FIELD OF THE INVENTION

This disclosure relates to certain pyrimidinyloxy benzo-fused compounds, N-oxides thereof, and salts of the compounds and N-oxides; compositions comprising such compounds, N-oxides and salts; processes for making such compounds, N-oxides, salts and compositions; and methods for using such compounds, N-oxides, salts and compositions to control undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

SUMMARY OF THE INVENTION

This disclosure relates, in part, to compounds of Formula 1 (including all geometric and stereoisomers), N-oxides of such compounds, and salts of such compounds and N-oxides:


whereinK together with the two contiguous linking carbon atoms forms a 4-, 5- or 6-membered ring selected from the group consisting of K-1, K-2, K-3, K-4, K-5, K-6, K-7, K-8, K-9, K-10, K-11, K-12, K-13, K-14, K-15, K-16 and K-17:

R is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6halocycloalkylalkyl, C4-C8alkylcycloalkyl, C4-C8cycloalkylalkyl, C1-C6alkylamino, C1-C6haloalkylamino, C2-C10dialkylamino, C2-C10halodialkylamino, C3-C6cycloamino, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C3-C6haloalkenyloxy, C3-C6haloalkynyloxy, C3-C6cycloalkoxy, C3-C6halocycloalkoxy, C4-C8cycloalkylalkoxy, C4-C8halocycloalkylalkoxy, C2-C6alkoxyalkyl, C2-C6haloalkoxyalkyl, C2-C6alkoxyhaloalkyl, C2-C6alkoxyalkoxy, C2-C6cyanoalkyl, C2-C6cyanoalkoxy, C3-C7cyanoalkoxyalkyl, C1-C6hydroxyalkyl, C1-C6nitroalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C3-C8cycloalkylthio, C1-C6alkenylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8cycloalkylsulfonyl, C2-C6alkylthioalkyl, C2-C6haloalkylthioalkyl, benzyl, —N(R5)(OR6), —ON(R7a)(R7b) or —N(R5)N(R7a)(R7b);each R1ais hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C2-C6alkenyl, C2-C6alkynyl, hydroxy, C1-C4alkoxy, C1-C4haloalkoxy, cyano or S(O)pR8;each R1bis independently selected from halogen, C1-C4alkyl, C1-C4haloalkyl, C2-C6alkenyl, C2-C6alkynyl, hydroxy, C1-C4alkoxy, C1-C4haloalkoxy, cyano and S(O)pR8;each R1cis independently selected from hydrogen, F, C1-C4alkyl, C1-C4haloalkyl, C2-C6alkenyl, C2-C6alkynyl, hydroxy, C1-C4alkoxy, C1-C4haloalkoxy, cyano and S(O)pR8;R2is halogen, cyano, nitro, C1-C6alkoxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl or S(O)qR9;each R3is independently halogen, cyano, nitro, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C4haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C4-C8alkylcycloalkyl, C4-C8cycloalkylalkyl, C2-C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C3-C7cycloalkylcarbonyl, C2-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, C1-C4haloalkoxy, C3-C6cycloalkoxy, C3-C6halocycloalkoxy, C4-C8cycloalkylalkoxy, C2-C6alkoxyalkyl, C2-C6haloalkoxyalkyl, C2-C6alkoxyhaloalkyl, C2-C6alkoxyalkoxy, C2-C4alkylcarbonyloxy, C2-C6cyanoalkyl, C2-C6cyanoalkoxy or C2-C4alkylthioalkyl;m is 0, 1, 2 or 3;each n is independently selected from 0 and 1;p is 0, 1 or 2;q is 0, 1 or 2;r is 0, 1 or 2;Z is O or S;R4is nitro, C1-C6alkoxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl or S(O)rR9;R5is C1-C6alkyl or C1-C6haloalkyl;R6is H, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C2-C6haloalkoxyalkyl or C2-C6cyanoalkyl;each R7aand R7bis independently H, C1-C6alkyl or C1-C6haloalkyl;R8is C1-C6alkyl or C1-C6haloalkyl; andR9is independently C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylamino or C2-C10dialkylamino.

This disclosure also relates, in part, to an agricultural composition (generally herbicidal) comprising such a compound, N-oxide or salt in a herbicidally effective amount and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents, the composition optionally further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.

This disclosure also relates, in part, to an herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) through (b16); and salts of compounds of (b1) through (b16), as described below.

This disclosure also relates, in part, to processes for making the above-identified compounds, N-oxides, salts and compositions.

This disclosure also relates, in part, to methods for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of an above-identified compound, N-oxide, salt or composition.

