Fused bicyclic heterocycle derivatives as pesticides
The invention relates to novel compounds of the formula (I) or (I′) in which R 1 , R 2 , R 3 , Aa, Ab, Ac, Ad, Ae, Q and n have the definitions given above, to the use thereof as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for the preparation thereof.
1. A compound of formula (I) or (I′)
wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is nitrogen or ═C(H)—,
Ac is nitrogen or ═C(H)—,
Ad is nitrogen or ═C(H)—,
Ae is nitrogen or ═C(H)—,
where Ab, Ac, Ad and Ae cannot all be nitrogen,
R 1 is (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkenyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkynyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkynyl, (C 2 -C 6 )cyanoalkynyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, amino, (C 1 -C 6 )alkylamino, di-(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylamino, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )alkylsulphinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )haloalkylsulphinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkylsulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkylcarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxycarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonylamino, aminosulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylaminosulphonyl-(C 1 -C 6 )alkyl, di-(C 1 -C 6 )alkylaminosulphonyl-(C 1 -C 6 )alkyl,
or (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 8 )cycloalkyl, each optionally mono- or polysubstituted identically or differently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally be mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, aminosulphonyl, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )alkylsulphimino, (C 1 -C 6 )alkylsulphimino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphimino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylsulphoximino, (C 1 -C 6 )alkylsulphoximino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphoximino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkylcarbonyl, (C 3 -C 6 )trialkylsilyl or benzyl, or
R 1 is aryl, hetaryl or heterocyclyl, each mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )alkylsulphimino, (C 1 -C 6 )alkylsulphimino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphimino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylsulphoximino, (C 1 -C 6 )alkylsulphoximino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphoximino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkylcarbonyl, (C 3 -C 6 )trialkylsilyl, (═O) (in the case of heterocyclyl only) and (═O) 2 (in the case of heterocyclyl only),
R 2 , R 3 are independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri(C 1 -C 6 )alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, hydroxycarbonyl-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkynyl, (C 2 -C 6 )cyanoalkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )cyanoalkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylhydroxyimino, (C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkyl-(C 1 -C 6 )alkoxyimino, (C 1 -C 6 )haloalkyl-(C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )haloalkylsulphinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )haloalkylsulphonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )alkylsulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyloxy, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylthiocarbonyl, (C 1 -C 6 )haloalkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 2 -C 6 )alkenylaminocarbonyl, di-(C 2 -C 6 )-alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 )alkylsulphonylamino, (C 1 -C 6 )alkylamino, di-(C 1 -C 6 )alkylamino, aminosulphonyl, (C 1 -C 6 )alkylaminosulphonyl, di-(C 1 -C 6 )alkylaminosulphonyl, (C 1 -C 6 )alkylsulphoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino or NHCO—(C 1 -C 6 )alkyl ((C 1 -C 6 )alkylcarbonylamino),
R 7 is hydrogen, cyano, halogen, acetyl, hydroxyl, amino, (C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )haloalkylsulphinyl, (C 1 -C 6 )alkylsulphonyl or (C 1 -C 6 )haloalkylsulphonyl,
Q is a partly saturated or saturated heterocyclic or heteroaromatic 8-, 9-, 10-, 11- or 12-membered fused bicyclic or tricyclic ring system, where at least one carbonyl group may optionally be present and/or where the ring system is optionally mono- or polysubstituted identically or differently, and where the substituents may independently be selected from hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri(C 1 -C 6 )alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, hydroxycarbonyl-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy-(C 1 -C 4 )alkyl, (C 2 -C 6 )haloalkynyl, (C 2 -C 6 )cyanoalkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkenyloxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )cyanoalkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylhydroxyimino, (C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkyl-(C 1 -C 6 )alkoxyimino, (C 1 -C 6 )haloalkyl-(C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )haloalkylsulphinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )haloalkylsulphonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )alkylsulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyloxy, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylthiocarbonyl, (C 1 -C 6 )haloalkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 2 -C 6 )alkenylaminocarbonyl, di-(C 2 -C 6 )-alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 )alkylsulphonylamino, (C 1 -C 6 )alkylamino, di-(C 1 -C 6 )alkylamino, aminosulphonyl, (C 1 -C 6 )alkylaminosulphonyl, di-(C 1 -C 6 )alkylaminosulphonyl, (C 1 -C 6 )alkylsulphoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino, NHCO—(C 1 -C 6 )alkyl ((C 1 -C 6 )alkylcarbonylamino),
or where the substituents may independently be selected from phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted identically or differently by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy,
n is 0, 1 or 2,
where, in the case of the structural unit A4, Q is none of the following ring systems:
where X and Y, which may be the same or different, are carbon or nitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R a , with the proviso that X is carbon, where R a is C 1 -C 6 -alkyl, R′ and R″, which may be the same or different, are hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,
and, in addition, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, or Q17;
with the proviso that the compound of formula (I) or (I′) is not
2. The compound of formula (I) or (I′) according to claim 1 , wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is nitrogen or ═C(H)—,
Ac is nitrogen or ═C(H)—,
Ad is nitrogen or ═C(H)—,
Ae is nitrogen or ═C(H)—,
where Ab, Ac, Ad and Ae cannot all be nitrogen,
optionally resulting in one of the following structural units A1 to A44:
where the bond to the substituent Q is identified by a wavy line and the bond to the sulphur atom by an asterisk *,
R 1 is (C 1 -C 4 )alkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkenyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkenyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )alkynyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkynyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkynyl, (C 2 -C 4 )cyanoalkynyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkylamino, di-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkylsulphinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkylcarbonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphonylamino,
or is (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl, each optionally mono- or disubstituted identically or differently by aryl, hetaryl and heterocyclyl, where aryl, hetaryl and heterocyclyl may each optionally be mono- or disubstituted identically or differently by halogen, cyano, carbamoyl, aminosulphonyl, (C 1 -C 4 )-alkyl, (C 3 -C 4 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )alkylsulphimino, or
R 1 is optionally aryl, hetaryl or heterocyclyl, each optionally mono- or disubstituted identically or differently by halogen, cyano, carbamoyl, (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )alkylsulphimino, (C 1 -C 4 )alkylsulphoximino, (C 1 -C 4 )alkylcarbonyl, (C 3 -C 4 )trialkylsilyl, (═O) (in the case of heterocyclyl only) or (═O) 2 (in the case of heterocyclyl only),
R 2 , R 3 are independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri(C 1 -C 4 )alkylsilyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 2 -C 4 )cyanoalkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )cyanoalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylhydroxyimino, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkyl-(C 1 -C 4 )alkoxyimino, (C 1 -C 4 )haloalkyl-(C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )haloalkylsulphinyl, (C 1 -C 4 )alkylsulphinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )haloalkylsulphonyl, (C 1 -C 4 )alkylsulphonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di-(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulphonylamino, (C 1 -C 4 )alkylamino, di-(C 1 -C 4 )alkylamino, aminosulphonyl, (C 1 -C 4 )alkylaminosulphonyl, di-(C 1 -C 4 )alkylaminosulphonyl, aminothiocarbonyl or NHCO—(C 1 -C 4 )alkyl ((C 1 -C 4 )alkylcarbonylamino),
R 7 is hydrogen, cyano, halogen, acetyl, hydroxyl, amino, (C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )haloalkylsulphinyl, (C 1 -C 4 )alkylsulphonyl or (C 1 -C 4 )haloalkylsulphonyl,
Q is a heteroaromatic 8-, 9-, 10-, 11- or 12-membered fused bicyclic or tricyclic ring system, where the ring system is optionally mono- or polysubstituted identically or differently, and where the substituents may independently be selected from hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri-(C 1 -C 6 )alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy-(C 1 -C 4 )alkyl, (C 2 -C 6 )haloalkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyloxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )haloalkenyloxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )cyanoalkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylhydroxyimino, (C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkyl-(C 1 -C 6 )alkoxyimino, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )haloalkylsulphinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )haloalkylsulphonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulphonyl, (C 1 -C 6 )alkylsulphonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulphonyloxy, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylthiocarbonyl, (C 1 -C 6 )haloalkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 )alkylsulphonylamino, (C 1 -C 6 )alkylamino, di-(C 1 -C 6 )alkylamino, aminosulphonyl, (C 1 -C 6 )alkylaminosulphonyl, di-(C 1 -C 6 )alkylaminosulphonyl, (C 1 -C 6 )alkylsulphoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di-(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino, NHCO—(C 1 -C 6 )alkyl ((C 1 -C 6 )alkylcarbonylamino),
or where the substituents may independently be selected from phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted identically or differently by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy,
n is 0, 1 or 2,
where, in the case of the structural unit A4, Q is none of the following ring systems:
where X and Y, which may be the same or different, are carbon or nitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R a , with the proviso that X is carbon, where R a is C 1 -C 6 -alkyl, R′ and R″, which may be the same or different, are hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,
and, in addition, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, or Q17.
3. The compound of formula (I) or (I′) according to claim 1 , wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is nitrogen or ═C(H)—,
Ac is nitrogen or ═C(H)—,
Ad is nitrogen or ═C(H)—,
Ae is nitrogen or ═C(H)—,
where Ab, Ac, Ad and Ae cannot all be nitrogen,
optionally resulting in one of the following structural units: A1, A2, A3, A4, A5, A7, A8, A9, A10, A11, A12, A13, A14, A15, A17, A19, A20, A21, A22, A23, A24, A25, A26, A27, A29, A30, A31, A32, A33, A34, A35, A36, A37, A39, A41, A42, A43, or A44,
R 1 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphinyl-(C 1 -C 4 )alkyl or (C 1 -C 4 )alkylsulphonyl-(C 1 -C 4 )alkyl,
R 2 , R 3 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, SCN, tri-(C 1 -C 4 )alkylsilyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 2 -C 4 )cyanoalkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )cyanoalkoxy, (C 1 -C 4 )alkylhydroxyimino, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkyl-(C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )haloalkylsulphinyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )haloalkylsulphonyl, (C 1 -C 4 )alkylsulphonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di-(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulphonylamino, (C 1 -C 4 )alkylamino, di-(C 1 -C 4 )alkylamino, aminosulphonyl, (C 1 -C 4 )alkylaminosulphonyl, di-(C 1 -C 4 )alkylaminosulphonyl or NHCO—(C 1 -C 4 )alkyl ((C 1 -C 4 )alkylcarbonylamino),
R 7 is hydrogen, halogen, cyano, (C 1 -C 4 )alkyl or (C 1 -C 4 )haloalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system selected from the group consisting of Q1 to Q20
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkenyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkenyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )alkynyloxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )haloalkynyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulphonyl-(C 1 -C 4 )alkyl or (C 1 -C 4 )alkylcarbonyl-(C 1 -C 4 )alkyl,
R 5 , R 6 are independently hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )haloalkylsulphinyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )haloalkylsulphonyl, (C 1 -C 4 )alkylsulphonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di-(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulphonylamino, (C 1 -C 4 )alkylamino, di-(C 1 -C 4 )alkylamino, aminosulphonyl, (C 1 -C 4 )alkylaminosulphonyl or di-(C 1 -C 4 )alkylaminosulphonyl,
n is 0, 1 or 2,
where, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, or Q17.
4. The compound of formula (I) or (I′) according to claim 1 , wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is nitrogen or ═C(H)—,
Ac is nitrogen or ═C(H)—,
Ad is nitrogen or ═C(H)—,
Ae is nitrogen or ═C(H)—,
where Ab, Ac, Ad and Ae cannot all be nitrogen,
optionally resulting in one of the following structural units: A1, A2, A4, A5, A7, A9, A11, A12, A13, A19, A20, A21, A22, A23, A24, A26, A27, A29, A31, A33, A34, A35, A41, A42, A43, or A44,
R 1 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 3 -C 6 )-cycloalkyl,
R 2 , R 3 are independently hydrogen, cyano, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulphinyl, (C 1 -C 4 )-alkylsulphonyl, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-haloalkylsulphinyl, (C 1 -C 4 )-haloalkylsulphonyl or NHCO—(C 1 -C 4 )-alkyl ((C 1 -C 4 )-alkylcarbonylamino),
R 7 is hydrogen, halogen, cyano, (C 1 -C 4 )alkyl or (C 1 -C 4 )haloalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system selected from the group consisting of Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q10, Q11, Q12, Q13, Q15, Q16, Q17, Q18, Q19 and Q20,
R 4 is hydrogen, (C 1 -C 4 )alkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )alkyl,
R 5 is hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulphinyl, (C 1 -C 4 )haloalkylsulphinyl, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )haloalkylsulphonyl, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di-(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulphonylamino, (C 1 -C 4 )alkylaminosulphonyl or di-(C 1 -C 4 )alkylaminosulphonyl,
R 6 is hydrogen,
n is 0, 1 or 2,
where, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q10, Q15, or Q17.
5. The compound of the formula (I) or (I′) according to claim 1 , wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is ═C(H)—,
Ac is ═C(H)—,
Ad is ═C(H)—,
Ae is nitrogen or ═C(H)—,
resulting in one of the following structural units: A1, A4, A23, A26, or A33,
R 1 is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 2 , R 3 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
R 7 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl or trifluoromethyl,
Q is a heteroaromatic 9-membered fused bicyclic ring system selected from the group consisting of Q1, Q2, Q3, Q16, Q17 and Q20,
R 4 is hydrogen, methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl,
R 5 is fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphanyl,
R 6 is hydrogen,
n is 0, 1 or 2,
where, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, or Q17.
6. The compound of formula (I) or (I′) according to claim 1 , wherein
Aa is nitrogen or ═C(R 7 )—,
Ab is ═C(H)—,
Ac is ═C(H)—,
Ad is ═C(H)—,
Ae is nitrogen or ═C(H)—,
resulting in one of the following structural units: A1, A4, A23, A26, or A33
R 1 is methyl or ethyl,
R 2 is hydrogen, chlorine, methoxy or trifluoromethyl,
R 3 is hydrogen,
R 7 is hydrogen,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic ring system selected from the group consisting of Q1, Q2, Q3, Q16, Q17, and Q20,
R 4 is hydrogen or methyl,
R 5 is trifluoromethyl or pentafluoroethyl,
R 6 is hydrogen,
n is 0, 1 or 2,
where, when Aa is ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3, or Q17.
7. The compound of the formula (I′) according to claim 1 .
8. The compound of formula (I) or (I′) according to claim 1 , selected from the group consisting of I-3, I-4, I-6, I-7, I-8, I-9, I-10, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-23, I-24, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-40, I-41, I′-42, I′-43, I′-44, I′-45, I′-47, I′-48, I′-49, I′-50, I′-51, I′-52, I′-53, I′-54, I-55, I-56, I-57, I′-58, I-59,
9. A compound of formula (III-1)
10. The compound of formula (I′) according to claim 7 , wherein Q is
11. The compound of formula (I′) according to claim 7 , wherein n is 2.
12. The compound of formula (I′) according to claim 7 , wherein R 1 is ethyl.
13. The compound of formula (I′) according to claim 7 , wherein R 4 is methyl.
14. The compound of formula (I′) according to claim 7 , wherein
Aa is ═C(R 7 )—, and
R 7 is hydrogen.
15. The compound of formula (I′) according to claim 7 , wherein Ab, Ac, Ad, and Ae are each ═C(H)—.
16. An agrochemical formulation comprising one or more compounds of formula (I) or formula (I′) according to claim 1 and also one or more extenders and/or surfactants.
17. The agrochemical formulation according to claim 16 , additionally comprising a further active agrochemical ingredient.
18. A method for controlling one or more animal pests, comprising allowing a compound of formula (I) or formula (I′) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.
19. A product comprising the compound of formula (I) or formula (I′) according to claim 1 or an agrochemical formulation thereof for controlling one or more animal pests.