EP1117654A1 - Sulfonyltriazol derivatives and their use for combating micro-organisms - Google Patents

Sulfonyltriazol derivatives and their use for combating micro-organisms

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Publication number
EP1117654A1
EP1117654A1 EP99946189A EP99946189A EP1117654A1 EP 1117654 A1 EP1117654 A1 EP 1117654A1 EP 99946189 A EP99946189 A EP 99946189A EP 99946189 A EP99946189 A EP 99946189A EP 1117654 A1 EP1117654 A1 EP 1117654A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
sulfonyltriazole
methyl
derivatives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99946189A
Other languages
German (de)
French (fr)
Inventor
Lutz Assmann
Stefan Hillebrand
Klaus Stenzel
Ulrike Wachendorff-Neumann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1117654A1 publication Critical patent/EP1117654A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to new sulfonyltriazole derivatives, a process for their preparation and their use for controlling unwanted microorganisms.
  • R 1 stands for hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy or for optionally substituted heterocyclyl and
  • R 2 represents alkyl or optionally substituted heterocyclyl or a radical of the formula stands in what
  • R 3 represents halogen, alkyl or phenyl
  • R 4 represents hydrogen or alkyl
  • R 5 represents alkyl or optionally substituted phenyl
  • R 4 and R 5 together with the nitrogen atom to which they are attached form a heterocyclic ring which can be substituted and can also contain an additional hetero atom,
  • R 'and shark have the meanings given above. with sulfonic acid halides of the formula
  • R 2 has the meaning given above and
  • the sulfonyltriazole derivatives of the formula (I) have very good microbicidal properties and can be used to combat unwanted microorganisms in crop protection and in agriculture.
  • the sulfonyltriazole derivatives of the formula (I) according to the invention show a significantly better fungicidal activity than 1- (3,5-dimethyl-isoxazole-4-sulfonyl) -1H-benzotriazole, which is a constitutionally similar, previously known active ingredient with the same direction of action.
  • sulfonyltriazole derivatives according to the invention are each defined substances, but their structure cannot always be clearly established. You can use one of the formulas as connections
  • Shark also preferably represents fluorine, chlorine or bromine.
  • R 1 preferably represents hydrogen, alkyl having 1 to 6 carbon atoms
  • R 1 stands for phenoxy, which can be substituted once to three times, in the same way or differently, by halogen, nitro, C j -Cg-alkyl, C j -C ⁇ alkoxy, CC 6 -alkylthio, C Cg-haloalkyl with 1 to 5 same or different halogen atoms, C j -C 6 haloalkoxy with 1 to 5 identical or different halogen atoms, C ⁇ -C 6 haloalkylthio with 1 to 5 identical or different halogen atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms,
  • R 1 represents a heterocyclyl radical with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, where this radical can be monosubstituted to trisubstituted, identically or differently, by halogen, cyano, nitro, amino, Hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4
  • R 2 preferably represents alkyl having 1 to 6 carbon atoms or one
  • R 2 also preferably represents a radical of the formula
  • R 3 preferably represents fluorine, chlorine, bromine, alkyl having 1 to 6 carbon atoms or phenyl.
  • R 4 preferably represents hydrogen or alkyl having 1 to 6 carbon atoms.
  • R 5 preferably represents alkyl having 1 to 6 carbon atoms or phenyl which can be monosubstituted to trisubstituted, identical or different, by halogen, nitro, C r C 6 alkyl, C, -C 6 alkoxy, C r C 6 -Alkylthio, C r C 6 - haloalkyl with 1 to 5 identical or different halogen atoms, C j - C 6 -haloalkoxy with 1 to 5 identical or different halogen atoms,
  • R 4 and R 5 together with the nitrogen atom to which they are attached, preferably also represent a saturated heterocyclic ring
  • ring may contain a further nitrogen or oxygen atom and may be mono- to tetrasubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms.
  • Shark is also particularly preferably fluorine, chlorine or bromine.
  • R 1 particularly preferably represents hydrogen.
  • Alkyl part for cycloalkyl having 3 to 7 carbon atoms or for
  • R l particularly preferably represents phenyl which can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,
  • R 1 particularly preferably represents phenoxy, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl
  • R 1 also particularly preferably represents furyl.
  • Bromine cyano, nitro, amino, hydroxy, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy.
  • R 2 particularly preferably represents methyl, ethyl, n-propyl or isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrazinyl,
  • R 2 also particularly preferably represents a radical of the formula
  • R 3 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or phenyl.
  • R 4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
  • R 5 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, or phenyl which can be monosubstituted to trisubstituted in the same or different manner by Fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,
  • R 4 and R 5 also together with the nitrogen atom to which they are attached are particularly preferably pyrrolidinyl, piperidinyl,
  • Morpholinyl or piperazinyl where each of these residues can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl or tert-butyl .
  • Hal very particularly preferably represents chlorine or bromine.
  • R 1 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, for alkoyalkyl having 1 or 2 carbon atoms in the alkoxy part and 1 or 2 Carbon atoms in the alkyl part, for cyclopropyl, cyclopentyl, cyclohexyl or for alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part,
  • R 1 very particularly preferably represents phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl and / or cyclohexyl
  • R 1 very particularly preferably represents phenoxy, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl and / or cyclohexyl
  • R 1 also very particularly preferably represents furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl,
  • R 2 very particularly preferably represents methyl, ethyl, n-propyl or isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl,
  • Ethoxy trifluoromethyl, difluoromethoxy. Trifluoromethoxy, acetyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl.
  • R 2 also very particularly preferably represents a radical of the formula
  • R 3 very particularly preferably represents fluorine. Chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or phenyl.
  • R 4 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl or n-butyl.
  • R 5 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, or phenyl, which can be monosubstituted to trisubstituted in the same or different manner by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy , Cyano, cyclopropyl, cyclopenty
  • R 4 and R 5 also together with the nitrogen atom to which they are attached very particularly preferably represent pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, where each of these radicals can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, methyl and / or ethyl.
  • Formula (II) provides a general definition of the triazoles required as starting materials when carrying out the process according to the invention.
  • R 1 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • the triazoles of formula (II) can exist in the following three tautomeric forms.
  • Tautomers end products of the formula (I) are obtained in the form of mixtures.
  • the triazoles of the formula (II) are known or can be prepared by known methods (cf. J. Prakt. Chem. 3 T2 (1970), 610-621).
  • Formula (III) provides a general definition of the sulfonic acid halides required as reaction components for carrying out the process according to the invention.
  • R ⁇ preferably has the meaning which has already been given as preferred for R ⁇ in connection with the description of the compounds of the formula (I) according to the invention.
  • Shark 1 is preferably chlorine.
  • the sulfonic acid halides of the formula (III) are known or can be prepared by known processes (cf. J. Heterocyclic Chem. 1981, 997-1006 and EP-A 0 238 824).
  • Suitable diluents for carrying out the process according to the invention are all inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as chlorobenzene.
  • Dichlorobenzene dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1, 2-diethoxyethane or anisole
  • Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • Esters such as methyl acetate or ethyl acetate.
  • Suitable acid binders for carrying out the process according to the invention are all customary inorganic or organic bases.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates are preferably usable.
  • ammonium compounds such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl -benzylamine, pyridine, N-
  • Methylpiperidine N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under atmospheric pressure. It is also possible, however, under increased or reduced pressure
  • the processing takes place according to usual methods.
  • the procedure is such that the reaction mixture is poured into water, the resulting mixture is extracted several times with an organic solvent which is sparingly soluble in water, and the combined organic phases are dried and concentrated under reduced pressure. The remaining residue can, if necessary, be freed from any impurities that may still be present using customary cleaning methods.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention can be used particularly successfully to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Phytophthora species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production plants for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • the preferred technical materials are adhesives, glues, papers and cartons, leather, wood, paints,
  • Cooling lubricants and heat transfer liquids called, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma such as Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorefhylenes 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 sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: for example natural stone powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: e.g.
  • Suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates.
  • Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases you get it synergistic effects, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M,
  • Famoxadone Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimidol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolut.
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovededione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
  • Cadusafos carbaryl, carbofuran, carbophenothione, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos. Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaphorthrin, Cis-Resmethrin, Cispermethrin,
  • Flufenoxuron Flutenzine, Fluvalinate, Fonophos.
  • Fosmethilan Fosthiazate, Fubfenprox, Furathiocarb, Granuloseviren, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivermecfin,
  • Nuclear polyhedron viruses lambda cyhalothrin, lufenuron,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenophos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion,
  • Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Thetacyper- methrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocethriniazine, Tralocethriniazin
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95% by weight, preferably 10 to 75% by weight.
  • the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimal amount can be determined by test series.
  • the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of activity of the active ingredients to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients are used to enlarge the spectrum of activity or Achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • the sulfonyl-triazole derivatives of the formula (I) according to the invention can also be used for the treatment of transgenic plants. In cooperation with the substances formed by expression, synergistic effects can also occur. Manufacturing examples
  • Emulsifier 3 parts by weight of alkyl aryl polyglycol ether
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Abstract

The invention relates to new sulfonyltriazol derivatives of formula (I), in which Hal is fluorine, chlorine or bromine, R<1> is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkyl aminocarbonyl, possibly substituted phenyl, possibly substituted phenoxy or possibly substituted heterocyclyl; R<2> is alkyl or possibly substituted heterocyclyl or a rest of formula in which R<3> (a) is halogen, alkyl or phenyl, R<4> is hydrogen or alkyl and R<5> is alkyl or possibly substituted phenyl; or R<4> and R<5> together with the nitrogen atom to which they are bound form a heterocyclic ring which can be substituted and can further contain an additional heteroatom. The invention further relates to a method for producing the above substances and to their use in combating undesirable micro-organisms.

Description

SULFONYLT IAZOL-DERIVATE UND IHRE VERWENDUNG ZUR BEKÄMPFUNG VON MIKROORGANISMENSULFONYLT IAZOLE DERIVATIVES AND THEIR USE FOR COMBATING MICROORGANISMS
Die vorliegende Erfindung betrifft neue Sulfonyltriazole-Derivate, ein Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von unerwünschten Mikroorganismen.The present invention relates to new sulfonyltriazole derivatives, a process for their preparation and their use for controlling unwanted microorganisms.
Es ist bereits bekannt geworden, dass bestimmte Benzotriazol-Derivate fungizide Eigenschaften besitzen (vgl. DE-A 195 23 446). So läßt sich zum Beispiel l-(3,5- Dimethyl-isoxazol-4-sulfonyl)-lH-benzotriazol zur Bekämpfung von Pilzen ein- setzen. Die Wirksamkeit dieses Stoffes ist gut, läßt aber bei niedrigen Aufwandmengen in manchen Fällen zu wünschen übrig.It has already become known that certain benzotriazole derivatives have fungicidal properties (cf. DE-A 195 23 446). For example, 1- (3,5-dimethyl-isoxazole-4-sulfonyl) -1H-benzotriazole can be used to combat fungi. The effectiveness of this substance is good, but leaves something to be desired in some cases at low application rates.
Es wurden nun neue Sulfonyltriazol-Derivate der FormelThere have now been new sulfonyltriazole derivatives of the formula
in welcher in which
Hai für Fluor, Chlor oder Brom steht,Shark represents fluorine, chlorine or bromine,
R1 für Wasserstoff, Alkyl, Alkoxyalkyl, Cycloalkyl, Alkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy oder für gegebenenfalls substituiertes Heterocyclyl steht undR 1 stands for hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy or for optionally substituted heterocyclyl and
R2 für Alkyl oder für gegebenenfalls substituiertes Heterocyclyl steht oder für einen Rest der Formel steht, worinR 2 represents alkyl or optionally substituted heterocyclyl or a radical of the formula stands in what
R3 für Halogen, Alkyl oder Phenyl steht,R 3 represents halogen, alkyl or phenyl,
R4 für Wasserstoff oder Alkyl steht undR 4 represents hydrogen or alkyl and
R5 für Alkyl oder gegebenenfalls substituiertes Phenyl steht,R 5 represents alkyl or optionally substituted phenyl,
oderor
R4 und R5 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring bilden, der substituiert sein kann und auch ein zusätzliches Heteroatom enthalten kann,R 4 and R 5 together with the nitrogen atom to which they are attached form a heterocyclic ring which can be substituted and can also contain an additional hetero atom,
gefunden.found.
Weiterhin wurde gefunden, dass man Sulfonyltriazol-Derivate der Formel (I) erhält, wenn man Triazole der FormelIt has also been found that sulfonyltriazole derivatives of the formula (I) are obtained if triazoles of the formula
in welcher in which
R' und Hai die oben angegebenen Bedeutungen haben. mit Sulfonsäurehalogeniden der FormelR 'and shark have the meanings given above. with sulfonic acid halides of the formula
R2-Sθ2-Hal' (III) in welcherR 2 -Sθ2-Hal '(III) in which
R2 die oben angegebene Bedeutung hat undR 2 has the meaning given above and
Hai1 für Chlor oder Brom steht,Shark 1 represents chlorine or bromine,
gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Schließlich wurde gefunden, dass die Sulfonyltriazol-Derivate der Formel (I) sehr gute mikrobizide Eigenschaften besitzen und zur Bekämpfung von unerwünschten Mikroorganismen im Pflanzenschutz und in der Landwirtschaft eingesetzt werden können.Finally, it was found that the sulfonyltriazole derivatives of the formula (I) have very good microbicidal properties and can be used to combat unwanted microorganisms in crop protection and in agriculture.
Überraschenderweise zeigen die erfindungsgemäßen Sulfonyltriazol-Dervate der Formel (I) eine wesentlich bessere fungizide Wirksamkeit als l-(3,5-Dimethyl- isoxazol-4-sulfonyl)-lH-benzotriazol, welches ein konstitionell ähnlicher, vorbekannter Wirkstoff gleicher Wirkungsrichtung ist.Surprisingly, the sulfonyltriazole derivatives of the formula (I) according to the invention show a significantly better fungicidal activity than 1- (3,5-dimethyl-isoxazole-4-sulfonyl) -1H-benzotriazole, which is a constitutionally similar, previously known active ingredient with the same direction of action.
Bei den erfindungsgemäßen Sulfonyltriazol-Derivaten handelt es sich jeweils um definierte Substanzen, deren Struktur sich jedoch nicht immer eindeutig festlegen läßt. Sie können als Verbindungen einer der FormelnThe sulfonyltriazole derivatives according to the invention are each defined substances, but their structure cannot always be clearly established. You can use one of the formulas as connections
oderor
oder auch als Isomeren-Gemische vorliegen.or also as mixtures of isomers.
Die für die Formel (I) gewählte Schreibweise soll andeuten, dass sich die Positionen der Doppelbindungen im Triazol-Ring und die Bindungsstelle der -SO2-R2-Gruppe nicht in allen Fällen eindeutig ermitteln läßt.The notation chosen for formula (I) is intended to indicate that the positions of the double bonds in the triazole ring and the binding site of the -SO 2 -R 2 group cannot be clearly determined in all cases.
Die erfindungsgemäßen Stoffe sind durch die Formel (I) allgemein definiert.The substances according to the invention are generally defined by the formula (I).
Hai steht auch vorzugsweise für Fluor, Chlor oder Brom.Shark also preferably represents fluorine, chlorine or bromine.
R1 steht vorzugsweise für Wasserstoff, Alkyl mit 1 bis 6 Kohlenstoffatomen,R 1 preferably represents hydrogen, alkyl having 1 to 6 carbon atoms,
Alkoxyalkyl mit 1 bis 6 Kohlenstoffatomεn im Alkoyteil und 1 bis 6 Kohlenstoffatomen im Alkylteil, Cycloalkyl mit 3 bis 8 Kohlenstoffatomen oder für Alkylaminocarbonyl mit 1 bis 6 Kohlenstoffatomen im Alkylteil, oder R1 steht für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Halogen, Nitro, CrC6- Alkyl, Cj-Cg-Alkoxy, Cr Cg-Alkylthio, Ci-Cg-Halogenalkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, C]-Cg-Halogenalkoxy mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cj-Cg-Halogenalkylthio mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cyano und/oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,Alkoxyalkyl with 1 to 6 carbon atoms in the alkoy part and 1 to 6 carbon atoms in the alkyl part, cycloalkyl with 3 to 8 carbon atoms or for alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, or R 1 stands for phenyl, which can be monosubstituted to trisubstituted, identical or different, by halogen, nitro, C r C 6 -alkyl, C j -Cg-alkoxy, C r Cg-alkylthio, Ci-Cg-haloalkyl with 1 to 5 identical or different halogen atoms, C ] -Cg-haloalkoxy with 1 to 5 identical or different halogen atoms, Cj-Cg-haloalkylthio with 1 to 5 identical or different halogen atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms,
oderor
R1 steht für Phenoxy, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Halogen, Nitro, Cj-Cg-Alkyl, Cj-C^-Alkoxy, C C6-Alkylthio, C Cg-Halogenalkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cj-C6-Halogenalkoxy mit 1 bis 5 gleichen oder verschie- denen Halogenatomen, Cι-C6-Halogenalkylthio mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cyano und/oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,R 1 stands for phenoxy, which can be substituted once to three times, in the same way or differently, by halogen, nitro, C j -Cg-alkyl, C j -C ^ alkoxy, CC 6 -alkylthio, C Cg-haloalkyl with 1 to 5 same or different halogen atoms, C j -C 6 haloalkoxy with 1 to 5 identical or different halogen atoms, Cι-C 6 haloalkylthio with 1 to 5 identical or different halogen atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms,
oderor
R1 steht für einen Heterocyclyl-Rest mit 5 oder 6 Ringgliedern und 1 bis 3 Heteroatomen, wie Stickstoff, Sauerstoff und/oder Schwefel, wobei dieser Rest einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Halogen, Cyano, Nitro, Amino, Hydroxy, Alkyl mit 1 bis 4 Kohlen- Stoffatomen, Alkoxy mit 1 bis 4 Kohlenstoffatomen, Halogenalkyl mit 1 bis 4R 1 represents a heterocyclyl radical with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, where this radical can be monosubstituted to trisubstituted, identically or differently, by halogen, cyano, nitro, amino, Hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4
Kohlenstoffatomen und 1 bis 5 gleichen oder verschiedenen Halogenatomen, Halogenalkoxy mit 1 bis 4 Kohlenstoffatomen und 1 bis 5 gleichen oder verschiedenen Halogenatomen, Alkylcarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil, Alkoxycarbonyl mit 1 bis 3 Kohlenstoffatomen im Alkoxyteil, Carbamoyl, Alkyaminocarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil,Carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, alkoxycarbonyl with 1 to 3 carbon atoms in the alkoxy part, carbamoyl, alkyaminocarbonyl with 1 to 4 Carbon atoms in the alkyl part,
Dialkylaminocarbonyl mit 1 bis 4 Kohlenstoffatomen in den einzelnen Alkylteilen, Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 4 Kohlenstoffatomen in den einzelnen Alkylteilen oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen.Dialkylaminocarbonyl with 1 to 4 carbon atoms in each Alkyl parts, hydroximinoalkyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts or cycloalkyl having 3 to 6 carbon atoms.
R2 steht vorzugsweise für Alkyl mit 1 bis 6 Kohlenstoffatomen oder für einenR 2 preferably represents alkyl having 1 to 6 carbon atoms or one
Heterocyclyl-Rest mit 5 oder 6 Ringgliedern und 1 bis 3 Heteroatomen, wie Stickstoff, Sauerstoff und/oder Schwefel, wobei dieser Rest einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Halogen, Cyano, Nitro, Amino, Hydroxy, Alkyl mit 1 bis 4 Kohlenstoffatomen, Alkoxy mit 1 bis 4 Kohlenstoffatomen, Halogenalkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 5 gleichen oder verschiedenen Halogenatomen, Halogenalkoxy mit 1 bis 4 Kohlenstoffatomen und 1 bis 5 gleichen oder verschiedenen Halogenatomen, Alkylcarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil, Alkoxycarbonyl mit 1 bis 3 Kohlenstoffatomen im Alkoxyteil, Carbamoyl, Alkyaminocarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil, Dialkyl- aminocarbonyl mit 1 bis 4 Kohlenstoffatomen in den einzelnen Alkylteilen, Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 4 Kohlenstoffatomen in den einzelnen Alkylteilen oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen.Heterocyclyl radical with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, it being possible for this radical to be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, alkyl with 1 up to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, Alkoxycarbonyl with 1 to 3 carbon atoms in the alkoxy part, carbamoyl, alkyaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in the individual alkyl parts, hydroximinoalkyl or alkoximinoalkyl each with 1 to 4 carbon atoms in the individual alkyl parts or cycloalkyl with 3 up to 6 carbon atoms.
R2 steht außerdem vorzugsweise für einen Rest der FormelR 2 also preferably represents a radical of the formula
R3 steht vorzugsweise für Fluor, Chlor, Brom, Alkyl mit 1 bis 6 Kohlenstoffatomen oder für Phenyl.R 3 preferably represents fluorine, chlorine, bromine, alkyl having 1 to 6 carbon atoms or phenyl.
R4 steht vorzugsweise für Wasserstoff oder Alkyl mit 1 bis 6 Kohlenstoffatomen. R5 steht vorzugsweise für Alkyl mit 1 bis 6 Kohlenstoffatomen oder für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Halogen, Nitro, CrC6-Alkyl, C,-C6-Alkoxy, CrC6-Alkylthio, CrC6- Halogenalkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cj- C6-Halogenalkoxy mit 1 bis 5 gleichen oder verschiedenen Halogenatomen,R 4 preferably represents hydrogen or alkyl having 1 to 6 carbon atoms. R 5 preferably represents alkyl having 1 to 6 carbon atoms or phenyl which can be monosubstituted to trisubstituted, identical or different, by halogen, nitro, C r C 6 alkyl, C, -C 6 alkoxy, C r C 6 -Alkylthio, C r C 6 - haloalkyl with 1 to 5 identical or different halogen atoms, C j - C 6 -haloalkoxy with 1 to 5 identical or different halogen atoms,
C]-Cg-Halogen-alkylthio mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, Cyano und/oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen.C ] -Cg-Halogen-alkylthio with 1 to 5 identical or different halogen atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms.
R4 und R5 stehen außerdem auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, vorzugsweise für einen gesättigten heterocyclischen Ring mitR 4 and R 5 , together with the nitrogen atom to which they are attached, preferably also represent a saturated heterocyclic ring
5 oder 6 Ringgliedern, wobei der Ring ein weiteres Stickstoff- oder Sauerstoffatom enthalten kann und einfach bis vierfach, gleichartig oder verschieden substituiert sein kann durch Halogen und/oder Alkyl mit 1 bis 4 Kohlenstoffatomen.5 or 6 ring members, where the ring may contain a further nitrogen or oxygen atom and may be mono- to tetrasubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms.
Hai steht auch besonders bevorzugt für Fluor, Chlor oder Brom.Shark is also particularly preferably fluorine, chlorine or bromine.
R1 steht besonders bevorzugt für Wasserstoff. Methyl, Ethyl, n-Propyl, Iso- propyl, n-Butyl, sek.-Butyl, iso-Butyl oder tert.-Butyl, für Alkoxyalkyl mit 1 bis 4 Kohlenstoffatomen im Alkoxyteil und 1 bis 4 Kohlenstoffatomen imR 1 particularly preferably represents hydrogen. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, for alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the
Alkylteil, für Cycloalkyl mit 3 bis 7 Kohlenstoffatomen oder fürAlkyl part, for cycloalkyl having 3 to 7 carbon atoms or for
Alkylaminocarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil,Alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part,
oderor
Rl steht besonders bevorzugt für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy,R l particularly preferably represents phenyl which can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,
Trifluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl, oderTrifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl, or
R1 steht besonders bevorzugt für Phenoxy, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy, Tri- fluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl,R 1 particularly preferably represents phenoxy, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl
R1 steht außerdem besonders bevorzugt für Furyl. Thienyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1 ,2,4-Triazinyl, 1,3,5- Triazinyl, Pyrrolidinyl, Piperidinyl oder Morpholinyl, wobei diese hetero- cyclischen Reste einfach, zweifach oder dreifach, gleichartig oder verschieden substituiert sein können durch Fluor, Chlor. Brom, Cyano, Nitro, Amino, Hydroxy, Carbamoyl, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s-, oder t-Butyl, Cyclopropyl, Methoxy, Ethoxy, n- oder i-Propoxy, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy. Acetyl, Propionyl, Methoxy- carbonyl, Ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, Methox- iminomethyl, Ethoximinomethyl, Methoximinoethyl und Ethoximinoethyl.R 1 also particularly preferably represents furyl. Thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, Piperidinyl or morpholinyl, where these heterocyclic radicals can be substituted once, twice or three times, in the same way or differently, by fluorine, chlorine. Bromine, cyano, nitro, amino, hydroxy, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy. Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl.
R2 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl oder Isopropyl oder Furyl, Thienyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyridazinyl, Pyrazinyl,R 2 particularly preferably represents methyl, ethyl, n-propyl or isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrazinyl,
1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Pyrrolidinyl, Piperidinyl oder Morpholinyl, wobei diese heterocyclischen Reste einfach, zweifach oder dreifach, gleichartig oder verschieden substituiert sein können durch Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Carbamoyl, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s-, oder t-Butyl, Cyclopropyl, Methoxy, Ethoxy, n- oder i-Propoxy, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, Hydroximinomethyl, Hydroxyiminoethyl, Methoximinomethyl, Ethoximinomethyl, Methoximino- ethyl und Ethoximinoethyl.1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, piperidinyl or morpholinyl, it being possible for these heterocyclic radicals to be substituted once, twice or three times, in the same way or differently, by fluorine, chlorine , Bromine, cyano, nitro, amino, hydroxy, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy , Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroxyiminoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl.
R2 steht außerdem besonders bevorzugt für einen Rest der FormelR 2 also particularly preferably represents a radical of the formula
R3 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl, tert.-Butyl oder Phenyl.R 3 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or phenyl.
R4 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl oder tert.-Butyl.R 4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
R5 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl oder tert.-Butyl, oder für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propyl- thio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy,R 5 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, or phenyl which can be monosubstituted to trisubstituted in the same or different manner by Fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,
Difluorchlormethoxy, Trifluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl.Difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl.
R4 und R5 stehen äußerem auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt für Pyrrolidinyl, Piperidinyl,R 4 and R 5 also together with the nitrogen atom to which they are attached are particularly preferably pyrrolidinyl, piperidinyl,
Morpholinyl oder Piperazinyl, wobei jeder dieser Reste einfach bis vierfach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Methyl, Ethyl, n-Propyl, Isopropyl, nButyl, i-Butyl, sek.-Butyl oder tert.- Butyl. Hal steht ganz besonders bevorzugt für Chlor oder Brom.Morpholinyl or piperazinyl, where each of these residues can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl or tert-butyl . Hal very particularly preferably represents chlorine or bromine.
R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl oder tert.-Butyl, für Alkoyalkyl mit 1 oder 2 Kohlenstoffatomen im Alkoxyteil und 1 oder 2 Kohlenstoffatomen im Alkylteil, für Cyclopropyl, Cyclopentyl, Cyclohexyl oder für Alkylaminocarbonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil,R 1 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, for alkoyalkyl having 1 or 2 carbon atoms in the alkoxy part and 1 or 2 Carbon atoms in the alkyl part, for cyclopropyl, cyclopentyl, cyclohexyl or for alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part,
oderor
R1 steht ganz besonders bevorzugt für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluor- chlormethoxy, Trifluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl,R 1 very particularly preferably represents phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl and / or cyclohexyl
oderor
R1 steht ganz besonders bevorzugt für Phenoxy, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluor- chlormethoxy, Trifluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl,R 1 very particularly preferably represents phenoxy, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and / or cyclohexyl and / or cyclohexyl
R1 steht außerdem ganz besonders bevorzugt für Furyl, Thienyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl,R 1 also very particularly preferably represents furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl,
Thiadiazolyl, Pyridinyl, 1,2,4-Triazinyl, Pyrrolidinyl, Piperidinyl oder Morpholinyl, wobei diese heterocyclischen Reste einfach, zweifach oder dreifach, gleichartig oder verschieden substituiert sein können durch Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Carbamoyl, Methyl, Ethyl, n- oder i-Propyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethyl, Difluor- methoxy, Trifluormethoxy, Acetyl, Methoxycarbonyl, Ethoxycarbonyl,Thiadiazolyl, pyridinyl, 1,2,4-triazinyl, pyrrolidinyl, piperidinyl or Morpholinyl, where these heterocyclic radicals can be substituted once, twice or three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, carbamoyl, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, Ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl, ethoxycarbonyl,
Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximino- methyl, Methoximinoethyl und Ethoximinoethyl.Hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximino-methyl, methoximinoethyl and ethoximinoethyl.
R2 steht ganz besonders bevorzugt für Methyl, Ethyl, n-Propyl oder Isopropyl oder für Furyl, Thienyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl,R 2 very particularly preferably represents methyl, ethyl, n-propyl or isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl,
Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, 1 ,2,4-Triazinyl, Pyrrolidinyl, Piperidinyl oder Morpholinyl, wobei diese heterocyclischen Reste einfach, zweifach oder dreifach, gleichartig oder verschieden substituiert sein können durch Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Carbamoyl, Methyl, Ethyl, n- oder i-Propyl, Cyclopropyl, Methoxy,Thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, 1, 2,4-triazinyl, pyrrolidinyl, piperidinyl or morpholinyl, where these heterocyclic radicals can be substituted once, twice or three times, identically or differently by fluorine, chlorine, bromine, cyano, nitro , Amino, hydroxy, carbamoyl, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy,
Ethoxy, Trifluormethyl, Difluormethoxy. Trifluormethoxy, Acetyl, Methoxycarbonyl, Ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl und Ethoximinoethyl.Ethoxy, trifluoromethyl, difluoromethoxy. Trifluoromethoxy, acetyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl.
R2 steht außerdem ganz besonders bevorzugt für einen Rest der FormelR 2 also very particularly preferably represents a radical of the formula
R3 steht ganz besonders bevorzugt für Fluor. Chlor, Brom, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, tert.-Butyl oder Phenyl.R 3 very particularly preferably represents fluorine. Chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or phenyl.
R4 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, Isopropyl oder n-Butyl. R5 steht ganz besonders bevorzugt für Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl oder tert.-Butyl, oder für Phenyl, das einfach bis dreifach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, Methylthio, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, Cyano, Cyclopropyl, Cyclopentyl und/oder Cyclohexyl.R 4 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl or n-butyl. R 5 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, or phenyl, which can be monosubstituted to trisubstituted in the same or different manner by fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy , Cyano, cyclopropyl, cyclopentyl and / or cyclohexyl.
R4 und R5 stehen außerdem auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, ganz besonders bevorzugt für Pyrrolidinyl, Piperidinyl, Morpholinyl oder Piperazinyl, wobei jeder dieser Reste einfachbis vierfach, gleichartig oder verschieden substituiert sein kann durch Fluor, Chlor, Methyl und/oder Ethyl.R 4 and R 5 also together with the nitrogen atom to which they are attached very particularly preferably represent pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, where each of these radicals can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, methyl and / or ethyl.
Die zuvor angegebenen Substituenten-Bedeutungen können untereinander in beliebiger Weise kombiniert werden. Außerdem können auch einzelne Definitionen entfallen.The substituent meanings given above can be combined with one another in any manner. In addition, individual definitions can also be omitted.
Verwendet man 3-Phenyl-5-chlor-l,2,4-triazol und 3,5-Dimethyl-isoxazol-4- sulfonylchlorid als Ausgangsstoffe, so kann der Verlauf des erfindungsgemäßen Verfahrens durch das folgende Formelschema veranschaulicht werden:If 3-phenyl-5-chloro-l, 2,4-triazole and 3,5-dimethyl-isoxazole-4-sulfonyl chloride are used as starting materials, the course of the process according to the invention can be illustrated by the following formula:
Die bei der Durchführung des erfindungsgemäßen Verfahrens als Ausgangsstoffe benötigten Triazole sind durch die Formel (II) allgemein definiert. In dieser Formel haben R1 und Hai vorzugsweise diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) für diese Reste als bevorzugt genannt wurden. Formula (II) provides a general definition of the triazoles required as starting materials when carrying out the process according to the invention. In this formula, R 1 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
Die Triazole der Formel (II) können in den drei folgenden tautomeren Formen vorliegen.The triazoles of formula (II) can exist in the following three tautomeric forms.
oderor
Bei der erfindungsgemäßen Umsetzung mit Sulfonsäurehalogeniden der Formel (III) können sich also Endprodukte der Formel (I) bilden, die sich von den tautomeren Formen der Formeln (Ha), (Hb) und/oder (Hc) ableiten. Reagieren mehrereIn the reaction according to the invention with sulfonic acid halides of the formula (III), end products of the formula (I) can thus form which are derived from the tautomeric forms of the formulas (Ha), (Hb) and / or (Hc). Respond several
Tautomere, so erhält man Endprodukte der Formel (I) in Form von Gemischen. Die Triazole der Formel (II) sind bekannt oder lassen sich nach bekannten Methoden herstellen (vgl. J. prakt. Chem. 3 T2 (1970), 610-621).Tautomers, end products of the formula (I) are obtained in the form of mixtures. The triazoles of the formula (II) are known or can be prepared by known methods (cf. J. Prakt. Chem. 3 T2 (1970), 610-621).
Die zur Durchführung des erfindungsgemäßen Verfahrens als Reaktionskomponenten benötigten Sulfonsäurehalogenide sind durch die Formel (III) allgemein definiert. In dieser Formel hat R^ vorzugsweise diejenige Bedeutung, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt für R^ angegeben wurde. Hai1 steht vorzugsweise für Chlor.Formula (III) provides a general definition of the sulfonic acid halides required as reaction components for carrying out the process according to the invention. In this formula, R ^ preferably has the meaning which has already been given as preferred for R ^ in connection with the description of the compounds of the formula (I) according to the invention. Shark 1 is preferably chlorine.
Die Sulfonsäurehalogenide der Formel (III) sind bekannt oder können nach bekannten Verfahren hergestellt werden (vgl. J. Heterocyclic Chem. 1981, 997-1006 und EP-A 0 238 824).The sulfonic acid halides of the formula (III) are known or can be prepared by known processes (cf. J. Heterocyclic Chem. 1981, 997-1006 and EP-A 0 238 824).
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens kommen alle inerten organischen Lösungsmittel in Betracht. Vorzugsweise verwendbar sind aliphatische, alicyclische oder aromatische Kohlenwasserstoffe, wie Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; halogenierte Kohlenwasserstoffe, wie Chlorbenzol. Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Trichlorethan; Ether, wie Diethyl- ether, Diisopropylether, Methyl-t-butylether, Methyl-t-Amylether, Dioxan, Tetrahy- drofuran, 1 ,2-Dimethoxyethan, 1 ,2-Diethoxyethan oder Anisol; Ketone, wie Aceton, Butanon, Methyl-isobutylketon oder Cyclohexanon; Nitrile, wie Acetonitril, Propio- nitril, n- oder i-Butyronitril oder Benzonitril; Ester wie Essigsäuremethylester oder Essigsäureethylester.Suitable diluents for carrying out the process according to the invention are all inert organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as chlorobenzene. Dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1, 2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Esters such as methyl acetate or ethyl acetate.
Als Säurebindemittel kommen bei der Durchführung des erfindungsgemäßen Verfahrens alle üblichen anorganischen oder organischen Basen infrage. Vorzugsweise verwendbar sind Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alko- holate, -acetate, -carbonate oder -hydrogencarbonate. wie Natriumhydrid, Natrium- amid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Natriumacetat, Kaliumacetat, Calciumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbonat oder Natriumhydrogencarbonat, ferner Ammonium-Verbindungen, wie Ammoniumhydroxid, Ammoniumacetat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Suitable acid binders for carrying out the process according to the invention are all customary inorganic or organic bases. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates are preferably usable. such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, Potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl -benzylamine, pyridine, N-
Methylpiperidin, N-Methylmorpholin, N,N-Dimethylaminopyridin, Diazabi- cyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).Methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 150°C, vorzugsweise zwischen 10°C und 120°C.The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
Das erfindungsgemäße Verfahren wird im allgemeinen unter Atmosphärendruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem DruckThe process according to the invention is generally carried out under atmospheric pressure. It is also possible, however, under increased or reduced pressure
- im allgemeinen zwischen 0,1 bar und 10 bar - zu arbeiten.- generally between 0.1 bar and 10 bar - to work.
Zur Durchführung des erfindungsgemäßen Verfahrens setzt man pro Mol an Triazol der Formel (II) im allgemeinen 1 bis 2 Mol, vorzugsweise 1 bis 1 ,3 Mol, an Sulfon- säurehalogenid der Formel (III) und gegebenenfalls 1,0 bis 2,0 Mol, vorzugsweiseTo carry out the process according to the invention, 1 to 2 mol, preferably 1 to 1.3 mol, of sulfonic acid halide of the formula (III) and, if appropriate, 1.0 to 2.0 mol are generally employed per mol of triazole of the formula (II) , preferably
1,0 bis 1,3 Mol an Säureakzeptor ein.1.0 to 1.3 moles of acid acceptor.
Die Aufarbeitung erfolgt nach üblichen Methoden. Im allgemeinen verfährt man in der Weise, dass man das Reaktionsgemisch in Wasser gießt, das entstehende Gemisch mehrfach mit einem in Wasser wenig löslichen organischen Solvens extrahiert, die vereinigten organischen Phasen trocknet und unter vermindertem Druck einengt. Der verbleibende Rückstand kann gegebenenfalls nach üblichen Reinigungsmethoden von eventuell noch vorhandenen Verunreinigungen befreit werden. Die erfindungsgemäßen Stoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen, wie Fungi und Bakterien, im Pflanzenschutz und im Materialschutz eingesetzt werden.The processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is poured into water, the resulting mixture is extracted several times with an organic solvent which is sparingly soluble in water, and the combined organic phases are dried and concentrated under reduced pressure. The remaining residue can, if necessary, be freed from any impurities that may still be present using customary cleaning methods. The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
Fungizide lassen sich Pflanzenschutz zur Bekämpfung von Plasmodiophoromycetes,Fungicides can be used to control Plasmodiophoromycetes,
Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes und Deuteromycetes einsetzen.Use Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bakterizide lassen sich im Pflanzenschutz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen.Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen und bakteriellen Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt:Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas-Arten, wie beispielsweise Xanthomonas campestris pv. oryzae;Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas- Arten, wie beispielsweise Pseudomonas syringae pv. lachrymans;Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia- Arten, wie beispielsweise Erwinia amylovora;Erwinia species, such as, for example, Erwinia amylovora;
Pythium-Arten, wie beispielsweise Pythium ultimum; Phytophthora-Arten, wie beispielsweise Phytophthora infestans;Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora-Arten, wie beispielsweise Pseudoperonospora humuli oderPseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;Pseudoperonospora cubensis;
Plasmopara- Arten, wie beispielsweise Plasmopara viticola;Plasmopara species, such as, for example, Plasmopara viticola;
Bremia-Arten, wie beispielsweise Bremia lactucae; Peronospora- Arten, wie beispielsweise Peronospora pisi oder P. brassicae;Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe- Arten, wie beispielsweise Erysiphe graminis;Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea;Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha;Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia-Arten, wie beispielsweise Venturia inaequalis; Pyrenophora-Arten, wie beispielsweise Pyrenophora teres oder P. gramineaVenturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(Konidienform: Drechslera, Syn: Helminthosporium): Cochliobolus-Arten, wie beispielsweise Cochliobolus sativus(Conidial form: Drechslera, Syn: Helminthosporium): Cochliobolus species, such as, for example, Cochliobolus sativus
(Konidienform: Drechslera, Syn: Helminthosporium);(Conidial form: Drechslera, Syn: Helminthosporium);
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus;Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia- Arten, wie beispielsweise Puccinia recondita; Sclerotinia-Arten, wie beispielsweise Sclerotinia sclerotiorum;Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia- Arten, wie beispielsweise Tilletia caries;Tilletia species, such as, for example, Tilletia caries;
Ustilago-Arten, wie beispielsweise Ustilago nuda oder Ustilago avenae;Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia-Arten, wie beispielsweise Pellicularia sasakii;Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia-Arten, wie beispielsweise Pyricularia oryzae; Fusarium- Arten, wie beispielsweise Fusarium culmorum;Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum;
Botrytis-Arten, wie beispielsweise Botrytis cinerea;Botrytis species, such as, for example, Botrytis cinerea;
Septoria- Arten, wie beispielsweise Septoria nodorum;Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria- Arten, wie beispielsweise Leptosphaeria nodorum;Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora-Arten, wie beispielsweise Cercospora canescens; Alternaria- Arten, wie beispielsweise Alternaria brassicae;Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella-Arten, wie beispielsweise Pseudocercosporella herpotrichoides.Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdi- sehen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
Dabei lassen sich die erfindungsgemäßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Krankheiten im Wein-, Obst- und Gemüseanbau, wie beispielsweise gegen Phytophthora-Arten, einsetzen.The active compounds according to the invention can be used particularly successfully to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Phytophthora species.
Die erfindungsgemäßen Wirkstoffe eignen sich auch zur Steigerung des Ernteertrages. Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf. Im Material schütz lassen sich die erfindungsgemäßen Stoffe zum Schutz von technischen Materialien gegen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen.The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance. In the protective material, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebendeIn the present context, technical materials include non-living ones
Materialien zu verstehen, die für die Verwendung in der Technik zubereitet worden sind. Beispielsweise können technische Materialien, die durch erfindungsgemäße Wirkstoffe vor mikrobieller Veränderung oder Zerstörung geschützt werden sollen, Klebstoffe, Leime, Papier und Karton, Textilien, Leder, Holz, Anstrichmittel und Kunststoffartikel, Kühlschmierstoffe und andere Materialien sein, die von Mikroorganismen befallen oder zersetzt werden können. Im Rahmen der zu schützenden Materialien seien auch Teile von Produktionsanlagen, beispielsweise Kühlwasserkreisläufe, genannt, die durch Vermehrung von Mikroorganismen beeinträchtigt werden können. Im Rahmen der vorliegenden Erfindung seien als technische Materialien vorzugsweise Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Anstrichmittel,Understand materials that have been prepared for use in the art. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms . In the context of the materials to be protected, parts of production plants, for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms. In the context of the present invention, the preferred technical materials are adhesives, glues, papers and cartons, leather, wood, paints,
Kühlschmiermittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.Cooling lubricants and heat transfer liquids called, particularly preferably wood.
Als Mikroorganismen, die einen Abbau oder eine Veränderung der technischen Materialien bewirken können, seien beispielsweise Bakterien, Pilze, Hefen, Algen und Schleimorganismen genannt. Vorzugsweise wirken die erfindungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holzverfärbende und holzzerstörende Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
Es seien beispielsweise Mikroorganismen der folgenden Gattungen genannt:For example, microorganisms of the following genera may be mentioned:
Alternaria, wie Alternaria tenuis,Alternaria, such as Alternaria tenuis,
Aspergillus, wie Aspergillus niger,Aspergillus, such as Aspergillus niger,
Chaetomium, wie Chaetomium globosum,Chaetomium, like Chaetomium globosum,
Coniophora, wie Coniophora puetana, Lentinus, wie Lentinus tigrinus,Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,
Penicillium, wie Penicillium glaucum, Polyporus, wie Polyporus versicolor, Aureobasidium, wie Aureobasidium pullulans, Sclerophoma, wie Sclerophoma pityophila, Trichoderma, wie Trichoderma viride, Escherichia, wie Escherichia coli,Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,
Pseudomonas, wie Pseudomonas aeruginosa, Staphylococcus, wie Staphylococcus aureus.Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/oder chemischen Eigenschaften in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-Kalt- und Warmnebel-Formulierungen.Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aro- maten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorefhylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdöl- fraktionen, Alkohole, wie Butanol oder Glycol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Als feste Trägerstoffe kommen in Frage: z.B. natürliche Ge- steinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmo- rillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengel. Als Emulgier und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emul- gatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweiß- hydrolysate. Als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorefhylenes 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 sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Possible solid carriers are: for example natural stone powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates. Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholi- pide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 GewichtsprozentThe formulations generally contain between 0.1 and 95 percent by weight
Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.Active ingredient, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Fungiziden, Bakteriziden, Akariziden, Nematiziden oder Insektiziden verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern oder Resistenzentwicklungen vorzubeugen. In vielen Fällen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung ist größer als die Wirksamkeit der Einzelkomponenten.The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases you get it synergistic effects, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
Als Mischpartner kommen zum Beispiel folgende Verbindungen in Frage:The following connections can be considered as mixed partners:
Fungizide:Fungicides:
Aldimorph, Ampropylfos, Ampropylfos-Kalium, Andoprim, Anilazin, Azaconazol, Azoxystrobin,Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-isobutyl, Bialaphos,Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,
Binapacryl, Bion, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazol, Bupirimat, Buthiobat,Binapacryl, bion, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calciumpolysulfid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinomethionat), Chlobenthiazon, Chlorfenazol, Chloroneb,Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb,
Chloropicrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cypro- conazol, Cyprodinil, Cyprofuram,Chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,
Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Dietho- fencarb, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazol, Diniconazol-M,Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M,
Dinocap, Diphenylamin, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,
Ediphenphos, Epoxiconazol, Etaconazol, Ethirimol, Etridiazol,Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet. Fosetyl-Alminium, Fosetyl- Natrium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarbonil, Furconazol,Famoxadone, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimidol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolut. Fosetyl-aluminum, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
Furconazol-cis, Furmecyclox, Guazatin,Furconazole-cis, furmecyclox, Guazatin,
Hexachlorobenzol, Hexaconazol, Hymexazol,Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobenfos (IBP), Iprodione, Irumamycin, Isoprothiolan, Iso- valedione,Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovededione,
Kasugamycin, Kresoxim-methyl, Kupfer-Zubereitungen, wie: Kupferhydroxid,Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide,
Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mischung,Copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
Mildiomycin, Myclobutanil, Myclozolin,Mildiomycin, myclobutanil, myclozolin,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol,Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Natrium, Propiconazol, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Pyroxyfur,Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazol, Quintozen (PCNB), Quinoxyfen,Quinconazole, quintozen (PCNB), quinoxyfen,
Schwefel und Schwefel-Zubereitungen, Tebuconazol, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazol, Thiabendazol, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Triticonazol,Sulfur and sulfur preparations, Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazol,Uniconazole,
Validamycin A, Vinclozolin, Viniconazol, Zarilamid, Zineb, Ziram sowie Dagger G,Validamycin A, vinclozolin, viniconazole, zarilamide, zineb, ziram and Dagger G,
OK-8705, OK-8801, α-( 1 , 1 -Dimethylethyl)-ß-(2-phenoxyethyl)- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(2,4-Dichlorphenyl)-ß-fluor-b-propyl- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(2,4-Dichlorphenyl)-ß-methoxy-a-methyl- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(5-Methyl-l,3-dioxan-5-yl)-ß-[[4-(trifluormethyl)-phenyl]-methylen]-lH-l,2,4- triazol-1 -ethanol,OK-8705, OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -ß-fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -ß-methoxy-a-methyl-1 H-1, 2,4 -triazol-1-ethanol, α- (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-triazole -1-ethanol,
(5RS,6RS)-6-Hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanon, (E)-a-(Methoxyimino)-N-methyl-2-phenoxy-phenylacetamid, {2-Methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbaminsäure-(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-l, 2,4-triazol-l-yl) -3-octanone, (E) -a- (methoxyimino ) -N-methyl-2-phenoxy-phenylacetamide, {2-methyl-l - [[[[l- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid-
1 -isopropylester1-isopropyl ester
1 -(2,4-Dichlorphenyl)-2-( 1 H- 1 ,2,4-triazol-l -yl)-ethanon-0-(phenylmethyl)-oxim, 1 -(2-Methyl- 1 -naphthalenyl)- 1 H-pyrrol-2,5-dion, l-(3,5-Dichlorphenyl)-3-(2-propenyl)-2,5-pyrrolidindion, 1 -[(Diiodmethyl)-sulfonyl]-4-methyl-benzol, l-[[2-(2,4-Dichlorphenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazol, l-[[2-(4-Chlo henyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazol, l-[l-[2-[(2,4-Dichlorphenyl)-methoxy]-phenyl]-ethenyl]-lH-imidazol, l-Methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, 2',6'-Dibrom-2-methyl-4'-trifluormethoxy-4'-trifluor-methyl-l,3-thiazol-5- carboxanilid, 2,2-Dichlor-N-[l-(4-chlorphenyl)-ethyl]-l-ethyl-3-methyl-cyclopropancarboxamid,1 - (2,4-dichlorophenyl) -2- (1 H- 1, 2,4-triazol-l -yl) -ethanone-0- (phenylmethyl) -oxime, 1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione, l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1 - [(diiodomethyl) sulfonyl] -4-methyl- benzene, l - [[2- (2,4-dichlorophenyl) -1, 3-dioxolan-2-yl] methyl] -IH-imidazole, l - [[2- (4-chloro-henyl) -3-phenyloxiranyl ] -methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -lH-imidazole, l-methyl-5 -nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-Dichlor-5-(methylthio)-4-pyrimidinyl-thiocyanat,2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-Dichlor-N-(4-trifluormethylbenzyl)-benzamid,2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-Dichlor-N-[[4-(trifluormethyl)-phenyl]-methyl]-benzamid, 2-(2,3,3-Triiod-2-propenyl)-2H-tetrazol,2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2-[(l-Methylethyl)-sulfonyl]-5-(trichlormethyl)-l,3,4-thiadiazol,2 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -1, 3,4-thiadiazole,
2-[[6-Deoxy-4-O-(4-O-methyl-ß-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4- methoxy- 1 H-pyrrolo[2,3-d]pyrimidin-5-carbonitril,2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4-methoxy-1 H-pyrrolo [2,3-d] pyrimidine -5-carbonitrile,
2-Aminobutan, 2-Brom-2-(brommethyl)-pentandinitril,2-aminobutane, 2-bromo-2- (bromomethyl) pentandinitrile,
2-Chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridincarboxamid,2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide,
2-Chlor-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamid,2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-Phenylphenol(OPP),2-phenylphenol (OPP),
3,4-Dichlor-l -[4-(difluormethoxy)-phenyl]- 1 H-pyrrol-2,5-dion, 3,5-Dichlor-N-[cyan[(l-methyl-2-propynyl)-oxy]-methyl]-benzamid,3,4-dichloro-l - [4- (difluoromethoxy) phenyl] - 1 H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyan [(l-methyl-2-propynyl) - oxy] methyl] benzamide,
3-(l , 1 -Dimethylpropyl- 1 -oxo-1 H-inden-2-carbonitril,3- (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile,
3-[2-(4-Chloφhenyl)-5-ethoxy-3-isoxazolidinyl]-pyridin,3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-Chlor-2-cyan-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazol-l-sulfonamid,4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -lH-imidazole-l-sulfonamide,
4-Methyl-tetrazolo[l,5-a]quinazolin-5(4H)-on, 8-(l,l-Dimethylethyl)-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decan-2-methanamin,4-methyl-tetrazolo [l, 5-a] quinazolin-5 (4H) -one, 8- (l, l-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decan-2 -methanamine,
8 -Hydroxy chinolinsulfat,8 -hydroxy quinoline sulfate,
9H-Xanthen-9-carbonsäure-2-[(phenylamino)-carbonyl]-hydrazid, bis-(l-Methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophendicarboxylat, eis- 1 -(4-Chlorphenyl)-2-( 1 H- 1 ,2,4-triazol- 1 -yl)-cycloheptanol, cis-4-[3-[4-(l,l-Dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholin- hydrochlorid,9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chlorophenyl) -2- (1 H-1, 2,4-triazole-1-yl) cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) phenyl -2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride,
Ethyl-[(4-chlθφhenyl)-azo]-cyanoacetat,Ethyl - [(4-chlθφhenyl) azo] cyanoacetate,
Kaliumhydrogencarbonat,Potassium hydrogen carbonate,
Methantetrathiol-Natriumsalz, Methyl- 1 -(2,3 -dihydro-2,2-dimethy 1- 1 H-inden- 1 -yl)- 1 H-imidazol-5 -carboxy lat,Methane tetrathiol sodium salt, methyl 1 - (2,3-dihydro-2,2-dimethyl 1- 1 H-inden-1-yl) - 1 H-imidazole-5-carboxy lat,
Methyl-N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninat, Methyl-N-(chloracetyl)-N-(2,6-dimethylphenyl)-DL-alaninat,Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N-(2,3-Dichlor-4-hydroxyphenyl)-l-methyl-cyclohexancarboxamid.N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexane carboxamide.
N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamid,N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamid, N-(2-Chlor-4-nitrophenyl)-4-methyl-3-nitro-benzolsulfonamid,N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro- benzenesulfonamide,
N-(4-Cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidinamin,N- (4-cyclohexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine,
N-(4-Hexylphenyl)- 1 ,4,5 ,6-tetrahydro-2-pyrimidinamin,N- (4-hexylphenyl) - 1, 4,5, 6-tetrahydro-2-pyrimidinamine,
N-(5-Chlor-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamid,N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,
N-(6-Methoxy)-3-pyridinyl)-cyclopropancarboxamid, N-[2,2,2-Trichlor-l-[(chloracetyl)-amino]-ethyl]-benzamid,N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide, N- [2,2,2-trichloro-l - [(chloroacetyl) amino] ethyl] benzamide,
N- [3 -Chlor-4,5-bis-(2-propinyloxy)-phenyl] -N ' -methoxy -methanimidamid,N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N '-methoxy-methanimidamide,
N-Formyl-N-hydroxy-DL-alanin -Natriumsalz,N-formyl-N-hydroxy-DL-alanine sodium salt,
O,O-Diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioat,O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-Methyl-S-phenyl-phenylpropylphosphoramidothioat, S-Methyl- 1 ,2,3-benzothiadiazol-7-carbothioat, spiro[2H]- 1 -Benzopyran-2, 1' (3 'H)-isobenzofuran]-3 '-on,O-methyl-S-phenyl-phenylpropylphosphoramidothioat, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] - 1-benzopyran-2, 1 '(3' H) -isobenzofuran] -3 ' -on,
Bakterizide:Bactericides:
Bromopol, Dichlorophen, Nitrapyrin, Nickel-dimethyldithiocarbamat, Kasugamycin,Bromopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb. Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin.Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb. Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin.
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviren, Beauveria bassiana, Beauveria tenella. Bendiocarb, Benfuracarb,Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella. Bendiocarb, Benfuracarb,
Bensultap, Benzoximate, Betacyfluthrin. Bifenazate. Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Buto- carboxim, Butylpyridaben,Bensultap, Benzoximate, Betacyfluthrin. Bifenazate. Bifenthrin, bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos. Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaphorthrin, Cis-Resmethrin, Cispermethrin,Cadusafos, carbaryl, carbofuran, carbophenothione, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos. Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaphorthrin, Cis-Resmethrin, Cispermethrin,
Clocythrin, Cloethocarb, Clofentezine, Cyanophos. Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,Clocythrin, cloethocarb, clofentezine, cyanophos. Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylanphosynofen, Diolol Dodinophosphin, Diolentin, Diolentin, Difolubin, Diolentin, Difolubin, Diolentin, Difolubin, Diolentin, Difolubin, Diolentin
Elfusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin. Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate,Elfusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxide, Fenitrothion, Fenothiocarb, Fenoxpyrin, pyroxin, pyroxin Fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,
Flufenoxuron, Flutenzine, Fluvalinate, Fonophos. Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb, Granuloseviren, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivermecfin,Flufenoxuron, Flutenzine, Fluvalinate, Fonophos. Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb, Granuloseviren, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivermecfin,
Kernpolyederviren, Lambda-cyhalothrin, Lufenuron,Nuclear polyhedron viruses, lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Metaldehyd, Methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, Methidathion, Methiocarb. Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin. Monocrotophos,Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae, metharhilic flavoviride, methidathione, methiocarb. Methomyl, methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin. Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M,Naled, Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M,
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenophos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion,Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenophos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion,
Pyrimidifen, Pyriproxifen,Pyrimidifen, pyriproxifen,
Quinalphos,Quinalphos,
Ribavirin, Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,Ribavirin, Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau-fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron,Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,
Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Thetacyper- methrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon,Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Thetacyper- methrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocethriniazine, Tralocethriniazin
Triflumuron, Trimethacarb,Triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecaniiVamidothion, Vaniliprole, Verticillium lecanii
YI 5302YI 5302
Zeta-Cypermethrin, Zolaprofos (lR-cis)-[5-(Phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)- furanyliden)-methyl]-2,2-dimethylcyclopropancarboxylat,Zeta-cypermethrin, zolaprofos (IR-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2- dimethylcyclopropane carboxylate,
(3-Phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylat, l-[(2-Chlor-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazin-2(lH)- imin, 2-(2-Chlor-6-fluoφhenyl)-4-[4-(l,l-diemthylethyl)phenyl]-4,5-dihydro-oxazol,(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate, l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5- triazin-2 (lH) - imine, 2- (2-chloro-6-fluoφhenyl) -4- [4- (l, l-dimethylethyl) phenyl] -4,5-dihydro-oxazole,
2-(Acetyloxy)-3 -docecyl- 1 ,4-naphthalinidion,2- (acetyloxy) -3-docecyl- 1, 4-naphthalinidione,
2-Chlor-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamid,2-chloro-N - [[[4- (l-phenylethoxy) phenyl] amino] carbonyl] benzamide,
2-Chlor-N-[[[4-(2,2-dichlor- 1 , 1 -difluorethoxy)-phenyl]-amino]-carbonyl]-benzamid,2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide,
3 -Methylphenyl-propy lcarbamat, 4-[4-(4-Ethoxyphenyl)-4-methylpentyl]-l-fluor-2-phenoxy-benzol,3-methylphenyl propyl carbamate, 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene,
4-Chlor-2-(l,l-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-4-chloro-2- (l, l-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -
3 (2H)-pyridazinon,3 (2H) pyridazinone,
4-Chlor-2-(2-chlor-2-methy lpropy l)-5 - [(6-iod-3 -pyridiny l)methoxy ] -3 (2H)- pyridazinon, 4-Chlor-5[(6-chlor-3-pyridinyl)-methoxy]-2-(3,4-dichlθφhenyl)-3(2H)-pyridazinon,4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone, 4-chloro-5 [(6- chloro-3-pyridinyl) methoxy] -2- (3,4-dichloro-phenyl) -3 (2H) -pyridazinone,
Bacillus thuringiensis strain EG-2348, Benzoesäure (2-benzoyl- 1 -( 1 , 1 -dimethylethyl)-hydrazid,Bacillus thuringiensis strain EG-2348, Benzoic acid (2-benzoyl-1 - (1,1-dimethylethyl) hydrazide,
Butan 2,2-dimethyl-3-(2,4-dichlθφhenyl)-2-oxo-l-oxaspiro[4.5]dec-3-en-4-yl-ester, [3-[(6-Chlor-3-pyridinyl)methyl]-2-thiazolidinyliden]-cyanamid, Dihydro-2-(nitromethylen)-2H- 1 ,3-thiazine-3(4H)-carboxaldehyd, Ethyl-[2-[[l,6-dihydro-6-oxo-l-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamat,Butane 2,2-dimethyl-3- (2,4-dichloro-phenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester, [3 - [(6-chloro-3- pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide, dihydro-2- (nitromethylene) -2H- 1,3-thiazine-3 (4H) -carboxaldehyde, ethyl- [2 - [[1,6-dihydro-6- oxo-l- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate,
N-(3 ,4,4-Trifluor- 1 -oxo-3 -buteny l)-glycin,N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine,
N-(4-Chlθφhenyl)-3-[4-Difluormethoxy)phenyl]-4,5-dihydro-4-phenyl-lH-pyrazol- 1 -carboxamid,N- (4-chloro-phenyl) -3- [4-difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,
N-[(2-Chlor-5-thiazolyl)-methyl]-N'-methyl-N"-nitro-guanidin, N-Methyl-N'-(l-methyl-2-propenyl)-l,2-hydrazindicarbothioamid,N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine, N-methyl-N '- (l-methyl-2-propenyl) -l, 2-hydrazinedicarbothioamide ,
N-Methyl-N'-2-propenyl-l,2-hydrazindicarbothioamid, O,O-Diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioat.N-methyl-N'-2-propenyl-l, 2-hydrazinedicarbothioamide, O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren ist möglich.A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden.The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung von Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 10 g pro Kilogramm Saatgut. Bei der Behandlung des Bodens liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 1 und 5.000 g/ha.When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
Die zum Schutz technischer Materialien verwendeten Mittel enthalten die Wirkstoffe im allgemeinen in einer Menge von 1 bis 95 Gewichts-%, bevorzugt von 10 bis 75 Gewichts-%.The agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95% by weight, preferably 10 to 75% by weight.
Die Anwendungskonzentrationen der erfindungsgemäßen Wirkstoffe richten sich nach der Art und dem Vorkommen der zu bekämpfenden Mikroorganismen sowie nach der Zusammensetzung des zu schützenden Materials. Die optimale Einsatzmenge kann durch Testreihen ermittelt werden. Im allgemeinen liegen die Anwendungskonzentrationen im Bereich von 0,001 bis 5 Gewichts-%, vorzugsweise von 0,05 bis 1,0 Gewichts-% bezogen auf das zu schützende Material.The application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
Die Wirksamkeit und das Wirkungsspektrum der erfindungsgemäß im Materialschutz zu verwendenden Wirkstoffe bzw. der daraus herstellbaren Mittel, Konzentrate oder ganz allgemein Formulierungen kann erhöht werden, wenn gegebenenfalls weitere antimikrobiell wirksame Verbindungen, Fungizide, Bakterizide, Herbizide, Insektizide oder andere Wirkstoffe zur Vergrößerung des Wirkungsspektrums oder Erzielung besonderer Effekte wie z.B. dem zusätzlichen Schutz vor Insekten zugesetzt werden. Diese Mischungen können ein breiteres Wirkungsspektrum besitzen als die erfindungsgemäßen Verbindungen.The effectiveness and the spectrum of activity of the active ingredients to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients are used to enlarge the spectrum of activity or Achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
Die Herstellung und die Verwendung von erfindungsgemäßen Wirkstoffen werden durch die folgenden Beispiele veranschaulicht.The preparation and use of active compounds according to the invention are illustrated by the following examples.
Die erfindungsgemäßen Sulfonyl-triazol-Derivate der Formel (I) können auch zur Behandlung transgener Pflanzen eingesetzt werden. Dabei können im Zusammenwirken mit den durch Expression gebildeten Substanzen auch synergistische Effekte auftreten. HerstellungsbeispieleThe sulfonyl-triazole derivatives of the formula (I) according to the invention can also be used for the treatment of transgenic plants. In cooperation with the substances formed by expression, synergistic effects can also occur. Manufacturing examples
Beispiel 1example 1
Eine Lösung von 1,8 g (10 mmol) 3-Phenyl-5-chlor-l,2,4-triazol in 40 ml Acetonitril wird bei Raumtemperatur unter Rühren mit 1,4 g (10 mmol) Kaliumcarbonat versetzt und danach 10 Minuten bei Raumtemperatur gerührt. Anschließend fügt man 2,0 g (10 mmol) 3,5-Dimethyl-isoxazol-4-sulfonylchlorid hinzu und rührt weitere 20 Stun- den bei Raumtemperatur. Zur Aufarbeitung wird das Reaktionsgemisch in 150 mlA solution of 1.8 g (10 mmol) of 3-phenyl-5-chloro-l, 2,4-triazole in 40 ml of acetonitrile is mixed with 1.4 g (10 mmol) of potassium carbonate at room temperature with stirring and then for 10 minutes stirred at room temperature. Then 2.0 g (10 mmol) of 3,5-dimethyl-isoxazole-4-sulfonyl chloride are added and the mixture is stirred for a further 20 hours at room temperature. For working up, the reaction mixture is in 150 ml
Wasser gegossen. Das dabei entstandene Gemisch wird zweimal mit je 40 ml Methylenchlorid extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet und unter vermindertem Druck eingeengt. Der verbleibende Rückstand wird mit Methylenchlorid als Laufmittel an Kieselgel chromatographiert. Man erhält auf diese Weise 1,7 g (50 % der Theorie) an 3-Phenyl-5-chlor-2-(3,4-dimethyl- isoxazol-4-sulfonyl)-l,2,4-triazol in Form einer Festsubstanz vom Schmelzpunkt 70 bis 74°C. log p: 3,67Poured water. The resulting mixture is extracted twice with 40 ml of methylene chloride. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The remaining residue is chromatographed on silica gel using mobile phase methylene chloride. In this way, 1.7 g (50% of theory) of 3-phenyl-5-chloro-2- (3,4-dimethyl-isoxazole-4-sulfonyl) -1, 2,4-triazole are obtained in the form of a Solid substance with a melting point of 70 to 74 ° C. log p: 3.67
Nach der oben angegebenen Methode werden auch die in der folgenden Tabelle aufgeführten Sulfonyltriazol-Derivate der Formel (I) hergestellt. Tabelle 1The sulfonyltriazole derivatives of the formula (I) listed in the following table are also prepared by the method given above. Table 1
*) Die Bestimmung der logP- Werte erfolgte gemäß EEC-Directive 79/831 Annex V. A 8 durch HPLC (Gradientenmethode; Acetoniril/0,1 % wässrige Phosphorsäure). *) The logP values were determined in accordance with EEC Directive 79/831 Annex V. A 8 by HPLC (gradient method; acetoniril / 0.1% aqueous phosphoric acid).
VerwendungsbeispieleExamples of use
Beispiel AExample A
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Lösungsmittel: 47 Gewichtsteile AcetonSolvent: 47 parts by weight of acetone
Emulgator: 3 Gewichtsteile Alkyl-Aryl-PolyglykoletherEmulsifier: 3 parts by weight of alkyl aryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzu- bereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wässrigen Sporensuspension von Phytoph- thora infestans inokuliert. Die Pflanzen werden dann in einer Inkubationskabine bei ca. 20°C und 100 % relativer Luftfeuchtigkeit aufgestellt.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at approx. 20 ° C and 100% relative humidity.
3 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird.Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Wirkstoffe, Aufwandmengen und Versuchsergebnisse gehen aus der folgenden Tabelle hervor. Tabelle AActive substances, application rates and test results are shown in the following table. Table A
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective

Claims

Patentansprücheclaims
1. Sulfonyltriazol-Derivate der Formel1. Sulfonyltriazole derivatives of the formula
in welcherin which
Hai für Fluor, Chlor oder Brom steht,Shark represents fluorine, chlorine or bromine,
R' für Wasserstoff, Alkyl, Alkoxyalkyl, Cycloalkyl, Alkylamino- carbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy oder für gegebenenfalls substituiertes Heterocyclyl steht undR 'represents hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenyl, optionally substituted phenoxy or for optionally substituted heterocyclyl and
R2 für Alkyl oder für gegebenenfalls substituiertes Heterocyclyl steht oder für einen Rest der FormelR 2 represents alkyl or optionally substituted heterocyclyl or a radical of the formula
steht, worinstands in what
R3 für Halogen, Alkyl oder Phenyl steht,R 3 represents halogen, alkyl or phenyl,
R4 für Wasserstoff oder Alkyl steht und R5 für Alkyl oder gegebenenfalls substituiertes Phenyl steht,R 4 represents hydrogen or alkyl and R 5 represents alkyl or optionally substituted phenyl,
oderor
R4 und R5 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring bilden, der substituiert sein kann und auch ein zusätzliches Heteroatom enthalten kann.R 4 and R 5 together with the nitrogen atom to which they are attached form a heterocyclic ring which can be substituted and can also contain an additional hetero atom.
Verfahren zur Herstellung von Sulfonyltriazol-Derivaten der Formel (I) gemäß Anspruch 1 , dadurch gekennzeiclmet, dass man Triazole der FormelProcess for the preparation of sulfonyltriazole derivatives of the formula (I) according to Claim 1, characterized in that triazoles of the formula
in welcherin which
R1 und Hai die oben angegebenen Bedeutungen haben,R 1 and shark have the meanings given above,
mit Sulfonsäurehalogeniden der Formelwith sulfonic acid halides of the formula
R2-S02-Hal' (III) in welcherR 2 -S0 2 -Hal '(III) in which
R2 die oben angegebene Bedeutung hat undR 2 has the meaning given above and
Hai' für Chlor oder Brom steht, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.Shark 'represents chlorine or bromine, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
3. Mittel zur Bekämpfung von unerwünschten Mikroorganismen, gekennzeich- net durch einen Gehalt an mindestens einem Sulfonyltriazol-Derivat der3. Agents for combating undesired microorganisms, characterized by a content of at least one sulfonyltriazole derivative of
Formel (I) gemäß Anspruch 1 neben Streckmitteln und/oder oberflächenaktiven Stoffen.Formula (I) according to claim 1 in addition to extenders and / or surface-active substances.
4. Verwendung von Sulfonyltriazol-Derivaten der Formel (I) gemäß Anspruch 1 zur Bekämpfung von unerwünschten Mikroorganismen.4. Use of sulfonyltriazole derivatives of the formula (I) according to Claim 1 for combating undesired microorganisms.
5. Verfahren zur Bekämpfung von unerwünschten Mikroorganismen, dadurch gekennzeichnet, dass man Sulfonyltriazol-Derivate der Formel (I) auf die Mikroorganismen und/oder deren Lebensraum ausbringt.5. A method of combating undesirable microorganisms, characterized in that sulfonyltriazole derivatives of the formula (I) are applied to the microorganisms and / or their habitat.
6. Verfahren zur Herstellung von Mitteln zur Bekämpfung von unerwünschten Mikroorganismen, dadurch gekennzeichnet, dass man Sulfonyltriazol- Derivate der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.6. A process for the preparation of agents for controlling undesirable microorganisms, characterized in that sulfonyltriazole derivatives of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances.
7. Sulfonyltriazol-Derivat gemäß Anspruch 1 , gekennzeichnet durch die Formel7. sulfonyltriazole derivative according to claim 1, characterized by the formula
Sulfonyltriazol-Derivat gemäß Anspruch 1, gekennzeichnet durch die Formel Sulfonyltriazole derivative according to claim 1, characterized by the formula
9. Sulfonyltriazol-Derivat gemäß Anspruch 1, gekennzeichnet durch die Formel9. sulfonyltriazole derivative according to claim 1, characterized by the formula
EP99946189A 1998-09-29 1999-09-20 Sulfonyltriazol derivatives and their use for combating micro-organisms Withdrawn EP1117654A1 (en)

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