HU204506B - Process for producing phenyl-hydrazine derivatives - Google Patents

Process for producing phenyl-hydrazine derivatives Download PDF

Info

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
Application number
HU90750A
Other languages
English (en)
Other versions
HU900750D0 (en
Inventor
Otto Schallner
Reinhold Gehring
Erich Klauke
Joerg Stetter
Heinz-Juergen Wroblowsky
Robert R Schmidt
Hans-Joachim Santel
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of HU900750D0 publication Critical patent/HU900750D0/hu
Publication of HU204506B publication Critical patent/HU204506B/hu

Links

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)
  • 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)

  1. SZABADALMI IGÉNYPONT
    Eljárás 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. 55
    HU 204 506 Β Int. Cl.5: C 07 C 255/66
    R4
    R6-/0\-NH-NH2
    R8 (II ) ch2=c
    CN
    Hal (III )
    HU 204506 Β Int. Cl.5: C07 C 255/66 f3c
    CH2~CHCl — CN (1 ) .CN
    -ch2-chv
    Hal (a.)
    HU 204 506 Β Int. Cl.5: C 07 C 255/66
    a) reakcíóvázlat
    NH-NH2 ch2=c^
    CN
    Cl —HCI (bázis)
    HU 204506 Β IntCl.5: C 07 C 255/66
    Cl .
    F3C NH - NH - CH2 - CHC1 - CN α
  2. (2)
    HU 204 506 Β Int. CL5: C 07 C 255/66 y
    /
    r..- regcc · rry .'Cfp.Zt
    Z.’Fecs”
    -•JVH93ÍHI
    -\ ^?·Γ8Ε.* ” .x*‘ Γ
    9.5 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 0.0
    PPM
HU90750A 1984-01-24 1985-01-23 Process for producing phenyl-hydrazine derivatives HU204506B (en)

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 (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)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
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
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
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
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
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
US5262382A (en) * 1991-10-03 1993-11-16 Fmc Corporation Herbicidal 1-pyridylpyrazole compounds
US5167691A (en) * 1991-10-03 1992-12-01 Fmc Corporation Herbicidal 5-amino-1-phenyl pyrazole 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
CA2146852C (en) * 1992-10-12 2005-03-15 Gabriele Dorfmeister New substituted pyrazole derivatives, processes for their preparation and their use as herbicides
US5707934A (en) * 1995-04-28 1998-01-13 Rhone-Poulenc Inc. Plant growth regulation using 3-cyano-1-phenylpyrazoles such as fipronil
US5585329A (en) * 1995-04-28 1996-12-17 Rhone-Poulenc Inc. Plant growth promotion using 3-cyano-1-phenylpyrazoles such as fipronil
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
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
DE69715769T2 (de) * 1996-11-04 2003-05-28 Bayer Cropscience S.A., Lyon 1-Polyarylpyrazole als Pestizide
US6069157A (en) * 1997-11-25 2000-05-30 Pfizer Inc. Parasiticidal compounds
CO5060426A1 (es) * 1997-03-10 2001-07-30 Rhone Poulenc Agrochimie 1-aril-3-imidiopirazoles plaguicidas
ZA981776B (en) 1997-03-10 1998-09-03 Rhone Poulenc Agrochimie Pesticidal 1-arylpyrazoles
US7966078B2 (en) 1999-02-01 2011-06-21 Steven Hoffberg Network media appliance system and method
WO2000046229A1 (en) 1999-02-02 2000-08-10 Monsanto Technology Llc Production of phosphonopyrazoles
WO2005030128A2 (en) * 2003-09-23 2005-04-07 Merck & Co., Inc. Pyrazole modulators of metabotropic glutamate receptors
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)

* Cited by examiner, † Cited by third party
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
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
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

Also Published As

Publication number Publication date
TR22399A (tr) 1987-03-25
ES539784A0 (es) 1985-11-16
DK30985D0 (da) 1985-01-23
US4614533A (en) 1986-09-30
ZA85537B (en) 1985-09-25
BR8500297A (pt) 1985-09-03
DD233925A5 (de) 1986-03-19
EP0154115B1 (de) 1988-10-26
CA1245223A (en) 1988-11-22
US5104439A (en) 1992-04-14
NZ210890A (en) 1988-04-29
PH21813A (en) 1988-03-04
ES539785A0 (es) 1985-11-16
ES8601904A1 (es) 1985-11-16
DE3402308A1 (de) 1985-08-01
DK30985A (da) 1985-07-25
JPH03115257A (ja) 1991-05-16
ES8601906A1 (es) 1985-11-16
IL74115A (en) 1989-10-31
IE850153L (en) 1985-07-24
ATE38128T1 (de) 1988-11-15
ES539786A0 (es) 1985-11-16
DD243281A5 (de) 1987-02-25
IL74115A0 (en) 1985-04-30
ES539782A0 (es) 1985-11-16
HU900750D0 (en) 1990-04-28
JPH075536B2 (ja) 1995-01-25
ES539783A0 (es) 1985-11-16
ES8601902A1 (es) 1985-11-16
AU571634B2 (en) 1988-04-21
ES539781A0 (es) 1985-11-16
ES8601905A1 (es) 1985-11-16
JPH075565B2 (ja) 1995-01-25
AR242565A1 (es) 1993-04-30
DK171863B1 (da) 1997-07-21
HUT37548A (en) 1986-01-23
AU3776385A (en) 1985-08-01
HU200891B (en) 1990-09-28
ES8601903A1 (es) 1985-11-16
KR910000043B1 (ko) 1991-01-19
JPS60174756A (ja) 1985-09-09
KR850005415A (ko) 1985-08-26
DE3565756D1 (en) 1988-12-01
ES8601901A1 (es) 1985-11-16
EP0154115A1 (de) 1985-09-11

Similar Documents

Publication Publication Date Title
HU204506B (en) Process for producing phenyl-hydrazine derivatives
SU1223842A3 (ru) Способ получени производных бензофенонгидразонов
JPH05247039A (ja) 新規テトラオキソ−ジアザビシクロ−（３，３，１）−ノナンおよびその製法
US4171365A (en) Antiviral aryloxyalkylpyrazoles
GB2053210A (en) Substituted 3-arylpyrazoles and 5-arylisoxazoles
HU177482B (en) Process for preparing new uracyl derivatives
CA1116620A (en) PROCESS FOR PRODUCING N-SUBSTITUTED.alpha.-KETOCARBOXYLIC AMIDES
US4968808A (en) Process for the preparation of nitroethene derivatives
US4125721A (en) Process for the production of 2,4-diamino-5-(3&#39;,4&#39;,5&#39;-trimethoxybenzyl)-pyrimidine
US5663365A (en) Process for the preparation of pyrazolones
US5565575A (en) Method for the production of 5-cyclohexylmethylhydantoin derivatives
CA1137482A (en) Process for the production of 5-aminoisoxazoles
JPS6399063A (ja) ４−アミノ−１，２，４−トリアゾリン−５−チオン系化合物の製造方法
US4354976A (en) Process for the preparation of azidobenzal compounds
Bolis et al. v-Triazolines. Part 8. 1-Aryl-4-alkyl-and-aryl-thiomethyl-5-amino-v-triazolines: synthesis and reactions with bases
Tret'yakov et al. Synthesis of vicinal aminoiodo-and (acetylamino) iodo-l-alkylpyrazoles
US6562979B1 (en) Process for the preparation of substituted benzisothiazole compounds
JP3808538B2 (ja) １ｈ−１，２，４−トリアゾール−５−イル酢酸類および、その製造法
JP2767080B2 (ja) ２‐（イミダゾリル‐４’）ベンズイミダゾール化合物とその合成方法
Cohen‐Fernandes et al. On the nitro group transfer from 2‐nitro‐4, 5, 6, 7‐tetrachloro‐2H‐benzotriazole and 2‐nitro‐2H‐phenanthro [9, 10‐d] triazole to secondary amines
US4551525A (en) Process for preparing N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
KR930006198B1 (ko) 신규 α-클로로케톤 유도체 및 그 제조법
JPH0528708B2 (hu)
US4567260A (en) Synthesis of 5-deazariboflavine
JPS5811434B2 (ja) ホルミル酢酸エステルのアシルヒドラゾンの製造法

Legal Events

Date Code Title Description
DFA9 Temporary prot. cancelled due to abandonment