+

WO2004062361A2 - Composes spiraniques - Google Patents

Composes spiraniques Download PDF

Info

Publication number
WO2004062361A2
WO2004062361A2 PCT/EP2004/000016 EP2004000016W WO2004062361A2 WO 2004062361 A2 WO2004062361 A2 WO 2004062361A2 EP 2004000016 W EP2004000016 W EP 2004000016W WO 2004062361 A2 WO2004062361 A2 WO 2004062361A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
plants
species
methyl
compounds
Prior art date
Application number
PCT/EP2004/000016
Other languages
German (de)
English (en)
Other versions
WO2004062361A3 (fr
Inventor
Bernd-Wieland Krüger
Astrid Mauler-Machnik
Original Assignee
Bayer Cropscience Aktiengesellschaft
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 Cropscience Aktiengesellschaft filed Critical Bayer Cropscience Aktiengesellschaft
Publication of WO2004062361A2 publication Critical patent/WO2004062361A2/fr
Publication of WO2004062361A3 publication Critical patent/WO2004062361A3/fr

Links

Classifications

    • 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
    • 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
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to new spiro compounds, a process for their production and their use to control undesirable microorganisms.
  • R represents optionally substituted heterocyclyl
  • the new spiro compounds of the formula (I) have very good microbicidal properties and can be used both in crop protection and in material protection to combat unwanted microorganisms.
  • the substances according to the invention can not only be used for the direct control of undesired microorganisms, but also practice
  • the spiro compounds of the formula (I) according to the invention show a substantially better fungicidal activity than the most similarly known, previously known active compounds of the same action.
  • the spiro compounds according to the invention are generally defined by the formula (I).
  • Preferred substances of the formula (I) are those in which
  • R represents optionally substituted by halogen and / or alkyl having 1 to 4 carbon atoms, optionally benzo-fused, five or six-membered heterocyclyl,
  • R is a radical of the formula which is halogen and / or
  • Alkyl with 1 to 4 carbon atoms can be substituted.
  • R represents single to triple, identical or different, pyridyl, isothiazolyl, thienyl or benzothiophenyl substituted by chlorine, bromine and / or methyl or
  • R stands for the rest of the formula, single or double can be substituted by chlorine, bromine and / or methyl.
  • Formula (II) provides a general definition of the acylaminocyclopropanecarboxylic acids required as starting materials for carrying out process (a) according to the invention.
  • 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.
  • acyla inocyclopropanecarboxylic acids of the formula (II) are hitherto unknown. They can be made by
  • R 1 represents methyl or ethyl, with water in the presence of a base and optionally in the presence of an organic diluent.
  • Formula (III) provides a general definition of the acylamino-cyclopropane-carboxylic acid esters required as starting substances for carrying out process (b).
  • 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.
  • R 1 represents methyl or ethyl.
  • acylamino-cyclopropanecarboxylic acid esters of the formula (III) are also not yet known. They can be made by
  • R 1 has the meanings given above, or their hydrohalides or hydrogen sulfates,
  • Formula (IV) provides a general definition of the aminocyclopropane-carboxylic acid esters required as starting substances for carrying out process (c).
  • R 1 represents methyl or ethyl.
  • aminocyclopropane-carboxylic acid esters of the formula (IV) are known or can be prepared by known methods (cf. DE-A 28 24 517, WO 86-03 378, EP-A 0 199 257 and Plant Growth Regul. 8 (4), (1989), 297-307). So let yourself be produce by reacting 1-amino-cyclopropane-carboxylic acid with methanol or ethanol in the presence of tliionyl chloride.
  • Formula (N) provides a general definition of the acid halogens required as reaction components for carrying out process (c). In this
  • Formula 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.
  • X preferably represents chlorine or bromine.
  • Suitable diluents for carrying out process (a) according to the invention are all customary, inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acet
  • Suitable condensation agents for carrying out process (a) according to the invention are all cyclization reagents which can normally be used for amidation reactions.
  • Acid halide formers can preferably be used such as phosgene, oxalyl chloride, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride;
  • Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride;
  • Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydr
  • Suitable acid binders for carrying out process (a) according to the invention are all customary inorganic and organic bases.
  • 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, are preferably usable.
  • ammonium compounds such as ammonium hydroxide, ammonium acetate or ammonium carbonate
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, N,
  • Suitable catalysts for carrying out process (a) according to the invention are all reaction accelerators customary for such reactions. Examples include 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. Generally works one at temperatures between -78 ° C and + 120 ° C, preferably at temperatures between -60 ° C and + 25 ° C.
  • Atmospheric pressure is also possible to work under increased or reduced pressure.
  • Bases which can be used in carrying out process (b) are all customary inorganic bases.
  • Alkaline earth metal or alkali metal hydroxides such as, for example, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, can preferably be used.
  • Suitable diluents for carrying out process (b) are all customary, water-miscible, organic solvents.
  • Alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether are preferably usable.
  • reaction temperatures can be varied within a substantial range when carrying out process (b). In general, temperatures from 0 ° C to 80 ° C, preferably at temperatures from 0 ° C to 50 ° C.
  • Suitable diluents for carrying out process (c) are all customary, inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as, for example, 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,
  • Suitable acid binders when carrying out process (c) are all customary inorganic and organic bases.
  • Potassium hydroxide sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or cesium carbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium carbonate or ammonium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimin , N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylamino-pyridine, diazabipyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclonecene (DBU).
  • the reaction temperatures can be varied within a substantial range when carrying out process (c). In general, temperatures from 0 ° C to 120 ° C, preferably at temperatures from 0 ° C to
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
  • 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 Pseudoperonospora cubensis;
  • 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 Sportsiginea;
  • 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 (conidial form: Drechslera, Syn: Helminthosporium);
  • 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 he ⁇ otrichoides.
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to protect plants from attack by the named pathogens within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
  • Concentrations necessary for plant diseases allow the treatment of above-ground parts of plants, of seedlings, and of the soil.
  • the active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe 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 active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be used.
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication 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 active compounds according to the invention preferably act against fungi, in particular molds, wood-coloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are 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, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Solid carriers are possible: e.g. 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.
  • Solid carriers for granules are possible: e.g.
  • nonionic and anionic emulsifiers such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as guariarabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used.
  • 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 to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • 2-phenylphenol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos potasium; andoprim; anilazine; azaconazole; azoxystrobin;
  • Dagger G debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; Dimethomo ⁇ h; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; Diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon;
  • edifenphos epoxiconazole; ethaboxam; ethirimol; etridiazole;
  • famoxadone fenamidone; Fenapanil; fenarimol; Fenbuconazole; Fenfiiram; Fenhexamide; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; Fenpropimo ⁇ h; ferbam;
  • fluazinam Flubenzimine; fludioxonil; flumetover; Flumo ⁇ h; fluoromides;
  • fluoxastrobin fluquinconazole; Flu ⁇ rimidol; flusilazole; flusulfamide; flutolanil;
  • flutriafol flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox;
  • mancozeb maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline;
  • natamycin natamycin
  • nicobifen Nitro Thal-isopropyl
  • Noviflumuron nuarimol
  • Thicyofen Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide;
  • Tricyclamide Tricyclazole; Tridemo ⁇ h; trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole;
  • sodium tetrathiocarbonate as well as copper salts and preparations, such as Bordeaux mixture; copper; copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Oxine-copper.
  • BTG-504 BTG-505, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butoxycarboxim, Butylpyridaben,
  • Chloroethoxyfos chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, Chlorobenzilate, Chloropicrin, Chlo ⁇ roxyfen, Chlo ⁇ yrifos-methyl, Chlo ⁇ yrifos (- ethyl), Chlovaporthrin, Chromafenozide, Cis-Cypermethrin, Cis-Resmethrin, Cis- Permethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophosphos, Cyanosophone, Clothianidin, Clothianidin, Clothianidin, Clothianidin, Clothianidin, Clothianidine, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyphenothrin
  • DDT Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimethoate, Dimethylvinphos, Dinobutonef, Dinobuton, Dinobuton
  • Halofenozide HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene,
  • Mecarbam Malathion, Mecarbam, Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb,
  • Metoxadiazone Mevinphos, Milbemectin, Milbemycin, MKI-245, MON-45700, Monocrotophos, Moxidectin, MTI-800,
  • NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
  • Paecilomyces fumosoroseus Parathion-methyl, Parathion (-ethyl), Permethrin (eis, trans-), Petroleum, PH-6045, Phenothrin (lR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos, propargite, propetamphos, propoxur, prothiofos, prothoate, protrifen-bute, pymetrozine, pyraclofos, pyreshridium pyrin, pyreshridium pyridhridium, pyreshridium pyridhridium, pyreshridium pyrin , Pyrimidifen
  • Teframethrin Teframethrin (IR-isomer), Tefrasul, Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringadhrinehrin, Thuringadhrininin , Triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal effects, especially against dermatophytes and sprout fungi, squid and diphasic fungi (e.g. against Candida species such as Candida albicans,
  • Candida glabrata and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi in no way represents a restriction of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated.
  • plant species and plant cultivars which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, and parts thereof are treated.
  • transgenic plants and plant cultivars which may be obtained by genetic engineering methods are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the
  • transgenic plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material which contains them
  • traits are better plant growth, increased tolerance to over high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and
  • Fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, with particular emphasis on corn, soybeans, potatoes, cotton, tobacco and rapeseed.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins that arise in the plants, especially those that are caused by the genetic material from BaciUus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Properties are also the increased defense of plants against fungi, bacteria and viruses is particularly emphasized
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active ingredients or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the plants are treated with spores of Erysiphe graminis f. sp. hordei pollinated.
  • the plants are then placed in a greenhouse at a temperature of approximately 20 ° C. and a relative atmospheric humidity of approximately 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des composés spiraniques représentés par la formule (I) dans laquelle R est hétérocyclyl éventuellement substitué, un procédé de fabrication de ces agents actifs et leur utilisation en tant que microbicides.
PCT/EP2004/000016 2003-01-16 2004-01-05 Composes spiraniques WO2004062361A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2003101419 DE10301419A1 (de) 2003-01-16 2003-01-16 Spiroverbindungen
DE10301419.5 2003-01-16

Publications (2)

Publication Number Publication Date
WO2004062361A2 true WO2004062361A2 (fr) 2004-07-29
WO2004062361A3 WO2004062361A3 (fr) 2005-08-18

Family

ID=32602599

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/000016 WO2004062361A2 (fr) 2003-01-16 2004-01-05 Composes spiraniques

Country Status (2)

Country Link
DE (1) DE10301419A1 (fr)
WO (1) WO2004062361A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007537180A (ja) * 2004-05-13 2007-12-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規置換チオフェンカルボキサミド、それらの調製方法及び薬物としてのそれらの使用
WO2020007905A1 (fr) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
WO2021001331A1 (fr) * 2019-07-03 2021-01-07 Bayer Aktiengesellschaft Thiophène carboxamides substitués et leurs dérivés comme microbicides
WO2021122986A1 (fr) 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thiényloxazolones et analogues
RU2831013C1 (ru) * 2019-12-20 2024-11-28 Байер Акциенгезельшафт Тиенилоксазолоны и аналоги

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4011172A1 (de) * 1990-04-06 1991-10-10 Degussa Verbindungen zur bekaempfung von pflanzenkrankheiten
JPH06228101A (ja) * 1993-01-29 1994-08-16 Ube Ind Ltd イソニコチン酸アミド誘導体、その製法及び農園芸用病害防除剤

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007537180A (ja) * 2004-05-13 2007-12-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規置換チオフェンカルボキサミド、それらの調製方法及び薬物としてのそれらの使用
US11401254B2 (en) 2018-07-05 2022-08-02 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
TWI831801B (zh) * 2018-07-05 2024-02-11 德商拜耳廠股份有限公司 經取代之噻吩甲醯胺及類似物
CN112601744A (zh) * 2018-07-05 2021-04-02 拜耳公司 作为抗菌剂的取代的噻吩甲酰胺及类似物
CN112638893A (zh) * 2018-07-05 2021-04-09 拜耳公司 作为抗菌剂的取代的噻吩甲酰胺及类似物
AU2019297402B2 (en) * 2018-07-05 2024-05-02 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
JP2021530452A (ja) * 2018-07-05 2021-11-11 バイエル・アクチエンゲゼルシヤフト 抗菌剤としての置換チオフェンカルボキサミド類及び類縁体
JP7476118B2 (ja) 2018-07-05 2024-04-30 バイエル・アクチエンゲゼルシヤフト 抗菌剤としての置換チオフェンカルボキサミド類及び類縁体
WO2020007905A1 (fr) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
US11952359B2 (en) 2018-07-05 2024-04-09 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
CN112601744B (zh) * 2018-07-05 2024-03-29 拜耳公司 作为抗菌剂的取代的噻吩甲酰胺及类似物
US11884643B2 (en) 2018-07-05 2024-01-30 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
WO2021001331A1 (fr) * 2019-07-03 2021-01-07 Bayer Aktiengesellschaft Thiophène carboxamides substitués et leurs dérivés comme microbicides
CN114364663A (zh) * 2019-07-03 2022-04-15 拜耳公司 作为杀微生物剂的取代的噻吩甲酰胺及其衍生物
RU2834236C2 (ru) * 2019-07-03 2025-02-04 Байер Акциенгезельшафт Замещенные тиофенкарбоксамиды и их производные
CN115038698A (zh) * 2019-12-20 2022-09-09 拜耳公司 噻吩基噁唑酮及类似物
WO2021122986A1 (fr) 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thiényloxazolones et analogues
RU2831013C1 (ru) * 2019-12-20 2024-11-28 Байер Акциенгезельшафт Тиенилоксазолоны и аналоги
TWI870523B (zh) * 2019-12-20 2025-01-21 德商拜耳廠股份有限公司 噻吩基唑啉酮及類似物

Also Published As

Publication number Publication date
DE10301419A1 (de) 2004-07-29
WO2004062361A3 (fr) 2005-08-18

Similar Documents

Publication Publication Date Title
EP1490342B1 (fr) Carboxanilides de pyrazolyle disubstitues
EP1590330B1 (fr) Pyrazolylcarboxanilides pour lutter contre des micro-organismes indesirables
WO2004103975A1 (fr) Iodopyrazolylcarboxanilides
EP2192115B1 (fr) 1,3-diméthylbutylcarboxanilides pour contrôler des micro-organismes indésirables
DE10325133A1 (de) Triazolopyrimidine
EP1558592B1 (fr) Thiazol-(bi)cycloalkylcarboxanilides
EP1680407A1 (fr) Isopentylcarboxanilides pour lutter contre des micro-organismes indesirables
DE10360369A1 (de) Amide
EP1480516B1 (fr) Agents microbicides a base de derives de biphenyle benzamide
EP1687315B1 (fr) Carboxamides silyles
EP1678143B1 (fr) Pyrazolylcarboxanilides n-substitues
EP1551816B1 (fr) Amides thiazolyle biphenyle
WO2003093223A1 (fr) Biphényles carboxamides
DE102004012901A1 (de) Silylierte Carboxamide
EP1599460A2 (fr) Oxathiine-carboxamides
EP1501820B1 (fr) Methylthiophenocarboxa nilides
WO2004103953A1 (fr) Difluoromethylbenzanilides, leur utilisation pour lutter contre des micro-organismes, produits intermediaires et production de ceux-ci
DE10357569A1 (de) Pyrazolopyrimidine
DE10357568A1 (de) Pyrazolopyrimidine
DE10352067A1 (de) Isopentylcarboxanilide
DE10357567A1 (de) Pyrazolopyrimidine
WO2004062361A2 (fr) Composes spiraniques
DE102004007076A1 (de) Imidazolopyrimidine
DE10357565A1 (de) Pyrazolopyrimidine
DE10357566A1 (de) Pyrazolopyrimidine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
DPEN Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101)
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载