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Synthesis and Herbicidal Activity of New Imidazolidinedione Derivatives
Tomoyuki YANO, Natsuko OKANO, Sadayuki UGAI, Masahiro HORI and Kenji HIRAI
J. Pestic. Sci.
26, 67-75 (2001)
A series of new 3-(5-alkoxy-2,4-dihalophenyl)-5-alkylidene-1,3-imidazolidine-2,4-dione derivatives was synthesized and their herbicidal activities against various weeds were examined. The herbicidal activities varied with the substituents on the benzene ring and the compounds having a 5-alkynyloxy-4-chloro-2-fluorophenyl group exhibited relatively higher herbicidal activities. In the case of monocyclic imidazolidinedione derivatives, introduction of an isopropylidene group at the 5-position and a lower alkyl group at the 1-position of the imidazolidinedione ring was most effective in enhancing the activity. In the case of bicyclic imidazolidinedione derivatives, 5,6-dihydroimidazo[1,5-a]pyridine derivatives gave a higher selectivity than tetrahydroimidazo[1,5-a]pyridine derivatives, therefore, it was thought that the presence of a double bond was important for the crop safety. Among the compounds synthesized, a bicyclic imidazolidinedione compound, 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-5,6-dihydroimidazo[1,5-a]pyridine-1,3[2H,7H]-dione is considered to be the most promising candidate as a corn herbicide.
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