AR041181A1 - HERBICIDE TENYLALKINS AND PROCEDURE FOR PREPARING SUCH COMPOUNDS - Google Patents

HERBICIDE TENYLALKINS AND PROCEDURE FOR PREPARING SUCH COMPOUNDS

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AR041181A1
AR041181A1 ARP030102331A AR041181A1 AR 041181 A1 AR041181 A1 AR 041181A1 AR P030102331 A ARP030102331 A AR P030102331A AR 041181 A1 AR041181 A1 AR 041181A1
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Argentina
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alkyl
substituted
twice
phenyl
represents hydrogen
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Estos compuestos son adecuados para ser utilizados como herbicidas y se utilizan para combatir malas hierbas en los cultivos de plantas útiles. Reivindicación 1: Compuestos de la fórmula (1) en la cual n representa 0, 1, 2, 3, 4 ó 5; cada uno de los R1 independientemente de los demás, representa halógeno, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9, -C(R10)=NOR11, -COR12, -OR13, -SR14, -SOR15, -SO2R16, -OSO2R17, alquilo C1-8, alquenilo C2-8, alquinilo o cicloalquilo C3-6; o representa alquilo C1-8, alquenilo C2-8 o alquinilo C2-8 substituidos de una a cinco veces con halógeno o substituidos una, dos o tres veces con -CN, -NO2, -NR18R19, - CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(alquiltio)=NR28, -OR29, -SR30, -SOR31, -SO2R32 o con cicloalquilo C3-6; y/o cada uno de los R1 independientemente de los demás, representa cicloalquilo C3-6 substituido de una a cinco veces con halógeno y/o substituido una, dos o tres veces con -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(alquiltio)=NR28, -SR30, -SOR31, -SO2R32 o cicloalquilo; y/o cada uno de los R1 independientemente de los demás, representa fenilo, que por su parte puede estar substituido de una a cinco veces con halógeno y/o substituido una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; y/o dos R1 adyacentes juntos forman un puente C1-C7alquileno C1-7, que puede estar interrumpido por 1 o 2 átomos de oxígeno no adyacentes y que puede estar substituido con alquilo C1-6, siendo la cantidad total de átomos de anillo por lo menos de 5 y a lo sumo de 9; y/o dos R1 adyacentes juntos forman un puente alquenileno C2-7, que puede estar interrumpido por 1 o 2 átomos de oxígeno no adyacentes y que puede estar substituido con alquilo C1-6, siendo la cantidad total de átomos de anillo por lo menos de 5 y a lo sumo de 9; R3 y R4 independientemente entre sí, representan hidrógeno, halógeno, -CN, alquilo C1-4 o alcoxi C1-4; o R3 y R4 juntos forman alquileno C2-5; R5 representa hidrógeno o alquilo C1-8; R6 representa hidrógeno, alquilo C1-8,alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno, y/o substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o con alquilsulfonilo C1-4; o R5 y R6 conjuntamente son una cadena alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o de azufre; R7 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 substituidos de una a cinco veces con halógeno o substituidos una, dos o tres veces con alcoxi C1-4 o fenilo, pudiendo fenilo por su parte estar substituido de una a cinco veces con halógeno y/o substituido una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R8 representa hidrógeno o alquilo C1-8; R9 representa hidrógeno o alquilo C1-8, o alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN; o R9 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R8 y R9 representan conjuntamente alquileno C2-5; R10 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R11 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R12 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R13 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8; o R13 representa fenilo o fenil--alquilo C1-6, pudiendo por su parte los anillos fenilo estar substituidos de una a cinco veces con halógeno y/o substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2 o -S(O)2alquilo C1-8; o R13 representa alquilo C1-8 substituido de una a cinco veces con halógeno o substituidos una, dos o tres veces con -CN o alcoxi C1-4; R14 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno o substituidos una, dos o tres veces con -CN o alcoxi C1-4; R15, R16 y R17 independientemente entre sí, representan alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno o substituidos una, dos o tres veces con -CN o alcoxi C1-4; R18 representa hidrógeno o alquilo C1-8; R19 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o estar substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R18 y R19 representan conjuntamente una cadena alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno de azufre; R20 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno. o substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R21 representa hidrógeno o alquilo C1-8; R22 representa hidrógeno o alquilo C1-8, o alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN, o R22 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o con alquilsulfonilo C1-4; o R21 y R22 conjuntamente representan alquileno C2-5; R23 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R24 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R25 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R26 representa hidrógeno o alquilo C1-8; R27 representa hidrógeno o alquilo C1-8, o es alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN; o R27 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo a su vez estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R26 y R27 conjuntamente representan alquileno C2-5; R28 representa hidrógeno o alquilo C1-8; R29 y R30 independientemente entre sí, representan hidrógeno, alquilo C1-8, alquenilo C3-8 o -alquinilo C3-8, o son alquilo C1-8 substituido de una a cinco veces con halógeno o substituido una, dos o tres veces con -CN o alcoxi C1-4; R31 y R32 independientemente entre sí, representan alquilo C1-8,alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno o una, dos o tres veces con -CN o alcoxi C1-4; m vale 0, 1, 2 o 3; cada uno de los R2 independientemente entre sí, representa halógeno, -CN, -SCN, -SF5, -NO2, -NR36R37, -CO2R38, -CONR39R40, C(R41)=NOR42, -COR43, -OR44, -SR45, -SOR46, -SO2R47, -OSO2R48, -N([CO]pR49)COR50, -N(OR51)COR52, -N(R53)CO2R54 o -N-ftalimida; R36 representa hidrógeno o alquilo C1-6; y R37 representa hidrógeno, alquilo C1-8,alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo a su vez estar substituidos de una a cinco veces con halógeno o estar substituido una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, -alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R36 y R37 conjuntamente representan una cadena alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o por un átomo de azufre; R38 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 substituidos de una a cinco veces con halógeno o una, dos o tres veces con alcoxi C1-4 o fenilo, pudiendo fenilo por su parte estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R39 representa hidrógeno o alquilo C1-8; R40 representa hidrógeno o alquilo C1-8, o alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN; o R40 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo a su vez estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R39 y R40 juntos representan alquileno C3-5; R41 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R42 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R43 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R44 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8; o R44 representa fenilo o fenil-alquilo C1-6, pudiendo el anillo fenilo por su parte estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2 o -S(O)2alquilo C1-8, o R44 representa alquilo C1-8 substituido de una a cinco veces con halógeno o una, dos o tres veces con -CN o alcoxi C1-4; R45 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco These compounds are suitable for use as herbicides and are used to combat weeds in useful plant crops. Claim 1: Compounds of the formula (1) in which n represents 0, 1, 2, 3, 4 or 5; each of the R1 independently of the others, represents halogen, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9, -C (R10) = NOR11, -COR12, -OR13, -SR14 , -SOR15, -SO2R16, -OSO2R17, C1-8 alkyl, C2-8 alkenyl, C3-6 alkynyl or cycloalkyl; or represents C1-8 alkyl, C2-8 alkenyl or C2-8 alkynyl substituted one to five times with halogen or substituted once, twice or three times with -CN, -NO2, -NR18R19, - CO2R20, -CONR21R22, -COR23 , -C (R24) = NOR25, -C (S) NR26R27, -C (alkylthio) = NR28, -OR29, -SR30, -SOR31, -SO2R32 or with C3-6 cycloalkyl; and / or each of the R1 independently of the others, represents C3-6 cycloalkyl substituted one to five times with halogen and / or substituted once, twice or three times with -CN, -NO2, -NR18R19, -CO2R20, - CONR21R22, -COR23, -C (R24) = NOR25, -C (S) NR26R27, -C (alkylthio) = NR28, -SR30, -SOR31, -SO2R32 or cycloalkyl; and / or each of the R1 independently of the others, represents phenyl, which in turn can be substituted one to five times with halogen and / or substituted once, twice or three times with C1-4 alkyl, C1-4 haloalkyl , C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; and / or two adjacent R1 together form a C1-C7 C1-7 alkylene bridge, which may be interrupted by 1 or 2 non-adjacent oxygen atoms and which may be substituted with C1-6 alkyl, the total amount of ring atoms being at least 5 and at most 9; and / or two adjacent R1 together form a C2-7 alkenylene bridge, which may be interrupted by 1 or 2 non-adjacent oxygen atoms and which may be substituted with C1-6 alkyl, the total amount of ring atoms being at least of 5 and at most 9; R3 and R4 independently of each other, represent hydrogen, halogen, -CN, C1-4 alkyl or C1-4 alkoxy; or R3 and R4 together form C2-5 alkylene; R5 represents hydrogen or C1-8 alkyl; R 6 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, phenyl or benzyl, whereby phenyl and benzyl can be substituted one to five times with halogen, and / or substituted once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or with C1-4 alkylsulfonyl; or R5 and R6 together are a C2-5 alkylene chain, which may be interrupted by an oxygen or sulfur atom; R7 represents hydrogen, C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, or C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl substituted one to five times with halogen or substituted once, twice or three times with C1-4 alkoxy or phenyl, with phenyl being able to be substituted one to five times with halogen and / or substituted once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN , -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; R8 represents hydrogen or C1-8 alkyl; R9 represents hydrogen or C1-8 alkyl, or C1-8 alkyl substituted once, twice or three times with -COOH, C1-8 alkoxycarbonyl or -CN; or R9 represents C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, with phenyl and benzyl being able to be substituted one to five times with halogen and / or substituted once, twice or three times with C1-4 alkyl, haloalkyl C1-4, C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; or R8 and R9 together represent C2-5 alkylene; R 10 represents hydrogen, C 1-4 alkyl, C 1-4 haloalkyl or C 3-6 cycloalkyl; R 11 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, C 1-4 haloalkyl or C 3-6 haloalkenyl; R12 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl or C3-6 cycloalkyl; R13 represents hydrogen, C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl; or R13 represents phenyl or phenyl-C1-6 alkyl, and the phenyl rings may be substituted one to five times with halogen and / or substituted once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN, -NO2 or -S (O) 2 C1-8 alkyl; or R13 represents C1-8 alkyl substituted one to five times with halogen or substituted once, twice or three times with -CN or C1-4 alkoxy; R14 represents hydrogen, C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, or C1-8 alkyl substituted one to five times with halogen or substituted once, twice or three times with -CN or C1-4 alkoxy; R15, R16 and R17 independently of each other, represent C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, or C1-8 alkyl substituted one to five times with halogen or substituted once, twice or three times with -CN or C1-4 alkoxy; R18 represents hydrogen or C1-8 alkyl; R19 represents hydrogen, C1-8 alkyl, C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, whereby phenyl and benzyl can be substituted one to five times with halogen and / or substituted once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; or R18 and R19 together represent a C2-5 alkylene chain, which may be interrupted by a sulfur oxygen atom; R 20 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, phenyl or benzyl, whereby phenyl and benzyl can be substituted one to five times with halogen. or substituted once, twice or three times with C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, -CN, -NO 2, C 1-4 alkylthio, C 1-4 alkylsulfinyl or C 1-4 alkylsulfonyl; R21 represents hydrogen or C1-8 alkyl; R22 represents hydrogen or C1-8 alkyl, or C1-8 alkyl substituted once, twice or three times with -COOH, C1-8 alkoxycarbonyl or -CN, or R22 represents C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, Phenyl and benzyl may be substituted once or five times with halogen and / or once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN, -NO2, C1-alkylthio 4, C 1-4 alkylsulfinyl or with C 1-4 alkylsulfonyl; or R21 and R22 together represent C2-5 alkylene; R23 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl or C3-6 cycloalkyl; R24 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl or C3-6 cycloalkyl; R25 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, C 1-4 haloalkyl or C 3-6 haloalkenyl; R26 represents hydrogen or C1-8 alkyl; R27 represents hydrogen or C1-8 alkyl, or is C1-8 alkyl substituted once, twice or three times with -COOH, C1-8 alkoxycarbonyl or -CN; or R27 represents C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, and phenyl and benzyl may be substituted once to five times with halogen and / or once, twice or three times with C1-4 alkyl, C1 haloalkyl -4, C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; or R26 and R27 together represent C2-5 alkylene; R28 represents hydrogen or C1-8 alkyl; R29 and R30 independently of each other, represent hydrogen, C1-8 alkyl, C3-8 alkenyl or -C3-8 alkynyl, or are C1-8 alkyl substituted one to five times with halogen or substituted once, twice or three times with - CN or C1-4 alkoxy; R31 and R32 independently of each other, represent C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, or C1-8 alkyl substituted one to five times with halogen or once, twice or three times with -CN or C1- alkoxy 4; m is worth 0, 1, 2 or 3; each of the R2 independently of each other, represents halogen, -CN, -SCN, -SF5, -NO2, -NR36R37, -CO2R38, -CONR39R40, C (R41) = NOR42, -COR43, -OR44, -SR45, - SOR46, -SO2R47, -OSO2R48, -N ([CO] pR49) COR50, -N (OR51) COR52, -N (R53) CO2R54 or -N-phthalimide; R36 represents hydrogen or C1-6 alkyl; and R37 represents hydrogen, C1-8 alkyl, C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, and phenyl and benzyl may in turn be substituted one to five times with halogen or substituted once, twice or three times with C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, -CN, -NO 2, C 1-4 alkylthio, C 1-4 alkylsulfinyl or C 1-4 alkylsulfonyl; or R36 and R37 together represent a C2-5 alkylene chain, which may be interrupted by an oxygen atom or a sulfur atom; R38 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl or C 3-8 alkynyl, or C 1-8 alkyl, C 3-8 alkenyl or C 3-8 alkynyl substituted one to five times with halogen or once, twice or three times with C1-4 alkoxy or phenyl, with phenyl being able to be substituted one to five times with halogen and / or once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, -CN, - NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; R39 represents hydrogen or C1-8 alkyl; R40 represents hydrogen or C1-8 alkyl, or C1-8 alkyl substituted once, twice or three times with -COOH, C1-8 alkoxycarbonyl or -CN; or R40 represents C3-8 alkenyl, C3-8 alkynyl, phenyl or benzyl, and phenyl and benzyl may in turn be substituted one to five times with halogen and / or once, twice or three times with C1-4 alkyl, C1 haloalkyl -4, C1-4 alkoxy, -CN, -NO2, C1-4 alkylthio, C1-4 alkylsulfinyl or C1-4 alkylsulfonyl; or R39 and R40 together represent C3-5 alkylene; R41 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl or C3-6 cycloalkyl; R42 represents hydrogen, C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, C 1-4 haloalkyl or C 3-6 haloalkenyl; R43 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl or C3-6 cycloalkyl; R44 represents hydrogen, C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl; or R44 represents phenyl or phenyl-C 1-6 alkyl, the phenyl ring being able to be substituted one to five times with halogen and / or once, twice or three times with C1-4 alkyl, C1-4 haloalkyl, C1 alkoxy -4, -CN, -NO2 or -S (O) 2 C1-8alkyl, or R44 represents C1-8 alkyl substituted one to five times with halogen or once, twice or three times with -CN or C1-4 alkoxy; R45 represents hydrogen, C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, or C1-8 alkyl substituted from one to five

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