Patent GB-955492-A (GB)
Title: ª-thiocarbamoyl-benzaldoximes, their salts and esters and compositions containing them
Inventor: YATES JOHN
IPC: C07C333/02
Filed: 1961-11-27
Abstract: The invention comprises a -thiocarbamoyl benzaldoximes and their salts and esters, the benzene nucleus thereof being substituted by a chlorine atom in the para position or in each ortho-position. The compounds may be syn-or anti-isomers or mixtures thereof.  The salts may be alkali metal, alkaline earth metal, ammonium or substituted ammonium.  The esters may be of carboxylic acids, e.g. aliphatic or chlorinated aliphatic carboxylic acids of 1 to 4 carbon atoms, or of sulphonic, phosphoric or phosphonic acids.  The novel compounds may be made by reaction of hydrogen sulphide with the corresponding a -cyanobenzaldoxime, or its salt or ester. The hydrogen sulphide may be used as such or may be formed in situ from a suitable compound, for example, thionacetamide The reaction may be effected by heating the reactants together in a solvent, such as dimethyl formamide, aliphatic ketones or aromatic hydro-carbons. Temperatures of 90 to 100 DEG C. are suitable with dimethyl formamide. As a source of hydrogen sulphide, there may be used a thionothiolo-phosphonic, phosphonic or phosphinic acid of formula R1R2PS.SH wherein R1 and R2 each represent an alkyl, aryl or an alkyl linked directly or through oxygen to the phosphorus atom, in the presence of a hydrogen halide, e.g. hydrogen chloride, and in the presence or absence of a solvent in the temperature range of 30 to 60 DEG C.  Detailed examples of the preparation of a -thiocarbamoyl-2, 6-dichlorobenzaldoxime and a -thiocarbamoyl-4-chlorobenzaldoxime are given.  According to the Provisional Specification, the benzene nucleus of the benzaldoxime may contain one to five halogen substituents, which are preferably chlorine or bromine, but fluorine or iodine are also possible.  No further examples are given.ALSO:A pesticidal composition comprises an a -thiocarbamoyl benzaldoximes or salt or ester thereof, a number of salts and esters are specified, the benzene nucleus being substituted by a chlorine atom in the para-position or in each ortho-position, and a surface-active agent, or a carrier, or a surface-active agent and a carrier.  The composition may be a dust, a wettable powder, a solution in an organic solvent, an emulsifiable concentrate, granules or pellets, or an aqueous emulsion or dispersion.  Solid carriers include clays, synthetic hydrated silicon oxides and calcium silicates, sulphur or carbon, natural or synthetic resins, bitumen, asphalt or waxes.  Liquid carriers include water, petroleum fractions, ketones, hydrocarbons and chlorinated hydrocarbons. Alcohols, ketones and polyalkylene glycol polyethers are suitable auxiliary solvents.  The carrier may be a simple or compound fertilizer.  Suitable wetting, dispersing and emulsifying agents are specified.  Water conditioning agents are specified and other herbicides or pesticides may be present.  Pharmaceutical compositions for use as general metabolic depressants comprise an a -thiocarbamoyl benzaldoxime, salt or ester as specified above, and a pharmaceutical solid or liquid carrier.  Preparations for oral ingestion may be syrups, elixirs, powders, tablets or capsules.  For parenteral administration, sterile solutions or suspensions in water, physiological saline, p  benzyl alcohol or ethyl oleate may be used, with suitable diluents and/or excipients if desired.  According to the Provisional Specification, the benzaldoxime may contain one to five halogen atoms, preferably chlorine or bromine, but possibly fluorine or iodine.  No further examples are given.