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AR029165A1 - NITRILE COMPOUNDS OF REPLACED ARILMALONIC ACID AND PROCESS FOR PREPARATION - Google Patents

NITRILE COMPOUNDS OF REPLACED ARILMALONIC ACID AND PROCESS FOR PREPARATION

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Publication number
AR029165A1
AR029165A1 ARP000102931A ARP000102931A AR029165A1 AR 029165 A1 AR029165 A1 AR 029165A1 AR P000102931 A ARP000102931 A AR P000102931A AR P000102931 A ARP000102931 A AR P000102931A AR 029165 A1 AR029165 A1 AR 029165A1
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Argentina
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carbon atoms
alkyl
alkoxy
atoms
carbon
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ARP000102931A
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Spanish (es)
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Syngenta Participations Ag
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    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Proceso para la preparacion de derivados de 3-hidroxi-4-aril-5-oxopirazolina sustituidos de la formula (1) en donde R0 es, cada uno independientemente de cualquier otro, halogeno, alquilo de 1 a 6 átomos de carbono, alquenilo de 2 a 6 átomos de carbono alquinilo de 2 a 6 átomos de carbono, haloalquilo de 1 a 6 átomos de carbono, cianoalquilo de 1 a 6 átomos de carbono, haloalquenilo de 2 a 6 átomos de carbono, cianoalquenilo de 2 a 6 átomos de carbono, haloalquinilo de 2 a 6 átomos de carbono, cianoalquinilo de 2 a 6 átomos de carbono, hidroxilo, hidroxialquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono, nitro, amino, alquilamino de 1 a 6 átomos de carbono, di(alquilo de 1 a 6 átomos de carbono) amino, alquilcarbonilamino de 1 a 6 átomos de carbono, alquilsulfinilamino de 1 a 6 átomos de carbono, alquilaminosulfonilo de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono-alquinilo de 2 a 6 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono-alquinilo de 2 a 6 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono, ciano, carboxilo, fenilo o un anillo aromático que contiene uno o dos heteroátomos seleccionados a partir del grupo que consiste en nitrogeno, oxígeno y azufre en donde los dos ultimos anillos aromáticos pueden estar sustituidos por alquilo de 1 a 3 átomos de carbono, haloalquilo de 1 a 3 átomos de carbono, alcoxilo de 1 a 3 átomos de carbono, haloalcoxilo de 1 a 3 átomos de carbono, halogeno, ciano, o por nitro; o R0 junto con los sustituyentes adyacentes R1, R2, y R3 forma un puente de hidrocarburo de 3 a 6 átomos de carbono saturado o insaturado que puede estar interrumpido por uno o dos heteroátomos seleccionados a partir del grupo que consiste en nitrogeno, oxígeno, y azufre, y/o puede estar sustituido por alquilo de 1 a 4 átomos de carbono; R1, R2, y R3 son cada uno independientemente de los otros, hidrogeno, halogeno, alquilo de 1 a 6 átomos de carbono, alquenilo de 2 a 6 átomos de carbono, alquinilo de 2 a 6 átomos de carbono, cicloalquilo de 3 a 6 átomos de carbono, haloalquilo de 1 a 6 átomos de carbono, haloalquenilo de 2 a 6 átomos de carbono; alcoxicarbonilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, cianoalquenilo de 2 a 6 átomos de carbono, nitroalquenilo de 2 a 6 átomos de carbono, haloalquinilo de 2 a 6 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono-alquinilo de 2 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono-alquinilo de 2 a 6 átomos de carbono, cianoalquinilo de 2 a 6 átomos de carbono, nitroalquinilo de 2 a 6 átomos de carbono, halocicloalquilo de 3 a 6 átomos de carbono, hidroxialquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, tioalquilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, ciano, alquilcarbonilo de 1 a 4 átomos de carbono, alcoxicarbonilo de 1 a 6 átomos de carbono, hidroxilo, alcoxilo de 1 a 10 átomos de carbono, alqueniloxilo de 3 a 6 átomos de carbono, alquiniloxilo de 3 a 6 átomos de carbono, haloalcoxilo de 1 a 6 átomos de carbono, haloalqueniloxilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alcoxilo de 1 a 6 átomos de carbono, mercapto, tioalquilo de 1 a 6 átomos de carbono, halotioalquilo de 1 a 6 átomos de carbono, alquilsulfinilo de 1 a 6 átomos de carbono, alquilsulfonilo de 1 a 6 átomos de carbono nitro, amino, alquilamino de 1 a 6 átomos de carbono, di(alquilo de 1 a 6 átomos de carbono)amino, o fenoxilo, en donde el anillo de fenilo puede estar sustituido por alquilo de 1 a 3 átomos de carbono, haloalquilo de 1 a 3 átomos de carbono, alcoxilo de 1 a 3 átomos de carbono, haloalcoxilo de 1 a 3 átomos de carbono, halogeno, ciano, o por nitro; R2 también puede ser fenilo, naftilo, o un anillo aromático de 5 o 6 miembros que puede contener uno o dos heteroátomos seleccionados a partir del grupo que consiste en nitrogeno, oxígeno y azufre, en donde el anillo de fenilo, el sistema de anillo de naftilo y el anillo aromático de 5 o 6 miembros pueden estar sustituidos por halogeno, cicloalquilo de 3 a 8 átomos de carbono, hidroxilo, mercapto, amino, ciano, nitro, o por formilo; y/o el anillo de fenilo, el sistema de anillo de naftilo, y el anillo aromático de 5 o 6 miembros, pueden estar sustituidos por alquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono, hidroxialquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alcoxilo de 1 a 6 átomos de carbono; alquilcarbonilo de 1 a 6 átomos de carbono, tioalquilo de 1 a 6 átomos de carbono, alquilsulfinilo de 1 a 6 átomos de carbono, alquilsulfonilo de 1 a 6 átomos de carbono, monoalquilamino de 1 a 6 átomos de carbono, di(alquilo de 1 a 6 átomos de carbono) amino, alquilcarbonilamino de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono(alquilo de 1 a 6 átomos de carbono) amino, alquenilo de 2 a 6 átomos de carbono, alqueniloxilo de 3 a 6 átomos de carbono; hidroxialquenilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alqueniloxilo de 3 a 6 átomos de carbono, alquenilcarbonilo de 2 a 6 átomos de carbono, tioalquenilo de 2 a 6 átomos de carbono, alquenilsulfinilo de 2 a 6 átomos de carbono, alquenilsufonilo de 2 a 6 átomos de carbono, mono - o di-(alquenilo de 2 a 6 átomos de carbono) amino, alquilo de 1 a 6 átomos de carbono (alquenilo de 3 a 6 átomos de carbono) amino, alquenilcarbonilamino de 2 a 6 átomos de carbono, alquenilcarbonilo de 2 a 6 átomos de carbono (alquilo de 1 a 6 átomos de carbono) amino, alquinilo de 2 a 6 átomos de carbono, alquiniloxilo de 3 a 6 átomos de carbono, hidroxialquinilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquinilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquiniloxilo de 4 a 6 átomos de carbono, alquinilcarbonilo de 2 a 6 átomos de carbono, tioalquinilo de 2 a 6 átomos de carbono, alquilsulfonilo de 2 a 6 átomos de carbono, alquinilsulfonilo de 2 a 6 átomos de carbono, mono o di-(alquinilo de 3 a 6 átomos de carbono) amino, alquilo de 1 a 6 átomos de carbono (alquinilo de 3 a 6 átomos de carbono)amino, alquinilcarbonilamino de 2 a 6 átomos de carbono, o por alquinilcarbonilo de 2 a 6 átomos de carbono(alquilo de 1 a 6 átomos de carbono)amino; y/o el anillo de fenilo, el sistema de anillo de naftilo, y el anillo aromático de 5 o 6 miembros, pueden estar sustituido por alquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono, hidroxialquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquilo de 1 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alcoxilo de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono, tioalquilo de 1 a 6 átomos de carbono, alquilsulfinilo de 1 a 6 átomos de carbono, alquilsufonilo de 1 a 6 átomos de carbono, monoalquilamino de 1 a 6 átomos de carbono, di(alquilo de 1 a 6 átomos de carbono)amino, alquilcarbonilamino de 1 a 6 átomos de carbono, alquilcarbonilo de 1 a 6 átomos de carbono (alquilo de 1 a 6 átomos de carbono) amino, alquenilo de 2 a 6 átomos de carbono, alqueniloxilo de 3 a 6 átomos de carbono, hidroxialquenilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquenilo de 2 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alqueniloxilo de 3 a 6 átomos de carbono, alquenilcarbonilo de 2 a 6 átomos de carbono, tioalquenilo de 2 a 6 átomos de carbono, alquenilsulfinilo de 2 a 6 átomos de carbono, alquenilsulfonilo de 2 a 6 átomos de carbono, mono- o di-(alquenilo de 2 a 6 átomos de carbono) amino, alquilo de 1 a 6 átomos de carbono(alquenilo de 3 a 6 átomos de carbono) amino, alquenilcarbonilamino de 2 a 6 átomos de carbono, alquenilcarbonilo de 2 a 6 átomos de carbono (alquilo de 1 a 6 átomos de carbono) amino, alquinilo de 2 a 6 átomos de carbono, alquiniloxilo de 3 a 6 átomos de carbono, hidroxialquinilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquinilo de 3 a 6 átomos de carbono, alcoxilo de 1 a 6 átomos de carbono-alquiniloxilo de 4 a 6 átomos de carbono, alquinilcarbonilo de 2 a 6 átomos de carbono; tioalquinilo de 2 a 6 átomos de carbono, alquinilsulfinilo de 2 a 6 átomos de carbono, alquinilsulfonilo de 2 a 6 átomos de carbono, mono- o di(alquinilo de 3 a 6 átomos de carbono) amino, alquilo de 1 a 6 átomos de carbono (alquinilo de 3 a 6 átomos de carbono) amino, alquinilcarbonilamino de 2 a 6 átomos de carbono o por alquinilcarbonilo de 2 a 6 átomos de carbono (alquilo de 1 a 6 átomos de carbono)amino, sustituidos por halogeno; y/o el anillo de fenilo, el sistema de anillo de naftilo, y el anillo aromático de 5 a 6 miembros pueden estar sustituidos por un radical de la formula COOR50, CONR51, SO2NR53R54, o SO2OR55, en donde R50, R51, R52, R53, R54, R55 son cada uno independientemente de los otros, alquilo de 1 a 6 átomos de carbono, alquenilo de 2 a 6 átomos de carbono, o alquinilo de 3 a 6 átomos de carbono, sustituidos por halogeno, hidroxilo, alcoxilo, mercapto, amino, ciano, nitro, tioalquilo, alquilsulfinilo, o alquilsulfonilo; n es 0, 1 o 2; y R4, R5 y G son cada uno como se definen en la reivindicacion 1, cuyo proceso comprende hacer reaccionar un compuesto de la formula (2) en donde R0, R1, R2, R3 y n son como se definen anteriormente en la presente; R6 es R8R9N-; R7 es R10R11N- o R12O-; y R8, R9, R10, R11 y R12 son cada uno indepeProcess for the preparation of substituted 3-hydroxy-4-aryl-5-oxopyrazoline derivatives of the formula (1) wherein R0 is, each independently of any other, halogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms alkynyl of 2 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, cyanoalkyl of 1 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, cyanoalkenyl of 2 to 6 carbon atoms , haloalkynyl of 2 to 6 carbon atoms, cyanoalkynyl of 2 to 6 carbon atoms, hydroxyl, hydroxyalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, nitro, amino, alkylamino of 1 to 6 atoms of carbon, di (alkyl of 1 to 6 carbon atoms) amino, alkylcarbonylamino of 1 to 6 carbon atoms, alkylsulfinylamino of 1 to 6 carbon atoms, alkylaminosulfonyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms , alkylcarbonyl of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms-alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms-alkenyl from 2 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms-alkynyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms-alkynyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 atoms of carbon, cyano, carboxyl, phenyl or an aromatic ring containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur where the last two aromatic rings may be substituted by alkyl of 1 to 3 carbon atoms , haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro; or R0 together with the adjacent substituents R1, R2, and R3 forms a hydrocarbon bridge of 3 to 6 saturated or unsaturated carbon atoms that may be interrupted by one or two heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and / or may be substituted by alkyl of 1 to 4 carbon atoms; R1, R2, and R3 are each independently of the others, hydrogen, halogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms; alkoxycarbonyl of 1 to 6 carbon-alkenyl atoms of 2 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon-alkenyl atoms of 2 to 6 carbon atoms, cyanoalkenyl of 2 to 6 carbon atoms, nitroalkenyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms-alkynyl of 2 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms-alkynyl of 2 to 6 carbon atoms, cyanoalkynyl from 2 to 6 carbon atoms, nitroalkynyl of 2 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 atoms carbon, thioalkyl of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, cyano, alkylcarbonyl of 1 to 4 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, hydroxyl, alkoxy of 1 to 10 atoms of carbon, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 at 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, haloalkenyloxy of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkoxy of 1 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 atoms carbon, halothioalkyl of 1 to 6 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms nitro, amino, alkylamino of 1 to 6 carbon atoms, di (alkyl of 1 to 6 atoms carbon) amino, or phenoxy, wherein the phenyl ring may be substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon, halogen, cyano, or nitro atoms; R2 may also be phenyl, naphthyl, or a 5- or 6-membered aromatic ring that may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the ring system of naphthyl and the 5- or 6-membered aromatic ring may be substituted by halogen, cycloalkyl of 3 to 8 carbon atoms, hydroxyl, mercapto, amino, cyano, nitro, or formyl; and / or the phenyl ring, the naphthyl ring system, and the 5- or 6-membered aromatic ring, may be substituted by alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, hydroxyalkyl of 1 at 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkoxy of 1 to 6 carbon atoms; alkylcarbonyl of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, monoalkylamino of 1 to 6 carbon atoms, di (alkyl of 1 at 6 carbon atoms) amino, alkylcarbonylamino of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino, alkenyl of 2 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms; hydroxyalkenyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkenyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkenyloxy of 3 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, thioalkenyl of 2 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkenyl sulfonyl of 2 to 6 carbon atoms, mono- or di- (alkenyl of 2 to 6 carbon atoms) amino, alkyl of 1 to 6 carbon atoms (alkenyl of 3 to 6 carbon atoms) amino, alkenylcarbonylamino of 2 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino, alkynyl of 2 at 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, hydroxyalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms -alkynyloxy of 4 to 6 carbon atoms, alkynylcarbonyl of 2 to 6 carbon atoms, t ioalkynyl of 2 to 6 carbon atoms, alkylsulfonyl of 2 to 6 carbon atoms, alkylsulfonyl of 2 to 6 carbon atoms, mono or di- (alkynyl of 3 to 6 carbon atoms) amino, alkyl of 1 to 6 atoms of carbon (alkynyl of 3 to 6 carbon atoms) amino, alkynylcarbonylamino of 2 to 6 carbon atoms, or by alkynylcarbonyl of 2 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino; and / or the phenyl ring, the naphthyl ring system, and the 5- or 6-membered aromatic ring, may be substituted by alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, hydroxyalkyl of 1 at 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkoxy of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms , thioalkyl of 1 to 6 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkylsufonyl of 1 to 6 carbon atoms, monoalkylamino of 1 to 6 carbon atoms, di (alkyl of 1 to 6 carbon atoms) amino, alkylcarbonylamino of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino, alkenyl of 2 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, hydroxyalkenyl of 3 at 6 carbon atoms, alkoxy of 1 to 6 carbon-alkenyl atoms of 2 to 6 carbon atoms or, alkoxy of 1 to 6 carbon atoms-alkenyloxy of 3 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, thioalkenyl of 2 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkenylsulfonyl of 2 at 6 carbon atoms, mono- or di- (alkenyl of 2 to 6 carbon atoms) amino, alkyl of 1 to 6 carbon atoms (alkenyl of 3 to 6 carbon atoms) amino, alkenylcarbonylamino of 2 to 6 atoms of carbon, alkenylcarbonyl of 2 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino, alkynyl of 2 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, hydroxyalkynyl of 3 to 6 carbon atoms, alkoxy from 1 to 6 carbon-alkynyl atoms of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkynyloxy of 4 to 6 carbon atoms, alkynylcarbonyl of 2 to 6 carbon atoms; thioalkynyl of 2 to 6 carbon atoms, alkylsulfinyl of 2 to 6 carbon atoms, alkylsulfonyl of 2 to 6 carbon atoms, mono- or di (alkynyl of 3 to 6 carbon atoms) amino, alkyl of 1 to 6 atoms of carbon (alkynyl of 3 to 6 carbon atoms) amino, alkynylcarbonylamino of 2 to 6 carbon atoms or by alkynylcarbonyl of 2 to 6 carbon atoms (alkyl of 1 to 6 carbon atoms) amino, substituted by halogen; and / or the phenyl ring, the naphthyl ring system, and the 5- to 6-membered aromatic ring may be substituted by a radical of the formula COOR50, CONR51, SO2NR53R54, or SO2OR55, wherein R50, R51, R52, R53, R54, R55 are each independently of the others, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, or alkynyl of 3 to 6 carbon atoms, substituted by halogen, hydroxyl, alkoxy, mercapto , amino, cyano, nitro, thioalkyl, alkylsulfinyl, or alkylsulfonyl; n is 0, 1 or 2; and R4, R5 and G are each as defined in claim 1, whose process comprises reacting a compound of the formula (2) wherein R0, R1, R2, R3 and n are as defined hereinbefore; R6 is R8R9N-; R7 is R10R11N- or R12O-; and R8, R9, R10, R11 and R12 are each indepe

ARP000102931A 1999-06-16 2000-06-14 NITRILE COMPOUNDS OF REPLACED ARILMALONIC ACID AND PROCESS FOR PREPARATION AR029165A1 (en)

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CH112199 1999-06-16

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AR029165A1 true AR029165A1 (en) 2003-06-18

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WO2001017973A2 (en) * 1999-09-07 2001-03-15 Syngenta Participations Ag Novel herbicides
PT1481970E (en) 1999-09-07 2006-07-31 Syngenta Participations Ag NEW HERBICIDES
WO2001017351A1 (en) 1999-09-07 2001-03-15 Syngenta Participations Ag Herbicidal composition
TWI313676B (en) * 2002-12-05 2009-08-21 Syngenta Participations Ag Process for the preparation of phenylmalonic acid dinitriles
DE102004053191A1 (en) 2004-11-04 2006-05-11 Bayer Cropscience Ag 2,6-diethyl-4-methyl-phenyl substituted tetramic acid derivatives
TWI360533B (en) 2005-02-09 2012-03-21 Syngenta Participations Ag Process for the preparation of intermediates
JP5995445B2 (en) * 2009-03-12 2016-09-21 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ Method for preparing chloroaromatic compounds and bromoaromatic compounds
CN102964268A (en) * 2012-10-27 2013-03-13 安徽丰乐香料有限责任公司 Synthesis method of menthyl amide cooling agent
CN105061209B (en) * 2015-07-17 2017-03-22 河北诚信九天医药化工有限公司 Synthetic method of 2-diester methylmalonate compounds
CN109476588A (en) * 2016-07-22 2019-03-15 先正达参股股份有限公司 Method for preparing phenylmalonate dinitrile
PL3608324T3 (en) 2017-04-07 2022-03-14 Oriental (Luzhou) Agrochemicals. Co., Ltd. Method for preparing 2-arylmalonamide and applications of this method
WO2018210616A1 (en) 2017-05-15 2018-11-22 Bayer Cropscience Aktiengesellschaft Process for producing (4-halogeno-2,6-dialkylphenyl)malononitriles
EP3810585A1 (en) * 2018-06-22 2021-04-28 Bayer Aktiengesellschaft Process for preparing tricyclic compounds
CN109320435B (en) * 2018-11-30 2021-11-23 江苏富鼎化学有限公司 Synthesis method of 2- (2, 6-diethyl-4-methylbenzene) malononitrile
AU2019387370A1 (en) 2018-11-30 2021-06-10 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
CN109627184A (en) * 2019-01-04 2019-04-16 浙江中山化工集团股份有限公司 A kind of preparation method of 2,6- diethyl -4- aminomethyl phenyl malononitrile
ES3047864T3 (en) 2019-04-01 2025-12-05 Oriental Luzhou Agrochemicals Co Ltd Method for preparing 2-arylmalonic acid derivative, intermediate, and application thereof
CN110218153A (en) * 2019-07-10 2019-09-10 江苏丰山集团股份有限公司 A kind of preparation method of midbody compound 2,6- diethyl -4- methylbenzene malonate
CN110950778A (en) * 2019-12-24 2020-04-03 安徽省化工研究院 Process and catalyst system for preparing aromatic malononitrile

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MXPA01012485A (en) 2002-06-04
IL146337A0 (en) 2002-07-25
AU5682200A (en) 2001-01-09
ZA200109838B (en) 2002-09-25
EP1185506A1 (en) 2002-03-13
CN1355786A (en) 2002-06-26
KR20020012274A (en) 2002-02-15
BR0011700A (en) 2002-03-05
WO2000078712A1 (en) 2000-12-28
PL352102A1 (en) 2003-07-28
JP2003502403A (en) 2003-01-21
CA2368827A1 (en) 2000-12-28

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