DD243281A5 - Verfahren zur herstellung von substituierten 5-amino-1-phenyl-pyrazolen - Google Patents
Verfahren zur herstellung von substituierten 5-amino-1-phenyl-pyrazolen Download PDFInfo
- Publication number
- DD243281A5 DD243281A5 DD85287314A DD28731485A DD243281A5 DD 243281 A5 DD243281 A5 DD 243281A5 DD 85287314 A DD85287314 A DD 85287314A DD 28731485 A DD28731485 A DD 28731485A DD 243281 A5 DD243281 A5 DD 243281A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- amino
- ocf
- alkyl
- optionally
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 33
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 7
- 235000019253 formic acid Nutrition 0.000 claims abstract description 7
- FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical class NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 1281
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- -1 iso (thio) cyanates Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 239000003085 diluting agent Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 238000002955 isolation Methods 0.000 claims description 8
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002443 hydroxylamines Chemical class 0.000 claims description 6
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- DXPOQSLSMWZYSB-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-sulfonyl chloride Chemical class NC=1NN=CC=1S(Cl)(=O)=O DXPOQSLSMWZYSB-UHFFFAOYSA-N 0.000 claims description 5
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 241000251730 Chondrichthyes Species 0.000 claims description 4
- 150000008360 acrylonitriles Chemical class 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- CWNBIZNFVWOUFW-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbaldehyde Chemical class NC1=NNC=C1C=O CWNBIZNFVWOUFW-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 235000021190 leftovers Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 52
- 150000001875 compounds Chemical class 0.000 abstract description 13
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical class NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 abstract description 8
- 230000002363 herbicidal effect Effects 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000007858 starting material Substances 0.000 description 21
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000002484 inorganic compounds Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- DWMGFASJKTZERP-UHFFFAOYSA-N 2-(2,4,6-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(Cl)C=C(Cl)C=C1Cl DWMGFASJKTZERP-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FYOWOHMZNWQLFG-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYOWOHMZNWQLFG-UHFFFAOYSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DLEGTWJGAAHTCH-UHFFFAOYSA-N n-[2-(2,3,4-trichlorophenyl)pyrazol-3-yl]propanamide Chemical compound CCC(=O)NC1=CC=NN1C1=CC=C(Cl)C(Cl)=C1Cl DLEGTWJGAAHTCH-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IYBKJASNAMGBOI-UHFFFAOYSA-N (2,3,4-trichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C(Cl)=C1Cl IYBKJASNAMGBOI-UHFFFAOYSA-N 0.000 description 1
- MZWTXWPYEFIRGT-UHFFFAOYSA-N (3-cyano-6-ethoxyhex-5-en-3-yl)phosphonic acid Chemical compound C(C)OC=CCC(C#N)(P(=O)(O)O)CC MZWTXWPYEFIRGT-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RJJDLPQZNANQDQ-UHFFFAOYSA-N 2,3-dichloropropanenitrile Chemical compound ClCC(Cl)C#N RJJDLPQZNANQDQ-UHFFFAOYSA-N 0.000 description 1
- SXOFMEWDEKEVJU-UHFFFAOYSA-N 2,5-diphenylpyrazol-3-amine Chemical compound NC1=CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 SXOFMEWDEKEVJU-UHFFFAOYSA-N 0.000 description 1
- BPYUUMRTYIQQGV-UHFFFAOYSA-N 2-(2,3,4-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=C(Cl)C(Cl)=C1Cl BPYUUMRTYIQQGV-UHFFFAOYSA-N 0.000 description 1
- WKUCXENZDGYYOM-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)-4-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(=CC=2)[N+]([O-])=O)[N+]([O-])=O)N=C1 WKUCXENZDGYYOM-UHFFFAOYSA-N 0.000 description 1
- YABJDORUHODXDB-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)-4-methylpyrazol-3-amine Chemical compound NC1=C(C)C=NN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YABJDORUHODXDB-UHFFFAOYSA-N 0.000 description 1
- JBLVUZURDPBLMW-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)-4-phenylpyrazol-3-amine Chemical compound NC1=C(C=2C=CC=CC=2)C=NN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O JBLVUZURDPBLMW-UHFFFAOYSA-N 0.000 description 1
- NXJCLNYWBFNGKR-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NXJCLNYWBFNGKR-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OVCCLTZJLDZBSP-UHFFFAOYSA-N 3-amino-5-propanoyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound C(#N)C=1C(=NN(C=1C(CC)=O)C1=C(C=C(C=C1Cl)Cl)Cl)N OVCCLTZJLDZBSP-UHFFFAOYSA-N 0.000 description 1
- XPGJXYAYXZDMBB-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,4-dinitrophenyl)pyrazol-3-amine Chemical compound NC1=C(C=2C=CC(Cl)=CC=2)C=NN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XPGJXYAYXZDMBB-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- AUKPYJFVFDSWPM-UHFFFAOYSA-N 4-diethoxyphosphoryl-2-(2,3,4-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=C(P(=O)(OCC)OCC)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl AUKPYJFVFDSWPM-UHFFFAOYSA-N 0.000 description 1
- XAMSFYGTOZNACI-UHFFFAOYSA-N 5-(2,4,6-trichlorophenyl)-1h-pyrazole Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C1=CC=NN1 XAMSFYGTOZNACI-UHFFFAOYSA-N 0.000 description 1
- ORPJRZZDHCBULV-UHFFFAOYSA-N 5-acetamido-1-(2,4,6-trichlorophenyl)pyrazole-4-sulfonyl chloride Chemical compound CC(=O)NC1=C(S(Cl)(=O)=O)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl ORPJRZZDHCBULV-UHFFFAOYSA-N 0.000 description 1
- DBFMKRVPJIOMHQ-UHFFFAOYSA-N 5-amino-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl DBFMKRVPJIOMHQ-UHFFFAOYSA-N 0.000 description 1
- YWJIGWCXSGRUNU-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethoxy)phenyl]pyrazole-4-carbaldehyde Chemical compound NC1=C(C=O)C=NN1C1=CC=C(OC(F)(F)F)C=C1Cl YWJIGWCXSGRUNU-UHFFFAOYSA-N 0.000 description 1
- ZKMBFVLHXFTPMY-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethoxy)phenyl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=C(OC(F)(F)F)C=C1Cl ZKMBFVLHXFTPMY-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000005333 aroyloxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SYWNRXZVUSASEL-UHFFFAOYSA-N n-[2-(2,4,6-trinitrophenyl)pyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=CC=NN1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SYWNRXZVUSASEL-UHFFFAOYSA-N 0.000 description 1
- OVNIHRPCROGWFT-UHFFFAOYSA-N n-[4-chloro-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]propanamide Chemical compound CCC(=O)NC1=C(Cl)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl OVNIHRPCROGWFT-UHFFFAOYSA-N 0.000 description 1
- BSFMLPIUXAUQQC-UHFFFAOYSA-N n-[4-nitro-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]propanamide Chemical compound CCC(=O)NC1=C([N+]([O-])=O)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl BSFMLPIUXAUQQC-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic 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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843402308 DE3402308A1 (de) | 1984-01-24 | 1984-01-24 | Herbizide mittel auf basis von pyrazolderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD243281A5 true DD243281A5 (de) | 1987-02-25 |
Family
ID=6225745
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85272695A DD233925A5 (de) | 1984-01-24 | 1985-01-22 | Herbizide mittel |
| DD85287314A DD243281A5 (de) | 1984-01-24 | 1985-01-22 | Verfahren zur herstellung von substituierten 5-amino-1-phenyl-pyrazolen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85272695A DD233925A5 (de) | 1984-01-24 | 1985-01-22 | Herbizide mittel |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4614533A (tr) |
| EP (1) | EP0154115B1 (tr) |
| JP (2) | JPH075565B2 (tr) |
| KR (1) | KR910000043B1 (tr) |
| AR (1) | AR242565A1 (tr) |
| AT (1) | ATE38128T1 (tr) |
| AU (1) | AU571634B2 (tr) |
| BR (1) | BR8500297A (tr) |
| CA (1) | CA1245223A (tr) |
| DD (2) | DD233925A5 (tr) |
| DE (2) | DE3402308A1 (tr) |
| DK (1) | DK171863B1 (tr) |
| ES (6) | ES8601902A1 (tr) |
| HU (2) | HU204506B (tr) |
| IE (1) | IE850153L (tr) |
| IL (1) | IL74115A (tr) |
| NZ (1) | NZ210890A (tr) |
| PH (1) | PH21813A (tr) |
| TR (1) | TR22399A (tr) |
| ZA (1) | ZA85537B (tr) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3503609A1 (de) * | 1985-02-02 | 1986-08-07 | Bayer Ag, 5090 Leverkusen | 5-sulfonamido-1-aryl-pyrazole |
| US4752326A (en) * | 1985-05-15 | 1988-06-21 | Hokko Chemical Industry Co., Ltd. | 1-arylpyrazoles, composition containing them, and herbicidal method of using them |
| DE3602728A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
| DE3520331A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | 1-aryl-5-alkoximinoalkylamino-pyrazole |
| DE3538731A1 (de) * | 1985-10-31 | 1987-05-07 | Bayer Ag | 1-aryl-4-nitro-pyrazole |
| DE3539844A1 (de) * | 1985-11-09 | 1987-05-14 | Bayer Ag | Substituierte 5-amino-1-aryl-pyrazole |
| DE3617977A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-dichloracetamido-4-nitro-1-aryl-pyrazole |
| DE3543035A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-fluoracylamino-4-nitro-1-aryl-pyrazole |
| DE3543034A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-perfluoracylamino-4-nitro-1-aryl-pyrazol-salze |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US6372774B1 (en) | 1985-12-20 | 2002-04-16 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| DE3600287A1 (de) | 1986-01-08 | 1987-07-16 | Bayer Ag | 1-arylpyrazole |
| DE3600950A1 (de) * | 1986-01-15 | 1987-07-16 | Bayer Ag | 5-acylamido-1-aryl-pyrazole |
| DE3603291A1 (de) * | 1986-02-04 | 1987-08-06 | Bayer Ag | 5-amino-1-phenyl-pyrazole |
| DE3606476A1 (de) * | 1986-02-28 | 1987-09-03 | Bayer Ag | 1-arylpyrazole |
| DE3609423A1 (de) * | 1986-03-20 | 1987-10-01 | Bayer Ag | Schaedlingsbekaempfungsmittel auf basis von 1-aryl-4-trifluormethyl-5-aminopyrazolen |
| DE3609542A1 (de) * | 1986-03-21 | 1987-10-01 | Bayer Ag | 5-acylamino-pyrazol-derivate |
| DE3612940A1 (de) * | 1986-04-17 | 1987-10-22 | Bayer Ag | Verfahren zur herstellung von 1-aryl-5-aminopyrazolen |
| DE3617554A1 (de) * | 1986-05-24 | 1987-11-26 | Bayer Ag | 5-oxy(thio)-pyrazol-derivate |
| DE3631003A1 (de) * | 1986-09-12 | 1988-03-24 | Bayer Ag | Verfahren zur herstellung von 4-substituierten 1-aryl-5-amino-pyrazolen |
| DE3637710A1 (de) * | 1986-11-05 | 1988-05-11 | Bayer Ag | 5-acylamino-pyrazol-derivate |
| DE3719733A1 (de) * | 1987-06-12 | 1989-01-05 | Bayer Ag | Substituierte 5-ethylamino-1-arylpyrazole |
| DE3721868A1 (de) * | 1987-07-02 | 1989-01-12 | Bayer Ag | 1-arylpyrazole |
| DE3725661A1 (de) * | 1987-08-03 | 1989-02-23 | Bayer Ag | 1-arylpyrazole |
| DE3726919A1 (de) * | 1987-08-13 | 1989-02-23 | Bayer Ag | 1-arylpyrazole |
| DE3742612A1 (de) * | 1987-12-16 | 1989-06-29 | Bayer Ag | Verfahren zur herstellung von 4-substituierten 3-methyl-1-aryl-5-amino-pyrazolen |
| DE3742822A1 (de) * | 1987-12-17 | 1989-07-13 | Bayer Ag | Verfahren zur herstellung von 5-amino-l-phenyl-4-nitro-pyrazolen |
| DE3742819A1 (de) * | 1987-12-17 | 1989-07-13 | Bayer Ag | Verfahren zur herstellung von 5-amino-1-phenyl-4-nitro-pyrazolen |
| GB8929101D0 (en) * | 1989-12-22 | 1990-02-28 | May & Baker Ltd | New mixtures |
| US5167691A (en) * | 1991-10-03 | 1992-12-01 | Fmc Corporation | Herbicidal 5-amino-1-phenyl pyrazole compounds |
| US5262382A (en) * | 1991-10-03 | 1993-11-16 | Fmc Corporation | Herbicidal 1-pyridylpyrazole compounds |
| DE4137872A1 (de) * | 1991-11-13 | 1993-05-19 | Schering Ag | Neue substituierte pyrazolylpyrazole, ihre herstellung sowie zwischenprodukte zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
| US8352400B2 (en) | 1991-12-23 | 2013-01-08 | Hoffberg Steven M | Adaptive pattern recognition based controller apparatus and method and human-factored interface therefore |
| US10361802B1 (en) | 1999-02-01 | 2019-07-23 | Blanding Hovenweep, Llc | Adaptive pattern recognition based control system and method |
| SK281874B6 (sk) * | 1992-10-12 | 2001-08-06 | Hoechst Schering Agrevo Gmbh | Substituované pyrazolové deriváty, spôsob ich prípravy, medziprodukty tohto spôsobu a použitie týchto pyrazolových derivátov ako herbicídnych látok |
| US5585329A (en) * | 1995-04-28 | 1996-12-17 | Rhone-Poulenc Inc. | Plant growth promotion using 3-cyano-1-phenylpyrazoles such as fipronil |
| US5707934A (en) * | 1995-04-28 | 1998-01-13 | Rhone-Poulenc Inc. | Plant growth regulation using 3-cyano-1-phenylpyrazoles such as fipronil |
| US6136983A (en) * | 1995-06-05 | 2000-10-24 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
| US6060495A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
| US6060502A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
| US5922885A (en) * | 1995-12-19 | 1999-07-13 | Rhone-Poulenc Inc. | Pesticidal 1-arylpyrazole derivatives |
| US5817688A (en) * | 1995-12-19 | 1998-10-06 | Rhone-Poulenc Inc. | Pesticidal 1-arylpyrazole derivatives |
| EP0839810B1 (en) | 1996-11-04 | 2002-09-25 | Aventis Cropscience S.A. | Pesticidal 1-polyarylpyrazoles |
| US6069157A (en) * | 1997-11-25 | 2000-05-30 | Pfizer Inc. | Parasiticidal compounds |
| ZA981776B (en) * | 1997-03-10 | 1998-09-03 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles |
| CO5060426A1 (es) * | 1997-03-10 | 2001-07-30 | Rhone Poulenc Agrochimie | 1-aril-3-imidiopirazoles plaguicidas |
| US7904187B2 (en) | 1999-02-01 | 2011-03-08 | Hoffberg Steven M | Internet appliance system and method |
| CN1348457A (zh) | 1999-02-02 | 2002-05-08 | 孟山都技术有限公司 | 膦酰基吡唑的生产 |
| JP2007506741A (ja) * | 2003-09-23 | 2007-03-22 | メルク エンド カムパニー インコーポレーテッド | 向代謝性グルタミン酸受容体のピラゾール系調節剤 |
| WO2005082917A1 (en) * | 2004-02-26 | 2005-09-09 | Bayer Cropscience S.A. | 4-phosphorylpyrazole derivatives for pesticidal use |
| US7983835B2 (en) | 2004-11-03 | 2011-07-19 | Lagassey Paul J | Modular intelligent transportation system |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3398158A (en) * | 1964-02-19 | 1968-08-20 | Warner Lambert Pharmaceutical | 1-phenyl-4-alkylamino-pyrazoles |
| IT1061812B (it) * | 1976-06-25 | 1983-04-30 | Montedison Spa | Processo per la preparazione di i fenil 3 ammino pirazoli |
| DE3010099A1 (de) * | 1980-02-25 | 1981-09-03 | BBC AG Brown, Boveri & Cie., Baden, Aargau | Elektronische schutzschaltung |
| DK155302B (da) * | 1980-02-26 | 1989-03-28 | May & Baker Ltd | N-phenylpyrazolderivater og herbicid med indhold deraf |
| EP0053698B1 (de) * | 1980-12-05 | 1985-01-09 | BASF Aktiengesellschaft | 5-Amino-1-phenylpyrazol-4-carbonsäureester, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung als Herbizide |
| EP0053678A1 (de) * | 1980-12-05 | 1982-06-16 | BASF Aktiengesellschaft | 5-Amino-1-phenyl-4-cyanpyrazole, diese enthaltende herbizide Mittel, Verfahren zu ihrer Herstellung und ihre Anwendung als Herbizide |
| DE3045903A1 (de) * | 1980-12-05 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | 5-amino-1-phenylpyrazol-4-carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
| JPS57139068A (en) * | 1981-02-20 | 1982-08-27 | Fbc Ltd | Herbicidal heterocyclic compound |
| JPS57167972A (en) * | 1981-04-08 | 1982-10-16 | Otsuka Chem Co Ltd | Chloroacetylaminopyrazole derivative, its preparation, and herbicide comprising it |
| KR840000505A (ko) * | 1981-07-17 | 1984-02-22 | 원본미기재 | N- 페닐피라졸유도체의 제조방법 |
| MA19540A1 (fr) * | 1981-07-17 | 1983-04-01 | May & Baker Ltd | Derives du n-phenylpyrazole |
| SU1410859A3 (ru) * | 1981-07-17 | 1988-07-15 | Мэй Энд Бейкер Лимитед (Фирма) | Способ борьбы с сорн ками |
| DE3129429A1 (de) * | 1981-07-25 | 1983-02-10 | Basf Ag, 6700 Ludwigshafen | 5-amino-1-phenyl-pyrazol-4-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| MA19840A1 (fr) * | 1982-07-15 | 1984-04-01 | May & Baker Ltd | Alcoylamino n-phenyl pyrazole et n-phenyl pyrazole lactames herbicides . |
| DE3538731A1 (de) * | 1985-10-31 | 1987-05-07 | Bayer Ag | 1-aryl-4-nitro-pyrazole |
| DE3603291A1 (de) * | 1986-02-04 | 1987-08-06 | Bayer Ag | 5-amino-1-phenyl-pyrazole |
-
1984
- 1984-01-24 DE DE19843402308 patent/DE3402308A1/de not_active Withdrawn
-
1985
- 1985-01-10 US US06/690,347 patent/US4614533A/en not_active Expired - Lifetime
- 1985-01-14 AT AT85100295T patent/ATE38128T1/de not_active IP Right Cessation
- 1985-01-14 EP EP85100295A patent/EP0154115B1/de not_active Expired
- 1985-01-14 DE DE8585100295T patent/DE3565756D1/de not_active Expired
- 1985-01-17 AU AU37763/85A patent/AU571634B2/en not_active Ceased
- 1985-01-21 IL IL74115A patent/IL74115A/xx unknown
- 1985-01-21 AR AR85299300A patent/AR242565A1/es active
- 1985-01-22 DD DD85272695A patent/DD233925A5/de unknown
- 1985-01-22 TR TR2954A patent/TR22399A/tr unknown
- 1985-01-22 NZ NZ210890A patent/NZ210890A/en unknown
- 1985-01-22 CA CA000472597A patent/CA1245223A/en not_active Expired
- 1985-01-22 DD DD85287314A patent/DD243281A5/de unknown
- 1985-01-22 JP JP60008573A patent/JPH075565B2/ja not_active Expired - Lifetime
- 1985-01-23 HU HU90750A patent/HU204506B/hu unknown
- 1985-01-23 ES ES539782A patent/ES8601902A1/es not_active Expired
- 1985-01-23 ES ES539781A patent/ES539781A0/es active Granted
- 1985-01-23 IE IE850153A patent/IE850153L/xx unknown
- 1985-01-23 ES ES539786A patent/ES8601906A1/es not_active Expired
- 1985-01-23 HU HU85264A patent/HU200891B/hu unknown
- 1985-01-23 BR BR8500297A patent/BR8500297A/pt unknown
- 1985-01-23 DK DK030985A patent/DK171863B1/da not_active IP Right Cessation
- 1985-01-23 PH PH31760A patent/PH21813A/en unknown
- 1985-01-23 ES ES539785A patent/ES539785A0/es active Granted
- 1985-01-23 ZA ZA85537A patent/ZA85537B/xx unknown
- 1985-01-23 KR KR1019850000411A patent/KR910000043B1/ko not_active IP Right Cessation
- 1985-01-23 ES ES539783A patent/ES8601903A1/es not_active Expired
- 1985-01-23 ES ES539784A patent/ES539784A0/es active Granted
-
1990
- 1990-08-20 US US07/569,493 patent/US5104439A/en not_active Expired - Lifetime
- 1990-09-05 JP JP2235485A patent/JPH075536B2/ja not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD243281A5 (de) | Verfahren zur herstellung von substituierten 5-amino-1-phenyl-pyrazolen | |
| DD253172A5 (de) | Herbizide mittel | |
| DE3520328A1 (de) | 5-amino-4-heterocyclyl-1-pyridyl-pyrazole | |
| EP0248315A2 (de) | 5-Acylamino-pyrazol-Derivate | |
| DE3520330A1 (de) | 5-amino-1-pyridyl-pyrazole | |
| DD260431A5 (de) | Herbizide und pflanzenwuchsregulierende mittel | |
| DE3810382A1 (de) | 5-amino-1-phenylpyrazole, verfahren sowie 5-halogen-1-phenylpyrazole als zwischenprodukte zu deren herstellung und ihre verwendung als herbizide | |
| EP0303153A2 (de) | 1-Arylpyrazole | |
| EP0173821B1 (de) | Substituierte 5-Amino-1-phenylpyrazole | |
| DD242165A5 (de) | Herbizide mittel | |
| EP0260521A1 (de) | Verfahren zur Herstellung von 4-substituierten 1-Aryl-5-amino-pyrazolen | |
| DD253937A5 (de) | Herbizide mittel | |
| DE3447211A1 (de) | Verfahren zur herstellung von substituierten phenylhydrazinen | |
| EP0222253B1 (de) | Substituierte 5-Amino-1-aryl-pyrazole | |
| DE3423582A1 (de) | Substituierte 5-acylamino-1-phenylpyrazole | |
| EP0320764A2 (de) | Verfahren zur Herstellung von 5-Amino-1-Phenyl-4-nitro-pyrazolen | |
| EP0245646B1 (de) | Verfahren zur Herstellung von 1-Aryl-5-amino-pyrazolen | |
| DD256640A5 (de) | Herbizide und pflanzenwuchsregulierende mittel | |
| DE3612940A1 (de) | Verfahren zur herstellung von 1-aryl-5-aminopyrazolen | |
| DD258558A5 (de) | 1-aryl-5-hydrazino-pyrazole | |
| DE3237479A1 (de) | Verfahren zur herstellung von substituierten tetrahydropyrimidinonderivaten | |
| EP0320750B1 (de) | Verfahren zur Herstellung von 4-substituierten 3-Methyl-1-aryl-5-amino-pyrazolen | |
| EP0151312B1 (de) | N'-Acylhydrazin-N-thiocarbonsäure-O-carbamoylmethylester | |
| EP0276721A1 (de) | 2-Cyan-2-oximino-acetamide | |
| DE3503609A1 (de) | 5-sulfonamido-1-aryl-pyrazole |