Active compound combinations having insecticidal properties

Abstract

The invention relates to novel insecticidal active compound combinations comprising, firstly, anthrlamides (group 1) and, secondly, further insecticidal active compounds selected from the group of the (thio)phosphates (group 2) and/or the group of the carbamates (group 3), which combinations are highly suitable for controlling animal pests, such as insects.

1 . A composition comprising a synergistically effective combination of compounds of the formula (I)  
     
       
         
         
             
             
         
       
     
     in which 
 A 1  and A 2  independently of one another represent oxygen or sulfur,  
 X 1  represents N or CR 10 ,  
 R 1  represents hydrogen or represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R 6 , halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 2 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkylamino and R 11 ,  
 R 2  represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -alkylcarbonyl,  
 R 3  represents hydrogen, R 11  or represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R 6 , halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -trialkylsilyl, R 11 , phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R 12 , or  
 R 2  and R 3  may be attached to one another and form the ring M,  
 R 4  represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino, C 3 -C 6 -trialkylsilyl or represents phenyl, benzyl or phenoxy, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino, C 3 -C 6 -(alkyl)cycloalkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl and C 3 -C 6 -trialkylsilyl,  
 R 5  and R 8  in each case independently of one another represent hydrogen, halogen or represent in each case optionally substituted C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, R 12 , G, J, —OJ, —OG, —S(O) p -J, —S(O) p -G, —S(O) p -phenyl, where the substituents independently of one another may be selected from one to three radicals W or from the group consisting of R 12 , C 1 -C 10 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkylthio, where each substituent may be substituted by one or more substituents independently of one another selected from the group consisting of G, J, R 6 , halogen, cyano, nitro, amino, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -trialkylsilyl, phenyl and phenoxy, where each phenyl or phenoxy ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R 12 ,  
 G in each case independently of one another represent a 5- or 6-membered non-aromatic carbocyclic or heterocyclic ring which may optionally contain one or two ring members from the group consisting of C(═O), SO and S(═O) 2  and which may optionally be substituted by one to four substituents independently of one another selected from the group consisting of C 1 -C 2 -alkyl, halogen, cyano, nitro and C 1 -C 2 -alkoxy, or independently of one another represent C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, (cyano)-C 3 -C 7 -cycloalkyl, (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, where each cycloalkyl, (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be substituted by one or more halogen atoms,  
 J in each case independently of one another represent an optionally substituted 5- or 6-membered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R 12 ,  
 R 6  independently of one another represent —C(=E 1 )R 19 , -LC(=E 1 )R 19 , —C(=E 1 )LR 19 , -LC(=E 1 )LR 19 , —OP(=Q)(OR 19 ) 2 , —SO 2 LR 18  or -LSO 2 LR 19 , where each E 1  independently of one another represents O, S, N—R 15 , N—OR 15 , N—N(R 15 ) 2 , N—S═O, N—CN or N—NO 2 ,  
 R 7  represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -halo-alkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl,  
 R 9  represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylsulfinyl or halogen,  
 R 10  represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen, cyano or C 1 -C 4 -haloalkoxy,  
 R 11  in each case independently of one another represents in each case optionally mono- to trisubstituted C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfenyl, C 1 -C 6 -haloalkythio, C 1 -C 6 -haloalkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list W, —S(O) n N(R 16 ) 2 , —C(═O)R 13 , -L(C═O)R 14 , —S(C═O)LR 14 , —C(═O)LR 13 , —S(O) n NR 13 C(=O)R 13 , —S(O) n NR 13 C(═O)LR 14  or —S(O) n NR 13 S(O) 2 LR 14 ,  
 L in each case independently of one another represents O, NR 18  or S,  
 R 12  in each case independently of one another represents —B(OR 17 ) 2 , amino, SH, thiocyanato, C 3 -C 8 -trialkylsilyloxy, C 1 -C 4 -alkyl disulfide, —SF 5 , —C(=E 1 )R 19 , -LC(=E 1 )R 19 , —C(=E 1 )LR 19 , -LC(=E 1 )LR 19 , —OP(=Q)(OR 19 ) 2 , —SO 2 LR 19  or -LSO 2 LR 19 ,  
 Q represents O or S,  
 R 13  in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R 6 , halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino or (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkylamino,  
 R 14  in each case independently of one another represent in each case optionally mono- or polysubstituted C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl or C 3 -C 6 -cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R 6 , halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino and (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkylamino or represent optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R 12 ,  
 R 15  in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C 1 -C 6 -haloalkyl or C 1 -C 6 -alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R 12 , or N(R 5 ) 2  represents a cycle which forms the ring M,  
 R 16  represents C 1 -C 12 -alkyl or C 1 -C 12 -haloalkyl, or N(R 16 ) 2  represents a cycle which forms the ring M,  
 R 17  in each case independently of one another represent hydrogen or C 1 -C 4 -alkyl, or B(OR 17 ) 2  represents a ring in which the two oxygen atoms are attached via a chain having two to three carbon atoms which are optionally substituted by one or two substituents independently of one another selected from the group consisting of methyl and C 2 -C 6 -alkoxycarbonyl,  
 R 18  in each case independently of one another represent hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, or N(R 13 )(R 8 ) represents a cycle which forms the ring M,  
 R 19  in each case independently of one another represent hydrogen or represent in each case mono- or polysubstituted C 1 -C 6 -alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, CO 2 H, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl or phenyl or pyridyl, each of which is optionally mono- to trisubstituted by W,  
 M in each case represents an optionally mono- to tetrasubstituted ring which, in addition to the nitrogen atom attached to the substituent pair R 13  and R 18 , (R 15 ) 2  or (R 16 ) 2 , contains two to six carbon atoms and optionally additionally a further nitrogen, sulfur or oxygen atom, where the substituents independently of one another may be selected from the group consisting of C 1 -C 2 -alkyl, halogen, cyano, nitro and C 1 -C 2 -alkoxy,  
 W in each case independently of one another represent C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkylamino, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, CO 2 H, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl or C 3 -C 6 -trialkylsilyl,  
 n in each case independently of one another represent 0 or 1,  
 p in each case independently of one another represent 0, 1 or 2,  
 where, if (a) R 5  represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio or halogen and (b) R 8  represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, halogen, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl or C 3 -C 8  dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R 6 , R 11  and R 12  is present and (d) if R 12  is not present, at least one of the radicals R 6  and R 11  is different from C 2 -C 6 -alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl and C 3 -C 8 -dialkylaminocarbonyl, and where the compound of the general formula (I) may also be an N-oxide or salt,  
 and at least one insecticidally active compound of groups 2 and 3 below selected from  
 A) (group 2), 
 (2-1) azinphos-methyl  
                     
 and/or  
 (2-2) chlorpyrifos  
                     
 and/or  
 (2-3) diazinon  
                     
 and/or  
 (2-4) dimethoate  
                     
 and/or  
 (2-5) disulfoton  
                     
 and/or  
 (2-6) ethion  
                     
 and/or  
 (2-7) fenitrothion  
                     
 and/or  
 (2-8) fenthion  
                     
 and/or  
 (2-9) isoxathion  
                     
 and/or  
 (2-10) malathion  
                     
 and/or  
 (2-11) methidathion  
                     
 and/or  
 (2-12) oxydemeton-methyl  
                     
 and/or  
 (2-13) parathion  
                     
 and/or  
 (2-14) parathion-methyl  
                     
 and/or  
 (2-15) phenthoate  
                     
 and/or  
 (2-16) phorate  
                     
 and/or  
 (2-17) phosalone  
                     
 and/or  
 (2-18) phosmet  
                     
 and/or  
 (2-19) phoxim  
                     
 and/or  
 (2-20) pirimiphos-methyl  
                     
 and/or  
 (2-21) profenophos  
                     
 and/or  
 (2-22) prothiophos  
                     
 and/or  
 (2-23) tebupirimphos  
                     
 and/or  
 (2-24) triazophos  
                     
 and/or  
 (2-25) chlorfenvinphos  
                     
 and/or  
 (2-26) dichlorphos  
                     
 and/or  
 (2-27) dicrotophos  
                     
 and/or  
 (2-28) mevinphos  
                     
 and/or  
 (2-29) monocrotophos  
                     
 and/or  
 (2-30) phosphamidon  
                     
 and/or  
 (2-31)  
                     
 and/or  
 (2-32) methamidophos  
                     
 and/or  
 (2-33) trichlorfon  
                     
 and/or  
 
 B) (group 3), 
 (3-1) carbaryl  
                     
 and/or  
 (3-2) fenoxycarb  
                     
 and/or  
 (3-3) formetanate  
                     
 and/or  
 (3-4) formetanate hydrochloride  
 and/or  
 (3-5) methiocarb  
                     
 and/or  
 (3-6) methomyl  
                     
 and/or  
 (3-7) oxamyl  
                     
 and/or  
 (3-8) pirimicarb  
                     
 and/or  
 (3-9) propoxur  
                     
 and/or  
 (3-10) thiodicarb  
                     
 
 
   
   
       2 . The composition as claimed in  claim 1  comprising at least one compound of the formula (I-1) in which:  
     
       
         
         
             
             
         
       
     
     in which 
 R 2  represents hydrogen or C 1 -C 6 -alkyl,  
 R 3  represents C 1 -C 6 -alkyl which is optionally substituted by one R 6 ,  
 R 4  represents C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or halogen,  
 R 5  represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or halogen,  
 R 6  represents —C(=E 2 )R 19 , -LC(=E 2 )R 19 , —C(=E 2 )LR 19  or -LC(=E 2 )LR 19 , where each E 2  independently of one another represents O, S, N—R 15 , N—OR 15 , N—N(R 5 ) 2 , and each L independently of one another represents O or NR 18 ,  
 R 7  represents C 1 -C 4 -haloalkyl or halogen,  
 R 9  represents C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, S(O) p —C 1 -C 2 -haloalkyl or halogen,  
 R 15  in each case independently of one another represent hydrogen or represent in each case optionally substituted C 1 -C 6 -haloalkyl or C 1 -C 6 -alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl and C 1 -C 4 -haloalkylsulfonyl,  
 R 18  in each case represents hydrogen or C 1 -C 4 -alkyl,  
 R 19  in each case independently of one another represent hydrogen or C 1 -C 6 -alkyl,  
 and  
 p independently of one another represent 0, 1, 2.  
 
   
   
       3 . The composition as claimed in  claim 1  or  2  comprising at least one compound selected from the group consisting of 
 (2-2) chlorpyrifos,    (2-31) acephate,    (2-32) methamidophos,    (3-1) carbaryl,    (3-5) methiocarb, and    (3-10) thiodicarb.    
   
   
       4 . The composition as claimed in  claim 1 , comprising at least one compound of formula (I) and at least one compound from group 2 and/or group 3 in a ratio of 50:1 to 1:50.  
   
   
       5 . (canceled)  
   
   
       6 . A process for preparing pesticides, comprising contacting a synergistically effective mixture as defined in  claim 1 , with extenders and/or surfactants.  
   
   
       7 . A method for controlling animal pests, comprising allowing a synergistically effective mixture as defined in  claim 1 , to act on animal pests and/or their habitat.