Asymmetric chloronicotinyl insecticide, 1-[1-(6-chloro-3-pyridyl)ethyl]-2-nitroiminoimidazolidine: preparation, resolution and biological activities toward insects and their nerve preparations.
The asymmetric chloronicotinyl insecticide, 1-[1-(6-chloro-3-pyridyl)ethyl]-2-nitroiminoimidazolidine, was prepared, and the absolute configurations of the enantiomers were determined by an X-ray analysis. The insecticidal activity against the housefly measured with metabolic inhibitors showed the (S) enantiomer to be slightly more active than the (R) isomer. Electrophysiological measurements on the American cockroach central nerve cord showed the compounds to elicite the impulses and subsequently blocked them. The neuroblocking potency of the (S) isomer was 5.9 microM, while that of the (R) isomer was as high as 73 microM. The molar concentrations required for 50% inhibition of the specific binding of [3H]imidacloprid to the housefly head membrane preparation were respectively 0.19 microM and 0.95 microM for the (S) and (R) isomers. This enatioselectivity ratio was smaller than 35 for nicotine isomers but greater than 2 for epibatidine isomers.
Kagabu
Shinzo
S
Department of Chemistry, Faculty of Education, Gifu University, Gifu 501-1193, Japan. kagabus@cc.gifu-u.ac.jp
Kiriyama
Kazuhisa
K
Nishiwaki
Hisashi
H
Kumamoto
Yuko
Y
Tada
Toshiji
T
Nishimura
Keiichiro
K
D000818:Animals; D001665:Binding Sites; D003058:Cockroaches / Q000502:physiology*; D018360:Crystallography, X-Ray; D006793:Houseflies / Q000502:physiology*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D048289:Imidazolidines; D007202:Indicators and Reagents; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D000073943:Neonicotinoids; D009420:Nervous System / Q000187:drug effects*; D009474:Neurons / Q000187:drug effects; D009574:Nitro Compounds; D010944:Plants; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011950:Receptors, Cholinergic / Q000187:drug effects
C481445:1-(1-(6-chloro-3-pyridyl)ethyl)-2-nitroiminoimidazolidine; D007093:Imidazoles; D048289:Imidazolidines; D007202:Indicators and Reagents; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; D011725:Pyridines; D011950:Receptors, Cholinergic; C082359:imidacloprid