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The insecticidal activity and action mode of an imidacloprid analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine.
Insect Sci. 2016 Oct; 23(5):688-94.IS

Abstract

Neonicotinoids, such as imidacloprid, are key insecticides extensively used for control of Nilaparvata lugens. However, imidacloprid resistance has been reported in many Asian countries in recent years. To understand the roles of the chlorine atom of pyridyl group on insecticidal activity and resistance, the atom was removed to generate an imidacloprid analogue DC-Imi (DesChlorine Imidacloprid). DC-Imi showed significantly higher toxicity than imidacloprid in the susceptible strain of N. lugens, but had medium level cross-resistance in an imidacloprid-resistant strain. In Xenopus oocyte expressed nicotinic acetylcholine receptors (nAChRs) Nlα1/rβ2, the inward currents evoked by DC-Imi were detected and could be blocked by typical nAChRs antagonist dihydro-β-erythroidine (DHβE), which demonstrated that DC-Imi acted as an agonist on insect nAChRs. The efficacy of DC-Imi on Nlα1/rβ2 was 1.8-fold higher than that of imidacloprid. In addition, the influence of an imidacloprid resistance associated mutation (Y151S) on agonist potencies was evaluated. Compared with the wild-type receptor, the mutation reduced maximal inward current of DC-Imi to 55.6% and increased half maximal effective concentration (EC50) to 3.53-fold. Compared with imidacloprid (increasing EC50 to 2.38-fold of wild-type receptor), Y151S mutation decreased DC-Imi potency more significantly. The results indicated that the selective and possibly high toxicities could be achieved through the modification of 6-chloro-3-pyridyl group in imidacloprid and other neonicotinoids.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhuang AX
Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, Nanjing, China.
Zhang YX
Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, Nanjing, China.
Zhang H
Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, Nanjing, China.
Liu ZW
Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, Nanjing, China. liuzewen@njau.edu.cn.

MeSH

AnimalsDihydro-beta-ErythroidineHemipteraImidazolesInsecticide ResistanceInsecticidesMutationNicotinic AntagonistsNitro CompoundsNymphOocytesReceptors, NicotinicXenopus

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25755197

Citation

Zhuang, An-Xiang, et al. "The Insecticidal Activity and Action Mode of an Imidacloprid Analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine." Insect Science, vol. 23, no. 5, 2016, pp. 688-94.
Zhuang AX, Zhang YX, Zhang H, et al. The insecticidal activity and action mode of an imidacloprid analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine. Insect Sci. 2016;23(5):688-94.
Zhuang, A. X., Zhang, Y. X., Zhang, H., & Liu, Z. W. (2016). The insecticidal activity and action mode of an imidacloprid analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine. Insect Science, 23(5), 688-94. https://doi.org/10.1111/1744-7917.12217
Zhuang AX, et al. The Insecticidal Activity and Action Mode of an Imidacloprid Analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine. Insect Sci. 2016;23(5):688-94. PubMed PMID: 25755197.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The insecticidal activity and action mode of an imidacloprid analogue, 1-(3-pyridylmethyl)-2-nitroimino-imidazolidine. AU - Zhuang,An-Xiang, AU - Zhang,Yi-Xi, AU - Zhang,Hui, AU - Liu,Ze-Wen, Y1 - 2015/05/19/ PY - 2015/02/05/accepted PY - 2015/3/11/entrez PY - 2015/3/11/pubmed PY - 2017/4/30/medline KW - Nilaparvata lugens KW - Y151S mutation KW - imidacloprid analogue KW - insecticide activity KW - nicotinic acetylcholine receptors SP - 688 EP - 94 JF - Insect science JO - Insect Sci VL - 23 IS - 5 N2 - Neonicotinoids, such as imidacloprid, are key insecticides extensively used for control of Nilaparvata lugens. However, imidacloprid resistance has been reported in many Asian countries in recent years. To understand the roles of the chlorine atom of pyridyl group on insecticidal activity and resistance, the atom was removed to generate an imidacloprid analogue DC-Imi (DesChlorine Imidacloprid). DC-Imi showed significantly higher toxicity than imidacloprid in the susceptible strain of N. lugens, but had medium level cross-resistance in an imidacloprid-resistant strain. In Xenopus oocyte expressed nicotinic acetylcholine receptors (nAChRs) Nlα1/rβ2, the inward currents evoked by DC-Imi were detected and could be blocked by typical nAChRs antagonist dihydro-β-erythroidine (DHβE), which demonstrated that DC-Imi acted as an agonist on insect nAChRs. The efficacy of DC-Imi on Nlα1/rβ2 was 1.8-fold higher than that of imidacloprid. In addition, the influence of an imidacloprid resistance associated mutation (Y151S) on agonist potencies was evaluated. Compared with the wild-type receptor, the mutation reduced maximal inward current of DC-Imi to 55.6% and increased half maximal effective concentration (EC50) to 3.53-fold. Compared with imidacloprid (increasing EC50 to 2.38-fold of wild-type receptor), Y151S mutation decreased DC-Imi potency more significantly. The results indicated that the selective and possibly high toxicities could be achieved through the modification of 6-chloro-3-pyridyl group in imidacloprid and other neonicotinoids. SN - 1744-7917 UR - https://www.unboundmedicine.com/medline/citation/25755197/The_insecticidal_activity_and_action_mode_of_an_imidacloprid_analogue_1__3_pyridylmethyl__2_nitroimino_imidazolidine_ DB - PRIME DP - Unbound Medicine ER -