EP0000030B1 - Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide - Google Patents

Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide Download PDF

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Publication number
EP0000030B1
EP0000030B1 EP78100050A EP78100050A EP0000030B1 EP 0000030 B1 EP0000030 B1 EP 0000030B1 EP 78100050 A EP78100050 A EP 78100050A EP 78100050 A EP78100050 A EP 78100050A EP 0000030 B1 EP0000030 B1 EP 0000030B1
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EP
European Patent Office
Prior art keywords
carbon atoms
diurethane
formula
parts
weight
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
EP78100050A
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German (de)
English (en)
French (fr)
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EP0000030A1 (de
Inventor
Ulrich Dr. Schirmer
Bruno Dr. Wuerzer
Wolfgang Dr. Rohr
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
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0000030A1 publication Critical patent/EP0000030A1/de
Application granted granted Critical
Publication of EP0000030B1 publication Critical patent/EP0000030B1/de
Expired legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00—Assemblies consisting of a plurality of semiconductor or other solid state devices
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • the present invention relates to valuable sulfur-containing diurethanes with excellent herbicidal activity, herbicides which contain these compounds, and processes for controlling unwanted plant growth with these compounds.
  • the new diurethanes have the general formula in the Z the rest and Y the rest means, where Z is always different from Y and R 1 and R 2 each independently of one another hydrogen, alkyl having 1 to 4 carbon atoms (eg methyl, ethyl, isopropyl), alkoxyalkyl having 2 to 4 carbon atoms (eg methoxymethyl, 2-methoxyethyl) ), Alkoxycarbonylalkyl with 3 to 5 carbon atoms (e.g. methoxycarbonylmethyl), haloalkyl with 1 to 4 carbon atoms (e.g.
  • R 3 and R 4 each independently of one another unsubstituted alkyl with 1 to 6 carbon atoms or halogen or alkoxy with 1 to 2 carbon atoms or alkoxycarbonyl or halogen substituted or unsubstituted phenyl substituted alkyl with 1 to 4 carbon atoms (e.g.
  • benzyl isopropyl, n- Propyl, 4- x chlorobenzyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2,4-dichlorobenzyl, 2-phenylethyl) or alkenyl with 2 to 4 K.
  • hydrogen atoms e.g. allyl butene (1) yl (3)
  • alkynyl with 3 to carbon atoms e.g.
  • cycloalkyl with 5 to 8 carbon atoms optionally substituted by alkyl with 1 to 4 carbon atoms e.g. cyclopentyl, cyclohexyl, 3-methylcyclohexyl, 2,6-dimethylcyclohexyl, cycloheptyl, 4-tert-butylcyclohexyl, 3,5-dimethylcyclohexyl
  • bicycloalkyl with 7 to 8 carbon atoms e.g. norbonyl
  • tricycloalkyl with 10 to 15 carbon atoms e.g.
  • Tricyclo (4,3,1, 2.5 O 1.6 ) -decyl a phenyl radical with a fused ring system (e.g. naphthyl or indyl), phenyl or a mono- or polysubstituted phenyl radical, with the substituents alkyl having 1 to 4 carbon atoms, halogen or Alkoxy with 1 to 3 carbon atoms, mean (for example phenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methylphenyl, 2-fluorophenyl, 3-methyl-5-isopropylphenyl, 3-ethylphenyl, 3-chlorophenyl, 2,4,6 -Trimethylphenyl, 3-fluorophenyl, 3-chloro-4-fluorophenyl, 3,4-dimethylphenyl, 4-methylp henyl, 3,4-difluorophenyl, 3-chloro-4-methylphenyl 3-bromophenyl,
  • n 1 to 4 and A, B, D, E each independently represent oxygen or sulfur, where not all radicals A, B, D, E simultaneously represent oxygen and where at least one of these radicals always means sulfur, a good herbicidal action against numerous important unwanted plants (e.g. Euphorbia and Chenopodium) and at the same time have a good tolerance for many crops (e.g. cotton and corn). These effects are better than those of the known active ingredients.
  • the new connections can be made, for example, using the following methods, where the radicals A, B, D, E, R, R 1 , R 2 , R 3 , R 4 , X and n have the meaning given above.
  • urethanes and chloroformic acid esters in the following, these two collective terms are also to be understood as meaning thionothio- and dithiourethanes as well as chloroformic acid urethionoesters, chloroformic acid thioesters and chloroformic acid dithioesters.
  • meta-nitrophenyliso (thio) cyanates B
  • B meta-nitrophenyliso (thio) cyanates
  • the aminourethanes F can also be obtained by reacting meta-phenylenediamines (D) with chloroformic acid esters.
  • Another synthesis possibility is the reaction of aryl-1,3-diiso (thio) cyanates (E) with only one mole of component R 3 -BH, which leads to the iso (thio) cyanatourethanes (G) (JA Parker, JJ Thomas and CL Zeise, J. org. Chem. 22, 594 to 596 (1957)), which can also be obtained by (thio) phosgenation of the aminourethanes (F) (DT-OS 19 14 270, page 5, example 8). Subsequent reaction with component R 4 DH leads to the desired end products. Basically, it should be noted that the order of the -CABR 3 or -EDR 4 groupings is arbitrary.
  • connection has the following structural formula:
  • connection has the following structural formula:
  • connection has the following structural formula:
  • aminourethanes (F) can be prepared by appropriate processes:
  • connection has the following structural formula:
  • a mixture of 20 parts by weight of N- (3-isothiocyanatophenyl) -O-methylcarbamate (obtainable from N- (3-aminophenyl) -0-methylcarbamate and thiophosgene, mp. 99-100 ° C., 20 parts by weight of methanol, 3 parts by weight of triethylamine and 150 parts by weight of toluene are boiled for 6 hours, after which the mixture is recrystallized from toluene: mp 147-149 ° C. (No. 2).
  • connection has the following structural formula:
  • connection has the following structural formula:
  • 3-methoxycarbonylaminophenyl-N- (3'-methyl-phenyl) -carbamate and 3-ethylcarbonylaminophenyl-N-phenylcarbamate are characterized by their, albeit different, activity against broad-leaved unwanted plants with a considerable degree of tolerance for Sugar beet.
  • 3-methoxycarbonylaminophenyl-N- (3'-methylphenyl) carbamate has an even more favorable selectivity in this culture than the second compound of this type mentioned above.
  • 3-Isopropyl-2,1,3-benzothiadiazinon (4) -2,2-dioxide has a completely different field of application. This compound is used to control various broad-leaved weeds in soybeans, peanuts, cereals, corn and some types of vegetables. However, there are still gaps in effectiveness here.
  • 3-methoxycarbonylaminophenyl-N- (3'methyl-phenyl) carbamate hardly shows at for its class good herbicidally active crop selectivity, which is why the connection example for soybeans was recommended only for sub-leaf spraying (post- di re cted) (Arndt, F and G Boroschewsky; New Selective Herbicides - VIII International Plant Protection Congress, Reports and Information, Section 111 Chemical Control, Part I, Moskow 1975, pp. 42-4.9).
  • the young shoots and leaves of the crop plants should not be hit by the spray mixture, but undesirable plants that are located underneath them.
  • Plastic flower pots with a content of 300 cm 3 were filled with loamy sand and equipped with the test plants according to species. This mainly involves sowing seeds or transplanting vegetatively propagated species.
  • the active ingredients were suspended or emulsified in water as a distribution medium and sprayed onto the leaves of the test plants and the still exposed soil surface using fine-spreading nozzles in post-emergence application.
  • the plants were first grown to a height of 3 to 10 cm in the test vessels, depending on the growth habit, and then treated.
  • the temperature requirements of the test plants were met by placing them in cooler or warmer sections of the greenhouse systems.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their reaction to the individual treatments evaluated.
  • the application rates of the test substances are considered to be kg / ha of active substance.
  • the agents according to the invention or mixtures containing them can be used in a further large number of crops to eliminate undesired plant growth in addition to the useful plants listed in the tables.
  • the application concentrations can range from 0.1 to 15 kg / ha and more, depending on the control object.
  • the new compounds can be mixed with one another or numerous other herbicidal or growth-regulating compounds can be used as mixing and combination partners.
  • wetting agents and adhesives as well as non-phytotoxic oils can be added.
  • the application is e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules, by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, are used to produce directly sprayable solutions, emulsions, pastes and oil dispersions.
  • strongly polar solvents e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. into consideration.
  • Aqueous application forms can be prepared from emulsion concentrations, pastes or wettable powders (wettable powders), oil dispersions by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • surfactants are: alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth metal salts, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite
  • the formulations contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 percent by weight.
  • active ingredient 7 40 parts by weight of active ingredient 7 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 2 20 parts 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.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Power Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP78100050A 1977-06-03 1978-06-01 Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide Expired EP0000030B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772725146 DE2725146A1 (de) 1977-06-03 1977-06-03 Diurethane und herbizide
DE2725146 1977-06-03

Publications (2)

Publication Number Publication Date
EP0000030A1 EP0000030A1 (de) 1978-12-20
EP0000030B1 true EP0000030B1 (de) 1980-12-10

Family

ID=6010672

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100050A Expired EP0000030B1 (de) 1977-06-03 1978-06-01 Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide

Country Status (24)

Country Link
EP (1) EP0000030B1 (enrdf_load_stackoverflow)
JP (1) JPS543038A (enrdf_load_stackoverflow)
AT (1) AT358869B (enrdf_load_stackoverflow)
AU (1) AU519196B2 (enrdf_load_stackoverflow)
BR (1) BR7803528A (enrdf_load_stackoverflow)
CA (1) CA1110264A (enrdf_load_stackoverflow)
CS (1) CS196429B2 (enrdf_load_stackoverflow)
DD (1) DD135853A5 (enrdf_load_stackoverflow)
DE (2) DE2725146A1 (enrdf_load_stackoverflow)
DK (1) DK247278A (enrdf_load_stackoverflow)
ES (1) ES470367A1 (enrdf_load_stackoverflow)
FI (1) FI781762A7 (enrdf_load_stackoverflow)
HU (1) HU177551B (enrdf_load_stackoverflow)
IE (1) IE46905B1 (enrdf_load_stackoverflow)
IL (1) IL54779A (enrdf_load_stackoverflow)
IT (1) IT1104710B (enrdf_load_stackoverflow)
NO (1) NO781931L (enrdf_load_stackoverflow)
NZ (1) NZ187460A (enrdf_load_stackoverflow)
PL (1) PL106564B1 (enrdf_load_stackoverflow)
PT (1) PT68091A (enrdf_load_stackoverflow)
SU (1) SU725541A3 (enrdf_load_stackoverflow)
TR (1) TR20048A (enrdf_load_stackoverflow)
YU (1) YU132578A (enrdf_load_stackoverflow)
ZA (1) ZA783163B (enrdf_load_stackoverflow)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3113449A1 (de) * 1981-04-03 1982-11-11 Hoechst Ag, 6000 Frankfurt "thiocarbaminsaeureester, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und ihre verwendung"
JPS5951205A (ja) * 1982-06-23 1984-03-24 Toyo Soda Mfg Co Ltd カ−バメ−ト誘導体を含有する除草剤
DE19800531A1 (de) * 1998-01-09 1999-07-15 Bayer Ag Verfahren zur Herstellung von N-(3-Amino-4-fluor-phenyl)-sulfonsäureamiden, N-(3-Amino-4-fluor-phenyl)-carbonsäureamiden und N-(3-Amino-4-fluor-phenyl)-carbamaten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1037578B (it) * 1975-04-23 1979-11-20 Snam Progetti Procedimento per la sintesi di esteri di acidi tiocarbammici
JPS537474A (en) * 1976-07-12 1978-01-23 Tsuneto Yoshii Process for producing soil conditioner and fertilizers from waste woods of artificial bed log for shiitake* shiitake aseptic timber and other edible or medicinal fungi culture base

Also Published As

Publication number Publication date
PL207278A1 (pl) 1979-03-26
SU725541A1 (ru) 1980-03-30
CA1110264A (en) 1981-10-06
IL54779A (en) 1982-12-31
SU725541A3 (en) 1980-03-30
BR7803528A (pt) 1979-02-20
AT358869B (de) 1980-10-10
FI781762A7 (fi) 1978-12-04
IT7849686A0 (it) 1978-06-02
NZ187460A (en) 1980-11-28
AU3657678A (en) 1979-12-06
PT68091A (fr) 1978-05-31
DE2860287D1 (en) 1981-02-19
AU519196B2 (en) 1981-11-19
ATA403178A (de) 1980-02-15
TR20048A (tr) 1980-07-02
DD135853A5 (de) 1979-06-06
ZA783163B (en) 1979-07-25
IL54779A0 (en) 1978-07-31
JPS6151583B2 (enrdf_load_stackoverflow) 1986-11-10
PL106564B1 (pl) 1979-12-31
IT1104710B (it) 1985-10-28
DK247278A (da) 1978-12-04
IE46905B1 (en) 1983-11-02
ES470367A1 (es) 1979-09-16
YU132578A (en) 1983-01-21
DE2725146A1 (de) 1978-12-14
NO781931L (no) 1978-12-05
IE781065L (en) 1978-12-03
CS196429B2 (en) 1980-03-31
JPS543038A (en) 1979-01-11
HU177551B (en) 1981-11-28
EP0000030A1 (de) 1978-12-20

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