DE19742492A1 - Spirocyclische Phenylketoenole - Google Patents
Spirocyclische PhenylketoenoleInfo
- Publication number
- DE19742492A1 DE19742492A1 DE19742492A DE19742492A DE19742492A1 DE 19742492 A1 DE19742492 A1 DE 19742492A1 DE 19742492 A DE19742492 A DE 19742492A DE 19742492 A DE19742492 A DE 19742492A DE 19742492 A1 DE19742492 A1 DE 19742492A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- compounds
- meanings given
- spp
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims abstract description 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 239000004009 herbicide Substances 0.000 claims abstract description 11
- 239000000575 pesticide Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 144
- -1 phenoxy, phenylthio, benzyloxy Chemical group 0.000 claims description 95
- 239000002253 acid Substances 0.000 claims description 56
- 239000003085 diluting agent Substances 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 150000002367 halogens Chemical group 0.000 claims description 43
- 239000011230 binding agent Substances 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 241000196324 Embryophyta Species 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 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 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-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
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical class SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000013067 intermediate product Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- 239000000203 mixture Substances 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 38
- 229910052801 chlorine Inorganic materials 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000011737 fluorine Substances 0.000 description 31
- 229910052731 fluorine Inorganic materials 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 27
- 229910052794 bromium Inorganic materials 0.000 description 27
- 239000000126 substance Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 238000012360 testing method Methods 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001153 fluoro group Chemical group F* 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000002585 base Substances 0.000 description 14
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000002023 wood Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000002917 insecticide Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000011877 solvent mixture Substances 0.000 description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 7
- 241000238876 Acari Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 229940093956 potassium carbonate Drugs 0.000 description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241001177134 Lyctus Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 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 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 241000358422 Nephotettix cincticeps Species 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 241001481703 Rhipicephalus <genus> Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 4
- 239000000292 calcium oxide Substances 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
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- 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
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- 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
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- 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
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- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/12—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 condensed with a carbocyclic ring
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742492A DE19742492A1 (de) | 1997-09-26 | 1997-09-26 | Spirocyclische Phenylketoenole |
| TR2000/00749T TR200000749T2 (tr) | 1997-09-26 | 1998-09-12 | Spirosiklik fenilketoenoller. |
| DE59814345T DE59814345D1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
| AT98951386T ATE423097T1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
| KR1020007002590A KR100547508B1 (ko) | 1997-09-26 | 1998-09-12 | 농약 및 제초제로서의 스피로사이클릭 페닐 케토-에놀의용도 |
| PCT/EP1998/005809 WO1999016748A1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
| EP98951386A EP1017674B1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
| US09/509,288 US6589976B1 (en) | 1997-09-26 | 1998-09-12 | Utilizing spirocyclic phenyl keto-enols as pesticides and herbicides |
| AU97431/98A AU9743198A (en) | 1997-09-26 | 1998-09-12 | Utilizing spirocyclic phenyl keto-enols as pesticides and herbicides |
| BRPI9812535-4A BR9812535B1 (pt) | 1997-09-26 | 1998-09-12 | fenilcetoenóis espirocìclicos como pesticidas e como herbicidas, processo para a preparação dos mesmos, para o combate de pragas e de ervas daninhas e para a preparação de composições praguicidas e composições herbicidas, bem como composições praguicidas ou composições herbicidas e uso dos referidos compostos. |
| ES98951386T ES2320394T3 (es) | 1997-09-26 | 1998-09-12 | Fenilcetoenoles espirociclicos como pesticidas y herbicidas. |
| JP2000513834A JP4422891B2 (ja) | 1997-09-26 | 1998-09-12 | スピロ環式フェニルケト−エノール類の有害生物防除剤並びに除草剤としての使用 |
| CN988095572A CN1217931C (zh) | 1997-09-26 | 1998-09-12 | 作为杀虫剂和除草剂的螺环苯基酮烯醇 |
| TW087115725A TW568904B (en) | 1997-09-26 | 1998-09-22 | Spirocyclic phenylketoenols, the process for preparing them and their use as pesticide and herbicides |
| ZA988784A ZA988784B (en) | 1997-09-26 | 1998-09-25 | Spirocyclic phenylketoenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742492A DE19742492A1 (de) | 1997-09-26 | 1997-09-26 | Spirocyclische Phenylketoenole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19742492A1 true DE19742492A1 (de) | 1999-04-01 |
Family
ID=7843694
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742492A Withdrawn DE19742492A1 (de) | 1997-09-26 | 1997-09-26 | Spirocyclische Phenylketoenole |
| DE59814345T Expired - Lifetime DE59814345D1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59814345T Expired - Lifetime DE59814345D1 (de) | 1997-09-26 | 1998-09-12 | Spirocyclische phenylketoenole als pestizide und herbizide |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6589976B1 (https=) |
| EP (1) | EP1017674B1 (https=) |
| JP (1) | JP4422891B2 (https=) |
| KR (1) | KR100547508B1 (https=) |
| CN (1) | CN1217931C (https=) |
| AT (1) | ATE423097T1 (https=) |
| AU (1) | AU9743198A (https=) |
| BR (1) | BR9812535B1 (https=) |
| DE (2) | DE19742492A1 (https=) |
| ES (1) | ES2320394T3 (https=) |
| TR (1) | TR200000749T2 (https=) |
| TW (1) | TW568904B (https=) |
| WO (1) | WO1999016748A1 (https=) |
| ZA (1) | ZA988784B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019201842A1 (de) * | 2018-04-17 | 2019-10-24 | Bayer Aktiengesellschaft | Verfahren zur herstellung von estern n-acylierter aminosäuren mit säurelabilen keto-schutzgruppenfunktionen |
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| WO2019197620A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
| MX2020010686A (es) | 2018-04-13 | 2020-11-06 | Bayer Cropscience Ag | Uso de derivados del acido tetramico para el control de plagas por riego o aplicacion de gotas. |
| WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
| WO2019197652A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Feststoff-formulierung insektizider mischungen |
| CN112312768A (zh) | 2018-04-13 | 2021-02-02 | 拜耳作物科学股份公司 | 特特拉姆酸衍生物用于防治特定昆虫的用途 |
| WO2020126980A1 (en) * | 2018-12-18 | 2020-06-25 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
| BR112021009703A2 (pt) * | 2019-03-01 | 2021-11-23 | Bayer Ag | Combinações de compostos ativos tendo propriedades inseticidas/acaricidas |
| CN116940238A (zh) | 2020-09-30 | 2023-10-24 | 控制解决方案公司 | 粉末有害物防治组合物及使用方法 |
| BR112023017783A2 (pt) | 2021-03-01 | 2023-11-21 | Control Solutions Inc | Métodos e composições de controle de pragas em partículas sólidas |
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| DE4014420A1 (de) | 1989-09-23 | 1991-04-04 | Bayer Ag | 5h-furan-2-on-derivate |
| US5207817A (en) | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
| DE4107394A1 (de) | 1990-05-10 | 1991-11-14 | Bayer Ag | 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
| DE4121365A1 (de) | 1991-06-28 | 1993-01-14 | Bayer Ag | Substituierte 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
| DE4216814A1 (de) | 1991-07-16 | 1993-01-21 | Bayer Ag | 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrofuranon- und 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrothiophenon-derivate |
| AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
| DE4306257A1 (de) | 1993-03-01 | 1994-09-08 | Bayer Ag | Substituierte 1-H-3-Phenyl-5-cycloalkylpyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung |
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| EP0706527B1 (de) | 1993-07-02 | 2001-11-14 | Bayer Ag | Substituierte spiroheterocyclische 1h-3-aryl-pyrrolidin-2,4-dion-derivate, verfahren zu deren herstellung und deren verwendung als schädlingsbekämpfungsmittel |
| EP0647637B1 (de) | 1993-09-17 | 1999-01-27 | Bayer Ag | 3-Aryl-4-hydroxy-3-dihydrofuranon-Derivate |
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| DE4425617A1 (de) | 1994-01-28 | 1995-08-03 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| DE4431730A1 (de) * | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| AU2072695A (en) * | 1994-04-05 | 1995-10-23 | Bayer Aktiengesellschaft | Alkoxy-alkyl-substituted 1-h-3-aryl-pyrrolidine-2,4-diones used as herbicides and pesticides |
| CN1079798C (zh) | 1994-12-23 | 2002-02-27 | 拜尔公司 | 3－芳基－季酮酸衍生物、其生产和作为杀虫剂的应用和中间体 |
| AU4715896A (en) | 1995-02-13 | 1996-09-04 | Bayer Aktiengesellschaft | 2-phenyl-substituted heterocyclic 1,3-ketonols as herbicides and pesticides |
| AU5762696A (en) | 1995-05-09 | 1996-11-29 | Bayer Aktiengesellschaft | Alkyl dihalogenated phenyl-substituted ketoenols useful as p esticides and herbicides |
| DE19602524A1 (de) * | 1995-06-28 | 1997-01-02 | Bayer Ag | 2,4,5-Trisubstituierte Phenylketoenole |
| JP4082724B2 (ja) | 1995-06-28 | 2008-04-30 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤及び除草剤として使用される２，４，５−三置換されたフェニルケト−エノール |
| EP0835243B1 (de) | 1995-06-30 | 2003-01-29 | Bayer CropScience AG | Dialkyl-halogenphenylsubstituierte ketoenole zur verwendung als herbizide und pestizide |
| DE19603332A1 (de) * | 1995-06-30 | 1997-01-02 | Bayer Ag | Dialkyl-halogenphenylsubstituierte Ketoenole |
| BR9708425B1 (pt) | 1996-04-02 | 2012-02-22 | fenilcetoenóis substituìdos, processo para preparação e uso dos mesmos, bem como pesticidas ou herbicidas e método para controle de pragas e ervas daninhas. | |
| JP4202423B2 (ja) | 1996-08-05 | 2008-12-24 | バイエル・アクチエンゲゼルシヤフト | ２―および２，５―置換フェニルケトエノール |
-
1997
- 1997-09-26 DE DE19742492A patent/DE19742492A1/de not_active Withdrawn
-
1998
- 1998-09-12 AT AT98951386T patent/ATE423097T1/de active
- 1998-09-12 WO PCT/EP1998/005809 patent/WO1999016748A1/de not_active Ceased
- 1998-09-12 TR TR2000/00749T patent/TR200000749T2/xx unknown
- 1998-09-12 JP JP2000513834A patent/JP4422891B2/ja not_active Expired - Fee Related
- 1998-09-12 BR BRPI9812535-4A patent/BR9812535B1/pt not_active IP Right Cessation
- 1998-09-12 DE DE59814345T patent/DE59814345D1/de not_active Expired - Lifetime
- 1998-09-12 KR KR1020007002590A patent/KR100547508B1/ko not_active Expired - Fee Related
- 1998-09-12 US US09/509,288 patent/US6589976B1/en not_active Expired - Lifetime
- 1998-09-12 ES ES98951386T patent/ES2320394T3/es not_active Expired - Lifetime
- 1998-09-12 AU AU97431/98A patent/AU9743198A/en not_active Abandoned
- 1998-09-12 EP EP98951386A patent/EP1017674B1/de not_active Expired - Lifetime
- 1998-09-12 CN CN988095572A patent/CN1217931C/zh not_active Expired - Fee Related
- 1998-09-22 TW TW087115725A patent/TW568904B/zh not_active IP Right Cessation
- 1998-09-25 ZA ZA988784A patent/ZA988784B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019201842A1 (de) * | 2018-04-17 | 2019-10-24 | Bayer Aktiengesellschaft | Verfahren zur herstellung von estern n-acylierter aminosäuren mit säurelabilen keto-schutzgruppenfunktionen |
| US11384061B2 (en) | 2018-04-17 | 2022-07-12 | Bayer Aktiengesellschaft | Process for preparing esters of N-acylated amino acids with acid-labile keto protective group functions |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1271343A (zh) | 2000-10-25 |
| WO1999016748A1 (de) | 1999-04-08 |
| AU9743198A (en) | 1999-04-23 |
| KR100547508B1 (ko) | 2006-02-01 |
| BR9812535A (pt) | 2000-07-25 |
| DE59814345D1 (de) | 2009-04-02 |
| US6589976B1 (en) | 2003-07-08 |
| ATE423097T1 (de) | 2009-03-15 |
| JP2001518464A (ja) | 2001-10-16 |
| EP1017674B1 (de) | 2009-02-18 |
| KR20010023904A (ko) | 2001-03-26 |
| ZA988784B (en) | 1999-03-31 |
| JP4422891B2 (ja) | 2010-02-24 |
| ES2320394T3 (es) | 2009-05-21 |
| TR200000749T2 (tr) | 2000-08-21 |
| BR9812535B1 (pt) | 2009-12-01 |
| CN1217931C (zh) | 2005-09-07 |
| TW568904B (en) | 2004-01-01 |
| EP1017674A1 (de) | 2000-07-12 |
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