Patent EP-0008624-A1 (EP)
Inventor: REMPFLER HERMANN DR
IPC: A01N43/40
Filed: 1979-06-29
Abstract: For the Contracting States : BE, CH, DE, FR, GB, IT, NL 1. O-(Pyridyloxy-phenyl)-lactic acid ester of the formula I  see diagramm : EP0008624,P14,F1  in which "Hal" is a halogen atom, X is hydrogen or a halogen atom, Y is an oxygen or sulfur atom, Z is a C1 -C4 -alkylene group which is unsubstituted or substituted by methyl, ethyl, cyano, methylcarbonyl or by a group -COQ, Q is a group -OR1 , -SR2  or -NR3 R4 , wherein R1  and R2  independently of one another are each hydrogen or the cation equivalent of a base 1/n M**n(cation), wherein M is an n-valent alkali metal cation or alkaline earth metal cation, or an Fe, Cu, Zn, Mn or Ni cation, or an ammonium group  see diagramm : EP0008624,P15,F2  n as an integer 1, 2 or 3 corresponds to the valency of the cation, whilst Ra , Rb , Rc and Rd  independently of one another were each hydrogen, benzyl, or a C1 -C4 -alkyl group which is unsubstituted or substituted by -OH, -NH2  or C1 -C4 -alkoxy ; or R1  and R2  independently of one another are each C1 -C18 -alkyl group which is unsubstituted or is substituted by halogen, nitro, cyano, C1 -C8 -alkoxy, C2 -C8 -alkoxy-alkoxy, C3 -C6 -alkenyloxy, C1 -C8 -alkylthio, C2 -C8 -alkanoyl, C2 -C8 -acyloxy, C2 -C8 -alkoxycarbonyl, carbamoyl, bis-(C1 -C4 -alkyl)-amino, tris-(C1 -C4 -alkyl)-ammonium, C3 -C8 -cycloalkenyl, or by a phenyl, phenoxy or 5-6-membered heterocyclic radical having 1 to 3 hetero atoms, each of which is unsubstituted or for its part is mono- or polysubstituted by halogen, C1 -C4 -alkyl or C1 -C4 -alkoxy ; or they are each a C3 -C18 -alkenyl group which is unsubstituted or is mono- or tetrasubstituted by halogen or is mono- substituted by phenyl or methoxycarbonyl ; or they are a C3 -C8 -alkynyl group ; or a C3 -C12 -cycloalkyl group which is unsubstituted or is substituted by halogen or C1 -C4 -alkyl ; or they are each a C3 -C8 -cycloalkenyl group ; or a phenyl group which is unsubstituted or is mono- or polysubstituted by halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, NO2 , CF3 , COOH, CN, OH, SO3 H, NH2  or -NH(C1 -C4 -alkyl) or -N(C1 -C4 -alkyl)2  ; or R1  and R2  are each a 5- to 6-membered heterocyclic ring having 1 to 3 hetero atoms, and R3  and R4  independently of one another are each hydrogen, or C1 -C4 -alkyl which is unsubstituted or is substituted by chlorine, cyano, hydroxyl or C1 -C4 -alkoxy, or they are each C3 -C4 -alkenyl and R3  is also C3 -C4 -alkynyl, C1 -C4 -alkoxy, phenyl or benzyl, or R3  and R4  together with the nitrogen atom to which they are attached also form a 5-6-membered heterocycle which can contain oxygen, sulfur or a group  see diagramm : EP0008624,P15,F3 wherein R5  is hydrogen, C1 -C4 -alkyl or phenyl. For the Contracting State : AT 1. A herbicidal and plant-growth-regulating composition, characterized in that it contains as active ingredient an O-(pyridyloxy-phenyl)-lactic acid ester of the formula I  see diagramm : EP0008624,P20,F1  in which "Hal" is a halogen atom, X is hydrogen or a halogen atom, Y is an oxygen or sulfur atom, Z is a C1 -C4 -alkylene group which is unsubstituted or substituted by methyl, ethyl, cyano, methylcarbonyl or by a group -COQ, Q is a group -OR1 , -SR2  or -NR3 R4 , wherein R1  and R2  independently of one another are each hydrogen or the cation equivalent of a base 1/n M**n(cation), wherein M is an n-valent alkali metal cation or alkaline earth metal cation, or an Fe, Cu, Zn, Mn or Ni cation, or an ammonium group  see diagramm : EP0008624,P20,F2  n as an integer 1, 2 or 3 corresponds to the valency of the cation, whilst Ra , Rb , Rc and Rd  independently of one another were each hydrogen, benzyl, or a C1 -C4 -alkyl group which is unsubstituted or substituted by -OH, -NH2  or C1 -C4 -alkoxy ; or R1  and R2  independently of one another are each C1 -C18 -alkyl group which is unsubstituted or is substituted by halogen, nitro, cyano, C1 -C8 -alkoxy, C2 -C8 -alkoxy-alkoxy, C3 -C6 -alkenyloxy, C1 -C8 -alkylthio, C2 -C8 -alkanoyl, C2 -C8 -acyloxy, C2 -C8 -alkoxycarbonyl, carbamoyl, bis-(C1 -C4 -alkyl)-amino, tris-(C1 -C4 -alkyl)-ammonium, C3 -C8 -cycloalkenyl, or by a phenyl, phenoxy or 5-6-membered heterocyclic radical having 1 to 3 hetero atoms, each of which is unsubstituted or for its part is mono- or polysubstituted by halogen, C1 -C4 -alkyl or C1 -C4 -alkoxy ; or they are each a C3 -C18 -alkenyl group which is unsubstituted or is mono- or tetrasubstituted by halogen or is mono- substituted by phenyl or methoxycarbonyl ; or they are a C3 -C8 -alkynyl group ; or a C3 -C12 -cycloalkyl group which is unsubstituted or is substituted by halogen or C1 -C4 -alkyl ; or they are each a C3 -C8 -cycloalkenyl group ; or a phenyl group which is unsubstituted or is mono- or polysubstituted by halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, NO2 , CF3 , COOH, CN, OH, SO3 H, NH2  or -NH(C1 -C4 -alkyl) or -N(C1 -C4 -alkyl)2  ; or R1  and R2  are each a 5- to 6-membered heterocyclic ring having 1 to 3 hetero atoms, and R3  and R4  independently of one another are each hydrogen, or C1 -C4 -alkyl which is unsubstituted or is substituted by chlorine, cyano, hydroxyl or C1 -C4 -alkoxy, or they are each C3 -C4 -alkenyl and R3  is also C3 -C4 -alkynyl, C1 -C4 -alkoxy, phenyl or benzyl, or R3  and R4  together with the nitrogen atom to which they are attached also form a 5-6-membered heterocycle which can contain oxygen, sulfur or a group  see diagramm : EP0008624,P21,F3 wherein R5  is hydrogen, C1 -C4 -alkyl or phenyl, together with a carrier and other inert ingredients.