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Nicotinic acetylcholine receptor binding of imidacloprid‐related diaza compounds with various ring sizes and their insecticidal activity against Musca domestica
Author(s) -
Kagabu Shinzo,
Nishiwaki Hisashi,
Sato Kazuyuki,
Hibi Manabu,
Yamaoka Nahato,
Nakagawa Yoshiaki
Publication year - 2002
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.488
Subject(s) - piperonyl butoxide , imidazolidine , chemistry , ring (chemistry) , stereochemistry , in vivo , imidacloprid , ring size , acetylcholine receptor , nicotinic agonist , in vitro , biochemistry , receptor , biology , toxicity , pesticide , organic chemistry , microbiology and biotechnology , agronomy
Fifteen 5‐substituted 1‐(6‐chloro‐3‐pyridylmethyl)‐2‐nitromethylene‐1,3‐diazacyclohexanes and three other related compounds having a five‐ or seven‐membered ring were synthesized and their biological activities were measured in vivo and in vitro . The insecticidal ( in vivo ) activity was evaluated against houseflies Musca domestica L under synergistic conditions with propargyl propyl phenyl phosphonate and piperonyl butoxide. The binding activity of each compound to nicotinic acetylcholine receptor in vitro was measured using [ 125 I]α‐bungarotoxin. The insecticidal activities of the unsubstituted diazacyclohexane analogues were slightly higher than those of the imidazolidine analogues, but the enlargement of ring size to diazacycloheptane lowered the activity. Substitution of 1,3‐diazacyclohexane or imidazolidine rings was not generally favourable for the activity, but the unsubstituted 1,3‐diazacyclohexane analogue showed the highest binding activity. Ring substitutions and ring enlargement decreased the activity 100–30 000‐fold. © 2002 Society of Chemical Industry