PL129488B1 - Process for preparing novel esters of cyclopropanecarboxylic acids containing multihalogen substituent - Google Patents
Process for preparing novel esters of cyclopropanecarboxylic acids containing multihalogen substituent Download PDFInfo
- Publication number
- PL129488B1 PL129488B1 PL1977214250A PL21425077A PL129488B1 PL 129488 B1 PL129488 B1 PL 129488B1 PL 1977214250 A PL1977214250 A PL 1977214250A PL 21425077 A PL21425077 A PL 21425077A PL 129488 B1 PL129488 B1 PL 129488B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- acid
- radical
- chlorine
- Prior art date
Links
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims 2
- 150000002148 esters Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 150000003254 radicals Chemical group 0.000 claims 9
- -1 alkyl radicals Chemical class 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical class [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000012336 iodinating agent Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (4)
1. Zastrzezenia patentowe 1. Sipoisób wytwarzania nowych esltrów kwasów cykilopropianokarfboki&ylowych zawierajacych wielo- halogemowy podstawnik w ich wiszytertkicih mozli¬ wych odmianach lilzomerycznyicn o wzorze 1, w któryirn Xi oznacza altom wodoru, fluoru, chloru lub bromu, X2 takie sarnio lub rózoe od Xi ozna¬ cza altom fluoru, chloru luib bromu, X3 oznacza arbom chloru, bromu luib jodu zais R oznacza: rod¬ nik benzylowy ewentualnie podstawiony jednym lub wiecej rodnikami takimi jak rodniki alkilowe zawierajace 1 — 4 atomów wegla, rodniki al- kenylowe zawiierajiace 2-^6 atomów wegla., rodniki afUkemyloksyilowie zawierajace 2,—6 atomów wegla, .rodniki alkaldienylowe zawierajace 4M8 atomów wegla, rodnik dwuokisymetylenowy, rodnik benzy- ilowy, altomy chlorowca, albo R oznacza; grupe o wzorze 2, w którym Ri oznacza atom wodoru lub rodnik metylowy, zas R2 oznacza rodnik fenylowy lub grulpe ^OH2—C=GH, a w szczególnosci grupe 5-ibenzylo-3-tfurylo-metylowa, albo R, oznacza gru¬ pe o wzorze 3, w którym R3 oznacza alifatyczny rodnik organiczny, zawiierajacy 2—6 altomów we- glai i jedno lub wiecej polaczen nienasyconych we- 5 giel-wegiel, a w szazegóQnosCl rodnik winylowy, propeni-ll-ylowy, bufra-)ly3-ctienylowy ,lub buten-1- -ylowy, albo R oznacza grupe o wzorze 4, w krtó- rym R4 oznacza atom wodoru, grupe —C=N lub grupe. —C=CH, zas R5 oznacza atom chloru lub 10 rodnik metylowy, przy czym n oznacza, liczbe 0, 1 lub 2, a w szczególnosci grupe 3Hfetnoksybenzyilo- wa, a-cyjano-3^feinoksynbenzylowa lub a-etynylo-3- -fenoksybenzylowa, albo R oznacza, grupe o wzo¬ rze 5, w którym R6, R7, Rs i Rg oznaczaja atom 15 wodoru luib chloru lub rodnik metylowy i w któ¬ rym symbol S/I oznacza pierscien aromatyczny lub analogiczny pierscien diihydronliulb telzra^hyidro-airo- maltyczny, znamienny tym, ze na kwas o ogólnym wzorze 7, w którym Xi i X2 maja wyzej podane 20 zinaiczenie, prlzy czym kwas o wzorze 7 moze miec postac któregokolwiek z jego iizomerów, dziala sie srodkiem chlorujacym, bromujacym lub jodlujacym zdolnym do przylaczania Clg, Ba:2 luib J2 do bocz¬ nego lancucha kwasu o wfcorze 7, po czym otrzy- 25 rnany kwas o ogólnym wzorze 8, w którym Xi, X2 i X3 maija wyzej podane znaczenie ewentualnie przeksztalca isie w jego pochodna funkcyjna, a na¬ stepnie na kwais o wzorze 8 luib jego pochodna funkcyjna dziala sie ailjkoholem R—OH lub jego 30 pochodlna funkcyjna, przy czym R ma wyzej po¬ dane znaczenie.
2. Sposób wedlug zastrz. 1, znamienny tym, ze jako pochodna funkcyjna kwasu o wzorze 8, w którym Xi,,, X2 i X3 maja znaczenie podane w 35 zastrz. 1, sitosiuijie siie chlorek tego kwasu.
3. Sposób wedlug zalstirz. 2, znamienny tym, ze dziala sie chlorkiem kwasu o wzorze 8, w którym Xi, X2 i X3 maja znaczenie podane w zastrz. 1, na alkohol R—OH, prtzy czym R ma znaczienie poda- 40 ne w zaisltrz. 1, w obecnosci zasady trzeciorzedo¬ wej.
4. Sposób wytwarzania nowych estrów kwasów cykloplropanolkairibokisyilowych zawierajacych wielo- halogenowy podsJtawmik w kh wszystkich mozli- 45 wych odmianach izomerycznych o wizorze 1, w którym Xi oznacza aitom wodoru, fluoru, chloru lub bromu, X2 takie samo lub rózne od Xi ozna- cza atom fluoru, chloru luib bromu, X3 oznacza atom chloru, bromu lub jodu, zas R oznacza rodnik 50 benzylowy ewenltualniie podlsitawiony jednym lub wiecej rodnikami takimi jak rodniki alkilowe za¬ wierajace 1—4 atomów wegla, rodniki alkenylowe zawierajace od 2—6 atomów wegla, rodniki alkeny- loksylowe zawierajace 2l-^6 atomów wegla, rodniki 55 ailkaldienylowe zawierajace 4^8 atomów wegla, rod¬ nik dwuokisymetylenowy, rodnik benzylowy, atomy chlorowca, ailbo R oznacza grupe o wzorze 2, w którym Ri ozniaicza atom wodoru lub rodnik mety¬ lowy, zas R2 oznacza rodnik fenylowy luib grupe 60 —OHa—C=OH, a w szczególnosci grulpe 5-benzylo- ^3HfuirylOHmeltylowa, albo R oznacza grupe o wzo¬ rze 3, w którym R3 oznacza alifatyczny rodnik or¬ ganiczny zawierajacy 2—6 atomów wegla i jedno lub wiecej polaczen nienasyconych wegiel-wegiel, 55 a w szczególnosci rodnik wiinylowy, proipen-1-ylo-129 488 49 wy, 'buta-l,3-dienylowy lub buternli-ylowy, albo R oznacza ginu|pe o wzorze 4, w którym R4 oznacza atom wodoru, gruipe -^C=N lufo gru¬ pe —C=CH, zas R5 oznacza atom chloru lulb rod¬ nik metylowy, przy czymn oznacza liczbe 0,1 lulb 2r a w szczególnosci grupe 3^fenoksyfoenzylowa, ^yjaino-3Hfenoklsy-(benizylowa lulb a^etynylo-3-feho- ksybenzylowa, alllbo R oznacza grupe o wzorze 5. w którym R6, R7, Rb i R* oznaczaja aitom wodoru lub chloru lufo rodlnlik metylowy i w którym sym¬ bol S/I oznaczai pierscien aromatyczny lufo analogi¬ czny pieirisoien dliihyidro- lub tetra-.hyidroalromatycz- ny, znamienny tym, ze na pochodna funkcyjna kwasu o ogólnym wzorze 7, w kitótrym Xi i X2 maja wyzej podane znaczeniie, przy czym pochod¬ na funkcyjna kwaisu o wzorze 7 moze miec posiac 10 15 50 któregokolwiek z jego izomerów, dziala sde srod¬ kiem chlorujacym, bromujajcym lufo jodujacym zdol¬ nym do przylaczemia- O2, BtrB lulb J2 do lancucha bocznego pochodnej funkcyjnej kwasu o wzorze 7, po czym na otrzymana pochodna funkcyjna kwa¬ su o wzorze 8, w kitóryim Xi, X2 i X» maija wyzej podane znaczenie, dziada siie alkoholem RH-OH lufo jieigo pochodna funkcyjna, przy czym R mai wy¬ zej /podane znaczeniie. 15. Sposób weidlug zaistrz. 4, znamienny tym, ze jako pochodna funkcyjna kwaisu o wzorze 7 w którym Xi i X2 maija znaczenie podane w zalstrz. 4 i pochodna funkcyjna kwa&u o wzorze 8, w któ¬ rym Xi, X2 i X3 maija znaczenie podane w zastrz. 4, stosuje sie chlorki tych kwasów. —CH2—Fi R1 WZÓR 2 CH2R2 CHj WZCfR 3129 488 H I C— b n WZÓR Rr Rr O "Ts/TTn -ch0- *«^nf R9 O X WZÓR. 5 1 v H H3C CH. 0 CN \ I \ /5 II I c-o-c^/ w h 6^Q WZÓR 6 WZÓR 8 Drukarnia Narodowa, Zaklad Nr 6, 130/86 Cena 100 zl PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7628279A FR2364884A1 (fr) | 1976-09-21 | 1976-09-21 | Nouveaux esters d'acides cyclopropane, carboxyliques comportant un substituant polyhalogene, procedes de preparation et compositions insecticides les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL214250A1 PL214250A1 (pl) | 1980-02-25 |
| PL129488B1 true PL129488B1 (en) | 1984-05-31 |
Family
ID=9177883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977214250A PL129488B1 (en) | 1976-09-21 | 1977-09-20 | Process for preparing novel esters of cyclopropanecarboxylic acids containing multihalogen substituent |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS59152349A (pl) |
| AT (2) | AT353248B (pl) |
| BE (2) | BE858895A (pl) |
| FR (1) | FR2364884A1 (pl) |
| MD (1) | MD222C2 (pl) |
| PL (1) | PL129488B1 (pl) |
| SU (1) | SU858559A3 (pl) |
| TR (1) | TR20005A (pl) |
| ZA (2) | ZA775668B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2380244A1 (fr) * | 1977-02-11 | 1978-09-08 | Ciba Geigy Ag | Composes cyclopropane-carbonyliques utiles a la preparation de composes appropries a la lutte contre les parasites |
| PT67633B (en) * | 1977-02-11 | 1979-07-17 | Ciba Geigy Ag | Process for the preparation of new esters |
| DE2805193A1 (de) * | 1977-02-11 | 1978-08-17 | Ciba Geigy Ag | Cyclopropankarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung |
| FR2432016A2 (fr) * | 1978-07-24 | 1980-02-22 | Roussel Uclaf | Procede de preparation d'esters d'alcools a-cyanes |
| US4277617A (en) * | 1977-10-27 | 1981-07-07 | Roussel Uclaf | Process for the preparation of esters |
| EP0015239A3 (de) * | 1979-02-15 | 1980-09-17 | Ciba-Geigy Ag | Cyclopropankarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| FR2484256B1 (fr) * | 1979-06-29 | 1986-10-24 | Roussel Uclaf | Procede de lutte contre les parasites des animaux a sang chaud |
| OA06730A (fr) * | 1980-01-25 | 1982-06-30 | Roussel Uclaf | Dérivés 3-(buta-1',3'-diényl) substitué de l'acide cyclopropane-1-carboxylique, leur application contre les parasites des végétaux et des animaux à sang chaud, les compositions correspondantes ainsi que les compositions parfumantes les renfermant, leur pré |
| DE3004092A1 (de) * | 1980-02-05 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Substituierte 3-(1,2-dibrom-alkyl)- 2,2-dimethyl-cyclopropan-1-carbonsaeureester, verfahren sowie zwischenprodukte zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
| DE3270859D1 (en) * | 1981-08-31 | 1986-06-05 | Shell Int Research | Protection of crops against soil pests employing an alkylbenzyl cyclopropane carboxylate, novel cyclopropane carboxylates, and compositions containing them |
| JPH0340181U (pl) * | 1989-08-11 | 1991-04-17 | ||
| DE102014107739B4 (de) | 2014-06-02 | 2023-12-07 | Jacques Tchouangueu | Moskitonetz mit Insektenfalle |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1168797A (en) * | 1965-12-09 | 1969-10-29 | Nat Res Dev | Cyclopropane Carboxylic Acid Derivatives and their use as Insecticides |
-
1976
- 1976-09-21 FR FR7628279A patent/FR2364884A1/fr active Granted
-
1977
- 1977-09-15 SU SU772522552A patent/SU858559A3/ru active
- 1977-09-20 BE BE181072A patent/BE858895A/xx not_active IP Right Cessation
- 1977-09-20 BE BE181071A patent/BE858894A/xx not_active IP Right Cessation
- 1977-09-20 PL PL1977214250A patent/PL129488B1/pl unknown
- 1977-09-21 AT AT677277A patent/AT353248B/de not_active IP Right Cessation
- 1977-09-21 ZA ZA00775668A patent/ZA775668B/xx unknown
- 1977-09-21 AT AT677377A patent/AT350043B/de not_active IP Right Cessation
- 1977-09-21 ZA ZA00775669A patent/ZA775669B/xx unknown
-
1980
- 1980-05-16 TR TR20005A patent/TR20005A/xx unknown
-
1983
- 1983-03-02 JP JP58033025A patent/JPS59152349A/ja active Granted
-
1984
- 1984-05-07 JP JP59089573A patent/JPS6011404A/ja active Granted
-
1994
- 1994-09-08 MD MD94-0276A patent/MD222C2/ro not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT350043B (de) | 1979-05-10 |
| MD222B1 (ro) | 1995-06-30 |
| ATA677277A (de) | 1979-04-15 |
| JPS59152349A (ja) | 1984-08-31 |
| AT353248B (de) | 1979-11-12 |
| MD222C2 (ro) | 1995-12-31 |
| ZA775668B (en) | 1978-10-25 |
| FR2364884A1 (fr) | 1978-04-14 |
| TR20005A (tr) | 1980-06-11 |
| ATA677377A (de) | 1978-10-15 |
| JPS64363B2 (pl) | 1989-01-06 |
| PL214250A1 (pl) | 1980-02-25 |
| BE858894A (fr) | 1978-03-20 |
| BE858895A (fr) | 1978-03-20 |
| JPS6011404A (ja) | 1985-01-21 |
| JPS6243985B2 (pl) | 1987-09-17 |
| FR2364884B1 (pl) | 1979-01-12 |
| ZA775669B (en) | 1978-10-25 |
| SU858559A3 (ru) | 1981-08-23 |
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