Sulfoxaflor and the sulfoximine insecticides: Chemistry, mode of action and basis for efficacy on resistant insects

Sparks, Thomas C.; Watson, Gerald B.; Loso, Michael R.; Geng, Chaoxian; Babcock, Jon; Thomas, James D.

doi:10.1016/j.pestbp.2013.05.014

Cited by 308 publications

(194 citation statements)

References 26 publications

Supporting

Mentioning

181

Contrasting

Unclassified

Order By: Relevance

“…Metabolites of flupyradifurone include the 6-chloronicotinic acid (6-CNA), common to most neonicotinoids. A very similar situation is observed for sulfoxaflor, introduced as a sulfoximine insecticide by the manufacturer (Sparks et al 2013). As can be seen in Fig.…”

Section: Mode Of Action and Metabolismsupporting

confidence: 77%

An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 1: new molecules, metabolism, fate, and transport

Giorio

Safer

Sánchez‐Bayo

et al. 2017

Environ Sci Pollut Res

View full text Add to dashboard Cite

With the exponential number of published data on neonicotinoids and fipronil during the last decade, an updated review of literature has been conducted in three parts. The present part focuses on gaps of knowledge that have been addressed after publication of the Worldwide Integrated Assessment (WIA) on systemic insecticides in 2015. More specifically, new data on the mode of action and metabolism of neonicotinoids and fipronil, and their toxicity to invertebrates and vertebrates, were obtained. We included the newly detected synergistic effects and/or interactions of these systemic insecticides with other insecticides, fungicides, herbicides, adjuvants, honeybee viruses, and parasites of honeybees. New studies have also investigated the contamination of all environmental compartments (air and dust, soil, water, sediments, and plants) as well as bees and apicultural products, food and beverages, and the exposure of invertebrates and vertebrates to such contaminants. Finally, we review new publications on remediation of neonicotinoids and fipronil, especially in water systems. Conclusions of the previous WIA in 2015 are reinforced; neonicotinoids and fipronil represent a major threat worldwide for biodiversity, ecosystems, and all the services the latter provide.

show abstract

Section: Mode Of Action and Metabolismsupporting

confidence: 77%

An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 1: new molecules, metabolism, fate, and transport

Giorio

Safer

Sánchez‐Bayo

et al. 2017

Environ Sci Pollut Res

View full text Add to dashboard Cite

show abstract

“…8 However, there is no literature available on analytical methods for the determination of sulfoxaflor residues in foods of animal origin. 9 Animal matrices are considerably complicated as they are rich in fat, protein, and some other lipophilic compounds that are easily coextracted with the target analytes. 10 Thus, it is extremely difficult to effectively purify the samples.…”

Section: ■ Introductionmentioning

confidence: 99%

Determination of Sulfoxaflor in Animal Origin Foods Using Dispersive Solid-Phase Extraction and Multiplug Filtration Cleanup Method Based on Multiwalled Carbon Nanotubes by Ultraperformance Liquid Chromatography/Tandem Mass Spectrometry

Tian

Dong

et al. 2016

J. Agric. Food Chem.

View full text Add to dashboard Cite

In the present study, a rapid analytical method was developed to determine the residue of sulfoxaflor in milk, pork, eggs, porcine liver, porcine kidney, porcine fat, and chicken. The dispersive solid-phase extraction (d-SPE) and multiplug filtration cleanup (m-PFC) based on multiwalled carbon nanotubes (MWCNTs) were compared for sulfoxaflor in the above matrix and then detected by ultraperformance liquid chromatography coupled with tandem mass spectrometry. The analyte was eluted within 5 min using a Waters Acquity UHPLC HSS T3 column under ESI(+) conditions. The limits of detection were 1 μg kg(-1) for all of the matrices. Good linearities of sulfoxaflor were obtained in the range of 1-100 μg L(-1), and the correlation coefficients (R(2)) were higher than 0.9988 in all matrices. The average recoveries of the target compound were between 75.5% and 114.9%, and the intraday and interday relative standard deviation values were <14%. Both methods have purification ability. While considering the cost of analysis and the applicability of the method, d-SPE was selected to purify the samples in the present study. The method was successfully used to analyze the residue of sulfoxaflor in foods of animal origin.

show abstract

“…[16,17] The insecticidal mechanism of sulfoxaflor is reliant on the agonistic action towards the insect nicotinic acetylcholine receptor (nAChR). [18][19][20][21] The effects of sulfoxaflor on the insects include excitatory symptoms, such as tremors, followed by paralysis and mortality, thereby suggesting that the molecule acts on the insect nervous system. [19] Recent studies have reported that the sulfoximine structure can improve the insecticidal activities of anthranilic diamides.…”

Section: Introductionmentioning

confidence: 99%

Novel Anthranilic Diamide Insecticides: Design, Synthesis, and Insecticidal Evaluation

Hua¹,

Mao²,

Fan³

et al. 2014

Aust. J. Chem.

View full text Add to dashboard Cite

Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1 H and 13 C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of compoundBioassay results indicated that most of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the positive control cyantraniliprole. In particular, N- (2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100 % at a concentration of 1 mg mL À1 . These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.

show abstract

Sulfoxaflor and the sulfoximine insecticides: Chemistry, mode of action and basis for efficacy on resistant insects

Cited by 308 publications

References 26 publications

An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 1: new molecules, metabolism, fate, and transport

An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 1: new molecules, metabolism, fate, and transport

Determination of Sulfoxaflor in Animal Origin Foods Using Dispersive Solid-Phase Extraction and Multiplug Filtration Cleanup Method Based on Multiwalled Carbon Nanotubes by Ultraperformance Liquid Chromatography/Tandem Mass Spectrometry

Novel Anthranilic Diamide Insecticides: Design, Synthesis, and Insecticidal Evaluation

Contact Info

Product

Resources

About