2-(2-imidazolin-2-yl)-pyridines and quinolines 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 the plants or to soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of a compound having a structure:
• ##STR285## wherein 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 R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
• A is COOR.sub.3, CONHR.sub.6, CHO, CH.sub.2 OH, COCH.sub.3, COC.sub.6 H.sub.5, CN, CH.sub.3, CH.dbd.NOH, CH.sub.2 COOH, CONHOH, CH.sub.2 CH.sub.2 COOH, CHR.sub.8 OH, ##STR286## R.sub.3 is hydrogen, ##STR287## C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium halide;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C.sub.1 -C.sub.3 alkoxy groups or two 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.16 alkynyl;
• or
• A cation;
• R.sub.6 is hydrogen, hydroxyl, C.sub.3 -alkenyl, C.sub.3 -alkynyl or C.sub.1 -C.sub.4 alkyl optionally substituted with one hydroxyl or one chlorine group;
• B is H, COR.sub.4 or SO.sub.2 R.sub.5, provided that when B is COR.sub.4 or SO.sub.2 R.sub.5, A is CH.sub.3, CN, or COOR.sub.3 in which R.sub.3 is other than H or a cation, W is O;
• and Y and Z are not alkylamino, hydroxyl, or hydroxyloweralkyl;
• R.sub.4 is C.sub.1 -C.sub.11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with one methyl group;
• W is O or S;
• R.sub.8 is C.sub.1 -C.sub.4 -alkyl or phenyl;
• X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure:
• --(CH.sub.2).sub.n --, where n is 3 or 4, x is hydrogen;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, hydroxyloweralkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino or C.sub.1 -C.sub.4 alkylsulfonyl group, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• and, when taken together, Y and Z may form a ring in which YZ are represented by the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 3 or 4, provided that X is hydrogen;
• or ##STR288## where L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, Q or R.sub.7 may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• and the N-oxides thereof when W is O and A is CN, CH.sub.3 or COOR.sub.3, provided that in the N-oxides R.sub.3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio;
• and when R.sub.1 and R.sub.2 represent different substituents, the optical isomers thereof, and, except when R.sub.3 is a cation, the acid addition salts thereof.

A method for defoliating cotton plants comprising applying to the foliage of the plants, approximately five to fifteen days prior to anticipated harvest, a desiccating and defoliating amount of a compound having the structure:

• ##STR292## wherein 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 R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
• A is COOR.sub.3, CONHR.sub.6, CHO, CH.sub.2 OH, COCH.sub.3, COC.sub.6 H.sub.5, CN, CH.sub.3, CH.dbd.NOH, CH.sub.2 COOH, CONHOH, CH.sub.2 CH.sub.2 COOH, CHR.sub.8 OH, ##STR293## R.sub.3 is hydrogen, ##STR294## C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium halide;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C.sub.1 -C.sub.3 alkoxy groups or two 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.16 alkynyl;
• or,
• A cation;
• R.sub.6 is hydrogen, hydroxyl, C.sub.3 -alkenyl, C.sub.3 -alkynyl or C.sub.1 -C.sub.4 alkyl optionally substituted with one hydroxyl or one chlorine group;
• B is H, COR.sub.4 or SO.sub.2 R.sub.5, provided that when B is COR.sub.4 or SO.sub.2 R.sub.5, A is CH.sub.3, CN, or COOR.sub.3 in which R.sub.3 is other than H or a cation;
• W is O;
• and Y and Z are not alkylamino, hydroxyl;
• or hydroxyloweralkyl;
• R.sub.4 is C.sub.1 -C.sub.11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with one methyl group;
• W is O or S;
• R.sub.8 is C.sub.1 -C.sub.4 -alkyl or phenyl;
• X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure:
• --(CH.sub.2).sub.n --, where n is 3 or 4, X is hydrogen;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, hydroxyloweralkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino or C.sub.1 -C.sub.4 alkylsulfonyl group, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• and, when taken together, Y and Z may form a ring in which YZ are represented by the structure:
• -(CH.sub.2).sub.n -, where n is an integer of 3 or 4, provided that X is hydrogen;
• or ##STR295## where L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, Q or R.sub.7 may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• and the N-oxides thereof when W is O and A is CN, CH.sub.3 or COOR.sub.3, provided that R.sub.3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio;
• and when R.sub.1 and R.sub.2 represent different substituents, the optical isomers thereof, and, except when R.sub.3 is a cation, the acid addition salts thereof.

A herbicidal composition comprising an inert solid or liquid diluent and a herbicidally effective amount of a compound having a structure:

• ##STR296## wherein 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 R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
• A is COOR.sub.3, CONHR.sub.6, CHO, CH.sub.2 OH, COCH.sub.3, COC.sub.6 H.sub.5, CN, CH.sub.3, CH.dbd.NOH, CH.sub.2 COOH, CONHOH, CH.sub.2 CH.sub.2 COOH, CHR.sub.8 OH, ##STR297## R.sub.3 is hydrogen, ##STR298## C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium halide;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C.sub.1 -C.sub.3 alkoxy groups or two halogen groups:
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -CH.sub.3 alkyl groups;
• C.sub.3 -C.sub.16 alkynyl;
• or,
• A cation;
• R.sub.6 is hydrogen, hydroxyl, C.sub.3 -alkenyl, C.sub.3 -alkynyl or C.sub.1 -C.sub.4 alkyl optionally substituted with one hydroxyl or one chlorine group;
• B is H, COR.sub.4 or SO.sub.2 R.sub.5, provided that when B is COR.sub.4 or SO.sub.2 R.sub.5, A is CH.sub.3, CN, or COOR.sub.3 in which R.sub.3 is other than H or a cation;
• W is O;
• and Y and Z are not alkylamino, hydroxyl, or hydroxyloweralkyl;
• R.sub.4 is C.sub.1 -C.sub.11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with one methyl group;
• W is O or S:
• R.sub.8 is C.sub.1 -C.sub.4 -alkyl or phenyl;
• X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure:
• --(CH.sub.2).sub.n --, where n is 3 or 4, X is hydrogen;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, hydroxyloweralkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino or C.sub.1 -C.sub.4 alkylsulfonyl group, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• and, when taken together, Y and Z may form a ring in which YZ are represented by the structure:
• --(CH.sub.2)n --, where n is an integer of 3 or 4, provided that X is hydrogen;
• or ##STR299## where L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, Q or R.sub.7 may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• and the N-oxides thereof when W is O and A is CN, CH.sub.3 or COOR.sub.3, provided that R.sub.3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkythio;, and when R.sub.1 and R.sub.2 represent different substituents, the optical isomers thereof, and, except when R.sub.3 is a cation, the acid addition salts thereof.