Patent EP-0015005-A1 (EP)
Inventor: KOCH MANFRED DR
IPC: C07D277/64
Filed: 1980-02-22
Abstract: 1. Claims for the Contracting states : BE, CH, DE, FR, GB, IT, LU, NL, SE Compounds of the formula I  see diagramm : EP0015005,P13,F1 in which R is halogen, CF3 , NO2 , CN, NH2 , (C1 -C4 )alkyl, (C1 -C4 )alkoxy, (C1 -C4 )alkylthio, or phenoxy optionally mono-, di- or tri-substituted by halogen, CF3 , (C1 -C4 )alkyl, NO2 or -NH-CO-R2 n is zero, or an integer from 1 to 4, A is O, S, NH, or N-(C1 -C4 )alkyl, X is -CH2 - or -CH2 -CH2 , R1 is H or (C1 -C4 )alkyl, Z is a group of the formula  see diagramm : EP0015005,P13,F2   see diagramm : EP0015005,P13,F3   see diagramm : EP0015005,P13,F4   see diagramm : EP0015005,P13,F5   see diagramm : EP0015005,P13,F6  CN, -CH2 OH,  see diagramm : EP0015005,P13,F7  or -CH2 -O-SO2 -R10 , R3 is H, (C1 -C12 )alkyl optionally substituted by 1 to 6 halogen atoms, preferably F, Cl, Br, and/or by OH, (C1 -C6 )alkoxy, (C1 -C4 )alkylthio, (C1 -C6 )alkoxy-(C2 -C6 )alkoxy, halo(C1 -C2 )alkoxy, methoxyethoxy-ethoxy, (C1 -C4 )alkylamino, di(C1 -C4 )alkylamino, (C1 -C4 )alkoxycarbonyl, phenyl, oxiranyl and phenoxy which in turn is optionally mono- or disubstituted by halogen or (C1 -C4 )alkyl, (C5 -C6 )cycloalkyl or halo(C5 -C6 )cyclo-alkyl ; (C3 -C6 )alkenyl, halo(C3 -C6 )alkenyl, or (C5 -C6 )cycloalkenyl ; (C3 -C4 )alkinyl optionally being mono- or disubstituted by (C1 -C6 )alkyl, phenyl, halogen, or (C1 -C2 )alkoxy ; phenyl optionally mono-, di-, or trisubstituted by (C1 -C4 )alkyl, (C1 -C4 )alkoxy, halogen, NO2 , or CF3 ; furfuryl, tetrahydrofurfuryl, or a cation equivalent of an organic or inorganic base ; R4 is (C1 -C6 )alkyl optionally substituted by (C1 -C4 )alkoxy, halogen or phenyl which in turn may be mono-, di- or trisubstituted by (C1 -C4 )alkyl and halogen ; (C3 -C6 )alkenyl or phenyl which is optionally mono-, di- or trisubstituted by (C1 -C4 )alkyl and/or halogen ; R5 is H, (C1 -C6 )alkyl, hydroxy(C1 -C6 )alkyl, or (C5 -C6 )cycloalkyl ; R6 is H or CH3 ; R7 is H, CH3 or C2 H5 ; R8 is H, CH3 , C2 H5 , or phenyl ; R9 is (C1 -C6 )alkyl, (C1 -C6 )haloalkyl, C3 -, C5 -, or C6 -cycloalkyl, (C3 -C6 )alkenyl, phenyl, (C1 -C4 )-alkylphenyl, (C1 -C4 )alkoxyphenyl, halophenyl, trifluormethylphenyl, or nitrophenyl ; and R10 is (C1 -C4 )alkyl or phenyl which is optionally mono-, di-, or trisubstituted by halogen, CF3 , NO2 , or (C1 -C4 )alkyl. 1. Claims for the Contracting State : AT Herbicidal agents containing a compound of the formula I  see diagramm : EP0015005,P15,F3  in which R is halogen, CF3 , NO2 , CN, NH2 , (C1 -C4 )alkyl, (C1 -C4 )alkoxy, (C1 -C4 )alkylthio, or phenoxy optionally mono-, di- or tri-substituted by halogen, CF3 , (C1 -C4 )alkyl, NO2 or -NH-CO-R2 n is zero, or an integer from 1 to 4, A is O, S, NH, or N-(C1 -C4 )alkyl, X is -CH2 - or -CH2 -CH2 , R1 is H or (C1 -C4 )alkyl, Z is a group of the formula  see diagramm : EP0015005,P15,F4   see diagramm : EP0015005,P15,F5   see diagramm : EP0015005,P15,F6   see diagramm : EP0015005,P15,F7   see diagramm : EP0015005,P15,F8  CN, -CH2 OH,  see diagramm : EP0015005,P15,F9  or -CH2 -O-SO2 -R10 R3 is H, (C1 -C12 )alkyl optionally substituted by 1 to 6 halogen atoms, preferably F, Cl, Br, and/or by OH, (C1 -C6 )alkoxy, (C1 -C4 )alkylthio, (C1 -C6 )alkoxy-(C2 -C6 )alkoxy, halo(C1 -C2 )alkoxy, methoxyethoxy-ethoxy, (C1 -C4 )alkylamino, di(C1 -C4 )alkylamino, (C1 -C4 )alkoxycarbonyl, phenyl, oxiranyl and phenoxy which in turn is optionally mono- or disubstituted by halogen or (C1 -C4 )alkyl, (C5 -C6 )cycloalkyl or halo(C5 -C6 )cyclo-alkyl ; (C3 -C6 )alkenyl, halo(C3 -C6 )alkenyl, or (C5 -C6 )cycloalkenyl ; (C3 -C4 )alkinyl optionally being mono- or disubstituted by (C1 -C6 )alkyl, phenyl, halogen, or (C1 -C2 )alkoxy ; phenyl optionally mono-, di-, or trisubstituted by (C1 -C4 )alkyl, (C1 -C4 )alkoxy, halogen, NO2 , or CF3 ; furfuryl, tetrahydrofurfuryl, or a cation equivalent of an organic or inorganic base ; R4 is (C1 -C6 )alkyl optionally substituted by (C1 -C4 )alkoxy, halogen or phenyl which in turn may be mono-, di- or trisubstituted by (C1 -C4 )alkyl and halogen ; (C3 -C6 )alkenyl or phenyl which is optionally mono-, di- or trisubstituted by (C1 -C4 )alkyl and/or halogen ; R5 is H, (C1 -C6 )alkyl, hydroxy(C1 -C6 )alkyl, or (C5 -C6 )cycloalkyl ; R6 is H or CH3 ; R7 is H, CH3 or C2 H5 ; R8 is H, CH3 , C2 H5 , or phenyl ; R9 is (C1 -C6 )alkyl, (C1 -C6 )haloalkyl, C3 -, C5 -, or C6 -cycloalkyl, (C3 -C6 )alkenyl, phenyl, (C1 -C4 )-alkylphenyl, (C1 -C4 )alkoxyphenyl, halophenyl, trifluoromethylphenyl, or nitrophenyl ; and R10 is (C1 -C4 )alkyl or phenyl which is optionally mono-, di-, or trisubstituted by halogen, CF3 , NO2 , or (C1 -C4 )alkyl.