CA2199422A1 - Alkyl phenylacetates - Google Patents
Alkyl phenylacetatesInfo
- Publication number
- CA2199422A1 CA2199422A1 CA002199422A CA2199422A CA2199422A1 CA 2199422 A1 CA2199422 A1 CA 2199422A1 CA 002199422 A CA002199422 A CA 002199422A CA 2199422 A CA2199422 A CA 2199422A CA 2199422 A1 CA2199422 A1 CA 2199422A1
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- bond
- radical
- riii
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 Alkyl phenylacetates Chemical class 0.000 title claims abstract description 828
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 222
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 68
- 150000002367 halogens Chemical group 0.000 claims abstract description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 11
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 1088
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 852
- 150000003254 radicals Chemical class 0.000 claims description 633
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 330
- 229910052760 oxygen Inorganic materials 0.000 claims description 156
- 239000001301 oxygen Substances 0.000 claims description 154
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 153
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 133
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 87
- 229910052717 sulfur Inorganic materials 0.000 claims description 71
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 69
- 239000011593 sulfur Substances 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 7
- 229940049953 phenylacetate Drugs 0.000 claims 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 118
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000004450 alkenylene group Chemical group 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005702 oxyalkylene group Chemical group 0.000 abstract description 2
- 150000001350 alkyl halides Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000006236 oxyalkylenoxy group Chemical group 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 392
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 159
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 123
- 125000001309 chloro group Chemical group Cl* 0.000 description 97
- 239000000460 chlorine Substances 0.000 description 74
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 66
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 62
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 62
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 60
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 59
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 33
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 150000002431 hydrogen Chemical class 0.000 description 27
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 20
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000000335 thiazolyl group Chemical group 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 125000001715 oxadiazolyl group Chemical group 0.000 description 17
- 125000003226 pyrazolyl group Chemical group 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 239000010949 copper Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 14
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 14
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 13
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 13
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 13
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 13
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 13
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- 239000012442 inert solvent Substances 0.000 description 12
- 125000001786 isothiazolyl group Chemical group 0.000 description 12
- 125000000842 isoxazolyl group Chemical group 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 150000002825 nitriles Chemical class 0.000 description 12
- 125000002971 oxazolyl group Chemical group 0.000 description 12
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 12
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 11
- FMFSVZQZWVMVKB-UHFFFAOYSA-N [C]1=CN=CC=N1 Chemical class [C]1=CN=CC=N1 FMFSVZQZWVMVKB-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 125000001113 thiadiazolyl group Chemical group 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 150000005826 halohydrocarbons Chemical class 0.000 description 10
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 125000004104 aryloxy group Chemical group 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 6
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 5
- 229910052987 metal hydride Inorganic materials 0.000 description 5
- 150000004681 metal hydrides Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 4
- 125000005133 alkynyloxy group Chemical group 0.000 description 4
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 3
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 3
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 3
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 3
- 229910001948 sodium oxide Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- MEHWOCVPNCEIJO-UHFFFAOYSA-N 3-methyl-2,2-di(propan-2-yl)butan-1-amine Chemical compound CC(C)C(CN)(C(C)C)C(C)C MEHWOCVPNCEIJO-UHFFFAOYSA-N 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004995 haloalkylthio group Chemical group 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 125000004468 heterocyclylthio group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 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 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
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- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
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- 125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
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- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
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- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention pertains to phenylacetic acid alkyl esters of formula I, wherein the index and substituents are as follows: R' is formyl, alkyl carbonyl or alkyl; R'' is alkyl; U is -O-, -S-, -NH- or -NHO-; V is -O-, -S-, or -NH-; X is cyano, nitro, halogen, alkyl, alkyl halide, alkoxy, alkoxy halide, alkyl thio or, if n is > 1, optionally substituted alkylene, alkenylene, oxyalkylene, oxyalkylenoxy, oxyalkenylene, oxyalkenylenoxy or butadiendiyl; n is 0, 1, 2 or 3; R is halogen, hydroxy, mercapto, amino, carboxyl, carbonylamino or an organic radical which is bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group, or, together with an X group and the phenyl ring to which they are bonded, an optionally substituted, bicyclic, partially or completely unsaturated system. The invention also pertains to methods and intermediate products for their preparation and to their use.
Description
.
21~9~2 Alkyl phenylacetates The present invention relates to alkyl phenylacetates of the 5 formula I
Xn ~ CH(UR')-COVR'' (I) R
where 15 R' is formyl, Cl-C4-alkylcarbonyl or Cl-C4-alkyl;
R" is C1-C4-alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
~ is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or where n is ~ 1, a C3-Cj-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon ~ , ~ atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, Cl-C4-alkyl, Cl-C4-haloaLkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > l; ~
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or an organic radical which is bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino grou~
or, ~ 2 2199~22 together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
Processes and intermediates for their preparation and their use.
10 Alkyl phenylacetates are disclosed in the literature as drugs or inte -~;ate~ for their preparation lEP-A 486 011, EP-A 462 531, JP - A 03/~84,665, FR-A ~ 572 076, EP - A 166 650, JP-A S9/164,766, JP - A 56/005,439, DE - A 29 31 735, DE - A 24 49 990, JP-A 49/108,039, US - A 3,607,941, GB - A 1 230 347, DE - A 12 77 127, EP - A 065 874, 15 NL - A 75/13,439, NL - A 73/09,425, BE - A 77/06,316, FR-A 2 054 532, , EP-A 565 965, WO-A 91/17,987 and US-A 4,752,616]. In addition, EP-A 206 772 describes such compounds having herbicidal properties and US-A 3,544,304 describes similar com~ounds having growth-regulating properties.
It is an object of the present invention to provide novel compounds having fungicidal properties.
We have found that this object is achieved by the compounds I
25 defined at the outset. We have also found processes and intermediates for their preparation and their use for controlling ~n; ~1 pests or harmful fungi.
The comp~unds I are prepared by methods similar to various 30 methods known per se from the literature. In the preparation, it is not important whether the group R or the group -CH~UR')-COVR"
is synthesized first.
These groups are particularly advantageously obtained by the 35 processes described below.
A synthesis of the group -CH(UR')-COVR":
The compounds I in which U and V are each oxygen are obtained, 40 for example, by converting a benzaldehyde of the formula II with a cyanide in the manner known per se into the corresponding cyanohydrin of the formula III, hydrolyzing III in the presence of an acid with an alcohol of the formula IV to give the corresponding alkyl ~-hydroxyphenylacetate of the formula V and 45 etherifying V with a derivative of the formula VIa to give I.
~" CHO CH(OH)-CN
Xn ~ + HCN ~ Xn ~ R
II III
~ CH ( OH )--C02R ' ' 10rH+l/R''OH Xn ~ R
IV V
~ " CH(OR')-C02R'' R'-Ll~ Xn ~
R
( VIa In the formula VIa, Ll is a nucleophilically substitutable leaving 20 group, such as halogen teg. chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate)~
25 The cyanohydrin III is prepared in a manner known per se ~cf.
organikum, 15th edition (1977), page 557 et seq.; Houben-Weyl vol. VIII, 274 et se~. (1952)], usually at from O to 40 C, preferably from O to 20 C, without a solvent, in water or in an inert solvent, if necessary with phase transfer catalysis.
- Suitable HCN sources are hydrocyanic acid itself and cyanides, from which HCN is formed by the addition of a mineral acid.
Particularly suitable cyanides are ~l k~l; metal cyanides (eg.
35 potassium cyanide or sodium cyanide)O
The cyanides or HCN are used in general in equimolar amounts. It may be advantageous for the yield to use an excess of from 10 to 20 mol%, based on benzaldehyde II.
Suitable solvents are water, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, suc as methylene chloride, chloroform and 45 chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, 2199i~2~
n-butanol and tert-butanol, particularly preferably water and/or alcohols. Mixtures of the stated solvents may also be used.
When cyanides are used, the reaction is usually carried out by 5 gradually adding equimolar amounts of a mineral acid (for ~x~mple a hydrohalic acid, such as hydrochloric acid or hydrobromic acid, sulfuric or phosphoric acid). Instead of the mineral acids, equimolar amounts of acidic salts (es. ammonium chloride or ammonium sulfate) are also used. The acids or acidic salts are 10 generally used in equimolar amounts, based on cyanide.
For example, alkali metal cyanides, alkali metal carbonates, ammonia or organic bases, such as alkylamines and alcoholates, are used as basic catalysts.
i The benzaldehydes II required for the preparation of the compounds I are known in the literature (EP-A 400 417) or can be prepared according to the cited literature.
20 The hydrolysis of the cyanohydrins III to give the corresponding alkyl a-hydroxyphenylacetates of the formula V is carried out in a manner known per se [Org. Synth. Col. Vol. I (1941) 336;
US-A 2,892,847; EP-A 400 417], usually at from O to 100 C, preferably from 10 to 50 C, in the presence of an acid and R"OH as 25 a solvent. If required, an inert solvent may additionally be used. In order to liberate the cG~ ounds V from the iminoesters formed as intermediates, it is necessary to add water.
Suitable inert solvents are aliphatic hydrocarbons, such as 30 pentane, hexane, cyclohexane and petroleum ether, aromatic _ hydrocarbons, such as toluene, o-, m- and p-xylene, ( halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, 35 ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide. Mixtures of the stated solvents may also be used.
40 The acids and acidic catalysts used are inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sul~uric acid and perchloric acid, in particular hydrochloric acid and sulfuric acid. The acids are generally used in equimolar amounts.
With regard to the yield, it may be advantageous to add an excess 45 of acid.
005~/452~4 2199~22 The alkyl a-hydroxyacetates thus obtained are then etheri~ied with a derivative of the formula VIa in a manner known per se tJ-Chem. Soc. (1899), 753; Austr. J. Chem. 43 (1990), 2045; J. Org.
Chem. 47 (1982), 5404] in the presence of a base to give the 5 compounds I.
This reaction is usually carried out at from O to 80 C, preferably from O to 30-C, in an inert ~olvent.
10 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 15 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, particularly preferably tetrahydrofuran and dimethylformamide. Mixtures of the stated 20 solvents may also be used.
Suitable bases are in general inorganic ~vmpounds, such as Alk~i metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and 25 calcium hydroxide, alkali metal oxides and alkAl~nP earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, ?1 k~l; metal hydrides and ~1 kAl ~ ne earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, ~lk~l i metal amides, such as lithium 30 amide, sodium amide and potassium amide, ~lkal; metal carbonates and alk~li n~ earth metal carbonates, such as lithium carbonate and calcium carbonate, and alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and 35 phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and Al k~l ~ metal alcoholates and Al k~l;ne earth metal alcoholates, such as sodium methylate, sodium ethylate, potassium ethylate, potassium tert-butylate and dimethoxymagnesium, as well as inorganic bases, for ~F~mrle tertiary amines, such as 40 trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines. Sodium hydride is particularly preferred. The bases are used in general in equimolar amounts. However, they may also be 45 used in excess or, if required, as solvents.
:
0050/452~4 2199~22 In a modification of the process described above, the c~ Gunds of the formula I are obtained starting from the alkyl a-hydroxyphenylacetates of the formula V also by first converting the compounds V with a halogenating agent in a manner known per 5 se into the corresponding alkyl ~-halophenylacetate and then etherifying VII in the presence of a base with an alcohol of the formula VIb to give I.
Xn ~ C~OH)-C02R" tHal] X~ ~ C~(Hal)-C02R'' V VII
f ~" CH(OR')--C02R'' R'-OH~ Xn ~ R
VIb In the formula VII, Hal is halogen, in particular chlorine, bromine or iodine.
25 The halogenation of the cor~.~ounds V is carried out in a manner known per se tcf. Chem. Ber. 120 (1987), 1825], usually at from O
to 60-C, preferably from 10 to 30 C.
Suitable halogenating agents are phosphoryl bromide, phosphoryl 30 chloride, thionyl chloride, tetrab~l --thane/triphenylphosphine, boron tribromide and hydrogen bromide. An excess of the halogenating agents is generally used. The reaction i8 carried out in general in an inert solvent.
35 Suitable inert solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ethe~, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, ch~oroform and chlorobenzene, ethers, such as diethyl ether, diiso~rGpyl ether, 40 tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide 45 and dimethylformamide, and inert organic amines, such as ~050/45~4 2199~22 triethylamine and pyridine, particularly preferably toluene and acetonitrile. Mixtures of the stated solvents may also be used.
Alternatively, the aldehydes of the formula II may also be 5 converted by base-catalyzed condensation with a haloform (eg.
chloroform or bromoform) and with an alcohol of the formula R'OH
in a manner known per se tcf. J. Am. Chem. Soc. 82 (1960), 406Z]
into the corresponding a-alkoxyphenylacetic acids, from which the esters of the formula I (U = V = O) are obtainable by known 10 methods, either directly or via activated carboxylic acid derivatives.
CHO R'OH/Base 15 Xn ~ + CHHal3 20 ~ CH(OR')-~O2H
Xn ~ ~ OH(OR')-CO2R"
R R"OH ~ Xn ~ R
I (U = V = o) In a further process, the c~..~ounds I are obtained starting from alkyl a-ketophenylacetates of the formula VIII by reduction to the corresponding alkyl a-hydroxyphenylacetates of the formula V
and subsequent conversion of V into I by the processes described 30 above.
Xn ~ C(=0)--CO2R'' [H~ Xn ~ CH(OH)--C02R'' VIII V
The reduction of the alkyl a-ketophenylacetates'VIII i8 carried out in a manner known per se ~J. Chem. Soc. (1954), 520; Chem.
40 ~er. 76 (1943), 308; Chem. Ber. l~Q (1987), 1825], usually at from -100 to 100 C, preferably from 0 to 30 C, in an inert solvent.
~Amrles of suitable reducing agents are hydrides (eg. sodium 45 borohydride) and hydrogen.
2199~22 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as 5 diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, organic acids, such as acetic acid, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide 10 and dimethylformamide, particularly preferably methanol and tetrahydrofuran. Mixtures of the stated solvents may also be used.
The reduction with hydrogen is usually carried out in the 15 presence of a catalyst, such as nickel, Raney nickel, palladium ( or palladium on a carrier such as carbon.
The alkyl ~-ketocarboxylates of the formula VII which are required for this preparation process are known in the literature 20 (EP-A 206 606, EP-A 226 ~17, EP-A 242 081, EP-A 253 213, EP-A 256 667, EP-A 267 734, EP-A 278 595, EP-A 307 101, EP-A 307 103, EP-A 310 954, EP-A 335 519, EP-A 341 845, EP-A 350 691, EP-A 354 571, EP-A 363 818, EP-A 370 629, EP-A 373 775, EP-A 378 755, EP-A 382 375, EP-A 386 561, 25 EP-A 393 861, EP-A 407 873, EP-A 414 153, EP-A 426 460, EP-A 459 285, EP-A 460 575, EP-A 468 684, EP-A 472 224, EP-A 472 300, EP-A 474 042, EP-A 475 158, EP-A 480 795, EP-A 499 823, EP-A 528 245, EP-A 538 097, EP-A 564 928, EP-A 579 124, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830, 30 Wo-A 92/19,487, WO-A 92/18,494, WO-A 93/16,986, WO-A 94/11,334, JP-A 05/201,946, German Application No. P 43 05 502.8, German Application No. P 44 21 180.5, German Application No.
P 44 21 181.3 and German Application No. P 44 21 182.1) or can be prepared according to the literature cited.
The compounds of the formula I in which U is amino and V is oxygen are prepared, for example, by reacting a compound of the formula VII with a primary amine or a corresponding ammonium salt of the formula VIc in a manner known per se (~S-A 4,723,031).
0050l4S~U~
-- 9 21~9~22 ~ " CH(Hal)-CO2R" + H2NR' or salt Xn ~ R
VII VIc CH(NHR')-CO2R"
; Xn ~ R
I (U=NH, V=O) The compounds I in which U is aminooxy and V is oxygen are 15 obtained in a S; m~ 1 ~r manner by reacting VII with O-alkylhy~G~ylamines or with the corresponding hydroxylammonium salts VId.
Xn ~ CH(H~ CO2R" + H2NOR' or salt VII VId CH(NHOR')-C02R"
Xn~
R
I (U=NH-O-, V=o) ~ ' ' ~ .
Compounds I in which V is amino are obtained, for example, starting from the corresponding esters, carboxylic acids or activated carboxylic acid derivatives VIIa, by reaction with an 35 amine of the formula IVa, in accordance with the following scheme.
00~0/45204 2 1 9 9 i 2 2 ~ CH(UR')-CO-L + H2NR"
Xn ~ R
VIIa VIa Xn~ CH(UR')-Co-NHR~
I (V=NH) In the formula VIIa, L is, for example, halogen (in particular 15 chlorine, bromine or iodine), l-imidazolyl, hydroxyl or f Cl-C4-alkoxy.
The starting compounds in which L is hydroxyl can be prepared by known processes ~cf. Houben-Weyl, vol. E5, pages 223-254; Org.
20 Reactions ~ (1976), 187-224] from the corresponding alkyl esters (L e Cl--C4--alkoxy ) ~
The acyl halides (L = halogen) and imidazolides (L = 1-imidazolyl) are likewise obtained in a known manner tcf.
25 Houben-Weyl, vol. E5, pages 941-977 and pages 983-991, respectively; Houben-Weyl, vol. VIII, page 654 et seq.] from the carboxylic acids (L 5 OH).
Compounds of the formula I in which U is sulfur are obtained, for 30 example, starting from the a-halogen derivatives VII, by reaction with a thiol (R'SH) or with a corresponding thiolate (R'S3) tcf.
J. Org. Chem. 47 (1982), 2882; Can. J. Chem. 57 (1979), 444l, in accordance with the following reaction scheme:
Xn ~ cH(Hal)-covR~ tR~-~3] ~ CH(SR')-COVR'' VII I (U=S) synthesis of the group R
The synthesis of the compounds I can also be carried out by first synthesizing the group -CH(UR')COVR" and then synthesizing the 45 group R. The compound I in which R is alkyl (I.l) is usually used as the starting material, and this compound I.1 is halogenated to 0~50/45~4 21~3122 give the corresponding benzyl halide I.2 [cf. Angew. Chem. 71 (1959), 349].
Xn ~ CH(UR')-COVR [ ; Xn ~ C~(~R')-COVR'' I.l I.2 [Hal = Cl, Br, I]
This halogenation i8 usually carried out at from 0 to 100 C, preferably from 20 to 80 C, in an inert solvent, either in the 15 presence of a free radical initiator (eg. dibenzoyl peroxide or r azobisiso~u~ onitrile) or with UV irradiation, for example using a mercury vapor lamp.
Suitable solvents are aliphatic hydrocarbons, such as pentane, 20 hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, and ethers, such as diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, particularly preferably 25 cyclohexane, methylene chloride and carbon tetrachloride.
Mixtures of the stated solvents may also be used.
The halogenating agents used are, for eY~mrle, elemental halogens (eg. Cl2, ~r2, I2), N-b~ ,osuccinim~de, N-chlorosucc~n;m~de or 30 dibL~ ~ 1methylhydantoin. The halogenating agents are generally f- used in e~uimolar amounts, in excess or, if reguired, as solvents.
The compounds I.2 in whi~h Hal is iodine may furthermore be 35 prepared in a known manner ~J. Chem. Soc. PTI (1976), 416] from the chlorides or bromides by reaction with iodides (eg. sodium iodide) in acetone.
Furthermore, the benzyl halide I.2 is obtained by cleaving a 40 corresponding ether I.3 with a halogenating agent ~Hal].
12 2199~1~2 Xn ~ CH(OR')--C02R'' [Hal]3 Xn ~ CH(OR')--C02R'' CH2--O--R~ CH2--Hal I.3 I.2 [ Ra 5 Alkyl, Aryl] [Hal = Cl, Br]
10 This ether cleavage i8 usually carried out at from -30 to 50 C in an inert solvent.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, 15 such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, alcohols, such as methanol, 20 ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide and dimethylformamide, particularly preferably halogenated and/or aromatic hydrocarbons. Mixtures of the stated solvents may also be used.
25 The halogenating agents used are, for ~A , 1 e, Lewis acids, such as aluminum trichloride, boron trichloride and boron tribromide, or hydrogen halides, such as hydrogen chloride or hydrogen bromide. The halogenating agents are generally used in equimolar amounts or in excess.
~~ The benzyl halide serves as a key intermediate for the preparation of a large number of compounds I according to the following reaction schemes.
35 B.1 R = unsubstituted or substituted alkyl By reacting the benzyl halides I.2 with nucleophi~es, preferably N-, 0- or S-nucleophiles, for example with alcohols, carboxylic acids, thiols or amines, the corresponding ethers, esters, 40 thioethers or amines I.4 are obtained.
~ ' 13 21 99~ 22 ~ " CH(UR')-COVR'' ~ , CH(VR')-COVR'' Xn ~ CH2--Hal + H Y~--A~ Xn ~ CH2--Y~--A
I.2 I.4 In the formulae Y~ is oxygen, sulfur, amino or alkylamino and is unsubstituted or substituted alkyl, acyl or an unsubstituted 10 or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain 15 hetero atoms selected from the group consiting of oxygen, sulfur f and nitrogen.
This reaction i8 usually carried out at from O to 80 C, preferably from 20 to 60 C, in an inert solvent in the presence of a base by 20 standard processes tcf. Organikum, 17th edition, page 172 et seq.
(1988)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, 25 such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydro~uran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl 30 ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and f~- dimethyl sulfoxide and dimethylfor~-m;de, particularly preferably methylene chloride, toluene, acetone, acetonitrile and dimethylformamide. Mixtures of the stated solvents may also be used.
Suitable bases are in general inorganic cv..pounds, such as alkali metal hydroxides and alkaline earth metal hydroxides teg. lithium hydroxide, sodium hydroxide, potassium hydroxide ànd calcium hydroxide), ~lk~l; metal oxides and alkaline earth metal oxides 40 (eg. lithium oxide, sodium oxide, calcium oxide and magnesium oxide), silver oxide, alkali metal hydrides and ~lk~lln~ earth metal hydrides (eg. lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (eg. lithium amide, sodium amide and potassium amide), alkali metal carbonates 45 and alkaline earth metal carbonates (eg. lithium carbonate and calcium carbonate) and ~lk~l; metal bicarbonates (eg. sodium bicarbonate), organometallic compounds, in particular alkali ~ 2199~22 metal alkyls (eg. methyllithium, butyllithium and phenyllithium), alkylmagnesium halides (eg. methylmagnesium chloride) and ~lk~l;
metal alcoholates and alkaline earth metal alcoholates (eg.
sodium methylate, sodium ethylate, potassium ethylate, potaqsium 5 tert-butylate and dimethoxymagnesium), as well as organic bases, for example tertiary amines, such as trimethylamine, triethylamine, triisopropylethylamine and N-méthylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines. Sodium hydroxide, 10 potassium carbonate and potassium tert-butylate are particularly preferred. The bases are generally used in equimolar amounts, in excess or, if required, as solvents.
It may be advantageous for the reaction to add a catalytic amount 15 of a crown ether (eg. 18-crown-6 or 15-crown-5) or from 0.01 to 10% by weight of potassium iodide as a catalyst.
The reaction may also be carried out in two-phase systems consisting of a solution of Al k~l; metal hydroxides, alkaline 20 earth metal hydroxides, Al kAl ~ metal carbonates or Al kAl; ne earth metal carbonates in water and an organic phase (for ~Amrle aromatic and/or halogenated hydrocarbons). Suitable phase transfer catalysts here are, for example, ammonium halides and tetrafluoroborates (eg. benzyltriethylammonium chloride, benzyl 25 tributylammonium bromide, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide or tetrabutylammonium tetrafluoroborate) and phosphonium halides (eg.
tetrabutylphosphonium chloride and tetraphenylphosphonium bromide).
f It may be advantageous for the reaction first to convert H-Y~-Al with the base into the corresponding anion, which is then reacted with the benzyl derivative.
35 B.2 R = substituted or unsubstituted alkenyl By phosphorylating the benzyl halides I.2 and then subjecting the phosphorous compounds I.5 to a Wittig or Wittig-Horner reaction with aldehydes, the corresponding ethylene derivatives I.6 are 40 obtained.
2199~22 Xn ~ C3(UR )--COVR'l P ~3 ~ Xn ~ C3~UR')--COVR'' ( )3~
I.2 IXb I.5 ~" CHtUR')-COVR'' ~ CH(UR')-COVR'' Xn ~ C~2- ~ O-CH-Al Xn ~ CH=CH-A
I.5 I.6 ~- In the formula IXa, ~ is aryl, in particular phenyl; in the formula IXb, Rx is alkyl or aryl, in particular Cl-C4-alkyl or phenyl.
In the formulae X and I.5, Al is unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and 25 nitrogen, or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
30 The reaction of the halides I.2 with the phosphines IXa or the phosphites IXb is carried out in a manner known per se tcf.
Houben-Weyl, 4th edition, vol. XII/1, page 79 et seq. ~nd page 433 et se~. (1963)~.
35 The starting materials I.2 and IXa or IXb are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IXa or IXb in excess, based on I.2.
The phosphorus derivatives I.5 thus obtained are then subjected to a Wittig or a Wittig-Horner reaction with an aldehyde of the formula X at from -30 to 60 C, preferably from O to 40-C, in an inert solvent in the presence of a base.
Suitable solvents are aliphatic hydrocarbons, such as pentane, 45 hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 219~4~2 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, 5 n-butanol and tert-butanol, and dimethyl sulfoxide and dimethylformamide, particularly preferably diethyl ether, tetrahydrofuran, dimethyl sulfoxide and dimethylformamide.
Mixtures of the stated solvents may also be used.
10 Suitable bases are in general inorganic compounds, for e~mple ~1 k~1; metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydrox$de, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides, such as lithium oxide, sodium oxide and calcium oxide, 15 A1 k~l; metal hydrides and ~1 kP1; ne earth metal hydrides, such as sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates, such as lithium carbonate and calcium carbonate, and 20 alkali metal bicarbonates, such as sodium bicarbonate, organometallic co~ uunds, in particular A1 k71; metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride and alkali metal alcoholates and alkaline earth metal alcoholates, such as sodium 25 methylate, sodium ethylate, potassium ethylate, potassium tert-butylate and dimethoxymagnesium, as well as organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 30 4-dimethylaminopyridine, and bicyclic amines. Sodium methylate, ~-- potassium tert-butylate, sodium hydride, potassium carbonate and n-butyllithium are particularly preferred. The bases are ' generally used in eguimolar amounts but may also be used in excess or, if required, as solvents.
The starting materials I.5 and X are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use X in excess, based on I.5.
40 In a modification of the above process, the co...pGunds I.6 are obtained by first oxidizing the benzyl halide I.2 to the corresponding benzaldehyde I.7 and then subjecting I.7 to a Wittig or Wittig-Horner reaction with a phosphorus cor..~uullt Xa or Xb.
CH(UR')-COVR'' Xn ~ CH(UR')--COVR''[OX] ~ X ~ CH=O
CH2-Hal I.2 I.7 Xn ~ CH(UR )--COVR''~3P~ CH2AlHal~ ~ CH(UR')--COVR'' CHzO ~RXO)2P-CH2-Al CH=CH-A
I.7 Xb I.6 The oxidizing agent [OX] used is, for example, methylmorpholine N-oxide monohydrate (cf. EP-A 393 428) or dimethyl sulfoxide ~cf.
J. Chem. Soc. 1964, 520; J. Org. Chem. ~ (1959), 1792].
20 The subsequent Wittig or Wittig-Horner reaction is effected under the conditions described above.
B.3 R - organic radical bonded via oxy, mercapto or amino 25 Compounds I, in which R is an organic radical bonded via an oxy, mercapto or amino group are obtained from the corresponding derivatives I.8 according to the following reaction scheme.
~ CH(UR')-COVR'' Xn ~ CH(UR')-COVR'' I.8 I.9 In the formulae I.8 and I.9, Y~ is oxygen, sulfur, amino or alkylamino and A1 has the abovementioned ~e~n; ngs .
In the formula XI, Ll i8 a nucleophilically sub~titutable leaving 40 group, such as halogen, (eg. chlorine, bromine or iodine), alkanesulfonate or arylsulfonate (eg. methanesulfonate, trifluoromethanesulfonate, phenylsulfonate or 4-methylphenylsulfonate).
45 This reaction is usually carried out in an inert solvent in the presence of a base and in the presence or abQence of a transition metal catalyst in the form of an Ullmann reaction ~cf. Russ.
2199~22 Chem. Rev. 43 (1974), 679 ; J. org. Chem. 29 (1964), 977] or in the form of a nucleophilic substitution reaction [cf.
J. Chem. Soc. (1942), 381; J. Heterocycl. Chem. 1~ (1978), 1513].
5 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 10 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as aceton, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, particularly preferably acetone and dimethylformamide. Mixtures of the stated solvents 15 may also be used.
~..
The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use L1-Al in an excess or in less than stoichiometric amount, based on 20 I.8.
B.4 R = -cRa=N-za-A2 Co,..~ounds I in which R is a group -CRazN-ZA A2 are obtained, for 25 example from the corresponding ketones I.10, by reaction with an O-substituted hydroxylamine or hydroxylammonium salt or a hydrazine or hydrazonium salt by the methods described in EP-A 499 823, according to the following reaction scheme.
~ CH ( UR ' )--COVR ' ' Xn~H ( UR ' )--COVR ' ' xn r o + H2za A2 ~ r N-Z--a_A2 I.10 I.ll In the formulae I.10 and I.ll, 40 Ra is hydrogen, alkyl, haloalkyl or substituted or unsubstituted aryl;
za is oxygen, amino or alkylamino;
45 A2 is hydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl, or ~ lg 2199~22 a substituted or unsubstituted saturated or partially unsaturated cyclic radi~al which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or s a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction conditions correspond in general and in particular to the conditions described in the stated literature.
The ketones I.10 ( Ra ~ H) are obtained from the aldehydes I.7 by 15 oxidation to the carboxylic acids tcf. Organikum, 15th edition, 447 (1977)~, conversion of the carboxylic acids into the corresponding acyl halides ~cf. Organikum, 15th edition, 526 (1977)] and subsequent reaction with organozinc compounds ~cf.
Org. React. (8) (1954~, 28].
B.5 R = -CHRc-o-NscRb-A3 Compounds I in which R is a group -CHRC-o-N=CRb-A3 are obtained, for ~YAmrle~ from benzyl halides I.2, by reaction with a 25 hydrox;i ml ne XII by the methods described in EP-A 354 571, EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 472 300, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO- A 92/18,494, WO-A 93/16,986 and JP-A 05/201,946, according to the following reaction scheme.
X ~ CHtUR')-CO~R'' Xn ~ CH(UR')-COVR'' n ~ + HONsCRb_A3~ ~ CHRCoN=cRb-A3 CHRC-Hal I.2 XIII I.12 In the form~ e I.2, XII and I.12, 40 Rb i8 hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
Rc is hydrogen, alkyl or cycloalkyl;
A3 is substituted or unsubstituted alkyl, alkenyl or alkynyl, or 21 9~'122 a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction conditions correspond in general and in particular to the conditions described in the stated literature.
15 B.6 R = -cHRf-oN=cRe-cRd-No-A4 Compounds I in which R is a group -CHRf-oN=cRe-cRd-No-A4 are obtained, for example from the benzyl halides I.2, by reaction with a dioxime XIV by the methods described in German Application 20 No. P 44 21 180.5, German Application No. P 44 21 181.3 and German Application No. P 44 21 182.1, according to the following reaction scheme.
~" CH(UR')-COVR'' Xn ~ + HoN=cRe-cRdeNo-A4 CHRf--Hal I . 2 XIII
r CH(UR' )--COVR' ' Xn~
CEIRf--ON=CRe--CRd=N~A4 I.13 In the formulae I.2, XI~ and I.13, Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
rf is hydrogen, alkyl or cycloalkyl and 45 A4 is substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially ~ 21 2 1 9 g l 2 2 unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or s a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (eg. sodium hydride, sodium hydroxide, potassium carbonate or triethylamine) by the methods described in Houben-Weyl, vol. E14b, page 370 et seq., 15 and Houben-Weyl, vol. 10/1, page 1189 et seq.
The required dioxime XIV is obtained according to the following scheme:
HON2CRe--CRd=NOH ~ ~2--A4~ HoN=CRe-cRd=No-A4 XV XVI XIV
In the ~ormula XVI, L2 i8 a nucleophilically ~ubstitutable leaving group, for example halogen or a sulfonate group, preferably 25 chlorine, bromine, iodine, methanesulfonate, trifluoromethanesulfonate, phenylsulfonate or 4-methylphenylsulfonate.
The reaction is carried out in a manner known per se in an inert 30 organic solvent in the presence of a base (eg. potassium f carbonate, potasQium hydroxide, sodium hydride, pyridine or triethylamine) by the methods described in Houben-Weyl, vol.
E14b, page 307 et seq., page 370 et seq. and page 385 et seq., Houben-Weyl vol. 10/4, page 55 et seq., page 180 et seq. and page 35 217 et seq., and Houben-Weyl, vol. E5, page 780 et seq.
The dioxime XIV is obtained in a 5;m; 1 ~r manner by reacting the corresponding ketoY~ - XVII with an 0-substituted hydroxylamine or its salt (XVIII) according to the following reaction scheme.
0050/45204 2 ~ 9 9 1 2 2 I H2N~A4 HON=CR~--CRd=O + ~ bzw. ~ , HON=CRe--CRd=NO--A4 XVII H3~ o-A4~ XIV
XVIII
In the formula XVIII, Q~ is the anion of an acid, in particular lO of an inorganic acid (for example halide, such as chloride or bromide).
.
The reaction is carried out in a manner known per se in an inert organic solvent by the methods described in EP-A 513 580, 15 Houben-Weyl vol. 10~4, page 73 et seq., or Houben-Weyl vol. E14b, f page 369 et seg. and page 385 et seq.
Alternatively, the co...~Gunds I.13 are also obtained by first reacting the benzyl halide I.2 with the dioxime XV to give the 20 corresponding benzyloxime I.14 and then converting I.14 with a compound XVI into I.13.
~ CH(UR')-COVR'' 25 Xn ~ ~ HON=CRQ--CRd=NOH
CHRf-Hal I.2 XV
t~ ~" CH(UR')-COVR'' n~
CHRf--ON=CRe--CRd=NOH
I.14 L2-A4 ~ CH(UR')-COVR'' XVI n ~
CHRf--ON=CRe--CRd=NO--A4 I.13 The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or 45 triethylamine) by the methods described in Houben-Weyl, vol.
10/1, page 1189 et seq., Houben-Weyl, vol. E14b, page 307 et seq., page 370 et seq. and page 385 et seq., Houben-Weyl, vol.
0050/4520~
21~9~2 Alkyl phenylacetates The present invention relates to alkyl phenylacetates of the 5 formula I
Xn ~ CH(UR')-COVR'' (I) R
where 15 R' is formyl, Cl-C4-alkylcarbonyl or Cl-C4-alkyl;
R" is C1-C4-alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
~ is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or where n is ~ 1, a C3-Cj-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon ~ , ~ atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, Cl-C4-alkyl, Cl-C4-haloaLkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > l; ~
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or an organic radical which is bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino grou~
or, ~ 2 2199~22 together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
Processes and intermediates for their preparation and their use.
10 Alkyl phenylacetates are disclosed in the literature as drugs or inte -~;ate~ for their preparation lEP-A 486 011, EP-A 462 531, JP - A 03/~84,665, FR-A ~ 572 076, EP - A 166 650, JP-A S9/164,766, JP - A 56/005,439, DE - A 29 31 735, DE - A 24 49 990, JP-A 49/108,039, US - A 3,607,941, GB - A 1 230 347, DE - A 12 77 127, EP - A 065 874, 15 NL - A 75/13,439, NL - A 73/09,425, BE - A 77/06,316, FR-A 2 054 532, , EP-A 565 965, WO-A 91/17,987 and US-A 4,752,616]. In addition, EP-A 206 772 describes such compounds having herbicidal properties and US-A 3,544,304 describes similar com~ounds having growth-regulating properties.
It is an object of the present invention to provide novel compounds having fungicidal properties.
We have found that this object is achieved by the compounds I
25 defined at the outset. We have also found processes and intermediates for their preparation and their use for controlling ~n; ~1 pests or harmful fungi.
The comp~unds I are prepared by methods similar to various 30 methods known per se from the literature. In the preparation, it is not important whether the group R or the group -CH~UR')-COVR"
is synthesized first.
These groups are particularly advantageously obtained by the 35 processes described below.
A synthesis of the group -CH(UR')-COVR":
The compounds I in which U and V are each oxygen are obtained, 40 for example, by converting a benzaldehyde of the formula II with a cyanide in the manner known per se into the corresponding cyanohydrin of the formula III, hydrolyzing III in the presence of an acid with an alcohol of the formula IV to give the corresponding alkyl ~-hydroxyphenylacetate of the formula V and 45 etherifying V with a derivative of the formula VIa to give I.
~" CHO CH(OH)-CN
Xn ~ + HCN ~ Xn ~ R
II III
~ CH ( OH )--C02R ' ' 10rH+l/R''OH Xn ~ R
IV V
~ " CH(OR')-C02R'' R'-Ll~ Xn ~
R
( VIa In the formula VIa, Ll is a nucleophilically substitutable leaving 20 group, such as halogen teg. chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate)~
25 The cyanohydrin III is prepared in a manner known per se ~cf.
organikum, 15th edition (1977), page 557 et seq.; Houben-Weyl vol. VIII, 274 et se~. (1952)], usually at from O to 40 C, preferably from O to 20 C, without a solvent, in water or in an inert solvent, if necessary with phase transfer catalysis.
- Suitable HCN sources are hydrocyanic acid itself and cyanides, from which HCN is formed by the addition of a mineral acid.
Particularly suitable cyanides are ~l k~l; metal cyanides (eg.
35 potassium cyanide or sodium cyanide)O
The cyanides or HCN are used in general in equimolar amounts. It may be advantageous for the yield to use an excess of from 10 to 20 mol%, based on benzaldehyde II.
Suitable solvents are water, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, suc as methylene chloride, chloroform and 45 chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, 2199i~2~
n-butanol and tert-butanol, particularly preferably water and/or alcohols. Mixtures of the stated solvents may also be used.
When cyanides are used, the reaction is usually carried out by 5 gradually adding equimolar amounts of a mineral acid (for ~x~mple a hydrohalic acid, such as hydrochloric acid or hydrobromic acid, sulfuric or phosphoric acid). Instead of the mineral acids, equimolar amounts of acidic salts (es. ammonium chloride or ammonium sulfate) are also used. The acids or acidic salts are 10 generally used in equimolar amounts, based on cyanide.
For example, alkali metal cyanides, alkali metal carbonates, ammonia or organic bases, such as alkylamines and alcoholates, are used as basic catalysts.
i The benzaldehydes II required for the preparation of the compounds I are known in the literature (EP-A 400 417) or can be prepared according to the cited literature.
20 The hydrolysis of the cyanohydrins III to give the corresponding alkyl a-hydroxyphenylacetates of the formula V is carried out in a manner known per se [Org. Synth. Col. Vol. I (1941) 336;
US-A 2,892,847; EP-A 400 417], usually at from O to 100 C, preferably from 10 to 50 C, in the presence of an acid and R"OH as 25 a solvent. If required, an inert solvent may additionally be used. In order to liberate the cG~ ounds V from the iminoesters formed as intermediates, it is necessary to add water.
Suitable inert solvents are aliphatic hydrocarbons, such as 30 pentane, hexane, cyclohexane and petroleum ether, aromatic _ hydrocarbons, such as toluene, o-, m- and p-xylene, ( halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, 35 ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide. Mixtures of the stated solvents may also be used.
40 The acids and acidic catalysts used are inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sul~uric acid and perchloric acid, in particular hydrochloric acid and sulfuric acid. The acids are generally used in equimolar amounts.
With regard to the yield, it may be advantageous to add an excess 45 of acid.
005~/452~4 2199~22 The alkyl a-hydroxyacetates thus obtained are then etheri~ied with a derivative of the formula VIa in a manner known per se tJ-Chem. Soc. (1899), 753; Austr. J. Chem. 43 (1990), 2045; J. Org.
Chem. 47 (1982), 5404] in the presence of a base to give the 5 compounds I.
This reaction is usually carried out at from O to 80 C, preferably from O to 30-C, in an inert ~olvent.
10 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 15 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, particularly preferably tetrahydrofuran and dimethylformamide. Mixtures of the stated 20 solvents may also be used.
Suitable bases are in general inorganic ~vmpounds, such as Alk~i metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and 25 calcium hydroxide, alkali metal oxides and alkAl~nP earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, ?1 k~l; metal hydrides and ~1 kAl ~ ne earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, ~lk~l i metal amides, such as lithium 30 amide, sodium amide and potassium amide, ~lkal; metal carbonates and alk~li n~ earth metal carbonates, such as lithium carbonate and calcium carbonate, and alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and 35 phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and Al k~l ~ metal alcoholates and Al k~l;ne earth metal alcoholates, such as sodium methylate, sodium ethylate, potassium ethylate, potassium tert-butylate and dimethoxymagnesium, as well as inorganic bases, for ~F~mrle tertiary amines, such as 40 trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines. Sodium hydride is particularly preferred. The bases are used in general in equimolar amounts. However, they may also be 45 used in excess or, if required, as solvents.
:
0050/452~4 2199~22 In a modification of the process described above, the c~ Gunds of the formula I are obtained starting from the alkyl a-hydroxyphenylacetates of the formula V also by first converting the compounds V with a halogenating agent in a manner known per 5 se into the corresponding alkyl ~-halophenylacetate and then etherifying VII in the presence of a base with an alcohol of the formula VIb to give I.
Xn ~ C~OH)-C02R" tHal] X~ ~ C~(Hal)-C02R'' V VII
f ~" CH(OR')--C02R'' R'-OH~ Xn ~ R
VIb In the formula VII, Hal is halogen, in particular chlorine, bromine or iodine.
25 The halogenation of the cor~.~ounds V is carried out in a manner known per se tcf. Chem. Ber. 120 (1987), 1825], usually at from O
to 60-C, preferably from 10 to 30 C.
Suitable halogenating agents are phosphoryl bromide, phosphoryl 30 chloride, thionyl chloride, tetrab~l --thane/triphenylphosphine, boron tribromide and hydrogen bromide. An excess of the halogenating agents is generally used. The reaction i8 carried out in general in an inert solvent.
35 Suitable inert solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ethe~, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, ch~oroform and chlorobenzene, ethers, such as diethyl ether, diiso~rGpyl ether, 40 tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide 45 and dimethylformamide, and inert organic amines, such as ~050/45~4 2199~22 triethylamine and pyridine, particularly preferably toluene and acetonitrile. Mixtures of the stated solvents may also be used.
Alternatively, the aldehydes of the formula II may also be 5 converted by base-catalyzed condensation with a haloform (eg.
chloroform or bromoform) and with an alcohol of the formula R'OH
in a manner known per se tcf. J. Am. Chem. Soc. 82 (1960), 406Z]
into the corresponding a-alkoxyphenylacetic acids, from which the esters of the formula I (U = V = O) are obtainable by known 10 methods, either directly or via activated carboxylic acid derivatives.
CHO R'OH/Base 15 Xn ~ + CHHal3 20 ~ CH(OR')-~O2H
Xn ~ ~ OH(OR')-CO2R"
R R"OH ~ Xn ~ R
I (U = V = o) In a further process, the c~..~ounds I are obtained starting from alkyl a-ketophenylacetates of the formula VIII by reduction to the corresponding alkyl a-hydroxyphenylacetates of the formula V
and subsequent conversion of V into I by the processes described 30 above.
Xn ~ C(=0)--CO2R'' [H~ Xn ~ CH(OH)--C02R'' VIII V
The reduction of the alkyl a-ketophenylacetates'VIII i8 carried out in a manner known per se ~J. Chem. Soc. (1954), 520; Chem.
40 ~er. 76 (1943), 308; Chem. Ber. l~Q (1987), 1825], usually at from -100 to 100 C, preferably from 0 to 30 C, in an inert solvent.
~Amrles of suitable reducing agents are hydrides (eg. sodium 45 borohydride) and hydrogen.
2199~22 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as 5 diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, organic acids, such as acetic acid, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide 10 and dimethylformamide, particularly preferably methanol and tetrahydrofuran. Mixtures of the stated solvents may also be used.
The reduction with hydrogen is usually carried out in the 15 presence of a catalyst, such as nickel, Raney nickel, palladium ( or palladium on a carrier such as carbon.
The alkyl ~-ketocarboxylates of the formula VII which are required for this preparation process are known in the literature 20 (EP-A 206 606, EP-A 226 ~17, EP-A 242 081, EP-A 253 213, EP-A 256 667, EP-A 267 734, EP-A 278 595, EP-A 307 101, EP-A 307 103, EP-A 310 954, EP-A 335 519, EP-A 341 845, EP-A 350 691, EP-A 354 571, EP-A 363 818, EP-A 370 629, EP-A 373 775, EP-A 378 755, EP-A 382 375, EP-A 386 561, 25 EP-A 393 861, EP-A 407 873, EP-A 414 153, EP-A 426 460, EP-A 459 285, EP-A 460 575, EP-A 468 684, EP-A 472 224, EP-A 472 300, EP-A 474 042, EP-A 475 158, EP-A 480 795, EP-A 499 823, EP-A 528 245, EP-A 538 097, EP-A 564 928, EP-A 579 124, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830, 30 Wo-A 92/19,487, WO-A 92/18,494, WO-A 93/16,986, WO-A 94/11,334, JP-A 05/201,946, German Application No. P 43 05 502.8, German Application No. P 44 21 180.5, German Application No.
P 44 21 181.3 and German Application No. P 44 21 182.1) or can be prepared according to the literature cited.
The compounds of the formula I in which U is amino and V is oxygen are prepared, for example, by reacting a compound of the formula VII with a primary amine or a corresponding ammonium salt of the formula VIc in a manner known per se (~S-A 4,723,031).
0050l4S~U~
-- 9 21~9~22 ~ " CH(Hal)-CO2R" + H2NR' or salt Xn ~ R
VII VIc CH(NHR')-CO2R"
; Xn ~ R
I (U=NH, V=O) The compounds I in which U is aminooxy and V is oxygen are 15 obtained in a S; m~ 1 ~r manner by reacting VII with O-alkylhy~G~ylamines or with the corresponding hydroxylammonium salts VId.
Xn ~ CH(H~ CO2R" + H2NOR' or salt VII VId CH(NHOR')-C02R"
Xn~
R
I (U=NH-O-, V=o) ~ ' ' ~ .
Compounds I in which V is amino are obtained, for example, starting from the corresponding esters, carboxylic acids or activated carboxylic acid derivatives VIIa, by reaction with an 35 amine of the formula IVa, in accordance with the following scheme.
00~0/45204 2 1 9 9 i 2 2 ~ CH(UR')-CO-L + H2NR"
Xn ~ R
VIIa VIa Xn~ CH(UR')-Co-NHR~
I (V=NH) In the formula VIIa, L is, for example, halogen (in particular 15 chlorine, bromine or iodine), l-imidazolyl, hydroxyl or f Cl-C4-alkoxy.
The starting compounds in which L is hydroxyl can be prepared by known processes ~cf. Houben-Weyl, vol. E5, pages 223-254; Org.
20 Reactions ~ (1976), 187-224] from the corresponding alkyl esters (L e Cl--C4--alkoxy ) ~
The acyl halides (L = halogen) and imidazolides (L = 1-imidazolyl) are likewise obtained in a known manner tcf.
25 Houben-Weyl, vol. E5, pages 941-977 and pages 983-991, respectively; Houben-Weyl, vol. VIII, page 654 et seq.] from the carboxylic acids (L 5 OH).
Compounds of the formula I in which U is sulfur are obtained, for 30 example, starting from the a-halogen derivatives VII, by reaction with a thiol (R'SH) or with a corresponding thiolate (R'S3) tcf.
J. Org. Chem. 47 (1982), 2882; Can. J. Chem. 57 (1979), 444l, in accordance with the following reaction scheme:
Xn ~ cH(Hal)-covR~ tR~-~3] ~ CH(SR')-COVR'' VII I (U=S) synthesis of the group R
The synthesis of the compounds I can also be carried out by first synthesizing the group -CH(UR')COVR" and then synthesizing the 45 group R. The compound I in which R is alkyl (I.l) is usually used as the starting material, and this compound I.1 is halogenated to 0~50/45~4 21~3122 give the corresponding benzyl halide I.2 [cf. Angew. Chem. 71 (1959), 349].
Xn ~ CH(UR')-COVR [ ; Xn ~ C~(~R')-COVR'' I.l I.2 [Hal = Cl, Br, I]
This halogenation i8 usually carried out at from 0 to 100 C, preferably from 20 to 80 C, in an inert solvent, either in the 15 presence of a free radical initiator (eg. dibenzoyl peroxide or r azobisiso~u~ onitrile) or with UV irradiation, for example using a mercury vapor lamp.
Suitable solvents are aliphatic hydrocarbons, such as pentane, 20 hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, and ethers, such as diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, particularly preferably 25 cyclohexane, methylene chloride and carbon tetrachloride.
Mixtures of the stated solvents may also be used.
The halogenating agents used are, for eY~mrle, elemental halogens (eg. Cl2, ~r2, I2), N-b~ ,osuccinim~de, N-chlorosucc~n;m~de or 30 dibL~ ~ 1methylhydantoin. The halogenating agents are generally f- used in e~uimolar amounts, in excess or, if reguired, as solvents.
The compounds I.2 in whi~h Hal is iodine may furthermore be 35 prepared in a known manner ~J. Chem. Soc. PTI (1976), 416] from the chlorides or bromides by reaction with iodides (eg. sodium iodide) in acetone.
Furthermore, the benzyl halide I.2 is obtained by cleaving a 40 corresponding ether I.3 with a halogenating agent ~Hal].
12 2199~1~2 Xn ~ CH(OR')--C02R'' [Hal]3 Xn ~ CH(OR')--C02R'' CH2--O--R~ CH2--Hal I.3 I.2 [ Ra 5 Alkyl, Aryl] [Hal = Cl, Br]
10 This ether cleavage i8 usually carried out at from -30 to 50 C in an inert solvent.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, 15 such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, alcohols, such as methanol, 20 ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide and dimethylformamide, particularly preferably halogenated and/or aromatic hydrocarbons. Mixtures of the stated solvents may also be used.
25 The halogenating agents used are, for ~A , 1 e, Lewis acids, such as aluminum trichloride, boron trichloride and boron tribromide, or hydrogen halides, such as hydrogen chloride or hydrogen bromide. The halogenating agents are generally used in equimolar amounts or in excess.
~~ The benzyl halide serves as a key intermediate for the preparation of a large number of compounds I according to the following reaction schemes.
35 B.1 R = unsubstituted or substituted alkyl By reacting the benzyl halides I.2 with nucleophi~es, preferably N-, 0- or S-nucleophiles, for example with alcohols, carboxylic acids, thiols or amines, the corresponding ethers, esters, 40 thioethers or amines I.4 are obtained.
~ ' 13 21 99~ 22 ~ " CH(UR')-COVR'' ~ , CH(VR')-COVR'' Xn ~ CH2--Hal + H Y~--A~ Xn ~ CH2--Y~--A
I.2 I.4 In the formulae Y~ is oxygen, sulfur, amino or alkylamino and is unsubstituted or substituted alkyl, acyl or an unsubstituted 10 or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain 15 hetero atoms selected from the group consiting of oxygen, sulfur f and nitrogen.
This reaction i8 usually carried out at from O to 80 C, preferably from 20 to 60 C, in an inert solvent in the presence of a base by 20 standard processes tcf. Organikum, 17th edition, page 172 et seq.
(1988)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, 25 such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydro~uran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl 30 ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and f~- dimethyl sulfoxide and dimethylfor~-m;de, particularly preferably methylene chloride, toluene, acetone, acetonitrile and dimethylformamide. Mixtures of the stated solvents may also be used.
Suitable bases are in general inorganic cv..pounds, such as alkali metal hydroxides and alkaline earth metal hydroxides teg. lithium hydroxide, sodium hydroxide, potassium hydroxide ànd calcium hydroxide), ~lk~l; metal oxides and alkaline earth metal oxides 40 (eg. lithium oxide, sodium oxide, calcium oxide and magnesium oxide), silver oxide, alkali metal hydrides and ~lk~lln~ earth metal hydrides (eg. lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (eg. lithium amide, sodium amide and potassium amide), alkali metal carbonates 45 and alkaline earth metal carbonates (eg. lithium carbonate and calcium carbonate) and ~lk~l; metal bicarbonates (eg. sodium bicarbonate), organometallic compounds, in particular alkali ~ 2199~22 metal alkyls (eg. methyllithium, butyllithium and phenyllithium), alkylmagnesium halides (eg. methylmagnesium chloride) and ~lk~l;
metal alcoholates and alkaline earth metal alcoholates (eg.
sodium methylate, sodium ethylate, potassium ethylate, potaqsium 5 tert-butylate and dimethoxymagnesium), as well as organic bases, for example tertiary amines, such as trimethylamine, triethylamine, triisopropylethylamine and N-méthylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines. Sodium hydroxide, 10 potassium carbonate and potassium tert-butylate are particularly preferred. The bases are generally used in equimolar amounts, in excess or, if required, as solvents.
It may be advantageous for the reaction to add a catalytic amount 15 of a crown ether (eg. 18-crown-6 or 15-crown-5) or from 0.01 to 10% by weight of potassium iodide as a catalyst.
The reaction may also be carried out in two-phase systems consisting of a solution of Al k~l; metal hydroxides, alkaline 20 earth metal hydroxides, Al kAl ~ metal carbonates or Al kAl; ne earth metal carbonates in water and an organic phase (for ~Amrle aromatic and/or halogenated hydrocarbons). Suitable phase transfer catalysts here are, for example, ammonium halides and tetrafluoroborates (eg. benzyltriethylammonium chloride, benzyl 25 tributylammonium bromide, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide or tetrabutylammonium tetrafluoroborate) and phosphonium halides (eg.
tetrabutylphosphonium chloride and tetraphenylphosphonium bromide).
f It may be advantageous for the reaction first to convert H-Y~-Al with the base into the corresponding anion, which is then reacted with the benzyl derivative.
35 B.2 R = substituted or unsubstituted alkenyl By phosphorylating the benzyl halides I.2 and then subjecting the phosphorous compounds I.5 to a Wittig or Wittig-Horner reaction with aldehydes, the corresponding ethylene derivatives I.6 are 40 obtained.
2199~22 Xn ~ C3(UR )--COVR'l P ~3 ~ Xn ~ C3~UR')--COVR'' ( )3~
I.2 IXb I.5 ~" CHtUR')-COVR'' ~ CH(UR')-COVR'' Xn ~ C~2- ~ O-CH-Al Xn ~ CH=CH-A
I.5 I.6 ~- In the formula IXa, ~ is aryl, in particular phenyl; in the formula IXb, Rx is alkyl or aryl, in particular Cl-C4-alkyl or phenyl.
In the formulae X and I.5, Al is unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and 25 nitrogen, or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
30 The reaction of the halides I.2 with the phosphines IXa or the phosphites IXb is carried out in a manner known per se tcf.
Houben-Weyl, 4th edition, vol. XII/1, page 79 et seq. ~nd page 433 et se~. (1963)~.
35 The starting materials I.2 and IXa or IXb are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IXa or IXb in excess, based on I.2.
The phosphorus derivatives I.5 thus obtained are then subjected to a Wittig or a Wittig-Horner reaction with an aldehyde of the formula X at from -30 to 60 C, preferably from O to 40-C, in an inert solvent in the presence of a base.
Suitable solvents are aliphatic hydrocarbons, such as pentane, 45 hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 219~4~2 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, 5 n-butanol and tert-butanol, and dimethyl sulfoxide and dimethylformamide, particularly preferably diethyl ether, tetrahydrofuran, dimethyl sulfoxide and dimethylformamide.
Mixtures of the stated solvents may also be used.
10 Suitable bases are in general inorganic compounds, for e~mple ~1 k~1; metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydrox$de, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides, such as lithium oxide, sodium oxide and calcium oxide, 15 A1 k~l; metal hydrides and ~1 kP1; ne earth metal hydrides, such as sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates, such as lithium carbonate and calcium carbonate, and 20 alkali metal bicarbonates, such as sodium bicarbonate, organometallic co~ uunds, in particular A1 k71; metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride and alkali metal alcoholates and alkaline earth metal alcoholates, such as sodium 25 methylate, sodium ethylate, potassium ethylate, potassium tert-butylate and dimethoxymagnesium, as well as organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 30 4-dimethylaminopyridine, and bicyclic amines. Sodium methylate, ~-- potassium tert-butylate, sodium hydride, potassium carbonate and n-butyllithium are particularly preferred. The bases are ' generally used in eguimolar amounts but may also be used in excess or, if required, as solvents.
The starting materials I.5 and X are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use X in excess, based on I.5.
40 In a modification of the above process, the co...pGunds I.6 are obtained by first oxidizing the benzyl halide I.2 to the corresponding benzaldehyde I.7 and then subjecting I.7 to a Wittig or Wittig-Horner reaction with a phosphorus cor..~uullt Xa or Xb.
CH(UR')-COVR'' Xn ~ CH(UR')--COVR''[OX] ~ X ~ CH=O
CH2-Hal I.2 I.7 Xn ~ CH(UR )--COVR''~3P~ CH2AlHal~ ~ CH(UR')--COVR'' CHzO ~RXO)2P-CH2-Al CH=CH-A
I.7 Xb I.6 The oxidizing agent [OX] used is, for example, methylmorpholine N-oxide monohydrate (cf. EP-A 393 428) or dimethyl sulfoxide ~cf.
J. Chem. Soc. 1964, 520; J. Org. Chem. ~ (1959), 1792].
20 The subsequent Wittig or Wittig-Horner reaction is effected under the conditions described above.
B.3 R - organic radical bonded via oxy, mercapto or amino 25 Compounds I, in which R is an organic radical bonded via an oxy, mercapto or amino group are obtained from the corresponding derivatives I.8 according to the following reaction scheme.
~ CH(UR')-COVR'' Xn ~ CH(UR')-COVR'' I.8 I.9 In the formulae I.8 and I.9, Y~ is oxygen, sulfur, amino or alkylamino and A1 has the abovementioned ~e~n; ngs .
In the formula XI, Ll i8 a nucleophilically sub~titutable leaving 40 group, such as halogen, (eg. chlorine, bromine or iodine), alkanesulfonate or arylsulfonate (eg. methanesulfonate, trifluoromethanesulfonate, phenylsulfonate or 4-methylphenylsulfonate).
45 This reaction is usually carried out in an inert solvent in the presence of a base and in the presence or abQence of a transition metal catalyst in the form of an Ullmann reaction ~cf. Russ.
2199~22 Chem. Rev. 43 (1974), 679 ; J. org. Chem. 29 (1964), 977] or in the form of a nucleophilic substitution reaction [cf.
J. Chem. Soc. (1942), 381; J. Heterocycl. Chem. 1~ (1978), 1513].
5 Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halohydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, 10 dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as aceton, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, particularly preferably acetone and dimethylformamide. Mixtures of the stated solvents 15 may also be used.
~..
The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use L1-Al in an excess or in less than stoichiometric amount, based on 20 I.8.
B.4 R = -cRa=N-za-A2 Co,..~ounds I in which R is a group -CRazN-ZA A2 are obtained, for 25 example from the corresponding ketones I.10, by reaction with an O-substituted hydroxylamine or hydroxylammonium salt or a hydrazine or hydrazonium salt by the methods described in EP-A 499 823, according to the following reaction scheme.
~ CH ( UR ' )--COVR ' ' Xn~H ( UR ' )--COVR ' ' xn r o + H2za A2 ~ r N-Z--a_A2 I.10 I.ll In the formulae I.10 and I.ll, 40 Ra is hydrogen, alkyl, haloalkyl or substituted or unsubstituted aryl;
za is oxygen, amino or alkylamino;
45 A2 is hydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl, or ~ lg 2199~22 a substituted or unsubstituted saturated or partially unsaturated cyclic radi~al which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or s a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction conditions correspond in general and in particular to the conditions described in the stated literature.
The ketones I.10 ( Ra ~ H) are obtained from the aldehydes I.7 by 15 oxidation to the carboxylic acids tcf. Organikum, 15th edition, 447 (1977)~, conversion of the carboxylic acids into the corresponding acyl halides ~cf. Organikum, 15th edition, 526 (1977)] and subsequent reaction with organozinc compounds ~cf.
Org. React. (8) (1954~, 28].
B.5 R = -CHRc-o-NscRb-A3 Compounds I in which R is a group -CHRC-o-N=CRb-A3 are obtained, for ~YAmrle~ from benzyl halides I.2, by reaction with a 25 hydrox;i ml ne XII by the methods described in EP-A 354 571, EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 472 300, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO- A 92/18,494, WO-A 93/16,986 and JP-A 05/201,946, according to the following reaction scheme.
X ~ CHtUR')-CO~R'' Xn ~ CH(UR')-COVR'' n ~ + HONsCRb_A3~ ~ CHRCoN=cRb-A3 CHRC-Hal I.2 XIII I.12 In the form~ e I.2, XII and I.12, 40 Rb i8 hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
Rc is hydrogen, alkyl or cycloalkyl;
A3 is substituted or unsubstituted alkyl, alkenyl or alkynyl, or 21 9~'122 a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction conditions correspond in general and in particular to the conditions described in the stated literature.
15 B.6 R = -cHRf-oN=cRe-cRd-No-A4 Compounds I in which R is a group -CHRf-oN=cRe-cRd-No-A4 are obtained, for example from the benzyl halides I.2, by reaction with a dioxime XIV by the methods described in German Application 20 No. P 44 21 180.5, German Application No. P 44 21 181.3 and German Application No. P 44 21 182.1, according to the following reaction scheme.
~" CH(UR')-COVR'' Xn ~ + HoN=cRe-cRdeNo-A4 CHRf--Hal I . 2 XIII
r CH(UR' )--COVR' ' Xn~
CEIRf--ON=CRe--CRd=N~A4 I.13 In the formulae I.2, XI~ and I.13, Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
rf is hydrogen, alkyl or cycloalkyl and 45 A4 is substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially ~ 21 2 1 9 g l 2 2 unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or s a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (eg. sodium hydride, sodium hydroxide, potassium carbonate or triethylamine) by the methods described in Houben-Weyl, vol. E14b, page 370 et seq., 15 and Houben-Weyl, vol. 10/1, page 1189 et seq.
The required dioxime XIV is obtained according to the following scheme:
HON2CRe--CRd=NOH ~ ~2--A4~ HoN=CRe-cRd=No-A4 XV XVI XIV
In the ~ormula XVI, L2 i8 a nucleophilically ~ubstitutable leaving group, for example halogen or a sulfonate group, preferably 25 chlorine, bromine, iodine, methanesulfonate, trifluoromethanesulfonate, phenylsulfonate or 4-methylphenylsulfonate.
The reaction is carried out in a manner known per se in an inert 30 organic solvent in the presence of a base (eg. potassium f carbonate, potasQium hydroxide, sodium hydride, pyridine or triethylamine) by the methods described in Houben-Weyl, vol.
E14b, page 307 et seq., page 370 et seq. and page 385 et seq., Houben-Weyl vol. 10/4, page 55 et seq., page 180 et seq. and page 35 217 et seq., and Houben-Weyl, vol. E5, page 780 et seq.
The dioxime XIV is obtained in a 5;m; 1 ~r manner by reacting the corresponding ketoY~ - XVII with an 0-substituted hydroxylamine or its salt (XVIII) according to the following reaction scheme.
0050/45204 2 ~ 9 9 1 2 2 I H2N~A4 HON=CR~--CRd=O + ~ bzw. ~ , HON=CRe--CRd=NO--A4 XVII H3~ o-A4~ XIV
XVIII
In the formula XVIII, Q~ is the anion of an acid, in particular lO of an inorganic acid (for example halide, such as chloride or bromide).
.
The reaction is carried out in a manner known per se in an inert organic solvent by the methods described in EP-A 513 580, 15 Houben-Weyl vol. 10~4, page 73 et seq., or Houben-Weyl vol. E14b, f page 369 et seg. and page 385 et seq.
Alternatively, the co...~Gunds I.13 are also obtained by first reacting the benzyl halide I.2 with the dioxime XV to give the 20 corresponding benzyloxime I.14 and then converting I.14 with a compound XVI into I.13.
~ CH(UR')-COVR'' 25 Xn ~ ~ HON=CRQ--CRd=NOH
CHRf-Hal I.2 XV
t~ ~" CH(UR')-COVR'' n~
CHRf--ON=CRe--CRd=NOH
I.14 L2-A4 ~ CH(UR')-COVR'' XVI n ~
CHRf--ON=CRe--CRd=NO--A4 I.13 The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or 45 triethylamine) by the methods described in Houben-Weyl, vol.
10/1, page 1189 et seq., Houben-Weyl, vol. E14b, page 307 et seq., page 370 et seq. and page 385 et seq., Houben-Weyl, vol.
0050/4520~
2~9~l~22 10/4, page 55 et seq., page 180 et seq. and page 214 et seq., and Houben-Weyl, vol. E5, page 780 et seq.
A further possibility for the preparation of the ~...pounds I.13 5 is first to react the benzyl halide of the formula I.2 with N-hydroxyphthalimide, to convert the re~ulting product into the corresponding benzylhydroxylamine (I.15) by hydrazinolysis and then to react I.15 with a ketoxime of the formula XVIIa to give I.13.
O
CH(UR')-COVR ~
Xn ~ CHRf-Hal HO-N ~ ~~~~' ~'" O
I.2 ~" CH(UR'~-COVR'' Xn ~ CHRf-oNpht (Pht = Ph~h~ ;de radical) CH(UR')-C0VR'' H2NNH2 Xn~
CHRf{)NH2 ~ CH(UR')-COVR'' ~' OCR~--CRd--N~A4~
XVIIa CHRf-oN=cRe-~cRd=No-A4 I.13 The conversion of the benzyl halide I.2 into the benzylhydroxylamine I.15 is carried out in a manner known per se in an inert organic solvent by the methods described in 40 EP-A 463 488 and EP-A 585 751.
Compounds I in which R is substituted or unsubstituted alkynyl are obtained from the cG.~.~ounds I.15 (R=halogen, in parti~ular bromine) by a Heck reaction with an acetylene derivative [cf.
45 J. Organomet. Chem. 93 (1975), 259] in the presence of a transition metal catalyst [TM], for example a palladium or nickel co.ll~ound, such as diacetylpalladium, palladium dichloride, .
2199q22 tetra(triphenylphosphine)palladium or nickel dichloride, in an inert solvent (eg. dimethylformamide, acetonitrile, tetrahydrofuran or toluene) and in the presence of a base (eg.
potassium carbonate, sodium hydride, diethylamine, triethylamine 5 or pyridine).
~" CH(UR')-COVR"
Xn ~ ~ H--C_C--Rt R
I.15 (R=Hal) ~ase Xn ~ CH(UR')-COVR~
~ere, Rt i8 hydrogen, substituted or unsubstituted alkyl, a ~ 20 substituted or unsubstituted saturated or partially unsaturated cyclic radial which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring which, in addition to carbon ring - h~rs, may 25 contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
Alkyl phenyl acetates of the formula I, where R is a group Al-Yl-in which yl i8 a direct bond, oxygen, sulfur, amino or alkylamino and Al is substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic r~ng system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are particularly preferred.
219!3422 25Alkyl phenylacetates of the formula I where R is CH2OAl in which Al is in particular a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms ~elected from the 5 group consisting of oxygen, sulfur and nitrogen, or in which Al is in particular a substituted or unsubstituted aromatic ring which, in addition to carbon ~ing members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are also preferred.
Other preferred alkyl phenylacetates are those of the formula I
where R is a group A2-ZaN=CRa- in which Ra is hydrogen, alkyl, haloalkyl or substituted or unsubstituted aryl;
za is oxygen, amino or alkylamino;
A2 is hydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring h~rs, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of f oxygen, sulfur and nitrogen.
.
Alkyl phenylacetates of the formula I where R is a group A3-CRb=NocHRc- in which Rb is hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
40 Rc is hydrogen, alkyl or cycloalkyl;
A3 substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected -~ ~l9g~22 from the gr~up consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are furthermore preferred.
10 Other preferred alkyl phenylacetates are those of the formula I
where R is a group A4-oN=CRd-CRe=No-cHRf- in which Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
Rf is hydrogen, alkyl or cycloalkyl;
A4 substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon xing members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
f Alkyl phenylacetates of the formula I where R and one of the radicals X, together with the phenyl ring to which they are bonded, for~ a substituted or unsubstituted bicyclic structure 35 selected from the group consisting of benzofuran, benzothiophene, indole, isoindole and naphthalene are also particularly preferred.
.
In the definitions of the symbols stated in the above formulae, 40 collective definitions which are representative generally for the following substituents were used:
halogen: fluorine, chlorine, bromine and iodine;
45 alkyl: unsasturated, straight-chain or branched hydrocarbon radicals of 1 to 10 carbon atoms, eg. C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, l-methyl-propyl, 27 219~422 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, l,1-dimethylpropyl, 1,2-dimethylpropyl, l-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 5 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl;
10 haloalkyl: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above), in which some or all of the hydrogen atoms may be.replaced by halogen atoms as above, eg. Cl- or C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 15 chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, ( l-chloroethyl, 1-bromoethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-tri~luoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-~luoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
alkoxy: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an oxygen atom (-O-);
25 haloalkoxy: straight-chain or branched haloalkyl o~ 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an oxygen atom (-0-);
alkylthio: straight-chain or branched alkyl of 1 to 10 or 1 to 4 30 carbon atoms (as stated above) which is bonded to the skeleton f via a sulfur atom (-S-);
alkylamino: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an 35 amino group (-NH-) or which is bonded to the skeleton via a group -NYl- or -NZ a_;
alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any 40 desired position, eg. C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-buten~l, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 45 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-2~99 1~2 propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-l-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 5 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-10 butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-15 1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-f butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
20 alkynyl: straight-chain or branched hydrocarbon groups having 2 to lO carbon atoms and a triple bond in any desired position, eg.
C2-C6-alkynyl, such as ethynyl, l-propynyl, 2 ~L o~y,lyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-25 butynyl, 1-methyl-3-butynyl, 2-methyl-3 bu~yl-ylr 3-methyl-1-butynyl, l,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl- 1-pentynyl, 3-methyl-4-pentynyl, 30 4-methyl 1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, f 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
35 cycloalkyl: monocyclic alkyl of 3 to 12 carbon ring members, eg.
C3-C8-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; ~
saturated or partially unsaturated cyclic radical which, in 40 addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen: cycloalkyl of 3 to 12 carbon ring members as stated above or 5 -~hered or 6 s~hered heterocyclyl cont~;n;ng, in addition to carbon ring members, from 1 to 3 nitrogen atoms 45 and/or 1 or oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrroiidynyl, -21~9~22 ~ 29 3-pyrrolidynyl, 3-isoxazolidynyl, 4-isoxazolidynyl, 5-isoxazolidynyl, 3-isothiazolidynyl, 4-isothiazolidynyl, 5-isothiazolidynyl, 3-pyrazolidynyl, 4-pyrazolidynyl, 5-pyrazolidynyl, 2-oxazolidynyl, 4-oxazolidynyl, 5-oxazolidynyl, 5 2-thiazolidynyl, 4-thiazolidynyl, 5-thiazolidynyl, 2-imidazolidynyl, 4-imidazolidynyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 10 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl, 15 3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 20 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydlo~yL~zol-l-yl~ 2~3-dihydLo~yLazol-2-yl~
2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydLo~y t azol-1-yl, 2~ 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihyd~o~y~azol-1-yl~
4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 30 2,3-dihydrooxazol-5-yl, 3,4-dihydroo~azol-2-yl, f 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihyd~oo~azol-4-yl, 2-piperidynyl, 3-piperidynyl, 4-piperidynyl, 1,3-dioxane-5-yl, 35 2-tetrahyd~o~y-anyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazynyl, 4-tetrahydropyridazynyl, 2-tetrahydropyrimidynyl, 4-tetrahydropyrimidynyl, 5-tetrahydropyrimidynyl, 2-tetrahydropyrazynyl, 1,3,5-tetrahydro-triazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl;
aryl: a mononuclear to trinuclear aromatic ring system cont~n~ng 6 to 14 carbon ring members, eg. phenyl, naphthyl and anthracenyl;
~ 2~99'12~
aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen: aryl as stated above or mononuclear or dinuclear heteroaryl, eg.
- S-membered hetaryl con~in~ng one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom:
hetaryl which has a S-membered ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg. 2-furyl, 3-~uryl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, ( 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
- benzofused 5-membered hetaryl cont~joi~g one to three nitrogen atoms or one nitrogen atom and one oxyqen or sulfur atoms hetaryl which has a 5 ~~h~red ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two neighboring carbon ring members or one nitrogen and one neighboring carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group;
30 - 5-membered hetaryl bonded via nitroqen and çon~in;~g one to four nitrogen atoms or benzofused 5-membered hetaryl bonded via nitrogen and conta~n~g one to three nitrogen atoms:
hetaryl which has a 5-membered ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two neighboring carbon ring members or one nitrogen and one neighboring carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one o~ the nitrogen ring members;
- 6-membered hetaryl con~in~ng one to three ox one to four nitroqen atoms: hetaryl which has a 6-membered ring and, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, ~U~ V4 ~ 31 219~122 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;
alkylene: divalent straight chains of 3 to 5 CH2 yr O~S~ eg.
5 -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- and -CH2CH2CH2CH2CH2-;
oxyalkylene: divalent straight ch~ns of 2 to 4 CH2 groups, one valency being bonded to the skeleton via an oxygen atom, eg.
-OCH2CH2-, -OCH2CH2CH2- and -OCH2CH2CH2CH2-;
oxyalkyleneoxys divalent straight ch~nc of 1 to 3 CH2 y~U~S~
both valencies being bonded to the skeleton via an oxygen atom, eg. -OCH20-, -OCH2CH20- and -OCH2CH2CH20-;
15 alkenylene: divalent straight ch~; n.c comprising 1 to 3 CH2 groups and one CH=CH group in any desired position, eg. -CH=CHCH2-, --CH2CH=CHCH2--,-CH=CHCH2CH2--, -CH2CH=CHCH2CH2- and -CH=CHCH2CH2CH2-;
20 oxyalkenylene: divalent straight chains comprising O to 2 CH2 yLO~ and one CH=CH group in any desired position, one valency being bonded to the skeleton via an oxygen atom, eg. -OCH=CH-, --OCH=CHCH2--,-OCH2CH=CH--, --OCH2CH=CHCH2--, -OCH=CHCH2CH2- and -OCH2CH2-CH=CH-;
oxyalkenyleneoxy: divalent straight chains comprising O to 2 CH2 yLO~S and one CH=CH group in any desired position, both valen~ies being bonded to the skeleton via an oxygen atom, eg.
-OCH=CHO-, -OCH=CHCH20-, -OCH2CH=CHCH20- and -OCH=CHCH2CH20-;
f organic radical: substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl.
The additional term "unsubstitued or substituted" in relation to 35 alkyl, alkenyl and alkynyl groups is intended to express the fact that these groups may be partially or completely halogenated (ie.
some or all of the hydrogen atoms of these groups may be replaced by identical or different halogen atoms as stated above ~preferably fluorine, chlorine or bromine) and/or may carry one 40 to three (preferably one) of the following radicals:
cyano, nitro, hydroxyl, amino, formyl, carboxyl, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, 45 alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, where the alkyl groups in these radicals preferably contain 1 to 6, in partiuclar 1 to 4, carbon atoms;
cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, 5 cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, which i~ unsubstituted or substituted by conventional groups, where the cyclic systems contain 3 to 12, preferably 2 to 8, in particular 3 to 6, ring members and the alkyl ~ oups in these 10 radicals contain preferably l to 6, in partiuclar 1 to 4, carbon atoms;
aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, 15 arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, f hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamlno or hetarylalkyl-N-alkylamino, which is unsubstituted or substituted by conventional groups, where the aryl radicals contain preferably 6 to 10, in particular 20 6, ring members (phenyl), the hetaryl radicals contain in particular 5 or 6 ring members and the alkyl groups in these radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms.
25 The additional term "unsubstituted or substituted" in relation to the cyclic fsaturated, unsaturated or aromatic) groups is intended to express the fact that these groups may be partially or co~pletely halogenated (ie. some or all of the hydrogen atoms of these groups may be replaced by identical or different halogen 30 atoms as stated above (preferably fluorine, chlorine or bromine, f in particular fluorine or chlorine) and/or may carry one to four (in particular one to three) of the following radicals:
cyano, nitro, hydroxyl, amino, carboxyl, aminocarbonyl, alkyl, 35 haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, 40 alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, where the alkyl groups in these radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms and the stated alkenyl or alkynyl groups in these radicals contain 2 to 8, preferably 2 to 6, in particular 2 to 4, carbon 45 atoms;
0~50/4g204 2199~22 and/or one to three (in particular one) of the following radicals:
cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, 5 cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, which is unsubstituted or substituted by conventional groups, where the cyclic systems contain 3 to 12, preferably 2 to 8, in particular 3 to 6, ring members and the alkyl groups in these 10 radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms;
aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, 15 arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, f hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino or hetarylalkyl-N-alkylamino, which is unsubstituted or substituted by conventional yLG~S, the aryl radicals cont~n~ng preferably 6 to 10, in particular 6, 20 ring members (phenyl), the hetaryl radicals cont~;n~ng in particular 5 or 6 ring members and the alkyl groups in these radicals cont~n;ng preferably 1 to 6, in particular 1 to 4, carbon atoms, 25 and/or one or two (in particular one) of the following radicals:
formyl or CRiii=NORiV, where Riii is hydrogen or alkyl and RiV is alkyl or arylalkyl and the stated alkyl y~OUpS contain preferably 1 to 6, in particular 1 to 4, carbon atoms and aryl is in 30 particular phenyl which is unsubstituted or which may be f . substituted by conventional groups, or in which two neighboring carbon atoms of the cyclic systems may carry a C3-C5-alkylene, C3-C5--alkenylene,oxy-C2-C4--alkylene,oxy-Cl--C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy- or butadienediyl 35 group, where these bridges in turn may be partially or co~pletely halogenated and/or may carry one to three, in particular one or two of the following radicals: Cl-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy and Cl-C4-alkylthio.
40 Conventional groups are to be understood as meaning in particular the following substituents: halogen, cyano, nitro, C1-C4-alkyl, Cl-C4--haloalkyl,Cl-C4--alkoxy,Cl-C4--halo~oYy, Cl-C4--alkylamino, di-Cl-C4-alkylamino and Cl-C4-alkylthio.
0050/45204 2 1 ~ 9 ~ 2 2 With regard to their use as intermediates in the preparation of compounds I, particularly preferred compounds are those of the formula XX
Xn~ R ( XX ) where Ri is CHO, CH(OH)CN, CH(O~)CO2R", CH(Hal)CO2R" or.
CH(~al)-CO-Hal, R" is C1-C4-alkyl, f X ic cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, ~ Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n i8 ~ 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy--C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these ch~ns in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-4--haloalkyl,Cl-C4--alkoxy, Cl-4-haloalkoxy or Cl-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, and 30 R is halogen, hydroxyl, mercapto, amino, carboxyl, f carbonylamino or - . an organic radical which is bonded directly or ~ia an oxy, mercapto, amino, carboxyl or carbonylamino group, or, together with a group X and the phenyl ring to which they are bonded, may form an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
With regard to their use as intermediates in the preparation of the compounds I, other particularly preferred c~ ~u.lds are those 45 of the formula XXI
~ 2199422 Xn ~ RRiv~ (XXI) 5 where R~i is CHO, CH(OH)CN, CH(OH)CO2R", CH(Hal)CO2R" or CH(OR')CO2R" and CH(Hal)-COHal, 10 R' and R"are each Cl-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is ~ 1, a C3-Cs-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4 - haloalkoxy or Cl-C4 - alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, Rv is halogen, hydroxyl, mercapto, amino, carboxyl, Cl-C4-alkoxycarbonyl, carbonylamino, CRaO, CHRa-Hal, CHR~-Hal, CHRf-Hal, CH2-ORa or CHRa-e, 30 Hal .is halogen, Ra is hydrogen, alkyl, haloalkyl or unsubstituted or substituted aryl, 35 R~ and Rf are each hydrogen, alkyl or cycloalkyl, Ra is hydrogen, alkyl, alkylcarbonyl or unsubstituted or substituted aryl, 40 e i5 a group P03+Hal~ or a group P(=O)(ORX)2, 0 is unsubstituted or substituted aryl, and Rx is alkyl or unsubstituted or su~stituted aryl.
~ 2199422 With regard to their biological actlvity, particularly preferred compounds are those of the formula I.A
CH(UR~ )COVR~ r Xn~ I . A
ya Aa where R' and R"are each C1-C4-alkyl, X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or, f where n is > 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl--C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or C1-C4-alkylthio;
25 n i5 0~ 1~ 2 or 3, and the radicals X may be different when n is > 1, ya is oxymethylene, methyleneoxy, ethylene or ethenylene and Aa i8 aryl or hetaryl which may be substituted by conventional groups and/or may carry one or two (in particular one) of the following radicals: formyl or CRiii=NoRiv o Particularly preferred compounds I.A are those in which ya is methyleneoxy.
Compounds I.A in which ya is oxymethylene are also particularly 40 preferred.
Other particularly preferred compounds I.A are those in which Y~
is ethenylene.
45 Compounds I.A in which ya is ethylene are furthermore particularly preferred.
~ 2199~2 Particularly preferred co..~ounds I.A are those in which Aa i8 unsubstituted or substituted aryl.
Compounds I.A in which Aa is an unsubstituted or substituted 5 6-membered hetaryl ring are also particularly preferred.
Other particularly preferred ~o,..~ounds I.A are those in which Aa is an unsubstituted or substituted 5-membered hetaryl ring.
10 Compounds I.A in which Aa is unsubstituted or substituted aryl which carries a group CRiiisNORiV are furthermore particularly preferred.
Compounds I.A in which Aa is unsubstituted or substituted phenyl 15 which carries a group CRii=O are furthermore particularly ( preferred.
Compounds I.A in which Aa is unsubstituted or substituted phenyl which carries a group CRiii=NORi~ are also particularly preferred.
Other particularly preferred compounds I.A are those in which Aa is unsubstituted or substituted pyridyl or pyrimidyl.
Compounds of the formula I.B
~ " CH(UR')COVR'' Xn~ yb _Ab I.B
30 where R' and Rnare each C1-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-4-alkylthio or, where n is ~ 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3--alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl--4--alkoxy, C1-C4-haloalkoxy or Cl-C4-alkylthio;
45 n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, 38 2199~22 yb iS oxygen, sulfur, amino or alkylamino and Ab is aryl or hetaryl which may be substituted by conventional groups and/or may carry one or two (in particular one) of the following radicals: formyl, CRiii=NORiV or hetaryl (in particular pyridyl, pyrimidyl or triazynyl) or aryl (in particular phenyl) which i8 unsubstituted or substsituted by conventional yLOu~s-10 Particularly preferred compounds I.B are those in wich yb iS
oxygen.
Compounds I.B in which yb iS sulfur are also particularly preferred.
Compounds I.B in which Ab i5 unsubstituted or substituted aryl are furthermore particularly preferred.
Compounds I.B in which Ab is an unsubstituted or substituted 20 6-membered hetaryl ring are also particularly preferred.
Other particularly preferred compounds I.B are those in which Ab is an unsubstituted or substituted aryl or hetaryl ring selected from the group consisting of phenyl, pyridyl, pyrimidyl, 25 pyrazynyl and 1,3,5-triazynyl.
Co..,pounds I.B in which Ab is unsubstituted or substituted 4-pyridyl which carries an unsubstituted or substituted phenoxy radical in the 6 position are also particularly preferred.
Co...~ou~lds I.B in which Ab is unsubstituted or substituted pyrimidinyl which carries an unsubstituted or substituted pyridyloxy radical are furthermore particularly preferred.
35 Compounds I.B in which Ab is unsubstituted or substituted 1,3,5-triazynyl which carries an unsubstituted or substituted phenoxy radical in the 4 position are also particularly preferred.
40 Compounds of the formula I.C
~" CH(UR')COVR'' Xn ~ yc_Ac I.C
where 0050/gs204 ~ 2199~22 R' and R"are each C1-C4-alkyl, X 1s cyano, nitro, halogen, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, f yc is CRY R~-C(=O)-Wc-ic a single or double bond and, in the case of a single bond, the relevant carbon atoms each furthermore carry a hydrogen atom, RY i8 hydrogen or alkyl, 25 R~ i8 hydrogen, cyano, nitro, halogen or alkyl, W is oxygen, sulfur, amino or alkylamino, c is O or 1, f -~ is a bond to Ac and Ac is alkyl, alkenyl, alkynyl or cycloalkyl or is aryl, arylalkyl, arylalkenyl, hetaryl, hetarylalkyl or hetarylalkenyl which is unsubstituted or substituted by conventional groups.
Particularly preferred compounds I.C are those in which yc is CH=C(halogen)-C(=O)-O-~-CGh,~o~nds I.C in which yc i3 CH=C(halogen)-C(=O)-NH-~ are also particularly preferred.
Other particularly preferred cGr-~o~nds I.C are those in which yc 45 is CH=C(halogen)-C(=O)-NH-~-005U/4~:!04 -2199~22 Compounds I.C in which yc is CH=C(halogen)-C(=O)-~ are also particularly preferred.
C~ ounds I.C in which Ac i5 alkyl are furthermore particularl 5 preferred.
Co~ nds I.C in which Ac is alkenyl are also particularly preferred.
10 Other particularly preferred cv,..pGui.ds I.C are those in which Ac is alkynyl.
Compounds of the formula I.D
Xn ~ CH(UR')COVR'' I.D
CH20 C~Ad wherein R' and R"are each Cl-C4-alkyl, X i8 cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is ~ 1 , a C~-Cs-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atom~ of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, ~r . 'Cl-C4--alkyl~Cl-C4--haloalkyl~Cl-C4--alkoxy, ~ Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n i8 ~ I ~ and Ad i8 cycloalkyl which may carry one to four of the following substituents: cyano, halogen, alkyl, haloalkyl or alkoxycarbonyl, or aryl, arylalkyl or arylalkenyl which is unsubstituted or substituted by conventional yLOups ~
are furthermore preferred.
45 Particularly preferred compounds I.D are those in which Ad is unsubstituted or substituted cyclopropyl.
Compounds of the formula I.E
~ " CH(UR')COVR'' Xn ~ I.E
~i ye_Ae where R' and R"are each C1-C4-alkyl, X i8 cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1 , a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl--C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or f butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X ~ay be different when n is > 1, and 25 YQ i s CRa=N--z a_~
Ra is hydrogen, alkyl or haloalkyl or is aryl which is unsubstituted or substituted by conventional groups, 30 za is oxygen, amino or alkylamino, f -# is a bond to Ae and Ae is hydrogen, unsubstituted or substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynylcarbonyl or alkynyloxycarbonyl, unsubstituted or substituted cycloalkyl, heterocyclyl, aryl, arylalkyl, axyloxyalkyl, arylalkenyl, aryloxyalkenyl, arylcarbonyl, aryloxycarbonyl, hetaryl, hetarylalkyl, hetaryloxyalkyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylcarbonyl or hetaryloxycarbonyl, 2I99~22 are furthermore preferred.
Particularly preferred compounds I.E are those in which ye is CH2N-O-~.
C- _~nds I.E in which ye is CH=N-NH-# are also particularly preferred.
other particularly preferred cv~ nds I.E are those in which ye 10 is CH=N-N(CH3)-~.
Compounds I.E in which Ae is alkyl are furthermore particularly preferred.
15 C- E-unds I.E in which AQ is unsubstituted or substituted ( arylalkyl are also particularly preferred.
other particularly preferred ~ vunds I.E are those in which Ae is unsubstituted or substituted hetarylalkyl.
Compounds of the formula I.F
~" CH(UR')COVR'' X~ ~ I.F
CH20-Af where R' and R"are each C1-C4-alkyl, f X is cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy~ C1-C4-alkylthio or, where n is ~ 1, a C3-Cs - alkylene, C3-C5-alkenylene, oxy--C2-C4-alkylene, oxy--Cl-C3--alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-4--alkyl,Cl--C4--haloalkyl,Cl-C4--alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, 0050~45204 2 1 ~ 9 4 2 2 Af is a phthalimido group which is unsubstituted or substituted by conventional group~ or is a radical --N=CRgRh, 5 Rg is hydrogen, halogen, cyano, nitro, unsu~stituted or substituted alkyl, alkenyl or alkynyl or unsubstituted or substituted cycloalkyl, heterocyclyl, aryl or heteroaryl, Rh i8 hydrogen, unsubstituted or substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl and alkynyloxycarbonyl, unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, arylalkenyl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy or ~0 Rg and Rh~ together with the carbon atom to which they are bonded, form cycloalkyl, cycloalkenyl or saturated or partially unsaturated heterocyclyl which i~ unsubstituted or substituted by conventional groups.
35 Compounds I.F in which Rq is alkyl are furthermore particularly preferred.
Other particularly preferred compounds I.F are the those in which Rg is cycloalkyl.
Compounds I.F in which Rq is haloalkyl are also particularly preferred.
Compounds I.F in which Rg is cyano are furthermore particularly 45 preferred.
2199~22 C~r.~po~nds I.F in which Rg is alkylthio are also particularly preferred.
Compounds I.F in which Rg is methyl, ethyl, n-propyl, CYC1O~LO~Y1r 5 trifluoromethyl, cyano or methylthio are also particularly preferred.
Col..~ounds I.F in which Rh is unsubstituted or substituted aryl are furthermore particularly pre~erred.
Compounds I.F in which Rh is unsubstituted or substituted hetaryl are also particularly preferred.
Other particularly preferred co.l.pG~Ilds I.F are those in which Rh f~ 15 is alkyl.
Compounds I.F in which Rh is cyaloalkyl are also particularly preferred.
20 Compounds I.F in which Rh is unsubstituted or substituted phenyl or pyridyl are furthermore particularly preferred.
Compounds of the formula I.G
CH(UR' )COVR' ' Xn ~ I.G
Yg Ag where R' and R" are each C1-C4-alkyl, X is cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, Y9 is oxygen, sulfur or NRk, Rk is hydrogen, unsubstituted or substituted alkyl, alkenyl or alkynyl or unsubstituted or substituted cycloalkyl, heterocyclyl, aryl or hetaryl, Ag is hydrogen, unsubstituted or substituted alkyl, alkoxy, ( alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl or alkynyloxycarbonyl or unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, aryl~lke~yl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, ~5 aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy, f are furthermore preferred.
Particularly preferred compounds I.G are those in which Y9 is 35 oxygen.
Compounds I.G in which Ag is unsubstituted or substituted aryl are also particularly preferred.
40 Other part~cularly preferred compounds I.G are those in which Ag is unsubstituted or substituted phenyl.
Other particularly preferred c~i"~ou~ds I.G are those in which Ag is unsubstituted or substituted hetaryl.
2I99 1~2 Compounds I.G in which Ag is unsubstituted or substituted alkyl, alkenyl or alkynyl are also particularly preferred.
Co...~u~lds I.G in which Ag is unsubstituted or substituted 5 triazolyl are furthermore particularly preferred.
Co...~ounds of the formula I.H
CH(UR')COVR'' Xn~ I.H
~J~
xhm Ah 15 where R' and R"are each C1-C4-alkyl, X and xh are each cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or, where n is ~ 1, a C3 - C5 - alkylene, C3-Cs--alkenylene,oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2--C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chA;~s in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio;
f n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, m is 0, 1 or 2, and the radicals Xh may be different when m is ~ 1, and Ah is hydrogen, cyano, nitro, halogen, unsubstituted or substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenylQxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl or alkynyloxycarbonyl or unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, arylalkenyl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy, are furthermore preferred.
Particularly preferred c~ oul,ds I.H are those in which Xh is hydrogen.
Co".~o~nds I.H in which Ah is unsubstituted or substituted aryl are 15 also particularly preferred.
Compounds I.H in which Ah is unsubstituted or substituted hetaryl are furthermore particularly preferred.
20 Other particularly preferred c~ oullds I.H are those in which Ah is substituted alkyl.
Compounds l.H in which Ah is substituted alkenyl are also particularly preferred.
Compounds l.H in which Ah is substituted alkynyl are furthermore particularly preferred.
Compounds I.H in which Ah is phenyl substituted by conventional 30 groups are also particularly preferred.
f Co.,.~o~l.ds of the formula I.K
CH(UR')COVR'' Xn ~ yk_Ak I.K
where 40 R' and R are each Cl-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon , .
21991~2 atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals, halogen, Cl-C4--alkyl,Cl-4--haloalkyl,Cl-C4--alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, yk is C~lRf--ON=CRe--CRd=NO--#, Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted aryl;
15 Rf is hydrogen, alkyl or cycloalkyl;
~f -# i8 a bond to A~, Ak is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C3-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, where these groups may be partially or completely halogenated or may carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, Cl-C6--alkylsulfonyl,Cl-C6--alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6--alkoxy,Cl-C6--haloalkoxy, C1-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, Cl-C6-alkylamino, Cl-C6-alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl--C6-alkylaminothiocarbonyl, C2-C6--alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or hetarylthio, where the aromatic and hetero aromatic radicals in turn may be partially or completely halogenated and~or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6--alkylsulfonyl,Cl--C6--alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6--alkoxy,Cl-C6--haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl--C6--alkylamino,Cl--C6--alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, ~ 2199~22 C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(--NORl)--Zo-R2~
aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, where these groups may be partially or completely halogenated or may carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6--alkylcarbonyl,Cl-C6--alkylsulfonyl, Cl-C6--alkylsulfoxyl,C3-C6-cycloalkyl, Cl-C6--alkoxy, Cl-C6--haloalkoxy,Cl-C6--alkoxycarbonyl,Cl--C6--alkylthio, Cl-C6--alkylamino,di-Cl-C6-alkylamino, Cl-C6--alkylaminocarbonyl,di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6--alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NORl)-Zo~R
Z i8 oxygen, sulfur or nitrogen, and the nitrogen carries hydrogen or Cl-C6-alkyl, O i8 0 or 1, Rl is hydrogen or Cl-C6-alkyl and R2 i9 hydrogen or Cl-C6-alkyl, are furthermore preferred.
Particularly preferred co.,lpound~ I.K are those in which yk i~
CH2-ON=C ( CH3 ) -C ( alkyl)sN-O-#.
35 Compounds I.K in which yk is CH2-ON=C(CH3)-C(aryl)=NO-~ are also particularly preferred.
Other particularly preferred co.,.~ounds I.K are those in which Y~
i s CH2-ONsC ( CH3 ) -C ( cycloalkyl)=NO-*.
Compounds I.K in which yk is CH2-ON=C ( CH3 ) -C ( hetaryl)=NO-# are also particularly preferred.
Compounds I.K in which yk is CH2-ONsC ( CH3 ) -C ( CH3 ) =NO-# are 45 furthermore particularly preferred.
_ 0050/4520~
so Compounds I.K in which yk is CH2-ON=C ( CH3 ) -C (C6Hs)=NO-~ are also particularly preferred.
Other particularly preferred compounds I.K are those in which Ak 5 is hydrogen or C1-C6-alkyl.
Compounds I.K in which Ak is unsubstituted or substituted arylalkyl, hetarylalkyl, aryloxyalkyl or hetaryloxyalkyl are also particularly preferred.
Compounds I.K in which Ak is unsubstituted or substituted aryl or hetaryl are furthermore particularly preferred.
Compounds I.K in which Ak is methyl or ethyl are also particularly 15 preferred.
other particularly preferred compounds I.K are those in which Ak is unsubstituted or substituted arylalkyl or heteroarylalkyl.
20 Particularly preferred compounds I (or I.A to I.K) are those in which U is oxygen and V is nitrogen or amino.
CG,I-~o~lds I (or I.A to I.K) in which U is amino and V is oxygen are also particularly preferred.
Co~.poul~ds I (or I.A to I.R) in which U i8 aminooxy and V is oxygen are furthermore particularly preferred.
Particularly preferred cvl.,~ou~lds I (or I.A to I.K) are those in 30 which R' is methyl or ethyl, in particular methyl.
other particularly preferred compounds I (or I.A to I.K) are those in which R" is methyl or ethyl, in particular methyl.
35 Further particularly preferred compounds I (or I.A to I.~) are those in which n is O or 1, in particular 0.
With respect to the CH(UR')-COVRn group, the compounds I may be present in the R or S configuration.
, COVR"H
Xn~ J~COVR Xn~ ~UR' (R) (S) U~/4~
~ 51 2199~22 Accordingly, racemates or, where the radical R can assume different spatial forms, isomer mixtures are generally formed in the preparation. These racemates or isomer mixtures can be resolved in to the initial isomers in a -nner known per se.
5 With regard to their biological activity, both the racemates or isomer mixtures and the pure isomers may be used, the pure isomers having a better effect than the racemates or isomer mixtures.
10 With regard to their use, the compounds I listed in the tables below are particularly preferred. Moreover, the groups stated in the tables for a substituent are by themselves (independently of the combination in which they are mentioned) a particularly preferred embo~i -nt of the relevant substituent.
~ 2~9122 Table 1 Compounds of the general formula I.A (n = 0) in which UR' is 5 methoxy, VR" iB methoxy, ya is -CH20-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 2 10 Compounds of the general formula I.A (n = 0) in which UR' i5 ethoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# s bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 3 . 15 ! Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is ethoxy, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
20 Table 4 C~.,.~ounds of the general formula I.A (n = 0) in which UR' is ethoxy, VR" i8 ethoxy, ya i8 -CH2o-$ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 5 Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is methoxy, ya iS -CH2S-~ = bond to Aa) and A~
30 corresponds to one of the groups stated in Table A
f Table 6 Compounds of the general formula I.A (n z 0), in which UR' is 35 ethoxy, VR" is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 7 40 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH=CH- and Aa corresponds to one of the groups stated in Table A
:
005~/45204 2 1 9 ~
Table 8 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH=CH- and Aa corresponds to one of 5 the groups stated in Table A
Table 9 Compounds of the general formula I.A (n = 0), in which UR' is 10 methoxy, VR~' is methoxy, ya is -OCH2-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 10 15 Compounds of the general formula I.A (n = 0), in which UR' is ( ethoxy, VR" is methoxy, ya is -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 11 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
25 Table 12 Co~ G~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i~ -cH2o-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
f Table 13 Col,.poul.ds of the general formula I.A (n = 0), in which UR' i~
methoxy, VR is ethylamino, ya is -CH2o-$ (-# = bond to Aa) and Aa 35 corresponds to one of the groups stated in Table A
Table 14 Compounds of the general formula I.A (n = 0), in which UR' is 40 ethoxy, VR" is ethylamino, ya is -CH20-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 15 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH25-~ (-# = bond to Aa) and 5 Aa corresponds to one of the groups stated in Table A
Table 16 Compounds of the general formula I.A (n = 0), in which UR' is 10 ethoxy, VR" is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa corresponds to one o~ the groups stated in Table A
Table 17 15 Compounds of the general formula I.A (n = 0), in which UR~ is f methoxy, VR~' is methylamino, ya iS -CH=CH- and Aa corresponds to one of the groups stated in Table A
Table 18 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH=CH- and Aa corresponds to one of the groups stated in Table A
25 Table 19 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
r Table 20 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methylamino, ya is -OCH2-# (-~ = bond to Aa) and Aa 35 corresponds to one of the groups stated in Table A
Table 21 Compounds of the general formula I.A (n = 0), in which UR' is 40 methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
0050/45204 ~ I 9 3 1 ~ 2 2199~2 Table 22 Compounds of the general formula I.A (n = 0), in which UR~ is ethylamino, VR" is methoxy, ya iS -CHzO-# (-# = bond to Aa) and A8 5 corresponds to one of the groups stated in Table A
Table 23 Compounds of the general formula I.A (n = 0), in which UR' is 10 methylamino, VR" is ethoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 24 15 cG",~ou.lds of the general formula I.A (n = 0), in which UR' is ! ethylamino, VR" is ethoxy, ya iS -CH20-# ( - ~ a bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 25 Compounds of the general formula I.A (n z 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH2S-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
25 Table 26 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR~' is methoxy, ya i8 -CH2S-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
f Table 27 Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VRn is methoxy, ya is -CH-CH- and Aa corresponds to 35 one of the groups stated in Table A
Table 28 Compounds of the general formula I.A (n s 0), in which UR' is 40 ethylamino, VR" is methoxy, ya iS -CHzCH- and Aa corresponds to one of the groups stated in Table A
0050/45204 2 1 g ~ 1 22 Table 29 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i8 methoxy, ya is -oCH2-# (-# - bond to Aa) and 5 Aa corresponds to one of the groups stated in Table A
Table 30 Co~pounds of the general formula I.A (n = 0), in which UR' is 10 ethylamino, VR" is methoxy, ya is -OCH2-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
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"~ o~ o ~ ~ ~ d~ Ln ~ r-- ~I ~ o ~ r Ln No. Aa No. Aa No. Aa 36 2,4,6-Trimethylphenyl 271 2-Methyl-5-chlorophenyl 3g7 2-Phenylphenyl o 37 3,4,5-Trimethylphenyl 272 2-Methyl-6-chlorophenyl 398 3-Phenylphenyl ~
38 3-n-Propylphenyl 273 2-Methyl-4-fluorophenyl 399 4-Phenylphenyl o 39 4-n-Propylphenyl 274 2-Methyl-3-bromophenyl 400 2-Phenoxyphenyl 2-iso-Propylphenyl 275 2-Methyl-4-methoxyphenyl 401 4-Phenoxyphenyl 41 3-iso-Propylphenyl 276 2-Methyl-5-methoxyphenyl 402 l-Naphthyl 42 4-iso-Propylphenyl 277 2-Methyl-6-methoxyphenyl 403 2-Naphthyl 43 2,3-Di-isopropylphenyl 278 2-Methyl-4-isopropoxyphenyl 404 9-Anthryl 44 3,5-Di-isopropylphenyl 279 2-Methyl-2,5-dLmethoxyphenyl 405 2-Fluoro-4-ph~noYyphenyl 4-n-Butylphenyl 280 2-Methoxyphenyl 406 3-Fluoro-4-phpnoyyphen 46 4-sec-Butylphenyl 281 3-Methoxyphenyl 407 4-Fluoro-4-rh~noyyphen 47 4-iso-Butylphenyl 282 4-Methoxyphenyl 408 2-Chloro-4-phPnoyyphenyl 48 2-Methyl-4-tert-butylphenyl 283 2-Chloro-5-methylphenyl 409 4-Chloro-4-phenoxyphenyl 49 2-Methyl-6-tert-butylphenyl 284 2-Chloro-4-isopLopylphenyl 410 2-Bromo-4-phenoxyphenyl 2-Methyl-4-isopropylphenyl 285 3-n-P~o~o~y~henyl 411 3-Bromo-4-phenoxyphenyl 51 2-Methyl-4-cyclohexylphenyl 286 3-n-Butoxyphenyl 412 4-Bromo-4-~hPn~yphenyl 52 2-Methyl-4-phenylphenyl 287 3-iso-Butoxyphenyl 413 3-Methyl-1 phenoxyphenyl 53 2-Methyl-4-~enzylphenyl 288 3-n-Pentoxyphenyl 414 4-Methyl-4-phenoxyphenyl 54 3-tert-Butyl-4-phenoxy- 289 4-(Imidazol-l'-yl)phenyl 415 2,5-Dimethylphenyl phenyl ~ 55 2-Methoxy-4-phenoxyphenyl 290 4-(Piperazin-l'-yl)phenyl 416 2-Methyl-4-iodophenyl C~
~3 No. Aa No~ Aa No. Aa O
56 3-Methoxy-4-phenoxyphenyl 291 4-(Morphol; n-l ' - yl)phenyl 417 2-Methyl-5-iodophenyl O
57 4-Methoxy-4-phenoxyphenyl 292 4-(Piperidin-l'-yl)phenyl 418 2,5-Dimethyl-4-iodophenyl 58 3-5-Dichloro-4-phenoxyphenyl 293 4-(Pyridyl-2'-oxy)phenyl 419 2-Me-5-isopropylphenyl o 59 3-4-Dichloro-4-phenoxyphenyl 294 2-Cyclopropylphenyl 420 6-Ethyl-2-pyridyl 4-Ethyl-4-phenoxyphenyl 295 3-Cyclopropylphenyl 421 6-n-Propyl-2-pyridyl 61 4-iso-Propyl-4-phenoxyphenyl 296 3-Cyclohexylphenyl 422 6-iso-Propyl-2-pyridyl 62 2,4-Dimethoxyphenyl 297 4-Cyclohexylphenyl 423 6-n-Butyl-2-pyridyl 63 2,5-Dimethoxyphenyl 298 4-Oxiranylphenyl 424 6-tert-3utyl-2-pyridyl 64 3,6-Dimethoxyphenyl 299 4-(Pyrid-2-yl)phenyl 425 6-n-Phenyl-2-pyridyl 2,3,4-Trimethoxyphenyl 300 3-(Pyrid-2-yl)phenyl 426 6-n-Hexyl-2-pyridyl 66 2-Ethoxyphenyl 301 4-(Pyrid-3-yl)phenyl 427 6-Phenyl-2-pyridyl 67 2-iso-PLopo~y~henyl 302 3-(Pyrid-3-yl)phenyl 428 6-Benzyl-2-pyridyl 68 2-Methyl-3-isopropylphenyl 303 3-(Pyrimid-2-yl)phenyl 429 6-Trifluoromethyl-2-pyridyl 69 2-Methyl-5-isopropylphenyl 304 3-Phenoxyphenyl 430 6-Methoxy-2-pyridyl 2-Benzyloxyphenyl 305 2-Fluoro-3-pheno~yphenyl 431 6-Chloro-2-pyridyl71 3-Benzyloxyphenyl 306 2-Methyl-3-phenoxyphenyl 432 3,6-DLmethyl-2-pyridyl 72 4-Benzyloxyphenyl 307 6-Methyl-2-pyridyl 433 3,6-Diethyl-2-pyridyl 73 4,6-Dimethyl-2-pyridyl 308 5,6-Dimethyl-2-pyridyl 434 4-Phenyl-6-methyl-2-pyridyl 74 4,6-Diphenyl-2-pyridyl 309 3,4-Dichloro-6-methyl- 435 3,4,5~Trichloro- ~3 pyridyl 6-phenyl-2-pyridyl ~
~.
No. Aa No. Aa No. Aa 4-Trifluoromethyl-6-methyl- 310 3-Acetyl-4,6-dimethyl-2- 436 3-Cyano-6-methyl- O
6-2-pyridyl pyridyl 2-pyridyl 76 3-Cyano-6-ethyl-2-pyridyl 311 3-Cyano-6-n-propyl-2-pyridyl 437 3-cyano-iso-pyropyl-2-pyridyl ~
77 3-Cyano-6-cyclo-propyl- 312 3-Cyano-6-n-butyl-2-pyridyl 438 3-Cyano-6-tert-butyl-2-pyridyl 2-pyridyl 78 3-Cyano-6-cyclo-hexyl- 313 3-Cyano-6-phenyl-2-pyridyl 439 3-Methoxycarbonyl-2-pyridyl 6-iso-propyl-2-pyridyl 79 3-Ethoxycar~onyl-6-iso- 314 3-Cyano-4,6-dimethyl-2- 440 3,5,6-Trichloro-propyl-2-pyridyl pyridyl 2-pyridyl 5-Trifluoromethyl-2-pyridyl 315 3-Chloro-5-trifluoromethyl- 441 6-Cyclopropyl-2-pyridyl 2-pyridyl 81 6-Bromo-2-pyridyl 316 4-Trifluoromethyl-5-chloro- 442 4-tert-butyl-2-pyridyl O
2-pyridyl 82 3,6-Bis(trifluoromethyl)- 317 5-Trifluoromethyl-2-pyridyl 443 3-Fluoro-2-pyridyl 2-pyridyl 83 3-Chloro-2-pyridyl 318 4-Bromo-2-pyridyl 444 5-Methyl-2-pyridyl 84 3-Fluoro-5-trifluoromethyl- 319 3,6-Dichloro-5-trifluoro- 445 6-Chloro-4-cyano-2-pyridyl methyl-2-pyridyl 2-pyridyl 4,6-Difluoro-2-pyridyl 320 3,5-Dichloro-6-fluoro-2- 446 6-Methoxy-3-nitro-- pyridyl 2-pyridyl 86 4-Cyano-6-fluoro-2-pyridyl 321 4-Cyano-3,5,6-trifluoro-2- 447 6-Chloro-5-nitro-pyridyl 2-pyridyl 87 4,6-Dicyano-2-pyridyl 322 5-Trichloromethyl-2-pyridyl 448 5-Cyano-2-pyridyl C~
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O ~ O~ O r~ o o o No. Aa No. Aa No. Aa 103 2,3,5,6-Tetrafluoro- 338 2-Pyrimidinyl 464 4,6-Dimethyl- o 4-pyridyl 2-pyrimidinyl 104 4-Trifluoromethyl- 339 4,5,6-Trimethyl- 465 4-Benzyl-6-methyl- ~
2-pyrimidinyl 2-pyrimidinyl 2-pyrimidinyl ~
105 4-Methyl-6-phenyl- 340 4,6-Dimethyl-5-chloro-2- 466 4-Fluoro-2-pyrimidinyl 2-pyrimidinyl pyrimidinyl 106 5-Methyl-2-pyrimidinyl 341 4,6-Difluoro-2-pyrimidinyl 467 4-Pyrimidinyl 107 2,6-Dimethyl-4-pyrimidinyl 342 2,6-Bis-(trifluoromethyl)- 468 2-Chloromethyl-6-methyl-4-pyrimidinyl 4-pyrimidinyl 108 2-Methyl-6-chloromethyl- 343 2-iso-Propyl-6-methyl-4- 469 2-iso-Propyl-6-chloro-4-pyr;~i~;nyl pyrimidinyl methyl-4-pyrimidinyl 109 2-cyclo- Propyl-6-chloro- 344 2-cyclo-Propyl-6-methyl- 470 2-Methyl-6-methoxymethyl-methyl-4-pyrimidinyl 4-pyrimidinyl 4-pyrimidinyl 110 2-iso-Propyl-6-methoxy- 345 2-Phenyl-4-pyri~;~inyl 471 2,5-Dimethyl-methyl-4-pyrimidinyl 4-pyrimidinyl 111 2-Methylthio-6-trifluoro- 346 2-Methylthio-5-chloro- 472 2-Methylthio-5-n-octyl-methyl-4-pyrimidinyl 6-trifluoromethyl-4- 6-methyl-4-pyrimidinyl pyrimidinyl 112 2-Methyl-6-trifluoromethyl- 347 2-n-Propyl-6-trifluoro- 473 2-iso-Propyl-6-tri~luoro-4-pyrimidinyl methyl-4-pyrimidinyl methyl-4-pyrim;~inyl 113 2-n-Propyl-6-methyl- 348 2-tert-Butyl-6-trifluoro- 474 2-Methyl-5-chloro-4-pyrimidinyl methyl-4-pyr;~;~;nyl 6-trifluoromethyl-4-pyrimidinyl 114 2-n-Propyl-5-chloro-6-tri- 349 2-iso-Propyl-5-chloro- 475 2-tert-Butyl-5-chloro-fluoromethyl-4-pyrimidinyl 6-trifluoromethyl-4- 6-trifluoromethyl-pyrimidinyl 4-pyrimidinyl c~
~ 0050/45204 2199 l22 ,~
I ~ r ~
r~ r; o ~ r' ; r ¦ C~ _ C I ~ C
r r l ~ I r l ~r .r ~rl ~l r- ~r ~ ~ ~ . r ct~
J ~ r ~ ~ ,~ ~ o ~-r~ J ~ -rl rl ~-rl t'~ ~ ~ ~ r~l er ; ' ~O r'l C
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r- b ~ C ~ E~ ~ ~~ b ~~~ O ~ ~4 ~ ~ ~ r ~ ~rl C r~ I ~rl ~ C ~ ~r~ ~ r~
~r h ~ ~ ~' ~r -I ~ rl h ~ al - ) Cl ~ ~rl ~ O ~ û -~ ~r C
~ ~ .t~ ~rl ~ V I C ) r E- IPl ~y ~ ~ C~ .r ~r¦ t~ 1 r-l r.~ r l ~ r~ r~ ~
C ~ r C C
r~ ~rl ~ r~ I ~rl ~rl ~r a~ r~ ~ ~r; r r~
~rl b ~ -rl r I I I
u C ~ ,~
~rl ~ I Jr ~rl r~ ~ N I Ir~~
0 S b ~ ~ ~ I ~ r l ~ -1 4 ;r. ~ r~ r O r~ X 5~1 C C C
~ ~ ~U~ ~1 1 ~rl C ~ ~ ~rl -- rl s O ~ ~ C ~ V b ~ r. tJ
I C ~r ~ ~ I I o C I ~,1 ,r ,~ ~ r co ,~
pf ~ ~ r~ N I ~ I ~ u S I ~r~ rl X rl I O ~I r~ -- 1 rl rl rl ~, ~ r~ b ~ O O ~ r ~ ~
5~ ~r ~ 1 S 5~ C ~1 C ~ C ~ t . . .C
C S~ ~ ~ ~ .r~¦ S r- S~ ~V ~r ~~ a) ., ~D W 4 ~ b ~ 1~1 rS ~ ps~ S' ~, ~ I I I I I I I
~i1~1 ~J N ~ N ~ ~ ~ ~ ~ d ~ ~ N N N N
~ O r I N ~ ~ 1~1 ~D t~ a~ 0~ O ~ N t~7 r~1 ~t O O
~ o ~ o ~~a .,9 ,~
C C3 ;~I CC ~r~l r1r~lr~l I ~ e~ r~ C
7J C ~ ~ C ~ ~'1 ~1 ~r~l I I O ~rl ~r~ ~ rU) ~rl r~r~lr~ X ~r~l C ,1 b .~ ~1 ~,1 , b O O r û h ~ .r~ ' ~ ~ r~ b ~ ~ ~ ~ c: ~ I s O ~ ~ I
rl ~ I ~ ~r~¦~r¦ ~~ ~ J ~tr' ~r ~ r l-I ~ r l~~ '~ Ur i au IJ Jr ~t C ~1 1 ~ 1 ~ tJ~ ~ b ~
J I ~ I I I I I O I :-V~ ~rl ~ ~rlr~ ~ N ~ N~ r~ ~ r~ S rJI
r~ ~ ~ I rcJr~>t ¦ I II r~t I C ~1 ~ 3 r~l oo-~l -- r~ s ~ 1 0 r1 r~ ~-1 ~~ tl) ~ ~ ~ ~ b ~ ~ r~t U~t S ~ j~ r CC ~'1 ~ X C-~l ~ s .: _ C s C~ ~rl ~~ -~ ~ o a~ ., r~ Q ., S S ~1 ) S S ~1~rl al ) ) s IU .~ I r r r ; : ~ ~ 04C~ E~ C ~D c~
~¢N ~ ~ N b ~ ~N U~ ~4 tD ~ ~ N ~ N N N CO
Ur-l ~1 _I
Zr ~ r l _I r l ~I r-~ ~I r ~r-~ r l No, Aa No. Aa No. Aa 129 2-Pyrazinyl 364 6-Chloro-2-pyrazinyl 490 5-Methyl-2-pyrazinyl . o 130 3-Pyridazinyl 365 5-Chloro-3-pyri~z; nyl 491 2-Thienyl ~
131 3-Thienyl 366 4-Chloro-3-thienyl 492 2-Chloro-3-thienyl o 132 5-Chloro-3-thienyl 367 4-Chloro-2-thienyl 493 2-Quinoxalinyl 133 3-Methyl-2-quinox~li nyl 368 7r8-Dimethyl-2-quinn~linyl 494 7,8-~ichloro-2-~uinoxalinyl 134 7-Methyl-2-quinoxalinyl 369 8-Methyl-2-~uinoxalinyl 495 7-Methoxy-2-qn; no~; nyl 13S 3-Phenyl-5-isoxazolyl 370 2-BPn~x~olyl 496 2-Benzothiazolyl 136 1-Phenyl-pyrazol-4-yl 371 2-n-Propyl-6-methyl- 497 2-Cyclopentyl-4-pyrimidinyl 6-trifluoromethyl-4-pyrimidinyl 137 2-Cyclohexyl-6-trifluoro- 372 2-Cyclohexyl-5-chloro- 498 2-n-Propyl-5-chloro-methyl-4-pyrimidinyl 6-methyl-4-pyrimidinyl 6-methyl-4-pyrimidinyl 138 Pyrazol-1-yl 373 4-Chlo.opyLazol-1-yl 499 3,5-~imethylpyrazol-1-yl 139 1,2-~Pn7;soxazol-3-yl 374 1-(4-Chlorophenyl)-pyrazol-4 500 1-(4-Methylphenyl)--yl pyrazol-4-yl 140 1-Phenylpyrazol-4-yl 375 1-Methyl-3-trifluoromethyl- 501 1-(4-Fluorophenyl)-pyrazol-5-yl pyrazol-4-yl 141 5-Phenylisoxazol-3-yl 376 Benzotriazol-1-yl 502 3-Cyano-5-nitro-2-pyridyl c~
2 1 9 ~ 2 Table 31 CG..,~oullds of the general formula I.A (n = 0), in which UR' is 5 methoxy, VR" is methoxy, ya iS -CH20-# (-# ~ bond to Aa) and Aa is phenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
10 Table 32 Compounds of.the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(=O)Riii in the 4 position, Riii 15 for a compound corresponding to one of the groups ~tated in Table B
Table 33 20 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-~ (-# = bond to A~) and Aa is phenyl which carries a radical C(=O)Riii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 34 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i8 -CH20~ = bond to Aa) and Aa is 30 phenyl which carries a radical C(=O)Riii in the 3 position, Riil for a c~ oul.d corresponding to one of the yLOU~ stated in Table B
Table 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 40 stated in Table B
Table 36 Compounds of the general formula I.A (n = 0), in which UR~ is 45 ethoxy, VR" i8 methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 4 00~0/45204 219~22 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 37 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i5 methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 3-methylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table B
Table 38 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa~ and Aa is f 3-methylphenyl which carries a radical C(=O)Riii in the 4 - position, Riii for a compound corresponding to one of the groups stated in Table B
20 Table 39 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carrie~ a radical C(=O)Riii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 40 30 Compounds of the general formula I.A (n = 0), in which UR' is f ethoxy, VR" i8 methoxy, ya iS - CH20-# (~~ 5 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a cG,~ u~d corresponding to one of the yL~U~S
stated in Table B
Table 41 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a cv~.~o~nd corresponding to one of the groups stated in Table B
Table 42 Co~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CHzO-# (~~ = bond to Aa) and Aa is 5 2-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 43 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table 3 Table 44 C~l..poul,ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(zO)Riii in the 4 position, Riii for a ~o~ ou~ld corresponding to one of the groups stated in Table B
25 Table 45 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(=O)Riii in the 4 30 position, Riii for a c~ ound corresponding to one of the groups stated in Table B
Table 46 35 CG...~G~lds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 47 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 2-chloro-5-methylphenyl which carries a radical C(=O)Riii in the 4 68 219942~
position, Riii for a cuh.puund corresponding to one of the yLoups stated in Table B
Table 48 Co.,.~oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloLo 5 -thylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table B
Table 49 Compounds of the general formula I.A (n = 0), in which UR' i8 15 methoxy, VR" is methoxy, ya is -CH20-# ~-~ 8 bond to Aa) and Aa i8 ( i-methylphenyl which carries a radical C(=O)Riii in the 5 position, Riii for a compound corresponding to one of the yLOu~
stated in Table B
20 Table 50 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methoxy, ya i5 -CHzO-# (-~ s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 5 25 position, Riii for a co~pound corresponding to one of the yLv~g stated in Table B
Table 51 30 Compounds of the general formula I.A (n = 0), in which UR' ~s methoxy, VR is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(-O)Riii in the 4 position, Riii for a co,,.pvund corresponding to one of the y~uU~S
stated in Table B
Table 52 Compounds of the general for~ula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 40 2,5-dichlorophenyl which carries a radical C('O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
00~0/45204 21 99ll22 Table ~
No. Riii 10 6 CH3(CH2)4 7 CH3(CH2)s 8 CH2-Cl 9 CH2Br 1 0 CH2CH2Cl 15 11 CH2CH2CH2Cl 12 CH2(CHz)3-C
13 CH2(CH2)4 16 CH2CH2~r 17 CH2CH2CH23r 18 CH2(CH2)3-Br CH2-CH(CH3)2 21 CH2-C(CH3)3 22 CH(CH3)2 30 23 t-~utyl 24 Phenyl f; 2S 2-Pyridyl 26 3-Pyridyl 27 4-Pyridyl 35 28 Cyclopropyl 29 Cyclopentyl Cyclohexyl 40 Table 53 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and A~ is phenyl which carries a radical CHsNORiii in the 4 position, Riii 45 for a cG...~ound corresponding to one of the groups stated in Table C
~ 2I9~2 Table 54 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 5 phenyl which carries a radical CH-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 55 C~ ou.lds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~A..~ou~ld corresponding to one of the groups 15 stated in Table C
Table 56 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" i8 methoxy, ya is -CH20-~ (-# 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a co..~o~lld corresponding to one of the groups stated in Table C
25 Table 57 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH20-# (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH~NORiii in the 4 30 positio~, Riii for a ~ G~nd corresponding to one of the groups f- stated in Table C
Table 58 35 Compounds of the general formula I.A (n = Q), in which UR' is ethoxy, VR" is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical CHsNORiii~in the 4 position, Riii for a col"~ound corresponding to one of the groups stated in Table C
Table 59 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 45 2-chlorophenyl which carries a radical CH=NORiii in the 4 0050~45204 71 2199~22 position, Riii for a-compound corresponding to one of the y stated in Table C
Table 60 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ~LOU~S
A further possibility for the preparation of the ~...pounds I.13 5 is first to react the benzyl halide of the formula I.2 with N-hydroxyphthalimide, to convert the re~ulting product into the corresponding benzylhydroxylamine (I.15) by hydrazinolysis and then to react I.15 with a ketoxime of the formula XVIIa to give I.13.
O
CH(UR')-COVR ~
Xn ~ CHRf-Hal HO-N ~ ~~~~' ~'" O
I.2 ~" CH(UR'~-COVR'' Xn ~ CHRf-oNpht (Pht = Ph~h~ ;de radical) CH(UR')-C0VR'' H2NNH2 Xn~
CHRf{)NH2 ~ CH(UR')-COVR'' ~' OCR~--CRd--N~A4~
XVIIa CHRf-oN=cRe-~cRd=No-A4 I.13 The conversion of the benzyl halide I.2 into the benzylhydroxylamine I.15 is carried out in a manner known per se in an inert organic solvent by the methods described in 40 EP-A 463 488 and EP-A 585 751.
Compounds I in which R is substituted or unsubstituted alkynyl are obtained from the cG.~.~ounds I.15 (R=halogen, in parti~ular bromine) by a Heck reaction with an acetylene derivative [cf.
45 J. Organomet. Chem. 93 (1975), 259] in the presence of a transition metal catalyst [TM], for example a palladium or nickel co.ll~ound, such as diacetylpalladium, palladium dichloride, .
2199q22 tetra(triphenylphosphine)palladium or nickel dichloride, in an inert solvent (eg. dimethylformamide, acetonitrile, tetrahydrofuran or toluene) and in the presence of a base (eg.
potassium carbonate, sodium hydride, diethylamine, triethylamine 5 or pyridine).
~" CH(UR')-COVR"
Xn ~ ~ H--C_C--Rt R
I.15 (R=Hal) ~ase Xn ~ CH(UR')-COVR~
~ere, Rt i8 hydrogen, substituted or unsubstituted alkyl, a ~ 20 substituted or unsubstituted saturated or partially unsaturated cyclic radial which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring which, in addition to carbon ring - h~rs, may 25 contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
Alkyl phenyl acetates of the formula I, where R is a group Al-Yl-in which yl i8 a direct bond, oxygen, sulfur, amino or alkylamino and Al is substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic r~ng system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are particularly preferred.
219!3422 25Alkyl phenylacetates of the formula I where R is CH2OAl in which Al is in particular a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms ~elected from the 5 group consisting of oxygen, sulfur and nitrogen, or in which Al is in particular a substituted or unsubstituted aromatic ring which, in addition to carbon ~ing members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are also preferred.
Other preferred alkyl phenylacetates are those of the formula I
where R is a group A2-ZaN=CRa- in which Ra is hydrogen, alkyl, haloalkyl or substituted or unsubstituted aryl;
za is oxygen, amino or alkylamino;
A2 is hydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring h~rs, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of f oxygen, sulfur and nitrogen.
.
Alkyl phenylacetates of the formula I where R is a group A3-CRb=NocHRc- in which Rb is hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
40 Rc is hydrogen, alkyl or cycloalkyl;
A3 substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected -~ ~l9g~22 from the gr~up consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, are furthermore preferred.
10 Other preferred alkyl phenylacetates are those of the formula I
where R is a group A4-oN=CRd-CRe=No-cHRf- in which Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or substituted or unsubstituted aryl;
Rf is hydrogen, alkyl or cycloalkyl;
A4 substituted or unsubstituted alkyl, alkenyl or alkynyl, or a substituted or unsubstituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or a substituted or unsubstituted aromatic ring system which, in addition to carbon xing members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
f Alkyl phenylacetates of the formula I where R and one of the radicals X, together with the phenyl ring to which they are bonded, for~ a substituted or unsubstituted bicyclic structure 35 selected from the group consisting of benzofuran, benzothiophene, indole, isoindole and naphthalene are also particularly preferred.
.
In the definitions of the symbols stated in the above formulae, 40 collective definitions which are representative generally for the following substituents were used:
halogen: fluorine, chlorine, bromine and iodine;
45 alkyl: unsasturated, straight-chain or branched hydrocarbon radicals of 1 to 10 carbon atoms, eg. C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, l-methyl-propyl, 27 219~422 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, l,1-dimethylpropyl, 1,2-dimethylpropyl, l-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 5 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl;
10 haloalkyl: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above), in which some or all of the hydrogen atoms may be.replaced by halogen atoms as above, eg. Cl- or C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 15 chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, ( l-chloroethyl, 1-bromoethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-tri~luoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-~luoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
alkoxy: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an oxygen atom (-O-);
25 haloalkoxy: straight-chain or branched haloalkyl o~ 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an oxygen atom (-0-);
alkylthio: straight-chain or branched alkyl of 1 to 10 or 1 to 4 30 carbon atoms (as stated above) which is bonded to the skeleton f via a sulfur atom (-S-);
alkylamino: straight-chain or branched alkyl of 1 to 10 carbon atoms (as stated above) which is bonded to the skeleton via an 35 amino group (-NH-) or which is bonded to the skeleton via a group -NYl- or -NZ a_;
alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any 40 desired position, eg. C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-buten~l, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 45 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-2~99 1~2 propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-l-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 5 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-10 butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-15 1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-f butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
20 alkynyl: straight-chain or branched hydrocarbon groups having 2 to lO carbon atoms and a triple bond in any desired position, eg.
C2-C6-alkynyl, such as ethynyl, l-propynyl, 2 ~L o~y,lyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-25 butynyl, 1-methyl-3-butynyl, 2-methyl-3 bu~yl-ylr 3-methyl-1-butynyl, l,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl- 1-pentynyl, 3-methyl-4-pentynyl, 30 4-methyl 1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, f 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
35 cycloalkyl: monocyclic alkyl of 3 to 12 carbon ring members, eg.
C3-C8-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; ~
saturated or partially unsaturated cyclic radical which, in 40 addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen: cycloalkyl of 3 to 12 carbon ring members as stated above or 5 -~hered or 6 s~hered heterocyclyl cont~;n;ng, in addition to carbon ring members, from 1 to 3 nitrogen atoms 45 and/or 1 or oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrroiidynyl, -21~9~22 ~ 29 3-pyrrolidynyl, 3-isoxazolidynyl, 4-isoxazolidynyl, 5-isoxazolidynyl, 3-isothiazolidynyl, 4-isothiazolidynyl, 5-isothiazolidynyl, 3-pyrazolidynyl, 4-pyrazolidynyl, 5-pyrazolidynyl, 2-oxazolidynyl, 4-oxazolidynyl, 5-oxazolidynyl, 5 2-thiazolidynyl, 4-thiazolidynyl, 5-thiazolidynyl, 2-imidazolidynyl, 4-imidazolidynyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 10 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl, 15 3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 20 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydlo~yL~zol-l-yl~ 2~3-dihydLo~yLazol-2-yl~
2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydLo~y t azol-1-yl, 2~ 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihyd~o~y~azol-1-yl~
4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 30 2,3-dihydrooxazol-5-yl, 3,4-dihydroo~azol-2-yl, f 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihyd~oo~azol-4-yl, 2-piperidynyl, 3-piperidynyl, 4-piperidynyl, 1,3-dioxane-5-yl, 35 2-tetrahyd~o~y-anyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazynyl, 4-tetrahydropyridazynyl, 2-tetrahydropyrimidynyl, 4-tetrahydropyrimidynyl, 5-tetrahydropyrimidynyl, 2-tetrahydropyrazynyl, 1,3,5-tetrahydro-triazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl;
aryl: a mononuclear to trinuclear aromatic ring system cont~n~ng 6 to 14 carbon ring members, eg. phenyl, naphthyl and anthracenyl;
~ 2~99'12~
aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen: aryl as stated above or mononuclear or dinuclear heteroaryl, eg.
- S-membered hetaryl con~in~ng one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom:
hetaryl which has a S-membered ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg. 2-furyl, 3-~uryl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, ( 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
- benzofused 5-membered hetaryl cont~joi~g one to three nitrogen atoms or one nitrogen atom and one oxyqen or sulfur atoms hetaryl which has a 5 ~~h~red ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two neighboring carbon ring members or one nitrogen and one neighboring carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group;
30 - 5-membered hetaryl bonded via nitroqen and çon~in;~g one to four nitrogen atoms or benzofused 5-membered hetaryl bonded via nitrogen and conta~n~g one to three nitrogen atoms:
hetaryl which has a 5-membered ring and, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two neighboring carbon ring members or one nitrogen and one neighboring carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one o~ the nitrogen ring members;
- 6-membered hetaryl con~in~ng one to three ox one to four nitroqen atoms: hetaryl which has a 6-membered ring and, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, ~U~ V4 ~ 31 219~122 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;
alkylene: divalent straight chains of 3 to 5 CH2 yr O~S~ eg.
5 -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- and -CH2CH2CH2CH2CH2-;
oxyalkylene: divalent straight ch~ns of 2 to 4 CH2 groups, one valency being bonded to the skeleton via an oxygen atom, eg.
-OCH2CH2-, -OCH2CH2CH2- and -OCH2CH2CH2CH2-;
oxyalkyleneoxys divalent straight ch~nc of 1 to 3 CH2 y~U~S~
both valencies being bonded to the skeleton via an oxygen atom, eg. -OCH20-, -OCH2CH20- and -OCH2CH2CH20-;
15 alkenylene: divalent straight ch~; n.c comprising 1 to 3 CH2 groups and one CH=CH group in any desired position, eg. -CH=CHCH2-, --CH2CH=CHCH2--,-CH=CHCH2CH2--, -CH2CH=CHCH2CH2- and -CH=CHCH2CH2CH2-;
20 oxyalkenylene: divalent straight chains comprising O to 2 CH2 yLO~ and one CH=CH group in any desired position, one valency being bonded to the skeleton via an oxygen atom, eg. -OCH=CH-, --OCH=CHCH2--,-OCH2CH=CH--, --OCH2CH=CHCH2--, -OCH=CHCH2CH2- and -OCH2CH2-CH=CH-;
oxyalkenyleneoxy: divalent straight chains comprising O to 2 CH2 yLO~S and one CH=CH group in any desired position, both valen~ies being bonded to the skeleton via an oxygen atom, eg.
-OCH=CHO-, -OCH=CHCH20-, -OCH2CH=CHCH20- and -OCH=CHCH2CH20-;
f organic radical: substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl.
The additional term "unsubstitued or substituted" in relation to 35 alkyl, alkenyl and alkynyl groups is intended to express the fact that these groups may be partially or completely halogenated (ie.
some or all of the hydrogen atoms of these groups may be replaced by identical or different halogen atoms as stated above ~preferably fluorine, chlorine or bromine) and/or may carry one 40 to three (preferably one) of the following radicals:
cyano, nitro, hydroxyl, amino, formyl, carboxyl, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, 45 alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, where the alkyl groups in these radicals preferably contain 1 to 6, in partiuclar 1 to 4, carbon atoms;
cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, 5 cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, which i~ unsubstituted or substituted by conventional groups, where the cyclic systems contain 3 to 12, preferably 2 to 8, in particular 3 to 6, ring members and the alkyl ~ oups in these 10 radicals contain preferably l to 6, in partiuclar 1 to 4, carbon atoms;
aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, 15 arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, f hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamlno or hetarylalkyl-N-alkylamino, which is unsubstituted or substituted by conventional groups, where the aryl radicals contain preferably 6 to 10, in particular 20 6, ring members (phenyl), the hetaryl radicals contain in particular 5 or 6 ring members and the alkyl groups in these radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms.
25 The additional term "unsubstituted or substituted" in relation to the cyclic fsaturated, unsaturated or aromatic) groups is intended to express the fact that these groups may be partially or co~pletely halogenated (ie. some or all of the hydrogen atoms of these groups may be replaced by identical or different halogen 30 atoms as stated above (preferably fluorine, chlorine or bromine, f in particular fluorine or chlorine) and/or may carry one to four (in particular one to three) of the following radicals:
cyano, nitro, hydroxyl, amino, carboxyl, aminocarbonyl, alkyl, 35 haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, 40 alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, where the alkyl groups in these radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms and the stated alkenyl or alkynyl groups in these radicals contain 2 to 8, preferably 2 to 6, in particular 2 to 4, carbon 45 atoms;
0~50/4g204 2199~22 and/or one to three (in particular one) of the following radicals:
cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, 5 cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, which is unsubstituted or substituted by conventional groups, where the cyclic systems contain 3 to 12, preferably 2 to 8, in particular 3 to 6, ring members and the alkyl groups in these 10 radicals contain preferably 1 to 6, in particular 1 to 4, carbon atoms;
aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, 15 arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, f hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino or hetarylalkyl-N-alkylamino, which is unsubstituted or substituted by conventional yLG~S, the aryl radicals cont~n~ng preferably 6 to 10, in particular 6, 20 ring members (phenyl), the hetaryl radicals cont~;n~ng in particular 5 or 6 ring members and the alkyl groups in these radicals cont~n;ng preferably 1 to 6, in particular 1 to 4, carbon atoms, 25 and/or one or two (in particular one) of the following radicals:
formyl or CRiii=NORiV, where Riii is hydrogen or alkyl and RiV is alkyl or arylalkyl and the stated alkyl y~OUpS contain preferably 1 to 6, in particular 1 to 4, carbon atoms and aryl is in 30 particular phenyl which is unsubstituted or which may be f . substituted by conventional groups, or in which two neighboring carbon atoms of the cyclic systems may carry a C3-C5-alkylene, C3-C5--alkenylene,oxy-C2-C4--alkylene,oxy-Cl--C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy- or butadienediyl 35 group, where these bridges in turn may be partially or co~pletely halogenated and/or may carry one to three, in particular one or two of the following radicals: Cl-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy and Cl-C4-alkylthio.
40 Conventional groups are to be understood as meaning in particular the following substituents: halogen, cyano, nitro, C1-C4-alkyl, Cl-C4--haloalkyl,Cl-C4--alkoxy,Cl-C4--halo~oYy, Cl-C4--alkylamino, di-Cl-C4-alkylamino and Cl-C4-alkylthio.
0050/45204 2 1 ~ 9 ~ 2 2 With regard to their use as intermediates in the preparation of compounds I, particularly preferred compounds are those of the formula XX
Xn~ R ( XX ) where Ri is CHO, CH(OH)CN, CH(O~)CO2R", CH(Hal)CO2R" or.
CH(~al)-CO-Hal, R" is C1-C4-alkyl, f X ic cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, ~ Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n i8 ~ 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy--C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these ch~ns in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-4--haloalkyl,Cl-C4--alkoxy, Cl-4-haloalkoxy or Cl-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, and 30 R is halogen, hydroxyl, mercapto, amino, carboxyl, f carbonylamino or - . an organic radical which is bonded directly or ~ia an oxy, mercapto, amino, carboxyl or carbonylamino group, or, together with a group X and the phenyl ring to which they are bonded, may form an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
With regard to their use as intermediates in the preparation of the compounds I, other particularly preferred c~ ~u.lds are those 45 of the formula XXI
~ 2199422 Xn ~ RRiv~ (XXI) 5 where R~i is CHO, CH(OH)CN, CH(OH)CO2R", CH(Hal)CO2R" or CH(OR')CO2R" and CH(Hal)-COHal, 10 R' and R"are each Cl-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is ~ 1, a C3-Cs-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4 - haloalkoxy or Cl-C4 - alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, Rv is halogen, hydroxyl, mercapto, amino, carboxyl, Cl-C4-alkoxycarbonyl, carbonylamino, CRaO, CHRa-Hal, CHR~-Hal, CHRf-Hal, CH2-ORa or CHRa-e, 30 Hal .is halogen, Ra is hydrogen, alkyl, haloalkyl or unsubstituted or substituted aryl, 35 R~ and Rf are each hydrogen, alkyl or cycloalkyl, Ra is hydrogen, alkyl, alkylcarbonyl or unsubstituted or substituted aryl, 40 e i5 a group P03+Hal~ or a group P(=O)(ORX)2, 0 is unsubstituted or substituted aryl, and Rx is alkyl or unsubstituted or su~stituted aryl.
~ 2199422 With regard to their biological actlvity, particularly preferred compounds are those of the formula I.A
CH(UR~ )COVR~ r Xn~ I . A
ya Aa where R' and R"are each C1-C4-alkyl, X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or, f where n is > 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl--C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or C1-C4-alkylthio;
25 n i5 0~ 1~ 2 or 3, and the radicals X may be different when n is > 1, ya is oxymethylene, methyleneoxy, ethylene or ethenylene and Aa i8 aryl or hetaryl which may be substituted by conventional groups and/or may carry one or two (in particular one) of the following radicals: formyl or CRiii=NoRiv o Particularly preferred compounds I.A are those in which ya is methyleneoxy.
Compounds I.A in which ya is oxymethylene are also particularly 40 preferred.
Other particularly preferred compounds I.A are those in which Y~
is ethenylene.
45 Compounds I.A in which ya is ethylene are furthermore particularly preferred.
~ 2199~2 Particularly preferred co..~ounds I.A are those in which Aa i8 unsubstituted or substituted aryl.
Compounds I.A in which Aa is an unsubstituted or substituted 5 6-membered hetaryl ring are also particularly preferred.
Other particularly preferred ~o,..~ounds I.A are those in which Aa is an unsubstituted or substituted 5-membered hetaryl ring.
10 Compounds I.A in which Aa is unsubstituted or substituted aryl which carries a group CRiiisNORiV are furthermore particularly preferred.
Compounds I.A in which Aa is unsubstituted or substituted phenyl 15 which carries a group CRii=O are furthermore particularly ( preferred.
Compounds I.A in which Aa is unsubstituted or substituted phenyl which carries a group CRiii=NORi~ are also particularly preferred.
Other particularly preferred compounds I.A are those in which Aa is unsubstituted or substituted pyridyl or pyrimidyl.
Compounds of the formula I.B
~ " CH(UR')COVR'' Xn~ yb _Ab I.B
30 where R' and Rnare each C1-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-4-alkylthio or, where n is ~ 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3--alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl--4--alkoxy, C1-C4-haloalkoxy or Cl-C4-alkylthio;
45 n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, 38 2199~22 yb iS oxygen, sulfur, amino or alkylamino and Ab is aryl or hetaryl which may be substituted by conventional groups and/or may carry one or two (in particular one) of the following radicals: formyl, CRiii=NORiV or hetaryl (in particular pyridyl, pyrimidyl or triazynyl) or aryl (in particular phenyl) which i8 unsubstituted or substsituted by conventional yLOu~s-10 Particularly preferred compounds I.B are those in wich yb iS
oxygen.
Compounds I.B in which yb iS sulfur are also particularly preferred.
Compounds I.B in which Ab i5 unsubstituted or substituted aryl are furthermore particularly preferred.
Compounds I.B in which Ab is an unsubstituted or substituted 20 6-membered hetaryl ring are also particularly preferred.
Other particularly preferred compounds I.B are those in which Ab is an unsubstituted or substituted aryl or hetaryl ring selected from the group consisting of phenyl, pyridyl, pyrimidyl, 25 pyrazynyl and 1,3,5-triazynyl.
Co..,pounds I.B in which Ab is unsubstituted or substituted 4-pyridyl which carries an unsubstituted or substituted phenoxy radical in the 6 position are also particularly preferred.
Co...~ou~lds I.B in which Ab is unsubstituted or substituted pyrimidinyl which carries an unsubstituted or substituted pyridyloxy radical are furthermore particularly preferred.
35 Compounds I.B in which Ab is unsubstituted or substituted 1,3,5-triazynyl which carries an unsubstituted or substituted phenoxy radical in the 4 position are also particularly preferred.
40 Compounds of the formula I.C
~" CH(UR')COVR'' Xn ~ yc_Ac I.C
where 0050/gs204 ~ 2199~22 R' and R"are each C1-C4-alkyl, X 1s cyano, nitro, halogen, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, f yc is CRY R~-C(=O)-Wc-ic a single or double bond and, in the case of a single bond, the relevant carbon atoms each furthermore carry a hydrogen atom, RY i8 hydrogen or alkyl, 25 R~ i8 hydrogen, cyano, nitro, halogen or alkyl, W is oxygen, sulfur, amino or alkylamino, c is O or 1, f -~ is a bond to Ac and Ac is alkyl, alkenyl, alkynyl or cycloalkyl or is aryl, arylalkyl, arylalkenyl, hetaryl, hetarylalkyl or hetarylalkenyl which is unsubstituted or substituted by conventional groups.
Particularly preferred compounds I.C are those in which yc is CH=C(halogen)-C(=O)-O-~-CGh,~o~nds I.C in which yc i3 CH=C(halogen)-C(=O)-NH-~ are also particularly preferred.
Other particularly preferred cGr-~o~nds I.C are those in which yc 45 is CH=C(halogen)-C(=O)-NH-~-005U/4~:!04 -2199~22 Compounds I.C in which yc is CH=C(halogen)-C(=O)-~ are also particularly preferred.
C~ ounds I.C in which Ac i5 alkyl are furthermore particularl 5 preferred.
Co~ nds I.C in which Ac is alkenyl are also particularly preferred.
10 Other particularly preferred cv,..pGui.ds I.C are those in which Ac is alkynyl.
Compounds of the formula I.D
Xn ~ CH(UR')COVR'' I.D
CH20 C~Ad wherein R' and R"are each Cl-C4-alkyl, X i8 cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is ~ 1 , a C~-Cs-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atom~ of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, ~r . 'Cl-C4--alkyl~Cl-C4--haloalkyl~Cl-C4--alkoxy, ~ Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n i8 ~ I ~ and Ad i8 cycloalkyl which may carry one to four of the following substituents: cyano, halogen, alkyl, haloalkyl or alkoxycarbonyl, or aryl, arylalkyl or arylalkenyl which is unsubstituted or substituted by conventional yLOups ~
are furthermore preferred.
45 Particularly preferred compounds I.D are those in which Ad is unsubstituted or substituted cyclopropyl.
Compounds of the formula I.E
~ " CH(UR')COVR'' Xn ~ I.E
~i ye_Ae where R' and R"are each C1-C4-alkyl, X i8 cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1 , a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl--C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or f butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X ~ay be different when n is > 1, and 25 YQ i s CRa=N--z a_~
Ra is hydrogen, alkyl or haloalkyl or is aryl which is unsubstituted or substituted by conventional groups, 30 za is oxygen, amino or alkylamino, f -# is a bond to Ae and Ae is hydrogen, unsubstituted or substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynylcarbonyl or alkynyloxycarbonyl, unsubstituted or substituted cycloalkyl, heterocyclyl, aryl, arylalkyl, axyloxyalkyl, arylalkenyl, aryloxyalkenyl, arylcarbonyl, aryloxycarbonyl, hetaryl, hetarylalkyl, hetaryloxyalkyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylcarbonyl or hetaryloxycarbonyl, 2I99~22 are furthermore preferred.
Particularly preferred compounds I.E are those in which ye is CH2N-O-~.
C- _~nds I.E in which ye is CH=N-NH-# are also particularly preferred.
other particularly preferred cv~ nds I.E are those in which ye 10 is CH=N-N(CH3)-~.
Compounds I.E in which Ae is alkyl are furthermore particularly preferred.
15 C- E-unds I.E in which AQ is unsubstituted or substituted ( arylalkyl are also particularly preferred.
other particularly preferred ~ vunds I.E are those in which Ae is unsubstituted or substituted hetarylalkyl.
Compounds of the formula I.F
~" CH(UR')COVR'' X~ ~ I.F
CH20-Af where R' and R"are each C1-C4-alkyl, f X is cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy~ C1-C4-alkylthio or, where n is ~ 1, a C3-Cs - alkylene, C3-C5-alkenylene, oxy--C2-C4-alkylene, oxy--Cl-C3--alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-4--alkyl,Cl--C4--haloalkyl,Cl-C4--alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, 0050~45204 2 1 ~ 9 4 2 2 Af is a phthalimido group which is unsubstituted or substituted by conventional group~ or is a radical --N=CRgRh, 5 Rg is hydrogen, halogen, cyano, nitro, unsu~stituted or substituted alkyl, alkenyl or alkynyl or unsubstituted or substituted cycloalkyl, heterocyclyl, aryl or heteroaryl, Rh i8 hydrogen, unsubstituted or substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl and alkynyloxycarbonyl, unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, arylalkenyl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy or ~0 Rg and Rh~ together with the carbon atom to which they are bonded, form cycloalkyl, cycloalkenyl or saturated or partially unsaturated heterocyclyl which i~ unsubstituted or substituted by conventional groups.
35 Compounds I.F in which Rq is alkyl are furthermore particularly preferred.
Other particularly preferred compounds I.F are the those in which Rg is cycloalkyl.
Compounds I.F in which Rq is haloalkyl are also particularly preferred.
Compounds I.F in which Rg is cyano are furthermore particularly 45 preferred.
2199~22 C~r.~po~nds I.F in which Rg is alkylthio are also particularly preferred.
Compounds I.F in which Rg is methyl, ethyl, n-propyl, CYC1O~LO~Y1r 5 trifluoromethyl, cyano or methylthio are also particularly preferred.
Col..~ounds I.F in which Rh is unsubstituted or substituted aryl are furthermore particularly pre~erred.
Compounds I.F in which Rh is unsubstituted or substituted hetaryl are also particularly preferred.
Other particularly preferred co.l.pG~Ilds I.F are those in which Rh f~ 15 is alkyl.
Compounds I.F in which Rh is cyaloalkyl are also particularly preferred.
20 Compounds I.F in which Rh is unsubstituted or substituted phenyl or pyridyl are furthermore particularly preferred.
Compounds of the formula I.G
CH(UR' )COVR' ' Xn ~ I.G
Yg Ag where R' and R" are each C1-C4-alkyl, X is cyano, nitro, halogen, C1-C4-alkyl, Cl-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-Cs-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals: halogen, Cl-C4--alkyl,Cl-C4--haloalkyl,Cl-C4--alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, Y9 is oxygen, sulfur or NRk, Rk is hydrogen, unsubstituted or substituted alkyl, alkenyl or alkynyl or unsubstituted or substituted cycloalkyl, heterocyclyl, aryl or hetaryl, Ag is hydrogen, unsubstituted or substituted alkyl, alkoxy, ( alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl or alkynyloxycarbonyl or unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, aryl~lke~yl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, ~5 aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy, f are furthermore preferred.
Particularly preferred compounds I.G are those in which Y9 is 35 oxygen.
Compounds I.G in which Ag is unsubstituted or substituted aryl are also particularly preferred.
40 Other part~cularly preferred compounds I.G are those in which Ag is unsubstituted or substituted phenyl.
Other particularly preferred c~i"~ou~ds I.G are those in which Ag is unsubstituted or substituted hetaryl.
2I99 1~2 Compounds I.G in which Ag is unsubstituted or substituted alkyl, alkenyl or alkynyl are also particularly preferred.
Co...~u~lds I.G in which Ag is unsubstituted or substituted 5 triazolyl are furthermore particularly preferred.
Co...~ounds of the formula I.H
CH(UR')COVR'' Xn~ I.H
~J~
xhm Ah 15 where R' and R"are each C1-C4-alkyl, X and xh are each cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or, where n is ~ 1, a C3 - C5 - alkylene, C3-Cs--alkenylene,oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2--C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chA;~s in turn may carry one to three of the following radicals: halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy or Cl-C4-alkylthio;
f n is 0, 1, 2 or 3, and the radicals X may be different when n is ~ 1, m is 0, 1 or 2, and the radicals Xh may be different when m is ~ 1, and Ah is hydrogen, cyano, nitro, halogen, unsubstituted or substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenylQxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl or alkynyloxycarbonyl or unsubstituted or substituted cycloalkyl, cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxyalkyl, aryloxyalkoxy, arylalkenyl, arylalkenyloxy, aryloxyalkenyl, aryloxyalkenyloxy, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, aryloxycarbonyloxy, hetaryl, hetaryloxy, hetarylalkyl, hetarylalkoxy, hetaryloxyalkyl, hetaryloxyalkoxy, hetarylalkenyl, hetarylalkenyloxy, hetaryloxyalkenyl, hetaryloxyalkenyloxy, hetarylcarbonyl, hetarylcarbonyloxy, hetaryloxycarbonyl or hetaryloxycarbonyloxy, are furthermore preferred.
Particularly preferred c~ oul,ds I.H are those in which Xh is hydrogen.
Co".~o~nds I.H in which Ah is unsubstituted or substituted aryl are 15 also particularly preferred.
Compounds I.H in which Ah is unsubstituted or substituted hetaryl are furthermore particularly preferred.
20 Other particularly preferred c~ oullds I.H are those in which Ah is substituted alkyl.
Compounds l.H in which Ah is substituted alkenyl are also particularly preferred.
Compounds l.H in which Ah is substituted alkynyl are furthermore particularly preferred.
Compounds I.H in which Ah is phenyl substituted by conventional 30 groups are also particularly preferred.
f Co.,.~o~l.ds of the formula I.K
CH(UR')COVR'' Xn ~ yk_Ak I.K
where 40 R' and R are each Cl-C4-alkyl, X is cyano, nitro, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio or, where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-Cl-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon , .
21991~2 atoms of the phenyl ring, where these chains in turn may carry one to three of the following radicals, halogen, Cl-C4--alkyl,Cl-4--haloalkyl,Cl-C4--alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, yk is C~lRf--ON=CRe--CRd=NO--#, Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted aryl;
15 Rf is hydrogen, alkyl or cycloalkyl;
~f -# i8 a bond to A~, Ak is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C3-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, where these groups may be partially or completely halogenated or may carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, Cl-C6--alkylsulfonyl,Cl-C6--alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6--alkoxy,Cl-C6--haloalkoxy, C1-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, Cl-C6-alkylamino, Cl-C6-alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl--C6-alkylaminothiocarbonyl, C2-C6--alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or hetarylthio, where the aromatic and hetero aromatic radicals in turn may be partially or completely halogenated and~or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6--alkylsulfonyl,Cl--C6--alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6--alkoxy,Cl-C6--haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl--C6--alkylamino,Cl--C6--alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, ~ 2199~22 C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(--NORl)--Zo-R2~
aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, where these groups may be partially or completely halogenated or may carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6--alkylcarbonyl,Cl-C6--alkylsulfonyl, Cl-C6--alkylsulfoxyl,C3-C6-cycloalkyl, Cl-C6--alkoxy, Cl-C6--haloalkoxy,Cl-C6--alkoxycarbonyl,Cl--C6--alkylthio, Cl-C6--alkylamino,di-Cl-C6-alkylamino, Cl-C6--alkylaminocarbonyl,di-Cl-C6-alkylaminocarbonyl, Cl-C6--alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6--alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NORl)-Zo~R
Z i8 oxygen, sulfur or nitrogen, and the nitrogen carries hydrogen or Cl-C6-alkyl, O i8 0 or 1, Rl is hydrogen or Cl-C6-alkyl and R2 i9 hydrogen or Cl-C6-alkyl, are furthermore preferred.
Particularly preferred co.,lpound~ I.K are those in which yk i~
CH2-ON=C ( CH3 ) -C ( alkyl)sN-O-#.
35 Compounds I.K in which yk is CH2-ON=C(CH3)-C(aryl)=NO-~ are also particularly preferred.
Other particularly preferred co.,.~ounds I.K are those in which Y~
i s CH2-ONsC ( CH3 ) -C ( cycloalkyl)=NO-*.
Compounds I.K in which yk is CH2-ON=C ( CH3 ) -C ( hetaryl)=NO-# are also particularly preferred.
Compounds I.K in which yk is CH2-ONsC ( CH3 ) -C ( CH3 ) =NO-# are 45 furthermore particularly preferred.
_ 0050/4520~
so Compounds I.K in which yk is CH2-ON=C ( CH3 ) -C (C6Hs)=NO-~ are also particularly preferred.
Other particularly preferred compounds I.K are those in which Ak 5 is hydrogen or C1-C6-alkyl.
Compounds I.K in which Ak is unsubstituted or substituted arylalkyl, hetarylalkyl, aryloxyalkyl or hetaryloxyalkyl are also particularly preferred.
Compounds I.K in which Ak is unsubstituted or substituted aryl or hetaryl are furthermore particularly preferred.
Compounds I.K in which Ak is methyl or ethyl are also particularly 15 preferred.
other particularly preferred compounds I.K are those in which Ak is unsubstituted or substituted arylalkyl or heteroarylalkyl.
20 Particularly preferred compounds I (or I.A to I.K) are those in which U is oxygen and V is nitrogen or amino.
CG,I-~o~lds I (or I.A to I.K) in which U is amino and V is oxygen are also particularly preferred.
Co~.poul~ds I (or I.A to I.R) in which U i8 aminooxy and V is oxygen are furthermore particularly preferred.
Particularly preferred cvl.,~ou~lds I (or I.A to I.K) are those in 30 which R' is methyl or ethyl, in particular methyl.
other particularly preferred compounds I (or I.A to I.K) are those in which R" is methyl or ethyl, in particular methyl.
35 Further particularly preferred compounds I (or I.A to I.~) are those in which n is O or 1, in particular 0.
With respect to the CH(UR')-COVRn group, the compounds I may be present in the R or S configuration.
, COVR"H
Xn~ J~COVR Xn~ ~UR' (R) (S) U~/4~
~ 51 2199~22 Accordingly, racemates or, where the radical R can assume different spatial forms, isomer mixtures are generally formed in the preparation. These racemates or isomer mixtures can be resolved in to the initial isomers in a -nner known per se.
5 With regard to their biological activity, both the racemates or isomer mixtures and the pure isomers may be used, the pure isomers having a better effect than the racemates or isomer mixtures.
10 With regard to their use, the compounds I listed in the tables below are particularly preferred. Moreover, the groups stated in the tables for a substituent are by themselves (independently of the combination in which they are mentioned) a particularly preferred embo~i -nt of the relevant substituent.
~ 2~9122 Table 1 Compounds of the general formula I.A (n = 0) in which UR' is 5 methoxy, VR" iB methoxy, ya is -CH20-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 2 10 Compounds of the general formula I.A (n = 0) in which UR' i5 ethoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# s bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 3 . 15 ! Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is ethoxy, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
20 Table 4 C~.,.~ounds of the general formula I.A (n = 0) in which UR' is ethoxy, VR" i8 ethoxy, ya i8 -CH2o-$ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 5 Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is methoxy, ya iS -CH2S-~ = bond to Aa) and A~
30 corresponds to one of the groups stated in Table A
f Table 6 Compounds of the general formula I.A (n z 0), in which UR' is 35 ethoxy, VR" is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 7 40 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH=CH- and Aa corresponds to one of the groups stated in Table A
:
005~/45204 2 1 9 ~
Table 8 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH=CH- and Aa corresponds to one of 5 the groups stated in Table A
Table 9 Compounds of the general formula I.A (n = 0), in which UR' is 10 methoxy, VR~' is methoxy, ya is -OCH2-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 10 15 Compounds of the general formula I.A (n = 0), in which UR' is ( ethoxy, VR" is methoxy, ya is -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 11 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
25 Table 12 Co~ G~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i~ -cH2o-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
f Table 13 Col,.poul.ds of the general formula I.A (n = 0), in which UR' i~
methoxy, VR is ethylamino, ya is -CH2o-$ (-# = bond to Aa) and Aa 35 corresponds to one of the groups stated in Table A
Table 14 Compounds of the general formula I.A (n = 0), in which UR' is 40 ethoxy, VR" is ethylamino, ya is -CH20-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 15 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH25-~ (-# = bond to Aa) and 5 Aa corresponds to one of the groups stated in Table A
Table 16 Compounds of the general formula I.A (n = 0), in which UR' is 10 ethoxy, VR" is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa corresponds to one o~ the groups stated in Table A
Table 17 15 Compounds of the general formula I.A (n = 0), in which UR~ is f methoxy, VR~' is methylamino, ya iS -CH=CH- and Aa corresponds to one of the groups stated in Table A
Table 18 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH=CH- and Aa corresponds to one of the groups stated in Table A
25 Table 19 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
r Table 20 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methylamino, ya is -OCH2-# (-~ = bond to Aa) and Aa 35 corresponds to one of the groups stated in Table A
Table 21 Compounds of the general formula I.A (n = 0), in which UR' is 40 methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
0050/45204 ~ I 9 3 1 ~ 2 2199~2 Table 22 Compounds of the general formula I.A (n = 0), in which UR~ is ethylamino, VR" is methoxy, ya iS -CHzO-# (-# = bond to Aa) and A8 5 corresponds to one of the groups stated in Table A
Table 23 Compounds of the general formula I.A (n = 0), in which UR' is 10 methylamino, VR" is ethoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 24 15 cG",~ou.lds of the general formula I.A (n = 0), in which UR' is ! ethylamino, VR" is ethoxy, ya iS -CH20-# ( - ~ a bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 25 Compounds of the general formula I.A (n z 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH2S-~ (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
25 Table 26 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR~' is methoxy, ya i8 -CH2S-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
f Table 27 Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VRn is methoxy, ya is -CH-CH- and Aa corresponds to 35 one of the groups stated in Table A
Table 28 Compounds of the general formula I.A (n s 0), in which UR' is 40 ethylamino, VR" is methoxy, ya iS -CHzCH- and Aa corresponds to one of the groups stated in Table A
0050/45204 2 1 g ~ 1 22 Table 29 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i8 methoxy, ya is -oCH2-# (-# - bond to Aa) and 5 Aa corresponds to one of the groups stated in Table A
Table 30 Co~pounds of the general formula I.A (n = 0), in which UR' is 10 ethylamino, VR" is methoxy, ya is -OCH2-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
!
~ ooso/45204 2193~22 ,, ,, ,, c c a a~ r ~ ~1 ~ _ G O ~ ~ ~ :' -G : C' I ~ C C C C ~1 ~1 ~1 C - C ~ ~ ~1 ~ ~1 S S S S C C C -I
C C ~ 1 S S ~:
., S S S S ~ S
'~' ~ S ~ ~ . J P~ X X
~ ~ ~ P~ a) . o o ~
O O C! l ~1 0 0 0 ~ ~ ~ h El E~ ~ X ~I J
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"~ o~ o ~ ~ ~ d~ Ln ~ r-- ~I ~ o ~ r Ln No. Aa No. Aa No. Aa 36 2,4,6-Trimethylphenyl 271 2-Methyl-5-chlorophenyl 3g7 2-Phenylphenyl o 37 3,4,5-Trimethylphenyl 272 2-Methyl-6-chlorophenyl 398 3-Phenylphenyl ~
38 3-n-Propylphenyl 273 2-Methyl-4-fluorophenyl 399 4-Phenylphenyl o 39 4-n-Propylphenyl 274 2-Methyl-3-bromophenyl 400 2-Phenoxyphenyl 2-iso-Propylphenyl 275 2-Methyl-4-methoxyphenyl 401 4-Phenoxyphenyl 41 3-iso-Propylphenyl 276 2-Methyl-5-methoxyphenyl 402 l-Naphthyl 42 4-iso-Propylphenyl 277 2-Methyl-6-methoxyphenyl 403 2-Naphthyl 43 2,3-Di-isopropylphenyl 278 2-Methyl-4-isopropoxyphenyl 404 9-Anthryl 44 3,5-Di-isopropylphenyl 279 2-Methyl-2,5-dLmethoxyphenyl 405 2-Fluoro-4-ph~noYyphenyl 4-n-Butylphenyl 280 2-Methoxyphenyl 406 3-Fluoro-4-phpnoyyphen 46 4-sec-Butylphenyl 281 3-Methoxyphenyl 407 4-Fluoro-4-rh~noyyphen 47 4-iso-Butylphenyl 282 4-Methoxyphenyl 408 2-Chloro-4-phPnoyyphenyl 48 2-Methyl-4-tert-butylphenyl 283 2-Chloro-5-methylphenyl 409 4-Chloro-4-phenoxyphenyl 49 2-Methyl-6-tert-butylphenyl 284 2-Chloro-4-isopLopylphenyl 410 2-Bromo-4-phenoxyphenyl 2-Methyl-4-isopropylphenyl 285 3-n-P~o~o~y~henyl 411 3-Bromo-4-phenoxyphenyl 51 2-Methyl-4-cyclohexylphenyl 286 3-n-Butoxyphenyl 412 4-Bromo-4-~hPn~yphenyl 52 2-Methyl-4-phenylphenyl 287 3-iso-Butoxyphenyl 413 3-Methyl-1 phenoxyphenyl 53 2-Methyl-4-~enzylphenyl 288 3-n-Pentoxyphenyl 414 4-Methyl-4-phenoxyphenyl 54 3-tert-Butyl-4-phenoxy- 289 4-(Imidazol-l'-yl)phenyl 415 2,5-Dimethylphenyl phenyl ~ 55 2-Methoxy-4-phenoxyphenyl 290 4-(Piperazin-l'-yl)phenyl 416 2-Methyl-4-iodophenyl C~
~3 No. Aa No~ Aa No. Aa O
56 3-Methoxy-4-phenoxyphenyl 291 4-(Morphol; n-l ' - yl)phenyl 417 2-Methyl-5-iodophenyl O
57 4-Methoxy-4-phenoxyphenyl 292 4-(Piperidin-l'-yl)phenyl 418 2,5-Dimethyl-4-iodophenyl 58 3-5-Dichloro-4-phenoxyphenyl 293 4-(Pyridyl-2'-oxy)phenyl 419 2-Me-5-isopropylphenyl o 59 3-4-Dichloro-4-phenoxyphenyl 294 2-Cyclopropylphenyl 420 6-Ethyl-2-pyridyl 4-Ethyl-4-phenoxyphenyl 295 3-Cyclopropylphenyl 421 6-n-Propyl-2-pyridyl 61 4-iso-Propyl-4-phenoxyphenyl 296 3-Cyclohexylphenyl 422 6-iso-Propyl-2-pyridyl 62 2,4-Dimethoxyphenyl 297 4-Cyclohexylphenyl 423 6-n-Butyl-2-pyridyl 63 2,5-Dimethoxyphenyl 298 4-Oxiranylphenyl 424 6-tert-3utyl-2-pyridyl 64 3,6-Dimethoxyphenyl 299 4-(Pyrid-2-yl)phenyl 425 6-n-Phenyl-2-pyridyl 2,3,4-Trimethoxyphenyl 300 3-(Pyrid-2-yl)phenyl 426 6-n-Hexyl-2-pyridyl 66 2-Ethoxyphenyl 301 4-(Pyrid-3-yl)phenyl 427 6-Phenyl-2-pyridyl 67 2-iso-PLopo~y~henyl 302 3-(Pyrid-3-yl)phenyl 428 6-Benzyl-2-pyridyl 68 2-Methyl-3-isopropylphenyl 303 3-(Pyrimid-2-yl)phenyl 429 6-Trifluoromethyl-2-pyridyl 69 2-Methyl-5-isopropylphenyl 304 3-Phenoxyphenyl 430 6-Methoxy-2-pyridyl 2-Benzyloxyphenyl 305 2-Fluoro-3-pheno~yphenyl 431 6-Chloro-2-pyridyl71 3-Benzyloxyphenyl 306 2-Methyl-3-phenoxyphenyl 432 3,6-DLmethyl-2-pyridyl 72 4-Benzyloxyphenyl 307 6-Methyl-2-pyridyl 433 3,6-Diethyl-2-pyridyl 73 4,6-Dimethyl-2-pyridyl 308 5,6-Dimethyl-2-pyridyl 434 4-Phenyl-6-methyl-2-pyridyl 74 4,6-Diphenyl-2-pyridyl 309 3,4-Dichloro-6-methyl- 435 3,4,5~Trichloro- ~3 pyridyl 6-phenyl-2-pyridyl ~
~.
No. Aa No. Aa No. Aa 4-Trifluoromethyl-6-methyl- 310 3-Acetyl-4,6-dimethyl-2- 436 3-Cyano-6-methyl- O
6-2-pyridyl pyridyl 2-pyridyl 76 3-Cyano-6-ethyl-2-pyridyl 311 3-Cyano-6-n-propyl-2-pyridyl 437 3-cyano-iso-pyropyl-2-pyridyl ~
77 3-Cyano-6-cyclo-propyl- 312 3-Cyano-6-n-butyl-2-pyridyl 438 3-Cyano-6-tert-butyl-2-pyridyl 2-pyridyl 78 3-Cyano-6-cyclo-hexyl- 313 3-Cyano-6-phenyl-2-pyridyl 439 3-Methoxycarbonyl-2-pyridyl 6-iso-propyl-2-pyridyl 79 3-Ethoxycar~onyl-6-iso- 314 3-Cyano-4,6-dimethyl-2- 440 3,5,6-Trichloro-propyl-2-pyridyl pyridyl 2-pyridyl 5-Trifluoromethyl-2-pyridyl 315 3-Chloro-5-trifluoromethyl- 441 6-Cyclopropyl-2-pyridyl 2-pyridyl 81 6-Bromo-2-pyridyl 316 4-Trifluoromethyl-5-chloro- 442 4-tert-butyl-2-pyridyl O
2-pyridyl 82 3,6-Bis(trifluoromethyl)- 317 5-Trifluoromethyl-2-pyridyl 443 3-Fluoro-2-pyridyl 2-pyridyl 83 3-Chloro-2-pyridyl 318 4-Bromo-2-pyridyl 444 5-Methyl-2-pyridyl 84 3-Fluoro-5-trifluoromethyl- 319 3,6-Dichloro-5-trifluoro- 445 6-Chloro-4-cyano-2-pyridyl methyl-2-pyridyl 2-pyridyl 4,6-Difluoro-2-pyridyl 320 3,5-Dichloro-6-fluoro-2- 446 6-Methoxy-3-nitro-- pyridyl 2-pyridyl 86 4-Cyano-6-fluoro-2-pyridyl 321 4-Cyano-3,5,6-trifluoro-2- 447 6-Chloro-5-nitro-pyridyl 2-pyridyl 87 4,6-Dicyano-2-pyridyl 322 5-Trichloromethyl-2-pyridyl 448 5-Cyano-2-pyridyl C~
~ 0050/45204 2 1 9 g ~ ~ 2 I
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O ~ O~ O r~ o o o No. Aa No. Aa No. Aa 103 2,3,5,6-Tetrafluoro- 338 2-Pyrimidinyl 464 4,6-Dimethyl- o 4-pyridyl 2-pyrimidinyl 104 4-Trifluoromethyl- 339 4,5,6-Trimethyl- 465 4-Benzyl-6-methyl- ~
2-pyrimidinyl 2-pyrimidinyl 2-pyrimidinyl ~
105 4-Methyl-6-phenyl- 340 4,6-Dimethyl-5-chloro-2- 466 4-Fluoro-2-pyrimidinyl 2-pyrimidinyl pyrimidinyl 106 5-Methyl-2-pyrimidinyl 341 4,6-Difluoro-2-pyrimidinyl 467 4-Pyrimidinyl 107 2,6-Dimethyl-4-pyrimidinyl 342 2,6-Bis-(trifluoromethyl)- 468 2-Chloromethyl-6-methyl-4-pyrimidinyl 4-pyrimidinyl 108 2-Methyl-6-chloromethyl- 343 2-iso-Propyl-6-methyl-4- 469 2-iso-Propyl-6-chloro-4-pyr;~i~;nyl pyrimidinyl methyl-4-pyrimidinyl 109 2-cyclo- Propyl-6-chloro- 344 2-cyclo-Propyl-6-methyl- 470 2-Methyl-6-methoxymethyl-methyl-4-pyrimidinyl 4-pyrimidinyl 4-pyrimidinyl 110 2-iso-Propyl-6-methoxy- 345 2-Phenyl-4-pyri~;~inyl 471 2,5-Dimethyl-methyl-4-pyrimidinyl 4-pyrimidinyl 111 2-Methylthio-6-trifluoro- 346 2-Methylthio-5-chloro- 472 2-Methylthio-5-n-octyl-methyl-4-pyrimidinyl 6-trifluoromethyl-4- 6-methyl-4-pyrimidinyl pyrimidinyl 112 2-Methyl-6-trifluoromethyl- 347 2-n-Propyl-6-trifluoro- 473 2-iso-Propyl-6-tri~luoro-4-pyrimidinyl methyl-4-pyrimidinyl methyl-4-pyrim;~inyl 113 2-n-Propyl-6-methyl- 348 2-tert-Butyl-6-trifluoro- 474 2-Methyl-5-chloro-4-pyrimidinyl methyl-4-pyr;~;~;nyl 6-trifluoromethyl-4-pyrimidinyl 114 2-n-Propyl-5-chloro-6-tri- 349 2-iso-Propyl-5-chloro- 475 2-tert-Butyl-5-chloro-fluoromethyl-4-pyrimidinyl 6-trifluoromethyl-4- 6-trifluoromethyl-pyrimidinyl 4-pyrimidinyl c~
~ 0050/45204 2199 l22 ,~
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Ur-l ~1 _I
Zr ~ r l _I r l ~I r-~ ~I r ~r-~ r l No, Aa No. Aa No. Aa 129 2-Pyrazinyl 364 6-Chloro-2-pyrazinyl 490 5-Methyl-2-pyrazinyl . o 130 3-Pyridazinyl 365 5-Chloro-3-pyri~z; nyl 491 2-Thienyl ~
131 3-Thienyl 366 4-Chloro-3-thienyl 492 2-Chloro-3-thienyl o 132 5-Chloro-3-thienyl 367 4-Chloro-2-thienyl 493 2-Quinoxalinyl 133 3-Methyl-2-quinox~li nyl 368 7r8-Dimethyl-2-quinn~linyl 494 7,8-~ichloro-2-~uinoxalinyl 134 7-Methyl-2-quinoxalinyl 369 8-Methyl-2-~uinoxalinyl 495 7-Methoxy-2-qn; no~; nyl 13S 3-Phenyl-5-isoxazolyl 370 2-BPn~x~olyl 496 2-Benzothiazolyl 136 1-Phenyl-pyrazol-4-yl 371 2-n-Propyl-6-methyl- 497 2-Cyclopentyl-4-pyrimidinyl 6-trifluoromethyl-4-pyrimidinyl 137 2-Cyclohexyl-6-trifluoro- 372 2-Cyclohexyl-5-chloro- 498 2-n-Propyl-5-chloro-methyl-4-pyrimidinyl 6-methyl-4-pyrimidinyl 6-methyl-4-pyrimidinyl 138 Pyrazol-1-yl 373 4-Chlo.opyLazol-1-yl 499 3,5-~imethylpyrazol-1-yl 139 1,2-~Pn7;soxazol-3-yl 374 1-(4-Chlorophenyl)-pyrazol-4 500 1-(4-Methylphenyl)--yl pyrazol-4-yl 140 1-Phenylpyrazol-4-yl 375 1-Methyl-3-trifluoromethyl- 501 1-(4-Fluorophenyl)-pyrazol-5-yl pyrazol-4-yl 141 5-Phenylisoxazol-3-yl 376 Benzotriazol-1-yl 502 3-Cyano-5-nitro-2-pyridyl c~
2 1 9 ~ 2 Table 31 CG..,~oullds of the general formula I.A (n = 0), in which UR' is 5 methoxy, VR" is methoxy, ya iS -CH20-# (-# ~ bond to Aa) and Aa is phenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
10 Table 32 Compounds of.the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(=O)Riii in the 4 position, Riii 15 for a compound corresponding to one of the groups ~tated in Table B
Table 33 20 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-~ (-# = bond to A~) and Aa is phenyl which carries a radical C(=O)Riii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 34 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i8 -CH20~ = bond to Aa) and Aa is 30 phenyl which carries a radical C(=O)Riii in the 3 position, Riil for a c~ oul.d corresponding to one of the yLOU~ stated in Table B
Table 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 40 stated in Table B
Table 36 Compounds of the general formula I.A (n = 0), in which UR~ is 45 ethoxy, VR" i8 methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 4 00~0/45204 219~22 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 37 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i5 methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 3-methylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table B
Table 38 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa~ and Aa is f 3-methylphenyl which carries a radical C(=O)Riii in the 4 - position, Riii for a compound corresponding to one of the groups stated in Table B
20 Table 39 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carrie~ a radical C(=O)Riii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 40 30 Compounds of the general formula I.A (n = 0), in which UR' is f ethoxy, VR" i8 methoxy, ya iS - CH20-# (~~ 5 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a cG,~ u~d corresponding to one of the yL~U~S
stated in Table B
Table 41 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a cv~.~o~nd corresponding to one of the groups stated in Table B
Table 42 Co~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CHzO-# (~~ = bond to Aa) and Aa is 5 2-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 43 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table 3 Table 44 C~l..poul,ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(zO)Riii in the 4 position, Riii for a ~o~ ou~ld corresponding to one of the groups stated in Table B
25 Table 45 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(=O)Riii in the 4 30 position, Riii for a c~ ound corresponding to one of the groups stated in Table B
Table 46 35 CG...~G~lds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
Table 47 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 2-chloro-5-methylphenyl which carries a radical C(=O)Riii in the 4 68 219942~
position, Riii for a cuh.puund corresponding to one of the yLoups stated in Table B
Table 48 Co.,.~oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloLo 5 -thylphenyl which carries a radical C(=O)Riii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table B
Table 49 Compounds of the general formula I.A (n = 0), in which UR' i8 15 methoxy, VR" is methoxy, ya is -CH20-# ~-~ 8 bond to Aa) and Aa i8 ( i-methylphenyl which carries a radical C(=O)Riii in the 5 position, Riii for a compound corresponding to one of the yLOu~
stated in Table B
20 Table 50 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methoxy, ya i5 -CHzO-# (-~ s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(=O)Riii in the 5 25 position, Riii for a co~pound corresponding to one of the yLv~g stated in Table B
Table 51 30 Compounds of the general formula I.A (n = 0), in which UR' ~s methoxy, VR is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(-O)Riii in the 4 position, Riii for a co,,.pvund corresponding to one of the y~uU~S
stated in Table B
Table 52 Compounds of the general for~ula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 40 2,5-dichlorophenyl which carries a radical C('O)Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table B
00~0/45204 21 99ll22 Table ~
No. Riii 10 6 CH3(CH2)4 7 CH3(CH2)s 8 CH2-Cl 9 CH2Br 1 0 CH2CH2Cl 15 11 CH2CH2CH2Cl 12 CH2(CHz)3-C
13 CH2(CH2)4 16 CH2CH2~r 17 CH2CH2CH23r 18 CH2(CH2)3-Br CH2-CH(CH3)2 21 CH2-C(CH3)3 22 CH(CH3)2 30 23 t-~utyl 24 Phenyl f; 2S 2-Pyridyl 26 3-Pyridyl 27 4-Pyridyl 35 28 Cyclopropyl 29 Cyclopentyl Cyclohexyl 40 Table 53 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and A~ is phenyl which carries a radical CHsNORiii in the 4 position, Riii 45 for a cG...~ound corresponding to one of the groups stated in Table C
~ 2I9~2 Table 54 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 5 phenyl which carries a radical CH-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 55 C~ ou.lds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~A..~ou~ld corresponding to one of the groups 15 stated in Table C
Table 56 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" i8 methoxy, ya is -CH20-~ (-# 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a co..~o~lld corresponding to one of the groups stated in Table C
25 Table 57 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH20-# (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH~NORiii in the 4 30 positio~, Riii for a ~ G~nd corresponding to one of the groups f- stated in Table C
Table 58 35 Compounds of the general formula I.A (n = Q), in which UR' is ethoxy, VR" is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical CHsNORiii~in the 4 position, Riii for a col"~ound corresponding to one of the groups stated in Table C
Table 59 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 45 2-chlorophenyl which carries a radical CH=NORiii in the 4 0050~45204 71 2199~22 position, Riii for a-compound corresponding to one of the y stated in Table C
Table 60 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ~LOU~S
10 stated in Table C
Table 61 Cohl~ul~ds of the general formula I.A (n = 0), in which UR' i8 15 methoxy, VR" is methoxy, ya iS -CH2O-~ = bond to Aa) and Aa is f 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a ~or.,pound corresponding to one of the groups stated in Table C
20 Table 62 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VRn is methoxy, ya i5 -CH20-~ (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical CH~NORiii in the 4 25 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 63 30 Compounds of the general for~ula I.A (n = 0), in which UR' i8 l methoxy, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i9 2-methyl-5-chlorophenyl which carries a radical CH=NOR1ii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 64 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya is -cH2O-~ = bond to Aa) and A~ i8 40 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ =
72 2199~22 Table 65 Co~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to A~) and Aa is S 2-chloro-5-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 66 Compounds of the general formula ~.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~--*ound corresponding to one of the groups 15 stated in Table C
f Table 67 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and A~ is 2,5-dichlorophenyl which carries a radical CH=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 68 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CHsNORiii in the 4 ~0 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 69 35 Compounds of the general formula I~A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH-NORiii in the 3 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
Table 70 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 45 phenyl which carries a radical CH=NORiii in the 3 position, Riii 0050/4S204 f 73 219942~
for a co,.,~oulld corresponding to one of the g~oups stated in Table C
Table 71 Compounds of the general formula I.A (n ~ 0), in which UR' is methoxy, VR" is methoxy, ya is -CHzo-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a c~"~ound corresponding to one of the group~
10 stated in Table C
Table 72 Co.l*~unds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR" i8 methoxy, ya i~ -CH20-# ~-# = ~ond to Aa) and Aa is f 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a cv.,~ou,,d corresponding to one of the groups stated in Table C
~0 Table 73 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa is phenyl which carries a radical CtCH3)=NORiii in the 4 position, 25 Riii ~or a cv.ll~oul~d correspondi~g to one of the groups stated in Table C
Table 74 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# - bond to Aa) and Aa i8 phenyl which carries a radical C(CH3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the yLGU~S stated in Table C
Table 75 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 40 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y vU~S
stated in Table C
0050~4~204 219~22 Table 76 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i5 -CH2O-# (-~ = bond to Aa) and Aa i8 5 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 77 Compounds of the general form~ I.A (n - 0), in which UR' is methoxy, VR" ls methoxy, ya iS -CH20-# (~~ = bond to A~) and Aa is 2-fluorophenyl which carries a radical C(CH3)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f ~- Table 78 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C~CH3)=NORiii in the 4 position, Riii for a c~ pc-und corresponding to one of the groups stated in Table C
25 Table 79 Compounds of the general formula I.A (n = o)r in which UR' i methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 30 position, Riii for a ou.l.pound corresponding to one of the groups stated in Table C
Table 80 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-~ = bond to Aa) and A~ is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 81 Cor..~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 45 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 21~22 position, Rlii for a compound corresponding to one of the groups stated in Table C
Table 82 Compounds of the general formula I.A (n = 0), in which UR~ is ethoxy, VR~ i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, R~ii for a co~ v~lld corresponding to one of the yLVU~
10 stated in Table C
Table 83 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is f 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, R~ii for a compound corresponding to one of the groups stated in Table C
20 Table 84 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya i5 -CH20-# (-# o bond to Aa) and A~ is 2-methyl-5-chlorophenyl which carrieq a radical C(CH3)=NORiii in 25 the 4 position, Riii for a mpoulld corre~ponding to one of the groups stated in Table C
Table 85 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)zNORiii in the 4 position, Riii for a cv~,.pound corresponding to one of the groups stated in Table C
Table 86 CG...~v~llds of the general formula I.A (n = 0), in which UR~ is ethoxy, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 40 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co.,.~ound corre~ponding to one of the groups stated in Table C
~ 0050/i5204 2 199~2 Table 87 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 5 2,5-dichlorophenyl which carries a radical C(CH3)SNORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 88 Compounds of the general formula I.A (n 2 0 ) ~ in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C~CH3)=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
r Table 89 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# ~ bond to Aa) and Aa is phenyl which carriQs a radical C(CH3)sN0Riii in the 3 position, Riii for a compound COl L es~onding to one of the groups stated in Table C
25 Table 90 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ G bond to Aa) and Aa i8 phenyl which carries a radical C(CH3)=NORiii in the 3 position, 30 Riii for a compound corresponding to one of the groups stated in r Table C
Table 91 35 CG-.I~oullds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 92 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methoxy, Y~ i8 -CH20-# (-~ - bond to Aa) and A~ is 45 2-methylphenyl which carries a radical C(CH3)-NORiii in the 5 ~ 7 2199 122 position, Riii for a ~vrl~ound corresponding to one of the groups stated in Table C
Table 93 Co,l,~v~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methoxy, ya is -CH20-# (-~ 5 bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups stated in 10 Table C
Table 9~ .
C~ ounds of the general formula I.A (n - 0), in which UR' is 15 ethoxy, VRn is methoxy, ya i5 -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the yLvu~s stated in Table C
20 Table 95 Col..yo~llds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 25 position, Riii for a ~ y~nd corresponding to one of the groups stated in Table C
Table 96 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-* - bond to Aa) and A~ is f 2-methylphenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a c o~nd corresponding to one of the group~
stated in Table C
Table 97 Compounds of the general formula I.A (n = 0), in'which UR' i5 methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
78 2I994~2 Table 98 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 5 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 po~ition, Riii for a c~...pound corresponding to one of the groups stated in Table C
Table 99 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f"
Table 100 Cv.,,~ou.~ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 101 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 102 35 C~ _unds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to onè of the groups stated in Table C
Table 103 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 45 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii 219~ 122 in the 4 position, Riii ~or a cG~ ound corresponding to one of the groups stated in Table C
Table 104 CG.,*oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)zNORiii in the 4 position, Riii for a cG,..~ound corresponding to one of the 10 groups stated in Table C
Table lOS
Compounds of the general formula I.A (n 3 O) ~ in which UR' i8 15 methoxy, VR" is methoxy, ya is -CHzO-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a ~u~ o~.,d corresponding to one of the groups stated in Table C
20 Table 106 CG.II~UndS of the general formula I.A (n = 0), in which UR' is ethoxy, VR~' i8 methoxy, ya iS -CH2û-# (-~ m bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C~CH2CH3)=NORiii 25 in the 4 position, Riii for a c~ Eo~nd corresponding to one of the groups stated in Table C
Table 107 30 Co..,~uunds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i~ methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2,5-dichlorophenyl which carrie~ a radical C(CH2CH3)=NORiii in the 4 position, Rii$ for a compound corresponding to one of the groups stated in Table C
Table 108 Compounds of the general formula I.A (n = 0), in which UR' i5 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 40 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~.,~ou~ld corresponding to one of the groups stated in Table C
219~422 Table 109 CGIlpounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# ( - ~ 5 bond to Aa) and Aa is 5 phenyl which carries a radical C(CH2CH3)sNORiii in the 3 position, Riii for a ~r.,~ound corresponding to one of the groups stated in Table C
Table 110 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
Table 111 Co~ ounds of the general formula I.A (n s 0)~ in which UR' i8 20 methoxy, VR" is methoxy, ya is -CH20~ = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a cv~,.pGu~.d corresponding to one of the groups stated in Table C
25 Table 112 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 30 position, Riii for a cu,..~vul,d corresponding to one of the groups _~ stated in Table C
Table 113 35 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Rii1 for a compound corresponding to one of the groups stated in Table C
Table 114 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 2199~22 position, Riii for a-c~ oul.d corresponding to one of the groups stated in Table C
Table 115 Coh,~oullds of the general formula I.A (n s 0)~ in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~...pou"d corresponding to one of the groups 10 stated in Table C
Table 116 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya iS -CH20-# (-# ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cG~ ound corresponding to one of the groups stated in Table C
20 Table 117 Co...poullds of the general formula I.A (n = 0), in which UR' is methoxy, VR i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i9 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 25 position, Riii for a ~G..~ound corresponding to one of the groups stated in Table C
Table 118 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co~.l~ound corresponding to one of the groups stated in Table C
Table 119 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiLi in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 2~3~2~
Table 120 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is t 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 121 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" ~i8 methoxy, ya is -CH20-# (~~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
,,.
Table 122 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CHzCHzCH3)=NORiii in the 4 position, Riii for a ov,.,~ound corresponding to one of the groups stated in Table C
25 Table 123 Co,~.~vu.lds of the general formula I.A (n = 0), in which UR' is methoxy, VR~' is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii 30 in the 4 position, Riii for a compound corre~ponding to one o~ ~he groups stated in Table C
Table 124 35 Compounds of the general formula I.A (n 5 O) r in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ ~-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ~.ou~s stated in Table C
Table 125 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa i5 45 2-chloro-5-methylphenyl which carrie~ a radical C~CH2CH2CH3)=NOR
2 1 9 9 4 h 2 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 126 Co~ ullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NOR
in the 4 position, Riii for a compound corresponding to one of the 0 yL~S stated in Table C
Table 127 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 128 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiil in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in ~able C
Table 129 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the yLou~s stated in Table C
Table 130 Cor.l~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 40 phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a cG."pound corresponding to one of the groups stated in Table C
-~ ~ 2199~22 Table 131 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O~ s bond to Aa) and Aa is 5 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 132 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya iY -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a cG...~und corresponding to one of the groups 15 stated in Table C
f Table 133 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3) 2 ]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 134 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to AA) and Aa is phenyl which carries a radical C[CH(CH3) 2 ~=N0Riii in the 4 30 position, Riii for a co~ ound corresponding to one of the groups "....... stated in Table C
Table 135 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-~ - bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2~=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 136 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya iS -CH2O-# (-~ - bond to Aa) and Aa is 45 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a-compound corresponding to one of the groups stated in Table C
Table 137 Co...~o~,.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C~cH(CH3)2]sNORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in ~able C
Table 13 C~ ouLlds of the general formula I.A (n = 0), in which UR' i~
15 ethoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is ( 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a c~..,po~lld corresponding to one of the y~OU~S
stated in Table C
ao Table 139 Co~ oul~ds of the general formula I.A (n - 0), in which UR' is methoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CtCH(CH3)2~2NORiii in the 4 25 position, Riii for a cvr,~o~nd corresponding to one of the groups stated in Table C
Table 140 30 Compoundg of the general formula I.A (n = 0), in which UR' is .. ethoxy, VR" is methoxy, ya iS -CH20~ ~ bond to Aa) and AA i5 2-chlorophenyl which carries a radical C[CH(CH3)2]-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 141 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa i8 40 2,5-dimethylphenyl which carrie~ a radical ClCH(CH3) 2 ]=N0R~ii in the 4 position, Riii for a c~ Gund corresponding to one of the groups stated in Table C
0050~45204 219g~22 Table 142 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5 2,5-dimethylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 143 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C[CH(CH3) 2 ] =NORiii in the 4 position, Riii for a ~ ound corresponding to one of the 15 yLOU~ stated in Table C
( Table 144 Co...~ou,~ds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" is methoxy, yn is -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C[ CH ( CH3 ) 2 ] =NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 145 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, vR" i8 methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C[ CH ( CH3 ) 2 ] =NOR~ ii 30 in the 4 position, Riii for a co~pGulld corresponding to one of the -~ groups stated in Table c Table 146 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C[ CH ( CH3 ) 2 ~ =NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 147 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 45 2,5-dichlorophenyl which carries a radical C[CH(CH3)2]=NORiii in ~ 0050/45204 2 1 9 ~ 1 22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 148 Compounds of the general formula I.A (n 2 o)~ in which UR' is ethoxy, VR" is methoxy, ~a iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which ~arries a radical CtCH(CH3)2]~NORiii in the 4 position, Riii for a compound corresponding to one of the 10 groups stated in Table C
Table 149 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa i5 phenyl which carries a radical C[CH(CH3)2]=NORi~i in the 3 position, Riii for a cu~ nd corresponding to one of the groups stated in Table C
20 Table 150 compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical CtCH(CH3)2]=NORiil in the 3 25 position, Riii for a cv".~oulld corresponding to one of the y~o~g stated in Table C
Table 151 -30 C ~o~nds-of the qeneral for~ula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical ClCH(CH3) 2 ]=N0Riii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 152 Compounds of the general formula I.A (n 5 O) ~ in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa i8 40 2-methylphenyl which carries a radical CtCH(CH3) 2 ]-NORili in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
88 2 1 9 9 ~ ~ 2 Table 153 Co~ u~,ds of the general for~ula I.A (n s 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 5 phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a ~~o...~Gund corresponding to one of the groups stated in Table C
Table 154 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i.s methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
Table 155 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a co...poul,d corresponding to one of the groups stated in Table C
25 Table 156 C~ oullds of the general formula I.A ~n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 30 position, Riii for a co~pound corresponding to one of the groups stated in Table C
Table 157 35 Co...~ullds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i~
2-fluorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 158 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 45 2-fluorophenyl which carries a radical C(C6Hs)=NORiii in the 4 ~19~2 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 159 Co~ ul~ds of the general form~ I.A (n 5 O) ~ in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 - position, Riii for a co,.. ~o~lld corresponding to one of the groups 10 stated in Table C
Table 160 Co~ oullds of the general formula I.A (n = 0), in which UR' i5 15 ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to Aa) and Aa is ( 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a c~.l.pour.d corresponding to one of the groups stated in Table C
20 Table 161 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya iS -CH2O-# (-# = bond to Aa) and A~ is 2,5-dimethylphenyl which carries a radical C(C6H5)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 162 30 CG...~ounds of the general formula I.A (n - 0), in which UR' i8 - ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(C6Hg)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 163 Co..,pounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20~ # = bond to Aa) and Aa is gO 2-methyl-5-chlorophenyl which carries a radical C(C6H5)zNORiii in the 4 position, Ri~i for a compound corresponding to one of the groups stated in Table C
2I9~ i~2 Table 164 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5 2-methyl-~-chlorophenyl which carries a radical C(C6H5)eNORiii in the 4 position, Riii for a compound corresponding to one of the ~oup~ stated in Table C
Table 165 C~.,-~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
~. .
Tab~e 166 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Rili for a c~ ulld corresponding to one o~ the groups stated in Table C
25 Table 167 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya is -CH20-# ~~# 5 bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORii~ in the 4 30 position, Riii for a c~ ~ul~d corresponding to one of the groups - stated in Table C
Table 168 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 169 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 45 phenyl which carries a radical C(C6H5)=NORiii in the 3 position, 0050~45204 91 2I99~22 Riii for a compound corresponding to one of the groups stated in Table C
Table 170 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 10 Table C
Table 171 CG.I.~ounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, yA is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the S
position, Riii for a cv...~ound corresponding to one of the groups stated in Table c 20 Table 172 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VR" i8 methoxy, ya i8 -CH20-~ (-# = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 5 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 173 30 Compounds of the general formula I.A (n = 0), in which UR' i9 methoxy, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a ~o~ ound corresponding to one of the groups stated in Table C
Table 174 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-~ ~-# 2 bond to Aa) and Aa is 40 phenyl which carries a radical C(Cl)=NORili in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/45204 2 1 ~ ~ ~ 2 2 Table 175 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 5 2-methylphenyl which carries a radical C(Cl)=NOR111 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 176 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NOR11i in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
.
Table 177 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NOR1l1 in the 4 position, Ri11 for a compound corresponding to one of the groups stated in Table C
25 Table 178 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NORii1 in the 4 30 position, Rii1 for a compound corresponding to one of the groups stated in Table C
Table 179 35 Compounds ol the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NOR1i1 in the 4 position, R1ii for a compound corresponding to one of the groups stated in Table C
Table 180 Compounds of the general formula I.A (n = 0), in which UR' iS
ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 45 2-chlorophenyl which carries a radical C(Cl)=NOR'i' in the 4 position, Riii for a cG..~Gu-ld corresponding to one of the groups stated in Table C
Table 181 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cc...~und corresponding to one of the groups 10 stated in Table C
Table 182 Compounds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR" is methoxy, ya iS -CH20-~ (-# c bond to Aa) and Aa i8 f 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riil for a ~o...~oulld corresponding to one of the groups stated in Table C
20 Table 183 Cv~younds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 184 30 Co...~oullds of the general formula I.A ~n = 0), in which UR' is - ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 185 Compounds of the general formula I.A tn 5 O) ~ in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-chloro 5 -thylphenyl which carries a radical C(Cl)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/~5204 2 I 9 ~ 1 2 ~
Table 186 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 5 2-chlo~o 5 ~ hylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 187 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups lS stated in Table C
( Table 188 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 189 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH20-~ (-# - bond to Aa) and Aa is phenyl which carries a radical C(Cl)sNORiii in the 3 position, Riii 30 for a compound corresponding to one of the groups stated in Table C
Table 190 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a cv...~ound corresponding to one of the groups stated in Table C
Table 191 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 45 2-methylphenyl which carries a radical C(Cl)=NORiii in the S
.
~ 219~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 192 C~ pu~llds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 5 position, Riii for a cG.I.~u~nd corresponding to one of the groups 10 stated in Table C
Table 193 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methoxy, ya i8 -CH20-# ( -# 2 bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~ oul~d corresponding to one of the groups stated in Table C
20 Table 194 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-* = bond to Aa) and A~ is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 195 30 Compounds of the general formula I.A (n = 0), in which UR' is .. methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the group~
stated in Table C
Table 196 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (~~ ~ bond to Aa) and Aa is 40 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~ pound corresponding to one of the groups stated in Table C
21 9~'~2~
Table 197 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 5 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a oo,.,~vund corresponding to one of the ~.o~s stated in Table C
Table 198 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" i-s methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 199 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y~ S
stated in Table C
25 Table 200 Compounds of the general formula I.A (n 2 O) ~ in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to A~) and A~ is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 30 position, Riii for a cor..~ound corresponding to one of the groups -~ stated in Table C
Table 201 35 Compounds of the general formula I.A (n 3 O) ~ in which UR' is methoxy, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, RLii for a compound corresponding to one of the groups stated in Table C
Table 202 Compound~ of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i5 45 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 0050/45204 2 ~ g 9 1 2 2 position, Riii for a-cv~ ound corresponding to one of the groups stated in Table C
Table 203 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH2O~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a ~ ound corresponding to one of the 10 groups stated in Table C
Table 204 C~llpo~nds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is f 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a col"~o~lld corresponding to one of the groups stated in Table C
20 Table 205 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in 25 the 4 position, Riii for a coh.~oul,d corresponding to one of the groups stated in Table C
Table 206 30 Compounds of the general formula I.A (n - 0), in which UR' i8 ,- ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 207 Co..~ounds of the general formula I.A (n 2 O) ~ in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 40 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 21994~
Table 208 .
Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CHzO-# (-# c bond to Aa) and Aa is 5 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cvl,~ound corresponding to one of the groups stated in Table C
Table 209 C~l..pounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and An i5 phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a c~..,pou.ld corresponding to one of the groups stated in 15 Table C
,. .
Table 210 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a c~ o~--d corresponding to one of the groups stated in Table C
25 Table 211 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)2NORiii in the 5 30 position, Riii for a c~ pound corresponding to one of the groups - stated in Table C
Table 212 35 Co.-.~ounds of the general formula I.A (n 5 O) ~ in which UR' i5 ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 213 Compounds of the general formula I.A (n e O) ~ in which UR' is methoxy, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa is 45 phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 OOg~4$~ 4 2199~22 position, Riii for a c~ ou~.d corresponding to one of the groups stated in Table C
Table 214 Co,~.~ou~-ds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 215 . ~~ -Compounds of the general formula I.A (n = O), in which UR' is 15 methoxy, VR is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is ~ 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 216 Compounds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in 25 the 4 position, Riii for a cor..pould corresponding to one of the groups stated in Table C
_ Table 217 30 Compounds of the general formula I.A (n = O), in which UR' is _ methoxy, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 218 Compounds of the general formula I.A (n = O), in which UR' i9 ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 40 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, R~ or a ~o...~ou,~d corresponding to one of the groups stated in Table C
0050~45204 2 1 9 9 ~ 2 2 Table 219 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (~~ = bond to Aa) and Aa is 5 2-chlorophenyl which carries a radical C~cyclopropyl)=NORiii in the 4 position, RiLi for a compound corresponding to one of the groups stated in Table C
Table 220 Co,.,~nds of the general formula I.A (n ~ O), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii ~or a compound corresponding to one of the 15 groups stated in Table C
(r Table 221 Co.~ u.,ds of the general formula I.A (n = 0), in which UR' i8 20 methoxy, VR" is methoxy, Y~ is -CH20-# (-# - bond to A~) and A~ i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NOR~ii in the 4 position, Riii for a co~..po~nd corresponding to one of the groups stated in Table C
25 Table 222 C~.~o~,~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# 5 bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(cyclopropyl)sNORiii 30 in the 4 position, Riii for a ~ o~nd corresponding to one of the f- groups stated in Table C
Table 223 35 Co,.,~ound~ of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, Y~ is -CH2O-# (-~ 8 bond to Aa) and Aa i5 2-methyl-5-chlorophenyl which carries a radical ~
C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 224 Co...pounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i~ -CH20-~ 5 bond to Aa) and Aa is 45 2-methyl-5-chlorophenyl which carries a radical U05U/ 4~
C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 225 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# ( -~ 5 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv...~ound 10 corresponding to one of the groups stated in Table C
Table 226 C~..po~lds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is f~ 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cG.,.pound corresponding to one of the groups stated in Table C
20 Table 227 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii 25 in the 4 position, Riii for a c--~,ound corresponding to one of the groups stated in Table C
Table 228 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-~ (-# = bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 229 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 40 phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a cvr,lpo~nd corresponding to one of the y~U~S
stated in Table C
0050,45204 219~22 Table 230 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# ~-~ = bond to Aa) and Aa is 5 phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a co...~vulld corresponding to one of the groups stated in Table C
Table 231 Co...~o~lds o~ the general formula I.A (n = 0), in which UR' is methoxy, VR".is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
f Table 232 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound c~ ~esponding to one of the groups stated in Table C
25 Table 233 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is phenyl which carries a radical C(CF3)3NORiii in the 4 position, 30 Riii for a Ct, GUnd corresponding to one of the groups stated in !~- Table C
Table 234 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and A~ is phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
gO
Table 235 Compounds of the general formula I.A (n e o), in which UR~ is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and A~ is 45 2-methylphenyl which carries a radical C(CF3)~NORiii in the 4 = = ~ ~
U~S~/4S~4 2 1 9 ~ 2 position, Riii for a compound corresponding to one of the y vu~g stated in Table C
Table 236 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methoxy, ya iS -CH20-# (-# s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii ~or a compound corresponding to one of the groups 10 stated in Table C
Table 237 Compounds of the general formula I.A (n - 0), in which UR' is 15 methoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 238 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VRn i8 methoxy, ya i8 -CH20-# (-~ ~ bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)sNORiii in the 4 25 position, Riii for a coll.pv~nd corresponding to one of the groups stated in Table C
Table 239 30 Compounds of the general formula I.A (n = 0), in which UR' is ,~ methoxy, VR" i8 methoxy, ya is -CH20~ 5 bond to Aa) and Aa is ~ 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a c~.l.pound corresponding to one of the groups stated in Table C
Table 240 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i8 -CH20-# (-# s bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv,,.~oulld corresponding to one of the groups stated in Table C
~ 4~U4 Table 241 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 5 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
Table 242 C~m~ounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups 15 stated in Table C
Table 243 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 244 Co~ ounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH2O-# (-~ - bond to Aa) and Aa i5 2-~ethyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in 30 the 4 position, Riii for a c. --ulLd corresponding to one of the ~- - yL ~3 stated in Table C
Table 245 ~5 Compounds of the general formula I.A (n 5 O) ~ in which UR' i8 methoxy, VR" is methoxy, ya iS -C~20-~ (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ~LoU~s stated in Table C
Table 246 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa is 45 2-chloro 5 ~-thylphenyl which carries a radical C(CF3)=NORiii in U~5~/45~U4 ~ 105 2199~22 the 4 position, R~ for a compound corresponding to one of the groups stated in Table C
Table 247 Compounds of the general formula I.A (n 2 O) t in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-~ = bond to Aa) and Aa i8 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Rili for a ~v.,.~uLld corresponding to one of the groups 10 ~tated in Table C
Table 248 Compounds of the general formula I.A (n = 0), in which UR' is lS ethoxy, VR" is methoxy, ya i8 -CH20-# (~# 5 bond to Aa) and Aa is f 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 249 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, 25 Riii for a ~v..,pound corresponding to one of the y~OU~S stated in Table C
Table 250 30 Compounds of the general formula I.A (n = 0), in which UR' is -- ethoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa ~s phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 251 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa i8 40 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a ~."~und corresponding to one of the groups stated in Table C
2199 1~2 Table 252 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to A~) and Aa is 5 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 253 Compounds of the general formula I.A (n - 0), in which UR' i8 methylamino,.VR" is methoxy, ya i8 -CH20-# (-# 5 bond to Aa) and Aa iB phenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
( Table 254 Compounds of the general formula I.A ~n = 0), in which UR' i8 20 ethylamino, VR~ is methoxy, ya is -CH20-~ (-# = bond to Aa) and A~
is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the yLo~ stated in Table C
25 Table 255 Col..p~ullds of the general formula I.A (n = 0), in which UR' is methylamino, VR~ i8 methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 30 position, Riii for a co...pound corresponding to one of the groups ~- stated in Table C
Table 256 35 C~Lsunds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 257 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ 5 bond to Aa) and 45 Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 ~u:~u~ ~
~99~22 position, Ri~i for a coll.~ou.~d corresponding to one of the groups stated in Table C
Table 258 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 259 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, yA is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 260 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and A~
is 2-chlorophenyl which carries a radical CH=NORiii in the 4 25 position, Riii for a co.,.~ound corresponding to one of the groups 8 tated in Table C
Table 261 30 Co...po~nds of the general formula I.A (n = 0), in which UR' i8 . methylamino, VRn is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 262 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, YR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
OU50/45~4 108 219~ i22 Table 263 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and S Aa is 2-~ethyl-5-chlorophenyl which carries a radical CHeNORiii in the 4 position, Riii for a cu~ u,~d corresponding to one of the groups stated in Table C
Table 264 Compounds of the general formula I.A (n = 0), in which ~R' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~",~ound corresponding to one of the 15 groups stated in Table C
f, Table 265 Cum~ou-.ds of the general Cormula I.A (n = 0), in which UR' i5 20 methyla~ino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a co~ o~nd corresponding to one of th groups stated in Table C
25 Table 266 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carrie~ a radical CH=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
Table 267 35 Cv..,~o~nds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-# ~-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ~l~uyS
stated in ~able C
Table 268 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa 45 is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 ~U~U~45~u~
2 1g9~22 position, Riii for a ~o,lpound corresponding to one of the groups stated in Table C
Table 269 Co...po~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 3 position, Riii for a ~vr,.~ou..d corresponding to one of the groups stated in 10 Table C
Table 270 C~ _vul~ds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa i8 phenyl which carries a radical C~Z~oRiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 271 Compounds of the general formula I.A (n = 0), in which UR' iQ
~ethylamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa iB 2-methylphenyl which carries a radical CH=NORlii in the 25 position, Riii for a cv~ ound corresponding to one of the y ou~
stated in Table C
Table 272 30 Co...poullds of the general formula I.A (n = 0), in which UR' i5 ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 273 Compounds of the general formula I.A (n = 0), in'which UR' is methylamino, VR" i8 methoxy, ya is -CH20-# (-~ = bond to Aa) and 40 Aa i8 phenyl which carries a radical C(CH3)~NOR~i~ in the 4 position, Riii for a cv.,.~oul~d corresponding to one of the yLvU~s stated in Table C
2~99~22 Table 274 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and A~
5 is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 275 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, .VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' ' Table 276 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 277 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a co.,.pvul,d corresponding to one of the groups stated in Table C
. . .
Table 278 35 C pvul.ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -cH2o-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 279 Cv~ ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the ~u~u~ ~v~
~ 111 2199q~2 4 position, Riii for a c~l~.pound corresponding to one of the groups stated in Table C
Table 280 Co~pounds of the general formula I.A ( n ~ O ), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-* (~~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a cG~ und corresponding to one of the groups lO stated in Table C
Table 281 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VRn is methoxy, ya iS -CH2O-# (-# ~ bond to A~) and Aa is-2,5-dimethylphenyl which carries a radical C(CH3)=NORlii in the 4 position, Riii for a c~ v~lld corresponding to one of the groups stated in Table C
2Q Table 282 .
Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 25 4 position, Riii for a cG,..~oul,d correspon~ng to one of the groups stated in Table C
Table 283 30 Compounds of the general formula I.A (n = 0), in which UR' is -- methylamino, VR" is methoxy, ya i5 -CH20~ = bond to Aa) and - Aa i8 2-methyl-5-chlorophenyl which carries a radical C(CH3)~NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 284 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i5 -CH20-# (~~ = bond to Aa) and A~
40 is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=~ORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
., 112 219942~
Table 285 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co".~und correspondiny-to one of the groups stated in Table C
Table 286 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-* (-# = bond to Aa) and A~
is 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
- - .
Table 287 Compounds of the general formula I.A ~n = 0), in which UR' is 20 methylamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa i5 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 288 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a ~o~ ound corresponding to one of the y~OU~S
stated in Table C
Table 289 35 Co.l.pounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the yLOu~s stated in Table C
Table 290 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa 45 is phenyl which carries a radical C(CH3)-NORiii in the 3 position, .
113 2199~22 Ri~i for a compound corresponding to one of the groups stated in Table C
Table 291 s Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in ~he S position, Ri~i for a co...~und corresponding to one of the groups 10 stated in Table C
Table 292 Compounds of the general formula I.A (n - 0), in which UR' i9 15 ethylamino, VR" is methoxy, ya iS -CH20-~ z bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Rii1 for a co~ ound corresponding to one of the groups stated in Table C
20 Table 293 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa i9 phenyl which carries a radical C(CH2CH3)=NORiii in the 4 25 position, Riii for a cG...~oulld corresponding to one of the groups stated in Table C
Table 294 30 Co."p~u.lds of the general formula I.A (n = 0), in which UR' is ethylaminoj VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cG...~ound corresponding to one of the groups stated in Table C
Table 295 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya iS -CH2O-# (-~ = bond to A~) and 40 Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLOU~S stated in Table C
00~0/45204 Table 296 Cu.,.~o~.ds of the general formula I.A (n = 0), in which UR' is ethyl~ino, VR" is methoxy, ya is -CH20-# (-~ ~ bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~..,pou~-d corresponding to one of the groups stated in Table C
Table 297 Cu.l.~uu~lds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, R~ii for a c~..,pound corresponding to one of the 15 groups stated in Table C
( Table 298 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya i~ -CH20 - # (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cG...~Gu~.d corresponding to one of the groups stated in Table C
25 Table 299 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CHzO-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
Table 300 35 Cv~ Gullds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CHzO-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table ~01 Cv...~ou..ds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)-NOR
~S~/4S~4 ~99I22 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 302 Cv.~l~o~.lds of the general formula I.A ~n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv,llp~ulld corresponding to one of the 10 groups stated in Table C
Table 303 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" i8 methoxy, ya i8 -CH20-# (~~ = bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv.ll~v~nd corresponding to one of the groups stated in Table C
~ 20 Table 304 Compounds of the general formula I.A (n s 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to A~) and A~
is 2-methyl-S-chlorophenyl which carries a radical 25 C(CH2CH3)=NORiii in the 4 position, Riii for a cv.,*ound corresponding to one of the yL ~9 stated in Table C
Table 305 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i5 methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa i8 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv.,,~ound corresponding to one of the groups stated in Table C
Table 306 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
40 is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv~ ound corresponding to one of the groups stated ~n Table C
~U5~J45~4 2lgg~22 Table 307 Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and 5 Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups ~tated in Table C
Table 308 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, UR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
(' Table 309 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a cv,,.~ound corresponding to one of the y.~S
stated in Table C
25 Table 310 Compounds of the general formula I.A (n ~ 0), in which UR' i8 ethylamino, VRn is methoxy, ya iS -CH2O-~ (-# = bond to A~) and Aa is phenyl which carries a radical C(CH2CH3)-NORiii in the 3 30 position, Riii for a compound corresponding to one of the y-O~S
. stated in Table C
;...
Table 311 35 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-$ 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 312 Compounds of the general form~ I.A (n - 0), in which UR' is ethylamino, VR~' is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa 45 is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the ~iu:~ù~ ~u~
5 position, Riii for ~ compound corresponding to one of the groups stated in Table C
Table 313 Co"~unds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ e bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 314 Co~ oundq of the general formula I.A (n ~ 0), in which UR' is 15 ethylamino, VR" is methoxy, ya i8 -CH20-# ~-# = bond to Aa) and Aa . is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~ pound corresponding to one of the g- Gup~
stated in Table C
20 Table 315 CGl~o~nds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 25 the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 316 30 C~ ou..ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR'! i8 methoxy, ya is -CH2O~ = bond to A~) and Aa .~ is 2-methylphenyl which carries a radical C(CH2CH2CH3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 317 CG...pou~lds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co~ und corresponding to ~ne of the yL~ups stated in Table C
118 2199~2 Table 318 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa 5 is 2-fluorophenyl which carries a radical C(CB2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 319 Compounds of the general formula I.A (n = 0), in which UR' is methylamino,.VR" is methoxy, ya is -cH2o-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 320 C~.l,poul.ds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 321 Cu,..~ou,lds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ i5 -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical 30 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co...~oulld corresponding to one of the groups stated in Table C
Table 322 35 Compounds of the general formula I.A (n = 0)~ in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLOu~s stated in Table C
Table 323 Co."~unds of the general formula I.A (n = 0), in which UR' i~
methylamino, VR" is methoxy, ya is -CH20-# (-~ ~ bond to Aa) and 45 Aa is 2-methyl-5-chlorophenyl which carries a radical ~S~4~U~ ~ ' ll9 2199~22 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~.,.pG~nd corresponding to one of the groups stated in Table C
Table 324 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and A~
is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound 10 corresponding to one of the groups stated in Table C
Table 325 Co~.,p~unds of the general formula I.A (n = 0), in which UR' is 15 methyl~m; no, VR" is methoxy, ya iS -CH20-# (-~ = bond to AA) and ~~ Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co.~.po~nd cor~esponding to one of the groups stated in Table C
20 Table 326 C~...pou~lds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya i8 -CH20-# (-# - bond to Aa) and A~
is 2-chlo-o 5 ~-thylphenyl which carries a radical 2S C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cvm~n corresponding to one of the yLvu~s stated in Table C
Table 327 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-~ = bond to Aa) and Aa i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 328 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR~ is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa 40 i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ylOU~S stated in Table C
0050/45204 ~'~
120 2 1 9 g 4 2 2 Table 329 Compounds o~ the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 5 Aa is phenyl which carries a radical C(CH2CH2CH3)-NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 330 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ - bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 331 Cu,l.~ounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 332 Co~..pou.lds o~ the general formula I.~ (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-~ 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 30 the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 333 35 CGn.~oullds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i8 methoxy, ya i8 -CH20-# (-$ = bond to Aa) and Aa is phenyl which carries a radical CtCH~CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 334 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa 45 is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 ~ 219g~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 335 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C~CH(CH3) 2 ]~NORiii in the 4 position, Ri1i for a co".~ul,d corresponding to one of the 10 groups stated in Table C
Table 336 Co..,poullds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa ( is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 po~ition, Riii for a c~ ,d corresponding to one of the yLOu~S stated in Table C
20 Table 337 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical ClCH(CH3)2]=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 338 30 Co,.,pou~ds of the general formula I.A (n = 0), ln which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a co,~.~ound corresponding to one of the groups stated in Table C
Table 339 Cor..pounds of the general formula I.A (n - 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-~ (-# - bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical CtCH(CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
122 2 1 9 g 4 2 2 Table 340 C~ u.lds of the general formula I.A ~n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa S is 2-chlorophenyl which carries a radical C~CH(CH3) 2 ]=N0Riii in the 4 position, Ri~i for a cv,..~ound corresponding to one of the groups stated in Table C
Table 341 Cor..~ou~-ds of the general ~ormula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3)2]=NORii~
in the 4 position, Rii~ for a compound corresponding to one of the 15 groups stated in Table C
f Table 342 C~ ullds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya i5 -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C~CH~CH3) 2 ] =NoRiil in the 4 position, Rlii for a c~ u..d corresponding to one of the groups stated in Table C
25 Table 343 Com~u~l,ds of the general fo~ I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 ClCH(CH3)2]2NORiii in the 4 position, Riii for a co~ d corresponding to one of the group~ stated in Table C
. .
Table 344 ~5 Compounds of the general formula I.A (n - 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A' is 2-methyl-5-chlorophenyl which carries a radic~l C~CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 345 Compounds of the general formula I.A (n - 0), in which UR' is methylamino, VR" i5 methoxy, ya iS -CH20-# (-# z bond to Aa) and 45 Aa is 2-chloro-5-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a o~ Gulld corresponding to one o~ the groups stated in Table C
Table 346 Compounds of the general formula I.A (n ~ ~) r in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# ~ bond to Aa) and Aa is 2-chlo-o 5 methylphenyl which carries a radical C~CH(CH3)2]SNORiii in the 4 position, Riii for a cv,,l~ound 10 corresponding to one of the groups stated in Table C
Table 347 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CtCH(CH3)2]=NORiii in the 4 position, Riii for a c~ ou~,d corresponding to one of the groups stated in Table C
20 Table 348 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C[CH(CH3) 2]=NORiii 25 in the 4 position, Riii for a cG",~ound corresponding to one of the groups stated in Table C
Table 349 30 Compounds of the general formula I.A (n = 0), in which UR' is - methyl ~mi no, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is phenyl which carries a radical C~CH(CH3)2]=NORiii in the 3 position, Riii for a co"i~o~,d corresponding to one of the ~LoUps stated in Table C
Table 350 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 351 C~,.,po~llds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-methylphenyl which carries a radical C[CH(CH3)2~=NORi~i in the 5 position, Riii for a compound corresponding to one of the y~O~S stated in Table C
Table 352 Co,..~G~llds of the general formula I.A (n s 0), in which UR' i5 ethylamino, VRI' is methoxy, ya i8 -CH20-~ 3 bond to Aa) and A~
is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 5 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 353 Co".pou~ds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, Y~ is -CH2O-# (-# 5 bond to Aa) and Aa i8 phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a o~ ,u~ld corresponding to one of the yLo~
stated in Table C
25 Table 354 CGh.pG~.lds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6B5)~NORiii in the 4 30 position, Riii for a compound corresponding to one of the yl~U~3 stated in Table C
~.
Table 355 35 Cc ~.~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-# (-# ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 356 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# ~ bond to A~) and Aa 45 is 2-methylphenyl which carries a radical C(C6Hs)2NORill in the 4 219g~22 position, Riii for a-compound corresponding to one of the groups stated in Table C
Table 357 C~ o~l.ds of the general formula I.A (n 2 O) ~ in which UR' i8 methylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6~5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 358 Compounds of the general formula I.A (n = 0), in which UR' i8 15 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa f is 2-fluorophenyl which carries a radical C(C6H5)eNORiii in the 4 position, Riii for a co...~o~nd corresponding to one of the groups stated in Table C
20 Table 359 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to A~) and Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 25 4 position, Riii for a ~c...~ound corresponding to one of the groups stated in Table C
Table 360 30 Ccm~ounds of the general formula I.A (n = 0), in which UR' is ethyl~m~no, VR" is methoxy, ya is -CH2O-# (-# ~ bond to A~) and A~
i8 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 361 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 8 tated in Table C
-~ 126 2199~22 Table 362 Co".~o~nds of the general formula I.A (n o 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-~ (-# - bond to Aa) and Aa 5 is 2,5-dimethylphenyl which carries a radical CtC6H5)=NORiii in the 4 position, Riii for a oG...~vu~ld corresponding to one of the groups stated in Table C
Table 363 Compounds of the general formula I.A ~n 5 O) ~ in which UR' is methylamino,.VR" is methoxy, Y~ is -CH20-# (-# - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C~C6H5)sNORiii in the 4 position, Riii for a compound corresponding 15 to one of the groups stated in Table C
Table 364 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a coll.pound corresponding to one of the groups stated in Table C
25 Table 365 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 30 C(C6H5)=NORiii in the 4 position, Riii for a ~...pound corresponding to one of the groups stated in Table C
Table 366 35 Compounds of the general formula I.A (n 2 o), in which UR' i~
ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a cl -und corresponding to one of the groups stated in Table C
Table 367 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya i5 -CH20-# (-# = bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)=NORi~i in ~ 2199~22 the 4 position, Riii for a c~ pound corresponding to one of the groups stated in Table C
. .
Table 368 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a co,..~ound corresponding to one of the 10 groups stated in Table C
Table 369 Compounds of the general formula I.A (n = 0), in which UR' i8 15 methylamino, VR~ i8 methoxy, ya is -CH20-# (-# = bond to Aa) and ~~ Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the yL~s stated in Table C
20 Table 370 Co."p~unds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, Y~ is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORili in the 3 25 position, Riii for a compound corresponding to one of the groups stated in Table C
.
Table 371 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-~ (-* = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6Hs)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 372 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (~# ~ bond to Aa) and Aa 40 is 2-methylphenyl which carrieR a radical CtC6H5)=NORiii in the 5 position, Riii for a cor.*ol-nd corresponding to one of the groups stated in Table C
~ 219g422 128 _, Table 373 Co~ ou,~dg of the general formula I.A ~n - 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa is phenyl which carries a radical C(Cl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 374 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the g~oups stated in 15 Table C
!
Table 375 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(Cl)=NORii$ in the 4 position, Riii for a cv,.*ou~ld corresponding to one of the groups stated in Table C
25 Table 376 CG..,~oul,ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, Y~ is -CB20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)2NORiii in the 4 30 position, Riii for a compound corresponding to one of the groups - stated in Table C
Table 377 35 C~.ll~ul~ds of the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 378 Compounds of the general formula I.A (n = 0), in which UR' i5 ethylamino, VRn i8 methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa 45 is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 2199~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 379 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)2NORiii in the 4 position, Riii for a cvn~A~ound corresponding to one of the groups 10 stated in Table C
Table 380 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VRn is methoxy, yrA is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cvA..Avv~nd corresponding to one of the groups stated in Table C
20 Table 381 Cu~ o~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,S-dimethylphenyl which carries a radical C(Cl)=NORiii in 25 the 4 position, Riii for a coA..A~ûund corresponding to one of the groups stated in Table C
Table 382 30 CG..,Auoullds of the general ~ormula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 383 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-# (-# = bond to ArA) and 40 Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)-NORiii in the 4 position, Riii for a c~A..A~o~nd corresponding to one of the groups stated in Table C
Uu~4~u~
2199~22 Table 384 Co~ oullds of the general formula I.A (n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa 5 is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 385 Co...~o~nds of the general formula I.A (n = 0), in which UR' is methylamino,.VR" is methoxy, ya iS -cH2o-# ~-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cG...~ound corresponding to one of the 15 groups stated in Table C
f Table 386 Compounds of the general formula I.A (n = 0~, in which UR' is 20 ethylamino, VR~ i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 387 CG,..poul,ds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)2NORiii in 30 the 4 position, Riii for a compound corre~ponding to one of the groups stated in Table C
Table 388 35 Cor..~ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORi~i in the 4 position, Riii for a compound corresponding to one of the ~LoU~s stated in Table C
Table 389 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and 45 Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 ~, 2199122 position, Riii for a c~".pound corresponding to one of the groups stated in Table C
Table 390 Co.,.pou~.ds of thè general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# 5 bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 10 Table C
Table 391 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and ( Aa i8 2-methylphenyl which carries a radical C(Cl)~NORiii in the 5 position, Riii for a c~r..~ou"d corresponding to one of the groups stated in Table C
20 Table 392 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 5 25 position, Riii for a cv~..poul.d corresponding to one of the groups stated in Table C
Table 393 30 Co...~o~nds of the general formula I.A (n - 0), in which UR' is methylamino, VR~ is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)~NOR1ii in the 4 position, Riii for a compound corresponding to one of the yLOU~8 stated in Table C
Table 394 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# - bond to Aa) and Aa 40 is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 395 CG~I~PO~ dS of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and 5 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cor.lp~und corresponding to one of the groups stated in Table C
Table 396 Co.l.~ou~ds of the general formula I.A (n = 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiil in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
!
Table 397 Compounds of the general formula I.A (n = 0), in which UR' i8 20 methylamino, VRn is methoxy, ya i8 -CH20-# (-~ - bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups stated in Table C
25 Table 398 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 30 position, Riii for a compound corresponding to one of the yLVU~S
stated in Table C
Table 399 35 Compounds of the general formula I.A (n = o)~ in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to A~) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 400 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
45 is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 ~ 2199~22 position, Riii for a ~ o~nd corresponding to one of the groups stated in Table C
Table 401 s Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# ~-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cv...~vund corresponding to one of the 10 groups stated in Table C
Table 402 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya i8 -CH20-# (-* = bond to Aa) and Aa f is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table ~03 Compounds of the general ~ormula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl whiah carries a radical 25 C(SCH3)=NORiii in the 4 position, Riii for a cv,.,~o~nd corresponding to one of the groups stated in Table C
Table 404 30 CG---~o~nds of the general formula I.A (n 5 0), in which UR' is .. ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 405 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -c~20-# (-* = bond to Aa) and 40 Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a o~...~o~nd corresponding to one of the groups 3tated in Table C
2199~22 Table 406 C~ oul~ds of the general formula I.A (n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# c bond to Aa) and Aa 5 is 2-chloro-5-methylphenyl which carries a radical C(SCH3)sNORiii in the 4 position, Riii for a cv...~ound corre~ponding to one of the groups stated in Table C
Table 407 Compounds of the general formula I.A (n = 0), in which.UR' is methylamino,.VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 408 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, R~ii for a compound corresponding to one of the groups stated in Table C
25 Table 409 Co~ ounds of the general formula I.A (n = 0), in which UR' is methylamino ~ VRn iB methoxy, ya is -CH20 - ~ ( ~# Q bond to Aa) and Aa is phenyl which carries a radical C(SCH3)-NORiii in the 3 30 positionr Riii for a co...~oulld corresponding to one of the ~ou~s - stated in Table C
Table 410 35 Compounds of the general formula I.A (n - o)~ in which UR' i8 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 411 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 219g~22 5 position, Riii for a c _~ul~d corresponding to one of the y ou~s stated in Table C
Table 412 Compounds of the general formula I.A (n = O), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)'NORiii in the 5 position, Riii for a c~po-~d corresponding to one of the groups 10 stated in Table C
Table 413 Compounds of the general formula I.A (n = O), in which UR' is 15 methylamino, VRn is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carrie~ a radical C(cyalopropyl)~NOR~ii in the 4 position, Riii for a cG.,.~ou.ld corresponding to one of the groups stated in Table C
20 Table 414 Co...p~ul,ds of the general for~ I.A (n = O), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and A~
is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 25 position, Riii for a cv~ ound corresponding to one of the y~S
stated in Table C
Table 415 30 ~ -unds of the general formula I.A (n = O), in which UR' is methylamino, VR" i8 methoxy, ya iS -CH20-$ (-# ~ bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a ~c...~ound corresponding to one of the groups stated in Table C
Table 416 Compounds of the general formula I.A (n = O), in which UR' is ethylamino, VR is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa 40 is 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
219g~22 Table 417 Compounds of the general formtll~ I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-fluorophenyl which carries a radical C(cyclopropyl)=NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 418 Compounds of the general formula I.A (n = 0), in which UR' i5 ethylamino, V.R~' is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and A~
is 2-fluorophenyl which carries a radical c(cyclopropyl)=NoRiii in the 4 position, Riii for a cG~ d corresponding to one of the 15 groups stated in Table C
f Table 419 Co..l~ounds of the general form~ I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to A~1 and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 420 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
i8 2-chlorophenyl which carries a radical C(cyclopropyl)-NOR~ii in 30 the 4 position, Riii for a compound corresponding to one of the - groups stated in Table C
Table 421 35 C~r~.~Gunds of the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya is -CH20-~ (-# 3 bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical ~
C(cyclopropyl)=NORiii in the 4 position, Riii for a ~v.l*o~l.d corresponding to one of the y-OU~S stated in Table C
Table 422 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to A~) and Aa 45 is 2,5-dimethylphenyl which carries a radical 2l99~22 C(cyclopropyl)=NORiii in the 4 position, Riii for a c _u~ld corresponding to one of the groups stated in Table C
Table 423 Coh.~ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a co...~Gu~.d 10 corresponding to one of the groups stated in Table C
Table 424 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa ! is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 po~ition, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 425 C.~ oullds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chlo~o 5 methylphenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 position, Riii for a cGI..~Gund corresponding to one of the groups stated in Table C
Table 426 30 Compounds of the general formula I.A (n = 0), in which UR' is f ethylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv,.lpound corresponding to one of the groups stated in Table C
Table 427 Co..l~ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and 40 Aa is 2,S-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Rii~ for a compound corresponding to one of the groups stated in Table C
2199~22 Table 428 Compounds of the general formula I.A (n ~ 0), in which UR' i8 ethylamino, VR" is methoxy, ya is -CH20-~ (-# 5 bond to Aa) and Aa 5 is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)-NORiii in the 4 po~ition, Riii for a ~ ound corresponding to one of the groups stated in Table C
Table 429 Cv...pGunds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORlii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 430 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 431 CG.-~ounds of the general formula I.A (n c 0)~ in which UR' is methylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii 30 in the 5 position, Riii for a c~l..~Gund corresponding to one of the groups stated in Table C
.~
Table 432 35 CGLI-pvunds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 433 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ 5 bond to Aa) and 45 Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 _ ~ 139 2199~22 position, Riii for a-compound corresponding to one of the y~ups stated in Table C
Ta~le 434 s Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a coh.~und corresponding to one of the groups stated in 10 Table C
Table 435 C~,..pounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and I Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 436 CG...pounds of the general formula I.A (n = 0), in which UR' i~
ethylamino, VR" i8 methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carrie~ a radical C(CF3)=NORLii in the 4 25 position, Riii for a cG..~ou~ld corresponding to one of the groups stated in Table C
Table 437 30 CoAI-pG~nds of the general formula I.A (n = 0), in which UR' is r methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y-OU~5 stated in Table C
Table 438 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-fluorophenyl which carries a radical C~CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
140 2199~22 Table 439 Co...~ullds of the general formula I.A (n e 0)~ in which UR' is methylamino, VR" is methoxy, ya i~ -CH20~ = bond to Aa) and 5 Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 440 Compounds of the general formula I.A (n = 0), in which UR' i8 ethylamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv...~ound corresponding to one of the group 15 stated in Table C
f Table 441 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamlno, VR" i8 methoxy, Y4 i8 -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups ~tated in Table C
25 Table 442 Co.l~you.lds of the general formula I.A (n = 0), in which UR' i~
ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the ~.ou~s r stated in Table C
Table 443 35 CG..~u..ds of the general formula I.A (n = 0), in which UR' i8 methylamino, VRn is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv...~oul~d corresponding to one of the groups stated in Table C
Table 444 CGr~l~o~nds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-~ (-X = bond to Aa) and Aa 45 is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv.,.pound corresponding to one of the groups stated in Table C
Table 445 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i5 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Rili for a cvm~G~l-d corresponding 10 to one of the groups stated in Table C
Table 446 Compounds of the general formula I.A (n = 0), in which UR' is lS ethylamino, VR is methoxy, ya i5 -CH20-~ (-# = bond to A~) and Aa f is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NOR~ii in the 4 position, Riii for a c~."poulld corresponding to one of the groups stated in Table C
20 Table 447 CG",POUndS of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 448 30 CG...~ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 449 Compounds of the general formula I.A (n = 0), in which UR' i~
methylamino, VR" is methoxy, ya iS -CH20-# (~~ = bond to Aa) and 40 Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a co."po~id corresponding to one of the groups stated in Table C
Table 450 Compounds of the ~eneral formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa 5 is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 451 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methylamino, VR" i8 methoxy, ya iS -CH20-# (-# = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CF3)-NORiii in the 5 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 452 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethylamino, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and A~
is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 453 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, 30 Riii for a ~ -u~.d corresponding to one of the groups stated in r Table C
~, Table 454 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# z bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 455 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-# (-~ - bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 2I99~22 position, Riii for a c~ ou"d corresponding to one of the groups stated in Table C
Table 456 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a ~v~..~o~nd corresponding to one of the groups 10 stated in Table C
Table 457 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VRn is methylamino, ya is -CHzO-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a co...~Gul.d corresponding to one of the groups stated in Table C
20 Table 458 CGl,.~Gunds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 25 position, Riii for a co...pG~nd corresponding to one of the groups stated in Table C
Table 459 30 Compounds of the general formula I.A (n = 0), in which UR' is - methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa $s 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 460 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-chlorophenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~...pGund corresponding to one of the groups stated in Table C
Table 461 Co~ oullds of the general formula I.A (n ~ 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-$ = bond to Aa) and 5 Aa is 2,5-dimethylphenyl which carries a radical CH=NOR~ii in the 4 position, Riii for a co..l~ound corresponding to one of the ~-u~s stated in Table C
Table 462 Compounds of the general formula I.A (n = 0), in which UR' is ethûxy, VR" is methylamino, ya is -CH2O-~ (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f Table 463 Compounds of the general formula I.A (n - 0), in which UR' i8 20 methoxy, VR" is methylamino, ya is - CH20-# t-# 2 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 464 CGr~.poul,ds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH2o-$ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carrie~ a radical CH=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the -- groups stated in Table C
Table 465 35 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -CH20-# (-~ 5 bond to Aa) and Aa i8 2-chloro-S-methylphenyl which carries a radical CH=NORiii ~n the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 466 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20~ 2 bond to Aa) and Aa 45 is 2-chloLo 5 methylphenyl which carries a radical CH2NO~iii in - ' ~
14.5 2199~22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 467 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methyla~ino, ya i8 -CH20~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH-~ORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 468 Compounds of the general formula I.A (n 5 0), in which UR' is 15 ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa r is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 20 Table 469 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya i8 -CH20-# (-~ 8 bond to A~) and Aa is phenyl which carries a radical CH=NORiii in the 3 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 470 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-# (-~ = bond to A~) and Aa is phenyl which carries a radical CHsNORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 471 Co~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ ~-# = bond to Aa) and 40 Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
.
0050~45204 Table 472 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# 5 bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical CH-NORiii in the 5 position, Riii for a co,l,~o~nd corresponding to one of the groups stated in Table C
Table 473 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' .
Table 474 Col.*o~l,ds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 47~
Compounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya i5 -C~20-~ (-$ ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups , stated in Table C
Table 476 35 Compounds of the general formula I.A (n 2 O) r in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)~NORiii in the 4 position, Riii for a compound corresponding to onè of the groups stated in Table C
Table 477 Compounds of the general formula I.A (n 2 O) r in which UR' is methoxy, VR" is methylamino, yA is -CH20-~ = bond to Aa) and 45 Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the ~50~4S~U4 219~922 4 position, Riii for a cv~..pound corresponding to one of the groups stated in Table C
Table 478 Co...~ourlds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups 10 stated in Table c Table 479 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methylamino, Y~ i8 -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a cG.,.~ou~d corresponding to one of the groups stated in Table C
20 Table 480 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH2O-# (-~ = bond to Aa) and A~
is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 481 30 CGll.~ounds of the general formula I.A (n = 0), in which UR' is f methoxy, VR" is methylamino, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical CtCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table c Table 482 Co.ll~ourlds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-~ = bond to Aa) and Aa 40 is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLO~S
stated in Table C
005~/45204 148 2199~22 Table 483 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" is methylamino, ya i8 -CH20-# ~-# = bond to Aa) and 5 Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 484 Cu...pG~ds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR~' is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORii~
in the 4 position, Riii for a c~ ound corresponding to one of the 15 groups stated in Table C
Table 485 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VRN is methylamino, ya i8 -CH20-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a CVA.~ Id corresponding to one of the groups stated in Table C
25 Table 486 C- ,ou~lds of the general form~ I.A ~n 5 O) ~ in which UR' is ethoxy, VRn is methylamino, Y~ is -CH20-# (-# = bond to Aa) and Aa is 2-chloLo 5 -thylphenyl which carries a radical C(CH3)=NORiii 30 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 487 3S Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co...~o~nd corresponding to one of the groups stated in Table C
Table-488 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
45 is 2,5-dichlorophenyl which carries a radical C(CB3)=NORiii in the 2199~22 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 489 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa i8 phenyl which carries a radical CtCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 490 . ~.~
Co~ oul,ds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, Y~ is -CH2O-# (-# 5 bond to Aa) and Aa f is phenyl which carries a radical C(CH3)-NORili in the 3 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
20 Table 491 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)-NORiii in the 25 5 position, Riii for a ~~oLI~o~.d corresponding to one of the groups stated in Table C ~.
", . . .
Table 492 30 Compounds of the general formula I.A (n = O), in which UR' is f ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
~. is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 493 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-# - bond to Aa) and 40 A~ i8 phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~mpound correspo~ding to one of the groups stated in Table C
~ 2199 122 Table 494 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# ~ bond to Aa) and AA
5 is phenyl which carries a radical C(CH2CH3)~NORi~i in the 4 position, Riii for a compound corresponding to one of the y- OU~8 stated in Table C
Table 495 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR".is methylamino, ya iS -CH20-~ (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
' Table 4g6 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, Y~ is -CH20-~ (-# = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)~NORili in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 497 Compounds of the general formula I.A (n = 0), in which UR' i~
methoxy, VR is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a ~ ound corresponding to one of the groups stated in Table C
Table 498 35 C~ -o~ ds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and A~
is 2-fluorophenyl which carries a radical C(CH2CH3)-NORii~ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 499 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya iS -CH20-# (-# = bond to Aa) and 45 Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in ~ /45~4 ~ 151 2199 1 22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 500 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cor..p~u~,d corresponding to one of the groups lO stated in Table C
Table 501 Cu..,~ounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methylamino, ya is -CH2O-~ s bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 502 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR i8 methylamino, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 503 30 Compounds of the general formula I.A (n 8 O) ~ in which UR' is methoxy, VRn is methylamino, ya i~ -CH2O-# (-# = bond to Aa) and f Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 504 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH2O-~ (-# = bond to A~) and Aa 40 is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a com~und corresponding to one of the groups stated in Table C
2199~22 Table 505 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methyl A~ no~ ya is -CH20-# (-# = bond to Aa) and 5 Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 506 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, yn is -CH20-# (-# = bond to Aa) and Aa i~ 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a .G~ und 15 corresponding to one of the groups stated in Table C
Table 507 C~...pou,lds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methylamino, ya is -CH20-# (-~ 5 bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a ~o,~.pouI,d corresponding to one of the groups stated in Table C
25 Table 508 C~..pounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya iS -CH20-~ (-# = bond to Aa) and A~
is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the . groups stated in Table C
Table 509 35 Co...~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methyl~mino, ya is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a col.,~ound corresponding to one of the groups stated in Table C
Table 510 Co...~oullds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR~ is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 45 is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 153 2 1 g 9 ~ 2 2 position, Riii for a-co~ nd corresponding to one of the ~LO~S
stated in Table C
.
Table 511 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a c~".~ound corresponding to one of the 10 groups stated in Table C
Table 512 C~ ounds of the general formula I.A (n z 0), in which UR' is 15 ethoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and Aa f is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 513 C~-..~ounds of the general for~~ I.A (n 2 O) ~ in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORli~ in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 514 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 515 CG...~ounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya iS -CH20-~ = bond to Aa) and 40 Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ ourld corresponding to one of the groups stated in Table C
.
~ ~19912~
Table S16 Co...~o~l~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ oul~d corresponding to one of the y.uu~S stated in Table C
Table 517 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR".is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORii~ in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
( Table 518 Compounds of the general formula I.A (n 3 O) ~ in which UR' i8 20 ethoxy, VR" i8 methylamino, ya iS - CH20-~ (~# e bond to Aa) and AA
is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound correspon~;~g to one of the groups stated in Table C
25 Table 519 CG...~ul.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in 30 the 4 position, Riii for a cG,..~o~"d corresponding to one of the group~ stated in Table C
. .
Table 520 35 Compounds of the general formula I.A (n = 0), in which UR' i5 ethoxy, VR" i8 methylamino, ya is -CH20-# (-~ - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 521 Compounds of the qeneral formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -CH20-# (-# 2 bond to Aa) and 45 Aa is 2,5-dimethylphenyl which carries a radical .
UU~U~ 4~U~
2199~22 CtCH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 522 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CHzCH2CH3)=NORiii in the 4 position, Rlii for a compound corresponding to one of the 10 groups stated in Table C
Table 523 Co~ ou,~ds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methylamino, ya is -CH20-# (-# = bond to Aa) and f~ A~ is 2-methyl-5-chlorophenyl which carrie~ a radical - C(CH2CH2CH3)=NORlii in the 4 posit~on, Riii for a cv.,.~und corresponding to one of the groups stated in Table C
20 Table 524 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 25 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv,.,~vund corresponding to one of the groups stated in Table C
Table 525 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv...~o~r.d corresponding to one of the groups stated in Table C
Table 526 Cv.ll~ounds of the general formula I.A (n = 0), in~which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv...~nd corresponding to one of the groups stated in Table C
OU50/4S~4 2~99~22 Table 527 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, yn iS -CH20-# (-# = bond to Aa) and S Aa i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ o~lld corresponding to one of the groups stated in Table C
Table 528 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya i9 -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORlii in the 4 position, Riii for a compound corresponding to one of the 15 y~OU~S stated in Table C
Table 529 Cu...~u~ds of the general formula I.A (n - 0), in which UR~ i3 20 methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a co.,.~ou.d corresponding to one of the groups stated in Table C
25 Table 530 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 30 position, Riii for a cu~ ou..d corresponding to one of the y ~s stated in Table C
Table 531 35 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methoxy, VR" is methylamino, ya iS -CH20-~ 5 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a c~ ound corresponding to one of the y r o~s stated in Table C
Table 532 Cull.~ou,lds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, Y~ is -CH20-# (-~ - bond to Aa) and Aa 45 is 2-methylphenyl which carries a radical C(CH2CH2CH3)sNORili in 2~99 122 the 5 position, Riii for a c~ u--d corresponding to one of the groups stated in Table C
Table 533 Cu..*ou.,dg of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya is -CH20-# (-# z bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 position, Riii for a ov,..~ulld corresponding to one of the ~- uU~8 10 stated in Table C
Table 534 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa ! i8 phenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a cou.~ d corresponding to one of the yLOU~S
stated in Table C
20 Table 535 Co~ oul~ds of the general formula I.A (n - 0), in which UR' is methoxy, VRn is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in 25 the 4 position, Riii for a co"~und corresponding to one of the groups stated in Table C
Table 536 30 Compounds of the general formula I.A (n 2 0)~ in which UR' is {- ethoxy, VR" is methylamino, ya i5 -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a cv".~ound corresponding to one of the groups stated in Table C
Table 537 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical CtCH(CH3)2]=NORiii in the 4 position, Ri~i for a cvl..~oulld corresponding to one of the groups stated in Table C
Table 538 CG1..~0UndS of the general formula I.A (n - O), in which UR' i9 ethoxy, VR" is methylamino, Y~ is -cH2o-# (-~ - bond to Aa) and Aa 5 is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NOR~ii in the 4 position, Riii for a co,.,~ound corresponding to one of the groups stated in Table C
Table 539 Co,..~ou.lds of the general fo~mlll? I.A (n - O), in which UR' is methoxy, VR".is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-chlorophenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a cv,.l~ound corresponding to one of the 15 groups stated in Table C
Table 540 Compounds of the general formula I.A (n ~ O), in which UR' is 20 ethoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C[CH(CH3)z]=NORiii in the 4 position, Riii for a c~ G~nd corresponding to one of the groups stated in Table C
25 Table 541 Com~ounds of the general formula I.A (n e O) ~ in which UR' is methoxy, VR" i8 methylamino, ya iS -CH20~ bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3)2]=NOR
30 in the 4 position, Riii for a compound corresponding to one of the oups stated in Table C
Table 542 35 Compounds of the general formula I.A tn = O), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3) 2 ] =NOR~ii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 543 Compounds of the general formula I.A (n = O), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and 45 Aa is 2-methyl-5-chlorophenyl which carries a radical ClCH(CH3)2]=NORiii in the 4 position, Ri~i for a co,..~o~lld corresponding to one of the groups stated in Table C
Table 544 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i9 methylamino, ya iS -CH20-# (-~ z bond to Aa) and A' i8 2-methyl-5-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a cv,.*o~nd 10 corresponding to one of the groups stated in Table C
Table 545 Co,.*oul~ds of the general formula I.A (n - 0), in which UR' is lS methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and ( Aa is 2-chloro-5-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the ylo~s stated in Table C
20 Table 546 CG,--~o~uds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya i8 -CH20-~ (-# = bond to Aa) and Aa is 2-chloro-5-~ethylphenyl which carries a radical 25 C[CH(CH3)2]2NORiii in the 4 position, Riii for a c~ ~und corresponding to one of the yLOup~ stated in Table C
Table 547 30 Compounds of the general formula I.A (n = 0), in which UR' is ~-- methoxy, VRn is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C~CH(CH3)2]=NORi~i in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 548 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# z bond to Aa) and A~
40 is 2,5-dichlorophenyl which carries a radical C[CH(CH3)2]zNORiii in the 4 position, Rili for a COI oul~d corresponding to one of the groups stated in Table C
2193~22 Table 549 Co..,~oul~ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH2O-# (-# - bond to Aa) and 5 Aa i5 phenyl which carries a radical C~CH(CH3) 2 ]=NORiii in the 3 position, Riii for a c~l"pound corresponding to one of the groups stated in Table C
Table 550 Co~ ou.,ds of the general form~ I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-~ = bond to Aa) and Aa is phenyl which carrie~ a radical CtCH(CH3)2~=NORiii in the 3 position, Riii for a compound corresponding to one of the yL~U~
15 stated in Table C
(~
Table 551 Compounds of the general formula I.A (n - 0), in which UR' i8 20 methoxy, VR" is methylamino, ya i8 -CH2O-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C~CH(CH3) 2 ]=NORiii in the 5 position, Riii for a co...~und corresponding to one of the yLUU~S stated in Table C
25 Table 552 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamlno, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=NORiii in 30 the 5 position, Riii for a ~c..~ound corresponding to one of the groups stated in Table C
Table 553 35 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 554 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH20-# ( ~~ 5 bond to Aa) and Aa 45 is phenyl which carries a radical C(C6H5)=NOR~i~ in the 4 --0050/45204 2 1 9 g '1 2 2 position! Riii for a cc...y~und corresponding to one of the g-ou~s stated in Table C
Table 555 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# t-~ s bond to Aa) and An is 2-methylphenyl which carries a radical C(C6Hs)=NORili in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 556 Compounds of the general formula I.A (n - 0), in which UR' i8 15 ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the y GU~S
stated in Table C
20 Table 557 CG...~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6H5)=NORi~i in the 25 4 position, Riii for a c _ou"d corresponding to one of the groups stated in Table C
Table 558 30 Compounds of the general formula I.A (n = 0), in which UR' i8 ~- ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa ~ is 2-fluorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 559 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/,5204 2 1 9 9 1 2 2 Table 560 Compounds of the general formula I.A (n o 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa 5 is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 561 Co".~G~,lds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR".is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a ~v...~ound corresponding to one of the 15 groups stated in Table C
f Table 562 Compounds of the general formula I.A (n 2 O) ~ in which UR' is 20 ethoxy, VR" is methylamino, ya iY -CH20~ # = bond to Aa) and A~
i8 2,5-dimethylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 563 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# 5 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 C(C6H5)sNORiii in the 4 position, Riii for a c~..pGund corresponding to one of the groups stated in Table C
.
Table 564 35 Cu.,.~o~nds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# 2 bond to Aa) and Aa is 2-~ethyl-5-chlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 565 Compounds of the ~eneral formula I.A (n = 0), in which UR' i~
methoxy, VR" is methylamino, ya iS -CH20-# (-~ e bond to Aa) and 45 Aa is 2-chloro-5-~ethylphenyl which carries a radical ~ 2199~22 C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 566 s Compounds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a co,..~o~.,d corresponding to one of the 10 groups stated in Table C
Table 567 Compounds of the general formula I.A (n = O), in which UR' is 15 methoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and ! . Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 568 Compounds of the general formula I.A (n - O), in which UR' is ethoxy, VR" i8 methylamino, ya iS -CH20-# (-# - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in 25 the 4 position, Riii for a cor,.~ohnd corresponding to one of the groups stated in Table C
Table 569 30 Compounds of the general formula I.A (n = O), in which UR' is r methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the y O~B
stated in Table c Table 570 Co~ vunds of the general formula I.A (n = O), in which UR' iB
ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa 40 is phenyl which carries a radical C(C6H5)=NOR~ii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
00~0/45204 ~ 2199~22 Table 571 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-# (-# = bond to Aa) and S A~ is 2-methylphenyl which carriQs a radical C(C6H5)-NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 572 C~ oul,ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i.s methylamino, ya iS -CH20~ = bond to A~) and Aa is 2-methylphenyl which carries a radical C~C6Hs)-NORili in the 5 position, Riii for a compound corresponding to one of the yLO~
15 stated in Ta~le C
¢'.
Table 573 Cu.l*ounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR is methylamino, Y~ is -CH20-# (-~ = bond to AA) and Aa is phenyl which carries a radical C(Cl)~NORiii in the 4 position, Riii for a compound corresponding to one of the yLOU~S
stated in Table C
25 Table 574 Compounds of the general formula I.A (n 5 O) ~ in which UR' is ethoxy, VR" i~ methylamino, ya iS -CH20-# (-# ~ bond to Aa) and A~
i8 phenyl which carries a radical C(Cl)=NORiii in the 4 position, 30 Riii for a compound corresponding to one of the yrO~p~ stated in f Table C
Table 575 35 Compounds of the general formula I.A (n = o)r in which UR' is methoxy, VR" is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORi~i in the 4 position, Riii for a compound corresponding to one of the y r O~pS
stated in Table C
Table 576 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
45 is 2-methylphenyl which carries a radical C(Cl)=NORi~i in the 4 OU50~452~4 ~ 2199~22 position, Riii for a compound corresponding to one of the ylOu~
stated in Table C
Table 577 Compounds of the general formula I.A (n 5 0)~ in which UR' is methoxy, VR~' is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)sNORiii in the 4 position, Riii for a cv...~ound corresponding to one of the groups 10 stated in Table C
Table 578 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and Aa (' i8 2-fluorophenyl which carrie~ a radical C(Cl)=NORili in the 4 position, Riii for a cc...~ound corresponding to one of the groups stated in Table C
20 Table 579 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 25 position, Riii for a co...~v~nd corresponding to one of the yLOU~S
stated in Table C
Table 580 30 Cor.-~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i5 methylamino, ya is - C~20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~5 Table 581 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# ( -# 5 bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(Cl)zNORiii in the 4 position, Ri~i for a cv..,po~nd corresponding to one of the yLOu~S stated in Table C
~able 582 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20~ 5 bond to Aa) and Aa 5 is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, R~ii for a c~ oulld corresponding to one of the groups stated in Table C
Table 583 C~ o~nds of the general formula I.A (n = 0), in which UR' i9 methoxy, VR" is methylamino, ya iS -CH20~ 5 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cvmpound corresponding to one of the 15 groups stated in Table C
Table 584 Cu...~ul~ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a c~ o~.d corresponding to one of the groups stated in Table C
25 Table 585 Co.--~v~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii 30 in the 4 position, Riii for a cv...~ound corresponding to one of the f~ groups stated in Table C
_ Table 586 35 Compounds of the general formula I.A (n 5 0), in which UR' is ethoxy, VR" is methylamino, ya iS - CH20-# ( -~ 5 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 587 Compounds of the general formtll~ I.A (n = 0), in which UR' is methoxy, VR" is methylamino, Y~ is -CH20-# (-~ = bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in , U~/4~4 2199~2~
the 4 position, Riii for a co~ ound corresponding to one of the groups stated in Table C
Table 588 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a co".~oulld corresponding to one of the groups 10 stated in Table C
Table 589 Compounds of the general formula I.A (n = 0), in which UR' is lS methoxy, VR" is methylamino, Y~ i8 -CH20-# (-~ = bond to Aa) and f A~ is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a c~",~oulld corresponding to one of the groups stated in Table C
20 Table 590 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(Cl)sNORiii in the 3 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 591 30 Compounds of the general formula I.A (n = 0), in which UR' i5 ~- methoxy, VR" is methylamino, ya iS - CH20-~ 5 bond to Aa) and Aa is 2-methylphenyl which carrie~ a radical C(Cl)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 592 Compounds of the general formula I.A (n = 0), in'which UR' is ethoxy, VRn is methylamino, ya iS -cH2o-# (-~ = bond to Aa) and Aa 40 is 2-methylphenyl which carries a radical C(Cl)2NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
~ = ==
2199~22 Table 593 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and 5 Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 594 Compounds of the general formula I.A (n e ~)r in which UR~ i5 ethoxy, VR i8 methylamino, ya iS -CH20-~ (-# e bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cv..,poul.d corresponding to one of the groups 15 stated in Table C
~, Table 595 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methyl pm~ not ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cGr~ und corresponding to one of the groups stated in Table C
25 Table 596 C o~l~ds of the general for~ I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and A~
is 2-methylphenyl which carrie~ a radical C(SCH3)~NORiii in the 4 30 position, Riii for a .~G~ o~nd corresponding to one of the groups stated in Table C
Table 597 35 Compounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" i5 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and A~ is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 598 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-~ (-# = ~ond to A~) and Aa 45 is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 2199~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 599 Cc..~p~ul.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i~ -CH2O-# (-# = bond to Aa) and A~ i8 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y.OU~S
10 stated in Table C
Table 600 Co.~ unds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, ya iS -CH20-# (-$ - bond to Aa) and Aa ~' iY 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~r..~ound corresponding to one of the groups stated in Table C
20 Table 601 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR i8 methylamino, ya is -CH20-# (-# z bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in ~5 the 4 position, Riii for a compound corresponding to one of the g~uups stated in Table C
Table 602 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya iS -CH2O-# (-~ = bond to Aa) and A~
is 2,5-dimethylphenyl which carries a radical C(SCH3)=NOR~ii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 603 C~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~' is methylamino, ya iS -CH2O-# (-# = bond to Aa) and 40 A~ is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Rii~ for a cv~.~oui,d corresponding to one of the groups stated in Table C
~050/45204 2199~22 Table 604 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa 5 is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co.,~pou.~d corresponding to one of the groups stated in Table C
Table 605 Compounds of the general formula I.A (n - 0), in which ~R' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)-NORiii in the 4 position, Riii for a ~o-..pou,.d corresponding 15 to one of the groups stated in Table C
Table 606 Cum~ounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)~NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 607 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR is methylamino, ya i~ -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
., Table 608 35 C~..,poullds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and A~
is 2,5-dichlorophenyl which carries a radical C(~CH3)=NORiii in the 4 position, Riil for a c~...pound corresponding to one of the groups stated in Table C
Table 609 CG,..~o~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and 45 Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a cv..,~ound corresponding to one of the groups stated in Table C
Table 610 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# t-# ~ bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 611 Cor~o~..ds of the general formula I.A (n - 0), in which UR~ is 15 methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to A~) and ' Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 position, Riii for a ov~ o~nd corresponding to one of the ~o~s stated in Table C
.
20 Table 612 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 25 position, Riii for a co,..p~und corresponding to one of the y~u~S
stated in Table C
Table 613 30 Compounds of the general formula I.A (n = 0), in which UR' i8 f methoxy, VR" is methylamino, yn is -CH20-# (-~ = bond to Aa) and A~ is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv~ ound corresponding to one of the groups stated in Table C
Table 614 Compounds of the general formula I.A (n = 0), in which UR ' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa 40 is phenyl which carries a radical c(cyclo~ro~yl)=NoRiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
00~0/45204 219g422 Table 615 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# s bond to A~) and 5 Aa is 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a co.~,~ou~-d corresponding to one of the yL~U~S stated in Table C
Table 616 C~",~o~nds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a c~ o~lld corresponding to one of the 15 groups stated in Table C
Table 617 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" i8 methylamino, ya is -CH20-~ (-# 5 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiil in the 4 position, Rili for a ov~ o~nd corresponding to one of the groups stated in Table C
25 Table 618 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ 2 bond to A~) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f yLGUyS stated in Table C
,, ~
Table 619 35 CoL.~oullds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cG..~pound corresponding to one of the yLoups stated in Table C
Table 620 Compounds of the general formula I.A (n = o)~ in which UR~ is ethoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and A~
45 is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in 0050/45204 2 1 9 ~ l 2 2 the 4 position, Riii for a-~o~ ou.ld corresponding to one of the groups stated in Table C
Table 621 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" i8 methylamino, ya is -CH20-# ( -# 2 bond to Aa) and Aa i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound 10 corresponding to one of the ~L0~8 stated in Table C
Table 622 Cul,-~ounds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cvl.-~o~nd corresponding to one of the groups stated in Table C
20 Table 623 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa i5 2-methyl-5-chlorophenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 pO8 ition, Riii for a cG~ ound corresponding to one of the groups stated in Table C
Table 624 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -cH2o-# (-~ - bond to Aa) and An is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a co".~ound corresponding to one of the y~u~s stated in Table C
Table 625 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR~ is methylamino, ya is -cH2o-# (-~ = bond to Aa) and 40 Aa is 2-chloro-5-~ethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
u~ 4~
219~22 Table 626 Co..,~ul.ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa 5 i8 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 627 Co~ ourlds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound 15 corresponding to one of the groups stated in Table C
Table 628 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VRn is methylamino, ya i8 -CH20~ bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(cycloplo~yl)=NoRiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 629 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR~ is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 30 3 position, Riii for a compound corresponding to one of the groups f stated in Table C
Table 630 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a compound corresponding to onè of the ~LOU~8 stated in Table C
Table 631 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i5 -CH20-# (-~ = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NOR
~U/4~
in the 5 position, Riii for a cvr,,~ound corresponding to one of the groups stated in Table C
Table 632 CGm~oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORi~i in the 5 position, Riii for a c~m~ound corresponding to one of the 10 groups stated in Table C
Table 633 CG",~ounds of the general formula I.A (n = 0), in which UR' is lS methoxy, VR" is methylamino, ya is -CH2O-# (-# = bond to Aa) and ( A~ i8 phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a ~o."~ound corresponding to one of the groups stated in Table C
20 Table 634 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 position, 25 Riii for a cv,,,~ou.ld corresponding to one of the ~ou~s stated in Table C
Table 635 30 Compounds of the general formula I.A (n - 0), in which UR' i5 methoxy, VRn is methylamino, Y~ is -CH2O-~ (-# 8 bond to A~) and ~ A~ i3 2-methylphenyl which carries a radical C(CF3)=NoRi~$ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 636 Compounds of the general formula I.A (n = 0), in 'which UR' is ethoxy, VR" is methylamino, ya is -CH2O-~ = bond to Aa) and A~
40 is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a c~ poul,d corresponding to one of the yLou~s stated in Table C
4~
Table 63~ -Co.,.~ounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20~ # = bond to Aa) and 5 Aa is 2-fluorophenyl which carries a radical C(CF3)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 638 CG~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' Table 639 Col,.~,ounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the y-vU~S
stated in Table C
25 Table 640 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 30 position, Riii for a compound corresponding to one of the groups ~- stated in Table C
., Table 641 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cr oulld corresponding to one of the groups stated in Table C
Table 642 Cv~ ou..ds of the general formula I.A (n = 0), in which UR' i~
ethoxy, VR" is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa 45 is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the ~199422 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 643 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CtCF3)=NORiii in the 4 position, Riii for a compound corresponding 10 to one of the groups stated in Table C
Table 644 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR~ is methylamino, ya is -CH20-~ ( -# 3 bond to Aa) and Aa ( is 2-methyl-5-chlorophenyl which carries a radical C(CF3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 645 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH20-# (-# ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 25 C(CF3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 646 30 Co...pounds of the general formula I.A (n = 0), in which UR' i ethoxy, VR" i8 methylamino, ya iS -CH20-~ = bond to Aa) and Aa ' ~ i8 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 647 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and 40 Aa is 2,5-dichlorophenyl which carries a radical C(CF3)-NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
~U~4~u4 Table 648 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 5 is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 649 Co...~ ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the y~O~S
15 stated in Table C
~,..
Table 650 Col.lpoul,ds of the general formula I.A (n s 0), in which UR' is 20 ethoxy, VRn is methylamino, ya is -cH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a cuL,.puu~d corresponding to one of the groups stated in Table C
25 Table 651 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, vR~ is methylamino, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)3NORiii in the 30 5 position, Riii for a cv...~oulld corresponding to one of the groups ~- stated in Table C
. , Table 652 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the S
position, Rlii for a compound corresponding to onè of the groups stated in Table c 179 21 ~9 122 Table C
5 No. Riii No. Riii 1 H 30 2-Cl-C6H4-CH2 2 CH3 31 3-Cl-C6H4-CH2 3 CH3CH2 32 4-Cl-C6H4-CH2 4 CH3CH2CH2 33 2,5-Cl2-C6H3-CH2 10 5 CH3CH(CH3) 34 2-CH3-C6H4-CH2 6 ~CH3)3C 35 3-CH3-C6H4-CH2 7 CH2=CH-CH2 36 4-CH3-C6H4-CH2 8 HC_C-CH2 37 2,3-(CH3)2-C6H3-CH2 15 9 CH30CH2CH2 38 2,4-(CH3)2-C6H3-CH2 ( 10 Cyclo~lO~yl-cH2 39 2,4,6-(CH3)3-C6H2-CH2 11 CH2=CH-CH2-CH2 40 2,4,6-(CH3)3-C6H2-CH2 12 CH3-cH=cH-cH2 41 2-CF3-C6H4-CH2 20 13 CH3-(CH2)3 42 3-CF3-C6H4-CH2 14 CH3-(CH2) 4 43 4-CF3-C6H4_CH2 CH3-(CH2)5 44 2-cF3-5-cH3-c6Hs-cH2 16 Cyclohexyl 45 2-CH3-5-CF3-C6H3-CH2 2-CH3-Cyclohexyl 46 2-Br-C6H4-CH2 18 CH3-CH2-C(CH3)2 47 2-(iso-Propyl)-C6H4-CH2 19 CH3-cH(cH3)-cH2 48 2-(iso-Propyl)-3-Cl-C6H3-CH2 CH3-CH(CH3)-CH2-CH2 49 2-CH3-5-~-C4-Hs-C6H3-CH2 21 CH2=c(cH3)-cH2 50 2-CH3-5-t-C4Hg-C6H3-CH2 30 22 HC-C-C~CH3)=CH-cH2 51 3-CH3-5-t-C4Hs-C6H3~cH2 23 Cl(CH3)-C=CH 52 2-Cl-5-t-C4Hg-C6H3-CH2 24 CH2=c(cl)-cH2- 53 3-cl-5-t-c4H9-c6H3-cH2 ClCH=CH-CH2- 54 2-OCH3-C6H4-CH2 35 26 C6Hs-CH2 3-OCH3-C6H4-CH2 28 3-F-C6H4-CH2 57 3-cH3-5-ocH3-c6H3-cH2 29 4-F-C6H4-CH2 58 3-Cl-5-0CH3-C6H3-CH2 Table 653 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 45 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 UV~4~4 position of the oxad-iazolyl ring and Xn corresponding for each co..,~ound to a line of Table D
Table 654 Compounds of the general formula I.A in which UR' i5 ethoxy, VR"
is methoxy, ya iS -CH2S-# (-$ e bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the cnmh;nAtion of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each 10 c~ ound to a line of Table D
Table 655 Compounds of the general formula I.A in which UR' i8 methylamino, 15 VRn i8 methoxy, ya i8 -CH2S-# (~~ - bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the co~hinAtion of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each co...pGund to a line of Table D
20 Table 656 CG...pounds of the general formula I.A in which UR' is ethylamino, VR" i8 methoxy, ya is -CH2S-# t-# = bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 25 position of the oxadiazolyl ring and Xn corresponding for each ~r..~oulld to a line of Table D
Table 657 30 Co,..~unds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-# (-~ = bond to Aa) and A~ is - 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 658 Compounds of the general form11l A I.A in which UR' is ethoxy, VRn is methylamino, ya is -CH2S-# (-~ = bond to Aa) and A~ is 40 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each c~..*ound to a line of Table D
2199~22 Table 659 Compounds of the general formula I.A in which UR' i8 methoxy, VR~
i8 methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each ~o,.,~u..d to a line of Table D
Table 660 Compounds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each 15 compound to a line of Table D
f Table 661 Compounds of the general formula I.A in which UR' i8 methylamino, 20 VR" is methoxy, Y~ is -CH2S-# (-# = bond to Aa) and Aa i8 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn correspon~;ng for each c~m~ound to a line of Table D
25 Table 662 Compounds of the general formula I.A in which UR' is ethyl ~ml n VRn is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 30 position of the thiazolyl ring and Xn corresponding for each f compound to a line of Table D
, , , Table 663 35 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-~ (-# = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each coh,~und to a line of Table D
gO
Table 664 Col"~ou~lds of the general formula I.A in which UR' is ethoxy, VR~
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and A~ is 45 thiazol-2-yl, the combination of the substituent in the 4 UUS~45~U4 ~ 182 2199~22 position of the thiazolyl ring and Xn corresponding for each c~...~ou~,d to a line of Table D
Table 665 Compounds of the general formula I.A in which UR' is methoxy, VRn iB methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substi~uent in the 4 position of the thiazolyl ring and Xn corresponding for each 10 ~ ~o~l~d to a line of Table D
Table 666 Co,l-~ou~ds of the general formula I.A in which UR' i8 ethoxy, VR
15 is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each o~ ound to a line of Table D
ZO Table 667 Col..~o~nds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and Aa is thiazol-~-yl, the combination of the substituent in the 4 25 position of the thiazolyl ring and Xn corresponding for each cv...~ound to a line of Table D
Table 668 30 Co~.~ounds of the general formula I.A in which UR' is ethylamino, f VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i8 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 669 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa i8 40 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each co~ ound to a line of Table D
2199~22 Table 670 Compounds of the general formula I.A in which UR' i8 ethoxy, VR~
i5 methylamino, ya is -CH20-~ (-# s bond to Aa) and Aa is 5 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corxesponding for each compound to a line of Table D
Table 671 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa i3 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each 15 co...~o~-d to a line of Table D
( Table 672 Co...po~nds of the general formula I.A in which UR' is ethoxy, VR~
20 is methoxy, Y~ is -cH2o-# (-~ = bond to A~) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 673 Co...~oullds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 30 position of the thiazolyl ring and Xn corresponding for each f~ compound to a line of Table D
Table 674 35 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each co~ ound to a line of Table D
Table 675 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methylamino, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 45 5-methylthiazol-4-yl, the combination of the substituent in the 2 = :
~U~ / 4~
position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 676 Col.Lpounds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 677 Compounds of the general formula I.A in which UR' is methoxy, VR~
15 is methoxy, ya iS -cH2s-# (-~ = bond to Aa) and Aa is oxazol-2-yl, ¢~ the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each co..,~und to a line of Table D
20 Table 678 Co...pou"ds of the general form~ I.A in which UR' is ethoxy, VR~
is methoxy, ya iS -CH2S-# (-~ = bond to A~) and Aa i8 oxazol-2-yl, the cn~h~n~tion of the substituent in the 4 position of the 25 oxazolyl ring and Xn corresponding for each oo..~ound to a line of Table D
Table 679 30 C~".~o~l,ds of the general formula I.A in which UR' is methyl~no, ~- VR" is methoxy, Y~ is -CH2S-~ ~ bond to Aa) and A~ is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 680 CG.,~ou.-ds of the general formula I.A in which URr is ethylamino, VR" is methoxy, ya is -CH2S-~ = bond to Aa) and Aa is 40 oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each ~o.l,~ou..d to a line of Table D
Table 681 Compounds of the general formula I.A in which UR' is methoxy, VR
is methylamino, ya is -CH2S-# (-# = bond to Aa) and Aa i~
5 oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 682 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH2S-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a 15 line of Table D
~, Table 683 Compounds of the general formula I.A in which UR' is methoxy, VR"
20 is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 684 Compounds o~ the general formula I.A in which UR' is ethoxy, VRD
is methoxy, ya is -CHzO-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the 30 oxazolyl ring and Xn corresponding for each c~...pound to a line of Table D
. .
Table 685 35 Compounds of the general formula I.A in which UR' i8 methylamino, VRn iS methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 686 Compounds of the general formula ~.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 45 oxazol-2-yl, the comh; n~tion of the substituent in the 4 position .
186 2199~22 of the oxazolyl ring and Xn corresponding for each ~~...pound to a line of Table D
Table 687 Co~ oul~ds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa is oxazol-2-yl, the comh;~Ation of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each c~ ound to a 10 line of Table D
Table 688 Compounds of the general formula I.A in which UR' i8 ethoxy, VR
15 is methylamino, ya is -CH~0-# (-# = bond to Aa) and Aa is f oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 689 Compounds of the general ~ormula I.A in which UR' is methoxy, VR"
is methoxy, ya iS -CH2S-# (-~ = bond to A~) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 25 position of the oxadiazolyl ring and Xn corresponding for each ~ IGuud to a line of Table D
Table 690 30 Compounds of the general formula I.A in which UR' iB ethoxy, VR"
- is methoxy, Y~ is -CH2S-# (-~ = bond to Aa) and Aa iB
1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 691 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 40 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
~ 2199~22 Table 692 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 693 Co"~ou"ds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya iS -CH2S-# (-# - bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each 15 ~o.,.pound to a line of Table D
f Table 694 Compounds of the general formula I.A in which UR' i8 ethoxy, VRn 20 is methylamino, ya is -cH2s-# (-~ = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oyA~ ~zolyl ring and Xn corresponding for each co..,pound to a line of Table D
25 Table 695 C~...pounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 30 position of the oxadiazolyl ring and Xn corresponding for each -- cG,,,~ou.. d to a line of Table D
Table 696 35 Compounds of the general formula I.A in which UR' i8 ethoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 697 C~ ounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 45 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 ~J U :~ U ~
~ 2199~122 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 698 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the co~h;n~tion of the substituent in the 3 position o~ the oxadiazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 699 Compounds of the general formula I.A in which UR' is methoxy, VR"
15 is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is f 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 700 C~...~o~nds of the general formul~ I.A in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 25 position of the oxadiazolyl ring and Xn corresponding for each co..,~ound to a line of Table D
Table 701 30 Compounds of the general formula I.A in which UR' is methoxy, VR~
~-- is methoxy, ya is -CH2S-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 702 Co...~Gunds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is - CH2S~ 5 bond to Aa) and Aa is 40 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
2199!122 Table 703 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each c~ oulld to a line of Table D
Table 704 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH2S-# (-# z bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each 15 cG...~oul,d to a line of Table D
f Table 705 Compounds of the general formula I.A in which UR' is methoxy, VR~
20 i5 methylamino, ya iS -cH2s-# (-# = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 706 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya i8 -CH2S-$ (-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 30 3 position of the thiadiazolyl ring and Xn corresponding for each ~ compound to a line of Table D
, . , Table 707 35 Compounds of the general formula I.A in which UR' i8 methoxy, VR~
is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 708 Compounds of the general formula I.A in which UR' i5 ethoxy, VR"
is methoxy, ya is -CH20-~ (-# 3 bond to Aa) and Aa is 45 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 0050~45204 -2199~22 3 position of the thiadiazolyl ring and Xn corresponding for each ~vm~ound to a line of Table D
Table 709 S
CG...pou~lds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya i5 -CH20-# (-# = bond to A~) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each 10 c~l..pound to a line of Table D
Table 710 Cu~ ul~ds of the general formula I.A in which UR' is ethylamino, 15 VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compo~l.d to a line of Table D
20 Table 711 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH20-# (-# e bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 25 3 position of the thiadiazolyl ring and Xn corresponding for each co".~oul,d to a line of Table D
Table 712 30 C~ oullds of the general formula I.A in which UR' i8 ethoxy, VRn f- is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is " 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the th; ~i azolyl ring and Xn corresponding for each cG.,.~oul~d to a line of Table D
Table 713 Co~ ou~lds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -cH2s-# (-# 2 bond to Aa) and Aa is 40 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each ~o..,~o~.ld to a line of Table D
2199!122 Table 714 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is metho~y, ya iS -CH2S-# (-# ~ bond to Aa) and Aa is 5 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 715 C~ o~..ds of the general formula I.A in which UR' is methylamino, VR" i8 methoxy, ya is -cH2s-# (-~ 5 bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 15 c~"l~ou~.d to a line of Table D
!' Table 716 Cv."~o~l-ds of the general formula I.A in which UR' is ethylamino, 20 VRn is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding ~or each compound to a line of Table D
25 Table 717 Compounds of the general formula I.A in which UR' i9 methoxy, VR
is methylamino, ya is -cH2s-# t-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the S
30 position of the isoxazolyl ring and Xn corresponding for each ,~ col-~ound to a line of Table D
Table 718 35 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH2S-# (-~ = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each cG.I*ound to a line of Table D
Table 719 Compounds of the general formula I.A in which UR' is methoxy, VR
is methoxy, ya iS -CH20-~ 5 bond to Aa) and Aa is 45 isoxazol-3-yl, the combination of the substituent in the 5 2199~22 position of the isoxazolyl ring and Xn co~Lesponding for each compound to a line of Table D
Table 720 Co~~unds of the general formula I.A in which UR' is ethoxy, VRn is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 10 c~ ound to a line o~ Table D
Table 721 Compounds of the general formula I.A in which UR' is methylamino, 15 VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 722 Compounds of the general formula I.A in which UR' i8 ethylamino, VRn i8 methoxy, ya iS -CH20-~ = bond to Aa) and Aa is isoxazol-3-yl, the cnmh~ n~tion of the substituent in the 5 25 position of the isoxazolyl ring and Xn corresponding for each c~ ~ul~d to a line of Table D
Table 723 30 Compounds of the general formula I.A in which UR' is methoxy, VRn ~- is methylamino, ya i8 -CH20-~' (-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 724 Co."~u.,ds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-$ (-~ = bond to Aa) and Aa is 40 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each c~r..~o~,ld to a line of Table D
ooso/45204 2 1 9 9 ~ 2 2 Table 725 Compounds of the general formula I.A in which UR' i5 methoxy, VR"
is methoxy, ya iS -CH2S-~ (-# = bond to Aa) and Aa is 5 isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each cv.,~ound to a line of Table D
Table 726 Cv.~.~o~nds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each 15 compound to a line of Table D
r Table 727 C Junds of the general formula I.A in which UR' is methylamino, 20 VR" is methoxy, ya iS -CH2S-# (-# - bond to Aa) and A~ is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each cu~ und to a line of Table D
25 Table 728 Co,..~ullds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya iS -CH2S-# (-~ = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 30 position of the isothiazolyl ring and Xn corresponding for each f co.. yound to a line of Table D
Table 729 35 Co~ u,-ds of the general formula I.A in which UR' iY methoxy, VRn is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa iY
isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn correspo~ g for each cv,ll~ound to a line of Table D
Table 730 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa is 45 isothiazol-3-yl, the combination of the substituent in the S
2199~22 position of the isothiazolyl ring and Xn corresponding for each c~ ound to a line of Table D
Table 731 Compounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya is -CH20-# (-# - bond to AA) and Aa is isothiazol-3-yl, the c~ h;nation of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each 10 ~o..~o~lld to a line of Table D
Table 732 Compounds of the general formula I.A in which UR' is ethoxy, VR"
15 i8 methoxy, ya is -CH20-# ( -# 2 bond to Aa) and A~ is isothiazol-3-yl, the combination of the ~ubstituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 733 C~..,~ounds of the general formula I.A in which UR' is methylamino, VRn is methoxy, ya is -CH20-# (-# = bond to A~) and Aa is isothiazol-3-yl, the comh; nation of the substituent in the S
25 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 734 30 Compounds of the general formula I.A in which UR' is ethylamino, VR~' is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each c ~nd to a line of Table D
Table 735 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methylamino, ya is -CH2O-# (-# = bond to Aa) and A~ is 40 isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
2199~22 Table 736 Compounds of the general formula I.A in which UR' i8 ethoxy, VR"
is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is S isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 737 Compounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~ is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 15 ~...poul.d to a line of Table D
Table 738 Co,..~o~l.ds of the general ~ormula I.A in which UR' is ethoxy, VRn 20 is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each ~v...pou~ld to a line of Table D
25 Table 739 Compounds of the general formula I.A in which UR~ is methyl~ ;no~
VR~' is methoxy, Y~ is -CH2O-~ (-# 2 bond to Aa) and An is pyrazol-3-yl, the combination of the substituent in the 1 30 position of the pyrazolyl ring and Xn corresponding for each ~' compound to a line of Table D
Table 740 35 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent~in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 741 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# ( ~# 3 bond to Aa) and Aa is 45 pyrazol-3-yl, the combination of the substituent in the 1 ~ 2199422 position of the pyra201yl ring and Xn corresponding for each compound to a line of Table D
Table 742 Compounds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 743 compounds of the general formula I.A in which UR' is methoxy, VRn 15 is methoxy, ya iS -CH2S~ # = bond to A~) and Aa i8 ( pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each c~i..pound to a line of Table D
20 Table 744 Compounds of the general formula I.A in which UR' is ethoxy, VR~
i8 methoxy, ya i8 -CH2S-# (-# = bond to Aa) and A~ is pyrazol-4-yl, the c~mh;n~tion of the substituent in the 1 25 position of the pyrazolyl ring and Xn corresponding for each cv...po~nd to a line of Table D
Table 745 30 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-~ 5 bond to A~) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding ~or each compound to a line of Table D
Table 746 Co,..~ou,.ds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH25-# (-# = bond to A~) and Aa is 40 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
~199122 Table 747 .
Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-# (-# = bond to Aa) and Aa iS
5 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each co..,yvund to a line of Table D
Table 748 Compounds of the general formula I.A in which UR' i8 ethoxy, VR"
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 15 c~.l,Qo~nd to a line of Table D
Table 749 Compounds of the general formula I.A in which UR' is methoxy, VR"
20 is methoxy, ya is -CH2o-$ (-# = bond to Aa) and Aa i8 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each cvmpvund to a line of Table D
25 Table 750 Co..,pounds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 30 position of the pyrazolyl ring and Xn corresponding for each ~- o~.,lpoulld to a l~ne of Table D
Table 751 35 Compounds of the general formula I.A in whi~h UR' is methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each ~vmyound to a line of Table D
Table 752 Compounds of the general formula I.A in which UR' is ethylamino, VR i5 methoxy, ya iS -CH20-# (-~ s bond to A~) and Aa is 45 pyrazol-4-yl, the combination of the substituent in the 1 ~ /4~U4 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 753 C~ o~.lds of the general form~ I.A in which UR' is methoxy, VRn is methylamino, ya i5 -CH20-# (-~ = bond to A~) and Aa i5 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 754 Cv,ll~G~nds of the general formula I.A in which UR' i8 ethoxy, VR~
15 is methylamino, Y~ is -CH20-# ~-# s bond to A~) and Aa is f pyrazol-4-yl, the combination of the substituent in the 1 ' position of the pyrazolyl ring and Xn corresponding for each cGm~ound to a line of Table D
20 Table 755 Cu.-,~oullds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -CH2S-~ = bond to Aa) and A~ i8 1,2,4-triazol-3-yl, the combination of the substituent in the 1 25 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 756 30 Compounds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is -CH2S-# (-# = bond to A~) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 757 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-~ (-# z bond to A~) and A~ is 40 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corre~ponding for each co,,.p~nd to a line of Table D
~u~U/~ 4 219~ 1 22 Table 758 C: l~unds of the general formula I.A in which UR' i5 ethylamino, VR" i8 methoxy, ya is -CH2S-~' (-# = bond to Aa) and Aa is 5 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each cG.,~o~d to a line of Table D
Table 759 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya iS -CH2S-~ = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each 15 compound to a line of Table D
'' ' ~
Table 760 Compounds of the general formula I.A in which UR' is ethoxy, VR"
20 is methylamino, ya iS -CH2S-~ bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 761 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya iS - CH20-# (-~ 3 bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 30 position of the 1,2,4-triazolyl ring and Xn corresponding for each cv...~ound to a line of Table D
Table 762 35 Co~pounds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH20-~' (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each .~...~ound to a line of Table D
Table 763 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 1,2,4-triazol-3-yl, the combinati~n of the substituent in the 1 ~19g~22 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 764 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa i8 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2~4-triazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 765 Compounds of the general formula I.A in which UR' is methoxy, VR"
lS is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the cnmh~n~tion of the substituent in the position of the 1,2,4-triazolyl ring and Xn corresponding for each cv.*oulld to a line of Table D
20 Table 766 Co...~o~..ds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 25 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table D
30 No. n R~
.~ 1 H C6H5 2 3-Cl C6H5 3 4-Cl C6H5 4 6-Cl C6H5 4-F C6Hs 6 4-OCH3 C6Hs 7 3-CH3 C6Hs 8 6-CH3 C6Hs H '3-F-C6H~
11 H 4-F-C6H~
12 H 2,3-F2-C6H3 45 13 H 2,4--F2-C6H3 14 H 2,5-F2-C6H3 lS H 2,6-F2-C6H3 ~Ju~ ~u~
2199~22 No. n R~
16 H 3,4-F2-C6H3 17 H 3,5-F2-C6H3 18 H 2-Cl-C6H4 19 H 3-Cl-C6H4 H 4-Cl-C6H4 21 3-C1 4-Cl-C6H4 22 4-C1 4-Cl-CcH4 23 6-C1 4-Cl-CcH4 24 4-F 4-Cl-CCH4 4-OCH3 4-Cl-c6H4 26 3-CH3 4-Cl-CcH4 27 6-CH3 4-Cl-CcH~
f 28 H 2,3-Cl2-C6H3 29 H 2,4-Cl2-C6H3 H 2,5-Cl2-C6H3 31 H 2,6-Cl2-C6H3 32 H 3,4-C12-C6H3 33 H 3,5-Cl2-C6H3 34 H 2,3,4-C13-C6H2 H 2,3,5-C13-C6H2 36 H 2,3,6-c13-c6H2 37 H 2,4,5-C13-C6H2 38 H 2,4,6-C13-C6H2 39 H 3,4,5-C13-C6H2 30 40 H 2-Br-C6H4 r 41 H 3-Br-CcH4 42 H 4-Br-C6H4 43 H 2,4-Br2-CcH3 44 H 2-Br, 4-F-C6H3 H 2-Br, 4-Cl-C6H3 46 H 2-F, 4-Cl-C6H
47 H 3-F, 4-Cl-C6H3 48 H 3-Cl, 5-F-C6H3 49 H 2-Cl, 4-F-C6H3 52 H 4-CN-C6H~
53 H 3-CN, 4-Cl-C6H3 0U50/452~4 219~ 122 No. n R~
H 4-H2N-C( 5S ) -C6H~
59 H 2,4-(CH3)2-C6H3 H 2,5-(CH3)2-C6H3 61 H 2,5-(CH3)2-C6H3 62 H 2,6-(CH3)2-C6H3 63 H 3,4-(CH3)2-C6H3 64 H 3,5-(CH3)2-C6H3 H 2,4,6-(CH3)3-C6H2 15 66 H 3,4,5-(CH3)3-C6H2 ( 67 H 2-CH3, 4-Cl-C6H3 68 H 2-Cl, 4-CH3-C6H3 69 H 3-CH3, 4-Cl-C6H3 20 70 H 3-Cl, 5-CH3-C6H3 71 H 2-CN, 4-CH3-C6H3 72 H 2-CH3., 4-CN-C6H3 73 H 4-(C2Hs)~C6H4 ~ 25 H 4-tC(CH3)3]-C6H~
H 3-(C6Hs)-C6H4 76 H 4-(C6H5)-C6H~
77 H 2-CF3-C6H~
30 79 H 4-CF3-C6H~
r 80 H 3,5-(CF3)2-C6H3 81 H 2-Cl, 4-CF3-C6H3 82 H 2-OCH3-C6H~
35 83 H 3-OCH3-C6H~
84 H 4-OCH3-C6H~
H 2,4-(OCH3)2-C6H3 86 H 3,4-(OCH3)2-C6H3 40 87 H 2,5-(OCH3)2-C6H3 88 H 3,5-(OCH3)2-C6H3 89 H 3,4,5-(OCH3)3-C6H2 H 2-CH3, 4-OCH3-C6H3 91 H 2-Cl, 4-OCH3-C6H3 92 H 4-OCF3-C6H~
93 H 2-0CHF2-C6H~
~U~/4~u4 203 2~ 99~122 No. n R~
H 4-ocHF2-c6H4 5 96 H 4-(OCF2CHF2)-C6H~
97 H 2-F, 4-OCHF2-C6H3 98 H 4-(OCH2CH3)-C6H4 99 H 4-tOC(CH3)3]-C6H~
100 H 3-(CO2CH3)-C6H~
101 H 4-(CO2CH3)-C6H~
102 H 4-[CO2C~CH3) 3 ] -C6H4 103 H 2,3-~O-CH2-0]-C6H3 104 H 3,4-[O-CH2-O]-C6H3 15 105 H 3~4-to-c(cH3)2-o]-c6H3 ( 106 H 3,4-[O-CH2CH2-O~-C6H3 107 H 2,3-[(CH2)~]-C6H3 108 H 3,4-[(CH2)4]-CcH3 20 109 H 2,3-(CH=CH2-CH=CH)-C6H3 110 H 3,4-(CH=CH-CH=CH)-C6H3 114 H C(CH3)2 116 H CHCH(CH3)2 117 H CH(CH3)CH2CH3 3 llô H C(CH3)3 (~ 119 H Cyclopropyl 120 H Cyclohexyl 121 H 2-Tetrahydrofuranyl 35 122 H 3-Tetrahydrofuranyl 123 H 3-Tetrahydrothienyl 124 H 2-1,3-Dioxolenyl 125 H 2-1,3-Dioxanyl 40 126 H 4-Tetrahydropyranyl 127 H Pyrid-2-yl 128 H 5-Cl-Pyrid-2-yl 129 H 5-CF3-Pyrid-2-yl 219~122 Table 767 Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is methoxy, ya is -CH=CH- and Aa is a heterocyclic 5 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 768 10 C _~oundg of the general formula I.A (n = 0) in which UR' is ethoxy, VR" is methoxy, ya is -CH=CH- and Aa i8 a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.l 15 Table 769 ~' Compounds of the general formula I.A (n - 0) in which UR' is methoxy, VR" is ethoxy, ya is -CH=CH- and A~ is a heterocyclic structure, this heterocyclic structure corresponding for each 20 compound to a line of Table D.l Table 770 Compounds of the general formula I.A (n = 0) in which UR' i8 25 ethoxy, VR" is ethoxy, ya is -CH=CH- and Aa i9 a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 771 f-- Compounds of the general formula I.A (n = 0) in which UR' is methylamino, VR" i5 methoxy, ya is -CH=CH- and Aa is a heterocyclic structure, thi~ heterocyclic structure corresponding for each c _-~und to a line of Table D.1 Table 772 Compounds o~ the general formula I.A (n = 0) in which UR' is ethylamino, VR" is methoxy, ya is -CH=CH- and Aa is a heterocyclic 40 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l 0050~45204 -Table 773 Compounds of the general formula I.A (n = 0) in which UR' is methylamino, VR" is ethoxy, ya is -CH=CH- and Aa is a heterocyclic 5 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 774 10 C~ oUnds of the general formula I.A (n = 0) in which UR' is ethylamino, VR" is ethoxy, ya iS -CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each co~ und to a line of Table D.l .
15 Table 775 f.
Compounds of the general formula I.A (n Q 0) in which UR' is methoxy, VR" is methylamino, ya is -CH=CH- and A~ is a heterocyclic structure, this heterocyclic structure corresponding 20 for each compound to a line of Table D.1 Table 776 C~ ~ounds of the general formula I.A (n - 0) in which UR' is 25 ethoxy, VRn is methylamino, ya is -CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.1 Table 777 ~-~ Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VRn is ethylamino, ya is -CH-CH- and Aa is a heterocyclic structure, thi3 heterocyclic structurQ corresponding for each compound to a line of Table D.l Table 778 Compounds of the general formula I.A (n = 0) in which UR' is ethoxy, VR" is ethylamino, ya is -CH=CH- and Aa is a heterocyclic 40 structure, thi~ heterocyclic structure corresponding for each compound to a line of Table D.1 00~0/45204 ~ 2199~22 Table D.l No. Het 5 01 1--CE~3 py~ L~)l--3--yl 02 l-CH(CB3)2 py~ ~3~y 03 1 - C (CB3)3 py~Ol~3~y 04 1-cyclo~ yl-pyrrol-3 05 l-C6H~ ~y~L~1~3~yl 06 1-(2-CB3-C6B4)-pyrrol-3-yl 07 1-(3-CB3-C6H4)-pyrrol-3-yl 08 1-(4-CH3-C6H4)-pyrrol-3-yl o9 1-(3-OCH3-CGH4) PYLrO1-3-Y1 15 10 1-(4-OCH3-C6H~)-pyrrol-3-yl 11 1-(4-N02-C6H4)-pyrrol-3-yl 12 1-(3-N02-C6B~)-pyrrol-3-yl 13 1-(4-CN-C6~4)-pyrrol-3-yl 14 1-(3-CN-C6~4) PYLL~1_3_Y1 1-(3-CF3-C6H4)-pyrrol-3-yl 16 1-(4-CF3-C6H~)-pyrrol-3-yl 17 1-(4-C(CB3)3-C6H4)-pyrrol-3-yl 18 1-(4-CCHs-C6H4) pyL ~ ol-3-yl 25 19 1--(2--Cl--C6H4) pyL~ ol--3--yl 1-(3-Cl-C6H~) ~yL~Ol~3~y 21 1-(4-Cl-C6H4) py~Ol~3~yl 22 1-(2-Br-C6H4) prLLol-3-yl 23 1-(3-Br-C6H~) prL~ol-3-yl 24 l-(4-sr-c6H4)-pyrrol-3 1-(2-F-C6H~)-pyrrol-3-yl 26 1-(3-F-C6H~)-pyrrol-3-yl 27 1-(4-F-C6B~)-pyrrol-3-yl 35 28 1-(2,4-Cl2-C6H3)-pyrrol-3-yl 29 1-(2,5-Cl2-C6B3)-pyrrol-3-yl 1-(2,6-Cl2-C6H3)-pyrrol-3-yl 31 1-(3,4-Cl2-C6H3)-pyrrol-3-yl 32 1-(2,4-F2-C6~3)-pyrrol-3-yl 40 33 1-( 2,5-F2-C6B3)-pyrrol-3-yl 34 1-( 2,6-F2-C6H3)-pyrrol-3-yl 1-(3,4-F2-C6H3) py ol-3-yl 36 1--(2-Cl, 5--ocH3-c6B3)-pyrrol--3-yl 45 37 1-( 2 - Cl, 5-CB3-C6B3)-pyrrol-3-yl 38 1-(5-Cl, 2-OCH3-C6~3)-pyrrol-3-yl 39 1-(5-Cl, 2-CB3-C6H3)-pyrrol-3-yl 00~0/45204 ~1994~2 No. Het 1-t2,5-(CH3)2-C6H3]-pyrrol-3-yl 41 1-CH3-pyrrol-2-yl 42 1-CH(CH3)l-~y~ ~2-y 43 1-C(CH3)3-pyrrol-2-yl 44 1-cyclopropyl-pyrrol-2-yl 1-C6H~ ~yL~1~2~yl 46 1-~2-CH3-CtH4) ~yLL~1~2~yl lO 47 1-(3 CB3-C6H4) ~rLLol-2-yl 48 1-(4-CH3-C6H4) PYLL~1_2_Y1 49 1-(3-OCH3-C6H4) PYL~O1-2-Y1 1-(4-OCH3-C6H~) ~yL~vl~2~yl 15 51 1-(4-NO2-C6H~) ~ylLul~2~yl f 52 1-(3-N02-CcH4) ~yLL~1~2~yl 53 1-(4-CN-C6H~) p~L ol-2-yl 54 1-(3-CN-C6H~) ~y Lol-2-yl 1-(3-CF3-C6H~) PYLSU1-2-Y1 20 56 1-(4-CF3-C6H~) PY~L~1_2_Y
57 1-(4-C(CH3)3-C6H4) ~yLLol~2~y 58 1-(4-C6H5-C6H~) PYL~V1-2-Y1 59 1-(2-C1-C6H4) ~YLL~1_2_Y1 1-(3-Cl-C6H4) ~yLLOl-2-yl 1-(4-Cl-C6H~) ~yL~1-2-yl 62 1-(2-Br-C6H4) ~yLLOl~2~y 63 i--( 3--Br--C6H4 ) e~yL~ 2--yl 64 1-(4-Br-C6H~) ~yL~ol~2~y 30 65 1-(2-F-C6H4) PYLLO1-2-Y1 f 66 1-(3-F-C6H4) PYLL~1-2_Y1 67 1-(4-F-C6H4) PYLLO1-2-Y1 68 1-(2,4-C12-C6H3) ~YLLO1_2_Y1 69 1 - ( 2,5-Cl2-C6H3)-pyrrol-2-yl 1-(2,6-C12-C6H3) ~ylLol-2-yl 71 l-(3,4-Cl2-C6H3)-pyrrol-2-yl 72 l-(2,4-F2-C6H3)-pyrrol-2-yl 73 1-(2,5-F2-C6H3)-pyrrol-2-yl 40 74 1-(2,6-F2-C6H3)-pyrrol-2-yl l-(3,4-F2-C6H3)-pyrrol-2-yl 7 6 1 - ( 2-Cl, 5-OCH3-C6H3)-pyrrol-2-yl 77 1-(2-Cl, 5-CH3-C6H3)-pyrrol-2-yl 78 1-(5-Cl, 2-OCH3-C6R3)-pyrrol-2-yl 79 1-(5-Cl, 2-CH3-C6H3)-pyrrol-2-yl 1-[2,5-(CH3)2-C6H3]-pyrrol-2-yl 2~99;1~2 No. Het 81 5-CH3-furan-2-yl 82 5-CB(CH3)2-furan-2-yl 83 5-C(CH3)3-fulan 2-yl 84 5-cyclv~r~yl-furan-2 5-C6Hs-furan-2-yl 86 5-(2-CH3-C6H4)-furan-2-yl 87 5-(3-CH3-C6H4)-furan-2-yl 10 88 5-(4-CH3-C6H4)-furan-2-yl 89 5-(3-OCH3-C6H4)-furan-2-yl 5-(4-OCH3-C6H4)-furan-2-yl 91 5-(4-N02-4H4)-furan-2-yl 15 92 5-(3-N02-C6H~)-furan-2-yl f 9 3 5-(4-CN-C6H~)-furan-2-yl 94 5-(3-CN-C6H4)-fu~ d~- 2-yl 5-(3-CF3-C6H~)-furan-2-yl 96 5-(4-CF3-C6H4)-furan-2-yl 20 97 5-(4-C(CH3)3-C6H4)-furan-2-yl 98 5-(4-C6H5-C6H4)-furan-2-yl 99 5-(2-Cl-C6H~)-furan-2-yl.
100 5-(3-Cl-C6H~)-furan-2-yl 2 101 5-(4-Cl-C6H4)-furan-2-yl 102 5-(2-~3r-C6H~)-furan-2-yl 103 5-(3-ar-c6H~) fu~dr. 2-yl 104 5-(4-Br-C6H~)-furan-2-yl 105 5-(2-F-C6H~)-furan-2-yl 30 106 5-(3-F-C6H4)-furan-2-yl 107 5-(4-F-C6H~)-furan-2-yl 108 5-(2,4-Cl2-C6H3)-furan-2-yl 109 5-(2,5-Cl2-C6H3)-furan-2-yl 110 5--(2,6-C12-C6H3)-furan--2--yl 111 5-(3,4-Cl2-C6H3)-furan-2-yl 112 5-(2,4-F2-C6H3)-furan-2-yl 113 5-(2,5-F2-C6H3)-furan-2-yl 114 5-(2,6-F2-C6H3)-furan-2-yl 40 115 5-(3,4-Fz-C6H3)-furan-2-yl 116 5-(2-Cl, 5-OCH3-C6H3)-furan-2-yl 117 5-(2-Cl, 5-CH3-C6H3)-furan-2-yl 118 5-(5-Cl, 2-OCH3-C6H3)-furan-2-yl 119 5-(5-Cl, 2-CH3-C6H3)-furan-2-yl 120 5-[2,5-(CH3)z-C6H3]-furan-2-yl 121 4-CH3-furan-2-yl 0050~452~4 2~9!~22 No. Het 122 4-CH(CH3)2-furan-2-yl 123 4-C(CH3)3-furan-2-yl 124 4-cyclG~ yl-furan-2-yl 125 4-C6Hs-furan-2-yl 126 4-(2-CH3-C6H4)-furan-2-yl 127 4-(3-CH3-C6H4)-furan-2-yl 128 4-(4-CH3-C6~4)-furan-2-yl 10 129 4-(3-OCH3-C6H4)-furan-2-yl 130 4-(4-OCH3-C6H4)-fu~an 2-yl 131 4-(4-N02-C6H4)-furan-2-yl 132 4-(3-N02-C6H4)-furan-2-yl 15 133 4-(4-CN-C6H~)-furan-2-yl 134 4-(3-CN-C6H4)-furan-2-yl -~ 135 4-(3-CF3-C6~4)-furan-2-yl 136 4-(4-CF3-C6H~)-furan-2-yl 137 4-(4-C(CH3)3-4 H4)-furan-2-yl 2~ 138 4-(4-C6H5-C6H~)-furan-2-yl 139 4-(2-Cl-C6H4)-furan-2-yl 140 4-(3-Cl-4H4)-furan-2-yl 141 4-(4-Cl-C6H4)-furan-2-yl 142 4-(2-Br-C6H~)-furan-2-yl 143 4-(3-Br-C6H~)-furan-2-yl 144 4-(4-Br-C6H4)-furan-2-yl 145 4-(2-F-C6H4)-furan-2-yl 146 4-(3-F-C6H4)-fu~ar. 2-yl 30 141 4-(4-F-C6H4)-~~-an 2-yl 148 4-(2,4-Cl2-C6H3)-furan-2-yl 149 4-(2,5-Cl2-C6H3)-furan-2-yl 150 4-(2,6-Cl2-C6H3)-furan-2-yl lS1 4-(3,4-Cl2-C6H3)-furan-2-yl 152 4-(2,4-F2-C6H3)-furan-2-yl 153 4-(2,5-F2-C6H3)-furan-2-yl 154 4-(2,6-F2-C6H3)-furan-2-yl 155 4-(3,4-F2-4H3)-furan-2-yl 40 156 4-(2-Cl, 5-OCH3-C6H3)-furan-2-yl 157 4-(2-Cl, 5-CH3-C6H3)-furan-2-yl 158 4-(5-Cl, 2-OCH3-C6H3)-furan-2-yl 159 4-(5-Cl, 2-CH3-C6H3)-furan-2-yl 160 4-[2~5-(c~3)2-c6H3]-furan-2 45 161 5-CH3-thien-2-yl 162 5-CH(CH3)2-thien-2-yl 2193~122 No. Het 163 5-C(CH3)3-thien-2-yl 164 5-cycl~p~ l-thien-2-yl 165 5-CcH5-thien-2-yl 166 5-(2-CH3-C6H4)-thien-2-yl 167 5-(3-CH3-CcH~)-thien-2-yl 168 5-(4-CH3-CcH~)-thien-2-yl 169 5-(3-OCH3-4H4)-thien-2-yl 1?0 5-(4-OCH3-C6H4)-thien-2-yl 171 5-(4-N02-C6H~)-thien-2-yl 172 5-(3-N02-CcH4)-thien-2-yl 173 5-(4-CN-CcH4)-thien-2-yl 174 5-(3-CN-CcH~)-thien-2-yl 175 5-(3-CF3-C6H~)-thien-2-yl 176 5-(4-CF3-C6H4)-thien-2-yl 177 5-(4-C(CH3)3-C6H~)-thien-2-yl 178 5-(4-C6B5-C6H4)-thien-2-yl 20 179 5-(2-Cl-C6H~)-thien-2-yl 180 5-(3-Cl-CcH4)-thien-2-yl 181 5-(4-Cl-CcH4)-thien-2-yl 182 5-(2-Br-C6~)-thien-2-yl 183 5-(3-Br-CcH4)-thien-2-yl 184 5-(.4-~r-C6H~)-thien-2-yl 185 5-(2-F-C6H4)-thien-2-yl 186 5-(3-F-C6H4)-thien-2-yl 187 5-(4-F-C6H4)-thien-2-yl 30 188 5-(2,4-Cl2-C6H3)-thien-2-yl - 189 5-(2,5-Cl2-C6H3)-thien-2-yl 190 5--(2,6-C12--C6H3)-thien--2--yl 191 5-(3,4-Cl2-C6H3)-thien-2-yl 192 5-(2,4-F2-CcH3)-thien-2-yl 193 5-(2,5-F2-CcH3)-thien-2-yl 194 5-(2,6-F2-C6H3)-thien-2-yl 195 5-(3,4-F2-CcH3)-thien-2-yl 196 5-(2-Cl, 5-OCH3-C6H3)-thien-2-yl 197 5-(2-Cl, 5-CH3-C6H3)-thien-2-yl 198 5-(5-Cl, 2-OCH3-C6H3)-thien-2-yl 199 5-(5-Cl, 2-CH3-C6H3)-thien-2-yl 200 5-[2,5-(CH3)2-C6H3]-thien-2-yl 201 4-CH3-thien-2-yl 202 4-CH(CH3)2-thien-2-yl 203 4-C(CH3)3-thien-2-yl ~ 211 2199~22 No. Het 204 4-cyclopropyl-thien-2-yl 205 4-C6H5-thien-2-yl 206 4-(2-CH3-C6H4)-thien-2-yl 207 4-(3-CH3-C6~4)-thien-2-yl 208 4-(4-CH3-C6H~)-thien-2-yl 209 4-(3-OCH3-CcH4)-thien-2-yl 210 4-(4-OCH3-C6H~)-thien-2-yl lO 211 4-(4-NO2-C6H4)-thien-2-yl 212 4-(3-NO2-C6H4)-thien-2-yl 213 4-(4-CN-C6H4)-thien-2-yl 214 4-(3-CN-C6H~)-thien-2-yl 15 215 4-(3-CF3-C6Hg)-thien-2-yl f~ 216 4-(4-CF3-C6H~)-thien-2-yl 217 4-(4-C(CH3)3-C6H~)-thien-2-yl 218 4-(4-C6H5-C6H~)-thien-2-yl 219 4-(2-Cl-C6H4)-thien-2-yl 20 220 4-(3-Cl-C6H~)-thien-2-yl 221 4-(4-Cl-C6H4)-thien-2-yl 222 4-(2-Br-C6H4)-thien-2-yl 223 4-(3-Br-C6H~)-thien-2-yl 224 4-(4-Br-C6H~)-thien-2-yl 225 4-(2-F-C6H~)-thien-2-yl 226 4-(3-F-C6H~)-thien-2-yl 227 4-~4-F-C6H4)-thien-2-yl 228 4-(2,4-Cl2-C6H3)-thien-2-yl 30 229 4-(2,5-Cl2-C6H3)-thien-2-yl ~~ 230 4-(2,6-Cl2-C6H3)-thien-2-yl 231 4-(3,4-Clz-C6H3)-thien-2-yl 232 4-(2,4-F2-4H3)-thien-2-yl 233 4-(2,5-F2-C6H3)-thien-2-yl 234 4-(2,6-F2-CcH3)-thien-2-yl 235 4-(3,4-F2-CGH3)-thien-2-yl 236 4-(2-Cl, 5-OCH3-C6H3)-thien-2-yl 237 4-(2-Cl, 5-CH3-C6H3)-thien-2-yl 40 238 4-(5-Cl, 2-OCH3-C6H3)-thien-2-yl 239 4-(5-Cl, 2-CH3-C6H3)-thien-2-yl 240 4-~2,5-(CH3)2-C6H3]-thien-2-yl 241 2-CH3-thien-4-yl 242 2-CH(CH3)2-thien-4-yl 243 2-C(CH3)3-thien-4-yl 244 2-cyclopl~pyl-thien-4-yl No. Het 245 2-C6H5-thien-4-yl 246 2-(2-CH3-C6H4)-thien-4-yl 5 247 2-(3-CH3-4 H~)-thien-4-yl 248 2-(4-CH3-C6H~)-thien-4-yl 249 2-(3-OC~3-C6H~)-thien-4-yl 250 2-(4-OCH3-C6H~)-thien-4-yl 251 2-(4-NO2-C6H4)-thien-4-yl 10 252 2-(3-NO2-C6H4)-thien-4-yl 253 2-(4-CN-C6H~)-thien-4-yl 254 2-(3-CN-C6H~)-thien-4-yl 255 2-(3-CF3-C6H4)-thien-4-yl 5 256 2-(4-CF3-C6H4)-thien-4-yl 1 257 2-(4-C(C83)3-C6H~)-thien-4-yl 258 2-(4-CGHs-Cc~)-thien-4-yl 259 2-(2-Cl-C6H~)-thien-4-yl 260 2-(3-Cl-C6H~-thien-4-yl 261 2-(4-Cl-C6H~)-thien-4-yl 262 2-(2-Br-C6H4)-thien-4-yl 263 2-(3-Br-C6H~)-thien-4-yl 264 2-(4-Br-C6H4)-thien-4-yl 265 2-(2-F-C6H~)-thien-4-yl 266 2-(3-F-C6H4)-thien-4-yl 267 2-(4-F-C6H~)-thien-4-yl 268 2-(2,4-Cl2-C6H3)-thien-4-yl 269 2-(2,5-Cl2-C6H3)-thien-4-yl 30 270 2-(2,6-Cl2-C6H3)-thien-4-yl ~- 271 2-(3,4-Cl2-C6H3)-thien-4-yl 272 2-(2,4-F2-C6H3)-thien-4-yl 273 2-(2,5-F2-C6H3)-thien-4-yl 274 2-(2,6-F2-C6H3)-thien-4-yl 275 2-(3,4-F2-C6H3)-thien-4-yl 276 2-~2-Cl, 5-OCH3-C6H3)-thien-4-yl 277 2-(2-Cl, 5-CH3-C6H3)-thien-4-yl 278 2-(5-Cl, 2-OCH3-C6H3)-thien-4-yl 40 279 2-(5-Cl, 2-CH3-C6H3)-thien-4-yl 280 2-t2,5-(CH3)2-C6H3]-thicn-4-yl 281 l-CH3-pyrazol-4-yl 282 l-CH(CH3)2-pyrazol-4-yl Z83 l-C(CH 3 )3-pyrazo1-4-yl 284 1-cyclopropyl-pyrazol-4-yl 285 l-C6H5-pyrazol-4-yl O~SU~ 4~ J4 ~ 213 2~99122 No. Het 286 1-(2-CH3-C6H4)-pyrazol-4-yl 287 1-(3-CB3-C6H4)-pyrazol-4-yl 5 288 1-(4-CH3-C6H4)-pyrazol-4-yl 289 1-(3-OCH3-C6H4)-pyrazol-4-yl 290 1-(4-OCR3-C6H~)-pyrazol-4-yl 291 1-(4-NO2-C6H~)-pyrazol-4-yl 292 1-(3-NO2-C6H~)-pyrazol-4-yl 10 293 1-(4-CN-C6H4)-pyrazol-4-yl 294 1-(3-CN-C6H4)-pyrazol-4-yl 295 1-(3-CF3-C6H4)-pyrazol-4-yl 296 1-(4-CF3-C6Hg)-pyrazol-4-yl 15 297 1-(4-c(cH3)3-c6H~)-pyrazol-4 298 1-(4-C6H5-CcH~)-pyrazol-4-yl 299 1-(2-Cl-C6H4)-pyrazol-4-yl 300 1-(3-Cl-C6H~)-pyrazol-4-y 301 1-(4-Cl-C6H4)-pyrazol-4-yl 20 302 1-(2-Br-C6H~)-pyrazol-4-yl 303 1-(3-Br-4H~)-pyrazol-4-yl 304 l-(4-Br-C6H4)-pyrazol-4-yl 305 1-(2-F-C6H4)-pyrazol-4-yl 306 1-(3-F-C6H~)-pyrazol-4-yl 307 1-(4-F-C6H~)-pyrazol-4-yl 308 1-(2,4-C12-C6H3)-pyrazol-4-yl 309 1-(2,5-C12-C6H3)-pyrazol-4-yl 230 1-(2,6-C12-C6R3)-pyrazol-4-yl 30 311 1-(3,4-C12-C6H3)-pyrazol-4-yl f 312 l-(2,4-F2-C6~3)-pyrazol-4-yl 313 l-(2,5-F2-C6H3)-pyrazol-4-yl 314 1-(2,6-F2-C6H3)-pyrazol-4-yl 315 l-(3,4-F2-CcH3)-pyrazol-4-yl 316 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 311 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 318 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 319 1-(5-Cl, 2-CH3-C6H3)-pyrazol-4-yl 40 320 l-t2~5-(cH3)2-c6H3]-pyrazol-4 321 1,5-(CH3)2-pyrazol-3-yl 322 1-CH3, 5-CH(CH3)2-pyrazol-3-yl 323 1-CH3, 5-C(CH3)3-pyrazol-3-yl 324 1-CH3, 5-cyclopLv~yl-pyrazol-3 325 l-CH3, 5-C6H5-pyrazol-3-yl 326 1-CH3, 5-(2-CH3-C6H4)-pyrazol-3-yl ~ 214 2199122 No. Het 327 1-CH3, 5-(3-CB3-C6H4)-pyrazol-3-yl 328 1-CH3, 5-(4-CH3-C6H4)-pyrazol-3-yl 5 329 1-CH3, 5-(3-OCH3-C6H4)-pyrazol-3-yl 330 1-CH3, 5-(4-OCH3-C6H4)-pyrazol-3-yl 331 1-CH3, 5-(4-N02-C6H4)-pyrazol-3-yl 332 1-CH3, 5-(3-N02-C6H4)-pyrazol-3-yl 333 1-CH3, 5-(4-CN-C6H4)-pyrazol-3-yl 0 334 1-CH3, 5-(3-CN-C6H~)-pyrazol-3-yl 335 1-CH3, 5-(3-CF3-C6H4)-pyrazol-3-yl 336 l-CH3, 5-(4-CF3-C6H4)-pyrazol-3-yl 337 1-CB3, 5-(4-C(CH3)3-C6H4)-pyrazol-3-yl 15 338 1-CH3, 5-(4-CcH5-C6H~)-pyrazol-3-yl 339 1-CH3, 5-(2-Cl-C6H~)-pyrazol-3-yl 340 1-CH3, 5-(3-Cl-C6H~)-pyrazol-3-yl 341 1-CH3, 5-(4-Cl-C6~)-pyrazol-3-yl 342 1-CH3, 5-(2-Br-C6H~)-pyrazol-3-yl 20 343 1-CH3, 5-(3-~r-4H~)-pyrazol-3-yl 344 1-CH3, 5-(4-Br-C6H4)-pyrazol-3-yl 345 1-CH3, 5-(2-F-C6H4)-pyrazol-3-yl 346 1-CH3, 5-(3-F-C6H~)-pyrazol-3-yl 2 347 1-CH3, 5-(4-F-C6H4)-pyrazol-3-yl 348 1-c~3, 5-(2,4-C12-C6~3)-pyrazol-3-yl 349 1-CH3, 5-(2,5-Cl2-C6H3)-pyrazol-3-yl 350 1-CH3, 5-(2,6-C12-C6H3)-pyrazol-3-yl 351 l-CH3, 5-(3,4-C12-C6H3)-pyrazol-3-yl 30 352 1-CH3, 5-(2,4-F2-C6H3)-pyrazol-3-yl ~~-~ 353 1-CH3, 5-(2,5-F2-C6H3)-pyra201-3-yl 354 1-CH3, 5-(2,6-F2-C6H3)-pyrazol-3-yl 355 1-CH3, 5-(3,4-F2-C6H3)-pyrazol-3-yl 356 1-CH3, 5-(2-Cl, 5-OCH3-C6H3)-pyrazol-3-yl 357 1-CH3, 5-(2-Cl, 5-CH3-C6H 3 ) - pyrazol-3-yl 358 1-CH3, 5-(5-Cl, 2-OCH3-C6~3)-pyrazol-3-yl 359 1-CH3, 5-(5-Cl, 2-CH3-C6H3)-pyrazol-3-yl 360 1-CH3, 5-t2,5-(CH3)2-C6H3~-pyrazol-3-yl 40 361 3-CH3-;~o~zol-5-yl 362 3-CH(C~3)2-;Ro~701-5-yl 363 3-C(CH3)3-isoxazol-5-yl 364 3-cyclop~opyl-iQoxazol-5-yl 365 3-C6Hs-iRoxazol-5-yl 366 3-(2-CH3-C6H4)-; ROy~ 701 - 5-yl 367 3-(3-CH3-C6H4)-iQ~7ol-5-yl No. Het 368 3-(4-CH3-C6H~)-isoxazol-5-yl 369 3-(3-OCH3-C6H4)-i~nY~zol-5 5 370 3-(4-OCH3-C6~4)-isoxazol-5-yl 371 3-(4-N02-C6H~ qoY~7-01-5-yl 372 3-(3-No2-c6B4)-;~yA 701-5-yl 373 3-(4-CN-C6H4)-isoxazol-S-yl 374 3-(3-CN-C6H4)-isoxazol-5-yl 10 375 3-(3-CF3-C6H4)-i~oYA701-5-yl 376 3-(4-CF3-C6B~ oYA7ol-5 377 3-(4-C(CH3)3-C6H4)-i80YAzol-5 378 3-(4-C6H5-C6H4)-isoxazol-5-yl 379 3-(2-Cl-C6~4)-isoxazol-5-yl f 380 3-(3-Cl-C6~ oY~701-5-yl 381 3-(4-Cl-C6H4)-;~YA701-5-yl 382 3-(2-Br-C6H4)-;Qo~701-5-yl 383 3-(3-Br-C6H4)-isoxazol-5-yl 20 384 3-(4-Br-C6H4)-isoxazol-5-yl 385 3-(2-F-C6~ OYA701-5-Y1 386 3-(3-F-C6H~)-isoxazol-5-yl 387 3-(4-F-C6H4)-;~oY~701-5-yl 388 3-(2,4-C12-CcH3)-isoxazol-5-yl 389 3-(2,5-Cl2-C6H3)-isoxazol-5-yl 390 3-(2,6-C12-C6H3)-isoxazol-5-yl 391 3-(3,4-Cl2-C6~3)-;~Y~701-5-yl 392 3-(2,4-F2-C6H3)-;R~Y~701-5-yl 30 393 3-(2,5-F2-CGH3)-isoxa201-5-yl ~~~ 394 3-(2,6-F2-CcH3)-;~Y~7ol-5-yl 395 3-(3,4-F2-CcH3)-isoxazol-5-yl 396 3-(2-Cl, 5-OCH3-CcH3)-;~oY~zol-5-yl 397 3-(2-Cl, 5-CH3-C6H3)-i~oxazol-5-yl 398 3-(5-Cl, 2-OCH3-CcH3)-isoxazol-5-yl 399 3-(5-Cl, 2-CH3-C6H3)-iQoYA7ol-5 400 3-~2,5-(CH3)2-C6H3]-;noYA701-5-yl 401 3-CH3-4-Cl-isoxazol-5-yl 40 402 3-CH(C~3)2-4-Cl-~OYA701-5-yl 403 3-C(CH3)3-4-Cl-isoxazol-5-yl 404 3-cycl~ yl-4-cl-;~Y~7ol-5 405 3-C6H5-4-Cl-isoxazol-5-yl 406 3-(2-CH3-C6H4)-4-Cl-isoxazol-5-yl 407 3-(3-C~3-C6~)-4-Cl-;~oY~7~1-5-yl 408 3-(4-CH3-C6~4)-4-Cl-isoxazol-5-yl .
No. Het 409 3-(3-OC~3-CGH~)-4-C~ oxazol-5-y 410 3-(4-OCH3-C6H4)-4-Cl-isoxazol-5-yl 5 411 3-(4-NOz-CGH4)-4-Cl-isoxazol-5-yl 412 3-(3-N02-CGH4)-4-Cl-isoxazol-5-yl 413 3-(4-CN-CGH4)-4-Cl-iQ~YA7Ql-5-yl 414 3-(3-CN-CGH4)-4-Cl-;Q~YA7-ol-5-yl 415 3-(3-CF3-C6H~)-4-Cl-;-~oY~701-5-yl 10 416 3-(4-CF3-CGH41-4-Cl-~oY~7ol-5-yl 417 3-(4-C(CH3)3-C6H4)-4-cl-;QQYa~tQl-5-y 418 3-(4-CGH5-C6H4)-4-Cl-isoxazol-5-yl 419 3-(2-Cl-CGH4)-4-Cl-;soYA7ol-5-yl 420 3-(3-Cl-CGH~)-4-Cl-;Q~Y~7ol-5-yl ! 421 3-(4-Cl-C6H4)-4-Cl-;s~Y~ol-5-yl 422 3-(2-~r-C6H~)-4-Cl-isoxazol-5-yl 423 3-(3-Br-4H~)-4-Cl-~QoYa~Ql-5-yl 424 3-(4-Br-C6H~)-4-C~ oYAzol-5-yl 20 425 3-(2-F-C6H~)-4-Cl-isoxazol-S-yl 426 3-(3-F-CGH4)-4-Cl-isoxazol-5-yl 427 3-(4-F-C6H4)-4-Cl-iQoY~701-S-yl 428 3-(2~4-C12-CGH3)-4-Cl-isoxazol-5-yl 429 3-(2,5-C12-CG~3)-4-C1-;QOY~701-5-Y1 430 3-(2,6-C12-CGH3)-4-Cl-;QoY~Ql-5-yl 431 3-(3,4-C12-CGH3)-4-Cl-~QoYA~Ql-5-yl 432 3-(2,4-F2-C6H3)-4-Cl-;PoY~7Ql-5-yl 433 3-(2,5-F2-C6H3)-4-Cl-;R~Y~701-5-yl 30 434 3-(2,6-F2-C6H3)-4-Cl-;QoY~701-S-yl 435 3-(3,4-F2-C6H3)-4-Cl-iQn~7ol-5-yl 436 3-(2-Cl, 5-OCH3-C6H3)-4-Cl-i~oxazol-5-y 437 3-(2-Cl, 5-C~3-C6H3)-4-Cl-iQoY~7ol-5 438 3-(5-Cl, 2-OCH3-C6H3)-4-Cl-iQoYA~ol-5 439 3-(5-Cl, 2-CH3-C6H3)-4-Cl-isoxazol-5-yl 440 3~t2,5~(CH3)z-C6H3]-4-Cl-isoxazol-5-yl 441 5-CH3-isoxazol-3-yl 442 5-CH(CH3)2-isoxazol-3-yl 40 443 5-C(CH3)3-;QoY~701-3-yl 444 5-cycl~ ~l-iQ~701-3-yl 445 5-CGHs-isoxazol-3-yl 446 5-(2-CH3-CcH4)-isoxazol-3-yl 447 5-(3-CH3-C6H4)-isoxazol-3-yl 448 5-(4-CH3-CGH4)-isoxazol-3-yl 449 5-(3-OCB3-C6H~)-isoxazol-3-yl .
uv~
~ 217 21~9 i22 No. Het 450 5-(4-OCH3-C6H~ QoY~zol-3-yl 451 5-(4-N02-C6H4)-iQoxazol-3-yl 452 5-(3-N02-C6H4)-isoxazol-3-yl 453 5-(4-CN-C6~4)-isoxazol-3-yl 454 5-(3-CN-C6H4)-isoxazol-3-yl 455 5-(3-CF3-C6H~)-isoxazol-3-yl 456 5-(4-CF3-C6H~)-isoxazol-3-yl 457 5-(4-C(CH3)3-C6H4)-isoxazol-3-yl 458 5-(4-C6H5-C6~)-isoxazol-3-yl 459 5-(2-CI-C6H4)-i30xazol-3-yl 460 5-(3-Cl-C6H4)-isoxazol-3-yl 15 461 5-(4-Cl-C6H4)-;Qo~7~1-3-yl ! 462 5-(2-Br-C6H4)-;~Y~ol-3-yl 463 5-(3-Br-C6B4)-isoxazol-3-yl 464 5-(4-Br-C6H4)-;-8 n~ 701 -3-yl 465 5-(2-F-C6H~)-;QOY~Q1-3-Y1 ~ 20 466 5-(3-F-C6H4)-isoxazol-3-yl 467 5-(4-F-C6H~)-isoxazol-3-yl 468 5-(2,4-Cl2-C6H3)-~sx~70l-3-yl 469 5-(2,5-Cl2-C6H3)-isoxazol-3-yl 2 470 5-(2,6-C12-C6H3)-i~oxazol-3-yl 471 5-(3,4-Cl2-C6H3)-isoxazol-3-yl 472 5-(2,4-F2-C6H3)-isoxazol-3-yl 473 5-(2,5-F2-C6H3)-i QQY~ 7Ql - 3 - yl 474 5-(2,6-F2-C6H3)-isoxazol-3-yl 30 475 5-(3,4-F2-C6R3)-isoxazol-3-yl ~- 476 5-(2-Cl, 5-OCH3-C6H3)-; QOY~ 701-3-yl 477 5-(2-Cl, 5-CH3-C6H3)-i30xazol-3-yl 478 5-(5-Cl, 2-OCH3-C6H3)-i~Q~Y~zQl-3 ~ 479 5-(5-Cl, 2-CH3-C6H3)-isoxazol-3-yl 480 5-[2~5-(CH3)2-C6H3~-;QoY~7-01-3-yl 481 3-CH3-isothiazol-5-yl 482 3-CH(CH3)2-isothiazol-5-yl 483 3-C(CH3)3-isothiazol-5-yl 40 484 3-cyclo~ l-i80th;~ol-5-yl 485 3-C6H5-i~30thiazol-5-yl 486 3-(2-CH3-C6H~)-isothiazol-5-yl 487 3-(3-CH3-C6H4)-isothiazol-5-yl 488 3-(4-CH3-C6H~)-isothiazol-5-yl 489 3-(3-OCH3-C6H4)-i~othiazol-5-yl 490 3-(4-OCH3-C6H4)-isothiazol-5-yl 218 2199~
No. Het 491 3-(4-N02-C6H~)-isothiazol-5-yl 492 3-(3-N02-C6~ othiazol-5-yl 493 3-(4-CN-C6H4)-isothiazol-5-yl 494 3-(3-CN-C6H4)-isothiazol-5-yl 495 3-(3-CF3-C6H4)-isothiazol-5-yl 496 3-(4-CF3-CcH4)-isothiazol-5-yl 497 3-(4-C(CB3)3-C6B~)-isothiazol-5-yl 10 498 3-(4-C6H5-C6H4)-isothiazol-5-yl 499 3-(2-Cl-C6H~)-isothiazol-5-yl 500 3-(3-Cl-C6H4)-i~othiazol-5-yl 501 3-(4-Cl-C6B4)-isothiazol-5-yl 15 502 3-(2-Br-C6H4)-isothiazol-5-yl ~ 503 3-(3-Br-C6B~)-isothiazol-5-yl ( 504 3-(4-Br-C6H4)-isothiazol-5-yl 505 3-(2-F-C6H4)-isothiazol-5-yl 506 3-(3-F-C6H~)-isothiazol-5-yl 20 507 3-(4-F-C6H~)-isothiazol-5-yl 508 3-(2,4-Cl2-C6B3)-isothiazol-5-yl 509 3-(2,5-Cl2-C6H3)-isothiazoL-5-yl 510 3-(2,6-Cl2-C6H3)-isothiazol-5-yl 511 3-(3,4-Cl2-C6H3)-isothiazol-5-yl 512 3-(2,4-F2-C6B3)-isothiazol-5-yl 513 3-(2,5-F2-C6R3)-isothiazol-5-yl 514 3-(2,6-F2-C6B3)-isothiazol-5-yl 515 3-(3,4-F2-C6B3)-isothiazol-5-yl 30 516 3-(2-Cl, 5-oCR3-C6H3)-isot h; ~ 70 1 - 5-yl ,_ 517 3-(2-Cl, 5-CB3-C6B3)-isothiazol-5-yl 518 3-(5-Cl, 2-OC83-C6H3)-isothiazol-5-yl 519 3-(5-Cl, 2-CH3-C6H3)-isothiazol-5-yl 520 3-t2,5-(CB3)2-C6H3]-isothiazol-5-yl 521 2-CH3-oxazol-4-yl 522 2-CB(CH3)2-oxazol-4-yl 523 2-C(CH3)3-oxazol-4-yl 524 2-cyclv~ yl-oxazol-4-yl 40 525 2-C6H5-oxazol-4-yl 526 2-(2-CH3-C6H4)-oxazol-4-yl 527 2-(3-CH3-C6H~)-oxazol-4-yl 528 2-(4-CH3-C6H4)-oxazol-4-yl 529 2-(3-OCH3-C6H~)-oxazol-4-yl 530 2-(4-OCH3-C6H~)-oxazol-4-yl 531 2-(4-N02-C6H~)-oxazol-4-yl ~99~22 No. Het 532 2-(3-NO2-CcH4)-oxazol-4-yl 533 2-(4-CN-C6H~)-oxazol-4-yl 5 534 2-(3-CN-C6H4)-oxazol-4-yl 535 2-(3-CF3-C6H4)-oxazol-4-yl 536 2-(4-CF3-C6H4)-oxazol-4-yl 537 2-(4-C(CH3)3-C6H~)-oxazol-4-yl 538 2-(4-C6Hs-C6H~)-oxazol-4-yl 10 539 2-(2-Cl-C6H4)-oxazol-4-yl 540 2-(3-Cl-C6H~)-oxazol-4-yl 541 2-(4-C~-C6H4)-oxazol-4-yl 542 2-(2-Br-C6H~)-oxazol-4-yl 543 2-(3-Br-C6H4)-oxazol-4-yl 2--(4-Br-C6H4)-oxazol--4--yl 545 2-(2-F-C6B 4 ) - oxazol-4-yl 546 2-(3-F-C6H4)-oxazol-4-yl 547 2-(4-F-C6H~)-oxazol-4-yl 20 548 2-(2,4-cl2-c6~3)-oxazol-4-yl 549 2-(2,5-Cl2-C6R3)-oxazol-4-yl 550 2-(2,6-Cl2-C6H3)-oxazol-4-yl 551 2-(3,4-C12-C6H3)-oxazol-4-yl 2 552 2-(2,4-F2-C6H3)-oxazol-4-yl 553 2-(2,5-F2-C6H3)-oxazol-4-yl 554 2-(2,6-F2-C6H3)-oxazol-4-yl 555 2-(3,4-F2-CcH3)-oxazol-4-yl 556 2-(2-Cl, 5-OCH3-C6H3)-oxazol-4-yl 30 557 2-(2-Cl, 5-CH3-C6H3)-oxazol-4-yl 558 2-(5-Cl, 2-OCH3-CcH3)-oxazol-4-yl 559 2-(5-Cl, 2-CH3-C6H3)-oxazol-4-yl 560 2-t2,5-(CH3)2-CcH3l-oxazol-4-yl 561 2-CH3-thiazol-4-yl 562 2-CH(CH3)2-thiazol-4-yl 563 2-C(CH3)3-thiazol-4-yl 564 2-cyclo~ ~yl-thiazol-4 565 2-CcH5-thiazol-4-yl 40 566 2-(2-CH3-CcH4)-thiazol-4-yl 567 2-(3-CH3-CcH~)-thiazol-4-yl 568 2-(4-CH3-CcH~)-thiazol-4-yl 569 2-(3-OCH3-CcH4)-thiazol-4-yl 570 2-(4-OCH3-CcH4)-thiazo1-4-yl 571 2-(4-NO2-C6H4)-thiazol-4-yl 572 2-(3-NO2-CcH4)-thiazol-4-yl .
00~0/45204 ~ 2199 122 No. Het 573 2-(4-CN-C6H4)-th~ ~701 -4-yl 574 2-(3-CN-C6H~)-th; ~701 -4-yl 575 2-(3-CF3-C6H4)-thiazol-4-yl 576 2-(4-CF3-C6H4)-thiazol-4-yl 577 2-(4-C(CH3)3-C6H4)-thiazol-4-yl 578 2-(4-C6H5-C6H4)-thiazol-4-yl 579 2-(2-Cl-C6H4)-thiazol-4-yl 580 2-(3-Cl-C6H4)-thiazol-4-yl 581 2-(4-Cl-CcH4)-thiazol-4-yl 582 2-(2-Br-C6~4)-thiazol-4-yl 583 2-(3-Br-C6H4)-thiazol-4-yl 584 2-(4-Br-C6H~)-thiazol-4-yl 585 2-(2-F-C6H~)-thiazol-4-yl 586 2-(3-F-C6H~)-thiazol-4-yl 587 2-(4-F-C6H~)-thiazol-4-yl 588 2-(2,4-C12-C6H3)-thiazol-4-yl 589 2-(2,5-C12-C6H3)-thiazol-4-yl 590 2-(2,6-C12-C6H3)-~h; ~701 - 4-yl 591 2-(3,4-C12-CcH3)-thiazol-4-yl 592 2-(2,4-F2-C6H3)-thiazol-4-yl 593 2-(2,5-F2-CcB3)-thiazol-4-yl 594 2-(2,6-F2-C6H3)-thiazol-4-yl 595 2-(3,4-F2-C6H3)-thiazol-4-yl 596 2-(2-Cl, 5-OCH3-C6H3)-thiazol-4-yl 597 2-(2-Cl, 5-CH3-C6H3)-thiazo1-4-yl 30 598 2-(5-Cl, 2-OCH3-C6H3)-thiazol-4-yl 599 2-(5-Cl, 2-CH3-C6H3)-thiazol-4-yl 600 2-~2,5-(CH3)2-C6H3]-thiazol-4-yl 601 1,3-(CH3)2-1,2,4-triazol-5-yl 602 1-CH3, 3-CH( CH3 ) 2 - 1, 2,4-triazol-5-yl 603 l-CH3, 3-C(CH3)3-1,2,4-triazol-5-yl 604 l-CH3, 3-cyclopropyl-1,2,4-triazol-5-yl 605 1-CH3, 3-C6Hs-1,2,4-triazol-5-yl 606 1-CH3, 3-(2-CH3-C6H~)-1,2,4-triazol-5-yl 607 l-CH3, 3-(3-CB3-CcH~)-1,2,4-triazol-5-yl 608 1-CH3, 3-(4-CH3-C6H~)-1,2,4-triazol-5-yl 609 1-CH3, 3-(3-OCH3-C6H4)-1,2,4-triazol-5-yl 610 1-CH3, 3-(4-OC~3-C6H4)-1,2,4-triazol-5-yl 611 l-CH3, 3-(4-NO2-C6H4)-1,2,4-triazol-5-yl 612 1-CH3, 3-(3-NO2-C6H~)-1,2,4-triazol-5-yl 613 l-CH3, 3-(4-CN-C6H~)-1,2,4-triazol-5-yl 2199~22 No. ~et 614 1-CH3, 3-~3-CN-C6H4)-1,2,4-triazol-5-yl 615 1-CH3, 3-(3-CF3-C6H~)-1,2,4-triazol-5-yl 616 1-CB3, 3-(4-CF3-C6~4)-1,2,4-triazol-S-yl 617 1-CH3, 3-(4-C(C~3)3-C6H4)-1,2,4-triazol-5-yl 618 1-CH3, 3-(4-C6H5-C6H4)-1,2,4-triazol-5-yl 619 1-Ca3, 3-(2-Cl-C6H4)-1,2,4-triazol-5-yl 620 1-CH3, 3-(3-Cl-C6H4)-1,2,4-triazol-S-y 10 621 1-CH3, 3-(4-Cl-C6H4)-1,2,4-triazol-5-yl 622 1-CH3, 3-(2-Br-C6B~)-1,2,4-triazol-S-yl 623 1-CH3, 3-(3-Br-C6H~)-1,2,4-triazol-5-yl 624 1-CH3, 3-(4-Br-C6~)-1,2,4-triazol-S-y 625 1-CH3, 3-(2-F-C6~4)-1,2,4-triazol-S-yl 1-CR3, 3-(3-F-C684)-1,2,4-triazol-S-yl 627 1-CH3, 3-(4-F-C6H4)-1,2,4-triazol-S-yl 628 1-CH3, 3-(2,4-C12-C6H3)-1,2,4-triazol-5-yl 629 1-CH3, 3-(2,5-C12-C6H3)-1,2,4-triazol-S-yl 20 630 1-C83, 3-(2,6-C12-C6H3)-1,2,4-triazol-S-yl 631 1-CH3, 3-(3,4-C12-C6H3)-1,2,4-triazol-5-yl 632 1-CH3, 3-(2,4-F2-C6H3)-1,2,4-triazol-S-yl 633 1-CH3, 3-(2,5-F2-C6H3)-1,2,4-triazol-5-yl 634 1-CH3, 3-(2,6-F2-C6H3)-1,2,4-triazol-5-yl 635 1-CH3, 3-(3,4-F2-C6H3)-1,2,4-triazol-5-yl 636 1-CH3, 3-(2-Cl, 5-OCH3-C6H3)-1,2,4-triazol-S-yl 637 1-CH3, 3-(2-Cl, 5-CH3-C6H3)-1,2,4-triazol-5-yl 638 1-CH3, 3-(S-Cl, 2-OCH3-C6B3)-1,2,4-triazol-5-yl 30 639 1-CH3, 3-(5-Cl, 2-CH3-C6H3)-1,2,4-triazol-5-yl 640 1-CH3, 3-~2,5-(CH3)2-C6H3]-1,2,4-triazol-S-yl 641 5-CH3-1,3,4-QYA~;A7ol-2-yl 642 5-CH(C~3)2-1,3,4-oYA~;A7Ql-2-yl 643 5-C(CH3)3-1,3,4-o~A~;A7ol-2-yl 644 5-cyclo~L~1-1,3,4-nY~;A7ol-2 yl 645 5-C6H5-1,3,4-oY~ 7.ol-2-yl 646 5-(2-CH3-C6H4)-1,3,4-oYA~;A7ol-2-yl 647 5-(3-C~3-C6H4)-1,3,4-nYA~;A7ol-2-yl 40 648 5-(4-CB3-C6H4)-1,3,4-oYA~;A7ol-2-yl 649 5-(3-OCH3-C6H4)-1~3,4-~YA~iA7ol-2-yl 650 5-(4-OCH3-C6H4)-1,3,4-nYA~;A7ol-2-yl 651 5-(4-N02-C6H4)-1,3,4-oYA~;A~Ql-2-yl 652 5-(3-N02-C6H4)-1,3,4-QYA~; A 7Ql-2-yl 653 5-(4-CN-C6~4)-1,3,4-oYA~;A7-ol 2 yl 654 5 (3 CN-C6~4) 1,3,4 ~yA~;A~Ql 2 yl .
2199 1~2 No. 8e~
655 5-(3-CF3-C6H4)-1,3,4-oYA~; A ~701-2-yl 656 5-~4-CF3-C~H~)-1,3,4-n~;A 701- 2-yl 657 5-(4-c(cH3)3-c6H4)-l~ 3~4-nY~;A701-2-658 5-(4-C6Hs-C6~)-1,3,4-oYA~i~7Ol-2-yl 659 5-(2-C1-C6H4)-1,3,4-O~Y~;A7Q1-2-Y1 660 5-(3-Cl-C6H4)-1,3,4 ~yA~;A7ol 2 yl 661 5-(4-Cl-C6H4)-1,3,4-nYA~;A 7-ol- 2-yl 0 662 5-(2-Br-C6~4)-1,3,4-oYAd;A7ol-2-yl 663 5-(3-Br-CcH4)-1,3,4-~YA~A.7Ol-2-y 664 5-(4-B~-ccH4)-lr3r4-~yA~;A7Ql-2 665 5-(2-F-C6H~)-1,3,4-oY~; A701- 2-yl 15 666 5-(3-F-C6H4)-1,3,4-o~A~iA7Ql-2-yl 667 5-(4-F-C6H~)-1,3,4-o~; A701-2-yl 668 5-( 2,4-C12-C6H3)-1, 3~4-oYA~;A7ol-2-yl 669 5-( 2r 5-C12-C6H3)-1,3,4-nY~;A 701- 2-yl 670 5-( 2r 6-C12-C6H3)-1,3,4-nYA~; A701- 2-yl 20 671 5-(3,4-C12-C6H3)-1,3,4-ox~A;A 701-2-yl 672 5-(2,4-F2-C6H3)-1,3,4-nYA~;A7ol-2-yl 673 5-(2,5-F2-C6H3)-1, 3, 4-oY~; A ~ol-2-yl 674 5-(2,6-F2-C6H3)-1,3,4-nYA~;A7Ol-2-yl 675 5-(3,4-F2-C6H3)-1,3 r 4 - oYA~ ~701-2-yl 676 5-( 2-C1~ 5-OCH3-C6H3)-1~ 3,4-oY~A7ol-2-yl 677 5-(2-Cl, 5-CH3-C6H3)-1,3,4-oYA~;A7ol-2-yl 678 5-(5-Cl, 2-OCH3-C6H3)-l, 3r4-oYA~i~Ql-2 679 5-(5-Cl, 2-CH3-C6H3)-1,3,4-QYA.~;A 701- 2-yl 30 680 5-[2,5-(CH3)2-C6H3]-1,3,4-o,Y,~;A7ol-2-yl 681 5-CH3-1,2,4- O~A~;A701- 3-yl 682 5-CH(CH3)2-1,2,4-~Y~; A701- 3-yl 683 5-C(CH3)3-1,2,4-oYa~A7ol-3-yl 684 5-cyclopropyl-1,2,4-ox,~;A7ol-3-yl 685 5-C6Hs-1,2,4-nxAA;A 7-ol-3-yl 686 5-(2-CH3-C6Hq)-1,2,4-nY~;A7ol-3-yl 687 5-(3-CH3-C6H4)-1,2,4-~A~;A7ol-3-yl 688 5-(4-CH3-C6H~)-1,2,4-nY~ 7Ql-3-yl 40 689 5-(3-OCH3-CCH4)-1,2,4-oyA~;~7ol-3-yl 690 5-(4-OCH3-CcH4)-1,2,4-nYA~;A7ol-3-yl 691 5-(4-NO2-CCH4)-l, 2~ 4-o,YA~;A7ol-3-yl 692 5-(3-NO2-C6H4)-1,2,4-oY~;A7ol-3-yl 693 5-(4-CN-C6H4)-1,2,4-oY~;A7ol-3-yl 694 5-(3-CN-C6H4)-1,2,4-oxadiazol-3-yl 695 5-(3-CF3-C6H4)-1,2,4-oYA~i~7ol-3-yl =~_ 2 1 9 9ll 2 2 No. ~et 696 5-(4-CF3-C6~4)-1,2,4-~Y~;A701-3-y 697 5-(4-C(C~3)3-C6H4)-1,2,4-~Ya~;AZol-3 5 698 5-(4-C6Hs-C6H4)-1,2~4-oYAA;A~ol-3 699 5-(2-C1-C6H4)-1,2,4-OYA~;A7Q1-3-Y1 700 5--(3--Cl--C6H4)--1~2~4--oyA~l;a7ol--3--yl 701 5_(4_C1_C6H4)_1,2,4_0~;A 701 - 3-yl 702 5-(2-Br-C6~4)-1,2,4-oY4~;A7Ql-3-y 10 703 5-(3-~r-C6R4)-1,2,4-n~;Azol-3-yl 704 5-(4-Br-CcH4)-1,2,4-oYA~; A zQl-3-yl 705 5-(2-F-C6~4)-1,2,4-~Y4A;A7ol-3 706 5-(3-F-C6B4)-1,2,4-oY~;A7ol-3-y 15 707 5-(4-F-C6H~)-1,2,4-oYaA;A7ol-3 708 5-(2~4-cl2-c6H3)-l~2~4-~Ya~;A~Ql-3 709 5-(2,5-C12-C6H3)-1,2,4-o~a~ A 701-3-yl 710 5-(2,6-C12-C6H3)-1,2,4-OY~;A7O1-3-Y1 711 5-(3,4-C12-C6H3)-1,2,4-oxadiazol-3-y 20 712 5-(2,4-F2-C6H3)-1,2,4-~YA~; A701 - 3-yl 713 5-(2,5-F2-C6H3)-1,2,4-~YA~;A7ol-3-y 714 5-(2,6-F2-C6H3)-1,2,4-oYa~a7ol-3-y 715 5-(3,4-F2-C6H3)-1,2,4-~Y4~a7ol-3-y 2 716 5-(2-Cl, 5-OCH3-C6H3)-1,2,4-~Y~;A7ol-3-y 717 5-~2-Cl, 5-CH3-C6H3)-1,2,4-~YA~; A 701-3-yl 718 5-(5-Cl, 2-OCH3-C6~3)-1,2,4-~Y~;A701-3-yl 719 5-~5-Cl, 2-C~3-C6H3)-1,2,4-oY4~;A7o1-3-yl 720 5-t2,5-(C~3)2-C6H3~-1,2,4-oY~;A7ol-3-yl 30 721 3-CH3-1,2,4-~Y~la7ol-5-y 722 3-cH(cH3)2-l~2~4-oy~n7Ql-5 723 3-C(CH3)3-1,2,4-oYA~;A~Ql-5-yl 724 3-cyclG~ l-1,2,4-oY~;A7Ql-5-yl 725 3-C6H5-1,2,4-oY4~;A 701 - 5 - yl 726 3-(2-CH3-CcH4)-1,2,4-oYa~;A?ol-5-yl 727 3-(3-CH3-C6H4)-1,2,4-oY~ 701 - 5-yl 728 3-(4-CH3-C6H4)-1,2,4-oYA~;A7ol-5 729 3-(3-ocH3-c6H4)-l~2~4-~YA~;A7Q
40 730 3-(4-OCH3-C6H~)-1,2,4-nYa~;A7ol-5-y 731 3-(4-N02-C6Hg)-1,2,4-ox~iA7ol-5-yl 732 3_(3_NO2_C6~4)_1,2,4_0Y~;A~701_5_Y1 733 3-(4-CN-4 H~)-1,2,4-~Ya~;4.7ol-5-yl 734 3-(3-CN-C6H4)-1,2,4-~Y~;~7ol-5-yl 735 3-(3-CF3-C6H4)-1,2,4-oxadiazol-5-yl 736 3-(4-CF3-C6H4)-1,2,4-oYA~;Azol-5-yl 2199~22 No. Het 737 3-(4 C(cH3)3-c6H4)-l~2~4-~yA~7ol-5 738 3-(4-c6H5-c6H4)-l~2~4-oAy~ A~ ol-5-yl 739 3-(2-Cl-C6Hq)-1,2,4-oY~;A7ol-5-yl 740 3-(3-Cl-C6H4)-1,2,4-oY. A~; A70l-5-yl 741 3-(4-Cl-C6H4)-1,2,4-oY~A~;A7Ql-5 742 3-(2-Br-C6H4)-1,2,4-oYA~iA7ol-5-yl 743 3-(3-~3r-C6H4)-1,2 ~ 4 - OyA~ i A 701-5-yl 744 3-(4-Br-C6H4)-1,2,4-oYA~;A7Ql-5 745 3-(2-F-C6~4)-1,2,4-oY~i A 7~1-5-yl 746 3-(3-F-C6~)-1,2,4-o-Y~;A7Ql-5-yl 747 3-(4-F-C6H4)-1,2,4-oYA~iA7ol-5-yl 748 3-(2,4-Cl2-C6H3)-1,2,4-oYAA;A7ol-5 ~~ 749 3-(2,5-Cl2-C6H3)-1,2,4-nY~ 7-ol-5-y 750 3-(2,6-Cl2-C6H3)-1,2,4-nX~iA7Ql-5-yl 751 3-(3,4-Cl2-C6H3)-1,2,4-oYA~i~.7ol-5-yl 752 3-(2,4-F2-C6H3)-1,2,4-oY~;A-7ol-5-yl 20 753 3-(2,5-F2-C6H3)-1,2,4-oYA~;A7ol-5-yl 754 3-~2,6-F2-C6H3)-1,2,4-oYA~;A7-ol-5-yl 755 3 (3,4 F2-C6H3) 1,2,4-oYA~;A7ol 5 yl 756 3-(2-Cl, 5-OCH3-C6H3)-1,2,4-oYA~;A701-5-yl 757 3-(2-Cl, 5-CH3-C6R3)-1,2,4-nYA~A; A 701 - 5-yl 758 3-(5-Cl, 2-OCH3-C6H3)-1,2,4-oY~ 701-5-yl 759 3-(5-Cl, 2-CH3-C6H3)-1,2,4-nY~iA701-5-yl 760 3-t2~5-(CH3)2-C6~3]-1,2 ~ 4 - OYA~ i A 701-5-yl 761 5-CH3-1,2,4- th; A~;A701-3-yl 30 762 5-CH(CH3)2-1,2,4-~h;~i~A~ol-3-yl 763 5-C(CH3)3-1,2,4-~h;~ 701-3-yl 764 5-cyclopropyl-1,2,4-th;~;A7ol-3-yl 765 5-C6Hs-l~2~4-~h i A~;~ 701 - 3-yl 766 5-(2-CH3-C6H~)-1,2,4-th;~;A701-3-yl 767 5-(3-CH3-C6H4)-1,2,4-thiA~;A7ol-3-yl 768 5-(4-CH3-4H~)-1, 2, 4 - ~h ~ 701-3-yl 777 5-(3-OCH3-C6H~)-1, 2, 4-~h; A~i A 701-3-yl 770 5-(4-OCH3-C6H~)-1,2,4-~h;A~iA7~l-3 40 771 5-(4-N02-C6H4)-1,2,4-~h;~;~701-3-yl 772 5-(3-N02-C6H~)-1,2,4-~h~ 701-3-yl 773 5-(4-CN-C6H~)-1,2,4-~h i ~ ol-3-yl 774 5-(3-CN-C6H~)-1,2,4-th;~;A701-3-yl 775 5-(3-CF3-C6H4)-1,2,4-th;A~;~701-3-yl 776 5-(4-CF3-C6H~)-1,2,4-~h; ~A,~; A70l - 3 - yl 777 5-(4-C(CR3)3-C6H4)-1,2,4-~h~A~;A701-3-yl .
0050/45Z04 ' ~.',~v 225 2 1 9 9 ~ 2 2 No. Het 778 5-(4-C6Hs-C6B4)-1,2,4-~h;A~;A7Ol-3-yl 779 5-(2-Cl-C6H4)-1,2,4-thiAAiA7Ol-3-y 780 5-(3-Cl-C6H4)-1,2,4-th;~A7Ol-3-yl 781 5-(4-Cl-C6B4)-1~2~4-th; ~A~i A701-3-yl 782 5-(2-Br-C6H4)-1,2,4-~h;~;A7Ol-3 783 5-(3-Br-c6H4)-lr2~4-thi~;A7ol-3-yl 784 5-(4-~3r-C6H4)-1,2,4-th;A~;A~ol-3-yl 10 785 5-(2-F-C6H4)-1,2,4-~h.~A~;~7cl-3-yl 786 5-(3-F-C6H~)-1,2,4-~h;~;~701-3-yl 787 5-~4-F-C6H~)-1,2,4-th;A~;~7Ol-3 788 5-(2~4-clz-c6H3)-l~2,4-th~A~;~7Ql-3 15 789 5-(2,5-C12-C6H3)-1,2,4-th~;AZol-3-yl 790 5-(2,6-Cl2-C6H3)-1,2,4-~h;~;~7Ol-3-yl 791 5-(3,4-Cl2-C6H3)-1,2,4-~h;A~;~7Ol-3 792 5-(2,4-F2-C6H3)-1,2,4-th;~; A 701-3-yl 793 5-(2,5-FZ-C6H3)-1,2,4-th;A~iA7ol-3 20 794 5-(2,6-F2-C6H3)-1,2,4-th;A~;A7Ol-3 795 5-(3,4-F2-C6R3)-1~2,4-~h; A~; A ~701 - 3-yl 796 5-(2-C1~ 5-OCH3-C6H3)-1~2~4-th; A~; A 7~1- 3 - yl 797 5-(2-C1~ 5-CH3-C6H3)-1~2~4-~h; A~; A P01 - 3 - yl 798 5-(5-Cl~ 2-OCH3-C6H3)-1,2,4-th;A~;~701-3-yl 799 5-(5-C1~ 2-CH3-C6H3)-1~2~4-~h; A~; A70l - 3 - yl 800 5-~2,5-(CH3)2-C6H3]-1,2,4-th;A~;A7Ol-3 801 5-CH3-1,3,4-~hi A~; A7Ql - 2 - yl 802 5-CH(CH3)2-1,3,4-th;A~;A7Ol-2 30 803 5-C(CH3)3-1,3,4-~h;A~;A~1-2-yl 804 5-cyclG~ v~yl~l~3~4~thiA~;A7-Ol-2 805 5-C6Hs-1,3,4-thiadiazol-2-yl 806 5-(2-CH3-C6H4)-1,3,4-~h~A~;A7Ol-2-yl 807 5-(3-CH3-C6H4)-1,3~4-~h; A~ ~ A 701 - 2-yl 808 5-(4-CH3-C6H4)-1~3~4-~h;~ z701 - 2-yl 809 5-(3-OCH3-C6H4)-1,3,4-th;~;~7ol-2-yl 810 5-(4-OCH3-C6H4)-1,3~4-th;A~ 701 - 2-yl 811 5-(4-NO2-C6H4)-1,3,4-~h;A~;A7Ol-2-yl 40 812 5-(3-NO2-C6H4)-1~3~4-~h; A~; AZQl - 2 - yl 813 5-(4-CN-C6H~)-1,3,4-th;A~;R7Ol-2 814 5-(3-CN-C6H~)-1,3,4-thi~;A7ol-2 815 5-(3-CF3-C6H4)-1,3,4-thi~;A~cl-2-yl 816 5-(4-CF3-C6H4)-l~ 3~ 4-th~ A~; A70l - 2 - yl 817 5-(4-C(CH3)3-C6H4)-1,3,4-~h~;AZol-2 818 5~(4~C6Hs~C6H4)-1,3,4-th;a~zol-2-yl UU~ 3~U~
~ 226 ~99122 No. Het 819 5-(2 Cl-C6H4)-1,3,4-~h; A~i A701 2 yl 820 5-(3-Cl-C6~4)-1,3, 4 - th i ~ i A 701-2-yl 5 821 5-(4-Cl-C6H4)-1,3,4-thi A~i A 701-2-yl 822 5-(2-Br-C6H4)-1,3,4-~hi~; A 701 - 2 - yL
823 5-(3-.8r-CcH4)-1,3,4-th;~; A zol-2-yl 824 5-(4-Br-C6H4)-1,3,4-thi~iA7ol-2 825 5-(2-F-C6H~)-1,3,4-th;A~;A7ol-2-yl 10 826 5-(3-F-C6H4)-1,3,4-th;A~iA701-2-yl 827 5-(4-F-C6H~)-1,3,4-th;~;~701-2-yl 828 5-(2~4-cl2-c6H3)-l~3~4-thi A~; A 701-2-yl 829 5-(2~5-cl2-c6H3)-l~3~4-~h~ A~ A7~1 - 2 -15 830 5-(2,6-C12-CCH3)-1~3~4-~h;A~Ql-2-yl f 831 5-(3,4-C12-C6H3)-1,3,4-th; A~ ol-2-yl 832 5-(2,4-F2-C6H3)-1,3,4-~h;A~;A7ol-2-yl 833 5-(2,5-F2-C6H3)-1,3,4-th;A~;A701-2-yl 834 5-(2,6-F2-C6H3)-1,3,4-~h;A~;AZol-2 20 835 5-(3,4-F2-C6H3)-1,3,4-th;A~;A701-2-yl 836 5-(2-Cl, 5-ocH3-ccH3)-l~3~4-th;A~;Azol-2 837 5-(2-Cl, 5-cH3-c6H3)-l~3~4-th;~;A7ol-2 838 5-(S-Cl, 2-OCH3-C6H3)-1,3,4-~h;A~iA7ol-2 839 5-(5-Cl, 2-CH3-C6H3)-1,3,4-~hi ~A; A701 - 2 - yl 840 5-t2~5-(cH3)2-c6H3]-l~3~4-~h;~ 7ol-2 841 1,3-(CH3)2-pyrazol-4-yl 842 3-CH3, 1-CH(CH3)2-pyrazol-4-yl 843 3-CH3, l-C(CH3)3-pyrazol-4-yl 30 844 3-CH3, l-cyclop o~yl-pyrazol-4 845 3-CH3, 1-C6H5-pyrazol-4-yl 846 3-CH3, 1-(2-CH3-C6H4)-pyrazol-4-yl 847 3-CH3, 1-(3-CH3-C6H~)-pyrazol-4-yl 848 3-CH3, 1-(4-CH3-C6H~)-pyrazol-4-yl 849 3-CH3, 1-(3-OCH3-C6H4)-pyrazol-4-yl 850 3-CH3, 1-(4-OCH3-C6H4)-pyrazol-4-yl 851 3-CR3, 1-(4-N02-C6H4)-pyrazol-4-yl 852 3-CH3, 1-(3-N02-C6H~)-pyrazol-4-yl 40 853 3-CH3, 1-(4-CN-C6H~)-pyrazol-4-yl 854 3-CH3, 1-(3-CN-C6H~)-pyrazol-4-yl 855 3-CH3, 1-(3-CF3-C6H~)-pyrazol-4-yl 856 3-CH3, l-(4-CF3-C6H~)-pyrazol-4-yl 857 3-CH3, 1-(4-C(CH3)3-C6H4)-pyrazol-4-yl 858 3-CH3, 1-(4-C6H5-C6H4)-pyrazol-4-yl 859 3-CH3, l-(2-Cl-C6H~)-pyrazol-4-yL
0050/452~4 -227 2199~22 No. Het 860 3-CH3, 1-(3-Cl-CcH4)-pyrazol-4-yl 861 3-CR3, 1-(4-Cl-C6H4)-pyrazol-4-yl 862 3-CH3, 1-(2-~r-C6H4)-pyrazol-4-yl 863 3-CH3, 1-(3-}3r-C6H~)-pyrazol-4-yl 864 3-CH3, 1-(4-Br-C6H4)-pyrazol-4-yl 865 3-CH3, 1-(2-F-C6H~)-pyrazol-4-yl 866 3-CH3, 1-(3-F-C6H~)-pyrazol-4-yl 867 3-CH3, 1-(4-F-C6H4)-pyrazol-4-yl 868 3-CH3, 1-(2,4-C12-C6H3)-pyrazol-4-yl 869 3-CH3, 1-(2,5-C12-C6H3)-pyrazol-4-yl 870 3-CH3, 1-(2,6-C12-C6H3)-pyrazol-4-yl 871 3-CH3, 1-(3,4-C12-C6H3)-pyrazol-4-yl f 872 3-CH3, 1-(2,4-F2-C6H3)-pyrazol-4-yl 873 3-CH3, 1-(2,5-F2-C6H3)-pyrazol-4-yl 874 3-CH3, l-(2,6-F2-C6H3)-pyrazol-4-yl 815 3-CH3, 1-(3~4-F2-c6H3)-pyrazol-4-yl 876 3-CH3, 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 877 3-CH3, 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 878 3-CH3, 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 879 3-CH3, 1-(5-Cl, 2-CH3-C6H3)-pyrazol-4-yl 880 3-CH3, 1-[2,5-(CH3)2-C6H3]-pyrazol-4-yl 881 3,5-(CH3)2, 1-C6Hs-pyrazol-4-yl 882 3,5-(CH3)2, 1-(2-CH3-C6H4)-pyrazol-4-yl 883 3~5-(C~3) 2 ~ 1 - (3-cH3-c6H4)-pyrazol-4 884 3,5-(CH3)2, 1-(4-CH3-C6H4)-pyrazol-4-yl 885 3~5-(CH3) 2 ~ 1 - ( 3-ocH3-c6H4)-pyrazol-4 886 3~5-(CH3) 2 ~ 1 - ( 4-ocH3-c6H~)-pyrazol-4 887 3,5-(CH3)2, 1-(4-NO2-C6H~)-pyrazol-4-yl 888 3,5-(CH3)2, 1-(3-No2-c6H~)-pyrazol-4 889 3,5-(CH3) 2 ~ 1 - ( 4-CN-C6H~)-pyrazol-4-yl 890 3,5-(CH3)2, 1-(3-CN-C6H~)-pyrazol-4-yl 891 3,5-(CH3)2, 1-(3-cF3-4H4)-pyrazol-4 892 3~5-(CH3) 2 ~ 1 - ( 4-cF3-c6H4)-pyrazol-4-yl 893 3,5-(CH3)2, 1-(4-C(CH3)3-C6H~)-pyrazol-4-yl 894 3,5-(CH3)2, 1-(4-C6H5-C6H~)-pyrazol-4-yl 895 3,5-(CH3)2, 1-(2-Cl-C6H~)-pyrazol-4-yl 896 3,5-(CH3)2, 1-(3-Cl-C6H~)-pyrazol-4-yl 897 3,5-(CH3)2, 1--(4--Cl--C6H4)--pyrazol--4--yl 898 3,5-(CH3) 2 ~ 1 - ( 2-Br-C6H~)-pyrazol-4-yl 899 3,5-(CH3) 2 ~ 1 - (3-Br-C6H~)-pyrazol-4-yl 900 3,5-(CH3)2, 1-(4-Br-C6H~)-pyrazol-4-yl uu~u ~ ~v~
2~99 122 No. Het 901 3,5-(CH3)2, 1-(2-F-C6H4)-pyrazol-4-yl 902 3,5-(CH3)2, 1-(3-F-C6H~)-pyrazol-4-yl 903 3,5-(CH3)2, 1-(4-F-C6H4)-pyrazol-4-yl 904 3,5-(CH3)2, 1-(2,4-C12-C6H3)-pyrazol-4-yl 905 3,5-(C~3)2, 1-(2~5-cl2-c6H3)-pyrazol-4-yl 906 3,5-(CH3)2, 1-~2,6-Cl2-C6H3)-pyrazol-4-yl 907 3,5-(C~3)2, 1-(3~4-Cl2-C6H3)-pyrazol-4-yl 10 908 3,5-(CH3)2, 1-(2,4-F2-C6H3)-pyrazol-4-yl 909 3,5-(CH3)2, 1-(2,5-F2-C6H3)-pyrazol-4-yl 910 3,5-(CH3)2, 1-(2~6-F2-C6H3)-pyrazol-4-yl 911 3~5--(CH3)2~ 1--(3~4--F2--C6H3)--pyrazol--4-yl 15 912 3,5-(CH3)2, 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 913 3,5-(CR3)2, 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 914 3,5-(C~3)2, 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 915 3,5-(CH3)2, 1-(5-Cl, 2-CH3-C683)-pyrazol-4-yl 916 3~5-(CH3)2~ 2~5-(c83)2-c6H3]-pyrazol-4 gO
-229 2~99-;122 Table 779 CG~ OU11dS of the general formula I.B (n = 0) in which UR' i8 5 methoxy, VR" is methoxy, yb is oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 780 10 Co...p~lds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is methoxy, yb iS oxygen and Ab for a ~oh.~oulld corresponds to one of the groups ~tated in Table E
Table 781 ( Co.. pounds of the general formula I.B ~n = 0) in which UR' i8 methoxy, VR" is ethoxy, yb is oxygen and Ab for a ~v~ ound corresponds to one of the ~LU~S stated in Table E
20 Table 782 Co...~oul,ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethoxy, yb i8 oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 783 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is methoxy, yb is oxygen and Ab for a co~ ound 30 corresponds to one of the groups stated in Table E
' Table 784 Compounds of the general formula I.B (n = 0) in which UR' i8 35 ethylamino, VR" is methoxy, yb is oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 785 40 C~,.pGunds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is ethoxy, yb is oxygen and Ab for a c~ ound corresponds to one of the groups stated in Table E
~u~U~4~v~
230 2199~22 Table 786 Co~ ds of the general formula I.B (n = ~) in which UR' is ethylamino, VR" is ethoxy, yb iS oxygen and Ab for a compound 5 corresponds to one of the groups stated in Table E
Table 787 Compounds of the general formula I.B ~n = 0) in which UR' i8 10 methoxy, VRn is methylamino, yb iS oxygen and Ab for a ~ompound corresponds to one of the groups stated in Table E
Table 788 15 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb i8 oxygen and Ab for a co~ ound corresponds to one of the y~Ou~S stated in Table E
Table 789 Co,..~ ds of the general formula I.B (n = 0) in which UR' is methoxy, VR" i8 ethylamino, yb iS oxygen and Ab for a ~ oulld corresponds to one of the groups stated in Table E
25 Table 790 Co~ oul,ds of the general formula I.B (n = 0) in which UR' iB
ethoxy, VRn i8 ethylamino, yb is oxygen and Ab for a c~...~ound corresponds to one of the gL O~S stated in Table E
Table 791 ~ . .
CG~ ndS of the general formula I.B (n 5 O) in which UR' is methoxy, VR" is methoxy, yb is sulfur and Ab for a c~.,.pound 35 corresponds to one of the groups stated in Table E
Table 792 Co...~o~l-ds of the general formula I.B (n = 0) in which UR' is 40 ethoxy, VR" is methoxy, yb i8 sulfur and Ab for a c~...~ou~,d corresponds to one of the groups stated in Table E
.; . . .
Table 793 Cvlllpounds of the general formula I.B (n - 0) in which UR' is methoxy, VR" is ethoxy, yb iS sulfur and Ab for A c~...pound 5 corresponds to one of the groups stated in Table E
Table 794 Cor,.~o~nds of the general formula I.B (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yb is sulfur and Ab for a ~~v...~Gund corresponds to one of the yLUU~s stated in Table E
Table 795 15 CoLIl~oul-ds of the general formula I.B (n = 0) in which UR' is f methylamino, VR" i8 methoxy, yb is sulfur and Ab for a cv.. ,~oul.d corresponds to one of the groups stated in Table E
Table 796 Cu..lpounds of the general formula I.B (n 2 O) in which UR' is ethylamino, VR" is methoxy, yb is sulfur and Ab for a compound corresponds to one of the groups stated in Table E
25 Table 797 C~ unds of the general formula I.B (n = 0) in which UR' i methylamino, VR" is ethoxy, yb is sulfur and Ab for a cor..~our.d corresponds to one of the groups stated in Table E
Table 798 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is sulfur and Ab for a compound 35 corresponds to one of the groups stated in Table E
Table 799 .
Col..pounds of the general formula I.B (n - 0) in which UR' iQ
40 methoxy, VR" i8 methylamino, yb is sulfur and Ab for a co~ ~und corresponds to one of the groups stated in Table E
~050/4~204 ~~ 2I9gL¦~
Table 800 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yb iS sulfur and Ab for a cv,,.~ou,~d 5 corresponds to one of the groups stated in Table E
Table 801 CG..~o~lds of the general formula I.B (n = 0) in which UR' is 10 methoxy, VR" i8 ethylamino, yb is sulfur and Ab for a cv.,,~ound corresponds to one of the ylGU~S stated in Table E
Table 802 15 Compounds of the general formula I.B (n = 0) in which UR' is f ethoxy, VR" is ethylamino, yb iS sulfur and Ab for a compound corresponds to one of the groups stated in Table E
~ 219~f122 Table E
No. Ab 1 3-Fluoropyrid-2-yl 5 2 3-Chloropyrid-2-yl 3 3-Bromopyrid-2-yl 4 3-Methylpyrid-2-yl 3-Trifluoromethylpyrid-2-yl 10 6 3-Metho~y~Lid-2-yl 7 4-Fluo~ id-2-yl 8 4-Chloropyrid-2-yl 9 4-B.~ ~pyLid-2-yl 4-Methylpyrid-2-yl 15 11 4-Trifluoromethylpyrid-2-yl 12 4-Metho~y~yLid-2-yl 13 S-Fluo~pylid-2-yl 14 5-Chloropyrid-2-yl 20 15 5-Bl~ - p~L id-2-yl 16 5-Methylpyrid-2-yl 17 6-Trifluoromethylpyrid-2-yl 18 6-Methoxypyrid-2-yl 25 19 2-F1UOLV~Y L id-3-yl 2-Chlo~opy L id-3-yl 21 2-B,~ -~yrid-3-yl 22 2-Methylpyrid-3-yl 23 2-Trifluoromethylpyrid-3-yl 24 3-Metho~y~ylid-3 (-. 25 4-Fluoropyrid-3-yl 26 4-Chloropyrid-3-yl 27 4-Bromopyrid-3-yl 35 28 4-Methylpyrid-3-yl 29 4-Trifluoromethylpyrid-3-yl 4-Metho~y~yLid-3 31 5-Fluoropyrid-3-yl 40 32 5-Chloropyrid-3-yl 33 5-B.~- ~pyLid-3-yl 34 5-Methylpyrid-3-yl 5-Trifluoromethylpyrid-3-yl 45 36 5-Metho~y~yLid-3 37 6-Fluoropyrid-3-yl 38 Pyrid-2-yl No. Ab 39 Pyrid-3-yl Pyrid-4-yl 5 41 6-Chloropyrid-3-yl 42 6-BLu,.. o~y~id-3-yl 43 6-Methylpyrid-3-yl 44 6-Trifluoromethylpyrid-3-yl 6-Methoxypyrid-3-yl 46 2-Fluoropyrid-4-yl 47 2-ChloLop-yLid-4 48 2-Bromopyrid-4-yl 49 2-Methylpyrid-4-yl 15 50 2-Trifluoromethylpyrid-4-yl ( 51 2-Metho~y~yLid-4 52 3-Fluoropyrid-4-yl 53 3-Chloropyrid-4-yl 20 54 3-Bromopyrid-4-yl 3-Methylpyrid-4-yl 56 3-Trifluoromethylpyrid-4-yl 57 3-Metho~y~y,id-4-yl 4-Fluoropyrimidin-2-yl 59 4-Chloropyrimidin-2-yl 4-BL~ ~pyLimidin-2-yl 61 4-Methylpyrimidin-2-yl 62 4-Trifluoromethylpyrimidin-2-yl 30 63 4-Metho~y~yLimidin-2 64 5-Fluoropyrimidin-2-yl 5-Chloropyrimidin-2-yl 66 5-3romopyrimidin-2-yl 35 67 5-Methylpyrimidin-2-yl 68 5-Trifluoromethylpyrimidin-2-yl 69 5-Metho~y~yLimidin-2-yl 2-Fluoropyrimidin-4-yl 40 71 2-Chloropyrimidin-4-yl 72 2-BL~ ~pyLimidin-4-yl 73 2-Methylpyrimidin-4-yl 74 2-Trifluoromethylpyrimidin-4-yl 2-Trifluoromethylpyrimidin-4-yl 76 2-Metho~y~yLimidin-4 77 5-Fluoropyrimidin-4-yl U~U~4S~4 2199 ~22 No. Ab 78 5-Chloropyrimidin-4-yl 79 5-Bromopyrimidin-4-yl 5 80 5-Methoxypyrimidin-4-yl 81 5-Trifluoromethylpyrimidin-4-yl 82 5-Methoxy~yLimidin-4-yl 83 6-Fluoropyrimidin-4-yl 84 6-Chloropyrimidin-4-yl 6-Bromopyrimidin-4-yl 86 6-Methylpyrimidin-4-yl 87 6-Trifluoromethylpyrimidin-4-yl 88 6-Metho~y~yLimidin-4-yl 15 89 2-Fluoropyrimidin-5-yl ( 90 2-Chloropyrimidin-5-yl 91 2-~romopyrimidin-5-yl 92 2-Methylpyrimidin-5-yl 20 93 2-Trifluoromethylpyrimidin-5-yl 94 2-Methoxypyrimidin-5-yl 4-Fluoropyrimidin-5-yl 96 4-Chloropyrimidin-5-yl 97 4-Bromopyrimidin-5-yl 98 4-Methylpyrimidin-5-yl 99 4-Trifluoromethylpyrimidin-5-yl 100 3-Fluoro-5-trifluoromethylpyrid-2-yl 101 3,6-Dichloro-5-trifluoromethylpyrid-2-yl 30 102 5,6-Dichloro-3-trifluoromethylpyrid-2-yl 103 5-Chloro-3-trifluoromethylpyrid-2-yl 104 3-Chloro-5-trifluoromethylpyrid-2-yl 105 6-Chloro-4-cyanopyrid-2-yl 35 106 3-Cyano-5-nitropyrid-2-yl 107 2-Chloro-6-fluoropyrid-4-yl 108 6-Chloro-4-fluoropyrid-2-yl 109 4,6-Difluoropyrid-2-yl 40 110 3,5-Dichloro-6-fluoropyrid-2-yl 111 6-Methoxy-3-nitropyrid-2-yl 112 4-Cyano-6-fluoropyrid-2-yl 113 6-Chloro-5-cyanopyrid-2-yl 6-Chloro-3-cyanopyrid-2-yl 115 4-Cyano-3,5,6-trifluoropyrid-2-yl 116 6-Chloro-5-nitropyrid-2-yl 21g9~22 No. Ab 117 6-Chloro-3-nitropyrid-2-yl 118 5-Cyano-6-fluoLo~yrid-2 5 119 3-Cyano-6-fluoropyrid-2-yl 120 4,6-Dicyanopyrid-2-yl 121 5-Trichloromethylpyrid-2-yl 122 5-Cyanopyrid-2-yl 123 5-Bromo-4-trifluoromethylpyrid-2-yl 124 3-Nitro-5-trifluoromethylpyrid-2-yl 125 5-Formamidopyrid-2-yl 126 5-Aminopyrid-2-yl 127 2,3,5,6-Tetrafluoropyrid-4-yl 15 128 5-Nitropyrid-2-yl 129 4-methyl-5-nitropyrid-2-yl 130 5-Difluoromethylpyrid-2-yl 131 5-Fluoromethylpyrid-2-yl 20 132 4,6-Difluo~y~imidin-2-yl 133 2,6-Difluoropyrimidin-4-y}
134 2-Chloro-6-trichloromethylpyrimidin-4-yl 135 2,6-Dichloropyrimidin-4-yl 25 136 5-Methoxycarbonylpyrid-2-yl 137 5-Chloro-6-fluoropyrid-2-yl 138 5-Chloro-6-hydL O~y~yL id-2-yl 139 5-Chloro-6-methohy~ylid-2 140 5-Chloro-6-cyanopyrid-2-yl 30 141 5,6-Dichloropyrid-2-yl 142 6-Bromo-5-chloropyrid-2-yl 143 5-Chloro-6-aceto~y~yLid-2 144 S-Bromo-6-fluoropyrid-2-yl 35 145 5-Bromo-6-chloropyrid-2-yl 146 5-Bromo-6-cyanopyrid-2-yl 147 5-Bromo-6-hydro~y~ylid-2-yl 148 5-Bromo-6-metho~y~y~id-2-yl 40 149 5,6-DibL~ y id-2-yl 150 4-Cyanopyrid-2-yl 151 6-Cyanopyrid-2-yl 152 5-Chloropyrid-2-yl 153 4-Chloro-6-methylpyrimidin-2-yl 154 2-Choro-6-f 1UG~ ~~Y ~ id-4-yl 155 5-BL~ - ~ trifluoromethylpyrid-2-yl ~OS0~452U4 ~ 2199 i22 No. Ab 156 4,5-Dichloropyrid-2-yl 157 4,5-Dibromopyrid-2-yl 5 158 5,6-Dichlo~opy~id-2-yl 159 4,6-DichloL O~yL id-2-yl 160 4,6-Dibromopyrid-2-yl 161 5,6-Dibromopyrid-2-yl 162 4-~romo-5-chlolv~y.id-2-yl 163 6-Bromo-5-chloLo~y~id-2-yl 164 5-Bromo-4-chlo~ ~py r id-2-yl 165 5-Bromo-4-chlol ~pyL id-2-yl 166 6-3romo-4-chloropyrid-2-yl 15 167 4-Bromo-6-chloLo~Lid-2-yl r 168 6-Chloro-4-methoxypyrid-2-yl 169 6-~romo-4-metho~y~yLid-2-yl 170 6-Chloroquinazolin-2-yl 20 171 Quinazolin-2-yl 172 5-~enzyloxycarbonylpyridyl 173 4-Formylpyrid-2-yl 174 5-Formylpyrid-2-yl 25 175 6-Formylpyrid-2-yl 176 4-Cyanopyrid-2-yl 177 6-Cyanopyrid-2-yl 178 5-Hydroxymethylpyrid-2-yl 179 6-Chloro-4-trifluoromethylpyrid-2-yl 30 180 6-Chloro-4-trifluoromethylpyrid-2-yl 181 6-Chloro-4-methylpyrid-2-yl 182 2,5-Dichloro-6-cyanopyrid-2-yl 183 2,5-Dichloro-6-carboxypyrid-2-yl 35 184 2,5-Dichloro-6-methoxycarbonyl-pyrid-2-yl 185 4-Cyanopyrid-2-yl 186 6-Trifluoromethylpyrid-2-yl 187 6-Methoxycarbonylpyrid-2-yl 40 188 6-Ca~bo~y~yrid-2-yl 189 4-Pheno~y~yLid-2-yl 190 5-Phenoxy~Lid-2-yl 191 6-Phenoxy~-yrid-2 192 6-Chloropyrid-3-yl 193 4-Phenoxypyrimidin-4-yl 194 4-(4-Methylphenoxy)pyrimidin-4-yl ~0050/~5204 2 1 9 9 ~ 2 2 No. Ab 195 4-Phenoxypyrimidin-2-yl 196 4-(2-Fluorophenoxy)-pyrimidin-2-yl 5 197 4-Phenoxypyrimidin-6-yl 198 4-(4-Chlorophenoxy)pyrimidin-6-yl 199 4-(2-Pyridyloxy)pyrimidin-6-yl 200 4-(6-Chloro-2-pyridyloxy)pyrimidin-6-yl 201 4-(3-Pyridyloxy)pyrimidin-6-yl 202 4-(2-methyl-3-pyridyloxy)pyrimidin-6-yl 203 4-(4-Pyridyloxy)pyrimidin-6-yl 204 2-Furanyl 205 3-Furanyl 15 206 2-Thionyl 207 4-Chloro-2-thienyl 208 5-Chloro-2-thienyl 209 5-Bromo-2-thienyl 20 210 5-Nitro-2-thienyl 211 3-Thienyl 212 2-Chloro-3-thienyl 213 2-Bromo-3-thienyl 25 214 1-Methyl-3-pyrrolyl 215 1-Methyl-2-pyrrolyl 216 1-Benzofuran-2-yl 217 1-Benzofuran-3-yl 218 1-Benzothiophen-2-yl 30 219 1-Benzothiophen-3-yl 220 3-Pyrrolyl 221 2-Pyrrolyl 222 3-Indolyl 35 223 2-Indolyl 224 1-Methyl-3-indolyl 225 1-Methyl-2-indolyl 226 1-Methylpyrazol-4-yl 40 227 1-Methylpyrazol-3-yl 228 Isoxazol-3-yl 229 Isoxazol-4-yl 230 Isoxazol-5-yl 231 Isothiazol-3-yl 232 Isothiazol-4-yl 233 Isothiazol-5-yl ~ ~199~122 No. Ab 234 Oxazol-2-yl 235 Oxazol-5-yl 5 236 Oxazol-4-yl 237 Thiazol-4-yl 238 Thiazol-5-yl 239 Thiazol-2-yl 240 1-Methylimidazol-4-yl 241 1-Methylimidazol-5-yl 242 1-Methylimidazol-2-yl 243 1,2-Benzisoxazol-3-yl 244 1,2-Benzisothiazol-3-yl 15 24S l-Methylindazol-3-yl 246 Benzoxazol-2-yl 247 5-Chlorobenzoxazol-2-yl 248 6-Fluorobenzoxazol-2-yl 20 249 Benzothiazol-2-yl 250 5-Fluorobenzothiazol-2-yl 251 6-Fluorobenzothiazol-2-yl 252 Pyrido[3,2-d]thiazol-2-yl 25 253 (6-Chloro-pyrido)[3,2-d]thiazol-2-yl 254 1-Methyl-1,2,3-triazol-5-yl 255 1-Methyl-1,2,3-triazol-4-yl 256 1-Methyl-1,2,4-triazol-5-yl 257 1-Methyl-1,2,4-triazol-3-yl 30 258 1-Methyl-1,2,3,4-tetrazol-5-yl 259 2-Methyl-1,2,3,4-tetrazol-5-yl 260 5-Trifluoromethyl-1,3,4-thiadiazol-2-yl 261 6-Chlorobenzoxazol-2-yl 35 262 5-Fluorobenzoxazol-2-yl 263 5-Nitrothiazol-2-yl Table 803 40 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab i5 phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
~ 2199 122 Table 804 Cv~ uu~.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl 5 radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each c~,..pou~ld to a line of Table F
Table 805 Compounds of the general formula I.B (n = 0) in which UR' i8 methoxy, VR" is ethoxy, yb is oxygen and Ab i8 phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for 15 each compound to a line of Table F
Table 806 C~.l.pounds of the general formula I.~ (n = 0) in which UR' is 20 ethoxy, VR" is ethoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the comh;nation of the index o and of the R~ group corresponding for each compound to a line of Table F
25 Table 807 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the 30 combination of the index o and o~ the R~ group corresponding for each compound to a line of Table F
Table 808 35 CG~ ounds of the general formula I.B (n ~ 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each co.,.po~..d to a line of Table F
Table 809 Co~ ounds of the general formula I.B tn = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab i~ phenyl, this 45 phenyl radical carrying an -Oo~R~ group in the 3 position and the ~ 2199~22 combination of the index o and of the R~ group corresponding for each col"~o~nd to a line of Table F
Table 810 Compounds of the general formula I.3 (n = 0) in which UR' is ethylamino, VR~' is ethoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for 10 each com~urld to a line of Table F
Table 811 Compounds of the general formula I.B (n 3 O) in which UR' is 15 methoxy, VR" is methylamino, yb is oxygen and Ab i8 phenyl, this f phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table 812 C~...pounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the 25 comh;n~tion of the index o and of the R~ group corresponding for each co..~Gulld to a line of Table F
Table 813 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb is oxygen and Ab is phenyl, this ' phenyl radical carrying an -Oo~R~ gro~p in the 3 position and the comh; n~tion of the index o and of the R~ group corre~ponding for each compound to a line of Table F
Table ôl4 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb i8 oxygen and Ab is phenyl, this 40 phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
0050/452~4 2~9gl22 Table 815 CG~ ounds of the general formula I.B (n = 0) in which UR ' is methoxy, ~R" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 5 2-pyridyl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 816 C~l..p~unds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the co~hl n~tion of the index o and of the R~ group corresponding 15 for each cv...~u,,d to a line of Table F
( Table 817 Compounds of the general formula I.B ~n = 0) in which UR ' is 20 methoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each ~~vI..~ound to a line of Table F
25 Table 818 CG...~oullds of the general formula I.B (n = 0) in which UR ' is ethoxy, VR~' is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and 30 the combination of the index o and of the R~ group corresponding for each cv~ ound to a line of Table F
Table 819 35 CG.n~Gunds of the general formula I.B (n 8 O) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the co~h~n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 820 Compounds of the general formula I.3 (n = 0) in which UR' is ethylamino, VR is methoxy, yb is oxygen and Ab is 2-pyridyl, this 45 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and 2~994~2 the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 821 Co~..po~lds of the general formula I.~ (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding 10 for each compound to a line of Table F
Table ô22 Compounds of the general formula I.B (n = 0) in which UR ' is 15 ethylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this ( 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table ô23 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position 25 and the combination of the index o and of the R~ group corresponding for each cv,..~ou,ld to a line of Table F
Table 824 30 Compounds of the general formula I.B (n = 0) in which UR ' is ethoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 825 Compounds of the general formula I.B (n = 0) in which UR ' is methoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 40 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the comh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
~ 2199~22 Table 826 Co~ o~llds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 5 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 827 C~ oui~ds of the general formula I.B (n - 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 15 for each ~oh.pGund to a line of Table F
Table 828 Compounds of the general formula I.B (n = 0) in which UR' is 20 ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each cv~ o~nd to a line of Table F
25 Table 829 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an - Oo~R~ group in the 4 position and 30 the combination of the index o and of the R~ group corresponding - for each c. Eound to a line of Table F
. .
Table 830 35 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an - Oo~R~ group in the 4 position and the c~mh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 831 Compounds of the general formula I.B (n = o) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, 45 this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position ~ == = -.
and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 832 CG.,.~o~nds of the general formula I.B ~n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 10 for each ~ pound to a line of Table F
Table 833 Co,..pounds of the general formula I.B (n 3 O) in which UR' i~
15 methylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each ~v...~ur.d to a line of Table F
20 Table 834 Co,..~ounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and 25 the combination of the index o and of the R~ group corresponding for each c~ ~ulld to a line of Table F
Table ô35 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 836 Compounds of the general formula I.~ (n = 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 40 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each co...po~l-d to a line of Table F
.
0050/4~Z04 -246 2 1 9 g 4 2 2 Table 837 C~,~.~ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb i8 oxygen and Ab i8 2-pyridyl, this 5 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of ~able F
Table 838 C~..poul,ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 15 for each co.,.~o~,ld to a line of Table F
Table 839 Compounds of the general formula I.B (n - 0) in which UR' is 20 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each cv,~o~nd to a line of Table F
25 Table 840 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 30 position and the combination of the index o and of the R~ group - corresponding for each compound to a line of Table F
Table 841 35 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 842 Co.,.~Gu..ds of the general formula I.B (n s 0) in which UR ' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 45 pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 843 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of 10 the R~ group corresponding for each compound to a line of Table F
Table 844 Compounds of the general formula I.B (n = 0) in which UR' is 15 ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table 845 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR is ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 25 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 846 30 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, ' this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 847 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VRn is methylamino, yb is oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~ ulld to a line of Table F
248 2I99~22 Table 848 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb i5 oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 849 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group 15 corresponding for each compound to a line of Table F
Table 850 Compounds of the general formula I.B (n = 0) in which UR' is 20 ethoxy, VRn is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the comhinAtion of the index o and of the R~ group corresponding for each cv...~o~nd to a line of Table F
25 Table 851 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and 30 the combination of the index o and of the R~ group corresponding for each co,.,~ound to a line of Table F
Table 852 35 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in th~ 6 position and the combination of the index o and of the R~ group corresponding for each ov...~o~nd to a line of Table F
Table 853 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb iS oxygen and Ab is 2-pyrazinyl, this 45 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and .
~ 2I99ll22 the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 854 CG.,.~ounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i3 ethoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ ~roup corresponding lO for each ~vm~o~nd to a line of Table F
Table 855 Compounds of the general formula I.B ~n = 0) in which UR' is 15 methylamino, VR" is methoxy, yb is oxygen and Ab i8 2-pyrazinyl, f~ this 2-pyraz~nyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ~und to a line of Table F
20 Table 856 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb i8 oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 25 position and the combination of the index o and of the R~ group corresponding for ea~h cv.l.pound to a line of Table F
Table 857 30 Compounds of the general formula I.B (n = 0) in which UR' is ;- methylamino, VR i8 ethoxy, yb is oxygen and Ab i8 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 858 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR is ethoxy, yb is oxygen and Ab is 2-pyrazinyl, 40 this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the com~nation of the index o and of the R~ group corresponding for each compound to a line of Table F
-0050~45204 Table 859 Co~ unds of the general formula I.B (n = 0) in which UR' is methoxy, VR" i5 methylamino, yb is oxygen and Ab is 2-pyrazinyl, 5 this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 860 Co.~.~Gunds of the general formula I.B (n = 0) in which UR' i8 ethoxy, VRn is methylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group lS corresponding for each compound to a line of Table F
,f Table 861 C~ _u,lds of the general formula I.B (n - 0) in which UR' is 20 methoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination.of the index o and of the R~ group corresponding for each compound to a line of Table F
25 Table 862 Compounds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 30 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
2199~22 Table F
No. o R~
o COCH3 6 0 CH=NOCH3 7 0 C~CH3)-NOCH3 8 0. COOH
15 11 0 3-Cl-CcH~
12 0 3-CN-C6H~
20 lS 0 3-CH3O-C6H4 18 1 2-Cl-C6H4 25 19 1 2-Br-C6H~
1 2-CN-C6H~
21 1 2-NO2-C6H~
22 1 2-CF3-C6H~
23 1 2-CH3-C6H~
1 2-n-C3H7-C6H4 31 1 2-CH=NOCH3-C6H4 40 32 1 2-C(CH3)=NOCH3-C6H4 37 1 2-CONH2-C6H~
38 1 2-CSNH2-C6H~
2199~22 No. o R~
5 41 1 2-CH3C00-C6Hg 42 1 2-CH3C00-C6H~
51 1 2-CH3S02NH-C6H~
52 1 2-CH3S02NH-C6H~
53 1 2,6-Difluorophenyl 20 54 1 2,6-Difluorophenyl 1 2,6-Difluorophenyl 56 1 3,6-Difluorophenyl 57 1 3,6-Difluorophenyl 1 . 3,6-Difluorophenyl 59 1 3-Cl-pyrid-2-yl 1 3-Cl-pyrid-2-yl 61 1 3-Cl-pyrid-2-yl 62 1 3-CN-pyrid-2-yl 30 63 1 3-CN-pyrid-2-yl ( 64 1 3-CN-pyrid-2-yl 1 3-CH3-pyrid-2-yl 66 1 3-CH3-pyrid-2-yl 35 67 1 3-CH3-pyrid-2-yl 68 1 3-CH30-pyrid-2-yl 69 1 3-CH30-pyrid-2-yl 1 3-CH30-pyrid-2-yl 40 71 1 3-CSNH2-pyrid-2-yl 72 1 3-CSNH2-pyrid-2-yl 73 1 3-CSNH2-pyrid-2-yl 74 1 4-F-pyrid-3-yl 4 75 1 4-F-pyrid-3-yl 76 1 4-F-pyrid-3-yl 77 1 4-CN-pyrid-3-yl .
_ 2193~22 No. o R~
78 1 4-CN-pyrid-3-yl 79 1 4-CN-pyrid-3-yl 5 80 1 4-CH3-pyrid-3-yl 81 1 4-CH3-pyrid-3-yl 82 1 4-CH3-pyrid-3-yl 83 1 Pyrimidin-2-yl 84 1 Pyrimidin-2-yl 1 Pyrimidin-2-yl 86 1 2-CH3-pyrimidin-2-yl 87 1 2-CH3-pyrimidin-2-yl 88 1 2-CH3-pyrimidin-2-yl 92 0 Br 20 93 o CH3 gS 0 pyrid-2-yl 96 0 Pyrimidin-2-yl (CH3)3 100 1 n-C3H7 101 1 i-C3H7 30 102 1 pyrid-2-yl ( 103 1 1-pyrid-3-yl 104 1 2-F-pyrid-3-yl 105 1 2-Cl-pyrid-3-yl 35 106 1 2-CN-pyrid-3-yl 107 1 2-CH3-pyrid-3-yl 108 l 2-CH30-pyrid-3-yl 109 1 2-CSNH2-pyrid-3-yl 2199 1~2 Table 863 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each ~ ound to a line of Table G
Table 864 Cv..*vunds of the general formula I.B (n - 0) in which UR' i~
ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 15 corresponding for each cv...~ound to a line of Table G
Table 865 Co.~oullds of the general formula I.B (n = 0) in which UR ' is 20 methoxy, VR" i8 ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each co...~ou~d to a line of Table G
25 Table 866 Compounds of the general foL ~ I.B (n - 0) in which UR ' i8 ethoxy, VR" is ethoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position 30 and the combination of the index o and of the R~ group ( correspon~; ng for each col,.pou~.d to a line of Table G
Table 867 35 Compounds of the general formula I.B (n = o) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the combination of thè index o and of the R~ group corresponding for each compound to a line of Table G
Table 868 Compounds of the general formula I.B (n = o) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 45 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 869 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 10 corresponding for each c~ o~nd to a line of Table G
Table 870 Compounds of the general formula I.B (n = 0) in which UR' is 15 ethylamino, VR" is ethoxy, yb i5 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~",~o~nd to a line of Table G
20 Table 871 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR is methylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~
25 group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ou,.d to a line of ~able G
Table 872 30 Co.llpo~llds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is methylamino, yb i8 oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each cv...pound to a line of Table G
Table 873 C~ ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR is ethylamino, yb iS oxygen and Ab is pyrimidin-4-yl, 40 this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
OOSOt45204 2I9~'122 Table 874 Co..~oul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 875 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" .is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each compound to a line of Table G
f Table 876 Compounds of the general ~ormula I.B (n - 0) in which UR' is 20 ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
25 Table 877 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb i8 oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 30 position and the com~ination of the index o and of the R~ group - corresponding for each compound to a line of Table G
Table 878 35 C~ -ul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the co~bination of the index o and of the R~ group corresponding for each c~,llpG~nd to a line of Table G
Table ô79 CGll*o~nds of the general formula I.B (n - 0) in which UR' is methylamino, VR" i8 methoxy, yb is oxygen and Ab is 45 pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
~ 257 2199~22 group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 880 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 10 corresponding for each . 3und to a line of Table G
Table 881 Co,.,~ounds of the general formula I.B (n = 0) in which UR ' is 15 methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, ( this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each ~v...~ound to a line of Table G
20 Table 882 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 25 position and the combinat~on of the index o and of the R~ group corresponding for each ~ ~u,.d to a line of Table G
Table 883 30 Co...~ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
group in the 4 position and the combination of the index o and of the R~ group corresponding for each col..yG~nd to a line of Table G
Table 884 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn is methylamino, yb i5 oxygen and Ab is pyrimidin-2-yl, 40 this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
~9!3422 Table 885 Compounds of the general formula I.B (n = 0) in which UR ' is methoxy, VR" i5 ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, 5 this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 886 Compounds of the general formula I.B (n G o) in which UR ' is ethoxy, VR" i9 ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each ~-vl~.~ound to a line of Table G
( Table ô87 Compounds of the general formula I.B (n - 0) in which UR ' is 20 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each co~ Gund to a line of Table G
25 Table 888 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, thi~ pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 30 position and the combination of the index o and of the R~ group corresponding for each cv...~ound to a line of Table G
Table 889 3S Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~ ound to a line of Table G
Table 890 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR~' is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 45 pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position ~ 259 2199~22 and the combination of the index o and of the R~ group correspo~;ng for each co...po~lld to a line of Table G
Table 891 s Co...~ounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of 10 the R~ group corresponding for each c~ ou.ld to a line of Table G
Table 892 Compounds of the general formula I.B (n = 0) in which UR' i~
f 15 ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
20 Table 893 Cur..p~nds of the general formula I.B (n 5 O) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 25 position and the combination of the index o and of the R~ group corresponding for each cG..,~ound to a line of Table G
~able 894 30 Compounds of the general formula I.B (n = 0) in which UR' is ethylam. ino~ VR" is ethoxy, ~b is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 895 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the c~mh;n~tion of the index o and of the R~ group corresponding for each con.pou,ld to a line of Table G
0050/45~04 2199~22 Table 896 Co...~ ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and o~ the R~ group correspon~;ng for each compound to a line of Table G
Table 897 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VRn iS ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group 15 corresponding for each ~l"~ound to a line of Table G
Table 898 Compounds of the general formula I.B (n a O) in which UR' is 20 ethoxy, ~R" i8 ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each ~..,po~nd to a line of Table G
25 Table G
No. o R~
2 0 Cl 30 3 0 Br 9 0 CH=NOCH3 0 C(CH3)=NOCH3 13 0 C6Hs 0 3--Cl--C6H4 17 0 3-CH3-C6H~
, ~ 261 2199~22 No. o R~
Table 61 Cohl~ul~ds of the general formula I.A (n = 0), in which UR' i8 15 methoxy, VR" is methoxy, ya iS -CH2O-~ = bond to Aa) and Aa is f 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a ~or.,pound corresponding to one of the groups stated in Table C
20 Table 62 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VRn is methoxy, ya i5 -CH20-~ (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical CH~NORiii in the 4 25 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 63 30 Compounds of the general for~ula I.A (n = 0), in which UR' i8 l methoxy, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i9 2-methyl-5-chlorophenyl which carries a radical CH=NOR1ii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 64 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya is -cH2O-~ = bond to Aa) and A~ i8 40 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ =
72 2199~22 Table 65 Co~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to A~) and Aa is S 2-chloro-5-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 66 Compounds of the general formula ~.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~--*ound corresponding to one of the groups 15 stated in Table C
f Table 67 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and A~ is 2,5-dichlorophenyl which carries a radical CH=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 68 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CHsNORiii in the 4 ~0 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 69 35 Compounds of the general formula I~A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH-NORiii in the 3 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
Table 70 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 45 phenyl which carries a radical CH=NORiii in the 3 position, Riii 0050/4S204 f 73 219942~
for a co,.,~oulld corresponding to one of the g~oups stated in Table C
Table 71 Compounds of the general formula I.A (n ~ 0), in which UR' is methoxy, VR" is methoxy, ya is -CHzo-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a c~"~ound corresponding to one of the group~
10 stated in Table C
Table 72 Co.l*~unds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR" i8 methoxy, ya i~ -CH20-# ~-# = ~ond to Aa) and Aa is f 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a cv.,~ou,,d corresponding to one of the groups stated in Table C
~0 Table 73 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa is phenyl which carries a radical CtCH3)=NORiii in the 4 position, 25 Riii ~or a cv.ll~oul~d correspondi~g to one of the groups stated in Table C
Table 74 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# - bond to Aa) and Aa i8 phenyl which carries a radical C(CH3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the yLGU~S stated in Table C
Table 75 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 40 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y vU~S
stated in Table C
0050~4~204 219~22 Table 76 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i5 -CH2O-# (-~ = bond to Aa) and Aa i8 5 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 77 Compounds of the general form~ I.A (n - 0), in which UR' is methoxy, VR" ls methoxy, ya iS -CH20-# (~~ = bond to A~) and Aa is 2-fluorophenyl which carries a radical C(CH3)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f ~- Table 78 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C~CH3)=NORiii in the 4 position, Riii for a c~ pc-und corresponding to one of the groups stated in Table C
25 Table 79 Compounds of the general formula I.A (n = o)r in which UR' i methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 30 position, Riii for a ou.l.pound corresponding to one of the groups stated in Table C
Table 80 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-~ = bond to Aa) and A~ is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 81 Cor..~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 45 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 21~22 position, Rlii for a compound corresponding to one of the groups stated in Table C
Table 82 Compounds of the general formula I.A (n = 0), in which UR~ is ethoxy, VR~ i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, R~ii for a co~ v~lld corresponding to one of the yLVU~
10 stated in Table C
Table 83 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is f 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, R~ii for a compound corresponding to one of the groups stated in Table C
20 Table 84 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya i5 -CH20-# (-# o bond to Aa) and A~ is 2-methyl-5-chlorophenyl which carrieq a radical C(CH3)=NORiii in 25 the 4 position, Riii for a mpoulld corre~ponding to one of the groups stated in Table C
Table 85 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)zNORiii in the 4 position, Riii for a cv~,.pound corresponding to one of the groups stated in Table C
Table 86 CG...~v~llds of the general formula I.A (n = 0), in which UR~ is ethoxy, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 40 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co.,.~ound corre~ponding to one of the groups stated in Table C
~ 0050/i5204 2 199~2 Table 87 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 5 2,5-dichlorophenyl which carries a radical C(CH3)SNORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 88 Compounds of the general formula I.A (n 2 0 ) ~ in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C~CH3)=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
r Table 89 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# ~ bond to Aa) and Aa is phenyl which carriQs a radical C(CH3)sN0Riii in the 3 position, Riii for a compound COl L es~onding to one of the groups stated in Table C
25 Table 90 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ G bond to Aa) and Aa i8 phenyl which carries a radical C(CH3)=NORiii in the 3 position, 30 Riii for a compound corresponding to one of the groups stated in r Table C
Table 91 35 CG-.I~oullds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 92 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methoxy, Y~ i8 -CH20-# (-~ - bond to Aa) and A~ is 45 2-methylphenyl which carries a radical C(CH3)-NORiii in the 5 ~ 7 2199 122 position, Riii for a ~vrl~ound corresponding to one of the groups stated in Table C
Table 93 Co,l,~v~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methoxy, ya is -CH20-# (-~ 5 bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups stated in 10 Table C
Table 9~ .
C~ ounds of the general formula I.A (n - 0), in which UR' is 15 ethoxy, VRn is methoxy, ya i5 -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the yLvu~s stated in Table C
20 Table 95 Col..yo~llds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 25 position, Riii for a ~ y~nd corresponding to one of the groups stated in Table C
Table 96 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-* - bond to Aa) and A~ is f 2-methylphenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a c o~nd corresponding to one of the group~
stated in Table C
Table 97 Compounds of the general formula I.A (n = 0), in'which UR' i5 methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
78 2I994~2 Table 98 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 5 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 po~ition, Riii for a c~...pound corresponding to one of the groups stated in Table C
Table 99 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f"
Table 100 Cv.,,~ou.~ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 101 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 102 35 C~ _unds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to onè of the groups stated in Table C
Table 103 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 45 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii 219~ 122 in the 4 position, Riii ~or a cG~ ound corresponding to one of the groups stated in Table C
Table 104 CG.,*oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)zNORiii in the 4 position, Riii for a cG,..~ound corresponding to one of the 10 groups stated in Table C
Table lOS
Compounds of the general formula I.A (n 3 O) ~ in which UR' i8 15 methoxy, VR" is methoxy, ya is -CHzO-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a ~u~ o~.,d corresponding to one of the groups stated in Table C
20 Table 106 CG.II~UndS of the general formula I.A (n = 0), in which UR' is ethoxy, VR~' i8 methoxy, ya iS -CH2û-# (-~ m bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C~CH2CH3)=NORiii 25 in the 4 position, Riii for a c~ Eo~nd corresponding to one of the groups stated in Table C
Table 107 30 Co..,~uunds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i~ methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2,5-dichlorophenyl which carrie~ a radical C(CH2CH3)=NORiii in the 4 position, Rii$ for a compound corresponding to one of the groups stated in Table C
Table 108 Compounds of the general formula I.A (n = 0), in which UR' i5 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 40 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~.,~ou~ld corresponding to one of the groups stated in Table C
219~422 Table 109 CGIlpounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# ( - ~ 5 bond to Aa) and Aa is 5 phenyl which carries a radical C(CH2CH3)sNORiii in the 3 position, Riii for a ~r.,~ound corresponding to one of the groups stated in Table C
Table 110 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
Table 111 Co~ ounds of the general formula I.A (n s 0)~ in which UR' i8 20 methoxy, VR" is methoxy, ya is -CH20~ = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a cv~,.pGu~.d corresponding to one of the groups stated in Table C
25 Table 112 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 30 position, Riii for a cu,..~vul,d corresponding to one of the groups _~ stated in Table C
Table 113 35 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Rii1 for a compound corresponding to one of the groups stated in Table C
Table 114 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 2199~22 position, Riii for a-c~ oul.d corresponding to one of the groups stated in Table C
Table 115 Coh,~oullds of the general formula I.A (n s 0)~ in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~...pou"d corresponding to one of the groups 10 stated in Table C
Table 116 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya iS -CH20-# (-# ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cG~ ound corresponding to one of the groups stated in Table C
20 Table 117 Co...poullds of the general formula I.A (n = 0), in which UR' is methoxy, VR i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i9 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 25 position, Riii for a ~G..~ound corresponding to one of the groups stated in Table C
Table 118 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co~.l~ound corresponding to one of the groups stated in Table C
Table 119 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiLi in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 2~3~2~
Table 120 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is t 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 121 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" ~i8 methoxy, ya is -CH20-# (~~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
,,.
Table 122 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CHzCHzCH3)=NORiii in the 4 position, Riii for a ov,.,~ound corresponding to one of the groups stated in Table C
25 Table 123 Co,~.~vu.lds of the general formula I.A (n = 0), in which UR' is methoxy, VR~' is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii 30 in the 4 position, Riii for a compound corre~ponding to one o~ ~he groups stated in Table C
Table 124 35 Compounds of the general formula I.A (n 5 O) r in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ ~-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ~.ou~s stated in Table C
Table 125 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa i5 45 2-chloro-5-methylphenyl which carrie~ a radical C~CH2CH2CH3)=NOR
2 1 9 9 4 h 2 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 126 Co~ ullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NOR
in the 4 position, Riii for a compound corresponding to one of the 0 yL~S stated in Table C
Table 127 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methoxy, Y~ is -CH20-~ (-# ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 128 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiil in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in ~able C
Table 129 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the yLou~s stated in Table C
Table 130 Cor.l~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 40 phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a cG."pound corresponding to one of the groups stated in Table C
-~ ~ 2199~22 Table 131 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O~ s bond to Aa) and Aa is 5 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 132 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya iY -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a cG...~und corresponding to one of the groups 15 stated in Table C
f Table 133 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3) 2 ]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 134 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to AA) and Aa is phenyl which carries a radical C[CH(CH3) 2 ~=N0Riii in the 4 30 position, Riii for a co~ ound corresponding to one of the groups "....... stated in Table C
Table 135 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-~ - bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2~=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 136 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya iS -CH2O-# (-~ - bond to Aa) and Aa is 45 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a-compound corresponding to one of the groups stated in Table C
Table 137 Co...~o~,.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C~cH(CH3)2]sNORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in ~able C
Table 13 C~ ouLlds of the general formula I.A (n = 0), in which UR' i~
15 ethoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is ( 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a c~..,po~lld corresponding to one of the y~OU~S
stated in Table C
ao Table 139 Co~ oul~ds of the general formula I.A (n - 0), in which UR' is methoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CtCH(CH3)2~2NORiii in the 4 25 position, Riii for a cvr,~o~nd corresponding to one of the groups stated in Table C
Table 140 30 Compoundg of the general formula I.A (n = 0), in which UR' is .. ethoxy, VR" is methoxy, ya iS -CH20~ ~ bond to Aa) and AA i5 2-chlorophenyl which carries a radical C[CH(CH3)2]-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 141 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa i8 40 2,5-dimethylphenyl which carrie~ a radical ClCH(CH3) 2 ]=N0R~ii in the 4 position, Riii for a c~ Gund corresponding to one of the groups stated in Table C
0050~45204 219g~22 Table 142 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5 2,5-dimethylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 143 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C[CH(CH3) 2 ] =NORiii in the 4 position, Riii for a ~ ound corresponding to one of the 15 yLOU~ stated in Table C
( Table 144 Co...~ou,~ds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" is methoxy, yn is -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C[ CH ( CH3 ) 2 ] =NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 145 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, vR" i8 methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C[ CH ( CH3 ) 2 ] =NOR~ ii 30 in the 4 position, Riii for a co~pGulld corresponding to one of the -~ groups stated in Table c Table 146 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C[ CH ( CH3 ) 2 ~ =NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 147 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 45 2,5-dichlorophenyl which carries a radical C[CH(CH3)2]=NORiii in ~ 0050/45204 2 1 9 ~ 1 22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 148 Compounds of the general formula I.A (n 2 o)~ in which UR' is ethoxy, VR" is methoxy, ~a iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which ~arries a radical CtCH(CH3)2]~NORiii in the 4 position, Riii for a compound corresponding to one of the 10 groups stated in Table C
Table 149 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa i5 phenyl which carries a radical C[CH(CH3)2]=NORi~i in the 3 position, Riii for a cu~ nd corresponding to one of the groups stated in Table C
20 Table 150 compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical CtCH(CH3)2]=NORiil in the 3 25 position, Riii for a cv".~oulld corresponding to one of the y~o~g stated in Table C
Table 151 -30 C ~o~nds-of the qeneral for~ula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical ClCH(CH3) 2 ]=N0Riii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 152 Compounds of the general formula I.A (n 5 O) ~ in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa i8 40 2-methylphenyl which carries a radical CtCH(CH3) 2 ]-NORili in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
88 2 1 9 9 ~ ~ 2 Table 153 Co~ u~,ds of the general for~ula I.A (n s 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 5 phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a ~~o...~Gund corresponding to one of the groups stated in Table C
Table 154 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i.s methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
Table 155 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a co...poul,d corresponding to one of the groups stated in Table C
25 Table 156 C~ oullds of the general formula I.A ~n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 30 position, Riii for a co~pound corresponding to one of the groups stated in Table C
Table 157 35 Co...~ullds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i~
2-fluorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 158 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 45 2-fluorophenyl which carries a radical C(C6Hs)=NORiii in the 4 ~19~2 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 159 Co~ ul~ds of the general form~ I.A (n 5 O) ~ in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 - position, Riii for a co,.. ~o~lld corresponding to one of the groups 10 stated in Table C
Table 160 Co~ oullds of the general formula I.A (n = 0), in which UR' i5 15 ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to Aa) and Aa is ( 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a c~.l.pour.d corresponding to one of the groups stated in Table C
20 Table 161 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya iS -CH2O-# (-# = bond to Aa) and A~ is 2,5-dimethylphenyl which carries a radical C(C6H5)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 162 30 CG...~ounds of the general formula I.A (n - 0), in which UR' i8 - ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(C6Hg)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 163 Co..,pounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20~ # = bond to Aa) and Aa is gO 2-methyl-5-chlorophenyl which carries a radical C(C6H5)zNORiii in the 4 position, Ri~i for a compound corresponding to one of the groups stated in Table C
2I9~ i~2 Table 164 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5 2-methyl-~-chlorophenyl which carries a radical C(C6H5)eNORiii in the 4 position, Riii for a compound corresponding to one of the ~oup~ stated in Table C
Table 165 C~.,-~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
~. .
Tab~e 166 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-# ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Rili for a c~ ulld corresponding to one o~ the groups stated in Table C
25 Table 167 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya is -CH20-# ~~# 5 bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORii~ in the 4 30 position, Riii for a c~ ~ul~d corresponding to one of the groups - stated in Table C
Table 168 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 169 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 45 phenyl which carries a radical C(C6H5)=NORiii in the 3 position, 0050~45204 91 2I99~22 Riii for a compound corresponding to one of the groups stated in Table C
Table 170 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 10 Table C
Table 171 CG.I.~ounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methoxy, yA is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the S
position, Riii for a cv...~ound corresponding to one of the groups stated in Table c 20 Table 172 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VR" i8 methoxy, ya i8 -CH20-~ (-# = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 5 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 173 30 Compounds of the general formula I.A (n = 0), in which UR' i9 methoxy, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a ~o~ ound corresponding to one of the groups stated in Table C
Table 174 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methoxy, ya is -CH20-~ ~-# 2 bond to Aa) and Aa is 40 phenyl which carries a radical C(Cl)=NORili in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/45204 2 1 ~ ~ ~ 2 2 Table 175 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 5 2-methylphenyl which carries a radical C(Cl)=NOR111 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 176 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NOR11i in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
.
Table 177 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NOR1l1 in the 4 position, Ri11 for a compound corresponding to one of the groups stated in Table C
25 Table 178 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NORii1 in the 4 30 position, Rii1 for a compound corresponding to one of the groups stated in Table C
Table 179 35 Compounds ol the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NOR1i1 in the 4 position, R1ii for a compound corresponding to one of the groups stated in Table C
Table 180 Compounds of the general formula I.A (n = 0), in which UR' iS
ethoxy, VR" is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 45 2-chlorophenyl which carries a radical C(Cl)=NOR'i' in the 4 position, Riii for a cG..~Gu-ld corresponding to one of the groups stated in Table C
Table 181 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cc...~und corresponding to one of the groups 10 stated in Table C
Table 182 Compounds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR" is methoxy, ya iS -CH20-~ (-# c bond to Aa) and Aa i8 f 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riil for a ~o...~oulld corresponding to one of the groups stated in Table C
20 Table 183 Cv~younds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 184 30 Co...~oullds of the general formula I.A ~n = 0), in which UR' is - ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 185 Compounds of the general formula I.A tn 5 O) ~ in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 40 2-chloro 5 -thylphenyl which carries a radical C(Cl)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/~5204 2 I 9 ~ 1 2 ~
Table 186 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 5 2-chlo~o 5 ~ hylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 187 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups lS stated in Table C
( Table 188 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 189 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya i8 -CH20-~ (-# - bond to Aa) and Aa is phenyl which carries a radical C(Cl)sNORiii in the 3 position, Riii 30 for a compound corresponding to one of the groups stated in Table C
Table 190 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a cv...~ound corresponding to one of the groups stated in Table C
Table 191 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 45 2-methylphenyl which carries a radical C(Cl)=NORiii in the S
.
~ 219~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 192 C~ pu~llds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 5 position, Riii for a cG.I.~u~nd corresponding to one of the groups 10 stated in Table C
Table 193 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methoxy, ya i8 -CH20-# ( -# 2 bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~ oul~d corresponding to one of the groups stated in Table C
20 Table 194 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-* = bond to Aa) and A~ is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 195 30 Compounds of the general formula I.A (n = 0), in which UR' is .. methoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the group~
stated in Table C
Table 196 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (~~ ~ bond to Aa) and Aa is 40 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~ pound corresponding to one of the groups stated in Table C
21 9~'~2~
Table 197 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 5 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a oo,.,~vund corresponding to one of the ~.o~s stated in Table C
Table 198 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" i-s methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 199 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y~ S
stated in Table C
25 Table 200 Compounds of the general formula I.A (n 2 O) ~ in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-~ = bond to A~) and A~ is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 30 position, Riii for a cor..~ound corresponding to one of the groups -~ stated in Table C
Table 201 35 Compounds of the general formula I.A (n 3 O) ~ in which UR' is methoxy, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, RLii for a compound corresponding to one of the groups stated in Table C
Table 202 Compound~ of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i5 45 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 0050/45204 2 ~ g 9 1 2 2 position, Riii for a-cv~ ound corresponding to one of the groups stated in Table C
Table 203 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methoxy, ya is -CH2O~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a ~ ound corresponding to one of the 10 groups stated in Table C
Table 204 C~llpo~nds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is f 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a col"~o~lld corresponding to one of the groups stated in Table C
20 Table 205 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in 25 the 4 position, Riii for a coh.~oul,d corresponding to one of the groups stated in Table C
Table 206 30 Compounds of the general formula I.A (n - 0), in which UR' i8 ,- ethoxy, VR" is methoxy, ya iS -CH2O-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 207 Co..~ounds of the general formula I.A (n 2 O) ~ in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 40 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 21994~
Table 208 .
Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya iS -CHzO-# (-# c bond to Aa) and Aa is 5 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cvl,~ound corresponding to one of the groups stated in Table C
Table 209 C~l..pounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and An i5 phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a c~..,pou.ld corresponding to one of the groups stated in 15 Table C
,. .
Table 210 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a c~ o~--d corresponding to one of the groups stated in Table C
25 Table 211 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)2NORiii in the 5 30 position, Riii for a c~ pound corresponding to one of the groups - stated in Table C
Table 212 35 Co.-.~ounds of the general formula I.A (n 5 O) ~ in which UR' i5 ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 213 Compounds of the general formula I.A (n e O) ~ in which UR' is methoxy, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa is 45 phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 OOg~4$~ 4 2199~22 position, Riii for a c~ ou~.d corresponding to one of the groups stated in Table C
Table 214 Co,~.~ou~-ds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 215 . ~~ -Compounds of the general formula I.A (n = O), in which UR' is 15 methoxy, VR is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is ~ 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 216 Compounds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in 25 the 4 position, Riii for a cor..pould corresponding to one of the groups stated in Table C
_ Table 217 30 Compounds of the general formula I.A (n = O), in which UR' is _ methoxy, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 218 Compounds of the general formula I.A (n = O), in which UR' i9 ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 40 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, R~ or a ~o...~ou,~d corresponding to one of the groups stated in Table C
0050~45204 2 1 9 9 ~ 2 2 Table 219 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (~~ = bond to Aa) and Aa is 5 2-chlorophenyl which carries a radical C~cyclopropyl)=NORiii in the 4 position, RiLi for a compound corresponding to one of the groups stated in Table C
Table 220 Co,.,~nds of the general formula I.A (n ~ O), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii ~or a compound corresponding to one of the 15 groups stated in Table C
(r Table 221 Co.~ u.,ds of the general formula I.A (n = 0), in which UR' i8 20 methoxy, VR" is methoxy, Y~ is -CH20-# (-# - bond to A~) and A~ i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NOR~ii in the 4 position, Riii for a co~..po~nd corresponding to one of the groups stated in Table C
25 Table 222 C~.~o~,~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# 5 bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(cyclopropyl)sNORiii 30 in the 4 position, Riii for a ~ o~nd corresponding to one of the f- groups stated in Table C
Table 223 35 Co,.,~ound~ of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, Y~ is -CH2O-# (-~ 8 bond to Aa) and Aa i5 2-methyl-5-chlorophenyl which carries a radical ~
C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 224 Co...pounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i~ -CH20-~ 5 bond to Aa) and Aa is 45 2-methyl-5-chlorophenyl which carries a radical U05U/ 4~
C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 225 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# ( -~ 5 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv...~ound 10 corresponding to one of the groups stated in Table C
Table 226 C~..po~lds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is f~ 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cG.,.pound corresponding to one of the groups stated in Table C
20 Table 227 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii 25 in the 4 position, Riii for a c--~,ound corresponding to one of the groups stated in Table C
Table 228 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH2O-~ (-# = bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 229 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 40 phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a cvr,lpo~nd corresponding to one of the y~U~S
stated in Table C
0050,45204 219~22 Table 230 Compounds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methoxy, ya iS -CH2O-# ~-~ = bond to Aa) and Aa is 5 phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a co...~vulld corresponding to one of the groups stated in Table C
Table 231 Co...~o~lds o~ the general formula I.A (n = 0), in which UR' is methoxy, VR".is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
f Table 232 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound c~ ~esponding to one of the groups stated in Table C
25 Table 233 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is phenyl which carries a radical C(CF3)3NORiii in the 4 position, 30 Riii for a Ct, GUnd corresponding to one of the groups stated in !~- Table C
Table 234 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and A~ is phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
gO
Table 235 Compounds of the general formula I.A (n e o), in which UR~ is methoxy, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and A~ is 45 2-methylphenyl which carries a radical C(CF3)~NORiii in the 4 = = ~ ~
U~S~/4S~4 2 1 9 ~ 2 position, Riii for a compound corresponding to one of the y vu~g stated in Table C
Table 236 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methoxy, ya iS -CH20-# (-# s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii ~or a compound corresponding to one of the groups 10 stated in Table C
Table 237 Compounds of the general formula I.A (n - 0), in which UR' is 15 methoxy, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 238 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VRn i8 methoxy, ya i8 -CH20-# (-~ ~ bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)sNORiii in the 4 25 position, Riii for a coll.pv~nd corresponding to one of the groups stated in Table C
Table 239 30 Compounds of the general formula I.A (n = 0), in which UR' is ,~ methoxy, VR" i8 methoxy, ya is -CH20~ 5 bond to Aa) and Aa is ~ 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a c~.l.pound corresponding to one of the groups stated in Table C
Table 240 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya i8 -CH20-# (-# s bond to Aa) and Aa is 40 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv,,.~oulld corresponding to one of the groups stated in Table C
~ 4~U4 Table 241 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methoxy, ya is -CH2O-# (-~ = bond to Aa) and Aa is 5 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
Table 242 C~m~ounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups 15 stated in Table C
Table 243 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 244 Co~ ounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methoxy, ya is -CH2O-# (-~ - bond to Aa) and Aa i5 2-~ethyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in 30 the 4 position, Riii for a c. --ulLd corresponding to one of the ~- - yL ~3 stated in Table C
Table 245 ~5 Compounds of the general formula I.A (n 5 O) ~ in which UR' i8 methoxy, VR" is methoxy, ya iS -C~20-~ (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ~LoU~s stated in Table C
Table 246 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methoxy, ya iS -cH2o-# (-# = bond to Aa) and Aa is 45 2-chloro 5 ~-thylphenyl which carries a radical C(CF3)=NORiii in U~5~/45~U4 ~ 105 2199~22 the 4 position, R~ for a compound corresponding to one of the groups stated in Table C
Table 247 Compounds of the general formula I.A (n 2 O) t in which UR' is methoxy, VR" is methoxy, ya iS -CH2O-~ = bond to Aa) and Aa i8 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Rili for a ~v.,.~uLld corresponding to one of the groups 10 ~tated in Table C
Table 248 Compounds of the general formula I.A (n = 0), in which UR' is lS ethoxy, VR" is methoxy, ya i8 -CH20-# (~# 5 bond to Aa) and Aa is f 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 249 Compounds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, 25 Riii for a ~v..,pound corresponding to one of the y~OU~S stated in Table C
Table 250 30 Compounds of the general formula I.A (n = 0), in which UR' is -- ethoxy, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa ~s phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 251 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa i8 40 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a ~."~und corresponding to one of the groups stated in Table C
2199 1~2 Table 252 Compounds of the general formula I.A (n e O) ~ in which UR' is ethoxy, VR" is methoxy, ya is -CH20-~ (-# = bond to A~) and Aa is 5 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 253 Compounds of the general formula I.A (n - 0), in which UR' i8 methylamino,.VR" is methoxy, ya i8 -CH20-# (-# 5 bond to Aa) and Aa iB phenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in 15 Table C
( Table 254 Compounds of the general formula I.A ~n = 0), in which UR' i8 20 ethylamino, VR~ is methoxy, ya is -CH20-~ (-# = bond to Aa) and A~
is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the yLo~ stated in Table C
25 Table 255 Col..p~ullds of the general formula I.A (n = 0), in which UR' is methylamino, VR~ i8 methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 30 position, Riii for a co...pound corresponding to one of the groups ~- stated in Table C
Table 256 35 C~Lsunds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 257 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ 5 bond to Aa) and 45 Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 ~u:~u~ ~
~99~22 position, Ri~i for a coll.~ou.~d corresponding to one of the groups stated in Table C
Table 258 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 259 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, yA is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 260 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and A~
is 2-chlorophenyl which carries a radical CH=NORiii in the 4 25 position, Riii for a co.,.~ound corresponding to one of the groups 8 tated in Table C
Table 261 30 Co...po~nds of the general formula I.A (n = 0), in which UR' i8 . methylamino, VRn is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 262 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, YR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
OU50/45~4 108 219~ i22 Table 263 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and S Aa is 2-~ethyl-5-chlorophenyl which carries a radical CHeNORiii in the 4 position, Riii for a cu~ u,~d corresponding to one of the groups stated in Table C
Table 264 Compounds of the general formula I.A (n = 0), in which ~R' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~",~ound corresponding to one of the 15 groups stated in Table C
f, Table 265 Cum~ou-.ds of the general Cormula I.A (n = 0), in which UR' i5 20 methyla~ino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a co~ o~nd corresponding to one of th groups stated in Table C
25 Table 266 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carrie~ a radical CH=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
Table 267 35 Cv..,~o~nds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-# ~-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ~l~uyS
stated in ~able C
Table 268 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa 45 is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 ~U~U~45~u~
2 1g9~22 position, Riii for a ~o,lpound corresponding to one of the groups stated in Table C
Table 269 Co...po~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 3 position, Riii for a ~vr,.~ou..d corresponding to one of the groups stated in 10 Table C
Table 270 C~ _vul~ds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa i8 phenyl which carries a radical C~Z~oRiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 271 Compounds of the general formula I.A (n = 0), in which UR' iQ
~ethylamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa iB 2-methylphenyl which carries a radical CH=NORlii in the 25 position, Riii for a cv~ ound corresponding to one of the y ou~
stated in Table C
Table 272 30 Co...poullds of the general formula I.A (n = 0), in which UR' i5 ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 273 Compounds of the general formula I.A (n = 0), in'which UR' is methylamino, VR" i8 methoxy, ya is -CH20-# (-~ = bond to Aa) and 40 Aa i8 phenyl which carries a radical C(CH3)~NOR~i~ in the 4 position, Riii for a cv.,.~oul~d corresponding to one of the yLvU~s stated in Table C
2~99~22 Table 274 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and A~
5 is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 275 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, .VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' ' Table 276 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 277 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a co.,.pvul,d corresponding to one of the groups stated in Table C
. . .
Table 278 35 C pvul.ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -cH2o-# (-~ = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 279 Cv~ ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the ~u~u~ ~v~
~ 111 2199q~2 4 position, Riii for a c~l~.pound corresponding to one of the groups stated in Table C
Table 280 Co~pounds of the general formula I.A ( n ~ O ), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-* (~~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a cG~ und corresponding to one of the groups lO stated in Table C
Table 281 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VRn is methoxy, ya iS -CH2O-# (-# ~ bond to A~) and Aa is-2,5-dimethylphenyl which carries a radical C(CH3)=NORlii in the 4 position, Riii for a c~ v~lld corresponding to one of the groups stated in Table C
2Q Table 282 .
Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 25 4 position, Riii for a cG,..~oul,d correspon~ng to one of the groups stated in Table C
Table 283 30 Compounds of the general formula I.A (n = 0), in which UR' is -- methylamino, VR" is methoxy, ya i5 -CH20~ = bond to Aa) and - Aa i8 2-methyl-5-chlorophenyl which carries a radical C(CH3)~NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 284 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i5 -CH20-# (~~ = bond to Aa) and A~
40 is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=~ORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
., 112 219942~
Table 285 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co".~und correspondiny-to one of the groups stated in Table C
Table 286 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-* (-# = bond to Aa) and A~
is 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
- - .
Table 287 Compounds of the general formula I.A ~n = 0), in which UR' is 20 methylamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa i5 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 288 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a ~o~ ound corresponding to one of the y~OU~S
stated in Table C
Table 289 35 Co.l.pounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the yLOu~s stated in Table C
Table 290 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa 45 is phenyl which carries a radical C(CH3)-NORiii in the 3 position, .
113 2199~22 Ri~i for a compound corresponding to one of the groups stated in Table C
Table 291 s Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in ~he S position, Ri~i for a co...~und corresponding to one of the groups 10 stated in Table C
Table 292 Compounds of the general formula I.A (n - 0), in which UR' i9 15 ethylamino, VR" is methoxy, ya iS -CH20-~ z bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Rii1 for a co~ ound corresponding to one of the groups stated in Table C
20 Table 293 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa i9 phenyl which carries a radical C(CH2CH3)=NORiii in the 4 25 position, Riii for a cG...~oulld corresponding to one of the groups stated in Table C
Table 294 30 Co."p~u.lds of the general formula I.A (n = 0), in which UR' is ethylaminoj VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cG...~ound corresponding to one of the groups stated in Table C
Table 295 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya iS -CH2O-# (-~ = bond to A~) and 40 Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLOU~S stated in Table C
00~0/45204 Table 296 Cu.,.~o~.ds of the general formula I.A (n = 0), in which UR' is ethyl~ino, VR" is methoxy, ya is -CH20-# (-~ ~ bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~..,pou~-d corresponding to one of the groups stated in Table C
Table 297 Cu.l.~uu~lds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, R~ii for a c~..,pound corresponding to one of the 15 groups stated in Table C
( Table 298 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya i~ -CH20 - # (-# 2 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cG...~Gu~.d corresponding to one of the groups stated in Table C
25 Table 299 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CHzO-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
Table 300 35 Cv~ Gullds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CHzO-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table ~01 Cv...~ou..ds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)-NOR
~S~/4S~4 ~99I22 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 302 Cv.~l~o~.lds of the general formula I.A ~n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv,llp~ulld corresponding to one of the 10 groups stated in Table C
Table 303 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" i8 methoxy, ya i8 -CH20-# (~~ = bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv.ll~v~nd corresponding to one of the groups stated in Table C
~ 20 Table 304 Compounds of the general formula I.A (n s 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to A~) and A~
is 2-methyl-S-chlorophenyl which carries a radical 25 C(CH2CH3)=NORiii in the 4 position, Riii for a cv.,*ound corresponding to one of the yL ~9 stated in Table C
Table 305 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i5 methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa i8 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv.,,~ound corresponding to one of the groups stated in Table C
Table 306 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
40 is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv~ ound corresponding to one of the groups stated ~n Table C
~U5~J45~4 2lgg~22 Table 307 Compounds of the general formula I.A (n = 0), in which UR~ is methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and 5 Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups ~tated in Table C
Table 308 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, UR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
(' Table 309 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a cv,,.~ound corresponding to one of the y.~S
stated in Table C
25 Table 310 Compounds of the general formula I.A (n ~ 0), in which UR' i8 ethylamino, VRn is methoxy, ya iS -CH2O-~ (-# = bond to A~) and Aa is phenyl which carries a radical C(CH2CH3)-NORiii in the 3 30 position, Riii for a compound corresponding to one of the y-O~S
. stated in Table C
;...
Table 311 35 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-$ 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 312 Compounds of the general form~ I.A (n - 0), in which UR' is ethylamino, VR~' is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa 45 is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the ~iu:~ù~ ~u~
5 position, Riii for ~ compound corresponding to one of the groups stated in Table C
Table 313 Co"~unds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ e bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 314 Co~ oundq of the general formula I.A (n ~ 0), in which UR' is 15 ethylamino, VR" is methoxy, ya i8 -CH20-# ~-# = bond to Aa) and Aa . is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~ pound corresponding to one of the g- Gup~
stated in Table C
20 Table 315 CGl~o~nds of the general formula I.A (n - 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 25 the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 316 30 C~ ou..ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR'! i8 methoxy, ya is -CH2O~ = bond to A~) and Aa .~ is 2-methylphenyl which carries a radical C(CH2CH2CH3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 317 CG...pou~lds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co~ und corresponding to ~ne of the yL~ups stated in Table C
118 2199~2 Table 318 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa 5 is 2-fluorophenyl which carries a radical C(CB2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 319 Compounds of the general formula I.A (n = 0), in which UR' is methylamino,.VR" is methoxy, ya is -cH2o-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 320 C~.l,poul.ds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 321 Cu,..~ou,lds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ i5 -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical 30 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co...~oulld corresponding to one of the groups stated in Table C
Table 322 35 Compounds of the general formula I.A (n = 0)~ in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLOu~s stated in Table C
Table 323 Co."~unds of the general formula I.A (n = 0), in which UR' i~
methylamino, VR" is methoxy, ya is -CH20-# (-~ ~ bond to Aa) and 45 Aa is 2-methyl-5-chlorophenyl which carries a radical ~S~4~U~ ~ ' ll9 2199~22 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~.,.pG~nd corresponding to one of the groups stated in Table C
Table 324 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and A~
is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound 10 corresponding to one of the groups stated in Table C
Table 325 Co~.,p~unds of the general formula I.A (n = 0), in which UR' is 15 methyl~m; no, VR" is methoxy, ya iS -CH20-# (-~ = bond to AA) and ~~ Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a co.~.po~nd cor~esponding to one of the groups stated in Table C
20 Table 326 C~...pou~lds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya i8 -CH20-# (-# - bond to Aa) and A~
is 2-chlo-o 5 ~-thylphenyl which carries a radical 2S C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cvm~n corresponding to one of the yLvu~s stated in Table C
Table 327 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-~ = bond to Aa) and Aa i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 328 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR~ is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa 40 i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the ylOU~S stated in Table C
0050/45204 ~'~
120 2 1 9 g 4 2 2 Table 329 Compounds o~ the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 5 Aa is phenyl which carries a radical C(CH2CH2CH3)-NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 330 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ - bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 331 Cu,l.~ounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 332 Co~..pou.lds o~ the general formula I.~ (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-~ 2 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 30 the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 333 35 CGn.~oullds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i8 methoxy, ya i8 -CH20-# (-$ = bond to Aa) and Aa is phenyl which carries a radical CtCH~CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 334 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa 45 is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 ~ 219g~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 335 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C~CH(CH3) 2 ]~NORiii in the 4 position, Ri1i for a co".~ul,d corresponding to one of the 10 groups stated in Table C
Table 336 Co..,poullds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa ( is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 po~ition, Riii for a c~ ,d corresponding to one of the yLOu~S stated in Table C
20 Table 337 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical ClCH(CH3)2]=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 338 30 Co,.,pou~ds of the general formula I.A (n = 0), ln which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a co,~.~ound corresponding to one of the groups stated in Table C
Table 339 Cor..pounds of the general formula I.A (n - 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-~ (-# - bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical CtCH(CH3) 2 ]=N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
122 2 1 9 g 4 2 2 Table 340 C~ u.lds of the general formula I.A ~n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa S is 2-chlorophenyl which carries a radical C~CH(CH3) 2 ]=N0Riii in the 4 position, Ri~i for a cv,..~ound corresponding to one of the groups stated in Table C
Table 341 Cor..~ou~-ds of the general ~ormula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3)2]=NORii~
in the 4 position, Rii~ for a compound corresponding to one of the 15 groups stated in Table C
f Table 342 C~ ullds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VRn is methoxy, ya i5 -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C~CH~CH3) 2 ] =NoRiil in the 4 position, Rlii for a c~ u..d corresponding to one of the groups stated in Table C
25 Table 343 Com~u~l,ds of the general fo~ I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 ClCH(CH3)2]2NORiii in the 4 position, Riii for a co~ d corresponding to one of the group~ stated in Table C
. .
Table 344 ~5 Compounds of the general formula I.A (n - 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A' is 2-methyl-5-chlorophenyl which carries a radic~l C~CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 345 Compounds of the general formula I.A (n - 0), in which UR' is methylamino, VR" i5 methoxy, ya iS -CH20-# (-# z bond to Aa) and 45 Aa is 2-chloro-5-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a o~ Gulld corresponding to one o~ the groups stated in Table C
Table 346 Compounds of the general formula I.A (n ~ ~) r in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# ~ bond to Aa) and Aa is 2-chlo-o 5 methylphenyl which carries a radical C~CH(CH3)2]SNORiii in the 4 position, Riii for a cv,,l~ound 10 corresponding to one of the groups stated in Table C
Table 347 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CtCH(CH3)2]=NORiii in the 4 position, Riii for a c~ ou~,d corresponding to one of the groups stated in Table C
20 Table 348 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C[CH(CH3) 2]=NORiii 25 in the 4 position, Riii for a cG",~ound corresponding to one of the groups stated in Table C
Table 349 30 Compounds of the general formula I.A (n = 0), in which UR' is - methyl ~mi no, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is phenyl which carries a radical C~CH(CH3)2]=NORiii in the 3 position, Riii for a co"i~o~,d corresponding to one of the ~LoUps stated in Table C
Table 350 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 351 C~,.,po~llds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-methylphenyl which carries a radical C[CH(CH3)2~=NORi~i in the 5 position, Riii for a compound corresponding to one of the y~O~S stated in Table C
Table 352 Co,..~G~llds of the general formula I.A (n s 0), in which UR' i5 ethylamino, VRI' is methoxy, ya i8 -CH20-~ 3 bond to Aa) and A~
is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 5 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 353 Co".pou~ds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, Y~ is -CH2O-# (-# 5 bond to Aa) and Aa i8 phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a o~ ,u~ld corresponding to one of the yLo~
stated in Table C
25 Table 354 CGh.pG~.lds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6B5)~NORiii in the 4 30 position, Riii for a compound corresponding to one of the yl~U~3 stated in Table C
~.
Table 355 35 Cc ~.~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-# (-# ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 356 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# ~ bond to A~) and Aa 45 is 2-methylphenyl which carries a radical C(C6Hs)2NORill in the 4 219g~22 position, Riii for a-compound corresponding to one of the groups stated in Table C
Table 357 C~ o~l.ds of the general formula I.A (n 2 O) ~ in which UR' i8 methylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6~5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 358 Compounds of the general formula I.A (n = 0), in which UR' i8 15 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa f is 2-fluorophenyl which carries a radical C(C6H5)eNORiii in the 4 position, Riii for a co...~o~nd corresponding to one of the groups stated in Table C
20 Table 359 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to A~) and Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 25 4 position, Riii for a ~c...~ound corresponding to one of the groups stated in Table C
Table 360 30 Ccm~ounds of the general formula I.A (n = 0), in which UR' is ethyl~m~no, VR" is methoxy, ya is -CH2O-# (-# ~ bond to A~) and A~
i8 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 361 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 8 tated in Table C
-~ 126 2199~22 Table 362 Co".~o~nds of the general formula I.A (n o 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-~ (-# - bond to Aa) and Aa 5 is 2,5-dimethylphenyl which carries a radical CtC6H5)=NORiii in the 4 position, Riii for a oG...~vu~ld corresponding to one of the groups stated in Table C
Table 363 Compounds of the general formula I.A ~n 5 O) ~ in which UR' is methylamino,.VR" is methoxy, Y~ is -CH20-# (-# - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C~C6H5)sNORiii in the 4 position, Riii for a compound corresponding 15 to one of the groups stated in Table C
Table 364 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a coll.pound corresponding to one of the groups stated in Table C
25 Table 365 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 30 C(C6H5)=NORiii in the 4 position, Riii for a ~...pound corresponding to one of the groups stated in Table C
Table 366 35 Compounds of the general formula I.A (n 2 o), in which UR' i~
ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a cl -und corresponding to one of the groups stated in Table C
Table 367 Compounds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya i5 -CH20-# (-# = bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)=NORi~i in ~ 2199~22 the 4 position, Riii for a c~ pound corresponding to one of the groups stated in Table C
. .
Table 368 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a co,..~ound corresponding to one of the 10 groups stated in Table C
Table 369 Compounds of the general formula I.A (n = 0), in which UR' i8 15 methylamino, VR~ i8 methoxy, ya is -CH20-# (-# = bond to Aa) and ~~ Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the yL~s stated in Table C
20 Table 370 Co."p~unds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, Y~ is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORili in the 3 25 position, Riii for a compound corresponding to one of the groups stated in Table C
.
Table 371 30 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya is -CH20-~ (-* = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6Hs)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 372 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (~# ~ bond to Aa) and Aa 40 is 2-methylphenyl which carrieR a radical CtC6H5)=NORiii in the 5 position, Riii for a cor.*ol-nd corresponding to one of the groups stated in Table C
~ 219g422 128 _, Table 373 Co~ ou,~dg of the general formula I.A ~n - 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa is phenyl which carries a radical C(Cl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 374 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the g~oups stated in 15 Table C
!
Table 375 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(Cl)=NORii$ in the 4 position, Riii for a cv,.*ou~ld corresponding to one of the groups stated in Table C
25 Table 376 CG..,~oul,ds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, Y~ is -CB20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)2NORiii in the 4 30 position, Riii for a compound corresponding to one of the groups - stated in Table C
Table 377 35 C~.ll~ul~ds of the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 378 Compounds of the general formula I.A (n = 0), in which UR' i5 ethylamino, VRn i8 methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa 45 is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 2199~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 379 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)2NORiii in the 4 position, Riii for a cvn~A~ound corresponding to one of the groups 10 stated in Table C
Table 380 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VRn is methoxy, yrA is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cvA..Avv~nd corresponding to one of the groups stated in Table C
20 Table 381 Cu~ o~nds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,S-dimethylphenyl which carries a radical C(Cl)=NORiii in 25 the 4 position, Riii for a coA..A~ûund corresponding to one of the groups stated in Table C
Table 382 30 CG..,Auoullds of the general ~ormula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 383 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH2O-# (-# = bond to ArA) and 40 Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)-NORiii in the 4 position, Riii for a c~A..A~o~nd corresponding to one of the groups stated in Table C
Uu~4~u~
2199~22 Table 384 Co~ oullds of the general formula I.A (n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa 5 is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 385 Co...~o~nds of the general formula I.A (n = 0), in which UR' is methylamino,.VR" is methoxy, ya iS -cH2o-# ~-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cG...~ound corresponding to one of the 15 groups stated in Table C
f Table 386 Compounds of the general formula I.A (n = 0~, in which UR' is 20 ethylamino, VR~ i8 methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 387 CG,..poul,ds of the general formula I.A (n = 0), in which UR' i8 methylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)2NORiii in 30 the 4 position, Riii for a compound corre~ponding to one of the groups stated in Table C
Table 388 35 Cor..~ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORi~i in the 4 position, Riii for a compound corresponding to one of the ~LoU~s stated in Table C
Table 389 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and 45 Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 ~, 2199122 position, Riii for a c~".pound corresponding to one of the groups stated in Table C
Table 390 Co.,.pou~.ds of thè general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# 5 bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in 10 Table C
Table 391 Compounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and ( Aa i8 2-methylphenyl which carries a radical C(Cl)~NORiii in the 5 position, Riii for a c~r..~ou"d corresponding to one of the groups stated in Table C
20 Table 392 Compounds of the general formula I.A (n - 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 5 25 position, Riii for a cv~..poul.d corresponding to one of the groups stated in Table C
Table 393 30 Co...~o~nds of the general formula I.A (n - 0), in which UR' is methylamino, VR~ is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)~NOR1ii in the 4 position, Riii for a compound corresponding to one of the yLOU~8 stated in Table C
Table 394 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# - bond to Aa) and Aa 40 is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 395 CG~I~PO~ dS of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and 5 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cor.lp~und corresponding to one of the groups stated in Table C
Table 396 Co.l.~ou~ds of the general formula I.A (n = 0), in which UR' i8 ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiil in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
!
Table 397 Compounds of the general formula I.A (n = 0), in which UR' i8 20 methylamino, VRn is methoxy, ya i8 -CH20-# (-~ - bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co~ ound corresponding to one of the groups stated in Table C
25 Table 398 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 30 position, Riii for a compound corresponding to one of the yLVU~S
stated in Table C
Table 399 35 Compounds of the general formula I.A (n = o)~ in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to A~) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 400 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
45 is 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 ~ 2199~22 position, Riii for a ~ o~nd corresponding to one of the groups stated in Table C
Table 401 s Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# ~-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cv...~vund corresponding to one of the 10 groups stated in Table C
Table 402 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya i8 -CH20-# (-* = bond to Aa) and Aa f is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table ~03 Compounds of the general ~ormula I.A (n = 0), in which UR' is methylamino, VRn is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl whiah carries a radical 25 C(SCH3)=NORiii in the 4 position, Riii for a cv,.,~o~nd corresponding to one of the groups stated in Table C
Table 404 30 CG---~o~nds of the general formula I.A (n 5 0), in which UR' is .. ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 405 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -c~20-# (-* = bond to Aa) and 40 Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a o~...~o~nd corresponding to one of the groups 3tated in Table C
2199~22 Table 406 C~ oul~ds of the general formula I.A (n ~ 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# c bond to Aa) and Aa 5 is 2-chloro-5-methylphenyl which carries a radical C(SCH3)sNORiii in the 4 position, Riii for a cv...~ound corre~ponding to one of the groups stated in Table C
Table 407 Compounds of the general formula I.A (n = 0), in which.UR' is methylamino,.VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
Table 408 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, R~ii for a compound corresponding to one of the groups stated in Table C
25 Table 409 Co~ ounds of the general formula I.A (n = 0), in which UR' is methylamino ~ VRn iB methoxy, ya is -CH20 - ~ ( ~# Q bond to Aa) and Aa is phenyl which carries a radical C(SCH3)-NORiii in the 3 30 positionr Riii for a co...~oulld corresponding to one of the ~ou~s - stated in Table C
Table 410 35 Compounds of the general formula I.A (n - o)~ in which UR' i8 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 411 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 219g~22 5 position, Riii for a c _~ul~d corresponding to one of the y ou~s stated in Table C
Table 412 Compounds of the general formula I.A (n = O), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)'NORiii in the 5 position, Riii for a c~po-~d corresponding to one of the groups 10 stated in Table C
Table 413 Compounds of the general formula I.A (n = O), in which UR' is 15 methylamino, VRn is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carrie~ a radical C(cyalopropyl)~NOR~ii in the 4 position, Riii for a cG.,.~ou.ld corresponding to one of the groups stated in Table C
20 Table 414 Co...p~ul,ds of the general for~ I.A (n = O), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and A~
is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 25 position, Riii for a cv~ ound corresponding to one of the y~S
stated in Table C
Table 415 30 ~ -unds of the general formula I.A (n = O), in which UR' is methylamino, VR" i8 methoxy, ya iS -CH20-$ (-# ~ bond to Aa) and Aa i5 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a ~c...~ound corresponding to one of the groups stated in Table C
Table 416 Compounds of the general formula I.A (n = O), in which UR' is ethylamino, VR is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa 40 is 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
219g~22 Table 417 Compounds of the general formtll~ I.A (n = 0), in which UR' is methylamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and 5 Aa i8 2-fluorophenyl which carries a radical C(cyclopropyl)=NOR
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 418 Compounds of the general formula I.A (n = 0), in which UR' i5 ethylamino, V.R~' is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and A~
is 2-fluorophenyl which carries a radical c(cyclopropyl)=NoRiii in the 4 position, Riii for a cG~ d corresponding to one of the 15 groups stated in Table C
f Table 419 Co..l~ounds of the general form~ I.A (n = 0), in which UR' is 20 methylamino, VR" is methoxy, ya iS -CH20-# (-# - bond to A~1 and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 420 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~
i8 2-chlorophenyl which carries a radical C(cyclopropyl)-NOR~ii in 30 the 4 position, Riii for a compound corresponding to one of the - groups stated in Table C
Table 421 35 C~r~.~Gunds of the general formula I.A (n - 0), in which UR' i8 methylamino, VR" is methoxy, ya is -CH20-~ (-# 3 bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical ~
C(cyclopropyl)=NORiii in the 4 position, Riii for a ~v.l*o~l.d corresponding to one of the y-OU~S stated in Table C
Table 422 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to A~) and Aa 45 is 2,5-dimethylphenyl which carries a radical 2l99~22 C(cyclopropyl)=NORiii in the 4 position, Riii for a c _u~ld corresponding to one of the groups stated in Table C
Table 423 Coh.~ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a co...~Gu~.d 10 corresponding to one of the groups stated in Table C
Table 424 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa ! is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 po~ition, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 425 C.~ oullds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chlo~o 5 methylphenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 position, Riii for a cGI..~Gund corresponding to one of the groups stated in Table C
Table 426 30 Compounds of the general formula I.A (n = 0), in which UR' is f ethylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv,.lpound corresponding to one of the groups stated in Table C
Table 427 Co..l~ounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ = bond to Aa) and 40 Aa is 2,S-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Rii~ for a compound corresponding to one of the groups stated in Table C
2199~22 Table 428 Compounds of the general formula I.A (n ~ 0), in which UR' i8 ethylamino, VR" is methoxy, ya is -CH20-~ (-# 5 bond to Aa) and Aa 5 is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)-NORiii in the 4 po~ition, Riii for a ~ ound corresponding to one of the groups stated in Table C
Table 429 Cv...pGunds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya is -CH20-~ bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORlii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 430 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 431 CG.-~ounds of the general formula I.A (n c 0)~ in which UR' is methylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii 30 in the 5 position, Riii for a c~l..~Gund corresponding to one of the groups stated in Table C
.~
Table 432 35 CGLI-pvunds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 433 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ 5 bond to Aa) and 45 Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 _ ~ 139 2199~22 position, Riii for a-compound corresponding to one of the y~ups stated in Table C
Ta~le 434 s Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a coh.~und corresponding to one of the groups stated in 10 Table C
Table 435 C~,..pounds of the general formula I.A (n = 0), in which UR' is 15 methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and I Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 436 CG...pounds of the general formula I.A (n = 0), in which UR' i~
ethylamino, VR" i8 methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-methylphenyl which carrie~ a radical C(CF3)=NORLii in the 4 25 position, Riii for a cG..~ou~ld corresponding to one of the groups stated in Table C
Table 437 30 CoAI-pG~nds of the general formula I.A (n = 0), in which UR' is r methylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y-OU~5 stated in Table C
Table 438 Compounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-fluorophenyl which carries a radical C~CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
140 2199~22 Table 439 Co...~ullds of the general formula I.A (n e 0)~ in which UR' is methylamino, VR" is methoxy, ya i~ -CH20~ = bond to Aa) and 5 Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 440 Compounds of the general formula I.A (n = 0), in which UR' i8 ethylamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv...~ound corresponding to one of the group 15 stated in Table C
f Table 441 Compounds of the general formula I.A (n = 0), in which UR' is 20 methylamlno, VR" i8 methoxy, Y4 i8 -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups ~tated in Table C
25 Table 442 Co.l~you.lds of the general formula I.A (n = 0), in which UR' i~
ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the ~.ou~s r stated in Table C
Table 443 35 CG..~u..ds of the general formula I.A (n = 0), in which UR' i8 methylamino, VRn is methoxy, Y~ is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv...~oul~d corresponding to one of the groups stated in Table C
Table 444 CGr~l~o~nds of the general formula I.A (n = 0), in which UR' is ethylamino, VRn is methoxy, ya is -CH20-~ (-X = bond to Aa) and Aa 45 is 2-methyl-5-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cv.,.pound corresponding to one of the groups stated in Table C
Table 445 Compounds of the general formula I.A (n = 0), in which UR' is methylamino, VR" i5 methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Rili for a cvm~G~l-d corresponding 10 to one of the groups stated in Table C
Table 446 Compounds of the general formula I.A (n = 0), in which UR' is lS ethylamino, VR is methoxy, ya i5 -CH20-~ (-# = bond to A~) and Aa f is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NOR~ii in the 4 position, Riii for a c~."poulld corresponding to one of the groups stated in Table C
20 Table 447 CG",POUndS of the general formula I.A (n = 0), in which UR' is methylamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 448 30 CG...~ounds of the general formula I.A (n = 0), in which UR' is ethylamino, VR" i8 methoxy, ya is -CH20-# (-# = bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 449 Compounds of the general formula I.A (n = 0), in which UR' i~
methylamino, VR" is methoxy, ya iS -CH20-# (~~ = bond to Aa) and 40 Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a co."po~id corresponding to one of the groups stated in Table C
Table 450 Compounds of the ~eneral formula I.A (n = 0), in which UR' is ethylamino, VR" is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa 5 is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 451 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methylamino, VR" i8 methoxy, ya iS -CH20-# (-# = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CF3)-NORiii in the 5 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 452 Compounds of the general formula I.A (n = 0), in which UR' i8 20 ethylamino, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and A~
is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 453 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, 30 Riii for a ~ -u~.d corresponding to one of the groups stated in r Table C
~, Table 454 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# z bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 455 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-# (-~ - bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 2I99~22 position, Riii for a c~ ou"d corresponding to one of the groups stated in Table C
Table 456 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a ~v~..~o~nd corresponding to one of the groups 10 stated in Table C
Table 457 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VRn is methylamino, ya is -CHzO-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a co...~Gul.d corresponding to one of the groups stated in Table C
20 Table 458 CGl,.~Gunds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CH=NORiii in the 4 25 position, Riii for a co...pG~nd corresponding to one of the groups stated in Table C
Table 459 30 Compounds of the general formula I.A (n = 0), in which UR' is - methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa $s 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 460 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-chlorophenyl which carries a radical CHsNORiii in the 4 position, Riii for a c~...pGund corresponding to one of the groups stated in Table C
Table 461 Co~ oullds of the general formula I.A (n ~ 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-$ = bond to Aa) and 5 Aa is 2,5-dimethylphenyl which carries a radical CH=NOR~ii in the 4 position, Riii for a co..l~ound corresponding to one of the ~-u~s stated in Table C
Table 462 Compounds of the general formula I.A (n = 0), in which UR' is ethûxy, VR" is methylamino, ya is -CH2O-~ (-# = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
f Table 463 Compounds of the general formula I.A (n - 0), in which UR' i8 20 methoxy, VR" is methylamino, ya is - CH20-# t-# 2 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 464 CGr~.poul,ds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH2o-$ (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carrie~ a radical CH=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the -- groups stated in Table C
Table 465 35 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -CH20-# (-~ 5 bond to Aa) and Aa i8 2-chloro-S-methylphenyl which carries a radical CH=NORiii ~n the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 466 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20~ 2 bond to Aa) and Aa 45 is 2-chloLo 5 methylphenyl which carries a radical CH2NO~iii in - ' ~
14.5 2199~22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 467 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methyla~ino, ya i8 -CH20~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH-~ORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 468 Compounds of the general formula I.A (n 5 0), in which UR' is 15 ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa r is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~ 20 Table 469 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya i8 -CH20-# (-~ 8 bond to A~) and Aa is phenyl which carries a radical CH=NORiii in the 3 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 470 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-# (-~ = bond to A~) and Aa is phenyl which carries a radical CHsNORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 471 Co~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ ~-# = bond to Aa) and 40 Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
.
0050~45204 Table 472 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# 5 bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical CH-NORiii in the 5 position, Riii for a co,l,~o~nd corresponding to one of the groups stated in Table C
Table 473 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' .
Table 474 Col.*o~l,ds of the general formula I.A (n = 0), in which UR' i8 20 ethoxy, VR" i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 47~
Compounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya i5 -C~20-~ (-$ ~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups , stated in Table C
Table 476 35 Compounds of the general formula I.A (n 2 O) r in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)~NORiii in the 4 position, Riii for a compound corresponding to onè of the groups stated in Table C
Table 477 Compounds of the general formula I.A (n 2 O) r in which UR' is methoxy, VR" is methylamino, yA is -CH20-~ = bond to Aa) and 45 Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the ~50~4S~U4 219~922 4 position, Riii for a cv~..pound corresponding to one of the groups stated in Table C
Table 478 Co...~ourlds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a c~ ound corresponding to one of the groups 10 stated in Table c Table 479 Compounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methylamino, Y~ i8 -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a cG.,.~ou~d corresponding to one of the groups stated in Table C
20 Table 480 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH2O-# (-~ = bond to Aa) and A~
is 2-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 481 30 CGll.~ounds of the general formula I.A (n = 0), in which UR' is f methoxy, VR" is methylamino, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical CtCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table c Table 482 Co.ll~ourlds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-~ = bond to Aa) and Aa 40 is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the yLO~S
stated in Table C
005~/45204 148 2199~22 Table 483 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" is methylamino, ya i8 -CH20-# ~-# = bond to Aa) and 5 Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 484 Cu...pG~ds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR~' is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH3)=NORii~
in the 4 position, Riii for a c~ ound corresponding to one of the 15 groups stated in Table C
Table 485 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VRN is methylamino, ya i8 -CH20-~ (-# = bond to A~) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a CVA.~ Id corresponding to one of the groups stated in Table C
25 Table 486 C- ,ou~lds of the general form~ I.A ~n 5 O) ~ in which UR' is ethoxy, VRn is methylamino, Y~ is -CH20-# (-# = bond to Aa) and Aa is 2-chloLo 5 -thylphenyl which carries a radical C(CH3)=NORiii 30 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 487 3S Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a co...~o~nd corresponding to one of the groups stated in Table C
Table-488 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
45 is 2,5-dichlorophenyl which carries a radical C(CB3)=NORiii in the 2199~22 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 489 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa i8 phenyl which carries a radical CtCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 490 . ~.~
Co~ oul,ds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, Y~ is -CH2O-# (-# 5 bond to Aa) and Aa f is phenyl which carries a radical C(CH3)-NORili in the 3 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
20 Table 491 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH3)-NORiii in the 25 5 position, Riii for a ~~oLI~o~.d corresponding to one of the groups stated in Table C ~.
", . . .
Table 492 30 Compounds of the general formula I.A (n = O), in which UR' is f ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
~. is 2-methylphenyl which carries a radical C(CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 493 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-# - bond to Aa) and 40 A~ i8 phenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a c~mpound correspo~ding to one of the groups stated in Table C
~ 2199 122 Table 494 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# ~ bond to Aa) and AA
5 is phenyl which carries a radical C(CH2CH3)~NORi~i in the 4 position, Riii for a compound corresponding to one of the y- OU~8 stated in Table C
Table 495 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR".is methylamino, ya iS -CH20-~ (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
' Table 4g6 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, Y~ is -CH20-~ (-# = bond to A~) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)~NORili in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 497 Compounds of the general formula I.A (n = 0), in which UR' i~
methoxy, VR is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a ~ ound corresponding to one of the groups stated in Table C
Table 498 35 C~ -o~ ds of the general formula I.A (n - 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and A~
is 2-fluorophenyl which carries a radical C(CH2CH3)-NORii~ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 499 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya iS -CH20-# (-# = bond to Aa) and 45 Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in ~ /45~4 ~ 151 2199 1 22 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 500 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cor..p~u~,d corresponding to one of the groups lO stated in Table C
Table 501 Cu..,~ounds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" is methylamino, ya is -CH2O-~ s bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 502 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR i8 methylamino, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in 25 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 503 30 Compounds of the general formula I.A (n 8 O) ~ in which UR' is methoxy, VRn is methylamino, ya i~ -CH2O-# (-# = bond to Aa) and f Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 504 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH2O-~ (-# = bond to A~) and Aa 40 is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a com~und corresponding to one of the groups stated in Table C
2199~22 Table 505 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methyl A~ no~ ya is -CH20-# (-# = bond to Aa) and 5 Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 506 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, yn is -CH20-# (-# = bond to Aa) and Aa i~ 2-chloro-5-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a .G~ und 15 corresponding to one of the groups stated in Table C
Table 507 C~...pou,lds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methylamino, ya is -CH20-# (-~ 5 bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a ~o,~.pouI,d corresponding to one of the groups stated in Table C
25 Table 508 C~..pounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya iS -CH20-~ (-# = bond to Aa) and A~
is 2,5-dichlorophenyl which carries a radical C(CH2CH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the . groups stated in Table C
Table 509 35 Co...~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methyl~mino, ya is -CH20-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 position, Riii for a col.,~ound corresponding to one of the groups stated in Table C
Table 510 Co...~oullds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR~ is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 45 is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 153 2 1 g 9 ~ 2 2 position, Riii for a-co~ nd corresponding to one of the ~LO~S
stated in Table C
.
Table 511 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a c~".~ound corresponding to one of the 10 groups stated in Table C
Table 512 C~ ounds of the general formula I.A (n z 0), in which UR' is 15 ethoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and Aa f is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 513 C~-..~ounds of the general for~~ I.A (n 2 O) ~ in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORli~ in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 514 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 515 CG...~ounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya iS -CH20-~ = bond to Aa) and 40 Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ ourld corresponding to one of the groups stated in Table C
.
~ ~19912~
Table S16 Co...~o~l~ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa 5 is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ oul~d corresponding to one of the y.uu~S stated in Table C
Table 517 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR".is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORii~ in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
( Table 518 Compounds of the general formula I.A (n 3 O) ~ in which UR' i8 20 ethoxy, VR" i8 methylamino, ya iS - CH20-~ (~# e bond to Aa) and AA
is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound correspon~;~g to one of the groups stated in Table C
25 Table 519 CG...~ul.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in 30 the 4 position, Riii for a cG,..~o~"d corresponding to one of the group~ stated in Table C
. .
Table 520 35 Compounds of the general formula I.A (n = 0), in which UR' i5 ethoxy, VR" i8 methylamino, ya is -CH20-# (-~ - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 521 Compounds of the qeneral formula I.A (n = 0), in which UR~ is methoxy, VR" is methylamino, ya is -CH20-# (-# 2 bond to Aa) and 45 Aa is 2,5-dimethylphenyl which carries a radical .
UU~U~ 4~U~
2199~22 CtCH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 522 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CHzCH2CH3)=NORiii in the 4 position, Rlii for a compound corresponding to one of the 10 groups stated in Table C
Table 523 Co~ ou,~ds of the general formula I.A (n = 0), in which UR' is 15 methoxy, VR" i8 methylamino, ya is -CH20-# (-# = bond to Aa) and f~ A~ is 2-methyl-5-chlorophenyl which carrie~ a radical - C(CH2CH2CH3)=NORlii in the 4 posit~on, Riii for a cv.,.~und corresponding to one of the groups stated in Table C
20 Table 524 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 25 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv,.,~vund corresponding to one of the groups stated in Table C
Table 525 30 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv...~o~r.d corresponding to one of the groups stated in Table C
Table 526 Cv.ll~ounds of the general formula I.A (n = 0), in~which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 40 is 2-chloro-5-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cv...~nd corresponding to one of the groups stated in Table C
OU50/4S~4 2~99~22 Table 527 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, yn iS -CH20-# (-# = bond to Aa) and S Aa i8 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a c~ o~lld corresponding to one of the groups stated in Table C
Table 528 Compounds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya i9 -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH2CH3)=NORlii in the 4 position, Riii for a compound corresponding to one of the 15 y~OU~S stated in Table C
Table 529 Cu...~u~ds of the general formula I.A (n - 0), in which UR~ i3 20 methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a co.,.~ou.d corresponding to one of the groups stated in Table C
25 Table 530 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 30 position, Riii for a cu~ ou..d corresponding to one of the y ~s stated in Table C
Table 531 35 Compounds of the general formula I.A (n ~ 0), in which UR' i8 methoxy, VR" is methylamino, ya iS -CH20-~ 5 bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a c~ ound corresponding to one of the y r o~s stated in Table C
Table 532 Cull.~ou,lds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, Y~ is -CH20-# (-~ - bond to Aa) and Aa 45 is 2-methylphenyl which carries a radical C(CH2CH2CH3)sNORili in 2~99 122 the 5 position, Riii for a c~ u--d corresponding to one of the groups stated in Table C
Table 533 Cu..*ou.,dg of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" is methylamino, ya is -CH20-# (-# z bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in the 4 position, Riii for a ov,..~ulld corresponding to one of the ~- uU~8 10 stated in Table C
Table 534 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa ! i8 phenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a cou.~ d corresponding to one of the yLOU~S
stated in Table C
20 Table 535 Co~ oul~ds of the general formula I.A (n - 0), in which UR' is methoxy, VRn is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=N0Riii in 25 the 4 position, Riii for a co"~und corresponding to one of the groups stated in Table C
Table 536 30 Compounds of the general formula I.A (n 2 0)~ in which UR' is {- ethoxy, VR" is methylamino, ya i5 -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a cv".~ound corresponding to one of the groups stated in Table C
Table 537 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20~ = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical CtCH(CH3)2]=NORiii in the 4 position, Ri~i for a cvl..~oulld corresponding to one of the groups stated in Table C
Table 538 CG1..~0UndS of the general formula I.A (n - O), in which UR' i9 ethoxy, VR" is methylamino, Y~ is -cH2o-# (-~ - bond to Aa) and Aa 5 is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NOR~ii in the 4 position, Riii for a co,.,~ound corresponding to one of the groups stated in Table C
Table 539 Co,..~ou.lds of the general fo~mlll? I.A (n - O), in which UR' is methoxy, VR".is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-chlorophenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a cv,.l~ound corresponding to one of the 15 groups stated in Table C
Table 540 Compounds of the general formula I.A (n ~ O), in which UR' is 20 ethoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C[CH(CH3)z]=NORiii in the 4 position, Riii for a c~ G~nd corresponding to one of the groups stated in Table C
25 Table 541 Com~ounds of the general formula I.A (n e O) ~ in which UR' is methoxy, VR" i8 methylamino, ya iS -CH20~ bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3)2]=NOR
30 in the 4 position, Riii for a compound corresponding to one of the oups stated in Table C
Table 542 35 Compounds of the general formula I.A tn = O), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C[CH(CH3) 2 ] =NOR~ii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 543 Compounds of the general formula I.A (n = O), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and 45 Aa is 2-methyl-5-chlorophenyl which carries a radical ClCH(CH3)2]=NORiii in the 4 position, Ri~i for a co,..~o~lld corresponding to one of the groups stated in Table C
Table 544 Co~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i9 methylamino, ya iS -CH20-# (-~ z bond to Aa) and A' i8 2-methyl-5-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a cv,.*o~nd 10 corresponding to one of the groups stated in Table C
Table 545 Co,.*oul~ds of the general formula I.A (n - 0), in which UR' is lS methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and ( Aa is 2-chloro-5-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the ylo~s stated in Table C
20 Table 546 CG,--~o~uds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya i8 -CH20-~ (-# = bond to Aa) and Aa is 2-chloro-5-~ethylphenyl which carries a radical 25 C[CH(CH3)2]2NORiii in the 4 position, Riii for a c~ ~und corresponding to one of the yLOup~ stated in Table C
Table 547 30 Compounds of the general formula I.A (n = 0), in which UR' is ~-- methoxy, VRn is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C~CH(CH3)2]=NORi~i in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 548 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# z bond to Aa) and A~
40 is 2,5-dichlorophenyl which carries a radical C[CH(CH3)2]zNORiii in the 4 position, Rili for a COI oul~d corresponding to one of the groups stated in Table C
2193~22 Table 549 Co..,~oul~ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH2O-# (-# - bond to Aa) and 5 Aa i5 phenyl which carries a radical C~CH(CH3) 2 ]=NORiii in the 3 position, Riii for a c~l"pound corresponding to one of the groups stated in Table C
Table 550 Co~ ou.,ds of the general form~ I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-~ = bond to Aa) and Aa is phenyl which carrie~ a radical CtCH(CH3)2~=NORiii in the 3 position, Riii for a compound corresponding to one of the yL~U~
15 stated in Table C
(~
Table 551 Compounds of the general formula I.A (n - 0), in which UR' i8 20 methoxy, VR" is methylamino, ya i8 -CH2O-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C~CH(CH3) 2 ]=NORiii in the 5 position, Riii for a co...~und corresponding to one of the yLUU~S stated in Table C
25 Table 552 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamlno, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3) 2 ]=NORiii in 30 the 5 position, Riii for a ~c..~ound corresponding to one of the groups stated in Table C
Table 553 35 Compounds of the general formula I.A (n 5 O) ~ in which UR' is methoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 554 Compounds of the general formula I.A (n - 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH20-# ( ~~ 5 bond to Aa) and Aa 45 is phenyl which carries a radical C(C6H5)=NOR~i~ in the 4 --0050/45204 2 1 9 g '1 2 2 position! Riii for a cc...y~und corresponding to one of the g-ou~s stated in Table C
Table 555 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# t-~ s bond to Aa) and An is 2-methylphenyl which carries a radical C(C6Hs)=NORili in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 556 Compounds of the general formula I.A (n - 0), in which UR' i8 15 ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a compound corresponding to one of the y GU~S
stated in Table C
20 Table 557 CG...~ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6H5)=NORi~i in the 25 4 position, Riii for a c _ou"d corresponding to one of the groups stated in Table C
Table 558 30 Compounds of the general formula I.A (n = 0), in which UR' i8 ~- ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa ~ is 2-fluorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 559 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
0050/,5204 2 1 9 9 1 2 2 Table 560 Compounds of the general formula I.A (n o 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and Aa 5 is 2-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 561 Co".~G~,lds of the general formula I.A (n = 0), in which UR' i8 methoxy, VR".is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(C6H5)-NORiii in the 4 position, Riii for a ~v...~ound corresponding to one of the 15 groups stated in Table C
f Table 562 Compounds of the general formula I.A (n 2 O) ~ in which UR' is 20 ethoxy, VR" is methylamino, ya iY -CH20~ # = bond to Aa) and A~
i8 2,5-dimethylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 563 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# 5 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 C(C6H5)sNORiii in the 4 position, Riii for a c~..pGund corresponding to one of the groups stated in Table C
.
Table 564 35 Cu.,.~o~nds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# 2 bond to Aa) and Aa is 2-~ethyl-5-chlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 565 Compounds of the ~eneral formula I.A (n = 0), in which UR' i~
methoxy, VR" is methylamino, ya iS -CH20-# (-~ e bond to Aa) and 45 Aa is 2-chloro-5-~ethylphenyl which carries a radical ~ 2199~22 C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 566 s Compounds of the general formula I.A (n = O), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a co,..~o~.,d corresponding to one of the 10 groups stated in Table C
Table 567 Compounds of the general formula I.A (n = O), in which UR' is 15 methoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and ! . Aa is 2,5-dichlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 568 Compounds of the general formula I.A (n - O), in which UR' is ethoxy, VR" i8 methylamino, ya iS -CH20-# (-# - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in 25 the 4 position, Riii for a cor,.~ohnd corresponding to one of the groups stated in Table C
Table 569 30 Compounds of the general formula I.A (n = O), in which UR' is r methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 3 position, Riii for a compound corresponding to one of the y O~B
stated in Table c Table 570 Co~ vunds of the general formula I.A (n = O), in which UR' iB
ethoxy, VR" is methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa 40 is phenyl which carries a radical C(C6H5)=NOR~ii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
00~0/45204 ~ 2199~22 Table 571 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-# (-# = bond to Aa) and S A~ is 2-methylphenyl which carriQs a radical C(C6H5)-NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 572 C~ oul,ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i.s methylamino, ya iS -CH20~ = bond to A~) and Aa is 2-methylphenyl which carries a radical C~C6Hs)-NORili in the 5 position, Riii for a compound corresponding to one of the yLO~
15 stated in Ta~le C
¢'.
Table 573 Cu.l*ounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR is methylamino, Y~ is -CH20-# (-~ = bond to AA) and Aa is phenyl which carries a radical C(Cl)~NORiii in the 4 position, Riii for a compound corresponding to one of the yLOU~S
stated in Table C
25 Table 574 Compounds of the general formula I.A (n 5 O) ~ in which UR' is ethoxy, VR" i~ methylamino, ya iS -CH20-# (-# ~ bond to Aa) and A~
i8 phenyl which carries a radical C(Cl)=NORiii in the 4 position, 30 Riii for a compound corresponding to one of the yrO~p~ stated in f Table C
Table 575 35 Compounds of the general formula I.A (n = o)r in which UR' is methoxy, VR" is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(Cl)=NORi~i in the 4 position, Riii for a compound corresponding to one of the y r O~pS
stated in Table C
Table 576 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and A~
45 is 2-methylphenyl which carries a radical C(Cl)=NORi~i in the 4 OU50~452~4 ~ 2199~22 position, Riii for a compound corresponding to one of the ylOu~
stated in Table C
Table 577 Compounds of the general formula I.A (n 5 0)~ in which UR' is methoxy, VR~' is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(Cl)sNORiii in the 4 position, Riii for a cv...~ound corresponding to one of the groups 10 stated in Table C
Table 578 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and Aa (' i8 2-fluorophenyl which carrie~ a radical C(Cl)=NORili in the 4 position, Riii for a cc...~ound corresponding to one of the groups stated in Table C
20 Table 579 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 25 position, Riii for a co...~v~nd corresponding to one of the yLOU~S
stated in Table C
Table 580 30 Cor.-~ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i5 methylamino, ya is - C~20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~5 Table 581 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# ( -# 5 bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(Cl)zNORiii in the 4 position, Ri~i for a cv..,po~nd corresponding to one of the yLOu~S stated in Table C
~able 582 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20~ 5 bond to Aa) and Aa 5 is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, R~ii for a c~ oulld corresponding to one of the groups stated in Table C
Table 583 C~ o~nds of the general formula I.A (n = 0), in which UR' i9 methoxy, VR" is methylamino, ya iS -CH20~ 5 bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a cvmpound corresponding to one of the 15 groups stated in Table C
Table 584 Cu...~ul~ds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a c~ o~.d corresponding to one of the groups stated in Table C
25 Table 585 Co.--~v~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii 30 in the 4 position, Riii for a cv...~ound corresponding to one of the f~ groups stated in Table C
_ Table 586 35 Compounds of the general formula I.A (n 5 0), in which UR' is ethoxy, VR" is methylamino, ya iS - CH20-# ( -~ 5 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 587 Compounds of the general formtll~ I.A (n = 0), in which UR' is methoxy, VR" is methylamino, Y~ is -CH20-# (-~ = bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in , U~/4~4 2199~2~
the 4 position, Riii for a co~ ound corresponding to one of the groups stated in Table C
Table 588 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a co".~oulld corresponding to one of the groups 10 stated in Table C
Table 589 Compounds of the general formula I.A (n = 0), in which UR' is lS methoxy, VR" is methylamino, Y~ i8 -CH20-# (-~ = bond to Aa) and f A~ is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a c~",~oulld corresponding to one of the groups stated in Table C
20 Table 590 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(Cl)sNORiii in the 3 position, 25 Riii for a compound corresponding to one of the groups stated in Table C
Table 591 30 Compounds of the general formula I.A (n = 0), in which UR' i5 ~- methoxy, VR" is methylamino, ya iS - CH20-~ 5 bond to Aa) and Aa is 2-methylphenyl which carrie~ a radical C(Cl)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 592 Compounds of the general formula I.A (n = 0), in'which UR' is ethoxy, VRn is methylamino, ya iS -cH2o-# (-~ = bond to Aa) and Aa 40 is 2-methylphenyl which carries a radical C(Cl)2NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
~ = ==
2199~22 Table 593 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" i8 methylamino, ya iS -CH20-# (-# = bond to Aa) and 5 Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 594 Compounds of the general formula I.A (n e ~)r in which UR~ i5 ethoxy, VR i8 methylamino, ya iS -CH20-~ (-# e bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cv..,poul.d corresponding to one of the groups 15 stated in Table C
~, Table 595 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methyl pm~ not ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a cGr~ und corresponding to one of the groups stated in Table C
25 Table 596 C o~l~ds of the general for~ I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-~ = bond to Aa) and A~
is 2-methylphenyl which carrie~ a radical C(SCH3)~NORiii in the 4 30 position, Riii for a .~G~ o~nd corresponding to one of the groups stated in Table C
Table 597 35 Compounds of the general formula I.A (n = 0), in which UR' i5 methoxy, VR" i5 methylamino, ya i8 -CH20-# (-~ = bond to Aa) and A~ is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 598 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya i8 -CH20-~ (-# = ~ond to A~) and Aa 45 is 2-fluorophenyl which carries a radical C(SCH3)=NORiii in the 4 2199~22 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 599 Cc..~p~ul.ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i~ -CH2O-# (-# = bond to Aa) and A~ i8 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y.OU~S
10 stated in Table C
Table 600 Co.~ unds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR" is methylamino, ya iS -CH20-# (-$ - bond to Aa) and Aa ~' iY 2-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a c~r..~ound corresponding to one of the groups stated in Table C
20 Table 601 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR i8 methylamino, ya is -CH20-# (-# z bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)=NORiii in ~5 the 4 position, Riii for a compound corresponding to one of the g~uups stated in Table C
Table 602 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya iS -CH2O-# (-~ = bond to Aa) and A~
is 2,5-dimethylphenyl which carries a radical C(SCH3)=NOR~ii in the 4 position, Riii for a c~ ound corresponding to one of the groups stated in Table C
Table 603 C~ ounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~' is methylamino, ya iS -CH2O-# (-# = bond to Aa) and 40 A~ is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Rii~ for a cv~.~oui,d corresponding to one of the groups stated in Table C
~050/45204 2199~22 Table 604 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa 5 is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co.,~pou.~d corresponding to one of the groups stated in Table C
Table 605 Compounds of the general formula I.A (n - 0), in which ~R' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)-NORiii in the 4 position, Riii for a ~o-..pou,.d corresponding 15 to one of the groups stated in Table C
Table 606 Cum~ounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(SCH3)~NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 607 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR is methylamino, ya i~ -CH20-# (-~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f groups stated in Table C
., Table 608 35 C~..,poullds of the general formula I.A (n = 0), in which UR' i8 ethoxy, VR" is methylamino, ya iS -CH2O-# (-# = bond to Aa) and A~
is 2,5-dichlorophenyl which carries a radical C(~CH3)=NORiii in the 4 position, Riil for a c~...pound corresponding to one of the groups stated in Table C
Table 609 CG,..~o~nds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and 45 Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a cv..,~ound corresponding to one of the groups stated in Table C
Table 610 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# t-# ~ bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 611 Cor~o~..ds of the general formula I.A (n - 0), in which UR~ is 15 methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to A~) and ' Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 position, Riii for a ov~ o~nd corresponding to one of the ~o~s stated in Table C
.
20 Table 612 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya i8 -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 5 25 position, Riii for a co,..p~und corresponding to one of the y~u~S
stated in Table C
Table 613 30 Compounds of the general formula I.A (n = 0), in which UR' i8 f methoxy, VR" is methylamino, yn is -CH20-# (-~ = bond to Aa) and A~ is phenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cv~ ound corresponding to one of the groups stated in Table C
Table 614 Compounds of the general formula I.A (n = 0), in which UR ' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa 40 is phenyl which carries a radical c(cyclo~ro~yl)=NoRiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
00~0/45204 219g422 Table 615 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# s bond to A~) and 5 Aa is 2-methylphenyl which carries a radical C(cyclopropyl)-NORiii in the 4 position, Riii for a co.~,~ou~-d corresponding to one of the yL~U~S stated in Table C
Table 616 C~",~o~nds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a c~ o~lld corresponding to one of the 15 groups stated in Table C
Table 617 Compounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" i8 methylamino, ya is -CH20-~ (-# 5 bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiil in the 4 position, Rili for a ov~ o~nd corresponding to one of the groups stated in Table C
25 Table 618 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ 2 bond to A~) and Aa is 2-fluorophenyl which carries a radical C(cyclopropyl)=NORiii in 30 the 4 position, Riii for a compound corresponding to one of the f yLGUyS stated in Table C
,, ~
Table 619 35 CoL.~oullds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cG..~pound corresponding to one of the yLoups stated in Table C
Table 620 Compounds of the general formula I.A (n = o)~ in which UR~ is ethoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and A~
45 is 2-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in 0050/45204 2 1 9 ~ l 2 2 the 4 position, Riii for a-~o~ ou.ld corresponding to one of the groups stated in Table C
Table 621 Compounds of the general formula I.A (n - 0), in which UR' i8 methoxy, VR" i8 methylamino, ya is -CH20-# ( -# 2 bond to Aa) and Aa i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound 10 corresponding to one of the ~L0~8 stated in Table C
Table 622 Cul,-~ounds of the general formula I.A (n = 0), in which UR' i8 15 ethoxy, VR is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa i8 2,5-dimethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a cvl.-~o~nd corresponding to one of the groups stated in Table C
20 Table 623 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VRn is methylamino, ya iS -CH20-~ (-# = bond to Aa) and Aa i5 2-methyl-5-chlorophenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 pO8 ition, Riii for a cG~ ound corresponding to one of the groups stated in Table C
Table 624 30 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -cH2o-# (-~ - bond to Aa) and An is 2-methyl-5-chlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a co".~ound corresponding to one of the y~u~s stated in Table C
Table 625 Compounds of the general formula I.A (n = 0), in which UR~ is methoxy, VR~ is methylamino, ya is -cH2o-# (-~ = bond to Aa) and 40 Aa is 2-chloro-5-~ethylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
u~ 4~
219~22 Table 626 Co..,~ul.ds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa 5 i8 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 627 Co~ ourlds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii for a compound 15 corresponding to one of the groups stated in Table C
Table 628 Compounds of the general formula I.A (n = 0), in which UR' is 20 ethoxy, VRn is methylamino, ya i8 -CH20~ bond to A~) and Aa is 2,5-dichlorophenyl which carries a radical C(cycloplo~yl)=NoRiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 629 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR~ is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 30 3 position, Riii for a compound corresponding to one of the groups f stated in Table C
Table 630 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a compound corresponding to onè of the ~LOU~8 stated in Table C
Table 631 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya i5 -CH20-# (-~ = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NOR
~U/4~
in the 5 position, Riii for a cvr,,~ound corresponding to one of the groups stated in Table C
Table 632 CGm~oullds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORi~i in the 5 position, Riii for a c~m~ound corresponding to one of the 10 groups stated in Table C
Table 633 CG",~ounds of the general formula I.A (n = 0), in which UR' is lS methoxy, VR" is methylamino, ya is -CH2O-# (-# = bond to Aa) and ( A~ i8 phenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a ~o."~ound corresponding to one of the groups stated in Table C
20 Table 634 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 4 position, 25 Riii for a cv,,,~ou.ld corresponding to one of the ~ou~s stated in Table C
Table 635 30 Compounds of the general formula I.A (n - 0), in which UR' i5 methoxy, VRn is methylamino, Y~ is -CH2O-~ (-# 8 bond to A~) and ~ A~ i3 2-methylphenyl which carries a radical C(CF3)=NoRi~$ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 636 Compounds of the general formula I.A (n = 0), in 'which UR' is ethoxy, VR" is methylamino, ya is -CH2O-~ = bond to Aa) and A~
40 is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a c~ poul,d corresponding to one of the yLou~s stated in Table C
4~
Table 63~ -Co.,.~ounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20~ # = bond to Aa) and 5 Aa is 2-fluorophenyl which carries a radical C(CF3)sNORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 638 CG~ ounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" i8 methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
~' Table 639 Col,.~,ounds of the general formula I.A (n = 0), in which UR' is 20 methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the y-vU~S
stated in Table C
25 Table 640 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CF3)=NORiii in the 4 30 position, Riii for a compound corresponding to one of the groups ~- stated in Table C
., Table 641 35 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a cr oulld corresponding to one of the groups stated in Table C
Table 642 Cv~ ou..ds of the general formula I.A (n = 0), in which UR' i~
ethoxy, VR" is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa 45 is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the ~199422 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 643 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR~ is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical CtCF3)=NORiii in the 4 position, Riii for a compound corresponding 10 to one of the groups stated in Table C
Table 644 Compounds of the general formula I.A (n = 0), in which UR' is 15 ethoxy, VR~ is methylamino, ya is -CH20-~ ( -# 3 bond to Aa) and Aa ( is 2-methyl-5-chlorophenyl which carries a radical C(CF3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 645 Compounds of the general formula I.A (n - 0), in which UR' is methoxy, VR" is methylamino, ya i8 -CH20-# (-# ~ bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 25 C(CF3)2NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 646 30 Co...pounds of the general formula I.A (n = 0), in which UR' i ethoxy, VR" i8 methylamino, ya iS -CH20-~ = bond to Aa) and Aa ' ~ i8 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 647 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-~ (-# = bond to Aa) and 40 Aa is 2,5-dichlorophenyl which carries a radical C(CF3)-NORiii in the 4 position, Riii for a co...~ound corresponding to one of the groups stated in Table C
~U~4~u4 Table 648 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa 5 is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 649 Co...~ ds of the general formula I.A (n = 0), in which UR' is methoxy, VR" is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a compound corresponding to one of the y~O~S
15 stated in Table C
~,..
Table 650 Col.lpoul,ds of the general formula I.A (n s 0), in which UR' is 20 ethoxy, VRn is methylamino, ya is -cH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CF3)=NORiii in the 3 position, Riii for a cuL,.puu~d corresponding to one of the groups stated in Table C
25 Table 651 Compounds of the general formula I.A (n = 0), in which UR' is methoxy, vR~ is methylamino, ya is -CH2O-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)3NORiii in the 30 5 position, Riii for a cv...~oulld corresponding to one of the groups ~- stated in Table C
. , Table 652 35 Compounds of the general formula I.A (n = 0), in which UR' is ethoxy, VR" is methylamino, ya is -CH20-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the S
position, Rlii for a compound corresponding to onè of the groups stated in Table c 179 21 ~9 122 Table C
5 No. Riii No. Riii 1 H 30 2-Cl-C6H4-CH2 2 CH3 31 3-Cl-C6H4-CH2 3 CH3CH2 32 4-Cl-C6H4-CH2 4 CH3CH2CH2 33 2,5-Cl2-C6H3-CH2 10 5 CH3CH(CH3) 34 2-CH3-C6H4-CH2 6 ~CH3)3C 35 3-CH3-C6H4-CH2 7 CH2=CH-CH2 36 4-CH3-C6H4-CH2 8 HC_C-CH2 37 2,3-(CH3)2-C6H3-CH2 15 9 CH30CH2CH2 38 2,4-(CH3)2-C6H3-CH2 ( 10 Cyclo~lO~yl-cH2 39 2,4,6-(CH3)3-C6H2-CH2 11 CH2=CH-CH2-CH2 40 2,4,6-(CH3)3-C6H2-CH2 12 CH3-cH=cH-cH2 41 2-CF3-C6H4-CH2 20 13 CH3-(CH2)3 42 3-CF3-C6H4-CH2 14 CH3-(CH2) 4 43 4-CF3-C6H4_CH2 CH3-(CH2)5 44 2-cF3-5-cH3-c6Hs-cH2 16 Cyclohexyl 45 2-CH3-5-CF3-C6H3-CH2 2-CH3-Cyclohexyl 46 2-Br-C6H4-CH2 18 CH3-CH2-C(CH3)2 47 2-(iso-Propyl)-C6H4-CH2 19 CH3-cH(cH3)-cH2 48 2-(iso-Propyl)-3-Cl-C6H3-CH2 CH3-CH(CH3)-CH2-CH2 49 2-CH3-5-~-C4-Hs-C6H3-CH2 21 CH2=c(cH3)-cH2 50 2-CH3-5-t-C4Hg-C6H3-CH2 30 22 HC-C-C~CH3)=CH-cH2 51 3-CH3-5-t-C4Hs-C6H3~cH2 23 Cl(CH3)-C=CH 52 2-Cl-5-t-C4Hg-C6H3-CH2 24 CH2=c(cl)-cH2- 53 3-cl-5-t-c4H9-c6H3-cH2 ClCH=CH-CH2- 54 2-OCH3-C6H4-CH2 35 26 C6Hs-CH2 3-OCH3-C6H4-CH2 28 3-F-C6H4-CH2 57 3-cH3-5-ocH3-c6H3-cH2 29 4-F-C6H4-CH2 58 3-Cl-5-0CH3-C6H3-CH2 Table 653 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 45 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 UV~4~4 position of the oxad-iazolyl ring and Xn corresponding for each co..,~ound to a line of Table D
Table 654 Compounds of the general formula I.A in which UR' i5 ethoxy, VR"
is methoxy, ya iS -CH2S-# (-$ e bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the cnmh;nAtion of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each 10 c~ ound to a line of Table D
Table 655 Compounds of the general formula I.A in which UR' i8 methylamino, 15 VRn i8 methoxy, ya i8 -CH2S-# (~~ - bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the co~hinAtion of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each co...pGund to a line of Table D
20 Table 656 CG...pounds of the general formula I.A in which UR' is ethylamino, VR" i8 methoxy, ya is -CH2S-# t-# = bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 25 position of the oxadiazolyl ring and Xn corresponding for each ~r..~oulld to a line of Table D
Table 657 30 Co,..~unds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-# (-~ = bond to Aa) and A~ is - 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 658 Compounds of the general form11l A I.A in which UR' is ethoxy, VRn is methylamino, ya is -CH2S-# (-~ = bond to Aa) and A~ is 40 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for each c~..*ound to a line of Table D
2199~22 Table 659 Compounds of the general formula I.A in which UR' i8 methoxy, VR~
i8 methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each ~o,.,~u..d to a line of Table D
Table 660 Compounds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each 15 compound to a line of Table D
f Table 661 Compounds of the general formula I.A in which UR' i8 methylamino, 20 VR" is methoxy, Y~ is -CH2S-# (-# = bond to Aa) and Aa i8 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn correspon~;ng for each c~m~ound to a line of Table D
25 Table 662 Compounds of the general formula I.A in which UR' is ethyl ~ml n VRn is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 30 position of the thiazolyl ring and Xn corresponding for each f compound to a line of Table D
, , , Table 663 35 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-~ (-# = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each coh,~und to a line of Table D
gO
Table 664 Col"~ou~lds of the general formula I.A in which UR' is ethoxy, VR~
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and A~ is 45 thiazol-2-yl, the combination of the substituent in the 4 UUS~45~U4 ~ 182 2199~22 position of the thiazolyl ring and Xn corresponding for each c~...~ou~,d to a line of Table D
Table 665 Compounds of the general formula I.A in which UR' is methoxy, VRn iB methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substi~uent in the 4 position of the thiazolyl ring and Xn corresponding for each 10 ~ ~o~l~d to a line of Table D
Table 666 Co,l-~ou~ds of the general formula I.A in which UR' i8 ethoxy, VR
15 is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each o~ ound to a line of Table D
ZO Table 667 Col..~o~nds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and Aa is thiazol-~-yl, the combination of the substituent in the 4 25 position of the thiazolyl ring and Xn corresponding for each cv...~ound to a line of Table D
Table 668 30 Co~.~ounds of the general formula I.A in which UR' is ethylamino, f VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa i8 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 669 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# (-~ = bond to Aa) and Aa i8 40 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each co~ ound to a line of Table D
2199~22 Table 670 Compounds of the general formula I.A in which UR' i8 ethoxy, VR~
i5 methylamino, ya is -CH20-~ (-# s bond to Aa) and Aa is 5 thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corxesponding for each compound to a line of Table D
Table 671 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa i3 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each 15 co...~o~-d to a line of Table D
( Table 672 Co...po~nds of the general formula I.A in which UR' is ethoxy, VR~
20 is methoxy, Y~ is -cH2o-# (-~ = bond to A~) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 673 Co...~oullds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 30 position of the thiazolyl ring and Xn corresponding for each f~ compound to a line of Table D
Table 674 35 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each co~ ound to a line of Table D
Table 675 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methylamino, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 45 5-methylthiazol-4-yl, the combination of the substituent in the 2 = :
~U~ / 4~
position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 676 Col.Lpounds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya i8 -CH20-# (-# - bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 677 Compounds of the general formula I.A in which UR' is methoxy, VR~
15 is methoxy, ya iS -cH2s-# (-~ = bond to Aa) and Aa is oxazol-2-yl, ¢~ the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each co..,~und to a line of Table D
20 Table 678 Co...pou"ds of the general form~ I.A in which UR' is ethoxy, VR~
is methoxy, ya iS -CH2S-# (-~ = bond to A~) and Aa i8 oxazol-2-yl, the cn~h~n~tion of the substituent in the 4 position of the 25 oxazolyl ring and Xn corresponding for each oo..~ound to a line of Table D
Table 679 30 C~".~o~l,ds of the general formula I.A in which UR' is methyl~no, ~- VR" is methoxy, Y~ is -CH2S-~ ~ bond to Aa) and A~ is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 680 CG.,~ou.-ds of the general formula I.A in which URr is ethylamino, VR" is methoxy, ya is -CH2S-~ = bond to Aa) and Aa is 40 oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each ~o.l,~ou..d to a line of Table D
Table 681 Compounds of the general formula I.A in which UR' is methoxy, VR
is methylamino, ya is -CH2S-# (-# = bond to Aa) and Aa i~
5 oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 682 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH2S-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a 15 line of Table D
~, Table 683 Compounds of the general formula I.A in which UR' is methoxy, VR"
20 is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 684 Compounds o~ the general formula I.A in which UR' is ethoxy, VRD
is methoxy, ya is -CHzO-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the 30 oxazolyl ring and Xn corresponding for each c~...pound to a line of Table D
. .
Table 685 35 Compounds of the general formula I.A in which UR' i8 methylamino, VRn iS methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 686 Compounds of the general formula ~.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 45 oxazol-2-yl, the comh; n~tion of the substituent in the 4 position .
186 2199~22 of the oxazolyl ring and Xn corresponding for each ~~...pound to a line of Table D
Table 687 Co~ oul~ds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# (-~ ~ bond to Aa) and Aa is oxazol-2-yl, the comh;~Ation of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each c~ ound to a 10 line of Table D
Table 688 Compounds of the general formula I.A in which UR' i8 ethoxy, VR
15 is methylamino, ya is -CH~0-# (-# = bond to Aa) and Aa is f oxazol-2-yl, the combination of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 689 Compounds of the general ~ormula I.A in which UR' is methoxy, VR"
is methoxy, ya iS -CH2S-# (-~ = bond to A~) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 25 position of the oxadiazolyl ring and Xn corresponding for each ~ IGuud to a line of Table D
Table 690 30 Compounds of the general formula I.A in which UR' iB ethoxy, VR"
- is methoxy, Y~ is -CH2S-# (-~ = bond to Aa) and Aa iB
1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 691 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 40 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
~ 2199~22 Table 692 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 693 Co"~ou"ds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya iS -CH2S-# (-# - bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each 15 ~o.,.pound to a line of Table D
f Table 694 Compounds of the general formula I.A in which UR' i8 ethoxy, VRn 20 is methylamino, ya is -cH2s-# (-~ = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oyA~ ~zolyl ring and Xn corresponding for each co..,pound to a line of Table D
25 Table 695 C~...pounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya i8 -CH20-# (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 30 position of the oxadiazolyl ring and Xn corresponding for each -- cG,,,~ou.. d to a line of Table D
Table 696 35 Compounds of the general formula I.A in which UR' i8 ethoxy, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 697 C~ ounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 45 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 ~J U :~ U ~
~ 2199~122 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 698 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the co~h;n~tion of the substituent in the 3 position o~ the oxadiazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 699 Compounds of the general formula I.A in which UR' is methoxy, VR"
15 is methylamino, ya is -CH20-~ (-# = bond to Aa) and Aa is f 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 700 C~...~o~nds of the general formul~ I.A in which UR' is ethoxy, VRn is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the combination of the substituent in the 3 25 position of the oxadiazolyl ring and Xn corresponding for each co..,~ound to a line of Table D
Table 701 30 Compounds of the general formula I.A in which UR' is methoxy, VR~
~-- is methoxy, ya is -CH2S-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 702 Co...~Gunds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is - CH2S~ 5 bond to Aa) and Aa is 40 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
2199!122 Table 703 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is 5 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each c~ oulld to a line of Table D
Table 704 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH2S-# (-# z bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each 15 cG...~oul,d to a line of Table D
f Table 705 Compounds of the general formula I.A in which UR' is methoxy, VR~
20 i5 methylamino, ya iS -cH2s-# (-# = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 706 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya i8 -CH2S-$ (-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 30 3 position of the thiadiazolyl ring and Xn corresponding for each ~ compound to a line of Table D
, . , Table 707 35 Compounds of the general formula I.A in which UR' i8 methoxy, VR~
is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 708 Compounds of the general formula I.A in which UR' i5 ethoxy, VR"
is methoxy, ya is -CH20-~ (-# 3 bond to Aa) and Aa is 45 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 0050~45204 -2199~22 3 position of the thiadiazolyl ring and Xn corresponding for each ~vm~ound to a line of Table D
Table 709 S
CG...pou~lds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya i5 -CH20-# (-# = bond to A~) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each 10 c~l..pound to a line of Table D
Table 710 Cu~ ul~ds of the general formula I.A in which UR' is ethylamino, 15 VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compo~l.d to a line of Table D
20 Table 711 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH20-# (-# e bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 25 3 position of the thiadiazolyl ring and Xn corresponding for each co".~oul,d to a line of Table D
Table 712 30 C~ oullds of the general formula I.A in which UR' i8 ethoxy, VRn f- is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is " 1,2,4-thiadiazol-5-yl, the combination of the substituent in the 3 position of the th; ~i azolyl ring and Xn corresponding for each cG.,.~oul~d to a line of Table D
Table 713 Co~ ou~lds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -cH2s-# (-# 2 bond to Aa) and Aa is 40 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each ~o..,~o~.ld to a line of Table D
2199!122 Table 714 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is metho~y, ya iS -CH2S-# (-# ~ bond to Aa) and Aa is 5 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 715 C~ o~..ds of the general formula I.A in which UR' is methylamino, VR" i8 methoxy, ya is -cH2s-# (-~ 5 bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 15 c~"l~ou~.d to a line of Table D
!' Table 716 Cv."~o~l-ds of the general formula I.A in which UR' is ethylamino, 20 VRn is methoxy, ya is -CH2S-# (-~ = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding ~or each compound to a line of Table D
25 Table 717 Compounds of the general formula I.A in which UR' i9 methoxy, VR
is methylamino, ya is -cH2s-# t-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the S
30 position of the isoxazolyl ring and Xn corresponding for each ,~ col-~ound to a line of Table D
Table 718 35 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH2S-# (-~ = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each cG.I*ound to a line of Table D
Table 719 Compounds of the general formula I.A in which UR' is methoxy, VR
is methoxy, ya iS -CH20-~ 5 bond to Aa) and Aa is 45 isoxazol-3-yl, the combination of the substituent in the 5 2199~22 position of the isoxazolyl ring and Xn co~Lesponding for each compound to a line of Table D
Table 720 Co~~unds of the general formula I.A in which UR' is ethoxy, VRn is methoxy, ya is -CH20-# (-# 2 bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 10 c~ ound to a line o~ Table D
Table 721 Compounds of the general formula I.A in which UR' is methylamino, 15 VRn is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 722 Compounds of the general formula I.A in which UR' i8 ethylamino, VRn i8 methoxy, ya iS -CH20-~ = bond to Aa) and Aa is isoxazol-3-yl, the cnmh~ n~tion of the substituent in the 5 25 position of the isoxazolyl ring and Xn corresponding for each c~ ~ul~d to a line of Table D
Table 723 30 Compounds of the general formula I.A in which UR' is methoxy, VRn ~- is methylamino, ya i8 -CH20-~' (-# = bond to Aa) and Aa is isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 724 Co."~u.,ds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-$ (-~ = bond to Aa) and Aa is 40 isoxazol-3-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each c~r..~o~,ld to a line of Table D
ooso/45204 2 1 9 9 ~ 2 2 Table 725 Compounds of the general formula I.A in which UR' i5 methoxy, VR"
is methoxy, ya iS -CH2S-~ (-# = bond to Aa) and Aa is 5 isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each cv.,~ound to a line of Table D
Table 726 Cv.~.~o~nds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH2S-# (-# = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each 15 compound to a line of Table D
r Table 727 C Junds of the general formula I.A in which UR' is methylamino, 20 VR" is methoxy, ya iS -CH2S-# (-# - bond to Aa) and A~ is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each cu~ und to a line of Table D
25 Table 728 Co,..~ullds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya iS -CH2S-# (-~ = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 30 position of the isothiazolyl ring and Xn corresponding for each f co.. yound to a line of Table D
Table 729 35 Co~ u,-ds of the general formula I.A in which UR' iY methoxy, VRn is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa iY
isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn correspo~ g for each cv,ll~ound to a line of Table D
Table 730 Compounds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa is 45 isothiazol-3-yl, the combination of the substituent in the S
2199~22 position of the isothiazolyl ring and Xn corresponding for each c~ ound to a line of Table D
Table 731 Compounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya is -CH20-# (-# - bond to AA) and Aa is isothiazol-3-yl, the c~ h;nation of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each 10 ~o..~o~lld to a line of Table D
Table 732 Compounds of the general formula I.A in which UR' is ethoxy, VR"
15 i8 methoxy, ya is -CH20-# ( -# 2 bond to Aa) and A~ is isothiazol-3-yl, the combination of the ~ubstituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 733 C~..,~ounds of the general formula I.A in which UR' is methylamino, VRn is methoxy, ya is -CH20-# (-# = bond to A~) and Aa is isothiazol-3-yl, the comh; nation of the substituent in the S
25 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 734 30 Compounds of the general formula I.A in which UR' is ethylamino, VR~' is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each c ~nd to a line of Table D
Table 735 Compounds of the general formula I.A in which UR' is methoxy, VR~
is methylamino, ya is -CH2O-# (-# = bond to Aa) and A~ is 40 isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
2199~22 Table 736 Compounds of the general formula I.A in which UR' i8 ethoxy, VR"
is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is S isothiazol-3-yl, the combination of the substituent in the 5 position of the isothiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 737 Compounds of the general formula I.A in which UR' is methoxy, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and A~ is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 15 ~...poul.d to a line of Table D
Table 738 Co,..~o~l.ds of the general ~ormula I.A in which UR' is ethoxy, VRn 20 is methoxy, ya iS -CH2O-# (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each ~v...pou~ld to a line of Table D
25 Table 739 Compounds of the general formula I.A in which UR~ is methyl~ ;no~
VR~' is methoxy, Y~ is -CH2O-~ (-# 2 bond to Aa) and An is pyrazol-3-yl, the combination of the substituent in the 1 30 position of the pyrazolyl ring and Xn corresponding for each ~' compound to a line of Table D
Table 740 35 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent~in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 741 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya is -CH20-# ( ~# 3 bond to Aa) and Aa is 45 pyrazol-3-yl, the combination of the substituent in the 1 ~ 2199422 position of the pyra201yl ring and Xn corresponding for each compound to a line of Table D
Table 742 Compounds of the general formula I.A in which UR' is ethoxy, VRn is methylamino, ya iS -CH20-# (-# = bond to Aa) and Aa is pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 743 compounds of the general formula I.A in which UR' is methoxy, VRn 15 is methoxy, ya iS -CH2S~ # = bond to A~) and Aa i8 ( pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each c~i..pound to a line of Table D
20 Table 744 Compounds of the general formula I.A in which UR' is ethoxy, VR~
i8 methoxy, ya i8 -CH2S-# (-# = bond to Aa) and A~ is pyrazol-4-yl, the c~mh;n~tion of the substituent in the 1 25 position of the pyrazolyl ring and Xn corresponding for each cv...po~nd to a line of Table D
Table 745 30 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-# (-~ 5 bond to A~) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding ~or each compound to a line of Table D
Table 746 Co,..~ou,.ds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH25-# (-# = bond to A~) and Aa is 40 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
~199122 Table 747 .
Compounds of the general formula I.A in which UR' is methoxy, VR"
is methylamino, ya is -CH2S-# (-# = bond to Aa) and Aa iS
5 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each co..,yvund to a line of Table D
Table 748 Compounds of the general formula I.A in which UR' i8 ethoxy, VR"
is methylamino, ya iS -CH2S-# (-# = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 15 c~.l,Qo~nd to a line of Table D
Table 749 Compounds of the general formula I.A in which UR' is methoxy, VR"
20 is methoxy, ya is -CH2o-$ (-# = bond to Aa) and Aa i8 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each cvmpvund to a line of Table D
25 Table 750 Co..,pounds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 30 position of the pyrazolyl ring and Xn corresponding for each ~- o~.,lpoulld to a l~ne of Table D
Table 751 35 Compounds of the general formula I.A in whi~h UR' is methylamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each ~vmyound to a line of Table D
Table 752 Compounds of the general formula I.A in which UR' is ethylamino, VR i5 methoxy, ya iS -CH20-# (-~ s bond to A~) and Aa is 45 pyrazol-4-yl, the combination of the substituent in the 1 ~ /4~U4 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 753 C~ o~.lds of the general form~ I.A in which UR' is methoxy, VRn is methylamino, ya i5 -CH20-# (-~ = bond to A~) and Aa i5 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 754 Cv,ll~G~nds of the general formula I.A in which UR' i8 ethoxy, VR~
15 is methylamino, Y~ is -CH20-# ~-# s bond to A~) and Aa is f pyrazol-4-yl, the combination of the substituent in the 1 ' position of the pyrazolyl ring and Xn corresponding for each cGm~ound to a line of Table D
20 Table 755 Cu.-,~oullds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya is -CH2S-~ = bond to Aa) and A~ i8 1,2,4-triazol-3-yl, the combination of the substituent in the 1 25 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 756 30 Compounds of the general formula I.A in which UR' is ethoxy, VR~
is methoxy, ya is -CH2S-# (-# = bond to A~) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 757 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH2S-~ (-# z bond to A~) and A~ is 40 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corre~ponding for each co,,.p~nd to a line of Table D
~u~U/~ 4 219~ 1 22 Table 758 C: l~unds of the general formula I.A in which UR' i5 ethylamino, VR" i8 methoxy, ya is -CH2S-~' (-# = bond to Aa) and Aa is 5 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each cG.,~o~d to a line of Table D
Table 759 Compounds of the general formula I.A in which UR' is methoxy, VRn is methylamino, ya iS -CH2S-~ = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each 15 compound to a line of Table D
'' ' ~
Table 760 Compounds of the general formula I.A in which UR' is ethoxy, VR"
20 is methylamino, ya iS -CH2S-~ bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
25 Table 761 Compounds of the general formula I.A in which UR' is methoxy, VR"
is methoxy, ya iS - CH20-# (-~ 3 bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 30 position of the 1,2,4-triazolyl ring and Xn corresponding for each cv...~ound to a line of Table D
Table 762 35 Co~pounds of the general formula I.A in which UR' is ethoxy, VR"
is methoxy, ya iS -CH20-~' (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazolyl ring and Xn corresponding for each .~...~ound to a line of Table D
Table 763 Compounds of the general formula I.A in which UR' is methylamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 45 1,2,4-triazol-3-yl, the combinati~n of the substituent in the 1 ~19g~22 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table 764 Compounds of the general formula I.A in which UR' is ethylamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa i8 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2~4-triazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 765 Compounds of the general formula I.A in which UR' is methoxy, VR"
lS is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the cnmh~n~tion of the substituent in the position of the 1,2,4-triazolyl ring and Xn corresponding for each cv.*oulld to a line of Table D
20 Table 766 Co...~o~..ds of the general formula I.A in which UR' is ethoxy, VR"
is methylamino, ya is -CH20-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 25 position of the 1,2,4-triazolyl ring and Xn corresponding for each compound to a line of Table D
Table D
30 No. n R~
.~ 1 H C6H5 2 3-Cl C6H5 3 4-Cl C6H5 4 6-Cl C6H5 4-F C6Hs 6 4-OCH3 C6Hs 7 3-CH3 C6Hs 8 6-CH3 C6Hs H '3-F-C6H~
11 H 4-F-C6H~
12 H 2,3-F2-C6H3 45 13 H 2,4--F2-C6H3 14 H 2,5-F2-C6H3 lS H 2,6-F2-C6H3 ~Ju~ ~u~
2199~22 No. n R~
16 H 3,4-F2-C6H3 17 H 3,5-F2-C6H3 18 H 2-Cl-C6H4 19 H 3-Cl-C6H4 H 4-Cl-C6H4 21 3-C1 4-Cl-C6H4 22 4-C1 4-Cl-CcH4 23 6-C1 4-Cl-CcH4 24 4-F 4-Cl-CCH4 4-OCH3 4-Cl-c6H4 26 3-CH3 4-Cl-CcH4 27 6-CH3 4-Cl-CcH~
f 28 H 2,3-Cl2-C6H3 29 H 2,4-Cl2-C6H3 H 2,5-Cl2-C6H3 31 H 2,6-Cl2-C6H3 32 H 3,4-C12-C6H3 33 H 3,5-Cl2-C6H3 34 H 2,3,4-C13-C6H2 H 2,3,5-C13-C6H2 36 H 2,3,6-c13-c6H2 37 H 2,4,5-C13-C6H2 38 H 2,4,6-C13-C6H2 39 H 3,4,5-C13-C6H2 30 40 H 2-Br-C6H4 r 41 H 3-Br-CcH4 42 H 4-Br-C6H4 43 H 2,4-Br2-CcH3 44 H 2-Br, 4-F-C6H3 H 2-Br, 4-Cl-C6H3 46 H 2-F, 4-Cl-C6H
47 H 3-F, 4-Cl-C6H3 48 H 3-Cl, 5-F-C6H3 49 H 2-Cl, 4-F-C6H3 52 H 4-CN-C6H~
53 H 3-CN, 4-Cl-C6H3 0U50/452~4 219~ 122 No. n R~
H 4-H2N-C( 5S ) -C6H~
59 H 2,4-(CH3)2-C6H3 H 2,5-(CH3)2-C6H3 61 H 2,5-(CH3)2-C6H3 62 H 2,6-(CH3)2-C6H3 63 H 3,4-(CH3)2-C6H3 64 H 3,5-(CH3)2-C6H3 H 2,4,6-(CH3)3-C6H2 15 66 H 3,4,5-(CH3)3-C6H2 ( 67 H 2-CH3, 4-Cl-C6H3 68 H 2-Cl, 4-CH3-C6H3 69 H 3-CH3, 4-Cl-C6H3 20 70 H 3-Cl, 5-CH3-C6H3 71 H 2-CN, 4-CH3-C6H3 72 H 2-CH3., 4-CN-C6H3 73 H 4-(C2Hs)~C6H4 ~ 25 H 4-tC(CH3)3]-C6H~
H 3-(C6Hs)-C6H4 76 H 4-(C6H5)-C6H~
77 H 2-CF3-C6H~
30 79 H 4-CF3-C6H~
r 80 H 3,5-(CF3)2-C6H3 81 H 2-Cl, 4-CF3-C6H3 82 H 2-OCH3-C6H~
35 83 H 3-OCH3-C6H~
84 H 4-OCH3-C6H~
H 2,4-(OCH3)2-C6H3 86 H 3,4-(OCH3)2-C6H3 40 87 H 2,5-(OCH3)2-C6H3 88 H 3,5-(OCH3)2-C6H3 89 H 3,4,5-(OCH3)3-C6H2 H 2-CH3, 4-OCH3-C6H3 91 H 2-Cl, 4-OCH3-C6H3 92 H 4-OCF3-C6H~
93 H 2-0CHF2-C6H~
~U~/4~u4 203 2~ 99~122 No. n R~
H 4-ocHF2-c6H4 5 96 H 4-(OCF2CHF2)-C6H~
97 H 2-F, 4-OCHF2-C6H3 98 H 4-(OCH2CH3)-C6H4 99 H 4-tOC(CH3)3]-C6H~
100 H 3-(CO2CH3)-C6H~
101 H 4-(CO2CH3)-C6H~
102 H 4-[CO2C~CH3) 3 ] -C6H4 103 H 2,3-~O-CH2-0]-C6H3 104 H 3,4-[O-CH2-O]-C6H3 15 105 H 3~4-to-c(cH3)2-o]-c6H3 ( 106 H 3,4-[O-CH2CH2-O~-C6H3 107 H 2,3-[(CH2)~]-C6H3 108 H 3,4-[(CH2)4]-CcH3 20 109 H 2,3-(CH=CH2-CH=CH)-C6H3 110 H 3,4-(CH=CH-CH=CH)-C6H3 114 H C(CH3)2 116 H CHCH(CH3)2 117 H CH(CH3)CH2CH3 3 llô H C(CH3)3 (~ 119 H Cyclopropyl 120 H Cyclohexyl 121 H 2-Tetrahydrofuranyl 35 122 H 3-Tetrahydrofuranyl 123 H 3-Tetrahydrothienyl 124 H 2-1,3-Dioxolenyl 125 H 2-1,3-Dioxanyl 40 126 H 4-Tetrahydropyranyl 127 H Pyrid-2-yl 128 H 5-Cl-Pyrid-2-yl 129 H 5-CF3-Pyrid-2-yl 219~122 Table 767 Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VR" is methoxy, ya is -CH=CH- and Aa is a heterocyclic 5 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 768 10 C _~oundg of the general formula I.A (n = 0) in which UR' is ethoxy, VR" is methoxy, ya is -CH=CH- and Aa i8 a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.l 15 Table 769 ~' Compounds of the general formula I.A (n - 0) in which UR' is methoxy, VR" is ethoxy, ya is -CH=CH- and A~ is a heterocyclic structure, this heterocyclic structure corresponding for each 20 compound to a line of Table D.l Table 770 Compounds of the general formula I.A (n = 0) in which UR' i8 25 ethoxy, VR" is ethoxy, ya is -CH=CH- and Aa i9 a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 771 f-- Compounds of the general formula I.A (n = 0) in which UR' is methylamino, VR" i5 methoxy, ya is -CH=CH- and Aa is a heterocyclic structure, thi~ heterocyclic structure corresponding for each c _-~und to a line of Table D.1 Table 772 Compounds o~ the general formula I.A (n = 0) in which UR' is ethylamino, VR" is methoxy, ya is -CH=CH- and Aa is a heterocyclic 40 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l 0050~45204 -Table 773 Compounds of the general formula I.A (n = 0) in which UR' is methylamino, VR" is ethoxy, ya is -CH=CH- and Aa is a heterocyclic 5 structure, this heterocyclic structure corresponding for each compound to a line of Table D.l Table 774 10 C~ oUnds of the general formula I.A (n = 0) in which UR' is ethylamino, VR" is ethoxy, ya iS -CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each co~ und to a line of Table D.l .
15 Table 775 f.
Compounds of the general formula I.A (n Q 0) in which UR' is methoxy, VR" is methylamino, ya is -CH=CH- and A~ is a heterocyclic structure, this heterocyclic structure corresponding 20 for each compound to a line of Table D.1 Table 776 C~ ~ounds of the general formula I.A (n - 0) in which UR' is 25 ethoxy, VRn is methylamino, ya is -CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each compound to a line of Table D.1 Table 777 ~-~ Compounds of the general formula I.A (n = 0) in which UR' is methoxy, VRn is ethylamino, ya is -CH-CH- and Aa is a heterocyclic structure, thi3 heterocyclic structurQ corresponding for each compound to a line of Table D.l Table 778 Compounds of the general formula I.A (n = 0) in which UR' is ethoxy, VR" is ethylamino, ya is -CH=CH- and Aa is a heterocyclic 40 structure, thi~ heterocyclic structure corresponding for each compound to a line of Table D.1 00~0/45204 ~ 2199~22 Table D.l No. Het 5 01 1--CE~3 py~ L~)l--3--yl 02 l-CH(CB3)2 py~ ~3~y 03 1 - C (CB3)3 py~Ol~3~y 04 1-cyclo~ yl-pyrrol-3 05 l-C6H~ ~y~L~1~3~yl 06 1-(2-CB3-C6B4)-pyrrol-3-yl 07 1-(3-CB3-C6H4)-pyrrol-3-yl 08 1-(4-CH3-C6H4)-pyrrol-3-yl o9 1-(3-OCH3-CGH4) PYLrO1-3-Y1 15 10 1-(4-OCH3-C6H~)-pyrrol-3-yl 11 1-(4-N02-C6H4)-pyrrol-3-yl 12 1-(3-N02-C6B~)-pyrrol-3-yl 13 1-(4-CN-C6~4)-pyrrol-3-yl 14 1-(3-CN-C6~4) PYLL~1_3_Y1 1-(3-CF3-C6H4)-pyrrol-3-yl 16 1-(4-CF3-C6H~)-pyrrol-3-yl 17 1-(4-C(CB3)3-C6H4)-pyrrol-3-yl 18 1-(4-CCHs-C6H4) pyL ~ ol-3-yl 25 19 1--(2--Cl--C6H4) pyL~ ol--3--yl 1-(3-Cl-C6H~) ~yL~Ol~3~y 21 1-(4-Cl-C6H4) py~Ol~3~yl 22 1-(2-Br-C6H4) prLLol-3-yl 23 1-(3-Br-C6H~) prL~ol-3-yl 24 l-(4-sr-c6H4)-pyrrol-3 1-(2-F-C6H~)-pyrrol-3-yl 26 1-(3-F-C6H~)-pyrrol-3-yl 27 1-(4-F-C6B~)-pyrrol-3-yl 35 28 1-(2,4-Cl2-C6H3)-pyrrol-3-yl 29 1-(2,5-Cl2-C6B3)-pyrrol-3-yl 1-(2,6-Cl2-C6H3)-pyrrol-3-yl 31 1-(3,4-Cl2-C6H3)-pyrrol-3-yl 32 1-(2,4-F2-C6~3)-pyrrol-3-yl 40 33 1-( 2,5-F2-C6B3)-pyrrol-3-yl 34 1-( 2,6-F2-C6H3)-pyrrol-3-yl 1-(3,4-F2-C6H3) py ol-3-yl 36 1--(2-Cl, 5--ocH3-c6B3)-pyrrol--3-yl 45 37 1-( 2 - Cl, 5-CB3-C6B3)-pyrrol-3-yl 38 1-(5-Cl, 2-OCH3-C6~3)-pyrrol-3-yl 39 1-(5-Cl, 2-CB3-C6H3)-pyrrol-3-yl 00~0/45204 ~1994~2 No. Het 1-t2,5-(CH3)2-C6H3]-pyrrol-3-yl 41 1-CH3-pyrrol-2-yl 42 1-CH(CH3)l-~y~ ~2-y 43 1-C(CH3)3-pyrrol-2-yl 44 1-cyclopropyl-pyrrol-2-yl 1-C6H~ ~yL~1~2~yl 46 1-~2-CH3-CtH4) ~yLL~1~2~yl lO 47 1-(3 CB3-C6H4) ~rLLol-2-yl 48 1-(4-CH3-C6H4) PYLL~1_2_Y1 49 1-(3-OCH3-C6H4) PYL~O1-2-Y1 1-(4-OCH3-C6H~) ~yL~vl~2~yl 15 51 1-(4-NO2-C6H~) ~ylLul~2~yl f 52 1-(3-N02-CcH4) ~yLL~1~2~yl 53 1-(4-CN-C6H~) p~L ol-2-yl 54 1-(3-CN-C6H~) ~y Lol-2-yl 1-(3-CF3-C6H~) PYLSU1-2-Y1 20 56 1-(4-CF3-C6H~) PY~L~1_2_Y
57 1-(4-C(CH3)3-C6H4) ~yLLol~2~y 58 1-(4-C6H5-C6H~) PYL~V1-2-Y1 59 1-(2-C1-C6H4) ~YLL~1_2_Y1 1-(3-Cl-C6H4) ~yLLOl-2-yl 1-(4-Cl-C6H~) ~yL~1-2-yl 62 1-(2-Br-C6H4) ~yLLOl~2~y 63 i--( 3--Br--C6H4 ) e~yL~ 2--yl 64 1-(4-Br-C6H~) ~yL~ol~2~y 30 65 1-(2-F-C6H4) PYLLO1-2-Y1 f 66 1-(3-F-C6H4) PYLL~1-2_Y1 67 1-(4-F-C6H4) PYLLO1-2-Y1 68 1-(2,4-C12-C6H3) ~YLLO1_2_Y1 69 1 - ( 2,5-Cl2-C6H3)-pyrrol-2-yl 1-(2,6-C12-C6H3) ~ylLol-2-yl 71 l-(3,4-Cl2-C6H3)-pyrrol-2-yl 72 l-(2,4-F2-C6H3)-pyrrol-2-yl 73 1-(2,5-F2-C6H3)-pyrrol-2-yl 40 74 1-(2,6-F2-C6H3)-pyrrol-2-yl l-(3,4-F2-C6H3)-pyrrol-2-yl 7 6 1 - ( 2-Cl, 5-OCH3-C6H3)-pyrrol-2-yl 77 1-(2-Cl, 5-CH3-C6H3)-pyrrol-2-yl 78 1-(5-Cl, 2-OCH3-C6R3)-pyrrol-2-yl 79 1-(5-Cl, 2-CH3-C6H3)-pyrrol-2-yl 1-[2,5-(CH3)2-C6H3]-pyrrol-2-yl 2~99;1~2 No. Het 81 5-CH3-furan-2-yl 82 5-CB(CH3)2-furan-2-yl 83 5-C(CH3)3-fulan 2-yl 84 5-cyclv~r~yl-furan-2 5-C6Hs-furan-2-yl 86 5-(2-CH3-C6H4)-furan-2-yl 87 5-(3-CH3-C6H4)-furan-2-yl 10 88 5-(4-CH3-C6H4)-furan-2-yl 89 5-(3-OCH3-C6H4)-furan-2-yl 5-(4-OCH3-C6H4)-furan-2-yl 91 5-(4-N02-4H4)-furan-2-yl 15 92 5-(3-N02-C6H~)-furan-2-yl f 9 3 5-(4-CN-C6H~)-furan-2-yl 94 5-(3-CN-C6H4)-fu~ d~- 2-yl 5-(3-CF3-C6H~)-furan-2-yl 96 5-(4-CF3-C6H4)-furan-2-yl 20 97 5-(4-C(CH3)3-C6H4)-furan-2-yl 98 5-(4-C6H5-C6H4)-furan-2-yl 99 5-(2-Cl-C6H~)-furan-2-yl.
100 5-(3-Cl-C6H~)-furan-2-yl 2 101 5-(4-Cl-C6H4)-furan-2-yl 102 5-(2-~3r-C6H~)-furan-2-yl 103 5-(3-ar-c6H~) fu~dr. 2-yl 104 5-(4-Br-C6H~)-furan-2-yl 105 5-(2-F-C6H~)-furan-2-yl 30 106 5-(3-F-C6H4)-furan-2-yl 107 5-(4-F-C6H~)-furan-2-yl 108 5-(2,4-Cl2-C6H3)-furan-2-yl 109 5-(2,5-Cl2-C6H3)-furan-2-yl 110 5--(2,6-C12-C6H3)-furan--2--yl 111 5-(3,4-Cl2-C6H3)-furan-2-yl 112 5-(2,4-F2-C6H3)-furan-2-yl 113 5-(2,5-F2-C6H3)-furan-2-yl 114 5-(2,6-F2-C6H3)-furan-2-yl 40 115 5-(3,4-Fz-C6H3)-furan-2-yl 116 5-(2-Cl, 5-OCH3-C6H3)-furan-2-yl 117 5-(2-Cl, 5-CH3-C6H3)-furan-2-yl 118 5-(5-Cl, 2-OCH3-C6H3)-furan-2-yl 119 5-(5-Cl, 2-CH3-C6H3)-furan-2-yl 120 5-[2,5-(CH3)z-C6H3]-furan-2-yl 121 4-CH3-furan-2-yl 0050~452~4 2~9!~22 No. Het 122 4-CH(CH3)2-furan-2-yl 123 4-C(CH3)3-furan-2-yl 124 4-cyclG~ yl-furan-2-yl 125 4-C6Hs-furan-2-yl 126 4-(2-CH3-C6H4)-furan-2-yl 127 4-(3-CH3-C6H4)-furan-2-yl 128 4-(4-CH3-C6~4)-furan-2-yl 10 129 4-(3-OCH3-C6H4)-furan-2-yl 130 4-(4-OCH3-C6H4)-fu~an 2-yl 131 4-(4-N02-C6H4)-furan-2-yl 132 4-(3-N02-C6H4)-furan-2-yl 15 133 4-(4-CN-C6H~)-furan-2-yl 134 4-(3-CN-C6H4)-furan-2-yl -~ 135 4-(3-CF3-C6~4)-furan-2-yl 136 4-(4-CF3-C6H~)-furan-2-yl 137 4-(4-C(CH3)3-4 H4)-furan-2-yl 2~ 138 4-(4-C6H5-C6H~)-furan-2-yl 139 4-(2-Cl-C6H4)-furan-2-yl 140 4-(3-Cl-4H4)-furan-2-yl 141 4-(4-Cl-C6H4)-furan-2-yl 142 4-(2-Br-C6H~)-furan-2-yl 143 4-(3-Br-C6H~)-furan-2-yl 144 4-(4-Br-C6H4)-furan-2-yl 145 4-(2-F-C6H4)-furan-2-yl 146 4-(3-F-C6H4)-fu~ar. 2-yl 30 141 4-(4-F-C6H4)-~~-an 2-yl 148 4-(2,4-Cl2-C6H3)-furan-2-yl 149 4-(2,5-Cl2-C6H3)-furan-2-yl 150 4-(2,6-Cl2-C6H3)-furan-2-yl lS1 4-(3,4-Cl2-C6H3)-furan-2-yl 152 4-(2,4-F2-C6H3)-furan-2-yl 153 4-(2,5-F2-C6H3)-furan-2-yl 154 4-(2,6-F2-C6H3)-furan-2-yl 155 4-(3,4-F2-4H3)-furan-2-yl 40 156 4-(2-Cl, 5-OCH3-C6H3)-furan-2-yl 157 4-(2-Cl, 5-CH3-C6H3)-furan-2-yl 158 4-(5-Cl, 2-OCH3-C6H3)-furan-2-yl 159 4-(5-Cl, 2-CH3-C6H3)-furan-2-yl 160 4-[2~5-(c~3)2-c6H3]-furan-2 45 161 5-CH3-thien-2-yl 162 5-CH(CH3)2-thien-2-yl 2193~122 No. Het 163 5-C(CH3)3-thien-2-yl 164 5-cycl~p~ l-thien-2-yl 165 5-CcH5-thien-2-yl 166 5-(2-CH3-C6H4)-thien-2-yl 167 5-(3-CH3-CcH~)-thien-2-yl 168 5-(4-CH3-CcH~)-thien-2-yl 169 5-(3-OCH3-4H4)-thien-2-yl 1?0 5-(4-OCH3-C6H4)-thien-2-yl 171 5-(4-N02-C6H~)-thien-2-yl 172 5-(3-N02-CcH4)-thien-2-yl 173 5-(4-CN-CcH4)-thien-2-yl 174 5-(3-CN-CcH~)-thien-2-yl 175 5-(3-CF3-C6H~)-thien-2-yl 176 5-(4-CF3-C6H4)-thien-2-yl 177 5-(4-C(CH3)3-C6H~)-thien-2-yl 178 5-(4-C6B5-C6H4)-thien-2-yl 20 179 5-(2-Cl-C6H~)-thien-2-yl 180 5-(3-Cl-CcH4)-thien-2-yl 181 5-(4-Cl-CcH4)-thien-2-yl 182 5-(2-Br-C6~)-thien-2-yl 183 5-(3-Br-CcH4)-thien-2-yl 184 5-(.4-~r-C6H~)-thien-2-yl 185 5-(2-F-C6H4)-thien-2-yl 186 5-(3-F-C6H4)-thien-2-yl 187 5-(4-F-C6H4)-thien-2-yl 30 188 5-(2,4-Cl2-C6H3)-thien-2-yl - 189 5-(2,5-Cl2-C6H3)-thien-2-yl 190 5--(2,6-C12--C6H3)-thien--2--yl 191 5-(3,4-Cl2-C6H3)-thien-2-yl 192 5-(2,4-F2-CcH3)-thien-2-yl 193 5-(2,5-F2-CcH3)-thien-2-yl 194 5-(2,6-F2-C6H3)-thien-2-yl 195 5-(3,4-F2-CcH3)-thien-2-yl 196 5-(2-Cl, 5-OCH3-C6H3)-thien-2-yl 197 5-(2-Cl, 5-CH3-C6H3)-thien-2-yl 198 5-(5-Cl, 2-OCH3-C6H3)-thien-2-yl 199 5-(5-Cl, 2-CH3-C6H3)-thien-2-yl 200 5-[2,5-(CH3)2-C6H3]-thien-2-yl 201 4-CH3-thien-2-yl 202 4-CH(CH3)2-thien-2-yl 203 4-C(CH3)3-thien-2-yl ~ 211 2199~22 No. Het 204 4-cyclopropyl-thien-2-yl 205 4-C6H5-thien-2-yl 206 4-(2-CH3-C6H4)-thien-2-yl 207 4-(3-CH3-C6~4)-thien-2-yl 208 4-(4-CH3-C6H~)-thien-2-yl 209 4-(3-OCH3-CcH4)-thien-2-yl 210 4-(4-OCH3-C6H~)-thien-2-yl lO 211 4-(4-NO2-C6H4)-thien-2-yl 212 4-(3-NO2-C6H4)-thien-2-yl 213 4-(4-CN-C6H4)-thien-2-yl 214 4-(3-CN-C6H~)-thien-2-yl 15 215 4-(3-CF3-C6Hg)-thien-2-yl f~ 216 4-(4-CF3-C6H~)-thien-2-yl 217 4-(4-C(CH3)3-C6H~)-thien-2-yl 218 4-(4-C6H5-C6H~)-thien-2-yl 219 4-(2-Cl-C6H4)-thien-2-yl 20 220 4-(3-Cl-C6H~)-thien-2-yl 221 4-(4-Cl-C6H4)-thien-2-yl 222 4-(2-Br-C6H4)-thien-2-yl 223 4-(3-Br-C6H~)-thien-2-yl 224 4-(4-Br-C6H~)-thien-2-yl 225 4-(2-F-C6H~)-thien-2-yl 226 4-(3-F-C6H~)-thien-2-yl 227 4-~4-F-C6H4)-thien-2-yl 228 4-(2,4-Cl2-C6H3)-thien-2-yl 30 229 4-(2,5-Cl2-C6H3)-thien-2-yl ~~ 230 4-(2,6-Cl2-C6H3)-thien-2-yl 231 4-(3,4-Clz-C6H3)-thien-2-yl 232 4-(2,4-F2-4H3)-thien-2-yl 233 4-(2,5-F2-C6H3)-thien-2-yl 234 4-(2,6-F2-CcH3)-thien-2-yl 235 4-(3,4-F2-CGH3)-thien-2-yl 236 4-(2-Cl, 5-OCH3-C6H3)-thien-2-yl 237 4-(2-Cl, 5-CH3-C6H3)-thien-2-yl 40 238 4-(5-Cl, 2-OCH3-C6H3)-thien-2-yl 239 4-(5-Cl, 2-CH3-C6H3)-thien-2-yl 240 4-~2,5-(CH3)2-C6H3]-thien-2-yl 241 2-CH3-thien-4-yl 242 2-CH(CH3)2-thien-4-yl 243 2-C(CH3)3-thien-4-yl 244 2-cyclopl~pyl-thien-4-yl No. Het 245 2-C6H5-thien-4-yl 246 2-(2-CH3-C6H4)-thien-4-yl 5 247 2-(3-CH3-4 H~)-thien-4-yl 248 2-(4-CH3-C6H~)-thien-4-yl 249 2-(3-OC~3-C6H~)-thien-4-yl 250 2-(4-OCH3-C6H~)-thien-4-yl 251 2-(4-NO2-C6H4)-thien-4-yl 10 252 2-(3-NO2-C6H4)-thien-4-yl 253 2-(4-CN-C6H~)-thien-4-yl 254 2-(3-CN-C6H~)-thien-4-yl 255 2-(3-CF3-C6H4)-thien-4-yl 5 256 2-(4-CF3-C6H4)-thien-4-yl 1 257 2-(4-C(C83)3-C6H~)-thien-4-yl 258 2-(4-CGHs-Cc~)-thien-4-yl 259 2-(2-Cl-C6H~)-thien-4-yl 260 2-(3-Cl-C6H~-thien-4-yl 261 2-(4-Cl-C6H~)-thien-4-yl 262 2-(2-Br-C6H4)-thien-4-yl 263 2-(3-Br-C6H~)-thien-4-yl 264 2-(4-Br-C6H4)-thien-4-yl 265 2-(2-F-C6H~)-thien-4-yl 266 2-(3-F-C6H4)-thien-4-yl 267 2-(4-F-C6H~)-thien-4-yl 268 2-(2,4-Cl2-C6H3)-thien-4-yl 269 2-(2,5-Cl2-C6H3)-thien-4-yl 30 270 2-(2,6-Cl2-C6H3)-thien-4-yl ~- 271 2-(3,4-Cl2-C6H3)-thien-4-yl 272 2-(2,4-F2-C6H3)-thien-4-yl 273 2-(2,5-F2-C6H3)-thien-4-yl 274 2-(2,6-F2-C6H3)-thien-4-yl 275 2-(3,4-F2-C6H3)-thien-4-yl 276 2-~2-Cl, 5-OCH3-C6H3)-thien-4-yl 277 2-(2-Cl, 5-CH3-C6H3)-thien-4-yl 278 2-(5-Cl, 2-OCH3-C6H3)-thien-4-yl 40 279 2-(5-Cl, 2-CH3-C6H3)-thien-4-yl 280 2-t2,5-(CH3)2-C6H3]-thicn-4-yl 281 l-CH3-pyrazol-4-yl 282 l-CH(CH3)2-pyrazol-4-yl Z83 l-C(CH 3 )3-pyrazo1-4-yl 284 1-cyclopropyl-pyrazol-4-yl 285 l-C6H5-pyrazol-4-yl O~SU~ 4~ J4 ~ 213 2~99122 No. Het 286 1-(2-CH3-C6H4)-pyrazol-4-yl 287 1-(3-CB3-C6H4)-pyrazol-4-yl 5 288 1-(4-CH3-C6H4)-pyrazol-4-yl 289 1-(3-OCH3-C6H4)-pyrazol-4-yl 290 1-(4-OCR3-C6H~)-pyrazol-4-yl 291 1-(4-NO2-C6H~)-pyrazol-4-yl 292 1-(3-NO2-C6H~)-pyrazol-4-yl 10 293 1-(4-CN-C6H4)-pyrazol-4-yl 294 1-(3-CN-C6H4)-pyrazol-4-yl 295 1-(3-CF3-C6H4)-pyrazol-4-yl 296 1-(4-CF3-C6Hg)-pyrazol-4-yl 15 297 1-(4-c(cH3)3-c6H~)-pyrazol-4 298 1-(4-C6H5-CcH~)-pyrazol-4-yl 299 1-(2-Cl-C6H4)-pyrazol-4-yl 300 1-(3-Cl-C6H~)-pyrazol-4-y 301 1-(4-Cl-C6H4)-pyrazol-4-yl 20 302 1-(2-Br-C6H~)-pyrazol-4-yl 303 1-(3-Br-4H~)-pyrazol-4-yl 304 l-(4-Br-C6H4)-pyrazol-4-yl 305 1-(2-F-C6H4)-pyrazol-4-yl 306 1-(3-F-C6H~)-pyrazol-4-yl 307 1-(4-F-C6H~)-pyrazol-4-yl 308 1-(2,4-C12-C6H3)-pyrazol-4-yl 309 1-(2,5-C12-C6H3)-pyrazol-4-yl 230 1-(2,6-C12-C6R3)-pyrazol-4-yl 30 311 1-(3,4-C12-C6H3)-pyrazol-4-yl f 312 l-(2,4-F2-C6~3)-pyrazol-4-yl 313 l-(2,5-F2-C6H3)-pyrazol-4-yl 314 1-(2,6-F2-C6H3)-pyrazol-4-yl 315 l-(3,4-F2-CcH3)-pyrazol-4-yl 316 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 311 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 318 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 319 1-(5-Cl, 2-CH3-C6H3)-pyrazol-4-yl 40 320 l-t2~5-(cH3)2-c6H3]-pyrazol-4 321 1,5-(CH3)2-pyrazol-3-yl 322 1-CH3, 5-CH(CH3)2-pyrazol-3-yl 323 1-CH3, 5-C(CH3)3-pyrazol-3-yl 324 1-CH3, 5-cyclopLv~yl-pyrazol-3 325 l-CH3, 5-C6H5-pyrazol-3-yl 326 1-CH3, 5-(2-CH3-C6H4)-pyrazol-3-yl ~ 214 2199122 No. Het 327 1-CH3, 5-(3-CB3-C6H4)-pyrazol-3-yl 328 1-CH3, 5-(4-CH3-C6H4)-pyrazol-3-yl 5 329 1-CH3, 5-(3-OCH3-C6H4)-pyrazol-3-yl 330 1-CH3, 5-(4-OCH3-C6H4)-pyrazol-3-yl 331 1-CH3, 5-(4-N02-C6H4)-pyrazol-3-yl 332 1-CH3, 5-(3-N02-C6H4)-pyrazol-3-yl 333 1-CH3, 5-(4-CN-C6H4)-pyrazol-3-yl 0 334 1-CH3, 5-(3-CN-C6H~)-pyrazol-3-yl 335 1-CH3, 5-(3-CF3-C6H4)-pyrazol-3-yl 336 l-CH3, 5-(4-CF3-C6H4)-pyrazol-3-yl 337 1-CB3, 5-(4-C(CH3)3-C6H4)-pyrazol-3-yl 15 338 1-CH3, 5-(4-CcH5-C6H~)-pyrazol-3-yl 339 1-CH3, 5-(2-Cl-C6H~)-pyrazol-3-yl 340 1-CH3, 5-(3-Cl-C6H~)-pyrazol-3-yl 341 1-CH3, 5-(4-Cl-C6~)-pyrazol-3-yl 342 1-CH3, 5-(2-Br-C6H~)-pyrazol-3-yl 20 343 1-CH3, 5-(3-~r-4H~)-pyrazol-3-yl 344 1-CH3, 5-(4-Br-C6H4)-pyrazol-3-yl 345 1-CH3, 5-(2-F-C6H4)-pyrazol-3-yl 346 1-CH3, 5-(3-F-C6H~)-pyrazol-3-yl 2 347 1-CH3, 5-(4-F-C6H4)-pyrazol-3-yl 348 1-c~3, 5-(2,4-C12-C6~3)-pyrazol-3-yl 349 1-CH3, 5-(2,5-Cl2-C6H3)-pyrazol-3-yl 350 1-CH3, 5-(2,6-C12-C6H3)-pyrazol-3-yl 351 l-CH3, 5-(3,4-C12-C6H3)-pyrazol-3-yl 30 352 1-CH3, 5-(2,4-F2-C6H3)-pyrazol-3-yl ~~-~ 353 1-CH3, 5-(2,5-F2-C6H3)-pyra201-3-yl 354 1-CH3, 5-(2,6-F2-C6H3)-pyrazol-3-yl 355 1-CH3, 5-(3,4-F2-C6H3)-pyrazol-3-yl 356 1-CH3, 5-(2-Cl, 5-OCH3-C6H3)-pyrazol-3-yl 357 1-CH3, 5-(2-Cl, 5-CH3-C6H 3 ) - pyrazol-3-yl 358 1-CH3, 5-(5-Cl, 2-OCH3-C6~3)-pyrazol-3-yl 359 1-CH3, 5-(5-Cl, 2-CH3-C6H3)-pyrazol-3-yl 360 1-CH3, 5-t2,5-(CH3)2-C6H3~-pyrazol-3-yl 40 361 3-CH3-;~o~zol-5-yl 362 3-CH(C~3)2-;Ro~701-5-yl 363 3-C(CH3)3-isoxazol-5-yl 364 3-cyclop~opyl-iQoxazol-5-yl 365 3-C6Hs-iRoxazol-5-yl 366 3-(2-CH3-C6H4)-; ROy~ 701 - 5-yl 367 3-(3-CH3-C6H4)-iQ~7ol-5-yl No. Het 368 3-(4-CH3-C6H~)-isoxazol-5-yl 369 3-(3-OCH3-C6H4)-i~nY~zol-5 5 370 3-(4-OCH3-C6~4)-isoxazol-5-yl 371 3-(4-N02-C6H~ qoY~7-01-5-yl 372 3-(3-No2-c6B4)-;~yA 701-5-yl 373 3-(4-CN-C6H4)-isoxazol-S-yl 374 3-(3-CN-C6H4)-isoxazol-5-yl 10 375 3-(3-CF3-C6H4)-i~oYA701-5-yl 376 3-(4-CF3-C6B~ oYA7ol-5 377 3-(4-C(CH3)3-C6H4)-i80YAzol-5 378 3-(4-C6H5-C6H4)-isoxazol-5-yl 379 3-(2-Cl-C6~4)-isoxazol-5-yl f 380 3-(3-Cl-C6~ oY~701-5-yl 381 3-(4-Cl-C6H4)-;~YA701-5-yl 382 3-(2-Br-C6H4)-;Qo~701-5-yl 383 3-(3-Br-C6H4)-isoxazol-5-yl 20 384 3-(4-Br-C6H4)-isoxazol-5-yl 385 3-(2-F-C6~ OYA701-5-Y1 386 3-(3-F-C6H~)-isoxazol-5-yl 387 3-(4-F-C6H4)-;~oY~701-5-yl 388 3-(2,4-C12-CcH3)-isoxazol-5-yl 389 3-(2,5-Cl2-C6H3)-isoxazol-5-yl 390 3-(2,6-C12-C6H3)-isoxazol-5-yl 391 3-(3,4-Cl2-C6~3)-;~Y~701-5-yl 392 3-(2,4-F2-C6H3)-;R~Y~701-5-yl 30 393 3-(2,5-F2-CGH3)-isoxa201-5-yl ~~~ 394 3-(2,6-F2-CcH3)-;~Y~7ol-5-yl 395 3-(3,4-F2-CcH3)-isoxazol-5-yl 396 3-(2-Cl, 5-OCH3-CcH3)-;~oY~zol-5-yl 397 3-(2-Cl, 5-CH3-C6H3)-i~oxazol-5-yl 398 3-(5-Cl, 2-OCH3-CcH3)-isoxazol-5-yl 399 3-(5-Cl, 2-CH3-C6H3)-iQoYA7ol-5 400 3-~2,5-(CH3)2-C6H3]-;noYA701-5-yl 401 3-CH3-4-Cl-isoxazol-5-yl 40 402 3-CH(C~3)2-4-Cl-~OYA701-5-yl 403 3-C(CH3)3-4-Cl-isoxazol-5-yl 404 3-cycl~ yl-4-cl-;~Y~7ol-5 405 3-C6H5-4-Cl-isoxazol-5-yl 406 3-(2-CH3-C6H4)-4-Cl-isoxazol-5-yl 407 3-(3-C~3-C6~)-4-Cl-;~oY~7~1-5-yl 408 3-(4-CH3-C6~4)-4-Cl-isoxazol-5-yl .
No. Het 409 3-(3-OC~3-CGH~)-4-C~ oxazol-5-y 410 3-(4-OCH3-C6H4)-4-Cl-isoxazol-5-yl 5 411 3-(4-NOz-CGH4)-4-Cl-isoxazol-5-yl 412 3-(3-N02-CGH4)-4-Cl-isoxazol-5-yl 413 3-(4-CN-CGH4)-4-Cl-iQ~YA7Ql-5-yl 414 3-(3-CN-CGH4)-4-Cl-;Q~YA7-ol-5-yl 415 3-(3-CF3-C6H~)-4-Cl-;-~oY~701-5-yl 10 416 3-(4-CF3-CGH41-4-Cl-~oY~7ol-5-yl 417 3-(4-C(CH3)3-C6H4)-4-cl-;QQYa~tQl-5-y 418 3-(4-CGH5-C6H4)-4-Cl-isoxazol-5-yl 419 3-(2-Cl-CGH4)-4-Cl-;soYA7ol-5-yl 420 3-(3-Cl-CGH~)-4-Cl-;Q~Y~7ol-5-yl ! 421 3-(4-Cl-C6H4)-4-Cl-;s~Y~ol-5-yl 422 3-(2-~r-C6H~)-4-Cl-isoxazol-5-yl 423 3-(3-Br-4H~)-4-Cl-~QoYa~Ql-5-yl 424 3-(4-Br-C6H~)-4-C~ oYAzol-5-yl 20 425 3-(2-F-C6H~)-4-Cl-isoxazol-S-yl 426 3-(3-F-CGH4)-4-Cl-isoxazol-5-yl 427 3-(4-F-C6H4)-4-Cl-iQoY~701-S-yl 428 3-(2~4-C12-CGH3)-4-Cl-isoxazol-5-yl 429 3-(2,5-C12-CG~3)-4-C1-;QOY~701-5-Y1 430 3-(2,6-C12-CGH3)-4-Cl-;QoY~Ql-5-yl 431 3-(3,4-C12-CGH3)-4-Cl-~QoYA~Ql-5-yl 432 3-(2,4-F2-C6H3)-4-Cl-;PoY~7Ql-5-yl 433 3-(2,5-F2-C6H3)-4-Cl-;R~Y~701-5-yl 30 434 3-(2,6-F2-C6H3)-4-Cl-;QoY~701-S-yl 435 3-(3,4-F2-C6H3)-4-Cl-iQn~7ol-5-yl 436 3-(2-Cl, 5-OCH3-C6H3)-4-Cl-i~oxazol-5-y 437 3-(2-Cl, 5-C~3-C6H3)-4-Cl-iQoY~7ol-5 438 3-(5-Cl, 2-OCH3-C6H3)-4-Cl-iQoYA~ol-5 439 3-(5-Cl, 2-CH3-C6H3)-4-Cl-isoxazol-5-yl 440 3~t2,5~(CH3)z-C6H3]-4-Cl-isoxazol-5-yl 441 5-CH3-isoxazol-3-yl 442 5-CH(CH3)2-isoxazol-3-yl 40 443 5-C(CH3)3-;QoY~701-3-yl 444 5-cycl~ ~l-iQ~701-3-yl 445 5-CGHs-isoxazol-3-yl 446 5-(2-CH3-CcH4)-isoxazol-3-yl 447 5-(3-CH3-C6H4)-isoxazol-3-yl 448 5-(4-CH3-CGH4)-isoxazol-3-yl 449 5-(3-OCB3-C6H~)-isoxazol-3-yl .
uv~
~ 217 21~9 i22 No. Het 450 5-(4-OCH3-C6H~ QoY~zol-3-yl 451 5-(4-N02-C6H4)-iQoxazol-3-yl 452 5-(3-N02-C6H4)-isoxazol-3-yl 453 5-(4-CN-C6~4)-isoxazol-3-yl 454 5-(3-CN-C6H4)-isoxazol-3-yl 455 5-(3-CF3-C6H~)-isoxazol-3-yl 456 5-(4-CF3-C6H~)-isoxazol-3-yl 457 5-(4-C(CH3)3-C6H4)-isoxazol-3-yl 458 5-(4-C6H5-C6~)-isoxazol-3-yl 459 5-(2-CI-C6H4)-i30xazol-3-yl 460 5-(3-Cl-C6H4)-isoxazol-3-yl 15 461 5-(4-Cl-C6H4)-;Qo~7~1-3-yl ! 462 5-(2-Br-C6H4)-;~Y~ol-3-yl 463 5-(3-Br-C6B4)-isoxazol-3-yl 464 5-(4-Br-C6H4)-;-8 n~ 701 -3-yl 465 5-(2-F-C6H~)-;QOY~Q1-3-Y1 ~ 20 466 5-(3-F-C6H4)-isoxazol-3-yl 467 5-(4-F-C6H~)-isoxazol-3-yl 468 5-(2,4-Cl2-C6H3)-~sx~70l-3-yl 469 5-(2,5-Cl2-C6H3)-isoxazol-3-yl 2 470 5-(2,6-C12-C6H3)-i~oxazol-3-yl 471 5-(3,4-Cl2-C6H3)-isoxazol-3-yl 472 5-(2,4-F2-C6H3)-isoxazol-3-yl 473 5-(2,5-F2-C6H3)-i QQY~ 7Ql - 3 - yl 474 5-(2,6-F2-C6H3)-isoxazol-3-yl 30 475 5-(3,4-F2-C6R3)-isoxazol-3-yl ~- 476 5-(2-Cl, 5-OCH3-C6H3)-; QOY~ 701-3-yl 477 5-(2-Cl, 5-CH3-C6H3)-i30xazol-3-yl 478 5-(5-Cl, 2-OCH3-C6H3)-i~Q~Y~zQl-3 ~ 479 5-(5-Cl, 2-CH3-C6H3)-isoxazol-3-yl 480 5-[2~5-(CH3)2-C6H3~-;QoY~7-01-3-yl 481 3-CH3-isothiazol-5-yl 482 3-CH(CH3)2-isothiazol-5-yl 483 3-C(CH3)3-isothiazol-5-yl 40 484 3-cyclo~ l-i80th;~ol-5-yl 485 3-C6H5-i~30thiazol-5-yl 486 3-(2-CH3-C6H~)-isothiazol-5-yl 487 3-(3-CH3-C6H4)-isothiazol-5-yl 488 3-(4-CH3-C6H~)-isothiazol-5-yl 489 3-(3-OCH3-C6H4)-i~othiazol-5-yl 490 3-(4-OCH3-C6H4)-isothiazol-5-yl 218 2199~
No. Het 491 3-(4-N02-C6H~)-isothiazol-5-yl 492 3-(3-N02-C6~ othiazol-5-yl 493 3-(4-CN-C6H4)-isothiazol-5-yl 494 3-(3-CN-C6H4)-isothiazol-5-yl 495 3-(3-CF3-C6H4)-isothiazol-5-yl 496 3-(4-CF3-CcH4)-isothiazol-5-yl 497 3-(4-C(CB3)3-C6B~)-isothiazol-5-yl 10 498 3-(4-C6H5-C6H4)-isothiazol-5-yl 499 3-(2-Cl-C6H~)-isothiazol-5-yl 500 3-(3-Cl-C6H4)-i~othiazol-5-yl 501 3-(4-Cl-C6B4)-isothiazol-5-yl 15 502 3-(2-Br-C6H4)-isothiazol-5-yl ~ 503 3-(3-Br-C6B~)-isothiazol-5-yl ( 504 3-(4-Br-C6H4)-isothiazol-5-yl 505 3-(2-F-C6H4)-isothiazol-5-yl 506 3-(3-F-C6H~)-isothiazol-5-yl 20 507 3-(4-F-C6H~)-isothiazol-5-yl 508 3-(2,4-Cl2-C6B3)-isothiazol-5-yl 509 3-(2,5-Cl2-C6H3)-isothiazoL-5-yl 510 3-(2,6-Cl2-C6H3)-isothiazol-5-yl 511 3-(3,4-Cl2-C6H3)-isothiazol-5-yl 512 3-(2,4-F2-C6B3)-isothiazol-5-yl 513 3-(2,5-F2-C6R3)-isothiazol-5-yl 514 3-(2,6-F2-C6B3)-isothiazol-5-yl 515 3-(3,4-F2-C6B3)-isothiazol-5-yl 30 516 3-(2-Cl, 5-oCR3-C6H3)-isot h; ~ 70 1 - 5-yl ,_ 517 3-(2-Cl, 5-CB3-C6B3)-isothiazol-5-yl 518 3-(5-Cl, 2-OC83-C6H3)-isothiazol-5-yl 519 3-(5-Cl, 2-CH3-C6H3)-isothiazol-5-yl 520 3-t2,5-(CB3)2-C6H3]-isothiazol-5-yl 521 2-CH3-oxazol-4-yl 522 2-CB(CH3)2-oxazol-4-yl 523 2-C(CH3)3-oxazol-4-yl 524 2-cyclv~ yl-oxazol-4-yl 40 525 2-C6H5-oxazol-4-yl 526 2-(2-CH3-C6H4)-oxazol-4-yl 527 2-(3-CH3-C6H~)-oxazol-4-yl 528 2-(4-CH3-C6H4)-oxazol-4-yl 529 2-(3-OCH3-C6H~)-oxazol-4-yl 530 2-(4-OCH3-C6H~)-oxazol-4-yl 531 2-(4-N02-C6H~)-oxazol-4-yl ~99~22 No. Het 532 2-(3-NO2-CcH4)-oxazol-4-yl 533 2-(4-CN-C6H~)-oxazol-4-yl 5 534 2-(3-CN-C6H4)-oxazol-4-yl 535 2-(3-CF3-C6H4)-oxazol-4-yl 536 2-(4-CF3-C6H4)-oxazol-4-yl 537 2-(4-C(CH3)3-C6H~)-oxazol-4-yl 538 2-(4-C6Hs-C6H~)-oxazol-4-yl 10 539 2-(2-Cl-C6H4)-oxazol-4-yl 540 2-(3-Cl-C6H~)-oxazol-4-yl 541 2-(4-C~-C6H4)-oxazol-4-yl 542 2-(2-Br-C6H~)-oxazol-4-yl 543 2-(3-Br-C6H4)-oxazol-4-yl 2--(4-Br-C6H4)-oxazol--4--yl 545 2-(2-F-C6B 4 ) - oxazol-4-yl 546 2-(3-F-C6H4)-oxazol-4-yl 547 2-(4-F-C6H~)-oxazol-4-yl 20 548 2-(2,4-cl2-c6~3)-oxazol-4-yl 549 2-(2,5-Cl2-C6R3)-oxazol-4-yl 550 2-(2,6-Cl2-C6H3)-oxazol-4-yl 551 2-(3,4-C12-C6H3)-oxazol-4-yl 2 552 2-(2,4-F2-C6H3)-oxazol-4-yl 553 2-(2,5-F2-C6H3)-oxazol-4-yl 554 2-(2,6-F2-C6H3)-oxazol-4-yl 555 2-(3,4-F2-CcH3)-oxazol-4-yl 556 2-(2-Cl, 5-OCH3-C6H3)-oxazol-4-yl 30 557 2-(2-Cl, 5-CH3-C6H3)-oxazol-4-yl 558 2-(5-Cl, 2-OCH3-CcH3)-oxazol-4-yl 559 2-(5-Cl, 2-CH3-C6H3)-oxazol-4-yl 560 2-t2,5-(CH3)2-CcH3l-oxazol-4-yl 561 2-CH3-thiazol-4-yl 562 2-CH(CH3)2-thiazol-4-yl 563 2-C(CH3)3-thiazol-4-yl 564 2-cyclo~ ~yl-thiazol-4 565 2-CcH5-thiazol-4-yl 40 566 2-(2-CH3-CcH4)-thiazol-4-yl 567 2-(3-CH3-CcH~)-thiazol-4-yl 568 2-(4-CH3-CcH~)-thiazol-4-yl 569 2-(3-OCH3-CcH4)-thiazol-4-yl 570 2-(4-OCH3-CcH4)-thiazo1-4-yl 571 2-(4-NO2-C6H4)-thiazol-4-yl 572 2-(3-NO2-CcH4)-thiazol-4-yl .
00~0/45204 ~ 2199 122 No. Het 573 2-(4-CN-C6H4)-th~ ~701 -4-yl 574 2-(3-CN-C6H~)-th; ~701 -4-yl 575 2-(3-CF3-C6H4)-thiazol-4-yl 576 2-(4-CF3-C6H4)-thiazol-4-yl 577 2-(4-C(CH3)3-C6H4)-thiazol-4-yl 578 2-(4-C6H5-C6H4)-thiazol-4-yl 579 2-(2-Cl-C6H4)-thiazol-4-yl 580 2-(3-Cl-C6H4)-thiazol-4-yl 581 2-(4-Cl-CcH4)-thiazol-4-yl 582 2-(2-Br-C6~4)-thiazol-4-yl 583 2-(3-Br-C6H4)-thiazol-4-yl 584 2-(4-Br-C6H~)-thiazol-4-yl 585 2-(2-F-C6H~)-thiazol-4-yl 586 2-(3-F-C6H~)-thiazol-4-yl 587 2-(4-F-C6H~)-thiazol-4-yl 588 2-(2,4-C12-C6H3)-thiazol-4-yl 589 2-(2,5-C12-C6H3)-thiazol-4-yl 590 2-(2,6-C12-C6H3)-~h; ~701 - 4-yl 591 2-(3,4-C12-CcH3)-thiazol-4-yl 592 2-(2,4-F2-C6H3)-thiazol-4-yl 593 2-(2,5-F2-CcB3)-thiazol-4-yl 594 2-(2,6-F2-C6H3)-thiazol-4-yl 595 2-(3,4-F2-C6H3)-thiazol-4-yl 596 2-(2-Cl, 5-OCH3-C6H3)-thiazol-4-yl 597 2-(2-Cl, 5-CH3-C6H3)-thiazo1-4-yl 30 598 2-(5-Cl, 2-OCH3-C6H3)-thiazol-4-yl 599 2-(5-Cl, 2-CH3-C6H3)-thiazol-4-yl 600 2-~2,5-(CH3)2-C6H3]-thiazol-4-yl 601 1,3-(CH3)2-1,2,4-triazol-5-yl 602 1-CH3, 3-CH( CH3 ) 2 - 1, 2,4-triazol-5-yl 603 l-CH3, 3-C(CH3)3-1,2,4-triazol-5-yl 604 l-CH3, 3-cyclopropyl-1,2,4-triazol-5-yl 605 1-CH3, 3-C6Hs-1,2,4-triazol-5-yl 606 1-CH3, 3-(2-CH3-C6H~)-1,2,4-triazol-5-yl 607 l-CH3, 3-(3-CB3-CcH~)-1,2,4-triazol-5-yl 608 1-CH3, 3-(4-CH3-C6H~)-1,2,4-triazol-5-yl 609 1-CH3, 3-(3-OCH3-C6H4)-1,2,4-triazol-5-yl 610 1-CH3, 3-(4-OC~3-C6H4)-1,2,4-triazol-5-yl 611 l-CH3, 3-(4-NO2-C6H4)-1,2,4-triazol-5-yl 612 1-CH3, 3-(3-NO2-C6H~)-1,2,4-triazol-5-yl 613 l-CH3, 3-(4-CN-C6H~)-1,2,4-triazol-5-yl 2199~22 No. ~et 614 1-CH3, 3-~3-CN-C6H4)-1,2,4-triazol-5-yl 615 1-CH3, 3-(3-CF3-C6H~)-1,2,4-triazol-5-yl 616 1-CB3, 3-(4-CF3-C6~4)-1,2,4-triazol-S-yl 617 1-CH3, 3-(4-C(C~3)3-C6H4)-1,2,4-triazol-5-yl 618 1-CH3, 3-(4-C6H5-C6H4)-1,2,4-triazol-5-yl 619 1-Ca3, 3-(2-Cl-C6H4)-1,2,4-triazol-5-yl 620 1-CH3, 3-(3-Cl-C6H4)-1,2,4-triazol-S-y 10 621 1-CH3, 3-(4-Cl-C6H4)-1,2,4-triazol-5-yl 622 1-CH3, 3-(2-Br-C6B~)-1,2,4-triazol-S-yl 623 1-CH3, 3-(3-Br-C6H~)-1,2,4-triazol-5-yl 624 1-CH3, 3-(4-Br-C6~)-1,2,4-triazol-S-y 625 1-CH3, 3-(2-F-C6~4)-1,2,4-triazol-S-yl 1-CR3, 3-(3-F-C684)-1,2,4-triazol-S-yl 627 1-CH3, 3-(4-F-C6H4)-1,2,4-triazol-S-yl 628 1-CH3, 3-(2,4-C12-C6H3)-1,2,4-triazol-5-yl 629 1-CH3, 3-(2,5-C12-C6H3)-1,2,4-triazol-S-yl 20 630 1-C83, 3-(2,6-C12-C6H3)-1,2,4-triazol-S-yl 631 1-CH3, 3-(3,4-C12-C6H3)-1,2,4-triazol-5-yl 632 1-CH3, 3-(2,4-F2-C6H3)-1,2,4-triazol-S-yl 633 1-CH3, 3-(2,5-F2-C6H3)-1,2,4-triazol-5-yl 634 1-CH3, 3-(2,6-F2-C6H3)-1,2,4-triazol-5-yl 635 1-CH3, 3-(3,4-F2-C6H3)-1,2,4-triazol-5-yl 636 1-CH3, 3-(2-Cl, 5-OCH3-C6H3)-1,2,4-triazol-S-yl 637 1-CH3, 3-(2-Cl, 5-CH3-C6H3)-1,2,4-triazol-5-yl 638 1-CH3, 3-(S-Cl, 2-OCH3-C6B3)-1,2,4-triazol-5-yl 30 639 1-CH3, 3-(5-Cl, 2-CH3-C6H3)-1,2,4-triazol-5-yl 640 1-CH3, 3-~2,5-(CH3)2-C6H3]-1,2,4-triazol-S-yl 641 5-CH3-1,3,4-QYA~;A7ol-2-yl 642 5-CH(C~3)2-1,3,4-oYA~;A7Ql-2-yl 643 5-C(CH3)3-1,3,4-o~A~;A7ol-2-yl 644 5-cyclo~L~1-1,3,4-nY~;A7ol-2 yl 645 5-C6H5-1,3,4-oY~ 7.ol-2-yl 646 5-(2-CH3-C6H4)-1,3,4-oYA~;A7ol-2-yl 647 5-(3-C~3-C6H4)-1,3,4-nYA~;A7ol-2-yl 40 648 5-(4-CB3-C6H4)-1,3,4-oYA~;A7ol-2-yl 649 5-(3-OCH3-C6H4)-1~3,4-~YA~iA7ol-2-yl 650 5-(4-OCH3-C6H4)-1,3,4-nYA~;A7ol-2-yl 651 5-(4-N02-C6H4)-1,3,4-oYA~;A~Ql-2-yl 652 5-(3-N02-C6H4)-1,3,4-QYA~; A 7Ql-2-yl 653 5-(4-CN-C6~4)-1,3,4-oYA~;A7-ol 2 yl 654 5 (3 CN-C6~4) 1,3,4 ~yA~;A~Ql 2 yl .
2199 1~2 No. 8e~
655 5-(3-CF3-C6H4)-1,3,4-oYA~; A ~701-2-yl 656 5-~4-CF3-C~H~)-1,3,4-n~;A 701- 2-yl 657 5-(4-c(cH3)3-c6H4)-l~ 3~4-nY~;A701-2-658 5-(4-C6Hs-C6~)-1,3,4-oYA~i~7Ol-2-yl 659 5-(2-C1-C6H4)-1,3,4-O~Y~;A7Q1-2-Y1 660 5-(3-Cl-C6H4)-1,3,4 ~yA~;A7ol 2 yl 661 5-(4-Cl-C6H4)-1,3,4-nYA~;A 7-ol- 2-yl 0 662 5-(2-Br-C6~4)-1,3,4-oYAd;A7ol-2-yl 663 5-(3-Br-CcH4)-1,3,4-~YA~A.7Ol-2-y 664 5-(4-B~-ccH4)-lr3r4-~yA~;A7Ql-2 665 5-(2-F-C6H~)-1,3,4-oY~; A701- 2-yl 15 666 5-(3-F-C6H4)-1,3,4-o~A~iA7Ql-2-yl 667 5-(4-F-C6H~)-1,3,4-o~; A701-2-yl 668 5-( 2,4-C12-C6H3)-1, 3~4-oYA~;A7ol-2-yl 669 5-( 2r 5-C12-C6H3)-1,3,4-nY~;A 701- 2-yl 670 5-( 2r 6-C12-C6H3)-1,3,4-nYA~; A701- 2-yl 20 671 5-(3,4-C12-C6H3)-1,3,4-ox~A;A 701-2-yl 672 5-(2,4-F2-C6H3)-1,3,4-nYA~;A7ol-2-yl 673 5-(2,5-F2-C6H3)-1, 3, 4-oY~; A ~ol-2-yl 674 5-(2,6-F2-C6H3)-1,3,4-nYA~;A7Ol-2-yl 675 5-(3,4-F2-C6H3)-1,3 r 4 - oYA~ ~701-2-yl 676 5-( 2-C1~ 5-OCH3-C6H3)-1~ 3,4-oY~A7ol-2-yl 677 5-(2-Cl, 5-CH3-C6H3)-1,3,4-oYA~;A7ol-2-yl 678 5-(5-Cl, 2-OCH3-C6H3)-l, 3r4-oYA~i~Ql-2 679 5-(5-Cl, 2-CH3-C6H3)-1,3,4-QYA.~;A 701- 2-yl 30 680 5-[2,5-(CH3)2-C6H3]-1,3,4-o,Y,~;A7ol-2-yl 681 5-CH3-1,2,4- O~A~;A701- 3-yl 682 5-CH(CH3)2-1,2,4-~Y~; A701- 3-yl 683 5-C(CH3)3-1,2,4-oYa~A7ol-3-yl 684 5-cyclopropyl-1,2,4-ox,~;A7ol-3-yl 685 5-C6Hs-1,2,4-nxAA;A 7-ol-3-yl 686 5-(2-CH3-C6Hq)-1,2,4-nY~;A7ol-3-yl 687 5-(3-CH3-C6H4)-1,2,4-~A~;A7ol-3-yl 688 5-(4-CH3-C6H~)-1,2,4-nY~ 7Ql-3-yl 40 689 5-(3-OCH3-CCH4)-1,2,4-oyA~;~7ol-3-yl 690 5-(4-OCH3-CcH4)-1,2,4-nYA~;A7ol-3-yl 691 5-(4-NO2-CCH4)-l, 2~ 4-o,YA~;A7ol-3-yl 692 5-(3-NO2-C6H4)-1,2,4-oY~;A7ol-3-yl 693 5-(4-CN-C6H4)-1,2,4-oY~;A7ol-3-yl 694 5-(3-CN-C6H4)-1,2,4-oxadiazol-3-yl 695 5-(3-CF3-C6H4)-1,2,4-oYA~i~7ol-3-yl =~_ 2 1 9 9ll 2 2 No. ~et 696 5-(4-CF3-C6~4)-1,2,4-~Y~;A701-3-y 697 5-(4-C(C~3)3-C6H4)-1,2,4-~Ya~;AZol-3 5 698 5-(4-C6Hs-C6H4)-1,2~4-oYAA;A~ol-3 699 5-(2-C1-C6H4)-1,2,4-OYA~;A7Q1-3-Y1 700 5--(3--Cl--C6H4)--1~2~4--oyA~l;a7ol--3--yl 701 5_(4_C1_C6H4)_1,2,4_0~;A 701 - 3-yl 702 5-(2-Br-C6~4)-1,2,4-oY4~;A7Ql-3-y 10 703 5-(3-~r-C6R4)-1,2,4-n~;Azol-3-yl 704 5-(4-Br-CcH4)-1,2,4-oYA~; A zQl-3-yl 705 5-(2-F-C6~4)-1,2,4-~Y4A;A7ol-3 706 5-(3-F-C6B4)-1,2,4-oY~;A7ol-3-y 15 707 5-(4-F-C6H~)-1,2,4-oYaA;A7ol-3 708 5-(2~4-cl2-c6H3)-l~2~4-~Ya~;A~Ql-3 709 5-(2,5-C12-C6H3)-1,2,4-o~a~ A 701-3-yl 710 5-(2,6-C12-C6H3)-1,2,4-OY~;A7O1-3-Y1 711 5-(3,4-C12-C6H3)-1,2,4-oxadiazol-3-y 20 712 5-(2,4-F2-C6H3)-1,2,4-~YA~; A701 - 3-yl 713 5-(2,5-F2-C6H3)-1,2,4-~YA~;A7ol-3-y 714 5-(2,6-F2-C6H3)-1,2,4-oYa~a7ol-3-y 715 5-(3,4-F2-C6H3)-1,2,4-~Y4~a7ol-3-y 2 716 5-(2-Cl, 5-OCH3-C6H3)-1,2,4-~Y~;A7ol-3-y 717 5-~2-Cl, 5-CH3-C6H3)-1,2,4-~YA~; A 701-3-yl 718 5-(5-Cl, 2-OCH3-C6~3)-1,2,4-~Y~;A701-3-yl 719 5-~5-Cl, 2-C~3-C6H3)-1,2,4-oY4~;A7o1-3-yl 720 5-t2,5-(C~3)2-C6H3~-1,2,4-oY~;A7ol-3-yl 30 721 3-CH3-1,2,4-~Y~la7ol-5-y 722 3-cH(cH3)2-l~2~4-oy~n7Ql-5 723 3-C(CH3)3-1,2,4-oYA~;A~Ql-5-yl 724 3-cyclG~ l-1,2,4-oY~;A7Ql-5-yl 725 3-C6H5-1,2,4-oY4~;A 701 - 5 - yl 726 3-(2-CH3-CcH4)-1,2,4-oYa~;A?ol-5-yl 727 3-(3-CH3-C6H4)-1,2,4-oY~ 701 - 5-yl 728 3-(4-CH3-C6H4)-1,2,4-oYA~;A7ol-5 729 3-(3-ocH3-c6H4)-l~2~4-~YA~;A7Q
40 730 3-(4-OCH3-C6H~)-1,2,4-nYa~;A7ol-5-y 731 3-(4-N02-C6Hg)-1,2,4-ox~iA7ol-5-yl 732 3_(3_NO2_C6~4)_1,2,4_0Y~;A~701_5_Y1 733 3-(4-CN-4 H~)-1,2,4-~Ya~;4.7ol-5-yl 734 3-(3-CN-C6H4)-1,2,4-~Y~;~7ol-5-yl 735 3-(3-CF3-C6H4)-1,2,4-oxadiazol-5-yl 736 3-(4-CF3-C6H4)-1,2,4-oYA~;Azol-5-yl 2199~22 No. Het 737 3-(4 C(cH3)3-c6H4)-l~2~4-~yA~7ol-5 738 3-(4-c6H5-c6H4)-l~2~4-oAy~ A~ ol-5-yl 739 3-(2-Cl-C6Hq)-1,2,4-oY~;A7ol-5-yl 740 3-(3-Cl-C6H4)-1,2,4-oY. A~; A70l-5-yl 741 3-(4-Cl-C6H4)-1,2,4-oY~A~;A7Ql-5 742 3-(2-Br-C6H4)-1,2,4-oYA~iA7ol-5-yl 743 3-(3-~3r-C6H4)-1,2 ~ 4 - OyA~ i A 701-5-yl 744 3-(4-Br-C6H4)-1,2,4-oYA~;A7Ql-5 745 3-(2-F-C6~4)-1,2,4-oY~i A 7~1-5-yl 746 3-(3-F-C6~)-1,2,4-o-Y~;A7Ql-5-yl 747 3-(4-F-C6H4)-1,2,4-oYA~iA7ol-5-yl 748 3-(2,4-Cl2-C6H3)-1,2,4-oYAA;A7ol-5 ~~ 749 3-(2,5-Cl2-C6H3)-1,2,4-nY~ 7-ol-5-y 750 3-(2,6-Cl2-C6H3)-1,2,4-nX~iA7Ql-5-yl 751 3-(3,4-Cl2-C6H3)-1,2,4-oYA~i~.7ol-5-yl 752 3-(2,4-F2-C6H3)-1,2,4-oY~;A-7ol-5-yl 20 753 3-(2,5-F2-C6H3)-1,2,4-oYA~;A7ol-5-yl 754 3-~2,6-F2-C6H3)-1,2,4-oYA~;A7-ol-5-yl 755 3 (3,4 F2-C6H3) 1,2,4-oYA~;A7ol 5 yl 756 3-(2-Cl, 5-OCH3-C6H3)-1,2,4-oYA~;A701-5-yl 757 3-(2-Cl, 5-CH3-C6R3)-1,2,4-nYA~A; A 701 - 5-yl 758 3-(5-Cl, 2-OCH3-C6H3)-1,2,4-oY~ 701-5-yl 759 3-(5-Cl, 2-CH3-C6H3)-1,2,4-nY~iA701-5-yl 760 3-t2~5-(CH3)2-C6~3]-1,2 ~ 4 - OYA~ i A 701-5-yl 761 5-CH3-1,2,4- th; A~;A701-3-yl 30 762 5-CH(CH3)2-1,2,4-~h;~i~A~ol-3-yl 763 5-C(CH3)3-1,2,4-~h;~ 701-3-yl 764 5-cyclopropyl-1,2,4-th;~;A7ol-3-yl 765 5-C6Hs-l~2~4-~h i A~;~ 701 - 3-yl 766 5-(2-CH3-C6H~)-1,2,4-th;~;A701-3-yl 767 5-(3-CH3-C6H4)-1,2,4-thiA~;A7ol-3-yl 768 5-(4-CH3-4H~)-1, 2, 4 - ~h ~ 701-3-yl 777 5-(3-OCH3-C6H~)-1, 2, 4-~h; A~i A 701-3-yl 770 5-(4-OCH3-C6H~)-1,2,4-~h;A~iA7~l-3 40 771 5-(4-N02-C6H4)-1,2,4-~h;~;~701-3-yl 772 5-(3-N02-C6H~)-1,2,4-~h~ 701-3-yl 773 5-(4-CN-C6H~)-1,2,4-~h i ~ ol-3-yl 774 5-(3-CN-C6H~)-1,2,4-th;~;A701-3-yl 775 5-(3-CF3-C6H4)-1,2,4-th;A~;~701-3-yl 776 5-(4-CF3-C6H~)-1,2,4-~h; ~A,~; A70l - 3 - yl 777 5-(4-C(CR3)3-C6H4)-1,2,4-~h~A~;A701-3-yl .
0050/45Z04 ' ~.',~v 225 2 1 9 9 ~ 2 2 No. Het 778 5-(4-C6Hs-C6B4)-1,2,4-~h;A~;A7Ol-3-yl 779 5-(2-Cl-C6H4)-1,2,4-thiAAiA7Ol-3-y 780 5-(3-Cl-C6H4)-1,2,4-th;~A7Ol-3-yl 781 5-(4-Cl-C6B4)-1~2~4-th; ~A~i A701-3-yl 782 5-(2-Br-C6H4)-1,2,4-~h;~;A7Ol-3 783 5-(3-Br-c6H4)-lr2~4-thi~;A7ol-3-yl 784 5-(4-~3r-C6H4)-1,2,4-th;A~;A~ol-3-yl 10 785 5-(2-F-C6H4)-1,2,4-~h.~A~;~7cl-3-yl 786 5-(3-F-C6H~)-1,2,4-~h;~;~701-3-yl 787 5-~4-F-C6H~)-1,2,4-th;A~;~7Ol-3 788 5-(2~4-clz-c6H3)-l~2,4-th~A~;~7Ql-3 15 789 5-(2,5-C12-C6H3)-1,2,4-th~;AZol-3-yl 790 5-(2,6-Cl2-C6H3)-1,2,4-~h;~;~7Ol-3-yl 791 5-(3,4-Cl2-C6H3)-1,2,4-~h;A~;~7Ol-3 792 5-(2,4-F2-C6H3)-1,2,4-th;~; A 701-3-yl 793 5-(2,5-FZ-C6H3)-1,2,4-th;A~iA7ol-3 20 794 5-(2,6-F2-C6H3)-1,2,4-th;A~;A7Ol-3 795 5-(3,4-F2-C6R3)-1~2,4-~h; A~; A ~701 - 3-yl 796 5-(2-C1~ 5-OCH3-C6H3)-1~2~4-th; A~; A 7~1- 3 - yl 797 5-(2-C1~ 5-CH3-C6H3)-1~2~4-~h; A~; A P01 - 3 - yl 798 5-(5-Cl~ 2-OCH3-C6H3)-1,2,4-th;A~;~701-3-yl 799 5-(5-C1~ 2-CH3-C6H3)-1~2~4-~h; A~; A70l - 3 - yl 800 5-~2,5-(CH3)2-C6H3]-1,2,4-th;A~;A7Ol-3 801 5-CH3-1,3,4-~hi A~; A7Ql - 2 - yl 802 5-CH(CH3)2-1,3,4-th;A~;A7Ol-2 30 803 5-C(CH3)3-1,3,4-~h;A~;A~1-2-yl 804 5-cyclG~ v~yl~l~3~4~thiA~;A7-Ol-2 805 5-C6Hs-1,3,4-thiadiazol-2-yl 806 5-(2-CH3-C6H4)-1,3,4-~h~A~;A7Ol-2-yl 807 5-(3-CH3-C6H4)-1,3~4-~h; A~ ~ A 701 - 2-yl 808 5-(4-CH3-C6H4)-1~3~4-~h;~ z701 - 2-yl 809 5-(3-OCH3-C6H4)-1,3,4-th;~;~7ol-2-yl 810 5-(4-OCH3-C6H4)-1,3~4-th;A~ 701 - 2-yl 811 5-(4-NO2-C6H4)-1,3,4-~h;A~;A7Ol-2-yl 40 812 5-(3-NO2-C6H4)-1~3~4-~h; A~; AZQl - 2 - yl 813 5-(4-CN-C6H~)-1,3,4-th;A~;R7Ol-2 814 5-(3-CN-C6H~)-1,3,4-thi~;A7ol-2 815 5-(3-CF3-C6H4)-1,3,4-thi~;A~cl-2-yl 816 5-(4-CF3-C6H4)-l~ 3~ 4-th~ A~; A70l - 2 - yl 817 5-(4-C(CH3)3-C6H4)-1,3,4-~h~;AZol-2 818 5~(4~C6Hs~C6H4)-1,3,4-th;a~zol-2-yl UU~ 3~U~
~ 226 ~99122 No. Het 819 5-(2 Cl-C6H4)-1,3,4-~h; A~i A701 2 yl 820 5-(3-Cl-C6~4)-1,3, 4 - th i ~ i A 701-2-yl 5 821 5-(4-Cl-C6H4)-1,3,4-thi A~i A 701-2-yl 822 5-(2-Br-C6H4)-1,3,4-~hi~; A 701 - 2 - yL
823 5-(3-.8r-CcH4)-1,3,4-th;~; A zol-2-yl 824 5-(4-Br-C6H4)-1,3,4-thi~iA7ol-2 825 5-(2-F-C6H~)-1,3,4-th;A~;A7ol-2-yl 10 826 5-(3-F-C6H4)-1,3,4-th;A~iA701-2-yl 827 5-(4-F-C6H~)-1,3,4-th;~;~701-2-yl 828 5-(2~4-cl2-c6H3)-l~3~4-thi A~; A 701-2-yl 829 5-(2~5-cl2-c6H3)-l~3~4-~h~ A~ A7~1 - 2 -15 830 5-(2,6-C12-CCH3)-1~3~4-~h;A~Ql-2-yl f 831 5-(3,4-C12-C6H3)-1,3,4-th; A~ ol-2-yl 832 5-(2,4-F2-C6H3)-1,3,4-~h;A~;A7ol-2-yl 833 5-(2,5-F2-C6H3)-1,3,4-th;A~;A701-2-yl 834 5-(2,6-F2-C6H3)-1,3,4-~h;A~;AZol-2 20 835 5-(3,4-F2-C6H3)-1,3,4-th;A~;A701-2-yl 836 5-(2-Cl, 5-ocH3-ccH3)-l~3~4-th;A~;Azol-2 837 5-(2-Cl, 5-cH3-c6H3)-l~3~4-th;~;A7ol-2 838 5-(S-Cl, 2-OCH3-C6H3)-1,3,4-~h;A~iA7ol-2 839 5-(5-Cl, 2-CH3-C6H3)-1,3,4-~hi ~A; A701 - 2 - yl 840 5-t2~5-(cH3)2-c6H3]-l~3~4-~h;~ 7ol-2 841 1,3-(CH3)2-pyrazol-4-yl 842 3-CH3, 1-CH(CH3)2-pyrazol-4-yl 843 3-CH3, l-C(CH3)3-pyrazol-4-yl 30 844 3-CH3, l-cyclop o~yl-pyrazol-4 845 3-CH3, 1-C6H5-pyrazol-4-yl 846 3-CH3, 1-(2-CH3-C6H4)-pyrazol-4-yl 847 3-CH3, 1-(3-CH3-C6H~)-pyrazol-4-yl 848 3-CH3, 1-(4-CH3-C6H~)-pyrazol-4-yl 849 3-CH3, 1-(3-OCH3-C6H4)-pyrazol-4-yl 850 3-CH3, 1-(4-OCH3-C6H4)-pyrazol-4-yl 851 3-CR3, 1-(4-N02-C6H4)-pyrazol-4-yl 852 3-CH3, 1-(3-N02-C6H~)-pyrazol-4-yl 40 853 3-CH3, 1-(4-CN-C6H~)-pyrazol-4-yl 854 3-CH3, 1-(3-CN-C6H~)-pyrazol-4-yl 855 3-CH3, 1-(3-CF3-C6H~)-pyrazol-4-yl 856 3-CH3, l-(4-CF3-C6H~)-pyrazol-4-yl 857 3-CH3, 1-(4-C(CH3)3-C6H4)-pyrazol-4-yl 858 3-CH3, 1-(4-C6H5-C6H4)-pyrazol-4-yl 859 3-CH3, l-(2-Cl-C6H~)-pyrazol-4-yL
0050/452~4 -227 2199~22 No. Het 860 3-CH3, 1-(3-Cl-CcH4)-pyrazol-4-yl 861 3-CR3, 1-(4-Cl-C6H4)-pyrazol-4-yl 862 3-CH3, 1-(2-~r-C6H4)-pyrazol-4-yl 863 3-CH3, 1-(3-}3r-C6H~)-pyrazol-4-yl 864 3-CH3, 1-(4-Br-C6H4)-pyrazol-4-yl 865 3-CH3, 1-(2-F-C6H~)-pyrazol-4-yl 866 3-CH3, 1-(3-F-C6H~)-pyrazol-4-yl 867 3-CH3, 1-(4-F-C6H4)-pyrazol-4-yl 868 3-CH3, 1-(2,4-C12-C6H3)-pyrazol-4-yl 869 3-CH3, 1-(2,5-C12-C6H3)-pyrazol-4-yl 870 3-CH3, 1-(2,6-C12-C6H3)-pyrazol-4-yl 871 3-CH3, 1-(3,4-C12-C6H3)-pyrazol-4-yl f 872 3-CH3, 1-(2,4-F2-C6H3)-pyrazol-4-yl 873 3-CH3, 1-(2,5-F2-C6H3)-pyrazol-4-yl 874 3-CH3, l-(2,6-F2-C6H3)-pyrazol-4-yl 815 3-CH3, 1-(3~4-F2-c6H3)-pyrazol-4-yl 876 3-CH3, 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 877 3-CH3, 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 878 3-CH3, 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 879 3-CH3, 1-(5-Cl, 2-CH3-C6H3)-pyrazol-4-yl 880 3-CH3, 1-[2,5-(CH3)2-C6H3]-pyrazol-4-yl 881 3,5-(CH3)2, 1-C6Hs-pyrazol-4-yl 882 3,5-(CH3)2, 1-(2-CH3-C6H4)-pyrazol-4-yl 883 3~5-(C~3) 2 ~ 1 - (3-cH3-c6H4)-pyrazol-4 884 3,5-(CH3)2, 1-(4-CH3-C6H4)-pyrazol-4-yl 885 3~5-(CH3) 2 ~ 1 - ( 3-ocH3-c6H4)-pyrazol-4 886 3~5-(CH3) 2 ~ 1 - ( 4-ocH3-c6H~)-pyrazol-4 887 3,5-(CH3)2, 1-(4-NO2-C6H~)-pyrazol-4-yl 888 3,5-(CH3)2, 1-(3-No2-c6H~)-pyrazol-4 889 3,5-(CH3) 2 ~ 1 - ( 4-CN-C6H~)-pyrazol-4-yl 890 3,5-(CH3)2, 1-(3-CN-C6H~)-pyrazol-4-yl 891 3,5-(CH3)2, 1-(3-cF3-4H4)-pyrazol-4 892 3~5-(CH3) 2 ~ 1 - ( 4-cF3-c6H4)-pyrazol-4-yl 893 3,5-(CH3)2, 1-(4-C(CH3)3-C6H~)-pyrazol-4-yl 894 3,5-(CH3)2, 1-(4-C6H5-C6H~)-pyrazol-4-yl 895 3,5-(CH3)2, 1-(2-Cl-C6H~)-pyrazol-4-yl 896 3,5-(CH3)2, 1-(3-Cl-C6H~)-pyrazol-4-yl 897 3,5-(CH3)2, 1--(4--Cl--C6H4)--pyrazol--4--yl 898 3,5-(CH3) 2 ~ 1 - ( 2-Br-C6H~)-pyrazol-4-yl 899 3,5-(CH3) 2 ~ 1 - (3-Br-C6H~)-pyrazol-4-yl 900 3,5-(CH3)2, 1-(4-Br-C6H~)-pyrazol-4-yl uu~u ~ ~v~
2~99 122 No. Het 901 3,5-(CH3)2, 1-(2-F-C6H4)-pyrazol-4-yl 902 3,5-(CH3)2, 1-(3-F-C6H~)-pyrazol-4-yl 903 3,5-(CH3)2, 1-(4-F-C6H4)-pyrazol-4-yl 904 3,5-(CH3)2, 1-(2,4-C12-C6H3)-pyrazol-4-yl 905 3,5-(C~3)2, 1-(2~5-cl2-c6H3)-pyrazol-4-yl 906 3,5-(CH3)2, 1-~2,6-Cl2-C6H3)-pyrazol-4-yl 907 3,5-(C~3)2, 1-(3~4-Cl2-C6H3)-pyrazol-4-yl 10 908 3,5-(CH3)2, 1-(2,4-F2-C6H3)-pyrazol-4-yl 909 3,5-(CH3)2, 1-(2,5-F2-C6H3)-pyrazol-4-yl 910 3,5-(CH3)2, 1-(2~6-F2-C6H3)-pyrazol-4-yl 911 3~5--(CH3)2~ 1--(3~4--F2--C6H3)--pyrazol--4-yl 15 912 3,5-(CH3)2, 1-(2-Cl, 5-OCH3-C6H3)-pyrazol-4-yl 913 3,5-(CR3)2, 1-(2-Cl, 5-CH3-C6H3)-pyrazol-4-yl 914 3,5-(C~3)2, 1-(5-Cl, 2-OCH3-C6H3)-pyrazol-4-yl 915 3,5-(CH3)2, 1-(5-Cl, 2-CH3-C683)-pyrazol-4-yl 916 3~5-(CH3)2~ 2~5-(c83)2-c6H3]-pyrazol-4 gO
-229 2~99-;122 Table 779 CG~ OU11dS of the general formula I.B (n = 0) in which UR' i8 5 methoxy, VR" is methoxy, yb is oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 780 10 Co...p~lds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is methoxy, yb iS oxygen and Ab for a ~oh.~oulld corresponds to one of the groups ~tated in Table E
Table 781 ( Co.. pounds of the general formula I.B ~n = 0) in which UR' i8 methoxy, VR" is ethoxy, yb is oxygen and Ab for a ~v~ ound corresponds to one of the ~LU~S stated in Table E
20 Table 782 Co...~oul,ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethoxy, yb i8 oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 783 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is methoxy, yb is oxygen and Ab for a co~ ound 30 corresponds to one of the groups stated in Table E
' Table 784 Compounds of the general formula I.B (n = 0) in which UR' i8 35 ethylamino, VR" is methoxy, yb is oxygen and Ab for a compound corresponds to one of the groups stated in Table E
Table 785 40 C~,.pGunds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is ethoxy, yb is oxygen and Ab for a c~ ound corresponds to one of the groups stated in Table E
~u~U~4~v~
230 2199~22 Table 786 Co~ ds of the general formula I.B (n = ~) in which UR' is ethylamino, VR" is ethoxy, yb iS oxygen and Ab for a compound 5 corresponds to one of the groups stated in Table E
Table 787 Compounds of the general formula I.B ~n = 0) in which UR' i8 10 methoxy, VRn is methylamino, yb iS oxygen and Ab for a ~ompound corresponds to one of the groups stated in Table E
Table 788 15 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb i8 oxygen and Ab for a co~ ound corresponds to one of the y~Ou~S stated in Table E
Table 789 Co,..~ ds of the general formula I.B (n = 0) in which UR' is methoxy, VR" i8 ethylamino, yb iS oxygen and Ab for a ~ oulld corresponds to one of the groups stated in Table E
25 Table 790 Co~ oul,ds of the general formula I.B (n = 0) in which UR' iB
ethoxy, VRn i8 ethylamino, yb is oxygen and Ab for a c~...~ound corresponds to one of the gL O~S stated in Table E
Table 791 ~ . .
CG~ ndS of the general formula I.B (n 5 O) in which UR' is methoxy, VR" is methoxy, yb is sulfur and Ab for a c~.,.pound 35 corresponds to one of the groups stated in Table E
Table 792 Co...~o~l-ds of the general formula I.B (n = 0) in which UR' is 40 ethoxy, VR" is methoxy, yb i8 sulfur and Ab for a c~...~ou~,d corresponds to one of the groups stated in Table E
.; . . .
Table 793 Cvlllpounds of the general formula I.B (n - 0) in which UR' is methoxy, VR" is ethoxy, yb iS sulfur and Ab for A c~...pound 5 corresponds to one of the groups stated in Table E
Table 794 Cor,.~o~nds of the general formula I.B (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yb is sulfur and Ab for a ~~v...~Gund corresponds to one of the yLUU~s stated in Table E
Table 795 15 CoLIl~oul-ds of the general formula I.B (n = 0) in which UR' is f methylamino, VR" i8 methoxy, yb is sulfur and Ab for a cv.. ,~oul.d corresponds to one of the groups stated in Table E
Table 796 Cu..lpounds of the general formula I.B (n 2 O) in which UR' is ethylamino, VR" is methoxy, yb is sulfur and Ab for a compound corresponds to one of the groups stated in Table E
25 Table 797 C~ unds of the general formula I.B (n = 0) in which UR' i methylamino, VR" is ethoxy, yb is sulfur and Ab for a cor..~our.d corresponds to one of the groups stated in Table E
Table 798 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is sulfur and Ab for a compound 35 corresponds to one of the groups stated in Table E
Table 799 .
Col..pounds of the general formula I.B (n - 0) in which UR' iQ
40 methoxy, VR" i8 methylamino, yb is sulfur and Ab for a co~ ~und corresponds to one of the groups stated in Table E
~050/4~204 ~~ 2I9gL¦~
Table 800 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yb iS sulfur and Ab for a cv,,.~ou,~d 5 corresponds to one of the groups stated in Table E
Table 801 CG..~o~lds of the general formula I.B (n = 0) in which UR' is 10 methoxy, VR" i8 ethylamino, yb is sulfur and Ab for a cv.,,~ound corresponds to one of the ylGU~S stated in Table E
Table 802 15 Compounds of the general formula I.B (n = 0) in which UR' is f ethoxy, VR" is ethylamino, yb iS sulfur and Ab for a compound corresponds to one of the groups stated in Table E
~ 219~f122 Table E
No. Ab 1 3-Fluoropyrid-2-yl 5 2 3-Chloropyrid-2-yl 3 3-Bromopyrid-2-yl 4 3-Methylpyrid-2-yl 3-Trifluoromethylpyrid-2-yl 10 6 3-Metho~y~Lid-2-yl 7 4-Fluo~ id-2-yl 8 4-Chloropyrid-2-yl 9 4-B.~ ~pyLid-2-yl 4-Methylpyrid-2-yl 15 11 4-Trifluoromethylpyrid-2-yl 12 4-Metho~y~yLid-2-yl 13 S-Fluo~pylid-2-yl 14 5-Chloropyrid-2-yl 20 15 5-Bl~ - p~L id-2-yl 16 5-Methylpyrid-2-yl 17 6-Trifluoromethylpyrid-2-yl 18 6-Methoxypyrid-2-yl 25 19 2-F1UOLV~Y L id-3-yl 2-Chlo~opy L id-3-yl 21 2-B,~ -~yrid-3-yl 22 2-Methylpyrid-3-yl 23 2-Trifluoromethylpyrid-3-yl 24 3-Metho~y~ylid-3 (-. 25 4-Fluoropyrid-3-yl 26 4-Chloropyrid-3-yl 27 4-Bromopyrid-3-yl 35 28 4-Methylpyrid-3-yl 29 4-Trifluoromethylpyrid-3-yl 4-Metho~y~yLid-3 31 5-Fluoropyrid-3-yl 40 32 5-Chloropyrid-3-yl 33 5-B.~- ~pyLid-3-yl 34 5-Methylpyrid-3-yl 5-Trifluoromethylpyrid-3-yl 45 36 5-Metho~y~yLid-3 37 6-Fluoropyrid-3-yl 38 Pyrid-2-yl No. Ab 39 Pyrid-3-yl Pyrid-4-yl 5 41 6-Chloropyrid-3-yl 42 6-BLu,.. o~y~id-3-yl 43 6-Methylpyrid-3-yl 44 6-Trifluoromethylpyrid-3-yl 6-Methoxypyrid-3-yl 46 2-Fluoropyrid-4-yl 47 2-ChloLop-yLid-4 48 2-Bromopyrid-4-yl 49 2-Methylpyrid-4-yl 15 50 2-Trifluoromethylpyrid-4-yl ( 51 2-Metho~y~yLid-4 52 3-Fluoropyrid-4-yl 53 3-Chloropyrid-4-yl 20 54 3-Bromopyrid-4-yl 3-Methylpyrid-4-yl 56 3-Trifluoromethylpyrid-4-yl 57 3-Metho~y~y,id-4-yl 4-Fluoropyrimidin-2-yl 59 4-Chloropyrimidin-2-yl 4-BL~ ~pyLimidin-2-yl 61 4-Methylpyrimidin-2-yl 62 4-Trifluoromethylpyrimidin-2-yl 30 63 4-Metho~y~yLimidin-2 64 5-Fluoropyrimidin-2-yl 5-Chloropyrimidin-2-yl 66 5-3romopyrimidin-2-yl 35 67 5-Methylpyrimidin-2-yl 68 5-Trifluoromethylpyrimidin-2-yl 69 5-Metho~y~yLimidin-2-yl 2-Fluoropyrimidin-4-yl 40 71 2-Chloropyrimidin-4-yl 72 2-BL~ ~pyLimidin-4-yl 73 2-Methylpyrimidin-4-yl 74 2-Trifluoromethylpyrimidin-4-yl 2-Trifluoromethylpyrimidin-4-yl 76 2-Metho~y~yLimidin-4 77 5-Fluoropyrimidin-4-yl U~U~4S~4 2199 ~22 No. Ab 78 5-Chloropyrimidin-4-yl 79 5-Bromopyrimidin-4-yl 5 80 5-Methoxypyrimidin-4-yl 81 5-Trifluoromethylpyrimidin-4-yl 82 5-Methoxy~yLimidin-4-yl 83 6-Fluoropyrimidin-4-yl 84 6-Chloropyrimidin-4-yl 6-Bromopyrimidin-4-yl 86 6-Methylpyrimidin-4-yl 87 6-Trifluoromethylpyrimidin-4-yl 88 6-Metho~y~yLimidin-4-yl 15 89 2-Fluoropyrimidin-5-yl ( 90 2-Chloropyrimidin-5-yl 91 2-~romopyrimidin-5-yl 92 2-Methylpyrimidin-5-yl 20 93 2-Trifluoromethylpyrimidin-5-yl 94 2-Methoxypyrimidin-5-yl 4-Fluoropyrimidin-5-yl 96 4-Chloropyrimidin-5-yl 97 4-Bromopyrimidin-5-yl 98 4-Methylpyrimidin-5-yl 99 4-Trifluoromethylpyrimidin-5-yl 100 3-Fluoro-5-trifluoromethylpyrid-2-yl 101 3,6-Dichloro-5-trifluoromethylpyrid-2-yl 30 102 5,6-Dichloro-3-trifluoromethylpyrid-2-yl 103 5-Chloro-3-trifluoromethylpyrid-2-yl 104 3-Chloro-5-trifluoromethylpyrid-2-yl 105 6-Chloro-4-cyanopyrid-2-yl 35 106 3-Cyano-5-nitropyrid-2-yl 107 2-Chloro-6-fluoropyrid-4-yl 108 6-Chloro-4-fluoropyrid-2-yl 109 4,6-Difluoropyrid-2-yl 40 110 3,5-Dichloro-6-fluoropyrid-2-yl 111 6-Methoxy-3-nitropyrid-2-yl 112 4-Cyano-6-fluoropyrid-2-yl 113 6-Chloro-5-cyanopyrid-2-yl 6-Chloro-3-cyanopyrid-2-yl 115 4-Cyano-3,5,6-trifluoropyrid-2-yl 116 6-Chloro-5-nitropyrid-2-yl 21g9~22 No. Ab 117 6-Chloro-3-nitropyrid-2-yl 118 5-Cyano-6-fluoLo~yrid-2 5 119 3-Cyano-6-fluoropyrid-2-yl 120 4,6-Dicyanopyrid-2-yl 121 5-Trichloromethylpyrid-2-yl 122 5-Cyanopyrid-2-yl 123 5-Bromo-4-trifluoromethylpyrid-2-yl 124 3-Nitro-5-trifluoromethylpyrid-2-yl 125 5-Formamidopyrid-2-yl 126 5-Aminopyrid-2-yl 127 2,3,5,6-Tetrafluoropyrid-4-yl 15 128 5-Nitropyrid-2-yl 129 4-methyl-5-nitropyrid-2-yl 130 5-Difluoromethylpyrid-2-yl 131 5-Fluoromethylpyrid-2-yl 20 132 4,6-Difluo~y~imidin-2-yl 133 2,6-Difluoropyrimidin-4-y}
134 2-Chloro-6-trichloromethylpyrimidin-4-yl 135 2,6-Dichloropyrimidin-4-yl 25 136 5-Methoxycarbonylpyrid-2-yl 137 5-Chloro-6-fluoropyrid-2-yl 138 5-Chloro-6-hydL O~y~yL id-2-yl 139 5-Chloro-6-methohy~ylid-2 140 5-Chloro-6-cyanopyrid-2-yl 30 141 5,6-Dichloropyrid-2-yl 142 6-Bromo-5-chloropyrid-2-yl 143 5-Chloro-6-aceto~y~yLid-2 144 S-Bromo-6-fluoropyrid-2-yl 35 145 5-Bromo-6-chloropyrid-2-yl 146 5-Bromo-6-cyanopyrid-2-yl 147 5-Bromo-6-hydro~y~ylid-2-yl 148 5-Bromo-6-metho~y~y~id-2-yl 40 149 5,6-DibL~ y id-2-yl 150 4-Cyanopyrid-2-yl 151 6-Cyanopyrid-2-yl 152 5-Chloropyrid-2-yl 153 4-Chloro-6-methylpyrimidin-2-yl 154 2-Choro-6-f 1UG~ ~~Y ~ id-4-yl 155 5-BL~ - ~ trifluoromethylpyrid-2-yl ~OS0~452U4 ~ 2199 i22 No. Ab 156 4,5-Dichloropyrid-2-yl 157 4,5-Dibromopyrid-2-yl 5 158 5,6-Dichlo~opy~id-2-yl 159 4,6-DichloL O~yL id-2-yl 160 4,6-Dibromopyrid-2-yl 161 5,6-Dibromopyrid-2-yl 162 4-~romo-5-chlolv~y.id-2-yl 163 6-Bromo-5-chloLo~y~id-2-yl 164 5-Bromo-4-chlo~ ~py r id-2-yl 165 5-Bromo-4-chlol ~pyL id-2-yl 166 6-3romo-4-chloropyrid-2-yl 15 167 4-Bromo-6-chloLo~Lid-2-yl r 168 6-Chloro-4-methoxypyrid-2-yl 169 6-~romo-4-metho~y~yLid-2-yl 170 6-Chloroquinazolin-2-yl 20 171 Quinazolin-2-yl 172 5-~enzyloxycarbonylpyridyl 173 4-Formylpyrid-2-yl 174 5-Formylpyrid-2-yl 25 175 6-Formylpyrid-2-yl 176 4-Cyanopyrid-2-yl 177 6-Cyanopyrid-2-yl 178 5-Hydroxymethylpyrid-2-yl 179 6-Chloro-4-trifluoromethylpyrid-2-yl 30 180 6-Chloro-4-trifluoromethylpyrid-2-yl 181 6-Chloro-4-methylpyrid-2-yl 182 2,5-Dichloro-6-cyanopyrid-2-yl 183 2,5-Dichloro-6-carboxypyrid-2-yl 35 184 2,5-Dichloro-6-methoxycarbonyl-pyrid-2-yl 185 4-Cyanopyrid-2-yl 186 6-Trifluoromethylpyrid-2-yl 187 6-Methoxycarbonylpyrid-2-yl 40 188 6-Ca~bo~y~yrid-2-yl 189 4-Pheno~y~yLid-2-yl 190 5-Phenoxy~Lid-2-yl 191 6-Phenoxy~-yrid-2 192 6-Chloropyrid-3-yl 193 4-Phenoxypyrimidin-4-yl 194 4-(4-Methylphenoxy)pyrimidin-4-yl ~0050/~5204 2 1 9 9 ~ 2 2 No. Ab 195 4-Phenoxypyrimidin-2-yl 196 4-(2-Fluorophenoxy)-pyrimidin-2-yl 5 197 4-Phenoxypyrimidin-6-yl 198 4-(4-Chlorophenoxy)pyrimidin-6-yl 199 4-(2-Pyridyloxy)pyrimidin-6-yl 200 4-(6-Chloro-2-pyridyloxy)pyrimidin-6-yl 201 4-(3-Pyridyloxy)pyrimidin-6-yl 202 4-(2-methyl-3-pyridyloxy)pyrimidin-6-yl 203 4-(4-Pyridyloxy)pyrimidin-6-yl 204 2-Furanyl 205 3-Furanyl 15 206 2-Thionyl 207 4-Chloro-2-thienyl 208 5-Chloro-2-thienyl 209 5-Bromo-2-thienyl 20 210 5-Nitro-2-thienyl 211 3-Thienyl 212 2-Chloro-3-thienyl 213 2-Bromo-3-thienyl 25 214 1-Methyl-3-pyrrolyl 215 1-Methyl-2-pyrrolyl 216 1-Benzofuran-2-yl 217 1-Benzofuran-3-yl 218 1-Benzothiophen-2-yl 30 219 1-Benzothiophen-3-yl 220 3-Pyrrolyl 221 2-Pyrrolyl 222 3-Indolyl 35 223 2-Indolyl 224 1-Methyl-3-indolyl 225 1-Methyl-2-indolyl 226 1-Methylpyrazol-4-yl 40 227 1-Methylpyrazol-3-yl 228 Isoxazol-3-yl 229 Isoxazol-4-yl 230 Isoxazol-5-yl 231 Isothiazol-3-yl 232 Isothiazol-4-yl 233 Isothiazol-5-yl ~ ~199~122 No. Ab 234 Oxazol-2-yl 235 Oxazol-5-yl 5 236 Oxazol-4-yl 237 Thiazol-4-yl 238 Thiazol-5-yl 239 Thiazol-2-yl 240 1-Methylimidazol-4-yl 241 1-Methylimidazol-5-yl 242 1-Methylimidazol-2-yl 243 1,2-Benzisoxazol-3-yl 244 1,2-Benzisothiazol-3-yl 15 24S l-Methylindazol-3-yl 246 Benzoxazol-2-yl 247 5-Chlorobenzoxazol-2-yl 248 6-Fluorobenzoxazol-2-yl 20 249 Benzothiazol-2-yl 250 5-Fluorobenzothiazol-2-yl 251 6-Fluorobenzothiazol-2-yl 252 Pyrido[3,2-d]thiazol-2-yl 25 253 (6-Chloro-pyrido)[3,2-d]thiazol-2-yl 254 1-Methyl-1,2,3-triazol-5-yl 255 1-Methyl-1,2,3-triazol-4-yl 256 1-Methyl-1,2,4-triazol-5-yl 257 1-Methyl-1,2,4-triazol-3-yl 30 258 1-Methyl-1,2,3,4-tetrazol-5-yl 259 2-Methyl-1,2,3,4-tetrazol-5-yl 260 5-Trifluoromethyl-1,3,4-thiadiazol-2-yl 261 6-Chlorobenzoxazol-2-yl 35 262 5-Fluorobenzoxazol-2-yl 263 5-Nitrothiazol-2-yl Table 803 40 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab i5 phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
~ 2199 122 Table 804 Cv~ uu~.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl 5 radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each c~,..pou~ld to a line of Table F
Table 805 Compounds of the general formula I.B (n = 0) in which UR' i8 methoxy, VR" is ethoxy, yb is oxygen and Ab i8 phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for 15 each compound to a line of Table F
Table 806 C~.l.pounds of the general formula I.~ (n = 0) in which UR' is 20 ethoxy, VR" is ethoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the comh;nation of the index o and of the R~ group corresponding for each compound to a line of Table F
25 Table 807 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the 30 combination of the index o and o~ the R~ group corresponding for each compound to a line of Table F
Table 808 35 CG~ ounds of the general formula I.B (n ~ 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each co.,.po~..d to a line of Table F
Table 809 Co~ ounds of the general formula I.B tn = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab i~ phenyl, this 45 phenyl radical carrying an -Oo~R~ group in the 3 position and the ~ 2199~22 combination of the index o and of the R~ group corresponding for each col"~o~nd to a line of Table F
Table 810 Compounds of the general formula I.3 (n = 0) in which UR' is ethylamino, VR~' is ethoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for 10 each com~urld to a line of Table F
Table 811 Compounds of the general formula I.B (n 3 O) in which UR' is 15 methoxy, VR" is methylamino, yb is oxygen and Ab i8 phenyl, this f phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table 812 C~...pounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is phenyl, this phenyl radical carrying an -Oo~R~ group in the 3 position and the 25 comh;n~tion of the index o and of the R~ group corresponding for each co..~Gulld to a line of Table F
Table 813 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb is oxygen and Ab is phenyl, this ' phenyl radical carrying an -Oo~R~ gro~p in the 3 position and the comh; n~tion of the index o and of the R~ group corre~ponding for each compound to a line of Table F
Table ôl4 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb i8 oxygen and Ab is phenyl, this 40 phenyl radical carrying an -Oo~R~ group in the 3 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
0050/452~4 2~9gl22 Table 815 CG~ ounds of the general formula I.B (n = 0) in which UR ' is methoxy, ~R" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 5 2-pyridyl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 816 C~l..p~unds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the co~hl n~tion of the index o and of the R~ group corresponding 15 for each cv...~u,,d to a line of Table F
( Table 817 Compounds of the general formula I.B ~n = 0) in which UR ' is 20 methoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each ~~vI..~ound to a line of Table F
25 Table 818 CG...~oullds of the general formula I.B (n = 0) in which UR ' is ethoxy, VR~' is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and 30 the combination of the index o and of the R~ group corresponding for each cv~ ound to a line of Table F
Table 819 35 CG.n~Gunds of the general formula I.B (n 8 O) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the co~h~n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 820 Compounds of the general formula I.3 (n = 0) in which UR' is ethylamino, VR is methoxy, yb is oxygen and Ab is 2-pyridyl, this 45 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and 2~994~2 the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 821 Co~..po~lds of the general formula I.~ (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding 10 for each compound to a line of Table F
Table ô22 Compounds of the general formula I.B (n = 0) in which UR ' is 15 ethylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this ( 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table ô23 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position 25 and the combination of the index o and of the R~ group corresponding for each cv,..~ou,ld to a line of Table F
Table 824 30 Compounds of the general formula I.B (n = 0) in which UR ' is ethoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 825 Compounds of the general formula I.B (n = 0) in which UR ' is methoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 40 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the comh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
~ 2199~22 Table 826 Co~ o~llds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 5 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 827 C~ oui~ds of the general formula I.B (n - 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 15 for each ~oh.pGund to a line of Table F
Table 828 Compounds of the general formula I.B (n = 0) in which UR' is 20 ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each cv~ o~nd to a line of Table F
25 Table 829 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an - Oo~R~ group in the 4 position and 30 the combination of the index o and of the R~ group corresponding - for each c. Eound to a line of Table F
. .
Table 830 35 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an - Oo~R~ group in the 4 position and the c~mh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 831 Compounds of the general formula I.B (n = o) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, 45 this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position ~ == = -.
and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 832 CG.,.~o~nds of the general formula I.B ~n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 10 for each ~ pound to a line of Table F
Table 833 Co,..pounds of the general formula I.B (n 3 O) in which UR' i~
15 methylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each ~v...~ur.d to a line of Table F
20 Table 834 Co,..~ounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and 25 the combination of the index o and of the R~ group corresponding for each c~ ~ulld to a line of Table F
Table ô35 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 836 Compounds of the general formula I.~ (n = 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is 2-pyridyl, this 40 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each co...po~l-d to a line of Table F
.
0050/4~Z04 -246 2 1 9 g 4 2 2 Table 837 C~,~.~ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb i8 oxygen and Ab i8 2-pyridyl, this 5 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of ~able F
Table 838 C~..poul,ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding 15 for each co.,.~o~,ld to a line of Table F
Table 839 Compounds of the general formula I.B (n - 0) in which UR' is 20 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each cv,~o~nd to a line of Table F
25 Table 840 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 30 position and the combination of the index o and of the R~ group - corresponding for each compound to a line of Table F
Table 841 35 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 842 Co.,.~Gu..ds of the general formula I.B (n s 0) in which UR ' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 45 pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 843 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of 10 the R~ group corresponding for each compound to a line of Table F
Table 844 Compounds of the general formula I.B (n = 0) in which UR' is 15 ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
20 Table 845 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR is ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 25 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 846 30 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, ' this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 847 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VRn is methylamino, yb is oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~ ulld to a line of Table F
248 2I99~22 Table 848 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methylamino, yb i5 oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 849 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group 15 corresponding for each compound to a line of Table F
Table 850 Compounds of the general formula I.B (n = 0) in which UR' is 20 ethoxy, VRn is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the comhinAtion of the index o and of the R~ group corresponding for each cv...~o~nd to a line of Table F
25 Table 851 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and 30 the combination of the index o and of the R~ group corresponding for each co,.,~ound to a line of Table F
Table 852 35 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in th~ 6 position and the combination of the index o and of the R~ group corresponding for each ov...~o~nd to a line of Table F
Table 853 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb iS oxygen and Ab is 2-pyrazinyl, this 45 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and .
~ 2I99ll22 the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 854 CG.,.~ounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i3 ethoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ ~roup corresponding lO for each ~vm~o~nd to a line of Table F
Table 855 Compounds of the general formula I.B ~n = 0) in which UR' is 15 methylamino, VR" is methoxy, yb is oxygen and Ab i8 2-pyrazinyl, f~ this 2-pyraz~nyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ~und to a line of Table F
20 Table 856 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb i8 oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 25 position and the combination of the index o and of the R~ group corresponding for ea~h cv.l.pound to a line of Table F
Table 857 30 Compounds of the general formula I.B (n = 0) in which UR' is ;- methylamino, VR i8 ethoxy, yb is oxygen and Ab i8 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 858 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR is ethoxy, yb is oxygen and Ab is 2-pyrazinyl, 40 this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the com~nation of the index o and of the R~ group corresponding for each compound to a line of Table F
-0050~45204 Table 859 Co~ unds of the general formula I.B (n = 0) in which UR' is methoxy, VR" i5 methylamino, yb is oxygen and Ab is 2-pyrazinyl, 5 this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 860 Co.~.~Gunds of the general formula I.B (n = 0) in which UR' i8 ethoxy, VRn is methylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group lS corresponding for each compound to a line of Table F
,f Table 861 C~ _u,lds of the general formula I.B (n - 0) in which UR' is 20 methoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination.of the index o and of the R~ group corresponding for each compound to a line of Table F
25 Table 862 Compounds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 30 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
2199~22 Table F
No. o R~
o COCH3 6 0 CH=NOCH3 7 0 C~CH3)-NOCH3 8 0. COOH
15 11 0 3-Cl-CcH~
12 0 3-CN-C6H~
20 lS 0 3-CH3O-C6H4 18 1 2-Cl-C6H4 25 19 1 2-Br-C6H~
1 2-CN-C6H~
21 1 2-NO2-C6H~
22 1 2-CF3-C6H~
23 1 2-CH3-C6H~
1 2-n-C3H7-C6H4 31 1 2-CH=NOCH3-C6H4 40 32 1 2-C(CH3)=NOCH3-C6H4 37 1 2-CONH2-C6H~
38 1 2-CSNH2-C6H~
2199~22 No. o R~
5 41 1 2-CH3C00-C6Hg 42 1 2-CH3C00-C6H~
51 1 2-CH3S02NH-C6H~
52 1 2-CH3S02NH-C6H~
53 1 2,6-Difluorophenyl 20 54 1 2,6-Difluorophenyl 1 2,6-Difluorophenyl 56 1 3,6-Difluorophenyl 57 1 3,6-Difluorophenyl 1 . 3,6-Difluorophenyl 59 1 3-Cl-pyrid-2-yl 1 3-Cl-pyrid-2-yl 61 1 3-Cl-pyrid-2-yl 62 1 3-CN-pyrid-2-yl 30 63 1 3-CN-pyrid-2-yl ( 64 1 3-CN-pyrid-2-yl 1 3-CH3-pyrid-2-yl 66 1 3-CH3-pyrid-2-yl 35 67 1 3-CH3-pyrid-2-yl 68 1 3-CH30-pyrid-2-yl 69 1 3-CH30-pyrid-2-yl 1 3-CH30-pyrid-2-yl 40 71 1 3-CSNH2-pyrid-2-yl 72 1 3-CSNH2-pyrid-2-yl 73 1 3-CSNH2-pyrid-2-yl 74 1 4-F-pyrid-3-yl 4 75 1 4-F-pyrid-3-yl 76 1 4-F-pyrid-3-yl 77 1 4-CN-pyrid-3-yl .
_ 2193~22 No. o R~
78 1 4-CN-pyrid-3-yl 79 1 4-CN-pyrid-3-yl 5 80 1 4-CH3-pyrid-3-yl 81 1 4-CH3-pyrid-3-yl 82 1 4-CH3-pyrid-3-yl 83 1 Pyrimidin-2-yl 84 1 Pyrimidin-2-yl 1 Pyrimidin-2-yl 86 1 2-CH3-pyrimidin-2-yl 87 1 2-CH3-pyrimidin-2-yl 88 1 2-CH3-pyrimidin-2-yl 92 0 Br 20 93 o CH3 gS 0 pyrid-2-yl 96 0 Pyrimidin-2-yl (CH3)3 100 1 n-C3H7 101 1 i-C3H7 30 102 1 pyrid-2-yl ( 103 1 1-pyrid-3-yl 104 1 2-F-pyrid-3-yl 105 1 2-Cl-pyrid-3-yl 35 106 1 2-CN-pyrid-3-yl 107 1 2-CH3-pyrid-3-yl 108 l 2-CH30-pyrid-3-yl 109 1 2-CSNH2-pyrid-3-yl 2199 1~2 Table 863 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each ~ ound to a line of Table G
Table 864 Cv..*vunds of the general formula I.B (n - 0) in which UR' i~
ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 15 corresponding for each cv...~ound to a line of Table G
Table 865 Co.~oullds of the general formula I.B (n = 0) in which UR ' is 20 methoxy, VR" i8 ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each co...~ou~d to a line of Table G
25 Table 866 Compounds of the general foL ~ I.B (n - 0) in which UR ' i8 ethoxy, VR" is ethoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position 30 and the combination of the index o and of the R~ group ( correspon~; ng for each col,.pou~.d to a line of Table G
Table 867 35 Compounds of the general formula I.B (n = o) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the combination of thè index o and of the R~ group corresponding for each compound to a line of Table G
Table 868 Compounds of the general formula I.B (n = o) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 45 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 869 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 10 corresponding for each c~ o~nd to a line of Table G
Table 870 Compounds of the general formula I.B (n = 0) in which UR' is 15 ethylamino, VR" is ethoxy, yb i5 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~",~o~nd to a line of Table G
20 Table 871 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR is methylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~
25 group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ou,.d to a line of ~able G
Table 872 30 Co.llpo~llds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is methylamino, yb i8 oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each cv...pound to a line of Table G
Table 873 C~ ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR is ethylamino, yb iS oxygen and Ab is pyrimidin-4-yl, 40 this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
OOSOt45204 2I9~'122 Table 874 Co..~oul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 875 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" .is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each compound to a line of Table G
f Table 876 Compounds of the general ~ormula I.B (n - 0) in which UR' is 20 ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
25 Table 877 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb i8 oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 30 position and the com~ination of the index o and of the R~ group - corresponding for each compound to a line of Table G
Table 878 35 C~ -ul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the co~bination of the index o and of the R~ group corresponding for each c~,llpG~nd to a line of Table G
Table ô79 CGll*o~nds of the general formula I.B (n - 0) in which UR' is methylamino, VR" i8 methoxy, yb is oxygen and Ab is 45 pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
~ 257 2199~22 group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 880 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 10 corresponding for each . 3und to a line of Table G
Table 881 Co,.,~ounds of the general formula I.B (n = 0) in which UR ' is 15 methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, ( this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each ~v...~ound to a line of Table G
20 Table 882 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 25 position and the combinat~on of the index o and of the R~ group corresponding for each ~ ~u,.d to a line of Table G
Table 883 30 Co...~ounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
group in the 4 position and the combination of the index o and of the R~ group corresponding for each col..yG~nd to a line of Table G
Table 884 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn is methylamino, yb i5 oxygen and Ab is pyrimidin-2-yl, 40 this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
~9!3422 Table 885 Compounds of the general formula I.B (n = 0) in which UR ' is methoxy, VR" i5 ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, 5 this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 886 Compounds of the general formula I.B (n G o) in which UR ' is ethoxy, VR" i9 ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each ~-vl~.~ound to a line of Table G
( Table ô87 Compounds of the general formula I.B (n - 0) in which UR ' is 20 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each co~ Gund to a line of Table G
25 Table 888 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, thi~ pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 30 position and the combination of the index o and of the R~ group corresponding for each cv...~ound to a line of Table G
Table 889 3S Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is ethoxy, yb i8 oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~ ound to a line of Table G
Table 890 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR~' is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 45 pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position ~ 259 2199~22 and the combination of the index o and of the R~ group correspo~;ng for each co...po~lld to a line of Table G
Table 891 s Co...~ounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of 10 the R~ group corresponding for each c~ ou.ld to a line of Table G
Table 892 Compounds of the general formula I.B (n = 0) in which UR' i~
f 15 ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
20 Table 893 Cur..p~nds of the general formula I.B (n 5 O) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 25 position and the combination of the index o and of the R~ group corresponding for each cG..,~ound to a line of Table G
~able 894 30 Compounds of the general formula I.B (n = 0) in which UR' is ethylam. ino~ VR" is ethoxy, ~b is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an - Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 895 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methylamino, yb is oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the c~mh;n~tion of the index o and of the R~ group corresponding for each con.pou,ld to a line of Table G
0050/45~04 2199~22 Table 896 Co...~ ds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yb is oxygen and Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and o~ the R~ group correspon~;ng for each compound to a line of Table G
Table 897 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VRn iS ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group 15 corresponding for each ~l"~ound to a line of Table G
Table 898 Compounds of the general formula I.B (n a O) in which UR' is 20 ethoxy, ~R" i8 ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~ group in the 2 position and the combination of the index o and of the R~ group corresponding for each ~..,po~nd to a line of Table G
25 Table G
No. o R~
2 0 Cl 30 3 0 Br 9 0 CH=NOCH3 0 C(CH3)=NOCH3 13 0 C6Hs 0 3--Cl--C6H4 17 0 3-CH3-C6H~
, ~ 261 2199~22 No. o R~
5 20 0 C6H5-CH(OH) 23 ~ C2H5 24 0 n-C3H7 0 i-C3H7 27 0 Pyrimidin-2-yl 28 0 5-CH3-pyrimidin-2-yl 15 29 0 C(CH3)3 0 Pyrimidin-2-yl Table 899 C~ ou~lds of the general formula I.B (n = O) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab i8 pyrimidin-4-yl, 25 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each ~ und to the substituents stated in a line of Table H
Table 900 Compounds of the general formula I.B (n - O) in which UR' i8 ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each 35 c~ Gu,ld to the substituents stated in a line of Table H
Table 901 Compounds of the general formula I.B (n = O) in which UR' is 40 methoxy, VR~ is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each cGr..~l~d to the substituents stated in a line of Table H
219~2~
Table 902 Cv,,,~unds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 5 pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 903 Cor.,~ounds of the general formula I.B (n 5 O) in which UR' is methylamino,.VR" is methoxy, yb is oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 1~ corresponding for each ~..~ound to the substituents stated in a ( line of Table H
Table 904 20 C~..-~Gunds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each co~ ou.ld to the substituents stated in a line of Table H
Table 905 Co~ ou~lds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidln-4-yl, 30 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy ( group in the 6 position and the R~ group corresponding for each c~ oulld to the substituents stated in a line of Table H
Table 906 Co~ Gu-lds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb iS oxygen and Ab is~ pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group correspondlng for each 40 cv..*~und to the substituents stated in a line of Table H
Table 907 Compounds of the general formula I.~ (n = 0) in which UR' is 45 methoxy, VR" is methylamino, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 0050/45~04 corresponding for each compound to the substituents stated in a line of Table H
Table 908 Co".~ul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn i8 methylamino, yb is oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each 10 ~ und to the substituents stated in a line of Table H
Table 909 Compounds of the general formula I.B (n = 0) in which UR' is 15 methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each co...~ound to the substituents stated in a line of Table H
20 Table 910 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy 25 group in the 6 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 911 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each c~.~.~ound to the substituents stated in a line of Table H
Table 912 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 40 this pyri~idin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 913 Compounds of the general formula I.B (n = 0) in which UR' i5 methoxy, VR" is ethoxy, yb iS oxygen ~nd Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 914 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is etho~y, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each co,..p~ulld to 15 the substituents stated in a line of Table H
Table 915 Compounds of the general formula I.B (n = 0) in which UR' is 20 methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 916 C~...po~nds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 30 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each cv.~.pound to the substituents stated in a line of Table H
Table 917 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is~pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each 40 col"~ound to the substituents stated in a line of Table H
Table 918 Compounds of the general formula I.B (n = o) in which UR' is 45 ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy OOS0/45~04 2~9g~22 group in the 2 position and the R~ group corresponding for each co.,.~o~nd to the substituents stated in a line of Table H
Table 919 Co".~ounds of the general formula I.B (n - 0) in which UR' is methoxy, VR is methylamino, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group 10 corresponding for each cvA..~ou,~d to the substituents stated in a line of Table H
Table 920 15 Compounds of the general formula I.B (n = 0) in which UR' is ( ethoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 921 Compounds of the general formula I.B (n = 0) in which UR' i~
methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, 25 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each cv~,lpuund to the substituents stated in a line of Table H
Table 922 ,- Co~ oullds of the general formula I.B (n = 0) in which UR~ is ethoxy, VR" i8 ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each 35 compound to the substituents stated in a line of Table H
Table 923 Compounds of the general formula I.B (n = 0) in which UR' is 40 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
4~
~199~22 Table 924 Compounds of the general formula I.B (n = 0) in which UR' i5 ethoxy, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, S this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 925 C~."~o~nds of the general formula I.B (n = 0) in which UR' is methoxy, VR" .i5 ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 15 c _und to the substituents stated in a line of Table H
f ~- Table 926 Co~ oucds of the general formula I.B (n - 0) in which UR' is 20 ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
25 Table 927 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an 30 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a { line of Table H
Table 928 Co~ unds of the general formula I.B (n = o) in which UR' is ethylamino, VR~ is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 40 co~ nd to the substituents stated in a line of Table H
Table 929 Compounds of the general formula I.B (n = 0) in which UR' is 45 methylamino, VRn is ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy 267 2 1 9 ~ll2 2 group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 930 CGl.,pounds of the general formula I.B (n = 0) in which UR' is ethylamino, VRn is ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 10 compound to the substituents stated in a line of Table H
Table 931 Compounds of the general formula I.B (n = 0) in which UR' is 15 methoxy, VRn is methylamino, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each c~l..pGulld to the substituents stated in a line of Table H
Table 932 CGr..~G~nds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-2-yl, 25 this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each co..~Gund to the substituents stated in a line of Table H
Table 933 C~...po~,.ds of the general formula I.B (n - 0) in which UR' i8 methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 35 co.,.pou..d to the substituents stated in a line of Table H
Table 934 CGl..pounds of the general formula I.B (n - 0) in which UR' is 40 ethoxy, VRn is ethylamino, yb i8 oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
2199~2 Table 935 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb iS oxygen and Ab i8 5 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group C~l esponding ~or each ~ .~ound to the substituents stated in a line of Table H
10 Table 936 Cv...~nds of the general formula I.B (n ~ 0) in which UR' is ethoxy, VR" is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy 15 group in the 4 position and the R~ group corresponding for each c~"lpoul~d to the substituents stated in a line of Table H
Table 937 20 C~.,*ounds of the general formula I.~ (n = 0) in which UR' is methoxy, VR" is ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 938 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, 30 this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each f compound to the substituents stated in a line of Table H
Table 939 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 40 corresponding for each cr Eound to the substituents stated in a line of Table H
Table 940 45 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an u~ u~
~ 269 2199~22 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line o~ Table H
5 Table 941 co"l~vu-ds of the general formula I.B (n ~ 0) in which UR' is methylamino, VR" is ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an 10 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each ~ ou.ld to the substituents stated in a line of Table H
Table 942 C Compounds of the general form~ I.B (n 2 o~ in which UR' is ethylamino, VRn is ethoxy, yb i8 oxygen and ~b i8 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 20 corresponding for each ~u..l~ou.,d to the substituents stated in a line of Table H
Table 943 25 Compounds of the general for~ (n = 0) in which UR' is methoxy, VR" is methylamino, yb i8 oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each c~."~ourld to the substituents stated in a 30 line of Table H
f Table 944 Compounds of the general formula I.B (n = 0) in which UR' is 35 ethoxy, VR" is methylamino, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substitue~ts stated in a line of Table H
Table 945 Compounds of the general formula I.~ (n = 0) in which UR' is methoxy, VR" is ethylamino, yb iS oxygen and Ab is 45 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 2~99~2 corresponding for each compound to the substituents stated in a line of Table H
Table 946 Compounds of the general formula I.B (n 2 0) in which ~R' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 10 corresponding for each c~...po~nd to the substituents stated in a line of Table H
Table H
15 No. R~
3 2-Cl 4 3-Cl 2-Br 6 2-Cyano 7 3-Cyano 8 2-Isocyano 12 3-NH(CH3) 30 13 2-N(CH3)2 18 3-NH-CONH(C2Hs) 19 2-NH-SocH3 45 26 2-(2-F-C6H4O) ~U~/4~4 ~ 271 2199'122 No. R~
29 3-(4-CH3-C6S020) 34 2-S(O)CH3 39 3-COC6Hs 15 40 2-(E)-CH'NOH
( 41 3-(E)-CH=NOH
42 2-(E)-CH5NOCH3 43 2-(E)-C(CH3)=NOH
3-CONH(CH3) 47 2-CSNH(CH3) 3-C2Hs 52 2-CH2Br 30 53 2-CH2Cl f 54 2-CH2CN
40 61 2-CH=CH2 62 2-CH2-CH=CH2 63 2-C_CH
64 2-CH2_CH
3-CH2C(CH3)=CH2 2-OCH2CH=CH2 67 3-OCH2CH=CH2 ~ 2199~22 No. R~
69 3-c6H5 5 70 2-C6HsO
72 2-(4-Cl-C6H40) 74 2-OCH3, 3-OCH3 2-Cyano, 5-Cl 76 2-Cyano, 6-Cyano 77 2-F, 5-Cl 78 3-OCH3, 5-OCH3 15 79 2-No2, 3-OCH3 3-oCH2, 5-Cyano 84 2-i-C3H7 2-i-C3H70 86 2-F, 6-F
2-F, 3-F
88 2-n-C3Hp 89 2-n-C~HgO
2-CH(OH)CH3 91 2~t~CqHg 30 92 2-s-C4Hg r g3 2-n-C3H7 94 2-(E/Z)-CH=CH(CH3) 2-Cyano, 5-OCH3 35 96 2-Cyano, 5-N(C2Hs) 2 97 ~ 2-CONH2 98 2-C_CSi(CH3)3 99 2-F, 5-F
40 100 2-(E)-CH300C-C-CHOCH3 101 3-F, 5-F
106 2-Cyano, 6-F
~U50/452~4 ~ 219~'122 No. R~
107 2-NO2, 6-F
108 2-CSNH2, 6-F
S 109 2-Cyano, 3-F
110 2-Cyano, 5-F
111 2-Cyano, 3-OCH3 112 2-Cyano, 6-OCH3 113 2-NO2, 5-OCH3 114 2-NO2, 6-OCH3 115 2-CSNH2, 3-OCH3 116 2-CSNH2, 5-OCH3 117. 2-CSNH2, 6-OCH3 15 118 2-Cyano, 3-Cyano 119 2-F, 3-Cyano 120 .2-OCH3, 3-Cyano 121 3-Cyano, 6-F
20 122 2-Cyano, 6-Br 123 2-Cyano, 6-NO2 124 2-Cyano, 6-OC2Hs 125 2-Cyano, 6-CO2C2H5 25 126 2-Cyano, 6-CH3 127 2-Cyano, 5-CH2C6H5 129 2-C(CH3)=NOCH3 ~' 132 4-oc6H5 133 4-Cyano 35 135 4-(E)-CH=NOH
136 4-(E)-CH=NOCH3 137 4-(E)-C(CH3)=NOCH3 140 4-SO2(CH2)3CH3 142 2-F, 4-F
143 2-Cl, 4-Cl 144 2-NO2, 4-F
145 2-CN, 4-Cl ., 0050/45204 2 1 9 9 ~ 2 2 No. R~
146 2-CN, 4-Br 147 2-CN, 4-NO2 5 148 2-CN, 4-OCH3 149 2-CN, 4-OCF3 150 2-CN, 4-CN
151 2-CN, 4-COOCH3 152 3-CN, 4-F
153 2-CSNH2, 4-OCH3 154 2-NO2, 4-OCH3 Table 947 Co,..~o~llds of the general formula I.C (n - 0) in which UR' is methoxy, V-R" i8 methoxy, yc i8 CH=C(Cl)-C(=O)-O-# (-~ = bond to AC) and Ac for a cv,..~ou..d corresponds to a group of Table I.1 20 Table 948 C~ ou,lds of the general formula I.C (n = 0) in which UR' i~
ethoxy, VR" is methoxy, yc i~ CH=C(Cl)-C(=O)-O-# (-# = bond to AC) and Ac for a cvl..~oul.d corresponds to a group of Table I.l Table 949 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to AC) 30 and Ac for a compound corresponds to a group of Table I.l f Table 950 Compounds of the general formula I.C (n - 0) in which UR' i9 35 ethoxy, VR" is ethoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to Ae) and Ac for a compound corresponds to a group of Table I.l Table 951 40 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to AC) and Ac for a cG,.,~ound corresponds to a group of Table I.1 U~5~
Table 952 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VRn is methoxy, yc is CH=C(Cl)-C(=0)-0-# (-~ = bond to 5 AC) and Ac for a c~ ound corresponds to a group of Table I.1 Table 953 CG...~uunds of the general formula I.C (n = 0) in which UR' i8 10 methylamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-o-# (-~ = bond to AC) and Ac for a cv...pou~ld corresponds to a group of Table I.l Table 954 15 Co...~uu--ds of the general formula I.C (n = 0) in which UR' is < ethylamino, VR" is ethoxy, yc is CH=C(C1)-C(=0)-0-# (-~ = bond to AC) and Ac for a co...~u~.d corresponds to a group of Table I.l Table 955 Cv...pounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH=c(cl)-c(=o)-o-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.l 25 Table 956 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methylamino, yc i8 CH=C(Cl)-C(=0)-0-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.l Table 957 C~...~ou..ds of the general formula I.C (n ~ 0) in which UR' is methoxy, VR is ethyla~ino, yc is CH=C(Cl)-C(=0)-0-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.1 Table 958 Compounds of the general formula I.C (n = 0) ~n which UR' is 40 ethoxy, VRn is ethylamino, yc is CH=C(Cl)-C(=0)-0-# t-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.l ~ 2199~22 Table 959 Cor,.A~o~Ads of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH~C~A~r)-C(-0)-O-~ (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 960 Cu...po~Ands of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" i8 methoxy, YQ i8 CH=C(A~r) - C(=o)-O-# (-# = bond to AC) and Ac for a compound co~responds to a group of Table I.1 Table 961 15 C~A.~ounds of the general formula I.C (n = 0) in which UR' is ~ methoxy, VR" i8 ethoxy, yc is CH=C(Br)-C(=O)-O-# (-~ = bond to AC) and Ac for a ~o...A~ound corresponds to a group of Table I.1 Table 962 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is ethoxy, yc is CH=C(Br)-C(=O)-O-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.1 25 Table 963 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(A~r)-C(=0)-O-# (-# = bond to AC) and Ac for a cG,.,A~ou.,d corresponds to a group of Table I.l Table 964 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C(Br)-C(=O)-O-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.1 Table 965 ~
Compounds of the general formula I.C (n = 0) in which UR' is 40 methylamino, VR" is ethoxy, yc is CH=C(A~r)-C(=O)-O-# (-# e bond to AC) and Ac for a cv~A..ApouA.d corresponds to a group of Table I.l ~S~/4~4 ~ 277 ~I99~22 Table 966 Co~ uullds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc is CH=C(Br)-C(=0)-O-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 967 Cu.-.~o~,,ds of the general formula I.C (n - 0) in which UR' is 10 methoxy, VRn is methylamino, yc is CH=C(Br)-C(=0)-O-# (-# = bond to AC) and Ac for a co,-,~nd corresponds to a group of Table I
Table 968 15 Compounds of the general formula I.C (n = O) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(Br)-C(=O)-O-# (-# = bond to AC) and Ac for a ~m~o~nd corresponds to a group of Table I.l Table 969 Compounds,of the general formula I.C (n - 0) in which UR' is methoxy, VR" i8 ethylamino, yc i8 CH=C(Br)-C(=0)-O-# (-# = bond to AC) and Ac for a ~v."poulld corresponds to a group of Table I.l 25 Table 970 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=c(Br)-c(=o)-o-# (-# 2 bond to AC) and Ac for a ~r..poulld corresponds to a group of Table I.l Table 971 ~.--Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-~ (-# - bond to AC) 35 and Ac for a c~ o~nd corresponds to a group of Table I.l Table 972 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR is methoxy, yc is CH=c(cN)-c(-o)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.1 278 2~99~22 Table 973 Compounds of the general formula I.C (n s 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(CN)-C(=0~-# (-# = bond to AC) S and Ac for a compound corresponds to a group of Table I.1 Table 974 Cv~ Gunds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yc i~ CH=C(CN)-C(=O)-~ = bond to AC) and Ac for a compound corresponds to a group of Table I..1 Table 975 lS Compounds of the general formula I.C (n - 0) in which UR' is methoxy, VR" i8 methoxy, yc is CH=c(cN)-c(~o)-o-# (-# = bond to AC) and Ac for a ~ ol-nd corresponds to a group of Table I.1 Table 976 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methoxy, Y~ i8 CH=C(CN)-C(=0)-0-# (-# = bond to AC) and Ac for a c~m~nd corresponds to a group of Table I.1 25 Table 977 Compounds of the general formula I.C (n = 0) in which UR' i~
methoxy, VR is ethoxy, yc is CH=C(CN)-C(=O)-O-# (-~ = bond to AC) and Ac for a cG".~oulld corresponds to a group of Table I.l r Table 978 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(CN)-C~=O)-O-# (-# = bond to AC) 35 and Ac for a compound corresponds to a group of Table I.l Table 979 Compounds of the general formula I.C (n = 0) in which UR' is 40 methylamino, VRn is methoxy, yc is CH=C(CN)-C(=O)-O-# (-# = bond to AC) and Ac for a cvl..pound corresponds to a group of Table I.l 0050/4~204 Table 980 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=c(cN)-c(=o)-o-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 981 Compounds of the general formula I.C (n = 0) in which UR' is 10 methylamino, VR" is ethoxy, yc is CH=C(CN)-C(sO)-0-# (-# = bond to AC) and Ac for a c~ po~nd corresponds to a group of Table I.1 Table 982 lS Compounds of the general formula I.C (n = 0) in which UR' i8 ethylamino, VRn is ethoxy, yc is CH=C(CN)-C~=0)-0-# (-~ 3 bond to ~~ AC) and Ac for a compound correspond~ to a group of Table I.l Table 983 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH=C(CN)-C(=0)-0-~ (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I
25 Table 984 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(CN)-C(=O)-O-# (-# = bond to AC) and Ac for a co,~nd corresponds to a group of Table I.l f Table 985 . .
Compounds of the general formula I.C (n - 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-O-~ (-# = bond to 35 AC) and Ac for a cor.pound corresponds to a group of Table I.l Table 986 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR" i8 ethylamino, yc i8 CH=C(CN)-C(=o)-0-# (-# - bond to AC) and Ac for a oo~ o~nd corresponds to a group of Table I.
0050~45204 ' ~ . 280 2199422 Table 987 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc i8 CH=C(N02)-C(=O)-O-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 988 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VRn is methoxy, yc is CH=C(N02)-C(=0)-0-# (-~ = bond to AC) and Ac for a cv~ und corresponds to a group of Table I.1 Table 989 15 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethoxy, yc is CHsC(N02)-C(cO)-0-# (-~ = bond to '- AC) and Ac for a compound corresponds to a group of Table I.l Table 990 Co,ll~o~nds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-~ - bond to AC) and Ac for a corll~oul~d corresponds to a group of Table I.1 25 Table 991 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" i8 methoxy, yc is CH=C(N02)-C(=o)-o-# (-# = bond to AC) and Ac for a co~ Gund corresponds to a group of Table I.l Table 992 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, Y~ is CH=C(N02)-C(=O)-O-# (-# = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.l Table 993 Compounds of the general formula I.C (n c 0) in which UR' is 40 methylamino, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-# = bond to AC) and Ac for a c~..*o~nd corresponds to a group of Table I.l ~ 281 219~122 Table 994 CG~ oul.ds of the general formula I.C (n = 0) in which UR' i8 ethylamino, VR" is ethoxy, yc i8 CH=C(N02)-C(=O)-O-# t-* = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 995 Co...~ounds of the general formula I.C (n = 0) in which UR' is 10 methoxy, VR" is methylamino, YC is CH=C(N02)-C('O)-O-# (-~ = bond to AC) and Ac for a ~v..~ound corresponds to a group of Table I.1 Table 996 15 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(N02)-C(-0)-0-# (-# = bond to AC) and Ac for a co,.,~oul,d corresponds to a group of Table I.l Table 997 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc i8 CH=C(N02)-C(=O) - o_# (-# e bond to AC) and Ac for a co.~.~ound corresponds to a group of Table I.l 25 Table 998 Co...~oul,ds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(N02)-C(-0)-0-~ 3 bond to AC) and Aa for a ~-v,ll~Gund corresponds to a group of Table I.l r Table 999 Co,ll~o~.,ds of the general formula I.C (n = 0) in which UR' is methoxy, VR~ is methoxy, yc is CH=C(Cl)-C(=0)-NH-~ (-# = bond to ~5 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1000 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR" i8 methoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# - bond to AC) and Ac for a co~ ound corresponds to a group of Table I.2 282 ~199~22 Table 1001 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR~ i8 ethoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to 5 AC) and Aa for a compound corresponds to a group of Table I.2 Table 1002 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I..2 Table 1003 15 Cv.,,pvunds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a cv",~o~-ld corresponds to a group of Table I.2 Table 1004 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=c(cl)-c(=v)-NH-# (-# = bond to AC) and Ac for a cv.,,po~nd corresponds to a group of Table I.2 25 Table 1005 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is ethoxy, yc is CHGC(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a cvl"~o~nd corresponds to a group of Table I.2 Table 1006 Compounds of the general formula I.C (n s 0) in which UR' is ethylamino, VR" i8 ethoxy, yc is CH=C(Cl)-C(=0)-NH-~ (-# e bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1007 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxy, VR is methylamino, yc is CH=C(Cl)-C(=o)-NH-# (-# ~ bond to AC) and Ac for a cv...~ound corresponds to a group of Table I.2 ':
~5~/45~4 -283 21g9 122 Table 1008 Compounds of the general formula I.C (n - 0) in which UR' i~
ethoxy, VR~' is ~ethylamino, yc is CH=C(Cl)-C(-O)-NH-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1009 Compounds of the general formula I-C (n 3 O) in which UR' is 10 methoxy, VR" is ethylamino, yc is CH-C(Cl)-C(-O)-NH-# (-# = bond to AC) and Ac for a ~o,..~ound corresponds to a group of Table I.2 Table 1010 15 Compounds of the general formula I.C (n - 0) in which UR' is ethoxy, VR" is ethylamino, yc i8 CH-C(Cl)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1011 Compo~nds of the general formula I.C (n ~ O) in which UR' i8 methoxy, VR" is methoxy, yc is CH=C(Br)-C(=O)-NH-# (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 25 Table 1012 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR i5 methoxy, yc is CH=C(Br)-C(=O)-NH~ - bond to AC) and Ac for a cG.,.poulld corresponds to a group of Table I.2 Table 1013 Compounds of the general formula I.C (n = 0) in which UR' i8 methoxy, VR" is ethoxy, yc is CH=C(Br)-C(=O)-NH-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1014 C~ oul,ds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR is ethoxy, yc is CH3C(Br)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 -284 ~199~22 Table 1015 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" i8 methoxy, yc is CH=c(Br)-ct=o)-NH-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1016 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethylamino, VR" i8 methoxy, yc is CH--C(Br)-C(=0)-NH~ # = bond to A~) and Ac for a cv...pound corresponds to a group of Table I.2 Table 1017 15 Compounds of the general formula I.C (n s 0) in which UR' is f methylamino, VR" is ethoxy, yc is CH=C(Br)-C(=0)-NH-# (-~ 5 bond to AC) and Ac for a c~ o~"d corresponds to a group of Table I.2 Table 1018 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc i8 CH=c(Br)-c(=o)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1119 Co~ ou,lds of the general formula I.C (n = 0) in which UR' is ~ methoxy, VRn i8 methylamino, yc is CH-C(Br)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 f~ Table 1020 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methylamlno, yc is CH-C(Br)-C(=0)-NH-# (-~ = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1021 Co...~Gunds of the general formula I.C (n = 0) in which UR' i~
40 methoxy, VRn i8 ethylamino, yc i8 CH=C(Br)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I
O0~0/45204 ~ 285 2199122 Table 1022 Compounds of the general formula I.C (n = ~) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(Br)-C(20)-NH-$ (-~ = bond to AC) and Ac for a cv,.~ound corresponds to a group of Table I.2 Table 1023 Co..,~ounds of the general formula I.C (n = 0) in which UR' is 10 methoxy, VRn i8 methoxy, yc is CH=C(CN)-C(=O)-NH-# (-# 3 bond to AC) and Ac for a co,.,pou-~d corresponds to a group of Table I.2 Table 1024 15 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methoxy, yc i8 CH=C(CN)-C(=O)-NH-# (-# ~ bond to AC) and Ac for a cv..~oul~d corresponds to a group of Table I.2 Table 1025 ~0 Col"p~unds of the general formula I.C (n ~ 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1026 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc i8 CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~- Table 1027 . . . = .
Co.~,~Gunds of the general formula I.C (n - 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(CN)-C(=O)-NH-# (-# ~ bond 35 to AC) and Ac for a co..,~o~.d corresponds to a group of Table I.2 Table 1028 ~
Compounds of the general formula I.C (n = 0) in which UR' is 40 ethylamino, VR" is methoxy, yc is CHsC(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 ~5~/45~4 - - -~ 286 2~99~1~2 Table 1029 Compounds of the general formula I.C (n = 0) in which UR' i9 methylamino, VR" is ethoxy, yc i8 CH=c(cN)-c(=o)-NH-# (-~ = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1030 Compounds of the general formula I.C (n - 0) in which UR' is lO ethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=O)-NH-~ = bond to AC) and Ac for a cv~ ound corresponds to a group of Table I.2 Table 1031 15 C~".~ou-~ds of the general formula I.C (n = 0) in which UR' is { methoxy, VRn is methylamino, yc is CH=C(CN)-C(=O)-NH-# (-~ = bond to AC) and Ac for a co.l.~ou.-d corresponds to a group of Table I.2 Table 1032 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=c(cN)-c(=o)-NH-# ~ bond to AC) and Ac for a cv...~ound corresponds to a group of Table I
25 Table 1033 C~,.~oullds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a o...~oulld corresponds to a group of Table I.2 f~ Table 1034 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-NH-$ (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1035 Compounds of the general formula I.C (n = o) in which UR' is 40 methoxy, VR" is methoxy, yc is CH=C(NO2)-C(=O)-NH-~ bond to AC) and Ac for a co..,pGund corresponds to a group of Table I.2 -287 219912~
Table 1036 Co~ ounds of the general formula I.C (n z 0) in which UR~ is ethoxy, VR" is methoxy, yc is CH=C(N02)-C(-0)-NH-# (-# 2 bond to 5 AC) and Ac for a compound corresponds to a group of.Table I.2 Table 1037 Compounds of the general formula I.C (n = 0) in which UR' i~
10 methoxy, VR" is ethoxy, yc is CH~C(No2)-c(=o)-NH-$ (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1038 15 Compounds of the general formula I.C (n 5 O) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(G0)-NH-# (-~ = bond to AC) and Ac for a cor,.~oulld corresponds to a group of Table I.2 Table 1039 Compounds of the general formula I.C (n = 0) in which UR' i8 methylamino, VR" is methoxy, yc i8 CH-C(N02)-C(=0)-NH-~ bond to AC) and Ac for a ~l.*~u~.d correspond~ to a group of Table I.2 25 Table 1040 Compounds of the general ~ormula I.C (n - 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C(N02)-C(=0)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 . Table 1041 Compounds of the general formula I.C (n ~ 0) in which UR' is methylamino, VR" is ethoxy, yc i8 CHeC(NO2)-C(=O)-NH-# (-# = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1042 Compounds of the general formula I.C (n - 0) in which UR' i5 40 ethyla~ino, VRn iS ethoxy, yc is CHsC(N02)-C(=O)-NH-~ = bond to AC) and Ac for a co~ o~lld corresponds to a group of Table I.2 ~ 288 ?199 1~2 ~able 1043 Compounds of the general formula I.C (n s 0) in which UR' is methoxy, VR" is methylamino, yc is CH2C~No2)-C(eO)-NH-# (-# 5 bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1044 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is methylamino, yc is CH=C(N02)-C(sO)-NH-# (-~ = bond to AC) and Ac for a co~.,p~ld corresponds to a group of Table I.2 .
Table 1045 15 Compounds of the general formula I.C (n = o) in which UR' is methoxy, VR" is ethylamino, yc is CH=c(No2)-c(=o)-NH-# (-~ = bond to AC) and Ac for a cG.,*ound corresponds to a group of Table I.2 Table 1046 Co,-~u~lds of the general formula I.C (n ~ 0) in which UR' is ethoxy, VR" i8 ethylamino, yc is CH=C(N02)-C(=0)-NH-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1047 Compounds of the general formula I.C (n = 0) in which UR~ is methoxy, VR" is methoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-# = bond to AC) and Ac for a co...~ound corresponds to a group of Table I.2 f_ Table 1048 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methoxy, yc is CH=C(Cl)-c(=o)-N(CH3)-# (-# 5 bond 35 to AC) and Ac for a cn.~_und corresponds to a group of Table I.2 Table 1049 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxy, VR~' is ethoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 289 2199~22 Table 1050 Compounds of the general formula I.C (n - 0) in whieh UR' is ethoxy, VR" is ethoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-~ = bond to 5 AC) and Ac for a eompound eorresponds to a group of Table I.2 Table 1051 Compounds of the general formula I.C (n = 0) in whieh UR' i8 10 methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a oo..~o~nd eorresponds to a group of Table I.2 Table 1052 Compounds of the general formula I.C (n 2 O) in whieh UR' is ethylamino, VR" is methoxy, yc i8 CH2C(Cl)-C(=O) -N(CH3)-# (-# =
bond to AC) and Ac for a ev~-~ound eorresponds to a group of Table I.2 Table 1053 Co..,pounds of the general formula I.C (n - 0) in whieh UR' is methylamino, VR" i~ ethoxy, yc is CH=C(Cl)-C(=O)-N(CH3)-~ (-# =
25 bond to AC) and Ac for a evl..pound eorresponds to a group of Table I.2 Table 1054 30 Cor..pGunds of the general formula I.C (n - 0) in whieh UR' is r ethylamino, VR" is ethoxy, yc is CH=C(Cl)-C(=O)-N(CH3)-~ (-# =
bond to AC) and Ac for a eompound eorresponds to a group of Table I.2 35 Table 1055 Compounds of the general formula I.C (n = 0) in whieh UR' is methoxy, VR" is methylamino, yc is CH=C(Cl)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a eor,.~und eorresponds to a group of Table 40 I.2 Table 1056 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
5 bond to A~) and Ac for a compound corresponds to a group of Table I.2 Table 1057 10 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a co...~ur.d corresponds to a group of Table I.2 15 Table 1058 co...~unds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 ethylamino, yc is CHsC(Cl)-C(=O)-N(CH3)-# (-# =
bond to AC) and Ac for a ~ und corresponds to a group of Table 20 I.2 Table 1059 Compounds of the general formula I.C (n - 0) in which UR' i8 25 methoxy, VR" is methoxy, yc is CH2C(Br)-C(=O)-N~CH3)-# (-# = bond to AC) and Ac for a ~v...~ou,ld corresponds to a group of Table I.2 Table 1060 30 C~,..pounds of the general formula I.C (n = 0) in which UR' is ~- ethoxy, VR" is methoxy, yc -~s CH=C(Br)-C(=0)-N(CH3)-# (-~ = bond to AC) and Ac for a co...~ul~d corresponds to a group of Table I.2 Table 1061 Co~.~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethoxy, yc is CH=C( Br)-C(=0)- N(CH3) -# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 40 Table 1062 Co...~ou~lds of the general formula I.C (n = 0) in which UR' iY
ethoxy, VR" is ethoxy, yc is CH=c(Br)-c(=o)-N(cH3)-# (-# = ~ond to AC) and A~ for a compound corresponds to a group of Table I.2 ~ 291 2199~22 Table 1063 Compounds of the general formula I.C (n - 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(~r)-C(=0) - N ( CH3 ) -# ( -# =
5 bond to AC~ and Ac for a compound corresponds to a group of Table I.2 Table 1064 10 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C( Br)-C(=0) -N(CH3)--# (-# =
bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 15 Table 1065 ~' Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VRn is ethoxy, yc is CH=C(Br)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a cv..*~u~ld corresponds to a group of Table 20 I.2 Table 1066 CG~ o~nds of the general formula I.C (n = 0) in which UR' is 25 ethylamino, VR" i5 ethoxy, yc is CH=C(Br)-C(=0)-N(CH3)-~bond to AC) and Ac for a c. oul~d corresponds to a group of Table I.2 Table 1067 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH-C(Br)-C(=O) - N(CH3)-~ ( - # -bond to A~) and Ac for a c_ ound corresponds to a group of Table I.2 Table 1068 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yc is CH=C (3r)-C(=0)-N(CH3)-# (-$ =
40 bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~ 292 2 1 9 9 ~ 2 2 Table 1069 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(Br)-C(=0)-N(CH3)-# (-# =
5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1070 10 CG~.pounds of the general formula I.C (n = 0) in which UR' is ethoxy, VRn is ethylamino, yc is CH=C(Br)-C(=0)-N(CH3)-#. (-# =
bond to AC) and Ac for a c~".~vund corresponds to a group of Table I.2 15 Table 1071 r ~-- C~."~oul~ds of the general formula I.C (n = 0) in which UR' is ~ethoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# = bond to AC) and Ac for a col"~o~.d corresponds to a group of Table I.2 Table 1072 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-~ (-# = bond 25 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1073 CG11~Ur1dS of the general formula I.C (n = 0) in which UR' is 30 methoxy, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# = bond _. to AC) and Ac for a cG.. ~o~l~d corresponds to a group of Table I.2 Table 1074 35 Compounds of the general formula I.C tn = 0) in which UR' is ethoxy, VR is ethoxy, yc is CH=c(cN)-c(=o)-N(cH3)-# (-~ 2 bond to AC) and Ac for a co...~o~-d corresponds to a group of Table I.2 Table 1075 Compounds of the general formula I.C (n ~ 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(CN)-C(-0)-N(CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 293 2199~22 Table 1076 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CHsC(CN)-C(=0)-N(CH3)-~
5 bond to AC) and A~ for a compound corresponds to a group of Table I.2 Table 1077 10 Compounds of the general formula I.C (n = 0) in which UR' ismethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a co~ ound corresponds to a group of Table I.2 15 Table 1078 ( Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table 20 I.2 Table 1079 Co.,.pounds of the general formula I.C (n = 0) in which UR' is 25 methoxy, VR" is methylamino, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1080 Co",~ou~lds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methylamino, yc is CH=C(CN)-C(=O)-N(CH3)-~ 3 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1081 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-N(CH3)-~ (-# =
40 bond to AC) and Ac for a compound corresponds to a group of Table I.2 -0050/452~4 ~ 294 2199~22 Table 1082 Co"l~o~nds of the general formula I.C (n 5 0) in which UR' is ethoxy, VR" is ethylamino, yc i~ CH=CtCN)-C(=O)-N(CH3)-# ~-# 5 5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1083 10 C~."~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH=C(N02)-C( 50)-N(CH3)-~ t-# = bond to AC) and AC.for a compound corresponds ~o a group of Table I.2 Table 1084 lS
( Com~ounds of the general formula I.C (n - 0) in which UR' is - ethoxy, VR" is methoxy, yc is CH=C(N02)-C(-0)-N(CH3)-~ (-# = bond to AC) and Ac for a c~ oul~d corresponds to a group of Table I.2 20 Table 1085 Compounds of the general formula I.C In = 0) in which UR' is methoxy, VR" is ethoxy, yc is CH-C(N02)-C(=0)-N(CH3)-# (-# - bond to AC) and Ac for a co,.,~ou,~d corresponds to a group of Table I.2 Table 1086 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(=0)-N(CH3)-~ (-# - bond 30 to AC) and Ac for a c~ oul-d corresponds to a group of Table I.2 Table 1087 ~
Compounds of the general formula I.C (n - 0) in which UR' is 35 methylamino, VR" is methoxy, yc is. CH=C(N02)-C(sO)-N(CH3)-# (-# -bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1088 CG..,~o~nds of the general formula I.C (n - 0) in which UR' is ethyl.~mino, VR" is methoxy, yc is CH2C(N02)-C(=0)-N(CH3)-# (-# -bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~5 -~ 295 219~'122 Table 1089 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, ~R" i8 ethoxy, yc is CH=C(NO2)-C(=O)-N(CH3)-# (-# =
5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1090 10 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" i8 ethoxy, yc is CH=C(NO2)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 lS Table 1091 ( CG...~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" i8 methylamino, yc is CH=C(NO2)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a compound corresponds to a group of Table Z0 I.2 Table 1092 Compounds of the general formula I.C (n = 0) in which UR' is 25 ethoxy, VR" i8 methylamino, yc is CH=C(N02)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1093 Co...~ounds of the general formula I.C (n = 0) in which UR' i8 methoxy, VR" i 8 ethyla~ino, yc is CH=C(N02)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a c~...~ound corresponds to a group of Table I.2 Table 1094 Compounds of the general form~la I.C (n = 0) in ~hich UR' is ethoxy, VR" is ethylamino, yc is CH=C(NO2)-C('O)-N(CH3)-# (-# =
40 bond to AC) and Ac for a cG...~o~nd corresponds to a group of Table I.2 Table I.l 45 No. Ac No. Ac 4 CH(CH3)z CH2CH2CHzCH3 6 CH ( CH3 ) CH2CH3 7 CH2CH ( CH3 ) 2 B C(CH3)3 CHzcH=cH2 1 0 CH2CH=CHCH3 11 . CH2CH-CHCl 12 CH2C = CH
15 14 Cyclopropyl C l S Cyclopentyl 1 6 Cyclohexyl 18 C6Hs--CH2 ~, .
~ 2199~22 Table I.2 No. Ac CH(cH3)2 CH2CH2CH2cH3 10 6 CH(cH3)cH2cH3 7 CH2CH(CH3)2 8 . C(CH3)3 g Cyclopropyl Cyclopentyl 15 11 Cyclohexyl ' 12 C6H5 13 C6Hs-CH2 20 Table 1095 Compounds of the general formula I.D (n = 0) in which UR' is methoxy, VR" is methoxy and Ad for a ~v...~ound corresponds to a group of Table J
Table 1096 Compounds of the general formula I.D (n = 0) in which UR' is ethoxy, VRn is methoxy and Ad for a cv,~,~ound corresponds to a 30 group of Table J
Table 1097 Compounds of the general formula I.D (n = 0) in which UR' is 35 methoxy, VR" is ethoxy and Ad for a compound corresponds to a group of Table J
Table 1098 40 Compounds of the general formula I.D (n = 0) in which UR' is ethoxy, VR" is ethoxy and Ad for a compo~nd corresponds to a group of Table J
0050~45204 298 2 1 9 9il 2 2 Table 1099 Cv.,,pvunds of the general formula I.D (n - 0) in which UR' is methylamino, VR" is methoxy and Ad for a cG...~ound corresponds to a 5 group of Table J
Table 1100 Compounds of the general formula I.D (n ~ 0) in which UR' i8 10 ethylamino, VR~ i8 methoxy and Ad for a c~."po~nd corresponds to a group of Table J
Table 1101 15 Compounds of the general formula I.D (n = 0) in which UR' is ( methylamino, VR" is ethoxy and Ad for a cv.,,p~r~d corresponds to a group of Table J
Table 1102 Compounds of the general formula I.D (n = 0) in which UR' is ethylamino, VR" is ethoxy and Ad for a ~o~,o~.,d corrssponds to a group of Table J
25 Table 1103 Compounds of the general formula I.D (n = 0) in which UR' is methoxy, VR" i8 methylamino and Ad for a ~-v..~oul~d corresponds to a group of Table J
Table 1104 Co...pounds of the general formula I.D (n - 0) in which UR' is ethoxy, VRn is methylamino and Ad for a co..,~o~nd corresponds to a 35 group of Table J
Table 1105 ~
Co~ ounds of the general formula I.D (n e O) in which UR' is 40 methoxy, VRN is ethylamino and Ad for a compound corresponds to a group of Table J
~ ~ 00~/4$204 2199-~22 ~ 29 ~able 1105 Compoun~s o~ th~ ~eneral formula I ;~ (n - 0) in which UR~ is ethoxy, YR" is ~hyl~; n~ and Ad ~ a co~rolln~l cc~rrespon~ tD a 5 gxoup of Table J
Table ~
.. ... . .
Elo. Ae .. ....
10 1 Cyclopropyl , .. ..
~Y~ u~yi 3 Cyclopentyl 4 Cyclt3hexyl 1- ~ 4-OC2tls-C6E~4 ) -2, 2-~12-~y~lo~ropyl l-~H3--2, 2--C12--cyclo~u~
7 1--CF3--cyclopropy 1 8 l-C2H5--cyc loyl opy 1 9 1-~2~CEI3-cyclo~opyl 2C\ ~ 0 1--C~ CH 2--c:y~lv~
11 1- (CE~2-C6~ ~ -cy~lopr~p~l 12 1-{~ -(4--F-C6H4~ ]-~y~l~propyL
13 1--l CH~ ~ 3--F-~ H4 ~ ] -cy~ lopr 4p~ l ~S 14 1- t C~E~2- ~ 4-Cl-C~ -cyclopropyl lS l-t~-(3-Cl-C~H~? ]~cyc~ propyl 16 l-{~H~-[4-C~CH3)~C~ ,]}--~y~lo~ yl 17 1-CE~ cyclop~o~l 3~ 18 2--~H3 cycluy~ yl 1 g 2, 2 ~ --CyClGp ' vp~ 1 1-C~6EI5-~:YC~10~ yl 21 2--CGH5--cyclop~opyl ~ 1- ( 2-~1--C~H4 3--cy~lv~lo~?yl 3s 2 3 1--~ 3--~l--C~H4 )--cyclo~ r U~y 1 24 1- ( 4-Cl-C6~4 ~ -cyclopropyl ~5 1--( 7 ,. 4-C12--t~6H3 ) -cy~ pl4~
2 6 1--t ~, ~--Cl2--C~H3 )--cyclu~lu~ 1 2~ 6--~12--C6H3)~CYC 10PLo~
2~ 5, 4-C1Z-C~3 ~ -CY~ 1U~1 29 1~ ~ 2--F--C:6~1~, )--CYC:1OPrC~PY1 1~ --F--C6H4)~CYCLr-~PY4PYL
;~ 1 1- ( 4 -F-~I4 )--CYC 14~LUYY 1 3 2 1~ ( :~--Br-C~E~4 )--C:YC 1OP1 OP~ 1 ~ 3 1--~ 3 -: 3r-C6H~ y~l~pL o~l .
219~22 34 1-(4-Br-C6H4)-CYC1OPrOPY1 1-(2-CH3-C6H4)-CYC1OPrOPY1 36 1-(3-CH3-C6H4)-CYC1OPrOPY1 5 37 1-(4-CH3-C6H~)-CYC1OPrOPY1 38 1~[2~4_(CH3)2_C6H3]_CYC1OPrOPY1 39 1-t2~5-(CH3)2-C6H3]-CYC1O~LOP~1 1~t2~6~(CH3)2~C6H3]-CYC1OPrOPY1 41 1-t3~4-(CH3)2-C6H3]-CYC1OPrOPY1 1-~4-C(CH3)3-C6H4]-CYC1OPrOPY1 43 1-(3-CF3-C6H4)-CYC1OPrOPY1 44 1-(2-OCH3-C6H4)-CYC1OPrOPY1 1-(3-OCH3-C6H4)-CYC1OPrOPY1 15 46 1-(4-OCH3-C6H4)-CYC1OPLO~Y1 ( 47 1-12~4-(OCH3)2-C6H3]-CYC1~Pr~PY1 48 1-~2~S-(OCH3)Z-C6H3]-CYC1OPrOPY1 49 1~t2~6~(OCH3)2-C6H3]-CYC1OPrOPY1 20 50 1_t3~4_(0CH3)2-C6H3]-CYC1OPL~1 51 2,2-(CH3)2-CYC1OPrOPY1 52 2~2~(CH3)2~3~~CH=C(CH3)2]-CYC1OPrOPY1 53 2~2~(CH3)2~3~(CH=CC12)-CYC1OPrOPY1 2~2~(CH3)2-3-(CH=CBr2)-CYC1OPrOPY1 2~2~(CH3)2~3~(CH2CC1-CF3)-CYC1OPrOPY1 56 2~2-C12-3~3-(CH3)2-CYC1OPrOPY1 57 2~2~3~3-(CH3)4-CYC1OPrOPY1 58 2~2~(CH3)2~3~(CH=CF2)-CYC1OPrOPY1 30 59 2~2~(CH3)2~3~(CH3CF-CF3)-CYC1OPrOPY1 f~ 60 2~2~(CH3)2~3~~CH=C(CH3)-CO2CH3]-CYC10PrOPY1 61 2~2~(CH3)2~3~(CH=CHCH=CC12)-CYC1OPrOPY1 62 2,2-(CH3)2-3-(CHBrCBr3)-cyclopropyl 35 63 2~2-(CH3)Z-3- (cHBrccl2Br)-cyclopropyl 64 2,2-(CH3)2-3-(CYC1OPentY1idenemethY1)-CYC1OPrOPY1 2~2-(CH3)2-3-[4-C(CH3)3-C6H4]-CYC1OPrOPY1 40 Tab1e 1107 COmPOUndS Of the genera1 fOrmU1a I.E (n = 0) in WhiCh UR' ~S
methOXY~ VR" is methOXY~ ye is ~CH-NO~~ (~# = bOnd to Ae) and Ae fOr a COmPOUnd COrreSPOndS tO a grOUP Of Tab1e K.1 UV~/4~U4 ~ 301 2199'122 Table 1108 Compounds of the general formula I.E (n = 0) in which UR' is ethoxy, VR" is methoxy, ye is -CHzNO-# (~~ = bond to Ae) and Ae 5 for a c~ po~L.d corresponds to a group of Table K.1 Table 1109 Compounds of the general formula I.E (n = 0) in which UR' is 10 methoxy, VR" i8 ethoxy, ye is -CH2N0-~ = bond to Ae) and Ae for a compound corresponds to a group of Table K.l Table 1110 15 CoA,.~oullds of the general formula I.E (n = 0) in which UR' is C ethoxy, VR" is ethoxy, YQ is -CHsN0-# (-~ = bond to Ae) and Ae for a co,l,pound corresponds to a group of Table R.l Table 1111 Compounds of the general formula I.E (n = 0) in which UR' is methylamino, VR" is methoxy, ye is -CH5NO~ = bond to Ae) and Ae for a ~v..,~ol~nd corresponds to a group of Table K.l 25 Table 1112 Compounds of the general formula I.E (n 5 O) in which UR~ is ethylamino, VR is ~ethoxy, ye i8 -CH=NO-# (-~ = bond to Ae) and Ae for a co,.,~oul,d corresponds to a group of Table K.l f- Table 1113 ., Cc~ ou--ds of the general formula I.E (n = 0) in which UR~ is methylamino, VR" is ethoxy, ye is -CH=NO-~ z bond to Ae) and 35 Ae for a co.,.pound corresponds to a group of ~able K.l Table 1114 Compounds of the general formula I.E (n = 0) in which UR' is 40 ethylamino, VR" is ethoxy, ye is -CH=NO-~ = bond to A~) and Ae for a co...~nd corresponds to a group of Table K.l u~ls~ u~
~ 302 ~ 1 9 g ~ 2 2 Table 1115 Compounds of the general formula I.E (n = 0) in which UR' is methoxy, VR" is methylamino, ye is -CH=NO-# ( - ~ = bond to Ae) and 5 Ae for a compound corresponds to a group of Table K.l Table 1116 Compounds of the general formula I.E (n - 0) in which UR' is 10 ethoxy, VR" i~ methylamino, ye i8 -CH=N0-* (-# = bond to Ae) and Ae for a compound corresponds to a group of Table X.l Table 1117 15 Compounds of the general formula I.E (n ~ 0) in which UR' i8 methoxy, VR" is ethylamino, ye is -CH=No-$ (-# ~ bond to Ae) and ~ A' for a ~v.. ~o~nd corresponds to a group of Table K.l Table 1118 Compounds of the general formula I.E (n = o) in which UR' is ethoxy, VR" i8 ethylamino, ye is -CH=N0-# (-# = bond to Ae) and Ae for a cG,..~ou.ld corresponds to a group of Table K.l 25 Table 1119 Compounds of the general formula I.E (n = 0) in which UR' is methoxy, VR~ is methoxy, Y~ is -CH=N-NH-~ t-# = bond to Ae) and A~
for a compound corresponds to a group of Table K.2 - Table 1120 Compounds of the general formula I.E (n 2 O) in which UR' is ethoxy, VRn is methoxy, ye is -CHsN-NH-~ (-# = bond to Ae) and Ae 35 for a compound corresponds to a group of Table X.2 Table 1121 Compounds of the general formula I.E (n 5 0) in which UR' is 40 methoxy, VR" is ethoxy, ye is -CH=N-NH-~ = bond to Ae) and Ae for a compound corresponds to a group of Table K.2 0~50/4S2~4 219~422 Table 1122 Compounds of the general formula I.E (n = 0) in which UR' is ethoxy, VR" is ethoxy, ye iS -CH=N-NH-~ (-# = bond to Ae) and Ae 5 for a compound corresponds to a group of Table K.2 Table 1123 Compounds of the general formula I.E (n = 0) in which UR' is 10 methylamino, VR" is methoxy, ye is -CH=N-NH-~ 5 bond to Ae) and AQ for a cor..~ound corresponds to a group of Table K.2 Table 1124 15 c~ o~nds of the general formula I.E (n - 0) in which UR' is ' ethylamino, VR" is methoxy, ye iS -CH~N-NH-* (-# - bond to Ae) and Ae for a cv"~o~nd corresponds to a group of Table K.2 Table 1125 Compounds of the general formula I.E (n = 0) in which UR' is methylamino, VR" is ethoxy, ye is -CH=N-NH-# (-# = bond to Ae) and Ae for a c~,..~o~nd corresponds to a group of Table K.2 25 Table 1126 CGl.L~vunds of the general formula I.E (n = 0) in which UR' is ethylamino, VR" is ethoxy, ye i8 -CH=N-NH-~ = bond to Ae) and Ae for a compound corresponds to a gxoup of Table K.2 ~- Table 1127 Cc~ ullds of the general formula I.E (n = 0) in which UR' is methoxy, VR" is methylamino, ye i8 -CH=N-NH-# (-# = bond to Ae) 35 and Ae for a compound corresponds to a group of Table K.2 Table 1128 r~- lunds of the general formula I.E (n = 0) in which UR' i8 40 ethoxy, VR~ is methylamino, ye iS -CH=N-NH-~ = bond to Ae) and A~ for a compound corresponds to a group of Table K.2 2199~22 Table 1129 CGu~ou,lds of the general formula I.E (n = 0) in which UR~ is methoxy, VR" i~ ethylamino, ye is -CH=N-NH-# (-# = bond to Ae) and 5 Ae for a compound corresponds to a group of Table K.2 Table 1130 Compounds of the general formula I.E (n = 0) in which UR' is 10 ethoxy, VR" is ethylamino, ye is -CH=N-NH~ = bond to AQ) and Ae for a compound corresponds to a group of Table K
Table K.l 15 Compound No. R2 t 1.467 H
1.468 CH3 1.469 CH3CH2 1.470 CH3CH2CH2 1.471 CH2ZcH-cH2 1.472 CH3-CH=CH
1.473 CH3-CH=CH-CH(CH3) 1.474 FH3 HC_C l = CH C
1.475 HC_C-CH2 1.476 CH3-O-CH2-CH2 1.477 C2Hs-o-cH2-cH2 30 1.478 Cl-CH2-CH2 1.479 Cyclo-c3Hs-cH2 1.480 CH3-cH=cH-cH2 1.481 CH2=cH-cH2-cH2 35 1.482 CH3C_C-cH2 1.483 CH3CH2-C-C-cH2 1.484 CH3-(CH2)3 1.485 CH3-(CH2)4 40 1.486 (CH3)3C
1.487 Cyclo-C6Hll 1.488 2-CH3-Cyclo-CcH1o 1.489 C6Hs-CH2 4 1.490 2-F-C6H4-CH2 1.491 3-F-C6H4-CH2 1.492 4-F-C6H4-CH2 0050/45204 2 ~ 9 9 i 2 2 COI..~O~nd NO. R2 1.493 2-cl-c6H4-cH2 1.494 3-cl-C6H4-CH2 5 1.495 4-Cl-C6H4-CH2 1.496 2,3-cl2-c6H3-cH2 1.497 2,4-cl2-C6H3-cH2 1.498 2,5-Cl2-C6H3-CH2 1.499 2,6-cl2-C6H3-cH2 1.500 3,4-cl2-c6H3-cH2 1.501 2-CH3-c6H4-cH2 1.502 3-CH3-C6H4-CH2 1.503 4-cH3-c6H4-cH2 15 1.504 2,3-(CH3)2-C6H3-CH2 (1.505 2,4-(CH3)2-C6H3-CH2 1.506 2,5-(CH3)2-C6H3-CH2 1.507 3,4-(CH3)2-C6H3-CH2 20 1.508 3,5-(CH3)2-C6H3-CH2 1.509 4~5-(CH3)2-C6H3-CH2 1.510 2,3,4-(CH3)3-C6H2-CH2 1.511 2,4,5-~CH3)3-C6H2-CH2 25 1.512 2,4,6-(CH3)3-C6H2-CH2 1.513 2,3,6-(CH3)3-C6H2-CH2 1.514 2-CF3-C6H4-CH2 1.515 3-CF3 C6H4-CH2 1.516 4-CF3-C6H4-CH2 30 1.517 2-CH3-3-CF3-C6H3-CH2 1.518 2-CH3-4-CF3-C6H3-CH2 1.519 2-CF3-3-CH3-C6H3-CH2 1.520 2-CF3-4-CH3-C6H3-CHz 35 1.521 2-CF3-5-CH3- 4 H3-CH2 1.522 2--CH3--5--CF3--C6H3--CH2 1.523 2-Br-C6H4-CH2 1.524 3-Br-C6H4-CH2 40 1.525 4-Br-C6H4-CH2 1.526 2-(iso-Propyl)-C6H4-CH2 1.527 3-(iso-propyl)-c6H4-cH2 1.528 4-(iso-Propyl)-C6H4-CH2 1.529 2-(iso-Propyl)-3-Cl-C6H3-CH2 1.530 2-(iso-Propyl)-4-Cl-C6H3-CH2 1.531 2-(iso-Propyl)-5-Cl-C6H3-CH2 0050/45204 2 1 9 9 4 ~ 2 Compound No. R2 1.532 2-cH3-3-(iso-propyl)-c6H3-cH2 1.533 2-CH3-4-(iso-Propyl)-C6H3-CH2 5 1.534 2-CH3-5-(iso-Propyl)-C6H3-CH2 1.535 2-t-C4Hg-C6H4-CH2 1.536 3-t-C4H9-C6H4-CH2 1.537 4-t-C4Hg-C6H4-CH2 1.538 2-CH3-3-t-C4H9-C6H3-CHz 1.539 2-CH3-4-t~C4Hs~C6H3~CH2 1.540 2-CH3-5-t-C4Hg-C6H3-CH2 1.541 3-CH3-4-t-C4Hg-C6H3-CH2 1.542 3-CH3-5-t-C4Hg-C6H3-CH2 15 1.543 2-cl-3-t-c4H9-c6H3-cH2 1.544 2-cl-4-t-c4H9-c6H3-cH2 1.545 2-cl-5-t-c4H9-c6H3-cH2 1.546 3-Cl-4-t-C4Hs~C6H3~CH2 20 1.547 3-Cl-5-t-C4Hg-C6H3-CH2 1.548 2-OCH3-C6H4-CH2 1.549 3-OCH3-C6H4-CH2 1.550 4-OCH3-c6H4-cH2 25 1.551 2-CH3-3-0CH3-C6H3-CH2 1.552 2-CH3-5-0CH3-C6H3-CH2 1.553 3-CH3-4-0CH3-C6H3-cH2 1.554 3-CH3-5-0CH3-C6H3-cH2 1.555 2-Cl-3-0CH3-C6H3-CH2 30 1.556 2-Cl-4-0CH3-C6H3-CH2 1.557 2-C1-5-OCH3-C6H3-CH2 1.558 2-ocH3-3-cl-c6H3-cH2 1.559 2-ocH3-4-cl-c6H3-cH2 35 1.560 2-OCH3-5-Cl-C6H3-CH2 1.561 2-CH3-4-(Cyclohexyl)-C6H3-CH2 1.562 2-CH3-4-C6H5-C6H3-CH2 1.563 2-CH3-3-Br-C6H3-CH2 40 1.564 2-CH3-4-Br-C6H3-CH2 1.565 2-CH3-5-Br-C6H3-CH2 1.566 2-CH3-3-(methoxyiminoethyl)-C6C3-CH2 1.567 2-methoxyiminoethyl-C6H4-CH4 1.568 3-methoxyiminoethyl-C6H4-CH4 1.569 2-CH3-4-(methoxyiminoethyl)-C6H3-CH2 1.570 2-Phenyl-C6H4-CH2 0050/45204 2 1 9 ~ ~ 2 2 Col,.pound No. RZ
1.571 3-Phenyl-C6H4-CH2 1.572 4-Phenyl-C6H4~CH2 5 1.573 2-Phenoxy-C6H4~CH2 1.574 3-PhenoXy-c6H4-cH2 1.575 4-Phenoxy-c6H4-cH2 1.576 2-Benzyloxy-C6H4-CH2 1.577 3-BenzyloXy-c6H4-cH2 1.578 4-Benzyloxy-c6H4-cH2 1.579 l-Naphthyl-CH2 1.580 2-Naphthyl-CH2 1.581 9-Anthryl-CH2 15 1.582 2-CH3-3-C6HsO~C6H3~CH2 1.583 2-CH3-4-C6H50-C6H3-CH2 1.584 2-CH3-5-C6HsO-C6H3-CH2 1.585 3-CH3-4-C6H50-C6H3-CH2 20 1.586 4-CH3-5-C6HsO~C6H3~CH2 1.587 2-Cl-3-C6H50-C6H3-CH2 1.588 2-Cl-4-C6H50-C6H3-CH2 1.589 2-Cl-5-C6H50-C6H3-CH2 25 1.590 3-Cl-4-C6H50-C6H3-CH2 1.591 3-Cl-5-C6H50-C6H3-CH2 1.592 2-CH3-4-C02CH3-C6H3-CH2 1.593 2-CH3-5-C02CH3-C6H3-CH2 1.594 C6H5-CH(CH3) 30 1.595 2-F-C6H4-CH(CH3) .1.596 2-F-C6H4-CH(CH3) 1.597 4-F-C6H4-CH(CH3) 1.598 2-C1-C6H4-CH~CH3) 35 1.599 3-Cl-C6H4-CHtCH3) 1.600 4-C1-C6H4-CH(CH3) 1.601 2,3-Cl2-C6H3-CH(CH3) 1.602 2,4-Cl2-C6H3-CH(CH3) 40 1.603 2,5-Cl2-C6H3-CH(CH3) 1.604 2,6-C12-C6H3-CH(CH3) 1.605 3,4-Cl2-C6H3-CH(CH3) 1.606 2-CH3-C6H4-CH(CH3) 1.607 3-CH3-C6H4-CH(CH3) 1.608 4-CH3-C6H4-CH(CH3) 1.609 2,3-(CH3)2-C6H3-CH(CH3) -0050~45204 ~ 2199 122 Compound No. R2 1.610 2,4-(CH3)2-C6H3-CH(CH3) 1.611 2,5-(CH3)2-C6H3-CH(CH3) 5 1.612 3,4-(CH3)2-C6H3-CH(CH3) 1.613 3,5-(CH3)2-C6H3-CH(CH3) 1.614 4~5-(cH3)2-c6H3-cH(cH3) 1.615 2,3,4-(CH3)3-C6H2-CH(CH3) 1.616 2,4,5-(CH3)3-C6H2-CH(CH3) 1.617 2,4,6-(CH3)3-C6Hz-CH(CH3) 1.618 2,2,6-(CH3)3-C6H2-CH(CH3) 1.619 2-CF3-C6H4-CH(CH3) 1.620 2-CF3-C6H4-CH(CH3) 15 1.621 4-CF3-C6H4-CH(CH3) 1.622 2-CH3-3-CF3-C6H3-CH(CH3) 1.623 2-CH3-4-CF3-C6H3-CH(CH3) 1.624 2-CF3-3-CH3-C6H3-CH(CH3) 20 1.625 2-CF3-4-CH3-C6H3-CH(CH3) 1.626 2-CF3-5-CH3-C6H3-CH(CH3) 1.627 2-CH3-5-CF3-C6H3-CH(CH3) 1.628 2-Br-C6H4-CH(CH3) 25 1.62g 3-Br-C6H4-CH(CH3) 1.630 4-Br-C6H4-CH(CH3) 1.631 2-(iso-Propyl)-C6H4-CH(CH3) 1.632 3-(iso-Propyl)-C6H4-CH(CH3) 1.633 4-(iso-Propyl)-C6H4-CH(CH3) 30 1.634 2-(iso-Propyl)-3-Cl-C6H3-CH(CH3) 1.635 2-(iso-Propyl)-4-Cl-C6H3-CH(CH3) 1.636 2-(iso-Propyl)-5-Cl-C6H3-CH(CH3) 1.637 2-CH3-3-(iso-Propyl)-C6H3-CH(CH3) 35 1.638 2-CH3-4-(iso-Propyl)-C6H3-CH(CH3) 1.639 2-CH3-5-(iso-Propyl)-C6H3-CH(CH3) 1.640 2-t-C4Hg-C6H4-CH-(CH3) 1.641 3-t-C4Hg-C6H4-CH~(CH3) 40 1-642 4-t-C4Hs~C6H4~CH(cH3) 1.643 2-CH3-3-t-C4Hg-C6H3-CH(cH3) 1.644 2-CH3-4-t-C4Hg-C6H3-CH(cH3) 1.645 2-CH3-5-t-C4Hg-C6H3-CH(CH3) 1.646 3-CH3-4-t-C4Hg-C6H3-CH(CH3) 1.647 3-CH3-5-t-C4Hg-C6H3-CH(CH3) 1.648 2-Cl-3-t-C4Hg-C6H3-CH(CH3) .
~199422 Compound No. R2 1.649 2-Cl-4-t-C4Hg-C6H3-CH(CH3) 1.650 3-Cl-4-t-C4Hg-C6H3-CH(CH3) 5 1.651 3-Cl-5-t-C4Hg-C6H3-CH(CH3) 1.652 2-OCH3-C6H4-CH2-CH(CH3) 1.653 3-OCH3-C6H4-CH2-CH(CH3) 1.654 4-OCH3-C6H4-CH2-CH(CH3) 1.655 2-CH3-3-OCH3-C6H3-CH(CH3) 1.656 2-CH3-4-OCH3-C6H3-CH(CH3) 1.657 2--CH3--5--OCH3--C6H3--CH(CH3) 1.658 3-CH3-5-OCH3-C6H3-CH(CH3) 1.659 3-CH3-5-OCH3-C6H3-CH(CH3) lS 1.660 2-Cl-3-OCH3-C6H3-CH(CH3) .1.661 2-Cl-4-OCH3-C6H3-CH(CH3) 1.662 2-Cl-5-OCH3-C6H3-CH(CH3) 1.663 2-0CH3-3-Cl-C6H3-CH(CH3) 20 1.664 2-OCH3-4-Cl-C6H3-CH(CH3) 1.665 2-OCH3-5-Cl-C6H3-CH(CH3) 1.666 2-CH3-4-(Cyclohexyl)-C6H3-CH(CH3) 1.667 2-CH3-4-C6H5-C6H3-CH(CH3) 25 1.668 2-CH3-3-Br-C6H3-CH(CH3) 1.669 2-CH3-4-Br-C6H3-CH(CH3) 1.670 3-CH3-5-Br-C6H3-CH(CH3) 1.671 2~CH3-3-(methoxyiminoethyl)-C6H3-CH(CH3) 1.672 2-methoxyiminoethyl-C6H4-CH(CH3) 30 1.673 3-methoxyiminoethyl-C6H4-CH(CH3) 1.674 2-CH3-4-(methoxyiminoethyl)-C6H3-CH(CH3) 1.675 2-Phenyl-C6H4-CH(CH3) 1.676 3-Phenyl-C6H4-CH(CH3) 35 1.677 4-Phenyl-C6H4-CH(CH3) 1.678 2-Phenoxy-C6H4-CH(CH3) 1.679 3-Phenoxy-C6H4-CH(CH3) 1.680 4-Phenoxy-C6H4-CH(CH3) 40 1.681 2-Benzyloxy-C6H4-CH(CH3) 1.682 3-Benzyloxy-C6H4-CH(CH3) 1.683 4-Benzyloxy-C6H4-CH(CH3) 1.684 1-Naphthyl-CH(CH3) 1.685 2-Naphthyl-CH(CH3) 1.686 9-Anthryl-CH(CH3) 1.687 2-CH3-3-C6H50-C6H3-CH(CH3) .
Compound No. R2 1.688 2-CH3-4-C6H50-C6H3-CHtCH3) 1.689 2-CH3-5-C6H50-C6H3-CH(CH3 5 1.690 3-CH3-4-C6HsO-C6H3-CH(CH3) 1.691 4-CH3-5-C6H50-C6H3-CH(CH3) 1.692 2-Cl-3-C6H50-C6H3-CH(CH3) 1.693 2-Cl-4-C6H50-C6H3-CH(CH3) 1.694 2-Cl-5-C6H50-C6H3-CH(CH3) 1.695 3-Cl-4-C6H50-C6H3-CH(CH3) 1.696 3--Cl--5--C6H50--C6H3--CH(CH3) 1.697 2-CH3-4-C02CH3-C6H3-CH(CH3) 1.698 2-CH3-5-C02CH3-C6H3-CH(CH3) 15 1.699 C6H5-(cH2)2 (1.700 2-F-C6H4-(CHz)2 1.701 2-F-C6H4-(CH2)2 1.702 4-F-C6H4-(CH2)2 20 1.703 2-Cl-C6H4-(CH2)2 1.704 3-Cl-C6H4-(CH2)2 1.705 4-Cl-C6H4-(CH2)2 1.706 2,3-Cl2-C6H3-(CH2)2 25 1.707 2,4-cl2-c6H3-(cH2)2 1.708 2,5-cl2-C6H3-(cH2)2 1.709 2,6-Cl2-C6H3-(CH2)2 1.710 3,4-Cl2-C6H3-(CH2)2 1.711 2-CH3-C6H4-(CH2)2 30 1.712 3-CH3-C6H4-(CH2)2 1.713 4-CH3-C6H4-(CH2)2 1.714 2,3-(CH3)2-C6H3-(CH2)2 1.715 2,4-(CH3)2-C6H3-(CH2)2 35 1.716 2~5-(CH3)z-C6H3-(CH2)2 1.717 3,4-(CH3)2-C6H3-(CH2)2 1.718 3,5-(CH3)2-C6H3-(CH2)2 1.719 4,5-(CH3)2-C6H3-(CH2)2 40 1.720 2,3,4-(CH3)3-C6H2-(CH2)2 1.721 2,4,5-(CH3)3-C6H2-(CH2)2 1.722 2,4,6-(CH3)3-C6H2-(CH2)2 1.723 2,2,6-(CH3)3-C6H2-(CH2)2 1.724 2-CF3-C6H4-(CH2)2 1.725 2-CF3-C6H4-(CH2)2 1.726 4-CF3-C6H4-(CH2)2 2t 99422 Compound No. R2 1.727 2-CH3-3-CF3-C6H3-(cHz)2 1.728 2-CH3-4-CF3-C6H3-(CH2) 1.729 2-CF3-3-CH3-C6H3-(CH2)2 1.730 2--CF3--4--CH3--C6H3--(CH2)2 1.731 2-CF3-5-CH3-C6H3-(CH2)2 1.732 . 2-CH3-5-CH3-C6H3-(CH2)2 1.733 2-Br-C6H4-(CH2)2 1.734 3-Br-C6H4-(CH2) 2 1.735 4-Br-C6H4-(CH2)2 1.736 2-(iso-Propyl)-C6H4-(CH2)2 1.737 3--(iso--Propyl)-C6H4--(CH2) 2 1.738 4--(iso--Propyl )--C6H4--(CH2) 2 ( 1.739 2--(iso--Propyl)--3--Cl--C6H3--(CH2) 2 1.740 2-(iso-Propyl)-4-Cl-C6H3-(CH2)2 1.741 2--(iso--Propyl)-- 5--Cl--C6H3--(CH2)2 1.742 2--CH3--3--(iso--Propyl)-C6H3--(CH2)2 1.7 43 2--CH3--4--(iso-Propyl)-C6H3-(CH2) 2 1.7 44 2--CH3--5--(iso-Propyl)-C6H3-(CH2)2 1.7 45 2--t--C4Hg-C6H4--(CH2)2 1.74 6 3--t--C4Hg-C6H4--(CH2)2 1.747 4-t-C4Hg-C6H4-(CH2)2 1.7 48 2--CH3--3--t--C4Hg--C6H3-(CH2)2 1.749 2-CH3-4-t-c4Hg-c6H3-(cH2)2 1.750 2-CH3-5-t-C4Hg-C6H3-(cH2)2 1.7 51 3--CH3--4--t--C4Hg--C6H3--(CH2)2 1.7 52 3--CH3--5--t--C4Hg--C6H3--(CH2)2 1.7 53 2--Cl--3--t--C4Hg--C6H3--(CH2)2 1.754 2-Cl-4-t-C4Hg-C6H3-(CH2)2 1.755 2-cl-5-t-c4H9-c6H3-(cH2)2 1.75 6 3--Cl--4--t--C4Hg--C6H3--(CH2)2 1.7 57 3--Cl--5--t-C4Hg--C6H3--(CH2)2 1.758 2-OCH3-C6H4-(CH2)2 40 1.759 3-OCH3-C6H4-(CH2)2 1.760 4-OCH3-C6H4-(CH2)2 1.761 2-CH3-3-OCH3-C6H3-(CH2)2 1.762 2-CH3-4-OCH3-C6H3-(CH2)2 1.763 2-CH3-5-OCH3-C6H3-(cH2)2 1.764 3-CH3-4-OCH3-C6H3-(CH2)2 1.765 3-CH3-5-OCH3-C6H3-(CH2)2 0050/45204 2 1 9 9 ~ 2 2 .
C~.llpound No. R2 1.766 2-Cl-3-OCH3-C6H3-(CH3) 2 1.767 2-Cl-4-OCH3-C6H3-(CH3) 2 5 1.768 2-Cl-5-OCH3-C6H3-(CH3)2 1.769 2-ocH3-3-cl-c6H3-(cH3) 2 1.770 2-ocH3-4-cl-c6H3-(cH3)2 1.771 2-ocH3-5-cl-c6H3-(cH3)2 1.772 2-CH3-4-(Cyclohexyl)-C6H3-(CH2)2 1.773 2-CH3-4-C6Hs~C6H3~(CH2) 2 1.774 2-CH3-3-Br-C6H3-(CH2) 2 1.775 2-CH3-4-Br-C6H3-(CH2)2 1.776 3-cH3-5-Br-c6H3-(cH2)2 15 1.777 2-CH3-3-~methoxyiminoethYl)-C6H3-(CH2)2 ;~1.778 2-methoxyiminoethyl~C6H4~(CH2)2 1.779 3--methoxyiminoethyl-C6H4~(CH2)2 1.780 2-CH3-4-(methoxyiminoethyl)-C6H3~(CH2)2 20 1.781 2-Phenyl-C6H4-(CH2)2 1.782 3-Phenyl-c6H4-(cH2)2 1.783 4-Phenyl-c6H4-(cH2)2 1.784 2-Phenoxy-C6H4-(CH2)2 25 1.785 3-Phenoxy-C6H4-(cH2)2 1.786 4-Phenoxy-C6H4~(CH2)2 1.787 2-Benzyloxy-C6H4-(CH2) 2 1.788 2-BenzyloXy-c6H4-(cH2)2 1.789 4-Benzyloxy-C6H4-(cH2) 2 30 1.790 l-Naphthyl-(CH2)2 1.791 2-Naphthyl-(CH2) 2 1.792 9-Anthryl-tCH2)2 1.793 2-CH3-3-C6HsO-C6H3-(CH2) 2 35 1.794 2-CH3-4-C6H5O-C6H3-(CH2)2 1.795 2-CH3-5-C6H50-C6H3-(CH2)2 1.796 3-cH3-4-c6Hso-c6H3-(cH2)2 1.797 4 CH3-5-C6HsO-C6H3-(cH2)2 40 1.798 2-Cl-3-C6HsO-C6H3-(CH2)2 1.799 2-~1-4-C6HSO-C6H3-(CH2)2 1.800 2-Cl-5-C6HsO~C6H3~(CH2)2 1.801 3-Cl-4-C6HSO-C6H3-(CH2)2 1.802 3-Cl-5-C6HsO-C6H3-(CH2)2 1.803 2-CH3-4-C02CH3-C6H3-(CH2)2 1.804 2-CH3-5-C02CH3-C6H3-(CH2)2 0050/45204 ~ ~ 9 9 ~ 2 2 Compound No. R2 1.805 C6H5-cH=cH-cH2 1.806 2-F-c6H4-cH=cH-cH2 5 1.807 3-F-C6H4-CH=CH-CH2 1.808 4-F-C6H4-CH=CH-CH2 1.809 2-Cl-C6H4-CH=CH-CH2 1.810 3-Cl-C6H4-CH=CH-CH2 1.811 4-Cl-C6H4-CH=CH-CH2 1.812 2,3-cl2-c6H3-cH=cH-cH2 1.813 2,4-cl2-c6H3-cH=cH-cH2 1.814 2,5-Cl2-C6H3-CH=CH-CH2 1.815 2,6-Cl2-C6H3-CH=CH-CH2 15 1.816 3,4-Cl2-C6H3-CH=CH-CH2 (1.817 2-CH3-C6H4-CH=CH-CH2 1.818 3-cH3-c6H4-cH2cH-cH2 1.819 4-cH3-c6H4-cH=cH-cH2 20 1.820 2,3-(CH3)2-C6H3-CH=CH-CH2 1.821 2~4-(cH3)2-c6H3-cH=cH-cH2 1.822 2,5-(CH3)2-C6H3-CH=CH-CH2 1.823 3,4-~CH3)2-C6H3-CH=CH-cH2 25 1.824 3,5-(CH3)2-C6H3-CH=CH-CH2 1.825 4,5-(CH3)2-C6H3-CH=CH-CH2 1.826 2,3,4-(CH3)3-C6H2-CH=CH-CH
1.827 2,4,5-(CH3)3-C6H2-CH=CH-CH
1.828 2,4,6-(CH3)3-C6Hz-CH=CH-CH
30 1.829 2,3,6-(CH3)3-C6H2-CH=CH-CH
1.830 2-CF3-C6H4-CH=CH-CH2 1.831 3-cF3-c6H4-cH=cH-cH2 1.832 4-CF3-C6H4-CH=CH-cH2 35 1.833 2-CH3-3-CF3-C6H3-CH=CH-CH2 1.834 2-CH3-4-CF3-C6H3-CH=CH-CH2 1.835 2-CF3-3-CH3-C6H3-CH=CH-CH2 1.836 2--CF3--4--CH3--C6H3--CH=CH--CH2 40 1.837 2-CF3-5-CH3-C6H3-CH3CH-CH2 1.838 2-CH3-5-CF3-C6H3-CH=CH-CH2 1.839 C6Hs-(cH2)3 1.840 C6Hs-(CH2)4 1.841 C6H5-cH2cH=cH-cH2 1.842 4-F-C6H4-CH=CH-(CH2)2 1.843 CH30--CO--CH2 .
Compound No. R2 1.844 CH3CH20-cO-cH2 1.845 CH3-CO-CH2-CH2 5 1.846 t-C4HgO~CO~(CH2)3 1.847 t-C4HgO~CO-(CH2) 2 1.848 t-C4HgO~CO-cH2 1.849 n-C4H9O-CO-CH2 1.850 iso-C4HgO-C0~CH2 1.851 n-C3H7O-CO-CH2 1.852 ~ec.-C4HgO-CO~CH2 1.853 C6H5-CO-CH2 1.854 2-CH3-C6H4O-C0-CH2 15 1.855 3-CH3-C6H4O-cO-cH2 1.856 4-CH3-C6H4O-co-cH2 1.857 2-Cl-C6H4O-cO-cH2 1.858 3-Cl-C6H4O-cO-cH2 20 1.859 4-Cl-C6H4O-cO-cH2 1.860 C6H5-C(CH3)=CH-cH2 1.861 CH2-[pyrid-2-yl]
1.862 CH2-t3-Cl-pyrid-2-yl]
25 1.863 CH2-t4-Cl-pyrid-2-yl]
1.864 CH2-t3-CH3-pyrid-2-yl]
1.86S CH2-t4-CH3-pyrid-2-yl]
1.866 CH2-t3-CF3-pyrid-2-yl~
1.867 CH2-t4-CF3-pyrid-2-yl]
30 1.868 CH2-t3-Br-pyrid-2-yl]
1.869 CH2-[4-Br-pyrid-2-yl]
1.870 CH2-t3-F-pyrid-2-yl]
1.871 CH2-t4-F-pyrid-2-yl]
35 1.872 CH2-tpyrid-3-yl]
1.873 CH2-[2-Cl-pyrid-3-yl]
1.874 CH2-[pyrazin-2-yl]
1.875 CH2-tbenzopyrazin-2-yl]
40 1.876 CH2-[pyridazin-3-yl]
1.877 CH2-t3-CH3, 4-Cl-pyrid-2-yl]
1.878 CH2-t4-CH3, 3-Cl-pyrid-2-yl]
1.879 CH2-t4-CH3, 3-Br-pyrid-2-yl]
1.880 CH2-t6-CH3, 3-Cl-pyrid-2-yl]
1.881 CH2-t6-CH3, 3-Br-pyrid-2-yl]
1.882 CH2-t6-CH3, 3-CH3-pyrid-2-yl]
2~994~2 Cu~ o~ld No. R2 1.883 CH2-t4,6-(CH3)2-pyrid-2-yl]
1.884 CH2-[4-CF3, 3-Cl-pyrid-2-yl]
5 1.885 CH2-t3,6-Cl2-pyrid-2-yl]
1.886 CH2-~3,4-Cl2-pyrid-2-yl]
1.887 CH2-[5-Cl, 6-CH3-pyrid-2-yl]
1.888 CH2-[3-Cl, 4-OCH3-pyrid-2-yl]
1.889 CH2-~3-F, 6-Cl-pyrid-2-yl]
1.890 CH2-[4-Br, 6-NO2-pyrid-2-yl]
1.891 CH2-tfuran-2-yl]
1.892 CH2-[furan-3-yl]
1.893 CH2-~4-Cl-furan-2-yl]
15 1.894 CH2-[pyrrol-2-yl~
1.895 CH2-[pyrrol-3-yl]
1.896 CH2-[l-CH3-pyrrol-2-yl]
1.897 CH2-[l-CH3-pyrrol-3-yl]
20 1.898 CH2-[4,5-benzofuran-2-yl]
1.899 CH2-~4,5-benzothien-2-yl]
1.900 CH2-[pyrazol-5-yl]
1.901 CH2--tisoxazol--5--yl]
25 1.902 CH2-~4-Cl-isoxazol-5-yl]
1.903 CH2-[3-Cl-isoxazol-5-yl]
1.904 CH2-[4-CH3-isoxazol-5-yl]
1.905 CH2-[3-CH3-isoxazol-5-yl]
1.906 CHz-[3-CH3, 4-Cl-isoxazol-5-yl]
30 1.907 CH2-[4-CH3, 3-Cl-isoxazol-5-yl]
1.908 CH2-[thien-2-yl]
1.909 CH2-[thien-3-yl]
1.910 CH2-t3-Cl-thien-2-yl]
35 1.911 CH2-[4-Cl-thien-2-yl]
1.912 CH2-[5-Cl-thien-2-yl]
l.9I3 CH2-tindol-2-yl]
1.914 CH2-[isothiazol-5-yl]
40 1.915 CH2-[4-Cl-isothiazol-5-yl]
1.916 CH2-[3-Cl-isothiazol-5-yl]
1.917 CH2-[2-C6H5-oxazol-4-yl]
1.918 CH2-{2-[2-CH3-C6H4]-oxazol-4-yl}
1.919 CH2-{2-[3-CH3-C6H4]-oxazol-4-yl}
1.920 CH2-{2-[4-CH3-C6H4]-oxazol-4-yl}
1.921 CH2-~2-[2-F-C6H4]-oxazol-4-yl}
0050/45204 2 ~ 9 9 ~ 2 2 Compound No. R2 1.922 CH2-{2-t4-F-C6H4]-oxazol-4-yl}
1.923 CH2-{2-~2-CH3, 4-F-C6H3]-oxazol-4-yl}
5 1.924 CH2-{2-[2-CH3, 4-Cl-C6H3]-oxazol-4-yl}
1.925 CH2-{2-t5-CH3, 2-Cl-C6H3]-oxazol-4-yl}
1.926 CH2-{2-t2-CH3, 4-CH(CH3)2-C6H3]-oxazol-4-yl}
1.927 CH2-{2-~2,4-(CH3)2-C6H3]-oxazol-4-yl}
1.928 CH2-{2-t2,5-(CH3)2-C6H3]-oxazol-4-yl}
1.929 CH2-C--N
1.930 CH2CH=CHCH2-OC(CH3)3 1.931 CH2CH=C(CH3)CH2CH2CH=C(CH3)2 1.932 CH2cHec(cH3)cH2cH2cH=cHcH(cH3) 2 ,., 0050/4s204 2 1 9 9 ~ ~ 2 Table K.2 CG.I.~G1111d NO. R2 5 1.671 R2 1.672 Methyl 1.673 Ethyl 1.674 n-Propyl 1.675 iso-Propyl 1.676 n-Butyl 1.677 i~o-Butyl 1.678 sec-Butyl 1.679 tert-Butyl 15 1.680 n-Hexyl (.1.681 n-Decyl 1.682 Cyclopropyl 1.683 Cyclohexyl 20 1.684 l-Methylcyclopropyl 1.685 l-Methylcyclohexyl 1.686 Ethenyl 1.687 l-Propenyl 25 1.688 2-Methyl-l-propenyl 1.689 2-Propenyl 1.690 2-Butenyl 1.691 Phenyl 1.692 3-Fluorophenyl 1.693 4-Fluorophenyl 1.694 2-Chlorophenyl 1.695 3-Chlorophenyl 1.696 4-Chlorophenyl 35 1.697 Pentachlorophenyl 1.698 2,3-Dichlorophenyl 1.699 2,4-Dichlorophenyl 1.700 2,5-Dichlorophenyl 40 1.701 2,6-Dichlorophenyl 1.702 3,4-Dichlorophenyl 1.703 3,5-Dichlorophenyl 1.704 2,3,4-Trichlorophenyl 1.705 2,3,5-Trichlorophenyl 1.706 2,3,6-Trichlorophenyl 1.707 2,4,5-Trichlorophenyl .
0050/452~4 Compound No. R2 1.708 2,4,6-Trichlorophenyl 1.70g 3,4,5-Trichlorophenyl 5 1.710 2,3~4~5-Tetrachlorophenyl 1.711 2,3,4,6-Tetrachlorophenyl 1.712 2-Bromophenyl 1.713 3-Bromophenyl 1.714 4-Bromophenyl 1.715 2,4-Dibromophenyl 1.716 3-Br~ ~ g fluorophenyl 1.717 3-Bromo-4-methoxyphenyl 1.718 2-iodophenyl 15 1.719 3-iodophenyl 1.720 4-iodophenyl 1.721 2-Chloro-4-fluorophenyl 1.722 2-Chloro-5-fluorophenyl 20 1.723 2-Chloro-6-fluorophenyl 1.724 2-Chloro-4-bromophenyl 1.725 2-BL~- - g chlorophenyl 1.726 2-Br~~ q fluorophenyl 25 1.727 3-BL~_ q-chlorophenyl 1.728 3-Chloro-4-fluorophenyl 1.72g 3-Fluoro-4-chlorophenyl 1.730 2-Cyanophenyl 1.731 3-Cyanophenyl 30 1.732 4-Cyanophenyl f 1.733 2-Nitrophenyl 1.734 3-Nitrophenyl 1.735 4-Nitrophenyl 35 1.736 2-Methylphenyl 1.737 3-Methylphenyl 1.738 4-Methylphenyl 1.739 2,4-Dimethylphenyl 40 1.740 2,5-Dimethylphenyl 1.741 2,6-Dimethylphenyl 1.742 3,4-Dimethylphenyl 1.743 3,5-Dimethylphenyl 1.744 2,3,4-Trimethylphenyl 1.745 2,3,5-Trimethylphenyl 1.746 2,3,6-Trimethylphenyl Compound No. R2 1.747 2,4,5-Trimethylphenyl 1.748 2,4,6-Trimethylphenyl 5 1.749 3,4,5-Trimethylphenyl 1.750 Pentamethylphenyl 1.751 2-Methyl-5-methoxyphenyl 1.752 2-Methyl-6-methoxyphenyl 1.753 2-Methyl-4-iso-propoxyphenyl 1.754 2-Methyl-2,5-dimethoxyphenyl 1.755 2-Methoxyphenyl 1.756 3-Methoxyphenyl 1.757 4-Methoxyphenyl lS 1.758 2,3-Dimethoxyphenyl C 1.759 2~4-Dimethoxyphenyl 1.760 2,5-Dimethoxyphenyl 1.761 2,6-Dimethoxyphenyl 20 1~762 3,4-Dimethoxyphenyl 1.763 3,5-Dimethoxyphenyl 1.764 3,6-Dimethoxyphenyl 1.765 2,3,4-Trimethoxyphenyl 25 1.766 2,3,5-Trimethoxyphenyl 1.767 2,3,6-Trimethoxyphenyl 1.768 2,4,5-Trimethoxyphenyl 1.769 2,4,6-Trimethoxyphenyl 1.770 3,4,5-Trimethoxyphenyl 30 1.771 2-Ethoxyphenyl 1.772 3-Ethoxyphenyl . .
1.773 4-Ethoxyphenyl 1.774 2-iso-Propoxyphenyl 35 1.775 3-iso-Propoxyphenyl 1.776 2-Phenylphenyl 1.777 3-Phenylphenyl 1.778 4-Phenylphenyl 40 1.779 2-Phenoxyphenyl 1.780 3-Phenoxyphenyl 1.781 4-Phenoxyphenyl 1.782 2-Benzyloxyphenyl 1.783 3-Benzyloxyphenyl 1.784 4-Benzyloxyphenyl 1.785 4-(Imidazol-l'-yl)phenyl 0050/45204 - 2 ~ ~ 9 4 2 2 Cvr..~o~nd No. R2 1.786 4-(Piperazin~ yl)phenyl 1.787 4-(Morpholino-l'-yl)phenyl 5 1.788 4-(Piperidinyl-l'-yl)phenyl 1.789 4-(Pyridyl-2'-oxy)phenyl 1.790 2-Cyclopropylphenyl 1.791 3-Cyclopropylphenyl 1.792 4-Cyclopropylphenyl 1.793 3-Cyclohexylphenyl 1.794 4-Cyclohexylphenyl 1.795 4-Oxiranylphenyl 1.796 4-iso-PLopo~y~henyl 15 1.797 3-tert-Butoxyphenyl (1.798 4-tert-~utoxyphenyl 1.799 2-Trifluoromethoxyphenyl 1.800 3-Trifluoromethoxyphenyl 20 1.801 4-TrifluoL~ hoxymethyl 1.802 2-Chloromethylphenyl 1.803 3-Chloromethylphenyl 1.804 4-Chloromethylphenyl 25 1.805 2-Trifluoromethylphenyl 1.806 3-Trifluoromethylphenyl 1.807 4-Trifluoromethylphenyl 1.808 2-(Methoxyiminomethyl)phenyl 1.809 3-(Methoxyiminomethyl)phenyl 30 1.810 4-(Methoxyiminomethyl)phenyl 1.811 2-(Ethoxyiminomethyl)phenyl 1.812 3-(Ethoxyiminomethyl)phenyl 1.813 4-(Ethoxy;m;n~ -thyl)phenyl 35 1.814 2-~n-Propoxyiminomethyl)phenyl 1.815 3-(n-Propoxyiminomethyl)phenyl 1.816 4-(n-Propoxyiminomethyl)phenyl 1.817 2-(iso-Propoxyiminomethyl)phenyl 40 1.818 3-(iso-Propo~yiminomethyl)phen 1.819 2-(Ethoxyimino-1'-ethyl)phenyl 1.820 3-(Ethoxyimino-1'-ethyl)phenyl 1.821 4-(Ethoxyimino-1'-ethyl)phenyl 1.822 2-(n-pLopoxyimino-l~-ethyl)phen 1.823 3-(n-propoxyimino-l~-ethyl)phen 1.824 4-(n-propoxyimino-l'-ethyl)phenyl . , .
~ 2199 i22 Cc"l,~o~nd.No. R2 1.825 2-(n-Butoxyamino-1'-ethyl)phenyl 1.826 3-(n-Butoxyamino-1'-ethyl)phenyl 5 1.827 4-(n-Butoxyamino~ ethyl)phenyl 1.828 2-(n-Pentoxyimino-1'-ethyl)phenyl 1.829 3-(n-Pentoxyimino-1'-ethyl)phenyl 1.830 4-(n-Pentoxyimino-1'-ethyl)phenyl 1.831 2-(n-Hexoxyimino-1'-ethyl)phenyl 1.832 3-(n-Hexoxyimino-1'-ethyl)phenyl 1.833 4-(n-Hexoxyimino~ ethyl)phenyl 1.834 2-(Allyloxyimino-1'-ethyl)phenyl 1.835 3-(Allyloxyimino-1'-ethyl)phenyl 15 1.836 4-(Allyloxyimino-l'-ethyl)phenyl 1.837 2-(Benzyloxyimino-1'-ethyl)phenyl 1.838 3-(Benzyloxyimino-1'-ethyl)phenyl 1.839 4-(Benzyloxyimino-1'-ethyl)phenyl 20 1.840 2-(2-Fluorophenyl)phenyl 1.841 2-(2-Chlorophenyl)phenyl 1.842 2-(2-Methylphenyl)phenyl 1.843 2-(2-Methoxyphenyl)phenyl 25 1.844 4-~iso-~1v~v~y;minomethyl)phenyl 1.845 2-(n-Butoxyiminomethyl)phenyl 1.846 3-(n-Butoxyiminomethyl)phenyl 1.847 4-(n-Butoxyiminomethyl)phenyl 1.848 2-(i~o-Butoxyiminomethyl)phenyl 30 1.849 3-(iso-Butoxyiminomethyl)phenyl 1.850 4-(iso-Butoxyiminomethyl)phenyl 1.851 2-(tert-Butoxyiminomethyl)phenyl 1.852 3-(tert-Butoxyiminomethyl)phenyl 35 1.853 4-(tert-Butoxyiminomethyl)phenyl 1.854 2-(n-Pentoxyiminomethyl)phenyl 1.855 3-(n-Pentoxyiminomethyl)phenyl 1.856 4-(n-Pentoxyiminomethyl)phenyl 40 1.857 2-(n-Hexoxyiminomethyl)phenyl 1.858 3-(n-Hexoxyiminomethyl)phenyl 1.859 4-(n-Hexoxyiminomethyl)phenyl 1.860 2-(Allyloxyiminomethyl)phenyl 1.861 3-(Allyloxyiminomethyl)phenyl 1.862 4-(Allyloxyiminomethyl)phenyl 1.863 2-(Benzyloxyiminomethyl)phenyl 2199~22 Compound No. R2 1.864 3-(Benzyloxyiminomethyl)phenyl 1.865 4-(Benzyloxyiminomethyl)phenyl 5 1.866 2-(Methoxyimino-l'-ethyl)phenyl 1.867 3-(Methoxyimino-1'-ethyl)phenyl 1.868 4-(Methoxyimino-1'-ethyl)phenyl 1.869 3-Phenoxyphenyl 1.870 4-Phenoxyphenyl 1.871 2-Benzyloxyphenyl 1.872 3-BenzyloXyphenyl 1.873 4-Benzyloxyphenyl 1.874 4-(Imidazol-1'-yl)phenyl 15 1.875 4-(Piperazin-l'-yl)phenyl ( 1.876 4-(Morpholin-l'-yl)phenyl 1.877 4-(Piperidin-l'-yl)phenyl 1.878 4-(Pyridyl-2'-oxy)phenyl 20 1.879 2-Cyclopropylphenyl 1.880 3-Cyclopropylphenyl 1.881 4-Cycl~pLo~lphenyl 1.882 3-Cyclohexylphenyl 25 1.883 4-Cyclohexylphenyl 1.884 4-Oxiranylphenyl 1.885 6-F-pyrid-3-yl 1.886 6-C1-pyrid-3-yl 1.887 6-Br-pyrid-3-yl 30 1.888 6-CH3-pyrid-3-yl 1.889 6-CF3-pyrid-3-yl 1.890 6-CH3O-pyrid-3-yl 1.891 2-F-pyrid-4-yl 35 1.892 2-Cl-pyrid-4-yl 1.893 2-Br-pyrid-4-yl 1.894 2-CH3-pyrid-4-yl 1.895 2-CF3-pyrid-4-yl 40 1.896 2-CH30-pyrid-4-yl 1.897 3-F-pyrid-4-yl 1.898 3-Cl-pyrid-4-yl 1.899 3-Br-pyrid-4-yl 1.900 3-CH3-pyrid-4-yl 1.901 3-CF3-pyrid-4-yl 1.902 3-CH30-pyrid-3-yl 0050/45204 2 ~ g 9 1 2 2 C~."p~urld No. R2 1.903 5-F-pyrid-4-yl 1.904 S-Cl-pyrid-4-yl 5 1.905 5-Br-pyrid-4-yl 1.906 5-CH3-pyrid-4-yl 1.907 5-CF3-pyrid-4-yl 1.908 5-CH30-pyrid-4-yl 1.909 6-F-pyrid-4-yl 1.910 6-Cl-pyrid-4-yl 1.911 6-Br-pyrid-4-yl 1.912 6-CH3-pyrid-4-yl 1.913 6-CF3-pyrid-4-yl 15 1.914 6-CH30-pyrid-4-yl ( 1.915 2-F-pyrid-5-yl 1.916 2-Cl-pyrid-5-yl 1.917 2-Br-pyrid-S-yl 20 1.918 2-CH3-pyrid-5-yl 1.919 2-CF3-pyrid-5-yl 1.920 2-CH30-pyrid-5-yl 1.921 4-F-pyrid-5-yl 25 1.922 4-Cl-pyrid-5-yl 1.923 4-Br-pyrid-5-yl 1.924 4-CH3-pyrid-5-yl 1.925 4-CF3-pyrid-5-yl 1.926 4-CH30-pyrid-5-yl 30 1.927 3-F-pyrid-2-yl 1.928 3-Cl-pyrid-2-yl 1.929 3-Br-pyrid-2-yl 1.930 3-CH3-pyrid-2-yl 35 1.931 3-CF3-pyrid-2-yl 1.932 3-CH30-pyrid-2-yl 1.933 4-F-pyrid-2-yl 1.934 4-Br-pyr~d-2-yl 40 1.935 4-CF3-pyrid-2-yl 1.936 4-CH30-pyrid-2-yl 1.937 5-F-pyrid-2-yl 1.938 5-Cl-pyrid-2-yl 1.939 5-Br-pyrid-2-yl 1.940 5-CF3-pyrid-2-yl 1.941 5-CH3-pyrid-2-yl 2199~22 C~h~ d No. R2 1.942 5-CH30-pyrid-2-yl 1.943 6-F-pyrid-2-yl 5 1.944 6-Cl-pyrid-2-yl 1.945 6-Br-pyrid-2-yl 1.946 6-CH3-pyrid-2-yl 1.947 6-CF3-pyrid-2-yl 1.948 6-CH30-pyrid-2-yl 1.949 2-F-pyrid-3-yl 1.950 4-Cl-pyrid-2-yl 1.951 2-Br-pyrid-3-yl 1.952 2-CH3-pyrid-3-yl lS 1.953 2-CF3-pyrid-3-yl .1.954 2-CH30-pyrid-3-yl 1.955 4-F-pyrid-3-yl 1.956 4-Cl-pyrid-3-yl 20 1.957 4-Br-pyrid-3-yl 1.958 4-CH3-pyrid-3-yl 1.95g 4-CF3-pyrid-3-yl 1.960 4-CH30-pyrid-3-yl 25 1.961 S-F-pyrid-3-yl 1.962 S-Cl-pyrid-3-yl 1.963 S-~r-pyrid-3-yl 1.964 S-CH3-pyrid-3-yl 1.965 S-CF3-pyrid-3-yl 30 1.966 5-CH30-pyrid-3-yl 1.967 3-F-5-CF3-pyrid-2-yl 1.968 3,6-C12-S-CF3-pyrid-2-yl 1.969 6-C1-4-C~-pyrid-2-yl 35 1.970 3-CN-5-N02-pyrid-2-yl 1.971 2-Cl-6-F-pyrid-2-yl 1.972 6-Cl-4-F-pyrid-2-yl 1.973 4,6-F2-pyrid-2-yl 40 1.974 3,5-Cl2-6-F-pyrid-2-yl 1.975 6-CH30-3-N02-pyrid-2-yl 1.976 4-CN-6-F-pyrid-2-yl 1.977 6-C1-5-CN-pyrid-2-yl 1.978 6-C1-3-CN-pyrid-2-yl 1.979 6-C1-5-NO2-pyrid-2-yl 1.980 6-Cl-3-N02-pyrid-2-yl 0050/,5204 2 1 9 9 ~ 2 2 Compound No. R2 1.981 5-CN-6-F-pyrid-2-yl 1.982 3-CN-6-F-pyrid-2-yl 5 1.983 4,6-(CN)2-pyrid-2-yl 1.984 S-Br-4-CF3-pyrid-2-yl 1.985 3-N02-5-CF3-pyrid-2-yl 1.986 5-NH2-pyrid-2-yl 1.987 5-N02-pyrid-2-yl 1.988 4-CH3-5-N02-pyrid-2-yl 1.989 2,6-Cl2-pyrid-4-yl 1.990 5-(CH30C0)-pyrid-2-yl 1.991 5-Cl-6-F-pyrid-2-yl 15 1.992 S-Cl-6-011 pyLid-2-yl ( 1.993 S-C1-6-CH30-pyrid-2-yl 1.994 S-Cl-6-CN-pyrid-2-yl 1.995 5,6--C12--pyrid--2--yl 20 1.996 6-Br-5-Cl-pyrid-2-yl 1.997 5-Br-6-F-pyrid-2-yl 1.998 5-Br-6-Cl-pyrid-2-yl 1.999 S-Br-6-CN-pyrid-2-yl 25 1.1000 5-Br-6-OH-pyrid-2-yl 1.1001 5-Br-6-CH30-pyrid-2-yl 1.1002 4-cN-pyrid-2-yl 1.1003 6-CN-pyrid-2-yl 1.1004 S-Cl-pyrid-2-yl 30 1.1005 5-F-pyrid-2-yl ( 1.1006 5-CF3-1,3,4-Thiadiazol-2-yl 1.1007 4-Cl-1,2,5-Thiadiazol-3-yl 1.1008 4-Cl-Pyrimidin-2-yl 35 1.1009 4-Br-Pyrimidin-2-yl 1.1010 4-F-Pyrimidin-2-yl 1.1011 4-CH3-Pyrimidin-2-yl 1.1012 4-CH30-Pyrimidin-2-yl 40 1.1013 4-CH3CH20-Pyrimidin-2-yl 1.1014 4-N02-Pyrimidin-2-yl 1.1015 4-CN-Pyrimidin-2-yl 1.1016 4-CF3-Pyri~idin-2-yl 1.1017 4-C6H5-Pyrimidin-2-yl 1.1018 4-C6H50-Pyrimidin-2-yl 1.1019 5-F-Pyrimidin-2-yl 0050/45204 2 ~ 2 2 C~l..pol~nd No. R2 1.1020 5-CH3-Pyrimidin-2-yl 1.1021 5-CH30-Pyrimidin-2-yl 5 1.1022 5-CH3CH2O-Pyrimidin-2-yl 1.1023 5-NO2-Pyrimidin-2-yl 1.1024 5-CN-Pyrimidin-2-yl 1.1025 5-CF3-Pyrimidin-2-yl 1.1026 5-C6H5-Pyrimidin-2-yl 1.1027 5-C6H5O-Pyrimidin-2-yl 1.1028 4,5-Cl2-Pyrimidin-2-yl 1.1029 4,6-C12-Pyrimidin-2-yl 1.1030 4-Cl-5-CH30-Pyrimidin-2-yl 15 1.1031 2-F-Pyrimidin-4-yl (1.1032 2-Cl-Pyrimidin-4-yl 1.1033 2-F-Pyrimidin-4-yl 1.1034 2-~r-Pyrimidin-4-yl 20 1.1035 2-CH3-Pyrimidin-4-yl 1.1036 2-CH30-Pyrimidin-4-yl 1.1037 2-CH3CH2O-Pyrimidin-4-yl 1.1038 2-NO2-Pyrimidin-4-yl 25 1.1039 2-CH3S-Pyrimidin-4-yl 1.1040 2-Cyano-Pyrimidin-4-yl 1.1041 2-CF3-Pyrimidin-4-yl 1.1042 2-C6H5O-Pyrimidin-4-yl 1.1043 2-C6H5-Pyrimidin-4-yl 30 1.1044 6-NO2-Pyrimidin-4-yl 1.1045 6-Cyano-Pyrimidin-4-yl 1.1046 6-CF3-Pyrimidin-4-yl 1.1047 6-C6H50--Pyrimidin-4-yl 35 1.1048 6-C6H5-Pyrimidin-4-yl 1.1049 5-F-Pyrimidin-4-yl 1.1050 5-Cl-Pyrimidin-4-yl 1.1051 5-Br-Pyrimidin-4-yl 40 1.1052 5-CH3-Pyrimidin-4-yl 1.1053 5-CH30-Pyrimidin-4-yl 1.1054 5--CH3--CH20--Pyrimidin--4--yl 1.1055 5-NO2-Pyrimidin-4-yl 1.1056 5-Cyano-Pyri~idin-4-yl 1.1057 5-CF3-Pyrimidin-4-yl 1.1058 5-C6H5O-Pyrimidin-4-yl 2~99~22 C~L..~oulid No. R2 1.1059 5-C6H5-Pyrimidin-4-yl 1.1060 2-Cl-Pyrimidin-5-yl 5 1.1061 2-CH3-Pyrimidin-5-yl 1.1062 2-F-Pyrimidin-5-yl 1.1063 2-CH30-Pyrimidin-5-yl 1.1064 2-Cyano-Pyrimidin-S-yl 1.106~ 4-CH3-Pyrimidin-5-yl 1.1066 4-CH30-Pyrimidin-5-yl 1.1067 4-CF3-Pyrimidin-5-yl 1.1068 2,4-(CH3)2-Pyrimidin-5-yl 1.1069 2-CH3S-4-CH30-Pyrimidin-5-yl 15 1.1070 Pyrrol-2-yl-6-Cl-3-NO2-pyrid-2-yl 1.1071 6-Cl-3-NO2-pyrid-2-yl 1.1072 6-Cl-5-NO2-pyrid-2-yl 1.1073 3,6-(CH3)2-Pyrazin-2-yl 20 1.1074 6-F-Pyrimidin-4-yl 1.1075 6-Br-Pyrimidin-4-yl 1.1076 6-CH3-Pyrimidin-4-yl 1.1077 6-CH30-Pyrimidin-4-yl 25 1.1078 6-CH3CH2O-Pyrimidin-4-yl 1.1079 4,6-(CH3)2-Pyrimidin-2-yl 1.1080 2-CH3S-6-CH3-Pyrimidin-4-yl 1.1081 2-CH3S-Pyrimidin-4-yl 1.1082 4-C6H50-pyrid-2-yl 30 1.1083 5-C6H5O-pyrid-2-yl 1.1084 6-C6H5O-pyrid-2-yl 1.1085 6-Cl-pyrid-3-yl 1.1086 3,6-(CH3)2-pyrid-2-yl 35 1.1087 4,6-(CH3)2-pyrid-2-yl 1.1088 5,6-(CH3)2-pyrid-2-~l 1.1089 4-C6H5-6-CH3-pyrid-2-yl 1.1090 4,6-(C6H5)2-pyrid-2-yl 40 1.lo9l 3,4-Cl2-6-CH3-pyrid-2-yl 1.1092 3,4,5-Cl3_pyrid-2-yl 1.lOg3 3-CH3CO-4-CH3-pyrid-2-yl 1.1094 3-CH3CO-4,6-(CH3)-pyrid-2-yl 1.1095 3-CH30CO-pyrid-2-yl 1.1096 3-CH30CO-4-CH3-pyrid-2-yl 1.1097 3-CH3-4-Cl-pyrid-2-yl .
.
2 ~ 99422 Compound No. R2 1.1098 3-CH3-5-Cl-pyrid-2-yl 1.1099 3-CH3-6-Cl-pyrid-2-yl 5 1.1100 4-CH3-5-Cl-pyrid-2-yl 1.1101 4-CH3-6-Cl-pyrid-2-yl 1.1102 pyrid-2-yl 1.1103 pyrid-3-yl 1.1104 pyrid-4-yl 1.1105 pyrid-5-yl 1.1106 Pyrimidin-4-yl 1.1107 2-Cl-6-CH3-Pyrimidin-4-yl 1.1108 2,6-Di-Cl-Pyrimidin-4-yl 15 1.1109 2,5,6-Tri-Cl-Pyrimidin-4-yl 1.1110 2-Cl-Pyrimidin-4-yl 1.1111 2-CH3-Thiazol-4-yl 1.1112 1,2,4-Triazin-3-yl 20 1.1113 1,3,5-Triazin-2-yl 1.1114 Pyrazin-2-yl 1.1115 Quinolin-2-yl 1.1116 Quinolin-3-yl 25 1.1117 Pyridazin-3-yl 1.1118 6-Cl-Pyrazin-2-yl 1.1119 6-CH30-Pyrida2in-3-yl 1.1120 6-C1-4-CH3-Pyridazin-3-yl 1.1121 6-Cl-5-CH3-Pyridazin-3-yl 30 1.1122 1,3-Benzthiazol-2-yl (1.1123 Isoquinolin-1-yl 1.1124 Quinolin-4-yl 1.1125 6-Cl-Pyridazin-3-yl 35 1.1126 Pyridazin-4-yl 1.1127 Quinazolin-4-yl 1.1128 7-Cl-Quinolin-4-yl 1.1129 Purin-7-yl 40 1.1130 2-Cl-Purin-7-yl 1.1131 5-NOz-Thien-2-yl 1.1132 Thiazol-2-yl 1.1133 Thiazol-4-yl 1.1134 Thiazol-S-yl 1.1135 oxazol-2-yl 1.1136 Oxazol-4-yl oo~o/45204 2 I g ~ 1 2 2 Cor..~o~,d No. R2 1.1137 Oxazol-5-yl 1.1138 1,2,4-Triazin-5-yl 5 1.1139 1,2,4-Triazin-6-yl 1.1140 6-Cl-Pyrazin-2-yl 1.1141 6-Cl-Pyrazin-3-yl 1.1142 6-C1-Pyridazin-3-yl 1.1143 1,2,4-Triazol-1-yl 1.1144 1,2,3-Triazol-1-yl 1.1145 2-Cl-1~2~4-Oxadiazol-5-yl 1.1146 3-Cl-1, 2 ~ 4-Oxadiazol-S-yl 1.1147 Furan-2-yl 15 1.1148 N-CH3-Pyrrol-2-yl (~1.1149 3-CH3-Ql~;nol; n - 2 - yl 1.1150 4-CH3-Quinolin-2-yl 1.1151 4-C6H5-Quinolin-2-yl 20 1.1152 4-CH3CH2-Quinolin-2-yl 1.1153 6-Cl-Quinolin-2-yl 1.1154 8-CH3-Quinolin-2-yl 1.1155 8-Cl-Quinolin-2-yl 25 1.1156 3,4-(CH3)z-Quinolin-2-yl 1.1157 4-CH3-8-CH30-Quinolin-2-yl 1.1158 4-CH3-8-Cl-~uinolin-2-yl 1.1159 2-CH3-Quinolin-4-yl 1.1160 2-C1-Quinolin-4-yl 30 1.1161 Quinolin-8-yl ( 1.1162 2-CH3-Quinolin-8-yl 1.1163 2-Cl-Quinolin-8-yl 1.1164 2-CH3-6-C1-Quinolin-8-yl 35 1.1165 2-Thiophenyl 1.1166 3-Thiophenyl 1.1167 4-Cl-3-Thiophenyl 1.1168 2-Quinoxazinyl 40 1.1169 2-Furyl 1.1170 3-Furyl 1.1171 1-Pyrrolyl 1.1172 l-Imidazolyl 1.1173 Oxiranyl 1.1174 l-Azetidinyl 1.1175 1-Pyrrolidinyl .
OU50/452~4 ~ 2199 122 Compound No. RZ
1.1176 2-Tetrahydrofuryl 1.1177 2-TetrahydLop~Lanyl 5 1.1178 3-Tetrahydropyranyl 1.1179 l-Piperidinyl 1.1180 l-Morpholidinyl 1.1181 l-Piperazinyl 1.1182 1,3-Dioxan-2-yl 1.1183 CH3-C0 1.1184 CH3CH2-C0 1.1185 n-C3H7-C0 1.1186 iso-C3H7-C0 15 1.1187 n-C4Hg-CO
1.1188 ~ec-C4Hg-CO
1.1189 tert-C4Hg-CO
1.1190 iso-C4-Hg-CO
20 1.1191 CH30-C0 1.1192 CH3CH20-C0 1.1193 n-C3H~0-C0 1.1194 iso-C3H70-C0 25 1.1195 n-C4HgO-CO
1.1196 sec-C4HgO-CO
1.1197 tert-C4HgO-CO
1.1198 iso-C4HgO-CO
1.1199 Phenyl-C0 30 1.1200 2-Fluorophenyl-C0 1.1201 3-Fluorophenyl-C0 1.1202 4-Fluorophenyl-C0 1.1203 Pentafluorophenyl-C0 35 1.1204 2-Chlorophenyl-C0 1.1205 3-Chlorophenyl-C0 1.1206 4-Chlorophenyl-C0 1.1207 Pentachlorophenyl-C0 40 1.1208 2,3-Dichlorophenyl-C0 1.1209 2,4-Dichlorophenyl-C0 1.1210 2,5-Dichlorophenyl-C0 1.1211 2,6-Dichlorophenyl-C0 1.1212 3,4-Dichlorophenyl-C0 1.1213 3,5-Dichlorophenyl-C0 1.1214 2,3,4-Trichlorophenyl-C0 331 2~9~22 Compound No. R2 1.1215 2,3,5-Trichlorophenyl-C0 1.1216 2,3,6-Trichlorophenyl-C0 5 1.1217 2,4,5-Trichlorophenyl-C0 1.1218 2,4,6-Trichlorophenyl-C0 1.1219 3,4,5-Trichlorophenyl-C0 1.1220 2,3,4,6-Tetrachlorophenyl-C0 1.1221 2,3,5,6-Tetrachlorophenyl-Co 1.1222 2-Bromophenyl-C0 1.1223 3-Bromophenyl-C0 1.1224 4-Bromophenyl-C0 1.1225 2,4-Dibromophenyl-C0 lS 1.1226 3-~L._ - ~ fluorophenyl-C0 1.1227 3 - Bll_lc 4-methoxyphenyl-C0 1.1228 2-iodophenyl-C0 1.1229 3-iodophenyl-C0 20 1.1230 4-iodophenyl-C0 1.1231 2-Chloro-4-fluorophenyl-C0 1.1232 2-Chloro-5-fluorophenyl-C0 1.1233 2-Chloro-6-fluorophenyl-C0 25 1.1234 2-Chloro-4-bromophenyl-C0 1.1235 2-Bromo-4-chlorophenyl-C0 1.1236 2-Bromo-4-fluorophenyl-C0 1.1237 3-Bromo-4-chlorophenyl-C0 1.1238 3-Chloro-4-fluorophenyl-C0 30 1.1239 3-Fluoro-4-chlorophenyl-C0 1.1240 2-Cyanophenyl-C0 1.1241 3-Cyanophenyl-C0 1.1242 4-Cyanophenyl-C0 35 1.1243 2-Nitrophenyl-C0 1.1244 3-Nitrophenyl-C0 1.1245 4-Nitrophenyl-C0 1.1246 2-Methylphenyl-C0 40 1.1247 3-Methylphenyl-C0 1.1248 4-Methylphenyl-C0 1.1249 2,4-Dimethylphenyl-C0 1.1250 2,6-Dimethylphenyl-C0 1.1251 3,4-Dimethylphenyl-C0 1.1252 3,5-Dimethylphenyl-C0 1.1253 2,3,4-Trimethylphenyl-C0 Compound No. R2 1.1254 2,3,5-Trimethylphenyl- Co 1.1255 2,3,6-Trimethylphenyl-Co 5 1.1256 2,4,5-Trimethylphenyl-C0 1.1257 2,4,6-Trimethylphenyl-C0 1.1258 3,4,5-Trimethylphenyl-C0 1.1259 6-F-pyrid-3-yl-C0 1.1260 6-Cl-pyrid-3-yl-C0 1.1261 6-Br-pyrid-3-yl-C0 1.1262 6-CH3-pyrid-3-yl-C0 1.1263 6-CF3-pyrid-3-yl-C0 1.1264 6-CH30-pyrid-3-yl-C0 15 1.1265 2-F-pyrid-4-yl-C0 1.1266 2-Cl-pyrid-4-yl-C0 1.1267 2-Br-pyrid-4-yl-C0 1.1268 2-CH3-pyrid-4-yl-C0 20 1.1269 2-CF3-pyrid-4-yl-C0 1.1270 2-CH30-pyrid-4-yl-C0 1.1271 3-F-pyrid-4-yl-C0 1.1272 3-Cl-pyrid-4-yl-C0 25 1.1273 3-Br-pyrid-4-yl-C0 1.1274 3-CH3-pyrid-4-yl-C0 1.1275 3-CF3-pyrid-4-yl-C0 1.1276 3-CH30-pyrid-4-yl-C0 1.1277 5-F-pyrid-4-yl-C0 30 1.1278 5-Cl-pyrid-4-yl-C0 1.1279 5-Br-pyrid-4-yl-C0 1.1280 5-CH3-pyrid-4-yl-C0 1.1281 5-CF3-pyrid-4-yl-C0 35 1.1282 5-CH30-pyrid-4-yl-C0 1.1283 6-F-pyrid-4-yl-C0 1.1284 6-Cl-pyrid-yl-C0 1.1285 6-Br-pyrid-4-yl-C0 40 1-1286 6-CH3-pyrid-4- yl-CO
1.1287 6-CF3-pyrid-4-yl-C0 1.1288 6-CH30-pyrid-4-yl-C0 1.1289 2-F-pyrid-5-yl- CO
1.1290 2-Cl-pyrid-5-yl-C0 1.1291 2-Br-pyrid-5-yl-C0 1.1292 2-CH3-pyrid-5-yl-C0 CG...~v~d No. R2 1.1293 2-CF3-pyrid-5-yl-C0 1.1294 2-CH30-pyrid-5-yl-C0 5 1.1295 4-F-pyrid-5-yl-C0 1.1296 4-Cl-pyrid-5-yl-C0 1.1297 4-Br-pyrid-5-yl-C0 1.1298 4-CH3-pyrid-5-yl-C0 1.1299 4-CF3-pyrid-5-yl-C0 1.1300 4-CH30-pyrid-5-yl-C0 1.1301 3-F-pyrid-2-yl-C0 1.1302 3-Cl-pyrid-2-yl-C0 1.1303 3-Br-pyrid-2-yl-C0 15 1.1304 3-CH3-pyrid-2-yl-C0 1.1305 3-CF3-pyrid-2-yl-C0 1.1306 3-CH30-pyrid-2-yl-C0 1.1307 4-F-pyrid-2-yl-C0 20 1.1308 4-Br-pyrid-2-yl-C0 1.1309 4-CF3-pyrid-2-yl-C0 1.1310 4-CH30-pyrid-2-yl-C0 1.1311 5-F-pyrid-2-yl-C0 25 1.1312 5-Cl-pyrid-2-yl-C0 1.1313 5-Br-pyrid-2-yl-C0 1.1314 5-CF3-pyrid-2-yl-C0 1.1315 5-CH3-pyrid-2-yl-C0 1.1316 5-CH30-pyrid-2-yl-C0 30 1.1317 6-F-pyrid-2-yl-C0 (1.1318 6-Cl-pyrid-2-yl-C0 1.1319 6-Br-pyrid-2-yl-C0 1.1320 6-CH3-pyrid-2-yl-C0 35 1.1321 6-CF3-pyrid-2-yl-C0 1.1322 6-CH30-pyrid-2-yl-C0 1.1323 2-F-pyrid-3-yl-C0 1.1324 2-Cl-pyrid-3-yl-C0 40 1.1325 2-Br-pyrid-3-yl-C0 1.1326 2-CH3_pyrid-3-yl-C0 1.1327 2-CF3_pyrid-3-yl-C0 1.1328 2-CH30-pyrid-3-yl-C0 1.1329 4-F-pyrid-3-yl-C0 1.1330 4-Cl-pyrid-3-yl-C0 1.1331 4-Br-pyrid-3-yl-C0 2199~22 Co..lpound No. R2 1.1332 4-CH30-pyrid-3-yl-C0 1.1333 4-CF3-pyrid-3-yl-C0 5 1.1334 4-CH3-pyrid-3-yl-C0 1.1335 5-F-pyrid-3-yl C0 1.1336 5-C1-pyrid-3-yl-C0 1.1337 5-Br-pyrid-3-yl-C0 1.1338 5-CH3-pyrid-3-yl-C0 1.1339 S-CF3-pyrid-3-yl-C0 1.1340 5-CH30-pyrid-3-yl-C0 Table 1131 Compounds of the general formula I.F (n = 0) in which UR' i5 methoxy, VR" i~ methoxy and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a ~v...poulld corresponding to a group of Table L
~~ Table 1132 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methoxy and Af is the radical -N=CRgRh, Rg being methyl and Rh for a coll,~u~l,d corresponding to a group of Table L
Table 1133 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethoxy and Af i8 the radical -N=CRgRh, R9 being 30 methyl and Rh for a compound corresponding to a group of Table L
Table 1134 Compounds of the general formula I.F (n s 0) in which UR' iB
35 ethoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a cu.,.~ound corresponding to a group of Table L
Table 1135 40 Cv.,-pounds of the general formula I.F (n = 0) in which UR' i8 methylamino, VR" is methoxy and Af is the radical -N=cRsRh~ R9 being methyl and Rh for a compound corresponding to a group of Table L
ooso/45204 2 ~ 9 9 ~ 2 2 Table 1136 Com~o~l~ds of the general formula I.F (n = O ) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N-CRgRh, R9 5 being methyl and Rh for a compound co~responding to a group of Table L
Table 1137 10 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a compound corresponding to a group of Table L
15 Table 1138 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a compound corresponding to a group of Table L
Table 1139 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" i8 methylamino and Af is the radical -N=CR9Rh, R9 25 being methyl and Rh for a compound corresponding to a group of Table L
Table 1140 30 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a compound corresponding to a group of Table L
35 Table 1141 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a col,.poul,d corresponding to a group of 40 Table L
Table 1142 Compounds of the general formula I.F (n = 0) in which UR' is 45 ethoxy, VR is ethylamino and Af is the radical -N=CRgRh, Rg being methyl and Rh for a cG~.~pound corresponding to a group of Table L
-2199 12~
Table 1143 C~ o~nds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is methoxy and Af is the radical -N=CRgRh, Rg being 5 ethyl and Rh for a co~ o~I,d corresponding to a group of Table L
Table 1144 C~ ounds of the general formula I.F (n = 0) in which UR' is 10 ethoxy, VR" is methoxy and Af is the radical -NsCRgRh, Rg being ethyl and Rh for a ~vl.,p~und corresponding to a group of ~Table L
Table 1145 15 C~ ounds of the general formula I.F (n = 0) in which UR' i8 ! methoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a ~..,p~ d corresponding to a group of Table L
Table 1146 CGr~,~oul,ds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding t~ a group of Table L
25 Table 1147 C~ oullds of the general formula I.F (n 5 0) in which UR' is methyla~ino, VR" is methoxy and Af is the radical -N2CR9Rh, Rg being ethyl and Rh for a cvh.~Gund corresponding to a group of 30 Table L
Table 1148 Compounds of the general formula I.F (n s 0) in which UR' i8 35 ethylamino, VR~ is methoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1149 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, R9 being ethyl and Rh for a compound corresponding to a group of Table L
21g9~22 Table 1150 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being 5 ethyl and Rh for a compound corresponding to a group of Table L
Table 1151 Co...p~u~lds of the general formula I.F (n z 0) in which UR' is 10 methoxy, VR~' i8 methylamino and Af is the radical -N=CRgRh, R9 being ethyl and Rh for a c~ und corresponding to a group of Table L
Table 1152 ! Co.,.~vu~ds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1153 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 25 being ethyl and Rh for a cvm~oulld corresponding to a group of Table L
Table 1154 30 Compounds of the general formula I.F (n = 0) in which UR' i5 ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1155 Compounds of the general formula I.F tn = 0) in which UR' is methoxy, VR" is methoxy and Af is the radical -N~CRgRh, Rg being n-propyl and Rh for a c :EouLLd corresponding to a group of Table L
40 Table 1156 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VRn is methoxy and Af is the radical -N=CRgRh, Rq being n-propyl and Rh for a compound corresponding to a group of Table L
2199~22 ~able 1157 Compounds of the general formula I.F (n = 0) in which UR' iB
methoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being 5 n-propyl and Rh for a compound corresponding to a group of Table L
Table 1158 Co~.,poUnds of the general formula I.F (n = 0) in which UR' is 10 ethoxy, VRn is ethoxy and Af is the radical -N=CR9Rh, Rg being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1159 15 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VRn is methoxy and Af i5 the radical -N=CR9Rh, R9 being n-propyl and Rh for a ~ol~,kvund corresponding to a group of Table L
20 Table 1160 CG,..~unds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 being n-propyl and Rh for a compo~nd corresponding to a group of 25 Table L
Table 1161 Compounds of the general formula I.F (n = 0) in which UR' is 30 methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being n-propyl and Rh for a cv..,~ul.d corresponding to a group of Table L
Table 1162 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -~=CRgRh, R9 being n-propyl and Rh for a compound corresponding to a group of Table L
40 Table 1163 Compounds of the general f ormula I.F (n = 0) in which UR' i8 methoxy, VR" is methylamino and Af is the radical -N2CRgRh, R9 being n-propyl and Rh for a co",pound corresponding to a group of 45 Table L
2199~22 Table 1164 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rq 5 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1165 10 C~,ll~ou--ds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being n-propyl and Rh for a c~ ound corresponding to a group of Table L
15 Table 1166 ~' Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, R9 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1167 Compounds of the general formula I.F (n = 0) in which UR' i5 methoxy, VR" is methoxy and Af is the radical -N=CR9Rh, R9 being 25 cyclopropyl and Rh for a c~lupound correspo~ng to a group of Table L
Table 1168 30 Compounds of the general formula I.F (n ~ 0) in which UR' i~
ethoxy, VR" is methoxy and Af is the radical -N=CR9Rh, Rg being cyclopropyl and Rh for a compound corresponding to a group of Table L
35 Table 1169 Compounds of the general formula I.F (n e o) in ~hich UR' is methoxy, VR" is ethoxy and Af is the radical -NsCR9Rh, Rg being cyclopropyl and Rh for a cG..*ound corresponding to a group of 40 Table L
-2Ig9!!22 Table 1170 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being S cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1171 10 Compounds of the general formula I.F (n - 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 being cyclopropyl and Rh for a c~ _ound corresponding to a group of Table L
15 Table 1172 ¢
Compounds o~ the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af i8 the radical -N=CRgRh, Rg being cyclopropyl and Rh for a c~ -und corresponding to a group 20 of Table L
Table 1173 Compounds of the general formula I.F (n = 0) in which UR' is 25 methylamino, VR" is ethoxy and Af i8 the radical -N=CR9Rh, Rg being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1174 CG..*o~nds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af iS the radical -N=CR9Rh, R9 being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1175 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VRn is methylamino and Af is the radical -N=CRgRh, R9 40 being cyclopropyl and Rh for a compound corresponding to a group of Table L
0050t45204 2199~22 Table 1176 Compounds of the general formula I.F (n = 0) in which UR' i5 ethoxy, VRn is methylamino and Af is the radical -N=CRgRh, Rg 5 being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1177 10 Compounds of the general formula I.F (n = 0) in which UR' i8 methoxy, VR" i8 ethylamino and Af is the radical -N=CRgRh, Rg being cyclopropyl and Rh for a cG...~ouild corresponding to a group of Table L
15 Table 1178 ( Cv...pounds of the general formula I.F (n = 0) in which UR' i8 ethoxy, VRn is ethylamino and Af is the radical -N=CRgRh, Rg being cyclopropyl and Rh for a compound corresponding to a group of 20 Table L
Table 1179 Compounds of the general formula I.F (n = 0) in which UR' is 25 methoxy, VRn is methoxy and Af is the radical -N=CRqRh, Rg being CF3 and Rh for a cGm~o~nd corresponding to a group of Table L
Table 1180 30 co.,~u"ds of the general formula I.F (n = 0) in which UR' i8 ethoxy, VR" is methoxy and Af is the radical -N-CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
Table 1181 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR~ is ethoxy and Af is the radical -N=C~RgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
40 Table 1182 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR~' is ethoxy and Af is the radical -N=CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
-~able 1183 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, Rg 5 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1184 10 Compounds of the general formula I~F (n = 0) in which UR' is ethylamino, VR" i8 methoxy and Af is the radical -N=CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
15 Table 1185 ( Compounds of the general formula I.F (n 3 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being CF3 and Rh for a compound corresponding to a group of Table Table 1186 Compounds of the general formula I.F (n z 0) in which UR' is 25 ethylamino, VR" is ethoxy and Af is the radical -N=CRgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1187 30 Compounds of the general formula I.F (n = 0) in which UR' i~
methoxy, VR" is methylamino and Af is the radical -N=cRsRh~ Rs being CF3 and Rh for a compound corresponding to a group of Table L
35 Table 1188 Compounds of the general formula I.F (n = o) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table ~ 2199~22 Table 1189 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 5 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1190 10 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CR9Rh~ Rg being CF3 and Rh for a compound corrQsponding to a group o~ Table L
Table 1191 Co,-,~ou~-ds of the general formula I.F (n = 0) in which UR' is methoxy, VRn is methoxy and Af i8 the radical -N=CRgRh, Rg being methylthio and Rh for a co...~Gulld corresponding to a group of Table L
~ 20 Table 1192 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methoxy and Af i~ the radical -N=CR9Rh, Rg being 25 methylthio and Rh for a cv~ ound corresponding to a group of Table L
Table 1193 30 Compound~ of the general formula I.F (n = 0) in which UR' is f methoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rs being ~ methylthio and Rh for a compound corresponding to a group of Table L
35 Table 1194 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, R9 being methylthio and Rh for a cv...~Gul~d corresponding to a group of Table .
21g9~2 Table 1195 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 5 being methylthio and Rh for a compound corresponding to a group of Table L
Table 1196 10 C~."~ounds of the general formula I.F (n - 0) in which UR' is ethylamino, VR" is methoxy and Af i5 the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
15 Table 1197 ( Compounds of the general formula I.F (n 2 o) in which UR' is methylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, Rg being methylthio and Rh ~or a c po~nd corresponding to a group of 20 Table L
Table 1198 Compounds of the general formula I.F (n - 0) in which UR' i5 25 ethylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
Table 1199 C~...pouilds of the general formula I.F (n S 0) in which UR~ is methoxy, VRn is methylamino and Af is the radical -N=CR9Rh, R9 being methylthio and Rh for a compound corresponding to a group of Table L
Table 1200 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methylamino and Af is the radical -NsCRgRh, R9 40 being methylthio and Rh for a compound corresponding to a group of Table L
.
2I9g422 3g5 Table 1201 Compounds of the general formula I.F (n ~ 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 5 being methylthio and Rh for a cull*oul,d corresponding to a group of Table L
Table 1202 10 CG..~ounds of the general formula I.F (n - 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
15 Table 1203 Compounds of the general formula I.F (n = 0) in which UR' i8 methoxy, VR" is methoxy and Af i8 the radical -N-CRgRh, R9 being cyano and Rh for a c~l"~ound corresponding to a group of Table L
Table 1204 Compounds of the general formula I.F ~n - 0) in which UR' i8 ethoxy, VR" i8 methoxy and Af is the radical -N=CR9Rh, R9 being 25 cyano and Rh for a c~.,.~ound corresponding to a group of Table L
Table 1205 Compounds of the general formula I.F (n = 0) in which UR' is 30 methoxy, VR~' is ethoxy and Af is the radical -N=CR9Rh, R9 being cyano and Rh for a co,-.pound corresponding to a group of Table L
Table 1206 35 Co~ o~L.ds of the general formula I.F (n 5 O) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -NsCR9Rh, Rq being cyano and Rh for a co,ll~oul-d corresponding to a g~oup of Table L
Table 1207 C~,..pounds of the general formula I.F (n = 0) in which UR' i8 methylamino, VR" is methoxy and Af is the radical -N=CRgRh, Rg being cyano and Rh for a c~ _ und corresponding to a group of Table L
2199~22 Table 1208 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 5 being cyano and Rh for a compound corresponding to a group of Table L
Table 1209 10 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being cyano and Rh for a compound corresponding to a group of Table L
15 Table 1210 ( Co,-.~oUnds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CR~Rh, Rg being cyano and Rh for a cv..~oulld corresponding to a group of Table Table 1211 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rg 25 being cyano and Rh for a ~v.ll~ound corresponding to a group of Table L
Table 1212 30 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and A~ is the radical -N=CR9Rh, R9 ~~ being cyano and Rh for a co,llpound corresponding to a group of Table L
35 Table 1213 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, Rg being cyano and Rh for a compound corresponding to a group of 40 Table L
Table 1214 Compounds of the general formula I.F (n = 0) in which UR~ is 45 ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being cyano and Rh for a compound corresponding to a group of Table L
~199~22 Table L
No. Rh C6Hs 5 2 2-Cl-C6H4 3 3-Cl-C6H4 4 4-Cl-C6H4 2,4-Clz-C6H3 10 6 2,5-Clz-C6H3 7 2,6-Cl2-C6H3 8 3,4-C12-C6H3 9 2-Br-C6H4 3-Br-C6H4 15 11 4-~r-C6H4 18 2,4-~CH3)2-C6H3 25 19 2,5-(CH3)2-C6H3 2,6-(CH3)2-C6H3 21 3,4-(CH3)2-C6H3 22 2-CH(CH3)2-C6H4 30 23 3-CH(CH3)z-C6H4 24 4-CH(CH3)2-C6H4 ( 25 2-c(cH3)3-c6H4 26 3-C(CH3)3-C6H4 27 4-C(CH3)3-C6H4 35 28 3-CH3, 4-C(CH3)3-C6H3 29 4-CH3, 3-C(CH3)3-C6H3 33 2-OCH(CH3)z-C6H4 34 3-OCH(CH3)2-C6H4 4-OCH(CH3)z~C6H4 45 36 2-OC(CH3)3-C6H4 37 3-OC(CH3)3-C6H4 38 4-OC(CH3)3-C6H4 2~99 122 No. Rh 43 3-ocF3-C6H4 44 - 4-oCF3-C6H4 2-sc(cH3)3-c6H4 46 3-SC(CH3)3-C6H4 47 4-sc(cH3)3-C6H4 51 3-C(CH3)2NOCH3-C6H4 52 4-C(CH3)=NOCH3-C6H4 53 2-CH3, 4-C(CH3)2NOCH3-C6H3 20 54 2,5-(CH3)2, 4-C(CH3)=NOCH3-C6Hz 2-CH3, 5-Cl-C6H3 56 5-CH3, 2-Cl-C6H3 57 2,3,4-C13-C6H2 3,4,5-C13-C6H2 62 CH(cH3) 2 63 C(CH3)2-O-CH3 64 C(CH3)z-O-CH2CH3 Cyclopropyl 66 Cyclopentyl 35 67 Cyclohexyl 68 l-Naphthyl 69 2-Naphthyl 2-Pyridyl 40 71 3-Pyridyl 72 4-Pyridyl 73 2-Thienyl 74 3-Thienyl 45 75 5-Cl-Thien-2-yl 76 5-Cl-Thien-3-yl 77 2-Furyl 2I 99~ 22 No. Rh 78 3-Furyl 79 2-Pyrimidinyl 5 80 4-Pyrimidinyl 81 5-Pyrimidinyl 82 4-OC2H5-pyrimidin-2-yl 83 2-Pyrazinyl Table 1215 CG".~o~,lds of the general formula I.G (n = 0) in which UR' is methoxy, VR" is methoxy, Y9 is oxygen and A9 for a compound 15 corresponds to a group of Table M
Table 1216 Compounds of the general formula I.G (n a O) in which UR' i8 20 ethoxy, VR" is methoxy, Yg is oxygen and Ag for a co...~ound corresponds to a group of Table M
Table 1217 25 C ~ounds of the general formula I.G (n 8 O) in which UR' is methoxy, VR" is eth~xy, Yg is oxygen and Ag for a compound corresponds to a group of Table M
Table 1218 ' Compounds of the general formula I.G (n = 0) in which UR' is ethoxy, VRN is ethoxy, Y9 is oxygen and A9 for a cor..~ound corresponds to a group of Table M
35 Table 1219 Cor..pounds of the general formula I.G (n = 0) in ~hich UR' i5 methylamino, VR~' is methoxy, Yg is oxygen and Ag for a cGr..~und corresponds to a group of Table M
Table 1220 ~
Compounds of the general formula I.G (n = 0) in which UR' is ethylamino, VR~' is methoxy, Yg is oxygen and A9 for a ~on,~oul-d 45 corresponds to a group of Table M
~ 2199~22 Table 1221 Compounds of the general formula I.G (n = 0) in which UR' is methylamino, VRn iS ethoxy, Yg is oxygen and A9 for a cv.,.~o~lld 5 corresponds to a group of Table M
Table 1222 Compounds of the general formula I.G (n - 0) in wh~ch UR' is 10 ethylamino, VRn i8 ethoxy, Y9 is oxygen and Ag for a compound corresponds to a group of Table M
Table 1223 15 Co...pounds of the general formula I.G ~n = 0) in which UR' is methoxy, VR" is methylamino, Y9 is oxygen and Ag for a co...poul.d corresponds to a group of Table M
Table 1224 Compounds of the general formula I.G ~n = 0) in which UR' is ethoxy, VRn is methylamino, Yg is oxygen and Ag for a compound corresponds to a group of Table M
25 Table 1225 Compounds of the general formula I.G (n = 0) in which UR' is methoxy, VRn iS ethylamino, Yg i8 oxygen and Ag for a compound corresponds to a group of Table M
Table 1226 C unds of the general formula I.G (n = 0) in which UR' is ethoxy, VR" i8 ethylamino, Yg is oxygen and Ag for a ~ v~nd 35 corresponds to a group of Table M
Table M .
No. Ag 40 1 C6Hs 2 2-Cl-C6H4 3 3-Cl-C6H4 4 4-Cl-C6H4 45 5 2,4-Cl2-C6H3 6 2,5-Cl2-C6H3 7 2,6-Cl2-C6H3 -0050~45~04 ~ 351 2199~22 No. . Ag 8 3,4-Cl2-c6H3 12 2,4-(CH3)2-C6H3 13 2,5-(CH3)2-C6H3 2,6-(CH3)2-C6H3 3,4-(CH3)2-C6H3 16 2-Cl, 5-CH3-C6H3 17 5-Cl, 2-CH3-C6H3 3-oC6Hs~C6H4 26 4-oC6H5-C6H4 ( 33 4-Br, 3-CF3-C6H3 34 4-Cl, 3-OCH3-C6H3 3~4-~OCHzO]-C6H3 36 2-cl, 3,4-tOCH2O]-C6H2 0 40 CH(cH3)2 41 CH2cH2cH2cH3 42 CH(CH3)CH2CH3 43 CH2CH(CH3) 2 44 C(CH3)3 46 Cyclopropyl 0050~45204 Z199~22 No. Ag 47 Cyclopentyl ~ 48 Cyclohexyl 49 CH=CHCH3 C-C-C(CH3)3 51 1-Naphthyl 52 2-Naphthyl 53 2-CH3-thiazol-4-yl 54 2-CH(CH3)2-thiazol-4-yl 2-CF3-thiazol-4-yl 56 2-OCH3-thiazol-4-yl 57 2-SCH3-thiazol-4-yl 15 58 2-NHCH3-thiazol-4-yl ( 59 2-N~CH3)2-thiazol-4-yl 2-C6H5-thiazol-4-yl 61 2-(4-OCF3-C6H4)-thiazol-4-yl 20 62 C6Hs-C(sO) 63 2-Cl-C6H4-C(=O) 64 3-Cl-C6H4-C(=O) 4-Cl-C6H4-C(=O) 25 66 2,4-Cl2-C6H3-C(=o) 67 2,5-Cl2-C6H3-C(=O) 68 2,6-Cl2-C6H3-C(=O) 69 3,4-Cl2-C6H3-C(=O) 2-CH3-C6H4-C(=O) 30 71 3-CH3-C6H4-C(=O) ( 72 4-CH3-C6H4-C(=O) 73 2,4-(CH3)2-C6H3-C(=O) 74 2,5-(CH3)2-C6H3-C(=O) 35 75 2,6-(CH3)2-C6H3-c(=O) 76 3,4-(CH3)2-C6H3-C(=O) 77 2-Cl, 5-CH3-C6H3-C(=O) 78 5-Cl, 2-CH3-C6H3-C(=O) 40 79 2-OCH3-C6H4-C(=O) 8 0 3--OCH3--C6H4--C ( =O ) 81 4-OCH3-C6H4-C(sO) 82 2-C6Hs~C6H4~c(sO) 45 83 3-C6Hs-c6H4-c(=O) 84 4-C6H5-C6H4-C(=O) 2-OC6H5-C6H4-C(=o) _ ~ 9422 No. A9 86 3-OC6H5-C6H4-C(=O) 87 4-OC6Hs-C6H4-C( 20 ) 5 88 2-Noz-c6H4-c(=o) 89 3-NO2-C6H4-C( 80 ) g o 4--~o2-c6H4--c ( =o ) 91 2-CN-C6H4-C(=O) 10 92 3-CN-C6H4-C(=O) 93 4-CN-C6H4-C(=O) 94 4-Br, 3-CF3-C6H3-C(-O) 9S 4-Cl, 3-OCH3-C6H3-C~-O) 96 C6H5-CH(OH)-15 97 2-Cl-C6H4-CH(OH)-98 3-Cl-C6H4-CH(OH)-99 4-Cl-C6H4-CH(OH)-100 2,4-Cl2-C6H3-CH(OH)-20 101 2,5-Cl2-C6H3-CH~OH)-102 2,6-Cl2-C6H3-CH(OH)-103 3,4-Clz-C6H3-CH(OH)-104 2-CH3-C6H4-CH(OH)-25 105 3-CH3-C6H4-CH(OH)-106 4-CH3-C6H4-CH(OH)-107 2,4-(CH3)z-C6H3-CH(OH)-108 2~5-(cH3)2-c6H3-cH(oH)-109 2,6--(CH3)z--C6H3--CH(OH)--110 3,4-(CH3)2--C6H3--CH(OH)--111 2-Cl, 5-CH3-C6H3-CH(OH)-112 5-Cl, 2-CH3-C6H3-~H(OH)-113 2-OCH3-C6H4-CH(OH)-35 114 3-OCH3-C6H4-CH(OH)-115 4-OCH3-C6H4-CH(OH)-116 2-C6H5-C6H4-CH(OH)-117 3-C6Hs-C6H4-CH(OH)-40 118 4-C6H5-C6H4-CH(OH)-119 2-OC6H5-C6H4-CH(OH)-120 3-OC6HS-C6H4-CH(OH)-121 4-OC6H5-C6H4-CH(OH)-45 122 2-NO2-C6H4-CH(OH)-123 3-NO2-C6H4-CH(OH)-124 4-N02-C6H4-CH(OH)-2199~22 No. A9 125 2-CN-C6H4-CH(OH)-126 3-CN-C6H4-CH(OH)-5 127 4-CN-C6H4-CH(OH)-128 4-Br, 3-CF3-C6H3-CH(OH)-129 4-Cl, 3-OCH3-C6H3-CH(OH)-10 Table 1227 Compounds of the ~eneral formula I.H (n - m 8 ~) ~n which UR' is methoxy, VR" i~ methoxy and Ah for a compound corresponds to a group of Table N
Table 1228 Compounds of the general formula I.H (n = m ~ O) in which UR' is ethoxy, VR" is methoxy and Ah for a cv~ ound corresponds to a 20 group of Table N
Table 1229 Compounds of the general formula I.H (n = m = O) in which UR' is 25 methoxy, VRn is ethoxy and Ah for a oo-"~ound corresponds to a group of Table N
Table 1230 30 Compounds of the general formula I.H (n - m = O) in which UR' is ethoxy, VR" is ethoxy and Ah for a ~",~ound corresponds to a group of Table N
Table 1231 Compounds of the general formula I.H (n = m = O) in which UR' is methylamino, VR" is methoxy and Ah for a compound corresponds to a group of Table N
40 Table 1232 Compounds of the general formula I.H (n = m = O) in which UR' is ethylamino, VR" is methoxy and Ah for a c~ ound corresponds to a group of Table N
U(15~ !lJ4 355 2 1 9 9 ~ 2 2 Table 1233 . .
Co...~ou,lds of the general formula I.H (n = m = 0) in which UR' is methylamino, VR" is ethoxy and Ah for a compound corresponds to a 5 group of Table N
Table 1234 Compounds of the general formula I.H (n = m = 0) in which UR' is 10 ethylamino, VR" is ethoxy and Ah for a co,..pound corresponds to a group of Table N
Table 1235 15 C _ unds o~ the general formula I.H (n - m = 0) in which UR' i8 methoxy, VR" is methylamino and Ah for a compound corresponds to a group of Table N
Table 1236 ~ 20 Compounds of the general formula I.H (n = m = 0) in which UR' is ethoxy, VR" is methylamino and Ah for a compound corresponds to a group of Table N
25 Table 1237 Compounds of the general formula I.H (n = m = 0) in which UR' is methoxy, VR" is ethylamino and Ah for a compound correspond~ to a group of Table N
Table 1238 Compounds of the general formula I.H (n = m = 0) in which UR' is ethoxy, VR~ is ethylamino and Ah for a compound corresponds to a 35 group of Table N
Table N
No. Ah 40 1 Br 2~9~22 No. Ah 9 C ( CH3 ) =NOCH3 12 CO2C(CH3)3 C--C-C(CH3)3 16 C----C-Si(CH3)3 2 0 C6H5--OcH2 24 2-F--C6H4-cH2o 2 6 2-F--C6H4--CH=CH--2 7 2--F--C6H4-C _ C--3 o 3-F--C6H4--OcH2 31 3--F--C6H4--CH=CH--3 5 4-F-C6H4--OcH2 38 2-Cl--C6H4 3 9 2--Cl--C6H4--cH2o 2--Cl--C6H4--ocH2 41 2-Cl--C6H4--CH=CH--4 2 2-Cl--C6H4-C = C--43 3-Cl--C6H4 44 3-Cl--C6H4--cH2o 3-Cl--c6H4-ocH2 4 6 3-Cl--C6H4-CH=CH--~199122 No. . Ah 47 3-Cl-C6H4-C 8 C-4B 4-Cl-C6H4 5 49 4-cl-c6H4-cH2o 4-cl-c6H4-ocH2 51 4-Cl-C6H4-CH=CH-52 4-Cl-C6H4-CoC~
2,4-Cl2-C6H3 54 2,4-Cl2-C6H3-CH20 2,4-cl2-c6H3-ocH2 56 2,4-Cl2-C6H3-CH=CH-57 2,4-Cl2-C6H3-C-C-15 58 2,5-Cl2-C6H3 59 2,5-cl2-c6H3-cH2o 2,5-cl2-c6H3-ocH2 61 2,5-Cl2-C6H3-CH=CH-20 62 2,5-Cl2-C6H3-C8C-63 2,6-Cl2-C6H3 64 2,6-cl2-c6H3-cH2o 2,6-C12-C6H3-0CH2 25 66 2,6-Cl2-C6H3-CH=CH-67 2,6-Cl2-C6H3-C 8C -68 3,4-Cl2-C6H3 69 3,4-Cl2-C6H3-CH20 3,4-Cl2-C6H3-0CH2 71 3,4-Cl2-C6H3-CH=CH-72 3,4-Cl2-C6H3-C8C-76 2-CH3-C6H4-CH=CH-81 3-CH3-C6H4-CH=CH-- -v v ~ u ~
2199~22 No. Ah 86 4-CH3-C6H4-CH=CH-5 88 2,4-(CH3)2-C6H3 89 2,4-(CH3)2-C6H3-CH2O
go 2,4-(CH3)2-C6H3-OCH2 91 2,4-(CH3)2-C6H3-CH=CH-lO 92 2,4-(CH3)2-C6H3-C-C-93 2,5-(CH3)2-C6H3 94 2,5-(CH3)2-C6H3-CH20 2,5-(CH3)2-C6H3-0CH2 96 2,5-(CH3)2-C6H3-CH=CH-97 2,5-(CH3)2-C6H3-C-C-98 2,6-(CH3)2-C6H3 99 2,6-(CH3)2-C6H3-CH20 100 2,6-~CH3)2-C6H3-0cH2 20 101 2,6-(CH3)2-C6H3-CH=CH-102 2,6-(CH3)2-C6H3-C-C-103 3,4-(CH3)2-C6H3 104 3~4-(CH3)2-c6H3-cH20 25 105 3,4-(CH3)2-C6H3-OCH2 106 3,4-(CH3)2-C6H3-CH=CH-107 3,4-(CH3)2-C6H3-C-C-108 2-CH3, 5-Cl-C6H3 109 2-CH3, 5-Cl-C6H3-CH2O
30 110 2-CH3, 5-Cl-C6H3-OCH2 111 2-CH3, 5-Cl-C6H3-CH=CH-112 2-CH3, 5-Cl-C6H3-CaC-113 5-CH3, 2-Cl-C6H3 35 114 5-CH3, 2-Cl-c6H3-cH2O
115 5-CH3, 2-cl-c6H3-ocH2 -116 5-CH3, 2-Cl-C6H3-CH=CH-117 5-CH3, 2-cl-C6H3-CaC-124 3-OCH3-C6H4-cH2O
0050/45204 2 ~ 9 9 ~ 2 2 35g No. Ah 125 3-OCH3-C6H4-OCHz 126 3-OCH3-C6H4-CH=CH-5 127 3-OCH3-C6H4-C_C-129 4-OCH3-C6H4-cH20 130 4-OCH3-C6H4-0cH2 10 131 4-OCH3-C6H4-CH=CH-134 2-CN-C6H4-cH20 135 2-CN-C6H4-0cH2 15 136 2-CN-C6H4-CH=CH-137 2-CN-C6H4-C_C-139 3-CN-C6H4-cH20 141 3-CN-C6H4-CH=CH-142 3-CN-C6H4-CaC-25 144 4-CN-C6H4-cH20 146 4-CN-C6H4-CH=CH-147 4-CN-C6H4-C_C-148 4-oc6H4-C6H4 149 4-OC6H4-C6H4-cH20 ~=
f'150 4--OC6H4--C6H4--OCH2 151 4-OC6H4-C6H4-CH=CH-152 4-OC6H~-C6H4-C=C-35 153 2-Pyridyl lS4 3-Pyridyl 155 4-Pyridyl 156 4-Pyridyl-C-C-40 157 2-Pyrimidyl 158 4-Pyrimidyl 159 5-Pyrimidyl 160 2-Thienyl 45 161 3-Thienyl 162 5-Cl-2-thienyl 163 2-Furyl -~U5U/ 4S~4 2199~22 No. Ah 164 3-Furyl 165 2-Thiazolyl 5 166 4-Thiazolyl 167 2-CH3-thiazol-4-yl 16B 2-CH~CH3)2-thiazol-4-yl 169 2-C~CH3)3-thiazol-4-yl 10 170 2-OCH3-thiazol-4-yl 171 2-CF3-thiazol-4-yl 172 2-SCH3-thiazol-4-yl 173 2-N(CH3)2-thiazol-4-yl 174 2-C6H5-thiazol-4-yl 15 175 2-(4-F-C6H4)-thiazol-4-yl 176 2-(4-CH3-C6H4)-thiazol-4-yl 177 2-(4-CF3-C6H4)'-thiazol-4-yl 178 2-(4-ocH3-c6H4)-thiazol-4 20 179 2-(4-OCF3-C6H4)-thiazol-4-yl 180 2-~3,4-(OCH20)-C6H3]-thiazol-4-yl 181 2-S(=O)CH3-thiazol-4-yl 182 2-t2-CH2CH3-thiazol-4-yl]-thiazol-4-yl 25 183 2-[2-CH(CH3)z-thiazol-4-yl]-thiazol-4-yl 184 2-[2-C(CH3)3-thiazol-4-yl]-~ h; A 7~1 - 4-yl 185 5-NO2-thiazol-2-yl 186 4-~4-F-C6H4), 5-CH3-thiazol-2-yl 187 Isoxazol-5-yl 30 188 3-CH3-isoxazol-5-yl 189 3-CH(CH3)2-isoxazol-5-yl 190 3-C(CH3)3-isoxazol-5-yl 191 3-(CH2)4CH3-isoxa201-5-yl 35 192 3-[CH(CH3)CH2CH2CH3]-isoxazol-5-yl 193 3-CF3-isoxazol-5-yl 194 3-OCH3-isoxazol-5-yl .
195 3-C6H5-isoxazol-5-yl 40 196 3-(4-F-C6H4)-isoxa201-5-yl 197 3-(3~4-Cl2-C6H3)-isoxazol-5-yl 198 3-(4-CH3-C6H4)-isoxazol-5-yl 199 3-(4-CF3-C6H4)-isoxazol-5-yl 45 200 3-(4-OCH3-C6H4)-isoxazol-5-yl 201 3-(4-OCF3-C6H4)-isoxazol-5-yl 202 5-CH3-1,2,4-oxadiazol-3-yl 0050~45204 2~99~22 No. Ah 203 5-CF3-1,2,4-oxadiazol-3-yl 204 5-CH3-1,3,4-thiadiazol-2-yl 5 205 5-CF3-1,3,4-thiadiazol-2-yl Table 1239 Compounds of the general formula I.K (n = 0) in which UR' is 10 methoxy, VRn is methoxy, Rf is hydrogen and the combination of the substituents R~, Rd and Ak corresponds for each co...~ouid to a line of Table 0 Table 1240 Ccr..~uul,ds of the general for~t-l~ I.K (n = 0) in which UR' is ethoxy, VR~ i8 methoxy, Rf is hydrogen and the combination of the substituents Re~ Rd and Ak corresponds for each cv...~ound to a line of Table 0 Table 1241 Compounds of the general formula I.K (n = 0) in which UR' is methoxy, VR" is ethoxy, Rf is hydrogen and the comh~n~tion of the 25 substituents Re, Rd and Ak corresponds for each c~ und to a line of Table 0 Table 1242 30 Compounds of the general formula I.K (n = 0) in which UR' is . ethoxy, VR" is ethoxy, Rf is hydrogen and the combination of the f substituents R~, Rd and Ak corresponds for each c~ ound to a line of Table 0 35 Table 1243 Compounds of the general formula I.K (n = 0) in wh~ch UR' is methylamino, VRn is methoxy, Rf is hydrogen and the combination of the substituents Re, Rd and Ak corresponds for each compound to a 40 line of Table o ~JU3U~ ~v~
~ 2199~22 Table 1244 Compounds of the general formula I.K (n - 0) in which UR' is ethylamino, VR" is methoxy, Rf is hydrogen and the c~mh;n~tion of 5 the substituents Rer Rd and Ak corresponds for each compound to a line of Table 0 Table 1245 10 Cvm~oullds of the general formula I.K (n = 0) in which UR' is methylamino, VRn is ethoxy, Rf is hydrogen and the combination of the substituents R~, Rd and Ak correspond~ ~or each cor.~und to a line of Table o 15 Table 1246 ( Compounds of the general formula I.K (n = 0) in which UR' is ethylamino, VR" is ethoxy, Rf is hydrogen and the combination of the substituents RQ, Rd and Ak corresponds for each co,l.pound to a 20 line o~ Table 0 Table 1247 Co..,~v~nds of the general formula I.K (n = 0) in which UR' is 25 methoxy, VR" is methylamino, Rf i5 hydrogen and the combination of the substituents Re~ Rd and Ak corresponds for each compound to a line of Table 0 Table 1248 Compounds of the general formula I.K (n = 0) in which UR' ls ethoxy, VR" is methylamino, Rf is hydrogen and the c~h; n~tion of the substituents Re~ Rd and Ak corresponds for each ~G..I~ound to a line of Table 0 Table 1249 Compounds of the general formula I.K (n = 0) in~which UR' is methoxy, VR" is ethylamino, Rf is hydrogen and the combination of 40 the substituents Re~ Rd and Ak corresponds for each com~ound to a line of Table 0 = ~ ~
2199~22 Table 1250 Compounds of the general f ormula I.R (n = 0) in which UR' is ethoxy, VR" is ethylamino, Rf is hydrogen and the combination of 5 the substituents Re~ Rd and Ak corresponds for each compo~nd to a line of Table O
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No. Re Rd Ak O
179 CH3 CH3 3~4-(OCH3) ff 6H3-cH2 ~
180 CH3 CH3 3,5-~OCH3)2-C6H3-CH2 P
181 CH3 CH3 3,4~5-(ocH3)3-c6H2-cHz 182 CH3 CH3 2-OC2Hs-C6H4-CH2 183 CH3 CH3 3-OC2Hs-C6H4-CH2 184 CH3 CH3 4-OC2Hs-C6H4-CH2 185 CH3 CH3 2-o-(n-c3H~)-c6H4-cH2 186 C~3 CH3 3-o-(n-C3H7)-C6H4-CH2 187 CH3 CH3 4-O-(n-.C3H7)-C6H4-CHz 188 CH3 CH3 2-o-(i-c3H7)-c6H4-cH2 w 189 CH3 CH3 3-o-(i-c3H7)-c6H4-cH2 w 190 CH3 CH3 4_o-(i-c3H7)-c6H4-cH2 191 CH3 CH3 4-o-(n-C4Hg)-C6H4-CH2 192 CH3 CH3 3-o-(t-c4H9)-c6H4-cH2 193 CH3 CH3 4-o-(n-C6Hl3)-C6H4-CH2 194 CH3 CH3 2-O-Allyl- 4 H4-CH2 195 CH3 CH3 3-O-Allyl-C6H4-CH2 196 CH3 CH3 4-O-Allyl-C6H4-CHz 197 CH3 CH3 2-CF3-C6H4-CH2 . ~3 198 CH3 CH3 3-CF3-C6H4-CH2 Cc~
C~
No . Re Rt Ak Vl o 199 CH3 CH3 4-cF3-c6H4-cH2 200 CH3 CH3 2-Acetyl-C6H4-CH2 ~
201 CH3 CH3 3-Acetyl-C6H4-CH2 202 CH3 CH3 4-Acetyl-C6H4-CH2 203 CH3 CH3 2-Methoxycarbonyl-c6H4-cH2 204 CH3 CH3 3-Methoxycarbonyl-C6H4-CH2 205 CH3 CH3 4-Methoxycarbonyl-C6H4-CH2 206 CH3 CH3 2-Am;noc~rbonyl-C6H4-CH2 207 CH3 CH3 3-Am;no~rbonyl-C6H4-CH2 208 CH3 CH3 4-Am;nocArbonyl-C6H4-CH
209 CH3 CH3 2-Dimethyl~~;noc~rbonyl-c6H4-cH2 210 CH3 CH3 3-Dimethylam;noc~rbonyl-C6H4-CH2 211 CH3 CH3 4-DImethylaminocarbonyl-c6H4-cH2 212 CH3 CH3 2-(N-Methylam;no~rbonyl)-C6H4-CHz 213 CH3 CH3 3-~N-Methylaminoc~rbonyl~-c6H4-cH2 214 CH3 CH3 4-(N-MethylaminocArbonyl)-c6H4-cH2 218 CH3 CH3 2-Aminothiocarbonyl-C6H4-CH
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259 CH3 CH3 2-(3'-Nitrophenoxy)eth-1-yl ~
260 CH3 CH3 2-~4'-NitrorhPnoxy)eth-1-yl O
261 CH3 CH3 2-(2'-Methoxyphenoxy)eth-1-yl 262 CH3 CH3 2-(3'-Methoxyph~no~y)eth-l-yl 263 CH3 CH3 2-(4'-Methoxyph~no~y)eth-1-yl 264 CH3 CH3 2-(2'-Trifluoromethylphenoxy)eth-1-yl265 CH3 CH3 2-(3'-Trifluoromethylphenoxy)eth-l-yl266 CH3 CH3 2-(4'-Trifluoromethylrh~noYy)eth 267 CH3 CH3 2-(2'-Acetylphenoxy)eth-1-yl 268 CH3 CH3 2-(3'-Acetyl~h~noYy)eth-l-yl w 269 CH3 CH3 2-(4'-AcetylphenQYy)eth-l-yl 270 CH3 CH3 2-(2'-Methoxycarbonyl)eth-1-yl 271 CH3 CH3 2-(3'-Methoxycarbonyl)eth-l-yl 272 CH3 CH3 2-(4'-Methoxycarbonyl)eth-l-yl 273 CH3 CH3 2-(2'-Dimethyla~;noc~rbonyl)eth-l-yl 274 CH3 CH3 2-(3~-DLmethylaminoc~rbonyl)eth 27 5 CH3 CH3 2-(4'-Dimethylam;no~Arbonyl)eth-l-yl 276 CH3 CH3 2-(2'-Aminothiocarbonyl)eth-1-yl 277 CH3 CH3 2-(3'-Aminoth; ocArbonyl )eth-l-yl 278 CH3 CH3 2-(4' ~;nothiocarbonyl)eth-1-yl c~
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No. Re R~ Ak o o 379 CH3 CH3 4-chloroth; ~701 -2-ylmethyl P
380 CH3 CH3 5-chloroth; ~701 -2-ylmethyl O
381 CH3 CH3 4-Thiazolylmethyl 382 CH3 CH3 2-Methylth;~z~1-4-ylmethyl 383 CH3 CH3 5-Methylthiazol-4-ylmethyl 384 CH3 CH3 2-chloro~h;~7ol-4-ylmethyl 385 CH3 CH3 5-chloroth~zol-4-ylmethyl 386 CH3 CH3 5-Thiazolylmethyl 387 CH3 CH3 2-Methylth; ~701 -5-ylmethyl 388 CH3 CH3 4-Methylth;~7O1-5-ylmethyl w 389 CH3 CH3 2-chloro~hi~7O1-5-ylmethyl w 390 CH3 CH3 4-chlorothiazol-5-ylmethyl 391 CH3 CH3 3-Isoxazolylmethyl 392 CH3 CH3 4-MethylisoY~zol-3-ylmethyl 393 CH3 CH3 5-Methylieoy~zol-3-ylmeth 394 CH3 CH3 4-chloroisoxazol-3-ylmethyl 395 CH3 CH3 5-chloroisoY~ol-3-ylmethyl 396 CH3 CH3 4-Isoxazolylmethyl 397 CH3 CH3 3-Methylisoxazol-4-ylmethy7 398 CH3 CH3 " 5-Methylisoxazol-4-ylmethyl C~
Cs3 No. R~ Rd Ak o ~
399 CH3 CH3 3-chloroiso~A7Ol-4-ylmethyl ~
400 CH3 CH3 5-chloroiso~701-4-ylmethyl 0 401 CH3 CH3 5-Isoxazolylmethyl 402 CH3 CH3 3-MethylisoY~ 701 -5-ylmethyl 403 CH3 CH3 4-Methyl;so~7sl-5-ylmethyl 404 CH3 CH3 3-chloroiso~7-o1-5-ylmethyl 405 CH3 CH3 4-chloroisoxazol-5-ylmethyl 406 CH3 CH3 3-I~othiazolylmethyl 407 CH3 CH3 4-Methyliso~h; A701 -3-ylmethyl 408 CH3 CH3 5-Methylisoth;~zol -3-ylmethyl 409 CH3 CH3 4-chloroisoth;~ol -3-ylmethyl 410 CH3 CH3 5-chloroiso~h;~ol -3-ylmethyl 411 CH3 CH3 4-Isoth;~701 ylmethyl 412 CH3 CH3 3-Methylisothiazol-4-ylmethyl 4l3 CH3 CH3 . 5-Methylisothi~70l-4-ylmethyl 414 CH3 CH3 3-chloroisothiazol-4-ylmethyl 415 CH3 CH3 5-chloroiso~h;~zol-4-ylmethyl 416 CH3 CH3 5-Isothiazolylmethyl 417 CH3 CH3 3-Methylisothi~701-5-ylmethyl 41B CH3 CH3 4-Methylisothiazol-5-ylmethyl ~~~
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742 CH3 4-Thiazolyl CH3 743 CH3 4-Thiazolyl C2H5 744 CH3 4-Th; ~701 yl n-C3H7 745 CH3 4-Thiazolyl i-c3H7 746 CH3 3-Isoxazolyl H
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752 CH3 5-Isoxazolyl CH3 753 CH3 5_ISOYA701Y1 C2H5 754 CH3 5-TsoY~z~lyl n-C3H7 755 CH3 5-Isoxazolyl i-c3H7 7S6 CH3 2-Imidazolyl H
757 CH3 2-Imidazolyl CH
758 CH3 2-Imidazolyl C2H
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882 OCH3 3_ISOYA70~Y1 CH3 883 OCH3 3-Isoxazolyl C2H5 884 OCH3 3_ISOX~7Q1Y1 n-C3H7 1 885 OCH3 3_ISOYA701Y1 i-C3H7 886 OCH3 5-Isoxazolyl H
887 OCH3 5_ISOXA701Y1 CH3 888 OCH3 5_ISOXA~O1Y1 C2Hs P
889 OCH3 5-Isoxazolyl n-C3H7 890 OCH3 5_ISOYA701Y1 i-C3H7 891 OCH3 2 - T ; ~A701 yl H
892 OCH3 2-Imidazolyl CH3 893 OCH3 2-Imidazolyl C2H5 894 OCH3 2-Imidazolyl n-C3H7 895 OCH3 2-Imidazolyl i-C3H7 896 OCH3 3-Pyrazolyl ~ H
897 OCH3 3-Pyrazolyl CH
898 OCH3 3-Pyrazolyl CzH5 CS~
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1000 OH 2-OY~ZO1Y1 i-C3H7 ~
1001 OH 4-Oxazolyl H
1002 OH 4-Oxazolyl CH3 1003 OH 4-OY~ZO1Y1 C2H5 1004 OH 4-Oxazolyl n-C3H7 1005 OH 2-Thiazolyl i-c3H7 1006 OH 2-Thiazolyl H
1007 OH 2-Thiazolyl CH3 1008 OH 2-Thiazolyl C2H
1009 OH 2-Thiazolyl n-C3H7 1010 OH 2-Thiazolyl i-C3H7 1011 OH 4-Thiazolyl H ~!
1012 OH 4-Thiazolyl CH3 1013 OH 4-Th;~7~1yl C2H5 1014 OH 4-IsoY~zolyl n-C3H7 1015 OH 4-Isoxazolyl i-c3H7 1016 OH 3-Isoxazolyl H
1017 OH ' 3-Isn~zolyl CH
1018 OH 3-Iso~zo~yl C2H5 ~-~
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1019 OH 3-Isoxazolyl n-C3H7 ~
1020 OH 3-Isoxazolyl i-C3H7 ~
1021 OH 5-Isoxazolyl H
1022 OH 5-Isoxazolyl CH3 1023 OH 5_I~OY~7O1Y1 C2Hs 1024 OH 5-Isox~zolyl n-C3H7 1025 OH 5-Isoxazolyl i-C3H7 1026 OH 2-Imidazolyl H
1027 OH 2-Imidazolyl CH3 1028 OH 2-Imidazolyl C2H
1029 OH 2-Imidazolyl n-C3H7 1030 OH 2-Imidazolyl i-C3H7 1031 OH 3-Pyrazolyl H
1032 OH 3-Pyrazolyl CH3 1033 OH 3-Pyrazolyl C2H5 1034 OH 3-Pyrazolyl n-C3H7 1035 OH 3-Pyrazolyl i-C3H7 1036 OH 4-Pyrazolyl H
1037 OH 4-Pyrazolyl CH3 1033 OH 4-Pyrazolyl C2H
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1120 SCH3 SCH3 i-C3H7 1121 SC83 Cyclop.~pyl H
1122 SCH3 Cyclopropyl CH3 1123 SCH3 Cyclopropyl C2H5 1124 SCH3 Cyclopropyl n-C3H7 1125 SC83 CYC1~L~PY1 i-c3H7 1126 Cyclopropyl H H
1127 Cyclopropyl H CH3 1128 Cyclopropyl H C2H5 p 1129 Cyclopropyl H n-C3H7 1130 Cyclopropyl H i-c3H7 1131 Cyclopropyl OH
1132 Cyclopropyl OH CH3 1133 Cyclop~o~yl OH C2H5 1134 Cyclopropyl OH n-C3H7 1135 Cyclopropyl OH i-C3H7 1136 Cyclopropyl Cl n-C4Hg 1137 Cyclopropyl Cl CH3 1138 Cyclopropyl Cl C2H5 ~_~
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o No. Re Rd A~ o o 1179 CH3 3-F-C6H4 3-Methyl-but-2-en-1-yl ~
1180 CH3 4-F-C6H4 H ~
1183 CH3 4-F-C6H4 n-C3H7 1184 CH3 4-F-C6H4 i-C3H7 1185 CH3 4-F-C6H4 n-C4Hg 1186 CH3 4-F-C6H4 t-C4Hg 1187 CH3 4-F-C6H4 n-C6H13 1188 CH3 4-F-C6H4 Prop-1-en-3-yl ~
118g CH3 4-F-C6H4 (E)-1-chloLu~op-l-en-3-yl w 1190 CH3 4-F-C6H4 Propyn-3-yl 1191 CH3 4-F-C6H4 3-Methyl-~ut-2-en-1-yl 1192 CH3 2-Cl-C6H4 H
1193 CH3 2-Cl-C6H4 CH3 1194 CH3 2-Cl-C6H4 C2H5 1195 CH3 2-Cl-C6H4 n-C3H7 1196 CH3 2-Cl-C6H4 i-C3H7 1197 CH3 2-Cl-C6H4 n-C4H
1198 CH3 2-cl-C6H4 t-C4Hg C~
Cs~
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f ~ -No. R Rd Ak o 1199 CH3 2-Cl-C6H4 n-C6Hl3 1200 CH3 2-Cl-C6H4 Prop-l-en-3-yl 1201 CH3 2-Cl-C6H4 ~E)-l-ChloLo~Lo~-l-en-3-yl N
1202 CH3 2-Cl-C6H4 Propyn-3-yl 1203 CH3 2-Cl-C6H4 3-Methyl-but-2-en-1-yl 1204 CH3 3-Cl-C6H4 H
1205 CH3 3-Cl-C6H4 CH3 1206 CH3 3-Cl-C6H4 C2H5 1207 CH3 3-Cl-C6H4 n-C3H7 1208 CH3 3-Cl-C6H4 i-C3H7 120g CH3 3-Cl-C6H4 n-C4H
1210 CH3 3-Cl-C6H4 t-C4Hg 1211 CH3 3-Cl-C6Hg n-C6Hl3 1212 CH3 3-Cl-C6H4 Prop-l-en-3-yl 1213 CH3 3-Cl-C6H4 (E)-l-Chloroprop-l-en-3-yl 1214 CH3 3-Cl-C6H4 ~Gp~.l-3-yl 1215 CH3 3-Cl-C6H4 3-Methyl-but-2-en-1-yl 1216 CH3 4-Cl-C6H4 H
1217 CH3 4-Cl-C6H4 CH3 1218 CH3 4-Cl-C6H4 C2Hs 1219 C~3 4-Cl-C6H~ n-C3H
No. R Rd Ak o 1220 CH3 4-Cl-C6H4 i-C3H7 w 1221 CH3 4-Cl-C6H4 n-C4Hg ~
1222 CH3 4-Cl-C6H4 t-C4Hg O
1223 CH3 4-Cl-C6H4 n-C6H13 1224 CH3 4-Cl-C6H4 Prop-1-en-3-yl 1225 CH3 4-Cl-C6H4 (E)-1-Chloroprop-1-en-3-yl 1226 CH3 4-Cl-C6H4 ~opy~-3-yl 1227 CH3 4-Cl-C6H4 3-Methyl-but-2-en-1-yl 1228 CH3 2,3-Cl2-C6H3 H
1229 CH3 2,3-Cl2-C6H3 CH3 1230 CH3 2,3-Cl2-C6H3 C2H
1231 CH3 2,3-Cl2-C6H3 n-C3H~
1232 CH3 2,3-Clz-C6H3 i-c3H7 1233 CH3 2,3-Cl2-C6H3 n-C4Hg 1234 CH3 2,3-Cl2-C6H3 t-C4Hg 1235 CH3 2,3-Cl2-C6H3 - n-C6Hl3 1236 CH3 2,3-Cl2-C6H3 Prop-1-en-3-yl 1237 CH3 2,3-C12-C6H3 (E)-1-Chloroprop-1-en-3-yl 1238 CH3 2,3-C12-C6H3 ~ yl,-3-yl 1239 CH3 2,3-C12-C6H3 3-Methyl-but-2-en-1-yl 1240 CH3 2,4-C12-C6H3 H
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~ !-No. R Rd Ak o 1283 CH3 3,4-C12-C6H3 n-CcHl3 1284 CH3 3,4-Cl2-C6H3 Prop-l-en-3-yl p 1285 CH3 3,4-Cl2-C6H3 (E)-1-Chloroprop-l-en-3-yl O
1286 CH3 3,4-C12-C6H3 . ~Lo~yl~-3-yl 1287 CH3 3,4-C12-C6H3 3-Methyl-but-2-en-1-yl 1288 CH3 3,5-C12-C6H3 H
1289 CH3 3,5-C12-C6H3 CH3 1290 CH3 3,5-Cl2-C6H3 CzH5 1291 CH3 3,5-Cl2-C6H3 n-C3H7 1292 CH3 3,5-C12-C6H3 i-C3H7 i293 CH3 3~5-C12-C6H3 n-C4Hg N
1294 CH3 3,5-Cl2-C6H3 t-C4Hg 1295 CH3 3,5-Cl2-C6H3 n-C6Hl3 1296 CH3 3,5-Cl2-C6H3 Prop-l-en-3-yl 1297 CH3 3,5-C12-C6H3 (E)-l-Chloroprop-l-en-3-yl -1298 CH3 3,5-Cl2-C6H3 Propyn-3-yl 1299 CH3 3,5-C12-C6H3 3-Methyl-~ut-2-en-1-yl 1300 CH3 2-Br-C6H4 H
1301 C~3 2-Br-C6H4 CH3 1302 CH3 2-Br-C6H4 C2H5 1303 CH3 2-Br-C6H4 n-C3H7 C~
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~ No. R Rd Ak o 1410 CH3 2-NO ff 6H4 C2H5 . p 1411 CH3 2-NO2-C6H4 n-C3H7 o 1412 CH3 2-NO2-C6H4 i-C3H7 1413 CH3 2-NO2-C6H4 n-C4Hg 1414 CH3 2-NO2-C6H~ t-C4H9 1415 CH3 2-NO2-C6H4 n-C6Hl3 1416 CH3 2-NO2-C6H4 Prop-l-en-3-yl - 1417 CH3 2-NO2-C6H4 ~E)-l-ChloLoy~oy-l-en-3 1418 CH3 2-NO2-C6H4 Propyn-3-yl 1419 CH3 2-NO2-C6H4 3-Methyl-but-2-en-1-yl w 1423 CH3 3-NO2-C6H4 n-C3H7 1424 CH3 3-NO2-C6H4 i-c3H7 1425 CH3 3-NO2-C6H4 n-C4Hg 1426 CH3 3-NOz-C6H4 t-C4Hg 1427 CH3 3-NO2-C6H4 n-C6H13 1428 CH3 3-NO2-C6H4 Prop-l-en-3-yl .
1429 CH3 3-N02-C6H4 (E)-l-Chloroprop-l-en-3-yl C~
il~ 0050/45204 2199~22 ,i , _I
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No. R Rd Ak o 1451 CH3 2-CH3-C6H4 n-C6Hl3 1452 CH3 2-CH3-C6H4 Prop-1-en-3-yl ~
1453 CH3 2-CH3-C6H4 (E)-1-Chloroprop-1-en-3-yl O
1454 CH3 2-CH3-C6H4 Propyn-3-yl 1455 CH3 2-CH3-C6H4 3-Methyl-but-2-en-1-yl 1459 CH3 3-CH3-C6H4 n-C3H~
1460 CH3 3-CH3-C6H4 i-C3H7 1461 CH3 3-CH3-C6H4 n-C4Hg w 1462 CH3 3-CH ff 6H4 t-C4Hg 1463 CH3 3-CH3-C6H4 n-C6H13 1464 CH3 3-CH3-C6H4 Prop-1-en-3-yl 1465 CH3 3-CH3-C6H4 (E)-l-Chloroprop-1-en-3-yl 1466 CH3 3-CH3-C6H4 Propyn-3-yl 1467 CH3 3-CH3-C6H4 3-Methyl-but-2-en-1-yl 1471 CH3 4-CH3-C6H4 n-C3H7 ~_~
CD
No. R Rd Ak o 1472 CH3 4-CH3-C6H4 i-C3H7 o 1473 CH3 4-CH3-C6H4 n-C4H
1474 CH3 4-CH3-C6H4 t-C4Hg O
1475 CH3 4-CH3-C6H4 n-C6Hl3 1476 CH3 4-CH3-C6H4 Prop-l-en-3-yl 1477 CH3 4-CH3-C6H4 (E)-l-ChloLo~Lo~-1-en-3-yl 1478 CH3 4-CH3-C6H4 ~-o~yl.-3-yl 1479 CH3 4-CH3-C6H4 3-Methyl-but-2-en-1-yl 1480 CH3 2,3-(CH3)z-C6H3 H
1481 CH3 2,3-(CH3)2-C6H3 CH3 1482 CH3 2,3-(CH3)2-C6H3 C2H
1483 CH3 2,3-(CH3)2-C6H3 n-C3H7 1484 CH3 2,3-(CH3)2-C6H3 i-c3H7 1485 CH3 2,3-(CH3)2-C6H3 n-C4Hg 1486 CH3 2,3-(CH3)2-C6H3 t-C4Hg 1487 CH3 2,3-(CH3)2-C6H3 n-C6Hl3 1488 CH3 2,3-(CH3)2-C6H3 Prop-l-en-3-yl 1489 CH3 2,3-(CH3)2-C6H3 (E)-l-ChloLopLu~-l-en-3-yl 1490 CH3 2,3-(CH3)2-C6H3 Propyn-3-yl 1491 CH3 2,3-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl ~3 1492 CH3 2,4-(CH3~2-C6H3 H ~_~
No. R Rd A~ g 1493 CH3 2,4-(CH3) ff 6H3 CH
1494 CH3 2,4-(CH3)2-C6H3 C2Hs 1495 CH3 2,4-(CH3) ff 6H3 n-C3H7 o 1496 CH3 2,4-(CH3)2-C6H3 i-C3H7 1497 CH3 2,4-(CH3)2-C6H3 n-C4H
1498 CH3 2,4-~CH3)2-C6H3 t-C4Hg 1499 CH3 2,4-(CH3)2-C6H3 n-C6H13 1500 CH3 2,4-(CH3)2-C6H3 Prop-1-en-3-yl 1501 CH3 2,4-(CH3)2-C6H3 (E)-1-Chloroprop-1-en-3-yl 1502 CH3 2,4-~CH3)2-C6H3 Propyn-3-yl lS03 CH3 2,4-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl w 1504 CH3 2,5-(CH3)2-C6H3 H
1505 CH3 2,5-(CH3)2-C6H3 CH3 1506 CH3 2,5-(CH3)2-C6H3 C2H5 1507 CH3 2,5-(CH3)2-C6H3 n-C3H7 1508 CH3 2,5-(CH3)2-C6H3 i-C3H7 lS09 CH3 2,5-(CH3)2-C6H3 n-C4Hg 1510 CH3 2,5-(CH3) ff 6H3 t-C4Hg 1511 CH3 2,5-(CH3)2-C6H3 n-C6Hl3 1512 CH3 2,5-(CH3)2-C6H3 Prop-1-en-3-yl 1513 CH3 2,5-(CH3)2-C6H3 (E)-1-Chloroprop-1-en-3-yl C~
No. R Rd A~ g lS14 CH3 2,5-(CH3)2-C6H3 Propyn-3-yl 0 1515 CH3 2,5-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl ~
i516 CH3 2,6-(CH3)2-C6H3 H o i517 CH3 - 2,6-(CH3)2-C6H3 CH3 1518 CH3 2,6-(CH3)2-C6H3 C2Hs 1519 CH3 2,6-(CH3)2-C6H3 n-C3H7 1520 CH3. 2,6-(CH3)2-C6H3 i-C3H7 1521 CH3 2,6-(CH3)2-C6H3 n-C4H9 1522 CH3 2,6-(CH3)2-C6H3 t-C4Hg 1523 CH3 2,6-(CH3)2-C6H3 n-C6H13 1524 CH3 2,6-(CH3)2-C6H3 Prop-1-en-3-yl w 1525 CH3 2,6-(CH3)2-C6H3 (E)-l-Chloroprop-1-en-3-yl 1526 CH3 2,6-(CH3)2-C6H3 Propyn-3-yl 1527 CH3 2,6-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl 1528 CH3 3,4-(CH3)2-C6H3 H
1529 CH3 3~4-(cH3)2-c6H3 CH3 1530 CH3 3,4_(CH3)2-C6H3 C2H5 1531 CH3 3,4-(CH3)2-C6H3 n-C3H7 1532 CH3 3,4-(CH3)2-C6H3 i-C3H7 1533 CH3 3~4-(cH3)2-c6H3 n-C4H
1534 CH3 3,4-(CH3)2-C6H3 t-C4Hg C~
, f ~ ~
No. R Rd Ak o 1535 CH3 3,4-(C83)2-C6H3 n-C6Hl3 1536 CH3 3,4-(CH3) ff 6H3 ~rop-1-en-3-yl . ~
1537 CH3 3,4-(CH3)2-4H3 (E)-1-Chlo~o~G~ en-3-yl O
1538 CH3 3,4_~CH3)2-C6H3 Propyn-3-yl 1539 CH3 3,4-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl 1540 CH3 3,5-(CH3)2-C6H3 H
1541 CH3 3,5-(CH3)2-C6H3 CH3 1542 CH3 3,5-(CH3)2-C6H3 C2H5 1543 CH3 3,5-(CH3)2-C6H3 n-C3H7 1544 CH3 3,5-(CH3)2-C6H3 i-C3H7 1545 CH3 3,5-(CH3)2-C6H3 n-C4H
1546 CH3 3,5-(CH3)2-C6H3 t-C4Hg 1547 CH3 3,5-(CH3)2-C6H3 n-C6H13 1548 CH3 3,5-(CH3)2-C6H3 Prop-l-en-3-yl 1549 CH3 3,5-(CH3)z-C6H3 (E)-1-Chlolo~o~-1-en-3-yl 1550 CH3 3,5-(CH3)2-C6H3 Propyn-3-yl 1551 CH3 3,5-(CH3) ff 6H3 3-Methyl-but-2-en-1-yl 1552 CH3 2-C2Hs-C6H4 H
1553 CH3 2-C2Hs-C6H4 CH3 1554 CH3 2-C2H5-C6H~ C2H5 1555 CH3 2-C2Hs-C6H4 n-C3H7 f ~ ~ ~, ,.
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No. R Rd Ak o 1577 CH3 4-CzHs-C6H4 CH
1578 CH3 4-C2Hs-C6H4 C2Hs 1579 CH3 4-C2Hs-C6H4 n-C3H7 N
1580 CH3 4-C2Hs-C6H4 i-C3H7 1581 CH3 4-C2Hs-C6H4 n-C4Hg 1582 CH3 4-C2Hs-C6H4 t-C4Hg 1583 CH3 4-C2Hs-C6H4 n-C6H13 1584 CH3 4-C2Hs-C6H4 Prop-l-en-3-yl 1585 CH3 4-C2H5-C6H4 (E)-l-ChluLo~Lup-l-en-3-yl 1586 CH3 4-C2Hs-C6H4 Propyn-3-yl 1587 CH3 4-C2Hs-C6H4 3-Methyl-but-2-en-1-yl 1588 CH3 2-i-C3H7-C6H4 H
1589 CH3 2-i-C3H7-C6H4 CH3 1590 CH3 2-i-C3H7-C6H4 C2H5 1591 CH3 2-i-C3H7-C6H4 n-C3H7 1592 CH3 2-i-C3H7-C6H4 i-C3H7 1593 CH3 2-i-c3H7-c6H4 n-C4Hg 1594 CH3 2-i-C3H7-C6H4 t-C4Hg 1595 CH3 2-i-C3H7-C6H4 n-C6H13 1596 CH3 2-i-c3H7-c6H4 Prop-l-en-3-yl r~
1597 CH3 2-i-C3H7-C6H4 (E)-l-ChloLo~Lo~-l-en-3-yl CS~
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No. R Rd Ak o 1619 CH3 4-i-C3H7-C6H4 n-C6H13 ~
1620 CH3 4-i-C3H7-C6H4 Prop-l-en-3-yl 1621 C~3 4-i-C3H7-C6H4 (E)-1-Chloroprop-l-en-3-yl 1622 CH3 4-i-C3H7-C6H4 Propyn-3-yl 1623 CH3 4-i-C3H7-C6H4 3-~ethyl-but-2-en-1-yl 1626 CH3 2-OH-C6H4 C2Hs 1627 CH3 2-OH-C6H4 n-C3H7 1628 CH3 2-OH-C6H4 i-C3H7 1629 CH3 2-OH-C6H4 n-C4Hg 163Q CH3 2-OH-4H4 t-C4Hg 1631 CH3 2-oH-c6H4 n-C6Hl3 1632 CH3 2-OH-C6H4 Prop-1-en-3-yl 1633 CH3 2-OH-C6H4 (E)-1-Chloroprop-1-en-3-yl 1634 CH3 2-OH-C6H4 Propyn-3-yl 1635 CH3 2-OH-C6H4 3-Methyl-but-2-en-1-yl 1638 CH3 3-OH-C6H4 C2Hs 1639 CH3 3-OH-C6H4 n-C3H7 4 f~
No. R Rd Ak g 1640 CH3 3-OH-C6H4 i-C3H7 o 1641 CH3 3-OH-C6H4 n-C4H9 w 1642 CH3 3-OH-C6H4 t-C4Hg O
1643 CH3 3-OH-C6H4 n-C6H13 1644 CH3 3-OH-C6H4 Prop-1-en-3-yl 1645 CH3 3-OH-C6H4 (E)-1-Chloroprop-1-en-3-yl 1646 CH3~ 3-OH-C6H4 Propyn-3-yl 1647 CH3 3-OH-C6H4 3-Methyl-but-2-en-1-yl 1651 CH3 4-OH-C6H4 n-C3H7 1652 CH3 4-OH-C6H4 i-C3H7 1653 CH3 4-OH-C6H4 n-C4H9 1654 CH3 4-OH-4H4 t-C4Hg 16SS CH3 4-OH-C6H4 n-C6H13 16S6 CH3 4-OH-C6H4 Prop-1-en-3-yl 1657 CH3 4-OH-C6H4 (E)-1-Chlolo~o~-1-en-3-yl 1658 CH3 4-OH-C6H4 Propyn-3-yl 1659 CH3 4-OH-C6H4 3-Methyl-but-2-en-1-yl ~~~
f~ - ~
--No. R Rd Ak o 1662 CH3 2-OCH3-C6H4 C2Hs . ~
1663 CH3 2-OCH3-C6H4 n-C3H7 O
1664 CH3 2-OCH3-C6H4 i-C3H7 1665 CH3 2-OCH3-C6H4 n-C4Hg 1666 CH3 2-OCH3-C6H4 t-C4Hg 1667 CH3 2-OCH3-C6H4 n-C6Hl3 1668 CH3 2-OCH3-C6H4 Prop-1-en-3-yl 1669 CH3 2-OCH3-C6H4 (E)-1-Chloroprop-l-en-3-yl 1670 CH3 2-OCH3-C6H4 Propyn-3-yl 1671 CH3 2-OCH3-C6H4 3-Methyl-but-2-en-1-yl 1672 CH3 3-OCH3-c6H4 H
1673 CH3 3_oCH3-C6H4 CH3 1674 CH3 3_OCH3-C6H4 C2H5 1675 CH3 3_OCH3-C6H4 n-C3H7 1676 CH3 3-OCH ff 6H4 i-C3H7 1677 CH3 3-OCH3-C6H4 n-C4Hg 1678 CH3 3_OCB ff 6H4 t-C4Hg 1679 CH3 3-OCH3-C6H4 n-C6Hl3 1680 CH3 3-OCH3-C6H4 Prop-1-en-3-yl 1681 CH3 3_oCH3-C6H4 tE)-1-Chloroprop-l-en-3 ~ 0050/45204 2~99~22 ,, ' ,, a) ~' i ,.~ ~ -.~ ~ o J~ ru7 U U ~ U U ~ ~ ~ ~ 5 U U ~ 1-5~ m ~ 5~ r C~ 5 5r ,~ ~ 5~ m L sr r m ~ m _, ~ m O O 0 0 o o ~ ~ O O O U
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m m m m :~ r m mU Ux :': mu mu m m IU o U U U u u No. R Rd Ak o 1850 CH3 2-NH2-C6H4 Pxopyn-3-yl O
1851 CH3 2-NH2-C6H4 3-Methyl-but-2-en-l-yl 1852 CH3 3-NH2-C6H4 H o 1853 CH3 3-NH ff 6H4 CH3 1855 CH3 3-NH2-C6H4 n-C3H7 1856 CH3 3-NH2-C6H4 i-C3H7 1857 CH3 3-NH2-C6H4 n-C4Hg 1858 CH3 3-NH2-C6H4 t-C4Hg 1859 CH3 3-NH2-C6H4 n-C6HI3 1860 CH3 3-NH2-C6H4 Prop-l-en-3-yl P
1861 CH3 3-NH2-C6H4 ~E)-l-Chloroprop-l-en-3-yl 1862 CH3 3-NH2-C6H4 Propyn-3-yl 1863 CH3 3-NH2-C6H4 3-Methyl-but-2-en-1-yl 1867 CH3 4-NH ff 6H4 n-C3H7 1868 CH3 4-NH ff 6H4 i-C3H7 1869 CH3 4-NH2-C6H4 n-C4Hg 1870 CH3 4-NH2-C6H4 t-C4Hg C~
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~o~o.o.oooooooooooooooooo No. R Rd Ak o 2018 CH3 4-SCH ff 6H4 Propyn-3-yl 2019 CH3 4-SCH3-C6H4 3-Methyl-but-2-en-1-yl ~
2020 CH3 2-Methylsulfonyl-C6H4 H o 2021 CH3 2-Methylsulfonyl-C6H4 CH3 2022 C~3 2-Methylsulfonyl-C6H4 C2H5 2023 CH3 2-Methylsulfonyl-C6H4 n-C3H7 2024 CH3 2-Methylsulfonyl-C6H4 i-C3H7 2025 C~3 2-Methylsulfonyl-C6H4 n-C4H9 2026 CH3 2-Methylsulfonyl-C6H4 t-C4Hg 2027 CH3 2-Methylsulfonyl-C6H4 n-C6H13 2028 CH3 2-Methylsulfonyl-C6H4 Prop-1-en-3-yl ~
2029 CH3 2-Methylsulfonyl-C6H4 (E)-l-Chloroprop-1-en-3-yl w 2030 CH3 2-Methylsulfonyl-C6H4 Propyn-3-yl 2031 CH3 2-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2032 CH3 3-Methylsulfonyl-C6H4 H
2033 CH3 3-Methylsulfonyl-C6H4 CH3 2034 CH3 3-Hethylsulfonyl-C6H4 C2H5 2035 CH3 3-Methylsulfonyl-C6H4 n-C3H7 2036 CH3 3-Methylsulfonyl-C6H4 i-C3H
2037 C~3 3-Methylsulfonyl-C6H4 n-C4H
2038 CH3 3-Methylsulfonyl-C6H4 t-C4H
No. R Rd Ak o 2039 CH3 3-Methylsulfonyl-C6H4 n-C6Hl3 2040 CH3 3-Methylsulfonyl-C6H4 Prop-1-en-3-yl ~
2041 CH3 3-Methylsulfonyl-C6H4 (E)-l-Chloroprop-l-en-3-yl O
2042 CH3 3-Methylsulfonyl-C6H4 Propyn-3-yl 2043 CH3 3-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2044 CH3 4-Methylsulfonyl-C6H4 H
2045 CH3 4-Methylsulfonyl-C6H4 CH3 2046 CH3 4-Methylsulfonyl-C6H4 C2H5 2047 CH3 4-Methylsulfonyl-C6H4 n-C3H7 2048 CH3 4-Methylsulfonyl-C6H4 i-c3H
2049 CH3 4-Methylsulfonyl-C6H4 n-C4Hg 2050 CH3 4-Methylsulfonyl-C6H4 t-C4Hg 2051 CH3 4-Methylsulfonyl-C6H4 n-C6H13 2052 CH3 4-Methylsulfonyl-C6H4 Prop-l-en-3-yl 2053 CH3 4-Methylsulfonyl-C6H4 (B)-1-Chloroprop-l-en-3-yl 2054 CH3 4-Methylsulfonyl-C6H4 Propyn-3-yl 2055 CH3 4-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2056 CH3 2-Methoxyc~rbo~yl-C6H4 H
2057 CH3 2-Methoxycarbonyl-C6H4 CH
2058 CH3 2-Methoxycarbonyl-C6H4 C2H5 . ~_~
2059 CH3 2-Methoxycarbonyl-C6H4 n-C3H7 CC~
No. R Rd Ak o 2060 CH3 2-Methoxycarbonyl-C6H4 i-c3H7 2061 CH3 2-Methoxycarbonyl-C6H4 n-C4Hg 2062 CH3 2-Methoxycarbonyl-C6H4 t-C4Hg 2063 CH3 2-Methoxycarbonyl-C6H4 n-C6H13 2064 CH3 2-Methoxycarbonyl-C6H4 Prop-l-en-3-yl 2065 CH3 2-Methoxycarbonyl-C6H4 (E)-1-Chloroproe-l-en-3-yl 2066 CH3 2-Methoxycarbonyl-C6H4 Propyn-3-yl 2067 CH3 2-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2068 CH3 3-Methoxycarbonyl-C6H4 H
2069 CH3 3-Methoxycarbonyl-C6H4 CH3 2070 CH3 3-Methoxycarbonyl-C6H4 C2H
2071 CH3 3-Methoxycarbonyl-C6H4 n-C3H7 2072 CH3 3-Methoxycarbonyl-C6H4 i-c3H7 2073 CH3 3-Methoxycarbonyl-C6H4 n-C4Hg 2074 CH3 3-Methoxycarbonyl-C6H4 t-C4Hg 2075 CH3 3-Methoxycarbonyl-C6H4 n-C6H13 2076 CH3 3-Methoxycarbonyl-C6H4 Prop-1-en-3-yl 2077 CH3 3-Methoxycar~onyl-C6H4 (E)-1-Chloroprop-1-en-3-yl 2078 CH3 3-Methoxycar~onyl-C6H4 ~v~y~-3-y 2079 CH3 3-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2080 CH3 4-Methoxycarbonyl-C6H4 H
C~
No. R Rd Ak o 2081 CH3 4-Methoxycarbonyl-C6H4 CH
2082 CH3 4-Methoxycarbonyl-C6H4 C2H
2083 CH3 4-Methoxycarbonyl-C6H4 n-C3H7 O
2084 CH3 4-Methoxycarbonyl-C6H4 i-C3H7 2085 CH3 4-Methoxycarbonyl-C6H4 n-C4Hg 2086 CH3 4-Methoxycarbonyl-C6H4 t-C4Hg 2087 CH3 4-Methoxycarbonyl-C6H4 n-C6H13 2088 CH3 4-Methoxycarbonyl-C6H4 Prop-l-en-3-yl 2089 CH3 4-Methoxycarbonyl-C6H4 ~E)-1-Chlo~ o~-1-en-3-yl 2090 CH3 4-Methoxycarbonyl-C6H4 Propyn-3-yl 2091 CH3 4-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2092 CH3 2-Bthoxycarbonyl-C6H4 H
2093 CH3 2-Ethoxycarbonyl-C6H4 CH3 2094 CH3 2-Ethoxycarbonyl-C6H4 C2H5 20g5 CH3 2-Ethoxycarbonyl-C6H4 n-C3H7 2096 CH3 2-Ethoxycarbonyl-C6H4 i-C3H7 2097 CH3 2-Ethoxycarbonyl-C6H4 n-C~Hg 2098 CH3 2-Ethoxycarbonyl-4 H4 t-C~Hg 2099 CH3 2-Ethoxycarbonyl-C6H4 n-C6H13 2100 CH3 2-Ethoxycarbonyl-C6H4 Prop-l-en-3-yl 2101 CH3 2-Ethoxycarbonyl-C6H4 (E)-1-Chloroprop-l-en-3-yl ~~~
C~
~3 No. R Rd Ak ~
2102 CH3 2-Ethoxycarbonyl-C6H4 Propyn-3-yl O
2103 CH3 2-Ethoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2104 CH3 3-Ethoxycarbonyl-C6H4 H o 2105 CH3 3-Ethoxycarbonyl-C6H4 CH3 2106 CH3 3-Ethoxycarbonyl-C6H4 CzH5 2107 CH3 3-Ethoxycarbonyl-C6H4 n-C3H7 2108 CH3- 3-Ethoxycarbonyl-C6H4 i-C3H7 2109 CH3 3-Ethoxycarbonyl-C6H4 n-C4Hg 2110 CH3 3-Ethoxycarbonyl-C6H4 t-C4Hg 2111 CH3 3-Ethoxycarbonyl-C6H4 n-C6H13 2112 CH3 3-Ethoxycarbonyl-C6H4 Prop-1-en-3-yl 2113 CH3 3-Ethoxycarbonyl-C6H4 ~E)-1-ChloLo~Lo~-1-en-3-yl 2114 CH3 3-Ethoxycarbonyl-C6H4 ~ u~y~l-3-yl 2115 CH3 3-Ethoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2116 CH3 4-Ethoxycarbonyl-C6H4 H
2117 CH3 4-Ethoxycarbonyl-C6H4 CH3 2118 CH3 4-Ethoxycarbonyl-C6H4 C2H
2119 CH3 4-Ethoxycarbonyl-C6H4 n-C3H7 2120 CH3 4-Ethoxycarbonyl-C6H4 i-C3H7 2121 CH3 4-Ethoxyc~rhonyl-C6H4 n-C4Hg 2 2122 CH3 4-Ethoxycarbonyl-C6H4 t-C4Hg Cc~
t~
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No. R Rd Ak g 2144 CH3 3-Aminocarbonyl-C6H4 i-C3H7 O
2145 CH3 3-Aminocarbonyl-C6H4 n-C4Hg p 2146 CH3 3-Am;noc~rbonyl-C6H4 t-C4Hg O
2147 CH3 3-Aminoc~rbonyl-C6H4 n-C6H13 2148 CH3 3-Aminocarbonyl-C6H4 Prop-l-en-3-yl 2149 CH3 3-pminoc~rbonyl-c6H4 (E)-1-Chloroprop-l-en-3-yl 2150 CH3 3-Am;noc~rbonyl-c6H4 Propyn-3-yl 2151 CH3 3-Aminocarbonyl-C6H4 3-Methyl-~ut-2-en-1-yl 2152 CH3 4-Aminoc~rbonyl-C6H4 H
2153 CH3 4-Aminoc~rbonyl-c6H4 CH3 2154 CH3 4-Aminocarbonyl-C6H4 C2H
2155 CH3 4-Aminocarbonyl-C6H4 n-C3H7 2156 CH3 4-Am;nocArbonyl-C6H4 i-C3H7 2157 CH3 4-Aminocarbonyl-C6H4 n-C4Hg 2158 CH3 4-Aminocarbonyl-C6H4 t-C4Hg 2159 CH3 4_Aminoc~rbonyl-C6H4 n-C6H13 2160 CH3 4-Aminocarbonyl-C6H4 Prop-l-en-3-yl 2161 CH3 4-Aminocarbonyl-C6H4 ~E)-1-Chloroprop-1-en-3-yl 2162 CH3 4-Am;noc~rbonyl-C6H4 Propyn-3-yl 2 2163 CH3 4-Aminoc~rbonyl-c6H4 3-Methyl-but-2-en-1-yl Cs~
2164 CH3 2-(N-Methylaminoc~rbonyl)-c6H4 H C~
f 1 ~
No. R Rd Ak o 2165 CH3 2-(N-Methylaminocarbonyl)-C6H4 CH3 O
2166 CH3 2-(N-Methylaminocarbonyl)-C6H4 C2H
2167 CH3 2-(N-Methylaminocarbonyl)-C6H4 n-C3H7 O
2168 CH3 2-(N-Methylaminocarbonyl)-C6H4 i-C3H7 2169 CH3 2-(N-Methylam; noc~ rbonyl)-C6H4 n-C4Hg 2170 CH3 2-(N-Methylam;noc~rbonyl)-C6H4 t-C4Hg 2171 CH3 2-(N-Methylaminocarbonyl)-C6H4 n-C6H13 2172 CH3 2-(N-Methylam; noC~ rbonyl)-C6H4 Prop-1-en-3-yl 2173 CH3 2-(N-Methylaminocarbonyl)-C6~4 (E)-l-Chloroprop-1-en-3-yl 2174 CH3 2-(N-Methylaminocarbonyl)-C6H4 ~L u~ -3-yl 2175 CH3 2-(N-Methy1~;noc~rbonyl)-C6H4 3-Methyl-but-2-en-1-yl 2176 CH3 3-(N-Methylam;noc~rbonyl)-c6H4 H
2177 CH3 3-(N-Methylaminocarbonyl)-C6H4 CH3 2178 CH3 3-(N-Methylami noc~rbonyl ) -C6H4 C2H5 2179 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 n-C3H7 2180 CH3 3-(N-Methylaminoc~rbonyl)-C6H4 i-C3H7 2181 CH3 3-(N-Methylaminoc~rbonyl)-c6H4 n-C4Hg 2182 CH3 3-(N-Methylaminoc~rbonyl)-C6H4 t-C4Hg 2183 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 n-C6Hl3 2184 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 Prop-l-en-3-yl 2185 CH3 3-(N-Methylam;noc~rbonyl)-c6H4 (E)-1-Chloroprop-1-en-3-yl ~D
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Z ~ ~ ~ N ~I ~ ~ ~' No. R Rd Ak o 2207 CH3 2-Dimethylam;noc~rbonyl-C6H4 n-C6H13 ~
2208 CH3 2-Dimethylaminocarbonyl-C6H4 Prop-1-en-3-yl 2209 CH3 2-Dimethylaminqc~rbonyl-C6H4 ~E)-l-Chloroprop-l-en-3-yl O
2210 CH3 2-Dimethylam;nocArbonyl-C6H4 Propyn-3-yl 2211 CH3 2-Dimethylam;noc~rbonyl-C6H4 3-Methyl-but-2-en-1-yl 2212 CH3 3-Dimethylaminoc~rho~yl-C6H4 H
2213 CH3 3-Dimethylaminocarbonyl-C6H4 CH3 2214 CH3 3-Dimethylaminoc~rbonyl-c6H4 C2Hs 2215 CH3 3-Dimethylaminocarbonyl-C6H4 n-C3H7 2216 CH3 3-Dimethylaminoc~rbonyl-C6H4 i-C3H7 2217 CH3 3-DimethylaminocArhnnyl-C6H4 n-C4Hg P
2218 CH3 3-Dimethylam;nQc~rbonyl-c6H4 t-C4H9 2219 CH3 3-Dimethylaminocarbonyl-C6H4 n-C6H13 2220 CH3 3-Dimethylaminoc~rbonyl-C6H4 Prop-1-en-3-yl 2221 CH3 3-DimethylaminocArbonyl-C6H4 (E)-1-Chloroprop-1-en-3-yl 2222 CH3 3-Dimethyla~;nocArho~yl-C6H4 Propyn-3-yl 2223 CH3 3-Dimethylaminoc~rbo~yl-C6H4 3-Methyl-but-2-en-1-yl 2224 CH3 4-Dimethylam;noc~rbonyl-C6H4 H
2225 CH3 4-Dimethylam;noc~rbonyl-C6H4 CH
2226 CH3 4-Dimethylam;noc~r~onyl-c6H4 C2H5 C~
2227 CH3 4-Dimethylaminoc~-bonyl-C6H4 n-C3H7 Co 2~99422 ,. . ..
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Table 1251 Compounds of the general formula I.A (n 2 O) in which UR' i8 5 methoxyamino, VR~' is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1252 10 Co,.l~ounds of the general formula I.A (n = 0) in which UR' is ~ ethoxyamino, VR" i8 methoxy, ya iS -CHzO-# (-# = bond to Aa) and Aa corresponds to one of the y-v~S stated in Table A
Table 1253 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is ethoxy, ya is -CH20-# (-# = bond to Aa) and Aa corresponds to one of the yL~Up8 stated in Table A
20 Table 1254 Compounds of the general formula I.A (n 2 o) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2S-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1255 Compounds of the general formula I.A (n = 0) in which UR' is ethoxyamino, VR" is methoxy, ya iS -CH=CH- and Aa corresponds to 30 one of the groups stated in Table A
; Table 1256 Compounds of the general formula I.A (n = 0) in which UR~ is 35 methoxyamino, VR" is methoxy, ya iS -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1257 40 Compounds of the general formula I.A (n = 0) in which UR' i5 methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a co,..pound corresponding to one of the y~U~S stated in Table C
~1~942~
Table 1258 C~."~ ds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and S Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ylo~s stated in Table C
Table 1259 Co,..~v~,lds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-$ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CHsNORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 1260 Compounds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1261 Compounds of the general formula I.A ~n ~ 0) in which UR' i8 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa~ and Aa is 2,S-dimethylphenyl which carries a radical CH=N0Riii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~, Table 1262 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa i8 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a cv,,,~o~nd corresponding to one of the groups stated in Table C
Table 1263 Co...~vullds of the general formula I.~ (n = 0) in which UR' is methoxyamino, VR" is methoxy, Y~ is -CH20-~ bond to Aa) and 45 Aa is 2-chloro-5-methylphenyl which carries a radical CH=NORiii in 2199~22 the 4 position, Riii for a compound corresponding to one o~ the y~OU~S stated in Table C
Table 1264 Cu...~unds of the general formula I.A (n z 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 1265 Compounds of the general formula I.A (n ~ 0) in which UR' is 15 methoxyamino, VRn is methoxy, ya is -CHzO-~ (-# - bond to Aa) and ( Aa is phenyl which carries a radical CH=NORiii in the 3 position, Riii for a c~ ou~d corresponding to one Of the groups stated in Table C
20 Table 1266 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 25 position, Riii for a cv...p~ul,d corresponding to one of the groups stated in Table C
Table 1267 30 Compounds of the general formula I.A (n 5 0) in which UR' i8 ~- methoxyamino, VR" is ~ethoxy, ya is -CH2O-~ = bond to A~) and . Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y~u~3 stated in Table C
Table 1268 Compounds of the general f ormula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to A~) and 40 Aa is 2-~ethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 1269 C~ ou.lds o~ the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1270 Compounds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 1271 Co,l.~ou,-ds of the general formula I.A (n - 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1272 Co~pounds of the general formula I.A (n - 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 C(CH3)=NORiii in the 4 position, Riii for a compound corresponding ~- to one of the groups stated in Table C
Table 1273 35 C~ /~unds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ (-* - bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)sNORiii in the 4 position, Riii for a cc~.poulld corresponding to one of the groups stated in Table C
Table 1274 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -cH20 - ~ (-# 2 bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in _ 478 2 1 9 9ll 2 2 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1275 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# - bond to Aal and A~ is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups lO stated in Table C
Table 1276 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and ( Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the S position, Rili for a co~"~ound corresponding to one of the groups stated in Table C
20 Table 1277 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)-NOR~ii in the 4 25 pos~tion, Riii for a compound corresponding to one of the groups stated in Table C
Table 1278 30 C~ ounds of the general formula I.A (n = O) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1279 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv..,~o~nd corresponding to one of the groups stated in Table C
2~99i22 Table 1280 Compounds of the general formula I.A (n s 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 5 Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a col.lp~und corresponding to one of the groups stated in Table C
Table 1281 Compounds of the general ~ormula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
~' Table 1282 CG,..y~unds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# ~ bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv..~o~ild corresponding to one of the groups stated in Table C
25 Table 1283 Co"l~ounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-* (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 30 C(CH2CH3)-NoRiii in the 4 position, Riii for a c~...~,.d corresponding to one of the groups stated in Table C
Table 1284 35 C~ ounds of the general formula I.A (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, ya is -CH20-~ (-* = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1285 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-* (-# = bond to Aa) and 45 Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 ~ 2199122 position, Riii for a c~ vund corresponding to one of the yLvU~s stated in Table C
Table 1286 Co,,.~ounds of the general formula I.A (n = 0~ in which UR' is methoxyamino, VRn is methoxy, ya is -CH20-# ( -# 2 bond to Aa) and Aa i~ 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a co~..pv~nd corresponding to one of the 10 groups stated in Table C
Table 1287 CoI,.pounds of the general formula I.A (n 2 O) in which UR' is 15 methoxyamino, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 1288 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 25 the 4 position, Riii for a co.l,~o~"d corresponding to one of the groups stated in Table C
Table 1289 30 Compounds of the general formula I.A (n e o) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~.llpou"d corresponding to one of the groups stated in Table C
Table 1290 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is - CH20-# ( - # 2 bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cvll,~ound corresponding to one of the y ~ OU~3 stated in Table C
U05~/45~U4 ~ 481 2199422 Table 1291 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-~ 5 bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1292 Cu,.l~o~l-ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# ( -# e bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cG,..~ound 15 corresponding to one of the groups stated in Table C
( , .
Table 1293 C~..*ou~.ds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya is -CH20-# t-~ = bond to A~) and Aa is 2-chloro-5-methylphenyl which carrie~ a radical C(CH2CH2CH3)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1294 Compounds of the general for~~ I.A (n = 0) in which UR' i5 methoxyamino, VR~' is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical 30 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~o,..~o~nd corresponding to one of the groups stated in Table C
~. .
Table 1295 35 Compounds of the general formula I.A (n 5 O) in which UR' is methoxyamino, VR~ is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the stated in Table C
Table 1296 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# ~-~ = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1297 Compounds of the general formula I.A (n=0) in which UR' is ethoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1298 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1299 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1300 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1301 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2:~99422 Table 1302 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and 5 Aa is 2,5-dimethylphenyl which carries a radical ClCH(CH3)2]=NOR
in the 4 position, Riii for a cv...~ound corresponding to one of the groups stated in Table C
Table 1303 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH2O-~ (-* = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound lS corresponding to one of the yLO~S stated in Table C
Table 1304 Co,.*oulLds of the general formula I.A (n = 0~ in which UR' is 20 methoxyamino, VR" i8 methoxy, ya i8 -CH20-# (-# 2 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1305 Compounds of the general formula I.A (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, ya i8 -CH20-# (~~ - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CtCH(CH3) 2]=NoRiii 30 in the 4 position, Riii for a ~v...~ou.ld corresponding to one of the groups stated in Table C
Table 1306 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# ~-~ = bond to Aa) and Aa is phenyl which carries a radical CtCH(CH3) 2 ]-NORiii in the 3 position, Riii for a ~."~ound corresponding to one of the groups stated in Table C
Table 1307 C~",~o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in , 2 1 994~2 the S position, Rii$ for a co~ ound corresponding to one of the groups stated in Table C
Table 1308 CG~ u~.ids of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a c~ und corresponding to one of the groups 10 stated in Table C
Table 1309 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6Hs)sNORiii in the 4 position, Riii for a compound corresponding to one of the yLo~s stated in Table C
20 Table 1310 Co...~oullds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -cH2o-# (~~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6H5)2NORiii in the 25 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1311 30 Co,..~ur.ds of the general formula I.A (n = 0) in which UR~ i8 methoxyamino, VRn i8 methoxy, ya i8 -CH20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Ri$$ for a col"~ound corresponding to one of the groups stated in Table C
Table 1312 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a col,.pound corresponding to one of the groups stated in Table C
Table 1313 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and 5 Aa i8 2-methyl-5-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a ~Gr.~ nd corresponding to one of the groups stated in Table C
Table 1314 Compounds of the general formula I.A (n s 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Ri$i for a compound corresponding 15 to one of the groups stated in Table C
( Table 1315 Compounds of the general formula I.A (n - 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1316 Compounds of the general formula I.A ~n = 0) in which UR' is methoxyamino, VR~ is methoxy, ya i8 -cH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5~=NORiii in the 3 30 position, Riii for a compound corresponding to one o~ the yr Oh~S
stated in Table C
Table 1317 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 5 position, Rii~ for a compound corresponding to one of the yl~u~R
stated in Table C
Table 1318 Compounds of the general for~ula I.~ (n = 0) in which UR' is ~ethoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and 45 Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 ~, 2~99122 position, RLii for a ~o~ o~nd corresponding to one of the groups stated in Table C
Table 1319 C ,o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a co."~o~lld corresponding to one of the groups 10 stated in Table C
Table 1320 C~m~u~lds of the general formula I.A (n = 0) in which UR' i8 1~ methoxyamino, VR is methoxy, ya i8 -CH20-# (-# = bond to Aa) and ( Aa is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a col.,~ound corresponding to one of the groups stated in Table C
20 Table 1321 Compounds of the general for.mula I.A ~n 5 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1322 30 Compounds of the general formula I.A (n = 0) in which UR' is l methoxyamino, VRn is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a ~o..,~oulld corresponding to one of the groups stated in Table C
Table 1323 CoL,I~o~.,ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and 40 Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NOR
in the 4 position, Rii~ for a compound corresponding to one of the groups sta,ted in Table C
2199~22 Table 1324 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and 5 Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORii~
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1325 Compounds of the general formula I.A (n ~ 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a C61LI~UI1d corresponding to one of the 15 groups stated in Table C
Table 1326 Compounds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a _ oulld corresponding to one of the ~L~U~S
stated in Table C
25 Table 1327 Co,l,pGundg of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a rad~cal C(Cl)=NORiii in the 5 30 position, Rlii for a ~l~ound corresponding to one of the yLOu~g stated in Table C
Table 1328 35 Compounds of the general formula I.A (n = 0) in which UR~ is methoxyamino, VR~' is methoxy, ya iS -CH20-# (~~ = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co~ Gu--d corresponding to one of the groups stated in Table C
Table 1329 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 2199~2~
4 position, Riii for a co _u,ld corresponding to one of the y~vU~S
stated in Table C
Table 1330 s Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C~SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 1331 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=~ORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 1332 C_ l~unds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)-NORiii in 25 the 4 position, Riii for a ~o,..~und corresponding to one o~ the groups stated in Table C
Table 1333 30 Compound~ of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a ov,..~ound corresponding to one of the groups stated in Table C
Table 1334 C~l..p~u~lds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# ~ bond to A~) and 40 A~ is 2-chloro-5-methylphenyl which carr~es a radical C(SCH3) -N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
.
-00~0/452~4 g9~2~
48g Table 1335 Cu~ u~l~ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# - bond to Aa) and 5 Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)-NORiii in the 4 position, Riii for a co...~ou.~d corresponding to one of the y~ps stated in Table C genannten GL ~p~er, entsprich Table 1336 Co,..~vul~ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 1337 Co,..~oul~ds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(SCH3)-NORiii in the 5 position, Riii for a cv...~ou.~d corresponding to one of the groups stated in Table C
25 Table 1338 Compounds of the general formula I.A ~n = 0) in which UR' is methoxyamino, VR" ic methoxy, ya iS -CH20-# (-# = bond to Aa) and A~ is phenyl which carries a radical C(cyclopropyl)=NORiii in the 30 4 position, Riii for a compound corre~ponding to one of the yLv~
stated in Table C
Table 1339 35 C~ll.pounds of the general formula I.A (n = 0) in which UR' i methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)sNORiii in the 4 position, Riii for a cv,ll~ound corresponding to one of the groups stated in Table C
Table 1340 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ # = bond to Aa) and 45 Aa i8 2-fluorophenyl which carries a radical C(cyclopropyl)--NOR
9 ~ 2 2 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1341 Cl ~o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa iB 2-chlorophenyl which carries a radical C(cyclopropyl)=NOR
in the 4 position, Riii for a compound corresponding to one of the 10 groups stated in Table C
Table 1342 Cv~ ds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and ( Aa is 2,5-dimethylphenyl which carries a radical C(cyclopropyl)sNORiii in the 4 position, Riii for a cv,..~oulld corresponding to one of the groups stated in Table C
20 Table 1343 C~ ~u,.ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 position, Riii for a cvl.*ound corresponding to one of the groups stated in Table C
Table 1344 30 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)-NORili in the 4 position, Riii for a co...~u.,d corresponding to one of the groups stated in Table C
Table 1345 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ bond to Aa) and 40 Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii ~or a cc~..~o~..d corresponding to one of the groups stated in Table C
2~99~22 Table 1346 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ # = bond to Aa) and 5 Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a c~ oul-d corresponding to one of the groups stated in Table C
Table 1347 Cor..~oùllds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the lS ylOU~S stated in Table C
( 'rable 1348 C~l,~o~nds of the general formula I.A (n 3 0) in which UR' is 20 methoxyamino, VRn iS methoxy, ya is -CH20-# (-# - bond to A~) and Aa is phenyl which carries a radical C(CF3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1349 CGmp~u,lds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 13S0 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 ~osition, Riii for a compound corresponding to one of the groups stated in 'rable C
Table 1351 Compound~ of the general formula I.A (n = 0) in which UR' i~
methoxyamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to A~) and 45 Aa is 2-chlorophenyl which carries a radical C(CF3)=NORii~ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1352 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1353 Compounds of the general formula I.A (n-0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CR3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1354 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1355 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1356 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1357 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and S Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1358 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH2S-# (-# = bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for 15 each compound to a line of Table D
Table 1359 Compounds of the general formula I.A in which UR' is ~ 20 methoxyamino, VR is methoxy, ya iS -CH2S-# (-~ - bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each c~r..~o~.ld to a line of Table D
25 Table 1360 Compounds of the general formula I.A in which UR' is methoxyamino, VR" i5 methoxy, ya iS -cH2o-# (-~ - bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 30 position of the thiazolyl ring and Xn corresponding for each , compound to a line of Table D
~...
Table 1361 35 Compounds of the general formula I.A in which UR' is methoxyamino, VRn is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1362 Co. oul,ds of the general formula I.A in which UR' is methoxyamino, VR~ is methoxy, Y~ is -CH2S-# (-~ = bond to Aa) and 4~ Aa is oxazol-2-yl, the combination of the substituent in the 4 -2199~22 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1363 C~ unds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the c~mh~nation of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 1364 Co~ G~nds of the general formula I.A in which UR' is 15 methoxyamino, VR" is methoxy, ya is -cH2s-# ~-# 2 bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the co~h~ n~tion of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 1365 Co~ ds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 1,2,4-oxad~azol-5-yl, the combination of the substituent in 2~ the 3 position of the oxadiazolyl ring and Xn corre~ponding for each compound to a line of Table D
Table 1366 30 C~ o~-,ds of the general formula I.A in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH2S-~ ~-# ~ bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the c~ h~nAtion of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1367 CG..I~ounds of the general formula I.A in which UR' is methoxyamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 40 Aa i8 1,2,4-thiadiazol-5-yl, the cnmh;n~tion of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1368 Compounds of the general formula I.A in which UR' is methoxyamino, VR~ is methoxy, ya i8 -CH2S-~ = bond to Aa) and 5 Aa is isoxazol-2-yl, the c~mh; n~tion of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each cG.t.~o~lld to a line of Table D
Table 1369 Co,..pounds of the general formula I.A in which UR' is methoxyamino, VR" i~ methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is isoxazol-2-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 15 compound to a line of Table D
Table 1370 Compounds of the general formula I.A in which UR' is 20 methoxyamino, VRn is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is isothiazol-2-yl, the combination of the substituent in the position of the isothiazolyl ring and Xn corresponding for each co~ o~nd to a line of Table D
25 Table 1371 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and Aa is isothiazol-2-yl, the combination of the substituent in the 5 30 position of the isothiazolyl ring and Xn corresponding for each co.,.~o~nd to a line of Table D
Table 1372 35 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa i8 pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1373 CG...~vunds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and 45 Aa is pyrazol-3-yl, the combination of the substituent in the 1 496 2199~22 position of the pyrazolyl ring and Xn corresponding for each co..,~ou,~d to a line of Table D
Table 1374 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-~ s bond to Aa) and Aa i8 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 1375 Compounds of the general formula I.A in which UR' is 15 methoxyamino ~ VRn i8 methoxy, ya is -CH20-~ (-# e bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each c~,.,p~.,d to a line of Table D
20 Table 1376 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in 25 the 1 position of the 1,2,4-triazol ring and Xn corresponding for each c~,.,~o~nd to a line of Table D
Table 1377 30 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazol ring and Xn corresponding for each co1l,pound to a line of Table D
Table 1378 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb iS oxygen and Ab for a ~ d 40 corresponds to one of the groups stated in Table E
Table 1379 Compounds of the general formula I.B (n = 0) in which UR' is 45 methoxyamino, VR" is ethoxy, yb iS oxygen and Ab for a c~.,.~u~.d corresponds to one of the groups stated in Table E
2~9912~
Table 1380 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is sulfur and Ab for a compound corresponds to one of the groups stated in Table E
Table 1381 Compounds of the general formula I.B (n - 0) in which UR' is 10 methoxyamino, VRn is ethoxy, yb iS sulfur and Ab for a c~ ~und corresponds to one of the groups stated in Table E
Table 1382 15 CGrll~unds of the general formula I.B (n e O) in which UR' is ~~ methoxyamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the co~h;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1383 Co~ o~nds of the general formula I.B (n s 0) in which UR' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is phenyl, thi~
25 phenyl radical carrying an -Oo~R~ group in the 3 position and the cnmh~n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1384 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 35 corresponding for each compound to a line of Table F
Table 1385 Co.,.~ -ds of the general formula I.B (n = 0) in which UR' is 40 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
498 2 ~ 9 9 ~ ~ 2 Table 13B6 Cofil~u~ds of the general. formula I.B ~n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, 5 this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the c~mh;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table Table 1387 Compounds of the general formula I.B (n = o) in which U~' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each cv.,.~ound to a line of Table F
Table 1388 C~l..pounds of the general formula I.B (n = 0) in which UR' i5 20 methoxyamino, VR" i~ methoxy, yb i8 oxygen and Ab 1~
pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~"l~ ,d to a line of Table F
25 Table 1389 CG.,.~ou..ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VRn is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
30 group in the 2 position and the comhin~tion of the index o and of the R~ group corresponding for each co.l.~u~.ld to a line of Table F
Table 1390 35 Compound~ of the general formula I.B (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ,uund to a line of Table F
Table 1391 Cv...~o~lds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyrazinyl, 45 this 2 p~L azinyl radical carrying an -Oo~R~ group in the 6 , . . . .
~199~22 4g9 position and the aomh; nation of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1392 Cor,-~o~,ds o~ the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the cnmh;~~tion of the index o and of 10 the R~ group corresponding for each cG",~Gulld to a line of Table G
Table 1393 Cum~o~nds of the general formula I.B (n = 0) in which UR' is 15 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is ~~ pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the combination of the index o and of the R~ group corresponding for each co,~,~ou~ld to a line of Table G
20 Table 1394 CGl,.~unds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radiaal carrying an - Oo~R~
25 group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 1395 30 C- _unds of the general formula I.B (n = 0) in which UR' i8 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
group in the 4 position and the combination of the index o and of the R~ group corresponding for each c~ ound to a line of Table G
Table 1396 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 40 pyrimidin-4-yl, thi3 pyrimidin-4-yl radical aarrying an -Oo~R~
group in the 2 position and the c~mh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table G
2199~2 Table 1397 Compounds of the general formula I.B (n = 0) in which UR' i5 methoxya~ino, VRn is ethoxy, yb iS oxygen and Ab i5 5 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the cnmh;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 1398 Co~ Gu~,ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 15 corresponding for each compound to the substituents stated in a ( line of Table H
Table 1399 20 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each c~ ound to the substituents stated in a 25 line of Table H
Table 1400 Compounds of the general formula I.B (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy, yb i8 oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 1401 Compounds of the general formula I.B (n z 0) in which UR' i8 methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
0050/45~4 ~ 501 2199422 Table 1402 C~ uu~ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 5 pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each ~ ..d to the substituents stated in a line of Table H
10 Table 1403 Co..,~uul-ds of the general formula I.B (n 2 O) in which UR' is methoxyamino, VRn is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an 15 R~-substituted phenoxy group in the 4 position and the R~ group f corresponding for each compound to the substituents stated in a line of Table H
Table 1404 CG.I.~ounds of the general formula I.B (n e O) in which UR' i5 methoxyamino, VR" is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 25 corresponding for each compound to the substituent~ stated in a line of Table H
Table 1405 30 Compounds of the general formula I.B (n e O) in which UR' is methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is ( 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each cv...~ound to the substituents stated in a 35 line of Table H
.
Table 1406 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxyamino, VR" is methoxy, yc ~s CHsC(Cl)-C(=0)-0-# (-# z bond to AC) and Ac for a co~ o~nd corresponds to a group of Table I.l ~5 -~ 502 2~99~22 Table 1407 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-o-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.l Table 1408 Cv...~oul-ds of the general formula I.C (n - 0) in which UR' is 10 ethoxyamino, VR" is ethoxy, yc i8 CH=C(Br)-C(=0)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.l Table 1409 15 Compounds of the general formula I.C (n = 0) in which UR' is ( methoxyamino, VR" is methoxy, yc is CH=c(Br)-c(=o)-o-# (-# = bond to AC) and Ac for a cv...~o~L~.d corresponds to a group of Table I.1 Table 1410 Co...pounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is cH=c(~r)-c(=o)-o-# (-# = bond to AC) and Ac for a ~-c...~ound corresponds to a group of Table I.1 25 Table 1411 Compounds of the general formula I.C (n = 0) in which UR' is ethoxyamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-0-# (-# = bond to AC) and Ac for a corl-~ound correspond~ to a group of Table I.l Table 1412 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc is CH=c(No2)-c(=o)-o-# (-# = bond 35 to AC) and Ac for a colllpo~L~,d corresponds to a group of Table I.1 Table 1413 CG~ vul~ds of the general formula I.C (n - 0) in which UR' is 40 methoxyamino, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-# = bond to AC) and Ac for a cv~ ouLld corresponds to a group of Table I.l 0050/45~04 2199~22 Table 1414 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VRn is methoxy, yc is CH=C(Cl)-C(=O)-NH-# (-# = bond 5 to A~) and Ac for a compound corresponds to a group of Table I.2 Table 1415 CGl"~oullds of the general formula I.C (n = 0) in which UR' is 10 methoxyamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-NH-# (-# 2 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1416 15 Co.~ou~ds of the general for~ul~ I.C (n = 0) in which UR' is methoxyamino, VR~ i8 methoxy, yc is CH-C(~r)-C(=O)- NH-# (-# =
bond to AC) and Ac for a cv,-~und corresponds to a group of Table I.2 20 Table 1417 Compounds of the general form~ I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH-C(Br)-C(=0)-NH-# (-# - bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1418 Compounds of the general formula I.C (n - 0) in which UR' is methoxyamino, VR~ i8 methoxy, yc is CH=C(CN)-C(=0)-NH-# (-# = bond 30 to AC) and Ac for a compound corresponds to a group of Table I.2 ( Table 1419 Compounds of the general formula I.C (n = 0) in which UR' is 35 methoxyamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1420 40 Co,!,~ou.,ds of the general formula I.C (n = 0) in which UR' ~8 methoxyamino, VR" is methoxy, yc is CH=C(N02)-C(=0)-NH-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 2199~22 Table 1421 Compounds of the general formula I.C (n = 0) in which UR' i9 methoxyamino, VR" is ethoxy, yc is CHzC(N02)-C(=0)-NH-~ (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1422 Col"~ounds of the general formula I.C (n ~ 0) in which UR' is 10 methoxyamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-~ =
bond to AC) and Ac for a ~v...~o~nd corresponds to a grou~ of Table I.2 Table 1423 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-~ (-# =
bond to AC) and Ac for a cv.~.poulld corresponds to a group of Table I.2 Table 1424 Compounds of the general formula I.C (n 2 0) in which UR' is methoxyamino, VR" is methoxy, yc is CHsC(Br)-C(-0)-N(CH3)-# (-# =
Z5 bond to AC) and Ac for a co.,.~ound corresponds to a group of Table I.2 Table 1425 30 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VRn is ethoxy, yc i~ CH=C(Br)-C(=0)-N(CH3)-# (-~ =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 35 Table 1426 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and AC for a compound corresponds to a group of Table 40 I.2 -2199~22 Table 1427 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, ~R" is ethoxy, Y~ is CH=C(CN)-C(=0)-N(CH3)~
5 bond to A~) and A~ for a cv.~.~und corresponds to a group of Table I.2 Table 1428 10 C~.-~oul-ds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc i8 CH=C(NO2)-C(=O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 15 Table 1429 CG~ unds of the general for~l~l A I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH-C(N02)-C(=0)-N~CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table 20 I.2 Table 1430 CG.,Ipou~lds of the general formula I.D (n = 0) in which UR' is 25 methoxyamino, VR" is methoxy and Ad for a co~l~y~u~ld corresponds to a group of Table J
Table 1431 30 Compounds of the general formula I.D (n = 0) in which UR' is - methoxya~ino, VR" i8 ethoxy and Ad for a cv.. ~ound corresponds to a ( group of Table J
Table 1432 Compounds of the general formula I.E (n = 0) in which UR' is methoxyamino, VR" is methoxy, ye -CH=N0-~ (-# = bond to Ae) and Ae for a compound corresponds to a group of Table K.l 40 Table 1433 Compounds of the general formula I.E (n = 0) in which UR' is methoxyamino, VR" is ethoxy, ye - CH=NO-# ( ~~ = bond to Ae) and AQ
for a compound corresponds to a group of Table K.1 0050/4520g .
506 2~99422 Table 1434 Compounds of the general formula I.E (n s 0) in which UR' is methoxyamino, VR" i8 methoxy, ye -cH=N-NH-# (-~ = bond to Ae) and 5 A~ for a ~~vmpo~nd corresponds to a group of Table K.2 Table 1435 Compounds of the general formula I.E (n = 0) in which UR' is 10 methoxyamino, VR" is ethoxy, ye -CH=N-NH-# (-# = bond to Ae) and Ae for a ~v...~nd corresponds to a group of Table K.2 Table 1436 15 C ~Lounds of the general form~ I.F (n z 0) in which UR' is ( methoxyamino, VRn is methoxy and Af is the radical -N=CRgRh, Rg being methyl and Rh for a cor..pou.~d corresponding to a group of Table L
20 Table 1437 C~ _ unds of the general formula I.F (n = 0) in which UR' i~
methoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a c~ ound corresponding to a group of 25 Table L
Table 1438 Compounds of the general formula I.F (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy and Af is the radical -N-CRgRh, R9 ~- being ethyl and Rh for a c~.~l~ou~.d correspon~ng to a group of Table L
Table 1439 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1440 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 45 being n-propyl and Rh for a cGI,,po~nd corresponding to a group of Table L
2I99~22 Table 1441 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg 5 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1442 10 cor..pounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is methoxy and Af is the radical -N=CR9Rh, Rg being cyclo~op~l and Rh for a c~...~ulld corresponding to a group of Table L
15 Table 1443 Col..pou.lds of the general formula I.F (n 5 O) in which UR' is methoxyamino, VR" is ethoxy and Af i~ the radical -N=CRgRh, Rg being cyclopropyl and Rh for a compound corresponding to a group 20 of Table L
Table 1444 Co.--pounds of the general formula I.F (n = 0) in which UR' is 25 methoxyamino, VR" is methoxy and Af i5 the radical -N=CR9Rh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
Table 1445 - Compounds of the general formula I.F (n = 0) in which UR' ismethoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1446 Co...~oullds of the general formula I.F (n = 0) in which UR' is methoxyamino, VRn is methoxy and Af i5 the radical -N=CRgRh, Rg 40 being methylthio and Rh for a co..l~o~d corresponding to a group o~
Table L
508 ~ I 9 9 ~ 2 2 Table 1447 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VRn i8 ethoxy and Af is the radical -N=CR9Rh, R9 5 being methylthio and Rh for a col,l~oul~d corresponding to a group of Table L
Table 1448 10 compounds of the general formula I.F (n = 0) in which UR' iB
methoxyamino, VR" is methoxy and Af is the radical -N~CR9Rh, Rg being cyano and Rh for a compound corresponding to a group of Table L
15 Table 1449 f Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being cyano and Rh for a compound corresponding to a group of 20 Table L
Table 1450 Compounds of the general formula I.G (n = 0) in which UR' is -25 methoxyamino, VR" is methoxy, Yg is oxygen and Ag for a compound corresponds to a group of Table M
Table 1451 30 Compounds of the general formula I.G (n = 0) in which UR' i8 ! methoxyamino, VRn is ethoxy, Yg iB oxygen and A9 for a ~o.. ~ound corresponds to a group of Table M
Table 1452 Compounds of the general formula I.G (n = 0) in which UR' i5 methoxyamino, VR~ is methoxy, Y9 is sulfur and Ag for a compound corresponds to a group of Table M
40 Table 1453 Compounds of the general formula I.G (n = 0) in which UR' iB
methoxyamino, VR" is ethoxy, Yg i~ sulfur and Ag for a co...~ound corresponds to a group of Table M
-~. og 2199~22 Table 1454 Compounds of the general formula I.H (n = m = 0) in which UR' is methoxyamino, VR" is methoxy and Ah for a c~".~ound corresponds to 5 a group of Table N
Table 1455 Compounds of the general formula I.H (n = m = 0) in which UR' is 10 methoxyamino, VR" is ethoxy and Ah for a ~o..~oul.d corresponds to a group of Table N
Table 1456 15 Co..lp~nds of the general formula I.K (n = 0) in which UR' is methoxyamino, VR" is methoxy, Rf is hydrogen and the combination of the substituents Ret Rd and Ak corresponds for each co...~ound to a line of Table 0 20 Table 1457 Compounds of the general formula I.K (n = 0) in which UR' is methoxyamino, VR" i8 ethoxy, Rf i8 hydrogen and the combination of the substituents Ret Rd and Ak corresponds for each compound to a 25 line of Table 0 Table 1458 Compounds of the general formula I.A (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy, ya is CH=CH- and Aa i8 a - heterocyclic structure, this heterocyclic structure corresponding for each co~"~ound to a line of Table D.l Table 1459 Compounds of the general formula I.A (n = 0) in which UR' i3 methoxyamino, VR" is ethoxy, ya iS CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each co."~o~nd to a line of Table D.1 The novel c~ ou~ds of the formula I are suitable for controlling harmful fungi and An;r-l pests from the class comprising insects, arachnids and nematodes. They can be used in crop protection and 45 in the hygiene, material protection and veterinary sectors as fungicides and pesticides.
.
219~2 The insect pests include:
from the order of the butterflies (Lepidoptera), for exa~ple Adoxophyes orana, Agrotis ypsilon, Agrotis segetum, Alabama 5 argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Cacoecia murinana, Capua reticulana, Choristoneura fumiferana, Chilo partellus, Choristoneura occidentalis, Cirphis unipuncta, Cnaphalocrocis me~i n~l; S ~
Crocidolomia binotalis, Cydia pomonella, Dendrolimus pini, 10 Diaphania nitidalis, Diatraea grandiosella, Earias insulana, palpus lignosellus, Eupoecilia ambiguella, Feltia-subterranea, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, ~eliothis zea, Hellula lln~ s~ Hibernia defoliaria, Hyphantria cunea, Hyponomeuta 15 malinellus, Keiferia lycopersicella, Lambdina fiscellaria, f Laphygma exigua, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Manduca sexta, Malacosoma neustria, Mamestra brassicae, Mocis repanda, Operophthera 20 brumata, Orgyia pseudotsugata, O~trinia nubilalis, Pandemis heparana, Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Phyllocnistis citrella, Pieri~ brassicae, Plathypena scabra, Platynota stultana, Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodenia ornithogalli, Pseudoplusia 25 includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sesamia inferens, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Syllepta derogata, Synanthedon myopaeformis, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Tryporyza incertulas, Zeiraphera 30 canadensis, also Galleria mellonella and Sitotroga cerealella, c Ephestia cautella and Tineola bisselliella;
from the order of the beetles (Coleoptera), for ~Y~mrle Agriotes lineatus, Agriotes obscurus, Anthonomus grandis, Anthonomus 3s pomorum, Apion vorax, Atomaria linearis, Blastophagus piniperda, Cassida nebulosa, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchus napi, Chaetocnema t;h;~l1s, Conoderus vespertinus, Crioceris asparagi, Dendroctonus refipennis, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, 40 Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus bras;l;~nsis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus C~JI'~ ; S, Meligethes aeneus, Melolontha 45 h1ppocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllopertha horticola, Phyllophaga sp., Phyllotreta 511 23 99~2~
chrysocephala, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Psylliodes napi, Scolytus intricatus, Sitona lineatus, also Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Sitophilus granaria, La5ioderma serricorne, Oryzaephilus 5 surinamensis, Rhy~opertha dominica, Sitophilus oryzae, tribolium castaneum, Trogoderma granarium and Zabrotes subfasciatus;
from the order of the Diptera, for ~Y~mple Anastrepha ludens, Ceratitis capitata, Contarinia sorghicola, Dacus cucurbitae, 10 Dacus oleae, Dasineura brassicae, Delia coarctata, Delia radicum, Hydrellia griseola, Hylemyia platura, Liriomyza sativae;
Liriomyza trifolii, Mayetiola destructor, Orseolia oryzae, Oscinella frit, Pegomya hyoscyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis 15 pomonella, Tipula oleracea, Tipula paludosa, also Aedes aegypti, Aedes vexans, Anopheles maculipennis, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, 20 Haplodiplosis equestris, Hypoderma lineata, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Musca domestica, Muscina stabulans, Oestrus ovis, Tabanus bovinus and Simulium damnosum;
from the order of the Thysanoptera, for example Fr~nk~ n; ella 25 fusca, Frankliniella occidentalis, Fr~nkl;n;ella tritici, Haplothrips tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
~rom the order of the Hymenoptera, for e~r~ e Athalia rosae, 30 Atta cephalotes, Atta sexdens, Atta t~Y~n~, Hoplocampa minuta, Hoplocampa testudinea, Iridv,,.yl ~~ humilis, Iridomyrmex purpureus, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta and Solenopsis richteri;
35 from the order of the Heteroptera, for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus hesperus, Lygus lineolaris, Lygus pratensis, Nezara viridula, 40 Piesma quadrata, Solubea insularis and Thyanta perditor;
from the order of the Homoptera, for ~mple Acyrthosiphon onobrychis, Acyrthosiphon pisum, Adelges laricis, Aonidiella aurantii, Aphidula nasturtii, Aphis fabae, Aphis gossypii, Aphis 45 pomi, Aulacorthum solani, Bemisia tabaci, Brachycaudus cardui, Brevicoryne brassicae, Dalbulus maidis, Dreyfusia nor~-nn;anae, Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosoma ~ ................................... ~.... ..
219g~22 lanigerum, Laodelphax striatella, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzus persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Perkinsiella saccharicida, Phorodon humuli, 5 Planococcus citri, Psylla mali, Psylla piri, Psylla pyricol, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Saissetia oleae, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogatella furcifera, Toxoptera citricida, trialeurodes abutilonea, trialeurodes vaporariorum and Viteus vitifolii;
from the order of the termites (Isoptera), for example C~lotermes flavicollis, Leucot ~s flavipes, Macrot~rm~s subhyalinus, Odontotermes formosanus, Reticulitermes lucifugus and Termes natalensis;
from the order of the Orthoptera, for example Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, 20 Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Schistocerca gregaria, also Acheta domestica, Blatta orientalis, Blattella germanica and Periplaneta americana;
from the order of the Arachnoidea, for ex~ _le phytophagous 25 mite~, such as Aculops lycopersicae, Aculops pelekassi, Aculus schlechtendali, Brevipalpus phoenicis, Bryobia praetiosa, Eotetranychus carpini, Eutetranychus banksii, Eriophyes sheldoni, Oligonychus pratensis, Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Tarsonemus 30 pallidus, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranchus pacificus, Tetranychus urticae, ticks such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes 35 rubicundus, Ornithodorus moubata, Otobius megnini, Rhipicephalus appendiculatus and Rhipicephalus evertsi, and zooparasitic mites, such as Dermanyssus g~ n~e, Psoroptes ovis and Sarcoptes scabiei;
40 from the class of the nematodes, for example root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, and Meloidogyne javanica, cyst-forming nematodes, eg. Globodera pallida, Globodera rostochiensis, Heterodera avenae, Heterodera glycines, and Heterodera schachtii, migratory endoparasites and 45 semiendoparasitic nematodes, eg. Heliocotylenchus multicinctus, Hirsch~-nn;ella oryzae, Hoplolaimus spp, Pratylenchus brachyurus, Pratylenchus fallax, Pratylenchus penetrans, Pratylenchus vulnus, .
0050~45204 21994~2 Radopholus similis, Rotylenchus reniformis, Scutellonema brady~, and Tylenchulus semipenetrans, leaf and stem nematodes, eg.
Anguina tritici and Aphelenchoides besseyi, Ditylenchus angustus, and Ditylenchus dipsaci, virus vectors, eg. Longidorus spp, 5 Trichodorus christei, Trichodorus viruliferus, Xiphinema index and Xiphinema mediterraneum.
The active ingredient can be used as such, in the form of their form~llAtions or the application forms prepared therefrom, for 10 example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents, granules, by spraying, nebulizing, dusting, broadcasting or pouring. The application forms depend entirely on the intended uses; they should in any 15 case ensure very fine distribution of the novel active ingredients.
Some of the compounds of the formula I have systemic fungicidal activity. They can be used as foliar and soil fungicides against 20 a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phy~v~l~y~2tes and Basidiomycetes.
They are particularly important for controlling a large number of 25 fungi on various crops, such as wheat, rye, barley, oats, rice, maize, lawns, cotton, soybean, coffee, sugar cane, grapevines, fruit trees, ornamentals and vegetable plants, such as cucumbers, beans and cucurbitaceae, as well as on the seeds of these plants.
30 The cv,,.~oul.ds I are particularly suitable for controlling the ~- following plant diseases:
* Erysiphe graminis (powdery mildew) in cereals, * Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbitaceae, * Podosphaera leucotricha on apples, * Uncinula necator on grapevines, * Puccinia species on cereals, * Rhizoctonia species on cotton and lawns, 40 * Ustilago species on cereals and sugar cane, * Venturia inaequalis (scab) on apples, * Helminthosporium species on cereals, * Septoria nodorum on wheat, * Botrytis cinerea (gray mold) on strawberries and grapevines, 45 * Cercospora arachidicola on peanuts, * Pseudocercosporella herpotrichoides on wheat and barley, * Pyricularia oryzae on rice, .
OU50/45Z~4 ~ 514 21 ~9~2~
* Phytophthora infestans on potatoes and tomatoes, ~ Fusarium- and Verticillium species on various plants, * Plasmopara viticola on grapevines, * Alternaria species on vegetables and fruit.
The novel compounds may also be used in material protection twood preservation), for e~mrle against Paecilomyces variotii.
They can be converted into the conventional formulations, such as 10 solutions, emulsions, suspensions, dusts, powders, pastes or granules. The application forms depend on the particular intended use; they should in any case ensure very fine distribution of the active ingredients.
15 The formulations can be prepared in a known manner, for ~YAmple by extending the active ingredient with solvents and/or carriers, if desired with the use of emulsifiers and dispersants, it being possible also to use other organic solvents as auxiliary solvents when water is used as a diluent.
Suitable assistants for this purpose are essentially:
- solvents, such as aromatics (eg. xylene), chlorinated aromatics ~eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol and butanol), ketones (eg.
cyclohexanone)~ amines (eg. ethanolamine and dimethylfor~-~;de) and water;
- carriers, such as crushed natural minerals (eg. kaolins, al~ n~Q, talc and chalk) and crushed synthetic minerals (eg.
finely divided silica and silicates);
- emulsifiers, such as nonionic and anionic emulsifiers (eg.
polyoxyethylene fatty alcohol ethers, alkanesulfonates and arylsulfonates) and - dispersants, such as ligninsulfite waste li~uors and methylcellulose.
Suitable surfactants are alkali metal, ~lk~l~ne earth metal and ammonium salts of aromatic sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of 40 fatty acids, alkanesulfonates and alkylarylsulfonates, alkylsulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of 45 naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol polyglycol ethers, .~
_ 515 2~99~22 tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, 5 sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Aqueous application forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation 10 of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adherents, dispersants or emulsifiers.
However, it is also possible to prepare concentrates which consist of active ingredient, wetting agents, adherents, 15 dispersants or emulsifiers and possibly solvent or oil and which ( are suitable for dilution with water.
Powders, broadcasting agents and dusting agents can be prepared by mixing or by m; 11 i ng the active ingredients together with a 20 solid carrier.
Granules, for ~mrl e coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
Solid carriers are minerals, such as silica gels, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate and magnesium oxide, milled plastics, fertilizers, such as 30 ammonium sulfate, A -nium phosphate, r ;um nitrate and ureas, f- and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.
The active ingredient concentrations in the ready-to-use formulations can be varied within relatively wide ranges.
Very generally, the compositions contain from 0.0001 to 95~ by weight of active ingredient.
Formulations contA;n;ng more than 95% by weight of active 40 ingredient can be successfully applied by the ultra-low-volume (ULV) method, in which case it is even possible to use the active ingredient without additives.
For use as fungicides, concentrations of from 0.01 to 95, 45 preferably from 0.5 to 90, % by weight of active ingredient are advisable. For use as insecticides, formulations cont~;n;ng from 2199~22 0.0001 to 10, preferably from 0.01 to 1, ~ by weight of active ingredient are suitable.
The active ingredients are usually used in a purity of from 90 to 5 100%, preferably from 95 to 100% (according to NMR spectrum).
Examples of such formulations are:
I. a solution of 90 par~s by weight of a novel cv.. ~ound I
and 10 parts by weight of N-methyl-~-pyrrolidone, which solution is suitable for use in the form of very fine drops;
II. a solution of 20 parts by weight of a novel compound I in a mixture of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanololeamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the formulation in water;
III. a solution of 20 parts by weight of a novel compound I in a mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the _ formulation in water;
IV. an aqueous dispersion of 20 parts by weight of a novel c~ ound I in a mixture of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction boiling within the range from 210 to 280 C and 10 part~ by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the formulation in water;
V. a mixture milled in a hammer mill and comprising 20 parts by weight of a novel c~...~o~nd I, 3 parts by weight of the sodium salt diisobutylnaphtalene-~-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor and 60 parts by .
~99~22 weight of silica gel powders; a spray liquor is obtained by finely distributing the mixture in water VI. a thorough mi~ture of 3 parts by weight of a novel compound I and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient;
VII. a thorough mixture of 30 parts by weight of a novel cG"~ound I, 92 parts by weight of silica gel powder and 8 parts by weight of liquid paraffin which was sprayed onto the surface of this silica gel; this formulation imparts good adhesive capability to the active ingredient;
15 VIII. a stable aqueous dispersion of 40 parts by weight of a novel co,..~ .d I, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which dispersion can be further diluted;
IX. a stable oily dispersion of 20 parts by weight of a novel c~ ound I, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil;
X. a mixture milled in a hammer mill and comprising 10 parts by weight of a novel ~v.. ~ound I, 4 parts by weight of the f- sodium salt of diisobutylnaphthalene-a-sulfonic acid, 20 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, 38 parts by weight o~ silica gel and 38 parts by weight of kaolin; a spray liquor which contains 0.1% by weight of the active ingredient is obtained by finely distributing the mixture in 10,000 parts by weight of water.
The co~ Gu..ds I are applied by treating the fungi or the seeds, 40 plants or materials to be protected from fungal attack or the soil where the fungicidal amount of the active ingredients.
Application is effected before or after infection of the materials, plants or seed by the fungi.
~ 2~99~2~
The application rates are from 0.02 to 3, preferably from 0.1 to 1, kg of active ingredient per ha, depending on the type of effect desired.
5 In the seed treatment, amounts of active ingredient are from 0.001 to 50, preferably from 0.01 to 10, g per kilogram of seed are generally required.
The application rate of active ingredient for controlling pests 10 under open air conditions i8 from 0.02 to 10, preferably from 0.1 to 2.0, kg/ha of active ingredient.
The compounds I, alone or in combination with herbicides or fungicides, may also be applied mixed together with further crop 15 protection agents, for ~mple with growth regulators, pesticides or bactericides. The miscibility with fertilizers or with mineral salt solutions which are used for el; mi nating nutrient and trace element deficiencies is also of interest.
20 The crop protection agents and fertilizers may be added to the novel compositions in a weight ratio of from 1:10 to 10:1, if desired also immediately before use (tank mix). Mixing with fungicides or insecticides often results in a broadening of the fungicidal action spectrum.
The followin~ list of fungicides together with which the novel co.,.~ounds may be applied is intended to illustrate the possible combinations but not to restrict them:
30 sulfur, dithiocarbamates and derivatives thereof, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc 35 (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate) and N,N'-polypropylenebis(thiocarbamoyl) disulfide; nitro derivatives, such as dinitro-(l-methylheptyl)-phenyl crotonate, 40 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate and diisopropyl 5-nitroisophthalate;
heterocyclic substances, such as 2-heptadecyl-2-imidazoline 45 acetate, 2,4-dichloro-6-(o-chloro~ n; 1 i ~o ) -8-triazine, O,0-diethyl phth~l;midophosphonothioate, 5-a-mino-~ [bis-(dimethylamino) phosphinyl]-3-phenyl-1,2,4-triazol, 2,3-dicyano-1,4-dithio-2~99122 519anthraquinone, 2-thio-1,3-dithiolo-~-[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonyl-aminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydro-5 phthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-10 3-methyl-5-isoxazolone, 2-thiopyridine l-oxide, 8-hyd~uxy~inoline and its copper ~alt, 2,3-dihydro-5-carbox~n~l;do-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboYAn;l;do-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carbo~n;l;de, 2-methylfuran-15 3-carbox~n;l;de~ 2,5-dimethylfuran-3-carbox~n;l;de, 2,4,5-trimethylfuran-3-carbo~An~l;de, N-cyclohexyl-2,5-dimethyl-furan-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine 2,2,2-trichloroethylacetal, 20 piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)-formamide, 1-(3,4-dichloro~n;l;no)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and it~ salts, 2,6-dimethyl-N-cyclodedecylmorpholine and its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-25 2,6-dimethylmorpholine, N-t3-(p-tert-butylphenyl)-2-methyl-propyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, 1-t2-(2,4-dichloro-phenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea, 30 1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanone, 1-~4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanol, ~-(2-chlorophenyl)-a-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-me~hyl-pyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis-35 (3-ethoxycarbonyl-2-thioureido)benzene and 1,2-bis(3-methoxy-carbonyl-2-thioureido)-benzene~
and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide, 40 hexachlorobenzene, methyl DL-N-(2,6-dimethylphenyl)-N-furoylalaninate, methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxy-acetyl)-alaninate, N-(2,6-dimethylphenyl)-N-chloro-acetyl-D, L-2-aminobutyrolactone, methyl DL-N-(2,6-dimethyl-phenyl)-N-(phenylacetyl)-alaninate, 5-methyl-5-vinyl-3-(3,5-45 dichloro-phenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichloro-phenyl]-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, ~1~9~22 N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-~N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-lH-1,2,4-triazole, 2,4-difluoro-a-(lH-1,2,4-triazol-1-ylmethyl)-5 benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine and l-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-lH-l~2~4-tria2ole.
Synthesis Examples ~he methods described in the synthesis ~mples below were used for obt~in;ng further c~,upG~..ds I, with appropriate modification of the starting compounds. The compounds thus obtained are shown in the subsequent table together with physical data.
Example 1 Methyl a-methoxy-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~" CH(OCH3)--C02CH3 CH20-(2-CH3-C6Hs) 25 1.1 0.5 g of sodium borohydride was added a little at a time to 14.2 g of methyl ~-t2-(2-methylphenG~y ~~hylene)-phenyl]-~-ketoacetate in 110 ml of methanol while cooling at -20 C. After one hour at -15 C, the mixture was allowed to warm up to 0 C, and a total of 18.5 g of 7%
strength hydrochloric acid were added dropwise to the reaction mixture. The mixture thus obtained was substantially freed from the ~olvent under redu~ed preYsure. The residue obtained wa~ taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 14.2 g of methyl a-hydroxy-~-~2-(2t-methylphenoxymethylene)phenylacetate were obtained as an oil [IR (cm~l)s 1740, 1496, 1454, 1438, 1242, 1190, 1122, 1075, 1052, 752].
, 40 1.2 A solution of 2.86 g of the product from 1.1 in 30 ml of dimethylfor~- ;de was added dropwise at 0 C to a mixture of 0.26 g of sodium hydride and 10 ml of dimethylformamide. The mixture thus obtained was heated at about 3~ C for 10 minutes in an ultrasonic bath, a clear solution forming. 2.84 g of methyl iodide in 10 ml ~ ~19~22 of dimethylformamide were added to this solution at about 25-C.
After about 12 hours, the mixture was taken up with 300 ml of dilute sodium chloride solution. After extraction with tert-butyl methyl ether, working up of the organic phase and flash chromatography tS:l cyclohexane/tert-butyl methyl ether], 1 g of the target c~ ound was obtained [IR (cm~1): 1753, 14g6, 1461, 1453, 1436, 1241, 1193, 1121, 1013, 751].
Example 2 Methyl ~-methoxy-a-{2-t2-methyl-4-(1-methoximinoethyl)-phenoxymethylene]-phenyl}acetate (E) ~" CH(OCH3)--CO2CH3 ~ CH2O ~ C(CH3)=NOCH3 2.1 8.6 g of methyl a-hydroxy-~-[2-methoxymethylenephenyl]
acetate were obtained from 10.4 g of methyl a-t2-methoxymethylenephenyl]-a-ketoacetate and 0.5 g of sodium borohydride in 100 ml of diethylene glycol dimethyl ether by a method s~m~ 1 ~r to that described in 1.1 tlH-NMR (ppm): 3.35(s,3H); 3.75(s,3H); 4.11(d,1H)j 4.55(AB,2H); 5.42(d,1H); 7.25-7.4(m,4H)].
2.2 3.9 g of methyl ~-methoxy-a-t2-methoxymethylenephenyl]-acetate were obtained from 6.1 g of the product from 2.1 and 8.2 g of methyl iodide in a total of 110 ml of dimethylformamide by methods similar to that described in 1.2 [IR (cm~l): 1752, 1452, 1436, 1195, 1172, 1113, 1102, 1013, 752].
2.3 4 g of hydrogen bromide were added to 4.9 g of the product from 2.2 in 65 ml of methylene chloride at from -5 C to 0 C. After 12 hours at 0 C, the solvent was removed at reduced pressure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 5.4 g of methyl a-methoxy-~-[2-bromomethylphenyl]acetate were 2~g9il22 obtained [IR (cm~l): 1753, 1435, 1273, 1195, 1171, 1109, 1012, 762].
2.4 A mixture of 0.63 g of 2-methyl-4-(1-methoxyimino-ethyl)phenol, 0.96 g of the product from 2.3, 7.3 g of potassium carbonate and 25 ml of dimethylformamide was stirred for 2 hours at 50 C. After 12 hours at about 25 C, the solvent was removed at reduced pressure. The residue was taken up in tert-butyl methyl ehter. After purifying the organic phase with water, drying and evaporating down, 1 g of the target compound (mp.
76-78 C) was obtained.
Example 3 lS Methyl a-methoxy-a-{2-([1'-(4"-Chlorophenyl)-1'-methyl]iminoxy-methyl)phenyl}acetate (E) ~" CH~OCH3)--CO2CH3 ~ fi~
CH20N=C(CH3) ~ Cl 0.6 g of the target compound was obtained from 0.7 g of 25 4-chloroacetophenone oxime, 1.0 g of the product from 2.3, 0.1 g of sodium hydride and a total of 20 ml of dimethylformamide by methods si~ilar to that described in 2.4 tIR (cm~l): 1753, 1491, 1195, 1172, 1114, 1097, 1013, 929, 830, 755].
30 Example 4 Ethyl a-ethoxy-a-~2-(2-methylphenoxymethylene)phenyl]acetate 3~ ~ C~(OC~C 3)CO2C~zC~3 E~3C
4.1 Carbon tetrabromide was added a little at a time to a mixture of 6 g of the product from 1.1 and 60 ml of acetonitrile at O C. After lS minutes at O C, 6 g of triphenylphosphine were added. After 12 hours at 25 C, the reaction mixture was filtered. Evaporating down the filtrate gave the crude product, which was purified by means of flash chromatography ~10:1 cyclohexane/
~99~22 tert-butyl methyl ether]. 5.7 g of methyl ~-bromo-a-[2-(2-methylphenoxymethylene)phenyllacetate were obtained (mp. 79-81 C).
5 4.2 A mixture of 1.18 g of sodium ethylate in 2.57 g of ethanol was added to a mixturè of 5.2 g of the product from 4.1 and 35 ml of ethanol at about 25 C. After 2 hours at 60 C, the reaction mixture was freed from solvent at reduced pressure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 2.4 g of the target compound were obtained [1H-NMR (~/ppm):
11-13(m,6H); 2.25(s,3H); 3.4-3.65(m,2H); 5.18(s,1H);
5.25(AB,2H); 6.8-7.6(M,8H)].
Example 5 Methyl a-methoxy-a-t2-(2-methylphenoxymethylene)phenyl]acetamide ~ CH(OCH3)-C(=O)-NHCH3 ~ CHzO
3.9 g of a 40 percent strength aqeous methylamine solution were added to a mixture of 1.5 g of the product from 1.2 and 15 ml of tetrahydrofuran at 25 C. After 6 hours at 70 C, the reaction 30 mixture was freed from the solvent at reduced prQssure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 1.2 g of the target compound were obtained (mp. 70 - 71 C).
35 F~mple 6 Methyl a-ethylamino-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~ H~NHCzHs)-C(=O)-OCH3 524 ~99~2~
1.1 g of a 70 percent strength a~ueous methylamine solution were added to a mixture of 1.9 g of the product from 4.1 and 20 ml of tetrahydrofuran at 25 C. After 2 hours at 50 C, the reaction mixture was freed from the solvent at reduced pressure. The 5 residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 1.7 g of the target compound were obtained tIR (cm~l: 1738, 1496, 1462, 1453, 1435, 1240, 1206, 1161, 1122, 7511.
10 Example 7 Methyl a-methoxyamino-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~,,CH(NHoCH3j-Co2cH3 2.4 g of sodium hydroxide were added to a mixture of 5 g of methoxyamine hydrochloride and 50 ml of water at 5 C. After 10 minutes, a mixture of 4.2 g of the product from 4.1 and 50 ml of 25 tetrahydrofuran was added to this mixture at 5 C. After 2 hours at 50-C, a mixture of 5 g of methoxyamine hydrochloride, 50 ml of water and 2.4 g of sodium hydroxide was added to the reaction mixture. After 24 hours at 70 C, the reaction mixture was freed from the solvent at reduced pressure. The residue was taken up in 30 tert-butyl methyl ether. After purifying the organic phase with water, drying, evaporating down and flash chromatography t5:1 cyclohexane/tert-butyl methyl ether], 2.5 g of the target cu.,l~ound were obtained (mp. 60-62 C).
35 Example 8 Methyl a-methoxyamino-a- -~2-(2-methylphenoxymethylene)phenyl]acetate ~" CH(SCH3)-CO2cH3 ~ g3~2~
A mixture of 1.9 g of the product from 4.1, 0.43 g of sodium thiomethylate and 20 ml of dimethylformamide were stirred for 4 hours at 25 C. The reaction mixture was then freed from the solvent at reduced pressure. The residue was taken up in 5 tert-butyl methyl ether. After purifying the organic phase with water, drying, evaporating down and flash chromatography [5:1 cyclohexane/tert-butyl methyl ether], 0.6 g of the target compound was obtained (mp. 64-66 C).
o Table N
,~ CH ( UR ' )--COVR' ' ~
Xn~l~ Y ~--A ' ( I ' ) No. UR' VRn XnY' A' Physical data OCH3 OCH3 HCH2O 2-CH3-C6H4 1753, 1496, 1461, 1453, 1436, 1241, 1193, 1121, 1013, 751 2 OCH3 OCH3 HCH2O 2,5~CH3)2-C6H3 1753, 1509, 1453, 1261,ll9S, 1172, 1155, ~"
1129, 1116, 1017 3 OCH3 OCH3 HCH2O 2~4~cH3)2 C6H3 1753, 1504, 1253, l~l, 1196, 1172, 1133, 1116, 1013, 751 4 OCH3 OCH3 HCH2O 2-CH3~-CH(CH3)2-C6H3 1754, 1512, 1455, 1251, 1195, 1178, 1117, S OCH3 OCH3 HCH20 2-CH3-4-[C(CH3)=NOCH33-C6H3(E3 76- 78 6 OCH3 OCH3 HCH2O 2-CH3-4-[C(CH3)=NOC2H5]-C6H3(E) 1753, 1506, 1277, 1242, 1193, 1143, 1094, 1051, 1012 7 OCH3 OCH3 ' HCH2O 2~s-(cH3)2-4-[c(cH3)=Noc2H53-c6H2(E) 1753, 1510, 1327, 1245,ll9S, 1147, 1117, 2 1092, 1046, 1011 No. UR' -VR" XnY' A' Physicaldata o 8 OCH3 OCH3 HCH2O 2-n-C3H7-6-CF3-pyrimidin-4-yl 1755, 1599, 1572, 1421, 1352, 1185, 1151, ~
1121, 1091, 1017 9 OCH3 OCH3 HCH2O l-C6Hs-pyrazol-3-yl 1751, 1600, 1545, 1507, 1480, 1464, 1358, 1195, 1115, ?55 OCH3 OCH3 HCH2O 1~4-CH3-C6H4)-pyrazol-3-yl 1752, 1544, 1519, 1483, 1453, 1359, 1195, 1115, 1097, 746 11 OCH3 OCH3 HCH2O 1~4-CI-C6H4)-pyrazol-3-yl 1752, 1546, 1503, 1481, 1358, 1195, 1115, 1094, 936, 749 12 OCH3 OCH3 HCH2O 1~2,~CI2-C6H3)-pyrazol-3-yl 1753, 1547, 1496, 1474, 1357, 1195; 1110, 1057, 1020, 747 13 OCH3 OCH3 HCH2O (4-CI-C6H4)-C(CH3)=N(E) 1753, 1491, 1195, 1172, 1114, 1097, 1013, u 929, 830, 755 14 OCH3 OCH3 HCH2O (3,5-CI2-C6H3) C(CH3)=N(E) 1753, 1558, 1304, 1195, 1172, 1115, 1098, 1016, 995, 801 OCH3 OCH3 HCH2O (3-CF3-C6H4)-C(CH3)=N(E) 1753, 1341, 1298, 1276, 1195, 1168, 1124, 1100, 1072, 1016 16 OCH3 OCH3 HCH2O (4-CF3-C6H43-C(CH3)=N(E) 1753, 1328, 1195, 1169, 1116, 1099, 1065, 1014, 844, 745 17 OCH3 OCH3 HCH2O (4-cH3-c6H4)-c(cH3)=N(E) 1753, 1452, 1368, 1195, 1172, 1115, 1099, 1015, 926, 818 18 OCH3 OCH3 HCH20 (3-CI-C6H4)-C(CH3)=N (E) 1752, 1195, li72, 1115, 1098, 1015, 998, 786, 756, 688 ~
NO. UR' VR" XDY' A' Physical data ~n 19 OCH3 OCH3 HCH2O CH3 1752, 1452, 1436, 1195, 1172, 1113, 1102, ~
1013, 752 n OCH3 OCH3 H _ CH2Br 1752, 1435, 1273, 1215, 1195, 1171, 1109, n 1012, 762 21 OCH3 OCH3 HCH2O 1~5-CF3-pyrid-2-yl)-pyrazol-3-yl 1754, 1609, 1553, 1501, 1431, 1358, 1326, 1164, 1126, 1089 22 OCH3 OCH3 HCH20 1-(5-CF3-pyrid-2-yl)~CI-pyrazol-3-yl 84- 85 23 OCH3 OCH3 HCH20 4~4-CI-C6H4)-thi~ol-2-yl 82- 83 24 OCH3 OCH3 H CH2 4~4-CI-C6H4)-thiazolin-2-on-3-yl 145-150 OCH3 OCH3 HCHzO 4~2,~CIz-C6H3)-thiazol-2-yl 1753, 1530, 1465, 1305, 1253, l~s, 1195, u 1173, 1110,751 26 OCH3 OCH3 H CH2 4~2,4-CI2-C6H3tthi~7nli~ 2-on-3-yl 1751, 1662, 1602, 1471, 1453, 1435, 1215, 1195, 1176, 1102 27 OCH3 OCH3 HCH2O 3-CH3~[C(CH3)=NOC2Hs]-C6H3(E) 1753, 1605, 1503, 1240, 1195, 1170, 1116, 1092, 1048, 1014 28 OCH3 OCH3 HCH2O 2-CI-5-CH3~lC(C2H5)=NO-n-C3H~l-C6H2 1753, 1499, 1251, 1196, 1171, 1116, 1105, 1052, 1019 29 OCH3 OCH3 HCH20 2,5-CI2-4-[C(C2Hs)=NOC2Hs]-C6H2 (E) 1753, 1487, 1252, 1230, 1196, 1116, 1082, 1051, 1008, 750 ~:' No. UR' VR" XnY' A' Physical data o 30 OCH3 OCH3 HCH2O H3CON=C(CH3)C(CH3)=N (E);(E) 1.99(3H,s); 2.Q4(3H,s);3.39(3H,s); ~
3.72(3H,s); 3.92(3H,s); 5.17(1H,s); - u~
5.32(2H,AB); 7.3-7.55(4H,m) O
Table 900 Compounds of the general formula I.B (n - O) in which UR' i8 ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each 35 c~ Gu,ld to the substituents stated in a line of Table H
Table 901 Compounds of the general formula I.B (n = O) in which UR' is 40 methoxy, VR~ is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each cGr..~l~d to the substituents stated in a line of Table H
219~2~
Table 902 Cv,,,~unds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this 5 pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 903 Cor.,~ounds of the general formula I.B (n 5 O) in which UR' is methylamino,.VR" is methoxy, yb is oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 1~ corresponding for each ~..~ound to the substituents stated in a ( line of Table H
Table 904 20 C~..-~Gunds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each co~ ou.ld to the substituents stated in a line of Table H
Table 905 Co~ ou~lds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidln-4-yl, 30 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy ( group in the 6 position and the R~ group corresponding for each c~ oulld to the substituents stated in a line of Table H
Table 906 Co~ Gu-lds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is ethoxy, yb iS oxygen and Ab is~ pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group correspondlng for each 40 cv..*~und to the substituents stated in a line of Table H
Table 907 Compounds of the general formula I.~ (n = 0) in which UR' is 45 methoxy, VR" is methylamino, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 0050/45~04 corresponding for each compound to the substituents stated in a line of Table H
Table 908 Co".~ul.ds of the general formula I.B (n = 0) in which UR' is ethoxy, VRn i8 methylamino, yb is oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each 10 ~ und to the substituents stated in a line of Table H
Table 909 Compounds of the general formula I.B (n = 0) in which UR' is 15 methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each co...~ound to the substituents stated in a line of Table H
20 Table 910 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy 25 group in the 6 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 911 30 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each c~.~.~ound to the substituents stated in a line of Table H
Table 912 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 40 this pyri~idin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 913 Compounds of the general formula I.B (n = 0) in which UR' i5 methoxy, VR" is ethoxy, yb iS oxygen ~nd Ab is pyrimidin-4-yl, 5 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 914 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" is etho~y, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each co,..p~ulld to 15 the substituents stated in a line of Table H
Table 915 Compounds of the general formula I.B (n = 0) in which UR' is 20 methylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 916 C~...po~nds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, 30 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each cv.~.pound to the substituents stated in a line of Table H
Table 917 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is ethoxy, yb is oxygen and Ab is~pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each 40 col"~ound to the substituents stated in a line of Table H
Table 918 Compounds of the general formula I.B (n = o) in which UR' is 45 ethylamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy OOS0/45~04 2~9g~22 group in the 2 position and the R~ group corresponding for each co.,.~o~nd to the substituents stated in a line of Table H
Table 919 Co".~ounds of the general formula I.B (n - 0) in which UR' is methoxy, VR is methylamino, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group 10 corresponding for each cvA..~ou,~d to the substituents stated in a line of Table H
Table 920 15 Compounds of the general formula I.B (n = 0) in which UR' is ( ethoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 921 Compounds of the general formula I.B (n = 0) in which UR' i~
methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, 25 this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each cv~,lpuund to the substituents stated in a line of Table H
Table 922 ,- Co~ oullds of the general formula I.B (n = 0) in which UR~ is ethoxy, VR" i8 ethylamino, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each 35 compound to the substituents stated in a line of Table H
Table 923 Compounds of the general formula I.B (n = 0) in which UR' is 40 methoxy, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
4~
~199~22 Table 924 Compounds of the general formula I.B (n = 0) in which UR' i5 ethoxy, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, S this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 925 C~."~o~nds of the general formula I.B (n = 0) in which UR' is methoxy, VR" .i5 ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 15 c _und to the substituents stated in a line of Table H
f ~- Table 926 Co~ oucds of the general formula I.B (n - 0) in which UR' is 20 ethoxy, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
25 Table 927 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an 30 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a { line of Table H
Table 928 Co~ unds of the general formula I.B (n = o) in which UR' is ethylamino, VR~ is methoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 40 co~ nd to the substituents stated in a line of Table H
Table 929 Compounds of the general formula I.B (n = 0) in which UR' is 45 methylamino, VRn is ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy 267 2 1 9 ~ll2 2 group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 930 CGl.,pounds of the general formula I.B (n = 0) in which UR' is ethylamino, VRn is ethoxy, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 10 compound to the substituents stated in a line of Table H
Table 931 Compounds of the general formula I.B (n = 0) in which UR' is 15 methoxy, VRn is methylamino, yb iS oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each c~l..pGulld to the substituents stated in a line of Table H
Table 932 CGr..~G~nds of the general formula I.B (n - 0) in which UR' is ethoxy, VR" is methylamino, yb is oxygen and Ab is pyrimidin-2-yl, 25 this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each co..~Gund to the substituents stated in a line of Table H
Table 933 C~...po~,.ds of the general formula I.B (n - 0) in which UR' i8 methoxy, VR" is ethylamino, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each 35 co.,.pou..d to the substituents stated in a line of Table H
Table 934 CGl..pounds of the general formula I.B (n - 0) in which UR' is 40 ethoxy, VRn is ethylamino, yb i8 oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
2199~2 Table 935 Compounds of the general formula I.B (n = 0) in which UR' is methoxy, VR" is methoxy, yb iS oxygen and Ab i8 5 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group C~l esponding ~or each ~ .~ound to the substituents stated in a line of Table H
10 Table 936 Cv...~nds of the general formula I.B (n ~ 0) in which UR' is ethoxy, VR" is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy 15 group in the 4 position and the R~ group corresponding for each c~"lpoul~d to the substituents stated in a line of Table H
Table 937 20 C~.,*ounds of the general formula I.~ (n = 0) in which UR' is methoxy, VR" is ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 938 Compounds of the general formula I.B (n = 0) in which UR' is ethoxy, VR" i8 ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, 30 this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each f compound to the substituents stated in a line of Table H
Table 939 Compounds of the general formula I.B (n = 0) in which UR' is methylamino, VRn is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 40 corresponding for each cr Eound to the substituents stated in a line of Table H
Table 940 45 Compounds of the general formula I.B (n = 0) in which UR' is ethylamino, VR" is methoxy, yb is oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an u~ u~
~ 269 2199~22 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substituents stated in a line o~ Table H
5 Table 941 co"l~vu-ds of the general formula I.B (n ~ 0) in which UR' is methylamino, VR" is ethoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an 10 R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each ~ ou.ld to the substituents stated in a line of Table H
Table 942 C Compounds of the general form~ I.B (n 2 o~ in which UR' is ethylamino, VRn is ethoxy, yb i8 oxygen and ~b i8 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 20 corresponding for each ~u..l~ou.,d to the substituents stated in a line of Table H
Table 943 25 Compounds of the general for~ (n = 0) in which UR' is methoxy, VR" is methylamino, yb i8 oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each c~."~ourld to the substituents stated in a 30 line of Table H
f Table 944 Compounds of the general formula I.B (n = 0) in which UR' is 35 ethoxy, VR" is methylamino, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each compound to the substitue~ts stated in a line of Table H
Table 945 Compounds of the general formula I.~ (n = 0) in which UR' is methoxy, VR" is ethylamino, yb iS oxygen and Ab is 45 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 2~99~2 corresponding for each compound to the substituents stated in a line of Table H
Table 946 Compounds of the general formula I.B (n 2 0) in which ~R' is ethoxy, VR" is ethylamino, yb is oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 10 corresponding for each c~...po~nd to the substituents stated in a line of Table H
Table H
15 No. R~
3 2-Cl 4 3-Cl 2-Br 6 2-Cyano 7 3-Cyano 8 2-Isocyano 12 3-NH(CH3) 30 13 2-N(CH3)2 18 3-NH-CONH(C2Hs) 19 2-NH-SocH3 45 26 2-(2-F-C6H4O) ~U~/4~4 ~ 271 2199'122 No. R~
29 3-(4-CH3-C6S020) 34 2-S(O)CH3 39 3-COC6Hs 15 40 2-(E)-CH'NOH
( 41 3-(E)-CH=NOH
42 2-(E)-CH5NOCH3 43 2-(E)-C(CH3)=NOH
3-CONH(CH3) 47 2-CSNH(CH3) 3-C2Hs 52 2-CH2Br 30 53 2-CH2Cl f 54 2-CH2CN
40 61 2-CH=CH2 62 2-CH2-CH=CH2 63 2-C_CH
64 2-CH2_CH
3-CH2C(CH3)=CH2 2-OCH2CH=CH2 67 3-OCH2CH=CH2 ~ 2199~22 No. R~
69 3-c6H5 5 70 2-C6HsO
72 2-(4-Cl-C6H40) 74 2-OCH3, 3-OCH3 2-Cyano, 5-Cl 76 2-Cyano, 6-Cyano 77 2-F, 5-Cl 78 3-OCH3, 5-OCH3 15 79 2-No2, 3-OCH3 3-oCH2, 5-Cyano 84 2-i-C3H7 2-i-C3H70 86 2-F, 6-F
2-F, 3-F
88 2-n-C3Hp 89 2-n-C~HgO
2-CH(OH)CH3 91 2~t~CqHg 30 92 2-s-C4Hg r g3 2-n-C3H7 94 2-(E/Z)-CH=CH(CH3) 2-Cyano, 5-OCH3 35 96 2-Cyano, 5-N(C2Hs) 2 97 ~ 2-CONH2 98 2-C_CSi(CH3)3 99 2-F, 5-F
40 100 2-(E)-CH300C-C-CHOCH3 101 3-F, 5-F
106 2-Cyano, 6-F
~U50/452~4 ~ 219~'122 No. R~
107 2-NO2, 6-F
108 2-CSNH2, 6-F
S 109 2-Cyano, 3-F
110 2-Cyano, 5-F
111 2-Cyano, 3-OCH3 112 2-Cyano, 6-OCH3 113 2-NO2, 5-OCH3 114 2-NO2, 6-OCH3 115 2-CSNH2, 3-OCH3 116 2-CSNH2, 5-OCH3 117. 2-CSNH2, 6-OCH3 15 118 2-Cyano, 3-Cyano 119 2-F, 3-Cyano 120 .2-OCH3, 3-Cyano 121 3-Cyano, 6-F
20 122 2-Cyano, 6-Br 123 2-Cyano, 6-NO2 124 2-Cyano, 6-OC2Hs 125 2-Cyano, 6-CO2C2H5 25 126 2-Cyano, 6-CH3 127 2-Cyano, 5-CH2C6H5 129 2-C(CH3)=NOCH3 ~' 132 4-oc6H5 133 4-Cyano 35 135 4-(E)-CH=NOH
136 4-(E)-CH=NOCH3 137 4-(E)-C(CH3)=NOCH3 140 4-SO2(CH2)3CH3 142 2-F, 4-F
143 2-Cl, 4-Cl 144 2-NO2, 4-F
145 2-CN, 4-Cl ., 0050/45204 2 1 9 9 ~ 2 2 No. R~
146 2-CN, 4-Br 147 2-CN, 4-NO2 5 148 2-CN, 4-OCH3 149 2-CN, 4-OCF3 150 2-CN, 4-CN
151 2-CN, 4-COOCH3 152 3-CN, 4-F
153 2-CSNH2, 4-OCH3 154 2-NO2, 4-OCH3 Table 947 Co,..~o~llds of the general formula I.C (n - 0) in which UR' is methoxy, V-R" i8 methoxy, yc i8 CH=C(Cl)-C(=O)-O-# (-~ = bond to AC) and Ac for a cv,..~ou..d corresponds to a group of Table I.1 20 Table 948 C~ ou,lds of the general formula I.C (n = 0) in which UR' i~
ethoxy, VR" is methoxy, yc i~ CH=C(Cl)-C(=O)-O-# (-# = bond to AC) and Ac for a cvl..~oul.d corresponds to a group of Table I.l Table 949 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to AC) 30 and Ac for a compound corresponds to a group of Table I.l f Table 950 Compounds of the general formula I.C (n - 0) in which UR' i9 35 ethoxy, VR" is ethoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to Ae) and Ac for a compound corresponds to a group of Table I.l Table 951 40 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=O)-O-# (-# = bond to AC) and Ac for a cG,.,~ound corresponds to a group of Table I.1 U~5~
Table 952 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VRn is methoxy, yc is CH=C(Cl)-C(=0)-0-# (-~ = bond to 5 AC) and Ac for a c~ ound corresponds to a group of Table I.1 Table 953 CG...~uunds of the general formula I.C (n = 0) in which UR' i8 10 methylamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-o-# (-~ = bond to AC) and Ac for a cv...pou~ld corresponds to a group of Table I.l Table 954 15 Co...~uu--ds of the general formula I.C (n = 0) in which UR' is < ethylamino, VR" is ethoxy, yc is CH=C(C1)-C(=0)-0-# (-~ = bond to AC) and Ac for a co...~u~.d corresponds to a group of Table I.l Table 955 Cv...pounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH=c(cl)-c(=o)-o-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.l 25 Table 956 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methylamino, yc i8 CH=C(Cl)-C(=0)-0-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.l Table 957 C~...~ou..ds of the general formula I.C (n ~ 0) in which UR' is methoxy, VR is ethyla~ino, yc is CH=C(Cl)-C(=0)-0-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.1 Table 958 Compounds of the general formula I.C (n = 0) ~n which UR' is 40 ethoxy, VRn is ethylamino, yc is CH=C(Cl)-C(=0)-0-# t-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.l ~ 2199~22 Table 959 Cor,.A~o~Ads of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH~C~A~r)-C(-0)-O-~ (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 960 Cu...po~Ands of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" i8 methoxy, YQ i8 CH=C(A~r) - C(=o)-O-# (-# = bond to AC) and Ac for a compound co~responds to a group of Table I.1 Table 961 15 C~A.~ounds of the general formula I.C (n = 0) in which UR' is ~ methoxy, VR" i8 ethoxy, yc is CH=C(Br)-C(=O)-O-# (-~ = bond to AC) and Ac for a ~o...A~ound corresponds to a group of Table I.1 Table 962 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is ethoxy, yc is CH=C(Br)-C(=O)-O-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.1 25 Table 963 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(A~r)-C(=0)-O-# (-# = bond to AC) and Ac for a cG,.,A~ou.,d corresponds to a group of Table I.l Table 964 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C(Br)-C(=O)-O-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.1 Table 965 ~
Compounds of the general formula I.C (n = 0) in which UR' is 40 methylamino, VR" is ethoxy, yc is CH=C(A~r)-C(=O)-O-# (-# e bond to AC) and Ac for a cv~A..ApouA.d corresponds to a group of Table I.l ~S~/4~4 ~ 277 ~I99~22 Table 966 Co~ uullds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc is CH=C(Br)-C(=0)-O-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 967 Cu.-.~o~,,ds of the general formula I.C (n - 0) in which UR' is 10 methoxy, VRn is methylamino, yc is CH=C(Br)-C(=0)-O-# (-# = bond to AC) and Ac for a co,-,~nd corresponds to a group of Table I
Table 968 15 Compounds of the general formula I.C (n = O) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(Br)-C(=O)-O-# (-# = bond to AC) and Ac for a ~m~o~nd corresponds to a group of Table I.l Table 969 Compounds,of the general formula I.C (n - 0) in which UR' is methoxy, VR" i8 ethylamino, yc i8 CH=C(Br)-C(=0)-O-# (-# = bond to AC) and Ac for a ~v."poulld corresponds to a group of Table I.l 25 Table 970 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=c(Br)-c(=o)-o-# (-# 2 bond to AC) and Ac for a ~r..poulld corresponds to a group of Table I.l Table 971 ~.--Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-~ (-# - bond to AC) 35 and Ac for a c~ o~nd corresponds to a group of Table I.l Table 972 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR is methoxy, yc is CH=c(cN)-c(-o)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.1 278 2~99~22 Table 973 Compounds of the general formula I.C (n s 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(CN)-C(=0~-# (-# = bond to AC) S and Ac for a compound corresponds to a group of Table I.1 Table 974 Cv~ Gunds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yc i~ CH=C(CN)-C(=O)-~ = bond to AC) and Ac for a compound corresponds to a group of Table I..1 Table 975 lS Compounds of the general formula I.C (n - 0) in which UR' is methoxy, VR" i8 methoxy, yc is CH=c(cN)-c(~o)-o-# (-# = bond to AC) and Ac for a ~ ol-nd corresponds to a group of Table I.1 Table 976 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methoxy, Y~ i8 CH=C(CN)-C(=0)-0-# (-# = bond to AC) and Ac for a c~m~nd corresponds to a group of Table I.1 25 Table 977 Compounds of the general formula I.C (n = 0) in which UR' i~
methoxy, VR is ethoxy, yc is CH=C(CN)-C(=O)-O-# (-~ = bond to AC) and Ac for a cG".~oulld corresponds to a group of Table I.l r Table 978 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(CN)-C~=O)-O-# (-# = bond to AC) 35 and Ac for a compound corresponds to a group of Table I.l Table 979 Compounds of the general formula I.C (n = 0) in which UR' is 40 methylamino, VRn is methoxy, yc is CH=C(CN)-C(=O)-O-# (-# = bond to AC) and Ac for a cvl..pound corresponds to a group of Table I.l 0050/4~204 Table 980 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=c(cN)-c(=o)-o-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 981 Compounds of the general formula I.C (n = 0) in which UR' is 10 methylamino, VR" is ethoxy, yc is CH=C(CN)-C(sO)-0-# (-# = bond to AC) and Ac for a c~ po~nd corresponds to a group of Table I.1 Table 982 lS Compounds of the general formula I.C (n = 0) in which UR' i8 ethylamino, VRn is ethoxy, yc is CH=C(CN)-C~=0)-0-# (-~ 3 bond to ~~ AC) and Ac for a compound correspond~ to a group of Table I.l Table 983 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH=C(CN)-C(=0)-0-~ (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I
25 Table 984 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(CN)-C(=O)-O-# (-# = bond to AC) and Ac for a co,~nd corresponds to a group of Table I.l f Table 985 . .
Compounds of the general formula I.C (n - 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-O-~ (-# = bond to 35 AC) and Ac for a cor.pound corresponds to a group of Table I.l Table 986 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR" i8 ethylamino, yc i8 CH=C(CN)-C(=o)-0-# (-# - bond to AC) and Ac for a oo~ o~nd corresponds to a group of Table I.
0050~45204 ' ~ . 280 2199422 Table 987 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc i8 CH=C(N02)-C(=O)-O-# (-# = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 988 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VRn is methoxy, yc is CH=C(N02)-C(=0)-0-# (-~ = bond to AC) and Ac for a cv~ und corresponds to a group of Table I.1 Table 989 15 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethoxy, yc is CHsC(N02)-C(cO)-0-# (-~ = bond to '- AC) and Ac for a compound corresponds to a group of Table I.l Table 990 Co,ll~o~nds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-~ - bond to AC) and Ac for a corll~oul~d corresponds to a group of Table I.1 25 Table 991 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" i8 methoxy, yc is CH=C(N02)-C(=o)-o-# (-# = bond to AC) and Ac for a co~ Gund corresponds to a group of Table I.l Table 992 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, Y~ is CH=C(N02)-C(=O)-O-# (-# = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.l Table 993 Compounds of the general formula I.C (n c 0) in which UR' is 40 methylamino, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-# = bond to AC) and Ac for a c~..*o~nd corresponds to a group of Table I.l ~ 281 219~122 Table 994 CG~ oul.ds of the general formula I.C (n = 0) in which UR' i8 ethylamino, VR" is ethoxy, yc i8 CH=C(N02)-C(=O)-O-# t-* = bond to 5 AC) and Ac for a compound corresponds to a group of Table I.1 Table 995 Co...~ounds of the general formula I.C (n = 0) in which UR' is 10 methoxy, VR" is methylamino, YC is CH=C(N02)-C('O)-O-# (-~ = bond to AC) and Ac for a ~v..~ound corresponds to a group of Table I.1 Table 996 15 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(N02)-C(-0)-0-# (-# = bond to AC) and Ac for a co,.,~oul,d corresponds to a group of Table I.l Table 997 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc i8 CH=C(N02)-C(=O) - o_# (-# e bond to AC) and Ac for a co.~.~ound corresponds to a group of Table I.l 25 Table 998 Co...~oul,ds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(N02)-C(-0)-0-~ 3 bond to AC) and Aa for a ~-v,ll~Gund corresponds to a group of Table I.l r Table 999 Co,ll~o~.,ds of the general formula I.C (n = 0) in which UR' is methoxy, VR~ is methoxy, yc is CH=C(Cl)-C(=0)-NH-~ (-# = bond to ~5 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1000 Compounds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR" i8 methoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# - bond to AC) and Ac for a co~ ound corresponds to a group of Table I.2 282 ~199~22 Table 1001 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR~ i8 ethoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to 5 AC) and Aa for a compound corresponds to a group of Table I.2 Table 1002 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is ethoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I..2 Table 1003 15 Cv.,,pvunds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a cv",~o~-ld corresponds to a group of Table I.2 Table 1004 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=c(cl)-c(=v)-NH-# (-# = bond to AC) and Ac for a cv.,,po~nd corresponds to a group of Table I.2 25 Table 1005 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" is ethoxy, yc is CHGC(Cl)-C(=0)-NH-# (-# = bond to AC) and Ac for a cvl"~o~nd corresponds to a group of Table I.2 Table 1006 Compounds of the general formula I.C (n s 0) in which UR' is ethylamino, VR" i8 ethoxy, yc is CH=C(Cl)-C(=0)-NH-~ (-# e bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1007 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxy, VR is methylamino, yc is CH=C(Cl)-C(=o)-NH-# (-# ~ bond to AC) and Ac for a cv...~ound corresponds to a group of Table I.2 ':
~5~/45~4 -283 21g9 122 Table 1008 Compounds of the general formula I.C (n - 0) in which UR' i~
ethoxy, VR~' is ~ethylamino, yc is CH=C(Cl)-C(-O)-NH-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1009 Compounds of the general formula I-C (n 3 O) in which UR' is 10 methoxy, VR" is ethylamino, yc is CH-C(Cl)-C(-O)-NH-# (-# = bond to AC) and Ac for a ~o,..~ound corresponds to a group of Table I.2 Table 1010 15 Compounds of the general formula I.C (n - 0) in which UR' is ethoxy, VR" is ethylamino, yc i8 CH-C(Cl)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1011 Compo~nds of the general formula I.C (n ~ O) in which UR' i8 methoxy, VR" is methoxy, yc is CH=C(Br)-C(=O)-NH-# (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 25 Table 1012 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR i5 methoxy, yc is CH=C(Br)-C(=O)-NH~ - bond to AC) and Ac for a cG.,.poulld corresponds to a group of Table I.2 Table 1013 Compounds of the general formula I.C (n = 0) in which UR' i8 methoxy, VR" is ethoxy, yc is CH=C(Br)-C(=O)-NH-# (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1014 C~ oul,ds of the general formula I.C (n = 0) in which UR' is 40 ethoxy, VR is ethoxy, yc is CH3C(Br)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 -284 ~199~22 Table 1015 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VR" i8 methoxy, yc is CH=c(Br)-ct=o)-NH-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1016 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethylamino, VR" i8 methoxy, yc is CH--C(Br)-C(=0)-NH~ # = bond to A~) and Ac for a cv...pound corresponds to a group of Table I.2 Table 1017 15 Compounds of the general formula I.C (n s 0) in which UR' is f methylamino, VR" is ethoxy, yc is CH=C(Br)-C(=0)-NH-# (-~ 5 bond to AC) and Ac for a c~ o~"d corresponds to a group of Table I.2 Table 1018 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc i8 CH=c(Br)-c(=o)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1119 Co~ ou,lds of the general formula I.C (n = 0) in which UR' is ~ methoxy, VRn i8 methylamino, yc is CH-C(Br)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 f~ Table 1020 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methylamlno, yc is CH-C(Br)-C(=0)-NH-# (-~ = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1021 Co...~Gunds of the general formula I.C (n = 0) in which UR' i~
40 methoxy, VRn i8 ethylamino, yc i8 CH=C(Br)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I
O0~0/45204 ~ 285 2199122 Table 1022 Compounds of the general formula I.C (n = ~) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(Br)-C(20)-NH-$ (-~ = bond to AC) and Ac for a cv,.~ound corresponds to a group of Table I.2 Table 1023 Co..,~ounds of the general formula I.C (n = 0) in which UR' is 10 methoxy, VRn i8 methoxy, yc is CH=C(CN)-C(=O)-NH-# (-# 3 bond to AC) and Ac for a co,.,pou-~d corresponds to a group of Table I.2 Table 1024 15 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methoxy, yc i8 CH=C(CN)-C(=O)-NH-# (-# ~ bond to AC) and Ac for a cv..~oul~d corresponds to a group of Table I.2 Table 1025 ~0 Col"p~unds of the general formula I.C (n ~ 0) in which UR' is methoxy, VRn is ethoxy, yc is CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1026 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethoxy, yc i8 CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~- Table 1027 . . . = .
Co.~,~Gunds of the general formula I.C (n - 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(CN)-C(=O)-NH-# (-# ~ bond 35 to AC) and Ac for a co..,~o~.d corresponds to a group of Table I.2 Table 1028 ~
Compounds of the general formula I.C (n = 0) in which UR' is 40 ethylamino, VR" is methoxy, yc is CHsC(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 ~5~/45~4 - - -~ 286 2~99~1~2 Table 1029 Compounds of the general formula I.C (n = 0) in which UR' i9 methylamino, VR" is ethoxy, yc i8 CH=c(cN)-c(=o)-NH-# (-~ = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1030 Compounds of the general formula I.C (n - 0) in which UR' is lO ethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=O)-NH-~ = bond to AC) and Ac for a cv~ ound corresponds to a group of Table I.2 Table 1031 15 C~".~ou-~ds of the general formula I.C (n = 0) in which UR' is { methoxy, VRn is methylamino, yc is CH=C(CN)-C(=O)-NH-# (-~ = bond to AC) and Ac for a co.l.~ou.-d corresponds to a group of Table I.2 Table 1032 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=c(cN)-c(=o)-NH-# ~ bond to AC) and Ac for a cv...~ound corresponds to a group of Table I
25 Table 1033 C~,.~oullds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-NH-# (-# = bond to AC) and Ac for a o...~oulld corresponds to a group of Table I.2 f~ Table 1034 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-NH-$ (-# = bond to 35 AC) and Ac for a compound corresponds to a group of Table I.2 Table 1035 Compounds of the general formula I.C (n = o) in which UR' is 40 methoxy, VR" is methoxy, yc is CH=C(NO2)-C(=O)-NH-~ bond to AC) and Ac for a co..,pGund corresponds to a group of Table I.2 -287 219912~
Table 1036 Co~ ounds of the general formula I.C (n z 0) in which UR~ is ethoxy, VR" is methoxy, yc is CH=C(N02)-C(-0)-NH-# (-# 2 bond to 5 AC) and Ac for a compound corresponds to a group of.Table I.2 Table 1037 Compounds of the general formula I.C (n = 0) in which UR' i~
10 methoxy, VR" is ethoxy, yc is CH~C(No2)-c(=o)-NH-$ (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1038 15 Compounds of the general formula I.C (n 5 O) in which UR' is ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(G0)-NH-# (-~ = bond to AC) and Ac for a cor,.~oulld corresponds to a group of Table I.2 Table 1039 Compounds of the general formula I.C (n = 0) in which UR' i8 methylamino, VR" is methoxy, yc i8 CH-C(N02)-C(=0)-NH-~ bond to AC) and Ac for a ~l.*~u~.d correspond~ to a group of Table I.2 25 Table 1040 Compounds of the general ~ormula I.C (n - 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C(N02)-C(=0)-NH-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 . Table 1041 Compounds of the general formula I.C (n ~ 0) in which UR' is methylamino, VR" is ethoxy, yc i8 CHeC(NO2)-C(=O)-NH-# (-# = bond 35 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1042 Compounds of the general formula I.C (n - 0) in which UR' i5 40 ethyla~ino, VRn iS ethoxy, yc is CHsC(N02)-C(=O)-NH-~ = bond to AC) and Ac for a co~ o~lld corresponds to a group of Table I.2 ~ 288 ?199 1~2 ~able 1043 Compounds of the general formula I.C (n s 0) in which UR' is methoxy, VR" is methylamino, yc is CH2C~No2)-C(eO)-NH-# (-# 5 bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1044 Compounds of the general formula I.C (n = 0) in which UR' is 10 ethoxy, VR" is methylamino, yc is CH=C(N02)-C(sO)-NH-# (-~ = bond to AC) and Ac for a co~.,p~ld corresponds to a group of Table I.2 .
Table 1045 15 Compounds of the general formula I.C (n = o) in which UR' is methoxy, VR" is ethylamino, yc is CH=c(No2)-c(=o)-NH-# (-~ = bond to AC) and Ac for a cG.,*ound corresponds to a group of Table I.2 Table 1046 Co,-~u~lds of the general formula I.C (n ~ 0) in which UR' is ethoxy, VR" i8 ethylamino, yc is CH=C(N02)-C(=0)-NH-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 25 Table 1047 Compounds of the general formula I.C (n = 0) in which UR~ is methoxy, VR" is methoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-# = bond to AC) and Ac for a co...~ound corresponds to a group of Table I.2 f_ Table 1048 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methoxy, yc is CH=C(Cl)-c(=o)-N(CH3)-# (-# 5 bond 35 to AC) and Ac for a cn.~_und corresponds to a group of Table I.2 Table 1049 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxy, VR~' is ethoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 289 2199~22 Table 1050 Compounds of the general formula I.C (n - 0) in whieh UR' is ethoxy, VR" is ethoxy, yc is CH=c(cl)-c(=o)-N(cH3)-# (-~ = bond to 5 AC) and Ac for a eompound eorresponds to a group of Table I.2 Table 1051 Compounds of the general formula I.C (n = 0) in whieh UR' i8 10 methylamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a oo..~o~nd eorresponds to a group of Table I.2 Table 1052 Compounds of the general formula I.C (n 2 O) in whieh UR' is ethylamino, VR" is methoxy, yc i8 CH2C(Cl)-C(=O) -N(CH3)-# (-# =
bond to AC) and Ac for a ev~-~ound eorresponds to a group of Table I.2 Table 1053 Co..,pounds of the general formula I.C (n - 0) in whieh UR' is methylamino, VR" i~ ethoxy, yc is CH=C(Cl)-C(=O)-N(CH3)-~ (-# =
25 bond to AC) and Ac for a evl..pound eorresponds to a group of Table I.2 Table 1054 30 Cor..pGunds of the general formula I.C (n - 0) in whieh UR' is r ethylamino, VR" is ethoxy, yc is CH=C(Cl)-C(=O)-N(CH3)-~ (-# =
bond to AC) and Ac for a eompound eorresponds to a group of Table I.2 35 Table 1055 Compounds of the general formula I.C (n = 0) in whieh UR' is methoxy, VR" is methylamino, yc is CH=C(Cl)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a eor,.~und eorresponds to a group of Table 40 I.2 Table 1056 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methylamino, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
5 bond to A~) and Ac for a compound corresponds to a group of Table I.2 Table 1057 10 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a co...~ur.d corresponds to a group of Table I.2 15 Table 1058 co...~unds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 ethylamino, yc is CHsC(Cl)-C(=O)-N(CH3)-# (-# =
bond to AC) and Ac for a ~ und corresponds to a group of Table 20 I.2 Table 1059 Compounds of the general formula I.C (n - 0) in which UR' i8 25 methoxy, VR" is methoxy, yc is CH2C(Br)-C(=O)-N~CH3)-# (-# = bond to AC) and Ac for a ~v...~ou,ld corresponds to a group of Table I.2 Table 1060 30 C~,..pounds of the general formula I.C (n = 0) in which UR' is ~- ethoxy, VR" is methoxy, yc -~s CH=C(Br)-C(=0)-N(CH3)-# (-~ = bond to AC) and Ac for a co...~ul~d corresponds to a group of Table I.2 Table 1061 Co~.~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethoxy, yc is CH=C( Br)-C(=0)- N(CH3) -# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.2 40 Table 1062 Co...~ou~lds of the general formula I.C (n = 0) in which UR' iY
ethoxy, VR" is ethoxy, yc is CH=c(Br)-c(=o)-N(cH3)-# (-# = ~ond to AC) and A~ for a compound corresponds to a group of Table I.2 ~ 291 2199~22 Table 1063 Compounds of the general formula I.C (n - 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(~r)-C(=0) - N ( CH3 ) -# ( -# =
5 bond to AC~ and Ac for a compound corresponds to a group of Table I.2 Table 1064 10 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CH=C( Br)-C(=0) -N(CH3)--# (-# =
bond to AC) and Ac for a c~ ound corresponds to a group of Table I.2 15 Table 1065 ~' Compounds of the general formula I.C (n = 0) in which UR' is methylamino, VRn is ethoxy, yc is CH=C(Br)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a cv..*~u~ld corresponds to a group of Table 20 I.2 Table 1066 CG~ o~nds of the general formula I.C (n = 0) in which UR' is 25 ethylamino, VR" i5 ethoxy, yc is CH=C(Br)-C(=0)-N(CH3)-~bond to AC) and Ac for a c. oul~d corresponds to a group of Table I.2 Table 1067 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methylamino, yc is CH-C(Br)-C(=O) - N(CH3)-~ ( - # -bond to A~) and Ac for a c_ ound corresponds to a group of Table I.2 Table 1068 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" i8 methylamino, yc is CH=C (3r)-C(=0)-N(CH3)-# (-$ =
40 bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~ 292 2 1 9 9 ~ 2 2 Table 1069 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(Br)-C(=0)-N(CH3)-# (-# =
5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1070 10 CG~.pounds of the general formula I.C (n = 0) in which UR' is ethoxy, VRn is ethylamino, yc is CH=C(Br)-C(=0)-N(CH3)-#. (-# =
bond to AC) and Ac for a c~".~vund corresponds to a group of Table I.2 15 Table 1071 r ~-- C~."~oul~ds of the general formula I.C (n = 0) in which UR' is ~ethoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# = bond to AC) and Ac for a col"~o~.d corresponds to a group of Table I.2 Table 1072 Compounds of the general formula I.C (n = 0) in which UR' is ethoxy, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-~ (-# = bond 25 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1073 CG11~Ur1dS of the general formula I.C (n = 0) in which UR' is 30 methoxy, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# = bond _. to AC) and Ac for a cG.. ~o~l~d corresponds to a group of Table I.2 Table 1074 35 Compounds of the general formula I.C tn = 0) in which UR' is ethoxy, VR is ethoxy, yc is CH=c(cN)-c(=o)-N(cH3)-# (-~ 2 bond to AC) and Ac for a co...~o~-d corresponds to a group of Table I.2 Table 1075 Compounds of the general formula I.C (n ~ 0) in which UR' is methylamino, VR" is methoxy, yc is CH=C(CN)-C(-0)-N(CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 293 2199~22 Table 1076 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is methoxy, yc is CHsC(CN)-C(=0)-N(CH3)-~
5 bond to AC) and A~ for a compound corresponds to a group of Table I.2 Table 1077 10 Compounds of the general formula I.C (n = 0) in which UR' ismethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a co~ ound corresponds to a group of Table I.2 15 Table 1078 ( Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table 20 I.2 Table 1079 Co.,.pounds of the general formula I.C (n = 0) in which UR' is 25 methoxy, VR" is methylamino, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1080 Co",~ou~lds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is methylamino, yc is CH=C(CN)-C(=O)-N(CH3)-~ 3 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1081 Compounds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is ethylamino, yc is CH=C(CN)-C(=O)-N(CH3)-~ (-# =
40 bond to AC) and Ac for a compound corresponds to a group of Table I.2 -0050/452~4 ~ 294 2199~22 Table 1082 Co"l~o~nds of the general formula I.C (n 5 0) in which UR' is ethoxy, VR" is ethylamino, yc i~ CH=CtCN)-C(=O)-N(CH3)-# ~-# 5 5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1083 10 C~."~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" is methoxy, yc is CH=C(N02)-C( 50)-N(CH3)-~ t-# = bond to AC) and AC.for a compound corresponds ~o a group of Table I.2 Table 1084 lS
( Com~ounds of the general formula I.C (n - 0) in which UR' is - ethoxy, VR" is methoxy, yc is CH=C(N02)-C(-0)-N(CH3)-~ (-# = bond to AC) and Ac for a c~ oul~d corresponds to a group of Table I.2 20 Table 1085 Compounds of the general formula I.C In = 0) in which UR' is methoxy, VR" is ethoxy, yc is CH-C(N02)-C(=0)-N(CH3)-# (-# - bond to AC) and Ac for a co,.,~ou,~d corresponds to a group of Table I.2 Table 1086 Compounds of the general formula I.C (n = 0) in which UR' i8 ethoxy, VR" is ethoxy, yc is CH=C(N02)-C(=0)-N(CH3)-~ (-# - bond 30 to AC) and Ac for a c~ oul-d corresponds to a group of Table I.2 Table 1087 ~
Compounds of the general formula I.C (n - 0) in which UR' is 35 methylamino, VR" is methoxy, yc is. CH=C(N02)-C(sO)-N(CH3)-# (-# -bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1088 CG..,~o~nds of the general formula I.C (n - 0) in which UR' is ethyl.~mino, VR" is methoxy, yc is CH2C(N02)-C(=0)-N(CH3)-# (-# -bond to AC) and Ac for a compound corresponds to a group of Table I.2 ~5 -~ 295 219~'122 Table 1089 Compounds of the general formula I.C (n = 0) in which UR' is methylamino, ~R" i8 ethoxy, yc is CH=C(NO2)-C(=O)-N(CH3)-# (-# =
5 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1090 10 Compounds of the general formula I.C (n = 0) in which UR' is ethylamino, VR" i8 ethoxy, yc is CH=C(NO2)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 lS Table 1091 ( CG...~o~nds of the general formula I.C (n = 0) in which UR' is methoxy, VR" i8 methylamino, yc is CH=C(NO2)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a compound corresponds to a group of Table Z0 I.2 Table 1092 Compounds of the general formula I.C (n = 0) in which UR' is 25 ethoxy, VR" i8 methylamino, yc is CH=C(N02)-C(-O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1093 Co...~ounds of the general formula I.C (n = 0) in which UR' i8 methoxy, VR" i 8 ethyla~ino, yc is CH=C(N02)-C(=O)-N(CH3)-# (-~ =
bond to AC) and Ac for a c~...~ound corresponds to a group of Table I.2 Table 1094 Compounds of the general form~la I.C (n = 0) in ~hich UR' is ethoxy, VR" is ethylamino, yc is CH=C(NO2)-C('O)-N(CH3)-# (-# =
40 bond to AC) and Ac for a cG...~o~nd corresponds to a group of Table I.2 Table I.l 45 No. Ac No. Ac 4 CH(CH3)z CH2CH2CHzCH3 6 CH ( CH3 ) CH2CH3 7 CH2CH ( CH3 ) 2 B C(CH3)3 CHzcH=cH2 1 0 CH2CH=CHCH3 11 . CH2CH-CHCl 12 CH2C = CH
15 14 Cyclopropyl C l S Cyclopentyl 1 6 Cyclohexyl 18 C6Hs--CH2 ~, .
~ 2199~22 Table I.2 No. Ac CH(cH3)2 CH2CH2CH2cH3 10 6 CH(cH3)cH2cH3 7 CH2CH(CH3)2 8 . C(CH3)3 g Cyclopropyl Cyclopentyl 15 11 Cyclohexyl ' 12 C6H5 13 C6Hs-CH2 20 Table 1095 Compounds of the general formula I.D (n = 0) in which UR' is methoxy, VR" is methoxy and Ad for a ~v...~ound corresponds to a group of Table J
Table 1096 Compounds of the general formula I.D (n = 0) in which UR' is ethoxy, VRn is methoxy and Ad for a cv,~,~ound corresponds to a 30 group of Table J
Table 1097 Compounds of the general formula I.D (n = 0) in which UR' is 35 methoxy, VR" is ethoxy and Ad for a compound corresponds to a group of Table J
Table 1098 40 Compounds of the general formula I.D (n = 0) in which UR' is ethoxy, VR" is ethoxy and Ad for a compo~nd corresponds to a group of Table J
0050~45204 298 2 1 9 9il 2 2 Table 1099 Cv.,,pvunds of the general formula I.D (n - 0) in which UR' is methylamino, VR" is methoxy and Ad for a cG...~ound corresponds to a 5 group of Table J
Table 1100 Compounds of the general formula I.D (n ~ 0) in which UR' i8 10 ethylamino, VR~ i8 methoxy and Ad for a c~."po~nd corresponds to a group of Table J
Table 1101 15 Compounds of the general formula I.D (n = 0) in which UR' is ( methylamino, VR" is ethoxy and Ad for a cv.,,p~r~d corresponds to a group of Table J
Table 1102 Compounds of the general formula I.D (n = 0) in which UR' is ethylamino, VR" is ethoxy and Ad for a ~o~,o~.,d corrssponds to a group of Table J
25 Table 1103 Compounds of the general formula I.D (n = 0) in which UR' is methoxy, VR" i8 methylamino and Ad for a ~-v..~oul~d corresponds to a group of Table J
Table 1104 Co...pounds of the general formula I.D (n - 0) in which UR' is ethoxy, VRn is methylamino and Ad for a co..,~o~nd corresponds to a 35 group of Table J
Table 1105 ~
Co~ ounds of the general formula I.D (n e O) in which UR' is 40 methoxy, VRN is ethylamino and Ad for a compound corresponds to a group of Table J
~ ~ 00~/4$204 2199-~22 ~ 29 ~able 1105 Compoun~s o~ th~ ~eneral formula I ;~ (n - 0) in which UR~ is ethoxy, YR" is ~hyl~; n~ and Ad ~ a co~rolln~l cc~rrespon~ tD a 5 gxoup of Table J
Table ~
.. ... . .
Elo. Ae .. ....
10 1 Cyclopropyl , .. ..
~Y~ u~yi 3 Cyclopentyl 4 Cyclt3hexyl 1- ~ 4-OC2tls-C6E~4 ) -2, 2-~12-~y~lo~ropyl l-~H3--2, 2--C12--cyclo~u~
7 1--CF3--cyclopropy 1 8 l-C2H5--cyc loyl opy 1 9 1-~2~CEI3-cyclo~opyl 2C\ ~ 0 1--C~ CH 2--c:y~lv~
11 1- (CE~2-C6~ ~ -cy~lopr~p~l 12 1-{~ -(4--F-C6H4~ ]-~y~l~propyL
13 1--l CH~ ~ 3--F-~ H4 ~ ] -cy~ lopr 4p~ l ~S 14 1- t C~E~2- ~ 4-Cl-C~ -cyclopropyl lS l-t~-(3-Cl-C~H~? ]~cyc~ propyl 16 l-{~H~-[4-C~CH3)~C~ ,]}--~y~lo~ yl 17 1-CE~ cyclop~o~l 3~ 18 2--~H3 cycluy~ yl 1 g 2, 2 ~ --CyClGp ' vp~ 1 1-C~6EI5-~:YC~10~ yl 21 2--CGH5--cyclop~opyl ~ 1- ( 2-~1--C~H4 3--cy~lv~lo~?yl 3s 2 3 1--~ 3--~l--C~H4 )--cyclo~ r U~y 1 24 1- ( 4-Cl-C6~4 ~ -cyclopropyl ~5 1--( 7 ,. 4-C12--t~6H3 ) -cy~ pl4~
2 6 1--t ~, ~--Cl2--C~H3 )--cyclu~lu~ 1 2~ 6--~12--C6H3)~CYC 10PLo~
2~ 5, 4-C1Z-C~3 ~ -CY~ 1U~1 29 1~ ~ 2--F--C:6~1~, )--CYC:1OPrC~PY1 1~ --F--C6H4)~CYCLr-~PY4PYL
;~ 1 1- ( 4 -F-~I4 )--CYC 14~LUYY 1 3 2 1~ ( :~--Br-C~E~4 )--C:YC 1OP1 OP~ 1 ~ 3 1--~ 3 -: 3r-C6H~ y~l~pL o~l .
219~22 34 1-(4-Br-C6H4)-CYC1OPrOPY1 1-(2-CH3-C6H4)-CYC1OPrOPY1 36 1-(3-CH3-C6H4)-CYC1OPrOPY1 5 37 1-(4-CH3-C6H~)-CYC1OPrOPY1 38 1~[2~4_(CH3)2_C6H3]_CYC1OPrOPY1 39 1-t2~5-(CH3)2-C6H3]-CYC1O~LOP~1 1~t2~6~(CH3)2~C6H3]-CYC1OPrOPY1 41 1-t3~4-(CH3)2-C6H3]-CYC1OPrOPY1 1-~4-C(CH3)3-C6H4]-CYC1OPrOPY1 43 1-(3-CF3-C6H4)-CYC1OPrOPY1 44 1-(2-OCH3-C6H4)-CYC1OPrOPY1 1-(3-OCH3-C6H4)-CYC1OPrOPY1 15 46 1-(4-OCH3-C6H4)-CYC1OPLO~Y1 ( 47 1-12~4-(OCH3)2-C6H3]-CYC1~Pr~PY1 48 1-~2~S-(OCH3)Z-C6H3]-CYC1OPrOPY1 49 1~t2~6~(OCH3)2-C6H3]-CYC1OPrOPY1 20 50 1_t3~4_(0CH3)2-C6H3]-CYC1OPL~1 51 2,2-(CH3)2-CYC1OPrOPY1 52 2~2~(CH3)2~3~~CH=C(CH3)2]-CYC1OPrOPY1 53 2~2~(CH3)2~3~(CH=CC12)-CYC1OPrOPY1 2~2~(CH3)2-3-(CH=CBr2)-CYC1OPrOPY1 2~2~(CH3)2~3~(CH2CC1-CF3)-CYC1OPrOPY1 56 2~2-C12-3~3-(CH3)2-CYC1OPrOPY1 57 2~2~3~3-(CH3)4-CYC1OPrOPY1 58 2~2~(CH3)2~3~(CH=CF2)-CYC1OPrOPY1 30 59 2~2~(CH3)2~3~(CH3CF-CF3)-CYC1OPrOPY1 f~ 60 2~2~(CH3)2~3~~CH=C(CH3)-CO2CH3]-CYC10PrOPY1 61 2~2~(CH3)2~3~(CH=CHCH=CC12)-CYC1OPrOPY1 62 2,2-(CH3)2-3-(CHBrCBr3)-cyclopropyl 35 63 2~2-(CH3)Z-3- (cHBrccl2Br)-cyclopropyl 64 2,2-(CH3)2-3-(CYC1OPentY1idenemethY1)-CYC1OPrOPY1 2~2-(CH3)2-3-[4-C(CH3)3-C6H4]-CYC1OPrOPY1 40 Tab1e 1107 COmPOUndS Of the genera1 fOrmU1a I.E (n = 0) in WhiCh UR' ~S
methOXY~ VR" is methOXY~ ye is ~CH-NO~~ (~# = bOnd to Ae) and Ae fOr a COmPOUnd COrreSPOndS tO a grOUP Of Tab1e K.1 UV~/4~U4 ~ 301 2199'122 Table 1108 Compounds of the general formula I.E (n = 0) in which UR' is ethoxy, VR" is methoxy, ye is -CHzNO-# (~~ = bond to Ae) and Ae 5 for a c~ po~L.d corresponds to a group of Table K.1 Table 1109 Compounds of the general formula I.E (n = 0) in which UR' is 10 methoxy, VR" i8 ethoxy, ye is -CH2N0-~ = bond to Ae) and Ae for a compound corresponds to a group of Table K.l Table 1110 15 CoA,.~oullds of the general formula I.E (n = 0) in which UR' is C ethoxy, VR" is ethoxy, YQ is -CHsN0-# (-~ = bond to Ae) and Ae for a co,l,pound corresponds to a group of Table R.l Table 1111 Compounds of the general formula I.E (n = 0) in which UR' is methylamino, VR" is methoxy, ye is -CH5NO~ = bond to Ae) and Ae for a ~v..,~ol~nd corresponds to a group of Table K.l 25 Table 1112 Compounds of the general formula I.E (n 5 O) in which UR~ is ethylamino, VR is ~ethoxy, ye i8 -CH=NO-# (-~ = bond to Ae) and Ae for a co,.,~oul,d corresponds to a group of Table K.l f- Table 1113 ., Cc~ ou--ds of the general formula I.E (n = 0) in which UR~ is methylamino, VR" is ethoxy, ye is -CH=NO-~ z bond to Ae) and 35 Ae for a co.,.pound corresponds to a group of ~able K.l Table 1114 Compounds of the general formula I.E (n = 0) in which UR' is 40 ethylamino, VR" is ethoxy, ye is -CH=NO-~ = bond to A~) and Ae for a co...~nd corresponds to a group of Table K.l u~ls~ u~
~ 302 ~ 1 9 g ~ 2 2 Table 1115 Compounds of the general formula I.E (n = 0) in which UR' is methoxy, VR" is methylamino, ye is -CH=NO-# ( - ~ = bond to Ae) and 5 Ae for a compound corresponds to a group of Table K.l Table 1116 Compounds of the general formula I.E (n - 0) in which UR' is 10 ethoxy, VR" i~ methylamino, ye i8 -CH=N0-* (-# = bond to Ae) and Ae for a compound corresponds to a group of Table X.l Table 1117 15 Compounds of the general formula I.E (n ~ 0) in which UR' i8 methoxy, VR" is ethylamino, ye is -CH=No-$ (-# ~ bond to Ae) and ~ A' for a ~v.. ~o~nd corresponds to a group of Table K.l Table 1118 Compounds of the general formula I.E (n = o) in which UR' is ethoxy, VR" i8 ethylamino, ye is -CH=N0-# (-# = bond to Ae) and Ae for a cG,..~ou.ld corresponds to a group of Table K.l 25 Table 1119 Compounds of the general formula I.E (n = 0) in which UR' is methoxy, VR~ is methoxy, Y~ is -CH=N-NH-~ t-# = bond to Ae) and A~
for a compound corresponds to a group of Table K.2 - Table 1120 Compounds of the general formula I.E (n 2 O) in which UR' is ethoxy, VRn is methoxy, ye is -CHsN-NH-~ (-# = bond to Ae) and Ae 35 for a compound corresponds to a group of Table X.2 Table 1121 Compounds of the general formula I.E (n 5 0) in which UR' is 40 methoxy, VR" is ethoxy, ye is -CH=N-NH-~ = bond to Ae) and Ae for a compound corresponds to a group of Table K.2 0~50/4S2~4 219~422 Table 1122 Compounds of the general formula I.E (n = 0) in which UR' is ethoxy, VR" is ethoxy, ye iS -CH=N-NH-~ (-# = bond to Ae) and Ae 5 for a compound corresponds to a group of Table K.2 Table 1123 Compounds of the general formula I.E (n = 0) in which UR' is 10 methylamino, VR" is methoxy, ye is -CH=N-NH-~ 5 bond to Ae) and AQ for a cor..~ound corresponds to a group of Table K.2 Table 1124 15 c~ o~nds of the general formula I.E (n - 0) in which UR' is ' ethylamino, VR" is methoxy, ye iS -CH~N-NH-* (-# - bond to Ae) and Ae for a cv"~o~nd corresponds to a group of Table K.2 Table 1125 Compounds of the general formula I.E (n = 0) in which UR' is methylamino, VR" is ethoxy, ye is -CH=N-NH-# (-# = bond to Ae) and Ae for a c~,..~o~nd corresponds to a group of Table K.2 25 Table 1126 CGl.L~vunds of the general formula I.E (n = 0) in which UR' is ethylamino, VR" is ethoxy, ye i8 -CH=N-NH-~ = bond to Ae) and Ae for a compound corresponds to a gxoup of Table K.2 ~- Table 1127 Cc~ ullds of the general formula I.E (n = 0) in which UR' is methoxy, VR" is methylamino, ye i8 -CH=N-NH-# (-# = bond to Ae) 35 and Ae for a compound corresponds to a group of Table K.2 Table 1128 r~- lunds of the general formula I.E (n = 0) in which UR' i8 40 ethoxy, VR~ is methylamino, ye iS -CH=N-NH-~ = bond to Ae) and A~ for a compound corresponds to a group of Table K.2 2199~22 Table 1129 CGu~ou,lds of the general formula I.E (n = 0) in which UR~ is methoxy, VR" i~ ethylamino, ye is -CH=N-NH-# (-# = bond to Ae) and 5 Ae for a compound corresponds to a group of Table K.2 Table 1130 Compounds of the general formula I.E (n = 0) in which UR' is 10 ethoxy, VR" is ethylamino, ye is -CH=N-NH~ = bond to AQ) and Ae for a compound corresponds to a group of Table K
Table K.l 15 Compound No. R2 t 1.467 H
1.468 CH3 1.469 CH3CH2 1.470 CH3CH2CH2 1.471 CH2ZcH-cH2 1.472 CH3-CH=CH
1.473 CH3-CH=CH-CH(CH3) 1.474 FH3 HC_C l = CH C
1.475 HC_C-CH2 1.476 CH3-O-CH2-CH2 1.477 C2Hs-o-cH2-cH2 30 1.478 Cl-CH2-CH2 1.479 Cyclo-c3Hs-cH2 1.480 CH3-cH=cH-cH2 1.481 CH2=cH-cH2-cH2 35 1.482 CH3C_C-cH2 1.483 CH3CH2-C-C-cH2 1.484 CH3-(CH2)3 1.485 CH3-(CH2)4 40 1.486 (CH3)3C
1.487 Cyclo-C6Hll 1.488 2-CH3-Cyclo-CcH1o 1.489 C6Hs-CH2 4 1.490 2-F-C6H4-CH2 1.491 3-F-C6H4-CH2 1.492 4-F-C6H4-CH2 0050/45204 2 ~ 9 9 i 2 2 COI..~O~nd NO. R2 1.493 2-cl-c6H4-cH2 1.494 3-cl-C6H4-CH2 5 1.495 4-Cl-C6H4-CH2 1.496 2,3-cl2-c6H3-cH2 1.497 2,4-cl2-C6H3-cH2 1.498 2,5-Cl2-C6H3-CH2 1.499 2,6-cl2-C6H3-cH2 1.500 3,4-cl2-c6H3-cH2 1.501 2-CH3-c6H4-cH2 1.502 3-CH3-C6H4-CH2 1.503 4-cH3-c6H4-cH2 15 1.504 2,3-(CH3)2-C6H3-CH2 (1.505 2,4-(CH3)2-C6H3-CH2 1.506 2,5-(CH3)2-C6H3-CH2 1.507 3,4-(CH3)2-C6H3-CH2 20 1.508 3,5-(CH3)2-C6H3-CH2 1.509 4~5-(CH3)2-C6H3-CH2 1.510 2,3,4-(CH3)3-C6H2-CH2 1.511 2,4,5-~CH3)3-C6H2-CH2 25 1.512 2,4,6-(CH3)3-C6H2-CH2 1.513 2,3,6-(CH3)3-C6H2-CH2 1.514 2-CF3-C6H4-CH2 1.515 3-CF3 C6H4-CH2 1.516 4-CF3-C6H4-CH2 30 1.517 2-CH3-3-CF3-C6H3-CH2 1.518 2-CH3-4-CF3-C6H3-CH2 1.519 2-CF3-3-CH3-C6H3-CH2 1.520 2-CF3-4-CH3-C6H3-CHz 35 1.521 2-CF3-5-CH3- 4 H3-CH2 1.522 2--CH3--5--CF3--C6H3--CH2 1.523 2-Br-C6H4-CH2 1.524 3-Br-C6H4-CH2 40 1.525 4-Br-C6H4-CH2 1.526 2-(iso-Propyl)-C6H4-CH2 1.527 3-(iso-propyl)-c6H4-cH2 1.528 4-(iso-Propyl)-C6H4-CH2 1.529 2-(iso-Propyl)-3-Cl-C6H3-CH2 1.530 2-(iso-Propyl)-4-Cl-C6H3-CH2 1.531 2-(iso-Propyl)-5-Cl-C6H3-CH2 0050/45204 2 1 9 9 4 ~ 2 Compound No. R2 1.532 2-cH3-3-(iso-propyl)-c6H3-cH2 1.533 2-CH3-4-(iso-Propyl)-C6H3-CH2 5 1.534 2-CH3-5-(iso-Propyl)-C6H3-CH2 1.535 2-t-C4Hg-C6H4-CH2 1.536 3-t-C4H9-C6H4-CH2 1.537 4-t-C4Hg-C6H4-CH2 1.538 2-CH3-3-t-C4H9-C6H3-CHz 1.539 2-CH3-4-t~C4Hs~C6H3~CH2 1.540 2-CH3-5-t-C4Hg-C6H3-CH2 1.541 3-CH3-4-t-C4Hg-C6H3-CH2 1.542 3-CH3-5-t-C4Hg-C6H3-CH2 15 1.543 2-cl-3-t-c4H9-c6H3-cH2 1.544 2-cl-4-t-c4H9-c6H3-cH2 1.545 2-cl-5-t-c4H9-c6H3-cH2 1.546 3-Cl-4-t-C4Hs~C6H3~CH2 20 1.547 3-Cl-5-t-C4Hg-C6H3-CH2 1.548 2-OCH3-C6H4-CH2 1.549 3-OCH3-C6H4-CH2 1.550 4-OCH3-c6H4-cH2 25 1.551 2-CH3-3-0CH3-C6H3-CH2 1.552 2-CH3-5-0CH3-C6H3-CH2 1.553 3-CH3-4-0CH3-C6H3-cH2 1.554 3-CH3-5-0CH3-C6H3-cH2 1.555 2-Cl-3-0CH3-C6H3-CH2 30 1.556 2-Cl-4-0CH3-C6H3-CH2 1.557 2-C1-5-OCH3-C6H3-CH2 1.558 2-ocH3-3-cl-c6H3-cH2 1.559 2-ocH3-4-cl-c6H3-cH2 35 1.560 2-OCH3-5-Cl-C6H3-CH2 1.561 2-CH3-4-(Cyclohexyl)-C6H3-CH2 1.562 2-CH3-4-C6H5-C6H3-CH2 1.563 2-CH3-3-Br-C6H3-CH2 40 1.564 2-CH3-4-Br-C6H3-CH2 1.565 2-CH3-5-Br-C6H3-CH2 1.566 2-CH3-3-(methoxyiminoethyl)-C6C3-CH2 1.567 2-methoxyiminoethyl-C6H4-CH4 1.568 3-methoxyiminoethyl-C6H4-CH4 1.569 2-CH3-4-(methoxyiminoethyl)-C6H3-CH2 1.570 2-Phenyl-C6H4-CH2 0050/45204 2 1 9 ~ ~ 2 2 Col,.pound No. RZ
1.571 3-Phenyl-C6H4-CH2 1.572 4-Phenyl-C6H4~CH2 5 1.573 2-Phenoxy-C6H4~CH2 1.574 3-PhenoXy-c6H4-cH2 1.575 4-Phenoxy-c6H4-cH2 1.576 2-Benzyloxy-C6H4-CH2 1.577 3-BenzyloXy-c6H4-cH2 1.578 4-Benzyloxy-c6H4-cH2 1.579 l-Naphthyl-CH2 1.580 2-Naphthyl-CH2 1.581 9-Anthryl-CH2 15 1.582 2-CH3-3-C6HsO~C6H3~CH2 1.583 2-CH3-4-C6H50-C6H3-CH2 1.584 2-CH3-5-C6HsO-C6H3-CH2 1.585 3-CH3-4-C6H50-C6H3-CH2 20 1.586 4-CH3-5-C6HsO~C6H3~CH2 1.587 2-Cl-3-C6H50-C6H3-CH2 1.588 2-Cl-4-C6H50-C6H3-CH2 1.589 2-Cl-5-C6H50-C6H3-CH2 25 1.590 3-Cl-4-C6H50-C6H3-CH2 1.591 3-Cl-5-C6H50-C6H3-CH2 1.592 2-CH3-4-C02CH3-C6H3-CH2 1.593 2-CH3-5-C02CH3-C6H3-CH2 1.594 C6H5-CH(CH3) 30 1.595 2-F-C6H4-CH(CH3) .1.596 2-F-C6H4-CH(CH3) 1.597 4-F-C6H4-CH(CH3) 1.598 2-C1-C6H4-CH~CH3) 35 1.599 3-Cl-C6H4-CHtCH3) 1.600 4-C1-C6H4-CH(CH3) 1.601 2,3-Cl2-C6H3-CH(CH3) 1.602 2,4-Cl2-C6H3-CH(CH3) 40 1.603 2,5-Cl2-C6H3-CH(CH3) 1.604 2,6-C12-C6H3-CH(CH3) 1.605 3,4-Cl2-C6H3-CH(CH3) 1.606 2-CH3-C6H4-CH(CH3) 1.607 3-CH3-C6H4-CH(CH3) 1.608 4-CH3-C6H4-CH(CH3) 1.609 2,3-(CH3)2-C6H3-CH(CH3) -0050~45204 ~ 2199 122 Compound No. R2 1.610 2,4-(CH3)2-C6H3-CH(CH3) 1.611 2,5-(CH3)2-C6H3-CH(CH3) 5 1.612 3,4-(CH3)2-C6H3-CH(CH3) 1.613 3,5-(CH3)2-C6H3-CH(CH3) 1.614 4~5-(cH3)2-c6H3-cH(cH3) 1.615 2,3,4-(CH3)3-C6H2-CH(CH3) 1.616 2,4,5-(CH3)3-C6H2-CH(CH3) 1.617 2,4,6-(CH3)3-C6Hz-CH(CH3) 1.618 2,2,6-(CH3)3-C6H2-CH(CH3) 1.619 2-CF3-C6H4-CH(CH3) 1.620 2-CF3-C6H4-CH(CH3) 15 1.621 4-CF3-C6H4-CH(CH3) 1.622 2-CH3-3-CF3-C6H3-CH(CH3) 1.623 2-CH3-4-CF3-C6H3-CH(CH3) 1.624 2-CF3-3-CH3-C6H3-CH(CH3) 20 1.625 2-CF3-4-CH3-C6H3-CH(CH3) 1.626 2-CF3-5-CH3-C6H3-CH(CH3) 1.627 2-CH3-5-CF3-C6H3-CH(CH3) 1.628 2-Br-C6H4-CH(CH3) 25 1.62g 3-Br-C6H4-CH(CH3) 1.630 4-Br-C6H4-CH(CH3) 1.631 2-(iso-Propyl)-C6H4-CH(CH3) 1.632 3-(iso-Propyl)-C6H4-CH(CH3) 1.633 4-(iso-Propyl)-C6H4-CH(CH3) 30 1.634 2-(iso-Propyl)-3-Cl-C6H3-CH(CH3) 1.635 2-(iso-Propyl)-4-Cl-C6H3-CH(CH3) 1.636 2-(iso-Propyl)-5-Cl-C6H3-CH(CH3) 1.637 2-CH3-3-(iso-Propyl)-C6H3-CH(CH3) 35 1.638 2-CH3-4-(iso-Propyl)-C6H3-CH(CH3) 1.639 2-CH3-5-(iso-Propyl)-C6H3-CH(CH3) 1.640 2-t-C4Hg-C6H4-CH-(CH3) 1.641 3-t-C4Hg-C6H4-CH~(CH3) 40 1-642 4-t-C4Hs~C6H4~CH(cH3) 1.643 2-CH3-3-t-C4Hg-C6H3-CH(cH3) 1.644 2-CH3-4-t-C4Hg-C6H3-CH(cH3) 1.645 2-CH3-5-t-C4Hg-C6H3-CH(CH3) 1.646 3-CH3-4-t-C4Hg-C6H3-CH(CH3) 1.647 3-CH3-5-t-C4Hg-C6H3-CH(CH3) 1.648 2-Cl-3-t-C4Hg-C6H3-CH(CH3) .
~199422 Compound No. R2 1.649 2-Cl-4-t-C4Hg-C6H3-CH(CH3) 1.650 3-Cl-4-t-C4Hg-C6H3-CH(CH3) 5 1.651 3-Cl-5-t-C4Hg-C6H3-CH(CH3) 1.652 2-OCH3-C6H4-CH2-CH(CH3) 1.653 3-OCH3-C6H4-CH2-CH(CH3) 1.654 4-OCH3-C6H4-CH2-CH(CH3) 1.655 2-CH3-3-OCH3-C6H3-CH(CH3) 1.656 2-CH3-4-OCH3-C6H3-CH(CH3) 1.657 2--CH3--5--OCH3--C6H3--CH(CH3) 1.658 3-CH3-5-OCH3-C6H3-CH(CH3) 1.659 3-CH3-5-OCH3-C6H3-CH(CH3) lS 1.660 2-Cl-3-OCH3-C6H3-CH(CH3) .1.661 2-Cl-4-OCH3-C6H3-CH(CH3) 1.662 2-Cl-5-OCH3-C6H3-CH(CH3) 1.663 2-0CH3-3-Cl-C6H3-CH(CH3) 20 1.664 2-OCH3-4-Cl-C6H3-CH(CH3) 1.665 2-OCH3-5-Cl-C6H3-CH(CH3) 1.666 2-CH3-4-(Cyclohexyl)-C6H3-CH(CH3) 1.667 2-CH3-4-C6H5-C6H3-CH(CH3) 25 1.668 2-CH3-3-Br-C6H3-CH(CH3) 1.669 2-CH3-4-Br-C6H3-CH(CH3) 1.670 3-CH3-5-Br-C6H3-CH(CH3) 1.671 2~CH3-3-(methoxyiminoethyl)-C6H3-CH(CH3) 1.672 2-methoxyiminoethyl-C6H4-CH(CH3) 30 1.673 3-methoxyiminoethyl-C6H4-CH(CH3) 1.674 2-CH3-4-(methoxyiminoethyl)-C6H3-CH(CH3) 1.675 2-Phenyl-C6H4-CH(CH3) 1.676 3-Phenyl-C6H4-CH(CH3) 35 1.677 4-Phenyl-C6H4-CH(CH3) 1.678 2-Phenoxy-C6H4-CH(CH3) 1.679 3-Phenoxy-C6H4-CH(CH3) 1.680 4-Phenoxy-C6H4-CH(CH3) 40 1.681 2-Benzyloxy-C6H4-CH(CH3) 1.682 3-Benzyloxy-C6H4-CH(CH3) 1.683 4-Benzyloxy-C6H4-CH(CH3) 1.684 1-Naphthyl-CH(CH3) 1.685 2-Naphthyl-CH(CH3) 1.686 9-Anthryl-CH(CH3) 1.687 2-CH3-3-C6H50-C6H3-CH(CH3) .
Compound No. R2 1.688 2-CH3-4-C6H50-C6H3-CHtCH3) 1.689 2-CH3-5-C6H50-C6H3-CH(CH3 5 1.690 3-CH3-4-C6HsO-C6H3-CH(CH3) 1.691 4-CH3-5-C6H50-C6H3-CH(CH3) 1.692 2-Cl-3-C6H50-C6H3-CH(CH3) 1.693 2-Cl-4-C6H50-C6H3-CH(CH3) 1.694 2-Cl-5-C6H50-C6H3-CH(CH3) 1.695 3-Cl-4-C6H50-C6H3-CH(CH3) 1.696 3--Cl--5--C6H50--C6H3--CH(CH3) 1.697 2-CH3-4-C02CH3-C6H3-CH(CH3) 1.698 2-CH3-5-C02CH3-C6H3-CH(CH3) 15 1.699 C6H5-(cH2)2 (1.700 2-F-C6H4-(CHz)2 1.701 2-F-C6H4-(CH2)2 1.702 4-F-C6H4-(CH2)2 20 1.703 2-Cl-C6H4-(CH2)2 1.704 3-Cl-C6H4-(CH2)2 1.705 4-Cl-C6H4-(CH2)2 1.706 2,3-Cl2-C6H3-(CH2)2 25 1.707 2,4-cl2-c6H3-(cH2)2 1.708 2,5-cl2-C6H3-(cH2)2 1.709 2,6-Cl2-C6H3-(CH2)2 1.710 3,4-Cl2-C6H3-(CH2)2 1.711 2-CH3-C6H4-(CH2)2 30 1.712 3-CH3-C6H4-(CH2)2 1.713 4-CH3-C6H4-(CH2)2 1.714 2,3-(CH3)2-C6H3-(CH2)2 1.715 2,4-(CH3)2-C6H3-(CH2)2 35 1.716 2~5-(CH3)z-C6H3-(CH2)2 1.717 3,4-(CH3)2-C6H3-(CH2)2 1.718 3,5-(CH3)2-C6H3-(CH2)2 1.719 4,5-(CH3)2-C6H3-(CH2)2 40 1.720 2,3,4-(CH3)3-C6H2-(CH2)2 1.721 2,4,5-(CH3)3-C6H2-(CH2)2 1.722 2,4,6-(CH3)3-C6H2-(CH2)2 1.723 2,2,6-(CH3)3-C6H2-(CH2)2 1.724 2-CF3-C6H4-(CH2)2 1.725 2-CF3-C6H4-(CH2)2 1.726 4-CF3-C6H4-(CH2)2 2t 99422 Compound No. R2 1.727 2-CH3-3-CF3-C6H3-(cHz)2 1.728 2-CH3-4-CF3-C6H3-(CH2) 1.729 2-CF3-3-CH3-C6H3-(CH2)2 1.730 2--CF3--4--CH3--C6H3--(CH2)2 1.731 2-CF3-5-CH3-C6H3-(CH2)2 1.732 . 2-CH3-5-CH3-C6H3-(CH2)2 1.733 2-Br-C6H4-(CH2)2 1.734 3-Br-C6H4-(CH2) 2 1.735 4-Br-C6H4-(CH2)2 1.736 2-(iso-Propyl)-C6H4-(CH2)2 1.737 3--(iso--Propyl)-C6H4--(CH2) 2 1.738 4--(iso--Propyl )--C6H4--(CH2) 2 ( 1.739 2--(iso--Propyl)--3--Cl--C6H3--(CH2) 2 1.740 2-(iso-Propyl)-4-Cl-C6H3-(CH2)2 1.741 2--(iso--Propyl)-- 5--Cl--C6H3--(CH2)2 1.742 2--CH3--3--(iso--Propyl)-C6H3--(CH2)2 1.7 43 2--CH3--4--(iso-Propyl)-C6H3-(CH2) 2 1.7 44 2--CH3--5--(iso-Propyl)-C6H3-(CH2)2 1.7 45 2--t--C4Hg-C6H4--(CH2)2 1.74 6 3--t--C4Hg-C6H4--(CH2)2 1.747 4-t-C4Hg-C6H4-(CH2)2 1.7 48 2--CH3--3--t--C4Hg--C6H3-(CH2)2 1.749 2-CH3-4-t-c4Hg-c6H3-(cH2)2 1.750 2-CH3-5-t-C4Hg-C6H3-(cH2)2 1.7 51 3--CH3--4--t--C4Hg--C6H3--(CH2)2 1.7 52 3--CH3--5--t--C4Hg--C6H3--(CH2)2 1.7 53 2--Cl--3--t--C4Hg--C6H3--(CH2)2 1.754 2-Cl-4-t-C4Hg-C6H3-(CH2)2 1.755 2-cl-5-t-c4H9-c6H3-(cH2)2 1.75 6 3--Cl--4--t--C4Hg--C6H3--(CH2)2 1.7 57 3--Cl--5--t-C4Hg--C6H3--(CH2)2 1.758 2-OCH3-C6H4-(CH2)2 40 1.759 3-OCH3-C6H4-(CH2)2 1.760 4-OCH3-C6H4-(CH2)2 1.761 2-CH3-3-OCH3-C6H3-(CH2)2 1.762 2-CH3-4-OCH3-C6H3-(CH2)2 1.763 2-CH3-5-OCH3-C6H3-(cH2)2 1.764 3-CH3-4-OCH3-C6H3-(CH2)2 1.765 3-CH3-5-OCH3-C6H3-(CH2)2 0050/45204 2 1 9 9 ~ 2 2 .
C~.llpound No. R2 1.766 2-Cl-3-OCH3-C6H3-(CH3) 2 1.767 2-Cl-4-OCH3-C6H3-(CH3) 2 5 1.768 2-Cl-5-OCH3-C6H3-(CH3)2 1.769 2-ocH3-3-cl-c6H3-(cH3) 2 1.770 2-ocH3-4-cl-c6H3-(cH3)2 1.771 2-ocH3-5-cl-c6H3-(cH3)2 1.772 2-CH3-4-(Cyclohexyl)-C6H3-(CH2)2 1.773 2-CH3-4-C6Hs~C6H3~(CH2) 2 1.774 2-CH3-3-Br-C6H3-(CH2) 2 1.775 2-CH3-4-Br-C6H3-(CH2)2 1.776 3-cH3-5-Br-c6H3-(cH2)2 15 1.777 2-CH3-3-~methoxyiminoethYl)-C6H3-(CH2)2 ;~1.778 2-methoxyiminoethyl~C6H4~(CH2)2 1.779 3--methoxyiminoethyl-C6H4~(CH2)2 1.780 2-CH3-4-(methoxyiminoethyl)-C6H3~(CH2)2 20 1.781 2-Phenyl-C6H4-(CH2)2 1.782 3-Phenyl-c6H4-(cH2)2 1.783 4-Phenyl-c6H4-(cH2)2 1.784 2-Phenoxy-C6H4-(CH2)2 25 1.785 3-Phenoxy-C6H4-(cH2)2 1.786 4-Phenoxy-C6H4~(CH2)2 1.787 2-Benzyloxy-C6H4-(CH2) 2 1.788 2-BenzyloXy-c6H4-(cH2)2 1.789 4-Benzyloxy-C6H4-(cH2) 2 30 1.790 l-Naphthyl-(CH2)2 1.791 2-Naphthyl-(CH2) 2 1.792 9-Anthryl-tCH2)2 1.793 2-CH3-3-C6HsO-C6H3-(CH2) 2 35 1.794 2-CH3-4-C6H5O-C6H3-(CH2)2 1.795 2-CH3-5-C6H50-C6H3-(CH2)2 1.796 3-cH3-4-c6Hso-c6H3-(cH2)2 1.797 4 CH3-5-C6HsO-C6H3-(cH2)2 40 1.798 2-Cl-3-C6HsO-C6H3-(CH2)2 1.799 2-~1-4-C6HSO-C6H3-(CH2)2 1.800 2-Cl-5-C6HsO~C6H3~(CH2)2 1.801 3-Cl-4-C6HSO-C6H3-(CH2)2 1.802 3-Cl-5-C6HsO-C6H3-(CH2)2 1.803 2-CH3-4-C02CH3-C6H3-(CH2)2 1.804 2-CH3-5-C02CH3-C6H3-(CH2)2 0050/45204 ~ ~ 9 9 ~ 2 2 Compound No. R2 1.805 C6H5-cH=cH-cH2 1.806 2-F-c6H4-cH=cH-cH2 5 1.807 3-F-C6H4-CH=CH-CH2 1.808 4-F-C6H4-CH=CH-CH2 1.809 2-Cl-C6H4-CH=CH-CH2 1.810 3-Cl-C6H4-CH=CH-CH2 1.811 4-Cl-C6H4-CH=CH-CH2 1.812 2,3-cl2-c6H3-cH=cH-cH2 1.813 2,4-cl2-c6H3-cH=cH-cH2 1.814 2,5-Cl2-C6H3-CH=CH-CH2 1.815 2,6-Cl2-C6H3-CH=CH-CH2 15 1.816 3,4-Cl2-C6H3-CH=CH-CH2 (1.817 2-CH3-C6H4-CH=CH-CH2 1.818 3-cH3-c6H4-cH2cH-cH2 1.819 4-cH3-c6H4-cH=cH-cH2 20 1.820 2,3-(CH3)2-C6H3-CH=CH-CH2 1.821 2~4-(cH3)2-c6H3-cH=cH-cH2 1.822 2,5-(CH3)2-C6H3-CH=CH-CH2 1.823 3,4-~CH3)2-C6H3-CH=CH-cH2 25 1.824 3,5-(CH3)2-C6H3-CH=CH-CH2 1.825 4,5-(CH3)2-C6H3-CH=CH-CH2 1.826 2,3,4-(CH3)3-C6H2-CH=CH-CH
1.827 2,4,5-(CH3)3-C6H2-CH=CH-CH
1.828 2,4,6-(CH3)3-C6Hz-CH=CH-CH
30 1.829 2,3,6-(CH3)3-C6H2-CH=CH-CH
1.830 2-CF3-C6H4-CH=CH-CH2 1.831 3-cF3-c6H4-cH=cH-cH2 1.832 4-CF3-C6H4-CH=CH-cH2 35 1.833 2-CH3-3-CF3-C6H3-CH=CH-CH2 1.834 2-CH3-4-CF3-C6H3-CH=CH-CH2 1.835 2-CF3-3-CH3-C6H3-CH=CH-CH2 1.836 2--CF3--4--CH3--C6H3--CH=CH--CH2 40 1.837 2-CF3-5-CH3-C6H3-CH3CH-CH2 1.838 2-CH3-5-CF3-C6H3-CH=CH-CH2 1.839 C6Hs-(cH2)3 1.840 C6Hs-(CH2)4 1.841 C6H5-cH2cH=cH-cH2 1.842 4-F-C6H4-CH=CH-(CH2)2 1.843 CH30--CO--CH2 .
Compound No. R2 1.844 CH3CH20-cO-cH2 1.845 CH3-CO-CH2-CH2 5 1.846 t-C4HgO~CO~(CH2)3 1.847 t-C4HgO~CO-(CH2) 2 1.848 t-C4HgO~CO-cH2 1.849 n-C4H9O-CO-CH2 1.850 iso-C4HgO-C0~CH2 1.851 n-C3H7O-CO-CH2 1.852 ~ec.-C4HgO-CO~CH2 1.853 C6H5-CO-CH2 1.854 2-CH3-C6H4O-C0-CH2 15 1.855 3-CH3-C6H4O-cO-cH2 1.856 4-CH3-C6H4O-co-cH2 1.857 2-Cl-C6H4O-cO-cH2 1.858 3-Cl-C6H4O-cO-cH2 20 1.859 4-Cl-C6H4O-cO-cH2 1.860 C6H5-C(CH3)=CH-cH2 1.861 CH2-[pyrid-2-yl]
1.862 CH2-t3-Cl-pyrid-2-yl]
25 1.863 CH2-t4-Cl-pyrid-2-yl]
1.864 CH2-t3-CH3-pyrid-2-yl]
1.86S CH2-t4-CH3-pyrid-2-yl]
1.866 CH2-t3-CF3-pyrid-2-yl~
1.867 CH2-t4-CF3-pyrid-2-yl]
30 1.868 CH2-t3-Br-pyrid-2-yl]
1.869 CH2-[4-Br-pyrid-2-yl]
1.870 CH2-t3-F-pyrid-2-yl]
1.871 CH2-t4-F-pyrid-2-yl]
35 1.872 CH2-tpyrid-3-yl]
1.873 CH2-[2-Cl-pyrid-3-yl]
1.874 CH2-[pyrazin-2-yl]
1.875 CH2-tbenzopyrazin-2-yl]
40 1.876 CH2-[pyridazin-3-yl]
1.877 CH2-t3-CH3, 4-Cl-pyrid-2-yl]
1.878 CH2-t4-CH3, 3-Cl-pyrid-2-yl]
1.879 CH2-t4-CH3, 3-Br-pyrid-2-yl]
1.880 CH2-t6-CH3, 3-Cl-pyrid-2-yl]
1.881 CH2-t6-CH3, 3-Br-pyrid-2-yl]
1.882 CH2-t6-CH3, 3-CH3-pyrid-2-yl]
2~994~2 Cu~ o~ld No. R2 1.883 CH2-t4,6-(CH3)2-pyrid-2-yl]
1.884 CH2-[4-CF3, 3-Cl-pyrid-2-yl]
5 1.885 CH2-t3,6-Cl2-pyrid-2-yl]
1.886 CH2-~3,4-Cl2-pyrid-2-yl]
1.887 CH2-[5-Cl, 6-CH3-pyrid-2-yl]
1.888 CH2-[3-Cl, 4-OCH3-pyrid-2-yl]
1.889 CH2-~3-F, 6-Cl-pyrid-2-yl]
1.890 CH2-[4-Br, 6-NO2-pyrid-2-yl]
1.891 CH2-tfuran-2-yl]
1.892 CH2-[furan-3-yl]
1.893 CH2-~4-Cl-furan-2-yl]
15 1.894 CH2-[pyrrol-2-yl~
1.895 CH2-[pyrrol-3-yl]
1.896 CH2-[l-CH3-pyrrol-2-yl]
1.897 CH2-[l-CH3-pyrrol-3-yl]
20 1.898 CH2-[4,5-benzofuran-2-yl]
1.899 CH2-~4,5-benzothien-2-yl]
1.900 CH2-[pyrazol-5-yl]
1.901 CH2--tisoxazol--5--yl]
25 1.902 CH2-~4-Cl-isoxazol-5-yl]
1.903 CH2-[3-Cl-isoxazol-5-yl]
1.904 CH2-[4-CH3-isoxazol-5-yl]
1.905 CH2-[3-CH3-isoxazol-5-yl]
1.906 CHz-[3-CH3, 4-Cl-isoxazol-5-yl]
30 1.907 CH2-[4-CH3, 3-Cl-isoxazol-5-yl]
1.908 CH2-[thien-2-yl]
1.909 CH2-[thien-3-yl]
1.910 CH2-t3-Cl-thien-2-yl]
35 1.911 CH2-[4-Cl-thien-2-yl]
1.912 CH2-[5-Cl-thien-2-yl]
l.9I3 CH2-tindol-2-yl]
1.914 CH2-[isothiazol-5-yl]
40 1.915 CH2-[4-Cl-isothiazol-5-yl]
1.916 CH2-[3-Cl-isothiazol-5-yl]
1.917 CH2-[2-C6H5-oxazol-4-yl]
1.918 CH2-{2-[2-CH3-C6H4]-oxazol-4-yl}
1.919 CH2-{2-[3-CH3-C6H4]-oxazol-4-yl}
1.920 CH2-{2-[4-CH3-C6H4]-oxazol-4-yl}
1.921 CH2-~2-[2-F-C6H4]-oxazol-4-yl}
0050/45204 2 ~ 9 9 ~ 2 2 Compound No. R2 1.922 CH2-{2-t4-F-C6H4]-oxazol-4-yl}
1.923 CH2-{2-~2-CH3, 4-F-C6H3]-oxazol-4-yl}
5 1.924 CH2-{2-[2-CH3, 4-Cl-C6H3]-oxazol-4-yl}
1.925 CH2-{2-t5-CH3, 2-Cl-C6H3]-oxazol-4-yl}
1.926 CH2-{2-t2-CH3, 4-CH(CH3)2-C6H3]-oxazol-4-yl}
1.927 CH2-{2-~2,4-(CH3)2-C6H3]-oxazol-4-yl}
1.928 CH2-{2-t2,5-(CH3)2-C6H3]-oxazol-4-yl}
1.929 CH2-C--N
1.930 CH2CH=CHCH2-OC(CH3)3 1.931 CH2CH=C(CH3)CH2CH2CH=C(CH3)2 1.932 CH2cHec(cH3)cH2cH2cH=cHcH(cH3) 2 ,., 0050/4s204 2 1 9 9 ~ ~ 2 Table K.2 CG.I.~G1111d NO. R2 5 1.671 R2 1.672 Methyl 1.673 Ethyl 1.674 n-Propyl 1.675 iso-Propyl 1.676 n-Butyl 1.677 i~o-Butyl 1.678 sec-Butyl 1.679 tert-Butyl 15 1.680 n-Hexyl (.1.681 n-Decyl 1.682 Cyclopropyl 1.683 Cyclohexyl 20 1.684 l-Methylcyclopropyl 1.685 l-Methylcyclohexyl 1.686 Ethenyl 1.687 l-Propenyl 25 1.688 2-Methyl-l-propenyl 1.689 2-Propenyl 1.690 2-Butenyl 1.691 Phenyl 1.692 3-Fluorophenyl 1.693 4-Fluorophenyl 1.694 2-Chlorophenyl 1.695 3-Chlorophenyl 1.696 4-Chlorophenyl 35 1.697 Pentachlorophenyl 1.698 2,3-Dichlorophenyl 1.699 2,4-Dichlorophenyl 1.700 2,5-Dichlorophenyl 40 1.701 2,6-Dichlorophenyl 1.702 3,4-Dichlorophenyl 1.703 3,5-Dichlorophenyl 1.704 2,3,4-Trichlorophenyl 1.705 2,3,5-Trichlorophenyl 1.706 2,3,6-Trichlorophenyl 1.707 2,4,5-Trichlorophenyl .
0050/452~4 Compound No. R2 1.708 2,4,6-Trichlorophenyl 1.70g 3,4,5-Trichlorophenyl 5 1.710 2,3~4~5-Tetrachlorophenyl 1.711 2,3,4,6-Tetrachlorophenyl 1.712 2-Bromophenyl 1.713 3-Bromophenyl 1.714 4-Bromophenyl 1.715 2,4-Dibromophenyl 1.716 3-Br~ ~ g fluorophenyl 1.717 3-Bromo-4-methoxyphenyl 1.718 2-iodophenyl 15 1.719 3-iodophenyl 1.720 4-iodophenyl 1.721 2-Chloro-4-fluorophenyl 1.722 2-Chloro-5-fluorophenyl 20 1.723 2-Chloro-6-fluorophenyl 1.724 2-Chloro-4-bromophenyl 1.725 2-BL~- - g chlorophenyl 1.726 2-Br~~ q fluorophenyl 25 1.727 3-BL~_ q-chlorophenyl 1.728 3-Chloro-4-fluorophenyl 1.72g 3-Fluoro-4-chlorophenyl 1.730 2-Cyanophenyl 1.731 3-Cyanophenyl 30 1.732 4-Cyanophenyl f 1.733 2-Nitrophenyl 1.734 3-Nitrophenyl 1.735 4-Nitrophenyl 35 1.736 2-Methylphenyl 1.737 3-Methylphenyl 1.738 4-Methylphenyl 1.739 2,4-Dimethylphenyl 40 1.740 2,5-Dimethylphenyl 1.741 2,6-Dimethylphenyl 1.742 3,4-Dimethylphenyl 1.743 3,5-Dimethylphenyl 1.744 2,3,4-Trimethylphenyl 1.745 2,3,5-Trimethylphenyl 1.746 2,3,6-Trimethylphenyl Compound No. R2 1.747 2,4,5-Trimethylphenyl 1.748 2,4,6-Trimethylphenyl 5 1.749 3,4,5-Trimethylphenyl 1.750 Pentamethylphenyl 1.751 2-Methyl-5-methoxyphenyl 1.752 2-Methyl-6-methoxyphenyl 1.753 2-Methyl-4-iso-propoxyphenyl 1.754 2-Methyl-2,5-dimethoxyphenyl 1.755 2-Methoxyphenyl 1.756 3-Methoxyphenyl 1.757 4-Methoxyphenyl lS 1.758 2,3-Dimethoxyphenyl C 1.759 2~4-Dimethoxyphenyl 1.760 2,5-Dimethoxyphenyl 1.761 2,6-Dimethoxyphenyl 20 1~762 3,4-Dimethoxyphenyl 1.763 3,5-Dimethoxyphenyl 1.764 3,6-Dimethoxyphenyl 1.765 2,3,4-Trimethoxyphenyl 25 1.766 2,3,5-Trimethoxyphenyl 1.767 2,3,6-Trimethoxyphenyl 1.768 2,4,5-Trimethoxyphenyl 1.769 2,4,6-Trimethoxyphenyl 1.770 3,4,5-Trimethoxyphenyl 30 1.771 2-Ethoxyphenyl 1.772 3-Ethoxyphenyl . .
1.773 4-Ethoxyphenyl 1.774 2-iso-Propoxyphenyl 35 1.775 3-iso-Propoxyphenyl 1.776 2-Phenylphenyl 1.777 3-Phenylphenyl 1.778 4-Phenylphenyl 40 1.779 2-Phenoxyphenyl 1.780 3-Phenoxyphenyl 1.781 4-Phenoxyphenyl 1.782 2-Benzyloxyphenyl 1.783 3-Benzyloxyphenyl 1.784 4-Benzyloxyphenyl 1.785 4-(Imidazol-l'-yl)phenyl 0050/45204 - 2 ~ ~ 9 4 2 2 Cvr..~o~nd No. R2 1.786 4-(Piperazin~ yl)phenyl 1.787 4-(Morpholino-l'-yl)phenyl 5 1.788 4-(Piperidinyl-l'-yl)phenyl 1.789 4-(Pyridyl-2'-oxy)phenyl 1.790 2-Cyclopropylphenyl 1.791 3-Cyclopropylphenyl 1.792 4-Cyclopropylphenyl 1.793 3-Cyclohexylphenyl 1.794 4-Cyclohexylphenyl 1.795 4-Oxiranylphenyl 1.796 4-iso-PLopo~y~henyl 15 1.797 3-tert-Butoxyphenyl (1.798 4-tert-~utoxyphenyl 1.799 2-Trifluoromethoxyphenyl 1.800 3-Trifluoromethoxyphenyl 20 1.801 4-TrifluoL~ hoxymethyl 1.802 2-Chloromethylphenyl 1.803 3-Chloromethylphenyl 1.804 4-Chloromethylphenyl 25 1.805 2-Trifluoromethylphenyl 1.806 3-Trifluoromethylphenyl 1.807 4-Trifluoromethylphenyl 1.808 2-(Methoxyiminomethyl)phenyl 1.809 3-(Methoxyiminomethyl)phenyl 30 1.810 4-(Methoxyiminomethyl)phenyl 1.811 2-(Ethoxyiminomethyl)phenyl 1.812 3-(Ethoxyiminomethyl)phenyl 1.813 4-(Ethoxy;m;n~ -thyl)phenyl 35 1.814 2-~n-Propoxyiminomethyl)phenyl 1.815 3-(n-Propoxyiminomethyl)phenyl 1.816 4-(n-Propoxyiminomethyl)phenyl 1.817 2-(iso-Propoxyiminomethyl)phenyl 40 1.818 3-(iso-Propo~yiminomethyl)phen 1.819 2-(Ethoxyimino-1'-ethyl)phenyl 1.820 3-(Ethoxyimino-1'-ethyl)phenyl 1.821 4-(Ethoxyimino-1'-ethyl)phenyl 1.822 2-(n-pLopoxyimino-l~-ethyl)phen 1.823 3-(n-propoxyimino-l~-ethyl)phen 1.824 4-(n-propoxyimino-l'-ethyl)phenyl . , .
~ 2199 i22 Cc"l,~o~nd.No. R2 1.825 2-(n-Butoxyamino-1'-ethyl)phenyl 1.826 3-(n-Butoxyamino-1'-ethyl)phenyl 5 1.827 4-(n-Butoxyamino~ ethyl)phenyl 1.828 2-(n-Pentoxyimino-1'-ethyl)phenyl 1.829 3-(n-Pentoxyimino-1'-ethyl)phenyl 1.830 4-(n-Pentoxyimino-1'-ethyl)phenyl 1.831 2-(n-Hexoxyimino-1'-ethyl)phenyl 1.832 3-(n-Hexoxyimino-1'-ethyl)phenyl 1.833 4-(n-Hexoxyimino~ ethyl)phenyl 1.834 2-(Allyloxyimino-1'-ethyl)phenyl 1.835 3-(Allyloxyimino-1'-ethyl)phenyl 15 1.836 4-(Allyloxyimino-l'-ethyl)phenyl 1.837 2-(Benzyloxyimino-1'-ethyl)phenyl 1.838 3-(Benzyloxyimino-1'-ethyl)phenyl 1.839 4-(Benzyloxyimino-1'-ethyl)phenyl 20 1.840 2-(2-Fluorophenyl)phenyl 1.841 2-(2-Chlorophenyl)phenyl 1.842 2-(2-Methylphenyl)phenyl 1.843 2-(2-Methoxyphenyl)phenyl 25 1.844 4-~iso-~1v~v~y;minomethyl)phenyl 1.845 2-(n-Butoxyiminomethyl)phenyl 1.846 3-(n-Butoxyiminomethyl)phenyl 1.847 4-(n-Butoxyiminomethyl)phenyl 1.848 2-(i~o-Butoxyiminomethyl)phenyl 30 1.849 3-(iso-Butoxyiminomethyl)phenyl 1.850 4-(iso-Butoxyiminomethyl)phenyl 1.851 2-(tert-Butoxyiminomethyl)phenyl 1.852 3-(tert-Butoxyiminomethyl)phenyl 35 1.853 4-(tert-Butoxyiminomethyl)phenyl 1.854 2-(n-Pentoxyiminomethyl)phenyl 1.855 3-(n-Pentoxyiminomethyl)phenyl 1.856 4-(n-Pentoxyiminomethyl)phenyl 40 1.857 2-(n-Hexoxyiminomethyl)phenyl 1.858 3-(n-Hexoxyiminomethyl)phenyl 1.859 4-(n-Hexoxyiminomethyl)phenyl 1.860 2-(Allyloxyiminomethyl)phenyl 1.861 3-(Allyloxyiminomethyl)phenyl 1.862 4-(Allyloxyiminomethyl)phenyl 1.863 2-(Benzyloxyiminomethyl)phenyl 2199~22 Compound No. R2 1.864 3-(Benzyloxyiminomethyl)phenyl 1.865 4-(Benzyloxyiminomethyl)phenyl 5 1.866 2-(Methoxyimino-l'-ethyl)phenyl 1.867 3-(Methoxyimino-1'-ethyl)phenyl 1.868 4-(Methoxyimino-1'-ethyl)phenyl 1.869 3-Phenoxyphenyl 1.870 4-Phenoxyphenyl 1.871 2-Benzyloxyphenyl 1.872 3-BenzyloXyphenyl 1.873 4-Benzyloxyphenyl 1.874 4-(Imidazol-1'-yl)phenyl 15 1.875 4-(Piperazin-l'-yl)phenyl ( 1.876 4-(Morpholin-l'-yl)phenyl 1.877 4-(Piperidin-l'-yl)phenyl 1.878 4-(Pyridyl-2'-oxy)phenyl 20 1.879 2-Cyclopropylphenyl 1.880 3-Cyclopropylphenyl 1.881 4-Cycl~pLo~lphenyl 1.882 3-Cyclohexylphenyl 25 1.883 4-Cyclohexylphenyl 1.884 4-Oxiranylphenyl 1.885 6-F-pyrid-3-yl 1.886 6-C1-pyrid-3-yl 1.887 6-Br-pyrid-3-yl 30 1.888 6-CH3-pyrid-3-yl 1.889 6-CF3-pyrid-3-yl 1.890 6-CH3O-pyrid-3-yl 1.891 2-F-pyrid-4-yl 35 1.892 2-Cl-pyrid-4-yl 1.893 2-Br-pyrid-4-yl 1.894 2-CH3-pyrid-4-yl 1.895 2-CF3-pyrid-4-yl 40 1.896 2-CH30-pyrid-4-yl 1.897 3-F-pyrid-4-yl 1.898 3-Cl-pyrid-4-yl 1.899 3-Br-pyrid-4-yl 1.900 3-CH3-pyrid-4-yl 1.901 3-CF3-pyrid-4-yl 1.902 3-CH30-pyrid-3-yl 0050/45204 2 ~ g 9 1 2 2 C~."p~urld No. R2 1.903 5-F-pyrid-4-yl 1.904 S-Cl-pyrid-4-yl 5 1.905 5-Br-pyrid-4-yl 1.906 5-CH3-pyrid-4-yl 1.907 5-CF3-pyrid-4-yl 1.908 5-CH30-pyrid-4-yl 1.909 6-F-pyrid-4-yl 1.910 6-Cl-pyrid-4-yl 1.911 6-Br-pyrid-4-yl 1.912 6-CH3-pyrid-4-yl 1.913 6-CF3-pyrid-4-yl 15 1.914 6-CH30-pyrid-4-yl ( 1.915 2-F-pyrid-5-yl 1.916 2-Cl-pyrid-5-yl 1.917 2-Br-pyrid-S-yl 20 1.918 2-CH3-pyrid-5-yl 1.919 2-CF3-pyrid-5-yl 1.920 2-CH30-pyrid-5-yl 1.921 4-F-pyrid-5-yl 25 1.922 4-Cl-pyrid-5-yl 1.923 4-Br-pyrid-5-yl 1.924 4-CH3-pyrid-5-yl 1.925 4-CF3-pyrid-5-yl 1.926 4-CH30-pyrid-5-yl 30 1.927 3-F-pyrid-2-yl 1.928 3-Cl-pyrid-2-yl 1.929 3-Br-pyrid-2-yl 1.930 3-CH3-pyrid-2-yl 35 1.931 3-CF3-pyrid-2-yl 1.932 3-CH30-pyrid-2-yl 1.933 4-F-pyrid-2-yl 1.934 4-Br-pyr~d-2-yl 40 1.935 4-CF3-pyrid-2-yl 1.936 4-CH30-pyrid-2-yl 1.937 5-F-pyrid-2-yl 1.938 5-Cl-pyrid-2-yl 1.939 5-Br-pyrid-2-yl 1.940 5-CF3-pyrid-2-yl 1.941 5-CH3-pyrid-2-yl 2199~22 C~h~ d No. R2 1.942 5-CH30-pyrid-2-yl 1.943 6-F-pyrid-2-yl 5 1.944 6-Cl-pyrid-2-yl 1.945 6-Br-pyrid-2-yl 1.946 6-CH3-pyrid-2-yl 1.947 6-CF3-pyrid-2-yl 1.948 6-CH30-pyrid-2-yl 1.949 2-F-pyrid-3-yl 1.950 4-Cl-pyrid-2-yl 1.951 2-Br-pyrid-3-yl 1.952 2-CH3-pyrid-3-yl lS 1.953 2-CF3-pyrid-3-yl .1.954 2-CH30-pyrid-3-yl 1.955 4-F-pyrid-3-yl 1.956 4-Cl-pyrid-3-yl 20 1.957 4-Br-pyrid-3-yl 1.958 4-CH3-pyrid-3-yl 1.95g 4-CF3-pyrid-3-yl 1.960 4-CH30-pyrid-3-yl 25 1.961 S-F-pyrid-3-yl 1.962 S-Cl-pyrid-3-yl 1.963 S-~r-pyrid-3-yl 1.964 S-CH3-pyrid-3-yl 1.965 S-CF3-pyrid-3-yl 30 1.966 5-CH30-pyrid-3-yl 1.967 3-F-5-CF3-pyrid-2-yl 1.968 3,6-C12-S-CF3-pyrid-2-yl 1.969 6-C1-4-C~-pyrid-2-yl 35 1.970 3-CN-5-N02-pyrid-2-yl 1.971 2-Cl-6-F-pyrid-2-yl 1.972 6-Cl-4-F-pyrid-2-yl 1.973 4,6-F2-pyrid-2-yl 40 1.974 3,5-Cl2-6-F-pyrid-2-yl 1.975 6-CH30-3-N02-pyrid-2-yl 1.976 4-CN-6-F-pyrid-2-yl 1.977 6-C1-5-CN-pyrid-2-yl 1.978 6-C1-3-CN-pyrid-2-yl 1.979 6-C1-5-NO2-pyrid-2-yl 1.980 6-Cl-3-N02-pyrid-2-yl 0050/,5204 2 1 9 9 ~ 2 2 Compound No. R2 1.981 5-CN-6-F-pyrid-2-yl 1.982 3-CN-6-F-pyrid-2-yl 5 1.983 4,6-(CN)2-pyrid-2-yl 1.984 S-Br-4-CF3-pyrid-2-yl 1.985 3-N02-5-CF3-pyrid-2-yl 1.986 5-NH2-pyrid-2-yl 1.987 5-N02-pyrid-2-yl 1.988 4-CH3-5-N02-pyrid-2-yl 1.989 2,6-Cl2-pyrid-4-yl 1.990 5-(CH30C0)-pyrid-2-yl 1.991 5-Cl-6-F-pyrid-2-yl 15 1.992 S-Cl-6-011 pyLid-2-yl ( 1.993 S-C1-6-CH30-pyrid-2-yl 1.994 S-Cl-6-CN-pyrid-2-yl 1.995 5,6--C12--pyrid--2--yl 20 1.996 6-Br-5-Cl-pyrid-2-yl 1.997 5-Br-6-F-pyrid-2-yl 1.998 5-Br-6-Cl-pyrid-2-yl 1.999 S-Br-6-CN-pyrid-2-yl 25 1.1000 5-Br-6-OH-pyrid-2-yl 1.1001 5-Br-6-CH30-pyrid-2-yl 1.1002 4-cN-pyrid-2-yl 1.1003 6-CN-pyrid-2-yl 1.1004 S-Cl-pyrid-2-yl 30 1.1005 5-F-pyrid-2-yl ( 1.1006 5-CF3-1,3,4-Thiadiazol-2-yl 1.1007 4-Cl-1,2,5-Thiadiazol-3-yl 1.1008 4-Cl-Pyrimidin-2-yl 35 1.1009 4-Br-Pyrimidin-2-yl 1.1010 4-F-Pyrimidin-2-yl 1.1011 4-CH3-Pyrimidin-2-yl 1.1012 4-CH30-Pyrimidin-2-yl 40 1.1013 4-CH3CH20-Pyrimidin-2-yl 1.1014 4-N02-Pyrimidin-2-yl 1.1015 4-CN-Pyrimidin-2-yl 1.1016 4-CF3-Pyri~idin-2-yl 1.1017 4-C6H5-Pyrimidin-2-yl 1.1018 4-C6H50-Pyrimidin-2-yl 1.1019 5-F-Pyrimidin-2-yl 0050/45204 2 ~ 2 2 C~l..pol~nd No. R2 1.1020 5-CH3-Pyrimidin-2-yl 1.1021 5-CH30-Pyrimidin-2-yl 5 1.1022 5-CH3CH2O-Pyrimidin-2-yl 1.1023 5-NO2-Pyrimidin-2-yl 1.1024 5-CN-Pyrimidin-2-yl 1.1025 5-CF3-Pyrimidin-2-yl 1.1026 5-C6H5-Pyrimidin-2-yl 1.1027 5-C6H5O-Pyrimidin-2-yl 1.1028 4,5-Cl2-Pyrimidin-2-yl 1.1029 4,6-C12-Pyrimidin-2-yl 1.1030 4-Cl-5-CH30-Pyrimidin-2-yl 15 1.1031 2-F-Pyrimidin-4-yl (1.1032 2-Cl-Pyrimidin-4-yl 1.1033 2-F-Pyrimidin-4-yl 1.1034 2-~r-Pyrimidin-4-yl 20 1.1035 2-CH3-Pyrimidin-4-yl 1.1036 2-CH30-Pyrimidin-4-yl 1.1037 2-CH3CH2O-Pyrimidin-4-yl 1.1038 2-NO2-Pyrimidin-4-yl 25 1.1039 2-CH3S-Pyrimidin-4-yl 1.1040 2-Cyano-Pyrimidin-4-yl 1.1041 2-CF3-Pyrimidin-4-yl 1.1042 2-C6H5O-Pyrimidin-4-yl 1.1043 2-C6H5-Pyrimidin-4-yl 30 1.1044 6-NO2-Pyrimidin-4-yl 1.1045 6-Cyano-Pyrimidin-4-yl 1.1046 6-CF3-Pyrimidin-4-yl 1.1047 6-C6H50--Pyrimidin-4-yl 35 1.1048 6-C6H5-Pyrimidin-4-yl 1.1049 5-F-Pyrimidin-4-yl 1.1050 5-Cl-Pyrimidin-4-yl 1.1051 5-Br-Pyrimidin-4-yl 40 1.1052 5-CH3-Pyrimidin-4-yl 1.1053 5-CH30-Pyrimidin-4-yl 1.1054 5--CH3--CH20--Pyrimidin--4--yl 1.1055 5-NO2-Pyrimidin-4-yl 1.1056 5-Cyano-Pyri~idin-4-yl 1.1057 5-CF3-Pyrimidin-4-yl 1.1058 5-C6H5O-Pyrimidin-4-yl 2~99~22 C~L..~oulid No. R2 1.1059 5-C6H5-Pyrimidin-4-yl 1.1060 2-Cl-Pyrimidin-5-yl 5 1.1061 2-CH3-Pyrimidin-5-yl 1.1062 2-F-Pyrimidin-5-yl 1.1063 2-CH30-Pyrimidin-5-yl 1.1064 2-Cyano-Pyrimidin-S-yl 1.106~ 4-CH3-Pyrimidin-5-yl 1.1066 4-CH30-Pyrimidin-5-yl 1.1067 4-CF3-Pyrimidin-5-yl 1.1068 2,4-(CH3)2-Pyrimidin-5-yl 1.1069 2-CH3S-4-CH30-Pyrimidin-5-yl 15 1.1070 Pyrrol-2-yl-6-Cl-3-NO2-pyrid-2-yl 1.1071 6-Cl-3-NO2-pyrid-2-yl 1.1072 6-Cl-5-NO2-pyrid-2-yl 1.1073 3,6-(CH3)2-Pyrazin-2-yl 20 1.1074 6-F-Pyrimidin-4-yl 1.1075 6-Br-Pyrimidin-4-yl 1.1076 6-CH3-Pyrimidin-4-yl 1.1077 6-CH30-Pyrimidin-4-yl 25 1.1078 6-CH3CH2O-Pyrimidin-4-yl 1.1079 4,6-(CH3)2-Pyrimidin-2-yl 1.1080 2-CH3S-6-CH3-Pyrimidin-4-yl 1.1081 2-CH3S-Pyrimidin-4-yl 1.1082 4-C6H50-pyrid-2-yl 30 1.1083 5-C6H5O-pyrid-2-yl 1.1084 6-C6H5O-pyrid-2-yl 1.1085 6-Cl-pyrid-3-yl 1.1086 3,6-(CH3)2-pyrid-2-yl 35 1.1087 4,6-(CH3)2-pyrid-2-yl 1.1088 5,6-(CH3)2-pyrid-2-~l 1.1089 4-C6H5-6-CH3-pyrid-2-yl 1.1090 4,6-(C6H5)2-pyrid-2-yl 40 1.lo9l 3,4-Cl2-6-CH3-pyrid-2-yl 1.1092 3,4,5-Cl3_pyrid-2-yl 1.lOg3 3-CH3CO-4-CH3-pyrid-2-yl 1.1094 3-CH3CO-4,6-(CH3)-pyrid-2-yl 1.1095 3-CH30CO-pyrid-2-yl 1.1096 3-CH30CO-4-CH3-pyrid-2-yl 1.1097 3-CH3-4-Cl-pyrid-2-yl .
.
2 ~ 99422 Compound No. R2 1.1098 3-CH3-5-Cl-pyrid-2-yl 1.1099 3-CH3-6-Cl-pyrid-2-yl 5 1.1100 4-CH3-5-Cl-pyrid-2-yl 1.1101 4-CH3-6-Cl-pyrid-2-yl 1.1102 pyrid-2-yl 1.1103 pyrid-3-yl 1.1104 pyrid-4-yl 1.1105 pyrid-5-yl 1.1106 Pyrimidin-4-yl 1.1107 2-Cl-6-CH3-Pyrimidin-4-yl 1.1108 2,6-Di-Cl-Pyrimidin-4-yl 15 1.1109 2,5,6-Tri-Cl-Pyrimidin-4-yl 1.1110 2-Cl-Pyrimidin-4-yl 1.1111 2-CH3-Thiazol-4-yl 1.1112 1,2,4-Triazin-3-yl 20 1.1113 1,3,5-Triazin-2-yl 1.1114 Pyrazin-2-yl 1.1115 Quinolin-2-yl 1.1116 Quinolin-3-yl 25 1.1117 Pyridazin-3-yl 1.1118 6-Cl-Pyrazin-2-yl 1.1119 6-CH30-Pyrida2in-3-yl 1.1120 6-C1-4-CH3-Pyridazin-3-yl 1.1121 6-Cl-5-CH3-Pyridazin-3-yl 30 1.1122 1,3-Benzthiazol-2-yl (1.1123 Isoquinolin-1-yl 1.1124 Quinolin-4-yl 1.1125 6-Cl-Pyridazin-3-yl 35 1.1126 Pyridazin-4-yl 1.1127 Quinazolin-4-yl 1.1128 7-Cl-Quinolin-4-yl 1.1129 Purin-7-yl 40 1.1130 2-Cl-Purin-7-yl 1.1131 5-NOz-Thien-2-yl 1.1132 Thiazol-2-yl 1.1133 Thiazol-4-yl 1.1134 Thiazol-S-yl 1.1135 oxazol-2-yl 1.1136 Oxazol-4-yl oo~o/45204 2 I g ~ 1 2 2 Cor..~o~,d No. R2 1.1137 Oxazol-5-yl 1.1138 1,2,4-Triazin-5-yl 5 1.1139 1,2,4-Triazin-6-yl 1.1140 6-Cl-Pyrazin-2-yl 1.1141 6-Cl-Pyrazin-3-yl 1.1142 6-C1-Pyridazin-3-yl 1.1143 1,2,4-Triazol-1-yl 1.1144 1,2,3-Triazol-1-yl 1.1145 2-Cl-1~2~4-Oxadiazol-5-yl 1.1146 3-Cl-1, 2 ~ 4-Oxadiazol-S-yl 1.1147 Furan-2-yl 15 1.1148 N-CH3-Pyrrol-2-yl (~1.1149 3-CH3-Ql~;nol; n - 2 - yl 1.1150 4-CH3-Quinolin-2-yl 1.1151 4-C6H5-Quinolin-2-yl 20 1.1152 4-CH3CH2-Quinolin-2-yl 1.1153 6-Cl-Quinolin-2-yl 1.1154 8-CH3-Quinolin-2-yl 1.1155 8-Cl-Quinolin-2-yl 25 1.1156 3,4-(CH3)z-Quinolin-2-yl 1.1157 4-CH3-8-CH30-Quinolin-2-yl 1.1158 4-CH3-8-Cl-~uinolin-2-yl 1.1159 2-CH3-Quinolin-4-yl 1.1160 2-C1-Quinolin-4-yl 30 1.1161 Quinolin-8-yl ( 1.1162 2-CH3-Quinolin-8-yl 1.1163 2-Cl-Quinolin-8-yl 1.1164 2-CH3-6-C1-Quinolin-8-yl 35 1.1165 2-Thiophenyl 1.1166 3-Thiophenyl 1.1167 4-Cl-3-Thiophenyl 1.1168 2-Quinoxazinyl 40 1.1169 2-Furyl 1.1170 3-Furyl 1.1171 1-Pyrrolyl 1.1172 l-Imidazolyl 1.1173 Oxiranyl 1.1174 l-Azetidinyl 1.1175 1-Pyrrolidinyl .
OU50/452~4 ~ 2199 122 Compound No. RZ
1.1176 2-Tetrahydrofuryl 1.1177 2-TetrahydLop~Lanyl 5 1.1178 3-Tetrahydropyranyl 1.1179 l-Piperidinyl 1.1180 l-Morpholidinyl 1.1181 l-Piperazinyl 1.1182 1,3-Dioxan-2-yl 1.1183 CH3-C0 1.1184 CH3CH2-C0 1.1185 n-C3H7-C0 1.1186 iso-C3H7-C0 15 1.1187 n-C4Hg-CO
1.1188 ~ec-C4Hg-CO
1.1189 tert-C4Hg-CO
1.1190 iso-C4-Hg-CO
20 1.1191 CH30-C0 1.1192 CH3CH20-C0 1.1193 n-C3H~0-C0 1.1194 iso-C3H70-C0 25 1.1195 n-C4HgO-CO
1.1196 sec-C4HgO-CO
1.1197 tert-C4HgO-CO
1.1198 iso-C4HgO-CO
1.1199 Phenyl-C0 30 1.1200 2-Fluorophenyl-C0 1.1201 3-Fluorophenyl-C0 1.1202 4-Fluorophenyl-C0 1.1203 Pentafluorophenyl-C0 35 1.1204 2-Chlorophenyl-C0 1.1205 3-Chlorophenyl-C0 1.1206 4-Chlorophenyl-C0 1.1207 Pentachlorophenyl-C0 40 1.1208 2,3-Dichlorophenyl-C0 1.1209 2,4-Dichlorophenyl-C0 1.1210 2,5-Dichlorophenyl-C0 1.1211 2,6-Dichlorophenyl-C0 1.1212 3,4-Dichlorophenyl-C0 1.1213 3,5-Dichlorophenyl-C0 1.1214 2,3,4-Trichlorophenyl-C0 331 2~9~22 Compound No. R2 1.1215 2,3,5-Trichlorophenyl-C0 1.1216 2,3,6-Trichlorophenyl-C0 5 1.1217 2,4,5-Trichlorophenyl-C0 1.1218 2,4,6-Trichlorophenyl-C0 1.1219 3,4,5-Trichlorophenyl-C0 1.1220 2,3,4,6-Tetrachlorophenyl-C0 1.1221 2,3,5,6-Tetrachlorophenyl-Co 1.1222 2-Bromophenyl-C0 1.1223 3-Bromophenyl-C0 1.1224 4-Bromophenyl-C0 1.1225 2,4-Dibromophenyl-C0 lS 1.1226 3-~L._ - ~ fluorophenyl-C0 1.1227 3 - Bll_lc 4-methoxyphenyl-C0 1.1228 2-iodophenyl-C0 1.1229 3-iodophenyl-C0 20 1.1230 4-iodophenyl-C0 1.1231 2-Chloro-4-fluorophenyl-C0 1.1232 2-Chloro-5-fluorophenyl-C0 1.1233 2-Chloro-6-fluorophenyl-C0 25 1.1234 2-Chloro-4-bromophenyl-C0 1.1235 2-Bromo-4-chlorophenyl-C0 1.1236 2-Bromo-4-fluorophenyl-C0 1.1237 3-Bromo-4-chlorophenyl-C0 1.1238 3-Chloro-4-fluorophenyl-C0 30 1.1239 3-Fluoro-4-chlorophenyl-C0 1.1240 2-Cyanophenyl-C0 1.1241 3-Cyanophenyl-C0 1.1242 4-Cyanophenyl-C0 35 1.1243 2-Nitrophenyl-C0 1.1244 3-Nitrophenyl-C0 1.1245 4-Nitrophenyl-C0 1.1246 2-Methylphenyl-C0 40 1.1247 3-Methylphenyl-C0 1.1248 4-Methylphenyl-C0 1.1249 2,4-Dimethylphenyl-C0 1.1250 2,6-Dimethylphenyl-C0 1.1251 3,4-Dimethylphenyl-C0 1.1252 3,5-Dimethylphenyl-C0 1.1253 2,3,4-Trimethylphenyl-C0 Compound No. R2 1.1254 2,3,5-Trimethylphenyl- Co 1.1255 2,3,6-Trimethylphenyl-Co 5 1.1256 2,4,5-Trimethylphenyl-C0 1.1257 2,4,6-Trimethylphenyl-C0 1.1258 3,4,5-Trimethylphenyl-C0 1.1259 6-F-pyrid-3-yl-C0 1.1260 6-Cl-pyrid-3-yl-C0 1.1261 6-Br-pyrid-3-yl-C0 1.1262 6-CH3-pyrid-3-yl-C0 1.1263 6-CF3-pyrid-3-yl-C0 1.1264 6-CH30-pyrid-3-yl-C0 15 1.1265 2-F-pyrid-4-yl-C0 1.1266 2-Cl-pyrid-4-yl-C0 1.1267 2-Br-pyrid-4-yl-C0 1.1268 2-CH3-pyrid-4-yl-C0 20 1.1269 2-CF3-pyrid-4-yl-C0 1.1270 2-CH30-pyrid-4-yl-C0 1.1271 3-F-pyrid-4-yl-C0 1.1272 3-Cl-pyrid-4-yl-C0 25 1.1273 3-Br-pyrid-4-yl-C0 1.1274 3-CH3-pyrid-4-yl-C0 1.1275 3-CF3-pyrid-4-yl-C0 1.1276 3-CH30-pyrid-4-yl-C0 1.1277 5-F-pyrid-4-yl-C0 30 1.1278 5-Cl-pyrid-4-yl-C0 1.1279 5-Br-pyrid-4-yl-C0 1.1280 5-CH3-pyrid-4-yl-C0 1.1281 5-CF3-pyrid-4-yl-C0 35 1.1282 5-CH30-pyrid-4-yl-C0 1.1283 6-F-pyrid-4-yl-C0 1.1284 6-Cl-pyrid-yl-C0 1.1285 6-Br-pyrid-4-yl-C0 40 1-1286 6-CH3-pyrid-4- yl-CO
1.1287 6-CF3-pyrid-4-yl-C0 1.1288 6-CH30-pyrid-4-yl-C0 1.1289 2-F-pyrid-5-yl- CO
1.1290 2-Cl-pyrid-5-yl-C0 1.1291 2-Br-pyrid-5-yl-C0 1.1292 2-CH3-pyrid-5-yl-C0 CG...~v~d No. R2 1.1293 2-CF3-pyrid-5-yl-C0 1.1294 2-CH30-pyrid-5-yl-C0 5 1.1295 4-F-pyrid-5-yl-C0 1.1296 4-Cl-pyrid-5-yl-C0 1.1297 4-Br-pyrid-5-yl-C0 1.1298 4-CH3-pyrid-5-yl-C0 1.1299 4-CF3-pyrid-5-yl-C0 1.1300 4-CH30-pyrid-5-yl-C0 1.1301 3-F-pyrid-2-yl-C0 1.1302 3-Cl-pyrid-2-yl-C0 1.1303 3-Br-pyrid-2-yl-C0 15 1.1304 3-CH3-pyrid-2-yl-C0 1.1305 3-CF3-pyrid-2-yl-C0 1.1306 3-CH30-pyrid-2-yl-C0 1.1307 4-F-pyrid-2-yl-C0 20 1.1308 4-Br-pyrid-2-yl-C0 1.1309 4-CF3-pyrid-2-yl-C0 1.1310 4-CH30-pyrid-2-yl-C0 1.1311 5-F-pyrid-2-yl-C0 25 1.1312 5-Cl-pyrid-2-yl-C0 1.1313 5-Br-pyrid-2-yl-C0 1.1314 5-CF3-pyrid-2-yl-C0 1.1315 5-CH3-pyrid-2-yl-C0 1.1316 5-CH30-pyrid-2-yl-C0 30 1.1317 6-F-pyrid-2-yl-C0 (1.1318 6-Cl-pyrid-2-yl-C0 1.1319 6-Br-pyrid-2-yl-C0 1.1320 6-CH3-pyrid-2-yl-C0 35 1.1321 6-CF3-pyrid-2-yl-C0 1.1322 6-CH30-pyrid-2-yl-C0 1.1323 2-F-pyrid-3-yl-C0 1.1324 2-Cl-pyrid-3-yl-C0 40 1.1325 2-Br-pyrid-3-yl-C0 1.1326 2-CH3_pyrid-3-yl-C0 1.1327 2-CF3_pyrid-3-yl-C0 1.1328 2-CH30-pyrid-3-yl-C0 1.1329 4-F-pyrid-3-yl-C0 1.1330 4-Cl-pyrid-3-yl-C0 1.1331 4-Br-pyrid-3-yl-C0 2199~22 Co..lpound No. R2 1.1332 4-CH30-pyrid-3-yl-C0 1.1333 4-CF3-pyrid-3-yl-C0 5 1.1334 4-CH3-pyrid-3-yl-C0 1.1335 5-F-pyrid-3-yl C0 1.1336 5-C1-pyrid-3-yl-C0 1.1337 5-Br-pyrid-3-yl-C0 1.1338 5-CH3-pyrid-3-yl-C0 1.1339 S-CF3-pyrid-3-yl-C0 1.1340 5-CH30-pyrid-3-yl-C0 Table 1131 Compounds of the general formula I.F (n = 0) in which UR' i5 methoxy, VR" i~ methoxy and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a ~v...poulld corresponding to a group of Table L
~~ Table 1132 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methoxy and Af is the radical -N=CRgRh, Rg being methyl and Rh for a coll,~u~l,d corresponding to a group of Table L
Table 1133 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethoxy and Af i8 the radical -N=CRgRh, R9 being 30 methyl and Rh for a compound corresponding to a group of Table L
Table 1134 Compounds of the general formula I.F (n s 0) in which UR' iB
35 ethoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a cu.,.~ound corresponding to a group of Table L
Table 1135 40 Cv.,-pounds of the general formula I.F (n = 0) in which UR' i8 methylamino, VR" is methoxy and Af is the radical -N=cRsRh~ R9 being methyl and Rh for a compound corresponding to a group of Table L
ooso/45204 2 ~ 9 9 ~ 2 2 Table 1136 Com~o~l~ds of the general formula I.F (n = O ) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N-CRgRh, R9 5 being methyl and Rh for a compound co~responding to a group of Table L
Table 1137 10 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a compound corresponding to a group of Table L
15 Table 1138 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a compound corresponding to a group of Table L
Table 1139 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" i8 methylamino and Af is the radical -N=CR9Rh, R9 25 being methyl and Rh for a compound corresponding to a group of Table L
Table 1140 30 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a compound corresponding to a group of Table L
35 Table 1141 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, Rg being methyl and Rh for a col,.poul,d corresponding to a group of 40 Table L
Table 1142 Compounds of the general formula I.F (n = 0) in which UR' is 45 ethoxy, VR is ethylamino and Af is the radical -N=CRgRh, Rg being methyl and Rh for a cG~.~pound corresponding to a group of Table L
-2199 12~
Table 1143 C~ o~nds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is methoxy and Af is the radical -N=CRgRh, Rg being 5 ethyl and Rh for a co~ o~I,d corresponding to a group of Table L
Table 1144 C~ ounds of the general formula I.F (n = 0) in which UR' is 10 ethoxy, VR" is methoxy and Af is the radical -NsCRgRh, Rg being ethyl and Rh for a ~vl.,p~und corresponding to a group of ~Table L
Table 1145 15 C~ ounds of the general formula I.F (n = 0) in which UR' i8 ! methoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a ~..,p~ d corresponding to a group of Table L
Table 1146 CGr~,~oul,ds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding t~ a group of Table L
25 Table 1147 C~ oullds of the general formula I.F (n 5 0) in which UR' is methyla~ino, VR" is methoxy and Af is the radical -N2CR9Rh, Rg being ethyl and Rh for a cvh.~Gund corresponding to a group of 30 Table L
Table 1148 Compounds of the general formula I.F (n s 0) in which UR' i8 35 ethylamino, VR~ is methoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1149 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, R9 being ethyl and Rh for a compound corresponding to a group of Table L
21g9~22 Table 1150 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being 5 ethyl and Rh for a compound corresponding to a group of Table L
Table 1151 Co...p~u~lds of the general formula I.F (n z 0) in which UR' is 10 methoxy, VR~' i8 methylamino and Af is the radical -N=CRgRh, R9 being ethyl and Rh for a c~ und corresponding to a group of Table L
Table 1152 ! Co.,.~vu~ds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1153 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 25 being ethyl and Rh for a cvm~oulld corresponding to a group of Table L
Table 1154 30 Compounds of the general formula I.F (n = 0) in which UR' i5 ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1155 Compounds of the general formula I.F tn = 0) in which UR' is methoxy, VR" is methoxy and Af is the radical -N~CRgRh, Rg being n-propyl and Rh for a c :EouLLd corresponding to a group of Table L
40 Table 1156 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VRn is methoxy and Af is the radical -N=CRgRh, Rq being n-propyl and Rh for a compound corresponding to a group of Table L
2199~22 ~able 1157 Compounds of the general formula I.F (n = 0) in which UR' iB
methoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being 5 n-propyl and Rh for a compound corresponding to a group of Table L
Table 1158 Co~.,poUnds of the general formula I.F (n = 0) in which UR' is 10 ethoxy, VRn is ethoxy and Af is the radical -N=CR9Rh, Rg being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1159 15 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VRn is methoxy and Af i5 the radical -N=CR9Rh, R9 being n-propyl and Rh for a ~ol~,kvund corresponding to a group of Table L
20 Table 1160 CG,..~unds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 being n-propyl and Rh for a compo~nd corresponding to a group of 25 Table L
Table 1161 Compounds of the general formula I.F (n = 0) in which UR' is 30 methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being n-propyl and Rh for a cv..,~ul.d corresponding to a group of Table L
Table 1162 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -~=CRgRh, R9 being n-propyl and Rh for a compound corresponding to a group of Table L
40 Table 1163 Compounds of the general f ormula I.F (n = 0) in which UR' i8 methoxy, VR" is methylamino and Af is the radical -N2CRgRh, R9 being n-propyl and Rh for a co",pound corresponding to a group of 45 Table L
2199~22 Table 1164 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rq 5 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1165 10 C~,ll~ou--ds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being n-propyl and Rh for a c~ ound corresponding to a group of Table L
15 Table 1166 ~' Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, R9 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1167 Compounds of the general formula I.F (n = 0) in which UR' i5 methoxy, VR" is methoxy and Af is the radical -N=CR9Rh, R9 being 25 cyclopropyl and Rh for a c~lupound correspo~ng to a group of Table L
Table 1168 30 Compounds of the general formula I.F (n ~ 0) in which UR' i~
ethoxy, VR" is methoxy and Af is the radical -N=CR9Rh, Rg being cyclopropyl and Rh for a compound corresponding to a group of Table L
35 Table 1169 Compounds of the general formula I.F (n e o) in ~hich UR' is methoxy, VR" is ethoxy and Af is the radical -NsCR9Rh, Rg being cyclopropyl and Rh for a cG..*ound corresponding to a group of 40 Table L
-2Ig9!!22 Table 1170 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being S cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1171 10 Compounds of the general formula I.F (n - 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 being cyclopropyl and Rh for a c~ _ound corresponding to a group of Table L
15 Table 1172 ¢
Compounds o~ the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af i8 the radical -N=CRgRh, Rg being cyclopropyl and Rh for a c~ -und corresponding to a group 20 of Table L
Table 1173 Compounds of the general formula I.F (n = 0) in which UR' is 25 methylamino, VR" is ethoxy and Af i8 the radical -N=CR9Rh, Rg being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1174 CG..*o~nds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af iS the radical -N=CR9Rh, R9 being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1175 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VRn is methylamino and Af is the radical -N=CRgRh, R9 40 being cyclopropyl and Rh for a compound corresponding to a group of Table L
0050t45204 2199~22 Table 1176 Compounds of the general formula I.F (n = 0) in which UR' i5 ethoxy, VRn is methylamino and Af is the radical -N=CRgRh, Rg 5 being cyclopropyl and Rh for a compound corresponding to a group of Table L
Table 1177 10 Compounds of the general formula I.F (n = 0) in which UR' i8 methoxy, VR" i8 ethylamino and Af is the radical -N=CRgRh, Rg being cyclopropyl and Rh for a cG...~ouild corresponding to a group of Table L
15 Table 1178 ( Cv...pounds of the general formula I.F (n = 0) in which UR' i8 ethoxy, VRn is ethylamino and Af is the radical -N=CRgRh, Rg being cyclopropyl and Rh for a compound corresponding to a group of 20 Table L
Table 1179 Compounds of the general formula I.F (n = 0) in which UR' is 25 methoxy, VRn is methoxy and Af is the radical -N=CRqRh, Rg being CF3 and Rh for a cGm~o~nd corresponding to a group of Table L
Table 1180 30 co.,~u"ds of the general formula I.F (n = 0) in which UR' i8 ethoxy, VR" is methoxy and Af is the radical -N-CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
Table 1181 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR~ is ethoxy and Af is the radical -N=C~RgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
40 Table 1182 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR~' is ethoxy and Af is the radical -N=CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
-~able 1183 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, Rg 5 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1184 10 Compounds of the general formula I~F (n = 0) in which UR' is ethylamino, VR" i8 methoxy and Af is the radical -N=CRgRh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
15 Table 1185 ( Compounds of the general formula I.F (n 3 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CR9Rh, Rg being CF3 and Rh for a compound corresponding to a group of Table Table 1186 Compounds of the general formula I.F (n z 0) in which UR' is 25 ethylamino, VR" is ethoxy and Af is the radical -N=CRgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1187 30 Compounds of the general formula I.F (n = 0) in which UR' i~
methoxy, VR" is methylamino and Af is the radical -N=cRsRh~ Rs being CF3 and Rh for a compound corresponding to a group of Table L
35 Table 1188 Compounds of the general formula I.F (n = o) in which UR' is ethoxy, VR" is methylamino and Af is the radical -N=CRgRh, R9 being CF3 and Rh for a compound corresponding to a group of Table ~ 2199~22 Table 1189 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 5 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1190 10 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CR9Rh~ Rg being CF3 and Rh for a compound corrQsponding to a group o~ Table L
Table 1191 Co,-,~ou~-ds of the general formula I.F (n = 0) in which UR' is methoxy, VRn is methoxy and Af i8 the radical -N=CRgRh, Rg being methylthio and Rh for a co...~Gulld corresponding to a group of Table L
~ 20 Table 1192 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methoxy and Af i~ the radical -N=CR9Rh, Rg being 25 methylthio and Rh for a cv~ ound corresponding to a group of Table L
Table 1193 30 Compound~ of the general formula I.F (n = 0) in which UR' is f methoxy, VR" is ethoxy and Af is the radical -N=CR9Rh, Rs being ~ methylthio and Rh for a compound corresponding to a group of Table L
35 Table 1194 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -N=CRgRh, R9 being methylthio and Rh for a cv...~Gul~d corresponding to a group of Table .
21g9~2 Table 1195 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 5 being methylthio and Rh for a compound corresponding to a group of Table L
Table 1196 10 C~."~ounds of the general formula I.F (n - 0) in which UR' is ethylamino, VR" is methoxy and Af i5 the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
15 Table 1197 ( Compounds of the general formula I.F (n 2 o) in which UR' is methylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, Rg being methylthio and Rh ~or a c po~nd corresponding to a group of 20 Table L
Table 1198 Compounds of the general formula I.F (n - 0) in which UR' i5 25 ethylamino, VR" i8 ethoxy and Af is the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
Table 1199 C~...pouilds of the general formula I.F (n S 0) in which UR~ is methoxy, VRn is methylamino and Af is the radical -N=CR9Rh, R9 being methylthio and Rh for a compound corresponding to a group of Table L
Table 1200 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" i8 methylamino and Af is the radical -NsCRgRh, R9 40 being methylthio and Rh for a compound corresponding to a group of Table L
.
2I9g422 3g5 Table 1201 Compounds of the general formula I.F (n ~ 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg 5 being methylthio and Rh for a cull*oul,d corresponding to a group of Table L
Table 1202 10 CG..~ounds of the general formula I.F (n - 0) in which UR' is ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being methylthio and Rh for a compound corresponding to a group of Table L
15 Table 1203 Compounds of the general formula I.F (n = 0) in which UR' i8 methoxy, VR" is methoxy and Af i8 the radical -N-CRgRh, R9 being cyano and Rh for a c~l"~ound corresponding to a group of Table L
Table 1204 Compounds of the general formula I.F ~n - 0) in which UR' i8 ethoxy, VR" i8 methoxy and Af is the radical -N=CR9Rh, R9 being 25 cyano and Rh for a c~.,.~ound corresponding to a group of Table L
Table 1205 Compounds of the general formula I.F (n = 0) in which UR' is 30 methoxy, VR~' is ethoxy and Af is the radical -N=CR9Rh, R9 being cyano and Rh for a co,-.pound corresponding to a group of Table L
Table 1206 35 Co~ o~L.ds of the general formula I.F (n 5 O) in which UR' is ethoxy, VR" is ethoxy and Af is the radical -NsCR9Rh, Rq being cyano and Rh for a co,ll~oul-d corresponding to a g~oup of Table L
Table 1207 C~,..pounds of the general formula I.F (n = 0) in which UR' i8 methylamino, VR" is methoxy and Af is the radical -N=CRgRh, Rg being cyano and Rh for a c~ _ und corresponding to a group of Table L
2199~22 Table 1208 Compounds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 5 being cyano and Rh for a compound corresponding to a group of Table L
Table 1209 10 Compounds of the general formula I.F (n = 0) in which UR' is methylamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being cyano and Rh for a compound corresponding to a group of Table L
15 Table 1210 ( Co,-.~oUnds of the general formula I.F (n = 0) in which UR' is ethylamino, VR" is ethoxy and Af is the radical -N=CR~Rh, Rg being cyano and Rh for a cv..~oulld corresponding to a group of Table Table 1211 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is methylamino and Af is the radical -N=CRgRh, Rg 25 being cyano and Rh for a ~v.ll~ound corresponding to a group of Table L
Table 1212 30 Compounds of the general formula I.F (n = 0) in which UR' is ethoxy, VR" is methylamino and A~ is the radical -N=CR9Rh, R9 ~~ being cyano and Rh for a co,llpound corresponding to a group of Table L
35 Table 1213 Compounds of the general formula I.F (n = 0) in which UR' is methoxy, VR" is ethylamino and Af is the radical -N=CR9Rh, Rg being cyano and Rh for a compound corresponding to a group of 40 Table L
Table 1214 Compounds of the general formula I.F (n = 0) in which UR~ is 45 ethoxy, VR" is ethylamino and Af is the radical -N=CRgRh, Rg being cyano and Rh for a compound corresponding to a group of Table L
~199~22 Table L
No. Rh C6Hs 5 2 2-Cl-C6H4 3 3-Cl-C6H4 4 4-Cl-C6H4 2,4-Clz-C6H3 10 6 2,5-Clz-C6H3 7 2,6-Cl2-C6H3 8 3,4-C12-C6H3 9 2-Br-C6H4 3-Br-C6H4 15 11 4-~r-C6H4 18 2,4-~CH3)2-C6H3 25 19 2,5-(CH3)2-C6H3 2,6-(CH3)2-C6H3 21 3,4-(CH3)2-C6H3 22 2-CH(CH3)2-C6H4 30 23 3-CH(CH3)z-C6H4 24 4-CH(CH3)2-C6H4 ( 25 2-c(cH3)3-c6H4 26 3-C(CH3)3-C6H4 27 4-C(CH3)3-C6H4 35 28 3-CH3, 4-C(CH3)3-C6H3 29 4-CH3, 3-C(CH3)3-C6H3 33 2-OCH(CH3)z-C6H4 34 3-OCH(CH3)2-C6H4 4-OCH(CH3)z~C6H4 45 36 2-OC(CH3)3-C6H4 37 3-OC(CH3)3-C6H4 38 4-OC(CH3)3-C6H4 2~99 122 No. Rh 43 3-ocF3-C6H4 44 - 4-oCF3-C6H4 2-sc(cH3)3-c6H4 46 3-SC(CH3)3-C6H4 47 4-sc(cH3)3-C6H4 51 3-C(CH3)2NOCH3-C6H4 52 4-C(CH3)=NOCH3-C6H4 53 2-CH3, 4-C(CH3)2NOCH3-C6H3 20 54 2,5-(CH3)2, 4-C(CH3)=NOCH3-C6Hz 2-CH3, 5-Cl-C6H3 56 5-CH3, 2-Cl-C6H3 57 2,3,4-C13-C6H2 3,4,5-C13-C6H2 62 CH(cH3) 2 63 C(CH3)2-O-CH3 64 C(CH3)z-O-CH2CH3 Cyclopropyl 66 Cyclopentyl 35 67 Cyclohexyl 68 l-Naphthyl 69 2-Naphthyl 2-Pyridyl 40 71 3-Pyridyl 72 4-Pyridyl 73 2-Thienyl 74 3-Thienyl 45 75 5-Cl-Thien-2-yl 76 5-Cl-Thien-3-yl 77 2-Furyl 2I 99~ 22 No. Rh 78 3-Furyl 79 2-Pyrimidinyl 5 80 4-Pyrimidinyl 81 5-Pyrimidinyl 82 4-OC2H5-pyrimidin-2-yl 83 2-Pyrazinyl Table 1215 CG".~o~,lds of the general formula I.G (n = 0) in which UR' is methoxy, VR" is methoxy, Y9 is oxygen and A9 for a compound 15 corresponds to a group of Table M
Table 1216 Compounds of the general formula I.G (n a O) in which UR' i8 20 ethoxy, VR" is methoxy, Yg is oxygen and Ag for a co...~ound corresponds to a group of Table M
Table 1217 25 C ~ounds of the general formula I.G (n 8 O) in which UR' is methoxy, VR" is eth~xy, Yg is oxygen and Ag for a compound corresponds to a group of Table M
Table 1218 ' Compounds of the general formula I.G (n = 0) in which UR' is ethoxy, VRN is ethoxy, Y9 is oxygen and A9 for a cor..~ound corresponds to a group of Table M
35 Table 1219 Cor..pounds of the general formula I.G (n = 0) in ~hich UR' i5 methylamino, VR~' is methoxy, Yg is oxygen and Ag for a cGr..~und corresponds to a group of Table M
Table 1220 ~
Compounds of the general formula I.G (n = 0) in which UR' is ethylamino, VR~' is methoxy, Yg is oxygen and A9 for a ~on,~oul-d 45 corresponds to a group of Table M
~ 2199~22 Table 1221 Compounds of the general formula I.G (n = 0) in which UR' is methylamino, VRn iS ethoxy, Yg is oxygen and A9 for a cv.,.~o~lld 5 corresponds to a group of Table M
Table 1222 Compounds of the general formula I.G (n - 0) in wh~ch UR' is 10 ethylamino, VRn i8 ethoxy, Y9 is oxygen and Ag for a compound corresponds to a group of Table M
Table 1223 15 Co...pounds of the general formula I.G ~n = 0) in which UR' is methoxy, VR" is methylamino, Y9 is oxygen and Ag for a co...poul.d corresponds to a group of Table M
Table 1224 Compounds of the general formula I.G ~n = 0) in which UR' is ethoxy, VRn is methylamino, Yg is oxygen and Ag for a compound corresponds to a group of Table M
25 Table 1225 Compounds of the general formula I.G (n = 0) in which UR' is methoxy, VRn iS ethylamino, Yg i8 oxygen and Ag for a compound corresponds to a group of Table M
Table 1226 C unds of the general formula I.G (n = 0) in which UR' is ethoxy, VR" i8 ethylamino, Yg is oxygen and Ag for a ~ v~nd 35 corresponds to a group of Table M
Table M .
No. Ag 40 1 C6Hs 2 2-Cl-C6H4 3 3-Cl-C6H4 4 4-Cl-C6H4 45 5 2,4-Cl2-C6H3 6 2,5-Cl2-C6H3 7 2,6-Cl2-C6H3 -0050~45~04 ~ 351 2199~22 No. . Ag 8 3,4-Cl2-c6H3 12 2,4-(CH3)2-C6H3 13 2,5-(CH3)2-C6H3 2,6-(CH3)2-C6H3 3,4-(CH3)2-C6H3 16 2-Cl, 5-CH3-C6H3 17 5-Cl, 2-CH3-C6H3 3-oC6Hs~C6H4 26 4-oC6H5-C6H4 ( 33 4-Br, 3-CF3-C6H3 34 4-Cl, 3-OCH3-C6H3 3~4-~OCHzO]-C6H3 36 2-cl, 3,4-tOCH2O]-C6H2 0 40 CH(cH3)2 41 CH2cH2cH2cH3 42 CH(CH3)CH2CH3 43 CH2CH(CH3) 2 44 C(CH3)3 46 Cyclopropyl 0050~45204 Z199~22 No. Ag 47 Cyclopentyl ~ 48 Cyclohexyl 49 CH=CHCH3 C-C-C(CH3)3 51 1-Naphthyl 52 2-Naphthyl 53 2-CH3-thiazol-4-yl 54 2-CH(CH3)2-thiazol-4-yl 2-CF3-thiazol-4-yl 56 2-OCH3-thiazol-4-yl 57 2-SCH3-thiazol-4-yl 15 58 2-NHCH3-thiazol-4-yl ( 59 2-N~CH3)2-thiazol-4-yl 2-C6H5-thiazol-4-yl 61 2-(4-OCF3-C6H4)-thiazol-4-yl 20 62 C6Hs-C(sO) 63 2-Cl-C6H4-C(=O) 64 3-Cl-C6H4-C(=O) 4-Cl-C6H4-C(=O) 25 66 2,4-Cl2-C6H3-C(=o) 67 2,5-Cl2-C6H3-C(=O) 68 2,6-Cl2-C6H3-C(=O) 69 3,4-Cl2-C6H3-C(=O) 2-CH3-C6H4-C(=O) 30 71 3-CH3-C6H4-C(=O) ( 72 4-CH3-C6H4-C(=O) 73 2,4-(CH3)2-C6H3-C(=O) 74 2,5-(CH3)2-C6H3-C(=O) 35 75 2,6-(CH3)2-C6H3-c(=O) 76 3,4-(CH3)2-C6H3-C(=O) 77 2-Cl, 5-CH3-C6H3-C(=O) 78 5-Cl, 2-CH3-C6H3-C(=O) 40 79 2-OCH3-C6H4-C(=O) 8 0 3--OCH3--C6H4--C ( =O ) 81 4-OCH3-C6H4-C(sO) 82 2-C6Hs~C6H4~c(sO) 45 83 3-C6Hs-c6H4-c(=O) 84 4-C6H5-C6H4-C(=O) 2-OC6H5-C6H4-C(=o) _ ~ 9422 No. A9 86 3-OC6H5-C6H4-C(=O) 87 4-OC6Hs-C6H4-C( 20 ) 5 88 2-Noz-c6H4-c(=o) 89 3-NO2-C6H4-C( 80 ) g o 4--~o2-c6H4--c ( =o ) 91 2-CN-C6H4-C(=O) 10 92 3-CN-C6H4-C(=O) 93 4-CN-C6H4-C(=O) 94 4-Br, 3-CF3-C6H3-C(-O) 9S 4-Cl, 3-OCH3-C6H3-C~-O) 96 C6H5-CH(OH)-15 97 2-Cl-C6H4-CH(OH)-98 3-Cl-C6H4-CH(OH)-99 4-Cl-C6H4-CH(OH)-100 2,4-Cl2-C6H3-CH(OH)-20 101 2,5-Cl2-C6H3-CH~OH)-102 2,6-Cl2-C6H3-CH(OH)-103 3,4-Clz-C6H3-CH(OH)-104 2-CH3-C6H4-CH(OH)-25 105 3-CH3-C6H4-CH(OH)-106 4-CH3-C6H4-CH(OH)-107 2,4-(CH3)z-C6H3-CH(OH)-108 2~5-(cH3)2-c6H3-cH(oH)-109 2,6--(CH3)z--C6H3--CH(OH)--110 3,4-(CH3)2--C6H3--CH(OH)--111 2-Cl, 5-CH3-C6H3-CH(OH)-112 5-Cl, 2-CH3-C6H3-~H(OH)-113 2-OCH3-C6H4-CH(OH)-35 114 3-OCH3-C6H4-CH(OH)-115 4-OCH3-C6H4-CH(OH)-116 2-C6H5-C6H4-CH(OH)-117 3-C6Hs-C6H4-CH(OH)-40 118 4-C6H5-C6H4-CH(OH)-119 2-OC6H5-C6H4-CH(OH)-120 3-OC6HS-C6H4-CH(OH)-121 4-OC6H5-C6H4-CH(OH)-45 122 2-NO2-C6H4-CH(OH)-123 3-NO2-C6H4-CH(OH)-124 4-N02-C6H4-CH(OH)-2199~22 No. A9 125 2-CN-C6H4-CH(OH)-126 3-CN-C6H4-CH(OH)-5 127 4-CN-C6H4-CH(OH)-128 4-Br, 3-CF3-C6H3-CH(OH)-129 4-Cl, 3-OCH3-C6H3-CH(OH)-10 Table 1227 Compounds of the ~eneral formula I.H (n - m 8 ~) ~n which UR' is methoxy, VR" i~ methoxy and Ah for a compound corresponds to a group of Table N
Table 1228 Compounds of the general formula I.H (n = m ~ O) in which UR' is ethoxy, VR" is methoxy and Ah for a cv~ ound corresponds to a 20 group of Table N
Table 1229 Compounds of the general formula I.H (n = m = O) in which UR' is 25 methoxy, VRn is ethoxy and Ah for a oo-"~ound corresponds to a group of Table N
Table 1230 30 Compounds of the general formula I.H (n - m = O) in which UR' is ethoxy, VR" is ethoxy and Ah for a ~",~ound corresponds to a group of Table N
Table 1231 Compounds of the general formula I.H (n = m = O) in which UR' is methylamino, VR" is methoxy and Ah for a compound corresponds to a group of Table N
40 Table 1232 Compounds of the general formula I.H (n = m = O) in which UR' is ethylamino, VR" is methoxy and Ah for a c~ ound corresponds to a group of Table N
U(15~ !lJ4 355 2 1 9 9 ~ 2 2 Table 1233 . .
Co...~ou,lds of the general formula I.H (n = m = 0) in which UR' is methylamino, VR" is ethoxy and Ah for a compound corresponds to a 5 group of Table N
Table 1234 Compounds of the general formula I.H (n = m = 0) in which UR' is 10 ethylamino, VR" is ethoxy and Ah for a co,..pound corresponds to a group of Table N
Table 1235 15 C _ unds o~ the general formula I.H (n - m = 0) in which UR' i8 methoxy, VR" is methylamino and Ah for a compound corresponds to a group of Table N
Table 1236 ~ 20 Compounds of the general formula I.H (n = m = 0) in which UR' is ethoxy, VR" is methylamino and Ah for a compound corresponds to a group of Table N
25 Table 1237 Compounds of the general formula I.H (n = m = 0) in which UR' is methoxy, VR" is ethylamino and Ah for a compound correspond~ to a group of Table N
Table 1238 Compounds of the general formula I.H (n = m = 0) in which UR' is ethoxy, VR~ is ethylamino and Ah for a compound corresponds to a 35 group of Table N
Table N
No. Ah 40 1 Br 2~9~22 No. Ah 9 C ( CH3 ) =NOCH3 12 CO2C(CH3)3 C--C-C(CH3)3 16 C----C-Si(CH3)3 2 0 C6H5--OcH2 24 2-F--C6H4-cH2o 2 6 2-F--C6H4--CH=CH--2 7 2--F--C6H4-C _ C--3 o 3-F--C6H4--OcH2 31 3--F--C6H4--CH=CH--3 5 4-F-C6H4--OcH2 38 2-Cl--C6H4 3 9 2--Cl--C6H4--cH2o 2--Cl--C6H4--ocH2 41 2-Cl--C6H4--CH=CH--4 2 2-Cl--C6H4-C = C--43 3-Cl--C6H4 44 3-Cl--C6H4--cH2o 3-Cl--c6H4-ocH2 4 6 3-Cl--C6H4-CH=CH--~199122 No. . Ah 47 3-Cl-C6H4-C 8 C-4B 4-Cl-C6H4 5 49 4-cl-c6H4-cH2o 4-cl-c6H4-ocH2 51 4-Cl-C6H4-CH=CH-52 4-Cl-C6H4-CoC~
2,4-Cl2-C6H3 54 2,4-Cl2-C6H3-CH20 2,4-cl2-c6H3-ocH2 56 2,4-Cl2-C6H3-CH=CH-57 2,4-Cl2-C6H3-C-C-15 58 2,5-Cl2-C6H3 59 2,5-cl2-c6H3-cH2o 2,5-cl2-c6H3-ocH2 61 2,5-Cl2-C6H3-CH=CH-20 62 2,5-Cl2-C6H3-C8C-63 2,6-Cl2-C6H3 64 2,6-cl2-c6H3-cH2o 2,6-C12-C6H3-0CH2 25 66 2,6-Cl2-C6H3-CH=CH-67 2,6-Cl2-C6H3-C 8C -68 3,4-Cl2-C6H3 69 3,4-Cl2-C6H3-CH20 3,4-Cl2-C6H3-0CH2 71 3,4-Cl2-C6H3-CH=CH-72 3,4-Cl2-C6H3-C8C-76 2-CH3-C6H4-CH=CH-81 3-CH3-C6H4-CH=CH-- -v v ~ u ~
2199~22 No. Ah 86 4-CH3-C6H4-CH=CH-5 88 2,4-(CH3)2-C6H3 89 2,4-(CH3)2-C6H3-CH2O
go 2,4-(CH3)2-C6H3-OCH2 91 2,4-(CH3)2-C6H3-CH=CH-lO 92 2,4-(CH3)2-C6H3-C-C-93 2,5-(CH3)2-C6H3 94 2,5-(CH3)2-C6H3-CH20 2,5-(CH3)2-C6H3-0CH2 96 2,5-(CH3)2-C6H3-CH=CH-97 2,5-(CH3)2-C6H3-C-C-98 2,6-(CH3)2-C6H3 99 2,6-(CH3)2-C6H3-CH20 100 2,6-~CH3)2-C6H3-0cH2 20 101 2,6-(CH3)2-C6H3-CH=CH-102 2,6-(CH3)2-C6H3-C-C-103 3,4-(CH3)2-C6H3 104 3~4-(CH3)2-c6H3-cH20 25 105 3,4-(CH3)2-C6H3-OCH2 106 3,4-(CH3)2-C6H3-CH=CH-107 3,4-(CH3)2-C6H3-C-C-108 2-CH3, 5-Cl-C6H3 109 2-CH3, 5-Cl-C6H3-CH2O
30 110 2-CH3, 5-Cl-C6H3-OCH2 111 2-CH3, 5-Cl-C6H3-CH=CH-112 2-CH3, 5-Cl-C6H3-CaC-113 5-CH3, 2-Cl-C6H3 35 114 5-CH3, 2-Cl-c6H3-cH2O
115 5-CH3, 2-cl-c6H3-ocH2 -116 5-CH3, 2-Cl-C6H3-CH=CH-117 5-CH3, 2-cl-C6H3-CaC-124 3-OCH3-C6H4-cH2O
0050/45204 2 ~ 9 9 ~ 2 2 35g No. Ah 125 3-OCH3-C6H4-OCHz 126 3-OCH3-C6H4-CH=CH-5 127 3-OCH3-C6H4-C_C-129 4-OCH3-C6H4-cH20 130 4-OCH3-C6H4-0cH2 10 131 4-OCH3-C6H4-CH=CH-134 2-CN-C6H4-cH20 135 2-CN-C6H4-0cH2 15 136 2-CN-C6H4-CH=CH-137 2-CN-C6H4-C_C-139 3-CN-C6H4-cH20 141 3-CN-C6H4-CH=CH-142 3-CN-C6H4-CaC-25 144 4-CN-C6H4-cH20 146 4-CN-C6H4-CH=CH-147 4-CN-C6H4-C_C-148 4-oc6H4-C6H4 149 4-OC6H4-C6H4-cH20 ~=
f'150 4--OC6H4--C6H4--OCH2 151 4-OC6H4-C6H4-CH=CH-152 4-OC6H~-C6H4-C=C-35 153 2-Pyridyl lS4 3-Pyridyl 155 4-Pyridyl 156 4-Pyridyl-C-C-40 157 2-Pyrimidyl 158 4-Pyrimidyl 159 5-Pyrimidyl 160 2-Thienyl 45 161 3-Thienyl 162 5-Cl-2-thienyl 163 2-Furyl -~U5U/ 4S~4 2199~22 No. Ah 164 3-Furyl 165 2-Thiazolyl 5 166 4-Thiazolyl 167 2-CH3-thiazol-4-yl 16B 2-CH~CH3)2-thiazol-4-yl 169 2-C~CH3)3-thiazol-4-yl 10 170 2-OCH3-thiazol-4-yl 171 2-CF3-thiazol-4-yl 172 2-SCH3-thiazol-4-yl 173 2-N(CH3)2-thiazol-4-yl 174 2-C6H5-thiazol-4-yl 15 175 2-(4-F-C6H4)-thiazol-4-yl 176 2-(4-CH3-C6H4)-thiazol-4-yl 177 2-(4-CF3-C6H4)'-thiazol-4-yl 178 2-(4-ocH3-c6H4)-thiazol-4 20 179 2-(4-OCF3-C6H4)-thiazol-4-yl 180 2-~3,4-(OCH20)-C6H3]-thiazol-4-yl 181 2-S(=O)CH3-thiazol-4-yl 182 2-t2-CH2CH3-thiazol-4-yl]-thiazol-4-yl 25 183 2-[2-CH(CH3)z-thiazol-4-yl]-thiazol-4-yl 184 2-[2-C(CH3)3-thiazol-4-yl]-~ h; A 7~1 - 4-yl 185 5-NO2-thiazol-2-yl 186 4-~4-F-C6H4), 5-CH3-thiazol-2-yl 187 Isoxazol-5-yl 30 188 3-CH3-isoxazol-5-yl 189 3-CH(CH3)2-isoxazol-5-yl 190 3-C(CH3)3-isoxazol-5-yl 191 3-(CH2)4CH3-isoxa201-5-yl 35 192 3-[CH(CH3)CH2CH2CH3]-isoxazol-5-yl 193 3-CF3-isoxazol-5-yl 194 3-OCH3-isoxazol-5-yl .
195 3-C6H5-isoxazol-5-yl 40 196 3-(4-F-C6H4)-isoxa201-5-yl 197 3-(3~4-Cl2-C6H3)-isoxazol-5-yl 198 3-(4-CH3-C6H4)-isoxazol-5-yl 199 3-(4-CF3-C6H4)-isoxazol-5-yl 45 200 3-(4-OCH3-C6H4)-isoxazol-5-yl 201 3-(4-OCF3-C6H4)-isoxazol-5-yl 202 5-CH3-1,2,4-oxadiazol-3-yl 0050~45204 2~99~22 No. Ah 203 5-CF3-1,2,4-oxadiazol-3-yl 204 5-CH3-1,3,4-thiadiazol-2-yl 5 205 5-CF3-1,3,4-thiadiazol-2-yl Table 1239 Compounds of the general formula I.K (n = 0) in which UR' is 10 methoxy, VRn is methoxy, Rf is hydrogen and the combination of the substituents R~, Rd and Ak corresponds for each co...~ouid to a line of Table 0 Table 1240 Ccr..~uul,ds of the general for~t-l~ I.K (n = 0) in which UR' is ethoxy, VR~ i8 methoxy, Rf is hydrogen and the combination of the substituents Re~ Rd and Ak corresponds for each cv...~ound to a line of Table 0 Table 1241 Compounds of the general formula I.K (n = 0) in which UR' is methoxy, VR" is ethoxy, Rf is hydrogen and the comh~n~tion of the 25 substituents Re, Rd and Ak corresponds for each c~ und to a line of Table 0 Table 1242 30 Compounds of the general formula I.K (n = 0) in which UR' is . ethoxy, VR" is ethoxy, Rf is hydrogen and the combination of the f substituents R~, Rd and Ak corresponds for each c~ ound to a line of Table 0 35 Table 1243 Compounds of the general formula I.K (n = 0) in wh~ch UR' is methylamino, VRn is methoxy, Rf is hydrogen and the combination of the substituents Re, Rd and Ak corresponds for each compound to a 40 line of Table o ~JU3U~ ~v~
~ 2199~22 Table 1244 Compounds of the general formula I.K (n - 0) in which UR' is ethylamino, VR" is methoxy, Rf is hydrogen and the c~mh;n~tion of 5 the substituents Rer Rd and Ak corresponds for each compound to a line of Table 0 Table 1245 10 Cvm~oullds of the general formula I.K (n = 0) in which UR' is methylamino, VRn is ethoxy, Rf is hydrogen and the combination of the substituents R~, Rd and Ak correspond~ ~or each cor.~und to a line of Table o 15 Table 1246 ( Compounds of the general formula I.K (n = 0) in which UR' is ethylamino, VR" is ethoxy, Rf is hydrogen and the combination of the substituents RQ, Rd and Ak corresponds for each co,l.pound to a 20 line o~ Table 0 Table 1247 Co..,~v~nds of the general formula I.K (n = 0) in which UR' is 25 methoxy, VR" is methylamino, Rf i5 hydrogen and the combination of the substituents Re~ Rd and Ak corresponds for each compound to a line of Table 0 Table 1248 Compounds of the general formula I.K (n = 0) in which UR' ls ethoxy, VR" is methylamino, Rf is hydrogen and the c~h; n~tion of the substituents Re~ Rd and Ak corresponds for each ~G..I~ound to a line of Table 0 Table 1249 Compounds of the general formula I.K (n = 0) in~which UR' is methoxy, VR" is ethylamino, Rf is hydrogen and the combination of 40 the substituents Re~ Rd and Ak corresponds for each com~ound to a line of Table 0 = ~ ~
2199~22 Table 1250 Compounds of the general f ormula I.R (n = 0) in which UR' is ethoxy, VR" is ethylamino, Rf is hydrogen and the combination of 5 the substituents Re~ Rd and Ak corresponds for each compo~nd to a line of Table O
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No. Re Rd Ak O
179 CH3 CH3 3~4-(OCH3) ff 6H3-cH2 ~
180 CH3 CH3 3,5-~OCH3)2-C6H3-CH2 P
181 CH3 CH3 3,4~5-(ocH3)3-c6H2-cHz 182 CH3 CH3 2-OC2Hs-C6H4-CH2 183 CH3 CH3 3-OC2Hs-C6H4-CH2 184 CH3 CH3 4-OC2Hs-C6H4-CH2 185 CH3 CH3 2-o-(n-c3H~)-c6H4-cH2 186 C~3 CH3 3-o-(n-C3H7)-C6H4-CH2 187 CH3 CH3 4-O-(n-.C3H7)-C6H4-CHz 188 CH3 CH3 2-o-(i-c3H7)-c6H4-cH2 w 189 CH3 CH3 3-o-(i-c3H7)-c6H4-cH2 w 190 CH3 CH3 4_o-(i-c3H7)-c6H4-cH2 191 CH3 CH3 4-o-(n-C4Hg)-C6H4-CH2 192 CH3 CH3 3-o-(t-c4H9)-c6H4-cH2 193 CH3 CH3 4-o-(n-C6Hl3)-C6H4-CH2 194 CH3 CH3 2-O-Allyl- 4 H4-CH2 195 CH3 CH3 3-O-Allyl-C6H4-CH2 196 CH3 CH3 4-O-Allyl-C6H4-CHz 197 CH3 CH3 2-CF3-C6H4-CH2 . ~3 198 CH3 CH3 3-CF3-C6H4-CH2 Cc~
C~
No . Re Rt Ak Vl o 199 CH3 CH3 4-cF3-c6H4-cH2 200 CH3 CH3 2-Acetyl-C6H4-CH2 ~
201 CH3 CH3 3-Acetyl-C6H4-CH2 202 CH3 CH3 4-Acetyl-C6H4-CH2 203 CH3 CH3 2-Methoxycarbonyl-c6H4-cH2 204 CH3 CH3 3-Methoxycarbonyl-C6H4-CH2 205 CH3 CH3 4-Methoxycarbonyl-C6H4-CH2 206 CH3 CH3 2-Am;noc~rbonyl-C6H4-CH2 207 CH3 CH3 3-Am;no~rbonyl-C6H4-CH2 208 CH3 CH3 4-Am;nocArbonyl-C6H4-CH
209 CH3 CH3 2-Dimethyl~~;noc~rbonyl-c6H4-cH2 210 CH3 CH3 3-Dimethylam;noc~rbonyl-C6H4-CH2 211 CH3 CH3 4-DImethylaminocarbonyl-c6H4-cH2 212 CH3 CH3 2-(N-Methylam;no~rbonyl)-C6H4-CHz 213 CH3 CH3 3-~N-Methylaminoc~rbonyl~-c6H4-cH2 214 CH3 CH3 4-(N-MethylaminocArbonyl)-c6H4-cH2 218 CH3 CH3 2-Aminothiocarbonyl-C6H4-CH
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259 CH3 CH3 2-(3'-Nitrophenoxy)eth-1-yl ~
260 CH3 CH3 2-~4'-NitrorhPnoxy)eth-1-yl O
261 CH3 CH3 2-(2'-Methoxyphenoxy)eth-1-yl 262 CH3 CH3 2-(3'-Methoxyph~no~y)eth-l-yl 263 CH3 CH3 2-(4'-Methoxyph~no~y)eth-1-yl 264 CH3 CH3 2-(2'-Trifluoromethylphenoxy)eth-1-yl265 CH3 CH3 2-(3'-Trifluoromethylphenoxy)eth-l-yl266 CH3 CH3 2-(4'-Trifluoromethylrh~noYy)eth 267 CH3 CH3 2-(2'-Acetylphenoxy)eth-1-yl 268 CH3 CH3 2-(3'-Acetyl~h~noYy)eth-l-yl w 269 CH3 CH3 2-(4'-AcetylphenQYy)eth-l-yl 270 CH3 CH3 2-(2'-Methoxycarbonyl)eth-1-yl 271 CH3 CH3 2-(3'-Methoxycarbonyl)eth-l-yl 272 CH3 CH3 2-(4'-Methoxycarbonyl)eth-l-yl 273 CH3 CH3 2-(2'-Dimethyla~;noc~rbonyl)eth-l-yl 274 CH3 CH3 2-(3~-DLmethylaminoc~rbonyl)eth 27 5 CH3 CH3 2-(4'-Dimethylam;no~Arbonyl)eth-l-yl 276 CH3 CH3 2-(2'-Aminothiocarbonyl)eth-1-yl 277 CH3 CH3 2-(3'-Aminoth; ocArbonyl )eth-l-yl 278 CH3 CH3 2-(4' ~;nothiocarbonyl)eth-1-yl c~
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No. Re R~ Ak o o 379 CH3 CH3 4-chloroth; ~701 -2-ylmethyl P
380 CH3 CH3 5-chloroth; ~701 -2-ylmethyl O
381 CH3 CH3 4-Thiazolylmethyl 382 CH3 CH3 2-Methylth;~z~1-4-ylmethyl 383 CH3 CH3 5-Methylthiazol-4-ylmethyl 384 CH3 CH3 2-chloro~h;~7ol-4-ylmethyl 385 CH3 CH3 5-chloroth~zol-4-ylmethyl 386 CH3 CH3 5-Thiazolylmethyl 387 CH3 CH3 2-Methylth; ~701 -5-ylmethyl 388 CH3 CH3 4-Methylth;~7O1-5-ylmethyl w 389 CH3 CH3 2-chloro~hi~7O1-5-ylmethyl w 390 CH3 CH3 4-chlorothiazol-5-ylmethyl 391 CH3 CH3 3-Isoxazolylmethyl 392 CH3 CH3 4-MethylisoY~zol-3-ylmethyl 393 CH3 CH3 5-Methylieoy~zol-3-ylmeth 394 CH3 CH3 4-chloroisoxazol-3-ylmethyl 395 CH3 CH3 5-chloroisoY~ol-3-ylmethyl 396 CH3 CH3 4-Isoxazolylmethyl 397 CH3 CH3 3-Methylisoxazol-4-ylmethy7 398 CH3 CH3 " 5-Methylisoxazol-4-ylmethyl C~
Cs3 No. R~ Rd Ak o ~
399 CH3 CH3 3-chloroiso~A7Ol-4-ylmethyl ~
400 CH3 CH3 5-chloroiso~701-4-ylmethyl 0 401 CH3 CH3 5-Isoxazolylmethyl 402 CH3 CH3 3-MethylisoY~ 701 -5-ylmethyl 403 CH3 CH3 4-Methyl;so~7sl-5-ylmethyl 404 CH3 CH3 3-chloroiso~7-o1-5-ylmethyl 405 CH3 CH3 4-chloroisoxazol-5-ylmethyl 406 CH3 CH3 3-I~othiazolylmethyl 407 CH3 CH3 4-Methyliso~h; A701 -3-ylmethyl 408 CH3 CH3 5-Methylisoth;~zol -3-ylmethyl 409 CH3 CH3 4-chloroisoth;~ol -3-ylmethyl 410 CH3 CH3 5-chloroiso~h;~ol -3-ylmethyl 411 CH3 CH3 4-Isoth;~701 ylmethyl 412 CH3 CH3 3-Methylisothiazol-4-ylmethyl 4l3 CH3 CH3 . 5-Methylisothi~70l-4-ylmethyl 414 CH3 CH3 3-chloroisothiazol-4-ylmethyl 415 CH3 CH3 5-chloroiso~h;~zol-4-ylmethyl 416 CH3 CH3 5-Isothiazolylmethyl 417 CH3 CH3 3-Methylisothi~701-5-ylmethyl 41B CH3 CH3 4-Methylisothiazol-5-ylmethyl ~~~
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742 CH3 4-Thiazolyl CH3 743 CH3 4-Thiazolyl C2H5 744 CH3 4-Th; ~701 yl n-C3H7 745 CH3 4-Thiazolyl i-c3H7 746 CH3 3-Isoxazolyl H
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752 CH3 5-Isoxazolyl CH3 753 CH3 5_ISOYA701Y1 C2H5 754 CH3 5-TsoY~z~lyl n-C3H7 755 CH3 5-Isoxazolyl i-c3H7 7S6 CH3 2-Imidazolyl H
757 CH3 2-Imidazolyl CH
758 CH3 2-Imidazolyl C2H
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882 OCH3 3_ISOYA70~Y1 CH3 883 OCH3 3-Isoxazolyl C2H5 884 OCH3 3_ISOX~7Q1Y1 n-C3H7 1 885 OCH3 3_ISOYA701Y1 i-C3H7 886 OCH3 5-Isoxazolyl H
887 OCH3 5_ISOXA701Y1 CH3 888 OCH3 5_ISOXA~O1Y1 C2Hs P
889 OCH3 5-Isoxazolyl n-C3H7 890 OCH3 5_ISOYA701Y1 i-C3H7 891 OCH3 2 - T ; ~A701 yl H
892 OCH3 2-Imidazolyl CH3 893 OCH3 2-Imidazolyl C2H5 894 OCH3 2-Imidazolyl n-C3H7 895 OCH3 2-Imidazolyl i-C3H7 896 OCH3 3-Pyrazolyl ~ H
897 OCH3 3-Pyrazolyl CH
898 OCH3 3-Pyrazolyl CzH5 CS~
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1000 OH 2-OY~ZO1Y1 i-C3H7 ~
1001 OH 4-Oxazolyl H
1002 OH 4-Oxazolyl CH3 1003 OH 4-OY~ZO1Y1 C2H5 1004 OH 4-Oxazolyl n-C3H7 1005 OH 2-Thiazolyl i-c3H7 1006 OH 2-Thiazolyl H
1007 OH 2-Thiazolyl CH3 1008 OH 2-Thiazolyl C2H
1009 OH 2-Thiazolyl n-C3H7 1010 OH 2-Thiazolyl i-C3H7 1011 OH 4-Thiazolyl H ~!
1012 OH 4-Thiazolyl CH3 1013 OH 4-Th;~7~1yl C2H5 1014 OH 4-IsoY~zolyl n-C3H7 1015 OH 4-Isoxazolyl i-c3H7 1016 OH 3-Isoxazolyl H
1017 OH ' 3-Isn~zolyl CH
1018 OH 3-Iso~zo~yl C2H5 ~-~
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1019 OH 3-Isoxazolyl n-C3H7 ~
1020 OH 3-Isoxazolyl i-C3H7 ~
1021 OH 5-Isoxazolyl H
1022 OH 5-Isoxazolyl CH3 1023 OH 5_I~OY~7O1Y1 C2Hs 1024 OH 5-Isox~zolyl n-C3H7 1025 OH 5-Isoxazolyl i-C3H7 1026 OH 2-Imidazolyl H
1027 OH 2-Imidazolyl CH3 1028 OH 2-Imidazolyl C2H
1029 OH 2-Imidazolyl n-C3H7 1030 OH 2-Imidazolyl i-C3H7 1031 OH 3-Pyrazolyl H
1032 OH 3-Pyrazolyl CH3 1033 OH 3-Pyrazolyl C2H5 1034 OH 3-Pyrazolyl n-C3H7 1035 OH 3-Pyrazolyl i-C3H7 1036 OH 4-Pyrazolyl H
1037 OH 4-Pyrazolyl CH3 1033 OH 4-Pyrazolyl C2H
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1120 SCH3 SCH3 i-C3H7 1121 SC83 Cyclop.~pyl H
1122 SCH3 Cyclopropyl CH3 1123 SCH3 Cyclopropyl C2H5 1124 SCH3 Cyclopropyl n-C3H7 1125 SC83 CYC1~L~PY1 i-c3H7 1126 Cyclopropyl H H
1127 Cyclopropyl H CH3 1128 Cyclopropyl H C2H5 p 1129 Cyclopropyl H n-C3H7 1130 Cyclopropyl H i-c3H7 1131 Cyclopropyl OH
1132 Cyclopropyl OH CH3 1133 Cyclop~o~yl OH C2H5 1134 Cyclopropyl OH n-C3H7 1135 Cyclopropyl OH i-C3H7 1136 Cyclopropyl Cl n-C4Hg 1137 Cyclopropyl Cl CH3 1138 Cyclopropyl Cl C2H5 ~_~
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o No. Re Rd A~ o o 1179 CH3 3-F-C6H4 3-Methyl-but-2-en-1-yl ~
1180 CH3 4-F-C6H4 H ~
1183 CH3 4-F-C6H4 n-C3H7 1184 CH3 4-F-C6H4 i-C3H7 1185 CH3 4-F-C6H4 n-C4Hg 1186 CH3 4-F-C6H4 t-C4Hg 1187 CH3 4-F-C6H4 n-C6H13 1188 CH3 4-F-C6H4 Prop-1-en-3-yl ~
118g CH3 4-F-C6H4 (E)-1-chloLu~op-l-en-3-yl w 1190 CH3 4-F-C6H4 Propyn-3-yl 1191 CH3 4-F-C6H4 3-Methyl-~ut-2-en-1-yl 1192 CH3 2-Cl-C6H4 H
1193 CH3 2-Cl-C6H4 CH3 1194 CH3 2-Cl-C6H4 C2H5 1195 CH3 2-Cl-C6H4 n-C3H7 1196 CH3 2-Cl-C6H4 i-C3H7 1197 CH3 2-Cl-C6H4 n-C4H
1198 CH3 2-cl-C6H4 t-C4Hg C~
Cs~
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f ~ -No. R Rd Ak o 1199 CH3 2-Cl-C6H4 n-C6Hl3 1200 CH3 2-Cl-C6H4 Prop-l-en-3-yl 1201 CH3 2-Cl-C6H4 ~E)-l-ChloLo~Lo~-l-en-3-yl N
1202 CH3 2-Cl-C6H4 Propyn-3-yl 1203 CH3 2-Cl-C6H4 3-Methyl-but-2-en-1-yl 1204 CH3 3-Cl-C6H4 H
1205 CH3 3-Cl-C6H4 CH3 1206 CH3 3-Cl-C6H4 C2H5 1207 CH3 3-Cl-C6H4 n-C3H7 1208 CH3 3-Cl-C6H4 i-C3H7 120g CH3 3-Cl-C6H4 n-C4H
1210 CH3 3-Cl-C6H4 t-C4Hg 1211 CH3 3-Cl-C6Hg n-C6Hl3 1212 CH3 3-Cl-C6H4 Prop-l-en-3-yl 1213 CH3 3-Cl-C6H4 (E)-l-Chloroprop-l-en-3-yl 1214 CH3 3-Cl-C6H4 ~Gp~.l-3-yl 1215 CH3 3-Cl-C6H4 3-Methyl-but-2-en-1-yl 1216 CH3 4-Cl-C6H4 H
1217 CH3 4-Cl-C6H4 CH3 1218 CH3 4-Cl-C6H4 C2Hs 1219 C~3 4-Cl-C6H~ n-C3H
No. R Rd Ak o 1220 CH3 4-Cl-C6H4 i-C3H7 w 1221 CH3 4-Cl-C6H4 n-C4Hg ~
1222 CH3 4-Cl-C6H4 t-C4Hg O
1223 CH3 4-Cl-C6H4 n-C6H13 1224 CH3 4-Cl-C6H4 Prop-1-en-3-yl 1225 CH3 4-Cl-C6H4 (E)-1-Chloroprop-1-en-3-yl 1226 CH3 4-Cl-C6H4 ~opy~-3-yl 1227 CH3 4-Cl-C6H4 3-Methyl-but-2-en-1-yl 1228 CH3 2,3-Cl2-C6H3 H
1229 CH3 2,3-Cl2-C6H3 CH3 1230 CH3 2,3-Cl2-C6H3 C2H
1231 CH3 2,3-Cl2-C6H3 n-C3H~
1232 CH3 2,3-Clz-C6H3 i-c3H7 1233 CH3 2,3-Cl2-C6H3 n-C4Hg 1234 CH3 2,3-Cl2-C6H3 t-C4Hg 1235 CH3 2,3-Cl2-C6H3 - n-C6Hl3 1236 CH3 2,3-Cl2-C6H3 Prop-1-en-3-yl 1237 CH3 2,3-C12-C6H3 (E)-1-Chloroprop-1-en-3-yl 1238 CH3 2,3-C12-C6H3 ~ yl,-3-yl 1239 CH3 2,3-C12-C6H3 3-Methyl-but-2-en-1-yl 1240 CH3 2,4-C12-C6H3 H
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~ !-No. R Rd Ak o 1283 CH3 3,4-C12-C6H3 n-CcHl3 1284 CH3 3,4-Cl2-C6H3 Prop-l-en-3-yl p 1285 CH3 3,4-Cl2-C6H3 (E)-1-Chloroprop-l-en-3-yl O
1286 CH3 3,4-C12-C6H3 . ~Lo~yl~-3-yl 1287 CH3 3,4-C12-C6H3 3-Methyl-but-2-en-1-yl 1288 CH3 3,5-C12-C6H3 H
1289 CH3 3,5-C12-C6H3 CH3 1290 CH3 3,5-Cl2-C6H3 CzH5 1291 CH3 3,5-Cl2-C6H3 n-C3H7 1292 CH3 3,5-C12-C6H3 i-C3H7 i293 CH3 3~5-C12-C6H3 n-C4Hg N
1294 CH3 3,5-Cl2-C6H3 t-C4Hg 1295 CH3 3,5-Cl2-C6H3 n-C6Hl3 1296 CH3 3,5-Cl2-C6H3 Prop-l-en-3-yl 1297 CH3 3,5-C12-C6H3 (E)-l-Chloroprop-l-en-3-yl -1298 CH3 3,5-Cl2-C6H3 Propyn-3-yl 1299 CH3 3,5-C12-C6H3 3-Methyl-~ut-2-en-1-yl 1300 CH3 2-Br-C6H4 H
1301 C~3 2-Br-C6H4 CH3 1302 CH3 2-Br-C6H4 C2H5 1303 CH3 2-Br-C6H4 n-C3H7 C~
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~ No. R Rd Ak o 1410 CH3 2-NO ff 6H4 C2H5 . p 1411 CH3 2-NO2-C6H4 n-C3H7 o 1412 CH3 2-NO2-C6H4 i-C3H7 1413 CH3 2-NO2-C6H4 n-C4Hg 1414 CH3 2-NO2-C6H~ t-C4H9 1415 CH3 2-NO2-C6H4 n-C6Hl3 1416 CH3 2-NO2-C6H4 Prop-l-en-3-yl - 1417 CH3 2-NO2-C6H4 ~E)-l-ChloLoy~oy-l-en-3 1418 CH3 2-NO2-C6H4 Propyn-3-yl 1419 CH3 2-NO2-C6H4 3-Methyl-but-2-en-1-yl w 1423 CH3 3-NO2-C6H4 n-C3H7 1424 CH3 3-NO2-C6H4 i-c3H7 1425 CH3 3-NO2-C6H4 n-C4Hg 1426 CH3 3-NOz-C6H4 t-C4Hg 1427 CH3 3-NO2-C6H4 n-C6H13 1428 CH3 3-NO2-C6H4 Prop-l-en-3-yl .
1429 CH3 3-N02-C6H4 (E)-l-Chloroprop-l-en-3-yl C~
il~ 0050/45204 2199~22 ,i , _I
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No. R Rd Ak o 1451 CH3 2-CH3-C6H4 n-C6Hl3 1452 CH3 2-CH3-C6H4 Prop-1-en-3-yl ~
1453 CH3 2-CH3-C6H4 (E)-1-Chloroprop-1-en-3-yl O
1454 CH3 2-CH3-C6H4 Propyn-3-yl 1455 CH3 2-CH3-C6H4 3-Methyl-but-2-en-1-yl 1459 CH3 3-CH3-C6H4 n-C3H~
1460 CH3 3-CH3-C6H4 i-C3H7 1461 CH3 3-CH3-C6H4 n-C4Hg w 1462 CH3 3-CH ff 6H4 t-C4Hg 1463 CH3 3-CH3-C6H4 n-C6H13 1464 CH3 3-CH3-C6H4 Prop-1-en-3-yl 1465 CH3 3-CH3-C6H4 (E)-l-Chloroprop-1-en-3-yl 1466 CH3 3-CH3-C6H4 Propyn-3-yl 1467 CH3 3-CH3-C6H4 3-Methyl-but-2-en-1-yl 1471 CH3 4-CH3-C6H4 n-C3H7 ~_~
CD
No. R Rd Ak o 1472 CH3 4-CH3-C6H4 i-C3H7 o 1473 CH3 4-CH3-C6H4 n-C4H
1474 CH3 4-CH3-C6H4 t-C4Hg O
1475 CH3 4-CH3-C6H4 n-C6Hl3 1476 CH3 4-CH3-C6H4 Prop-l-en-3-yl 1477 CH3 4-CH3-C6H4 (E)-l-ChloLo~Lo~-1-en-3-yl 1478 CH3 4-CH3-C6H4 ~-o~yl.-3-yl 1479 CH3 4-CH3-C6H4 3-Methyl-but-2-en-1-yl 1480 CH3 2,3-(CH3)z-C6H3 H
1481 CH3 2,3-(CH3)2-C6H3 CH3 1482 CH3 2,3-(CH3)2-C6H3 C2H
1483 CH3 2,3-(CH3)2-C6H3 n-C3H7 1484 CH3 2,3-(CH3)2-C6H3 i-c3H7 1485 CH3 2,3-(CH3)2-C6H3 n-C4Hg 1486 CH3 2,3-(CH3)2-C6H3 t-C4Hg 1487 CH3 2,3-(CH3)2-C6H3 n-C6Hl3 1488 CH3 2,3-(CH3)2-C6H3 Prop-l-en-3-yl 1489 CH3 2,3-(CH3)2-C6H3 (E)-l-ChloLopLu~-l-en-3-yl 1490 CH3 2,3-(CH3)2-C6H3 Propyn-3-yl 1491 CH3 2,3-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl ~3 1492 CH3 2,4-(CH3~2-C6H3 H ~_~
No. R Rd A~ g 1493 CH3 2,4-(CH3) ff 6H3 CH
1494 CH3 2,4-(CH3)2-C6H3 C2Hs 1495 CH3 2,4-(CH3) ff 6H3 n-C3H7 o 1496 CH3 2,4-(CH3)2-C6H3 i-C3H7 1497 CH3 2,4-(CH3)2-C6H3 n-C4H
1498 CH3 2,4-~CH3)2-C6H3 t-C4Hg 1499 CH3 2,4-(CH3)2-C6H3 n-C6H13 1500 CH3 2,4-(CH3)2-C6H3 Prop-1-en-3-yl 1501 CH3 2,4-(CH3)2-C6H3 (E)-1-Chloroprop-1-en-3-yl 1502 CH3 2,4-~CH3)2-C6H3 Propyn-3-yl lS03 CH3 2,4-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl w 1504 CH3 2,5-(CH3)2-C6H3 H
1505 CH3 2,5-(CH3)2-C6H3 CH3 1506 CH3 2,5-(CH3)2-C6H3 C2H5 1507 CH3 2,5-(CH3)2-C6H3 n-C3H7 1508 CH3 2,5-(CH3)2-C6H3 i-C3H7 lS09 CH3 2,5-(CH3)2-C6H3 n-C4Hg 1510 CH3 2,5-(CH3) ff 6H3 t-C4Hg 1511 CH3 2,5-(CH3)2-C6H3 n-C6Hl3 1512 CH3 2,5-(CH3)2-C6H3 Prop-1-en-3-yl 1513 CH3 2,5-(CH3)2-C6H3 (E)-1-Chloroprop-1-en-3-yl C~
No. R Rd A~ g lS14 CH3 2,5-(CH3)2-C6H3 Propyn-3-yl 0 1515 CH3 2,5-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl ~
i516 CH3 2,6-(CH3)2-C6H3 H o i517 CH3 - 2,6-(CH3)2-C6H3 CH3 1518 CH3 2,6-(CH3)2-C6H3 C2Hs 1519 CH3 2,6-(CH3)2-C6H3 n-C3H7 1520 CH3. 2,6-(CH3)2-C6H3 i-C3H7 1521 CH3 2,6-(CH3)2-C6H3 n-C4H9 1522 CH3 2,6-(CH3)2-C6H3 t-C4Hg 1523 CH3 2,6-(CH3)2-C6H3 n-C6H13 1524 CH3 2,6-(CH3)2-C6H3 Prop-1-en-3-yl w 1525 CH3 2,6-(CH3)2-C6H3 (E)-l-Chloroprop-1-en-3-yl 1526 CH3 2,6-(CH3)2-C6H3 Propyn-3-yl 1527 CH3 2,6-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl 1528 CH3 3,4-(CH3)2-C6H3 H
1529 CH3 3~4-(cH3)2-c6H3 CH3 1530 CH3 3,4_(CH3)2-C6H3 C2H5 1531 CH3 3,4-(CH3)2-C6H3 n-C3H7 1532 CH3 3,4-(CH3)2-C6H3 i-C3H7 1533 CH3 3~4-(cH3)2-c6H3 n-C4H
1534 CH3 3,4-(CH3)2-C6H3 t-C4Hg C~
, f ~ ~
No. R Rd Ak o 1535 CH3 3,4-(C83)2-C6H3 n-C6Hl3 1536 CH3 3,4-(CH3) ff 6H3 ~rop-1-en-3-yl . ~
1537 CH3 3,4-(CH3)2-4H3 (E)-1-Chlo~o~G~ en-3-yl O
1538 CH3 3,4_~CH3)2-C6H3 Propyn-3-yl 1539 CH3 3,4-(CH3)2-C6H3 3-Methyl-but-2-en-1-yl 1540 CH3 3,5-(CH3)2-C6H3 H
1541 CH3 3,5-(CH3)2-C6H3 CH3 1542 CH3 3,5-(CH3)2-C6H3 C2H5 1543 CH3 3,5-(CH3)2-C6H3 n-C3H7 1544 CH3 3,5-(CH3)2-C6H3 i-C3H7 1545 CH3 3,5-(CH3)2-C6H3 n-C4H
1546 CH3 3,5-(CH3)2-C6H3 t-C4Hg 1547 CH3 3,5-(CH3)2-C6H3 n-C6H13 1548 CH3 3,5-(CH3)2-C6H3 Prop-l-en-3-yl 1549 CH3 3,5-(CH3)z-C6H3 (E)-1-Chlolo~o~-1-en-3-yl 1550 CH3 3,5-(CH3)2-C6H3 Propyn-3-yl 1551 CH3 3,5-(CH3) ff 6H3 3-Methyl-but-2-en-1-yl 1552 CH3 2-C2Hs-C6H4 H
1553 CH3 2-C2Hs-C6H4 CH3 1554 CH3 2-C2H5-C6H~ C2H5 1555 CH3 2-C2Hs-C6H4 n-C3H7 f ~ ~ ~, ,.
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No. R Rd Ak o 1577 CH3 4-CzHs-C6H4 CH
1578 CH3 4-C2Hs-C6H4 C2Hs 1579 CH3 4-C2Hs-C6H4 n-C3H7 N
1580 CH3 4-C2Hs-C6H4 i-C3H7 1581 CH3 4-C2Hs-C6H4 n-C4Hg 1582 CH3 4-C2Hs-C6H4 t-C4Hg 1583 CH3 4-C2Hs-C6H4 n-C6H13 1584 CH3 4-C2Hs-C6H4 Prop-l-en-3-yl 1585 CH3 4-C2H5-C6H4 (E)-l-ChluLo~Lup-l-en-3-yl 1586 CH3 4-C2Hs-C6H4 Propyn-3-yl 1587 CH3 4-C2Hs-C6H4 3-Methyl-but-2-en-1-yl 1588 CH3 2-i-C3H7-C6H4 H
1589 CH3 2-i-C3H7-C6H4 CH3 1590 CH3 2-i-C3H7-C6H4 C2H5 1591 CH3 2-i-C3H7-C6H4 n-C3H7 1592 CH3 2-i-C3H7-C6H4 i-C3H7 1593 CH3 2-i-c3H7-c6H4 n-C4Hg 1594 CH3 2-i-C3H7-C6H4 t-C4Hg 1595 CH3 2-i-C3H7-C6H4 n-C6H13 1596 CH3 2-i-c3H7-c6H4 Prop-l-en-3-yl r~
1597 CH3 2-i-C3H7-C6H4 (E)-l-ChloLo~Lo~-l-en-3-yl CS~
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No. R Rd Ak o 1619 CH3 4-i-C3H7-C6H4 n-C6H13 ~
1620 CH3 4-i-C3H7-C6H4 Prop-l-en-3-yl 1621 C~3 4-i-C3H7-C6H4 (E)-1-Chloroprop-l-en-3-yl 1622 CH3 4-i-C3H7-C6H4 Propyn-3-yl 1623 CH3 4-i-C3H7-C6H4 3-~ethyl-but-2-en-1-yl 1626 CH3 2-OH-C6H4 C2Hs 1627 CH3 2-OH-C6H4 n-C3H7 1628 CH3 2-OH-C6H4 i-C3H7 1629 CH3 2-OH-C6H4 n-C4Hg 163Q CH3 2-OH-4H4 t-C4Hg 1631 CH3 2-oH-c6H4 n-C6Hl3 1632 CH3 2-OH-C6H4 Prop-1-en-3-yl 1633 CH3 2-OH-C6H4 (E)-1-Chloroprop-1-en-3-yl 1634 CH3 2-OH-C6H4 Propyn-3-yl 1635 CH3 2-OH-C6H4 3-Methyl-but-2-en-1-yl 1638 CH3 3-OH-C6H4 C2Hs 1639 CH3 3-OH-C6H4 n-C3H7 4 f~
No. R Rd Ak g 1640 CH3 3-OH-C6H4 i-C3H7 o 1641 CH3 3-OH-C6H4 n-C4H9 w 1642 CH3 3-OH-C6H4 t-C4Hg O
1643 CH3 3-OH-C6H4 n-C6H13 1644 CH3 3-OH-C6H4 Prop-1-en-3-yl 1645 CH3 3-OH-C6H4 (E)-1-Chloroprop-1-en-3-yl 1646 CH3~ 3-OH-C6H4 Propyn-3-yl 1647 CH3 3-OH-C6H4 3-Methyl-but-2-en-1-yl 1651 CH3 4-OH-C6H4 n-C3H7 1652 CH3 4-OH-C6H4 i-C3H7 1653 CH3 4-OH-C6H4 n-C4H9 1654 CH3 4-OH-4H4 t-C4Hg 16SS CH3 4-OH-C6H4 n-C6H13 16S6 CH3 4-OH-C6H4 Prop-1-en-3-yl 1657 CH3 4-OH-C6H4 (E)-1-Chlolo~o~-1-en-3-yl 1658 CH3 4-OH-C6H4 Propyn-3-yl 1659 CH3 4-OH-C6H4 3-Methyl-but-2-en-1-yl ~~~
f~ - ~
--No. R Rd Ak o 1662 CH3 2-OCH3-C6H4 C2Hs . ~
1663 CH3 2-OCH3-C6H4 n-C3H7 O
1664 CH3 2-OCH3-C6H4 i-C3H7 1665 CH3 2-OCH3-C6H4 n-C4Hg 1666 CH3 2-OCH3-C6H4 t-C4Hg 1667 CH3 2-OCH3-C6H4 n-C6Hl3 1668 CH3 2-OCH3-C6H4 Prop-1-en-3-yl 1669 CH3 2-OCH3-C6H4 (E)-1-Chloroprop-l-en-3-yl 1670 CH3 2-OCH3-C6H4 Propyn-3-yl 1671 CH3 2-OCH3-C6H4 3-Methyl-but-2-en-1-yl 1672 CH3 3-OCH3-c6H4 H
1673 CH3 3_oCH3-C6H4 CH3 1674 CH3 3_OCH3-C6H4 C2H5 1675 CH3 3_OCH3-C6H4 n-C3H7 1676 CH3 3-OCH ff 6H4 i-C3H7 1677 CH3 3-OCH3-C6H4 n-C4Hg 1678 CH3 3_OCB ff 6H4 t-C4Hg 1679 CH3 3-OCH3-C6H4 n-C6Hl3 1680 CH3 3-OCH3-C6H4 Prop-1-en-3-yl 1681 CH3 3_oCH3-C6H4 tE)-1-Chloroprop-l-en-3 ~ 0050/45204 2~99~22 ,, ' ,, a) ~' i ,.~ ~ -.~ ~ o J~ ru7 U U ~ U U ~ ~ ~ ~ 5 U U ~ 1-5~ m ~ 5~ r C~ 5 5r ,~ ~ 5~ m L sr r m ~ m _, ~ m O O 0 0 o o ~ ~ O O O U
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m m m m :~ r m mU Ux :': mu mu m m IU o U U U u u No. R Rd Ak o 1850 CH3 2-NH2-C6H4 Pxopyn-3-yl O
1851 CH3 2-NH2-C6H4 3-Methyl-but-2-en-l-yl 1852 CH3 3-NH2-C6H4 H o 1853 CH3 3-NH ff 6H4 CH3 1855 CH3 3-NH2-C6H4 n-C3H7 1856 CH3 3-NH2-C6H4 i-C3H7 1857 CH3 3-NH2-C6H4 n-C4Hg 1858 CH3 3-NH2-C6H4 t-C4Hg 1859 CH3 3-NH2-C6H4 n-C6HI3 1860 CH3 3-NH2-C6H4 Prop-l-en-3-yl P
1861 CH3 3-NH2-C6H4 ~E)-l-Chloroprop-l-en-3-yl 1862 CH3 3-NH2-C6H4 Propyn-3-yl 1863 CH3 3-NH2-C6H4 3-Methyl-but-2-en-1-yl 1867 CH3 4-NH ff 6H4 n-C3H7 1868 CH3 4-NH ff 6H4 i-C3H7 1869 CH3 4-NH2-C6H4 n-C4Hg 1870 CH3 4-NH2-C6H4 t-C4Hg C~
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~o~o.o.oooooooooooooooooo No. R Rd Ak o 2018 CH3 4-SCH ff 6H4 Propyn-3-yl 2019 CH3 4-SCH3-C6H4 3-Methyl-but-2-en-1-yl ~
2020 CH3 2-Methylsulfonyl-C6H4 H o 2021 CH3 2-Methylsulfonyl-C6H4 CH3 2022 C~3 2-Methylsulfonyl-C6H4 C2H5 2023 CH3 2-Methylsulfonyl-C6H4 n-C3H7 2024 CH3 2-Methylsulfonyl-C6H4 i-C3H7 2025 C~3 2-Methylsulfonyl-C6H4 n-C4H9 2026 CH3 2-Methylsulfonyl-C6H4 t-C4Hg 2027 CH3 2-Methylsulfonyl-C6H4 n-C6H13 2028 CH3 2-Methylsulfonyl-C6H4 Prop-1-en-3-yl ~
2029 CH3 2-Methylsulfonyl-C6H4 (E)-l-Chloroprop-1-en-3-yl w 2030 CH3 2-Methylsulfonyl-C6H4 Propyn-3-yl 2031 CH3 2-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2032 CH3 3-Methylsulfonyl-C6H4 H
2033 CH3 3-Methylsulfonyl-C6H4 CH3 2034 CH3 3-Hethylsulfonyl-C6H4 C2H5 2035 CH3 3-Methylsulfonyl-C6H4 n-C3H7 2036 CH3 3-Methylsulfonyl-C6H4 i-C3H
2037 C~3 3-Methylsulfonyl-C6H4 n-C4H
2038 CH3 3-Methylsulfonyl-C6H4 t-C4H
No. R Rd Ak o 2039 CH3 3-Methylsulfonyl-C6H4 n-C6Hl3 2040 CH3 3-Methylsulfonyl-C6H4 Prop-1-en-3-yl ~
2041 CH3 3-Methylsulfonyl-C6H4 (E)-l-Chloroprop-l-en-3-yl O
2042 CH3 3-Methylsulfonyl-C6H4 Propyn-3-yl 2043 CH3 3-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2044 CH3 4-Methylsulfonyl-C6H4 H
2045 CH3 4-Methylsulfonyl-C6H4 CH3 2046 CH3 4-Methylsulfonyl-C6H4 C2H5 2047 CH3 4-Methylsulfonyl-C6H4 n-C3H7 2048 CH3 4-Methylsulfonyl-C6H4 i-c3H
2049 CH3 4-Methylsulfonyl-C6H4 n-C4Hg 2050 CH3 4-Methylsulfonyl-C6H4 t-C4Hg 2051 CH3 4-Methylsulfonyl-C6H4 n-C6H13 2052 CH3 4-Methylsulfonyl-C6H4 Prop-l-en-3-yl 2053 CH3 4-Methylsulfonyl-C6H4 (B)-1-Chloroprop-l-en-3-yl 2054 CH3 4-Methylsulfonyl-C6H4 Propyn-3-yl 2055 CH3 4-Methylsulfonyl-C6H4 3-Methyl-but-2-en-1-yl 2056 CH3 2-Methoxyc~rbo~yl-C6H4 H
2057 CH3 2-Methoxycarbonyl-C6H4 CH
2058 CH3 2-Methoxycarbonyl-C6H4 C2H5 . ~_~
2059 CH3 2-Methoxycarbonyl-C6H4 n-C3H7 CC~
No. R Rd Ak o 2060 CH3 2-Methoxycarbonyl-C6H4 i-c3H7 2061 CH3 2-Methoxycarbonyl-C6H4 n-C4Hg 2062 CH3 2-Methoxycarbonyl-C6H4 t-C4Hg 2063 CH3 2-Methoxycarbonyl-C6H4 n-C6H13 2064 CH3 2-Methoxycarbonyl-C6H4 Prop-l-en-3-yl 2065 CH3 2-Methoxycarbonyl-C6H4 (E)-1-Chloroproe-l-en-3-yl 2066 CH3 2-Methoxycarbonyl-C6H4 Propyn-3-yl 2067 CH3 2-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2068 CH3 3-Methoxycarbonyl-C6H4 H
2069 CH3 3-Methoxycarbonyl-C6H4 CH3 2070 CH3 3-Methoxycarbonyl-C6H4 C2H
2071 CH3 3-Methoxycarbonyl-C6H4 n-C3H7 2072 CH3 3-Methoxycarbonyl-C6H4 i-c3H7 2073 CH3 3-Methoxycarbonyl-C6H4 n-C4Hg 2074 CH3 3-Methoxycarbonyl-C6H4 t-C4Hg 2075 CH3 3-Methoxycarbonyl-C6H4 n-C6H13 2076 CH3 3-Methoxycarbonyl-C6H4 Prop-1-en-3-yl 2077 CH3 3-Methoxycar~onyl-C6H4 (E)-1-Chloroprop-1-en-3-yl 2078 CH3 3-Methoxycar~onyl-C6H4 ~v~y~-3-y 2079 CH3 3-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2080 CH3 4-Methoxycarbonyl-C6H4 H
C~
No. R Rd Ak o 2081 CH3 4-Methoxycarbonyl-C6H4 CH
2082 CH3 4-Methoxycarbonyl-C6H4 C2H
2083 CH3 4-Methoxycarbonyl-C6H4 n-C3H7 O
2084 CH3 4-Methoxycarbonyl-C6H4 i-C3H7 2085 CH3 4-Methoxycarbonyl-C6H4 n-C4Hg 2086 CH3 4-Methoxycarbonyl-C6H4 t-C4Hg 2087 CH3 4-Methoxycarbonyl-C6H4 n-C6H13 2088 CH3 4-Methoxycarbonyl-C6H4 Prop-l-en-3-yl 2089 CH3 4-Methoxycarbonyl-C6H4 ~E)-1-Chlo~ o~-1-en-3-yl 2090 CH3 4-Methoxycarbonyl-C6H4 Propyn-3-yl 2091 CH3 4-Methoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2092 CH3 2-Bthoxycarbonyl-C6H4 H
2093 CH3 2-Ethoxycarbonyl-C6H4 CH3 2094 CH3 2-Ethoxycarbonyl-C6H4 C2H5 20g5 CH3 2-Ethoxycarbonyl-C6H4 n-C3H7 2096 CH3 2-Ethoxycarbonyl-C6H4 i-C3H7 2097 CH3 2-Ethoxycarbonyl-C6H4 n-C~Hg 2098 CH3 2-Ethoxycarbonyl-4 H4 t-C~Hg 2099 CH3 2-Ethoxycarbonyl-C6H4 n-C6H13 2100 CH3 2-Ethoxycarbonyl-C6H4 Prop-l-en-3-yl 2101 CH3 2-Ethoxycarbonyl-C6H4 (E)-1-Chloroprop-l-en-3-yl ~~~
C~
~3 No. R Rd Ak ~
2102 CH3 2-Ethoxycarbonyl-C6H4 Propyn-3-yl O
2103 CH3 2-Ethoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2104 CH3 3-Ethoxycarbonyl-C6H4 H o 2105 CH3 3-Ethoxycarbonyl-C6H4 CH3 2106 CH3 3-Ethoxycarbonyl-C6H4 CzH5 2107 CH3 3-Ethoxycarbonyl-C6H4 n-C3H7 2108 CH3- 3-Ethoxycarbonyl-C6H4 i-C3H7 2109 CH3 3-Ethoxycarbonyl-C6H4 n-C4Hg 2110 CH3 3-Ethoxycarbonyl-C6H4 t-C4Hg 2111 CH3 3-Ethoxycarbonyl-C6H4 n-C6H13 2112 CH3 3-Ethoxycarbonyl-C6H4 Prop-1-en-3-yl 2113 CH3 3-Ethoxycarbonyl-C6H4 ~E)-1-ChloLo~Lo~-1-en-3-yl 2114 CH3 3-Ethoxycarbonyl-C6H4 ~ u~y~l-3-yl 2115 CH3 3-Ethoxycarbonyl-C6H4 3-Methyl-but-2-en-1-yl 2116 CH3 4-Ethoxycarbonyl-C6H4 H
2117 CH3 4-Ethoxycarbonyl-C6H4 CH3 2118 CH3 4-Ethoxycarbonyl-C6H4 C2H
2119 CH3 4-Ethoxycarbonyl-C6H4 n-C3H7 2120 CH3 4-Ethoxycarbonyl-C6H4 i-C3H7 2121 CH3 4-Ethoxyc~rhonyl-C6H4 n-C4Hg 2 2122 CH3 4-Ethoxycarbonyl-C6H4 t-C4Hg Cc~
t~
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No. R Rd Ak g 2144 CH3 3-Aminocarbonyl-C6H4 i-C3H7 O
2145 CH3 3-Aminocarbonyl-C6H4 n-C4Hg p 2146 CH3 3-Am;noc~rbonyl-C6H4 t-C4Hg O
2147 CH3 3-Aminoc~rbonyl-C6H4 n-C6H13 2148 CH3 3-Aminocarbonyl-C6H4 Prop-l-en-3-yl 2149 CH3 3-pminoc~rbonyl-c6H4 (E)-1-Chloroprop-l-en-3-yl 2150 CH3 3-Am;noc~rbonyl-c6H4 Propyn-3-yl 2151 CH3 3-Aminocarbonyl-C6H4 3-Methyl-~ut-2-en-1-yl 2152 CH3 4-Aminoc~rbonyl-C6H4 H
2153 CH3 4-Aminoc~rbonyl-c6H4 CH3 2154 CH3 4-Aminocarbonyl-C6H4 C2H
2155 CH3 4-Aminocarbonyl-C6H4 n-C3H7 2156 CH3 4-Am;nocArbonyl-C6H4 i-C3H7 2157 CH3 4-Aminocarbonyl-C6H4 n-C4Hg 2158 CH3 4-Aminocarbonyl-C6H4 t-C4Hg 2159 CH3 4_Aminoc~rbonyl-C6H4 n-C6H13 2160 CH3 4-Aminocarbonyl-C6H4 Prop-l-en-3-yl 2161 CH3 4-Aminocarbonyl-C6H4 ~E)-1-Chloroprop-1-en-3-yl 2162 CH3 4-Am;noc~rbonyl-C6H4 Propyn-3-yl 2 2163 CH3 4-Aminoc~rbonyl-c6H4 3-Methyl-but-2-en-1-yl Cs~
2164 CH3 2-(N-Methylaminoc~rbonyl)-c6H4 H C~
f 1 ~
No. R Rd Ak o 2165 CH3 2-(N-Methylaminocarbonyl)-C6H4 CH3 O
2166 CH3 2-(N-Methylaminocarbonyl)-C6H4 C2H
2167 CH3 2-(N-Methylaminocarbonyl)-C6H4 n-C3H7 O
2168 CH3 2-(N-Methylaminocarbonyl)-C6H4 i-C3H7 2169 CH3 2-(N-Methylam; noc~ rbonyl)-C6H4 n-C4Hg 2170 CH3 2-(N-Methylam;noc~rbonyl)-C6H4 t-C4Hg 2171 CH3 2-(N-Methylaminocarbonyl)-C6H4 n-C6H13 2172 CH3 2-(N-Methylam; noC~ rbonyl)-C6H4 Prop-1-en-3-yl 2173 CH3 2-(N-Methylaminocarbonyl)-C6~4 (E)-l-Chloroprop-1-en-3-yl 2174 CH3 2-(N-Methylaminocarbonyl)-C6H4 ~L u~ -3-yl 2175 CH3 2-(N-Methy1~;noc~rbonyl)-C6H4 3-Methyl-but-2-en-1-yl 2176 CH3 3-(N-Methylam;noc~rbonyl)-c6H4 H
2177 CH3 3-(N-Methylaminocarbonyl)-C6H4 CH3 2178 CH3 3-(N-Methylami noc~rbonyl ) -C6H4 C2H5 2179 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 n-C3H7 2180 CH3 3-(N-Methylaminoc~rbonyl)-C6H4 i-C3H7 2181 CH3 3-(N-Methylaminoc~rbonyl)-c6H4 n-C4Hg 2182 CH3 3-(N-Methylaminoc~rbonyl)-C6H4 t-C4Hg 2183 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 n-C6Hl3 2184 CH3 3-(N-Methylam;noc~rbonyl)-C6H4 Prop-l-en-3-yl 2185 CH3 3-(N-Methylam;noc~rbonyl)-c6H4 (E)-1-Chloroprop-1-en-3-yl ~D
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Z ~ ~ ~ N ~I ~ ~ ~' No. R Rd Ak o 2207 CH3 2-Dimethylam;noc~rbonyl-C6H4 n-C6H13 ~
2208 CH3 2-Dimethylaminocarbonyl-C6H4 Prop-1-en-3-yl 2209 CH3 2-Dimethylaminqc~rbonyl-C6H4 ~E)-l-Chloroprop-l-en-3-yl O
2210 CH3 2-Dimethylam;nocArbonyl-C6H4 Propyn-3-yl 2211 CH3 2-Dimethylam;noc~rbonyl-C6H4 3-Methyl-but-2-en-1-yl 2212 CH3 3-Dimethylaminoc~rho~yl-C6H4 H
2213 CH3 3-Dimethylaminocarbonyl-C6H4 CH3 2214 CH3 3-Dimethylaminoc~rbonyl-c6H4 C2Hs 2215 CH3 3-Dimethylaminocarbonyl-C6H4 n-C3H7 2216 CH3 3-Dimethylaminoc~rbonyl-C6H4 i-C3H7 2217 CH3 3-DimethylaminocArhnnyl-C6H4 n-C4Hg P
2218 CH3 3-Dimethylam;nQc~rbonyl-c6H4 t-C4H9 2219 CH3 3-Dimethylaminocarbonyl-C6H4 n-C6H13 2220 CH3 3-Dimethylaminoc~rbonyl-C6H4 Prop-1-en-3-yl 2221 CH3 3-DimethylaminocArbonyl-C6H4 (E)-1-Chloroprop-1-en-3-yl 2222 CH3 3-Dimethyla~;nocArho~yl-C6H4 Propyn-3-yl 2223 CH3 3-Dimethylaminoc~rbo~yl-C6H4 3-Methyl-but-2-en-1-yl 2224 CH3 4-Dimethylam;noc~rbonyl-C6H4 H
2225 CH3 4-Dimethylam;noc~rbonyl-C6H4 CH
2226 CH3 4-Dimethylam;noc~r~onyl-c6H4 C2H5 C~
2227 CH3 4-Dimethylaminoc~-bonyl-C6H4 n-C3H7 Co 2~99422 ,. . ..
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Table 1251 Compounds of the general formula I.A (n 2 O) in which UR' i8 5 methoxyamino, VR~' is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1252 10 Co,.l~ounds of the general formula I.A (n = 0) in which UR' is ~ ethoxyamino, VR" i8 methoxy, ya iS -CHzO-# (-# = bond to Aa) and Aa corresponds to one of the y-v~S stated in Table A
Table 1253 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is ethoxy, ya is -CH20-# (-# = bond to Aa) and Aa corresponds to one of the yL~Up8 stated in Table A
20 Table 1254 Compounds of the general formula I.A (n 2 o) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2S-~ = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1255 Compounds of the general formula I.A (n = 0) in which UR' is ethoxyamino, VR" is methoxy, ya iS -CH=CH- and Aa corresponds to 30 one of the groups stated in Table A
; Table 1256 Compounds of the general formula I.A (n = 0) in which UR~ is 35 methoxyamino, VR" is methoxy, ya iS -OCH2-# (-# = bond to Aa) and Aa corresponds to one of the groups stated in Table A
Table 1257 40 Compounds of the general formula I.A (n = 0) in which UR' i5 methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is phenyl which carries a radical CH=NORiii in the 4 position, Riii for a co,..pound corresponding to one of the y~U~S stated in Table C
~1~942~
Table 1258 C~."~ ds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, Y~ is -CH20-# (-~ = bond to Aa) and S Aa is 2-methylphenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the ylo~s stated in Table C
Table 1259 Co,..~v~,lds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-$ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical CHsNORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
( Table 1260 Compounds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1261 Compounds of the general formula I.A ~n ~ 0) in which UR' i8 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa~ and Aa is 2,S-dimethylphenyl which carries a radical CH=N0Riii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
~, Table 1262 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -cH2o-# (-~ = bond to Aa) and Aa i8 2-methyl-5-chlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a cv,,,~o~nd corresponding to one of the groups stated in Table C
Table 1263 Co...~vullds of the general formula I.~ (n = 0) in which UR' is methoxyamino, VR" is methoxy, Y~ is -CH20-~ bond to Aa) and 45 Aa is 2-chloro-5-methylphenyl which carries a radical CH=NORiii in 2199~22 the 4 position, Riii for a compound corresponding to one o~ the y~OU~S stated in Table C
Table 1264 Cu...~unds of the general formula I.A (n z 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CH=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 1265 Compounds of the general formula I.A (n ~ 0) in which UR' is 15 methoxyamino, VRn is methoxy, ya is -CHzO-~ (-# - bond to Aa) and ( Aa is phenyl which carries a radical CH=NORiii in the 3 position, Riii for a c~ ou~d corresponding to one Of the groups stated in Table C
20 Table 1266 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical CH=NORiii in the 5 25 position, Riii for a cv...p~ul,d corresponding to one of the groups stated in Table C
Table 1267 30 Compounds of the general formula I.A (n 5 0) in which UR' i8 ~- methoxyamino, VR" is ~ethoxy, ya is -CH2O-~ = bond to A~) and . Aa is phenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the y~u~3 stated in Table C
Table 1268 Compounds of the general f ormula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to A~) and 40 Aa is 2-~ethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2199~22 Table 1269 C~ ou.lds o~ the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and 5 Aa is 2-fluorophenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1270 Compounds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 1271 Co,l.~ou,-ds of the general formula I.A (n - 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1272 Co~pounds of the general formula I.A (n - 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ ~ bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 30 C(CH3)=NORiii in the 4 position, Riii for a compound corresponding ~- to one of the groups stated in Table C
Table 1273 35 C~ /~unds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ (-* - bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CH3)sNORiii in the 4 position, Riii for a cc~.poulld corresponding to one of the groups stated in Table C
Table 1274 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -cH20 - ~ (-# 2 bond to Aa) and 45 Aa is 2,5-dichlorophenyl which carries a radical C(CH3)=NORiii in _ 478 2 1 9 9ll 2 2 the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1275 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# - bond to Aal and A~ is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups lO stated in Table C
Table 1276 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to Aa) and ( Aa is 2-methylphenyl which carries a radical C(CH3)=NORiii in the S position, Rili for a co~"~ound corresponding to one of the groups stated in Table C
20 Table 1277 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is phenyl which carries a radical C(CH2CH3)-NOR~ii in the 4 25 pos~tion, Riii for a compound corresponding to one of the groups stated in Table C
Table 1278 30 C~ ounds of the general formula I.A (n = O) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1279 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 40 Aa is 2-fluorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv..,~o~nd corresponding to one of the groups stated in Table C
2~99i22 Table 1280 Compounds of the general formula I.A (n s 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and 5 Aa is 2-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a col.lp~und corresponding to one of the groups stated in Table C
Table 1281 Compounds of the general ~ormula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the 15 groups stated in Table C
~' Table 1282 CG,..y~unds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# ~ bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH3)=NORiii in the 4 position, Riii for a cv..~o~ild corresponding to one of the groups stated in Table C
25 Table 1283 Co"l~ounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-* (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical 30 C(CH2CH3)-NoRiii in the 4 position, Riii for a c~...~,.d corresponding to one of the groups stated in Table C
Table 1284 35 C~ ounds of the general formula I.A (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, ya is -CH20-~ (-* = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CH2CH3)-NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1285 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-* (-# = bond to Aa) and 45 Aa is phenyl which carries a radical C(CH2CH3)=NORiii in the 3 ~ 2199122 position, Riii for a c~ vund corresponding to one of the yLvU~s stated in Table C
Table 1286 Co,,.~ounds of the general formula I.A (n = 0~ in which UR' is methoxyamino, VRn is methoxy, ya is -CH20-# ( -# 2 bond to Aa) and Aa i~ 2-methylphenyl which carries a radical C(CH2CH3)=NORiii in the 5 position, Riii for a co~..pv~nd corresponding to one of the 10 groups stated in Table C
Table 1287 CoI,.pounds of the general formula I.A (n 2 O) in which UR' is 15 methoxyamino, VR is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 1288 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in 25 the 4 position, Riii for a co.l,~o~"d corresponding to one of the groups stated in Table C
Table 1289 30 Compounds of the general formula I.A (n e o) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# - bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~.llpou"d corresponding to one of the groups stated in Table C
Table 1290 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is - CH20-# ( - # 2 bond to Aa) and 40 Aa is 2-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cvll,~ound corresponding to one of the y ~ OU~3 stated in Table C
U05~/45~U4 ~ 481 2199422 Table 1291 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-~ 5 bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1292 Cu,.l~o~l-ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# ( -# e bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CH2CH2CH3)=NORiii in the 4 position, Riii for a cG,..~ound 15 corresponding to one of the groups stated in Table C
( , .
Table 1293 C~..*ou~.ds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya is -CH20-# t-~ = bond to A~) and Aa is 2-chloro-5-methylphenyl which carrie~ a radical C(CH2CH2CH3)3NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1294 Compounds of the general for~~ I.A (n = 0) in which UR' i5 methoxyamino, VR~' is methoxy, ya iS -CH20~ = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical 30 C(CH2CH2CH3)=NORiii in the 4 position, Riii for a ~o,..~o~nd corresponding to one of the groups stated in Table C
~. .
Table 1295 35 Compounds of the general formula I.A (n 5 O) in which UR' is methoxyamino, VR~ is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH2CH2CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the stated in Table C
Table 1296 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# ~-~ = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1297 Compounds of the general formula I.A (n=0) in which UR' is ethoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CH2CH2CH3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1298 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1299 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1300 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1301 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
2:~99422 Table 1302 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# (-# = bond to Aa) and 5 Aa is 2,5-dimethylphenyl which carries a radical ClCH(CH3)2]=NOR
in the 4 position, Riii for a cv...~ound corresponding to one of the groups stated in Table C
Table 1303 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH2O-~ (-* = bond to Aa) and Aa is 2-methyl-S-chlorophenyl which carries a radical C[CH(CH3)2]=NORiii in the 4 position, Riii for a compound lS corresponding to one of the yLO~S stated in Table C
Table 1304 Co,.*oulLds of the general formula I.A (n = 0~ in which UR' is 20 methoxyamino, VR" i8 methoxy, ya i8 -CH20-# (-# 2 bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C~CH(CH3)2]=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1305 Compounds of the general formula I.A (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, ya i8 -CH20-# (~~ - bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical CtCH(CH3) 2]=NoRiii 30 in the 4 position, Riii for a ~v...~ou.ld corresponding to one of the groups stated in Table C
Table 1306 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# ~-~ = bond to Aa) and Aa is phenyl which carries a radical CtCH(CH3) 2 ]-NORiii in the 3 position, Riii for a ~."~ound corresponding to one of the groups stated in Table C
Table 1307 C~",~o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C[CH(CH3)2]=NORiii in , 2 1 994~2 the S position, Rii$ for a co~ ound corresponding to one of the groups stated in Table C
Table 1308 CG~ u~.ids of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a c~ und corresponding to one of the groups 10 stated in Table C
Table 1309 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6Hs)sNORiii in the 4 position, Riii for a compound corresponding to one of the yLo~s stated in Table C
20 Table 1310 Co...~oullds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -cH2o-# (~~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C(C6H5)2NORiii in the 25 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1311 30 Co,..~ur.ds of the general formula I.A (n = 0) in which UR~ i8 methoxyamino, VRn i8 methoxy, ya i8 -CH20-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Ri$$ for a col"~ound corresponding to one of the groups stated in Table C
Table 1312 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya iS -CH20-# (-# = bond to Aa) and 40 Aa is 2,5-dimethylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a col,.pound corresponding to one of the groups stated in Table C
Table 1313 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and 5 Aa i8 2-methyl-5-chlorophenyl which carries a radical C(C6H5)=NORiii in the 4 position, Riii for a ~Gr.~ nd corresponding to one of the groups stated in Table C
Table 1314 Compounds of the general formula I.A (n s 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Ri$i for a compound corresponding 15 to one of the groups stated in Table C
( Table 1315 Compounds of the general formula I.A (n - 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(C6Hs)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1316 Compounds of the general formula I.A ~n = 0) in which UR' is methoxyamino, VR~ is methoxy, ya i8 -cH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(C6H5~=NORiii in the 3 30 position, Riii for a compound corresponding to one o~ the yr Oh~S
stated in Table C
Table 1317 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(C6H5)=NORiii in the 5 position, Rii~ for a compound corresponding to one of the yl~u~R
stated in Table C
Table 1318 Compounds of the general for~ula I.~ (n = 0) in which UR' is ~ethoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and 45 Aa is phenyl which carries a radical C(Cl)=NORiii in the 4 ~, 2~99122 position, RLii for a ~o~ o~nd corresponding to one of the groups stated in Table C
Table 1319 C ,o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and A~ is 2-methylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a co."~o~lld corresponding to one of the groups 10 stated in Table C
Table 1320 C~m~u~lds of the general formula I.A (n = 0) in which UR' i8 1~ methoxyamino, VR is methoxy, ya i8 -CH20-# (-# = bond to Aa) and ( Aa is 2-fluorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a col.,~ound corresponding to one of the groups stated in Table C
20 Table 1321 Compounds of the general for.mula I.A ~n 5 0) in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(Cl)=NORiii in the 4 25 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1322 30 Compounds of the general formula I.A (n = 0) in which UR' is l methoxyamino, VRn is methoxy, ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a ~o..,~oulld corresponding to one of the groups stated in Table C
Table 1323 CoL,I~o~.,ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH2O-# (-~ = bond to Aa) and 40 Aa is 2-methyl-5-chlorophenyl which carries a radical C(Cl)=NOR
in the 4 position, Rii~ for a compound corresponding to one of the groups sta,ted in Table C
2199~22 Table 1324 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and 5 Aa is 2-chloro-5-methylphenyl which carries a radical C(Cl)=NORii~
in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1325 Compounds of the general formula I.A (n ~ 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(Cl)=NORiii in the 4 position, Riii for a C61LI~UI1d corresponding to one of the 15 groups stated in Table C
Table 1326 Compounds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa is phenyl which carries a radical C(Cl)=NORiii in the 3 position, Riii for a _ oulld corresponding to one of the ~L~U~S
stated in Table C
25 Table 1327 Co,l,pGundg of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is 2-methylphenyl which carries a rad~cal C(Cl)=NORiii in the 5 30 position, Rlii for a ~l~ound corresponding to one of the yLOu~g stated in Table C
Table 1328 35 Compounds of the general formula I.A (n = 0) in which UR~ is methoxyamino, VR~' is methoxy, ya iS -CH20-# (~~ = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a co~ Gu--d corresponding to one of the groups stated in Table C
Table 1329 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and 45 Aa is 2-methylphenyl which carries a radical C(SCH3)=NORiii in the 2199~2~
4 position, Riii for a co _u,ld corresponding to one of the y~vU~S
stated in Table C
Table 1330 s Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and Aa is 2-fluorophenyl which carries a radical C~SCH3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups 10 stated in Table C
Table 1331 Compounds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to Aa) and Aa is 2-chlorophenyl which carries a radical C(SCH3)=~ORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
20 Table 1332 C_ l~unds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# - bond to A~) and Aa is 2,5-dimethylphenyl which carries a radical C(SCH3)-NORiii in 25 the 4 position, Riii for a ~o,..~und corresponding to one o~ the groups stated in Table C
Table 1333 30 Compound~ of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-~ = bond to A~) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(SCH3)=NORiii in the 4 position, Riii for a ov,..~ound corresponding to one of the groups stated in Table C
Table 1334 C~l..p~u~lds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-# (-# ~ bond to A~) and 40 A~ is 2-chloro-5-methylphenyl which carr~es a radical C(SCH3) -N0Riii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
.
-00~0/452~4 g9~2~
48g Table 1335 Cu~ u~l~ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# - bond to Aa) and 5 Aa is 2,5-dichlorophenyl which carries a radical C(SCH3)-NORiii in the 4 position, Riii for a co...~ou.~d corresponding to one of the y~ps stated in Table C genannten GL ~p~er, entsprich Table 1336 Co,..~vul~ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and Aa is phenyl which carries a radical C(SCH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups 15 stated in Table C
Table 1337 Co,..~oul~ds of the general formula I.A (n = 0) in which UR' is 20 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-methylphenyl which carries a radical C(SCH3)-NORiii in the 5 position, Riii for a cv...~ou.~d corresponding to one of the groups stated in Table C
25 Table 1338 Compounds of the general formula I.A ~n = 0) in which UR' is methoxyamino, VR" ic methoxy, ya iS -CH20-# (-# = bond to Aa) and A~ is phenyl which carries a radical C(cyclopropyl)=NORiii in the 30 4 position, Riii for a compound corre~ponding to one of the yLv~
stated in Table C
Table 1339 35 C~ll.pounds of the general formula I.A (n = 0) in which UR' i methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)sNORiii in the 4 position, Riii for a cv,ll~ound corresponding to one of the groups stated in Table C
Table 1340 Compounds of the general formula I.A (n - 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ # = bond to Aa) and 45 Aa i8 2-fluorophenyl which carries a radical C(cyclopropyl)--NOR
9 ~ 2 2 in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1341 Cl ~o~nds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" i8 methoxy, ya iS -CH20-# (-~ = bond to Aa) and Aa iB 2-chlorophenyl which carries a radical C(cyclopropyl)=NOR
in the 4 position, Riii for a compound corresponding to one of the 10 groups stated in Table C
Table 1342 Cv~ ds of the general formula I.A (n = 0) in which UR' is 15 methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and ( Aa is 2,5-dimethylphenyl which carries a radical C(cyclopropyl)sNORiii in the 4 position, Riii for a cv,..~oulld corresponding to one of the groups stated in Table C
20 Table 1343 C~ ~u,.ds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-~ - bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical 25 C(cyclopropyl)=NORiii in the 4 position, Riii for a cvl.*ound corresponding to one of the groups stated in Table C
Table 1344 30 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(cyclopropyl)-NORili in the 4 position, Riii for a co...~u.,d corresponding to one of the groups stated in Table C
Table 1345 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-~ bond to Aa) and 40 Aa is 2,5-dichlorophenyl which carries a radical C(cyclopropyl)=NORiii in the 4 position, Riii ~or a cc~..~o~..d corresponding to one of the groups stated in Table C
2~99~22 Table 1346 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ # = bond to Aa) and 5 Aa is phenyl which carries a radical C(cyclopropyl)=NORiii in the 3 position, Riii for a c~ oul-d corresponding to one of the groups stated in Table C
Table 1347 Cor..~oùllds of the general formula I.A (n = 0) in which UR' i8 methoxyamino, VRn is methoxy, ya iS -CH20-# (-# s bond to Aa) and Aa is 2-methylphenyl which carries a radical C(cyclopropyl)=NORiii in the 5 position, Riii for a compound corresponding to one of the lS ylOU~S stated in Table C
( 'rable 1348 C~l,~o~nds of the general formula I.A (n 3 0) in which UR' is 20 methoxyamino, VRn iS methoxy, ya is -CH20-# (-# - bond to A~) and Aa is phenyl which carries a radical C(CF3)=NORi~i in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
25 Table 1349 CGmp~u,lds of the general formula I.A (n = 0) in which UR' is methoxyamino, VRn iS methoxy, ya is -CH20-# (-~ = bond to Aa) and Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 30 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 13S0 35 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and Aa i8 2-fluorophenyl which carries a radical C(CF3)=NORiii in the 4 ~osition, Riii for a compound corresponding to one of the groups stated in 'rable C
Table 1351 Compound~ of the general formula I.A (n = 0) in which UR' i~
methoxyamino, VR" is methoxy, ya i8 -CH20-# (-# = bond to A~) and 45 Aa is 2-chlorophenyl which carries a radical C(CF3)=NORii~ in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1352 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dimethylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1353 Compounds of the general formula I.A (n-0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-methyl-5-chlorophenyl which carries a radical C(CR3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1354 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2-chloro-5-methylphenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1355 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is 2,5-dichlorophenyl which carries a radical C(CF3)=NORiii in the 4 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1356 Compounds of the general formula I.A (n=0) in which UR' is methoxyamino, VR" is methoxy, Ya is -CH2O-# (-# = bond to Aa) and Aa is phenyl which carries a radical C(CH3)=NORiii in the 3 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1357 Compounds of the general formula I.A (n = 0) in which UR' is methoxyamino, VR" is methoxy, ya iS -CH20-# (-# = bond to Aa) and S Aa is 2-methylphenyl which carries a radical C(CF3)=NORiii in the 5 position, Riii for a compound corresponding to one of the groups stated in Table C
Table 1358 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH2S-# (-# = bond to Aa) and Aa is 1,3,4-oxadiazol-2-yl, the combination of the substituent in the 5 position of the oxadiazolyl ring and Xn corresponding for 15 each compound to a line of Table D
Table 1359 Compounds of the general formula I.A in which UR' is ~ 20 methoxyamino, VR is methoxy, ya iS -CH2S-# (-~ - bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 position of the thiazolyl ring and Xn corresponding for each c~r..~o~.ld to a line of Table D
25 Table 1360 Compounds of the general formula I.A in which UR' is methoxyamino, VR" i5 methoxy, ya iS -cH2o-# (-~ - bond to Aa) and Aa is thiazol-2-yl, the combination of the substituent in the 4 30 position of the thiazolyl ring and Xn corresponding for each , compound to a line of Table D
~...
Table 1361 35 Compounds of the general formula I.A in which UR' is methoxyamino, VRn is methoxy, ya i8 -CH20-# (-~ = bond to Aa) and Aa is 5-methylthiazol-4-yl, the combination of the substituent in the 2 position of the thiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1362 Co. oul,ds of the general formula I.A in which UR' is methoxyamino, VR~ is methoxy, Y~ is -CH2S-# (-~ = bond to Aa) and 4~ Aa is oxazol-2-yl, the combination of the substituent in the 4 -2199~22 position of the oxazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1363 C~ unds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, Y~ is -CH20-~ (-# = bond to Aa) and Aa is oxazol-2-yl, the c~mh~nation of the substituent in the 4 position of the oxazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 1364 Co~ G~nds of the general formula I.A in which UR' is 15 methoxyamino, VR" is methoxy, ya is -cH2s-# ~-# 2 bond to Aa) and Aa is 1,2,4-oxadiazol-5-yl, the co~h~ n~tion of the substituent in the 3 position of the oxadiazolyl ring and Xn corresponding for each compound to a line of Table D
20 Table 1365 Co~ ds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH20-~ (-# - bond to Aa) and Aa is 1,2,4-oxad~azol-5-yl, the combination of the substituent in 2~ the 3 position of the oxadiazolyl ring and Xn corre~ponding for each compound to a line of Table D
Table 1366 30 C~ o~-,ds of the general formula I.A in which UR' i8 methoxyamino, VR" is methoxy, ya iS -CH2S-~ ~-# ~ bond to Aa) and Aa is 1,2,4-thiadiazol-5-yl, the c~ h~nAtion of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1367 CG..I~ounds of the general formula I.A in which UR' is methoxyamino, VRn is methoxy, ya iS -CH20-~ (-# = bond to Aa) and 40 Aa i8 1,2,4-thiadiazol-5-yl, the cnmh;n~tion of the substituent in the 3 position of the thiadiazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1368 Compounds of the general formula I.A in which UR' is methoxyamino, VR~ is methoxy, ya i8 -CH2S-~ = bond to Aa) and 5 Aa is isoxazol-2-yl, the c~mh; n~tion of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each cG.t.~o~lld to a line of Table D
Table 1369 Co,..pounds of the general formula I.A in which UR' is methoxyamino, VR" i~ methoxy, ya is -CH20-# (-# = bond to Aa) and Aa is isoxazol-2-yl, the combination of the substituent in the 5 position of the isoxazolyl ring and Xn corresponding for each 15 compound to a line of Table D
Table 1370 Compounds of the general formula I.A in which UR' is 20 methoxyamino, VRn is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is isothiazol-2-yl, the combination of the substituent in the position of the isothiazolyl ring and Xn corresponding for each co~ o~nd to a line of Table D
25 Table 1371 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya i8 -CH20-~ (-# = bond to Aa) and Aa is isothiazol-2-yl, the combination of the substituent in the 5 30 position of the isothiazolyl ring and Xn corresponding for each co.,.~o~nd to a line of Table D
Table 1372 35 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa i8 pyrazol-3-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each compound to a line of Table D
Table 1373 CG...~vunds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH20~ = bond to Aa) and 45 Aa is pyrazol-3-yl, the combination of the substituent in the 1 496 2199~22 position of the pyrazolyl ring and Xn corresponding for each co..,~ou,~d to a line of Table D
Table 1374 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-~ s bond to Aa) and Aa i8 pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each 10 compound to a line of Table D
Table 1375 Compounds of the general formula I.A in which UR' is 15 methoxyamino ~ VRn i8 methoxy, ya is -CH20-~ (-# e bond to Aa) and Aa is pyrazol-4-yl, the combination of the substituent in the 1 position of the pyrazolyl ring and Xn corresponding for each c~,.,p~.,d to a line of Table D
20 Table 1376 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2S-# (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in 25 the 1 position of the 1,2,4-triazol ring and Xn corresponding for each c~,.,~o~nd to a line of Table D
Table 1377 30 Compounds of the general formula I.A in which UR' is methoxyamino, VR" is methoxy, ya is -CH2O-~ (-# = bond to Aa) and Aa is 1,2,4-triazol-3-yl, the combination of the substituent in the 1 position of the 1,2,4-triazol ring and Xn corresponding for each co1l,pound to a line of Table D
Table 1378 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb iS oxygen and Ab for a ~ d 40 corresponds to one of the groups stated in Table E
Table 1379 Compounds of the general formula I.B (n = 0) in which UR' is 45 methoxyamino, VR" is ethoxy, yb iS oxygen and Ab for a c~.,.~u~.d corresponds to one of the groups stated in Table E
2~9912~
Table 1380 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is sulfur and Ab for a compound corresponds to one of the groups stated in Table E
Table 1381 Compounds of the general formula I.B (n - 0) in which UR' is 10 methoxyamino, VRn is ethoxy, yb iS sulfur and Ab for a c~ ~und corresponds to one of the groups stated in Table E
Table 1382 15 CGrll~unds of the general formula I.B (n e O) in which UR' is ~~ methoxyamino, VR" is methoxy, yb is oxygen and Ab is phenyl, this phenyl radical carrying an - Oo~R~ group in the 3 position and the co~h;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1383 Co~ o~nds of the general formula I.B (n s 0) in which UR' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is phenyl, thi~
25 phenyl radical carrying an -Oo~R~ group in the 3 position and the cnmh~n~tion of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1384 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group 35 corresponding for each compound to a line of Table F
Table 1385 Co.,.~ -ds of the general formula I.B (n = 0) in which UR' is 40 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table F
498 2 ~ 9 9 ~ ~ 2 Table 13B6 Cofil~u~ds of the general. formula I.B ~n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyridyl, 5 this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the c~mh;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table Table 1387 Compounds of the general formula I.B (n = o) in which U~' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyridyl, this 2-pyridyl radical carrying an -Oo~R~ group in the 4 position and the combination of the index o and of the R~ group 15 corresponding for each cv.,.~ound to a line of Table F
Table 1388 C~l..pounds of the general formula I.B (n = 0) in which UR' i5 20 methoxyamino, VR" i~ methoxy, yb i8 oxygen and Ab 1~
pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the combination of the index o and of the R~ group corresponding for each c~"l~ ,d to a line of Table F
25 Table 1389 CG.,.~ou..ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VRn is ethoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
30 group in the 2 position and the comhin~tion of the index o and of the R~ group corresponding for each co.l.~u~.ld to a line of Table F
Table 1390 35 Compound~ of the general formula I.B (n = 0) in which UR' iB
methoxyamino, VR" is methoxy, yb is oxygen and Ab is 2-pyrazinyl, this 2-pyrazinyl radical carrying an -Oo~R~ group in the 6 position and the combination of the index o and of the R~ group corresponding for each c~ ,uund to a line of Table F
Table 1391 Cv...~o~lds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yb is oxygen and Ab is 2-pyrazinyl, 45 this 2 p~L azinyl radical carrying an -Oo~R~ group in the 6 , . . . .
~199~22 4g9 position and the aomh; nation of the index o and of the R~ group corresponding for each compound to a line of Table F
Table 1392 Cor,-~o~,ds o~ the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the cnmh;~~tion of the index o and of 10 the R~ group corresponding for each cG",~Gulld to a line of Table G
Table 1393 Cum~o~nds of the general formula I.B (n = 0) in which UR' is 15 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is ~~ pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 6 position and the combination of the index o and of the R~ group corresponding for each co,~,~ou~ld to a line of Table G
20 Table 1394 CGl,.~unds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radiaal carrying an - Oo~R~
25 group in the 4 position and the combination of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 1395 30 C- _unds of the general formula I.B (n = 0) in which UR' i8 methoxyamino, VR" is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an -Oo~R~
group in the 4 position and the combination of the index o and of the R~ group corresponding for each c~ ound to a line of Table G
Table 1396 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 40 pyrimidin-4-yl, thi3 pyrimidin-4-yl radical aarrying an -Oo~R~
group in the 2 position and the c~mh; n~tion of the index o and of the R~ group corresponding for each compound to a line of Table G
2199~2 Table 1397 Compounds of the general formula I.B (n = 0) in which UR' i5 methoxya~ino, VRn is ethoxy, yb iS oxygen and Ab i5 5 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an -Oo~R~
group in the 2 position and the cnmh;n~tion of the index o and of the R~ group corresponding for each compound to a line of Table G
Table 1398 Co~ Gu~,ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group 15 corresponding for each compound to the substituents stated in a ( line of Table H
Table 1399 20 Compounds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 6 position and the R~ group corresponding for each c~ ound to the substituents stated in a 25 line of Table H
Table 1400 Compounds of the general formula I.B (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy, yb i8 oxygen and Ab i8 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
Table 1401 Compounds of the general formula I.B (n z 0) in which UR' i8 methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is 40 pyrimidin-4-yl, this pyrimidin-4-yl radical carrying an R~-substituted phenoxy group in the 2 position and the R~ group corresponding for each compound to the substituents stated in a line of Table H
0050/45~4 ~ 501 2199422 Table 1402 C~ uu~ds of the general formula I.B (n = 0) in which UR' is methoxyamino, VR" is methoxy, yb is oxygen and Ab is 5 pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each ~ ..d to the substituents stated in a line of Table H
10 Table 1403 Co..,~uul-ds of the general formula I.B (n 2 O) in which UR' is methoxyamino, VRn is ethoxy, yb is oxygen and Ab is pyrimidin-2-yl, this pyrimidin-2-yl radical carrying an 15 R~-substituted phenoxy group in the 4 position and the R~ group f corresponding for each compound to the substituents stated in a line of Table H
Table 1404 CG.I.~ounds of the general formula I.B (n e O) in which UR' i5 methoxyamino, VR" is methoxy, yb iS oxygen and Ab is 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group 25 corresponding for each compound to the substituent~ stated in a line of Table H
Table 1405 30 Compounds of the general formula I.B (n e O) in which UR' is methoxyamino, VR" is ethoxy, yb iS oxygen and Ab is ( 1,3,5-triazin-2-yl, this 1,3,5-triazin-2-yl radical carrying an R~-substituted phenoxy group in the 4 position and the R~ group corresponding for each cv...~ound to the substituents stated in a 35 line of Table H
.
Table 1406 Compounds of the general formula I.C (n = 0) in which UR' is 40 methoxyamino, VR" is methoxy, yc ~s CHsC(Cl)-C(=0)-0-# (-# z bond to AC) and Ac for a co~ o~nd corresponds to a group of Table I.l ~5 -~ 502 2~99~22 Table 1407 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-o-# (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.l Table 1408 Cv...~oul-ds of the general formula I.C (n - 0) in which UR' is 10 ethoxyamino, VR" is ethoxy, yc i8 CH=C(Br)-C(=0)-# (-# = bond to AC) and Ac for a compound corresponds to a group of Table I.l Table 1409 15 Compounds of the general formula I.C (n = 0) in which UR' is ( methoxyamino, VR" is methoxy, yc is CH=c(Br)-c(=o)-o-# (-# = bond to AC) and Ac for a cv...~o~L~.d corresponds to a group of Table I.1 Table 1410 Co...pounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is cH=c(~r)-c(=o)-o-# (-# = bond to AC) and Ac for a ~-c...~ound corresponds to a group of Table I.1 25 Table 1411 Compounds of the general formula I.C (n = 0) in which UR' is ethoxyamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-0-# (-# = bond to AC) and Ac for a corl-~ound correspond~ to a group of Table I.l Table 1412 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc is CH=c(No2)-c(=o)-o-# (-# = bond 35 to AC) and Ac for a colllpo~L~,d corresponds to a group of Table I.1 Table 1413 CG~ vul~ds of the general formula I.C (n - 0) in which UR' is 40 methoxyamino, VR" is ethoxy, yc is CH=C(N02)-C(=0)-0-# (-# = bond to AC) and Ac for a cv~ ouLld corresponds to a group of Table I.l 0050/45~04 2199~22 Table 1414 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VRn is methoxy, yc is CH=C(Cl)-C(=O)-NH-# (-# = bond 5 to A~) and Ac for a compound corresponds to a group of Table I.2 Table 1415 CGl"~oullds of the general formula I.C (n = 0) in which UR' is 10 methoxyamino, VR" is ethoxy, yc is CH=c(cl)-c(=o)-NH-# (-# 2 bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1416 15 Co.~ou~ds of the general for~ul~ I.C (n = 0) in which UR' is methoxyamino, VR~ i8 methoxy, yc is CH-C(~r)-C(=O)- NH-# (-# =
bond to AC) and Ac for a cv,-~und corresponds to a group of Table I.2 20 Table 1417 Compounds of the general form~ I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH-C(Br)-C(=0)-NH-# (-# - bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1418 Compounds of the general formula I.C (n - 0) in which UR' is methoxyamino, VR~ i8 methoxy, yc is CH=C(CN)-C(=0)-NH-# (-# = bond 30 to AC) and Ac for a compound corresponds to a group of Table I.2 ( Table 1419 Compounds of the general formula I.C (n = 0) in which UR' is 35 methoxyamino, VR" is ethoxy, yc is CH=C(CN)-C(=0)-NH-# (-~ = bond to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1420 40 Co,!,~ou.,ds of the general formula I.C (n = 0) in which UR' ~8 methoxyamino, VR" is methoxy, yc is CH=C(N02)-C(=0)-NH-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 2199~22 Table 1421 Compounds of the general formula I.C (n = 0) in which UR' i9 methoxyamino, VR" is ethoxy, yc is CHzC(N02)-C(=0)-NH-~ (-# = bond 5 to AC) and Ac for a compound corresponds to a group of Table I.2 Table 1422 Col"~ounds of the general formula I.C (n ~ 0) in which UR' is 10 methoxyamino, VR" is methoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-# (-~ =
bond to AC) and Ac for a ~v...~o~nd corresponds to a grou~ of Table I.2 Table 1423 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH=C(Cl)-C(=0)-N(CH3)-~ (-# =
bond to AC) and Ac for a cv.~.poulld corresponds to a group of Table I.2 Table 1424 Compounds of the general formula I.C (n 2 0) in which UR' is methoxyamino, VR" is methoxy, yc is CHsC(Br)-C(-0)-N(CH3)-# (-# =
Z5 bond to AC) and Ac for a co.,.~ound corresponds to a group of Table I.2 Table 1425 30 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VRn is ethoxy, yc i~ CH=C(Br)-C(=0)-N(CH3)-# (-~ =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 35 Table 1426 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc is CH=C(CN)-C(=0)-N(CH3)-# (-# =
bond to AC) and AC for a compound corresponds to a group of Table 40 I.2 -2199~22 Table 1427 Compounds of the general formula I.C (n = 0) in which UR' is methoxyamino, ~R" is ethoxy, Y~ is CH=C(CN)-C(=0)-N(CH3)~
5 bond to A~) and A~ for a cv.~.~und corresponds to a group of Table I.2 Table 1428 10 C~.-~oul-ds of the general formula I.C (n = 0) in which UR' is methoxyamino, VR" is methoxy, yc i8 CH=C(NO2)-C(=O)-N(CH3)-~ (-# =
bond to AC) and Ac for a compound corresponds to a group of Table I.2 15 Table 1429 CG~ unds of the general for~l~l A I.C (n = 0) in which UR' is methoxyamino, VR" is ethoxy, yc is CH-C(N02)-C(=0)-N~CH3)-# (-# =
bond to AC) and Ac for a compound corresponds to a group of Table 20 I.2 Table 1430 CG.,Ipou~lds of the general formula I.D (n = 0) in which UR' is 25 methoxyamino, VR" is methoxy and Ad for a co~l~y~u~ld corresponds to a group of Table J
Table 1431 30 Compounds of the general formula I.D (n = 0) in which UR' is - methoxya~ino, VR" i8 ethoxy and Ad for a cv.. ~ound corresponds to a ( group of Table J
Table 1432 Compounds of the general formula I.E (n = 0) in which UR' is methoxyamino, VR" is methoxy, ye -CH=N0-~ (-# = bond to Ae) and Ae for a compound corresponds to a group of Table K.l 40 Table 1433 Compounds of the general formula I.E (n = 0) in which UR' is methoxyamino, VR" is ethoxy, ye - CH=NO-# ( ~~ = bond to Ae) and AQ
for a compound corresponds to a group of Table K.1 0050/4520g .
506 2~99422 Table 1434 Compounds of the general formula I.E (n s 0) in which UR' is methoxyamino, VR" i8 methoxy, ye -cH=N-NH-# (-~ = bond to Ae) and 5 A~ for a ~~vmpo~nd corresponds to a group of Table K.2 Table 1435 Compounds of the general formula I.E (n = 0) in which UR' is 10 methoxyamino, VR" is ethoxy, ye -CH=N-NH-# (-# = bond to Ae) and Ae for a ~v...~nd corresponds to a group of Table K.2 Table 1436 15 C ~Lounds of the general form~ I.F (n z 0) in which UR' is ( methoxyamino, VRn is methoxy and Af is the radical -N=CRgRh, Rg being methyl and Rh for a cor..pou.~d corresponding to a group of Table L
20 Table 1437 C~ _ unds of the general formula I.F (n = 0) in which UR' i~
methoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being methyl and Rh for a c~ ound corresponding to a group of 25 Table L
Table 1438 Compounds of the general formula I.F (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy and Af is the radical -N-CRgRh, R9 ~- being ethyl and Rh for a c~.~l~ou~.d correspon~ng to a group of Table L
Table 1439 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg being ethyl and Rh for a compound corresponding to a group of Table L
Table 1440 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is methoxy and Af is the radical -N=CRgRh, R9 45 being n-propyl and Rh for a cGI,,po~nd corresponding to a group of Table L
2I99~22 Table 1441 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CRgRh, Rg 5 being n-propyl and Rh for a compound corresponding to a group of Table L
Table 1442 10 cor..pounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is methoxy and Af is the radical -N=CR9Rh, Rg being cyclo~op~l and Rh for a c~...~ulld corresponding to a group of Table L
15 Table 1443 Col..pou.lds of the general formula I.F (n 5 O) in which UR' is methoxyamino, VR" is ethoxy and Af i~ the radical -N=CRgRh, Rg being cyclopropyl and Rh for a compound corresponding to a group 20 of Table L
Table 1444 Co.--pounds of the general formula I.F (n = 0) in which UR' is 25 methoxyamino, VR" is methoxy and Af i5 the radical -N=CR9Rh, Rg being CF3 and Rh for a compound corresponding to a group of Table L
Table 1445 - Compounds of the general formula I.F (n = 0) in which UR' ismethoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being CF3 and Rh for a compound corresponding to a group of Table L
Table 1446 Co...~oullds of the general formula I.F (n = 0) in which UR' is methoxyamino, VRn is methoxy and Af i5 the radical -N=CRgRh, Rg 40 being methylthio and Rh for a co..l~o~d corresponding to a group o~
Table L
508 ~ I 9 9 ~ 2 2 Table 1447 Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VRn i8 ethoxy and Af is the radical -N=CR9Rh, R9 5 being methylthio and Rh for a col,l~oul~d corresponding to a group of Table L
Table 1448 10 compounds of the general formula I.F (n = 0) in which UR' iB
methoxyamino, VR" is methoxy and Af is the radical -N~CR9Rh, Rg being cyano and Rh for a compound corresponding to a group of Table L
15 Table 1449 f Compounds of the general formula I.F (n = 0) in which UR' is methoxyamino, VR" is ethoxy and Af is the radical -N=CR9Rh, R9 being cyano and Rh for a compound corresponding to a group of 20 Table L
Table 1450 Compounds of the general formula I.G (n = 0) in which UR' is -25 methoxyamino, VR" is methoxy, Yg is oxygen and Ag for a compound corresponds to a group of Table M
Table 1451 30 Compounds of the general formula I.G (n = 0) in which UR' i8 ! methoxyamino, VRn is ethoxy, Yg iB oxygen and A9 for a ~o.. ~ound corresponds to a group of Table M
Table 1452 Compounds of the general formula I.G (n = 0) in which UR' i5 methoxyamino, VR~ is methoxy, Y9 is sulfur and Ag for a compound corresponds to a group of Table M
40 Table 1453 Compounds of the general formula I.G (n = 0) in which UR' iB
methoxyamino, VR" is ethoxy, Yg i~ sulfur and Ag for a co...~ound corresponds to a group of Table M
-~. og 2199~22 Table 1454 Compounds of the general formula I.H (n = m = 0) in which UR' is methoxyamino, VR" is methoxy and Ah for a c~".~ound corresponds to 5 a group of Table N
Table 1455 Compounds of the general formula I.H (n = m = 0) in which UR' is 10 methoxyamino, VR" is ethoxy and Ah for a ~o..~oul.d corresponds to a group of Table N
Table 1456 15 Co..lp~nds of the general formula I.K (n = 0) in which UR' is methoxyamino, VR" is methoxy, Rf is hydrogen and the combination of the substituents Ret Rd and Ak corresponds for each co...~ound to a line of Table 0 20 Table 1457 Compounds of the general formula I.K (n = 0) in which UR' is methoxyamino, VR" i8 ethoxy, Rf i8 hydrogen and the combination of the substituents Ret Rd and Ak corresponds for each compound to a 25 line of Table 0 Table 1458 Compounds of the general formula I.A (n = 0) in which UR' is 30 methoxyamino, VR" is methoxy, ya is CH=CH- and Aa i8 a - heterocyclic structure, this heterocyclic structure corresponding for each co~"~ound to a line of Table D.l Table 1459 Compounds of the general formula I.A (n = 0) in which UR' i3 methoxyamino, VR" is ethoxy, ya iS CH=CH- and Aa is a heterocyclic structure, this heterocyclic structure corresponding for each co."~o~nd to a line of Table D.1 The novel c~ ou~ds of the formula I are suitable for controlling harmful fungi and An;r-l pests from the class comprising insects, arachnids and nematodes. They can be used in crop protection and 45 in the hygiene, material protection and veterinary sectors as fungicides and pesticides.
.
219~2 The insect pests include:
from the order of the butterflies (Lepidoptera), for exa~ple Adoxophyes orana, Agrotis ypsilon, Agrotis segetum, Alabama 5 argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Cacoecia murinana, Capua reticulana, Choristoneura fumiferana, Chilo partellus, Choristoneura occidentalis, Cirphis unipuncta, Cnaphalocrocis me~i n~l; S ~
Crocidolomia binotalis, Cydia pomonella, Dendrolimus pini, 10 Diaphania nitidalis, Diatraea grandiosella, Earias insulana, palpus lignosellus, Eupoecilia ambiguella, Feltia-subterranea, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, ~eliothis zea, Hellula lln~ s~ Hibernia defoliaria, Hyphantria cunea, Hyponomeuta 15 malinellus, Keiferia lycopersicella, Lambdina fiscellaria, f Laphygma exigua, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Manduca sexta, Malacosoma neustria, Mamestra brassicae, Mocis repanda, Operophthera 20 brumata, Orgyia pseudotsugata, O~trinia nubilalis, Pandemis heparana, Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Phyllocnistis citrella, Pieri~ brassicae, Plathypena scabra, Platynota stultana, Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodenia ornithogalli, Pseudoplusia 25 includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sesamia inferens, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Syllepta derogata, Synanthedon myopaeformis, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Tryporyza incertulas, Zeiraphera 30 canadensis, also Galleria mellonella and Sitotroga cerealella, c Ephestia cautella and Tineola bisselliella;
from the order of the beetles (Coleoptera), for ~Y~mrle Agriotes lineatus, Agriotes obscurus, Anthonomus grandis, Anthonomus 3s pomorum, Apion vorax, Atomaria linearis, Blastophagus piniperda, Cassida nebulosa, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchus napi, Chaetocnema t;h;~l1s, Conoderus vespertinus, Crioceris asparagi, Dendroctonus refipennis, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, 40 Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus bras;l;~nsis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus C~JI'~ ; S, Meligethes aeneus, Melolontha 45 h1ppocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllopertha horticola, Phyllophaga sp., Phyllotreta 511 23 99~2~
chrysocephala, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Psylliodes napi, Scolytus intricatus, Sitona lineatus, also Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Sitophilus granaria, La5ioderma serricorne, Oryzaephilus 5 surinamensis, Rhy~opertha dominica, Sitophilus oryzae, tribolium castaneum, Trogoderma granarium and Zabrotes subfasciatus;
from the order of the Diptera, for ~Y~mple Anastrepha ludens, Ceratitis capitata, Contarinia sorghicola, Dacus cucurbitae, 10 Dacus oleae, Dasineura brassicae, Delia coarctata, Delia radicum, Hydrellia griseola, Hylemyia platura, Liriomyza sativae;
Liriomyza trifolii, Mayetiola destructor, Orseolia oryzae, Oscinella frit, Pegomya hyoscyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis 15 pomonella, Tipula oleracea, Tipula paludosa, also Aedes aegypti, Aedes vexans, Anopheles maculipennis, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, 20 Haplodiplosis equestris, Hypoderma lineata, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Musca domestica, Muscina stabulans, Oestrus ovis, Tabanus bovinus and Simulium damnosum;
from the order of the Thysanoptera, for example Fr~nk~ n; ella 25 fusca, Frankliniella occidentalis, Fr~nkl;n;ella tritici, Haplothrips tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
~rom the order of the Hymenoptera, for e~r~ e Athalia rosae, 30 Atta cephalotes, Atta sexdens, Atta t~Y~n~, Hoplocampa minuta, Hoplocampa testudinea, Iridv,,.yl ~~ humilis, Iridomyrmex purpureus, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta and Solenopsis richteri;
35 from the order of the Heteroptera, for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus hesperus, Lygus lineolaris, Lygus pratensis, Nezara viridula, 40 Piesma quadrata, Solubea insularis and Thyanta perditor;
from the order of the Homoptera, for ~mple Acyrthosiphon onobrychis, Acyrthosiphon pisum, Adelges laricis, Aonidiella aurantii, Aphidula nasturtii, Aphis fabae, Aphis gossypii, Aphis 45 pomi, Aulacorthum solani, Bemisia tabaci, Brachycaudus cardui, Brevicoryne brassicae, Dalbulus maidis, Dreyfusia nor~-nn;anae, Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosoma ~ ................................... ~.... ..
219g~22 lanigerum, Laodelphax striatella, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzus persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Perkinsiella saccharicida, Phorodon humuli, 5 Planococcus citri, Psylla mali, Psylla piri, Psylla pyricol, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Saissetia oleae, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogatella furcifera, Toxoptera citricida, trialeurodes abutilonea, trialeurodes vaporariorum and Viteus vitifolii;
from the order of the termites (Isoptera), for example C~lotermes flavicollis, Leucot ~s flavipes, Macrot~rm~s subhyalinus, Odontotermes formosanus, Reticulitermes lucifugus and Termes natalensis;
from the order of the Orthoptera, for example Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, 20 Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Schistocerca gregaria, also Acheta domestica, Blatta orientalis, Blattella germanica and Periplaneta americana;
from the order of the Arachnoidea, for ex~ _le phytophagous 25 mite~, such as Aculops lycopersicae, Aculops pelekassi, Aculus schlechtendali, Brevipalpus phoenicis, Bryobia praetiosa, Eotetranychus carpini, Eutetranychus banksii, Eriophyes sheldoni, Oligonychus pratensis, Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Tarsonemus 30 pallidus, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranchus pacificus, Tetranychus urticae, ticks such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes 35 rubicundus, Ornithodorus moubata, Otobius megnini, Rhipicephalus appendiculatus and Rhipicephalus evertsi, and zooparasitic mites, such as Dermanyssus g~ n~e, Psoroptes ovis and Sarcoptes scabiei;
40 from the class of the nematodes, for example root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, and Meloidogyne javanica, cyst-forming nematodes, eg. Globodera pallida, Globodera rostochiensis, Heterodera avenae, Heterodera glycines, and Heterodera schachtii, migratory endoparasites and 45 semiendoparasitic nematodes, eg. Heliocotylenchus multicinctus, Hirsch~-nn;ella oryzae, Hoplolaimus spp, Pratylenchus brachyurus, Pratylenchus fallax, Pratylenchus penetrans, Pratylenchus vulnus, .
0050~45204 21994~2 Radopholus similis, Rotylenchus reniformis, Scutellonema brady~, and Tylenchulus semipenetrans, leaf and stem nematodes, eg.
Anguina tritici and Aphelenchoides besseyi, Ditylenchus angustus, and Ditylenchus dipsaci, virus vectors, eg. Longidorus spp, 5 Trichodorus christei, Trichodorus viruliferus, Xiphinema index and Xiphinema mediterraneum.
The active ingredient can be used as such, in the form of their form~llAtions or the application forms prepared therefrom, for 10 example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents, granules, by spraying, nebulizing, dusting, broadcasting or pouring. The application forms depend entirely on the intended uses; they should in any 15 case ensure very fine distribution of the novel active ingredients.
Some of the compounds of the formula I have systemic fungicidal activity. They can be used as foliar and soil fungicides against 20 a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phy~v~l~y~2tes and Basidiomycetes.
They are particularly important for controlling a large number of 25 fungi on various crops, such as wheat, rye, barley, oats, rice, maize, lawns, cotton, soybean, coffee, sugar cane, grapevines, fruit trees, ornamentals and vegetable plants, such as cucumbers, beans and cucurbitaceae, as well as on the seeds of these plants.
30 The cv,,.~oul.ds I are particularly suitable for controlling the ~- following plant diseases:
* Erysiphe graminis (powdery mildew) in cereals, * Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbitaceae, * Podosphaera leucotricha on apples, * Uncinula necator on grapevines, * Puccinia species on cereals, * Rhizoctonia species on cotton and lawns, 40 * Ustilago species on cereals and sugar cane, * Venturia inaequalis (scab) on apples, * Helminthosporium species on cereals, * Septoria nodorum on wheat, * Botrytis cinerea (gray mold) on strawberries and grapevines, 45 * Cercospora arachidicola on peanuts, * Pseudocercosporella herpotrichoides on wheat and barley, * Pyricularia oryzae on rice, .
OU50/45Z~4 ~ 514 21 ~9~2~
* Phytophthora infestans on potatoes and tomatoes, ~ Fusarium- and Verticillium species on various plants, * Plasmopara viticola on grapevines, * Alternaria species on vegetables and fruit.
The novel compounds may also be used in material protection twood preservation), for e~mrle against Paecilomyces variotii.
They can be converted into the conventional formulations, such as 10 solutions, emulsions, suspensions, dusts, powders, pastes or granules. The application forms depend on the particular intended use; they should in any case ensure very fine distribution of the active ingredients.
15 The formulations can be prepared in a known manner, for ~YAmple by extending the active ingredient with solvents and/or carriers, if desired with the use of emulsifiers and dispersants, it being possible also to use other organic solvents as auxiliary solvents when water is used as a diluent.
Suitable assistants for this purpose are essentially:
- solvents, such as aromatics (eg. xylene), chlorinated aromatics ~eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol and butanol), ketones (eg.
cyclohexanone)~ amines (eg. ethanolamine and dimethylfor~-~;de) and water;
- carriers, such as crushed natural minerals (eg. kaolins, al~ n~Q, talc and chalk) and crushed synthetic minerals (eg.
finely divided silica and silicates);
- emulsifiers, such as nonionic and anionic emulsifiers (eg.
polyoxyethylene fatty alcohol ethers, alkanesulfonates and arylsulfonates) and - dispersants, such as ligninsulfite waste li~uors and methylcellulose.
Suitable surfactants are alkali metal, ~lk~l~ne earth metal and ammonium salts of aromatic sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of 40 fatty acids, alkanesulfonates and alkylarylsulfonates, alkylsulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of 45 naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol polyglycol ethers, .~
_ 515 2~99~22 tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, 5 sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Aqueous application forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation 10 of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adherents, dispersants or emulsifiers.
However, it is also possible to prepare concentrates which consist of active ingredient, wetting agents, adherents, 15 dispersants or emulsifiers and possibly solvent or oil and which ( are suitable for dilution with water.
Powders, broadcasting agents and dusting agents can be prepared by mixing or by m; 11 i ng the active ingredients together with a 20 solid carrier.
Granules, for ~mrl e coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
Solid carriers are minerals, such as silica gels, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate and magnesium oxide, milled plastics, fertilizers, such as 30 ammonium sulfate, A -nium phosphate, r ;um nitrate and ureas, f- and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.
The active ingredient concentrations in the ready-to-use formulations can be varied within relatively wide ranges.
Very generally, the compositions contain from 0.0001 to 95~ by weight of active ingredient.
Formulations contA;n;ng more than 95% by weight of active 40 ingredient can be successfully applied by the ultra-low-volume (ULV) method, in which case it is even possible to use the active ingredient without additives.
For use as fungicides, concentrations of from 0.01 to 95, 45 preferably from 0.5 to 90, % by weight of active ingredient are advisable. For use as insecticides, formulations cont~;n;ng from 2199~22 0.0001 to 10, preferably from 0.01 to 1, ~ by weight of active ingredient are suitable.
The active ingredients are usually used in a purity of from 90 to 5 100%, preferably from 95 to 100% (according to NMR spectrum).
Examples of such formulations are:
I. a solution of 90 par~s by weight of a novel cv.. ~ound I
and 10 parts by weight of N-methyl-~-pyrrolidone, which solution is suitable for use in the form of very fine drops;
II. a solution of 20 parts by weight of a novel compound I in a mixture of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanololeamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the formulation in water;
III. a solution of 20 parts by weight of a novel compound I in a mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the _ formulation in water;
IV. an aqueous dispersion of 20 parts by weight of a novel c~ ound I in a mixture of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction boiling within the range from 210 to 280 C and 10 part~ by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil; a dispersion is obtained by finely distributing the formulation in water;
V. a mixture milled in a hammer mill and comprising 20 parts by weight of a novel c~...~o~nd I, 3 parts by weight of the sodium salt diisobutylnaphtalene-~-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor and 60 parts by .
~99~22 weight of silica gel powders; a spray liquor is obtained by finely distributing the mixture in water VI. a thorough mi~ture of 3 parts by weight of a novel compound I and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient;
VII. a thorough mixture of 30 parts by weight of a novel cG"~ound I, 92 parts by weight of silica gel powder and 8 parts by weight of liquid paraffin which was sprayed onto the surface of this silica gel; this formulation imparts good adhesive capability to the active ingredient;
15 VIII. a stable aqueous dispersion of 40 parts by weight of a novel co,..~ .d I, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which dispersion can be further diluted;
IX. a stable oily dispersion of 20 parts by weight of a novel c~ ound I, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil;
X. a mixture milled in a hammer mill and comprising 10 parts by weight of a novel ~v.. ~ound I, 4 parts by weight of the f- sodium salt of diisobutylnaphthalene-a-sulfonic acid, 20 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, 38 parts by weight o~ silica gel and 38 parts by weight of kaolin; a spray liquor which contains 0.1% by weight of the active ingredient is obtained by finely distributing the mixture in 10,000 parts by weight of water.
The co~ Gu..ds I are applied by treating the fungi or the seeds, 40 plants or materials to be protected from fungal attack or the soil where the fungicidal amount of the active ingredients.
Application is effected before or after infection of the materials, plants or seed by the fungi.
~ 2~99~2~
The application rates are from 0.02 to 3, preferably from 0.1 to 1, kg of active ingredient per ha, depending on the type of effect desired.
5 In the seed treatment, amounts of active ingredient are from 0.001 to 50, preferably from 0.01 to 10, g per kilogram of seed are generally required.
The application rate of active ingredient for controlling pests 10 under open air conditions i8 from 0.02 to 10, preferably from 0.1 to 2.0, kg/ha of active ingredient.
The compounds I, alone or in combination with herbicides or fungicides, may also be applied mixed together with further crop 15 protection agents, for ~mple with growth regulators, pesticides or bactericides. The miscibility with fertilizers or with mineral salt solutions which are used for el; mi nating nutrient and trace element deficiencies is also of interest.
20 The crop protection agents and fertilizers may be added to the novel compositions in a weight ratio of from 1:10 to 10:1, if desired also immediately before use (tank mix). Mixing with fungicides or insecticides often results in a broadening of the fungicidal action spectrum.
The followin~ list of fungicides together with which the novel co.,.~ounds may be applied is intended to illustrate the possible combinations but not to restrict them:
30 sulfur, dithiocarbamates and derivatives thereof, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc 35 (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate) and N,N'-polypropylenebis(thiocarbamoyl) disulfide; nitro derivatives, such as dinitro-(l-methylheptyl)-phenyl crotonate, 40 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate and diisopropyl 5-nitroisophthalate;
heterocyclic substances, such as 2-heptadecyl-2-imidazoline 45 acetate, 2,4-dichloro-6-(o-chloro~ n; 1 i ~o ) -8-triazine, O,0-diethyl phth~l;midophosphonothioate, 5-a-mino-~ [bis-(dimethylamino) phosphinyl]-3-phenyl-1,2,4-triazol, 2,3-dicyano-1,4-dithio-2~99122 519anthraquinone, 2-thio-1,3-dithiolo-~-[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonyl-aminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydro-5 phthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-10 3-methyl-5-isoxazolone, 2-thiopyridine l-oxide, 8-hyd~uxy~inoline and its copper ~alt, 2,3-dihydro-5-carbox~n~l;do-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboYAn;l;do-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carbo~n;l;de, 2-methylfuran-15 3-carbox~n;l;de~ 2,5-dimethylfuran-3-carbox~n;l;de, 2,4,5-trimethylfuran-3-carbo~An~l;de, N-cyclohexyl-2,5-dimethyl-furan-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine 2,2,2-trichloroethylacetal, 20 piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)-formamide, 1-(3,4-dichloro~n;l;no)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and it~ salts, 2,6-dimethyl-N-cyclodedecylmorpholine and its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-25 2,6-dimethylmorpholine, N-t3-(p-tert-butylphenyl)-2-methyl-propyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, 1-t2-(2,4-dichloro-phenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea, 30 1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanone, 1-~4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanol, ~-(2-chlorophenyl)-a-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-me~hyl-pyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis-35 (3-ethoxycarbonyl-2-thioureido)benzene and 1,2-bis(3-methoxy-carbonyl-2-thioureido)-benzene~
and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide, 40 hexachlorobenzene, methyl DL-N-(2,6-dimethylphenyl)-N-furoylalaninate, methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxy-acetyl)-alaninate, N-(2,6-dimethylphenyl)-N-chloro-acetyl-D, L-2-aminobutyrolactone, methyl DL-N-(2,6-dimethyl-phenyl)-N-(phenylacetyl)-alaninate, 5-methyl-5-vinyl-3-(3,5-45 dichloro-phenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichloro-phenyl]-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, ~1~9~22 N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-~N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-lH-1,2,4-triazole, 2,4-difluoro-a-(lH-1,2,4-triazol-1-ylmethyl)-5 benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine and l-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-lH-l~2~4-tria2ole.
Synthesis Examples ~he methods described in the synthesis ~mples below were used for obt~in;ng further c~,upG~..ds I, with appropriate modification of the starting compounds. The compounds thus obtained are shown in the subsequent table together with physical data.
Example 1 Methyl a-methoxy-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~" CH(OCH3)--C02CH3 CH20-(2-CH3-C6Hs) 25 1.1 0.5 g of sodium borohydride was added a little at a time to 14.2 g of methyl ~-t2-(2-methylphenG~y ~~hylene)-phenyl]-~-ketoacetate in 110 ml of methanol while cooling at -20 C. After one hour at -15 C, the mixture was allowed to warm up to 0 C, and a total of 18.5 g of 7%
strength hydrochloric acid were added dropwise to the reaction mixture. The mixture thus obtained was substantially freed from the ~olvent under redu~ed preYsure. The residue obtained wa~ taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 14.2 g of methyl a-hydroxy-~-~2-(2t-methylphenoxymethylene)phenylacetate were obtained as an oil [IR (cm~l)s 1740, 1496, 1454, 1438, 1242, 1190, 1122, 1075, 1052, 752].
, 40 1.2 A solution of 2.86 g of the product from 1.1 in 30 ml of dimethylfor~- ;de was added dropwise at 0 C to a mixture of 0.26 g of sodium hydride and 10 ml of dimethylformamide. The mixture thus obtained was heated at about 3~ C for 10 minutes in an ultrasonic bath, a clear solution forming. 2.84 g of methyl iodide in 10 ml ~ ~19~22 of dimethylformamide were added to this solution at about 25-C.
After about 12 hours, the mixture was taken up with 300 ml of dilute sodium chloride solution. After extraction with tert-butyl methyl ether, working up of the organic phase and flash chromatography tS:l cyclohexane/tert-butyl methyl ether], 1 g of the target c~ ound was obtained [IR (cm~1): 1753, 14g6, 1461, 1453, 1436, 1241, 1193, 1121, 1013, 751].
Example 2 Methyl ~-methoxy-a-{2-t2-methyl-4-(1-methoximinoethyl)-phenoxymethylene]-phenyl}acetate (E) ~" CH(OCH3)--CO2CH3 ~ CH2O ~ C(CH3)=NOCH3 2.1 8.6 g of methyl a-hydroxy-~-[2-methoxymethylenephenyl]
acetate were obtained from 10.4 g of methyl a-t2-methoxymethylenephenyl]-a-ketoacetate and 0.5 g of sodium borohydride in 100 ml of diethylene glycol dimethyl ether by a method s~m~ 1 ~r to that described in 1.1 tlH-NMR (ppm): 3.35(s,3H); 3.75(s,3H); 4.11(d,1H)j 4.55(AB,2H); 5.42(d,1H); 7.25-7.4(m,4H)].
2.2 3.9 g of methyl ~-methoxy-a-t2-methoxymethylenephenyl]-acetate were obtained from 6.1 g of the product from 2.1 and 8.2 g of methyl iodide in a total of 110 ml of dimethylformamide by methods similar to that described in 1.2 [IR (cm~l): 1752, 1452, 1436, 1195, 1172, 1113, 1102, 1013, 752].
2.3 4 g of hydrogen bromide were added to 4.9 g of the product from 2.2 in 65 ml of methylene chloride at from -5 C to 0 C. After 12 hours at 0 C, the solvent was removed at reduced pressure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 5.4 g of methyl a-methoxy-~-[2-bromomethylphenyl]acetate were 2~g9il22 obtained [IR (cm~l): 1753, 1435, 1273, 1195, 1171, 1109, 1012, 762].
2.4 A mixture of 0.63 g of 2-methyl-4-(1-methoxyimino-ethyl)phenol, 0.96 g of the product from 2.3, 7.3 g of potassium carbonate and 25 ml of dimethylformamide was stirred for 2 hours at 50 C. After 12 hours at about 25 C, the solvent was removed at reduced pressure. The residue was taken up in tert-butyl methyl ehter. After purifying the organic phase with water, drying and evaporating down, 1 g of the target compound (mp.
76-78 C) was obtained.
Example 3 lS Methyl a-methoxy-a-{2-([1'-(4"-Chlorophenyl)-1'-methyl]iminoxy-methyl)phenyl}acetate (E) ~" CH~OCH3)--CO2CH3 ~ fi~
CH20N=C(CH3) ~ Cl 0.6 g of the target compound was obtained from 0.7 g of 25 4-chloroacetophenone oxime, 1.0 g of the product from 2.3, 0.1 g of sodium hydride and a total of 20 ml of dimethylformamide by methods si~ilar to that described in 2.4 tIR (cm~l): 1753, 1491, 1195, 1172, 1114, 1097, 1013, 929, 830, 755].
30 Example 4 Ethyl a-ethoxy-a-~2-(2-methylphenoxymethylene)phenyl]acetate 3~ ~ C~(OC~C 3)CO2C~zC~3 E~3C
4.1 Carbon tetrabromide was added a little at a time to a mixture of 6 g of the product from 1.1 and 60 ml of acetonitrile at O C. After lS minutes at O C, 6 g of triphenylphosphine were added. After 12 hours at 25 C, the reaction mixture was filtered. Evaporating down the filtrate gave the crude product, which was purified by means of flash chromatography ~10:1 cyclohexane/
~99~22 tert-butyl methyl ether]. 5.7 g of methyl ~-bromo-a-[2-(2-methylphenoxymethylene)phenyllacetate were obtained (mp. 79-81 C).
5 4.2 A mixture of 1.18 g of sodium ethylate in 2.57 g of ethanol was added to a mixturè of 5.2 g of the product from 4.1 and 35 ml of ethanol at about 25 C. After 2 hours at 60 C, the reaction mixture was freed from solvent at reduced pressure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 2.4 g of the target compound were obtained [1H-NMR (~/ppm):
11-13(m,6H); 2.25(s,3H); 3.4-3.65(m,2H); 5.18(s,1H);
5.25(AB,2H); 6.8-7.6(M,8H)].
Example 5 Methyl a-methoxy-a-t2-(2-methylphenoxymethylene)phenyl]acetamide ~ CH(OCH3)-C(=O)-NHCH3 ~ CHzO
3.9 g of a 40 percent strength aqeous methylamine solution were added to a mixture of 1.5 g of the product from 1.2 and 15 ml of tetrahydrofuran at 25 C. After 6 hours at 70 C, the reaction 30 mixture was freed from the solvent at reduced prQssure. The residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 1.2 g of the target compound were obtained (mp. 70 - 71 C).
35 F~mple 6 Methyl a-ethylamino-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~ H~NHCzHs)-C(=O)-OCH3 524 ~99~2~
1.1 g of a 70 percent strength a~ueous methylamine solution were added to a mixture of 1.9 g of the product from 4.1 and 20 ml of tetrahydrofuran at 25 C. After 2 hours at 50 C, the reaction mixture was freed from the solvent at reduced pressure. The 5 residue was taken up in tert-butyl methyl ether. After purifying the organic phase with water, drying and evaporating down, 1.7 g of the target compound were obtained tIR (cm~l: 1738, 1496, 1462, 1453, 1435, 1240, 1206, 1161, 1122, 7511.
10 Example 7 Methyl a-methoxyamino-a-~2-(2-methylphenoxymethylene)phenyl]acetate ~,,CH(NHoCH3j-Co2cH3 2.4 g of sodium hydroxide were added to a mixture of 5 g of methoxyamine hydrochloride and 50 ml of water at 5 C. After 10 minutes, a mixture of 4.2 g of the product from 4.1 and 50 ml of 25 tetrahydrofuran was added to this mixture at 5 C. After 2 hours at 50-C, a mixture of 5 g of methoxyamine hydrochloride, 50 ml of water and 2.4 g of sodium hydroxide was added to the reaction mixture. After 24 hours at 70 C, the reaction mixture was freed from the solvent at reduced pressure. The residue was taken up in 30 tert-butyl methyl ether. After purifying the organic phase with water, drying, evaporating down and flash chromatography t5:1 cyclohexane/tert-butyl methyl ether], 2.5 g of the target cu.,l~ound were obtained (mp. 60-62 C).
35 Example 8 Methyl a-methoxyamino-a- -~2-(2-methylphenoxymethylene)phenyl]acetate ~" CH(SCH3)-CO2cH3 ~ g3~2~
A mixture of 1.9 g of the product from 4.1, 0.43 g of sodium thiomethylate and 20 ml of dimethylformamide were stirred for 4 hours at 25 C. The reaction mixture was then freed from the solvent at reduced pressure. The residue was taken up in 5 tert-butyl methyl ether. After purifying the organic phase with water, drying, evaporating down and flash chromatography [5:1 cyclohexane/tert-butyl methyl ether], 0.6 g of the target compound was obtained (mp. 64-66 C).
o Table N
,~ CH ( UR ' )--COVR' ' ~
Xn~l~ Y ~--A ' ( I ' ) No. UR' VRn XnY' A' Physical data OCH3 OCH3 HCH2O 2-CH3-C6H4 1753, 1496, 1461, 1453, 1436, 1241, 1193, 1121, 1013, 751 2 OCH3 OCH3 HCH2O 2,5~CH3)2-C6H3 1753, 1509, 1453, 1261,ll9S, 1172, 1155, ~"
1129, 1116, 1017 3 OCH3 OCH3 HCH2O 2~4~cH3)2 C6H3 1753, 1504, 1253, l~l, 1196, 1172, 1133, 1116, 1013, 751 4 OCH3 OCH3 HCH2O 2-CH3~-CH(CH3)2-C6H3 1754, 1512, 1455, 1251, 1195, 1178, 1117, S OCH3 OCH3 HCH20 2-CH3-4-[C(CH3)=NOCH33-C6H3(E3 76- 78 6 OCH3 OCH3 HCH2O 2-CH3-4-[C(CH3)=NOC2H5]-C6H3(E) 1753, 1506, 1277, 1242, 1193, 1143, 1094, 1051, 1012 7 OCH3 OCH3 ' HCH2O 2~s-(cH3)2-4-[c(cH3)=Noc2H53-c6H2(E) 1753, 1510, 1327, 1245,ll9S, 1147, 1117, 2 1092, 1046, 1011 No. UR' -VR" XnY' A' Physicaldata o 8 OCH3 OCH3 HCH2O 2-n-C3H7-6-CF3-pyrimidin-4-yl 1755, 1599, 1572, 1421, 1352, 1185, 1151, ~
1121, 1091, 1017 9 OCH3 OCH3 HCH2O l-C6Hs-pyrazol-3-yl 1751, 1600, 1545, 1507, 1480, 1464, 1358, 1195, 1115, ?55 OCH3 OCH3 HCH2O 1~4-CH3-C6H4)-pyrazol-3-yl 1752, 1544, 1519, 1483, 1453, 1359, 1195, 1115, 1097, 746 11 OCH3 OCH3 HCH2O 1~4-CI-C6H4)-pyrazol-3-yl 1752, 1546, 1503, 1481, 1358, 1195, 1115, 1094, 936, 749 12 OCH3 OCH3 HCH2O 1~2,~CI2-C6H3)-pyrazol-3-yl 1753, 1547, 1496, 1474, 1357, 1195; 1110, 1057, 1020, 747 13 OCH3 OCH3 HCH2O (4-CI-C6H4)-C(CH3)=N(E) 1753, 1491, 1195, 1172, 1114, 1097, 1013, u 929, 830, 755 14 OCH3 OCH3 HCH2O (3,5-CI2-C6H3) C(CH3)=N(E) 1753, 1558, 1304, 1195, 1172, 1115, 1098, 1016, 995, 801 OCH3 OCH3 HCH2O (3-CF3-C6H4)-C(CH3)=N(E) 1753, 1341, 1298, 1276, 1195, 1168, 1124, 1100, 1072, 1016 16 OCH3 OCH3 HCH2O (4-CF3-C6H43-C(CH3)=N(E) 1753, 1328, 1195, 1169, 1116, 1099, 1065, 1014, 844, 745 17 OCH3 OCH3 HCH2O (4-cH3-c6H4)-c(cH3)=N(E) 1753, 1452, 1368, 1195, 1172, 1115, 1099, 1015, 926, 818 18 OCH3 OCH3 HCH20 (3-CI-C6H4)-C(CH3)=N (E) 1752, 1195, li72, 1115, 1098, 1015, 998, 786, 756, 688 ~
NO. UR' VR" XDY' A' Physical data ~n 19 OCH3 OCH3 HCH2O CH3 1752, 1452, 1436, 1195, 1172, 1113, 1102, ~
1013, 752 n OCH3 OCH3 H _ CH2Br 1752, 1435, 1273, 1215, 1195, 1171, 1109, n 1012, 762 21 OCH3 OCH3 HCH2O 1~5-CF3-pyrid-2-yl)-pyrazol-3-yl 1754, 1609, 1553, 1501, 1431, 1358, 1326, 1164, 1126, 1089 22 OCH3 OCH3 HCH20 1-(5-CF3-pyrid-2-yl)~CI-pyrazol-3-yl 84- 85 23 OCH3 OCH3 HCH20 4~4-CI-C6H4)-thi~ol-2-yl 82- 83 24 OCH3 OCH3 H CH2 4~4-CI-C6H4)-thiazolin-2-on-3-yl 145-150 OCH3 OCH3 HCHzO 4~2,~CIz-C6H3)-thiazol-2-yl 1753, 1530, 1465, 1305, 1253, l~s, 1195, u 1173, 1110,751 26 OCH3 OCH3 H CH2 4~2,4-CI2-C6H3tthi~7nli~ 2-on-3-yl 1751, 1662, 1602, 1471, 1453, 1435, 1215, 1195, 1176, 1102 27 OCH3 OCH3 HCH2O 3-CH3~[C(CH3)=NOC2Hs]-C6H3(E) 1753, 1605, 1503, 1240, 1195, 1170, 1116, 1092, 1048, 1014 28 OCH3 OCH3 HCH2O 2-CI-5-CH3~lC(C2H5)=NO-n-C3H~l-C6H2 1753, 1499, 1251, 1196, 1171, 1116, 1105, 1052, 1019 29 OCH3 OCH3 HCH20 2,5-CI2-4-[C(C2Hs)=NOC2Hs]-C6H2 (E) 1753, 1487, 1252, 1230, 1196, 1116, 1082, 1051, 1008, 750 ~:' No. UR' VR" XnY' A' Physical data o 30 OCH3 OCH3 HCH2O H3CON=C(CH3)C(CH3)=N (E);(E) 1.99(3H,s); 2.Q4(3H,s);3.39(3H,s); ~
3.72(3H,s); 3.92(3H,s); 5.17(1H,s); - u~
5.32(2H,AB); 7.3-7.55(4H,m) O
31 OCH3 OCH3 HCH2O Hsc2oN=c(cH3)c(cH3)=N (E)j(E) 1.29(3H,t); 1.99(3H,s); 2.04(3H,s);
3.39(3H,s); 3.72(3H,s);3.92(3H,s); 4.19 (2H,q); 5.20(1H,s);5.32(2H,AB);
7.3-7.55(4H,m)-32 OCH3 OCH3 HCH2O H3CON=C(C6Hs)C(CH3)=N(E);(E) 1753, 1212, 1196, 1173, 1116, 1097, 1058, 1035, 1011, 694 33 OCH3 OCH3 HCHzO Hsc2oN=c(c6Hs)c(cH3)=N(E);(E) 1753, 1210, 1196, 1171, 1116, 1093, 1056, 1036, 1011, 926 34 OCH3 OCH3 HCH2O O=C(CH3)C(CH3)=N (E) 1753, 1694, 1360, 1309, 1196, 1173, 1117, 1098, 1020, 750 35 OCH3 OCH3 HCH2O O=C(C6Hs)C(CH3)=N(E) 1753, 1661, 1325, 1192, 1176, lllS, 1098, 1004, 996, 711 36OCH2CH3 OCH2CH3 HCH2O 2-CH3-C6H4 1749, 1495, 1463, 1240, 1194, 1174, 1121, 1030, 751 37OCH2CH3 OCH3 HCH2O 2-CH3-C6H4 1752, 1496, 1454, 1436, 1240, 1196, 1171, 1121, 1013, 751 38 OCH3 OCH3 HCH2O 2-CI-S-CH3-C6H3 1752, 1490, 1285, 1255, 1215, 1195, 1177, 1116, 1062, 1015 c~
No. UR' V~" XaY' A' Physical data o 39OCH2CH3 OCH3 H _ CH2Br 1753, 1456, 1435, 1271, 1211, 1169, 1139, 1110, 761 u~
40OCH2CH3 OCH2CH3 HCH2O 2,5~CH3)~C6H3 1750, 1509, 1262, 1195, 1174, 1156, 1129, ~
1114, 1023 41OCH2CH3 OCH3 H CHp 2-CH3-4-lC(CH3)=NOCH3] C6H3(E) 1.26(3H,t);2.21(3H,s); 2.27(3H,s);
3.55(2H,q); 3.73(3H,s); 3.98(3H,s);
5.20(1H,s); 5.25(2H,AB); 6.9-7.6(7H,m) 42OCH2CH3 OCH3 HCHzO 2,5~CH3kC6H3 1.27(3H,t), 2.21(3H,s); 2.35(3H,s);
3.55(2H,q); 3.73(3H,s); 5.21(1H,s);
5.25(2H,AB); 6.7-7.6(7H,m).
43 OCH3 OCH3 HCH20 n-H7C30N=C(CH3)c~(CH3)=N (E);(E) 0.95(3H,t); 1.70(2H,m); 2.00(3H,s);
2.05(3H,s); 3.39(3H,s); 3.70~3H,s);
4.09(2H,t); 5.22(1H,s); 5.34(2H,AB); ~
7.25-7.55(4H,m) 44 OCH3 OCH3 HCH20 n-HgC4ON=C(CH3)C(CH3)=N(E);(E) 0.95(3H,t); 1.37(2H,m); 1.66(2H,m);
2.00(3H,s); 2.05(3H,s); 3.39(3H,s);
3.71(3H,s); 4.14(2H,t); 5.20(1H,s);
5.34~2H,AB); 7.25-7.55(4H,m) 45 OCH3 OCH3 HCH20 n-H7C3ON=C(C6Hs)C(CH3)=N (E);~E) 1753, 1209, 1196, 1172, 1116, 1097, 1067, 1013, 989 46 OCH3 OCH3 HCH2O n-HgC4ON=C(C6Hs)C(CH3)=N (E);(E) 1753, 1196, 1172, 1116, 1097, 1071, 1013, ~3 NO. UR' VRn XD Y' A' Physicaldata o 48 OCH3 NHCH3 H CHzO ~S-(CH3)2-C6H3 62-64 49 NHCH3 OCH3 H CH2O 2-CH3-C6H4 1738,1496,1452,1435,1240,1191,1170, 1122,1002,752 ~
50 NHCH3 OCH3 H CHzO 2,5~CH3)2-C~H3 1738,1509,1452,1262,1208,1170,1155, 1129,1020,755 51NHCH2CH3 OCH3 H CH2O 2-CH3-C6H4 1738,1496,1462,1453,1240,1206,1161, 1122,751 52NHCH2CH3 OCH3 H CH2O 2,5~CH3)2-C6H3 1738,1509,1453,1434,1262,1206,1155, 1129,1021,755 53NH(II-C3H7) OCH3 H CHZO 2~CH3~4H.I 1738, 1496, 1461, 1435, 1241, 1197, 1162, 54NH(n-C3H7) OCH3 H CH2O 275-(CH3~2-C6H3 1739,1509,1457,1434,1262,1204,1155, 56NHOCH3 OCH3 H CH2O 2,5~CH3)2-C6H3 91-92 57 NHCH3 NHCH3 H CH20 2,5~CH3k~C6H3 2.17(3H,s);2.32(3H,s);2.37~3H,s);
2.80(3H,d);4.40~1H,s);5.19(2H,AB);
6.7-7.5(8H,m) 58NHCH2CH3 NHCH3 H CH2O 2-CH3-C6H4 1.08(3H,t);2.23(3H,s);2.63(2H,q);
2.80(3H,d);4.. 48(1H,s);5.22(2H,AB); ~3 6.85-7.5(9H,m).
No. UR' VR" XnY' A' Physicaldata o 59 NHCH3 NHCH3 HCH20 2-CH3-C6H4 72- 74 ,p 60 OCH3 NHCH3 HCH2O H3CON=C(CH3)C(CH3)=N(E)j(E) 1661, 1550,1362, 1088, 1060,995,981, ul 899, 888 ~
61 OCH3 NHCH3 HCH20 HsCzON=C(CH3)C(CH3)=N (E);(E) 1660, 1094, 1005, 995, 979, 947, 904, 891, 62OCH2CH3 NHCH3 HCH2O 2-CH3-C6H4 1664, 1533, 1499, 1480, 1408, 1238, 1119, 757, 749 63 OCH3 NHCH3 HCH2O 2-CI-5-CH3-C6H3 1671, 1532, 1490, 1410, 1285, 1254, 1176, 1113, 1095, 1062 64 OCH3 NHCH3 HCH2O O=c(cH3)c(cH3)=N (E) 1693, 1674, 1532, 1360, 1126, 1114, 1096, 1022, 992, 750 65OCH2CH3 NHCH3 HCH20 2-CH3~-~C(CH3)=NOCH31-C6H3 (E) 1.27(3H,t); 2.20(3H,s); 2.25(3H,s);
2.83(3H,d); 3.51(2H,m); 3.98(3H,s);
5.11(1H,s); 5.35(2H,AB);6.87(1H,d);
6.9-7.55(7H,m) 66OCH2CH3 NHCH3 HCH20 2~5~cH3)2-c6H3 1.24(3H,t); ~20(3H,s); 2.34(3H,s);
2.84(3H,d); 3.52(2H,m); 5.14(1H,s);
- 5.28(2H,AB);6.87(1H,d); 6.65-7.6(7H,m) 67 OCH3 NHCH3 HCH2O n-H7C3ON=C(C6Hs)C(CH3)=N (E);(E) 1672, 1531, 1113, 1095, 1068, 988, 749, 68 OCH3 NHCH3 H CHp rl-HgC4oN=c(c6Hs)c(cH3)=N(E);(E) 1673, 1531, 1113, 1096, 1028, 1012,993, ~'3 No. UR' VR~ Xn Y' A' Physi~lda~ o 69 SCH3 NHCH3 H CH20 2-CH3-C6H4 64-66 ~
OCH3 NHCH3 H CH2O n-H7C3ON=C(CH3)C(CH3)=N(E);(E) 1669,1532,1365,1113,1096,1018,990, 71 OCH3 NHCH3 H CH2O n-H9c4oN=c(cH3)c(cH3)=N(E);O 1668,1532,1365,1096,1027,1017,992, 72 OCH3 NHCH3 H CH2O H3CON=C~C6Hs)C(CH3)=N(E);~E) 1671,1532,1113,1095,1059,1034,993, 73 OCH3 NHCH3 H CH2O Hsc2oN=c(c6Hs)c(cH3)=N(E);(E) 1672,1532,1113,1094,1057,1035,1006, 74 OCH3 NHCH3 H CH2O 2-CH3-4-lC(CH3)=NOCH3l-C6H3(E) 2.18(3H,s);2.26(3H,s);2.81(3H,d);
3.34(3H,s);3.97(3H,s);5.00(1H,s);
5.31(2H,AB);6.83(1H,d);6.9-7.5(7H,m) OCH3 NHCH3 H CH2O 1-(2,4-CI2-C6H3)-pyr~ol-3-yl 2.82(3H,d);3.35(3H,s);5.10(1H,s);
5.55(2H~UB);5.93(1H,d);6.85(1H,d);
7.3-7.8(8H,m) 76 OCH3 NHCH3 H CH2O 1~4-CI-C6H4)-pyr~ol-3-yl 2.85(3H,d);3.38(3H,s);5.10(1H,s);
5.55(2H~B);5.93(1H,d);6.85(1H,d);
7.3-7.7(9H,m) 77 OCH3 NHCH3 H CH2O 2,5~CH3)2-C6H3 98-100 78 OCH3 OCH3 H CH20 2,5~CH3)2-4-[C(CH3)=NOCH3l-C6Hz(E) 1753,1510,1326,1245,1195,1146,1115, 1044,1011,876 c~
No. UR' VR" XOY' A' Physicaldata o 79 OCH3 NHCH3 HCH20 2,5~CH3)2-4-[C(CH3)=NOCH3]-C6Hz (E) 1671, 1532, 1510, 1326, 1244, 1147, 1095, ~
1044, 876 OCH3 NHCH3 HCH2O 2-CH3-4-lC(CH3)=NOC2Hsl-C6H3(E) 1672, 1532, 1506, 1319, 1244, 1143, 1112, "
1093, 1051 81 OCH3 NHCH3 HCH20 2,5~CH3)2-4-~C(CH3)=NOC2Hs¦-C~H2 (E) 1672, 1531, 1511, 1327, 1244, 1147, 1112, 1093, 1047 82 OCH3 NHCH3 HCH2O l-C6Hs-pyrazol-3-yl 1617, 1600, 1545, 1507, 1479, 1464, 1399, 1358, 1095 83 OCH3 NHCH3 HCH20 1~4-CH3-C6H4)-pyrazol-3-yl 109-112 84 OCH3 OCH3 HCH2O 1~4-CI-C6H4~1,2,4-tdazol-3-yl 1751, 1545, 1501, 1481, 1329, 1196, 1115, ~ 1094, 981, 972 OCH3 NHCH3 HCH20 1~4-CI-C6H4)-1,2,4-triazol-3-yl 115-116 86 OCH3 OCH3 H CHp 1~2,4-CI-C6H3)-1,2,4-triazol-3-yl 17S1, 1545, 1493, 1476, 1330, 1195, 1109, 1061, 971 87 OCH3 NHCH3 HCH20 1~2,~CI-C6H3~-1,2,4-triazol-3-yl 104-105 88 OCH3 NHCH3 HCH2O (4-CF3-C6H4)-C(CH3)=N (E) 1670, 1534, 1408, 1328, 1167, 1115, 1096, 1065, 1015, 844 89 OCH3 NHCH3 HCH2O (4-CH3-C6H4)-C(CH3)=N(E) 1670, 1532, 1452, 1112, 1097, 1018, 991, 925, 818 go OCH3 NHCH3 HCH20 (3,5-CI2-C6H3)-C(CH3)=N (E) 81- 83 t'3 No. UR' VR" XnY' A' Physical data o 91 OCH3 NHCH3 HCH2O (4-CI-C6H4)-C(CH3)=N (E) 1670, 1532, 1491, 1111, 1096, 1012, 993, ~
929,830 ~
92 OCH3 NHCH3 HCH2O (3-CI-C6H4)-C(CH3)=N(E) 1670, 1559, 1532, 1410, 1112, 1096, 992, ~
93 OCH3 NHCH3 HCH20 (3-CF3-C6H4)-C(CH3)=N (E) 58- 61 94 OCH3 OCH3 HCH2O (4-OC2Hs-pJ.i~ 2-yl)-C(CH3)=N (E) 1753, 1570, 1557, 1447, 1324, 1195, 1115, 1096, 1032, 986 95 OCH3 NHCH3 HCH2O (4-OC2H5-p~,il,,;dil~-2-yl)-C(CH3)-N (E) 77- 78 96 OCH3 OCH3 HCH2O (4-OCH2CF3-~ l"~ -2-yl)-C(CH3)=N(E) 1753, 1568, 1442, 1333, 1263, l~o, 1170, 1116, 1061, 1016 97 OCH3 NHCH3 HCH20 (4-OCH2C~3-l",illlillill-2-yltC(CH3)=N (E) 114-116 98OCH2CH3 OCH3 HCH2O 1~4'-CI-C6H4)-pyrazol-3-yl 1751, 1546, 1503, 1481, 1358, 1113, 1094, 936, 828 99OCH2CH3 OCH3 HCH2O (4-cl-C6H4)-C(CH3)=N(E) 1752, 1491, 1368, 1206, 1171, 1112, 1096, 1012, 928, 830 100OCH2CH3 OCH3 HCH2O (3,5-C12-C6H3)-C(CH3)=N(E) 1753, 1558, 1305, 1204, 1170, 1114, 1098, 1018, 994, 801 101OCH2CH3 OCH3 HCH2O H3CON=C(C6H5)C(CH3)=N (E) 1752, 1445, 1209, 1172, 1114, 1056, 1035, 1005, 994 102OCH2CH3 OCH3 HCH20 H3CON=C(CH3)C(CH3)=N (E) 50 C~
No. UR' VR" XnY' A' Physical data ~
103OCH3 NHCH3 H ~ C6Hs 1669, 1583, 1532, 1486, 1453, 1234, 1204, ~
1191, 1093 104OCH2CH3 NHCH3 H ~ C6Hs 1669, 1583, 1531, 1486, 1453, 1234, 1104, ~
1088, 753 105OCH3 OCH3 H ~ C6H5 1751, 1583, 1486, 1453, 1236, 1196, 1165, 1111, 1092, 753 106OCH2CH3 OCH3 H O C6Hs 1752, tS84, 1487, 1454, 1237, 1205, 1166, 1112, 1091, 753 109OCH3 OCH3 HCH2O 1~4-F-C6H4)-pyrazol-3-yl 1751, 1545, 1516, 1484, 1359, 1221, 1195, w 1115, 834, 746 110OCH3 NHCH3 HCH2O 1~4-F-C6H4)-pyrazol-3-yl 1669, 1545, 1516, 1483, 1462, 1436, 1290, 1271, 1230, 747 111OCH2CH3 NHCH3 HCH2O 1~4-CI-C6H4)-pyrazol-3-yl 97- 98 i 112OCH2CH3 NHCH3 HCH20 (4-CI-C6H4)-C(CH3)=N (E) 82- 83 113OCH2CH3 NHCH3 HCH2O (3,5-CI2-C6H3)-C(CH3)=N (E) 96- 97 114OCH2CH3 NHCH3 HCH20 H3CON=C(C6Hs)C(CH3)=N (E);(E) 90- 91 115OCH2CH3 NHCH3 HCH20 H3CON=(~(CH3)C(cH3)=N (E);(E) 59- 64 No. UR' VR" XnY' A' Physical data o 116 OCH3 OCH3 H O H 81-83 ~
117 OCH3 OCH3 H _ CHO 1749, 1697, 1598, 1436, 1200, 1113, 1011, N
758 o 118 OCH3 OCH3 H CH2 P(=O)~OCH3)2 1752, 1253, 1195, 1110, 1055, 1030, 855, 835, 795 119 OCH3 OCH3 H CH2 P~C6Hs)3 B~ 217-219 120 OCH3 OCH3 HCH20 5,7~CH3)2-pyrazolo[1,5a3-pyrimidin-2-yl 84- 86 121 OCH3 OCH3 HCH2O 5,7-(CH3)2-3-C2Hs-pyla- 1753, 1630, 1585, 1535, 1507, 1451, 1370, zolol1,5al-pyrimidin-2-yl 1196, 1166, 1116 122 OCH3 NHCH3 HCH20 5,7~CH3)2-~ la,1,5a]-1",i,.. iJi-l-2-yl 89- 93 w 123 OCH3 NHCH3 HCHzO 5,7~CH3)2-3-C2Hs-pyra- 134-136 zolo~l,Sal-~ - 2-yl 124 OCH3 OCH3 HCH2O 2-CH3-5-CH=NOCH3-C6H3 (E) 80- 81 125 OCH3 NHCH3 HCH20 2-CH3-5-CH=NOCH3-C6H3 (E) 89- 91 126 OCH3 OCH3 HCH2O 2-CH3-S-CH=NOC2Hs-C6H3 O 65- 67 127 OCH3 NHCH3 HCH2O 2-CH3-5-CH=NOC2H5-C6H3(E) 86-88 128 OCH3 OCH3 HCH2O 2-CH3-5-CHO-C6H3 1752, 1693, 1422, 1254, 1197, 1118, 1015, C~
No. UR' VR" XnY' A' Physical data o 130 OCH3 OCH3 H O 6-1(2-CN C6H4)-O]-p~iulidi-~-4-yl 95-97 131 OCH3 OCH3 H O 6-l(2-CI-C6H4)-Ol-pyrimidin-4-yl 74- 76 o 132 OCH3 OCH3 H O 6-l(2-F-C6H4)-O~ ;Ji-1-4-yl 1753, 1604, 1592, 1576, 1499, 1451, 1261, 1217, 1189, 1143 133 OCH3 OCH3 H O 6-l(2-Br-C6H4)-O]-~J~ ;Jill-4-yl 71- 73 134 OCH3 OCH3 H O 6-l(2,6-F2-C6H3)-O]-pyrimidin 4-yl 1753, 1596, 1573, 1500, 1451, 1260, 1217, 1200, 1176, 1146 135 OCH3 OCH3 H O 6-l(2-NO2-C6H4)-O]-pyrimidin~l yl 103-105 136 OCH3 OCH3 H O 6-[(2-CH3-C6H4)-O]_p~ilniJill_4_yl 1754, 1596, 1573, 1488, 1450, 1248, 1219, 1179, 1148, 1111 137 OCH3 OCH3 H O ~l(2-CH3O-C6H4)-Ol-pyrimidin-4-yl 1754, 1595, 1573, 1501, 1480, 1451, 1246, 1212, 1142, 1013 13P,OCH3 OCH3 H O 6-CI-~,illlill;l~ 4 yl 1754, 1559, 1444, 1351, 1258, 1213, 1088, 139 OCH3 OCH3 HCH20 2-CH3-5-lC(CH3)=NOCH3]-C6H3 (E) 1753, 1412, 1319, 1235, 1196, 1116, 1098, 1051, 1015, 874 140 OCH3 NHCH3 HCHzO 2-CH3-5-lC(CH3)=NOCH31-C6H3 (E) 96- 98 141 OCH3 OCH3 HCH2O 2-CH3-S-lC(CH3)=NOC2H5l-C6H3(E) 1754, 1413, 1318, 123S, 1195, 1170, 1116, 1093, 1050, 1014 142 OCH3 NHCH3 HCH20 2-CH3-S-[C(CH3)=NOC2Hs]-C6H3(E) 74- 76 c~
NO. UR' VR" XD Y- A' Physicaldata o 143 OCH3 OCH3 HCHzO 2-CH3-S-C(=O)CH3-C6H3 1752,1680,1414,1268,1193,1115,1013 ~
144 OCH3 NHCH3 HCH20 2-CH3-S-C(=O)CH3-C6H3 97- 99 ~n 145 OCH3 NHCH3 H O 6-[(2-CN-C6H4)-Ol-p,~ yl 1677,159S, 1581,1568,1487,1445,1248, 1~8, 1144 146 OCH3 NHCH3 H O 6-[(2-F-C6H4)-OI-pyrimidin-4-yl 1675,1606,1592,1576,1499,1450,1261, 1216, 1189, 1143 147 OCH3 NHCH3 H O 6-[(2-CI-C6H4)-O]-~ id;.~ 4 yl 1675,1599,1573,1477,1447,1383,1262, 1248, 1217, 1145 148 OCH3 NHCH3 H O 6-~(2-Br-C6H4)-O]-~ lill-4-yl 1676,1599, 1571,1451,1442,1381,1261, 1247, 1217, 1146 149 OCH3 NHCH3 H O 6-~(2,6-F2-C6H3)-O~ ll-4-yl 1675,1595,1574,1501,1479,1452,1246, ~O
1211, 1141, 1012 150 OCH3 NHCH3 H O 6-~(2-NO2-C6H4)-O]-p~.illlidin-4-yl 1675,1593,1576,1529,1450,1384,1349, 1248, 1215, 1146 151 OCH3 NHCH3 H O 6-l(2-CH3O-C6H4)-Ol 1,~.inlidin-4-yl 1676,1608,1596,1572,1500,1450, lZ60, 1199, 1175, 1147 152 OCH3 OCH3 H O 6-CI-pyrimidin-4-yl 137-139 153 OCH3 OCH3 HCH2O 2-CH3, 4-l-C6H3 86- 88 154 OCH3 NHCH3 HCHzO 2-CH3, 4-l-C6H3 1671,1531,1488,1453,1242,1188,1134, 1112, 1094, 751 c~
~' No. UR' VR~ X~ Y' A' Physi~lda~ o 155 OCH3 OCH3 H CH2O 2-CH3,5-l-C6H3 56-58 ~
156 OCH3 NHCH3 H CH2O 2-CH3,5-I-C6H3 105-106 157 OCH3 NHCH3 H CH2O 2-CH3,4~4-CH3-C6H4)-C6H3 64-67 158 OCH3 NHCH3 H CH2O 2-CH3,5~4-CH3-C6H4)-C6H3 93-94 159 OCH3 OCH3 H CH2O 3-(3-CH3-C6H4)-C6H4 1752,1602,1576,1215,1194,1181,1167, 1115,1015, m 160 OCH3 NHCH3 H CH2O 3~3-CH3-C6H4)-C6H4 1673,1603,1576,1531,1474,1215,1181, 1111,1095,777 161 OCH3 OCH3 H CH2O 2~4-CI-C6H4)-pyrimid~-4-yl 95-97 162 OCH3 NHCH3 H - CH2O 2~4-CI-C6H4)-p~lilli.li.l~ yl 97-103 O
163 oCH3 OCH3 2,3-lCH=C(C6H5)-CH=CH*] 72-74 164 OCH3 NHCH3 2,3-lCH=C(C6H5)-CH=CH*] 94-97 165 OCH3 OCH3 2,3-[CH=C(4-CI-C6H4)-CH=CH*l 63-66 166 OCH3 NHCH3 2,3-lCH=C(4-CI-C6H4)-CH=CH*] 59-64 167 OCH3 OCH3 2,3-[CH=CBr-CH=CH*] 63-66 168 OCH3 NHCH3 2,3-~CH=CBr-CH=CH*] 63-66 169 OCH3 OCH3 H CH2ON=C(CH3)-C~4-~-C6H4]=NOCH3(E;E) 1753,1508,1221,1197,1160,1116,1098, 1067,1008,841 ~
,4' ~3 i~
No. UR' vRn XnY' A' Physicaldata o 170 OCH3 NHCH3 HCH2O N=C(CH3)-CI4-F-C6H41=NOCH3 (E;E) 93-94 ~
171 OCH3 OCH3 HCH2O N=C(CH3)-C[4-F-C6H4l=NOCH2CH3 (EjE) 1754, 1508, 1221, 1196, 1116, 1096, 1036, ul 1010,975,956 ~
172 OCH3 NHCH3 HCHzO N=C(CH3)-C[4-F-C6H4]=NOCHzCH3 (EjE) 86- 88 173 OCH3 OCH3 2,3-[O-C(C6Hs)=CH~] 104-105 174 OCH3 NHCH3 2,3-[O-C(C6Hs)=CH*I 130-132 175 OCH3 OCH3 HCH2=N CH2-[3-CF3-C6H4] 1752, 1330, 1200, 1167, 1123, 1100, 1074, O 1015, 759 176 OCH3 OCH3 H _ Br 1752, 1436, 1213, 1195, 1179, 1122, 1107, 1026, 1012, 754 177 OCH3 NHCH3 H - Br 3329, 1667, 1533, 1470, 1439, 1408, 1196, 1100, 1026, 753 #: Mp. (~C), lH-NMR (ppm); IR (cm-l) ~: Bond to posi~ion 3 of the phenyl radical c~
~ f~
~ ~g~2~
Examples of the action again harmful fungi The fungicidal action of the compounds of the formula I could be 5 demonstrated by the following experiments:
The active ingredients were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil~ LN (Lutensol~ AP6, wetting agent having an emulsifying 10 and dispersing action and based on ethoxylated alkylphenols) and 10~ by weight of Emulphor~ EL (Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with water to give the desired concentration.
15 Erysiphe gr~m;n~S var. tritici (wheat mildew) Leaves of wheat seedlings (FrUhgold variety) were first treated with the agueous formulation of the active ingredient. After about 24 hours, the plants were dusted with spores of wheat 20 mildew (Erysiphe graminis var. tritici). The plants thus treated were then incubated for 7 days at 20-22'C and a relative humidity of 75-80%. The extent of fungal development was then determined.
In this test, the plants treated with an active ingredient 25 formulation cont~;n~ng 63 ppm (co,.~ound~ No. 1, 2, 3, 4, 5, 6, 7, 13, 14, lS, 16, 17 and 18) exh ~ h1 ted an infestation of 5% or less, whereas the untreated plants (control experiment) exhibited 65% infe~tation.
30 In a corresponding test, the plants treated with active ingredient formulation cont~;n~ng 63 ppm (cv...pounds No. 27-31, 38, 43, 47, 48, 55, 56, 60, 61, 63, 70, 74, 81, 88, 93 and 102) exhibited an infestation of 5~ or less, whereas the untreated plants (control experiment) exhibited 65% infestation.
Pyricularia oryzae rrice blastJ
Rice seedlings (Tai Nong 67 variety) were sprayed to run-off with the active ingredient formulation. After 24 hours, the plants 40 were sprayed with an aqueou~ spore suspension of the fungu~
Pyricularia oryzae and kept for 6 days at 22-24 C and a relative humidity of 95-99%. The evaluation wa~ carried out visually.
In this test, the plants treated with active ingredient 45 formulation cont~;n;ng 250 ppm (cv.~ unds No. 2, 3, 4, 5, 6, 7, 13, 14, 15, 16, 17, 18 and 21) exhibited an infestation of 15~ or 543 2~4~
less, whereas the untreated plants (control experiment) exhibited 70% infestation.
In a corresponding test, the plants treated with active 5 ingredient formulation containing 250 ppm (c~l..~ounds No. 27, 28, 30-32, 35, 38, 40, 41, 43-45, 48, 50, 53-56, 61, 63, 65, 67-69, 72, 74, 76-85, 87-91, 93, 94, g7, 100, 102, 110 and 112) exhibited an infestation of 15% or less, whereas the untreated plants (control experiment) exhibited 70% infestation.
Examples of action against ~ni~l pests The action of the co.~pounds of the general formula I against An; ~l pests could be demonstrated by the following experiments:
The active ingredients were prepared a) as a 0.1% strength solution in acetone or b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil~ LN ~Lutensol~ AP6, wetting agent having an emulsifying and dispersing action and based on ethoxylated alkylphenols) and 10~ by weight of Emulphor~ EL (Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with acetone in the case of a) and with water in the case of b) to give the desired concentration.
After the end of the experiments, the lowest concentration in 30 each case at which the ~o..~ounds still caused 80-100% inhibition or mortality in compArison to untreated control experiments (action threshold or m; n; m~l~ concentration) was determined.
3.39(3H,s); 3.72(3H,s);3.92(3H,s); 4.19 (2H,q); 5.20(1H,s);5.32(2H,AB);
7.3-7.55(4H,m)-32 OCH3 OCH3 HCH2O H3CON=C(C6Hs)C(CH3)=N(E);(E) 1753, 1212, 1196, 1173, 1116, 1097, 1058, 1035, 1011, 694 33 OCH3 OCH3 HCHzO Hsc2oN=c(c6Hs)c(cH3)=N(E);(E) 1753, 1210, 1196, 1171, 1116, 1093, 1056, 1036, 1011, 926 34 OCH3 OCH3 HCH2O O=C(CH3)C(CH3)=N (E) 1753, 1694, 1360, 1309, 1196, 1173, 1117, 1098, 1020, 750 35 OCH3 OCH3 HCH2O O=C(C6Hs)C(CH3)=N(E) 1753, 1661, 1325, 1192, 1176, lllS, 1098, 1004, 996, 711 36OCH2CH3 OCH2CH3 HCH2O 2-CH3-C6H4 1749, 1495, 1463, 1240, 1194, 1174, 1121, 1030, 751 37OCH2CH3 OCH3 HCH2O 2-CH3-C6H4 1752, 1496, 1454, 1436, 1240, 1196, 1171, 1121, 1013, 751 38 OCH3 OCH3 HCH2O 2-CI-S-CH3-C6H3 1752, 1490, 1285, 1255, 1215, 1195, 1177, 1116, 1062, 1015 c~
No. UR' V~" XaY' A' Physical data o 39OCH2CH3 OCH3 H _ CH2Br 1753, 1456, 1435, 1271, 1211, 1169, 1139, 1110, 761 u~
40OCH2CH3 OCH2CH3 HCH2O 2,5~CH3)~C6H3 1750, 1509, 1262, 1195, 1174, 1156, 1129, ~
1114, 1023 41OCH2CH3 OCH3 H CHp 2-CH3-4-lC(CH3)=NOCH3] C6H3(E) 1.26(3H,t);2.21(3H,s); 2.27(3H,s);
3.55(2H,q); 3.73(3H,s); 3.98(3H,s);
5.20(1H,s); 5.25(2H,AB); 6.9-7.6(7H,m) 42OCH2CH3 OCH3 HCHzO 2,5~CH3kC6H3 1.27(3H,t), 2.21(3H,s); 2.35(3H,s);
3.55(2H,q); 3.73(3H,s); 5.21(1H,s);
5.25(2H,AB); 6.7-7.6(7H,m).
43 OCH3 OCH3 HCH20 n-H7C30N=C(CH3)c~(CH3)=N (E);(E) 0.95(3H,t); 1.70(2H,m); 2.00(3H,s);
2.05(3H,s); 3.39(3H,s); 3.70~3H,s);
4.09(2H,t); 5.22(1H,s); 5.34(2H,AB); ~
7.25-7.55(4H,m) 44 OCH3 OCH3 HCH20 n-HgC4ON=C(CH3)C(CH3)=N(E);(E) 0.95(3H,t); 1.37(2H,m); 1.66(2H,m);
2.00(3H,s); 2.05(3H,s); 3.39(3H,s);
3.71(3H,s); 4.14(2H,t); 5.20(1H,s);
5.34~2H,AB); 7.25-7.55(4H,m) 45 OCH3 OCH3 HCH20 n-H7C3ON=C(C6Hs)C(CH3)=N (E);~E) 1753, 1209, 1196, 1172, 1116, 1097, 1067, 1013, 989 46 OCH3 OCH3 HCH2O n-HgC4ON=C(C6Hs)C(CH3)=N (E);(E) 1753, 1196, 1172, 1116, 1097, 1071, 1013, ~3 NO. UR' VRn XD Y' A' Physicaldata o 48 OCH3 NHCH3 H CHzO ~S-(CH3)2-C6H3 62-64 49 NHCH3 OCH3 H CH2O 2-CH3-C6H4 1738,1496,1452,1435,1240,1191,1170, 1122,1002,752 ~
50 NHCH3 OCH3 H CHzO 2,5~CH3)2-C~H3 1738,1509,1452,1262,1208,1170,1155, 1129,1020,755 51NHCH2CH3 OCH3 H CH2O 2-CH3-C6H4 1738,1496,1462,1453,1240,1206,1161, 1122,751 52NHCH2CH3 OCH3 H CH2O 2,5~CH3)2-C6H3 1738,1509,1453,1434,1262,1206,1155, 1129,1021,755 53NH(II-C3H7) OCH3 H CHZO 2~CH3~4H.I 1738, 1496, 1461, 1435, 1241, 1197, 1162, 54NH(n-C3H7) OCH3 H CH2O 275-(CH3~2-C6H3 1739,1509,1457,1434,1262,1204,1155, 56NHOCH3 OCH3 H CH2O 2,5~CH3)2-C6H3 91-92 57 NHCH3 NHCH3 H CH20 2,5~CH3k~C6H3 2.17(3H,s);2.32(3H,s);2.37~3H,s);
2.80(3H,d);4.40~1H,s);5.19(2H,AB);
6.7-7.5(8H,m) 58NHCH2CH3 NHCH3 H CH2O 2-CH3-C6H4 1.08(3H,t);2.23(3H,s);2.63(2H,q);
2.80(3H,d);4.. 48(1H,s);5.22(2H,AB); ~3 6.85-7.5(9H,m).
No. UR' VR" XnY' A' Physicaldata o 59 NHCH3 NHCH3 HCH20 2-CH3-C6H4 72- 74 ,p 60 OCH3 NHCH3 HCH2O H3CON=C(CH3)C(CH3)=N(E)j(E) 1661, 1550,1362, 1088, 1060,995,981, ul 899, 888 ~
61 OCH3 NHCH3 HCH20 HsCzON=C(CH3)C(CH3)=N (E);(E) 1660, 1094, 1005, 995, 979, 947, 904, 891, 62OCH2CH3 NHCH3 HCH2O 2-CH3-C6H4 1664, 1533, 1499, 1480, 1408, 1238, 1119, 757, 749 63 OCH3 NHCH3 HCH2O 2-CI-5-CH3-C6H3 1671, 1532, 1490, 1410, 1285, 1254, 1176, 1113, 1095, 1062 64 OCH3 NHCH3 HCH2O O=c(cH3)c(cH3)=N (E) 1693, 1674, 1532, 1360, 1126, 1114, 1096, 1022, 992, 750 65OCH2CH3 NHCH3 HCH20 2-CH3~-~C(CH3)=NOCH31-C6H3 (E) 1.27(3H,t); 2.20(3H,s); 2.25(3H,s);
2.83(3H,d); 3.51(2H,m); 3.98(3H,s);
5.11(1H,s); 5.35(2H,AB);6.87(1H,d);
6.9-7.55(7H,m) 66OCH2CH3 NHCH3 HCH20 2~5~cH3)2-c6H3 1.24(3H,t); ~20(3H,s); 2.34(3H,s);
2.84(3H,d); 3.52(2H,m); 5.14(1H,s);
- 5.28(2H,AB);6.87(1H,d); 6.65-7.6(7H,m) 67 OCH3 NHCH3 HCH2O n-H7C3ON=C(C6Hs)C(CH3)=N (E);(E) 1672, 1531, 1113, 1095, 1068, 988, 749, 68 OCH3 NHCH3 H CHp rl-HgC4oN=c(c6Hs)c(cH3)=N(E);(E) 1673, 1531, 1113, 1096, 1028, 1012,993, ~'3 No. UR' VR~ Xn Y' A' Physi~lda~ o 69 SCH3 NHCH3 H CH20 2-CH3-C6H4 64-66 ~
OCH3 NHCH3 H CH2O n-H7C3ON=C(CH3)C(CH3)=N(E);(E) 1669,1532,1365,1113,1096,1018,990, 71 OCH3 NHCH3 H CH2O n-H9c4oN=c(cH3)c(cH3)=N(E);O 1668,1532,1365,1096,1027,1017,992, 72 OCH3 NHCH3 H CH2O H3CON=C~C6Hs)C(CH3)=N(E);~E) 1671,1532,1113,1095,1059,1034,993, 73 OCH3 NHCH3 H CH2O Hsc2oN=c(c6Hs)c(cH3)=N(E);(E) 1672,1532,1113,1094,1057,1035,1006, 74 OCH3 NHCH3 H CH2O 2-CH3-4-lC(CH3)=NOCH3l-C6H3(E) 2.18(3H,s);2.26(3H,s);2.81(3H,d);
3.34(3H,s);3.97(3H,s);5.00(1H,s);
5.31(2H,AB);6.83(1H,d);6.9-7.5(7H,m) OCH3 NHCH3 H CH2O 1-(2,4-CI2-C6H3)-pyr~ol-3-yl 2.82(3H,d);3.35(3H,s);5.10(1H,s);
5.55(2H~UB);5.93(1H,d);6.85(1H,d);
7.3-7.8(8H,m) 76 OCH3 NHCH3 H CH2O 1~4-CI-C6H4)-pyr~ol-3-yl 2.85(3H,d);3.38(3H,s);5.10(1H,s);
5.55(2H~B);5.93(1H,d);6.85(1H,d);
7.3-7.7(9H,m) 77 OCH3 NHCH3 H CH2O 2,5~CH3)2-C6H3 98-100 78 OCH3 OCH3 H CH20 2,5~CH3)2-4-[C(CH3)=NOCH3l-C6Hz(E) 1753,1510,1326,1245,1195,1146,1115, 1044,1011,876 c~
No. UR' VR" XOY' A' Physicaldata o 79 OCH3 NHCH3 HCH20 2,5~CH3)2-4-[C(CH3)=NOCH3]-C6Hz (E) 1671, 1532, 1510, 1326, 1244, 1147, 1095, ~
1044, 876 OCH3 NHCH3 HCH2O 2-CH3-4-lC(CH3)=NOC2Hsl-C6H3(E) 1672, 1532, 1506, 1319, 1244, 1143, 1112, "
1093, 1051 81 OCH3 NHCH3 HCH20 2,5~CH3)2-4-~C(CH3)=NOC2Hs¦-C~H2 (E) 1672, 1531, 1511, 1327, 1244, 1147, 1112, 1093, 1047 82 OCH3 NHCH3 HCH2O l-C6Hs-pyrazol-3-yl 1617, 1600, 1545, 1507, 1479, 1464, 1399, 1358, 1095 83 OCH3 NHCH3 HCH20 1~4-CH3-C6H4)-pyrazol-3-yl 109-112 84 OCH3 OCH3 HCH2O 1~4-CI-C6H4~1,2,4-tdazol-3-yl 1751, 1545, 1501, 1481, 1329, 1196, 1115, ~ 1094, 981, 972 OCH3 NHCH3 HCH20 1~4-CI-C6H4)-1,2,4-triazol-3-yl 115-116 86 OCH3 OCH3 H CHp 1~2,4-CI-C6H3)-1,2,4-triazol-3-yl 17S1, 1545, 1493, 1476, 1330, 1195, 1109, 1061, 971 87 OCH3 NHCH3 HCH20 1~2,~CI-C6H3~-1,2,4-triazol-3-yl 104-105 88 OCH3 NHCH3 HCH2O (4-CF3-C6H4)-C(CH3)=N (E) 1670, 1534, 1408, 1328, 1167, 1115, 1096, 1065, 1015, 844 89 OCH3 NHCH3 HCH2O (4-CH3-C6H4)-C(CH3)=N(E) 1670, 1532, 1452, 1112, 1097, 1018, 991, 925, 818 go OCH3 NHCH3 HCH20 (3,5-CI2-C6H3)-C(CH3)=N (E) 81- 83 t'3 No. UR' VR" XnY' A' Physical data o 91 OCH3 NHCH3 HCH2O (4-CI-C6H4)-C(CH3)=N (E) 1670, 1532, 1491, 1111, 1096, 1012, 993, ~
929,830 ~
92 OCH3 NHCH3 HCH2O (3-CI-C6H4)-C(CH3)=N(E) 1670, 1559, 1532, 1410, 1112, 1096, 992, ~
93 OCH3 NHCH3 HCH20 (3-CF3-C6H4)-C(CH3)=N (E) 58- 61 94 OCH3 OCH3 HCH2O (4-OC2Hs-pJ.i~ 2-yl)-C(CH3)=N (E) 1753, 1570, 1557, 1447, 1324, 1195, 1115, 1096, 1032, 986 95 OCH3 NHCH3 HCH2O (4-OC2H5-p~,il,,;dil~-2-yl)-C(CH3)-N (E) 77- 78 96 OCH3 OCH3 HCH2O (4-OCH2CF3-~ l"~ -2-yl)-C(CH3)=N(E) 1753, 1568, 1442, 1333, 1263, l~o, 1170, 1116, 1061, 1016 97 OCH3 NHCH3 HCH20 (4-OCH2C~3-l",illlillill-2-yltC(CH3)=N (E) 114-116 98OCH2CH3 OCH3 HCH2O 1~4'-CI-C6H4)-pyrazol-3-yl 1751, 1546, 1503, 1481, 1358, 1113, 1094, 936, 828 99OCH2CH3 OCH3 HCH2O (4-cl-C6H4)-C(CH3)=N(E) 1752, 1491, 1368, 1206, 1171, 1112, 1096, 1012, 928, 830 100OCH2CH3 OCH3 HCH2O (3,5-C12-C6H3)-C(CH3)=N(E) 1753, 1558, 1305, 1204, 1170, 1114, 1098, 1018, 994, 801 101OCH2CH3 OCH3 HCH2O H3CON=C(C6H5)C(CH3)=N (E) 1752, 1445, 1209, 1172, 1114, 1056, 1035, 1005, 994 102OCH2CH3 OCH3 HCH20 H3CON=C(CH3)C(CH3)=N (E) 50 C~
No. UR' VR" XnY' A' Physical data ~
103OCH3 NHCH3 H ~ C6Hs 1669, 1583, 1532, 1486, 1453, 1234, 1204, ~
1191, 1093 104OCH2CH3 NHCH3 H ~ C6Hs 1669, 1583, 1531, 1486, 1453, 1234, 1104, ~
1088, 753 105OCH3 OCH3 H ~ C6H5 1751, 1583, 1486, 1453, 1236, 1196, 1165, 1111, 1092, 753 106OCH2CH3 OCH3 H O C6Hs 1752, tS84, 1487, 1454, 1237, 1205, 1166, 1112, 1091, 753 109OCH3 OCH3 HCH2O 1~4-F-C6H4)-pyrazol-3-yl 1751, 1545, 1516, 1484, 1359, 1221, 1195, w 1115, 834, 746 110OCH3 NHCH3 HCH2O 1~4-F-C6H4)-pyrazol-3-yl 1669, 1545, 1516, 1483, 1462, 1436, 1290, 1271, 1230, 747 111OCH2CH3 NHCH3 HCH2O 1~4-CI-C6H4)-pyrazol-3-yl 97- 98 i 112OCH2CH3 NHCH3 HCH20 (4-CI-C6H4)-C(CH3)=N (E) 82- 83 113OCH2CH3 NHCH3 HCH2O (3,5-CI2-C6H3)-C(CH3)=N (E) 96- 97 114OCH2CH3 NHCH3 HCH20 H3CON=C(C6Hs)C(CH3)=N (E);(E) 90- 91 115OCH2CH3 NHCH3 HCH20 H3CON=(~(CH3)C(cH3)=N (E);(E) 59- 64 No. UR' VR" XnY' A' Physical data o 116 OCH3 OCH3 H O H 81-83 ~
117 OCH3 OCH3 H _ CHO 1749, 1697, 1598, 1436, 1200, 1113, 1011, N
758 o 118 OCH3 OCH3 H CH2 P(=O)~OCH3)2 1752, 1253, 1195, 1110, 1055, 1030, 855, 835, 795 119 OCH3 OCH3 H CH2 P~C6Hs)3 B~ 217-219 120 OCH3 OCH3 HCH20 5,7~CH3)2-pyrazolo[1,5a3-pyrimidin-2-yl 84- 86 121 OCH3 OCH3 HCH2O 5,7-(CH3)2-3-C2Hs-pyla- 1753, 1630, 1585, 1535, 1507, 1451, 1370, zolol1,5al-pyrimidin-2-yl 1196, 1166, 1116 122 OCH3 NHCH3 HCH20 5,7~CH3)2-~ la,1,5a]-1",i,.. iJi-l-2-yl 89- 93 w 123 OCH3 NHCH3 HCHzO 5,7~CH3)2-3-C2Hs-pyra- 134-136 zolo~l,Sal-~ - 2-yl 124 OCH3 OCH3 HCH2O 2-CH3-5-CH=NOCH3-C6H3 (E) 80- 81 125 OCH3 NHCH3 HCH20 2-CH3-5-CH=NOCH3-C6H3 (E) 89- 91 126 OCH3 OCH3 HCH2O 2-CH3-S-CH=NOC2Hs-C6H3 O 65- 67 127 OCH3 NHCH3 HCH2O 2-CH3-5-CH=NOC2H5-C6H3(E) 86-88 128 OCH3 OCH3 HCH2O 2-CH3-5-CHO-C6H3 1752, 1693, 1422, 1254, 1197, 1118, 1015, C~
No. UR' VR" XnY' A' Physical data o 130 OCH3 OCH3 H O 6-1(2-CN C6H4)-O]-p~iulidi-~-4-yl 95-97 131 OCH3 OCH3 H O 6-l(2-CI-C6H4)-Ol-pyrimidin-4-yl 74- 76 o 132 OCH3 OCH3 H O 6-l(2-F-C6H4)-O~ ;Ji-1-4-yl 1753, 1604, 1592, 1576, 1499, 1451, 1261, 1217, 1189, 1143 133 OCH3 OCH3 H O 6-l(2-Br-C6H4)-O]-~J~ ;Jill-4-yl 71- 73 134 OCH3 OCH3 H O 6-l(2,6-F2-C6H3)-O]-pyrimidin 4-yl 1753, 1596, 1573, 1500, 1451, 1260, 1217, 1200, 1176, 1146 135 OCH3 OCH3 H O 6-l(2-NO2-C6H4)-O]-pyrimidin~l yl 103-105 136 OCH3 OCH3 H O 6-[(2-CH3-C6H4)-O]_p~ilniJill_4_yl 1754, 1596, 1573, 1488, 1450, 1248, 1219, 1179, 1148, 1111 137 OCH3 OCH3 H O ~l(2-CH3O-C6H4)-Ol-pyrimidin-4-yl 1754, 1595, 1573, 1501, 1480, 1451, 1246, 1212, 1142, 1013 13P,OCH3 OCH3 H O 6-CI-~,illlill;l~ 4 yl 1754, 1559, 1444, 1351, 1258, 1213, 1088, 139 OCH3 OCH3 HCH20 2-CH3-5-lC(CH3)=NOCH3]-C6H3 (E) 1753, 1412, 1319, 1235, 1196, 1116, 1098, 1051, 1015, 874 140 OCH3 NHCH3 HCHzO 2-CH3-5-lC(CH3)=NOCH31-C6H3 (E) 96- 98 141 OCH3 OCH3 HCH2O 2-CH3-S-lC(CH3)=NOC2H5l-C6H3(E) 1754, 1413, 1318, 123S, 1195, 1170, 1116, 1093, 1050, 1014 142 OCH3 NHCH3 HCH20 2-CH3-S-[C(CH3)=NOC2Hs]-C6H3(E) 74- 76 c~
NO. UR' VR" XD Y- A' Physicaldata o 143 OCH3 OCH3 HCHzO 2-CH3-S-C(=O)CH3-C6H3 1752,1680,1414,1268,1193,1115,1013 ~
144 OCH3 NHCH3 HCH20 2-CH3-S-C(=O)CH3-C6H3 97- 99 ~n 145 OCH3 NHCH3 H O 6-[(2-CN-C6H4)-Ol-p,~ yl 1677,159S, 1581,1568,1487,1445,1248, 1~8, 1144 146 OCH3 NHCH3 H O 6-[(2-F-C6H4)-OI-pyrimidin-4-yl 1675,1606,1592,1576,1499,1450,1261, 1216, 1189, 1143 147 OCH3 NHCH3 H O 6-[(2-CI-C6H4)-O]-~ id;.~ 4 yl 1675,1599,1573,1477,1447,1383,1262, 1248, 1217, 1145 148 OCH3 NHCH3 H O 6-~(2-Br-C6H4)-O]-~ lill-4-yl 1676,1599, 1571,1451,1442,1381,1261, 1247, 1217, 1146 149 OCH3 NHCH3 H O 6-~(2,6-F2-C6H3)-O~ ll-4-yl 1675,1595,1574,1501,1479,1452,1246, ~O
1211, 1141, 1012 150 OCH3 NHCH3 H O 6-~(2-NO2-C6H4)-O]-p~.illlidin-4-yl 1675,1593,1576,1529,1450,1384,1349, 1248, 1215, 1146 151 OCH3 NHCH3 H O 6-l(2-CH3O-C6H4)-Ol 1,~.inlidin-4-yl 1676,1608,1596,1572,1500,1450, lZ60, 1199, 1175, 1147 152 OCH3 OCH3 H O 6-CI-pyrimidin-4-yl 137-139 153 OCH3 OCH3 HCH2O 2-CH3, 4-l-C6H3 86- 88 154 OCH3 NHCH3 HCHzO 2-CH3, 4-l-C6H3 1671,1531,1488,1453,1242,1188,1134, 1112, 1094, 751 c~
~' No. UR' VR~ X~ Y' A' Physi~lda~ o 155 OCH3 OCH3 H CH2O 2-CH3,5-l-C6H3 56-58 ~
156 OCH3 NHCH3 H CH2O 2-CH3,5-I-C6H3 105-106 157 OCH3 NHCH3 H CH2O 2-CH3,4~4-CH3-C6H4)-C6H3 64-67 158 OCH3 NHCH3 H CH2O 2-CH3,5~4-CH3-C6H4)-C6H3 93-94 159 OCH3 OCH3 H CH2O 3-(3-CH3-C6H4)-C6H4 1752,1602,1576,1215,1194,1181,1167, 1115,1015, m 160 OCH3 NHCH3 H CH2O 3~3-CH3-C6H4)-C6H4 1673,1603,1576,1531,1474,1215,1181, 1111,1095,777 161 OCH3 OCH3 H CH2O 2~4-CI-C6H4)-pyrimid~-4-yl 95-97 162 OCH3 NHCH3 H - CH2O 2~4-CI-C6H4)-p~lilli.li.l~ yl 97-103 O
163 oCH3 OCH3 2,3-lCH=C(C6H5)-CH=CH*] 72-74 164 OCH3 NHCH3 2,3-lCH=C(C6H5)-CH=CH*] 94-97 165 OCH3 OCH3 2,3-[CH=C(4-CI-C6H4)-CH=CH*l 63-66 166 OCH3 NHCH3 2,3-lCH=C(4-CI-C6H4)-CH=CH*] 59-64 167 OCH3 OCH3 2,3-[CH=CBr-CH=CH*] 63-66 168 OCH3 NHCH3 2,3-~CH=CBr-CH=CH*] 63-66 169 OCH3 OCH3 H CH2ON=C(CH3)-C~4-~-C6H4]=NOCH3(E;E) 1753,1508,1221,1197,1160,1116,1098, 1067,1008,841 ~
,4' ~3 i~
No. UR' vRn XnY' A' Physicaldata o 170 OCH3 NHCH3 HCH2O N=C(CH3)-CI4-F-C6H41=NOCH3 (E;E) 93-94 ~
171 OCH3 OCH3 HCH2O N=C(CH3)-C[4-F-C6H4l=NOCH2CH3 (EjE) 1754, 1508, 1221, 1196, 1116, 1096, 1036, ul 1010,975,956 ~
172 OCH3 NHCH3 HCHzO N=C(CH3)-C[4-F-C6H4]=NOCHzCH3 (EjE) 86- 88 173 OCH3 OCH3 2,3-[O-C(C6Hs)=CH~] 104-105 174 OCH3 NHCH3 2,3-[O-C(C6Hs)=CH*I 130-132 175 OCH3 OCH3 HCH2=N CH2-[3-CF3-C6H4] 1752, 1330, 1200, 1167, 1123, 1100, 1074, O 1015, 759 176 OCH3 OCH3 H _ Br 1752, 1436, 1213, 1195, 1179, 1122, 1107, 1026, 1012, 754 177 OCH3 NHCH3 H - Br 3329, 1667, 1533, 1470, 1439, 1408, 1196, 1100, 1026, 753 #: Mp. (~C), lH-NMR (ppm); IR (cm-l) ~: Bond to posi~ion 3 of the phenyl radical c~
~ f~
~ ~g~2~
Examples of the action again harmful fungi The fungicidal action of the compounds of the formula I could be 5 demonstrated by the following experiments:
The active ingredients were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil~ LN (Lutensol~ AP6, wetting agent having an emulsifying 10 and dispersing action and based on ethoxylated alkylphenols) and 10~ by weight of Emulphor~ EL (Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with water to give the desired concentration.
15 Erysiphe gr~m;n~S var. tritici (wheat mildew) Leaves of wheat seedlings (FrUhgold variety) were first treated with the agueous formulation of the active ingredient. After about 24 hours, the plants were dusted with spores of wheat 20 mildew (Erysiphe graminis var. tritici). The plants thus treated were then incubated for 7 days at 20-22'C and a relative humidity of 75-80%. The extent of fungal development was then determined.
In this test, the plants treated with an active ingredient 25 formulation cont~;n~ng 63 ppm (co,.~ound~ No. 1, 2, 3, 4, 5, 6, 7, 13, 14, lS, 16, 17 and 18) exh ~ h1 ted an infestation of 5% or less, whereas the untreated plants (control experiment) exhibited 65% infe~tation.
30 In a corresponding test, the plants treated with active ingredient formulation cont~;n~ng 63 ppm (cv...pounds No. 27-31, 38, 43, 47, 48, 55, 56, 60, 61, 63, 70, 74, 81, 88, 93 and 102) exhibited an infestation of 5~ or less, whereas the untreated plants (control experiment) exhibited 65% infestation.
Pyricularia oryzae rrice blastJ
Rice seedlings (Tai Nong 67 variety) were sprayed to run-off with the active ingredient formulation. After 24 hours, the plants 40 were sprayed with an aqueou~ spore suspension of the fungu~
Pyricularia oryzae and kept for 6 days at 22-24 C and a relative humidity of 95-99%. The evaluation wa~ carried out visually.
In this test, the plants treated with active ingredient 45 formulation cont~;n;ng 250 ppm (cv.~ unds No. 2, 3, 4, 5, 6, 7, 13, 14, 15, 16, 17, 18 and 21) exhibited an infestation of 15~ or 543 2~4~
less, whereas the untreated plants (control experiment) exhibited 70% infestation.
In a corresponding test, the plants treated with active 5 ingredient formulation containing 250 ppm (c~l..~ounds No. 27, 28, 30-32, 35, 38, 40, 41, 43-45, 48, 50, 53-56, 61, 63, 65, 67-69, 72, 74, 76-85, 87-91, 93, 94, g7, 100, 102, 110 and 112) exhibited an infestation of 15% or less, whereas the untreated plants (control experiment) exhibited 70% infestation.
Examples of action against ~ni~l pests The action of the co.~pounds of the general formula I against An; ~l pests could be demonstrated by the following experiments:
The active ingredients were prepared a) as a 0.1% strength solution in acetone or b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil~ LN ~Lutensol~ AP6, wetting agent having an emulsifying and dispersing action and based on ethoxylated alkylphenols) and 10~ by weight of Emulphor~ EL (Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with acetone in the case of a) and with water in the case of b) to give the desired concentration.
After the end of the experiments, the lowest concentration in 30 each case at which the ~o..~ounds still caused 80-100% inhibition or mortality in compArison to untreated control experiments (action threshold or m; n; m~l~ concentration) was determined.
Claims (16)
1. An alkyl phenylacetate of the formula I
(I) where R' is formyl, C1-C4-alkylcarbonyl or C1-C4-alkyl;
R" is C1-C4 - alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
V is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C2-C4-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > 1;
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl, where these groups are bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group or, together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, with the exception of compounds, I where n is 0 and R
is hydroxyl when UR' and VR" are both methoxy or ethoxy, and with the exception of compounds I where UR' and VR"
are methoxy when ~ R is methyl and Xn is 4,6-dimethyl, ~ R is methoxy and Xn is 5-nitro, and ~ R and Xn, together with the phenyl ring to which they are bonded, form a naphthyl ring.
(I) where R' is formyl, C1-C4-alkylcarbonyl or C1-C4-alkyl;
R" is C1-C4 - alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
V is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or where n is > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C2-C4-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > 1;
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl, where these groups are bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group or, together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, with the exception of compounds, I where n is 0 and R
is hydroxyl when UR' and VR" are both methoxy or ethoxy, and with the exception of compounds I where UR' and VR"
are methoxy when ~ R is methyl and Xn is 4,6-dimethyl, ~ R is methoxy and Xn is 5-nitro, and ~ R and Xn, together with the phenyl ring to which they are bonded, form a naphthyl ring.
2. An alkyl phenylacetate of the formula I as claimed in claim 1, where R is a group A1-Y1 in which Y1 is a direct bond, oxygen, sulfur, amino or alkylamino and A1 is unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, with the exception of compounds I where UR' and VR" are methoxy when ~ R is methyl and Xn is 4,6-dimethyl, and ~ R is methoxy and Xn is 5-nitro.
3. An alkyl phenylacetate of the formula I as claimed in claim 1, where R is a group CH2O-A1 in which A1 is an unsubstiutted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or an unsubstiuted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
4. An alkyl phenylacetate of the formula I as claimed in claim 1, where R is a group A2-ZaN=CRa- in which Ra is hydrogen, alkyl or haloalkyl, Za is oxygen, amino or alkylamino and A2 is hydrogen, unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
5. An alkyl phenylacetate of the formula I as claimed in claim 1, where R is a group A3-CRb=NOCHRc- in which Rb is hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted aryl, Rc is hydrogen, alkyl or cycloalkyl and A3 is unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
6. An alkyl phenylacetate of the formula I as claimed in claim 1, where R is a group A4-ON=CRd-CRe=NO-CHRf- in which Rd and Re are each hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted aryl, Rf is hydrogen, alkyl or cycloalkyl and A4 is unsubstituted or substituted alkyl, alkenyl or alkynyl or an unsubstituted or substituted saturated or partially unsaturated cyclic radical which, in addition to carbon atoms as ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen or an unsubstituted or substituted aromatic ring system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
7. An alkyl phenylacetate of the formula I as claimed in claim 1, where R and one of the radicals X, together with the phenyl ring to which they are bonded, form an unsubstituted or substituted bicyclic structure selected from the group consisting of benzofuran, benzothiophene, benzothiazole, benzoxazole, indole, isoindole and naphthalene, with the exception of compounds I where UR' and VRn are methoxy when R
and Xn, together with the phenyl ring to which they are bonded, form a naphthyl ring.
and Xn, together with the phenyl ring to which they are bonded, form a naphthyl ring.
8. A process for the preparation of the compound I as claimed in claim 1 in which U and V are each oxygen, wherein a benzaldehyde of the formula II
(II) is converted with a cyanide in a manner known per se into the corresponding cyanohydrin of the formula III
(III) III is hydrolyzed in the presence of an acid with an alcohol of the formula IV
R"OH (IV) to give a corresponding alkyl .alpha.-hydroxyphénylacetate of the formula V
(V) and V is etherified with a derivative of the formula VIa R'-L1 (VIa) where L1 is a nucleophilically substitutable leaving group to give I.
(II) is converted with a cyanide in a manner known per se into the corresponding cyanohydrin of the formula III
(III) III is hydrolyzed in the presence of an acid with an alcohol of the formula IV
R"OH (IV) to give a corresponding alkyl .alpha.-hydroxyphénylacetate of the formula V
(V) and V is etherified with a derivative of the formula VIa R'-L1 (VIa) where L1 is a nucleophilically substitutable leaving group to give I.
9. A process for the preparation of a compound I as claimed in claim 1 in which U and V are each oxygen, wherein an alkyl .alpha.-hydroxyphenylacetate of the formula V as claimed in claim 8 is first converted with a halogenating agent in a manner known per se into the corresponding alkyl .alpha.-halophenylacetate of the formula VII
(VII) where Hal is halogen, and VII is then etherified in the presence of a base with an alcohol of the formula VIb R'-OH (VIb) to give I.
(VII) where Hal is halogen, and VII is then etherified in the presence of a base with an alcohol of the formula VIb R'-OH (VIb) to give I.
10. A process for the preparation of a compound I as claimed in claim 1 in which U and V are each oxygen, wherein an alkyl .alpha.-ketophenylacetate of the formula VIII
(VIII) is reduced in a manner known per se to the corresponding alkyl .alpha.-hydroxyphenylacetate of the formula V as claimed in claim 8, and V is then a) etherified with a derivative of the formula VIa as claimed in claim 8 or b) first converted with a halogenating agent in a manner known per se into the corresponding alkyl .alpha.-halophenylacetate of the formula VII as claimed in claim 9, and VII is then etherified in the presence of a base with an alcohol of the formula VIb as claimed in claim 9 to give I.
(VIII) is reduced in a manner known per se to the corresponding alkyl .alpha.-hydroxyphenylacetate of the formula V as claimed in claim 8, and V is then a) etherified with a derivative of the formula VIa as claimed in claim 8 or b) first converted with a halogenating agent in a manner known per se into the corresponding alkyl .alpha.-halophenylacetate of the formula VII as claimed in claim 9, and VII is then etherified in the presence of a base with an alcohol of the formula VIb as claimed in claim 9 to give I.
11. A process for the preparation of a compound I in which V is amino, wherein an ester or a corresponding carboxylic acid or activated carboxylic acid of the formula VIIa (VIIa).
where L is halogen, hydroxyl, 1-imidazolyl or C1-C4-alkoxy, is reacted with an amine of the formula VIa H2N R'' VIa
where L is halogen, hydroxyl, 1-imidazolyl or C1-C4-alkoxy, is reacted with an amine of the formula VIa H2N R'' VIa
12. A composition suitable for controlling animal pests or harmful fungi and containing a solid or liquid carrier and a compound of the general formula I as claimed in claim 1.
13. Use of a compound I of the formula I*
where R' is formyl, C1-C4-alkylcarbonyl or C1-C4-alkyl;
RU is C1-C4 - alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
V is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or where n is > 1, a C3-C5 - alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C2-C4-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > 1;
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl, where these groups are bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group or, together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
for the preparation of a composition suitable for controlling animal pest or harmful fungi.
where R' is formyl, C1-C4-alkylcarbonyl or C1-C4-alkyl;
RU is C1-C4 - alkyl;
U is oxygen (-O-), sulfur (-S-), amino (-NH-) or aminooxy (-NHO-);
V is oxygen (-O-), sulfur (-S-) or amino (-NH-);
X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or where n is > 1, a C3-C5 - alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C2-C4-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group bonded to two neighboring carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
n is 0, 1, 2 or 3, and the radicals X may be different if n is > 1;
R is halogen, hydroxyl, mercapto, amino, carboxyl, carbonylamino or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl, where these groups are bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group or, together with a group X and the phenyl ring to which they are bonded, is an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
for the preparation of a composition suitable for controlling animal pest or harmful fungi.
14. A method for controlling harmful fungi, wherein the fungi or the materials, plants, soil or seeds to be protected from fungal attack are treated with an effective amount of a compound of the formula I* as claimed in claim 13.
15. A method for controlling animal pests, wherein the pests or the materials, plants, soil or seeds to be protected from them are treated with an effective amount of a compound of the formula I* as claimed in claim 13.
16. Use of a compound I* as claimed in claim 13 for controlling animal pests or harmful fungi.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4432336.0 | 1994-09-10 | ||
DE4432336 | 1994-09-10 |
Publications (1)
Publication Number | Publication Date |
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CA2199422A1 true CA2199422A1 (en) | 1996-03-14 |
Family
ID=6527949
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002199422A Abandoned CA2199422A1 (en) | 1994-09-10 | 1995-08-30 | Alkyl phenylacetates |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0781266A1 (en) |
JP (1) | JPH10505596A (en) |
AU (1) | AU3387895A (en) |
BR (1) | BR9509004A (en) |
CA (1) | CA2199422A1 (en) |
IL (1) | IL115158A0 (en) |
WO (1) | WO1996007633A1 (en) |
ZA (1) | ZA957545B (en) |
Cited By (9)
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US6255352B1 (en) * | 1997-05-28 | 2001-07-03 | Basf Aktiengesellschaft | Method for combating harmful fungi |
US8293681B2 (en) | 2008-09-19 | 2012-10-23 | Sumitomo Chemical Company, Ltd. | Seed treatment agent and method for protecting plant |
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CN1105703C (en) * | 1994-04-06 | 2003-04-16 | 盐野义制药株式会社 | 'alpha'-substituted phenylacetic acid derivative, process for producing the same, and agricultural bactericide containing the same |
US5849758A (en) * | 1995-05-30 | 1998-12-15 | American Cyanamid Company | Herbicidal 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines |
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Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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DE1274127B (en) * | 1965-10-26 | 1968-08-01 | Akad Wissenschaften Ddr | Process for the preparation of ª ‡ -Alkoxyarylessigsaeurealkylestern |
-
1995
- 1995-08-30 EP EP95930531A patent/EP0781266A1/en not_active Withdrawn
- 1995-08-30 AU AU33878/95A patent/AU3387895A/en not_active Abandoned
- 1995-08-30 WO PCT/EP1995/003405 patent/WO1996007633A1/en not_active Application Discontinuation
- 1995-08-30 CA CA002199422A patent/CA2199422A1/en not_active Abandoned
- 1995-08-30 BR BR9509004A patent/BR9509004A/en not_active Application Discontinuation
- 1995-08-30 JP JP8509172A patent/JPH10505596A/en active Pending
- 1995-09-04 IL IL11515895A patent/IL115158A0/en unknown
- 1995-09-08 ZA ZA957545A patent/ZA957545B/en unknown
Cited By (9)
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US6255352B1 (en) * | 1997-05-28 | 2001-07-03 | Basf Aktiengesellschaft | Method for combating harmful fungi |
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Also Published As
Publication number | Publication date |
---|---|
WO1996007633A1 (en) | 1996-03-14 |
AU3387895A (en) | 1996-03-27 |
EP0781266A1 (en) | 1997-07-02 |
ZA957545B (en) | 1997-03-10 |
IL115158A0 (en) | 1995-12-31 |
BR9509004A (en) | 1998-06-02 |
JPH10505596A (en) | 1998-06-02 |
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