(2-imidazolin-2-yl) fused heteropyridine compounds, intermediates for the preparation of and use of said compounds as herbicidal agents

A method for the control of monocotyledonous and dicotyledonous annual, perennial and aquatic plant species comprising:

• applying to the foliage of said plants or to soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of compounds having structures II or IV ##STR405## wherein A is COOR.sub.8, CHO, CH.sub.2 OH, COCH.sub.2 OH, CONH.sub.2, CH.sub.2 CH.sub.2 OH, CONHOH or ##STR406## R.sub.C and R.sub.D are each hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.8 is hydrogen, C.sub.1 -C.sub.4 alkyl which may be interrupted by O or S, or is optionally substituted with C.sub.1 -C.sub.4 alkoxy, halogen, hydroxy, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, furfuryl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.4 alkoxy carbonyl, cyano or C.sub.1 -C.sub.4 trialkylammonium;
• C.sub.3 -C.sub.6 alkenyl, optionally substituted with one or two C.sub.1 -C.sub.3 alkoxy, phenyl or halogen groups, C.sub.3 -C.sub.6 cycloalkyl, optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• C.sub.3 -C.sub.10 alkynyl, optionally substituted with phenyl, halogen, C.sub.1 -C.sub.4 alkoxy;
• or a cation selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, ammonium and organic ammonium;
• B is H, COR.sub.9 or SO.sub.2 R.sub.10, R.sub.9 is C.sub.1 -C.sub.11 alkyl, chloromethyl, C.sub.1 -C.sub.4 alkoxyl or phenyl optionally substituted with one chloro, one nitro, one methyl, or one methoxy group;
• R.sub.10 is C.sub.1 -C.sub.5 alkyl, phenyl, or phenyl substituted with one methyl, halogen, nitro or C.sub.1 -C.sub.4 alkoxy;
• R.sub.1 is C.sub.1 -C.sub.4 alkyl;
• R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl;
• and when taken together with the carbon to which they are attached, R.sub.1 and R.sub.2 may represent C.sub.3 -C.sub.6 cycloalkyl, optionally substituted with methyl;
• represents a single or double bond;
• W is O or S;
• X.sub.1, X.sub.2, and X.sub.4 are any combination of CR.sub.4, CR.sub.5 R.sub.6, N or NR.sub.3 and are the same or different, with the proviso that one of X.sub.1, X.sub.2 and X.sub.4 must be N or NR.sub.3 and two of X.sub.1, X.sub.2 and X.sub.4 must be CR.sub.4 or CR.sub.5 R.sub.6 ;
• Y.sub.1 and Y.sub.2 are N or CR.sub.4 ;
• Z.sub.1 is NR.sub.3 or CR.sub.5 R.sub.6 with the proviso that if Z.sub.1 is NR.sub.3 then Y.sub.1 and Y.sub.2 are CR.sub.4 and are the same or different and if Z.sub.1 is CR.sub.5 R.sub.6 then one of Y.sub.1 and Y.sub.2 must be N and the other is CR.sub.4 ;
• R.sub.3 is C.sub.1 -C.sub.4 alkyl, which may be optionally substituted with phenyl or one or more halogens;
• C.sub.3 -C.sub.6 alkenyl, optionally substituted with phenyl or one or more halogens;
• C.sub.3 -C.sub.6 alkynyl, optionally substituted with phenyl or halogen;
• C.sub.1 -C.sub.4 alkoxy, optionally substituted with phenyl or one or more halogens;
• C.sub.3 -C.sub.6 alkenyloxy optionally substituted with phenyl or one or more halogens;
• C.sub.3 -C.sub.6 alkynyloxy optionally substituted with halogen or phenyl;
• or C.sub.2 -C.sub.6 alkanoyloxy, optionally substituted with halogen or phenyl;
• R.sub.4 is hydrogen;
• halogen;
• C.sub.1 -C.sub.6 alkyl;
• C.sub.1 -C.sub.4 alkoxy;
• C.sub.2 -C.sub.6 alkanoyloxy;
• C.sub.1 -C.sub.4 alkylthio;
• phenoxy;
• C.sub.1 -C.sub.4 haloalkyl;
• C.sub.1 -C.sub.4 haloalkoxy;
• nitro;
• C.sub.1 -C.sub.4 alkoxycarbonyl;
• C.sub.1 -C.sub.4 dialkylamino;
• C.sub.1 -C.sub.4 alkylsulfonyl or phenyl, optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or C.sub.1 -C.sub.4 haloalkyl;
• R.sub.5 and R.sub.6 are each hydrogen;
• C.sub.1 -C.sub.4 alkyl;
• C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy;
• nitro;
• C.sub.1 -C.sub.4 alkylsulfonyl or phenyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or C.sub.1 -C.sub.4 haloalkyl;
• or any combination of these groups except when R.sub.5 and R.sub.6 are the same group, they are either both hydrogen or both C.sub.1 -C.sub.4 alkyl;
• and when taken together, R.sub.5 and R.sub.6 may form a ring in which R.sub.5 R.sub.6 are represented by the structure --(CH.sub.2).sub.n-- where n is an integer of 4 or 5, or when taken together, R.sub.5 and R.sub.6 may form a group .dbd.O or .dbd.NR.sub.7 wherein R.sub.7 is phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylamino;
• R.sub.3, R.sub.4, R.sub.5 and R.sub.6, when present on adjacent positions may, along with the atoms to which they are attached, form a ring and such R.sub.3 -R.sub.6 pairs can be represented by the structure --(CH.sub.2).sub.m -- or --(CH).sub.m -- where m is an integer of 3 or 4;
• with the provisos that
• represents a single bond between:
• X.sub.1 and X.sub.2 when either X.sub.1 or X.sub.2 is NR.sub.3 or CR.sub.5 R.sub.6 ;
• and X.sub.2 and X.sub.4 when either X.sub.2 or X.sub.4 is NR.sub.3 or CR.sub.5 R.sub.6 ;
• and
• when B is COR.sub.9 or SO.sub.2 R.sub.10 and R.sub.8 is hydrogen, then represents an aromatic bond, R.sub.3 is C.sub.1 -C.sub.4 alkyl, and R.sub.4, R.sub.5 and R.sub.6 may not be halogen.