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Neonicotinoids can control crop pests with high efficiency and low cost and have quickly swept one-fourth of the global insecticide market since the launch of imidacloprid in 1991. Imidacloprid and acetamiprid, the first generation of neonicotinoids, and dinotefuran, the representative of third generation of neonicotinoids, were applied on tomato plants individually to investigate neonicotinoid effects on tomato fruit quality, especially on appearance parameters, sugar, acid, and aroma compounds. Compared with the control, fewer differences in the transcriptome profile, sugar, acid, and volatile organic compound (VOC) contents, and sensory analysis results were shown in dinotefuran treatments than in the other two treatments. Therefore, dinotefuran was more recommended to control pests of tomatoes with less loss of fruit flavor and quality as well as lower ecological risks.

This study explored the repair effect of Selenium nanoparticles (Se-NPs) on tomato under the stress of Penthiopyrad (Pen), and expected to select out the optimal concentration and the application time of Se-NPs, to maximize the repair effect without causing phytotoxicity. The results showed that Pen induced severe oxidative stress on tomato and inhibited the growth and flavor quality of fruit. Compared with the control, the application of 1 mg/L Se-NPs at the immature green stage significantly improved the antioxidant capacity of tomato to reduce the MDA content. Besides, the plant hormones were synthesized normally, the contents of soluble sugars, volatile compounds and nutrients were increased, and the contents of organic acids were decreased in the 1 mg/L Se-NPs + Pen treatment group, which finally repaired the fruit flavor and quality. Therefore, the application of 1 mg/L Se-NPs and at the immature green stage represented a promising strategy for repairing the inhibitory effect of Pen on tomato fruit growth and flavor quality.

In this study, the enantioselective activity of the chiral fungicide triticonazole (TRZ) against target pathogens of seed-borne diseases and the effect on the early phenotypic indexes and physiological and biochemical indexes of wheat following the soaking of seeds were studied. S-TRZ had low fungicidal activity and significantly inhibited the germination of wheat seeds. Seedlings in the S-TRZ treatment group suffered severe oxidative damage; the contents of glutathione (GSH) and malondialdehyde (MDA) were significantly increased. S-TRZ significantly inhibited the synthesis of gibberellin (GA) and ethylene (ETH), while it significantly increased that of jasmonic acid (JA). R-TRZ showed the highest activity against two smut fungi; the treatment of seeds with 5 g (ai)/100 kg R-TRZ had little influence on early wheat growth. The plant hormones were synthesized normally; seedlings grew well, and the fresh weight increased significantly following this treatment. Based on these data, we propose to develop and apply R-TRZ using the national recommended doses to control seed-borne diseases of wheat.

This study investigated the enantioselective effects of S-, R-, and rac-penthiopyrad (PEN) on the flavor quality of tomato fruit through the levels of sugars, acids, volatiles, and nutrients and explored the potential mechanism by combined analysis of the transcriptome and metabolome. The results revealed that the S-enantiomer increased the content of soluble sugars while decreasing the content of organic acids, thereby increasing the taste of tomato fruit. Furthermore, S-(+)-PEN promoted the accumulation of volatile compounds and nutrients (total phenols, flavonoids, and vitamin C). Transcriptome and metabolome data showed that the S-enantiomer improved fruit flavor and quality by influencing metabolites and genes in glycolysis, starch and sucrose metabolism, the citrate cycle, and amino acid biosynthesis pathways. However, R-(-)-PEN had a negative effect on tomato flavor. The effect of the racemate on fruit flavor quality was between a pair of enantiomers. The comprehensive data of PEN enantiomers will provide theoretical support for the application of PEN in tomatoes. Thus, developing enantiopure S-(+)-PEN products might be more conducive to the flavor and quality of the tomato fruit.

Difenoconazole is widely used in crop growth, however, its effects on the quality of agricultural products are poorly studied. In this study, the application of difenoconazole on tomato plants could increase soluble sugar content, reduce organic acid and raise accumulation of nutrient-related metabolites during late fruit ripening. Consumer surveys in our study showed that the treatment of difenoconazole tomatoes group had higher sweetness and lower acidity, and those tomatoes were preferred by consumers. Alterations in fruit flavor-related attributes were at least in part corroborated by the abundance of transcripts related to sucrose (SlLin5, SlLin7, SlSuS2, SlSuS6, SlSPS1, SlSPS3) and organic acids (CS, ICDH, cMDH) anabolism. Furthermore, the difenoconazole also significantly promoted the expression of phytohormones synthesis genes, and consequently increased abscisic acid and ethylene levels. Our study not only provides theoretical support for the use of difenoconazole on tomatoes at the level of flavor quality and nutritional health, but also provides valuable information on the mechanism of triazole fungicides in the flavor quality of tomato fruits.

Background: The most commonly used organochlorine pesticide nowadays, chlorothalonil (CHI), is ubiquitous in a natural environment and poses many adverse effects to organisms. Unfortunately, the toxicity mechanisms of CHI have not been clarified yet.Results: This study found that the CHI based on acceptable daily intake (ADI) level could induce metabolic syndrome (MetS) in mice, including obesity, hepatic steatosis, dyslipidemia, and insulin resistance. In addition, exposure to reglementary-dose CHI could induce an imbalance in the gut microbiota of mice, resulting in a significant increase in the ratio of Firmicutes to Bacteroidetes. Furthermore, the results of the antibiotic treatment and gut microbiota transplantation experiments showed that the reglementary-dose CHI could induce MetS in mice in a gut microbiota-dependent manner. Based on the results of targeted metabolomics and gene expression analysis, the reglementary-dose CHI could disturb the serum metabolism of bile acids (BAs) in mice, causing the inhibition of the signal response of BAs receptor farnesol X receptor (FXR) and leading to glycolipid metabolism disorders in liver tissue and epididymal white adipose tissue (epiWAT) of mice. The administration of FXR agonist GW4064 and CDCA could significantly improve the reglementary-dose CHI-induced MetS in mice.Conclusions: In conclusion, the reglementary-dose CHI was found to induce MetS in mice by regulating the gut microbiota and BAs metabolism via the FXR signaling pathway. This study provides evidence linking the gut microbiota and pesticides exposure with the progression of MetS, demonstrating the key role of gut microbiota in the toxic effects of pesticides.

The enantioselective toxicity of triticonazole (TRZ) to non-target organisms, the effect on wheat growth and quality, and the environmental fate of TRZ were investigated systematically in this study. The acute toxicity of S-TRZ to non-target aquatic and terrestrial organisms was greater than that of rac-TRZ and R-TRZ. The S-enantiomer significantly inhibited the growth and lodging resistance of wheat. S- and R-TRZ not only reduced the grain yield but also inhibited the activities of ADP-glucose pyrophosphorylase (AGPase) and starch synthase. The results of homology modeling and molecular docking further showed that the inhibition of AGPase activity by the two enantiomers hindered the accumulation of starch. By contrast, the racemate promoted the growth and development of wheat and improved grain quality. And the half-lives of the racemate in stems, grains, leaves, and soils were shorter than those of the enantiomers. The results of risk quotient (RQ) values showed that the application of TRZ enantiomers during wheat planting would bring a higher potential dietary risk to Chinese consumers. In comprehensive consideration of these results, the application of the racemate may be safer and more reasonable at the flowering stage of wheat.

Decabromodiphenyl ethane (DBDPE) as a novel brominated flame retardant is frequently detected in environmental media due to its widespread use. Studies have shown that exposure to environmental pollutants in utero could lead to weight loss in newborns and obesity in adulthood. However, the mechanisms of how the cubs grow rapidly from low birth weight to obesity remain unclear. Although it has been reported that perinatal DBDPE exposure caused obesity in the offspring of mice in adulthood, its metabolic changes in offspring juvenile are unknown. Here, we monitored changes of body weight in cubs following exposure to DBDPE in utero. Furthermore

Imazalil (IMZ) is a highly effective fungicide employed in crop production. It has been consistently detected in aquatic environments. The main environmental metabolite of IMZ is imazalil-M (IMZ-M). Limited studies have focused on the toxicity of IMZ and IMZ-M in aquatic organisms. This study systematically evaluated the developmental toxicity of IMZ and IMZ-M on zebrafish (Danio rerio) embryos and explored the potential mechanisms involved. The results showed that IMZ and IMZ-M caused developmental toxicity, characterized by decreased heart rate, hatching inhibition, and pericardial cyst in zebrafish embryos. Subsequently, acridine orange (AO) staining revealed cell apoptosis in the area around the heart regions of zebrafish larvae. Besides, the expression levels of apoptosis-related genes also varied significantly. Furthermore

The environmental risks of prothioconazole (PTC), a popular agricultural fungicide, and its main metabolite, prothioconazole-desthio (PTCd), have attracted more and more attention recently. In this study, the adverse effects of PTC and PTCd on liver function in mice and their underlying mechanisms have been systematically studied from the perspective of gut microbiota. Combining the results of physiological, biochemical, and histopathological analysis showed that PTC and PTCd exposure could cause lipid accumulation and inflammation in the liver of mice. In addition, exposure to PTC and PTCd could also significantly affect the transcriptome of liver tissue, leading to disorders of lipid metabolism of the liver. Particularly, the abundances of bacteria in liver tissues were significantly increased with PTC and PTCd exposure. Further results show that PTC and PTCd could affect the expression of genes related to inflammation and the barrier function in colon tissue, leading to intestinal dysfunction in mice. Last but not least, the results based on 16S rRNA gene sequencing and 1H NMR metabolomics analysis showed that exposure to PTC and PTCd could cause gut microbiota imbalances and cecal content metabolic profile disorders. In short, this study found that PTC and PTCd exposure could cause liver damage in mice by changing the gut microbiota, disrupting the intestinal barrier function and promoting bacterial translocation. These results clarified the key role of gut microbiota in liver damage induced by PTC and PTCd in mice and proposed a new insight into the mechanisms of liver toxicity induced by pesticides through the dialogue of the gut-liver axis.

Prothioconazole (PTA), a new triazole fungicide, has been widely used worldwide. A recent study has confirmed that PTA and its main metabolite prothioconazole-desthio (dPTA) interfere with the liver metabolism in reptiles. However, little is known about liver toxicity of these two pollutants in mammals. Here, female mice were orally exposed to PTA (1.5 mg/kg body weight/day) and dPTA (1.5 mg/kg body weight/day) for 30 days. Additionally, growth phenotype and indexes related to serum and liver function were examined. Using metabolomics and gene expression analysis, PTA- and dPTA-induced hepatotoxicity was studied to clarify its potential underlying mechanism of action. Together, the results indicated that PTA and dPTA exposure caused changes in growth phenotypes, including elevated blood glucose levels, triglyceride accumulation, and damage of liver function. Additionally, exposure to PTA and dPTA caused changes in genes and metabolites related to glycolipid metabolism in female mice, thereby interfering with the pyruvate metabolism and glycolysis/gluconeogenesis pathways, ultimately leading to hepatic metabolism disorders. In particular, the effect of dPTA on hepatotoxicity has been proven to be more significant than that of PTA. Thus, these findings help us understand the underlying mechanism of action of PTA and dPTA exposure-induced hepatotoxicity in mammals and possibly humans.

Reptiles are an important part of vertebrates and are the primitive terrestrial vertebrates. However, lots of reptile species are endangered or susceptible to extinction. It is no doubt that contaminants are one of the important reasons for the decline of the lizard population. In this study, the selective metabolism of triadimenol (TN) in the male Eremias argus lizards and the toxic effects of TN on lizards were studied. TN chiral isomers were separated and detected by HPLC-MS/MS system with Lux Cellulose-1 column. Tissue distribution experiments showed the existence of stereoselectivity biotransformation of TN enantiomers among organs in lizards, and RR-TN preferentially emerged over the other enantiomers. The antioxidant enzymes (SOD, CAT, GST) activities and MDA content assays demonstrated that TN induced oxidative stress in most organs, especially in the liver, and the histopathology analysis showed the severe liver and testis damage caused by 14-day continuous TN gavage. The reproductive effects of TN-induced reflected in the increased sex hormone testosterone. This research confirms that TN could induce hepatic and reproductive toxicity of E. argus lizard.

Enantiomers of chiral pesticides usually display different toxic effects on non-target organisms in surrounding environment, but there are few studies on its enantioselective toxicity of paclobutrazol to aquatic organisms such as Chlorella vulgaris (C. vulgaris). In this study, the enantioselective bioaccumulation and toxicities, such as acute toxicity and oxidative stress, of the racemate, (2S, 3S)-enantiomer (S-enantiomer) and (2R, 3R)-enantiomer (R-enantiomer) of paclobutrazol to the C. vulgaris cells were investigated. The results showed that the algae cells were able to accumulate the paclobutrazol in a short time, while this bioaccumulation had no enantioselective distinction between the two enantiomers during biological metabolism. However, the racemate and two enantiomers of paclobutrazol significantly inhibited the growth of C. vulgaris, displayed different median lethal concentrations. The photosynthetic pigments, photosynthesis-related genes as well as antioxidation-related biomarkers in treated C. vulgaris were also investigated. In general, R-enantiomer was found to be more toxic to C. vulgaris cells than its racemate and S-enantiomer. Additionally, transmission electron microscopy (TEM) analysis showed the R-enantiomer caused more serious changes than S-enantiomer. Moreover, contents of two plant hormones (gibberellin, GA and indoleacetic acid, IAA) were determined in treated C. vulgaris. Higher paclobutrazol concentrations caused lower IAA contents significantly. Nevertheless, the two enantiomers showed no enantioselective effects on the biosynthesis of GA in C. vulgaris. Our results are helpful to understand the enantioselective effects of paclobutrazol enantiomers on non-target organisms, and useful for evaluating their environmental risks.

Pesticides are proposed as one of the many causes for the global decline in reptile population. To understand the potential impact of alpha-cypermethrin (ACP) in reptiles, in the current study, we used a tri-trophic food web (plants - herbivores - natural enemies of predators) to examine the reproductive toxicity and biomarker changes. Based on the Maximum Residue Limit (MRL) of ACP in several agricultural products, we designed three concentrations 0, 2 (MRL), and 20 mg/kg wet weight as three treatment groups for this research. Male and female lizards were fed ACP contaminated or uncontaminated diets for eight weeks during the breeding phase. The number of deaths was different among the three groups, and a dose-dependent trend was found. Decreases in food consumption of 26.6% and 28.1% were observed in the low- and high-dose group, respectively. Dietary exposure significantly induced a dose-dependent decrease in body mass index in lizards. Significant variations in glutathione-S-transferaseb activities, catalase activities, and malondialdehyde levels in gonads, suggest that lizards were under oxidative stress. In addition, ACP exposure altered sexual hormone levels in males, reduced reproductive output of females, and induced histopathological changes in testes. These negative effects highlight that ACP dietary exposure is a potential threat to lizards’ reproduction.

Numerous studies suggested that reptiles are sensitive to environmental pollution and the abundance of many species are in decline. Our research is aim to assess the toxic effects of pesticide in reptiles. And we also want to supply some data about nondestructive samples for environmental risk assessment in reptiles. Lizards were orally administered a single-dose of beta-cypermethrin (BCP) or myclobutanil (MC) at the concentration of 20 mg/kg body weight (bw). The results showed that pesticides could induce changes in enzymatic activities (SOD, CAT, LDH, AChE) and MDA levels in organs or tissues of lizards. BCP could cause more severe oxidative damage than that of MC. Salivary enzymes activities showed sensitivity changes to the toxicity of pesticides. We could use saliva to reflect whether the reptiles are toxic by pesticides. We also agree that buccal swabs could be used as a tool for saliva sampling.

Chemical pollution and global warming are two major threats to organisms, which can interact to affect the normal activities of living beings. In this study, to explore the effects of abamectin and high temperature on adaptability of lizard, male adult Eremias argus (a native Chinese lizard) were exposed to environmentally relevant concentrations of abamectin (0.02 mg·L

Risk assessments of the ecotoxicological effects insecticides impose on ectotherms have increasingly considered temperature. However, the changes toxicants induce in thermoregulatory behavioral traits may lead to a divergence of thermal selection and temperature-dependent changes of contaminant toxicity. This study demonstrated the interaction of behavioral thermoregulation and temperature-dependent toxicity of beta-cyfluthrin (BC) in the lizard Eremias argus. Based on the negative relationship between temperature and BC toxicity, seeking a warming environment was assumed to represent a self-rescue behavior (and vice versa). The results showed that BC-treated lizards (0–20 μg/g body weight (bw)) showed such self-rescue behavior, while lizards exposed to an extremely high BC dose (200 μg/g bw) sought a cooler environment. Biochemical assays showed that BC affected neurotransmitter systems, caused oxidative stress, and interfered with ion-transport in the central nervous system. Biomarkers of the cholinergic and glutamatergic system, ion-transport function, and oxidative stress were identified as potential biochemical variables related to thermoregulatory behavior. Apparently, seeking a warmer environment is a survival strategy with the aim to neutralize BC toxicity, while seeking a cooler environment aims to attenuate the harmful effects of metabolic and oxidative stress, and to decelerate internal BC diffusion. This phenomenon could be also explained by the concept of the “cooling trap”, i.e., a behavior where cooler temperatures are sought. This impairs survival after exposure to BC at it has a negative temperature coefficient, derived from a dysfunction of the central nervous system regarding thermoregulation caused by the high dosage of neurotoxicant and resulting temperature maladaptation. Implications of the interaction between thermoregulatory behavior and temperature-dependent toxicity are presented, which may aid further temperature-dependent risk assessments.

In this study, the stereochemistry, stereoselective fungicidal bioactivity, and antifungal mechanism of chiral triazole fungicide metconazole were investigated. The configurations of metconazole stereoisomers were determined to be (1R, 5R)-metconazole, (1R, 5S)-metconazole, (1S, 5S)-metconazole, and (1S, 5R)-metconazole through using electronic circular dichroism spectroscopy. The bioactivities of four stereoisomers and their stereoisomer mixture toward Fusarium graminearum Schw and Alternaria triticina were found to be in the following order: (1S, 5R)-metconazole > the stereoisomer mixture > (1S, 5S)-metconazole > (1R, 5R)-metconazole > (1R, 5S)-metconazole. In addition, the fungicidal activities of (1S, 5R)-metconazole against two tested pathogens was 13.9–23.4 times higher than those of (1R, 5S)-metconazole. Molecular docking methodology was applied to characterize the docking energy and distances between Cytochrome P450 CYP51B and the metconazole stereoisomers, and (1S, 5R)-metconazole showed the strongest binding energy and the shortest distance binding to CYP51B than the other three stereoisomers. Moreover, enantioselective metabolisms of (1S, 5R)-metconazole and (1R, 5S)-metconazole by Fusarium graminearum Schw were investigated through NMR-based metabolomics. The amounts of alanine, arginine, acetate, ethanol, and dimethylamine produced in the presence of (1R, 5S)-metconazole were significantly higher than corresponding amounts in the presence of (1S, 5R)-metconazole, whereas the amounts of glucose, glycerol, glutamate, methionine, and trimethylamine formed in the presence of (1R, 5S)-metconazole were much less than those in the presence of (1S, 5R)-metconazole. This systematic investigation of metconazole stereoisomers would provide a new perception of metconazole in stereoisomeric level, including bioactivities, metabolic behaviors and antifungal mechanism.

Plant growth can be influenced by the application of triazole pesticides as these regulate physiological processes such as plant hormonal levels and enzyme activity. Homology modeling and molecular docking studies suggested that inhibition of ADP-glucose pyrophosphorylase activity in two trans-stereoisomers treatments hinders starch accumulation during the grain filling stage. A field experiment investigated the effects of metconazole racemate, cis-1R,5S-stereostereoisomer, and cis-1S,5R-stereoisomer application at the flowering stage on wheat grain ripening and yield. The concentrations of racemate and both cis-stereoisomers were detected in wheat plant and grain samples. Compared with the racemate, both cis-stereoisomers were more persistent in the matrices. Treatment with cis-1R,5S-stereoisomer decreased grain weight and yield of wheat by delaying chlorophyll degradation, increasing the ethylene content, and decreasing the level of abscisic acid. The germination of harvested seeds was adversely affected by racemate treatment as a result of gibberellin and abscisic acid metabolism regulation and the transcription of signaling-related genes. Therefore, cis-1S,5R-stereoisomer was recommended to be used as metconazole pesticide at the flowering stage.

Hibernation is a short-term survival strategy for ectotherms to cope with cold weather and food shortages. The energy sources stored before hibernation are used not only in the winter, but also in preparation for reproduction. Reproductive physiology and behavior are primarily regulated by the hypothalamus-pituitary-gonad (HPG) axis. In this study, we examined endocrine hormone changes in the HPG axis of female lizards (Eremias argus) after chlorantraniliprole insecticide (CAP) exposure during hibernation. The levels of gonadotropin-releasing hormone, luteinizing hormone, follicle-stimulating hormone and progesterone were significantly decreased and the level of testosterone (T) was significantly increased after 135d experiment. This study verified the possible endocrine disrupting effects of CAP. More energy material consumption was observed in CAP treated group. Female E. argus preferred to invest energy to present survival when exposed to CAP, rather than to reserve material for following reproductive activity.

In addition to their fungicidal activity, many triazole fungicides function as plant regulators, which might impose adverse effects on the growth and development of crops. For chiral triazole fungicides, these effects can be alleviated by applying stereoisomers with high fungicidal and low regulator activities. This study investigated the stereoselectivity of four stereoisomers and the racemate of metconazole (2.5 g/100 kg seeds) on emergence and growth of seedlings (BBCH 01-14) in wheat. Wheat seedlings, coated with cis-1S,5R-metconazole, had a significantly lower seedling emergence ratio and shoot length than other metconazole treatments; however, the opposite effects were observed in the trans-1S,5S-metconazole treatment. With regard to the hormonal level, enzyme activity, and gene transcription of gibberellin (GA) and jasmonic acid (JA), cis-1S,5R-metconazole treatment inhibited GA biosynthesis while trans-1S,5S-metconazole treatment promoted GA biosynthesis. Moreover, cis-1S,5R-metconazole, trans-1S,5S-metconazole, trans-1R,5R-metconazole, and racemate treatments increased JA biosynthesis. The oxidative stress responses in trans-1R,5R-metconazole and racemate treatments were more intensive. Therefore, compared with the control, treatment with cis-1R,5S-metcoanzole exhibited minimal influence on wheat seedling growth. The results showed that the application of pure cis-1R,5S-metcoanzole (instead of the racemate) in agricultural management could decrease the risks associated with crop growth and developmental damage.

The residue of simazine herbicide in the environment is known as one of pollutant stress for lizards by crippling its fitness on direct toxic effects and indirect food shortage via the food chain effects. Both stressors were considered in our experiment in the simazine exposure and food availability to lizards (Eremias argus). The results revealed that starvation significantly reduced the lizard's energy reserve and native immune function, while the accumulation of simazine in the liver was significantly increased. Simazine caused oxidative stress in the liver of lizards, but oxidative damage only occurred in the starved lizards. Simazine also changed the energy reserves, native immune function and detoxification of well-fed lizards, while the starved lizards showed different sensitivity to simazine. Simazine or starvation treatment independently activated the lizard HPA axis, but co-treatment caused the HPA axis inhibition. Besides, according to the variations on amino acid neurotransmitters, corticosterone hormone and thermoregulatory behavior, we inferred that lizards in threatens take the appropriate strategy on energy investment and allocation through neural, endocrine and behavioral pathways to maximize benefits in dilemma. Energy allocation was necessary, while suppression on any physiological process comes at a cost that is detrimental to long-term individual fitness.

Although many toxicological studies on pesticides and nanoparticles have been conducted, it is not clear whether nanoparticles will increase the toxicity of pesticides. In this study, we chose imidacloprid (IMI) as a representative pesticide, and explored the influence of ZnO NPs on the toxic effect of IMI. In addition, we studied the bioaccumulation of IMI in mice. Using biochemical index analysis, liver histopathological analysis, non-targeted metabolomics, and LC/MS analysis, we found that ZnO NPs increased the toxicity of IMI, which may be related to the increase in IMI bioaccumulation in mice. In addition, we used intestinal histopathological analysis, RT-qPCR, and 16sRNA sequencing to find that the disturbance of the gut microbiota and the impaired intestinal barrier caused by ZnO NPs may be the reason for the increase in IMI bioaccumulation. In summary, our results indicate that ZnO NPs disrupted the intestinal barrier and enhanced the bioaccumulation of IMI, and therefore increased the toxicity of IMI in mice. Our research has deepened the toxicological insights between nanomaterials and pesticides.

The environmental contaminant, especially pesticides, threatened the amphibian population. In this assay, the enantioselective behavior of cyproconazole on Rana nigromaculata was studied. We found LC50 (lethal concentration causing 50% mortality) of 4-enantiomers was nearly twice as 3-enantiomers in 96 h acute toxicity test. Besides, the significant considerable variation of oxidative stress and LDH (lactic dehydrogenase) induced by the four enantiomers indicated that cyproconazole could enantioselectively affect enzymes in tadpoles. Bioaccumulation experiments showed the order of cyproconazole in the tadpoles was 4-enantiomers>3- enantiomers>2- enantiomers>1- enantiomers during the exposure for 28d. In tissue distribution test, cyproconazole was formed and accumulated in order of 4-enantiomers>2-enantiomers>3- enantiomers>1- enantiomers, except that in the gut. During the elimination experiment, cyproconazole was rapidly eliminated by 95% within the only 24 h. These results suggested that the influence of enantioselective behavior should consider when assessing ecological risk of chiral pesticides to amphibians.

Pesticides are one of major causes for amphibian population declines and the behavior of pesticide metabolite products to amphibians has become a rising concern. In this study, the acute toxicity and the chronic effects of triadimefon and triadimenol (the metabolite of triadimefon) on Rana. nigromaculata were investigated. In the acute assay, significant differences were observed in antioxidant enzyme activities and malondialdehyde levels between the triadimefon and triadimenol. The 96 h-acute toxicity of triadimefon (25.97 mg/L) and triadimenol (34.55 mg/L) to tadpoles was low. In 28d-chronic exposure, we studied the relative expression of tadpoles genes related to thyroid hormone-dependent metamorphic development, histological examination of liver and some biological index, including wet weight, snout-to-vent length (SVL) and development stages. The results revealed that the effects of triadimefon and triadimenol on tadpole development are driven by a disruption of the hormonal pathways involved in metamorphosis. Interestingly, triadimefon was more harmful on R. nigromaculata than triadimenol at high dose, whereas the reverse result was observed at low doses. According to the relative expression of thyroid hormone-dependent genes, we also found that the two compounds may have different mechanisms of toxic action on R. nigromaculata. Our study developed a pragmatic approach for use in the risk assessment of pesticide and its metabolite，and increased the information and understanding of the impacts of fungicides and other potential endocrine disrupting environmental contaminants on amphibians.

Hexachlorocyclohexane isomers (HCHs) are persistent organic pollutants (POPs), having potential risks to humans and ecosystem. This work evaluated the propensity of organisms to accumulate, eliminate, and transfer HCHs along the food chain (Tubifex tubifex and common carp (Cyprinus carpio)). The accumulation of HCHs from water by worms and carp was observed, and the concentrations increased with exposure time. After 8 days, the HCH concentrations in organisms remained stable. The accumulation factor (AF) values of HCHs in T. tubifex were higher than those in carp, indicating that the bioaccumulation abilities of HCHs in T. tubifex were higher than those in carp. The contaminated worms as a dietary source in the food chain led to significantly higher bioaccumulation in carp. The biomagnification factor (BMF) values of HCH isomers were all greater than 1. In the dissipation experiments, the elimination was fast and the half-lives were shorter than 2.5 days. The enantioselective accumulation and dissipation of α-HCH enantiomers were observed in worms and carp (food chain), and the enantiomeric differences should be taken into consideration in the study of contaminants risk assessment. The results on trophic transfer of HCHs in a freshwater food chain should be helpful for better understanding the fate, transport, and transfer of HCHs in freshwater environments.

Pesticides are a major cause of the reduction in the global amphibian population. In this study, the acute toxicity and chronic effects of metamifop on Xenopus laevis (X. laevis) tadpoles were investigated. The 96 h-LC50 value of metamifop on X. laevis tadpoles was 0.634 mg/L, which indicated that metamifop was highly toxic to tadpoles. In the chronic toxicity study, tadpoles were exposed to 0.063 mg/L of metamifop. After 14, 21 and 35 d of exposure, metamifop significantly inhibited the body weight and neurotransmitter synthesis of tadpoles, caused abnormal behavior and interfered with fat metabolism. According to the results of antioxidant enzymes and malondialdehyde (MDA), tadpoles exposed to 0.063 mg/L metamifop suffered severe lipid oxidative damage. Compared with the control group, the thyroid hormone (TH) levels and related gene expression in tadpoles in the treatment group were affected, reflecting the endocrine interference effect of metamifop. The data of this study can enrich our knowledge of the effects of aryloxyphenoxy propionate pesticides on amphibians and highlight the role of metamifop and other pesticides play in global decline of amphibians.

Agricultural source pollution has been hypothesized as one of the main reasons for reptile declines over recent decades. In addition to their direct toxicity to reptiles, agrochemicals can also enter complex interactions with environmental factors, which alter the interspecific relationships within communities. The potentially resulting cascading effects affect our understanding of the links between contaminants and the extent of declines of reptile species. In the present study, plant-arthropod-lizard tritrophic microcosms were assessed to identify the ecological effect of the widely used herbicide simazine in simulated steppe ecosystems. Three dosages of simazine (0, 0.060, and 0.006 g a.i./m2) were applied to microcosms, and the responses of organisms at three trophic levels were examined after 30-day exposure. The results showed that simazine could inhibit the growth and ecological functions of primary producers, and caused a reduction in the content of primary and secondary metabolites. The number of arthropod populations decreased in the lower simazine application but increased in the higher simazine application, compared with the control. Simazine led to slow growth and poor physical conditions in lizards. The impact of simazine on the community could be attributed to the following three aspects: (1) a direct effect of simazine, (2) the driving force of food resources, and (3) behavioral dynamics. The physical conditions of lizards and of the arthropod population in the microcosms showed different responses to standard toxicological tests, and the forces of cascading causalities were identified as the main factors beyond the direct simazine toxicity. Therefore, the propagation and cascade across multitrophic levels should be considered in future assessments to avoid distorting conclusions.

In recent years, serious environmental pollution has caused a decrease in the abundance of many species worldwide. Reptiles are the most diverse group of terrestrial vertebrates. There are large amounts of toxicological data available regarding myclobutanil, but the adverse effects of myclobutanil on lizards has not been widely reported. In this study, treatment groups were orally administered a single-dose of myclobutanil (20 mg/kg body weight (bw)). Subsequently, it was found that there were differences in myclobutanil levels between the different tissues and concentrations also changed with degradation time. The tissue concentrations of myclobutanil decreased in the order of: stomach > liver > lung > blood > testis > kidney > heart > brain. Based on our results, the liver and testis were considered to be the main target organs in lizards, indicating that the myclobutanil could induce potential hepatic and reproductive toxicity on lizards. Meanwhile, it was also demonstrated that the toxic effects of myclobutanil was different in different species, and the distribution of different pesticides in lizards were different.

Soil contamination caused by the widespread use of pesticides is one of the main environmental problems facing conservation organizations. (S)-metolachlor (SM) is a selective pre-emergent herbicide that poses potential risks to soil-related organisms such as reptiles. The present study elucidated the toxic effects of SM (3 and 30 mg/kg soil weight) in Eremias argus. The results showed that growth pattern was similar between the sexes in breeding season. For males, both kidney coefficient (KC) and testis coefficient in the exposure group were significantly different from those in the control group, while only KC in the high-dose group was significantly higher for females. Based on histopathological analysis, the livers of female lizards were more vulnerable than those of males in the exposure group. A reduction in total egg output was observed in SM exposed lizards. Accumulation studies indicated that skin exposure may be an important route for SM uptake in E. argus, and that the liver and lung have strong detoxification abilities. In addition, the body burdens of the lizards increased with increasing SM concentration in the soil.

Efficacy and potential environmental risks should be considered when applying enantiopure pesticides. In this study, Tubifex tubifex and its oxidative stress biomarkers were assessed for the toxicity of metalaxyl and metalaxyl-M in sediment. The toxicity assessment was conducted with artificial sediment and reconstituted water. Five test concentrations (from 0 to 100 mg/kg) were set for the short-term (4 days) exposure. The long-term (28 days) exposure was conducted with the environmental concentration (from 0.5 to 5 mg/kg). For the short-term exposure, the increase of superoxide dismutase (SOD) activity was observed, and a clear concentration-response relationship was found in the metalaxyl treatments. The decrease of catalase (CAT) and glutathione peroxidase (GPx) activity could be caused by oxidative stress. The decrease of glutathione (GSH) content and the increase of glutathione-S-transferase (GST) might be due to antioxidation defense and detoxification mechanisms. The increase of malondialdehyde (MDA) might be due to the saturation of antioxidant systems and the accumulation and toxicity of contaminations. In the long-term exposure, the changes of biomarkers in T. tubifex reflected the oxidative stress and detoxification metabolisms. GSH and the related enzymes were important in detoxification processes and involved in the oxidative stress in toxicity mechanism. The long-term direct contact bioassay is sensitive and appropriate to reflect the lower concentration of contaminants.

Benalaxyl is widely applied as a fungicide during grape planting processing. In this experiment, the stereoselective behavior of benalaxyl was studied during the grape growth and wine-making process. A simple method based on high-performance liquid chromatography (HPLC) equipped with a chiral column and UV detector was established to separate and determine the enantiomers of benalaxyl. Stereoselective degradation of the two enantiomers of benalaxyl was found in grapes. The degradation of both enantiomers followed pseudofirst-order kinetics, and the degradation rate of R-(−)-benalaxyl was faster than S-(+)-benalaxyl. The half-life of R-(−)-benalaxyl was 27 h, while the half-life of S-(+)-benalaxyl was 31 h. The enantiomer fraction value decreased from 0.50 to 0.34 and finally only S-(+)-benalaxyl could be detected. In the fermentation process, both enantiomers of benalaxyl were hardly degraded, and no configuration interconversion was observed. Meanwhile, both enantiomers of benalaxyl showed little influence on the growth of the yeast, consumption of carbon sources, or production of alcohol. The result of this study might provide more sufficient data for the evaluation of food safety and potential risk. Chirality 00:000–000, 2016. © 2016 Wiley Periodicals, Inc.

In this study, Tubifex tubifex (Oligochaeta, Tubificida) was exposed to hexachlorocyclohexane isomers (α-HCH, β-HCH and γ-HCH) in an aquatic environment to study the bioaccumulation and elimination of these chemicals in this organism. Rapid and linear accumulation processes with high accumulation factor values (AFs) were found during the 14 d water exposure, and there were no significant differences among the concentrations of HCH isomers. The unsteady state (linear shape) might be due to the change of feeding physiology of tubifex. The AFs of α-HCH were significantly different from those of β-HCH, which may be due to different physicochemical properties. Furthermore, no enantioselective bioaccumulation of α-HCH enantiomers was found in tubifex tissue. The data from elimination experiments fitted a typical first-order kinetics model. The elimination rates (ke) decreased with increasing hydrophobicity (Kow) for HCHs. If evaporation was not considered, the majority of HCHs were metabolized by tubifex. So the existence of worms and their biotransformation ability could change the distribution of HCHs in the aquatic environment and reduce the surrounding HCHs levels, which is significant in environmental pollution control. This study also assessed the responses of biochemical biomarkers. Increased superoxide dismutase (SOD) and malondialdehyde (MDA) levels demonstrated the presence of oxidative stress in worms. The different changes of catalase (CAT) activities depend on many factors, and there are other enzymes involved in H2O2 catabolism. Additionally a reduction of glutathione-S-transferase (GST) was observed indicating the toxic impacts of HCHs. Our results suggested that bioaccumulation of HCHs in T. tubifex can cause sublethal toxicity. T. tubifex could reflect the HCHs contaminant concentrations in the environment to some extent, and the worms may be proposed as biomarkers to characterize water contamination.

Amphibians are the most endangered class of vertebrates. In this study, Xenopus laevis frogs were exposed to 0, 1 and 10 mg/L of triadimefon or triadimenol. After 14 or 28 days of exposure, high levels of triadimefon or triadimenol obstructed the growth of frogs. However, low levels of triadimefon induced the growth of females after the longer period of exposure. We also found that the antioxidant enzyme activity and LDH levels in males were higher than those in females after 28-days exposure. In histopathology tests, triadimenol exerted more effect on the ovary while triadimefon exerted more effect on the testes. Additionally, the levels of Estradiol in all 14-day treatments, except 1 mg/L triadimenol, were significantly decreased, however, there was no difference in testosterone levels. Furthermore, triadimefon and triadimenol disrupted the expression of genes controlling hormone homeostasis and reproduction, and this effect depended on the exposure time and the gender of the organism. Our experiments explored the effect of triadimefon and its metabolite on the gonads of frogs and highlighted the role that pesticides are likely to play in the global decline of amphibians.