Substituted oxazolidinones and imidazolinones as herbicides

A compound of Formula 1, all stereoisomers, N-oxides, and salts thereof

• wherein
• Y is O or NH;
• Z is selected from a group of a fully saturated, or a fully or partly unsaturated, five membered rings as shown below, optionally substituted by group Rv
• m is 0, 1 or 2;
• Rv is halogen, cyano, CO2R8, or (C1-C2)-alkyl or (C1-C2)-alkoxy, each of which is substituted by n radicals independently selected from the group consisting of halogens;
• each R is independently H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, S(O)pR7 or CO2R8;
• n is 0, 1, 2, 3, 4 or 5;
• p is 0, 1 or 2;
• V and W are each independently O or S;
• X is a direct bond, O, S or NR6;
• R1 and R2 are each independently hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 cyanoalkoxy;
• R3 is H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C2-C5 alkenyloxy, C2-C5 alkynyloxy, C3-C7 cycloalkoxy, C3-C7 cycloalkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C6 haloalkyl, C2-C5 haloalkenyl, C2-C5 haloalkynyl, C2-C5 alkoxyalkyl, C2-C5 haloalkoxyalkyl, C1-C5 alkoxy, C1-C6 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonate, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C5 alkoxycarbonyl, optionally each of which is further substituted by at least one radical from the group consisting of halogen, cyano, C1-C4 alkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, and hydroxy;
• R4 is independently H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;
• or W1G1;
• W1 is a direct bond, C1-C4 alkanediyl or C1-C4 alkenediyl;
• G1 is S(O)pR7, SO2NR10R11, CO2R8, CONR10R11 or COR12;
• R5 is H, C1-C12 alkyl, NH2, N═CR8R12, C3-C7 cycloalkyl, C3-C12 cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2)qS(O)pR7, (CH2)qOR9, (CH2)qCOR12, each of which is optionally substituted by one or more radicals from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, hydroxy and aryl;
• q is 0, 1, 2, 3, 4 or 5;
• R6 is hydrogen, cyano, OR9, S(O)pR7, SO2NR10R11, CO2R8, CONR10R11, COR12, NR10R11, NR10COR12, NR10CONR10R11, NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)═NOR9, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl;
• or
• R6 is C1-C12 alkyl, C3-C8 cycloalkyl, C4-C12 cycloalkylalkyl, C2-C12 alkenyl, C5-C7 cycloalkenyl or C2-C12 alkynyl, each of which is optionally substituted by one or more radicals from the group consisting of halogen, cyano, nitro, OR9, S(O)pR7, SO2NR10R11, CO2R8, CONR10R11, COR12, NR10R11, NR10COR12, NR10CONR10R11, NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)═NOR9, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl;
• or
• R5 and R6 can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, OR9, S(O)pR7, SO2NR10R11, CO2R8, CONR10R11, COR12, NR10R11, NR10COR12, NR10CONR10R11, NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)═NOR9;
• R7, R8, R9, R10, R11 and R12 are each independently H, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C3-C7 cycloalkyl or aryl, each of which is optionally substituted by one or more radicals from the group consisting of F, Cl, C1-C2 alkoxy or aryl.