EP1114036A1 - Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables - Google Patents

Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables

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Publication number
EP1114036A1
EP1114036A1 EP99969088A EP99969088A EP1114036A1 EP 1114036 A1 EP1114036 A1 EP 1114036A1 EP 99969088 A EP99969088 A EP 99969088A EP 99969088 A EP99969088 A EP 99969088A EP 1114036 A1 EP1114036 A1 EP 1114036A1
Authority
EP
European Patent Office
Prior art keywords
formula
methyl
alkyl
oxazolones
sulfonyloxazolones
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Withdrawn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
EP99969088A
Other languages
German (de)
English (en)
Inventor
Lutz Assmann
Manfred Jautelat
Ulrike Wachendorff-Neumann
Klaus Stenzel
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 AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1114036A1 publication Critical patent/EP1114036A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D263/36—One oxygen atom
    • C07D263/38—One oxygen atom attached in position 2

Definitions

  • the present invention relates to new sulfonyloxazolones, a process for their preparation and their use for controlling unwanted microorganisms.
  • R 1 represents alkyl or optionally substituted heterocyclyl or a radical of the formula
  • R 3 represents halogen, alkyl or phenyl
  • R 4 represents hydrogen or alkyl
  • R 5 represents alkyl or optionally substituted phenyl
  • R 2 represents alkyl
  • R 2 has the meaning given above
  • R 1 has the meaning given above and Hal represents chlorine or bromine
  • the sulfonyloxazolones of the formula (I) have very good microbicidal properties and can be used to combat unwanted microorganisms in crop protection and in agriculture.
  • Formula (I) has a better activity against undesired microorganisms, in particular against fungi, than the structurally most similar, previously known substances with the same direction of action.
  • R 1 preferably represents alkyl having 1 to 4 carbon atoms or a heterocyclyl radical with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, which radical can contain a keto or imino group and can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, haloalkyl having 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,
  • R 1 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 r 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,
  • Ci-Cg-haloalkylthio with 1 to 5 identical or different halogen atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms.
  • R 2 preferably represents alkyl having 1 to 6 carbon atoms.
  • R 1 particularly preferably represents methyl, ethyl, propyl, isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrirnidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl , 1,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, piperidinyl or morpholinyl, it being possible for these radicals to be substituted once, twice or three times, in the same or different manner, by fluorine, chlorine, bromine, cyano, nitro, amino , Hydroxyl, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-
  • R 1 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 2 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
  • R 1 very particularly preferably represents methyl, ethyl, isopropyl or furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, 1, 2,4-triazinyl, pyrroli- dinyl, piperidinyl or morpholinyl, where these radicals can be substituted once, twice or three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, carbamoyl, methyl, ethyl, n- or i-propyl, cyclopropyl , Methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl, eth
  • R ' 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,
  • 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.
  • R 2 also very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
  • the substituent meanings given above can be combined with one another in any manner. In addition, individual definitions can also be omitted.
  • Formula (II) provides a general definition of the oxazolones required as starting materials when carrying out the process according to the invention.
  • R 2 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • the oxazolones of the formula (II) are hitherto unknown. They can be produced by using hydroxyketones of the formula in a first step
  • R 2 has the meaning given above
  • Formula (IV) provides a general definition of the hydroxy ketones required as starting materials for carrying out this process.
  • R ⁇ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • hydroxyketones of the formula (IV) are known or can be prepared by known methods.
  • reaction temperatures can be varied within a substantial range when carrying out the above process for the preparation of oxazolones of the formula (II).
  • the first step is carried out at temperatures between 10 ° C. and 160 ° C., preferably between 20 ° C. and 140 ° C.
  • the second step is generally carried out at temperatures between 10 ° C. and 100 ° C., preferably between 20 ° C. and 80 ° C.
  • both the first step and the second step are generally carried out under atmospheric pressure. But it is also possible to work under increased pressure.
  • the reaction mixture is concentrated, the remaining residue via an adsorbent Filtered material, the residue obtained after concentrating the eluate is stirred with water and the resulting precipitate is suction filtered and dried.
  • the intermediate is reacted with an excess of phosphorus oxychloride.
  • the processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is suctioned off through an adsorbent material, the filtrate is added to water, the resulting mixture is extracted with a water-insoluble organic solvent and the combined organic phases are dried and concentrated under reduced pressure.
  • 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 1 preferably has the meaning which has already been stated as preferred for R 1 in connection with the description of the compounds of the formula (I) according to the invention.
  • X preferably represents 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 isobuty
  • 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, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, are preferably usable.
  • Sodium hydroxide, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide are preferably usable.
  • 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 20 ° 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 Any remaining residue can, if necessary, be freed of 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 protect against undesired microorganisms, such as fungi and bacteria, in crop protection and in the material.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • 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
  • 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 with particularly good success 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 are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected from 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 attack or decompose from microorganisms can be.
  • adhesives glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which attack or decompose from microorganisms can be.
  • Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, 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 ones according to the invention preferably act
  • microorganisms of the following genera may be mentioned: Alternaria, such as Alternaria tenuis,
  • Aspergillus such as Aspergillus niger, Chaetomium, such as 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 compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes,
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers are those 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.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, natural rock 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: eg 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.
  • Possible emulsifiers and / or foaming 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 dispersing agents are, for example, lignin sulfite waste 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 of active compound, 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 synergistic effects are obtained, ie the effectiveness of the mixture is greater than that
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianon, dithianon, dithianon,
  • Fenpiclonil fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl-Sodium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarboniloxol, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil, Furcarbonil
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin
  • Tebuconazole Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutichlamidid, Triazoxid, Triazoxid
  • Tricyclazole tridemorph, triflumizole, triforin, triticonazole,
  • Methane tetrathiol sodium salt Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-y 1) - 1 H-imidazole-5-carboxy lat,
  • N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
  • Fenamiphos Fenazaquin, Fenbutatinoxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxanone Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses, Lambda-cyhalothrin, Lufenuron,
  • Mecarbam Metaldehyde, Methamidophos, Metharhilic anisopliae, Metharhilic flavoviride, Methidathion, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyramo, Oxidomylonomidamyl, Oxitomyl, Oxitomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat,
  • Pirimiphos M Profenophos, Promecarb, Propoxur, Prothiophos, Prothoat,
  • Triazamates triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron,
  • 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 watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using 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 from 1 to 95% by weight, preferably from 10 to
  • 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 substances to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to increase the activity. Spectrum or achieving special effects such as the additional protection from
  • Insects can be added. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • 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.
  • Emulsifier 3 parts by weight of alkyl aryl polyglycol ether

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  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (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 sulfonyloxazolones de la formule (I) dans laquelle R1 désigne alkyle ou hétérocyclyle éventuellement substitué ou un reste de la formule (a) ou (b) où R3 désigne halogène, alkyle ou phényle, R4 désigne hydrogène ou alkyle et R5 désigne alkyle ou phényle éventuellement substitué, et R2 désigne alkyle. L'invention concerne en outre un procédé de préparation desdites substances et leur utilisation pour lutter contre des micro-organismes indésirables. L'invention concerne par ailleurs de nouveaux produits intermédiaires de la formule (II) et un procédé permettant de les préparer.
EP99969088A 1998-09-16 1999-09-09 Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables Withdrawn EP1114036A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19842353A DE19842353A1 (de) 1998-09-16 1998-09-16 Sulfonyloxazolone
DE19842353 1998-09-16
PCT/EP1999/006650 WO2000015620A1 (fr) 1998-09-16 1999-09-09 Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables

Publications (1)

Publication Number Publication Date
EP1114036A1 true EP1114036A1 (fr) 2001-07-11

Family

ID=7881127

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99969088A Withdrawn EP1114036A1 (fr) 1998-09-16 1999-09-09 Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables

Country Status (10)

Country Link
US (2) US6359142B1 (fr)
EP (1) EP1114036A1 (fr)
JP (1) JP2002524555A (fr)
KR (1) KR20010079748A (fr)
CN (1) CN1318060A (fr)
AU (1) AU5975599A (fr)
BR (1) BR9913809A (fr)
DE (1) DE19842353A1 (fr)
PL (1) PL346522A1 (fr)
WO (1) WO2000015620A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102209496B1 (ko) 2019-03-21 2021-01-29 한진전자공업주식회사 라디에이터와 열교환용 마개의 오링 자동 조립장치 및 그 조립방법

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3931213A (en) * 1974-12-18 1976-01-06 Interx Research Corporation 3-Chloro-2-oxazolidinones
US4097262A (en) * 1977-04-22 1978-06-27 E. I. Du Pont De Nemours And Company Herbicidal acetamides
US4957933A (en) * 1989-04-21 1990-09-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5223523A (en) * 1989-04-21 1993-06-29 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
ZW8594A1 (en) * 1993-08-11 1994-10-12 Bayer Ag Substituted azadioxacycbalkenes
DE19609060A1 (de) * 1995-08-10 1997-02-13 Bayer Ag Halogenbenzimidazole
DE19623207A1 (de) * 1996-06-11 1997-12-18 Bayer Ag Imidazolderivate
DE19642865A1 (de) * 1996-10-17 1998-04-23 Bayer Ag Sulfonylbenzazolone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0015620A1 *

Also Published As

Publication number Publication date
KR20010079748A (ko) 2001-08-22
CN1318060A (zh) 2001-10-17
US20020107403A1 (en) 2002-08-08
PL346522A1 (en) 2002-02-11
AU5975599A (en) 2000-04-03
US6359142B1 (en) 2002-03-19
BR9913809A (pt) 2001-06-19
WO2000015620A1 (fr) 2000-03-23
DE19842353A1 (de) 2000-03-23
JP2002524555A (ja) 2002-08-06

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