EP0796253A1 - 1,3,4-oxathiazol-2-ones fongicides - Google Patents

1,3,4-oxathiazol-2-ones fongicides

Info

Publication number
EP0796253A1
EP0796253A1 EP95941027A EP95941027A EP0796253A1 EP 0796253 A1 EP0796253 A1 EP 0796253A1 EP 95941027 A EP95941027 A EP 95941027A EP 95941027 A EP95941027 A EP 95941027A EP 0796253 A1 EP0796253 A1 EP 0796253A1
Authority
EP
European Patent Office
Prior art keywords
cyano
optionally
carbon atoms
substituted
methyl
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Withdrawn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
EP95941027A
Other languages
German (de)
English (en)
Inventor
Ulrich Heinemann
Ralf Tiemann
Stefan Dutzmann
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 EP0796253A1 publication Critical patent/EP0796253A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
    • C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
    • C07D291/04—Five-membered rings
    • 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
    • A01N43/82—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 three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new oxathiazolinones, a process for their preparation and their use as fungicides.
  • E stands for a 1-alkene-1, 1-diyl grouping which contains a radical R 1 in the 2-position, or for a 2-aza-1-alkene-1, 1-diyl grouping which is in 2 - Position contains a radical R 2 , or for an optionally substituted imino group ("Azamethylene" NR 3 ) or for a 3-aza-1 - propene-2,3-diyl group, which is in the 1 position Radical R 4 and in the 3-position contains a radical R 5 or stands for a 3-aza-1-propene-2,3-diyl grouping which contains a radical R 4 in the 1-position, or for a 3-thia -1-propen-2,3-diyl grouping which contains a R 4 radical in the 1 position or a 1-aza-1-propene-2,3-diyl grouping which has a radical in the 1 position R 6 and in the 3-position contains a radical R 5 , or for one
  • 1-aza-1-propene-2,3-diyl grouping which contains a radical R 4 in the 1-position and a radical R 5 in the 3-position or for a 1 3-diaza-1-propene-2,3 - Diyl grouping is in the 1 position a radical R 6 and in the 3 position one Radical R 5 contains, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R 6 in the 1-position, or represents a 1-aza-3-thia -1- propen-2,3-diyl grouping which contains a radical R 6 in the 1-position, wherein
  • R 1 , R 4 represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
  • R 2 , R 6 represents hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and R 3 represents hydrogen. Cyano or for each optionally substituted
  • Alkyl Alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
  • R 5 represents alkyl, a single bond, oxygen, sulfur or alkane diyl, alkenediyl, alkynediyl or one of the following, each optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl
  • -CH 2 -ON C (R 7 ) -, -N (R 8 ) -CQ-Q-, -CQ-N (R 8 ) -CQ-Q-,
  • R 7 for hydrogen. Cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
  • R 8 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl, Z for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl,
  • Aryl or heterocyclyl is Aryl or heterocyclyl.
  • Ar, E, G and Z have the meaning given above, with chlorocarbonylsulfonic acid chloride, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
  • the compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E- and Z-. Both the E and the Z isomers as well as any mixtures of these isomers are claimed.
  • the invention preferably relates to compounds of the formula (I) in which
  • Ar represents in each case optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which represents oxygen, sulfur or nitrogen and optionally one or two more represent nitrogen, the possible substituents preferably being selected from the list below are
  • R 1 is hydrogen, halogen, cyano or for alkyl, alkoxy, alkylthio which is optionally substituted by halogen, cyano or C 1 -C 4 -alkoxy.
  • R 3 represents hydrogen, cyano or each optionally halogenated.
  • R 6 represents hydrogen, amino, cyano or alkyl, alkoxy, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C 1 -C 4 alkoxy, each having 1 to 6 carbon atoms in the alkyl radicals and represents a single bond, oxygen, Sulfur or for alkanediyl, alkenediyl, alkynediyl each having up to 4 carbon atoms or one of the following groups, optionally substituted by halogen, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl
  • Q oxygen or sulfur
  • R 7 for hydrogen, cyano, for optionally by halogen.
  • Alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for each optionally by halogen, cyano.
  • R 8 is hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C 1 -C 4 alkoxy or is substituted by halogen, cyano, carboxy, C 1 -C 4 - Alkyl or C1-C4-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms represents, optionally optionally single or multiple, identical or different by halogen, cyano, hydroxy, amino, C 1 -C 4 alkoxy, C 1 -C 4 - Alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl (which are each optionally replaced by
  • Halogen can be substituted) substituted alkyl having 1 to 8 carbon atoms
  • alkenyl or alkynyl each optionally substituted by halogen, each having up to 8 carbon atoms,
  • phenyl, naphthyl or heterocyclyl with 3 to 7 ring members each of which is optionally mono- or polysubstituted by identical or different substituents, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents being preferred halogen, cyano, nitro, amino, hydroxy, formyl, carboxy are selected from the following list.
  • Carbamoyl
  • Thiocarbamoyl each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfominyl or halogen each with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched halogenoalkene i or haloalkenyloxy each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkyl
  • Heterocyclyl or heterocyclyl-methyl each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - and in each case optionally in the phenyl, pyridyl or thienyl part once or more, same or different through
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine. Chlorine or bromine, especially for fluorine or chlorine.
  • the invention relates in particular to compounds of the formula (I) in which
  • Ar for optionally substituted ortho-, meta- or para-phenylene, for furandiyl.
  • Fluorine Chlorine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy.
  • Methylthio Methylsulfinyl or methylsulfonyl
  • R 1 for hydrogen, fluorine, chlorine, bromine, cyano or for methyl, ethyl, propyl, methoxy, ethoxy which is in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethow.
  • Methylamino, ethylamino or dimethylamino R 2 represents hydrogen, amino, cyano or in each case optionally by fluorine. Chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino.
  • R 3 for hydrogen, cyano or for methyl, ethyl n- or i-propyl, n-, i- or s-butyl, optionally substituted by fluorine, cyano, methoxy or ethoxy, for allyl or propargyl or for in each case optionally by fluorine, Chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl substituted
  • R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
  • R 5 represents methyl, ethyl n- or i-propyl, n-, i- or s-butyl and
  • R 6 represents hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, represents a single bond, oxygen, sulfur or each optionally by fluorine, chlorine, bromine, hydroxy, methyl. Ethyl.
  • n- or i-Propyl trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted methylene, dimethylene (ethane-1,2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the following groups
  • Q represents oxygen or sulfur
  • R 7 represents hydrogen, cyano, optionally by fluorine. Chlorine, cyano,
  • R 8 represents hydrogen, hydroxyl, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy or optionally by Fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally optionally up to five times by fluorine, chlorine, bromine, cyano, hydroxy, Amino, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each
  • allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methylpropargyl which are each mono- to trisubstituted by fluorine, chlorine or bromine;
  • phenyl which is optionally monosubstituted to trisubstituted.
  • Pyridazinyl Pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxiranyl, oxetanyl, tetrahydro colryl.
  • Perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl where the possible substituents are preferably selected from the list below: Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,
  • a particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
  • Q oxygen or sulfur
  • R 7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl
  • R 8 represents hydrogen, methyl, ethyl or cyclopropyl
  • Difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl Methoxy carbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl. Methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy.
  • Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • Z 1 represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below;
  • Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • Z 2 represents in each case monosubstituted to trisubstituted, identically or differently, phenyl, pyridyl or pyrimidyl, the possible substituents preferably being selected from the list below
  • n- or i-propyl n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally singly or multiply, the same or different substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case two-linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio. Benzyl. Benzyloxy or benzylthio.
  • Formula (II) provides a general definition of the carboxamides required as starting materials for carrying out the process according to the invention.
  • Ar, E, G and Z preferably or in particular have those meanings which have been preferred or particularly preferred for Ar, E, G and in connection with the description of the compounds of the formula (I) according to the invention Z were specified.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf., for example, EP-A 468 775). Chlorocarbonyl sulfonic acid chloride is a well-known reagent in organic chemistry.
  • the process according to the invention is preferably carried out without, but optionally also in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides.
  • alcoholates such as, for example
  • Potassium hydrogen carbonate sodium hydrogen carbonate or ammonium carbonate. and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline,
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBN diazabicycloundecene
  • the process according to the invention is optionally carried out in the presence of a diluent all conventional organic solvents are suitable.
  • organic solvents include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide
  • reaction temperatures can be varied within a wide range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 180 ° C, preferably at temperatures between 20 ° C and 130 ° C.
  • the method according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • To carry out the process according to the invention generally 1 to 10 mol, preferably 1.0 to 3 mol, particularly preferably 1.5 to 2.5 mol of chlorocarbonylsulfonyl chloride are used per mol of carboxamide of the formula (II).
  • the reaction products are carried out, worked up and isolated using known processes (cf. the preparation examples).
  • the active compounds according to the invention have a strong microbicidal action and are used practically to combat unwanted microorganisms.
  • the active compounds are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Some pathogens of fungal diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation;
  • 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 Pseudoperonospora cubense
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubense
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or Peronospora brassicae;
  • Erysiphe species such as, for example, Erysrphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Sleepiginea
  • 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 Pyrenophora graminea (conidial form Drechslera. Synonym Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form Drechslera. Svnonvm Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • 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, Pelhcularia sasakii;
  • Pvricularia species such as, for example, Pyricularia oryzae;
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrvtis 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 are particularly successful in combating cereal diseases, for example against Erysiphe species, Leptosphaeria, Pvrenophora and Cochliobolus species or for diseases in wine, fruit and vegetable cultivation, for example against Podospherea and Plasmopara Species used
  • the active ingredients may be converted into customary formulations, such as, for example, solutions. Emulsions. Suspensions, powders, foams, pastes. Granules, aerosols, very fine encapsulations in polymeric substances and in shell compounds for seeds, as well as 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, 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, it is also possible, for example, to use organic solvents as auxiliary agents.
  • Aromatic compounds such as xylene are essentially suitable as liquid solvents. Toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes. Chlorethylene. or methylene chloride.
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, are strongly polar Solvents, such as dimethylformamide or 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;
  • Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: e.g., kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse
  • emulsifying and / or foam-generating agents are possible: for example non-ionogenic 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 hydrolyzates;
  • emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • dispersants for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers are optionally used in the formulations, such as, for. B. Gum arabic. Polyvinyl alcohol. Polyvinyl acetate. as well as natural phospholipids. such as cephalins and lecithins and synthetic phospholipids. Other possible additives are 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.
  • 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 are also mixed with known fungicides, bactericides, acaricides, nematicides or insecticides, for example to broaden the spectrum of activity or to prevent the development of resistance.
  • Dichlorophene Diclobutrazole. Diclofluanide, diclomezin. Dicloran. Diethofencarb,
  • Difenoconazole Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenylamine, Dipyrithion, Ditalimfos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazol,
  • Imazalil Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan, Kasugamycin, copper preparations such as copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
  • Azinphos M Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos,
  • Chlorfluazuron Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
  • Fipronil Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb.
  • Methamidophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
  • Tebufenozid Tebufenpyrad
  • Tebupirimphos Teflubenzuron
  • Tefluthrin Temephos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenethriazonium, Triomenethriazonium, Tri
  • the active compounds according to the invention are also mixed with other known active compounds, such as herbicides or with fertilizers and growth regulators.
  • the active ingredients are 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, dusting agents and granules.
  • the application is carried out in the customary manner, for example by pouring, spraying, spraying, scattering, Dusting, foaming, brushing, etc.
  • the active ingredients are applied using the ultra-low-volume process or the active ingredient preparation or the active ingredient itself is injected into the soil. If appropriate, the seeds of the plants are also treated.
  • the active compound concentrations in the use forms can be varied within a substantial range and are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001
  • active compound In the case of seed treatment, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required. When treating the soil, active substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action
  • Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative air humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation.
  • the following compound of preparation example (1) shows an efficacy of 100% with an active compound application rate of 250 g / ha
  • Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether 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 with water to the desired concentration
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules
  • Evaluation is carried out 7 days after the inoculation.
  • the following compound from preparation example (1) shows an efficacy of 100% with an active compound application rate of 250 g / ha.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether 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 with water to the desired concentration
  • young plants are sprayed with the active compound preparation. After the spray coating has dried on, the plants are washed with an aqueous spore suspension of inoculated and then remain in a moist chamber at 20 to 22 ° C and 100% relative humidity for 1 day. The plants are then placed in a greenhouse at 21 ° C. and about 90% humidity for 5 days. The plants are then moistened and placed in a moist chamber for 1 day. Evaluation is carried out 6 days after the inoculation
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 10 days after the inoculation.
  • the following compound from preparation example (1) shows an efficiency of 85% at an active ingredient concentration of 100 ppm

Abstract

L'invention concerne de nouvelles oxathiazolinones de formule (I), un procédé permettant de les produire ainsi que leur utilisation sous forme de fongicides.
EP95941027A 1994-12-08 1995-11-27 1,3,4-oxathiazol-2-ones fongicides Withdrawn EP0796253A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4443640 1994-12-08
DE19944443640 DE4443640A1 (de) 1994-12-08 1994-12-08 Oxathiazolinone
PCT/EP1995/004666 WO1996017835A1 (fr) 1994-12-08 1995-11-27 1,3,4-oxathiazol-2-ones fongicides

Publications (1)

Publication Number Publication Date
EP0796253A1 true EP0796253A1 (fr) 1997-09-24

Family

ID=6535218

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95941027A Withdrawn EP0796253A1 (fr) 1994-12-08 1995-11-27 1,3,4-oxathiazol-2-ones fongicides

Country Status (4)

Country Link
EP (1) EP0796253A1 (fr)
AU (1) AU4256896A (fr)
DE (1) DE4443640A1 (fr)
WO (1) WO1996017835A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6689372B1 (en) 1998-08-04 2004-02-10 Ciba Specialty Chemicals Corporation Microbicidal active substances

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1542685C3 (de) * 1965-05-07 1973-11-08 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen Herbizide
JP3188286B2 (ja) * 1991-08-20 2001-07-16 塩野義製薬株式会社 フェニルメトキシイミノ化合物およびそれを用いる農業用殺菌剤
GB9307247D0 (en) * 1993-04-07 1993-06-02 Zeneca Ltd Fungicidal compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9617835A1 *

Also Published As

Publication number Publication date
WO1996017835A1 (fr) 1996-06-13
AU4256896A (en) 1996-06-26
DE4443640A1 (de) 1996-06-13

Similar Documents

Publication Publication Date Title
EP0712396B1 (fr) Azadioxacycloalcenes substitues et leur utilisation comme fongicides
WO1996023763A1 (fr) Amides d'acide alcoximinoacetique
DE4443641A1 (de) Substituierte Carbonsäureamide
DE4408005A1 (de) Substituierte Azadioxacycloalkene
EP0842146B1 (fr) Derives d'acide acrylique et d'oxymether et leur utilisation comme fongicides
EP0805805B1 (fr) Arylazadioxacycloalcenes substitues fongicides
EP0779884B1 (fr) Derives d'imido-acides et leur utilisation comme pesticides
EP0749419A1 (fr) Derives d'oxime et leur utilisation comme pesticides
EP0809637B1 (fr) Aza-heterocycloalcenes et leur utilisation comme fongicides
EP0840721B1 (fr) Derives d'amide d'acide carboxylique et leur utilisation comme pesticides
EP0741695B1 (fr) Derives de l'acide hydroxamique, leur procede de fabrication et leur utilisation comme fongicides
EP0772587B1 (fr) Derives de n-alcoxy-amidine et leur utilisation comme pesticides
DE4426757A1 (de) 2-Imidazolidinon-Derivate
EP0796253A1 (fr) 1,3,4-oxathiazol-2-ones fongicides
WO1995021833A1 (fr) Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides
DE19512617A1 (de) Hydrazonoessigsäureamide
DE4419587A1 (de) Heterocyclische Imino-Derivate
DE19508573A1 (de) Imidsäurederivate
DE19510297A1 (de) Substituierte Heterocycloalkene
DE19602094A1 (de) Substituierte Carbamide
WO1996038411A1 (fr) Carbamides substitues et leur application comme agents phytosanitaires, en particulier comme fongicides
DE4422154A1 (de) Oxim-Derivate
DE19543199A1 (de) Alkoximinoessigsäureamide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19970708

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB

17Q First examination report despatched

Effective date: 19971120

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19990421