Patent GB-769181-A (GB)
Title: Process for the production of new acylated cyclic hydrazides and fungicidal compositions containing them
IPC: C07D237/16
Filed: 1955-05-24
Abstract: The invention comprises derivatives of dicarboxylic acid hydrazides of the general formula <FORM:0769181/IV(b)/1> wherein R represents a vicinal divalent hydrocarbon radical and R1 represents hydrogen or a monovalent hydrocarbon radical, the whole molecule containing at most one aromatic nucleus.  Such compounds are obtained by reacting one mol. of trichloromethane sulphenyl chloride (perchloro-methyl mercaptan) with one mol. of a dicarboxylic acid hydrazide of the general formula <FORM:0769181/IV(b)/2> either as its alkali metal salt or in the presence of an acid binding agent.  R can, for example, represent the ethylene, ethenylene, cyclohexenylene or o-phenylene radical and R1 can represent hydrogen or the methyl, ethyl, isopropyl, cyclohexyl, phenyl or benzyl radical.  In examples: (1) N-phenyl succinic acid hydrazide dissolved in caustic soda lye is reacted with perchloromethyl mercaptan to give N-phenyltrichloromethane sulphenyl succinic acid hydrazide.  The N-ethyl derivative and (2) N-methyl-trichloromethane sulphenyl phthalic acid hydrazide are prepared in a similar manner.ALSO:Fungicidal derivatives of dicarboxylic acid hydrazides of the general formula: <FORM:0769181/I/1> wherein R represents a vicinal divalent hydrocarbon radical and R1 represents hydrogen or a monovalent hydrocarbon radical, the whole molecule containing at most one aromatic nucleus (see Group IV(b)) are used dispersed in water or air, in dusting powders or dissolved in organic solvents, to treat seeds, bulbs and tubers.  In an example a dusting powder comprises 2 to 15 parts of N-phenyl trichloromethane sulphenyl succinic acid hydrazide and 98-95 parts of talc.  Kaolin, bole, bentonite, chalk or limestone may be used instead of talc.ALSO:Products having fungicidal activity comprise derivatives of dicarboxylic acid hydrazides of the general formula <FORM:0769181/VI/1> where R represents a vicinal divalent hydrocarbon radical (e.g. an ethylene, ethenylene, cyclohexenylene or o-phenylene radical and R1 represents hydrogen or a monovalent hydrocarbon radical (e.g. a methyl, ethyl, isopropyl, cyclohexyl, phenyl or benzyl radical), the whole molecule containing at most one aromatic nucleus.  The compounds may be employed in compositions containing also insecticidal, acaricidal or other fungicidal substances, and suitable carriers are talc, kaolin, bole, bentonite, chalk or ground limestone.  Wetting and dispersing agents may be added.  The active ingredients can also be employed in solution in chlorinated hydrocarbons, petroleum fractions or acetone or as an aerosol distributed as smoke or steam.  Examples describe compositions of (3) active ingredient, such as N-phenyl trichloromethane sulphenyl succinic acid hydrazide and talc, to which adhesive may be added; (4) N-ethyl trichloromethane sulphenyl phthalic acid hydrazide, kaolin or chalk, and wetting and dispersing agents such as sulphite waste liquor and ethylene oxide condensation products of alkyl phenols being concentrate suitable for mixing with water; (5) trichloromethane sulphenyl maleic acid hydrazide, xylene and ethylene oxide condensation products of alkylphenols being an emulsion concentrate.  The preparation of the hydrazides is described (see Group IV(b)).