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AR123502A1 - NEW PICOLINAMIDE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI - Google Patents

NEW PICOLINAMIDE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI

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AR123502A1
AR123502A1 ARP210102541A ARP210102541A AR123502A1 AR 123502 A1 AR123502 A1 AR 123502A1 AR P210102541 A ARP210102541 A AR P210102541A AR P210102541 A ARP210102541 A AR P210102541A AR 123502 A1 AR123502 A1 AR 123502A1
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Argentina
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alkyl
alkoxy
ring
group
cycloalkyl
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ARP210102541A
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Spanish (es)
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Sachin Baban Narute
Chandrashekhar Lilachand Patil
Rohit Saxena
Ramdas Balu Gadakh
Garg Ruchi
Santosh Shridhar Autkar
Alexander G M Klausener
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Pi Industries Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/82Biocides, 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
    • 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00Fungicides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04Ortho-condensed systems

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
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  • Mycology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicación 1: Un compuesto de fórmula (1) en donde, R¹ se selecciona entre el grupo que consiste en hidroxi, halógeno, alquilo C₁-C₆, haloalquilo C₁-C₆, cicloalquilo C₃-C₆, alcoxi C₁-C₆, cicloalquiloxi C₃-C₆, alquiltio C₁-C₆, cicloalquiltio C₁-C₆, -NHR⁹ y -N(R⁹)₂; R¹ᵃ se selecciona entre el grupo que consiste en hidroxi, halógeno, alquilo C₁-C₆, cicloalquilo C₃-C₆, haloalquilo C₁-C₆ y alcoxi C₁-C₆; R² se selecciona entre el grupo que consiste en hidrógeno, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, -SOₙ-alquilo C₁-C₆, -C(O)-R⁹, -C(O)-OR⁹, -(CH₂)ₘ-O-C(O)-R⁹, -C(O)-N(R⁹)₂, -(CH₂)ₘ-O-C(O)-N(R⁹)₂; R³ se selecciona entre el grupo que consiste en hidrógeno, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, cicloalquilo C₃-C₆, cicloalquil C₃-C₆-alquilo C₁-C₆, -(CH₂)ₘ-OR⁹, -(CH₂)ₘ-C(O)-R⁹, -(CH₂)ₘ-C(O)-OR⁹, -(CH₂)ₘ-C(O)-N(R⁹)₂, -(CH₂)ₘ-O-C(O)-OR⁹, -(CH₂)ₘ-O-C(O)-N(R⁹)₂ y -(CH₂)ₘ-C(O)-alcoxi C₁-C₆; o R² y R³ junto con los átomos a los que están unidos pueden formar un anillo heterocíclico de seis miembros; y uno o más átomos de C del anillo pueden reemplazarse opcionalmente por C(=O), C(=S), C=NR²ᵃ o CR²ᵃN(R²ᵃ)₂; en donde el anillo heterocíclico puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R²ᵃ; o R³ y R⁴ junto con los átomos a los que están unidos pueden formar un anillo heterocíclico no aromático de 5 a 6 miembros; en donde el heteroátomo adicional de dicho anillo se selecciona entre N, O ó S(=O)₀₋₂ y uno o más átomos de C del anillo pueden reemplazarse opcionalmente por C(=O), C(=S) o C(=NR⁹); el anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R³ᵃ; R²ᵃ se selecciona entre el grupo que consiste en halógeno, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, cicloalquilo C₃-C₈ y alcoxi C₁-C₄-alquilo C₁-C₄; R³ᵃ se selecciona entre el grupo que consiste en halógeno, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, cicloalquilo C₃-C₈ y alcoxi C₁-C₄-alquilo C₁-C₄; W representa O ó S; R⁴ y R⁵ se seleccionan independientemente entre el grupo que consiste en hidrógeno, halógeno, alquilo C₁-C₆, alquenilo C₂-C₆, alquinilo C₂-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, cicloalquilo C₃-C₆, cicloalquil C₃-C₆-alquilo C₁-C₆, arilo C₆-C₁₀, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; cada grupo de R⁴ y R⁵ puede estar opcionalmente sustituido con uno o más grupos seleccionados entre R⁴ᵃ; o R⁴ y R⁵ junto con los átomos a los que están unidos pueden formar un anillo carbocíclico no aromático o anillo heterocíclico no aromático de 3 a 6 miembros; en donde el heteroátomo de dicho anillo se selecciona entre N, O ó S(=O)₀₋₂ y uno o más átomos de C del anillo pueden reemplazarse opcionalmente por C(=O) o C(=S) o C(=NR⁹); el anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R⁴ᵃ; R⁴ᵃ se selecciona entre el grupo que consiste en halógeno, ciano, nitro, hidroxilo, tiol, amino, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, haloalcoxi C₁-C₆, alquiltio C₁-C₆, haloalquiltio C₁-C₆, cicloalquilo C₃-C₈ y alcoxi C₁-C₄-alquilo C₁-C₄; el anillo A representa un anillo heterocíclico de cinco o seis miembros; en donde el heteroátomo de dicho anillo se selecciona entre N, O, S(=O)₀₋₂, y uno o más átomos de C del anillo o el sistema de anillo pueden reemplazarse opcionalmente por C(=O), C(=S) o C(=NR⁹); dicho anillo A puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de RA; RA se selecciona entre el grupo que consiste en halógeno, hidroxi, alquilo C₁-C₆, alcoxi C₁-C₄, haloalquilo C₁-C₆, haloalcoxi C₁-C₄ y arilo C₆-C₁₀; R⁶ se selecciona entre el grupo que consiste en hidrógeno, halógeno, hidroxi, alquilo C₁-C₆, alcoxi C₁-C₄, haloalquilo C₁-C₆, haloalcoxi C₁-C₄ y arilo C₆-C₁₀; R⁷ y R⁸ se seleccionan independientemente entre el grupo que consiste en hidroxi, halógeno, alquilo C₁-C₆, alquenilo C₂-C₆, alquinilo C₂-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, cicloalquilo C₃-C₆, cicloalquil C₃-C₆-alquilo C₁-C₆, arilo C₆-C₁₀, aralquilo C₇-C₁₄, ariloxi C₆-C₁₀, ariltio C₆-C₁₀, aril C₆-C₁₀-alcoxi C₁-C₆, heterociclilo C₃-C₁₀ y heterocicliloxi C₃-C₁₀; cada grupo de R⁷ y R⁸ puede estar opcionalmente sustituido con uno o más grupos seleccionados entre R⁷ᵃ; o R⁷ᵃ se selecciona entre el grupo que consiste en ciano, halógeno, nitro, hidroxilo, tiol, amino, alquilo C₁-C₆, alquenilo C₂-C₆, alquinilo C₂-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, cicloalquilo C₃-C₆, cicloalquil C₃-C₆-alquilo C₁-C₆, fenilo, bencilo, feniltio, fenil-alcoxi C₁-C₆, heterociclilo C₃-C₁₀ y heterocicliloxi C₃-C₁₀; R⁷ y R⁸ junto con los átomos a los que están unidos pueden formar un anillo o sistema de anillo carbocíclico aromático o no aromático o anillo o sistema de anillo heterocíclico aromático o no aromático de 3 a 14 miembros; en donde el heteroátomo del anillo heterocíclico aromático se selecciona entre N, O y S; en donde el heteroátomo de dicho anillo o sistema de anillo se selecciona entre N, O ó S(=O)₀₋₂ y uno o más átomos de C del anillo o el sistema de anillo pueden reemplazarse opcionalmente por C(=O), C(=S) o C(=NR⁹); el anillo o sistema de anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R⁸ᵃ; con la condición de que cuando R⁷ y R⁸ forman un anillo aromático, entonces R⁶ está ausente; R⁸ᵃ se selecciona entre el grupo que consiste en halógeno, ciano, nitro, hidroxilo, tiol, amino, alquilo C₁-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₄-alquilo C₁-C₄, haloalcoxi C₁-C₆, alquiltio C₁-C₆, haloalquiltio C₁-C₆, cicloalquilo C₃-C₈, fenilo, bencilo, y heterociclilo C₃-C₁₀; R⁹ se selecciona entre el grupo que consiste en hidrógeno, formilo, alquilo C₁-C₄, alquenilo C₂-C₄, alquinilo C₂-C₄, haloalquilo C₁-C₄, cicloalquilo C₃-C₅, cicloalquil C₃-C₅-alquilo C₁-C₃, arilo C₆-C₁₀, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; cada grupo de R¹ a R⁹; R¹ᵃ, R²ᵃ, RA, R⁴ᵃ, R⁷ᵃ y R⁸ᵃ puede estar opcionalmente sustituido con uno o más grupos seleccionados entre el grupo que consiste en halógeno, ciano, nitro, R’, OR’, SR’, N(R’)₂, COR’ y CON(R’)₂; R’ se seleccionan independientemente entre el grupo que consiste en hidrógeno, alquilo C₁-C₄, alquenilo C₂-C₄, alquinilo C₂-C₄, haloalquilo C₁-C₄, haloalquenilo C₂-C₄, haloalquinilo C₂-C₄, alcoxi C₁-C₄, haloalcoxi C₁-C₄, cicloalquilo C₃-C₆, halocicloalquilo C₃-C₆, arilo C₆-C₁₀, aril C₆-C₁₀-alcoxi C₁-C₄, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; n es un número entero seleccionado de 0 a 2 y m es un número entero seleccionado de 0 a 3; y/o N-óxidos, complejos metálicos, isómeros, polimorfos y sales agrícolamente aceptables del mismo.Claim 1: A compound of formula (1) wherein R¹ is selected from the group consisting of hydroxy, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ cycloalkyloxy , C₁-C₆ alkylthio, C₁-C₆ cycloalkylthio, -NHR⁹ and -N(R⁹)₂; R¹ᵃ is selected from the group consisting of hydroxy, halogen, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, and C₁-C₆ alkoxy; R² is selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy-C₁-C₆ alkyl, -SOₙ-C₁-C₆ alkyl, -C(O)-R⁹, -C( O)-OR⁹, -(CH₂)ₘ-O-C(O)-R⁹, -C(O)-N(R⁹)₂, -(CH₂)ₘ-O-C(O)-N(R⁹)₂; R³ is selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy-C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl-C₁-C₆ alkyl , -(CH₂)ₘ-OR⁹, -(CH₂)ₘ-C(O)-R⁹, -(CH₂)ₘ-C(O)-OR⁹, -(CH₂)ₘ-C(O)-N(R⁹) ₂, -(CH₂)ₘ-O-C(O)-OR⁹, -(CH₂)ₘ-O-C(O)-N(R⁹)₂ and -(CH₂)ₘ-C(O)-C₁-C₆ alkoxy; or R² and R³ together with the atoms to which they are attached can form a six-membered heterocyclic ring; and one or more ring C atoms may be optionally replaced by C(=O), C(=S), C=NR²ᵃ or CR²ᵃN(R²ᵃ)₂; wherein the heterocyclic ring can be optionally substituted with one or more groups the same or different from R²ᵃ; or R³ and R⁴ together with the atoms to which they are attached can form a 5- to 6-membered non-aromatic heterocyclic ring; wherein the additional heteroatom on said ring is selected from N, O or S(=O)₀₋₂ and one or more C ring atoms may optionally be replaced by C(=O), C(=S) or C( =NR⁹); the ring can be optionally substituted with one or more groups the same or different from R³ᵃ; R²ᵃ is selected from the group consisting of halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₃-C₈ cycloalkyl, and C₁-C₄ alkoxy-C₁-C₄ alkyl; R³ᵃ is selected from the group consisting of halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₃-C₈ cycloalkyl, and C₁-C₄ alkoxy-C₁-C₄ alkyl; W represents O or S; R⁴ and R⁵ are independently selected from the group consisting of hydrogen, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy-C₁-C₆ alkyl , C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl-C₁-C₆ alkyl, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; each group of R⁴ and R⁵ may be optionally substituted with one or more groups selected from R⁴ᵃ; or R⁴ and R⁵ together with the atoms to which they are attached may form a 3- to 6-membered non-aromatic carbocyclic ring or non-aromatic heterocyclic ring; wherein said ring heteroatom is selected from N, O, or S(=O)₀₋₂ and one or more C ring atoms may optionally be replaced by C(=O) or C(=S) or C(= NR⁹); the ring may be optionally substituted with one or more groups the same or different from R⁴ᵃ; R⁴ᵃ is selected from the group consisting of halogen, cyano, nitro, hydroxy, thiol, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio , C₃-C₈ cycloalkyl and C₁-C₄ alkoxy-C₁-C₄ alkyl; ring A represents a five or six membered heterocyclic ring; wherein the heteroatom of said ring is selected from N, O, S(=O)₀₋₂, and one or more C atoms of the ring or ring system may optionally be replaced by C(=O), C(= S) or C(=NR⁹); said ring A may be optionally substituted with one or more groups the same or different from RA; RA is selected from the group consisting of halogen, hydroxy, C₁-C₆ alkyl, C₁-C₄ alkoxy, C₁-C₆ haloalkyl, C₁-C₄ haloalkoxy, and C₆-C₁₀ aryl; R⁶ is selected from the group consisting of hydrogen, halogen, hydroxy, C₁-C₆ alkyl, C₁-C₄ alkoxy, C₁-C₆ haloalkyl, C₁-C₄ haloalkoxy, and C₆-C₁₀ aryl; R⁷ and R⁸ are independently selected from the group consisting of hydroxy, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy-C₁-C₆ alkyl , C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl-C₁-C₆ alkyl, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl, C₆-C₁₀ aryloxy, C₆-C₁₀ arylthio, C₆-C₁₀ aryl-C₆C₁₂-heterocyclyl and C₃-C₁₀ heterocyclyloxy; each group of R⁷ and R⁸ may be optionally substituted with one or more groups selected from R⁷ᵃ; or R⁷ᵃ is selected from the group consisting of cyano, halogen, nitro, hydroxy, thiol, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-alkoxy C₆-C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl-C₁-C₆ alkyl, phenyl, benzyl, phenylthio, phenyl-C₁-C₆ alkoxy, C₃-C₁₀ heterocyclyl and C₃-C₁₀ heterocyclyloxy; R⁷ and R⁸ together with the atoms to which they are attached may form a 3- to 14-membered aromatic or non-aromatic carbocyclic ring or ring system or 3- to 14-membered aromatic or non-aromatic heterocyclic ring or ring system; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein the heteroatom of said ring or ring system is selected from N, O or S(=O)₀₋₂ and one or more C atoms of the ring or ring system may optionally be replaced by C(=O), C(=S) or C(=NR⁹); the ring or ring system may be optionally substituted with one or more groups the same or different from R⁸ᵃ; provided that when R⁷ and R⁸ form an aromatic ring, then R⁶ is absent; R⁸ᵃ is selected from the group consisting of halogen, cyano, nitro, hydroxy, thiol, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₄ alkoxy-C₁-C₄ alkyl, C₁-C₆ haloalkoxy , C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkyl, phenyl, benzyl, and C₃-C₁₀ heterocyclyl; R⁹ is selected from the group consisting of hydrogen, formyl, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₃-C₅ cycloalkyl, C₃-C₅ cycloalkyl-C₁-C₃ alkyl, C₆ aryl -C₁₀, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; each group from R¹ to R⁹; R¹ᵃ, R²ᵃ, RA, R⁴ᵃ, R⁷ᵃ and R⁸ᵃ may be optionally substituted with one or more groups selected from the group consisting of halogen, cyano, nitro, R, OR, SR, N(R)₂, COR and CON(R)₂; R are independently selected from the group consisting of hydrogen, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₁-C₄ alkoxy, C₁ haloalkoxy -C₄, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₆-C₁₀ aryl, C₆-C₁₀ aryl-C₁-C₄ alkoxy, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; n is an integer selected from 0 to 2 and m is an integer selected from 0 to 3; and/or N-oxides, metal complexes, isomers, polymorphs, and agriculturally acceptable salts thereof.

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