3,4-Dihydro-1,2,4-triazine compounds
AssigneeBayer Aktiengesellschaft
InventorsWilfried Draber, Helmut Timmler, Ludwig Eue, Robert R. Schmidt
Life of this patent
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Abstract
Novel 3,4-dihydro-1,2,4-triazine compounds of the formula ##SPC1## In which R.sup.1 is alkyl or cycloalkyl; R.sup.2 is methyl, amino, alkylideneamino, methylamino, .beta.-hydroxyethylamino, 2-furylmethylamino, aralkylamino or substituted aralkylamino; and R.sup.3 is alkyl, aryl or substituted aryl; Are prepared by reacting the corresponding 1,2,4-triazin-5-one with sodium borohydride in the presence of a polar solvent at a temperature between -10.degree. and +25.degree.C. The novel compounds are outstandingly effective as herbicides and display particularly selective action.
Claims20
3,4-Dihydro-1,2,4-triazine compound of the formula ##SPC13##
- wherein
- R.sup.1 is alkyl of up to six carbon atoms or cycloalkyl of from three to six carbon atoms;
- R.sup.2 is methyl, amino, alkylideneamino, methylamino, .beta.-hydroxyethylamino, 2-furylmethylamino, aralkylamino of up to 12 carbon atoms or substituted aralkylamino of up to 12 carbon atoms wherein the substituents are selected from lower alkyl;
- and
- R.sup.3 is alkyl of up to four carbon atoms or aryl of up to 10 carbon atoms or substituted aryl of up to 10 carbon atoms in the aryl moiety wherein the substituents are selected from alkyl of from one to four carbon atoms, halogen, haloalkyl, nitro and phenoxy.
Process for preparing a 3,4-dihydro-1,2,4-triazine compound of the formula ##SPC14##
- wherein
- R.sup.1 is alkyl of up to six carbon atoms or cycloalkyl of from three to six carbon atoms;
- R.sup.2 is methyl, amino, alkylideneamino, methylamino, .beta.-hydroxyethylamino, 2-furylmethylamino, aralkylamino of up to 12 carbon atoms or substituted aralkylamino of up to 12 carbon atoms wherein the substituents are selected from lower alkyl;
- and
- R.sup.3 is alkyl of up to four carbon atoms or aryl of up to 10 carbon atoms or substituted aryl of up to 10 carbon atoms in the aryl moiety wherein the substituents are selected from alkyl of from one to four carbon atoms, halogen, haloalkyl, nitro and phenoxy;
- which process comprises reducing a 1,2,4-triazine-5-one compound of the formula ##SPC15##
- wherein
- R.sup.1, r.sup.2 and R.sup.3 are defined as above
- with sodium borohydride in the presence of a polar solvent at a temperature from -10.degree.C to 25.degree.C.
Dependencies are inferred from the claim text.