PURPOSE: To obtain the subject compound by reacting a propiolic acid ester with a primary amine in a mixed solvent containing water and a hydrophilic solvent in a specific proportion, providing an N-substituted-propiolamide in high yield and selectivity and then reacting the resultant compound with an iodinating agent.
CONSTITUTION: This method for producing an N-substituted-3-iodopropiolamide expressed by formula IV (R2 is an alkyl) is to react a propiolic acid ester expressed by formula I (R1 is an alkyl) with a primary amine expressed by formula II in a mixed solvent of water/hydrophilic solvent at (1.5-10)/1 volume ratio of the water to the hydrophilic solvent, provide an N-substituted-propiolamide expressed by formula III and then react the resultant N-substituted-propiolamide expressed by formula III with an iodinating agent. An alcohol is preferred as the hydrophilic solvent. The compound expressed by formula I is obtained by esterifying propiolic acid. The steps for successively obtaining the compounds expressed by formulas I to IV from the propiolic acid are preferably carried out according to continuous reactions. The compound expressed by formula IV is capable of manifesting high antimicrobial activities and useful as a pest controlling agent.
MATSUMOTO SEIJI
MIWA KATSUHIKO
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