DE2051498C3 - Thiophosphorsaure O,S diester monoamide und ihre Verwendung als Pestizide - Google Patents
Thiophosphorsaure O,S diester monoamide und ihre Verwendung als PestizideInfo
- Publication number
- DE2051498C3 DE2051498C3 DE2051498A DE2051498A DE2051498C3 DE 2051498 C3 DE2051498 C3 DE 2051498C3 DE 2051498 A DE2051498 A DE 2051498A DE 2051498 A DE2051498 A DE 2051498A DE 2051498 C3 DE2051498 C3 DE 2051498C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- thiophosphoric acid
- acid ester
- mixture
- hours
- 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000575 pesticide Substances 0.000 title claims description 4
- 150000005690 diesters Chemical class 0.000 title description 2
- 229910052760 oxygen Inorganic materials 0.000 title description 2
- 229910052717 sulfur Inorganic materials 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 isobutenyl Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003186 propargylic group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- 241000209094 Oryza Species 0.000 description 9
- 241001454295 Tetranychidae Species 0.000 description 9
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 238000007865 diluting Methods 0.000 description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BOKOVLFWCAFYHP-UHFFFAOYSA-N dihydroxy-methoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(O)(O)=S BOKOVLFWCAFYHP-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
- OJZGWRZUOHSWMB-UHFFFAOYSA-N ethoxy-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(O)(O)=S OJZGWRZUOHSWMB-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 4
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- DXVVRJYUCBYYFN-UHFFFAOYSA-N COP(O)(O)=[S+]CC#C Chemical compound COP(O)(O)=[S+]CC#C DXVVRJYUCBYYFN-UHFFFAOYSA-N 0.000 description 3
- 241000254137 Cicadidae Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- YMFWYDYJHRGGPF-UHFFFAOYSA-N 2,3-dibromoprop-1-ene Chemical compound BrCC(Br)=C YMFWYDYJHRGGPF-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- CKKMHKOPHRMNMQ-UHFFFAOYSA-N CCOP(O)(O)=[S+]CC#C Chemical compound CCOP(O)(O)=[S+]CC#C CKKMHKOPHRMNMQ-UHFFFAOYSA-N 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000010152 pollination Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WLIADPFXSACYLS-RQOWECAXSA-N (z)-1,3-dichlorobut-2-ene Chemical compound C\C(Cl)=C\CCl WLIADPFXSACYLS-RQOWECAXSA-N 0.000 description 1
- YTKRILODNOEEPX-UHFFFAOYSA-N 1-chlorobut-2-ene Chemical compound CC=CCCl YTKRILODNOEEPX-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- HJCTVUWPHAZTLI-UHFFFAOYSA-N 2-ethylsulfanylethanamine Chemical compound CCSCCN HJCTVUWPHAZTLI-UHFFFAOYSA-N 0.000 description 1
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 1
- VRTNIWBNFSHDEB-UHFFFAOYSA-N 3,3-dichloroprop-1-ene Chemical compound ClC(Cl)C=C VRTNIWBNFSHDEB-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- VZGLVCFVUREVDP-UHFFFAOYSA-N 3-chlorobut-1-ene Chemical compound CC(Cl)C=C VZGLVCFVUREVDP-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XZFJXVZHIGMRJH-UHFFFAOYSA-N CCC[S+]=P(O)(O)OCC Chemical compound CCC[S+]=P(O)(O)OCC XZFJXVZHIGMRJH-UHFFFAOYSA-N 0.000 description 1
- YYKQEGPKGONLPV-UHFFFAOYSA-N CCOP(O)(O)=[S+]C Chemical compound CCOP(O)(O)=[S+]C YYKQEGPKGONLPV-UHFFFAOYSA-N 0.000 description 1
- IJBMJRBZFSZBJT-UHFFFAOYSA-N CC[S+]=P(O)(O)OC Chemical compound CC[S+]=P(O)(O)OC IJBMJRBZFSZBJT-UHFFFAOYSA-N 0.000 description 1
- QPQFPIORGACVMW-UHFFFAOYSA-N COP(O)(O)=[S+]CC=CCl Chemical compound COP(O)(O)=[S+]CC=CCl QPQFPIORGACVMW-UHFFFAOYSA-N 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000353522 Earias insulana Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001299253 Henosepilachna vigintioctopunctata Species 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
- 241000255777 Lepidoptera Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000669245 Unaspis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8505969A JPS54972B1 (US07655688-20100202-C00548.png) | 1969-10-23 | 1969-10-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2051498A1 DE2051498A1 (de) | 1971-05-13 |
| DE2051498B2 DE2051498B2 (de) | 1973-02-22 |
| DE2051498C3 true DE2051498C3 (de) | 1973-09-20 |
Family
ID=13848050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2051498A Expired DE2051498C3 (de) | 1969-10-23 | 1970-10-20 | Thiophosphorsaure O,S diester monoamide und ihre Verwendung als Pestizide |
Country Status (12)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454682A (en) * | 1966-01-21 | 1969-07-08 | Shell Oil Co | Phosphorodiamidothioates |
-
1969
- 1969-10-23 JP JP8505969A patent/JPS54972B1/ja active Pending
-
1970
- 1970-10-12 US US00080224A patent/US3800011A/en not_active Expired - Lifetime
- 1970-10-12 ZA ZA706946A patent/ZA706946B/xx unknown
- 1970-10-16 GB GB49253/70A patent/GB1275330A/en not_active Expired
- 1970-10-18 EG EG443/70*UA patent/EG10012A/xx active
- 1970-10-20 DE DE2051498A patent/DE2051498C3/de not_active Expired
- 1970-10-20 BR BR223197/70A patent/BR7023197D0/pt unknown
- 1970-10-22 NL NL707015472A patent/NL150118B/xx not_active IP Right Cessation
- 1970-10-22 FR FR707038155A patent/FR2065483B1/fr not_active Expired
- 1970-10-22 PL PL1970144027A patent/PL72811B1/pl unknown
- 1970-10-22 CA CA096,317A patent/CA956968A/en not_active Expired
- 1970-10-23 CH CH1571170A patent/CH542886A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US3800011A (en) | 1974-03-26 |
| CA956968A (en) | 1974-10-29 |
| DE2051498A1 (de) | 1971-05-13 |
| BR7023197D0 (pt) | 1973-02-20 |
| FR2065483B1 (US07655688-20100202-C00548.png) | 1973-01-12 |
| EG10012A (en) | 1976-01-31 |
| PL72811B1 (US07655688-20100202-C00548.png) | 1974-08-30 |
| GB1275330A (en) | 1972-05-24 |
| CH542886A (de) | 1973-10-15 |
| NL150118B (nl) | 1976-07-15 |
| FR2065483A1 (US07655688-20100202-C00548.png) | 1971-07-30 |
| JPS54972B1 (US07655688-20100202-C00548.png) | 1979-01-18 |
| NL7015472A (US07655688-20100202-C00548.png) | 1971-04-27 |
| ZA706946B (en) | 1971-07-28 |
| DE2051498B2 (de) | 1973-02-22 |
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