NO313880B1 - Substituerte pyrazol-3-ylbenzazoler, anvendelse derav og herbicid preparat basert pÕ disse, samt fremgangsmÕte forfremstilling derav - Google Patents
Substituerte pyrazol-3-ylbenzazoler, anvendelse derav og herbicid preparat basert pÕ disse, samt fremgangsmÕte forfremstilling derav Download PDFInfo
- Publication number
- NO313880B1 NO313880B1 NO19992924A NO992924A NO313880B1 NO 313880 B1 NO313880 B1 NO 313880B1 NO 19992924 A NO19992924 A NO 19992924A NO 992924 A NO992924 A NO 992924A NO 313880 B1 NO313880 B1 NO 313880B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- ylbenzazole
- substituted pyrazol
- alkyl
- pyrazol
- Prior art date
Links
- MZASQQDCQLEXBR-UHFFFAOYSA-N chembl2414979 Chemical class N1C=CC(C=2NC3=CC=CC=C3C=2)=N1 MZASQQDCQLEXBR-UHFFFAOYSA-N 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 34
- 230000002363 herbicidal effect Effects 0.000 title claims description 15
- -1 alkali metal thiocyanate Chemical class 0.000 claims description 389
- 150000001875 compounds Chemical class 0.000 claims description 129
- 238000006243 chemical reaction Methods 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 239000012954 diazonium Substances 0.000 claims description 12
- 150000001989 diazonium salts Chemical class 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 239000004009 herbicide Substances 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000002837 defoliant Substances 0.000 claims description 7
- 230000035613 defoliation Effects 0.000 claims description 7
- 239000002274 desiccant Substances 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- YLYPTGYHGCWJGN-UHFFFAOYSA-N 5-phenyl-1h-pyrazol-4-amine Chemical compound C1=NNC(C=2C=CC=CC=2)=C1N YLYPTGYHGCWJGN-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 5
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- VGQYGJXBIRIZQJ-UHFFFAOYSA-N 4-azido-5-phenyl-1h-pyrazole Chemical compound [N-]=[N+]=NC1=CNN=C1C1=CC=CC=C1 VGQYGJXBIRIZQJ-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
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- 241000196324 Embryophyta Species 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
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- 239000000243 solution Substances 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000011737 fluorine Substances 0.000 description 17
- 229910052731 fluorine Inorganic materials 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 239000012043 crude product Substances 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 11
- 239000012414 tert-butyl nitrite Substances 0.000 description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 10
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- 238000011282 treatment Methods 0.000 description 9
- HPYGAZZHZFOMNX-UHFFFAOYSA-N 2-bromo-4-chloro-7-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-6-fluoro-1,3-benzothiazole Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=C(F)C=C(Cl)C2=C1SC(Br)=N2 HPYGAZZHZFOMNX-UHFFFAOYSA-N 0.000 description 8
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- 239000007800 oxidant agent Substances 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- KAWBFWMQWATQFI-UHFFFAOYSA-N ethyl 2-[4-chloro-7-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-6-fluoro-1,3-benzothiazol-2-yl]acetate Chemical compound C=12SC(CC(=O)OCC)=NC2=C(Cl)C=C(F)C=1C1=NN(C)C(OC(F)F)=C1Cl KAWBFWMQWATQFI-UHFFFAOYSA-N 0.000 description 1
- JUHMHPOXZAYYJP-UHFFFAOYSA-N ethyl 5-amino-1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate Chemical class NC1=C(C(=O)OCC)C=NN1S(=O)(=O)C1=CC=C(C)C=C1 JUHMHPOXZAYYJP-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- HQZMRJBVCVYVQA-UHFFFAOYSA-N hydron;methyl 2-(methylamino)acetate;chloride Chemical compound Cl.CNCC(=O)OC HQZMRJBVCVYVQA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- DMTQTXVTYMCMAP-UHFFFAOYSA-N methyl 2-[[4-chloro-7-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-6-fluoro-1,3-benzothiazol-2-yl]amino]acetate Chemical compound C=12SC(NCC(=O)OC)=NC2=C(Cl)C=C(F)C=1C1=NN(C)C(OC(F)F)=C1Cl DMTQTXVTYMCMAP-UHFFFAOYSA-N 0.000 description 1
- MENLWYNMKDCZGH-UHFFFAOYSA-N methyl 2-[[4-chloro-7-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-6-fluoro-1,3-benzothiazol-2-yl]oxy]propanoate Chemical compound C=12SC(OC(C)C(=O)OC)=NC2=C(Cl)C=C(F)C=1C1=NN(C)C(OC(F)F)=C1Cl MENLWYNMKDCZGH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QUGNDMPFNZMDRO-UHFFFAOYSA-N n-[4-chloro-7-[4-chloro-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-6-fluoro-1,3-benzothiazol-2-yl]acetamide Chemical compound C=12SC(NC(=O)C)=NC2=C(Cl)C=C(F)C=1C1=NN(C)C(C(F)(F)F)=C1Cl QUGNDMPFNZMDRO-UHFFFAOYSA-N 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004322 oxepan-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 108700027361 sarcosine methyl ester Proteins 0.000 description 1
- VXGABWCSZZWXPC-UHFFFAOYSA-N sarcosine methyl ester hydrochloride Natural products CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004324 thiepan-2-yl group Chemical group [H]C1([H])SC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19652240 | 1996-12-16 | ||
| PCT/EP1997/006715 WO1998027090A2 (fr) | 1996-12-16 | 1997-12-01 | Pyrazol-3-ylbenzazoles substitues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992924D0 NO992924D0 (no) | 1999-06-15 |
| NO992924L NO992924L (no) | 1999-08-13 |
| NO313880B1 true NO313880B1 (no) | 2002-12-16 |
Family
ID=7814838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992924A NO313880B1 (no) | 1996-12-16 | 1999-06-15 | Substituerte pyrazol-3-ylbenzazoler, anvendelse derav og herbicid preparat basert pÕ disse, samt fremgangsmÕte forfremstilling derav |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6232470B1 (fr) |
| EP (1) | EP0944623B1 (fr) |
| JP (1) | JP2001506641A (fr) |
| KR (1) | KR20000057600A (fr) |
| CN (1) | CN1145626C (fr) |
| AR (1) | AR008943A1 (fr) |
| AT (1) | ATE275146T1 (fr) |
| AU (1) | AU744339B2 (fr) |
| BG (1) | BG63873B1 (fr) |
| BR (1) | BR9713947A (fr) |
| CA (1) | CA2275611A1 (fr) |
| DE (1) | DE59711889D1 (fr) |
| EA (1) | EA002350B1 (fr) |
| GE (1) | GEP20022859B (fr) |
| HU (1) | HUP0000543A3 (fr) |
| IL (1) | IL130469A (fr) |
| NO (1) | NO313880B1 (fr) |
| NZ (1) | NZ336368A (fr) |
| PL (1) | PL334253A1 (fr) |
| SK (1) | SK77899A3 (fr) |
| TR (1) | TR199901351T2 (fr) |
| TW (1) | TW474916B (fr) |
| UA (1) | UA53679C2 (fr) |
| WO (1) | WO1998027090A2 (fr) |
| ZA (1) | ZA9711235B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0998472A1 (fr) | 1997-07-14 | 2000-05-10 | Basf Aktiengesellschaft | 2-(benzaryl)pyridines substituees |
| EP1076660B1 (fr) * | 1998-04-29 | 2002-06-26 | Basf Aktiengesellschaft | (4-brompyrazol-3-yl)benzazoles substitues |
| US6573218B1 (en) | 1998-09-09 | 2003-06-03 | Ishihara Sangyo Kaisha, Ltd. | Fused-benzene derivatives useful as herbicides |
| DE50103231D1 (de) * | 2000-03-16 | 2004-09-16 | Basf Ag | Verfahren zur herstellung von 7-(pyrazol-3-yl)benzoxazolen |
| TW200305368A (en) * | 2001-12-19 | 2003-11-01 | Basf Ag | Herbicidal mixtures based on 7-pyrazolylbenzoxazoles |
| DE10235206A1 (de) * | 2002-08-01 | 2004-02-19 | Basf Ag | Verfahren zur Herstellung von (S)-3-Methylmino-1-(thien-2-yl)propan-1-ol |
| CN101279972B (zh) * | 2008-05-12 | 2011-02-02 | 大连理工大学 | 苯并噁唑类除草剂及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376122A (en) | 1981-07-13 | 1983-03-08 | American Cyanamid Company | Novel 3-substituted amino-1-heteroaryl-2-pyrazolines |
| DE3407506A1 (de) | 1984-03-01 | 1985-09-05 | A. Nattermann & Cie GmbH, 5000 Köln | 3-amino-1-(4,5,6,7-tetrahydro-benzothiazolyl)-2-pyrazoline, verfahren zu ihrer herstellung und deren verwendung |
| KR870007162A (ko) | 1986-01-29 | 1987-08-17 | 니시자와 요시히꼬 | 인다졸 화합물, 및 그의 제조방법과 용도 |
| DE3705935A1 (de) | 1987-02-25 | 1988-09-08 | Nattermann A & Cie | Ein eintopf-verfahren zur herstellung von 3-amino-1-(4,5,6,7-tetrahydro-2-benzothiazolyl)-2-pyrazolinen |
| DE3705933A1 (de) | 1987-02-25 | 1988-09-08 | Nattermann A & Cie | 3-n-arylamino-1-(4,5,6,7-tetrahydro-2- benzothiazolyl)-2-pyrazoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| JP2905981B2 (ja) | 1989-04-21 | 1999-06-14 | 日本農薬株式会社 | ３―置換フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤 |
| JP2905982B2 (ja) | 1989-05-02 | 1999-06-14 | 日本農薬株式会社 | 複素環含有フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤 |
| BR9106737A (pt) * | 1990-08-06 | 1993-08-31 | Monsanto Co | Aril alquilsulfonil pirazois substituidos herbicidas |
| US5281571A (en) * | 1990-10-18 | 1994-01-25 | Monsanto Company | Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles |
| DE4117508A1 (de) | 1991-05-24 | 1992-11-26 | Schering Ag | Substituierte benzthiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
| DE4241658A1 (de) | 1992-12-04 | 1994-06-09 | Schering Ag | Substituierte 2-Thiobenzthiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als herbizide Mittel |
| GB9413237D0 (en) | 1994-07-01 | 1994-08-24 | Zeneca Ltd | Herbicides |
| HRP950330A2 (en) * | 1994-07-05 | 1997-10-31 | Ciba Geigy Ag | New herbicides |
| WO1996011516A1 (fr) | 1994-10-05 | 1996-04-18 | Massachusetts Institute Of Technology | Microcavites resonnantes pourvues de guides d'ondes dielectriques periodiques monodimensionnels |
| GB9422708D0 (en) * | 1994-11-10 | 1995-01-04 | Zeneca Ltd | Herbicides |
| GB9422667D0 (en) | 1994-11-10 | 1995-01-04 | Zeneca Ltd | Herbicides |
| US5675017A (en) | 1995-06-07 | 1997-10-07 | Monsanto Company | Herbicidal substituted 3-aryl-pyrazoles |
| DE19532048A1 (de) | 1995-08-31 | 1997-03-06 | Basf Ag | Substituierte Benzthiazole als Pflanzenschutzmittel |
| JP3047180B1 (ja) | 1999-03-30 | 2000-05-29 | 株式会社桜木組 | 風力発電機 |
-
1997
- 1997-01-12 UA UA99074139A patent/UA53679C2/uk unknown
- 1997-12-01 JP JP52723798A patent/JP2001506641A/ja not_active Withdrawn
- 1997-12-01 KR KR1019990705383A patent/KR20000057600A/ko not_active Application Discontinuation
- 1997-12-01 BR BR9713947-5A patent/BR9713947A/pt unknown
- 1997-12-01 CA CA002275611A patent/CA2275611A1/fr not_active Abandoned
- 1997-12-01 PL PL97334253A patent/PL334253A1/xx unknown
- 1997-12-01 CN CNB97181435XA patent/CN1145626C/zh not_active Expired - Fee Related
- 1997-12-01 AT AT97954346T patent/ATE275146T1/de not_active IP Right Cessation
- 1997-12-01 US US09/331,065 patent/US6232470B1/en not_active Expired - Fee Related
- 1997-12-01 EA EA199900513A patent/EA002350B1/ru not_active IP Right Cessation
- 1997-12-01 IL IL13046997A patent/IL130469A/en not_active IP Right Cessation
- 1997-12-01 SK SK778-99A patent/SK77899A3/sk unknown
- 1997-12-01 WO PCT/EP1997/006715 patent/WO1998027090A2/fr not_active Application Discontinuation
- 1997-12-01 EP EP97954346A patent/EP0944623B1/fr not_active Expired - Lifetime
- 1997-12-01 HU HU0000543A patent/HUP0000543A3/hu not_active Application Discontinuation
- 1997-12-01 NZ NZ336368A patent/NZ336368A/xx unknown
- 1997-12-01 DE DE59711889T patent/DE59711889D1/de not_active Expired - Lifetime
- 1997-12-01 GE GEAP19974913A patent/GEP20022859B/en unknown
- 1997-12-01 TR TR1999/01351T patent/TR199901351T2/xx unknown
- 1997-12-01 AU AU58536/98A patent/AU744339B2/en not_active Ceased
- 1997-12-15 ZA ZA9711235A patent/ZA9711235B/xx unknown
- 1997-12-16 AR ARP970105913A patent/AR008943A1/es unknown
- 1997-12-16 TW TW086118977A patent/TW474916B/zh not_active IP Right Cessation
-
1999
- 1999-06-15 NO NO19992924A patent/NO313880B1/no unknown
- 1999-07-05 BG BG103554A patent/BG63873B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL334253A1 (en) | 2000-02-14 |
| EA002350B1 (ru) | 2002-04-25 |
| CN1244865A (zh) | 2000-02-16 |
| EA199900513A1 (ru) | 2000-02-28 |
| TW474916B (en) | 2002-02-01 |
| JP2001506641A (ja) | 2001-05-22 |
| ZA9711235B (en) | 1999-06-15 |
| IL130469A0 (en) | 2000-06-01 |
| SK77899A3 (en) | 1999-11-08 |
| NO992924L (no) | 1999-08-13 |
| WO1998027090A2 (fr) | 1998-06-25 |
| NZ336368A (en) | 2000-12-22 |
| KR20000057600A (ko) | 2000-09-25 |
| ATE275146T1 (de) | 2004-09-15 |
| GEP20022859B (en) | 2002-12-25 |
| US6232470B1 (en) | 2001-05-15 |
| DE59711889D1 (de) | 2004-10-07 |
| HUP0000543A2 (hu) | 2000-06-28 |
| EP0944623B1 (fr) | 2004-09-01 |
| BR9713947A (pt) | 2000-10-24 |
| IL130469A (en) | 2001-10-31 |
| NO992924D0 (no) | 1999-06-15 |
| TR199901351T2 (xx) | 1999-09-21 |
| CA2275611A1 (fr) | 1998-06-25 |
| CN1145626C (zh) | 2004-04-14 |
| EP0944623A2 (fr) | 1999-09-29 |
| UA53679C2 (uk) | 2003-02-17 |
| AR008943A1 (es) | 2000-02-23 |
| BG103554A (en) | 2000-06-30 |
| HUP0000543A3 (en) | 2002-01-28 |
| AU744339B2 (en) | 2002-02-21 |
| BG63873B1 (bg) | 2003-04-30 |
| AU5853698A (en) | 1998-07-15 |
| WO1998027090A3 (fr) | 1998-09-17 |
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