SE449359B - (s) alfa-cyan-3-fenoxibensyl-2,2-dimetyl-3r-(2,2-diklorovinyl)-cyklopropan-1r-karboxylat och dess anvendning i insektsdodande kompositioner - Google Patents

(s) alfa-cyan-3-fenoxibensyl-2,2-dimetyl-3r-(2,2-diklorovinyl)-cyklopropan-1r-karboxylat och dess anvendning i insektsdodande kompositioner

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Publication number
SE449359B
SE449359B SE8204715A SE8204715A SE449359B SE 449359 B SE449359 B SE 449359B SE 8204715 A SE8204715 A SE 8204715A SE 8204715 A SE8204715 A SE 8204715A SE 449359 B SE449359 B SE 449359B
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phenoxybenzyl
dimethyl
carboxylate
dichlorovinyl
compositions
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SE8204715A
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SE8204715D0 (sv
SE8204715L (sv
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Julien Warnant
Jacques Prost-Marechal
Philippe Cosquer
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Roussel Uclaf
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • 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
    • C07D213/63—One oxygen atom
    • 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
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/18—Oxygen or sulfur atoms

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  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
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  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)

Description

449 559 2 H3C CÛZ H30 H H "- / \ c1 cl och en alkohol (B), optiskt aktiv med strukturen (R) eller ra- cemisk med strukturen (R, S), med den generella formeln B: -/\ HO - C CN “" (R) eller (R, S) eller en blandning i icke ekvimolekylära mängder av en ester av en optiskt_aktiv cyklopropankarboxylsyra (A) och en optiskt aktiv alkohol (B) med strukturen (R) och en ester av en op- tiskt aktiv cyklopropankarboxylsyra (A) och en optiskt aktiv alkohol (B) med strukturen (S), vilken blandning betecknas "ester (R + S)", till en ester av en optiskt aktiv cyklopropan karboxylsyra (A) och en optiskt aktiv alkohol (B) med struktu- ren (S), kännetecknat av att estern av den optiskt aktiva cyk- lopropankarboxylsyran (A) och alkoholen (B), optiskt aktiv med strukturen (R) eller racemisk med strukturen (R, S), eller es- terblandningen betecknad "ester (R + S)", utsättes för inverkan av ett basiskt medel, som utgöres av ammoniak, primära aminer, sekundära aminer, tertiära aminer, kvaternära ammoniumförening- ar, basiska jonbytarhartser, flytande aminer med hög molekylvikt och starka baser, vilka senare användes i katalytiska mängder, i ett lösningsmedel eller en blandning av lösningsmedel, vari estern av den optiskt aktiva cyklopropankarboxylsyran (A) och alkoholen (B) med strukturen (S) är olöslig och estern av den optiskt aktiva cyklopropankarboxylsyran (A) och alkoholen (R) med strukturen (R) är löslig, varefter estern av den optiskt ak- tiva cyklopropankarboxylsyran (A) och alkoholen (B) med struk- turen (S), som sålunda gjorts olöslig, separeras från reaktions- mediet. 449 359 Detta förfarande beskrives i den svenska patentskriften 446 629 och för närmare detaljer hänvisas till denna.
Försök utförda i experimentellt syfte visar en insektsdödande verkan av denna förening gentemot både husflugan och larver av Spodoptera littoralis.
(S) a-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2-diklorvinyl)-cyk- lopropan-1R-karboxylat kan användas för framställning av insekts- dödande kompositioner, vilka som aktiv beståndsdel kan innehål- la en eller flera av dessa föreningar.
I kompositionerna kan daraktiva substansen ingå som huvudsakligen det enda, men även i kombination med flera andra bekämpningsme- del. Kompositionerna kan ha formen av pulver, granulat, suspen- sioner, emulsioner, lösningar, aerosollösningar, brännbara rem- sor, lockremsor eller andra för detta slag av föreningar vanliga preparat. " Förutom den aktiva beståndsdelen innehåller kompositionerna van- 'ligen en bärare och/eller ett icke joniskt ytaktivt medel, som bland annat tillförsäkrar en jämn dispersion av de i blandningen ingående substanserna. Bäraren kan vara en vätska, såsom vatten, alkohol, kolväten eller andra organiska lösningsmedel, mineral- olja, animalisk eller vegetabilisk olja, ett pulver såsom t.ex. talk, lera, silikater, kiselgur, eller ett fast brännbart ämne.
För att öka föreningens insekticida verkan kan man tillsätta de inom ifrågavarande användningsområde vanliga synergistiska med- len, såsom t.ex. J-(2,5,8-trioxadodekyl-2-propyl-4,§-metylendi- oxi)bensen (eller piperonylbutoxid)q N-(2-etylheptyl)bicyklo- -[2,2,17-5-hepten-2,3-dikarboximid, piperonyl-bis-21(2'-n-but- oxietoxi)-etylacetal (eller tropital). ' De insekticida kompositionerna innehåller företrädesvis mellan 0,005 och 1,0 vikta aktiv förening.
Följande exempel belyser uppfinningen utan att begränsa densam- ma. 449 359 Exempel 1 Omvandling av a-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2-dikloro- vinyl)-cyklopropan-1R-karboxylat från (R)-form till (S)-form a) Framställning av alkoholestern med strukturen (R) g raeemisk (R, s)-eikeheieeter, /&]â° = +16ys° (e = 10%, ben- sen) kromatograferades på kiselsyragel med ett elueringsmedel be- stående av en blandning av petroleumeter (kokp. 40-70°C) och iso- É propyleter (85/15), varvid erhölls 3 g (R) u-cyan-3-fenoxibensyl- -2,2-dimetyl-3R-(2,2-diklorovinyl)-cyklopropan-1R-karboxylat, LÄIÉO = -310 (c = 1%, bensen) eller Åšjšo = -21,5° (c = 1%, klo- roform). b) Omvandling till alkoholester med strukturen (S) f Till 60 q (R) u-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2-dikloro- vinyl)-cyklopropan-1R-karboxylat, [å šo = -310 (c = 1%, bensen) eller [Q]š0 = -21,50 (c = 1%, kloroform) framställt enligt para- graf a), sattes 120 cm3 isopropanol och därefter 9 cm3 vattenlös- ning av ammoniak, 22°Bë, varpå blandningen kyldes till OOC och omrördes under 48 timmar vid OOC. Produkten isolerades genom att _den bildade fällningen fick lufttorka, tvättades med 30 cm3 iso- propanol vid -2o°c och torkedee. men erhöll 48,5 g (s) aieyen-3- -fenoxibensyl-2,2-dimetyl-3R-(2,2-diklorovinyl)-cyklopropan-1R- -karboxylat. _ I smaitpunkt 6o°c, ¿ä7š° = +66° (e =_1%, bensen) eller ¿Q7š° = +34° (c = kloroform).
Exémgel 2 I Omvandling av u-cyan-3-fenoxibensyl-2,2-dimetyl-3R)-(2,2-dikloro- vinyl)-cyklopropan-IR-karboxylat från (R,S)-form till (S)-form Till soc g racemiek (R,s)-elkeneleeter, ¿Q]š0 = +1s,s° (e = 1%, bensen), sattes 1200 cm3 isopropanol,uvarefter man till den er- 7 hållna lösningen satte 90 cm3 vattenlösning av ammoniak, 22°Bê, - kylde den till OOC och omrörde densamma under 48 timmar vid den- I na temperatur. Produkten isolerades genom att den bildade fällnin- gen fick lufttorka, tvättades med 300 cm3 isopropanol vid_-20qC och torkades. Man erhöll 485 g (S) a-cyan-3-fenoxibensyl-2,2-di- metyl-3R-(2,2-diklorovinyl)-cyklopropan-1R-karboxylatr 449 359 SmältPUnkï 60°C| Äšyšo = +66° (C = 1%, bensen) eller Ãë7â0 = +34° (c = 1%, kloroform).
Analys för C N 0 NCl3 (416,28) 22 19 3 Beräknat: C 63,48% H 4,60% N 3,36% Cl 17,03% Funnet: C 63,7% H 4,6% N 3,4% Cl 17,1% Exempel 3 Komposition baserad på (S) a-cyan-3-fenoxibensyl-2,2-dimetyl-3R- '-(2,2-diklorovinyl)-cyklopropan-1R-karboxylat Man blandade: (S) u-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2-diklorovinyl)-cyk- lopropan-1R-karboxylat 25 g/1 2,6-di-tert.-b tylparakresol _ 10 g/1 Emcol H 300 B(š>*) 50 g/1 Emcoi H 5 o B *) 20 9/1) Supersol **) 786 g/1 *) Dessa ytaktiva medel är blandningar av kalciumsalter av al- kylbensensulfonater (anjonisk del) och polyoxietenetrar (icke jonisk del), vilka försäljes av firma Wite.
**) Supersol är en blandning av aromatiska lösningsmedel, vilken försäljes av firma B.P. (Shell). Å Undersökning av den insekticida effekten av (S) a-c§an-3-fenoxi- bensyl-2,2-dimetyl-3R-(2,2-diklorovinyl)-cyklopropan-1R-karb- oxylat (förening A) a) Undersökning av insekticid inverkan på husflugan De testade insekterna var husflugor av båda könen. Man anbringa- de topiskt 1 pl acetonlösning på insektens rygg. Varje behand- ling innefattade 50 flugor. Mortaliteten registrerades 24 timmar efter behandlingen och den letala dosen 50 av föreningen_bestäm- des. ,_ , De vid experimenten erhållna resultaten sammanfattas i nedanstå- ende tabell. 449 359 6 Dosering Mortalitet efter 24 h, % LD50 93,3 3,75 83,2 2,5 68,0 1,6 nanogram 1,25 34,5 per insekt f 0,625 10,0 (SJ Slutsats: Förening A har en mycket kraftig insekticid inverkan på husflu- gan. b) Undersökning av insekticid inverkan på larver av Spodoptera littoralis Försöken utfördes genom topisk applicering. Man anbringade 1 pl acetonlösning av föreningen på ryggen av varje insekt. Varje dos gavs till 15 larver av Spodoptera littoralis i 4:e larvstadiet.
Efter behandlingen placerades larverna i en artificiell närande miljö (miljö enligt Poitot). Effekten (procentuell mortalitet räknat på icke behandlade kontrolldjur) 24 och 48 timmar efter behandlingen registrerades, och den letala dosen 50 (LD50) av för~ eningen i nanogram per larv bestämdes.
De vid experimenten erhållna resultaten sammanfattas i nedanstå- ende tabell.
Mortalitet i % efter LD50 efter Dosering 24 h 48 h 48 h 1,25 85,6 97,8 0,625 80,0 82,2 0,3 nanogram 0,3125 48,9 62,2 per larv 0,1562 20,5 27,3

Claims (2)

449 359 Patentkrav
1. (S) a-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2-diklorovi- nyl)-cyklopropan-1R-karboxylat till användning som insektsdö- dande medel.
2. Användning av (S) u-cyan-3-fenoxibensyl-2,2-dimetyl-3R-(2,2- diklorovinyl)-cyklopropan-1R-karboxylat enligt krav 1 såsom ak- tiv huvudbeståndsdel i insektsdödande kompositioner.
SE8204715A 1976-04-23 1982-08-16 (s) alfa-cyan-3-fenoxibensyl-2,2-dimetyl-3r-(2,2-diklorovinyl)-cyklopropan-1r-karboxylat och dess anvendning i insektsdodande kompositioner SE449359B (sv)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7612094A FR2375161A1 (fr) 1976-04-23 1976-04-23 Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)

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SE8204715D0 SE8204715D0 (sv) 1982-08-16
SE8204715L SE8204715L (sv) 1982-08-16
SE449359B true SE449359B (sv) 1987-04-27

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SE7704518A SE446629B (sv) 1976-04-23 1977-04-20 Sett att omvandla en optiskt aktiv ester av en kiralsyra och en sekunder alfa-cyanalkohol med strukturen (r) till en ester av en kiralsyra och en sekunder alfa-cyanalkohol med strukturen (s)
SE8204715A SE449359B (sv) 1976-04-23 1982-08-16 (s) alfa-cyan-3-fenoxibensyl-2,2-dimetyl-3r-(2,2-diklorovinyl)-cyklopropan-1r-karboxylat och dess anvendning i insektsdodande kompositioner

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SE7704518A SE446629B (sv) 1976-04-23 1977-04-20 Sett att omvandla en optiskt aktiv ester av en kiralsyra och en sekunder alfa-cyanalkohol med strukturen (r) till en ester av en kiralsyra och en sekunder alfa-cyanalkohol med strukturen (s)

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Publication number Priority date Publication date Assignee Title
DE2326077C2 (de) * 1972-05-25 1985-12-12 National Research Development Corp., London Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide
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CH635563A5 (fr) * 1977-07-07 1983-04-15 Sumitomo Chemical Co Procede pour la preparation d'un alpha-cyano-3-phenoxybenzyle optiquement actif.
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LU77183A1 (sv) 1977-11-22
JPS612642B2 (sv) 1986-01-27
DK171573B1 (da) 1997-01-20
SU990082A3 (ru) 1983-01-15
IL51958A (en) 1983-02-23
CH620889A5 (sv) 1980-12-31
MY8500509A (en) 1985-12-31
DE2718039A1 (de) 1977-11-17
SE8204715D0 (sv) 1982-08-16
YU104777A (en) 1983-04-30
HK51884A (en) 1984-06-22
NO149104C (no) 1984-02-15
CA1130311A (fr) 1982-08-24
PT66468A (fr) 1977-05-01
NZ183938A (en) 1979-10-25
FR2375161A1 (fr) 1978-07-21
DD130929A5 (de) 1978-05-17
DK177077A (da) 1977-10-24
BE853867A (fr) 1977-10-24
NO771244L (no) 1977-10-25
GR63104B (en) 1979-09-05
IE45496B1 (en) 1982-09-08
HK51984A (en) 1984-06-22
YU40297B (en) 1985-12-31
HRP931394B1 (en) 1996-04-30
DK170732B1 (da) 1995-12-27
SE446629B (sv) 1986-09-29
PT66468B (fr) 1979-03-09
NO149104B (no) 1983-11-07
AR228557A1 (es) 1983-03-30
PL113207B1 (en) 1980-11-29
NL7704521A (nl) 1977-10-25
HU181942B (en) 1983-11-28
ATA289677A (de) 1980-07-15
CS214851B2 (en) 1982-06-25
AT364675B (de) 1981-11-10
PL117200B1 (en) 1981-07-31
US4133826A (en) 1979-01-09
ES458112A1 (es) 1978-03-16
AT360970B (de) 1981-02-10
ZA772474B (en) 1978-06-28
ATA929178A (de) 1981-04-15
FR2375161B1 (sv) 1979-04-13
DK317589D0 (da) 1989-06-27
IE45496L (en) 1977-10-23
US4136195A (en) 1979-01-23
OA05636A (fr) 1981-04-30
TR19049A (tr) 1978-04-12
JPS6127385B2 (sv) 1986-06-25
NL180934C (nl) 1987-05-18
AU512155B2 (en) 1980-09-25
NL180934B (nl) 1986-12-16
GB1582596A (en) 1981-01-14
BR7702576A (pt) 1977-11-29
DK317589A (da) 1989-06-27
AU2459577A (en) 1978-11-02
DE2718039C2 (de) 1985-02-28
JPS52148040A (en) 1977-12-08
IT1073208B (it) 1985-04-13
SE7704518L (sv) 1977-10-24
SE8204715L (sv) 1982-08-16
GB1582595A (en) 1981-01-14
PL197553A1 (pl) 1978-01-02
SG23184G (en) 1985-01-04
MX5299E (es) 1983-06-13
JPS52131559A (en) 1977-11-04
SG23284G (en) 1985-01-04

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