DE2344010A1 - Neue 5-nitrochinolin-derivate, verfahren zur herstellung und diese enthaltende zusammensetzungen - Google Patents
Neue 5-nitrochinolin-derivate, verfahren zur herstellung und diese enthaltende zusammensetzungenInfo
- Publication number
- DE2344010A1 DE2344010A1 DE19732344010 DE2344010A DE2344010A1 DE 2344010 A1 DE2344010 A1 DE 2344010A1 DE 19732344010 DE19732344010 DE 19732344010 DE 2344010 A DE2344010 A DE 2344010A DE 2344010 A1 DE2344010 A1 DE 2344010A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- quinoline
- nitro
- formula
- carbon atoms
- 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
- 239000000203 mixture Substances 0.000 title claims description 23
- NDDZXHOCOKCNBM-UHFFFAOYSA-N 5-nitroquinoline Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=N1 NDDZXHOCOKCNBM-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 41
- 239000011149 active material Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- VQDUORNVUFSTEQ-UHFFFAOYSA-N [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(N(C)C)=O Chemical compound [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(N(C)C)=O VQDUORNVUFSTEQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229960003540 oxyquinoline Drugs 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003139 biocide Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 12
- 229920000940 maneb Polymers 0.000 description 12
- 238000011835 investigation Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 235000015097 nutrients Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000155 melt Substances 0.000 description 7
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000213004 Alternaria solani Species 0.000 description 5
- 230000003385 bacteriostatic effect Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 241001465180 Botrytis Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 241000588915 Klebsiella aerogenes Species 0.000 description 4
- 241000233622 Phytophthora infestans Species 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241001157812 Alternaria brassicicola Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000008223 sterile water Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WOSOHFBLZPFTTC-UHFFFAOYSA-N (5-nitroquinolin-8-yl) N,N-dibutylcarbamate Chemical compound [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(N(CCCC)CCCC)=O WOSOHFBLZPFTTC-UHFFFAOYSA-N 0.000 description 2
- GKPRSAKLBYSVKI-UHFFFAOYSA-N (5-nitroquinolin-8-yl) N-methylcarbamate Chemical compound [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(NC)=O GKPRSAKLBYSVKI-UHFFFAOYSA-N 0.000 description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical group CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- PCPJIDFJVZWDOX-UHFFFAOYSA-N 2-(isocyanatomethyl)oxolane Chemical compound O=C=NCC1CCCO1 PCPJIDFJVZWDOX-UHFFFAOYSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 241000221779 Fusarium sambucinum 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
- 239000005909 Kieselgur Substances 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
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241001441284 Zeidae Species 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 235000015190 carrot juice Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 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 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- OSWBZCCZJXCOGL-UHFFFAOYSA-N n,n-dibutylcarbamoyl chloride Chemical compound CCCCN(C(Cl)=O)CCCC OSWBZCCZJXCOGL-UHFFFAOYSA-N 0.000 description 1
- XHLLMVSEBKZODD-UHFFFAOYSA-N n-acetyl-n-methylcarbamoyl chloride Chemical compound CC(=O)N(C)C(Cl)=O XHLLMVSEBKZODD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
- C07D215/34—Carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7230894A FR2197512B1 (OSRAM) | 1972-08-31 | 1972-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2344010A1 true DE2344010A1 (de) | 1974-03-07 |
Family
ID=9103729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732344010 Pending DE2344010A1 (de) | 1972-08-31 | 1973-08-31 | Neue 5-nitrochinolin-derivate, verfahren zur herstellung und diese enthaltende zusammensetzungen |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4966683A (OSRAM) |
| BE (1) | BE804218A (OSRAM) |
| CA (1) | CA1010871A (OSRAM) |
| CH (1) | CH585718A5 (OSRAM) |
| DD (1) | DD107573A5 (OSRAM) |
| DE (1) | DE2344010A1 (OSRAM) |
| ES (1) | ES418331A1 (OSRAM) |
| FR (1) | FR2197512B1 (OSRAM) |
| GB (1) | GB1382571A (OSRAM) |
| HU (1) | HU167953B (OSRAM) |
| IL (1) | IL42969A (OSRAM) |
| IT (1) | IT990427B (OSRAM) |
| NL (1) | NL7311921A (OSRAM) |
| SU (2) | SU500756A3 (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0387510A1 (de) * | 1989-02-10 | 1990-09-19 | Bayer Ag | Substituierte 8-Carbamoyloxychinolin-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung zur Bekämpfung von Schädlingen |
| KR20210070320A (ko) * | 2018-09-29 | 2021-06-14 | 장슈 야홍 메디텍 코퍼레이션 리미티드 | 니트록솔린 전구약물 및 이의 용도 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2154636C1 (ru) * | 1999-07-30 | 2000-08-20 | Субоч Георгий Анатольевич | Способ получения 5-нитро-8-оксихинолина |
| TWI874355B (zh) * | 2020-02-14 | 2025-03-01 | 中國大陸商江蘇亞虹醫藥科技股份有限公司 | 硝羥喹啉前藥及其用途 |
| CN111514142B (zh) * | 2020-05-29 | 2021-04-06 | 江苏亚虹医药科技股份有限公司 | 含硝羟喹啉前药的药物组合物及其制备方法和应用 |
-
1972
- 1972-08-31 FR FR7230894A patent/FR2197512B1/fr not_active Expired
-
1973
- 1973-08-13 IL IL42969A patent/IL42969A/en unknown
- 1973-08-28 CA CA179,800A patent/CA1010871A/fr not_active Expired
- 1973-08-30 CH CH1245173A patent/CH585718A5/xx not_active IP Right Cessation
- 1973-08-30 IT IT52248/73A patent/IT990427B/it active
- 1973-08-30 ES ES418331A patent/ES418331A1/es not_active Expired
- 1973-08-30 SU SU1959055A patent/SU500756A3/ru active
- 1973-08-30 JP JP48096772A patent/JPS4966683A/ja active Pending
- 1973-08-30 BE BE135109A patent/BE804218A/xx unknown
- 1973-08-30 GB GB4081473A patent/GB1382571A/en not_active Expired
- 1973-08-30 NL NL7311921A patent/NL7311921A/xx not_active Application Discontinuation
- 1973-08-30 HU HURO744A patent/HU167953B/hu unknown
- 1973-08-31 DE DE19732344010 patent/DE2344010A1/de active Pending
- 1973-08-31 DD DD173206A patent/DD107573A5/xx unknown
-
1974
- 1974-10-14 SU SU2066959A patent/SU503519A3/ru active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0387510A1 (de) * | 1989-02-10 | 1990-09-19 | Bayer Ag | Substituierte 8-Carbamoyloxychinolin-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung zur Bekämpfung von Schädlingen |
| KR20210070320A (ko) * | 2018-09-29 | 2021-06-14 | 장슈 야홍 메디텍 코퍼레이션 리미티드 | 니트록솔린 전구약물 및 이의 용도 |
| KR102762016B1 (ko) | 2018-09-29 | 2025-02-05 | 장슈 야홍 메디텍 코퍼레이션 리미티드 | 니트록솔린 전구약물 및 이의 용도 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU167953B (OSRAM) | 1976-01-28 |
| JPS4966683A (OSRAM) | 1974-06-27 |
| IL42969A0 (en) | 1973-11-28 |
| IL42969A (en) | 1977-01-31 |
| BE804218A (fr) | 1974-02-28 |
| CH585718A5 (OSRAM) | 1977-03-15 |
| GB1382571A (en) | 1975-02-05 |
| FR2197512A1 (OSRAM) | 1974-03-29 |
| CA1010871A (fr) | 1977-05-24 |
| IT990427B (it) | 1975-06-20 |
| DD107573A5 (OSRAM) | 1974-08-12 |
| FR2197512B1 (OSRAM) | 1977-01-14 |
| SU500756A3 (ru) | 1976-01-25 |
| SU503519A3 (ru) | 1976-02-15 |
| ES418331A1 (es) | 1976-03-16 |
| NL7311921A (OSRAM) | 1974-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2164723C3 (de) | Antimikrobielles Mittel und seine Verwendung zur Bekämpfung von Bakterien, Pilzen und Algen | |
| DE2609280A1 (de) | Schaedlingsbekaempfungsmittel | |
| DE1568744A1 (de) | Verfahren zur Herstellung von Propinylaethern | |
| CH498814A (de) | Verfahren zur Herstellung von Methylen-bis-thiolsulfon-säureestern | |
| DE2344010A1 (de) | Neue 5-nitrochinolin-derivate, verfahren zur herstellung und diese enthaltende zusammensetzungen | |
| EP0094552B1 (de) | Jodpropargylammoniumsalze, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| DE2801868C2 (de) | Benzthiazolon- und Benzoxazolon-Derivate | |
| DE1542780A1 (de) | Fungitoxische Mittel | |
| DE2426653B2 (de) | Derivate des 2-Amino-1,3-thiazins | |
| DE2022370A1 (de) | N-Fluordichlormethylthio-sulfamidsaeure-Derivate,Verfahren zu ihrer Herstellung und ihre mikrobizide und fungizide Verwendung | |
| DE2419017A1 (de) | Isothiazolin-3-one | |
| DE2855695A1 (de) | 1-thiocyanato-8-substituierte naphthaline | |
| DE2736280C2 (de) | 2,5-dihalogenphenyl-β-substituierte Sulfone und diese enthaltende Mittel | |
| DE1670450C3 (de) | Tetrachloräthylthio-pyrazole mit fungiziden und bakteriziden Eigenschaften, Verfahren zu deren Herstellung und fungizide und bakterizide Mittel | |
| EP0081679A2 (de) | Substituierte Benzylimidazoliumsalze und diese enthaltende Mikrobizide | |
| DE1542974C (de) | Herbicides Mittel, enthaltend N-Halogenmethylcarbonyl^-azabicyclo- eckige Klammer auf 3,2,2 eckige Klammer zu -nonane | |
| DE69205155T2 (de) | Zusammensetzung und Verwendung von Dimucapto-substituierten Dinitrilen als antimikrobielle Mittel. | |
| DE2035145A1 (de) | Neue substituierte 2 Azabicycloalkane | |
| EP0001623A1 (de) | Aryl-thiocarbonsäure-thiocyanmethylester, ihre Herstellung und ihre Verwendung als Pestizide, sowie sie enthaltende Mittel | |
| DE2804271C2 (de) | Halogenierte Spirane und diese enthaltende Mittel | |
| DE1670455B2 (de) | l-(Polyhalogenalkylthio)-indazole, ein Verfahren zu deren Herstellung sowie fungizide und/oder bakterizide Mittel | |
| EP0159644B1 (de) | N-(Dichlorfluormethylthio)-3,4-dimethylmaleinimid, ein Verfahren zu seiner Herstellung und seine Verwendung | |
| DE3030192A1 (de) | Neue mikrobizide zum schutz technischer materialien | |
| DE2031236C3 (de) | Neue 10,11- Dihydrodibenzo (b,f) azepinderivate, ihre Herstellung und fungizide Zusammensetzungen | |
| AT331079B (de) | Mittel zur bekampfung von schadlichen mikroorganismen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |