DE1695579A1 - Thiocyanoindolderivate - Google Patents
ThiocyanoindolderivateInfo
- Publication number
- DE1695579A1 DE1695579A1 DE19681695579 DE1695579A DE1695579A1 DE 1695579 A1 DE1695579 A1 DE 1695579A1 DE 19681695579 DE19681695579 DE 19681695579 DE 1695579 A DE1695579 A DE 1695579A DE 1695579 A1 DE1695579 A1 DE 1695579A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- thiocyanoindole
- aryl
- group
- aralkyl
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- -1 aralkyi Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004001 thioalkyl group Chemical group 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 244000005700 microbiome Species 0.000 claims description 11
- 239000003973 paint Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000002270 dispersing agent Substances 0.000 claims description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 230000009931 harmful effect Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000003701 inert diluent Substances 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- FFZKPUKPFSCMCP-UHFFFAOYSA-N (7-chloro-1H-indol-3-yl) thiocyanate Chemical compound ClC=1C=CC=C2C(=CNC12)SC#N FFZKPUKPFSCMCP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- KCDLVLXPGIVCAU-UHFFFAOYSA-N (1-acetylindol-3-yl) thiocyanate Chemical compound C1=CC=C2N(C(=O)C)C=C(SC#N)C2=C1 KCDLVLXPGIVCAU-UHFFFAOYSA-N 0.000 claims 1
- LZMRCLCRCPVUAZ-UHFFFAOYSA-N (6-chloro-1H-indol-3-yl) thiocyanate Chemical compound ClC1=CC=C2C(=CNC2=C1)SC#N LZMRCLCRCPVUAZ-UHFFFAOYSA-N 0.000 claims 1
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 13
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 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 5
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 5
- 229940116357 potassium thiocyanate Drugs 0.000 description 5
- UUVFLDAVBAEABK-UHFFFAOYSA-N 1h-indol-3-yl thiocyanate Chemical compound C1=CC=C2C(SC#N)=CNC2=C1 UUVFLDAVBAEABK-UHFFFAOYSA-N 0.000 description 4
- 241000223678 Aureobasidium pullulans Species 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 229920001131 Pulp (paper) Polymers 0.000 description 3
- 241000180287 Rhizina undulata Species 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- ZZOPTTFOLGWOEK-UHFFFAOYSA-N 1H-indol-2-yl thiocyanate Chemical compound C1=CC=C2NC(SC#N)=CC2=C1 ZZOPTTFOLGWOEK-UHFFFAOYSA-N 0.000 description 2
- OXTXMDMNXBFLLL-UHFFFAOYSA-N 1H-indol-5-yl thiocyanate Chemical compound N#CSc1ccc2[nH]ccc2c1 OXTXMDMNXBFLLL-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- 241000094558 Antrodia sinuosa Species 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000122692 Fusarium avenaceum Species 0.000 description 2
- 241000593551 Gremmeniella abietina Species 0.000 description 2
- 241000190090 Herpotrichia Species 0.000 description 2
- 241000588915 Klebsiella aerogenes Species 0.000 description 2
- 244000162269 Lentinus lepideus Species 0.000 description 2
- 235000017066 Lentinus lepideus Nutrition 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000222640 Polyporus Species 0.000 description 2
- 241000222355 Trametes versicolor Species 0.000 description 2
- 241000223261 Trichoderma viride Species 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229940100892 mercury compound Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- GSNGESLUAXSQIS-UHFFFAOYSA-N (1-butylindol-3-yl) thiocyanate Chemical compound C(CCC)N1C=C(C2=CC=CC=C12)SC#N GSNGESLUAXSQIS-UHFFFAOYSA-N 0.000 description 1
- YJXBUBLBWMUGPJ-UHFFFAOYSA-N (1-methylindol-3-yl) thiocyanate Chemical compound C1=CC=C2N(C)C=C(SC#N)C2=C1 YJXBUBLBWMUGPJ-UHFFFAOYSA-N 0.000 description 1
- XVKBHABWWUDDBD-UHFFFAOYSA-N (4-chloro-1H-indol-3-yl) thiocyanate Chemical compound ClC1=C2C(=CNC2=CC=C1)SC#N XVKBHABWWUDDBD-UHFFFAOYSA-N 0.000 description 1
- QRKKTXWUDLJYCV-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)(Cl)C(=O)C(F)(F)Cl QRKKTXWUDLJYCV-UHFFFAOYSA-N 0.000 description 1
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- QJRWYBIKLXNYLF-UHFFFAOYSA-N 6-methoxy-1h-indole Chemical compound COC1=CC=C2C=CNC2=C1 QJRWYBIKLXNYLF-UHFFFAOYSA-N 0.000 description 1
- WMYQAKANKREQLM-UHFFFAOYSA-N 7-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1NC=C2 WMYQAKANKREQLM-UHFFFAOYSA-N 0.000 description 1
- 241000218642 Abies Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241001600095 Coniophora puteana Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001474354 Flavobacterium marinum Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 241000735439 Heterobasidion annosum Species 0.000 description 1
- 241000318230 Merulius Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000235400 Phycomyces Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001674251 Serpula lacrymans Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000222646 Stereum Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- NRMXZJVDGLYURI-UHFFFAOYSA-N mercury(1+);methanolate Chemical compound CO[Hg] NRMXZJVDGLYURI-UHFFFAOYSA-N 0.000 description 1
- 238000012009 microbiological test Methods 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000015047 pilsener Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000167 toxic agent Toxicity 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
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NRINZBKAERVHFW-UHFFFAOYSA-L zinc;dicarbamate Chemical compound [Zn+2].NC([O-])=O.NC([O-])=O NRINZBKAERVHFW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Closures For Containers (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE00193/67A SE347422B (https=) | 1967-01-04 | 1967-01-04 | |
| SE772267 | 1967-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695579A1 true DE1695579A1 (de) | 1971-04-22 |
Family
ID=26654127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681695579 Pending DE1695579A1 (de) | 1967-01-04 | 1968-01-03 | Thiocyanoindolderivate |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US3546244A (https=) |
| DE (1) | DE1695579A1 (https=) |
| FI (1) | FI50036C (https=) |
| GB (1) | GB1215631A (https=) |
| NO (1) | NO125758B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3533856A1 (de) * | 1985-09-23 | 1987-05-21 | Wilhelm Koenig | Vorrichtung zur herstellung von hartdisketten aus glas |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3925304A (en) * | 1972-11-20 | 1975-12-09 | Tenneco Chem | Surface-coating compositions containing n-(indazolyl-n' 1'-methyl)dialkanolamines |
| CN119823020A (zh) * | 2025-01-10 | 2025-04-15 | 常州工程职业技术学院 | 一种3-硫氰基吲哚衍生物的制备方法 |
-
1968
- 1968-01-01 GB GB61/68A patent/GB1215631A/en not_active Expired
- 1968-01-02 NO NO0012/68A patent/NO125758B/no unknown
- 1968-01-03 US US695352A patent/US3546244A/en not_active Expired - Lifetime
- 1968-01-03 DE DE19681695579 patent/DE1695579A1/de active Pending
- 1968-01-04 FI FI680021A patent/FI50036C/fi active
-
1970
- 1970-06-08 US US44602A patent/US3646210A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3533856A1 (de) * | 1985-09-23 | 1987-05-21 | Wilhelm Koenig | Vorrichtung zur herstellung von hartdisketten aus glas |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1215631A (en) | 1970-12-16 |
| FI50036C (fi) | 1975-12-10 |
| US3646210A (en) | 1972-02-29 |
| US3546244A (en) | 1970-12-08 |
| NO125758B (https=) | 1972-10-30 |
| FI50036B (https=) | 1975-09-01 |
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