EP0000018A1 - Complexes métalliques de dérivés du 1-phényl-2-triazolyl-éthane, leur préparation ainsi que leur utilisation comme fongicides - Google Patents

Complexes métalliques de dérivés du 1-phényl-2-triazolyl-éthane, leur préparation ainsi que leur utilisation comme fongicides Download PDF

Info

Publication number
EP0000018A1
EP0000018A1 EP78100030A EP78100030A EP0000018A1 EP 0000018 A1 EP0000018 A1 EP 0000018A1 EP 78100030 A EP78100030 A EP 78100030A EP 78100030 A EP78100030 A EP 78100030A EP 0000018 A1 EP0000018 A1 EP 0000018A1
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
phenyl
triazolyl
stands
integers
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.)
Granted
Application number
EP78100030A
Other languages
German (de)
English (en)
Other versions
EP0000018B1 (fr
Inventor
Wolfgang Dr. Krämer
Helmut Dr. Timmler
Karl Heinz Dr. Büchel
Wilhelm Dr. Brandes
Paul-Ernst Dr. Frohberger
Hans Dr. Scheinpflug
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0000018A1 publication Critical patent/EP0000018A1/fr
Application granted granted Critical
Publication of EP0000018B1 publication Critical patent/EP0000018B1/fr
Expired legal-status Critical Current

Links

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
    • 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
    • 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 metal salt complexes of 1-phenyl-2-triazolyl-ethyl derivatives, a process for their preparation and their use as fungicides.
  • the metal complexes of 1-phenyl-2-triazolyl-ethyl derivatives according to the invention show a considerably higher fungicidal activity, in particular against rust and mildew types, than the 1- [ß-aryl-ß (R-oxy ) ethyl] imidazoles and triazoles, for example 1- [ß-butoxy-ß- (4'-chlorophenyl) ethyl] imidazole, which are chemically and functionally obvious substances, and as the zinc-ethylene-1,2-bis-dithiocarbamidate, which is a known substance with the same direction of action.
  • the active compounds according to the invention thus represent an enrichment of the technology.
  • Formula (II) provides a general definition of the 1-phenyl-2-triazolyl-ethyl derivatives to be used as starting materials.
  • R preferably represents halogen, in particular fluorine, chlorine and bromine; for nitro and cyano; further preferably for alkyl and alkylsulfonyl with 1 to 4 carbon atoms, for alkoxy and alkylthio with 1 to 2 carbon atoms and for haloalkyl with up to 4 carbon atoms and up to 5 halogen atoms, in particular with up to 2 carbon atoms and up to 3 identical or different halogen atoms, fluorine and chlorine preferably being considered as halogen atoms and trifluoromethyl specifically being mentioned as an example of halogenoalkyl.
  • R also preferably represents phenyl or phenoxy which may be mono- or polysubstituted in the same way or differently, the preferred substituents being: halogen, in particular fluorine, chlorine and bromine; Cyano, nitro, and haloalkyl with up to 2 carbon atoms and up to 3 identical or different halogen atoms, fluorine and chlorine preferably being considered as halogen atoms, and trifluoromethyl may be mentioned specifically as an example of haloalkyl.
  • the index n preferably stands for integers from 0 to 3.
  • R 1 preferably has the meaning given in the definition of the invention.
  • R 2 preferably represents alkyl, alkenyl and alkynyl each having up to 4 carbon atoms, cycloalkyl, and preferably aryl, arylalkyl or arylalkenyl optionally substituted in the aryl part having 6 to 10 carbon atoms in the aryl part and up to 4 carbon atoms in the alkyl or alkenyl part, such as, for example, phenyl, naphthyl, benzyl, naphthylmethyl and styryl, the preferred substituents being: halogen; especially fluorine, chlorine, bromine; Cyano, nitro, amino, alkyl having 1 to 4 carbon atoms, haloalkyl having up to 2 carbon atoms and up to 3 identical or different halogen atoms, the halogen being in particular fluorine and chlorine, for example trifluoromethyl, and optionally halogen, in particular fluorine or Chlorine, substituted phenoxy.
  • R 3 preferably stands for the radicals which have already been mentioned as preferred for R 2 and for hydrogen.
  • Dar index n preferably has the meaning given in the definition of the invention.
  • R 4 preferably represents the radicals which are already mentioned as preferred for R 2 , and also haloalkyl having 1 to 2 carbon and 1 to 5 halogen atoms, fluorine and chlorine being mentioned in particular, such as trifluoromethyl, dichloromethyl and chloromethyl, as well as for given if in the phenyl part substituted phenoxyalkyl having 1 or 2 carbon atoms in the alkyl part, the preferred substituents being: halogen, in particular fluorine or chlorine, amino, cyano, nitro or alkyl having 1 to 2 carbon atoms.
  • R 4 preferably represents amino, alkylamino, dialkylamino and alkylalkylcarbonylamino, each having 1 to 4, in particular 1 to 2, carbon atoms in each alkyl part and also phenylamino which is optionally substituted by halogen, in particular fluorine or chlorine, nitro and cyano.
  • the procedure is expediently started from a 1-hydroxy-1-phenyl-2-triazolylethane derivative, the latter in a suitable inert solvent using alkali metal hydride or alkali metal amide in the alkali metal alcoholate of the formula ( IV) transferred. and the latter is reacted immediately without isolation with a halide of the formula (V), the compounds of the formula (II) being obtained in one operation with the emergence of alkali halide.
  • the preparation of the alkanolates of the formula (IV) and the reaction with the halide of the formula (V) are advantageously carried out in a two-phase system, such as, for example, aqueous sodium or potassium hydroxide solution / toluene or methylene chloride, with the addition of a phase transfer -Catalyst, such as ammonium or phosphonium compounds, performed.
  • a phase transfer -Catalyst such as ammonium or phosphonium compounds
  • the 1-halogen-1-phenyl-2-triazolyl-ethane derivatives of the formula (VI) are also known (compare DT-OS 25 47 954 [Le A 16 750]).
  • Formula (III) provides a general definition of the metal salts which are also required for the preparation of the metal complexes according to the invention.
  • Me preferably stands for metals of the II. To IV. Main groups and of I. and II. As well as IV. To VIII. Subgroups, copper, zinc, manganese, magnesium, tin, iron and nickel being particularly mentioned.
  • A preferably represents chloride, bromide, iodide, nitrate, sulfate and phosphate anions.
  • the index p preferably stands for integers from 1 to 4 and k preferably stands for any numbers from 0 to 8.
  • the required metal salts of the formula (III) are generally known, easily accessible compounds.
  • Water and all inert organic solvents are suitable as diluents for the implementation according to the invention. These preferably include alcohols such as methanol and ethanol, ketones such as acetone or ethyl methyl ketone, and ethers such as e.g. Diethyl ether and dioxane.
  • reaction temperatures can be varied within a wide range. Generally one works between 0 and 40 ° C, preferably between 15 and 30 ° C.
  • the stoichiometric amount (depending on the oxidation state of the metal) of the compound of the formula (II) is employed per mol of the metal salt (III). These ratios can be exceeded by up to 20 mol% without significant reduction in yield.
  • Working up takes place in a manner which is customary and generally known for organic compounds, e.g. by suctioning off the precipitated complex and cleaning by recrystallization, e.g. from alcohol.
  • the active substances according to the invention have a strong fungitoxic effect. They do not damage crops in the concentrations necessary to control fungi. For these reasons, they are suitable for use as crop protection agents for combating fungi. Fungitoxic agents in plant protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, 'Deuteromycetes.
  • the active compounds according to the invention have a broad spectrum of activity and can be used against parasitic fungi which attack above-ground parts of plants or attack the plants from the ground, and against seed-borne pathogens. They are particularly effective against parasitic fungi on above-ground parts of plants.
  • the active substances according to the invention can be used with particularly good results for combating Venturia species, such as against the pathogen causing apple scab (Fusicladium dendriticum), powdery mildew fungi, for example for combating powdery mildew (Podosphaera leucotricha) and powdery mildew, and against other cereal diseases.
  • Venturia species such as against the pathogen causing apple scab (Fusicladium dendriticum), powdery mildew fungi, for example for combating powdery mildew (Podosphaera leucotricha) and powdery mildew, and against other cereal diseases.
  • apple scab Food scab
  • powdery mildew fungi for example for combating powdery mildew (Podosphaera leucotricha) and powdery mildew
  • the partially systemic effect of the substances This is how plants can be protected against fungal attack if the active ingredient is supplied to the aerial parts of the plant via the soil and the roots.
  • the active compounds according to the invention can be used as crop protection agents for treating seeds or soil and for treating above-ground parts of plants.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are manufactured in a known manner, e.g. B. 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.
  • 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 can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, benzene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B.
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and pressure, e.g. B.
  • aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; as an emulsifier; nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
  • active compounds such as fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
  • the formulations generally contain between 0.1 and. 95 percent by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting, scattering, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 0.1 and 0.00001 percent by weight. Preferably between 0.05 and 0.0001%.
  • active compound 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • Fusicladium test (apple) / protective - The amount of active ingredient required for the desired active ingredient concentration in the spray liquid is mixed with the stated amount of solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.
  • the spray liquid is used to spray young apple seedlings that are in the 4- to 6-leaf stage until they drip wet.
  • the plants remain in the greenhouse for 24 hours at 20 ° C. and a relative humidity of 70%. They are then inoculated with an aqueous conidia suspension of the apple scab pathogen (Fusicladium dendriticum) and incubated for 18 hours in a humid chamber at 18 to 20 ° C and 100% relative humidity.
  • the infestation of the seedlings is determined 15 days after the inoculation.
  • the rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.
  • the spray liquid is used to spray young apple seedlings that are in the 4- to 6-leaf stage until they drip wet.
  • the plants remain in the greenhouse for 24 hours at 20 ° C. and a relative humidity of 70%. They are then inoculated by dusting with conidia of the powdery mildew pathogen (Podosphaera leucotricha) and placed in a greenhouse at a temperature of 21 to 23 ° C and a relative humidity of approx. 70%.
  • the infestation of the seedlings is determined 10 days after the inoculation.
  • the rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.
  • active compound 0.25 part by weight of active compound is taken up in 25 parts by weight of dimethylformamide and 0.06 part by weight of alkylaryl polyglycol ether, and 975 parts by weight of water are added. The concentrate is diluted with water to the desired final concentration of the spray mixture.
  • the single-leafed barley young plants of the Amsel variety are sprayed with the preparation of active compound as dewy. After drying, the barley plants are dusted with spores from Erysiphe graminis var.hordei.
  • the stocking of the plants with mildew pustules is evaluated.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The lower the mildew infestation, the more effective the active ingredient. Active substances, active substance concentrations in the spray mixture and degrees of infestation are shown in the table below.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. So 0% means no infection and 100% the same degree of infection as with the untreated control. The lower the mildew infestation, the more effective the active ingredient.
  • Active substances, active substance concentrations in the seed treatment agent as well as its application rate and the percentage of mildew infestation come from the following table.
  • the amount of active ingredient required for the desired active ingredient concentration in the nutrient medium is mixed with the stated amount of the solvent mixture.
  • the concentrate is thoroughly mixed with the liquid nutrient medium cooled to 42 ° C in the stated ratio and poured into Petri dishes with a diameter of 9 cm. Control plates are also set up without admixture.
  • the plates are inoculated with the fungus species listed in the table and incubated at about 21 ° C.

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)
EP78100030A 1977-06-03 1978-06-01 Complexes métalliques de dérivés du 1-phényl-2-triazolyl-éthane, leur préparation ainsi que leur utilisation comme fongicides Expired EP0000018B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772725214 DE2725214A1 (de) 1977-06-03 1977-06-03 Metallsalzkomplexe von 1-phenyl-2- triazolyl-aethyl-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE2725214 1977-06-03

Publications (2)

Publication Number Publication Date
EP0000018A1 true EP0000018A1 (fr) 1978-12-20
EP0000018B1 EP0000018B1 (fr) 1981-01-07

Family

ID=6010698

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100030A Expired EP0000018B1 (fr) 1977-06-03 1978-06-01 Complexes métalliques de dérivés du 1-phényl-2-triazolyl-éthane, leur préparation ainsi que leur utilisation comme fongicides

Country Status (23)

Country Link
US (1) US4366152A (fr)
EP (1) EP0000018B1 (fr)
JP (1) JPS543069A (fr)
AR (1) AR226278A1 (fr)
AT (1) AT357374B (fr)
AU (1) AU516653B2 (fr)
BR (1) BR7803550A (fr)
CA (1) CA1106386A (fr)
CS (1) CS199530B2 (fr)
DD (1) DD137659A5 (fr)
DE (2) DE2725214A1 (fr)
DK (1) DK248778A (fr)
EG (1) EG13358A (fr)
ES (1) ES470459A1 (fr)
HU (1) HU179670B (fr)
IL (1) IL54841A0 (fr)
IT (1) IT1098307B (fr)
NZ (1) NZ187449A (fr)
PL (1) PL109268B1 (fr)
PT (1) PT68099A (fr)
SU (1) SU1001848A3 (fr)
TR (1) TR19767A (fr)
ZA (1) ZA783177B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061789B1 (fr) * 1981-03-27 1985-10-23 Janssen Pharmaceutica N.V. Dérivés du triazole à activité antimicrobienne
EP0275955A1 (fr) * 1987-01-21 1988-07-27 Ciba-Geigy Ag Composition microbicide

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2833194A1 (de) * 1978-07-28 1980-02-14 Basf Ag Triazolderivate
US5266585A (en) * 1981-05-12 1993-11-30 Ciba-Geigy Corporation Arylphenyl ether derivatives, compositions containing these compounds and use thereof
GB2104065B (en) * 1981-06-04 1985-11-06 Ciba Geigy Ag Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms
DE3208194A1 (de) * 1982-03-06 1983-09-08 Bayer Ag, 5090 Leverkusen Substituierte azolylethyl-oximinoalkyl-ether, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US4533659A (en) * 1982-06-09 1985-08-06 Ciba-Geigy Corporation Microbicidal 2-(1H-1,2,4-triazolylmethyl-1'-yl)-2-siloxy-2-phenyl-acetates
US4517194A (en) * 1982-06-25 1985-05-14 Ciba-Geigy Corporation Azolylmandelic acid derivatives and use thereof for controlling microorganisms
US4584008A (en) * 1982-07-14 1986-04-22 Chevron Research Company Aldol adducts containing triazole groups
EP0126430B1 (fr) * 1983-05-19 1991-08-28 Ciba-Geigy Ag Procédé pour la préparation de dérivés de 1-triazolyléthyléthers, composés microbicides contenant des dérivés nouveaux de 1-triazolyl-phenoxyphényléthyléther comme ingrédients actifs et leur application
US4870094A (en) * 1984-05-02 1989-09-26 Uniroyal Chemical Company, Inc. Substituted imidazoles and triazoles
US5039332A (en) * 1985-09-19 1991-08-13 Uniroyal Chemical Company, Inc. Substituted oxathiolanes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2423987C2 (de) * 1974-05-17 1986-01-16 Bayer Ag, 5090 Leverkusen Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE2502932C2 (de) * 1975-01-24 1985-04-18 Bayer Ag, 5090 Leverkusen Metallkomplexe von N-Trityl-azolen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE2547953A1 (de) * 1975-10-27 1977-04-28 Bayer Ag (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Keine Entgegenhaltungen *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061789B1 (fr) * 1981-03-27 1985-10-23 Janssen Pharmaceutica N.V. Dérivés du triazole à activité antimicrobienne
EP0275955A1 (fr) * 1987-01-21 1988-07-27 Ciba-Geigy Ag Composition microbicide
US4992458A (en) * 1987-01-21 1991-02-12 Ciba-Geigy Corporation 1-phenoxyphenyl-1-triazolylmethyl-carbinol compound as microbicides

Also Published As

Publication number Publication date
US4366152A (en) 1982-12-28
EP0000018B1 (fr) 1981-01-07
PT68099A (en) 1978-06-01
HU179670B (en) 1982-11-29
PL207335A1 (pl) 1979-02-26
BR7803550A (pt) 1979-02-20
ATA401778A (de) 1979-11-15
IT1098307B (it) 1985-09-07
EG13358A (en) 1982-03-31
ZA783177B (en) 1979-06-27
CA1106386A (fr) 1981-08-04
ES470459A1 (es) 1979-01-01
JPS6337788B2 (fr) 1988-07-27
TR19767A (tr) 1979-11-30
AU516653B2 (en) 1981-06-18
PL109268B1 (en) 1980-05-31
SU1001848A3 (ru) 1983-02-28
DE2860395D1 (en) 1981-02-26
DK248778A (da) 1978-12-04
NZ187449A (en) 1979-11-01
IT7824172A0 (it) 1978-06-02
DE2725214A1 (de) 1978-12-14
CS199530B2 (en) 1980-07-31
IL54841A0 (en) 1978-08-31
DD137659A5 (de) 1979-09-19
AU3685078A (en) 1979-12-13
JPS543069A (en) 1979-01-11
AT357374B (de) 1980-07-10
AR226278A1 (es) 1982-06-30

Similar Documents

Publication Publication Date Title
EP0000017B1 (fr) Sels de 1-(2-phényléthyl)-triazolium, leur préparation et leur utilisation comme fongicides
EP0004917B1 (fr) Oximino-triazolyl-éthanes, procédé pour leur préparation ainsi que leur utilisation comme fongicides
DE2635663C2 (fr)
CH625793A5 (fr)
EP0019189B1 (fr) Agents fongicides, procédé pour leur préparation, ainsi que leur utilisation comme fongicides
EP0000018B1 (fr) Complexes métalliques de dérivés du 1-phényl-2-triazolyl-éthane, leur préparation ainsi que leur utilisation comme fongicides
DE2720949A1 (de) Azolylaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0019131B1 (fr) Dérivés fluorés du 1-triazolyl butane, procédé pour leur préparation et leur application comme fongicides
EP0054865A1 (fr) 1-Azolyl-butan-2-ones substitués, procédé de leur préparation et leur application comme fongicides ainsi que comme intermédiaires
EP0103798B1 (fr) Azolylalkyl-t-butyl-cétones et -carbinols substitués
EP0104549B1 (fr) Azolylbutanoles
EP0121888B1 (fr) Dérivés 1-azolyl-3-pyrazolyl-2-propanols, leur procédé de préparation et leur application comme fongicides
EP0131845A2 (fr) Utilisation de diazolylalkylecarbinols substitués pour la protection de plantes contre les champignons
EP0076370B1 (fr) Dérivés phénoxy azolyl substitués, leur procédé de synthèse et leur application comme fongicides
EP0029542A2 (fr) Dérivés de l'hydroxybutyl-imidazole, procédé pour leur préparation, intermédiaires pour celle-ci et leur utilisation comme fongicides
DE2702102A1 (de) N-azolylacetyl-n-phenyl-alaninester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0002678A2 (fr) Ethers azolylalkyl-pyridinyl, leur procédé de préparation ainsi que leur utilisation comme fongicides
DE2632603A1 (de) Halogenierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0042980A2 (fr) 1-Azolyl-1-phénoxy-3,3-diméthyl-butan-2-ones et -2-ols, substitués en position 4, leur procédé de préparation et leur application comme fongicides
EP0057864B1 (fr) Dérivés de 2-azolylméthyl-1,3-dioxolanne et - dioxanne, procédé pour leur préparation et leur application comme fongicide
DE2928967A1 (de) Azolyl-alkenole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0019190B1 (fr) Utilisation des hydroxyalkyl-imidazoles comme fongicides
EP0073331B1 (fr) 5-Aryloxy-5-azolyl-3,3-diméthyl-1-pentène-4-ones et -ols, leur procédé de synthèse et leur application comme fongicides
CH616664A5 (fr)
EP0024538B1 (fr) 1,2,4-Triazolyl-énol éthers, procédé pour leur préparation et leur utilisation comme fongicides

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE FR GB NL SE

17P Request for examination filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE CH DE FR GB NL SE

REF Corresponds to:

Ref document number: 2860395

Country of ref document: DE

Date of ref document: 19810226

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19840630

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19850602

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19900517

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19900522

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19900620

Year of fee payment: 13

Ref country code: CH

Payment date: 19900620

Year of fee payment: 13

Ref country code: BE

Payment date: 19900620

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19900630

Year of fee payment: 13

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19910601

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19910630

Ref country code: BE

Effective date: 19910630

BERE Be: lapsed

Owner name: BAYER A.G.

Effective date: 19910630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19920101

GBPC Gb: european patent ceased through non-payment of renewal fee
NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19920228

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19920401

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

EUG Se: european patent has lapsed

Ref document number: 78100030.2

Effective date: 19860728

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT