Pesticide Decontamination and Detoxification


Ammonium thiosulfate (ATS) bacterial E C5 0 values ... Aquatic systems, atrazine degradation,. 134. Aquifers ... aquatic and wetland systems, 134 bact...
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Subject Index Acetochlor chemical structures, 201/ replacing alachlor, 200 Activity directed evolution, 32-33 site-directed mutagenesis, 31-32 Acute toxicity test, Vibriofisheri,59 Adjuvants. See Surfactant adjuvants Advanced oxidation processes (AOP), O H radical production, 114-115 Affinity tags, organophosphorus hydrolase (ΟΡΗ) immobilization, 28-29 Agriculture, pesticides, 26, 114 Agrobacterium radiobacter J14a, atrazine-degrading, 148 Air quality, fumigant compounds, 170 Alachlor adsorption to soil and aquifer material, 204-205 aerobic and anaerobic conditions in soil and aquifer, 208/ bacterial EC50 values before and after reaction with thiosulfate salts, 60t chemical structures, 201/ degradation in aerobic vs. anaerobic conditions, 210 degradation in column, 158-159 degradation model, 204 dehalogenation reaction between, and thiosulfate salts, 57/ dissipation in aqueous solutions, 55/ effect of ammonium thiosulfate on leaching, 63/ metabolites under aerobic and anaerobic conditions, 206, 209i, 210

mineralization, 206 organic carbon content and partition coefficients, 207i radioactive regions of thin layer chromatographic plates, 209r relative mobility (Rf value), 205 relative reactivity, 57, 58/ sorption and degradation in aquifers, 210 structures of metabolites, 200, 202/ transformation, 56/ Aldehydes, oxidation, 89 Aliphatic fluoro compounds, defluorination, 192-193 Ammonia, o-phthalaldehyde (ΟΡΑ) precipitation, 88 Ammonium thiosulfate (ATS) bacterial E C values before and after reaction with thiosulfate salts, 60? depletion of fumigants in root zone, 173,176-177 detoxifying halogenated fumigants, 170 subsurface application, 177 See also Fumigants; Thiosulfate salts Anodic Fenton treatment (AFT) A F T kinetic model, 72, 74 analytical methods, 69-70 anion exchange membrane A F T , 77, 79/ apparatus of membrane A F T , 7 8 / application to pesticides, 66-67 atrazine degradation, 70, 72 biodegradability, 80, 82 carbamate pesticides, 80, 8 1 / carbaryl degradation data, 77, 79/ cation exchange membrane A F T , 77, 79/ chemicals, 67 5 0

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250 competitive kinetics, 77, 80 degradation of 2,4-D, 72, 74, 75/ diazinon degradation, 74, 76/ direct and indirect methods, 80, 81/ ethylene thiourea (ETU) degradation, 70 hydroxyl radical reaction rate constants, 81/ improvement to electrochemical Fenton treatment, 66, 70 materials and methods, 67,69-70 membrane AFT, 77 pesticide concentration changes during AFT, 72 pesticide structures, 68/ proposed degradation pathway for atrazine, 73/ structures of ETU and degradation products, 71/ treatment system, 67, 69 Aquatic systems, atrazine degradation, 134 Aquifers herbicide metabolites, 200, 203 materials and methods, 204-205 sorption and degradation of alachlor, 210 vulnerability to herbicide contamination, 203 Atrazine abundance of degrading bacteria, 135/ adsorption to soil and aquifer material, 204-205 Agrobacterium radiobacter, 148 anaerobic conditions, 148-149 anodic Fenton treatment (AFT), 70, 72 aquatic and wetland systems, 134 bacterial degradation mechanisms, 142-143, 146 biologically mediated dehalogenation, 130-131 catabolic genes in environment, 136 chlorohydrolase activity, 41 Clavibacter strain, 146-147

contamination, 141-142 degradation, 200 degradation in column, 158-159 degradation potential in natural environments, 132-134 degrading microorganisms, 144/, 145/ Escherichia coli, 147 evolution of metabolic pathway, 4245 expression of atzB in Pseudomonas ADP as function of medium pH, 151/ focus in phytoremediation, 156 hydrolytic attack, 143, 146 lower biodégradation pathway, 132/ magnetic capture hybridization (MCH), 149-150 metabolism to cyanuric acid, 40-42 mineralization, 136, 146, 206 monitoring bioremediating bacterial in soils, 149-150 most probable number (MPN) method, 149 nitrogen source, 42-43 Nocardioides CI90, 148 organic carbon content and partition coefficients, 207/ oxidative attack, 142-143 PCR-denaturing gradient gel electrophoresis (DGGE) of soil community, 137/ percentage of applied with mulberry trees as vegetation, 160, 161/ phylogenetics of known, metabolizing bacteria, 135-136 proposed degradation pathway for AFT, 73/ Pseudaminobacter CI47, 148 Pseudomonas strain, 146-148 relative mobility (Rf value), 205 soil, 132-134 soil bioremediation using atrazinedegrading bacteria, 146-149 upper biodégradation pathway, 131/ use, 200

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weed control, 130 See also s-Triazine herbicides

Bacteria abundance of atrazine-degrading, 135/ phylogenetics of known atrazine metabolizing, 135-136 3,5,6-trichloro-2-pyridinol (TCP)degrading, 17-18 Basins, slowing runoff flow, 220 Batch experiments, triclosan oxidation, 105-108 Bendiocarb, structure, 68/ Best management practices (BMPs) arrangement of B M P s and location of sampling points, 217/ polyacrylamide (PAM), 219 reducing runoff output and pesticide load, 216, 219-220 sediment removal by BMPs, 222, 224-225 sediment trap, pond and basins, 220 vegetative strip, 220 See also Pesticide runoff Bifenthrin concentration in surface soils from nursery, 223/ L C values for red and imported fire ant(RIFA) control, 216/ quantification method, 221 red and imported fire ant (RIFA) infestation, 214-215 reduction in runoff, 227/ reduction in runoff along runoff path, 226/ runoff constituent, 215 Big bluestem, pendimethalin recovery from soil vegetated with, 164-165 Bioavailability earthworm test, 162 lettuce seedling test, 163 5 0

pendimethalin by earthworm uptake and lettuce seedling growth, 164/ pesticide residues, 162-163 Biodegradability, carbamate pesticides, 80, 82 Biodégradation lower s-triazine pathway, 132/ photolysis products of 3,5,6trichloro-2-pyridinol (TCP), 20, 23 upper s-triazine pathway, 131/ 1,1 -Bis(p-chlorophenyl)-2,2,2trichloroethane (DDT), aqueous solubility as function of surfactant concentration, 235 Boron-doped diamond (BDD) electrodes, 103-104 See also Triclosan

California Department of Pesticide Regulation (CDPR), nursery runoff, 214 Cannizzaro reactions advantages, 92 disproportionation for 0 phthalaldehyde (ΟΡΑ) neutralization, 89, 9 0 / final product in ΟΡΑ neutralization, 93/ mechanism from H P L C / M S results, 93/ possible routes of ΟΡΑ neutralization, 9 1 / stepwise mechanism, 9 2 / Carbamate pesticides biodegradability, 80, 82 hydroxyl radical reaction rate constants, 8 1 / Carbaryl anodic Fenton treatment (AFT), 77, 79/ structure, 68/ Carbofuran, structure, 68/

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252 Carbon tetrachloride, reduction, 184— 185 Catabolic genes, atrazine, in environment, 136 Cellobiose dehydrogenase (CDH) direct and mediated oxidation and reduction reactions, If lignin degradation, 6, 8 See also White-rot fungi Cetyltrimethylammonium bromide (CTAB), effects on soil water pressure-saturation relationships, 241-242 Chemical vapor deposition, borondoped diamond (BDD) electrodes, 103-104 Chemical warfare agents, destruction, 191, 192 Chloracetamide compounds alachlor, acetochlor, and metolachlor, 200, 201/ degradation in soil, 200 structures of alachlor metabolites, 202/ See also Acetochlor; Alachlor; Metolachlor Chlorinated aliphatic hydrocarbons (CAHs), structure, 182 5-Chloro-2-(2,4-dichlorophenoxy)phenol. See Triclosan 2-Chloro-4-ethylamino-6isopropylamino-s-triazine. See Atrazine 2-Chloro-4-hydroxy-6-amino-2atrazine, dechlorination, 42 Chloroacetanilide, disappearance in thiosulfate solutions, 58/ Chlorofluorocarbons (CFCs), remediation, 190 Chloropicrin bacterial E C values before and after reaction with thiosulfate salts, 60/ half-lives with and without ammonium thiosulfate, 59/ partial replacement for methyl bromide, 170 5 0

reaction rate constant and regression coefficient, 55/ Chlorpyrifos degradation, 16 L C values for red and imported fire ant (RIFA) control, 216/ See also 3,5,6-Trichloro-2-pyridinol (TCP) CIDEX® ΟΡΑ solution. See oPhthalaldehyde (ΟΡΑ) Clavibacter strain, atrazine-degrading, 146-147 Competitive kinetics anodic Fenton treatment (AFT), 77, 80 hydroxyl radical reaction rate constants, 81/ Compound parabolic collectors (CPCs), solar photocatalysis, 117 Contamination. See Phytoremediation; Remediation Cyanuric acid atrazine metabolism to, 40-42 enzymatic hydrolysis, 40/ 5 0

D 2,4-D anodic Fenton treatment (AFT), 72, 74 degradation with different delivery rates of Fenton reagent, 75/ structure, 68/ Dakin reaction aromatic aldehydes, 94 electron-donating groups, 95/ example, 94/ oxidation of aromatic aldehydes, 93 requirements, 95 Dechlorination activity of different metals and halides during solvated electron, 188/ aromatic hydrocarbons, 184 chlorinated organics, 182-183

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253 2-chloro-4-hydroxy-6-amino-striazine (CAOT), 42 dissociative electron transfer, 184, 185 efficiencies of N a and Ca, 186-187 excess water, 185-187 halogenated organic compounds, 52 hydrogen generation, 186 minimum Na for complete, 186, 187/ reduction of carbon tetrachloride, 184-185 transfer of solvated electron to chlorinated aliphatic hydrocarbon, 184 See also Remediation Defluorination, aliphatic fluoro compounds, 192-193 Degradation lignin, 4-5 microbial, of organophosphates, 2728 pentachlorophenol (PCP), 8-10 trichloroethylene, 11 trinitrotoluene (TNT), 10, 12/ See also Anodic Fenton treatment (AFT); 3,5,6-Trichloro-2-pyridinol (TCP); White-rot fungi Dehalogenation activity of metals and halides during solvated electron, 188/ aerobic, of hydrocarbons by whiterot fungi, 12/ reaction between alachlor and thiosulfate salts, 57/ trichloroethylene, 11 Deoxyribonucleic acid (DNA) shuffling, directed evolution, 32-33 Detoxification halogenated organic compounds (HOC), 59-60 pentachlorophenol (PCP), 8-10 solar, of pesticides, 118-123 trinitrotoluene (TNT), 10, 12/

See also Halogenated organic compounds (HOC); Organophosphates; Phytoremediation; White-rot fungi Dextran, o-phthalaldehyde (ΟΡΑ) neutralization, 88 Diazinon anodic Fenton treatment (AFT), 74 LC50 values for red and imported fire ant (RIFA) control, 216/ structure, 68/ variation of oxidation rate parameter and electrolysis current efficiency with N a C l concentration, 76/ 1.2-Dichlorobenzene, structure, 182 1.3- Dichloropropene (1,3-D) bacterial E C values before and after reaction with thiosulfate salts, 60/ concentration in soil gas, 174/ fumigant dissipation rate, 177/ half-lives with and without ammonium thiosulfate, 59/ mass remaining in replicate mesocosms after ammonium thiosulfate/water, 176/ partial replacement for methyl bromide, 170 reaction rate constant and regression coefficient, 55/ Dioxacarb, structure, 68/ Dioxins N a / N H treatment, 188/ structure, 182 Directed evolution, D N A shuffling, 32-33 Disappearance, pesticides, 119-121 Disposal methods, organophosphate compounds, 26 Disposal problems, triclosan, 100-101 Dissipation model, first-order for halogenated fumigants, 176 Diuron, disappearance and mineralization, 120/ D N A shuffling, directed evolution, 32-33 5 0

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Ε Earthworm assay bioavailability, 162 bioavailability of pendimethalin, 164/ Electrochemical oxidation hydroxyl radicals, 102-103 organic compounds, 101-103 See also Triclosan Electrodes, boron-doped diamond (BDD), 103-104 Emissions-reduction strategies, fumigants, 171 Environmental pollution, global problem, 4 Environmental Protection Agency (EPA), Toxics Release Inventory, 195 Escherichia coli atrazine-degrading, 147 expressing organophosphorus hydrolase (ΟΡΗ) and cellulosebinding domain (CBD), 31 Ethylene thiourea (ETU) anodic Fenton treatment (AFT), 70 degradation products, 71/ structure, 71/ Explosives, remediation of soil, 192/

F Fenobucarb, structure, 68/ Fenoxycarb, L C values for red and imported fire ant (RIFA) control, 216/ Fenton processes, production of OH radicals, 115 Fenton treatment method reaction, 66 See also Anodic Fenton treatment (AFT) Ferricyanide, detoxification, 10, 12/ Flow-through reactor, triclosan oxidation, 108-111 5 0

Fumigant emissions reduction, methyl bromide, 60-61 Fumigants air quality, 170 concentration of propargyl bromide and cis-1,3-dichloropropene (1,3D) in soil gas, 174/ concentrations in root zone, 173 concrete mesocosms, 171 decrease in propargyl bromide and methyl isothiocyanate (MITC) in root zone with time, 178/ degradation at soil surface, 170 depletion in root zone by ammonium thiosulfate (ATS) application, 173, 176-177 detoxifying halogenated, 170 dimensions of mesocosms, 172/ emissions-reduction strategies, 171 first-order dissipation model, 176 initial soil gas concentrations, 173 location of soil gas samplers in xy plane, 172/ mass remaining in replicate mesocosms after ATS/water application, 176/ methods, 171,173 methyl bromide (MeBr), 170 normalized soil gas concentrations for propargyl bromide in mesocosm, 175/ properties, 170 rate of fumigant dissipation, 177/ soil gas concentration measurements, 171,173 subsurface application, 177

G Genes, atrazine catabolic, in environment, 136 Glycine, o-phthalaldehyde (ΟΡΑ) neutralization, 86-87 Green neutralization, ophthaialdehyde (ΟΡΑ), 88

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H Halogenated organic compounds (HOC) advantages of thiosulfate salts, 53 alachlor transformation, 56/ application examples, 60-62 bacterial EC50 values of fumigants and herbicides, 60/ dehalogenation reaction between alachlor and thiosulfate, 57/ detoxification, 59-60 disappearance of chloroacetanilide herbicides in thiosulfate, 58/ dissipation of alachlor in aqueous solutions, 55/ dissipation of fumigants in thiosulfate solutions, 54/ effect of ammonium thiosulfate on alachlor and propachlor leaching, 63/ enhanced transformation in soil, 5859 fumigant emissions reduction, 6061 half-lives of fumigants with and without ammonium thiosulfate (ATS), 59/ propargyl bromide transformation, 56/ reaction pathways, 55, 57 reaction rate constants and regression coefficient of fumigants and A T S , 55/ reaction routes, 52-53 relative reactivity, 57, 58/ remediation in ground water and polluted soil, 52 soil remediation, 61-62 thiosulfate salts to dehalogenate HOCs, 53 transformation kinetics in solution, 53-54 uses, 52 Herbicides

adjuvants, 232 extraction method for dégradâtes, 205 materials and methods, 204-205 metabolites in aquifers, 200, 203 relative reactivity, 57, 58/ toxicological properties, 203 See also s-Triazine herbicides Hexachlorobenzene (HCB) aqueous solubility as function of surfactant concentration, 235 effect of surfactant on H C B sorption, 240/ N a / N H treatment, 189 phase distribution of H C B in surfactant-Appling soil system, 241/ History, s-triazine herbicide, 39-40 Hospital instrument processing, ophthalaldehyde (ΟΡΑ) solution, 86 Hydramethylnon, L C values for red and imported fire ant (RIFA) control, 216/ Hydrogen peroxide Dakin reaction, 93-95 ideal neutralization of ophthalaldehyde (ΟΡΑ), 96/ neutralization by oxidation, 9 3 96 ΟΡΑ neutralization, 94/ Hydrolytic attack, bacterial degradation of atrazine, 143, 146 Hydrophile-lipophile balance (HLB), definition, 233 Hydrophobic organic compound (HOC). See Surfactant adjuvants Hydroxyatrazine generation, 41 metabolism by hydroxyatrazine amidohydrolase, 42 Hydroxyl radicals Fenton reagent, 115 production in advanced oxidation processes (AOP), 114-115 Hydrogen, generation, 186 3

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See also White-rot fungi Lindane, structure, 181 Ice-nucleation protein (INP), surface expression, 30-31 Imidacloprid, disappearance and mineralization, 120/ 121 Immobilization, organophosphorus hydrolase (ΟΡΗ), by affinity tags, 28-29 Industrial wastewater designing treatment plan for, 122123 effect of sodium chloride on TCP removal, 19/ solar detoxification, 118 treatment of 3,5,6-trichloro-2pyridinol (TCP)-containing, 18, 20 Iodomethane, soil fumigant, 170

M

Magnetic capture hybridization (MCH), soil mineralizing atrazine, 149-150 Malathion, LC50 values for red and importedfireant (RIFA) control, 216/ Mechanism, Cannizzaro reaction, 92/ 93/ Membrane anodic Fenton treatment (AFT) advance in AFT, 77 apparatus, 78/ changes in degradation rate for carbaryl and electrolysis voltage with NaCl concentration, 79/ Mesocosms Κ dimensions, 172/ fumigants, 171 Kinetic model, anodic Fenton Metabolism treatment (AFT), 72, 74 atrazine to cyanuric acid, 40-42 Kinetics, anodic Fenton treatment s-triazine herbicide, 39-40 (AFT), 77, 80 3,5,6-trichloro-2-pyridinol (TCP), 18, 19/ Methylation, pentachlorophenol (PCP), 8, 9/ Methyl bromide Laccase bacterial EC50 values before and after direct and mediated oxidation and reaction with thiosulfate salts, reduction reactions, 7/ 60/ one electron oxidation, 6 fumigant emission reduction, 60-61 See also White-rot fungi half-lives with and without Langmuir-Hinselwood, kinetic model, ammonium thiosulfate, 59/ 119 reaction rate constant and regression Leachate, pesticide recovery in, during coefficient, 55/ phytoremediation, 161, 162/ Methyl iodide Lettuce seedling bacterial E C values before and after bioavailability, 163 reaction with thiosulfate salts, 60/ bioavailability of pendimethalin, dissipation in thiosulfate, 54/ 164/ half-lives with and without Lignin ammonium thiosulfate, 59/ degradation by white-rot fungi, 4-5 5 0

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257 reaction rate constant and regression coefficient, 55/ Methyl isothiocyanate (MITC) decrease in root zone with time, 178/ fumigant dissipation rate, 177/ mass remaining in replicate mesocosms after ammonium thiosulfate/water, 176/ partial replacement for methyl bromide, 170 Metolachlor chemical structures, 201/ concentration after 250 days remediation, 159/ focus in phytoremediation, 156 movement within soil column during phytoremediation, 161, 162/ percentage of applied with mulberry trees as vegetation, 160, 161/ replacing alachlor, 200 Micellar solubilization aqueous solubility of l,l-bis(pehlorophenyl)-2,2,2trichloroethane (DDT) and hexachlorobenzene (HCB), 235 change in surfactant monomer and micelle mass fraction vs. total surfactant concentration, 234/ critical micelle concentration (CMC), 234 effect of surfactants on hydrophobic organic compound (HOC) solubility, 236 surfactant micelles, 234-235 weight solubilization ratio (WSR), 235-236 See also Surfactant adjuvants Microbial degradation organophosphates, 27-28 s-triazines, 130-136 See also Atrazine Microorganisms, atrazine-degrading, 144/, 145/ Microtox® assay reaction products of triclosan, 109, 111

toxicity of triclosan solutions, 104105 Mineralization atrazine, 136, 146, 206 pesticides, 119-121 Mirex, structure, 181 Mitigation. See Pesticide runoff Model first-order dissipation, for halogenated fumigants, 176 kinetic, of anodic Fenton treatment (AFT), 72, 74 Most probable number (MPN) methodology atrazine-degraders, 132-133 bioremediating bacteria in soils, 149150 Mulberry trees phytoremediation potential, 160, 161/ See also Phytoremediation

Ν Neurotoxins. See Organophosphates Neutralization. See o-Phthalaldehyde (ΟΡΑ) Nitrogen heterocyclic compounds, exposure of living cells, 38 Nocardioides CI90, atrazinedegrading, 148 Non-concentrating solar collectors, solar photocatalysis, 117 Non-halogenated molecules, reductive remediation, 190-191 Nursery production bifenthrin against red and imported fire ant (RIFA), 214-215 industry, 214 mid-size commercial nursery as field site, 214 pesticide fate and safety, 215 pyrethroid insecticides, bifenthrin and permethrin, 215 See also Pesticide runoff

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258 Ο

Ρ

Organophosphates crystal structure of organophosphorus hydrolase (ΟΡΗ), 32 directed evolution, 32-33 disposal methods, 26 D N A shuffling, 32-33 enzyme detoxification, 28-33 genetically engineered Escherichia coli cell, 31 ice-nucleation protein (INP), 30-31 kinetic properties of organophosphorus hydrolase (ΟΡΗ), 27/ microbial degradation, 27-28 modifications of specificity and activity, 31-33 neurotoxins, 26 ΟΡΗ description, 27 ΟΡΗ immobilization by affinity tags, 28-29 site-directed mutagenesis, 31-32 surface expression of ΟΡΗ, 30-31 toxicity and usage, 26 truncated ice-nucleation protein (INPNC),31 whole cell detoxification of OP neurotoxins, 29-30 Organophosphorus hydrolase (ΟΡΗ) crystal structures, 32 description, 27 immobilization by affinity tags, 2829 kinetic properties, 27/ site-directed mutagenesis, 31-32 surface expression of ΟΡΗ, 30-31 Oxidation aldehydes, 89 pentachlorophenol (PCP), 9f See also Hydrogen peroxide; oPhthalaldehyde (ΟΡΑ) Oxidative attack, bacterial degradation of atrazine, 142-143

Pendimethalin bioavailability, 163, 164/ concentration after 250 days remediation, 159/ focus in phytoremediation, 156 percentage remaining in soil with and without vegetation, 158/ recovery in soil vegetated with switchgrass, big bluestem, and prairie grass mixture, 165/ See also Phytoremediation Pentachlorophenol (PCP) cycle of oxidative, reductive, and methylation reactions, 9 / detoxification and degradation, 810 methylation of PCP, 9 / structure, 182 See also White-rot fungi Permethrin concentration in surface soils from nursery, 223/ quantification method, 221 reduction in runoff, 227/ reduction in runoff along runoff path, 228/ runoff constituent, 215 Peroxidases direct and mediated oxidation and reduction reactions, If lignin degradation, 5-6 See also White-rot fungi Peroxide. See Hydrogen peroxide Persistent organic compounds, classification, 114 Pesticide residues, bioavailability, 162-163 Pesticide runoff arrangement of best management practices (BMPs) and location of sampling points, 217/ best management practices (BMPs), 216,219-220

Gan et al.; Pesticide Decontamination and Detoxification ACS Symposium Series; American Chemical Society: Washington, DC, 2003.

259 bifenthrin against red and imported fire ant (RIFA) infestation, 214215 concentrations of bifenthrin and permethrin in surface soils, 223/ experimental, 215-221 L C values of insecticides for control of RIFA, 216/ locations for surface soil sampling at nursery site, 218/ monthly runoff output, 219/ nursery production for pesticide fate and safety, 215 percentages of reduction in sediment level in runoff water, 225/ pesticide removal by B M P s , 225226,228-229 polyacrylamide (PAM) for improving, 219 reduction in bifenthrin in runoff at different locations, 227/ reduction in bifenthrin level in runoff along runoff path, 226/ reduction in permethrin in runoff along runoff path, 228/ reduction in permethrin in runoff at different locations, 227/ reduction in suspended solid content of runoff, 224/ sampling and analysis, 220-221 sediment removal by BMPs, 222, 224-225 sediment trap, pond and basins slowing down runoff flow, 220 site characterization and survey for pesticide sources, 215-216 sources of pesticides in nursery runoff, 221-222 vegetative strip, 220 Pesticides agriculture, 114 dechlorination, 182-183 destruction methods, 182 disappearance and mineralization, 120/

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fate of radio-labeled, within prairie grass-soil system, 163-164 future for photocatalysis, 123-124 kinetic model, 119 modern agriculture, 26 movement within soil column during phytoremediation, 161, 162/ nitrogen heterocyclic, 38/ persistent organic compound classification, 114 perspective, 195-196 remediation, 189 solar detoxification, 118-123 structures, 181-182 water contaminants, 66 See also Anodic Fenton treatment (AFT); Halogenated organic compounds (HOC); Organophosphates Phanerochaete chrysosporium. See White-rot fungi Photocatalysis compound parabolic collectors (CPCs), 117 detoxication by solar, 115 future outlook for pesticides, 123124 laboratory research, 116-118 non-concentrating solar collectors, 117 pilot plant scheme, 116/ schematic of CPCs, 117/ Photodegradation proposed pathway for 3,5,6-trichloro2-pyridinol (TCP), 22/ TCP, 20 TCP experiments, 17 TCP upon exposure to ultraviolet (UV) light, 2 1 / o-Phthalaldehyde (ΟΡΑ) advantages of Cannizzaro reactions, 92 advantages of CIDEX® ΟΡΑ solution, 86 ammonia precipitating ΟΡΑ, 88

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260 Cannizzaro final product by G C / M S , 93/ Cannizzaro mechanism by H P L C / M S results, 9 3 / Cannizzaro reaction for neutralization by sodium hydroxide, 89, 92 Dakin reaction, 93-95 hospital instrument processing, 86 ideal green method, 88 ideal neutralization by hydrogen peroxide, 9 6 / neutralization by glycine, 86-87 neutralization by scavenging on dextran, 88 neutralization by scavenging on silica support, 87 neutralization by sodium bisulfite, 86 neutralization with hydrogen peroxide by oxidation, 93-96 possible neutralization products by redox or disproportionation reactions, 9 0 / possible routes for Cannizzaro reactions, 9 1 / reduction by sodium borohydride, 87 starch support, 88 stepwise mechanism of Cannizzaro reactions, 9 2 / Phylogenetics, atrazine metabolizing bacteria, 135-136 Phytoremediation bioavailability of pendimethalin, 163 bioavailability of pesticide residues, 162-163 concentration of metolachlor and pendimethalin after 250 days, 159/ considerations, 165-166 definition, 156 diversity, 156 earthworm bioavailability assay, 162 evaluating role of species type and mixture, 164-165 evaluating success using alternative endpoints, 160-163

fate of radio-labeled pesticides within prairie grass-soil systems, 163-164 lettuce seedling bioavailability assay, 163 mulberry trees, 160 percentage of applied atrazine, metolachlor, and pendimethalin recovered from columns, 161/ percentage of metolachlor recovered in leachate, 162/ percentage of pendimethalin and trifluralin remaining for vegetated and unvegetated, 158/ pesticide movement within soil column during, 161 pesticides in focus, 156 plants of interest, 156-157 potential for point-source pesticide contamination, 156 prairie grasses in column study, 158159 prairie grasses in microplot study, 157-158 recovered pendimethalin in big bluestem, switchgrass, and mixed prairie grasses, 165/ techniques, understanding and improving, 163-165 Plasma membrane redox potential, metabolism of chemicals, 10, 12/ Pollution, global problem, 4 Polyacrylamide ( P A M ) , reducing runoff, 219 Polychlorinated biphenyls (PCBs) destruction in oils using N a / N H , 189/ destruction in soils using N a / N H or Ca/NH ,183t incineration, 182 N a / N H treatment, 188/ structure, 181, 182 Polynuclear aromatic hydrocarbon (PNAs), reductive remediation, 190-191 Pond, slowing runoff flow, 220 3

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261 Prairie grasses column study of phytoremediation, 158-159 fate of radio-labeled pesticides within prairie grass-soil system, 163-164 microplot phytoremediation study, 157-158 pendimethalin recovery from soil vegetated with, 164-165 See also Phytoremediation Promecarb, structure, 68/ Propachlor effect of ammonium thiosulfate on leaching, 6 3 / relative reactivity, 57, 58/ Propargyl bromide bacterial E C values before and after reaction with thiosulfate salts, 60/ concentration in soil gas, 174/ decrease in root zone with time, 178/ dissipation in thiosulfate, 54/ fumigant dissipation rate, 177/ half-lives with and without ammonium thiosulfate (ATS), 59/ mass remaining in replicate mesocosms after ATS/water, 176/ normalized soil gas concentrations, 175/ reaction rate constant and regression coefficient, 55/ soil fumigant, 170 transformation, 56/ Pseudaminobacter CI47, atrazinedegrading, 148 Pseudomonas species atrazine-degrading, 146-148 expression of atzB as function of medium pH, 151/ metabolism of 3,5,6-trichloro-2pyridinol (TCP) by resting cells, 19/ TCP-degrading, 17-18 Pyriproxyfen, L C values for red and imported fire ant (RIFA) control, 216i 5 0

5 0

Q Quinones, detoxification, 10, 12/

R Radio-labeled pesticides, fate within prairie grass-soil system, 163164 Reaction pathways, halogenated organic compounds with thiosulfate salts, 55, 57 Reactivity, herbicides, 57, 58/ Red and imported fire ant (RIFA) infestation, bifenthrin, 214-215 Reduction destruction of polychlorinated biphenyls (PCBs), 183/ nitro- and nitrate containing organic compounds, 191 pentachlorophenol (PCP), 9 / polychlorinated biphenyls (PCBs), 182 sodium borohydride, 87 solvated electrons, 183 Reductive dechlorination, halogenated organic compounds, 52-53 Remediation CH3CCI3 soils, 194/ chlorofluorocarbons (CFCs), 190 defluorination of aliphatic fluoro compounds, 192-193 destruction of chemical warfare agents, 191, 192/ destruction of polychlorinated biphenyls (PCBs), 189/ Na consumption vs. concentration of chlorinated contaminant in soil, 193-195 N a / N H treatment, 188/ pesticide-contaminated soils using Na/NHa in mobile unit, 190/ pesticides, 189 polynuclear aromatic hydrocarbons (PNAs), 190-191 3

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262 reductive, of nonhalogenated molecules, 190-191 sodium consumption vs. concentration, 193-195 soil, with thiosulfate salts, 61-62 tetrachloroethylene-contaminated soils, 194/ See also Phytoremediation Root zone decrease of propargyl bromide and methyl isothiocyanate (MITC) with time, 178/ fumigant depletion, 173, 176-177 See also Fumigants Runoff. See Pesticide runoff

S Sediment trap, slowing runoff flow, 220 Silica support, o-phthalaldehyde (ΟΡΑ), 87 Site-directed mutagenesis, organophosphorus hydrolase (ΟΡΗ), 31-32 Sodium bisulfite, o-phthalaldehyde (ΟΡΑ) neutralization, 86 Sodium borohydride, reduction reaction, 87 Sodium chloride effect of concentration on 3,5,6trichloro-2-pyridinol (TCP) removal, 19/ industrial wastewater treatment, 18, 20 Sodium consumption, factors affecting, 193-195 Sodium hydroxide, o-phthalaldehyde (ΟΡΑ) neutralization, 89, 91/ 92 Sodium ions. See Solvated electrons Soil abundance of atrazine degrading bacteria, 135/ atrazine degradation, 132-134

destruction of polychlorinated biphenyls (PCBs), 183/ enhanced transformation, 58-59 hydrolytic attack for bacterial degradation of atrazine, 143, 146 monitoring abundance and activity of bioremediating bacteria, 149-150 oxidative attack of atrazine, 142-143 PCR-denaturing gradient gel electrophoresis (DGGE), 137/ remediation of contaminated with explosives, 192/ remediation of pesticidecontaminated, 190/ surfactant sorption, 237-238 See also Atrazine; Surfactant adjuvants Soil column, pesticide movement within, during phytoremediation, 161,162/ Soil gas concentrations at root zone, 173 initial concentrations, 173 measuring concentrations, 173 See also Fumigants Soil remediation thiosulfate salts, 61-62 See also Phytoremediation Soil water retention relationships, van Genuchten (VG) equation, 242 Solar collectors, photocatalysis, 117 Solar detoxification commercial pesticides, 121-123 disappearance and mineralization of commercial pesticides, 122/ disappearance of pesticides, 120/ equation describing kinetics, 119 future outlook, 123-124 imidacloprid and formulation, 121 mineralization of pesticides, 120/ photocatalytic disappearance with Ti0 , 119, 121 pure pesticides, 119, 121 treatment of industrial wastewater, 118-119 2

Gan et al.; Pesticide Decontamination and Detoxification ACS Symposium Series; American Chemical Society: Washington, DC, 2003.

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263 treatment plant for wastewaters, 122— 123 Solar photocatalysis, detoxication, 115 Solvated electrons activity of metals and halides during solvated electron dechlorinations, 188/ Na or Ca for reductions, 183 Specificity directed evolution, 32-33 site-directed mutagenesis, 31-32 Starch supports, o-phthalaldehyde (ΟΡΑ) neutralization, 88 Surface and aquifer sediments alachlor mineralization, 206 alachlor under aerobic and anaerobic conditions, 206, 208/ atrazine mineralization, 206 materials and methods, 204-205 metabolites of alachlor under aerobic and anaerobic conditions, 206, 210 organic carbon content and partition coefficients of atrazine and alachlor, 207/ physical and chemical characteristics, 205-206 relative mobility (Rf value), 205, 209/ sorption and degradation of alachlor, 210 Surfactant adjuvants apparent soil-water distribution coefficient ( K * ) , 239-240 aqueous solubility of l,l-bis(pchlorophenyl)-2,2,2trichloroethane (DDT) and hexachlorobenzene (HCB) vs. Triton X-100 concentration, 235/ cetyltrimethylammonium bromide (CTAB) and soil water pressuresaturation relationships, 241-242 change in surfactant monomer and micelle mass fraction vs. total surfactant concentration, 234/ D

coupled hydrophobic organic compound (HOC) and surfactant sorption, 238-240 critical micelle concentration (CMC), 234 effect of Tween 80 on H C B sorption by Appling soil, 240f effects of surfactant-induced changes on surface tension and contact angle, 242 effects of surfactants on H O C solubility, 236 effects of surfactants on soil water retention and flow, 241-243 herbicide formulations, 232 H O C phase distribution in surfactantsoil systems, 236-240 hydrophile-lipophile balance (HLB), 233 impact on water flow and coupled transport, 242-243 influence of Triton X-100 pulse injection on soil water pressure in unsaturated column, 244/ Langmuir sorption parameters for surfactant-soil systems, 238/ measured and fitted soil water retention curves for F-70 Ottawa sand, 243/ micellar solubilization, 233-236 phase distribution of H C B in Tween 80-Appling soil system, 241/ properties of representative nonionic surfactants as pesticide adjuvants, 233/ schematic of three-phase soil system, 237/ soil water retention (pressuresaturation) relationships, 242 surfactant properties, 232-233 surfactant sorption, 237-238 van Genuchten (VG) equation, 242 weight solubilization rate (WSR), 235-236 Switchgrass, pendimethalin recovery from soil vegetated with, 164-165

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264

Tags, affinity, organophosphorus hydrolase (ΟΡΗ) immobilization, 28-29 Tetrachloroethylene, structure, 182 Thiosulfate salts advantages, 53 bacterial E C values of herbicides before and after reaction with, 60/ dehalogation of halogenated organic compounds (HOC), 53 dehalogenation reaction between alachlor and, 57/ dissipation of fumigants in, 54/ enhanced transformation in soil, 5859 fumigant emissions reduction, 60-61 soil remediation, 61-62 transformation of HOCs, 53-54 See also Halogenated organic compounds (HOC) Toxicity Microtox® assay for triclosan, 104105 triclosan, 109, 111 Toxics Release Inventory, pesticides, 195 s-Triazine herbicides atrazine, 42-43 atrazine chlorohydrolase gene, 44 atrazine metabolism to cyanuric acid, 40-42 atzA catalyzing dehalogenation, 45 atzD, atzE, and atzF genes, 43 2-chloro-4-hydroxy-6-amino-striazine (CAOT), 42 commercially relevant nitrogen heterocyclic pesticides, 38/ enzymatic hydrolysis of cyanuric acid, 40/ evolution of metabolic pathway for atrazine, 42-45 fate, 39 history, 39-40 hydroxyatrazine metabolism, 42

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5 0

N-isopropylammelide isopropylaminohydrolase (AtzC), 42 laboratory experiments emulating evolutionary pathway between triA and atzA, 44-45 metabolism, 39-40 metabolism of atrazine in Pseudomonas sp. ADP, 41/ microbial degradation, 130-136 origins of atzA, atzB, and atzC genes, 43 success, 38-39 weed control, 130 See also Atrazine 3,5,6-Trichloro-2-pyridinol (TCP) biodégradation of TCP photolysis products, 20, 23 degradation metabolite, 16 effect of sodium chloride concentration on TCP removal, 19/ enrichment culture techniques, 16-17 experimental,-16-17 isolation and characterization of TCP-degrading bacteria, 17-18 metabolism by resting cells of Pseudomonas sp., 19/ photodegradation, 20 photodegradation experiments, 17 photodegradation upon exposure to UV light, 21/ proposed photodegradation pathway, 22/ treatment of TCP-containing industrial wastewater, 18, 20 Trichloroethylene dehalogenation and degradation, 11 See also White-rot fungi Triclopyr degradation, 16 See also 3,5,6-Trichloro-2-pyridinol (TCP) Triclosan batch experiments, 104 batch reactor, 105-108

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265 boron-doped diamond (BDD) electrodes, 103-104 concentrations as function of electrolysis time, 106, 107/ cyclic voltammetry scans with B D D electrode, 105/ disposal problems, 100-101 effluent concentrations from flowthrough reactor, 109/ electrochemical oxidation, 101103 experiments in DiaCell® silicon substrate (CSEM) flow-through reactor, 104 flow-through reactor, 108-111 galvanostatic electrolysis at anodic current densities of 5 and 15 mA/cm , 107/ major byproducts of electrolysis, 110/ materials and methods, 104-105 Microtox® assay, 104-105 Microtox® E C values of reaction products, 109, 111 normalized toxicity and concentrations during electrolysis, 111/ oxidation by hydroxyl radicals, 102103 removal rates at current densities of 5 and 15 mA/cm ,106,108 structure, 100/ uses, 100 Trifluralin focus in phytoremediation, 156 percentage of applied with mulberry trees as vegetation, 160, 161/ percentage remaining in soil with and without vegetation, 158/ See also Phytoremediation Trinitrotoluene (TNT) detoxification and degradation, 10, 12/ See also White-rot fungi Truncated ice nucleation protein (INPNC), surface expression, 31 2

5 0

2

V van Genuchten (VG) equation, soil water retention relationships, 242 Vegetation role of species type and mixture in phytoremediation, 164-165 See also Phytoremediation Vegetative strip, slowing runoff flow, 220 Vibriofisheri,acute toxicity test, 59

W

Wastewater designing treatment plan for, 122123 effect of sodium chloride on 3,5,6trichloro-2-pyridinol (TCP) removal, 19/ treatment of TCP-containing, 18, 20 Water, oxidative attack of atrazine, 142-143 Weight solubilization ratio (WSR), definition, 235-236 Wetland systems, atrazine degradation, 134 White-rot fungi aerobic dehalogenation of hydrocarbons, 12/ cellobiose dehydrogenase, 6, 8 chemicals by fungal plasma membrane redox system, 12/ direct and mediated oxidation and reduction reactions, 7 / laccase, 6 lignin, 4-5 methylation of pentachlorophenol (PCP), 9 / oxidative, reduction, and methylation reactions for PCP degradation, 9/ pentachlorophenol detoxification and degradation, 8-10 peroxidases, 5-6 reaction possibilities, 5-8

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266 Wood-rotting fungi, lignin degradation, 4

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trichloroethylene dehalogenation and degradation, 11 trinitrotoluene (TNT) detoxification and degradation, 10

Gan et al.; Pesticide Decontamination and Detoxification ACS Symposium Series; American Chemical Society: Washington, DC, 2003.