WO1997006151A1 - Mercapto-triazolyl-cetones microbicides - Google Patents

Mercapto-triazolyl-cetones microbicides Download PDF

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Publication number
WO1997006151A1
WO1997006151A1 PCT/EP1996/003335 EP9603335W WO9706151A1 WO 1997006151 A1 WO1997006151 A1 WO 1997006151A1 EP 9603335 W EP9603335 W EP 9603335W WO 9706151 A1 WO9706151 A1 WO 9706151A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
formula
triazolyl
halogen
mercapto
Prior art date
Application number
PCT/EP1996/003335
Other languages
German (de)
English (en)
Inventor
Manfred Jautelat
Ralf Tiemann
Stefan Dutzmann
Klaus Stenzel
Original Assignee
Bayer 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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU67387/96A priority Critical patent/AU6738796A/en
Priority to EP96927624A priority patent/EP0843668A1/fr
Priority to JP9508087A priority patent/JPH11510799A/ja
Publication of WO1997006151A1 publication Critical patent/WO1997006151A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to new mercapto-triazolyl ketones, a process for their preparation and their use as microbicides.
  • R 1 for alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 4
  • Carbon atoms and 1 to 5 halogen atoms optionally substituted by halogen and / or alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part, optionally by halogen substituted phenyl or benzyl optionally substituted by halogen,
  • R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • X represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4
  • n 0, 1, 2 or 3
  • Y represents an oxygen atom or a CH 2 group
  • the substances according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be obtained in the form of enantiomers.
  • the present invention relates both to the individual isomers and to their mixtures.
  • R 1 , X, Y and m have the meanings given above,
  • R 1 , X, Y and m have the meanings given above,
  • R 3 represents alkyl having 1 to 4 carbon atoms
  • Material can be used in a protective manner.
  • the substances according to the invention have a better microbicidal activity than the constitutionally most similar, known compounds of the same direction of action.
  • the substances according to the invention outperform l- (4-chlorophenoxy) -l- (1,2,4-triazol-l-yl) -3,3-dimethylbutan-2-one in terms of their fungicidal properties.
  • the mercapto-triazolyl-ketones according to the invention are generally defined by the formula (I).
  • R 1 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine atoms, optionally monosubstituted to trisubstituted, similarly or differently, by fluorine, chlorine, bromine, methyl and / or ethyl Cycloalkyl with 3 to 6 carbon atoms, cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 to 3 carbon atoms in the alkyl part, optionally single to triple, identical or different phenyl substituted by fluorine, chlorine and / or bromine or for optionally single to triple, similar or benzyl substituted differently by fluorine, chlorine and / or bromine.
  • R 2 preferably represents hydrogen, methyl or ethyl.
  • X preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,
  • n also preferably represents the numbers 0, 1, 2 or 3, where X represents the same or different radicals if m represents 2 or 3.
  • Y also preferably represents an oxygen atom or a CH 2 group.
  • R 1 particularly preferably represents methyl, isopropyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, optionally single to triple, identical or different, cyclopropyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine and / or methyl , for cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part, optionally mono- or disubstituted, identical or different phenyl substituted by fluorine, chlorine and / or bromine or for optionally single or double, identical or different benzyl substituted by fluorine, chlorine and / or bromine.
  • R 2 also particularly preferably represents hydrogen, methyl or ethyl.
  • X particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy.
  • Y also particularly preferably represents an oxygen atom or a CH 2 group.
  • n also particularly preferably represents the numbers 0, 1, 2 or 3, where X represents the same or different radicals if m represents 2 or 3.
  • Preferred compounds according to the invention are also addition products of acids and those mercapto-triazolyl-ketones of the formula (I) in which R 1 , R 2 , X, Y and m have those meanings which have been mentioned as preferred for these substituents and this index.
  • the acids that can be added preferably include hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids, e.g. p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid, or camphorsulfonic acid, saccharin and thiosaccharin.
  • hydrohalic acids e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic acid, succinic acid, fuma
  • preferred compounds according to the invention are addition products from salts of metals of the II. To IV. Main group and of I. and II. And IV. To VIII. Subgroup of the periodic table of the elements and those mercapto-triazolyl-ketones of the formula (I), in those R 1 , R 2 , X, Y and m have those meanings which have been mentioned as preferred for these radicals and this index.
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts come in Consideration which are derived from those acids which lead to physiologically tolerable addition products.
  • Particularly preferred acids in this connection are the hydrohalic acids, such as hydrochloric acid and hydrobromic acid, furthermore phosphoric acid, nitric acid and sulfuric acid.
  • Formula (II) provides a general definition of the triazolyl ketones required as starting materials when carrying out the process according to the invention.
  • R 1 , X, Y and m preferably have those meanings which have already been mentioned as preferred for these radicals and this index in connection with the description of the substances of the formula (I) according to the invention.
  • the triazolyl ketones of the formula (II) are known or can be prepared by known processes (cf. DE-A 2 201 063 and DE-A 2 737 489).
  • Amides such as dimethylformamide and dimethylacetamide, also heterocyclic compounds, such as N-methyl-pyrrolidone, and also ethers, such as diphenyl ether.
  • heterocyclic compounds such as N-methyl-pyrrolidone
  • ethers such as diphenyl ether
  • Sulfur is generally used in the form of powder when carrying out the first stage of the process according to the invention.
  • the reaction can be carried out under a protective gas atmosphere, for example under nitrogen or argon.
  • treatment with water and, if appropriate, with acid can optionally be carried out.
  • All the usual inorganic or organic acids suitable for hydrolysis come into question.
  • Acetic acid, dilute sulfuric acid and dilute hydrochloric acid are preferably usable.
  • reaction temperatures can be varied within a substantial range when carrying out the first stage of the process according to the invention. In general, temperatures between 150 ° C and 300 ° C, preferably between 180 ° C and 250 ° C.
  • the procedure is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure. Working under increased pressure is particularly important when carrying out the first stage.
  • the compounds of the formula (Ia) required as starting substances when carrying out the second stage of the process according to the invention are substances according to the invention.
  • Formula (III) provides a general definition of the halogen compounds required as reaction components in carrying out the process according to the invention in the second stage.
  • R 3 preferably represents methyl or ethyl.
  • Shark also preferably represents chlorine, bromine or iodine.
  • Suitable acid binders for carrying out the second stage of the process according to the invention are all customary inorganic or organic bases.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, aminate, and trimethyl acetate, as well as terti
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, aminate, and trimethyl acetate, as well as terti
  • Suitable diluents for carrying out the second stage of the process according to the invention are all inert, customary for such reactions organic solvents.
  • Ethers such as diethyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, furthermore nitriles such as acetonitrile and also strongly polar solvents such as dimethyl sulfoxide or dimethylformamide can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out the second stage of the process according to the invention. In general, temperatures between 0 ° C and 120 ° C, preferably between 20 ° C and 100 ° C.
  • the product can be prepared by customary methods, e.g. by recrystallization, from any impurities still present.
  • the mercapto-triazolyl ketones of the formula (I) obtainable by the process according to the invention can be converted into acid addition salts or metal salt complexes.
  • Be obtained by conventional salt formation methods for example by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, for example hydrochloric acid, and in a known manner, for example by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • the metal salt complexes of the compounds of formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol and adding to compounds of formula (I).
  • Metal salt complexes can be prepared in a known manner, e.g. by filtering, isolating and, if necessary, cleaning by recrystallization.
  • the active compounds according to the invention have a strong microbicidal action and can be used to protect against undesirable microorganisms, such as fungi and bacteria, in crop protection and in the material.
  • the undesirable microorganisms include fungi, such as Piasmodi ophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidio-mycetes, Deuteromycetes, and also bacteria, such as Pseudomonadaceae, Rhizobiaceae, Enterobateriaceae and Corynebacteriaceae.
  • fungi such as Piasmodi ophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidio-mycetes, Deuteromycetes
  • bacteria such as Pseudomonadaceae, Rhizobiaceae, Enterobateriaceae and Corynebacteriaceae.
  • Xanthomonas species such as Xanthomonas oryzae
  • Pseudomonas species such as Pseudomonas lachrymans
  • Erwinia species such as Erwinia amylovora
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis: Plasmopara species, such as Plasmopara viticola;
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Podosphaera species such as Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as Pyrenophora teres or P. graminea;
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as Cochliobolus sativus; (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as Uromyces appendiculatus
  • Puccinia species such as Puccinia recondita
  • Tilletia species such as Tilletia caries
  • Ustilago species such as Ustilago nuda or Ustilago avenae
  • Pellicularia species such as Pellicularia sasakii
  • Pyricularia species such as Pyricularia oryzae
  • Fusarium species such as Fusarium culmorum
  • Botrytis species such as Botrytis cinerea
  • Septoria species such as Septoria nodorum
  • Leptosphaeria species such as Leptosphaeria nodorum
  • Cercospora species such as Cercospora canescens
  • Alternaria species such as Alternaria brassicae
  • Pseudocercosporella species such as Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention are particularly suitable for controlling Pyricularia oryzae and Pellicularia sasakii on rice and for controlling cereal diseases such as Pseudocercosporella, Erysiphe and Fusarium species.
  • the substances according to the invention are very good against Venturia and
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be.
  • parts of production plants for example cooling water circuits, may also be 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 mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium 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 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 fog 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 Means. If water is used as an extender, organic solvents such as alcohols 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 Means.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents Means.
  • organic solvents such as alcohols can also be used as auxiliary solvents.
  • liquid 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, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide; Solid carrier materials are suitable: for example natural rock powders such
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and 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 can be used.
  • the formulations In crop protection, 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 be used in the formulations 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.
  • Fludioxonil fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole,
  • Imazalil Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan, Kasugamycin
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Mepan Mepronil, metalaxyl, metconazole,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, fluazinam, flucycloxuron, flucythrinat, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazat, fubfenprox, furathiocarb, hch, heptenophos, hexaflumuron, hexythiazox, imidacloprid, isofoshrinophone, isofoshrinophosphorosinoxin, isofoshroxin, isofoxin, iodosfosofin, isofoxin, isphosphonosinoxin, isfoshroxin, isotrophin, isfo
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Py
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temephos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralathenethrin, Triarathenethrin
  • Triazophos Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, Zetamethrin.
  • 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 customary manner, for example 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 prepare the active ingredient or the like Inject active ingredient into the soil yourself.
  • the seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range: 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.
  • the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
  • the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimal amount of use can be determined by test series.
  • the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of action of the active ingredients to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or others are used Active ingredients to increase the spectrum of activity or to achieve special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • Methylpyrrolidone is heated to 200 ° C. for 8 hours under a nitrogen atmosphere and with stirring. The reaction mixture is then concentrated under reduced pressure and the remaining residue is dissolved in dichloromethane. The resulting mixture is shaken out several times with saturated, aqueous ammonium chloride solution.
  • Emulsifier 0.6 part by weight of alkyl aryl 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 sprayed with a conidia suspension of Cochliobolus sativus.
  • the plants remain at 20 ° C and 100 ° C rel. 48 hours. Humidity in an incubation cabin.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouvelles mercapto-triazolyl-cétones de formule (I), dans laquelle R1, R2, X, Y et m ont la signification donnée dans la description, leurs sels d'addition d'acide et leurs complexes avec des sels métalliques, ainsi que leur procédé de préparation et leur utilisation comme microbicides phytosanitaires et de protection de matériaux.
PCT/EP1996/003335 1995-08-08 1996-07-29 Mercapto-triazolyl-cetones microbicides WO1997006151A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU67387/96A AU6738796A (en) 1995-08-08 1996-07-29 Microbicidal mercapto-triazolyl-ketones
EP96927624A EP0843668A1 (fr) 1995-08-08 1996-07-29 Mercapto-triazolyl-cetones microbicides
JP9508087A JPH11510799A (ja) 1995-08-08 1996-07-29 殺微生物性メルカプト−トリアゾリル−ケトン

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19529091.7 1995-08-08
DE1995129091 DE19529091A1 (de) 1995-08-08 1995-08-08 Mercapto-triazolyl-ketone

Publications (1)

Publication Number Publication Date
WO1997006151A1 true WO1997006151A1 (fr) 1997-02-20

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PCT/EP1996/003335 WO1997006151A1 (fr) 1995-08-08 1996-07-29 Mercapto-triazolyl-cetones microbicides

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EP (1) EP0843668A1 (fr)
JP (1) JPH11510799A (fr)
AU (1) AU6738796A (fr)
DE (1) DE19529091A1 (fr)
WO (1) WO1997006151A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997041107A1 (fr) * 1996-04-30 1997-11-06 Bayer Aktiengesellschaft Triazolyl-mercaptides et leur utilisation comme microbicides
WO1997042178A1 (fr) * 1996-05-02 1997-11-13 Bayer Aktiengesellschaft Derives d'acylmercapto-triazolyle et leur utilisation comme microbicides
WO1997044331A1 (fr) * 1996-05-21 1997-11-27 Bayer Aktiengesellschaft Derives de thiocyano-triazolyle et leur utilisation comme microbicides
WO2010040718A1 (fr) * 2008-10-07 2010-04-15 Basf Se Composés triazole et imidazole, leur utilisation et agents les contenant
WO2010040717A1 (fr) * 2008-10-07 2010-04-15 Basf Se Composés triazole et imidazole, leur utilisation et agents les contenant
WO2011069912A1 (fr) 2009-12-07 2011-06-16 Basf Se Composés triazole, leur utilisation et produits les contenant
WO2011069916A1 (fr) 2009-12-08 2011-06-16 Basf Se Composés triazoles, leur utilisation comme fongicides et agents les contenant
WO2011069894A1 (fr) 2009-12-08 2011-06-16 Basf Se Composés triazoles, leur utilisation et agents les contenant
WO2011073145A1 (fr) 2009-12-18 2011-06-23 Basf Se Procédé de préparation de dérivés de triazolinethiones et intermédiaires de ces composés
WO2011113820A1 (fr) 2010-03-16 2011-09-22 Basf Se Procédé utilisant des réactifs de grignard
WO2012041858A1 (fr) 2010-09-30 2012-04-05 Basf Se Procédé de synthèse de composés contenant des groupes thio-triazolo
WO2012146598A1 (fr) 2011-04-28 2012-11-01 Basf Se Procédé de préparation de 4-amino-2,4-dihydro-[1,2,4]triazole-3-thiones 2-substituées
WO2012146535A1 (fr) 2011-04-28 2012-11-01 Basf Se Procédé pour la préparation de 2,4-dihydro-[1,2,4]triazole-3-thiones 2-substituées

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WO1997041107A1 (fr) * 1996-04-30 1997-11-06 Bayer Aktiengesellschaft Triazolyl-mercaptides et leur utilisation comme microbicides
US6057353A (en) * 1996-04-30 2000-05-02 Bayer Aktiengesellschaft Triazolyl-mercaptides and their use as microbicides
WO1997042178A1 (fr) * 1996-05-02 1997-11-13 Bayer Aktiengesellschaft Derives d'acylmercapto-triazolyle et leur utilisation comme microbicides
US6051592A (en) * 1996-05-02 2000-04-18 Bayer Aktiengesellschaft Acyl-mercapto-triazolyl derivatives and the use thereof as microbicides
US6274610B1 (en) 1996-05-02 2001-08-14 Bayer Aktiengesellschaft Acyl mercapto-triazolyl derivatives and the use thereof as microbicides
WO1997044331A1 (fr) * 1996-05-21 1997-11-27 Bayer Aktiengesellschaft Derives de thiocyano-triazolyle et leur utilisation comme microbicides
US6166059A (en) * 1996-05-21 2000-12-26 Bayer Aktiengesellschaft Thiocyano- triazolyl derivatives and their use as microbicides
WO2010040717A1 (fr) * 2008-10-07 2010-04-15 Basf Se Composés triazole et imidazole, leur utilisation et agents les contenant
WO2010040718A1 (fr) * 2008-10-07 2010-04-15 Basf Se Composés triazole et imidazole, leur utilisation et agents les contenant
WO2011069912A1 (fr) 2009-12-07 2011-06-16 Basf Se Composés triazole, leur utilisation et produits les contenant
WO2011069916A1 (fr) 2009-12-08 2011-06-16 Basf Se Composés triazoles, leur utilisation comme fongicides et agents les contenant
WO2011069894A1 (fr) 2009-12-08 2011-06-16 Basf Se Composés triazoles, leur utilisation et agents les contenant
WO2011073145A1 (fr) 2009-12-18 2011-06-23 Basf Se Procédé de préparation de dérivés de triazolinethiones et intermédiaires de ces composés
WO2011113820A1 (fr) 2010-03-16 2011-09-22 Basf Se Procédé utilisant des réactifs de grignard
WO2012041858A1 (fr) 2010-09-30 2012-04-05 Basf Se Procédé de synthèse de composés contenant des groupes thio-triazolo
WO2012146598A1 (fr) 2011-04-28 2012-11-01 Basf Se Procédé de préparation de 4-amino-2,4-dihydro-[1,2,4]triazole-3-thiones 2-substituées
WO2012146535A1 (fr) 2011-04-28 2012-11-01 Basf Se Procédé pour la préparation de 2,4-dihydro-[1,2,4]triazole-3-thiones 2-substituées

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AU6738796A (en) 1997-03-05
EP0843668A1 (fr) 1998-05-27
JPH11510799A (ja) 1999-09-21

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