title: Synthesis and insecticidal activity of novel N-oxydihydropyrrole derivatives with a substituted spirocyclohexyl group.
abstract: A series of 5-spirocyclohexyl-3-(2,6-dimethylphenyl)-1,5-dihydro-2H-pyrrol-2-one derivatives (3) with various substituents on the spirocyclohexyl ring was synthesized and evaluated for its insecticidal activity against the aphid, Myzus persicae. Substituents at the 1- and 4-positions of the dihydropyrrole ring were also varied to optimize the activity. An investigation of the structure-activity relationship revealed that methoxy, alkoxyalkoxy, ethylenedioxy and methoxyimino groups were favorable as substituents at the 4-position of the spirocyclohexyl ring. The activity was optimized by the respective substitution of a methoxy or methoxymethoxy moiety and cyclopropylcarbonyloxy group at the 1- and 4-positions of the dihydropyrrole ring.
authors.affiliation: Agroscience Research Laboratories, Sankyo Agro Co. Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, USA. mtitou@shina.sankyo.co.jp
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Ito
authors.forename: Hideshi
authors.initials: H
authors.lastname: Okui
authors.forename: Harumi
authors.initials: H
authors.lastname: Nakagawa
authors.forename: Shigeru
authors.initials: S
authors.lastname: Mio
authors.forename: Ayako
authors.initials: A
authors.lastname: Kinoshita
authors.forename: Takashi
authors.initials: T
authors.lastname: Obayashi
authors.forename: Takako
authors.initials: T
authors.lastname: Miura
authors.forename: Junko
authors.initials: J
authors.lastname: Nagai
authors.forename: Shinji
authors.initials: S
authors.lastname: Yokoi
authors.forename: Reiji
authors.initials: R
authors.lastname: Ichinose
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanaka
authors.forename: Seiichiro
authors.initials: S
authors.lastname: Kodama
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Iwasaki
authors.forename: Takaaki
authors.initials: T
authors.lastname: Miyake
authors.forename: Miho
authors.initials: M
authors.lastname: Takashio
authors.forename: Jun
authors.initials: J
authors.lastname: Iwabuchi
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D003510:Cyclohexanes; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D013141:Spiro Compounds; D013329:Structure-Activity Relationship
chemical_list: D003510:Cyclohexanes; D007306:Insecticides; D011758:Pyrroles; D013141:Spiro Compounds; C013231:pyrroline