DE2017969A1 - 2-Arylimino-thiazolidine und Verfahren zu ihrer Herstellung - Google Patents
2-Arylimino-thiazolidine und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2017969A1 DE2017969A1 DE19702017969 DE2017969A DE2017969A1 DE 2017969 A1 DE2017969 A1 DE 2017969A1 DE 19702017969 DE19702017969 DE 19702017969 DE 2017969 A DE2017969 A DE 2017969A DE 2017969 A1 DE2017969 A1 DE 2017969A1
- Authority
- DE
- Germany
- Prior art keywords
- thiazolidine
- butyl
- chloro
- general formula
- thiazolidines
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000003585 thioureas Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 244000078703 ectoparasite Species 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 230000001984 ectoparasiticidal effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 241000282979 Alces alces Species 0.000 claims 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 claims 1
- 240000002834 Paulownia tomentosa Species 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- -1 2-trifluoromethylphenyl Chemical group 0.000 description 171
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 241000238876 Acari Species 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 150000002540 isothiocyanates Chemical class 0.000 description 10
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 3
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- JYKYYPPZLPVIBY-UHFFFAOYSA-N 1-isothiocyanato-2-methylbenzene Chemical compound CC1=CC=CC=C1N=C=S JYKYYPPZLPVIBY-UHFFFAOYSA-N 0.000 description 2
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XEFWQBVAONCITR-UHFFFAOYSA-N 3-butyl-N-(2,6-dimethylphenyl)-1,3-thiazolidin-2-imine Chemical compound C1(=C(C=CC=C1C)C)N=C1SCCN1CCCC XEFWQBVAONCITR-UHFFFAOYSA-N 0.000 description 2
- PXFZGFFPEMYMHS-UHFFFAOYSA-N 3-methyl-N-[2-(trifluoromethyl)phenyl]-1,3-thiazolidin-2-imine Chemical compound FC(C1=C(C=CC=C1)N=C1SCCN1C)(F)F PXFZGFFPEMYMHS-UHFFFAOYSA-N 0.000 description 2
- ZWIUYICQCSGIDO-UHFFFAOYSA-N 3-methyl-n-(2-methylphenyl)-1,3-thiazolidin-2-imine Chemical compound CN1CCSC1=NC1=CC=CC=C1C ZWIUYICQCSGIDO-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- TXZJFANBUMPZFI-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-3-propan-2-yl-1,3-thiazolidin-2-imine Chemical compound C1(=C(C=CC=C1C)C)N=C1SCCN1C(C)C TXZJFANBUMPZFI-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 150000002169 ethanolamines Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- FLONNULSKGBJKL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)carbamothioyl chloride Chemical compound ClC(=S)NC1=C(Cl)C=CC=C1Cl FLONNULSKGBJKL-UHFFFAOYSA-N 0.000 description 2
- NDXGPWJLIYHETN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-methyl-1,3-thiazolidin-2-imine Chemical compound CN1CCSC1=NC1=CC=CC=C1Cl NDXGPWJLIYHETN-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
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- 238000007363 ring formation reaction Methods 0.000 description 2
- URUQZMBSURPJJV-NSCUHMNNSA-N (e)-n-(2-hydroxyethyl)but-2-enamide Chemical compound C\C=C\C(=O)NCCO URUQZMBSURPJJV-NSCUHMNNSA-N 0.000 description 1
- BOOIWYNDUXYILL-UHFFFAOYSA-N (±)-2-butylthiazolidine Chemical compound CCCCC1NCCS1 BOOIWYNDUXYILL-UHFFFAOYSA-N 0.000 description 1
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
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- HABDCZIEPQRQMT-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC=CC=C1Cl HABDCZIEPQRQMT-UHFFFAOYSA-N 0.000 description 1
- MMGAZMPMTULANE-UHFFFAOYSA-N 1-chloro-2-isothiocyanato-3-methoxybenzene Chemical compound ClC1=C(C(=CC=C1)OC)N=C=S MMGAZMPMTULANE-UHFFFAOYSA-N 0.000 description 1
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- JBDOSUUXMYMWQH-UHFFFAOYSA-N 1-naphthyl isothiocyanate Chemical compound C1=CC=C2C(N=C=S)=CC=CC2=C1 JBDOSUUXMYMWQH-UHFFFAOYSA-N 0.000 description 1
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- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- WCEKYBFYVKLEAM-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-3-methyl-1,3-thiazolidin-2-imine Chemical compound CN1CCSC1=NC1=C(C)C=CC=C1Cl WCEKYBFYVKLEAM-UHFFFAOYSA-N 0.000 description 1
- UNHQZBAKHUKRFS-UHFFFAOYSA-N n-(2-chloroethyl)-2-methylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)(C)NCCCl UNHQZBAKHUKRFS-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017969 DE2017969A1 (de) | 1970-04-15 | 1970-04-15 | 2-Arylimino-thiazolidine und Verfahren zu ihrer Herstellung |
| CH427171A CH560505A5 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-03-24 | |
| CH1682374A CH569409A5 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-03-24 | |
| ZA712055A ZA712055B (en) | 1970-04-15 | 1971-03-30 | Arylimino-thiazolidines,processes for their preparation,and their use as acaricides |
| SE04403/71A SE369719B (enrdf_load_stackoverflow) | 1970-04-15 | 1971-04-05 | |
| NL7104980A NL7104980A (enrdf_load_stackoverflow) | 1970-04-15 | 1971-04-14 | |
| JP2320271A JPS5345365B1 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-04-14 | |
| AT333572A AT311961B (de) | 1970-04-15 | 1971-04-15 | Verfahren zur Herstellung von neuen 2-Arylimino-thiazolidinen und ihren Salzen |
| FR7113380A FR2089720A5 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-04-15 | |
| AT318671A AT306008B (de) | 1970-04-15 | 1971-04-15 | Verfahren zur Herstellung von neuen 2-Arylimino-thiazolidinen und ihren Salzen |
| AT333672A AT311962B (de) | 1970-04-15 | 1971-04-15 | Verfahren zur Herstellung von neuen 2-Arylimino-thiazolidinen und ihren Salzen |
| AT333772A AT311963B (de) | 1970-04-15 | 1971-04-15 | Verfahren zur Herstellung von neuen 2-Aryliminothiazolidinen und ihren Salzen |
| BE765801A BE765801A (fr) | 1970-04-15 | 1971-04-15 | Nouvelles 2-arylimino-thiazolidines et leur procede de preparation |
| GB2650571*A GB1341072A (en) | 1970-04-15 | 1971-04-19 | Aryliminothiazolidines processes for their preparation and their use as acaricides |
| DD173830*A DD107200A5 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-09-03 | |
| US00205348A US3804848A (en) | 1970-04-15 | 1971-12-06 | Aryliminothiazolidines |
| US418056A US3898340A (en) | 1970-04-15 | 1973-11-21 | Aryliminothiazolidine compositions and methods |
| IN1912/CAL/75A IN140425B (enrdf_load_stackoverflow) | 1970-04-15 | 1975-10-04 | |
| IN1911/CAL/1975A IN140424B (enrdf_load_stackoverflow) | 1970-04-15 | 1975-10-04 | |
| GT198064138A GT198064138A (es) | 1970-04-15 | 1980-06-25 | 2-arilimino-tiazolidinas y procedimiento para su produccion |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017969 DE2017969A1 (de) | 1970-04-15 | 1970-04-15 | 2-Arylimino-thiazolidine und Verfahren zu ihrer Herstellung |
| DD173830*A DD107200A5 (enrdf_load_stackoverflow) | 1970-04-15 | 1971-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2017969A1 true DE2017969A1 (de) | 1972-03-16 |
Family
ID=25747505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017969 Pending DE2017969A1 (de) | 1970-04-15 | 1970-04-15 | 2-Arylimino-thiazolidine und Verfahren zu ihrer Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| AT (4) | AT306008B (enrdf_load_stackoverflow) |
| BE (1) | BE765801A (enrdf_load_stackoverflow) |
| CH (2) | CH569409A5 (enrdf_load_stackoverflow) |
| DD (1) | DD107200A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2017969A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2089720A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1341072A (enrdf_load_stackoverflow) |
| NL (1) | NL7104980A (enrdf_load_stackoverflow) |
| SE (1) | SE369719B (enrdf_load_stackoverflow) |
| ZA (1) | ZA712055B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2619724A1 (de) * | 1975-05-07 | 1976-11-18 | Ciba Geigy Ag | Neue thiazoline |
-
1970
- 1970-04-15 DE DE19702017969 patent/DE2017969A1/de active Pending
-
1971
- 1971-03-24 CH CH1682374A patent/CH569409A5/xx not_active IP Right Cessation
- 1971-03-24 CH CH427171A patent/CH560505A5/xx not_active IP Right Cessation
- 1971-03-30 ZA ZA712055A patent/ZA712055B/xx unknown
- 1971-04-05 SE SE04403/71A patent/SE369719B/xx unknown
- 1971-04-14 NL NL7104980A patent/NL7104980A/xx unknown
- 1971-04-15 FR FR7113380A patent/FR2089720A5/fr not_active Expired
- 1971-04-15 AT AT318671A patent/AT306008B/de not_active IP Right Cessation
- 1971-04-15 AT AT333672A patent/AT311962B/de not_active IP Right Cessation
- 1971-04-15 BE BE765801A patent/BE765801A/xx unknown
- 1971-04-15 AT AT333772A patent/AT311963B/de not_active IP Right Cessation
- 1971-04-15 AT AT333572A patent/AT311961B/de not_active IP Right Cessation
- 1971-04-19 GB GB2650571*A patent/GB1341072A/en not_active Expired
- 1971-09-03 DD DD173830*A patent/DD107200A5/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2619724A1 (de) * | 1975-05-07 | 1976-11-18 | Ciba Geigy Ag | Neue thiazoline |
Also Published As
| Publication number | Publication date |
|---|---|
| BE765801A (fr) | 1971-10-15 |
| AT311961B (de) | 1973-12-10 |
| GB1341072A (en) | 1973-12-19 |
| DD107200A5 (enrdf_load_stackoverflow) | 1974-07-20 |
| ZA712055B (en) | 1971-12-29 |
| NL7104980A (enrdf_load_stackoverflow) | 1971-10-19 |
| AT306008B (de) | 1973-03-26 |
| FR2089720A5 (enrdf_load_stackoverflow) | 1972-01-07 |
| AT311963B (de) | 1973-12-10 |
| SE369719B (enrdf_load_stackoverflow) | 1974-09-16 |
| AT311962B (de) | 1973-12-10 |
| CH560505A5 (enrdf_load_stackoverflow) | 1975-04-15 |
| CH569409A5 (enrdf_load_stackoverflow) | 1975-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |