Alkylamide substituted, annulated imidazoles and use thereof as insecticides

A compound of general formula (I)

• in which
• X is O or S;
• A1 is N or CR5;
• A2 is N or CR5;
• A3 is N or CR5;
• A4 is N or CR5;
• wherein at least one or two of A1, A2, A3, A4 represents a nitrogen (N);
• R1 is hydrogen;
• or in each case optionally substituted C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl;
• or phenyl-C1-C6 alkyl, 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-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl;
• or
• heterocyclyl-C1-C6 alkyl, wherein the heterocyclyl is selected from the group consisting of saturated and 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-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl;
• 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, —SO2NH2, —SF5;
• and in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, hydroxy-C1-C6 alkyl, —CO2C1-C6 alkyl, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, S—C1-C6 alkylsulfinimidoyl, S—C3-C6 cycloalkylsulfinimidoyl, S—C2-C6 alkenylsulfinimidoyl, S—C2-C6 alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C1-C6 alkylsulfonimidoyl, S—C3-C6 cycloalkylsulfonimidoyl, S—C2-C6 alkenylsulfonimidoyl, S—C2-C6 alkinylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6 alkyl)H, —C(═NOC1-C6 alkyl)-C1-C6 alkyl, and (C1-C6 alkyl)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 and SO2;
• wherein
• R21 is hydrogen or in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, —C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl;
• R22 is hydrogen or in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, —C1-C6 alkyl-C3-C6 cycloalkyl and C3-C6 cycloalkyl;
• R23 is independently selected from in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl and phenyl;
• R24 is in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 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-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl;
• R3 is hydrogen, or C1-C6 alkyl optionally substituted with 1 to 3 substituents selected from halogen, —CN, C3-C6-cycloalkyl and C1-C6-alkoxy;
• R4 is a monocyclic heterocycle selected from the group consisting of a 5-membered heteroaryl and a 6-membered heteroaryl 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;
• and in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, —C1-C6 alkyl-C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, C1-C6 cyanoalkoxy, hydroxy-C1-C6 alkyl, —NH(C1-C6 alkyl), —NH(C1-C6 alkyl-C3-C6 cycloalkyl), —N(C1-C6 alkyl)2, —N(C1-C6 alkyl)(C1-C6 alkyl-C3-C6 cycloalkyl), —CO2C1-C6 alkyl, S—C1-C6 alkylsulfinimidoyl, S—C3-C6 cycloalkylsulfinimidoyl, S—C2-C6 alkenylsulfinimidoyl, S—C2-C6 alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C1-C6 alkylsulfonimidoyl, S—C3-C6 cycloalkylsulfonimidoyl, S—C2-C6 alkenylsulfonimidoyl, S—C2-C6 alkinylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6 alkyl)H, and —C(═NOC1-C6 alkyl)-C1-C6 alkyl;
• and 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-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl;
• and the following substructures S10-S18, in which the bond to the 5-membered heteroaryl and a 6-membered heteroaryl is marked with a # and Z is CO or CS and Y is independently selected from CO and SO2:
• wherein
• R41 is hydrogen or in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, —C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl;
• R42 is hydrogen or in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, —C1-C6 alkyl-C3-C6 cycloalkyl, or C3-C6 cycloalkyl;
• R43 is independently selected from in each case optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl and phenyl;
• R44 is in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 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, —NH2, or in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C1-C3 cyanoalkyl, C3-C4-cycloalkyl, C3-C4 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, —CO2(C1-C3 alkyl), —CH—(C1-C3 alkoxy)2, —CONH(C1-C4 alkyl), —CON(C1-C4 alkyl)2, —NHCO—C1—C4 alkyl, —N(C1-C4 alkyl)CO—C1-C4 alkyl, —C(═NOC1-C4 alkyl)H, —C(═NOC1-C4 alkyl)-C1-C4 alkyl, —NH(C1-C3 alkyl), —N(C1-C3 alkyl)2, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, or C3-C6 cycloalkylsulfonyl;
• and salts and N-oxides thereof.