Verfahren zur Herstellung von in 2-Stellung substituierten Benzoxazinonen

摘要

The invention comprises compounds of the formula wherein R2, R3, R4 and R5 are hydrogen, halogen, alkyl, aryl, alkoxy, aroxy, acyloxy, alkylmercapto, arylmercapto, cyano, cyanato, isocyanato, alkylamino, acylamino, sulphamino, sulphonic, sulphonic ester or amide, carboxy, carbalkoxy, carbanoxy, carbamino, aldehyde, acyl benzoxazinonyl or nitro, or wherein any two adjacent radicals are members of an aliphatic or aromatic ring system which may contain further hetero atoms, or the radical of the formula and Y is -OR6, or S-R8, where R6 is an aromatic radical, R7 a hydrogen atom, a hydroxyl, aliphatic, aromatic radical, a heterocyclic radical or NR9R10; R8, R9 and R10 ar hydrogen, or an aliphatic, aromatic or heterocyclic radical or R7 and R8 or R9 and R10 may together with the nitrogen form a heterocyclic ring which may contain further hetero atoms. The compounds are prepared by reacting a cyanic acid ester of the formula wherein R1 is an aliphatic, aromatic or heterocyclic radical, with a compound of the formula HY which has a reactive hydrogen atom, or salts of such a compound, at - 50 DEG -180 DEG C. in a solvent. In this process intermediates of the formula may be isolated in the form of their salts with hydrochloric, sulphuric or acetic acids. The intermediates are converted to benzoxazinones by heating in a high-boiling solvent in the presence of an alkali hydroxide, -carbonate, -alcoholate or triethylamine. Many examples are given. The compounds show herbicidal fungicidal and insecticidal properties, and may be used in photographic emulsions.ALSO:Herbicidal properties against mustard in cereal-cultures and fungicidal properties are shown by solutions of compounds of the formula wherein R2, R3, R4 and R5 are hydrogen, halogen, alkyl, aryl, alkoxy, aroxy, acyloxy, alkylmercapto, arylmercapto, cyano, cyanato, isocyanato, alkylamino, acylamino, sulphamino, sulphonic, sulphonic ester or amide, carboxy, carbalkoxy, carbaroxy, carbamino, aldehydro, acyl benzoxazinonyl or nitro, or two adjacent Rs form a ring, Y is -OR6 -N or S-R8, where R6 is an aromatic radical, R7 is hydrogen, hydroxy, or amine or hydrocarbon or heterocyclic radical, R8 is hydrogen, hydrocarbon or heterocyclic radical or R7 and R8 together with the nitrogen may form a ring.