Brief Summary of Minutes of Annual Meeting

Jack Watson served as Chair of the committee and Joe Pignatello served as Secretary. The Administrative Advisor, Lee Sommers, summarized the vision and roles of NIFA and discussed the AFRI grants program. It was determined by consensus of the attending members that next year's meeting would be hosted by Shad Nelson of Texas A&M, in Corpus Christie, in January 2012. Each participant provided a research update, with discussion following each presentation. Dr. Dick Green, a former member of W-82 stopped by to greet the attending members; a pleasant surprise.

Objective 1: To identify and quantify fundamental chemical, physical, and biological processes relevant to pesticides and contaminants in agricultural ecosystems I. USDA-ARS - Arizona A. Influence of pKa Accomplishment/output: Contaminants such as antibiotics, found in treated effluent, have been identified as a potential problem for use of this water for irrigation due to the potential for development of antibiotic resistance. Initial environmental fate parameters were determined for lincomycin in soils. It was found that lincomycin sorption is related to soil pH. When soil pH is below 7.6 lincomycin is highly mobile, however, when soil pH is above 7.6 mobility was significantly reduced. These results can be used to determine site-specific guidelines for disposal and use of reclaimed water. B. Development of Antibiotic Resistance Accomplishment/output: Most wastewater treatment plants are not designed for the removal of residual antibiotics, which can be released into the environment with treated wastewater, increasing public health concerns for the potential for development of antibiotic resistance (AR) in soil bacteria. We are comparing levels of resistance to 16 antibiotics in soil bacteria isolated from water storage basins recharged with either reclaimed water or natural groundwater in central Arizona. Initial results suggest that resistance to multiple antibiotics, including tetracycline, daptomycin, and erythromycin, exists in both soils. Overall AR is not increased in soils exposed to reclaimed water. II. California - Riverside A. Bioavailability and phase partitioning: Accomplishment/output: 1. The effect of dissolved organic carbon (DOC) on pyrethroid sorption to sediment was essentially linear. Interactions between DOC and pyrethroids decreased sorption of some pyrethroids even further, implying that DOC-pyrethroid complexes were relatively stable in solution. DOC sources with higher contents of carboxylic and phenolic groups were found to have a higher potential to associate with pyrethroids. 2. We evaluated biodegradation of pyrene by Mycobacterium vanbaalenii PYR-1 as a function of sediment particle sizes. Analyses showed that the total organic carbon (TOC), black carbon (BC), and specific surface area (SSA) of the specific particle size fractions, instead of the particle size scale itself, were closely related with the mineralization rate. Subsequent model analysis showed that pyrene sorbed on silt and clay aggregates was directly utilized by the degrading bacteria. 3. Accurate measurement of adsorption coefficients for Polybrominated diphenyl ethers (PBDEs) using conventional batch methods can be confounded by biases caused by their sorption to dissolved organic carbon (DOC). Sorption isotherms were constructed for BDE-47 and BDE-99 in sediments by using different methods to measure the aqueous phase concentration Cw. This study showed that PBDE congeners have larger sorption coefficients than would be measured by the conventional method. B. Pesticide sorption and washoff on concrete: Accomplishment/output: We evaluated the dependence of washable pesticide residues on pesticide types, formulations, time exposed to outdoor conditions and number of washing cycles. Wash-off potential was consistently higher for solid formulations than for liquid formulations. Trace levels of pyrethroids were detected in the wash-off solution even after 14 washing-drying cycles over 42 d under outdoor conditions. We characterized sorption and desorption of permethrin, the most used pyrethroid insecticide. Sorption of 14C-permethrin to concrete was rapid, and the sorption isotherm was linear, with surface area-normalized Kd of 1.91 ± 0.1 mL/cm2. Permethrin became more resistant to desorption as the pesticide contact time on the concrete increased. When pesticide-treated concrete surfaces come in contact with runoff water, elevated concentrations may be expected initially, while the extended desorption implies a potential for sustained contamination. III. Minnesota USDA-ARS: Accomplishment/output: An enrichment culture approach was used to isolate a pure culture of the yeast Candida xestobii, which had the ability to use the herbicides metolachlor and alachlor as asole source of carbon for growth. LC-ESI-MS analyses indicated that C. xestobii degraded 60% of the added metolachlor after 4 d of growth, and converted up to 25% of the compound into CO2 after 10 days. A bacterium, Bacillus simplex, was also found to have the ability to catabolize metolachlor and use this herbicide as a sole source of carbon for growth. IV. Minnesota  Univ of Mn A. Biodegradation and Mineralization Accomplishment/output: We examined 10 and 2 year histories of metolachlor and S-metolachlor applications, respectively, for microorganisms that had the ability to degrade this herbicide. Pure cultures of C. xestobii degraded 60% of the added metolachlor after 4 d of growth, and converted up to 25% of the compound into CO2 after 10 days. In contrast, pure cultures of B. simplex biodegraded 30% of metolachlor following 5 d of growth in minimal medium. Yeast degraded other acetanilide compounds and 80% of acetochlor and alachlor were degraded after 15 h and 41 h of growth, respectively. B. Bioavailability-Organoclay Formulations Accomplishment/output: Pesticide formulations based on organoclays have been proposed to prolong the efficacy and reduce the environmental impact of pesticides in soil. This research addressed the question of whether atrazine in organoclay-based formulations is irreversibly sorbed or is bioavailable for bacterial degradation in soil. Bound residues increased from <4% at day 0 to ~17% after the 2 week incubation for both the formulated and free forms of atrazine. C. X-Ray structure and mutational analysis of TrzN. Accomplishment/output: Atrazine chlorohydrolase, TrzN, initiates bacterial metabolism of the herbicide atrazine by hydrolytic displacement of a chlorine substituent from the s-triazine ring. The present study describes crystal structures and reactivity of wild-type and active site TrzN mutant enzymes. The structure and kinetics are reminiscent of carbonic anhydrase that uses a threonine to assist in positioning water for reaction with carbon dioxide.Both structure and kinetic determinations suggest that the E241 side chain provides a proton to N-1 of the s-triazine substrate to facilitate nucleophilic displacement at the adjacent C-2. D. Bacterial Ammeline Metabolism Accomplishment/output: Melamine toxicity in mammals is due to the blockage of kidney tubules by insoluble complexes of melamine with cyanuric acid or uric acid. Bacteria metabolize melamine via three consecutive deamination reactions to generate cyanuric acid. The second deamination reaction, in which ammeline is the substrate, is common to many bacteria, but the genes and enzymes responsible have not been previously identified. In this study we used a combination of bioinformatics and experimental data to identify guanine deaminase as the enzyme responsible for this biotransformation. V. Missouri Veterinary Antibiotic Sorption Accomplishment/output: The potential of veterinary antibiotics (VAs) to impact human and environmental health requires the development and evaluation of land management practices that mitigate VA loss from manure-treated agroecosystems. Vegetative buffer strips (VBS) are postulated to be one management tool that can reduce VA transport to surface water resources. Oxytetracycline (OTC) was strongly adsorbed by all soils considered (agroforestry buffer, grass buffer, and cropland soil) and was not readily extractable. OTC and sulfadimethoxine (SDT) solid to solution partition coefficients are significantly greater for soils planted to VBS relative to grain crops. Significant differences in OTC and SDT Kd values were also noted among the soil series studied. Clay content and pH were the most important soil properties controlling OTC and SDT adsorption, respectively. Agroforestry and grass buffer strips may effectively mitigate antibiotic loss. VI. Kentucky A. Livestock antibiotics Accomplishment/output: Experiments were undertaken to determine the level at which three antibiotics would have adverse effects on selected indicators. Changes in NO3- and NO2-, N2O gas, and fatty acid methyl ester (FAME) levels in soils were measured to assess antibiotic affects on nitrification, denitrification, and microbial community structure, respectively. Bacitracin did not inhibit nitrification in the soils at any concentration up to 500 mg/kg compared to the zero level control. Roxarsone inhibited nitrification at >150 mg/kg in the shoulder and back slope positions and at 500 mg/kg at all the positions, but not at lower concentrations. Virginiamycin inhibited nitrification at >5 mg/kg in the shoulder, >15 mg/kg at backslope and >50 mg/kg at all positions. Bacitracin inhibited denitrification at 500 mg/kg soil, however, virginiamycin and roxarsone did not inhibit denitrification any concentration up to 500 mg/kg. Bacitracin did not affect any of the 60 FAMEs compared to the zero level control. Roxarsone and virginiamycin at 1 mg/kg also did not affect any of the FAMES. Roxarsone at 100 mg/kg increased two monounsaturated FAMEs and decreased one monounsaturated FAME, and virginiamycin at 100 mg/kg increased two monounsaturated FAMES and decreased branched monounsaturated FAME and polyunsaturated FAME 26:0. B. Sorption and resistance Accomplishment/output: Batch equilibrium sorption experiments were conducted to determine the extent that soils retained bacitracin, roxarsone, and virginiamycin in the concentration range 0-1500 mg/kg soil. Results showed that soils most strongly retained bacitracin followed by virginiamycin and roxarsone. To determine whether native soil microorganisms were resistant to antibiotics, microbes were extracted from soil, exposed to increasing levels of antibiotics in liquid culture media, and evaluated for growth from changes in turbidity in culture tubes over three days. Results showed that microbial growth was high and not affected at concentrations up to 100 mg/L solution compared to zero level control. VII. Colorado A. Transport Accomplishment/output: A field-scale study was conducted to assess the potential for runoff of seventeen different hormones, including androgens, estrogens, and progestogens from an agricultural field applied with biosolids and the major mechanisms controlling hormone transport during simulated rainfall events. Whole water runoff samples prior to biosolids application had low concentrations of a few hormones. In contrast, significantly higher concentrations of multiple estrogens, androgens, and progesterone were observed in runoff samples taken 1, 8 and 35 days after biosolids application. Androgen runoff concentrations declined from day 1 to day 35 after biosolids application but the concentrations, in particular for androstenedione, observed 35 days after biosolids application were still higher than concentrations known to affect the endocrine system of aquatic organisms. A significant positive correlation was observed between rainfall amount and hormone mass fluxes. Hormones in runoff were primarily present in the aqueous phase. B. Biodegradation Accomplishment/output: The potential for biodegradation of testosterone, 17²-estradiol (E2) and progesterone by swine (Sus scrofa) manure-borne bacteria was examined. The impact of temperature, pH (6, 7, and 7.5), glucose amendments (0, 3, and 22 mmol L1), and presence of oxygen on testosterone degradation kinetics was determined. Testosterone, 17²-estradiol and progesterone were biodegraded within 25 h of reaction initiation under aerobic conditions. The half-life (t1/2) for the degradation of testosterone under anaerobic conditions was six times longer than aerobic conditions. Testosterone degradation was found to significantly increase when incubated at 37°C vs. 22°C. The impact of pH and glucose amendments on the testosterone degradation rate were found to be small. Six DNA sequences of bacteria from the Proteobacteria phylum widely distributed among six different genera - Acinetobacter, Brevundimonas, Comamonas, Sphingomonas, Stenotrophomonas, and Rhodobacter were identified in a testosterone-degrading enriched culture. Six degradation products of testosterone were identified. One important observation in this study is that more than 48% of the 14C-testosterone had been mineralized to 14CO2 within 8 d of incubation. The high percentage of 14C-testosterone converted to 14CO2 suggests that testosterone served as an energy source. VIII. Michigan A. Environmental Pharmaceuticals Accomplishment/output: We investigated the occurrence and fate of four commonly used veterinary pharmaceuticals (amprolium, carbadox, monensin and tylosin) in an animal farm in Michigan. Amprolium and monensin were frequently detected in nearby surface waters, whereas tylosin or carbadox was rarely found. These pharmaceuticals were more frequently detected in surface runoff during the non-growing season than during the growing season. Pharmaceuticals resulting from post-harvest manure application appeared to be more persistent than those from spring application. High concentrations of pharmaceuticals in soils were generally observed in the sites where the respective concentrations in water were also high. Results suggest that soil is a sink for veterinary pharmaceuticals that can be disseminated to nearby surface waters. An analytical method was developed to quantitatively determine pharmaceuticals in biosolid (treated sewage sludge) from wastewater treatment plants (WWTPs). For the fifteen target pharmaceuticals commonly found in the environment, the overall method recoveries ranged from 49% to 68% for tetracyclines, 64% to 95% for sulfonamides, and 77% to 88% for other pharmaceuticals. The developed method was successfully validated and applied to the biosolid samples collected from WWTPs located in six cities in Michigan. Among the fifteen target pharmaceuticals, fourteen pharmaceuticals were detected in the collected biosolid samples. B. Sorption and Transformation Accomplishment/output: Cation exchange was the primary mechanism responsible for lincomycin sorption by soil clay minerals. The presence of Ca2+ in solution diminished lincomycin sorption. Clay interlayer hydration status strongly influenced lincomycin adsorption. Strongly hydrated exchangeable cations resulted in a more hydrated clay interlayer environment reducing sorption in the order of Ca- < K- < Cs-smectite. X-ray diffraction revealed that lincomycin was intercalated in smectite clay interlayers. Sorption capacity was limited by clay surface area rather than by cation exchange capacity. MnO2 caused rapid and extensive oxidative decomposition of clindamycin and lincomycin in aqueous solution. The presence of electrolyte and dissolved organic matter in aqueous solution, and increase of solution pH, diminished lincosamide binding to MnO2. Smectites, especially Cs-saponite, effectively adsorbed dibenzo-p-dioxin (DD) from water. Adsorption was promoted by exchangeable cations with low hydration energies, and negative charge in the smectite arising from the tetrahedral siloxane sheets. X-ray diffraction measurements revealed that as DD loading increased to e 8,000 mg/kg the clay basal spacing increased abruptly from 12.3 to 15.2 Å demonstrating DD intercalation. The 12.3 Å spacing provides an interlayer distance that closely matches the molecular thickness of DD. Fourier transformation infrared measurements confirm that adsorbed DD is present in orientations that are not parallel with the interlayer planar siloxane surfaces of smectite. C. Remediation Accomplishment/output: A novel method was developed for synthesizing subnano-sized zero-valent iron (ZVI) using smectite clay layers as templates. The clay-templated ZVI showed superior reactivity and efficiency compared to other previously reported forms of ZVI as indicated by the reduction of nitrobenzene; structural Fe within the aluminosilicate layers was nonreactive. This new form of subnano-scale ZVI may find utility in the development of remediation technologies for persistent environmental contaminants. Clay minerals were employed as template-supporting matrices to synthesize nano-scaled ZVI. The reactivity of the ZVI was evaluated based on the rate and extent of reduction of nitrobenzene to aniline. The results revealed that the reactivity of ZVI decreased with increasing particle sizes, and the ZVI intercalated in smectite clay manifested the highest reactivity. The reaction efficiency of the ZVI associated with smectite clay was estimated to be as high as 90%. IX. South Dakota A. Tylosin and chlortetracycline Accomplishment/output: Veterinary pharmaceuticals are commonly administered to animals for disease control and added into feeds at subtherapeutic level to improve feeding efficiency and are excreted in manure. The effects of these compounds on swine manure digestion in the presence and absence of the biocide sodium azide were studied. CTC enhanced initial hydrolysis reactions through volatile suspended solids productions, while inhibiting methane and carbon dioxide production. Tylosin did not affect methane and carbon dioxide production; however, the relative abundance of both hydrogen utilizing and acetate-only utilizing microbial populations were compromised. Sodium azide in the absence of antibiotics enhanced metabolic output and initial biomass productions, and this suggests that populations of Methanobacteriales and Methanosaetaceae spp. appeared to contain sufficient periplasmic bound reductase to effectively utilize acetate and hydrogen in the presence of sodium azide. B. GC-Clamp primer batches Accomplishment/output: Fingerprinting methods such as denaturing gradient gel electrophoresis (DGGE) have become a popular tool for the analysis of microbial communities. Three repeat syntheses of the same GC clamp primer, and two different GC clamp primers directed at the V3-5 region of the 16S rRNA gene were compared. Genomic DNA of two separate soil bacterial communities, and three bacterial species were amplified and resolved by DGGE. The DGGE profiles obtained with repeat-synthesized primers differed among each other as much as with alternate primers, for both soil DNA and pure single species. The GC clamp portion of members of amplicon pools varied among each other, deviating from the design sequence. C. Influence of chlortetracycline (CTC) Accomplishment/output: CTC is not sorbed or degraded in animals and is excreted in a bioactive form. Therefore, CTC may enter the environment through land-spreading of manure. This study determined the influence of a single application of manure with or without CTC on field soil microbial community characteristics. Manures from swine fed unamended or CTC-amended rations were applied to a soil that had no previous manure application history. Soil samples were analyzed for aerobic culturable counts on R2A agar and most probable number using 2,4-D as a sole carbon source. Soil extracts at 1, 7, and 42 d after application were subjected to denaturing gradient gel electrophoresis analysis of the V3 region of the 16S rRNA gene pool. Gels were analyzed using Neighbor Joining based on Euclidean distance and Raup-Crick multivariate statistical analyses and selected bands were extracted to identify predominant community members. X. Hawaii Transport of Cryptosporidum parvum oocysts Accomplishment/output: In order to gain more information about the fate of Cryptosporidium parvum oocysts in tropical volcanic soils, the transport and attachment behaviors of oocysts and oocyst-sized polystyrene microspheres were studied in the presence of two soils of differing chemical and physical properties. A third agricultural soil from Illinois was included for reference. Although a high (99%) removal of oocysts and microsphere within a volcanic ash soil occurred initially, transport was merely retarded because of highly reversible interactions with grain surfaces. This suggests contaminated volcanic ash soil could serve as a reservoir for subsequent contamination of groundwater. Because of the highly reversible nature of organic colloid immobilization in this soil type, C. parvum could contaminate surface water should overland flow pick up near-surface grains to which they are attached. XII. New Jersey Sorption and Redox Reactions Accomplishment/output: (1) The sorption of testosterone and androstenedione was nonlinear, and the log KOC values for testosterone and androstenedione are higher at lower aqueous phase concentrations. (2) For the three pesticides, atrazine, metolachlor and napropamide, humic acids (HA) and base extracted soil (BE), and particulate organic matter (POM) of the demineralized BE were used as sorbents. The herbicides sorption isotherms were nonlinear for the BE and POM, but relatively linear for HA. The isolated POM was an exceptionally good sorbent for the herbicides, and played a more important role than HA in the sorption of herbicides. Its sorption capacity was diminished in the bulk soil. (3) The measured KD values of tylosin fell into a narrow range between 1.7 and 12 L kg-1 for all the soils. The KD values appeared to correlate well with soil pH, but correlate poorly with the soil organic carbon content. Soil pH appeared to have strong influence on the sorption as tylosin is mainly positively charged at pH < 7.1. (4) Transformation of PCP and BPA by manganese dioxide (MnO2) was examined at different aquatic conditions. Transformation rates of lindane, pentachlorophenol (PCP) and bisphenol A (BPA) were found to be near first order with respect to the pollutant concentration, [MnO2] and [H+], respectively. Background divalent electrolytes considerably decreased the reaction. Dimers were detected as products for both systems. (5). Transformations of alpha-, beta-, and gama-hexachlorocyclohexanes (HCHs) were examined. In the absence of FeS, highly pH- and temperature-dependent reaction rates were observed for alpha- and gama-HCH, and pentachlorocyclohexene (PCCH) and 1,2,4- and 1,2,3- trichlorobenzene (TCB) were detected as the intermediate and final products of the transformation of both alpha- and gama-HCH. The calculated activation energies (Ea) at pH 9.26 were 60.4 ± 7.8 and 67.7 ± 8.7 kJ mol-1, respectively, for alpha- and gama-HCH. In the presence of FeS, transformation rates were dramatically enhanced, and both alpha- and gama-HCH isomers were degraded with petachlorocyclohexene (PCCH) and tetrachlorocyclohexene (TeCCH) as their respective intermediate products. Trichlorobenzenes (TCBs), dichlorobenzenes (DCBs), and chlorobenzene (CB) were detected as the final products for both HCH isomers. XIII. Connecticut A. Sulfamethazine Adsorption Accomplishments/Output: We studied the adsorption of the heavily used swine antibiotic sulfamethazine (SMZ) to a range of biochars. The ability of biochar to increase the apparent solids-water distribution coefficient of SMZ when added to soil was significant and trended with the biochar specific surface area. Adsorption by the most effective biochar was studied in detail in the absence of soil. The isotherm at pH 5 was highly nonlinear and gave Kd values that ranged from ~ 104 to 101 times greater than literature KOC values for SMZ. Sorption was greatest at about pH 5 where SMZ0 predominates; however, sorption at pH values where SMZ+ and SMZ- predominate was far greater than predicted by their respective Kow. Competition experiments indicated that sorption was driven primarily by nonspecific effects. B. Phenolic Acids Adsorption Accomplishments/Output: Depending on biomass source material and formation conditions black carbon (biochar) can be a strong adsorbent of organic compounds. Aromatic and phenolic carboxylic acid compounds exuded by plant roots play important roles in soil biology and allelopathy, and carboxylate functional groups are abundant in soil organic matter. We studied the adsorption of cinnamic and coumaric acids to different commercial biochar prototypes at pH above 6.9 where the acids are >99% dissociated. Isotherms were highly nonlinear, and give biochar-water distribution ratios up to 104 L/kg. Adsorption intensity trended with surface area and generally followed the order coumarate > cinnamate. Isotherms in unbuffered biochar-water mixtures became progressively suppressed relative to isotherms in buffered mixtures as equilibrium solute concentration increased. C. Cross-linking of Humic Acid with Organic Cross-linkers. Accomplishments/Output: The formation of intermolecular links between humic molecules and between strands within a humic molecule is referred to as cross-linking. Crosslinking increases molecular weight, lowers solubility, inhibits biodegradation, reduces molecular flexing within the organic solid phase, and influences the sorbent properties of organic matter. Two different organic cross-linking agents were used to cross-link a soil humic acid (HA). For diepoxide, the FTIR spectra showed the disappearance of the epoxy bands and the appearance of persistent bands associated with the aliphatic and C=O bands of the cyclohexyl groups. For 1,2,3,4-butanetetracarboxylic acid (BTCA), FTIR spectra showed bands signifying, i) the transient appearance of expected cyclic anhydride intermediates, ii) the disappearance of NaH2PO2, and iii) enhancement of C=O signal corresponding to incorporated BTCA group. In water buffered at pH 6 the solubility of both the DE- and BTCA-crosslinked HA was far lower than the solubility of HA itself, signifying extensive cross-linking. XIV. Pennsylvania Outputs: Sample cleanup and concentration procedures were worked out for soil samples such that we have confidence in results. . Experiments were conducted to determine the distribution of carbamazepine though the top 120 cm of forested, grassed and cropped lands. Results indicated that the amount of soil water contained in this depth was approximately equal to one years worth of irrigation, while the amount of carbamazepine was equivalent to approximately 15 years of application. In addition, the distribution of carbamazepine was concentrated near the soil surface, consistent with its strong sorption to organic carbon. Likely due to its high organic carbon content, forested lands had the highest concentration of carbamazepine. Approximately a 5% - 10% signal degradation occurs when antimicrobials are added to standards. This represents an important consideration in conducting analyses of soil extracts preserved with antimicrobials. XV. California  Berkley Outputs: Analysis of the As speciation of the batch cultures in conjunction with the time-course of each abiotic treatment provided temporal information about which As species are formed in marine algae. Our data reveal edge effects of As uptake with enhanced As uptake as a function of P concentration. Arsenic hot spots were observed in cross-sectioned samples. Calcium also appears to be positively correlated with increased P concentration toward the edge of the disc. Objective 2: Integrate chemical and biological process information for use in models applicable across different spatial and temporal scales. I. Hawaii A. Transport Accomplishment/output: Experiments were conducted to examine the leachability of two estrogen hormones (17-beta estradiol [E2] and estrone [E1]) through small packed columns of three soils from Oahu, Hawaii. Both saturated and unsatured flow and transport experiments were conducted. Early arrival of E1 and E2 were observed in cinder compared to the Oxisol or the Mollisol. Both compounds showed enhanced transport in presence of lagoon effluent. E1 concentration in the column effluent was lower in saturated conditions than under unsaturated conditions. Also, batch sorption experiments were conducted for these two chemicals with and without microbial inhibitors (e.g., sodium azide) along with an antibiotic (chloramphenicol) and irradiation of the soil. Equilibrium was not achieved in 7 days in any of the soils for E2 alone or E1 and E2 combined. Microbial inhibition, including soil radiation did not completely remove this problem. B. Leaching and Runoff Accomplishment/output: Hawaii studied the behavior of the termiticide fipronil in Hawaii soils to assess its potential to contaminate ground and surface water. They characterized (1) adsorption, (2) transport, and (3) degradation. The concentration of fipronil in the leachate from the three soils correlated inversely with soil organic carbon content. Fipronil showed large losses through leaching, but small losses via runoff due to low volumes of runoff water generated and/or negligible particle-facilitated transport of fipronil. The half-life values of fipronil in all three soils were similar. Objective 3. Provide stakeholders with tools for developing strategies to ensure sustainable agriculture and to protect natural resource systems. I. Hawaii Registration of New Chemicals Accomplishment/output: Hawaii used data from studies to evaluate leaching, potential loss to runoff water, and ecotoxicological impacts, and provides that data to the state regulatory agency for action. If the compound appears to have significant impact to the local environment, it may be registered as a restricted use compound or the state requires that a certified applicator be responsible for its use. In that way, the state keeps track of the amount used and the locations treated.

Trigo, C., W.C. Koskinen, C. Rafael, M.J. Sadowsky, M.C. Hermosin, and J. Cornejo. 2010. Bioavailability of Organoclay Formulations of Atrazine in Soil. J. Agric. Food Chem., 2010, 58 (22), pp 1185711863. Munoz, A., W. C. Koskinen, L. Cox, and M. J. Sadowsky. 2011. Degradation of the herbicides metolachlor and alachlor by Candida xestobii. J. Agric. Food Chem. 58: (in press). Koskinen, W. C. and H. H. Cheng. 2011. Effects of Aging on Bioreactive Chemical Retention, Transformation, and Transport in Soil. J. Soils Sed. (in press) Williams, C.F., T.A. Coffelt and J.E. Watson. 2009. Increased soil sorption of Pendimethalin due to deposition of guayule-derived detritus. Soil Sci. Soc. Am. J. 73:1952-1957. Walker, C.W. and J.E. Watson. 2010. Adsorption of estrogens on laboratory materials and filters during sample preparation. J. Envir. Qual. 39:744-748. Jiang, W., K. Lin, D. Haver, S. Qin, F. Spurlock, and J. Gan. 2010. Wash-off potential of urban use insecticides on concrete surfaces. Environmental Toxicology and Chemistry 29: 1203-1208. Nillos, M.G., S.J. Qin, C. Larive, D. Schlenk, and J. Gan. 2009. Epimerization of cypermethrin stereoisomers in alcohols. Journal of Agricultural & Food Chemistry 57: 6938-6943. Nillos, M.G., J. Gan, and D. Schlenk. 2010. Chirality of organophophorus pesticides: Analysis and toxicity. Journal of Chromatography B 878:1277-1284. Han, A.L., Y. Ling, Z. Li, H.Y. Wang, Y. Wang, Q.F. Ye, L. Lu, and J. Gan. Plant availability and phytotoxicity of soil bound residues of herbicide ZJ0273, a novel acetolactate synthase potential inhibitor. Chemosphere 77: 955-961. Wang, H.Z., J.M. Xu, S.R. Yates, J.B. Zhang, J. Gan, J.C. Ma, J.J. Wu, and R.C. Xuan. 2010. Mineralization of metsulfuron-methyl in Chinese paddy soils. Chemosphere 78: 335-341. Wang, H.L., K.D. Lin, Z.A. Hou, B. Richardson, and J. Gan. 2010. Sorption of the herbicide terbuthylazine in two New Zealand forest soils amended with biosolids and biochars. Journal of Soils and Sediments 10: 283-289. Wang, W., Q.F. Ye, W. Ding, A.L. Han, H.Y. Wang, L. Lu, and J. Gan. 2010. Influence of soil factors on the dissipation of a new pyrimidynyloxybenzoic herbicide ZJ0273. Journal of Agricultural and Food Chemistry 58: 3062-3067. Zhao, M.R., F. Chen, C. Wang, Q. Zhang, J. Gan, and W.P. Liu. 2010. Integrative assessment of enantioselectivity in endocrine disruption and immunotoxicity of synthetic pyrethroids. Environmental Pollution 158: 19681973. Cui, X.Y., W. Hunter, Y. Yang, Y.X. Chen, and J. Gan. 2010. Bioavailability of sorbed phenanthrene and permethrin in sediments to Chironomus tentans. Aquatic Toxicology 98: 8390. Greenberg, L., M.K. Rust, J.H. Klotz, D. Haver, J.N. Kabashima, S. Bondarenko and J. Gan. 2010. Impact of ant control technologies on insecticide runoff and efficacy. Pest Management Science 66: 980-986. Lao, W.J., and J. Gan. 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