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AR120183A1 - HETEROARYL-PYRAZINE COMPOUNDS AS PESTICIDES - Google Patents

HETEROARYL-PYRAZINE COMPOUNDS AS PESTICIDES

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Publication number
AR120183A1
AR120183A1 ARP200102794A ARP200102794A AR120183A1 AR 120183 A1 AR120183 A1 AR 120183A1 AR P200102794 A ARP200102794 A AR P200102794A AR P200102794 A ARP200102794 A AR P200102794A AR 120183 A1 AR120183 A1 AR 120183A1
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Argentina
Prior art keywords
6alkyl
heterocyclyl
4alkyl
optionally
heteroaryl
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ARP200102794A
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Spanish (es)
Inventor
Turberg Andreas Dr
Heisler Iring Dr
Telser Joachim Dr
Arlt Alexander Dr
Dr Jeschke Peter Prof
Schwarz Hans Dr
- Dr Fsslein Martin Georg
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Bayer Animal Health Gmbh
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Publication of AR120183A1 publication Critical patent/AR120183A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • 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
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/16—Halogen atoms; Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/02—Heterocyclic 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
    • C07D417/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/14—Heterocyclic 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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Insects & Arthropods (AREA)
  • Veterinary Medicine (AREA)
  • Agronomy & Crop Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Compuestos derivados de heteroaril-pirazina, intermediarios para su preparación y su uso para el control de plagas de invertebrados, en particular, de insectos, arácnidos y nematodos como así también en el ámbito de la salud animal, es decir, en la medicina veterinaria contra endoparásitos y ectoparásitos. Reivindicación 1: Compuestos de la fórmula general (1), donde R¹ es hidrógeno; C₁₋₆alquilo, C₃₋₆cicloalquilo, C₃₋₆cicloalquilC₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆haloalquenilo, C₂₋₆alquinilo, C₂₋₆haloalquinilo, cada uno de los cuales opcionalmente puede estar sustituido; o fenil-C₁₋₆alquilo, en el cual fenilo opcionalmente está sustituido con 1 a 5 sustituyentes, cada uno de los cuales, considerado en forma independiente, se selecciona a partir del conjunto que consiste en halógeno, hidroxi, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, -SF₅, -NH₂, C₁₋₆alquilo, C₃₋₆cicloalquilo, C₃₋₆cianocicloalquilo, C₃₋₆halocicloalquilo, C₃₋₆cicloalquil-C₁₋₆alquilo, C₁₋₃haloalquilo, C₁₋₃cianoalquilo, C₁₋₄alcoxi, C₁₋₃haloalcoxi, C₁₋₃cianoalcoxi, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₁₋₃haloalquiltio, C₁₋₃haloalquilsulfinilo, C₁₋₃haloalquilsulfonilo, C₁₋₃cianoalquiltio, C₁₋₃cianoalquilsulfinilo, C₁₋₃cianoalquilsulfonilo; o heterociclil-C₁₋₆alquilo, siendo que el heterociclilo se selecciona a partir del conjunto que consiste en heterociclilo de 3 a 10 miembros saturado o parcialmente insaturado, heteroarilo de 5 miembros, heteroarilo de 6 miembros, heteroarilo de 9 miembros y heteroarilo de 10 miembros y el heterociclilo opcionalmente está sustituido con 1 a 5 sustituyentes, cada uno de los cuales, considerado en forma independiente, se selecciona a partir del conjunto que consiste en halógeno, hidroxi, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, -SF₅, -NH₂, C₁₋₆alquilo, C₃₋₆cicloalquilo, C₃₋₆cianocicloalquilo, C₃₋₆halocicloalquilo, C₃₋₆cicloalquil-C₁₋₆alquilo, C₁₋₃haloalquilo, C₁₋₃cianoalquilo, C₁₋₄alcoxi, C₁₋₃haloalcoxi, C₁₋₃cianoalcoxi, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₁₋₃haloalquiltio, C₁₋₃haloalquilsulfinilo, C₁₋₃haloalquilsulfonilo, C₁₋₃cianoalquiltio, C₁₋₃cianoalquilsulfinilo, C₁₋₃cianoalquilsulfonilo; R² es fenilo o un heteroarilo de 5 ó 6 miembros, cada uno de los cuales opcionalmente está sustituido con 1, 2 ó 3 sustituyentes a seleccionar, considerando cada uno en forma independiente, a partir del conjunto que consiste en halógeno, hidroxi, -CN, -COOH, -NO₂, -NH₂, -SF₅; y C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, C₃₋₆cicloalquilo, C₁₋₆haloalquilo, C₁₋₆alcoxi, C₃₋₆cicloalcoxi, C₁₋₆haloalcoxi, hidroxi-C₁₋₆alquilo, -CO₂C₁₋₆alquilo, -NH(C₁₋₆alquil), -N(C₁₋₆alquil)₂, S-C₁₋₆alquilsulfinimidoilo, S-C₃₋₆cicloalquilsulfinimidoilo, S-C₂₋₆alquenilsulfinimidoilo, S-C₂₋₆alquinil-sulfinimidoilo, S-fenil-sulfinimidoilo, S-heterociclil-sulfinimidoilo, S-heteroaril-sulfinimidoilo, S-C₁₋₆alquil-sulfonimidoilo, S-C₃₋₆cicloalquil-sulfonimidoilo, S-C₂₋₆alquenil-sulfonimidoilo, S-C₂₋₆alquinil-sulfonimidoilo, S-fenil-sulfonimidoilo, S-heterociclil-sulfonimidoilo, S-heteroaril-sulfonimidoilo, -C(=NOC₁₋₆alquil)H, -C(=NOC₁₋₆alquil)-C₁₋₆alquilo, (C₁₋₆alquil)₃-sililo, cada uno de los cuales opcionalmente puede estar sustituido; y las subestructuras S1 - S9, del grupo de fórmulas (2), en las cuales el enlace al fenilo o heteroarilo de 5 ó 6 miembros está marcado con un # y Z es CO o CS y Y considerado en forma independiente se selecciona a partir de CO o SO₂; R²¹ es hidrógeno o C₁₋₆alquilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo, -C₁₋₆alquil-C₃₋₆cicloalquilo, fenilo, heteroarilo y heterociclilo, cada uno de los cuales opcionalmente puede estar sustituido; R²² es hidrógeno o C₁₋₆alquilo, C₁₋₆haloalquilo, -C₁₋₆alquil-C₃₋₆cicloalquilo y C₃₋₆cicloalquilo, cada uno de los cuales opcionalmente puede estar sustituido; R²³ considerado en forma independiente se selecciona a partir de C₁₋₆alquilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo y fenilo, cada uno de los cuales opcionalmente puede estar sustituido; R²⁴ en cada caso opcionalmente está sustituido con C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo, fenilo, heteroarilo y heterociclilo; o R¹ y R²² conjuntamente con el átomo de nitrógeno al que están unidos, representan un heterociclilo monocíclico o policíclico de 3 a 12 miembros saturado o insaturado que puede contener otros heteroátomos; y heterociclilo de 3 a 6 miembros o un heteroarilo de 5 a 6 miembros cada uno de los cuales contiene 1 ó 2 heteroátomos a seleccionar a partir del conjunto que consiste en N, O, y S, siendo que el heterociclilo de 3 a 6 miembros o el heteroarilo de 5 a 6 miembros sustituyente opcionalmente puede poseer 1, 2, 3 ó 4 sustituyentes a seleccionar, considerando cada uno en forma independiente, a partir del conjunto que consiste en halógeno, hidroxi, CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, SF₅, -NH₂, C₁₋₆alquilo, C₃₋₆cicloalquilo, C₃₋₆cianocicloalquilo, C₃₋₆halocicloalquilo, C₃₋₆cicloalquilC₁₋₆alquilo, C₁₋₃haloalquilo, C₁₋₃cianoalquilo, C₃₋₆cianocicloalquilo, C₁₋₄alcoxi, C₁₋₃haloalcoxi, C₁₋₃cianoalcoxi, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₁₋₃haloalquiltio, C₁₋₃haloalquilsulfinilo, C₁₋₃haloalquilsulfonilo, C₁₋₃cianoalquiltio, C₁₋₃cianoalquilsulfinilo, C₁₋₃cianoalquilsulfonilo; R³ es hidrógeno o C₁₋₆alquilo opcionalmente sustituido con 1 a 3 sustituyentes a selecciona a partir de halógeno, C₃₋₆-cicloalquilo y C₁₋₆-alcoxi; R⁴ es un heterociclilo monocíclico a seleccionar a partir del conjunto que consiste en un heteroarilo de 5 miembros, un heteroarilo de 6 miembros y un heterociclilo de 3 a 6 miembros, cada uno de los cuales contiene 1 ó 2 heteroátomos a seleccionar a partir del conjunto que consiste en N, O, y S, y cada uno de los cuales opcionalmente está sustituido con 1, 2, 3 ó 4 sustituyentes a seleccionar, considerando cada uno en forma independiente, a partir del conjunto que consiste en halógeno, hidroxi, -CN, -COOH, -NO₂, -NH₂, -SF₅; y C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, C₃₋₆cicloalquilo, C₁₋₆alquil-C₃₋₆cicloalquilo, C₁₋₆haloalquilo, C₃₋₆halocicloalquilo, C₁₋₆alcoxi, C₃₋₆cicloalcoxi, C₁₋₆haloalcoxi, hidroxi-C₁₋₆alquilo, -NH(C₁₋₆alquil), -NH(C₁₋₆alquil-C₃₋₆cicloalquil), -N(C₁₋₆alquil)₂, -N(C₁₋₆alquil)(C₁₋₆alquil-C₃₋₆cicloalquil), -CO₂C₁₋₆alquilo, S-C₁₋₆alquil-sulfinimidoilo, S-C₃₋₆cicloalquil-sulfinimidoilo, S-C₂₋₆alquenil-sulfinimidoilo, S-C₂₋₆alquinil-sulfinimidoilo, S-fenil-sulfinimidoilo, S-heterociclil-sulfinimidoilo, S-heteroaril-sulfinimidoilo, S-C₁₋₆alquil-sulfonimidoilo, S-C₃₋₆cicloalquil-sulfonimidoilo, S-C₂₋₆alquenil-sulfonimidoilo, S-C₂₋₆alquinil-sulfonimidoilo, S-fenil-sulfonimidoilo, S-heterociclil-sulfonimidoilo, S-heteroaril-sulfonimidoilo, -C(=NOC₁₋₆alquil)H, -C(=NOC₁₋₆alquil)-C₁₋₆alquilo, cada uno de los cuales opcionalmente puede estar sustituido; y heterociclilo de 3 a 6 miembros que contiene 1 ó 2 heteroátomos a seleccionar a partir del conjunto que consiste en N, O, y S, siendo que el heterociclilo de 3 a 6 miembros sustituyente opcionalmente puede poseer 1, 2, 3 ó 4 sustituyentes a seleccionar, considerando cada uno en forma independiente, a partir del conjunto que consiste en halógeno, hidroxi, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, -SF₅, -NH₂, C₁₋₆alquilo, C₃₋₆cicloalquilo, C₃₋₆cianocicloalquilo, C₃₋₆halocicloalquilo, C₃₋₆cicloalquilC₁₋₆alquilo, C₁₋₃haloalquilo, C₁₋₃cianoalquilo, C₁₋₄alcoxi, C₁₋₃haloalcoxi, C₁₋₃cianoalcoxi, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₁₋₃haloalquiltio, C₁₋₃haloalquilsulfinilo, C₁₋₃haloalquilsulfonilo, C₁₋₃cianoalquiltio, C₁₋₃cianoalquilsulfinilo, C₁₋₃cianoalquilsulfonilo; y las subestructuras S10 - S18, del grupo de fórmulas (3), en las cuales el enlace al pirazina está marcado con un # y Z es CO o CS y Y considerado en forma independiente se selecciona a partir de CO o SO₂; R⁴¹ es hidrógeno o C₁₋₆alquilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo, -C₁₋₆alquil-C₃₋₆cicloalquilo, fenilo, heteroarilo y heterociclilo, cada uno de los cuales opcionalmente puede estar sustituido; R⁴² es hidrógeno o C₁₋₆alquilo, C₁₋₆haloalquilo y C₃₋₆cicloalquilo, cada uno de los cuales opcionalmente puede estar sustituido; R⁴³ considerado en forma independiente se selecciona a partir de C₁₋₆alquilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo y fenilo, cada uno de los cuales opcionalmente puede estar sustituido; R⁴⁴ en cada caso opcionalmente está sustituido con C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, C₁₋₆haloalquilo, C₃₋₆cicloalquilo, fenilo, heteroarilo y heterociclilo; o R⁴¹ y R⁴² conjuntamente con el átomo de nitrógeno al que están unidos, representan un heterociclilo monocíclico o policíclico de 3 a 12 miembros saturado o insaturado que puede contener otros heteroátomos; R⁵ es hidrógeno, halógeno, -CN, o C₁₋₃alquilo, C₁₋₃haloalquilo, C₁₋₃cianoalquilo, C₃₋₄cicloalquilo, C₃₋₄halocicloalquilo, C₃₋₆cianocicloalquilo, C₁₋₃alcoxi, C₁₋₃haloalcoxi, C₁₋₃cianoalcoxi, -CO₂(C₁₋₃alquil), -CH-(C₁₋₃alcoxi)₂, -CONH(C₁₋₄alquil), -CON(C₁₋₄alquil)₂, -NHCO-C₁₋₄alquilo, -N(C₁₋₄alquil)CO-C₁₋₄alquilo, -C(=NOC₁₋₄alquil)H, o -C(=NOC₁₋₄alquil)-C₁₋₄alquilo, -NH₂, -NH(C₁₋₃alquil), -N(C₁₋₃alquil)₂, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₃₋₆cicloalquiltio, C₃₋₆cicloalquilsulfinilo, C₃₋₆cicloalquilsulfonilo, cada uno de los cuales opcionalmente puede estar sustituido; R⁶ es hidrógeno, halógeno, -CN, o C₁₋₃-alquilo, C₁₋₃-haloalquilo, C₃₋₄cicloalquilo, C₃₋₄halocicloalquilo, C₁₋₃alcoxi, C₁₋₃haloalcoxi, -CO₂(C₁₋₃alquil), -CH-(C₁₋₃alcoxi)₂, -CONH(C₁₋₄alquil), -CON(C₁₋₄alquil)₂, -NHCO-C₁₋₄alquilo, -N(C₁₋₄alquil)CO-C₁₋₄alquilo, -C(=NOC₁₋₄alquil)H, o -C(=NOC₁₋₄alquil)-C₁₋₄alquilo, -NH₂, -NH(C₁₋₃alquil), -N(C₁₋₃alquil)₂, C₁₋₃alquiltio, C₁₋₃alquilsulfinilo, C₁₋₃alquilsulfonilo, C₃₋₆cicloalquiltio, C₃₋₆cicloalquilsulfinilo, C₃₋₆cicloalquilsulfonilo, cada uno de los cuales opcionalmente puede estar sustituido; y sales y N-óxidos de los mismos. Reivindicación 17: Compuestos intermedios conforme a fórmula (4), (5), (6) ó (7), siendo que R³, R⁴, R⁵ y R⁶ poseen el significado que se define en cualquiera de las reivindicaciones 1 a 8.Compounds derived from heteroaryl-pyrazine, intermediates for their preparation and their use for the control of invertebrate pests, in particular insects, arachnids and nematodes, as well as in the field of animal health, that is, in veterinary medicine against endoparasites and ectoparasites. Claim 1: Compounds of the general formula (1), where R¹ is hydrogen; C₁₋₆alkyl, C₃₋₆cycloalkyl, C₃₋₆cycloalkyl, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆haloalkenyl, C₂₋₆alkynyl, C₂₋₆haloalkynyl, each of which may optionally be substituted; or phenyl-C₁₋₆alkyl, in which phenyl is optionally substituted with 1 to 5 substituents, each of which, taken independently, is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, -SF₅, -NH₂, C₁₋₆alkyl, C₃₋₆cycloalkyl, C₃₋₆cyanocycloalkyl, C₃₋₆halocycloalkyl, C₃₋₆cycloalkyl-C₁₁ha₆alkyl,C₋ C₁₋₃cianoalkyl, c₁₋₄alcoxy, c₁₋₃Haloalkoxy, c₁₋₃cianoalcoxy, c₁₋₃alkylthio, c₁₋₃alkylsulfinyl, c₁₋₃alkylsulfonyl, c₁₋₃haloalkylthio, c₁₋₃haloalkylsulfinyl, c₁₋₃Halkylsulfonyl, c₁₋₃cianoalkylthio, c₁₋₃cianoalkylsulfinyl, c₁₋ ₃cyanoalkylsulfonyl; or heterocyclyl-C₁₋₆alkyl, wherein heterocyclyl is selected from the group consisting of saturated or partially unsaturated 3- to 10-membered heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl, and 10-membered heteroaryl and heterocyclyl is optionally substituted with 1 to 5 substituents, each of which, considered independently, is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂ , -Si(CH₃)₃, -SF₅, -NH₂, C₁₋₆alkyl, C₃₋₆cycloalkyl, C₃₋₆cyanocycloalkyl, C₃₋₆halocycloalkyl, C₃₋₆cycloalkyl-C₁₋₆alkyl, C₁₋₃haloalkyl, C₁cyano₋,oxy C₁₋₃haloelcoxy, c₁₋₃cianoalcoxy, c₁₋₃alkylthio, c₁₋₃alkylsulfinyl, c₁₋₃alkylsulfonyl, c₁₋₃haloalkylthio, c₁₋₃haloalkylsulfinyl, c₁₋₃haloalkylsulfonyl, c₁₋₃cianoalkylthio, c₁₋₃cianoalkylsulfinyl, c₁₋₃cianoalkylsulfonyl; R² is phenyl or a 5- or 6-membered heteroaryl, each of which is optionally substituted with 1, 2 or 3 substituents to be selected, each considered independently, from the group consisting of halogen, hydroxy, -CN , -COOH, -NO₂, -NH₂, -SF₅; and c₁₋₆alquyl, C₋₆₋₆alkenyl, C₋₆-alkynyl, c₃₋₆cycloalkyl, c₁₋₆haloalkyl, c₁₋₆alcoxy, c₃₋₆cycloalkoxy, c₁₋₆Halcoxy, hydroxy-c₁₋₆alquyl, -CO₂C₁₋₆alquyl, -NH (c₁₋₆alquil ), -N(C₁₋₆alkyl)₂, S-C₁₋₆alkylsulfinimidoyl, S-C₃₋₆cycloalkylsulfinimidoyl, S-C₂₋₆alkenylsulfinimidoyl, S-C₂₋₆alkynyl-sulfinimidoyl, S-phenyl-sulfinimidoyl, S-heterocyclyl-sulfinimidoyl, -heteroaryl-sulfinimidoyl, S-C₁₋₆alkyl-sulfonimidoyl, S-C₃₋₆cycloalkyl-sulfonimidoyl, S-C₂₋₆alkenyl-sulfonimidoyl, S-C₂₋₆alkynyl-sulfonimidoyl, S-phenyl-sulfonimidoyl, S-heterocyclyl-sulfonimidoyl, S -heteroaryl-sulfonimidoyl, -C(=NOC₁₋₆alkyl)H, -C(=NOC₁₋₆alkyl)-C₁₋₆alkyl, (C₁₋₆alkyl)₃-silyl, each of which may optionally be substituted; and substructures S1-S9, from the group of formulas (2), in which the bond to the 5- or 6-membered phenyl or heteroaryl is marked with a # and Z is CO or CS and Y taken independently is selected from of CO or SO₂; R²¹ is hydrogen or C₁₋₆alkyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl, -C₁₋₆alkyl-C₃₋₆cycloalkyl, phenyl, heteroaryl and heterocyclyl, each of which may optionally be substituted; R²² is hydrogen or C₁₋₆alkyl, C₁₋₆haloalkyl, -C₁₋₆alkyl-C₃₋₆cycloalkyl, and C₃₋₆cycloalkyl, each of which may optionally be substituted; R²³ taken independently is selected from C₁₋₆alkyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl and phenyl, each of which may optionally be substituted; R²⁴ in each occurrence is optionally substituted with C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl, phenyl, heteroaryl and heterocyclyl; or R¹ and R²² together with the nitrogen atom to which they are attached, represent a saturated or unsaturated 3- to 12-membered monocyclic or polycyclic heterocyclyl which may contain other heteroatoms; and 3 to 6 membered heterocyclyl or 5 to 6 membered heteroaryl each containing 1 or 2 heteroatoms to be selected from the group consisting of N, O, and S, where 3 to 6 membered heterocyclyl or the 5- to 6-membered heteroaryl substituent may optionally possess 1, 2, 3 or 4 substituents to be selected, each considered independently, from the group consisting of halogen, hydroxy, CN, -COOH, -CONH₂, - CSNH₂, -NO₂, -Si (CH₃) ₃, SF₅, -NH₂, c₁₋₆alkyl, c₃₋₆cycloalkyl, c₃₋₆cynocycloalkyl, c₃₋₆halocycloalkyl, c₃₋₆cyloalkylc₁₋₆alkyl, c₁₋₃Haloalkyl, c₁₋₃cianoalkyl, c₃₋₆cynocycloalkyl , C₁₋₄alcoxy, c₁₋₃haloelcoxy, c₁₋₃cianoalcoxy, c₁₋₃alkylthio, c₁₋₃alkylsulfinyl, c₁₋₃alkylsulfonyl, c₁₋₃Haloalkylthio, c₁₋₃haloalkylsulfinyl, c₁₋₃haloalkylsulfonyl, c₁₋₃cianoalkylthio, c₁₋₃cianoalkylsulfinyl, c₁₋₃cianalkylsulfonyl; R³ is hydrogen or C₁₋₆alkyl optionally substituted with 1 to 3 substituents selected from halogen, C₃₋₆-cycloalkyl and C₁₋₆-alkoxy; R⁴ is a monocyclic heterocyclyl to be selected from the set consisting of a 5-membered heteroaryl, a 6-membered heteroaryl and a 3 to 6-membered heterocyclyl, each containing 1 or 2 heteroatoms to be selected from the set consisting of N, O, and S, and each of which is optionally substituted with 1, 2, 3 or 4 substituents to be selected, each considered independently, from the group consisting of halogen, hydroxy, - CN, -COOH, -NO₂, -NH₂, -SF₅; and c₁₋₆alquyl, C₋₆₋₆alkenyl, C₋₆-alkynyl, c₃₋₆cycloalkyl, c₁₋₆halquilkyl, c₃₋₆halocycloalkyl, c₁₋₆alcoxy, c₃₋₆cycloalkoxy, c₁₋₆Haloxy, hydroxy-c₁₋₆alquyl , -NH(C₁₋₆alkyl), -NH(C₁₋₆alkyl-C₃₋₆cycloalkyl), -N(C₁₋₆alkyl)₂, -N(C₁₋₆alkyl)(C₁₋₆alkyl-C₃₋₆cycloalkyl), -CO₂C₁₋ ₆alkyl, S-C₁₋₆alkyl-sulfinimidoyl, S-C₃₋₆cycloalkyl-sulfinimidoyl, S-C₂₋₆alkenyl-sulfinimidoyl, S-C₂₋₆alkynyl-sulfinimidoyl, S-phenyl-sulfinimidoyl, S-heterocyclyl-sulfinimidoyl, S-heteroaryl- sulfinimidoyl, S-C₁₋₆alkyl-sulfonimidoyl, S-C₃₋₆cycloalkyl-sulfonimidoyl, S-C₂₋₆alkenyl-sulfonimidoyl, S-C₂₋₆alkynyl-sulfonimidoyl, S-phenyl-sulfonimidoyl, S-heterocyclyl-sulfonimidoyl, S-heteroaryl- sulfonimidoyl, -C(=NOC₁₋₆alkyl)H, -C(=NOC₁₋₆alkyl)-C₁₋₆alkyl, each of which may optionally be substituted; and 3 to 6 membered heterocyclyl containing 1 or 2 heteroatoms to be selected from the group consisting of N, O, and S, wherein the substituent 3 to 6 membered heterocyclyl may optionally possess 1, 2, 3 or 4 substituents to be selected, considering each independently, from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH₂, -CSNH₂, -NO₂, -Si(CH₃)₃, -SF₅, -NH₂, C₁ ₋₆alkyl, c₃₋₆cycloalkyl, c₃₋₆cynocycloalkyl, c₃₋₆halocycloalkyl, c₃₋₆cyloalkylc₁₋₆alquyl, c₁₋₃Haloalkyl, c₁₋₃cianoalkyl, c₁₋₄alcoxy, c₁₋₃Halcoxy, c₁₋₃cianoalcoxy, c₁₋₃alkylthio, c₁₋₃alkylsulfinyl, c₁ ₋₃alkylsulfonyl, C₁₋₃haloalkylthio, C₁₋₃haloalkylsulfinyl, C₁₋₃haloalkylsulfonyl, C₁₋₃cyanoalkylthio, C₁₋₃cyanoalkylsulfinyl, C₁₋₃cyanoalkylsulfonyl; and substructures S10-S18, from the group of formulas (3), in which the pyrazine bond is marked with a # and Z is CO or CS and Y taken independently is selected from CO or SO₂; R⁴¹ is hydrogen or C₁₋₆alkyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl, -C₁₋₆alkyl-C₃₋₆cycloalkyl, phenyl, heteroaryl and heterocyclyl, each of which may optionally be substituted; R⁴² is hydrogen or C₁₋₆alkyl, C₁₋₆haloalkyl, and C₃₋₆cycloalkyl, each of which may optionally be substituted; R⁴³ taken independently is selected from C₁₋₆alkyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl and phenyl, each of which may optionally be substituted; R⁴⁴ in each occurrence is optionally substituted with C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, C₁₋₆haloalkyl, C₃₋₆cycloalkyl, phenyl, heteroaryl and heterocyclyl; or R⁴¹ and R⁴² together with the nitrogen atom to which they are attached, represent a saturated or unsaturated 3- to 12-membered monocyclic or polycyclic heterocyclyl which may contain other heteroatoms; R⁵ is hydrogen, halogen, -cn, or c₁₋₃alquyl, c₁₋₃haloalkyl, c₁₋₃cianoalkyl, c₃₋₄cycloalkyl, c₃₋₄halocycloalkyl, c₃₋₆cynocycloalkyl, c₁₋₃alcoxy, c₁₋₃haloalkoxy, c₁₋₃cianoalcoxy, -CO₂ (c₁ ₋₃alkyl), -CH-(C₁₋₃alkoxy)₂, -CONH(C₁₋₄alkyl), -CON(C₁₋₄alkyl)₂, -NHCO-C₁₋₄alkyl, -N(C₁₋₄alkyl)CO-C₁₋₄alkyl , -C(=NOC₁₋₄alkyl)H, or -C(=NOC₁₋₄alkyl)-C₁₋₄alkyl, -NH₂, -NH(C₁₋₃alkyl), -N(C₁₋₃alkyl)₂, C₁₋₃alkylthio, C₁ ₋₃alkylsulfinyl, C₁₋₃alkylsulfonyl, C₃₋₆cycloalkylthio, C₃₋₆cycloalkylsulfinyl, C₃₋₆cycloalkylsulfonyl, each of which may optionally be substituted; R⁶ is hydrogen, halogen, -CN, or C₁₋₃-alkyl, C₁₋₃-haloalkyl, C₃₋₄cycloalkyl, C₃₋₄halocycloalkyl, C₁₋₃alkoxy, C₁₋₃haloalkoxy, -CO₂(C₁₋₃alkyl), -CH-( C₁₋₃alkoxy)₂, -CONH(C₁₋₄alkyl), -CON(C₁₋₄alkyl)₂, -NHCO-C₁₋₄alkyl, -N(C₁₋₄alkyl)CO-C₁₋₄alkyl, -C(=NOC₁₋₄alkyl )H, or -C(=NOC₁₋₄alkyl)-C₁₋₄alkyl, -NH₂, -NH(C₁₋₃alkyl), -N(C₁₋₃alkyl)₂, C₁₋₃alkylthio, C₁₋₃alkylsulfinyl, C₁₋₃alkylsulfonyl, C₃ ₋₆cycloalkylthio, C₃₋₆cycloalkylsulfinyl, C₃₋₆cycloalkylsulfonyl, each of which may optionally be substituted; and salts and N-oxides thereof. Claim 17: Intermediate compounds according to formula (4), (5), (6) or (7), where R³, R⁴, R⁵ and R⁶ have the meaning defined in any of claims 1 to 8.

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