Insecticidal compounds

Abstract

A compound of formula (I): wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.

1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         A 1 , A 2 , A 3  and A 4  are independently of one another C—H, C—R 5 , or nitrogen; 
         G 1  is oxygen or sulfur; 
         L is a single bond, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, or C 2 -C 8 haloalkynyl; 
         R 1  is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, or C 1 -C 8 alkoxycarbonyl-; 
         R 2  is hydrogen, or C 1 -C 8 alkyl; 
         R 3  is C 1 -C 8 haloalkyl; 
         R 4  is aryl or aryl substituted by one to three R 6 , or heterocyclyl or heterocyclyl substituted by one to three R 6 ; 
         Y 1 , Y 2  and Y 3  are independently of another CR 7 R 8 , C═O, C═N—OR 9 , N—R 9 , S, SO, SO 2 , S═N—R 9 , or SO═N—R 9 , provided that at least one of Y 1 , Y 2  or Y 3  is not CR 7 R 8 ; 
         each R 5  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkoxycarbonyl-, aryl or aryl optionally substituted by one to three R 10 , or heteroaryl or heteroaryl optionally substituted by one to three R 10 , or where two R 5  are adjacent, the two R 5  may together with the carbon atoms to which the two R 5  are bonded form a 5-membered ring, wherein the 5-membered ring is —OCH═N—, —SCH═N—, —OCR 10 ═N—, or —SCR 10 ═N—; 
         each R 6  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-; 
         each R 7  and R 8  is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl; 
         each R 9  is independently hydrogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkyl-carbonyl-, C 1 -C 8 haloalkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, C 1 -C 8 haloalkoxycarbonyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, aryl-C 1 -C 4 alkyl- or aryl-C 1 -C 4 alkyl- wherein the aryl moiety is substituted by one to three R 11 , or heteroaryl-C 1 -C 4 alkyl- or heteroaryl-C 1 -C 1 alkyl- wherein the heteroaryl moiety is substituted by one to three R 11 ; 
         each R 10  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-; and 
         each R 11  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-; or a salt or N-oxide thereof. 
       
     
     
         2 . A compound according to  claim 1  wherein A 1  is C—H or C—R 5 . 
     
     
         3 . A compound according to  claim 1  wherein A 2  is C—H or C—R 5 . 
     
     
         4 . A compound according to  claim 1  wherein A 3  is C—H or C—R 5 . 
     
     
         5 . A compound according to  claim 1  wherein A 4  is C—H or C—R 5 . 
     
     
         6 . A compound according to  claim 1  wherein G 1  is oxygen. 
     
     
         7 . A compound according to  claim 1  wherein L is a single bond, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl. 
     
     
         8 . A compound according to  claim 1  wherein R 1  is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-. 
     
     
         9 . A compound according to  claim 1  wherein R 2  is hydrogen or methyl. 
     
     
         10 . A compound according to  claim 1  wherein R 3  is chlorodifluoromethyl or trifluoromethyl. 
     
     
         11 . A compound according to  claim 1  wherein R 4  is aryl or aryl substituted by one to three R 6 . 
     
     
         12 . A compound according to  claim 1  wherein Y 1 , Y 2  and Y 3  are independently of another CR 7 R 8 , C═O, C═N—OR 9 , N—R 9 , S, SO, SO 2 , S═N—R 9 , or SO═N—R 9 , provided that one of Y 1 , Y 2  or Y 3  is not CR 7 R 8 . 
     
     
         13 . A compound according to  claim 1  wherein each R 5  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-. 
     
     
         14 . A compound according to  claim 1  wherein each R 7  and R 8  is independently hydrogen or methyl. 
     
     
         15 . A compound according to  claim 1  wherein each R 9  is independently hydrogen, cyano, methyl, trifluoromethyl, methylcarbonyl-, trifluoromethylcarbonyl-, methoxycarbonyl-, trifluoromethoxycarbonyl-, methylsulfonyl-, trifluoromethylsulfonyl-, or benzyl or benzyl wherein the phenyl moiety is substituted by one to three R 10 . 
     
     
         16 . A compound of formula (XI) 
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XI′) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XII) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XIII) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1  and X B  is halogen; or a salt or N-oxide thereof; or
 a compound of formula (XIV) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XV) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XVIII) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XIX) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XX) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XXII) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XXIII) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , Y 1 , Y 2  and Y 3  are as defined in  claim 1  and Hal is a halogen; or a salt or N-oxide thereof; or
 a compound of formula (XXIV) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof; or
 a compound of formula (XXIV′) 
 
       
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2  and Y 3  are as defined in  claim 1 ; or a salt or N-oxide thereof. 
       
     
     
         17 . A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in  claim 1 . 
     
     
         18 . An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in  claim 1 .