EP1117654A1 - Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes - Google Patents

Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes

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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Withdrawn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)
English (en)
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/fr
Withdrawn legal-status Critical Current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.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne de nouveaux dérivés de sulfonyltriazol de la formule (I) où Hal représente du fluor, chlore ou brome, R<1> représente de l'hydrogène, alkyle, alcoxyalkyle, cycloalkyle, alkylaminocarbonyle, phényle éventuellement substitué, phénoxy éventuellement substitué ou hétérocyclyle éventuellement substitué et R<2 >représente alkyle ou hétérocyclyle éventuellement substitué ou un reste de la formule (a), où R<3> représente halogène, alkyle ou phényle, R<4> représente de l'hydrogène ou alkyle et R<5> représente alkyle ou phényle éventuellement substitué, ou bien R<4> et R<5> forment, avec l'atome d'azote auquel ils sont liés, un noyau hétérocyclique pouvant être substitué, voire pouvant contenir un hétéroatome supplémentaire. L'invention concerne un procédé de production de ces substances et leur utilisation pour lutter contre les micro-organismes indésirables.
EP99946189A 1998-09-29 1999-09-20 Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes Withdrawn EP1117654A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19844497A DE19844497A1 (de) 1998-09-29 1998-09-29 Sulfonyltriazol-Derivate
DE19844497 1998-09-29
PCT/EP1999/006938 WO2000018742A1 (fr) 1998-09-29 1999-09-20 Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes

Publications (1)

Publication Number Publication Date
EP1117654A1 true EP1117654A1 (fr) 2001-07-25

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EP99946189A Withdrawn EP1117654A1 (fr) 1998-09-29 1999-09-20 Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes

Country Status (10)

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US (2) US6384066B1 (fr)
EP (1) EP1117654A1 (fr)
JP (1) JP2002525360A (fr)
KR (1) KR20010079861A (fr)
CN (1) CN1320119A (fr)
AU (1) AU5863999A (fr)
BR (1) BR9914078A (fr)
DE (1) DE19844497A1 (fr)
PL (1) PL346903A1 (fr)
WO (1) WO2000018742A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10063178A1 (de) * 2000-12-18 2002-06-20 Bayer Ag Sulfonylpyrrole

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3605714A1 (de) 1986-02-22 1987-08-27 Bayer Ag Mikrobizide mittel
EP0284277A1 (fr) * 1987-03-21 1988-09-28 AgrEvo UK Limited Fongicides de cyanoimidazole
JPH02174758A (ja) * 1988-12-27 1990-07-06 Ishihara Sangyo Kaisha Ltd 含窒素五員環化合物、それらの製造方法及びそれらを含有する有害生物防除剤
DE19523446A1 (de) 1995-06-28 1997-01-02 Bayer Ag Benzotriazole
DE19623207A1 (de) 1996-06-11 1997-12-18 Bayer Ag Imidazolderivate
WO1999002518A1 (fr) 1997-07-11 1999-01-21 Nippon Soda Co., Ltd. Composes pyridyltriazole, procedes de production associes, et germicides agricoles et horticoles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0018742A1 *

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AU5863999A (en) 2000-04-17
PL346903A1 (en) 2002-03-11
BR9914078A (pt) 2001-06-19
DE19844497A1 (de) 2000-03-30
JP2002525360A (ja) 2002-08-13
KR20010079861A (ko) 2001-08-22
CN1320119A (zh) 2001-10-31
US6384066B1 (en) 2002-05-07
WO2000018742A1 (fr) 2000-04-06
US6566383B2 (en) 2003-05-20
US20030032811A1 (en) 2003-02-13

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