5-SUBSTITUTED OXAZOLIDINES HAVING HERBICIDE ANTIDOTE ACTIVITY, PRODUCTION THEREOF, HERBICIDAL COMPOSITIONS CONTAINING THEM, USE THEREOF IN PREVENTING INJURY TO CROPS AND CROP SEEDS COATED THEREWITH
N-haloacyl oxazolidines substituted in the 5-position with oxy or thio containing groups of the formula A-Compounds: wherein XR1 is phenoxy, R is selected from the group consisting of haloalkyl, where halo is chloro or bromo, and p-methyl phenylsulfonylamido; and R2 and R3 are independently selected from lower alkyl; B-Compounds: wherein X is selected from the group consisting of oxygen and sulfur; R1 is selected from the group consisting of alkyl and alkenyl; R is selected from the group consisting of haloalkyl, alkylthio and p-tolylsulfonamido; R2 and R3 are independently selected from the group consisting of hydrogen and lower alkyl, each having 1 to 3 carbon atoms, inclusive; provided that the carbon content of R1 + R2 is less than or equal to 6 carbon atoms and further provided that when XR1 is alkylthio, then R is other than haloalkyl having 3 to 4 carbon atoms inclusive, and provided that when XR1 is methoxy, R is other than 2,3-dibromopropyl; and in addition a compound selected from the group of compounds consisting of 2,2-dimethyl-3(3-bromopropionyl)5-pentoxymethyl oxazolidine; 2,2-dimethyl-3(5-chlorovaleryl)5-isopropoxymethyl oxazolidine; 2,2-dimethyl-3(5-chlorovaleryl)-5-allyloxymethyl oxazolidine; C-Compounds: wherein X is oxygen or sulfur and R1 is alkyl; R is selected from the group consisting of haloalkyl, and alkoxy carboalkyl; R2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R3 is selected from the group consisting of hydrogen and methyl. These new compounds have utility as active herbicidal antidotes to protect against and decrease crop injury when used with thiolcarbamate herbicides, and may be when applied in various ways to achieve this. These ways include soil treatment, seed treatment and in-furrow treatment. Improved herbicidal compositions comprising a first-part of one or more thiolcarbamate herbicides and a second part of an effective antidote compound therefor as defined above are disclosed.
