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WO1996036634A1 - Oxyranyle-hydroyethyle-atriazoles - Google Patents

Oxyranyle-hydroyethyle-atriazoles Download PDF

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Publication number
WO1996036634A1
WO1996036634A1 PCT/EP1996/001820 EP9601820W WO9636634A1 WO 1996036634 A1 WO1996036634 A1 WO 1996036634A1 EP 9601820 W EP9601820 W EP 9601820W WO 9636634 A1 WO9636634 A1 WO 9636634A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
oxiranyl
hydroxyethyl
carbon atoms
triazoles
Prior art date
Application number
PCT/EP1996/001820
Other languages
German (de)
English (en)
Inventor
Michael Lindemann
Stefan Dutzmann
Gerd Hänssler
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 AU58123/96A priority Critical patent/AU5812396A/en
Publication of WO1996036634A1 publication Critical patent/WO1996036634A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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

Definitions

  • the present invention relates to new oxiranyl-hydroxyethyl-triazoles, a process for their preparation and their use as microbicides.
  • X represents hydrogen, halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms,
  • Z represents halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to
  • n 0, 1, 2 or 3
  • the substances according to the invention contain two asymmetrically substituted carbon atoms. They can therefore be obtained in the form of diastereomers or optical isomers.
  • the present invention relates both to the individual isomers and to their mixtures.
  • 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 thus exceed the 3.3-
  • X preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl,
  • Z preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, methoxy, Ethoxy, trifluoromethoxy, difluoromethoxy, nitro or for phenyl which is optionally mono- or disubstituted, identical or different, by fluorine and / or chlorine.
  • n preferably represents the numbers 0, 1, 2 or 3. If m represents 2 or 3, Z can represent the same or different radicals.
  • Preferred substances according to the invention are also addition products of acids and those oxiranyl-hydroxyethyl-triazoles of the formula (I) in which X, Z and m have the meanings given as preferred.
  • the acids that can be added preferably include hydrohalic acids, e.g. the hydrochloric acid and the hydrobromic acid, in particular the hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric 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-
  • hydrohalic acids e.g. the hydrochloric acid and the hydrobromic acid, in particular the hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric 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
  • Toluenesulfonic acid 1,5-naphthalenedisulfonic acid, camphorsulfonic acid, saccharin and thiosaccharin.
  • 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 oxiranyl-hydroxyethyl-triazoles of the formula (I), in which X, Z and m have the meanings given as preferred.
  • 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 are too physiologically compatible Lead addition products.
  • Particularly preferred acids in this context are the hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, furthermore phosphoric acid, nitric acid and sulfuric acid.
  • oxiranyl-hydroxyethyl-triazoles of the formula (I) are the substances listed in the table below.
  • Formula (II) provides a general definition of the triazolyl-butenols required as starting materials when carrying out the process according to the invention.
  • X, Z and m preferably have those meanings which have already been mentioned preferably in connection with the description of the substances of the formula (I) according to the invention for these radicals or this index.
  • the triazolyl-butenols of the formula (II) are known or can be prepared by methods known in principle (cf. DE-A 4 419 812).
  • Suitable reaction components when carrying out the process according to the invention are all peracids customary for such reactions.
  • Suitable diluents for carrying out the process according to the invention are all inert organic solvents which are customary for such reactions.
  • Halogenated aliphatic hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, and also aliphatic carboxylic acids, such as acetic acid or glacial acetic acid, are preferably usable.
  • reaction temperatures can be varied within a certain range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 60 ° C, preferably between 0 ° C and 40 ° C.
  • work is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the oxiranyl-hydroxyethyl-triazoles of the formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.
  • Manner according to usual 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.
  • acid e.g. Hydrogen chloride acid
  • 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 combat unwanted microorganisms, such as fungi and
  • Bacteria can be used in crop protection and material protection.
  • 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 combating Pyricularia oryzae and Pellicularia sasakii on rice and for combating cereal diseases, such as Leptosphaeria nodorum, Cochliobolus sativus, Pyrenophora teres, Pseudocercosporella herpotrichoides, Erysiphe and Fusarium species.
  • cereal diseases such as Leptosphaeria nodorum, Cochliobolus sativus, Pyrenophora teres, Pseudocercosporella herpotrichoides, Erysiphe and Fusarium species.
  • the substances according to the invention have a very good and broad in vitro effect.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired ones
  • 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 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, are also mentioned, which are produced by increasing
  • Microorganisms can be affected.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the ones according to the invention preferably act
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora tenua
  • 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 like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeroginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the substances according to the invention 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 formulations.
  • 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 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, optionally 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 can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally 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 can, for example, 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, for example petroleum fractions
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone
  • liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants such as butane, propane, nitrogen and carbon dioxide; as fixed
  • Carriers are possible: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite,
  • Adhesives such as carboxymethylcellulose, 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 are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance.
  • synergistic effects also occur, which means that the mixture has a higher activity than the sum of the effects of the individual components.
  • Fungicides 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1, 3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoximino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
  • Nickel dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
  • Octhilinone furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofta ⁇ lam, copper sulfate and other copper preparations.
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron, flucythrinate, flufenoxuron, Flufen- prox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxi, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos,
  • Promecarb Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafiuofen, Sulfotep, Sulprof
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenhriazurium, Tralomenhroniazonium Zetamethrin.
  • the active ingredients 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 become. 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.
  • active compound 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%, 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
  • 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 can be determined by test series. In general, the
  • 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 necessary, if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients to increase the spectrum of action or to achieve special effects such as additional protection against insects.
  • These mixtures can have a broader spectrum of activity than the compounds according to the invention. In many cases synergistic effects, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • ⁇ 0.1-1.0 (m, 4H); 2.8-3.5 (m, 2H); 4.1-5.0 (m, 2H); 7.0-7.8 (m, 4H); 8.08 (s); 8.12 (s, together IH); 8.15 (s); 8.19 (s, together IH) ppm.
  • ⁇ 0.1-1.0 (m, 4H); 2.9-3.9 (m, 2H); 4.4-5.2 (m, 2H); 7.2-7.8 (m, 4H); 7.58 (s); 8.0 (s, together IH); 8.5 (s); 8.52 (s, together IH) ppm.
  • 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 Pyrenophora teres.
  • the plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.
  • 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.
  • 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.
  • 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.
  • Leptosphaeria nodorum sprayed The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.
  • the plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of approx. 80%.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • Plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then in a greenhouse at 100% rel. Humidity and 25 ° C.
  • the disease infestation is evaluated 4 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.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • the plants are then placed in a greenhouse at 23 to 24 ° C and at a relative humidity of approx. 75%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while a

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Abstract

L'invention concerne de nouveaux oxyranyle-hydroxyéthyle-triazoles de formule (I), dans laquelle X designe l'hydrogène, un halogène, un alkyle de 1 à 4 atomes de carbone ou un alkoxy de 1 à 4 atomes de carbone, Z désigne un halogène, un alkyle de 1 à 4 atomes de carbone, un halogénoalkyle de 1 à 4 atomes de carbone et de 1 à 5 atomes d'halogène, un alkoxy de 1 à 4 atomes de carbone, un halogénoalkoxy de 1 à 4 atomes de carbone et de 1 à 5 atomes d'halogène, un nitro ou un phényle éventuellement substitué une, deux ou trois fois, de façon identique ou différente, par un halogène, et m vaut 0, 1, 2 ou 3, ainsi que les sels d'addition d'acides et les complexes de sels métalliques de ces composés. L'invention concerne en outre un procédé de fabrication de ces nouveaux produits et leur utilisation comme microbicides pour la protection des végétaux et des matériaux.
PCT/EP1996/001820 1995-05-15 1996-05-02 Oxyranyle-hydroyethyle-atriazoles WO1996036634A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58123/96A AU5812396A (en) 1995-05-15 1996-05-02 Oxiranyl-hydroxyethyl triazoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1995117722 DE19517722A1 (de) 1995-05-15 1995-05-15 Oxiranyl-hydroxyethyl-triazole
DE19517722.3 1995-05-15

Publications (1)

Publication Number Publication Date
WO1996036634A1 true WO1996036634A1 (fr) 1996-11-21

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AU (1) AU5812396A (fr)
DE (1) DE19517722A1 (fr)
WO (1) WO1996036634A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746260A1 (fr) * 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0251086A2 (fr) * 1986-06-23 1988-01-07 The Du Pont Merck Pharmaceutical Company Carbinols fongicides
EP0327913A2 (fr) * 1988-02-09 1989-08-16 Bayer Ag Azolylméthyloxiranes substitués
EP0345639A1 (fr) * 1988-06-04 1989-12-13 BASF Aktiengesellschaft Alpha-hydroxy azolyléthyloxirannes et fongicides les contenant
EP0565463A1 (fr) * 1992-04-08 1993-10-13 Rhone-Poulenc Agrochimie Dérivés triazole et imidazole fongicides
DE4419812A1 (de) * 1993-09-16 1995-03-23 Bayer Ag Hydroxyethyl-azolyl-Derivate

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0251086A2 (fr) * 1986-06-23 1988-01-07 The Du Pont Merck Pharmaceutical Company Carbinols fongicides
EP0327913A2 (fr) * 1988-02-09 1989-08-16 Bayer Ag Azolylméthyloxiranes substitués
EP0345639A1 (fr) * 1988-06-04 1989-12-13 BASF Aktiengesellschaft Alpha-hydroxy azolyléthyloxirannes et fongicides les contenant
EP0565463A1 (fr) * 1992-04-08 1993-10-13 Rhone-Poulenc Agrochimie Dérivés triazole et imidazole fongicides
DE4419812A1 (de) * 1993-09-16 1995-03-23 Bayer Ag Hydroxyethyl-azolyl-Derivate

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746260A1 (fr) * 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués

Also Published As

Publication number Publication date
AU5812396A (en) 1996-11-29
DE19517722A1 (de) 1996-11-21

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