IL27678A - Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them - Google Patents
Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing themInfo
- Publication number
- IL27678A IL27678A IL27678A IL2767867A IL27678A IL 27678 A IL27678 A IL 27678A IL 27678 A IL27678 A IL 27678A IL 2767867 A IL2767867 A IL 2767867A IL 27678 A IL27678 A IL 27678A
- Authority
- IL
- Israel
- Prior art keywords
- lower alkyl
- hydrogen
- compound
- pyrimidine
- atom
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 68
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 5
- 230000000749 insecticidal effect Effects 0.000 title claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 150000003230 pyrimidines Chemical class 0.000 claims description 21
- -1 alkaline earth metal salt Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 241000238631 Hexapoda Species 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 206010061217 Infestation Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000000080 wetting agent Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003337 fertilizer Substances 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 230000002538 fungal effect Effects 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000007530 organic bases Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims 4
- 239000012429 reaction media Substances 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
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- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 229940093499 ethyl acetate Drugs 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 4
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
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- 208000031888 Mycoses Diseases 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1426766 | 1966-03-31 | ||
| GB14268/66A GB1129563A (en) | 1966-03-31 | 1966-03-31 | Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them |
| GB1426966 | 1966-03-31 | ||
| GB14266/66A GB1129797A (en) | 1966-03-31 | 1966-03-31 | Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27678A true IL27678A (en) | 1972-07-26 |
Family
ID=35530797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27678A IL27678A (en) | 1966-03-31 | 1967-03-23 | Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4041157A (de) |
| BE (2) | BE696467A (de) |
| DE (2) | DE1695271B2 (de) |
| FR (2) | FR1548278A (de) |
| GB (2) | GB1129797A (de) |
| IL (1) | IL27678A (de) |
| NL (2) | NL6704603A (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1388401A (en) * | 1971-05-06 | 1975-03-26 | Ici Ltd | Pesticidal pyrimidinyl esters of phosphorus acids |
| GB1390282A (en) * | 1972-12-18 | 1975-04-09 | Ici Ltd | Phosphorus-containing pyrimidine derivatives |
| GB1441206A (en) * | 1974-05-20 | 1976-06-30 | Ici Ltd | Process for preparing 2-amino-4-hydroxypyrimidine derivatives |
| DE2619450A1 (de) * | 1976-05-03 | 1977-11-24 | Bayer Ag | Diphosphorylierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2620089A1 (de) * | 1976-05-06 | 1977-11-24 | Bayer Ag | Substituierte pyrimidin-bis- eckige klammer auf (thiono)(thiol)-phosphor(phosphon)-saeureester eckige klammer zu, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
| US4892732A (en) * | 1987-11-27 | 1990-01-09 | The Dow Chemical Company | Method and composition for enhancing the insecticidal activity of certain organophosphorus compounds |
| US6878697B2 (en) | 2001-06-21 | 2005-04-12 | Ariad Pharmaceuticals, Inc. | Phenylamino-pyrimidines and uses thereof |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| EP2300013B2 (de) | 2008-05-21 | 2024-11-13 | Takeda Pharmaceutical Company Limited | Phosphor-derivate als kinase-inhibitoren |
| AU2012250517B2 (en) | 2011-05-04 | 2016-05-19 | Takeda Pharmaceutical Company Limited | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| AU2013204563B2 (en) | 2012-05-05 | 2016-05-19 | Takeda Pharmaceutical Company Limited | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129225C (de) * | 1963-03-28 | 1900-01-01 | ||
| US3906094A (en) * | 1966-03-31 | 1975-09-16 | Ici Ltd | Method and composition for combatting fungus with fungicidally-active pyrimidine derivatives |
| US3651224A (en) * | 1967-09-21 | 1972-03-21 | Ici Ltd | Pesticidal pyrimidine derivative |
| GB1257634A (de) * | 1968-08-07 | 1971-12-22 |
-
1966
- 1966-03-31 GB GB14266/66A patent/GB1129797A/en not_active Expired
- 1966-03-31 GB GB14268/66A patent/GB1129563A/en not_active Expired
-
1967
- 1967-03-23 IL IL27678A patent/IL27678A/en unknown
- 1967-03-28 DE DE1967J0033313 patent/DE1695271B2/de active Granted
- 1967-03-29 DE DE1695273A patent/DE1695273C3/de not_active Expired
- 1967-03-31 FR FR1548278D patent/FR1548278A/fr not_active Expired
- 1967-03-31 NL NL6704603A patent/NL6704603A/xx not_active Application Discontinuation
- 1967-03-31 NL NL6704665A patent/NL6704665A/xx not_active Application Discontinuation
- 1967-03-31 BE BE696467D patent/BE696467A/xx unknown
- 1967-03-31 BE BE696468D patent/BE696468A/xx unknown
- 1967-03-31 FR FR1548279D patent/FR1548279A/fr not_active Expired
-
1975
- 1975-08-27 US US05/608,331 patent/US4041157A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695273A1 (de) | 1971-06-03 |
| FR1548278A (de) | 1968-12-06 |
| NL6704603A (de) | 1967-10-02 |
| DE1695273B2 (de) | 1977-10-27 |
| US4041157A (en) | 1977-08-09 |
| DE1695271A1 (de) | 1971-06-03 |
| DE1695273C3 (de) | 1978-06-29 |
| FR1548279A (de) | 1968-12-06 |
| DE1695271B2 (de) | 1976-12-09 |
| BE696468A (de) | 1967-10-02 |
| BE696467A (de) | 1967-10-02 |
| GB1129797A (en) | 1968-10-09 |
| NL6704665A (de) | 1967-10-02 |
| GB1129563A (en) | 1968-10-09 |
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