2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents

Claim 1

A compound having the structure: ##STR279## wherein R 1 is C 1 -C 4 alkyl; R 2 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and when R 1 and R 2 are taken together with the carbon to which they are attached they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl; A is COOR 3 , CONHR 6 , CHO, CH 2 CH, COCH 3 , COC 6 H 5 , CN, CH 3 , CN═NOH, CH 2 COOH, CONHOH, CH 2 CH 2 COOH, CHR 8 OH, ##STR280## R 3 is hydrogen, ##STR281## C 1 -C 12 alkyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, halogen, hydroxyl, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium halide; C 3 -C 12 alkenyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C 1 -C 3 alkoxy groups or two halogen groups; C 3 -C 6 cycloalkyl optionally substituted with one or two C 1 -C 3 alkyl groups; C 3 -C 6 alkynyl; or, A cation; R 6 is hydrogen, hydroxyl, C 3 -alkenyl, C 3 -alkynyl or C 1 -C 4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR 4 or SO 2 R 5 , provided that when B is COR 4 or SO 2 R 5 , A is CH 3 , CN, or COOR 3 in which R 3 is other than H or a cation; W is O; and Y and Z are not alkylamino, hydroxyl, or hydroxylower alkyl; R 4 is C 1 -C 11 alkyl, chloromethyl or phenyl optionally, substituted with one chloro, one nitro or one methoxy group; R 5 is C 1 -C 4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; R 8 is C 1 -C 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 2 ) n --, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C 1 -C 6 alkyl, hydroxyloweralkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 haloalkyl, nitro, cyano, C 1 -C 4 alkylamino, diloweralkylamino or C 1 -C 4 alkylsulfonyl group, or phenyl optionally substituted with one C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: --(CH 2 ) n --, where n is an integer of 3 or 4, provided that X is hydrogen; or ##STR282## where L, M, Q and R 7 are each hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, NO 2 , CN, phenyl, phenoxy, amino, C 1 -C 4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one C1, CF 3 , NO 2 or CH 3 group, with the proviso that only one of L, M, Q or R 7 may represent a substituent other than hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and the N-oxides thereof when W is O and A is CN, CH 3 , or COOR 3 provided that in the N-oxides R 3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkythio, and when R 1 and R 2 represent different substituents, the optical isomers thereof, and, except when R 3 is a cation, the acid addition salts thereof.

Claim 33

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

Claim 34

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

Claim 53

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

Claim 54

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