Patent GB-840122-A (GB)
Title: New organic sulphonamido úú¾ú´thiocyanates
Inventor: STEVENSON HERBERT AUBREY
Filed: 1956-02-03
Abstract: The invention comprises compounds of the general formula <FORM:0840122/IV(b)/1> in which the phenyl radical X is substituted by an iso-thiocyanato radical, R1 is hydrogen or an alkyl radical and R2 is an alkyl radical, an alkyl radical containing a phenyl substituent, a cycloalkyl radical, an alkenyl radical, a phenyl radical or a phenyl radical containing one or more halogen, alkyl, alkoxy or nitro substituents or R1 and R2 together with the nitrogen atom form a heterocyclic residue derived from a heterocyclic compound containing a secondary nitrogen atom such as piperazine, morpholine or partially or completely reduced pyridine and pyrrole compounds. They may be prepared by the action of thiophosgene on a compound of formula <FORM:0840122/IV(b)/2> where the phenyl radical Y contains an amino group and R1 and R2 are as defined above.  The thiophosgene may be prepared in situ by reducing trichloromethane sulphenyl chloride with stannous chloride.  The amino compound may be prepared by reacting a compound R1R2NH with a compound <FORM:0840122/IV(b)/3> where R1 and R2 are as defined above and the amino substituent on Y is protected by acylation.  The acylamino sulphonamide thus obtained is then hydrolysed to obtain the amino sulphonamide.  The compounds may be used as dusts, dispersions, emulsions, smokes and aerosols to retard the development of fungi. The preparation of the following compounds is described in examples: the isothiocyanato radical para to the sulphonamide group; R1 is hydrogen; R2 is methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl, pentyl, 3-methylbutyl, heptyl, 4-methylpentyl, octyl, dodecyl, allyl, cyclo-hexyl, phenyl, benzyl, p-chlorophenyl, o-chlorophenyl, m-chlorophenyl, p-methoxyphenyl, o-methoxyphenyl, p-ethoxyphenyl, m-nitrophenyl, p-tolyl, o-tolyl; R1 and R2 both methyl, ethyl, n-propyl, nbutyl, iso-butyl, pentyl; R2 phenyl and R1 methyl, ethyl, n-propyl, n-butyl; R2 benzyl and R1 methyl; R1 and R2 together with the nitrogen atom forming derivatives of the following heterocyclic compounds; piperidine, morpholine, pyrrolidine, 2-methylpiperidine, 3-methylpiperidine, 4-methylpiperidine and D 3-tetrahydro - pyridine, N - ethyl - m - iso - thiocyanato benzenesulphonamide is also described.  Melting points and analysis figures are given for all the above compounds.  The preparation, melting point and analysis figures are also given for the corresponding amino compounds for most of the iso-thiocyanates mentioned.ALSO:A fungicidal composition comprises an inert diluent and as active compound a compound of the formula <FORM:0840122/VI/1> in which the phenyl nucleus X is substituted by an iso-thiocyanate radical, R1 is hydrogen or an alkyl radical, R2 is an alkyl radical, an alkyl radical containing a phenyl substituent, a cycloalkyl radical, an alkenyl radical, a phenyl radical or a phenyl radical containing one or more halogen atoms or alkyl, alkoxy or nitro groups as substituents or R1 and R2 together with the nitrogen atom represent a heterocyclic radical derived from a heterocyclic compound containing a secondary nitrogen atom.  The composition may be any of the usual solid or liquid forms and the usual diluents including wetting agents, emulsifiers and dispersants may be added. Many active compounds and diluents are mentioned and the examples describe the preparation of a dust, dispersable powders and aerosols.