RU2059365C1 - Способ борьбы с сорняками - Google Patents
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
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Abstract
Изобретение относится к химическим способам борьбы с сорняками. Изобретение позволяет повысить гербицидную активность на 10 - 90% путем обработки растений или их биотопа производным OC - NR1 - C4 = CR5 - CON - C = CR3 - CH = CCI - C(COOR2) = CH в которой R1 - метил, этил, метоксикарбонил, R2 - этил, изопропил, н. бутил, R3 - водород, фтор, R4 - метил, этил, н. пропил, фторметил, трифторметил, пентафторэтил, R5 - водород, фтор, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен, в количестве 0,01 - 3 кг/га. По сравнению с известным способом, в котором используется 3-(2, 4-дихлорфенил)-1, 5, 6-тетрагидро-1-метил-2н-циклопента-[d] пиримидин-2, 4/3н/-дион. 2 табл.
Description
Изобретение относится к химическим способам защиты растений, конкретно к способу борьбы с сорняками путем обработки растений или места их произрастания производным 3-(4-хлорфенил)-2,4-диоксо-1,2,3,4-тетрагидропиримидина.
Целью изобретения является повышение эффективности способа.
П р и м е р 1. Получение соединений формулы (I):
где R1 метил, этил, метоксикарбонил;
R2 этил, изопропил или н. бутил;
R3 водород или фтор,
R4 метил, этил, н.пропил, монофторметил, трифторметил или пентафторэтил;
R5 водород, фтор, хлор или метил, или R4 и R5 совместно означают три- или тетраметилен.
где R1 метил, этил, метоксикарбонил;
R2 этил, изопропил или н. бутил;
R3 водород или фтор,
R4 метил, этил, н.пропил, монофторметил, трифторметил или пентафторэтил;
R5 водород, фтор, хлор или метил, или R4 и R5 совместно означают три- или тетраметилен.
К раствору 15,0 г изопропилового эфира 2-хлор-4-фтор-5-(3,6-дигидро-3,4-диметил-2,6-диоксо-1(2Н)-пиримидинил)-бензо йной кислоты в 100 мл уксусной кислоты при комнатной температуре с перемешиванием в течение одной минуты по каплям добавляют 6,3 г сульфурилхлорида. Температура при этом повышается примерно до 30оС. Затем массу перемешивают еще 15 мин при комнатной температуре, после чего ее выпаривают досуха под пониженным давлением. Остаток растворяют в этилацетате, после чего полученный раствор подряд промывают водным раствором бикарбоната натрия и водой. Органическую фазу высушивают безводным сульфатом натрия и выпаривают досуха. Полученный остаток перекристаллизовывают из смеси метиленхлорида и диэтилового эфира. В результате получают изопропиловый эфир 2-хлор-4-фтор-5-(5-хлор-3,6-дигидро-3,4-диметил-2,6-диоксо-1(2Н)-пиримидинил )-бензойной кислоты с Тпл 150-153оС (соединение 14).
Аналогично получают соединения (I), представленные в табл. 1.
Данные 1Н-ЯМР-анализа соединений (I): соединение N 4 (CDCl3, 60 Мгц): 7,88 ppm (д, 1Н), 7,38 ppm (д, 1Н), 5,77 ppm (С, 1Н), 5,30 ppm (м, 1Н), 3,50 ppm (С, 3Н), 2,36 ppm (С, 3Н), 1,40 ppm (д, 6Н).
Соединение 7 (CDCl3, 400 Мгц): 7,83 ppm (д, 1Н), 7,34 ppm 2,53 ppm (т. 2Н), 1,72 ppm (м, 2Н), 1,36 ppm (д, 6Н), 1,10 ppm (т, 3Н).
Соединение 8 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,34 ppm (д, 1Н), 5,75 ppm (с, 1Н), 5,25 ppm (М, 1Н), 3,45 ppm (с, 3Н), 2,61 ppm (м, 2Н), 1,36 ppm (д, 6Н), 1,31 ppm (т, 3Н).
Соединение 9 (CDCl3, 400 Мгц): 7,82 ppm (д, 1Н), 7,33 ppm (д, 1Н), 5,23 ppm (м, 1Н), 3,51 ppm (с, 3Н), 2,71 ppm (м, 2Н), 2,04 ppm (с, 3Н), 1,35 ppm (д, 6Н), 1,28 ppm (т, 3Н).
Соединение 10 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,37 ppm (д, 1Н), 6,38 ppm (с, 1Н), 5,25 ppm (м, 1Н), 3,57 ppm (д, 3Н), 1,36 ppm (д, 6Н).
Соединение 13 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,35 ppm (д, 1Н), 5,24 ppm (м, 1Н), 4,03 ppm (с, 3Н), 3,02 ppm (м, 2Н), 2,79 ppm (м, 2Н), 2,16 ppm (м, 2Н), 1,36 ppm (д, 6Н).
Соединение 16 (CDCl3, 400 Мгц): 7,84 ppm (д. 1Н), 7,39 ppm (д, 1Н), 5,25 ppm (м, 1Н), 3,62 ppm (м, 3Н), 1,37 ppm (д, 6Н).
Соединение 17 (CDCl3, 400 Мгц): 7,85 ppm (д, 1Н), 7,39 ppm (д, 1Н), 5,25 ppm (м, 1Н), 3,60 ppm (т, 3Н), 1,37 ppm (д, 6Н).
Приложение.
Соединение 18 (CДCl3, 400 Мгц): 7,86 ррм (д, 1Н), 7,39 ррм (д, 1Н), 5,25 ррм (м, 1Н), 3,60 ррм (т, 3Н), 1,37 ррм (д, 6Н).
Соединение 19 (СДCl3, 200 Мгц): 7,72 ррм (д, 1Н), 7,59 ррм (д, 1Н), 7,27 ррм (м, 1Н), 6,39 ррм (с, 1Н), 5,26 ррм (м, 1Н), 3,56 ррм (с, 3Н), 1,37 ррм (д, 6Н).
Соединение 20 (СДCl3, 400 Мгц): 7,90 ррм (д, 1Н), 7,39 ррм (д, 1Н), 6,38 ррм (с, 1Н), 3,57 ррм (с, 3Н), 1,38 ррм (т, 3Н).
Соединение 21 (ДМСО, 400 Мгц): 8,05 ррм (д, 1Н), 7,88 ррм (д, 1Н), 6,61 ррм (с, 1Н), 4,30 ррм (т, 2Н), 3,42 ррм (с, 3Н), 1,69 ррм (м, 2Н), 1,39 ррм (м, 2Н), 0,92 ррм (т, 3Н).
Соединение 22 (СДCl3, 60 Мгц): 7,92 ррм (д, 1Н), 7,40 ррм (д, 1Н), 5,76 ррм (с, 1Н), 5,28 ррм (м, 1Н), 3,98 ррм (м, 2Н), 2,35 ррм (с, 3Н), 1,34 ррм (т, 9Н).
П р и м е р 2. Семена подопытных сорняков засевают в стерилизованную глинистую почву на глубину 0,5-2,0 см. Земля находилась в горшках из пластмассы размером 7 х 7 х 7 см. Каждое из испытуемых веществ применяют в виде 1% -ного раствора в ацетоне, который незадолго до его применения разбавляют соответствующим количеством водопроводной воды. Кроме того, в каждой композиции прибавляют 5 об. ионилфенол-(8)этоксилата.
Распределенные по отдельным горшкам семена обрызгивают раствором испытуемого вещества. Затем подопытные сорняки культивируют в темной теплице при 17-19оС или в теплице с искусственным освещением при 20-25оС соответственно, причем период освещения составляет 16 ч в сутки. Относительная влажность воздуха составляет 40-90% Через 4 недели после обрызгивания определяют гербицидную эффективность каждого испытуемого вещества путем сравнения наблюдаемого некроза (уменьшение местопроизрастания) прорастающих из этих семян растений с некрозом растений из семян, которые не обрызгивали испытуемым веществом, но в остальном подвергали одинаковой обработке. Результаты представлены в таблице 2.
Таким образом, заявленный способ обладает высокой эффективностью при малых нормах расхода.
Claims (4)
- СПОСОБ БОРЬБЫ С СОРНЯКАМИ путем обработки растений или места их произрастания производным 3-(4-хлорфени)-2,4-диоксо-1,2,3,4-тетрагидропиримидина, отличающийся тем, что, с целью повышения эффективности способа, в качестве производного 3-(4-хлорфенил)-2,4-диоксо-1,2,3,4-тетрагидропиримидина используют соединения общей формулы
где R1 метил, этил, метоксикарбонил;
R2 этил, изопропил, н-бутил;
R3 водород, фтор;
R4 метил, этил, н-пропил, фторметил, трифторметил, пентафторэтил;
R5 водород, фтор, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен,
в количестве 0,01 3 кг/га.Приоритет по признакам. - 20.03.85 при R1 метил, метоксикарбонил; R2 этил, изопропил; R3 водород, фтор; R4 метил, этил, трифторметил; R5 водород, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен.
- 06.02.86 при R4 н-пропил, фторметил; R5 фтор.
- 14.03.86 при R1 этил; R2 н-бутил; R4 - пентафторэтил.
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Application Number | Priority Date | Filing Date | Title |
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LV930824A LV5358A3 (lv) | 1985-03-20 | 1993-06-30 | Nezalu apkarosanas panemiens |
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CH124085 | 1985-03-20 | ||
CH1240/85 | 1985-03-20 | ||
CH46086 | 1986-02-06 | ||
CH460/86 | 1986-02-06 |
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SU4027079 Division | 1985-03-20 | 1986-03-14 |
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RU2059365C1 true RU2059365C1 (ru) | 1996-05-10 |
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SU884355504A RU2059365C1 (ru) | 1985-03-20 | 1988-04-14 | Способ борьбы с сорняками |
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US (2) | US4746352A (ru) |
EP (1) | EP0195346B1 (ru) |
CN (1) | CN1013076B (ru) |
AR (1) | AR242952A1 (ru) |
AT (1) | ATE77619T1 (ru) |
AU (1) | AU591890B2 (ru) |
CA (1) | CA1277317C (ru) |
DE (1) | DE3685762D1 (ru) |
DK (1) | DK167280B1 (ru) |
ES (2) | ES8706130A1 (ru) |
FI (1) | FI93542C (ru) |
HU (1) | HU196110B (ru) |
IE (1) | IE58308B1 (ru) |
IL (1) | IL78155A0 (ru) |
NO (1) | NO171977C (ru) |
PT (1) | PT82226B (ru) |
RU (1) | RU2059365C1 (ru) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
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DK366887A (da) * | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | Pyrimidinderivater |
PH23853A (en) * | 1986-08-21 | 1989-11-23 | Pfizer | Pyridopyrimidinediones |
EP0323487B1 (de) * | 1987-06-19 | 1993-03-31 | Ciba-Geigy Ag | Heterocyclische verbindungen |
US5017211A (en) * | 1987-09-23 | 1991-05-21 | Ciba-Geigy Corporation | Heterocyclic compounds |
US6207830B1 (en) | 1987-09-23 | 2001-03-27 | Syngenta Crop Protection, Inc. | Process for the production of 3-aryl-uracils |
HUT51864A (ru) * | 1987-10-22 | 1990-06-28 | Hoffmann La Roche | |
US4943309A (en) * | 1988-09-06 | 1990-07-24 | Uniroyal Chemical Company, Inc. | Method of defoleating cotton plants employing 3-carbonylphenyl uracil derivatives |
US4927451A (en) * | 1988-12-30 | 1990-05-22 | Uniroyal Chemical Company, Inc. | 3-aryldihydrouracils |
US4981508A (en) * | 1989-01-23 | 1991-01-01 | Uniroyal Chemical Company, Inc. | 1,4-benzoxazin-3-one substituted uracils |
KR0150221B1 (ko) * | 1989-06-29 | 1998-10-15 | 베르너 발데크, 발트라우트 베케레 | 헤테로 고리 화합물 |
AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5084084A (en) * | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5314864A (en) * | 1989-09-26 | 1994-05-24 | Sumitomo Chemical Company, Limited | N-aminouracil derivatives, and their production and use |
JP3064374B2 (ja) * | 1989-10-02 | 2000-07-12 | 住友化学工業株式会社 | ウラシル誘導体、その製造法およびそれを有効成分とする除草剤 |
US5134145A (en) * | 1989-11-17 | 1992-07-28 | Uniroyal Chemical Company, Inc. | Pesticidal pyrimidinyl benzoic acids and esters |
US5134144A (en) * | 1989-11-20 | 1992-07-28 | Uniroyal Chemical Company, Inc. | Pesticidal 3-arylpyrimidinyl ethers and thioethers |
EP0438209B1 (en) * | 1990-01-18 | 1994-09-21 | Nissan Chemical Industries, Limited | Uracil derivatives and pesticides containing the same as active ingredient |
US4979982A (en) * | 1990-02-02 | 1990-12-25 | Uniroyal Chemical Company, Inc. | Herbicidal cinnamic ester uracils |
US5176735A (en) * | 1990-06-28 | 1993-01-05 | Uniroyal Chemical Company, Inc. | Method of desiccating plants employing 3-carbonylphenyl uracil derivatives |
US5266554A (en) * | 1990-08-31 | 1993-11-30 | Ciba-Geigy Corporation | Heterocyclic compounds |
EP0473551A1 (de) * | 1990-08-31 | 1992-03-04 | Ciba-Geigy Ag | 3-Aryluracil-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Unkrautbekämpfungsmittel |
BR9104045A (pt) * | 1990-09-21 | 1992-06-09 | Sumitomo Chemical Co | Composto,processos para sua preparacao,composto intermediario,composicao herbicida,processo para exterminio de ervas daninhas indesejadas e uso do dito primeiro composto |
DE4035599A1 (de) * | 1990-11-06 | 1992-05-07 | Dresden Arzneimittel | Neue 5-(phenoxyalkanoylamino)-uracile, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
EP0489480A1 (en) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5153316A (en) * | 1991-06-04 | 1992-10-06 | Crouse Gary D | Intermediates for herbicidal phenylimidazolones |
US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
JPH05125057A (ja) * | 1991-11-01 | 1993-05-21 | Sumitomo Chem Co Ltd | 1−フエニル−4−トリフルオロメチルウラシル誘導体およびそれを有効成分とする除草剤 |
US5336663A (en) * | 1991-11-13 | 1994-08-09 | Ciba-Geigy Corporation | 3-aryluracil derivatives and their use for weed control |
JPH0687835A (ja) * | 1992-07-17 | 1994-03-29 | Rohm & Haas Co | 除草性2−アリール−5,6−縮合環−ピリミジン |
BR9305683A (pt) * | 1992-10-23 | 1996-12-03 | Ciba Geigy Ag | Derivados de 3-ariluracila e o uso dos mesmos para controle de ervas daninhas |
AU6677394A (en) * | 1993-04-21 | 1994-11-08 | Ciba-Geigy Ag | 3-aryluracil derivatives and their use as herbicides |
US5399543A (en) * | 1993-04-21 | 1995-03-21 | Fmc Corporation | 3-[4-(phenylmethoxy)phenyl]-1-substituted-6-haloalkyl-uracil herbicides |
US5502177A (en) * | 1993-09-17 | 1996-03-26 | Gilead Sciences, Inc. | Pyrimidine derivatives for labeled binding partners |
US5486521A (en) * | 1994-03-21 | 1996-01-23 | Uniroyal Chemical Company, Inc. | Pyrimidinyl aryl ketone oximes |
CA2189963A1 (en) * | 1994-05-18 | 1995-11-23 | Haruhiko Kikuchi | Novel pyrimidine derivative |
US5527764A (en) * | 1994-09-15 | 1996-06-18 | Uniroyal Chemical Company, Inc. | 3-arylthionouracils useful as herbicides, defoliants, and desiccants |
JP2001521027A (ja) | 1997-10-27 | 2001-11-06 | アイエスケー・アメリカズ・インコーポレーティッド | 置換ベンゼン化合物、それらの製造方法並びにそれらを含有する除草剤組成物及び落葉剤組成物 |
AR023523A1 (es) | 1999-04-19 | 2002-09-04 | Syngenta Participations Ag | Tratamiento herbicida para semillas |
IL148464A0 (en) * | 2000-05-04 | 2002-09-12 | Basf Ag | Uracil substituted phenyl sulfamoyl carboxamides |
CN100344628C (zh) * | 2005-03-29 | 2007-10-24 | 沈阳化工研究院 | 吡唑并嘧啶酮类化合物及其应用 |
CN100360509C (zh) * | 2005-04-15 | 2008-01-09 | 南开大学 | 用作除草剂的1-嘧啶酮基-4-氯-5-苯甲酸酯类化合物及其制备方法 |
US7671254B2 (en) * | 2005-08-25 | 2010-03-02 | The Board Of Trustees Of The University Of Illinois | Herbicide resistance gene, compositions and methods |
US7842856B2 (en) | 2005-08-25 | 2010-11-30 | The Board Of Trustees Of The University Of Illinois | Herbicide resistance gene, compositions and methods |
CN112574126B (zh) * | 2020-12-11 | 2022-03-11 | 南京正荣医药化学有限公司 | 一种苯嘧磺草胺中间体的制备方法 |
GB202209303D0 (en) | 2022-06-24 | 2022-08-10 | Redag Crop Prot Ltd | Agricultural chemicals |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3330640A (en) * | 1964-05-27 | 1967-07-11 | Du Pont | Method for the control of undesirable vegetation |
IL32113A (en) * | 1968-05-13 | 1973-10-25 | Du Pont | 1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them |
DE2005326A1 (de) * | 1970-02-06 | 1971-08-12 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Harnstoffderivate |
ES442992A1 (es) * | 1974-12-02 | 1977-08-01 | Scherico Ltd | Un procedimiento para preparar 2-anilino-oxazolinas. |
GR68935B (ru) * | 1976-03-31 | 1982-03-29 | Takeda Chemical Industries Ltd | |
US4266056A (en) * | 1978-04-07 | 1981-05-05 | Zoecon Corporation | Phenyl uracils |
GB2043629B (en) * | 1978-12-14 | 1982-11-17 | Zoecon Corp | Pesticidal compositions comprising 1-phenyl-3-polyhaloalkylthio-orpolyhalovinylthio-uracils and processes for treating plants |
DE3100911A1 (de) * | 1981-01-14 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenylharnstoffe und ihre verwendung zur bekaempfung von insekten |
DK366887A (da) * | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | Pyrimidinderivater |
EP0260621A3 (de) * | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung |
-
1986
- 1986-03-07 DK DK106786A patent/DK167280B1/da not_active Application Discontinuation
- 1986-03-10 EP EP86103188A patent/EP0195346B1/de not_active Expired - Lifetime
- 1986-03-10 AT AT86103188T patent/ATE77619T1/de not_active IP Right Cessation
- 1986-03-10 DE DE8686103188T patent/DE3685762D1/de not_active Expired - Lifetime
- 1986-03-10 US US06/837,986 patent/US4746352A/en not_active Expired - Fee Related
- 1986-03-13 FI FI861044A patent/FI93542C/fi not_active IP Right Cessation
- 1986-03-14 IL IL78155A patent/IL78155A0/xx not_active IP Right Cessation
- 1986-03-17 HU HU861093A patent/HU196110B/hu not_active IP Right Cessation
- 1986-03-19 CN CN86101792A patent/CN1013076B/zh not_active Expired
- 1986-03-19 CA CA000504505A patent/CA1277317C/en not_active Expired - Lifetime
- 1986-03-19 PT PT82226A patent/PT82226B/pt not_active IP Right Cessation
- 1986-03-19 IE IE70886A patent/IE58308B1/en not_active IP Right Cessation
- 1986-03-19 ES ES553138A patent/ES8706130A1/es not_active Expired
- 1986-03-19 NO NO861080A patent/NO171977C/no unknown
- 1986-03-20 AU AU54981/86A patent/AU591890B2/en not_active Ceased
- 1986-03-28 AR AR86303408A patent/AR242952A1/es active
- 1986-12-01 ES ES557231A patent/ES8800172A1/es not_active Expired
-
1988
- 1988-01-25 US US07/148,315 patent/US4760163A/en not_active Expired - Fee Related
- 1988-04-14 RU SU884355504A patent/RU2059365C1/ru active
Also Published As
Publication number | Publication date |
---|---|
ES553138A0 (es) | 1987-06-01 |
HUT42275A (en) | 1987-07-28 |
CN1013076B (zh) | 1991-07-10 |
FI861044A (fi) | 1986-09-21 |
DK106786D0 (da) | 1986-03-07 |
ES557231A0 (es) | 1987-10-16 |
EP0195346B1 (de) | 1992-06-24 |
AU591890B2 (en) | 1989-12-21 |
NO171977C (no) | 1993-05-26 |
US4760163A (en) | 1988-07-26 |
ES8706130A1 (es) | 1987-06-01 |
FI93542B (fi) | 1995-01-13 |
IL78155A0 (en) | 1986-07-31 |
PT82226B (pt) | 1988-07-29 |
PT82226A (en) | 1986-04-01 |
IE860708L (en) | 1986-09-20 |
NO861080L (no) | 1986-09-22 |
EP0195346A3 (en) | 1987-09-02 |
ATE77619T1 (de) | 1992-07-15 |
FI861044A0 (fi) | 1986-03-13 |
AR242952A1 (es) | 1993-06-30 |
CA1277317C (en) | 1990-12-04 |
FI93542C (fi) | 1995-04-25 |
CN86101792A (zh) | 1986-11-12 |
HU196110B (en) | 1988-10-28 |
NO171977B (no) | 1993-02-15 |
ES8800172A1 (es) | 1987-10-16 |
DE3685762D1 (de) | 1992-07-30 |
US4746352A (en) | 1988-05-24 |
AU5498186A (en) | 1986-09-25 |
DK106786A (da) | 1986-09-21 |
IE58308B1 (en) | 1993-09-08 |
EP0195346A2 (de) | 1986-09-24 |
DK167280B1 (da) | 1993-10-04 |
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