DE4125246C1 - - Google Patents
Info
- Publication number
- DE4125246C1 DE4125246C1 DE19914125246 DE4125246A DE4125246C1 DE 4125246 C1 DE4125246 C1 DE 4125246C1 DE 19914125246 DE19914125246 DE 19914125246 DE 4125246 A DE4125246 A DE 4125246A DE 4125246 C1 DE4125246 C1 DE 4125246C1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- radical
- alkyl radical
- derivative
- fluoro
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims description 14
- -1 [1,2,4] -thiadiazol-3-ylidenamino Chemical group 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- FLLSVYRURBJWRO-UHFFFAOYSA-N 1-iminothiadiazole Chemical compound N=S1N=NC=C1 FLLSVYRURBJWRO-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- AHFWKTKIRQCWCQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-amine Chemical class NC1=CCCN1 AHFWKTKIRQCWCQ-UHFFFAOYSA-N 0.000 claims description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- UFHAERUEUDENGS-UHFFFAOYSA-N 2-(2-acetamido-4-amino-5-fluorophenoxy)acetic acid Chemical compound CC(=O)NC1=CC(N)=C(F)C=C1OCC(O)=O UFHAERUEUDENGS-UHFFFAOYSA-N 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000003444 phase transfer catalyst Substances 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QXEBVQYRXDLQEY-UHFFFAOYSA-N 2-(2-acetamido-5-fluoro-4-isothiocyanatophenoxy)acetic acid Chemical compound CC(=O)NC1=CC(N=C=S)=C(F)C=C1OCC(O)=O QXEBVQYRXDLQEY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- NDTHRWDAUORQSQ-UHFFFAOYSA-N n-(4-fluoro-2-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1O NDTHRWDAUORQSQ-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OOYHSZQSVUROMJ-UHFFFAOYSA-N 2-(2-acetamido-5-fluoro-4-nitrophenoxy)acetic acid Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=C(F)C=C1OCC(O)=O OOYHSZQSVUROMJ-UHFFFAOYSA-N 0.000 description 2
- OODQURJJHQBUFM-UHFFFAOYSA-N 2-(2-acetamido-5-fluorophenoxy)acetic acid Chemical compound CC(=O)NC1=CC=C(F)C=C1OCC(O)=O OODQURJJHQBUFM-UHFFFAOYSA-N 0.000 description 2
- LWMAFJZTZAMNGG-UHFFFAOYSA-N 6-amino-7-fluoro-4h-1,4-benzoxazin-3-one Chemical class N1C(=O)COC2=C1C=C(N)C(F)=C2 LWMAFJZTZAMNGG-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- XICDQDGOZAJHQD-UHFFFAOYSA-N O1CC(=O)NC2=C1C=C(F)C(N=C1N3CCCC3=NS1)=C2 Chemical class O1CC(=O)NC2=C1C=C(F)C(N=C1N3CCCC3=NS1)=C2 XICDQDGOZAJHQD-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IIDUNAVOCYMUFB-UHFFFAOYSA-N 2-amino-5-fluorophenol Chemical compound NC1=CC=C(F)C=C1O IIDUNAVOCYMUFB-UHFFFAOYSA-N 0.000 description 1
- HEXSLVTZXWZKHY-UHFFFAOYSA-N 2-fluoro-2-phenoxyacetic acid Chemical compound OC(=O)C(F)OC1=CC=CC=C1 HEXSLVTZXWZKHY-UHFFFAOYSA-N 0.000 description 1
- MNNRROMROMAXDR-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydropyrrol-5-amine Chemical compound CC1(C)CN=C(N)C1 MNNRROMROMAXDR-UHFFFAOYSA-N 0.000 description 1
- UMTAYFACVDWHNP-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydropyrrol-5-amine;methyl hydrogen sulfate Chemical compound COS(O)(=O)=O.CC1(C)CN=C(N)C1 UMTAYFACVDWHNP-UHFFFAOYSA-N 0.000 description 1
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 description 1
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical group C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 1
- LREXGCZCUDIQBO-UHFFFAOYSA-N 7-fluoro-4h-1,2-benzoxazin-3-one Chemical class C1C(=O)NOC2=CC(F)=CC=C21 LREXGCZCUDIQBO-UHFFFAOYSA-N 0.000 description 1
- AMGHIXJIXQAGFA-UHFFFAOYSA-N CCC(C(=O)O)OC1=C(C=C(C(=C1)F)N)NC(=O)C Chemical compound CCC(C(=O)O)OC1=C(C=C(C(=C1)F)N)NC(=O)C AMGHIXJIXQAGFA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- OVDPAWTVQWNIIC-UHFFFAOYSA-N ethyl 2-(2-acetamido-4-amino-5-fluorophenoxy)acetate Chemical compound CCOC(=O)COC1=CC(F)=C(N)C=C1NC(C)=O OVDPAWTVQWNIIC-UHFFFAOYSA-N 0.000 description 1
- LXHDTIJGOQAZSC-UHFFFAOYSA-N ethyl 2-(2-acetamido-5-fluoro-4-nitrophenoxy)acetate Chemical compound CCOC(=O)COC1=CC(F)=C([N+]([O-])=O)C=C1NC(C)=O LXHDTIJGOQAZSC-UHFFFAOYSA-N 0.000 description 1
- NVAGNZZHZGRPMF-UHFFFAOYSA-N ethyl 2-(2-acetamido-5-fluorophenoxy)acetate Chemical compound CCOC(=O)COC1=CC(F)=CC=C1NC(C)=O NVAGNZZHZGRPMF-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914125246 DE4125246C1 (sv) | 1991-07-26 | 1991-07-26 | |
| EP92916316A EP0596963A1 (de) | 1991-07-26 | 1992-07-22 | VERFAHREN UND ZWISCHENPRODUKTE ZUR HERSTELLUNG VON SUBSTITUIERTEN 6-(3,5,6,7-TETRAHYDROPYRROLO 2,1-c] 1,2,4]THIADIAZOL-3-YLIDENAMINO)-7-FLUOR-2H-1,4-BENZOXAZIN-3(4H)-ONEN |
| PCT/DE1992/000606 WO1993003043A1 (de) | 1991-07-26 | 1992-07-22 | VERFAHREN UND ZWISCHENPRODUKTE ZUR HERSTELLUNG VON SUBSTITUIERTEN 6-(3,5,6,7-TETRAHYDROPYRROLO[2,1-c][1,2,4]THIADIAZOL-3-YLIDENAMINO)-7-FLUOR-2H-1,4-BENZOXAZIN-3(4H)-ONEN |
| JP5503172A JPH06509345A (ja) | 1991-07-26 | 1992-07-22 | 置換された６−（３，５，６，７−テトラヒドロピロロ［２，１−ｃ］［１，２，４］チアジアゾル−３−イリデンアミノ）−７−フルオル−２Ｈ−１，４−ベンゾオキサジン−３（４Ｈ）−オンの製造のための方法及び中間体 |
| PT10072792A PT100727A (pt) | 1991-07-26 | 1992-07-24 | Processo e produtos intermediarios para a preparacao de 6-(3,5,6,7-tetrahidropirrolo{2,1-c}{1,2,4} tiadiazol-3-ilidenoamino)-7-fluor-2h-1,benzoxazino-3(4)-onas substituidas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914125246 DE4125246C1 (sv) | 1991-07-26 | 1991-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4125246C1 true DE4125246C1 (sv) | 1993-02-04 |
Family
ID=6437332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19914125246 Expired - Lifetime DE4125246C1 (sv) | 1991-07-26 | 1991-07-26 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0596963A1 (sv) |
| JP (1) | JPH06509345A (sv) |
| DE (1) | DE4125246C1 (sv) |
| PT (1) | PT100727A (sv) |
| WO (1) | WO1993003043A1 (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013540113A (ja) | 2010-10-01 | 2013-10-31 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草性ベンゾオキサジノン |
| CN111356693A (zh) | 2017-11-23 | 2020-06-30 | 巴斯夫欧洲公司 | 除草的苯基醚类 |
| AU2018373436C1 (en) | 2017-11-23 | 2023-10-19 | Basf Se | Herbicidal pyridylethers |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0170191A2 (en) * | 1984-07-23 | 1986-02-05 | Sumitomo Chemical Company, Limited | Tetrahydrophtalimides, and their production and use |
| WO1988005263A1 (en) * | 1987-01-15 | 1988-07-28 | Fmc Corporation | Triazinedione herbicides |
| WO1988005265A1 (en) * | 1987-01-15 | 1988-07-28 | Fmc Corporation | Tetrazolinone herbicides |
| EP0304935A1 (en) * | 1987-08-27 | 1989-03-01 | Sumitomo Chemical Company, Limited | Tetrahydroindazolyl-benzoxazines, their production and use |
| EP0311135A2 (de) * | 1987-10-09 | 1989-04-12 | Schering Aktiengesellschaft | Heterocyclisch substituierte Azole und Azine, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung |
| EP0422639A1 (en) * | 1989-10-12 | 1991-04-17 | Sumitomo Chemical Company, Limited | Benzoxazinyl-pyrazoles, and their production and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448188A3 (en) * | 1990-03-15 | 1992-02-26 | Schering Aktiengesellschaft | Process and intermediates for the preparation of substituted 6-(3,5,6,7-tetrahydropyrrolo-(2,1-c)(1,2,4)-thiadiazol-3-ylidenimino)-7-fluoro-2h-1,4-benzoxazin-3(4h)-ones |
-
1991
- 1991-07-26 DE DE19914125246 patent/DE4125246C1/de not_active Expired - Lifetime
-
1992
- 1992-07-22 JP JP5503172A patent/JPH06509345A/ja active Pending
- 1992-07-22 WO PCT/DE1992/000606 patent/WO1993003043A1/de not_active Application Discontinuation
- 1992-07-22 EP EP92916316A patent/EP0596963A1/de not_active Withdrawn
- 1992-07-24 PT PT10072792A patent/PT100727A/pt not_active Application Discontinuation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0170191A2 (en) * | 1984-07-23 | 1986-02-05 | Sumitomo Chemical Company, Limited | Tetrahydrophtalimides, and their production and use |
| WO1988005263A1 (en) * | 1987-01-15 | 1988-07-28 | Fmc Corporation | Triazinedione herbicides |
| WO1988005265A1 (en) * | 1987-01-15 | 1988-07-28 | Fmc Corporation | Tetrazolinone herbicides |
| EP0304935A1 (en) * | 1987-08-27 | 1989-03-01 | Sumitomo Chemical Company, Limited | Tetrahydroindazolyl-benzoxazines, their production and use |
| EP0311135A2 (de) * | 1987-10-09 | 1989-04-12 | Schering Aktiengesellschaft | Heterocyclisch substituierte Azole und Azine, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung |
| EP0422639A1 (en) * | 1989-10-12 | 1991-04-17 | Sumitomo Chemical Company, Limited | Benzoxazinyl-pyrazoles, and their production and use |
Non-Patent Citations (5)
| Title |
|---|
| HOUBEN-WEYL: Bd. VI/4 (1966), S. 554 * |
| JP-Kokai 1-1 25 351 * |
| JP-Kokai 1-1 25 354 * |
| JP-Kokai 1-1 25 355 * |
| JP-Kokai 1-1 25 356 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993003043A1 (de) | 1993-02-18 |
| JPH06509345A (ja) | 1994-10-20 |
| PT100727A (pt) | 1993-10-29 |
| EP0596963A1 (de) | 1994-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of the examined application without publication of unexamined application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SCHERING AG, 13353 BERLIN, DE |
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| 8330 | Complete disclaimer |