1-sulfonyl-3-phenylpyrazoles and their use as herbicides and...

Details 1-sulfonyl-3-phenylpyrazoles and their use as herbicides and... 1-sulfonyl-3-phenylpyrazoles and their use as herbicides and...

C - Chemistry, Metallurgy

07

D

C07D 231/12 (2006.01) A01N 43/56 (2006.01) C07D 231/16 (2006.01) C07D 231/18 (2006.01) C07D 231/24 (2006.01)

Patent

CA 2266392

1-sulfonyl-3-phenylpyrazoles having the formula (I) and their salts are disclosed. In the formula, R1 is C1-C4-alkyl, C1-C4-alkyl halide; R2 is C1-C4- alkyl, C1-C4-alkyl halide; R3 is H, CN, halogen, C1-C4-alkyl; R4 is H, halogen; R5 is H, CN, NO2, halogen, C1-C4-alkyl, C1-C4-alkyl halide, C1-C4- alkoxy, C1-C4-alkoxy halide; X is a chemical bond, an optionally substituted methylene, ethylene, propan-1,3-diyl, ethen-1,2-diyl chain or an oxymethylene or thiamethylene chain bound to the phenyl ring by the heteroatom; R6 is H, NO2, CN, halogen, SO2-halogen, -O-Y-R8, -O-CO-Y-R8, -N(Y-R8)(Z-R9), -N(Y-R8)- SO2-Z-R9, -N(SO2-Y-R8)(SO2-Z-R9), -N(Y-R8)-CO-Z-R9, -N(Y-R8)(O-Z-R9), -S-Y-R8, -SO-Z-R8, -SO2-Y-R8, -SO2-O-Y-R8, -SO2-N(Y-R8)(Z-R9), -CO-Y-R8, -C(=NOR10)-Y- R8, -(=NOR10)-O-Y-R8, -CO-O-Y-R8, -CO-S-Y-R8, -CO-N(Y-R8)(Z-R9), -CO-N(Y-R8)(O- Z-R9), -PO(O-Y-R8)2; R7 is H, or R5 + XR6 or XR6 + R7 form, together with the C atoms of the phenyl ring which interconnect them, an annulated, optionally substituted carbocyclic or 5-/6-membered heterocyclic ring with 1-3 heteroatoms, whereas the cycle may also contain 1 or 2 CO-, CS- or SO2 ring members. These compounds are useful as herbicides, and for desiccating/defoliating plants.

L'invention concerne des 1-sulfonyl-3-phénylpyrazoles de formule (I) et leurs sels. Dans cette formule, R?1¿ est alkyle C¿1?-C¿4?, halogénure d'alkyle C¿1?-C¿4?; R?2¿ est alkyle C¿1?-C¿4?, halogénure d'alkyle C¿1?-C¿4?; R?3¿ est H, CN, halogène, alkyle C¿1?-C¿4?; R?4¿ est H, halogène; R?5¿ est H, CN, NO¿2?, halogène, alkyle C¿1?-C¿4?, halogénure d'alkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?, halogénure d'alcoxy C¿1?-C¿4?; X représente une liaison chimique, une chaîne méthylène, éthylène, propan-1,3-diyle, éthèn-1,2-diyle éventuellement substituée ou bien une chaîne oxyméthylène ou thiaméthylène liée au cycle phénylique par l'hétéroatome; R?6¿ est H, NO¿2?, CN, halogène, SO¿2?-halogène, -O-Y-R?8¿, -O-CO-Y-R?8¿, -N(Y-R?8¿)(Z-R?9¿), -N(Y-R?8¿)-SO¿2?-Z-R?9¿, -N(SO¿2?-Y-R?8¿)(SO¿2?-Z-R?9¿), -N(Y-R?8¿)-CO-Z-R?9¿, -N(Y-R?8¿)(O-Z-R?9¿), -S-Y-R?8¿, -SO-Z-R?8¿, -SO¿2?-Y-R?8¿, -SO¿2?-O-Y-R?8¿, -SO¿2?-N(Y-R?8¿)(Z-R?9¿), -CO-Y-R?8¿, -C(=NOR?10¿)-Y-R?8¿, -(=NOR?10¿)-O-Y-R?8¿, -CO-O-Y-R?8¿, -CO-S-Y-R?8¿, -CO-N(Y-R?8¿)(Z-R?9¿), -CO-N(Y-R?8¿)(O-Z-R?9¿), -PO(O-Y-R?8¿)¿2?; R?7¿ est H, ou bien R?5¿ + XR?6¿ ou XR?6¿ + R?7¿ forment, conjointement avec les atomes de C du cycle phénylique qui les relient, un noyau carbocyclique ou hétérocyclique pentagonal ou hexagonal annelé, éventuellement substitué, avec un 1-3 hétéroatomes, le cycle pouvant également contenir 1 ou 2 chaînons cycliques CO-Cs- ou SO¿2?. Ces composés sont utiles comme herbicides, et pour le dessèchement/la défoliation de végétaux.

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