CS270567B2 - Fungicide and method of its active substance production - Google Patents
Fungicide and method of its active substance production Download PDFInfo
- Publication number
- CS270567B2 CS270567B2 CS873353A CS335387A CS270567B2 CS 270567 B2 CS270567 B2 CS 270567B2 CS 873353 A CS873353 A CS 873353A CS 335387 A CS335387 A CS 335387A CS 270567 B2 CS270567 B2 CS 270567B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- phenyl
- active ingredient
- carbon
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 239000000417 fungicide Substances 0.000 title abstract description 3
- 239000013543 active substance Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 27
- HRHFUHGNTSSIFS-UHFFFAOYSA-N 2h-thiazine 1-oxide Chemical class O=S1NC=CC=C1 HRHFUHGNTSSIFS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- -1 methoxycarbonylethoxy Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000004480 active ingredient Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- 125000005493 quinolyl group Chemical group 0.000 claims description 3
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- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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- 125000001041 indolyl group Chemical group 0.000 claims description 2
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- VJZNUICECYWOFV-UHFFFAOYSA-N o-phenyl carbamothioate Chemical compound NC(=S)OC1=CC=CC=C1 VJZNUICECYWOFV-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- LFPNUQDENLOJSK-UHFFFAOYSA-N thionine 1-oxide Chemical class O=S1C=CC=CC=CC=C1 LFPNUQDENLOJSK-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868611617A GB8611617D0 (en) | 1986-05-13 | 1986-05-13 | Fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS335387A2 CS335387A2 (en) | 1989-11-14 |
| CS270567B2 true CS270567B2 (en) | 1990-07-12 |
Family
ID=10597775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS873353A CS270567B2 (en) | 1986-05-13 | 1987-05-11 | Fungicide and method of its active substance production |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0245901B1 (de) |
| JP (1) | JPS62267276A (de) |
| KR (1) | KR940011459B1 (de) |
| CN (1) | CN1018455B (de) |
| AR (1) | AR242567A1 (de) |
| AT (1) | ATE79874T1 (de) |
| AU (1) | AU611853B2 (de) |
| BR (1) | BR8702378A (de) |
| CA (1) | CA1322551C (de) |
| CS (1) | CS270567B2 (de) |
| DE (1) | DE3781319T2 (de) |
| DK (1) | DK237987A (de) |
| EG (1) | EG18319A (de) |
| GB (1) | GB8611617D0 (de) |
| HU (1) | HU201225B (de) |
| IE (1) | IE61084B1 (de) |
| IL (1) | IL82476A0 (de) |
| NZ (1) | NZ220261A (de) |
| PL (1) | PL149431B1 (de) |
| PT (1) | PT84853B (de) |
| RU (1) | RU1814517C (de) |
| TR (1) | TR24449A (de) |
| ZA (1) | ZA873339B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4243818A1 (de) * | 1992-12-23 | 1994-06-30 | Bayer Ag | 5-Aryl-1,3-thiazin-Derivate |
| FR2798634B1 (fr) | 1999-09-17 | 2001-11-16 | Renault | Agencement de ceintures de securite pour vehicule automobile |
| WO2007049813A1 (ja) * | 2005-10-27 | 2007-05-03 | Teijin Pharma Limited | ベンゾ［ｂ］チオフェン誘導体およびその製造方法 |
| WO2007134625A1 (en) | 2006-05-24 | 2007-11-29 | Leibniz Institute For Natural Product Research And Infection Biology E.V. Hans-Knöll-Institut (Hki) | New benzothiazinone derivatives and their use as antibacterial agents |
| EP2181998B1 (de) | 2006-05-24 | 2012-09-19 | Leibniz-Institut für Naturstoff-Forschung und Infektionsbiologie e.V. -Hans-Knöll-Institut- (HKI) | Neues Benzothiazinon-Derivat und seine Verwendung als antibakterieller Wirkstoff |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD108541A1 (de) * | 1973-11-22 | 1974-09-20 | ||
| DE3118127A1 (de) * | 1981-05-07 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Neue sulfenamide, verfahren zu ihrer herstellung, ihre verwendung in arzneimitteln und deren herstellung |
| DE3309400A1 (de) * | 1983-03-16 | 1984-09-20 | Wella Ag | 3-amino-tetrahydro-1,3-thiazin-2,4-dione, ihre verwendung sowie diese verbindungen enthaltende hautbehandlungsmittel |
| JPS59199673A (ja) * | 1983-04-25 | 1984-11-12 | Sumitomo Chem Co Ltd | 含窒素複素環化合物、その製造法およびそれを有効成分とする有害生物防除剤 |
| JPS61171480A (ja) * | 1985-01-23 | 1986-08-02 | Meiji Seika Kaisha Ltd | ベンゾイソチアゾ−ル化合物、その製造法およびそれを有効成分とする植物病害防除剤 |
-
1986
- 1986-05-13 GB GB868611617A patent/GB8611617D0/en active Pending
-
1987
- 1987-04-29 EP EP87200817A patent/EP0245901B1/de not_active Expired - Lifetime
- 1987-04-29 AT AT87200817T patent/ATE79874T1/de not_active IP Right Cessation
- 1987-04-29 DE DE8787200817T patent/DE3781319T2/de not_active Expired - Fee Related
- 1987-05-05 CA CA000536369A patent/CA1322551C/en not_active Expired - Fee Related
- 1987-05-09 KR KR1019870004580A patent/KR940011459B1/ko not_active Expired - Fee Related
- 1987-05-11 CS CS873353A patent/CS270567B2/cs unknown
- 1987-05-11 IE IE121987A patent/IE61084B1/en not_active IP Right Cessation
- 1987-05-11 PT PT84853A patent/PT84853B/pt not_active IP Right Cessation
- 1987-05-11 AR AR87307519A patent/AR242567A1/es active
- 1987-05-11 DK DK237987A patent/DK237987A/da not_active Application Discontinuation
- 1987-05-11 JP JP62112651A patent/JPS62267276A/ja active Pending
- 1987-05-11 NZ NZ220261A patent/NZ220261A/en unknown
- 1987-05-11 AU AU72699/87A patent/AU611853B2/en not_active Ceased
- 1987-05-11 PL PL1987265625A patent/PL149431B1/pl unknown
- 1987-05-11 EG EG273/87A patent/EG18319A/xx active
- 1987-05-11 BR BR8702378A patent/BR8702378A/pt active Search and Examination
- 1987-05-11 TR TR87/0331A patent/TR24449A/xx unknown
- 1987-05-11 IL IL82476A patent/IL82476A0/xx not_active IP Right Cessation
- 1987-05-11 CN CN87104046A patent/CN1018455B/zh not_active Expired
- 1987-05-11 HU HU872111A patent/HU201225B/hu not_active IP Right Cessation
- 1987-05-11 ZA ZA873339A patent/ZA873339B/xx unknown
- 1987-05-11 RU SU874202609A patent/RU1814517C/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS335387A2 (en) | 1989-11-14 |
| PL265625A1 (en) | 1988-08-18 |
| TR24449A (tr) | 1991-10-10 |
| IE61084B1 (en) | 1994-09-21 |
| RU1814517C (ru) | 1993-05-07 |
| ZA873339B (en) | 1987-11-02 |
| AU611853B2 (en) | 1991-06-27 |
| HUT44695A (en) | 1988-04-28 |
| IE871219L (en) | 1987-11-13 |
| DE3781319T2 (de) | 1993-01-28 |
| ATE79874T1 (de) | 1992-09-15 |
| CA1322551C (en) | 1993-09-28 |
| PT84853A (en) | 1987-06-01 |
| EP0245901A2 (de) | 1987-11-19 |
| KR940011459B1 (ko) | 1994-12-15 |
| NZ220261A (en) | 1990-01-29 |
| BR8702378A (pt) | 1988-02-17 |
| AR242567A1 (es) | 1993-04-30 |
| CN87104046A (zh) | 1987-12-16 |
| EP0245901A3 (en) | 1989-03-22 |
| GB8611617D0 (en) | 1986-06-18 |
| IL82476A0 (en) | 1987-11-30 |
| DK237987A (da) | 1987-11-14 |
| PT84853B (pt) | 1990-02-08 |
| AU7269987A (en) | 1987-11-19 |
| DE3781319D1 (de) | 1992-10-01 |
| EP0245901B1 (de) | 1992-08-26 |
| KR870011115A (ko) | 1987-12-21 |
| JPS62267276A (ja) | 1987-11-19 |
| HU201225B (en) | 1990-10-28 |
| CN1018455B (zh) | 1992-09-30 |
| EG18319A (en) | 1992-09-30 |
| DK237987D0 (da) | 1987-05-11 |
| PL149431B1 (en) | 1990-02-28 |
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