Rhodococcus antarcticus sp. nov., isolated from a till sample of Collins glacier front, Antarctica.

A pink-coloured, Gram-stain-positive, aerobic and rod-shaped strain, designated 75T, was isolated from Collins glacier front till, Antarctica. Strain 75T was non-motile and non-spore-forming. Growth was observed at pH 6.0-9.0 (optimum, pH 7.0), at 4-45 °C (optimum, 20 °C) and with 0-9 % (w/v) NaCl (optimum, 1%). Phylogenetic analyses based on 16S rRNA gene sequences showed that strain 75T belongs to the genus Rhodococcus, and is related to Rhodococcus gannanensis DSM 104003T, Rhodococcus aerolatus KCTC29240T and Rhodococcus agglutinans KCTC 39118T (96.1, 96.0 and 95.7 % sequence similarity, respectively). The main polar lipids were identified as diphosphatidylglycerol, phosphatidylglycerol, phosphatidylethanolamine, phosphatidylinositol, phosphatidylinositol mannoside and a phosphoglycolipid. The major cellular fatty acids were identified as C16 : 0, iso- C16 : 0, 10-methyl C17 : 0 and C17 : 1 ω8c. MK-7 and MK-8(H4) were found to be the dominant menaquinones. Whole-cell hydrolysates contained meso-diaminopimelic acid, ribose, galactose, glucose and rhamnose. The genome of strain 75T is 3.82 Mb long in size with a G+C content of 73.1 mol%. On the basis of phenotypic, molecular and chemotaxonomic characteristics, strain 75T is considered to represent a novel species of the genus Rhodococcus, for which the name Rhodococcus antarcticus sp. nov. is proposed. The type strain is 75T (=CCTCC AA 2019032T=KCTC 49334T).

Paraconexibacter antarcticus sp. nov., a novel actinobacterium isolated from Antarctic tundra soil.

A Gram-negative, non-motile, aerobic bacterium, named 02-257T, was isolated from Antarctic soil. The cells are surrounded by relatively thin capsules and were catalase-positive and oxidase-negative cocci. Growth of strain 02-257T was observed at 4-35 °C (optimum, 28-30 °C), pH 6.0-8.0 (optimum, pH 6.0) and with 0-1.5% NaCl (optimum, 0 %). Strain 02-257 showed the highest 16S rRNA gene sequence similarity to Paraconexibacter algicola Seoho-28T (95.06 %). Phylogenetic analysis based on 16S rRNA gene sequences indicated that strain 02-257T is a member of a novel species belonging to the clade formed by members of the genus Paraconexibacter in the family Paraconexibacteraceae. The DNA G+C content was 72.9 mol%. Strain 02-257T contained C16 : 0-iso (23.0 %), C18  :  1 ω9c (13.8 %), C16 : 0 (12.5 %) and C17 : 1 ω9c-iso (10.8 %) as major cellular fatty acids and menaquinone MK-7(H4) was detected as the only isoprenoid quinone. Diphosphatidylglycerol, phosphatidylinositol, phosphatidylinositole mannoside, phosphatidylinositole dimannoside, unidentified phosphoglycolipid, unidentified aminophospholipid, two unidentified phospholipids, three unidentified aminolipids and six unidentified lipids were the major polar lipids. meso-Diaminopimelic acids were the diagnostic diamino acids in the cell-wall peptidoglycan. On the basis of phenotypic, chemotaxonomic and phylogenetic data, strain 02-257T is considered to represent a novel species of the genus Paraconexibacter, for which the name Paraconexibacter antarcticus sp. nov. is proposed. The type strain is 02-257T (=CCTCC AB 2021030T=KCTC 49619T).

Degradation of Glyphosate by Mn-Oxide May Bypass Sarcosine and Form Glycine Directly after C-N Bond Cleavage.

Glyphosate is the active ingredient of the common herbicide Roundup. The increasing presence of glyphosate and its byproducts has raised concerns about its potential impact on the environment and human health. In this research, we investigated abiotic pathways of glyphosate degradation as catalyzed by birnessite under aerobic and neutral pH conditions to determine whether certain pathways have the potential to generate less harmful intermediate products. Nuclear magnetic resonance (NMR) spectroscopy and high-performance liquid chromatography (HPLC) were utilized to identify and quantify reaction products, and density functional theory (DFT) calculations were used to investigate the bond critical point (BCP) properties of the C-N bond in glyphosate and Mn(IV)-complexed glyphosate. We found that sarcosine, the commonly recognized precursor to glycine, was not present at detectable levels in any of our experiments despite the fact that its half-life (∼13.6 h) was greater than our sampling intervals. Abiotic degradation of glyphosate largely followed the glycine pathway rather than the AMPA (aminomethylphosphonic acid) pathway. Preferential cleavage of the phosphonate adjacent C-N bond to form glycine directly was also supported by our BCP analysis, which revealed that this C-N bond was disproportionately affected by the interaction of glyphosate with Mn(IV). Overall, these results provide useful insights into the potential pathways through which glyphosate may degrade via relatively benign intermediates.

Isolation and Characterization of an Endophytic Fungal Strain with Potent Antimicrobial and Termiticidal Activities From Port-Orford-Cedar.

Termites are responsible for an estimated US$1 billion annually in property damage, repairs, pest control, and prevention. There is an urgent need of finding a better alternative way to control and prevent termites. Port-Orford-Cedar (POC) has been known to have significant levels of natural durability and termiticidal activities due to its extractive contents. In this study, 25 endophytes including 22 fungal and 3 bacterial strains were isolated from the POC. Four strains, namely, HDZK-BYF21, HDZK-BYF1, HDZK-BYF2, and HDZK-BYB11, were chosen to test their termiticidal activities. The fermentation broth of strain HDZK-BYF21 displayed the potent antimicrobial and termiticidal activities. Morphological examination and 18 S rDNA sequence analysis demonstrated that strain HDZK-BYF21 belonged to the genus Aspergillus. This finding indicates the existence of an interesting chemical symbiosis between an endophytic fungus and its host. This is also the first report on endophytes isolated from the POC that may have potential termiticidal activities. Endophytes with termiticidal activities can be grown in bioreactor to provide an inexhaustible supply of bioactive compounds and thus can be exploited commercially.

Acid-responsive polymeric nanocarriers for topical adapalene delivery.

PURPOSE: The acne skin is characteristic of a relatively lower pH microenvironment compared to the healthy skin. The aim of this work was to utilize such pH discrepancy as a site-specific trigger for on-demand topical adapalene delivery. METHODS: The anti-acne agent, adapalene, was encapsulated in acid-responsive polymer (Eudragit® EPO) nanocarriers via nanoprecipitation. The nanocarriers were characterized in terms of particle size, surface morphology, drug-carrier interaction, drug release and permeation. RESULTS: Adapalene experienced a rapid release at pH 4.0 in contrast to that at pH 5.0 and 6.0. The permeation study using silicone membrane revealed a significant higher drug flux from the nanocarrier (6.5 ± 0.6 µg.cm(-2).h(-1)) in comparison to that (3.9 ± 0.4 µg.cm(-2).h(-1)) in the control vehicle (Transcutol®). The in vitro pig skin tape stripping study showed that at 24 h post dose-application the nanocarrier delivered the same amount of drug to the stratum corneum as the positive control vehicle did. CONCLUSIONS: The acid-responsive nanocarriers hold promise for efficient adapalene delivery and thus improved acne therapy.

Chiral separation and enantioselective degradation of vinclozolin in soils.

Vinclozolin is a chiral fungicide with potential environmental problems. The chiral separation of the enantiomers and enantioselective degradation in soil were investigated in this work. The enantiomers were separated by high-performance liquid chromatography (HPLC) on Chiralpak IA, IB, and AZ-H chiral columns under normal phase and the influence of the mobile phase composition on the separation was also studied. Complete resolutions were obtained on all three chiral columns under optimized conditions with the same elution order of (+)/(-). The residual analysis of the enantiomers in soil was conducted using accelerate solvent extraction followed by HPLC determination. The recoveries of the enantiomers ranged from 85.7-105.7% with relative standard deviation (SD) of 0.12-3.83%, and the limit of detection (LOD) of the method was 0.013 µg/g. The results showed that the degradations of vinclozolin enantiomers in the soils followed first-order kinetics. Preferential degradation of the (-)-enantiomer was observed only in one soil with the largest |ES| value of 0.047, and no obvious enantioselective degradation was observed in other soils. It was found that the persistence of vinclozolin in soil was related to pH values based on the half-lives. The two enantiomers disappeared about 8 times faster in basic soils than that in neutral or acidic soils.

The chiral separation and enantioselective degradation of the chiral herbicide napropamide.

The chiral pesticide enantiomers often have different toxic effects and environmental behaviors, which suggests that the risk assessments should be on an enantiomeric level. In this work, the chiral separation of the napropamide enantiomers and the stereoselective degradation in tomato, cucumber, rape, cabbage, and soil were investigated. Napropamide enantiomers could be separated absolutely by high-performance liquid chromatography (HPLC) using a Chiralpak IC column with a resolution factor of 11.75 under the optimized condition. Solid phase extraction (SPE) was used for cleanup of the enantiomers in the vegetable samples. The residue analysis method was validated. Good linearities (R(2) = 0.9997) and recoveries (71.43% -97.64%) were obtained. The limits of detection (LOD) were 0.05 mg/kg in soil and 0.20 mg/kg in vegetables. The results of degradation showed that napropamide dissipated rapidly in vegetables with half-lives of only 1.13-2.21 days, but much more slowly in soil, with a half-life of 11.95 d. Slight stereoselective degradation of the two enantiomers was only observed in cabbage, with enantiomeric fraction (EF) = 0.46, and there was no enantioselectivity in the other vegetables. The degradation of napropamide in the five matrixes was fast, and there was no enantioselectivity.

Acute toxicity, bioactivity, and enantioselective behavior with tissue distribution in rabbits of myclobutanil enantiomers.

The enantioselective bioactivity against pathogens (Cercospora arachidicola, Fulvia fulva, and Phytophthora infestans) and acute toxicity to Daphnia magna of the fungicide myclobutanil enantiomers were studied. The (+)-enantiomer in an antimicrobial activity test was about 1.79-1.96 times more active than the (-)-enantiomer. In the toxicity assay, the calculated 24-h LC50 values of the (-)-form, rac-form and (+)-form were 16.88, 13.17, and 11.91 mg/L, and the 48-h LC50 values were 10.15, 9.24, and 5.48 mg/L, respectively, showing that (+)-myclobutanil was more toxic. Meanwhile, the enantioselective metabolism of myclobutanil enantiomers following a single intravenous (i.v.) administration was investigated in rabbits. Total plasma clearance value (CL) of the (+)-enantiomer was 1.68-fold higher than its antipode. Significant differences in pharmacokinetics parameters between the two enantiomers indicated that the high bioactive (+)-enantiomer was preferentially metabolized and eliminated in plasma. Consistent consequences were found in the tissues (liver, brain, heart, kidney, fat, and muscle), resulting in a relative enrichment of the low-activity (-)-myclobutanil. These systemic assessments of the stereoisomers of myclobutanil cannot be used only to investigate environmental and biological behavior, but also have human health implications because of the long persistence of triazole fungicide and enantiomeric enrichment in mammals and humans.

Recent Advanced Methods for Extracting and Analyzing Cannabinoids from Cannabis-Infused Edibles and Detecting Hemp-Derived Contaminants in Food (2013-2023): A Comprehensive Review.

Cannabis-infused edibles are food products infused with a cannabis extract. These edibles include baked goods, candies, and beverages, offering an alternative way to consume cannabis instead of smoking or vaporizing it. Ensuring the accurate detection of cannabis-infused edibles and identification of any contaminants is crucial for public health and safety. This is particularly important for compliance with legal regulations as these substances can have significant psychoactive effects, especially on unsuspecting consumers such as children or individuals with certain medical conditions. Using efficient extraction methods can greatly improve detection accuracy, ensuring that the concentration of cannabinoids in edibles is measured correctly and adheres to dosage guidelines and legal limits. This review comprehensively examines the preparation and extraction techniques for cannabinoid edibles. It covers methods such as solid-phase extraction, enhanced matrix removal-lipid, QuEChERS, dissolution and dispersion techniques, liquid-phase extraction, and other emerging methodologies along with analytical techniques for cannabinoid analysis. The main analytical techniques employed for the determination of cannabinoids include liquid chromatography (LC), gas chromatography (GC), direct analysis in real time (DART), and mass spectrometry (MS). The application of these extraction and analytical techniques is further demonstrated through their use in analyzing specific edible samples, including oils, candies, beverages, solid coffee and tea, snacks, pet food, and contaminated products.

Enantioselective kinetics of α-hexachlorocyclohexane in earthworm (Eisenia fedtia) and forest soil.

The enantioselective bioaccumulation and elimination behaviors of α-hexachlorocyclohexane (α-HCH) enantiomers in earthworm and soil were investigated by chiral gas chromatography. Enantiomer fraction values were calculated as indicators of the enantioselectivity. The mature earthworms were exposed to 0.10 µg g(-1)(wwt) (0.14 µg g(-1)(dwt)) spiked soil continuously for the bioaccumulation, and the elimination was conducted after an enrichment period in the soil. The results showed that both the bioaccumulation and elimination processes followed monophasic kinetics, body residues of α-HCH in earthworm increased to high level at the fifth day, and enantioselectivity was found in the bioaccumulation process with the rate constant (k) of 0.80 d(-1) for (+)-α-HCH and 0.74 d(-1) for (-)-α-HCH. The half life (t(1/2)) of the enantiomers obtained in the elimination process was within one day. The bioaccumulation factors of steady state of α-HCH enantiomers were 2.82 for (+)-α-HCH and 2.75 for (-)-α-HCH. The enantiomer fractions of earthworm and soil obviously below 0.5 during uptake and elimination processes indicate significant enantioselectivity and preferential depuration of (+)-α-HCH in earthworm. However, earthworms do not have a great capacity for getting rid of α-HCH in polluted soil shown by a contradistinctive experiment.

Role of metal complexation on the solubility and enzymatic hydrolysis of phytate.

Phytate is a dominant form of organic phosphorus (P) in the environment. Complexation and precipitation with polyvalent metal ions can stabilize phytate, thereby significantly hinder the hydrolysis by enzymes. Here, we studied the stability and hydrolyzability of environmentally relevant metal phytate complexes (Na, Ca, Mg, Cu, Zn, Al, Fe, Al/Fe, Mn, and Cd) under different pHs, presence of metal chelators, and thermal conditions. Our results show that the order of solubility of metal phytate complexes is as follows: i) for metal species: Na, Ca, Mg > Cu, Zn, Mn, Cd > Al, Fe, ii) under different pHs: pH 5.0 > pH 7.5), and iii) in the presence of chelators: EDTA> citric acid. Phytate-metal complexes are mostly resistant towards acid hydrolysis (except Al-phytate), and dry complexes are generally stable at high pressure and temperature under autoclave conditions (except Ca phytate). Inhibition of metal complex towards enzymatic hydrolysis by Aspergillus niger phytase was variable but found to be highest in Fe phytate complex. Strong chelating agents such as EDTA are insufficient for releasing metals from the complexes unless the reduction of metals (such as Fe) occurs first. The insights gained from this research are expected to contribute to the current understanding of the fate of phytate in the presence of various metals that are commonly present in agricultural soils.

Degradation of glyphosate and bioavailability of phosphorus derived from glyphosate in a soil-water system.

Glyphosate, the most commonly used herbicide in the world, can be degraded into more toxic and persistent products such as aminomethylphosphonic acid (AMPA) or non-toxic products such as sarcosine and glycine. In this study, we used liquid chromatography mass spectrometry (LC-MS) and electrospray ionization (ESI) source Q Extractive Orbitrap mass spectrometry (ESI-Orbitrap MS) to identify glyphosate degradation products and combined with sequential extraction and stable isotopes to investigate the degradation of glyphosate and transformation of phosphorous (P) product in a soil-water system. The LC-MS and ESI-Orbitrap MS results showed that glycine formed during the early stage but was rapidly utilized by soil microorganisms. AMPA started to accumulate at the late stage and was found to be 3-6 times more resistant than glyphosate against degradation; while no sarcosine was formed. The 18O labeling and phosphate oxygen isotope results allowed a clear distinction of the fraction of inorganic P (Pi) derived from glyphosate, about half of which was then rapidly taken up and recycled by soil microorganisms. Our results provide the first evidence of the preferential utilization of glyphosate-derived Pi by microorganisms in the soil-water system. The rapid cycling of Pi derived from this disregarded source has important implications on nutrient management as well as water quality.

Chiral quizalofop-ethyl and its metabolite quizalofop-acid in soils: Enantioselective degradation, enzymes interaction and toxicity to Eisenia foetida.

An enantioselective chromatographic method to analyze enantiomers of quizalofop-ethyl and its metabolite quizalofop-acid was established using a high-performance liquid chromatography (HPLC) on (R, R) Whelk-O 1 column. The enantioselective degradation kinetics of quizalofop-ethyl and quizalofop-acid in three soils were investigated. Moreover, the interaction with urease and catalase in the soils and the acute toxicity to Eisenia foetida of quizalofop-ethyl were also determined in order to assess their metabolism mechanism and environmental risk. From the results, quizalofop-ethyl was configurationally stable and was hydrolyzed rapidly to quizalofop-acid, which also degraded enantioselectively but slowly, and the inversion of the S-(-)-quizalofop-acid into the R-(+)-quizalofop-acid was observed in Xinxiang soil. In addition, quizalofop-ethyl and quizalofop-acid enantioselectively affected urease activity but not catalase. The acute toxicity assays to earthworm indicated that the racemic quizalofop-ethyl and quizalofop-acid were more toxic than quizalofop-p-ethyl and quizalofop-p-acid respectively, dramatically, the toxicity of the metabolite was much higher than the parent compound. These results revealed the enantioselective degradation of quizalofop-ethyl and quizalofop-acid, and the differences of toxicity among the enantiomers of the parent compound and the metabolite, which should be considered in future environmental risk evaluation.

Mechanisms of Bond Cleavage during Manganese Oxide and UV Degradation of Glyphosate: Results from Phosphate Oxygen Isotopes and Molecular Simulations.

Degradation of glyphosate in the presence of manganese oxide and UV light was analyzed using phosphate oxygen isotope ratios and density function theory (DFT). The preference of C-P or C-N bond cleavage was found to vary with changing glyphosate/manganese oxide ratios, indicating the potential role of sorption-induced conformational changes on the composition of intermediate degradation products. Isotope data confirmed that one oxygen atom derived solely from water was incorporated into the released phosphate during glyphosate degradation, and this might suggest similar nucleophilic substitution at P centers and C-P bond cleavage both in manganese oxide- and UV light-mediated degradation. The DFT results reveal that the C-P bond could be cleaved by water, OH- or •OH, with the energy barrier opposing bond dissociation being lowest in the presence of the radical species, and that C-N bond cleavage is favored by the formation of both nitrogen- and carbon-centered radicals. Overall, these results highlight the factors controlling the dominance of C-P or C-N bond cleavage that determines the composition of intermediate/final products and ultimately the degradation pathway.

Stereoselective quantitation of haloxyfop in environment samples and enantioselective degradation in soils.

The chiral separation of haloxyfop enantiomers was first performed on (R, R) Whelk-O1 chiral column (pirkle type) by high-performance liquid chromatography (HPLC). Chromatographic conditions such as mobile phase composition and column temperature were optimized, and the best resolution was obtained using hexane/n-propanol (98/2) with Rs value of 3.43. Chiral residue analysis methods for haloxyfop enantiomers in environmental matrices, such as soil and water, were developed with recoveries ranging from 85.95% to 104.25%. The results showed that these methods were effective enough for detecting the residual enantiomers environmental matrices. The behavior of haloxyfop in four soils was studied and the enantioselective degradation was found with enantiomer fraction values ranging from 0.058 to 0.61. The research work was extremely useful for investigating the fate of individual enantiomers in environment, the mechanism of the stereoselective behaviors, and the risk assessment of chiral pesticide.

Interplay of stimuli-responsiveness, drug loading and release for a surface-engineered dendrimer delivery system.

The objectives of this study were to generate novel thermo and pH dual responsive poly(amidoamine) (PAMAM) via precise surface engineering, and investigate the interplay of dendrimer stimuli-responsiveness and the loading and release properties of a model agent, vitamin E acetate (VEAc). A higher dendrimer generation and maximized VEAc loading at elevated pH all contributed to a lower cloud point (CP) of the dendrimer-VEAc complex. The drug loading in G3.5 surface-engineered PAMAM was 22 mol/mol (pH 7.0) and 10 mol/mol (pH 5.0), which corresponded to a complex CP value at ca. 13 °C (pH 7.0) and 46 °C (pH 5.0), respectively. At physiological conditions, only less than 40% of VEAc was liberated when reaching the plateau, whilst more than 90% of VEAc was released from such system within 6 h at pH 5.0. This was due to the transition of dendrimer surface from dehydrated state to hydrated state upon pH dropping, enabling rapid drug release for therapeutic action. This smart stimuli-responsive dendritic delivery system holds promise for the efficient drug delivery to tissues with pH abnormality such as tumor.

The effect of solute-membrane interaction on solute permeation under supersaturated conditions.

The purpose of this work was to investigate the effect of solute-membrane interaction under supersaturated conditions on the transport of model solute (salicylic acid) across poly(dimethylsiloxane) (PDMS) membrane. Supersaturated systems with a degree of saturation (DS) up to 8 were prepared using a molecular form technique with water as the vehicle to minimize the vehicle-membrane interaction. The spectroscopic and thermal analysis revealed the presence of both hydrogen bonding and nonpolar interaction between the solute and PDMS. Upon treatment by supersaturated solutions the degree of solute-membrane interaction increased with increasing DS. This enhanced the barrier property of PDMS and thus led to the flux attenuation compared to that calculated by Higuchi equation. This work highlighted the importance of solute-membrane interaction under supersaturation in the flux reduction, which should be considered when designing, and optimizing supersaturated topical and transdermal drug delivery systems.

Low-density magnetofluid dispersive liquid-liquid microextraction for the fast determination of organochlorine pesticides in water samples by GC-ECD.

A new micro-extraction technique named low-density magnetofluid dispersive liquid-liquid microextraction (LMF-DMMLE) has been developed, which permits a wider range of solvents and can be combined with various detection methods. Comparing with the existing low density solvents micro-extraction methods, no special devices and complicated operations were required during the whole extraction process. Dispersion of the low-density magnetofluid into the aqueous sample is achieved by using vortex mixing, so disperser solvent was unnecessary. The extraction solvent was collected conveniently with an external magnetic field placed outside the extraction container after dispersing. Then, the magnetic nanoparticles were easily removed by adding precipitation reagent under the magnetic field. In order to evaluate the validity of this method, ten organochlorine pesticides (OCPs) were chosen as the analytes. Parameters influencing the extraction efficiency such as extraction solvents, volume of extraction solvents, extraction time, and ionic strength were investigated and optimized. Under the optimized conditions, this method showed high extraction efficiency with low limits of detection of 1.8-8.4 ng L(-1), good linearity in the range of 0.05-10.00 µg L(-1) and the precisions were in the range of 1.3-9.6% (RSD, n=5). Finally, this method was successfully applied in the determination of OCPs in real water samples.

Bioactivity, toxicity and dissipation of hexaconazole enantiomers.

In this study, the bioactivity, acute toxicity and dissipation in vegetables of the individual enantiomers of the fungicide hexaconazole had been investigated. The optical pure single enantiomers were prepared and the bioactivity of (+)-, (-)- and rac-hexaconazole was tested using four target fungi including Colletotrichum gloeosporioides Penz, Alternaria solani, Alternaria mali Roberts and Monilinia fructicola. The results showed (-)-hexaconazole was always more active than (+)-hexaconazole with the fungicidal activity 11­13-fold higher to A. solani, A. mali Roberts and Monilinia fructicola, and 1.26-fold higher to C. gloeosporioides Penz. (-)-Hexaconazole also showed 1.3-fold higher acute toxicity to aquatic species Daphnia magna based on the 48 h EC50 values. There was obvious enantioselectivity in the dissipation in tomato with (-)-hexaconazole degraded faster resulting an enrichment of (+)-form, and the half-lives of (-)-hexaconazole and (+)-hexaconazole in tomato were 2.96 d and 3.38 d respectively, while it was not enantioselective in green pepper, in which the both enantiomers had the half-lives about 4.36 d. The findings are helpful for better environmental and ecological risk assessment of hexaconazole on an enantiomeric level.

Enantioselective behavior of malathion enantiomers in toxicity to beneficial organisms and their dissipation in vegetables and crops.

The dissipation behavior of the two enantiomers of malathion was elucidated in five plant species using enantioselective high performance liquid chromatography (HPLC), and the acute toxicity of the individual enantiomers toward earthworms and honeybees was studied. The calculated LC(50) values of the R-, S- and rac-malathion to earthworms were 0.3869, 25.17, and 19.19 µg/cm(2), respectively, while the calculated LC(50) values of R-, S- and rac-malathion to bees were 2.15, 36.67, and 7.11 µg/mL, respectively. This indicated that the R-enantiomer was more toxic than S-enantiomer. The results of the degradation of racemate in Chinese cabbage and rape showed that the inactive S-(-)-enantiomer degraded faster than the active R-(+)-enantiomer. Inversely, we found a preferential degradation of the R-(+)-enantiomer in sugar beet. However, the degradation of malathion in paddy rice and wheat were nonenantioselectivity. In all plants, malathion was degraded to levels <10% after 5 days, and the calculated t(½) values of the enantiomers ranged from 0.83 to 1.43 days in these five plants. In conclusion, our findings of enantioselectivity in the environmental fate and acute toxicity of the malathion enantiomers may have implications for better environmental and ecological risk assessment for chiral pesticides in general.