DE2654282C2 - Carbamatsulfenylcarbamoylfluorid-Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Pestizide - Google Patents
Carbamatsulfenylcarbamoylfluorid-Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende PestizideInfo
- Publication number
- DE2654282C2 DE2654282C2 DE2654282A DE2654282A DE2654282C2 DE 2654282 C2 DE2654282 C2 DE 2654282C2 DE 2654282 A DE2654282 A DE 2654282A DE 2654282 A DE2654282 A DE 2654282A DE 2654282 C2 DE2654282 C2 DE 2654282C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- carbamate
- carbon atoms
- preparation
- plants
- 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
- QPSCUSPCOVXELC-UHFFFAOYSA-N carbamic acid;n-sulfanylidenecarbamoyl fluoride Chemical class NC(O)=O.FC(=O)N=S QPSCUSPCOVXELC-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 19
- 238000000034 method Methods 0.000 title description 15
- 239000000575 pesticide Substances 0.000 title description 5
- -1 alkyl radicals Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 50
- 238000012360 testing method Methods 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000725 suspension Substances 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- DCAMNZNIQSVBSR-UHFFFAOYSA-N n-[carbonofluoridoyl(methyl)amino]sulfanyl-n-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SN(C)C(F)=O DCAMNZNIQSVBSR-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000005507 spraying Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 150000002923 oximes Chemical class 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 5
- 239000005916 Methomyl Substances 0.000 description 5
- 241001674048 Phthiraptera Species 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
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- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001069 nematicidal effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 206010004966 Bite Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- JPSHMDUAFDEKAR-UHFFFAOYSA-N n-(1,4-dithian-2-ylidene)hydroxylamine Chemical compound ON=C1CSCCS1 JPSHMDUAFDEKAR-UHFFFAOYSA-N 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- CIAKIXNUPLNVMO-UHFFFAOYSA-N (propanoylamino) thiohypochlorite Chemical compound CCC(=O)NSCl CIAKIXNUPLNVMO-UHFFFAOYSA-N 0.000 description 1
- IGOWHGRNPLFNDJ-ZPHPHTNESA-N (z)-9-tricosene Chemical compound CCCCCCCCCCCCC\C=C/CCCCCCCC IGOWHGRNPLFNDJ-ZPHPHTNESA-N 0.000 description 1
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 1
- ILQHJFNAUDYXON-UHFFFAOYSA-N 2-hydroxyimino-3,5,5-trimethyl-1,3-thiazolidin-4-one Chemical compound CN1C(=NO)SC(C)(C)C1=O ILQHJFNAUDYXON-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- ZFGMCJAXIZTVJA-UHFFFAOYSA-N 2-methyl-2-(methylsulfanyl)propanal oxime Chemical compound CSC(C)(C)C=NO ZFGMCJAXIZTVJA-UHFFFAOYSA-N 0.000 description 1
- XSFWCIBEJZADAF-UHFFFAOYSA-N 2-prop-2-ynoxyphenol Chemical compound OC1=CC=CC=C1OCC#C XSFWCIBEJZADAF-UHFFFAOYSA-N 0.000 description 1
- OIHIYRYYEMJNPB-UHFFFAOYSA-N 3,6-dihydrodithiine Chemical compound C1SSCC=C1 OIHIYRYYEMJNPB-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/636,629 US4338450A (en) | 1975-12-01 | 1975-12-01 | Carbamate-sulfenyl-carbamoyl fluoride compounds |
| US73721976A | 1976-11-04 | 1976-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2654282A1 DE2654282A1 (de) | 1977-06-08 |
| DE2654282C2 true DE2654282C2 (de) | 1984-05-24 |
Family
ID=27092659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2654282A Expired DE2654282C2 (de) | 1975-12-01 | 1976-11-30 | Carbamatsulfenylcarbamoylfluorid-Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Pestizide |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS594429B2 (enExample) |
| AT (1) | AT353803B (enExample) |
| AU (1) | AU515667B2 (enExample) |
| BR (1) | BR7607998A (enExample) |
| CA (1) | CA1069127A (enExample) |
| CH (2) | CH620425A5 (enExample) |
| DE (1) | DE2654282C2 (enExample) |
| DK (1) | DK538276A (enExample) |
| ES (1) | ES468281A1 (enExample) |
| FR (1) | FR2333791A1 (enExample) |
| GB (1) | GB1512910A (enExample) |
| IL (1) | IL51000A (enExample) |
| IT (1) | IT1070073B (enExample) |
| NL (1) | NL7613334A (enExample) |
| SE (1) | SE7612479L (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234580A (en) * | 1977-03-28 | 1980-11-18 | Union Carbide Corporation | Carbamate thiosulfenylcarbamoyl fluoride compounds |
| US4225615A (en) * | 1978-04-24 | 1980-09-30 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4268520A (en) | 1978-04-24 | 1981-05-19 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4127605A (en) * | 1978-04-24 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Substituted carbamate intermediate |
| DE2828133A1 (de) * | 1978-06-27 | 1980-01-10 | Bayer Ag | N-sulfenylierte carbamoyloximino-1- methylthio-butane, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| US4291054A (en) * | 1979-12-10 | 1981-09-22 | E. I. Du Pont De Nemours And Company | Insecticidal carbamoyl sulfides |
| US4511578A (en) * | 1982-03-31 | 1985-04-16 | Ciba-Geigy Corporation | Acyclamidosulfenylcarbamates for controlling insects |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254359A1 (de) * | 1972-11-07 | 1974-05-16 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1976
- 1976-11-09 SE SE7612479A patent/SE7612479L/xx not_active Application Discontinuation
- 1976-11-26 IL IL51000A patent/IL51000A/xx unknown
- 1976-11-29 CA CA266,788A patent/CA1069127A/en not_active Expired
- 1976-11-29 AU AU20066/76A patent/AU515667B2/en not_active Expired
- 1976-11-30 DK DK538276A patent/DK538276A/da unknown
- 1976-11-30 FR FR7636132A patent/FR2333791A1/fr active Granted
- 1976-11-30 DE DE2654282A patent/DE2654282C2/de not_active Expired
- 1976-11-30 NL NL7613334A patent/NL7613334A/xx active Search and Examination
- 1976-11-30 CH CH1506076A patent/CH620425A5/fr not_active IP Right Cessation
- 1976-11-30 BR BR7607998A patent/BR7607998A/pt unknown
- 1976-11-30 GB GB49848/76A patent/GB1512910A/en not_active Expired
- 1976-11-30 AT AT884976A patent/AT353803B/de not_active IP Right Cessation
- 1976-11-30 JP JP51143049A patent/JPS594429B2/ja not_active Expired
- 1976-11-30 IT IT69862/76A patent/IT1070073B/it active
-
1978
- 1978-03-28 ES ES468281A patent/ES468281A1/es not_active Expired
-
1979
- 1979-11-27 CH CH1053779A patent/CH623034A5/fr not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285106A (en) | 1977-07-15 |
| CH623034A5 (en) | 1981-05-15 |
| BR7607998A (pt) | 1977-11-08 |
| AT353803B (de) | 1979-12-10 |
| ES468281A1 (es) | 1978-11-16 |
| IL51000A (en) | 1981-11-30 |
| SE7612479L (sv) | 1977-06-02 |
| IT1070073B (it) | 1985-03-25 |
| CH620425A5 (en) | 1980-11-28 |
| FR2333791B1 (enExample) | 1981-01-09 |
| AU2006676A (en) | 1978-06-08 |
| CA1069127A (en) | 1980-01-01 |
| FR2333791A1 (fr) | 1977-07-01 |
| AU515667B2 (en) | 1981-04-16 |
| GB1512910A (en) | 1978-06-01 |
| DK538276A (da) | 1977-06-02 |
| IL51000A0 (en) | 1977-01-31 |
| ATA884976A (de) | 1979-05-15 |
| NL7613334A (nl) | 1977-06-03 |
| DE2654282A1 (de) | 1977-06-08 |
| JPS594429B2 (ja) | 1984-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |