HU180915B - Substituted insecticide preparation consists of pyrazoline agent and method for producing 1,3,4-disubstituted pyrazoline derivatives - Google Patents
Substituted insecticide preparation consists of pyrazoline agent and method for producing 1,3,4-disubstituted pyrazoline derivatives Download PDFInfo
- Publication number
- HU180915B HU180915B HU77PI557A HUPI000557A HU180915B HU 180915 B HU180915 B HU 180915B HU 77PI557 A HU77PI557 A HU 77PI557A HU PI000557 A HUPI000557 A HU PI000557A HU 180915 B HU180915 B HU 180915B
- Authority
- HU
- Hungary
- Prior art keywords
- pyrazoline
- substituted
- chlorophenyl
- formula
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003219 pyrazolines Chemical class 0.000 title claims description 14
- 239000002917 insecticide Substances 0.000 title abstract description 4
- 239000003795 chemical substances by application Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title 1
- -1 cyano-piperidino Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 21
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920001732 Lignosulfonate Polymers 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 claims 1
- 229910052622 kaolinite Inorganic materials 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
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- 238000009472 formulation Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
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- 241000255969 Pieris brassicae Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- ZKWDQFQDWJGOMB-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(3-cyanopropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC#N)C1 ZKWDQFQDWJGOMB-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- 230000000855 fungicidal effect Effects 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
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- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
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- LLXXDGFFMPHRJE-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-cyanophenyl)-4-[2-(diethylamino)ethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CCN(CC)CCC1CN(C(=O)NC=2C=CC(=CC=2)C#N)N=C1C1=CC=C(Cl)C=C1 LLXXDGFFMPHRJE-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- NIBJHMAOWHBWKO-UHFFFAOYSA-N N,5-bis(4-chlorophenyl)-4-(3-piperidin-1-ylpropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCN2CCCCC2)C1 NIBJHMAOWHBWKO-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- CYPNBACJQNTDIB-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-piperidin-1-ylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCN2CCCCC2)C1 CYPNBACJQNTDIB-UHFFFAOYSA-N 0.000 description 2
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- SFSMJOOADNHZRV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[(dimethylamino)methyl]-4-piperidin-1-ylbutan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(CN(C)C)CCN1CCCCC1 SFSMJOOADNHZRV-UHFFFAOYSA-N 0.000 description 1
- QVOUYLNWXDTCHX-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-piperidin-1-ylbutan-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)CCCN1CCCCC1 QVOUYLNWXDTCHX-UHFFFAOYSA-N 0.000 description 1
- NFWBJASDXMLSCI-UHFFFAOYSA-N 1-[2-(3,4-dihydropyrazol-2-yl)ethyl]piperidine Chemical compound N1(CCCCC1)CCN1N=CCC1 NFWBJASDXMLSCI-UHFFFAOYSA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- VXOXFIZOHUKABN-UHFFFAOYSA-L magnesium N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound C(CNC([S-])=S)NC([S-])=S.[Mg+2] VXOXFIZOHUKABN-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7600178,A NL183400C (nl) | 1976-01-09 | 1976-01-09 | Werkwijze ter bereiding van een insecticide preparaat dat een pyrazoline-verbinding bevat en werkwijze ter bereiding van een pyrazoline-verbinding met insecticide werking. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180915B true HU180915B (en) | 1983-05-30 |
Family
ID=19825416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77PI557A HU180915B (en) | 1976-01-09 | 1977-01-06 | Substituted insecticide preparation consists of pyrazoline agent and method for producing 1,3,4-disubstituted pyrazoline derivatives |
Country Status (28)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014810A3 (en) | 1979-01-18 | 1980-11-26 | Fbc Limited | Pesticidal pyrazoles, their production, compositions and uses, as well as intermediates and their preparation |
| EP0021506B1 (en) * | 1979-07-03 | 1983-09-07 | Duphar International Research B.V | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds |
| JPS57209275A (en) * | 1981-06-19 | 1982-12-22 | Nissan Chem Ind Ltd | Novel pyrazoline derivative, its preparation, and vermin-controlling agent containing said derivative as active component |
| GB2093836B (en) * | 1981-02-17 | 1984-09-05 | Nissan Chemical Ind Ltd | Insecticidal pyrazoline derivatives |
| ATE14309T1 (de) * | 1981-05-12 | 1985-08-15 | Duphar Int Res | Pyrazolinderivate, verfahren zu ihrer herstellung und diese enthaltende insektizide praeparate. |
| ZA858002B (en) * | 1984-10-25 | 1987-04-29 | Fmc Corp | Pyrazoline insecticides |
| AU556949B2 (en) * | 1984-10-25 | 1986-11-27 | Fmc Corporation | Pyrozoline insecticides |
| EP0182746A3 (de) * | 1984-11-16 | 1988-10-12 | Ciba-Geigy Ag | Pyrazolinderivate |
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| DE3638631A1 (de) * | 1986-11-11 | 1988-05-26 | Schering Ag | Pyrazoline, ihre herstellung und ihre verwendung als mittel mit insektizider und akarizider wirkung |
| DE4032089A1 (de) * | 1990-01-24 | 1991-07-25 | Bayer Ag | Substituierte pyrazolinderivate |
| DE4217862A1 (de) * | 1991-08-28 | 1993-03-04 | Bayer Ag | Substituierte pyrazoline |
| DE4217863A1 (de) * | 1991-08-28 | 1993-03-04 | Bayer Ag | Substituierte pyrazoline |
| EP0629201A1 (en) * | 1992-03-02 | 1994-12-21 | E.I. Du Pont De Nemours And Company | Arthropodicidal amides |
| DE4218745A1 (de) * | 1992-06-04 | 1993-12-09 | Schering Ag | 1-(4-Cyanophenyl-carbamoyl)-pyrazoline |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795264A (fr) * | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux composes de pyrazoline a activite insecticide |
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| DE2700288A1 (de) * | 1977-01-05 | 1978-07-13 | Bayer Ag | Phenylcarbamoyl-pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2700289A1 (de) * | 1977-01-05 | 1978-07-06 | Bayer Ag | Substituierte phenylcarbamoyl-2- pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
-
1976
- 1976-01-09 NL NLAANVRAGE7600178,A patent/NL183400C/xx not_active IP Right Cessation
-
1977
- 1977-01-03 ZA ZA00770014A patent/ZA7714B/xx unknown
- 1977-01-04 SE SE7700067A patent/SE435176B/xx unknown
- 1977-01-05 IT IT19085/77A patent/IT1076002B/it active
- 1977-01-05 DE DE19772700258 patent/DE2700258A1/de not_active Ceased
- 1977-01-06 HU HU77PI557A patent/HU180915B/hu not_active IP Right Cessation
- 1977-01-06 CH CH12977A patent/CH631870A5/de not_active IP Right Cessation
- 1977-01-06 IE IE24/77A patent/IE45012B1/en unknown
- 1977-01-06 GB GB356/77A patent/GB1570635A/en not_active Expired
- 1977-01-06 IL IL51225A patent/IL51225A/xx unknown
- 1977-01-06 DD DD7700196841A patent/DD129396A5/xx unknown
- 1977-01-06 DK DK5377A patent/DK142985C/da active
- 1977-01-06 NZ NZ183006A patent/NZ183006A/xx unknown
- 1977-01-06 YU YU00018/77A patent/YU1877A/xx unknown
- 1977-01-07 PL PL1977195195A patent/PL110077B1/pl unknown
- 1977-01-07 ES ES454857A patent/ES454857A1/es not_active Expired
- 1977-01-07 PT PT66039A patent/PT66039B/pt unknown
- 1977-01-07 GR GR52531A patent/GR63086B/el unknown
- 1977-01-07 AT AT5177A patent/AT353260B/de not_active IP Right Cessation
- 1977-01-07 FR FR7700371A patent/FR2337715A1/fr active Granted
- 1977-01-07 PL PL1977212934A patent/PL109512B1/pl unknown
- 1977-01-07 BE BE173949A patent/BE850220A/xx unknown
- 1977-01-07 CS CS77116A patent/CS205031B2/cs unknown
- 1977-01-08 JP JP110777A patent/JPS5287166A/ja active Granted
- 1977-01-09 EG EG15/77A patent/EG13910A/xx active
- 1977-01-10 BR BR7700133A patent/BR7700133A/pt unknown
- 1977-01-10 AU AU21188/77A patent/AU510358B2/en not_active Expired
- 1977-01-10 CA CA269,399A patent/CA1111048A/en not_active Expired
- 1977-01-21 OA OA56052A patent/OA05550A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |