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filingDate 2020-10-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 2022-02-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-120183-A1
titleOfInvention HETEROARYL-PYRAZINE COMPOUNDS AS PESTICIDES
abstract 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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