# US 10,765,116 B2 · 2-[3-(alkylsulfonyl)-2H-indazol-2-yl]-3H-imidazo[4,5-B]pyridine derivatives and similar compounds as pesticides

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,765,116 B2
- Document ID: US10765116B2
- Status: Granted
- Kind: B2
- Application number: 16/463,327
- Filed: 2017-11-22
- Published: 2019-09-12
- Granted: 2020-09-08
- Earliest claimed: 2016-11-23
- Assignees: Bayer CropScience AG; Bayer Aktiengesellschaft
- Applicants: Bayer Cropscience Aktiengesellschaft; Bayer Aktiengesellschaft
- Inventors: Nina Kausch-Busies; Rüdiger Fischer; Laura Hoffmeister; David Wilcke; Dominik Hager; Matthieu Willot; Marc Mosrin; Kerstin Ilg; Ulrich Görgens; Andreas Turberg
- Web page: https://patentgrep.com/patent/US10765116B2

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 471/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to compounds of the formula (Ia) or (Ib), in which Aa, Ab, Ac, Ad, R1, R10 R11, R12, R13, R14, R15, R16, R17, Q, R4, R5, R6 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.

## Claims

### Claim 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(R10),
Ab is nitrogen or C(R11),
Ac is nitrogen or C(R12), and
Ad is nitrogen or C(R13),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R11)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17),
R1 is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, (C3-C8)cycloalkylamino, (C1-C6)alkylcarbonylamino, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)haloalkylsulfinyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)haloalkylsulfonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)haloalkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)haloalkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkyl sulfonylamino, aminosulfonyl-(C1-C6)alkyl, (C1-C6)alkylaminosulfonyl-(C1-C6)alkyl, di(C1-C6)alkylaminosulfonyl-(C1-C6)alkyl,
or is in each case singly or multiply, identically or differently aryl-, hetaryl- or heterocyclyl-substituted (C1-C6)alkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)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, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylsulfimino, (C1-C6)alkylsulfimino-(C1-C6)alkyl, (C1-C6)alkylsulfimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulfoximino, (C1-C6)alkylsulfoximino-(C1-C6)alkyl, (C1-C6)alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, (C3-C6)trialkylsilyl or benzyl, or
R1 is aryl, hetaryl or heterocyclyl, each optionally mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C1-C6)-alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylsulfimino, (C1-C6)alkylsulfimino-(C1-C6)alkyl, (C1-C6)alkylsulfimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulfoximino, (C1-C6)alkylsulfoximino-(C1-C6)alkyl, (C1-C6)alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, (C3-C6)trialkylsilyl, (═O) (in the case of heterocyclyl only) or (═O)2 (in the case of heterocyclyl only),
R10, R11, R12, R13, R14, R15, R16, R17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, tri(C1-C6)alkylsilyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, hydroxycarbonyl-(C1-C6)-alkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)cyanoalkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkoxy, (C1-C6)alkylhydroxyimino, (C1-C6)alkoxyimino, (C1-C6)alkyl-(C1-C6)alkoxyimino, (C1-C6)haloalkyl-(C1-C6)alkoxyimino, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkoxy-(C1-C6)alkylthio, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, (C1-C6)alkoxy-(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyloxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylthiocarbonyl, (C1-C6)haloalkylcarbonyl, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkoxycarbonyl, aminocarbonyl, (C1-C6)alkylaminocarbonyl, (C1-C6)alkylaminothiocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, (C2-C6)alkenylaminocarbonyl, di(C2-C6)alkenylaminocarbonyl, (C3-C8)cycloalkylaminocarbonyl, (C1-C6)alkylsulfonylamino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aminosulfonyl, (C1-C6)alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, (C1-C6)alkylsulfoximino, aminothiocarbonyl, (C1-C6)alkylaminothiocarbonyl, di(C1-C6)alkylaminothiocarbonyl, (C3-C8)cycloalkylamino, (C1-C6)alkylcarbamoyl (including —NHCOO(C1-C6)alkyl, —N(C1-C6)alkylCOO(C1-C6)alkyl, —OCONH(C1-C6)alkyl or —OCON(C1-C6)dialkyl), (C1-C6)alkylcarbonylamino ((C1-C6)alkylCONH), (C1-C6)alkylurea (including —NHCONH(C1-C6)alkyl, and —NHCON(C1-C6)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-(C1-C6)alkylsilyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, hydroxycarbonyl-(C1-C6)-alkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)cyanoalkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkoxy, (C1-C6)alkylhydroxyimino, (C1-C6)alkoxyimino, (C1-C6)alkyl-(C1-C6)alkoxyimino, (C1-C6)haloalkyl-(C1-C6)alkoxyimino, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkoxy-(C1-C6)alkylthio, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, (C1-C6)alkoxy-(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyloxy, (C1-C6)alkylcarbonyl, (C1-C6)haloalkylcarbonyl, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkoxycarbonyl, aminocarbonyl, (C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, (C2-C6)alkenylaminocarbonyl, di(C2-C6)-alkenylaminocarbonyl, (C3-C8)cycloalkylaminocarbonyl, (C1-C6)alkylsulfonylamino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aminosulfonyl, (C1-C6)alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, (C1-C6)alkylsulfoximino, aminothiocarbonyl, (C1-C6)alkylaminothiocarbonyl, di(C1-C6)alkylaminothiocarbonyl, (C3-C8)cycloalkylamino or (C1-C6)alkylcarbonylamino,
where only one or two of the R10, R11, R12, R13, R14, R15, R16 and R17 radicals are a substituent other than hydrogen,
and, if any of R10 and R14, R11 and R15, R12 and R16 or R13 and R17 are both not hydrogen, R14, R15, R16 and R17 are each independently only cyano, halogen, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkyl, (C1-C6)haloalkyl or (C1-C6)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(C1-C6)alkylsilyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkyl, C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, hydroxycarbonyl-(C1-C6)-alkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C4)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C1-C6)cyanoalkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkoxy, (C1-C6)alkylhydroxyimino, (C1-C6)alkoxyimino, (C1-C6)alkyl-(C1-C6)alkoxyimino, (C1-C6)haloalkyl-(C1-C6)alkoxyimino, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkoxy-(C1-C6)alkylthio, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkyl sulfinyl, (C1-C6)haloalkyl sulfinyl, (C1-C6)alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)alkyl sulfonyl, (C1-C6)haloalkyl sulfonyl, (C1-C6)alkoxy-(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)alkylsulfonyloxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkylthiocarbonyl, (C1-C6)haloalkylcarbonyl, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkoxycarbonyl, aminocarbonyl, (C1-C6)alkylaminocarbonyl, (C1-C6)alkylaminothiocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, (C2-C6)alkenylaminocarbonyl, di(C2-C6)alkenylaminocarbonyl, (C3-C8)cycloalkylaminocarbonyl, (C1-C6)alkyl sulfonylamino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aminosulfonyl, (C1-C6)alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, (C1-C6)alkyl sulfoximino, aminothiocarbonyl, (C1-C6)alkylaminothiocarbonyl, di(C1-C6)alkylaminothiocarbonyl, (C3-C8)cycloalkylamino or (C1-C6)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 C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, C1-C4-alkoxy, C1-C4-haloalkoxy,
n is 0, 1 or 2.

### Claim 2 (depends on 1)

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(R10),
Ab is nitrogen or C(R11),
Ac is nitrogen or C(R12), and
Ad is nitrogen or C(R13),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R11)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17),
R1 is (C1-C4)alkyl, (C1-C4)hydroxyalkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkenyloxy-(C1-C4)alkyl, (C2-C4)haloalkenyloxy-(C1-C4)alkyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)alkynyloxy-(C1-C4)alkyl, (C2-C4)haloalkynyloxy-(C1-C4)alkyl, (C2-C4)haloalkynyl, (C2-C4)cyanoalkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkylamino, di(C1-C4)alkylamino, (C3-C6)cycloalkylamino, (C1-C4)alkylcarbonylamino, (C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)haloalkylthio-(C1-C4)alkyl, (C1-C4)alkylsulfinyl-(C1-C4)alkyl, (C1-C4)haloalkylsulfinyl-(C1-C4)alkyl, (C1-C4)alkylsulfonyl-(C1-C4)alkyl, (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)haloalkylcarbonyl-(C1-C4)alkyl or (C1-C4)alkylsulfonylamino,
R10, R11, R12, R13, R14, R15, R16, R17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, tri(C1-C4)alkylsilyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C2-C4)cyanoalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)cyanoalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)alkylhydroxyimino, (C1-C4)alkoxyimino, (C1-C4)alkyl-(C1-C4)alkoxyimino, (C1-C4)haloalkyl-(C1-C4)alkoxyimino, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfinyl-(C1-C4)alkyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)alkylsulfonyl-(C1-C4)alkyl, (C1-C4)alkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C3-C6)cycloalkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl, di(C1-C4)alkylaminosulfonyl, aminothiocarbonyl, (C1-C4)alkylcarbamoyl (including —NHCOO(C1-C4)alkyl, —N(C1-C4)alkylCOO(C1-C4)alkyl, —OCONH(C1-C4)alkyl or —OCON(C1-C4)dialkyl), (C1-C4)alkylcarbonylamino, (C1-C4)alkylurea (including —NHCONH(C1-C4)alkyl, and —NHCON(C1-C4)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, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C2-C4)cyanoalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)cyanoalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)alkylhydroxyimino, (C1-C4)alkoxyimino, (C1-C4)alkyl-(C1-C4)alkoxyimino, (C1-C4)haloalkyl-(C1-C4)alkoxyimino, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfinyl-(C1-C4)alkyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)alkylsulfonyl-(C1-C4)alkyl, (C1-C4)alkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl, di(C1-C4)alkylaminosulfonyl or (C1-C4)alkylcarbonylamino,
where only one or two of the R10, R11, R12, R13, R14, R15, R16, R17 radicals are a substituent other than hydrogen,
and, if any of R10 and R14, R11 and R15, R12 and R16 or R13 and R17 are both not hydrogen, R14, R15, R16 and R17 are each independently only cyano, halogen, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl or (C1-C4)cyanoalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q15:
where
R4 is hydrogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkenyloxy-(C1-C4)alkyl, (C2-C4)haloalkenyloxy-(C1-C4)alkyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl or (C3-C6)cycloalkyl and
R5, R6 are independently hydrogen, cyano, halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, (C1-C4)haloalkyl-(C3-C6)cycloalkyl, cyano-(C3-C6)cycloalkyl, halo-(C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkoxyimino, (C1-C4)haloalkoxyimino, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)alkylsulfonyloxy, (C1-C4)haloalkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl or di(C1-C4)alkylaminosulfonyl
and
n is 0, 1 or 2.

### Claim 3 (depends on 2)

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(R10),
Ab is nitrogen or C(R11),
Ac is nitrogen or C(R12), and
Ad is nitrogen or C(R13),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17),
R1 is (C1-C4)alkyl, (C1-C4)hydroxyalkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C3-C6)cycloalkyl, (C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)alkylsulfinyl-(C1-C4)alkyl or (C1-C4)alkylsulfonyl-(C1-C4)alkyl,
R10, R11, R12, R13, R14, R15, R16, R17 are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, tri(C1-C4)alkylsilyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C2-C4)cyanoalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)cyanoalkoxy, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkyl sulfonyl, (C1-C4)alkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C3-C6)cycloalkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl, di(C1-C4)alkylaminosulfonyl, (C1-C4)alkylcarbamoyl (including —NHCOO(C1-C4)alkyl and —N(C1-C4)alkylCOO(C1-C4)alkyl), (C1-C4)alkylcarbonylamino, (C1-C4)alkylurea (including —NHCONH(C1-C4)alkyl and —NHCON(C1-C4)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, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)cyanoalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C2-C4)cyanoalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)alkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl, di(C1-C4)alkylaminosulfonyl, (C1-C4)alkylcarbonylamino,
where only one or two of the R10, R11, R12, R13, R14, R15, R16, R17 radicals are a substituent other than hydrogen,
and, if any of R10 and R14, R11 and R15, R12 and R16 or R13 and R17 are both not hydrogen, R14, R15, R16 and R17 are each independently only cyano, halogen, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkyl, (C1-C4)haloalkyl or (C1-C4)cyanoalkyl,
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q15,
where
R4 is hydrogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyl or (C2-C4)haloalkynyl and
R5, R6 are independently hydrogen, cyano, halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, (C1-C4)haloalkyl-(C3-C6)cycloalkyl, cyano-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkoxyimino, (C1-C4)haloalkoxyimino, (C1-C4)alkylthio, (C1-C4)haloalkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)alkylsulfonyloxy, (C1-C4)haloalkylsulfonyloxy, (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, (C1-C4)alkylsulfonylamino, (C1-C4)alkylamino, di(C1-C4)alkylamino, aminosulfonyl, (C1-C4)alkylaminosulfonyl or di(C1-C4)alkylaminosulfonyl
and
n is 0, 1 or 2.

### Claim 4 (depends on 2)

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(R10),
Ab is nitrogen or C(R1),
Ac is nitrogen or C(R12), and
Ad is nitrogen or C(R13),
where not more than two of Aa, Ab, Ac and Ad are nitrogen,
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R1)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17),
R1 is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R10, R11, R12, R13, R14, R15, R16, R17 are independently hydrogen, cyano, halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkyl sulfonyl, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, (C3-C6)cycloalkylaminocarbonyl, (C1-C4)alkylcarbamoyl (including —NHCOO(C1-C4)alkyl and —N(C1-C4)alkylCOO(C1-C4)alkyl), (C1-C4)alkylcarbonylamino or (C1-C4)alkylurea (including —NHCONH(C1-C4)alkyl and —NHCON(C1-C4)dialkyl),
where only one or two of the R10, R11, R12, R13, R14, R15, R16, R17 radicals are a substituent other than hydrogen,
and, if any of R10 and R14, R11 and R15, R12 and R16 or R13 and R17 are both not hydrogen, R14, R15, R16 and R17 are each independently only cyano, halogen, (C1-C4)alkyl or (C1-C4)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
R4 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C3-C6)cycloalkyl or (C1-C4)alkoxy-(C1-C4)alkyl,
R5 is cyano, halogen, (C1-C4)haloalkyl, halo-(C3-C6)cycloalkyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)haloalkylcarbonyl or (C1-C4)haloalkylsulfonyloxy,
R6 is hydrogen, cyano, halogen, (C1-C4)alkyl, (C1-C4)haloalkyl or (C3-C6)cycloalkyl and
n is 0, 1 or 2.

### Claim 5 (depends on 2)

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(R10),
Ab is C(R11),
Ac is C(R12) and
Ad is C(R13),
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R11)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17),
R1 is ethyl,
R10, R11, R12, R13 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 R10, R11, R12, R13 radicals are a substituent other than hydrogen,
R14, R15, R16, R17 are independently hydrogen or (C1-C4)alkyl,
Q is a heteroaromatic 9-membered fused bicyclic ring system from the group of Q2, Q3 and Q14
where
R4 is methyl,
R5 is trifluoromethyl or pentafluoroethyl,
R6 is hydrogen and
n is 0, 1 or 2.

### Claim 6 (depends on 2)

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(R10),
Ab is nitrogen or C(R11),
Ac is C(R12) and
Ad is C(R13), where
R10 is hydrogen, chlorine or trifluoromethyl,
R11 is hydrogen, chlorine, —NHCOMe or trifluoromethyl,
R12 is hydrogen, chlorine or trifluoromethyl,
R13 is hydrogen, chlorine or trifluoromethyl,
or, if represent exclusively single bonds,
Aa is C(R10)(R14),
Ab is C(R11)(R15),
Ac is C(R12)(R16) and
Ad is C(R13)(R17), where
R10, R12, R13, R14, R16, R17 are hydrogen,
R11 is hydrogen or methyl and
R15 is hydrogen or methyl,
R1 is ethyl,
Q is a heteroaromatic 9-membered fused bicyclic ring system from the group of Q2 and Q3
where
R4 is methyl,
R5 is trifluoromethyl or pentafluoroethyl,
R6 is hydrogen and
n is 0, 1 or 2.

### Claim 7 (depends on 2)

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
R4 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C3-C6)cycloalkyl or (C1-C4)alkoxy-(C1-C4)alkyl,
R5 is cyano, halogen, (C1-C4)haloalkyl, halo-(C3-C6)cycloalkyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, (C1-C4)haloalkylcarbonyl or (C1-C4)haloalkylsulfonyloxy,
R6 is hydrogen, cyano, halogen, (C1-C4)alkyl, (C1-C4)haloalkyl or (C3-C6)cycloalkyl and and Aa, Ab, Ac, Ad, R1, R10 R11, R12, R13, R14, R15, R16, R17 and n have the definitions according to claim 2.

### Claim 8 (depends on 2)

The compound of formula (Ia) or (Ib) according to claim 2,
in which
Q is Q2, Q3 or Q14
where
R4 is methyl,
R5 is trifluoromethyl or pentafluoroethyl,
R6 is hydrogen
and Aa, Ab, Ac, Ad, R1, R10 R11, R12, R13, R14, R15, R16, R17 and n have the definitions according to claim 2.

### Claim 9 (depends on 2)

The compound of formula (Ia) or (Ib) according to claim 2,
in which
Q is Q2 or Q3
where
R4 is methyl,
R5 is trifluoromethyl or pentafluoroethyl,
R6 is hydrogen
and Aa, Ab, Ac, Ad, R1, R10 R11, R12, R13, R14, R15, R16, R17 and n have the definitions according to claim 2.

### Claim 10 (depends on 2)

The compound of formula (Ia) or (Ib) according to claim 2,
in which R1 is ethyl and Aa, Ab, Ac, Ad, R10 R11, R12, R13, R14, R15, R16, R17 Q, R4, R5, R6 and n have the definitions according to claim 2.

### Claim 11 (depends on 2)

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 R1, R10, R11, R12, R13, R14, R15, R16, R17, Q, R4, R5, R6 and n have the definitions described in claim 2.

### Claim 12

A compound selected from the group consisting of

### Claim 13 (depends on 1)

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,
R1 is C1-C6 alkyl,
Aa and Ad are CH,
Ab is C(R11),
Ac is C(R12)
and
Q is Q2
where
R4 is C1-C6 alkyl,
R6 is hydrogen and
R5 is (C1-C6)haloalkyl, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl or (C1-C6)haloalkylsulfonyl,
at least one of the radicals R11 or R12 is not hydrogen, halogen or (C1-C6)haloalkyl.

### Claim 14 (depends on 1)

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,
R1 is C1-C6 alkyl,
Aa and Ad are CH,
Ab is C(R11),
Ac is C(R12)
R11 and R12 are independently hydrogen, halogen or (C1-C6)haloalkyl
and
Q is Q2
where
R4 is C1-C6 alkyl and
R6 is hydrogen,
R5 is not (C1-C6)haloalkyl, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl or (C1-C6)haloalkylsulfonyl.

### Claim 15 (depends on 1)

The compound of formula (Ia) or (Ib) according to claim 1, wherein the compound is not a compound of formula (Y)
in which
R1 is (C1-C6)alkyl,
R4 is (C1-C6)alkyl,
R5 is (C1-C6)haloalkyl, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl or (C1-C6)haloalkylsulfonyl,
R11 and R12 are independently each hydrogen, halogen or (C1-C6) haloalkyl and
n is 0, 1 or 2.

### Claim 16 (depends on 1)

The compound of formula (Ia) according to claim 1, characterized in that represents exclusively single bonds.

### Claim 17 (depends on 1)

An agrochemical formulation comprising at least one compound of formula (Ia) or (Ib) according to claim 1 and also extenders and/or surfactants.

### Claim 18 (depends on 17)

The agrochemical formulation according to claim 17, additionally comprising a further agrochemically active ingredient.

### Claim 19 (depends on 1)

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.

### Claim 20 (depends on 17)

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.