Pesticidally active tetracyclic derivatives with sulphur containing substituents

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds, can be used as insecticides and can be prepared in a manner known per se.

What is claimed is: 
     
         1 . A compound of formula (I), 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are, independently from each other, hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, cyano, nitro, C(O)R 8 , C(O)OR 9 , CONR 10 R 11 , or S(O) m1 R 12 ; 
         R 3  is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 5 halocyloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl or C 3 -C 6 halocycloalkyl-C 1 -C 4 alkyl; 
         R 4  and R 6  are hydrogen, halogen, or C 1 -C 3 alkyl; 
         R 5  is hydrogen, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, or C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, hydroxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy and cyano; or is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 4 alkyl, and halogen; or 
         R 5  is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl; or 
         R 5  is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or 
         R 5  is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, pentafluorosulfanyl, C 1 -C 4 haloalkoxy, —C(O)C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsufinyl, or C 1 -C 4 alkylsulfonyl; or 
         R 5  is pyrimidine or pyridine which both can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsufonyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, and —C(O)C 1 -C 4 alkyl; 
         X is nitrogen or CR 13 ; 
         Y is nitrogen or CR 14 ; 
         G, is nitrogen or CR 15 ; 
         V is nitrogen or CH; 
         Z is nitrogen and G 2  is nitrogen or CR 16 ; or 
         Z is carbon and G 2  is N—R 7 , sulphur, oxygen or CR 16 ; 
         R 7  is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; 
         R 8 , R 9 , R 10 , R 11 , and R 12  independently of one another are hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl, with the proviso that when m 1  is 2, R 12  is different from hydrogen; 
         R 13 , R 14 , R 15  and R 16  are, independently from each other, hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyl substituted by one or more methoxy groups, or R 13 , R 14 , R 15  and R 16  are, independently from each other, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, phenylcarbonylsulfanyl, cyano, mercapto, or C 1 -C 4 alkoxycarbonyl; 
         n is 1 or 2; 
         m is 0, 1 or 2; 
         m 1  is 0, 1 or 2; 
         p is 1, 2, 3 or 4; 
         and agrochemically acceptable salts and N-oxides of those compounds. 
       
     
     
         2 . A compound of formula (I) according to  claim 1 , represented by the compounds of formula (Ia) 
       
         
           
           
               
               
           
         
         wherein; 
         R 1 , R 2 , R 3 , R 5 , R 13 , V, n, and m are as defined under formula (I) in  claim 1  and G 2  is oxygen, sulphur or is nitrogen substituted with hydrogen or with C 1 -C 2 alkyl. 
       
     
     
         3 . A compound of formula (I) according to  claim 1  represented by the compounds of formula (Ib) 
       
         
           
           
               
               
           
         
         wherein 
         R 1 , R 2 , R 3 , R 5 , V, n, and m are as defined under formula (I) in  claim 1 , and G 2  is oxygen, sulphur or nitrogen substituted with hydrogen or with C 1 -C 2 alkyl. 
       
     
     
         4 . A compound of formula (I) according to  claim 1 , represented by the compounds of formula (Ic) 
       
         
           
           
               
               
           
         
         wherein 
         R 1 , R 2 , R 3 , R 5 , V, n, and m are as defined under formula (I) in  claim 1 , G 2  is nitrogen or G 2  is methine or CH—CH 3 . 
       
     
     
         5 . A compound of formula (I) according to  claim 1 , is represented by the compounds of formula (Id) 
       
         
           
           
               
               
           
         
         wherein 
         R 1 , R 2 , R 3 , R 5 , R 12 , V, Y, n and m are as defined under formula (I) in  claim 1 , G 2  is nitrogen or G 2  is methine or CH—CH 3 . 
       
     
     
         6 . A compound of formula (I) according to  claim 1 , wherein
 R 1  is hydrogen or cyano;   R 2  is hydrogen;   R 3  is C 1 -C 4 alkyl;   R 4  is hydrogen;   R 5  is C 1 -C 4 haloalkyl;   R 6  is hydrogen;   p is 1;   n is 1 or 2;   m is 0 or 2;   X is CH;   Y is N;   Z is carbon;   G 1  is N;   G 2  is N—R 7 ;   R 7  is C 1 -C 4 alkyl; and   V is N.   
     
     
         7 . A compound of formula (IIb) 
       
         
           
           
               
               
           
         
         wherein G 1 , G 2 , R 3 , R 4 , R 5 , R 6 , m, V, X, Y and Z have the meanings described under formula (I) in  claim 1  and X 01  is halogen or trifluoromethanesulfonate with the exception of the compounds]; 6-bromo-2-(3-ethylsulfanyl-2-pyridyl)-7-isopropyl-3-methyl-imidazo[4,5-b]pyrdine [1421956-60-6], 6-brom-7-(difluoromethyl)-2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-imidazo[4,5-b]pyridine [1421956-59-3], 6-bromo-7-(difluoromethyl)-2-(3-ethylsulfinyl-2-pyridyl)-3-methyl-imidazo[4,5-b]pyridine [1421956-58-2], 6-bromo-7-(difluoromethyl)-2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-imidazo[4,5-b]pyridine [1421956-57-1], 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-6-iodo-3-methyl-imidazo[4,5-b]pyridine [1421956-26-4], 6-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-imidazo[4,5-b]pyridine [1421956-07-1], 6-bromo-2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-imidazo[45-b]pyridine [1421956-06-0], 6-bromo-2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-imidazo[45-b]pyridine [1421956-04-8], 6-bromo-2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-imidazo[4,5-b]pyridine-7-carbaldehyde [1421954-62-2], 6-bromo-2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-imidazo[4,5-b]pyridine [1421954-25-7], 2-(3-ethylsulfonyl-2-pyridyl)-6-iodo-3-methyl-imidazo[4,5-b]pyridine [1421950-96-0], 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-5-iodo-1-methyl-benzimidazole [1421950-48-2], 2-(3-ethylsulfanyl-2-pyridyl)-5-iodo-1-methyl-benzimidazole [1421950-16-4], 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-5-iodo-1,3-benzoxazole [1616682-41-7], 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-5-iodo-1,3-benzoxazole [1616682-43-9], 6-bromo-2-(5-bromo-3-ethylsulfonyl-2-pyridyl)oxazolo[5,4-b]pyridine [1616682-28-0], 6-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]oxazolo[5,4-b]pyridine [1616682-16-6], 5-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-1,3-benzoxazole [1616682-19-9], 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-6-iodo-thiazolo[5,4-b]pyridine [1421956-35-5], and 2-[2-ethylsulfanyl-4-(trifluoromethyl)phenyl]-6-iodo-thiazolo[5,4-b]pyridine [1383947-33-8]. 
       
     
     
         8 . A compound of formula (III), 
       
         
           
           
               
               
           
         
         wherein G 1 , G 2 , R 3 , R 4 , R 5 , R 6 , m, V, X, Z and Y have the definitions as described under formula (I) in  claim 1 . 
       
     
     
         9 . A pesticidal composition, which comprises at least one compound of formula I according to  claim 1  or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary. 
     
     
         10 . A method for controlling pests, which comprises applying a composition according to  claim 8  to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body. 
     
     
         11 . A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to  claim 9 . 
     
     
         12 . Plant propagation material treated in accordance with the method described in  claim 11 . 
     
     
         13 . A substrate selected from nonwoven and fabric material comprising a composition according to  claim 9 .