PL129418B1 - Fungicide and method of obtaining 5-aryloxy-5-azolilo-3,3-dimethyl-1-penten-4-ons and -ols - Google Patents
Fungicide and method of obtaining 5-aryloxy-5-azolilo-3,3-dimethyl-1-penten-4-ons and -ols Download PDFInfo
- Publication number
- PL129418B1 PL129418B1 PL1982237707A PL23770782A PL129418B1 PL 129418 B1 PL129418 B1 PL 129418B1 PL 1982237707 A PL1982237707 A PL 1982237707A PL 23770782 A PL23770782 A PL 23770782A PL 129418 B1 PL129418 B1 PL 129418B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- model
- ols
- aryloxy
- triazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- 230000000855 fungicidal effect Effects 0.000 title claims 2
- 239000000417 fungicide Substances 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims abstract 3
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims abstract 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract 2
- 125000000468 ketone group Chemical group 0.000 claims abstract 2
- 239000002184 metal Chemical class 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 101150118197 CSN1S1 gene Proteins 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- -1 nitro, cyano, phenyl Chemical group 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 241000221785 Erysiphales Species 0.000 abstract 1
- 241000221787 Erysiphe Species 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 235000007164 Oryza sativa Nutrition 0.000 abstract 1
- 241000896242 Podosphaera Species 0.000 abstract 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 235000009566 rice Nutrition 0.000 abstract 1
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (2)
1. Zastrzezenia patentowe 1. Srodek grzybobójczy zawierajacy substancje czynna znane nosniki i/lub zwiazki powierzchnio¬ wo czynne, znamienny tym, ze zawiera jako sub¬ stancje czynna 5-aryloksy-5-azolilo-3,3-dwumetylo- -lHpentem-4-ony i -ole o wzorze 1, w którym Ar oznacza ewentualnie podstawiony rodnik arylowy zwlaszcza oznacza rodnik fenylowy ewentualnie podstawiony atomem fluoru, chloru, bromu, rod¬ nikiem metylowym, etylowym, trójfluorometylo- wym, grupa metoksykarbonylowa, etoksykarbony- lowa, nitrowa, cyjanowa, rodnikiem fenylowym i chlorofenylowym, Az oznacza rodnik 1,2,4-triazol- -lHilowy, l,2,4-triazol-4-ilowy lub imidazol-1-ilowy i B oznacza grupe ketonowa lub grupe CH(OH).
2. Sposób wytwarzania 5-aryloksy-5-azolilo-3,3- -dwumetylo-l^penten-4-onów i -oli o wzorze 1, w którym Ar, Az i' B maja znaczenie podane w zastrz. 1, znamienny tym, ze chlorowcdeteroketo- ny o wzorze 2, w którym Ar ma znaczenie poda¬ ne w zastrz. 1 i Hal oznacza atom chloru lub bromu, poddaje sie reakcji z 1,2,4-triazolem lub imidazolem wobec akceptora kwasu ewentualnie w srodowisku rozcienczalnika i ewentualnie tak otrzy¬ mane pochodne ketonowe o wzorze 1 poddaje sie redukcji w znany sposób i ewentualnie jeszcze pod¬ daje sie reakcji addycji z kwasem lub sola me¬ talu. Ar-O-CH I Az CHa I ó B-C-CH=CH2 I CH: Ar-0-C-C-CH=CH2 CH: CH Hal WZÓR 1 WZÓR k ChU I * Ar-O-CH-CO-C-CH = CH? I I Hal • CHo (Br)Cl-CH. CHa I J C0-C-CH=CH- I 2 CH3 WZÓR 2 WZÓR 5 CH3 Ar-0-CH2-CO-C-CH=CH2 CHo CH: ci- IUn CH3 WZÓR 3 WZÓR 6129 418 CH- CHo cKO)-o-ch - co - c-CK = ch. Br CH0 WZÓR 7 CL^OrO-CH CHn 2-C0-C-CH = cH2 CH 3, CL-GH=C-C - CH. = CH l t 0 CH3 ó WZÓR 10 CH. I ó cl2c=ch-c - ch =ch2 \h3, WZÓR 8 WZÓR 11 CH, CL-CH.-CO-C-CH = CH. CH: CH- ClH^)-0 -CH-CO-C-CH = CH- N—' WZÓR 9 WZÓR 12129 418 CH 3 Cl~O-0"CH"C0"C"CH= CH2 N—N hQ-0-CH-CO-C-CH2 WZÓR 13 fTNTl CH3 •—N ^ ?H ?H3 WZÓR 16 Cl-^J)-0-CH-CH -C-CH = CH2 N Cl-^J-0-CH-CO-C-CH2a WZÓR V, N%N Ch3 N—^ ^ ?H ™3 WZÓR 17 Cl-(( )VO-CH- CH-C-CH,Br .N CH3 /" CH3 N^ ^- WZÓR 15 ffNn CH3 WZÓR 18199419 CH- Br // W CL // \N CL Cl WZÓR 19 WZÓR 20 Cl WZÓR 2U ci-/v^ WZÓR 21 Cl f--// v WZÓR 22 WZÓR 25 OO WZÓR 26129 418 Cl WZÓR 21 WZÓR 29 -N 1 WZÓR 31 WZÓR 28 -1 WZÓR 30 ci-- WZÓR 32 Cl H CH3 I -Oo-CH-CO-c-CH=CH2 ? fj\ ZaSada I I * N— -HBr Br CH3 CH3 "** Cl-^^-0-CH-CO-C-CH=CH2 N—J SCHEMAT 1129 418 /T\ ^ NaBH4 Cl-^J)-0-CH-CO-C-CH=CH2 —*• rN CH3 N—' OH CH3 ¦*" Cl-^3-°"CH~CH"c"CH=CH2 fl_j SCHEMAT 2 PZGraf. Koszalin A-246 85 A-4 Csna U9 zi PL PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813130435 DE3130435A1 (de) | 1981-08-01 | 1981-08-01 | 5-aryloxy-5-azolyl-3,3-dimethyl-1-penten-4-one und -ole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL237707A1 PL237707A1 (en) | 1983-03-28 |
| PL129418B1 true PL129418B1 (en) | 1984-05-31 |
Family
ID=6138307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1982237707A PL129418B1 (en) | 1981-08-01 | 1982-07-30 | Fungicide and method of obtaining 5-aryloxy-5-azolilo-3,3-dimethyl-1-penten-4-ons and -ols |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4514409A (pl) |
| EP (1) | EP0073331B1 (pl) |
| JP (1) | JPS5826873A (pl) |
| AT (1) | ATE19070T1 (pl) |
| AU (1) | AU8594882A (pl) |
| BR (1) | BR8204477A (pl) |
| CA (1) | CA1184560A (pl) |
| CS (1) | CS236677B2 (pl) |
| DD (1) | DD202613A5 (pl) |
| DE (2) | DE3130435A1 (pl) |
| DK (1) | DK342282A (pl) |
| ES (1) | ES8305731A1 (pl) |
| IL (1) | IL66420A (pl) |
| PL (1) | PL129418B1 (pl) |
| ZA (1) | ZA825519B (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3501245A1 (de) * | 1985-01-16 | 1986-07-17 | Bayer Ag | Azolyl-aroxymethyl-dimethylpentinole |
| CN107880862B (zh) * | 2017-11-07 | 2018-08-10 | 西南石油大学 | 一种提高承压能力的封堵剂及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2105490C3 (de) * | 1971-02-05 | 1979-06-13 | Bayer Ag, 5090 Leverkusen | 1 -Imidazolylketonderivate |
| US4147791A (en) * | 1972-01-11 | 1979-04-03 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| DE2333354C2 (de) * | 1973-06-30 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | 2-Aryloxy-2-(imidazol-1-yl)-äthanole sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| DE2632602A1 (de) * | 1976-07-20 | 1978-01-26 | Bayer Ag | Halogenierte 1-imidazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2632603A1 (de) * | 1976-07-20 | 1978-01-26 | Bayer Ag | Halogenierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2743767A1 (de) * | 1977-09-29 | 1979-04-12 | Bayer Ag | Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2918801A1 (de) * | 1979-05-10 | 1980-11-20 | Basf Ag | Carbinolether |
| DE3021551A1 (de) * | 1980-06-07 | 1981-12-24 | Bayer Ag, 5090 Leverkusen | 4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
-
1981
- 1981-08-01 DE DE19813130435 patent/DE3130435A1/de not_active Withdrawn
-
1982
- 1982-07-13 AU AU85948/82A patent/AU8594882A/en not_active Abandoned
- 1982-07-14 US US06/398,028 patent/US4514409A/en not_active Expired - Fee Related
- 1982-07-19 EP EP82106482A patent/EP0073331B1/de not_active Expired
- 1982-07-19 AT AT82106482T patent/ATE19070T1/de not_active IP Right Cessation
- 1982-07-19 DE DE8282106482T patent/DE3270398D1/de not_active Expired
- 1982-07-23 DD DD82241899A patent/DD202613A5/de unknown
- 1982-07-29 JP JP57131345A patent/JPS5826873A/ja active Pending
- 1982-07-29 IL IL66420A patent/IL66420A/xx unknown
- 1982-07-30 BR BR8204477A patent/BR8204477A/pt unknown
- 1982-07-30 DK DK342282A patent/DK342282A/da not_active Application Discontinuation
- 1982-07-30 ZA ZA825519A patent/ZA825519B/xx unknown
- 1982-07-30 PL PL1982237707A patent/PL129418B1/pl unknown
- 1982-07-30 CS CS825739A patent/CS236677B2/cs unknown
- 1982-07-30 ES ES514577A patent/ES8305731A1/es not_active Expired
- 1982-07-30 CA CA000408506A patent/CA1184560A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD202613A5 (de) | 1983-09-28 |
| DE3270398D1 (en) | 1986-05-15 |
| EP0073331A1 (de) | 1983-03-09 |
| IL66420A0 (en) | 1982-11-30 |
| EP0073331B1 (de) | 1986-04-09 |
| ES514577A0 (es) | 1983-04-16 |
| CS236677B2 (en) | 1985-05-15 |
| CA1184560A (en) | 1985-03-26 |
| DE3130435A1 (de) | 1983-02-17 |
| ES8305731A1 (es) | 1983-04-16 |
| IL66420A (en) | 1986-01-31 |
| US4514409A (en) | 1985-04-30 |
| ZA825519B (en) | 1983-06-29 |
| DK342282A (da) | 1983-02-02 |
| AU8594882A (en) | 1983-02-10 |
| PL237707A1 (en) | 1983-03-28 |
| ATE19070T1 (de) | 1986-04-15 |
| JPS5826873A (ja) | 1983-02-17 |
| BR8204477A (pt) | 1983-07-19 |
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