Optically active substituted 2,4-diamino-1,3,5-triazines as...

C - Chemistry – Metallurgy – 07 – D

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C07D 251/18 (2006.01) A01N 43/68 (2006.01)

Patent

CA 2322482

The invention relates to novel optically active substituted 2,4-diamino-1,3,5- triazines of formula (I), wherein Ar represents optionally substituted aryl, aryl being a carbocyclical or heterocyclical, monocyclical or bicyclical aromatic grouping from the following series: phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents being selected from the following series: cyano, nitro, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4- alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-halogenalkylthio, C1-C4- alkylsulfinyl, C1-C4-halogenalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4- halogenalkylsulfonyl, C1-C4-alkylamino and C1-C4-alkoxy-carbonyl; R1 represents alkyl with 1 to 4 carbon atoms, R2 represents alkyl optionally substituted with hydroxy, cyano, halogen or C1-C4-alkoxy, with 1 to 4 carbon atoms, and R3 represents alkyl optionally substituted with cyano, halogen or C1-C4-alkoxy, with 2 to 4 carbon atoms, the substituents on the carbon atom to which R1 is bonded being arranged in R-configuration. The invention also relates to methods and novel intermediate products for producing the inventive substituted 2,4-diamino-1,3,5-triazines and to their use as herbicides.

L'invention concerne une nouvelle 2, 4-diamino-1,3,5-triazine substituée optiquement active de formule (I) où Ar représente aryle éventuellement substitué, aryle représentant un groupe aromatique carbocyclique ou hétérocyclique, monocyclique ou bicyclique de la série Phényle, naphthyle, pyridinyle, pyrimidinyle, furyle, benzofuryle, thiényle et benzothiényle et les substituants éventuels étant sélectionnés parmi cyano, nitro, carbamoyle, thiocarbamoyle, halogène, alkyle C¿1?-C¿4?, halogènalkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?, halogènalcoxy C¿1?-C¿4?, alkylthio C¿1?-C¿4?, halogènalkylthio C¿1?-C¿4?, alkylsulfinyle C¿1?-C¿4?, halogènalkylsulfinyle C¿1?-C¿4?, alkylsulfonyle C¿1?-C¿4?, halogènalkylsulfonyle C¿1?-C¿4?, alkylamino C¿1?-C¿4?, alcoxy-carbonyle C¿1?-C¿4?; R?1¿ représente alkyle avec 1 à 4 atomes de carbone; R?2¿ représente alkyle avec 1 à 4 atomes de carbone éventuellement substitué par hydroxy, cyano, halogène ou alcoxy C¿1?-C¿4? et R?3¿ représente alkyle avec 2 à 4 atomes de carbone éventuellement substitué par cyano, halogène ou alcoxy C¿1?-C¿4?, les substituants liés à l'atome de carbone auquel R?1¿ est lié, étant en configuration en R. L'invention concerne également un procédé et de nouveaux produits intermédiaires pour leur production et leur utilisation comme herbicides.

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