CA1046518A - Procede de preparation de nouveaux derives organo-phosphores de la famille du thiazole - Google Patents
Procede de preparation de nouveaux derives organo-phosphores de la famille du thiazoleInfo
- Publication number
- CA1046518A CA1046518A CA217,458A CA217458A CA1046518A CA 1046518 A CA1046518 A CA 1046518A CA 217458 A CA217458 A CA 217458A CA 1046518 A CA1046518 A CA 1046518A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- carbon atoms
- hours
- diethoxythiophosphoryloxy
- reflux
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 150000007979 thiazole derivatives Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- -1 oxygen ketone Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- GUYXMSBMPTXFGD-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxy-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1N=C(OP(=S)(OCC)OCC)S2 GUYXMSBMPTXFGD-UHFFFAOYSA-N 0.000 claims 1
- 239000000642 acaricide Substances 0.000 abstract description 9
- 230000000895 acaricidal effect Effects 0.000 abstract description 8
- 230000000749 insecticidal effect Effects 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000256250 Spodoptera littoralis Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- DGSGISXCMTZRSX-UHFFFAOYSA-N 4h-cyclopenta[d][1,3]thiazole Chemical compound S1C=NC2=C1C=CC2 DGSGISXCMTZRSX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZJDBNSUHNOIEBS-UHFFFAOYSA-N 2-chlorocyclohexane-1,3-dione Chemical compound ClC1C(=O)CCCC1=O ZJDBNSUHNOIEBS-UHFFFAOYSA-N 0.000 description 1
- SXNMUZQWTWBSBL-UHFFFAOYSA-N 2h-cyclohepta[d][1,3]thiazole Chemical compound C1=CC=CC2=NCSC2=C1 SXNMUZQWTWBSBL-UHFFFAOYSA-N 0.000 description 1
- IXDPINWUMMWVHA-UHFFFAOYSA-N 3,4-dihydrocyclohepta[d][1,3]thiazol-2-one Chemical compound S1C(NC2=C1C=CC=CC2)=O IXDPINWUMMWVHA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- JPUAGPCLMGRSHO-UHFFFAOYSA-N CC(CCCC1Br)(C(O)=O)C1=O Chemical compound CC(CCCC1Br)(C(O)=O)C1=O JPUAGPCLMGRSHO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000578774 Homo sapiens MAP kinase-activated protein kinase 5 Proteins 0.000 description 1
- 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 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 102100028396 MAP kinase-activated protein kinase 5 Human genes 0.000 description 1
- 241001599018 Melanogaster Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- IGXVHEHYFFUMBM-UHFFFAOYSA-N S1C(NC2=C1C=CC2)=O Chemical compound S1C(NC2=C1C=CC2)=O IGXVHEHYFFUMBM-UHFFFAOYSA-N 0.000 description 1
- 241000254181 Sitophilus Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- XAAHBKSQAWTLDS-UHFFFAOYSA-N [O-]P(O)(O)=[S+]Cl Chemical compound [O-]P(O)(O)=[S+]Cl XAAHBKSQAWTLDS-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7400536A FR2256924B1 (en:Method) | 1974-01-08 | 1974-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1046518A true CA1046518A (fr) | 1979-01-16 |
Family
ID=9133208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA217,458A Expired CA1046518A (fr) | 1974-01-08 | 1975-01-07 | Procede de preparation de nouveaux derives organo-phosphores de la famille du thiazole |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3932433A (en:Method) |
| JP (1) | JPS50100055A (en:Method) |
| AR (1) | AR217035A1 (en:Method) |
| BE (1) | BE824152A (en:Method) |
| BR (1) | BR7500068A (en:Method) |
| CA (1) | CA1046518A (en:Method) |
| CH (1) | CH591513A5 (en:Method) |
| DD (1) | DD117588A5 (en:Method) |
| DE (1) | DE2500553A1 (en:Method) |
| DK (1) | DK141071B (en:Method) |
| EG (1) | EG11768A (en:Method) |
| FR (1) | FR2256924B1 (en:Method) |
| GB (1) | GB1437168A (en:Method) |
| HU (1) | HU171340B (en:Method) |
| IE (1) | IE41405B1 (en:Method) |
| IL (1) | IL46369A (en:Method) |
| IT (1) | IT1044113B (en:Method) |
| LU (1) | LU71600A1 (en:Method) |
| NL (1) | NL7500142A (en:Method) |
| PH (1) | PH11817A (en:Method) |
| SU (2) | SU543351A3 (en:Method) |
| TR (1) | TR18535A (en:Method) |
| ZA (1) | ZA75123B (en:Method) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159645A (en) * | 1960-12-29 | 1964-12-01 | Dow Chemical Co | Omcrion-thiazolyl omcrion-alkyl phosphoramido-thioates |
| BE755027A (fr) * | 1969-08-19 | 1971-02-19 | Bayer Ag | Esters d'acides thiazolo-(thiono)-phosphoriques et- phosphoriques, leurprocede de preparation et leur application comme insecticides et acaricides |
-
1974
- 1974-01-08 FR FR7400536A patent/FR2256924B1/fr not_active Expired
- 1974-12-12 DD DD182964A patent/DD117588A5/xx unknown
- 1974-12-26 US US05/536,424 patent/US3932433A/en not_active Expired - Lifetime
- 1974-12-30 IL IL46369A patent/IL46369A/en unknown
- 1974-12-30 DK DK686474AA patent/DK141071B/da unknown
-
1975
- 1975-01-02 GB GB13675A patent/GB1437168A/en not_active Expired
- 1975-01-03 HU HU75RO00000816A patent/HU171340B/hu unknown
- 1975-01-06 PH PH16676A patent/PH11817A/en unknown
- 1975-01-06 BR BR68/75A patent/BR7500068A/pt unknown
- 1975-01-07 CH CH9875A patent/CH591513A5/xx not_active IP Right Cessation
- 1975-01-07 NL NL7500142A patent/NL7500142A/xx not_active Application Discontinuation
- 1975-01-07 ZA ZA00750123A patent/ZA75123B/xx unknown
- 1975-01-07 CA CA217,458A patent/CA1046518A/fr not_active Expired
- 1975-01-07 IT IT47554/75A patent/IT1044113B/it active
- 1975-01-07 SU SU2102679A patent/SU543351A3/ru active
- 1975-01-07 BE BE152184A patent/BE824152A/xx unknown
- 1975-01-07 LU LU71600A patent/LU71600A1/xx unknown
- 1975-01-07 EG EG9/75A patent/EG11768A/xx active
- 1975-01-08 JP JP50004509A patent/JPS50100055A/ja active Pending
- 1975-01-08 AR AR257222A patent/AR217035A1/es active
- 1975-01-08 TR TR18535A patent/TR18535A/xx unknown
- 1975-01-08 IE IE44/75A patent/IE41405B1/en unknown
- 1975-01-08 DE DE19752500553 patent/DE2500553A1/de not_active Withdrawn
- 1975-08-01 SU SU752156933A patent/SU593643A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1044113B (it) | 1980-03-20 |
| DK686474A (en:Method) | 1975-09-01 |
| SU543351A3 (ru) | 1977-01-15 |
| DE2500553A1 (de) | 1975-07-10 |
| FR2256924B1 (en:Method) | 1976-10-08 |
| PH11817A (en) | 1978-07-18 |
| DK141071C (en:Method) | 1980-06-23 |
| CH591513A5 (en:Method) | 1977-09-30 |
| IL46369A0 (en) | 1975-03-13 |
| SU593643A3 (ru) | 1978-02-15 |
| BR7500068A (pt) | 1975-11-04 |
| BE824152A (fr) | 1975-07-07 |
| EG11768A (en) | 1977-12-31 |
| GB1437168A (en:Method) | 1976-05-26 |
| HU171340B (hu) | 1977-12-28 |
| AU7714475A (en) | 1976-07-08 |
| DD117588A5 (en:Method) | 1976-01-20 |
| NL7500142A (nl) | 1975-07-10 |
| FR2256924A1 (en:Method) | 1975-08-01 |
| IL46369A (en) | 1977-05-31 |
| TR18535A (tr) | 1977-03-16 |
| LU71600A1 (en:Method) | 1975-12-09 |
| US3932433A (en) | 1976-01-13 |
| ZA75123B (en) | 1976-01-28 |
| IE41405L (en) | 1975-07-08 |
| AR217035A1 (es) | 1980-02-29 |
| DK141071B (da) | 1980-01-07 |
| IE41405B1 (en) | 1980-01-02 |
| JPS50100055A (en:Method) | 1975-08-08 |
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