Novel 1-aryl-4-thiouracils

Details Novel 1-aryl-4-thiouracils Novel 1-aryl-4-thiouracils

C - Chemistry, Metallurgy

07

D

C07D 239/56 (2006.01) A01N 43/54 (2006.01) C07D 239/58 (2006.01) C07D 401/04 (2006.01) C07D 413/04 (2006.01)

Patent

CA 2349386

The invention relates to novel 1-aryl-4-thiouracils of formula (I), to their salts/enolethers used as herbicides, whereby R1 = H, NH2, C1-C6-alkyl; R2 = H, halogen, C1-C4-alkyl, C1-C4-alkyl halide; R3 = H, halogen, C1-C6-alkyl, methyl halide; R4 = H, halogen; R5 = CN, halogen, -CO-NH2, -CS-NH2, -OC(R8,R9)-CO- O(C1-C6-alkyl); Y = N, CH, or together with R6, a bridge ~C-O-C(R10)=N-; R6, together with R5, = a radical -N(R7)-C(O/S)-C(R8',R9')-O- bound to R5 via the oxygen, or 1) H, OH, SH, CN, NO2, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1- C6-alkoxy halide, C1-C6-alkylthio halide, C1-C6-alkylthio-(C1-C6- alkyl)carbonyl, (C1-C6-alkyl)imino-oxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1- C6-alkoxyamino-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl, 2) optionally substituted C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6- cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, C2-C6- alkynylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6- alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkynyl)carbonylthio, C1-C6- alkylsulfonyloxy or C1-C6-alkylsulfonyl, 3) 28 additional radicals; R7 = H, optionally substituted C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6- alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl or C3-C6- cycloalkoxy; R8, R9, R8', R9' = H, CN, C1-C6-alkyl; R10 = H, halogen, optionally substituted C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6- alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl or C3-C6- cycloalkoxy.

L'invention concerne de nouveaux 1-aryl-4-thiouraciles de formule (I), leur sels/énoléther, servant d'herbicides. Dans la formule, R?1¿ = H, NH¿2?, alkyle C¿1?-C¿6?; R?2¿ = H, halogène, alkyle C¿1?-C¿4?, halogénure d'alkyle C¿1?-C¿4?; R?3¿ = H, halogène, alkyle C¿1?-C¿6?, halogénure de méthyle; R?4¿ = H, halogène; R?5¿ = CN, halogène, -CO-NH¿2?, -CS-NH¿2?, -OC(R?8¿,R?9¿)-CO-O(alkyle C¿1?-C¿6?); Y = N, CH ou conjointement avec R?6¿ représentent un pont ~C-O-C(R?10¿)=N-; R?6¿ conjointement avec R?5¿ = un radical -N(R?7¿)-C(O/S)-C(R?8'¿,R?9'¿)-O- lié à R?5¿ par l'intermédiaire de l'oxygène, ou 1) H, OH, SH, CN, NO¿2?, halogène, alkyle C¿1?-C¿6?, halogénure d'alkyle C¿1?-C¿6?, halogénure d'alcoxy C¿1?-C¿6?, halogénure d'alkylthio C¿1?-C¿6?, alkylthio C¿1?-C¿6?(C¿1?-C¿6?-alkyl)carbonyle, (alkyl C¿1?-C¿6?)imino-oxycarbonyle, alcoxy C¿1?-C¿6? alkyle C¿1?-C¿6?, alcoxyamino C¿1?-C¿6? alkyle C¿1?-C¿6?, alcoxy C¿1?-C¿6? alkylamino C¿1?-C¿6? alkyle C¿1?-C¿6?, 2) l'un des radicaux suivants éventuellement substitués: alcoxy C¿1?-C¿6?, alkylthio C¿1?-C¿6?, cycloalcoxy C¿3?-C¿6?, cycloalkylthio C¿3?-C¿6?, alcényloxy C¿2?-C¿6?, alcénylthio C¿2?-C¿6?, alcynyloxy C¿2?-C¿6?, alcynylthio C¿2?-C¿6?, (alkyl C¿1?-C¿6?)carbonyloxy, (alkyl C¿1?-C¿6?)carbonylthio, (alcoxy C¿1?-C¿6?)carbonyloxy, (alcényl C¿2?-C¿6?)carbonyloxy, (alcényl C¿2?-C¿6?)carbonylthio, (alcynyl C¿2?-C¿6?)carbonyloxy, (alcynyl C¿2?-C¿6?)carbonylthio, alkyl C¿1?-C¿6? sulfonyloxy ou alkyl C¿1?-C¿6? sulfonyl, 3) 28 autres radicaux; R?7¿ = H, l'un des radicaux suivants éventuellement substitués: alkyle C¿1?-C¿6?, alcényl C¿3?-C¿6?, alcynyl C¿3?-C¿6?, alcoxy C¿1?-C¿6?, alcényl C¿3?-C¿6? oxy, alcynyl C¿3?-C¿6? oxy, cycloalkyle C¿3?-C¿6? ou cycloalcoxy C¿3?-C¿6?; R?8¿, R?9¿, R?8'¿, R?9'¿ = H, CN, alkyle C¿1?-C¿6?; R?10¿ = H, halogène, l'un des radicaux suivants éventuellement substitués : alkyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcynyle C¿3?-C¿6?, alcoxy C¿1?-C¿6?, alcényloxy C¿3?-C¿6?, alcynyloxy C¿3?-C¿6?, cycloalkyle C¿3?-C¿6? ou cycloalcoxy C¿3?-C¿6?.

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