AR123501A1 - NEW PICOLINAMIDE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI - Google Patents

NEW PICOLINAMIDE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI

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AR123501A1
AR123501A1 ARP210102540A ARP210102540A AR123501A1 AR 123501 A1 AR123501 A1 AR 123501A1 AR P210102540 A ARP210102540 A AR P210102540A AR P210102540 A ARP210102540 A AR P210102540A AR 123501 A1 AR123501 A1 AR 123501A1
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alkyl
alkoxy
cycloalkyl
group
ring
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Sachin Baban Narute
Rahul Deshmukh
Vinoth Perumal
Rohit Saxena
Vishal A Mahajan
Ruchi Garg
Santosh Shridhar Autkar
Alexander G M Klausener
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Pi Industries Ltd
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    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/90—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic 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
    • C07D498/04—Ortho-condensed systems

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic 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, -NHR¹³ y -N(R¹³)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)-R¹³, -C(O)-OR¹³, -(CH₂)ₘ-O-C(O)-R¹³, -C(O)-N(R¹³)₂ y -(CH₂)ₘ-O-C(O)-N(R¹³)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-OR¹³, -(CH₂)ₘ-C(O)-R¹³, -(CH₂)ₘ-C(O)-OR¹³, -(CH₂)ₘ-C(O)-N(R¹³)₂, -(CH₂)ₘ-O-C(O)-OR₁₃, -(CH₂)ₘ-O-C(O)-N(R¹³)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) o C(=S); 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 uno o más heteroátomos de dicho anillo se seleccionan 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(=NR¹³); 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; Z se selecciona entre Z¹ a Z⁴, del grupo de fórmulas (2); * representa un punto de unión; R⁶ y R⁶ᵃ se seleccionan independientemente 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, -C(O)-R¹³, -(CH₂)ₘC(O)-R¹³ y -(CH₂)ₘ-C(O)-alcoxi C₁-C₆; R⁷ se selecciona entre el grupo que consiste en hidrógeno, 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, alcoxicarbonilo C₁-C₆, alquilsulfinilo C₁-C₆, alquilsulfonilo C₁-C₆, arilo C₆-C₁₀, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; cada grupo de R⁷ puede estar opcionalmente sustituido con uno o más grupos seleccionados entre 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; R⁷ᵃ se selecciona entre el grupo que consiste en hidrógeno, alquilo C₁-C₆, alquenilo C₂-C₆, alquinilo C₂-C₆, haloalquilo C₁-C₆, alcoxi C₁-C₆, alcoxi C₁-C₆-alquilo C₁-C₆, cicloalquilo C₃-C₆ y cicloalquil C₃-C₆-alquilo C₁-C₆; o R⁷ y R⁷ᵃ 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), C(=S) o C(=NR¹³); el anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R⁷ᵇ; R⁷ᵇ 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, arilo C₆-C₁₀, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; R⁸, R⁸ᵃ, R⁹ y R⁹ᵃ se seleccionan independientemente entre el grupo que consiste en hidrógeno, 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 R⁸, R⁸ᵃ, R⁹ y R⁹ᵃ puede estar opcionalmente sustituido con uno o más grupos seleccionados entre R¹⁰; o R⁸ y R⁹ junto con los átomos a los que están unidos pueden formar un anillo carbocíclico aromático o no aromático o anillo heterocíclico aromático o no aromático de 3 a 10 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), C(=S) o C(=NR¹³); el anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R¹¹; con la condición de que cuando R⁸ y R⁹ forman un anillo aromático, entonces R¹² está ausente; o R⁷ y R⁹ junto con los átomos a los que están unidos pueden formar un anillo carbocíclico aromático o no aromático o anillo heterocíclico aromático o no aromático de 3 a 10 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), C(=S) o C(=NR¹³); el anillo puede estar opcionalmente sustituido con uno o más grupos iguales o diferentes de R¹¹; R¹⁰ 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; R¹¹ 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, arilo C₆-C₁₀, aralquil C₇-C₁₄ y heterociclilo C₃-C₁₀; R¹² se selecciona entre el grupo de hidrógeno, halógeno, hidroxi, alquilo C₁-C₆, alcoxi C₁-C₄, haloalquilo C₁-C₆ y haloalcoxi C₁-C₄; R¹³ 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 R¹³ y R¹ᵃ, R²ᵃ, R³ᵃ, R⁴ᵃ, R⁵ᵃ, R⁶ᵃ, R⁷ᵃ, R⁷ᵇ, R⁸ᵃ, R⁹ᵃ 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, halógeno, ciano, 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, aril C₆-C₁₀-alcoxi C₁-C₄, arilo C₆-C₁₀, 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 o sales agrícolamente aceptables del mismo; con la condición de que los siguientes compuestos se excluyan de la definición de fórmula (1), acetato de 2-(((2S)-1-((1-(4-ciclohexilfenil)etil)(metil)amino)-1-oxopropan-2-il)carbamoil)-4-metoxipiridin-3-ilo; N-((2S)-1-((1-(4-ciclohexilfenil)etil)(metil)amino)-1-oxopropan-2-il)-3-hidroxi-4-metoxipicolinamida; (S)-N-(1-(bencilamino)-1-oxo-3-fenilpropan-2-il)-3,4-dihidroxipicolinamida; (S)-3,4-dihidroxi-N-(1-(isobutilamino)-1-oxo-3-fenilpropan-2-il)picolinamida; (S)-N-(1-(bencilamino)-1-oxopropan-2-il)-3,4-dihidroxipicolinamida; N-(2-(bencilamino)-2-oxoetil)-3,4-dihidroxipicolinamida; (S)-3,4-dihidroxi-N-(1-(isobutilamino)-1-oxopropan-2-il)picolinamida; 3,4-dihidroxi-N-(2-(isobutilamino)-2-oxoetil)picolinamida; clorhidrato de (S)-N-(1-(bencilamino)-1-oxo-3-fenilpropan-2-il)-3,4-dihidroxipicolinamida; clorhidrato de (S)-3,4-dihidroxi-N-(1-(isobutilamino)-1-oxo-3-fenilpropan-2-il)picolinamida; clorhidrato de (S)-N-(1-(bencilamino)-1-oxopropan-2-il)-3,4-dihidroxipicolinamida; clorhidrato de N-(2-(bencilamino)-2-oxoetil)-3,4-dihidroxipicolinamida; clorhidrato de (S)-3,4-dihidroxi-N-(1-(isobutilamino)-1-oxopropan-2-il)picolinamida y clorhidrato de 3,4-dihidroxi-N-(2-(isobutilamino)-2-oxoetil)picolinamida.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, -NHR¹³ and -N(R¹³)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)-R¹³, -C( O)-OR¹³, -(CH₂)ₘ-O-C(O)-R¹³, -C(O)-N(R¹³)₂ and -(CH₂)ₘ-O-C(O)-N(R¹³)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-OR¹³, -(CH₂)ₘ-C(O)-R¹³, -(CH₂)ₘ-C(O)-OR¹³, -(CH₂)ₘ-C(O)-N(R¹³) ₂, -(CH₂)ₘ-O-C(O)-OR₁₃, -(CH₂)ₘ-O-C(O)-N(R¹³)₂ and -(CH₂)ₘ-C(O)-C₁-C₆alkoxy; 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) or C(=S); 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 one or more heteroatoms on said ring are 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 (=NR¹³); 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; Z is selected from Z¹ to Z⁴, from the group of formulas (2); * represents a junction point; R⁶ and R⁶ᵃ are independently 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-alkyl C₁-C₆, -C(O)-R¹³, -(CH₂)ₘC(O)-R¹³ and -(CH₂)ₘ-C(O)-C₁-C₆alkoxy; R⁷ is selected from the group consisting of hydrogen, 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, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; each group of R⁷ may be optionally substituted with one or more groups selected from halogen, cyano, nitro, hydroxy, thiol, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-alkylthio C₆, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkyl and C₁-C₄ alkoxy-C₁-C₄ alkyl; R⁷ᵃ is selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy-C₁-C₆ alkyl, C₃-C₆ cycloalkyl and C₃-C₆ cycloalkyl-C₁-C₆ alkyl; or R⁷ and R⁷ᵃ 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 the heteroatom of 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(= NR¹³); the ring may be optionally substituted with one or more groups the same or different from R⁷ᵇ; R⁷ᵇ 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, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; R⁸, R⁸ᵃ, R⁹ and R⁹ᵃ are independently selected from the group consisting of hydrogen, hydroxy, halogen, 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, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl, C₆-C₁₀ aryloxy, C₆-C₁₀ arylthio, C₆-C₁₁alkyl aryl C₆, C₃-C₁₀ heterocyclyl and C₃-C₁₀ heterocyclyloxy; each group of R⁸, R⁸ᵃ, R⁹ and R⁹ᵃ may be optionally substituted with one or more groups selected from R¹⁰; or R⁸ and R⁹ together with the atoms to which they are attached can form a 3 to 10 membered aromatic or non-aromatic carbocyclic ring or aromatic or non-aromatic heterocyclic ring; wherein the heteroatom of 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(= NR¹³); the ring can be optionally substituted with one or more groups the same or different from R¹¹; provided that when R⁸ and R⁹ form an aromatic ring, then R¹² is absent; or R⁷ and R⁹ together with the atoms to which they are attached can form a 3 to 10 membered aromatic or non-aromatic carbocyclic ring or aromatic or non-aromatic heterocyclic ring; wherein the heteroatom of 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(= NR¹³); the ring can be optionally substituted with one or more groups the same or different from R¹¹; R¹⁰ 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-C₆ alkoxy -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; R¹¹ 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, C₆-C₁₀ aryl, C₇-C₁₄ aralkyl and C₃-C₁₀ heterocyclyl; R¹² is selected from the group of hydrogen, halogen, hydroxy, C₁-C₆ alkyl, C₁-C₄ alkoxy, C₁-C₆ haloalkyl, and C₁-C₄ haloalkoxy; R¹³ 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 R¹³ and R¹ᵃ, R²ᵃ, R³ᵃ, R⁴ᵃ, R⁵ᵃ, R⁶ᵃ, R⁷ᵃ, R⁷ᵇ, R⁸ᵃ, R⁹ᵃ 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, halogen, cyano, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₁-alkoxy C₄, C₁-C₄ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₆-C₁₀ aryl-C₁-C₄ alkoxy, C₆-C₁₀ aryl, 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, or agriculturally acceptable salts thereof; provided that the following compounds are excluded from the definition of formula (1), 2-(((2S)-1-((1-(4-cyclohexylphenyl)ethyl)(methyl)amino)-1- oxopropan-2-yl)carbamoyl)-4-methoxypyridin-3-yl; N-((2S)-1-((1-(4-cyclohexylphenyl)ethyl)(methyl)amino)-1-oxopropan-2-yl)-3-hydroxy-4-methoxypicolinamide; (S)-N-(1-(benzylamino)-1-oxo-3-phenylpropan-2-yl)-3,4-dihydroxypicolinamide; (S)-3,4-dihydroxy-N-(1-(isobutylamino)-1-oxo-3-phenylpropan-2-yl)picolinamide; (S)-N-(1-(benzylamino)-1-oxopropan-2-yl)-3,4-dihydroxypicolinamide; N-(2-(benzylamino)-2-oxoethyl)-3,4-dihydroxypicolinamide; (S)-3,4-dihydroxy-N-(1-(isobutylamino)-1-oxopropan-2-yl)picolinamide; 3,4-dihydroxy-N-(2-(isobutylamino)-2-oxoethyl)picolinamide; (S)-N-(1-(benzylamino)-1-oxo-3-phenylpropan-2-yl)-3,4-dihydroxypicolinamide hydrochloride; (S)-3,4-dihydroxy-N-(1-(isobutylamino)-1-oxo-3-phenylpropan-2-yl)picolinamide hydrochloride; (S)-N-(1-(benzylamino)-1-oxopropan-2-yl)-3,4-dihydroxypicolinamide hydrochloride; N-(2-(benzylamino)-2-oxoethyl)-3,4-dihydroxypicolinamide hydrochloride; (S)-3,4-dihydroxy-N-(1-(isobutylamino)-1-oxopropan-2-yl)picolinamide hydrochloride and 3,4-dihydroxy-N-(2-(isobutylamino)-2- oxoethyl)picolinamide.

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