Patent GB-782978-A (GB)
Title: Fungicides
Filed: 1954-02-23
Abstract: Quinone-oxime-acylhydrazones having the formula: [HO-N = R = H-NH-X-]nR1 in which R is a mono- or multi-nuclear quinoidal aromatic radical, R1 is hydrogen or an amine or organic radical, X is <FORM:0782978/IV (a)/1> and n is an integer not higher than 2. and in which R may be <FORM:0782978/IV (a)/2> where Y is halogen preferably chlorine and m is 0, 1 or 2, R1 a hydrogen or an alkyl, aralkyl, aryl or amino radical and n is 1, or Y is a C1 to C4 alkyl radical, or when m is 0, R1 is OR4, R4 being a C1 to C4 alkyl radical, or NR5R6,R5 and R6 being hydrogen, C1 to C4 alkyl, aralkyl or phenyl, are prepared by condensation of quinone monoximes or nitrosophenols with carboxylic acid hydrazides, thiocarboxylic acid hydrazides, sulphonic acid hydrazides, semicarbazides, thiosemicarbazides, or aminoguanidines.  Examples of hydrazides are hydrazides of the following acids: a benzoic, alkylbenzoic, halogenobenzoic, nitrobenzoic, aminobenzoic, dimethylaminobenzoic, hydroxybenzoic, alkoxybenzoic, phenoxybenzoic, formic, acetic, cyanoacetic, propionic, valeric, lauric, crotonic, cinnamic, hydroxybutyric, hydroxyisovaleric, hydroxyacetic, alkoxyacetic, phenoxyacetic, thioacetic, methylthioacetic, alkylcarbonic, phenylcarbonic, phenylacetic, aminoacetic, naphthoic, naphthylacetic, pyromucic, thiocarbonic and succinic acid, the dihydrazides of malonic and oxalic acids, and carbohydrazide.  Methyl- and dimethylaminoacetic acid hydrazide, trimethyl ammonium chloride acetic acid hydrazide or pyridinium chloride acetic acid hydrazide may be employed in the form of their salts, e.g. chloride, nitrate, phosphate, dithiocarbonate, thiocyanate, dinitrophenolates, pentachlorophenolates.  The products obtainable from nitrosophenols, semicarbazide, phenylsemicarbazide, thiosemicarbazide, phenylthiosemicarbazide, dithiocarbazinic acid esters, aminoguanidine and benzene sulphonic acid hydrazide are also suitable.  Suitable quinone components are quinone monoxime, nitrosophenol, alkylnitrosophenols, halogenonitrosophenols, nitrosonaphthols and other quinone compounds capable of reacting with the above hydrazides.  A large number of hydrazones including quinone - oxime - benzoyl - hydrazone, are specified in the examples. Specification 726,684 is referred to.ALSO:A fungicidal composition contains as an active fungicidal substance a quinone-oxime-acylhydrazone having the formula [HO-N=R=N-NH-X-]nR1 in which R is a mono- or multi-nuclear quinoidal aromatic radical, R1 is hydrogen or an amino or radical, X is <FORM:0782978/VI/1> or and n is an integer not higher than 2, or a salt thereof, and a carrier.  R may be <FORM:0782978/VI/2> where Y is halogen, preferably chlorine, and m is 0, 1 or 2, R1 an hydrogen or an alkyl, aralkyl, aryl or amino radical and n is 1.  Alternatively, Y is a C1 to C4 alkyl radical.  Preferably when m is 0, R1 is OR4, R4 being a C1 to C4 alkyl radical, or NR5R6, R5 and R6 being hydrogen, C1 to C4 alkyl, aralkyl or phenyl.  The compounds are prepared by condensation of quinone monoximes or nitrosophenols with carboxylic acid hydrazides, thiocarboxylic acid hydrazides, sulphonic acid hydrazides, semicarbazides, thiosemicarbazides, or aminoguanidines.  Examples of hydrazides are hydrazides of the following acids: benzoic, alkylbenzoic, halogenobenzoic, nitrobenzoic, aminobenzoic, dimethylaminobenzoic, hydroxybenzoic, alkoxybenzoic, phenoxybenzoic, formic, acetic, cyanoacetic, propionic, valeric, lauric, crotonic, cinnamic, hydroxybutyric, hydroxyisovaleric, hydroxyacetic, alkoxyacetic, phenoxyacetic, thioacetic, methylthioacetic, alkylcarbonic, phenylcarbonic, phenylacetic, aminoacetic, naphthoic, naphthylacetic, pyromucic, thiocarbonic and succinic acid, the dihydrazides of malonic and oxalic acids, and carbohydrazide. Methyl-, and dimethylaminoacetic acid hydrazide, trimethyl ammonium chloride acetic acid hydrazide or pyridinium chloride acetic acid hydrazide may be employed in the form of their salts, e.g. chloride, nitrate, phosphate, dithiocarbonate, thiocyanate, dinitrophenolates, pentachlorophenolates.  The products obtainable from nitrosophenols, semicarbazide, phenylsemicarbazide, thiosemicarbazide, phenylthiosemicarbazide, dithiocarbazinic acid esters, aminoguanidine and benzene sulphonic acid hydrazide are also suitable.  Suitable quinone components are quinone monoxime, nitrosophenol, alkylnitrosophenols, halogenonitrosophenols, nitrosonaphthols and other quinone compounds capable of reacting with the above hydrazides.  A large number of hydrazones including quinone-oxime-benzoylhydrazone, are specified in the examples. Specification 726,684 is referred to.