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WO1996038424A1 - Cycloalcane-benzylides utilises comme microbicides - Google Patents

Cycloalcane-benzylides utilises comme microbicides

Info

Publication number
WO1996038424A1
WO1996038424A1 PCT/EP1996/002163 EP9602163W WO9638424A1 WO 1996038424 A1 WO1996038424 A1 WO 1996038424A1 EP 9602163 W EP9602163 W EP 9602163W WO 9638424 A1 WO9638424 A1 WO 9638424A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
butyl
cycloalkane
carbon atoms
metal salt
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.)
Ceased
Application number
PCT/EP1996/002163
Other languages
German (de)
English (en)
Inventor
Manfred Jautelat
Ralf Tiemann
Stefan Dutzmann
Klaus Stenzel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to AU59002/96A priority Critical patent/AU5900296A/en
Publication of WO1996038424A1 publication Critical patent/WO1996038424A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • A01N43/64—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
    • 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

Definitions

  • the present invention relates to new cycloalkane-benzylidene derivatives, a process for their preparation and their use as microbicides.
  • R 1 and R 2 independently of one another represent hydrogen or alkyl having 1 to 6 carbon atoms
  • R 3 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • n the numbers 0 or 1
  • n. represents the numbers 0, 1 or 2, as well as their acid addition salts and metal salt complexes.
  • 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 substances also contain an asymmetrically substituted C-C double bond; they can therefore also be obtained as E or Z isomers.
  • the present invention relates both to the individual isomers and to their mixtures.
  • R 1 , R 2 , X, m and n have the meanings given above,
  • R 1 , R 2 , X, m and n have the meanings given above, it halogen compounds of the formula
  • R 4 represents alkyl having 1 to 4 carbon atoms
  • Formula (I) and its acid addition salts and metal salt complexes have very good microbicidal properties and can be used in a protective manner both in crop protection and in the material.
  • the substances according to the invention have a better microbicidal activity than the structurally most similar, known compounds of the same action.
  • the substances according to the invention outperform 2- (4-chlorobenzylidene) -5,5-dimethyl-l- (1,2,4-triazol-l-ylmethyl) cyclopentan-ol in terms of their fungicidal properties.
  • Formula (I) provides a general definition of the cycloalkane-benzylidene derivatives according to the invention.
  • R 1 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl.
  • R 2 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl .. sec-butyl, tert-butyl or n-pentyl.
  • R 3 preferably represents hydrogen, methyl or ethyl.
  • X preferably represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, Difluoromethyl, trichloromethoxy, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or phenyl.
  • n also preferably represents the numbers 0 or 1.
  • n is also preferably the number 0, 1 or 2. If n is 2, X can be the same or different radicals.
  • Preferred substances according to the invention are also addition products of acids and those cycloalkane-benzylidene derivatives of the formula (I) in which R 1 , R 2 , R 3 , X, m and n have those meanings which are preferred for these substituents and these indices were called.
  • the acids that can be added preferably include hydrohalic acids, e.g. the hydrochloric acid and the hydrobromic acid, in particular the hydrochloric acid, also phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as 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. the hydrochloric acid and the hydrobromic acid, in particular the hydrochloric acid, also phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as e.g. Acetic acid
  • 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. As well as IV. To VIII where R 1 , R 2 , R 3 , X, m and n have those meanings which have been mentioned as preferred for these substituents and these indices.
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products.
  • Particularly preferred acids in this connection are the hydrogen halide acids, such as, for example, hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.
  • Formula (II) provides a general definition of the cycloalkanol derivatives required as starting materials when carrying out the process according to the invention.
  • R 1 , R 2 , X, m and n preferably have those meanings which have already been mentioned as preferred in connection with the description of the substances of the formula (I) according to the invention for these radicals and these indices.
  • cycloalkanol derivatives of the formula (II) are known or can be prepared by known processes (cf. EP-A 0 378 953).
  • Suitable bases for 'carrying out the first step of the process according to the invention are all customary for such reactions, strong alkali metal bases.
  • inert organic solvents customary for such reactions can be considered as diluents.
  • Ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane, preferably liquid ammonia or also strongly polar solvents such as dimethyl sulfoxide can preferably be used.
  • Sulfur is preferably used in the form of powder.
  • water is used in carrying out the first stage of the process according to the invention, if appropriate in the presence of an acid. All inorganic or organic acids customary for such reactions can be considered. Acetic acid, dilute sulfuric acid and dilute hydrochloric acid are preferably usable. However, it is also possible to carry out the hydrolysis with an aqueous ammonium chloride solution.
  • reaction temperatures can be varied within a certain range when carrying out the first stage of the process according to the invention. In general, temperatures between -70 ° C and + 20 ° C, preferably between -70 ° C and 0 ° C.
  • the procedure is generally under normal pressure.
  • halogen compounds required as reaction components in carrying out the process according to the invention in the second stage are generally defined by the formula (III).
  • R 4 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, and tertiary acetate, calcium acetate, calcium acetate, are preferably usable
  • DABCO diazabicyclooct
  • Suitable diluents for carrying out the second stage of the process according to the invention are all inert organic solvents which are customary for such reactions.
  • 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.
  • the 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.
  • 1 to 2 mol of halogen compound of the formula (III) and an equivalent amount or an excess of acid binder are generally employed per mol of cycloalkane-benzylidene derivative of the formula (Ia) on.
  • the processing takes place according to usual methods. In general, the procedure is such that aqueous base and a water-immiscible organic solvent are added to the reaction mixture, the organic phase is separated off, dried and concentrated.
  • the product obtained can, if appropriate, be freed from impurities which are still present by customary methods, for example by recrystallization.
  • cycloalkane-benzylidene derivatives of the formula (I) obtainable by the process according to the invention can be converted into acid addition salts or metal salt complexes.
  • the acid addition salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrogen chloride acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrogen chloride acid
  • the metal salt complexes of the compounds of the formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol and adding it to compounds of the formula (I).
  • Metal salt complexes can be isolated in a known manner, for example by filtering off, and optionally purified 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.
  • Fungicides are used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • 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
  • Drechslera (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 can be used very well against Venturia and Sphaerotheca. They also have a very good in-vitro effect.
  • 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 by microorganisms or can be decomposed.
  • 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 are microorganisms which can cause degradation or a change in the technical materials and called mucus organisms.
  • 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 versicolasium, aureuloma aureoboma, asureobure aureobasobloma such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.
  • Trichoderma such as Trichoderma viride
  • Escherichia such as Escherich
  • 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 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. 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.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • 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 as well as 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 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 polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations 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, broaden the range of products or prevent the development of resistance. In some cases, synergistic effects also occur.
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
  • Ethoprophos Etrimphos, Fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
  • Fipronil fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox,
  • Methamidophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • Promecarb Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • Tebufenozid Tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,
  • Triazophos triazuron, trichlorfon, triflumuron, trimethacarb,
  • 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 optimum amount of use can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of activity of the active substances to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or others are used Active ingredients to enlarge 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.
  • 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.

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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 a pour objet de nouveaux dérivés de cycloalcane-benzylides, de formule (I), dans laquelle R1 et R2 désignent, indépendamment l'un de l'autre, l'hydrogène ou un alkyle avec 1 à 6 atomes de carbone, R3 désigne l'hydrogène ou un alkyle avec 1 à 4 atomes de carbone, X désigne un halogène, un cyano, un nitro, un alkyle avec 1 à 4 atomes de carbone, un alcoxy de 1 à 4 atomes de carbone, un halogénure d'alkyle avec 1 à 4 atomes de carbone et avec 1 à 5 atomes d'halogène, un halogénure d'alcoxy avec 1 à 4 atomes de carbone et avec 1 à 5 atomes d'halogène ou un phényle, m est égal à 0 ou 1, n est égal à 0, 1 ou 2. L'invention concerne également les sels d'addition acides et les complexes de sels métalliques de ces dérivés, un procédé de fabrication de ces produits et leur utilisation comme microbicides pour la protection des végétaux et des matériaux.
PCT/EP1996/002163 1995-06-01 1996-05-20 Cycloalcane-benzylides utilises comme microbicides Ceased WO1996038424A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU59002/96A AU5900296A (en) 1995-06-01 1996-05-20 Cycloalkane benzylidines as microbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19520096A DE19520096A1 (de) 1995-06-01 1995-06-01 Cycloalkan-benzyliden-Derivate
DE19520096.9 1995-06-01

Publications (1)

Publication Number Publication Date
WO1996038424A1 true WO1996038424A1 (fr) 1996-12-05

Family

ID=7763406

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002163 Ceased WO1996038424A1 (fr) 1995-06-01 1996-05-20 Cycloalcane-benzylides utilises comme microbicides

Country Status (5)

Country Link
AU (1) AU5900296A (fr)
DE (1) DE19520096A1 (fr)
IL (1) IL118443A0 (fr)
WO (1) WO1996038424A1 (fr)
ZA (1) ZA964470B (fr)

Cited By (5)

* 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
EP2746256A1 (fr) * 2012-12-19 2014-06-25 Basf Se Composés triazolyles et imidazolyles fongicides
WO2014095249A1 (fr) * 2012-12-19 2014-06-26 Basf Se Composés d'imidazolyle et triazolyle fongicides

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19732033A1 (de) 1997-07-25 1999-01-28 Bayer Ag Triazolinthion-phosphorsäure-Derivate
WO2010149414A1 (fr) * 2009-04-24 2010-12-29 Basf Se Composés de 5-mercapto-[1,2,4]triazolylméthylcyclopentanol et leurs utilisations agricoles et pharmaceutiques
AR076430A1 (es) * 2009-04-24 2011-06-08 Basf Se Derivados de triazol como fungicidas en composiciones agricolas y su uso como antivirales y en el tratamiento del cancer e intermediarios para producirlos
WO2010122170A1 (fr) * 2009-04-24 2010-10-28 Basf Se Composés 5-mercapto-[1, 2, 4] triazolylméthyl-cyclopentanol et leurs applications agricoles et pharmaceutiques
TW201041513A (en) * 2009-04-24 2010-12-01 Basf Se Triazole compounds carrying a sulfur substituent I
AR076428A1 (es) * 2009-04-24 2011-06-08 Basf Se Compuestos de triazol que llevan un sustituyente de azufre iii

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Publication number Priority date Publication date Assignee Title
EP0378953A1 (fr) * 1988-12-29 1990-07-25 Rhone-Poulenc Agrochimie Benzylidène azolylméthylecycloalcane et utilisation comme fongicide
DE3941593A1 (de) * 1989-12-16 1991-06-20 Basf Ag Azolylmethylcycloalkanole
EP0433780A1 (fr) * 1989-12-16 1991-06-26 BASF Aktiengesellschaft Azolylméthylcycloalkanols substitués et fongicides les contenant
EP0565463A1 (fr) * 1992-04-08 1993-10-13 Rhone-Poulenc Agrochimie Dérivés triazole et imidazole fongicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0378953A1 (fr) * 1988-12-29 1990-07-25 Rhone-Poulenc Agrochimie Benzylidène azolylméthylecycloalcane et utilisation comme fongicide
DE3941593A1 (de) * 1989-12-16 1991-06-20 Basf Ag Azolylmethylcycloalkanole
EP0433780A1 (fr) * 1989-12-16 1991-06-26 BASF Aktiengesellschaft Azolylméthylcycloalkanols substitués et fongicides les contenant
EP0565463A1 (fr) * 1992-04-08 1993-10-13 Rhone-Poulenc Agrochimie Dérivés triazole et imidazole fongicides

Cited By (9)

* 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
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
EP2746256A1 (fr) * 2012-12-19 2014-06-25 Basf Se Composés triazolyles et imidazolyles fongicides
WO2014095249A1 (fr) * 2012-12-19 2014-06-26 Basf Se Composés d'imidazolyle et triazolyle fongicides

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IL118443A0 (en) 1996-09-12
ZA964470B (en) 1996-12-11
DE19520096A1 (de) 1996-12-05
AU5900296A (en) 1996-12-18

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