CY1548A - Insecticidal benzoylphenylureas - Google Patents
Insecticidal benzoylphenylureas Download PDFInfo
- Publication number
- CY1548A CY1548A CY1548A CY154891A CY1548A CY 1548 A CY1548 A CY 1548A CY 1548 A CY1548 A CY 1548A CY 154891 A CY154891 A CY 154891A CY 1548 A CY1548 A CY 1548A
- Authority
- CY
- Cyprus
- Prior art keywords
- formula
- compound
- chf
- salt
- chlorine
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 31
- 150000003839 salts Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 241000238631 Hexapoda Species 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
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- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 26
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- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
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- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
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- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
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- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
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- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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- 239000010459 dolomite Substances 0.000 description 1
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- 235000005489 dwarf bean Nutrition 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- IKHINJVRKROJSR-UHFFFAOYSA-N n-(2,5-dichloro-4-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(O)C=C1Cl IKHINJVRKROJSR-UHFFFAOYSA-N 0.000 description 1
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- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
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- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
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- 239000000575 pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
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- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH499384 | 1984-10-18 | ||
| CH536184 | 1984-11-08 | ||
| CH204885 | 1985-05-14 | ||
| CH350285 | 1985-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1548A true CY1548A (en) | 1991-03-22 |
Family
ID=27428360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1548A CY1548A (en) | 1984-10-18 | 1991-03-22 | Insecticidal benzoylphenylureas |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US4798837A (enExample) |
| EP (1) | EP0179022B1 (enExample) |
| JP (1) | JPH0347159A (enExample) |
| KR (1) | KR900006761B1 (enExample) |
| AU (1) | AU586194B2 (enExample) |
| BG (1) | BG60408B2 (enExample) |
| BR (1) | BR8505181A (enExample) |
| CA (1) | CA1242455A (enExample) |
| CY (1) | CY1548A (enExample) |
| DE (1) | DE3580444D1 (enExample) |
| DK (3) | DK160870C (enExample) |
| ES (1) | ES8609221A1 (enExample) |
| GB (3) | GB2165846B (enExample) |
| IL (1) | IL76708A (enExample) |
| LV (1) | LV10769B (enExample) |
| MY (2) | MY102685A (enExample) |
| NL (1) | NL930085I2 (enExample) |
| TR (1) | TR22452A (enExample) |
Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135953A (en) * | 1984-12-28 | 1992-08-04 | Ciba-Geigy | Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals |
| IT1201456B (it) * | 1985-08-22 | 1989-02-02 | Donegani Guido Ist | "n-(2,6-difluorobenzoil)-n'3,5-dicloro-4-(3,3,3-trifluoro-2-cloroprop-1-en-1-il)fenil urea ad attivita' insetticida |
| ES2038125T3 (es) * | 1985-10-14 | 1993-07-16 | Ciba-Geigy Ag | Benzoilfenilureas. |
| US5288756A (en) * | 1985-10-14 | 1994-02-22 | Ciba-Geigy Corporation | Benzoylphenylureas |
| EP0221847A3 (de) * | 1985-10-29 | 1988-03-23 | Ciba-Geigy Ag | Salze von Benzoylharnstoffen |
| ES2051770T3 (es) * | 1986-02-28 | 1994-07-01 | Ciba Geigy Ag | N-benzoil-n'-fenilureas, su obtencion y empleo en el control de parasitos. |
| DE3613062A1 (de) * | 1986-04-18 | 1987-10-29 | Hoechst Ag | N-benzoyl-n'-phenyl(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US5177110A (en) * | 1989-10-27 | 1993-01-05 | Ciba-Geigy Corporation | Injectable parasiticidal composition |
| AU631259B2 (en) * | 1989-12-18 | 1992-11-19 | Ciba-Geigy Ag | Formulations of benzoylphenyl ureas for combating ectoparasites |
| US5403814A (en) * | 1991-03-25 | 1995-04-04 | Ciba-Geigy Corporation | Sulfonylureas |
| AU8114294A (en) * | 1993-12-15 | 1995-07-03 | Ciba-Geigy Ag | Method of combating termites and other wood destructive insects |
| AU2616695A (en) * | 1994-06-08 | 1996-01-04 | Ciba-Geigy Ag | Synergistic composition |
| CH687732A5 (de) * | 1994-06-09 | 1997-02-14 | Ciba Geigy Ag | Verfahren zur Bekaempfung von Insekten. |
| US6323377B1 (en) | 1995-06-07 | 2001-11-27 | Syngenta Participations Ag | Oxidation process |
| US5945453A (en) * | 1996-11-08 | 1999-08-31 | Dow Agrosciences Llc | Benzoylphenylurea insecticides to control cockroaches |
| WO1998019995A1 (en) * | 1996-11-08 | 1998-05-14 | Dow Agrosciences Llc | New benzoylphenylurea insecticides ans methods of using them to control cockroaches |
| US5886221A (en) | 1997-11-03 | 1999-03-23 | Dow Agrosciences Llc | Benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites |
| DE19702207A1 (de) * | 1997-01-23 | 1998-07-30 | Bayer Ag | Verfahren zur Herstellung von p-Haloalkoxyanilinen |
| AU2387597A (en) * | 1997-04-17 | 1998-11-13 | Novartis Ag | Process for the hydroxylation of 1,4-dichlorobenzene |
| US5811461A (en) * | 1997-10-31 | 1998-09-22 | Dow Agrosciences Llc | Benzoylphenylurea insecticides and methods of using them to control cockroaches, ants, fleas, and termites |
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1985
- 1985-10-14 EP EP85810468A patent/EP0179022B1/de not_active Expired - Lifetime
- 1985-10-14 DE DE8585810468T patent/DE3580444D1/de not_active Expired - Lifetime
- 1985-10-14 IL IL76708A patent/IL76708A/xx not_active IP Right Cessation
- 1985-10-16 CA CA000493029A patent/CA1242455A/en not_active Expired
- 1985-10-16 GB GB08525516A patent/GB2165846B/en not_active Expired
- 1985-10-16 KR KR1019850007614A patent/KR900006761B1/ko not_active Expired
- 1985-10-16 TR TR34655/86A patent/TR22452A/xx unknown
- 1985-10-17 AU AU48818/85A patent/AU586194B2/en not_active Expired
- 1985-10-17 DK DK476585A patent/DK160870C/da not_active IP Right Cessation
- 1985-10-17 BR BR8505181A patent/BR8505181A/pt not_active IP Right Cessation
- 1985-10-17 ES ES547951A patent/ES8609221A1/es not_active Expired
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1987
- 1987-06-04 US US07/058,631 patent/US4798837A/en not_active Expired - Lifetime
- 1987-08-10 MY MYPI87001269A patent/MY102685A/en unknown
- 1987-10-15 GB GB08724215A patent/GB2195336B/en not_active Expired
- 1987-10-15 GB GB08724216A patent/GB2195635B/en not_active Expired
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1988
- 1988-10-24 US US07/262,121 patent/US4980506A/en not_active Expired - Lifetime
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1990
- 1990-03-12 JP JP2060891A patent/JPH0347159A/ja active Granted
- 1990-10-15 US US07/597,656 patent/US5107017A/en not_active Expired - Lifetime
- 1990-11-07 DK DK266990A patent/DK164850C/da not_active IP Right Cessation
-
1991
- 1991-03-22 CY CY1548A patent/CY1548A/en unknown
- 1991-08-09 DK DK144891A patent/DK164854C/da not_active IP Right Cessation
- 1991-12-17 MY MYPI91002333A patent/MY108591A/en unknown
-
1992
- 1992-06-15 BG BG096477A patent/BG60408B2/bg unknown
-
1993
- 1993-06-11 LV LVP-93-559A patent/LV10769B/en unknown
- 1993-06-22 NL NL930085C patent/NL930085I2/nl unknown
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