PROCESS FOR PREPARING PYRIDINIUM-ALKANOYL-QUINOLINE DERIVATIVES

摘要

1505427 Quinoline derivatives CHINOIN GYOGYSZER ES VEGYASZETI TERMEKEK GYARA RT 4 June 1976 [6 June 1975] 23286/76 Heading C2C Novel quinoline derivatives having the general formula wherein n is 0 or 1; R is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted aralkyl; R1 is hydrogen, halogen, optionally substituted alkyl optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl of cycloalkylalkyl, optionally substituted amino, hydroxy, optionally substituted alkoxy, optionally substituted aralkoxy, optionally substituted acyl, nitro, carboxylic acid, carboxylic acid derivative, or an optionally substituted five-, six- or seven-membered heterocyclic ring containing one, two or three nitrogen heteroatoms and being attached to the quinoline ring through one of the nitrogen atoms; R2 is hydrogen, halogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted amino, nitro, hydroxy, optionally substituted alkoxy, optionally substituted aralkoxy or optionally substituted aryloxy; R3 is hydrogen, halogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted amino, hydroxyl, optionally substituted alkoxy, or optionally substituted aryloxy; or R2 and R3 may form together with the 5,6-, 6,7- or 7,8-side of the quinoline ring an optionally substituted five-, six- or seven-membered ring optionally containing one or two heteroatoms selected from oxygen, sulphur and nitrogen; and when n = 0, and R3 is attached to 3-position of the quinoline ring, R3 and R may form together an optionally substituted -(CH 2 ) m -chain, wherein: m is 2, 3 or 4; R4 is hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl or optionally substituted cycloalkyl or cycloalkylalkyl; R5 is hydrogen, optionaly substituted alkyl, optionally substituted aryl or optionally substituted aralkyl; Y is an aromatic heterocyclic ring, containing a tertiary nitrogen atom, and being attached through the nitrogen, or Y is a trialkylamino group; Z is an anion; X is oxygen or sulphur, and salts thereof where such can exist, are prepared by either (a) reacting a compound of the formula with an aromatic tertiary base or trialkylamine YH in the presence of a halogen, or (b) reacting a compound of the formula with an aromatic tertiary base or trialkylamine YH, and optionally replacing the halide ion Z- with another anion. The above processes are preferably carried out at a temperature of from 50‹ to 150‹ C. The novel compounds possess fungicidal, insecticidal and herbicidal properties.