Condensed heterocylic compounds and herbicides containing them as active ingredients

Abstract

Condensed heterocyclic compounds of the general formula: wherein T is carbon or nitrogen; when T is carbon, then the bond between T and A is a double bond, the bond between A and Y is a single bond, and Y is oxygen, sulfur, or optionally substituted NH; or when T is nitrogen, then the bond between T and A is a single bond, the bond between A and Y is a double bond, and Y is nitrogen or optionally substituted CH; A is nitrogen or optionally substituted CH; R 1 is hydrogen, halogen, alkyl, haloalkyl, hydroxymethyl, nitro, or cyano; R 2 is hydrogen, halogen, alkyl, haloalkyl, hydroxymethyl, nitro, cyano, or the like; R 3 is hydrogen, halogen, alkyl, haloalkyl, hydroxymethyl, nitro, cyano, or the like; R 4 is hydrogen, halogen, alkyl, haloalkyl, hydroxymethyl, nitro, or cyano, and Q is a saturated or unsaturated 5- or 6-membered heterocyclic ring containing one to four nitrogen atoms, or a saturated or unsaturated cyclopentylideneamino group containing one or two nitrogen heteroatoms and one oxygen or sulfur heteroatom.

1 . A condensed heterocyclic compound of general formula I:  
       
         
           
           
               
               
           
         
         wherein T is carbon, the bond between T and A is a double bond, the bond between A and Y is a single bond, and Y is oxygen,;  
         A is nitrogen;  
         R 1  is hydrogen, halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, hydroxymethyl, nitro, or cyano;  
         R 2  is hydrogen, halogen, C 1 -C 11  alkyl, C 1 -C 11  haloalkyl, hydroxymethyl, nitro, cyano, —N(R 9 )R 10 , —OR 11 , —SR 12 , —SO 2 R 13 , —COX, —COOR 14 , —CON(R 15 )R 16 , —COR 17 , —C(R 26 )═NOR 19 , —C(R 27 )═C(R 21 )R 22 , or —CH(R 23 )—CH(R 24 )R 25 ;  
         R 3  is hydrogen, halogen, C 1 -C 11  alkyl, C 1 -C 11  haloalkyl, hydroxymethyl, nitro, cyano, —N(R 50 )R 60 , —OR 61 , —SR 62 , —SO 2 R 63 , —COX, —COOR 64 , —CON(R 65 )R 66 , —COR 67, —C(R 76 )═NOR 69 , —C(R 77 )═C(R 71 )R 72 , or —CH(R 73 )—CH(R 74 )R 75 ;  
         R 4  is hydrogen, halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, hydroxymethyl, nitro, or cyano;  
         wherein X is chlorine or bromine;  
         R 9  and R 59  are independently hydrogen, C 1 -C 5  alkyl, (C 1 -C 5  alkyl)carbonyl, or (C 1 -C 5  alkoxy)carbonyl;  
         R 10 , R 11 , and R 12  are independently hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10  halocycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10  alkenyl, C 3 -C 10  haloalkenyl, C 3 -C 10  alkynyl, C 3 -C 10  haloalkynyl, cyano C 1 -C 6  alkyl, (C 1 -C 5  alkyl)carbonyl, (C 1 -C 5  haloalkyl)carbonyl, (C 3 -C 10  cycloalkyl)carbonyl, (C 1 -C 5  alkyl)carbonyl C 1 -C 5  alkyl, (C 1 -C 5  haloalkyl)carbonyl C 1 -C 5  alkyl, hydroxy C 1 -C 5  alkyl, C 1 -C 5  alkoxy C 1 -C 5  alkyl, C 1 -C 5  alkylthio C 1 -C 5  alkyl, (C 1 -C 5  alkoxy)carbonyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl, —C(R 43 )(R 44 )—C(═O)ON(R 45 )R 46 , —C(R 47 )(R 48 )—CON(R 49 )R 50 , —CH 2 —C(R 56 )═N—OR 55 , —CHMe—C(R 58 )=NOR 57 , (C 3 -C 10  alkenoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkynoxy)carbonyl C 1 -C 5  alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy (C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkenoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkynoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, carboxy(C 1 -C 5  alkyl)carbonyl, (C 1 -C 10  alkoxy)carbonyl(C 1 -C 5  alkyl)carbonyl, (C 1 -C 10  haloalkoxy)carbonyl(C 1 -C 5  alkyl)carbonyl, C 1 -C 5  alkylsulfonyl, C 1 -C 5  haloalkylsulfonyl, —SO 2 N(R 5 )R 52 , —CON(R 53 )R 54 , optionally substituted benzyl, or optionally substituted phenyl;  
         R 60 , R 61 , and R 62  are independently hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10  halocycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10  alkenyl, C 3 -C 10  haloalkenyl, C 3 -C 10  alkynyl, C 3 -C 10  haloalkynyl, cyano C 1 -C 6  alkyl, (C 1 -C 5  alkyl)carbonyl, (C 1 -C 5  haloalkyl)carbonyl, (C 3 -C 10  cycloalkyl)carbonyl, (C 1 -C 5  alkyl)carbonyl C 1 -C 5  alkyl, (C 1 -C 5  haloalkyl)carbonyl C 1 -C 5  alkyl, hydroxy C 1 -C 5  alkyl, C 1 -C 5  alkoxy C 1 -C 5  alkyl, C 1 -C 5  alkylthio C 1 -C 5  alkyl, (C 1 -C 5  alkoxy)carbonyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl, —C(R 163 )(R 164 )—C(═O)ON(R 165 )R 166 , —C(R 167 )(R 168 )—CON(R 169 )R 170 , —CH 2 —C(═NOR 175 )R 176 , —CHMe—C(═NOR 177 )R 178 , (C 3 -C 10  alkenoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkynoxy)carbonyl C 1 -C 5  alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl  
         C 1 -C 5  alkyl, (C 3 -C 10  alkenoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl,  
         (C 3 -C 10  alkynoxy)carbonyl(C 1 -C 5  alkoxy)carbonyl C 1 -C 5  alkyl, carboxy(C 1 -C 5  alkyl)carbonyl, (C 1 -C 10  alkoxy)carbonyl(C 1 -C 5  alkyl)carbonyl, (C 1 -C 10  haloalkoxy)carbonyl(C 1 -C 5  alkyl)carbonyl, C 1 -C 5  alkylsulfonyl, C 1 -C 5  haloalkylsulfonyl, —SO 2 N(R 171 )R 172 , —CON(R 173 )R 174 , optionally substituted benzyl, or optionally substituted phenyl;  
         wherein R 43 , R 44 , R 163 , and R 164  are independently hydrogen, halogen, C 1 -C 5  alkyl, or C 1 -C 5  haloalkyl;  
         R 45 , R 46 , R 165 , and R 166  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 45  and R 46  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring, or R 165  and R 166  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;  
         R 47 , R 48 , R 167 , and R 168  are independently hydrogen, halogen, C 1 -C 5  alkyl, or C 1 -C 5  haloalkyl;  
         R 49 , R 50 , R 169 , and R 170  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 49  and R 50  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R 169  and R 170  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 51 , R 52 , R 171 , and R 172  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 51  and R 52  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R 171  and R 172  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 53 , R 54 , R 173 , and R 174  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 53  and R 54  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R 173  and R 174  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 55 , R 57 , R 175 , and R 177  are independently hydrogen or C 1 -C 3  alkyl;  
         R 56 , R 58 , R 176 , and R 178  are independently hydrogen, C 1 -C 5  alkyl, (C 1 -C 5  alkoxy)carbonyl, (C 1 -C 5  haloalkoxy)carbonyl, (C 3 -C 5  cycloalkoxy)carbonyl, (C 3 -C 5  alkenoxy)carbonyl, or (C 3 -C 5  alkynoxy)carbonyl;  
         R 13  is hydroxy, chlorine, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl, —N(R 79 )R 80 , or —OR 81 ;  
         R 63  hydroxy, chlorine, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl, —N(R 179 )R 180 , or —OR 181 ;  
         wherein R 79  and R 179  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10 cycloalkoxy)carbonyl C 1 -C 5  alkyl, or (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl; R 80  and R 180  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 79  and R 80  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R 179  and R 180  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; and R 81  and R 181  are independently C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, or (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl;  
         R 14  is hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10 halocycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10 alkenyl, C 3 -C 10  haloalkenyl, C 3 -C 10 alkynyl, C 3 -C 10  haloalkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkenoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkynoxy)carbonyl C 1 -C 5  alkyl, —N(R 82 )R 83 , optionally substituted benzyl, or optionally substituted phenyl;  
         R 64  is hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10  halocycloalkyl, C 3 -C 11  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10 alkenyl, C 3 -C 10  haloalkenyl, C 3 -C 10  alkynyl, C 3 -C 10  haloalkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 11  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10 halocycloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkenoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  alkynoxy)carbonyl C 1 -C 5  alkyl, —N(R 182 )R 183 , optionally substituted benzyl, or optionally substituted phenyl;  
         wherein R 82  and R 182  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, or (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl; R 83  and R 183  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 82  and R 83  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R 182  and R 183  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 15  and R 65  are independently hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10  alkenyl, C 3 -C 10  alkynyl, cyano C 1 -C 6  alkyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, optionally substituted benzyl, or optionally substituted phenyl; R 16  and R 66  are independently hydrogen, C 1 -C 10  alkyl, or C 1 -C 10  haloalkyl; or R 15  and R 16  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R 65  and R 66  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 17 , R 26 , R 27 , R 67 , R 76 , and R 77  are independently hydrogen, cyano,  
         C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, (C 1 -C 6  alkoxy)carbonyl, or (C 1 -C 6  alkoxy)carbonylmethyl;  
         R 19  and R 69  are independently hydrogen, C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, C 3 -C 10  halocycloalkyl, C 3 -C 10  cycloalkyl C 1 -C 3  alkyl, C 3 -C 10  alkenyl, C 3 -C 10  haloalkenyl, C 3 -C 10  alkynyl, C 3 -C 10  haloalkynyl, cyano C 1 -C 6  alkyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, or  
         (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl;  
         R 21  and R 71  are independently hydrogen, halogen, C 1 -C 3  alkyl, or C 1 -C 3  haloalkyl;  
         R 22  and R 25  are independently carboxy, (C 1 -C 10  alkoxy)carbonyl,  
         (C 1 -C 10  haloalkoxy)carbonyl, (C 3 -C 10  cycloalkoxy)carbonyl, (C 3 -C 10  halocycloalkoxy)carbonyl, carboxy(C 1 -C 5  alkoxy)carbonyl, (C 1 -C 10  alkoxy)carbonyl  
         (C 1 -C 5  alkoxy)carbonyl, (C 1 -C 10  haloalkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  cycloalkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  alkenoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  alkynoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, —CON(R 84 )R 85 , or —C(═O)ON(R 6 )R 87 ;  
         R 72  and R 75  are independently carboxy, (C 1 -C 10  alkoxy)carbonyl,  
         (C 1 -C 10  haloalkoxy)carbonyl, (C 3 -C 10  cycloalkoxy)carbonyl, (C 3 -C 10  halocycloalkoxy)carbonyl, carboxy(C 1 -C 5  alkoxy)carbonyl, (C 1 -C 10  alkoxy)carbonyl  
         (C 1 -C 5  alkoxy)carbonyl, (C 1 -C 10  haloalkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  cycloalkoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  alkenoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, (C 3 -C 10  alkynoxy)carbonyl (C 1 -C 5  alkoxy)carbonyl, —CON(R 184 )R 185 , or —C(═O)ON(R 186 )R 187 ;  
         wherein R 84  and R 184  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, or (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl; R 85  and R 85  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 84  and R 85  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R 184  and R 185  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;  
         R 86  and R 186  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, carboxy C 1 -C 5  alkyl, (C 1 -C 10  alkoxy)carbonyl C 1 -C 5  alkyl, (C 1 -C 10  haloalkoxy)carbonyl C 1 -C 5  alkyl, (C 3 -C 10  cycloalkoxy)carbonyl C 1 -C 5  alkyl, or (C 3 -C 10  halocycloalkoxy)carbonyl C 1 -C 5  alkyl; R 87  and R1 87  are independently hydrogen, C 1 -C 5  alkyl, C 1 -C 5  haloalkyl, C 3 -C 8  cycloalkyl, C 3 -C 6  alkenyl, or C 3 -C 6  alkynyl; or R 86  and R 87  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring; or R 186  and R 187  may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;  
         R 23 , R 24 , R 73 , and R 74  are independently hydrogen, halogen, C 1 -C 3  alkyl, or C 1 -C 3  haloalkyl; and  
         Q is any one group of Q1 to Q13, Q16, and Q18 to Q23 of the general formula:  
         
           
             
             
                 
                 
             
           
           
             
             
                 
                 
             
           
         
         wherein: 
 in Q1, E 1  and E 2  are independently C 1 -C 6  alkyl optionally substituted with halogen, or C 3 -C 6  cycloalkyl optionally substituted with halogen; or E 1  and E 2  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen;  
 in Q2, E 3  and E 4  are independently C 1 -C 6  alkyl optionally substituted with halogen, or C 3 -C 6  cycloalkyl optionally substituted with halogen; or E 3  and E 4  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen; D 1  and D 2  are independently oxygen or sulfur; and Z 1  is nitrogen or CH;  
 in Q3, E 5  is hydrogen or C 1 -C 6  alkyl optionally substituted with halogen; and D 3  is oxygen or sulfur;  
 in Q4, E 6  and E 7  are independently hydrogen, C 1 -C 6  alkyl optionally substituted with halogen, or C 3 -C 6  cycloalkyl optionally substituted with halogen; or E 6  and E 7  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen;  
 in Q5, E 8  and E 9  are independently hydrogen, C 1 -C 6  alkyl optionally substituted with halogen, or C 3 -C 6  cycloalkyl optionally substituted with halogen; or E 8  and E 9  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen;  
 in Q6, E 10  is hydrogen, C 1 -C 6  alkyl optionally substituted with halogen, or C 1 -C 3  alkoxy optionally substituted with halogen; E 11  is hydrogen or C 1 -C 6  alkyl optionally substituted with halogen; or E 10  and E 11  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen; and E 44  is halogen or C 1 -C 3  alkyl;  
 in Q7, E 12  is C 1 -C 6  alkyl optionally substituted with halogen; and D 4  is oxygen or sulfur;  
 in Q8, E 13  is C 1 -C 6  alkyl optionally substituted with halogen; and E 14  is hydrogen or halogen;  
 in Q9, E 15  is hydrogen or C 1 -C 6  alkyl; E 16  is C 1 -C 6  alkyl optionally substituted with halogen; or E 15  and E 16  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen;  
 in Q10, E 17 , E 18 , and E 19  are independently hydrogen or C 1 -C 6  alkyl; and D 5  is oxygen or sulfur;  
 in Q11, E 20  and E 21  are independently hydrogen or C 1 -C 6  alkyl; and D 6  is oxygen or sulfur;  
 in Q12, E 22  and E 23  are independently hydrogen or C 1 -C 6  alkyl;  
 in Q13, E 24  is hydrogen or C 1 -C 3  alkyl;  
 in Q16, E 30  is C 1 -C 3  alkyl optionally substituted with halogen, E 31  is hydrogen or C 1 -C 3  alkyl optionally substituted with halogen; or E 30  and E 31  may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO 2 , or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen; and E 42  is hydrogen or C 1 -C 3  alkyl optionally substituted with halogen;  
 in Q18, E 34  is C 1 -C 3  alkyl optionally substituted with halogen.  
 
       
     
     
         2 . The condensed heterocyclic compound according to  claim 1 , wherein Q is any one of groups Q1 to Q12.  
     
     
         3 . The condensed heterocyclic compound according to  claim 1 , wherein Q is Q1, of which E 1  and E 2  are combined at their ends to form C 2 -C 5  alkylene (which alkylene may optionally be substituted with methyl or halogen) or C 2 -C 5  alkenylene (which alkenylene may optionally be substituted with methyl or halogen); or 
 Q is Q2, of which E 3  and E 4  are combined at their ends to form C 2 -C 5  alkylene (which alkylene may optionally be substituted with methyl or halogen) or C 2 -C 5  alkenylene (which alkenylene may optionally be substituted with methyl or halogen), and D 1  and Z 1  are as defined above; or    Q is Q4, of which E 6  is C 1 -C 6  alkyl optionally substituted with halogen and E 7  is C 1 -C 6  alkyl optionally substituted with halogen; or    Q is Q4, of which E 6  and E 7  are combined at their ends to form C 2 -C 5  alkylene (which alkylene may optionally be substituted with methyl or halogen) or C 2 -C 5  alkenylene (which alkenylene may optionally be substituted with methyl or halogen); or    Q is Q6, of which E 44  is chlorine or bromine, E 10  is C 1 -C 6  alkyl optionally substituted with halogen, and E 11  is C 1 -C 6  alkyl optionally substituted with halogen; or    Q is Q6, of which E 44  is chlorine or bromine, and E 10  and E 11  are combined at their ends to form C 2 -C 5  alkylene (which alkylene may optionally be substituted with methyl or halogen) or C 2 -C 5  alkenylene (which alkylene may optionally be substituted with methyl or halogen).    
     
     
         4 . The condensed heterocyclic compound according to  claim 1 , wherein Q is selected from the group consisting of Q13, Q16, Q17 and Q18.  
     
     
         5 . The condensed heterocyclic compound according to  claim 1 , wherein Q is Q16 or Q18.  
     
     
         6 . The condensed heterocyclic compound according to  claim 1 , wherein Q is Q16, wherein E 30  is C 1 -C 3  alkyl optionally substituted with halogen, E 31  is hydrogen or C 1 -C 3  alkyl, and E 42  is hydrogen or C 1 -C 3  alkyl; or 
 Q is Q1 8, wherein E 34  is C 1 -C 3  alkyl optionally substituted with halogen; or    Q is Q19, wherein V1 is -CH2- or -CH2-CH2-, and D9 is oxygen; or    Q is Q20, wherein E 35  is C 1 -C 3  alkyl optionally substituted with halogen, Z 2  is nitrogen, and V2 is —CH 2 —CH 2 — or —CH═CH—.    
     
     
         7 . The condensed heterocyclic compound according to any one of  claims 1  to  6 , wherein R 1  is hydrogen or halogen.  
     
     
         8 . The condensed heterocyclic compound according to any one of  claims 1  to  6 , wherein R 2  is hydrogen, halogen, C 1 -C 11  alkyl, nitro, cyano, 
 —N(R 9 )R 10 , —OR 11 , —SR 2 , COOR 4 , —CON(R 15 )R 16 , —COR 17 , —C(R 26 )═NOR 19 —C(R 27 )═C(R 21 )R 22 , or —CH(R 23 )—R 25 .  
 
     
     
         9 . The condensed heterocyclic compound according to any one of  claims 1  to  6 , wherein R 3  is hydrogen, halogen, or nitro.  
     
     
         10 . The condensed heterocyclic compound according to any one of  claims 1  to  6 , wherein R 4  is hydrogen or halogen.  
     
     
         11 . A herbicidal composition comprising the condensed heterocyclic compound according to any one of  claims 1  to  6 , and an inert carrier or diluent.  
     
     
         12 . A method for controlling weeds, which comprises applying an effective amount of the condensed heterocyclic compound according to any one of  claims 1  to  6 , to weeds or to a place where weeds are growing or will grow.