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

Hide authors affiliations Show authors affiliations: 5 affiliations

Agricultural and Veterinary Research Laboratories, Agricultural and Veterinary Division, Meiji Seika Pharma Co., Ltd., Yokohama, Kanagawa 222-8567, Japan |

College of Chemistry, University of California, Berkeley, California 94720-1460, United States |

Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan |

⁴

Faculty of Agriculture, Kindai University, Nara 631-8505, Japan |

⁵

Faculty of Education, Gifu University, Gifu 501-1193, Japan |

Publication type: Journal Article

Publication date: 2017-08-28

American Chemical Society (ACS)

Journal: Journal of Agricultural and Food Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 6.1

ISSN: 00218561, 15205118

DOI: 10.1021/acs.jafc.7b02924

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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.

By date By citations

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Citations by journals

	2 4 6 8 10 12
Journal of Agricultural and Food Chemistry	Journal of Agricultural and Food Chemistry, 11, 27.5% Journal of Agricultural and Food Chemistry 11 publications, 27.5%
Pesticide Biochemistry and Physiology	Pesticide Biochemistry and Physiology, 4, 10% Pesticide Biochemistry and Physiology 4 publications, 10%
Pest Management Science	Pest Management Science, 4, 10% Pest Management Science 4 publications, 10%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 3, 7.5% European Journal of Organic Chemistry 3 publications, 7.5%
Molecules	Molecules, 2, 5% Molecules 2 publications, 5%
Journal of Pesticide Sciences	Journal of Pesticide Sciences, 1, 2.5% Journal of Pesticide Sciences 1 publication, 2.5%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 1, 2.5% Chinese Journal of Organic Chemistry 1 publication, 2.5%
Journal of Chemical Research	Journal of Chemical Research, 1, 2.5% Journal of Chemical Research 1 publication, 2.5%
Crystals	Crystals, 1, 2.5% Crystals 1 publication, 2.5%
International Journal of Molecular Sciences	International Journal of Molecular Sciences, 1, 2.5% International Journal of Molecular Sciences 1 publication, 2.5%
Frontiers in Chemistry	Frontiers in Chemistry, 1, 2.5% Frontiers in Chemistry 1 publication, 2.5%
Molecular Diversity	Molecular Diversity, 1, 2.5% Molecular Diversity 1 publication, 2.5%
Environmental Pollution	Environmental Pollution, 1, 2.5% Environmental Pollution 1 publication, 2.5%
Chemosphere	Chemosphere, 1, 2.5% Chemosphere 1 publication, 2.5%
Chinese Chemical Letters	Chinese Chemical Letters, 1, 2.5% Chinese Chemical Letters 1 publication, 2.5%
Journal of Molecular Graphics and Modelling	Journal of Molecular Graphics and Modelling, 1, 2.5% Journal of Molecular Graphics and Modelling 1 publication, 2.5%
Tetrahedron	Tetrahedron, 1, 2.5% Tetrahedron 1 publication, 2.5%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 2.5% Bioorganic and Medicinal Chemistry 1 publication, 2.5%
Current Opinion in Insect Science	Current Opinion in Insect Science, 1, 2.5% Current Opinion in Insect Science 1 publication, 2.5%
Journal of Heterocyclic Chemistry	Journal of Heterocyclic Chemistry, 1, 2.5% Journal of Heterocyclic Chemistry 1 publication, 2.5%
Journal of Medicinal Chemistry	Journal of Medicinal Chemistry, 1, 2.5% Journal of Medicinal Chemistry 1 publication, 2.5%
	2 4 6 8 10 12

Citations by publishers

	2 4 6 8 10 12
American Chemical Society (ACS)	American Chemical Society (ACS), 12, 30% American Chemical Society (ACS) 12 publications, 30%
Elsevier	Elsevier, 11, 27.5% Elsevier 11 publications, 27.5%
Wiley	Wiley, 8, 20% Wiley 8 publications, 20%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 4, 10% Multidisciplinary Digital Publishing Institute (MDPI) 4 publications, 10%
Pesticide Science Society of Japan/Nippon Noyaku Gakkai	Pesticide Science Society of Japan/Nippon Noyaku Gakkai, 1, 2.5% Pesticide Science Society of Japan/Nippon Noyaku Gakkai 1 publication, 2.5%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 2.5% Shanghai Institute of Organic Chemistry 1 publication, 2.5%
SAGE	SAGE, 1, 2.5% SAGE 1 publication, 2.5%
Frontiers Media S.A.	Frontiers Media S.A., 1, 2.5% Frontiers Media S.A. 1 publication, 2.5%
Springer Nature	Springer Nature, 1, 2.5% Springer Nature 1 publication, 2.5%
	2 4 6 8 10 12

We do not take into account publications without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
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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) Copy

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.

RIS |

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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 - Asahara, Chiaki

AU - Hiroki, Natsuko

AU - Komabashiri, Rena

AU - Shimizu, Rikako

AU - Furutani, Shogo

AU - Mitomi, Masaaki

AU - KAGABU, Shinzo

AU - Uomoto, Katsuhito

AU - Tomizawa, M.

AU - Durkin, Kathleen

AU - Suzuki, T.

AU - IHARA, MAKOTO

AU - Matsuda, Kazuhiko

PY - 2017

DA - 2017/08/28 00:00:00

PB - American Chemical Society (ACS)

SP - 7865-7873

IS - 36

VL - 65

SN - 0021-8561

SN - 1520-5118

ER -

BibTex |

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BibTex Copy

@article{2017_Onozaki,

author = {Yasumichi Onozaki and Ryo Horikoshi and Ikuya Ohno and Shigeki Kitsuda and Chiaki Asahara and Natsuko Hiroki and Rena Komabashiri and Rikako Shimizu and Shogo Furutani and Masaaki Mitomi and Shinzo KAGABU and Katsuhito Uomoto and M. Tomizawa and Kathleen Durkin and T. Suzuki and MAKOTO IHARA and Kazuhiko Matsuda},

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}

}

MLA

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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.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Journal of Agricultural and Food Chemistry

Quartile SCImago

Quartile WOS

Impact factor

6.1

ISSN

00218561 (Print)
15205118 (Electronic)