KR850005415A - 치환된 5-아미노-1-페닐-피라졸의 제조방법 - Google Patents
치환된 5-아미노-1-페닐-피라졸의 제조방법 Download PDFInfo
- Publication number
- KR850005415A KR850005415A KR1019850000411A KR850000411A KR850005415A KR 850005415 A KR850005415 A KR 850005415A KR 1019850000411 A KR1019850000411 A KR 1019850000411A KR 850000411 A KR850000411 A KR 850000411A KR 850005415 A KR850005415 A KR 850005415A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- hydrogen
- amino
- optionally
- halogenoalkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical class NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 title claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- 239000001257 hydrogen Substances 0.000 claims 35
- -1 chlorosulfonyl group Chemical group 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 238000006243 chemical reaction Methods 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 239000003085 diluting agent Substances 0.000 claims 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 239000007858 starting material Substances 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- 150000008360 acrylonitriles Chemical class 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 2
- 229940067157 phenylhydrazine Drugs 0.000 claims 2
- 150000004031 phenylhydrazines Chemical class 0.000 claims 2
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims 2
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims 1
- 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 claims 1
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 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 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 claims 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 claims 1
- CWNBIZNFVWOUFW-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbaldehyde Chemical compound NC1=NNC=C1C=O CWNBIZNFVWOUFW-UHFFFAOYSA-N 0.000 claims 1
- FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical compound NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 claims 1
- DXPOQSLSMWZYSB-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-sulfonyl chloride Chemical compound NC=1NN=CC=1S(Cl)(=O)=O DXPOQSLSMWZYSB-UHFFFAOYSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 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 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005998 bromoethyl group Chemical group 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- 210000000078 claw Anatomy 0.000 claims 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 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
- 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 claims 1
- CRSKJTCLPSICOZ-UHFFFAOYSA-N n-[4-acetyl-2-(2,3,4,5,6-pentafluorophenyl)pyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C(C(C)=O)C=NN1C1=C(F)C(F)=C(F)C(F)=C1F CRSKJTCLPSICOZ-UHFFFAOYSA-N 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000006000 trichloroethyl group Chemical group 0.000 claims 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 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 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
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- 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
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- a) 일반식(Ⅱ)의 페닐하이드라진을 일반식(Ⅲ)의 아크릴로니트릴 유도체와 반응시키거나, R1이 수소일 경우에는 일반식(Ⅲa)의 2-할로게노아크릴로니트릴과 반응시키거나, 일반식(Ⅲb)의 2,3-디할로게노프로피오니트릴과 반응시키고, 이 반응은 제1단계로, 경우에 따라 희석제 존재하, 경우에 따라 반응보조제 존재하에서 수행하여 일반식(Ⅳ)의 페닐하이드라진 유도체를 수득한 다음, 제2단계로 생성물을 경우에 따라 희석제 존재하, 경우에 따라 산-결합제 존재하에서 폐환 반응시키거나 일반식(Ⅳ)의 중간체를 분리시키지 않고 경우에 따라 희석제 존재식에서 일단계 반응으로 직접 폐환시켜 일반식(Ⅰa)의 5-아미노-피라졸을 수득하며, 또는 b) 공정(a)에서 수득할 수 있는 일반식(Ⅰa)의 5-아미노-피리졸을 경우에 따라 희석제 존재하, 경우에 따라 산-결합제 존재하에서 일반식(Ⅴ)의 아실화제 또는 알킬화제 또는 일반식(Ⅵ)의 이소(티오) 시아네아트와 반응시켜 질소에서 알킬화 또는 아실화된 일반식(Ⅰb)의 5-아미노-피리졸을 수득하거나, c) 공정(a) 또는 (b)에 의하여 수득할 수 있는 4-위치에 비치환된 일반식(Ⅰc)의 5-아미노-피리졸을 경우에 따라 희석제 존재하, 경우에 따라 촉매 또는 반응 보조제 존재하에서 일반식(Ⅶ)의 친전자성 시약을 사용하거나 다른 통상의 친전자성 시약을 사용하여 4-위치에서 치환시키거나, d) 공정(c)에 의하여 수득할 수 있는 일반식(Ⅰd)의 4-클로로설포닐-5-아미노-피리졸을 경우에 따라 희석제 존재하, 경우에 따라 산-결합제 존재하에서 일일반식(Ⅷ)의 아민을 사용하거나 일반식(Ⅸ)의 알칼리 금속의 불소화물을 사용하여 4-위치의 클로로 설포닐 그룹에서 치환시키거나, e) 공정(c) 또는 (f)에 의하여 수득할 수 있는 일반식(Ⅰe)의 4-아실-5-아미노-피리졸을 경우에 따라 희석제 존재하, 경위에 따라 산-결합제 존재하에서 일반식(Ⅹ)의 하이드록실아민 유도체 또는 그의 하이드로-염(염산염(HCl염)과 같은 할로겐화 수소 부가염)과 반응시키거나, f) 일반식(XI)의 4-시아노-5-아미노-피리졸을 포름산 및 레니(Raney) 니켈과 반응시켜 상응하는 일반식(Ⅰf)의 5-아미노-4-포르밀-피리졸을 수득함을 특징으로 하여, 일반식(Ⅰ')의 치환된 5-아미노-1-페닐-피리졸을 제조하는 방법.상기 식에서, R1은 수소, 니트로소, 니트로, 할로겐, 알킬, 할로게노알킬, 임의로 치환된 아릴 또는 라디칼중의 하나이고, R2는 수소 또는 라디칼-이고, R3는 R2와 독립적으로 수소 또는 라이칼디거나 또는 알킬이고, R4및 R6는 각각 독립적으로 시아노, 니트로, 할로겐, 알킬, 알콕시, 알콕시카보닐, 할로게노알킬, 할로게노알콕시 또는 라디칼-S(O)n-R13이고, R5, R7및 R8은 각각 R4및 R6와는 독립적으로 시아노, 니트로,할로겐, 알킬, 알콕시, 알콕시카보닐, 할로게노알킬, 할로게노알콕시 또는 라디카-S(O)n-R13이거나 수소이고, R9은 수소, 하이드록실, 할로겐, 아미노, 알킬아미노, 디알킬아미노, 알킬, 할로게노알킬 또는 임의로 치환된 아릴이고, R10은 수소, 알킬 또는 임의로 치환된 아릴이고, R11은 수소, 알킬, 할로게노알킬, 알케닐, 알키닐 또는 아르알킬이고, R12는 수소, 알킬, 알케닐, 알키닐, 할로게노알킬, 알콕시알킬, 알킬티오알킬, 임의로 치환된 사이클로알킬, 임의로 치환된 아릴, 알콕시, 알킬티오, 임의로 치환된 아릴옥시, 임의로 치환된 아릴티오, 알킬아미노, 디알킬아미노, 또는 임의로 치환된 아릴아미노이고, R13은 알킬, 할로게노알킬, 아미노, 알킬아미노 또는 디알킬아미노이고, x는 산소 또는 황이고, n은 정수 0,1 또는 2이고, 단, R1이 수소, 메틸 또는 임의로 치환된 페닐일 경우에는, R4및 R6가 동시에 니트로그룹일 수 없으며, A는 할로겐이드록시 또는 알콕시이고, Hal 및 Hal'는 할로겐, 특히 염소 브롬이고, Z는 라디칼(여기에서, Hal 및 Hal'는 동일 또는 상이한 할로겐원자하다)중의 하나이고, R14는 알킬 또는 라디칼이고, A' 및 E는 전자-유인성 이탈그룹이고, R15는 알킬 또는 임의로 치환된 아릴이고, R3'는 수소를 제외한 상기의 R3와 같고, R1'는 할로겐, 니트로소,니트로 알킬 포르밀, 알카노일, 아로일, 하이드록시설포닐 또는 클로로설포닐이고, R16및 R17은 각각 독립적으로 수소 또는 알킬이고, Me는 알칼리 금속의 양이온이다.
- 제1항의 공정(a)에 있어서, 2-클로로아크릴로니트릴 및 2,6-디클로로-4-트리플루오로메틸-페닐하이드라진을 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1항의 공정(b)에 있어서, 5-아미노-1-(2,4,6-트리클로로페닐)-피라졸 및 프로피오닐 클로라이드를 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1항의 공정(c)에 있어서, 5-프로피온아미도-1-(2,3,4-트리클로로페닐)-피라졸 및 질산을 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1항에 공정(d)에 있어서, 5-아세토아미도-4-클로로설포닐-1-(2,4,6-트리클로로페닐)-피라졸 및 디에틸아민을 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1항의 공정(e)에 있어서, 5-아세토아미도-4-아세틸-1-(펜타플루오로페닐)-피라졸 및 0-메틸-하이드록실아민 하이드로클로라이드를 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1항의 공정(f)에 있어서, 5-아미노-4-시아노-1-(2,3,4-트리클로로페닐)-피라졸 및 포름산을 출발물질로서 사용하여 반응을 수행하는 방법.
- 제1 내지 7항중 어느 하나에 있어서, R1이 수소, 니트로소,니트로, 할로겐, C6까지의 직쇄 또는 측쇄 알킬, 동일 또는 상이한 할로겐원자를 9개까지 갖는 C6까지의 직쇄 또는 측쇄 할로게노알킬 또는 동일 또는 상이한 치환체(예:할로겐, 니트로, 각 경우 C4까지의 알킬, 알콕시 또는 할로게노알킬)에 의하여 임의로 일- 또는 디-치환된 페닐이거나, 라디칼OR"중의 하나이고, R2가 수소 또는 라디칼이고, R3가 R2와 독립적으로 수소 또는 라디칼이거나 또는 C4까지의 직쇄 또는 측쇄 알킬이고, R4및 R6가 각각 독립적으로 시아노, 니트로, 할로겐 또는 각 경우 C4까지의 직쇄 또는 측쇄알킬, 알콕시 또는 알콕시카보닐 이거나, 각 경우 동일 또는 상이한 할로겐원자를 9개까지 갖는 C4까지의 직쇄 또는 출쇄 할로게노알킬 또는 할로게노알콕시이거나, 라디칼-S(O)n-R13이고, R5, R7및 R8은 각각, R4및 R5와 독립적으로 R4,R6와 동일하게 정의되거나, 수소이고, R9가 수소, 하이드록실, 불소, 염소, 아미노 또는 각경우, 각 알킬부가 C4까지이고, 할로게노 알킬의 경우에는 동일 또는 상이한 할로겐원자를 9개까지의 갖는 직쇄또는 측쇄의 알킬아미노, 디알킬아미노, 알킬 또는 할로게노알킬이거나, 동일 또는 상이한 치환체(예:할로겐 각 경우 C4까지이고, 할로게노 알킬의 경우에는 동일 또는 상이한 할로겐 원자를 9개까지 갖는 측쇄 또는 측쇄의 알킬, 알콕시 또는 할로게노알킬)에 의하여 임의로 일-또는 디-치환된 페닐이고, R10이 수소, C4까지의 직쇄 또는 측쇄알킬 또는 R9의 경우와 동일하게 동일 또는 상이한 치환체에 의하여 임의로 일- 또는 다-치환된 페닐이고, R11이 수소, 동일 또는 상이한 할로겐원자를 6개까지 갖는 C4까지의 할로게노알킬, C8까지의 직쇄 또는 측쇄의 알킬, 알케닐 또는 알케닐 또는 알킬부가 C4까지인 직쇄 또는 측쇄 페닐알킬이고, R12가 수소, C1내지 C12의 직쇄 또는 측쇄 알킬 또는 각 경우, 각 알킬부가 C4까지이고 할로게노알킬의 경우에는 동일 또는 상이한 할로겐 원자를 9개까지 갖는 직쇄 또는 측쇄의 알케닐, 알키닐, 알콕시알킬, 알킬티오알킬, 알콕시, 알킬티오, 알킬아미노, 디알킬아미노 또는 할로게노알킬이거나, 동일 또는 상이한 치환체(예:할로겐, 저급 알킬 또는 저급 할로게노알킬)에 의하여 임의로 일- 또는 다-치환된 C3내지 C7사이클로아킬이거나, 각 경우, 동일 또는 상이한 치환체(예:R9의 경우와 동일)에 의하여 임의로 일- 또는 디-치환된 페닐, 페녹시, 페닐티오 또는 페닐아미노이고, R13이 아미노 또는 각 경우, 각 알킬부가 C4까지이고 할로게노알킬의 경우에는 동일 또는 상이한 할로겐원자를 9개까지 갖는 직쇄 또는 측쇄의 알킬, 알킬아미노, 디알킬아미노 또는 할로게노알킬이고, x가 산소 또는 황이고, n이 0,1 또는 2의 정수이며, 단, R1이 수소, 메틸 또는 임의로 치환된 페닐일 경우에는 R4및 R6가 동시에 니트로 그룹일 수 없는 일반식(Ⅰ')의 치환된 5-아미노-1-페닐-피라졸을 제조하는 방법.
- 제1 내지 7항중 어느 하나에 있어서, R1이 수소, 니트로소, 니트로, 불소, 염소, 브롬, 메틸, 에틸, n- 또는 i-프로필, n-, i-, 2급-또는 3급-부틸, 트리플루오로메틸 또는 동일 또는 상이한 치환체(예:불소, 염소, 브롬, 니트로, 메틸, 에틸, 메톡시 및 트리플루오로메틸)에 의하여 임의로 일-내지 삼-치환된 페닐이거나, 라디칼중의 하나이고, R2가 수소 또는 라디칼이고, R3가 R2와 독립적으로 수소 또는 라디칼이거나, 메틸, 에틸, n-또는 i-프로필 또는 n-, i-, 2급-또는 3급-부틸이고, R4및 R6가 각각 독립적으로 시아노, 니트로, 불소, 염소, 브롬, 요오드, 메틸, 에틸, n-또는 i-프로필, n-, i-,2급-또는 3급-부틸, 메톡시, 에톡시, 메톡시, 카보니르 에톡시카보닐, 트리플루오로메틸, 트리클로로메틸, 디클로로플루오로메틸, 디플루오로클로로메틸, 클로로메틸, 디클로로메틸, 디클루오로메틸, 펜타플루오로에틸, 테트라플루오로에틸, 트리플루오로클로로에틸, 트리플루오로에틸, 디플루오로디클로로에틸, 트리플루우로디클로로에틸, 펜타클로로에틸, 트리플루오로메톡시, 트리클로로메톡시, 디클로로플루오로메톡시, 디플루오로클로로메톡시, 클로로메톡시, 디클로로메톡시, 디플루오로메톡시, 펜타플루오로에톡시, 테트라플루오로에톡시, 트리플루오로클로로에톡시, 트리풀루오로에톡시, 디플루오로디클로로에톡시, 트리플루오로디클로오에톡시, 펜타클로로에톡시 또는 라디칼-S(O)n-R12이고, R5,R7및 R8이 각각, R4및 R6와 독립적으로 R4및 R6와 동일하게 정의되거나, 수소이고, R9가 수소, 하이드록실, 불소, 염소, 브롬, 아미노, 메틸아미노, 디메틸아미노, 에틸아미노, 디에틸아미노, 디이소프로필아미노, 디-n-부틸아미노, 메틸, 에틸, 디클로로플루오로메틸 또는 트리플루오로메틸이거나, 동일 또는 상이한 치환체(예:메틸, 메톡시, 트리플루오로메틸 또는 염소)에 의하여 임의로 일- 내지 삼-치환된 페닐이고, R10이 수소, 메틸, 에틸, n-또는 i-프로필이거나; 동일 또는 상이한 치환체(예:메틸, 메톡시, 트리플루오로메틸 또는 염소)에 의하여 임의로 일- 내지 삼-치환된 페닐이고, R11이 수소, 메틸, 에틸, n-또는 i-프로필, n-, i-, 2급 또는 3급-부틸, 알킬, 부테닐, 프로파르길, 벤질, 클로로에틸 또는 브로모에틸이고, R12가 수소, 메틸, 에틸, n-또는 i-프로필, 운데실, 비닐, 알릴, 프로파르길, 부테닐, 메톡시메틸, 에톡시메틸, 메톡시에틸, 에톡시에틸, 메틸티오메틸, 메톡시, 에톡시, 메틸티오, 에틸티오, 메틸아미노, 에틸아미노, 디메틸아미노, 디에틸아미노, 트리플루오로메틸, 트리클로로에틸, 디클로로플루오로에틸, 디플루오로클로로에틸, 클로로메틸, 요오드메틸, 브로모메틸, 디클로로메틸, 1-클로로에틸, 2-클로로에틸, 2-브로모에틸, 클로로프로필 또는 헵타플루오로-n-프로필이거나, 동일 또는 상이한 치환체(예:불소, 염소, 브롬, 메틸 또는 트리플루오로메틸)에 의하여 임의로 일- 내지 삼-치환된 사이클로펜틸, 사이클로헥실 또는 사이클로프로필이거나, 각 경우, 동일 또는 상이한 치환체(예:메틸, 메톡시, 염소 또는 트리플루오로메틸)에 의하여 임의로 일- 내지 삼-치환된 페닐, 페녹시, 페닐티오, 또는 페닐아미노이고, R13이 아미노, 메틸아미노, 에틸아미노, 디메틸아미노, 디에틸아미노, 플루오로디클로로메틸, 디플루오로메틸, 테트라플루오로에틸, 트리플루오로클로로에틸, 트리플루오로메틸, 메틸 또는 에틸이고, x가 산소 또는 황이고, n이 0,1 또는 2의 정수이며, 단, R1이 수소, 메틸 또는 임의로 치환된 페닐일 경우에는 R4및 R6가 동시에 니트로 그룹일 수 없는 일반식(Ⅰ')의 치환된 5-아미노-1-페닐-피라졸을 제조하는 방법.
- 일반식(Ⅱ)의 페닐하이드라진을 경우에 따라 희석제 존재하, 경우에 따라 반응 보조제 존재하에서 일반식(Ⅲ)의 아크릴로니트릴 유도체, 일반식(Ⅲa)의 2-할로게노아크릴로니트릴 또는 일반식(Ⅲb)의 2,3-디할로게노프로피오니트릴과 반응시킴을 특징으로 하여, 제1항에서 정의된 일반식(Ⅳ)의 페닐하이드라진 유도체를 제조하는 방법.상기 식에서, R1은 수소, 니트로소, 니트로, 할로겐, 알킬, 할로게노알킬, 임의로 치환된 아릴 또는 라디칼중의 하나이고, R4및 R6는 각각 독립적으로 시아노, 니트로, 할로겐, 알킬, 알콕시, 알콕시카보닐, 할로게노알킬, 할로게노알콕시 또는 라디칼-S(O)n-R13이고, R5, R7및 R4및 R6와는 독립적으로 시아노, 니트로, 할로겐, 알킬, 알콕시, 카보닐, 할로게노알콕시 또는 라디칼-S(O)n-R13이거나 수소이고, R9은 수소 하이드록실, 할로겐, 아미노, 알킬아미노, 디알킬아미노, 알킬, 할로게노알킬 또는 임의로 치환된 아릴이고, R10은 수소, 알킬 또는 임의로 치환된 아릴이고, R11은 수소, 알킬, 할로게노알킬, 알케일, 알키닐 또는 아르알킬이고, A는 할로겐, 하이드록실 또는 알콕시이고, Hal 및 Hal'는 할로겐, 특히 염소 또는 브롬이고, R13은 알킬, 할로게노알킬, 아미노, 알킬아미노 또는 디알킬아미노이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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|---|---|---|---|
| DEP3402308.9 | 1984-01-24 | ||
| DE19843402308 DE3402308A1 (de) | 1984-01-24 | 1984-01-24 | Herbizide mittel auf basis von pyrazolderivaten |
| DE????P3402308.9 | 1984-01-24 |
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| KR910000043B1 KR910000043B1 (ko) | 1991-01-19 |
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| KR1019850000411A KR910000043B1 (ko) | 1984-01-24 | 1985-01-23 | 치환된 5-아미노-1-페닐-파라졸의 제조방법 |
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| DE (2) | DE3402308A1 (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| DE3543034A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-perfluoracylamino-4-nitro-1-aryl-pyrazol-salze |
| 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 |
| US6372774B1 (en) | 1985-12-20 | 2002-04-16 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | 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 |
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-
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 TR TR2954A patent/TR22399A/xx unknown
- 1985-01-22 CA CA000472597A patent/CA1245223A/en not_active Expired
- 1985-01-22 NZ NZ210890A patent/NZ210890A/en unknown
- 1985-01-22 DD DD85272695A patent/DD233925A5/de unknown
- 1985-01-22 JP JP60008573A patent/JPH075565B2/ja not_active Expired - Lifetime
- 1985-01-22 DD DD85287314A patent/DD243281A5/de unknown
- 1985-01-23 IE IE850153A patent/IE850153L/xx unknown
- 1985-01-23 ES ES539785A patent/ES8601905A1/es not_active Expired
- 1985-01-23 ES ES539783A patent/ES8601903A1/es not_active Expired
- 1985-01-23 ZA ZA85537A patent/ZA85537B/xx unknown
- 1985-01-23 ES ES539782A patent/ES539782A0/es active Granted
- 1985-01-23 ES ES539784A patent/ES8601904A1/es not_active Expired
- 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 ES539786A patent/ES8601906A1/es not_active Expired
- 1985-01-23 ES ES539781A patent/ES539781A0/es active Granted
- 1985-01-23 HU HU85264A patent/HU200891B/hu unknown
- 1985-01-23 BR BR8500297A patent/BR8500297A/pt unknown
- 1985-01-23 KR KR1019850000411A patent/KR910000043B1/ko not_active IP Right Cessation
- 1985-01-23 HU HU90750A patent/HU204506B/hu unknown
-
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
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