The current study assessed the bioavailability of slower desorbing sediment-associated permethrin by manipulating the desorption properties of two sediments with an absorbent, Amberlite XAD-4. The two sediments differed in OC content and the size of the rapidly desorbing pool and rate constants were smaller in the higher OC sediment. Manipulation decreased desorption rate constants in the treated sediments compared to the untreated sediments. Greater activity of permethrin in the pore water was observed in the lower OC sediment compared to the higher OC sediment, and in the untreated sediment compared to the treated sediment. The higher occurrence of permethrin in the pore water was attributable to the larger pool of rapidly desorbing compound. Based on BAF calculations, bioaccumulation of permethrin by all three species was lower in the higher OC sediment compared to the lower OC sediment, and bioaccumulation was also lower in the treated sediments compared to the untreated sediments for Lumbriculus variegatus and Hexagenia sp., suggesting that bioavailability was reduced for those organisms. Desorption rate constants suggest that a reduction in desorption was the cause. However, bioaccumulation was not reduced for Hyalella azteca whose body residues were not significantly different between the two treatments and so BAF values did not reflect a reduction in bioavailability. The results for H. azteca do not match with typical observations, where bioaccumulation decreases with decreased desorption; suggesting that an important exposure pathway for those organisms was not influenced heavily by the sediment desorption properties. Therefore, the role of ingestion was investigated as a route of uptake. Synthetic digestive fluid extractions increased desorption compared to water; indicating that ingestion increased desorption, and thus bioavailability of sediment-associated permethrin. Estimated pore water and feeding contributions suggested that more than one route of exposure contributed to the uptake of permethrin, and that neither exposure route was responsible for uptake alone. The contribution from feeding was estimated to be greater than the contribution from pore water for WBS sediment for all three species, and for the treated sediments compared to the untreated sediments; indicating that as desorption decreases, the role of ingestion in uptake increases. Therefore, pore water may be more important to the contribution of uptake for faster desorbing compound, and ingestion may be more important to the contribution of uptake for slower desorbing compound.

No description available.

No description available.

Altered immune responses have been observed following occupational, inadvertent, or therapeutic exposure to xenobiotics. Many pesticides are known to cause immunotoxicity. Exposure to mixtures of pesticides, either concurrently or sequentially, may result in potentiating this effect partly because one can effect the metabolism of the other. The objective of this study was to determine the effect of the insecticides endosulfan, permethrin and their mixtures on C57/BL6 male mice thymocytes in vitro and to ascertain the mechanism by which these effects take place. Permethrin, a broad-spectrum synthetic pyrethroid, is a widely used insecticide in agriculture and public health. Endosulfan is a highly toxic chlorinated hydrocarbon insecticide used worldwide. We examined the immunotoxic potential of these pesticides using a flow cytometric technique in combination with 7-Amino Actinomycin D (7AAD) to distinguish live, early apoptotic, and late apoptotic/necrotic cells. DNA ladder assay, a hallmark of apoptosis, was also used to determine the occurrence of apoptosis. Both endosulfan and permethrin were found to cause significant apoptotic death of thymocytes in a dose- and time- dependent manner. Thus, permethrin at 50, 100 or 300 µM was found to cause 5.5, 11.5 and 26.1% increases in early apoptotic cell death relative to control, respectively. Endosulfan at 25, 50 or 250 µM was found to cause 11.9, 15.7 and 68.0% early apoptotic cell death, respectively. For the mixture study, concentrations of 100 µM permethrin and 50 µM endosulfan were selected and found to cause 27.1% apoptosis. Thus, these pesticides in mixture have an additive immunotoxic effect. Increases in late-apoptotic/necrotic cells were found at these concentrations for either pesticide when exposed for 12 hours. DNA ladder assay confirmed the presence of DNA fragments and therefore the presence of significant apoptotic cell death. Apoptosis is a morphologically distinct form of cell death that can be mediated by a variety of pathological and physiological stimuli. Because permethrin and endosulfan were found to induce apoptosis in C57/BL6 mice thymocytes in vitro, the objective of the second half of this study was to elucidate the potential mechanism by which these pesticides regulate apoptosis in immune cells. Caspases are a family of cystine-dependent, aspartate-directed proteases that have an integral role in apoptotic cell death. Caspases, which are normally inactive in healthy cells, are activated during apoptosis and form an irreversible cascade. There are two subsets of caspases, initiator caspases (i.e. caspase 8 and 9) and effector caspases (i.e. caspases 3 and 6). Caspase 3, a downstream effector of apoptosis, is activated by many different pathways and is an apoptotic marker in cells. Caspase 8 is the apical caspase in the extrinsic pathway. Caspase 9 is the apical caspase in the intrinsic pathway, therefore we investigated mechanisms of pesticide induced apoptosis involving the thymocyte caspase system. Thymocytes from C57/BL6 mice were incubated with varying concentrations of pesticides for varying amounts of time. Active caspase 3 was then measured using EnzCheck Caspase 3 Assay Kit. Relative fluorescence for permethrin exposed cells after 12 hours incubation in the presence of pesticides at 150, 100, and 50 µM and 40 minutes in the presence of AFC-substrate was found to be 387, 386, and 297, respectively. Relative fluorescence for endosulfan exposed cells at 150, 100 and 50 µM was 188, 177, and 294. Caspase 3 activity increased as permethrin concentrations increased and decreased as endosulfan concentrations were increased. Then the extrinsic and intrinsic pathways of apoptosis were further investigated. Active caspase 8 was measured using the ApoAlert Caspase Fluorescent Assay Kit. Relative fluorescence for permethrin exposed cells after 7 hours incubation in the presence of pesticides at 100, 150, and 200 µM was found to be 35.5, 10.5, and 0, respectively. Relative fluorescence for endosulfan exposed cells after 7 hours incubation at 25, 50, 100 and 150 µM was found to be 32.8, 63.8, 69.5, and 55.5, respectively. A mixture study was then performed using endosulfan (50, 100, 150 µM) combined with permethrin (100 µM). All combinations were found to have more than an additive effect, therefore the extrinsic pathway seems to be involved. Caspase 9 activity was measured using Caspase 9/Mch6 Fluorometric Protease Assay Kit. Relative fluorescence for endosulfan exposed cells after 7 hours incubation at 25, 50, 100 and 150 µM was found to be 43, 73, 78.9, and 5.12, respectively. Relative Fluorescence for permethrin exposed cells at 100, 150 and 200 µM was found to be 34.5, 39, and 55.5, respectively. A mixture study was then performed using endosulfan (25, 50 µM) combined with permethrin (100 µM). Both combinations were found to have less than an additive effect. These results suggest that apoptosis caused by both endosulfan and permethrin exert their effects via the caspase pathway. The results also show that mixtures of pesticides have a less than additive effect on caspase 9 activation and more than an additive effect on caspase 8 activation, therefore the extrinsic pathway is predominantly involved in thymocyte apoptosis caused by mixtures of permethrin and endosulfan. / Master of Science

The traditional approach for predicting the risk of hydrophobic organic contaminants in sediment is to relate organic carbon normalized sediment concentrations to body residues or toxic effects in organisms. This method is limited, however due to the plethora of variables that can influence bioavailability. Therefore, a matrix independent method of predicting bioavailability needs to be developed in order to be universally applicable. Solid phase microextraction (SPME) and Tenax are two commonly used bioavailability-based methods. While both SPME fiber and Tenax extractable concentrations can be correlated to tissue residues of aquatic species, the majority of this research (with a few exceptions) focuses on compounds that are not acutely toxic or biotransformed. Less is known about the potential applicability of these methods to predict bioaccumulation, and ultimately toxicity, for highly toxic, rapidly biotransformed compounds, such as pyrethroid insecticides. This class of compounds is of particular concern due to frequent environmental detection in sediments at concentrations lethal to benthic species. This research has four specific goals: Determining exposure conditions that may change the concentration on the SPME fibers at equilibrium (Chapter 2); Comparing the ability of SPME fibers and Tenax to predict the bioavailability of two pyrethroids (permethrin and bifenthrin) (Chapter 3); Developing bioavailability-based toxicity endpoints for bifenthrin using two aquatic species (Chapter 4); and, Validating these techniques using sediments from known contaminated field sites (Chapter 5). Overall this research was focused on comparing and contrasting the ability and applicability of SPME fibers and Tenax to adequately predict the exposure of pyrethroids under varying conditions. While comparing these two methods, they were optimized to better provide accurate predictions of bioavailability and toxicity for pyrethroids from sediments. Regardless of the fiber or animal density examined, the SPME fibers exposure did not significantly affect fiber concentrations for permethrin or DDE. Additionally, bioaccumulation of parent permethrin and bifenthrin was predicted using both SPME fibers and Tenax using 6 or 24 h extraction times. Further, a single regression model predicted bioaccumulation across compounds and species using Tenax extractable concentrations. Once demonstrated that these techniques could predict bioaccumulation, median lethal and effect levels were examined for bifenthrin and as expected the bioavailability-based endpoints were more uniform across sediments than use of whole sediment concentrations. Additionally, the relationships among the two methods were compared across multiple sediments. Despite the SPME fiber's ability to determine toxicity in laboratory sediments, the field validation study determined that lethal levels were often too low to detect on the SPME fibers using current methodologies, but Tenax extractable concentrations correlated to toxicity. Overall, while both methods could predict bioavailability, the limitations of SPME fibers including lower sensitivity, inability to function across compounds, and long equilibration time, made Tenax extraction a preferable method.

Previous monitoring studies by federal agencies such as the United States Geological Survey have shown that environmental contaminants rarely occur as single compounds but, rather, as mixtures. In aquatic ecosystems, mixtures of these compounds are often complex, sometimes containing dozens of compounds across a number of different chemical classes. Non-target aquatic organisms are frequently exposed to varying levels of contaminants based upon the physical properties of the chemicals, such as water solubility, and life-cycle habits of the individual organisms. In addition to this, past research has indicated that the presence of one class of contaminant may have an influence on the toxicities of other chemical classes. Water-only toxicity testing has historically provided a means by which researchers can rapidly determine the toxic effects of water-soluble compounds such as triazine herbicides and organophosphate insecticides. However, many legacy pesticides, such as organochlorine, and some current-use pesticides, such as pyrethroids, are strongly hydrophobic, and suspended or bedded sediments, rather than water, would generally be more appropriate matrices for monitoring. Yet sampling of sediments and quantification of residues of these pesticides is often lacking. Similarly, there have been few studies examining the toxicity of mixtures of these compounds in sediment. The first goal of this research was to examine the effects of select triazine herbicides on organophosphate insecticide toxicity utilizing water-only toxicity test with the aquatic amphipod Hyalella azteca. The second goal was to analyze an existing database of chemical concentrations using a toxicity-based screening approach in order to estimate the environmental hazard posed by mixtures of pyrethroid, organochlorine, and organophosphate insecticides in sediment to H. azteca. The third goal of this research was to examine the toxic effects of mixtures of different pyrethroid insecticides to H. azteca using compounds identified as most relevant from the screening phase of the study. The fourth goal of this research was to examine how pyrethroid and organochlorine insecticides partition between different size fractions within sediment and detritus, as well as between sediments with differing organic carbon content, and the resulting effects to compound toxicity and bioavailability. The final goal of this research was to examine potential modifications to bifenthrin sediment partitioning, toxicity, and bioaccessibility resulting from various dissolved salt concentrations in overlying water using H. azteca and Chironomus dilutus as reference organisms. Together, the individual objectives of this study provide a thorough and multi-tiered approach to determining the occurrence, environmental fate, biological effects, and bioavailability of frequently detected and co-occurring environmental contaminants in both agricultural and urban landscapes.

A new synthetic route to natural and novel pyrethroid acids was developed utilizing ketene cycloaddition which is a significant improvement over existing syntheses. The newly synthesized pyrethroid acids were converted to pyrethroid esters and used to study structure-activity relationships. The cycloaddition of dichloroketene with 2,5-dimethyl-2,4-hexadiene yields (2+2) cycloaddition products, 2,2-dichlorocyclobutanones. The reductive removal of one chlorine atom from these cycloaddition products gave monochlorocyclobutanones which underwent a Favorskii-type ring contraction to yield cis- and trans-chrysanthemic acids. 4-Methyl-1,3-pentadiene was also used as a precursor in this synthetic scheme to yield an analogue of the chrysanthemic acid. These results are consistent with a concerted cycloaddition process involving a dipolar transition state. The zinc reduction is not a regiospecific reaction which accounts for the two regioisomers of the monochlorocyclobutanones. The Favorskii-type ring contraction is a regiospecific reaction. A variety of different bicyclo(3.1.0)alkenecarboxylates and bicyclo(4.1.0)heptenecarboxylates were synthesized from alkylcyclopentadiene and fulvene derivatives. These new bicyclo pyrethroid acids are structurally similar to the natural chrysanthemic acid but are rigid and locked in a single conformation which is likely the least stable conformer of the natural acid. The acids were converted to pyrethroid esters and tested against the housefly and cockroach. The test results indicate that the bicyclo pyrethroids synthesized are not as active as the natural pyrethroid. Apparently, these bicyclo pyrethroids with structures similar to the less stable conformer of the natural pyrethroids are of little consequence as it binds to the target site in the insect. In an effort to learn more about the conformational requirements of the pyrethroid acid, a new bicyclo-spiro pyrethroid system with a structure similar to the most stable conformation of the natural pyrethroid was designed and synthesized. These bicyclo-spiro pyrethroids were derived from a new isopropylidenecyclobutane derivatives as a starting compound instead of a conjugated diene. The test results of these bicyclo-spiro pyrethroid esters revealed a much greater activity against the housefly and cockroach. This study establishes that the more stable conformer of the natural pyrethroid acid provides a much higher toxicity against the insects tested.

Desde a revolução verde, na década de 1950, o processo tradicional de produção agrícola passou por mudanças com a inserção do uso intensivo de agrotóxicos como os piretróides, que são a terceira classe química de pesticidas mais comercializada no mundo. Estes compostos geralmente são ésteres que contêm um anel dimetilciclopropano com grupamentos variáveis e a presença de anéis aromáticos. Cada vez mais os cientistas vêm explorando a diversidade microbiana na biodegradação de pesticidas e neste contexto, o emprego de fungos de ambiente marinho possui grande potencialidade devido ao seu sistema enzimático único com a presença de compostos altamente oxigenados e halogenados, assim como o esfenvalerato empregado neste trabalho. Entretanto, estes micro-organismos não têm sido explorados na biotransformação de pesticidas piretróides. Neste estudo foi avaliada a eficiência de fungos de ambiente marinho [Penicillium raistrickii CBMAI 931, Aspergillus sydowii CBMAI 935, Cladosporium sp. CBMAI 1237, Microsphaeropsis sp. Dr(A)6, Acremonium sp. Dr(F)1, Westerdykella sp. Dr(M2)4 e Cladosporium sp. Dr(M2)2] na degradação do pesticida piretróide esfenvarelato. Observou-se que o esfenvalerato e seus principais metabólitos de degradação causam efeitos inibitórios significativos no crescimento dos fungos, mas não o suficiente para inviabilizar o estudo da biodegradação por meio destes micro-organismos. Os resultados obtidos sugerem que diversas espécies fúngicas contribuem para a biodegradação do pesticida esfenvalerato, entretanto a eficiência da degradação deste composto varia muito entre linhagens. Observou-se a degradação de 3 a 35% de 100 mg.L-1 de esfenvalerato presente na formulação comercial (SUMIDAN 150SC®) em 14 dias para diferentes fungos. Os metabólitos identificados [3-fenoxibenzaldeído, ácido 3-fenoxibenzoico, álcool 3-fenoxibenzílico e ácido 3-(hidroxifenoxi)benzoico] tornaram possível uma proposta de rota biodegradativa, onde se observou metabólitos cada vez mais polares, aumentando a possibilidade de carreamento para o meio aquoso. Constatou-se que em geral ocorre a formação de grandes quantidade do ácido 3-fenoxibenzoico e do ácido 2-(4-clorofenil)-3-metilbutanoico, compostos considerados tóxicos e que podem causar efeitos nocivos à saúde humana e ao meio ambiente. Para a linhagen Acremonium sp. Dr(F)1 que apresentou os melhores resultados de biodegradação, após 28 dias de cultivo com 100 mg.L-1 de esfenvalerato observou-se 20 mg.L-1 de acido 3-fenoxibenzoico, que posteriormente foi convertido ao ácido 3-(hidroxifenoxi)benzoico. Observou-se também uma biodegradação mais eficiente do princípio ativo esfenvalerato puro do que na formulação comercial, que pode ser causada por diversos fatores, como a toxicidade do xileno presente na formulação comercial ou a adsorção do esfenvarelato aos componentes da formulação emulsionável dificultando a ação enzimática. A partir destes resultados toma-se interessante o emprego destes micro-organismos visando a biorremediação deste pesticida. / Since the green revolution in the 1950s, the traditional agricultural production has undergone changes such as the intensive use of pesticides, including pyrethroids, which is the third most sold chemical class of pesticide. These compounds are generally esters containing a dimethylcyclopropane ring with different groups and aromatic rings. Scientists are exploring the microbial diversity for the biodegradation of pesticides. The use of marine fungi may show great potential to an efficient biodegradation, because of its unique enzymatic system and the presence of halogenated and oxygenated compounds, such as the pesticide esfenvalerate used in this work. However, these microorganisms have not been explored in the biotransformation of pyrethroid pesticides. In this study, marine-derived fungi [Penicillium raistrickii CBMAI 931, Aspergillus sydowii CBMAI 935, Cladosporium sp. CBMAI 1237, Microsphaeropsis sp. Dr(A)6, Acremonium sp. Dr(F)1, Westerdykella sp. Dr(M2)4 and Cladosporium sp. Dr(M2)2] were applied in the biodegradation of the esfenvalerate. It was observed that the esfenvalerate and its degradation metabolites cause an inhibitory effect on the fungi growth, however not enough to make unfeasible the study of the biodegradation by these microorganisms. The results suggest that different fungal species contribute to the degradation of esfenvalerate, although the efficiency of degradation varies widely between strains. It was observed 3-35% of degradation at a concentration of 100 mg.l-1 of esfenvalerate present in the commercial formulation (SUMIDAN 15OSC®) in 14 days. The identified metabolites [3-phenoxybenzaldehyde, 3-phenoxybenzoic acid, 3- phenoxybenzyl alcohol and 3-(hydroxyphenoxy)benzoic acid ) enabled the proposal of a biodegradative pathway, in which was noted the increasingly polar character of metabolites, raising the possibility of entrainment for aqueous medium . It was observed, in general, the large formation of 3- phenoxybenzoic and 2-(4-chlorophenyl)-3-methylbutanoic acid, compounds that are considered toxic and may cause harmful effects to human health and the environment. For the strain Acremonium sp. Dr (F)1, which showed the best results of 100 mg.l-1 esfenvalerate biodegradation after 28 days, it was observed 20 mg.l-1 of 3-phenoxybenzoic acid, which was later converted to 3- (hydroxyphenoxy)benzoic acid. It was also observed a more efficient biodegradation of the pure active ingredient than the commercial formulation, what can be caused by various reasons, such as the toxicity of the xylene present in the commercial formulation or the esfenvarelate adsorption in the components of the emulsifiable formulation, difficulting the enzymatic activity. These results shows the potential use of these microorganisms in the bioremediation of esfenvalerate.

Populations of Cimex lectularius, the bed bug, have resurged around the world posing significant challenges for pest management professionals and causing physical, economic, and emotional strife. Pyrethroid resistance has been found in the vast majority of populations making pest management more difficult. The objectives of my dissertation research were to document the evolution of resistance to pyrethroid and neonicotinoid combination products (called combination products here) and to a neonicotinoid in the laboratory, to record potential fitness costs to resistance to the combination products, and to compare the efficacy of nine insecticides on six populations. In the laboratory, populations of bed bugs evolve resistance rapidly to a combination product and that resistance translates into cross resistance to another combination product. In a follow up experiment, resistance to a neonicotinoid occurred after three generations of selection. Cross resistance between neonicotinoid and pyrethroid resistance was also found, likely due to a common detoxification mechanism (cytochrome P450 mediated metabolism). Resistance was associated with life history costs in three populations that had been selected with a combination product. Therefore, in the absence of selection pressure, populations of bed bugs should revert towards increasing susceptibility. Two pyrethroid products and three combination products were effective at killing three populations of bed bugs but were relatively ineffective against three other populations. However, the combination product, Transport GHP®, the single action pyrrole product, Phantom SC®, and the single action desiccant, CimeXa®, killed 95 to 100% of all populations investigated over a 14-day exposure. Taken together, results reported in this dissertation suggest that insecticide resistance management may be a useful tool for extending the efficacy of insecticides for control of C. lectularius.

Desde a revolução verde, na década de 1950, o processo tradicional de produção agrícola passou por mudanças com a inserção do uso intensivo de agrotóxicos como os piretróides, que são a terceira classe química de pesticidas mais comercializada no mundo. Estes compostos geralmente são ésteres que contêm um anel dimetilciclopropano com grupamentos variáveis e a presença de anéis aromáticos. Cada vez mais os cientistas vêm explorando a diversidade microbiana na biodegradação de pesticidas e neste contexto, o emprego de fungos de ambiente marinho possui grande potencialidade devido ao seu sistema enzimático único com a presença de compostos altamente oxigenados e halogenados, assim como o esfenvalerato empregado neste trabalho. Entretanto, estes micro-organismos não têm sido explorados na biotransformação de pesticidas piretróides. Neste estudo foi avaliada a eficiência de fungos de ambiente marinho [Penicillium raistrickii CBMAI 931, Aspergillus sydowii CBMAI 935, Cladosporium sp. CBMAI 1237, Microsphaeropsis sp. Dr(A)6, Acremonium sp. Dr(F)1, Westerdykella sp. Dr(M2)4 e Cladosporium sp. Dr(M2)2] na degradação do pesticida piretróide esfenvarelato. Observou-se que o esfenvalerato e seus principais metabólitos de degradação causam efeitos inibitórios significativos no crescimento dos fungos, mas não o suficiente para inviabilizar o estudo da biodegradação por meio destes micro-organismos. Os resultados obtidos sugerem que diversas espécies fúngicas contribuem para a biodegradação do pesticida esfenvalerato, entretanto a eficiência da degradação deste composto varia muito entre linhagens. Observou-se a degradação de 3 a 35% de 100 mg.L-1 de esfenvalerato presente na formulação comercial (SUMIDAN 150SC®) em 14 dias para diferentes fungos. Os metabólitos identificados [3-fenoxibenzaldeído, ácido 3-fenoxibenzoico, álcool 3-fenoxibenzílico e ácido 3-(hidroxifenoxi)benzoico] tornaram possível uma proposta de rota biodegradativa, onde se observou metabólitos cada vez mais polares, aumentando a possibilidade de carreamento para o meio aquoso. Constatou-se que em geral ocorre a formação de grandes quantidade do ácido 3-fenoxibenzoico e do ácido 2-(4-clorofenil)-3-metilbutanoico, compostos considerados tóxicos e que podem causar efeitos nocivos à saúde humana e ao meio ambiente. Para a linhagen Acremonium sp. Dr(F)1 que apresentou os melhores resultados de biodegradação, após 28 dias de cultivo com 100 mg.L-1 de esfenvalerato observou-se 20 mg.L-1 de acido 3-fenoxibenzoico, que posteriormente foi convertido ao ácido 3-(hidroxifenoxi)benzoico. Observou-se também uma biodegradação mais eficiente do princípio ativo esfenvalerato puro do que na formulação comercial, que pode ser causada por diversos fatores, como a toxicidade do xileno presente na formulação comercial ou a adsorção do esfenvarelato aos componentes da formulação emulsionável dificultando a ação enzimática. A partir destes resultados toma-se interessante o emprego destes micro-organismos visando a biorremediação deste pesticida. / Since the green revolution in the 1950s, the traditional agricultural production has undergone changes such as the intensive use of pesticides, including pyrethroids, which is the third most sold chemical class of pesticide. These compounds are generally esters containing a dimethylcyclopropane ring with different groups and aromatic rings. Scientists are exploring the microbial diversity for the biodegradation of pesticides. The use of marine fungi may show great potential to an efficient biodegradation, because of its unique enzymatic system and the presence of halogenated and oxygenated compounds, such as the pesticide esfenvalerate used in this work. However, these microorganisms have not been explored in the biotransformation of pyrethroid pesticides. In this study, marine-derived fungi [Penicillium raistrickii CBMAI 931, Aspergillus sydowii CBMAI 935, Cladosporium sp. CBMAI 1237, Microsphaeropsis sp. Dr(A)6, Acremonium sp. Dr(F)1, Westerdykella sp. Dr(M2)4 and Cladosporium sp. Dr(M2)2] were applied in the biodegradation of the esfenvalerate. It was observed that the esfenvalerate and its degradation metabolites cause an inhibitory effect on the fungi growth, however not enough to make unfeasible the study of the biodegradation by these microorganisms. The results suggest that different fungal species contribute to the degradation of esfenvalerate, although the efficiency of degradation varies widely between strains. It was observed 3-35% of degradation at a concentration of 100 mg.l-1 of esfenvalerate present in the commercial formulation (SUMIDAN 15OSC®) in 14 days. The identified metabolites [3-phenoxybenzaldehyde, 3-phenoxybenzoic acid, 3- phenoxybenzyl alcohol and 3-(hydroxyphenoxy)benzoic acid ) enabled the proposal of a biodegradative pathway, in which was noted the increasingly polar character of metabolites, raising the possibility of entrainment for aqueous medium . It was observed, in general, the large formation of 3- phenoxybenzoic and 2-(4-chlorophenyl)-3-methylbutanoic acid, compounds that are considered toxic and may cause harmful effects to human health and the environment. For the strain Acremonium sp. Dr (F)1, which showed the best results of 100 mg.l-1 esfenvalerate biodegradation after 28 days, it was observed 20 mg.l-1 of 3-phenoxybenzoic acid, which was later converted to 3- (hydroxyphenoxy)benzoic acid. It was also observed a more efficient biodegradation of the pure active ingredient than the commercial formulation, what can be caused by various reasons, such as the toxicity of the xylene present in the commercial formulation or the esfenvarelate adsorption in the components of the emulsifiable formulation, difficulting the enzymatic activity. These results shows the potential use of these microorganisms in the bioremediation of esfenvalerate.