Insecticidal and binding activities of N3-substituted imidacloprid derivatives against the housefly Musca domestica and the alpha-bungarotoxin binding sites of nicotinic acetylcholine receptors.
N3-substituted imidacloprid congeners containing C1-C6 alkyl groups or various analogous groups, and their corresponding nitromethylene analogues, were used in this study. Their insecticidal activity against the housefly, Musca domestica, and their binding activity toward the nicotinic acetylcholine receptor were determined. The insecticidal test was conducted using the synergists piperonyl butoxide and propargyl propyl phenylphosphonate. The binding assay was performed with housefly head membrane preparations using radio-labelled alpha-bungarotoxin. Both insecticidal and binding activities were drastically lowered by the introduction of alkyl/allyl groups at the imidazolidine NH sites of both nitroimino and nitromethylene compounds. The binding activity of N3-substituted nitromethylene analogues was much higher than that of the corresponding nitroimino analogues. However, the insecticidal activity of both series of compounds with a given substituent was nearly identical. The insecticidal activity correlated positively with the binding activity after taking into account the structural difference of the nitroimino and nitromethylene moieties and a structural feature of the N3-substituents.
Nishiwaki
H
H
Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. nhisa@colorado.kais.kyoto-u.ac.jp
Nakagawa
Y
Y
Ueno
T
T
Kagabu
S
S
Nishimura
K
K
D000818:Animals; D001665:Binding Sites / Q000187:drug effects; D001681:Biological Assay; D002038:Bungarotoxins / Q000378:metabolism* / Q000494:pharmacology; D006793:Houseflies / Q000187:drug effects / Q000378:metabolism*; D007093:Imidazoles / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D007457:Iodine Radioisotopes; D007700:Kinetics; D008954:Models, Biological; D015394:Molecular Structure; D000073943:Neonicotinoids; D009574:Nitro Compounds; D010574:Pesticide Synergists / Q000494:pharmacology; D010882:Piperonyl Butoxide / Q000494:pharmacology; D010944:Plants; D011978:Receptors, Nicotinic / Q000378:metabolism*
D002038:Bungarotoxins; D007093:Imidazoles; D007306:Insecticides; D007457:Iodine Radioisotopes; D000073943:Neonicotinoids; D009574:Nitro Compounds; D010574:Pesticide Synergists; D011978:Receptors, Nicotinic; C082359:imidacloprid; D010882:Piperonyl Butoxide