EP0000017B1 - 1-(2-Phenyläthyl)-triazolium-Salze, Verfahren zur ihrer Herstellung sowie ihre Verwendung als Fungizide - Google Patents

1-(2-Phenyläthyl)-triazolium-Salze, Verfahren zur ihrer Herstellung sowie ihre Verwendung als Fungizide Download PDF

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Publication number
EP0000017B1
EP0000017B1 EP78100029A EP78100029A EP0000017B1 EP 0000017 B1 EP0000017 B1 EP 0000017B1 EP 78100029 A EP78100029 A EP 78100029A EP 78100029 A EP78100029 A EP 78100029A EP 0000017 B1 EP0000017 B1 EP 0000017B1
Authority
EP
European Patent Office
Prior art keywords
halogen
general formula
phenylethyl
triazolium
carbon atoms
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.)
Expired
Application number
EP78100029A
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German (de)
English (en)
French (fr)
Other versions
EP0000017A1 (de
Inventor
Helmut Dr. Timmler
Wolfgang Dr. Krämer
Karl Heinz Prof.Dr. Büchel
Wilhelm Dr. Brandes
Paul-Ernst Dr. Frohberger
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 EP0000017A1 publication Critical patent/EP0000017A1/de
Application granted granted Critical
Publication of EP0000017B1 publication Critical patent/EP0000017B1/de
Expired legal-status Critical Current

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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
    • 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 invention relates to 1- (2-phenylethyl) triazolium salts, a process for their preparation and their use as fungicides.
  • the 1- (2-phenylethyl) triazolium salts 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) known from the prior art.
  • 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.
  • the alkyl part preferably occurs at the nitrogen atom 4 of the 1,2,4-triazol-1-yl radical, as can be seen from the nuclear magnetic resonance data; depending on the reactivity of the alkyl halide and the starting product of the general formula II, however, alkylation on nitrogen atom 1 of the 1,2,4-triazol-1-yl radical can also be carried out. Both types of compounds and the mixtures obtained in this alkylation are claimed according to the invention.
  • the 1-phenyl-2-triazolylethyl derivatives to be used as starting materials are generally defined by the general formula 11.
  • the starting materials of the general formula II are known (cf. DE-OS 25 47 953, DE-OS 26 40 823, DE-OS 26 28 419 and DE-OS 26 45 496). They can be obtained by the processes described there, e.g.
  • the procedure is advantageously carried out in such a way that a 1-hydroxy-1-phenyl-2-triazolylethane derivative is used, the latter being converted into the alkali metal alcoholate of the general formula IV in a suitable inert solvent by means of alkali metal hydride or alkali metal amide , and the latter is reacted immediately without isolation with a halide of the general formula V, the compounds of the general formula II being obtained in one operation with the emergence of alkali halide.
  • the preparation of the alkanolates of the general formula IV and the reaction with the halide of the general formula V are advantageously carried out in a two-phase system, such as, for example, aqueous sodium hydroxide solution or potassium hydroxide solution / toluene or methylene chloride, with the addition of a phase transfer catalyst, such as ammonium or phosphonium compounds.
  • a phase transfer catalyst such as ammonium or phosphonium compounds.
  • the 1-halogen-1-phenyl-2-triazolyl-ethane derivatives of the general formula VI are also known (cf. DE-OS 25 47 954).
  • halides also to be used as starting materials are generally defined by the general formula III.
  • the starting materials of the general formula III are generally known compounds of organic chemistry, or they can be obtained in a generally known and customary manner.
  • Polar organic solvents are preferably used as diluents for the reaction according to the invention. These preferably include nitriles, such as acetonitrile; Sulfoxides such as dimethyl sulfoxide; Formamides such as dimethylformamide; Ketones such as acetone; Ethers such as diethyl ether and tetrahydrofuran and chlorinated hydrocarbons such as methylene chloride and chloroform.
  • nitriles such as acetonitrile
  • Sulfoxides such as dimethyl sulfoxide
  • Formamides such as dimethylformamide
  • Ketones such as acetone
  • Ethers such as diethyl ether and tetrahydrofuran and chlorinated hydrocarbons such as methylene chloride and chloroform.
  • reaction temperatures can be varied within a wide range in the process according to the invention. In general, between about 0 to 120 ° C, preferably at 20 to 90 ° C, or at the boiling point of the solvent.
  • the process according to the invention is preferably carried out in molar amounts.
  • the compounds of the general formula I are isolated in a customary manner.
  • halogen ion exchange which may be carried out in accordance with the process according to the invention, is carried out in a generally known manner (cf. DE-OS 2 504 114) by using the 1- (2-phenylethyl) triazolium halides of the general formula converted into the corresponding triazolium hydroxides by means of a base or an anion exchange resin and then reacted with an appropriate acid.
  • 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. Fun gitoxic agents in crop 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 compounds according to the invention can be used with particularly good success for combating Venturia species, such as against the pathogen causing apple scab (Fusicladium dendriticum), for powdery mildew fungi, for example for combating powdery mildew (Podosphaera leucotricha) and powdery mildew, and for 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 for other cereal diseases.
  • 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 made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • 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.
  • Petroleum fractions 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 excipients are those liquids which are gaseous at normal temperature and pressure, e.g.
  • 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 compound, 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.
  • active ingredient For soil treatment, amounts of active ingredient from 1 to 100 g per soil, in particular 10 to 200 g, are required.
  • 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, which 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%. Then they are inoculated by dusting with conidia of the powdery mildew pathogen (Podosphaera leucotricha) and placed in a greenhouse with a temperature of 21 to 23 ° C and a relative humidity of approx. 70%.
  • the powdery mildew pathogen Podosphaera leucotricha
  • the infestation of the seedlings is determined 10 days after the inoculation.
  • the rating values received are converted into percent infestation. 0% means no attack, 100% means that the plants are completely infected.
  • 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, which 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.
  • 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 substances, active substance concentrations in the spray mixture and degrees of infestation are shown in the table below.
  • the active ingredients are used as powdered seed treatment agents. They are produced by stripping the respective active ingredient with a mixture of equal parts by weight of talc and kieselguhr to a fine powdery mixture with the desired active ingredient concentration.
  • 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 seed treatment agent as well as its application rate and the percentage of mildew infestation are shown in the table below.
  • the amount of active ingredient required for the desired active ingredient concentration in the culture 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.
  • the evaluation takes place after 4-10 days depending on the growth rate of the mushrooms.
  • the radial mycelial growth on the treated culture media is compared with the growth on the control culture media. Mushroom growth is rated using the following indicators:

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
EP78100029A 1977-06-04 1978-06-01 1-(2-Phenyläthyl)-triazolium-Salze, Verfahren zur ihrer Herstellung sowie ihre Verwendung als Fungizide Expired EP0000017B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2725314 1977-06-04
DE19772725314 DE2725314A1 (de) 1977-06-04 1977-06-04 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

Publications (2)

Publication Number Publication Date
EP0000017A1 EP0000017A1 (de) 1978-12-20
EP0000017B1 true EP0000017B1 (de) 1981-09-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100029A Expired EP0000017B1 (de) 1977-06-04 1978-06-01 1-(2-Phenyläthyl)-triazolium-Salze, Verfahren zur ihrer Herstellung sowie ihre Verwendung als Fungizide

Country Status (16)

Country Link
EP (1) EP0000017B1 (cs)
JP (1) JPS543070A (cs)
AU (1) AU3684878A (cs)
BR (1) BR7803551A (cs)
CA (1) CA1100976A (cs)
CS (1) CS199531B2 (cs)
DD (1) DD137658A5 (cs)
DE (2) DE2725314A1 (cs)
DK (1) DK248378A (cs)
ES (1) ES470458A1 (cs)
IL (1) IL54840A (cs)
IT (1) IT7824171A0 (cs)
PL (1) PL109267B1 (cs)
PT (1) PT68100A (cs)
TR (1) TR19791A (cs)
ZA (1) ZA783176B (cs)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10519122B2 (en) 2013-01-09 2019-12-31 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
US10905122B2 (en) 2016-03-16 2021-02-02 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
US10918107B2 (en) 2015-05-20 2021-02-16 Conopco, Inc. Encapsulated lactams
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6224254Y2 (cs) * 1979-09-17 1987-06-20
DE2937595A1 (de) * 1979-09-18 1981-04-02 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von 1-azolyl-1-phenoxy-alkan-2-onen
CA1179678A (en) * 1981-03-27 1984-12-18 Elmar Sturm Antimicrobial triazole derivatives
GB2143815B (en) * 1983-05-19 1988-01-20 Ciba Geigy Ag Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives
DE3319845A1 (de) * 1983-06-01 1984-12-06 Basf Ag, 6700 Ludwigshafen Arylalkylimidazolium- und -triazoliumsalze, verfahren zu ihrer herstellung und ihre verwendung als mikrozide
IT1200422B (it) * 1985-03-19 1989-01-18 Ripari Gero Ist Farm Biolog Composto con attivita' antimicrobia,sua preparazione e composizioni farmaceutiche che lo contengono
ES2016660B3 (es) * 1987-01-21 1990-11-16 Ciba-Geigy Ag Agente microbicida.
BR9307206A (pt) * 1992-10-09 1999-03-30 Uniroyal Chemical Ltd Composto processo de preparação composição fungicida método para controlar fungos fitopalogênicos
MX356322B (es) 2011-07-13 2018-05-23 Basf Se Compuestos sustituidos fungicidas de 2-[2-halogenalquil-4-(fenoxi) -fenil]-1-[1,2,4]triaxol-1-il-etanol.
JP2014520828A (ja) 2011-07-15 2014-08-25 ビーエーエスエフ ソシエタス・ヨーロピア 殺菌性アルキル−置換２−［２−クロロ−４−（４−クロロ−フェノキシ）−フェニル］−１−［１，２，４］トリアゾール−１−イル−エタノール化合物
BR112014000538A2 (pt) 2011-07-15 2016-08-23 Basf Se compostos, processo para a preparação dos compostos, composições agroquímicas, utilização dos compostos e semente revestida
JP2014529594A (ja) 2011-08-15 2014-11-13 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 殺菌性置換１−｛２−シクリルオキシ−２−［２−ハロ−４−（４−ハロゲン−フェノキシ）−フェニル］−エチル｝−１ｈ−［１，２，４］トリアゾール化合物
AR087535A1 (es) 2011-08-15 2014-04-03 Basf Se Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]-2-etoxi-etil}-1h-[1,2,4]triazol sustituidos
MX2014000824A (es) 2011-08-15 2014-02-27 Basf Se Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]- 2-alcoxi-3-metil-butil}-1h-[1,2,4]triazol sustituidos.
WO2013024083A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-ethyl}-1h-[1,2,4]triazole compounds
US10759767B2 (en) 2012-12-20 2020-09-01 BASF Agro B.V. Compositions comprising a triazole compound
UA118265C2 (uk) 2013-07-08 2018-12-26 Басф Агро Б.В. Композиції, що містять триазольну сполуку і біопестицид
EP3160229A1 (en) 2014-06-25 2017-05-03 BASF Agro B.V. Pesticidal compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ181916A (en) * 1975-09-10 1979-01-11 Ici Ltd 1-substituted-1,2,4-triazoles and fungicidal compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10519122B2 (en) 2013-01-09 2019-12-31 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
US10918107B2 (en) 2015-05-20 2021-02-16 Conopco, Inc. Encapsulated lactams
US10905122B2 (en) 2016-03-16 2021-02-02 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits

Also Published As

Publication number Publication date
IL54840A0 (en) 1978-08-31
JPS543070A (en) 1979-01-11
CS199531B2 (en) 1980-07-31
AU3684878A (en) 1979-12-13
PL109267B1 (en) 1980-05-31
IL54840A (en) 1982-03-31
DD137658A5 (de) 1979-09-19
PT68100A (de) 1978-06-01
DE2725314A1 (de) 1978-12-14
EP0000017A1 (de) 1978-12-20
IT7824171A0 (it) 1978-06-02
TR19791A (tr) 1979-12-19
PL207336A1 (pl) 1979-02-26
ZA783176B (en) 1979-06-27
DE2861233D1 (en) 1981-12-10
CA1100976A (en) 1981-05-12
BR7803551A (pt) 1979-02-20
ES470458A1 (es) 1979-01-01
DK248378A (da) 1978-12-05

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