HU204506B - Process for producing phenyl-hydrazine derivatives - Google Patents
Process for producing phenyl-hydrazine derivatives Download PDFInfo
- Publication number
- HU204506B HU204506B HU90750A HU75090A HU204506B HU 204506 B HU204506 B HU 204506B HU 90750 A HU90750 A HU 90750A HU 75090 A HU75090 A HU 75090A HU 204506 B HU204506 B HU 204506B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- halogen
- phenylhydrazine
- preparation
- optionally
- Prior art date
Links
- 150000004031 phenylhydrazines Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229940067157 phenylhydrazine Drugs 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims 1
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical class NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 claims 1
- 101100274581 Caenorhabditis elegans chc-1 gene Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- -1 phenylhydrazine compound Chemical class 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 4
- GUNBDVRVSUIARG-UHFFFAOYSA-N 2-chloro-3-[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazinyl]propanenitrile Chemical compound ClC(CNNC1=C(C=C(C=C1Cl)C(F)(F)F)Cl)C#N GUNBDVRVSUIARG-UHFFFAOYSA-N 0.000 description 1
- WVCYGEWTHSGGET-UHFFFAOYSA-N 2-chloro-3-[2-[2-chloro-4-(trifluoromethyl)phenyl]hydrazinyl]propanenitrile Chemical compound FC(F)(F)C1=CC=C(NNCC(Cl)C#N)C(Cl)=C1 WVCYGEWTHSGGET-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-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
- KSESZRGARIEOFC-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1Cl KSESZRGARIEOFC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
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- 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
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- 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
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (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)
Description
A leírás terjedelme: 8 oldal (ezen belül 5 lap ábra)
HU 204506 Β szerinti eljárásban 1 mól (II) általános képletű fenil-hidrazin-származékra - a képletben R4R8 jelentése a már megadott - számítva általában 1,03,0 mól, előnyösen 1,0-1,5 mól) (Dl) általános képletű 2-halogén-akrilnitril-szánnazékot- a képletben Hal jelentése a már megadott - illetve 1,0-10,0 mól segédanyagot alkalmazunk.
A terméket ismert módon, például a szerves oldószer eltávolításával, a tennék vízben történő kicsapásával, leszívatásával és szárításával dolgozzuk fel és izoláljuk.
1. példa (1) képletű vegyület előállítása
20,0 g (0,095 mól) 2-klőr-4-(trifluor-metil)-fenilhidrazint 150 ml metanolban oldunk és 20 mg etiléndiamin-tetraecetsav-dinátrium-sóval elegyítünk. A kapott oldatot felforraljuk és cseppenként 32 ml (0,38 mól) 2-klőr-akril-nitrillel elegyítjük. A kapott reakcióelegyet 10 órán át keverés közben forraljuk, lehűtjük és a reakcióelegyet vákuumban 13,332 Pa nyomáson szárazra pároljuk. A visszamaradó anyag 27,9 g (98,6%) N’-(2’-klőr-2’-ciano-etil)-2-klór-4-(trifluormetil)-fenil-hidrazin. Op.: 56-57 °C.
2. példa (2) képletű vegyület előállítása
4,9 g (0,02 mól) 2,6-diklór-4-(trifluor-metil)-feniIhidrazint 40 ml metanolban oldunk, majd 5 mg etiléndiamin-teíraeceísav-dináíriumsőval elegyítünk. A reakcióelegyet felforraljuk, és cseppenként 5,25 g (0,06 mól) 2-klör-akril-nitrillel elegyítjük. A kapott reakcióelegyet 4 órán át forraljuk, lehűtjük, és vákuumban 0,133 mbar nyomáson szárazra pároljuk. Visszamaradó anyagként 5,0 g (75%) N’-(2’-klór-2’-cianoétil)-2,6-diklór-4-(trifluor-metil)-fenil-hidrazint kapunk olajként, a vegyület NMR spektrumát az 5/5 rajzlapon mutatjuk be.
Claims (2)
- SZABADALMI IGÉNYPONTEljárás az (I) általános képletű fenil-hidrazin-származékok - a képletben R4 jelentése halogénatom,Rő jelentése halogénatom vagy halogén-metil-csoport,R8 jelentése hidrogénatom vagy halogénatom, és Z jelentése (a) általános képletű csoport - a képletben Hal jelentése halogénatom előállítására, azzal jellemezve, hogy a (H) általános képletű fenilhidrazin-származékot - a képletben R4, R6 és R8 jelentése a tárgyi körben megadott - a (Hl) általános képletű 2-halogén-akril-nitrillel - a képletben Hal jelentése halogénatom reagáltatjuk, adott esetben hígítószer, valamint adott esetben reakciót elősegítő anyag jelenlétében.A találmány tárgya eljárás fenil-hidrazin-szánnazékok előállítására. Ezek a vegyületek közbenső termékként alkalmazhatók herbicid hatású helyettesített 5-aminol-fenil-pírazol-szánnazékok előállításánál.A 2701316 számú német szövetségi közíár- 5 saságbeli közrebocsátási irat 5-amino-pírazol-származékok előállítását ismerteti, az eljárás szerint a közbenső termékeket, azaz a találmányunk szerinti (I) általános képletnek megfelelő fenil-hidrazin-származékokat azonban nem izolálják. Emellett a példákban is csak 10 helyettesítetlen fenil-hidrazín-szánnazékok előállítását mutatják be, speciálisan helyettesített fenil-hidrazinokről nem beszélnek.A találmányunk feladatául tűztök ki ezzel szemben, hogy speciálisan helyettesített (I) általános képletű fe- 15 nil-hidrazin-származékokat állítsunk elő; az ezekből a vegyületekből előállítható végtermékek (5-amíno-I-fenil-pirazol-szánnazékok) különösen értékes, rendkívül hatásos tulajdonságokkal rendelkeznek (200 891 számú magyar szabadalmi leírás).A találmány szerint előállított vegyűleteket az (I) általános képlet ábrázolja. Ebben R4 jelentése halogénaíom,R6 jelentése halogénatom vagy halogén-metil-csoport,R8 jelentése hidrogénatom vagy halogénatom, és Z jelentése (a) általános képletű csoport- aképletben Hal jelentése halogénatom.Az új (I) általános képletű fenil-hidrazin-származékokat úgy állítjuk elő, hogy a (H) általános képletű fenil-hidrazin-szánnazékot- a képletben R4, Rff és R8 jelentése a tárgyi körben megadott - a (M) általános képletű 2-halogén-akrií-nitrillel - a képletben Hal jelentése halogénatomreagáltatjuk, adott esetben hígítószer, valamint adott esetben reakciót elősegítő anyag jelenlétében.Ha kiindulási anyagként például 2-kIór-akriInitriIt és 2,6-diklőr-4-(trifluor-mefil)-feniI-hidrazint alkalmazunk, akkor a herbicid hatású 5-amino-l-fenil-pirazolszánnazékok az (I) általános képletű vegyületek előálIításátkövetően cüdizálással állíthatók elő az a) reak- 40 ciővázlatnak megfelelően.A találmány szerinti eljárásban inért szerves oldószereket alkalmazunk. Előnyösen hígítószerek az alkoholok - így a metanol, az etanol, a propanol, a butanol és az etilénglikol továbbá az etilénglikol-monometil- 45 és -etil-éter.A találmány szerinti eljárásban a reakcióban alkalmazott segédanyagok szerves vagy szervetlen savak. Előnyösen kénsavat vagy ecetsavat alkalmazunk, adott esetben pufferanyag, így például nátrium-acetát jelen- 50 létében.A találmány szerinti eljárásban a reakcióhőmérséklet megadott határok között változhat. Általában -30 °C és +50 °C, előnyösen -20 °C és +20 °C közötti hőmérsékleten dolgozunk. 55HU 204 506 Β Int. Cl.5: C 07 C 255/66R4R6-/0\-NH-NH2R8 (II ) ch2=cCNHal (III )HU 204506 Β Int. Cl.5: C07 C 255/66 f3cCH2~CHCl — CN (1 ) .CN-ch2-chvHal (a.)HU 204 506 Β Int. Cl.5: C 07 C 255/66a) reakcíóvázlatNH-NH2 ch2=c^CNCl —HCI (bázis)HU 204506 Β IntCl.5: C 07 C 255/66Cl .F3C NH - NH - CH2 - CHC1 - CN α
- (2)HU 204 506 Β Int. CL5: C 07 C 255/66 y/r..- regcc · rry .'Cfp.ZtZ.’Fecs”-•JVH93ÍHI-\ ^?·Γ8Ε.* ” .x*‘ Γ9.5 9.0 B.5 Θ.-0 7.5 7.0 6.5 . 6.0 5.5 5.0 4.S 4.0 3.5 3.0 2.5 2.0 J.5 i.O .5 0.0PPM
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Application Number | Priority Date | Filing Date | Title |
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DE19843402308 DE3402308A1 (de) | 1984-01-24 | 1984-01-24 | Herbizide mittel auf basis von pyrazolderivaten |
Publications (2)
Publication Number | Publication Date |
---|---|
HU900750D0 HU900750D0 (en) | 1990-04-28 |
HU204506B true HU204506B (en) | 1992-01-28 |
Family
ID=6225745
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU90750A HU204506B (en) | 1984-01-24 | 1985-01-23 | Process for producing phenyl-hydrazine derivatives |
HU85264A HU200891B (en) | 1984-01-24 | 1985-01-23 | Herbicide composition containing pyrazol derivatives as active components and process for producing these compounds |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU85264A HU200891B (en) | 1984-01-24 | 1985-01-23 | Herbicide composition containing pyrazol derivatives as active components and process for producing these compounds |
Country Status (20)
Country | Link |
---|---|
US (2) | US4614533A (hu) |
EP (1) | EP0154115B1 (hu) |
JP (2) | JPH075565B2 (hu) |
KR (1) | KR910000043B1 (hu) |
AR (1) | AR242565A1 (hu) |
AT (1) | ATE38128T1 (hu) |
AU (1) | AU571634B2 (hu) |
BR (1) | BR8500297A (hu) |
CA (1) | CA1245223A (hu) |
DD (2) | DD243281A5 (hu) |
DE (2) | DE3402308A1 (hu) |
DK (1) | DK171863B1 (hu) |
ES (6) | ES8601903A1 (hu) |
HU (2) | HU204506B (hu) |
IE (1) | IE850153L (hu) |
IL (1) | IL74115A (hu) |
NZ (1) | NZ210890A (hu) |
PH (1) | PH21813A (hu) |
TR (1) | TR22399A (hu) |
ZA (1) | ZA85537B (hu) |
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DE3539844A1 (de) * | 1985-11-09 | 1987-05-14 | Bayer Ag | Substituierte 5-amino-1-aryl-pyrazole |
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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 |
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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 |
US5262382A (en) * | 1991-10-03 | 1993-11-16 | Fmc Corporation | Herbicidal 1-pyridylpyrazole compounds |
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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 |
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US5707934A (en) * | 1995-04-28 | 1998-01-13 | Rhone-Poulenc Inc. | Plant growth regulation using 3-cyano-1-phenylpyrazoles such as fipronil |
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US6136983A (en) * | 1995-06-05 | 2000-10-24 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
US6060502A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
US6060495A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
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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 |
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TR21379A (tr) * | 1980-02-26 | 1984-05-02 | May & Baker Ltd | N-fenilpirazol t*revleri |
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 |
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 |
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 |
KR840000504A (ko) * | 1981-07-17 | 1984-02-22 | 원본미기재 | N- 페닐피라졸 유도체의 제조방법 |
MA19540A1 (fr) * | 1981-07-17 | 1983-04-01 | May & Baker Ltd | Derives du n-phenylpyrazole |
KR840000505A (ko) * | 1981-07-17 | 1984-02-22 | 원본미기재 | N- 페닐피라졸유도체의 제조방법 |
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 |
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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 EP EP85100295A patent/EP0154115B1/de not_active Expired
- 1985-01-14 DE DE8585100295T patent/DE3565756D1/de not_active Expired
- 1985-01-14 AT AT85100295T patent/ATE38128T1/de not_active IP Right Cessation
- 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 NZ NZ210890A patent/NZ210890A/en unknown
- 1985-01-22 DD DD85287314A patent/DD243281A5/de unknown
- 1985-01-22 TR TR2954A patent/TR22399A/xx unknown
- 1985-01-22 JP JP60008573A patent/JPH075565B2/ja not_active Expired - Lifetime
- 1985-01-22 CA CA000472597A patent/CA1245223A/en not_active Expired
- 1985-01-22 DD DD85272695A patent/DD233925A5/de 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 BR BR8500297A patent/BR8500297A/pt unknown
- 1985-01-23 ZA ZA85537A patent/ZA85537B/xx unknown
- 1985-01-23 ES ES539782A patent/ES8601902A1/es not_active Expired
- 1985-01-23 HU HU90750A patent/HU204506B/hu unknown
- 1985-01-23 ES ES539786A patent/ES539786A0/es active Granted
- 1985-01-23 IE IE850153A patent/IE850153L/xx unknown
- 1985-01-23 ES ES539785A patent/ES8601905A1/es not_active Expired
- 1985-01-23 HU HU85264A patent/HU200891B/hu unknown
- 1985-01-23 PH PH31760A patent/PH21813A/en unknown
- 1985-01-23 ES ES539784A patent/ES8601904A1/es not_active Expired
- 1985-01-23 ES ES539781A patent/ES8601901A1/es not_active Expired
- 1985-01-23 DK DK030985A patent/DK171863B1/da not_active IP Right Cessation
-
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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Legal Events
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DFA9 | Temporary prot. cancelled due to abandonment |