Heterocyclic compounds for the control of invertebrate pests

Compounds-A compound of formula I

• wherein
• R1 is H, OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C5-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-halocycloalkyl, which groups are unsubstituted, or partially or fully substituted with R11;
• or C(═N—R11)R12, C(O)R11a;
• R11 is CN, NO2, NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR14, Si(CH3)3;
• C1-C6-alkyl;
• C1-C6-haloalkyl;
• C2-C6-alkenyl;
• C2-C6-haloalkenyl;
• C2-C6-alkynyl;
• C2-C6-haloalkynyl;
• C3-C4-cycloalkyl-C1-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen;
• 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• R11a is NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR14, Si(CH3)3;
• C1-C6-haloalkyl;
• C2-C6-alkenyl;
• C2-C6-haloalkenyl;
• C2-C6-alkynyl;
• C2-C6-haloalkynyl;
• C3-C6-cycloalkyl-C1-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen;
• 3- to 6-membered heterocyclyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• R12, R13 are independently from each other H, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, C(O)—C1-C4-alkyl, C(O)—C1-C4-haloalkyl, C(O)—C3-C4-cycloalkyl, C(O)—C3-C4-halocycloalkyl, C(O)NR121R131, S(O)m—C1-C4-haloalkyl, S(O)m—C3-C6-cycloalkyl, S(O)m—C3-C6-halocycloalkyl;
• 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• R121 and R131 are independently from each other H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy;
• C1-C4-alkyl-phenyl, C1-C4-alkyl-3-6-membered hetaryl, phenyl, 3- to 6-membered heterocyclyl or 5- or 6-membered hetaryl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• or
• R121 and R131 together with the nitrogen atom they are bound to form a 3-6 membered saturated, partially or fully unsaturated heterocycle, which may further contain 1 or 2 heteroatoms ring members selected from N, O and S, wherein S may be oxidized, which heterocycle is unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• or R12 and R13 together with the nitrogen atom they are bound to form a 3-6 membered saturated, partially unsaturated, or aromatic heterocycle, which may contain 1 or 2 additional heteroatoms selected from N, O and S, wherein S may be partially or fully oxidized, and which is unsubstituted or substituted with oxo, and/or R3;
• or R12 and R13 together with the nitrogen atom they are bound to form a group
• N═S(═O)R14aR14b, wherein R14a and R14b are defined as R14;
• m is 0, 1, or 2;
• R14 is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C4-cycloalkyl-C1-C2-alkyl, C3-C4-halocycloalkyl-C1-C2-alkyl, C(O)—C1-C4-alkyl, C(O)—C1-C4-haloalkyl, C(O)—C3-C4-cycloalkyl, C(O)—C3-C4-halocycloalkyl, or phenyl which is unsubstituted or partially or fully substituted with R3;
• R2 is H, CN, C1-C3-alkyl, C1-C3-haloalkyl, C2-C3-alkynyl;
• X is CH, CR3, or N;
• R3 is halogen, CN, NO2, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, OR14, S(O)m—R14;
• which are unsubstituted or substituted with R3a;
• R3a halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, OR15, C1-C4-haloalkoxy, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, S(O)m—C1-C4-alkyl, S(O)m—C1-C4-haloalkyl, S(O)m—C3-C4-cycloalkyl, S(O)m—C3-C4-halocycloalkyl;
• n is 0, 1, 2, or 3;
• R4 is C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, each unsubstituted or partially or fully substituted with R41;
• S(O)m—C1-C4-alkyl, S(O)m—C1-C4-haloalkyl, S(O)m—C3-C6-cyclo-alkyl, S(O)m—C3-C6-halocycloalkyl, NR12R13, C(O)NR12R13, C(O)OR14, 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or partially or fully substituted with R3;
• R41 is H, OR15, NR12R13, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C(O)—C1-C4-alkyl, C(O)—C1-C4-haloalkyl, C(O)—C3-C4-cycloalkyl, C(O)—C3-C4-halocycloalkyl, C(O)OR15,
• C(O)NR121R131;
• S(O)m—C1-C4-haloalkyl, S(O)m—C3-C4-cycloalkyl, S(O)m—C3-C4-halocycloalkyl;
• 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl;
• which cyclic R41 groups are unsubstituted or partially or fully substituted with halogen, C1-C3-haloalkyl, and/or CN;
• R15 is H, C1-C4-alkyl, or C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C6-halocycloalkyl, which carbon chains are unsubstituted or partially or fully substituted with R11;
• or 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or partially or fully substituted with R3;
• R5 is H, halogen, CN, OR15, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-phenyl, C1-C4-alkyl-3-6-membered hetaryl, phenyl, 3- to 6-membered heterocyclyl or 5- or 6-membered hetaryl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN;
• Q, Q1, and Q2 are, independently from each other, N or CR6, wherein no more than one of Q, Q1, and Q2 is N;
• R6 is H, halogen, CN, OR14, NR12R13, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C(O)NR12R13, C(O)OR14, S(O)m—C1-C4-alkyl, S(O)m—C1-C4-haloalkyl, S(O)m—C3-C6-cycloalkyl, S(O)m—C3-C6-halocycloalkyl;
• and N-oxides, stereoisomers, and agriculturally or veterinarily acceptable salts thereof.