PL142913B1 - Method of obtaining novel derivatives of gydroxylamine - Google Patents

Method of obtaining novel derivatives of gydroxylamine Download PDF

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Publication number
PL142913B1
PL142913B1 PL1984253011A PL25301184A PL142913B1 PL 142913 B1 PL142913 B1 PL 142913B1 PL 1984253011 A PL1984253011 A PL 1984253011A PL 25301184 A PL25301184 A PL 25301184A PL 142913 B1 PL142913 B1 PL 142913B1
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radical
formula
scheme
carbon atoms
compound
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PL1984253011A
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PL253011A1 (en
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Roussel Uclaf
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
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    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Indole Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
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  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
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Description

Przedmiotem wynalazku jest sposób wytwarzania nowych pochodnych hydroksyloaminy o wzorze 1,- w którym Ar oznacza rodnik fenyIowy, ewentualnie podstawiony jednym lub kilkoma rodnikami wybranymi z grupy obejmujacej atomy chlorowca, grupy N02 i CM, rodniki o wzorze 2, w którym FL i R? sa takie same lub rózne i oznaczaja atom wodoru lub rodnik alkilowy, prosty lub rozgaleziony o 1-4 atomach wegla, dalej rodniki alkilowe proste lub rozgalezione, na¬ sycone lub nienasycone, zawierajace do 4 atomów wegla, ewentualnie podstawione jednym lub kilkoma atomami chlorowca, dalej rodniki -COR^, w których R^ oznacza rodnik alkilowy, za¬ wierajacy do 4 atomów wegla, dalej rodnik C02Rif, w którym R^ oznacza rodnik alkilowy o 1-4 atomach wegla, oraz soli addycyjnych tych zwiazków z kwasami, pod warunkiem, ze Ar nie ozna¬ cza ani rodnika fenylowego niepodstawionego, ani rodnika fenylowego monopodstawionego rod¬ nikiem metylowym w pozycjach 2, 3 lub 4, rodnikiem nitrowym w pozycjach 2 lub 4, atomem chloru w pozycjach 3 lub 4, atomem bromu w pozycji 4 lub rodnikiem CF^ w pozycji 4, ani rod¬ nika fenylowego dipodstawionego w pozycji 2 rodnikiem nitrowym i w pozycji 4 rodnikiem CF, lub rodnikiem nitrowym albo tez dipodstawionego w pozycjach 2 i 6 rodnikiem nitrowym, ani rodnika fenylowego tripodstawionego rodnikami nitrowymi w pozycjach 2, 4 i 6 lub rodnikami nitrowymi w pozycjach 2 i 4 i rodnikiem CF, w pozycji 6. Jezeli Ar podstawiony jest przez atom chlorowca, korzystnie jest to atom fluoru, chloru lub bromu; Jezeli R1 i F^ oznaczaja rodnik alkilowy, korzystnie jest to rodnik metylowy, etylowy, n-propylowy lub n-butylowy.Jezeli R, lub FL oznaczaja rodnik alkilowy, korzystnie jest to rodnik metylowy, etylowy, n-propylowy, izopropylowy, n-butylowy, izo-butylowy lub tert-butylowy.2 142 913 Jako sole zwiazków o wzorze 1 mozna wymienic sole addycyjne silnych kwasów takich jak kwas chlorowodorowy, bromowodorowy, siarkowy, azotowy lub trifluorooctowy; Najkorzystniej sposobem wedlug wynalazku wytwarza sie zwiazki o wzorze 1, w którym Ar oznacza rodnik fenylowy podstawiony jednym lub kilkoma rodnikami wyzej wymienionymi lub ich sole addycyjne z kwasami; Z tych ostatnich zwiazków mozna wymienic zwiazki o wzorze 1J w których co najmniej jeden z podstawników rodnika fenylowego stanowi rodnik nitrowy oraz zwiazki o wzorze 1, w których co najmniej jednym z podstawników rodnika fenylowego jest atom chloru w pozycji para; Jako korzystne zwiazki wytwarzane sposobem wedlug wynalazku mozna wymienic np; zwiazki, w których Ar oznacza rodnik fenylowy podstawiony w pozycji 2 rodnikiem nitrowym i w pozycji 4 atomem chloru lub w których Ar oznacza rodnik fenylowy podstawiony w pozycji 4 rod¬ nikiem nitrowym i w pozycji 2 rodnikiem alkilowym prostym lub rozgalezionym o 1-4 atomach wegla, zwlaszcza metylowym lub etylowymi Przedmiotem wynalazku jest zwlaszcza wytwarzanie zwiazków z przykladów, a szczegól¬ nie 0-/2-metylo-4-nitrofenylo/-hydroksyloaminy, "0-2/-chloro-4-nitrofenylo/-hydroksyloaminy, 0-/2-nitro-4-chlorofenylo/-hydroksyloaminy, 0-/2,4-dichlorofenylo/-hydroksyloaminy, 0-/4- nitro-2-trifluorometylofenylo/-hydroksyloaminy, 0-/4-cyjanofenylo/-hydroksyloaminy, 0-/3- -/propyn-2-yloksy/-4-nitrofenylo/-hydroksyloaminy, 0-/3,4-dichlorofenylo/-hydroksyloaminy, oraz ich soli addycyjnych z kwasami i Przedmiotem wynalazku jest równiez szczególnie sposób wytwarzania zwiazku o wzo¬ rze 3, w którym z' oznacza atom fluoru, chloru lub bromu, zwiazków o wzorze 4, dalej zwiazków o wzorach 5, 6, 7, 8, 9, 10, 11 i 12; Sposób wedlug wynalazku polega na tym, ze zwiazek o wzorze 13, w którym Ar ma wyzej podane znaczenie poddaje sie dzialaniu zwiazku o wzorze ^NOSO^H, przy czym otrzymuje sie odpowiedni zwiazek o wzorze 1, który ewentualnie poddaje sie reakcji z kwasem w celu wytworzenia soli.Sposób wedlug wynalazku jest przedstawiony na schemacie 1; Zwiazki o wzorze 1 mozna stosowac w rolnictwie jako czynniki wzrostowe roslin, w celu poprawienia stanu fizjologicz¬ nego uprawianych roslin oraz w celu uzyskania wiekszego ciezaru zbiorów; Mozna np. otrzymac wzrost ciezaru zbiorów korzeni, straków, owoców i lisci. Mozna Stosowac zwiazki o wzorze 1 na soje, pszenice, jeczmien, owies, bawelne, fasole, pomidory, cebule, ziemniaki, salaty, rózowate, zlozone (composacees) itp;, a zwlaszcza na rosliny zwane C, (to jest rosliny, których pierwszy produkt tworzony w toku fotosyntezy stanowi czasteczke o trzech atomach wegla); Zwiazki o wzorze 1 zmniejszaja hamowanie fotosyntezy przez tlen.Zwiazki o wzorze 1 stosuje sie jako substancje czynna do wytwarzania srodków uzy¬ wanych jako czynniki wzrostowe roslin; Ebnizsze przyklady ilustruja wynalazek nie ograniczajac jego zakresu.Przyklad I. Chlorowodorek 0-/3-trifluorometylofenylo/-hydroksyloaminy; Ogrzewa sie pod chlodnica zwrotna mieszanine 33,6 g potasu, 100 g 3-trifluorometylofenolu, 420 cnr wody i 200 cnr metylocykloheksanu. Zatrzymuje sie ogrzewanie i wprowadza sie swiezo przygotowany roztwór 17 g kwasu hydroksyloamino-O-sulfonowego w 40 cnr wody. Fb 10 minutach ogrzewania pod chlodnica zwrotna oziebia sie do 20°, dekantuje i ekstrahuje eterem. Laczy sie fazy organiczne, przemywa woda, normalnym roztworem NaOH, woda i suszy sie. Zakwasza sie za pomoca etanolowego roztworu bezwodnego chlorowodoru; Odciska sie utworzony osad, przemywa eterem, suszy pod zmniejszonym cisnieniem i otrzymuje 6 g zadanego produktu o tem¬ peraturze topnienia 160-162°C;142 913 3 Postepujac jak wyzej otrzymano. nast epujace zwiazki o wzorze 1 ze zwiazków wyjscio¬ wych o wzorze 13* Przykl ad II. Chlorowodorek 0-/4-etoksykarbonylofenylo/-hydroksyloaminy• Rstepuje sie zgodnie ze schematem 2i Przykl ad III* Chlorowodorek 0-/4-terbutylofenylo/-hydroksyloaminy, zste¬ puje sie zgodnie ze schematem 3• Przykl ad IV; 0-/2,4-dichlorofenylo/-hydroksyloaminai Postepuje sie zgodnie ze schematem 4i Przyklad Vi Chlorowodorek 0-/4-fluorofenylo/-hydroksyloaminy; Rostepuje sie zgodnie ze schematem 5* Przykl ad Vii 0-/4-dimetylokarbamoilofenylo/-hydroksyloamina. Postepuje sie zgodnie ze schematem 6i 4-hydroksy-N, N-dimetylobenzamid stosowany Jako produkt wyjsciowy wytwarza sie wedlug schematu 7i Przyklad Viii Chlorowodorek 0-/4-9hloro-3-metylofenylo/-hydroksyloaminy; Postepuje sie zgodnie ze schematem 8i Przyklad VIIIi Chlorowodorek 0-/4-chloro-2-metylofenylo/-hydroksyloaminyi Postepuje sie zgodnie ze schematem 9i Przyklad IXi 0-/4-cyjanofenylo/-hydroksyloaminy. Postepuje sie zgodnie ze schematem 10.Przyklad Xi Chlorowodorek 0-/3-chlorofenylo/-hydroksyloaminy. Fbstepuje sie zgodnie ze schematem 11 i Przyklad Xli 0-/3-nitrofenylo/ -hydroksyloamina. Postepuje sie zgodnie ze schematem 12# Przyklad Xlii 0-/4-acetylofenylo/-hydroksyle amina i Postepuje sie zgodnie ze schematem 13* Przyklad Xliii Chlorowodorek 0/3,4-dichlorofenylo/-hydroksyloaminyi Poste¬ puje sie zgodnie ze schemateml4i ' ' Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych hydroksyloaminy o wzorze 1, w którym Ar oznacza rodnik fenylowy ewentualnie podstawiony jednym lub kilkoma rodnikami wybranymi z grupy obejmujacej, atomy chlorowcaf grupy NCL i CN, rodniki o wzorze 2, w którym R, i FU sa takie same lub rózne i oznaczaja atom wodoru lub rodnik alkilowy, prosty lub rozgale¬ ziony o 1-4 atomach wegla, dalej rodniki alkilowe, proste lub rozgalezione, nasycone lub nienasycone, zawierajace do 4 atomów wegla, ewentualnie podstawione jednym lub kilkoma atomami chlorowcat dalej rodniki -COR,, w których FU oznacza rodnik alkilowy, zawierajacy do 4 atomów wegla, dalej rodnik CÓ2R.A, w którym R^ oznacza rodnik alkilowy o 1-4 atomach wegla oraz soli addycyjnych tych zwiazków z kwasami pod warunkiem, ze Ar nie oznacza ani rodnika fenylowego niepodstawionego, ani rodnika fenylowego monopodstawionego rodnikiem metylowym w pozycjach 2, 3 lub 4, rodnikiem nitrowym w pozycjach 2 lub 4, atomem chloru w pozycjach 3 lub 4, atomem bromu w pozycji 4 lub rodnikiem CF^ w pozycji 4, ani rodnika fenylowego dipodstawionego w pozycji 2 rodnikiem nitrowym i w pozycji 4 rodnikiem CF, lub rodnikiem nitrowym albo tez dipodstawionego w pozycjach 2 i 6 rodnikiem nitrowym, ani rodnika fenylowego tripodstawionego rodnikami nitrowymi w pozycjach 2, 4 i 6 albo rodnikami nitrowymi w pozycjach 2 i 4 i rodnikiem CF^ w pozycji 6, znamienny tym, ze zwiazek o wzorze 13, w którym Ar ma wyzej podane znaczenie, poddaje sie reakcji ze zwiazkiem o wzorze t^NOSCUH, a nastepnie otrzymany zwiazek o .wzorze 1, ewentualnie przeprowadza sie w sól na drodze reakcji z kwasem.4 142 913 2# Sposób wedlug zastrz* 1f znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik fenyIowy podstawiony co najmniej przez atom chloru w pozycji para* 3# Sposób wedlug zastrz* 1, znamienny tym, ze jako zwiazek wyjsciowy . stosuje sie zwiazek o wzorze 13* w którym Ar oznacza rodnik fenylowy podstawiony w pozycji 2 rodnikiem nitrowym i w pozycji 4 atomem chloru. 4. Sposób wedlug zastrz, 1, znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik fenylowy podstawiony w pozycji 4 rodnikiem nitrowym i w pozycji 2 rodnikiem alkilowym, prostym lub rozgalezionym o 1-4 atomach wegla* 5« Sposób wedlug zastrz. 1, znamienny tym, ze jako zwiazek wyj sciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik 2-metylo-4-nitrofenylowy, 6. Sposób wedlug zastrz. 1, znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik 2-chloro-4-nitrofenylowy, 2-nitro-4-chlorofenylowy, 2,4-dichlorofenyIowy, 4-nitro-2-trifluorometylofenylowy, 4-cyja- nofenylowy, 3-/propyn-2-yloksy/-4-nitrofenylowy lub 3,4-dichlorofenylowy.Ar-0-NH2.WZÓR 1 co- ¦A -N R2 °2N-C^-°NH2 CN WZÓR k WZÓR 2 ONH N02 cihOmdnh 2 ^ V^-"Nn2 CH-CHq CL !• 3 WZÓR 3 WZÓR 51W 913 Cl^fONH2 C^° c(V CH3 WZÓR 6 Cl WZÓR 7 2 WZÓR 9 Qhonh2 \_. CN WZÓR 10 CL O^0NH2 O^0NH;2 / CH3 CL WZÓR 8 WZtfR n Cl ci -(oy-oNH2 Cl WZÓR 12142 913 OH H3C—C—CH3 (K ONH< ,HCl H3C-C—CH. tt=U0°C CH.SCHEMAT 3 OH CL Cl ONH2 .CL Cl tt=79v80 C SCHEMAT 4142 913 H?NOSO,H ArOH ^ ? Ar-O-N-H H WZÓR 13 \ SCHEMAT 1 ONH- H2NQS03H r II ,HCl C02C2H5 CC^H 1 tt=135°C SCHEMAT 2na 913 ONH2 ,HCl SCHEMAT 5 tt =144-146 C (rozklfad ) ONH- CH.CON NCH 3 SCHEMAT 6 tt =103-104 C142 913 OCOCH3 OCOCH3 OCOCH3 HO ,CH3 ^ CH3 I C02H C02CL CON. CON CH3 NCH. tt=160-161°C SCHEMAT 7 OH ONH2 , HCL i CH3 CL tt = 15A-156°C SCHEMAT 8142 913 CH- SCHEMAT 9 ONH2 , HCl CL tt=130—132 C ONH- CN tt = 110C SCHEMAT 10na 913 ONH- Cl , HCL tt = 155 C SCHEMAT 11 ONH- NO- NO- tt = 56 C SCHEMAT 12142 913 OH SCHEMAT 13 SCHEMAT U ONH2 COCH3 COCH 3 tt=118°C CL I Cl CL Cl tt = 175°C Pracownia Poligraficzna UP PRL. Naklad 100 egz Cena 220 zl PL PL

Claims (6)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych hydroksyloaminy o wzorze 1, w którym Ar oznacza rodnik fenylowy ewentualnie podstawiony jednym lub kilkoma rodnikami wybranymi z grupy obejmujacej, atomy chlorowcaf grupy NCL i CN, rodniki o wzorze 2, w którym R, i FU sa takie same lub rózne i oznaczaja atom wodoru lub rodnik alkilowy, prosty lub rozgale¬ ziony o 1-4 atomach wegla, dalej rodniki alkilowe, proste lub rozgalezione, nasycone lub nienasycone, zawierajace do 4 atomów wegla, ewentualnie podstawione jednym lub kilkoma atomami chlorowcat dalej rodniki -COR,, w których FU oznacza rodnik alkilowy, zawierajacy do 4 atomów wegla, dalej rodnik CÓ2R.A, w którym R^ oznacza rodnik alkilowy o 1-4 atomach wegla oraz soli addycyjnych tych zwiazków z kwasami pod warunkiem, ze Ar nie oznacza ani rodnika fenylowego niepodstawionego, ani rodnika fenylowego monopodstawionego rodnikiem metylowym w pozycjach 2, 3 lub 4, rodnikiem nitrowym w pozycjach 2 lub 4, atomem chloru w pozycjach 3 lub 4, atomem bromu w pozycji 4 lub rodnikiem CF^ w pozycji 4, ani rodnika fenylowego dipodstawionego w pozycji 2 rodnikiem nitrowym i w pozycji 4 rodnikiem CF, lub rodnikiem nitrowym albo tez dipodstawionego w pozycjach 2 i 6 rodnikiem nitrowym, ani rodnika fenylowego tripodstawionego rodnikami nitrowymi w pozycjach 2, 4 i 6 albo rodnikami nitrowymi w pozycjach 2 i 4 i rodnikiem CF^ w pozycji 6, znamienny tym, ze zwiazek o wzorze 13, w którym Ar ma wyzej podane znaczenie, poddaje sie reakcji ze zwiazkiem o wzorze t^NOSCUH, a nastepnie otrzymany zwiazek o .wzorze 1, ewentualnie przeprowadza sie w sól na drodze reakcji z kwasem.4 142 913
2. # Sposób wedlug zastrz* 1f znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik fenyIowy podstawiony co najmniej przez atom chloru w pozycji para*
3. # Sposób wedlug zastrz* 1, znamienny tym, ze jako zwiazek wyjsciowy . stosuje sie zwiazek o wzorze 13* w którym Ar oznacza rodnik fenylowy podstawiony w pozycji 2 rodnikiem nitrowym i w pozycji 4 atomem chloru.
4. Sposób wedlug zastrz, 1, znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik fenylowy podstawiony w pozycji 4 rodnikiem nitrowym i w pozycji 2 rodnikiem alkilowym, prostym lub rozgalezionym o 1-4 atomach wegla*
5. « Sposób wedlug zastrz. 1, znamienny tym, ze jako zwiazek wyj sciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik 2-metylo-4-nitrofenylowy,
6. Sposób wedlug zastrz. 1, znamienny tym, ze jako zwiazek wyjsciowy stosuje sie zwiazek o wzorze 13, w którym Ar oznacza rodnik 2-chloro-4-nitrofenylowy, 2-nitro-4-chlorofenylowy, 2,4-dichlorofenyIowy, 4-nitro-2-trifluorometylofenylowy, 4-cyja- nofenylowy, 3-/propyn-2-yloksy/-4-nitrofenylowy lub 3,4-dichlorofenylowy. Ar-0-NH2. WZÓR 1 co- ¦A -N R2 °2N-C^-°NH2 CN WZÓR k WZÓR 2 ONH N02 cihOmdnh 2 ^ V^-"Nn2 CH-CHq CL !• 3 WZÓR 3 WZÓR 51W 913 Cl^fONH2 C^° c(V CH3 WZÓR 6 Cl WZÓR 7 2 WZÓR 9 Qhonh2 \_. CN WZÓR 10 CL O^0NH2 O^0NH;2 / CH3 CL WZÓR 8 WZtfR n Cl ci -(oy-oNH2 Cl WZÓR 12142 913 OH H3C—C—CH3 (K ONH< ,HCl H3C-C—CH. tt=U0°C CH. SCHEMAT 3 OH CL Cl ONH2 .CL Cl tt=79v80 C SCHEMAT 4142 913 H?NOSO,H ArOH ^ ? Ar-O-N-H H WZÓR 13 \ SCHEMAT 1 ONH- H2NQS03H r II ,HCl C02C2H5 CC^H 1 tt=135°C SCHEMAT 2na 913 ONH2 ,HCl SCHEMAT 5 tt =144-146 C (rozklfad ) ONH- CH. CON NCH 3 SCHEMAT 6 tt =103-104 C142 913 OCOCH3 OCOCH3 OCOCH3 HO ,CH3 ^ CH3 I C02H C02CL CON. CON CH3 NCH. tt=160-161°C SCHEMAT 7 OH ONH2 , HCL i CH3 CL tt = 15A-156°C SCHEMAT 8142 913 CH- SCHEMAT 9 ONH2 , HCl CL tt=130—132 C ONH- CN tt = 110C SCHEMAT 10na 913 ONH- Cl , HCL tt = 155 C SCHEMAT 11 ONH- NO- NO- tt = 56 C SCHEMAT 12142 913 OH SCHEMAT 13 SCHEMAT U ONH2 COCH3 COCH 3 tt=118°C CL I Cl CL Cl tt = 175°C Pracownia Poligraficzna UP PRL. Naklad 100 egz Cena 220 zl PL PL
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ES8503331A1 (es) 1985-02-16
ES529940A0 (es) 1984-11-01
ZA84967B (en) 1985-03-27
FR2541282A1 (fr) 1984-08-24
EP0119892B1 (fr) 1986-08-13
ES8500958A1 (es) 1984-11-01
MA20040A1 (fr) 1984-10-01
PL142746B1 (en) 1987-11-30
CA1219591A (fr) 1987-03-24
ES533525A0 (es) 1985-02-16
ATE21385T1 (de) 1986-08-15

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