1-aryl-1,3,5-triazine-4-thione-2,6-diones, production...

C - Chemistry – Metallurgy – 07 – D

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C07D 251/38 (2006.01) A01N 43/64 (2006.01) A01N 43/76 (2006.01) A01N 53/00 (2006.01) C07D 413/04 (2006.01)

Patent

CA 2364660

The invention relates to novel 1-aryl-4-thiotriazines of formula (I), wherein R1 = H, NH2, C1-C4-alkyl, C1-C4-alkyl halide; R2 = H, NH2, C1-C4-alkyl, C1-C4- alkyl halide; R3 = H, halogen; R4 = CN, halogen; Y = nitrogen, the methine group or together with R5, a bridge ~C-O-C(R6)=N-; R5 = 1) hydrogen, hydroxy, mercapto, nitro, halogen, C1-C6-alkyl, C1-C6-alkyl halide, 2) C1-C6-alkoxy, C1- C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6- alkenylthio, C2-C6-alkinyloxy or C2-C6-alkinylthio, each of these 8 radicals optionally bearing one of the following substituents: halogen, cyano, -CO-R8, - CO-OR8 or -CO-N(R8)-R9; 3) -CO-R11, -C(R11)(OR13)(OR14), -C(R11)=C(R15)-CO- R16, -CH(R11)-CH(R15)-CO-R16, -CO-OR20, -C(R10)=N-OR7, -N(R21)-R22 or -CO- N(R21)-R22; and R6 = H, halogen, optionally substituted C1-C6-alkyl, C3-C6- alkenyl, C3-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3- C6-cycloalkyl or C3-C6-cycloalkoxy. The invention also relates to salts and enol ethers of the inventive compounds (I), to a method for producing them and to their use as herbicides.

Nouvelles 1-aryl-4-thiotriazines de formule (I) dans laquelle R?1¿ représente H, NH¿2?, alkyle C¿1?-C¿4?, halogénoalkyle C¿1?-C¿4?; R?2¿ représente H, NH¿2?, alkyle C¿1?-C¿4?, halogénoalkyle C¿1?-C¿4?; R?3¿ représente H, halogène; R?4¿ représente CN, halogène; Y représente azote, le groupe méthine ou, avec R?5¿, un pont ~C-O-C(R?6¿)=N-; R?5¿ représente (1) hydrogène, hydroxy, mercapto, nitro, halogène, alkyle C¿1?-C¿6?, halogénoalkyle C¿1?-C¿6?, (2) 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?, alcénylethio C¿2?-C¿6?, alcynyloxy C¿2?-C¿6? ou alcynylthio C¿2?-C¿6?, chacun de ces 8 restes pouvant porter, si nécessaire, l'un des substituants suivants: halogène, cyano, -CO-R?8¿, -CO-OR?8¿ ou -CO-N(R?8¿)-R?9¿, (3) -CO-R?11¿, -C(R?11¿)(OR?13¿)(OR?14¿), -C(R?11¿)=C(R?15¿)-CO-R?16¿, -CH(R?11¿)-CH(R?15¿)-CO-R?16¿, -CO-OR?20¿, -C(R?10¿)=N-OR?7¿, -N(R?21¿)-R?22¿ ou -CO-N(R?21¿)-R?22¿; R?6¿ représente H, halogène, 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? éventuellement substitués, ainsi que leurs sels et énoléthers, procédé de préparation des nouveaux composés de formule (I) et leur utilisation en tant qu'herbicides.

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