DE1493210C3 - - Google Patents
Info
- Publication number
- DE1493210C3 DE1493210C3 DE19651493210 DE1493210A DE1493210C3 DE 1493210 C3 DE1493210 C3 DE 1493210C3 DE 19651493210 DE19651493210 DE 19651493210 DE 1493210 A DE1493210 A DE 1493210A DE 1493210 C3 DE1493210 C3 DE 1493210C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- hexane
- formula
- compounds
- hydrochloride
- 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 150000003839 salts Chemical class 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- -1 n-octyl Chemical group 0.000 description 22
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 12
- 230000000844 anti-bacterial effect Effects 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 8
- 239000012458 free base Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229940123208 Biguanide Drugs 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 150000004283 biguanides Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- IXBPPZBJIFNGJJ-UHFFFAOYSA-N sodium;cyanoiminomethylideneazanide Chemical compound [Na+].N#C[N-]C#N IXBPPZBJIFNGJJ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- YXZZOMVBHPCKMM-UHFFFAOYSA-N 2-[6-[[amino-(cyanoamino)methylidene]amino]hexyl]-1-cyanoguanidine Chemical compound N#CNC(N)=NCCCCCCN=C(N)NC#N YXZZOMVBHPCKMM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 150000004287 bisbiguanides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CNDZQSIYCAWQDL-UHFFFAOYSA-N 2-[6-[[amino-(hexylamino)methylidene]amino]hexyl]-1-hexylguanidine Chemical compound CCCCCCNC(N)=NCCCCCCN=C(N)NCCCCCC CNDZQSIYCAWQDL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- WGFUAJNREFNKPN-UHFFFAOYSA-N 5-chlorothiadiazole-4-carboxamide Chemical compound NC(=O)C=1N=NSC=1Cl WGFUAJNREFNKPN-UHFFFAOYSA-N 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 235000002262 Lycopersicon Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000111332 Molanna albicans Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 241000718543 Ormosia krugii Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000589624 Pseudomonas amygdali pv. tabaci Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001509980 Shelfordella lateralis Species 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241001480236 Strongyloides ratti Species 0.000 description 1
- 235000009430 Thespesia populnea Nutrition 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- CKWIKVARGJVPLG-UHFFFAOYSA-N [I-].C(CCCCC)NC(SCC)=[NH2+] Chemical compound [I-].C(CCCCC)NC(SCC)=[NH2+] CKWIKVARGJVPLG-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 1
- GSNUNTMZZWSJCW-UHFFFAOYSA-N decylthiourea Chemical compound CCCCCCCCCCNC(N)=S GSNUNTMZZWSJCW-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- SRUKOJDGOUUFRB-UHFFFAOYSA-N heptylazanium;chloride Chemical compound Cl.CCCCCCCN SRUKOJDGOUUFRB-UHFFFAOYSA-N 0.000 description 1
- TWRQCVNFACGORI-UHFFFAOYSA-N hexane;dihydrochloride Chemical compound Cl.Cl.CCCCCC TWRQCVNFACGORI-UHFFFAOYSA-N 0.000 description 1
- LMYQWQCDUHNQLF-UHFFFAOYSA-N hexylthiourea Chemical compound CCCCCCNC(N)=S LMYQWQCDUHNQLF-UHFFFAOYSA-N 0.000 description 1
- PHFDTSRDEZEOHG-UHFFFAOYSA-N hydron;octan-1-amine;chloride Chemical compound Cl.CCCCCCCCN PHFDTSRDEZEOHG-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QAKUNEDFMJPMGO-UHFFFAOYSA-N octylthiourea Chemical compound CCCCCCCCNC(N)=S QAKUNEDFMJPMGO-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YPCZZGDKIBPATR-UHFFFAOYSA-N potassium dicyanoazanide Chemical compound [K+].N#C[N-]C#N YPCZZGDKIBPATR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35861464 | 1964-04-09 | ||
| DEST023662 | 1965-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493210C3 true DE1493210C3 (enrdf_load_stackoverflow) | 1976-12-02 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1493210B2 (de) | Bis-guanidine und bis-biguanide und verfahren zu deren herstellung | |
| DE69216674T2 (de) | Biguanidederivate, Verfahren zu ihrer Herstellung und diese enthaltende Desinfektionsmittel | |
| DE1668871A1 (de) | Quaternaere Ammoniumverbindungen und ihre Verwendung | |
| DE2009743A1 (de) | Substituierte Biguanide mit antihyperglykämischer Wirkung | |
| DE2944296C2 (de) | Bekämpfung von pflanzlichen Viruserkrankungen | |
| CH344404A (de) | Verfahren zur Herstellung von neuen Biguaniden | |
| CH380734A (de) | Verfahren zur Herstellung von neuen s-Triazinderivaten | |
| DE2345801A1 (de) | Pyridiniumsalze | |
| CH640220A5 (de) | Guanidiniumsalze, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende mikrobicide zubereitungen. | |
| DE2608135A1 (de) | Pesticide und ihre verwendung | |
| DE1493210C3 (enrdf_load_stackoverflow) | ||
| DE1493210C (de) | Bis-Guanidine und Bis-Biguanide und Verfahren zu deren Herstellung | |
| DE1923939A1 (de) | Fungicide | |
| DE2524578B2 (de) | 5-hydroxylaminomethylen-barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbicide | |
| DE1795021C3 (de) | Kupfer-II-Salze der L- und DL-2-Guanidino-13-thiazolincarbonsäure-4 oder ihrer Tautomeren, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2313020A1 (de) | Antibakteriell wirksame hexamethylenbis-biguanide | |
| DE1470421A1 (de) | Mehrbasische Verbindungen | |
| DE1668736A1 (de) | Verfahren zum Herstellen von substituierten Bisamidino-Verbindungen | |
| DE2536951B2 (de) | Triazapentadiene, Verfahren zu ihrer Herstellung und diese enthaltende insektizide Mittel | |
| DE1668616B2 (de) | Bisdithiocarbamte, verfahren zu deren herstellung und diese enthaltendes fungizides mittel | |
| DE1235287B (de) | Verfahren zur Herstellung von fungizid wirksamen Dodecylamin-Metallsalz-Komplexverbindungen der mono- und bis-Dithiocarbamidsaeuren | |
| DE1042569B (de) | Verfahren zur Herstellung von Amin-Zink-Komplexverbindungen der AEthylenbisdithiocarbaminsaeure | |
| AT234707B (de) | Verfahren zur Herstellung von neuen 2-Sulfa-4, 6-dialkyl-s-triazinen | |
| DE4142128C2 (de) | Verfahren zur Herstellung von Verbindungen mit einer oder mehreren Thiocyanatomethylthio-Gruppierungen | |
| CH437649A (de) | Desinfektions- und Hygienemittel |