Condensed bicyclic heterocyclic derivatives as pest control agents
The invention relates to novel compounds of formula (I), in which Aa, Ab, Ac, Ad, Ae, Q, R 1 and n are defined as in the description, to the use thereof as acaricides and/or insecticides for controlling animal pests, and to processes and intermediate products for the preparation thereof.
1. A compound of formula (I)
wherein
Aa represents nitrogen or =C(R 7 )—,
Ab represents nitrogen or =C(R 8 )—,
Ac represents nitrogen or =C(R 9 )—,
Ad represents nitrogen or =C(R 10 )—,
Ae represents nitrogen or =C(R 11 )—,
wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen,
resulting in the following structural units: A1, A2, A6, A11, or A16,
R 1 represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 3 -C 6 )-cycloalkyl,
R 7 represents hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl,
R 8 , R 10 , R 11 independently of one another represent hydrogen, (C 1 -C 4 )-alkyl or halogen,
R 9 represents cyano (C 3 -C 6 ) cycloalkyl,
wherein only one or two of the radicals R 8 , R 9 , R 10 , R 11 represent a substituent other than hydrogen,
Q is represented by Q1, Q4, Q10, Q11, Q14, Q15, Q19, Q20 or Q21,
R 4 represents (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl,
R 5 represents hydrogen, cyano, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (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 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-haloalkylsulfonyl, (C 1 -C 4 )-alkylcarbonyl or (C 1 -C 4 )-haloalkylcarbonyl,
R 6 represents hydrogen,
R 6a represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl or (C 3 -C 6 )-cycloalkyl,
and
n represents 0, 1 or 2.
2. The compound of claim 1 wherein
Aa represents ═C(R 7 )—,
Ab represents ═C(R 8 )—,
Ac represents ═C(R 9 )—,
Ad represents ═C(R 10 )—,
Ae represents ═C(R 11 )—,
R 1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R 7 represents hydrogen,
R 8 represents hydrogen,
R 9 represents cyanocyclopropyl or cyanocyclobutyl,
R 10 represents hydrogen,
R 11 represents hydrogen,
Q represents Q1, Q4, or Q21,
R 4 represents methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl,
R 5 represents 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, pentafluoroethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
R 6 represents hydrogen,
R 6a represents methyl, and
n represents 0, 1 or 2.
3. The compound of claim 1 wherein
Aa represents ═C(R 7 )—,
Ab represents ═C(R 8 )—,
Ac represents ═C(R 9 )—,
Ad represents ═C(R 10 )—,
Ae represents ═C(R 11 )—,
R 1 represents ethyl,
R 7 represents hydrogen,
R 8 represents hydrogen,
R 9 represents 1-cyanocyclopropyl,
R 10 represents hydrogen,
R 11 represents hydrogen,
Q represents Q1, Q4, or Q21,
R 4 represents methyl,
R 5 represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl,
R 6 represents hydrogen,
R 6a represents methyl, and
n represents 2.
4. The compound of claim 1 , wherein
Aa represents nitrogen or =C(R 7 )—,
Ab represents nitrogen or =C(R 8 )—,
Ac represents nitrogen or =C(R 9 )—,
Ad represents nitrogen or =C(R 10 )—,
Ae represents nitrogen or =C(R 11 )—,
wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen,
resulting in the structural unit: A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, or A17.
5. The compound of claim 1 , wherein
Aa represents nitrogen or =C(R 7 )—,
Ab represents nitrogen or =C(R 8 )—,
Ac represents nitrogen or =C(R 9 )—,
Ad represents nitrogen or =C(R 10 )—,
Ae represents nitrogen or =C(R 11 )—,
wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen,
resulting in the structural unit: A1, A2, A6, A7, A9, A11, A13, or A16.
6. The compound of claim 1 , wherein
Aa represents ═C(R 7 )—,
Ab represents ═C(R 8 )—,
Ac represents ═C(R 9 )—,
Ad represents ═C(R 10 )—,
Ae represents ═C(R 11 )—,
R 1 represents ethyl,
R 7 represents hydrogen,
R 8 represents hydrogen,
R 9 represents 1-cyanocyclopropyl
R 10 represents hydrogen,
R 11 represents hydrogen,
Q is Q1,
R 4 represents methyl,
R 5 represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl,
R 6 represents hydrogen, and
n represents 2.
7. The compound of claim 1 , wherein
Aa represents ═C(R 7 )—,
Ab represents ═C(R 8 )—,
Ac represents ═C(R 9 )—,
Ad represents ═C(R 10 )—,
Ae represents ═C(R 11 )—,
R 1 represents ethyl,
R 7 represents hydrogen,
R 8 represents hydrogen,
represents 1-cyanocyclopropyl,
R 10 represents hydrogen,
R 11 represents hydrogen,
Q is Q4,
R 4 represents methyl,
R 5 represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl,
R 6 represents hydrogen, and
n represents 2.
8. The compound of claim 1 , wherein
Aa represents ═C(R 7 )—,
Ab represents ═C(R 8 )—,
Ac represents ═C(R 9 )—,
Ad represents ═C(R 10 )—,
Ae represents ═C(R 11 )—,
R 1 represents ethyl,
R 7 represents hydrogen,
R 8 represents hydrogen,
R 9 represents 1-cyanocyclopropyl,
R 10 represents hydrogen,
R 11 represents hydrogen,
Q is Q21,
R 4 represents methyl,
R 5 represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl,
R 6 represents hydrogen,
R 6a represents methyl, and
n represents 2.
9. An agrochemical formulation comprising one or more compounds of claim 1 and one or more extenders and/or surfactants.
10. A method of controlling one or more animal pests, comprising administering a formulation of claim 9 on or around a plant and allowing the agrochemical formulation of claim 7 to act on the animal pests and/or a habitat thereof.
11. The agrochemical formulation as claimed in claim 9 , additionally comprising a further agrochemically active compound.
12. A method of controlling one or more animal pests, comprising administering a compound of claim 3 on or around a plant and allowing a compound of claim 3 to act on the animal pests and/or a habitat thereof.
13. The method of claim 12 wherein the administering comprises dipping, spraying, evaporating, fogging, scattering, painting on, injecting, or a combination thereof.
14. The method of claim 4 wherein the administering comprises dipping, spraying, evaporating, fogging, scattering, painting on, injecting, or a combination thereof.