C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 213/61 (2006.01) A01N 43/40 (2006.01)
Patent
CA 2283981
Substituted 2-benz(o)ylpyridines of formula (I) and the salts thereof, wherein n = 0, 1; x = CO, CH2, CH(C1-C4-alkyl), CH-OH, CH-CN, CH-halogen, C(halogen)2, CH-CONH2, CH-CO-O(C1-C4-alkyl), CH-O(C1-C4-alkyl), C(CN) (C1-C4-alkyl); R1 = halogen, C1-C4-halogen alkane, C1-C4-alkylthio, C1-C4-alkyl sulfinyl, C1-C4- alkyl sulfonyl; R2 = H, halogen; R3 = H, NO2, OH, halogen, C1-C4-alkoxy; R4 = H, NO2, OH, halogen, C1-C4-alkyl, C1-C4 halogen alkane, C1-C4-alkoxy; R5 = H, NO2, CN, halogen, C1-C8-alkyl, C3-C8-alkenyl,C3-C8-alkinyl, C3-C8-cycloalkyl, C1-C8-halogen alkane, C2-C8-halogen alkenyl, C2-C8-halogen alkane, C1-C4- alkoxy-C1-C4-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C2-C4-alkinyloxy-C1-C4- alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4- alkylsulfonyl-C1-C4-alkyl, cyano-C1-C8-alkyl, cyano-C2-C8-alkenyl, cyano-C3-C8- alkinyl, optionally substituted OH, SH, SO-H, -SO2-H, COOH or NH-COOH, -SO2Cl, -N(R9, R10), -NH-SO2-(C1-C8-alkyl), -N[-SO2-(C1-C8-alkyl)]2, -N(C1-C8-alkyl) [- SO2-(C1-C8-alkyl)], -SO2-N(R9, R10), -O-CO-NH-R9, optionally substituted CHO, - O-CHO or -NH-CHO, NH-CO-NH-R9, -O-CS-NH2, -OCS-N(C1-C8-alkyl)2, -CO-N(R9, R10), -CS-N (R9, R10), -CO-NH-SO2-(C1-C4-alkyl), -CO-N(C1-C4-alkyl), -SO2-(C1- C4-alkyl), hydroxycarbonyl-C1-C8-alkyl, (C1-C8-alkoxy)carbonyl-C1-C6-alkyl, - CH2-CH(halogen)-CO-N(R9, R10), -CH2-CH(halogen)-CN, -CH2-CH(halogen)-CO-(C1-C4- alkyl), optionally substituted -CH2-CH(halogen-COOH, -CH=C(halogen)-COOH or - CH=C(C1-C4-alkyl)-COOH, optionally substituted -CH=N-OH or -CH(-Y-R15, -Z- R15), (II) or (III); R9, R10 = H, C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8- alkenyl, C3-C8-alkinyl, C1-C8-halogen alkane, C1-C4-alkoxy-C1-C4-alkyl, C1-C4- alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1- C4-alkyl, cyano-C1-C8-alkyl, hydroxycarbonyl-C1-C4-alkyl, (C1-C4- alkoxy)carbonyl-C1-C4-alkyl, (C3-C6-cycloalkoxy)carbonyl-C1-C4-alkyl, (C1-C4- alkoxy)carbonyl-C3-C7-cycloalkyl, C1-C4-alkoxy-(C1-C4)alkoxy)-carbonyl-C1-C4- alkyl, C1-C6-alkoxy, optionally substituted phenyl or phenyl-C1-C4-alkyl or R9 + R10 together = optionally substituted tetramethylene, pentamethylene or ethylene oxyethylene chain; Y, Z = O, S; R15 = C1-C8-alkyl, C1-C8 halogen alkane, C1-C4-alkoxy-C1-C4-alkyl; R16-R21 = H, CN, C1-C8-alkyl, C1-C4-alkoxy- C1-C4-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy, COOH, (C1-C8- alkoxy)carbonyl, CONH2, (C1-C8-alkyl)aminocarbonyl, di(C1-C8- alkyl)aminocarbonyl; R6 = H, NO2, halogen, optionally substituted OH or COOH; R7 = H, NO2, halogen, optionally substituted OH; excluding those compounds in (I) in wherein X = CH2 and R5 = optionally substituted OH as well as R3, R7 = H or R1 = halogen as well as R3, R4, R6, R7 = H. The invention further relates to the use of said substances as herbicides and for dessication/defoliation of plants.
L'invention concerne des 2-benz(o)ylpyridines substituées de la formule (I) et leurs sels, formule dans laquelle n = 0, 1; X = CO, CH¿2?, CH(alkyle C¿1?-C¿4?), CH-OH, CH-CN, CH-halogène, C(halogène)¿2?, CH-CONH¿2?, CH-CO-O-(alkyle C¿1?-C¿4?), CH-O-(alkyle C¿1?-C¿4?), C(CN)(alkyle C¿1?-C¿4?); R?1¿ = halogène, halogénure d'alkyle C¿1?-C¿4?, alkylthio C¿1?-C¿4?, alkylsulfinyle C¿1?-C¿4?, alkylesulfonyle C¿1?-C¿4?; R?2¿ = H, halogène; R?3¿ = H, NO¿2?, HO, halogène, alcoxy C¿1?-C¿4?; R?4¿ = H, NO¿2?, OH, halogène, alkyle C¿1?-C¿4?, halogénure d'alykle C¿1?-C¿4?, alcoxy C¿1?-C¿4?; R?5¿ = H, NO¿2?, CN, Halogène, alkyle C¿1?-C¿8?, alkényle C¿3?-C¿8?, alkinyle C¿3?-C¿8?, cycloalkyle C¿3?-C¿8?, halogénure d'alkyle C¿1?-C¿8?, halogénure d'alkényle C¿2?-C¿8?, halogénure d'alkinyle C¿2?-C¿8?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkényloxy C¿2?-C¿4?-alkyle C¿1?-C¿4?, alkinyloxy C¿2?-C¿4?-alkyle C¿1?-C¿4?, alkylthio C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkylsulfinyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkylesulfonyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, cyano-alkyle C¿1?-C¿8?, cyano-alkényle C¿2?-C¿8?, cyano-alkinyle C¿3?C¿8?, OH éventuellement subst., SH, SO-H, SO¿2?H, COOH ou NH-COOH, -SO¿2?Cl, -N(R?9¿, R?10¿), -NH-SO¿2?-(alkyle C¿1?-C¿8?), -N[-SO¿2?-alkyle C¿1?-C¿8?)]¿2?, N-(alkyle C¿1?-C¿8?) [-SO¿2?-(alkyle C¿1?-C¿8?)], -SO¿2?-N(R?9¿, R?10¿), -O-CO-NH-R?9¿, CHO éventuel. subst., -O-CHO ou -NH-CHO, -NH-CO-NH-R?9¿, -O-CS-NH¿2?, -O-CS-N(alkyle C¿1?-C¿8?)¿2?, -CO-N(R?9¿, R?10¿), -CS-N(R?9¿, R?10¿), -CO-NH-SO¿2?(alkyle C¿1?-C¿4?), -CO-N(alkyle C¿1?-C¿4?)-SO¿2?(alkyle C¿1?-C¿4?), hydroxycarbonyle-alkyle C¿1?-C¿8?, (alcoxy C¿1?-C¿8?)carbonyle-alkyle C¿1?-C¿6?, -CH¿2?-CH(halogène)-CO-N(R?9¿, R?10¿), -CH¿2?-CH(halogène)-CN, -CH¿2?-CH(halogène)-CO-(alkyle C¿1?-C¿4?), -CH¿2?-CH(halogène) éventuel. subst., -CH=C(halogène)-COOH ou -CH=C(alkyle C¿1?-C¿4?)-COOH, -CH=N-OH éventuel. susbt. ou -CH(-Y-R?15¿, -Z-R?15¿), (II) ou (III); R?9¿, R?10¿ = H, alkyle C¿1?-C¿8?, cycloalkyle C¿3?-C¿8?, alkényle C¿2?-C¿8?, alkinyle C¿3?-C¿8?, halogénure d'alkyle C¿3?-C¿8?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkylthio C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkylesulfinyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkylesulfonyle C¿1?-C¿4?-akyle C¿1?-C¿4?, cyano-alkyle C¿1?-C¿8?, hydroxycarbonyle-alkyle C¿1?-C¿4?, (alcoxy C¿1?-C¿4?)carbonyle-alkyle C¿1?-C¿4?, (cycloalcoxy C¿3?-C¿6?)carbonyle-alkyle C¿1?-C¿4?, (alcoxy C¿1?-C¿4?)carbonyle-cycloalkyle C¿3?-C¿7?), alcoxy C¿1?-C¿4?-(alcoxy C¿1?-C¿4?)carbonyle-alkyle C¿1?-C¿4?, alcoxy C¿1?-C¿6?, phényle éventuellement substitué ou phényle-alkyle C¿1?-C¿4?, ou R?9¿ + R?10¿ conjointement = chaîne tétraméthylène, pentaméthylène ou éthalène-oxyéthylène éventuellement substituée; Y, Z = O, S; R?15¿ = alkyle C¿1?-C¿8?, halogénure d'alkyle C¿1?-C¿8?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?; R?16¿ - R?21¿ = H, CN, alkyle C¿1?-C¿8?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, alcoxy C¿1?-C¿8?, alcoxy C¿1?-C¿4?-alcoxy C¿1?-C¿4?, COOH, (alcoxy C¿1?-C¿8?)carbonyle, CONH¿2?, (alkyle C¿1?-C¿8?)aminocarbonyle, di(alkyle C¿1?-C¿8?)aminocarbonyle; R?6¿ = H, NO¿2?, halogène, OH éventuellement substitué ou COOH; R?7¿ = H, NO¿2?, halogène, OH éventuellement substitué; à l'exception des composés (I) où X = CH¿2? et - R?5¿ = OH éventuel. subst., ainsi que R?3¿, R?7¿ = H ou - R?1¿ = halogène, ainsi que R?3¿, R?4¿, R?6¿, R?7¿ = H. Ces composés s'utilisent comme herbicides, ainsi que pour la dessiccation/défoliation de plantes.
Hamprecht Gerhard
Menges Markus
Menke Olaf
Misslitz Ulf
Rack Michael
Basf Aktiengesellschaft
Robic
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