Abstract:
Certain novel 4-amino-1,2,4-triazine-5-one compounds of the formula:
in which R1 and R4 are hydrogen, alkyl, cycloalkyl, substituted phenyl or phenyl; R2 is hydrogen or alkyl; R3 is hydrogen, alkyl, phenyl, haloalkyl, phenylalkyl, or alkylphenyl, alkoxyphenyl or alkylmercaptophenyl; ARE PREPARED BY A NOVEL PROCESS COMPRISING REACTING A GLYOXYLIC ACID ESTER 2-ACYLHYDRAZONE OF THE FORMULA in which R1 and R4 are defined as above, and R is alkyl of from 1 to 4 carbon atoms, IS REACTED WITH A HYDRAZINE DERIVATIVE OF THE FORMULA
in which R2 and R3 are defined as above, IN THE PRESENCE OF AN ORGANIC SOLVENT. The novel compounds are outstandingly active as herbicides and are particularly useful as selective herbicides.
R, R1 AND R2 ARE EACH HYDROGEN, STRAIGHT OR BRANCHED CHAIN LOWER ALKYL OR STRAIGHT OR BRANCHED CHAIN LOWER ALKENYL. X IS STRAIGHT OR BRANCHED CHAIN ALKYL OF 1 TO 12 CARBON ATOMS, STRAIGHT OR BRANCHED CHAIN ALKENYL OF 1 TO 12 CARBON ATOMS OR AN ELECTRONEGATIVE MOIETY, AND N AND N1 ARE EACH INTEGERS FROM 0 TO 2,
OR PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALTS THEREOF ARE PRODUCED BY REACTING DIARYL-PYRIDYL CARBINOLS OF THE FORMULA:
WHEREIN X, N AND N1 ARE AS ABOVE DEFINED, IN AN INERT ORGANIC SOLVENT WITH A REAGENT SUITABLE FOR CHLORINATION OF TERTIARY ALCOHOLS AND REACTING THE DIARYL-PYRIDYL-METHYL CHLORIDE THUS PRODUCED WITH AN ACID-BINDING AGENT AND IMIDAZOLE OR LOWER ALKYL IMIDAZOLE. THE SALTS ARE OBTAINED BY REACTION OF THE COMPOUNDS WITH THE CORRESPONDING ACID. THESE COMPOUNDS ARE USEFUL AS ANTIMYCOTICS AND SHOULD GENERALLY BE ADMINISTERED IN THE RANGE OF ABOUT 20 TO 100 M./KG.
Abstract:
N-methyl-imidazole derivatives of the formula:
OR A PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALT THEREOF, WHEREIN X is an unsubstituted or substituted 6-membered hetero-aromatic moiety having two nitro heteroatoms, Y is an unsubstituted or substituted aliphatic moiety, an unsubstituted or substituted cycloaliphatic moiety, an unsubstituted or substituted aralkyl moiety or an unsubstituted or substituted aryl moiety, and Z is an unsubstituted or substituted aliphatic moiety, an unsubstituted or substituted cycloaliphatic moiety, an unsubstituted or substituted aralkyl moiety, an unsubstituted or substituted aryl moiety, an unsubstituted or substituted pyridyl moiety or an alkoxycarbonyl moiety, ARE USEFUL AS ANTIMYCOTIC AGENTS.
Abstract:
N-carbonic acid derivatives of 1,2-dicarbonylphenylhydrazones, i.e. N-(alkoxy, phenoxy, alkylmercapto, cyclohexyloxy and dialkylamino- -carbonyl and -thiono)-N-(alkyl- and/or electronegative substituent (e.g. halo, haloalkyl, nitro and/or alkyl sulfonyl)- substituted phenyl)-N''-( Alpha -cyano- Alpha (alkanoyl and carboalkoxy)-carbonyl)-hydrazones, which possess arthropodicidal, especially acaricidal and insecticidal, properties and which may be produced by reacting the corresponding alkali metal salt of a 1,2dicarbonylphenylhydrazone, or such 1,2-dicarbonylphenylhydrazone in the presence of an acid-binding agent, with the corresponding carbonic acid chloride.
Abstract:
N-(1,1,1-trisubstituted)-methylazoles are produced by reacting thionyl-imidazole with a substituted carbinol of the formula:
wherein A is aliphatic, cycloaliphatic, aromatic or heteroaromatic, B is aliphatic, cycloaliphatic, aromatic or a 5or 6-membered heteroaromatic ring having 1 to 3 N-heteroatoms or 1 or 2 N-heteroatoms plus an oxygen or sulphur heteroatom and D is aliphatic, cycloaliphatic, aromatic, alkoxycarbonyl, alkoxycarbonylalkyl, aryloxycarbonyl or a 5- or 6-membered heteroaromatic ring having 1 to 3 N-heteroatoms or 1 or 2 Nheteroatoms plus an oxygen or sulphur heteroatom and related carbinols. The reactants are in 1:1 molar ratio and the reaction is carried out in dry inert solvents at a temperature of -20* C. to +150* C.
Abstract:
CERTAIN IMIDAZOLES AND THEIR SALTS HAVING FUNGISTATIC PROPERTIES ARE PROVIDED WHICH HAVE THE FOLLOWING BASIC STRUCTURE:
IMIDAZOL-1-YL-C(-CH Y-1,2-PHENYLENE)
IN WHICH Y IS -(CH2)N-, -CH=CH-, O OR S; A IS N OR CH; AND N IS 0,1,2. TYPICAL FUNGI ARE TRICHOPYTON SPECIES, MICROSPORON SPECIES, CANDIDA SPECIES AND PENICILLIUM SPECIES. THESE COMPOUNDS ARE ALSO ACTIVE AGANIST PATHOGENIC PROTOZOA, VIRUSES AND BACTERIA.
Abstract:
A-(HALO, CYANO, NITRO AND AZIDO)-A-(ALKANOYL, CARBOALKOXY (I.E. ALKOXY CARBONYL), AMINO AND MONO- AND DIALKYL AMINO)-CARBONYL-(UNSUBSTITUTED AND MONO TO PENTA ALKY AND/OR ELECTROEGATIVE SUBSTITUENT (E.G. HALO, NITRO, CYANO, TRIFFUOROMETHYL, TRIFLUOROMETHYL-, -MERCAPTO, -SULFONYL AND -SULFOXYL, ALKOXY, ALKYL SUFONYL AND/OR DIMETHYLMINO SULFONYL)-SUBSTITUTED) PHENYLHYDRAZONES AND THEIR CORRESPONDING ALKALI METAL, ALKALINE EARTH METAL AND AMINE SALTS, WHICH POSSESS PEDTICIDAL, ESPECIALLY ACARICIDAL AND INSECTICDAL, PROPERTIES AND WHICH MAY BE PRODUCED BY CONVENTIONAL METHODS.
Abstract:
N-ACYL-1,2-DICARBONYL-PHENYL-HYDRAZONES, I.E. (A-CYANOA-ALKANOYL AND CARBOALKOXY)-CARBONYL-N-(ALKANOYL, CHLOROALKANOYL, ALKENOYL AND BENZOYL)-((MONO, AND SAME AND MIXED DI AND TRI, -CHLORO AND -TRIFLUOROMETHYL)-PHENYL)HYDRAZONES, WHICH POSSESS ARTHROPODICIDAL, ESPECIALLY ACARICIDAL AND INSECTICIDAL, PROPERTIES.
Abstract:
Diaryl-pyridyl-imidazolyl methanes of the formula
AND PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALTS THEREOF, WHEREIN R1 and R2 are the same or different alkyl of 1 to 4 carbon atoms, ARE PRODUCED EITHER BY A. REACTING A (DIALKYLPHENYL-PHENYL-PYRIDYL)-METHANOL OF THE FORMULA
WHEREIN R1 and R2 are as above defined, with thionyl-bis-imidazole in the presence of an inert organic diluent at a temperature of from -20* C to about 150* C; or B. REACTING A (DIALKYLPHENYL-PHENYL-PYRIDYL)-METHYL HALIDE OF THE FORMULA
WHEREIN R1 and R2 are as above defined and Hal is chlorine or bromine, WITH IMIDAZOLE IN THE PRESENCE OF AN ACID BINDING AGENT AT A TEMPERATURE OF FROM 20* C to about 180* C. The diaryl-pyridyl-imidazole methanes of the present invention are useful for their antimycotic activity.