Journal of Agricultural and Food Chemistry, volume 65, issue 36, pages 7865-7873
Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors
Yasumichi Onozaki
1
,
Ryo Horikoshi
1
,
Ikuya Ohno
1
,
Shigeki Kitsuda
1
,
Kathleen Durkin
2
,
T. Suzuki
3
,
Chiaki Asahara
3
,
Natsuko Hiroki
3
,
Rena Komabashiri
3
,
Rikako Shimizu
3
,
Shogo Furutani
4
,
MAKOTO IHARA
4
,
Kazuhiko Matsuda
4
,
Masaaki Mitomi
1
,
Shinzo KAGABU
5
,
Katsuhito Uomoto
1
,
M. Tomizawa
3
1
Agricultural
and Veterinary Research Laboratories, Agricultural and Veterinary
Division, Meiji Seika Pharma Co., Ltd., Yokohama, Kanagawa 222-8567, Japan
|
Publication type: Journal Article
Publication date: 2017-08-28
Q1
Q1
SJR: 1.114
CiteScore: 9.9
Impact factor: 5.7
ISSN: 00218561, 15205118
General Chemistry
General Agricultural and Biological Sciences
Abstract
A novel chemotype insecticide flupyrimin (FLP) [N-[(E)-1-(6-chloro-3-pyridinylmethyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide], discovered by Meiji Seika Pharma, has unique biological properties, including outstanding potency to imidacloprid (IMI)-resistant rice pests together with superior safety toward pollinators. Intriguingly, FLP acts as a nicotinic antagonist in American cockroach neurons, and [3H]FLP binds to the multiple high-affinity binding components in house fly nicotinic acetylcholine (ACh) receptor (nAChR) preparation. One of the [3H]FLP receptors is identical to the IMI receptor, and the alternative is IMI-insensitive subtype. Furthermore, FLP is favorably safe to rats as predicted by the very low affinity to the rat α4β2 nAChR. Structure-activity relationships of FLP analogues in terms of receptor potency, featuring the pyridinylidene and trifluoroacetyl pharmacophores, were examined, thereby establishing the FLP molecular recognition at the Aplysia californica ACh-binding protein, a suitable structural surrogate of the insect nAChR. These FLP pharmacophores account for the excellent receptor affinity, accordingly revealing differences in its binding mechanism from IMI.
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GOST
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Onozaki Y. et al. Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors // Journal of Agricultural and Food Chemistry. 2017. Vol. 65. No. 36. pp. 7865-7873.
GOST all authors (up to 50)
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Onozaki Y., Horikoshi R., Ohno I., Kitsuda S., Durkin K., Suzuki T., Asahara C., Hiroki N., Komabashiri R., Shimizu R., Furutani S., IHARA M., Matsuda K., Mitomi M., KAGABU S., Uomoto K., Tomizawa M. Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors // Journal of Agricultural and Food Chemistry. 2017. Vol. 65. No. 36. pp. 7865-7873.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.jafc.7b02924
UR - https://doi.org/10.1021/acs.jafc.7b02924
TI - Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors
T2 - Journal of Agricultural and Food Chemistry
AU - Onozaki, Yasumichi
AU - Horikoshi, Ryo
AU - Ohno, Ikuya
AU - Kitsuda, Shigeki
AU - Durkin, Kathleen
AU - Suzuki, T.
AU - Asahara, Chiaki
AU - Hiroki, Natsuko
AU - Komabashiri, Rena
AU - Shimizu, Rikako
AU - Furutani, Shogo
AU - IHARA, MAKOTO
AU - Matsuda, Kazuhiko
AU - Mitomi, Masaaki
AU - KAGABU, Shinzo
AU - Uomoto, Katsuhito
AU - Tomizawa, M.
PY - 2017
DA - 2017/08/28
PB - American Chemical Society (ACS)
SP - 7865-7873
IS - 36
VL - 65
SN - 0021-8561
SN - 1520-5118
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Onozaki,
author = {Yasumichi Onozaki and Ryo Horikoshi and Ikuya Ohno and Shigeki Kitsuda and Kathleen Durkin and T. Suzuki and Chiaki Asahara and Natsuko Hiroki and Rena Komabashiri and Rikako Shimizu and Shogo Furutani and MAKOTO IHARA and Kazuhiko Matsuda and Masaaki Mitomi and Shinzo KAGABU and Katsuhito Uomoto and M. Tomizawa},
title = {Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors},
journal = {Journal of Agricultural and Food Chemistry},
year = {2017},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.jafc.7b02924},
number = {36},
pages = {7865--7873},
doi = {10.1021/acs.jafc.7b02924}
}
Cite this
MLA
Copy
Onozaki, Yasumichi, et al. “Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors.” Journal of Agricultural and Food Chemistry, vol. 65, no. 36, Aug. 2017, pp. 7865-7873. https://doi.org/10.1021/acs.jafc.7b02924.