Substituted aminotriazines having at least two...

C - Chemistry – Metallurgy – 07 – D

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C07D 251/18 (2006.01) A01N 43/68 (2006.01) C07D 251/48 (2006.01) C07D 405/12 (2006.01) C07D 409/12 (2006.01)

Patent

CA 2322417

The invention relates to substituted, optically active aminotriazines having at least two asymmetrically substituted carbon atoms of formula (I), in which A represents a single bond or each straight chained or branched alkandiyl or oxaalkandiyl; R1 represents amino, formylamino, or each alkylamino, dialkylamino, alkyl carbonyl amino, N-alkyl-N-alkyl carbonyl-amino, alkoxycarbonyl amino, N-alkyl-N-alkoxycarbonyl-amino, alkyl-aminoalkylide amino or dialkylamino alkylide amino which are optionally substituted by cyano, halogen or C1-C4-alkoxy; R2, R3 represent hydrogen, halogen or alkyl which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or R3 together with R2 represent alkandiyl which is optionally substituted by cyano, halogen, or C1-C4-alkyl; R4 represents alkyl or cycloalkyl; Y represents hydrogen, hydroxy, mercapto, amino, cyano, halogen or each alkyl, alkoxy, alkyl carbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, dialkylamino carbonyloxy, alkylthio, alkylamino or dialkylamino which are optionally substituted by cyano, halogen or C1-C4-alkoxy, and; Z represents a monocyclic or bicyclic carbocyclic or heterocyclic radicals which are optionally substituted. The substituents are provided with the provision that R2, R3 and Y are different from one another in each individual case, and that the substituents are bound on both carbon atoms, on which R2 and R3 or R4. R,R or R,S or S,R or S,S or R,rac or S,rac are configured [the first statement refers to the triazine-substituents -CR2R3Y, and the second statement refers to the amino-substituents -CHR4(A-Z)]. The invention also relates to a method for producing the compounds of formula (I) and to the utilization thereof as herbicides.

L'invention concerne des aminotriazines substituées optiquement actives, comportant au moins deux atomes de carbone à substitution asymétrique, de formule (I), dans laquelle A représente une liaison simple ou bien respectivement alcanediyle ou oxa-alcanediyle linéaire ou ramifié; R?1¿ représente amino, formylamino ou l'un des radicaux suivants éventuellement substitués par cyano, halogène ou alcoxy C¿1?-C¿4?: alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonylamino, alcoxycarbonylamino, N-alkyl-N-alcoxycarbonylamino, alkylaminoalkylidènamino ou dialkylaminoalkylidènamino; R?2¿, R?3¿ représentent hydrogène, halogène ou alkyle éventuellement substitué par cyano, halogène ou alcoxy C¿1?-C¿4?, ou R?3¿ représente conjointement avec R?2¿ alcanediyle éventuellement substitué par cyano, halogène ou alkyle C¿1?-C¿4?; R?4¿ représente alkyle ou cycloalkyle; Y représente hydrogène, hydroxy, mercapto, amino, cyano, halogène ou l'un des radicaux suivants éventuellement substitués par cyano, halogène ou alcoxy C¿1?-C¿4?: alkyle, alcoxy, alkylcarbonyloxy, alcoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylthio, alkylamino ou dialkylamino; et Z représente des radicaux monocycliques ou bicycliques, carbocycliques ou hétérocycliques, éventuellement substitués, et à condition que, dans chaque cas d'espèce, R?2¿, R?3¿ et Y soient différents les uns des autres, et que les substituants sur les deux atomes de carbone auxquels sont liés R?2¿ et R?3¿ ou R?4¿, soient configurés comme suit: R,R ou R,S ou S,R ou S,S ou R,rac ou S,rac [la première indication se rapporte aux substituants triazine -CR?2¿R?3¿Y et la deuxième aux substituants amino CHR?4¿(A-Z)]. L'invention concerne également un procédé pour la préparation des composés de formule (I) et leur utilisation comme herbicides.

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