DE2219461C2 - Mittel zur Bekämpfung von Fungusinfektionen und einige Salze von 1,8-Diguanidino-octan - Google Patents
Mittel zur Bekämpfung von Fungusinfektionen und einige Salze von 1,8-Diguanidino-octanInfo
- Publication number
- DE2219461C2 DE2219461C2 DE2219461A DE2219461A DE2219461C2 DE 2219461 C2 DE2219461 C2 DE 2219461C2 DE 2219461 A DE2219461 A DE 2219461A DE 2219461 A DE2219461 A DE 2219461A DE 2219461 C2 DE2219461 C2 DE 2219461C2
- Authority
- DE
- Germany
- Prior art keywords
- diguanidino
- octane
- salts
- compounds
- ppm
- 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
- 208000031888 Mycoses Diseases 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title description 27
- VUUYNASTGNDRSQ-UHFFFAOYSA-N 2-[8-(diaminomethylideneamino)octyl]guanidine Chemical class NC(N)=NCCCCCCCCN=C(N)N VUUYNASTGNDRSQ-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000007787 solid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 239000003795 chemical substances by application 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000011814 protection agent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- -1 dibenzoates Chemical class 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940066528 trichloroacetate Drugs 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241001459558 Monographella nivalis Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 231100001184 nonphytotoxic Toxicity 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 241001065413 Botrytis fabae Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000223194 Fusarium culmorum Species 0.000 description 2
- 241001149475 Gaeumannomyces graminis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 235000002098 Vicia faba var. major Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229940089960 chloroacetate Drugs 0.000 description 2
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical class OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 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 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WBLYUCKTWSGGBI-UHFFFAOYSA-N 2-[6-(diaminomethylideneamino)hexyl]guanidine Chemical compound NC(N)=NCCCCCCN=C(N)N WBLYUCKTWSGGBI-UHFFFAOYSA-N 0.000 description 1
- VEVQAJFKDIJMQJ-UHFFFAOYSA-N 2-[8-(diaminomethylideneamino)octyl]guanidine;dihydrochloride Chemical compound [Cl-].[Cl-].NC([NH3+])=NCCCCCCCCN=C(N)[NH3+] VEVQAJFKDIJMQJ-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- YIDMFHBXIHLCEI-UHFFFAOYSA-N C(O)(O)=O.C(C)(=O)O.S(=O)(=O)(O)O Chemical compound C(O)(O)=O.C(C)(=O)O.S(=O)(=O)(O)O YIDMFHBXIHLCEI-UHFFFAOYSA-N 0.000 description 1
- FCCGQIAZFRFRAT-UHFFFAOYSA-N C(O)(O)=O.N(C(=N)N)CCCCCCCCNC(=N)N Chemical compound C(O)(O)=O.N(C(=N)N)CCCCCCCCNC(=N)N FCCGQIAZFRFRAT-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000975369 Phoma betae Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000544594 Uromyces viciae-fabae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- NROMIIREHKSQRR-UHFFFAOYSA-N diaminomethylidene-[8-(diaminomethylideneazaniumyl)octyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.NC(=[NH2+])NCCCCCCCCNC(N)=[NH2+] NROMIIREHKSQRR-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1056771A GB1384706A (en) | 1971-04-21 | 1971-04-21 | Pesticides |
| GB1056772 | 1972-03-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2219461A1 DE2219461A1 (de) | 1972-11-02 |
| DE2219461C2 true DE2219461C2 (de) | 1986-12-04 |
Family
ID=26247609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2219461A Expired DE2219461C2 (de) | 1971-04-21 | 1972-04-20 | Mittel zur Bekämpfung von Fungusinfektionen und einige Salze von 1,8-Diguanidino-octan |
Country Status (19)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009060249B4 (de) | 2009-12-23 | 2013-09-12 | Vladimir Lipovich | Verfahren zur Herstellung des Desinfektionsmittels Polyhexamethylenguanidinhydroiodid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6568736D0 (pt) * | 1964-04-09 | 1973-08-14 | Drug Inc Sterling | Processo para preparar uma bisguanida |
-
1972
- 1972-04-18 IL IL39245A patent/IL39245A/en unknown
- 1972-04-19 DD DD162416A patent/DD104698A1/xx unknown
- 1972-04-20 ZA ZA722685A patent/ZA722685B/xx unknown
- 1972-04-20 PH PH13473A patent/PH9938A/en unknown
- 1972-04-20 ES ES401936A patent/ES401936A1/es not_active Expired
- 1972-04-20 BR BR2456/72A patent/BR7202456D0/pt unknown
- 1972-04-20 SE SE7205200A patent/SE394851B/xx unknown
- 1972-04-20 FR FR7213926A patent/FR2133929A1/fr active Granted
- 1972-04-20 FI FI1120/72A patent/FI55751C/fi active
- 1972-04-20 NL NLAANVRAGE7205315,A patent/NL175876C/xx active Search and Examination
- 1972-04-20 CH CH586372A patent/CH559004A5/xx not_active IP Right Cessation
- 1972-04-20 AU AU41376/72A patent/AU455354B2/en not_active Expired
- 1972-04-20 SU SU721776601A patent/SU847893A3/ru active
- 1972-04-20 AT AT348072A patent/AT315575B/de active
- 1972-04-20 DE DE2219461A patent/DE2219461C2/de not_active Expired
- 1972-04-20 JP JP3923372A patent/JPS5529965B1/ja active Pending
- 1972-04-20 CA CA140,098A patent/CA991542A/en not_active Expired
- 1972-04-20 PL PL1972154869A patent/PL84494B1/pl unknown
- 1972-04-20 IT IT49764/72A patent/IT960787B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| AU455354B2 (en) | 1974-11-21 |
| FR2133929A1 (en) | 1972-12-01 |
| FR2133929B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-24 |
| PH9938A (en) | 1976-06-14 |
| AU4137672A (en) | 1973-10-25 |
| ZA722685B (en) | 1973-01-31 |
| AT315575B (de) | 1974-05-27 |
| SU847893A3 (ru) | 1981-07-15 |
| PL84494B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-30 |
| NL175876C (nl) | 1985-01-16 |
| DE2219461A1 (de) | 1972-11-02 |
| FI55751C (fi) | 1979-10-10 |
| ES401936A1 (es) | 1975-10-16 |
| IT960787B (it) | 1973-11-30 |
| SE394851B (sv) | 1977-07-18 |
| CA991542A (en) | 1976-06-22 |
| DD104698A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-20 |
| IL39245A (en) | 1974-12-31 |
| JPS5529965B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-08-07 |
| FI55751B (fi) | 1979-06-29 |
| NL7205315A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-24 |
| BR7202456D0 (pt) | 1974-01-17 |
| CH559004A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-28 |
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