Synthesis and insecticidal activity of novel N-oxydihydropyrrole derivatives with a substituted spirocyclohexyl group.
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.
Ito
Mitsuru
M
Agroscience Research Laboratories, Sankyo Agro Co. Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, USA. mtitou@shina.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 / 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
D003510:Cyclohexanes; D007306:Insecticides; D011758:Pyrroles; D013141:Spiro Compounds; C013231:pyrroline