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AR107738A1 - ACID AMIDES N- (5-HALOGEN-1,3,4-OXADIAZOL-2-IL) ARYLBARBOXYL AND ITS USE AS HERBICIDES - Google Patents

ACID AMIDES N- (5-HALOGEN-1,3,4-OXADIAZOL-2-IL) ARYLBARBOXYL AND ITS USE AS HERBICIDES

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AR107738A1
AR107738A1 ARP170100474A ARP170100474A AR107738A1 AR 107738 A1 AR107738 A1 AR 107738A1 AR P170100474 A ARP170100474 A AR P170100474A AR P170100474 A ARP170100474 A AR P170100474A AR 107738 A1 AR107738 A1 AR 107738A1
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Argentina
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alkyl
halogen
cycloalkyl
heterocyclyl
alkynyl
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ARP170100474A
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Spanish (es)
Inventor
Armin Sausen
Tiebes Jrg Dr
Rosinger Christopher Dr
Gatzweiler Elmar Dr
Dietrich Hansjrg Dr
Ahrens Hartmut Dr
Waldraff Christian Dr
Khn Arnim Dr
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Bayer Cropscience Ag
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Publication of AR107738A1 publication Critical patent/AR107738A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Se describen amidas de ácido N-(5-halógen-1,3,4-oxadiazol-2-il)arilcarboxílico útiles como herbicidas. Reivindicación 1: Amidas del ácido N-(5-halógen-1,3,4-oxadiazol-2-il)arilcarboxílico de la fórmula (1), y sus sales, en donde los sustituyentes tienen los siguientes significados: A es N o CY; Hal es halógeno; X es nitro, halógeno, ciano, formilo, rodano, alquilo C₁₋₆, halógeno-alquilo C₁₋₆, alquenilo C₂₋₆, halógeno-alquenilo C₂₋₆, alquinilo C₂₋₆, halógen-alquinilo C₃₋₆, cicloalquil C₃₋₆, halógen-cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, halógen-cicloalquil C₃₋₆-alquilo C₁₋₆, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R², S(O)ₙR², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-CO₂R¹, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, alquil C₁₋₆-heteroarilo, alquil C₁₋₆-heterociclilo, en donde los dos últimos radicales mencionados están sustituidos por s radicales del grupo compuesto por halógeno, alquilo C₁₋₆, halógenalquilo C₁₋₆, S(O)ₙ-alquilo C₁₋₆, alcoxi C₁₋₆ y halógenalcoxi C₁₋₆, y en donde heterociclilo lleva n grupos oxo; Y es hidrógeno, nitro, halógeno, ciano, rodano, alquilo C₁₋₆, halógen-alquilo C₁₋₆, alquenilo C₂₋₆, halógen-alquenilo C₂₋₆, alquinilo C₂₋₆, halógen-alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógen-cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, halógen-cicloalquil C₃₋₆-alquilo C₁₋₆, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)ₙR², SO₂OR¹, SO₂N(R¹)₂, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-CO₂R¹, alquil C₁₋₆-CN, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, alquil C₁₋₆-fenilo, alquil C₁₋₆-heteroarilo, alquil C₁₋₆-heterociclilo, fenilo, heteroarilo o heterociclilo, en donde los últimos seis radicales mencionados están sustituidos por s radicales del grupo compuesto por halógeno, nitro, ciano, alquilo C₁₋₆, halógen-alquilo C₁₋₆, cicloalquilo C₃₋₆, S(O)ₙ-alquilo C₁₋₆, alcoxi C₁₋₆, halógen-alcoxi C₁₋₆, alcoxi C₁₋₆-alquilo C₁₋₄ y cianometilo, y en donde heterociclilo lleva n grupos oxo; Z es hidrógeno, halógeno, ciano, rodano, alquilo C₁₋₆, alcoxi C₁₋₆, halógen-alquilo C₁₋₆, alquenilo C₂₋₆, halógeno-alquenilo C₂₋₆, alquinilo C₂₋₆, halógen-alquinilo C₂₋₆, cicloalquilo C₃₋₆, halógen-cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, halógen-cicloalquil C₃₋₆-alquilo C₁₋₆, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)ₙR², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-CO₂R¹, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, heteroarilo, heterociclilo o fenilo, en donde los últimos tres radicales mencionados están sustituidos por s radicales del grupo compuesto por halógeno, nitro, ciano, alquilo C₁₋₆, halógen-alquilo C₁₋₆, cicloalquilo C₃₋₆, S(O)ₙ-alquilo C₁₋₆, alcoxi C₁₋₆ y halógen-alcoxi C₁₋₆, y en donde heterociclilo lleva n grupos oxo; o V es hidrógeno, nitro, halógeno, ciano, alquilo C₁₋₄, halógen-alquilo C₁₋₄, OR¹, S(O)ₙR²; W es hidrógeno, halógeno, alquilo C₁₋₄, halógen-alquilo C₁₋₄, OR¹, S(O)ₙR²; R¹ es hidrógeno, alquilo C₁₋₆, halógen-alquilo C₁₋₆, alquenilo C₂₋₆, halógen-alquenilo C₂₋₆, alquinilo C₂₋₆, halógen-alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógen-cicloalquilo C₃₋₆, alquil C₁₋₆-O-alquilo C₁₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, fenilo, fenil-alquilo C₁₋₆, heteroarilo, alquil C₁₋₆-heteroarilo, heterociclilo, alquil C₁₋₆-heterociclilo, alquil C₁₋₆-O-heteroarilo, alquil C₁₋₆-O-heterociclilo, alquil C₁₋₆-NR³-heteroarilo, alquil C₁₋₆-NR³-heterociclilo, en donde los últimos 21 radicales mencionados están sustituidos por s radicales del grupo compuesto por ciano, halógeno, nitro, rodano, OR³, S(O)ₙR⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ y alcoxi C₁₋₄-alcoxi C₂₋₆-carbonilo, y en donde heterociclilo lleva n grupos oxo; R² es alquilo C₁₋₆, halógen-alquilo C₁₋₆, alquenilo C₂₋₆, halógen-alquenilo C₂₋₆, alquinilo C₂₋₆, halógen-alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógen-cicloalquilo C₃₋₆, alquil C₁₋₆-O-alquilo C₁₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, fenilo, fenil-alquilo C₁₋₆, heteroarilo, alquil C₁₋₆-heteroarilo, heterociclilo, alquil C₁₋₆-heterociclilo, alquil C₁₋₆-O-heteroarilo, alquil C₁₋₆-O-heterociclilo, alquil C₁₋₆-NR³-heteroarilo, alquil C₁₋₆-NR³-heterociclilo, en donde los últimos 21 radicales mencionados están sustituidos por s radicales del grupo compuesto por ciano, halógeno, nitro, rodano, OR³, S(O)ₙR⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂ R⁴, CO₂R³, COSR⁴, CON(R³)₂ y alcoxi C₁₋₄-alcoxi C₂₋₆-carbonilo, y en donde heterociclilo lleva n grupos oxo; R³ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆ o cicloalquil C₃₋₆-alquilo C₁₋₆; R⁴ es alquilo C₁₋₆, alquenilo C₂₋₆ o alquinilo C₂₋₆; R⁵ es metilo o etilo; n es 0, 1 ó 2; s es 0, 1, 2 ó 3; con la condición de que se excluya el compuesto N¹-(5-cloro-1,3,4-oxadiazol-2-il)-N²,N²-dietil-3-yodoftalamida.N- (5-Halogen-1,3,4-oxadiazol-2-yl) arylcarboxylic acid amides useful as herbicides are described. Claim 1: N- (5-halogen-1,3,4-oxadiazol-2-yl) arylcarboxylic acid amides of the formula (1), and salts thereof, wherein the substituents have the following meanings: A is N or CY; Hal is halogen; X is nitro, halogen, cyano, formyl, rhodan, C₁₋₆ alkyl, halogen C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ halogen-alkenyl, C₂₋₆ alkynyl, C₃₋₆ halogen-alkynyl, C₃ cycloalkyl ₋₆, halogen-C₃₋₆-cycloalkyl, C₃₋₆-cycloalkyl-C alquilo-alkyl, halogen-C₃₋₆ -cycloalkyl-C₁₋₆-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C (O) N (R¹) ₂, NR¹C (O) N (R¹) ₂, OC (O) N (R¹) ₂, C (O) NR¹OR¹, OR¹, OCOR¹, OSO₂R², S (O) ₙR², SO₂OR¹, SO₂N (R¹) ₂, NR¹SO₂R², NR¹COR¹, C₁₋₆-S (O) ₙR² alkyl, C₁₋₆-OR¹ alkyl, C₁₋₆-OCOR¹ alkyl, C₁₋₆-OSO₂R² alkyl, C₁₋₆-CO₂R¹ alkyl, C₁₋₆-SO₂OR¹ alkyl, C₁₋₆ alkyl -CON (R¹) ₂, C₁₋₆-SO₂N (R¹) ₂ alkyl, C₁₋₆-NR¹COR¹ alkyl, C₁₋₆-NR¹SO₂R² alkyl, NR¹R², P (O) (OR⁵) ₂, CH₂P (O) (OR⁵) ₂, C₁₋₆-heteroaryl alkyl, C₁₋₆-heterocyclyl alkyl, wherein the last two radicals mentioned are n substituted by s radicals of the group consisting of halogen, C₁₋₆ alkyl, Có halogenalkyl, S (O) alquiloC alquilo alkyl, C₁₋₆ alkoxy and C₁₋₆ halogenalkoxy, and where heterocyclyl carries n oxo groups ; Y is hydrogen, nitro, halogen, cyano, rhodan, C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ halogen-alkenyl, C₂₋₆ alkynyl, C₂₋₆ halogen-alkynyl, C₃ cycloalkyl ₋₆, C₃₋₆ cycloalkenyl, C₃₋₆ halogen-cycloalkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl, halogen-C₃₋₆ cycloalkyl-C alquilo alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C (O) N (R¹) ₂, NR¹C (O) N (R¹) ₂, OC (O) N (R¹) ₂, CO (NOR¹) R¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S (O) ₙR², SO₂OR¹, SO₂N (R¹ ) ₂, C₁₋₆-S (O) alkyl ₙR², C₁₋₆-OR¹ alkyl, C₁₋₆-OCOR¹ alkyl, C₁₋₆-OSO₂R² alkyl, C₁₋₆-CO₂R¹ alkyl, C₁₋₆-CN alkyl, alkyl C₁₋₆-SO₂OR¹, C₁₋₆-CON (R¹) ₂ alkyl, C₁₋₆-SO₂N (R¹) ₂ alkyl, C₁₋₆-NR¹COR¹ alkyl, C₁₋₆-NR¹SO₂R² alkyl, N (R¹) ₂, P ( O) (OR⁵) ₂, CH₂P (O) (OR⁵) ₂, C₁₋₆-phenyl alkyl, C₁₋₆-heteroaryl alkyl, C₁₋ alkyl Hetero-heterocyclyl, phenyl, heteroaryl or heterocyclyl, wherein the last six radicals mentioned are substituted by s radicals of the group consisting of halogen, nitro, cyano, C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₃₋₆ cycloalkyl (O) ₙ-C₁₋₆ alkyl, C₁₋₆ alkoxy, halogen-C₁₋₆ alkoxy, C₁₋₆ alkoxy-C₁₋₄ alkyl and cyanomethyl, and wherein heterocyclyl carries n oxo groups; Z is hydrogen, halogen, cyano, rhodan, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ halogen-alkyl, C₂₋₆ alkenyl, C₂₋₆ halogen-alkenyl, C₂₋₆ alkynyl, C₂₋₆ halogen-alkynyl , C₃₋₆ cycloalkyl, C₃₋₆ halogen-cycloalkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl, halogen-C₃₋₆ -cycloalkyl-C alquilo alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C (O) N (R¹ ) ₂, NR¹C (O) N (R¹) ₂, OC (O) N (R¹) ₂, C (O) NR¹OR¹, OSO₂R², S (O) ₙR², SO₂OR¹, SO₂N (R¹) ₂, NR¹SO₂R², NR¹COR¹, alkyl C₁₋₆-S (O) ₙR², C₁₋₆-OR¹ alkyl, C₁₋₆-OCOR¹ alkyl, C₁₋₆-OSO₂R² alkyl, C₁₋₆-CO₂R¹ alkyl, C₁₋₆-SO₂OR¹ alkyl, C₁₋₆- alkyl CON (R¹) ₂, C₁₋₆-SO₂N (R¹) ₂ alkyl, C₁₋₆-NR¹COR¹ alkyl, C₁₋₆-NR¹SO₂R² alkyl, N (R¹) ₂, P (O) (OR⁵) ₂, heteroaryl, heterocyclyl or phenyl, wherein the last three radicals mentioned are substituted by radicals of the group com placed by halogen, nitro, cyano, C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₃₋₆ cycloalkyl, S (O) ₙ -C alquilo alkyl, C₁₋₆ alkoxy and C₁₋₆ halogen-alkoxy, and in where heterocyclyl carries n oxo groups; or V is hydrogen, nitro, halogen, cyano, C₁₋₄ alkyl, halogen-C₁₋₄ alkyl, OR¹, S (O) ₙR²; W is hydrogen, halogen, C₁₋₄ alkyl, halogen-C₁₋₄ alkyl, OR¹, S (O) ₙR²; R¹ is hydrogen, C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ halogen-alkenyl, C₂₋₆ alkynyl, C₂₋₆ halogen-alkynyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkenyl, halogen-C₃₋₆-cycloalkyl, C₁₋₆-O-alkyl-C₁₋₆, cycloalkyl-C₁₋₆-alkyl, phenyl, phenyl-C alquilo-alkyl, heteroaryl, C₁₋₆-heteroaryl, heterocyclyl, alkyl C₁₋₆-heterocyclyl, C₁₋₆-O-heteroaryl alkyl, C₁₋₆-O-heterocyclyl alkyl, C₁₋₆-NR³-heteroaryl alkyl, C₁₋₆-NR³-heterocyclyl alkyl, wherein the last 21 radicals mentioned are substituted by radical s of the group consisting of cyano, halogen, nitro, rhodan, OR³, S (O) ₙR⁴, N (R³) ₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON (R³) ₂ and C₁₋₄-C₂₋₆-carbonyl alkoxy, and wherein heterocyclyl carries n oxo groups; R² is C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ halogen-alkenyl, C₂₋₆ alkynyl, C₂₋₆ halogen-alkynyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkenyl, halogen C₃₋₆ cycloalkyl, C₁₋₆-O-C₁₋₆ alkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl, phenyl, phenyl-C₁₋₆ alkyl, heteroaryl, C₁₋₆-heteroaryl alkyl, heterocyclyl, C₁₋ alkyl ₆-heterocyclyl, C₁₋₆-O-heteroaryl alkyl, C₁₋₆-O-heterocyclyl alkyl, C₁₋₆-NR³-heteroaryl alkyl, C₁₋₆-NR³-heterocyclyl alkyl, wherein the last 21 radicals mentioned are substituted by s radicals of the group consisting of cyano, halogen, nitro, rhodan, OR³, S (O) ₙR⁴, N (R³) ₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂ R⁴, CO₂R³, COSR⁴, CON (R³) ₂ and C₁₋₄-C₂₋₆-carbonyl alkoxy, and wherein heterocyclyl carries n oxo groups; R³ is hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl or C₃₋₆ cycloalkyl-C alquilo alkyl; R⁴ is C₁₋₆ alkyl, C₂₋₆ alkenyl or C₂₋₆ alkynyl; R⁵ is methyl or ethyl; n is 0, 1 or 2; s is 0, 1, 2 or 3; with the proviso that the compound N¹- (5-chloro-1,3,4-oxadiazol-2-yl) -N², N²-diethyl-3-iodophthalamide is excluded.

ARP170100474A 2016-02-24 2017-02-24 ACID AMIDES N- (5-HALOGEN-1,3,4-OXADIAZOL-2-IL) ARYLBARBOXYL AND ITS USE AS HERBICIDES AR107738A1 (en)

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WO2020108518A1 (en) * 2018-11-30 2020-06-04 青岛清原化合物有限公司 N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or salt thereof, preparation method therefor, herbicidal composition and use thereof
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