[DE] SUBSTITUIERTE 2-BENZ(O)YLPYRIDIN DERIVATE, DEREN HERSTELLUNG UND DEREN VERWENDUNG ALS HERBIZIDE<br/>[EN] SUBSTITUTED 2-BENZ(O)YLPYRIDINES, THEIR PREPARATION AND THEIR USE AS HERBICIDES<br/>[FR] DERIVES DE 2-BENZ(O)YLPYRIDINES SUBSTITUEES, LEUR PREPARATION ET LEUR UTILISATION COMME HERBICIDES
申请人:BASF AKTIENGESELLSCHAFT
公开号:WO1998042671A1
公开(公告)日:1998-10-01
(DE) Substituierte 2-Benz(o)ylpyridine der Formel (I) und deren Salze, wobei 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-Halogenalkyl, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl; R2 = H, Halogen; R3 = H, NO2, OH, Halogen, C1-C4-Alkoxy; R4 = H, NO2, OH, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy; R5 = H, NO2, CN, Halogen, C1-C8-Alkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, C3-C8-Cycloalkyl, C1-C8-Halogenalkyl, C2-C8-Halogenalkenyl, C2-C8-Halogenalkinyl, 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, gegebenenfalls substituiertes OH, SH, SO-H, -SO2-H, COOH oder 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, geg. subst. CHO, -O-CHO oder -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), geg. subst. -CH2-CH(Halogen-COOH, -CH=C(Halogen)-COOH oder -CH=C(C1-C4-Alkyl)-COOH, geg. subst. -CH=N-OH oder -CH(-Y-R15, -Z-R15), (II) oder (III); R9, R10 = H, C1-C8-Alkyl, C3-C8-Cycloalkyl, C2-C8-Alkenyl, C3-C8-Alkinyl, C1-C8-Halogenalkyl, 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, gegebenenfalls substituiertes Phenyl oder Phenyl-C1-C4-alkyl, oder R9 + R10 zusammen = gegebenenfalls substituierte Tetramethylen-, Pentamethylen- oder Ethylenoxyethylenkette; Y, Z = O, S; R15 = C1-C8-Alkyl, C1-C8-Halogenalkyl, 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, gegebenenfalls substituiertes OH oder COOH; R7 = H, NO2, Halogen, gegebenenfalls substituiertes OH; ausgenommen diejenigen Verbindungen (I), bei denen X = CH2 und R5 = geg. subst. OH sowie R3, R7 = H oder R1 = Halogen sowie R3, R4, R6, R7 = H; Verwendung: als Herbizide; zur Desikkation/Defoliation von Pflanzen.(EN) 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.(FR) L'invention concerne des 2-benz(o)ylpyridines substituées de la formule (I) et leurs sels, formule dans laquelle n = 0, 1; X = CO, CH2, CH(alkyle C1-C4), CH-OH, CH-CN, CH-halogène, C(halogène)2, CH-CONH2, CH-CO-O-(alkyle C1-C4), CH-O-(alkyle C1-C4), C(CN)(alkyle C1-C4); R1 = halogène, halogénure d'alkyle C1-C4, alkylthio C1-C4, alkylsulfinyle C1-C4, alkylesulfonyle C1-C4; R2 = H, halogène; R3 = H, NO2, HO, halogène, alcoxy C1-C4; R4 = H, NO2, OH, halogène, alkyle C1-C4, halogénure d'alykle C1-C4, alcoxy C1-C4; R5 = H, NO2, CN, Halogène, alkyle C1-C8, alkényle C3-C8, alkinyle C3-C8, cycloalkyle C3-C8, halogénure d'alkyle C1-C8, halogénure d'alkényle C2-C8, halogénure d'alkinyle C2-C8, alcoxy C1-C4-alkyle C1-C4, alkényloxy C2-C4-alkyle C1-C4, alkinyloxy C2-C4-alkyle C1-C4, alkylthio C1-C4-alkyle C1-C4, alkylsulfinyle C1-C4-alkyle C1-C4, alkylesulfonyle C1-C4-alkyle C1-C4, cyano-alkyle C1-C8, cyano-alkényle C2-C8, cyano-alkinyle C3C8, OH éventuellement subst., SH, SO-H, SO2H, COOH ou NH-COOH, -SO2Cl, -N(R9, R10), -NH-SO2-(alkyle C1-C8), -N[-SO2-alkyle C1-C8)]2, N-(alkyle C1-C8) [-SO2-(alkyle C1-C8)], -SO2-N(R9, R10), -O-CO-NH-R9, CHO éventuel. subst., -O-CHO ou -NH-CHO, -NH-CO-NH-R9, -O-CS-NH2, -O-CS-N(alkyle C1-C8)2, -CO-N(R9, R10), -CS-N(R9, R10), -CO-NH-SO2(alkyle C1-C4), -CO-N(alkyle C1-C4)-SO2(alkyle C1-C4), hydroxycarbonyle-alkyle C1-C8, (alcoxy C1-C8)carbonyle-alkyle C1-C6, -CH2-CH(halogène)-CO-N(R9, R10), -CH2-CH(halogène)-CN, -CH2-CH(halogène)-CO-(alkyle C1-C4), -CH2-CH(halogène) éventuel. subst., -CH=C(halogène)-COOH ou -CH=C(alkyle C1-C4)-COOH, -CH=N-OH éventuel. susbt. ou -CH(-Y-R15, -Z-R15), (II) ou (III); R9, R10 = H, alkyle C1-C8, cycloalkyle C3-C8, alkényle C2-C8, alkinyle C3-C8, halogénure d'alkyle C3-C8, alcoxy C1-C4-alkyle C1-C4, alkylthio C1-C4-alkyle C1-C4, alkylesulfinyle C1-C4-alkyle C1-C4, alkylesulfonyle C1-C4-akyle C1-C4, cyano-alkyle C1-C8, hydroxycarbonyle-alkyle C1-C4, (alcoxy C1-C4)carbonyle-alkyle C1-C4, (cycloalcoxy C3-C6)carbonyle-alkyle C1-C4, (alcoxy C1-C4)carbonyle-cycloalkyle C3-C7), alcoxy C1-C4-(alcoxy C1-C4)carbonyle-alkyle C1-C4, alcoxy C1-C6, phényle éventuellement substitué ou phényle-alkyle C1-C4, ou R9 + R10 conjointement = chaîne tétraméthylène, pentaméthylène ou éthalène-oxyéthylène éventuellement substituée; Y, Z = O, S; R15 = alkyle C1-C8, halogénure d'alkyle C1-C8, alcoxy C1-C4-alkyle C1-C4; R16 - R21 = H, CN, alkyle C1-C8, alcoxy C1-C4-alkyle C1-C4, alcoxy C1-C8, alcoxy C1-C4-alcoxy C1-C4, COOH, (alcoxy C1-C8)carbonyle, CONH2, (alkyle C1-C8)aminocarbonyle, di(alkyle C1-C8)aminocarbonyle; R6 = H, NO2, halogène, OH éventuellement substitué ou COOH; R7 = H, NO2, halogène, OH éventuellement substitué; à l'exception des composés (I) où X = CH2 et - R5 = OH éventuel. subst., ainsi que R3, R7 = H ou - R1 = halogène, ainsi que R3, R4, R6, R7 = H. Ces composés s'utilisent comme herbicides, ainsi que pour la dessiccation/défoliation de plantes.
Les substitués 2-benzo pyridines de la formula (I) et leurs acides salts, où 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-alkylsulfinyl, C1-C4-alkylesulfonyle, 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-C4-alkyl, C3-C8-alkenyl, C3-C8-alkinyl, C3-C8-cycloalkyl, C1-C8-halogen alkyl, C2-C8-halogen alkene, C2-C8-halogen alkyl, 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-alkylesulfonyle-C1-C4-alkyl, cyano-C1-C8-alkyl, cyano-C2-C8-alkenyl, cyano-C3-C8-alkinyl, OH ousubst. SH, SO-H, -SO2-H, COOH ou 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, élément experiments. CHO ousubst. -O-CHO ou -NH-CHO, NH-CO-NH-R9, -O-CS-NH2, -O-CS-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), -CH2-CH(halogen)-COON, -CH2-CH-halogen-COOH ou ), -CH=N-OH ousubst. -CH(-Y-R15, -Z-R15), (II) ou (III); R9, R10 = H, C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-alkinyl, C1-C8-halogen alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkyle sulfonyle-C1-C4-alkyl, C1-C4-alkynesulfenyl-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-exalkoxy)-carbonyl-C1-C4-alkyl, C1-C6-alkoxy, optionnellement substitué phényle ou phényle-alkyl C1-C4, ou R9 + R10 ensemble = optionnellement substitué tétraméthylène, pentaméthylène ou éthylène-oxyéthylène; Y, Z = O, S; R15 = C1-C8-alkyl, C1-C8-halogen alkyl, C1-C4-alkoxy-C1-C4-alkyl; R16 à 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, OH ou substitution. COOH; R7 = H, NO₂, halogen, OH ou substitution; à l'exception des composés (I) où X = CH₂ et R5 = OH ou substitution. ainsi que R3, R7 = H ou R1 = halogen, ainsi que R3, R4, R6, R7 = H. Ces composés sont utilisés comme acides herbicides et pour la dessication/ défoliation des plantes.