GB555795A - Manufacture of new organic sulphur-containing compounds - Google Patents

Abstract

555,795. Pesticidal compounds. GUDGEON, H., HARLAND, J. C., SEXTON, W. A., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Jan. 14, 1942, No. 550. [Class 2 (iii)] [Also in Group VI] Compounds which are useful for pesticidal purposes and are ring compounds containing one sulphur, two nitrogen and three carbon atoms in a symmetrical ring in which the carbon atoms are meta to one another are prepared by interaction of an aryldithiocarbamic acid or a salt thereof with one chemically equivalent proportion of a primary aliphatic (including cycloaliphatic) monoamine and two chemically equivalent proportions of formaldehyde. Attached to one nitrogen atom of the ring is an aryl radical which may contain as substituents alkyl, halogeno, alkoxy, hydroxy, amino, substituted amino or carboxy groups, and to the other an alkyl or cycloalkyl radical which .may contain a hydroxyl group. Amines include methyl-, ethyl-, isopropyl-, and isobutylamine, and their higher homologues, hydroxyamines such as #-ethanolamine, and cycloaliphatic amines such as cyclohexylamine, and they may be used as their neutral or acid salts with mineral acids or as alkylammonium aryldithiocarbamates. Examples are given of products obtained from methylammonium phenyldithiocarbamate, methylammonium α- naphthyldithiocarbamate, methylammonium ptolyldithiocarbamate, methylammonium phydroxyphenyldithiocarbamate, and methylammonium p-carboxyphenyldithiocarbamate. Other amines which may be used to produce the aryldithiocarbamate are p-chloroaniline, p-anisidine, p-aminodimethylaniline, p- and m-aminoacetanilide, and p- and m-phenylenediamine. Specification 368,509 is referred to.