PROCESS FOR THE PREPARATION OF 4,5-BIS-TRIFLUOROMETHYL-IMINO-DERIVATIVES OF SULPHUR-FREE HETEROCYCLIC FIVE-MEMBERED RINGS WITH TWO RING HETERO ATOMS

摘要

1421691 4,5-Bis-trifluoromethylimino-imidazole derivatives BAYER AG 30 April 1974 18881/74 Addition to 1355548 Heading C2C Novel 4,5-bis-trifluoromethylimino derivatives of imidazole of the general formula in which: when X is oxygen and R 1 is phenyl, R 2 may be ethyl, n-propyl, i-propyl, n-butyl, ibutyl, t-butyl, prop- 1-enyl, cyclohexyl, methoxyethyl, nitrilo-n-pentyl or phenylethyl; when X is oxygen and R 1 is methyl, R 2 may be a phenyl group having 2-chloro-, 3-chloro-, 3,5-dichloro- 2-methyl-, 3-methyl-, 4-methyl-, 4-ethyl-, 3- ethoxy-, 4-ethoxy-, 3,4-dimethyl-, 2,4-dichloro-, 2,6-dimethyl-, 2,6-diethyl-, 2-methoxy-, 2,3-dimethyl-, 2-i-propyl-, 2,4,5-trimethyl-, 3- methoxy-, or 2-methyl-4-chlorosubstituents or may be a phenyl-ethyl group; when X is oxygen and R 1 is 3,4-dichlorophenyl, R 2 may be ethyl, n-propyl, i-propyl, n-butyl, cyclohexyl, benzyl or methoxyethyl; when X is oxygen and R1 is methoxyethyl, R 2 may be a phenyl group having 2,4-dichloro-, 2-methyl-, 4-ethoxy-, 4- methyl-, 3-methyl-, 4-chloro-, penta-chloro-, 2-i-propyl-, 2,4-dimethyl-, 2,3-dimethyl-, 2- ethyl-, 3-chloro-4-methyl-, 2,6-diethyl-3,4,5- trichloro-, 2-methoxy-4-chloro-5-methyl-, 2- methoxy-, 3-methoxy-, 3-methoxy-4-methyl-, 3-cyano-, or 3-nitro substituents; when X is N-CO-OCH 3 and R 1 is methoxycarbonyl, R 2 may be phenyl, benzyl, 4-methoxyphenyl, or 3,4-dichlorophenyl; and when X is N-phenyl, R 1 is methyl and R 2 is phenyl, are prepared by reacting a compound of general formula with perfluoro-2,5-diazahexa-2,4-diene, (CF 3 N = CF-)- 2 , in the presence of a HF acceptor at -50‹ to + 120‹ C. Amongst numerous examples the compounds 1-phenyl-3-ethyl-4,5-bistrifluoromethylimino-imidazole-2-one and 1- phenyl - 2 - phenylimino - 3 - methyl - 4,5 - bistrifluoromethylimino-imidazole are prepared. Fungicidal, insecticidal or acaricidal compositions contain a compound of Formula I as active ingredient in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.