Fused heterocyclic compound

Abstract

This fused heterocyclic compound represented by formula (1) (in the formula, G 1 represents a nitrogen atom or the like, G 2 represents a nitrogen atom or the like, A 1 represents a nitrogen atom or the like, A 2 represents a nitrogen atom or the like, A 3 represents —NR 8 — or the like, A 4 represents a nitrogen atom or the like, A 5 represents a nitrogen atom or the like, R 1 represents a C1-C6 chain hydrocarbon group or the like optionally having one or more atoms or groups selected from a group X, R 2 and R 3 are the same or different and represent a C1-C6 chain hydrocarbon group or the like optionally having one or more atoms or groups selected from the group X, R 8 represents a C1-C6 chain hydrocarbon group or the like optionally having one or more atoms or groups selected from a group W, and n represents 0, 1 or 2.), or an N-oxide thereof, is very effective for pest control.

1 . A fused heterocyclic compound represented by formula (1) or an N-oxide thereof, 
       
         
           
           
               
               
           
         
         wherein 
         G 1  represents a nitrogen atom or ═CR 4 —; 
         G 2  represents a nitrogen atom or ═CR 5 — (wherein at least one of G 1  and G 2  is a nitrogen atom); 
         A 1  represents a nitrogen atom or ═CR 5 —; 
         A 2  represents a nitrogen atom or ═CR 7 —; 
         A 3  represents —NR 8 —, an oxygen atom, or a sulfur atom; 
         A 4  represents a nitrogen atom or ═CR 9 —; 
         A 5  represents a nitrogen atom or ═CR 10 —; 
         R 1  represents a C1 to C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X or a C3 to C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y; 
         R 2  and R 3  are the same or different and represent a C1 to C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, a phenyl group optionally having one or more atoms or groups selected from group Z, a 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z, —OR 11 , —S(O) m R 11 , —S(O) 2 NR 11 R 12 , —NR 11 R 12 , —NR 11 CO 2 R 12 , —NR 11 C(O)R 12 , —CO 2 R 11 , —C(O)R 11 , —C(O)NR 11 R 12 , —SF 5 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; 
         R 4 , R 5 , R 6  and R 7  are the same or different and represent a C1 to C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, a phenyl group optionally having one or more atoms or groups selected from group Z, a 5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z, —OR 13 , —S(O) m R 13 , —S(O) 2 NR 13 R 14 , —NR 13 R 14 , —NR 13 CO 2 R 14 , —NR 13 C(O)R 14 , —CO 2 R 13 , —C(O)R 13 , —C(O)NR 13 R 14 , —SF 5 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; 
         R 8  represents a C1 to C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group W, a C1 to C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group optionally has one or more atoms or groups selected from group Z), a C1 to C6 chain hydrocarbon group having one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group optionally has one or more atoms or groups selected from group Z), —CO 2 R 15 , —C(O)R 15 , a C3 to C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y, or a hydrogen atom; 
         R 9  and R 10  are the same or different and represent a C1 to C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR 16 , —S(O) m R 16 , —NR 16 R 17 , —CO 2 R 16 , —C(O)R 16 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom, R 11 , R 12 , R 13 ; 
         R 14 , R 15 , R 16  and R 17  are the same or different and represent a C1 to C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, or a hydrogen atom; 
         each m independently represents 0, 1, or 2; and 
         n represents 0, 1, or 2; 
         wherein R 2  and R 3  do not simultaneously represent a hydrogen atom or do not simultaneously represent a methyl group; 
         when m is 1 or 2 in —S(O) m R 11 , R 11  does not represent a hydrogen atom; 
         when m is 1 or 2 in —S(O) m R 13 , R 13  does not represent a hydrogen atom; and 
         when m is 1 or 2 in —S(O) m R 16 , R 16  does not represent a hydrogen atom; and 
         wherein: 
         Group X is a group consisting of C1 to C6 alkoxy groups optionally having one or more halogen atoms, C2 to C6 alkenyloxy groups optionally having one or more halogen atoms, C2 to C6 alkynyloxy groups optionally having one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally having one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally having one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally having one or more halogen atoms, C3 to C6 cycloalkyl groups optionally having one or more halogen atoms or one or more C1 to C3 alkyl groups, cyano groups, hydroxy groups, and halogen atoms; 
         Group Y is a group consisting of C1 to C6 chain hydrocarbon groups optionally having one or more halogen atoms, C1 to C6 alkoxy groups optionally having one or more halogen atoms, C2 to C6 alkenyloxy groups optionally having one or more halogen atoms, C2 to C6 alkynyloxy groups optionally having one or more halogen atoms, and halogen atoms; 
         Group Z is a group consisting of C1 to C6 chain hydrocarbon groups optionally having one or more halogen atoms, C1 to C6 alkoxy groups optionally having one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally having one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally having one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally having one or more halogen atoms, C1 to C6 alkylamino groups optionally having one or more halogen atoms, C2 to C8 dialkylamino groups optionally having one or more halogen atoms, halogen atoms, cyano groups, nitro groups, and SF 5 ; and 
         Group W is a group consisting of C1 to C6 alkoxy groups optionally having one or more halogen atoms, C2 to C6 alkenyloxy groups optionally having one or more halogen atoms, C2 to C6 alkynyloxy groups optionally having one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally having one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally having one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally having one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally having one or more halogen atoms, C3 to C6 cycloalkyl groups optionally having one or more halogen atoms, hydroxy groups, halogen atoms, and cyano groups. 
       
     
     
         2 . The fused heterocyclic compound according to  claim 1 , wherein
 A 4  is ═CR 9 —;   R 1  is a C1 to C6 alkyl group optionally having one or more atoms or groups selected from halogen atoms and a cyclopropyl group (wherein the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups), a C2 to C6 alkenyl group optionally having one or more halogen atoms, or a C2 to C6 alkynyl group optionally having one or more halogen atoms;   R 2  is a C1 to C6 alkyl group optionally having one or more halogen atoms, —OR 11  (wherein R 11  is a C1 to C6 alkyl group optionally having one or more halogen atoms), —S(O) m R 11  (wherein R 11  is a C1 to C6 alkyl group optionally having one or more halogen atoms and m is 0, 1 or 2), SF 5 , or a halogen atom;   R 3  is a hydrogen atom;   R 4  and R 5  are the same or different and are a halogen atom or a hydrogen atom;   R 6  is a C1 to C6 alkyl group optionally having one or more halogen atoms, a C2 to C6 alkenyl group optionally having one or more halogen atoms, a C2 to C6 alkynyl group optionally having one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group optionally has one or more atoms or groups selected from a group consisting of halogen atoms, C1 to C3 alkyl groups optionally having a halogen atom and C1 to C3 alkoxy groups optionally having a halogen atom), —OR 13  (wherein R 13  is a C1 to C6 alkyl group optionally having one or more halogen atoms), —S(O) m R 13  (wherein R 13  is a C1 to C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1, or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom;   R 7  is a halogen atom or a hydrogen atom;   R 8  is a C1 to C6 alkyl group optionally having one or more halogen atoms, a C3 to C6 alkenyl group optionally having one or more halogen atoms, a C3 to C6 alkynyl group optionally having one or more halogen atoms, a C1 to C6 alkyl group optionally having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group optionally has one or more atoms or groups selected from a group consisting of halogen atoms, C1 to C3 alkyl groups optionally having a halogen atom and C1 to C3 alkoxy groups optionally having a halogen atom), a C2 to C6 alkoxyalkyl group optionally having one or more halogen atoms, or a hydrogen atom;   R 9  is a hydrogen atom; and   R 10  is a C1 to C6 alkyl group optionally having one or more halogen atoms, —OR 16  (wherein R 16  is a C1 to C6 alkyl group optionally having one or more halogen atoms), —S(O) m R 16  (wherein R 16  is a C1 to C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1, or 2), a halogen atom, or a hydrogen atom, or an N-oxide thereof.   
     
     
         3 . The fused heterocyclic compound according to  claim 1 , wherein
 A 4  is ═CR 9 —;   R 1  is an ethyl group or a cyclopropylmethyl group;   R 2  is a C1 to C6 haloalkyl group, —OR 11  (wherein R 11  is a C1 to C6 haloalkyl group), —S(O) m R 11  (wherein R 11  is a C1 to C6 haloalkyl group, and m is 0, 1, or 2), SF 5 , or a halogen atom;   R 3  is a hydrogen atom;   R 4  and R are a hydrogen atom;   R 6  is a C1 to C6 alkyl group optionally having one or more halogen atoms, —OR 13  (wherein R 13  is a C1 to C6 alkyl group optionally having one or more halogen atoms), —S(O) m R 13  (wherein R 13  is a C1 to C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1, or 2), a halogen atom, or a hydrogen atom;   R 7  is a hydrogen atom;   R 8  is a methyl group, a propargyl group, a methoxymethyl group, or an ethoxymethyl group;   R 9  is a hydrogen atom; and   R 10  is a hydrogen atom or a halogen atom, or an N-oxide thereof.   
     
     
         4 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is ═CR 6 —, or an N-oxide thereof. 
     
     
         5 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is ═CR 6 —, G 1  is a nitrogen atom, and G 2  is ═CR 5 —, or an N-oxide thereof. 
     
     
         6 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is ═CR 6 —, G 1  is a nitrogen atom, G 2  is ═CR 5 —, and A 2  is ═CR 7 —, or an N-oxide thereof. 
     
     
         7 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is ═CR 6 —, G 1  is ═CR 5 —, and G 2  is a nitrogen atom, or an N-oxide thereof. 
     
     
         8 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is ═CR 6 —, and G 1  and G 2  are a nitrogen atom, or an N-oxide thereof. 
     
     
         9 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is a nitrogen atom, or an N-oxide thereof. 
     
     
         10 . The fused heterocyclic compound according to  claim 1 , wherein A 1  is a nitrogen atom, and A 2  is ═CR 7 —, or an N-oxide thereof. 
     
     
         11 . The fused heterocyclic compound according to  claim 1 ,
 wherein   
       
         
           
           
               
               
           
         
         in the formula (1) is J1 to J6 as shown below, 
       
       
         
           
           
               
               
           
         
         [symbols represent the same meaning as in the formula (1)] 
         or an N-oxide thereof. 
       
     
     
         12 . A pest control composition comprising the fused heterocyclic compound or the N-oxide thereof as defined in  claim 1 , and an inert carrier. 
     
     
         13 . A method for controlling pests comprising applying an effective amount of the fused heterocyclic compound or the N-oxide thereof as defined in  claim 1  to a pest or a pest-infested area.