Synthesis and insecticidal activity of N-oxydihydropyrroles: 4-hydroxy-3-mesityl-5,5-dimethyl derivatives with various substituents at the 1-position.
A new series of N-oxydihydropyrrole derivatives was synthesized and evaluated for insecticidal activity against Nilaparvata lugens and Myzus persicae. Various substituents were introduced to the 1-position of the dihydropyrrole ring, and the derivatives obtained exhibited systemic and/or contact insecticidal activity. The structure-activity relationship revealed that small alkyoxy and alkoxyalkoxy groups were more favorable than alkylcarbonyloxy, alkoxycarbonyloxy, or sulfonyloxy groups as substituents at the 1-position.
Ito
Mitsuru
M
Agroscience Research Laboratories, Crop Protection Company, Sankyo Co. Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, Japan. mtitou@yasu.sankyo.co.jp
Okui
Hideshi
H
Nakagawa
Harumi
H
Mio
Shigeru
S
Kinoshita
Ayako
A
Obayashi
Takashi
T
Miura
Takako
T
Nagai
Junko
J
Yokoi
Shinji
S
Ichinose
Reiji
R
Tanaka
Keiji
K
Kodama
Seiichiro
S
Iwasaki
Toshiaki
T
Miyake
Takaaki
T
Takashio
Miho
M
Iwabuchi
Jun
J
D000818:Animals; D001042:Aphids; D001937:Brassica / Q000187:drug effects; D018553:Cucumis sativus / Q000187:drug effects; D006430:Hemiptera; D007306:Insecticides / Q000138:chemical synthesis* / Q000633:toxicity; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012275:Oryza / Q000187:drug effects; D011758:Pyrroles / Q000138:chemical synthesis* / Q000633:toxicity; D012639:Seeds; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D007306:Insecticides; D007659:Ketones; D011758:Pyrroles