1 - (3-heterocyclylphenyl) isothiourea, -isourea, -guanidine and -amidine herbicidal agents

Abstract

There are provided 1-(3-heterocyclyphenyl)isothiourea, -isourea, -guanidine and -amidine compounds of formula I Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.

What is claimed is:  
     
         1 . A compound having the structural formula I  
       
         
           
           
               
               
           
         
       
       wherein 
 X and Y are each independently hydrogen, halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or S(O) m R 1 ;  
 R is hydrogen, 
 a C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 8 alkenyl, C 5 -C 7 -cycloalkenyl or C 3 -C 8 alkynyl group, wherein each group is optionally substituted with any combination of one to six halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(W)R 2  groups, one or two C(W)OR 3  groups, one or two C(W)NR 4 R 5  groups, one or two P(V) (OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups, one or two OC(W)R 11  groups, one or two NR 12 S(O) n R 13  groups, one or two C(W)NR 12 S(O) n R 13  groups, 
 one 4- to 10-membered heterocyclic ring option-ally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 -alkoxyalkyl groups, one or two C 2 -C 6 halo-alkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6 alkylcarbonyalkyl groups, one to three C 3 -C 6 haloalkyl-carbonylalkyl groups, one or two NR 15 S(O) p R 16  groups or one or two C(W)NR 15 S(O) p R 16  groups, or  
 one phenyl group optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups,-one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6−  haloalkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6 alkylcarbonyl-alkyl groups, one to three C 3 -C 6 haloalkyl-carbonylalkyl groups one or two NR 15 S(O) p R 16  groups or one or two C(W)NR 15 S(O) p R 16  groups,  
 
 
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 -alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 -alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxy-alkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxy-carbonylalkyl groups, one to three C 3 -C 6 halo-alkoxycarbonylalkyl groups, one to three C 3 -C 6 -alkylcarbonylalkyl groups, one to three C 3 -C 6 -haloalkylcarbonylalkyl groups, one or two NR 15 S(O) p R 16  groups or one or two C(W)NR 15 S(O) p R 16  groups,  
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 -haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6 alkylcarbonylalkyl groups, one to three C 3 -C 6 haloalkylcarbonylalkyl groups, one or two NR 15 S(O) p R 16  groups or one or two C(W)NR 15 S(O) p R 16  groups,  
 OR 17 ,NR 18 R 19 ,NR 20 S(O) q R 21 ,NR 22 C(V)R 23 ,NR 24 P(V)(OR 25 ) 2 , C(V)NR 20 S(O) q R 21 ,cyano,S(O) q R 26 ,P(V)(OR 27 ) 2 ,C (V) R 28  or C(V) OR 29 ;  
 W is O, S, NR 30 , NOR 31  or NNR 32 R 33 ;  
 V and Z are each independently O or S;  
 R 1  and R 14  are each independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;  
 R 2  is hydrogen, C 2 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 -alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkoxy-carbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6−  alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxy-alkyl groups, one or two nitro groups, one or two cyano groups, one NR 15 S(O) p R 16  group, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 haloalkoxy-carbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 haloalkylcarbonyl group, one C 3 -C 6−  alkoxycarbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group or one C 3 -C 6 haloalkylcarbonylalkyl group,  
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxy-alkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one NR 15 S(O) p R 16  group, one C 2 -C 6 -alkoxycarbonyl group, one C 2 -C 6 haloalkoxy-carbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 haloalkylcarbonyl group, one C 3 -C 6 -alkoxycarbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group or one C 3 -C 6 haloalkylcarbonylalkyl group,  
 C 1 -C 4 alkyl substituted with one phenyl group wherein the phenyl group is optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 -alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 C 1 -C 4 alkyl substituted with one 4- to 10-membered heterocyclic ring wherein the heterocyclic ring is optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkenyl C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, 
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;  
 
 R 4  and R 5  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, hydroxy, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 haloalkoxycarbonylalkyl, C 2 -C 6 hydroxy-carbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 halo-alkylsulfonylalkyl, S(O) p R 16 , 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 halo-alkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 provided that only one of R 4  and R 5  can be hydroxy or C 1 -C 6 alkoxy, and  
 when R 4  and R 5  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 R 6 , R 25  and R 27  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 7 , R 8  and R 17  are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkylcarbonylalkyl, C 2 -C 6 haloalkylcarbonylalkyl, C 2 -C 6 alkoxycarbonylalkyl, C 2 -C 6 haloalkoxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, C(V)NR 12 S(O) n R 13 , 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 halo-alkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 9 , R 10 , R 18 , R 19 , R 32  and R 33  are each independently hydrogen, C 1 -C 4 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 halo-alkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 -haloalkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4  haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 9  and R 10  or R 18  and R 19  or R 32  and R 33  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 R 1 , is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxy-alkyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 haloalkyl-carbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 halo-alkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4  haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 12 , R 15 , R 20  and R 24  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;  
 R 13 , R 21 , R 22 , R 23 , R 26 , R 28  and R 29  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 -haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 haloalkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 halo-alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one C 3 -C 6 alkoxy-carbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group, one C 3 -C 6 haloalkylcarbonylalkyl group or one C 2 -C 6 hydroxycarbonylalkyl group,  
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6− alkoxyalkyl groups, one or two C 2 -C 6 halo-alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one C 3 -C 6 alkoxy-carbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group, one C 3 -C 6 haloalkylcarbonylalkyl group or one C 2 -C 6 hydroxycarbonylalkyl group,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 16  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 -haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 haloalkoxycarbonylalkyl, 
 phenyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 halo-alkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 30  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one C 2 -C 6 alkoxy-alkyl group, one C 2 -C 6 haloalkoxyalkyl group, one NR 15 S(O) n R 16  group, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 -alkoxycarbonylalkyl group, one C 3 -C 6 alkyl-carbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group or one C 3 -C 6 haloalkyl-carbonylalkyl group,  
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one C 2 -C 6 alkoxyalkyl group, one C 2 -C 6 haloalkoxyalkyl group, one NR 15 S(O) n R 16  group, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 -alkoxycarbonylalkyl group, one C 3 -C 6 alkyl-carbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group or one C 3 -C 6 haloalkyl-carbonylalkyl group,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 , haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 31  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 -haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 2 -C 6 haloalkoxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, C 2 -C 6 hydroxy-carbonylalkyl, C(V)NR 12 S(O) n R 13 , 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 A is —O—, —S(O) r —, —NR 34 — or —CR 35 R 36 —;  
 B is —CR 37 R 38 (CR 39 R 40 ) s —, —C (═T)— or —C(═CR 41 R 42 )—;  
 R 34 , R 35 , R 36 , R 37 , R 38 , R 39  and R 40  are each independently hydrogen, halogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(W)R 2  groups, one or two C(W)OR 3  groups, one or two C(W)NR 4 R 5  groups, one or two P(V)(OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups or one or two OC(W)R 21   −  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 6 alkenyl,  
 C 3 -C 6 haloalkenyl  
 C 3 -C 6 alkynyl,  
 C 3 -C 6 haloalkynyl,  
 C(V)NR 12 S(O) n R 13 ,  
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 halo-alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one NR 15 S(O) p R 16  group, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 halo-alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 haloalkylcarbonyl group, one C 3 -C 6  alkoxycarbonylalkyl group, one C 3 -C 6 halo-alkoxycarbonylalkyl group, one C 3 -C 6 alkyl-carbonylalkyl group or one C 3 -C 6 haloalkyl-carbonylalkyl group,  
 a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxy-alkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one NR 15 S(O) p R 16  group, one C 2 -C 6 -alkoxycarbonyl group, one C 2 -C 6 haloalkoxy-carbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 haloalkylcarbonyl group, one C 3 -C 6 -alkoxycarbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group or one C 3 -C 6 haloalkylcarbonylalkyl group,  
 C 1 -C 4 alkyl substituted with one phenyl group wherein the phenyl group is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one C 2 -C 6 alkoxy-carbonyl group, one C 2 -C 6 haloalkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 -haloalkylcarbonyl group, one C 3 -C 6 alkoxy-carbonylalkyl group, one C 3 -C 6 haloalkoxy-carbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group, one C 3 -C 6 haloalkylcarbonylalkyl group, one C 3 -C 8 alkoxycarbonylalkoxy group or one C 2 -C 8 hydroxycarbonylalkoxy group, or  
 C 1 -C 4 alkyl substituted with one 4- to 10-membered heterocyclic ring wherein the heterocyclic ring is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 halo-alkoxyalkyl groups, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 haloalkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 2 -C 6 haloalkylcarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group, one C 3 -C 6 haloalkoxycarbonylalkyl group, one C 3 -C 6 alkylcarbonylalkyl group or one C 3 -C 6 -haloalkylcarbonylalkyl group, and  
 when R 35  and R 36  or R 37  and R 38  or R 39  and R 40  are taken together with the atom to which they are attached, they represent a ring in which R 35 R 36 , or R 37 R 38  or R 39 R 40  is a C 2 -C 6 alkylene group;  
 
 T is O, S, NR 30 , NOR 31  or NNR 32 R 33 ;  
 R 41  and R 42  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, hydroxy-carbonyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 halo-alkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups or one C 3 -C 8 -alkoxycarbonylalkoxy group,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 41  and R 42  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring option-ally interrupted with one group selected from O, S(O) r  or NR 31 , and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 m and r are each independently an integer of 0, 1 or 2;  
 n, p and q are each independently an integer of 1 or 2;  
 s is an integer of 0 or 1;  
 Q is selected from  
                     
 D and D 1  are each independently O or S;  
 E is hydroxy, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio;  
 R 43  and R 44  are each independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyi, C 3 -C 7 acycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, cyano, amino, hydroxy or benzyl, and when R 43  and R 44  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 R 45  and R 46  are each independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 51 , S(O) t R 52  or NR 53 R 54 , and when R 45  and R 46  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 R 47 , R 49  and R 50  are each independently hydrogen, halogen or C 1 -C 6 alkyl;  
 R 48  is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 51  or SR 52 ;  
 R 51  and R 52  are each independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 7 cycloalkyl, C 1 -C 4 cyanoalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, benzyl or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 53  is hydrogen, C 1 -C 4 alkyl, benzyl or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 54  in hydrogen, C 1 -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 7 cyclo-alkyl, benzyl, S(O) t R 52  or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups; and  
 
 t is an integer of 0, 1 or 2; and the agriculturally acceptable salts thereof.  
 
     
     
         2 . The compound according to  claim 1  wherein 
 X is hydrogen or halogen;  
 Y is hydrogen, halogen, nitro or cyano;  
 R is hydrogen, 
 a C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkenyl or C 3 -C 8 alkynyl group, wherein each group is optionally substituted with any combination of one to six halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(O)R 2  groups, one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O)(OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups, one or two OC(O)R 11  groups, one or two NR 12 S(O) n R 13  groups, one or two C(O)NR 12 S(O) n R 13  groups, 
 one 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 lalkoxyalkyl groups, one or two C 2 -C 6 -haloalkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6 alkylcarbonyalkyl groups, one to three C 3 -C 6 haloalkyl-carbonylalkyl groups, one or two NR 15 S(O) p R 16  groups or one or two C(O)NR 15 S(O) p R 16  groups, or  
 one phenyl group optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6−  alkylcarbonylalkyl groups, one to three C 3 -C 6 haloalkylcarbonylalkyl groups, one or two NR 15 S(O) p R 16  groups or one or two C(O)NR 15 S(O) p R 16  groups,  
 
 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 -haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 2 -C 6 haloalkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups, one to three C 3 -C 6 haloalkoxycarbonylalkyl groups, one to three C 3 -C 6 alkylcarbonylalkyl groups, one to three C 3 -C 6 haloalkylcarbonylalkyl groups or one or two NR 15 S(O) p R 1 , groups,  
 OR 17 ,  
 NR 18 R 19 ,  
 NR 20 S(O) q R 21 ,  
 NR 22 C(O)R 23 ,  
 C(O)NR 20 S (O) q R 21 ,  
 S(O) q R 26 ,  
 C(O)R 28  or  
 C(O)OR 29 ;  
 Z is O;  
 R 14  is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;  
 R 2  is hydrogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one C 2 -C 6 alkoxycarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group or one C 3 -C 6 haloalkoxycarbonylalkyl group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;  
 
 R 4  and R 5  are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, hydroxy, C 3 -C 6 alkenyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, S(O) p R 16 , 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 provided that only one of R 4  and R 5  can be hydroxy or C 1 -C 6 alkoxy, and  
 when R 4  and R 5  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 R 6  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 7  and R 8  are each independently hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 alkoxycarbonylalkyl or C 2 -C 6 hydroxy-carbonylalkyl;  
 R 17  is hydrogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkylcarbonylalkyl, C 2 -C 6 haloalkylcarbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 9  and R 10  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonylalkyl, C 1 -C 6 alkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 9  and R 10  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 R 10  and R 19  are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 al koxycarbonylalkyl, C 3 -C 6 haloalkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 halo-alkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 18  and R 19  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 R 11  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 12 , R 15  and R 20  are each independently hydrogen or C 1 -C 6 alkyl;  
 R 13 , R 16 , R 21  and R 26  are each independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, or 
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 22  is hydrogen or C 1 -C 6 alkyl;  
 R 23  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cyclo-alkyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 haloalkyl-carbonylalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 3 -C 6 halo-alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4−  haloalkoxy groups;  
 
 R 28  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 alkoxy-carbonylalkyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 29  is hydrogen, C 1 -C 6 alkyl or benzyl;  
 A is —O—, —S(O) r —, or —NR 34 —;  
 B is —CR 37 R 38 —, —C(O)— or —C(═CR 41 R 42 )—;  
 R 34  is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(O)R 2  groups, one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O)(OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups or one or two OC(O)R 11  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 6 alkenyl,  
 C 3 -C 6 alkynyl,  
 C(O)NR 12 S(O) n R 13 ,  
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6− alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6− alkoxycarbonylalkyl group or one C 3 -C 6 alkyl-carbonylalkyl group, or  
 C 1 -C 4 alkyl substituted with one phenyl group wherein the phenyl group is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6− alkoxyalkyl groups, groups, one C 2 -C 6 alkoxy-carbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group or one C 3 -C 6 -alkylcarbonylalkyl group;  
 
 R 37  and R 38  are each independently hydrogen, halogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(O)R 2  groups, one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O)(OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups or one or two OC(O)R 11  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 6 alkenyl,  
 C 3 -C 6 haloalkenyl  
 C 3 -C 6 alkynyl,  
 C 3 -C 6 haloalkynyl,  
 C(O)NR 12 S(O) n R 13 ,  
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one C 2 -C 6− alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group or one C 3 -C 6 alkylcarbonylalkyl group, or  
 C 1 -C 4 alkyl substituted with one phenyl group wherein the phenyl group is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one C 2 -C 6 alkoxy-carbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group or one C 3 -C 6 -alkylcarbonylalkyl group, and  
 when R 37  and R 38  are taken together with the atom to which they are attached, they represent a ring in which R 37 R 38  is a C 2 -C 6 alkylene group;  
 
 R 41  and R 42  are each independently hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, hydroxy-carbonyl, C 3 -C 6 alkylcarbonylalkyl, C 3 -C 6 alkoxy-carbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups,  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 furfural optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 41  and R 42  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted with one group selected from O, S(O) r  or NR 31 , and optionally substituted with one to three methyl groups or one or more halogen atoms;  
 
 r is an integer of 0, 1 or 2;  
 n, p and q are each independently an integer of 1 or 2;  
 Q is selected from  
                     
 D and D 1  are each independently O or S;  
 R 43  and R 44  are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, amino, or benzyl;  
 R 45  and R 46  are each independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl or C 3 -C 6 alkynyl, and when R 45  and R 46  are taken together with the atom to which they are attached, they represent a three- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms; and  
 R 47  and R 48  are each independently hydrogen, halogen or C 1 -C 6 alkyl.  
 
     
     
         3 . The compound according to  claim 2  wherein 
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 8 alkyl optionally substituted with any combination of one to six halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(O)R 2  groups, one or two C(O) OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O)(OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups, one or two C(O)NR 12 S(O) n R 13  groups, 
 one furyl group optionally substituted with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C(O)OR 14  groups or one or two C(O)R 14  groups,  
 one pyridyl group optionally substituted with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C(O)OR 14  groups or one or two C(O)R 14  groups, or  
 one phenyl group optionally substituted with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C(O)OR 14  groups or one or two C(O)R 14  groups,  
 
 
 phenyl optionally substituted with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C(O)OR 14  groups, one or two C(O)R 14  groups, one to three C 3 -C 6 alkoxycarbonylalkyl groups or one or two NR 15 S(O) p R 16  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 8 alkenyl,  
 C 3 -C 8 alkynyl,  
 OR 17 ,  
 NR 18 R 19 ,  
 C(O)R 28  or  
 C(O)QOR 29 ;  
 Z is O;  
 R 14  is C 1 -C 4 alkyl;  
 R 2  is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkoxyalkyl or C 3 -C 6 -alkoxycarbonylalkyl;  
 R 3  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 -haloalkoxy groups;  
 
 R 4  and R 5  are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 halo-alkoxy groups, and  
 when R 4  and R 5  are taken together with the atom to which they are attached, they represent a ring in which R 4 R 5  is a C 2 -C 6 alkylene group;  
 
 R 6  is hydrogen, C 1 -C 6 alkyl or benzyl;  
 R 7  and R 8  are each independently hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 alkoxycarbonylalkyl or C 2 -C 6 hydroxy-carbonylalkyl;  
 R 17  is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 alkoxycarbonylalkyl, C 2 -C 6 -hydroxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 9  and R 10  are each independently hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonylalkyl, and 
 when R 9  and R 10  are taken together with the atom to which they are attached, they represent a ring in which R 9 R 10  is a C 2 -C 6 alkylene group;  
 
 R 18  and R 19  are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkoxycarbonylalkyl, C 2 -C 6 hydroxycarbonylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 haloalkylsulfonylalkyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, and  
 when R 18  and R 19  are taken together with the atom to which they are attached, they represent a ring in which R 18 R 19  is a C 2 -C 6 alkylene group;  
 
 R 12  and R 15  are each independently hydrogen or C 1 -C 6 alkyl;  
 R 13  and R 16  are each independently C 1 -C 6 alkyl, C 1 -C 6 halo-alkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, or 
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 -alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 28  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl C 3 -C 6 alkynyl, C 3 -C 6 alkoxycarbonylalkyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 29  is hydrogen, C 1 -C 6 alkyl or benzyl;  
 A is —O—, —S(O) r —, or —NR 34 —;  
 B is —CR 37 R 38 — or —C(═CR 41 R 42 )—;  
 R 34  is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one or two C(O)OR 3  groups or one or two C(O) NR 4 R 5  groups,  
 C 3 -C 6 alkenyl,  
 C 3 -C 6 alkynyl,  
 phenyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 -alkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6 alkylcarbonyl group, one C 3 -C 6 -alkoxycarbonylalkyl group or one C 3 -C 6 alkyl-carbonylalkyl group, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 R 37  and R 38  are each independently hydrogen, halogen, 
 C 1 -C 6  alkyl optionally substituted with one or two cyano groups, one or two C(O)R 2  groups, one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O)(OR 6 ) 2  groups, one or two OR 7  groups or one or two NR 9 R 10  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 6 alkenyl,  
 C 3 -C 6 alkynyl,  
 C(O)NR 12 S(O) n R 13 , or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one C 2 -C 6 alkoxycarbonyl group, one C 2 -C 6  alkylcarbonyl group, one C 3 -C 6 alkoxycarbonylalkyl group or one C 3 -C 6  alkylcarbonylalkyl group, and  
 when R 37  and R 38  are taken together with the atom to which they are attached, they represent a ring in which R 37 R 38  is a C 2 -C 6 alkylene group;  
 
 R 41  and R 42  are each independently hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, hydroxy-carbonyl, or 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 r is an integer of 0, 1 or 2;  
 n and p are each independently an integer of 2; and  
 Q is selected from  
                     
 
     
     
         4 . The compound according to  claim 3  wherein 
 X is fluorine;  
 Y is chlorine;  
 R is C 1 -C 8 alkyl optionally substituted with any combination of one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two P(O) (OR 6 ) 2  groups, one or two OR 7  groups, one or two SR 8  groups, one or two NR 9 R 10  groups, one or two C(O)NR 12 S(O) n R 13  groups, one furyl group or 
 one phenyl group optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups or one nitro group,  
 phenyl optionally substituted with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups, one or two C 2 -C 6 alkoxyalkyl groups, one or two C 3 -C 6 alkoxycarbonylalkyl groups or one or two NR 15 S(O) p R 16  groups,  
 C 3 -C 7 cycloalkyl,  
 C 3 -C 8 alkenyl or  
 C 3 -C 8 alkynyl;  
 
 Z is O;  
 R 3  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 alkoxycarbonylalkyl, 
 phenyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 -haloalkoxy groups;  
 
 R 4  and R 5  are each independently hydrogen or C 1 -C 6 alkyl, and when R 4  and R 5  are taken together with the atom to which they are attached, they represent a ring in which R 4 R 5  is a C 2 -C 6 alkylene group;  
 R 6  is hydrogen or C 1 -C 6 alkyl;  
 R 7  and R 8  are each independently hydrogen, C 1 -C 6 alkyl C 2 -C 6 alkoxycarbonylalkyl or C 2 -C 6 hydroxycarbonylalkyl;  
 R 9  and R 10  are each independently hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonylalkyl, and 
 when R 9  and R 10  are taken together with the atom to which they are attached, they represent a ring in which R 9 R 10  is a C 2 -C 6 alkylene group;  
 
 R 12  and R 15  are hydrogen;  
 R 13  and R 16  are each independently C 1 -C 6 alkyl, C 3 -C 6 -haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6 alkynyl, or 
 benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 -alkoxy groups or one to three C 1 -C 4 haloalkoxy groups;  
 
 A is —O— or —S(O) r —;  
 B is —CR 37 R 38 — or —C(═CR 41 R 42 )—;  
 R 37  and R 38  are each independently hydrogen, halogen, 
 C 1 -C 6 alkyl optionally substituted with one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two OR 7  groups or one or two NR 9 R 10  groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups or one C 3 -C 6 alkoxycarbonylalkyl group, and  
 when R 37  and R 38  are taken together with the atom to which they are attached, they represent a ring in which R 37 R 38  is a C 2 -C 6 alkylene group;  
 
 R 41  and R 42  are each independently hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or hydroxy-carbonyl;  
 r is an integer of 0, 1 or 2;  
 n and p are each independently an integer of 2; and  
 Q is selected from  
                     
 
     
     
         5 . The compound according to  claim 4  selected from the group consisting of 
 N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;  
 3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-thiazoli-dineacetic acid, diethyl ester;  
 ethyl 5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6-acetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl ester;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacetate;  
 α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetic acid, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;  
 ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)methyl]-4-oxo-3-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;  
 methyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 isopropyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;  
 2-fluoroethyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-oxo-3-thiazolidineacetate;  
 allyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;  
 isopropyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 cyclopropylmethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 ethyl 5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinylidene)amino]-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 ethyl 5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 methyl 2-{(2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepropionate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyriziidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, D-;  
 methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-α-(p-nitrobenzyl)-3-thiazolidineacetate, L-;  
 ethyl a-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and  
 methyl α-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-dineacetate, DL-.  
 
     
     
         6 . A method for the control of undesirable plant species which comprises applying to the foliage of said plants or to the soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of a compound having the structural formula I  
       
         
           
           
               
               
           
         
       
       wherein A, B, Q, R, X, Y and Z are as described in  claim 1 .  
     
     
         7 . The method according to  claim 6  wherein A, B, Q, R, X, Y and Z are as described in  claim 2 .  
     
     
         8 . The method according to  claim 7  wherein A, B, Q, R, X, Y and Z are as described in  claim 3 .  
     
     
         9 . The method according to  claim 8  wherein A, B, Q. R, X, Y and Z are as described in  claim 4 .  
     
     
         10 . The method according to  claim 9  wherein the compound is selected from the group consisting of 
 N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazoli-dinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;  
 3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-thiazoli-dineacetic acid, diethyl ester;  
 ethyl 5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6-acetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl ester;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacetate;  
 α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetic acid, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;  
 ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-dineacetate;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)methyl]-4-oxo-3-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-flucromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;  
 methyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 isopropyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;  
 2-fluoroethyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-oxo-3-thiazolidineacetate;  
 allyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;  
 isopropyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 cyclopropylmethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 ethyl 5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinyli-dene)amino]-2-fluorophenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione;  
 3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 ethyl 5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropionate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, D-;  
 methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-α-(p-nitrobenzyl)-3-thiazolidineacetate, L-;  
 ethyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and  
 methyl α-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, DL-.  
 
     
     
         11 . The method according to  claim 6  wherein the compound is applied to the foliage of the undesirable plant species or to the soil or water containing seeds or other propagating organs thereof in the presence of crop plants, crop seeds or other crop propagating organs.  
     
     
         12 . The method according to  claim 11  wherein the crop is a cereal crop.  
     
     
         13 . The method according to  claim 12  wherein the cereal crop is selected from the group consisting of corn, wheat and rice.  
     
     
         14 . The method according to  claim 13  wherein the cereal crop is corn and the compound is selected from the group consisting of 
 N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;  
 ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidine-acetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;  
 isopropyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;  
 2-fluoroethyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate; and  
 2-{(2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester.  
 
     
     
         15 . The method according to  claim 13  wherein the cereal crop is wheat and the compound is selected from the group consisting of 
 3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-thiazoli-dineacetic acid, diethyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;  
 ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidine-acetate;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-[(methylcarbamoyl)methyl]-4-oxo-3-thiazolidineacetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;  
 isopropyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;  
 2-fluoroethyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidine-acetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester;  
 ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(hydroxyethyl)-4-oxo-3-thiazolidineacetate; and  
 cyclopropylmethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate.  
 
     
     
         16 . The method according to  claim 13  wherein the cereal crop is rice and the compound is selected from the group consisting of 
 ethyl 5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;  
 3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;  
 methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropionate;  
 methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;  
 methyl α-benzyl-2-{{2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, D-;  
 methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-α-(p-nitrobenzyl)-3-thiazolidineacetate, L-;  
 ethyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and  
 methyl α-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyri-midinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, DL-.  
 
     
     
         17 . The method according to  claim 11  wherein the crop is soybean.  
     
     
         18 . The method according to  claim 17  wherein the compound is selected from the group consisting of 
 ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidine-acetate;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;  
 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester;  
 allyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate; and  
 3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(tri-fluoromethyl)-2,4(1H,3H)-pyrimidinedione.  
 
     
     
         19 . The method according to  claim 6  wherein the compound is applied to the foliage of the undesirable plant species or to the soil or water containing seeds or other propagating organs thereof at a rate of about 0.01 kg/ha to 1 kg/ha.  
     
     
         20 . The method according to  claim 6  wherein the compound is applied in combination with or in conjunction with one or more other biological compounds.  
     
     
         21 . A herbicidal composition which comprises an inert solid or liquid carrier and a herbicidally effective amount of a compound having the structural formula I  
       
         
           
           
               
               
           
         
       
       wherein A, B, Q, R, X, Y and Z are as described in  claim 1 .  
     
     
         22 . The composition according to  claim 21  wherein A, B, Q, R, X, Y and Z are as described in  claim 2 .  
     
     
         23 . The composition according to  claim 22  wherein A, B, Q, R, X, Y and Z are as described in  claim 3 .  
     
     
         24 . The composition according to  claim 23  wherein A, B, Q, R, X, Y and Z are as described in  claim 4 .  
     
     
         25 . The composition according to claim  24 / wherein the compound is selected from the group consisting of 
 N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;    3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;    ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-thiazoli-dineacetic acid, diethyl ester;    ethyl 5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6-acetate;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl ester;    ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacetate;    α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetic acid, L-;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;    ethyl 5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)methyl]-4-oxo-3-thiazolidineacetate;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;    methyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;    isopropyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;    methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;    2-fluoroethyl 3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;    2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic acid, 3-ethyl ester;    ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-oxo-3-thiazolidine-acetate;    allyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    isopropyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;    cyclopropylmethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    ethyl 5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinyli-dene)amino]-2-fluorophenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione;    3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;    3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;    ethyl 5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;    3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;    methyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepropionate;    methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, D-;    methyl 2-{{2-chloro-5-[3,G-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-α-(p-nitrobenzyl)-3-thiazolidineacetate, L-;    ethyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and    methyl α-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyri-midinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-dineacetate, DL-.    
     
     
         26 . The composition according to  claim 21  which further comprises one or more other biological compounds.  
     
     
         27 . A compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 U is —N═C═NR, —N═C═S or  
                     
 Q is  
                     
 D, D 1 , R, R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , X and Y are as described in  claim 1 .  
 
     
     
         28 . The compound according to  claim 27  wherein 
 U is —N═C═NR, —N═C═S or  
                     
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6  alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR 3  groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 3 alkyl;  
 R 7  is hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonylalkyl; 
 and  
 
 R 8  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonyl.  
 
     
     
         29 . A method for the preparation of a compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR3 groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 6 alkyl;  
 R 7  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonylalkyl; 
 and  
 
 R 8  is hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonyl which method comprises reacting a substituted aniline compound having the structural formula  
                     
 wherein Q. X and Y are as described above with an isothiocyanate compound having the structural formula 
 S═C═N—R 
 wherein R is as described above.  
 
     
     
         30 . The method according to  claim 29  wherein the reaction is conducted in the presence of a solvent.  
     
     
         31 . A method for the preparation of a compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR 3  groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 3 alkyl;  
 R 7  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonylalkyl; 
 and  
 
 R 8  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonyl which method comprises reacting an isothiocyanate compound having the structural formula  
                     
 wherein Q. X and Y are as described above with a primary amine compound having the structural formula 
 H 2 NR 
 wherein R is as described above.  
 
     
     
         32 . The method according to  claim 31  wherein the reaction is conducted in the presence of a solvent.  
     
     
         33 . A method for the preparation of a compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR 3  groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 3 alkyl;  
 R 7  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonylalkyl;  
 R 8  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonyl;  
 R 37  and R 38  are each independently hydrogen, halogen, 
 C 1 -C 6 alkyl optionally substituted with one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two OR 7  groups or one or two NR 9 R 10  groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups or one C 3 -C 6 alkoxycarbonylalkyl group, and  
 when R 37  and R 38  are taken together with the atom to which they are attached, they represent a ring in which R 37 R 38  is a C 2 -C 6 alkylene group;  
 
 R 4  and R 5  are each independently hydrogen or C 1 -C 6 alkyl, and when R 4  and R 5  are taken together with the atom to which they are attached, they represent a ring in which R 4  and R 5  is a C 2 -C 6 alkylene group; and  
 R 9  and R 10  are each independently hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonylalkyl, and when R 9  and R 10  are taken together with the atom to which they are attached, they represent a ring in which R 9 R 10  is a C 2 -C 6 alkylene group  
 which method comprises reacting a substituted thiourea compound having the structural formula  
                     
 wherein Q, R, X and Y are as described above with a ketone compound having the structural formula  
                     
 wherein R 37  and R 38  are as described above, and X 1  is halogen.  
 
     
     
         34 . The method according to  claim 33  wherein the reaction is conducted in the presence of a solvent.  
     
     
         35 . The method according to  claim 33  wherein the reaction is conducted in the presence of a base.  
     
     
         36 . A method for the preparation of a compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR 3  groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 6 alkyl;  
 R 7  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonylalkyl; 
 and  
 
 R 8  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonyl which method comprises reacting a substituted thiourea compound having the structural formula  
                     
 wherein Q, R, X and Y are as described above with a compound having the structural formula 
 R 55 SO 2 Cl 
 wherein R 55  is C 1 -C 4 alkyl or phenyl optionally substituted with one or two C 1 -C 4 alkyl groups in the presence of a base.  
 
     
     
         37 . A method for the preparation of a compound having the structural formula  
       
         
           
           
               
               
           
         
       
       wherein 
 Q is  
                     
 X is hydrogen, fluorine or chlorine;  
 Y is fluorine, chlorine, nitro or cyano;  
 R is hydrogen, 
 C 1 -C 6 alkyl optionally substituted with one to three halogen atoms, one or two C(O)OR 3  groups, one cyano group, one OR 7  group, one SR 8  group, one P(O)(OR 6 ) 2  group, or  
 a C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl, benzyl or furfural group, wherein each group is optionally substituted with one to three halogen atoms, one C 1 -C 3 alkoxy group or one C(O)OR 3  group;  
 
 R 3  is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;  
 R 6  is hydrogen of C 1 -C 3 alkyl;  
 R 7  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonylalkyl;  
 R 8  is hydrogen, C 1 -C 3 alkyl or C 3 -C 6 alkoxycarbonyl;  
 R 37  and R 38  are each independently hydrogen, halogen, 
 C 1 -C 6 alkyl optionally substituted with one or two C(O)OR 3  groups, one or two C(O)NR 4 R 5  groups, one or two OR 7  groups or one or two NR 9 R 10  groups, or  
 benzyl optionally substituted on the phenyl ring with any combination of one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups or one C 3 -C 6 alkoxycarbonylalkyl group, and  
 when R 37  and R 38  are taken together with the atom to which they are attached, they represent a ring in which R 37 R 38  is a C 2 -C 6 alkylene group;  
 
 R 4  and R 5  are each independently hydrogen or C 1 -C 6 alkyl, and when R 4  and R 5  are taken together with the atom to which they are attached, they represent a ring in which R 4  and R 5  is a C 2 -C 6 alkylene group;  
 R 9  and R 10  are each independently hydrogen, C 1 -C 6 alkyl or C 3 -C 6 alkoxycarbonylalkyl, and when R 9  and R 10  are taken together with the atom to which they are attached, they represent a ring in which R 9 R 10  is a C 2 -C 6 alkylene group; and  
 A is O, N or S  
 which method comprises reacting a substituted carbodiimide having the structural formula  
                     
 wherein Q, R, X and Y are as described above with a compound having the structural formula  
                     
 wherein A, R 37  and R 38  are as described above.  
 
     
     
         38 . The method according to  claim 37  wherein the reaction is conducted in the presence of a catalyst.