method for the preparation of herbicidepreparaten by 1,2,4 - 3,5-triazine - 5 - off in a suitable form for such preparations, and methods for the preparation of 1.2.4 - 5 - off 3,5-triazine suitable for use in the method and procedure for the control of weeds in application of these preparations.

摘要

1331739 4 - Amino -1,2,4 - triazine - 5 - ones BAYER AG 17 Feb 1972 [18 Feb 1971] 7434/72 Heading C2C The invention comprises 4-amino-1,2,4-triazine-5-ones of general Formula (I) wherein R 1 and R 4 which may be the same or different, are -H, -CF 3 , C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, halophenyl, C 1-4 alkyl. phenyl, C 1-4 alkoxyphenyl, or phenyl-(C 1-3 )-alkyl; R 2 is -H or C 1-4 alkyl; and R 3 is -H, C 1-4 alkyl, C 1-4 haloalkyl, phenyl, phenyl-(C 1-3 )- alkyl, C 1-4 alkylphenyl, C 1-4 alkoxyphenyl or C 1-4 alkylmercaptophenyl. The compounds of Formula (I) are prepared by reacting a glyoxylic acid ester 2-acylhydrazone of Formula (II), R 1 -CO-NH-N=C(R 4 )-COOR, wherein R is C 1-4 alkyl, with a hydrazine derivative of general Formula (III), H 2 N-NR 2 R 3 , in the presence of an organic solvent (e.g. pyridine) and preferably at 50-150‹ C. in the presence of a basic catalyst (e.g. KOH, NaOH, KOt-Bu, N(C 2 H 5 ) 3 , C 6 H 5 CH 2 N(CH 3 ) 2 or N-methyl-morpholine). The reactants of Formulµ (II) and (III) are preferably used in a molar ratio of 1 : 1 to 1 : 2, respectively. The invention also comprises a herbicidal composition containing as active ingredient a compound of Formula (I) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface active agent. Combating weeds by application thereto or to a habitat thereof of a compound of Formula (I) or a composition containing the same is also envisaged. The compounds of Formula (II) may be prepared by reacting a glyoxylic acid ester of formula R 4 -CO-COOR with an acylhydrazine of formula R 1 -CO-NH-NH 2 in the presence of an organic solvent and an acid catalyst. Examples (1-3) describe the preparation of compounds of Formulµ (I) and (II) wherein R 2 and R 3 are hydrogen atoms and R 1 and R 4 are variously -H, alkyl, cycloalkyl and phenyl. Many more compounds are specifically referred to in the description.