RU1837763C - Гербицидное средство - Google Patents
Гербицидное средствоInfo
- Publication number
- RU1837763C RU1837763C SU894614351A SU4614351A RU1837763C RU 1837763 C RU1837763 C RU 1837763C SU 894614351 A SU894614351 A SU 894614351A SU 4614351 A SU4614351 A SU 4614351A RU 1837763 C RU1837763 C RU 1837763C
- Authority
- RU
- Russia
- Prior art keywords
- continuation
- herbicide
- chloro
- pyrazole
- hydrogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Изобретение относитс к химическим средствам защиты растений, конкретно, к repi ицидному средству на основе гербицида - сложного пропаргилового эфира 2((5-хлор-3-фторпиридин-2-ил-окси)-фе- нок;и/-пропионовой кислоты и антидота- npo/i заодно го фенил пиразол карбоновой кислоты.
Целью изобретени вл етс уменьшение дистотоксического действи средства на ультурные растени .
Следующие примеры иллюстрируют за- вл0нное средство.
П р и м е р 1. Получение сложного про- паргилового эфира 2(Я)-/4-(5-хлор-3-фтор- пиридин-2-ил-окиси)-фенокси/-пропионо- вой кислоты (гербицид).
К охлаждаемому льдом раствору 4,9 мм (0,035 мол ) триэтиламина и 2 мл (0.035 мол ) пропанола в 40 мл толуола медленно при перемешивании прибавл ют раствор 10,6 г (0,0,30 мол ) хлорида 2(В)-/4н(5-хлор-3-фто- пиридин-2-ил окси)-фенокси/-пропионовой кислоты в 100 мл толуола. Затем реакционную смесь выдерживают перемешива 3 часа при комнатной температуре и выливают в смесь льда с водой, после чего дважды экстрагируют этилацетатом. Экстракт сушат сульфатом магни , фильтруют и выпаривают . Полученный продукт очищают на колонке с силикагелем (элюент - смесь гексана с этилацетатом 2:1). После выпаривани растворител получают кристаллический продукт с температурой плавлени 54°С.
00 СА VI V|
О.
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со
П р и м е р 2. Получение 1-(2-хлорфенил)- З-метоксикарбонил-5-фенилпиразола антидот NJ 1.
К раствору 21,2 г (0,103 мол) метилового эфира бёнзоилпировиноградной кислоты в 100 мл лед ной уксусной кислоты добавл ют 19,3 г (Q.105 мол) гидрохлорида 2-хл орфе- нилгидразина (97%-ного) и 8,6 г (0,105 мол) ацетата натри . После этого реакционную смесь кип т т при температуре кипени флегмы в течение 2 ч, после чего охлаждают ее до комнатной температуры и непосредственно после этого выливают в воду со льдом. Выпавшую при этом смолу внос т в этилацетат и промывают до нейтральной реакции водой и 1м раствором соды, Органическую фазу отдел ют, высушивают над сульфатом натри и испар ют на роторном испарителе. Остывшее масло кристаллизуют из диизопропилового эфира. Таким образом , получают 17,7 г целевого продукта с температурой плавлени 67-70°С. Аналогичным образом получают антидоты , представленные в табл.1.
За вленные средства получают обычными способами, например, смешиванием компонентов.
ПримерЗ. Суспензионный концентрат .
Гербицид и антидот тонко измельчают и смешивают с целевыми добавками в следующем соотношении, мас.%:
аб
активный ингредиент 25 40 этиленгликоль15 . 10
нонилфенилполиэти- ленгликолевый эфир с 15-ю мол ми этилен- оксида10 6 лигнинсульфонат натри 17 10 карбоксиметил целлюлоза1 ,7 1 37%-ный водный раствор формальдегида 0,3 0,2 75%-на водна эмульси силиконового масла 1,5 0,8 вода 29,5 32 Прим ер 4. Эмульсионный концентрат. Тщательно перемешивают ингредиенты в следующем соотношении, мас.%: активный ингредиент25 алкилфенополиэтилен- гликоль с 4-5 мол ми этиленоксида 3 додециобензолсульфонат . кальци 3 простой полигликолевый эфир касторового масла с 35 мол ми этиленоксида 4
циклогексанон20
смесь ксилолов45
Пример 5. В теплице пластиковые горшочки, в которых содержитс 0,5 л зем- ли, засевали семенами ровой пшеницы, которые подлежали испытанию. Когда растени достигали стадии развити 2-3 листьев , наносили вместе антидот формулы 1 и гербицид. Через 21 день после нанесени оценивали состо ние растений и рассчитывали защитное действие антидота. Защитное действие - это разница между повреждением, вызванным действием гербицида на необработанное антидотом рас- тение и обработанного антидотом растени . Повреждение указано в процентах по отношению к необработанным растени м. Результаты представлены в табл.2. Таким образом за вленные средства обладают малой фитотоксичностыо его отношению к культурным растени м.
Claims (1)
- Формула изобретени Гербицидное средство, содержащееактивный ингредиент, смесь гербицида, сложного пропаргилового эфира 2(R)(5- хлор-3-фторпиридин-2-ил-окси)-фенокси - пропионовой кислоты с антидотом - производным фенилпиразолкарбоновой кислоты,и целевые добавки, отличающеес тем, что, с целью уменьшени фитотоксического действи гербицида на культурные растени , оно содержит в качестве производного фенилпиразолкарбоновой кислоты производное 1,5-дифенил-пиразол-З-карбоновой кислоты формулыCOOK(Кб)где Ra - водород, хлор в положении 2 или фтор в положении 3;(Rb)n - водород, фтор, хлор, бром в положении 2 или хлор в положени х 2 и 4;RI - водород, нормальный Ci-Сб-алкил, 2-метил-пропенил-З, гексеиил-6, циклогек- сил, циклогексилметил, 2-хлорбензил, фе- ноксиэтил, п и раз о л-1-и л-про пен и л-2, пиридинил-3, 5-метил-тиазол-4-ил-этил, ти- офен-2-ил-этил, метоксикарбонилметил, изопропиламмоний,при соотношении гербицида к антидоту 8:1- 1:4 и при следующем соотношении компонентов , мас.%:активный ингредиент-. 25-40;целевые добавки -остальное .ТаблицаФизико-химические свойства антидотов формулы (I)фъ(R&VЗащитное действие гербицидных средствN/1И v.COOK,Таблица 2Продолжение табл. 2Продолжение табл. 2Продолжение табл. 2А- 1-изопропил-3-(3-хлорфенил)-4-этоксикарбонил-пиразол Б - 1-метил-3-(3-хлорфенил)-4-этоксикарбонил-пиразол.Продолжение табл. 2
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH421786 | 1986-10-22 | ||
CH421586 | 1986-10-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
RU1837763C true RU1837763C (ru) | 1993-08-30 |
Family
ID=25694938
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU894614351A RU1837763C (ru) | 1986-10-22 | 1989-06-27 | Гербицидное средство |
Country Status (20)
Country | Link |
---|---|
US (3) | US5078780A (ru) |
EP (1) | EP0268554B1 (ru) |
JP (1) | JPS63115867A (ru) |
AR (1) | AR248279A1 (ru) |
AU (1) | AU591351B2 (ru) |
BR (1) | BR8705640A (ru) |
CA (1) | CA1301169C (ru) |
CS (1) | CS270230B2 (ru) |
DE (1) | DE3775527D1 (ru) |
DK (1) | DK550787A (ru) |
ES (1) | ES2037739T3 (ru) |
GR (1) | GR3003527T3 (ru) |
HU (1) | HU206683B (ru) |
IL (1) | IL84227A (ru) |
NZ (1) | NZ222233A (ru) |
PL (2) | PL151643B1 (ru) |
RU (1) | RU1837763C (ru) |
SU (1) | SU1597099A3 (ru) |
UA (2) | UA5583A1 (ru) |
ZA (1) | ZA877909B (ru) |
Families Citing this family (254)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2037739T3 (es) * | 1986-10-22 | 1993-07-01 | Ciba-Geigy Ag | Derivados del acido 1,5-difenilpirazol-3-carboxilico para la proteccion de plantas de cultivo. |
DE3817192A1 (de) * | 1988-05-20 | 1989-11-30 | Hoechst Ag | 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols |
PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
DE3939503A1 (de) * | 1989-11-30 | 1991-06-06 | Hoechst Ag | Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden |
US5700758A (en) * | 1989-11-30 | 1997-12-23 | Hoechst Aktiengesellschaft | Pyrazolines for protecting crop plants against herbicides |
ES2151879T3 (es) * | 1990-12-21 | 2001-01-16 | Aventis Cropscience Gmbh | Mezclas de herbicidas y antidotos. |
US5550147A (en) * | 1992-02-05 | 1996-08-27 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
WO1993017015A1 (en) | 1992-02-21 | 1993-09-02 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
EP0558448A1 (de) * | 1992-02-26 | 1993-09-01 | Ciba-Geigy Ag | 1,5-Diphenylpyrazol-3-Carbonsäure-Derivate als Antidots für Sulfonylharnstoffherbizide |
US5541148A (en) * | 1992-07-08 | 1996-07-30 | Ciba-Geigy Corporation | Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener |
WO1994013647A1 (en) * | 1992-12-15 | 1994-06-23 | The Du Pont Merck Pharmaceutical Company | (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents |
EE9400262A (et) * | 1993-12-08 | 1996-02-15 | Ciba-Geigy Ag | Selektiivne herbitsiidsegu ja selle kasutamise meetod |
US5438035A (en) * | 1994-06-24 | 1995-08-01 | American Cyanamid Company | Methods for controlling undesirable plant species with benzodiazepine compounds |
US6376424B1 (en) | 1998-01-21 | 2002-04-23 | Syngenta Crop Protection, Inc. | Herbicidal composition |
EP1413575B1 (en) * | 1999-08-03 | 2006-10-11 | Ortho-McNeil Pharmaceutical, Inc. | Process for preparing derivatives of ¬(1,5-diaryl)pyrazol-3-yl|propanoic acid |
EP2206703A1 (de) | 2008-12-30 | 2010-07-14 | Bayer CropScience AG | Pyrimidinderivate und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums |
US20040077650A1 (en) * | 2002-10-18 | 2004-04-22 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
US7129239B2 (en) * | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
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US7268133B2 (en) * | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
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AR048441A1 (es) | 2004-03-26 | 2006-04-26 | Syngenta Participations Ag | Una combinacion herbicida |
EP2064953A1 (de) | 2007-11-29 | 2009-06-03 | Bayer CropScience AG | Herbizid-Azol-Kombination |
EP2072512A1 (de) | 2007-12-20 | 2009-06-24 | Bayer CropScience AG | Herbizide Verbindungen auf Basis von N-Azinyl-N'-pyridylsulfonyl-harnstoffen |
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EP2112143A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience AG | 2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
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1987
- 1987-10-16 ES ES198787810598T patent/ES2037739T3/es not_active Expired - Lifetime
- 1987-10-16 EP EP87810598A patent/EP0268554B1/de not_active Expired - Lifetime
- 1987-10-16 US US07/109,667 patent/US5078780A/en not_active Expired - Fee Related
- 1987-10-16 DE DE8787810598T patent/DE3775527D1/de not_active Expired - Lifetime
- 1987-10-19 CS CS877532A patent/CS270230B2/cs unknown
- 1987-10-20 PL PL1987268311A patent/PL151643B1/pl unknown
- 1987-10-20 NZ NZ222233A patent/NZ222233A/xx unknown
- 1987-10-20 CA CA000549704A patent/CA1301169C/en not_active Expired - Lifetime
- 1987-10-20 PL PL1987280246A patent/PL151646B1/pl unknown
- 1987-10-20 IL IL84227A patent/IL84227A/xx not_active IP Right Cessation
- 1987-10-20 AR AR87309028A patent/AR248279A1/es active
- 1987-10-21 BR BR8705640A patent/BR8705640A/pt not_active Application Discontinuation
- 1987-10-21 DK DK550787A patent/DK550787A/da not_active Application Discontinuation
- 1987-10-21 HU HU874725A patent/HU206683B/hu not_active IP Right Cessation
- 1987-10-21 AU AU79972/87A patent/AU591351B2/en not_active Ceased
- 1987-10-21 SU SU874203524A patent/SU1597099A3/ru active
- 1987-10-21 UA UA4203524A patent/UA5583A1/uk unknown
- 1987-10-21 ZA ZA877909A patent/ZA877909B/xx unknown
- 1987-10-22 JP JP62267616A patent/JPS63115867A/ja active Pending
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1989
- 1989-03-20 US US07/325,834 patent/US5114462A/en not_active Expired - Fee Related
- 1989-03-20 US US07/325,833 patent/US4944790A/en not_active Expired - Lifetime
- 1989-06-27 RU SU894614351A patent/RU1837763C/ru active
- 1989-06-27 UA UA4614351A patent/UA19305A/ru unknown
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1992
- 1992-01-08 GR GR910402041T patent/GR3003527T3/el unknown
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US4944790A (en) | 1990-07-31 |
UA19305A (ru) | 1997-12-25 |
HUT45023A (en) | 1988-05-30 |
IL84227A0 (en) | 1988-03-31 |
SU1597099A3 (ru) | 1990-09-30 |
EP0268554B1 (de) | 1991-12-27 |
HU206683B (en) | 1992-12-28 |
GR3003527T3 (ru) | 1993-03-16 |
BR8705640A (pt) | 1988-05-31 |
PL151646B1 (en) | 1990-09-28 |
AU591351B2 (en) | 1989-11-30 |
PL151643B1 (en) | 1990-09-28 |
ZA877909B (ru) | 1988-04-22 |
JPS63115867A (ja) | 1988-05-20 |
CS753287A2 (en) | 1989-10-13 |
US5078780A (en) | 1992-01-07 |
AR248279A1 (es) | 1995-07-12 |
DK550787D0 (da) | 1987-10-21 |
US5114462A (en) | 1992-05-19 |
IL84227A (en) | 1992-01-15 |
NZ222233A (en) | 1989-09-27 |
ES2037739T3 (es) | 1993-07-01 |
AU7997287A (en) | 1988-04-28 |
EP0268554A2 (de) | 1988-05-25 |
UA5583A1 (uk) | 1994-12-28 |
DE3775527D1 (de) | 1992-02-06 |
DK550787A (da) | 1988-04-23 |
PL268311A1 (en) | 1988-09-01 |
EP0268554A3 (en) | 1988-06-08 |
CA1301169C (en) | 1992-05-19 |
CS270230B2 (en) | 1990-06-13 |
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