PURPOSE: To obtain the subject new derivative, a halogenated cycloalkenecarboxylic acid compound having a nitrogen-containing heterocyclic group bonded by sulfide group, useful for herbicide, etc., having a wide herbicidal spectrum, high herbicidal effects and excellent safety to crops.
CONSTITUTION: A halogenated cycloalkanone derivative (e.g. ethyl 1-fluoro-2- mercapto-2-cyclohexanecarboxylate) of formula I [W is halogen; X is lower alkoxy, lower alkenoxy, (substituted) aryloxy, hydroxy, amino, etc.; (n) is 0 or 1] is reacted with a compound (e.g. 4-chloro-6-methoxy-2- methylsulfonylpyrimidine) of formula II (W' is halogen, alkylsulfonyl, etc.; Y and Z are N or methine; R1 and R2 are halogen, lower alkyl, lower alkoxy, etc.) in a solventless state or in the presence of a proper solvent by using a proper base in the temperature range of -78°C to the boiling point of the solvent to give the objective compound of formula III.
KUDO SACHIO
KUMAMOTO YORIO
ENDO KEIJI
KAWAGUCHI SHINJI
HIGURE RIKA
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