CZ268198A3 - 2-hetaroylcyklohexan- 1,3-diony, způsob jejich výroby a jejich použití - Google Patents
2-hetaroylcyklohexan- 1,3-diony, způsob jejich výroby a jejich použití Download PDFInfo
- Publication number
- CZ268198A3 CZ268198A3 CZ982681A CZ268198A CZ268198A3 CZ 268198 A3 CZ268198 A3 CZ 268198A3 CZ 982681 A CZ982681 A CZ 982681A CZ 268198 A CZ268198 A CZ 268198A CZ 268198 A3 CZ268198 A3 CZ 268198A3
- Authority
- CZ
- Czechia
- Prior art keywords
- alkyl
- halogen
- alkoxy
- hydrogen
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 55
- 150000002367 halogens Chemical class 0.000 claims abstract description 55
- 239000001257 hydrogen Substances 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 38
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 1137
- 239000000460 chlorine Substances 0.000 claims description 639
- -1 C 1 -C 4 -nitro Chemical group 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 21
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 24
- 241000196324 Embryophyta Species 0.000 abstract description 21
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 150000003527 tetrahydropyrans Chemical class 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229940099990 ogen Drugs 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001559 benzoic acids Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000003003 phosphines Chemical group 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 240000007313 Tilia cordata Species 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 229910002666 PdCl2 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- 235000013311 vegetables Nutrition 0.000 description 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
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- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- GUGLPELUECBSDK-UHFFFAOYSA-N phenol;urea Chemical compound NC(N)=O.OC1=CC=CC=C1 GUGLPELUECBSDK-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 210000000614 rib Anatomy 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JFTZUZWJGUCSTE-UHFFFAOYSA-M sodium;methyl-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CS([O-])(=O)=S JFTZUZWJGUCSTE-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Předložený vynález se týká nových derivátů hetaroylu s herbicidním účinkem, způsobu výroby derivátů hetaroylu, prostředků, které tyto deriváty obsahují a použití těchto derivátů nebo prostředků, které je obsahují k hubení plevele.
Dosavadní......stav techn i ky
Herbicidně účinné 2-hetaroylcyk1ohexadiony jsou známé z literatury, například z WO 948988, WO 9404524 a EP 283261.
Herbicidní vlastnosti známých sloučenin a rovněž snášenlivost s kulturními rostlinami mohou však být uspokojivé pouze podmíněně.
Podstata vynálezu
Úkol předloženého vynálezu spočívá v nalezení nových 2-hetaroylcyk1ohexadionů se zlepšenými vlastnostmi.
Byly nalezeny deriváty hetaroylu vzorce I
kde mají substituenty následující význam:
·· · · » · · β » · · · • · · · <
• · 4
- 2 ···· ·· ♦ · « » · · ’ ·· ··
L, Μ vodík, Ci-Ce -alkyl, C2-Ce-a 1 keny 1 , C? -Ce -a 1 k i ny 1 ,
Ci -C4-a 1koxy, přičemž tyto skupiny mohou být případně substituovány jedním až pěti atomy halogenu nebo Ci -C4 -a 1 koxy, halogen, kyano, nitro,
X kyslík nebo síra, která může být substituována jedním nebo dvěma atomy kyblíku, n nula, jedna, dvě,
R1 vodík, Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-Ce-a 1 k i ny 1 ,
Ci-C4-a 1koxy, přičemž tyto skupiny mohou být případně substituovány jedním až pěti atomy halogenu nebo Ci -C4 -a 1 koxy, ha 1ogen, fenyl, který může být substituován jednoduše nebo několikanásobně následujícími skupinami: Ci-C4-alkyl, vodík, Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 ky 1 , C1-C4halogenalkoxy, halogen, nitro, kyano, Ci-C4-a 1 ky 1 oxykarbonyl,
R2 vodík, Ci-Ce-alkyl, C2-Ce-a 1 ke ny 1 , C2-Ce-a 1 k i ny 1 ,
Ci-C4-a 1koxy, přičemž tyto skupiny mohou být případně substituovány jedním až pěti atomy halogenu nebo Ci -C4 -a l koxy, halogen, fenyl, který může být substituován jednoduše nebo několikanásobně následujícími skupinami: Ci-C4-alkyl, vodík, Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 kyl , Ci-C4 halogenalkoxy, halogen, nitro, kyano, Ci -C4-a 1ky1 oxy·· ·· ·· · · « ·
- 3 ·· ·· «·· · · • · · »· ·· karbonyl, R2 a R3 mohou tvořit vazbu,
| vodík, | Ci -Ce | -alkyl, | C2 | - C6 -alkenyl , | C2 -Ce -alkinyl , |
| Ci -C4 -a 1 koxy, | přičemž | tyto | skupiny mohou být případně | ||
| subst i tuovány Ci -C4 -a 1 koxy, halogen, | jedním | až | pěti atomy | halogenu nebo | |
| fenyl, | který | může | být | subst i tuován | jednoduše nebo |
několikanásobně následujícími skupinami: Ci-C4-alkyl, vodík, Ci -C4 -a 1 koxy, Ci -C4 -ha 1 ogena 1 ky 1 , C1-C4ha1ogena1koxy, halogen, nitro, kyano, Ci-C4-a 1ky1oxykarbonyl , R2 a R3 mohou tvořit vazbu,
R4 vodík, Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-C6-a 1 k i ny 1 ,
Či-C4-a 1koxy, přičemž tyto skupiny mohou být případně substituovány jedním až pěti atomy halogenu nebo Ci -C4 -a 1 koxy, ha 1ogen, fenyl, který může být substituován jednoduše nebo několikanásobně následujícími skupinami: Ci-C4-alkyl, vodík, Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 kyl , C1-C4ha1ogena1koxy, halogen, nitro, kyano, Ci-C4-alkyloxykarbonyl , cyk1 o hexan-1,3-di on vázaný na dvou místech, vzorce II
II ve kterém mají substituenty následující význam:
•••Φ ·· • Φ φφ ) Φ · ·
I ΦΦΦ
ΦΦΦΦ
ΦΦ
| R5 , R^ a | R10 vodík, Ci-C4-alkyl, | ||
| v | R7 | vodík, Ci -C4 -a 1 ky 1 , C3 -C4 -cyk 1 oa 1 ky 1 , přičemž tyto skupiny mohou případně nést jeden až tři následující substituenty: halogen, Ci-C4-thioa1ky1 nebo Ci-C4-a 1 koxy, nebo | |
| * | Ci-C4-a 1 koxy, Ci-Ce-a 1 koxya 1 ky 1 , tetrahydro- pyranyl-3, tetrahydropyrony1-4, nebo | ||
| R7 a R9 | mohou tvořit společnou vazbu členný karbocyk1 ický prstenec, | nebo tří až šesti | |
| R8 | vodík, Ci-C4-alkyl, | ||
| R9 | vodík, Ci-C4-alkyl nebo skupina | COOR11 , | |
| R11 | Ci -C4-alkyl, | ||
| a rovněž | hospodářsky použitelné soli. | ||
| Sloučeniny vzroce I se obdrží tí | m, že se zreagují |
sloučeniny vzorce II s derivátem kyseliny benzoové vzorce III a převedou se na deriváty heteroylu vzorce I.
Rovnice 1
II
ΙΠ
Ve shora uvedené rovnici 1 má význam halogenu nebo OH a L, Μ, X, R1 uvedený význam.
T v uvedených vzorcích R2 , R3 , R4 a n dři ve akt i vováné 1 i teratury
První krok průběhu reakce, acylace, nastává obecně známým postupem, například přídavkem acylchloridu vzorce III (T=C1) nebo kyseliny karboxylové vzorce III, například dicyk1okarbod i i midy DCC nebo podobnými z známými prostředky (například diethylenazodikarboxylatem DEAD, 2-pyridinsu1fidem) trifeny1fosfinem, do roztoku nebo suspenze cyk1ohexadi onu vzorce II, případně za přítomnosti pomocné zásady. Reaktandy a pomocné látky se přitom přednostně používají v ekvimo1árních množstvích. Přitom může být výhodný malý přebytek pomocné zásady, vztaženo na látky vzorce II, například 1,2 až 1,5 molové ekvivalenty.
pyr idin mohou t o 1uo 1 ,
Jako pomocné zásady jsou vhodné nebo uhličitany alkalického kovu.
použít například methylenchlorid, acetonitril nebo ethylester kysel terciární alkylaminy, Jako rouzpouštěd1 a se dioxan, diethylether, i ny octové.
Během přídavku acylchloridu se reakční směs ochladí přednostně na 0 až 10 °C, potom se reakční směs při teplotě 20 až 100 °C, zejména 25 až 50 °C, míchá, až se ukončí reakce. Zpracování nastává obvyklým způsobem, například se reakční směs nasytí vodou a extrahuje se využitelný produkt, například • · · · • · • · · • · ··
- 6 methylenchloridem. Po usušení organické fáze a oddělení rozpouštědla se může surový enolester použít bez dalšího čištění k dalšímu přesmyku. Příklady výroby pro bezoylester cyklohexan-1,3-dionů se nalézají například v EP-A 186118 nebo
US 4 780 127.
Přesmyk enolesteru na sloučeniny vzorců Ia až Ie nastává v rozpouštědle přednostně při teplotách 20 až 40 °C a za přítomnosti pomocných zásad s pomocí kyanových sloučenin jako katalyzátoru.
Jako rozpouštědlo acetonitril, methylenchlorid, kyseliny octové nebo toluol. acetonitryl. Jako pomocná se může použít například
1,2-dichlorethan, ethylester Přednostním rozpouštědlem je látka jsou vhodné terciární alkylaminy, piridin nebo a 1kyluhliči taný, které se přednostně používají v ekvimolárním množství nebo i až ve čtyřnásobném přebytku, vztaženo na benzoylenoester. Přednostní pomocnou látkou je triethylamin ve dvojnásobném množství.
Jako katalyzátor jsou vhodné kyanid drasený, anhydrid acetokyanu, trimethysi 1ylkyanid, přednostně v množství 1 až 50 molových procent, vztaženo na enolester. Přednostně se přidává anhydrid acetokaynu, například v množství 5 až 15, přednostně 10 molových procent. Příklady přesmyčky enolesterů s kyanidem jako katalyzátorem jsou uvedeny například v EP-A 186118 nebo US 4 780 127.
Zpracování nastává známým způsobem, například se reakční směs okyselí zředěnými minerálními kyselinami jako 5 %ní kyselinou chlorovodíkovou nebo kyselinou sírovou a extrahuje se organickými rozpouštědly jako methylenchlorid nebo ethylester kyseliny octové. K čištění se extrakt extrahuje studeným 5 až 10 %ním roztokem uhličitanu alkalického kovu.
φφ φ φ φφφ φ
• φ • ΦΦΦ · φ • · · • φ φ • Φ φφ φ φ φφ přičemž konečný produkt přechází do vodnaté fáze. Okyselením vodnatého roztoku se vyloučí produkt vzorce Ia až le nebo se znovu extrahuje methylenchloridem nebo ethylesterem kyseliny octové, suší se a následně se uvolňuje rozpouštědlo.
Jako výchozí materiál používané 1,3-diketony vzorce II jsou známé a mohou se vyráhět známými postupy, které jsou popsány například v EP-A 71707, EP-A 142741, EP-A 243313, US 4,249,927 a WO 92/13821. Cyk1ohexadi on a dimedon jsou prodávané sloučeniny.
Deriváty kyseliny benzoové vzorce III lze vyrobit takto:
Benzoylha 1ogenidy, jako benzoylchloridy vzorce III (T=C1), se vyrobí známým způsobem reakcí benzoových kyselin vzorce III (T=OH) s thiony 1chloridem.
Benzoové kyseliny vzorce III (T=OH) se mohou vyrobit známým způsobem kyselou nebo zásaditou hydrolýzou z příslušných esterů vzorce III ( T= Ci-C4-a 1 koxy) .
Meziprodukty vzorce III lze popsat na základě částečně z literatury feno 1karboxylové známých kysel i ny sloučenin vzorce IV kyseliny vzorce V. Neznámé sloučeniny vytvořit použitím z Houben Weyl, Methoden a E 1 1 ) .
subst i tuováné thi o 1karboxylové jako nebo vzorce IV nebo V lze literatury známých reakcí (Literatura: der Organischen Chemie, svazek VI, IX
Další reakce na meziprodukty literatury známým způsobem (například J. Org. Chem. 1974, 39-1811, J. Am. Chem.
vzorce III probíhá z Synthesis 1975, 451,
Soc. 1954, 76, 1068,
Heterocyclic Compounds, svazek: Multi-Sulfur and Sulfur and • · * « «
I · ·· • · · · • · 1 • · ··
- 8 Oxygen Fi ve and Six-Membered Heterocyc1 es, J. Org. Chem. 1979, 44, 1977).
Rovnice 2
A)
VI (Z=Br, OH, OSO2CH3, OSO2P - CH3 - C6H4) vn
V
- 9 • Φφ · φφ • φ φ φφφ φ φ φ φ φ φ φ · φ φ φ φ φφ φ φ φ φ φ φ φ φ φφ « φ · φ · · φ φ φ φ φ φφ nebo
Ε)
Z=Br, ΟΗ, OSO2CH3,0SO2P - CH3 - C6H4
XIV
XV
(θ>η
XVI
Potom lze deriváty 2.3-dihydrobenz-1,4-oxathii nu, jaké jsou popsány například v rovnici 2A, vyrobit pomocí intramo1eku1ární nukleofi lni substituce na aromáty (X=O, S, T=OH, Ci-C4-a 1koxy), viz literaturu: J.Am. Chem. Soc. 76, 1068,
1954, J. Org. Chem. 44, 1977, 1979. Jak je znázorněno v rovnici pod písmeny D a E, lze fenoly nebo thioly alkylizovat alkylbromidy v alkalickém roztoku. Reaktandy přídavné látky se přitom přednostně používají v ekvimo1árních množstvích. Může být výhodný přebytek přídavné látky. Jako jsou uváděny alkoholy jako ethanol nebo alkoholáty, jako například alkoholát sodný může probíhat za normálního tlaku nebo při zvýšeném tlaku. Přednostní tlaková oblast je 1 až 10 bar. Reakční směs se míchá při 20 až 150 °C, zejména při 60 až 80 °C.
například tak, že se reakční směs lije na například hydroxid sodný a upotřebitelný produkt se může získat extrakcí například ethylesterem kyseliny octové, suší se a zbavuje se rozpouštědla.
rozpouštědla DMF a jako zásady nebo NaH. Reakce přednostně Zpracování nastává zředěný hydroxid,
Následně může například nastat záměna Z methanthiosu 1fonatem draselným v alkoholickém roztoku. Přednostními rozpouštědly jsou ethanol, methanol a isopropanol. Reakční směs se přitom míchá přednostně při 20 až 100 °C, zejména při 60 až 80 °C.
Zpracování nastává přednostně za přídavku vody, přičemž upotřebitelný produkt se odsává nebo se extrahuje • · • · ··· • · ··
-11extrakcí například methylenchloridem a suší se.
Cyklace nastává na kostru dihydrobenzoxathi i nu nebo dihydrobenzodithii nu za přídavku kyseliny lewisové rozpouštědle. Přitom jako kyselina lewisová je v inertním přednostní trichlorid hlinitý a jako inertní rozpouštědlo jsou přednostní nitromethan nebo methylenchlorid. Reakční směs se přitom udržuje při teplotě 20 až 50 °C., Zpracování nastává například přídavkem zředěné minerální kyseliny, jako například kyseliny chlorovodíkově a upotřebitelný produkt se odsává nebo se extrahuje extrakcí etherem, suší se a zbavuje se rozpouštědla.
Oxydací podle z dehydrogenací (Houben Weyl Band IV/1a a b) se mohou sl literatury známých postupů a/nebo Methoden der Organischen Synthese oučeniny dále upravovat.
Benzoové kyseliny vzorce III se mohou obdržet tím, že se zreagují vhodné sloučeniny substituované bromem nebo jodem vzorce XVIII za přítomnosti katalyzátoru tvořeného přechodovými kovy, paladiem, niklem, kobaltem nebo rhodiem a zásadou s oxidem uhelnatým a vodou za zvýšeného tlaku.
Rovnice 3 pricemz
XVIII
T je OH, Ci-C4-alkoxy a L, popsaný význam.
Μ, X, Rl až
III R2 a n mají shora
Katalyzátory nikl, kobalt rhodium a zejména paladium ·· ··
- 12 ··· · ·· • · · • · ·· • ··· · · ·· ·· mohou být kovové nebo v podobě obvyklých solí, jako například v podobě halogenových sloučenin, například PdCl2, RhCl3.H20, acetáty, například Pd(0Ac)2, kyanidy a podobně se známým mocenstvím. Rovněž se mohou použít kovové komplexy s terciárními fosfiny, a 1kylkarbony1y kovu, karbonyly kovu, například C02(C0)a, Ni(C0)4, komplexy karbonylu kovu s terciárními fosfiny, například (PPh3)2Ni(C0)2, nebo se solemi přechodových kovů komp1exováných terciárními fosfiny. Naposledy uvedené provedení je přednostní zejména v případě paladia jako katalyzátoru. Typ fosfinových ligand je přitom široce variabilní. Například mohou být popsány následujícími rovnicemi :
P
nebo
P-(CH2)k -
r!4
RlS přičemž k znamená čísla 1, 2, 3 nebo 4 a zbytky R1 2 až R15 značí nízkomolekulární alkyl, například Ci-Ce-alkyl, aryl, Ci-C4-a 1ky1aryl, například benzyl, fenethyl nebo aryloxy. Arylem je například naftyl, antryl a přednostně případně substituovaný fenyl, přičemž s ohledem na substituenty se dbá na inertnost vzhledem ke karboxylaci, mimo to mohou být široce variabilní a mohou zahrnovat všechny inertní uhlíkové organické zbytky, jako Ci-Ce-a 1 kyl o vé zbytky, například methyl , karboxylové zbytky jako COOH, COOM, M je například alkalický kov, kov alkalických zemin nebo amonná sůl, nebo uhlíkové organické zbytky spojené kyslíkem, jako Ci-C6-a 1koxy.
Výroba fosfinových komplexů se může provádět známým postupem, například jak je popsáno ve vpředu uvedených materiálech. Například se může vycházet z obvyklých komerčně za j i st i te 1 ných kovových solí jako PdCl2 nebo Pd(0C0CH3)2 a ·· ·· * · · • · · ··· · · • · · ·· ··
- 13 přidává se fosfin, například P(CeH5)3, P(n-C4H9)3, PCH3(CeH5)2 a 1,2-bis ( difeny1fosfi no)ethan.
···· ·♦
Množství fosfinu, vztaženo na přechodový kov, činí obvykle 0 až 20, zejména 0,1 až 10 molových ekvivalentů, zvláště přednostně 1 až 5 molových ekvivalentů.
Množství přechodového kovu není kritické. Samozřejmě se může z cenových důvodů použít spíše malé množství, například 0, 1 až 1 mol. %, zejména 1 až 5 mol. %, vztaženo na výchozí látku vzorce II, případně III.
K výrobě provádí reakce s množstvími vody.
benzoových kyselin oxidem uhelnatým a na výchozí vztaženo současně také sloužit jako rozpouštědlo množství není kritické.
vzorce III (T=OH) se alespoň ekvimolárními látku VI. Voda může to znamená maximální
Může být ale také výhodné podle a použitých katalyzátorů použít místo typu výchozích látek vody jiné inertní rozpouštědlo nebo použít jako rozpouštědlo látky používané pro karboxy1ac i.
Jako inertní rozpouštědla přichází pro karboxylaci do úvahy obvyklá rozpouštědla, jako uhlovodíky, například toluol, xylol, hexan, pentan, cyklohexan, ether, například methyl-terc. butylether, tetrahydrofuran, dioxan, dimethoxyethan, substituované amidy jako dimethylformamid, persubstituováné močoviny jako tetra-Ci -C4-a 1ky1močoviny nebo nitrily jako benzonitril nebo acetonitril.
V přednostním provedení způsobu se používají reakční složky, zejména zásady, v přebytku, takže není potřebné žádné přídavné rozpouštědlo.
·· ·· • · · • · ·· • · · · • · • · ··
- 14 Pro způsob vhodné zásady jsou všechny inertní zásady, které umožňují vázat při reakci uvolněný jodovodík, případně se uvádí terciární aminy, jako například aminy jako ···· ·· bromovodík. Jako příklad terciární alkylaminy, triethylamin, cyklické Ν,N'-d i me t hy1p i peraz i η, hydrouhliči taný alkalického substituované tetraaikylem, například tetramethylmočoví na jako nebo tr i a 1kylami ny,
N-methy1piperidin pyridin, uhličitany alkalického kovu, kovu, nebo močovinové deriváty jako tetra-Ci-C4-a 1ky1 močoví na,
Množství zásady není kritické, obvykle se používá 1 až 10, zejména 1 až 1 mol. Při současném použití zásady jako rozpouštědla se zpravidla používá takové množství, že se rozpustí reakční složky, přičemž se z praktických důvodů, k úspoře nákladů, k umožnění použití malých reakčních nádob a k zajištění maximálního kontaktu reakčních složek, zabraňuje nepotřebně vysokým přebytkům.
Během reakce se tlak oxidu uhelnatého nastaví tak, že je vždy přebytek oxidu uhelnatého, vztaženo na látku vzorce VI. Přednostně činí tlak oxidu uhelnatého při teplotě místnosti 1 až 250 barů, zejména 5 až 150 barů.
Karbony1 izace se provádí zpravidla při teplotách 20 až 250 °C, zejména při 30 až 150 °C kontinuálně nebo di skont inuá1 ně. Při di skont inuá1 ním provozu se výhodně k udržování konstantního tlaku kontinuálně na reakční směs působí tlakem oxidu uhelnatého.
výchoz í vhodnou reakcí.
Arylha 1ogenové sloučeniny vzorce sloučeniny jsou známé nebo se kombinací známých syntéz a shora
XVIII používané jako snadno mohou vyrobit popsanou posloupností • · · · 4 • · 4 ·· ·· ···· ·· • · 4 » · · 4 ·· ··
S ohledem na stanovené použití benzoylových derivátů obecného vzorce I přichází jako substituenty do úvahy následující zbytky:
L, vodík,
Ci-Ce-alkyl jako methyl, ethyl, propyi, 1-methy 1 ethy 1 , butyl,
1-methylpropy1, 2-methy1propy1, . 1,1-dimethy1ethy1, pentyl.
1-methy1butyl, 2-methy1buty1, propyi, 2,2-di methy1propy1,
1-methy1pentyl, 2-methylpentyl,
4-methy1pentyl, 1,1-dimethylbutyl,
1.3- d i methylbuty1,
3.3- d i methy1buty1,
1,2,2-trimethylpropyl,
1-ethyl-2-methyl-propyi,
3-methy1buty1, 1,1-dimethyl1-ethylpropy1, hexyl,
3-methy1pentyl,
1,2-d i methy1buty1,
2,2-dimethylbutyl, 2,3-dimethylbutyl,
1-ethylbutyl, 1,1,2-trimethylpropyl,
1-ethy1-1-methy1propy1 nebo zejména methyl, ethyl, 1-methyl ethyl, 1-methy1propyi,
2-methyl- propyi, 1,1-dimethy1ethy1 a 1,1-dimethy1propy1,
C2-Ce-a 1 keny1 jako 2-propenyl, 2-butenyl,
2- propenyl, 2-methy1-2-propenyl, 2-pentyl
3- methyl-2-propenyl, 2-pentyl, 3.pentyl, butenyl, 1-methyl-2-butenyl,
1-methyl-3-butenyl, 2-methyl-4-butenyl.
1, 1-dimethyl-2-própenyl, 1,2-d i methyl -2propenyl, 2-hexenyl, 3-hexenyl, 41-methyl-2-pentenyl,
4-methyl-2-pentenyl
1-methyl-3-pentenyl 4-methyl-3-pentenyl
3-methy1-4-pentenyl butenyl,
2-methyl-2-pentyl ,
3-methy1-2-pentenyl,
2-methyl-3-pentenyl , 1-methyl-4-pentenyl ,
4-methyl-4-pentenyl
3- butenyl, 1-methyl, 3-pentyl, 4-pentyl,
4-pentyl, 3-methyl-22- methyl-2-butenyl,
3- methyl-3-butenyl, própenyl, 1-ethyl-2hexenyl, 5-hexenyl,
3-methyl-2-pentyl,
4- methy1-2-pentenyl, 3-methy1-3-pentenyl,
2-methyl-4-pentenyl,
1, 1-d i methy1-2 - 16 • Φ · · • · · • · · • · · · · • · · ·· «φ
1,1-di methyl-3-butenyl , 1,2-dimethyl-2-butenyl, 1,3-dimethyl-3butenyl, 2,2-dimethy1-3-buteny1, 2,3-dimethy1-2-buteny1,
2,3-di methyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl ,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-tri methyl-2propylen, 1-ethyl-1-methyl-2-propenyl a ethyl-2-methy1-2propeny 1, zejména 1-methy 1-2-propenyl , 1 -me.t hyl -2-but eny 1 , 1,1-dimethy1 2-propenyl a 1, 1-dimethy1-2-butenyl,
C2-Ce-a 1kiny1 jako propargyl, ě-butinyl, 3-butenyl, 2-pentinyl,
3- pentlnyl, 4-pentinyl, 1-methyl-3-butinyl, 2-methyl-3-butinyl, 1-methyl-2-butinyl, 1,1-dimethy1-2-prop iny1, 1-ethyl-2propinyl, 1-ethyl-2-propinyl, 2-hexinyl, 3-hexínyi, 4-hexinyl,
5-hexinyl, 1-methy1-2~pentiny1, 1-methyl-3-pentinyl, 1-methyl4- pentinyl, 3-methyl-4-pentinyl, 4-methyl-2-pentinyl,
1,1-dimethyl-2-butinyl, 1,1-dimethyl-3-butinyl, 1,2-dimethy13-butinyl, 2,2-dimethy1-3-butiny1, 1-ethyl-2-butinyl, 1-ethyl3-butinyl, 2-ethyl-3-butinyl a 1-ethy1 -1-methy1-2-prop iny1,
Ci-C4-alkoxy jako methoxy, ethoxy, n-propoxy, 1-methylenethoxy, n-butoxy, 1-methy1propopxy, 2-methy1propoxy a 1,1-dimethylethoxy, zejména Ci-Cj-alkoxy jako methoxy, ethoxy, 1-propoxy, přičemž tyto skupiny mohou být rovněž substituovány, jako bylo uvedeno vpředu, jedním až pěti halogenovými atomy, jako je fluor, chlor, brom, jod, přednostně fluorem a chlorem nebo Ci -C4 -a 1 koxy.
Přednostní jsou deriváty hetaroylu vzorce Ia
ve kterém značí L vodík, Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-Ce ~a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 kyl , Ci-C4-ha 1ogen alkoxy, halogen, kyano nebo nitro a M vodík, Ci-Ce-alkyl, C2 -Ce -a 1 keny 1 , C2 -C6 -a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci-C4-ha 1 oge na 1 ky 1 , Ci —C4 -ha 1 ogena 1 koxy, halogen, kyano nebo nitro a Q, X, Ri až R4 a n mají shora uvedený význam.
Dále jsou přednostní deriváty hetaroylu vzorce Ib
ve kterém značí L Ci-Ce -alkyl, C2-Ce-a 1 kenyl , C2-C6-a 1 k i ny 1 , Ci —C4 -a 1 koxy, Ci -C4 -ha 1 ogena 1 kyl , Ci -C4 -ha 1 ogena 1 koxy, halogen, kyano nebo nitro a M vodík, Ci-C6-alkyl, C2 -Ce -a 1 keny 1 , C2-C6-alkinyl , Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 kyl ,
Ci-C4-ha 1 ogena 1 koxy, halogen, kyano nebo nitro a Q, X, Ri až R4 a n mají shora uvedený význam.
Přednostní jsou také deriváty hetaroylu vzorce I, ve které značí zbytky L a M vodík, methyl, methoxy, chlor, kyano, nitro a trif1uormethyl.
»· «« 0 ··
0 « » · · « ·♦ ··
C2 -Ce -alkenyl , Ci -C4 -ha 1 ogenve kterém C2 -Ce -alkinyl značí L vodík, . Ci-Ce -alkyl,
Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 ky 1 alkoxy, halogen, kyano nebo nitro a M vodík, Ci-Ce—alkyl, C2-Ce-a 1 kenyl , C2-Ce-a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 ky i , Ci-C4-ha 1 ogena 1 koxy, halogen, kyano nebo nitro a Q, Ri až R4 a n mají shora uvedený význam.
Přednostní jsou také deriváty hetaroylu vzorce Id
Id ve kterém značí L vodík, Ci-Ce-alkyi, C2 -Ce -a 1 ke ny 1 , C2 -Ce -alki nyl , Ci -C4 -a 1 koxy, Ci-C4-ha 1 ogena 1 kyl , Ci -C4 -ha 1 ogenalkoxy, halogen, kyano nebo nitro a M vodík, Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-Ce-a 1 k i ny 1 , Ci -C4 -a 1 koxy, Ci-C4-ha 1 ogena 1 ky 1 , Ci-C4-ha 1 ogena 1 koxy, halogen, kyano nebo nitro a O, Ri , R4 a n mají shora uvedený význam.
Přednostní jsou dále deriváty hetaroylu vzorce Id
R1
R4
L
Id ···· ··
9 9 99
- 19 ve které® značí L vodík, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkinyl, C1-C4-alkoxy, C1-C<-halogenalky1, C1-C<-halogenalkoxy, halogen, kyano nebo nitro a M vodík, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkinyl, C1-C<-alkoxy, C1-C4-halogenalkyl, Ci-C4-halogenalkoxy, halogen, kyano nebo nitro, m značí 0, 1 nebo 2 a Q, R1, R4 a n nají shora uvedený význam.
| Přednostní | jsou také deriváty hetaroylu | vzorce Ie | ||
| 0 M (í?>» 11 1 1' | R1 | |||
| -R2 | ||||
| LzJk JC | — R3 Ie | |||
| L II | R4 | |||
| (°)n | ||||
| ve kterém | znač i | L vodík, | C1-Ce-alkyl, | C2-Ce-alkenyl, |
| C2-Ce-alkinyl, | Cl -C4 | -alkoxy, Ci-C4 | -halogenalkyl, | C1-C4-halogen- |
alkoxy, halogen, kyano nebo nitro a M vodík, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkinyl, C1-C4-alkoxy, Ci-C4-halogenalkyl, C1-C4-halogenalkoxy, halogen, kyano nebo nitro, m značí 0, 1 nebo 2 a Q, R1 až R4 a n mají shora uvedený význam.
Zvláště výhodné jsou také deriváty hetaroylu vzorce I až Id, jejichž substituenty sestávají z kombinací přednostních substituentů.
Příklady provedeni vynálezu
Zvláště přednostní sloučeniny vzorce I jsou uvedeny v následujících tabulkách 1 až 6.
Tabulka 1 « «Ζ ·· · · Φ ···· 9
ΦΦΦΦ Φ · ΦΦΦ φφ ΦΦ ΦΦΦ ΦΦΦ 99 ··
| Poř.č. | RS | RS | R7 | RS | Μ | L | X | η |
| 1.261 | Η | Η | Η | Η | Η | Η | 0 | 0 |
| 1 . 262 | Η | Η | Η | Η | Η | Η | 0 | 2 |
| 1 . 263 | CH3 | CH3 | Η | Η | Η | Η | 0 | 0 |
| 1.264 | CH3 | CH3 | Η | Η | Η | Η | 0 | 2 |
| 1.265 | Η | Η | Η | CH3 | Η | Η | 0 | 0 |
| 1.266 | Η | Η | Η | CH3 | Η | Η | 0 | 2 |
| 1 .267 | Η | Η | CH3 | CH3 | Η | Η | 0 | 0 |
| 1 . 268 | Η | Η | CH3 | CH3 | Η | Η | 0 | 2 |
| 1 .269 | Η | Η | Η | Η | CH3 | Η | 0 | 0 |
| 1.270 | Η | Η | Η | Η | CH3 | Η | 0 | 2 |
| 1.271 | CH3 | CH3 | Η | Η | CH3 | Η | 0 | 0 |
| 1.272 | CH3 | CH3 | Η | Η | CH3 | Η | 0 | 2 |
| 1 . 273 | Η | Η | Η | CH3 | CH3 | Η | 0 | 0 |
| 1 .274 | Η | Η | Η | CH3 | CH3 | Η | 0 | 2 |
| 1 .275 | Η | Η | CH3 | CH3 | CH3 | Η | 0 | 0 |
| 1.276 | Η | Η | CH3 | CH3 | CH3 | Η | 0 | 2 |
| 1.277 | Η | Η | Η | Η | C1 | Η | 0 | 0 |
| 1 .278 | Η | Η | Η | Η | C1 | Η | 0 | 2 |
···· ·· ··» ·» • · · · 1 • · ι ·· ··
| 1 . 279 | ch3 | Cfc | H | H | Cl | H | 0 | 0 |
| 1.280 | Cfc | Cfc | H | H | Cl | H | 0 | 2 |
| 1.281 | H | H | H | Cfc | Cl | H | 0 | 0 |
| 1 . 282 | H | H | H | Cfc | Cl | H | 0 | 2 |
| 1.283 | H | H | Cfc | Cfc | Cl | H | 0 | 0 |
| 1 . 284 | H | H | Cfc | Cfc | Cl | H | 0 | 2 |
| 1.285 | H | H | H | H | Cl | Cl | 0 | 0 |
| 1.286 | H | H | H | H | Cl | Cl | 0 | 2 |
| 1 . 287 | CH3 | Cfc | H | H | Cl | Cl | 0 | 0 |
| 1.288 | ch3 | Cfc | H | H | Cl | Cl | 0 | 2 |
| 1.289 | H | H | H | Cfc | Cl | Cl | 0 | 0 |
| 1.290 | H | H | H | Cfc | Cl | Cl | 0 | 2 |
| 1.291 | H | H | Cfc | Cfc | Cl | Cl | 0 | 0 |
| 1.292 | H | H | Cfc | Cfc | Cl | Cl | 0 | 2 |
| 1 . 293 | H | H | H | H | Cfc | Cfc | 0 | 0 |
| 1 . 294 | H | H | H | H | Cfc | Cfc | 0 | 2 |
| 1 . 295 | Cfc | Cfc | H | H | Cfc | Cfc | 0 | 0 |
| 1 . 296 | Cfc | Cfc | H | H | Cfc | Cfc | 0 | 2 |
| 1 . 297 | H | H | H | CH | Cfc | Cfc | 0 | 0 |
| 1 . 298 | H | H | H | CH | Cfc | Cfc | 0 | 2 |
| 1 . 299 | H | H | Cfc | CH | Cfc | Cfc | 0 | 0 |
| 1.300 | H | H | Cfc | CH | Cfc | Cfc | 0 | 2 |
| 1.301 | H | H | H | H | N02 | H | 0 | 0 |
| 1.302 | H | H | H | H | N02 | H | 0 | 2 |
| 1 . 303 | Cfc | Cfc | H | H | N02 | H | 0 | 0 |
| 1 . 304 | Cfc | Cfc | H | H | N02 | H | 0 | 2 |
φφφφ • · · φ φ φ φ φφφφ φ φφφφ φ φ φφφ φφ φφ φφφ φφφ φφ · *
| 1.305 | Η | Η | Η | CH3 | ΝΟζ | Η | 0 | 0 |
| 1.306 | Η | Η | Η | CHs | Ν02 | Η | 0 | 2 |
| 1.307 | Η | Η | CH3 | CH3 | Ν02 | Η | 0 | 0 |
| 1 . 308 | Η | Η | CH3 | CH3 | Ν02 | Η | 0 | 2 |
| 1.309 | Η | Η | Η | Η | 0CH3 | Η | 0 | 0 |
| 1.310 | Η | Η | Η | Η | 0CH3 | Η | 0 | 2 |
| 1.311 | CHz | CH3 | Η | Η | 0CH3 | Η | 0 | 0 |
| 1.312 | CH3 | CHs | Η | Η | 0CH3 | Η | 0 | 2 |
| 1.3 13 | Η | Η | Η | CH3 | 0CH3 | Η | 0 | 0 |
| 1.314 | Η | Η | Η | CHs | 0CH3 | Η | 0 | 2 |
| 1.315 | Η | Η | CH3 | CH3 | 0CH3 | Η | 0 | 0 |
| 1.316 | Η | Η | CH3 | CHs | OCHs | Η | 0 | 2 |
| 1.317 | Η | Η | Η | Η | Η | Η | S | 0 |
| 1.3 18 | Η | Η | Η | Η | Η | Η | S | 2 |
| 1.319 | CH3 | CH3 | Η | Η | Η | Η | S | 0 |
| 1.320 | CH3 | CH3 | Η | Η | Η | Η | S | 2 |
| 1.321 | Η | Η | Η | CH3 | Η | Η | S | 0 |
| 1.322 | Η | Η | Η | CH3 | Η | Η | S | 2 |
| 1.323 | Η | Η | CH3 | CHs | Η | Η | S | 0 |
| 1 . 324 | Η | Η | CH3 | CH3 | Η | Η | S | 2 |
| 1 .325 | Η | Η | Η | Η | CHs | Η | S | 0 |
| 1.326 | Η | Η | Η | Η | CHs | Η | S | 2 |
| 1.327 | CH3 | CHs | Η | Η | CH3 | Η | S | 0 |
| 1 . 328 | CH3 | CH3 | Η | Η | CHs | Η | S | 2 |
| 1 .329 | Η | Η | Η | CH3 | CH3 | Η | S | 0 |
| 1 .330 | Η | Η | Η | CH3 | CH3 | Η | S | 2 |
| 1.331 | Η | Η | CH3 | CH3 | CHs | Η | S | 0 |
• » · · · * · · · • · · · · · * fl··· · ··· · fl ··· •fl ·· ··· fl·· ·· ··
| 1 .332 | H | H | CH3 | CH3 | CH3 | H | s | 2 |
| 1 .333 | H | H | H | H | Cl | H | s | 0 |
| 1 .334 | H | H | H | H | Cl | H | s | 2 |
| 1.335 | CH3 | CH3 | CH3 | H | Cl | H | s | 0 |
| 1 . 336 | CH3 | CHs | H | H | Cl | H | s | 2 |
| 1 .337 | H | H | H | ch3 | Cl | H | s | 0 |
| 1.338 | H | H | H | CH3 | Cl | H | s | 2 |
| 1.339 | H | H | CH3 | CH3 | Cl | H | s | 0 |
| 1 .340 | H | H | ch3 | ch3 | Cl | H | s | 2 |
| 1.341 | H | H | H | H | Cl | Cl | s | 0 |
| 1 .342 | H | H | H | H | Cl | Cl | s | 2 |
| 1 , 343 | CH3 | CH3 | H | H | Cl | Cl | s | 0 |
| 1 .344 | CH3 | CH3 | H | H | Cl | Cl | s | 2 |
| 1.345 | H | H | H | CH3 | Cl | Cl | s | 0 |
| 1 .346 | H | H | H | CH3 | Cl | Cl | s | 2 |
| 1 .347 | H | H | CH3 | CH3 | Cl | Cl | s | 0 |
| 1.348 | H | H | CH3 | CH3 | Cl | Cl | s | 2 |
| 1.349 | H | H | H | H | CH3 | CH3 | s | 0 |
| 1 . 350 | H | H | H | H | CH3 | CH3 | s | 2 |
| 1.351 | CH3 | CH3 | H | H | CH3 | CH3 | s | 0 |
| 1.352 | CH3 | CH3 | H | H | CH3 | Cřfc | s | 2 |
| 1 .353 | H | H | H | CH3 | CH3 | CH3 | s | 0 |
| 1.354 | H | H | H | Cřfc | CH3 | ch3 | s | 2 |
| 1.355 | H | H | CH3 | CH3 | CH3 | CH3 | s | 0 |
| 1 . 356 | H | H | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 1 . 357 | H | H | H | H | N02 | H | s | 0 |
| 1 . 358 | H | H | H | H | NO? | H | s | 2 |
• · ·« · · · · · · · · • · · · · · ··· «· · · «·* ··· · ··
| 1 . 359 | Cfe | Cfe | H | H | NO? | H | S | 0 |
| 1 . 360 | Cfe | Cfe | H | H | NO? | H | S | 2 |
| 1.361 | H | H | H | Cfe | NO? | H | S | 0 |
| 1 . 362 | H | H | H | Cfe | NO? | H | s | 2 |
| 1.363 | H | H | Cfe | Cfe | NO? | H | s | 0 |
| 1.364 | H | H | Cfe | Cfe | NO? | H | s | 2 |
| 1.365 | H | H | H | H | OCfe | H | s | 0 |
| 1.366 | H | H | H | H | OCfe | H | s | 2 |
| 1.367 | Cfe | Cfe | H | H | OCfe | H | s | 0 |
| 1.368 | ch3 | Cfe | H | H | OCfe | H | s | 2 |
| 1 . 369 | H | H | H | Cfe | OCfe | H | s | 0 |
| 1 .370 | H | H | H | Cfe | OCfe | H | s | 2 |
| 1.371 | H | H | Cfe | Cfe | OCfe | H | s | 0 |
| 1.372 | H | H | Cfe | Cfe | OCfe | H | s | 2 |
| 1 . 373 | H | H | H | H | H | H | so? | 0 |
| 1 . 374 | H | H | H | H | H | H | so? | 2 |
| 1.375 | ch3 | Cfe | H | H | H | H | so? | 0 |
| 1 . 376 | Cfe | Cfe | H | H | H | H | SO2 | 2 |
| 1.377 | H | H | H | Cfe | H | H | so? | 0 |
| 1.378 | H | H | H | Cfe | H | H | so? | 2 |
| 1 . 379 | H | H | Cfe | Cfe | H | H | so? | 0 |
| 1 . 380 | H | H | Cfe | Cfe | H | H | so? | 2 |
| 1.381 | H | H | H | H | Cfe | H | so? | 0 |
| 1 . 382 | H | H | H | H | Cfe | H | so? | 2 |
| 1 . 383 | Cfe | Cfe | H | H | Cfe | H | so? | 0 |
| 1 . 384 | Cfe | Cfe | H | H | Cfe | H | so? | 2 |
| 1 . 385 | H | H | H | Cfe | Cfe | H | so? | 0 |
···· · · · · · «· ·· ··· ··· ·· ··
| 1 . 386 | Η | Η | Η | CH3 | CH3 | H | S02 | 2 |
| 1 . 387 | Η | Η | CH3 | CH3 | CH3 | H | S02 | 0 |
| 1 . 388 | Η | Η | CH3 | CH3 | CH3 | H | SO2 | 2 |
| 1 . 389 | Η | Η | Η | Η | C1 | H | S02 | 0 |
| 1.390 | Η | Η | Η | Η | C1 | H | S02 | 2 |
| 1.391 | CH3 | CH3 | Η | Η | C1 | H | S02 | 0 |
| 1 . 392 | ch3 | CH3 | Η | Η | C1 | H | SO2 | 2 |
| 1.393 | Η | Η | Η | CH3 | C1 | H | SO2 | 0 |
| 1.394 | Η | Η | Η | CH3 | C1 | H | SO2 | 2 |
| 1.395 | Η | Η | CH3 | CH3 | C1 | H | S02 | 0 |
| 1.396 | Η | Η | CH3 | CH3 | C1 | H | S02 | 2 |
| 1.397 | Η | Η | Η | Η | C1 | Cl | SO2 | 0 |
| 1.398 | Η | Η | Η | Η | C1 | Cl | SO2 | 2 |
| 1.399 | CH3 | CH3 | Η | Η | C1 | CI | SO2 | 0 |
| 1.400 | CH3 | CH3 | Η | Η | C1 | Cl | S02 | 2 |
| 1.401 | Η | Η | Η | CH3 | C1 | Cl | SO2 | 0 |
| 1.402 | Η | Η | Η | CH3 | C1 | Cl | S02 | 2 |
| 1 . 403 | Η | Η | CH3 | CH3 | C1 | Cl | S02 | 0 |
| 1.404 | Η | Η | CH3 | CH3 | C1 | Cl | S02 | 2 |
| 1 . 405 | Η | Η | Η | Η | CH3 | ch3 | S02 | 0 |
| 1.406 | Η | Η | Η | Η | CH3 | CH3 | S02 | 2 |
| 1 . 407 | CH3 | CH3 | Η | Η | ch3 | CH3 | S02 | 0 |
| 1 . 408 | CH3 | CH3 | Η | Η | CH3 | H | S02 | 2 |
| 1 . 409 | Η | Η | Η | CH3 | CH3 | CH3 | S02 | 0 |
| 1.410 | Η | Η | Η | CH3 | ch3 | CH3 | S02 | 2 |
| 1.411 | Η | Η | CH3 | CH3 | ch3 | CH3 | SO2 | 0 |
| 1.412 | Η | Η | CH3 | CH3 | ch3 | CH3 | SO2 | 2 |
• · · · • · · · · · ·· c ·· · · ···· • · · · · · · ·· · * · · · · · · · · « · · · · · ··· ·· ·· ··· ··· ·· 99
| 1.413 | Η | Η | Η | H | NOz | H | SOz | 0 |
| 1.414 | Η | Η | Η | H | NOz | H | SOz | 2 |
| 1.415 | CH3 | CH3 | Η | H | NOz | H | SO2 | 0 |
| 1.416 | CH3 | CH3 | Η | H | NOz | H | SOz | 2 |
| 1.417 | Η | Η | Η | CH3 | NOz | H | SO2 | 0 |
| 1.418 | Η | Η | Η | CH3 | N02 | H | SO2 | 2 |
| 1.419 | Η | Η | CH3 | CHs | NOz | H | SOz | 0 |
| 1 . 420 | Η | Η | CH3 | CH3 | NOz | H | SOz | 2 |
| 1.421 | Η | Η | Η | H | 0CH3 | H | SOz | 0 |
| 1 . 422 | Η | Η | Η | H | OCH3 | H | SOz | 2 |
| 1 . 423 | CH3 | CH3 | Η | H | OCH3 | H | SOz | 0 |
| 1 .424 | CH3 | CH3 | Η | H | OCH3 | H | SOz | 2 |
| 1 . 425 | Η | Η | Η | CH3 | OCH3 | H | SOz | 0 |
| 1 . 426 | Η | Η | Η | CH3 | OCH3 | H | SOz | 2 |
| 1 . 427 | Η | Η | CH3 | CH3 | OCH3 | H | SOz | 0 |
| 1 . 428 | Η | Η | CH3 | CH3 | OCH3 | H | SOz | 2 |
| 1.429 | Η | Η | 2-ethylthiopropyl | H | H | H | 0 | 0 |
| 1 . 430 | Η | Η | 2-ethy1thi οpropy 1 | H | H | H | 0 | 2 |
| 1.431 | Η | Η | 2-ethylthiopropyl | H | CH3 | H | 0 | 0 |
| 1 . 432 | Η | Η | 2-ethylthiopropyl | H | CH3 | H | 0 | 2 |
| 1 . 433 | Η | Η | 2-ethylthiopropyl | H | Cl | H | 0 | 0 |
| 1.434 | Η | Η | 2-ethylthiopropyi | H | Cl | H | 0 | 2 |
| 1 . 435 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | 0 | 0 |
| 1 . 436 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | 0 | 2 |
| 1 .437 | Η | Η | 2-ethylthi opropy 1 | H | CH3 | CH3 | 0 | 0 |
| 1 . 438 | Η | Η | 2-ethylthiopropyl | H | CH3 | CH3 | 0 | 2 |
| 1.439 | Η | Η | 2-ethylthiopropyl | H | NOz | H | 0 | 0 |
000000 · 0 0 0 • 0 · 0 » 0000
00 0 0 · 0000
000· 0 0 00
00 000 000 00 00
| 1.440 | Η | Η | 2-ethylthiopropyl | H | N02 | H | 0 | 2 |
| 1.441 | Η | Η | 2-ethylthiopropyl | H | och3 | H | 0 | 0 |
| 1 . 442 | Η | Η | 2-ethylthiopropyl | H | och3 | H | 0 | 2 |
| 1.443 | Η | Η | 2-ethylthiopropyl | H | H | H | S | 0 |
| 1.444 | Η | Η | 2-ethylthi opropyl | H | H | H | S | 2 |
| 1 . 445 | Η | Η | 2-ethylthiopropyl | H | CH3 | H | S | 0 |
| 1 . 446 | Η | Η | 2-ethylthiopropyl | H | ch3 | H | S | 2 |
| 1 . 447 | Η | Η | 2-ethylthiopropýl | H | Cl | H | S | 0 |
| 1 . 448 | Η | Η | 2-ethylthiopropyl | H | Cl | H | S | 2 |
| 1.449 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | S | 0 |
| 1 . 450 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | S | 2 |
| 1.451 | Η | Η | 2-ethylthiopropyl | H | Cřfe | CH3 | S | 0 |
| 1 . 452 | Η | Η | 2-ethylthiopropyl | H | CH3 | ch3 | S | 2 |
| 1 . 453 | Η | Η | 2-ethylthiopropyl | H | H | H | SO2 | 0 |
| 1 . 454 | Η | Η | 2-ethylthiopropyl | H | H | H | SO2 | 2 |
| 1 . 455 | Η | Η | 2-ethylthiopropyl | H | CH3 | H | SO2 | 0 |
| 1 . 456 | Η | Η | 2-ethylthiopropyl | H | ch3 | H | SO2 | 2 |
| 1 . 457 | Η | Η | 2-ethylthiopropyl | H | Cl | H | SO2 | 0 |
| 1 .458 | Η | Η | 2-ethylthiopropyl | H | Cl | H | SOz | 2 |
| 1 . 459 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | SO2 | 0 |
| 1.460 | Η | Η | 2-ethylthiopropyl | H | Cl | Cl | SO2 | 2 |
| 1.461 | Η | Η | 2-ethylthiopropyl | H | CH3 | ch3 | SOz | 0 |
| 1 . 462 | Η | Η | 2-ethylthi opropyl | H | ch3 | ch3 | SOz | 2 |
| 1 . 463 | Η | Η | tetrahydropyrany1-3 | H | H | H | 0 | 0 |
| 1 . 464 | Η | Η | tetrahydropyramy1-3 | H | H | H | 0 | 2 |
| 1 . 465 | Η | Η | tetrahydropyramy 1-3 | H | ch3 | H | 0 | 0 |
| 1 . 466 | Η | Η | tetrahydropyramyl-3 | H | ch3 | H | 0 | 0 |
··· · · v··· • · · · · · · · · · · 9
9 9 9 9 9 9 9 9 ·· ··· ··· 99 99
| 1.467 | Η | Η | tetrahydropyrany 1 -3 | H | Cl | H | 0 | 0 |
| 1.468 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | 0 | 2 |
| 1.469 | Η | Η | tetrahydropyranyl-3 | H | Cl | Cl | 0 | 0 |
| 1 . 470 | Η | Η | tetrahydropyrany 1 -3 | H | Cl | Cl | 0 | 2 |
| 1.471 | Η | Η | tetrahydropyranyl-3 | H | CH3 | CH3 | 0 | 0 |
| 1 . 472 | Η | Η | tetrahydropyrany 1 -3 | H | CH3 | CH3 | 0 | 2 |
| 1 . 473 | Η | Η | tetrahydropyranyl-3 | H | NO? | H | 0 | 0 |
| 1.474 | Η | Η | tetrahydropyranyl-3 | H | NO? | H | 0 | 2 |
| 1.475 | Η | Η | tetrahydropyranyl-3 | H | OCH3 | H | 0 | 0 |
| 1.476 | Η | Η | tetrahydropyrany 1 -3 | H | OCH3 | H | 0 | 2 |
| 1 . 477 | Η | Η | tetrahydropyrany1-3 | H | H | H | s | 0 |
| 1 . 478 | Η | Η | tetrahydropyranyl-3 | H | H | H | s | 2 |
| 1 . 479 | Η | Η | tetrahydropyranyl-3 | H | CH3 | H | s | 0 |
| 1 . 480 | Η | Η | tetrahydropyrany 1 -3 | H | CH3 | H | s | 2 |
| 1.481 | Η | Η | tetrahydropyrany 1 -3 | H | Cl | H | s | 0 |
| 1 . 482 | Η | Η | tetrahydropyrany1-3 | H | Cl | H | s | 2 |
| 1 . 483 | Η | Η | tetrahydropyranyl-3 | H | Cl | Cl | s | 0 |
| 1.484 | Η | Η | tetrahydropyranyl -3 | H | Cl | Cl | s | 2 |
| 1 .485 | Η | Η | tetrahydropyrany 1 -3 | H | CH3 | CH3 | s | 0 |
| 1 . 486 | Η | Η | tetrahydropyranyl-3 | H | CH3 | CH3 | s | 2 |
| 1.487 | Η | Η | tetrahydropyranyl-3 | H | H | H | so? | 0 |
| 1.488 | Η | Η | tetrahydropyranyl-3 | H | H | H | so? | 2 |
| 1 . 489 | Η | Η | tetrahydropyranyl-3 | H | CH3 | H | so? | 0 |
| 1 . 490 | Η | Η | tetrahydropyranyl-3 | H | CH3 | H | SO2 | 2 |
| 1.491 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | SO2 | 0 |
| 1 . 492 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | so? | 2 |
| 1.493 | Η | Η | tetrahydropyranyl-3 | H | Cl | Cl | so? | 0 |
·· · « ·
| 1.494 | Η | Η | tetrahydropyranyl -3 | H | Cl | Cl | SOz | 2 |
| 1 .495 | Η | Η | tetrahydropyranyl-3 | H | CH3 | ch3 | SO2 | 0 |
| 1 . 496 | Η | Η | tetrahydropyranyl-3 | H | ch3 | ch3 | SO2 | 2 |
| 1 .497 | Η | Η | tetrahydropyranyl-3 | H | ch3 | H | O | 2 |
| 1.498 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | 0 | 2 |
| 1.499 | Η | Η | t etrahydropyrany1-3 | H | Cl | Cl | 0 | 2 |
| 1.500 | Η | Η | tetrahydropyranyl -3 | H | ch3 | ch3 | O | 2 |
| 1.501 | Η | Η | tetrahydropyrany 1 -3 | H | ch3 | H | S | 2 |
| 1 . 502 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | S | 2 |
| 1.503 | Η | Η | tetrahydropyranyl-3 | H | ch3 | H | SO2 | 2 |
| 1.504 | Η | Η | tetrahydropyranyl-3 | H | Cl | H | SO2 | 2 |
| 1.505 | Η | Η | 1-methylthi ocyk1 o propyl | H | ch3 | H | 0 | 2 |
| 1.506 | Η | Η | 1-methylthi ocyk1 o propyl | H | Cl | H | 0 | 2 |
| 1.507 | Η | Η | 1-methylthi ocyk1 o propyl | H | Cl | H | 0 | 2 |
| 1.508 | Η | Η | 1-methylthi ocyk1 o propyl | H | ch3 | CH3 | O | 2 |
| 1 .509 | Η | Η | 1-methylthi ocyk1 o propyl | H | CH3 | H | s | 2 |
| 1.510 | Η | Η | 1-methylthi ocyk1 o propyl | H | Cl | H | s | 2 |
| 1.511 | Η | Η | 1-methylthi ocyk1 o propyl | H | CH3 | H | SO2 | 2 |
| 1.512 | Η | Η | 1-methylthi ocyk1 o propyl | H | Cl | H | SO2 | 2 |
| 1.513 | Η | Η | ( di methoxy) methyl | H | ch3 | H | O | 2 |
| 1.514 | Η | Η | (di methoxy)methyl | H | Cl | H | O | 2 |
| 1.515 | Η | Η | (d i methoxy)methyl | H | Cl | Cl | 0 | 2 |
| 1.516 | Η | Η | (di methoxy)methy 1 | H | CH3 | CHs | 0 | 2 |
···· ·· • · · · · ···· • · · · · · · ···· · • · · · · ··· «· ·· ··· ··· ·· ··
| 1.517 | Η | Η | ( d i methoxy) methy 1 | H | CH3 | H | S | 2 |
| 1.518 | Η | Η | (d i methoxy)methy1 | H | Cl | H | s | 2 |
| 1.519 | Η | Η | (d i methoxy)methy1 | H | CH3 | H | S02 | 2 |
| 1 .520 | Η | Η | (dimethoxy)methyl | H | Cl | H | SO2 | 2 |
Tabulka 2
| Poř.č. | RS | R6 | R7 | R8 | L | M | X | n |
| 2 . 1 | H | H | H | H | CH3 | H | 0 | 0 |
| 2.2 | H | H | H | H | CH3 | H | 0 | 2 |
| 2.3 | CH3 | CH3 | H | H | CH3 | H | 0 | 0 |
| 2.4 | CH3 | CH3 | H | H | ch3 | H | 0 | 2 |
| 2.5 | H | H | H | CH3 | CH3 | H | 0 | 0 |
| 2.6 | H | H | H | CH3 | CH3 | H | 0 | 2 |
| 2.7 | H | H | CH3 | CH3 | CH3 | H | 0 | 0 |
| 2.8 | H | H | CH3 | CH3 | ch3 | H | 0 | 2 |
| 2.9 | H | H | H | H | Cl | H | 0 | 0 |
| 2.10 | H | H | H | H | Cl | H | 0 | 2 |
| 2.11 | CH3 | CH3 | H | H | Cl | H | 0 | 0 |
| 2.12 | CH3 | CH3 | H | H | Cl | H | 0 | 2 |
| 2.13 | H | H | H | CH3 | Cl | H | 0 | 0 |
| 2.14 | H | H | H | CH3 | c 1 | H | 0 | 2 |
| 2.15 | H | H | CH3 | CH3 | Cl | H | 0 | 0 |
| 2.16 | H | H | CH3 | CH3 | Cl | H | 0 | 2 |
| 2.17 | H | H | H | H | Cl | Cl | 0 | 0 |
| 2.18 | H | H | H | H | Cl | Cl | 0 | 2 |
Β Β ΒΒ
Β Β Β Β Β Β Β β · • · 9 9 9 9 9 99 9 9 9
9 9 9 9 9 9 9
99 999 999 99 99
| Po ř.č. | R5 | R6 | R7 | R3 | L | Μ | X | η |
| 2.19 | CH3 | Cfo | Η | Η | C1 | C1 | 0 | 0 |
| 2.20 | CH3 | Cfo | Η | Η | C1 | C1 | 0 | 2 |
| 2.21 | Η | Η | Η | Cfo | C1 | C1 | 0 | 0 |
| 2.22 | Η | Η | Η | Cfo | C1 | C1 | 0 | 2 |
| 2.23 | Η | Η | Cfo | Cfo | C1 | C1 | 0 | 0 |
| 2.24 | Η | Η | Cfo | Cfo | C1 | C1 | 0 | 2 |
| 2.25 | Η | Η | Η | Η | Cfo | Cfo | 0 | 0 |
| 2.26 | Η | Η | Η | Η | Cfo | Cfo | 0 | 2 |
| 2.27 | CH3 | Cfo | Η | Η | Cfo | Cfo | 0 | 0 |
| 2.28 | CH3 | Cfo | Η | Η | Cfo | Cfo | 0 | 2 |
| 2.29 | Η | Η | Η | Cfo | Cfo | Cfo | 0 | 0 |
| 2.30 | Η | Η | Η | Cfo | Cfo | Cfo | 0 | 2 |
| 2.31 | Η | Η | Cfo | Cfo | Cfo | Cfo | 0 | 0 |
| 2.32 | Η | Η | Cfo | Cfo | Cfo | Cfo | 0 | 2 |
| 2.33 | Η | Η | Η | Η | Cfo | Η | S | 0 |
| 2.34 | Η | Η | Η | Η | Cfo | Η | S | 2 |
| 2.35 | Cfo | Cfo | Η | Η | Cfo | Η | S | 0 |
| 2.36 | Cfo | Cfo | Η | Η | Cfo | Η | S | 2 |
| 2.37 | Η | Η | Η | Cfo | Cfo | Η | S | 0 |
| 2.38 | Η | Η | Η | Cfo | Cfo | Η | S | 2 |
| 2.39 | Η | Η | Cfo | Cfo | Cfo | Η | S | 0 |
| 2.40 | Η | Η | Cfo | Cfo | Cfo | Η | S | 2 |
| 2.41 | Η | Η | Η | Η | C1 | Η | S | 0 |
| 2 . 42 | Η | Η | Η | Η | C1 | Η | S | 2 |
| 2 . 43 | Cfo | Cfo | Η | Η | C1 | Η | S | 0 |
• · · · · · • · ·· ·· • · · · · · · 9 9 9 9 9 9 9 9 9
9 9 9 · · · · · · · · • 9 · · · · ··· ·· ·· 999 999 99 99
| Poř . č. | R5 | R6 | R7 | R8 | L | M | X | n |
| 2.44 | Cřfa | Cřfa | H | H | Cl | H | s | 2 |
| 2.45 | H | H | H | Cřfa | Cl | H | s | 0 |
| 2.46 | H | H | H | Cřfa | Cl | H | s | 2 |
| 2.47 | H | H | CH3 | ch3 | Cl | H | s | 0 |
| 2.48 | H | H | CH3 | CH3 | Cl | H | s | 2 |
| 2.49 | H | H | H | H | Cl | Cl | s | 0 |
| 2.50 | H | H | H | H | Cl | Cl | s | 2 |
| 2.51 | CH3 | CH3 | H | H | Cl | Cl | s | 0 |
| 2.52 | Cřfa | CH3 | H | H | Cl | Cl | s | 2 |
| 2.53 | H | H | H | Cřfa | Cl | Cl | s | 0 |
| 2.54 | H | H | H | CH3 | Cl | Cl | s | 2 |
| 2.55 | H | H | CH3 | Cřfa | Cl | Cl | s | 0 |
| 2.56 | H | H | CH3 | Cřfa | Cl | Cl | s | 2 |
| 2.57 | H | H | H | H | Cřfa | Cřfa | s | 0 |
| 2.58 | H | H | H | H | CH3 | Cřfa | s | 2 |
| 2.59 | CH3 | Cřfa | H | H | Cřfa | Cřfa | s | 0 |
| 2.60 | Cřfa | CH3 | H | H | Cřfa | Cřfa | s | 2 |
| 2.61 | H | H | H | CH3 | Cřfa | Cřfa | s | 0 |
| 2.62 | H | H | H | CH3 | Cřfa | Cřfa | s | 2 |
| 2.63 | H | H | CřÍ3 | Cřfa | Cřfa | Cřfa | s | 0 |
| 2.64 | H | H | CH3 | CH3 | Cřfa | Cřfa | s | 2 |
| 2-65 | H | H | H | H | Cřfa | H | S02 | 0 |
| 2.66 | H | H | H | H | Cřfa | H | SO2 | 2 |
| 2.67 | Cřfa | CH3 | H | H | Cřfa | H | SO2 | 0 |
| 2.68 | CH3 | CH3 | H | H | Cřfa | H | SO2 | 2 |
····«· Φ 9 9 9 99
9 9 9 9 9 9 · · · · ··· · · · · · 9
9 9 9 9 9 * 99 · · ·
9 9 9 9 9 9 9 9
9· 99 999 999 99 99
| Poř.č. | RS | RS | R7 | R® | L | M | X | n |
| 2.69 | Η | Η | Η | CH3 | CH3 | H | S02 | 0 |
| 2.70 | Η | Η | Η | CH3 | CH3 | H | 302 | 2 |
| 2.71 | Η | Η | CH3 | CH3 | CH3 | H | SO2 | 0 |
| 2.72 | Η | Η | CH3 | CH3 | CH3 | H | S02 | 2 |
| 2.73 | Η | Η | Η | Η | C1 | H | S02 | 0 |
| 2.74 | Η | Η | Η | Η' | C1 | H | S02 | 2 |
| 2.75 | CH3 | CH3 | Η | Η | C1 | H | SO2 | 0 |
| 2.76 | CH3 | CH3 | Η | Η | C1 | H | SO2 | 2 |
| 2.77 | Η | Η | Η | CH3 | C1 | H | S02 | 0 |
| 2.78 | Η | Η | Η | CH3 | Ci | H | SO2 | 2 |
| 2.79 | Η | Η | CH3 | CH3 | Cl | H | S02 | 0 |
| 2.80 | Η | Η | CH3 | CH3 | Cl | H | SO2 | 2 |
| 2.81 | Η | Η | Η | Η | Cl | Cl | SO2 | 0 |
| 2.82 | Η | Η | Η | Η | Cl | Cl | SO2 | 2 |
| 2.83 | CH3 | CH3 | Η | Η | Cl | Cl | SO2 | 0 |
| 2.84 | CH3 | CH3 | Η | Η | Cl | Cl | SO2 | 2 |
| 2.85 | Η | Η | Η | CH3 | Cl | Cl | SO2 | 0 |
| 2.86 | Η | Η | Η | CH3 | Cl | Cl | S02 | 2 |
| 2.87 | Η | Η | CH3 | CH3 | Cl | Cl | SO2 | 0 |
| 2.88 | Η | Η | CH3 | CH3 | Cl | Cl | SO2 | 2 |
| 2.89 | Η | Η | Η | Η | CH3 | CH3 | S02 | 0 |
| 2.90 | Η | Η | Η | Η | CH3 | CH3 | SO2 | 2 |
| 2.91 | CH3 | CH3 | Η | Η | CH3 | ch3 | S02 | 0 |
| 2.92 | CH3 | CH3 | Η | Η | CH3 | CH3 | SO2 | 2 |
| 2.93 | Η | Η | Η | CH3 | CH3 | CH3 | SO2 | 0 |
······ · · ·· · · • · · · · · · · · · · ··· · · ···· • · · · · · · ···· · • · · · · · · · · ·· ·· ··· ··· ·· ··
| Poř . č. | R5 | R6 | R7 | Ra | L | M | X | n |
| 2.94 | H | H | H | Cfc | Cfc | Cfc | SOz | 2 |
| 2.95 | H | H | Cfc | Cfc | Cfc | Cfc | SO2 | 0 |
| 2.96 | H | H | Cfc | Cfc | Cfc | Cfc | SO2 | 2 |
| Poř.č. | RS | RS | R7 | Ra | L | H | X | n |
| 10.169 | H | H | H | H | H | H | 0 | 0 |
| 10.170 | H | H | H | H | H | H | 0 | 2 |
| 10.171 | Cfc | Cfc | H | H | H | H | 0 | 0 |
| 10.172 | Cfc | Cfc | H | H | H | H | 0 | 2 |
| 10.173 | H | H | H | Cfc | H | H | 0 | 0 |
| 10.174 | H | H | H | Cfc | H | H | 0 | 2 |
| 10.175 | H | H | Cfc | Cfc | H | H | 0 | 0 |
| 10.176 | H | H | Cfc | Cfc | H | H | 0 | 2 |
| 10.177 | H | H | H | H | Cfc | H | 0 | 0 |
| 10.178 | H | H | H | H | Cfc | H | 0 | 2 |
| 10.179 | Cfc | Cfc | H | H | Cfc | H | 0 | 0 |
| 10.180 | Cfc | Cfc | H | H | Cfc | H | 0 | 2 |
| 10.181 | H | H | H | Cfc | Cfc | H | 0 | 0 |
| 10.182 | H | H | H | Cfc | Cfc | H | 0 | 2 |
| 10.183 | H | H | Cfc | Cfc | Cfc | H | 0 | 0 |
| 10.184 | H | H | Cfc | Cfc | Cfc | H | 0 | 2 |
| 10.185 | H | H | H | H | Cl | H | 0 | 0 |
·♦·· · · • · • * · ·· · · · · ··· · · · · · · • · · · · · · · · · · · ·*·· · · · · · ·· ·· ··· ··· ·· ··
| Poř.č. | RS | R6 | R7 | R.8 | L | M | X | n |
| 10.186 | H | H | H | H | Cl | H | 0 | 2 |
| 10.187 | CH3 | CH3 | H | H | Cl | H | 0 | 0 |
| 10.188 | ch3 | CH3 | H | H | Cl | H | 0 | 2 |
| 10.189 | H | H | H | ch3 | Cl | H | 0 | 0 |
| 10.190 | H | H | H | ch3 | Cl | H | 0 | 2 |
| 10.191 | H | H | CHs | CH3 | Cl | H | 0 | 0 |
| 10.192 | H | H | CH3 | ch3 | Cl | H | 0 | 2 |
| 10.193 | H | H | H | H | Cl | Cl | 0 | 0 |
| 10.194 | H | H | H | H | Cl | Cl | 0 | 2 |
| 10.195 | CH3 | CH3 | H | H | Cl | Cl | 0 | 0 |
| 10.196 | ch3 | CH3 | H | H | Cl | Cl | 0 | 2 |
| 10.197 | H | H | H | ch3 | Cl | Cl | 0 | 0 |
| 10.198 | H | H | H | CH3 | Cl | Cl | 0 | 2 |
| 10.199 | H | H | CH3 | CH3 | Cl | Cl | 0 | 0 |
| 10.200 | H | H | CH3 | ch3 | Cl | Cl | 0 | 2 |
| 10.201 | H | H | H | H | CH3 | Cto | 0 | 0 |
| 10.202 | H | H | H | H | ch3 | CH3 | 0 | 2 |
| 10.203 | CH3 | CH3 | H | H | ch3 | ch3 | 0 | 0 |
| 10.204 | CH3 | CH3 | H | H | ch3 | ch3 | 0 | 2 |
| 10.205 | CH3 | CH3 | H | CH3 | ch3 | CH3 | 0 | 0 |
| 10.206 | H | H | H | CH3 | ch3 | CH3 | 0 | 2 |
| 10.207 | H | H | CH3 | CH3 | ch3 | ch3 | 0 | 0 |
| 10.208 | H | H | ch3 | CH3 | ch3 | CH3 | 0 | 2 |
| 10.209 | H | H | H | H | N02 | H | 0 | 0 |
| 10.210 | H | H | H | H | N02 | H | 0 | 2 |
| 10.211 | CH3 | CH3 | H | H | NO2 | H | 0 | 0 |
- 36 444*44 * 4 44 44 • 4 4 ·4 44 4 44 4 • 44 4 4 4444
44 4 4 β 4444 4
4444 4 4 444
44 444 444 44 *4
| Poř.č. | R5 | R6 | R7 | RS | L | M | X | n |
| 10.212 | CH3 | CH3 | H | H | NO2 | H | 0 | 2 |
| 10.213 | H | H | H | Cřfa | NOz | H | 0 | 0 |
| 10.214 | H | H | H | CH3 | NO2 | H | 0 | 2 |
| 10.215 | H | H | Cřfa | CH3 | NO2 | H | 0 | 0 |
| 10.216 | H | H | CH3 | CH3 | NO2 | H | 0 | 2 |
| 10.217 | H | H | H | H | OCH3 | H | 0 | 0 |
| 10.218 | H | H | H | H | OCH3 | H | 0 | 2 |
| 10.219 | CH3 | CH3 | H | H | OCH3 | H | 0 | 0 |
| 10.220 | ch3 | CH3 | H | H | OCH3 | H | 0 | 2 |
| 10.221 | H | H | H | CH3 | OCH3 | H | 0 | 0 |
| 10.222 | H | H | H | CH3 | OCH3 | H | 0 | 2 |
| 10.223 | H | H | CH3 | CH3 | OCH3 | H | 0 | 0 |
| 10.224 | H | H | Cřfa | CH3 | OCH3 | H | 0 | 2 |
| 10.225 | H | H | H | H | H | H | s | 0 |
| 10.226 | H | H | H | H | H | H | s | 2 |
| 10.227 | CH3 | CH3 | H | H | H | H | s | 0 |
| 1 0.228 | CH3 | CH3 | H | H | H | H | s | 2 |
| 10.229 | H | H | H | CH3 | H | H | s | 0 |
| 10.230 | H | H | H | CH3 | H | H | s | 2 |
| 10.231 | H | H | CH3 | Cffe | H | H | s | 0 |
| 10.232 | H | H | CH3 | CH3 | H | H | s | 2 |
| 10.233 | H | H | H | H | CH3 | H | s | 0 |
| 1 0.234 | H | H | H | H | CH3 | H | s | 2 |
| 10.235 | CH3 | CH3 | H | H | CH3 | H | s | 0 |
| 10.236 | CH3 | CH3 | H | H | CH3 | H | s | 2 |
φφφφ φφ • · · φφφ • φ · · • · φ · ·· φφ • · ·· φφ • · • · • · >·» «·« ·· • · φ
Φ·· · • φ φφ ·· φ φ φ
φφ
| Poř.č. | RS | R6 | R7 | R9 | L | M | X | n |
| 10.237 | Η | Η | Η | Cfe | Cfe | H | s | 0 |
| 10.238 | Η | Η | Η | Cfe | Cfe | H | s | 2 |
| 10.239 | Η | Η | Cfe | Cfe | Cfe | H | s | 0 |
| 10.240 | Η | Η | Cfe | Cfe | Cfe | H | s | 2 |
| 10.241 | Η | Η | Η | Η | Cl | H | s | 0 |
| 10.242 | Η | Η | Η | Η | Cl | H | s | 2 |
| 10.243 | Cfe | Cfe | Η | Η | Cl | H | s | 0 |
| 10.244 | Cfe | Cfe | Η | Η | Cl | H | s | 2 |
| 10.245 | Η | Η | Η | Cfe | Cl | H | s | 0 |
| 10.246 | Η | Η | Η | Cfe | Cl | H | s | 2 |
| 10.247 | Η | Η | Cfe | Cfe | Cl | H | s | 0 |
| 10.248 | Η | Η | Cfe | Cfe | Cl | H | s | 2 |
| 10.249 | Η | Η | Η | Η | Cl | Cl | s | 0 |
| 10.250 | Η | Η | Η | Η | Cl | Cl | s | 2 |
| 10.251 | Cfe | Cfe | Η | Η | Cl | Cl | s | 0 |
| 10.252 | Cfe | Cfe | Η | Η | Cl | Cl | s | 2 |
| 10.253 | Η | Η | Η | Cfe | Cl | Cl | s | 0 |
| 10.254 | Η | Η | Η | Cfe | Cl | Cl | s | 2 |
| 1 0.255 | Η | Η | Cfe | Cfe | Cl | Cl | s | 0 |
| 10.256 | Η | Η | Cfe | Cfe | Cl | Cl | s | 2 |
| 10.257 | Η | Η | Η | Η | Cfe | Cfe | s | 0 |
| 10.258 | Η | Η | Η | Η | Cfe | Cfe | s | 2 |
| 10.259 | Cfe | Cfe | Η | Η | Cfe | Cfe | s | 0 |
| 10.260 | Cfe | Cfe | Η | Η | Cfe | Cfe | s | 2 |
| 10.261 | Η | Η | Η | Cfe | Cfe | Cfe | s | 0 |
- 38 • ·· · ·· • · · • · · · · • · · • · * ·
| Poř . č . | R5 | R6 | R7 | R3 | L | M | X | n |
| 10.262 | H | H | H | CH3 | CH3 | Cfc | s | 2 |
| 10.263 | H | H | Cfc | ch3 | ch3 | Cfc | s | 0 |
| 10.264 | H | H | Cfc | ch3 | ch3 | Cfc | s | 2 |
| 10.265 | H | H | H | H | N02 | H | s | 0 |
| 10.266 | H | H | H | H | N02 | H | s | 2 |
| 10.267 | ch3 | Cfc | H | H | NO2 | H | s | 0 |
| 10.268 | CH3 | Cfc | H | H | NO2 | H | s | 2 |
| 10.269 | H | H | H | CH3 | NO2 | H | s | 0 |
| 10.270 | H | H | H | ch3 | NO2 | H | s | 2 |
| 10.271 | H | H | Cfc | ch3 | NO2 | H | s | 0 |
| 10.272 | H | H | Cfc | ch3 | NOz | H | s | 2 |
| 10.273 | H | H | H | H | 0CH3 | H | s | 0 |
| 10.274 | H | H | H | H | och3 | H | s | 2 |
| 10.275 | CH3 | Cfc | H | H | OCfc | H | s | 0 |
| 10.276 | ch3 | ch3 | H | H | OCfc | H | s | 2 |
| 10.277 | H | H | H | CH3 | OCfc | H | s | 0 |
| 10.278 | H | H | H | ch3 | OCfc | H | s | 2 |
| 10.279 | H | H | CH3 | ch3 | OCfc | H | s | 0 |
| 10.280 | H | H | ch3 | ch3 | OCfc | H | s | 2 |
| 10.281 | H | H | H | H | H | H | SO2 | 0 |
| 10.282 | H | H | H | H | H | H | SO2 | 2 |
| 10.283 | Cfc | CH3 | H | H | H | H | SO2 | 0 |
| 10.284 | ch3 | ch3 | H | H | H | H | SO2 | 2 |
| 10.285 | H | H | H | ch3 | H | H | SO2 | 0 |
| 10.286 | H | H | H | ch3 | H | H | SO2 | 2 |
| Poř.č. | RS | RS | R7 | R8 | L | M | X | n |
| 10.287 | H | H | Cffe | CH3 | H | H | SO2 | 0 |
| 1 0.288 | H | H | CH3 | CH3 | H | H | S02 | 2 |
| 10.289 | H | H | H | H | CH3 | H | S02 | 0 |
| 10.290 | H | H | H | H | CH3 | H | S02 | 2 |
| 10.291 | CH3 | CH3 | H | H | CH3 | H | S02 | 0 |
| 10.292 | CH3 | Cffe | H | H | CH3 | H | SO2 | 2 |
| 10.293 | H | H | H | CH3 | CH3 | H | S02 | 0 |
| 1 0.294 | H | H | H | CH3 | Cffe | H | S02 | 2 |
| 10.295 | H | H | Cffe | CH3 | Cffe | H | SO2 | 0 |
| 10.296 | H | H | Cffe | CH3 | CH3 | H | SO2 | 2 |
| 10.297 | H | H | H | H | Cl | H | S02 | 0 |
| 10.298 | H | H | H | H | Cl | H | S02 | 2 |
| 10.299 | CH3 | CH3 | H | H | Cl | H | S02 | 0 |
| 10.300 | CH3 | Cffe | H | H | Cl | H | SO2 | 2 |
| 10.301 | H | H | H | Cffe | Cl | H | S02 | 0 |
| 10.302 | H | H | H | CH3 | Cl | H | SO2 | 2 |
| 10.303 | H | H | Cffe | Cffe | Cl | H | S02 | 0 |
| 10.304 | H | H | Cffe | CH3 | Cl | H | S02 | 2 |
| 10.305 | H | H | H | H | Cl | Cl | S02 | 0 |
| 10.306 | H | H | H | H | Cl | Cl | SO2 | 2 |
| 10.307 | CH3 | Cffe | H | H | Cl | Cl | SO2 | 0 |
| 10.308 | CH3 | CH3 | H | H | Cl | Cl | S02 | 2 |
| 10.309 | H | H | H | CH3 | Cl | Cl | SO2 | 0 |
| 10.310 | H | H | H | CH3 | Cl | Cl | SO2 | 2 |
| 10.311 | H | H | Cffe | CH3 | Cl | Cl | S02 | 0 |
- 40 • ·» · ·« • · « · · 'Λ ··· · ' • · »♦ 44
| Poř . č . | R5 | R6 | R7 | R8 | L | Μ | X | η |
| 10.312 | Η | Η | CH3 | Cřfc | C1 | C1 | S02 | 2 |
| 10.313 | Η | Η | Η | Η | CH3 | CHs | S02 | 0 |
| 10.314 | Η | Η | Η | Η | CH3 | CH3 | S02 | 2 |
| 10.315 | CH3 | CH3 | Η | Η | CHs | CHs | S02 | 0 |
| 10.316 | Cřfc | CH3 | Η | Η | CHs | CHs | 302 | 2 |
| 10.317 | Η | Η | Η | CH3 | CHs | CH3 | 302 | 0 |
| 10.318 | Η | Η | Η | CH3 | CHs | CH3 | S02 | 2 |
| 10.319 | Η | Η | CH3 | CH3 | CH3 | CHs | S02 | 0 |
| 10.320 | Η | Η | CH3 | CH3 | CHs | CH3 | S02 | 2 |
| 10.321 | Η | Η | Η | Η | Ν02 | Η | S02 | 0 |
| 10.322 | Η | Η | Η | Η | Ν02 | Η | 302 | 2 |
| 10.323 | CH3 | CH3 | Η | Η | Ν02 | Η | S02 | 0 |
| 10.324 | Cřfc | CH3 | Η | Η | Ν02 | Η | S02 | 2 |
| 10.325 | Η | Η | Η | CH3 | Ν02 | Η | S02 | 0 |
| 10.326 | Η | Η | Η | CH3 | ΝΟζ | Η | S02 | 2 |
| 10.327 | Η | Η | Cřfc | CH3 | ΝΟς | Η | S02 | 0 |
| 10.328 | Η | Η | CH3 | CHs | Ν02 | Η | S02 | 2 |
| 10.329 | Η | Η | Η | Η | OCHs | Η | S02 | 0 |
| 10.330 | Η | Η | Η | Η | OCHs | Η | S02 | 2 |
| 10.331 | CH3 | CH3 | Η | Η | OCHs | Η | S02 | 0 |
| 10.332 | CH3 | CH3 | Η | Η | OCHs | Η | S02 | 2 |
| 10.333 | Η | Η | Η | CH3 | 0CH3 | Η | S02 | 0 |
| 10.334 | Η | Η | Η | CH3 | OCHs | Η | 302 | 2 |
| 10.335 | Η | Η | CH3 | CHs | 0CH3 | Η | S02 | 0 |
| 10.336 | Η | Η | CH3 | CH3 | OCHs | Η | S02 | 2 |
·· · · • · β · · ·«·· • · ·· · 9 · ···· ·
9 9 9 9 9 9 9 ·· >· ««« ··· *·
-41Tabulka 4
(%
| Poř.č. | RS | RS | R7 | R8 | L | M | X | n |
| 4.97 | H | H | H | H | CH | H | 0 | 0 |
| 4.98 | H | H | H | H | CH3 | H | 0 | 2 |
| 4.99 | ch3 | Cto | H | H | ch3 | H | 0 | 0 |
| 4.100 | ch3 | CH3 | H | H | ch3 | H | 0 | 2 |
| 4.101 | H | H | H | ch3 | ch3 | H | 0 | 0 |
| 4.102 | H | H | H | ch3 | ch3 | H | 0 | 2 |
| 4.103 | H | H | ch3 | ch3 | ch3 | H | 0 | 0 |
| 4.104 | H | H | ch3 | ch3 | ch3 | H | 0 | 2 |
| 4.105 | H | H | H | H | Cl | H | 0 | 0 |
| 4.106 | H | H | H | H | Cl | H | 0 | 2 |
| 4.107 | CH3 | Cřfa | H | H | Cl | H | 0 | 0 |
| 4.108 | ch3 | CH3 | H | H | Cl | H | 0 | 2 |
| 4.109 | H | H | H | H | Cl | H | 0 | 0 |
| 4.110 | H | H | H | CH3 | Cl | H | 0 | 2 |
| 4.111 | H | H | CH3 | ch3 | Cl | H | 0 | 0 |
| 4.112 | H | H | ch3 | ch3 | Cl | H | 0 | 2 |
| 4.113 | H | H | H | H | Cl | Cl | 0 | 0 |
| 4.114 | H | H | H | H | Cl | Cl | 0 | 2 |
| 4.115 | ch3 | CH3 | H | H | Cl | Cl | 0 | 0 |
| 4.116 | ch3 | ch3 | H | H | Cl | Cl | 0 | 2 |
| 4.117 | H | H | H | CH3 | Cl | Cl | 0 | 0 |
• 9 ·· ·9 • · · 9 * · 9 • · » · · ···» • · 9 · · · 9 ·· 9 · · ••99 · · » · » • 9 ·* *9 · ··· ··
| Poř . č. | R5 | R6 | R7 | R8 | L | M | X | n |
| 4.118 | H | H | H | Cřij | Cl | Cl | 0 | 2 |
| 4.119 | H | H | ch3 | CH3 | Cl | Cl | 0 | 0 |
| 4.120 | H | H | ch3 | ch3 | Cl | Cl | 0 | 2 |
| 4.121 | H | H | H | H | CH3 | ch3 | 0 | 0 |
| 4.122 | H | H | H | H | ch3 | ch3 | 0 | 2 |
| 4.123 | ch3 | CH3 | H | H | Cto | ch3 | 0 | 0 |
| 4.124 | CH3 | ch3 | H | H | CH3 | ch3 | 0 | 2 |
| 4.125 | H | H | H | CH3 | ch3 | ch3 | 0 | 0 |
| 4.126 | H | H | H | ch3 | ch3 | ch3 | 0 | 2 |
| 4.127 | H | H | CH3 | CH3 | ch3 | ch3 | 0 | 0 |
| 4.128 | H | H | CH3 | ch3 | ch3 | CH3 | 0 | 2 |
| 4.129 | H | H | H | H | ch3 | H | s | 0 |
| 4.130 | H | H | H | H | ch3 | H | s | 2 |
| 4.131 | CH3 | CH3 | H | H | ch3 | H | s | 0 |
| 4.132 | CH3 | ch3 | H | H | ch3 | H | s | 2 |
| 4.133 | H | H | H | ch3 | ch3 | H | s | 0 |
| 4.134 | H | H | H | ch3 | ch3 | H | s | 2 |
| 4.135 | H | H | ch3 | ch3 | ch3 | H | s | 0 |
| 4.136 | H | H | ch3 | Cte | ch3 | H | s | 2 |
| 4.137 | H | H | H | H | Cl | H | s | 0 |
| 4.138 | H | H | H | H | Cl | H | s | 2 |
| 4.139 | ch3 | ch3 | H | H | Cl | H | s | 0 |
| 4.140 | ch3 | ch3 | H | H | Cl | H | s | 2 |
| 4.141 | H | H | H | ch3 | Cl | H | s | 0 |
| 4.142 | H | H | H | ch3 | Cl | H | s | 2 |
• · « · • ·
| Poř . č . | R5 | R6 | R7 | RS | L | M | X | n |
| 4.143 | H | H | CH3 | CH3 | Cl | H | s | 0 |
| 4.144 | H | H | CH3 | CH3 | Cl | Cl | s | 2 |
| 4.145 | H | H | H | H | Ci | Cl | s | 0 |
| 4.146 | H | H | H | H | Cl | Cl | s | 2 |
| 4.147 | CHs | CH3 | H | H | Cl | Cl | s | 0 |
| 4.148 | CH3 | CH3 | H | H | Cl | Cl | s | 2 |
| 4.149 | H | H | H | CH3 | Cl | Cl | s | 0 |
| 4.150 | H | H | H | CH3 | Cl | Cl | s | 2 |
| 4.151 | H | H | ch3 | CH | Cl | Cl | s | 0 |
| 4.152 | H | H | ch3 | CH3 | Cl | Cl | s | 2 |
| 4.153 | H | H | H | H | CH3 | CH3 | s | 0 |
| 4.154 | H | H | H | H | ch3 | ch3 | s | 2 |
| 4.155 | CH3 | ch3 | H | H | CH3 | CH3 | s | 0 |
| 4.156 | CH3 | CH3 | H | H | CH3 | CH3 | s | 2 |
| 4.157 | H | H | H | CH3 | ch3 | CH3 | s | 0 |
| 4.158 | H | H | H | ch3 | CH3 | CH3 | s | 2 |
| 4.159 | H | H | CHs | CH3 | ch3 | CH3 | s | 0 |
| 4.160 | H | H | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 4.161 | H | H | H | H | ch3 | H | so? | 0 |
| 4.162 | H | H | H | H | CH3 | H | so? | 2 |
| 4.163 | CH3 | CH3 | H | H | ch3 | H | so? | 0 |
| 4.164 | ch3 | CH3 | H | H | ch3 | H | so? | 2 |
| 4.165 | H | H | H | CH3 | CH3 | H | so? | 0 |
| 4.166 | H | H | H | CH3 | CH3 | H | so? | 2 |
| 4.167 | H | H | CH3 | CH3 | ch3 | H | so? | 0 |
| P o ř . č . | RS | R6 | R7 | RQ | L | M | X | n |
| 4.168 | H | H | CH3 | ch3 | CH3 | H | S02 | 2 |
| 4.169 | H | H | H | H | Cl | H | S02 | 0 |
| 4.170 | H | H | H | H | Cl | H | SO2 | 2 |
| 4.171 | ch3 | ch3 | H | H | Cl | H | S02 | 0 |
| 4.172 | ch3 | ch3 | H | H | Cl | H | S02 | 2 |
| 4.173 | H | H | H | CH3 | Cl | H | S02 | 0 |
| 4.174 | H | H | H | ch3 | Cl | H | SO2 | 2 |
| 4.175 | H | H | CFfa | ch3 | Cl | H | SO2 | 0 |
| 4.176 | H | H | Cřfa | ch3 | Cl | H | SO2 | 2 |
| 4.177 | H | H | H | H | Cl | Cl | SO2 | 0 |
| 4.178 | H | H | H | H | Cl | Cl | S02 | 2 |
| 4.179 | Cřfa | ch3 | H | H | Cl | Cl | S02 | 0 |
| 4.180 | ch3 | ch3 | H | H | Cl | Cl | S02 | 2 |
| 4.181 | H | H | H | ch3 | Cl | Cl | S02 | 0 |
| 4.182 | H | H | H | ch3 | Cl | Ci | SO2 | 2 |
| 4.183 | H | H | ch3 | ch3 | Cl | Cl | SO2 | 0 |
| 4.184 | H | H | ch3 | ch3 | Cl | Cl | SO2 | 2 |
| 4.185 | H | H | H | H | CH3 | ch3 | S02 | 0 |
| 4.186 | H | H | H | H | CPb | ch3 | SO2 | 2 |
| 4.187 | ch3 | ch3 | H | H | ch3 | ch3 | SO2 | 0 |
| 4.188 | ch3 | ch3 | H | H | CHs | ch3 | S02 | 2 |
| 4.189 | H | H | H | CH3 | ch3 | ch3 | S02 | 0 |
| 4.190 | H | H | H | ch3 | ch3 | Cfc | SO2 | 2 |
| 4.191 | H | H | ch3 | ch3 | ch3 | ch3 | SO2 | 0 |
| 4.192 I | H | H | ch3 | ch3 | ch3 | H | 302 | 2 |
Tabulka 5
• · · · «♦ · · ι • · a ♦ · · ·
| 1 P o ř . č . | 1- R5 | R6 | R7 | RS | Rl | R2 | R3 | R4 | M | 1- L | X | n |
| 5 . 1 | H | H | H | H | H | H | Cfc | H | H | H | 0 | 0 |
| 5.2 | H | H | H | H | H | H | Cfc | H | H | H | 0 | 2 |
| 5.3 | Cfc | Cfc | H | H | H | Ή | Cfc | H | H | H | 0 | 0 |
| 5.4 | Cfc | Cfc | H | H | H | H | Cfc | H | H | H | 0 | 2 |
| 5.5 | H | H | H | Cfc | H | H | Cfc | H | H | H | 0 | 0 |
| 5.6 | H | H | H | Cfc | H | H | Cfc | H | H | H | 0 | 2 |
| 5.7 | H | H | Cfc | Cfc | H | H | Cfc | H | H | H | 0 | 0 |
| 5.8 | H | H | Cfc | Cfc | H | H | Cfc | H | H | H | 0 | 2 |
| 5.9 | H | H | H | H | H | H | Cfc | H | Cfc | H | 0 | 0 |
| 5.10 | H | H | H | H | H | H | Cfc | H | Cfc | H | 0 | 2 |
| 5.11 | Cfc | Cfc | H | H | H | H | Cfc | H | Cfc | H | 0 | 0 |
| 5.12 | Cfc | Cfc | H | H | H | H | Cfc | H | Cfc | H | 0 | 2 |
| 5.13 | H | H | H | Cfc | H | H | Cfc | H | Cfc | H | 0 | 0 |
| 5.14 | H | H | H | Cfc | H | H | Cfc | H | Cfc | H | 0 | 2 |
| 5.15 | H | H | Cfc | Cfc | H | H | Cfc | H | Cfc | H | 0 | 0 |
| 5.16 | H | H | Cfc | Cfc | H | H | Cfc | H | Cfc | H | 0 | 2 |
| 5.17 | H | H | H | H | H | H | Cfc | H | Cl | H | 0 | 0 |
| 5.18 | H | H | H | H | H | H | Cfc | H | Cl | H | 0 | 2 |
| 5.19 | Cfc | Cfc | H | H | H | H | Cfc | H | Cl | H | 0 | 0 |
| 5.20 | Cfc | Cfc | H | H | H | H | Cfc | H | Cl | H | 0 | 2 |
| 5.2 1 | H | H | H | Cfc | H | H | Cfc | H | Cl | H | 0 | 0 |
| 5.22 | H | H | H | Cfc | H | H | Cfc | H | Cl | H | 0 | 2 |
- 46 • 00 0 0 * 0 » 0 0 0 0
0 0 0 0 «· 00 000 000
0 0 «0·0 0
0 0 • » ·0
| 1-—— P o ř . č . | RS | RS | R7 | R8 | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.23 | H | H | CH3 | CH | H | H | CH.3 | H | Cl | H | 0 | 0 |
| 5.24 | H | H | CH3 | CH3 | H | H | ch3 | H | Cl | H | 0 | 2 |
| 5.25 | H | H | H | H | H | H | ch3 | H | Cl | H | 0 | 0 |
| 5.26 | H | H | H | H | H | H | CH3 | H | Cl | Cl | 0 | 2 |
| 5.27 | CH3 | CH3 | H | H | H | H | ch3 | H | Cl | CI | 0 | 0 |
| 5.28 | CH3 | CH3 | H | H | H | Ή | ch3 | H | Cl | Cl | 0 | 2 |
| 5.29 | H | H | H | CH3 | H | H | ch3 | H | Cl | Cl | 0 | 0 |
| 5.30 | H | H | H | CH3 | H | H | ch3 | H | Cl | Cl | 0 | 2 |
| 5.31 | H | H | ch3 | ch3 | H | H | ch3 | H | Cl | Cl | 0 | 0 |
| 5.32 | H | H | CH3 | ch3 | H | H | ch3 | H | Cl | Cl | 0 | 2 |
| 5.33 | H | H | H | H | H | H | ch3 | H | ch3 | ch3 | 0 | 0 |
| 5.34 | H | H | H | H | H | H | CH3 | H | ch3 | ch3 | 0 | 2 |
| 5.35 | CH3 | CH3 | H | H | H | H | CH3 | H | ch3 | ch3 | 0 | 0 |
| 5.36 | CH3 | CH3 | H | H | H | H | ch3 | H | ch3 | ch3 | 0 | 2 |
| 5.37 | H | H | H | ch3 | H | H | ch3 | H | ch3 | CH3 | 0 | 0 |
| 5.38 | H | H | H | ch3 | H | H | CH3 | H | ch3 | ch3 | 0 | 2 |
| 5.39 | H | H | CH3 | ch3 | H | H | ch3 | H | ch3 | ch3 | 0 | 0 |
| 5.40 | H | H | CH3 | ch3 | H | H | CH3 | H | CH3 | ch3 | 0 | 2 |
| 5.41 | H | H | H | H | H | H | ch3 | H | och3 | H | 0 | 0 |
| 5.42 | H | H | H | H | H | H | ch3 | H | och3 | H | 0 | 2 |
| 5.43 | CH3 | CH3 | H | H | H | H | ch3 | H | och3 | H | 0 | 0 |
| 5.44 | ch3 | CH3 | H | H | H | H | ch3 | H | och3 | H | 0 | 2 |
| 5.45 | H | H | H | CH3 | H | H | ch3 | H | och3 | H | 0 | 0 |
| 5.46 | H | H | H | ch3 | H | H | ch3 | H | och3 | H | 0 | 2 |
| 5.47 | H I | H | CH3 | ch3 | H | H | ch3 | H | och3 | H _ | 0 | 0 _l |
- 47 ·· · * ι« *« · · 4 • · 1 • · · *
| Poř.č. | R5 | R6 | R7 | R8 | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.48 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | OCffa | H | 0 | 2 |
| 5.49 | H | H | H | H | H | H | Cřfa | H | H | H | s | 0 |
| 5.50 | H | H | H | H | H | H | Cřfa | H | H | H | s | 2 |
| 5.51 | ch3 | Cřfa | H | H | H | H | Cřfa | H | H | H | s | 0 |
| 5.52 | Cřfa | Cřfa | H | H | H | H | Cřfa | H | H | H | s | 2 |
| 5.53 | H | H | H | Cřfa | H | .H | Cřfa | H | H | H | s | 0 |
| 5.54 | H | H | H | Cřfa | H | H | Cřfa | H | H | H | s | 2 |
| 5.55 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | H | H | s | 0 |
| 5.56 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | H | H | s | 2 |
| 5.57 | H | H | H | H | H | H | Cřfa | H | Cřfa | H | s | 0 |
| 5.58 | H | H | H | H | H | H | Cřfa | H | Cřfa | H | s | 2 |
| 5.59 | Cřfa | Cřfa | H | H | H | H | Cřfa | H | Cřfa | H | s | 0 |
| 5.60 | Cřfa | Cřfa | H | H | H | H | Cřfa | H | Cřfa | H | s | 2 |
| 5.61 | H | H | H | Cřfa | H | H | Cřfa | H | Cřfa | H | s | 0 |
| 5.62 | H | H | H | Cřfa | H | H | Cřfa | H | CH3 | H | s | 2 |
| 5.63 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | Cřfa | H | s | 0 |
| 5.64 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | Cřfa | H | s | 2 |
| 5.65 | H | H | H | H | H | H | Cřfa | H | Cl | H | s | 0 |
| 5.66 | H | H | H | H | H | H | Cřfa | H | Cl | H | s | 2 |
| 5.67 | Cřfa | Cřfa | H | H | H | H | Cřfa | H | Cl | H | s | 0 |
| 5.68 | Cřfa | CH3 | H | H | H | H | Cřfa | H | Cl | H | s | 2 |
| 5.69 | H | H | H | Cřfa | H | H | Cřfa | H | Cl | H | s | 0 |
| 5.70 | H | H | H | Cřfa | H | H | Cřfa | H | Cl | H | s | 2 |
| 5.71 | H | H | Cřfa | Cřfa | H | H | Cřfa | H | Cl | H | s | 0 |
| 5.72 _ | H | H | Cřfa | Cřfa | H | H | Cřfa | H | Cl | H | s _ | 2 |
- 48 ·· · · 4 • · « « · · »
| Poř.č. | R5 | R6 | R7 | R® | R1 | R2 | R3 | R4 | M | L | X | n |
| 5.73 | H | H | H | H | H | H | CH3 | H | Cl | Cl | S | 0 |
| 5.74 | H | H | H | H | H | H | CHs | H | Cl | Cl | s | 2 |
| 5.75 | CH3 | CHs | H | H | H | H | CH3 | H | Cl | Cl | s | 0 |
| 5.76 | CH3 | CHs | H | H | H | H | CH3 | H | Cl | Cl | s | 2 |
| 5.77 | H | H | H | CH3 | H | H | CH3 | H | Cl | Cí | s | 0 |
| 5.78 | H | H | H | CHs | H | H | CH3 | H | Cl | Cl | s | 2 |
| 5.79 | H | H | CHs | CH3 | H | H | CHs | H | Cl | Cl | s | 0 |
| 5.80 | H | H | CHs | CH3 | H | H | CHs | H | Cl | Cl | s | 2 |
| 5.81 | H | H | H | H | H | H | CH3 | H | ch3 | CH3 | s | 0 |
| 5.82 | H | H | H | H | H | H | ch3 | H | CHs | CHs | s | 2 |
| 5.83 | CHs | CHs | H | H | H | H | CH3 | H | ch3 | CH3 | s | 0 |
| 5.84 | CH3 | CHs | H | H | H | H | CHs | H | ch3 | CHs | s | 2 |
| 5.85 | H | H | H | CHs | H | H | ch3 | H | ch3 | CHs | s | 0 |
| 5.86 | H | H | H | CH3 | H | H | ch3 | H | CHs | CHs | s | 2 |
| 5.87 | H | H | ch3 | ch3 | H | H | CH3 | H | CH3 | CH3 | s | 0 |
| 5.88 | H | H | CHs | CH3 | H | H | CH3 | H | CHs | CH3 | s | 2 |
| 5.89 | H | H | H | H | H | H | CHs | H | OCHs | H | s | 0 |
| 5.90 | H | H | H | H | H | H | CHs | H | 0CH3 | H | s | 2 |
| 5.91 | CHs | CH3 | H | H | H | H | ch3 | H | OCHs | H | s | 0 |
| 5.92 | ch3 | CH3 | H | H | H | H | CH3 | H | OCHs | H | s | 2 |
| 5.93 | H | H | H | CHs | H | H | CHs | H | OCH3 | H | s | 0 |
| 5.94 | H | H | H | CH3 | H | H | CHs | H | 0CH3 | H | s | 2 |
| 5.95 | H | H | CHs | CHs | H | H | ch3 | H | OCHs | H | s | 0 |
| 5.96 | H | H | CHs | CH3 | H | H | CHs | H | OCHs | H | s | 2 |
| 5.97 | H | H | H | H | H | H | CH3 | H | 0CH3 | H | SO2 | 0 |
- 49 • ··» · ·
| Poř.č. | Rs | RS | R7 | R® | Ri | R2 | RS | R4 | M | 1- L | X | n |
| 5.98 | H | H | H | H | H | H | Cfe | H | H | H | so? | 2 |
| 5.99 | Cfe | Cfe | H | H | H | H | Cfe | H | H | H | so? | 0 |
| 5.100 | Cfe | Cfe | H | H | H | H | Cfe | H | H | H | so? | 2 |
| 5.101 | H | H | H | Cfe | H | H | Cfe | H | H | H | S02 | 0 |
| 5.102 | H | H | H | Cfe | H | H | Cfe | H | H | H | SO2 | 2 |
| 5.103 | H | H | Cfe | Cfe | H | H | Cfe | H | H | H | so? | 0 |
| 5.104 | H | H | Cfe | Cfe | H | H | Cfe | H | H | H | so? | 2 |
| 5.105 | H | H | H | H | H | H | Cfe | H | Cfe | H | so? | 0 |
| 5.106 | H | H | H | H | H | H | Cfe | H | Cfe | H | S02 | 2 |
| 5.107 | Cfe | Cfe | H | H | H | H | Cfe | H | Cfe | H | S02 | 0 |
| 5.108 | Cfe | Cfe | H | H | H | H | Cfe | H | Cfe | H | SO2 | 2 |
| 5.109 | H | H | H | Cfe | H | H | Cfe | H | Cfe | H | so? | 0 |
| 5.110 | H | H | H | Cfe | H | H | Cfe | H | Cfe | H | so? | 2 |
| 5.111 | H | H | Cfe | Cfe | H | H | Cfe | H | Cfe | H | so? | 0 |
| 5.112 | H | H | Cfe | Cfe | H | H | Cfe | H | Cfe | H | so? | 2 |
| 5.113 | H | H | H | H | H | H | Cfe | H | Cl | H | so? | 0 |
| 5.114 | H | H | H | H | H | H | Cfe | H | Cl | H | so? | 2 |
| 5.115 | Cfe | Cfe | H | H | H | H | Cfe | H | Cl | H | so? | 0 |
| 5.116 | Cfe | Cfe | H | H | H | H | Cfe | H | Cl | H | so? | 2 |
| 5.117 | H | H | H | Cfe | H | H | Cfe | H | Cl | H | S02 | 0 |
| 5.118 | H | H | H | Cfe | H | H | Cfe | H | Cl | H | so? | 2 |
| 5.119 | H | H | Cfe | Cfe | H | H | Cfe | H | Cl | H | so? | 0 |
| 5.120 | H | H | Cfe | Cfe | H | H | Cfe | H | Cl | H | so? | 2 |
| 5.121 | H | H | H | H | H | H | Cfe | H | Cl | Cl | so? | 0 |
| 5.122 | H | H | H | H | H | H | Cfe | H | Cl | Cl | so? | 2 |
- 50 *· · · · • · * • · · *
| Poř . č . | R5 | R6 | R.7 | R3 | RA | R2 | R3 | R4 | M | L | X | n |
| 5.123 | CH3 | ch3 | H | H | H | H | ch3 | H | Cl | Cl | SO2 | 0 |
| 5.124 | ch3 | ch3 | H | H | H | H | ch3 | H | Cl | Cl | SO2 | 2 |
| 5.125 | H | H | H | ch3 | H | H | CPb | H | Cl | Cl | SO2 | 0 |
| 5.126 | H | H | H | ch3 | H | H | CPb | H | Cl | Cl | SO2 | 2 |
| 5.127 | H | H | ch3 | ch3 | H | H | CH3 | H | Cl | Cl | SO2 | 0 |
| 5.128 | H | H | ch3 | ch3 | H | H | ch3 | H | Cl | Cl | SO2 | 2 |
| 5.129 | H | H | H | H | H | H | ch3 | H | CPb | CH3 | SO2 | 0 |
| 5.130 | H | H | H | H | H | H | CPb | H | ch3 | CPb | SO2 | 2 |
| 5.131 | CH3 | ch3 | H | H | H | H | CPfa | H | CPb | CPb | SO2 | 0 |
| 5.132 | CH3 | CPb | H | H | H | H | ch3 | H | CPb | CPb | SO2 | 2 |
| 5.133 | H | H | H | ch3 | Pí | H | ch3 | H | CPb | CPb | SO2 | 0 |
| 5.134 | Pí | Pí | H | CPb | H | H | CPb | H | CPb | CPb | SO2 | 2 |
| 5.135 | H | H | CH3 | CH3 | H | H | CPb | H | CPb | CPb | SO2 | 0 |
| 5.136 | H | H | ch3 | ch3 | H | H | ch3 | H | CH3 | CPb | SO2 | 2 |
| 5.137 | H | H | H | H | H | H | CPb | CPb | H | H | 0 | 0 |
| 5.138 | H | H | H | H | H | H | CPb | CPb | H | H | 0 | 2 |
| 5.139 | CH3 | ch3 | H | H | H | H | CPb | CPb | H | H | 0 | 0 |
| 5.140 | ch3 | ch3 | H | H | H | H | ch3 | CPb | H | H | 0 | 2 |
| 5.141 | H | H | H | ch3 | H | H | ch3 | CPb | H | H | 0 | 0 |
| 5.142 | H | H | H | ch3 | H | H | CPb | CPb | H | H | 0 | 2 |
| 5.143 | H | H | ch3 | ch3 | H | H | CPb | CPb | H | H | 0 | 0 |
| 5.144 | H | H | ch3 | ch3 | H | H | CPb | CPb | H | H | 0 | 2 |
| 5.145 | H | H | H | H | H | H | CPb | CPb | CPb | H | 0 | 0 |
| 5.146 | H | H | H | H | H | H | CPb | CPb | ch3 | H | 0 | 2 |
| 5.147 | CH3 | ch3 | H | H | H | H | CPb | CPb | CPb | H | 0 | 0 |
- 51 * · · • · · 8 9 * · · « > * *·· · · 9 9 99 * · ·· · 9 9 ·« 9 9 · *·· · · 9 · · * · * * 9 Λ 9 ·«· « · « ·
| Poř.č. | RS | R.6 | R7 | R8 | R.1 | R.2 | R3 | R4 | Μ | L | X | η |
| 5.148 | CH3 | ch3 | Η | Η | Η | Η | CHs | CHs | CH3 | Η | 0 | 2 |
| 5.149 | Η | Η | Η | CHs | Η | Η | CHs | CH3 | CH3 | Η | 0 | 0 |
| 5.150 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | CHs | Η | 0 | 2 |
| 5.151 | Η | Η | CH3 | CHs | Η | Η | CHs | CH3 | CH3 | Η | 0 | 0 |
| 5.152 | Η | Η | CH3 | CHs | Η | Η | CHs | CHs | CHs | Η | 0 | 2 |
| 5.153 | Η | Η | Η | Η | Η | Ή | CHs | CHs | C1 | Η | 0 | 0 |
| 5.154 | Η | Η | Η | Η | Η | Η | CHs | CHs | C1 | Η | 0 | 2 |
| 5.155 | CH3 | CH3 | Η | Η | Η | Η | CHs | CH3 | C1 | Η | 0 | 0 |
| 5.156 | CH3 | CH3 | Η | Η | Η | Η | CHs | CH3 | C1 | Η | 0 | 2 |
| 5.157 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | C1 | Η | 0 | 0 |
| 5.158 | Η | Η | Η | CH3 | Η | Η | CHs | CHs | C1 | Η | 0 | 2 |
| 5.159 | Η | Η | CH3 | CH3 | Η | Η | CHs | CH3 | C1 | Η | 0 | 0 |
| 5.160 | Η | Η | CH3 | CH3 | Η | Η | CHs | CH3 | C1 | Η | 0 | 2 |
| 5.161 | Η | Η | Η | Η | Η | Η | CHs | CH3 | C1 | C1 | 0 | 0 |
| 5.162 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | C1 | C1 | 0 | 2 |
| 5.163 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | C1 | C1 | 0 | 0 |
| 5.164 | CH3 | CHs | Η | Η | Η | Η | CH3 | CHs | C1 | C1 | 0 | 2 |
| 5.165 | Η | Η | Η | CHs | Η | Η | CHs | CH3 | C1 | C 1 | 0 | 0 |
| 5.166 | Η | Η | Η | CHs | Η | Η | CH3 | CHs | C1 | C1 | 0 | 2 |
| 5.167 | Η | Η | CH3 | CHs | Η | Η | CHs | CHs | C1 | C1 | 0 | 0 |
| 5.168 | Η | Η | CH3 | CHs | Η | Η | CH3 | CH3 | C1 | C1 | 0 | 2 |
| 5.169 | Η | Η | Η | Η | Η | Η | CHs | CHs | CH3 | CH3 | 0 | 0 |
| 5.170 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | CH3 | 0 | 2 |
| 5.171 | CH3 | CHs | Η | Η | Η | Η | CH3 | CH3 | CH3 | CHs | 0 | 0 |
| 5.172 | CH3 | CHs | Η | Η | Η | Η | CH3 | CH3 | CHs | CHs | 0 | 2 |
- 52 • · · · • · · • ·· • · · · · • · · « · · ·
| Poř.č. | RS | RS | R7 | RS | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.173 | H | H | H | Cfo | H | H | Cfo | Cfo | Cfo | Cfo | 0 | 0 |
| 5.174 | H | H | H | Cfo | H | H | Cfo | Cfo | Cfo | Cfo | 0 | 2 |
| 5.175 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | Cfo | Cfo | 0 | 0 |
| 5.176 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | Cfo | Cfo | 0 | 2 |
| 5.177 | H | H | H | H | H | H | Cfo | Cfo | OCfo | H | 0 | 0 |
| 5.178 | H | H | H | H | H | H | Cfo | Cfo | OCfo | H | 0 | 2 |
| 5.179 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | OCfo | H | 0 | 0 |
| 5.180 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | OCfo | H | 0 | 2 |
| 5.18 1 | H | H | H | Cfo | H | H | Cfo | Cfo | OCfo | H | 0 | 0 |
| 5.182 | H | H | H | Cfo | H | H | Cfo | Cfo | OCfo | H | 0 | 2 |
| 5.183 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | OCfo | H | 0 | 0 |
| 5.184 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | OCfo | H | 0 | 2 |
| 5.185 | H | H | H | H | H | H | Cfo | Cfo | H | H | s | 0 |
| 5.186 | H | H | H | H | H | H | Cfo | Cfo | H | H | s | 2 |
| 5.187 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | H | H | s | 0 |
| 5. 188 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | H | H | s | 2 |
| 5.189 | H | H | H | Cfo | H | H | Cfo | Cfo | H | H | s | 0 |
| 5.190 | H | H | H | Cfo | H | H | Cfo | Cfo | H | H | s | 2 |
| 5.191 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | H | H | s | 0 |
| 5.192 | H | H | Cfo | Cfo | H | H | Cfo | Cfo | H | H | s | 2 |
| 5.193 | H | H | H | H | H | H | Cfo | Cfo | Cfo | H | s | 0 |
| 5.194 | H | H | H | H | H | H | Cfo | Cfo | Cfo | H | s | 2 |
| 5.195 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | Cfo | H | s | 0 |
| 5.196 | Cfo | Cfo | H | H | H | H | Cfo | Cfo | Cfo | H | s | 2 |
| 5.197 | H | H | H | Cfo | H | H | Cfo | Cfo | Cfo | H | s | 0 |
| Ρ ο ř . č . | RS | R6 | R7 | R® | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.198 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | CH3 | H | s | 2 |
| 5.199 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | CH3 | H | s | 0 |
| 5.200 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | CH3 | H | s | 2 |
| 5.201 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | Cl | H | s | 0 |
| 5.202 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | Cl | H | s | 2 |
| 5.203 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | H | s | 0 |
| 5.204 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | H | s | 2 |
| 5.205 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | Cl | H | s | 0 |
| 5.206 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | Cl | H | s | 2 |
| 5.207 | Η | Η | CH3 | CH3 | Η | Η | CH3 | ch3 | Cl | H | s | 0 |
| 5.208 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | Cl | H | s | 2 |
| 5.209 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | Cl | Cl | s | 0 |
| 5.210 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | Cl | Cl | s | 2 |
| 5.211 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | Cl | s | 0 |
| 5.212 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | Cl | s | 2 |
| 5.213 | Η | Η | Η | CH3 | Η | Η | Ctts | CH3 | Cl | Cl | s | 0 |
| 5.214 | Η | Η | Η | CH3 | Η | Η | CH3 | ch3 | Cl | Cl | s | 2 |
| 5.215 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | Cl | Cl | s | 0 |
| 5.216 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | Cl | C 1 | s | 2 |
| 5.217 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | CH3 | s | 0 |
| 5.218 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 5.219 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | ch3 | CH3 | s | 0 |
| 5.220 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 5.221 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | CH3 | CH3 | s | 0 |
| 5.222 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | CH3 | ch3 | s | 2 |
- 54 • · · · · · • · · · · ·· 9 9 9 9
9 9 9 9 9 9 99
9 9 9 9 9 9 99 · 9 ·
9 9 · · · · · ·
99 999 999 99 99
| Poř . č. | RS | R6 | R7 | RS | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.223 | H | H | CH3 | CH3 | H | H | CH3 | CH3 | CH3 | H | s | 0 |
| 5.224 | H | H | CH3 | CH3 | H | H | ch3 | CH3 | CH3 | H | s | 2 |
| 5.225 | H | H | H | H | H | H | CH3 | CH3 | 0CH3 | H | s | 0 |
| 5.226 | H | H | H | H | H | H | CH3 | CH3 | OCH3 | H | s | 2 |
| 5.227 | CH3 | CH3 | H | H | H | H | CH3 | CH3 | 0CH3 | H | s | 0 |
| 5.228 | ch3 | ch3 | H | H | H | H | CH3 | CH3 | 0CH3 | H | s | 2 |
| 5.229 | H | H | H | CH3 | H | H | CH3 | ch3 | 0CH3 | H | s | 0 |
| 5.230 | H | H | H | ch3 | H | H | CH3 | CH3 | 0CH3 | H | s | 2 |
| 5.231 | H | H | ch3 | CH3 | H | H | CH3 | ch3 | OCH3 | H | s | 0 |
| 5.232 | H | H | ch3 | CH3 | H | H | CH3 | CH3 | 0CH3 | H | s | 2 |
| 5.233 | H | H | H | H | H | H | ch3 | CH3 | H | H | S02 | 0 |
| 5.234 | H | H | H | H | H | H | CH3 | CH3 | H | H | S02 | 2 |
| 5.235 | CH3 | CH3 | H | H | H | H | CH3 | ch3 | H | H | SO2 | 0 |
| 5.236 | ch3 | ch3 | H | H | H | H | CH3 | CH3 | H | H | SO2 | 2 |
| 5.237 | H | H | H | ch3 | H | H | CH3 | ch3 | H | H | S02 | 0 |
| 5.238 | H | H | H | CH3 | H | H | CH3 | CH3 | H | H | SO2 | 2 |
| 5.239 | H | H | CH3 | ch3 | H | H | ch3 | CH3 | H | H | S02 | 0 |
| 5.240 | H | H | ch3 | ch3 | H | H | CH3 | CH3 | H | H | S02 | 2 |
| 5.241 | H | H | H | H | H | H | CH3 | ch3 | CH3 | H | S02 | 0 |
| 5.242 | H | H | H | H | H | H | CH3 | ch3 | CH3 | H | SO2 | 2 |
| 5.243 | CH3 | CH3 | H | H | H | H | CH3 | CH3 | ch3 | H | S02 | 0 |
| 5.244 | CH3 | ch3 | H | H | H | H | CH3 | CH3 | ch3 | H | SO2 | 2 |
| 5.245 | H | H | H | CH3 | H | H | CH3 | CH3 | CH3 | H | S02 | 0 |
| 5.246 | H | H | H | CH3 | H | H | CH3 | CH3 | CH3 | H | SO2 | 2 |
| 5.247 | H | H | CH3 | ch3 | H | H | CH3 | CH3 | CH3 | H | so? | 0 |
| Poř.č. | R5 | R6 | R7 | R9 | R1 | R2 | R3 | R4 | M | L | X | n |
| 5.248 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CH3 | CH3 | H | S02 | 2 |
| 5.249 | Η | Η | Η | Η | Η | Η | CH3 | CHs | Cl | H | SO2 | 0 |
| 5.250 | Η | Η | Η | Η | Η | Η | CHs | ch3 | Cl | H | SO2 | 2 |
| 5.251 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | H | SO2 | 0 |
| 5.252 | ch3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | Cl | H | S02 | 2 |
| 5.253 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | Cl | H | SO2 | 0 |
| 5.254 | Η | Η | Η | CH3 | Η | Η | CH3 | CHs | Cl | H | SO2 | 2 |
| 5.255 | Η | Η | ch3 | CH3 | Η | Η | CH3 | CH3 | Cl | H | SO2 | 0 |
| 5.256 | Η | Η | CH3 | CH3 | Η | Η | CHs | CHs | Cl | H | SO2 | 2 |
| 5.257 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | Cl | H | SO2 | 0 |
| 5.258 | Η | Η | Η | Η | Η | Η | CH3 | CHs | Cl | H | SO2 | 2 |
| 5.259 | CH3 | CH3 | Η | Η | Η | Η | CHs | CH3 | Cl | Cl | SO2 | 0 |
| 5.260 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CHs | Cl | Cl | SO2 | 2 |
| 5.261 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | Cl | Cl | SO2 | 0 |
| 5.262 | Η | Η | Η | CH3 | Η | Η | CH3 | CHs | Cl | Cl | SO2 | 2 |
| 5.263 | Η | Η | ch3 | CHs | Η | Η | CHs | CHs | Cl | Cl | S02 | 0 |
| 5.264 | Η | Η | CH3 | CH3 | Η | Η | CH3 | CHs | Cl | Cl | S02 | 2 |
| 5.265 | Η | Η | Η | Η | Η | Η | CHs | ch3 | CH3 | CH3 | SO2 | 0 |
| 5.266 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | CH3 | S02 | 2 |
| 5.267 | CH3 | CH3 | Η | Η | Η | Η | CH3 | ch3 | CH3 | CH3 | SO2 | 0 |
| 5.268 | CH3 | CH3 | Η | Η | Η | Η | CH3 | CH3 | CH3 | ch3 | S02 | 2 |
| 5.269 | Η | Η | Η | CHs | Η | Η | CHs | CH3 | CH3 | CH3 | SO2 | 0 |
| 5.270 | Η | Η | Η | CH3 | Η | Η | CH3 | CH3 | CH3 | ch3 | SO2 | 2 |
| 5.271 | Η | Η | CH3 | CHs | Η | Η | CH3 | CHs | CH3 | CH3 | SO2 | 0 |
| 5.272 | Η | Η | CH3 | CHs | Η | Η | CH3 | CH3 | CH3 | CH3 | S02 | 2 |
| Poř.č. | RS | RS | R7 | R® | Ri | R2 | R3 | R4 | M | L | X | n |
| 5.273 | H | H | H | H | H | CH3 | H | CH3 | H | H | 0 | 0 |
| 5.274 | H | H | H | H | H | CH3 | H | CH3 | H | H | 0 | 2 |
| 5.275 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | H | H | 0 | 0 |
| 5.276 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | H | H | 0 | 2 |
| 5.277 | H | H | H | CH3 | H | CH3 | H | CH3 | H | H | 0 | 0 |
| 5.278 | H | H | H | CH3 | H | CH3 | H | CH3 | H | H | 0 | 2 |
| 5.279 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | H | H | 0 | 0 |
| 5.280 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | H | H | 0 | 2 |
| 5.281 | H | H | H | H | H | CH3 | H | CH3 | CH3 | H | 0 | 0 |
| 5.282 | H | H | H | H | H | CH3 | H | CH3 | CH3 | H | 0 | 2 |
| 5.283 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | CH3 | H | 0 | 0 |
| 5.284 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | ch3 | H | 0 | 2 |
| 5.285 | H | H | H | CH3 | H | CH3 | H | CH3 | ch3 | H | 0 | 0 |
| 5.286 | H | H | H | CH3 | H | CH3 | H | CH3 | CH3 | H | 0 | 2 |
| 5.287 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | CH3 | H | 0 | 0 |
| 5.288 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | ch3 | H | 0 | 2 |
| 5.289 | H | H | H | H | H | CH3 | H | CH3 | Cl | H | 0 | 0 |
| 5.290 | H | H | H | H | H | CH3 | H | CH3 | Cl | H | 0 | 2 |
| 5.291 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | C 1 | H | 0 | 0 |
| 5.292 | CH3 | CH3 | H | H | H | CH3 | H | CH3 | Cl | H | 0 | 2 |
| 5.293 | H | H | H | CH3 | H | CH3 | H | CH3 | Cl | H | 0 | 0 |
| 5.294 | H | H | H | CH3 | H | CH3 | H | CH3 | Cl | H | 0 | 2 |
| 5.295 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | Cl | H | 0 | 0 |
| 5.296 | H | H | CH3 | CH3 | H | CH3 | H | CH3 | Cl | H | 0 | 2 |
| 5.297 | H | H | H | H | H | CH3 | H | CH3 | Cl | Cl | 0 | 0 |
- 57 ··· · ·· ·· · · · · • · · · ·· • · · ···· · • · · · · ·«· ··· ·· ··
| Poř . č. | RS | R6 | R7 | R8 | Rl | R2 | R3 | R4 | M | L | X | n |
| 5.298 | H | H | H | H | H | Cřfa | H | ch3 | Cl | Cl | 0 | 2 |
| 5.299 | ch3 | CH3 | H | H | H | ch3 | H | ch3 | Cl | Cl | 0 | 0 |
| 5.300 | ch3 | ch3 | H | H | H | ch3 | H | Cřfa | Cl | Cl | 0 | 2 |
| 5.301 | H | H | H | CH3 | H | ch3 | H | Cřfa | Cl | Cl | 0 | 0 |
| 5.302 | H | H | H | ch3 | H | ch3 | H | ch3 | Cl | Cl | 0 | 2 |
| 5.303 | H | H | ch3 | ch3 | H | Cřfa | H | Cřfa | Cl | Cl | 0 | 0 |
| 5.304 | H | H | ch3 | ch3 | H | ch3 | H | Cřfa | Cl | Cl | 0 | 2 |
| 5.305 | H | H | H | H | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 5.306 | H | H | H | H | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 5.307 | Cřfa | ch3 | H | H | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 5.308 | ch3 | ch3 | H | H | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 5.309 | H | H | H | CH3 | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 5.310 | H | H | H | ch3 | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 5.311 | H | H | CH3 | ch3 | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 5.312 | H | H | ch3 | ch3 | H | ch3 | H | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 5.313 | H | H | H | H | H | ch3 | H | ch3 | OCřfa | H | 0 | 0 |
| 5.314 | H | H | H | H | H | ch3 | H | ch3 | 0CH3 | H | 0 | 2 |
| 5.315 | ch3 | ch3 | H | H | H | ch3 | H | Cřfa | OCřfa | H | 0 | ’ 0 |
| 5.316 | CH3 | ch3 | H | H | H | ch3 | H | Cřfa | OCřfa | H | 0 | 2 |
| 5.317 | H | H | H | ch3 | H | ch3 | H | Cřfa | OCřfa | H | 0 | 0 |
| 5.318 | H | H | H | ch3 | H | ch3 | H | ch3 | OCřfa | H | 0 | 2 |
| 5.319 | H | H | Cřfa | ch3 | H | ch3 | H | Cřfa | OCřfa | H | 0 | 0 |
| 5.320 | H | H | ch3 | CH3 | H | ch3 | H | Cřfa | 0CH3 | H | 0 | 2 |
| 5.321 | H | H | H | H | H | CH3 | H | Cřfa | H | H | s | 0 |
| 5.322 | H | H | H | H | H | Cřfa | H | Cřfa | H | H | s | 2 |
·· • · 0 0
0 · 0 • 0 0* ·
0 · ·♦
- 58 • 0 · 0 0
0 • 0 • · •00 ·00
| Poř.č . | RS | RS | R7 | RS | Rl | R2 | R3 | R4 | M | L | X | n |
| 5.323 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | H | H | Š | 0 |
| 5.324 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | H | H | S | 2 |
| 5.325 | H | H | H | Cfc | H | Cfc | H | Cfc | H | H | S | 0 |
| 5.326 | H | H | H | Cfc | H | Cfc | H | Cfc | H | H | S | 2 |
| 5.327 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | H | H | S | 0 |
| 5.328 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | H | H | S | 2 |
| 5.329 | H | H | H | H | H | Cfc | H | Cfc | Cfc | H | S | 0 |
| 5.330 | H | H | H | H | H | Cfc | H | Cfc | Cfc | H | S | 2 |
| 5.331 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cfc | H | S | 0 |
| 5.332 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cfc | H | S | 2 |
| 5.333 | H | H | H | Cfc | H | Cfc | H | Cfc | Cfc | H | S | 0 |
| 5.334 | H | H | H | Cfc | H | Cfc | H | Cfc | Cfc | H | S | 2 |
| 5.335 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cfc | H | S | 0 |
| 5.336 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cfc | H | S | 2 |
| 5.337 | H | H | H | H | H | Cfc | H | Cfc | Cl | H | S | 0 |
| 5.338 | H | H | H | H | H | Cfc | H | Cfc | Cl | H | S | 2 |
| 5.339 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cl | H | S | 0 |
| 5.340 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cl | H | S | 2 |
| 5.341 | H | H | H | Cfc | H | Cfc | H | Cfc | Cl | H | s | 0 |
| 5.342 | H | H | H | Cfc | H | Cfc | H | Cfc | Cl | H | s | 2 |
| 5.343 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cl | H | s | 0 |
| 5.344 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cl | H | s | 2 |
| 5.345 | H | fc | H | H | H | Cfc | H | Cfc | Cl | Cl | s | 0 |
| 5.346 | H | H | H | H | H | Cfc | H | Cfc | Cl | Cl | s | 2 |
| 5.347 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cl | Cl | s | 0 |
ΦΦ· · φφ • φ φ · φ • · · · · · • · · φ φ • · φφφφ · • φφφ • · · · φφ φ φ
| Ρ ο ř . č . | R.s | RS | R7 | R8 | R1 | R2 | R3 | R4 | M | L | X | n |
| 5.348 | ch3 | CH3 | Η | Η | Η | CH3 | H | Cto | Cl | Cl | S | 2 |
| 5.349 | Η | Η | Η | Cto | Η | ch3 | H | Cto | Cl | Cl | s | 0 |
| 5.350 | Η | Η | Η | ch3 | Η | ch3 | H | Cto | Cl | Cl | s | 2 |
| 5.351 | Η | Η | ch3 | ch3 | Η | ch3 | H | Cto | Cl | Cl | s | 0 |
| 5.352 | Η | Η | Cto | ch3 | Η | CH3 | H | Cto | Cl | Cl | s | 2 |
| 5.353 | Η | Η | Η | Η | Η | c.h3 | H | Cto | Cto | Cto | s | 0 |
| 5.354 | Η | Η | Η | Η | Η | ch3 | H | Cto | Cto | Cto | s | 2 |
| 5.355 | ch3 | Cto | Η | Η | Η | Cto | H | Cto | Cto | Cto | s | 0 |
| 5.356 | ch3 | Cto | Η | Η | Η | Cto | H | Cto | Cto | Cto | s | 2 |
| 5.357 | Η | Η | Η | ch3 | Η | Cto | H | Cto | Cto | Cto | s | 0 |
| 5.358 | Η | Η | Η | ch3 | Η | Cto | H | Cto | Cto | Cto | s | 2 |
| 5.359 | Η | Η | Cto | ch3 | Η | Cto | H | Cto | Cto | Cto | s | 0 |
| 5.360 | Η | Η | ch3 | CH3 | Η | Cto | H | Cto | Cto | Cto | s | 2 |
| 5.361 | Η | Η | Η | Η | Η | Cto | H | Cto | Cto | Cto | s | 0 |
| 5.362 | Η | Η | Η | Η | Η | Cto | H | Cto | Cto | Cto | s | 2 |
| 5.363 | Cto | Cto | Η | Η | Η | Cto | H | Cto | OCto | H | s | 0 |
| 5.364 | ch3 | ch3 | Η | Η | Η | Cto | H | Cto | OCto | H | s | 2 |
| 5.365 | Η | Η | Η | ch3 | Η | Cto | H | Cto | OCto | H | s | 0 |
| 5.366 | Η | Η | Η | Cto | Η | Cto | H | Cto | OCto | H | s | 2 |
| 5.367 | Η | Η | ch3 | ch3 | Η | Cto | H | Cto | OCto | H | s | 0 |
| 5.368 | Η | Η | ch3 | ch3 | Η | Cto | H | Cto | OCto | H | s | 2 |
| 5.369 | Η | Η | Η | Η | Η | Cto | H | Cto | H | H | SO? | 0 |
| 5.370 | Η | Η | Η | Η | Η | Cto | H | Cto | H | H | SO? | 2 |
| 5.371 | ch3 | ch3 | Η | Η | Η | Cto | H | Cto | H | H | so? | 0 |
| 5.372 | ch3 | ch3 | Η | Η | Η | Cto | H | Cto | H | H | so? | 2 |
9 9 9 * 9 9 · 99 9 9
9 99 9 · 9 99 9 • 99 9 9 ···· • 9 99 9 9 9 9999 9
9··· · 9 · 9 · • 9 99 9*9 999 99 99
| Poř . č. | RS | RS | R7 | R® | R1 | R2 | R3 | R4 | M | L | X | n |
| 5.373 | H | H | H | ch3 | H | ch3 | H | CH3 | H | H | SO? | 0 |
| 5.374 | H | H | H | ch3 | H | ch3 | H | ch3 | H | H | SO? | 2 |
| 5.375 | H | H | ch3 | ch3 | H | ch3 | H | ch3 | H | H | SO? | 0 |
| 5.376 | H | H | ch3 | ch3 | H | ch3 | H | ch3 | H | H | SO? | 2 |
| 5.377 | H | H | H | H | H | CH3 | H | ch3 | ch3 | H | SO2 | 0 |
| 5.378 | H | H | H | H | H | ch3 | H | ch3 | ch3 | H | SO? | 2 |
| 5.379 | CH3 | CH3 | H | H | H | ch3 | H | ch3 | ch3 | H | SO? | 0 |
| 5.380 | CH3 | ch3 | H | H | H | ch3 | H | ch3 | ch3 | H | SO? | 2 |
| 5.381 | H | H | H | ch3 | H | ch3 | H | ch3 | ch3 | H | SO? | 0 |
| 5.382 | H | H | H | ch3 | H | ch3 | H | ch3 | ch3 | H | SO? | 2 |
| 5.383 | H | H | CHs | CH3 | H | ch3 | H | ch3 | ch3 | H | SO? | 0 |
| 5.384 | H | H | ch3 | ch3 | H | ch3 | H | ch3 | ch3 | H | SO2 | 2 |
| 5.385 | H | H | H | H | H | ch3 | H | ch3 | Cl | H | SO? | 0 |
| 5.386 | H | H | H | H | H | ch3 | H | Cífa | Cl | H | SO? | 2 |
| 5.387 | ch3 | CH3 | H | H | H | ch3 | H | ch3 | Cl | H | S02 | 0 |
| 5.388 | CH3 | ch3 | H | H | H | ch3 | H | ch3 | Cl | H | so? | 2 |
| 5.389 | H | H | H | CH3 | H | ch3 | H | ch3 | Cl | H | so? | 0 |
| 5.390 | H | H | H | ch3 | H | ch3 | H | ch3 | Cl | H | so? | 2 |
| 5.391 | H | H | CHs | ch3 | H | ch3 | H | CHts | Cl | H | so? | 0 |
| 5.392 | H | H | CH3 | ch3 | H | ch3 | H | ch3 | Cl | H | so? | 2 |
| 5.393 | H | H | H | H | H | ch3 | H | ch3 | Cl | Cl | so? | 0 |
| 5.394 | H | H | H | H | H | ch3 | H | ch3 | Cl | Cl | so? | 2 |
| 5.395 | CH3 | CH3 | H | H | H | ch3 | H | ch3 | Cl | Cl | so? | 0 |
| 5.396 | ch3 | ch3 | H | H | H | ch3 | H | ch3 | Cl | Cl | so? | 2 |
| 5.397 | H | H | H | ch3 | H | ch3 | H | ch3 | Cl | Cl | so? | 0 |
- 61 ···· ·· » · ·· ·· • · · «· ·· ···· ··· · · ···· ···· · ··«···« ···· · · · · · ·· ·· ··· ··· ·· ··
| Poř . č. | RS | RS | R7 | R8 | Ri | R2 | R3 | R4 | M | L | 1- X | n |
| 5.398 | H | H | H | Cfc | H | Cfc | H | Cfc | Cl | Cl | S02 | 0 |
| 5.399 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cl | Cl | so? | 2 |
| 5.400 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cl | Cl | SO2 | 0 |
| 5.401 | H | H | H | H | H | Cfc | H | Cfc | Cfc | Cfc | SO2 | 2 |
| 5.402 | H | H | H | H | H | Cfc | H | Cfc | Cfc | Cfc | SO2 | 0 |
| 5.403 | Cfc | Cfc | H | H | H | Cfc | H | Cfc | Cfc | Cfc | S02 | 2 |
| 5.404 | Cfc | CH | H | H | H | Cfc | H | Cfc | Cfc | Cfc | SO2 | 0 |
| 5.405 | H | H | H | Cfc | H | Cfc | H | Cfc | Cfc | Cfc | SO2 | 2 |
| 5.406 | H | H | H | Cfc | H | Cfc | H | Cfc | Cfc | Cfc | S02 | 0 |
| 5.407 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cfc | Cfc | S02 | 2 |
| 5.408 | H | H | Cfc | Cfc | H | Cfc | H | Cfc | Cfc | Cfc | SO2 | 2 |
Tabulka 6
| P 0 ř . č . | RS | RS | R7 | R8 | Rl | R4 | M | L | X | n |
| 6 . 1 | H | H | H | H | H | Cfc | H | H | 0 | 0 |
| 6.2 | H | H | H | H | H | Cfc | H | H | 0 | 2 |
| 6.3 | Cfc | Cfc | H | H | H | Cfc | H | H | 0 | 0 |
| 6.4 | Cfc | Cfc | H | H | H | Cfc | H | H | 0 | 2 |
| 6.5 | H | H | H | Cfc | H | Cfc | H | H | 0 | 0 |
| 6.6 | H | H | H | Cfc | H | Cfc | H | H | 0 | 2 |
φφφφ φφ φφ * Φφ • · ·· · φ φ · • · · φ ·· • φ φ φφφ φ φ • φ φφφ * φφ φφφ φφ φφ
| Poř.č. | R5 | R6 | R7 | R8 | Ri | R4 | Μ | L | X | η |
| 6.7 | Η | Η | CH3 | CH3 | Η | Cffe | Η | Η | 0 | 0 |
| 6.8 | Η | Η | CH3 | Cffe | Η | Cffe | Η | Η | 0 | 2 |
| 6.9 | Η | Η | Η | Η | Η | Cffe | Cffe | Η | 0 | 0 |
| 6.10 | Η | Η | Η | Η | Η | Cffe | Cffe | Η | 0 | 2 |
| 6.11 | CH3 | CH3 | Η | Η | Η | Cffe | Cffe | Η | 0 | 0 |
| 6.12 | CH3 | CH3 | Η | Η | Η | Cffe | Cffe | Η | 0 | 2 |
| 6.13 | Η | Η | Η | Cffe | Η | Cffe | Cffe | Η | 0 | 0 |
| 6.14 | Η | Η | Η | Cffe | Η | Cffe | Cffe | Η | 0 | 2 |
| 6.15 | Η | Η | CH3 | Cffe | Η | Cffe | Cffe | Η | 0 | 0 |
| 6.16 | Η | Η | CH3 | Cffe | Η | Cffe | Cffe | Η | 0 | 2 |
| 6.17 | Η | Η | Η | Η | Η | Cffe | C1 | Η | 0 | 0 |
| 6.18 | Η | Η | Η | Η | Η | Cffe | C1 | Η | 0 | 2 |
| 6.19 | CH3 | CH3 | Η | Η | Η | Cffe | C1 | Η | 0 | 0 |
| 6.20 | CH3 | CH3 | Η | Η | Η | Cffe | C1 | Η | 0 | 2 |
| 6.2 1 | Η | Η | Η | Cffe | Η | Cffe | C1 | Η | 0 | 0 |
| 6.22 | Η | Η | Η | Cffe | Η | Cffe | C1 | Η | 0 | 2 |
| 6.23 | Η | Η | CH3 | Cffe | Η | Cffe | C1 | Η | 0 | 0 |
| 6.24 | Η | Η | CH3 | Cffe | Η | Cffe | C1 | Η | 0 | 2 |
| 6.25 | Η | Η | Η | Η | Η | Cffe | C 1 | C1 | 0 | 0 |
| 6.26 | Η | Η | Η | Η | Η | Cffe | C1 | C1 | 0 | 2 |
| 6.27 | CH3 | CH3 | Η | Η | Η | Cffe | C1 | C1 | 0 | 0 |
| 6.28 | CH3 | CH3 | Η | Η | Η | Cffe | Cl | C1 | 0 | 2 |
| 6.29 | Η | Η | Η | Cffe | Η | Cffe | Cl | C1 | 0 | 0 |
| 6.30 | Η | Η | Η | Cffe | Η | Cffe | Cl | C1 | 0 | 2 |
- 63 ···· ·· ·· ·· ··· ·· ·· · · · · ··· · · · · ·· • · · · · · · ··· · 0 • 000 0 · ··· ·· ·· 000 ··· ·· ··
| P o ř . č . | RS | R6 | R7 | RQ | Ri | R4 | M | L | X | n |
| 6.31 | H | H | CH3 | CH3 | H | CH3 | Cl | C 1 | 0 | 0 |
| 6.32 | H | H | CH3 | CH3 | H | CH3 | Cl | Cl | 0 | 2 |
| 6.33 | H | H | H | H | H | ch3 | CH3 | CH3 | 0 | 0 |
| 6.34 | H | H | H | H | H | CH3 | CH3 | CH3 | 0 | 2 |
| 6.35 | CH3 | CH3 | H | H | H | CH3 | CH3 | CH3 | 0 | 0 |
| 6.36 | CH3 | CH3 | H | H | H | CH3 | CH3 | CH3 | 0 | 2 |
| 6.37 | H | H | H | CH3 | H | CH3 | CH3 | CH3 | 0 | 0 |
| 6.38 | H | H | H | CH3 | H | CH3 | CH3 | CH3 | 0 | 2 |
| 6.39 | H | H | CH3 | ch3 | H | ch3 | CH3 | CH3 | 0 | 0 |
| 6.40 | H | H | CH3 | CH3 | H | CH3 | ch3 | CH3 | 0 | 2 |
| 6.41 | H | H | H | H | H | CH3 | H | H | S | 0 |
| 6.42 | H | H | H | H | H | CH3 | H | H | S | 2 |
| 6.43 | CH3 | CH3 | H | H | H | ch3 | H | H | S | 0 |
| 6.44 | CH3 | CH3 | H | H | H | CH3 | H | H | S | 2 |
| 6.45 | H | H | H | CH3 | H | ch3 | H | H | S | 0 |
| 6.46 | H | H | H | ch3 | H | CH3 | H | H | s | 2 |
| 6.47 | H | H | ch3 | CH3 | H | ch3 | H | H | s | 0 |
| 6.48 | H | H | ch3 | CH3 | H | CH3 | H | H | s | 2 |
| 6.49 | H | H | H | H | H | ch3 | CH3 | H | s | 0 |
| 6.50 | H | H | H | H | H | CH3 | ch3 | H | s | 2 |
| 6.51 | CH3 | CH3 | H | H | H | CH3 | CH3 | H | s | 0 |
| 6.52 | CH3 | CH3 | H | H | H | CH3 | CH3 | H | s | 2 |
| 6.53 | H | H | H | CH3 | H | CH3 | CH3 | H | s | 0 |
| 6.54 | H | H | H | ch3 | H | CH3 | CH3 | H | s | 2 |
»· · ·
- 64 • · · · • · · · · • · · • · · ·
| Poř.č. | RS | R6 | R7 | R3 | Ri | R4 | M | L | X | n |
| 6.55 | H | H | CH3 | Cřfa | H | Cřfa | Cřfa | H | s | 0 |
| 6.56 | H | H | ch3 | Cřfa | H | Cřfa | Cřfa | H | s | 2 |
| 6.57 | H | H | H | H | H | Cřfa | Cl | H | s | 0 |
| 6.58 | H | H | H | H | H | Cřfa | Cl | H | s | 2 |
| 6.59 | Cřfa | Cřfa | H | H | H | Cřfa | Cl | H | s | 0 |
| 6.60 | Cřfa | CH3 | H | H | H | 'Cřfa | Cl | H | s | 2 |
| 6.61 | H | H | H | Cřfa | H | Cřfa | Cl | H | s | 0 |
| 6.62 | H | H | H | Cřfa | H | Cřfa | Cl | H | s | 2 |
| 6.63 | H | H | Cřfa | Cřfa | H | Cřfa | Cl | H | s | 0 |
| 6.64 | H | H | Cřfa | Cřfa | H | Cřfa | Cl | H | s | 2 |
| 6.65 | H | H | H | H | H | Cřfa | Cl | Cl | s | 0 |
| 6.66 | H | H' | H | H | H | Cřfa | Cl | Cl | s | 2 |
| 6.67 | CH3 | ch3 | H | H | H | Cřfa | Cl | Cl | s | 0 |
| 6.68 | CH3 | CH3 | H | H | H | Cřfa | Cl | Cl | s | 2 |
| 6.69 | H | H | H | Cřfa | H | Cřfa | Cl | Cl | s | 0 |
| 6.70 | H | H | H | Cřfa | H | Cřfa | Cl | Cl | s | 2 |
| 6.71 | H | H | Cřfa | Cřfa | H | Cřfa | Cl | Cl | s | 0 |
| 6.72 | H | H | Cřfa | Cřfa | H | Cřfa | Cl | Cl | s | 2 |
| 6.73 | H | H | H | H | H | Cřfa | C řfa | Cřfa | s | 0 |
| 6.74 | H | H | H | H | H | Cřfa | Cřfa | Cřfa | s | 2 |
| 6.75 | ch3 | CH3 | H | H | H | Cřfa | Cřfa | Cřfa | s | 0 |
| 6.76 | CH3 | CH3 | H | H | H | Cřfa | Cřfa | Cřfa | s | 2 |
| 6.77 | H | H | H | Cřfa | H | Cřfa | Cřfa | Cřfa | s | 0 |
| 6.78 | H | H | H | Cřfa | H | Cřfa | Cřfa | Cřfa | s | 2 |
• · ·· » · · fl » · · · • · · · fl • · · ·« · ·· ··
| P o ř . č . | R5 | R6 | R7 | Ra | Rl | R.4 | M | L | X | í n |
| 6.79 | H | H | Cfe | Cfe | H | Cfe | Cfe | Cfe | S | 0 |
| 6.80 | H | H | Cfe | Cfe | H | Cfe | Cfe | Cfe | S | 2 |
| 6.81 | H | H | H | H | H | Cfe | H | H | SO? | 0 |
| 6.82 | H | H | H | H | H | Cfe | H | H | SO? | 2 |
| 6.83 | Cfe | Cfe | H | H | H | Cfe | H | H | SO2 | 0 |
| 6.84 | Cfe | Cfe | H | H | H | Cfe | H | H | SO? | 2 |
| 6.85 | H | H | H | Cfe | H | Cfe | H | H | SO? | 0 |
| 6.86 | H | H | H | Cfe | H | Cfe | H | H | SO2 | 2 |
| 6.87 | H | H | Cfe | Cfe | H | Cfe | H | H | SO? | 0 |
| 6.88 | H | H | Cfe | Cfe | H | Cfe | H | H | SO? | 2 |
| 6.89 | H | H | H | H | H | Cfe | Cfe | H | SO? | 0 |
| 6.90 | H | H | H | H | H | Cfe | Cfe | H | SO? | 2 |
| 6.91 | Cfe | Cfe | H | H | H | Cfe | Cfe | H | SO2 | 0 |
| 6.92 | Cfe | Cfe | H | H | H | Cfe | Cfe | H | SO? | 2 |
| 6.93 | H | H | H | Cfe | H | Cfe | Cfe | H | SO? | 0 |
| 6.94 | H | H | H | Cfe | H | Cfe | Cfe | H | SO? | 2 |
| 6.95 | H | H | Cfe | Cfe | H | Cfe | Cfe | H | SO? | 0 |
| 6.96 | H | H | Cfe | Cfe | H | Cfe | Cfe | H | SO2 | 2 |
| 6.97 | H | H | H | H | H | Cfe | Cl | H | SO2 | 0 |
| 6.98 | H | H | H | H | H | Cfe | C 1 | H | SO2 | 2 |
| 6.99 | Cfe | Cfe | H | H | H | Cfe | C 1 | H | SO? | 0 |
| 6.100 | Cfe | Cfe | H | H | H | Cfe | C 1 | H | SO2 | 2 |
| 6.101 | H | H | H | Cfe | H | Cfe | Cl | H | SO? | 0 |
| 6.102 | H | H | H | Cfe | H | Cfe | C 1 | H | so? | 2 |
- 66 ·· · · • · · · · ···· »· ·· · · · ···· · ···· · · ··· ·· ··· ·«· ·· ··
| Poř.č. | RS | RS | R7 | R9 | R1 | R4 | Μ | L | X | η |
| 6.103 | Η | Η | CH3 | CH3 | Η | CH3 | C1 | Η | S02 | 0 |
| 6.104 | Η | Η | CH3 | CH3 | Η | CH3 | C1 | Η | S02 | 2 |
| 6.105 | Η | Η | Η | Η | Η | CH3 | C1 | C1 | S02 | 0 |
| 6.106 | Η | Η | Η | Η | Η | CH3 | C1 | C1 | S02 | 2 |
| 6.107 | Cřfe | CH3 | Η | Η | Η | CH3 | C1 | C1 | S02 | 0 |
| 6.108 | CH3 | CH3 | Η | Η | Η | CH3 | C1 | C1 | S02 | 2 |
| 6.109 | Η | Η | Η | CH3 | Η | CH3 | C1 | C1 | S02 | 0 |
| 6.110 | Η | Η | Η | CH3 | Η | CH3 | C1 | C1 | S02 | 2 |
| 6.111 | Η | Η | CH3 | CH3 | Η | CH3 | C1 | C1 | S02 | 0 |
| 6.112 | Η | Η | CH3 | CH3 | Η | CH3 | C1 | C1 | S02 | 2 |
| 6.113 | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | S02 | 0 |
| 6.114 | Η | Η | Η | Η | Η | CH3 | CH3 | CH3 | S02 | 2 |
| 6.115 | CH3 | CH3 | Η | Η | Η | CH3 | CH3 | CH3 | S02 | 0 |
| 6.116 | CH3 | CH3 | Η | Η | Η | CH3 | CH3 | CH3 | S02 | 2 |
| 6.117 | Η | Η | Η | CH3 | Η | CH3 | CH3 | CH3 | S02 | 0 |
| 6.118 | Η | Η | Η | CH3 | Η | CH3 | CH3 | CH3 | S02 | 2 |
| 6.119 | Η | Η | CH3 | CH3 | Η | CH3 | CH3 | CH3 | S02 | 0 |
| 6.120 | Η | Η | CH3 | CH3 | Η | CH3 | CH3 | CH3 | S02 | 2 |
| 6.121 | Η | Η | Η | Η | CH3 | Η | Η | Η | 0 | 0 |
| 6.122 | Η | Η | Η | Η | CH3 | Η | Η | Η | 0 | 2 |
| 6.123 | CH3 | CH3 | Η | Η | CH3 | Η | Η | Η | 0 | 0 |
| 6.124 | CH3 | CH3 | Η | Η | CH3 | Η | Η | Η | 0 | 2 |
| 6.125 | Η | Η | Η | CH3 | CH3 | Η | Η | Η | 0 | 0 |
| 6.126 | Η | Η | Η | CH3 | CH3 | Η | Η | Η | 0 | 2 |
• fl · · ·· · ··· • · fl*
I · · «
I · · · • · · · I • · 4 ·· fl»
| Poř . č. | RS | RS | R7 | R8 | Ri | R4 | M | L | X | n |
| 6.127 | H | H | CHs | CHs | C Hs | H | H | H | 0 | 0 |
| 6.128 | H | H | CH3 | CHs | CHs | H | H | H | 0 | 2 |
| 6.129 | H | H | H | H | CHs | H | CHs | H | 0 | 0 |
| 6.130 | H | H | H | H | CHs | H | CHs | H | 0 | 2 |
| 6.131 | CH3 | CHs | H | H | CHs | H | CHs | H | 0 | 0 |
| 6.132 | CHs | ch3 | H | H | CHs | H | CHs | H | 0 | 2 |
| 6.133 | H | H | H | ch3 | ch3 | H | CHs | H | 0 | 0 |
| 6.134 | H | H | H | CHs | CHs | H | CH3 | H | 0 | 2 |
| 6.135 | H | H | CH3 | ch3 | ch3 | H | CHs | H | 0 | 0 |
| 6.136 | H | H | CH3 | ch3 | CHs | H | CH3 | H | 0 | 2 |
| 6.137 | H | H | H | H | CHs | H | Cl | H | 0 | 0 |
| 6.138 | H | H | H | Η | CHs | H | Cl | H | 0 | 2 |
| 6.139 | CH3 | CHs | H | H | CHs | H | Cl | H | 0 | 0 |
| 6.140 | CHs | CHs | H | H | CHs | H | Cl | H | 0 | 2 |
| 6.141 | H | H | H | CHs | CHs | H | Cl | H | 0 | 0 |
| 6.142 | H | H | H | CHs | CHs | H | Cl | H | 0 | 2 |
| 6.143 | H | H | CH3 | CHs | CHs | H | Cl | H | 0 | 0 |
| 6.144 | H | H | CHs | CHs | CHs | H | Cl | H | 0 | 2 |
| 6.145 | H | H | H | H | CHs | H | C 1 | Cl | 0 | 0 |
| 6.146 | H | H | H | H | CHs | H | Cl | Cl | 0 | 2 |
| 6.147 | CHs | CHs | H | H | CHs | H | Cl | Cl | 0 | 0 |
| 6.148 | CHs | CHs | H | H | CHs | H | Cl | Cl | 0 | 2 |
| 6.149 | H | H | H | CHs | CHs | H | Cl | Cl | 0 | 0 |
| 6.150 | H | H | H | CHs | CHs | H ..... | Cl | Cl | 0 | 2 |
- 68 • · φ · · « φ ΦΦΦ· • · · · · · · ·· • · · φ φ · · ···· · • · φ 9 · · · · * *Φ φφ ·ΦΦ <·· ·· **
| 1 Ρ ο ř . č . | Rs | R6 | R7 | R.9 | RA | R4 | ί M | 1- L | X | 1-1 n |
| 6.15 1 | Η | Η | CHs | CHs | CHs | H | Cl | Cl | 1 0 | 0 |
| 6.152 | Η | Η | CHs | CHs | CH3 | H | C 1 | C 1 | 0 | 2 |
| 6.153 | Η | Η | Η | Η | CH3 | H | CHs | CHs | 0 | 0 |
| 6.154 | Η | Η | Η | Η | CH3 | H | CHs | CH3 | 0 | 2 |
| 6.155 | CHs | CHs | Η | Η | ch3 | H | CHs | CHs | 0 | 0 |
| 6.156 | CH3 | CHs | Η | Η | CHs’ | H | CHs | CHs | 0 | 2 |
| 6.157 | Η | Η | Η | CH3 | ch3 | H | CHs | CHs | 0 | 0 |
| 6.158 | Η | Η | Η | CHs | CHs | H | CHs | CHs | 0 | 2 |
| 6.159 | Η | Η | CHs | CHs | CH3 | H | CHs | CHs | 0 | 0 |
| 6.160 | Η | Η | CH3 | CH3 | CH3 | H | CHs | CHs | 0 | 2 |
| 6.161 | Η | Η | Η | Η | CHs | H | H | H | s | 0 |
| 6.162 | Η | Η | Η | Η | CH3 | H | H | H | s | 2 |
| 6.163 | CH3 | CH3 | Η | Η | CH3 | H | H | H | s | 0 |
| 6.164 | CHs | CH3 | Η | Η | CH3 | H | H | H | s | 2 |
| 6.165 | Η | Η | Η | CHs | CH3 | H | H | H | s | 0 |
| 6.166 | Η | Η | Η | CHs | CHs | H | H | H | s | 2 |
| 6.167 | Η | Η | CHs | CHs | CH3 | H | H | H | s | 0 |
| 6.168 | Η | Η | ch3 | CHs | ch3 | H | H | H | s | 2 |
| 6.169 | Η | Η | Η | Η | CHs | H | CHs | H | s | 0 |
| 6.170 | Η | Η | Η | Η | ch3 | H | CHs | H | s | 2 |
| 6.171 | CHs | CHs | Η | Η | CHs | H | CHs | H | s | 0 |
| 6.172 | CHs | CHs | Η | Η | CH3 | H | CHs | H | s | 2 |
| 6.173 | Η | Η | Η | CHs | CH3 | H | CH3 | H | s | 0 |
| 6.174 | Η | Η | Η | CH3 | CH3 | H | CHs | H | s | 2 |
- 69 • · · Β · · · · • · · · Β β · Β · • * Β · Β Β · · · • · * · · Β Β Β Β Β Β Β
Β · · w Β Β ΒΒ·
ΒΒ ΒΒ Β Β Β »·· BB ΒΒ
| Ρ ο ř . č . | RS | R6 | R7 | R3 | Rl | R4 | M | L | X | n |
| 6.175 | Η | Η | Cfo | Cfo | Cfo | H | Cfo | H | s | 0 |
| 6.176 | Η | Η | Cfo | Cfo | Cfo | H | Cfo | H | s | 2 |
| 6.177 | Η | Η | Η | Η | Cfo | H | Cl | H | s | 0 |
| 6.178 | Η | Η | Η | Η | Cfo | H | C 1 | H | s | 2 |
| 6.179 | Cfo | Cfo | Η | Η | Cfo | H | Cl | H | s | 0 |
| 6.180 | Cfo | Cfo | Η | Η | Cfo | H | Cl | H | s | 2 |
| 6.181 | Η | Η | Η | Cfo | Cfo | H | Cl | H | s | 0 |
| 6.182 | Η | Η | Η | Cfo | Cfo | H | Cl | H | s | 2 |
| 6.183 | Η | Η | Cfo | Cfo | Cfo | H | Cl | H | s | 0 |
| 6.184 | Η | Η | Cfo | Cfo | Cfo | H | Cl | H | s | 2 |
| 6.185 | Η | Η | Η | Η | Cfo | H | Cl | Cl | s | 0 |
| 6.186 | Η | Η | Η | Η | Cfo | H | Cl | Cl | s | 2 |
| 6.187 | Cfo | Cfo | Η | Η | Cfo | H | Cl | Cl | s | 0 |
| 6.188 | Cfo | Cfo | Η | Η | Cfo | H | Cl | Ci | s | 2 |
| 6.189 | Η | Η | Η | Cfo | Cfo | H | Cl | Cl | s | 0 |
| 6.190 | Η | Η | Η | Cfo | Cfo | H | Cl | Cl | s | 2 |
| 6.191 | Η | Η | Cfo | Cfo | Cfo | H | Cl | Cl | s | 0 |
| 6.192 | Η | Η | Cfo | Cfo | Cfo | H | Cl | Cl | s | 2 |
| 6.193 | Η | Η | Η | Η | Cfo | H | Cfo | Cfo | s | 0 |
| 6.194 | Η | Η | Η | Η | Cfo | H | Cfo | Cfo | s | 2 |
| 6.195 | Cfo | Cfo | Η | Η | Cfo | H | Cfo | Cfo | s | 0 |
| 6.196 | Cfo | Cfo | Η | Η | Cfo | H | Cfo | Cfo | s | 2 |
| 6.197 | Η | Η | Η | Cfo | Cfo | H | Cfo | Cfo | s | 0 |
| 6.198 _ | Η | Η | Η | Cfo | Cfo | H | Cfo | Cfo | s | 2 |
- 70 • · ·· · · ♦ · · · · · ···· · · · · · «φ «· · · · ··· «* <·
| 1 Poř.č. | R5 | R6 | R.7 | R.8 | R1 | R4 | Μ | L | X | η |
| 6.199 | Η | Η | CH3 | CH3 | CH3 | Η | CH3 | CH3 | S | 0 |
| 6.200 | Η | Η | CH3 | CH3 | CH3 | Η | CH3 | CH3 | S | 2 |
| 6.201 | Η | Η | Η | Η | CH3 | Η | Η | Η | S02 | 0 |
| 6.202 | Η | Η | Η | Η | CH3 | Η | Η | Η | SO2 | 2 |
| 6.203 | CH3 | CH3 | Η | Η | CH3 | Η | Η | Η | S02 | 0 |
| 6.204 | CPÍ3 | CPÍ3 | Η | Η | CH3 | Η | Η | Η | S02 | 2 |
| 6.205 | Η | Η | Η | CH3 | CH3 | Η | Η | Η | S02 | 0 |
| 6.206 | Η | Η | Η | CH3 | CH3 | Η | Η | Η | S02 | 2 |
| 6.207 | Η | Η | CPÍ3 | CH3 | CH3 | Η | Η | Η | S02 | 0 |
| 6.208 | Η | Η | CH3 | CH3 | CH3 | Η | Η | Η | S02 | 2 |
| 6.209 | Η | Η | Η | Η | CH3 | Η | CH3 | Η | S02 | 0 |
| 6.210 | Η | Η | Η | Η | CH3 | Η | CH3 | Η | S02 | 2 |
| 6.211 | CH3 | CH3 | Η | Η | CH3 | Η | CH3 | Η | S02 | 0 |
| 6.212 | CH3 | CH3 | Η | Η | CH3 | Η | CH3 | Η | S02 | 2 |
| 6.213 | Η | Η | Η | CH3 | CH3 | Η | CH3 | Η | S02 | 0 |
| 6.214 | Η | Η | Η | CH3 | CH3 | Η | CH3 | Η | S02 | 2 |
| 6.215 | Η | Η | CH3 | CH3 | CH3 | Η | CH3 | Η | SO2 | 0 |
| 6.216 | Η | Η | CH3 | CH3 | CH3 | Η | CH3 | Η | S02 | 2 |
| 6.217 | Η | Η | Η | Η | CH3 | Η | C1 | Η | S02 | 0 |
| 6.218 | Η | Η | Η | Η | CH3 | Η | C 1 | Η | S02 | 2 |
| 6.219 | CH3 | CH3 | Η | Η | CH3 | Η | C1 | Η | S02 | 0 |
| 6.220 | CH3 | CH3 | Η | Η | CH3 | Η | C 1 | Η | S02 | 2 |
| 6.221 | Η | Η | Η | CH3 | CH3 | Η | C1 | Η | S02 | 0 |
| 6.222 | Η | Η | Η | CH3 | CH3 | Η | C1 | Η | S02 ί | 2 |
- 71 • · · · > · · a
I 9 9 9
9 9 « • · <
| P o ř . č . | RS | RS | R7 | RS | R1 | R4 | M | L | X | n |
| 6.223 | H | H | Cfc | Cfc | Cfc | H | Cl | H | SO2 | 0 |
| 6.224 | H | H | Cfc | Cfc | Cfc | H | Cl | H | SO2 | 2 |
| 6.225 | H | H | H | H | Cfc | H | Cl | H | SO2 | 0 |
| 6.226 | H | H | H | H | Cfc | H | Cl | H | SO2 | 2 |
| 6.227 | Cfc | Cfc | H | H | Cfc | H | Cl | H | SO? | 0 |
| 6.228 | Cfc | Cfc | H | H | Cfc | H | Cl | H | SO2 | 2 |
| 6.229 | H | H | H | Cfc | Cfc | H | Cl | H | SO2 | 0 |
| 6.230 | H | H | H | Cfc | Cfc | H | C 1 | H | SO2 | 2 |
| 6.231 | H | H | Cfc | Cfc | Cfc | H | Cl | H | SO2 | 0 |
| 6.232 | H | H | Cfc | Cfc | Cfc | H | Cl | H | SO2 | 2 |
| 6.233 | H | H | H | H | Cfc | H | Cfc | Cfc | SO2 | 0 |
| 6.234 | H | H | H | H | Cfc | H | Cfc | Cfc | SO2 | 2 |
| 6.235 | Cfc | Cfc | H | H | Cfc | H | Cfc | Cfc | SO2 | 0 |
| 6.236 | Cfc | Cfc | H | H | Cfc | H | Cfc | Cfc | SO2 | 2 |
| 6.237 | H | H | H | Cfc | Cfc | H | Cfc | Cfc | SO2 | 0 |
| 6.238 | H | H | H | Cfc | Cfc | H | Cfc | Cfc | SO2 | 2 |
| 6.239 | H | H | Cfc | Cfc | Cfc | H | Cfc | Cfc | SO2 | 0 |
| 6.240 | H | H | Cfc | Cfc | Cfc | H | Cfc | Cfc | SO2 | 2 |
| 6.241 | H | H | H | H | Cfc | Cfc | H | H | 0 | 0 |
| 6.242 | H | H | H | H | Cfc | Cfc | H | H | 0 | 2 |
| 6.243 | Cfc | Cfc | H | H | Cfc | Cfc | H | H | 0 | 0 |
| 6.244 | Cfc | Cfc | H | H | Cfc | Cfc | H | H | Ó | 2 |
| 6.245 | H | H | H | Cfc | Cfc | Cfc | H | H | 0 | 0 |
| 6.246 | H | H | H | Cfc | Cfc | Cfc | H | H | 0 | 2 |
| 1- Poř.č. | RS | RS | 1- 1 R7 | RS | Rl | R4 | M | L | X | n |
| 6.247 | H | H | Cfc | Cfc | Cfc | Cfc | H | H | 0 | 0 |
| 6.248 | H | H | Cfc | Cfc | Cfc | Cfc | H | H | 0 | 2 |
| 6.249 | H | H | H | H | Cfc | Cfc | Cfc | H | 0 | 0 |
| 6.250 | H | H | H | H | Cfc | Cfc | Cfc | H | 0 | 2 |
| 6.251 | Cfc | Cfc | H | H | Cfc | Cfc | Cfc | H | 0 | 0 |
| 6.252 | Cfc | Cfc | H | H | Cfc | Cfc | Cfc | H | 0 | 2 |
| 6.253 | H | H | H | Cfc | Cfc | Cfc | Cfc | H | 0 | 0 |
| 6.254 | H | H | H | Cfc | Cfc | Cfc | Cfc | H | 0 | 2 |
| 6.255 | H | H | Cfc | Cfc | Cfc | Cfc | Cfc | H | 0 | 0 |
| 6.256 | H | H | Cfc | Cfc | Cfc | Cfc | Cfc | H | 0 | 2 |
| 6.257 | H | H | H | H | Cfc | Cfc | Cl | H | 0 | 0 |
| 6.258 | H | H | H | H | Cfc | Cfc | Cl | H | 0 | 2 |
| 6.259 | Cfc | Cfc | H | H | Cfc | Cfc | Cl | H | 0 | 0 |
| 6.260 | Cfc | Cfc | H | H | Cfc | Cfc | Cl | H | 0 | 2 |
| 6.261 | H | H | H | Cfc | Cfc | Cfc | Cl | H | 0 | 0 |
| 6.262 | H | H | H | Cfc | Cfc | Cfc | Cl | H | 0 | 2 |
| 6.263 | H | H | Cfc | Cfc | Cfc | Cfc | Cl | H | 0 | 0 |
| 6.264 | H | H | Cfc | Cfc | Cfc | Cfc | Cl | H | 0 | 2 |
| 6.265 | H | H | H | H | Cfc | Cfc | Cl | Cl | 0 | 0 |
| 6.266 | H | H | H | H | Cfc | Cfc | Cl | Cl | 0 | 2 |
| 6.267 | Cfc | Cfc | H | H | Cfc | Cfc | Cl | Cl | 0 | 0 |
| 6.268 | Cfc | Cfc | H | H | Cfc | Cfc | Cl | Cl | 0 | 2 |
| 6.269 | H | H | H | Cfc | Cfc | Cfc | Cl | Cl | 0 | 0 |
| 6.270 | H | H _ | H | Cfc | Cfc | Cfc | Cl | Cl | 0 | 2 |
• *
• · · ·· • A · · · · · • · · · • · · · · · ·
| Poř . č. | RS | 1- R6 | R7 | R9 | Ri | R4 | M | L | X | n |
| 6.271 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cl | Cl | 0 | 0 |
| 6.272 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cl | Cl | 0 | 2 |
| 6.273 | H | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 6.274 | H | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 6.275 | ch3 | ch3 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 6.276 | ch3 | ch3 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 6.277 | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 6.278 | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 6.279 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 0 |
| 6.280 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | Cřfa | 0 | 2 |
| 6.281 | H | H | H | H | Cřfa | Cřfa | H | H | S | 0 |
| 6.282 | H | H | H | H | Cřfa | Cřfa | H | H | S | 2 |
| 6.283 | Cřfa | CH3 | H | H | Cřfa | Cřfa | H | H | S | 0 |
| 6.284 | ch3 | Cřfa | H | H | Cřfa | CH3 | H | H | S | 2 |
| 6.285 | H | H | H | Cřfa | Cřfa | Cřfa | H | H | s | 0 |
| 6.286 | H | H | H | Cřfa | Cřfa | Cřfa | H | H | s | 2 |
| 6.287 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | H | H | s | 0 |
| 6.288 | H | H | Cřfa | Cřfa | Cřfa | Cřfa | H | H | s | 2 |
| 6.289 | H | H | H | H | Cřfa | Cřfa | Cřfa | H | s | 0 |
| 6.290 | H | H | H | H | Cřfa | Cřfa | Cřfa | H | s | 2 |
| 6.291 | CH3 | Cřfa | H | H | Cřfa | Cřfa | Cřfa | H | s | 0 |
| 6.292 | ch3 | Cřfa | H | H | Cřfa | Cřfa | Cřfa | H | s | 2 |
| 6.293 | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | H | s | 0 |
| 6.294 | H | H | H | Cřfa | Cřfa | Cřfa | Cřfa | H | s | 2 |
• · · ·
9 · · ♦ • ♦ ·
9 9 · • · · • · · * «I · · · ·· ··
| P o ř . č . | RS | RS | R7 | R0 | Ri | R4 | M | L | X | n |
| 6.295 | H | H | CH3 | ch3 | CH3 | CH3 | CH3 | H | s | 0 |
| 6.296 | H | H | CH3 | CH3 | CH3 | CH3 | CH3 | H | s | 2 |
| 6.297 | H | H | H | H | CH3 | CH3 | C 1 | H | s | 0 |
| 6.298 | H | H | H | H | CH3 | CH3 | Cl | H | s | 2 |
| 6.299 | CH3 | CH3 | H | H | CH3 | CH3 | Cl | H | s | 0 |
| 6.300 | Cřfa | CH3 | H | H | CH3 | CH3 | Cl | H | s | 2 |
| 6.301 | H | H | H | ch3 | CH3 | CH3 | Cl | H | s | 0 |
| 6.302 | H | H | H | CH3 | CH3 | CH3 | Cl | H | s | 2 |
| 6.303 | H | H | CH3 | ch3 | CH3 | CH3 | Cl | H | s | 0 |
| 6.304 | H | H | CH3 | CH3 | CH3 | CH3 | Cl | H | s | 2 |
| 6.305 | H | H | H | H | CH3 | CH3 | Cl | Cl | s | 0 |
| 6.306 | H | H | H | H | ch3 | CH3 | Cl | Cl | s | 2 |
| 6.307 | CH3 | CH3 | H | H | CH3 | CH3 | Cl | Cl | s | 0 |
| 6.308 | CH3 | ch3 | H | H | CH3 | ch3 | Cl | Cl | s | 2 |
| 6.309 | H | H | H | CH3 | CH3 | CH3 | Cl | Cl | s | 0 |
| 6.310 | H | H | H | CH3 | CH3 | CH3 | Ci | Cl | s | 2 |
| 6.311 | H | H | CH3 | ch3 | CH3 | ch3 | Cl | Cl | s | 0 |
| 6.312 | H | H | ch3 | ch3 | CH3 | ch3 | CH3 | CH3 | s | 2 |
| 6.313 | H | H | H | H | CH3 | ch3 | CH3 | CH3 | s | 0 |
| 6.314 | H | H | H | H | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 6.315 | CH3 | CH3 | H | H | CH3 | CH3 | CH3 | CH3 | s | 0 |
| 6.316 | CH3 | CH3 | H | H | CH3 | CH3 | CH3 | CH3 | s | 2 |
| 6.317 | H | H | H | ch3 | CH3 | CH3 | CH3 | ch3 | s | 0 |
| 6.318 | H | H | H | CH3 | CH3 | CH3 | CH3 | CH3 | s | 2 |
- 75 • ·
| Po ř.č. | RS | RS | R7 | R8 | Rl | R4 | M | L | X | n |
| 6.3 19 | H | H | CH3 | ch3 | CH3 | CH3 | CH3 | CH3 | S | 0 |
| 6.320 | H | H | CH3 | ch3 | ch3 | CH3 | CH3 | CH3 | S | 2 |
| 6.321 | H | H | H | H | CH3 | CH3 | H | H | SO2 | 0 |
| 6.322 | H | H | H | H | CH3 | CH3 | H | H | SO2 | 2 |
| 6.323 | CH3 | CH3 | H | H | ch3 | CH3 | H | H | SO2 | 0 |
| 6.324 | CH3 | ch3 | H | H | CH3 | CH3 | H | H | SO2 | 2 |
| 6.325 | H | H | H | CH3 | CH3 | CH3 | H | H | SO2 | 0 |
| 6.326 | H | H | H | CH3 | CH3 | CH3 | H | H | SO2 | 2 |
| 6.327 | H | H | ch3 | CH3 | ch3 | CH3 | H | H | SO2 | 0 |
| 6.328 | H | H | ch3 | ch3 | CH3 | CH3 | H | H | SO2 | 2 |
| 6.329 | H | H | H | H | CH3 | CH3 | CH3 | H | SO2 | 0 |
| 6.330 | H | H | H | H | ch3 | ch3 | CH3 | H | SO2 | 2 |
| 6.331 | CH3 | CH3 | H | H | CH3 | CH3 | CH3 | H | SO2 | 0 |
| 6.332 | ch3 | CH3 | H | H | CH3 | CH3 | CH3 | H | SO2 | 2 |
| 6.333 | H | H | H | ch3 | CH3 | CH3 | CH3 | H | SO2 | 0 |
| 6.334 | H | H | H | CH3 | CH3 | ch3 | CH3 | H | SO2 | 2 |
| 6.335 | H | H | CH3 | CH3 | CH3 | CH3 | CH3 | H | SO2 | 0 |
| 6.336 | H | H | CH3 | CH3 | CH3 | ch3 | ch3 | H | SO2 | 2 |
| 6.337 | H | H | H | H | CH3 | CH3 | Cl | H | SO2 | 0 |
| 6.338 | H | H | H | H | CH3 | CH3 | C 1 | H | SO2 | 2 |
| 6.339 | ch3 | CH3 | H | H | CH3 | CH3 | Cl | H | SO2 | 0 |
| 6.340 | CH3 | CH3 | H | H | ch3 | ch3 | Cl | H | SO2 | 2 |
| 6.341 | H | H | H | ch3 | CH3 | ch3 | Cl | H | SO2 | 0 |
| 6.342 | H | H | H | CH3 | CH3 | CH3 | Cl | H | SO2 | 2 |
- 76 ·· «
• · ·· · ··
| P o ř . č . | RS | R6 | R7 | Re | Rl | R« | M | L | X | n |
| 6.343 | H | H | CH3 | CHs | CHs | CHs | Cl | H | SO2 | 0 |
| 6.344 | H | H | CH3 | CHs | CH3 | CHs | Cl | H | SO2 | 2 |
| 6.345 | H | H | H | H | CH3 | CHs | Cl | Cl | SO2 | 0 |
| 6.346 | H | H | H | H | CHs | CHs | Cl | Cl | SO2 | 2 |
| 6.347 | CH3 | CHs | H | H | CHs | CHs | Cl | Cl | SO2 | 0 |
| 6.348 | CHs | CH3 | H | H | CH3 | CH3 | Cl | Cl | SO2 | 2 |
| 6.349 | H | H | H | CHs | CH3 | CHs | Cl | Cl | SO2 | 0 |
| 6.350 | H | H | H | CHs | CHs | CHs | Cl | Cl | SO2 | 2 |
| 6.351 | H | H | CHs | CHs | CH3 | CHs | Cl | Cl | SO2 | 0 |
| 6.352 | H | H | CHs | CH3 | CHs | CHs | Cl | Cl | SO2 | 2 |
| 6.353 | H | H | H | H | CHs | CHs | CH3 | CHs | SO2 | 0 |
| 6.354 | H | H | H | H | ch3 | CHs | CHs | CHs | SO2 | 2 |
| 6.355 | CHs | CHs | H | H | CHs | CHs | CH3 | CH3 | SO2 | 0 |
| 6.356 | CHs | CHs | H | H | CHs | CH3 | CHs | CH3 | S02 | 2 |
| 6.357 | H | H | H | CH3 | CHs | CHs | CH3 | ch3 | SO2 | 0 |
| 6.358 | H | H | H | CHs | CHs | CHs | CH3 | CH3 | SO2 | 2 |
| 6.359 | H | H | CHs | CHs | CHs | CHs | CHs | CHs | SO2 | 0 |
| 6.360 | H | H | CH3 | CHs | CHs | CHs | CHs | CH3 | SO2 | 2 |
Příklady výroby
A) Příklady výroby výchozích materiálů a meziproduktů
1. ethylester 3-(2-bromethoxy)-2-methyl benzoové kyseliny
13,6 g {0,2 mol) methylátu sodného se rozpustí ve 200 ml ethanolu. Potom se přidá 36 g (0,2 mol) ethylesteru
3-hydroxy-2-methy1benzoové kyseliny a dvě hodiny se ohřívá při refluxu. Následně se přikape 61,4 g (0,32 mol) 1,2-dibromethanu a 20 hodin se ohřívá na teplotě refluxu. Ochlazená reakční směs se koncentruje na rotačním odparníku. Zbytek se absorbuje ethylesterem kyseliny octové a třikrát se pere zředěným hydroxidem sodným. Organická fáze se suší a oddestiluje se rozpouštědlo. Upotřebitelný produkt se čistí sloupcovou chromatografii. Výtěžek: 14,6 g oleje
NMR( 270 MHZ, CDCI3, δ v hmotn. X): 7,4 (d, 1 Η), 7,2 (tr, 1H), 6,9 (d, 1H), 4,4 (tr, 2H), 4,3 (q, 2H), 3,7 (tr, 2H), 2,4 (s, 3H), 1,5 (tr, 3H)
2. ethylester kysel i ny
3-(2-methylsulfonylthioethoxy)-2-methyl benzoové g (7 mmol) ethylesteru 3-(2-bromethoxy)-2-methylbenzoové kyseliny a 1,1 g (7,3 mmol) thiomethansu1fonátu sodného se rozpustí v 10 ml ethanolu. Reakční směs se 20 hodin ohřívá na refluxu. Potom se oddestiluje rozpouštědlo a zbytek se absorbuje v methylenchloridu a pere se vodou. Organická fáze se suší sirníkem draselným a odstraní se rozpouštědlo. Upotřebitelný produkt se čistí sloupcovou chromatografii.
Výtěžek 1,1 g (50 %)
NMR(270 MHZ, 7,0 (d, 1H), 3H), 2,4 (s,
3. ethylester 8-me t hy 1-2,3-d i hydr o-be nz -1 , 4-o xa t h i i n-7-kar bo xy1 ové kyše líny
CDCI3, δ v hmotn. %) : 7,4 (d, 1 Η), 7,2 (tr, 1H),
4,5 (tr, 2H), 4,3 (q, 2H), 3,6 (tr, 2H), 3,4 (s,
3H), 1,4 (tr, 3H)
1,0 g (3,4 mmol) ethylesteru 3-(2-methy1su1fony 11hi • · · · 4 • · « ·· ·· ···· oxy)-2-methylbenzoové kyseliny se rozpustí v 5 ml nitromethanu. Přidá se 0.42 g (3,14 mmol) chloridu hlinitého. 45 minut se míchá při teplotě místnosti. Zpracování nastává přídavkem 10 ml 2N kyseliny chlorovodíkové a následnou extrakcí MTB-etherem. Vyčištěné organické fáze se perou vodou a roztokem uhličitanu draselného, suší rozpouštěd1 o.
se sirníkem draselným oddest i 1uj e se
Výtěžek: 0,7 g (93 %)
NMR(270 MHZ, CDCls, δ v hmotn. %) : 7,5 (d, 1H), 6.9 (d, 1H). 4,5 (tr, 2H), 4,3 (q, 2H), 3,2 (tr, 2H), 2,4 (s, 3H), 1,4 (tr. 3H)
4. 8-met hy1-2,3-d ihydro-benz-1,4-oxathi in-7-karboxylová kysel i na
4,0 g ethylesteru (0,0168 mol) 8-methyl-2,3-dihydrobenz-1,4-oxathiin-7-karboxylové kyseliny se společně s 1,0 g (0,0252 mol) hydroxidu sodného ohřeje ve refluxu. 2 hodiny se při oddestiluje rozpouštědlo.
ml methano1u/vody této teplotě míchá a Reflux se absorbuje na teplotu následně se vodou. Extrahuje se etherem a potom se vodnatá fáze okyselí 2N kyseliny chlorovodíkové. Získá se upotřebitelný produkt a pere se vodou. Při 40 °C se produkt suší ve vakuové sušičce.
Výtěžek: 2.9 g (82 %)
NMR(270 MHZ, d3-DMS0, δ v hmotn. %) : 12,3 (bs, 1H), 7,3 (d,
1H), 6,9 (d, 1H), 4,4 (tr, 2H), 3,2 (tr, 2H), 2,4 (s, 3H).
5. 8-methyl-2,3-dihydro-4,4-dioxo-benz-1,4-oxythiin-7-karboxy1ová kyselina • · • · • ·
·· ·
2,8 g (0,013 mol) 8-me t hy 1-2 , 3-d i hydr o-be nz -1 , 4-o xathiin-7-karboxylové kyseliny se vloží společně s wolframatem draselným na špičce nože do 30 ml kyseliny octové. Ohřejí se na 50 °C. Přikapává se 3,3 g (0,029 mmol) 30 %ního peroxidu vodíku. Reakční roztok se udržuje ještě 4 hodiny při 50 až 60 °C. Roztok se dá do studené vody. Odsaje se usazenina, pere se vodou a suší se ve vakuové sušičce při 40 °C.
Výtěžek: 2,7 g
Teplota tavení: 234 °C
Tabulka 7
(°>n
| číslo | T | Ri | R2 | R3 | R4 | X | M | L | n | fyzikální data |
| 7, 1 | OCz Hs | H | H | H | H | O | CH3 | H | 0 | 1H-NMR (270 MHz, CDCI3,v hmotn.%): 7,5(d,1H), 6,9(d, 1 Η), 4,5(q,2H), 3,2(tr,2H), 2,4 (s,3H), 1 ,4(tr, 3H) |
| 7,2 | HO | H | H | H | H | 0 | CH3 | H | 0 | 1H-NMR (270 MHz, d6-DMSO,v hmotn. %):12,3(bs,1H). 7,3(d,1H), 6,9(d, 1H), 4,4(tr,2H), 3,2(tr,2H), 2,4 ( s, 3H) |
| 7,3 | HO | H | H | H | H | 0 | ch3 | H | 2 | FP(0 C):234 |
| 7 , 4 | OCH3 | H | H | H | H | s | CH3 | H | 0 | Fp(° C) : 57 |
- 80 • Β Β Β Β
ΒΒ · · · · • · · · · • Β · · · · · • ΒΒΒ ·· Β · Β Β Β
| číslo | Τ | R1 | J- R2 | R3 | R4 | X | Μ | L | η | fyzikální data |
| 7 .. 5 | ΟΗ | Η | Η | Η | Η | S | CH3 | Η | 0 | FP(° C):179 |
| Ί . 6 | ΟΗ | Η | Η | Η | Η | S02 | CH3 | Η | 2 | 1H-NMR (250 MHz, d6-DMS0) :13,8 ( bs), 8, 1 1(d) , 7,9 8 ( d) , 4,40 (m), 2,80 (s) |
| 7 , 7 | 0C2 Hs | Η | Η | Η | Η | 0 | C1 | Η | 0 | 1H-NMR (CDC13 ) : 7,3(2xd), 4,4(q) 1H), 4,5(q,2H), 4,5(tr ) . 3,2 (tr), 1,4(tr) |
| 7,8 | ΟΗ | Η | Η | Η | Η | 0 | C1 | Η | 0 | Fp(° C) :209 |
| 7,9 | ΟΗ | Η | Η | Η | Η | 0 | C1 | Η | 2 | FP(0 C):225 |
Tabulka 8
(%
| číslo | T | Ri | R4 | X | M | L | n | fyzikální data |
| 7, 1 | OC2 Hs | H | H | 0 | CH3 | H | 0 | 1H-NMR (270 MHz, CDC13):7,44 (d), 6,85(d), 6,50(d), 5,2 5 ( d) , 4,3 2 ( q) , 2,36(s), 1,36(tr) |
| 8,2 | OH | H | H | 0 | CH3 | H | 0 | Fp (°C) : 174 |
| 8,3 | OH | H | H | 0 | CH3 | H | 2 | Fp (°C) : 205 |
| 8,4 | OC2 h5 | H | H | 0 | Cl | H | 0 | Fp (°C) : 92 |
| 8,5 | OH | H | H | 0 | Cl | H | 0 | Fp (°C) :201 |
·· ·· • · · · • · ·· ··· * · • · · ·· ··
Výroba koncových produktů . 2 —( 8-methyl -2,3-dihydro-4,4-dioxo-benz-1,4-oxathi in-7carbonyl)-1,3-cyk1ohexand i on
0.9 g (3,72 mmol) 8-methy1-2,3-dihydro-4,4-di oxo-benzin 4 -oxathi i n-7-karboxyl ové kyseliny a 0,42 g (3,72 mmol) 1,3-cyk1ohexadi onu se rozpustí v 20 m! acetonitrilu. Následně se přidá 0,81 g (3,9 mmol) dicyk1ohexy1karbodi i midu (DCC) a míchá se několik hodin až k úplné reakci. Potom se po kapkách přidá 0,75 g (7,44 mmol) triethylaminu a 0,2 ml tri methylsi 1y1kyanidu. 3 hodiny se míchá při teplotě refluxu. Ke zpracování se reakční směs nalije do 100 ml 2%ního roztoku uhličitanu sodného. Usazenina se odsaje a vodnatá fáze se pere ethylesterem kyseliny octové. Vodnatá fáze se potom okyselí 2N
| kyselinou chlorovodíkovou. | Tí m | se | vysráž í | potřebitelný produkt. | ||
| Odsaje se, pere | se vodou a | suší | ve | vakuové | sušičce. | |
| Výtěžek: 0,6 g | ||||||
| Teplota tavení: | 201 °C | |||||
| Tabulka 9 | R5 | OH | O | M | R> | |
| r6-\ | xx'- | sZ-R7 | ||||
| R7—/ | 1 | JU- R3 | ||||
| R8 | T | II | R4 | |||
| L· | (θ)η |
| č . | Rl | R2 | R3 | R4 | R5 | R6 | R7 | RS | X | M | L | n | fyzikální data |
| 9, 1 | H | H | H | H | H | H | H | H | 0 | Cfo | H | 2 | Fp (OC) : 201 |
| 9,2 | H | H | H | H | H | H | Cfo | Cfo | 0 | Cfo | H | 2 | Fp (OC) : 177 |
| 9,3 | H | H | H | H | H | H | H | H | O | Cfo | H | 0 | FP (OC) : 1 10 |
| 9,4 | H | H | H | H | H | H | Cfo | Cfo | 0 | Cfo | H | 0 | Fp(O C) : 1 1 4 |
φ · » ♦ ♦ <
» · ·« ·· · · 1
- 82 «Φ
| Č . | Ri | R.2 | R3 | R4 | R5 | R6 | R7 | R8 | X | M | L | n | f yz i ká1 ní data |
| 9 , 5 | Η | Η | Η | Η | CH3 | CHs | Η | Η | 0 | CH3 | H | 0 | FP (OC) : 78 |
| 9 , 6 | Η | Η | Η | Η | Η | Η | Η | Η | S02 | CH3 | H | 2 | Fp(° C) ; 239 |
| 9,7 | Η | Η | Η | Η | Η | Η | CH3 | Η | S02 | CHs | H | 2 | FP(° C) :207 |
| 9,8 | Η | Η | Η | Η | Η | Η | CHs | CHs | SOz | CHs | H | 2 | FP (OC) : 243 |
| 9,9 | Η | Η | Η | Η | CHs | CHs | Η | Η | SOz | CH3 | H | 2 | Fp (°C) : 147 |
| 9,10 | Η | Η | Η | Η | Η · | Η | Η | Η | S | ch3 | H | 0 | FP (»C) : 128 |
| 9,11 | Η | Η | Η | Η | Η | Η | CHs | CH3 | S | CHs | H | 0 | Fp (OC) :54 |
| 9,12 | Η | Η | Η | Η | CH3 | CH3 | Η | Η | S | CHs | H | 0 | FP(°C) :63 |
| 9,13 | Η | Η | Η | Η | Η | Η | Η | Η | 0 | Cl | H | 0 | FP (OC) : 135 |
| 9,14 | Η | Η | Η | Η | Η | Η | CH3 | CH3 | 0 | Cl | H | 0 | Fp(0C):66 |
| čís. | RS | R.s | R7 | R8 | RI | R4 | X | M | L | n | fyzikální data |
| 10,1 | H | H | H | H | H | H | 0 | ch3 | H | 0 | FP(0 C):94 |
| 10,2 | H | H | CH3 | CHs | H | H | 0 | CHs | H | 0 | 1H-NMR (270 MHz, CDCI3):17,6(bs) 6,71(m), 6,46 (d), 5,23(d), 2,65(s), 2,33 (s) , 2,03(s), 1 , 12(s) |
| 10,3 | CHs | CHs | H | H | H | H | 0 | CHs | H | 0 | 1H-NMR (270 MHz, CDC13, izomer. směs): 17,45(g), |
ΦΦΦΦ ΦΦ • Β · ·
Φ Φ Φ
Φ Φ · · • * · · « Φ Φ Φ · • · ·· • · Φ · • ΦΦΦ • ΦΦΦΦ ·
Φ Φ Φ
ΦΦ ΦΦ
| čís. | R5 | R6 | R7 | R® | Ri | R4 | X | M | L | n | fyzikální data |
| 6,78(d), 6,68 (d), 6,47(d), 5.21 (d), 2,80 (m), 1,99(s), 1,89(m), 1 , 18(s) a 1 8,0(s), 6,78 (d), 6,68(d), 6.48(d), 5,22 (d), 2,47 (m), 2.21 (s), 1,89 (m), 1,38(s) | |||||||||||
| 10,4 | H | H | H | H | H | H | 0 | Cto | H | 2 | FP(° C):245 |
| 10,5 | H | H | Cto | Cto | H | H | 0 | Cto | H | 0 | FP(°C) : 2 1 6 |
| 10,6 | Cto | Cto | H | H | H | H | O | Cto | H | 0 | FP(OC):107 |
| 10,7 | H | H | H | H | H | H | 0 | Cl | H | 0 | FP (°C) : 108 |
| 10,8 | H | H | Cto | Cto | H | H | 0 | Cl | H | 0 | Fp(° C):56 |
vzorce I a jejich hospodářsky využitelné jak jako izomerové směsi tak i v podobě Herbicidní prostředky dobře potírají růst
Sloučeniny soli jsou vhodné, čistých i zomerů, obsahují c í jako herbicidy, sloučeniny vzorce I velmi rostlin na nekulturních plochách, zejména při velkých použitých množstvích. V kulturách jako pšenice, rýže, kukuřice, sója a bavlna působí proti plevelům a školivým travám, aniž nějak poškodí kulturní rostliny. Tento efekt nastává především při malých použitých množstvích.
V návaznosti na způsoby aplikace mohou být vzorce I, případně prostředky, které je obsahují, odstranění nežádaných rostlin ještě u dalších rostlin. Do úvahy přichází následující kultury:
s1oučeni ny po už i ty k kulturních
Al 1 i um cepa, ananas comosus arachis hypogaea, asparagus ·· «· ι «· «
I · «· ··· · « • · « ·· ·· ···· *· ·· ·· officinalis, beta vulgaris spp. rapa, brassica napus
| spp. | a | 1t i ss i | ma, beta | vu | 1 agar i s | spp . |
| va r . | napus, | br ass i | c a | napus | va r | |
| va r | . s | i 1 ve s t r i s. c ame | 1 1 | i a sinensis. | ||
| i 1 1 | i no | i nens i | s, citrus | 1 | i mo η , c | i t r us |
sinensis, coffea rabica (coffea canephora, coffea liberica), cucumis sativus, cynodon dactylon, daucus carota, elaeis guineensis, fragaria vesca, glycine max, qossypiim hirsutum, (gossypium arboreum, gossypium herbaceum, gossypium hevea brasi 1 iensis, hordeum batatas, juglans regia, lens lycopersicon 1ycopersi cum, medicago sativa, phaseolus vitifolium), helianthus annuus, vulgare, humulus lupulus, ipomoea culinaris, línům usitatissimum, ma1us spp., manihot esculenta, lunatus, phaseolus vulgaris, picea abies, pinus spp., pisum sativum, prunus avium, prunus persica, pyrus communis, ribes sylestre, ricinus communis, saccharam officinarum, secale cereale, solanum tuberosum, sorghum bicolor (sorghum vulgare), theobroma cacao, trifolium pratense, triticum aestivum, triticum durum, vicía faba, vitis vinifera, zea mays.
Kromě toho v kulturách, které se mohou sloučeniny vzorce I použít také jsou tolerantní proti použití herbicidů na základě pěstování výlučně genovými postupy.
Aplikace herbicidních prostředků, případně látek může nastat různými způsoby. Jestliže jsou účinné látky pro některé kulturní rostliny méně snesitelné, tak se mohou nánašecí techniky, u kterých se herbicidní prostředky rozstřikují pomocí rozstři kovacích zařízení tak, že listy citlivých kulturních rostlin nejsou podle možnosti pokapány tím, že účinné látky pokračují na listy dole rostoucích nežádaných rostlin nebo na nezakryté plochy půdy (post-directed, lay-by).
Sloučeniny vzorce I, případně je obsahující herbicidní prostředky se mohou používat například ve formě přímo ······ · · ·· ·· ··· · · · · · · · · • · 9 · · ···· ·· · · · · · ···· · ···· · · · · · •· ·· ··· ··· ·· ·· rozstřikovaných vodnatých roztoků. prášků, suspenzí, vysokoprocentních vodnatých, olejových nebo jiných suspenzí nebo disperzí, emulzí. olejových disperzí, past, práškových prostředků, rozprašovacích prostředků nebo granulátů rozstřikováním, mlžením, rozprašováním nebo zaléváním. Formy použití závisí na účelu použití, v každém případě mají zajistit co nejjemnější rozdělení účinné látky podle vynálezu.
Jako inertní přídavné látky v podstatě přichází do úvahy:
Frakce minerálních olejů se střední až vysokou teplotou varu, jako je kerosin nebo motorová nafta, oleje z uhelného dehtu a rovněž oleje rostlinného nebo zvířecího původu, alifatické, cyklické a aromatické uhlovodíkové látky, například parafin, tetrahydronafta 1 in, alkylované naftaleny nebo jejich deriváty, alkylované benzoly nebo jejich deriváty, alkoholy jako methanol, ethanol, propanol, butanol, cyk1ohexano1, ketony jako cyklohexanon nebo silně polární rozpouštědla, například aminy jako N-methy1pyrro1 i don nebo voda.
Vodnaté formy použití se mohou zředit z emulzních koncentraci, suspenzí, past, zesíťovaných prášků nebo granulátů dispergovatě 1ných vodou přídavkem vody. K výrobě emulzí, past nebo olejo výc h disperzí se mohou substráty jako takové, nebo rozpuštěné v oleji nebo rozpouštědle, homogenizovat ve vodě pomocí zesíťovacího, adhezního. d i s pe r ga č η í ho nebo emulgačního prostředku a případně koncentrátů sestávajících z rozpouštědla nebo oleje, které jsou vhodné k ředění vodou.
Jako povrchově aktivní látky přichází do úvahy soli alkalických kovů, alkalických zemin a amonné soli sulfonových kyselin, například kyseliny 1 igninsu1fonové, kyseliny feno 1 su1fonové, kyseliny nafta 1ensu 1 fonové a kyseliny dibutylnafta 1ensu1fonové a rovněž mastných kyselin, • · • ·
- 86 alkylsulfonátů a alkylarylsulfonátů, alkylsíranů..
1aurylethersíranů a rovněž soli su1fátovaných hexadenolů, heptadekano1ů a oktadekanolů a rovněž glykoletheru mastných alkoholů, kondenzační produkty sulf onovaného naftalenu a jejich deriváty s forma 1dehydem, kondenzační produkty naftalenu, případně naftalensufonových kyselin s fenolem a forma1dehydem, po 1 yoxyethy1enokty1feno 1ether, ethoxy1 i zovaný isookty1feno1 , oktylfenol nebo nonylfenol, a 1ky1feny1 po 1yg1yko1 ether, tributylfenylpolyglykolether, alkylarylpolyetheralkoholy, isotri deky 1 a 1 koho 1 , ethy1en-oxidové kondenzáty mastných alkoholů, ethoxy1 izováný ricinový olej, po 1yoxyethylena1kylether nebo po 1yoxypropylena1kylether, po 1yg1yko1etheracetát 1 aury1 a 1 koho 1u, sorbitester, ignin-siřičitanový výluh nebo methy1ce1u1 osa.
Práškovité, rozstřikovací nebo prachovité prostředky se mohou vyrobit mícháním nebo společným mletím účinných substancí s pevným nosičem.
Granuláty, například homogenní granuláty, se mohou vyrobit vazbou účinné látky na pevné nosiče. Pevné nosiče jsou půdní minerály jako kyselina křemičitá, křemičité gely, křemičitany, mastek, kaolin, vápenec, vápno, křída, bolus, spraš, jíl, dolomit, křemelina, síran vápenatý, síran hořečnatý, oxid hořečnatý, mleté plastické hmoty, hnojivá jako síran amonný, fosforečnan amonný, dusičnan amonný, močovina a rostlinné produkty jako obilná moučka, moučka ze stromové kůry, dřeva a slupek ořechů, celulosový prášek a jiné nosiče.
Koncentrace účinných látek vzorce I v přípravku připraveném k použití se mohou v širokém rozmezí měnit. Tyto přípravky obecně obsahují 0,001 až 98 % hmotn., přednostně 0,01 až 95 % hmotn. účinné látky. Účinná látka se přitom používá v čistotě 90 % až 100 %, přednostně 95 % až 100 % (podle • · • ·
I · · 1 fr · · · • · · · 4 • · 4 • · e·
NMR-spektra).
Přípravky se sloučeninami vzorce I podle vynálezu se mohou vyrobit například následně:
hmotnostních dílů sloučeniny čísla 9.1 se rozpustí ve směsi, která sestává a 1kyi izovaného benzolu, 10 produktu 8 až 10 mol z 80 hmotnostních dílů hmotnostních dílů adičního ethylenoxi du na mo
N-moethano1amidu kyseliny olejové, 5 hmotnostních dílů vápenné soli kyseliny dodecylbenzo1su1fonové a 5 dílů adičního produktu 40 mol na 1 mol ricinového oleje. Rozlitím a jemným rozdělením roztoku v 100 000 hmotnostních dílech vody se obdrží vodnatá disperse, která obsahuje 0,02 % hmotn. účinné látky.
hmotnostní ch ethylenoxi du hmotnostních dílů sloučeniny číslo 9.1 se rozpustí ve směsi, která sestává ze 40 hmotnostních dílů cyk1 ohexanonu, 30 hmotnostních dílů isobutanolu, 20 hmotnostních dílů adičního produktu 40 mol ethylenoxidu na 1 mol ricinového oleje. Rozlitím a jemným rozdělením roztoku v 100 000 hmotnostních dílech vody se obdrží vodnatá disperze, která obsahuje 0,02 % hmotn. účinné látky.
III. 20 hmotnostních dílů účinné látky číslo 9.1 se rozpustí ve směsi, která sestává z 25 hmotnostních dílů cyk1ohexanonu minerálních olejů s hmotnostních dílů adičního ethylenoxidu na 1 mol ricinového jemným rozdělením roztoku v 100 hmotnostních dílů frakce teplotou varu 210 až 280 °C a 10 produktu 40 mol oleje. Rozlitím a
0 0 hmo t n o s t η íc h dílech vody se obdrží vodnatá disperze, která obsahuje ·· · · • » β · 4
- 88 0,02 % hmotn. účinné látky.
IV.
v.
VI .
hmotnostních dílů účinné látky č. 9.1 se dobře promíchá s 3 hmotnostními díly sodné soli diisobutylnafta 1en-su1fonové kyseliny, 17 hmotnostními díly sodné soli kyseliny 1 igninsu1fo no vé ze siřičitanového výluhu a 60 hmotnostních dílů práškovitého gelu kyseliny křemičité a mele se v kladivovém mlýnu. Jemným rozdělením směsi ve 20 000 hmotnostních dílech vody se obdrží nástřiková břečka, která obsahuje 0,1 % hmotn. účinné látky.
hmotnostní díly účinné látky č. 9.1 se promíchají s 97 hmotnostními díly jemného kaolinu. Touto cestou se obdrží rozprašovací prostředek, který obsahuje 3 % hmotn. účinné látky.
hmotn. dílů účinné látky č. 9.1 se vnitřně promíchá vapenne 8 hmotn.
soli díly s 2 hmotnostními díly dodeky1benzo1su1fonové kyseliny, po 1yg1yko1etheru mastných alkoholů, 2 hmotnostními díly sodné soli fenolmočov i noforma1dehydového kondenzátu a 68 hmotnostními minerálního oleje. Obdrží se disperze.
díly parafinického stabilní olejnatá
VI I .
hmotnostní směsi, která c yk1ohe xano nu, isooktylfenolu ricinového o koncentrát.
díl sloučeniny č. sestává ze 70 hmotnostních dí a 10 hmotnostních dí
1e j e. Obdrž í se
9.1 se rozpustí ve hmotnostních dílů lů ethoxy1 izováného íů ethoxylizováného stabilní emulzní
VIII.
hmotnostní dí1 sloučeniny č.
9.1 se rozpustí ve
0 0 0 k «0 « k ·00 · · · <
• ·· · ne smě s i, která cyklohexanonu a (ethoxylizovaný emulsní koncentrát.
sestává z 80 2 0 hmotnostní ch ricinový olej). Obdrží hmotnostních dílů dílů Emuphoru EL se stabilní ether, dipyridyly, deriváty, močoviny.
K rozšíření účinného spektra a docílení synergického efektu se mohou přimísit 2-hetaroy1cyk1 ohexaη-1,3-di ony I s početnými zástupci jiných herbicidních nebo růst regulujících skupin činných látek a společně nanášet. Například jako složka směsi přichází do úvahy 1,2,4-thiad iazo1y, 1,3,4-thi ad i a z o 1y, amidy, kyselina aminofosforečná a její deriváty, aminotriazo1y, anilidy, (het)-ary 1oxya1kanová kyselina a její deriváty, kyselina benzoová a její deriváty, benzothiad iazinony, 2-aroy1-1 ,3-cyk1ohexadi ony, hetaryl-aryl-ketony, benzylisoxazo1 idinony, meta-CF3-fenylder i váty, karbamidany, chino 1 inkarboxylová kyselina a její deriváty, chloracetatani 1 idy, deriváty cyk1ohexan-1,3-di onu, diaziny, kyselina dichlorprop i onová a její deriváty, dihydrobenzofurany, dihydrofuran-3-ony, dinitroani 1 iny, dinitrofeno 1y, difenylha1ogenkarboxy 1ové kyseliny a jejich 3-fenyluraci 1y, imidazoly, imidazoíinony,
N-feny1-3,4,5,6-tetrahydrofta 1 i midy, oxadiazoly, oxirany, fenoly, ester aryloxy- nebo heteroary1oxyfenoxyprop i onové kyseliny, fenyloctová kyselina a její deriváty, feny1propi onová kyselina a její deriváty, pyrazoly, fenylpyrazo1y, piridaziny. piridinkarboxy 1 ová kyselina a její deriváty, pyrimidy1ether, sulfonamidy, sulonylmočovíny, triaziny, triazinony, triazolinony, triazo1karboxamidy a uráčily.
Kromě toho může být užitečné sloučeniny vzorce I samé nebo v kombinaci s jinými herbicidy smíchat a aplikovat s dalšími prostředky na ochranu růstu rostlin, například s prostředky k potírání škůdců nebo fytopatogenních hub, případně bakterií. Rovněž je zájem na mísitelnosti s roztoky minerálních
solí. které se používají a stopových prvků. Mohou se olejové koncentráty.
Použitá množství ošetření, roční doby, cíle 3,0, přednostně 0,01 až 1,0 k odstranění nedostatku ve výživě také přidávat nefytotoxické oleje a účinné látky činí podle cíle pěstování a stádia růstu 0.001 až kg./ha aktivní substance.
Příklady použití
Herbicidní účinek 2-hetaroy1cyk1ohexan-1 , 3-dionů vzorce I lze prokázat skleníkovými pokusy:
Jako pěstební nádoba sloužily plastikové květináče s jílovým pískem s 3,0 % humusu jako substrátem. Semena testovaných rostliny byly vysety podle druhu odděleně.
Při předběžném ošetření byly účinné látky emulgované nebo suspendované ve vodě naneseny přímo po výsevu pomocí jemně rozdělených trysek. Nádoby byly k podpoře klíčení a růstu uměle zavlažovány a následně byly zakryty průsvitným plastikovým krytem, než rostliny vzrostou. Toto zakrytí způsobuje rovnoměrné klíčení testovaných rostlin, jestliže testované rostliny nebyly ovlivněny účinnou látkou. Množství použité pro předběžné ošetření činilo 0,0625, případně 0,0313 kg/ha aktivní substance.
Za účelem dodatečného ošetřování se testovací rostliny podle růstového typu vypěstují nejprve do výšky vzrůstu 3 až 15 cm a teprve potom se ošetřují účinnými látkami suspendovanými nebo emulgovanými ve vodě. Testovací rostliny se proto buď přímo vysejí a pěstují ve stejné nádobě, nebo se nejprve pěstují odděleně jako výsadbové rostliny a několik dní před ošetřením se vysadí do pokusné nádoby.
-91Rostliny byly udržovány specificky podle druhu při teplotách 10 až 25 °C, případně 20 až 35 °C. Zkušební perioda trvala 2 až 4 týdny. Během této doby byly rostliny ošetřovány a byla očekávána jejich reakce na jednotlivá ošetření.
Vyhodnocení bylo provedeno podle stupnice od 0 do 100. Přitom 100 znamená žádné vzejití rostlin, případně úplné zničení alespoň nadzemních částí a 0 žádné poškození nebo normální průběh vzrůstu.
Rostliny použité ve skleníkových pokusech se sestávají z následujících typů
| Latinské označení | České označení | Anglické označení |
| chenopodium album | bílý me r1í k | 1ambsquarters |
| ( CHEAL) | (gossefoot) | |
| echinochloa crus-galli | krmné proso | barnyardgrass |
| (ECHCG) | ||
| solanum nigrům | černý lilek | black nightshade |
| (SOLNÍ) | ||
| t r i t i cum aestivum | ozimá pšenice | winter wheat |
| (TRZAW) | ||
| Zea mays | kukuř i ce | Indián corn |
(ZEAMX)
Tabulka 11
Selektivní herbicidní aktivita skleníku při dodatečném použití ve 0 OH
O O
O • · · · • · • · • · ·
- 92 Příklad č. 9.1
Použité množství (kg/ha aktivní substance) 0.0625 0,0313 poškození v %
| Testované rostliny | ||
| TRZAW | 0 | 0 |
| ZEAMX | 1 5 | 0 |
| ECHCG | 90 | 90 |
| CHEAL | 95 | 95 |
| SOLNÍ | 90 | 85 |
-,Λ kancelář zfcLt“f' KALENŠKÝ a PARTNEŘI Λί z- ;?, HaiKůvg 3 KaSKg --pÍjbíiKa
Claims (7)
- NÁROKYDeriváty hetaroylu vzorce I kde mají substituenty následující význam:L, M vodík, Ci-Cs -alkyl, C? -Cé ~a 1 keny 1 , Ci-C4-a 1 koxy, přičemž tyto skupiny substituovány jedním až pěti atomy Cl-C4-a 1koxy, halogen, kyano, nitro,C2 -C6 -alkinyl , jsou případně halogenu neboX kvslík nebo síra, která je případně substituována $ jedním nebo dvěma atomy ky^íku, n nula, jedna, dvě,R1 vodík, Ci-Ce-alkyl,Ci-C4-a 1 koxy, přičemž substituovány jedním Ci-C4-a 1 koxy, halogen.C2—Ce-alkenyl, tyto skupiny až pěti atomyC2 -Ce -alkinyl , jsou případně halogenu nebo fenyl, který je případně substituován jednoduše nebo několikanásobně následujícími skupinami: Ci -C4-alkyl, vodík, Ci-C4-a 1 ko xy, ha 1ogena1koxy, halogen, k a r b o n y 1 ,R2 vodík, Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-Ce-a 1 k i ny 1 , Ci -C4-a I koxy, přičemž tyto skupiny jsou případněCi -C4 -ha 1 ogena 1 kyl , Ct -C4 · nitro, kyano, Ci -C4 -a 1 ky 1 o xy· • · · · · · ·· ··94 substituovány jedním až Ci-C4-a 1 koxy, halogen, pěti atomy halogenu nebo fenyl, který je případně substituován jednoduše nebo několikanásobně následujícími skupinami: Ci-C4-a 1ky1 ,Ci -C4 -ha 1 ogena 1 ky 1 , Ci-C4nitro, kyano, Ci-C4-a 1 ky 1 oxyvodík, Ci-C4-a 1 koxy, halogenalkoxy, halogen, karbonyl, R2 a R.3 mohou t.vořit vazbu.R3 vodík, Ci-Ce-alkyl, Ci-C4-a 1koxy, přičemž substituovány jedním Ci-C4-a 1koxy, halogen.C2 -Ce -a 1 keny 1 , tyto skupiny až pěti atomyC? —Ce -alkinyl , jsou případně ha 1 oqenu nebo fenyl, který je případně substituován jednoduše nebo několikanásobně následujícími skupinami: C1-C4-alkyl.Ci-C4-ha 1 ogena 1 ky 1 , Ci -C4 nitro, kyano, Ci-C4-a l ky 1 oxy· vodík, Ci-C4-a 1 koxy, halogenalkoxy, halogen, karbonyl, R2 a R3 mohou tvořit vazbu,R4 vodík, Ci-Ce-alkyl, Ci-C4-a 1 koxy, přičemž substituovány jedním Ci-C4-a 1koxy, halogen,C2 -C6 -alkenyl , tyto skupiny až pěti atomyC2 -Ce -alkinyl , jsou případně halogenu nebo cyk1ohexan-1,3-dion vázaný na dvou místech, vzorce II fenyl, který je případně substituován jednoduše nebo několikanásobně následujícími skupinami: Ci-C4-alkyl, vodík, Ci-C4-a 1 koxy, Ct-C4-ha 1 ogena 1 kyl , C1-C4halogenalkoxy, halogen, nitro, kyano, Ci-C4-alkyloxykarbonyl , • · • · ·· ··II ve kterém mají substituenty následující význam:R6 a R10 vodík, Ci -Ca -a 1 ky 1 ,R7 vodík, Ci-C4-alkyl, C3-C4-cyk 1 oa 1 ky 1 , přičemž tyto skupiny případně nesou jeden až tři následující substituenty: halogen, Ci—C4-thioa1ky1 neboCi-C4-a 1 ko xy, neboR7 Ci -C4 -a 1 koxy, Ci-Ce-a 1 koxya 1 ky 1 , tetrahydropyranyl-3 , tetrahydropyranyl-4, nebo r7 a R9 případně tvoří společnou vazbu nebo tří až šesti členný karbocyk1 ický prstenec, rs vodík, Ci -C4 -alkyl,R9 vodík, Ci-C4-alkyl nebo skupina COOR11,R1 1 Ci -C4 -alkyl , a rovněž hospodářsky použitelné soli.
- 2. Deriváty hetaroylu vzorce IaL • · • ·99 9 • 9- 96 ve kterém značí L vodík. Ci — Ce — alkyl, C2 — Ce alkenyl. C2 -Ce -a 1 k i ny 1 , Ci -Ca -a 1 koxy, Ci-C4-ha 1 ogena 1 kyl , Čichal ogena 1 koxy, halogen, kyano nebo nitro a M vodík. Ci —Ce -alkyl. Cz -Ce -a 1 ke ny 1 , C2 -Ce -a 1 k i ny 1 , Ci-C4-a 1 ko xy. Ci-C4 —ha 1 ogena 1 ky 1 , Ci -C4 -ha I oae na i koxy. halogen, kyano nebo nitro a O, X, R1 až R4 a n mají význam uvedený v nároku 1 .
- 3. Deriváty hetaroylu vzorce IbIb ve kterém značí L Ci — Ce-alkyl, C2 — Ce — a 1 kenyl , C2—C6alkinyl, Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 kyl . Ci-C4-ha 1 ogenalkoxy, halogen, kyano nebo nitro a M vodík, Ci-Cs-alkyl, C2 —Ce -a 1 keny 1 , C2-Ce-a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci -C4 -ha 1 ogenalkyl, Ci-C4-ha 1 ogena 1 koxy, halogen, kyano nebo nitro a O, X, R1 až R4 a n mají význam uvedený v nároku 1.
- 4. Deriváty hetaroylu vzorce I podle nároku 1, vyznačující se tím, že zbytky L a M značí vodík, methyl, methoxy, chlor, kyano, nitro a trifluormethyl.
- 5. Deriváty hetaroylu vzorce IcIc ve kterém značí L vodin. C2-Ce-a 1 k i ny 1 , Ci-C4-a 1 koxy,Ci -Ce-alkyl . C2-Ce-a 1 keny iCi -C4 -halogenalkyl. Ci -Ca ·· ·· » · · 4 » · ·· ·· · · 4 • · 4 ·· ·· ha 1ogena1koxy, halogen, kyano nebo nitro a M vodík, Cí -C6-alkyl, C2 -Ce -a l ke ny l , C2-Ce-a l k i ny l , Ci-C4-a l koxy, Ci -C4-ha l ogena I kyl , Ci -C4-ha l ogena l koxy, halogen, kyano nebo nitro a 1 .0. R1 až R4 a n mají význam uvedený v nárokuDeriváty hetaroylu vzorce IdId ve kterem C2-Ce-a I k i ny 1 , Ci-C4-a 1 koxy, ha 1ogena1koxy, halogen, kyanoC2-Ce-alkenyl, Ci-C4-ha 1 ogena 1 ky 1 , Ci-C4 nebo nitro a M vodík,Ci-Ce-alkyl, C2-Ce-a 1 keny 1 , C2-Ce-a 1 k i ny 1 , Ci -C4 -a 1 koxy,Ci-C4-halogenalkyl nebo nitro a 0, R1Ci-C4-ha 1ogena1koxy, halogen, kyano R4 a n mají význam uvedený v nároku 1.Deriváty hetaroylu vzorce IdId ve kterém značí L vodík,“ Ci-Ce-alkyl, C2 -C6 -a 1 keny 1 ,C2-Ce-a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci -C4 -ha 1 oge na 1 ky 1 , Ci -C4 halogen, kyano nebo nitro a M vodík, C? -Ce -a 1 keny 1 , C2-Ce-a 1 k i ny 1 , Ci -C4 -a 1 koxy,Ci-C4-ha 1 ogena 1 ky 1 , Ci-C4-ha 1 ogena 1 koxy, halogen, kyano nebo nitro, m značí O, 1 nebo 2 a 0, R1 , R4 a n mají význam uvedený v nároku 1.ha 1ogena1koxy, Ci -Ce -alkyl ,Deriváty hetaroylu vzorce 1'e ·· ·· • · · · · · • · · ·· · · · • · · · · ··· ··· · · · · ve kterém značí L vodík, Ci-Cé-alkyl, C2 -Ce> -a 1 ke ny 1 , C2 -Cs -a 1 k i ny 1 , Ci -C4-a 1 koxy, Ci-C4-ha 1ogena 1ky 1 , C1-C4ha1ogena1koxy, halogen, kyano nebo nitro a M vodík, Ci -Cě -alkyl, C2 -C6 -a 1 ke nyl , C2 -Ce -a 1 k i ny 1 , Ci-C4-a 1 koxy, Ci-C4-ha 1 ogena 1 ky 1 , Ci-C4-ha 1 o ge na 1 ko xy, halogen, kyano nebo nitro, m značí O, 1 nebo 2 a Q, R1 až R4 a n mají význam uvedený v nároku 1.Způsob výroby sloučeniny vzorce I vyznačující se tím, že se výchozí látka podle nároku vzorce IIOHII vzorce lila nebo kyselinou vzorce acylizuje acylchloridemaž R4 mají význam uvedený v nároku 1, acvlizace za přítomnosti katalyzátoruM. X, R.1 produkt přičemž L načež se podrobí přesmyku na sloučeninu vzorce I
- 10. Deriváty hetaroylu vzorce II Ic • · 4 k · · <·· ··Dle kde T, L, Μ, X, R1 až R4 a n mají následující význam;chlor, OH nebo Ci~C4~alkoxy vodík, Ci-Cg-alkyl, Ci-C4-a 1 ko xy, přičemž subst i tuoványC2 -Cg -alkenyl , tyto skupiny až pěti atomy jedni mCi -C4-a 1koxy, halogen, kyano, nitro,C2 -Cg -alkenyl , tyto skupiny až pěti atomy vodík, Ci-Cg -alkyl, Ci —C4 -a 1 ko xy, přičemž subst i tuovány jedni mCi -C4-a 1koxy, halogen, kyano, nitro,X, R1 až R4 a n mají význam jako v nároku 1.
- 11. Deriváty hetaroylu vzorce Illd ·· ·· » · · 4 k · · · ··· · 4 • · ·· ··C2 -Cg -alkinyl, jsou případně halogenu neboC2 ~Cg -alkinyl, jsou případně halogenu nebo ma kde T, L, Μ, X, R1 až R4 a n mají následující význam;chlor, OH nebo Ci -C4-a 1 ko xy » · · flI · ··99 4 9 fl • · fl ·· ··- 100 ···· flflL Ci-Ce-alkyl. C2-Ce-a 1 keny 1 . C2-Ce ~a 1 k i ny 1 , alkoxy, přičemž tyto skupiny jsouCi —Ca — pří pádně
subst i tuovány Ci -C4 -a 1 koxy, jedni m halogen. až pěti a t omy kyano, nitro. halogenu nebo M vodík , Ci -Ce -alkyl. C2 -Ce -alkenyl, C2 -Ce -alkinyl. Ci -C4 -a lkoxy. přičemž tyto skupí ny jsou případně subst i tuovány jedni m až pěti a torny halogenu nebo Ci -C4 -alkoxy. halogen, kyano, nitro, X, RA až R4 a n maj í význam jako v nároku 1. 12. Použití derivátu hetaroylu vzorce I podl e nároku 1 a přídavné látky jako herbicidního prostředku. 13. Použití derivátu hetaroylu vzorce I podl e nároku 1 v herbicidně účinném množství k potírání nežádoucího růstu rostlin působením na rostliny nebo jejich životní prostředí.
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| DE19607105A DE19607105A1 (de) | 1996-02-24 | 1996-02-24 | 2-Hetaroylcyclohexan-1,3-dione |
| DE1996112687 DE19612687A1 (de) | 1996-03-29 | 1996-03-29 | 2-Hetaroylcyclohexan-1,3-dione |
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| CZ982681A CZ268198A3 (cs) | 1996-02-24 | 1997-02-20 | 2-hetaroylcyklohexan- 1,3-diony, způsob jejich výroby a jejich použití |
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| US (1) | US6013607A (cs) |
| EP (1) | EP0888334B1 (cs) |
| JP (1) | JP2000505449A (cs) |
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| CN (1) | CN1096458C (cs) |
| AR (1) | AR005956A1 (cs) |
| AT (1) | ATE221526T1 (cs) |
| AU (1) | AU728500B2 (cs) |
| BG (1) | BG64005B1 (cs) |
| BR (1) | BR9707721A (cs) |
| CA (1) | CA2247167C (cs) |
| CZ (1) | CZ268198A3 (cs) |
| DE (1) | DE59707863D1 (cs) |
| EA (1) | EA001930B1 (cs) |
| IL (1) | IL125550A (cs) |
| NZ (1) | NZ331123A (cs) |
| PL (1) | PL328505A1 (cs) |
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| KR20010052277A (ko) | 1998-04-30 | 2001-06-25 | 스타르크, 카르크 | 시클로헥센온디옥소티오크로마노일 유도체 |
| CA2355125A1 (en) * | 1998-12-15 | 2000-06-22 | Basf Aktiengesellschaft | Thiochromanoylcyclohexenone derivatives |
| AR023255A1 (es) * | 1999-05-13 | 2002-09-04 | Idemitsu Kosan Co | Compuestos azoles y composiciones herbicidas que los contienen |
| WO2001074802A1 (fr) * | 2000-04-04 | 2001-10-11 | Idemitsu Kosan Co., Ltd. | Derives de benzoyle fondu et compositions herbicides les contenant |
| AU2002221269A1 (en) * | 2000-10-19 | 2002-04-29 | Merck & Co., Inc. | Estrogen receptor modulators |
| US6750213B2 (en) | 2000-10-19 | 2004-06-15 | Merck & Co., Inc. | Estrogen receptor modulators |
| JP4554219B2 (ja) | 2002-04-24 | 2010-09-29 | メルク・シャープ・エンド・ドーム・コーポレイション | エストロゲン受容体調節剤 |
| US8575068B2 (en) | 2010-03-23 | 2013-11-05 | Basf Se | Pyrazinothiazines having herbicidal action |
| AR081526A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridazinas sustituidas que tienen accion herbicida |
| BR112012023935A2 (pt) | 2010-03-23 | 2015-09-15 | Basf Se | piridazina substituída da fórmula i, composto para fórmula i, composição e método para o controle de vegetação indesejada |
| US8809535B2 (en) | 2010-03-23 | 2014-08-19 | Basf Se | Substituted pyridines having herbicidal action |
| EA201201322A1 (ru) | 2010-03-23 | 2013-05-30 | Басф Се | Пиридотиазины, обладающие гербицидным действием |
| CN102812024B (zh) | 2010-03-23 | 2015-01-21 | 巴斯夫欧洲公司 | 具有除草作用的取代吡啶 |
| CN103313991B (zh) | 2010-12-23 | 2016-02-10 | 巴斯夫欧洲公司 | 具有除草活性的取代吡啶 |
| US20140094368A1 (en) | 2011-06-09 | 2014-04-03 | Basf Se | Substituted Pyridines Having Herbicidal Activity |
| WO2012168241A1 (en) | 2011-06-09 | 2012-12-13 | Basf Se | Substituted pyrazines having herbicidal activity |
| EP2780339A1 (en) | 2011-11-16 | 2014-09-24 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides ii |
| BR112014026823A2 (pt) | 2012-04-27 | 2017-06-27 | Basf Se | compostos de n-(tetrazol-5-il) e n-(triazol-5-il)arilcarboxamida substituída e seu uso como herbicidas. |
| IN2014MN02343A (cs) | 2012-06-01 | 2015-08-14 | Basf Se | |
| JP2014105156A (ja) * | 2012-11-22 | 2014-06-09 | Sumitomo Seika Chem Co Ltd | 環状ジスルホン化合物の製造方法 |
| WO2014184019A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | N-(1,2,5-oxadiazol-3-yl)carboxamide compounds and their use as herbicides |
| US20160102103A1 (en) | 2013-05-24 | 2016-04-14 | Basf Se | Substituted pyridine compounds having herbicidal activity |
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| US4249937A (en) * | 1977-05-23 | 1981-02-10 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| IL77349A (en) * | 1984-12-20 | 1990-07-12 | Stauffer Chemical Co | 2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| EP0243313B1 (de) * | 1986-04-24 | 1990-05-16 | Ciba-Geigy Ag | Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung |
| CA1340284C (en) * | 1987-03-19 | 1998-12-22 | Zeneca Inc. | Herbicidal substituted cyclic diones |
| JPH04247052A (ja) * | 1991-01-31 | 1992-09-03 | Nippon Soda Co Ltd | ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法 |
| JP3245421B2 (ja) * | 1992-08-18 | 2002-01-15 | 出光興産株式会社 | シクロヘキサンジオン誘導体 |
| AU5118693A (en) * | 1992-10-15 | 1994-05-09 | Idemitsu Kosan Co. Ltd | Cyclohexanedione derivative |
| JPH08245618A (ja) * | 1995-03-08 | 1996-09-24 | Nippon Soda Co Ltd | 置換ビシクロヘプタンジオン誘導体および除草剤 |
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| Publication number | Publication date |
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| EA199800759A1 (ru) | 1999-04-29 |
| BG64005B1 (bg) | 2003-09-30 |
| ATE221526T1 (de) | 2002-08-15 |
| EA001930B1 (ru) | 2001-10-22 |
| CN1096458C (zh) | 2002-12-18 |
| SK103498A3 (en) | 1999-03-12 |
| EP0888334A1 (de) | 1999-01-07 |
| CN1211979A (zh) | 1999-03-24 |
| EP0888334B1 (de) | 2002-07-31 |
| SK282671B6 (sk) | 2002-11-06 |
| IL125550A0 (en) | 1999-03-12 |
| AU2091897A (en) | 1997-09-10 |
| KR19990087187A (ko) | 1999-12-15 |
| IL125550A (en) | 2001-11-25 |
| BR9707721A (pt) | 2005-06-07 |
| WO1997030986A1 (de) | 1997-08-28 |
| CA2247167A1 (en) | 1997-08-28 |
| US6013607A (en) | 2000-01-11 |
| CA2247167C (en) | 2005-07-12 |
| NZ331123A (en) | 2000-03-27 |
| DE59707863D1 (de) | 2002-09-26 |
| PL328505A1 (en) | 1999-02-01 |
| JP2000505449A (ja) | 2000-05-09 |
| AU728500B2 (en) | 2001-01-11 |
| AR005956A1 (es) | 1999-07-21 |
| BG102701A (en) | 1999-04-30 |
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