date
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US10/371,770
Inventor
Astrid Mauler-Machnik
Ulrike Wachendorff-Neumann
Herbert Gayer
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Individual
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Individual
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Priority claimed from DE19939841A external-priority patent/DE19939841A1/en
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Priority to US10/371,770 priority Critical patent/US20030161896A1/en
Publication of US20030161896A1 publication Critical patent/US20030161896A1/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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present application relates to novel active compound combinations comprising, on the one hand, pyrimidine derivatives and, on the other hand, other known fungicidally active compounds and being highly suitable for controlling phytopathogenic fungi.
  • Z represents optionally substituted phenyl
  • A represents heterocyclyl, —COOCH 3 or —CO—NH—CH 3 and
  • the fungicidally activity of the active compound combination according to the invention is considerably higher than the sum of the activities of the individual active compounds. An unforeseeable true synergistic effect is present, and not just an addition of activities.
  • Z represents a group
  • R 1 and R 2 represent, independently of one another, hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine or cyano,
  • X represents fluorine
  • A represents —CO—NH—CH 3
  • [0018] may be preferably mentioned.
  • R 1 represents hydrogen
  • R 2 represents methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano
  • R 1 represents methyl
  • R 2 represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano
  • R 2 represents methyl
  • R 1 represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano
  • the active compounds of the formula (I) are known (cf., for example, DE-A 19 646 407, WO 97-27189 or GB 225 3624).
  • the active compounds which are furthermore present in the combinations according to the invention are also known.
  • the active compounds are described, for example, in The Pesticide Manual, 11th Edition, British Crop Protection Council (BCPC).
  • the active compound combinations according to the invention comprise, in addition to at least one active compound of the formula (I), at least one active compound from among the compounds of groups 1) to 82). Additionally, they may also comprise other fungicidally active additives.
  • the combinations according to the invention comprise the active compound of the formula (I) and the mixing partner in the preferred and particularly preferred mixing ratios given in the table below: Preferred mixing Particularly preferred Mixing partner ratio* mixing ratio* spiroxamin 10:1 to 1:20 5:1 to 1:10 quinoxyfen (DE 795) 10:1 to 1:20 5:1 to 1:10 tebuconazole 10:1 to 1:10 5:1 to 1:5 fenpropidin 10:1 to 1:20 5:1 to 1:10 fenpropimorph 10:1 to 1:20 5:1 to 1:10 (R,S)- and (R,R)- and (S,R)- and 10:1 to 1:10 5:1 to 1:5 (S,S)-N(1
  • the active compound combinations according to the invention have very good fungicidal properties and can be employed in particular for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • extenders that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohe
  • Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and Prussian blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds of the formula (I) and the active compound combinations according to the invention can be present as a mixture with other active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators.
  • Mixing partners for such mixtures are, for example:
  • dichlorophen diclobutrazol, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon,
  • kasugamycin copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
  • tebucanozole tecloftalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole,
  • bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • abamectin abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
  • Bacillus thuringiensis bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,
  • fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
  • imidacloprid iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron, p malathion, mecarbam, mervinphos, mesulphenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
  • parathion A parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
  • vamidothion XMC, xylylcarb, YI 5301/5302, zetamethrin.
  • the active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
  • the active compound concentrations in the use forms can be varied within a relatively wide range. In general, they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
  • active compound In the treatment of the seeds, amounts of active compound of generally from 0.001 to 50 g per kilogram of seed, preferably from 0.01 to 10 g, are required.
  • active compound concentrations of from 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages 20-22, 1967):
  • X is the efficacy, expressed in % of the untreated control, when applying the active compound A at a concentration of m ppm,
  • Y is the efficacy, expressed in % of the untreated control, when applying the active compound B at a concentration of m ppm,
  • E is the expected efficacy, expressed in % of the untreated control, when applying the active compounds A and B at a concentration of m and n ppm,
  • E X + Y - X ⁇ ⁇ N 100 .

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Novel active compound combinations of compounds of the formula (I)
Figure US20030161896A1-20030828-C00001
in which
Z, X and A are each as defined in the description
with known active compounds and their use for controlling phytopathogenic fungi are described.

Description

  • The present application relates to novel active compound combinations comprising, on the one hand, pyrimidine derivatives and, on the other hand, other known fungicidally active compounds and being highly suitable for controlling phytopathogenic fungi. [0001]
  • It is already known that pyrimidine derivatives have fungicidal properties (cf. DE-A-19 646 407). The activity of this substance is good; however, at low application rates it sometimes leaves something to be desired. [0002]
  • Furthermore, it is already known that numerous azole derivatives, aromatic carboxylic acid derivatives, morpholine compounds and other heterocycles can be used for controlling fungi (cf. K. H. Büchel “Pflanzenschutz und Schädlingsbekämpfung” pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag, Stuttgart 1977). However, the activity of the substances in question is not always satisfactory at low application rates.[0003]
  • It has now been found that the novel active compound combinations of compounds of the general formula (I) [0004]
    Figure US20030161896A1-20030828-C00002
  • in which [0005]
  • Z represents optionally substituted phenyl, [0006]
  • X represents halogen and [0007]
  • A represents heterocyclyl, —COOCH[0008] 3 or —CO—NH—CH3 and
  • in each case one compound selected from the list of the compounds below [0009]
    1) spiroxamin
    2) quinoxyfen (DE 795)
    3) tebuconazole
    4) fenpropidin
    5) fenpropimorph
    6) (R,S)- and (R,R)- and (S,R)- and
    (S,S)-N-(1-cyano-1,2-
    dimethylpropyl)-2-(2,4-
    dichlorophenoxy)propionamide
    7) chlorothalonil (DAC 2787)
    8) triadimefon
    9) triadimenol
    10) epoxiconazole
    11) metconazole
    12) fluquinconazole
    13) cyproconazole
    14) penconazole
    15) kresoximmethyl
    16) azoxystrobin
    17) cyprodinil
    18) iminoctadiene triacetate (Befran)
    19) flusilazole (Harvesan)
    20) prochloraz (Sportak)
    21) propiconazole (Desmel)
    22) bitertanol (KWG 0599)
    23) imidacloprid (NTN 33893)
    24) dichlofluanid (Euparen)
    25) tolylfluanid (Euparen M)
    26) metalaxyl (Ridomil)
    27) fenpiclonil
    28) difenoconazole
    29) fludioxonil
    30) carbendazim,benomyl
    31) fuberidazol
    32) imazalil
    33) triazoxide (SAS 9244)
    34) cyfluthrin (Pyrethroid)
    35) guazatine
    36) acibenzolar-S-methyl (Bion)
    37) pencycuron (Monceren)
    38) flutolanil (Moncut)
    39) tricyclazole (Beam)
    40) propineb (Antracol)
    41) procymidone (Sumisclex)
    42) mancozeb
    43) folpet (Phaltan)
    44) dimetomorph
    45) cymoxanil (Curzate)
    46) fosetyl-Al (Aliette)
    47) famoxadone
    48) pyrimethanil
    49) mepanipyrim
    50) iprovalicarb
    51) fenhexamid
    52) carpropamid
    53) fluazinam
    54) captan
    55) chinomethionat (Morestan)
    56) fenamidone (RP 7213)
    57) clothianidin
    58) thiacloprid
    59) diacloden
    60) acetamiprid
    61) MTI 334
    62) sulphur
    63) copper
    64) rovral
    65) ronilan
    66) rabcide
    67) hinosan
    68) coratop
    69) 2-(1-chloro-cyclopropyl)-1-(2-
    chlorophenyl)-3-(5-mercapto-
    1,2,4-triazol-1-yl)-propan-2-ol
    70) 1-(3,5-dimethylisoxazol-4-
    sulfonyl)-2-chloro-6,6-difluoro-
    [1,3]-dioxolo-[4,5f]-
    benzimidazole
    71) 3-{1-[4-(<2-chlorophenoxy>5-
    fluoropyrimid-6-yloxy)-phenyl]-
    1-(methoximino)-methyl}-5,6-
    dihydro-1,4,2-dioxazine
    72) zoxamide
    73) cyamidazosulfamide
    74) silthiopham
    75) trifloxystrobin
    76) N-methyl-2-(methoxyimino)-2-
    [2-([1-(3-trifluoromethyl-
    phenyl)ethoxy]iminomethyl)-
    phenyl]acetamide
    77) 2-[2-([2-phenyl-2-methoxy-
    imino-1-methylethyl]imino-
    oxymethyl)phenyl]-2-methoxy-
    imino-N-methylacetamide
    78) 2-[2-([2-(4-fluorophenyl)-2-
    methoxyimino-1-methylethyl]-
    iminooxymethyl)phenyl]-2-
    methoxyimino-N-methyl-
    acetamide
    79) 2-[4-methoxy-3-(1-methyl-
    ethoxy)-1,4-diazabuta-1,3-
    dienyloxymethyl]phenyl-2-
    methoximino-N-
    methylacetamide
    80) methyl N-(2-[1-(4-chloro-
    phenyl)pyrazol-3-yloxymethyl]-
    phenyl)-N-methoxycarbamate
    81) 2,4-dihydro-5-methoxy-2-
    methyl-4-[2-([([1-(3-trifluoro-
    methylphenyl)ethylidene]-
    amino)oxy]methyl)phenyl]-3H-
    1,2,4-triazol-3-one
    82) picoxystrobin
  • in a mixing ratio of a compound of the formula (I) to in each case one compound of the formulae 1) to 82) of from 20:1 to 1:50 parts by weight have very good fungicidal properties. [0010]
  • Surprisingly, the fungicidally activity of the active compound combination according to the invention is considerably higher than the sum of the activities of the individual active compounds. An unforeseeable true synergistic effect is present, and not just an addition of activities. [0011]
  • Compounds of the formula (I), in which [0012]
  • Z represents a group [0013]
    Figure US20030161896A1-20030828-C00003
  • in which [0014]
  • R[0015] 1 and R2 represent, independently of one another, hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine or cyano,
  • X represents fluorine and [0016]
  • A represents —CO—NH—CH[0017] 3,
  • may be preferably mentioned. [0018]
  • In particular, the compounds of the formula (I), in which [0019]
  • R[0020] 1 represents hydrogen and
  • R[0021] 2 represents methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
  • and compounds of the formula (I), in which [0022]
  • R[0023] 1 represents methyl and
  • R[0024] 2 represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
  • and compounds of the formula (I), in which [0025]
  • R[0026] 2 represents methyl and
  • R[0027] 1 represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
  • may be mentioned specifically. [0028]
  • The active compounds of the formula (I) are known (cf., for example, DE-A 19 646 407, WO 97-27189 or GB 225 3624). [0029]
  • The active compounds which are furthermore present in the combinations according to the invention are also known. The active compounds are described, for example, in The Pesticide Manual, 11th Edition, British Crop Protection Council (BCPC). [0030]
  • The active compound combinations according to the invention comprise, in addition to at least one active compound of the formula (I), at least one active compound from among the compounds of groups 1) to 82). Additionally, they may also comprise other fungicidally active additives. [0031]
  • If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise the active compound of the formula (I) and the mixing partner in the preferred and particularly preferred mixing ratios given in the table below: [0032]
    Preferred
    mixing Particularly preferred
    Mixing partner ratio* mixing ratio*
    spiroxamin 10:1 to 1:20  5:1 to 1:10
    quinoxyfen (DE 795) 10:1 to 1:20  5:1 to 1:10
    tebuconazole 10:1 to 1:10 5:1 to 1:5
    fenpropidin 10:1 to 1:20  5:1 to 1:10
    fenpropimorph 10:1 to 1:20  5:1 to 1:10
    (R,S)- and (R,R)- and (S,R)- and 10:1 to 1:10 5:1 to 1:5
    (S,S)-N(1-cyano-1,2-di-
    methylpropyl)-2-(2,4-di-
    chlorophenoxy)propionamide
    chlorothalonil (DAC 2787)  1:1 to 1:50  1:5 to 1:20
    triadimefon 10:1 to 1:10 5:1 to 1:5
    triadimenol 10:1 to 1:10 5:1 to 1:5
    epoxiconazole 10:1 to 1:10 5:1 to 1:5
    metconazole 10:1 to 1:10 5:1 to 1:5
    fluquinconazole 10:1 to 1:10 5:1 to 1:5
    cyproconazole 10:1 to 1:10 5:1 to 1:5
    penconazole 10:1 to 1:10 5:1 to 1:5
    kresoximmethyl 10:1 to 1:10 5:1 to 1:5
    azoxystrobin 10:1 to 1:10 5:1 to 1:5
    cyprodinil  5:1 to 1:20  1:1 to 1:10
    iminoctadiene triacetate 10:1 to 1:10 5:1 to 1:5
    (Befran)
    flusilazole (Harvesan) 10:1 to 1:10 5:1 to 1:5
    prochloraz (Sportak) 10:1 to 1:10 5:1 to 1:5
    propiconazole (Desmel) 10:1 to 1:10 5:1 to 1:5
    bitertanol 10:1 to 1:10 5:1 to 1:5
    imidacloprid 20:1 to 1:20 10:1 to 1:10
    dichlofluanid (Euparen)  1:1 to 1:50  1:1 to 1:20
    tolylfluanid (Euparen M)  1:1 to 1:50  1:1 to 1:20
    metalaxyl (Ridomil) 10:1 to 1:10 5:1 to 1:5
    fenpiclonil 10:1 to 1:10 5:1 to 1:5
    difenoconazole 10:1 to 1:10 5:1 to 1:5
    fludioxonil 10:1 to 1:10 5:1 to 1:5
    carbendazim,benomyl 10:1 to 1:10 5:1 to 1:5
    fuberidazol 20:1 to 1:10 10:1 to 1:5 
    imazalil 20:1 to 1:10 10:1 to 1:5 
    triazoxide (SAS 9244) 20:1 to 1:10 10:1 to 1:5 
    cyfluthrin (Pyrethroid) 20:1 to 1:20 10:1 to 1:10
    guazatine 10:1 to 1:10 5:1 to 1:5
    acibenzolar-S-methyl (Bion) 50:1 to 1:50 20:1 to 1:10
    pencycuron (Monceren) 10:1 to 1:10 5:1 to 1:5
    flutolanil (Moncut) 10:1 to 1:10 5:1 to 1:5
    tricyclazole (Beam) 10:1 to 1:10 5:1 to 1:5
    propineb (Antracol)  1:1 to 1:50  1:5 to 1:20
    procymidone (Sumisclex) 10:1 to 1:10 5:1 to 1:5
    mancozeb  1:1 to 1:50  1:5 to 1:20
    folpet (Phaltan)  1:1 to 1:50  1:5 to 1:20
    dimetomorph 10:1 to 1:10 5:1 to 1:5
    cymoxanil (Curzate) 10:1 to 1:10 5:1 to 1:5
    fosetyl-al (Aliette) 10:1 to 1:50  1:1 to 1:10
    famoxadone 10:1 to 1:10 5:1 to 1:5
    pyrimethanil  5:1 to 1:20  1:1 to 1:10
    mepanipyrim  5:1 to 1:20  1:1 to 1:10
    iprovalicarb 10:1 to 1:10 5:1 to 1:5
    fenhexamid 10:1 to 1:10 5:1 to 1:5
    carpropamid 10:1 to 1:10 5:1 to 1:5
    fluazinam 10:1 to 1:10 5:1 to 1:5
    captan  5:1 to 1:50  1:1 to 1:20
    chinomethionat (Morestan)  5:1 to 1:50  1:1 to 1:20
    fenamidone (RP 7213) 10:1 to 1:10 5:1 to 1:5
    clothianidin 20:1 to 1:20 10:1 to 1:10
    thiacloprid 20:1 to 1:20 10:1 to 1:10
    diacloden 20:1 to 1:20 10:1 to 1:10
    acetamiprid 20:1 to 1:20 10:1 to 1:10
    MTI 334 20:1 to 1:20 10:1 to 1:10
    sulphur 20:1 to 1:20 10:1 to 1:10
    copper 20:1 to 1:20 10:1 to 1:10
    rovral 10:1 to 1:10 5:1 to 1:5
    ronilan 10:1 to 1:10 5:1 to 1:5
    rabcide 10:1 to 1:10 5:1 to 1:5
    hinosan 10:1 to 1:10 5:1 to 1:5
    coratop 10:1 to 1:10 5:1 to 1:5
    2-(1-chloro-cyclopropyl)-1- 20:1 to 1:5  20:1 to 1:5 
    (2-chlorophenyl)-3-(5-
    mercapto-1,2,4-triazol-1-yl)-
    propan-2-ol
    1-(3,5-dimethylisoxazol-4- 50:1 to 1:10 20:1 to 1:5 
    sulfonyl)-2-chloro-6,6-
    difluoro-[1,3]-dioxolo-
    [4,5f]benzimidazole
    3-{1-[4-(<2-chloro- 10:1 to 1:10 5:1 to 1:5
    phenoxy>5-fluoropyrimid-6-
    yloxy)-phenyl]-1-
    (methoximino)-methyl}-5,6-
    dihydro-1,4,2-dioxazine
    zoxamide 50:1 to 1:10 20:1 to 1:5 
    cyamidazosulfamide 20:1 to 1:5  20:1 to 1:5 
    silthiopham 20:1 to 1:10 20:1 to 1:5 
    trifloxystrobin 10:1 to 1:10 5:1 to 1:5
    N-methyl-2-(methoxyimino)- 10:1 to 1:10 5:1 to 1:5
    2-[2-([1-(3-trifluoromethyl-
    phenyl)ethoxy]iminomethyl)-
    phenyl]acetamide
    2-[2-([2-phenyl-2-methoxy- 10:1 to 1:10 5:1 to 1:5
    imino-1-methylethyl]imino-
    oxymethyl)phenyl]-2-
    methoxyimino-N-
    methylacetamide
    2-[2-([2-(4-fluorophenyl)-2- 10:1 to 1:10 5:1 to 1:5
    methoxyimino-1-methyl-
    ethyl]-iminooxymethyl)-
    phenyl]-2-methoxyimino-N-
    methylacetamide
    2-[4-methoxy-3-(1-methyl- 10:1 to 1:10 5:1 to 1:5
    ethoxy)-1,4-diazabuta-1,3-
    dienyloxymethyl]phenyl-2-
    methoximino-N-methyl-
    acetamide
    methyl N-(2-[1-(4-chloro- 10:1 to 1:10 5:1 to 1:5
    phenyl)pyrazol-3-yloxy-
    methyl]phenyl)-N-methoxy-
    carbamate
    2,4-dihydro-5-methoxy-2- 10:1 to 1:10 5:1 to 1:5
    methyl-4-[2-([([1-(3-trifluoro-
    methylphenyl)ethylidene]-
    amino)oxy]methyl)phenyl]-
    3H-1,2,4-triazol-3-one
    picoxystrobin 10:1 to 1:10 5:1 to 1:5
  • The active compound combinations according to the invention have very good fungicidal properties and can be employed in particular for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. [0033]
  • The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. [0034]
  • The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations. [0035]
  • These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose. [0036]
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils. [0037]
  • It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. [0038]
  • The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. [0039]
  • In the formulations, the active compounds of the formula (I) and the active compound combinations according to the invention can be present as a mixture with other active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators. [0040]
  • Mixing partners for such mixtures are, for example: [0041]
  • Fungicides: [0042]
  • 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide; (E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate; methyl (E)-methoximino-[alpha-(o-tolyloxy)-o-tolyl]-acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, [0043]
  • benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, [0044]
  • calcium polysulphide, captafol, captan, carbendazim, carboxin, quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram, [0045]
  • dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon, [0046]
  • edifenphos, epoxyconazole, ethirimol, etridiazole, [0047]
  • fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox, [0048]
  • guazatine, [0049]
  • hexachlorobenzene, hexaconazole, hymexazol, [0050]
  • imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, isoprothiolane, [0051]
  • kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, [0052]
  • mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulphocarb, methfuroxam, metiram, metsulphovax, myclobutanil, [0053]
  • nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, [0054]
  • ofurace, oxadixyl, oxamocarb, oxycarboxin, [0055]
  • pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, [0056]
  • quintozene (PCNB), [0057]
  • sulphur and sulphur preparations, [0058]
  • tebucanozole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole, [0059]
  • validamycin A, vinclozolin, [0060]
  • zineb, ziram. [0061]
  • Bactericides: [0062]
  • bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. [0063]
  • Insecticides/Acaricides/Nematicides: [0064]
  • abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin, [0065]
  • Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben, [0066]
  • cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, [0067]
  • deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton, [0068]
  • edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos, [0069]
  • fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, [0070]
  • HCH, heptenophos, hexaflumuron, hexythiazox, [0071]
  • imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron, p malathion, mecarbam, mervinphos, mesulphenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin, [0072]
  • naled, NC 184, NI 25, nitenpyram, [0073]
  • omethoate, oxamyl, oxydemethon M, oxydeprofos, [0074]
  • parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, [0075]
  • quinalphos, [0076]
  • RH 5992, [0077]
  • salithion, sebufos, silafluofen, sulphotep, sulprofos, [0078]
  • tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb, [0079]
  • vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin. [0080]
  • The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting. [0081]
  • In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a relatively wide range. In general, they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%. [0082]
  • In the treatment of the seeds, amounts of active compound of generally from 0.001 to 50 g per kilogram of seed, preferably from 0.01 to 10 g, are required. [0083]
  • In the treatment of the soil, active compound concentrations of from 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action. [0084]
  • The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities. [0085]
  • A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually. [0086]
  • The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages 20-22, 1967): [0087]
  • If [0088]
  • X is the efficacy, expressed in % of the untreated control, when applying the active compound A at a concentration of m ppm, [0089]
  • Y is the efficacy, expressed in % of the untreated control, when applying the active compound B at a concentration of m ppm, [0090]
  • E is the expected efficacy, expressed in % of the untreated control, when applying the active compounds A and B at a concentration of m and n ppm, [0091]
  • then [0092] E = X + Y - X   N 100 .
    Figure US20030161896A1-20030828-M00001
  • If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula. [0093]

Claims (5)

1. Active compound combination, comprising a compound of the formula (I)
Figure US20030161896A1-20030828-C00004
in which
Z represents optionally substituted phenyl,
X represents halogen and
A represents heterocyclyl, —COOCH3 or —CO—NH—CH3 and
in each case one of the compounds below
1) spiroxamin 2) quinoxyfen (DE 795) 3) tebuconazole 4) fenpropidin 5) fenpropimorph 6) (R,S)- and (R,R)- and (S,R)- and (S,S)-N-(1-cyano-1,2-dimethyl- propyl)-2-(2,4-dichloro- phenoxy)propionamide 7) chlorothalonil (DAC 2787) 8) triadimefon 9) triadimenol 10) epoxiconazole 11) metconazole 12) fluquinconazole 13) cyproconazole 14) penconazole 15) kresoximmethyl 16) azoxystrobin 17) cyprodinil 18) iminoctadiene triacetate (Befran) 19) flusilazole (Harvesan) 20) prochloraz (Sportak) 21) propiconazole (Desmel) 22) bitertanol (KWG 0599) 23) imidacloprid (NTN 33893) 24) dichlofluanid (Euparen) 25) tolylfluanid (Euparen M) 26) metalaxyl (Ridomil) 27) fenpiclonil 28) difenoconazole 29) fludioxonil 30) carbendazim,benomyl 31) fuberidazol 32) imazalil 33) triazoxide (SAS 9244) 34) cyfluthrin (Pyrethroid) 35) guazatine 36) acibenzolar-S-methyl (Bion) 37) pencycuron (Monceren) 38) flutolanil (Moncut) 39) tricyclazole (Beam) 40) propineb (Antracol) 41) procymidone (Sumisclex) 42) mancozeb 43) folpet (Phaltan) 44) dimetomorph 45) cymoxanil (Curzate) 46) fosetyl-Al (Aliette) 47) famoxadone 48) pyrimethanil 49) mepanipyrim 50) iprovalicarb 51) fenhexamid 52) carpropamid 53) fluazinam 54) captan 55) chinomethionat (Morestan) 56) fenamidone (RP 7213) 57) clothianidin 58) thiacloprid 59) diacloden 60) acetamiprid 61) MTI 334 62) sulphur 63) copper 64) rovral 65) ronilan 66) rabcide 67) hinosan 68) coratop 69) 2-(1-chloro-cyclopropyl)-1-(2- chlorophenyl)-3-(5-mercapto- 1,2,4-triazol-1-yl)-propan-2-ol 70) 1-(3,5-dimethylisoxazol-4- sulfonyl)-2-chloro-6,6-difluoro- [1,3]-dioxolo-[4,5f]- benzimidazole 71) 3-{1-[4-(<2-chlorophenoxy>5- fluoropyrimid-6-yloxy)-phenyl]- 1-(methoximino)-methyl}-5,6- dihydro-1,4,2-dioxazine 72) zoxamide 73) cyamidazosulfamide 74) silthiopham 75) trifloxystrobin 76) N-methyl-2-(methoxyimino)-2- [2-([1-(3-trifluoromethyl- phenyl)ethoxy]iminomethyl)phenyl]acetamide 77) 2-[2-([2-phenyl-2-methoxy- imino-1-methylethyl]imino- oxymethyl)phenyl]-2-methoxy- imino-N-methylacetamide 78) 2-[2-([2-(4-fluorophenyl)-2- methoxyimino-1-methylethyl]- iminooxymethyl)phenyl]-2- methoxyimino-N-methyl- acetamide 79) 2-[4-methoxy-3-(1- methylethoxy)-1,4-diazabuta- 1,3-dienyloxymethyl]phenyl-2- methoximino-N- methylacetamide 80) methyl N-(2-[1-(4-chloro- phenyl)pyrazol-3-yloxy- methyl]phenyl)-N-methoxy- carbamate 81) 2,4-dihydro-5-methoxy-2- methyl-4-[2-([([1-(3- trifluoromethylphenyl)- ethylidene]amino)oxy]methyl)- phenyl]-3H-1,2,4-triazol-3-one 82) picoxystrobin
in a mixing ratio of a compound of the formula (I) to in each case one compound of the formulae 1) to 82) of from 20:1 to 1:50 parts by weight.
2. Composition, characterized in that it comprises an active compound combination as defined in claim 1.
3. Method for controlling fungi, characterized in that active compound combinations as defined in claim 1 or compositions as defined in claim 2 are allowed to act on the fungi and/or on the habitat.
4. Use of active compound combinations as defined in claim 1 for controlling fungi.
5. Process for preparing fungicidal compositions, characterized in that active compound combinations as defined in claim 1 are mixed with extenders and/or surfactants.
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