Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities

Xusheng Shao; F. U. Hua; X. U. Xiaoyong; X. U. Xinglei; L. I.U. Zewen; L. I. Zhong; Xuhong Qian

doi:10.1021/jf902531y

Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities

Xusheng Shao, F. U. Hua, X. U. Xiaoyong, X. U. Xinglei, L. I.U. Zewen, L. I. Zhong, Xuhong Qian

Research output: Contribution to journal › Article › peer-review

125 Scopus citations

Abstract

A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by ¹H NMR, ¹³C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nllaparvata lugens). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.

Original language	English
Pages (from-to)	2696-2702
Number of pages	7
Journal	Journal of Agricultural and Food Chemistry
Volume	58
Issue number	5
DOIs	https://doi.org/10.1021/jf902531y
State	Published - 10 Mar 2010
Externally published	Yes

Keywords

Dialdehydes
Imidacloprid
Insecticide
Neonicotinoids
Oxabridge

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10.1021/jf902531y

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Shao, X., Hua, F. U., Xiaoyong, X. U., Xinglei, X. U., Zewen, L. I. U., Zhong, L. I., & Qian, X. (2010). Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities. Journal of Agricultural and Food Chemistry, 58(5), 2696-2702. https://doi.org/10.1021/jf902531y

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title = "Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities",

abstract = "A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by 1H NMR, 13C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nllaparvata lugens). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.",

keywords = "Dialdehydes, Imidacloprid, Insecticide, Neonicotinoids, Oxabridge",

author = "Xusheng Shao and Hua, \{F. U.\} and Xiaoyong, \{X. U.\} and Xinglei, \{X. U.\} and Zewen, \{L. I.U.\} and Zhong, \{L. I.\} and Xuhong Qian",

year = "2010",

month = mar,

day = "10",

doi = "10.1021/jf902531y",

language = "英语",

volume = "58",

pages = "2696--2702",

journal = "Journal of Agricultural and Food Chemistry",

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publisher = "American Chemical Society",

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Shao, X, Hua, FU, Xiaoyong, XU, Xinglei, XU, Zewen, LIU, Zhong, LI & Qian, X 2010, 'Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities', Journal of Agricultural and Food Chemistry, vol. 58, no. 5, pp. 2696-2702. https://doi.org/10.1021/jf902531y

Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities. / Shao, Xusheng; Hua, F. U.; Xiaoyong, X. U. et al.
In: Journal of Agricultural and Food Chemistry, Vol. 58, No. 5, 10.03.2010, p. 2696-2702.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid

T2 - Design, synthesis, crystal structure, and insecticidal activities

AU - Shao, Xusheng

AU - Hua, F. U.

AU - Xiaoyong, X. U.

AU - Xinglei, X. U.

AU - Zewen, L. I.U.

AU - Zhong, L. I.

AU - Qian, Xuhong

PY - 2010/3/10

Y1 - 2010/3/10

N2 - A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by 1H NMR, 13C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nllaparvata lugens). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.

AB - A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by 1H NMR, 13C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nllaparvata lugens). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.

KW - Dialdehydes

KW - Imidacloprid

KW - Insecticide

KW - Neonicotinoids

KW - Oxabridge

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AN - SCOPUS:77949371596

SN - 0021-8561

VL - 58

SP - 2696

EP - 2702

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 5

ER -

Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities

Abstract

Keywords

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