Fused-benzene derivatives useful as herbicides

Abstract

A compound of the formula or its salt represented by the formula (Ia) or Ib) in which variables other than Q are described in the patent application and Q is selected from in which the variables in Q 1 -Q 19 are described in the patent application, provided when Q is Q 1 , Q 3 , Q 4 , Q 13 , Q 18 or Q 19 , structure (Ib) is excluded; when Q is Q 7 , U is CR 9 , nitrogen, NR 2 , C(═O), C(═S) or C(═NR 2 ); herbicidal compositions of said compounds, herbicidal processes using said compounds, defoliant processes using said compounds, and processes for preparing said compounds.

What is claimed is:  
     
         1 . A compound of the formula or its salt represented by the formula (Ia) or (Ib).  
       
         
           
           
               
               
           
         
       
       in which 
 X, Y are independent of each other and are represented by hydrogen, halogen, cyano, nitro, (C 1-4 )alkyl, (C 1-4 )alkoxy, (C 1-4 )haloalkyl or (C 1-4 )haloalkoxy;  
 A is oxygen, nitrogen, NR 1 , CR 3 , CR 3 R 4 ,S(O) n *, C(═O), C(═S) or C(═NR 1 );  
 D is nitrogen or NR 2 ;  
 M is CR 5 , CR 5 R 6 , nitrogen, NR 2 , S(O) n *., C(═O), C(═S) or C(═NR 2 );  
 When A is oxygen, M is nitrogen, NR 2 , S(O) n *, C(═O), C(═S) or C(═NR 2 );  
 E and L are independent of each other and may be selected from CR 7 , CR 8 , CR 7 R 8 , oxygen, nitrogen, NR 7 , S(O) n *, C(═O), C(═S), C(═NR 7 ) or CNR 7 R 8 ;  
 U is CR 9 , oxygen, nitrogen, NR 2 , S(O) n *, C(═O), C(═S) or C(═NR 2 );  
 When U is CR 9 , E is nitrogen;  
 R 1  and R 2  are independent of each other and may be selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynyl, (C 1-6 )alkylcarbonyl, (C 6 )cycloalkylcarbonyl, (C 1-6 )haloalkylcarbonyl, (C 1-6 )alkoxycarbonyl, arylcarbonyl and heteroarylcarbonyl;  
 where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl; R 3 , R 4 , R 5 , R 6 , R 7 , R 8  and R 9  are independent of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, nitro, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkoxy,(C 1-6 )haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )alkynyl, (C 2-6 )alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, (C 3-6 )cyclocarbonyl, carboxy, (C 1-6 )alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxycarbonyl, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 )haloalkoxythiocarbonyl,(C 1-6 )alkylamino, arylsulfonylamino, arylamino, (C 1-6 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 )alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be optionally substituted with one or one more of the following group consisting of halogen, hydroxy, mercapto, cyano, nitro, amino, caboxy, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, haloaryl, alkoxyaryl, aryoxy, arylthio, haloaryloxy, heteroaryl, heteroaryloxy and (C 3-7 )cycloalkyl;  
 n* is represent an integer from 0 to 2;  
 Q is selected from;  
                                                         
 wherein  
 A 1 , and A 2  are independently oxygen or sulfur;  
 R 10  is hydrogen, halogen, cyano, nitro, formyl, (C 1-4 )alkyl, (C 1-4 )haloalkyl, amino, (C 1-4 )alkylamino, (C 1-4 )haloalkylamino, (C 1-4 )alkoxyamino, (C 1-4 )haloalkoxyamino, (C 1-4 )alkylcarbonyl, (C 1-4 )haloalkylcarbonyl, (C 1-4 )haloalkoxycarbonyl, (C 1-4 )alkylcabonylamino, (C 1-4 )haloalkylcarbonylarmino, (C 1-4 )alkoxycarbonylamino, (C 1-4 )haloalkoxycarbonylamino, (C 1-6 )alkoxyalkyl, (C 1-6 )haloalkoxyalkyl, (C 1-6 ) alkylthio, (C 1-6 )haloalkylthio, (C 2-6 )alkenyl, (C 2-6 )haloalkenyl, (C 2-6 )alkynyl or (C 2-6 )haloalkynyl;  
 R 11 , R 12  and R 18  are independent of each other and may be selected from the group consisting of hydrogen, halogen, cyano, (C 1-4 )alkyl, (C 1-4 )haloalkyl, (C 1-4 )alkoxy, (C 1-4 )haloalkoxy, (C 2-6 )alkenyl, (C 2-6 )- 6 )haloalkenyl, hydroxy or amino which may be optionally substituted with (C 1-4 )alkyl and (C 1-4 )haloalkyl;  
 R 13  and R 14  are independent of each other and may be selected from the group consisting of hydrogen, halogen, (C 1-3 )alkyl, (C 1-3 )haloalkyl, hydroxy, (C 1-3 )alkoxy, (C 1-3 )haloalkoxy, cyano, nitro, amino or (C 1-6 )alkylamino;  
 When R 13  and R 14  are taken together with the atoms to which they are attached, they represent a three to seven membered substituted or unsubstituted ring optionally containing oxygen, S(O) n *** or nitrogen with following optional substitutions, one to three halogen, cyano, nitro, hydroxy, amino, carbonyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl or (C 3-7 )cycloalkyl;  
 G is nitrogen or CR 16 ;  
 G′ is NR 15 , oxygen, S(O) n *** or CR 16 R 17 ;  
 G″ is nitrogen, CR 16 , NR 15 , oxygen, S(O) n *** or CR 16 R 17 ;  
 R 15  may be selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )haloalkylcarbonyl, arylcarbonyl and heteroarylcarbonyl; where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 ))alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 R 16  and R 17  are independent of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 ))alkoxy,(C 1-6 ))haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )alkynyl ,(C 2-6 )alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, (C 3-6 )cyclocarbonyl, carboxy, (C 1-6 ))alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 ))haloalkylcarbonyloxy, (C 1-6 ))alkoxycarbonyl, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 )haloalkoxythiocarbonyl,(C 1-6 )alkylamino, arylsulfonylamino, arylamino, (C 1-3 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )-6)alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 )alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be optionally substituted with one or one more of the following group consisting of halogen, hydroxy, mercapto, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 ))haloalkyl, (C 1-6 ))alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 ))alkylaminocarbonyl, (C 1-6 ))haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 n and m are independent of each other and represent an integer from 0 to 2; provided that m+n is 2, 3 or 4;  
 n** is 0 or 1;  
 n*** is represent an integer from 0 to 2;  
 When Q is Q 1 , Q 3 , Q 4 , Q 13 , Q 18  or Q 19 , structure (Ib) is excluded;  
 When Q is Q 7 , U is CR 9 , nitrogen, NR 2 , C(═O), C(═S) or C(═NR 2 );  
 
     
     
         2 . A compound according to the  claim 1  in which 
 X, Y are independent of each other and are represented by hydrogen, halogen or cyano;  
 A is oxygen, nitrogen, NR 1 ;  
 D is nitrogen or NR 2 ;  
 M is nitrogen or NR 2 ;  
 E and L are independent of each other and may be selected from CR 7 , CR 8 , CR 7 R 8 , oxygen, nitrogen, S(O) n *, C(═O), C(═S), C(═NR 7 ) or CNR 7 R 8 ;  
 U is oxygen, nitrogen, NR 2  or S(O) n *;  
 R 1  and R 2  are independently of each other and may be selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynyl, (C 1-6 )alkylcarbonyl, (C 1-6 )cycloalkylcarbonyl, (C 1-6 )haloalkylcarbonyl, arylcarbonyl and heteroarylcarbonyl;  
 where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, mercapto, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 ))alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, haloaryl,alkoxyaryl,heteroaryl and (C 3-7 )cycloalkyl;  
 R 3 , R 4 , R 5 , R 6 , R 7 , R 8  and R 9  are independent of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkoxy,(C 1-6 )haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )alkynyl, (C 2-6 )alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, carboxy, (C 1-6 )alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxycarbonyl, (C 1-6 haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 )haloalkoxythiocarbonyl,(C 1-6 )alkylamino, arylsulfonylamino, arylamino, (C 1-3 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 )alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be non-substituted or substituted with any of the functional groups represented by one more of the following; halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 ))haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 ))haloalkylsulfonyl, aryl, aryloxy, heteroaryl heteroaryloxy and (C 3-7 )cycloalkyl;  
 n* is represent an integer from 0 to 2;  
 When Q is Q 1  or Q 3 , structure (Ib) is excluded;  
 When Q is Q 7 , U is nitrogen or NR 2 ;  
 Q is selected from Q 1 , Q 2 , Q 3 , Q 7 , Q 9 , Q 10 , Q 16  or Q 17 ;  
 wherein  
 A 1  and A 2  are independently oxygen or sulfur;  
 R 10  is (C 1-3 )alkyl, (C 1-3 )haloalkyl or amino  
 R 11  and R 12  are independent of each other and may be selected from the group consisting of hydrogen, halogen, cyano, (C 1-4 )alkyl, (C 1-4 )haloalkyl, (C 1-4 )alkoxy, (C 1-4 )haloalkoxy, (C 2-6 )alkenyl, (C 2-6 )haloalkenyl, hydroxy and amino, which may be optionally substituted with (C 1-4 )alkyl or (C 1-4 )haloalkyl;  
 R 13  and R 14  are independently of each other and may be selected from the group consisting of hydrogen, halogen, (C 1-3 )alkyl, (C 1-3 )haloalkyl, hydroxy, (C 1-3 )alkoxy,  
 (C 1-3 )haloalkoxy, cyano, nitro, amino and (C 1-6 )alkylamino;  
 G is nitrogen or CR 16 ;  
 G′ is NR 15 , oxygen, S(O) n *** or CR 16 R 17 ;  
 R 15  may be selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )alkylcarbonyl, (C 1-6 ))haloalkylcarbonyl, arylcarbonyl and heteroarylcarbonyl;  
 R 16  and R 17  are independent of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkoxy,(C 1-6 )haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )alklynyl ,(C 2-6 alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, carboxy, (C 1-6 )alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxycarbonyl, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 )haloalkoxythiocarbonyl, C 1-6 )alkylamino, arylsulfonylamino, arylamino, (C 1-3 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 )alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be non-substituted or substituted with any of the functional groups represented by one more of the following; halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 ))haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 n and m are independent of each other and represent an integer from 0 to 2; provided that m+n=2 or 3;  
 n** is 0 or 1;  
 n*** is represent an integer from 0 to 2;  
 
     
     
         3 . A compound according to the  claim 2  in which 
 X,Y are independent of each other, represent hydrogen, halogen, cyano;  
 A and U are oxygen;  
 D and M are nitrogen or NR 2 ;  
 E and L are independent of each other and may be CR 7 , CR 8 , CR 7 R 8 , C(═O), C(═S), C(═NR 7 ) or CNR 7 R 8 ;  
 R 2  may be selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )cycloalkylcarbonyl, (C 1-6 )haloalkylcarbonyl, arylcarbonyl and heteroarylcarbonyl;  
 R 7 , and R 8  and are independently of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, cyano, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkoxy,(C 1-6 ))haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )alkynyl,(C 2-6 )alkenyl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, (C 1-6 )alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxycarbonyl, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 ))haloalkoxythiocarbonyl,(C 1-6 )alkylamino, (C 1-3 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )- 6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 ))alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be non-substituted or substituted with any of the functional groups represented by one more of the following ; halogen, hydroxy, cyano, nitro,carboxy (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 ))haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 A 1  and A 2  are oxygen;  
 When Q is Q 1 , Q 7  structure (Ib) is excluded;  
 Q is Q 1 , Q 7  or Q 17 ;  
 R 10  is methyl or amino;  
 R 11  is (C 1-3 )alkyl, (C 1-3 )haloalkyl, (C 1-3 )alkoxy or (C 1-3 )haloalkoxy;  
 R 12  is hydrogen, halogen or (C 1-3 )alkyl;  
 
     
     
         4 . A compound or its salt represented by the formula a, b, c, d, e or f:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       in which 
 X is hydrogen or halogen;  
 Y is halogen, cyano, nitro, (C 1-3 )haloalkyl, or (C 1-3 )haloalkoxy;  
 Q is O 1 , Q 2 , Q 3 , Q 7 , Q 9 , Q 10 , Q 16  or Q 17 ;  
 R 19  is hydrogen, (C 1-6 )alkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )haloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl;  
 where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 ))alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 R 20  is selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkoxy,(C 1-6 )haloalkoxy, (C 1-6 )alkoxyalkyl, (C 2-6 )-)alkynyl,(C 2-6 )alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C 3-6 )cycloalkyl, carboxy, (C 1-6 )alkylcarbonyl, arylcarbonyl, (C 1-3 )haloalkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxycarbonyl, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylthiocarbonyl, (C 1-6 )haloalkylthiocarbonyl, (C 1-6 )alkoxythiocarbonyl, (C 1-6 )haloalkoxythiocarbonyl,(C 1-6 )alkylamino, arylsulfonylamino, arylamino, (C 1-3 )alkylthio, arylthio, (C 2-6 )alkenylthio, (C 2-6 )alkynylthio, (C 1-6 )alkylsulfinyl, (C 2-6 )alkenylsulfinyl, (C 2-6 )alkynylsulfinyl, (C 1-6 )alkylsulfonyl, (C 2-6 )alkenylsulfonyl, (C 2-6 )alkynylsulfonyl, arylsulfonyl, where any of these groups may be non-substituted or substituted with any of the functional groups represented by one more of the following ; halogen, hydroxy, cyano, nitro, amino, caboxyl, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkylcarbonyloxy, (C 1-6 )haloalkylcarbonyl, (C 1-6 )haloalkylcarbonyloxy, (C 1-6 )alkoxy, (C 1-6 )alkoxycarbonyl, aminocarbonyl, (C 1-6 )alkylaminocarbonyl, (C 1-6 )haloalkoxy, (C 1-6 )haloalkoxycarbonyl, (C 1-6 )alkylsulfonyl, (C 1-6 )haloalkylsulfonyl, aryl, heteroaryl and (C 3-7 )cycloalkyl;  
 
     
     
         5 . A method for controlling the growth of undesired plant species in plantation crops which comprises applying to the locus of the crop a herbicidally effective amount of a compound or irs salt of formula (Ia) or (Ib) of the  claim 1 .  
     
     
         6 . Herbicidal composition, characterized in that it contains at least one compound according to the  claim 1 .  
     
     
         7 . The herbicidal composition according to the  claim 6  wherein it contains and an auxiliary agent such as the compound of formula (Ia) or (Ib) or its salt with at least one surfactant or an agricultural adjuvant, solid or liquid diluent.  
     
     
         8 . A method for controlling undesired vegetation in a crop field such as corn or soybean by applying to the locus of the crop to be protected a herbicidally effective amount of a compound of the  claim 1 .  
     
     
         9 . A method to defoliate potato and cotton using a compound of the  claim 1 .  
     
     
         10 . A process for the preparation of the compound of formula (Ib) as claimed in  claim 1 , which comprises cyclizing a compound according to formula d  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y and Q are as previously defined, with an acid chloride, acid anhydride or acid in the presence of a cyclization catalyst in an inert solvent or diluent.  
 
     
     
         11 . A process of the preparation of the intermediate of the formula VIII, which comprises reducing a compound according to formula VI  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y and R 7  are as previously defined.  
 
     
     
         12 . A process for the preparation of the intermediate of the formula VI as claimed in  claim 11 , which comprises nitrating a compound according to formula V  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y and R 7  are as previously defined.  
 
     
     
         13 . A process for the preparation of the intermediate of the formula V as claimed in  claim 12 , which comprises cyclizing a compound according to formula IV  
       
         
           
           
               
               
           
         
       
       wherein 
 X and Y are as previously defined, with an acid or acid chloride in the presence of a catalyst in an inert solvent or diluent.  
 
     
     
         14 . A process for the preparation of the intermediate of the formula IV as claimed in  claim 13 , which comprises reducing a compound according to formula III  
       
         
           
           
               
               
           
         
       
       wherein 
 X and Y are as previously defined, with a reducing reagent.  
 
     
     
         15 . A process for the preparation of the intermediate of the formula VIII as claimed in  claim 11 , which comprises deprotecting a compound according to formula XVIII  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y and R 7  are as previously defined.  
 
     
     
         16 . A process for the preparation of the compound of the formula XXV as claimed in  claim 1 , which comprises cyclizing a compound according to formula XXIV  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y, R 7 , R 8 , R 10 , R 11  and R 12  are as previously defined.  
 
     
     
         17 . A process for the preparation of the compound of the formula XXVI as claimed in  claim 1 , which comprises cyclizing a compound according to formula XXIV  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y, R 7 , R 8 , R 10 , R 11  and R 12  are as previously defined.  
 
     
     
         18 . A process of the preparation of the compound of the formula XXVII as claimed in  claim 1 , which comprises cyclizing a compound according to formula XXIV  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y, R 7 , R 10 , R 11  and R 12  are as previously defined.  
 
     
     
         19 . A process for the preparation of the compound of the formula XXVIII as claimed in  claim 1 , which comprises a cyclizing a compound according to formula XXIV.  
       
         
           
           
               
               
           
         
       
       wherein 
 X, Y, R 7 , R 8 , R 10 , R 11  and R 12  are as previously defined.  
                         U.S. PATENT DOCUMENTS                                       4,859,229   July 1987   J. Wenger et al.         5,169,431   September 1991   M. Enomoto et al.         5,346,881   August 1993   G. Teodooridis         5,521,147   February 1995   G. Teodooridis                                                      
                         FOREIGN PATENT DOCUMENTS                                       0271170   June 1988   European         93/14073   December 1992   WIPO         95/53746   June 1995   WIPO         9301973   May 1996   Japan         97/08170   August 1996   WIPO         97/08171   August 1996   WIPO         97/12886   October 1996   WIPO         97/29105   February 1997   WIPO         97/42188   May 1997   WIPO         98/27090   June 1998   WIPO         98/38188   September 1998   WIPO         99/06394   February 1999   WIPO         99/31091   June 1999   WIPO