Enantiomeric analysis of pyrethroids and organophosphorus insecticides

Jiménez-Jiménez, Sara; Casado, Natalia; García, María Ángeles; Marina, Marı́a Luisa

doi:10.1016/j.chroma.2019.06.066

Cited by 23 publications

(6 citation statements)

References 73 publications

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“…40,62 Pyrethroids usually have several chiral centers, often at the cyclopropane ring, creating multiple stereoisomers with variable degrees of toxicity. 64,65 The efficacy of the organophosphorus pesticide stereoisomers depends on their structure, with phosphorus chirality making a greater impact on the variation in activity than carbon chirality. [66][67][68] The difference between stereoisomer activities ranges from a factor of 1.5-20.0 or more, 69 but a 22-fold difference was observed between the (R) and (S) forms of malaoxon, an oxidation product of malathion, in their inhibitory potential for acetylcholinesterase from bovine (Artiodactyla: Bovidae) erythrocytes.…”

Section: Discussionmentioning

confidence: 99%

Toxicity and repellent activity of monoterpene enantiomers to rice weevils (Sitophilus oryzae)

Fouad

Tavares²,

Zanuncio

2021

Pest Management Science

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BACKGROUND: The rice weevil, Sitophilus oryzae (L., 1763) (Coleoptera: Curculionidae), is a stored grain/seed pest of several crops. Botanicals represent an option to manage this pest, especially those with high toxicity determined by its structure and physicochemical properties and low residue left behind on treated grains/seeds. Enantiomers are bioactive molecules in organic processes. The aim of this study was to evaluate the insecticidal activity of two enantiomeric forms of the monoterpenes citronellal, limonene, linalool, menthone and ⊍-pinene against S. oryzae adults through contact, fumigant and repellent assays.RESULTS: All results were compared with absolute acetone as the negative control and those from contact assays also with malathion as the positive control. (S)-(−)-linalool was the most toxic by contact to S. oryzae and (S)-(−)-menthone through fumigation, while the two enantiomeric forms of menthone and ⊍-pinene were the best repellents. CONCLUSIONS: The high toxicity of only one of the two monoterpene enantiomers showed the importance of form and percentage of enantiomer in the commercial product, which affect the success of the product to controlling S. oryzae.

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Section: Discussionmentioning

confidence: 99%

Toxicity and repellent activity of monoterpene enantiomers to rice weevils (Sitophilus oryzae)

Fouad

Tavares²,

Zanuncio

2021

Pest Management Science

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“…Some studies have also measured not only pyrethroid compounds but also their enantiomers. Enantiomers have the same chemical formula but can exhibit different biological activities, including estrogenicity [ 56 ]. Among these is the evaluation of the enantiomers of bifenthrin, which is another pyrethroid compound.…”

Section: Iata For Estrogenicitymentioning

confidence: 99%

Integrated Assessment for the Estrogenic Effects of Pyrethroid Compounds: Defining the Molecular Initiating Events and Key Events for the Adverse Outcome Pathway

Ortiz,

Park,

Lee

et al. 2024

Toxics

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Pyrethroids, which are derived from natural insecticides found in chrysanthemum flowers, are widely utilized in various sectors, including agriculture, forestry, horticulture, and personal insect protection. Due to their widespread use, concerns have arisen regarding their potential estrogenic effects on female reproductive health. This review aims to address data gaps and inconsistencies in previous studies by defining molecular initiating events and key events within the adverse outcome pathway associated with pyrethroid-induced estrogenic effects. To achieve this, we propose utilizing Integrated Approaches to Testing and Assessment (IATA), which incorporate in vitro assays and in vivo assessments to comprehensively investigate the estrogenic effects of pyrethroids. An initial search was conducted in the PubMed database to identify relevant articles. Subsequently, the findings were classified according to the IATA strategy. This review provides an overview of the current understanding of pyrethroids and their estrogenic effects, identifies data gaps, and highlights the use of IATA in existing studies on the estrogenic effects of various pyrethroids. It emphasizes the urgent need for comprehensive research on the estrogenic effects of pyrethroids and highlights the importance of standardized testing methods like IATA to accurately assess their impact on human and environmental health. By promoting the use of Integrated Testing Strategies (ITSs) and addressing data gaps, researchers and regulators can enhance the accuracy of assessments, ensuring better protection of human and environmental health from the potential estrogenic effects of pyrethroid exposure.

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“…They can be classified according to different aspects such as their use, toxicity, chemical structure, or media lifetime. Based on their chemical structures, it is possible to differentiate organophosphorus pesticides, carbamates, pyrethroids, organochlorines, triazines, benzimidazoles, and nitro compounds [12,13]. Among the recent food alerts reported for the occurrence of pesticides in foods, a huge number have been related to the occurrence of organophosphorus pesticides, such as chlorpyrifos and dimethoate (Figure 2a).…”

Section: Pesticidesmentioning

confidence: 99%

What Are We Eating? Surveying the Presence of Toxic Molecules in the Food Supply Chain Using Chromatographic Approaches

Casado,

Berenguer,

Câmara

et al. 2024

Molecules

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Consumers in developed and Western European countries are becoming more aware of the impact of food on their health, and they demand clear, transparent, and reliable information from the food industry about the products they consume. They recognise that food safety risks are often due to the unexpected presence of contaminants throughout the food supply chain. Among these, mycotoxins produced by food-infecting fungi, endogenous toxins from certain plants and organisms, pesticides, and other drugs used excessively during farming and food production, which lead to their contamination and accumulation in foodstuffs, are the main causes of concern. In this context, the goals of this review are to provide a comprehensive overview of the presence of toxic molecules reported in foodstuffs since 2020 through the Rapid Alert System for Food and Feed (RASFF) portal and use chromatography to address this challenge. Overall, natural toxins, environmental pollutants, and food-processing contaminants are the most frequently reported toxic molecules, and liquid chromatography and gas chromatography are the most reliable approaches for their control. However, faster, simpler, and more powerful analytical procedures are necessary to cope with the growing pressures on the food chain supply.

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Enantiomeric analysis of pyrethroids and organophosphorus insecticides

Cited by 23 publications

References 73 publications

Toxicity and repellent activity of monoterpene enantiomers to rice weevils (Sitophilus oryzae)

Toxicity and repellent activity of monoterpene enantiomers to rice weevils (Sitophilus oryzae)

Integrated Assessment for the Estrogenic Effects of Pyrethroid Compounds: Defining the Molecular Initiating Events and Key Events for the Adverse Outcome Pathway

What Are We Eating? Surveying the Presence of Toxic Molecules in the Food Supply Chain Using Chromatographic Approaches

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