Nitrogen-containing heterocycles as pesticides
The present application relates to novel heterocyclic compounds, to processes and intermediates for the preparation thereof, and their use for controlling animal pests.
1. A compound of formula (I)
wherein the structural unit of the formula
represents a radical A selected from the group consisting of
wherein these radicals carry m substituents X,
X represents a radical selected from the group consisting of halogen, cyano (CN), nitro, alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphonyl, alkoxycarbonyl, alkylcarbonyl and cycloalkylcarbonyl,
m represents a number selected from the group consisting of 0, 1 and 2,
R represents a radical B selected from the group consisting of
wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A,
Y represents a radical selected from the group consisting of halogen, cyano, nitro, amino, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkoxycarbonyl, alkylcarbonyl, cycloalkylcarbonyl, alkylamino, dialkylamino, alkylaminosulphonyl, dialkylaminosulphonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxyalkylcarbonylamino, haloalkylcarbonylamino and in each case optionally substituted aryl and hetaryl,
n represents a number selected from the group consisting of 0, 1 and 2,
W represents CH or N (nitrogen) and
R 1 represents a radical selected from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 .
2. The compound of formula (I) according to claim 1
wherein the structural unit of the formula
represents a radical A selected from the group consisting of
wherein these radicals carry m substituents X,
X represents a radical selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl and C 3 -C 6 -cycloalkylcarbonyl,
m represents a number selected from the group consisting of 0, 1 and 2,
R represents a radical B selected from the group consisting of
wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A,
Y represents a radical selected from the group consisting of halogen, cyano, nitro, amino, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halo-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylaminosulphonyl, di-(C 1 -C 4 -alkyl)aminosulphonyl, C 1 -C 4 -alkylaminocarbonyl, di-(C 1 -C 4 -alkyl)aminocarbonyl, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkylcarbonylamino, halo-C 1 -C 4 -alkylcarbonylamino, in each case optionally substituted aryl and 5- or 6-membered hetaryl and in the case of aryl and hetaryl in particular in each case optionally halogen-, cyano-, C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, halo-C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, halo-C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, halo-C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or halo-C 1 -C 4 -alkylsulphonyl-substituted phenyl and 5- or 6-membered hetaryl, wherein hetaryl is preferably selected from the group consisting of N-pyrazolyl, N-imidazolyl and N-1,2,4-triazolyl,
n represents a number selected from the group consisting of 0, 1 and 2,
W represents CH or N (nitrogen) and
R 1 represents a radical selected from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 .
3. The compound of formula (I) according to claim 1
wherein the structural unit of the formula
represents a radical A selected from the group consisting of
wherein these radicals carry m substituents X,
X represents a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, and halo-C 1 -C 4 -alkyl,
m represents a number selected from the group consisting of 0, 1 and 2,
R represents a radical B selected from the group consisting of
wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A,
Y represents a radical selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halo-C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkylsulphonyl and 5-membered hetaryl which is optionally substituted by a substituent from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, and halo-C 1 -C 4 -alkylsulphonyl,
n represents a number selected from the group consisting of 0, 1 and 2,
W represents N (nitrogen) and
R 1 represents cyano or CO—CF 3 .
4. The compound of formula (I) according to claim 1
wherein the structural unit of the formula
represents a radical A selected from the group consisting of
wherein these radicals carry m substituents X,
X represents a radical selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl and difluoromethyl,
m represents a number selected from the group consisting of 0, 1 and 2,
R represents a radical selected from the group consisting of
wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A,
Y represents a radical selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, difluorobromomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, difluoromethyl, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, difluoromethylsulphinyl, trifluoromethylsulphinyl, difluoromethylsulphonyl, trifluoromethylsulphonyl, N-triazolyl and N-pyrazolyl which is optionally substituted by a substituent from the group consisting of fluorine, chlorine, iodine, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy and methylthio,
n represents a number selected from the group consisting of 0, 1 and 2,
W represents N (nitrogen) and
R 1 represents cyano.
5. A composition comprising at least one compound of the formula (I) according to claim 1 and one or more extenders and/or surfactants.
6. The compound of formula (I) according to claim 1 , wherein the compound is of formula (I-P-1),
7. The compound of formula (I-P-1) according to claim 6 , wherein
W represents N (nitrogen),
Y represents fluorine, and
R 1 represents cyano.
8. A method of controlling an animal pest comprising applying the compound of formula (I) according to claim 1 to the animal pest or habitat thereof.
9. The method according to claim 8 , wherein the animal pest is an insect, arachnid, helminth, nematode, or mollusc.
10. The method according to claim 8 , wherein the animal pest is selected from the group consisting of Boophilus microplus, Ctenocephalides felis, Lucilia cuprina, Myzus persicae, Phaedon cochleariae, Spodoptera frugiperda , and Tetranychus urticae.
11. The compound of formula (I) according to claim 1 , which is
12. The compound of formula (I) according to claim 1 , which is
13. The compound of formula (I) according to claim 1 , which is
14. The compound of formula (I) according to claim 1 , which is