Substituted imidazolinyl nicotine acids, esters and salts and use thereof as herbicidal agents

Claim 2

A compound having the structure selected from the group consisting of: 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 OH, 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 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; 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 l -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 one 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, 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 3 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 l -C 4 alkyl or phenyl optionally substituted with one methyl group, W is 0 or S; Rg 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 alkox y , C 1 -C 4 alkylthio, phenoxy, C I -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 alkox y, C 1 -C 4 alk y lthio, 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 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 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 7

A herbicidal composition comprising an inert solid or liquid diluent and a herbicidally effective amount of a compound having a structure selected from the group consisting of: 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 OH, COCH 3 , COC 6 H 5 , CN, CH 3 , CH=NOH, CH 2 COOH, CONH OH , CH 2 CH 2 COOH, CHR 8 CH, R 3 is hydrogen, diloweralkylimino 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; 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 l -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 14 alkynyl optionally substituted with one or two C 1 -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, 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 H 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; R4 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 Q 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 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 -haloalkyl, nitro, cyano, C I -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 alkoxy, C 1 -C 4 alk y lthio , Cl - C4 alkylsulfonyl, C l - 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 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 8

A herbicidal composition comprising an inert solid or liquid diluent and a herbicidally effective amount of a compound having a structure selected from the group consisting of: 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 OH, COCH 3 , COC 6 H 5 , CN, CH 3 , CH=NOH, CH 2 COOH, CONH OH , CH 2 CH 2 COOH, CHR 8 CH, R 3 is hydrogen, diloweralkylimino 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; 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 l -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 14 alkynyl optionally substituted with one or two C 1 -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, 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 H 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; R4 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 Q 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 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 -haloalkyl, nitro, cyano, C I -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 alkoxy, C 1 -C 4 alk y lthio , Cl - C4 alkylsulfonyl, C l - 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 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 9

A solid herbicidal composition according to Claim 7 , comprising from 20% to 45% by weight of a finely divided solid inert carrier; from 45% to 80% by weight of the herbicidally effective ingredient represented by structures a, b, C, d and. e; from about 2$ to 5$ by weight of a dispersing agent and from about 2% to 5% by weight of a surface active agent.

Claim 10

A liquid herbicidal composition according to Claim 7 , comprising from 5% to 25% by weight of the herbicidally effective ingredient represented by structures a, b, c, d and e; from about 85% to 90% by weight of an inert organic solvent and from about 5% to 10% by weight of a surface active agent.

Claim 11

A granular herbicidal composition according to Claim 7 , comprising from about 80% to 97% by weight of an. inert granular carrier and from about 3% to 20% by weight of the herbicidally effective ingredient represented by structures a, b, c, d and e.

Claim 12

A process for the preparation of 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 merthyl; A is COOR 3 or CONHR 6 ; R3 is C 1 -C 12 alkyl optionally substituted with one 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, halopnenyl,k loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycartonyl 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 one or two C 1 -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, C 3 -alkynyl or C 1 -C 4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H; W is Q; 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 strutture -(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 1 -C 6 alkoxy, C l -C 4 alkylthio, phenoxy, C l -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 l -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 alkox y, C 1 -C 4 alkylthio, C l -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. Comprising; reacting a compound having the structure: wherein R 1 , R 2 , X, Y and Z are as described above; with (a) at least one equivalent of an alcohol represented by the structure R 3 OH and an alkali - metal alkoxide R 3 0 M, where R 3 is as described above and M is an alkali metal, at a temperature O O between about 20 C and 50 C, alone or in the presence of an aprotic solvent; whereby the desired product, in which A is COOR 3 and R 3 , R 1 , R 2 , X, Y and Z are as described above, is formed; or with (b) at least one equivalent of an amine represented by thee structure R 6 NH 2 , where R 6 is as described above, alone or in the presence of an aprotic solvent, ' at a temperature between about 80°C and o 125 C, whereby the desired product, in which A is CONHR 6 and. R 6 , R 1 ,R 2 , X, Y and Z are as described above, is formed.

Claim 13

A process for the preparation of 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 merthyl; A is COOR 3 or CONHR 6 ; R3 is C 1 -C 12 alkyl optionally substituted with one 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, halopnenyl,k loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycartonyl 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 one or two C 1 -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, C 3 -alkynyl or C 1 -C 4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H; W is Q; 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 strutture -(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 1 -C 6 alkoxy, C l -C 4 alkylthio, phenoxy, C l -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 l -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 alkox y, C 1 -C 4 alkylthio, C l -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. Comprising; reacting a compound having the structure: wherein R 1 , R 2 , X, Y and Z are as described above; with (a) at least one equivalent of an alcohol represented by the structure R 3 OH and an alkali - metal alkoxide R 3 0 M, where R 3 is as described above and M is an alkali metal, at a temperature O O between about 20 C and 50 C, alone or in the presence of an aprotic solvent; whereby the desired product, in which A is COOR 3 and R 3 , R 1 , R 2 , X, Y and Z are as described above, is formed; or with (b) at least one equivalent of an amine represented by thee structure R 6 NH 2 , where R 6 is as described above, alone or in the presence of an aprotic solvent, ' at a temperature between about 80°C and o 125 C, whereby the desired product, in which A is CONHR 6 and. R 6 , R 1 ,R 2 , X, Y and Z are as described above, is formed.

Claim 14

A process for the preparation of 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 , CH 2 OH, COCH 3 COC 6 H 5 , or R 3 is diloweralkylimino 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; 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 10 alkynyl optionally-substituted with one or two C 1 -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 aliphatic ammonium; 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; W is 0; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that whenm y and 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 1 -C 6 alko xy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 -haloalkyl, nitro, cyano, C 1 -C 4 alkylamino, dilowetalkylamino 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 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C l -C 4 haloalkyl, NO 2 , CN, phenyl, phenoxy, amino, C l -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. comprising, reacting a compound having the structure: wherein R 1 , R 2 , X, Y and Z. are as described above; with a) at least one equivalent of an alcohol represented by the structure R 3 OH and an alkali metal alkoxide R 3 O θM + , where R 3 is as described above and M is an alkali metal, alone or in the presence of an aprotic solvent at a temperature between 20°C and 50°C, whereby the desired productin which A is COOR 3 and R 3 , R 1 , R 2 , X, Y and Z are as described above, is obtained; b) at least one equivalent of an amine represented by the structure R 6 NH 2 , where R 6 is as described above, in the presence of a loweralkyl alcohol or an aprotic solvent at a temperature between about 80°C and 125°C, whereby the desired product,in which A is CONHR 6 and R 6 , R 1 , R 2 , X, Y and Z are as described above, is obtained; c) at least one equivalent of methyl magnesium bromide, in the presence of an aprotic solvent at a temperature between -50°C and -80°C under a blanket of inert gas, whereby the desired product in which A is COCH 3 and R 1 , R 2 , X, Y and Z are as described above, is obtained; d) at least one equiyalent phenyl lithium in the presence of an aprotic solvent at a temperature between -50°C and -80°C under a blanket of inert gas, whereby the desired product, in which A is COC 6 H 5 and R 1 , R 2 , X, Y and Z are as described above, is obtained; or e) at least one equivalent of trimethylphosponoacetate, in the presence of an aprotic solvent at -50°C to -80°C under a blanket of inert gas, whereby the desired product in which A is and R 1 , R 2 , X, Y and Z are as described above, is obtained; or f) at least one equivalent of sodium borohydride in ethanol at -10° to +20°C whereby the desired product in which A is CH 2 OH, is obtained.

Claim 15

A process for the preparation of 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 , CH 2 OH, COCH 3 COC 6 H 5 , or R 3 is diloweralkylimino 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; 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 10 alkynyl optionally-substituted with one or two C 1 -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 aliphatic ammonium; 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; W is 0; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that whenm y and 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 1 -C 6 alko xy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 -haloalkyl, nitro, cyano, C 1 -C 4 alkylamino, dilowetalkylamino 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 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C l -C 4 haloalkyl, NO 2 , CN, phenyl, phenoxy, amino, C l -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. comprising, reacting a compound having the structure: wherein R 1 , R 2 , X, Y and Z. are as described above; with a) at least one equivalent of an alcohol represented by the structure R 3 OH and an alkali metal alkoxide R 3 O θM + , where R 3 is as described above and M is an alkali metal, alone or in the presence of an aprotic solvent at a temperature between 20°C and 50°C, whereby the desired productin which A is COOR 3 and R 3 , R 1 , R 2 , X, Y and Z are as described above, is obtained; b) at least one equivalent of an amine represented by the structure R 6 NH 2 , where R 6 is as described above, in the presence of a loweralkyl alcohol or an aprotic solvent at a temperature between about 80°C and 125°C, whereby the desired product,in which A is CONHR 6 and R 6 , R 1 , R 2 , X, Y and Z are as described above, is obtained; c) at least one equivalent of methyl magnesium bromide, in the presence of an aprotic solvent at a temperature between -50°C and -80°C under a blanket of inert gas, whereby the desired product in which A is COCH 3 and R 1 , R 2 , X, Y and Z are as described above, is obtained; d) at least one equiyalent phenyl lithium in the presence of an aprotic solvent at a temperature between -50°C and -80°C under a blanket of inert gas, whereby the desired product, in which A is COC 6 H 5 and R 1 , R 2 , X, Y and Z are as described above, is obtained; or e) at least one equivalent of trimethylphosponoacetate, in the presence of an aprotic solvent at -50°C to -80°C under a blanket of inert gas, whereby the desired product in which A is and R 1 , R 2 , X, Y and Z are as described above, is obtained; or f) at least one equivalent of sodium borohydride in ethanol at -10° to +20°C whereby the desired product in which A is CH 2 OH, is obtained.