Synthesis and Herbicidal Activity of Novel 3-Alkoxycarbonyl-3-aryl-2,3-dihydro-2-oxo-1H-pyrrole Derivatives

• Published in: Journal of Pesticide Science Vol. 29; no. 4; pp. 339 - 347
• Main Authors: Itoh, Shigeyuki, Kajiwara, Takeshi, Kamiyama, Hideo, Fusaka, Takafumi, Yamato, Seiji, Tanaka, Yasushi
• Format: Journal Article
• Language: English
• Published: Tokyo Pesticide Science Society of Japan 01.01.2004; Japan Science and Technology Agency
• Subjects: 2,3-dihydro-2-oxo-1H-pyrrole; 2-oxo-3-pyrrolin; Biological and medical sciences; Echinochloa oryzicola; Fundamental and applied biological sciences. Psychology; herbicidal activity; Parasitic plants. Weeds; Pesticides; Phytopathology. Animal pests. Plant and forest protection; prodrug; Scirpus juncoides; Weeds; prodrug; Monocotyledones; Echinochloa oryzicola; herbicidal activity; Pesticides; 2-oxo-3-pyrrolin; Herbicide; Gramineae; Angiospermae; Echinochloa; 2,3-dihydro-2-oxo-lH-pyrrole; Spermatophyta; Scirpus juncoides
• ISSN: 1348-589X; 0385-1559; 1349-0923
• DOI: 10.1584/jpestics.29.339

In the course of efforts to find novel compounds with improved crop safety in transplanted rice by the modification of 1-[1-(3,5-dichlorophenyl)-1-methylethyl]-4-methyl-3-phenyl-3-pyrrolin-2-one (1a), which was reported to have excellent herbicidal activity against paddy weeds, 2,3-dihydro-2-oxo-1H-pyrrole derivatives with a quaternary carbon atom having an alkoxycarbonyl group at the α-position of the cyclic amide were synthesized and examined. Among these compounds, methyl 1-[1-(3,5-dichlorophenyl)-1-methylethyl]-2,3-dihydro-4-methyl-2-oxo-3-phenyl-1H-pyrrole-3-carboxylate (2a) was not only active against Echinochloa oryzicola and Scirpus juncoides but also compatible with transplanted rice even in harsh conditions. On the basis of preliminary experimental results, it was thought that 2a would generate the corresponding 2-oxo-3-pyrrolin (1a) through the metabolic degradation of the methoxycarbonyl moiety. © Pesticide Science Society of Japan