Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

Kewei Wang; Xuhong Qian; Jingnan Cui

doi:10.1007/s00706-010-0375-4

Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

Kewei Wang
, Xuhong Qian
, Jingnan Cui^*

^*Corresponding author for this work

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

3 Scopus citations

Abstract

A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.

Original language	English
Pages (from-to)	1117-1122
Number of pages	6
Journal	Monatshefte fur Chemie
Volume	141
Issue number	10
DOIs	https://doi.org/10.1007/s00706-010-0375-4
State	Published - Oct 2010
Externally published	Yes

Keywords

(E)-configuration
Insecticides
Neonicotinoids
Nitrovinyl compound
X-ray analysis

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10.1007/s00706-010-0375-4

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title = "Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides",

abstract = "A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35\% overall yields. All compounds were structurally characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.",

keywords = "(E)-configuration, Insecticides, Neonicotinoids, Nitrovinyl compound, X-ray analysis",

author = "Kewei Wang and Xuhong Qian and Jingnan Cui",

year = "2010",

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doi = "10.1007/s00706-010-0375-4",

language = "英语",

volume = "141",

pages = "1117--1122",

journal = "Monatshefte fur Chemie",

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TY - JOUR

T1 - Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

AU - Wang, Kewei

AU - Qian, Xuhong

AU - Cui, Jingnan

PY - 2010/10

Y1 - 2010/10

N2 - A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.

AB - A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.

KW - (E)-configuration

KW - Insecticides

KW - Neonicotinoids

KW - Nitrovinyl compound

KW - X-ray analysis

UR - https://www.scopus.com/pages/publications/78651097803

U2 - 10.1007/s00706-010-0375-4

DO - 10.1007/s00706-010-0375-4

M3 - 文章

AN - SCOPUS:78651097803

SN - 0026-9247

VL - 141

SP - 1117

EP - 1122

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 10

ER -

Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

Abstract

Keywords

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