Heteroaryl-substituted pyrazine derivatives as pesticides

A compound of formula (I)

• wherein,
• R1 is hydrogen, in each case optionally substituted C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, or C2-C6haloalkynyl;
• or phenyl-C1-C6alkyl, in which phenyl is optionally substituted with 1 to 5 substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycanocycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C3haloalkyl, C1-C3cyanoalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3cyanoalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, C1-C3cyanoalkylthio, C1-C3cyanoalkylsulfinyl, or C1-C3cyanoalkylsulfonyl;
• or heterocyclyl-C1-C6alkyl, wherein the 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 the heterocyclyl is optionally substituted with 1 to 5 substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycanocycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C6haloalkyl, C1-C3cyanoalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3cyanoalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, C1-C3cyanoalkylthio, C1-C3cyanoalkylsulfinyl, and C1-C3cyanoalkylsulfonyl;
• R2 is phenyl or a 5- or 6-membered heteroaryl, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of
• halogen, hydroxy, —CN, —COOH, —NO2, —NH2, —SF5;
• in each case optionally substituted C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, C3-C6cycloalkoxy, C1-C6haloalkoxy, hydroxy-C1-C6alkyl, —CO2C1-C6alkyl, —NH (C1-C6alkyl), —N(C1-C6alkyl)2, S-C1-C6alkylsulfinimidoyl, S-C3-C6cycloalkylsulfinimidoyl, S-C2-C6alkenylsulfinimidoyl, S-C2-C6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6alkylsulfonimidoyl, S-C3-C6cycloalkylsulfonimidoyl, S-C2-C6alkenylsulfonimidoyl, S-C2-C6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6alkyl) H, —C(═NOC1-C6alkyl)-C1-C6alkyl, (C1-C6alkyl) 3-silyl;
• and the substructures S1-S9, in which the bond to the phenyl or 5- or 6-membered heteroaryl is marked with a # and Z is CO or CS and Y is independently selected from CO or SO2;
• R21 is hydrogen or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, —C1-C6alkyl-C3-C6cycloalkyl, phenyl, heteroaryl or heterocyclyl;
• R22 is hydrogen or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, —C1-C6alkyl-C3-C6cycloalkyl or C3-C6cycloalkyl;
• R23 is independently selected from in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl or phenyl;
• R24 is in each case optionally substituted C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, heteroaryl or heterocyclyl;
• or
• R21 and R22 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or unsaturated heterocyclyl which may contain further heteroatoms;
• and 3- to 6-membered heterocyclyl or a 5- to 6-membered heteroaryl each containing 1 or 2 heteroatoms selected from the group consisting of N, O, and S, wherein the 3- to 6-membered heterocyclyl or the 5- to 6-membered heteroaryl substituent may optionally carry 1, 2, 3 or 4 substituents independently selected from the group consisting of halogen, hydroxy, CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, SF5, —NH2, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycanocycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C3haloalkyl, C1-C3cyanoalkyl, C3-C6cyanocycloalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3cyanoalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, C1-C3cyanoalkylthio, C1-C3cyanoalkylsulfinyl, and C1-C3cyanoalkylsulfonyl;
• R3 is hydrogen or C1-C6alkyl optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C3-C6-cycloalkyl and C1-C6-alkoxy;
• R4 is a monocyclic heterocycle selected from the group consisting of a 5-membered heteroaryl, a 6-membered heteroaryl and a 3-6 membered heterocyclyl, each of which containing 1 or 2 heteroatoms selected from the group consisting of N, O, and S, and each of which is optionally substituted by 1, 2, 3 or 4 substituents independently selected from the group consisting of
• halogen, hydroxy, —CN, —COOH, —NO2, —NH2, —SF5;
• in each case optionally substituted C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6alkyl-C3-C6cycloalkyl, C1-C6haloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C3-C6cycloalkoxy, C1-C6haloalkoxy, hydroxy-C1-C6alkyl, —NH(C1-C6alkyl), —NH(C1-C6alkyl-C3-C6cycloalkyl), —N(C1-C6alkyl)2, —N(C1-C6alkyl) (C1-C6alkyl-C3-C6cycloalkyl), —CO2C1-C6alkyl, S-C1-C6alkylsulfinimidoyl, S-C3-C6cycloalkylsulfinimidoyl, S-C2-C6alkenylsulfinimidoyl, S-C2-C6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6alkylsulfonimidoyl, S-C3-C6cycloalkylsulfonimidoyl, S-C2-C6alkenylsulfonimidoyl, S-C2-C6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6alkyl) H, —C(═NOC1-C6alkyl)-C1-C6alkyl;
• 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from the group consisting of N, O, and S, wherein the 3- to 6-membered heterocyclyl substituent may optionally carry 1, 2, 3 or 4 substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycanocycloalkyl, C3-Chalocycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C3haloalkyl, C1-C3cyanoalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3cyanoalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, C1-C3cyanoalkylthio, C1-C3cyanoalkylsulfinyl, and C1-C3cyanoalkylsulfonyl;
• and the following substructures S10-S18, in which the bond to the 5-membered heteroaryl, the 6-membered heteroaryl or the 3-6 membered heterocyclyl is marked with a # and Z is CO or CS and Y is independently selected from CO or SO2:
• R41 is hydrogen or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, —C1-C6alkyl-C3-C6cycloalkyl, phenyl, heteroaryl or heterocyclyl;
• R42 is hydrogen or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl or C3-C6cycloalkyl;
• R43 is independently selected from in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl or phenyl;
• R44 is in each case optionally substituted C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, heteroaryl or heterocyclyl;
• or
• R41 and R42 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or unsaturated heterocyclyl which may contain further heteroatoms;
• R5 is hydrogen, halogen, —CN, or in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C1-C3cyanoalkyl, C3-C4-cycloalkyl, C3-C4halocycloalkyl, C3-C6cyanocycloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3cyanoalkoxy, —CO2 (C1-C3alkyl), —CH-(C1-C3alkoxy) 2, —CONH(C1-C4alkyl), —CON(C1-C4alkyl)2, —NHCO-C1-C4alkyl, —N(C1-C4alkyl)CO-C1-C4alkyl, —C(═NOC1-C4alkyl) H, or —C(═NOC1-C4alkyl)-C1-C4alkyl, —NH2, —NH(C1-C3alkyl), —N(C1-C3alkyl)2, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, or C3-C6cycloalkylsulfonyl;
• R6 is hydrogen, halogen, —CN, or in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C3-C4cycloalkyl, C3-C4halocycloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, —CO2 (C1-C3alkyl), —CH-(C1-C3alkoxy) 2, —CONH(C1-C4alkyl), —CON(C1-C4alkyl)2, —NHCO-C1-C4alkyl, —N(C1-C4alkyl)CO-C1-C4alkyl, —C(═NOC1-C4alkyl) H, or —C(═NOC1-C4alkyl)-C1-C4alkyl, —NH2, —NH(C1-C3alkyl), —N(C1-C3alkyl)2, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, or C3-C6cycloalkylsulfonyl;
• and/or a salt and/or a N-oxide thereof.