Patent TW-338038-B (TW)
Title: Fungicidal quinolines
Inventor: EBERHARD AMMERMANN
IPC: C07D401/12
Filed: 1996-09-04
Granted: 1998-08-11
Abstract: Quinolines of the formula (I): where the substituents having the following meanings: R1, R2, R3 and R4 in each case independently of one another are hydrogen, hydroxyl, nitro halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxyalkyl, R5, R6 in each case independently of one another are hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio; R7 is hydrogen, C1-C4-alkyl, formyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl; R8 is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkyny, or C1-C8-alkllcarbonyl, it being possible for these groups to be partially or fully halogenated, C3-C7-cycloalkyl or C3-C7-cycloalkenyl, it being possible for these radicals to be partially or fully halogenated, aryl or heteroaryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfoxy, C1-C4-alkylsulfonyloxy, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkoxycarbonyl, aryl, aryloxy; R7 and R8 together form a bond; R9 is aryl or hetaryl, it being possible for these radicals to have attached to them one to three of the following substituents: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylamino, di-C1-C4-alkylamino, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkoxycarbonyl, aryl, aryloxy; and te N-oxides and the acid addition salts of the quinolines of the formula I, with the exception of the compounds where the radicals are defined as follows: 1 a-d R1, 2, 3, 4, 5, 6, 7, 8 = H; R9=C6H5, 4-Cl-C6H4, 2, 4-di-Cl-C6H3, 2, 4-di-Br-C6-H3, 1 e-h R1, 2, 3, 4, 5, 6, 7, 8=H; R9=4-Cl-C6H4, 2, 4-di-Cl-C6H3, in each case in the form of the N-oxide and the HCl salt, 1 i R1, 2, 3, 4, 5, 6, 7, 8=H; R9=4-Br-C6H4 HBr salt 1 j-k R1, 2, 3, 4, 6, 8=H; R5=CH3; R7=H, CH3; R9=C6H5 1 m R1, 3, 4, 6, 7, 8=H; R2,5-CH3; R9=C6H5, 1 n R1, 3, 4, 5, 6, 7, 8=H; R2=CH3; R9=4-NO2-C6H4;HCl salt, N-oxide 1 r-s R1, 2, 4, 5, 6, 7, 8=H; R3=Cl; R9=4-NO2-C6H4, 4-Cl-C6H4 1 t-u R1, 2, 3, 4, 6, 7, 8=H; R5=Cl; R9=4-Cl-C6H4, 2, 4-di-Cl-C6H3 1 v-x F1, 4, 6, 7 =H; R3=H,; R2=H, CH3O; R5=CH3 R8,9=CH2CH2Cl HCl salt, 1 x R1, 4, 6, 7 = H; R3-Cl R2=H; R5=CH3 R8,9=CH2CH2Cl HCl salt, 1 y R1, 4, 6, 7 = H; R3=H; R2=Cl; R5=H R8,9=CH2CH2Cl HCl salt; 1 z R1, 2, 4, 5,6, 7, 8 = H; R3=Cl; R9=CH2-3-Py, 2 a-b R1, 2, 3, 4, 5, 6, 7, 8 = H; R9=quinolin-4-yl, di-N-oxide, 2c R1, 2, 3, 4, 6, 7, 8 =H; R5-CH3; R9=quinolin-4-yl, di-N-oxide 2, 4-di-Cl-C6-H3, 2, 4-di-Br-C6H3, 1 e-h R1, 2, 3, 4, 5, 6, 7, 8 = H; R9=4-Cl-C6H4, 2, 4-di-Cl-C6H3, in each case in the form of the N-oxide and the HCl salt, 1 i R1, 2, 3, 4, 5, 6, 7, 8 = H; R9=4-Br-C6H4, HBr salt, 1 j-k R1, 2, 3, 4, 6, 8 = H; R5=CH3; R7=H, CH3; R9=C6H5 1 m R1, 3, 4, 6, 7, 8 = H; R2, 5=CH3; R9=C6H5, 1 n R1=O-CH3; R2, 3, 4, 6, 7, 8 = H; R5=CH3; R9=C6H5 HCl salt, 1 o-q R1, 3, 4, 5, 6, 7, 8 = H; R2=CH3; R9=4-NO2-C6H4; Hcl salt, N-oxide 1 r-s R1, 2, 4, 5, 6, 7, 8 = H; R3=Cl; R9=4-NO2-C6H4; 4-Cl-C6H4 1 t-u R1, 2, 3, 4, 6, 7, 8 = H; R5=Cl; R9=4-Cl-C6H4; 2, 4-di-Cl-C6H4 1 v-x R1, 4, 6, 7 = H; R3=H,; R2=H CH3O; R5=CH3 R8,9=CH2CH2Cl HCl salt, 1 x R 1, 4, 6, 7=H; R3=Cl R2=H; R5=CH3 R8,9=CH2CH2Cl HCl salt, 1 y R 1, 4, 6, 7=H; R3=H, R2=Cl; R5=H R8,9=CH2CH2Cl HCl salt, 1 z R1, 2, 3, 4, 5, 6, 7, 8=H; R3=Cl; R9=CH2-3-Py, 2 a-b R1, 2, 3, 4, 5, 6, 7, 8=H; R9=quinoline-4-yl, di-N-oxide, 2 c R1, 2, 3, 4, 6, 7, 8=H; R5=CH3, R9=quinoline-4-yl, di-N-oxide, 2 d-o R1, 2, 3, 4, 5, 6=H; R9=C6H5, C6H5 N-oxide, 4-Cl-C6H4, 4-Cl-C6H4-N-oxide, 4-Br-C6H4, 4-Br-C6H4 N-oxide, 2, 4-Cl-C6H3, 2, 4-Cl-C6H3, N-oxide, 2-4-Br-C6H3, 2, 4-Br-C6H3, N-oxide, 4-(CH3)2N-C6H4, 4-(CH3)2N-C6H4 N-oxide, 2 p-q R1 3, 6=H; R5=CH3, R9=C6H5; R2=OCH3, R4=OCH3. 2 r-s R1 3, 6=H; R5=CH3, R9=C6H5; R2=OCH2CH3; R4=OCH2CH3; 2 t-v R1, 2, 3, 4, 6=H; R5=Cl; R9=C6H5, 4-Cl-C6H4, 2, 4-Cl-C6H3, 2 w R1, 2, 4, 5, 6=H; R3=Cl; R9=C6H5, 2 x R1, 2, 3, 4, 6=H; R5=CH3; R9=C6H5, 2 y R1, 2, 3, 4=H; R5,6=CH3; R9=C6H5, 2 z R2, 3, 4, 6=H; R1,5=CH3; R9=C6H5, 3 a R1, 3, 4, 6=H; R2, 5=CH3; R9=C6H5, 3 b R1, 2, 3, 6=H; R4, 5=CH3; R9=C6H5, 3 c R2, 4, 6=H; R1, 3, 5=CH3; R9=C6H5, 3 d R1, 3, 6=H; R2, 4, 5=CH3; R9=C6H5,