Herbicidal imidazolidinetrione and thioxo-imidazolidinediones

A compound of the formula;

• wherein
• R is hydrogen, (C1-C8)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)alkynyl, (C1-C4)alkoxy(C1-C4)alkyl, (C3-C6)cycloalkoxy(C1-C4)alkyl, C2-C6)alkenyloxy(C1-C4)alkyl, (C3-C6)alkenyloxy(C1-C4)alkyl, C1-C12)alkylcaxbonyl, (C1-C4)alkoxycarbonyl, (C2-C6)alkenyloxycarbonyl, cyano, dialkylamino, or (C1-C6)alkylsulfonyl;,
• X1 is hydrogen or halo;
• X2 is halo, cyano, or nitro;
• X3 is (C1-C8)haloalkyl, (C1-C8)alkoxy, (C3-C6)cycloalkoxy, (C2-C6)alkenyloxy, (C3-C6)alkynyloxy, (C1-C12)alkylcarbonyl, (C1-C4)alkoxycarboryl, (C2-C6)alkenyloxycarbonyl, (C3-C6)alkyloxycarbonyl, (C1-C8)alkylsulfonylamino, (C1-C8)alkylsulfonylalkylamino, (C1-C4)alkoxycarbonylmethoxy, (C1-C4)alkoxycarbonylethoxy;
• or Q;
• wherein Q is
• wherein R1 is NH2, OH, or (C1-C4)alkyl;
• and
• X4 is hydrogen or halo;
• each W is independently oxygen or sulfur;
• or, when X1 is halo and X4 is hydrogen, then X2 and X3 may form a 5- or 6-membered heterocyclic ring fused to the phenyl ring to form a bicyclic moiety having the structure
• wherein
• L is oxygen or sulfur;
• R2 is hydrogen or (C1-C4)alkyl;
• R3 is hydrogen;
• (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C3-C6)alkynyl;
• (C1-C4)alkoxyalkyl;
• (C2-C6)alkenyloxyalkyl;
• (C3-C6)alkynyloxyalkyl;
• cyanoalkyl;
• amino, or hydroxy;
• and
• R4 is hydrogen, (C1-C3)alkyl or fluorine;
• or, when X1 and X2 are halo, then X3 and X4 form a 5- or 6-membered heterocyclic ring fused to the phenyl ring to which they are attached to form a bicyclic moiety having the structure
• wherein
• Y is oxygen, sulfur or —NR6 wherein R6 is hydrogen, (C1-C6)alkyl, (C3-C5)alkenyl or (C3-C6)alkynyl;
• Y is oxygen, sulfur, —NR6, or —CO;
• R5 is hydrogen, halo, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, or (C3-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, cyano, (C1-C6) hydroxyalkyl, —CO2R8, a formyl group, an acyl group, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkysulfonyl, or a carboxyl group;
• R6 is hydrogen, (C1-C6)alkyl, (C3-C6)alkenyl, or (C3-C6)alkynyl;
• R7 is hydrogen, halo, (C1-C6)alkyl (C1-C6)haloalkyl, an acyl group, or a nitro;
• and agronomically acceptable salts thereof.