Novel halogen-substituted compounds

Abstract

The invention relates to compounds of the general formula (I), in which the radicals A 1 , A 2 , A 3 , A 4 , Lm, Q, R 1 , T and U have the meaning given in the description and to the use of the compounds for controlling animal pests. In addition, the invention relates to processes and intermediates for the preparation of the compounds according to formula (I).

1 . A method of controlling an animal pest comprising contacting said animal pest or a habitat thereof with a compound of formula (I) 
       
         
           
           
               
               
           
         
         in which 
         R 1  is hydrogen, or one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, cyano-C 1 -C 2 -alkyl, aryl(C 1 -C 3 )-alkyl, or heteroaryl(C 1 -C 3 )-alkyl, 
         A 1  is CR 2  or nitrogen, 
         A 2  is CR 3  or nitrogen, 
         A 3  is CR 4  or nitrogen, and 
         A 4  is CR 5  or nitrogen, 
         wherein not more than three of the chemical groups A 1  to A 4  are nitrogen at the same time; 
         R 2 , R 3 , R 4  and R 5 , independently of one another, are hydrogen, halogen, CN, NO 2 , optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di-C 2 -C 6 -alkylamino, N—C 2 -C 7 -alkylaminocarbonyl, N—C 2 -C 7 -cycloalkylaminocarbonyl or C 2 -C 4 -alkoxycarbonyl; 
         provided: 
         if none of the groups A 2  and A 3  is nitrogen, then R 3  and R 4 , together with the carbon to which they are bonded, can form a 5- or 6-membered ring which comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or 
         if none of the groups A 1  and A 2  is nitrogen, then R 2  and R 3 , together with the carbon to which they are bonded, can form a 6-membered ring which comprises 0, 1 or 2 nitrogen atoms; 
         U is a group C(═W), SO or SO 2 , 
         where 
         W is oxygen or sulphur; 
         L is a bivalent chemical group which is —NHC(═W)—, —NR 6 C(═W)—, —CH 2 NHC(═W)—, —CH 2 NR 6 C(═W)—, —C(═W)NH—, —C(═W)NR 6 , —C(═W)NHCH 2 —, —C(═W)NR 6 CH 2 —, —CH═N—OCH 2 C(═W)NH—, —CH═N—OCH 2 C(═W)NR 6 —, —CH 2 NHC(═W)NH—, —CH 2 NHC(═W)NR 6 —, —NH(C═W)NH—, —NH(═W)NR 6 —, —NR 6 (C═W)NH—, —NR 6 (═W)NR 6 —, —C(═W)—, —C(═W)O—, —C(═W)OCH 2 C(═W)—, —C(═W)OCH 2 C(═W)NR 6 —, —C(═W)OCH 2 C(═W)NHC(═W)NH—, —C(═W)OCH 2 C(═W)NH—, —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —Si—, —O—, —S(O) p —, —CH 2 —S(O) p —, —SO(═N—CN)—, —S(═N—CN)—, or —C(═W)NHSO 2 —, where 
         p is 0, 1 or 2; 
         R 6  is hydrogen, or one of optionally substituted groups C 1 -C 6 -alkyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl and C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl, or C 2 -C 7 -alkoxycarbonyl; 
         m is 0 or 1; 
         Q is hydrogen or one of the optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 5 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl, C 1 -C 6 -alkylaldehyde, C 1 -C 6 -hydroxyalkyl, C 2 -C 7 -alkoxycarbonyl, or C 1 -C 6 -haloalkyl; or is formyl, hydroxy, halogen, cyano, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, OR 7 , or NR 6 R 8 ; 
         R 7  is one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 8  is hydrogen or one of optionally R 9 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 9  is hydrogen or one of groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, all of which are optionally substituted by R 10 ; 
         R 10  is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, —CN, or —NO 2 ; 
         T is an optionally Z-polysubstituted saturated or unsaturated 5- or 6-membered ring, or is an optionally Z-polysubstituted 5- or 6-membered heterocyclic ring; 
         Z is hydrogen, halogen, cyano, or nitro, or is one of optionally substituted groups C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, N,N-di(C 1 -C 6 )alkylamino, —CN, —NO 2 , —C(═W)NR 11 R 5 , —C(═W)OR 12 , —S(O) 2 NR 13 R 14 , —S(O) p R 15 , or —S(O)(═NR 16 )R 17 ; or is optionally R 18 -substituted phenyl and or optionally R 18  substituted pyridinyl; 
         R 11  is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 2 -C 7 -alkylcarbonyl or C 2 -C 7 -alkoxycarbonyl; 
         R 12  is hydrogen or one of optionally R 6 -substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 13  is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl or C 2 -C 7 -alkoxycarbonyl; 
         R 14  is hydrogen or one of optionally R 19 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 15  is one of optionally R 20 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, C 1 -C 4 -haloalkyl; 
         R 16  is selected hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl or C 2 -C 7 -alkoxycarbonyl; 
         R 17  is hydrogen or is one of optionally R 20 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 18  is halogen, —OH, —NH 2 , —COOH, —CN, —NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl or N,N-di(C 1 -C 6 )-alkylaminocarbonyl; 
         R 19  is hydrogen or one of optionally R 21 -substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkyl sulphinyl, C 1 -C 6 -alkylsulphonyl, —CN, or —NO 2 ; or is optionally R 20 -substituted phenyl or is optionally R 20 -substituted pyridyl; 
         R 20  is halogen, —CN, —NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 2 -C 7 -alkylcarbonyl, C 2 -C 7 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl, or optionally R 22 -substituted phenyl or optionally R 22 -substituted pyridyl; 
         R 21  is halogen, —OH, —NH 2 , —COOH, —CN, or —NO 2  or one of optionally substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 4 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl, or N,N-di(C 1 -C 6 )-alkylaminocarbonyl; 
         R 22  is halogen, —OH, —NH 2 , —COOH, —CN, —NO 2 , —CH═N—O—CH 3 , —C(CH 3 )—N—O—CH 3 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 3 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 4 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl, or N,N-di(C 1 -C 6 )-alkylaminocarbonyl; or 
         L, Q and R 4 , together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom. 
       
     
     
         2 . The method according to  claim 1  wherein
 R 1  is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, cyano-C 1 -C 2 -alkyl, aryl(C 1 -C 3 )-alkyl, or heteroaryl(C 1 -C 3 )-alkyl; 
 A 1  is CR 2  or nitrogen, 
 A 2  is CR 3  or nitrogen, 
 A 3  is CR 4  or nitrogen, and 
 A 4  is CR 5  or nitrogen, 
 wherein at most three of the chemical groups A 1  to A 4  are nitrogen at the same time, and wherein 
 R 2 , R 3 , R 4  and R 5 , independently of one another, are hydrogen, halogen, CN, NO 2 , optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 2 -C 6 )-alkylamino, N—C 2 -C 7 -alkylaminocarbonyl, N—C 2 -C 7 -cycloalkylaminocarbonyl or C 2 -C 4 -alkoxycarbonyl, 
 provided: 
 if none of the groups A 2  and A 3  is nitrogen, then R 3  and R 4 , together with the carbon to which they are bonded, can form a 5- or 6-membered ring which comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or 
 if none of the groups A 1  and A 2  is nitrogen, then R 2  and R 3 , together with the carbon to which they are bonded, can form a 6-membered ring which comprises 0, 1 or 2 nitrogen atoms; 
 U is a group C(═W), SO or SO 2 ; 
 W is oxygen or sulphur; 
 L is a bivalent chemical group which is —NHC(═W)—, —NR 6 C(═W)—, —CH 2 NHC(═W)—, —CH 2 NR 6 C(═W)—, —C(═W)NH—, —C(═W)NR 6 —, —C(═W)NHCH 2 —, —C(═W)NR 6 CH 2 —, —CH 2 NHC(═W)NH—, —CH 2 NHC(═W)NR 6 —, —NH(C═W)NH—, —NH(═W)NR 6 —, —NR 6 (C═W)NH—, —NR 6 (═W)NR 6 —, —C(═W)—, —C(═W)O—, —C(═W)OCH 2 C(═W)—, —C(═W)OCH 2 C(═W)NR 6 —, —C(═W)OCH 2 C(═W)NHC(═W)NH—, —C(═W)OCH 2 C(═W)NH—, —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —Si—, —O—, —S(O) p —, —CH 2 —S(O) p —, —SO(═N—CN)—, —S(═N—CN)—, or —C(═W)NHSO 2 —; 
 p is 0, 1 or 2; 
 R 6  is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl, or C 2 -C 7 -alkoxycarbonyl; 
 m is 0 or 1; 
 Q is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 5 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl, C 1 -C 6 -alkylaldehyd, C 1 -C 6 -hydroxyalkyl, C 2 -C 7 -alkoxycarbonyl, C 1 -C 6 -haloalkyl, is formyl, hydroxy, halogen, cyano, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, OR 7  or NR 6 R 8 ; 
 R 7  is one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
 R 8  is hydrogen or one of optionally R 9 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
 R 9  is hydrogen or one of optionally R 10 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
 R 10  is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, —CN, or —NO 2 ; 
 T is a radical (T-1) to (T-90) which may be optionally Z-polysubstituted: 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where 
         G is oxygen, sulphur or Z-substituted nitrogen, 
         n is 0, 1, 2, 3 or 4; 
         Z is hydrogen, halogen, cyano, nitro or one of optionally substituted groups C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -Cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, N,N-di(C 1 -C 6 )-alkylamino, —CN, —NO 2 , —S(O) 2 NR 13 R 14 , —S(O) p R 15 , or —S(O)(═NR 16 )R 17  or is optionally R 18 -substituted phenyl or optionally R 18 -substituted pyridinyl; 
         R 13  is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl or C 2 -C 7 -alkoxycarbonyl; 
         R 14  is hydrogen or one of optionally R 19 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 15  is one of optionally R 20 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -Cycloalkyl, C 4 -C 7 -alkylcycloalkyl C 4 -C 7 -cycloalkylalkyl, or C 1 -C 4 -haloalkyl; 
         R 16  is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl or C 2 -C 7 -alkoxycarbonyl; 
         R 17  is hydrogen, or one of optionally R 20 -substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
         R 18  is halogen, —OH, —NH 2 , —COOH, —CN, —NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl or N,N-di(C 1 -C 6 )-alkylaminocarbonyl; 
         R 19  is hydrogen, or one of optionally R 21 -substituted groups C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkyl sulphinyl, C 1 -C 6 -alkyl sulphonyl, —CN, —NO 2 , optionally R 19 -substituted phenyl or optionally R 19 -substituted pyridyl; 
         R 20  is halogen, —CN, —NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 2 -C 7 -alkylcarbonyl, C 2 -C 7 -alkoxycarbonyl, or C 2 -C 7 -alkylaminocarbonyl; or is optionally R 22 -substituted phenyl or optionally R 22 -substituted pyridyl; 
         R 21  is halogen, —OH, —NH 2 , —COOH, —CN, —NO 2 ; or R 1  is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 4 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl, or N,N-di(C 1 -C 6 )-alkylaminocarbonyl, all of which are optionally substituted; 
         R 22  is halogen, —OH, —NH 2 , —COOH, —CN—NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkyl sulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, N,N-di(C 1 -C 6 )-alkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 4 -alkoxycarbonyl, C 2 -C 7 -alkylaminocarbonyl, or N,N-di(C 1 -C 6 )-alkylaminocarbonyl; 
         or 
         L, Q and R 4 , together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom. 
       
     
     
         3 . The method according to  claim 2  wherein
 R 1  is hydrogen or one of the optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkylene, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, cyano-C 1 -C 2 -alkyl, aryl(C 1 -C 3 )-alkyl, or heteroaryl(C 1 -C 3 )-alkyl; 
 A 1  is CR 2  or nitrogen, 
 A 2  is CR 3  or nitrogen, 
 A 3  is CR 4  or nitrogen and 
 A 4  is CR 5  or nitrogen, wherein at most three of the chemical groups A 1  to A 4  are nitrogen at the same time, and wherein 
 R 2 , R 3 , R 4  and R 5 , independently of one another, are hydrogen, halogen, CN, NO 2 , optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, N—C 2 -C 7 -alkylaminocarbonyl, or N—C 2 -C 7 -cycloalkylaminocarbonyl, 
 provided: 
 if none of the groups A 2  and A 3  is nitrogen, then R 3  and R 4 , together with the carbon to which they are bonded attached, can form a 5- or 6-membered ring which comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or 
 if none of the groups A 1  and A 2  is nitrogen, then R 2  and R 3 , together with the carbon to which they are bonded, can form a 6-membered ring which comprises 0, 1 or 2 nitrogen atoms; 
 U is a group C(═W), SO or SO 2 ; 
 W is oxygen or sulphur; 
 L is a bivalent chemical group which is —CH 2 NHC(═W)—, —CH 2 NR 6 C(═W)—, —C(═W)NH, —C(═W)NR 6 —, —NH(C═W)NH—, —NH(C═W)NR 6 —, —NR 6 (C═W)NH—, —NR 6 (═W)NR 6 —, —C(═W)—, —C(═W)O—, —C(═W)OCH 2 C(═W)—, —C(═W)OCH 2 C(═W)NR 6 —, —C(═W)OCH 2 C(═W)NHC(═W)NH—, —C(═W)OCH 2 C(═W)NH—, —O—, —S(O) p —, and —CH 2 —S(O) p —, —SO(═N—CN)—, —S(═N—CN)—, or —C(═W)NHSO 2 , 
 p is 0, 1 or 2 and 
 R 6  is hydrogen, C 1 -C 6 -alkyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, C 2 -C 7 -alkylcarbonyl, or C 2 -C 7 -alkoxycarbonyl; 
 m is 0 or 1; 
 Q is hydrogen or one of optionally substituted groups C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 5 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 7 -alkylcarbonyl, C 1 -C 6 -alkylaldehyde, C 1 -C 6 -hydroxyalkyl, C 2 -C 7 -alkoxycarbonyl, C 1 -C 6 -haloalkyl, cyano, aryl(C 1 -C 3 )-alkyl, or heteroaryl(C 1 -C 3 )-alkyl, or is a group NR 6 R 8 , where 
 R 8  is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl; 
 T is one of optionally Z-mono- or -polysubstituted heterocycles (T-5), (T-7), (T-9), (T-10), (T-12), (T-13), (T-15), (T-16), (T-19), (T-20), (T-23), (T-26), (T-28), (T-29), (T-34), (T-35), (T-36), (T-30), (T-33), (T-37), (T-46), (T-51), (T-52), or (T-53), where 
 n is 0, 1, 2, 3 or 4 and 
 Z is hydrogen, chlorine, bromine, iodine, cyano, nitro or one of optionally substituted groups C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -Cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, 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, or N,N-di(C 1 -C 4 )-alkylamino, or is optionally R 18 -substituted phenyl or optionally R 18 -substituted pyridinyl; 
 R 18  is halogen, —OH, —NH 2 , —COOH, —CN, —NO 2 , 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 -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 -alkylamino, N,N-di(C 1 -C 4 )-alkylamino, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl or N,N-di(C 1 -C 4 )-alkylaminocarbonyl; 
 or 
 L, Q and R 4 , together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom. 
 
     
     
         4 . The method according to  claim 3  wherein
 R 1  is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butynyl, isobutyl, sec-butyl, tert-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, allyl, propargyl, isopropylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, cyanomethyl, or 2-cyanoethyl; 
 A 1  is CR 2  or nitrogen, 
 A 2  is CR 3  or nitrogen, 
 A 3  is CR 4  or nitrogen and 
 A 4  is CR 5  or nitrogen, wherein at most three of the chemical groups A 1  to A 4  are nitrogen at the same time, and where 
 R 2  and R 5 , independently of one another, are hydrogen, methyl, fluorine and chlorine and 
 R 3  and R 4 , independently of one another, are hydrogen, fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl or N-cyclopropylaminocarbonyl; 
 U is C(═W), 
 W is oxygen, 
 L is a bivalent chemical group which is —C(═O)NH, —C(═O)NR 6 , —C(═O)O—, —C(═O)OCH 2 C(═O)—, —C(═O)OCH 2 C(═O)NR 6 —, —C(═O)OCH 2 C(═O)NHC(═O)NH—, —C(═O)OCH 2 C(═O)NH—, or —C(═W)NHSO 2 —, where 
 R 6  is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, cyanomethyl, or 2-cyanoethyl; 
 m is 1; 
 Q is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, bis(cyclopropyl)methyl, 2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-ynyl, 1,1-dimethylbut-2-ynyl, 3-chloroprop-2-enyl, 3,3-dichloroprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl, oxetan-3-yl, isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluoromethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl, 5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl, methoxy, 2-ethoxyethyl, 2-(methylsulphanyl)ethyl, 1-methyl-2-(ethylsulphanyl)ethyl, 2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH 2 , N-ethylamino, N-allylamino, N,N-dimethylamino, or N,N-diethylamino; 
 T is one of optionally Z-polysubstituted heterocycles (T-12), (T-13), (T-15), (T-16), (T-19), (T-20), (T-23), (T-26), (T-30), (T-33), (T-37), (T-46), (T-51), (T-52), or (T-53); 
 n is 0, 1, 2 or 3 and 
 Z is hydrogen, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, ethynyl, 1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, chloromethyl, bromomethyl, 1-fluoro ethyl, 1-fluoro-1-methylethyl, 2-fluoro ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, trifluoromethoxy-1,1,2,2-tetrafluoroethoxydifluoromethyl, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methoxy, ethoxy, n-propoxy, trifluoromethoxy, difluoromethoxy, cyclopropyl, cyclobutyl, 2,2,2-trifluoroethoxy, 1-trifluoromethylethoxy, 3,3,3,2,2-pentafluoropropoxy, 4-fluorophenyl, 4-chlorphenyl, 4-trifluoromethylphenyl, 2,2,2-trifluoroethyl, 2,2-difluoro-1-methylcyclopropyl, phenyl, methoxymethyl, cyclopropyl(fluoro)methyl, 2,4-dichlorophenyl, 4-trifluoromethoxyphenyl, 2-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, or (1,1,1,3,3-hexafluoropropan-2-yl)oxy; 
 or 
 L, Q and R 4 , together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom. 
 
     
     
         5 . The method according to  claim 2  wherein the compound of formula (I) is a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Ik), (Il), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu) or (Iv): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where the groups and substituents A 1 , A 2 , A 3 , A 4 , U and R 1  are defined in  claim 2 , and Z 1 , Z 2  and Z 3 , in each case independently, are defined in  claim 2 . 
       
     
     
         6 - 14 . (canceled) 
     
     
         15 . The method according to  claim 1  wherein said animal pest is an insect, arachnid, or nematode. 
     
     
         16 . A medicament comprising a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 . 
     
     
         17 . A pharmaceutical composition comprising a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 . 
     
     
         18 . A crop protection composition comprising a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 , and extenders and/or surface-active substances. 
     
     
         19 . A method of controlling a pest comprising allowing a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 , to act on said pest or a habitat thereof. 
     
     
         20 . A method of protecting propagation material of plants comprising contacting a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 , with said propagation material. 
     
     
         21 . The method according to  claim 20  wherein said propagation material is seed material. 
     
     
         22 . A process of preparing a crop protection composition comprising mixing the compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 , with extenders and/or surface-active substances. 
     
     
         23 . A process of preparing a pharmaceutical composition comprising mixing the compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to  claim 5 , with a pharmaceutically acceptable excipient and/or auxiliary.