EP0743941A1 - Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides - Google Patents

Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides

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Publication number
EP0743941A1
EP0743941A1 EP95906997A EP95906997A EP0743941A1 EP 0743941 A1 EP0743941 A1 EP 0743941A1 EP 95906997 A EP95906997 A EP 95906997A EP 95906997 A EP95906997 A EP 95906997A EP 0743941 A1 EP0743941 A1 EP 0743941A1
Authority
EP
European Patent Office
Prior art keywords
cyano
substituted
methyl
alkyl
carbon atoms
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Withdrawn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
EP95906997A
Other languages
German (de)
English (en)
Inventor
Thomas Seitz
Lutz Assmann
Herbert Gayer
Peter Gerdes
Ulrich Heinemann
Bernd-Wieland Krüger
Dietmar Kuhnt
Ralf Tiemann
Heinz-Wilhelm Dehne
Stefan Dutzmann
Gerd Hänssler
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 EP0743941A1 publication Critical patent/EP0743941A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • 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
    • A01N43/74—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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/06—Seven-membered rings having the hetero atoms in positions 1 and 3

Definitions

  • the invention relates to new substituted oxazacycloalkenes, a process and new intermediates for their preparation and the use of oxazacycloalkenes and corresponding intermediates as fungicides.
  • A represents optionally substituted alkanediyl (alkylene)
  • Ar represents optionally substituted arylene or heteroarylene
  • E represents a 1-alkene-1,1-diyl grouping which contains a radical R 1 - in the 2-position, or a 2-aza-l-alkene-1,1-diyl grouping which is in 2- position contains a radical R 2 , or represents a 3-aza-l-propene-2,3-diyl grouping which contains a radical R in the 3 position and a radical R 1 in the 1 position, or for is an l-aza-l-propene-2,3-diyl grouping which contains a radical R 2 in the 1-position, or represents a 1,3-diaza-l-propene-2,3-diyl grouping , which contains a R radical in the 3-position and a R ⁇ radical in the 1-position, or represents an optionally substituted imino group ("Azamethylene", NR 3 ),
  • R represents alkyl
  • R, R, R independently of one another represent hydrogen, halogen, cyano or each optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
  • G for oxygen for alkanediyl, alkenediyl optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl.
  • n the numbers 0, 1 or 2
  • Q represents oxygen or sulfur
  • R 4 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
  • R 5 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl, and
  • Cycloalkyl aryl or heterocyclyl.
  • X represents halogen, hydroxy or a leaving group bonded via oxygen
  • the compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of E and Z isomers, but optionally also of optical isomers and diastereomers. It both the E and the Z isomers as well as any mixtures of the. further possible isomers claimed.
  • the invention preferably relates to compounds of the formula (I) in which
  • Ar stands for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being as follows The following are selected:
  • Y represents oxygen, sulfur, methylene (CH 2 ) or alkylimino (NR),
  • R represents alkyl having 1 to 6 carbon atoms
  • R 1 halogen, cyano or optionally substituted by halogen, cyano or C ⁇ j alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each Al ⁇ 1 in the alkyl radicals for hydrogen up to 6 carbon atoms,
  • R for hydrogen, amino, cyano or for each optionally by
  • R 3 represents hydrogen, cyano or alkyl, alkenyl or alkynyl, each optionally substituted by halogen, cyano or C j -C 4 alkoxy, each having up to 6 carbon atoms, or each optionally substituted by halogen, cyano, carboxy, C 1 -C 4 Alkyl or C r C 4 -alkoxy-carbonyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part, G for oxygen, each optionally by halogen, hydroxy, C, -C 4 -
  • n the numbers 0, 1 or 2
  • Q oxygen or sulfur
  • R 4 represents hydrogen, cyano, each alkyl, alkoxy, alkylthio optionally substituted by halogen, cyano or C 1 -C 4 alkoxy,
  • R 5 for hydrogen, hydroxy, cyano or for optionally by
  • alkyl optionally substituted by halogen, cyano, hydroxy, amino, CC 4 -alkoxy, C j - alkylthio, C 1 -C 4 alkylsulfonyl or C r C 4 alkylsulfonyl (which are each optionally substituted by halogen) with 1 to 8 carbon atoms, each for alkenyl or alkynyl optionally substituted by halogen, each with up to 8 carbon atoms, for each optionally by halogen, cyano, carboxy, phenyl (which optionally by halogen, cyano, C, -C 4 alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy or C ] -C 4 haloalkoxy is substituted), CC 4 -alkyl or C r C 4 -alkoxy-carbonyl-substituted cycloalkyl with 3 to 6 carbon atoms, for each optionally
  • Halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy.
  • 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, in particular fluorine or chlorine.
  • the invention relates in particular to compounds of the formula (I) in which
  • E represents one of the groupings below -Y. _ Y.
  • Y represents oxygen, sulfur, methylene (CH 2 ) or alkylimino (NR),
  • R represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,
  • R 1 for hydrogen, fluorine, chlorine, bromine, cyano or for methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy or dimethylamino,
  • R ⁇ for hydrogen, amino, cyano or for each optionally by
  • R 3 represents hydrogen, cyano or methyl, ethyl n- or i- which are each optionally substituted by fluorine, cyano, methoxy or ethoxy.
  • G for oxygen for in each case optionally substituted by fluorine, chlorine, hydroxyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, methylene, dimethylene (ethane-1,2- diyl), ethene-l, 2-diyl, ethyne-l, 2-diyl or one of the following Grup: pierieux
  • n the numbers 0, 1 or 2
  • Q oxygen or sulfur
  • R 4 is hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, meth-, ethoxy, propoxy, butoxy, which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, Methylthio, ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for each optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl sub ⁇ substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
  • R 5 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 ge optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, and
  • Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, for each optionally substituted phenyl , Naphthyl, furyl, tetrahydro colryl, benzofuryl, tetrahydropyranyl, thienyl, benzothienyl,
  • Oxygen (as a substitute for two geminal hydrogen atoms), 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,
  • Ethylsulfonyloxy hydroximinomethyl, hydroximinoethyl, methoximino-methyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally mono- or polysubstituted identically or differently by fluorine, chlorine, methyl, ethyl, n- or i-propyl, and in each case optionally in the phenyl moiety one or more times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy, eth
  • a particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
  • Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • R 1 and R 2 each represent methoxy
  • G represents oxygen, methylene or one of the groupings below
  • n represents the numbers 0, 1 or 2
  • R 4 represents hydrogen, methyl or ethyl
  • R 5 represents hydrogen, methyl or ethyl
  • radical definitions apply to the specified radical combinations in the specified preferred ranges and also between the specified ranges of preferred compounds. That is, the definition of a residue from any preferred area is combined with any other residue in all of its preferred areas.
  • Formula (II) provides a general definition of the substituted carboxylic acid amides to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I).
  • A, Ar, E, G and Z preferably or in particular those meanings that already.
  • X preferably represents fluorine, chlorine, bromine or iodine, hydroxy, CpC 4 alkylsulfonyloxy or phenylsulfonyloxy optionally substituted by chlorine or methyl, in particular chlorine, hydroxy, methylsulfonyloxy, phenylsulfonyloxy or tolylsulfonyloxy.
  • the substituted carboxamides of the formula (II) - like the substituted oxazacycloalkenes of the formula (I) - have strong fungicidal activity.
  • Y represents halogen, hydroxy or alkoxy
  • a and X have the meaning given above, optionally in the presence of a reaction auxiliary such as triethylamine.
  • a reaction auxiliary such as triethylamine.
  • Pyridine or 4-dimethylamino-pyridine and optionally in the presence of a diluent, such as methylene chloride or toluene, at temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C (cf. Position examples).
  • the compounds of formula (II) in which X represents halogen can also be obtained by reacting compounds of formula (II) in which X represents hydroxy with halogenating agents, e.g. Thionyl chloride or phosphorus (III) bromide, optionally in the presence of a diluent, e.g. Methylene chloride or chloroform, can be obtained at temperatures between 0 ° C and 100 ° C (see. The preparation examples).
  • halogenating agents e.g. Thionyl chloride or phosphorus (III) bromide
  • a diluent e.g. Methylene chloride or chloroform
  • the carboxylic acid derivatives to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (II) are generally defined by the formula (III).
  • Ar, E, G and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of formula (I) as preferred or as particularly preferred for Ar, E, G and Z have been specified;
  • Y preferably represents chlorine, hydroxy, methoxy or ethoxy.
  • the starting materials of the formula (III) are known and / or can be prepared by processes which are known per se (cf. EP-A 178826, EP-A 242081, EP-A 382375, EP-A 493711).
  • Formula (IV) provides a general definition of the amines to be used further as starting materials in the process according to the invention for the preparation of the compounds of the general formula (II).
  • a and X preferably or in particular have those meanings which are already preferred or particularly preferred in connection with the description of the compounds of the formula (I) or of the formula (II) were given for A and X.
  • the starting materials of the formula (IV) are known synthetic chemicals.
  • Position of the compounds of formula (I) and the compounds of formula (II) are the usual organic solvents. These 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, tetrachloromethane; 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 benzonit
  • the processes according to the invention for the preparation of the compounds of the formula (I) and of the compounds of the formula (II) are preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary Practically all conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide , Sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methyl
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention for the preparation of the compounds of the formula (I) and of the compounds of the formula (II). Generally works one at temperatures between 0 ° C and 200 ° C, preferably at temperatures between 20 ° C and 150 ° C.
  • reaction auxiliary 1 to 3 mol, preferably 1.0 to 2.0 mol, of reaction auxiliary are generally employed per mol of substituted carboxamide of the formula (II).
  • the substituted carboxamide of the formula (II), the reaction auxiliary and the diluent are mixed at room temperature and the mixture is - preferably at elevated temperature - until Stirred at the end of the implementation.
  • the workup can then be carried out using customary methods.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are carried out in a suitable diluent, if appropriate, but also in bulk, if appropriate in the presence of an acid acceptor, and the reaction mixture is for several hours - IS -
  • Formula (II) has a strong microbicidal action and can be used practically to control unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Pythium species such as Pythium ultimum:
  • Phytophthora species such as, for example, Phytophthora infestans
  • 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, 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 Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechs ⁇ lera, synonym: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as 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 fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds and of the soil.
  • the active compounds according to the invention can be particularly successful in combating diseases in fruit cultivation, for example against Podosphaera and Venturia species, for combating cereal diseases, for example against Erysiphe species or for combating diseases in rice cultivation, for example against Pyricularia oryzae can be used.
  • the active compounds according to the invention have a good action, for example against Cochliobolus sativus, Septoria nodorum and Phytophtora teres.
  • the active compounds can be converted into 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, under pressure the liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie 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
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromas such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, 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 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.
  • Solid carriers 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 suitable: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepio-lith, dolomite and 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 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 sulfon
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations. as well as natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. 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 are used.
  • 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 are 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 spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects occur.
  • Fungicides for the mixtures, for example: Fungicides:
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, tri-adimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflorolizol, triflorolizol, triflorolizole,
  • Chlorfluazuron Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexa-tin,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro-nil,
  • Fonophos Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M,, Primiphos A, Profenofos,
  • Tebufenozid Tebufenpyrad
  • Tebupirimphos Teflubenzuron
  • Tefluthrin Temephos
  • 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, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method 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 active substance concentrations in the use forms can be varied within a wide range: - 2 -
  • They are generally between 1 and 0.0001% by weight, preferably between. 0.5 and 0.001% by weight.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • Example 9 The compound listed in Table 1 as Example 9 can also be produced, for example, as follows:
  • Solvent 4.7 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
  • 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 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.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • 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 "test for protective activity, young plants are sprayed with the preparation of active compound until dripping wet. After the spray coating, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain for 1 day at 20 ° C and 100% relati ⁇ ver humidity in an incubation cabin.
  • the plants are then placed in a greenhouse at 20 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • 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.
  • Emulsifier 0.6 part by weight of alkylaryl polyglyko . lether
  • 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.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • 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.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • 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.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
  • the disease infestation is evaluated 4 days after the inoculation.

Abstract

L'invention concerne des oxazacycloalcènes substitués de la formule (I) dans laquelle A désigne alcandiyle (alkylène) éventuellement substitué, Ar désigne arylène ou hétéroarylène éventuellement substitué, E désigne un groupement 1-alcène-1, 1-diyle qui contient un reste R1 en position 2, ou un groupement 2-aza-1-alcène-1, 1-diyle qui contient un reste R2 en position 2, ou un groupement 3-aza-1-propène-2,3-diyle qui contient un reste R en position 3 et un reste R1 en position 1, ou un groupement 1-aza-1-propène-2,3-diyle qui contient un reste R2 en position 1, ou un groupement 1,3-diaza-1-propène-2,3-diyle qui contient un reste R en position 3 et un reste R2 en position 1, ou un groupement imino éventuellement substitué ('azaméthylène', N-R3), G désigne oxygène, alcandiyle éventuellement substitué par halogène, hydroxy, alkyle, halogénure d'alkyle ou cycloalkyle ou un des groupements suivants: -Q-CQ-, -CQ-Q-, -CH¿2?-Q-; -Q-CH2-, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2-, -C(R?4¿)=N-O-, -C(R4)=N-O-CH¿2?-, -N(R?5¿)-, -CQ-N(R5)-, -N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH2-, -CH¿2?-O-N=C(R?4¿)-, -N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH¿2?-, -CQ-CH2- ou -N=N-C(R?4¿)=N-O-; Z désigne alkyle, alcényle, alcinyle, cycloalkyle, aryle ou hétérocyclyle éventuellement substitué. L'invention concerne en outre un procédé et des produits intermédiaires permettant de les préparer, ainsi que l'utilisation d'oxazacycloalkènes comme fongicides.
EP95906997A 1994-02-11 1995-01-30 Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides Withdrawn EP0743941A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4404373 1994-02-11
DE4404373A DE4404373A1 (de) 1994-02-11 1994-02-11 Substituierte Oxazacycloalkene
PCT/EP1995/000311 WO1995021833A1 (fr) 1994-02-11 1995-01-30 Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides

Publications (1)

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EP0743941A1 true EP0743941A1 (fr) 1996-11-27

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EP95906997A Withdrawn EP0743941A1 (fr) 1994-02-11 1995-01-30 Oxazacycloalkenes substitues, produits intermediaires et utilisation comme fongicides

Country Status (6)

Country Link
EP (1) EP0743941A1 (fr)
JP (1) JPH09508634A (fr)
AU (1) AU1536795A (fr)
DE (1) DE4404373A1 (fr)
WO (1) WO1995021833A1 (fr)
ZA (1) ZA951092B (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6268312B1 (en) * 1994-04-01 2001-07-31 Shionogi & Co., Ltd. Oxime derivative and bactericide containing the same as active ingredient
CA2186947A1 (fr) * 1994-04-01 1995-10-12 Kazuo Ueda Derive d'oxime et bactericide le contenant en tant qu'ingredient actif

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
DE3161525D1 (en) * 1980-03-05 1984-01-05 Ciba Geigy Ag Herbicidally active 2-nitro-5-phenoxyphenyl oxazoles, oxazines, imidazoles, pyrimidines and thiazoles, their preparation and their use
ES2110421T5 (es) * 1990-06-27 2004-12-01 Basf Aktiengesellschaft O-bencil-oximeteres y los agentes protectores de las plantas que contienen estos compuestos.
DK0579124T3 (da) * 1992-07-15 1996-11-18 Basf Ag Substituerede oximethere, fremgangsmåde til deres fremstilling og deres anvendelse til bekæmpelse af skadelige organismer og svampe
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 WO9521833A1 *

Also Published As

Publication number Publication date
DE4404373A1 (de) 1995-08-17
AU1536795A (en) 1995-08-29
ZA951092B (en) 1995-10-13
WO1995021833A1 (fr) 1995-08-17
JPH09508634A (ja) 1997-09-02

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