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In Australia, trifluralin is one of the commonly used herbicides to manage annual grasses and some broadleaf weeds. However, it may have some ecosystem impacts such as high toxicity to terrestrial and aquatic life, so it is vital to monitor the degradation of trifluralin for a considerable period for environmental safety. For risk assessment purposes, it is necessary to estimate the half-life of trifluralin, which is often evaluated using derived mathematical dissipation models. In the literature, bi-exponential (BEXP) and gamma models were suggested for modelling the dissipation of trifluralin in soil. Both models provide the half-life estimate without discussing the uncertainty of the estimate, which is a shortcoming in the literature. In this paper, we used simulation to illustrate the importance of estimate's uncertainty (standard error) and demonstrated a method to compute the standard error for the half-life estimate mathematically for kinetic dissipation models. Later, we evaluated the performance of the two suggested models using statistical indices. The computation of the half-life and the standard error of the half-life estimate were discussed. This allows us to describe the inference of the half-life parameter and determine whether the half-life estimates are significantly different against the co-variate (moisture) levels. We demonstrated the method to calculate the standard error of the half-life of trifluralin, which allows us to determine the statistical difference between the estimates. In this study, we found that the half-life of trifluralin in soil tends to increase with increasing moisture levels, and the half-life of trifluralin in soil with 100% moisture level is significantly greater than 40% and 70% moisture levels. Our findings suggest that soil moisture levels should be carefully considered before trifluralin application to minimize the non-target environmental damage., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The widespread use of herbicides has increased concern about the hazards and risks to animals living in terrestrial and aquatic ecosystems. A comprehensive understanding of their effective action at different levels of biological organization is critical for establishing guidelines to protect ecosystems and human health. Dinitroanilines are broad-spectrum pre-emergence herbicides currently used for weed control in the conventional agriculture. They are considered extremely safe agrochemicals because they act specifically on tubulin proteins and inhibit shoot and root growth of plants. However, there is a lack of toxicity information regarding the potential risk of exposure to non-target organisms. The aim of the present review is to focus on side effects of the most commonly used active ingredients, e.g. pendimethalin, oryzalin, trifluralin and benfluralin, on animal non-target cells of invertebrates and vertebrates. Acute toxicity varies from slightly to high in terrestrial and aquatic species (i.e. nematodes, earthworms, snails, insects, crustaceans, fish and mammals) depending on the species-specific ability of tested organisms to adsorb and discharge toxicants. Cytotoxicity, genotoxicity and activation of oxidative stress pathways as well as alterations of physiological, metabolic, morphological, developmental and behavioural traits, reviewed here, indicate that exposure to sublethal concentrations of active ingredients poses a clear hazard to animals and humans. Further research is required to evaluate the molecular mechanisms of action of these herbicides in the animal cell and on biological functions at multiple levels, from organisms to communities, including the effects of commercial formulations., (© 2022. The Author(s).)

Trifluralin and acetochlor are two nitrogen-containing current use herbicides. While both herbicides have been observed in the atmosphere and have the potential to undergo atmospheric oxidation before deposition to off-target areas, the atmospheric photooxidation chemistry of these species is poorly understood. We use an oxidative flow reactor to expose the two herbicides to increasing concentrations of OH radicals, detecting pesticides and products using an iodide chemical ionization mass spectrometer. We identify new oxidation products and propose photooxidation mechanisms for trifluralin and acetochlor. Both herbicides contain reduced organic nitrogen atoms, and their OH oxidation produces isocyanic acid. While aerosol was observed in the flow reactor only for acetochlor, our results indicate that OH oxidation of neither herbicide would contribute to secondary organic aerosol formation under typical ambient atmospheric conditions. However, high wall losses of both pesticides in the flow reactor suggests that partitioning to pre-existing aerosol may occur and enable subsequent transport in the atmosphere.

This work reports the potential application of modified gas-diffusion electrode (GDE) with C 60 -CNT composite, as a stable and efficient cathode material for degradation of trifluralin (TRL) pesticide by photo-assisted electrochemical (PE) process. C 60 -CNT composite was prepared and characterized. Subsequently, a novel C 60 -CNT composite modified GDE cathode was developed and the electrochemical and physical characteristics of the modified GDEs were studied. C 60 -CNT composite/GDE showed great efficiencies for electro-generating H 2 O 2 , owing to huge surface area and high conductivity. Afterwards, a comparative study of TRL oxidation via photolysis, anodic oxidation (AO) and PE processes using C 60 -CNT composite/GDE revealed the degradation percentages of 42.2, 48.5 and 93.4%, respectively, after 180 min of treatment. The TRL degradation followed a pseudo-first-order kinetics, being faster in the order: photolysis < AO < PE. The effects of various operational conditions were assessed on the degradation of TRL. From the results, PE process using C 60 -CNT composite/GDE exhibited great performance for the degradation of TRL (20 mg L -1 ) under its original pH, Na 2 SO 4 electrolyte concentration of 0.05 mol L -1 , applied current intensity of 300 mA, and flow rate of 12.5 L h -1 . TOC results displayed that 92.8% of TRL was mineralized after 8 h of PE process. In addition, a plausible pathway for mineralization of TRL was proposed according to the identified by-products detected by means of gas chromatography-mass spectroscopy (GC-MS), High-performance liquid chromatography (HPLC) and ion chromatography analyses., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Fifty years separate the commercialization of the herbicides trifluralin and halauxifen-methyl. Despite the vast degree of technological change that occurred over that time frame, some aspects of their discovery stories are remarkably similar. For example, both herbicides were prepared very early in the iterative discovery process and both were developed from known lead compound structures by hypothesis-driven research efforts without the use of in vitro assays or computer-aided molecular design. However, there are aspects of the halauxifen-methyl and trifluralin discovery stories that are substantially different. For example, the chemical technology required for the cost-effective production of halauxifen-methyl simply did not exist just two decades prior to its commercial launch. By contrast, the chemical technology required for the cost-effective production of trifluralin was reported in the chemical literature more than two decades prior to its commercial launch. In addition, changes in regulatory environment since the early 1960s ensured that their respective discovery to commercial launch stories would also differ in substantial ways. Ultimately, the time and cost required to develop and register halauxifen-methyl demanded a global initial business case while the lower registration hurdles that trifluralin cleared enabled a narrow initial business case mainly focused on the USA. © 2017 Society of Chemical Industry., (© 2017 Society of Chemical Industry.)

Brazil has been the largest world consumer of pesticides since 2008, followed by the USA. The herbicides trifluralin and tebuthiuron have been widely applied in agriculture. These herbicides are selective for some plant species, and their use brings various benefits. However, the genotoxic and mutagenic effects of tebuthiuron on non-target organisms are poorly known, and in addition, the effects of trifluralin must be better investigated. Therefore, this study employed genetic tests including the comet assay and micronucleus test to evaluate the genotoxic effects of trifluralin and tebuthiuron on HepG2 cells. In addition, we have used the Ames test to assess the mutagenic effects of the herbicides on the TA97a, TA98, TA100, and TA1535 strains of Salmonella typhimurium. On the basis of the comet assay and the micronucleus test, trifluralin did not cause genetic damage to HepG2 cells. In addition, trifluralin did not impact the tested S. typhimurium strains. Regarding tebuthiuron, literature has shown that this herbicide damaged DNA in Oreochromis niloticus. Nevertheless, we have found that tebuthiuron was not genotoxic to either HepG2 cells or the S. typhimurium strains. Therefore, neither trifluralin nor tebuthiuron exerted genotoxic or mutagenic potential at the tested conditions.

Herbicides of the dinitroaniline chemical class, widely used oryzalin and trifluralin, and also nitralin were tested as inhibitors of recombinant human carbonic anhydrases (CAs). Oryzalin bound and inhibited 11 out of 12 catalytically active CA isoforms present in the human body with the affinities in the same range as clinically used CA drugs, while no effect was detected for the other two compounds. Binding of all three herbicides was examined by fluorescence-based thermal shift assay, isothermal titration calorimetry, and the inhibition of carbon dioxide hydratase activity. During the last decade, dinitroaniline compound-based therapies against protozoan diseases are being developed. Therefore, it is important to investigate their potential off-target effects, including human CAs., (© 2017 Wiley Periodicals, Inc.)

Dinitroaniline herbicides such as trifluralin and pendimethalin are persistent bioaccumulative toxins to aquatic organisms. Thus, in-situ remediation of contaminated sediments is desired. This study investigated whether black carbons (BCs), including apple wood charcoal (BC1), rice straw biochar (BC2), and activated carbon (BC3), could facilitate abiotic reduction of trifluralin and pendimethalin by sulfides of environmentally-relevant concentrations in anoxic coastal sediments. The reduction rates of trifluralin and pendimethalin increased substantially with increasing BC dosages in the sediments. This enhancing effect was dependent on BC type with the greatest for BC3 followed by BC1 and BC2, which well correlated with their specific surface area. The pseudo-first order reduction rate constants (kobs) for BC3-amended sediment (2%) were 13- and 14 times the rate constants in the BC-free sediment. The reduction rates increased with increasing temperature from 8 to 25°C in the BC-amended sediment, following the Arrhenius relationship. Finally, through molecular modeling by density functional theory and reaction species identification from mass spectra, molecular pathways of trifluralin and pendimethalin reduction were elucidated. In contrary to the separate sequential reduction of each nitro group to amine group, both nitro groups, first reduced to nitroso, then eventually to amine groups., (Copyright © 2016 Elsevier B.V. All rights reserved.)

Over 60% of herbicides are capable of disrupting the endocrine and/or reproductive systems of animals. These herbicides may be released into the atmosphere in both gas and particulate phases, but most of their degradation processes in the atmosphere are not well known. In this study, the heterogeneous reactions of suspended isopropalin, trifluralin, and alachlor particles with NO₃ radicals were investigated using an online vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer. The reaction products for the three herbicides were determined by the assistance of the gas chromatography-mass spectrometer analysis. Mono-dealkylated derivatives were detected as the main reaction products of isopropalin and trifluralin. In addition, an α-amino alcohol product was detected for isopropalin. The carbonylation derivative and the nitro-substituted derivative were the main reaction products observed for alachlor. The reaction mechanism of NO₃ radical-induced N-dealkylation for isopropalin was clarified by density functional theory calculations. It began with the H-abstraction from the N-propyl group, followed by the formation of the α-peroxypropyl radical, α-propyloxy radical, and α-amino alcohol, as well as by the collapse of the α-amino alcohol. The oxidation mechanism for trifluralin is similar to that of isopropalin, whereas the mechanism for alachlor involves carbonylation and nitro-substitution. These results provided insights on the chemical transformation of these herbicides in the atmosphere. The data generated from this study can be used as fundamental information for future studies on their toxic effects to the environment., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Solid-phase microextraction (SPME) was used to determine the equilibrium association constant for a pesticide, trifluralin (TFR), with dissolved organic matter (DOM). After optimization of the SPME method for the analysis of TFR, partition coefficients (K DOM) with three different sources of DOM were determined in buffered solutions at pH 7. Commercial humic acids and DOM fractions isolated from two surface waters were used. The values of log K DOM varied from 4.3 to 5.8, depending on the nature of the organic material. A good correlation was established between log K DOM and DOM properties (as measured with the H/O atomic ratio and UV absorbance), in agreement with literature data. This is consistent with the effect of polarity and aromaticity for governing DOM-pollutant associations, regardless of the origin of DOM. This association phenomenon is relevant to better understand the behavior of pesticides in the environment since it controls part of pesticide leaching and fate in aquatic systems.

In this contribution, we report a new type of Au nanoflower-based nitroaromatic pesticide degradation platform that is fast, efficient, and simple. We found a straightforward, economically viable, and "green" approach for the synthesis and stabilization of relatively monodisperse Au nanoflowers by using nontoxic chemical of hydroxylamine (NH2OH) without stabilizer and the adjustment of the pH environment. This experiment shows that these Au nanoflowers function as effective catalyst for the reduction of pendimethalin in the presence of NaBH4 (otherwise unfeasible if NaBH4 is the only agent employed), which was reflected by the UV/vis spectra of the catalytic reaction kinetics. Importantly, the novel degradation platform could be put in use in two different practical soil samples with satisfactory results under laboratory conditions. To demonstrate the feasibility and universality of our design, two other nitroaromatic pesticides, trifluralin, and p-nitrophenol, were selected and were successfully degraded using this degradation platform.

Pesticide volatilization from bare soil exhibits usually a diurnal cycle with a potentially large decrease when the soil surface dries. We assume here that this decrease may be due to the increase in adsorption of gaseous pesticides to soil under dry conditions. Thus, a precise description of the change with time of water content of the soil surface and of additional process such as gaseous adsorption is required. We used the Volt'Air model: we first extended the van Genuchten curve to drier conditions and then inserted a partitioning coefficient of the pesticide between the air-filled pore space and the soil constituents. This coefficient was calculated by a quantum-chemistry-based method with a dependence on the Specific Surface Area of the soil (SSA) and Relative Humidity (RH) of the air-filled pore space. These developments were assessed by comparing with two data sets on volatilization of trifluralin applied to bare soil. The updated Volt'Air model allowed a better description of the volatilization dynamics on a diurnal cycle (increasing efficiency factor from 0.85 to 0.96 and -2.73 to 0.17 and decreasing RMSE from 146 to 78 and 353 to 168 for both scenarios) as well as the effect of a rewetting situation. Recommendations are made for further refining the description of this process together with the soil water conditions.

The gas-phase degradation of ethalfluralin, N-ethyl-α,α,α-trifluoro-N-(2-methylallyl)-2,6-dinitro-p-toluidine, a widely used herbicide, was investigated under atmospheric conditions at the large outdoor European simulation chamber (EUPHORE) in Valencia, Spain. The photolysis of ethalfluralin was investigated under solar radiation and the mean photolysis rate coefficient was determined: J(ethalfluralin)=(1.3±0.2)×10(-3) s(-1) (JNO2=8×10(-3) s(-1)). The rate coefficients for the reactions of hydroxyl radicals and ozone with ethalfluralin in the dark were also measured under atmospheric conditions using the relative rate and the absolute rate technique, respectively. The rate coefficients values for the reactions of kOH(ethalfluralin)=(3.5±0.9)×10(-11)cm(3)molecule(-1)s(-1), and kO3(ethalfluralin)=(1.6±0.4)×10(-17) cm(3) molecule(-1) s(-1) were determined at 300±5 K and atmospheric pressure. The results show that removal of ethalfluralin from the atmosphere by reactions with OH radicals (τ ~ 4 h) or ozone (τ ~ 25 h) is slow compared to loss by photolysis. The available kinetic data suggest that the gas-phase tropospheric degradation of ethalfluralin will be controlled mainly by photolysis and provide an estimate for the tropospheric lifetime of approximately 12 min. The atmospheric implications of using ethalfluralin as a herbicide are discussed., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Parasitic protozoa of the Leishmania genus cause leishmaniasis, an important complex of tropical diseases that affect about 12 million people around the world. The drugs used to treat leishmaniasis are pentavalent antimonials, miltefosine, amphotericin B and pentamidine. In the present study, we evaluated the effect of a novel alkyl phosphocholine-dinitroaniline hybrid molecule, TC95, against Leishmania amazonensis promastigotes and intracellular amastigotes. Antiproliferative assays indicated that TC95 is a potent inhibitor of promastigotes and intracellular amastigotes with IC50 values of 2.6 and 1.2 μM, respectively. Fluorescence microscopy with anti-α-tubulin antibody revealed changes in the cytoskeleton, whilst scanning electron microscopy showed alterations in the shape, plasma membrane, length of the flagellum, and cell cycle. Flow cytometry confirmed the cell cycle arrest mainly in G1 phase, however a significant population appeared in sub G0/G1 and super-G2. The alterations in the plasma membrane integrity were confirmed by fluorometric analysis using Sytox Blue. Transmission electron microscopy also revealed an accumulation of lipid bodies, confirmed by fluorescence microscopy and fluorometric analysis using Nile Red. Important lesions were also observed in organelles such as mitochondrion, endoplasmic reticulum and Golgi complex. In summary, our study suggests that TC95, an alkyl phosphocholine-trifluralin hybrid molecule, is a promising novel compound against L. amazonensis., (Copyright © 2013 Elsevier Inc. All rights reserved.)

Juvenile Pacific white shrimp (Litopenaeus vannamei) were exposed to trifluralin at 0.1 and 0.01 mg L(-1) for 72 h under controlled conditions. Samples of shrimp and tank water were collected at intervals up to 48 days after exposure. Analysis of the shrimp tissues by gas chromatography-mass spectrometry (GC-MS) and ultrahigh-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UHPLC-qToF-MS) in combination with profiling and metabolite identification software (Agilent MET-ID and Mass Profiler Professional) detected the presence of parent trifluralin together with two main transformation products (TPs), 2-ethyl-7-nitro-5-(trifluoromethyl)benzimidazole (TP1) and 2-amino-6-nitro-4-(trifluoromethyl)phenyl)propylamine (TP2). The highest concentration of trifluralin, determined by GC-MS, was 120 μg kg(-1) at 0 day withdrawal. Residues of trifluralin (CCα = 0.25 μg kg(-1), CCβ = 0.42 μg kg(-1)) were detectable for up to 7 days after exposure. Similarly, the highest concentrations of TP1 and TP 2, determined by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS), were 14 and 18 μg kg(-1), respectively. Residues of TP1 (CCα = 0.05 μg kg(-1), CCβ = 0.09 μg kg(-1)) and TP2 (CCα = 0.1 μg kg(-1), CCβ = 0.17 μg kg(-1)) were detectable for up to 4 and 24 withdrawal days, respectively.

Biochar, a subset of black carbon produced via pyrolysis of biomass, has received much attention in recent years due to its potential to address many important issues, from energy and climate to agriculture and environmental quality. Biochar is known to influence the fate and transport of organic contaminants, although its role has been generally assumed to be as an adsorbent. In this study, the authors investigated the ability of biochar to catalyze the reductive reactions of nitro herbicides and explosives. Two biochars, derived from poultry litter and wastewater biosolids, were found to promote the reductive removal of the dinitro herbicides pendimethalin and trifluralin and the explosives 2,4-dinitrotoluene and hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by dithiothreitol. Parallel experiments using another black carbon material, graphite powder or granular activated carbon, in place of a biochar resulted in comparable rate enhancement to show reduction products, such as 2,4-diaminotoluene and formaldehyde. A cyclization product of trifluralin and reduction products of dinitrotoluene and RDX were detected only when biochar and dithiothreitol were both present, supporting the ability of biochar to promote redox reactions. Three possible catalysts, including graphene moieties, surface functional groups, and redox-active metals, in biochar may be responsible for the biochar-mediated reactions. The environmental significance, implications, and applications of this previously unrecognized role of biochar are discussed., (Copyright © 2013 SETAC.)

Volatilization of pesticides from the bare soil surface is drastically reduced when the soil is under dry conditions (i.e., water content lower than the permanent wilting point). This effect is caused by the hydrated mineral surfaces that become available as additional sorption sites under dry conditions. However, established volatilization models do not explicitly consider the hydrated mineral surfaces as an independent sorption compartment and cannot correctly cover the moisture effect on volatilization. Here we integrated the existing mechanistic understanding of sorption of organic compounds to mineral surfaces and its dependence on the hydration status into a simple volatilization model. The resulting model was tested with reported experimental data for two herbicides from a wind tunnel experiment under various well-defined humidity conditions. The required equilibrium sorption coefficients of triallate and trifluralin to the mineral surfaces, K(min/air), at 60% relative humidity were fitted to experimental data and extrapolated to other humidity conditions. The model captures the general trend of the volatilization in different humidity scenarios. The results reveal that it is essential to have high quality input data for K(min/air), the available specific surface area (SSA), the penetration depth of the applied pesticide solution, and the humidity conditions in the soil. The model approach presented here in combination with an improved description of the humidity conditions under dry conditions can be integrated into existing volatilization models that already work well for humid conditions but still lack the mechanistically based description of the volatilization process under dry conditions.

We evaluated wheat straw biochar produced at 450°C for its ability to influence bioavailability and persistence of two commonly used herbicides (atrazine and trifluralin) with different modes of action (photosynthesis versus root tip mitosis inhibitors) in two contrasting soils. The biochar was added to soils at 0%, 0.5% and 1.0% (w/w) and the herbicides were applied to those soil-biochar mixes at nil, half, full, two times, and four times, the recommended dosage (H(4)). Annual ryegrass (Lolium rigidum) was grown in biochar amended soils for 1 month. Biochar had a positive impact on ryegrass survival rate and above-ground biomass at most of the application rates, and particularly at H(4). Within any given biochar treatment, increasing herbicide application decreased the survival rate and fresh weight of above-ground biomass. Biomass production across the biochar treatment gradient significantly differed (p<0.01) and was more pronounced in the case of atrazine than trifluralin. For example, the dose-response analysis showed that in the presence of 1% biochar in soil, the value of GR(50) (i.e. the dose required to reduce weed biomass by 50%) for atrazine increased by 3.5 times, whereas it increased only by a factor of 1.6 in the case of trifluralin. The combination of the chemical properties and the mode of action governed the extent of biochar-induced reduction in bioavailability of herbicides. The greater biomass of ryegrass in the soil containing the highest biochar (despite having the highest herbicide residues) demonstrates decreased bioavailability of the chemicals caused by the wheat straw biochar. This work clearly demonstrates decreased efficacy of herbicides in biochar amended soils. The role played by herbicide chemistry and mode of action will have major implications in choosing the appropriate application rates for biochar amended soils., (Crown Copyright © 2011. Published by Elsevier Ltd. All rights reserved.)

The oxidation of bromoxynil and trifluralin was investigated using ozone (O(3)) and O(3) combined with hydrogen peroxide (H(2)O(2)) in natural waters using batch reactors. The results indicated that these pesticides could not be completely degraded during ozonation, achieving degradation levels lower than 50%. An enhancement of the level of degradation was observed using O(3)/H(2)O(2) process. A biphasic behaviour of O(3) was also observed. Depending on the experimental conditions, the rate constant for O(3) decomposition was estimated to be between 7.4 × 10(-4) s(-1) to 5.8 × 10(-2) s(-1), and 3.2 × 10(-3) s(-1) to 4.2 × 10(-2) s(-1) for bromoxynil and trifluralin samples, respectively. Acute toxicity analysis performed using Microtox(®) showed a decrease in the toxic effects of the samples on the luminescent bacteria during the first few minutes of treatment, followed by an increase of the toxic effects at the end of the reaction for both pesticides. The quantification of oxidation by-products generated during treatment was also addressed. The total molar balances of the degradation by-products versus the initial pesticide concentrations ranged from 60 to 103% under different experimental conditions., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

The environmental fate of dinitroaniline herbicides is poorly understood, despite their classification as Persistent Bioaccumulative Toxins by the U.S. Environmental Protection Agency. This study investigated the abiotic reduction of pendimethalin and trifluralin in controlled laboratory systems in the presence of Fe(II) and fulvic acids isolated from various surface waters and in sediment pore waters containing naturally abundant levels of dissolved Fe(II) and dissolved organic matter (DOM). It was found that Fe(II) was necessary for pendimethalin and trifluralin reduction to occur in controlled systems and that higher concentrations of DOM slowed Fe(II)-mediated reactions. Pendimethalin and trifluralin reduction in natural pore waters was roughly an order of magnitude slower compared to controlled Fe(II)-DOM solutions, indicating that the reactive Fe(II) species responsible for reduction are concentration-limited in natural pore waters relative to controlled systems. The results show that caution must be exercised when extrapolating results from controlled system reactions to natural systems and that abiotic reduction of both trifluralin and pendimethalin is observed within 3-7 days in anaerobic sedimentary pore waters containing high concentrations of both dissolved Fe(II) and DOM.

The degradation of two pesticides, bromoxynil and trifluralin, was investigated in ultrapure and natural water solutions under ultraviolet (UV) light and a combination of UV and hydrogen peroxide (H(2)O(2)). The effect of pH on the photooxidation of the pesticides was also studied. The results indicated that under direct photolysis with monochromatic light at 253.7 nm and different conditions, the photochemical rates followed first-order kinetics, with fluence-based rate constants ranging from 9.15 x 10(-4) to 6.37 x 10(-3) cm(2) mJ(-1) and 7.63 x 10(-3) to 1.47 x 10(-2) cm(2) mJ(-1) for bromoxynil and trifluralin, respectively. Quantum yields, in the range of 0.08-0.25 for bromoxynil and 0.12-0.72 for trifluralin, were observed in experiments using ultrapure water. The study also found that the UV/H(2)O(2) process enhanced the oxidation rate in comparison to direct photolysis. A 90% degradation with UV dose of 333 and 188 mJ cm(-2) was achieved for bromoxynil and trifluralin, respectively, in natural water, in presence of 8.8 x 10(-4) M H(2)O(2). To assess the aquatic toxicity, the Microtox 81.9% screening test protocol was used before and after treatment. The test results indicated a decrease in the acute toxicity of the samples after treatment for both pesticides., (Copyright (c) 2009 Elsevier Ltd. All rights reserved.)

This study was conducted to assess the effects of solarization and biosolarization on the degradation of oxyfluorfen, ethalfluralin, trifluralin, propyzamide, and pendimethalin. The experimental design consisted of 17 L pots filled with clay-loam soil, which were contaminated with the studied herbicides. Then, soil disinfection treatments were applied during the summer season, including a control without disinfection (C), solarization (S), and biosolarization (BS). Soil from five pots per treatment was sampled periodically up to 90 days. Herbicide dissipation rates were higher in both S and BS treatments with regard to the control. Similar dissipation rates were observed under S and BS for most of the herbicides studied, except oxyfluorfen and pendimethalin, which were degraded to a greater extent in the BS than in the S treatment. The obtained results showed that both solarization and biosolarization can be considered, in addition to soil disinfection techniques, such as bioremediation tools for herbicide-polluted soils.

A series of new analogues of trifluralin (TFL) were synthesized and characterized in view of changing the unfavorable properties that limits its use as antileishmanial agent. Some of the TFL analogues display more activity than a standard drug (miltefosine) against the promastigote forms of Leishmania infantum and Leishmania donovani and the intracellular form (THP-1 infected with L. infantum). All analogues showed a clear advantage over miltefosine, as they are not hemolytic. Some analogues can conjugate these characteristics with reduced cell toxicity and improved intracellular activity., (Copyright (c) 2009 Elsevier Ltd. All rights reserved.)

The ozonation of trifluralin coated on azelaic acid particles is investigated with a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer. The suspended trifluralin particles with the mean diameter of 270nm react with approximately 100ppm ozone in an aerosol reaction chamber under ambient pressure and room temperature (1atm, 298K). The time-of-flight mass spectra of the trifluralin particles and the solid state ozonides are obtained. The assignments of the mass spectra reveal that the major primary ozonides of trifluralin particles are 2,6-dinitro-N-propyl-N-propanoyl-4-(trifluoromethyl) benzamine and 2,6-dinitro-N-(propan-2(and 3)-ol)-N-propyl-4-(trifluoromethyl) benzamine. The major secondary ozonides of trifluralin 2-ethyl-7-nitro-5-(trifluoromethyl) benzimidazole-3-oxide, 2,6-dinitro-N-propyl-4-(trifluoromethyl) benzenamine and 2,6-dinitro-N-(formyl)-N-propyl-4-(trifluoromethyl) benzamine are observed. The primary ozonides are directly resulted from the oxidation of N-propyl groups. The pathways of the primary ozonation are proposed in the paper.

An electroanalytical method has been developed for the determination of the herbicides ethalfluralin[N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl) bezenamine] and methalpropalin [N-(2-methyl-2-propenyl)-2, 6-dinitro-N-propyl-4 (trifluoromethyl) benzenamine] by differential pulse adsorptive stripping voltammetry (DP-AdSV) on a hanging mercury drop electrode (HMDE) with universal buffer as supporting electrolyte. The optimum adsorption conditions were found to be pH 6.0, an accumulation potential of -0.6 V (HMDE vs SCE), an accumulation time of 80 s. and scan rate 45 mVs(-1). Calibration curve is linear in the range 1.30 x 10(-9) to 1.32 x 10(-5) M of ethalfluralin and 1.13 x 10(-5) to 2.0 x 10(-8) M of methalpropalin with detection limits of 1.08 x 10(-9) and 1.87 x 10(-8) M, respectively. The relative SD and correlation coefficients were found to be 1.24%, 0.998 and 1.34%, 0.995, respectively for ten replicates. The method is applied to the determination of the ethalfluralin and methalpropalin in formulations and environmental matrices.

Background: Trifluralin displays anti-Trypanosoma cruzi activity and a potential therapeutic effect for the treatment of Chagas disease. We assessed peroral and intramuscular trifluralin pharmacokinetics in mouse blood and heart tissue., Methods: A parallel experimental design was used. Healthy adult male CF1 albino mice (n = 108, 25-35 g bw) received a single peroral or intramuscular trifluralin dose (50 mg/kg in peanut oil). Blood and heart tissue samples were taken at set times after intramuscular and peroral trifluralin administration. Feces and tissue samples were taken 12 h after intramuscular trifluralin administration. Trifluralin concentrations in whole blood, feces and tissues were determined by HPLC., Results: After intramuscular and peroral administration, maximum whole blood concentration (C(max)) was attained at 30 min and 2.0 h (t(max)) (28.2 +/- 0.7 and 7.8 +/- 0.033 microg/ml; p < 0.05). C(max) in heart tissue was attained at 1.0 and 2.0 h (0.6 +/- 0.004 and 0.2 +/- 0.002 microg/g; p < 0.05). Liver, perirenal and subcutaneous fat concentrations were 55.1, 66.3 and 59.7 ng/mg tissue protein. Peroral and intramuscular penetration ratios determined by comparing heart tissue areas under the curve were 6.3 and 4.0%, respectively., Conclusion: Intramuscular trifluralin could be a new alternative for the treatment of Chagas disease., (Copyright 2009 S. Karger AG, Basel.)

In this study, the genotoxic effects of a widely used herbicide, trifluralin, and its commercial formulation, Treflan, were evaluated using the micronucleus test in a commercially important fish species, Oreochromis niloticus (Nile Tilapia). Fish were exposed to 1, 5, and 10 microg/L doses of trifluralin and Treflan for 3, 6, and 9 days under laboratory conditions. Ethylmethanesulfonate, at a single dose of 10 mg/L, was used as positive control. Micronuclei were evaluated on the peripheral erythrocytes. Both Treflan and trifluralin treatments significantly increased the micronucleus frequencies in peripheral erythrocytes of O. niloticus. Furthermore, the genotoxicity of the active ingredient, trifluralin, was observed to be higher than that of the commercial formulation Treflan. Our results indicate that herbicide trifluralin has genotoxic potential in fish.

Sorption of the herbicides (acetochlor, atrazine, 2,4-D: , chlorotoluron, MCPA and trifluralin) in their commercially available formulations was characterized on six agricultural soils from Slovakia. Weak acid herbicides (2,4-D: and MCPA) were the least sorbed, whereas weak base such as atrazine and nonionic herbicides were the most sorbed in the order: atrazine < acetochlor approximately chlorotoluron < trifluralin, which was closely related to the hydrophobicity of herbicides expressed as logKOW. The KF values positively correlated with soil organic carbon content for all herbicides. Moreover, all herbicides were the most sorbed by Vertisol with relatively high smectite clay content in proportion to organic carbon content. The KOC values for each herbicide showed a smaller variation among soils (excluding Vertisol) than the KF and were used to compare soil mobility potential of herbicides.

Trifluralin is typically applied onto crop residues (trash, stubble) at the soil surface, or onto the bare soil surface after the incorporation of crop residues into the soil. The objective of this study was to quantify the effect of the type and amount of crop residues in soil on trifluralin mineralization in a Wellwood silty clay loam soil. Leaves and stubble of Potato (Solanum tuberosum) (P); Canola (Brassica napus) (C), Wheat (Triticum aestivum) (W), Oats (Avena sativa), (O), and Alfalfa (Medicago sativa) (A) were added to soil microcosms at rates of 2%, 4%, 8% and 16% of the total soil weight (25 g). The type and amount of crop residues in soil had little influence on the trifluralin first-order mineralization rate constant, which ranged from 3.57E-03 day(-1) in soil with 16% A to 2.89E-02 day(-1) in soil with 8% W. The cumulative trifluralin mineralization at 113 days ranged from 1.15% in soil with 16% P to 3.21% in soil with 4% C, again demonstrating that the observed differences across the treatments are not of agronomic or environmental importance.

A method for the simultaneous determination of 9 pesticides (dinitroanilines, organophosphorus, triazoles, and pyrimidines) in several products (malt, spent grains, wort, and beer) of the beer industry is reported. Solid samples (malt and spent grains) are extracted by homogenization with a water-hexane mixture, and the pesticides are partitioned with dichloromethane. Liquid samples (wort and beer) are extracted by sonication with a hexane-dichloromethane mixture. Determination of pesticide residues was made by capillary gas chromatography with an electron capture detector (ECD). Confirmation of the compounds was performed by gas chromatography/ion trap mass spectrometry in the selected ion monitoring mode. Detection limits for GC-ECD varied from 0.2 to 5.5 pg for trifluralin and malathion, respectively. Recoveries of the pesticides from spiked samples ranged from 81.2 to 113.7% with a relative standard deviation between 3.4-7.5%. The method presents good linearity over the studied range (0.005-2 microg/mL). The proposed method is rapid and reliable and can be useful for routine monitoring during brewing.

The gas phase atmospheric degradation of trifluralin (a widely used herbicide) has been investigated at the EUPHORE facility. Its photolysis has been studied under sunlight conditions and its reaction rate constant with HO() radicals was measured using the relative rate method. Using 1,3,5-trimethylbenzene as reference compound, the rate constant of HO() reaction with trifluralin was obtained to be [formula: see text] The mean photolysis rate measured under solar radiation was [formula: see text] . The photolysis of trifluralin was found to generate organic aerosols with a yield of (20 +/-10)%. The data obtained enabled us to discuss the atmospheric fate of trifluralin in the gas phase.

A multi-pesticide (MP) method was developed and single-laboratory validated for the quality control of commercial pesticide products containing alachlor, chlorpyrifos methyl, fenthion and trifluralin as active ingredients (a.i.). A capillary gas chromatographic system with flame ionization detection (FID) and a programmable temperature vaporising split injector was used. The performance characteristics (specificity, linearity, precision and repeatability) of the method satisfied international acceptability criteria.

Despite years of use as commercial herbicides, it is still unclear how dinitroanilines interact with tubulin, how they cause microtubule disassembly, and why they are selectively active against plant and protozoan tubulin. In this work, through a series of computational studies, a common binding site of oryzalin, trifluralin, and GB-II-5 on apicomplexan and kinetoplastid alpha-tubulin is proposed. Furthermore, to investigate how dinitroanilines affect tubulin dynamics, molecular dynamics simulations of Leishmania alpha-tubulin with and without a bound dinitroaniline are performed. The results obtained provide insight into the molecular mechanism by which these compounds interact with tubulin and function to prevent microtubule assembly. Finally, to aid in the design of effective parasitic microtubule inhibitors, several novel dinitroaniline analogues are evaluated. The location of the binding site and the relative binding affinities of the dinitroanilines all agree well with experimental data.

Over the past decade, electron monochromator-mass spectrometry (EM-MS) has been shown to be a selective and sensitive technique for the analysis of a wide variety of electrophilic compounds in complex matrixes. Here, for the first time, three different dinitroaniline pesticides, flumetralin, pendimethalin, and trifluralin, have been shown to be present in both mainstream and sidestream tobacco smoke using an EM-MS system. A number of cigarettes were tested that included three pure-tobacco-type cigarettes, an experimental reference cigarette, and 11 commercial cigarettes. Due to the complexity of the smoke particulate matter, the pesticides were identified only after each sample was subjected to a multistep cleanup process that included phenyl solid-phase extraction; an acid wash; aminopropyl solid-phase extraction; and finally, normal phase LC fractionation. All cigarette types tested showed the presence of the three pesticides in the tobacco smoke, with flumetralin ranging from trace levels up to 37 (+/- 9) ng/cig, pendimethalin ranging from trace levels up to 10.4 (+/- 0.6) ng/cig, and trifluralin ranging from trace levels up to 47 (+/- 17) ng/cig. Acute toxicity information is presented for the three pesticides.

Microtubules play important roles in cell division, motility and structural integrity of malarial parasites. Some microtubule inhibitors disrupt parasite development at very low concentrations, but most of them also kill mammalian cells. However, the dinitroaniline family of herbicides, which bind specifically to plant tubulin, have inhibitory activity on plant cells but are relatively non-toxic to human cells. Certain dinitroanilines are also inhibitory to various protozoal parasites including Plasmodium. Here we demonstrate that the dinitroanilines trifluralin and oryzalin inhibited progression of erythrocytic Plasmodium falciparum through schizogony, blocked mitotic division, and caused accumulation of abnormal microtubular structures. Moreover, radiolabelled trifluralin interacted with purified, recombinant parasite tubulins but to a much lesser extent with bovine tubulins. The phosphorothioamidate herbicide amiprophos-methyl, which has the same herbicidal mechanism as dinitroanilines, also had antimalarial activity and a similar action on schizogony. These data suggest that P. falciparum tubulin contains a dinitroaniline/phosphorothioamidate-binding site that is not conserved in humans and might be a target for new antimalarial drugs.

The treatment of an effluent from the production of trifluraline was studied using a 1-L, semi-batch, tank-stirred glass reactor for performing three different advanced oxidation processes (photoperoxidation, Fenton, photo-Fenton). A commercial, medium-pressure mercury lamp was used for sample irradiation. The degradation was monitored by measurements of absorptiometric color reduction, UV-visible absorption spectra, and chemical oxygen demand (COD). The obtained results showed that the photo-Fenton process was the most effective treatment for the trifluraline effluent.

The kinetics of direct photochemical transformations of organic compounds in light absorbing and scattering media has been sparsely investigated. This is mostly due to the experimental difficulties to assess the major parameters: light intensity in porous media, the reaction quantum yield and the molar absorption coefficient of the adsorbed compound, epsilon(i) (lambda). Here, we propose a method for the determination of the molar absorption coefficient of compounds adsorbed to air-dry surfaces using the Kubelka-Munk model for the description of radiative transfer. To illustrate the method, the molar absorption coefficients of three compounds, i.e. 4-nitroanisole (PNA), the herbicide trifluralin and the flame retardant decabromodiphenyl ether (DecaBDE), were determined on air-dry kaolinite. The measured diffuse reflectance spectra were evaluated with the Kubelka-Munk model and with previously determined Kubelka-Munk absorption and scattering coefficients (k and s), for kaolinite. For all compounds the maximum absorption band was found to be red shifted and the corresponding epsilon(i) (lambda) values were significantly greater than those determined in solvents. Together with the absorption and scattering coefficient of the medium, the measured epsilon(i) (lambda) can be used to determine the quantum yield of the photochemical reaction in this medium from experimentally determined reaction kinetics.

Use of glyphosate resistant crops was helpful in addressing observed increases in environmental contamination by herbicides. Glyphosate is a broad-spectrum herbicide, and its behaviour-as well as that of other herbicides-in soils is an important consideration for the overall environmental evaluation of genetically resistant crop introduction. However, few data have been published comparing glyphosate behaviour in soil to that of the herbicides that would be replaced by introduction of glyphosate resistant crops. This work compares glyphosate adsorption in soil with that of other herbicides frequently used in rape (trifluralin and metazachlor), sugarbeet (metamitron) and corn (sulcotrione). Herbicide adsorption was characterised in surface soils and in the complete soils profiles through kinetics and isotherms using batch equilibration methods. Pedological and molecular structure factors controlling the adsorption of all five herbicides were investigated. Glyphosate was the most strongly adsorbed herbicide, thus having the weakest potential for mobility in soils. Glyphosate adsorption was dependent on its ionisable structure in relation to soil pH, and on soil copper, amorphous iron and phosphate content. Trifluralin adsorption was almost equivalent to glyphosate adsorption, whereas metazachlor, metamitron and sulcotrione adsorption were lower. Trifluralin, metazachlor and metamitron adsorption increased with soil organic carbon content. Sulcotrione was the least adsorbed herbicide in alkaline soils, but its adsorption increased when pH decreased. Ranking the adsorption properties among the five herbicides, glyphosate and trifluralin have the lowest availability and mobility in soils, but the former has the broadest spectrum for weed control.

Batch adsorption and desorption experiments were performed using thirteen agricultural soil samples and five pesticides. Experimental data indicated a gradient in pesticide adsorption on soil: trifluralin >> 2,4-D > isoproturon> atrazine >> bentazone. Atrazine, isoproturon and trifluralin adsorption were correlated to soil organic matter content (r2 = 0.7, 0.82, 0.79 respectively). Conversely, bentazone adsorption was governed by soil pH (r2 = 0.68) while insignificant effect has been shown in the case of 2,4-D. Multiple linear regressions were used to combine relationships between the various soil parameters and the Freundlich adsorption coefficient (K(f)) of each pesticide. Then desorption was assessed since it may reflect some of the interactions involved between the pesticides and the soil components. Adsorbed molecules were released into aqueous solution in the following order: bentazone >> atrazine> isoproturon> 2,4-D >> trifluralin. The occurrence of hysteresis did not allow an accurate interpretation of the pesticide desorption data because of the possible interplay of several processes.

The herbicide trifluralin (I)(N,N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline) decomposes, by the action of UV-Vis light (lambda > 300 nm), to several products, the most important (because they give subsequent photochemical reactions) being N-n-propyl-2,6-dinitro-4-trifluoromethylaniline (VI), 2-ethyl-7-nitro-5-trifluoromethyl-1H-benzimidazole 3-oxide (VII) and 2,6-dinitro-4-trifluoromethylaniline (XII). The time evolution of degradation of trifluralin (I) and the aforementioned three main photoproducts was studied in water and acetonitrile as solvents. The pseudo-first order rate constants allow one to calculate the branching ratios for some of the reactions involved. The preference for either N-dealkylation or cyclization depends on the solvent employed. Dissolved oxygen accelerates the photodegradation, especially the dealkylation.

Desorption kinetics were determined for fluoranthene (FLU) and trifluralin (TF) spiked onto Lake Erie and Lake Huron, USA, sediments at three concentrations (10, 40, 100 mg/kg dry wt). Following four months of equilibration, desorption was measured by extraction with Tenax and the data were fit to a first-order three-compartment kinetic model. The rate constants of the rapidly (k(rap)), slowly (k(slow)), and very slowly (k(vs)) desorbing fractions were on the order of 10(-1)/h, 10(-2-3)/h, and 10(-4)/h, respectively. The t99.9 (time required for 99.9% of the FLU and TF to desorb from each pool value) for each compartment indicated that FLU and TF desorption from rapid, slow, and very slow compartments were on the order of hours, days, and years, respectively. Higher rates of desorption were observed for FLU and TF from the Lake Huron sediments and this was not apparently related to the total organic carbon (TOC), particle size distribution, or polarity (carbon-to-nitrogen ratio) of the sediments. In general, the total fraction of the initial contaminant amounts that desorbed over the time course was directly related to concentration, which we hypothesized was due to the combined effects of saturation of high-energy (slow and very slow) binding sites in the organic carbon matrix and hysteresis. In extrapolations to field conditions, FLU and TF were predicted to persist in the sediments for years due to the very slow desorption of an estimated 31 to 53% of the bulk concentrations. Based on the rapidly desorbing fractions, the bioavailable amounts of the contaminants were predicted to be between 31 to 55% of bulk sediment concentrations.

Six major use pesticides (Atrazine, Dicamba, Isoproturon, Lindane, Paraquat and Trifluralin) with differing physico-chemical properties were evaluated for the significance of 'bound' or non extractable residue formation. Investigations were carried out in purpose-built microcosms where mineralization, volatilisation, 'soil water' extractable and organic solvent extractable residues could be quantified. Extractable residues were defined as those accessible by sequential extraction where the solvent used became increasingly non-polar. Dichloromethane was the 'harshest' solvent used at the end of the sequential extraction procedure. (14)C-labelled volatilised and (14)CO(2) fractions were trapped on exit from the microcosm. The pesticides were categorised into 3 classes based on their behaviour. (i) Type A (Atrazine, Lindane and Trifluralin) in which ring degradation was limited as was the formation of non-extractable residues; the remainder of the (14)C-activity was found in the extractable fraction. (ii) Type B (Dicamba and Isoproturon) in which approximately 25% of the (14)C-activity was mineralised and a large portion was found in the non-extractable fraction after 91 days. Finally, Type C (Paraquat) in which almost all of the (14)C-activity was quickly incorporated into the non-extractable fraction. The implications of the data are discussed, with respect to the variability and significance of regulatory aspects of non-extractable residues.

Isoproturon and trifluralin are herbicides of contrasting chemical characters and modes of action. Standard batch sorption procedures were carried out to investigate the individual sorption behaviour of 14C-isoproturon and 14C-trifluralin in five agricultural soils (1.8-4.2% OC), and the soil solid-liquid partition coefficients (Kd values) were determined. Trifluralin exhibited strong partitioning to the soil solid phase (Kd range 106-294) and low desorption potential, thus should not pose a threat to sensitive waters via leaching, although particle erosion and preferential flow pathways may facilitate transport. For isoproturon, soil adsorption was low (Kd range 1.96-5.75) and desorption was high, suggesting a high leaching potential, consistent with isoproturon being the most frequently found pesticide in UK surface waters. Soil partitioning was directly related to soil organic carbon (OC) content. Accumulation isotherms were modelled using a dual-phase adsorption model to estimate adsorption and desorption rate coefficients. Associations between herbicides and soil humic substances were also shown using gel filtration chromatography.

Column studies were conducted to determine the ability of ozone to degrade aniline and trifluralin in soil. Ozone rapidly degraded aniline from soil under moist soil conditions, 5% (wt). Removal of 77-98% of [UL-14C]-aniline was observed from soil columns (15 ml, i.d. = 2.5 cm), exposed to 0.6% O(3) (wt) at 200 ml/min after 4 min. Initial ozonation products included nitrosobenzene and nitrobenzene, while further oxidation led to CO(2). Ring-labeled-[UL-14C]-trifluralin removal rates were slower, requiring 30 min to achieve removals of 70-97%. Oxidation and cleavage of the N-propyl groups of trifluralin was observed, affording 2,6-dinitro-4-(trifluoromethyl)-aniline, 2,6-dinitro-N-propyl-4-(trifluoromethyl)-benzamine, and 2,6-dinitro-N-propyl-N-acetonyl-4-(trifluoromethyl)-benzamine. Base solutions revealed that trifluralin was similarly oxidized to CO(2), where 72-83% of the activity recovered comprised 14CO(2). Use of ozone-rich water improved contaminant removal in trifluralin-amended soil columns, but did not improve removal in aniline, pentachloroaniline, hexachlorobenzene amended soil columns, suggesting that ozonated water may improve contaminant removal for reactive contaminants of low solubility., (Copyright 2002 Elsevier Science Ltd.)

Trifluralin[2,6-dinitro-N,N-dipropyl-4-(trifluormethyl)benzenamine], metolachlor[2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide], and metribuzin[4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)one] were applied in field plots located on a Commerce clay loam soil near Baton Rouge, Louisiana at the rate of 1683 g/ha, 2759 g/ha and 609 g/ha, respectively. The half-lives of trifluralin, metolachlor, and metribuzin in the top 0-15 cm soil depth were found to be 54.7 days, 35.8 days and 29.8 days, respectively. The proportion of trifluralin, metolachlor, and metribuzin in the top 0-15 cm soil depth was 94.7%, 86.6%, and 75.4%, respectively of that found in the top 0-60 cm soil depth 30 days after application. Trifluralin concentrations were within a range of 0.026 ng/mL to 0.058 ng/mL in 1 m deep well water, and between 0.007 ng/mL and 0.039 ng/mL in 2 m deep well water over a 62 day period after application. Metolachlor concentrations in the 1 m and 2 m wells ranged from 3.62 ng/mL to 82.32 ng/mL and 8.44 ng/mL to 15.53 ng/mL, respectively. Whereas metribuzin concentrations in the 1 m and 2 m wells ranged from 0.70 ng/mL to 27.75 ng/mL and 1.71 ng/mL to 3.83 ng/mL, respectively. Accordingly, trifluralin was found to be strongly adsorbed on the soil and showed negligible leaching. Although metolachlor and metribuzin were also both readily adsorbed on the soil, their leaching potential was high. As a result, in the clay loam soil studied, metribuzin concentration in groundwater with shallow aquifers is likely to exceed the 10 mg/L US Environmental Protection Agency (EPA) advisory level for drinking water early in the application season, whereas trifluralin and metolachlor concentrations are expected to remain substantially lower than their respective 2 ng/mL and 175 ng/mL EPA advisory levels.

The dissipation rate of seven currently used soybean and corn pesticides in two tropical soils (Ustox and Psamments) of Brazil was studied in a laboratory incubation experiment. Dissipation half-lives of pesticides ranged between 2 (monocrotofos) and 90 days (endosulfan-beta). The contrasting clay contents of the studied tropical soils (130 versus 470 g of clay kg(-1) of soil) did not influence the dissipation dynamics of pesticides substantially. Mineralization to CO(2) was high [up to 78% of the applied radioactivity (AR)] for the studied organophosphorus compounds and deltamethrin, which also formed considerable amounts of bound residues (>20% of AR) during the 80 days of incubation. The highest portion of nonextractable residues was found for alachlor and simazine (55-60% of AR). In contrast, the nonpolar trifluralin and endosulfan formed only small amounts of bound residues (mostly <20% of AR) but showed the highest dissipation half-lives (>14 days) in the studied soils, also due to a low mineralization rate. When endosulfan-sulfate, as the main metabolite of endosulfan, was considered, the half-life time of endosulfan compounds (sum of -alpha, -beta, and -sulfate) was enhanced to >160 days in both soils. In comparison with the laboratory experiments, dissipation half-life times of chlorpyrifos, endosulfan-alpha, and trifluralin were shortened by a factor of 10-30 in field trials with the same soils, which was related to the volatilization potential of pesticides from soils.

The volatile and soil loss profiles of six agricultural pesticides were measured for 20 days following treatment to freshly tilled soil at the Beltsville Agricultural Research Center. The volatile fluxes were determined using the Theoretical Profile Shape (TPS) method. Polyurethane foam plugs were used to collect the gas-phase levels of the pesticides at the TPS-defined critical height above a treated field. Surface-soil (0-8 cm) samples were collected on each day of air sampling. The order of the volatile flux losses was trifluralin > alpha-endosulfan > chlorpyrifos > metolachlor > atrazine > beta-endosulfan. The magnitude of the losses ranged from 14.1% of nominal applied amounts of trifluralin to 2.5% of beta-endosulfan. The daily loss profiles were typical of those observed by others for volatile flux of pesticides from moist soil. Even though heavy rains occurred from the first to third day after treatment, the majority of the losses took place within 4 days of treatment, that is, 59% of the total applied atrazine and metolachlor and >78% of the other pesticides. Soil losses generally followed pseudo-first-order kinetics; however, leaching due to heavy rainfall caused significant errors in these results. The portion of soil losses that were accounted for by the volatile fluxes was ordered as follows: alpha-endosulfan, 34.5%; trifluralin, 26.5%; chlorpyrifos, 23.3%; beta-endosulfan, 14.5%; metolachlor, 12.4%; and atrazine, 7.5%.

The drugs presently in use against Chagas disease are very toxic, inducing a great number of side effects. Alternative treatments are necessary, not only for Chagas disease but also for other diseases caused by protozoan parasites where current drugs pose toxicity problems. The plant microtubule inhibitor trifluralin has previously been tested with success against Leishmania, Trypanosoma brucei and several other protozoan parasites. Trypanosoma cruzi, the causative agent of Chagas disease, is also sensitive to the drug. This sensitivity has been correlated with the deduced amino acid sequences of alpha- and beta-tubulin of T. cruzi as compared with plant, mammal and other parasite sequences.