EP0000940B1 - Gamma-Azolylalkohole, und ihre Verwendung zur Regulierung des Pflanzenwachstums - Google Patents

Gamma-Azolylalkohole, und ihre Verwendung zur Regulierung des Pflanzenwachstums Download PDF

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Publication number
EP0000940B1
EP0000940B1 EP78100725A EP78100725A EP0000940B1 EP 0000940 B1 EP0000940 B1 EP 0000940B1 EP 78100725 A EP78100725 A EP 78100725A EP 78100725 A EP78100725 A EP 78100725A EP 0000940 B1 EP0000940 B1 EP 0000940B1
Authority
EP
European Patent Office
Prior art keywords
triazolyl
dimethylpentan
weight
parts
azolyl
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
EP78100725A
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German (de)
English (en)
French (fr)
Other versions
EP0000940A2 (de
EP0000940A3 (en
Inventor
Costin Dr. Rentzea
Johann Dr. Jung
Hubert Dr. Sauter
Gerd Dr. Heilen
Bernd Dr. Zeeh
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0000940A2 publication Critical patent/EP0000940A2/de
Publication of EP0000940A3 publication Critical patent/EP0000940A3/xx
Application granted granted Critical
Publication of EP0000940B1 publication Critical patent/EP0000940B1/de
Expired legal-status Critical Current

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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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • 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
    • 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
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-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

Definitions

  • the present invention relates to new valuable y-azolyl alcohols with good biological activity, agents for regulating plant growth which contain these compounds and methods for regulating plant growth with these compounds.
  • Plant growth regulators can e.g. cause a reduction in length growth, induce germination or flowering, increase frost resistance, or promote or inhibit the formation of side shoots.
  • y-azolyl alcohols have the general formula in which R 1 and R 2 are the same or different and are alkyl with up to 5 carbon atoms, cycloalkyl, furanyl, thiophenyl, pyridyl, naphthyl or phenyl, the phenyl radical being halogen, alkyl, alkoxy, alkenyloxy, hydroxy, nitro, Trifluoromethyl can be substituted and R 1 can also be biphenyl and Az means an imidazolyl, pyrazolyl, 1,2,4-triazolyl or a 1,2,3-triazole radical, show a very good plant growth-regulating activity.
  • the y-azolyl alcohols according to the invention are very suitable for regulating growth in numerous plants, which is manifested in particular in a reduction in length growth. The effect is better than with known growth regulators.
  • the effect is particularly evident in cereals, e.g. Wheat, rye, barley, rice and oats, but also for dicots (e.g. sunflowers, tomatoes, vines, cotton, rapeseed) and various ornamental plants, such as poinsettias and hibiscus.
  • dicots e.g. sunflowers, tomatoes, vines, cotton, rapeseed
  • various ornamental plants such as poinsettias and hibiscus.
  • the treated plants accordingly have a lower growth; a darker leaf color can also be observed.
  • the y-azolyl alcohols according to the invention can be obtained from the crop plants both via the soil, i.e. through the root, as well as by spraying over the leaf. Due to the high plant tolerance, the application rate can be varied widely; in general, however, applications of 0.25 to 12 kg / ha should be considered sufficient.
  • R 1 means, for example, methyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, furfuryl, thiophenyl, naphthyl, biphenylyl, phenyl, p-tolyl, m- and p-methoxy-phenyl, p -Fluorophenyl, p-chlorophenyl or 2,4-dichlorophenyl.
  • R 2 means, for example, tert-butyl, furfuryl, 2-methyl-furfuryl, thiophenyl, pyridyl, naphthyl, phenyl, p-tolyl, p-isopropyl-phenyl, o- and p-methoxy-phenyl, 2,3-dimethoxy- phenyl, o-hydroxyphenyl, p-chlorophenyl, m- and p-bromophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl or p-nitrophenyl.
  • the starting materials of formula (II) can be prepared as follows.
  • ⁇ - (1,2,4-triazol- (1)) - yl, ⁇ -imidazolyl and ⁇ -pyrazolyl ketones of the formula (II) are obtained if appropriately substituted ⁇ , ⁇ -unsaturated ketones are used with the desired azoles in the presence of solvent or diluent at temperatures between 20 and 80 ° C or if instead of ⁇ , ⁇ -unsaturated ketones the corresponding aldehydes and ketones in the presence of azoles and optionally in the presence of a basic catalyst and optionally in the presence of a Converts diluent. Regulation A
  • a solution of 11 g (0.11 mol) of 3,3-dimethylbutan-2-one and 14 g (0.1 mol) of p-chlorobenzaldehyde in 120 ml of ethanol are mixed with 10 ml of 20% aqueous sodium hydroxide solution and 2 hours at 50 ° C stirred. After adding 13.8 g (0.2 mol) of 1,2,4-triazole, the mixture is stirred at 50 ° C. for a further 8 hours. The solvent is then distilled off and the remaining residue is partitioned between 300 ml of water and 300 ml of ether.
  • the ethereal solution is dried over CaS0 4 , filtered off and gassed with dry hydrogen chloride at 5 to 10 °.
  • ketones can be used as starting products, for example.
  • the following example relates to the preparation of the y-azolyl alcohols according to the invention.
  • the active compounds according to the invention are used e.g. in the form of directly sprayable solutions, powders, suspensions, including high-proof aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active substances according to the invention.
  • mineral oil fractions of medium to high boiling points such as kerosene or diesel oil, also coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example loluene, xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols (for example methanol, butanol), amines (for example ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g.
  • natural stone powder e.g. kaolins, clays, talc, chalk
  • synthetic stone powder e.g.
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, leachate and methyl cellulose.
  • nonionic and anionic emulsifiers e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates
  • dispersants such as lignin, leachate and methyl cellulose.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • agents according to the invention can also be present in these application forms together with other active ingredients, e.g. Herbicides, insecticides, growth regulators and fungicides or even mixed with fertilizers.
  • active ingredients e.g. Herbicides, insecticides, growth regulators and fungicides or even mixed with fertilizers.
  • the active ingredients according to the invention are used in a favorable period of time, the exact determination of which depends on the geographical, climatic and vegetative conditions.
  • Tests were carried out in the greenhouse to test the biological activity of the new compounds.
  • the test plants were sown into plastic containers with a diameter of 12.5 cm using peat culture substrate which was sufficiently supplied with nutrients.
  • the active compounds are applied in aqueous solution or dispersion in different amounts to the soil on the day of sowing.
  • the substances were sprayed directly onto the surface of the floor.
  • the plants treated with the agents according to the invention showed a significantly lower growth in length than the untreated control, which could be confirmed by subsequent length measurements.
  • 100 plants from each treatment series were measured.
  • active ingredient 5 20 parts by weight of active ingredient 5 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • active ingredient 3 40 parts by weight of active ingredient 3 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid urea formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • active ingredient 4 20 parts of active ingredient 4 are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100725A 1977-08-27 1978-08-23 Gamma-Azolylalkohole, und ihre Verwendung zur Regulierung des Pflanzenwachstums Expired EP0000940B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19772738725 DE2738725A1 (de) 1977-08-27 1977-08-27 Azolylalkohole
DE2738725 1977-08-27
DE19772739352 DE2739352A1 (de) 1977-08-27 1977-09-01 Mittel zur regulierung des pflanzenwachstums

Publications (3)

Publication Number Publication Date
EP0000940A2 EP0000940A2 (de) 1979-03-21
EP0000940A3 EP0000940A3 (en) 1979-03-21
EP0000940B1 true EP0000940B1 (de) 1980-08-06

Family

ID=25772627

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100725A Expired EP0000940B1 (de) 1977-08-27 1978-08-23 Gamma-Azolylalkohole, und ihre Verwendung zur Regulierung des Pflanzenwachstums

Country Status (10)

Country Link
US (1) US4328028A (ja)
EP (1) EP0000940B1 (ja)
JP (2) JPS5444026A (ja)
AT (2) AT359096B (ja)
BE (1) BE870081A (ja)
CA (2) CA1111429A (ja)
DE (2) DE2738725A1 (ja)
FR (1) FR2401611A1 (ja)
GB (1) GB2003848B (ja)
NL (1) NL7808961A (ja)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2842801A1 (de) * 1978-09-30 1980-04-10 Basf Ag Beta-triazolyloxime
US4293561A (en) * 1979-03-09 1981-10-06 Syntex (U.S.A.) Inc. 1-(Naphthyl-n-propyl)imidazole derivatives
US4554007A (en) * 1979-03-20 1985-11-19 Sumitomo Chemical Company, Limited Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant
DE2920437A1 (de) * 1979-05-19 1980-11-27 Bayer Ag Geometrische isomere von 4,4- dimethyl-1-phenyl-2-(1,2,4-triazol-1-yl)- 1-penten-3-olen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2921168A1 (de) * 1979-05-25 1980-12-11 Basf Ag Triazolylderivate und verfahren zu ihrer herstellung sowie diese enthaltende mittel zur beeinflussung des pflanzenwachstums
DE2925687A1 (de) * 1979-06-26 1981-01-22 Basf Ag Triazolylglykolether enthaltende mittel zur regulierung des pflanzenwachstums
CH647513A5 (de) * 1979-11-13 1985-01-31 Sandoz Ag Triazol-derivate, deren herstellung und verwendung.
DE2948206A1 (de) 1979-11-30 1981-06-25 Basf Ag, 6700 Ludwigshafen Fungizide (gamma) -azolyl-verbindungen, ihre herstellung und verwendung
DE3011258A1 (de) * 1980-03-24 1981-10-01 Basf Ag, 6700 Ludwigshafen Fungizide mittel, enthaltend triazolylderivate und verfahren zur bekaempfung von pilzen mit ihnen
DE3019049A1 (de) * 1980-05-19 1981-12-03 Basf Ag, 6700 Ludwigshafen Neue azolverbindungen
DE3025879A1 (de) * 1980-07-09 1982-02-11 Basf Ag, 6700 Ludwigshafen 1,3-dioxan-5-yl-alkyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
DE3026140A1 (de) * 1980-07-10 1982-02-18 Basf Ag, 6700 Ludwigshafen 1,3-dioxan-5-yl-alkenyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
DE3215360A1 (de) * 1982-04-24 1983-10-27 Basf Ag, 6700 Ludwigshafen Bisazolyl-verbindungen, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
US4510148A (en) * 1982-06-12 1985-04-09 Pfizer Inc. 2-Heterocyclic-1,3-bis(1H-1,2,4-triazol-1-yl)-propan-2-ols as antifungal agents
DE3233145A1 (de) * 1982-09-07 1984-03-08 Basf Ag, 6700 Ludwigshafen Neopentyl-phenethyltriazole, verfahren zu ihrer herstellung und diese enthaltende fungizide
DE3511922A1 (de) 1985-04-01 1986-10-09 Basf Ag, 6700 Ludwigshafen Azolverbindungen, verfahren zu ihrer herstellung und mittel zur regulierung des pflanzenwachstums
DE3515309A1 (de) 1985-04-27 1986-10-30 Basf Ag, 6700 Ludwigshafen 1,3-dioxan-5-yl-alkyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
JPH034070A (ja) * 1989-06-01 1991-01-10 Minolta Camera Co Ltd 防水機構
EP0507966A4 (en) * 1990-11-02 1993-04-28 Sumitomo Chemical Company Limited Thermoplastic resin composition
JP2700510B2 (ja) * 1991-05-17 1998-01-21 明治製菓株式会社 植物生長調節剤ならびに植物のストレス抵抗性を増強する方法
US6156705A (en) * 1997-12-04 2000-12-05 Henkel Corporation Use of fatty alcohol polyalkoxy alkyl ethers in agricultural formulations
KR102386124B1 (ko) * 2015-10-02 2022-04-14 삼성전자주식회사 고분자 조성물, 고분자 조성물의 제조 방법, 전자기기 및 전자기기의 제조 방법

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Publication number Priority date Publication date Assignee Title
GB1569267A (en) * 1975-12-16 1980-06-11 Ici Ltd Substituted propiophenones and herbicidal and fungicidal compositions containing them
DE2624529A1 (de) * 1976-06-01 1977-12-22 Bayer Ag Aminomethylazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und zur regulierung des pflanzenwachstums
US4130409A (en) * 1976-06-08 1978-12-19 Imperial Chemical Industries Limited Triazolyl butandiones
DE2634511A1 (de) 1976-07-31 1978-02-02 Basf Ag Beta-azolylketone
DE2656728A1 (de) 1976-12-15 1978-06-29 Basf Ag Beta-imidazolylketone
US4181518A (en) * 1976-12-24 1980-01-01 Imperial Chemical Industries Limited Method of regulating plant growth using triazole and imidazole compounds
DE2706838A1 (de) * 1977-02-17 1978-08-24 Bayer Ag Mittel zur regulierung des pflanzenwachstums
DE2706670A1 (de) * 1977-02-17 1978-08-24 Basf Ag Metallkomplexe von beta-azolylketonen
GB1601453A (en) * 1977-05-05 1981-10-28 Ici Ltd Triazole and imidazole derivatives useful in agriculture

Also Published As

Publication number Publication date
FR2401611B1 (ja) 1983-09-09
AT359096B (de) 1980-10-27
US4328028A (en) 1982-05-04
ATA621378A (de) 1980-03-15
ATA632478A (de) 1980-01-15
GB2003848B (en) 1982-03-17
NL7808961A (nl) 1979-03-05
CA1111429A (en) 1981-10-27
EP0000940A2 (de) 1979-03-21
JPS5449328A (en) 1979-04-18
DE2738725A1 (de) 1979-03-08
GB2003848A (en) 1979-03-21
CA1111430A (en) 1981-10-27
BE870081A (fr) 1979-02-28
EP0000940A3 (en) 1979-03-21
DE2739352A1 (de) 1979-03-15
AT358079B (de) 1980-08-25
FR2401611A1 (fr) 1979-03-30
JPS5444026A (en) 1979-04-07

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