Insecticidal triazinone derivatives

Abstract

Compounds of the formula I or I′ wherein the substituents are as defined in claim 1 , are useful as pesticides.

1 . A compounds of the formula (IIa): 
       
         
           
           
               
               
           
         
         Wherein, 
         R 1  is either Q 1 , Q 2 , or Q 3   
       
       
         
           
           
               
               
           
         
         X is O, S, or NR 5  wherein R 5  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 
         A 1  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenylC 1 -C 5 alkylcarbonyl, phenylcarbonyl, C 1 -C 6 alkylsulfonyl, phenylsulfonyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by 0 or S, C 3 -C 6 cycloalkylcarbonyl, wherein a ring methylene group may optionally be replaced by O or S, or C 3 -C 6 cycloalkylC 1 -C 4 alkylcarbonyl, wherein a ring or chain methylene group may optionally be replaced by O or S; 
         A 2  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkyloxy, hydroxy, amino; 
         B 1  is CR 6 R 7 , or C(O), S(O) m , wherein m is 1 or 2 
         B 2  is CR 8 R 9 , O, NR 10  wherein R 10  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl; 
         C 1  is CR 11 R 12 , C(O); 
         C 2  is CR 13 R 14 ; 
         C 3  is CR 15 R 16 , O, NR 17 ; wherein R 17  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl, 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  are each independently of the other hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, or 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  form a 3-6-membered carbocycle wherein a ring methylene group may optionally be replaced by O or S, 
         wherein the phenyl and the heteroaryl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro. 
       
     
     
         2 . A compound according to  claim 1 , wherein the compound is a compound of formula: 
       
         
           
           
               
               
           
         
       
     
     
         3 . A compound of formula (VIIIa) 
       
         
           
           
               
               
           
         
         wherein R 1  is either Q 1 , Q 2 , or Q 3   
       
       
         
           
           
               
               
           
         
         Wherein, 
         X is O, S, or NR 5  wherein R 5  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 
         A 1  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 6 alkoxycarbonyl, phenylC 1 -C 6 alkylcarbonyl, phenylcarbonyl, C 1 -C 6 alkylsulfonyl, phenylsulfonyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylcarbonyl, wherein a ring methylene group may optionally be replaced by O or S, or C 3 -C 6 cycloalkylC 1 -C 4 alkylcarbonyl, wherein a ring or chain methylene group may optionally be replaced by O or S; 
         A 2  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkyloxy, hydroxy, amino; 
         B 1  is CR 6 R 7 , or C(O), S(O) m , wherein m is 1 or 2 
         B 2  is CR 8 R 9 , O, NR 10  wherein R 19  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl; 
         C 1  is CR 11 R 12 , C(O); 
         C 2  is CR 13 R 14 ; 
         C 3  is CR 15 R 16 , O, NR 17 ; wherein R 17  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl, 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  are each independently of the other hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, or 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  form a 3-6-membered carbocycle wherein a ring methylene group may optionally be replaced by O or S, 
         wherein the phenyl and the heteroaryl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro, 
         and Ra is C 1 -C 6 alkyl. 
       
     
     
         4 . A compound of formula (V) 
       
         
           
           
               
               
           
         
         Wherein Ra is C 1 -C 6 alkyl. 
       
     
     
         5 . A compound of formula (VI): 
       
         
           
           
               
               
           
         
         wherein R 1  is either Q 1 , Q 2 , or Q 3   
       
       
         
           
           
               
               
           
         
         Wherein, 
         X is O, S, or NR 5  wherein R 5  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 
         A 1  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenylC 1 -C 5 alkylcarbonyl, phenylcarbonyl, C 1 -C 6 alkylsulfonyl, phenylsulfonyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylcarbonyl, wherein a ring methylene group may optionally be replaced by O or S, or C 3 -C 6 cycloalkylC 1 -C 4 alkylcarbonyl, wherein a ring or chain methylene group may optionally be replaced by O or S; 
         A 2  is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkyloxy, hydroxy, amino; 
         B 1  is CR 6 R 7 , or C(O), S(O) m , wherein m is 1 or 2 
         B 2  is CR 8 R 9 , O, NR 10  wherein R 19  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl; 
         C 1  is CR 11 R 12 , C(O); 
         C 2  is CR 13 R 14 ; 
         C 3  is CR 15 R 16 , O, NR 17 ; wherein R 17  is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl, 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  are each independently of the other hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, or 
         wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16  form a 3-6-membered carbocycle wherein a ring methylene group may optionally be replaced by O or S, 
         wherein the phenyl and the heteroaryl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro.