PL136683B1 - Method of obtaining derivatives of phenoxybenzoic acid - Google Patents

Method of obtaining derivatives of phenoxybenzoic acid Download PDF

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Publication number
PL136683B1
PL136683B1 PL1982237639A PL23763982A PL136683B1 PL 136683 B1 PL136683 B1 PL 136683B1 PL 1982237639 A PL1982237639 A PL 1982237639A PL 23763982 A PL23763982 A PL 23763982A PL 136683 B1 PL136683 B1 PL 136683B1
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formula
reaction
temperature
solvent
sulfonamide
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PL1982237639A
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PL237639A1 (en
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Rhone Poulenc Agrochimie
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Publication of PL237639A1 publication Critical patent/PL237639A1/xx
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    • 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
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
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    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/52—Y being a hetero atom
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    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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Description

Przedmiotem wynalazku jest udoskonalony sposób wytwarzania niektórych pochodnych kwasów fenoksy- benzoesowych z grupa sulfonamidowa majacych wlasciwosci chwastobójcze.Chwastobójcze pochodne kwasów fenoksybenzoesowych z grupa sulfonamidowa sa znane z europejskich opisów patentowych nr nr 3416 i 23392. Opisane w tych opisach zwiazki oraz ich sole przedstawione sa wzorem 1, w którym A oznacza wodór, fluor, chlor, brom, jod, grupe nitrowa, -N=NCF3, P03H2 oraz jego estry alkilowe o 1^4 atomach wegla, NH2 NHOH, N2, grupe karboksylowa lub jedna z jej funkcyjnych pochodnych, grupe jedno- lub dwualkiloaminowa, grupe NH-CO-R1, w której R1 stanowi rodnik alkilowy albo grupa alko¬ ksylowa lub jednoalkiloaminowa albo dwualkiloaminowa, rodnik alkilowy, rodnik trójalkiloamoniowy, NHS02R2, w której R2 jest rodnikiem alkilowym lub fenylowym, NHCONHS02R2, w której R2 ma znaczenie wyzej podane, grupe alkilotio, alkilosulfinylowa, alkilosulfonylowa, dwualkilosulfoniowa, cyjanosulfonylowa, hydroksylowa, alkanoiloksylowa, alkoksylowa, alkoksylowa podstawiona rodnikiem alkoksykarbonylowym, SH, nitrozowa, -SCN, azydkowa, CF3, -N=N-P-/OCH3/2, rodnik acylowy, zas B oznacza wodór, fluor, chlor, O brom, jod, lub rodnik alkilowy, grupe alkoksylowa, alkilosulfinylowa, alkilosulfonylowa, CF3, N02 CN, NH2, NHCOR1, w której R1 jest okreslone jak powyzej lub CONH2 a G oznacza wodór lub chlorowiec albo rodnik alkilowy lub grupe dwualkiloaminowa oraz D oznacza fluor, chlor, brom, jod, grupe CF3, alkilotio, alkilosulfiny¬ lowa, alkilosulfonylowa, rodnik chlorowcoalkilowy, sulfamoilowy, formylowy, alkilokarbonylowy, CN lub grupe dwumetyloaminowa zas E stanowi wodór lub rodnik chlorowcoalkilowy, grupa alkoksylowa, alkilosulfinylowa, alkilosulfonylowa, CN, CF3, NH2, CONH2, NH-CO-R1, w której R1 ma znaczenie powyzej podane aFma jedno ze znaczen podanych dla B zas R jest grupa -CON/R4/S02R3, w którym to wzorze R4 oznacza wodór lub rodnik alkilowy o 1-4 atomach wegla a R3 oznacza rodnik fenylowy, pirydylowy lub tienylowy ewentualnie podstawiony jednym lub kilkoma atomami chlorowca, albo rodnikami alkilowymi lub grupami nitrowymi, albo tez oznacza rodnik alkenylowy lub alkinylowy o 2—4 atomach wegla lub rodnik alkilowy o 1 —4 atomach wegla ewentualnie podstawiony jednym lub kilkoma atomami fluoru, chloru, bromu albo jodu, korzystnie CF3 lub jednym, albo kilkoma sposród nastepujacych podstawników: grupa karboksylowa, rodnik alkoksykarbonylowy o 2-5 atomach wegla, alkilokarbonylowy o 2—5 atomach wegla jedno- lub dwualkilokarbamoilowy, w którym rodniki alkilowe maja od 1 do 4 atomów wegla, grupa alkilotio, alkilosulfinylowa, alkilosulfonylowa, kazda majaca od 1 do 4 atomów wegla, grupa alkilokarbonyloksylowa, o 2-5 atomach wegla, grupa alkilokarbonylo- aminowa o 2—5 atomach wegla lub grupa cyjanowa.2 136683 Zwiazki o wzorze 1 mozna wytworzyc znanymi sposobami poprzez reakcje w temperaturze pomiedzy 2 i 140°C posredniego chlorku kwasowego o wzorze 2 (w którym X oznacza chlor, brom lub jod a A, B, C, D, E i 7 maja znaczenie powyzej podane) z sulfonamidem o wzorze R3 S02 NH2, w którym R3 ma wyzej podane znacz - nie, w obecnosci akceptora kwasu zwlaszcza aminy trzeciorzedowej takiej jak N,N-dwumetyloanilina lub pirydyj na albo weglanu metalu alkalicznego na przyklad bezwodnego weglanu potasowego albo fluorku metalu alkalic/f nego na przyklad fluorkucezu. ? Zwiazki o wzorze 1, w którym R4 jest atomem wodoru, mozna alkilowac znanym sposobem na przyklat poprzez reakcje z dwuazoalkanem o 1-4 atomach wegla tak zeby otrzymac odpowiednie produkty w którycj R4 jest rodnikiem alkilowym o 1 -4 atomachwegla. / Ten sposób kondensacji zwiazków o wzorze 2 i R3 S02NH2 m& liczne niedogodnosci a mianowicie wydajnos¬ ci sa srednie (na przyklad mozna obliczyc wydajnosc 27% dla przykladu 14 z europejskiego-opisu patentowego 23392 oraz 9,5% dla przykladu 34). Sadzi sie, ze to obecnosc akceptora kwasu obniza wydajnosc dlatego, ze\ sprzyja ona reakcji podwójnego acylowania. Ponadto uzycie akceptora kwasu czyni trudniejszym i kosztowniej-\ szym wyodrebnienie i oczyszczenie produktów koncowych. Celem wynalazku jest usuniecie tych niedogodnosci.} Sposobem wedlug wynalazku wytwarza sie zwiazki o ogólnym wzorze 3 w którym A oznacza grupe N02, B J oznacza atom chloru, C oznacza atom wodoru, D oznacza grupe CF3, E i F oznaczaja atomy wodoru a R oznacza \ grupe CO-NH-S02-CH3 i sposób ten obejmuje reakcje chlorku kwasowego (korzystnie chlorku, bromku lub ) jodku) o wzorze ogólnym 2, w którym X oznacza atom chloru, bromu lub jodu, A oznacza grupe N02, B \ oznacza atom chloru, C oznacza atom wodoru, D oznacza grupe CF3, E i F oznaczaja atomy wodoru, a R oznacza grupe CO—NH—S02-CH3 z sulfonamidem o wzorze CH3S02NH2 bez akceptora kwasu i w takiej tem¬ peraturze w której kwas chlorowcowodorowy (HC1, HBr, HJ) jest usuwany w postaci gazowej ze srodowiska reakcji w miare jego tworzenia sie ale bez znaczniejszego rozkladu produktu reakcji o wzorze 1.Sposobem wedlug wynalazku mozna otrzyniac pochodne sulfonamidowe kwasów fenoksybenzoesowych ze znacznie wyzszymi wydajnosciami, na przyklad wydajnosciami co najmniej okolo 30% a czesto co najmniej okolo 50% oraz ze znacznie prostszym odzyskiwaniem i oczyszczaniem produktu koncowego niz ma to miejsce w znanych dotad sposobach.Temperatura, w której mozna prowadzic sposób wedlug wynalazku, zalezy zwlaszcza od tego czy jest duzy nadmiar halogenku kwasowego o wzorze 2 lub sulfonamidu o wzorze CH3 S02NH2 lub od tego czy uzywa sie lub nie uzywa rozpuszczalnika majacego wlasciwosci katalityczne.Jesli wiec jest duzy nadmiar halogenku kwasowego o wzorze 2 to znaczy gdy stosunek molowy zwiazku o wzorze 2 do zwiazku o wzorze CH3S02NH2 wynosi od okolo 1,5 do 5 to wtedy halogenek kwasowy o wzo¬ rze 2 moze sluzyc jako rozpuszczalnik podczas reakcji a temperatura reakcji moze byc w zakresie pomiedzy 80 i 200°C lecz bardziej korzystna jest w zakresie pomiedzy 90 i 160°C.Nieprzereagowany halogenek kwasowy o wzorze 2 moze byc odzyskany ze srodowiska reakcji poprzez przemywanie obojetnym rozpuszczalnikiem takim jak weglowodór, zwlaszcza pentan, heksan, heptan, cyklopen- tan, cykloheksan, cykloheptan, benzen, toluen, ksylen, chlorowcoweglowodór zwlaszcza chlorobenzeny, CS2, czterowodorofuran, dioksan i inne.Gdy uzywa sie nadmiaru sulfonamidu to znaczy gdy stosunek molowy zwiazku o wzorze CH3S02NH2 do zwiazku o wzorze 2 wynosi od 1,5 do 5 to wtedy reakcje prowadzi sie przewaznie w temperaturze pomiedzy 90 i 200°C a korzystnie pomiedzy 140 i 160°C. Ogólnie biorac temperatura powinna byc wystarczajaca dla stopie¬ nia srodowiska reakcji. Nadmiar sulfonamidu CH3 S02 NH2 mozna odzyskac ze srodowiska reakcji poprzez prze¬ mywanie woda lub innym rozzpuszczalnikiem obojetnym wobec tegoz odczynnika (CH3 S02 NH2 ).Odczynniki mozna równiez rozpuscic w obojetnym rozzpuszczalniku o temperaturze wrzenia wyzszej od temperatury reakcji (na przyklad w cieklym weglowodorze, chlorowanym lub niechlorowanym takim jak ben¬ zen, toluen, ksylen, mieszaniny ksylenów, kumen w którym to przypadku najwyzsza temperatura reakcji korzyst¬ nie jest nieco nizsza od temperatury wrzenia rozpuszczalnika. Tik wiec w przypadku kumenu wrzacego w tem¬ peraturze okolo 153°C reakcje prowadzi sie korzystnie w temperaturze pomiedzy 130 i 150°C. Uzycie obojetne¬ go rozpuszczalnika ma te praktyczna zalete, ze umozliwia lepsze przenoszenie ciepla w sposobie na skale prze¬ myslowa a takze pozwala na unikniecie miejscowego przegrzewania srodowiska reakcji .Wedlug innego wariantu wynalazku stosuje sie rozpuszczalnik o dzialaniu katalitycznym wzgledem reakcji pomiedzy halogenkiem kwasowym o wzorze 2 i sulfonamidem o wzorze CH3S02NH2 dostarczajacej fenoksy- benzoilosulfonamid o wzorze 3. Szczególnie korzystny pod tym wzgledem jest dwumetyloformamid (DMF wrzacy w temperaturze okolo 154°C) oraz dwumetyloacetamid (DMAC wrzacy w temperaturze okolo 164°C) a ich uzycie pozwala na zastosowanie dosc niskiej temperatury, na przyklad pomiedzy 80 i 120°C, korzystnie pomiedzy 90 i 110°C lub wreszcie temperatur podwyzszonych nieco, nizszych od temperatur wrzenia tychze rozpuszczalników. Wieksza jest wtedy szybkosc reakcji. Ponizsze przyklady objasniaja wynalazek i pokazuja jak moze on byc zastosowany.136683 3 Przyklad I. 2 g (0,021 mola) metanosulfonamidu miesza sie z 3,8 g (0,01 mola) chlorku kwasu 5-/2'- -chloro-4'-trójfluorometylo/-fenoksy-2-nitrobenzoesowegOc Mieszanine ogrzewa sie w ciagu 20 minut w temperatu¬ rze 150°C. Ze srodowiska reakcji wydziela sie kwas chlorowodorowy w miare jego tworzenia sie. Nastepnie ochladza sie i otrzymuje czarny olej, który rozpuszcza sie w wodnym roztworze weglanu sodowego. Po prze¬ saczeniu przesacz zakwasza sie rozcienczonym HC1, który wytraca produkt o wzorze 3. W ten sposób z wydaj¬ noscia 71% otrzymuje sie 3,1 g produktu topiacego sie w temperaturze 195— 197°C i majacego pasmo absorp¬ cji w podczerwieni wl69cm'1(grupa 00 ). Produkt ten ma wzór 3.Przyklad II. Postepuje sie jak w przykladzie I lecz stosuje sie 250g chlorku kwasowego i 130g metanosulfonamidu. Produkt reakcji wyodrebnia sie bezposrednio po ochlodzeniu mieszaniny poprzez przekrys- talizowanie z izopropanolu. Uzyskuje sie 185 g produktu o wzorze 3 z wydajnoscia 64%. Budowe tegoz produktu potwierdza widmo w podczerwieni (pasmo absorpcji w 1692 cm"1) oraz magnetyczny rezonans jadrowy (singlet w 3,5 ppm; multiplet w 8,07 ppm).W przypadku zastosowania sposobu z przykladu z europejskiego opisu patentowego 23392 i uzycia pirydyny jako akceptora kwasu wydajnosc wynosila tylko 25%.Zastrzezenia patentowe 1. Sposób wytwarzania pochodnych kwasu fenoksybenzoesowego o ogólnym wzorze 3 polegajacy na reakcji halogenku kwasowego o ogólnym wzorze 2, w którym X oznacza atom chloru, bromu lub jodu, A oznacza grupe N02, B oznacza atom chloru, C oznacza atom wodoru, D oznacza grupe CF3, E i F oznaczaja atomy wodoru, a R oznacza grupe CO-NH-SO2--CH3 z sulfonamidem o wzorze CH3S02NH2 wobec akceptora kwasu, zna¬ mienny tym, ze reakcje prowadzi sie pomiedzy samymi substratami zwiazkiem o wzorze 2 i sulfonamidem i w takiej temperaturze, w której bedacy produktem ubocznym gazowy kwas beztlenowy jest usuwany ze srodo¬ wiska reakcji w miare jego tworzenia sie przy czym temperatura ta jest nizsza od temperatury rozkladu produktu o wzorze 1. 2. Sposób wedlug zastrz. 1,znamienny tym, ze reakcje prowadzi sie w obecnosci nadmiaru halogen¬ ku kwasowego o wzorze 2. 3. Sposób wedlug zastrz. 2, znamienny tym, ze stosunek molowy halogenku kwasowego o wzorze 2 do sulfonamidu o wzorze CH3 S02NH2 wynosi 1,5 do 5. 4. Sposób wedlug zastrz. 2 lub 3, z n a m i e n n y t y m, ze temperatura reakcji wynosi od 80 do 200°C a korzystnie od 90 do 160°C. 5. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w obecnosci nadmiaru sul¬ fonamidu. 6. Sposób wedlug zastrz. 5, znamienny tym, ze stosunek molowy sulfonamidu o wzorze CH3 S02 NH2 do halogenku kwasowego o wzorze 2 wynosi od 1,5 do 5. 7. Sposób wedlug zastrz. 5 lub 6, znamienny t y m, ze temperatura reakcji wynosi od 90 do 200°C a korzystnie od 140 do 160°C. 8. Sposób wedlug zastrz. 1,znamienny tym, ze reakcje prowadzi sie w obecnosci rozpuszczalnika o temperaturze wrzenia wyzszej od temperatury reakcji. 9. Sposób wedlug zastrz. 8, znamienny tym, ze jako rozpuszczalnik stosuje sie weglowodór. 10. Sposób wedlug zastrz. 9, znamienny tym, ze jako rozpuszczalnik stosuje sie kumen a tempera¬ tura wynosi od 130 do 150°C. 11. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w obecnosci rozpuszczalnika o wlasciwosciach katalizujacych reakqe. 12. Sposób wedlug zastrz. 11, znamienny tym, ze jako rozpuszczalnik stosuje sie dwumetylofor- mamid lub dwumetyloacetamid a temperatura wynosi od 80°C do temperatury wrzenia rozpuszczalnika. 13. Sposób wedlug zastrz. 12, znamienny tym, ze utrzymuje sie temperature wyzsza od 90°C. 14.- Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie miedzy zwiazkiem o wzorze 4 i zwiazkiem o wzorze CH3 S02 NH2.WZÓR 1 C B COX D-wV O "^)-A E F WZÓR 2 Cl CO-NH-S02-CH3 WZÓR 3 Cl CO-Cl WZÓR 4 Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 130 zl PL PL PL PL PL

Claims (13)

1. Zastrzezenia patentowe 1. Sposób wytwarzania pochodnych kwasu fenoksybenzoesowego o ogólnym wzorze 3 polegajacy na reakcji halogenku kwasowego o ogólnym wzorze 2, w którym X oznacza atom chloru, bromu lub jodu, A oznacza grupe N02, B oznacza atom chloru, C oznacza atom wodoru, D oznacza grupe CF3, E i F oznaczaja atomy wodoru, a R oznacza grupe CO-NH-SO2--CH3 z sulfonamidem o wzorze CH3S02NH2 wobec akceptora kwasu, zna¬ mienny tym, ze reakcje prowadzi sie pomiedzy samymi substratami zwiazkiem o wzorze 2 i sulfonamidem i w takiej temperaturze, w której bedacy produktem ubocznym gazowy kwas beztlenowy jest usuwany ze srodo¬ wiska reakcji w miare jego tworzenia sie przy czym temperatura ta jest nizsza od temperatury rozkladu produktu o wzorze 1.
2. Sposób wedlug zastrz. 1,znamienny tym, ze reakcje prowadzi sie w obecnosci nadmiaru halogen¬ ku kwasowego o wzorze3. Sposób wedlug zastrz. 2, znamienny tym, ze stosunek molowy halogenku kwasowego o wzorze 2 do sulfonamidu o wzorze CH
3.S02NH2 wynosi 1,5 do 5.
4. Sposób wedlug zastrz. 2 lub 3, z n a m i e n n y t y m, ze temperatura reakcji wynosi od 80 do 200°C a korzystnie od 90 do 160°C.
5. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w obecnosci nadmiaru sul¬ fonamidu.
6. Sposób wedlug zastrz. 5, znamienny tym, ze stosunek molowy sulfonamidu o wzorze CH3 S02 NH2 do halogenku kwasowego o wzorze 2 wynosi od 1,5 do 5.
7. Sposób wedlug zastrz. 5 lub 6, znamienny t y m, ze temperatura reakcji wynosi od 90 do 200°C a korzystnie od 140 do 160°C.
8. Sposób wedlug zastrz. 1,znamienny tym, ze reakcje prowadzi sie w obecnosci rozpuszczalnika o temperaturze wrzenia wyzszej od temperatury reakcji.
9. Sposób wedlug zastrz. 8, znamienny tym, ze jako rozpuszczalnik stosuje sie weglowodór.
10. Sposób wedlug zastrz. 9, znamienny tym, ze jako rozpuszczalnik stosuje sie kumen a tempera¬ tura wynosi od 130 do 150°C.
11. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w obecnosci rozpuszczalnika o wlasciwosciach katalizujacych reakqe.
12. Sposób wedlug zastrz. 11, znamienny tym, ze jako rozpuszczalnik stosuje sie dwumetylofor- mamid lub dwumetyloacetamid a temperatura wynosi od 80°C do temperatury wrzenia rozpuszczalnika.
13. Sposób wedlug zastrz. 12, znamienny tym, ze utrzymuje sie temperature wyzsza od 90°C.14.- Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie miedzy zwiazkiem o wzorze 4 i zwiazkiem o wzorze CH3 S02 NH2.WZÓR 1 C B COX D-wV O "^)-A E F WZÓR 2 Cl CO-NH-S02-CH3 WZÓR 3 Cl CO-Cl WZÓR 4 Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 130 zl PL PL PL PL PL
PL1982237639A 1981-07-27 1982-07-23 Method of obtaining derivatives of phenoxybenzoic acid PL136683B1 (en)

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JPH0149262B2 (pl) 1989-10-24
AT385985B (de) 1988-06-10
IE821786L (en) 1983-01-27
NL8202994A (nl) 1983-02-16
IT1198399B (it) 1988-12-21
IL66197A (en) 1985-11-29
DD203716A5 (de) 1983-11-02
RO85388A (ro) 1984-11-25
PT75322A (fr) 1982-08-01
RO85388B (ro) 1984-11-30
IL66197A0 (en) 1982-11-30
GB2103611A (en) 1983-02-23
GB2103611B (en) 1985-04-03
ES514352A0 (es) 1983-05-01
ATA290082A (de) 1987-11-15
IT8222545A0 (it) 1982-07-23
CA1194472A (en) 1985-10-01
BE893940A (fr) 1983-01-26
IT8222545A1 (it) 1984-01-23
FR2510105A1 (fr) 1983-01-28
BR8204357A (pt) 1983-07-19
IE53978B1 (en) 1989-05-10
FR2510105B1 (pl) 1984-09-07
HU191186B (en) 1987-01-28
LU84295A1 (fr) 1984-03-22
CH652384A5 (fr) 1985-11-15
KR840000466A (ko) 1984-02-22
KR880002591B1 (ko) 1988-12-03
PT75322B (fr) 1985-11-29
JPS5826860A (ja) 1983-02-17
DK333282A (da) 1983-01-28
ES8306108A1 (es) 1983-05-01
PL237639A1 (en) 1983-05-23
SU1215620A3 (ru) 1986-02-28
DE3227847A1 (de) 1983-02-10

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