NEW MATERIAL:The title compound of formula I [X is Br or Cl; Y is (substituted) hydrazino, semicarbazido or thiosemicarbazido group].
EXAMPLE: 2'-Fluoro-4'-chloro-2-n-butyrolhydrazoyl-cyclohexenecarbanilide.
USE: A heribicide having a great herbicidal activity against a wide range of monocotyledonous or dioctyledonous weeds in soil or foliar treatment, with low toxicity to mammals and fishes, and safely usable as an agricultural chemical.
PROCESS: A compound of formula II is reacted with a compound of the formula Y.H, e.g. hydrogen halide, in an inert solvent, e.g. benzene, at about 5W60°C for about 5minW10hr, and the reaction mixture is concentrated by the well-known method to give the compound of formula I. The amount of the compound Y.H is 0.8W several moles, preferably 0.9W1.2mol, per mole of the compound of formula II.
AOKI ISAO