AR064851A1 - SERINAMIDS SUBTITUTED BY BENZOIL - Google Patents

SERINAMIDS SUBTITUTED BY BENZOIL

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Publication number
AR064851A1
AR064851A1 ARP080100114A ARP080100114A AR064851A1 AR 064851 A1 AR064851 A1 AR 064851A1 AR P080100114 A ARP080100114 A AR P080100114A AR P080100114 A ARP080100114 A AR P080100114A AR 064851 A1 AR064851 A1 AR 064851A1
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Argentina
Prior art keywords
alkyl
alkoxy
aminocarbonyl
atom
alkylcarbonyl
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ARP080100114A
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Spanish (es)
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Basf Ag
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Publication of AR064851A1 publication Critical patent/AR064851A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18Carbamic 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/44Biocides, 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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46N-acyl derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/64Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/84Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D321/00Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/12Eight-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/04Systems containing only non-condensed rings with a four-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La presente se refiere a serinamidas substituidas por benzoílo y a sus sales utiles en la agricultura. Procesos y compuestos intermedios para su preparacion, y uso de estos compuestos, o de composiciones que comprenden estos compuestos, para controlar las plantas no deseadas. Reivindicacion 1: Una serinamida sustituida por benzoilo, de la formula (1), caracterizada porque las variables son como se define en lo que sigue: R1 es halogeno, ciano, alquilo C1-6, haloalquilo C1-6 o haloalcoxi C1-6; R2, R3, R4, R5 son hidrogeno, halogeno, ciano, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6 o haloalcoxi C1-6; R6, R7 son hidrogeno, hidroxilo o alcoxi C1-6; R8 es alquilo C1-6, cianoalquilo C1-4 o haloalquilo C1-6; R9 es hidrogeno, alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, alquinilo C3-6, haloalquenilo C3-6, haloalquinilo C3-6, formilo, alquilcarbonilo C1-6, cicloalquilcarbonilo C1-6, alquenilcarbonilo C2-6, alquinilcarbonilo C1-6, alcoxicarbonilo C1-6, alqueniloxicarbonilo C3-6, alquiniloxicarbonilo C3-6, aminocarbonilo, alquilaminocarbonilo C1-6, alquenilaminocarbonilo C3-6, alquinilaminocarbonilo C3-6, alquilsulfonilaminocarbonilo C1-6, di-alquilo C1-6-aminocarbonilo, N-alquenil C1-6-N-alquilo C1-6-aminocarbonilo, N-alquinil C3-6-N-alquilo C1-6-aminocarbonilo, N-alcoxi C1-6-N-alquilo C1-6-aminocarbonilo, N-alquenilo C3-6-N-alcoxi C1-6-aminocarbonilo, N-alquinilo C1-6-N-alcoxi C1-6-aminocarbonilo, alquilaminotiocarbonilo C1-6, di-alquilo C1-6-aminotiocarbonilo, alquilo C1-6-cianoimino, amino-cianoimino, [alquilo C1-6-amino-cianoimino, [di-alquilo C1-6-amino]cianoimino, alquilcarbonil C1-6-alquilo C1-6, alcoxiimino C1-6-alquilo C1-6, N-alquilamino C1-6-imino-alquilo-C1-6, N-di- alquilamino C1-6-imino-alquilo C1-6 o tri-alquil sililo C1-4, en donde los radicales alquilo, cicloalquilo y alcoxi mencionados pueden estar parcialmente o completamente halogenados y/o pueden llevar de uno a tres de los grupos siguientes: ciano, hidroxilo, cicloalquilo C3-6, alcoxi C1-6-alquilo C1-4, alcoxi C1-4-alcoxi C1-4-alquilo C1-4, alcoxi C1-4, alquiltio C1-4, di-alquilo C1-4-amino, alquilo C1-4-alcoxicarbonilamino C1-4, alquilcarbonilo C1-4, hidroxi carbonilo, alcoxicarbonilo C1-4, aminocarbonilo, alquilaminocarbonilo C1-4, di-alquilo C1-4-aminocarbonil o alquilcarboniloxi C1-4; fenilo, fenil-alquilo C1-6, fenilcarbonilo, fenilcarbonilo-alquilo C1-6, fenoxicarbonilo, fenilaminocarbonilo, fenilsulfonilaminocarbonilo, N-alquilo C1-6-N-fenil-aminocarbonilo, alquilcarbonilo C1-6-alquilo C1-6, en donde el radical fenilo puede estar parcial o totalmente halogenado y/o puede llevar de uno a tres de los grupos siguientes: ciano, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4; o SO2R12; R10 y R11 en conjunto con el átomo de carbono al cual están fijados, son un anillo de 3 a 12 miembros saturado o parcialmente insaturado que es carbocíclico o que contiene de 1 a 3 átomos de nitrogeno, de 0 a 3 átomos de nitrogeno y 1 átomo de oxígeno o átomo de azufre, de 0 a 2 átomos de nitrogeno y 2 átomos de oxígeno o de azufre, 0 o 1 átomo de nitrogeno y 1 átomo de oxígeno y 1 átomo de azufre, 3 átomos de oxígeno o de azufre, 2 átomos de oxígeno y 1 átomo de azufre, o 1 átomo de oxígeno y 2 átomos de azufre, en donde el anillo está sin sustituir o está substituido por 1 a 3, en el caso del halogeno hasta la máxima cantidad posible, substituyentes seleccionados del grupo consistente en halogeno, ciano, nitro, alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, alquinilo C3-6, haloalquenilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, alqueniloxi C3-6, alquiniloxi C3-6, trialquilsililoxi, formilo, alquilo C1-6-carbonilo, cicloalquilcarbonilo C3- 6, alquenilcarbonilo C2-6, alquinilcarbonilo C2-6, alcoxicarbonilo C1-6, alqueniloxicarbonilo C3-6, alquiniloxicarbonilo C3-6, aminocarbonilo, alquilaminocarbonilo C1-6, alquenilaminocarbonilo C3-6, alquinilaminocarbonilo C3-6, di-alquilo C1-6- aminocarbonilo, N-alquenilo C3-6-N-alquilo C1-6-aminocarbonilo, N-alquinilo C3-6-N-alquilo C1-6-aminocarbonilo, N-alcoxi C1-6-N-alquilo C1-6-amino-carbonilo, N-alquenilo C3-6-N-alcoxi C1-6-aminocarbonilo, N-alquiniIo C3-6-N-alcoxi C1-6- aminocarbonilo, di-alquilo C1-6-aminotiocarbonilo, alcoximino C1-6-alquilo C1-6, N-alquilamino C1-6-imino-alquilo C1-6 o N-dialquilamino C1-6-imino-alquilo C1-6, amino, formilamino, alquilcarbonilamino C1-6, alcoxi C1-6-carbonilamino, alquilamino C1- 6, formilalquil amino C1-6, alquilcarbonilo C1-6-alquilamino C1-6, alcoxicarbonilo C1-6, alquilamino C1-6, di-alquilo C1-6-amino, aminocarbonilamino, alquilaminocarbonilamino C1-6, di-C1-6alquilaminocarbonilamino, alquiltio C1-6, alquilsulfonilo C1- 6, alquilsulfoniloxi, alquilsulfonilamino, alquilsulfinilo C1-6, alquilsulfimino C1-6, alquil C1-6-alquilsulfimino C1-6, carbonilo, tiocarbonilo, imino, alquilimino, hidroxiimino, alcoxiimino, aminoimino, alquilaminoimino, di-alquilaminoimino, alquilcarbonilaminoimino, alquilsulfonilaminoimino, vinilideno C1-6, alcoxivinilideno C1-6, di-alquilC1-6-aminovinilideno, en donde los radicales alquilo, cicloalquilo y alcoxi mencionados pueden estar halogenados de manera parcial o total y/o pueden llevar de uno a tres de los grupos siguientes: ciano, hidroxilo, cicloalquilo C3-6, alcoxi C1-4, alquiltio C1-4, di-alquilo C1-4- amino, alquilcarbonilo C1-4, hidroxicarbonilo, alcoxicarbonilo C1-4, amino carbonilo, alquilaminocarbonilo C1-4, di-alquilo C1-4-aminocarbonilo o alquilcarboniloxi C1-4, fenilo, fenil-alquilo C1-4, fenilcarbonilo, fenilcarbonil-alquilo C1-6, fenoxi carbonilo, fenilaminocarbonilo, fenilsulfonilaminocarbonilo, N-alquilo C1-6-N-fenil-aminocarbonilo, fenil- alquilcarbonilo C1-6, heterociclilo, heterociclil-alquilo C1-6, heterociclilcarbonilo, heterociclilsulfonilaminocarbonilo; heterociclilcarbonil-alquilo C1-6, heterocicliloxicarbonilo, heterociclilaminocarbonilo, N-alquilo C1-6-N-heterociclil- aminocarbonilo, o heterociclil-alquilcarbonilo C1-6, en donde el radical fenilo y heterociclilo de los 17 substituyentes mencionados en ultimo término pueden estar halogenados de manera parcial o total y/o pueden llevar de uno a tres de los grupos siguientes: nitro, ciano, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4 y en donde el anillo es monociclico o está fusionado con otro anillo de 3 a 7 miembros, saturado, parcialmente insaturado o totalmente insaturado, que es carbocíclico o que contiene de 1 a 3 átomos de nitrogeno, de 0 a 2 átomos de nitrogeno y 1 átomo de oxígeno o átomo de azufre, de 1 a 1 átomo de nitrogeno y 2 átomos de oxígeno o de azufre, de 0 a 1 átomos de nitrogeno y 1 átomo de oxigeno y 1 átomo de azufre, 2 átomos de oxígeno y 1 átomo de azufre, o 1 átomo de oxígeno y 2 átomos de azufre, en donde el anillo fusionado está sin sustituir o está substituido por de 1 a 3, en el caso de halogeno también hasta la máxima cantidad posible, de substituyentes seleccionados del grupo consistente en halogeno, ciano, nitro, alquilo C1-6, alquenilo C1-6, haloalquilo C1-6, haloalquenilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, haloalcoxi C1-6 y alquilsulfonilo C1-6, y en donde el anillo no está conectado en puente, o está conectado en puente por medio de una cadena de 1 a 4 miembros saturada o insaturada, que no contiene heteroátomos o que contiene de 1 a 2 átomos de nitrogeno, 0 o 1 átomo de nitrogeno y 1 átomo de oxigeno o 1 átomo de azufre, de 0 a 1 átomo de nitrogeno y 2 átomos de oxígeno o 2 átomos de azufre, o de 0 a 1 átomo de nitrogeno y 1 átomo de oxígeno y 1 átomo de azufre, estando el puente sin sustituir o está substituido por de 1 a 3, en el caso de halogeno también hasta la contenedor máxima posible, de substituyentes seleccionados del grupo consistente en halogeno, ciano, nitro, alquilo C1-6, alquenilo C1-6, haloalquilo C1-6, haloalquenilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, haloalcoxi C1-6 y alquilsulfonilo C1-6; R12 es alquilo C1-6, haloalquilo C1-6 o fenilo, en donde el radical fenilo puede estar parcial o totalmente halogenado y/o puede llevar de uno a tres de los grupos siguientes: alquilo C1-6, haloalquilo C1-6 o alcoxi C1-6. o una sal de la misma, util desde el punto de vista de la agricultura. Reivindicacion 5: Un proceso para preparar serinamidas sustituidas por benzoilo de la formula (1) de acuerdo con una cualquiera de las reivindicaciones 1 a 4, caracterizado porque se hacen reaccionar derivados de serina de la formula (5), en donde R6, R9, R10 y R11 son como se define en la reivindicacion 1 y L1 es un grupo saliente desplazable desde el punto de vista nucleofilo se hacen reaccionar con ácidos benzoicos/ derivados de ácidos benzoicos de la formula (4) en donde R1 a R5 son como se define en la reivindicacion 1, y L2 es un grupo saliente desplazable desde el punto de vista nucleofilo de manera de obtener los correspondientes derivados de benzoilo de la formula (3) en donde R1 a R6 y R9 a R11 son como se definio en la reivindicacion 1 y L1 es un grupo saliente desplazable desde el punto de vista nucleofilo, y a continuacion se hacen reaccionar los derivados de benzoilo correspondientes (3) con una amina de la formula (2) HNR7R8 en donde R7 y R8 son como se definen en la reivindicacion 1.This refers to benzoyl substituted serinamides and their useful salts in agriculture. Processes and intermediate compounds for their preparation, and use of these compounds, or compositions comprising these compounds, to control unwanted plants. Claim 1: A benzoyl substituted serinamide of the formula (1), characterized in that the variables are as defined in the following: R 1 is halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl or C 1-6 haloalkoxy; R2, R3, R4, R5 are hydrogen, halogen, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy; R6, R7 are hydrogen, hydroxyl or C1-6 alkoxy; R8 is C1-6 alkyl, C1-4 cyanoalkyl or C1-6 haloalkyl; R 9 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-6 haloalkenyl, C 3-6 haloalkynyl, formyl, C 1-6 alkylcarbonyl, C 1-6 cycloalkylcarbonyl, C 2-6 alkenylcarbonyl , C 1-6 alkynylcarbonyl, C 1-6 alkoxycarbonyl, C 3-6 alkenyloxycarbonyl, C 3-6 alkyloxycarbonyl, aminocarbonyl, C 1-6 alkylaminocarbonyl, C 3-6 alkenylaminocarbonyl, C 1-6 alkylaminocarbonyl, C 1-6 alkylsulfonylaminocarbonyl aminocarbonyl, N-C 1-6 alkenyl-C 1-6 alkyl-aminocarbonyl, N-C 3-6 alkynyl-C 1-6 alkylcarbonyl, N-C 1-6 alkoxy-C 1-6 alkyl-aminocarbonyl, N-C3-6-N-C 1-6 alkoxy-aminocarbonyl, N-C 1-6 alkynyl-C 1-6 alkoxycarbonyl, C 1-6 alkylamino thiocarbonyl, C 1-6 alkyl-aminothiocarbonyl, C 1-6 alkyl -cyanoimino, amino-cyanoimino, [C1-6-amino-cyanoimino alkyl, [di-C1-6-amino] cyanoimino, C1-6 alkylcarbonyl-C1-6 alkyl, C1-6 alkoxyimino-C1-6 alkyl, N -C 1-6 alkylamino-imino-C 1-6 alkyl, N-di-alkylamin or C1-6-imino-C1-6 alkyl or tri-alkyl C1-4 alkyl, wherein the aforementioned alkyl, cycloalkyl and alkoxy radicals may be partially or completely halogenated and / or can lead from one to three of the following groups: cyano, hydroxy, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkoxy-C 1-4 alkoxy, C 1-4 alkoxy, C 1-4 alkylthio, C 1-4 alkyl -amino, C1-4 alkyl-C1-4 alkoxycarbonylamino, C1-4 alkylcarbonyl, hydroxycarbonyl, C1-4 alkoxycarbonyl, aminocarbonyl, C1-4 alkylaminocarbonyl, di-C1-4 alkyl-aminocarbonyl or C1-4 alkylcarbonyloxy; phenyl, phenyl-C 1-6 alkyl, phenylcarbonyl, phenylcarbonyl-C 1-6 alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N-C 1-6 alkyl-N-phenyl aminocarbonyl, C 1-6 alkylcarbonyl-C 1-6 alkyl, wherein the Phenyl radical may be partially or totally halogenated and / or may have one to three of the following groups: cyano, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy; or SO2R12; R10 and R11 together with the carbon atom to which they are attached, are a saturated or partially unsaturated 3 to 12-membered ring that is carbocyclic or that contains 1 to 3 nitrogen atoms, 0 to 3 nitrogen atoms and 1 oxygen atom or sulfur atom, 0 to 2 nitrogen atoms and 2 oxygen or sulfur atoms, 0 or 1 nitrogen atom and 1 oxygen atom and 1 sulfur atom, 3 oxygen or sulfur atoms, 2 oxygen atoms and 1 sulfur atom, or 1 oxygen atom and 2 sulfur atoms, where the ring is unsubstituted or substituted by 1 to 3, in the case of halogen up to the maximum possible amount, substituents selected from the group consisting of halogen, cyano, nitro, C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-6 haloalkenyl, C 3-6 haloalkynyl, hydroxy, C 1-6 alkoxy, C 3-6 alkenyloxy, C3-6 alkynyloxy, trialkylsilyloxy, formyl, C1-6 alkylcarbonyl, C3-6 cycloalkylcarbonyl, alken C2-6 ylcarbonyl, C2-6 alkynylcarbonyl, C1-6 alkoxycarbonyl, C3-6 alkenyloxycarbonyl, C3-6 alkynyloxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, C3-6 alkylaminocarbonyl, di- C 1-6 alkylcarbonyl , N-C3-6-N-C1-6-aminocarbonyl alkyl, N-C3-6-N-C1-6-aminocarbonyl alkyl, N- C1-6-N-C1-6-amino-carbonyl alkyl , C3-6-N-C 1-6 alkoxy-aminocarbonyl, C3-6-N-C 1-6 alkyloxycarbonyl, C 1-6 alkyl-aminothiocarbonyl, C 1-6 alkoxy-C 1-6 alkyl 6, N-C 1-6 alkylamino-imino-C 1-6 alkyl or N-dialkylamino C 1-6-imino-C 1-6 alkyl, amino, formylamino, C 1-6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, C 1-6 alkylamino , formylalkyl-C 1-6 alkyl, C 1-6 alkylcarbonyl-C 1-6 alkylamino, C 1-6 alkoxycarbonyl, C 1-6 alkylamino, C 1-6 -alkylamino, aminocarbonylamino, C 1-6 alkylaminocarbonylamino, di-C 1-6 alkylaminocarbonylamino, alkylthio C1-6, C1-6 alkylsulfonyl, alkylsulfonyloxy, alkyls ilsulfonylamino, C1-6 alkylsulfinyl, C1-6 alkylsulfimino, C1-6 alkyl C1-6 alkylsulfimino, carbonyl, thiocarbonyl, imino, alkylaminoimino, hydroxyimino, alkoxyimino, aminoimino, alkylaminoimino, di-alkylaminoimino, alkylaminoiminoimino-alkylaminoimino, alkylamino-vinylimino , C1-6 alkoxyvinylidene, di-C1-6-aminovinylidene alkyl, wherein the aforementioned alkyl, cycloalkyl and alkoxy radicals can be partially or totally halogenated and / or can carry from one to three of the following groups: cyano, hydroxyl, C 3-6 cycloalkyl, C 1-4 alkoxy, C 1-4 alkylthio, C 1-4 alkyl-amino, C 1-4 alkylcarbonyl, hydroxycarbonyl, C 1-4 alkoxycarbonyl, amino carbonyl, C 1-4 alkylaminocarbonyl, C 1-4 alkyl -aminocarbonyl or C 1-4 alkylcarbonyloxy, phenyl, phenylC 1-4 alkyl, phenylcarbonyl, phenylcarbonylC 1-6 alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N-C 1-6 alkyl-N-phenyl-aminocarbonyl, phenyl-C 1 alkylcarbonyl -6, heterocyclyl, heteroci C 1-6 alkyl-alkyl, heterocyclylcarbonyl, heterocyclylsulfonylaminocarbonyl; heterocyclylcarbonyl-C1-6 alkyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl, N-C1-6-N-heterocyclyl-aminocarbonyl, or heterocyclyl-alkylcarbonyl C1-6, wherein the phenyl and heterocyclyl radical of the last 17 substituents may be halogenated partially or totally and / or they can carry from one to three of the following groups: nitro, cyano, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy and wherein the ring is monocyclic or it is fused with another ring of 3 to 7 members, saturated, partially unsaturated or totally unsaturated, which is carbocyclic or containing 1 to 3 nitrogen atoms, 0 to 2 nitrogen atoms and 1 oxygen atom or sulfur atom, 1 to 1 nitrogen atom and 2 oxygen or sulfur atoms, 0 to 1 nitrogen atoms and 1 oxygen atom and 1 sulfur atom, 2 oxygen atoms and 1 sulfur atom, or 1 oxygen atom and 2 sulfur atoms, where the fusion ring ado is unsubstituted or substituted by 1 to 3, in the case of halogen also up to the maximum possible amount, of substituents selected from the group consisting of halogen, cyano, nitro, C1-6 alkyl, C1-6 alkenyl, C1 haloalkyl -6, C3-6 haloalkenyl, C3-6 haloalkynyl, hydroxy, C1-6 alkoxy, C1-6 haloalkoxy and C1-6 alkylsulfonyl, and wherein the ring is not bridged, or is bridged by means of a 1 to 4-member chain saturated or unsaturated, containing no heteroatoms or containing 1 to 2 nitrogen atoms, 0 or 1 nitrogen atom and 1 oxygen atom or 1 sulfur atom, 0 to 1 nitrogen atom and 2 oxygen atoms or 2 sulfur atoms, or 0 to 1 nitrogen atom and 1 oxygen atom and 1 sulfur atom, the bridge being unsubstituted or substituted by 1 to 3, in the case of halogen also up to the maximum possible container of substituents selected from the group consisting of halogen , cyano, nitro, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 haloalkyl, C 3-6 haloalkenyl, C 3-6 haloalkynyl, hydroxy, C 1-6 alkoxy, C 1-6 haloalkoxy and C 1-6 alkylsulfonyl; R12 is C1-6 alkyl, C1-6 haloalkyl or phenyl, wherein the phenyl radical may be partially or totally halogenated and / or may have one to three of the following groups: C1-6 alkyl, C1-6 haloalkyl or alkoxy C1-6. or a salt thereof, useful from the point of view of agriculture. Claim 5: A process for preparing benzoyl substituted serinamides of the formula (1) according to any one of claims 1 to 4, characterized in that serine derivatives of the formula (5) are reacted, wherein R6, R9, R10 and R11 are as defined in claim 1 and L1 is a nucleophilically movable leaving group reacted with benzoic acids / benzoic acid derivatives of the formula (4) wherein R1 to R5 are as defined in claim 1, and L2 is a nucleophilically movable leaving group so as to obtain the corresponding benzoyl derivatives of the formula (3) wherein R1 to R6 and R9 to R11 are as defined in claim 1 and L1 is a nucleophilically movable leaving group, and then the corresponding benzoyl derivatives (3) are reacted with an amine of the formula (2) HNR7R8 wherein R7 and R8 are as defined in r claim 1.

ARP080100114A 2007-01-11 2008-01-10 SERINAMIDS SUBTITUTED BY BENZOIL AR064851A1 (en)

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UY28683A1 (en) * 2003-12-19 2005-08-31 Basf Ag PHENYLALANINE- AMIDAS REPLACED BY BENZILO-
DE502005005420D1 (en) * 2004-09-16 2008-10-30 Basf Se BENZOYL SUBSTITUTED SERIN AMIDE
US7786046B2 (en) * 2005-05-25 2010-08-31 Basf Aktiengesellschaft Benzoyl-substituted serineamides
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