EP0792272A1 - Substituted thiophene derivatives as pesticides and herbicides - Google Patents
Substituted thiophene derivatives as pesticides and herbicidesInfo
- Publication number
- EP0792272A1 EP0792272A1 EP95937871A EP95937871A EP0792272A1 EP 0792272 A1 EP0792272 A1 EP 0792272A1 EP 95937871 A EP95937871 A EP 95937871A EP 95937871 A EP95937871 A EP 95937871A EP 0792272 A1 EP0792272 A1 EP 0792272A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- optionally
- 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.)
- Ceased
Links
- 239000000575 pesticide Substances 0.000 title claims abstract description 7
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 150000003577 thiophenes Chemical class 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 153
- -1 alkoxy halide Chemical group 0.000 claims abstract description 134
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 103
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 101
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 40
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 32
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 150000001350 alkyl halides Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 167
- 239000000460 chlorine Chemical group 0.000 claims description 133
- 229910052801 chlorine Inorganic materials 0.000 claims description 132
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 127
- 239000011737 fluorine Substances 0.000 claims description 112
- 229910052731 fluorine Inorganic materials 0.000 claims description 112
- 150000002367 halogens Chemical class 0.000 claims description 99
- 239000002253 acid Substances 0.000 claims description 86
- 239000003085 diluting agent Substances 0.000 claims description 80
- 125000001153 fluoro group Chemical group F* 0.000 claims description 80
- 229910052760 oxygen Inorganic materials 0.000 claims description 75
- 239000001301 oxygen Substances 0.000 claims description 75
- 229910052717 sulfur Inorganic materials 0.000 claims description 75
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 74
- 229910052794 bromium Inorganic materials 0.000 claims description 74
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 67
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 67
- 239000011593 sulfur Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 62
- 150000002431 hydrogen Chemical class 0.000 claims description 50
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 239000011230 binding agent Substances 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 17
- 241000196324 Embryophyta Species 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910021645 metal ion Inorganic materials 0.000 claims description 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 150000003556 thioamides Chemical class 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- AJZYQCGTSFXNHL-UHFFFAOYSA-N 1-thiophen-3-ylpyrrolidine-2,4-dione Chemical class O=C1CC(=O)CN1C1=CSC=C1 AJZYQCGTSFXNHL-UHFFFAOYSA-N 0.000 claims description 2
- YCWFEUKOMJQTBS-UHFFFAOYSA-N 3-thiophen-3-ylpyran-2-one Chemical class O=C1OC=CC=C1C1=CSC=C1 YCWFEUKOMJQTBS-UHFFFAOYSA-N 0.000 claims description 2
- QTIVQMCGTFIROK-UHFFFAOYSA-N 5-hydroxy-4-thiophen-2-yl-1,2-dihydropyrazol-3-one Chemical class N1NC(=O)C(C=2SC=CC=2)=C1O QTIVQMCGTFIROK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 150000007578 6-membered cyclic compounds Chemical class 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- QGNMPBVBRAQJMZ-UHFFFAOYSA-N [2-butan-2-yloxy-1-butoxy-2-(ethoxy-propan-2-yloxy-propoxymethyl)sulfanyl-2-(1-methoxy-2-methylpropan-2-yl)oxy-1-(2-methylpropoxy)ethyl] thiohypofluorite Chemical compound COCC(C)(C)OC(C(SF)(OCC(C)C)OCCCC)(SC(OC(C)C)(OCCC)OCC)OC(C)CC QGNMPBVBRAQJMZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical class SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000002085 enols Chemical class 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000004999 nitroaryl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- JLPJFSCQKHRSQR-UHFFFAOYSA-N oxolan-3-one Chemical class O=C1CCOC1 JLPJFSCQKHRSQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical class O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 claims description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 15
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- 239000002585 base Substances 0.000 description 30
- 239000007858 starting material Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 150000001340 alkali metals Chemical class 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000370 acceptor Substances 0.000 description 18
- 229910052783 alkali metal Inorganic materials 0.000 description 18
- 150000002170 ethers Chemical class 0.000 description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 16
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 15
- 239000012973 diazabicyclooctane Substances 0.000 description 15
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000002798 polar solvent Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 7
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
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- 150000003918 triazines Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
Definitions
- the invention relates to new thiophene derivatives, several processes for their preparation and their use as pesticides and herbicides.
- X represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, nitro or cyano or two substituents X together with the carbon atoms to which they are attached form a saturated or unsaturated, optionally substituted ring, n for 1 , 2 or 3 and Z stands for one of the groups
- B represents hydrogen, alkyl or alkoxyalkyl, or
- a and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle, optionally interrupted by at least one heteroatom, D represents hydrogen or optionally substituted radicals from the
- a and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally unsubstituted or substituted cycle interrupted by at least one heteroatom,
- Q 1 , Q 2 , Q 3 independently of one another represent hydrogen or optionally substituted alkyl or
- E represents a metal ion equivalent or an ammonium ion
- L stands for oxygen or sulfur
- M stands for oxygen or sulfur
- R 1 for each optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or given if cycloalkyl substituted by halogen, alkyl or alkoxy, which can be interrupted by at least one heteroatom, each optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R 2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or optionally substituted by halogen optionally substituted cycloalkyl, phenyl or benzyl,
- R 3 , R 4 and R 5 independently of one another each represent optionally substituted by halogen substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent optionally substituted phenyl, phenylalkyl, phenoxy or phenylthio,
- R 6 and R 7 independently of one another represent hydrogen, in each case optionally substituted by halogen substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, represent a cycle which may be interrupted by oxygen or sulfur.
- the compounds of the formula (I) can, depending on the nature of the substituents, be present as geometric and / or optical isomers or isomer mixtures in different compositions, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them form part of the claimed invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
- A, B, D, G, Q 1 , Q 2 , Q 3 , X and n have the meaning given above Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-1 Aa) to (I- 1 Ag) and (I-1 Ba) to (I-1 Bg), if Z represents group (1),
- A, B, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
- A, B, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
- A, D, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
- the compounds of the formula (I-5) can be present in the two isomeric forms of the formulas (I-5) a and (I-5) b ,
- the compounds of the formulas (I-5) a and (I-5) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-5) a and (I-5) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- the compounds of the formulas (I-7) a and (I-7) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-7) a and (I-7) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods. For reasons of better clarity, only one of the possible isomers is listed below. This does not exclude that the compounds may optionally be in the form of the isomer mixtures or in the other isomeric form.
- A, B, D, E, L, M, Q 1 , X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above
- the compounds of the formula (I-8) can exist in the two isomeric forms of the formulas (I-8) a and (I-8) b ,
- the compounds of the formulas (I-8) a and (I-8) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-8) a and (I-8) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- A, B, D, E, L, M, Q 1 , Q 2 , Q 3 , X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above .
- A, B, D, X and n have the meanings given above if one
- A, B, D, X and n have the meanings given above, and
- R 8 represents alkyl, preferably C 1 -C 6 alkyl, intramolecularly condensed in the presence of a diluent and in the presence of a base.
- A, B, X and n have the meanings given above, if one
- A, B, X, R 8 and n have the meanings given above, condensed intramolecularly in the presence of a diluent and in the presence of a base.
- W represents hydrogen, halogen, alkyl, preferably C 1 -C 6 -alkyl, or alkoxy, preferably C 1 -C 8 -alkoxy, optionally cyclized intramolecularly in the presence of a diluent and in the presence of an acid.
- A, D, X and n have the meanings given above, if one
- Hal represents halogen, in particular chlorine or bromine, or ( ⁇ ) malonic acid derivatives of the formula (VI)
- Hal represents halogen, preferably chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
- A, B, D, R, Q 1 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base.
- A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, if
- A, B, D, Q 1 , Q 2 , Q 3 , R 8 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base.
- R 1 has the meaning given above and
- Hal represents halogen, in particular chlorine or bromine, or ⁇ ) with carboxylic anhydrides of the formula (XIII) R 1 -CO-O-CO-R 1 (XIII) in which
- R 1 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; (J) that the compounds of the formulas (I-1-c) to (I-8-c) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , R 2 , M, X and n has the meanings given above and L represents oxygen, is obtained if compounds of the formulas (I-1-a) to (I-8-a) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each with chloroformate or chloroformate thioester of the formula
- M and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder or ß) with carbon disulfide and then with alkyl halides of the formula (XVI)
- R 2 has the meaning given above and
- Hal represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a base
- R 4 and R 5 have the meanings given above and
- Hal represents halogen, in particular chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
- Me for a mono- or divalent metal, preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium, t for the number 1 or 2 and
- R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl, preferably C 1 -C 8 alkyl, optionally reacted in the presence of a diluent, O) that compounds of the formulas (I-1-g) shown above to (I-8-g) in which A, B, D, Q 1 , Q 2 , Q 3 , L, R 6 , R 7 , X and n have the meanings given above, if compounds of the ones shown above are obtained Formulas (I-1-a) to (I-8-a), in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each ⁇ ) with isocyanates or isothiocyanates of the formula (XXI)
- R 6 and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or ß) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XXII)
- L, R 6 and R 7 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
- the new substituted thiophene derivatives of the formula (I) have very good activity as pesticides, preferably as insecticides, acaricides, nematicides and herbicides and as ectoparasiticides.
- the substituted thiophene derivatives according to the invention are generally defined by the formula (I). Preferred substituents or Ranges of the radicals listed in the formulas mentioned above and below are explained below
- X preferably represents halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 -HalogenalkyI, C 1 -C 6 haloalkoxy, nitro or cyano
- n preferably represents 1, 2 or 3 Z preferably represents one of the groups
- B preferably represents hydrogen, C 1 -C 12 alkyl or C 1 -C 8 -alkoxy-C 1 -C 8 - alkyl, or A, B and the carbon atom to which they are attached preferably represent a saturated or unsaturated C 3 -C 10 spirocycle, in which one or two methylene groups which are not directly adjacent are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C 1 - C 8 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, halogen or phenyl or is substituted
- A, B and the carbon atom to which they are attached preferably represent a C 3 -C 6 spirocycle, which is interrupted by an alkylenediyl, or by an alkylenedioxyl or optionally interrupted by one or two oxygen and / or sulfur atoms an alkylenedithioyl group is substituted which forms a further five- to eight-membered spirocycle with the carbon atom to which it is attached, or
- A, B and the carbon atom to which they are attached are preferably a C 3 -C 8 -spirocycle, in which two substituents together for one optionally by C 1 -C 6 alkyl, C 1 -C 6 alkoxy or Halogen substituted saturated or mono- or polyunsaturated 5- to 8-membered cycle, which optionally contains an oxygen or sulfur atom.
- D preferably represents hydrogen, in each case optionally substituted by halogen C 1 -C 12 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 10 alkoxy-C 2 -C 8 alkyl , Poly-C 1 -C 8 alkoxy-C 2 -C 8 alkyl, C 1 -C 10 alkylthio-C 2 -C 8 alkyl, optionally by halogen, C 1 -C 4 alkyl, C 1 - C 4 alkoxy or C 1 -C 4 haloalkyl-substituted cycloalkyl having 3 to 8 ring atoms, in which one or two non-directly adjacent methyl groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or nitro substituted phenyl,
- a and D together with the atoms to which they are attached, preferably represent an alkanediyl or alkenediyl group having 3 to 6 carbon atoms which may be monosubstituted to tetrasubstituted in the same way or differently,
- a) optionally one or two non-directly adjacent methylene groups are replaced by oxygen and / or sulfur and are suitable as substituents.
- Q 1 , Q 2 , Q 3 independently of one another, preferably represent hydrogen or C 1 -C 6 alkyl or optionally substituted by halogen
- B and Q 1 together preferably represent a C 1 -C 6 -alkanediyl group which is optionally substituted by halogen or C 1 -C 6 -alkyl
- G preferably represents hydrogen (a) or one of the groups in which
- E represents a metal ion equivalent or an ammonium ion
- L stands for oxygen or sulfur and M stands for oxygen or sulfur. preferably represents in each case optionally substituted by halogen C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio-C 1 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 1 -C 8 alkyl or optionally substituted by halogen or C 1 -C 6 alkyl cycloalkyl having 3 to 8 ring atoms, in which one or two may not directly neighboring
- Methyl groups are replaced by oxygen and / or sulfur, optionally substituted by halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 - C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl substituted phenyl, optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkyl or C 1 -C 6 -Halogenalkoxy substituted phenyl-C 1 -C 6 -alkyl, for 5- or 6-membered hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl with one to three heteroatoms from the series nitrogen, oxygen and sulfur, for optionally by halogen or C 1 -C 6 -alkyl-substitute
- R 2 preferably represents in each case optionally substituted by halogen C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or poly-C 1 -C 8 - alkoxy-C 1 -C 8 alkyl, for C 3 -C 8 cycloalkyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, or for each optionally substituted by halogen, nitro, C 1 -C 6 alkyl, C 1 -C 8 alkoxy or C 1 -C 6 haloalkyl substituted phenyl or benzyl
- R J ' preferably represents C 1 -C 8 alkyl optionally substituted by halogen or in each case optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro or cyano substituted benzyl or phenyl.
- R 4 and R 3 are preferably, independently of one another, optionally
- R 6 and R 7 independently of one another preferably represent hydrogen, in each case optionally substituted by halogen C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, for phenyl optionally substituted by halogen, C 1 -C 8 haloalkyl, C 1 -C 8 alkyl or C 1 -C 8 alkoxy, optionally substituted by halogen , C 1 -C 8 alkyl, C 1 - C 8 haloalkyl or C 1 -C 8 -alkoxy-substituted benzyl or together represent C 3 -C 6 -alkanediyl in which optionally one methylene group is replaced by oxygen or sulfur.
- R 13 preferably represents hydrogen, in each case optionally substituted by halogen C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy or C 3 -C 8 -cycloalkyl or for in each case optionally by halogen, C 1 -C 6 -alkyl , C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro or cyano substituted phenyl or benzyl.
- R 14 and R 15 are preferably independently of one another hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 6 cycloalkyl, each in each case optionally by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 -HalogenaIkyl, C 1 -C 3 - halogenoalkoxy, cyano or nitro-substituted phenyl or benzyl or together represent an optionally C 1 -C 4 alkyl substituted C 4 -C 6 - alkanediyl group.
- R 16 and R 17 are the same or different and are preferably C 1 -C 6 alkyl or
- R 16 and R 17 together preferably represent a C 2 -C 4 -alkanediyl radical which may be substituted by C 1 -C 8 -alkyl or by optionally halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl.
- R 18 and R 19 independently of one another preferably represent hydrogen, optionally substituted by halogen C 1 -C 8 -alkyl or optionally by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 - Haloalkyl, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl.
- R 20 and R 21 independently of one another preferably represent C 1 -C 10 alkyl, C 3 -C 10 alkenyl, C 1 -C 10 alkoxy, C 1 -C 10 alkylamino, C 3 -C 10 alkenylamino, Di (C 1 -C 10 alkyl) amino or di (C 3 -C 10 alkenyl) amino.
- X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 - alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 -haloalkoxy , Nitro or cyano
- substituents X together with the carbon atoms to which they are attached form one, optionally by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, Nitro or cyano substituted unsaturated 5- to 7-membered carbocycle.
- n particularly preferably represents 1, 2 or 3.
- Z particularly preferably represents one of the groups
- B particularly preferably represents hydrogen, C 1 -C 10 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl or
- A, B and the carbon atom to which they are attached are particularly preferably a saturated or unsaturated C 3 -C 9 spirocycle, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C. 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, fluorine, chlorine or phenyl or substituted
- A, B and the carbon atom to which they are attached are particularly preferably a C 3 -C 6 spirocycle, which is interrupted by an alkylene diyl or an alkylene dioxyl or by an AI which may be interrupted by one or two oxygen or sulfur atoms kylendithiol group is substituted, which forms a further five- to seven-membered spirocycle with the carbon atom to which it is attached or
- A, B and the carbon atom to which they are attached are particularly preferably a C 3 -C 6 -spirocycle, in which two substituents together for an optionally by C 1 -C 5 alkyl, C 1 -C 5 alkoxy Fluorine
- Chlorine or bromine substituted saturated or mono- or polyunsaturated 5- or 6-membered cycle which optionally contains an oxygen or sulfur atom.
- D particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 10 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 8 -alkoxy-C 2 -C 6- alkyl, poly-C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl, C 1 -C 8 -alkylthio-C 2 -C 6 -alkyl, optionally by C 1 -C 4 -alkyl, C 1 -C 4 alkoxy or C 1 -C 2 haloalkyl-substituted cycloalkyl having 3 to 7 ring atoms, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl,
- a and D particularly preferably together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl grouping,
- a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by fluorine, chlorine, hydroxy, mercapto or by C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 in each case optionally substituted by fluorine or chlorine -C 4 alkylthio, C 3 -C 6 cycloalkyl, phenyl or benzyl;
- Q 1 , Q 2 , Q 3 independently of one another particularly preferably represent hydrogen or C 1 -C 4 -alkyl which is optionally substituted by fluorine or chlorine or B and Q 1 particularly preferably represent a C 1 -C 4 -alkanediyl group which may be substituted by Fluorine, chlorine or C 1 -C 4 alkyl is substituted.
- G particularly preferably represents hydrogen (a) or one of the groups
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M stands for oxygen or sulfur.
- R 1 particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 1 -C 6 alkoxy-C 1 -C 6 - alkyl, C 1 -C 6 Alkylthio-C 1 -C 6 -alkyl, poly-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or cycloalkyl having 3 to 7 ring atoms which is optionally substituted by fluorine, chlorine or C 1 -C 5 -alkyl, where one or two may not directly adjacent methylene groups are replaced by oxygen and / or sulfur, for optionally by fluorine, chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkyl, C 1 - C 3 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C
- R 2 particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 16 -alkyl, C 3 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or poly-C 1 - C 6 -alkoxy-C 1 -C 6 -alkyl, for C 3 -C 7 -cycloalkyl optionally substituted by fluorine, chlorine, C 1 -C 8 -alkyl or C 1 -C 3 -alkoxy or for each optionally substituted by fluorine, Chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 3 alkoxy or C 1 -C 8 haloalkyl substituted phenyl or benzyl.
- R 3 particularly preferably represents C 1 -C 6 -alkyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine,
- R 4 and R 5 are particularly preferably independently of one another each optionally substituted by halogen C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) ) -amino, C 1 -C 6 -alkylthio, C 3 -C 4 -alkenylthio, C 3 -C 6 -cycloalkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 -alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -
- R 6 and R 7 independently of one another particularly preferably represent hydrogen, represent in each case optionally substituted by fluorine, chlorine or bromine-substituted C 1 - C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 - C 6 -alkenyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, for optionally by fluorine, chlorine, bromine, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy, or together for C 3 -C 6 - Alkanediyl, wherein optionally a methylene group by oxygen or
- R 13 particularly preferably represents hydrogen, in each case optionally through
- R 14 and R 15 are particularly preferably independently of one another hydrogen, C 1 -C 6 alkyl, C 1 -C 8 haloalkyl, C 3 -C 6 cycloalkyl, each optionally by fluorine, chlorine, bromine, C 1 - C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, cyano or nitro substituted phenyl or benzyl or together for one optionally substituted by C 1 -C 3 alkyl C 4 -C 5 alkanediyl group
- R 16 and R 17 are the same or different and are particularly preferably C 1 -C 4 -alkyl or R 16 and R 17 together are particularly preferably a C 2 -C 3 -alkanedyl radical which may be substituted by C 1 -C 4 - Alkyl or by optionally by C 1 - C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, nitro or cyano substituted phenyl.
- X very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoromethoxy, nitro or cyano
- n very particularly preferably represents 1, 2 or 3.
- Z very particularly preferably represents one of the groups
- A, B and the carbon atom to which they are attached are very particularly preferably a saturated or unsaturated C 3 -C 8 spirocycle, in which a methylene group may have been replaced by oxygen or sulfur, and which may be mono- or polysubstituted by methyl, ethyl ,
- A, B and the carbon atom to which they are attached very particularly preferably represent a C 3 -C 6 -spirocycle, in which two substituents together represent a saturated or mono- to tri-unsaturated five- or six-membered cycle, which may be one Contains oxygen or sulfur atom.
- D very particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 8 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 - Alkynyl, C 1 -C 6 alkoxy-C 2 -C 4 alkyl, poly-C 1 -C 4 alkoxy-C 2 -C 4 alkyl, C 1 -C 4 - alkylthio-C 2 -C 4 - alkyl, C 3 -C 6 cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur, or in each case phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or nitro , Benzyl, pyridyl, thienyl, furanyl or thiazolyl or
- a and D very particularly preferably together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by Fluorine, chlorine, hydroxy, mercapto or by C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 3 -C 6 cycloalkyl, phenyl or each optionally substituted by fluorine or chlorine Benzyloxy is substituted, or, in the case of compounds of the formula (II), for one of the following groupings
- Q 1 , Q 2 , Q 3 independently of one another very particularly preferably represent hydrogen, methyl or ethyl or
- G very particularly preferably represents hydrogen (a) or one of the groups in which
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M stands for oxygen or sulfur.
- 1 very particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 14 -alkyl, C 2 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 4 -Alkylthio-C 1 -C 6 alkyl, poly-C 1 -C 4 alkoxy-C 1 -C 4 alkyl or optionally by fluorine, chlorine, methyl, ethyl, propyl, i-propyl, butyl, i-butyl or tert-butyl substituted C 3 -C 6 cycloalkyl, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, for optionally by fluorine, chlorine, bromine, methyl,
- R 2 very particularly preferably represents C 1 -C 14 -alkyl, C 3 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl or poly-C 1, each optionally substituted by fluorine or chlorine -C 4 -alkoxy-C 1 -C 6 -alkyl, for C 3 -C 6 -cycloalkyl optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl or methoxy, or for phenyl or benzyl optionally substituted by fluorine, chlorine, nitro, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy or trifluoromethyl.
- R 3 very particularly preferably represents C 1 -C 4 -alkyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine,
- R 4 and R 5 very particularly preferably independently of one another each represent C 1 -C 4 -alkyl which is optionally substituted by fluorine or chlorine, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C 1 -C 4 ) 4- alkyl) -amino, C 1 -C 4 -alkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2 -alkoxy, C 1 -C 2 -fluoroalkoxy, C 1 -C 2 Alkylthio, C 1 -C 2 fluoroalkylthio or C 1 -C 3 alkyl substituted phenyl, phenoxy or phenylthio.
- R and R independently of one another very particularly preferably represent hydrogen, in each case optionally substituted by fluorine, chlorine or bromine, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyl, C 1 - C 4 alkoxy-C 1 -C 4 -alkyl, optionally substituted by fluorine, chlorine, bromine, C 1 - C 4 haloalkyl, C 1 -C 4 alkyl or C 1 -C 4 -Alkoxy substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy, or together for C 4 -C 6 alkane diyl , in which a methylene group is optionally replaced by oxygen or sulfur.
- radicals X can be the same or different.
- reaction process can be represented as follows:
- Hal represents chlorine or bromine, acylated (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968) or if acylamino acids of the formula (XXV)
- A, B, D, X and n have the meanings given above, esterified (Chem. Ind. (London) 1568 (1968)).
- Hal stands for chlorine or bromine, acylated according to Schotten-Baumann (Organikum, VEB German Publishing House of Sciences, Berlin 1977, p. 505)
- the substituted cyclic aminocarboxylic acids of the formula (XXVIa), in which A and B form a ring, are generally obtainable after the Bucherer-Bergs synthesis or after the Strecker synthesis and are each obtained in different isomer forms.
- ⁇ the isomers
- the radicals R and the carboxyl group are in equatorial fashion
- the isomers are equatorial
- Hal represents chlorine or bromine
- A, B, D, X and n have the meanings given above,
- A, B and R 8 have the meanings given above, with thienylacetic acid halides of the formula (XXIV) in which X and n have the meanings given above and
- Hal stands for chlorine or bromine. acylated (Chem. Reviews 52, 237-416 (1953)).
- A, B and R 8 have the meanings given above and
- Hal represents chlorine or bromine, alkylated.
- the compounds of the formulas (XXX) and (XXXI) are generally known compounds and / or can be prepared in a simple manner by known processes
- the compounds of the formula (IV) required as starting materials in process (C) above are generally known compounds and / or can be prepared in a simple manner by known processes.
- the compounds of the formula (IV) required as starting materials in process (C) above are generally known compounds and / or can be prepared in a simple manner by known processes.
- A, B, W, X, n and R 8 have the meanings given above are new.
- A, B and W have the meanings given above and
- Hal stands for halogen, especially chlorine or bromine, acylated in the presence of strong bases (see e.g. M S. Chambers, E. J. Thomas, DJ. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228).
- halocarbonyl ketene of the formula (V) required as starting materials in the above process (Da) are new. They can be produced in a simple manner by methods known in principle (cf. for example Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE 1 945 703). This gives the compounds of the formula (V)
- Hal stands for chlorine or bromine if one
- X and n have the meanings given above, with acid halides, such as, for example, thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate in the presence of catalysts, such as, for example, diethylformamide, methyl sterylformamide or triphenylphosphine and if appropriate in the presence of bases such as Pyridine or triethylamine.
- acid halides such as, for example, thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide
- catalysts such as, for example, diethylformamide, methyl sterylformamide or triphenylphosphine and if appropriate in the presence of bases such as Pyridine or triethylamine.
- thienylmalonic acids of the formula (XXXIV) are known compounds of organic chemistry and can easily be prepared according to known ones
- R 8 , X and n have the meanings given above, are known in some cases and can be prepared by generally known methods of organic chemistry (cf., for example, Tetrahedron Lett. 27, 2763 (1986) and Organikum VEB German Publishing House of Sciences, Berlin 1977, P. 587 ff).
- a and D have the meanings given above, are known in some cases and / or can be prepared by methods known from the literature (cf. for example Liebigs Ann. Chem. 585.6 (1954); Reactions of Organic Synthesis, C. Ferri, pages 212, 513; Georg Thieme Verlag Stuttgart, 1978; Liebigs
- a and D have the meanings given above, are commercially available, generally known or accessible by known processes
- A, B, D, Q 1 , X, n and R 8 have the meanings given above are new. They can be produced using methods that are known in principle.
- the compounds of the formula (X) are obtained if 5-thienyl-4-ketocarboxylic acids of the formula (XXXV)
- X, A, B, D, Q 1 and n have the meanings given above, esterified (see, for example, Organikum, 15th edition, Berlin, 1977, page 499).
- A, B, D, Q 1 , X and n have the meanings given above and
- R 8 and R 8 are the same or different and represent alkyl, preferably C 1 -C 6 alkyl, optionally saponified and decarboxylated in the presence of a diluent and optionally in the presence of a base or acid (see, for example, Organikum, 15th edition, Berlin , 1977, pages 519 to 521).
- A, B, D, Q, X, R 8 , R 8 ' and n have the meanings given above are available if dicarboxylic acid half-ester chlorides of the formula (XXXIX),
- A, B, D, Q 1 and R 8 have the meanings given above and Hal represents chlorine or bromine, with thienylacetic acid ester of the formula (XXXII) in which R 8 ' , X and n have the meanings given above, acylated in the presence of a diluent and in the presence of a base (see, for example, M S. Chambers, EJ Thomas, DJ Williams, J. Chem. Soc. Chem. Commun, (1987), 1228).
- the compounds of the formulas (XXXII) and (XXXIX) are generally known
- A, B, D, Q 1 , Q 2 , Q 3 , X, n and R 8 have the meaning given above are new. They can be produced using methods that are known in principle.
- the compounds of the formula (XI) are obtained if 6-thienyl-5-ketocarboxylic acids of the formula (XL)
- X, A, B, D, Q 1 , Q 2 , Q 3 and n have the meanings given above, esterified, (see, for example, Organikum, 15th edition, Berlin, 1977, page 499).
- X and n have the meanings given above, Me for mono- or divalent metal ions, such as lithium and
- A, B, D, Q 1 , Q 2 , Q 3 , X, R 8 , R 8 ' and n have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base or acid and saponified and decarboxylated (cf. e.g. Organikum, 15th edition, Berlin, 1977, pages 519 to 521).
- A, B, D, Q 1 , Q 2 , Q 3 Z, R 8 , R 8 ' and n have the meanings given above are new and obtainable if dicarboxylic acid half-ester chlorides of the formula (XLIII),
- A, B, D, Q 1 , Q 2 , Q 3 and R 8 have the meanings given above and
- Hal represents chlorine or bromine, with thienylacetic acid esters of the formula (XXXII) in which
- X, R 8 ' and n have the meanings given above, acylated in the presence of a diluent and in the presence of a base (see, for example, MS Chambers, EJ Thomas, DJ Williams, J Chem Soc Chem Commun, (1987), 1228)
- the compounds of the formulas (XXXII) and (XLIII) are generally known compounds of organic chemistry and / or can be prepared in a simple manner by methods known in principle (cf. for example EP-A-0 307 103)
- the acid halides of the formula (XII), carboxylic anhydrides of the formula (XIII) which are also required as starting materials for carrying out the processes (I), (J), (K), (L), (M), (N) and (O) , Chloroformic acid ester or chloroformic acid thioester of the formula (XIV), chloromothio formic acid ester or chlorodithio formic acid ester of the formula (XV), alkyl halides of the formula
- XVI sulfonic acid chlorides of the formula (XVII), phosphorus compounds of the formula (XVIII) and metal hydroxides, metal alkoxides or amines of the formula (XIX) and (XX) and isocyanates of the formula (XXI) and carbamic acid chlorides of the formula (XXII) are generally known compounds organic or inorganic chemistry.
- Process (A) is characterized in that compounds of the formula (II) in which A, B, D, X, n and R 8 have the meanings given above are subjected to an intramolecular condensation in the presence of bases.
- Hydrocarbons such as toluene and xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and alcohols, such as methanol, ethanol, propanol, isopropanol , Butanol, isobutanol and tert-butanol.
- ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether
- polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone
- alcohols such as methanol, ethanol, propanol, isopropanol , Butanol
- All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (A) according to the invention.
- alkali metals such as sodium or potassium can be used.
- alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
- the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. Process (A) according to the invention is generally carried out under normal pressure.
- reaction components of the formula (II) and the deprotonating bases are generally employed in approximately double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
- Process (B) is characterized in that compounds of the formula (III) in which A, B, X, n and R 8 have the meanings given above are subjected to intramolecular condensation in the presence of a base and a diluent.
- All inert organic solvents can be used as diluents in process (B) according to the invention.
- Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- Alcohols such as methanol, ethanol, propanol,
- Iso-propanol, butanol, iso-butanol and tert-butanol can be used.
- All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (B) according to the invention.
- Alkali metals such as sodium or potassium can also be used.
- alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butoxide can be used.
- reaction temperatures can be varied within a substantial range when carrying out process (B) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between
- Process (B) according to the invention is generally carried out under normal pressure.
- reaction components of the formula (III) and the deprotonating bases are generally employed in approximately double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
- inert organic solvents can be used as diluents in process (C) according to the invention.
- Hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone are preferably used.
- Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
- the acid used can also serve as a diluent.
- Acids which can be used in process (C) according to the invention are all customary inorganic and organic acids, such as, for example, hydrohalic acids, sulfuric acid, alkyl-, aryl- and haloalkylsulfonic acids, in particular halogenated alkylcarboxylic acids such as trifluoroacetic acid.
- the reaction temperatures can be varied within a substantial range when carrying out process (C) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
- Process (C) according to the invention is generally carried out under normal pressure.
- reaction components of the formulas (IV) and the acid for example in equimolar amounts. It is optionally also possible to use the acid as a solvent or as a catalyst.
- All inert organic solvents can be used as diluents in the processes (D- ⁇ ) and (D- ⁇ ) according to the invention.
- Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (D- ⁇ ) and (D- ⁇ ).
- Alkali metal and alkaline earth metal oxides are preferably usable,
- Alkali metals such as sodium or potassium can also be used.
- alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride
- alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butoxide
- reaction temperatures can be varied within a substantial range when carrying out process (D- ⁇ ) and (D- ⁇ ) according to the invention.
- temperatures between -20 ° C and 250 ° C, preferably between 0 ° C and 150 ° C.
- Process (D- ⁇ ) and (D- ⁇ ) according to the invention are generally carried out under normal pressure.
- the reaction components of the formulas (V) and (VII) or (VI) and (VII) and the deprotonating bases which may be used are generally employed in approximately equimolar amounts on. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
- Process (E) according to the invention is characterized in that carbonyl compounds of the formula (VIII) are reacted with ketonic acid halides of the formula (II) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.
- Xylene also ethers, such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- ethers such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether
- polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- reaction temperatures can be varied within a substantial range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C. Process E) is advantageously carried out under normal pressure.
- the acid acceptors are expediently approximately equimolar Quantities.
- Process (F) according to the invention is characterized in that thioamides of the formula (IX) are reacted with ketonic acid halides of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
- All inert organic solvents can be used as diluents in process F).
- Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone are preferably usable.
- Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can preferably be used.
- the reaction temperatures can be varied within a substantial range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 20 ° C and 220 ° C.
- Process F) is advantageously carried out under normal pressure.
- the reaction components of the formulas (IX) and (V) in which A, X and n have the meanings indicated above and Hal represents halogen and, if appropriate, the acid acceptors are advantageously employed in approximately equimolar amounts.
- the process (G) is characterized in that compounds of the formula (X) in which A, B, D, Q 1 , X, n and R 8 have the meaning given above, in the presence of a base and optionally in the presence of a Diluent undergoes intramolecular condensation.
- All inert organic solvents can be used as diluents in process (G) according to the invention.
- Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
- All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (G) according to the invention.
- Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used.
- phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxy
- Alkali metals such as sodium or potassium can also be used.
- alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
- the reaction temperatures can be carried out when carrying out the process according to the invention
- Process (G) can be varied within a wide range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. Process (G) according to the invention is generally carried out under normal pressure.
- reaction components of the formula (X) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
- the process (H) is characterized in that compounds of the formula (XI) in which A, B, D, Q 1 , Q 2 , Q 3 , X, n and R 8 have the meaning given above, in the presence of a Base and optionally in the presence of a diluent, an intramolecular condensation.
- All inert organic solvents can be used as diluents in process (H) according to the invention.
- Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
- Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
- All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (H) according to the invention.
- Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used.
- phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxy
- Alkali metals such as sodium or potassium can also be used.
- alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
- reaction temperatures can be varied within a substantial range when carrying out process (H) according to the invention. In general one works at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C
- Process (H) according to the invention is generally carried out under normal pressure.
- process (H) according to the invention the process (H) according to the invention.
- reaction components of the formula (XI) and the deprotonating bases generally in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
- the process (I ⁇ ) is characterized in that compounds of
- Diluents which can be used in process (I ⁇ ) according to the invention are all solvents which are inert to the acid halides.
- Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, can preferably be used.
- ketones such as acetone and methyl isopropyl ketone
- ethers such as diethyl ether, tetrahydrofuran and dioxane
- carboxylic acid esters such as ethyl acetate
- strongly polar solvents such as dimethyl sulfoxide and sulfolane
- Suitable acid binders for the reaction according to process (I ⁇ ) according to the invention are all customary acid acceptors.
- Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, can preferably be used.
- reaction temperatures can also be varied within a substantial range in process (I ⁇ ) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
- process (I ⁇ ) the starting materials of the formulas (I-1-a) to (I-8-a) and the carboxylic acid shauride of the formula (XII) are generally used in approximately equivalent amounts.
- carboxylic acid chloride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
- Process (Iß) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted with carboxylic anhydrides of the formula (XIII), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
- Diluents which can be used in the process (Iß) according to the invention are preferably those diluents which are also suitable for
- reaction temperatures in the process (Iß) according to the invention can also be used within a relatively large range when using carboxylic anhydrides
- Range can be varied. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
- the starting materials of the formulas (I-1-a) to (I-8-a) and the carboxylic anhydride of the formula (XIII) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
- the procedure is such that diluent and excess carboxylic anhydride and the resulting carboxylic acid are obtained by distillation or by washing with an organic solvent or with
- Process (J) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, with chloroformates or chloroformates of formula (XIV) Acid binders used in the reaction according to the invention
- Process (J) all customary acid acceptors into consideration.
- Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide
- Diluents which can be used in process (J) according to the invention are all solvents which are inert to the chloroformic acid esters or chloroformic acid urethiol esters.
- Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o -Dichlorobenzene, also ketones, such as acetone and methyl isopropyl ketone, further ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane
- reaction temperatures in carrying out process (J) according to the invention can be varied within a substantial range. If one works in the presence of a diluent and an acid binder, the reaction temperatures are generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C
- Process (J) according to the invention is generally carried out under normal pressure
- the starting materials of the formulas (I-1-a) to (I-8-a) and the corresponding chloroformate or chloroformate diol ester of the formula (XIV) are generally used in approximately equivalent amounts also possible, one or the other component in a larger excess (up to 2 mol) to use.
- the working up is then carried out by customary methods.
- the general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent
- Possible diluents added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also haloalkanes
- the enolate salt of the compounds (I-1-a) to (I-8-a) can be dispensed with the further addition of acid binders
- customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
- the reaction can be carried out under atmospheric pressure or under elevated pressure, preferably under atmospheric pressure. Working up is carried out by customary methods
- the molar amount or an excess of sulfur is used per mole of starting compounds of the formulas (I-1-a) to (I-8-a) carbon too.
- the process is preferably carried out at temperatures from 0 to 50 ° C. and in particular at 20 to 30 ° C.
- All conventional proton acceptors can be used as bases in the process (Kß).
- Nitrogen bases examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
- Common solvents can be used as diluents in this process .
- Aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethyl englycol, nitriles such as acetonitrile, ethers such as tetrahydrofuran or dioxane, amides such as dimethylformamide or other polar solvents such as dimethyl sulfoxide or sulfolane can preferably be used.
- the further reaction with the alkyl halide of the formula (XVI) is preferably carried out at 0 to 70 ° C. and in particular at 20 to 50 ° C.
- at least the equimolar amount of alkyl halide is used.
- the processing is again carried out using customary methods.
- Process (L) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with sulfonic acid chlorides of the formula (XVII) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
- Possible diluents added are all inert polar organic solvents such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
- Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
- the enolate salt of the compounds (I-1-a) to (I-8-a) is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tert-butoxide)
- strong deprotonating agents such as sodium hydride or potassium tert-butoxide
- acid binders can be dispensed with.
- customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
- the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
- the processing takes place according to usual methods.
- Process (M) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted with phosphorus compounds of the formula (XVIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder Manufacturing process (M) is used to obtain compounds of
- Any inert, polar organic solvents such as ethers, amides, nitriles, carboxylic acid esters, sulfides, sulfones, sulfoxides, etc. are suitable as diluents which may be added.
- Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
- Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
- the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
- the processing takes place according to the usual methods of organic chemistry.
- the end products obtained are preferably purified by crystallization, chromatographic purification or by so-called "distillation", i.e. Removal of volatiles in vacuo.
- Process (N) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with metal hydroxides or metal alkoxides of the formula (XIX) or amines of the formula (XX), if appropriate in the presence of a diluent.
- diluents are ethers such as tetrahydrofuran, dioxane,
- Process (N) according to the invention is generally carried out under normal pressure.
- the reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.
- Process (O) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with (O ⁇ ) compounds of the formula (XXI), if appropriate in the presence of a diluent and if appropriate in the presence of a Reacting catalyst or (Oß) with compounds of formula (XXII) optionally in the presence of a diluent and optionally in the presence of an acid binder.
- Possible diluents added are all inert organic solvents, such as ethers, amides, nitriles, sulfones or sulfoxides
- catalysts can be added to accelerate the reaction.
- Organotin compounds such as dibutyltin dilaurate, can be used very advantageously as catalysts. It is preferably carried out at normal pressure.
- Oß In the preparation process (Oß), about 1 mol of carbamic acid chloride of the formula (XXII) at 0 to 150 ° C., preferably, is used per mole of starting compound of the formulas (I-1-a) to (I-8-a) at 20 to 70 ° C
- Possible diluents added are all inert polar organic solvents, such as ethers, amides, nitriles, carboxylic acid esters, sulfones, sulfoxides or halogenated hydrocarbons
- the active compounds according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector.They are resistant to normally sensitive and resistant species and to all or individual stages of development
- the pests mentioned above include
- Onychiurus armatus From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria, Supella spp .. From the order of the Dermaptera e.g. Forficula auricularia.
- Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
- Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp., Panstrongylus spp ..
- Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis, spp.
- Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis,
- Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
- Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
- Cacoecia podana Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
- Anobium punctatum Rhizopertha dominica
- Acanthoscelides obtectus Acanthoscelides obtectus
- Hylotrupes bajulus Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodalazaisyo spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,
- Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
- Oestrus spp. Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Simulium spp., Eusimulium spp., Phlebia spp.
- Siphonaptrida e.g. Xenopsylla spp., Ceratophyllus spp., Pulex spp., Ctenocephalides spp ..
- Acarina e.g. Myocoptes spp., Otodectes spp., Acarus siro, Argas spp., Ornithodoros spp., Ornithonyssus spp., Dermanyssus spp., Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommommas spp spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,
- Actinedida Prostigmata
- Acaridida Acaridida
- Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
- Tyrophagus spp. Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
- the active compounds according to the invention are notable for high insecticidal and acaricidal activity.
- the active compounds according to the invention can furthermore be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that are on
- the active compounds according to the invention can e.g. can be used for the following plants:
- the compounds are suitable for total weed control e.g. on industrial and track systems and on paths and squares with and without tree cover.
- the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control be used in annual crops.
- the active compounds according to the invention are very well suited for the selective control of monocotyledon weeds in dicotyledon crops in the pre- and post-process. You can, for example, in cotton or sugar beet with very good
- the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers
- formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
- extenders that is to say liquid solvents and / or solid carriers
- surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- aromatics such as xylene, toluene, or alkylnaphthalenes
- chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
- alcohols such as butanol or glycol and their ethers and esters
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene
- Fatty acid esters polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
- the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants,
- Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
- Particularly cheap mixing partners are e.g. the following:
- Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
- Tebuconazole Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon,
- Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
- Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fu
- Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
- Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
- Tebufenozid Tebufenpyrad
- Tebupirimphos Teflubenzuron
- Tefluthrin Temephos
- anilides e.g. Diflufenican and Propanil
- Aryl carboxylic acids e.g. Dichloropicolinic acid, dicamba and picloram
- Aryloxy alkanoic acids e.g. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr
- Aryloxy-phenoxy-alkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl,
- Carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and
- Methabenzthiazuron hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g.
- Amidosulfuron bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuronethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g.
- Atrazin cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. Hexazinone, metamitron and metribuzin; Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
- Triazinones e.g. Hexazinone, metamitron and metribuzin
- Others such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone,
- the active ingredient according to the invention can furthermore be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
- Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
- the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
- the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
- the application takes place in a customary manner adapted to the application forms.
- the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
- the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. For example, they show excellent
- the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
- arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
- the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, paste boluses, the feed-through method, suppositories, by parenteral administration, such as e.g. by
- Injection intramuscular, subcutaneous, intravenous, intraperitonal, etc.
- implants by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb straps,
- the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or as a chemical
- reaction mixture is mixed with 170 ml of water
- the combined aqueous phases are acidified at 0 to 10 ° C with about 22 ml of concentrated hydrochloric acid, the precipitate is suction filtered and dried. In this way, 14.3 g ( ⁇ 92% of theory) of the compound shown above are obtained from the melting point.
- Example (I-2 Ba-1) Analogously to Example (I-2 Ba-1), starting from the compound according to Example (III-A-2), the compound shown above is obtained as pale yellow crystals with a melting point of 239 ° C. (dec.).
- a solution of the compound according to Example (XXXII-1) in 500 ml of 10% aqueous KOH is heated to reflux for 3 hours. After cooling, it is diluted with water and acidified with concentrated hydrochloric acid while cooling with ice. The aqueous solution is extracted several times with dichloromethane; the organic phase is dried over MgSO 4 and filtered. The solvent is then removed in vacuo.
- Morpholine-CH 2 3.76 ppm (m, 2H, morpholine-CH 2 ), 4.09 ppm (s, 2H, thienyl-CH 2 -), 4.37 ppm (m, 2H, morpholine-CH 2) ), 6.60 ppm (s, 1H, 4-thiophene-H).
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
- Bean plants Phaseolus vulgaris
- which are severely affected by all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are treated by dipping into the active compound preparation of the desired concentration.
- the kill is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
- the compounds according to Preparation Examples I-2 Ba-1 and I-2 Bc-1 at an exemplary active ingredient concentration of 0.1% caused at least 98% to be killed after 7 days.
- Test animals Adult suckled females
- Dimethyl sulfoxide 20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution with the same solvent.
- the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effectiveness check is carried out after 7 days on the inhibition of egg laying. An effect of 100% means that no tick has laid eggs.
- the compounds according to the preparation examples I-2 B-a-1, I-2 B-b-1 and I-2 B-c-1 with an exemplary active ingredient concentration of 20 ⁇ g / animal have an activity of 100%.
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Abstract
The invention relates to novel thiophene derivatives of formula (I) in which X is halogen, alkyl, alkoxy, alkylthio, alkyl halide, alkoxy halide, nitro or cyano or two substituents X together with the carbon atoms to which they are bonded form a saturated or unsaturated, possibly substituted ring, n is a number from 1 to 3 and Z is one of the groups (1), (2), (3), (4), (5), (6), (7) or (8), in which A, B, D, G, Q?1, Q2 and Q3¿ have the meanings given in the description. Process for their production and their use as pesticides and herbicides.
Description
SUBSTITUIERTE THIOPHENDERIVATE ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL UND HERBIZIDE SUBSTITUTED THIOPHENE DERIVATIVES AS A PEST CONTROL AND HERBICIDE
Die Erfindung betrifft neue Thiophenderivate, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Herbizide. The invention relates to new thiophene derivatives, several processes for their preparation and their use as pesticides and herbicides.
Von 4-(Aryl- und aralkyl-thienyl)-3-hydroxy-3-pyrrolin-2,5-dion-Derivaten sind pharmazeutische Eigenschaften bekannt (ZA 8006-788) Pharmaceutical properties of 4- (aryl- and aralkyl-thienyl) -3-hydroxy-3-pyrroline-2,5-dione derivatives are known (ZA 8006-788)
Es wurden nun neue Thiophenderivate der Formel (I) New thiophene derivatives of the formula (I)
gefunden, in welcher X für Halogen, Alkyl, Alkoxy, Alkylthio, Halogenalkyl, Halogenalkoxy, Nitro oder Cyano steht oder zwei Substituenten X gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gesättigten oder ungesättigten, gegebenenfalls substituierten Ring bilden, n für 1, 2 oder 3 steht und Z für eine der Gruppen
found in which X represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, nitro or cyano or two substituents X together with the carbon atoms to which they are attached form a saturated or unsaturated, optionally substituted ring, n for 1 , 2 or 3 and Z stands for one of the groups
(8) steht,(8) stands,
worin für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Alkylthioalkyl, gegebenenfalls durch mindestens ein Heteroatom unterbrochenes gesättigtes oder ungesättigtes, gegebenenfalls substituiertes Cycloalkyl oder jeweils gegebenenfalls durch Halogen, Alkyl, Halogenalkyl, Alkoxy oder Nitro substituiertes Aryl, Arylalkyl oder Hetaryl steht, wherein represents hydrogen, in each case optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, optionally saturated or unsaturated, optionally substituted cycloalkyl interrupted by at least one heteroatom or in each case optionally substituted by halogen, alkyl, haloalkyl, alkoxy or nitro aryl, arylalkyl or hetaryl ,
B für Wasserstoff, Alkyl oder Alkoxyalkyl steht, oder B represents hydrogen, alkyl or alkoxyalkyl, or
A und B gemeinsam mit dem Kohlenstoffatom an das sie gebunden sind für einen gesattigten oder ungesättigten, gegebenenfalls durch mindestens ein Heteroatom unterbrochenen un substituierten oder substituierten Cyclus stehen,
D für Wasserstoff oder gegebenenfalls substituierte Reste aus derA and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle, optionally interrupted by at least one heteroatom, D represents hydrogen or optionally substituted radicals from the
Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkylthioalkyl, gegebenenfalls durch mindestens ein Heteroatom unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Arylalkyl, Aryl, Hetarylalkyl oder Hetaryl steht oder Row alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, optionally saturated or unsaturated cycloalkyl, arylalkyl, aryl, hetarylalkyl or hetaryl interrupted by at least one heteroatom or
A und D gemeinsam mit den Atomen an die sie gebunden sind für einen gesättigten oder ungesättigten und gegebenenfalls durch mindestens ein Heteroatom unterbrochenen unsubstituierten oder substituierten Cyclus stehen, Q1, Q2, Q3 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertes Alkyl stehen oder A and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally unsubstituted or substituted cycle interrupted by at least one heteroatom, Q 1 , Q 2 , Q 3 independently of one another represent hydrogen or optionally substituted alkyl or
B und Q1 gemeinsam für eine gegebenenfalls substituierte Alkandiylgruppe stehen, B and Q 1 together represent an optionally substituted alkanediyl group,
G für Wasserstoff (a) oder für eine der Gruppen G for hydrogen (a) or for one of the groups
steht, worin stands in what
E für ein Metallionäquivalent oder ein Ammoniumion steht, E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht, M für Sauerstoff oder Schwefel steht, L stands for oxygen or sulfur, M stands for oxygen or sulfur,
R1 für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Alkylthioalkyl, Polyalkoxyalkyl oder gegebenen
falls durch Halogen, Alkyl oder Alkoxy substituiertes Cycloalkyl, das durch mindestens ein Heteroatom unterbrochen sein kann, jeweils gegebenenfalls substituiertes Phenyl, Phenylalkyl, Hetaryl, Phenoxyalkyl oder Hetaryloxyalkyl steht, R2 für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Polyalkoxyalkyl oder für jeweils gegebenenfalls substituiertes Cycloalkyl, Phenyl oder Benzyl steht, R 1 for each optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or given if cycloalkyl substituted by halogen, alkyl or alkoxy, which can be interrupted by at least one heteroatom, each optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R 2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or optionally substituted by halogen optionally substituted cycloalkyl, phenyl or benzyl,
R3, R4 und R5 unabhängig voneinander für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkoxy, Alkylamino, Dialkylamino, Alkylthio, Alkenylthio, Cycloalkylthio und für jeweils gegebenenfalls substituiertes Phenyl, Phenylalkyl, Phenoxy oder Phenylthio stehen, R 3 , R 4 and R 5 independently of one another each represent optionally substituted by halogen substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent optionally substituted phenyl, phenylalkyl, phenoxy or phenylthio,
R6 und R7 unabhängig voneinander für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, für gegebenenfalls substituiertes Phenyl, für gegebenenfalls substituiertes Benzyl stehen, oder gemeinsam mit dem N-Atom, an das sie gebunden sind, für einen gegebenenfalls durch Sauerstoff oder Schwefel unterbrochenen Cyclus stehen. ie Verbindungen der Formel (I) können, auch in Abhängigkeit von der Art der Substituenten, als geometrische und/oder optische Isomere oder Isomerengemische, in unterschiedlicher Zusammensetzung vorliegen, die gegebenenfalls in üblicher Art und Weise getrennt werden können. Sowohl die reinen Isomeren als auch die Isomerengemische, deren Herstellung und Verwendung sowie diese enthaltende Mittel sind Bestandteile der beanspruchten Erfindung. Im folgenden wird der Einfachheit halber jedoch stets von Verbindungen der Formel (I) gesprochen, obwohl sowohl die reinen Verbindungen als gegebenenfalls auch Gemische mit unterschiedlichen Anteilen an isomeren Verbindungen gemeint sind. R 6 and R 7 independently of one another represent hydrogen, in each case optionally substituted by halogen substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, represent a cycle which may be interrupted by oxygen or sulfur. The compounds of the formula (I) can, depending on the nature of the substituents, be present as geometric and / or optical isomers or isomer mixtures in different compositions, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them form part of the claimed invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
Unter Einbeziehung der Bedeutungen (1) bis (8) der Gruppe Z ergeben sich folgende hauptsächliche Strukturen (I-1) bis (I-8):
Including the meanings (1) to (8) of group Z, the following main structures (I-1) to (I-8) result:
worin wherein
A, B, D, G, Q1 , Q2, Q3, X und n die oben angegebene Bedeutung haben, und unter Berücksichtigung der Stellung des Substituenten Z im Thiophenring die folgenden Strukturen (I-1A) bis (I-8 A) und (I-IB) bis (I-8B): A, B, D, G, Q 1 , Q 2 , Q 3 , X and n have the meaning given above, and taking into account the position of the substituent Z in the thiophene ring, the following structures (I-1A) to (I-8 A ) and (I-IB) to (I-8B):
worin wherein
A, B, D, G, Q1, Q2, Q3, X und n die oben angegebene Bedeutung haben
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-1 A-a) bis (I-1 A-g) sowie (I-1 B-a) bis (I-1 B-g), wenn Z für die Gruppe (1) steht, A, B, D, G, Q 1 , Q 2 , Q 3 , X and n have the meaning given above Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-1 Aa) to (I- 1 Ag) and (I-1 Ba) to (I-1 Bg), if Z represents group (1),
worin wherein
A, B, D, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenenA, B, D, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n the above
Bedeutungen besitzen. Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) undHave meanings. Including the different meanings (a), (b), (c), (d), (e), (f) and
(g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-2 A-a) bis (I-2 A-g) sowie (I-2 B-a) bis (I-2 B-g), wenn Z für die Gruppe (2) steht,
worin (g) of group G, the following main structures (I-2 Aa) to (I-2 Ag) and (I-2 Ba) to (I-2 Bg) result if Z stands for group (2), wherein
A, B, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebene Bedeutungen haben. A, B, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-3 A-a) bis (I-3 A-g) sowie (I-3 B-a) bis (I-3 B-g), wenn Z für die Gruppe (3) steht, Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-3 Aa) to (I- 3 Ag) and (I-3 Ba) to (I-3 Bg), if Z stands for group (3),
worin wherein
A, B, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenen Bedeutungen besitzen. A, B, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-4 A-a) bis (I-4 A-g) sowie (I-4 B-a) bis (I-4 B-g), wenn Z für die Gruppe (4) steht, Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-4 Aa) to (I- 4 Ag) and (I-4 Ba) to (I-4 Bg) if Z stands for group (4),
worin wherein
A, D, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenen Bedeutungen besitzen. A, D, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
Die Verbindungen der Formel (I-5) können in Abhängigkeit von der Stellung des Substituenten G in den zwei isomeren Formen der Formeln (I-5)a und (I-5)b vorliegen, Depending on the position of the substituent G, the compounds of the formula (I-5) can be present in the two isomeric forms of the formulas (I-5) a and (I-5) b ,
was durch die gestrichelte Linie in der Formel (I-5) zum Ausdruck gebracht werden soll. which is to be expressed by the dashed line in formula (I-5).
Die Verbindungen der Formeln (I-5)a und (I-5)b können sowohl als Gemische als auch in Form ihrer reinen Isomeren vorliegen. Gemische der Verbindungen der Formeln (I-5)a und (I-5)b lassen sich gegebenenfalls in an sich bekannter Weise durch physikalische Methoden trennen, beispielsweise durch chromatographische Methoden. The compounds of the formulas (I-5) a and (I-5) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-5) a and (I-5) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
Aus Gründen der besseren Übersichtlichkeit wird im folgenden jeweils nur eines der möglichen Isomeren aufgeführt. Das schließt nicht aus, daß die Verbindungen
gegebenenfalls in Form der Isomerengemische oder in der anderen isomeren Form vorliegen können. For reasons of better clarity, only one of the possible isomers is listed below. That doesn't rule out the connections optionally in the form of the isomer mixtures or in the other isomeric form.
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-5 A-a) bis (I-5 A-g) sowie (I-5 B-a) bis (I-5 B-g), wenn Z für die Gruppe (5) steht, Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-5 Aa) to (I- 5 Ag) and (I-5 Ba) to (I-5 Bg), if Z represents group (5),
worin A, D, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenenwherein A, D, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n are those given above
Bedeutungen besitzen.
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-6 A-a) bis (I-6 A-g) sowie (I-6 B-a) bis (I-6 B-g), wenn Z für die Gruppe (6) steht, Have meanings. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-6 Aa) to (I- 6 Ag) and (I-6 Ba) to (I-6 Bg), if Z stands for group (6),
worin wherein
A, E, L, M, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenenA, E, L, M, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n the above
Bedeutungen besitzen Die Verbindungen der Formel (I-7) können in Abhängigkeit von der Stellung desHave meanings The compounds of formula (I-7) can, depending on the position of
Substituenten G in den zwei isomeren Formen der Formeln (I-7)a und (I-7)b vorliegen,
There are substituents G in the two isomeric forms of the formulas (I-7) a and (I-7) b ,
was durch die gestrichelte Linie in der Formel (I-7) zum Ausdruck gebracht werden soll. Die Verbindungen der Formeln (I-7)a und (I-7)b können sowohl als Gemische als auch in Form ihrer reinen Isomeren vorliegen. Gemische der Verbindungen der Formeln (I-7)a und (I-7)b lassen sich gegebenenfalls in an sich bekannter Weise durch physikalische Methoden trennen, beispielsweise durch chromatographische Methoden. Aus Gründen der besseren Übersichtlichkeit wird im folgenden jeweils nur eines der möglichen Isomeren aufgeführt. Das schließt nicht aus, daß die Verbindungen gegebenenfalls in Form der Isomerengemische oder in der anderen isomeren Form vorliegen können. which is to be expressed by the broken line in formula (I-7). The compounds of the formulas (I-7) a and (I-7) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-7) a and (I-7) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods. For reasons of better clarity, only one of the possible isomers is listed below. This does not exclude that the compounds may optionally be in the form of the isomer mixtures or in the other isomeric form.
Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (f) und (g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-7 A-a) bisIncluding the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-7 A-a) to result
(I-7 A-g) sowie (I-7 B-a) bis (I-7 B-g), wenn Z für die Gruppe (7) steht, (I-7 A-g) and (I-7 B-a) to (I-7 B-g) when Z represents group (7),
worin wherein
A, B, D, E, L, M, Q1, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenen Bedeutungen besitzen A, B, D, E, L, M, Q 1 , X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above
Die Verbindungen der Formel (I-8) können in Abhängigkeit von der Stellung des Substituenten G in den zwei isomeren Formen der Formeln (I-8)a und (I-8)b vorliegen, Depending on the position of the substituent G, the compounds of the formula (I-8) can exist in the two isomeric forms of the formulas (I-8) a and (I-8) b ,
was durch die gestrichelte Linie in der Formel (I-8) zum Ausdruck gebracht werden soll
Die Verbindungen der Formeln (I-8)a und (I-8)b können sowohl als Gemische als auch in Form ihrer reinen Isomeren vorliegen. Gemische der Verbindungen der Formeln (I-8)a und (I-8)b lassen sich gegebenenfalls in an sich bekannter Weise durch physikalische Methoden trennen, beispielsweise durch chromatographische Methoden. which is to be expressed by the dashed line in formula (I-8) The compounds of the formulas (I-8) a and (I-8) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-8) a and (I-8) b can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
Aus Gründen der besseren Übersichtlichkeit wird im folgenden jeweils nur eines der möglichen Isomeren aufgeführt. Das schließt nicht aus, daß die Verbindungen gegebenenfalls in Form der Isomerengemische oder in der anderen isomeren Form vorliegen können. Unter Einbeziehung der verschiedenen Bedeutungen (a), (b), (c), (d), (e), (0 undFor reasons of better clarity, only one of the possible isomers is listed below. This does not exclude that the compounds may optionally be in the form of the isomer mixtures or in the other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (0 and
(g) der Gruppe G ergeben sich folgende hauptsächliche Strukturen (I-8 A-a) bis (I-8 A-g) sowie (I-8 B-a) bis (I-8 B-g), wenn Z für die Gruppe (8) steht, (g) of group G the following main structures result (I-8 A-a) to (I-8 A-g) and (I-8 B-a) to (I-8 B-g), if Z stands for group (8),
(I-8 (I-8
worin wherein
A, B, D, E, L, M, Q1, Q2, Q3, X, R1, R2, R3, R4, R5, R6, R7 und n die oben angegebenen Bedeutungen besitzen. A, B, D, E, L, M, Q 1 , Q 2 , Q 3 , X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above .
Weiterhin wurde gefunden, daß man die Verbindungen der Formel (I) nach einem der im folgenden beschriebenen Verfahren erhält: It has also been found that the compounds of the formula (I) can be obtained by one of the processes described below:
(A) Man erhält 3-Thienylpyrrolidin-2,4-dione bzw. deren Enole der Formel (I-1-a) (A) 3-thienylpyrrolidine-2,4-diones or their enols of the formula (I-1-a)
in welcher in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, wenn man A, B, D, X and n have the meanings given above if one
N-Acylaminosäureester der Formel (II)
N-acylamino acid esters of the formula (II)
in welcher in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, und A, B, D, X and n have the meanings given above, and
R8 für Alkyl, bevorzugt C1-C6-Alkyl steht, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular kondensiert. R 8 represents alkyl, preferably C 1 -C 6 alkyl, intramolecularly condensed in the presence of a diluent and in the presence of a base.
(B) Außerdem wurde gefunden, daß man 3-Thienyl-4-hydroxy-Δ3-dihydrofuranon-Derivate der Formel (I-2-a) (B) It was also found that 3-thienyl-4-hydroxy-Δ 3 -dihydrofuranone derivatives of the formula (I-2-a)
in welcher in which
A, B, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man A, B, X and n have the meanings given above, if one
Carbonsäureester der Formel (III)
in welcher Carboxylic acid esters of formula (III) in which
A, B, X, R8 und n die oben angegebenen Bedeutungen haben, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular kondensiert. A, B, X, R 8 and n have the meanings given above, condensed intramolecularly in the presence of a diluent and in the presence of a base.
(C) Weiterhin wurde gefunden, daß man 3-Thienyl-4-hydroxy-Δ3-dihydrothiophenon-Derivate der Formel (I-3-a) (C) It was also found that 3-thienyl-4-hydroxy-Δ 3 -dihydrothiophenone derivatives of the formula (I-3-a)
in welcher A, B, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man ß-Ketocarbonsäureester der Formel (IV) in which A, B, X and n have the meanings given above, is obtained if β-ketocarboxylic acid esters of the formula (IV)
in welcher
A, B, X, R8 und n die oben angegebenen Bedeutungen haben und in which A, B, X, R 8 and n have the meanings given above and
W für Wasserstoff, Halogen, Alkyl, bevorzugt C1-C6-Alkyl, oder Alkoxy, bevorzugt C1-C8-Alkoxy, steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Säure intramolekular cyclisiert. W represents hydrogen, halogen, alkyl, preferably C 1 -C 6 -alkyl, or alkoxy, preferably C 1 -C 8 -alkoxy, optionally cyclized intramolecularly in the presence of a diluent and in the presence of an acid.
(D) Man erhält 3-Hydroxy-4-thienyl-5-oxo-pyrazoline der Formel (I-4-a) (D) 3-Hydroxy-4-thienyl-5-oxopyrazoline of the formula (I-4-a) is obtained
in welcher in which
A, D, X und n die oben angegebenen Bedeutungen haben, wenn man A, D, X and n have the meanings given above, if one
(α) Halogencarbonylketene der Formel (V) (α) halocarbonyl ketene of the formula (V)
in welcher in which
X und n die oben angegebenen Bedeutungen haben und
Hal für Halogen, insbesondere Chlor oder Brom steht, oder (ß) Malonsäurederivate der Formel (VI) X and n have the meanings given above and Hal represents halogen, in particular chlorine or bromine, or (β) malonic acid derivatives of the formula (VI)
in welcher in which
R8, X und n die oben angegebenen Bedeutungen haben, mit Hydrazinen der Formel (VII) R 8 , X and n have the meanings given above, with hydrazines of the formula (VII)
A-NH-NH-D (VII) in welcher A und D die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base umsetzt. A-NH-NH-D (VII) in which A and D have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base.
(E) Weiterhin wurde gefunden, daß man die neuen 3-Thienylpyron-Derivate der Formel (I-5-a) (E) It was also found that the new 3-thienylpyrone derivatives of the formula (I-5-a)
in welcher
A, D, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Carbonylverbindungen der Formel (VIII) in which A, D, X and n have the meanings given above, if carbonyl compounds of the formula (VIII)
in welcher in which
A und D die oben angegebenen Bedeutungen haben, mit Ketensäurehalogeniden der Formel (V) A and D have the meanings given above, with ketene acid halides of the formula (V)
in welcher X und n die oben angegebenen Bedeutungen haben und in which X and n have the meanings given above and
Hal für Halogen, vorzugsweise für Chlor oder Brom, steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säureakzeptors umsetzt. Hal represents halogen, preferably chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
(F) Weiterhin wurde gefunden, daß man die neuen Thienyl-1,3-thiazin-Derivate der Formel (I-6-a) (F) It was also found that the new thienyl-1,3-thiazine derivatives of the formula (I-6-a)
in welcher in which
A, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Thioamide der Formel (IX) A, X and n have the meanings given above, is obtained if thioamides of the formula (IX)
in welcher in which
A die oben angegebene Bedeutung hat, mit Ketensäurehalogeniden der Formel (V) A has the meaning given above, with ketene acid halides of the formula (V)
in welcher in which
Hal, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säureakzeptors umsetzt. Weiterhin wurden gefunden, daß man 2-Thienyl-3-hydroxy-Δ2-cyclopenten- 1-on-Derivate der Formel (I-7-a) Hal, X and n have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor. It was also found that 2-thienyl-3-hydroxy-Δ 2 -cyclopenten-1-one derivatives of the formula (I-7-a)
in welcher
A, B, D, Q1, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Ketocarbonsäureester der Formel (X) in which A, B, D, Q 1 , X and n have the meanings given above, is obtained if ketocarboxylic acid esters of the formula (X)
(X)
(X)
in welcher in which
A, B, D, R , Q1, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular cyclisiert. A, B, D, R, Q 1 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base.
(H) Weiterhin wurde gefunden, daß man 2-Thienyl-3-hydroxy-Δ2-cyclohexen-1 - on-Derivate der Formel (I-8-a) (H) It was also found that 2-thienyl-3-hydroxy-Δ 2 -cyclohexen-1 - one derivatives of the formula (I-8-a)
in welcher in which
A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, if
Ketocarbonsäureester der Formel (XI)
in welcher Ketocarboxylic acid esters of the formula (XI) in which
A, B, D, Q1, Q2, Q3, R8, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular cyclisiert. A, B, D, Q 1 , Q 2 , Q 3 , R 8 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base.
Außerdem wurde gefunden, It was also found
(I) daß man die Verbindungen der oben gezeigten Formeln (I-1-b) bis (I-8-b), in welchen A, B, D, Q1, Q2, Q3, R1, X und n die oben angebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten(I) that the compounds of the formulas (I-1-b) to (I-8-b) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , R 1 , X and n have the meanings given above, is obtained by compounds of the ones shown above
Formeln (I-1-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, jeweils α) mit Säurehalogeniden der Formel (XII)
Formulas (I-1-a) to (I-8-a), in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each α) with acid halides of the formula (XII)
in welcher in which
R1 die oben angegebene Bedeutung hat und R 1 has the meaning given above and
Hal für Halogen, insbesondere Chlor oder Brom steht oder ß) mit Carbonsäureanhydriden der Formel (XIII) R1-CO-O-CO-R1 (XIII)
in welcher Hal represents halogen, in particular chlorine or bromine, or β) with carboxylic anhydrides of the formula (XIII) R 1 -CO-O-CO-R 1 (XIII) in which
R1 die oben angegebene Bedeutung hat, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt; (J) daß man die Verbindungen der oben gezeigten Formeln (I-1-c) bis (I-8-c), in welchen A, B, D, Q1, Q2, Q3, R2, M, X und n die oben angegebenen Bedeutungen haben und L für Sauerstoff steht, erhält, wenn man Verbindungen der oben gezeigten Formeln (I-1-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, jeweils mit Chlorameisensäureestern oder Chlorameisensäurethioestern der FormelR 1 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; (J) that the compounds of the formulas (I-1-c) to (I-8-c) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , R 2 , M, X and n has the meanings given above and L represents oxygen, is obtained if compounds of the formulas (I-1-a) to (I-8-a) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each with chloroformate or chloroformate thioester of the formula
(XIV) (XIV)
R2-M-CO-CI (XIV) in welcher R2 und M die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt; R 2 -M-CO-CI (XIV) in which R 2 and M have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
(K) daß man Verbindungen der oben gezeigten Formeln (I-1-c) bis (I-8-c), in welchen A, B, D, Q1, Q2, Q3, R2, M, X und n die oben angegebenen Bedeutungen haben und L für Schwefel steht, erhält, wenn man Verbindungen der oben gezeigten Formeln (I-1-a) bis (I-8-a), in welchen A, B,(K) that compounds of the formulas (I-1-c) to (I-8-c) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , R 2 , M, X and n has the meanings given above and L represents sulfur, is obtained if compounds of the formulas (I-1-a) to (I-8-a) shown above, in which A, B,
D, Q1, Q", Q3, X und n die oben anngegebenen Bedeutungen haben, jeweils α) mit Chlormonothioameisensäureestern oder Chlordithioameisensäureestern der Formel (XV)
in welcher D, Q 1 , Q ", Q 3 , X and n have the meanings given above, in each case α) with chloromothio formic acid esters or chlorodithio formic acid esters of the formula (XV) in which
M und R2 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt oder ß) mit Schwefelkohlenstoff und anschließend mit Alkylhalogeniden der Formel (XVI) M and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder or ß) with carbon disulfide and then with alkyl halides of the formula (XVI)
R2-Hal (XVI) in welcher R 2 -Hal (XVI) in which
R2 die oben angegebene Bedeutung hat und R 2 has the meaning given above and
Hal für Chlor, Brom oder Iod steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base umsetzt, (L) daß man Verbindungen der oben gezeigten Formeln (I-1-d) bis (I-8-d), in welchen A, B, D, Q1, Q2, Q3, R3, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formeln (I-I-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, jeweils mit Sulfonsaurechloriden der Formel (XVII) Hal represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a base, (L) that compounds of the formulas (I-1-d) to (I-8-d) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , R 3 , X and n have the meanings given above, is obtained if compounds of the formulas (IIa) to (I-8-a) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, in each case with sulfonyl chlorides of the formula (XVII)
R3-SO2-Cl (XVII)
in welcher R3 die oben angegebene Bedeutung hat, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt, (M) daß man Verbindungen der oben gezeigten Formeln (I-1-e) bis (I-8-e), in welchen A, B, D, Q1, Q2, Q3, L, R4, R5, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formeln (I-1-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, jeweils mit Phosphorverbindungen der Formel (XVIII) R 3 -SO 2 -Cl (XVII) in which R 3 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, (M) that compounds of the formulas (I-1-e) to (I-8-e) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , L, R 4 , R 5 , X and n have the meanings given above, is obtained if compounds of the formulas (I-1-a) shown above to (I-8-a), in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each with phosphorus compounds of the formula (XVIII)
in welcher in which
L, R4 und R5 die oben angegebenen Bedeutungen haben und L, R 4 and R 5 have the meanings given above and
Hal für Halogen, insbesondere Chlor oder Brom steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt, Hal represents halogen, in particular chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(N) daß man Verbindungen der oben gezeigten Formeln (I-1-f) bis (I-8-f), in welchen A, B, D, Q1, Q2, Q3, E, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der Formeln (I-1-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen(N) that compounds of the formulas (I-1-f) to (I-8-f) shown above, in which A, B, D, Q 1 , Q 2 , Q 3 , E, X and n the above have the meanings given, is obtained if compounds of the formulas (I-1-a) to (I-8-a) in which A, B, D, Q 1 , Q 2 , Q 3 , X and n are those given above
Bedeutungen haben, jeweils mit Metallverbindungen oder Aminen der Formeln (XIX) oder (XX)
Me(OR10)t (XIX)Have meanings, in each case with metal compounds or amines of the formulas (XIX) or (XX) Me (OR 10 ) t (XIX)
in welchen in which
Me für ein ein- oder zweiwertiges Metall, bevorzugt ein Alkali- oder Erdalkalimetall wie Lithium, Natrium, Kalium, Magnesium oder Calcium, t für die Zahl 1 oder 2 und Me for a mono- or divalent metal, preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium, t for the number 1 or 2 and
R10, R11, R12 unabhängig voneinander für Wasserstoff oder Alkyl, bevorzugt C1-C8- Alkyl, stehen, gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, O) daß man Verbindungen der oben gezeigten Formeln (I-1-g) bis (I-8-g), in welchen A, B, D, Q1, Q2, Q3, L, R6, R7, X und n die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formeln (I-1-a) bis (I-8-a), in welchen A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, jeweils α) mit Isocyanaten oder Isothiocyanaten der Formel (XXI) R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl, preferably C 1 -C 8 alkyl, optionally reacted in the presence of a diluent, O) that compounds of the formulas (I-1-g) shown above to (I-8-g) in which A, B, D, Q 1 , Q 2 , Q 3 , L, R 6 , R 7 , X and n have the meanings given above, if compounds of the ones shown above are obtained Formulas (I-1-a) to (I-8-a), in which A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above, each α) with isocyanates or isothiocyanates of the formula (XXI)
R6-N=C=L (XXI) in welcher R 6 -N = C = L (XXI) in which
R6 und L die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators umsetzt oder ß) mit Carbamidsäurechloriden oder Thiocarbamidsäurechloriden der Formel (XXII)
R 6 and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or ß) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XXII)
in welcher in which
L, R6 und R7 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Saurebindemittels, umsetzt L, R 6 and R 7 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
Weiterhin wurde gefunden, daß die neuen substituierten Thiophenderivate der Formel (I) eine sehr gute Wirksamkeit als Schädlingsbekämpfungsmittel, vorzugsweise als Insektizide, Akarizide, Nematizide und Herbizide sowie als Ektoparasitizide aufweisen Die erfindungsgemäßen substituierten Thiophenderivate sind durch die Formel (I) allgemein definiert Bevorzugte Substituenten bzw. Bereiche der in der oben und nachstehend erwähnten Formeln aufgeführten Reste werden im folgenden erläutert Furthermore, it was found that the new substituted thiophene derivatives of the formula (I) have very good activity as pesticides, preferably as insecticides, acaricides, nematicides and herbicides and as ectoparasiticides. The substituted thiophene derivatives according to the invention are generally defined by the formula (I). Preferred substituents or Ranges of the radicals listed in the formulas mentioned above and below are explained below
X steht bevorzugt für Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, C1-C6-HalogenalkyI, C1-C6-Halogenalkoxy, Nitro oder Cyano X preferably represents halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 -HalogenalkyI, C 1 -C 6 haloalkoxy, nitro or cyano
oder zwei Substituenten X bilden gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gesattigten oder ungesättigten, gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl, C1- C6-Halogenalkoxy, Nitro oder Cyano substituierten 5- bis 8-gliedrigen Carbocyclus n steht bevorzugt für 1, 2 oder 3 Z steht bevorzugt für eine der Gruppen or two substituents X together with the carbon atoms to which they are attached form a saturated or unsaturated, optionally by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 - C 6 haloalkoxy, nitro or cyano substituted 5- to 8-membered carbocycle n preferably represents 1, 2 or 3 Z preferably represents one of the groups
steht bevorzugt für Wasserstoff oder jeweils gegebenenfalls durch Halogen substituiertes C1-C12-Alkyl, C2-C8-Alkenyl, C1-C10-Alkoxy-C1-C8-alkyl, Poly-C1-C8-alkoxy-C1-C8-alkyl, C1-C10-Alkylthio-C1-C6-alkyl, gegebenenfalls durch C1-C6-Alkyl, Halogen oder C1-C6-Alkoxy substituiertes Cycloalkyl mit 3 bis 8 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, oder für jeweils gegebenenfalls durch Halogen, C1-C8-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder Nitro substituiertes C6- oder C10- Aryl, Hetaryl mit 5 bis 6 Ringatomen und ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel oder C6- oder C10-Aryl-C1- C6-alkyl preferably represents hydrogen or in each case optionally substituted by halogen C 1 -C 12 alkyl, C 2 -C 8 alkenyl, C 1 -C 10 alkoxy-C 1 -C 8 alkyl, poly-C 1 -C 8 - alkoxy-C 1 -C 8 alkyl, C 1 -C 10 alkylthio-C 1 -C 6 alkyl, optionally substituted by C 1 -C 6 alkyl, halogen or C 1 -C 6 alkoxy cycloalkyl with 3 to 8 ring atoms, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, or for each optionally by halogen, C 1 -C 8 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 - Alkoxy or nitro substituted C 6 - or C 10 - aryl, hetaryl with 5 to 6 ring atoms and one to three heteroatoms from the series nitrogen, oxygen and sulfur or C 6 - or C 10 -aryl-C 1 - C 6 -alkyl
B steht bevorzugt für Wasserstoff, C1-C12-Alkyl oder C1-C8-Alkoxy-C1-C8- alkyl oder A, B und das Kohlenstoffatom an das sie gebunden sind, stehen bevorzugt für einen gesattigten oder ungesättigten C3-C10-Spirocyclus, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und der gegebenenfalls durch C1-
C8-Alkyl, C3-C10-Cycloalkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy, C1-C8- Alkylthio, Halogen oder Phenyl substituiert ist oder B preferably represents hydrogen, C 1 -C 12 alkyl or C 1 -C 8 -alkoxy-C 1 -C 8 - alkyl, or A, B and the carbon atom to which they are attached preferably represent a saturated or unsaturated C 3 -C 10 spirocycle, in which one or two methylene groups which are not directly adjacent are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C 1 - C 8 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, halogen or phenyl or is substituted
A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen bevorzugt für einen C3-C6-Spirocyclus, der durch eine gegebenenfalls durch ein oder zwei Sauerstoff- und/oder Schwefelatome unterbrochenen Alkylendiyl-, oder durch einen Alkylendioxyl- oder durch eine Alkylendithioyl-Gruppe substituiert ist, die mit dem Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis achtgliedrigen Spirocyclus bildet oder A, B and the carbon atom to which they are attached preferably represent a C 3 -C 6 spirocycle, which is interrupted by an alkylenediyl, or by an alkylenedioxyl or optionally interrupted by one or two oxygen and / or sulfur atoms an alkylenedithioyl group is substituted which forms a further five- to eight-membered spirocycle with the carbon atom to which it is attached, or
A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen bevorzugt für einen C3-C8-Spirocyclus, bei dem zwei Substituenten gemeinsam für einen gegebenenfalls durch C1-C6-Alkyl, C1-C6-Alkoxy oder Halogen substituierten gesättigten oder einfach oder mehrfach ungesättigten 5- bis 8-gliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoff- oder Schwefelatom enthält. D steht bevorzugt für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes C1-C12-Alkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, C1-C10-Alkoxy- C2-C8-alkyl, Poly-C1-C8-alkoxy-C2-C8-alkyl, C1-C10-Alkylthio-C2-C8-alkyl, gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Alkoxy oder C1-C4- Halogenalkyl substituiertes Cycloalkyl mit 3 bis 8 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylenngruppen durch Sauerstoff und/oder Schwefel ersetzt sind oder jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder Nitro substituiertes Phenyl, Hetaryl mit 5 bis 6 Ringatomen und ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel oder Phenyl-C1-C6-alkyl oder A, B and the carbon atom to which they are attached are preferably a C 3 -C 8 -spirocycle, in which two substituents together for one optionally by C 1 -C 6 alkyl, C 1 -C 6 alkoxy or Halogen substituted saturated or mono- or polyunsaturated 5- to 8-membered cycle, which optionally contains an oxygen or sulfur atom. D preferably represents hydrogen, in each case optionally substituted by halogen C 1 -C 12 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 10 alkoxy-C 2 -C 8 alkyl , Poly-C 1 -C 8 alkoxy-C 2 -C 8 alkyl, C 1 -C 10 alkylthio-C 2 -C 8 alkyl, optionally by halogen, C 1 -C 4 alkyl, C 1 - C 4 alkoxy or C 1 -C 4 haloalkyl-substituted cycloalkyl having 3 to 8 ring atoms, in which one or two non-directly adjacent methyl groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or nitro substituted phenyl, hetaryl with 5 to 6 ring atoms and one to three heteroatoms from the series nitrogen, oxygen and sulfur or phenyl-C 1 -C 6 alkyl or
A und D stehen bevorzugt gemeinsam mit den Atomen, an die sie gebunden sind, für eine gegebenenfalls einfach bis vierfach, gleich oder verschieden substituierte Alkandiyl- oder Alkendiylgruppierung mit 3 bis 6 Kohlenstoffatomen, A and D, together with the atoms to which they are attached, preferably represent an alkanediyl or alkenediyl group having 3 to 6 carbon atoms which may be monosubstituted to tetrasubstituted in the same way or differently,
worin a) gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und wobei als Substituenten in Frage kommen.
Halogen, Hydroxy, Mercapto oder jeweils gegebenenfalls durch Halogen substituiertes C1-C10-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthιo, C3-C7- Cycloalkyl, Phenyl oder Benzyloxy, wherein a) optionally one or two non-directly adjacent methylene groups are replaced by oxygen and / or sulfur and are suitable as substituents. Halogen, hydroxy, mercapto or in each case optionally substituted by halogen C 1 -C 10 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 3 -C 7 cycloalkyl, phenyl or benzyloxy,
oder eine weitere Alkandiylgruppierung mit 3 bis 6 Kohlenstoffatomen, die gegebenenfalls durch C1-C6-Alkyl substituiert ist oder in der gegebenenfalls zwei benachbarte Substituenten mit den Kohlenstoffatomen, an die sie gebunden sind, einen weiteren gesattigten oder ungesättigten C5-C6-Cyclus bilden, or a further alkanediyl grouping with 3 to 6 carbon atoms, which is optionally substituted by C 1 -C 6 -alkyl or in which two adjacent substituents with the carbon atoms to which they are attached optionally contain a further saturated or unsaturated C 5 -C 6 - Form a cycle,
oder die b) gegebenenfalls durch eine der nachfolgenden Gruppierungen or b) optionally by one of the following groupings
unterbrochen ist is interrupted
Q1, Q2, Q3 stehen unabhängig voneinander bevorzugt für Wasserstoff oder gegebenenfalls durch Halogen substituiertes C1-C6-Alkyl oder Q 1 , Q 2 , Q 3 , independently of one another, preferably represent hydrogen or C 1 -C 6 alkyl or optionally substituted by halogen
B und Q1 stehen gemeinsam bevorzugt für eine C1-C6-Alkandiylgruppierung, die gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiert ist B and Q 1 together preferably represent a C 1 -C 6 -alkanediyl group which is optionally substituted by halogen or C 1 -C 6 -alkyl
G steht bevorzugt für Wasserstoff (a) oder für eine der Gruppen
in welchen G preferably represents hydrogen (a) or one of the groups in which
E für ein Metallionäquivalent oder ein Ammoniumion steht, E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht und M für Sauerstoff oder Schwefel steht. steht bevorzugt für jeweils gegebenenfalls durch Halogen substituiertes C1-C20-Alkyl, C2-C20-Alkenyl, C1-C8-AIkoxy-C1-C8-aIkyl, C1-C8-Alkylthio-C1-C8-alkyl, Poly-C1-C8-alkoxy-C1-C8-alkyl oder gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes Cycloalkyl mit 3 bis 8 Ringatomen, in welchem gegebenenfalls eine oder zwei nicht direkt benachbarteL stands for oxygen or sulfur and M stands for oxygen or sulfur. preferably represents in each case optionally substituted by halogen C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio-C 1 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 1 -C 8 alkyl or optionally substituted by halogen or C 1 -C 6 alkyl cycloalkyl having 3 to 8 ring atoms, in which one or two may not directly neighboring
Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, für gegebenenfalls durch Halogen, Nitro, C1-C6-Alkyl, C1-C6-Alkoxy, C1- C6-Halogenalkyl, C1-C6-Halogenalkoxy, C1-C6-Alkylthio oder C1-C6-Alkylsulfonyl substituiertes Phenyl, für gegebenenfalls durch Halogen, C1-C6- Alkyl, C1-C8-Alkoxy, C1-C6- Halogenalkyl oder C1-C6-Halogenalkoxy substituiertes Phenyl-C1-C6-alkyl, für gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes 5- oder 6-gliedriges Hetaryl mit ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel, für gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes Phenoxy- C1-C6-alkyl oder
für gegebenenfalls durch Halogen, Amino oder C1-C8-Alkyl substituiertes 5- oder 6-gliedriges Hetaryloxy-C1-C6-alkyl mit ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel. Methyl groups are replaced by oxygen and / or sulfur, optionally substituted by halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 - C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl substituted phenyl, optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkyl or C 1 -C 6 -Halogenalkoxy substituted phenyl-C 1 -C 6 -alkyl, for 5- or 6-membered hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl with one to three heteroatoms from the series nitrogen, oxygen and sulfur, for optionally by halogen or C 1 -C 6 -alkyl-substituted phenoxy-C 1 -C 6 alkyl, or for 5- or 6-membered hetaryloxy-C 1 -C 6 alkyl optionally substituted by halogen, amino or C 1 -C 8 alkyl and having one to three heteroatoms from the series consisting of nitrogen, oxygen and sulfur.
R2 steht bevorzugt für jeweils gegebenenfalls durch Halogen substituiertes C1- C20-Alkyl, C3-C20-Alkenyl, C1-C8-Alkoxy-C1-C8-alkyl oder Poly-C1-C8- alkoxy-C1-C8-alkyl, für gegebenenfalls durch Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes C3-C8-Cycloalkyl, oder für jeweils gegebenenfalls durch Halogen, Nitro, C1-C6-Alkyl, C1-C8-Alkoxy oder C1-C6-Halogenalkyl substituiertes Phenyl oder Benzyl R 2 preferably represents in each case optionally substituted by halogen C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or poly-C 1 -C 8 - alkoxy-C 1 -C 8 alkyl, for C 3 -C 8 cycloalkyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, or for each optionally substituted by halogen, nitro, C 1 -C 6 alkyl, C 1 -C 8 alkoxy or C 1 -C 6 haloalkyl substituted phenyl or benzyl
RJ' steht bevorzugt für gegebenenfalls durch Halogen substituiertes C1-C8- Alkyl oder für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6- Alkoxy, C1-C3-Halogenalkyl, C1-C3-Halogenalkoxy, Nitro oder Cyano substituiertes Benzyl oder Phenyl. R4 und R3 stehen bevorzugt unabhängig voneinander für gegebenenfalls durchR J 'preferably represents C 1 -C 8 alkyl optionally substituted by halogen or in each case optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro or cyano substituted benzyl or phenyl. R 4 and R 3 are preferably, independently of one another, optionally
Halogen substituiertes C1-C8-Alkyl, C1-C8-Alkoxy, C1-C8-Alkylamino, Di- (C1-C8-alkyl)-amino, C1-C8-Alkylthio, C2-C8-Alkenylthio, C3-C7-Cycloalkylthio oder für jeweils gegebenenfalls durch Halogen, Nitro, Cyano, C1- C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkyl oder C1-C4-Halogenalkyl substituiertes Phenyl, Phenoxy oder Phenylthio. Halogen substituted C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylamino, di (C 1 -C 8 alkyl) amino, C 1 -C 8 alkylthio, C 2 -C 8 -alkenylthio, C 3 -C 7 -cycloalkylthio or represents in each case optionally substituted by halogen, nitro, cyano, C 1 - C 4 alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl substituted phenyl, phenoxy or phenylthio.
R6 und R7 stehen unabhängig voneinander bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl, C3-C8-Cycloalkyl, C1-C8-Alkoxy, C3-C8-Alkenyl, C1-C8-Alkoxy-C1-C8-alkyl, für gegebenenfalls durch Halogen, C1-C8-Halogenalkyl, C1-C8-Alkyl oder C1-C8-Alkoxy substituiertes Phenyl, gegebenenfalls durch Halogen, C1-C8-Alkyl, C1- C8-Halogenalkyl oder C1-C8-Alkoxy substituiertes Benzyl oder zusammen für C3-C6-Alkandiyl, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist.
R13 steht bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl, C1-C8-Alkoxy oder C3-C8-Cycloalkyl oder für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-AIkoxy, C1-C3- Halogenalkyl, C1-C3-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl. R 6 and R 7 independently of one another preferably represent hydrogen, in each case optionally substituted by halogen C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, for phenyl optionally substituted by halogen, C 1 -C 8 haloalkyl, C 1 -C 8 alkyl or C 1 -C 8 alkoxy, optionally substituted by halogen , C 1 -C 8 alkyl, C 1 - C 8 haloalkyl or C 1 -C 8 -alkoxy-substituted benzyl or together represent C 3 -C 6 -alkanediyl in which optionally one methylene group is replaced by oxygen or sulfur. R 13 preferably represents hydrogen, in each case optionally substituted by halogen C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy or C 3 -C 8 -cycloalkyl or for in each case optionally by halogen, C 1 -C 6 -alkyl , C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro or cyano substituted phenyl or benzyl.
R14 und R15 stehen bevorzugt unabhängig voneinander für Wasserstoff, C1-C8- Alkyl, C1-C8-Halogenalkyl, C3-C6-Cycloalkyl, für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C3-HalogenaIkyl, C1-C3- Halogenalkoxy, Cyano oder Nitro substituiertes Phenyl oder Benzyl oder gemeinsam für eine gegebenenfalls durch C1-C4-Alkyl substituierte C4-C6- Alkandiylgruppe. R 14 and R 15 are preferably independently of one another hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 6 cycloalkyl, each in each case optionally by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 -HalogenaIkyl, C 1 -C 3 - halogenoalkoxy, cyano or nitro-substituted phenyl or benzyl or together represent an optionally C 1 -C 4 alkyl substituted C 4 -C 6 - alkanediyl group.
R16 und R17 sind gleich oder verschieden und stehen bevorzugt für C1-C6-Alkyl oder R 16 and R 17 are the same or different and are preferably C 1 -C 6 alkyl or
R16 und R17 stehen gemeinsam bevorzugt für einen C2-C4-Alkandiylrest, der gegebenenfalls durch C1-C8-Alkyl oder durch gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl substituiert ist. R 16 and R 17 together preferably represent a C 2 -C 4 -alkanediyl radical which may be substituted by C 1 -C 8 -alkyl or by optionally halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl.
R18 und R19 stehen unabhängig voneinander bevorzugt für Wasserstoff, gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl oder gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C4-Halogenalkyl, C1-C4- Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl. R 18 and R 19 independently of one another preferably represent hydrogen, optionally substituted by halogen C 1 -C 8 -alkyl or optionally by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 - Haloalkyl, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl.
R20 und R21 stehen unabhängig voneinander bevorzugt für C1-C10-Alkyl, C3-C10- Alkenyl, C1-C10-Alkoxy, C1-C10-Alkylamino, C3-C10-Alkenylamino, Di- (C1-C10-alkyl)-amino oder Di-(C3-C10-alkenyl)-amino. X steht besonders bevorzugt für Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4- Alkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy, Nitro oder Cyano R 20 and R 21 independently of one another preferably represent C 1 -C 10 alkyl, C 3 -C 10 alkenyl, C 1 -C 10 alkoxy, C 1 -C 10 alkylamino, C 3 -C 10 alkenylamino, Di (C 1 -C 10 alkyl) amino or di (C 3 -C 10 alkenyl) amino. X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 - alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 -haloalkoxy , Nitro or cyano
oder zwei Substituenten X bilden gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy,
Nitro oder Cyano substituierten ungesättigten 5- bis 7-gliedrigen Carbocyclus. n steht besonders bevorzugt für 1, 2 oder 3. or two substituents X together with the carbon atoms to which they are attached form one, optionally by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, Nitro or cyano substituted unsaturated 5- to 7-membered carbocycle. n particularly preferably represents 1, 2 or 3.
Z steht besonders bevorzugt für eine der Gruppen Z particularly preferably represents one of the groups
steht besonders bevorzugt für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C10-Alkyl, C2-C6-Alkenyl, C1-C8- Alkoxy-C1-C6-alkyl, Poly-C1-C6-alkoxy-C1-C6-alkyl, C1-C8-Alkylthio-C1- C6-alkyl, gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkoxy, Fluor oder Chlor substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, oder jeweils gegebenenfalls
durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder Nitro substituiertes Phenyl, Furanyl, Pyridyl, Imidazolyl, Triazolyl, Pyrazolyl, Indolyl, Thiazolyl, Thienyl oder Phenyl-C1-C4-alkyl. particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 10 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, poly-C 1 - C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 8 alkylthio-C 1 - C 6 alkyl, optionally by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, fluorine or chlorine substituted cycloalkyl having 3 to 7 ring atoms, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, or in each case if appropriate phenyl substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or nitro, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-C 1 -C 4 alkyl.
B steht besonders bevorzugt für Wasserstoff, C1-C10-Alkyl oder C1-C6- Alkoxy-C1-C4-alkyl oder B particularly preferably represents hydrogen, C 1 -C 10 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl or
A, B und das Kohlenstoffatom an das sie gebunden sind, stehen besonders bevorzugt für einen gesättigten oder ungesättigten C3-C9-Spirocyclus, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und der gegebenenfalls durch C1-C6-Alkyl, C3-C8-Cycloalkyl, C1-C3-Halogenalkyl, C1-C6-AIkoxy, C1-C6-Alkylthio, Fluor, Chlor oder Phenyl substituiert ist oder A, B and the carbon atom to which they are attached are particularly preferably a saturated or unsaturated C 3 -C 9 spirocycle, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C. 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, fluorine, chlorine or phenyl or substituted
A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen besonders bevorzugt für einen C3-C6-Spirocyclus, der durch eine gegebenenfalls durch ein oder zwei Sauerstoff- oder Schwefelatome unterbrochenen Alkylendiyl- oder durch eine Alkylendioxyl- oder durch eine AI kylendithiol-Gruppe substituiert ist, die mit dem Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis siebengliedrigen Spirocyclus bildet oder A, B and the carbon atom to which they are attached are particularly preferably a C 3 -C 6 spirocycle, which is interrupted by an alkylene diyl or an alkylene dioxyl or by an AI which may be interrupted by one or two oxygen or sulfur atoms kylendithiol group is substituted, which forms a further five- to seven-membered spirocycle with the carbon atom to which it is attached or
A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen besonders bevorzugt für einen C3-C6-Spirocyclus, bei dem zwei Substituenten gemeinsam für einen gegebenenfalls durch C1-C5-Alkyl, C1-C5-AIkoxy, Fluor,A, B and the carbon atom to which they are attached are particularly preferably a C 3 -C 6 -spirocycle, in which two substituents together for an optionally by C 1 -C 5 alkyl, C 1 -C 5 alkoxy Fluorine
Chlor oder Brom substituierten gesättigten oder einfach oder mehrfach ungesättigten 5- oder 6-gliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoff- oder Schwefelatom enthält. Chlorine or bromine substituted saturated or mono- or polyunsaturated 5- or 6-membered cycle, which optionally contains an oxygen or sulfur atom.
D steht besonders bevorzugt für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C10-Alkyl, C3-C6-Alkenyl, C3-C6- Alkinyl, C1-C8-Alkoxy-C2-C6-alkyl, Poly-C1-C6-alkoxy-C2-C6-alkyl, C1-C8- Alkylthio-C2-C6-alkyl, gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkoxy oder C1-C2-Halogenalkyl substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind oder jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-
Alkoxy oder Nitro substituiertes Phenyl, Pyridyl, Thienyl, Furanyl, Thiazolyl, Pyrimidyl, Pyrazolyl oder Phenyl-C1-C4-alkyl oder D particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 10 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 8 -alkoxy-C 2 -C 6- alkyl, poly-C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl, C 1 -C 8 -alkylthio-C 2 -C 6 -alkyl, optionally by C 1 -C 4 -alkyl, C 1 -C 4 alkoxy or C 1 -C 2 haloalkyl-substituted cycloalkyl having 3 to 7 ring atoms, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 - Alkoxy or nitro substituted phenyl, pyridyl, thienyl, furanyl, thiazolyl, pyrimidyl, pyrazolyl or phenyl-C 1 -C 4 -alkyl or
A und D stehen besonders bevorzugt gemeinsam mit den Atomen, an die sie gebunden sind, für eine C3-C5-Alkandiyl- oder C3-C5-Alkendiylgruppierung, A and D particularly preferably together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl grouping,
worin a) gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist und welche gegebenenfalls durch Fluor, Chlor, Hydroxy, Mercapto oder durch jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C6-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C3-C6-Cycloalkyl, Phenyl oder Benzyl substituiert ist; wherein a) a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by fluorine, chlorine, hydroxy, mercapto or by C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 in each case optionally substituted by fluorine or chlorine -C 4 alkylthio, C 3 -C 6 cycloalkyl, phenyl or benzyl;
oder die b) gegebenenfalls durch eine der nachfolgenden Gruppierungen or b) optionally by one of the following groupings
unterbrochen ist; oder worin A und D im Fall von Verbindungen der Formel (I-1) gemeinsam mit den Atomen, an die sie gebunden sind, für eine der Gruppen is interrupted; or wherein A and D in the case of compounds of formula (I-1) together with the atoms to which they are attached, for one of the groups
AD-1 bis AD-20 steht. AD-1 to AD-20 stands.
Q1, Q2, Q3 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff oder gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl oder B und Q1 stehen besonders bevorzugt für eine C1-C4-Alkandiylgrυppierung, die gegebenenfalls durch Fluor, Chlor oder C1-C4-Alkyl substituiert ist. Q 1 , Q 2 , Q 3 independently of one another particularly preferably represent hydrogen or C 1 -C 4 -alkyl which is optionally substituted by fluorine or chlorine or B and Q 1 particularly preferably represent a C 1 -C 4 -alkanediyl group which may be substituted by Fluorine, chlorine or C 1 -C 4 alkyl is substituted.
G steht besonders bevorzugt für Wasserstoff (a) oder für eine der Gruppen G particularly preferably represents hydrogen (a) or one of the groups
in welchen E für ein Metallionäquivalent oder ein Ammoniumion steht, in which E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht und L represents oxygen or sulfur and
M für Sauerstoff oder Schwefel steht. M stands for oxygen or sulfur.
R1 steht besonders bevorzugt für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C16-Alkyl, C2-C16-Alkenyl, C1-C6-Alkoxy-C1-C6- alkyl, C1-C6-Alkylthio-C1-C6-alkyl, Poly-C1-C6-alkoxy-C1-C6-alkyl oder gegebenenfalls durch Fluor, Chlor oder C1-C5-Alkyl substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht
direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, für gegebenenfalls durch Fluor, Chlor, Brom, Nitro, C1-C4-Alkyl, C1-C4- Alkoxy, C1-C3-Halogenalkyl, C1-C3-Halogenalkoxy, C1-C4-Alkylthio oder C1-C4-Alkylsulfonyl substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C3-Halogenalkyl oder C1-C3-Halogenalkoxy substituiertes Phenyl-C1- C4-alkyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom oder C1-C4-Alkyl substituiertes Pyrazolyl, Thiazolyl, Pyridyl, Pyrimidyl, Furanyl oder Thienyl, für gegebenenfalls durch Fluor, Chlor, Brom oder C1-C4-Alkyl substituiertes Phenoxy-C1-C1-alkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Amino oder C1-C4- Alkyl substituiertes Pyridyloxy-C1-C5-alkyl, Pyrimidyloxy-C1-C5-alkyl oderR 1 particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 1 -C 6 alkoxy-C 1 -C 6 - alkyl, C 1 -C 6 Alkylthio-C 1 -C 6 -alkyl, poly-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or cycloalkyl having 3 to 7 ring atoms which is optionally substituted by fluorine, chlorine or C 1 -C 5 -alkyl, where one or two may not directly adjacent methylene groups are replaced by oxygen and / or sulfur, for optionally by fluorine, chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkyl, C 1 - C 3 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl substituted phenyl, for optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy substituted phenyl-C 1 - C 4 -alkyl, each for pyrazolyl, thiazolyl, pyridyl, pyrimidyl optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl, Furanyl or thienyl, for optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 alkyl phenoxy-C 1 -C 1 alkyl or for each optionally substituted by fluorine, chlorine, bromine, amino or C 1 -C 4 alkyl substituted pyridyloxy-C 1 -C 5 alkyl, pyrimidyloxy-C 1 -C 5 alkyl or
Thiazolyloxy-C1-C5-alkyl. Thiazolyloxy-C 1 -C 5 alkyl.
R2 steht besonders bevorzugt für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C16-Alkyl, C3-C16-Alkenyl, C1-C6-Alkoxy-C1-C6- alkyl oder Poly-C1-C6-alkoxy-C1-C6-alkyl, für gegebenenfalls durch Fluor, Chlor, C1-C8-Alkyl oder C1-C3-Alkoxy substituiertes C3-C7-Cycloalkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, C1-C4-Alkyl, C1-C3-Alkoxy oder C1-C8-Halogenalkyl substituiertes Phenyl oder Benzyl. R 2 particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 16 -alkyl, C 3 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or poly-C 1 - C 6 -alkoxy-C 1 -C 6 -alkyl, for C 3 -C 7 -cycloalkyl optionally substituted by fluorine, chlorine, C 1 -C 8 -alkyl or C 1 -C 3 -alkoxy or for each optionally substituted by fluorine, Chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 3 alkoxy or C 1 -C 8 haloalkyl substituted phenyl or benzyl.
R3 steht besonders bevorzugt für gegebenenfalls durch Fluor oder Chlor substituiertes C1-C6-Alkyl oder für jeweils gegebenenfalls durch Fluor,R 3 particularly preferably represents C 1 -C 6 -alkyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine,
Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C2-Halogenalkyl, C1-C2- Halogenalkoxy, Nitro oder Cyano substituiertes Benzyl oder Phenyl
R4 und R5 stehen besonders bevorzugt unabhängig voneinander für jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6- Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylthio, C3-C4-Alkenylthio, C3-C6-Cycloalkylthio oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, Cyano, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, C1-C3-Alkylthio, C1-C3-Halogenalkylthio, C1-C3-Alkyl oder C1-C3-Halogenalkyl substituiertes Phenyl, Phenoxy oder Phenylthio. Chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 - haloalkoxy, nitro or cyano substituted benzyl or phenyl R 4 and R 5 are particularly preferably independently of one another each optionally substituted by halogen C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) ) -amino, C 1 -C 6 -alkylthio, C 3 -C 4 -alkenylthio, C 3 -C 6 -cycloalkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 -alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl substituted phenyl, phenoxy or phenylthio.
R6 und R7 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1- C6-Alkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C3-C6-Alkenyl, C1-C6-Alkoxy- C1-C6-alkyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C5-Halogenalkyl, C1-C5-Alkyl oder C1-C5-Alkoxy substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C5-Alkyl, C1-C5-Halogenalkyl oder C1-C5-Alkoxy substituiertes Benzyl, oder zusammen für C3-C6-Alkandiyl, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oderR 6 and R 7 independently of one another particularly preferably represent hydrogen, represent in each case optionally substituted by fluorine, chlorine or bromine-substituted C 1 - C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 - C 6 -alkenyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, for optionally by fluorine, chlorine, bromine, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy, or together for C 3 -C 6 - Alkanediyl, wherein optionally a methylene group by oxygen or
Schwefel ersetzt ist Sulfur is replaced
R13 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durchR 13 particularly preferably represents hydrogen, in each case optionally through
Fluor oder Chlor substituiertes C1-C6-Alkyl, C1-C8-Alkoxy oder C3-C7- Cycloalkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1- C4-Alkyl, C1-C4-Alkoxy, C1-C2-Halogenalkyl, C1-C2-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl Fluorine or chlorine substituted C 1 -C 6 alkyl, C 1 -C 8 alkoxy or C 3 -C 7 cycloalkyl or for each optionally substituted by fluorine, chlorine, bromine, C 1 - C 4 alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, nitro or cyano substituted phenyl or benzyl
R14 und R15 steht besonders bevorzugt unabhängig voneinander für Wasserstoff, C1-C6-Alkyl, C1-C8-Halogenalkyl, C3-C6-Cycloalkyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C2- Halogenalkyl, C1-C2-Halogenalkoxy, Cyano oder Nitro substituiertes Phenyl oder Benzyl oder gemeinsam für eine gegebenenfalls durch C1-C3- Alkyl substituierte C4-C5-Alkandiylgruppe R 14 and R 15 are particularly preferably independently of one another hydrogen, C 1 -C 6 alkyl, C 1 -C 8 haloalkyl, C 3 -C 6 cycloalkyl, each optionally by fluorine, chlorine, bromine, C 1 - C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, cyano or nitro substituted phenyl or benzyl or together for one optionally substituted by C 1 -C 3 alkyl C 4 -C 5 alkanediyl group
R16 und R17 sind gleich oder verschieden und stehen besonders bevorzugt für C1- C4-Alkyl oder R16 und R17 stehen zusammen besonders bevorzugt für einen C2-C3-Alkandιylrest, der gegebenenfalls durch C1-C4-Alkyl oder durch gegebenenfalls durch C1-
C2-Alkyl, C1-C2-Halogenalkyl, C1-C2-Alkoxy, C1-C2-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl substituiert ist. X steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso-Propyl, Butyl, iso-Butyl, tert.-Butyl, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano R 16 and R 17 are the same or different and are particularly preferably C 1 -C 4 -alkyl or R 16 and R 17 together are particularly preferably a C 2 -C 3 -alkanedyl radical which may be substituted by C 1 -C 4 - Alkyl or by optionally by C 1 - C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, nitro or cyano substituted phenyl. X very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoromethoxy, nitro or cyano
oder zwei Substituenten X bilden gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Methoxy, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano substituierten, ungesättigten 6-gliedrigen Carbocyclus. n steht ganz besonders bevorzugt für 1,2 oder 3. Z steht ganz besonders bevorzugt für eine der Gruppen or two substituents X together with the carbon atoms to which they are attached form an unsaturated 6-membered carbocycle optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano. n very particularly preferably represents 1, 2 or 3. Z very particularly preferably represents one of the groups
A steht ganz besonders bevorzugt für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl, C6-C4-Alkenyl, C1-C6- Alkoxy-C1-C4-alkyl, Poly-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-Alkylthio-C1- C4-alkyl, Cycloalkyl mit 3 bis 6 Ringatomen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso- Propyl, Methoxy, Ethoxy, Trifluormethyl oder Nitro substituiertes Phenyl, Furanyl, Pyridyl, Imidazolyl, Pyrazolyl, Triazolyl, Indolyl, Thiazolyl, Thienyl oder Benzyl. B steht ganz besonders bevorzugt für Wasserstoff, C1-C8-Alkyl oder C1-C4- Alkoxy-C1-C2-alkyl oder A very particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 8 -alkyl, C 6 -C 4 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, poly-C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 6 alkylthio-C 1 - C 4 alkyl, cycloalkyl having 3 to 6 ring atoms, in which a methylene group is optionally replaced by oxygen or sulfur, or for phenyl, furanyl, pyridyl, imidazolyl, pyrazolyl, triazolyl, indolyl, thiazolyl, thienyl or benzyl, each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or nitro. B very particularly preferably represents hydrogen, C 1 -C 8 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or
A, B und das Kohlenstoffatom an das sie gebunden sind, stehen ganz besonders bevorzugt für einen gesättigten oder ungesättigten C3-C8-Spirocyclus, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, und der gegebenenfalls einfach oder mehrfach durch Methyl, Ethyl,A, B and the carbon atom to which they are attached are very particularly preferably a saturated or unsaturated C 3 -C 8 spirocycle, in which a methylene group may have been replaced by oxygen or sulfur, and which may be mono- or polysubstituted by methyl, ethyl ,
Propyl, Isopropyl, Butyl, iso-Butyl, sec.-Butyl, tert,-Butyl, Cyclohexyl, Trifluormethyl, Methoxy, Ethoxy, Propoxy, iso-Propoxy, Butoxy, iso- Butoxy, sek.-Butoxy, tert.-Butoxy, Methylthio, Ethylthio, Fluor, Chlor oder Phenyl substituiert ist oder A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen ganz besonders bevorzugt für einen C3-C6-Spirocyclus, der durch eine gegebenenfalls durch ein Sauerstoff- oder Schwefelatom unterbrochene Alkylendiyl- oder durch eine Alkylendioxyl-Gruppe substituiert ist, die mit dem Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis siebengliedrigen Spirocyclus bildet oder Propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, propoxy, iso-propoxy, butoxy, iso-butoxy, sec-butoxy, tert-butoxy, Methylthio, ethylthio, fluorine, chlorine or phenyl is substituted or A, B and the carbon atom to which they are attached very particularly preferably represent a C 3 -C 6 spirocycle, which is interrupted by an optionally interrupted by an oxygen or sulfur atom Alkylenediyl- or substituted by an alkylenedioxyl group which forms a further five- to seven-membered spirocycle with the carbon atom to which it is attached or
A, B und das Kohlenstoffatom, an das sie gebunden sind, stehen ganz besonders bevorzugt für einen C3-C6-Spirocyclus, bei dem zwei Substituenten gemeinsam für einen gesättigten oder einfach bis dreifach ungesättigten fünf- oder sechsgliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoff- oder Schwefelatom enthält. A, B and the carbon atom to which they are attached very particularly preferably represent a C 3 -C 6 -spirocycle, in which two substituents together represent a saturated or mono- to tri-unsaturated five- or six-membered cycle, which may be one Contains oxygen or sulfur atom.
D steht ganz besonders bevorzugt für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl, C3-C4-Alkenyl, C3-C4-
Alkinyl, C1-C6-Alkoxy-C2-C4-alkyl, Poly-C1-C4-alkoxy-C2-C4-alkyl, C1-C4- Alkylthio-C2-C4-alkyl, C3-C6-Cycloalkyl, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, oder jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso- Propyl, Methoxy, Ethoxy, Trifluormethyl oder Nitro substituiertes Phenyl, Benzyl, Pyridyl, Thienyl, Furanyl oder Thiazolyl oder D very particularly preferably represents hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 8 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 - Alkynyl, C 1 -C 6 alkoxy-C 2 -C 4 alkyl, poly-C 1 -C 4 alkoxy-C 2 -C 4 alkyl, C 1 -C 4 - alkylthio-C 2 -C 4 - alkyl, C 3 -C 6 cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur, or in each case phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or nitro , Benzyl, pyridyl, thienyl, furanyl or thiazolyl or
A und D stehen ganz besonders bevorzugt gemeinsam mit den Atomen, an die sie gebunden sind für eine C3-C5-Alkandiyl- oder C3-C5-Alkendiylgruppierung, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist und welche gegebenenfalls durch Fluor, Chlor, Hydroxy, Mercapto oder durch jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C6-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C3-C6-Cycloalkyl, Phenyl oder Benzyloxy substituiert ist, oder, im Falle von Verbindungen der Formel (I-l), für eine der folgenden Gruppierungen A and D very particularly preferably together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by Fluorine, chlorine, hydroxy, mercapto or by C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 3 -C 6 cycloalkyl, phenyl or each optionally substituted by fluorine or chlorine Benzyloxy is substituted, or, in the case of compounds of the formula (II), for one of the following groupings
Q1, Q2, Q3 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl oder Ethyl oder Q 1 , Q 2 , Q 3 independently of one another very particularly preferably represent hydrogen, methyl or ethyl or
B und Q1 stehen gemeinsam ganz besonders bevorzugt für eine C1-C4-Alkandiylgruppierung, die gegebenenfalls durch Fluor, Chlor, Methyl oder Ethyl substituiert ist. G steht ganz besonders bevorzugt für Wasserstoff (a) oder für eine der Gruppen ,
in welchen B and Q 1 together very particularly preferably represent a C 1 -C 4 -alkanediyl group which is optionally substituted by fluorine, chlorine, methyl or ethyl. G very particularly preferably represents hydrogen (a) or one of the groups in which
E für ein Metallionäquivalent oder ein Ammoniumion steht, L für Sauerstoff oder Schwefel steht und
M für Sauerstoff oder Schwefel steht. 1 steht ganz besonders bevorzugt für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C14-AIkyl, C2-C14-Alkenyl, C1-C4-Alkoxy-C1-C6- alkyl, C1-C4-Alkylthio-C1-C6-alkyl, Poly-C1-C4-alkoxy-C1-C4-alkyl oder gegebenenfalls durch Fluor, Chlor, Methyl, Ethyl, Propyl, i-Propyl, Butyl, i-Butyl oder tert.-Butyl substituiertes C3-C6-Cycloalkyl, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, i- Propyl, Methoxy, Ethoxy, Trifluormethyl, Trifluormethoxy, Methylthio,E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M stands for oxygen or sulfur. 1 very particularly preferably represents in each case optionally substituted by fluorine or chlorine, C 1 -C 14 -alkyl, C 2 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 4 -Alkylthio-C 1 -C 6 alkyl, poly-C 1 -C 4 alkoxy-C 1 -C 4 alkyl or optionally by fluorine, chlorine, methyl, ethyl, propyl, i-propyl, butyl, i-butyl or tert-butyl substituted C 3 -C 6 cycloalkyl, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, for optionally by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl , Methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio,
Ethylthio, Methylsulfonyl, Ethylsulfonyl oder Nitro substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, i- Propyl, Methoxy, Ethoxy, Trifluormethyl oder Trifluormethoxy substituiertes Benzyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Furanyl, Thienyl, Pyridyl, Pyrimidyl, Thiazolyl oder Pyrazolyi, für gegebenenfalls durch Fluor, Chlor, Methyl oder Ethyl substituiertes Phenoxy-C1-C4-alkyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Amino, Methyl oder Ethyl substituiertes Pyridyloxy-C1 -C4-alkyl, Pyrimidyloxy-C1-C4-alkyl und Thiazolyloxy-C1-C4-alkyl Ethylthio, methylsulfonyl, ethylsulfonyl or nitro substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl substituted furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyi, for phenoxy-C 1 -C 4 -alkyl optionally substituted by fluorine, chlorine, methyl or ethyl, or for each optionally substituted by fluorine, chlorine, amino, methyl or ethyl substituted pyridyloxy-C 1 -C 4 alkyl, pyrimidyloxy-C 1 -C 4 alkyl and thiazolyloxy-C 1 -C 4 alkyl
R2 steht ganz besonders bevorzugt für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C14-Alkyl, C3-C14-Alkenyl, C1-C4-Alkoxy-C1-C6- alkyl oder Poly-C1-C4-alkoxy-C1-C6-alkyl, für gegebenenfalls durch Fluor, Chlor, Methyl, Ethyl, Propyl, iso-Propyl oder Methoxy substituiertes C3-C6-Cycloalkyl,
oder für jeweils gegebenenfalls durch Fluor, Chlor, Nitro, Methyl, Ethyl, Propyl, i-Propyl, Methoxy, Ethoxy oder Trifluormethyl substituiertes Phenyl oder Benzyl. R 2 very particularly preferably represents C 1 -C 14 -alkyl, C 3 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl or poly-C 1, each optionally substituted by fluorine or chlorine -C 4 -alkoxy-C 1 -C 6 -alkyl, for C 3 -C 6 -cycloalkyl optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl or methoxy, or for phenyl or benzyl optionally substituted by fluorine, chlorine, nitro, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy or trifluoromethyl.
R3 steht ganz besonders bevorzugt für gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl oder für jeweils gegebenenfalls durch Fluor,R 3 very particularly preferably represents C 1 -C 4 -alkyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine,
Chlor, Brom, Methyl, Methoxy, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl. Chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano substituted phenyl or benzyl.
R4 und R5 stehen ganz besonders bevorzugt unabhängig voneinander für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl, C1-C4- Alkoxy, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylthio oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, Cyano, C1-C2- Alkoxy, C1-C2-Fluoralkoxy, C1-C2-Alkylthio, C1-C2-Fluoralkylthio oder C1-C3-Alkyl substituiertes Phenyl, Phenoxy oder Phenylthio. R 4 and R 5 very particularly preferably independently of one another each represent C 1 -C 4 -alkyl which is optionally substituted by fluorine or chlorine, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C 1 -C 4 ) 4- alkyl) -amino, C 1 -C 4 -alkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2 -alkoxy, C 1 -C 2 -fluoroalkoxy, C 1 -C 2 Alkylthio, C 1 -C 2 fluoroalkylthio or C 1 -C 3 alkyl substituted phenyl, phenoxy or phenylthio.
R und R stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C3-C4-Alkenyl, C1- C4-Alkoxy-C1-C4-alkyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1- C4-Halogenalkyl, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxy substituiertes Benzyl, oder zusammen für C4-C6- Alkandiyl, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist. R and R independently of one another very particularly preferably represent hydrogen, in each case optionally substituted by fluorine, chlorine or bromine, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyl, C 1 - C 4 alkoxy-C 1 -C 4 -alkyl, optionally substituted by fluorine, chlorine, bromine, C 1 - C 4 haloalkyl, C 1 -C 4 alkyl or C 1 -C 4 -Alkoxy substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy, or together for C 4 -C 6 alkane diyl , in which a methylene group is optionally replaced by oxygen or sulfur.
Für n >1 können die Reste X gleich oder verschieden sein. For n> 1, the radicals X can be the same or different.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können untereinander, also auch zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend. The general definitions or explanations of residues or explanations listed above or in preferred areas can be combined with one another, that is to say also between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.
Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt (vorzugsweise) aufgeführten Bedeutungen vorliegt.
Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred). According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Gesättigte oder ungesättigte Kohlenwasserstoffreste können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein. Verwendet man gemäß Verfahren (A) N-[3-(2-Chlor)-thienylacetyl]-1-amino-4- ethyl-cyclohexan-carbonsäureethylester als Ausgangsstoff, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden: Saturated or unsaturated hydrocarbon residues, also in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched. If, according to process (A), N- [3- (2-chloro) -thienylacetyl] -1-amino-4-ethyl-cyclohexane-carboxylic acid ethyl ester is used as the starting material, the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (B) O-[2-(3-Methyl)-thienylacetyI]-hydroxyessigsäureethylester, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden: If O- [2- (3-methyl) -thienylacetyI] -hydroxyacetic acid ethyl ester is used according to process (B), the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (C) 2-[2-(3,5-Dichlor)-tienyl]-4-(4-methoxy)- benzylmercapto-4-methyl-3-oxo-valeriansäure-ethylester, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden:
If 2- (2- (3,5-dichloro) tienyl] -4- (4-methoxy) benzylmercapto-4-methyl-3-oxo-valeric acid ethyl ester is used according to process (C), the course of the The process according to the invention can be represented by the following reaction scheme:
Verwendet man beispielsweise gemäß Verfahren (D-α) (Chlorcarbonyl)-3-(2-methyl)-thienylketen und 1,2-Diazacyclopentan als Ausgangsverbindungen, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden: If, for example, according to process (D-α) (chlorocarbonyl) -3- (2-methyl) -thienyl ketene and 1,2-diazacyclopentane are used as starting compounds, the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man beispielsweise gemäß Verfahren (D-ß) 3-(2,4-Dimethyl-thienylmalonsäurediethylester und 1,2-Diazacyclopentan als Ausgangsverbindungen, so kann der Verlauf des erfindungsgemäßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werden: If, for example, 3- (2,4-dimethyl-thienylmalonic acid diethyl ester and 1,2-diazacyclopentane are used as starting compounds according to process (D-β), the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man beispielsweise gemäß Verfahren (E) (Chlorcarbonyl)-2-(3-methyl)- thienylketen und Aceton als Ausgangsverbindung, so kann der Verlauf des erfindungsgemäßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werden:
If, for example, according to process (E) (chlorocarbonyl) -2- (3-methyl) thienyl ketene and acetone are used as the starting compound, the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man beispielsweise gemäß Verfahren (F) (Chlorcarbonyl)-2-(3-chlor)-thienylketen und Thiobenzamid als Ausgangsverbindungen, so kann der Verlauf des erfindungsgemäßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werden: If, for example, according to process (F) (chlorocarbonyl) -2- (3-chloro) thienyl ketene and thiobenzamide are used as starting compounds, the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (G) 5-[2-(3-Methyl-5-chlor)-thienyl)-2,2-dimethyl-4-oxo-valeriansäure-ethylester, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden. If, according to process (G), 5- [2- (3-methyl-5-chloro) thienyl) -2,2-dimethyl-4-oxo-valeric acid ethyl ester is used, the course of the process according to the invention can be represented by the following reaction scheme become.
Verwendet man gemäß Verfahren (H) 6-[3-(2,5-Dichlor)-thienyl]-5-oxo-capronsäureethylester, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden:
If 6- [3- (2,5-dichloro) thienyl] -5-oxo-caproic acid ethyl ester is used according to process (H), the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (Iα) 3-[2-(3-Methyl)thienyl)]-5,5-dimethylpyrrolidin-2,4-dion und Pivaloylchlorid als Ausgangsstoffe, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden: If, according to process (I α ), 3- [2- (3-methyl) thienyl)] - 5,5-dimethylpyrrolidine-2,4-dione and pivaloyl chloride are used as starting materials, the course of the process according to the invention can be represented by the following reaction scheme :
Verwendet man gemäß Verfahren (I) (Variante ß) 3-[3-(2,5-Dichlor)-thienyl]-4-hydroxy-5-phenyl-Δ3-dihydrofuran-2-on und Acetanhydrid als Ausgangsverbindungen, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden: If, according to process (I) (variant β), 3- [3- (2,5-dichloro) -thienyl] -4-hydroxy-5-phenyl-Δ 3 -dihydrofuran-2-one and acetic anhydride are used as starting compounds, then the course of the process according to the invention can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (J) 8-[2-(3-Chlor)-thienyl]-1,6-diaza-bicyclo- (4,3,01 ,6)-nonan-7,9-dion und Chlorameisensäureethoxyethylester als Ausgangsverbindungen, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden.
According to process (J), 8- [2- (3-chloro) thienyl] -1,6-diaza-bicyclo- (4,3,0 1, 6 ) -nonane-7,9-dione and chloroformic acid ethoxyethyl ester are used as Starting compounds, the course of the process according to the invention can be represented by the following reaction scheme.
Verwendet man gemäß Verfahren (K, Variante α) 3-[3-(2,4,5-Trimethyl)-thienyl]-4-hydroxy-6-(3-pyridyl)-pyron und Chlormonothioameisensäuremethylester als Ausgangsprodukte, so kann der Reaktionsverlauf folgendermaßen wiedergegeben werden: If, according to process (K, variant α), 3- [3- (2,4,5-trimethyl) -thienyl] -4-hydroxy-6- (3-pyridyl) -pyrone and methyl chloromothio formate are used as starting products, the course of the reaction can are reproduced as follows:
Verwendet man gemäß Verfahren (K, Variante ß) 5-[2-(3,4-Dimethyl)-thienyl]-6- hydroxy-2-(4-chlorphenyl)-thiazin-4-on, Schwefelkohlenstoff und Methyliodid als Ausgangskomponenten, so kann der Reaktionsverlauf wie folgt wiedergegeben werden: If, according to process (K, variant β), 5- [2- (3,4-dimethyl) thienyl] -6-hydroxy-2- (4-chlorophenyl) thiazin-4-one, carbon disulfide and methyl iodide are used as starting components, the reaction process can be represented as follows:
Verwendet man gemäß Verfahren (L) 2-[3-(2-Methyl)-thienyl-3-hydroxy-4,4-(3- methoxy)-pentamethylen-Δ2-cyclopentenon und Methansulfonsäurechlorid als Ausgangsprodukt, so kann der Reaktionsverlauf durch folgendes Reaktionsschema wiedergegeben werden:
If 2- (3- (2-methyl) -thienyl-3-hydroxy-4,4- (3-methoxy) -pentamethylene-Δ 2 -cyclopentenone and methanesulfonic acid chloride) is used as the starting product in process (L), the course of the reaction can be followed by the following reaction scheme can be reproduced:
Verwendet man gemäß Verfahren (M) 2-[3-(2-Chlor)-thienyl]-3-hydroxy-4,4-dimethyl-Δ2-cyclohexenon und Methanthio-phosphonsäurechlorid-(2,2,2-trifluorethylester) als Ausgangsprodukte, so kann der Reaktionsverlauf durch folgendes Reaktionsschema wiedergegeben werden: According to method (M) 2- [3- (2-chloro) thienyl] -3-hydroxy-4,4-dimethyl-Δ 2 -cyclohexenone and methanthophosphonyl chloride (2,2,2-trifluoroethyl ester) are used as Starting products, the course of the reaction can be represented by the following reaction scheme:
Verwendet man gemäß Verfahren (N) 3-[2-(3,4-Dimethyl)-thienyl]-5-cyclopropyl- 5-methyl-pyrrolidin-2,4-dion und NaOH als Komponenten, so kann der Verlauf des erfindungsgemäßen Verfahrens durch folgendes Reaktionsschema wiedergegeben werden If, according to process (N), 3- [2- (3,4-dimethyl) thienyl] -5-cyclopropyl-5-methyl-pyrrolidine-2,4-dione and NaOH are used as components, the course of the process according to the invention can are represented by the following reaction scheme
Na(+)
Well (+)
Verwendet man gemäß Verfahren (O, Variante α) 3-[2-(3,4,5-Trichlor)-thienyl]-4- hydroxy-5-tetramethylen-Δ3-dihydro-furan-2-on und Ethylisocyanat als Ausgangsprodukte, so kann der Reaktionsverlauf durch folgendes Reaktionsschema wiedergegeben werden
According to process (O, variant α), 3- [2- (3,4,5-trichloro) thienyl] -4-hydroxy-5-tetramethylene-Δ 3 -dihydro-furan-2-one and ethyl isocyanate are used as starting products , the course of the reaction can be represented by the following reaction scheme
Verwendet man gemäß Verfahren (O; Variante ß) 3-[3-(2-Methyl)-thienyl]-5-methyl-pyrrolidin-2,4-dion und Dimethylcarbamidsäurechlorid als Ausgangsprodukte, so kann der Reaktionsverlauf durch folgendes Schema wiedergegeben werden: If 3- [3- (2-methyl) -thienyl] -5-methyl-pyrrolidin-2,4-dione and dimethylcarbamoyl chloride are used as starting products according to process (O; variant β), the course of the reaction can be represented by the following scheme:
Die beim erfindungsgemäßen Verfahren (A) als Ausgangsstoffe benötigten Verbindungen der Formel (II) The compounds of the formula (II) required as starting materials in process (A) according to the invention
in welcher in which
A, B, D, X, n und R8 die oben angegebenen Bedeutungen haben, sind neu A, B, D, X, n and R 8 have the meanings given above are new
Man erhält die Verbindungen der Formel (II) beispielsweise, wenn man Aminosaurederivate der Formel (XXIII)
The compounds of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XXIII)
in welcher in which
A, B, R8 und D die oben angegebenen Bedeutungen haben, mit Thienylessigsäurehalogeniden der Formel (XXIV)
in welcher A, B, R 8 and D have the meanings given above, with thienylacetic acid halides of the formula (XXIV) in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Chlor oder Brom steht, acyliert (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968) oder wenn man Acylaminosäuren der Formel (XXV) Hal represents chlorine or bromine, acylated (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968) or if acylamino acids of the formula (XXV)
in welcher in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, verestert (Chem. Ind. (London) 1568 (1968)). A, B, D, X and n have the meanings given above, esterified (Chem. Ind. (London) 1568 (1968)).
Die Verbindungen der Formel (XXV)
in welcher The compounds of formula (XXV) in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, sind neu. Man erhält die Verbindungen der Formel (XXV), wenn man Aminosäuren derA, B, D, X and n have the meanings given above are new. The compounds of formula (XXV) are obtained when amino acids of
Formel (XXVI) Formula (XXVI)
in welcher in which
A, B und D die oben angegebenen Bedeutungen haben, mit Thienylessigsäurehalogeniden der Formel (XXIV)
in welcher A, B and D have the meanings given above, with thienylacetic acid halides of the formula (XXIV) in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Chlor oder Brom steht, nach Schotten-Baumann acyliert (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, S. 505) Hal stands for chlorine or bromine, acylated according to Schotten-Baumann (Organikum, VEB German Publishing House of Sciences, Berlin 1977, p. 505)
Die Verbindungen der Formel (XXIV) sind teilweise bekannt oder lassen sich nach bekannten Verfahren darstellen.
Die Verbindungen der Formel (XXIII) und (XXVI) sind teilweise bekannt und/oder lassen sich nach bekannten Verfahren darstellen Some of the compounds of the formula (XXIV) are known or can be prepared by known processes. Some of the compounds of the formulas (XXIII) and (XXVI) are known and / or they can be prepared by known processes
Die substituierten cyclischen Aminocarbonsäuren der Formel (XXVIa), in der A und B einen Ring bilden, sind im allgemeinen nach der Bucherer-Bergs-Synthese oder nach der Strecker-Synthese erhältlich und fallen dabei jeweils in unterschiedlichen Isomerenformen an. So erhält man nach den Bedingungen der Bucherer-Bergs-Synthese vorwiegend die Isomeren (im folgenden der Einfachheit halber als ß bezeichnet), in welchen die Reste R und die Carboxylgruppe äquatorial stehen, während nach den Bedingungen der Strecker- Synthese vorwiegend die Isomeren (im folgenden der Einfachheit halber als α bezeichnet) anfallen, bei denen die Aminogruppe und die Reste R äquatorial stehen The substituted cyclic aminocarboxylic acids of the formula (XXVIa), in which A and B form a ring, are generally obtainable after the Bucherer-Bergs synthesis or after the Strecker synthesis and are each obtained in different isomer forms. Thus, according to the conditions of the Bucherer-Bergs synthesis, predominantly the isomers (hereinafter referred to as β for the sake of simplicity), in which the radicals R and the carboxyl group are in equatorial fashion, are obtained, while the isomers (im following for the sake of simplicity referred to as α) in which the amino group and the radicals R are equatorial
Bucherer-Bergs-Synthese Strecker-Synthese Bucherer-Bergs synthesis Strecker synthesis
(ß-Isomeres) (α-Isomeres) (L Munday, J Chem Soc 4372 (1961); J.T Eward, C Jitrangeri, Can J Chem (β-isomer) (α-isomer) (L Munday, J Chem Soc 4372 (1961); J.T Eward, C Jitrangeri, Can J Chem
53, 3339 (1975) 53, 3339 (1975)
Weiterhin lassen sich die bei dem obigen Verfahren (A) verwendeten Ausgangsstoffe der Formel (II) The starting materials of the formula (II) used in process (A) above can also be
in welcher in which
A, B, D, X, n und R8 die oben angegebenen Bedeutungen haben,
herstellen, wenn man Aminonitrile der Formel (XXVII)
A, B, D, X, n and R 8 have the meanings given above, produce if aminonitriles of the formula (XXVII)
in welcher in which
A, B und D die oben angegebenen Bedeutungen haben, mit Thienylessigsäurehalogeniden der Formel (XXIV)
A, B and D have the meanings given above, with thienylacetic acid halides of the formula (XXIV)
in welcher in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Chlor oder Brom steht, Hal represents chlorine or bromine,
zu Verbindungen der Formel (XVIII)
to compounds of the formula (XVIII)
in welcher in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, umsetzt, A, B, D, X and n have the meanings given above,
und diese anschließend einer sauren Alkoholyse unterwirft
Die Verbindungen der Formel (XXVIII) sind ebenfalls neu and then subjecting it to acidic alcoholysis The compounds of formula (XXVIII) are also new
Die bei dem erfindungsgemäßen Verfahren (B) als Ausgangstoffe benotigten Verbindungen der Formel (III) The compounds of the formula (III) required as starting materials in process (B) according to the invention
in welcher in which
A, B, X, n und R8 die oben angegebenen Bedeutungen haben, sind neu A, B, X, n and R 8 have the meanings given above are new
Sie lassen sich nach im Prinzip bekannten Methoden in einfacher Weise herstellen They can be produced in a simple manner using methods which are known in principle
So erhalt man die Verbindungen der Formel (III) beispielsweise, wenn man 2-Hydroxycarbonsaureester der Formel (XXIX)
in welcher For example, the compounds of the formula (III) are obtained when 2-hydroxycarboxylic acid esters of the formula (XXIX) in which
A, B und R8 die oben angegebenen Bedeutungen haben, mit Thienylessigsäurehalogeniden der Formel (XXIV)
in welcher
X und n die oben angegebenen Bedeutungen haben und A, B and R 8 have the meanings given above, with thienylacetic acid halides of the formula (XXIV) in which X and n have the meanings given above and
Hal für Chlor oder Brom steht. acyliert (Chem. Reviews 52, 237-416 (1953)). Hal stands for chlorine or bromine. acylated (Chem. Reviews 52, 237-416 (1953)).
Weiterhin erhält man Verbindungen der Formel (III), wenn man Furthermore, compounds of the formula (III) are obtained if
Thienylessigsäuren der Formel (XXX)
in welcher Thienylacetic acids of the formula (XXX) in which
X und n die oben angegebenen Bedeutungen haben, mit α-Halogencarbonsäureestern der Formel (XXXI) X and n have the meanings given above, with α-halocarboxylic acid esters of the formula (XXXI)
in welcher in which
A, B und R8 die oben angegebenen Bedeutungen haben und A, B and R 8 have the meanings given above and
Hal für Chlor oder Brom steht, alkyliert. Die Verbindungen der Formeln (XXX) und (XXXI) sind allgemein bekannte Verbindungen und/oder lassen sich nach bekannten Verfahren in einfacher Weise herstellen
Die bei dem obigen Verfahren (C) als Ausgangsstoffe benötigten Verbindungen der Formel (IV) Hal represents chlorine or bromine, alkylated. The compounds of the formulas (XXX) and (XXXI) are generally known compounds and / or can be prepared in a simple manner by known processes The compounds of the formula (IV) required as starting materials in process (C) above
in welcher in which
A, B, W, X, n und R8 die oben angegebenen Bedeutungen haben, sind neu. A, B, W, X, n and R 8 have the meanings given above are new.
Sie lassen sich nach im Prinzip bekannten Methoden herstellen. They can be produced using methods that are known in principle.
Man erhält die Verbindungen der Formel (IV), wenn man The compounds of formula (IV) are obtained when
Thienylessigsäureester der Formel (XXXII)
Thienylacetic acid esters of the formula (XXXII)
in welcher in which
X, R8 und n die oben angegebenen Bedeutungen haben, X, R 8 and n have the meanings given above,
mit 2-Benzylthio-carbonsäurehalogeniden der Formel (XXXIII)
in welcher with 2-benzylthio-carboxylic acid halides of the formula (XXXIII) in which
A, B und W die oben angegebenen Bedeutungen haben und A, B and W have the meanings given above and
Hal für Halogen, insbesondere Chlor oder Brom steht, in Gegenwart von starken Basen acyliert (siehe z.B. M S. Chambers, E.J. Thomas, DJ. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228). Hal stands for halogen, especially chlorine or bromine, acylated in the presence of strong bases (see e.g. M S. Chambers, E. J. Thomas, DJ. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228).
Die Verbindungen der Formel (XXXII) sind literaturbekannt, leicht verfügbar und teilweise käufliche Verbindungen. The compounds of the formula (XXXII) are known from the literature, are readily available and some are commercially available compounds.
Die Benzylthio-carbonsäurehalogenide der Formel (XXXIII) sind teilweise bekannt und/oder lassen sich nach bekannten Verfahren herstellen (J. Antibiotics (1983), 26, 1589). Some of the benzylthio-carboxylic acid halides of the formula (XXXIII) are known and / or can be prepared by known processes (J. Antibiotics (1983), 26, 1589).
Die bei dem obigen Verfahren (Da) als Ausgangsstoffe benötigten Halogencarbonylketene der Formel (V) sind neu. Sie lassen sich nach im Prinzip bekannten Methoden in einfacher Weise herstellen (vgl. beispielsweise Org. Prep. Proced. Int., 7, (4), 155-158, 1975 und DE 1 945 703). So erhält man die Verbindungen der Formel (V) The halocarbonyl ketene of the formula (V) required as starting materials in the above process (Da) are new. They can be produced in a simple manner by methods known in principle (cf. for example Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE 1 945 703). This gives the compounds of the formula (V)
in welcher in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Chlor oder Brom steht, wenn man Hal stands for chlorine or bromine if one
Thienylmalonsäuren der Formel (XXXIV)
in welcher Thienylmalonic acids of the formula (XXXIV) in which
X und n die oben angegebenen Bedeutungen haben, mit Säurehalogeniden, wie beispielsweise Thionylchlorid, Phosphor(V)chlorid, Phosphor(III)chlorid, Oxalylchlorid, Phosgen oder Thionylbromid gegebenenfalls in Gegenwart von Katalysatoren, wie beispielsweise Diethylformamid, Methyl-Sterylformamid oder Triphenylphosphin und gegebenenfalls in Gegenwart von Basen wie z.B. Pyridin oderTriethylamin, umsetzt. X and n have the meanings given above, with acid halides, such as, for example, thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate in the presence of catalysts, such as, for example, diethylformamide, methyl sterylformamide or triphenylphosphine and if appropriate in the presence of bases such as Pyridine or triethylamine.
Die Thienylmalonsäuren der Formel (XXXIV) sind teilweise bekannte Verbindungen der organischen Chemie und lassen sich in einfacher Weise nach bekanntenSome of the thienylmalonic acids of the formula (XXXIV) are known compounds of organic chemistry and can easily be prepared according to known ones
Verfahren herstellen (vgl. z.B. Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, S. 517 ff). Produce processes (see e.g. Organikum, VEB German Publishing House of Sciences, Berlin 1977, p. 517 ff).
Die bei dem obigen Verfahren (D ß) als Ausgangsstoffe benötigten Malonsäureester der Formel (VI) The malonic esters of the formula (VI) required as starting materials in the above process (D ß)
in welcher in which
R8, X und n die oben angegebenen Bedeutungen haben, sind teilweise bekannt und lassen sich nach allgemein bekannten Methoden der organischen Chemie darstellen (vgl. z.B. Tetrahedron Lett. 27, 2763 (1986) und Organikum VEB Deutscher Verlag der Wissenschaften, Berlin 1977, S. 587 ff). R 8 , X and n have the meanings given above, are known in some cases and can be prepared by generally known methods of organic chemistry (cf., for example, Tetrahedron Lett. 27, 2763 (1986) and Organikum VEB German Publishing House of Sciences, Berlin 1977, P. 587 ff).
Die zur Durchführung der erfindungsgemäßen (D-α) und (D-ß) außerdem als Ausgangsstoffe benötigten Hydrazine der Formel (VII) The hydrazines of the formula (VII) which are also required as starting materials for carrying out the (D-α) and (D-β) according to the invention
A-NH-NH-D (VII),
in welcher A-NH-NH-D (VII), in which
A und D die oben angegebenen Bedeutungen haben, sind teilweise bekannt und/oder nach literaturbekannten Methoden herstellbar (vgl. beispielsweise Liebigs Ann. Chem. 585. 6 (1954); Reaktionen der organischen Synthese, C. Ferri, Seite 212, 513; Georg Thieme Verlag Stuttgart, 1978; LiebigsA and D have the meanings given above, are known in some cases and / or can be prepared by methods known from the literature (cf. for example Liebigs Ann. Chem. 585.6 (1954); Reactions of Organic Synthesis, C. Ferri, pages 212, 513; Georg Thieme Verlag Stuttgart, 1978; Liebigs
Ann. Chem. 443, 242 (1925); Chem. Ber. 98, 2551 (1965), EP 508 126). Ann. Chem. 443, 242 (1925); Chem. Ber. 98, 2551 (1965), EP 508 126).
Die Herstellung der zur Durchführung des erfindungsgemäßen Verfahrens (E) als Ausgangsstoffe benötigten Ketensäurehalogenide der Formel (V) wurden bereits beim erfindungsgemäßen Verfahren (D) beschrieben. Die für das erfindungsgemäße Verfahren (E) als Ausgangsstoffe benötigten Carbonylverbindungen der Formel (VIII) The preparation of the ketonic acid halides of the formula (V) required as starting materials for carrying out process (E) according to the invention has already been described in process (D) according to the invention. The carbonyl compounds of the formula (VIII) required as starting materials for process (E) according to the invention
in welcher in which
A und D die oben angegebenen Bedeutungen haben, sind käufliche, allgemeine bekannte oder nach bekannten Verfahren zugänglicheA and D have the meanings given above, are commercially available, generally known or accessible by known processes
Verbindungen. Links.
Die Herstellung der zur Durchführung des erfindungsgemäßen Verfahrens (F) als Ausgangsstoffe benötigten Ketensäurechloride der Formel (V) wurden bereits beim erfindungsgemäßen Verfahren (D) beschrieben. Die zur Durchführung des erfindungsgemäßen Verfahrens (F) benötigten Thioamide der Formel (IX)
in welcher The preparation of the ketene acid chlorides of the formula (V) required as starting materials for carrying out process (F) according to the invention has already been described in process (D) according to the invention. The thioamides of the formula (IX) required for carrying out process (F) according to the invention in which
A die oben angegebene Bedeutung hat,
sind allgemein in der organischen Chemie bekannte Verbindungen. A has the meaning given above, are generally known compounds in organic chemistry.
Die bei dem obigen Verfahren (G) als Ausgangsstoffe benötigten Verbindungen der Formel (X) The compounds of the formula (X) required as starting materials in process (G) above
in welcher in which
A, B, D, Q1, X, n und R8 die oben angegebenen Bedeutungen haben, sind neu. Sie lassen sich nach im Prinzip bekannten Methoden herstellen. Man erhält die Verbindungen der Formel (X), wenn man 5-Thienyl-4-ketocarbonsäuren der Formel (XXXV) A, B, D, Q 1 , X, n and R 8 have the meanings given above are new. They can be produced using methods that are known in principle. The compounds of the formula (X) are obtained if 5-thienyl-4-ketocarboxylic acids of the formula (XXXV)
in welcher in which
X, A, B, D, Q1 und n die oben angegebenen Bedeutungen haben, verestert (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 499). X, A, B, D, Q 1 and n have the meanings given above, esterified (see, for example, Organikum, 15th edition, Berlin, 1977, page 499).
Die 5-Thienyl-4-ketocarbonsäuren der Formel (XXXV) The 5-thienyl-4-ketocarboxylic acids of the formula (XXXV)
in welcher
A, B, D, Q1, X und n die oben angegebenen Bedeutungen haben sind neu, lassen sich aber nach im Prinzip bekannten Methoden herstellen. in which A, B, D, Q 1 , X and n have the meanings given above are new, but can be prepared by methods known in principle.
Man erhält die Verbindungen der Formel (XXXV) beispielsweise, wenn man Carbonsäureanhydride der Formel (XXXVI) The compounds of the formula (XXXV) are obtained, for example, if carboxylic anhydrides of the formula (XXXVI)
in welcher in which
A, B, D und Q1 die oben angegebenen Bedeutungen haben, mit metall organischen Verbindungen der Formel (XXXVII)
in welcher A, B, D and Q 1 have the meanings given above, with organometallic compounds of the formula (XXXVII) in which
X und n die oben angegebenen Bedeutungen haben, X and n have the meanings given above,
Me für ein- oder zweiwertige Metallionen, wie beispielsweise Lithium oder Magnesium, Me for mono- or divalent metal ions, such as lithium or magnesium,
Hal für Chlor oder Brom und Hal for chlorine or bromine and
1 für 0 oder 1 steht, in Gegenwart eines Verdünnungsmittels (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 623) umsetzt.
Die Verbindungen (XXXVI) und (XXXVII) sind teilweise bekannt und/oder lassen sich nach bekannten Verfahren in einfacher Weise darstellen (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seiten 525, 526 und 623). 1 stands for 0 or 1, in the presence of a diluent (see, for example, Organikum, 15th edition, Berlin, 1977, page 623). Some of the compounds (XXXVI) and (XXXVII) are known and / or can be prepared in a simple manner by known processes (see, for example, Organikum, 15th edition, Berlin, 1977, pages 525, 526 and 623).
Weiterhin erhält man 5-Thienyl-4-ketocarbonsäuren der Formel (XXXV) 5-Thienyl-4-ketocarboxylic acids of the formula (XXXV)
in welcher in which
A, B, D, Q1, X und n die oben angegebenen Bedeutungen haben, wenn man 2-Thienyl-3-oxo-adipinsäureester der Formel (XXXVIII) A, B, D, Q 1 , X and n have the meanings given above if 2-thienyl-3-oxo-adipic acid esters of the formula (XXXVIII)
in welcher in which
A, B, D, Q1, X und n die oben angegebenen Bedeutungen haben und A, B, D, Q 1 , X and n have the meanings given above and
R8 und R8 gleich oder verschieden sind und für Alkyl, bevorzugt C1-C6-Alkyl stehen, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base oder Säure verseift und decarboxyliert (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 519 bis 521). R 8 and R 8 are the same or different and represent alkyl, preferably C 1 -C 6 alkyl, optionally saponified and decarboxylated in the presence of a diluent and optionally in the presence of a base or acid (see, for example, Organikum, 15th edition, Berlin , 1977, pages 519 to 521).
Die Verbindungen der Formel (XXXVIII)
in welcher The compounds of the formula (XXXVIII) in which
A, B, D, Q , X, R8, R8' und n die oben angegebenen Bedeutungen haben, sind erhältlich, wenn man Dicarbonsäurehalbesterchloride der Formel (XXXIX), A, B, D, Q, X, R 8 , R 8 ' and n have the meanings given above are available if dicarboxylic acid half-ester chlorides of the formula (XXXIX),
in welcher in which
A, B, D, Q1 und R8 die oben angegebenen Bedeutungen haben und Hal für Chlor oder Brom steht, mit Thienylessigsäureester der Formel (XXXII)
in welcher R8', X und n die oben angegebenen Bedeutungen haben, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base acyliert (vgl. z.B. M S. Chambers, E. J. Thomas, D.J. Williams, J. Chem. Soc. Chem. Commun, (1987), 1228). Die Verbindungen der Formeln (XXXII) und (XXXIX) sind allgemein bekannteA, B, D, Q 1 and R 8 have the meanings given above and Hal represents chlorine or bromine, with thienylacetic acid ester of the formula (XXXII) in which R 8 ' , X and n have the meanings given above, acylated in the presence of a diluent and in the presence of a base (see, for example, M S. Chambers, EJ Thomas, DJ Williams, J. Chem. Soc. Chem. Commun, (1987), 1228). The compounds of the formulas (XXXII) and (XXXIX) are generally known
Verbindungen der organischen Chemie und/oder lassen sich nach im Prinzip bekannten Methoden in einfacher Weise herstellen. Compounds of organic chemistry and / or can be prepared in a simple manner by methods known in principle.
Die bei dem obigen Verfahren (H) als Ausgangsstoffe benötigten Verbindungen der Formel (XI)
in welcher The compounds of the formula (XI) required as starting materials in process (H) above in which
A, B, D, Q1, Q2, Q3, X, n und R8 die oben angegebene Bedeutung haben, sind neu. Sie lassen sich nach im Prinzip bekannten Methoden herstellen. Man erhält die Verbindungen der Formel (XI), wenn man 6-Thienyl-5-ketocarbonsäuren der Formel (XL) A, B, D, Q 1 , Q 2 , Q 3 , X, n and R 8 have the meaning given above are new. They can be produced using methods that are known in principle. The compounds of the formula (XI) are obtained if 6-thienyl-5-ketocarboxylic acids of the formula (XL)
in welcher in which
X, A, B, D, Q1, Q2, Q3 und n die oben angegebenen Bedeutungen haben, verestert, (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 499). X, A, B, D, Q 1 , Q 2 , Q 3 and n have the meanings given above, esterified, (see, for example, Organikum, 15th edition, Berlin, 1977, page 499).
Die 6-Thienyl-5-ketocarbonsäuren der Formel (XL) The 6-thienyl-5-ketocarboxylic acids of the formula (XL)
in welcher in which
A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben sind neu, lassen sich aber nach im Prinzip bekannten Methoden herstellen.
Man erhält die Verbindungen der Formel (XL), wenn man Carbonsäureanhydride der Formel (XLI) A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above are new, but can be prepared by methods known in principle. The compounds of the formula (XL) are obtained if carboxylic anhydrides of the formula (XLI)
in welcher A, B, D, Q1, Q2 und Q3 die oben angegebenen Bedeutungen haben mit metall organischen Verbindungen der Formel (XXXVII)
in welcher in which A, B, D, Q 1 , Q 2 and Q 3 have the meanings given above with organometallic compounds of the formula (XXXVII) in which
X und n die oben angegebenen Bedeutungen haben, Me für ein- oder zweiwertige Metallionen, wie beispielsweise Lithium undX and n have the meanings given above, Me for mono- or divalent metal ions, such as lithium and
Magnesium, Magnesium,
Hal für Chlor oder Brom und Hal for chlorine or bromine and
1 für eine Zahl 0 oder 1 steht, in Gegenwart eines Verdünnungsmittels umsetzt (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 623).
Die Verbindungen (XXXVII) und (XLI) sind teilweise bekannt und/oder lassen sich nach bekannten Verfahren in einfacher Weise darstellen (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seiten 525, 526 und 623). 1 stands for a number 0 or 1, in the presence of a diluent (see, for example, Organikum, 15th edition, Berlin, 1977, page 623). Some of the compounds (XXXVII) and (XLI) are known and / or can be prepared in a simple manner by known processes (cf., for example, Organikum, 15th edition, Berlin, 1977, pages 525, 526 and 623).
Weiterhin erhält man 6-Thienyl-5-ketocarbonsäuren der Formel (XL) 6-Thienyl-5-ketocarboxylic acids of the formula (XL) are also obtained.
in welcher in which
A, B, D, Q1, Q2, Q3, X und n die oben angegebenen Bedeutungen haben, wenn man 2-Thienyl-3-oxo-heptandisäureester der Formel (XLII) A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given above if 2-thienyl-3-oxo-heptanedioate of the formula (XLII)
in welcher in which
A, B, D, Q1, Q2, Q3, X, R8, R8' und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base oder Säure verseift und decarboxyliert (vgl. z.B. Organikum, 15. Auflage, Berlin, 1977, Seite 519 bis 521). Die Verbindungen der Formel (XLII) A, B, D, Q 1 , Q 2 , Q 3 , X, R 8 , R 8 ' and n have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base or acid and saponified and decarboxylated (cf. e.g. Organikum, 15th edition, Berlin, 1977, pages 519 to 521). The compounds of the formula (XLII)
in welcher in which
A, B, D, Q1, Q2, Q3 Z, R8, R8' und n die oben angegebenen Bedeutungen haben, sind neu und erhältlich, wenn man Dicarbonsäurehalbesterchloride der Formel (XLIII), A, B, D, Q 1 , Q 2 , Q 3 Z, R 8 , R 8 ' and n have the meanings given above are new and obtainable if dicarboxylic acid half-ester chlorides of the formula (XLIII),
in welcher in which
A, B, D, Q1, Q2, Q3 und R8 die oben angegebenen Bedeutungen haben und A, B, D, Q 1 , Q 2 , Q 3 and R 8 have the meanings given above and
Hal für Chlor oder Brom steht, mit Thienylessigsäureestern der Formel (XXXII)
in welcher Hal represents chlorine or bromine, with thienylacetic acid esters of the formula (XXXII) in which
X, R8' und n die oben angegebenen Bedeutungen haben, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base acyliert (vgl. z.B. M.S. Chambers, E. J. Thomas, D J Williams, J Chem Soc Chem Commun, (1987), 1228) X, R 8 ' and n have the meanings given above, acylated in the presence of a diluent and in the presence of a base (see, for example, MS Chambers, EJ Thomas, DJ Williams, J Chem Soc Chem Commun, (1987), 1228)
Die Verbindungen der Formeln (XXXII) und (XLIII) sind allgemein bekannte Verbindungen der organischen Chemie und/oder lassen sich nach im Prinzip bekannten Methoden in einfacher Weise herstellen (vgl z B EP-A-0 307 103)
Die zur Durchführung der erfindungsgemäßen Verfahren (I), (J), (K), (L), (M), (N) und (O) außerdem als Ausgangsstoffe benötigten Säurehalogenide der Formel (XII), Carbonsäureanhydride der Formel (XIII), Chlorameisensäureester oder Chlorameisensäurethioester der Formel (XIV), Chlormonothioameisensäureester oder Chlordithioameisensäureester der Formel (XV), Alkylhalogenide der FormelThe compounds of the formulas (XXXII) and (XLIII) are generally known compounds of organic chemistry and / or can be prepared in a simple manner by methods known in principle (cf. for example EP-A-0 307 103) The acid halides of the formula (XII), carboxylic anhydrides of the formula (XIII) which are also required as starting materials for carrying out the processes (I), (J), (K), (L), (M), (N) and (O) , Chloroformic acid ester or chloroformic acid thioester of the formula (XIV), chloromothio formic acid ester or chlorodithio formic acid ester of the formula (XV), alkyl halides of the formula
(XVI), Sulfonsäurechloride der Formel (XVII), Phosphorverbindungen der Formel (XVIII) und Metallhydroxide, Metallalkoxide oder Amine der Formel (XIX) und (XX) und Isocyanate der Formel (XXI) und Carbamidsäurechloride der Formel (XXII) sind allgemein bekannte Verbindungen der organischen bzw. anorganischen Chemie. (XVI), sulfonic acid chlorides of the formula (XVII), phosphorus compounds of the formula (XVIII) and metal hydroxides, metal alkoxides or amines of the formula (XIX) and (XX) and isocyanates of the formula (XXI) and carbamic acid chlorides of the formula (XXII) are generally known compounds organic or inorganic chemistry.
Das Verfahren (A) ist dadurch gekennzeichnet, daß man Verbindungen der Formel (II), in welcher A, B, D, X, n und R8 die oben angegebenen Bedeutungen haben, in Gegenwart von Basen einer intramolekularen Kondensation unterwirft. Process (A) is characterized in that compounds of the formula (II) in which A, B, D, X, n and R 8 have the meanings given above are subjected to an intramolecular condensation in the presence of bases.
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (A) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sindAll inert organic solvents can be used as diluents in process (A) according to the invention. Are preferably usable
Kohlenwasserstoffe, wie Toluol und Xylol, ferner Ether, wie Dibutylether, Tetrahydrofuran, Dioxan, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N- Methyl-pyrrolidon, sowie Alkohole wie Methanol, Ethanol, Propanol, Iso- Propanol, Butanol, lso-Butanol und tert.-Butanol. Hydrocarbons, such as toluene and xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and alcohols, such as methanol, ethanol, propanol, isopropanol , Butanol, isobutanol and tert-butanol.
Als Basen (Deprotonierungsmittel) können bei der Durchführung des erfindungsgemäßen Verfahrens (A) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetall- und Erdalkalimetalloxide, -hydroxide und -carbonate, wie Natriumhydroxid, Kaliumhydroxid, Magnesiumoxid, Calciumoxid, Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat, die auch in Gegenwart von Phasentransferkatalysatoren wie z.B. Triethylbenzylammoniumchlorid, Tetrabutylammoniumbromid, Adogen 464 (= Methyltrialkyl(C8-C10)ammonium- chlorid) oder TDA 1 (= Tris-(methoxyethoxyethyl)-amin) eingesetzt werden können. Weiterhin können Alkalimetalle wie Natrium oder Kalium verwendet werden Ferner sind Alkalimetall- und Erdalkalimetallamide und -hydride, wie Natriumamid, Natriumhydrid und Calciumhydrid, und außerdem auch Alkalimetallalkoholate, wie Natrium-methylat, Natrium-ethylat und Kalium-tert.-butylat einsetzbar.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (A) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 50°C und 150°C. Das erfindungsgemäße Verfahren (A) wird im allgemeinen unter Normaldruck durchgeführt. All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (A) according to the invention. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 - C 10 ) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine) can be used. Furthermore, alkali metals such as sodium or potassium can be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used. When carrying out process (A) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. Process (A) according to the invention is generally carried out under normal pressure.
Bei der Durchführung des erfindungsgemäßen Verfahrens (A) setzt man die Reaktionskomponenten der Formel (II) und die deprotonierenden Basen im allgemeinen in etwa doppeltäquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 3 Mol) zu verwenden. When carrying out process (A) according to the invention, the reaction components of the formula (II) and the deprotonating bases are generally employed in approximately double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
Das Verfahren (B) ist dadurch gekennzeichnet, daß Verbindungen der Formel (III), in welcher A, B, X, n und R8 die oben angegebenen Bedeutungen haben, in Gegenwart einer Base und eines Verdünnungsmittels einer intramolekularen Kondensation unterwirft. Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (B) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, ferner Ether, wie Dibutylether, Tetrahydrofuran, Dioxan, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N- Methyl-pyrrolidon. Weiterhin können Alkohole wie Methanol, Ethanol, Propanol,Process (B) is characterized in that compounds of the formula (III) in which A, B, X, n and R 8 have the meanings given above are subjected to intramolecular condensation in the presence of a base and a diluent. All inert organic solvents can be used as diluents in process (B) according to the invention. Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol,
Iso-Propanol, Butanol, Iso-Butanol und tert.-Butanol eingesetzt werden. Iso-propanol, butanol, iso-butanol and tert-butanol can be used.
Als Basen (Deprotonierungsmittel) können bei der Durchführung des erfindungsgemäßen Verfahrens (B) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetall- und Erdalkalimetalloxide, -hydroxide und -carbonate, wie Natriumhydroxid, Kaliumhydroxid, Magnesiumoxid, Calciumoxid, Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat, die auch in Gegenwart von Phasentransferkatalysatoren wie z.B. Triethylbenzylammoniumchlorid, Tetrabutylammoniumbromid, Adogen 464 (= Methyltrialkyl(C8-C10)ammoniumchlorid) oder TDA 1 (= Tris-(methoxyethoxyethyl)-amin) eingesetzt werden können. Weiterhin können Alkalimetalle wie Natrium oder Kalium verwendet werden. Ferner sind Alkalimetall- und Erdalkalimetallamide und -hydride, wie Natriumamid, Natriumhydrid und Calciumhydrid, und außerdem auch Alkali
metallalkoholate, wie Natrium-methylat, Natrium-ethylat und Kalium-tert.-butylat einsetzbar. All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (B) according to the invention. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 - C 10 ) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine) can be used. Alkali metals such as sodium or potassium can also be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butoxide can be used.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (B) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischenThe reaction temperatures can be varied within a substantial range when carrying out process (B) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between
50°C und 150°C. 50 ° C and 150 ° C.
Das erfindungsgemäße Verfahren (B) wird im allgemeinen unter Normaldruck durchgeführt. Process (B) according to the invention is generally carried out under normal pressure.
Bei der Durchführung des erfindungsgemäßen Verfahrens (B) setzt man die Reaktionskomponenten der Formel (III) und die deprotonierenden Basen im allgemeinen in etwa doppeltäquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 3 Mol) zu verwenden. When carrying out process (B) according to the invention, the reaction components of the formula (III) and the deprotonating bases are generally employed in approximately double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
Das Verfahren (C) ist dadurch gekennzeichnet, daß man Verbindungen der Formel (IV) in welcher A, B, W, X, n und R die oben angegebene Bedeutung haben, inThe process (C) is characterized in that compounds of the formula (IV) in which A, B, W, X, n and R have the meaning given above, in
Gegenwart von Säuren und gegebenenfalls in Gegenwart eines Verdünnungsmittels intramolekular cyclisiert. In the presence of acids and optionally in the presence of a diluent cyclized intramolecularly.
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (C) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, ferner halogenierte Kohlenwasserstoffe wie Dichlormethan, Chloroform, Ethylenchlorid, Chlorbenzol, Dichlorbenzol, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N-Methyl-pyrrolidon. Weiterhin können Alkohole wie Methanol, Ethanol, Propanol, iso-Propanol, Butanol, Isobutanol, tert.-Butanol eingesetzt werden. All inert organic solvents can be used as diluents in process (C) according to the invention. Hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone are preferably used. Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
Gegebenenfalls kann auch die eingesetzte Säure als Verdünnungsmittel dienen. If necessary, the acid used can also serve as a diluent.
Als Säuren können bei dem erfindungsgemäßen Verfahren (C) alle üblichen anorganischen und organischen Säuren eingesetzt werden wie z.B. Halogenwasserstoffsäuren, Schwefelsäure, Alkyl-, Aryl- und Haloalkylsulfonsäuren, insbesondere halogenierte Alkylcarbonsäuren wie z.B. Trifluoressigsäure.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (C) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 50°C und 150°C. Das erfindungsgemäße Verfahren (C) wird im allgemeinen unter Normaldruck durchgeführt. Acids which can be used in process (C) according to the invention are all customary inorganic and organic acids, such as, for example, hydrohalic acids, sulfuric acid, alkyl-, aryl- and haloalkylsulfonic acids, in particular halogenated alkylcarboxylic acids such as trifluoroacetic acid. The reaction temperatures can be varied within a substantial range when carrying out process (C) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. Process (C) according to the invention is generally carried out under normal pressure.
Bei der Durchfuhrung des erfindungsgemäßen Verfahrens (C) setzt man die Reaktionskomponenten der Formeln (IV) und die Säure z.B. in äquimolaren Mengen ein. Es ist gegebenenfalls auch möglich, die Säure als Lösungsmittel oder als Katalysator zu verwenden. When carrying out process (C) according to the invention, the reaction components of the formulas (IV) and the acid, for example in equimolar amounts. It is optionally also possible to use the acid as a solvent or as a catalyst.
Die Verfahren (D-α) und (D-ß) sind dadurch gekennzeichnet, daß man Verbindungen der Formeln (V) oder (VI), in welchen X, R8, n und Hal die oben angegebenen Bedeutungen haben und Verbindungen der Formel (VII), in welcher A und D die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels einer Kondensation unterwirft. The processes (D-α) and (D-ß) are characterized in that compounds of the formulas (V) or (VI) in which X, R 8 , n and Hal have the meanings indicated above and compounds of the formula ( VII), in which A and D have the meanings given above, optionally in the presence of a base and optionally in the presence of a diluent, a condensation.
Als Verdünnungsmittel können bei den erfindungsgemäßen Verfahren (D-α) und (D-ß) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, ferner Ether, wie Dibutylether, Tetrahydrofuran, Dioxan, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N-Methyl-pyrrolidon. All inert organic solvents can be used as diluents in the processes (D-α) and (D-β) according to the invention. Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
Als Basen (Deprotonierungsmittel) können bei der Durchführung des erfindungsgemäßen Verfahrens (D-α) und (D-ß) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetall- und Erdalkalimetalloxide,All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (D-α) and (D-β). Alkali metal and alkaline earth metal oxides are preferably usable,
-hydroxide und -carbonate, wie Natriumhydroxid, Kaliumhydroxid, Magnesiumoxid, Calciumoxid, Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat, die auch in Gegenwart von Phasentransferkatalysatoren wie z.B. Triethylbenzylammoniumchlorid, Tetrabutylammoniumbromid, Adogen 464 (= Methyltrialkyl(C8- C10)ammoniumchlorid) oder TDA 1 (= Tris-(methoxyethoxyethyl)-amin) eingesetzt werden können. Weiterhin können Alkalimetalle wie Natrium oder Kalium verwendet werden. Ferner sind Alkalimetall- und Erdalkalimetallamide und -hydride,
wie Natriumamid, Natriumhydrid und Calciumhydrid, und außerdem auch Alkalimetallalkoholate, wie Natrium-methylat, Natrium-ethylat und Kalium-tert.-butylat einsetzbar. hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 - C 10 ) ammonium chloride) or TDA 1 (= Tris (methoxyethoxyethyl) amine) can be used. Alkali metals such as sodium or potassium can also be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can be used.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (D-α) und (D-ß) innerhalb eines größeren Bereiches variiert werden.The reaction temperatures can be varied within a substantial range when carrying out process (D-α) and (D-β) according to the invention.
Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und 250°C, vorzugsweise zwischen 0°C und 150°C. In general, temperatures between -20 ° C and 250 ° C, preferably between 0 ° C and 150 ° C.
Die erfindungsgemäßen Verfahren (D-α) und (D-ß) werden im allgemeinen unter Normaldruck durchgeführt. Bei der Durchführung der erfindungsgemäßen Verfahren (D-α) und (D-ß) setzt man die Reaktionskomponenten der Formeln (V) und (VII) oder (VI) und (VII) und die gegebenenfalls eingesetzte deprotonierenden Basen im allgemeinen in etwa äquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 3 Mol) zu verwenden. Das erfindungsgemäße Verfahren (E) ist dadurch gekennzeichnet, daß man Carbonylverbindungen der Formel (VIII) mit Ketensäurehalogeniden der Formel (II) in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Saureakzeptors umsetzt. The processes (D-α) and (D-β) according to the invention are generally carried out under normal pressure. When carrying out the processes (D-α) and (D-β) according to the invention, the reaction components of the formulas (V) and (VII) or (VI) and (VII) and the deprotonating bases which may be used are generally employed in approximately equimolar amounts on. However, it is also possible to use one or the other component in a larger excess (up to 3 moles). Process (E) according to the invention is characterized in that carbonyl compounds of the formula (VIII) are reacted with ketonic acid halides of the formula (II) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.
Als Verdünnungsmittel können hierbei alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol undAll inert organic solvents can be used as diluents. Hydrocarbons such as toluene and
Xylol, ferner Ether, wie Dibutylether, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N-Methyl-pyrrolidon. Xylene, also ethers, such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
Als Säureakzeptoren können bei der Durchführung des erfindungsgemäßen Verfahrens E) alle üblichen Säureakzeptoren verwendet werden. All customary acid acceptors can be used as acid acceptors when carrying out process E) according to the invention.
Vorzugsweise verwendbar sind tertiäre Amine, wie Triethylamin, Pyridin, Diazabicyclooctan (DABCO), Diazabicycloundecan (DBU), Diazabicyclononen (DBN), Hunig-Base und N,N-Dimethylanilin
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens E) innerhalb eines größeren Bereiches variiert werden. Zweckmäßigerweise arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 50°C und 220°C. Das Verfahren E) wird zweckmäßigerweise unter Normaldruck durchgeführt. Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline can preferably be used When carrying out process E) according to the invention, the reaction temperatures can be varied within a substantial range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C. Process E) is advantageously carried out under normal pressure.
Bei der Durchführung des erfindungsgemäßen Verfahrens E) setzt man die Reaktionskomponenten der Formeln (VIII) und (V), in welchen A, D, X und n die oben angegebenen Bedeutungen haben und Hal für Halogen steht, und gegebenenfalls die Säureakzeptoren zweckmäßigerweise in etwa äquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 5 Mol) zu verwenden. When carrying out process E) according to the invention, the reaction components of the formulas (VIII) and (V), in which A, D, X and n have the meanings given above and Hal represents halogen, and, if appropriate, the acid acceptors are expediently approximately equimolar Quantities. However, it is also possible to use one or the other component in a larger excess (up to 5 mol).
Das erfindungsgemäße Verfahren (F) ist dadurch gekennzeichnet, daß man Thioamide der Formel (IX) mit Ketensäurehalogeniden der Formel (V) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säureakzeptors umsetzt. Process (F) according to the invention is characterized in that thioamides of the formula (IX) are reacted with ketonic acid halides of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Als Verdünnungsmittel können beim Verfahren F) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, femer Ether, wie Dibutylether, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N-Methyl-pyrrolidon. All inert organic solvents can be used as diluents in process F). Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone are preferably usable.
Als Säureakzeptoren können alle üblichen Säureakzeptoren verwendet werden. All customary acid acceptors can be used as acid acceptors.
Vorzugsweise verwendbar sind tertiäre Amine, wie Triethylamin, Pyridin, Diazabicyclooctan (DABCO), Diazabicycloundecan (DBU), Diazabicyclononen (DBN), Hünig-Base und N,N-Dimethyl-anilin. Die Reaktionstemperaturen können innerhalb eines größeren Bereiches variiert werden. Zweckmäßigerweise arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 20°C und 220°C. Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can preferably be used. The reaction temperatures can be varied within a substantial range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 20 ° C and 220 ° C.
Das Verfahren F) wird zweckmäßigerweise unter Normaldruck durchgeführt.
Bei der Durchführung des erfindungsgemäßen Verfahrens F) setzt man die Reaktionskomponenten der Formeln (IX) und (V), in welchen A, X und n die oben angegebenen Bedeutungen haben und Hal für Halogen steht und gegebenenfalls die Säureakzeptoren zweckmäßigerweise in etwa äquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 5 Mol) zu verwenden. Process F) is advantageously carried out under normal pressure. When carrying out process F) according to the invention, the reaction components of the formulas (IX) and (V) in which A, X and n have the meanings indicated above and Hal represents halogen and, if appropriate, the acid acceptors are advantageously employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 5 mol).
Das Verfahren (G) ist dadurch gekennzeichnet, daß man Verbindungen der Formel (X), in welcher A, B, D, Q1, X, n und R8 die oben angegebene Bedeutung haben, in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels einer intramolekularen Kondensation unterwirft. The process (G) is characterized in that compounds of the formula (X) in which A, B, D, Q 1 , X, n and R 8 have the meaning given above, in the presence of a base and optionally in the presence of a Diluent undergoes intramolecular condensation.
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (G) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, ferner Ether, wie Dibutylether, Tetrahydrofuran, Dioxan, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N- Methyl-pyrrolidon. Weiterhin können Alkohole wie Methanol, Ethanol, Propanol, iso-Propanol, Butanol, Isobutanol, tert.-Butanol eingesetzt werden. All inert organic solvents can be used as diluents in process (G) according to the invention. Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
Als Basen (Deprotonierungsmittel) können bei der Durchführung des erfindungsgemäßen Verfahrens (G) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetall- und Erdalkalimetalloxide, -hydroxide und -carbonate, wie Natriumhydroxid, Kaliumhydroxid, Magnesiumoxid, Calciumoxid, Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat, die auch in Gegenwart von Phasentransferkatalysatoren wie z.B. Triethylbenzylammoniumchlorid, Tetrabutylammoniumbromid, Adogen 464 (Methyltrialkyl(C8-C10)ammoniumchlorid) oder TDA 1 (Tris-(methoxyethoxyethyl)-amin) eingesetzt werden können.All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (G) according to the invention. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used.
Weiterhin können Alkalimetalle wie Natrium oder Kalium verwendet werden. Ferner sind Alkalimetall- und Erdalkalimetallamide und -hydride, wie Natriumamid, Natriumhydrid und Calciumhydrid, und außerdem auch Alkalimetall-alkoholate, wie Natrium-methylat, Natrium-ethylat und Kalium-tert.-butylat einsetzbar. Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßenAlkali metals such as sodium or potassium can also be used. In addition, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used. The reaction temperatures can be carried out when carrying out the process according to the invention
Verfahrens (G) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 50°C und 150°C.
Das erfindungsgemäße Verfahren (G) wird im allgemeinen unter Normaldruck durchgeführt. Process (G) can be varied within a wide range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. Process (G) according to the invention is generally carried out under normal pressure.
Bei der Durchführung des erfindungsgemäßen Verfahrens (G) setzt man die Reaktionskomponenten der Formel (X) und die deprotonierenden Basen im allgemeinen in etwa äquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 3 Mol) zu verwenden. When carrying out process (G) according to the invention, the reaction components of the formula (X) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
Das Verfahren (H) ist dadurch gekennzeichnet, daß man Verbindungen der Formel (XI), in welcher A, B, D, Q1, Q2, Q3, X, n und R8 die oben angegebene Bedeutung haben, in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels einer intramolekularen Kondensation unterwirft. The process (H) is characterized in that compounds of the formula (XI) in which A, B, D, Q 1 , Q 2 , Q 3 , X, n and R 8 have the meaning given above, in the presence of a Base and optionally in the presence of a diluent, an intramolecular condensation.
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (H) alle inerten organischen Solventien eingesetzt werden. Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Toluol und Xylol, ferner Ether, wie Dibutylether, Tetrahydrofuran, Dioxan, Glykoldimethylether und Diglykoldimethylether, außerdem polare Lösungsmittel, wie Dimethylsulfoxid, Sulfolan, Dimethylformamid und N- Methyl-pyrrolidon. Weiterhin können Alkohole wie Methanol, Ethanol, Propanol, iso-Propanol, Butanol, Isobutanol, tert.-Butanol eingesetzt werden. All inert organic solvents can be used as diluents in process (H) according to the invention. Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
Als Basen (Deprotonierungsmittel) können bei der Durchführung des erfindungsgemäßen Verfahrens (H) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetall- und Erdalkalimetalloxide, -hydroxide und -carbonate, wie Natriumhydroxid, Kaliumhydroxid, Magnesiumoxid, Calciumoxid, Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat, die auch in Gegenwart von Phasentransferkatalysatoren wie z.B. Triethylbenzylammoniumchlorid, Tetrabutylammoniumbromid, Adogen 464 (Methyltrialkyl(C8-C10)ammoniumchlorid) oder TDA 1 (Tris-(methoxyethoxyethyl)-amin) eingesetzt werden können. Weiterhin können Alkalimetalle wie Natrium oder Kalium verwendet werden. Ferner sind Alkalimetall- und Erdalkalimetallamide und -hydride, wie Natriumamid, Natriumhydrid und Calciumhydrid, und außerdem auch Alkalimetall-alkoholate, wie Natrium-methylat, Natrium-ethylat und Kalium-tert.-butylat einsetzbar. All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (H) according to the invention. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, also in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C 8 -C 10 ) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used. Alkali metals such as sodium or potassium can also be used. In addition, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (H) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen
arbeitet man bei Temperaturen zwischen 0°C und 250°C, vorzugsweise zwischen 50°C und 150°C The reaction temperatures can be varied within a substantial range when carrying out process (H) according to the invention. In general one works at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C
Das erfindungsgemäße Verfahren (H) wird im allgemeinen unter Normaldruck durchgeführt. Bei der Durchführung des erfindungsgemäßen Verfahrens (H) setzt man dieProcess (H) according to the invention is generally carried out under normal pressure. When carrying out process (H) according to the invention, the
Reaktionskomponenten der Formel (XI) und die deprotonierenden Basen im allgemeinen in etwa äquimolaren Mengen ein. Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 3 Mol) zu verwenden. Das Verfahren (Iα) ist dadurch gekennzeichnet, daß man Verbindungen derReaction components of the formula (XI) and the deprotonating bases generally in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles). The process (Iα) is characterized in that compounds of
Formeln (I-1-a) bis (I-8-a) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Saurebindemittels mit Carbonsaurehalogeniden der Formel (XII) umsetzt Reacting formulas (I-1-a) to (I-8-a) with carboxylic acid halides of the formula (XII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
Als Verdünnungsmittel können bei dem erfindungsgemaßen Verfahren (Iα) alle gegenüber den Säurehalogeniden inerten Solventien eingesetzt werden Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Benzin, Benzol, Toluol, Xylol und Tetralin, ferner Halogenkohlenwasserstoffe, wie Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol und o-Dichlorbenzol, außerdem Ketone, wie Aceton und Methylisopropylketon, weiterhin Ether, wie Diethylether, Tetrahydrofuran und Dioxan, darüber hinaus Carbonsaureester, wie Ethylacetat, und auch stark polare Solventien, wie Dimethylsulfoxid und Sulfolan Wenn die Hydrolysestabilitat des Saurehalogenids es zulaßt, kann die Umsetzung auch in Gegenwart von Wasser durchgeführt werden Diluents which can be used in process (Iα) according to the invention are all solvents which are inert to the acid halides. Hydrocarbons, such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, can preferably be used. in addition ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of Water
Als Saurebindemittel kommen bei der Umsetzung nach dem erfindungsgemäßen Verfahren (Iα) alle üblichen Saureakzeptoren in Betracht Vorzugsweise verwendbar sind tertiäre Amine, wie Triethylamin, Pyridin, Diazabicyclooctan (DABCO), Diazabicycloundecen (DBU), Diazabicyclononen (DBN), Hunig-Base und N,N-Dimethyl-anilin, ferner Erdalkahmetalloxide, wie Magnesium- und Calciumoxid, außerdem Alkali- und Erdalkali-metall-carbonate, wie Natriumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalihydroxide wie Natriumhydroxid undSuitable acid binders for the reaction according to process (Iα) according to the invention are all customary acid acceptors. Tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, can preferably be used. N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, furthermore alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides such as sodium hydroxide and
Kaliumhydroxid
Die Reaktionstemperaturen können auch bei dem erfindungsgemäßen Verfahren (Iα) innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +150°C, vorzugsweise zwischen 0°C und 100°C. Bei der Durchführung des erfindungsgemäßen Verfahrens (Iα) werden die Ausgangsstoffe der Formeln (I-1-a) bis (I-8-a) und das Carbonsäurehai ogenid der Formel (XII) im allgemeinen in angenähert äquivalenten Mengen verwendet. Es ist jedoch auch möglich, das Carbonsäurechlorid in einem größeren Überschuß (bis zu 5 Mol) einzusetzen. Die Aufarbeitung erfolgt nach üblichen Methoden. Das Verfahren (Iß) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels mit Carbonsäureanhydriden der Formel (XIII) umsetzt. Potassium hydroxide The reaction temperatures can also be varied within a substantial range in process (Iα) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C. When carrying out process (Iα) according to the invention, the starting materials of the formulas (I-1-a) to (I-8-a) and the carboxylic acid shauride of the formula (XII) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid chloride in a larger excess (up to 5 mol). The processing takes place according to usual methods. Process (Iß) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted with carboxylic anhydrides of the formula (XIII), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (Iß) vorzugsweise diejenigen Verdünnungsmittel verwendet werden, die auch bei derDiluents which can be used in the process (Iß) according to the invention are preferably those diluents which are also suitable for
Verwendung von Säurehai ogeniden vorzugsweise in Betracht kommen. Im übrigen kann auch ein im Überschuß eingesetztes Carbonsäureanhydrid gleichzeitig als Verdünnungsmittel fungieren. Use of acid shark ogeniden preferably come into consideration. Otherwise, an excess of carboxylic acid anhydride can also act as a diluent.
Die Reaktionstemperaturen können bei dem erfindungsgemäßen Verfahren (Iß) auch bei der Verwendung von Carbonsäureanhydriden innerhalb eines größerenThe reaction temperatures in the process (Iß) according to the invention can also be used within a relatively large range when using carboxylic anhydrides
Bereiches variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +150°C, vorzugsweise zwischen 0°C und 100°C. Range can be varied. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
Bei der Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe der Formeln (I-1-a) bis (I-8-a) und das Carbonsäureanhydrid der Formel (XIII) im allgemeinen in angenähert äquivalenten Mengen verwendet. Es ist jedoch auch möglich, das Carbonsäureanhydrid in einem größeren Überschuß (bis zu 5 Mol) einzusetzen. Die Aufarbeitung erfolgt nach üblichen Methoden. When carrying out the process according to the invention, the starting materials of the formulas (I-1-a) to (I-8-a) and the carboxylic anhydride of the formula (XIII) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
Im allgemeinen geht man so vor, daß man Verdünnungsmittel und im Überschuß vorhandenes Carbonsäureanhydrid sowie die entstehende Carbonsäure durch Destillation oder durch Waschen mit einem organischen Lösungsmittel oder mitIn general, the procedure is such that diluent and excess carboxylic anhydride and the resulting carboxylic acid are obtained by distillation or by washing with an organic solvent or with
Wasser entfernt.
Das Verfahren (J) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Saurebindemittels mit Chlorameisensaureestern oder Chlorameisensaurethiolestern der Formel (XIV) umsetzt Als Saurebindemittel kommen bei der Umsetzung nach dem erfindungsgemäßenWater removed. Process (J) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, with chloroformates or chloroformates of formula (XIV) Acid binders used in the reaction according to the invention
Verfahren (J) alle üblichen Saureakzeptoren in Betracht Vorzugsweise verwendbar sind tertiäre Amine, wie Triethylamin, Pyridin, DABCO, DBU, DBA, Hünig-Base und N,N-Dimethyl-anilin, ferner Erdalkalimetalloxide, wie Magnesium- und Calciumoxid, außerdem Alkali- und Erdalkalimetallcarbonate, wie Natrium carbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalihydroxide wie Natriumhydroxid und Kaliumhydroxid Process (J) all customary acid acceptors into consideration. Tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide
Als Verdünnungsmittel können bei dem erfindungsgemäßen Verfahren (J) alle gegenüber den Chlorameisensaureestern bzw. Chlorameisensaurethiolestern inerten Solventien eingesetzt werden Vorzugsweise verwendbar sind Kohlenwasserstoffe, wie Benzin, Benzol, Toluol, Xylol und Tetralin, ferner Halogenkohlenwasserstoffe, wie Methylenchlorid, Chloroform, Tetrachlorkohlenwasserstoff, Chlorbenzol und o-Dichlorbenzol, außerdem Ketone, wie Aceton und Methylisopropylketon, weiterhin Ether, wie Diethylether, Tetrahydrofuran und Dioxan, darüber hinaus Carbonsaureester, wie Ethylacetat, und auch stark polare Solventien, wie Dimethylsulfoxid und Sulfolan Diluents which can be used in process (J) according to the invention are all solvents which are inert to the chloroformic acid esters or chloroformic acid urethiol esters. Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o -Dichlorobenzene, also ketones, such as acetone and methyl isopropyl ketone, further ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane
Die Reaktionstemperaturen bei der Durchfuhrung des erfindungsgemäßen Verfahrens (J) innerhalb eines größeren Bereiches variiert werden Arbeitet man in Gegenwart eines Verdünnungsmittels und eines Saurebindemittels, so liegen die Reaktionstemperaturen im allgemeinen zwischen -20°C und +100°C, vorzugsweise zwischen 0°C und 50°C The reaction temperatures in carrying out process (J) according to the invention can be varied within a substantial range. If one works in the presence of a diluent and an acid binder, the reaction temperatures are generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C
Das erfindungsgemaße Verfahren (J) wird im allgemeinen unter Normaldruck durchgeführt Process (J) according to the invention is generally carried out under normal pressure
Bei der Durchfuhrung des erfindungsgemaßen Verfahrens (J) werden die Ausgangsstoffe der Formeln (I-1-a) bis (I-8-a) und der entsprechende Chlorameisensaureester bzw Chlorameisensaurethiolester der Formel (XIV) im allgemeinen in angenähert äquivalenten Mengen verwendet Es ist jedoch auch möglich, die eine oder andere Komponente in einem größeren Überschuß (bis zu 2 Mol)
einzusetzen. Die Aufarbeitung erfolgt dann nach üblichen Methoden Im allgemeinen geht man so vor, daß man ausgefallene Salze entfernt und das verbleibende Reaktionsgemisch durch Abziehen des Verdünnungsmittels einengt When carrying out process (J) according to the invention, the starting materials of the formulas (I-1-a) to (I-8-a) and the corresponding chloroformate or chloroformate diol ester of the formula (XIV) are generally used in approximately equivalent amounts also possible, one or the other component in a larger excess (up to 2 mol) to use. The working up is then carried out by customary methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent
Das erfindungsgemäße Verfahren (K) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) mit (Kα) Verbindungen der FormelThe process (K) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with (Kα) compounds of the formula
(XV) in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels oder (Kß) Schwefelkohlenstoff und anschließend mit Alkylhalogeniden der Formel (XVI) umsetzt (XV) in the presence of a diluent and optionally in the presence of an acid binder or (Kß) carbon disulfide and then reacted with alkyl halides of the formula (XVI)
Beim Herstellungsverfahren (Kα) setzt man pro Mol Ausgangsverbindung der Formeln (I- 1-a) bis (I-8-a) ca. 1 Mol Chlormonothioameisensäureester bzw. Chlordithioameisensaureester der Formel (XV) bei 0 bis 120°C, vorzugsweise bei 20 bis 60°C um In the preparation process (Kα), about 1 mol of chloromothio formate or chlorodithio formate of formula (XV) is used at 0 to 120 ° C., preferably at 20, per mol of starting compound of the formulas (I-1-a) to (I-8-a) up to 60 ° C
Als gegebenenfalls zugesetzte Verdünnungsmittel kommen alle inerten polaren organischen Losungsmittel in Frage, wie Ether, Amide, Sulfone, Sulfoxide, aber auch Halogenalkane Possible diluents added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also haloalkanes
Vorzugsweise werden Dimethylsulfoxid, Tetrahydrofuran, Dimethylformamid oder Methylenchlorid eingesetzt Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used
Stellt man in einer bevorzugten Ausfuhrungsform durch Zusatz von starken Deprotonierungsmitteln wie z.B. Natriumhydrid oder Kaliumtertiärbutylat das Enolatsalz der Verbindungen (I-1-a) bis (I-8-a) dar, kann auf den weiteren Zusatz von Saurebindemitteln verzichtet werden If you put in a preferred embodiment by adding strong deprotonating agents such as Sodium hydride or potassium tert-butylate, the enolate salt of the compounds (I-1-a) to (I-8-a), can be dispensed with the further addition of acid binders
Werden Saurebindemittel eingesetzt, so kommen übliche anorganische oder organische Basen in Frage, beispielhaft seien Natriumhydroxid, Natriumcarbonat, Kahumcarbonat, Pyridin und Triethylamin aufgeführt Die Reaktion kann bei Normaldruck oder unter erhöhtem Druck durchgeführt werden, vorzugsweise wird bei Normaldruck gearbeitet Die Aufarbeitung geschieht nach üblichen Methoden If acid binders are used, customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine. The reaction can be carried out under atmospheric pressure or under elevated pressure, preferably under atmospheric pressure. Working up is carried out by customary methods
Beim Herstellungsverfahren (Kβ) setzt man pro Mol Ausgangsverbindungen der Formeln (I-1-a) bis (I-8-a) die aquimolare Menge bzw einen Überschuß Schwefel
kohlenstoff zu. Man arbeitet hierbei vorzugsweise bei Temperaturen von 0 bis 50°C und insbesondere bei 20 bis 30°C. In the production process (Kβ), the molar amount or an excess of sulfur is used per mole of starting compounds of the formulas (I-1-a) to (I-8-a) carbon too. The process is preferably carried out at temperatures from 0 to 50 ° C. and in particular at 20 to 30 ° C.
Oft ist es zweckmäßig zunächst aus den Verbindungen der Formeln (I-1-a) bis (I-8-a) durch Zusatz einer Base (wie z.B. Kaliumtertiärbutylat oder Natriumhydrid) das entsprechende Salz herzustellen. Man setzt die Verbindungen (I-1-a) bis (I-8-a) solange mit Schwefelkohlenstoff um, bis die Bildung der Zwischenverbindung abgeschlossen ist, z.B. nach mehrstündigem Rühren bei Raumtemperatur. It is often expedient first to prepare the corresponding salt from the compounds of the formulas (I-1-a) to (I-8-a) by adding a base (such as, for example, potassium tert-butoxide or sodium hydride). Compounds (I-1-a) to (I-8-a) are reacted with carbon disulfide until the formation of the intermediate compound is complete, e.g. after stirring for several hours at room temperature.
Als Basen können beim Verfahren (Kß) alle üblichen Protonenakzeptoren eingesetzt werden. Vorzugsweise verwendbar sind Alkalimetallhydride, Alkalimetallalkoholate, Alkali- oder Erdalkalimetallcarbonate oder -hydrogencarbonate oderAll conventional proton acceptors can be used as bases in the process (Kß). Alkali metal hydrides, alkali metal alcoholates, alkali metal or alkaline earth metal carbonates or bicarbonates or are preferably usable
Stickstoffbasen. Genannt seien beispielsweise Natriumhydrid, Natriummethanolat, Natriumhydroxid, Calciumhydroxid, Kahumcarbonat, Natriumhydrogencarbonat, Triethylamin, Dibenzylamin, Diisopropylamin, Pyridin, Chinolin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) und Diazabicycloundecen (DBU) Als Verdünnungsmittel können bei diesem Verfahren alle üblichen Lösungsmittel verwendet werden. Nitrogen bases. Examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU). Common solvents can be used as diluents in this process .
Vorzugsweise sind verwendbar aromatische Kohlenwasserstoffe wie Benzol oder Toluol, Alkohole wie Methanol, Ethanol, Isopropanol oder Ethyl englykol, Nitrile wie Acetonitril, Ether wie Tetrahydrofuran oder Dioxan, Amide wie Dimethylformamid oder andere polare Lösungsmittel wie Dimethylsulfoxid oder Sulfolan. Aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethyl englycol, nitriles such as acetonitrile, ethers such as tetrahydrofuran or dioxane, amides such as dimethylformamide or other polar solvents such as dimethyl sulfoxide or sulfolane can preferably be used.
Die weitere Umsetzung mit dem Alkylhalogenid der Formel (XVI) erfolgt vorzugsweise bei 0 bis 70°C und insbesondere bei 20 bis 50°C. Hierbei wird mindestens die aquimolare Menge Alkylhalogenid eingesetzt. The further reaction with the alkyl halide of the formula (XVI) is preferably carried out at 0 to 70 ° C. and in particular at 20 to 50 ° C. Here, at least the equimolar amount of alkyl halide is used.
Man arbeitet bei Normaldruck oder unter erhöhtem Druck, vorzugsweise bei Normaldruck. One works at normal pressure or under increased pressure, preferably at normal pressure.
Die Aufarbeitung erfolgt wiederum nach üblichen Methoden. The processing is again carried out using customary methods.
Das erfindungsgemäße Verfahren (L) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) mit Sulfonsäurechloriden der Formel
(XVII) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt. Process (L) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with sulfonic acid chlorides of the formula (XVII) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Beim Herstellungsverfahren (L) setzt man pro Mol Ausgangsverbindung der Formel (I-1-a bis I-8-a) ca. 1 Mol Sulfonsäurechlorid (XVII) bei -20 bis 150°C, vorzugsweise bei 20 bis 70°C um. In the production process (L), about 1 mol of sulfonic acid chloride (XVII) is reacted at -20 to 150 ° C., preferably at 20 to 70 ° C., per mole of starting compound of the formula (I-1-a to I-8-a).
Als gegebenenfalls zugesetzte Verdünnungsmittel kommen alle inerten polaren organischen Lösungsmittel in Frage wie Ether, Amide, Nitrile, Sulfone, Sulfoxide oder halogenierte Kohlenwasserstoffe wie Methylenchlorid. Possible diluents added are all inert polar organic solvents such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
Vorzugsweise werden Dimethylsulfoxid, Tetrahydrofuran, Dimethylformamid, Methylenchlorid eingesetzt. Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
Stellt man in einer bevorzugten Ausführungsform durch Zusatz von starken Deprotonierungsmitteln (wie z.B. Natriumhydrid oder Kaliumtertiärbutylat) das Enolatsalz der Verbindungen (I-1-a) bis (I-8-a) dar, kann auf den weiteren Zusatz von Säurebindemitteln verzichtet werden. Werden Säurebindemittel eingesetzt, so kommen übliche anorganische oder organische Basen in Frage, beispielhaft seien Natriumhydroxid, Natriumcarbonat, Kaliumcarbonat, Pyridin, Triethylamin aufgeführt. If, in a preferred embodiment, the enolate salt of the compounds (I-1-a) to (I-8-a) is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tert-butoxide), the further addition of acid binders can be dispensed with. If acid binders are used, customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
Die Reaktion kann bei Normaldruck oder unter erhöhtem Druck durchgeführt werden, vorzugsweise wird bei Normaldruck gearbeitet. Die Aufarbeitung geschieht nach üblichen Methoden. The reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure. The processing takes place according to usual methods.
Das erfindungsgemäße Verfahren (M) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) mit Phosphorverbindungen der Formel (XVIII) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt Beim Herstellungsverfahren (M) setzt man zum Erhalt von Verbindungen derProcess (M) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) are reacted with phosphorus compounds of the formula (XVIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder Manufacturing process (M) is used to obtain compounds of
Strukturen (I-1-e) bis (I-8-e) auf 1 Mol der Verbindungen (I-1-a) bis (I-8-a), 1 bis 2, vorzugsweise 1 bis 1 ,3 Mol der Phosphorverbindung der Formel (XVIII) bei Temperaturen zwischen -40°C und 150°C, vorzugsweise zwischen -10 und 1 10°C um.
Als gegebenenfalls zugesetzte Verdünnungsmittel kommen aller inerten, polaren organischen Lösungsmittel in Frage wie Ether, Amide, Nitrile, Carbonsäureester, Sulfide, Sulfone, Sulfoxide etc. Structures (I-1-e) to (I-8-e) on 1 mol of the compounds (I-1-a) to (I-8-a), 1 to 2, preferably 1 to 1, 3 mol of the phosphorus compound of the formula (XVIII) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 1 10 ° C. Any inert, polar organic solvents such as ethers, amides, nitriles, carboxylic acid esters, sulfides, sulfones, sulfoxides, etc. are suitable as diluents which may be added.
Vorzugsweise werden Acetonitril, Dimethylsulfoxid, Tetrahydrofuran, Dimethylformamid oder Methylenchlorid eingesetzt. Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
Als gegebenenfalls zugesetzte Säurebindemittel kommen übliche anorganische oder organische Basen in Frage wie Hydroxide, Carbonate oder Amine. Beispielhaft seien Natriumhydroxid, Natriumcarbonat, Kaliumcarbonat, Pyridin und Triethylamin aufgeführt. Die Umsetzung kann bei Normaldruck oder unter erhöhtem Druck durchgeführt werden, vorzugsweise wird bei Normaldruck gearbeitet. Die Aufarbeitung geschieht nach üblichen Methoden der organischen Chemie. Die Reinigung der anfallenden Endprodukte geschieht vorzugsweise durch Kristallisation, chromatographische Reinigung oder durch sogenanntes "Andestillieren", d.h. Entfernung der flüchtigen Bestandteile im Vakuum. Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine. The reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure. The processing takes place according to the usual methods of organic chemistry. The end products obtained are preferably purified by crystallization, chromatographic purification or by so-called "distillation", i.e. Removal of volatiles in vacuo.
Das Verfahren (N) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) mit Metallhydroxiden bzw. Metallalkoxiden der Formel (XIX) oder Aminen der Formel (XX), gegebenenfalls in Gegenwart eines Verdünnungsmittels, umsetzt. Als Verdünnungsmittel können vorzugsweise Ether wie Tetrahydrofuran, Dioxan,Process (N) is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with metal hydroxides or metal alkoxides of the formula (XIX) or amines of the formula (XX), if appropriate in the presence of a diluent. Preferred diluents are ethers such as tetrahydrofuran, dioxane,
Diethylether oder aber Alkohole wie Methanol, Ethanol, Isopropanol, aber auch Wasser eingesetzt werden. Das erfindungsgemäße Verfahren (N) wird im allgemeinen unter Normaldruck durchgeführt. Die Reaktionstemperaturen liegen im allgemeinen zwischen -20°C und 100°C, vorzugsweise zwischen 0°C und 50°C. Das erfindungsgemäße Verfahren (O) ist dadurch gekennzeichnet, daß man Verbindungen der Formeln (I-1-a) bis (I-8-a) mit (Oα) Verbindungen der Formel (XXI) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators oder (Oß) mit Verbindungen der Formel (XXII) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt.
Bei Herstellungsverfahren (Oα) setzt man pro Mol Ausgangsverbindung der Formeln (I-1-a) bis (I-8-a) ca. 1 Mol Isocyanat der Formel (XXI) bei 0 bis 100°C, vorzugsweise bei 20 bis 50°C um Diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water can be used. Process (N) according to the invention is generally carried out under normal pressure. The reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C. Process (O) according to the invention is characterized in that compounds of the formulas (I-1-a) to (I-8-a) with (Oα) compounds of the formula (XXI), if appropriate in the presence of a diluent and if appropriate in the presence of a Reacting catalyst or (Oß) with compounds of formula (XXII) optionally in the presence of a diluent and optionally in the presence of an acid binder. In production process (Oα), about 1 mol of isocyanate of the formula (XXI) is used at 0 to 100 ° C., preferably at 20 to 50 °, per mole of starting compound of the formulas (I-1-a) to (I-8-a) C um
Als gegebenenfalls zugesetzte Verdünnungsmittel kommen alle inerten organischen Losungsmittel in Frage, wie Ether, Amide, Nitrile, Sulfone oder Sulfoxide Possible diluents added are all inert organic solvents, such as ethers, amides, nitriles, sulfones or sulfoxides
Gegebenenfalls können Katalysatoren zur Beschleunigung der Reaktion zugesetzt werden. Als Katalysatoren können sehr vorteilhaft zinnorganische Verbindungen, wie z B. Dibutylzinndilaurat eingesetzt werden. Es wird vorzugsweise bei Normaldruck gearbeitet Beim Herstellungsverfahren (Oß) setzt man pro Mol Ausgangsverbindung der Formeln (I-1-a) bis (I-8-a) ca 1 Mol Carbamidsaurechlorid der Formel (XXII) bei 0 bis 150°C, vorzugsweise bei 20 bis 70°C um If necessary, catalysts can be added to accelerate the reaction. Organotin compounds, such as dibutyltin dilaurate, can be used very advantageously as catalysts. It is preferably carried out at normal pressure. In the preparation process (Oß), about 1 mol of carbamic acid chloride of the formula (XXII) at 0 to 150 ° C., preferably, is used per mole of starting compound of the formulas (I-1-a) to (I-8-a) at 20 to 70 ° C
Als gegebenenfalls zugesetzte Verdünnungsmittel kommen alle inerten polaren organischen Losungsmittel in Frage wie Ether, Amide, Nitrile, Carbonsaureester, Sulfone, Sulfoxide oder halogenierte Kohlenwasserstoffe Possible diluents added are all inert polar organic solvents, such as ethers, amides, nitriles, carboxylic acid esters, sulfones, sulfoxides or halogenated hydrocarbons
Die erfindungsgemaßen Wirkstoffe eignen sich zur Bekämpfung von tierischen Schädlingen, vorzugsweise Arthropoden und Nematoden, insbesondere Insekten und Spinnentieren, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksamThe active compounds according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector.They are resistant to normally sensitive and resistant species and to all or individual stages of development
Zu den oben erwähnten Schädlingen gehören The pests mentioned above include
Aus der Ordnung der Isopoda z B Oniscus asellus, Armadillidium vulgäre, Porcellio scaber From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber
Aus der Ordnung der Diplopoda z B Blaniulus guttulatus From the order of the Diplopoda, for example, Blaniulus guttulatus
Aus der Ordnung der Chilopoda z B Geophilus carpophagus, Scutigera spec From the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec
Aus der Ordnung der Symphyla z B Scutigerella immaculata From the order of the Symphyla eg Scutigerella immaculata
Aus der Ordnung der Thysanura z B Lepisma saccharina From the order of the Thysanura, for example Lepisma saccharina
Aus der Ordnung der Collembola z B Onychiurus armatus
Aus der Ordnung der Orthoptera z.B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria, Supella spp.. Aus der Ordnung der Dermaptera z.B. Forficula auricularia. From the order of the Collembola, for example Onychiurus armatus From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria, Supella spp .. From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Reticulitermes spp.. From the order of the Isoptera e.g. Reticulitermes spp ..
Aus der Ordnung der Anoplura z.B. Phylloxera vastatrix, Pemphigus spp., Phthirus spp., Pediculus spp., Haematopinus spp., Linognathus spp., Solenopotes spp.. From the order of the anoplura e.g. Phylloxera vastatrix, Pemphigus spp., Phthirus spp., Pediculus spp., Haematopinus spp., Linognathus spp., Solenopotes spp ..
Aus der Ordnung der Mallophaga z.B. Trichodectes spp., Damalinea spp., Trimenopon spp., Monopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp., Trimenopon spp., Monopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,
Lepikentron spp., Felicola spp.. Lepikentron spp., Felicola spp ..
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci. Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp., Panstrongylus spp.. From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci. From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp., Panstrongylus spp ..
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp. From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis, spp. Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella,Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella,
Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
Aus der Ordnung der Coleoptera z.B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilus surinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodalazaisyo spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,
Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica. Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agrebri molitor, Tenebrio molitor. Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.
Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Muscina spp.. From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp. , Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Simulium spp., Eusimulium spp., Phlebia spp. , Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Muscina spp. .
Aus der Ordnung der Siphonapterida z.B. Xenopsylla spp., Ceratophyllus spp., Pulex spp., Ctenocephalides spp.. From the order of the Siphonapterida e.g. Xenopsylla spp., Ceratophyllus spp., Pulex spp., Ctenocephalides spp ..
Aus der Ordnung der Arachnida z.B. Scorpio maurus, Latrodectus mactans. From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
Aus der Ordnung der Acarina z.B. Myocoptes spp., Otodectes spp., Acarus siro, Argas spp., Ornithodoros spp., Ornithonyssus spp., Dermanyssus spp., Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,From the order of the Acarina e.g. Myocoptes spp., Otodectes spp., Acarus siro, Argas spp., Ornithodoros spp., Ornithonyssus spp., Dermanyssus spp., Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommommas spp spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,
Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,
Dermacentor spp., Haemaphysalis spp., Raillietia spp., Pneumonyssus spp., Sternostorma spp., Varroa spp.. Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Dermacentor spp., Haemaphysalis spp., Raillietia spp., Pneumonyssus spp., Sternostorma spp., Varroa spp ..
Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B.: Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example: Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. , Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Die erfindungsgemäßen Wirkstoffe zeichnen sich durch eine hohe insektizide und akarizide Wirksamkeit aus. The active compounds according to the invention are notable for high insecticidal and acaricidal activity.
Sie lassen sich mit besonders gutem Erfolg beispielsweise zur Bekämpfung der Bohnenspinnmilbe verwenden. They can be used with particularly good results, for example, to control the spider bean mite.
Die erfindungsgemäßen Wirkstoffe können weiterhin als Defoliants, Desiccants, Krautabtötungsmittel und insbesondere als Unkrautvernichtungsmittel verwendet werden. Unter Unkraut im weitesten Sinne sind alle Pflanzen zu verstehen, die anThe active compounds according to the invention can furthermore be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that are on
Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewendeten Menge ab. Growing up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen ver- wendet werden: The active compounds according to the invention can e.g. can be used for the following plants:
Dikotyle Unkräter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotola, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduusanum, Sonch , Rotola, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Taraxacum. Ranunculus, Taraxacum.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Iochasumum, Pasum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Sachharum, Ananas, Asparagus, Allium. Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Sachharum, Pineapple, Asparagus, Allium.
Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen. However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
Die Verbindunngen eignen sich in Abhängigkeit von der Konzentration zur Totalunkrautbekämpfung z.B. auf Industrie- und Gleisanlagen und auf Wegen und Plätzen mit und ohne Baumbewuchs. Ebenso können die Verbindungen zur Unkrautbekämpfung in Dauerkulturen, z.B. Forst, Ziergehölz-, Obst, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen, auf Zier- und Sportrasen und Weideflächen und zur selektiven Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden. Depending on the concentration, the compounds are suitable for total weed control e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control be used in annual crops.
Die erfindungsgemäßen Wirkstoffe eignen sich sehr gut zur selektiven Bekämpfung monokotyler Unkräuter in dikotylen Kulturen im Vor- und Nachlaufverfahren. Sie können beispielsweise in Baumwolle oder Zuckerrüben mit sehr gutemThe active compounds according to the invention are very well suited for the selective control of monocotyledon weeds in dicotyledon crops in the pre- and post-process. You can, for example, in cotton or sugar beet with very good
Erfolg zur Bekämpfung von Schadgräser eingesetzt werden. Success can be used to control harmful grass.
Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymerenThe active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers
Stoffen. Substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols , such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage: The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schäum erzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen¬ e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene
Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfäte, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose. Fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used. The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien,In its commercially available formulations and in the use forms prepared from these formulations, the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants,
Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, chlorierte Kohlenwasserstoffe, Phenylharnstoffe, durch Mikroorganismen hergestellte Stoffe u.a. Besonders günstige Mischpartner sind z.B. die folgenden: Bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides are present. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc. Particularly cheap mixing partners are e.g. the following:
Fungizide: Fungicides:
2-Aminobutan; 2-Anilino-4-methyl-6-cyclopropyl-pyrimidin; 2',6'-Dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazol-5-carboxaniIid; 2,6-Dichloro-N-(4-trifluoromethy1benzy1)-benzamid; (E)-2-Methoxyimino-N-methyI-2-(2- phenoxyphenyl)-acetamid; 8-Hydroxyquinolinsulfat; Methyl-(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylat; Methyl-(E)-methoximino- [alpha-(o-tolyloxy)-o-tolyl]acetat; 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazol, 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxaniide; 2,6-dichloro-N- (4-trifluoromethy1benzy1) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat (Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenylamin, Dipyrithion, Ditalimfos, Dithianon, Dodine, Drazoxolon, Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, Epoxyconazole, Ethirimol, Etridiazol, Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil,
Flutriafol, Folpet, Fosetyl-Aluminium, Fthalide, Fuberidazol, Furalaxyl , Furmecyclox, Flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox,
Guazatine, Guazatine,
Hexachlorobenzol, Hexaconazol, Hymexazol,
lmazalil, Imibenconazol, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan, Kasugamycin, Kupfer-Zubereitungen, wie: Kupferhydroxid, Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mischung, Hexachlorobenzene, hexaconazole, hymexazole, lmazalil, imibenconazole, iminoctadine, Iprobefos (IBP), iprodione, isoprothiolan, kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil, Methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol, Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin, Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocarb, Pefurazoate, penconazole, pencycuron, phosdiphene, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb,
Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon,
Quintozen (PCNB), Quintozen (PCNB),
Schwefel und Schwefel-Zubereitungen, Sulfur and sulfur preparations,
Tebuconazol, Tecloftalam, Tecnazen, Tetraconazol, Thiabendazol, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon,
Triadimenol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin,Triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin,
Triticonazol, Triticonazole,
Validamycin A, Vinclozolin, Validamycin A, vinclozolin,
Zineb, Ziram. Bakterizide: Zineb, ziram. Bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen. Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide: Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinhrhrhrinhrhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrhrinhrhrinhrhrinhrhrinhrinhrofhrinophhrinhrinhrinhrinhrinhrinhrinhrinhrinhrhrinhrhrinhrinhrhrinhrhrinhrhrinhrhrinhrofhrine Cyhexatin, cypermethrin, cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon
HCH, Heptenophos, Hexaflumuron, Hexythiazox, HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram, Naled, NC 184, NI 25, Nitenpyram,
Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos, Quinalphos,
RH 5992, RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos,
Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox,Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox,
Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos,Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos,
Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Triazuron, trichlorfon, triflumuron, trimethacarb,
Vamidothion, XMC, Xylylcarb, YI 5301 / 5302, Zetamethrin. Herbizide: Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin. Herbicides:
beispielsweise Anilide, wie z.B. Diflufenican und Propanil; Arylcarbonsäuren, wie z.B. Dichlorpicolinsäure, Dicamba und Picloram; Aryloxy alkansäuren, wie z.B. 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP und Triclopyr; Aryloxy-phenoxy- alkansäureester, wie z.B. Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, e.g. anilides, e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxy alkanoic acids, e.g. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl,
Hal oxyfop-methyl und Quizalofop-ethyl; Azinone, wie z.B. Chloridazon undHal oxyfop-methyl and Quizalofop-ethyl; Azinones, e.g. Chloridazon and
Norflurazon; Carbamate, wie z.B Chlorpropham, Desmedipham, Phenmedipham
und Propham; Chloracetanilide, wie z.B. Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor und Propachlor; Dinitroaniline, wie z.B. Oryzalin, Pendimethalin und Trifluralin; Diphenylether, wie z.B. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen und Oxyfluorfen; Harnstoffe, wie z.B. Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron undNorflurazon; Carbamates, such as, for example, chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and
Methabenzthiazuron; Hydroxylamine, wie z.B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim und Tralkoxydim; Imidazolinone, wie z.B. Imazethapyr, Imazamethabenz, Imazapyr und Imazaquin; Nitrile, wie z.B. Bromoxynil, Dichlobenil und Ioxynil; Oxyacetamide, wie z.B. Mefenacet; Sulfonylharnstoffe, wie z.B. Amidosulfuron, Bensulfuron-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuronethyl, Thifensulfuron-methyl, Triasulfuron und Tribenuron-methyl; Thiolcarbamate, wie z.B. Butylate, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb und Triallate; Triazine, wie z.B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne und Terbutylazin; Triazinone, wie z.B. Hexazinon, Metamitron und Metribuzin; Sonstige, wie z.B. Aminotriazol, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate und Tridiphane. Der erfindungsgemäße Wirkstoff kann femer in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß. Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen. Methabenzthiazuron; Hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuronethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. Hexazinone, metamitron and metribuzin; Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane. The active ingredient according to the invention can furthermore be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. The application takes place in a customary manner adapted to the application forms.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe. Beispielsweise zeigen sie eine hervorragendeWhen used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates. The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. For example, they show excellent
Wirksamkeit gegen Zecken, wie beispielsweise Boophilus microplus. Efficacy against ticks, such as Boophilus microplus.
Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur Bekämpfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Bienen, sonstige Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere, wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfalle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so daß durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist. The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and reduced performance (for meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that more economical and simple animal husbandry is possible through the use of the active compounds according to the invention.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten Boli, des feed-through- Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie z.B. durchThe active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, paste boluses, the feed-through method, suppositories, by parenteral administration, such as e.g. by
Injektion (intramuskulär, subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot- on), des Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern,Injection (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb straps,
Halftern, Markierungsvorrichtungen usw. Halters, marking devices etc.
Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemischesWhen used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or as a chemical
Bad verwenden. Use bath.
Die Herstellung und die Verwendung der erfindungsgemäßen Stoffe wird durch die folgenden Beispiele veranschaulicht
Herstellungsbeispiele Beispiel I-1B-a-1 The preparation and use of the substances according to the invention is illustrated by the following examples Production Examples Example I-1B-a-1
15,52 g (0,14 Mol) Kalium-tert.-butylat (95 %ig) werden in 40 ml wasserfreiem Tetrahydrofuran vorgelegt. Unter Rückfluß wird eine Lösung von 18,6 g N-[2-(3- Methyl)-thienyl]-acetyl-piperidin-2-carbonsäureethylester gemäß Beispiel (II-1) in15.52 g (0.14 mol) of potassium tert-butoxide (95%) are placed in 40 ml of anhydrous tetrahydrofuran. A solution of 18.6 g of N- [2- (3-methyl) -thienyl] -acetyl-piperidine-2-carboxylic acid ethyl ester according to Example (II-1) is refluxed in
120 ml wasserfreiem Toluol zugetropft und 1,5 h unter Rückfluß weitergerührt.120 ml of anhydrous toluene were added dropwise and stirring was continued for 1.5 hours under reflux.
Nach Abkühlen wird das Reaktionsgemisch mit 170 ml Wasser versetzt, dieAfter cooling, the reaction mixture is mixed with 170 ml of water
Toluolphase abgetrennt und erneut mit 85 ml Wasser extrahiert. Die vereinigten wäßrigen Phasen werden bei 0 bis 10°C mit ca. 22 ml konzentrierter Salzsäure angesäuert, der Niederschlag abgesaugt und getrocknet. Auf diese Weise erhält man 14,3 g (Δ92 % d. Theorie) der oben gezeigten Verbindung vom Schmp.Toluene phase separated and extracted again with 85 ml of water. The combined aqueous phases are acidified at 0 to 10 ° C with about 22 ml of concentrated hydrochloric acid, the precipitate is suction filtered and dried. In this way, 14.3 g (Δ92% of theory) of the compound shown above are obtained from the melting point.
159°C. 159 ° C.
In analoger Weise zu Beispiel I-1 A-a-1 bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die in der Tabelle aufgeführten Substanzen der Formel I-1-a:
The substances of the formula I-1-a listed in the table are obtained analogously to Example I-1 Aa-1 or according to the general information on the preparation:
Beispiel I-1 B-b-1 Example I-1 B-b-1
Zu einer Lösung von 1,39 g (5 mmol) der Verbindung gemäß Beispiel I-1 B-a-3 in 50 ml Dichlormethan gibt man 0,51 g (5 mmol) Triethylamin und eine kleine Spatelspitze Diazabicyclooctan (DABCO). Anschließend tropft man bei 0°C bis 10°C 0,6 g (5 mmol) Pivalinsäurechlorid zu. Man läßt 15 min bei Raumtemperatur nachrühren, hydrolysiert mit 5 ml 10 % NaOH, trennt die Phasen und wäscht die organische Phase mit Wasser. Nach dem Trocknen über Magnesiumsulfat wird filtriert und eingedampft. 0.51 g (5 mmol) of triethylamine and a small spatula tip of diazabicyclooctane (DABCO) are added to a solution of 1.39 g (5 mmol) of the compound according to Example I-1 B-a-3 in 50 ml of dichloromethane. Then 0.6 g (5 mmol) of pivalic acid chloride is added dropwise at 0 ° C. to 10 ° C. The mixture is stirred for 15 min at room temperature, hydrolyzed with 5 ml of 10% NaOH, the phases are separated and the organic phase is washed with water. After drying over magnesium sulfate, the mixture is filtered and evaporated.
Ausbeute: 1,36 g (75 % d. Th.) brauner Feststoff vom Fp. 184°C. Yield: 1.36 g (75% of theory) of a brown solid, mp. 184 ° C.
Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die in der Tabelle 2 aufgeführten Verbindungen der Formel I-1-b:
The compounds of the formula I-1-b listed in Table 2 are obtained analogously or according to the general information on the preparation:
Beispiel I-1 BBc-1 Example I-1 BBc-1
Zu einer Lösung von 1,39 g (5 mmol) der Verbindung gemäß Beispiel I-l B-a-3 in 50 ml Dichlormethan werden 0,51 g (5 mmol) Triethylamin und eine kleine Spatelspitze DABCO gegeben. Anschließend werden bei 0 bis 10°C 0,61 g (5 mmol) Chlorameisensäureisopropylester in 5 ml Toluol zugetropft. Man läßt 15 min bei Raumtemperatur nachrühren. Weitere 1,0 ml 1,0 M Chlorameisensäureisopropylester in Toluol (= 0,12 g; 1,0 mmol) und 0,1 ml (0,1 g; 1,0 mmol) Triethylamin werden nachgesetzt. Nach weiteren 15 min Rühren bei Raumtemperatur wird mit 5 ml Wasser hydrolysiert, die organische Phase abgetrennt, über MgSO4 getrocknet, filtriert und eingeengt. 0.51 g (5 mmol) of triethylamine and a small spatula tip DABCO are added to a solution of 1.39 g (5 mmol) of the compound according to Example II Ba-3 in 50 ml of dichloromethane. Then 0.61 g (5 mmol) of isopropyl chloroformate in 5 ml of toluene are added dropwise at 0 to 10 ° C. The mixture is left to stir at room temperature for 15 minutes. A further 1.0 ml of 1.0 M isopropyl chloroformate in toluene (= 0.12 g; 1.0 mmol) and 0.1 ml (0.1 g; 1.0 mmol) of triethylamine are added. After stirring for a further 15 min at room temperature, the mixture is hydrolyzed with 5 ml of water, the organic phase is separated off, dried over MgSO 4 , filtered and concentrated.
Ausbeute. 1,58 g rotbrauner Feststoff (87 % d. Th.) vom Fp. 196°C. Yield. 1.58 g red-brown solid (87% of theory), mp. 196 ° C.
Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die folgenden Verbindungen der Formel I-1-c:
The following compounds of the formula I-1-c are obtained analogously or according to the general information on the preparation:
Beispiel I-1 B-g-1 Example I-1 B-g-1
Zu einer Lösung von 1,39 g (5 mmol) der Verbindung gemäß Beispiel I-1 B-a-3 in 50 ml Dichlormethan werden 0,51 g (5 mmol) Triethylamin und eine kleine Spatelspitze DABCO gegeben. Anschließend wird bei 0 bis 10°C 0,88 g (8,2 mmol) N,N-Dimethylcarbamoylchlorid zugetropft. Man läßt 15 min bei Raumtemperatur nachrühren, hydrolysiert mit 5 ml 10 % NaOH, trennt die Phasen und wäscht die organische Phase mit Wasser. Man trocknet über MgSO4, filtriert und engt ein. Das so erhaltene Rohprodukt wird mit Petrolether ausgerührt. Der lösliche Teil wird abdekantiert und eingedampft. 0.51 g (5 mmol) of triethylamine and a small spatula tip DABCO are added to a solution of 1.39 g (5 mmol) of the compound according to Example I-1 Ba-3 in 50 ml of dichloromethane. Then 0.88 g (8.2 mmol) of N, N-dimethylcarbamoyl chloride is added dropwise at 0 to 10 ° C. The mixture is stirred for 15 min at room temperature, hydrolyzed with 5 ml of 10% NaOH, the phases are separated and the organic phase is washed with water. It is dried over MgSO 4 , filtered and concentrated. The crude product thus obtained is extracted with petroleum ether. The soluble part is decanted off and evaporated.
Ausbeute: 1,70 g brauner Feststoff (98 % d.Th.) vom Fp. 122°C (Zersetzung).
Yield: 1.70 g of brown solid (98% of theory), mp 122 ° C. (decomposition).
Beispiel (I-2 B-a-1) Example (I-2 B-a-1)
Zu einer Lösung von 1 ,68 g (15 mmol) Kalium-tert.-butylat in 10 ml Dimethylformamid wird bei 0 bis 10°C eine Lösung von 3,0 g (9,68 mmol) der Verbindung gemäß Beispiel (III-B-1) in 10 ml Dimethylformamid getropft. Man läßt über Nacht unter Rühren auf Raumtemperatur kommen. Anschließend werden unter Kühlung 50 ml 1 N HCl zugetropft. Nach 15 Minuten wird der ausgefallene Niederschlag abgesaugt, gut mit Wasser gewaschen und getrocknet. Ausbeute 1,60 g (63 % der Theorie) hellgelbe Kristalle vom Fp. 237°C. 1H-NMR (CDCl3): 2,15 ppm (s, 3H, Thienyl-CH3), 6,91 ppm (d, 1H, 4- Thiophen-H, 3J = 5,1 Hz), 7,30 ppm (d, 1H, 5-Thiophen-H, 3J = 5,1 Hz) A solution of 3.0 g (9.68 mmol) of the compound according to Example (III-B.) Is added to a solution of 1.68 g (15 mmol) of potassium tert-butoxide in 10 ml of dimethylformamide at 0 to 10 ° C. -1) dropped in 10 ml of dimethylformamide. The mixture is allowed to come to room temperature overnight with stirring. 50 ml of 1N HCl are then added dropwise with cooling. After 15 minutes, the precipitate is filtered off, washed well with water and dried. Yield 1.60 g (63% of theory) of light yellow crystals, mp. 237 ° C. 1H-NMR (CDCl 3 ): 2.15 ppm (s, 3H, thienyl-CH 3 ), 6.91 ppm (d, 1H, 4-thiophene-H, 3 J = 5.1 Hz), 7.30 ppm (d, 1H, 5-thiophene-H, 3J = 5.1 Hz)
GC/MS (SIL): 89,9 % (Index 2271; MS: 336 (M +), 246, 218, 203, 190, GC / MS (SIL): 89.9% (index 2271; MS: 336 (M + ), 246, 218, 203, 190,
109, 73, 45)
109, 73, 45)
Beispiel (I-2 A-a-2) Example (I-2 A-a-2)
Analog Beispiel (I-2 B-a-1) erhält man ausgehend von der Verbindung gemäß Beispiel (III-A-2) die oben gezeigte Verbindung als hellgelbe Kristalle vom Fp. 239°C (Zers.). 1H-NMR (CDCl3): 2,30 ppm (s, 3H, Thienyl-CH3), 2,41 ppm (s, 3H, Thienyl- CH3), 6,59 ppm (s, 1H, 4-Thiophen-H Analogously to Example (I-2 Ba-1), starting from the compound according to Example (III-A-2), the compound shown above is obtained as pale yellow crystals with a melting point of 239 ° C. (dec.). 1 H-NMR (CDCl 3 ): 2.30 ppm (s, 3H, thienyl-CH 3 ), 2.41 ppm (s, 3H, thienyl-CH 3 ), 6.59 ppm (s, 1H, 4- Thiophene-H
MS: 278 (M+), 260, 178, 152, 109 MS: 278 (M + ), 260, 178, 152, 109
Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die folgenden Verbindungen der Formel I-2-a:
The following compounds of the formula I-2-a are obtained analogously or according to the general information on the preparation:
Beispiel (I-2 B-b-1) Example (I-2 B-b-1)
Zu einer Lösung von 1,0 g (3,79 mmol) der Verbindung gemäß Beispiel (I-2 B-a-1) in 10 ml Tetrahydrofuran gibt man insgesamt 0,48 g (4,8 mmol) Triethylamin, 0,40 g (5,1 mmol) Acetylchlorid und eine kleine Spatelspitze Diazabicycloundecen (DABCO) und rührt insgesamt etwa 2 Tage bei Raumtemperatur. Dann wird mit Diethylether verdünnt und mit Wasser salzfrei gewaschen. Nach dem Trocknen wird im Vakuum eingeengt. Ausbeute: 1,0 g (86 % der Theorie), Fp. 203°C. Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die folgenden Verbindungen der Formel I-b-2:
To a solution of 1.0 g (3.79 mmol) of the compound according to Example (I-2 Ba-1) in 10 ml of tetrahydrofuran is added a total of 0.48 g (4.8 mmol) of triethylamine, 0.40 g ( 5.1 mmol) of acetyl chloride and a small spatula tip of diazabicycloundecene (DABCO) and stirred for a total of about 2 days at room temperature. Then it is diluted with diethyl ether and washed salt-free with water. After drying, the mixture is concentrated in vacuo. Yield: 1.0 g (86% of theory), mp. 203 ° C. The following compounds of the formula Ib-2 are obtained analogously or according to the general information on the preparation:
Beispiel (I-2 B-c-1) Example (I-2 Bc-1)
Zu einer Lösung von 1,0 g (3,79 mmol) der Verbindung gemäß Beispiel (I-2 B-a-1) in 10 ml Tetrahydrofuran gibt man 0,38 g (3,8 mmol) Triethylamin und eine kleine Spatelspitze DABCO. Anschließend werden bei Raumtemperatur 0,47 g (3,8 mmol) Chlorameisensäureisopropylester zugetropft. Nach Rühren über Nacht bei Raumtemperatur wird mit Diethylether verdünnt und mit Wasser salzfrei gewaschen, getrocknet und eingeengt. To a solution of 1.0 g (3.79 mmol) of the compound according to Example (I-2 B-a-1) in 10 ml of tetrahydrofuran are added 0.38 g (3.8 mmol) of triethylamine and a small spatula tip DABCO. Then 0.47 g (3.8 mmol) of isopropyl chloroformate are added dropwise at room temperature. After stirring overnight at room temperature, the mixture is diluted with diethyl ether and washed salt-free with water, dried and concentrated.
Ausbeute: 1,40 g (85 % d.Th.) Öl. 1H-NMR (CDCl3): 1,17 ppm (d, 6H, -OCH(CH3)2, 3J = 6,3 Hz), 2,18 ppm (s, Yield: 1.40 g (85% of theory) of oil. 1H-NMR (CDCl 3 ): 1.17 ppm (d, 6H, -OCH (CH 3 ) 2 , 3 J = 6.3 Hz), 2.18 ppm (s,
3H, Thienyl-CH3), 4,76 ppm (m, 1H, -OCH(CH3)2), 6,87 ppm (d, 1H, 4-Thiophen-H, 3J = 5,1 Hz), 7,33 ppm (d, 1H, 5-Thiophen-H, 3J = 5,1 Hz) 3H, thienyl-CH 3 ), 4.76 ppm (m, 1H, -OCH (CH 3 ) 2 ), 6.87 ppm (d, 1H, 4-thiophene-H, 3 J = 5.1 Hz), 7.33 ppm (d, 1H, 5-thiophene-H, 3 J = 5.1 Hz)
GC/MS (SIL): 81,4 % (Index 2343; MS: 350 (M+), 264, 241, 219, 164, GC / MS (SIL): 81.4% (index 2343; MS: 350 (M + ), 264, 241, 219, 164,
109, 43) 109, 43)
Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die folgenden Verbindungen der Formel I-2-c:
The following compounds of the formula I-2-c are obtained analogously or according to the general information on the preparation:
Herstellung der Ausgangsstoffe Beispiel (II-B-1) Production of the starting materials Example (II-B-1)
Eine Lösung von 11,1 g der Verbindung gemäß Beispiel (XXIV-1) in 50 ml Tetrahydrofuran (THF) tropft man bei 0°C bis 10°C zu einer Mischung ausA solution of 11.1 g of the compound according to Example (XXIV-1) in 50 ml of tetrahydrofuran (THF) is added dropwise to a mixture at 0 ° C. to 10 ° C.
10,1 ml Piperidin-2-carbonsäureethylester und 9 ml (0,641 Mol) Triethylamin in 100 ml THF. Man rührt 1 Stunde bei Raumtemperatur, saugt ab, wäscht mit THF nach und dampft ein. Der Rückstand wird in CH2Cl2 aufgenommen, mit 0.5 N HCl gewaschen, getrocknet und eingedampft. 10.1 ml of ethyl piperidine-2-carboxylate and 9 ml (0.641 mol) of triethylamine in 100 ml of THF. The mixture is stirred at room temperature for 1 hour, filtered off, washed with THF and evaporated. The residue is taken up in CH 2 Cl 2 , washed with 0.5 N HCl, dried and evaporated.
Ausbeute: 18,6 g (95 % d. Th.) braunes Öl. Yield: 18.6 g (95% of theory) of a brown oil.
Analog zu Beispiel (II-B-1) wurden folgende Verbindungen der Formel (II) erhalten:
The following compounds of the formula (II) were obtained analogously to Example (II-B-1):
Beispiel (III-B-1) Example (III-B-1)
Zu einer Lösung von 6,90 g (39,5 mmol) der Verbindung gemäß Beispiel (XXIV)-1 in 60 ml Dichlormethan tropft man bei Raumtemperatur 6,88 g (40 mmol) 1-Hydroxycyclohexancarbonsäureethylester und rührt über Nacht unter Rückfluß. Nach dem Einengen wird der Rückstand über Kieselgel (mit Petrolether/Aceton 9/1) Chromatographien. Ausbeute 7,80 g (63 % der Theorie) Öl. 1H-NMR (CDCI3): 2,21 ppm (s, 3H, Thienyl-CH3), 3 ,77 ppm (s, 2H, At room temperature, 6.88 g (40 mmol) of ethyl 1-hydroxycyclohexane carboxylate are added dropwise to a solution of 6.90 g (39.5 mmol) of the compound according to Example (XXIV) -1 in 60 ml of dichloromethane and the mixture is stirred under reflux overnight. After concentration, the residue is chromatographed on silica gel (with petroleum ether / acetone 9/1). Yield 7.80 g (63% of theory) of oil. 1H-NMR (CDCI 3 ): 2.21 ppm (s, 3H, thienyl-CH 3 ), 3.77 ppm (s, 2H,
Thienyl-CH2-), 6,82 ppm (d, 1H, 4-Thiophen-H, 3J = 5,1 Hz), 7,10 ppm (d, 1H, 5-Thiophen-H, 3J = 5,1 Hz) Thienyl-CH 2 -), 6.82 ppm (d, 1H, 4-thiophene-H, 3 J = 5.1 Hz), 7.10 ppm (d, 1H, 5-thiophene-H, 3 J = 5 , 1 Hz)
GC/MS (SIL): 70,2 % (Index 2016; MS: 310 (M+), 155, 138, 1 1 1, 81, 29)
GC / MS (SIL): 70.2% (index 2016; MS: 310 (M + ), 155, 138, 1 1 1, 81, 29)
Beisniel (III-A-2) Example (III-A-2)
Analog erhält man die oben gezeigte Verbindung (III-A-2). 1H-NMR (CDCl3): 3,50 ppm (s, 2H, Thienyl-CH2-), 6,55 ppm (d, 1H, 4- Thiophen-H) The compound shown above (III-A-2) is obtained analogously. 1H-NMR (CDCl 3 ): 3.50 ppm (s, 2H, thienyl-CH 2 -), 6.55 ppm (d, 1H, 4-thiophene-H)
GC/MS (SIL): 38,0 % (Index 2074; MS: 324 (M +), 169, 152, 125, 81) GC / MS (SIL): 38.0% (index 2074; MS: 324 (M + ), 169, 152, 125, 81)
Analog zu den Beispielen (III-B-1) und (III-A-2) wurden folgende Verbindungen der Formel (III) erhalten:
The following compounds of the formula (III) were obtained analogously to Examples (III-B-1) and (III-A-2):
ie Verbindungen in der Tabelle fielen als braune Öle an.
Beispiel (XXIV-1) The compounds in the table were obtained as brown oils. Example (XXIV-1)
Zu einer Lösung von 6,30 g (40,4 mmol) der Verbindung der Formel To a solution of 6.30 g (40.4 mmol) of the compound of the formula
in 50 ml Dichlormethan tropft man bei Raumtemperatur 6,1 g (48 mmol) Oxalylchlorid. Man rührt über Nacht und engt dann im Vakuum ein. Ausbeute 6,90 g (99 % der Theorie) Öl. 6.1 g (48 mmol) of oxalyl chloride are added dropwise at room temperature in 50 ml of dichloromethane. The mixture is stirred overnight and then concentrated in vacuo. Yield 6.90 g (99% of theory) of oil.
Das so erhaltene Rohprodukt wurde nicht weiter gereinigt.
The crude product thus obtained was not further purified.
Beispiel (XXX-1) Example (XXX-1)
Eine Lösung der Verbindung gemäß Beispiel (XXXII-1) in 500 ml 10 % wäßriger KOH wird 3 Stunden zum Rückfluß erhitzt. Nach Abkühlen wird mit Wasser verdünnt und unter Eiskühlung mit konzentrierter Salzsäure angesäuert. Die wäßrige Lösung wird mehrmals mit Dichlormethan extrahiert; die organische Phase wird über MgSO4 getrocknet und filtriert. Anschließend wird das Lösungsmittel im Vakuum entfernt. A solution of the compound according to Example (XXXII-1) in 500 ml of 10% aqueous KOH is heated to reflux for 3 hours. After cooling, it is diluted with water and acidified with concentrated hydrochloric acid while cooling with ice. The aqueous solution is extracted several times with dichloromethane; the organic phase is dried over MgSO 4 and filtered. The solvent is then removed in vacuo.
Ausbeute: 35,0 g orangefarbene Kristalle (95 % der Theorie). 1H-NMR (CDCl3): 2,18 ppm (s, 3H, Thienyl-CH3), 3,77 ppm (s, 2H, Thienyl- CH2-), 6,83 ppm (d, 1H, 4-Thiophen-H, 3J = 5,1 Hz), 7,13 ppm (d, 1H, 5-Thiophen-H, 3J = 5,1 Hz).
Yield: 35.0 g of orange crystals (95% of theory). 1H-NMR (CDCl 3 ): 2.18 ppm (s, 3H, thienyl-CH 3 ), 3.77 ppm (s, 2H, thienyl-CH 2 -), 6.83 ppm (d, 1H, 4- Thiophene-H, 3 J = 5.1 Hz), 7.13 ppm (d, 1H, 5-thiophene-H, 3 J = 5.1 Hz).
Beispiel (XXXII-1) Example (XXXII-1)
46,1 g (0,587 Mol) Acetylchlorid werden unter Eiskühlung in 500 ml Methanol getropft. Zur so erhaltenen Lösung tropft man bei Raumtemperatur eine Lösung von 56,0 g (0,191 Mol) der Verbindung der Formel 46.1 g (0.587 mol) of acetyl chloride are added dropwise to 500 ml of methanol while cooling with ice. A solution of 56.0 g (0.191 mol) of the compound of the formula is added dropwise to the solution thus obtained at room temperature
in 100 ml Methanol. Man rührt über Nacht bei Raumtemperatur, engt ein, nimmt den Rückstand in Ether auf und wäscht mehrmals mit wäßriger Natriumhydrogencarbonatlösung. Die organische Phase wird anschließend getrocknet und eingeengt. Ausbeute: 35,0 g oranges Öl (100 % der Theorie, bezogen auf 3-Methyl-2-thiophencarbaldehyd). 1H-NMR (CDCl3): 2, 1 8 ppm (s, 3H, Thienyl-CH3), 3 ,71 ppm (s, 3H, in 100 ml of methanol. The mixture is stirred overnight at room temperature, concentrated, the residue is taken up in ether and washed several times with aqueous sodium bicarbonate solution. The organic phase is then dried and concentrated. Yield: 35.0 g of orange oil (100% of theory, based on 3-methyl-2-thiophenecarbaldehyde). 1H-NMR (CDCl 3 ): 2.18 ppm (s, 3H, thienyl-CH 3 ), 3.71 ppm (s, 3H,
-COOCH3), 3,74 ppm (s, 2H, Thienyl-CH2-), 6,82 ppm (d, 1H, 4-Thiophen-H, 3J = 5,1 Hz), 7,1 1 ppm (d, 1H, 5- Thiophen-H, 3J = 5,1 Hz).
-COOCH 3 ), 3.74 ppm (s, 2H, thienyl-CH 2 -), 6.82 ppm (d, 1H, 4-thiophene-H, 3 J = 5.1 Hz), 7.1 1 ppm (d, 1H, 5-thiophene-H, 3 J = 5.1 Hz).
Herstellung des für Beispiel (XXXII-1) benötigten Vorprodukts Preparation of the preliminary product required for example (XXXII-1)
Zur Lösung von 27,9 g (0,200 Mol) 3-Methyl-2-thiophencarbaldehyd in 80 ml trockenem Tetrahydrofuran werden 37,5 g (0,300 Mol) Methyl-methylmercaptomethyl-sulfoxid und 134 g (0,320 Mol) Benzyltrimethylammoniumhydroxid, 40 % in37.5 g (0.300 mol) of methyl methyl mercaptomethyl sulfoxide and 134 g (0.320 mol) of benzyltrimethylammonium hydroxide, 40% in, are dissolved in 27.9 g (0.200 mol) of 3-methyl-2-thiophenecarbaldehyde in 80 ml of dry tetrahydrofuran
MeOH (= Triton B), gegeben. Nach 14-stündigem Erhitzen unter Rückfluß wird eingeengt. Der verbleibende Rückstand wird in Dichlormethan aufgenommen und zweimal mit je 100 ml IN Schwefelsäure gewaschen. Die organische Phase wird getrocknet, filtriert und im Vakuum eingedampft. MeOH (= Triton B). After refluxing for 14 hours, the mixture is concentrated. The remaining residue is taken up in dichloromethane and washed twice with 100 ml IN sulfuric acid. The organic phase is dried, filtered and evaporated in vacuo.
Ausbeute: 56,0 g dunkelbraune Flüssigkeit (Rohprodukt). Yield: 56.0 g of dark brown liquid (crude product).
GC/MS: 71,5 % Isomer A (Index 1964); MS: 232 (M+), 169, 153, 121 GC / MS: 71.5% isomer A (index 1964); MS: 232 (M + ), 169, 153, 121
7,6 % Isomer B (Index 1991); MS: 232 (M+), 169, 154, 141
7.6% isomer B (index 1991); MS: 232 (M + ), 169, 154, 141
Beispiel (XXX-2) Example (XXX-2)
69,0 g (270 mMol) 2,5-Dimethyl-3-thienylessigsäurethiomorpholinid in 147 ml 50 % wäßriger NaOH und 500 ml Methanol p.a. werden 5 Stunden unter Rückfluß erhitzt. Nach dem Abdestillieren des Methanols wird mit Wasser verdünnt und mit verdünnter Salzsäure angesäuert. Der so erhaltene schmierige Feststoff wird abgesaugt, nochmals in Dichlormethan aufgenommen und über Magnesiumsulfat getrocknet. Die wäßrige Phase wird mehrmals mit Dichlormethan extrahiert, die vereinigten organischen Phasen werden nach Trocknen über Magnesiumsulfat eingeengt. Zur weiteren Reinigung wird der Rückstand in 10 %iger NaOH gelöst, mit69.0 g (270 mmol) of 2,5-dimethyl-3-thienylacetic acid thiomorpholinide in 147 ml of 50% aqueous NaOH and 500 ml of methanol p.a. are heated under reflux for 5 hours. After the methanol has been distilled off, it is diluted with water and acidified with dilute hydrochloric acid. The greasy solid thus obtained is suction filtered, taken up again in dichloromethane and dried over magnesium sulfate. The aqueous phase is extracted several times with dichloromethane, and the combined organic phases are concentrated after drying over magnesium sulfate. For further purification, the residue is dissolved in 10% NaOH with
Ether extrahiert, anschließend mit verdünnter Salzsäure angesäuert, mit Dichlormethan extrahiert, getrocknet, filtriert und eingeengt. Extracted ether, then acidified with dilute hydrochloric acid, extracted with dichloromethane, dried, filtered and concentrated.
Ausbeute: 36,0 g brauner Feststoff (78 % der Theorie). 1H-NMR (CDCl3): 2,32 ppm (s, 3H, Thienyl-CH3), 2,39 ppm (s, 3H, Tienyl- CH3), 3,50 ppm (s, 2H, Thienyl-CH2-), 6,55 ppm (s, 1H, 4- Thiophen-H). Yield: 36.0 g of brown solid (78% of theory). 1H-NMR (CDCl 3 ): 2.32 ppm (s, 3H, thienyl-CH 3 ), 2.39 ppm (s, 3H, tienyl-CH 3 ), 3.50 ppm (s, 2H, thienyl-CH) 2 -), 6.55 ppm (s, 1H, 4-thiophene-H).
GC/MS (SIL): 93 % (Index 1434); MS; 242 (M+; SIL), 227, 198, 125, 125, GC / MS (SIL): 93% (index 1434); MS; 242 (M + ; SIL), 227, 198, 125, 125,
73, 45.
73, 45.
,5-Dimethyl-3-thienylessigsäurethioιnorpholinid , 5-Dimethyl-3-thienylessigsäurethioιnorpholinid
10,0 g (64,8 mMol) 3-Acetyl-2,5-dimethylthiophen, 13,0 ml (13,0 g; 149 mMol) Morpholin und 3,49 g (109 mMol) Schwefel werden 16 Stunden unter Rückfluß erhitzt. Nach dem Erkalten wird auf 20 ml Ethanol gegossen, eingeengt, mit Wasser versetzt und mit Dichlormethan extrahiert. Nach Trocknen über Magnesiumsulfat, Filtrieren und Einengen erhält man 16,6 g Öl, das durch Säulenchromatographie an Kieselgel mit Dichlormethan/Essigester 1 : 1 gereinigt wird. 10.0 g (64.8 mmol) of 3-acetyl-2,5-dimethylthiophene, 13.0 ml (13.0 g; 149 mmol) of morpholine and 3.49 g (109 mmol) of sulfur are heated under reflux for 16 hours . After cooling, it is poured onto 20 ml of ethanol, concentrated, mixed with water and extracted with dichloromethane. After drying over magnesium sulfate, filtering and concentrating, 16.6 g of oil are obtained, which is purified by column chromatography on silica gel with dichloromethane / ethyl acetate 1: 1.
Ausbeute: 12,5 g rotbrauner Feststoff (75 % der Theorie). 1H-NMR (CDCl3): 2,30 ppm (s, 3H, Thienyl-CH3), 2,37 ppm (s, 3H, Thienyl- CH3), 3,46 ppm (m, 2H, Morpholin-CH2), 3,59 ppm (m, 2H,Yield: 12.5 g of red-brown solid (75% of theory). 1 H-NMR (CDCl 3 ): 2.30 ppm (s, 3H, thienyl-CH 3 ), 2.37 ppm (s, 3H, thienyl-CH 3 ), 3.46 ppm (m, 2H, morpholine- CH 2 ), 3.59 ppm (m, 2H,
Morpholin-CH2), 3,76 ppm (m, 2H, Morpholin-CH2), 4,09 ppm (s, 2H, Thienyl-CH2-), 4,37 ppm (m, 2H, Morpholin- CH2), 6,60 ppm (s, 1H, 4-Thiophen-H). Morpholine-CH 2 ), 3.76 ppm (m, 2H, morpholine-CH 2 ), 4.09 ppm (s, 2H, thienyl-CH 2 -), 4.37 ppm (m, 2H, morpholine-CH 2) ), 6.60 ppm (s, 1H, 4-thiophene-H).
GC/MS: 85 % (Index 2113); MS: 255 (M+), 222, 168, 125, 86, 59, GC / MS: 85% (index 2113); MS: 255 (M + ), 222, 168, 125, 86, 59,
28.
28th
Anwendungsbeispiel Beispiel A Example of use Example A
Tetranychus-Test (OP-resistent/Spritzbehandlung) Tetranychus test (OP-resistant / spray treatment)
Lösungsmittel: 3 Gewichtsteile Dimethylformamid Solvent: 3 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil Alkylarylpolyglykolether Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Bohnenpflanzen (Phaseolus vulgaris), die stark von allen Entwicklungsstadien der gemeinen Spinnmilbe oder Bohnenspinnmilbe (Tetranychus urticae) befallen sind, werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt. To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration. Bean plants (Phaseolus vulgaris), which are severely affected by all stages of development of the common spider mite or bean spider mite (Tetranychus urticae), are treated by dipping into the active compound preparation of the desired concentration.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Spinnmilben abgetötet wurden; 0 % bedeutet, daß keine Spinnmilben abgetötet wurden. After the desired time, the kill is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
In diesem Test bewirkten z.B. die Verbindungen gemäß Herstellungsbeispielen I-2 Ba-1 und I-2 Bc-1 bei einer beispielhaften Wirkstoffkonzentration von 0,1 % eine Abtötung von mindestens 98 % nach 7 Tagen.
In this test, for example, the compounds according to Preparation Examples I-2 Ba-1 and I-2 Bc-1 at an exemplary active ingredient concentration of 0.1% caused at least 98% to be killed after 7 days.
Beispiel B Example B
Test mit Boophilus microplus resistent / SP resistenter Parkhurst-Stamm Test with Boophilus microplus resistant / SP resistant Parkhurst strain
Testtiere: Adulte gesogene Weibchen Test animals: Adult suckled females
Lösungsmittel: Dimethylsulfoxid 20 mg Wirkstoff werden in 1 ml Dimethylsulfoxid gelöst, geringere Konzentrationen werden durch Verdünnen mit dem gleichen Lösungsmittel hergestellt. Solvent: Dimethyl sulfoxide 20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution with the same solvent.
Der Test wird in 5 -fach Bestimmung durchgeführt. 1 μl der Lösungen wird in das Abdomen injiziert, die Tiere in Schalen überfuhrt und in einem klimatisierten Raum aufbewahrt. Die Wirkungskontrolle erfolgt nach 7 Tagen auf Hemmung der Eiablage. Eine Wirkung von 100 % bedeutet, daß keine Zecke Eier gelegt hat. The test is carried out in 5-fold determination. 1 μl of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effectiveness check is carried out after 7 days on the inhibition of egg laying. An effect of 100% means that no tick has laid eggs.
In diesem Test zeigten z.B. die Verbindungen gemäß den Herstellungsbeispielen I-2 B-a-1, I-2 B-b-1 und I-2 B-c-1 bei einer beispielhaften Wirkstoffkonzentration von 20 μg/Tier eine Wirkung von 100 %.
In this test e.g. the compounds according to the preparation examples I-2 B-a-1, I-2 B-b-1 and I-2 B-c-1 with an exemplary active ingredient concentration of 20 μg / animal have an activity of 100%.
Claims
Patentansprüche Claims
Verbindungen der Formel (I) Compounds of formula (I)
in welcher für Halogen, Alkyl, Alkoxy, Alkylthio, Halogenalkyl, Halogenalkoxy, Nitro oder Cyano steht oder zwei Substituenten X gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gesättigten oder ungesättigten, gegebenenfalls substituierten Ring bilden, für 1, 2 oder 3 steht und für eine der Gruppen in which represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, nitro or cyano or two substituents X together with the carbon atoms to which they are attached form a saturated or unsaturated, optionally substituted ring for 1, 2 or 3 stands for one of the groups
(8) steht,
(8) stands,
worin für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Alkylthioalkyl, gegebenenfalls durch mindestens ein Heteroatom unterbrochenes gesättigtes oder ungesättigtes, gegebenenfalls substituiertes Cycloalkyl oder jeweils gegebenenfalls durch Halogen, Alkyl, Halogenalkyl, Alkoxy oder Nitro substituiertes Aryl, Arylalkyl oder Hetaryl steht, wherein hydrogen, in each case optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, optionally saturated or unsaturated, optionally substituted cycloalkyl interrupted by at least one heteroatom or in each case optionally substituted by halogen, alkyl, haloalkyl, alkoxy or nitro aryl, arylalkyl or hetaryl ,
B für Wasserstoff, Alkyl oder Alkoxyalkyl steht, oder B represents hydrogen, alkyl or alkoxyalkyl, or
A und B gemeinsam mit dem Kohlenstoffatom an das sie gebunden sind für einen gesättigten oder ungesättigten, gegebenenfalls durch mindestens ein Heteroatom unterbrochenen unsubstituierten oder substituierten Cyclus stehen, A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which is optionally interrupted by at least one heteroatom,
D für Wasserstoff oder gegebenenfalls substituierte Reste aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkylthioalkyl, gegebenenfalls durch mindestens ein Heteroatom unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Arylalkyl, Aryl, Hetarylalkyl oder Hetaryl steht oder D represents hydrogen or optionally substituted radicals from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, optionally saturated or unsaturated cycloalkyl, arylalkyl, aryl, hetarylalkyl or hetaryl interrupted by at least one heteroatom or
A und D gemeinsam mit den Atomen an die sie gebunden sind für einen gesättigten oder ungesättigten und gegebenenfalls durch mindestens ein Heteroatom unterbrochenen unsubstituierten oder substituierten Cyclus stehen, A and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally unsubstituted or substituted cycle interrupted by at least one heteroatom,
Q1, Q2, Q3 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertes Alkyl stehen oder
B und Q1 gemeinsam für eine gegebenenfalls substituierte Alkandiylgruppe stehen, Q 1 , Q 2 , Q 3 independently of one another represent hydrogen or optionally substituted alkyl or B and Q 1 together represent an optionally substituted alkanediyl group,
G für Wasserstoff (a) oder für eine der Gruppen G for hydrogen (a) or for one of the groups
steht, worin stands in what
E für ein Metallionäquivalent oder ein Ammoniumion steht, E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht, M für Sauerstoff oder Schwefel steht, L stands for oxygen or sulfur, M stands for oxygen or sulfur,
R1 für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Alkylthioalkyl, Polyalkoxyalkyl oder gegebenenfalls durch Halogen, Alkyl oder Alkoxy substituiertes Cycloalkyl, das durch mindestens ein Heteroatom unterbrochen sein kann, jeweils gegebenenfalls substituiertesR 1 for alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, which is optionally substituted by halogen, or cycloalkyl which is optionally substituted by halogen, alkyl or alkoxy and which can be interrupted by at least one heteroatom, in each case optionally substituted
Phenyl, Phenylalkyl, Hetaryl, Phenoxyalkyl oder Hetaryloxyalkyl steht, Phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2 für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkenyl, Alkoxyalkyl, Polyalkoxyalkyl oder für jeweils gegebenenfalls substituiertes Cycloalkyl, Phenyl oder Benzyl steht, R 2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, optionally substituted by halogen, or cycloalkyl, phenyl or benzyl, optionally substituted,
R3, R4 und R5 unabhängig voneinander für jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Alkoxy, Alkylamino, Dialkylamino, Alkylthio, Alkenylthio, Cycloalkylthio und für
jeweils gegebenenfalls substituiertes Phenyl, Phenylalkyl, Phenoxy oder Phenylthio stehen, R 3 , R 4 and R 5 independently of one another each represent optionally substituted by halogen alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and for each optionally substituted phenyl, phenylalkyl, phenoxy or phenylthio,
R6 und R7 unabhängig voneinander für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes Alkyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, für gegebenenfalls substituiertes Phenyl, für gegebenenfalls substituiertes Benzyl stehen, oder gemeinsam mit dem N-Atom, an das sie gebunden sind, für einen gegebenenfalls durch Sauerstoff oder Schwefel unterbrochenen Cyclus stehen. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher R 6 and R 7 independently of one another represent hydrogen, in each case optionally substituted by halogen substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, represent a cycle which may be interrupted by oxygen or sulfur. Compounds of formula (I) according to claim 1, in which
X für Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, C1-C6- Halogenalkyl, C1-C6-HalogenaIkoxy, Nitro oder Cyano steht oder zwei Substituenten X gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gesättigten oder ungesättigten, gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl, C1-C6-Halogenalkoxy, Nitro oder Cyano substituierten 5- bis 8-gliedrigen Carbocyclus bilden, n für 1, 2 oder 3 steht, X represents halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, nitro or cyano or two Substituents X together with the carbon atoms to which they are attached are saturated or unsaturated, optionally by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C Form 6 -haloalkoxy, nitro or cyano substituted 5- to 8-membered carbocycle, n represents 1, 2 or 3,
Z für eine der Gruppen Z for one of the groups
(8) steht,(8) stands,
A für Wasserstoff oder jeweils gegebenenfalls durch Halogen substituiertes C1-C12-Alkyl, C2-C8-Alkenyl, C1-C10-Alkoxy-C1-C8-alkyl, Poly-C1-C8-alkoxy-C1-C8-alkyl, C1-C10-Alkylthio-C1-C6-alkyl, gegebenenfalls durch C1-C6-Alkyl, Halogen oder C1-C8-Alkoxy substituiertes Cycloalkyl mit 3 bis 8 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, oder für jeweils gegebenenfalls durch Halogen, C1-C6- Alkyl, C1-C6-Halogenalkyl, C1-C6- Alkoxy oder Nitro substituiertes C6- oder C10-Aryl, Hetaryl mit 5 bis 6 Ringatomen und ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel oder C6- oder C10-Aryl-C1-C6- alkyl steht, A for hydrogen or in each case optionally substituted by halogen C 1 -C 12 alkyl, C 2 -C 8 alkenyl, C 1 -C 10 alkoxy-C 1 -C 8 alkyl, poly-C 1 -C 8 alkoxy -C 1 -C 8 alkyl, C 1 -C 10 alkylthio-C 1 -C 6 alkyl, optionally substituted by C 1 -C 6 alkyl, halogen or C 1 -C 8 alkoxy cycloalkyl having 3 to 8 Ring atoms, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, or in each case optionally by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or nitro-substituted C 6 - or C 10 -aryl, hetaryl with 5 to 6 ring atoms and one to three heteroatoms from the series nitrogen, oxygen and sulfur or C 6 - or C 10 -aryl-C 1 -C 6 -alkyl,
B für Wasserstoff, C1-C12-Alkyl oder C1-C8-Alkoxy-C1-C8-alkyl steht oder B represents hydrogen, C 1 -C 12 alkyl or C 1 -C 8 alkoxy-C 1 -C 8 alkyl or
A, B und das Kohlenstoffatom an das sie gebunden sind, für einen gesättigten oder ungesättigten C3-C10-Spirocyclus stehen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und der gegebenenfalls durch C1-C8-Alkyl, C3-C10-Cycloalkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy, C1-C8-Alkylthio, Halogen oder Phenyl substituiert ist oder
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C6-Spirocyclus stehen, der durch eine gegebenenfalls durch ein oder zwei Sauerstoff- und/oder Schwefelatome unterbrochenen Alkylendiyl-, oder durch einen Alkylendioxyl- oder durch eine Alkylendithioyl-Gruppe substituiert ist, die mit dem Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis achtgliedrigen Spirocyclus bildet oder A, B and the carbon atom to which they are attached represent a saturated or unsaturated C 3 -C 10 spirocycle, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C 1 - C 8 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, halogen or phenyl or is substituted A, B and the carbon atom to which they are attached represent a C 3 -C 6 spirocycle, which is interrupted by an alkylene diyl, or by an alkylenedioxyl or by an, optionally interrupted by one or two oxygen and / or sulfur atoms Alkylenedithioyl group is substituted, which forms a further five to eight-membered spirocycle with the carbon atom to which it is attached or
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C8-Spirocyclus stehen, bei dem zwei Substituenten gemeinsam für einen gegebenenfalls durch C1-C6-Alkyl, C1-C6-Alkoxy oder Halogen substituierten gesättigten oder einfach oder mehrfach ungesättigten 5- bis 8-gliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoff- oder Schwefel atom enthält, A, B and the carbon atom to which they are attached represent a C 3 -C 8 -spirocycle, in which two substituents together for one optionally by C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen substituted saturated or mono- or polyunsaturated 5- to 8-membered cycle which optionally contains an oxygen or sulfur atom,
D für Wasserstoff, jeweils gegebenenfalls durch Halogen substituiertes C1-C1-rAlkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, C1-C10-Alkoxy-C2-C8- alkyl, Poly-C1-C8-alkoxy-C2-C8-alkyl, C1-C10-Alkylthio-C2-C8-alkyl, gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Alkoxy oder C1- C4-Halogenalkyl substituiertes Cycloalkyl mit 3 bis 8 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylenngruppen durch Sauerstoff und/oder Schwefel ersetzt sind oder jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C8- Halogenalkyl, C1-C6-Alkoxy oder Nitro substituiertes Phenyl, Hetaryl mit 5 bis 6 Ringatomen und ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel oder Phenyl-C1-C6-alkyl steht oder D for hydrogen, in each case optionally substituted by halogen C 1 -C 1 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 10 alkoxy-C 2 -C 8 alkyl, poly -C 1 -C 8 alkoxy-C 2 -C 8 alkyl, C 1 -C 10 alkylthio-C 2 -C 8 alkyl, optionally by halogen, C 1 -C 4 alkyl, C 1 -C 4 -Alkoxy or C 1 - C 4 -haloalkyl-substituted cycloalkyl having 3 to 8 ring atoms, in which one or two non-directly adjacent methyl groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 6 -alkyl, C 1 -C 8 - haloalkyl, C 1 -C 6 alkoxy or nitro substituted phenyl, hetaryl with 5 to 6 ring atoms and one to three heteroatoms from the series nitrogen, oxygen and sulfur or phenyl-C 1 -C 6 alkyl or
A und D gemeinsam mit den Atomen, an die sie gebunden sind, für eine gegebenenfalls einfach bis vierfach, gleich oder verschieden substituierte Alkandiyl- oder Alkendiylgruppierung mit 3 bis 6 Kohlenstoffatomen stehen, A and D together with the atoms to which they are attached represent an alkanediyl or alkenediyl group with 3 to 6 carbon atoms which may be monosubstituted to tetrasubstituted in the same way or differently,
worin a) gegebenenfalls eine oder zwei nicht direkt benachbarte where a) optionally one or two not directly adjacent
Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und wobei als Substituenten in Frage kommen
Halogen, Hydroxy, Mercapto oder jeweils gegebenenfalls durch Halogen substituiertes C1-C10-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, C3-C7-Cycloalkyl, Phenyl oder Benzyloxy; Methylene groups are replaced by oxygen and / or sulfur and are suitable as substituents Halogen, hydroxy, mercapto or in each case optionally substituted by halogen C 1 -C 10 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 3 -C 7 cycloalkyl, phenyl or benzyloxy;
oder eine weitere Alkandiylgruppierung mit 3 bis 6 Kohlenstoffatomen, die gegebenenfalls durch C1-C6-Alkyl substituiert ist oder in der gegebenenfalls zwei benachbarte Substituenten mit den Kohlenstoffatomen, an die sie gebunden sind, einen weiteren gesättigten oder ungesättigten C5-C6-Cyclus bilden; or a further alkanediyl grouping with 3 to 6 carbon atoms, which is optionally substituted by C 1 -C 6 -alkyl or in which two adjacent substituents with the carbon atoms to which they are attached optionally contain a further saturated or unsaturated C 5 -C 6 - Form cycle;
oder die b) gegebenenfalls durch eine der nachfolgenden Gruppierungen or b) optionally by one of the following groupings
unterbrochen ist, is interrupted
Q1 , Q2, Q3 unabhängig voneinander für Wasserstoff oder gegebenenfalls durch Halogen substituiertes C1-C6-Alkyl stehen oder B und Q1 gemeinsam für eine C1-C6-Alkandiylgruppierung stehen, die gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiert ist,
G für Wasserstoff (a) oder für eine der Gruppen Q 1 , Q 2 , Q 3 independently of one another represent hydrogen or C 1 -C 6 -alkyl optionally substituted by halogen or B and Q 1 together represent a C 1 -C 6 -alkanediyl group which may be replaced by halogen or C 1 - C 6 alkyl is substituted, G for hydrogen (a) or for one of the groups
E (f) oder (g) steht,E (f) or (g) stands,
in welchen in which
E für ein Metallionäquivalent oder ein Ammoniumion steht, L für Sauerstoff oder Schwefel steht und E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and
M für Sauerstoff oder Schwefel steht, R1 für jeweils gegebenenfalls durch Halogen substituiertes C1-C20-Alkyl, C2-C20-Alkenyl, C1-C8-Alkoxy-C1-C8-alkyl, C1-C8-Alkylthio- C1-C8-alkyl, Poly-C1-C8-alkoxy-C1-C8-alkyl oder gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes Cycloalkyl mit 3 bisM represents oxygen or sulfur, R 1 represents in each case optionally substituted by halogen C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 1 - C 8 -alkylthio- C 1 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or cycloalkyl optionally substituted by halogen or C 1 -C 6 -alkyl with 3 to
8 Ringatomen, in welchem gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, für gegebenenfalls durch Halogen, Nitro, C1-C6-Alkyl, C1-C6- Alkoxy, C1-C6-Halogenalkyl, C1-C6-Halogenalkoxy, C1-C6-Alkylthio oder C1-C8-Alkylsulfonyl substituiertes Phenyl, für gegebenenfalls durch Halogen, C1-C8-Alkyl, C1-C6-Alkoxy, C1- C6-Halogenalkyl oder C1-C6-Halogenalkoxy substituiertes Phenyl- C1-C6-alkyl. für gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes 5- oder 6-gliedriges Hetaryl mit ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel,
für gegebenenfalls durch Halogen oder C1-C6-Alkyl substituiertes Phenoxy-C1-C6-alkyl oder für gegebenenfalls durch Halogen, Amino oder C1-C6-Alkyl substituiertes 5- oder 6-gliedriges Hetaryloxy-C1-C6-alkyl mit ein bis drei Heteroatomen aus der Reihe Stickstoff, Sauerstoff und Schwefel steht, 8 ring atoms, in which one or two not directly adjacent methylene groups are replaced by oxygen and / or sulfur, optionally by halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 -Halogenalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio or C 1 -C 8 -alkylsulfonyl-substituted phenyl, for optionally substituted by halogen, C 1 -C 8 -alkyl, C 1 -C 6 -alkoxy, C 1 - C 6 haloalkyl or C 1 -C 6 -haloalkoxy-substituted phenyl C 1 -C 6 alkyl. for 5- or 6-membered hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl and having one to three heteroatoms from the series nitrogen, oxygen and sulfur, for phenoxy-C 1 -C 6 -alkyl optionally substituted by halogen or C 1 -C 6 -alkyl or for 5- or 6-membered hetaryloxy-C 1 -C -substituted optionally substituted by halogen, amino or C 1 -C 6 -alkyl 6 -alkyl with one to three heteroatoms from the series nitrogen, oxygen and sulfur,
R2 für jeweils gegebenenfalls durch Halogen substituiertes C1-C20-Alkyl, C3-C20-Alkenyl, C1-C8-Alkoxy-C1-C8-alkyl oder Poly-C1-C8- alkoxy-C1-C8-alkyl, für gegebenenfalls durch Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes C3-C8-Cycloalkyl, oder für jeweils gegebenenfalls durch Halogen, Nitro, C1-C8-Alkyl, C1- C6-Alkoxy oder C1-C6-Halogenalkyl substituiertes Phenyl oder Benzyl steht, R3 für gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl oder für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C3-Halogenalkyl, C1-C3-Halogenalkoxy, Nitro oder Cyano substituiertes Benzyl oder Phenyl steht, R 2 is in each case optionally substituted by halogen C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or poly-C 1 -C 8 alkoxy- C 1 -C 8 alkyl, for C 3 -C 8 cycloalkyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, or for each optionally substituted by halogen, nitro, C 1 -C 8 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkyl substituted phenyl or benzyl, R 3 represents optionally substituted by halogen C 1 -C 8 alkyl or for each optionally substituted by halogen, C 1 -C 6- alkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy, nitro or cyano-substituted benzyl or phenyl,
R4 und R5 unabhängig voneinander für gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl, C1-C8-Alkoxy, C1-C8-Alkylamino, Di-(C1- C8-alkyl)-amino, C1-C8-Alkylthio, C2-C8-Alkenylthio, C3-C7-Cycloalkylthio oder für jeweils gegebenenfalls durch Halogen, Nitro, Cyano, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1- C4-Halogenalkylthio, C1-C4-Alkyl oder C1-C4-Halogenalkyl substituiertes Phenyl, Phenoxy oder Phenylthio stehen, R 4 and R 5 independently of one another are optionally substituted by halogen-substituted C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylamino, di- (C 1 -C 8 alkyl) amino, C 1 -C 8 alkylthio, C 2 -C 8 alkenylthio, C 3 -C 7 cycloalkylthio or for each optionally halogen, nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 - C 4 haloalkylthio, C 1 -C 4 alkyl or C 1 -C 4 -halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
R6 und R7 unabhängig voneinander für Wasserstoff, für jeweils gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl, C3-C8-Cycloalkyl, C1-C8-Alkoxy, C3-C8-Alkenyl, C1-C8-Alkoxy-C1-C8-alkyl, für gegebenenfalls durch Halogen, C1-C8-Halogenalkyl, C1-C8-Alkyl oder C1-C8-Alkoxy substituiertes Phenyl, gegebenenfalls durch
Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl oder C1-C8-Alkoxy substituiertes Benzyl oder zusammen für C3-C6-Alkandiyl stehen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, R13 für Wasserstoff, für jeweils gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl, C1-C8-Alkoxy oder C3-C8-Cycloalkyl oder für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C3-Halogenalkyl, C1-C3-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl steht, R14 und R15 unabhängig voneinander für Wasserstoff, C1-C8-Alkyl, C1-C8- Halogenalkyl, C3-C6-CycIoalkyl, für jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C3-Halogenalkyl, C1-C3- Halogenalkoxy, Cyano oder Nitro substituiertes Phenyl oder Benzyl oder gemeinsam für eine gegebenenfalls durch C1-C4-Alkyl substituierte C4-C6-Alkandiylgruppe stehen, R 6 and R 7 independently of one another for hydrogen, for in each case optionally substituted by halogen C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, for optionally substituted by halogen, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, optionally by Halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl or C 1 -C 8 alkoxy substituted benzyl or together represent C 3 -C 6 alkanediyl, in which a methylene group is optionally replaced by oxygen or sulfur, R 13 for hydrogen, for each optionally substituted by halogen C 1 -C 8 alkyl, C 1 -C 8 alkoxy or C 3 -C 8 cycloalkyl or for each optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro or cyano substituted phenyl or benzyl, R 14 and R 15 independently of one another represent hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 6 cycloalkyl, for each optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 - haloalkoxy, cyano or nitro-substituted phenyl or benzyl or together represent a C 4 -C 6 -alkanediyl group which is optionally substituted by C 1 -C 4 -alkyl,
R16 und R17 gleich oder verschieden sind und für C1-C8-Alkyl stehen oder R 16 and R 17 are the same or different and are C 1 -C 8 alkyl or
R16 und R17 gemeinsam für einen C2-C4-Alkandiylrest stehen, der gegebenenfalls durch C1-C6-Alkyl oder durch gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl substituiert ist, R 16 and R 17 together represent a C 2 -C 4 alkanediyl radical, which may be optionally by C 1 -C 6 alkyl or by optionally halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl,
R18 und R19 unabhängig voneinander für Wasserstoff, gegebenenfalls durch Halogen substituiertes C1-C8-Alkyl oder gegebenenfalls durch Halogen, C1-C8-Alkyl, C1-C8-Alkoxy, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl stehen und R20 und R21 unabhängig voneinander für C1-C10-Alkyl, C3-C10-Alkenyl, C1-C10-Alkoxy, C1-C10-Alkylamino, C3-C10-Alkenylamino, Di-(C1- C10-alkyl)-amino oder Di-(C3-C10-alkenyl)-amino stehen. R 18 and R 19 independently of one another for hydrogen, optionally substituted by halogen C 1 -C 8 alkyl or optionally by halogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro or cyano substituted phenyl and R 20 and R 21 independently of one another are C 1 -C 10 alkyl, C 3 -C 10 alkenyl, C 1 -C 10 alkoxy, C 1 - are amino or di- (C 3 -C 10 -alkenyl) -amino - C 10 alkylamino, C 3 -C 10 -alkenylamino, di- (C 10 alkyl C 1).
3. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher
X für Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy, Nitro oder Cyano steht, 3. Compounds of formula (I) according to claim 1, in which X represents fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro or Cyano stands
oder zwei Substituenten X gemeinsam mit den Kohlenstoff atomen, an die sie gebunden sind, einen gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy, Nitro oder Cyano substituierten ungesättigten 5- bis 7- gliedrigen Carbocyclus bilden, n für 1, 2 oder 3 steht, Z für eine der Gruppen or two substituents X together with the carbon atoms to which they are attached, one optionally by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C Form 1 -C 4 haloalkoxy, nitro or cyano substituted unsaturated 5- to 7-membered carbocycle, n represents 1, 2 or 3, Z represents one of the groups
(8) steht,(8) stands,
A für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C10-Alkyl, C2-C6-Alkenyl, C1-C8-Alkoxy-C1-C6-alkyl, Poly-C1-C6-alkoxy-C1-C6-alkyl, C1-C8-Alkylthio-C1-C6-alkyl, gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkoxy, Fluor oder Chlor substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind, oder jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder Nitro substituiertes Phenyl, Furanyl, Pyridyl, Imidazolyl, Triazolyl, Pyrazolyl, Indolyl, Thiazolyl, Thienyl oder A for hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 10 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, poly-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 8 -alkylthio-C 1 -C 6 -alkyl, cycloalkyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine or chlorine with 3 to 7 ring atoms, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, or in each case optionally by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or nitro substituted phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or
Phenyl-C1-C4-alkyl steht, Phenyl-C 1 -C 4 -alkyl,
B für Wasserstoff, C1-C10-Alkyl oder C1-C6-Alkoxy-C1-C4-alkyl steht oder B represents hydrogen, C 1 -C 10 alkyl or C 1 -C 6 alkoxy-C 1 -C 4 alkyl or
A, B und das Kohlenstoffatom an das sie gebunden sind, für einen gesättigten oder ungesättigten C3-C9-Spirocyclus stehen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind und der gegebenenfalls durch C1-C6-Alkyl, C3-C8-Cycloalkyl, C1-C3-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, Fluor, Chlor oder Phenyl substituiert ist oder A, B and the carbon atom to which they are attached represent a saturated or unsaturated C 3 -C 9 spirocycle, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur and which is optionally replaced by C 1 - C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, fluorine, chlorine or phenyl or is substituted
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C6-Spirocyclus stehen, der durch eine gegebenenfalls durch ein oder zwei Sauerstoff- oder Schwefelatome unterbrochenen Alkylendiyl- oder durch eine Alkylendioxyl- oder durch eine Alkylendithiol- Gruppe substituiert ist, die mit dem Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis siebengliedrigen Spirocyclus bildet oder A, B and the carbon atom to which they are attached represent a C 3 -C 6 spirocycle, which is interrupted by an alkylenediyl group, optionally interrupted by one or two oxygen or sulfur atoms, or by an alkylenedioxyl or by an alkylenedithiol group is substituted, which forms a further five- to seven-membered spirocycle with the carbon atom to which it is attached or
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C6-Spirocyclus stehen, bei dem zwei Substituenten gemeinsam für einen gegebenenfalls durch C1-C5-Alkyl, C1-C5-Alkoxy, Fluor,A, B and the carbon atom to which they are attached represent a C 3 -C 6 spirocycle, in which two substituents together for one optionally by C 1 -C 5 alkyl, C 1 -C 5 alkoxy, fluorine ,
Chlor oder Brom substituierten gesättigten oder einfach oder mehrfach ungesättigten 5- oder 6-gliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoff- oder Schwefelatom enthält,
D für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C10-Alkyl, C3-C6-AIkenyl, C3-C6-Alkinyl, C1-C8- Alkoxy-C2-C6-alkyl, Poly-C1-C6-alkoxy-C2-C6-alkyl, C1-C8-Alkylthio-C2-C6-alkyl, gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkoxy oder C1-C2-Halogenalkyl substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind oder jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1- C4-Halogenalkyl, C1-C4-Alkoxy oder Nitro substituiertes Phenyl, Pyridyl, Thienyl, Furanyl, Thiazolyl, Pyrimidyl, Pyrazolyl oderChlorine or bromine substituted saturated or mono- or polyunsaturated 5- or 6-membered cycle, which optionally contains an oxygen or sulfur atom, D for hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 10 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 8 -alkoxy-C 2 -C 6 -alkyl , Poly-C 1 -C 6 alkoxy-C 2 -C 6 alkyl, C 1 -C 8 alkylthio-C 2 -C 6 alkyl, optionally by C 1 -C 4 alkyl, C 1 -C 4 -Alkoxy or C 1 -C 2 haloalkyl-substituted cycloalkyl having 3 to 7 ring atoms, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 4 alkyl, C 1 - C 4 haloalkyl, C 1 -C 4 alkoxy or nitro substituted phenyl, pyridyl, thienyl, furanyl, thiazolyl, pyrimidyl, pyrazolyl or
Phenyl-C1-C4-alkyl steht oder Phenyl-C 1 -C 4 alkyl is or
A und D gemeinsam mit den Atomen, an die sie gebunden sind, für eine C3-C5-Alkandiyl- oder C3-C5-Alkendiylgruppierung stehen, worin a) gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist und welche gegebenenfalls durch Fluor, Chlor,A and D together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl group, in which a) a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by Fluorine, chlorine,
Hydroxy, Mercapto oder durch jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C6-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C3-C6-Cycloalkyl, Phenyl oder Benzyl substituiert ist; Hydroxy, mercapto or by C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 3 -C 6 cycloalkyl, phenyl or benzyl, each substituted by fluorine or chlorine;
oder die b) gegebenenfalls durch eine der nachfolgenden Gruppierungen or b) optionally by one of the following groupings
;;
oderor
unterbrochen ist; oder worin A und D im Fall von Verbindungen der Formel (I-1) gemeinsam mit den Atomen, an die sie gebunden sind, für eine der Gruppen AD-1 bis AD-20 steht
is interrupted; or in which, in the case of compounds of the formula (I-1), A and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-20
Q1, Q2, Q3 unabhängig voneinander für Wasserstoff oder gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl stehen oder Q 1 , Q 2 , Q 3 independently of one another represent hydrogen or C 1 -C 4 -alkyl optionally substituted by fluorine or chlorine or
B und Q1 für eine C1-C4-Alkandiylgruppierung stehen, die gegebenenfalls durch Fluor, Chlor oder C1-C4-Alkyl substituiert ist, G für Wasserstoff (a) oder für eine der Gruppen B and Q 1 represent a C 1 -C 4 alkanediyl group which is optionally substituted by fluorine, chlorine or C 1 -C 4 alkyl, G represents hydrogen (a) or one of the groups
in welchen in which
E für ein Metallionaquivalent oder ein Ammoniumion steht, E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht und M für Sauerstoff oder Schwefel steht, L stands for oxygen or sulfur and M stands for oxygen or sulfur,
R1 für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1- C16-Alkyl, C2-C16-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkylthio-C1-C6-alkyl, Poly-C1-C6-alkoxy-C1-C6-alkyl oder gegebenenfalls durch Fluor, Chlor oder C1-C5-Alkyl substituiertes Cycloalkyl mit 3 bis 7 Ringatomen, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind,
für gegebenenfalls durch Fluor, Chlor, Brom, Nitro, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C3-Halogenalkyl, C1-C3-Halogenalkoxy, C1-C4- Alkylthio oder C1-C4-Alkylsulfonyl substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4- Alkoxy, C1-C3-Halogenalkyl oder C1-C3-Halogenalkoxy substituiertes Phenyl-C1-C4-alkyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom oder C1-C4- Alkyl substituiertes Pyrazolyl, Thiazolyl, Pyridyl, Pyrimidyl, Furanyl oder Thienyl, für gegebenenfalls durch Fluor, Chlor, Brom oder C1-C4-Alkyl substituiertes Phenoxy-C1-C5-alkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Amino oder C1-C4-Alkyl substituiertes Pyridyloxy-C1-C5-alkyl, Pyrimidyloxy- C1-C5-alkyl oder Thiazolyloxy-C1-C5-alkyl, R2 für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1- C16-Alkyl, C3-C16-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl oder Poly- C1-C6-alkoxy-C1-C8-alkyl, für gegebenenfalls durch Fluor, Chlor, C1-C3-Alkyl oder C1-C3- Alkoxy substituiertes C3-C7-Cycloalkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, C1-C4- Alkyl, C1-C3-Alkoxy oder C1-C3-Halogenalkyl substituiertes Phenyl oder Benzyl steht, R 1 represents in each case optionally substituted by fluorine or chlorine, C 1 - C 16 alkyl, C 2 -C 16 alkenyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 -alkylthio C 1 -C 6 alkyl, poly-C 1 -C 6 alkoxy-C 1 -C 6 alkyl or cycloalkyl with 3 to 7 ring atoms optionally substituted by fluorine, chlorine or C 1 -C 5 alkyl, where optionally one or two methylene groups which are not directly adjacent are replaced by oxygen and / or sulfur, for optionally by fluorine, chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl substituted phenyl, for optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkyl or C 1 -C 3 - Halogenalkoxy-substituted phenyl-C 1 -C 4 -alkyl, for pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl, for optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 alkyl-substituted phenoxy-C 1 -C 5 -alkyl or for pyridyloxy-C 1 -C 5 -alkyl, pyrimidyloxy which are each optionally substituted by fluorine, chlorine, bromine, amino or C 1 -C 4 -alkyl - C 1 -C 5 -alkyl or thiazolyloxy-C 1 -C 5 alkyl, R 2 represents in each case optionally substituted by fluorine or chlorine, C 1 - C 16 alkyl, C 3 -C 16 alkenyl, C 1 -C 6 -Alkoxy-C 1 -C 6 -alkyl or poly-C 1 -C 6 -a lkoxy-C 1 -C 8 alkyl, for C 3 -C 7 cycloalkyl optionally substituted by fluorine, chlorine, C 1 -C 3 alkyl or C 1 -C 3 alkoxy or for each optionally substituted by fluorine, chlorine, bromine , Nitro, C 1 -C 4 alkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkyl substituted phenyl or benzyl,
R3 für gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1- C4-Alkyl, C1-C4-Alkoxy, C1-C2-Halogenalkyl, C1-C2-Halogenalkoxy, Nitro oder Cyano substituiertes Benzyl oder Phenyl steht, R 3 is optionally substituted by fluorine or chlorine, C 1 -C 8 alkyl or optionally substituted by fluorine, chlorine, bromine, C 1 respectively - C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 -haloalkyl C 1 -C 2 haloalkoxy, nitro or cyano substituted benzyl or phenyl,
R4 und R3 unabhängig voneinander für jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkyl-
amino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylthio, C3-C4-Alkenylthio, C3-C6-Cycloalkylthio oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, Cyano, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, C1-C3-Alkylthio, C1-C3-Halogenalkylthio, C1-C3-Alkyl oder C1-C3- Halogenalkyl substituiertes Phenyl, Phenoxy oder Phenylthio stehen, R 4 and R 3 independently of one another each represent C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl which are optionally substituted by halogen amino, di- (C 1 -C 6 alkyl) amino, C 1 -C 6 alkylthio, C 3 -C 4 alkenylthio, C 3 -C 6 cycloalkylthio or for each optionally by fluorine, chlorine, bromine, Nitro, cyano, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkyl or C 1 -C 3 - Haloalkyl substituted phenyl, phenoxy or phenylthio,
R6 und R7 unabhängig voneinander für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C8-Alkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C3-C6- Alkenyl, C1-C6-Alkoxy-C1- C6-alkyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C5-Halogenalkyl, C1-C5-Alkyl oder C1-Cj-Alkoxy substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C5-Alkyl, C1-C5-Halogenalkyl oder C1-C5-Alkoxy substituiertes Benzyl, oder zusammen für C3-C6-Alkandiyl stehen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, R13 für Wasserstoff, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl, C1-C6-Alkoxy oder C3-C7-Cycloalkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1-C4- Alkyl, C1-C4-Alkoxy, C1-C2-Halogenalkyl, C1-C2-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl steht, R14 und R15 unabhängig voneinander für Wasserstoff, C1-C6-Alkyl, C1-C6- Halogenalkyl, C3-C6-Cycloalkyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C2-Halogenalkyl, C1-C2-Halogenalkoxy, Cyano oder Nitro substituiertes Phenyl oder Benzyl oder gemeinsam für eine gegebenenfalls durch C1-C3- Alkyl substituierte C4-C5-Alkandiylgruppe stehen, R 6 and R 7 independently of one another for hydrogen, for in each case optionally substituted by fluorine, chlorine or bromine, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 - Alkenyl, C 1 -C 6 alkoxy-C 1 - C 6 alkyl, for optionally by fluorine, chlorine, bromine, C 1 -C 5 haloalkyl, C 1 -C 5 alkyl or C 1 -C j alkoxy substituted phenyl, optionally substituted by fluorine, chlorine, bromine, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy, or together represent C 3 -C 6 alkanediyl, wherein optionally a methylene group is replaced by oxygen or sulfur, R 13 for hydrogen, for each optionally substituted by fluorine or chlorine substituted C 1 -C 8 alkyl, C 1 -C 6 alkoxy or C 3 -C 7 cycloalkyl or for each phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, nitro or cyano, R 14 and R 15 una epending one another represent hydrogen, C 1 -C 6 alkyl, C 1 -C 6 - haloalkyl, C 3 -C 6 cycloalkyl, in each case optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 - C 4 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, cyano or nitro substituted phenyl or benzyl or together represent a C 4 -C 5 alkanediyl group which is optionally substituted by C 1 -C 3 alkyl ,
R16 und R17 gleich oder verschieden sind und für C1-C4-Alkyl stehen oder R 16 and R 17 are the same or different and are C 1 -C 4 alkyl or
R16 und R17 zusammen für einen C2-C3-Alkandiylrest stehen, der gegebenenfalls durch C1-C4-Alkyl oder durch gegebenenfalls durch C1- C2-Alkyl, C1-C2-Halogenalkyl, C1-C2-Alkoxy, C1-C2-Halogenalkoxy, Nitro oder Cyano substituiertes Phenyl substituiert ist. R 16 and R 17 alkanediyl 3 together represent a C 2 -C, optionally substituted by C 1 -C 4 alkyl or by optionally substituted by C 1 - C 2 alkyl, C 1 -C 2 haloalkyl, C 1 - C 2 alkoxy, C 1 -C 2 haloalkoxy, nitro or cyano substituted phenyl.
4. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher
X für Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso-Propyl, Butyl, iso-Butyl, tert.-Butyl, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano steht 4. Compounds of formula (I) according to claim 1, in which X represents fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, trifluoromethyl, trifluoromethoxy, nitro or cyano
oder zwei Substituenten X gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Methoxy, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano substituierten, ungesättigten 6-gliedrigen Carbocyclus bilden, n für 1, 2 oder 3 steht, Z für eine der Gruppen or two substituents X together with the carbon atoms to which they are attached form an unsaturated 6-membered carbocycle optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, n for 1, 2 or 3 stands for Z for one of the groups
steht,stands,
A für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl, C2-C4-Alkenyl, C1-C6-Alkoxy-C1-C4- alkyl, Poly-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-Alkylthio-C1-C4-alkyl,
Cycloalkyl mit 3 bis 6 Ringatomen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso-Propyl, Methoxy, Ethoxy, Trifluormethyl oder Nitro substituiertes Phenyl, Furanyl, Pyridyl, Imidazolyl, Pyrazolyl,A for hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, poly-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl, Cycloalkyl with 3 to 6 ring atoms, in which a methylene group is optionally replaced by oxygen or sulfur, or for phenyl, furanyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or nitro , Pyridyl, imidazolyl, pyrazolyl,
Triazolyl, Indolyl, Thiazolyl, Thienyl oder Benzyl steht, Triazolyl, indolyl, thiazolyl, thienyl or benzyl,
B für Wasserstoff, C1-C8-Alkyl oder C1-C4-Alkoxy-C1-C2-alkyl steht oder B represents hydrogen, C 1 -C 8 alkyl or C 1 -C 4 alkoxy-C 1 -C 2 alkyl or
A, B und das Kohlenstoffatom an das sie gebunden sind, für einen gesättigten oder ungesättigten C3-C8-Spirocyclus stehen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, und der gegebenenfalls einfach oder mehrfach durch Methyl, Ethyl, Propyl, Isopropyl, Butyl, iso-Butyl, sec.-Butyl, tert,- Butyl, Cyclohexyl, Trifluormethyl, Methoxy, Ethoxy, Propoxy, iso- Propoxy, Butoxy, iso-Butoxy, sek.-Butoxy, tert.-Butoxy, Methylthio,A, B and the carbon atom to which they are attached represent a saturated or unsaturated C 3 -C 8 -spirocycle, in which a methylene group is optionally replaced by oxygen or sulfur, and which is optionally mono- or polysubstituted by methyl, ethyl, propyl, Isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, propoxy, iso-propoxy, butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio,
Ethylthio, Fluor, Chlor oder Phenyl substituiert ist oder Ethylthio, fluorine, chlorine or phenyl is substituted or
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C6-Spirocyclus stehen, der durch eine gegebenenfalls durch einA, B and the carbon atom to which they are attached represent a C 3 -C 6 spirocycle, which may be replaced by a
Sauerstoff- oder Schwefelatom unterbrochene Alkylendiyl- oder durch eine Alkylendioxyl-Gruppe substituiert ist, die mit demOxygen or sulfur atom interrupted alkylenediyl or substituted by an alkylenedioxyl group which with the
Kohlenstoffatom, an das sie gebunden ist, einen weiteren fünf- bis siebengliedrigen Spirocyclus bildet oder Carbon atom to which it is attached forms a further five- to seven-membered spirocycle or
A, B und das Kohlenstoffatom, an das sie gebunden sind, für einen C3- C6-Spirocyclus stehen, bei dem zwei Substituenten gemeinsam für einen gesättigten oder einfach bis dreifach ungesättigten fünf- oder sechsgliedrigen Cyclus stehen, der gegebenenfalls ein Sauerstoffoder Schwefelatom enthält, A, B and the carbon atom to which they are attached represent a C 3 - C 6 spirocycle, in which two substituents together represent a saturated or mono- to tri-unsaturated five- or six-membered cycle which optionally contains an oxygen or sulfur atom ,
D für Wasserstoff, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C8-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, C1-C6- Alkoxy-C2-C4-alkyl, Poly-C1-C4-alkoxy-C2-C4-alkyl, C1-C4-Alkylthio-C2-C4-alkyl, C3-C6-Cycloalkyl, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist, oder
jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, iso-Propyl, Methoxy, Ethoxy, Trifluormethyl oder Nitro substituiertes Phenyl, Benzyl, Pyridyl, Thienyl, Furanyl oder Thiazolyl steht, oder D for hydrogen, in each case optionally substituted by fluorine or chlorine, C 1 -C 8 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 6 -alkoxy-C 2 -C 4 -alkyl , Poly-C 1 -C 4 alkoxy-C 2 -C 4 alkyl, C 1 -C 4 alkylthio-C 2 -C 4 alkyl, C 3 -C 6 cycloalkyl, where optionally a methylene group by oxygen or Sulfur is replaced, or each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or nitro, phenyl, benzyl, pyridyl, thienyl, furanyl or thiazolyl, or
A und D gemeinsam mit den Atomen, an die sie gebunden sind für eine C3-C5-Alkandiyl- oder C3-C5-Alkendiylgruppierung stehen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist und welche gegebenenfalls durch Fluor, Chlor, Hydroxy, Mercapto oder durch jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C6-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C3-C6- Cycloalkyl, Phenyl oder Benzyloxy substituiert ist, oder, im Falle von Verbindungen der Formel (I-1), für eine der folgenden Gruppierungen A and D together with the atoms to which they are attached represent a C 3 -C 5 -alkanediyl or C 3 -C 5 -alkenediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by fluorine, chlorine , Hydroxy, Mercapto or by in each case optionally substituted by fluorine or chlorine substituted by C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 3 -C 6 - cycloalkyl, phenyl or benzyloxy , or, in the case of compounds of the formula (I-1), for one of the following groupings
Q1, Q2, Q3 unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen oder Q 1 , Q 2 , Q 3 independently of one another represent hydrogen, methyl or ethyl or
B und Q1 gemeinsam für eine C1-C4-Alkandiylgruppierung stehen, die gegebenenfalls durch Fluor, Chlor, Methyl oder Ethyl substituiert ist, B and Q 1 together represent a C 1 -C 4 -alkanediyl group which is optionally substituted by fluorine, chlorine, methyl or ethyl,
G für Wasserstoff (a) oder für eine der Gruppen G for hydrogen (a) or for one of the groups
E (f) oder (g) steht,E (f) or (g) stands,
in welchen E für ein Metallionäquivalent oder ein Ammoniumion steht, in which E represents a metal ion equivalent or an ammonium ion,
L für Sauerstoff oder Schwefel steht und L represents oxygen or sulfur and
M für Sauerstoff oder Schwefel steht, M represents oxygen or sulfur,
R1 für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1- C14-Alkyl, C2-C14-Alkenyl, C1-C4-Alkoxy-C1-C6-alkyl, C1-C4-Alkylthio-C1-C6-alkyl, Poly-C1-C4-alkoxy-C1-C4-alkyl oder gegebenenfalls durch Fluor, Chlor, Methyl, Ethyl, Propyl, i-Propyl, Butyl, i-Butyl oder tert.-Butyl substituiertes C3-C6-Cycloalkyl, worin gegebenenfalls eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff und/oder Schwefel ersetzt sind,
für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, i-Propyl, Methoxy, Ethoxy, Trifluormethyl, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfonyl, Ethylsulfonyl oder Nitro substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Propyl, i-Propyl, Methoxy, Ethoxy, Trifluormethyl oder Trifluormethoxy substituiertes Benzyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Furanyl, Thienyl, Pyridyl, Pyrimidyl, Thiazolyl oder Pyrazolyl, für gegebenenfalls durch Fluor, Chlor, Methyl oder Ethyl substituiertes Phenoxy-C1-C4-alkyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Amino, Methyl oder Ethyl substituiertes Pyridyloxy-C1-C4-alkyl, Pyrimidyloxy-C1-C4- alkyl und Thiazolyloxy-C1-C4-alkyl steht, R 1 represents in each case optionally substituted by fluorine or chlorine, C 1 - C 14 alkyl, C 2 -C 14 alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 alkyl, C 1 -C 4 alkylthio C 1 -C 6 alkyl, poly-C 1 -C 4 alkoxy-C 1 -C 4 alkyl or optionally by fluorine, chlorine, methyl, ethyl, propyl, i-propyl, butyl, i-butyl or tert. -Butyl substituted C 3 -C 6 cycloalkyl, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur, for phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl or nitro, for optionally substituted by fluorine, chlorine, bromine, methyl, Ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, benzyl substituted for furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, optionally substituted by fluorine, chlorine , Methyl or ethyl substituted phenoxy-C 1 -C 4 -alkyl, or for pyridyloxy-C 1 -C 4 -alkyl, pyrimidyloxy-C 1 -C 4 -alkyl and optionally substituted in each case by fluorine, chlorine, amino, methyl or ethyl Thiazolyloxy-C 1 -C 4 alkyl,
R2 für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1- C14-Alkyl, C3-C14-Alkenyl, C1-C4-Alkoxy-C1-C8-alkyl oder Poly- C1-C4-alkoxy-C1-C6-alkyl, für gegebenenfalls durch Fluor, Chlor, Methyl, Ethyl, Propyl, iso- Propyl oder Methoxy substituiertes C3-C6-Cycloalkyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Nitro, Methyl, Ethyl, Propyl, i-Propyl, Methoxy, Ethoxy oder Trifluormethyl substituiertes Phenyl oder Benzyl steht, R 2 represents in each case optionally substituted by fluorine or chlorine, C 1 - C 14 alkyl, C 3 -C 14 alkenyl, C 1 -C 4 -alkoxy-C 1 -C 8 -alkyl or poly-C 1 -C 4 - alkoxy-C 1 -C 6 alkyl, for C 3 -C 6 cycloalkyl optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl or methoxy, or for each optionally substituted by fluorine, chlorine, nitro, methyl, Ethyl, propyl, i-propyl, methoxy, ethoxy or trifluoromethyl-substituted phenyl or benzyl,
R3 für gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Methoxy, Trifluormethyl, Trifluormethoxy, Nitro oder Cyano substituiertes Phenyl oder Benzyl steht,
R4 und R5 unabhängig voneinander für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkyl- amino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylthio oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Nitro, Cyano, C1-C2-Alkoxy, C1-C2-Fluoralkoxy, C1-C2-Alkylthio, C1-C2-Fluoralkylthio oder C1-C3-Alkyl substituiertes Phenyl, Phenoxy oder Phenylthio stehen und R 3 represents C 1 -C 4 -alkyl which is optionally substituted by fluorine or chlorine or represents in each case phenyl or benzyl which is optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, R 4 and R 5 independently of one another for C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C 1 -C 4 - alkyl) amino, C 1 -C 4 alkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, C 1 -C 2 alkylthio , C 1 -C 2 fluoroalkylthio or C 1 -C 3 alkyl substituted phenyl, phenoxy or phenylthio and
R6 und R7 unabhängig voneinander für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C4- Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C3-C4- Alkenyl, C1-C4-Alkoxy-C1-C4-alkyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1- C4-Halogenalkyl, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, für gegebenenfalls durch Fluor, Chlor, Brom, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxy substituiertes Benzyl, oder zusammen für C4-C6-Alkandiyl stehen, worin gegebenenfalls eine Methylengruppe durch Sauerstoff oder Schwefel ersetzt ist. R 6 and R 7 independently of one another represent hydrogen, represent optionally fluorine-, chlorine- or bromine-substituted C 1 -C 4 - alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 - Alkenyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, for optionally by fluorine, chlorine, bromine, C 1 - C 4 haloalkyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituted phenyl, optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy, or together represent C 4 -C 6 alkanediyl, wherein a methylene group is optionally replaced by oxygen or sulfur.
Verfahren zur Herstellung von Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß man zum Erhalt von A process for the preparation of compounds of formula (I) according to claim 1, characterized in that to obtain
(A) 3-Thienylpyrrolidin-2,4-dionen bzw. deren Enolen der Formel (I-1-a) (A) 3-thienylpyrrolidine-2,4-diones or their enols of the formula (I-1-a)
in welcher in which
A, B, D, X und n die in Anspruch 1 angegebenen Bedeutungen haben, A, B, D, X and n have the meanings given in Claim 1,
N-Acylaminosäureester der Formel (II)
N-acylamino acid esters of the formula (II)
in welcher in which
A, B, D, X und n die oben angegebenen Bedeutungen haben, und A, B, D, X and n have the meanings given above, and
R8 für Alkyl steht, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular kondensiert, R 8 represents alkyl, intramolecularly condensed in the presence of a diluent and in the presence of a base,
(B) 3-Thienyl-4-hydroxy-Δ3-dihydrofuranon-Derivaten der Formel (I-2- a) (B) 3-thienyl-4-hydroxy-Δ 3 -dihydrofuranone derivatives of the formula (I-2- a)
in welcher in which
A, B, X und n die oben angegebenen Bedeutungen haben, A, B, X and n have the meanings given above,
Carbon säureester der Formel (III) Carboxylic acid esters of formula (III)
)
in welcher ) in which
A, B, X, R8 und n die oben angegebenen Bedeutungen haben, in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular kondensiert, (C) 3-Thienyl-4-hydroxy-Δ3-dihydrothiophenon-Derivaten der Formel (I- 3-a) A, B, X, R 8 and n have the meanings given above, intramolecularly condensed in the presence of a diluent and in the presence of a base, (C) 3-thienyl-4-hydroxy-Δ 3 -dihydrothiophenone derivatives of the formula (I- 3-a)
in welcher in which
A, B, X und n die oben angegebenen Bedeutungen haben, ß-Ketocarbonsäureester der Formel (IV) A, B, X and n have the meanings given above, β-ketocarboxylic acid esters of the formula (IV)
in welcher in which
A, B, X, R8 und n die oben angegebenen Bedeutungen haben und A, B, X, R 8 and n have the meanings given above and
W für Wasserstoff, Halogen, Alkyl oder Alkoxy steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und inW represents hydrogen, halogen, alkyl or alkoxy, optionally in the presence of a diluent and in
Gegenwart einer Säure intramolekular cyclisiert,
(D) 3-Hydroxy-4-thienyl-5-oxo-pyrazolinen der Formel (I-4-a) Presence of an acid cyclized intramolecularly, (D) 3-hydroxy-4-thienyl-5-oxopyrazolines of the formula (I-4-a)
in welcher in which
A, D, X und n die oben angegebenen Bedeutungen haben, A, D, X and n have the meanings given above,
(α) Halogencarbonylketene der Formel (V) (α) halocarbonyl ketene of the formula (V)
in welcher in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Halogen steht, Hal stands for halogen,
oder or
(ß) Malonsäurederivate der Formel (VI)
in welcher (β) malonic acid derivatives of the formula (VI) in which
R8, X und n die oben angegebenen Bedeutungen haben, mit Hydrazinen der Formel (VII) A-NH-NH-D (VII) in welcher R 8 , X and n have the meanings given above, with hydrazines of the formula (VII) A-NH-NH-D (VII) in which
A und D die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base umsetzt, (E) 3-Thienylpyron-Derivaten der Formel (I-5-a) A and D have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base, (E) 3-thienylpyrone derivatives of the formula (I-5-a)
in welcher in which
A, D, X und n die oben angegebenen Bedeutungen haben, A, D, X and n have the meanings given above,
Carbonylverbindungen der Formel (VIII)
2 in welcher Carbonyl compounds of formula (VIII) 2 in which
A und D die oben angegebenen Bedeutungen haben, mit Ketensäurehalogeniden der Formel (V) A and D have the meanings given above, with ketene acid halides of the formula (V)
in welcher in which
X und n die oben angegebenen Bedeutungen haben und X and n have the meanings given above and
Hal für Halogen steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säureakzeptors umsetzt, Hal represents halogen, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
(F) Thienyl-1,3-thiazin-Derivaten der Formel (I-6-a) (F) thienyl-1,3-thiazine derivatives of the formula (I-6-a)
in welcher in which
A, X und n die oben angegebenen Bedeutungen haben, Thioamide der Formel (IX)
A, X and n have the meanings given above, thioamides of the formula (IX)
in welcher in which
A die oben angegebene Bedeutung hat, mit Ketensäurehalogeniden der Formel (V) A has the meaning given above, with ketene acid halides of the formula (V)
in welcher in which
Hal, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säureakzeptors umsetzt, (G) 2-Thienyl-3-hydroxy-Δ2-cyclopenten-I-on-Derivaten der Formel (I- 7-a) Hal, X and n have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, (G) 2-thienyl-3-hydroxy-Δ 2 -cyclopenten-I-one derivatives of the formula (I- 7-a)
in welcher in which
A, B, D, Q1, X und n die in Anspruch 1 angegebenen Bedeutungen haben, A, B, D, Q 1 , X and n have the meanings given in Claim 1,
Ketocarbonsäureester der Formel (X)
in welcher Ketocarboxylic acid esters of the formula (X) in which
A, B, D, R8, Q1, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular cyclisiert, A, B, D, R 8 , Q 1 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base,
(H) 2-Thienyl-3-hydroxy-Δ2-cyclohexen-1-on-Derivaten der Formel (I-8- a) (H) 2-thienyl-3-hydroxy-Δ 2 -cyclohexen-1-one derivatives of the formula (I-8-a)
in welcher in which
A, B, D, Q , Q , Q , X und n die in Anspruch 1 angegebenen A, B, D, Q, Q, Q, X and n are those specified in claim 1
Bedeutungen haben, Have meanings
Ketocarbonsäureester der Formel (XI) Ketocarboxylic acid esters of the formula (XI)
in welcher
A, B, D, Q1, Q2, Q3, R8, X und n die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular cyclisiert, und gegebenenfalls die so erhaltenen Verbindungen der Formeln (I- 1-a) bis (I-8-a) jeweils in which A, B, D, Q 1 , Q 2 , Q 3 , R 8 , X and n have the meanings given above, optionally cyclized intramolecularly in the presence of a diluent and in the presence of a base, and optionally the compounds of the formulas (I - 1-a) to (I-8-a) each
(Iα) mit Säurehalogeniden der Formel (XII) (Iα) with acid halides of the formula (XII)
in welcher R1 die in Anspruch 1 angegebene Bedeutung hat und in which R 1 has the meaning given in claim 1 and
Hal für Halogen steht oder Hal stands for halogen or
(Iß) mit Carbonsäureanhydriden der Formel (XIII) (Iß) with carboxylic anhydrides of the formula (XIII)
R1-CO-O-CO-R1 (XIII) in welcher R 1 -CO-O-CO-R 1 (XIII) in which
R1 die oben angegebene Bedeutung hat, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt; oder (J) mit Chlorameisensaureestern oder Chlorameisensäurethioestern derR 1 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; or (J) with chloroformate or chloroformate thioester
Formel (XIV)
R2-M-CO-Cl (XIV) in welcher Formula (XIV) R 2 -M-CO-Cl (XIV) in which
R2 und M die in Anspruch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt; oder R 2 and M have the meanings given in claim 1, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; or
(Kα) mit Chlormonothioameisensäureestern oder Chlordithioameisensäureestern der Formel (XV)
in welcher (Kα) with chloromothio formic acid esters or chlorodithio formic acid esters of the formula (XV) in which
M und R2 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt oder (Kß) mit Schwefelkohlenstoff und anschließend mit Alkylhalogeniden derM and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or (Kß) with carbon disulfide and then with alkyl halides
Formel (XVI) Formula (XVI)
R2-Hal (XVI) in welcher R 2 -Hal (XVI) in which
R2 die oben angegebene Bedeutung hat und R 2 has the meaning given above and
Hal für Chlor, Brom oder Iod steht,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base umsetzt, oder Hal represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or
(L) mit Sulfonsäurechloriden der Formel (XVII) R3-SO2-Cl (XVII) in welcher (L) with sulfonic acid chlorides of the formula (XVII) R 3 -SO 2 -Cl (XVII) in which
R3 die in Anspruch 1 angegebene Bedeutung hat, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt, oder R 3 has the meaning given in claim 1, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or
(M) mit Phosphorverbindungen der Formel (XVIII) (M) with phosphorus compounds of the formula (XVIII)
in welcher in which
L, R4 und R5 die in Anspruch 1 angegebenen Bedeutungen haben und L, R 4 and R 5 have the meanings given in claim 1 and
Hal für Halogen steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt, oder (N) mit Metall Verbindungen oder Aminen der Formeln (XIX) oder (XX)
Me(OR10)t (XIX)Hal represents halogen, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or (N) with metal compounds or amines of the formulas (XIX) or (XX) Me (OR 10 ) t (XIX)
in welchen in which
Me für ein ein- oder zweiwertiges Metall, t für die Zahl 1 oder 2 und R10, R11, R12 unabhängig voneinander für Wasserstoff oder Alkyl stehen, gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder Me stands for a mono- or divalent metal, t for the number 1 or 2 and R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl, if appropriate in the presence of a diluent, or
(Oα) mit Isocyanaten oder Isothiocyanaten der Formel (XXI) R6-N=C=L (XXI) in welcher (Oα) with isocyanates or isothiocyanates of the formula (XXI) R 6 -N = C = L (XXI) in which
R6 und L die in Anspruch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators umsetzt oder R 6 and L have the meanings given in claim 1, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
(Oß) mit Carbamidsäurechloriden oder Thiocarbamidsäurechloriden der Formel (XXII) (Oß) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XXII)
in welcher in which
L, R6 und R7 die in Anspmch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels, umsetzt. 6. Verbindungen der Formel (II) L, R 6 and R 7 have the meanings given in Claim 1, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. 6. Compounds of formula (II)
in welcher in which
A, B, D, X und n die in Anspmch 1 angegebenen Bedeutungen haben und R8 für Alkyl steht. A, B, D, X and n have the meanings given in Claim 1 and R 8 represents alkyl.
7. Verbindungen der Formel (XXV) 7. Compounds of formula (XXV)
in welcher in which
A, B, D, X und n die in Anspmch 1 angegebenen Bedeutungen haben. 8. Verbindungen der Formel (XVIII)
A, B, D, X and n have the meanings given in Claim 1. 8. Compounds of the formula (XVIII)
in welcher in which
A, B, D, X und n die in Anspmch 1 angegebenen Bedeutungen haben. A, B, D, X and n have the meanings given in Claim 1.
9. Verbindungen der Formel (III) 9. Compounds of formula (III)
in welcher in which
A, B, X und n die in Anspmch 1 angegebenen Bedeutungen haben und A, B, X and n have the meanings given in Claim 1 and
R8 für Alkyl steht. 10. Verbindungen der Formel (IV) R 8 represents alkyl. 10. Compounds of the formula (IV)
in welcher in which
A, B, W, X und n die in Anspmch 1 angegebenen Bedeutungen haben und
R8 für Alkyl steht. 1. Verbindungen der Formel (V) A, B, W, X and n have the meanings given in Claim 1 and R 8 represents alkyl. 1. Compounds of formula (V)
in welcher in which
X und n die in Anspmch 1 angegebenen Bedeutungen haben und X and n have the meanings given in Claim 1 and
Hal für Chlor oder Brom steht. Hal stands for chlorine or bromine.
12. Verbindungen der Formel (X) 12. Compounds of the formula (X)
in welcher A, B, D, Q1, X und n die in Anspmch 1 angegebenen Bedeutungen haben und in which A, B, D, Q 1 , X and n have the meanings given in Claim 1 and
R8 für Alkyl steht. R 8 represents alkyl.
13. Verbindungen der Formel (XXXV) 13. Compounds of the formula (XXXV)
in welcher
A, B, D, Q1, X und n die in Anspmch 1 angegebenen Bedeutungen haben. 14. Verbindungen der Formel (XXXVIII) in which A, B, D, Q 1 , X and n have the meanings given in Claim 1. 14. Compounds of the formula (XXXVIII)
(XXXVIII)
(XXXVIII)
in welcher in which
A, B, D, Q1, X und n die in Anspmch 1 angegebenen Bedeutungen haben und A, B, D, Q 1 , X and n have the meanings given in Claim 1 and
R8 und R8' für Alkyl stehen. R 8 and R 8 'are alkyl.
15. Verbindungen der Formel (XI) 15. Compounds of the formula (XI)
in welcher in which
A, B, D, Q1, Q2, Q3, X und n die in Anspmch 1 angegebenen Bedeutungen haben und A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given in Claim 1 and
R8 für Alkyl steht. 16. Verbindungen der Formel (XL)
in welcher R 8 represents alkyl. 16. Compounds of the formula (XL) in which
A, B, D, Q1, Q2, Q3, X und n die in Anspmch 1 angegebenen Bedeutungen haben Verbindungen der Formel (XLII) A, B, D, Q 1 , Q 2 , Q 3 , X and n have the meanings given in Claim 1, compounds of the formula (XLII)
in welcher in which
A, B, D, Q1, Q2, Q3 Z und n die in Anspmch 1 angegebenen Bedeutungen haben und R8 und R8' für Alkyl stehen Schädlingsbekämpfungsmittel und Unkrautbekämpfungsmittel, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung der Formel (I) gemäß Anspmch 1 Verwendung von Verbindungen der Formel (I) gemäß Anspmch 1 zur Bekämpfung von Schädlingen und Unkräutern Verfahren zur Bekämpfung von Schädlingen und Unkräutern, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) gemäß Anspmch 1 auf Schädlinge und/oder ihren Lebensraum einwirken laßt oder auf Unkräuter und/oder ihren Lebensraum einwirken laßt Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln und Unkrautbekämpfungsmitteln, dadurch gekennzeichnet, daß man Verbindungen der
Formel (I) gemäß Anspmch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt. A, B, D, Q 1 , Q 2 , Q 3 Z and n have the meanings given in Claim 1 and R 8 and R 8 'represent alkyl pesticides and weed killers, characterized by a content of at least one compound of the formula (I ) according to Claim 1, use of compounds of the formula (I) according to Claim 1 for controlling pests and weeds, method for controlling pests and weeds, characterized in that compounds of the formula (I) according to Claim 1 are used for pests and / or their habitat allows to act or to act on weeds and / or their habitat processes for the production of pesticides and weed killers, characterized in that compounds of Formula (I) according to Claim 1 mixed with extenders and / or surface-active agents.
22. Verwendung von Verbindungen der Formel (I) gemäß Anspmch 1 zur22. Use of compounds of formula (I) according to Anspmch 1 for
Herstellung von Schädlingsbekämpfungsmitteln oder Unkrautbekämpfungsmittein.
Manufacture of pesticides or weed control agents.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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DE4440899 | 1994-11-17 | ||
DE4440899 | 1994-11-17 | ||
DE19527190A DE19527190A1 (en) | 1994-11-17 | 1995-07-26 | Thiophene derivatives |
DE19527190 | 1995-07-26 | ||
PCT/EP1995/004355 WO1996016061A1 (en) | 1994-11-17 | 1995-11-06 | Substituted thiophene derivatives as pesticides and herbicides |
Publications (1)
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EP0792272A1 true EP0792272A1 (en) | 1997-09-03 |
Family
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EP95937871A Ceased EP0792272A1 (en) | 1994-11-17 | 1995-11-06 | Substituted thiophene derivatives as pesticides and herbicides |
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US (3) | US5807805A (en) |
EP (1) | EP0792272A1 (en) |
JP (1) | JPH10509155A (en) |
AU (1) | AU3871095A (en) |
BR (1) | BR9509793A (en) |
WO (1) | WO1996016061A1 (en) |
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---|---|---|---|---|
DE10007411A1 (en) * | 2000-02-18 | 2001-08-23 | Bayer Ag | Active ingredient combinations with insecticidal and acaricidal properties |
DE10013914A1 (en) | 2000-03-21 | 2001-09-27 | Bayer Ag | Synergistic pesticidal composition comprising 4-hydroxy-3-phenyl-furan-2(5H)-one derivative and bifenazate, abamectin or bifenthrin, are useful as insecticide, acaricide, ectoparasiticide or antifouling agents |
DE10015310A1 (en) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Active ingredient combinations with insecticidal and acaricidal properties |
DE10017881A1 (en) * | 2000-04-11 | 2001-10-25 | Bayer Ag | Active ingredient combinations with insecticidal and acaricidal properties |
DE10018370A1 (en) * | 2000-04-14 | 2001-10-18 | Bayer Ag | Synergistic pesticidal composition containing phenyl-substituted furanone compound and e.g. chlorfluazuron, emamectin, endosulfan, fibronil or azadirachtin, especially useful as insecticide or acaricide |
DE10029077A1 (en) * | 2000-06-13 | 2001-12-20 | Bayer Ag | New heterocyclic-substituted thiazole derivatives, useful as total or selective herbicides, insecticides, acaricides, nematocides, ectoparasiticides or antifouling agents |
DE10062422A1 (en) * | 2000-12-14 | 2002-06-20 | Bayer Ag | Use of acetyl-CoA carboxylase to identify insecticidal use |
DE10152005A1 (en) | 2001-10-22 | 2003-04-30 | Bayer Cropscience Ag | Pyrazolyl substituted heterocycles |
US7967407B2 (en) * | 2006-02-03 | 2011-06-28 | R.R. Donnelley | Use of a sense mark to control a printing system |
DE102006027732A1 (en) | 2006-06-16 | 2008-01-10 | Bayer Cropscience Ag | Drug combinations with insecticidal and acaricidal properties |
DE102006027730A1 (en) * | 2006-06-16 | 2007-12-20 | Bayer Cropscience Ag | Drug combinations with insecticidal and acaricidal properties |
GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
GB0714981D0 (en) | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
GB0717082D0 (en) | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
US8404260B2 (en) | 2008-04-02 | 2013-03-26 | Bayer Cropscience Lp | Synergistic pesticide compositions |
MX2012001158A (en) | 2009-07-31 | 2012-02-13 | Syngenta Ltd | Herbicidally active heteroaryl-sî¥bstitî¥ted cyclic diones or derivatives thereof. |
CR20230186A (en) | 2020-09-30 | 2023-08-24 | Control Solutions Inc | Powder pest control compositions and methods of using |
US20220272980A1 (en) | 2021-03-01 | 2022-09-01 | Control Solutions, Inc. | Solid particulate pest control compositions and methods |
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US5258360A (en) * | 1986-04-17 | 1993-11-02 | Imperial Chemical Industries Plc | Alphamethoxy acrylic acid derivatives as fungicides |
US4985063A (en) * | 1988-08-20 | 1991-01-15 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-diones |
US5207817A (en) * | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
DE4014420A1 (en) * | 1989-09-23 | 1991-04-04 | Bayer Ag | 5H-FURAN-2-ON DERIVATIVES |
DE4216814A1 (en) * | 1991-07-16 | 1993-01-21 | Bayer Ag | 3-ARYL-4-HYDROXY- (DELTA) (UP ARROW) 3 (UP ARROW) -DIHYDROFURANONE- AND 3-ARYL-4-HYDROXY- (DELTA) (UP ARROW) 3 (UP ARROW) -DIHYDROTHIOPHENONE DERIVATIVES |
DE4213149A1 (en) * | 1992-04-22 | 1993-10-28 | Hoechst Ag | Acaricidal, insecticidal and nematicidal substituted (hetero) aryl-alkyl-ketone oxime-O-ether, process for their preparation, compositions containing them and their use as pesticides |
DE4236400A1 (en) * | 1992-10-28 | 1994-05-05 | Bayer Ag | N-phenylacetaminonitrile |
DE4413669A1 (en) * | 1993-07-05 | 1995-01-12 | Bayer Ag | Substituted aryl ketoenol heterocycles |
DE4410420A1 (en) * | 1994-03-25 | 1995-09-28 | Bayer Ag | 3-aryl-4-hydroxy-DELTA · 3 · -dihydrothiophenone derivatives |
US5869427A (en) * | 1996-06-11 | 1999-02-09 | Mitsui Chemicals, Inc. | Substituted thiophene derivative and plant disease control agent comprising the same as active ingredient |
-
1995
- 1995-11-06 EP EP95937871A patent/EP0792272A1/en not_active Ceased
- 1995-11-06 BR BR9509793A patent/BR9509793A/en not_active Application Discontinuation
- 1995-11-06 US US08/836,336 patent/US5807805A/en not_active Expired - Fee Related
- 1995-11-06 AU AU38710/95A patent/AU3871095A/en not_active Abandoned
- 1995-11-06 WO PCT/EP1995/004355 patent/WO1996016061A1/en not_active Application Discontinuation
- 1995-11-06 JP JP8516491A patent/JPH10509155A/en not_active Expired - Lifetime
-
1998
- 1998-06-03 US US09/089,945 patent/US6025383A/en not_active Expired - Fee Related
-
1999
- 1999-06-24 US US09/339,782 patent/US6100220A/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
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See references of WO9616061A1 * |
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US5807805A (en) | 1998-09-15 |
JPH10509155A (en) | 1998-09-08 |
WO1996016061A1 (en) | 1996-05-30 |
US6025383A (en) | 2000-02-15 |
AU3871095A (en) | 1996-06-17 |
US6100220A (en) | 2000-08-08 |
BR9509793A (en) | 1997-09-30 |
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