Multiomics Sequencing and AlphaFold2 Analysis of the Stereoselective Behavior of Mefentrifluconazole for Bioactivity Improvement and Risk Reduction.

As the first isopropanol chiral triazole fungicide, mefentrifluconazole has broad prospects for application. In this study, the stereoselective stability, bioactivity, fate, and biotoxicity were systematically investigated. Our results indicated that the stability of mefentrifluconazole enantiomers differed between environmental media, and they were stable in water and sediment in the dark. The bactericidal activity of R-mefentrifluconazole against the four target pathogens was 4.6-43 times higher than that of S-mefentrifluconazole. In the water-sediment system, S-mefentrifluconazole dissipated faster than R-mefentrifluconazole in water; however, its accumulation capacity was higher than that of R-mefentrifluconazole in sediment and zebrafish. S-Mefentrifluconazole induced more differentially expressed genes (DEGs) and differentially expressed proteins (DEPs) in zebrafish than did R-mefentrifluconazole. Multiomics sequencing results showed that S-mefentrifluconazole enhanced the antioxidant, detoxification, immune, and metabolic functions of zebrafish by interacting with related proteins. Based on AlphaFold2 modeling and molecular docking, mefentrifluconazole enantiomers had different binding modes with key target proteins in pathogens and zebrafish, which may be the main reason for the stereoselective differences in bioactivity and biotoxicity. Based on its excellent bioactivity and low biotoxicity, the R-enantiomer can be developed to improve the bioactivity and reduce the risk of mefentrifluconazole.

Growth, reproduction and biochemical toxicity of chlorantraniliprole in soil on earthworms (Eisenia fetida).

Diamide insecticides have become the fourth most commonly used insecticide class in the world. Chlorantraniliprole (CAP) is a first-generation diamide insecticide with broad application potential. In this experiment, the eco-toxicity of CAP in soil at 0.1, 1.0, 5.0 and 10.0mg/kg on earthworms (Eisenia fetida) was evaluated during a 42 d exposure. More specifically, the environmental fate and transport of CAP between soil and earthworms was monitored during the exposure period. The present results indicated that the CAP contents of 0.1, 1.0, 5.0 and 10.0mg/kg treatments decreased to no more than 20% in the soil after 42 d of exposure. The accumulation of CAP in earthworms was 0.03, 0.58, 4.28 and 7.21mg/kg earthworm (FW) at 0.1, 1.0, 5.0 and 10.0mg/kg after 42 d of exposure. At 0.1mg/kg and 1.0mg/kg, CAP had no effect on earthworms during the exposure period. The weight of earthworms was significantly reduced at 5.0 and 10.0mg/kg at 28 and 42 days after CAP application. After the 14th day, CAP induced excess production of reactive oxygen species (ROS) at 5.0 and 10.0mg/kg, resulting in oxidative damage to biomacromolecules. We believe that CAP has a high risk potential for earthworms when used at 5.0 and 10.0mg/kg.

Simultaneous determination of pyrifluquinazon and its main metabolite in fruits and vegetables by using QuEChERS-HPLC-MS/MS.

A rapid, reliable, and sensitive method is reported for the simultaneous analysis of pyrifluquinazon and its main metabolite NNI-0101-1H in fruits (strawberry and cherry) and vegetables (cucumber and tomato) using high-performance liquid chromatography coupled with tandem mass spectrometry. A modified, quick, easy, cheap, effective, rugged, and safe procedure was used for the sample pre-preparation. The target analytes were extracted with acetonitrile and then cleaned up using dispersive solid-phase extraction procedure with primary secondary amine. Sample analysis was performed using electrospray ionization in positive mode. Good linearities with the correlation coefficients higher than 0.9991 were obtained in the range of 1-1000 µg/L under the optimized conditions. The average recoveries of the pyrifluquinazon and NNI-0101-1H were in the range of 71.4-106.0% with the relative standard deviations 1.8-11.8% in all matrices at three spiked levels (10, 100, and 1000 µg/kg). The limit of quantification 10 µg/kg was set as the lowest spiked level. The developed method is reliable and effective for the routine monitoring of pyrifluquinazon and its metabolite NNI-0101-1H in fruits and vegetables to ensure food safety.

Residue analysis and risk assessment of tebuconazole in jujube (Ziziphus jujuba Mill).

In this study, a sensitive and reliable analytical method, based on a modified Quick, Easy, Cheap, Effective, Rugged and Safe procedure, was established for determination of tebuconazole in jujube. After extraction with acetonitrile, the samples were cleaned up by dispersive solid-phase extraction with primary secondary amine, and determined by high-performance liquid chromatography tandem mass spectrometry. At fortification levels of 0.01, 0.1 and 2.0 mg kg-1 , the average recoveries of tebuconazole in jujube were in the range 97.6-101.9%, with relative standard deviations of 1.5-3.5%. The dissipation and residual levels of tebuconazole in jujube under field conditions were investigated. Tebuconazole dissipated relatively slowly in jujube, with a half-life of 33.0 days. The terminal residue experiments of tebuconazole in jujube were conducted in four locations in China and the risk was evaluated using risk quotients (RQ). RQ values were found to be significantly lower than RQ = 1, indicating that the risk to human health of using the recommended doses of tebuconazole in jujube was not significant. This study could provide guidance for the safe and reasonable use of tebuconazole in jujube and serve as a reference for the establishment of limit of maximum residue in China.

Oxidative stress and gene expression of earthworm (Eisenia fetida) to clothianidin.

Neonicotinoid insecticides have become the most widely used pesticides in the world. Clothianidin is a novel neonicotinoid insecticide with a thiazolyl ring that exhibits excellent biological efficacy against a variety of pests. In the present study, the oxidative stress and genotoxicity of clothianidin on earthworms were evaluated. Moreover, the effective concentrations of clothianidin in artificial soil were monitored during the whole exposure period. The results showed that clothianidin was stable in artificial soil and that the residue concentrations were 0.094, 0.476, and 0.941mg/kg after 28 d of exposure, which represented changes no more than 10% compared to the concentrations on the 0th day. Additionally, both the concentration of and exposure time to clothianidin had a substantial influence on biomarkers in earthworms. At 0.5mg/kg and 1.0mg/kg, the reactive oxygen species (ROS) levels were greatly enhanced, causing changes in antioxidant enzyme activities, damage to biological macromolecules and abnormal expression of functional genes. Additionally, the present results showed that superoxide dismutase (SOD), DNA damage and heat shock protein 70 (HSP70) may be good indicators for environmental risk assessment of clothianidin to earthworms.

Gut pathobiome mediates behavioral and developmental disorders in biotoxin-exposed amphibians.

Emerging evidence suggests a link between alterations in the gut microbiome and adverse health outcomes in the hosts exposed to environmental pollutants. Yet, the causal relationships and underlying mechanisms remain largely undefined. Here we show that exposure to biotoxins can affect gut pathobiome assembly in amphibians, which in turn triggers the toxicity of exogenous pollutants. We used Xenopus laevis as a model in this study. Tadpoles exposed to tropolone demonstrated notable developmental impairments and increased locomotor activity, with a reduction in total length by 4.37%-22.48% and an increase in swimming speed by 49.96%-84.83%. Fusobacterium and Cetobacterium are predominant taxa in the gut pathobiome of tropolone-exposed tadpoles. The tropolone-induced developmental and behavioral disorders in the host were mediated by assembly of the gut pathobiome, leading to transcriptome reprogramming. This study not only advances our understanding of the intricate interactions between environmental pollutants, the gut pathobiome, and host health but also emphasizes the potential of the gut pathobiome in mediating the toxicological effects of environmental contaminants.

Dissipation rate and residual fate of thiamethoxam in tobacco leaves and soil exposed to field treatments.

A two-year field experiment was conducted in two different locations to investigate the dissipation rate and residual fate of thiamethoxam in tobacco leaves and soil by high performance liquid chromatography with UV detection. The average recoveries for green, cured tobacco leaves and soil ranged from 89.7 %-94.8 %, 90.6 %-94.4 % and 89.0%-92.8 %, respectively, with relative standard deviations between 2.7 % and 9.2 %. The dissipation rates of thiamethoxam were described by first-order kinetics and its half-life values were in the range of 3.9-4.4 days in green tobacco leaves and 12.0-19.1 days in soil, respectively. The residue levels of thiamethoxam at harvest time ranged from 0.020-0.541 mg/kg in cured tobacco leaves, and 0.005-0.019 mg/kg in soil, respectively.

The fate, acute, and subchronic risks of dinotefuran in the water-sediment system: A systematic analysis at the enantiomer level.

Environmental risks associated with neonicotinoid insecticides have attracted considerable attention. This study systematically investigated the stereoselective behavior of dinotefuran in a water-sediment system. The results showed that S-dinotefuran accumulated more easily in sediment and zebrafish. Although dinotefuran enantiomers and metabolites present a low risk to aquatic organisms, the risk of dinotefuran enantiomers to sediment organisms should be considered. Additionally, S-dinotefuran induced more remarkable oxidative damage in zebrafish than that of R-dinotefuran. Nevertheless, R-dinotefuran remarkably activated antioxidant and detoxifying enzymes. Multi-omics analyses revealed that S-dinotefuran induced more differentially expressed genes (DEGs) and differentially expressed proteins (DEPs) in zebrafish. In particular, S-dinotefuran inhibited the expression of ribosome- and proteasome-related genes and proteins, affecting the synthesis and degradation of proteins in zebrafish. R-dinotefuran remarkably activated peroxisome-related genes and proteins, thereby enhancing antioxidant and detoxification abilities of zebrafish. The stereoselective interactions between dinotefuran enantiomers and key DEPs were elucidated using AlphaFold2 modeling and molecular docking techniques, which may serve as the main reason for stereoselective subchronic toxicity. The present study is beneficial for the correct use of dinotefuran and provides an effective means for elucidating the mechanism of the stereoselective behavior of chiral compounds.

A systematic analysis of residue and risk of cyantraniliprole in the water-sediment system: Does metabolism reduce its environmental risk?

As a representative variety of diamide insecticides, cyantraniliprole has broad application prospects. In this study, the fate and risk of cyantraniliprole and its main metabolite J9Z38 in a water-sediment system were investigated. The present result showed that more J9Z38 was adsorbed in the sediment at the end of exposure. However, the bioaccumulation capacity of cyantraniliprole in zebrafish was higher than that of J9Z38. Cyantraniliprole had stronger influence on the antioxidant system and detoxification system of zebrafish than J9Z38. Moreover, cyantraniliprole induced more significant oxidative stress effect and more differentially expressed genes (DEGs) in zebrafish. Cyantraniliprole had significantly influence on the expression of RyR-receptor-related genes, which was confirmed by resolving their binding modes with key receptor proteins using AlphaFold2 and molecular docking techniques. In the sediment, both cyantraniliprole and J9Z38 had inhibitory effects on microbial community structure diversity and metabolic function, especially cyantraniliprole. The methane metabolism pathway, mediated by methanogens such as Methanolinea, Methanoregula, and Methanosaeta, may be the main pathway of degradation of cyantraniliprole and J9Z38 in sediments. The present results demonstrated that metabolism can reduce the environmental risk of cyantraniliprole in water-sediment system to a certain extent.

Earthworms synergize with indigenous soil functional microorganisms to accelerate the preferential degradation of the highly toxic S-enantiomer of the fungicide imazalil in soil.

The roles of soil and earthworm gut microorganisms in the degradation of the chiral fungicide imazalil (IMA) enantiomers were systemically studied in soil-earthworm systems. S-IMA degraded slower than R-IMA in soil without earthworms. After the addition of earthworms, S-IMA degraded faster than R-IMA. Methylibium was the potential degradative bacterium likely related to the preferential degradation of R-IMA in soil. However, the addition of earthworms significantly decreased the relative abundance of Methylibium, especially in R-IMA-treated soil. Meanwhile, a new potential degradative bacterium Aeromonas first appeared in soil-earthworm systems. Compared with enantiomer-treated soil, the relative abundance of indigenous soil bacterium Kaistobacter significantly boomed in enantiomer-treated soil with earthworms. Interestingly, Kaistobacter in the earthworm gut also obviously increased after exposure to enantiomers, particularly in S-IMA-treated soil, which was associated with the significant increase in Kaistobacter in soil. More importantly, the relative abundances of Aeromonas and Kaistobacter in S-IMA-treated soil were obviously higher than those in R-IMA-treated soil after the addition of earthworms. Moreover, these two potential degradative bacteria were also potential bacterial hosts of the biodegradation genes p450 and bph. Collectively, gut microorganisms are important helpers in soil pollution remediation by participating in the preferential degradation of S-IMA mediated by indigenous soil microorganisms.

Core bacteria carrying the genes associated with the degradation of atrazine in different soils.

Atrazine residues can pose serious threats to soil ecology and human health. Currently, the underlying relationship between soil microbial communities and the degradation genes associated with atrazine degradation remains unclear. In this study, the degradation characteristics of atrazine was investigated in ten different soil types. Further, diversity and abundance of degradation genes and succession of the bacterial community were also studied. The degradation of 10 mg/kg atrazine in different soil types exhibited an initial rapid trend followed by a gradual slowdown, adhering to the first-order kinetic equation. Atrazine significantly increased the absolute abundance of atz degradation genes. The increase in the absolute abundance of atzC gene was the largest, whereas that of atzA gene was the smallest, and the trzD gene was only detected in the Binzhou loam soil. Co-occurrence network analysis showed that the number of potential bacterial hosts of atzC was the highest compared with the other atz genes. Atrazine also altered the structural composition of the soil microbial community. The relative abundances of Ochrobactrum, Nocardiopsis, Lactobacillus, and Brevibacterium was increased in the atrazine-treated soils, while those of Conexibate, Solirubacter, and Micromonospora was decreased significantly compared with the control. Additionally, four atrazine-degrading bacterial strains Rhizobium AT1, Stenotrophomonas AT2, Brevibacterium AT3, and Bacillus AT4 were isolated from the atrazine-treated soils. After 14 d for inoculation, their degradation rate for 10 mg/L atrazine ranged from 17.56 % to 30.55 %. Moreover, the relative abundances of the bacterial genera, including these four isolates, in the atrazine-treated soil were significantly higher than those in the control, indicating that they were involved in the synergistic degradation of atrazine in the soil. This study revealed the degradation characteristics of atrazine, distribution of degradation genes, and succession of microbial communities, and explored the internal relationship between microbial community structure and atrazine degradation mechanisms in different soil types.

Response of soil bacterial community to repeated applications of carbendazim.

The effect of repeated carbendazim applications on functional diversity of culturable microorganisms and bacterial community composition was studied under field conditions. The functional diversity of soil culturable microbial community (Shannon index, H') reduced significantly (P<0.05) after the first introduction of carbendazim at levels of 0.94, 1.88 and 4.70 kg active ingredient (a.i.)ha(-1) and then recovered to that in the control with subsequent applications. An evident (P<0.01) difference in the bacterial community composition was observed after the second carbendazim application by Temperature Gradient Gel Electrophoresis (TGGE) analysis of 16S rRNA genes amplified from treated and control soils, which remained after the third and fourth treatments. Our results indicated that repeated carbendazim applications have a transient harmful effect on functional diversity of soil culturable microbial community and result in an alteration in bacterial community composition largely due to one species within the γ-proteobacterium.

Iprodione residues and dissipation rates in tobacco leaves and soil.

Field experiments were conducted in two different locations to determine the residue levels and dissipation rates of iprodione in tobacco leaves and soil. Iprodione 50% wettable powder formulation was sprayed once at 12.50 g/ha to study the dissipation behavior and three to four times at 8.33 g/ha (recommended dose) and 12.50 g/ha (1.5 times the recommended field dose) to determine the residue levels of iprodione in tobacco leaves and soil after repeated applications. Iprodione residues in both green tobacco leaves and soil dissipated to about 50% of the initial deposits after 7 days and then further dissipated to more than 90% after 35 days.The dissipation of iprodione followed first order kinetics and the calculated half-life values (T (1/2)) were 5.64-8.80 days in green tobacco leaves and 7.50-9.93 days in soil, respectively. Iprodione residue levels in flue-cured tobacco leaves 21 days after the third and fourth applications ranged from 7.61 to 40.98 mg/kg. Meanwhile, the residues detected in soil decreased to 0.010-0.117 mg/kg 21 days after the last treatment.

Dissipation and residues of myclobutanil in tobacco and soil under field conditions.

Field experiments were conducted in two different locations to determine the dissipation pattern and residue levels of myclobutanil in tobacco leaves and soil. Myclobutanil 12.5 % microemulsion (ME) formulation was sprayed once at 3.0 mL/ha, and the residues in green tobacco leaves dissipated to more than 50 % of the initial deposits 5 days after application and up to above 90 % after 21 days. The dissipation rate of myclobutanil in soil was lower than that in green tobacco leaves. The residues dissipated above 50 % of the initial deposits 7 days after treatment and dissipated about 90 % after 42 days. The calculated half-life values (T (1/2)) were found to be 4.89-6.77 days in green tobacco leaves and 12.88-19.20 days in soil, respectively. The ultimate residues of myclobutanil in flue-cured tobacco leaves and soil were determined after the third and fourth applications at levels of 2.0 and 3.0 mL/ha. Myclobutanil residues in cured tobacco leaves 21 days after the last treatment ranged from 0.85 to 3.27 mg/kg. Meanwhile, the residues detected in soil reached below 0.045 mg/kg 21 days after the last treatment.

Indigenous functional microbial degradation of the chiral fungicide mandipropamid in repeatedly treated soils: Preferential changes in the R-enantiomer.

This study investigated the indigenous functional microbial communities associated with the degradation of chiral fungicide mandipropamid enantiomers in soils repeatedly treated with a single enantiomer. The R-enantiomer degraded faster than the S-enantiomer, with degradation half-lives ranging from 10.2 d to 79.2 d for the R-enantiomer and 10.4 d to 130.5 d for the S-enantiomer. Six bacterial genera, (Burkholderia, Paraburkholderia, Hyphomicrobium, Methylobacterium, Caballeronia, and Ralstonia) with R-enantiomer substrate preference and three bacterial genera (Haliangium, Sorangium, and Sandaracinus) with S-enantiomer substate preference were responsible for the preferential degradation of the R-enantiomer and S-enantiomer, respectively. KEGG analysis indicated that Burkholderia, Paraburkholderia, Hyphomicrobium, and Methylobacterium were the dominant contributors to soil microbial metabolic functions. Notably, six microbial metabolic pathways and twelve functional enzyme genes were associated with the preferential degradation of the R-enantiomer, whose relative abundances in the R-enantiomer treatment were higher than those in the S-enantiomer treatment. A constructed biodegradation gene (BDG) protein database analysis further confirmed that Burkholderia, Paraburkholderia, Hyphomicrobium, Methylobacterium, and Ralstonia were the potential hosts of five dominant BDGs, bphA1, benA, bph, p450, and ppah. We concluded that bacterial genera Burkholderia, Paraburkholderia, Hyphomicrobium, and Methylobacterium may play pivotal roles in the preferential degradation of mandipropamid R-enantiomer in repeatedly treated soils.

Assessing the bioavailability and biotoxicity of spiromesifen and its main metabolite spiromesifen-enol (M01) reveals the defense mechanisms of earthworms (Eisenia fetida).

As a promising acaricide and potentially hazardous material, the defense mechanisms of non-target organisms to its exposure are unknown. This study investigates the bioavailability and biotoxicity of spiromesifen and spiromesifen-enol (M01), its main metabolite, in Eisenia fetida. The results showed that M01 was more persistent in the soil environment and E. fetida than spiromesifen. Transcriptome analysis indicated that the spiromesifen- and M01-induced differentially expressed genes (DEGs) were mainly enriched in lysosomal and phagosomal pathways. Analysis of the key common DEGs showed that both spiromesifen and M01 significantly influenced the lysosomes, phagosomes, antioxidant systems, and detoxification systems. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) showed that spiromesifen and M01 damaged E. fetida epidermis and enhanced lysosomal and phagosomal activities. Significant oxidative stress effects were observed at the end of exposure. The hydroxyl free radical (·OH-) content and neutral red retention time (NRRT) could serve as sensitive early biomarkers to predict their pollution. These results revealed the synergistic effects of the epidermis, lysosomes, phagosomes, antioxidant systems, and detoxification system in resisting spiromesifen- and M01-induced damage, which could contribute to the defense mechanisms of non-target organisms against these pollutants.

Indigenous functional microbial communities for the preferential degradation of chloroacetamide herbicide S-enantiomers in soil.

This study investigated indigenous functional microbial communities associated with the degradation of chloroacetamide herbicides acetochlor (ACE), S-metolachlor (S-MET) and their enantiomers in repeatedly treated soils. The results showed that biodegradation was the main process for the degradation of ACE, S-MET and their enantiomers. Eight dominant bacterial genera associated with the degradation were found: Amycolatopsis, Saccharomonospora, Mycoplasma, Myroides, Mycobacterium, Burkholderia, Afipia, and Kribbella. The S-enantiomers of ACE and S-MET were preferentially degraded, which mainly relied on Amycolatopsis, Saccharomonospora and Kribbella for the ACE S-enantiomer and Amycolatopsis and Saccharomonospora for the S-MET S-enantiomer. Importantly, the relative abundances of Amycolatopsis and Saccharomonospora increased by 146.3%-4467.2% in the S-enantiomer treatments of ACE and S-MET compared with the control, which were significantly higher than that in the corresponding R-enantiomer treatments (25.3%-4168.2%). Both metagenomic and qPCR analyses demonstrated that four genes, ppah, alkb, benA, and p450, were the dominant biodegradation genes (BDGs) potentially involved in the preferential degradation of the S-enantiomers of ACE and S-MET. Furthermore, network analysis suggested that Amycolatopsis, Saccharomonospora, Mycoplasma, Myroides, and Mycobacterium were the potential hosts of these four BDGs. Our findings indicated that Amycolatopsis and Saccharomonospora might play pivotal roles in the preferential degradation of the S-enantiomers of ACE and S-MET.

Systematic evaluation of chiral fungicide penflufen for the bioactivity improvement and input reduction using alphafold2 models and transcriptome sequencing.

Traditional risk assessment of pesticide concludes at the racemic level, which is often incomprehensive. In this study, systematic studies on environmental stability, bioactivity, and ecotoxicological effects of fungicide penflufen were carried out at the enantiomeric level. The single-enantiomer of penflufen was successfully separated and prepared, and their stability was verified in different environmental matrices. Meanwhile, bioactivity test indicated that S-(+)-penflufen had increased bioactivity with its bioactivities against Rhizoctonia solani, Fusarium oxysporum, and Fusarium moniliforme being factors of 7.8, 1.8, and 4.7, respectively greater than those of R-(-)-penflufen. Molecular docking results showed the strong hydrogen bond interactions with Leu300, enantiomer-specific hydrophobic interactions with Cys299, Arg91, and His93, and the greater binding energy between S-(+)-penflufen and succinate dehydrogenase of Rhizoctonia solani caused the selective bioactivity. Additionally, two enantiomers showed low acute toxicity whereas selective sub-chronic toxicity to earthworms. In sub-chronic toxicity test, the accumulated enantiomers caused abnormalities in intestinal tract structure, enzyme activities, and gene expression of earthworms, especially in the S-(+)-penflufen treatment. The selective interactions between penflufen enantiomers and key proteins were elucidated using molecular docking, which may be the main reason of stereoselective subchronic toxicity. S-(+)-penflufen has high bioactivity and low acute risk, it has great potential for development.

Enantioselective toxicity and oxidative stress effects of acetochlor on earthworms (Eisenia fetida) by mediating the signaling pathway.

Acetochlor (ACT) as a widely used chiral chloroacetamide herbicide is appropriate to evaluate the potential toxicity in soil ecosystems at enantiomeric level. The acute and subchronic toxicities of R-acetochlor (R-ACT) and S-acetochlor (S-ACT) on earthworms (Eisenia fetida) were investigated in the present study. Residual analyses showed that S-ACT degraded faster than R-ACT in artificial soil with half-lives of 16.5 and 21.7 d, respectively. Additionally, significant enantioselective acute toxicity in earthworms from between S-ACT and R-ACT (p < 0.05) was observed, and the acute toxicity of R-ACT were 1.9 and 1.5 times higher than those of S-ACT in the filter paper test and artificial soil test. The hydroxyl radical (OH-) content, superoxide dismutase (SOD) and antioxidant enzyme catalase (CAT) activities, and cytochrome P450 content in earthworms significantly increased under the influence of ACT enantiomers; however, the acetylcholinesterase (AchE) activity was significantly inhibited after exposure to the two enantiomers. Moreover, lipid peroxidation and DNA damage were induced by ACT enantiomers. The results of transcriptome sequencing indicated that R-ACT induced a stronger oxidative stress effect than S-ACT in earthworms by mediating signaling pathways, which may be the primary reason for the enantioselective toxicity between S-ACT and R-ACT. Overall, the results demonstrated that R-ACT has a higher risk than S-ACT in the soil environment, which is important for understanding the enantioselective behavior of chloroacetamide pesticides.

Enantioselective residues and toxicity effects of the chiral triazole fungicide hexaconazole in earthworms (Eisenia fetida).

The enantioselective toxic effect and environmental behavior of chiral pesticides have attracted increasing research attention. In this study, the enantioselective toxicity and residues of hexaconazole (HEX) in earthworms (Eisenia fetida) were investigated. In the present study, significant enantioselective degradation characteristics were observed in artificial soil with the R-enantiomer preferentially degrading (p < 0.05); however, no significant enantioselective bioaccumulation was observed in the earthworms (p > 0.05). The acute toxicity of S-(+)-HEX was higher than that of R-(-)-HEX in earthworms, with 48-h LC50 values of 8.62 and 22.35 µg/cm2, respectively. At 25 mg/kg, enantiospecific induction of oxidative stress was observed in earthworms; moreover, S-(+)-HEX had a greater influence on the contents of malonaldehyde, cytochrome P450, and 8-hydroxy-2-deoxyguanosine than R-(-)-HEX. These results were consistent with those of the enrichment analysis of differentially expressed genes. The transcriptome sequencing results showed that S-(+)-HEX had a more significant influence on steroid biosynthesis, arachidonic acid metabolism, and cell cycle processes than R-(-)-HEX, leading to abnormal biological function activities. These results indicate that S-(+)-HEX may pose a higher risk to soil organisms than R-(-)-HEX. This study suggests that the environmental risk of chiral pesticides to nontarget organisms should be assessed at the enantiomeric level.