Condensed heterocyclic compounds and pesticides

Abstract

To provide novel pesticides, especially insecticides or acaricides. A condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with —S(O) n R 1 is a ring represented by any one of D1, D2 and D3, Q is a ring represented by any one of Q1, Q2, Q3 and Q4, R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 1a , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkyl (C 1 -C 6 ) alkyl, C 3 -C 6 halocycloalkyl (C 1 -C 6 ) alkyl or hydroxy (C 1 -C 6 ) alkyl, R 1a is C 1 -C 8 alkoxycarbonyl, and n is an integer of 0, 1 or 2.

1 - 25 . (canceled) 
     
     
         26 . A condensed heterocyclic compound represented by The following formula or its salt or an N-oxide thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         G 1  is a nitrogen atom or C(Y1); 
         G 2  is a nitrogen atom or C(Y2); 
         G 3  is a nitrogen atom or C(Y3); 
         G 4  is a nitrogen atom or C(Y4); 
         A 8  is a nitrogen atom or C(R 8 ); 
         R 1  is C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 1a , C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 2 -C 6  haloalkynyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 3 -C 6  cycloalkyl (C 1 -C 6 ) alkyl, C 3 -C 6  halocycloalkyl (C 1 -C 6 ) alkyl or hydroxy (C 1 -C 6 ) alkyl; 
         R 1a  is C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, C 1 -C 8  alkoxycarbonyl, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl or cyano; 
         R 6  is a hydrogen atom, a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, —C(O)R 60a , —C(O)OH, hydroxy, —NH 2 , —NHR 60g , —N(R 60h )R 60g , mercapto, cyano or nitro; 
         R 7  is a hydrogen atom, a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, mercapto, —SF 5 , cyano or nitro; 
         R 8  is a hydrogen atom, a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy or cyano; 
         each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, (C 1 -C 6 ) alkyl optionally substituted with Y a , (C 1 -C 6 ) haloalkyl optionally substituted with Y a , C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, (C 2 -C 6 ) alkenyl optionally substituted with Y a , C 2 -C 6  alkynyl, C 2 -C 6  haloalkynyl, (C 2 -C 6 ) alkynyl optionally substituted with Y b , C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, (C 1 -C 8 ) alkoxy optionally substituted with Y a , C 2 -C 6  alkenyloxy, C 2 -C 6  haloalkenyloxy, (C 2 -C 6 ) alkenyloxy optionally substituted with Y a , C 2 -C 6  alkynyloxy, C 2 -C 6  haloalkynyloxy, (C 2 -C 6 ) alkynyloxy optionally substituted with Y a , C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 3 -C 6  cycloalkyl (C 1 -C 6 ) alkyl, C 3 -C 6  halocycloalkyl (C 1 -C 6 ) alkyl, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, (C 1 -C 6 ) alkylthio optionally substituted with Y a , C 2 -C 6  alkenylthio, C 2 -C 6  haloalkenylthio, C 2 -C 6  alkynylthio, C 2 -C 6  haloalkynylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, (C 1 -C 6 ) alkylsulfinyl optionally substituted with Y a , C 2 -C 6  alkenylsulfinyl, C 2 -C 6  haloalkenylsulfinyl, C 2 -C 6  alkynylsulfinyl, C 2 -C 6  haloalkynylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, (C 1 -C 6 ) alkylsulfonyl optionally substituted with Y a , C 2 -C 6  alkenylsulfonyl, C 2 -C 6  haloalkenylsulfonyl, C 2 -C 6  alkynylsulfonyl, C 2 -C 6  haloalkynylsulfonyl, —C(O)R 90a , —C(O)NHR 90b , —C(O)N(R 90c )R 90b , —C(O)OH, —C(═NOR 90d )R 90a , —C(O)NH 2 , hydroxy, —OC(O)R 90e , —OS(O) 2 R 90f , —NH 2 , —NHR 90g , —N(R 90h )R 90g , mercapto, —SC(O)R 90i , —S(O) 2 NHR 90j , —S(O) 2 N(R 90k )R 90j , —SF 5 , cyano, nitro, phenyl, phenyl optionally substituted with Y c , heterocyclyl or heterocyclyl optionally substituted with Y c ; 
         Y a  is C 1 -C 3  alkoxy, C 1 -C 8  haloalkoxy, C 1 -C 8  alkoxycarbonyl, C 1 -C 8  haloalkoxycarbonyl, C 1 -C 6  alkylcarbonyl, C 1 -C 6  haloalkylcarbonyl, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, hydroxy or cyano; 
         Y b  is C 1 -C 6  alkyl, C 3 -C 6  cycloalkyl, trimethylsilyl or phenyl; 
         Y c  is a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, cyano or nitro; 
         each of R 60a  and R 90a  is independently a hydrogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy or C 1 -C 8  haloalkoxy; 
         each of R 60g , R 60h , R 90b , R 90c , R 90i , R 90j  and R 90k  is independently C 1 -C 6  alkyl or C 1 -C 6  haloalkyl; 
         R 90d  is a hydrogen atom, C 1 -C 6  alkyl or C 1 -C 6  haloalkyl; 
         R 90e  is a hydrogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, C 1 -C 6  alkylamino, C 1 -C 6  haloalkylamino, di(C 1 -C 6 ) alkylamino or di(C 1 -C 6 ) haloalkylamino; 
         R 90f  is C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkylamino, C 1 -C 6  haloalkylamino, di(C 1 -C 6 ) alkylamino or di(C 1 -C 6 ) haloalkylamino; 
         each of R 90g  and R 90h  is independently C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkylcarbonyl, C 1 -C 6  haloalkylcarbonyl, C 1 -C 5  alkoxycarbonyl, C 1 -C 8  haloalkoxycarbonyl, C 1 -C 6  alkylaminocarbonyl, C 1 -C 6  haloalkylaminocarbonyl, C 1 -C 6  alkylaminothiocarbonyl, C 1 -C 6  haloalkylaminothiocarbonyl, phenylcarbonyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, C 1 -C 6  alkylaminosulfonyl or di(C 1 -C 6 ) alkylaminosulfonyl; and 
         n is an integer of 0, 1 or 2. 
       
     
     
         27 . The condensed heterocyclic compound or its salt or an N-oxide thereof according to  claim 26 , wherein:
 G 1  is C(Y1);   G 2  is C(Y2);   G 3  is C(Y3);   G 4  is C(Y4);   R 1  is C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 2 -C 6  haloalkynyl, C 3 -C 6  cycloalkyl (C 1 -C 6 ) alkyl or C 3 -C 6  halocycloalkyl (C 1 -C 6 ) alkyl;   each of R 6  and R 8  is independently a hydrogen atom, a halogen atom, C 1 -C 6  alkyl or C 1 -C 6  haloalkyl;   R 7  is a hydrogen atom, a halogen atom or C 1 -C 6  haloalkyl;   each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with Y b , C 1 -C 8  alkoxy, C 1 -C 8  haloalkoxy, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, (C 1 -C 6 ) alkylthio optionally substituted with Y a , C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, —C(O)R 90a , —C(O)NHR 90b , —C(O)N(R 90c )R 90b , —C(O)OH, hydroxy, —OC(O)R 90e , —OS(O) 2 R 90f , —NH 2 , —NHR 90g , —N(R 90h )R 90g , mercapto, —SC(O)R 90i , —S(O) 2 NHR 90j , —S(O) 2 N(R 90k )R 90j , —SF 5 , cyano, nitro, phenyl, phenyl optionally substituted with Y c , heterocyclyl or heterocyclyl optionally substituted with Y c ; and   Y a  is C 1 -C 8  alkoxycarbonyl.   
     
     
         28 . The condensed heterocyclic compound or its salt or an N-oxide thereof according to  claim 27 , wherein:
 R 1  is C 1 -C 6  alkyl;   R 6  is a hydrogen atom;   R 7  is C 1 -C 6  haloalkyl;   R 8  is a hydrogen atom or C 1 -C 6  alkyl;   each of Y1 and Y4 is a hydrogen atom;   Y2 is a hydrogen atom, a halogen atom or C 1 -C 6  haloalkyl; and   Y3 is a hydrogen atom or C 1 -C 6  haloalkyl.   
     
     
         29 . The condensed heterocyclic compound or its salt or an N-oxide thereof according to  claim 27 , wherein:
 R 6  is a hydrogen atom;   each of Y1 and Y4 is a hydrogen atom; and   each of Y2 and Y3 is independently a hydrogen atom or C 1 -C 6  haloalkyl.   
     
     
         30 . The condensed heterocyclic compound or its salt or an N-oxide thereof according to  claim 26 , wherein:
 G 1  is C(Y1);   G 2  is C(Y2);   G 3  is C(Y3);   G 4  is C(Y4); and   n is 2.   
     
     
         31 . The condensed heterocyclic compound or its salt or an N-oxide thereof according to  claim 30 , wherein:
 each of Y1, Y3 and Y4 is a hydrogen atom;   Y2 is C 1 -C 6  haloalkyl;   As is a nitrogen atom;   R 1  is C 1 -C 6  alkyl;   R 6  is a hydrogen atom; and   R 7  is a C 1 -C 6  haloalkyl.   
     
     
         32 . An agricultural chemical composition, comprising:
 the condensed heterocyclic compound of  claim 26  or its salt or N-oxide as an active ingredient; and   an agriculturally acceptable diluent.   
     
     
         33 . A method for treating internal or external parasites in or on a mammal or bird, comprising:
 administering the condensed heterocyclic compound of  claim 26  or its salt or N-oxide to the mammal or bird.   
     
     
         34 . The method according to  claim 31 , wherein the external parasites are Siphonaptera or ticks. 
     
     
         35 . A method for treating a seed, comprising:
 applying the condensed heterocyclic compound of  claim 26  or its salt or N-oxide to the seed.   
     
     
         36 . A method for treating soil, comprising:
 applying the condensed heterocyclic compound of  claim 26  or its salt or N-oxide to soil.