2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
The invention relates to novel compounds of the formula (I) in welcher R 1 , R 2 , R 3 , A 1 , X and n have the meanings given above, to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.
1. A compound of formula (I)
wherein
A 1 represents nitrogen or ═C—R 4 ,
R 1 represents (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 represents a 5- or 6-membered saturated, partially saturated or heteroaromatic ring from the group consisting of Q1 to Q101 which is optionally mono- or disubstituted by identical or different substituents, which may in each case contain at least one carbonyl group and/or where possible substituents are in each case as follows: hydrogen, cyano, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, halogen, amino, (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(H)═N—O(C 1 -C 4 )alkyl, (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 )alkylsulphonyl-(C 1 -C 4 )alkyl, (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, (C 1 -C 4 )alkylcarbonylamino,
where the bond to the remainder of the molecule is identified by an asterisk *,
R 3 represents hydrogen, cyano, halogen, nitro, hydroxy, 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, NHCO—(C 1 -C 4 )alkyl ((C 1 -C 4 )alkylcarbonylamino), or
represents phenyl or hetaryl, each of which is optionally mono- or disubstituted by identical or different substituents, where (in the case of hetaryl) at least one carbonyl group may optionally be present and/or 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, halogen(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 )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, NHCO—(C 1 -C 4 )alkyl ((C 1 -C 4 )alkylcarbonylamino),
R 4 represents hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl,
X represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series H1 to H20,
where the bond to the remainder of the molecule is identified by a diamond # ,
R 5 , R 6 independently of one another represent 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,
R 7 represents (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,
n represents 0, 1 or 2,
where if R 2 represents optionally substituted Q45, then X is not H1, H2 or H4.
2. The compound of formula (I) according to claim 1 wherein
A 1 represents nitrogen or ═C—R 4 ,
R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 2 represents a ring optionally monosubstituted by cyano, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulphonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylcarbonylamino, selected from Q-25, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-52 or Q-95
R 3 represents hydrogen, cyano, halogen, (C 1 -C 4 )alkyl, (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 4 represents hydrogen, fluorine, chlorine, bromine or cyano,
X represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series H1, H2, H3, H4, H5, H7, H8, H10, H11, H12, H13, H15, H16, H17, H18, H19, or H20,
R 5 represents 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 )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 represents hydrogen,
R 7 represents (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy-(C 1 -C 4 )-alkyl,
n represents 0, 1 or 2,
where if R 2 represents optionally substituted Q45, then X is not H1, H2 or H4.
3. The compound of formula (I) according to claim 1 wherein
A 1 represents nitrogen,
R 1 represents methyl, ethyl, n-propyl, isopropyl or cyclopropyl,
R 2 represents a ring optionally monosubstituted by fluorine, chlorine, bromine, iodine, trifluoromethyl, difluoromethyl or pentafluoroethyl from the series Q-42, Q-43, Q-45 or Q-47,
R 3 represents hydrogen,
X represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series H1, H2, H5, H15, H16, H17 or H19,
R 5 represents fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl or trifluoromethylsulphinyl,
R 6 represents hydrogen,
R 7 represents methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl,
n represents 0, 1 or 2,
where if R 2 represents optionally substituted Q45, then X is not H1 or H2.
4. The compound of formula (I) according to claim 1 wherein
A 1 represents nitrogen,
R 1 represents ethyl,
R 2 represents a ring optionally monosubstituted by fluorine, chlorine, or trifluoromethyl from the series Q-42, Q-43, Q-45 or Q-47,
R 3 represents hydrogen,
X represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series H1, H2, H5, H15, H16, H17 or H19,
R 5 represents trifluoromethyl
R 6 represents hydrogen,
R 7 represents methyl,
n represents 0, 1 or 2,
where if R 2 represents optionally substituted Q45, then X is not H1 or H2.
5. The compound of formula (I) according to claim 1 wherein
R 2 represents a radical from the following series:
where if R 2 represents optionally substituted Q45, then X is not H1 or H2.
6. The compound of formula (I) according to claim 1 wherein
X represents a radical from the following series:
where if R 2 represents optionally substituted Q45, then X is not H1 or H2.
7. The compound of formula (I) according to claim 1 , where the substituents R 1 , R 2 , R 3 , A 1 , X and n have the meanings given in the table below and where the bond from X and R 2 to the remainder of the molecule is characterized by a wavy line:
Ex.
R 1
n
A 1
R 3
X
R 2
Ex. I-1
—CH 2 CH 3
2
N
H
Ex. I-4
—CH 2 CH 3
2
N
H
Ex. I-9
—CH 2 CH 3
2
N
H
Ex. I-12
—CH 2 CH 3
1
N
H
Ex. I-13
—CH 2 CH 3
2
N
H
Ex. I-14
—CH 2 CH 3
2
N
H
Ex. I-17
—CH 2 CH 3
2
N
H
Ex. I-18
—CH 2 CH 3
2
N
H
Ex. I-23
—CH 2 CH 3
2
N
H
Ex. I-24
—CH 2 CH 3
2
N
H
Ex. I-27
—CH 2 CH 3
2
N
H
Ex. I-28
—CH 2 CH 3
2
N
H
Ex. I-29
—CH 2 CH 3
2
N
H
Ex. I-30
—CH 2 CH 3
2
N
H
Ex. I-33
—CH 2 CH 3
2
N
H
Ex. I-35
—CH 2 CH 3
2
N
H
Ex. I-41
—CH 2 CH 3
2
N
H
Ex. I-42
—CH 2 CH 3
2
N
H
Ex. I-43
—CH 2 CH 3
2
N
H
Ex. I-44
—CH 2 CH 3
2
N
H
Ex. I-45
—CH 2 CH 3
2
N
H
Ex. I-46
—CH 2 CH 3
2
N
H
8. An agrochemical formulation comprising the compound of formula (I) according to claim 1 and one or more extenders and/or surfactants.
9. The agrochemical formulation according to claim 8 , additionally comprising a further agrochemically active compound.
10. A method for controlling one or more animal pests, comprising allowing the compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.
11. A product comprising the compound of formula (I) according to claim 1 or an agrochemical formulation thereof for controlling one or more animal pests.
12. A method for controlling one or more animal pests, comprising allowing the compound of formula (I) according to claim 2 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.
13. A method for controlling one or more animal pests, comprising applying the compound of formula (I) according to claim 1 or an agrochemical formulation thereof to a plant, a part of a plant, a seed of a plant, or soil.
14. A method for controlling one or more animal pests, comprising administering a medicament comprising the compound of formula (I) according to claim 1 to an animal.
15. The method according to claim 14 , wherein the animal is a mammal.
16. A method for controlling one or more animal pests, comprising administering a medicament comprising the compound of formula (I) according to claim 7 to an animal.
17. A method for controlling one or more animal pests, comprising applying the compound of formula (I) according to claim 7 or an agrochemical formulation thereof to a plant, a part of a plant, a seed of a plant, or soil.