Method to beneficially influence & alter the development & life cycle of agronomic and horticultural crops with certain imidazolinyl nicotinic acids and derivatives thereof

Claim 1

A method to increase axillary branching, tillering, flowering and yield of agronomic and horticultural crops and accelerate maturation of cereal crops comprising: applying to said crops plants or to soil containing the seeds or other propagating organs of said plants, a compound.having the structure: 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 they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl; A is COOR 3 , CONHR 6 , CHO, CH 2 0H, COCH 3 , COC 6 H 5 CN, CH 3 , CH=NOH , CH 2 COOH, CONHOH, CH 2 CH 2 COOH, CHR 8 OH, R 3 is hydrogen, diloweralkylimino C 1 -C 2 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; 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 l -C 3 alkyl groups; C 3 -C 10 alkynyl optionally substituted with cne or two C l -C 3 alkyl groups; or, A cation selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; R 6 is hydrogen, hydroxyl, C 3 -alkenyl, C3-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 COOR 3 in which R 3 is other than H, or a salt-forming cation, CH 3 or CN; W is 0; 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 0 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 each represent members selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, hydroxy-loweralkyl, C l -C 6 alko xy, 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 selected from 3 and 4, provided that X is hydrogen; or where L, M, Q and R 7 each represent members selected from the group consisting of hydrogen, halogen, C 1 C 4 alkyl, C 1 C 4 al k o xy, 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 , N0 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 when W is 0 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 the N-oxides thereof, and when R 1 and R 2 are not the same, the optical isomers thereof, and, except when R 3 is a salt-forming cation, the acid addition salts thereof.

Claim 2

A method to increase axillary branching, tillering, flowering and yield of agronomic and horticultural crops and accelerate maturation of cereal crops comprising: applying to said crops plants or to soil containing the seeds or other propagating organs of said plants, a compound.having the structure: 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 they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl; A is COOR 3 , CONHR 6 , CHO, CH 2 0H, COCH 3 , COC 6 H 5 CN, CH 3 , CH=NOH , CH 2 COOH, CONHOH, CH 2 CH 2 COOH, CHR 8 OH, R 3 is hydrogen, diloweralkylimino C 1 -C 2 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; 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 l -C 3 alkyl groups; C 3 -C 10 alkynyl optionally substituted with cne or two C l -C 3 alkyl groups; or, A cation selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; R 6 is hydrogen, hydroxyl, C 3 -alkenyl, C3-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 COOR 3 in which R 3 is other than H, or a salt-forming cation, CH 3 or CN; W is 0; 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 0 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 each represent members selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, hydroxy-loweralkyl, C l -C 6 alko xy, 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 selected from 3 and 4, provided that X is hydrogen; or where L, M, Q and R 7 each represent members selected from the group consisting of hydrogen, halogen, C 1 C 4 alkyl, C 1 C 4 al k o xy, 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 , N0 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 when W is 0 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 the N-oxides thereof, and when R 1 and R 2 are not the same, the optical isomers thereof, and, except when R 3 is a salt-forming cation, the acid addition salts thereof.