DE2606761C2 - Monoester der thiophosphorigen Säure, Verfahren zu ihrer Herstellung und von Metallthiophosphiten sowie fungicide Zusammensetzungen und Verwendung der letzteren - Google Patents
Monoester der thiophosphorigen Säure, Verfahren zu ihrer Herstellung und von Metallthiophosphiten sowie fungicide Zusammensetzungen und Verwendung der letzterenInfo
- Publication number
- DE2606761C2 DE2606761C2 DE2606761A DE2606761A DE2606761C2 DE 2606761 C2 DE2606761 C2 DE 2606761C2 DE 2606761 A DE2606761 A DE 2606761A DE 2606761 A DE2606761 A DE 2606761A DE 2606761 C2 DE2606761 C2 DE 2606761C2
- Authority
- DE
- Germany
- Prior art keywords
- compositions according
- active ingredient
- ammonium
- methyl
- thiophosphite
- 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
- 239000000203 mixture Substances 0.000 title claims description 34
- 229910052751 metal Inorganic materials 0.000 title claims description 10
- 239000002184 metal Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 230000000855 fungicidal effect Effects 0.000 title claims description 6
- TYQTYRXEMJXFJG-UHFFFAOYSA-N phosphorothious acid Chemical compound OP(O)S TYQTYRXEMJXFJG-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 alkaline earth metal cation Chemical class 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 230000003449 preventive effect Effects 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 241000235349 Ascomycota Species 0.000 claims description 4
- 241000221198 Basidiomycota Species 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- DIZHXRWYGQRFJZ-UHFFFAOYSA-N P(SCC)([O-])[O-].[Mg+2] Chemical compound P(SCC)([O-])[O-].[Mg+2] DIZHXRWYGQRFJZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 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 claims description 3
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- 239000003513 alkali Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- OISOEVXHXBNOKU-UHFFFAOYSA-N calcium dioxido(propan-2-ylsulfanyl)phosphane Chemical compound P(SC(C)C)([O-])[O-].[Ca+2] OISOEVXHXBNOKU-UHFFFAOYSA-N 0.000 claims description 3
- 238000009109 curative therapy Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- KJCZRQYWTCTIJX-UHFFFAOYSA-N CCNCC.CCNCC.CC(C)SP(O)O Chemical compound CCNCC.CCNCC.CC(C)SP(O)O KJCZRQYWTCTIJX-UHFFFAOYSA-N 0.000 claims description 2
- MPXZUWJOAXCGLF-UHFFFAOYSA-N CCNCC.CCNCC.CCNCC.CC(CO)P(O)(O)S Chemical compound CCNCC.CCNCC.CCNCC.CC(CO)P(O)(O)S MPXZUWJOAXCGLF-UHFFFAOYSA-N 0.000 claims description 2
- ZWJUENLCKCRQEB-UHFFFAOYSA-N CCSP(O)O.N.N Chemical compound CCSP(O)O.N.N ZWJUENLCKCRQEB-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- HFAXJARKRJNZBV-UHFFFAOYSA-N P(SCC)([O-])[O-].[Ca+2] Chemical compound P(SCC)([O-])[O-].[Ca+2] HFAXJARKRJNZBV-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- KPQGFNDKTRFTLX-UHFFFAOYSA-N barium(2+) dioxido(sulfido)phosphane Chemical compound P([S-])([O-])[O-].[Ba+2].P([S-])([O-])[O-].[Ba+2].[Ba+2] KPQGFNDKTRFTLX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000011575 calcium Substances 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- 238000012360 testing method Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 13
- 239000011777 magnesium Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 3
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- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- MNVKBJFKKJDBGR-UHFFFAOYSA-N butylsulfanylphosphonous acid Chemical class CCCCSP(O)O MNVKBJFKKJDBGR-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- OKKJLVBELUTLKV-MICDWDOJSA-N deuteriomethanol Chemical compound [2H]CO OKKJLVBELUTLKV-MICDWDOJSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- RJODUASCKGDMQK-UHFFFAOYSA-N diethoxy(sulfanylidene)phosphanium Chemical compound CCO[P+](=S)OCC RJODUASCKGDMQK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical class C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 description 1
- PFPGYRCCFPKXEL-UHFFFAOYSA-N disodium 2-dioxidophosphanylsulfanylpropan-1-ol Chemical compound P(SC(CO)C)([O-])[O-].[Na+].[Na+] PFPGYRCCFPKXEL-UHFFFAOYSA-N 0.000 description 1
- UYDYBRSVOLEGMP-UHFFFAOYSA-N disodium dioxido(propan-2-ylsulfanyl)phosphane Chemical compound P(SC(C)C)([O-])[O-].[Na+].[Na+] UYDYBRSVOLEGMP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical class C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- LLWDULGXUFLRGH-UHFFFAOYSA-N propan-2-yloxy(propan-2-ylsulfanyl)phosphinous acid Chemical compound CC(C)OP(O)SC(C)C LLWDULGXUFLRGH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- HNSYHCVBZGSRGQ-UHFFFAOYSA-N tripotassium dioxido(sulfido)phosphane Chemical compound P([S-])([O-])[O-].[K+].[K+].[K+] HNSYHCVBZGSRGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 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
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/201—Esters of thiophosphorus acids
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7508642A FR2303476A1 (fr) | 1975-03-14 | 1975-03-14 | Composition fongicide a base de thiophosphites |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2606761A1 DE2606761A1 (de) | 1976-09-23 |
| DE2606761C2 true DE2606761C2 (de) | 1984-05-03 |
Family
ID=9152798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2606761A Expired DE2606761C2 (de) | 1975-03-14 | 1976-02-19 | Monoester der thiophosphorigen Säure, Verfahren zu ihrer Herstellung und von Metallthiophosphiten sowie fungicide Zusammensetzungen und Verwendung der letzteren |
Country Status (25)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6021553B2 (ja) * | 1979-09-14 | 1985-05-28 | 三菱マテリアル株式会社 | 白色導電性被覆粉末およびその製造法 |
-
1975
- 1975-03-14 FR FR7508642A patent/FR2303476A1/fr active Granted
-
1976
- 1976-02-19 DE DE2606761A patent/DE2606761C2/de not_active Expired
- 1976-03-05 NL NLAANVRAGE7602309,A patent/NL183889C/xx not_active IP Right Cessation
- 1976-03-11 CS CS761595A patent/CS193066B2/cs unknown
- 1976-03-11 CS CS77458A patent/CS193082B2/cs unknown
- 1976-03-12 BG BG7600032598A patent/BG24938A3/xx unknown
- 1976-03-12 SU SU762333104A patent/SU651649A3/ru active
- 1976-03-12 PH PH18206A patent/PH14304A/en unknown
- 1976-03-12 AU AU11919/76A patent/AU507474B2/en not_active Expired
- 1976-03-12 AR AR262536A patent/AR228418A1/es active
- 1976-03-12 ES ES446025A patent/ES446025A1/es not_active Expired
- 1976-03-12 GB GB9986/76A patent/GB1525339A/en not_active Expired
- 1976-03-12 HU HU76PI509A patent/HU177025B/hu unknown
- 1976-03-12 IL IL49203A patent/IL49203A/xx unknown
- 1976-03-12 BE BE165119A patent/BE839514A/xx not_active IP Right Cessation
- 1976-03-12 ZA ZA761522A patent/ZA761522B/xx unknown
- 1976-03-12 BR BR7601525A patent/BR7601525A/pt unknown
- 1976-03-12 DD DD191815A patent/DD125771A5/xx unknown
- 1976-03-12 CH CH312476A patent/CH610185A5/xx not_active IP Right Cessation
- 1976-03-12 BG BG7600033550A patent/BG24944A3/xx not_active Expired
- 1976-03-12 PT PT64902A patent/PT64902B/pt unknown
- 1976-03-12 CA CA247,826A patent/CA1086644A/en not_active Expired
- 1976-03-13 PL PL1976200283A patent/PL101317B1/pl unknown
- 1976-03-13 JP JP51027599A patent/JPS51128435A/ja active Granted
- 1976-03-13 GR GR50298A patent/GR60033B/el unknown
- 1976-03-13 OA OA55765A patent/OA05271A/xx unknown
- 1976-03-13 PL PL1976187915A patent/PL99758B1/pl unknown
- 1976-03-15 IT IT48579/76A patent/IT1058002B/it active
-
1984
- 1984-07-05 JP JP59140407A patent/JPS6069086A/ja active Granted
-
1985
- 1985-05-28 JP JP11517985A patent/JPS6133191A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |