Avermectins substituted in the 4"-position having pesticidal properties

Abstract

What is described are a compound of the formula in which R 1 is C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl or C 2 -C 12 alkenyl; R 2 is H, unsubstituted or mono- to pentasubstituted C 1 -C 12 alkyl or unsubstituted or mono- to pentasubstituted C 2 -C 12 alkenyl; R 3 is C 2 -C 12 alkyl, mono- to pentasubstituted C 1 -C 12 alkyl, unsubstituted or mono- to pentasubstituted C 3 -C 12 cycloalkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl; or R 2 and R 3 together are an alkylene or alkenylene bridge; with the proviso that R 1 is not sec-butyl or isopropyl if R 2 is H and R 3 is 2 -hydroxyethyl, isopropyl, n-octyl or benzyl; or, if appropriate, an E/Z isomer, an E/Z isomer mixture and/or a tautomer; a process for preparing and using these compounds and their tautomers; pesticides whose active compound is selected from these compounds and their tautomers; and a process for preparing these compounds and compositions, and the use of these compounds and compositions.

What is claimed is:  
     
         1 . A compound of the formula  
       
         
           
           
               
               
           
         
       
       in which 
 R 1  is C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl or C 2 -C 12 alkenyl;  
 R 2  is H, unsubstituted or mono- to pentasubstituted C 1 -C 12 alkyl or unsubstituted or mono- to pentasubstituted C 2 -C 12 alkenyl;  
 R 3  is C 2 -C 12 alkyl, mono- to pentasubstituted C 1 -C 12 alkyl, unsubstituted or mono- to pentasubstituted C 3 -C 12 cycloalkyl, unsubstituted or mono- to pentasubstituted C 2 -C 12 alkenyl, unsubstituted or mono- to pentasubstituted C 2 -C 12 alkynyl; or  
 R 2  and R 3  together are a three- to seven-membered alkylene or a four- to seven-membered alkenylene bridge, in which a CH 2  group may be substituted by O, S or NR 4 ; 
 in which the substituents of the alkyl, alkenyl, alkynyl, alkylene, alkenylene and cycloalkyl radicals mentioned are selected from the group consisting of OH, halogen, halo-C 1 -C 2 alkyl, CN, NO 2 , C 2 -C 6 alkynyl, C 3 -C 8 -cycloalkyl which is unsubstituted or substituted by one to three methyl groups, norbornylenyl, C 3 -C 8 -cycloalkenyl which is unsubstituted or substituted by one to three methyl groups, C 3 -C 8 halocycloalkyl, C 1 -C 12 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 3 -C 8 cycloalkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 12 -haloalkylthio, C 1 -C 12 alkylsulfinyl, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 12 haloalkylsulfinyl, C 3 -C 8 halocycloalkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 3 -C 8 halocycloalkylsulfonyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , —C(═O)R 5 , —NHC(═O)R 6 , —P(═O)(OC 1 -C 6 alkyl) 2 ;  
 aryl, heterocyclyl, aryloxy, heterocyclyloxy; and also aryl, heterocyclyl, aryloxy and heterocyclyloxy which, depending on the possibilities of substitution on the ring, are mono- to pentasubstituted by substituents selected from the group consisting of OH, halogen, CN, NO 2 , C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, dimethylamino-C 1 -C 6 alkoxy, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenoxy, phenyl-C 1 -C 6 alkyl; phenoxy which is unsubstituted or mono- to trisubstituted independently of one another by halogen, methoxy, trifluoromethyl or trifluoromethoxy; phenyl-C 1 -C 6 alkoxy which is unsubstituted or mono- to trisubstituted in the aromatic ring independently of one another by halogen, methoxy, trifluoromethyl or trifluoromethoxy; phenyl-C 2 -C 6 alkenyl, phenyl-C 2 -C 6 alkynyl, methylenedioxy, —C(═O)R 5 , —O—C(═O)R 6 , —NH—C(═O)R 6 , NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , C 1 -C 6 alkylsulfinyl, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 3 -C 8 halocycloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 haloalkylsulfonyl and C 3 -C 8 halocycloalkylsulfonyl;  
 
 R 4  is C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl or —C(═O)—R 5 ;  
 R 5  is H, OH, SH, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 12 alkylthio, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy; phenyl, phenoxy, benzyloxy, NH-phenyl, —N(C 1 -C 6 alkyl)-phenyl, NH—C 1 -C 6 alkyl-C(═O)—R 7 , —N(C 1 -C 6 alkyl)-C 1 -C 6 alkyl-C(═O)—R 7 ; or phenyl, phenoxy, benzyloxy, NH-phenyl or —N(C 1 -C 6 alkyl)-phenyl which are mono to trisubstituted in the aromatic ring independently of one another by halogen, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy;  
 R 6  is H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, benzyl, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , —NH-phenyl or —N(C 1 -C 12 alkyl)-phenyl; and  
 R 7  is H, OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 2 -C 8 alkenyloxy, phenyl, phenoxy, benzyloxy, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , —NH-phenyl or —N(C 1 -C 12 alkyl)-phenyl; 
 with the proviso that R 1  is not sec-butyl or isopropyl if R 2  is H and R 3  is 2-hydroxyethyl, isopropyl, n-octyl or benzyl;  
 or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer.  
 
 
     
     
         2 . A pesticide which contains at least one compound of the formula (I) as described in  claim 1  as active compound and at least one auxiliary.  
     
     
         3 . A method for controlling pests wherein a composition as described in  claim 2  is applied to the pests or their habitat.  
     
     
         4 . A process for preparing a composition as described in  claim 2  which contains at least one auxiliary, wherein the active compound is mixed intimately and/or ground with the auxiliary (or auxiliaries).  
     
     
         5 . The use of a compound of the formula (I) as described in  claim 1  for preparing a composition as described in  claim 2 .  
     
     
         6 . The use of a composition as described in  claim 2  for controlling pests.  
     
     
         7 . A method according to  claim 3  for protecting plant propagation material, wherein the propagation material or the location where the propagation material is planted is treated.  
     
     
         8 . Plant propagation material treated in accordance with the method described in  claim 7.