1-aryl-1,3-dihydro-imidazol-2-(thi)one derivatives,...

C - Chemistry – Metallurgy – 07 – D

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C07D 233/86 (2006.01) A01N 43/50 (2006.01) C07D 233/70 (2006.01) C07D 401/04 (2006.01) C07D 413/04 (2006.01)

Patent

CA 2387706

The invention relates to novel substituted 1-aryl-1,3-dihydro-imidazol-2- (thi)one of formula (I) and the salts of said compound whereby R1=NH2, C1-C6- alkyl, C1-C6-halogenalkyl; R2=OH, SH, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6- alkylthio, C1-C4-halogenalkylthio, C1-C6-alkylsulfinyl, C1-C4- halogenalkylsulfonyl, C1-C4-halogenalkyl or C1-C6-alkyl; R3=H, halogen, C1-C6- alkyl, halogenmethyl; R4=H, halogen; R5=CN, halogen, -CO-NH2, -CS-NH2, - OC(R8,R9)-CO-O(C1-C6-alkyl); Y=N, CH or in conjunction with R6 a bridge >C-O- C(R10)=N-, >C-S-C(R10)=N- or >C-N=C(R10)-O-; R6+R5= or a N(R7)-C(O/S)- C(R8',R9')-O- radical, bonded at the oxygen moiety to R5 or 1) OH, SH, CN, NO2, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-halogenalkoxy, C1-C6- halogenalkylthio, C1-C6-alkylthio-(C1-C6-alkyl)carbonyl, (C1-C6- alkyl)iminooxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxyamino-C1-C6- alkyl, C1-C6-alkoxy-C1-C6-alkoxyamino-C1-C6-alkyl, 2) optionally substit. C1- C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6- alkenyloxy, C2-C6-alkenylthio, C2-C6-alkinyloxy, C2-C6-alkinylthio, (C1-C6- alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6-alkoxy)carbonyloxy, (C2- C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6- alkinyl)carbonyloxy, (C2-C6-alkinyl)carbonylthio, C1-C6-alkylsulfonyloxy or C1- C6-alkylsulfonyl, 3) 28 other radicals; R7=H, optionally subst. C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6- alkinyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkyloxy; R8, R9, R8', R9' = H, CN, C1-C6-alkyl; R10=H, halogen, optionally subst. C1-C6-alkyl, C3-C6-alkenyl, C3- C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkyloxy. Use: as a herbicide or as a dessicating/defoliating agent for plants.

L'invention concerne des 1-aryle-1,3-dihydro-imidazole-(thi)ones de la formule (I) et leurs sels avec R?1¿ = NH¿2?, C¿1?-C¿6?-alkyle, C¿1?-C¿6?-halogénure d'alkyle; R?2¿ = OH, SH, C¿1?-C¿6?-alkoxy, C¿1?-C¿4?-alkylthio, C¿1?-C¿4?-halogénure d'alkylthio, C¿1?-C¿6?-alkylsulfinyle, C¿1?-C¿4?-halogénure d'alkylsulfinyle, C¿1?-C¿6?-alkylsulfonyle, C¿1?-C¿4?-halogénure d'alkylsulfonyle, C¿1?-C¿4?-halogénure d'alkyle ou C¿1?-C¿6?-alkyle; R?3¿ = H, halogène, C¿1?-C¿6?-alkyle, halogénure de méthyle; R?4¿ = H, halogène; R?5¿ = CN, halogène, -CO-NH¿2?, -CS-NH¿2?, -OC(R?8¿,R?9¿)-CO-O(C¿1?-C¿6?-alkyle); Y = N, CH, ou un pont avec R?6¿ >C-O-C(R?10¿)=N-, >C-S-C(R?10¿)=N-, ou >C-N=C(R?10¿)-O-; R?6¿+R?5¿ = est un reste lié à R?5¿ par l'oxygène -N(R?7¿)-(C(O/S)-C(R?8'¿, R?9'¿)-O-, ou 1) OH, SH, CN, NO¿2?, C¿1?-C¿6?-alkyle, C¿1?-C¿6?-halogénure d'alkyle, C¿1?-C¿6?-halogénure d'alkoxy, C¿1?-C¿6?-halogénure d'alkylthio, C¿1?-C¿6?-alkylthio-(C¿1?-C¿6?-alkyle)carbonyle, (C¿1?-C¿6?-alkyle)iminooxycarbonyle, C¿1?-C¿6?-alkoxy-C¿1?-C¿6?-alkyle, C¿1?-C¿6?-alkoxyamino-C¿1?-C¿6?-alkyle, C¿1?-C¿6?-alkoxy-C¿1?-C¿6?-alkylamino-C¿1?-C¿6?-alkyle, 2) éventuellement subst. C¿1?-C¿6?-alkoxy, C¿1?-C¿6?-alkylthio, C¿3?-C¿6?-cycloalkyloxy, C¿3?-C¿6?-cycloalkylthio, C¿2?-C¿6?-alcényloxy, C¿2?-C¿6?-alcénylthio, C¿2?-C¿6?-alkinyloxy, C¿2?-C¿6?-alkinylthio, (C¿1?-C¿6?-alkyle)carbonyloxy, (C¿1?-C¿6?-alkyle)carbonylthio, (C¿1?-C¿6?-alkoxy)carbonyloxy, (C¿2?-C¿6?-alcényle)carbonyloxy, (C¿2?-C¿6?-alcényle)carbonythio, (C¿2?-C¿6?-alkinyle)carbonyloxy, (C¿2?-C¿6?-alkinyle)carbonylthio, C¿1?-C¿6?-alkylsulfonyloxy, ou C¿1?-C¿6?-alkylsulfonyle, 3) 28 autres restes; R?7¿ = H, éventuellement subst. C¿1?-C¿6?-alkyle, C¿3?-C¿6?-alcényle, C¿3?-C¿6?-alkinyle, C¿1?-C¿6?-alkoxy, C¿3?-C¿6?-alcényloxy, C¿3?-C¿6?-alkinyloxy, C¿3?-C¿6?-cycloalkyle ou C¿3?-C¿6?-cycloalkyloxy; R?8¿, R?9¿, R?8'¿, R?9'¿ = H, CN, C¿1?-C¿6?-alkyle; R?10¿ = H, halogène, éventuellement subst. C¿1?-C¿6?-alkyle, C¿3?-C¿6?-alcényle, C¿3?-C¿6?-alkinyle, C¿1?-C¿6?-alkoxy, C¿3?-C¿6?-alcényloxy, C¿3?-C¿6?-alkinyloxy, C¿3?-C¿6?-cycloalkyle ou C¿3?-C¿6?-cycloalkyloxy. Ces composés peuvent être utilisés en tant qu'herbicides ou pour la dessiccation/défoliation de plantes.

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