cyhalothrin and 3-phenoxybenzoic-acid

There are few published data on the impact of combined exposure to multiple pesticides (coexposure) on levels of biomarkers of exposure in workers, which may alter their toxicokinetics and thus the interpretation of biomonitoring data. This study aimed to assess the impact of coexposure to two pesticides with shared metabolism pathways on levels of biomarkers of exposure to pyrethroid pesticides in agricultural workers. The pyrethroid lambda-cyhalothrin (LCT) and the fungicide captan were used as sentinel pesticides, since they are widely sprayed concomitantly in agricultural crops. Eighty-seven (87) workers assigned to different tasks (application, weeding, picking) were recruited. The recruited workers provided two-consecutive 24-h urine collections following an episode of lambda-cyhalothrin application alone or in combination with captan or following tasks in the treated fields, as well as a control collection. Concentrations of lambda-cyhalothrin metabolites - 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-cyclopropanecarboxylic acid (CFMP) and 3-phenoxybenzoic acid (3-PBA) - were measured in the samples. Potential determinants of exposure established in a previous study, including the task performed and personal factors were documented by questionnaire. Multivariate analyses showed that coexposure did not have a statistically significant effect on the observed urinary levels of 3-PBA (Exp(β) (95% confidence interval (95% CI)): 0.94 (0.78-1.13)) and CFMP (1.10 (0.93-1.30). The repeated biological measurements ("time variable") - defined as the within-subjects variable - was a significant predictor of observed biological levels of 3-PBA and CFMP; the within-subjects variance (Exp(β) (95% (95% CI)) for 3-PBA and CFMP was 1.11 (1.09-3.49) and 1.25 (1.20-1.31). Only the main occupational task was associated with urinary levels of 3-PBA and CFMP. Compared to the weeding or picking task, the pesticide application task was associated with higher urinary 3-PBA and CFMP concentrations. In sum, coexposure to agricultural pesticides in the strawberry fields did not increase pyrethroid biomarker concentrations at the exposure levels observed in the studied workers. The study also confirmed previous data suggesting that applicators were more exposed than workers assigned to field tasks such as weeding and picking.

Topics: Biomarkers; Captan; Environmental Monitoring; Farmers; Humans; Insecticides; Pesticides; Pyrethrins

Pyrethroids are synthetic insecticides commonly used in agriculture and homes due to their low toxicity to mammals and effectiveness at low doses. However, exposure to pyrethroids can cause various symptoms, depending on the route of exposure. To measure human exposure to pyrethroids, researchers used wastewater-based epidemiology (WBE) with polar organic chemical integrative samplers (POCIS) sampling. This approach is a cost-effective and efficient way to assess exposure to pyrethroids. The study aimed to evaluate the exposure of an urban population in Brazil to pyrethroids during the COVID-19 pandemic using WBE with POCIS sampling. Researchers analyzed 3-phenoxybenzoic acid (3-PBA) in wastewater using passive sampling with POCIS, which was extracted with methanol and analyzed using UPLC-MS/MS. The range of CTWA concentrations of 3-PBA in wastewater was 24.3-298.2 ng L

Topics: Brazil; Chromatography, Liquid; COVID-19; Humans; Insecticides; Pandemics; Pyrethrins; Risk Assessment; Tandem Mass Spectrometry; Urban Population; Wastewater; Wastewater-Based Epidemiological Monitoring

Pesticide residues in food are a critical issue affecting food safety. The pesticide contaminants in food include currently used, legacy pesticides, and degradation products. Thus, this study analyzed the effects of planting and processing on the transfer and degradation of pesticide residues in corn. Specifically, we studied the transportation and transformation of 26 organochlorine pesticides (OCPs), 6 currently used pesticides, and 2 degradation products throughout corn planting and flour processing. For the currently used pesticide, diquat applied in this study did not significantly affect its concentration in soils. Different from this, λ-cyhalothrin application increased its concentration in soils. Therein, λ-cyhalothrin degraded to 3-PBA in a short time, and 3-PBA degraded faster than λ-cyhalothrin. The concentrations of legacy, currently used pesticides, and degradation products were higher in bran than in corn flour, indicating that the outer portions of corn kernels accumulated more pesticides. However, the results for λ-cyhalothrin were the opposite, indicating that the surrounding of bran is more favorable for degrading λ-cyhalothrin. The short- and long-term risks of consumer exposure to these pesticide residues via corn consumption are relatively insignificant based on the implementation time and dose in this study.

Topics: Flour; Pesticide Residues; Pesticides; Soil; Zea mays

This study aimed at gaining more insights into the impact of pesticide coexposure on the toxicokinetics of biomarkers of exposure. This was done by conducting an in vivo experimental case-study with binary mixtures of lambda-cyhalothrin (LCT) and captan and by assessing its impact on the kinetic profiles of LCT biomarkers of exposure. Groups of male Sprague-Dawley rats were exposed orally by gavage to LCT alone (2.5 or 12.5 mg/kg bw) or to a binary mixture of LCT and captan (2.5/2.5 or 2.5/12.5 or 12.5/12.5 mg/kg bw). In order to establish the temporal profiles of the main metabolites of LCT, serial blood samples were taken, and excreta (urine and feces) were collected at predetermined intervals up to 48 h post-dosing. Major LCT metabolites were quantified in these matrices: 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-cyclopropane carboxylic (CFMP), 3-phenoxybenzoic acid (3-PBA), 4-hydroxy-3-phenoxybenzoic acid (4-OH3PBA). There was no clear effect of coexposure at the low LCT dose on the kinetics of CFMP and 3-PBA metabolites, based on the combined assessment of temporal profiles of these metabolites in plasma, urine and feces; however, plasma levels of 3-PBA were diminished in the coexposed high-dose groups. A significant effect of coexposure on the urinary excretion of 4-OH3PBA was also observed while fecal excretion was not affected. The temporal profiles of metabolites in plasma and in excreta were further influenced by the LCT dose. In addition, the study revealed kinetic differences between metabolites with a faster elimination of 3-PBA and 4-OH3BPA compared to CFMP. These results suggest that the pyrethroid metabolites CFMP and 3-PBA, mostly measured in biomonitoring studies, remain useful as biomarkers of exposure in mixtures, when pesticide exposure levels are below the reference values. However, the trend of coexposure effect observed in the benzyl metabolite pathway (in particular 4-OH3BPA) prompts further investigation.

Topics: Animals; Benzoates; Biomarkers; Captan; Insecticides; Male; Nitriles; Pesticides; Pyrethrins; Rats; Rats, Sprague-Dawley; Toxicokinetics

In the present study, the endocrine toxicity of LCT and PBA was investigated through exposure to Eremias argus for two weeks under environmental relevant concentration. RNA-sequencing identified 4442 and 4653 differentially expressed genes in lizard liver after LCT and PBA exposure. Four differentially expressed genes (hsd17β, ar, sult, ugt) related with hypothalamic-pituitary-gonadal axis were quantified by qPCR. The expression of genes associated with HPG axis in different tissues differed significantly. In LCT treatment group, ar, cyp17 and hsd3β genes involved in testosterone synthesis and transportation were significantly decreased in lizard testes, and the spermatogensis was inhibited in the testes, which indicated the anti-androgenic activity of LCT. After PBA exposure, the genes related with estradiol synthesis, transportation and metabolism, such as hsd17β, erα, ugt in lizard liver were important biomarkers and the significant decrease of estradiol level was highly correlated with hsd17β, erα, ugt gene expressions. The relative high binding affinity of PBA with ERα further demonstrated the anti-estrogenic activity of PBA. Our results elucidate the different toxic mechanism of LCT and PBA on lizard endocrine system at environmental relevant concentration. Pyrethroids metabolism may cause more seriously toxicity rather than detoxification.

Topics: Animals; Benzoates; Lizards; Male; Nitriles; Pyrethrins

The disturbance of the thyroid system and elimination of chiral pyrethroid pesticides with respect to enantioselectivity in reptiles have so far received limited attention by research. In this study, bioaccumulation, thyroid gland lesions, thyroid hormone levels, and hypothalamus-pituitary-thyroid axis-related gene expression in male Eremias argus were investigated after three weeks oral administration of lambda-cyhalothrin (LCT) enantiomers. In the lizard liver, the concentration of LCT was negatively correlated with the metabolite-3-phenoxybenzoic acid (PBA) level during 21 days of exposure. (+)-LCT exposure induced a higher thyroid follicular epithelium height than (-)-LCT exposure. The thyroxine levels were increased in both treated groups while only (+)-LCT exposure induced a significant change in the triiodothyronine (T3) level. In addition, the expressions of hypothalamus-pituitary-thyroid axis-related genes including thyroid hormone receptors (trs), deiodinases (dios), uridinediphosphate glucuronosyltransferase (udp), and sulfotransferase (sult) were up-regulated after exposure to the two enantiomers. (+)-LCT treatment resulted in higher expression of trs and (-)-LCT exposure led to greater stimulation of dios in the liver, which indicated PBA-induced antagonism on thyroid hormone receptors and LCT-induced disruption of thyroxine (T4) deiodination. The results suggest the (-)-LCT exposure causes higher residual level in lizard liver while induces less disruption on lizard thyroid activity than (+)-LCT.

Topics: Animals; Benzoates; Endocrine Disruptors; Iodide Peroxidase; Liver; Lizards; Male; Nitriles; Pesticides; Pyrethrins; Receptors, Thyroid Hormone; Stereoisomerism; Thyroid Gland; Thyroid Hormones; Thyroxine

3-Phenoxybenzoic acid (3-PBA) is a common metabolite of several pyrethroid pesticides of differing potency and also occurs as a residue in foods resulting from environmental degradation of parent pyrethroid compounds. Thus, 3-PBA in urine is not a specific biomarker of exposure to a particular pyrethroid. However, an approach derived from the use of Biomonitoring Equivalents (BEs) can be used to estimate a conservative initial screening value for a tiered assessment of population data on 3-PBA in urine. A conservative generic urinary excretion fraction for 3-PBA was estimated from data for five pyrethroid compounds with human data. Estimated steady-state urinary 3-PBA concentrations associated with reference doses and acceptable daily intakes for each of the nine compounds ranged from 1.7 μg/L for cyhalothrin and deltamethrin to 520 μg/L for permethrin. The lower value can be used as a highly conservative Tier 1 screening value for assessment of population urinary 3-PBA data. A second tier screening value of 87 μg/L was derived based on weighting by relative exposure estimates for the different pyrethroid compounds, to be applied as part of the data evaluation process if biomonitoring data exceed the Tier 1 value. These BE values are most appropriately used to evaluate the central tendency of population biomarker concentration data in a risk assessment context. The provisional BEs were compared to available national biomonitoring data from the US and Canada.

Topics: Benzoates; Biomarkers; Environmental Exposure; Environmental Monitoring; Environmental Pollutants; Humans; Insecticides; Nitriles; Pesticides; Pyrethrins; Risk Assessment

The contamination of agricultural lands by pesticides is a serious environmental issue. Consequently, the development of bioremediation methods for different active ingredients, such as pyrethroids, is essential. In this study, the enantioselective biodegradation of (±)-lambda-cyhalothrin ((±)-LC) by marine-derived fungi was studied. Experiments were performed with different fungi strains (Aspergillus sp. CBMAI 1829, Acremonium sp. CBMAI 1676, Microsphaeropsis sp. CBMAI 1675 and Westerdykella sp. CBMAI 1679) in 3% malt liquid medium with 100 mg L

Topics: Aspergillus; Benzoates; Biodegradation, Environmental; Fungi; Insecticides; Nitriles; Pesticides; Pyrethrins; Seawater

Lambda-cyhalothrin (LTC) [α-cyano-3-phenoxybenzyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclo-propanecarboxylate] is a synthetic type II pyrethroid insecticide commonly used in residential and agricultural areas. The potential hepatotoxicity of pyrethroids remains unclear and could easily be assessed by measuring common clinical indicators of liver disease. To understand more about the potential risks for humans associated with LTC exposure, male adult rats were orally exposed to 6.2 and 31.1 mg/kg bw of LTC for 7, 30, 45, and 60 days. Histopathological changes and alterations of main parameters related to oxidative stress and inflammatory responses in the liver were evaluated. Further, lambda-cyhalothrin metabolites [3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-cyclopropane carboxylic acid (CFMP), 4-hydroxyphenoxybenzoic acid (4-OH-3-PBA), and 3-phenoxybenzoic acid (3-PBA)] in the liver tissues were identified and quantified by ultra-high-performance liquid chromatography coupled to quadripole time-of-flight mass spectrometry (UHPLC-MS-Q-ToF). Results revealed that LTC exposure significantly increased markers of hepatic oxidative stress in a time-dependent and dose-dependent manner, and this was associated with an accumulation of CFMP and 3-PBA in the liver tissues. In addition, the levels of tumor necrosis factor-α (TNF-α) and interleukin (IL-6 and IL-1β) gene expressions were significantly increased in the liver of exposed rats compared to controls. Correlation analyses revealed that CFMP and 3-PBA metabolite levels in the liver tissues were significantly correlated with the indexes of oxidative stress, redox status, and inflammatory markers in rats exposed to lambda-cyhalothin. Overall, this study provided novel evidence that hepatic damage is likely due to increased oxidative stress and inflammation under the condition of acute and subchronic exposure to lambda-cyhalothrin and that LTC metabolites (CFMP and 3-PBA) could be used as potential biomarker in human biomonitoring studies.

Topics: Animals; Benzoates; Chemical and Drug Induced Liver Injury; Environmental Monitoring; Gene Expression; Insecticides; Liver Diseases; Male; Nitriles; Oxidative Stress; Pyrethrins; Rats; Tumor Necrosis Factor-alpha

In this study, the bioavailability and enantioselectivity differences between bifenthrin (BF, typeⅠpyrethroid) and lambad-cyhalothrin (LCT, type Ⅱ pyrethroid) in earthworm (Eisenia fetida) were investigated. The bio-soil accumulation factors (BSAFs) of BF was about 4 times greater than that of LCT. LCT was degraded faster than BF in soil while eliminated lower in earthworm samples. Compound sorption plays an important role on bioavailability in earthworm, and the soil-adsorption coefficient (K(oc)) of BF and LCT were 22 442 and 42 578, respectively. Metabolic capacity of earthworm to LCT was further studied as no significant difference in the accumulation of LCT between the high and low dose experiment was found. 3-phenoxybenzoic acid (PBCOOH), a metabolite of LCT produced by earthworm was detected in soil. The concentration of PBCOOH at high dose exposure was about 4.7 times greater than that of in low dose level at the fifth day. The bioaccumulation of BF and LCT were both enantioselective in earthworm. The enantiomer factors of BF and LCT in earthworm were approximately 0.12 and 0.65, respectively. The more toxic enantiomers ((+)-BF and (-)-LCT) had a preferential degradation in earthworm and leaded to less toxicity on earthworm for racemate exposure. In combination with other studies, a liner relationship between Log BSAF(S) and Log K(ow) was observed, and the Log BSAF(S) decreased with the increase of Log K(ow).

Topics: Animals; Benzoates; Biological Availability; Environmental Monitoring; Nitriles; Oligochaeta; Pesticides; Pyrethrins; Soil; Soil Pollutants; Stereoisomerism

Lambda-cyhalothrin (LCT) is a widely used pyrethroid with neurotoxicity. However, little is known about the toxicokinetics of LCT in reptiles. In this study, the absorption, distribution, metabolism and excretion of LCT in Chinese lizards (Eremias Argus) were determined following a single dose (10 mg kg

Topics: Adipose Tissue; Administration, Oral; Animals; Benzoates; Birds; Brain; Chemical and Drug Induced Liver Injury; Half-Life; Insecticides; Liver; Lizards; Male; Nitriles; Pyrethrins; Skin; Stereoisomerism; Tissue Distribution

Cyhalothrin is a common environmental pollutant which poses increased risks to non-target organisms including human beings. This study reported for the first time a newly isolated strain, Bacillus thuringiensis ZS-19 completely degraded cyhalothrin in minimal medium within 72 h. The bacterium transformed cyhalothrin by cleavage of both the ester linkage and diaryl bond to yield six intermediate products. Moreover, a novel degradation pathway of cyhalothrin in strain ZS-19 was proposed on the basis of the identified metabolites. In addition to degradation of cyhalothrin, this strain was found to be capable of degrading 3-phenoxybenzoic acid, a common metabolite of pyrethroids. Furthermore, strain ZS-19 participated in efficient degradation of a wide range of pyrethroids including cyhalothrin, fenpropathrinn, deltamethrin, beta-cypermethrin, cyfluthrin and bifenthrin. Taken together, our results provide insights into the mechanism of cyhalothrin degradation and also highlight the promising potentials of B.thuringiensis ZS-19 in bioremediation of pyrethroid-contaminated environment. This is the first report of (i) degradation of cyhalothrin and other pyrethroids by B.thuringiensis, (ii) identification of 3-phenoxyphenyl acetonitrile and N-(2-isoproxy-phenyl)-4-phenoxy-benzamide as the metabolites in the degradation pathway of pyrethroids, and (iii) a pathway of degradation of cyhalothrin by cleavage of both the ester linkage and diaryl bond in a microorganism.

Topics: Bacillus thuringiensis; Benzoates; Biodegradation, Environmental; Fungicides, Industrial; Kinetics; Metabolic Networks and Pathways; Metabolome; Metabolomics; Nitriles; Phylogeny; Pyrethrins; RNA, Ribosomal, 16S

Pseudomonas aeruginosa strain GF31, isolated from a contaminated soil, can effectively degrade β-cypermethrin (β-CP), as well as fenpropathrin, fenvalerate, and cyhalothrin. The highest level of degradation (81.2 %) was achieved with the addition of peptone. Surprisingly, the enzyme responsible for degradation was mainly localized to the extracellular areas of the bacteria, in contrast to the other known pyrethroid-degrading enzymes, which are intracellular. Although intact bacterial cells function at about 30 °C for biodegradation, similar to other degrading strains, the crude extracellular extract of strain GF31 remained biologically active at 60 °C. Moreover, the extract fraction showed good storage stability, maintaining >50 % of its initial activity following storage at 25 °C for at least 20 days. Significant differences in the characteristics of the crude GF31 extracellular extract compared with the known pyrethroid-degrading enzymes indicate the presence of a novel pyrethroid-degrading enzyme. Furthermore, the identification of 3-phenoxybenzoic acid and 2,2-dimethylcyclopropanecarboxylate from the degradation products suggests the possibility that β-CP degradation by both the strain and the crude extracellular fraction is achieved through a hydrolysis pathway. Further degradation of these two metabolites may lead to the development of an efficient method for the mineralization of these types of pollutants.

Topics: Bacterial Proteins; Benzoates; Biodegradation, Environmental; Carboxy-Lyases; Environmental Pollutants; Insecticides; Nitriles; Oxidoreductases; Phylogeny; Pseudomonas aeruginosa; Pyrethrins; RNA, Bacterial; RNA, Ribosomal, 16S

A bacterial strain ZS-S-01, newly isolated from activated sludge, could effectively degrade fenvalerate and its hydrolysis product 3-phenoxybenzoic acid (3-PBA). Based on the morphology, physiological biochemical characteristics, and 16 S rDNA sequence, strain ZS-S-01 was identified as Stenotrophomonas sp. Strain ZS-S-01 could also degrade and utilize deltamethrin, beta-cypermethrin, beta-cyfluthrin, and cyhalothrin as substrates for growth. Strain ZS-S-01 was capable of degrading fenvalerate rapidly without a lag phase over a wide range of pH and temperature, even in the presence of other carbon sources, and metabolized it to yield 3-PBA, then completely degraded it. No persistent accumulative product was detected by HPLC and GC/MS analysis. Studies on biodegradation in various soils showed that strain ZS-S-01 demonstrated efficient degradation of fenvalerate and 3-PBA (both 50 mg·kg(-1)) with a rate constant of 0.1418-0.3073 d(-1), and half-lives ranged from 2.3 to 4.9 days. Compared with the controls, the half-lives for fenvalerate and 3-PBA reduced by 16.9-156.3 days. These results highlight strain ZS-S-01 may have potential for use in bioremediation of pyrethroid-contaminated environment.

Topics: Benzoates; Biodegradation, Environmental; DNA, Bacterial; Nitriles; Pyrethrins; RNA, Ribosomal, 16S; Sequence Analysis, DNA; Sewage; Soil Pollutants; Stenotrophomonas

A preliminary evaluation was undertaken on the safety aspects in mosquito net impregnation with lambdacyhalothrin, on the operators and users of the treated nets. The detection by HPLC of one of the principal metabolites of lambdacyhalothrin, 3-phenoxy benzoic acid (3-PBA) in blood samples of the users and operators in very small quantities (0.01 to 0.02 ng/microliters) showed that absorption of the insecticide was minimum. Clinical examination and analysis of different biochemical parameters in blood and serum samples showed in spite of the minimal absorption of the insecticide, there was no immediate adverse effect.

Topics: Animals; Bedding and Linens; Benzoates; Humans; Insecticides; Mosquito Control; Nitriles; Occupational Diseases; Pyrethrins