Isoxazoline derivatives as insecticides

Abstract

The present invention relates to compounds formula (I): wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 17 , R 18 , R 19 and R 20 are as defined herein; 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, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

1 . A compound of formula Int-III 
       
         
           
           
               
               
           
         
         wherein 
         Q is phthalimidyl, hydroxy, or a leaving group; 
         A 1 , A 2 , A 3  and A 4  are independently of each other C—H, C—R 7 , or nitrogen; 
         R 3  is C 1 -C 8 haloalkyl; 
         R 4  is aryl or aryl substituted by one to five R 11 , heteroaryl or heteroaryl substituted by one to five R 11 ; 
         R 5  is hydrogen; 
         R 6  is hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 12 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 13 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene- wherein the aryl moiety is substituted by one to five R 14 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 14 , aryl or aryl substituted by one to five R 14 , heterocyclyl or heterocyclyl substituted by one to five R 14 , C 1 -C 4 alkoxycarbonyl-, C 1 -C 4 alkenyloxycarbonyl-, C 1 -C 4 alkynyloxycarbonyl-, or benzyloxycarbonyl- or benzyloxycarbonyl- in which the benzyl group is optionally substituted by one to five R 16 ; 
         each R 7  is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkenyl, C 1 -C 8 haloalkenyl, C 1 -C 8 alkynyl, C 1 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, or C 1 -C 8 haloalkylsulfonyl-; 
         each R 8  is independently halogen, cyano, nitro, hydroxy, amino, C 1 -C 8 alkylamino, (C 1 -C 8 alkyl) 2 amino, C 1 -C 8 alkylcarbonylamino, C 1 -C 8 haloalkylcarbonylamino, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, aryloxy or aryloxy substituted by one to five R 15 , aryloxy-C 1 -C 4 alkylene or aryloxy-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 15 , C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, mercapto, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, or aryl-C 1 -C 4 alkylthio- or aryl-C 1 -C 4 alkylthio- wherein the aryl moiety is substituted by one to five R 15 ; 
         each R 9  is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 alkenyl, C 1 -C 8 alkynyl, C 1 -C 8 alkyl-O—N═, C 1 -C 8 haloalkyl-O—N═, C 1 -C 8 alkoxy or C 1 -C 8 alkoxycarbonyl; 
         each R 11  and R 14  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, hydroxy, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, mercapto, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, aryl or aryl substituted by one to five R 15 , or heterocyclyl or heterocyclyl substituted by one to five R 15 ; 
         each R 12  is independently halogen, cyano, nitro, hydroxy, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, mercapto, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, or C 1 -C 8 haloalkylsulfonyl-; 
         each R 13  is independently halogen or C 1 -C 8 alkyl; 
         each R 15  is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy-, or C 1 -C 4 haloalkoxy-; 
         each R 16  is independently halogen, cyano, formyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl; and 
         R 17  and R 18  are independently hydrogen, halogen, C 1 -C 12 alkyl or C 1 -C 12 alkyl substituted by one to five R 8 , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to five R 9 , C 2 -C 12 alkenyl or C 2 -C 12 alkenyl substituted by one to five R 8 , C 2 -C 12 alkynyl or C 2 -C 12 alkynyl substituted by one to five R 8 , cyano, C 1 -C 12 alkoxycarbonyl or C 1 -C 12 alkoxycarbonyl substituted by one to five R 8 , C 1 -C 12 alkoxythiocarbonyl or C 1 -C 12 alkoxythiocarbonyl substituted by one to five R 8 , or R 17  and R 18  together with the carbon atom to which they are attached may form a 3 to 6-membered carbocyclic ring; 
         or a salt or N-oxide thereof.