EP0000528A1 - Esters organiques d'acide phosphorique, procédé pour leur préparation et leur application comme insecticides, acaricides et nématocides - Google Patents

Esters organiques d'acide phosphorique, procédé pour leur préparation et leur application comme insecticides, acaricides et nématocides Download PDF

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Publication number
EP0000528A1
EP0000528A1 EP78100412A EP78100412A EP0000528A1 EP 0000528 A1 EP0000528 A1 EP 0000528A1 EP 78100412 A EP78100412 A EP 78100412A EP 78100412 A EP78100412 A EP 78100412A EP 0000528 A1 EP0000528 A1 EP 0000528A1
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EP
European Patent Office
Prior art keywords
spp
general formula
chloride
carbon atoms
given above
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
EP78100412A
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German (de)
English (en)
Other versions
EP0000528B1 (fr
Inventor
Junichi Saito
Akio Kudamatsu
Toyohiko Kume
Shinichi Tsuboi
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 CropScience KK
Original Assignee
Nihon Tokushu Noyaku Seizo KK
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Publication date
Application filed by Nihon Tokushu Noyaku Seizo KK filed Critical Nihon Tokushu Noyaku Seizo KK
Publication of EP0000528A1 publication Critical patent/EP0000528A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention relates to new organic phosphoric acid esters, a process for their preparation and their use as insecticides, acaricides and nematocides.
  • the compounds of formula (I) have been found to have excellent insecticidal, acaricidal and nematocidal activity.
  • R 1 is preferably alkyl with 1 to 3 carbon atoms (in particular methyl, ethyl or n-propyl), R 2 alkyl with 3 or 4 carbon atoms (in particular n-propyl, n-butyl, sec-butyl or isobutyl) or alkoxyalkyl with 3 to 6 carbon atoms (especially 2- (C 1 -C 4 alkoxy) ethyl such as methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl or n-butoxyethyl),
  • X denotes hydrogen, trihalomethyl (especially trichloromethyl or trifluoromethyl) or alkoxy with 1 to 4 carbon atoms (especially ethoxy) and Y fluorine or chlorine.
  • Examples of the thiophosphoryl halides of the general formula (II) which are suitable as starting compounds in process variant (a) are O-methyl-Sn-propylphosphoric chloride thioate, 0-ethyl-Sn-propyl phosphorus chloride: ° thioate, 0, S-di-n-propylphosphoric chloride thioate O-ethyl-Sn-butylphosphoric chloride thioate, 0-ethyl-S-isobutylphosphoric chloride thioate, O-ethyl-S-sec.butylphosphoric chloride thioate, O-ethyl-S-methoxyethylphosphoric chloride thioate, O-ethyl-S-ethoxythioethylphosphorus chloride äthylphosphorchloridthioat, O- ⁇ thyl-S-isopropoxyäthylphosphorchloridthioat and O
  • alcohols and alcoholates of the general formula (III) which are suitable as starting materials in process variant (a) are 2,2,2-trifluoroethanol, 2,2,2-trichloroethanol, 1,1,1,3,3,3-hexafluoro 2-propanol, 1,1,1,3,3,3-hexachloro-2-propanol and 1-ethoxy-2,2,2-trifluoroethanol and the sodium or potassium salts of these alcohols.
  • Suitable thiophosphoryl halides of the general formula (IV) as starting compounds in process variant (b) are 0-2,2,2-trifluoroethyl-Sn-propylphosphoric chloride thioate, 0-2,2,2-trichloroethyl-Sn-propylphosphoric chloride thioate, 0-1 , 1,1,3,3,3-hexafluoro-2-propyl-Sn-propylphosphoric chloride thioate, 0-1,1,1,3,3,3-hexachloro-2-propyl-Sn-propylphoaphorchloride thioate, 0-2.2 , 2-trifluoroethyl-Sn-butylphosphoric chloride thioate, 0-2,2,2-trichloroethyl-Sn-butylphosphoric chloride thioate, 0-1,1,1,3,3,3-hexafluoro-2-propyl-Sn-butylphosphoric chloride thioate
  • alcohols and alcoholates of the general formula (v) which can be used as starting compounds in process variant (b) are methanol, ethanol and n-propanol and the sodium or potassium salts of these alcohols.
  • reaction can be represented by the following scheme:
  • phosphites of the general formula (VI) which are suitable in process variant (c) are O-methyl-0-2,2,2-trifluoroethylphosphite, 0-methyl-0-2,2,2-trichloroethylphosphite, O-ethyl-O -1,1,1,3,3,3-hexafluoro-2-propyl phosphite, O-ethyl-0-1,1,1,3,3,3-hexachlor-2-propyl-phosphite, O-ethyl-0 -1-ethoxy-2,2,2-trifluoroethyl phosphite, on-propyl-0-2,2,2-trifluoroethyl phosphite, O-ethyl-O,? ,, 2,2-trifluoroethyl phosphite and O-ethyl-0.2, 2,2-trichloroethyl phosphite.
  • sulfenyl halides of the general formula (VII) which are suitable as starting compounds in process variant (c) are 1-propanesulfenyl chloride, 1-butanesulfenyl chloride, isobutanesulfenyl chloride, 2-butanesulfenyl chloride, methoxyethanesulfenyl chloride, ethoxy-ethanesulfenyl chloride, n-propoxy-ethanesulfonyl chloride and n-propenyl chloride and called the corresponding bromine salts,
  • Each of the sulfenyl chlorides or bromides can easily be prepared by a conventional method which consists in reacting the corresponding disulfide with chlorine, bromine, sulfuryl chloride or sulfuryl bromide.
  • reaction can be represented by the following scheme:
  • the reaction according to variants (a), (b) and (c) of the process according to the invention can be carried out in the presence of an acid binder.
  • suitable acid binders are the hydroxides, carbonates, bicarbonates and alcoholates of the alkali metals and tertiary amines such as e.g. Triethylamine, diethylaniline or pyridine.
  • the end product can also be obtained according to process variant (a) or (b) with good yield and high degree of purity if one works without an acid binder and instead thiophosphoryl halide of the formula (II) or (IV) with an alkali metal alcoholate of the formula (III) or (V) implements.
  • Process variants (a), (b) and (c) according to the invention are preferably carried out using a solvent or diluent.
  • solvents or diluents are water and inert organic solvents such as aliphatic, alicyclic and aromatic hydrocarbons (which may or may not be chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride , Trichlorethylene and chlorobenzene; Ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, propylene oxide, dioxane and tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl
  • Variants (a), (b) and (c) of the process according to the invention can be carried out within a wide temperature range.
  • the process is carried out at temperatures from -20 ° C. to the boiling point of the mixture, preferably at 0-100 ° C.
  • the reaction is expediently carried out at atmospheric pressure, but it can also be carried out at elevated or reduced pressure.
  • the compounds according to the invention have excellent insecticidal, acaricidal and nematocidal activity. They can therefore be used to control plant pests and those pests which occur in the hygiene sector and in the supply or material protection sector and combine low phytotoxicity with good activity against stinging and biting insects and mites.
  • the compounds according to the invention can be used with great success as pesticides in the fields of crop protection, the hygiene sector and the protection of stored products.
  • the compounds according to the invention can also be used in the field of veterinary medicine, since they are effective against animal parasites, in particular ectoparasites such as e.g. parasitic fly larvae are effective.
  • Plant parasites among the nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp ..
  • the active ingredients can be in the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed treatment powders, natural and synthetic materials impregnated with active ingredients, very fine Capsules in polymeric substances, seed coating compositions and formulations intended for use in fumigation equipment, such as fumigation cartridges, canisters and snakes, as well as in ULV cold mist and warm mist formulations.
  • the formulations can be prepared by known methods, i.e. e.g. by mixing the active ingredients with extenders, i.e. liquid or liquefied, gaseous or solid diluents or carriers, optionally using surfactants, i.e. Emulsifiers and / or dispersants and / or foaming agents are produced. If water is used as an extender, organic solvents can e.g. can also be used as auxiliary solvents.
  • extenders i.e. liquid or liquefied, gaseous or solid diluents or carriers
  • surfactants i.e. Emulsifiers and / or dispersants and / or foaming agents are produced.
  • organic solvents can e.g. can also be used as auxiliary solvents.
  • aromatic hydrocarbons such as e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic or alicyclic hydrocarbons such as e.g. Cyclohexane or paraffins such as Petroleum fractions, alcohols such as e.g. Butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone or strongly polar solvents such as e.g. Dimethylformamide and dimethyl sulfoxide and water are suitable.
  • aromatic hydrocarbons such as e.g. Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene
  • Liquefied, gaseous diluents or carriers are to be understood as liquids which are gaseous at normal temperatures and pressure, e.g. Blowing agents for aerosols, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Ground solid minerals such as e.g. Kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly disperse silica, aluminum oxide and silicates are suitable.
  • Crushed and broken natural rocks such as e.g. Calcite, marble, pumice, sepiolite and dolomite, synthetic granules from inorganic and organic flours and the granules of organic materials such as Sawdust or sawdust, coconut shells, corn cobs and tobacco stems can be used.
  • Non-ionic or anionic emulsifiers such as e.g. Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysis products are used.
  • Suitable dispersants are e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as e.g. Carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices such as Gum arabic, polyvinyl alcohol and polyvinyl acetate can be used.
  • Colorants such as inorganic pigments, e.g. Iron oxide, titanium oxide and Prussian blue and organic dyes such as Alizarin dyes, azo dyes or metal phthalocyanine dyes and trace nutrients such as the salts of iron, manganese, boron, copper, cobalt, olybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide and Prussian blue
  • organic dyes such as Alizarin dyes, azo dyes or metal phthalocyanine dyes and trace nutrients such as the salts of iron, manganese, boron, copper, cobalt, olybdenum and zinc are used.
  • the active compounds according to the invention can in the Formulations mixed with other active ingredients such as, for example, fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth regulators, plant nutrients and agents which improve soil structure can be used.
  • active ingredients such as, for example, fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth regulators, plant nutrients and agents which improve soil structure can be used.
  • the formulations generally contain 0.1-95% by weight, preferably 0.5-90% by weight, of active ingredient.
  • the active compounds according to the invention can be used in the form of commercially available formulations or preparations prepared from these formulations.
  • the active substance content of the commercially available formulations can vary within a wide range.
  • the active substance concentration in the formulations used can be 0.0001-20% by weight, preferably 0.005-10% by weight, of active substance.
  • the active compounds can be used according to conventional processes suitable for the form of use in question.
  • the present invention also relates to an insecticidal, acaricidal or nematicidal composition which, as an active ingredient, mixes a compound according to the invention and contains a solid or liquefied, gaseous diluent or carrier or mixed with a liquid diluent or carrier containing a surfactant.
  • the invention also relates to a method for Control of insects, acarids or nematodes, which consists in applying a compound according to the invention, alone or in the form of a composition which contains a compound according to the invention mixed with a diluent or carrier, to the insects, acarids or nematodes or to their habitat becomes.
  • crops are obtained as arable products which are protected from damage by inks, acarids or nematodes by being drawn in areas to which a compound according to the invention alone or mixed before and / or during the growth of the plants is applied with a diluent or carrier.
  • insecticidal, acaricidal and nematocidal activity of the compounds according to the invention can be seen from the bioassay examples below.
  • the compounds according to the invention are each designated by the number (in parentheses) of the corresponding preparation example, which is mentioned later in the description.
  • Emulsifier polyoxyethylene alkyl paenyl ether 1 part by weight
  • Sweet potato leaves were dipped in an aqueous formulation containing a predetermined amount of active ingredient.
  • the leaves are air dried and then placed in a 9 cm diameter petri dish. 10 larvae of the Spodoptere litura in the third stage of development are then placed in the Petri dish. The shell is kept in a climatic chamber at 28 ° C, after 24 hours the number of dead larvae is determined and the mortality rate is calculated. The results are shown in Table A.
  • a filter paper is placed in a 9 cm diameter petri dish. Then 1 ml of an aqueous formulation, which was prepared according to Example A and has a predetermined active ingredient concentration, is introduced into the dish. 20 copies of the Callosobruchus chinensis are placed in the Petri dish and the dish is kept in a climatic chamber at 28 ° C for 24 hours. After this period, the kill rate is determined.
  • Rice plants about 10 cm high are planted in pots with a diameter of 12 cm.
  • An aqueous preparation which contains a predetermined concentration of active ingredient in the formulation prepared according to Example A is applied to the rice plants in amounts of 10 ml per pot. After the applied preparation has dried, wire mesh cages, each 7 cm in diameter and 14 cm in height, are placed over the pots, and 30 female adults of Nephotettix cincticeps, which is resistant to organophosphorus preparations, are used in each cage. The pots are then placed in a climatic chamber. After 24 hours, the number of dead insects was determined and the kill rate calculated. The results are shown in Table C.
  • a filter paper was placed in a Petri dish 9 cm in diameter and with 1 ml of an aqueous Prerate, which was prepared according to Example A has a predetermined concentration of active ingredient, soaked. Da.nn 10 female adults of the Musca domestica resistant to organophosphorus preparations were introduced into the shell. The dish was kept in a climatic chamber at 28 ° C for 24 hours, after which time the number of dead flies was determined and the kill rate was calculated. The results are shown in Table D.
  • a filter paper was placed in a Petri dish with a diameter of 9 cm and impregnated with 1 ml of an aqueous preparation which had been prepared according to Example A and had a predetermined active ingredient concentration. 10 adults of the Blatella germanica were placed in the bowl, which was kept in a climatic chamber at 28 ° C for 24 hours, after which the number of dead insects was determined and the kill rate calculated. The results are shown in Table G.
  • An active ingredient preparation was prepared by pulverizing and mixing 2 parts by weight of active ingredient and 98 parts of talc.
  • Substance preparation was introduced into soil that had been inoculated with Meloidogyne incognita acrita in such amounts that concentrations of 50, 25 or 10 or, 5 ppm resulted. Soil and active ingredient were mixed uniformly with stirring and then placed in pots with an area of 0.0002 a each. About 20 seeds of the Kurihara tomato variety per pot were sown into the soil treated in this way. The tomato seeds were grown in a greenhouse. After four weeks, the plants were pulled from the soil without damaging the roots, the degree of infestation on 10 selected roots was rated on the following scale in order to determine a root node index:

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100412A 1977-07-25 1978-07-17 Esters organiques d'acide phosphorique, procédé pour leur préparation et leur application comme insecticides, acaricides et nématocides Expired EP0000528B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP88352/77 1977-07-25
JP52088352A JPS6021159B2 (ja) 1977-07-25 1977-07-25 有機リン酸エステル系化合物、該化合物の製造方法および該化合物を有効成分として含有する殺虫、殺ダニおよび殺センチユウ剤

Publications (2)

Publication Number Publication Date
EP0000528A1 true EP0000528A1 (fr) 1979-02-07
EP0000528B1 EP0000528B1 (fr) 1980-07-23

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ID=13940419

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Application Number Title Priority Date Filing Date
EP78100412A Expired EP0000528B1 (fr) 1977-07-25 1978-07-17 Esters organiques d'acide phosphorique, procédé pour leur préparation et leur application comme insecticides, acaricides et nématocides

Country Status (23)

Country Link
US (1) US4189476A (fr)
EP (1) EP0000528B1 (fr)
JP (1) JPS6021159B2 (fr)
AR (1) AR220719A1 (fr)
AT (1) AT360276B (fr)
AU (1) AU517310B2 (fr)
BR (1) BR7803517A (fr)
CA (1) CA1110650A (fr)
CS (1) CS199738B2 (fr)
DD (1) DD138878A5 (fr)
DE (1) DE2860061D1 (fr)
DK (1) DK328078A (fr)
EG (1) EG13377A (fr)
ES (3) ES471989A1 (fr)
HU (1) HU182737B (fr)
IL (1) IL55198A (fr)
IT (1) IT1099576B (fr)
OA (1) OA06034A (fr)
PL (3) PL114565B1 (fr)
PT (1) PT68318A (fr)
SU (1) SU786850A3 (fr)
TR (1) TR19961A (fr)
ZA (1) ZA784182B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU589458B2 (en) * 1985-10-07 1989-10-12 American Cyanamid Company Improved shape for extruded catalyst support particles and catalysts
EP0391131A3 (fr) * 1989-04-03 1991-06-12 Bayer Ag Esters fluoroalkylés d'acide thiophosphorique
EP0507189A3 (en) * 1991-04-05 1993-02-24 Bayer Ag 0-(2-fluoroalkyl)-s-alkyl-(di)thiophosphoric(phosphonic)-acid esters, process for their preparation and their use as pesticides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5788414A (en) * 1980-11-21 1982-06-02 Seiko Epson Corp Alignment device
US6620362B1 (en) * 2002-06-14 2003-09-16 Nan Ya Plastics Corporation Method of manufacturing polyester fiber having improved light fastness

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359846A1 (fr) * 1976-07-27 1978-02-24 Nihon Tokushu Noyaku Seizo Kk Nouveaux phosphorothiolates ou phosphorothionothiolates de o-ethyle, s-n-propyle et 0-2,2,2-trihalogenethyle, leur procede de preparation et leur application comme insecticides, acaricides et nematicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3184377A (en) * 1961-12-12 1965-05-18 Chemagro Corp Method of killing nematodes with thiophosphates
DD107581A1 (fr) * 1973-05-02 1974-08-12

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359846A1 (fr) * 1976-07-27 1978-02-24 Nihon Tokushu Noyaku Seizo Kk Nouveaux phosphorothiolates ou phosphorothionothiolates de o-ethyle, s-n-propyle et 0-2,2,2-trihalogenethyle, leur procede de preparation et leur application comme insecticides, acaricides et nematicides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU589458B2 (en) * 1985-10-07 1989-10-12 American Cyanamid Company Improved shape for extruded catalyst support particles and catalysts
EP0391131A3 (fr) * 1989-04-03 1991-06-12 Bayer Ag Esters fluoroalkylés d'acide thiophosphorique
EP0507189A3 (en) * 1991-04-05 1993-02-24 Bayer Ag 0-(2-fluoroalkyl)-s-alkyl-(di)thiophosphoric(phosphonic)-acid esters, process for their preparation and their use as pesticides

Also Published As

Publication number Publication date
DD138878A5 (de) 1979-11-28
AT360276B (de) 1980-12-29
AR220719A1 (es) 1980-11-28
PT68318A (de) 1978-08-01
CS199738B2 (en) 1980-07-31
JPS5424829A (en) 1979-02-24
IL55198A0 (en) 1978-09-29
ES479025A1 (es) 1979-07-01
US4189476A (en) 1980-02-19
IT7825985A0 (it) 1978-07-21
IL55198A (en) 1982-12-31
JPS6021159B2 (ja) 1985-05-25
HU182737B (en) 1984-03-28
ES479024A1 (es) 1979-07-01
DK328078A (da) 1979-01-26
PL114583B1 (en) 1981-02-28
OA06034A (fr) 1981-06-30
TR19961A (tr) 1980-05-16
SU786850A3 (ru) 1980-12-07
IT1099576B (it) 1985-09-18
AU517310B2 (en) 1981-07-23
PL114565B1 (en) 1981-02-28
PL119038B1 (en) 1981-11-30
CA1110650A (fr) 1981-10-13
EP0000528B1 (fr) 1980-07-23
PL208574A1 (fr) 1980-01-02
ATA540178A (de) 1980-05-15
AU3828578A (en) 1980-01-31
ES471989A1 (es) 1979-10-01
ZA784182B (en) 1979-07-25
BR7803517A (pt) 1979-03-20
DE2860061D1 (en) 1980-11-13
EG13377A (en) 1982-09-30

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