3-aryluracils and intermediates for their preparation

C - Chemistry – Metallurgy – 07 – D

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C07D 413/04 (2006.01) A01N 43/60 (2006.01) A01N 43/64 (2006.01) A01N 43/72 (2006.01) A01N 43/84 (2006.01) C07D 239/54 (2006.01) C07D 239/56 (2006.01) C07D 241/44 (2006.01) C07D 241/52 (2006.01) C07D 241/54 (2006.01) C07D 265/36 (2006.01) C07D 401/14 (2006.01) C07D 403/04 (2006.01) C07D 403/14 (2006.01) C07D 405/14 (2006.01) C07D 409/14 (2006.01) C07D 413/14 (2006.01) C07D 417/14 (2006.01)

Patent

CA 2213717

3-Aryluracils (I) and their salts (with A = hydrogen) where: A = H, CH3, NH2; R1 = H, halogen; R2 = H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkylthio, C1-C6-alkylsulfenyl or C1-C6-alkylsulfonyl; R3 = H, halogen, C1-C6- alkyl; X = oxygen or -N(R7)-, with R7 = C1-C6-alkyl, C3-C6-alkenyl, C3-C6- alkynyl, C1-C6-alkylcarbonyl or C1-C6-alkoxy-C1-C6-alkyl; Y1 and Y2 = oxygen or sulfur; Z = oxygen or -N(R8)-; R5, R6 and R8 = H, C1-C6-alkyl, C3-C6- alkenyl, C3-C6-alkynyl or C1-C6-alkoxy-C1-C6-alkyl; or R6 and R8 together are a second chemical bond; R4 = H, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6- haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C3-C6-alkenyl- carbonyl, C3-C6-alkynylcarbonyl or C1-C6-alkylsulfonyl, where each of the last- mentioned 9 radicals can carry 1-3 substituents: R9 = H, C1-C6-alkyl, C3-C8- cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6- alkoxy)carbonyl-C1-C6-alkyl, unsubst. or subst. phenyl or phenyl-C1-C6-alkyl; R10 = H, OH, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1- C6-alkoxycarbonyl-C1-C6-alkoxy; R11 = C1-C6alkoxy, C3-C6-alkenyloxy, C1-C6- alkoxycarbonyl-C1-C6alkoxy; R12 = C1-C6-alkyl, C3-C6-alkenyl, C1-C6- alkoxycarbonyl-C1-C6-alkyl. Use: as herbicides; for the desiccation/defoliation of plants.

3-aryluraciles de formule (I) et leurs sels (A étant hydrogène). Dans ladite formule, A est H, CH¿3?, NH¿2?; R?1¿ est H, halogène; R?2¿ est H, halogène, alkyle C¿1?-C¿6?, haloalkyle C¿1?-C¿6?, alkylthio C¿1?-C¿6?, alkylesulfényle C¿1?-C¿6? ou alkylsulfonyle C¿1?-C¿6?; R?3¿ est H, halogène, alkyle C¿1?-C¿6?; X est oxygène ou -N(R?7¿)-, R¿7? étant alkyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcynyle C¿3?-C¿6?, alkylcarbonyle C¿1?-C¿6? ou alcoxy-C¿1?-C¿6?-alkyle-C¿1?-C¿6?; Y?1¿ et Y?2¿ sont oxygène ou soufre; Z est oxygène ou -N(R?8¿)-; R?5¿, R?6¿ et R?8¿ sont H, alkyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcynyle C¿3?-C¿6? ou alcoxy-C¿1?-C¿6?-alkyle-C¿1?-C¿6?; ou R?6¿ et R?8¿ ensemble sont une seconde liaison chimique; R?4¿ est H, alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿8?, haloalkyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcynyle C¿1?-C¿6?, alkylcarbonyle C¿1?-C¿6?, alcénylecarbonyle C¿3?-C¿6?, alcynylcarbonyle C¿3?-C¿6? ou alkylsulfonyle C¿1?-C¿6?, chacun des 9 radicaux susmentionnés pouvant porter de 1 à 3 substituants; R?9¿ est H, alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿8?, alcényle C¿3?-C¿6?, alcynyle C¿3?-C¿6?, alcoxy-C¿1?-C¿6?-alkyle-C¿1?-C¿6?, (alcoxy C¿1?-C¿6?)carbonyle-alkyle C¿1?-C¿6?, phényle substitué ou non substitué ou phénylalkyle C¿1?-C¿6?; R?10¿ est H, OH, alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿8?, alcoxy C¿1?-C¿6?, alcényloxy C¿3?-C¿6?, alcoxycarbonyle-C¿1?-C¿6?-alcoxy-C¿1?-C¿6?; R?11¿ est alcoxy C¿1?-C¿6?, alcényloxy C¿3?-C¿6?, alcoxycarbonyle-C¿1?-C¿6?-alcoxy-C¿1?-C¿6?; R?12¿ est alkyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcoxycarbonyle-C¿1?-C¿6?-alkyle-C¿1?-C¿6?. On utilise ces composés comme herbicides, ainsi que pour la dessiccation ou la défoliation de végétaux.

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