Patent GB-950348-A (GB)
Title: Plant growth regulants
IPC: C07D493/08
Filed: 1961-11-30
Abstract: A plant growth regulant composition comprises as active ingredient a compound selected from the group consisting of N-disubstituted-amino amic acids in which the disubstituted amino radical is any of dialkylamino radicals having 1 to 12 carbon atoms in each alkyl group, 1 - pyrrolidyl, 1 - piperidyl, or 4 - morpholinyl radicals, and the amic acid is any of hexahydrophthalamic acid, 1,2,3,6-tetrahydrophthalamic acid, 3,6 - endoxy - D 4 - tetrahydrophthalamic acid, and 3,6 - endomethylene - D 4 - tetrahydrophthalamic acid, and the salts and imids of the N-disubstitutedamino amic acids.  Specified active ingredients are N-dimethylaminohexahydrophthalamic acid, N - dimethyl-amino - 1,2,3,6 - tetrahydrophthalamic acid, N - dimethylamino - 3,6 - endoxy - D 4 -tetrahydrophthalamic acid, N - dimethylamino3,6 - endomethylene - D 4 - tetrahydrophthalamic acid, N - dimethylamino - 3,6 - endomethylene - D 4 - tetrahydrophthalimide.  The composition may be in the form of dusts with powdered solid carriers such as mica, talc, pyrophillite and clays or an aqueous solution or as solutions in organic solvents e.g. acetone, benzene or kerosene.  Surface-active agents may be added to each of these forms of the composition. The invention comprises methods of regulating plant growth by applying the compounds to plants i.e. seeds, flowers, fruits, vegetables, roots and foliage or to soil in which seeds are planted.  Examples given show the dwarfing effect on plants of the compounds. U.S.A. Specification 2,547,724 is referred to.ALSO:The invention comprises an N-disubstituted aminoamic acid in which the disubstituted amino radical is any of dialkylamino radicals having 1 to 12 carbon atoms in each alkyl group, 1-pyrrolidyl, 1-piperidyl, or 4-morpholinyl radicals, and the amic acid is any of hexahydrophthalamic acid, 1, 2, 3, 6-tetrahydrophthalamic acid, 3, 6-endoxy-D 4 -tetra-hydrophthalamic acid, and 3, 6-endomethylene-D 4 -tetrahydrophthalamic acid, and the salts and imides of the N-disubstituted amino amic acids.  Per se compounds claimed are N-dimethylaminohexahydrophthalamic acid, N-dimethylamino-1, 2, 3, 6-tetrahydrophthalamic acid, N-dimethylamino-3, 6-endoxy-D 4 -tetrahydrophthalamic acid, N-dimethylamino-3, 6-endomethylene-D 4 -tetrahydrophthalamic acid, N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalimide. The N-disubstituted amino amic acids are prepared by reacting the selected 1, 1-disubstituted hydrazine with the anhydride of the selected dicarboxylic acid.  The imides of these acids are prepared by removing water from the acid by means of acetic anhydride.  The salts may readily be formed directly from the acid and a selected base such as an alkali-metal hydroxide or carbonate, or ammonia, or an amine.  In an example N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalamic acid is prepared by reacting 1, 1-dimethylhydrazine with 3, 6-endomethylene-D 4-tetrahydrophthalamic anhydride.  The N-dioctylamino, N-didodecylamino, N-(4-morpholinyl), N-(1-pyrrolidyl) and N-(1-piperidyl)-3, 6- endomethylene-D 4-tetrahydrophthalamic acids may similarly be prepared from 1, 1-dioctyl hydrazine, 1, 1-didodecyl-hydrazine, N-aminomorpholine, N-aminopyrrolidine, and N-aminopiperidine, respectively and 3, 6-endomethylene-D 4-tetrahydrophthalic anhydride.  The other N-disubstituted amino amic acids may similarly be prepared from the anhydride of the selected hydrophthalic acid.  In another example N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalimide is prepared by reacting N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalamic acid with acetic anhydride. Other examples show the production of N-dimethylaminohexahydrophthalamic acid, -1, 2, 3, 6-tetrahydrophthalamic acid, -3, 6, endoxy-D 4,tetrahydrophthalamic acid.  U.S.A. Specification 2,547,724 is referred to.