Patent GB-840121-A (GB)
Title: New organic ú•ú¾ú´thiocyanates
Inventor: STEVENSON HERBERT AUBREY
IPC: C07C331/28
Filed: 1956-02-03
Abstract: The invention comprises compounds of the general formula <FORM:0840121/IV(b)/1> in which the phenyl radical X is substituted by an iso-thiocyanato radical and may be additionally substituted by one or more halogen atoms or alkyl radicals and R represents an alkyl radical (excepting ethyl), an alkenyl radical, a halogenated alkenyl radical, an alkyl radical substituted by one or more halogen atoms, an acyl radical, a phenyl radical or a halogenated phenyl radical. They may be prepared by the action of thiophosgene on a compound of the formula <FORM:0840121/IV(b)/2> where the phenyl radical Y contains an amino group and R is as previously defined.  The thiophosgene may be prepared in situ by reducing trichloromethane sulphenyl chloride with stannous chloride.  The amino sulphone may be prepared by reacting a thiol <FORM:0840121/IV(b)/3> with a halogen compound R-hal to form a sulphide, oxidizing this sulphide with hydrogen peroxide to the corresponding sulphone, nitrating in the ring with a nitrating mixture and then reducing this nitro compound to the corresponding amine.  These iso-thiocyanates may be used as dusts, dispersions, emulsions, smokes and aerosols to retard the development of fungi.  The following compounds are described in examples and melting points and analysis figures are given: the iso-thiocyanate group in the para position to the sulphonyl group; R is methyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, amyl, 1-methylbutyl, 3-methylbutyl, hexyl, heptyl, octyl, cetyl, allyl, 3-chloroallyl, acetonyl, benzyl, phenacyl, 2-phenylethyl, p-chlorobenzyl, chloromethyl, 1 : 1 - dimethyl - 3 - oxobutyl, bromomethyl, 2-chloro-ethyl and dichloromethyl; the iso-thiocyanate group meta and a methyl group para to the sulphonyl group; R is methyl, propyl and butyl; the iso-thiocyanate group meta and a chlorine group para to the sulphonyl group; R is methyl, propyl, isopropyl, butyl, iso-butyl, amyl and 3-methylbutyl. Meta-methyl-sulphonylphenyl iso-thiocyanate is also described.  The preparation, melting point and analysis figures are given for the corresponding sulphides, sulphones, nitrosulphones and amino-sulphones (compound II) of a large number of the iso-thiocyanates. Specification 796,754 is referred to.ALSO:A fungicidal composition comprises an inert diluent and as active compound a compound of the general formula <FORM:0840121/VI/1> where the phenyl nucleus X is substituted by an iso-thiocyanato radical and may additionally be substituted by one or more halogen atoms or alkyl radicals, and R represents a methyl radical, an alkenyl radical, a haloalkenyl radical, an alkyl radical containing at least three carbon atoms or an alkyl radical substituted by one or more halogen atoms, an acyl radical, a phenyl radical or a halogenated phenyl radical.  The composition may be any of the usual solid or liquid forms and the usual diluents including wetting agents, dispersants and emulsifiers, other insecticides and fungicides such as D.D.T., sulphur and benzene hexachloride.  There may also be included an ignitable slow burning composition.  Many active compounds and diluents are mentioned and the examples describe the preparation of a dust, dispersable powders and aerosols.  Specification 796,754 is referred to.