IE43946L - Oxadiazinone derivatives - Google Patents

Abstract

1501589 1,2,4-Oxadiazin-5-one derivatives PHILAGRO 8 Sept 1976 [11 Sept 1975] 37226/76 Heading C2C Novel 1,2,4-oxadiazin-5-one derivatives having the general formula wherein R represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms, or a phenyl radical, and Ar represents a phenyl radical substituted by 1, 2 or 3 substituents, which-when two or three substituents are present-may be identical or different, selected from halogen atoms, the hydroxy radical, alkyl radicals containing 1 to.4 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms, alkylthio radicals containing 1 to 4 carbon atoms, alkylsulphinyl radicals containing 1 to 4 carbon atoms, alkylsulphonyl radicals containing 1 to 4 carbon atoms, the trifluoromethyl, trifluoromethoxy, trifluoromethylthio and carboxy radicals, alkoxycarbonyl radicals containing 2 to 5 carbon atoms, the nitro and amino radicals, alkylamino radicals containing 1 to 4 carbon atoms in the alkyl group, dialkylamino radicals containing 1 to 4 carbon atoms in each alkyl group, acylamino radicals containing 1 to 4 carbon atoms in the acyl moiety, alkoxycarbonylamino radicals containing 1 to 4 carbon atoms in the alkoxy group, the azido radical, alkanoyl radicals containing 1 to 4 carbon atoms, the sulphamoyl radical, dialkylsulphamoyl radicals containing 1 to 4 carbon atoms in each alkyl group, or the phenyl radical, or Ar represents a mononuclear aromatic heterocyclic radical with 5 atoms in the ring, the hetero atom being oxygen, sulphur or nitrogen, said heterocyclic radical being unsubstituted or substituted by a halogen atom, an alkyl radical containing 1 to 4 carbon atoms, a phenylalkyl radical containing 1 to 4 carbon atoms in the alkyl moiety, an alkoxy radical containing 1 to 4 carbon atoms or an alkylthio radical containing 1 to 4 carbon atoms, are prepared by either (a) cyclizing an amidoxime derivative of the formula wherein R 1 is (C 1 -C 4 ) alkyl, by heating in a basic medium at a temperature of from 20‹ to 70‹ C., or (b) reacting an α-aminoxy-ester of the general formula or an acid addition salt thereof, with an iminoether salt of the formula wherein HA is a molecule of hydrogen chloride or of fluoboric acid, in a basic organic solvent at a temperature of from 80‹ to 120‹ C., or (c] treating a compound of the formula wherein X is a halogen atom, with an alkali metal hydroxide in aqueous solution at a temperature of from 15‹ to 25‹ C., or (d) reacting an α-halogeno-ester of the general formula wherein Y is a halogen atom, with an amidoxime of the general formula in an aqueous organic solvent in the presence of an alkaline condensation agent at a temperature of from 20‹ to 80‹ C. The novel compounds possess phytohormonal and herbicidal properties. [GB1501589A]