2-[3-(alkylsulfonyl)-2H-indazol-2-yl]-3H-imidazo[4,5-B]pyridine derivatives and similar compounds as pesticides
The invention relates to compounds of the formula (Ia) or (Ib), in which Aa, Ab, Ac, Ad, R 1 , R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , Q, R4, R 5 , R 6 and have the meanings indicated in the claims, and to agrochemical formulations containing the compounds according to formula (Ia) or (Ib) for use as acaricides and/or insecticides for combating animal pests, primarily arthropods and in particular insects and arachnids. 2-[3-(alkylsulfonyl)-2H-indazol-2-yl]-3H-imidazo[4,5-b]pyridine derivatives and similar compounds are particularly preferable.
1. A compound of formula (Ia) or (Ib)
where represent single bonds or double bonds,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is nitrogen or C(R 10 ),
Ab is nitrogen or C(R 11 ),
Ac is nitrogen or C(R 12 ), and
Ad is nitrogen or C(R 13 ),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R 11 )(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ),
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 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkylsulfonyl-(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 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfonyl-(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 )alkyl sulfonylamino, aminosulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylaminosulfonyl-(C 1 -C 6 )alkyl, di(C 1 -C 6 )alkylaminosulfonyl-(C 1 -C 6 )alkyl,
or is in each case singly or multiply, identically or differently aryl-, hetaryl- or heterocyclyl-substituted (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, where aryl, hetaryl or heterocyclyl may each optionally be mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, aminosulfonyl, (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 )alkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfimino, (C 1 -C 6 )alkylsulfimino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfimino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylsulfoximino, (C 1 -C 6 )alkylsulfoximino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfoximino-(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 optionally 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 )alkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfimino, (C 1 -C 6 )alkylsulfimino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfimino-(C 2 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylsulfoximino, (C 1 -C 6 )alkylsulfoximino-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfoximino-(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) or (═O) 2 (in the case of heterocyclyl only),
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, 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 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )haloalkylsulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyloxy, (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 )alkylsulfonylamino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, aminosulfonyl, (C 1 -C 6 )alkylaminosulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, (C 1 -C 6 )alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino, (C 1 -C 6 )alkylcarbamoyl (including —NHCOO(C 1 -C 6 )alkyl, —N(C 1 -C 6 )alkylCOO(C 1 -C 6 )alkyl, —OCONH(C 1 -C 6 )alkyl or —OCON(C 1 -C 6 )dialkyl), (C 1 -C 6 )alkylcarbonylamino ((C 1 -C 6 )alkylCONH), (C 1 -C 6 )alkylurea (including —NHCONH(C 1 -C 6 )alkyl, and —NHCON(C 1 -C 6 )dialkyl) or
is in each case optionally singly or multiply, identically or differently substituted aryl or hetaryl, where (in the case of hetaryl) at least one carbonyl group may optionally be present and where possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, hydroxyl, amino, 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 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )haloalkylsulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyloxy, (C 1 -C 6 )alkylcarbonyl, (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, di(C 1 -C 6 )alkylaminocarbonyl, (C 2 -C 6 )alkenylaminocarbonyl, di(C 2 -C 6 )-alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 )alkylsulfonylamino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, aminosulfonyl, (C 1 -C 6 )alkylaminosulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, (C 1 -C 6 )alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino or (C 1 -C 6 )alkylcarbonylamino,
where only one or two of the R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 radicals are a substituent other than hydrogen,
and, if any of R 10 and R 14 , R 11 and R 15 , R 12 and R 16 or R 13 and R 17 are both not hydrogen, R 14 , R 15 , R 16 and R 17 are each independently only cyano, halogen, (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 or (C 1 -C 6 )cyanoalkyl,
Q is a partly saturated or saturated heterocyclic or heteroaromatic 8-, 9-, 11- or 12-membered fused bicyclic or tricyclic ring system, where at least one carbonyl group may optionally be present and where the ring system may optionally be mono- or polysubstituted identically or differently, and where the substituents may independently be selected from cyano, halogen, nitro, hydroxyl, amino, 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 )alkyl sulfinyl, (C 1 -C 6 )haloalkyl sulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl sulfonyl, (C 1 -C 6 )haloalkyl sulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyloxy, (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 )alkyl sulfonylamino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, aminosulfonyl, (C 1 -C 6 )alkylaminosulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, (C 1 -C 6 )alkyl sulfoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di(C 1 -C 6 )alkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylamino or (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.
2. The compound of formula (Ia) or (Ib) according to claim 1 ,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is nitrogen or C(R 10 ),
Ab is nitrogen or C(R 11 ),
Ac is nitrogen or C(R 12 ), and
Ad is nitrogen or C(R 13 ),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R 11 )(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ),
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 )alkylsulfinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkylsulfinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyl-(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 or (C 1 -C 4 )alkylsulfonylamino,
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, 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 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylsulfonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, aminothiocarbonyl, (C 1 -C 4 )alkylcarbamoyl (including —NHCOO(C 1 -C 4 )alkyl, —N(C 1 -C 4 )alkylCOO(C 1 -C 4 )alkyl, —OCONH(C 1 -C 4 )alkyl or —OCON(C 1 -C 4 )dialkyl), (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )alkylurea (including —NHCONH(C 1 -C 4 )alkyl, and —NHCON(C 1 -C 4 )dialkyl)
or are phenyl or hetaryl, each of which is optionally mono- or disubstituted identically or differently, where (in the case of hetaryl) at least one carbonyl group may optionally be present and where possible substituents are in each case as follows: cyano, halogen, nitro, acetyl, amino, (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 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylsulfonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyloxy, (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 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl or (C 1 -C 4 )alkylcarbonylamino,
where only one or two of the R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 radicals are a substituent other than hydrogen,
and, if any of R 10 and R 14 , R 11 and R 15 , R 12 and R 16 or R 13 and R 17 are both not hydrogen, R 14 , R 15 , R 16 and R 17 are each independently only cyano, halogen, (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 or (C 1 -C 4 )cyanoalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q15:
where
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 )haloalkynyl or (C 3 -C 6 )cycloalkyl and
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 )haloalkyl-(C 3 -C 6 )cycloalkyl, cyano-(C 3 -C 6 )cycloalkyl, halo-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )haloalkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylsulfonyloxy, (C 1 -C 4 )haloalkylsulfonyloxy, (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 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl or di(C 1 -C 4 )alkylaminosulfonyl
and
n is 0, 1 or 2.
3. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is nitrogen or C(R 10 ),
Ab is nitrogen or C(R 11 ),
Ac is nitrogen or C(R 12 ), and
Ad is nitrogen or C(R 13 ),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R)(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ),
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 )alkylsulfinyl-(C 1 -C 4 )alkyl or (C 1 -C 4 )alkylsulfonyl-(C 1 -C 4 )alkyl,
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, 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 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkyl sulfonyl, (C 1 -C 4 )alkylsulfonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, (C 1 -C 4 )alkylcarbamoyl (including —NHCOO(C 1 -C 4 )alkyl and —N(C 1 -C 4 )alkylCOO(C 1 -C 4 )alkyl), (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )alkylurea (including —NHCONH(C 1 -C 4 )alkyl and —NHCON(C 1 -C 4 )dialkyl) or are phenyl or hetaryl, each of which is optionally mono- or disubstituted identically or differently, where (in the case of hetaryl) at least one carbonyl group may optionally be present and where possible substituents are in each case as follows: cyano, halogen, (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 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 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylsulfonyloxy, (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 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, (C 1 -C 4 )alkylcarbonylamino,
where only one or two of the R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 radicals are a substituent other than hydrogen,
and, if any of R 10 and R 14 , R 11 and R 15 , R 12 and R 16 or R 13 and R 17 are both not hydrogen, R 14 , R 15 , R 16 and R 17 are each independently only cyano, halogen, (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 or (C 1 -C 4 )cyanoalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q15,
where
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (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 )haloalkenyl, (C 2 -C 4 )alkynyl or (C 2 -C 4 )haloalkynyl and
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 )haloalkyl-(C 3 -C 6 )cycloalkyl, cyano-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )haloalkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylsulfonyloxy, (C 1 -C 4 )haloalkylsulfonyloxy, (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 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl or di(C 1 -C 4 )alkylaminosulfonyl
and
n is 0, 1 or 2.
4. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is nitrogen or C(R 10 ),
Ab is nitrogen or C(R 1 ),
Ac is nitrogen or C(R 12 ), and
Ad is nitrogen or C(R 13 ),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R 1 )(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ),
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 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 are independently hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkyl sulfonyl, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )haloalkylsulfonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 )alkylcarbamoyl (including —NHCOO(C 1 -C 4 )alkyl and —N(C 1 -C 4 )alkylCOO(C 1 -C 4 )alkyl), (C 1 -C 4 )alkylcarbonylamino or (C 1 -C 4 )alkylurea (including —NHCONH(C 1 -C 4 )alkyl and —NHCON(C 1 -C 4 )dialkyl),
where only one or two of the R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 radicals are a substituent other than hydrogen,
and, if any of R 10 and R 14 , R 11 and R 15 , R 12 and R 16 or R 13 and R 17 are both not hydrogen, R 14 , R 15 , R 16 and R 17 are each independently only cyano, halogen, (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 from the group of Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q14 or Q15,
where
R 4 is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )cycloalkyl or (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl,
R 5 is cyano, halogen, (C 1 -C 4 )haloalkyl, halo-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )haloalkylcarbonyl or (C 1 -C 4 )haloalkylsulfonyloxy,
R 6 is hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl or (C 3 -C 6 )cycloalkyl and
n is 0, 1 or 2.
5. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is C(R 10 ),
Ab is C(R 11 ),
Ac is C(R 12 ) and
Ad is C(R 13 ),
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R 11 )(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ),
R 1 is ethyl,
R 10 , R 11 , R 12 , R 13 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, acetylamino (methylcarbonylamino), cyclopropylamido (cyclopropylaminocarbonyl), methylcarbamoyl (—NHCOOMe), methylurea (—NHCONHMe) or cyclopropyl,
where only one or two of the R 10 , R 11 , R 12 , R 13 radicals are a substituent other than hydrogen,
R 14 , R 15 , R 16 , R 17 are independently hydrogen or (C 1 -C 4 )alkyl,
Q is a heteroaromatic 9-membered fused bicyclic ring system from the group of Q2, Q3 and Q14
where
R 4 is methyl,
R 5 is trifluoromethyl or pentafluoroethyl,
R 6 is hydrogen and
n is 0, 1 or 2.
6. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which,
if represent exclusively double bonds and hence Aa to Ad together with the carbon atoms adjacent to Aa and Ad in each case form an aromatic ring,
Aa is C(R 10 ),
Ab is nitrogen or C(R 11 ),
Ac is C(R 12 ) and
Ad is C(R 13 ), where
R 10 is hydrogen, chlorine or trifluoromethyl,
R 11 is hydrogen, chlorine, —NHCOMe or trifluoromethyl,
R 12 is hydrogen, chlorine or trifluoromethyl,
R 13 is hydrogen, chlorine or trifluoromethyl,
or, if represent exclusively single bonds,
Aa is C(R 10 )(R 14 ),
Ab is C(R 11 )(R 15 ),
Ac is C(R 12 )(R 16 ) and
Ad is C(R 13 )(R 17 ), where
R 10 , R 12 , R 13 , R 14 , R 16 , R 17 are hydrogen,
R 11 is hydrogen or methyl and
R 15 is hydrogen or methyl,
R 1 is ethyl,
Q is a heteroaromatic 9-membered fused bicyclic ring system from the group of Q2 and Q3
where
R 4 is methyl,
R 5 is trifluoromethyl or pentafluoroethyl,
R 6 is hydrogen and
n is 0, 1 or 2.
7. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which
Q is Q2, Q3, Q5, Q6, Q8, Q9, Q14 or Q15,
where
R 4 is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )cycloalkyl or (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl,
R 5 is cyano, halogen, (C 1 -C 4 )haloalkyl, halo-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )haloalkylcarbonyl or (C 1 -C 4 )haloalkylsulfonyloxy,
R 6 is hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl or (C 3 -C 6 )cycloalkyl and and Aa, Ab, Ac, Ad, R 1 , R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and n have the definitions according to claim 2 .
8. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which
Q is Q2, Q3 or Q14
where
R 4 is methyl,
R 5 is trifluoromethyl or pentafluoroethyl,
R 6 is hydrogen
and Aa, Ab, Ac, Ad, R 1 , R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and n have the definitions according to claim 2 .
9. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which
Q is Q2 or Q3
where
R 4 is methyl,
R 5 is trifluoromethyl or pentafluoroethyl,
R 6 is hydrogen
and Aa, Ab, Ac, Ad, R 1 , R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and n have the definitions according to claim 2 .
10. The compound of formula (Ia) or (Ib) according to claim 2 ,
in which R 1 is ethyl and Aa, Ab, Ac, Ad, R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 Q, R 4 , R 5 , R 6 and n have the definitions according to claim 2 .
11. The compound of formula (Ia) or (Ib) according to claim 2 ,
where the formulae (Ia) and (Ib) give rise to the following structures (Ia1) to (Ia4) and (Ib1)
where R 1 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , Q, R 4 , R 5 , R 6 and n have the definitions described in claim 2 .
12. A compound selected from the group consisting of
13. The compound of formula (Ia) or (Ib) according to claim 1 ,
characterized in that, if for the compound of the formula (Ia)
represents exclusively double bonds,
R 1 is C 1 -C 6 alkyl,
Aa and Ad are CH,
Ab is C(R 11 ),
Ac is C(R 12 )
and
Q is Q2
where
R 4 is C 1 -C 6 alkyl,
R 6 is hydrogen and
R 5 is (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )haloalkylsulfinyl or (C 1 -C 6 )haloalkylsulfonyl,
at least one of the radicals R 11 or R 12 is not hydrogen, halogen or (C 1 -C 6 )haloalkyl.
14. A compound of formulae (Ia) or (Ib) according to claim 1 ,
characterized in that, if for the compound of the formula (Ia)
represents exclusively double bonds,
R 1 is C 1 -C 6 alkyl,
Aa and Ad are CH,
Ab is C(R 11 ),
Ac is C(R 12 )
R 11 and R 12 are independently hydrogen, halogen or (C 1 -C 6 )haloalkyl
and
Q is Q2
where
R 4 is C 1 -C 6 alkyl and
R 6 is hydrogen,
R 5 is not (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )haloalkylsulfinyl or (C 1 -C 6 )haloalkylsulfonyl.
15. The compound of formula (Ia) or (Ib) according to claim 1 , wherein the compound is not a compound of formula (Y)
in which
R 1 is (C 1 -C 6 )alkyl,
R 4 is (C 1 -C 6 )alkyl,
R 5 is (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )haloalkylsulfinyl or (C 1 -C 6 )haloalkylsulfonyl,
R 11 and R 12 are independently each hydrogen, halogen or (C 1 -C 6 ) haloalkyl and
n is 0, 1 or 2.
16. The compound of formula (Ia) according to claim 1 , characterized in that represents exclusively single bonds.
17. An agrochemical formulation comprising at least one compound of formula (Ia) or (Ib) according to claim 1 and also extenders and/or surfactants.
18. The agrochemical formulation according to claim 17 , additionally comprising a further agrochemically active ingredient.
19. A method for controlling animal pests comprising allowing a compound of formula (Ia) or (Ib) according to claim 1 to act on the animal pests and/or their habitat.
20. A method for controlling animal pests comprising allowing an agrochemical formulation according to claim 17 to act on the animal pests and/or their habitat.