UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON, D.C. 20460 ENVIRONMENTAL FATE AND EFFECTS DIVISION OFFICE OF PESTICIDE PROGRAMS June 8, 2000 SUBJECT: Reregistration of sodium acifluorfen (PC Code 114402 / Company: 007969 BASF Corporation) for uses on soybeans, peanuts and rice (D252561). FROM: James J. Goodyear, Ph.D. Biologist (7507C) James Wolf, Ph.D. Environmental Scientist Environmental Risk Branch III/EFED THRU: Daniel Rieder, Branch Chief (7507C) Environmental Risk Branch III/EFED TO: Betty Shackleford: Branch Chief (7508C) Christina Scheltema: Chemical Review Manager Reregistration Branch III/SRRD SUMMARY Attached is EFED’s ecological risk assessment and drinking water assessment for sodium acifluorfen. The present review considers: peanuts, soybeans and rice. Lawn uses are for spot treatment and are considered a minimal risk. In addition to being a registered herbicide, acifluorfen is also the primary degradate of the herbicide lactofen (Chemical Code 128888). Acifluorfen accounted for approximately 52 percent of the applied lactofen in an aerobic metabolism soil study. Sodium acifluorfen and lactofen also both share the common degradate amino acifluorfen. This memo highlights EFED’s concerns and provides suggestions for product labeling. It also identifies data requirements to reduce uncertainties in the assessment. DATA REQUIREMENTS Environmental Fate Data Requirements: Even though all guideline data requirements have been fulfilled, the characterization of the environmental fate of acifluorfen and the other degradates may not be as straight forward as would be indicated by the basic fate properties (e.g., half-life and Koc). Thus, our ability to predict the fate or concentrations of acifluorfen in soil or water has considerable uncertainty. Additional studies are needed to better define the variability of the persistence and mobility of acifluorfen, amino acifluorfen, and desnitroacifluorfen and what site factors may be able to better predict behavior of the acifluorfen residues in the environment. A simple example of can be made if one looks at the persistence and mobility of acifluorfen. The aerobic soil metabolism half-live values of acifluorfen generally range between 100 and 200 days, it is stable to hydrolysis, it does not readily photo-degrade and it is mobile (Kads range between 0.1 and 5.3 mL/g). These fate properties triggered a small-scale prospective ground-water study which occurred in the central sand region of Wisconsin on soybeans. The occurrence of acifluorfen residues in ground water was not unexpected based upon its fate attributes. Although, the frequency (20 percent) and range of detections (1 to 46 µg/L) with a long term average of 7.33 µg/L was not necessarily expected. The prospective study included acifluorfen and two soil and water degradates (amino acifluorfen and desnitroacifluorfen). Neither of the two degradates were detected. A field dissipation half-life of about 15 days was calculated for the disappearance of acifluorfen from the upper 0.2 or 0.3 meters depending upon sampling date (sampling increment varied with time). In this study leaching was the major dissipation pathway of acifluorfen. The occurrence of acifluorfen residues in the soil-pore water and ground water confirmed this pathway. The registrant also conducted a small-scale retrospective ground- water monitoring study at five locations. Soil samples were also collect for acifluorfen analysis. The dissipation half-lives varied from 7 to 66 days depending upon study location and what value was used for initial acifluorfen concentrations. There was no evidence of leaching from soil samples collected and no residues were detected in ground water. Since degradates were not measured it is not possible to determine whether acifluorfen concentrations declined by being leached out of the surface soil, were degraded in place, or were redistributed within the soil profile to levels below the detection limit. Acifluorfen has been included in other ground water and surface water studies. While additional residues have been found, residues are not found at all of the surface or ground water studies or locations. Assuming that these studies were conducted in actual use areas, at hydrologically vulnerable sites, and with sufficient detections limits, the fate data suggest there would be more frequent detections. Monitoring data for the degradates is too limited for any type of assessment. With a pKa of 3.5 (acid dissociation constant), acifluorfen exists in the dissociated anion form in most agricultural soils since the pH of these soils usually exceeds the pKa of the acid. Sodium-acifluorfen dissociates resulting in the negatively charged acifluorfen. Negatively charged sorption sites, such as clay minerals, are therefore expected to have little contribution to the adsorption process. Despite charges that would result in repulsion effects, some acifluorfen is apparently sorbed by soil or soil constituents. The adsorption/desorption of acifluorfen is dependent upon pH, organic carbon content, and ammonium oxalate extractable iron content of the soil (positively charged), but not necessarily the percent of clay but mineral type. Acifluorfen may be sorbed or precipitated by forming complexes with divalent or trivalent cations. Acifluorfen sorption appears to be a non-equilibrium, time- dependent process. Under anaerobic conditions acifluorfen is more rapidly reduced to amino acifluorfen, which may be less mobile (Kads 1.25 to 47.01 sand to loamy sand) depending on soil texture. The Kads from the laboratory studies suggest a higher leaching potential for the parent and variable leaching potential for the amino acifluorfen. The environmental fate studies and published literature suggest that under different conditions the persistence and the mobility may be less than that indicated by most of the laboratory and field (variable field dissipation half-lives, Kads) study data. Additional fate studies should be conducted to determine whether relationships between specific soil and/or environmental conditions could provide information to further refine the exposure assessment. It is recommended that the registrant meet with the Agency to develop an approach to develop the necessary information to address the uncertainties surrounding the fate of acifluorfen. Some or all of the following studies would be useful in reducing some of the uncertainty. Guideline Study Discussion Number There is a need to tie the individual terrestrial and soil fate processes into a comprehensive understanding. Data are necessary to be able to understand the importance of the different processes under different environmental conditions. 163-1 Soil Partition This study is necessary to support the registration Coefficient for of the herbicide. Because the sorption of acifluorfen acifluorfen, amino depends upon a number of soil properties. acifluorfen, and Acifluorfen sorption is also a non-equilibrium, desnitro acifluorfen time-dependent process. The mobility of acifluorfen in soil is affected by the rate as well as the maximum extent of sorption. Amino acifluorfen is highly variable, depending upon soil texture. By better understanding the conditions that influence sorption, management options to prevent water contamination would be easier. This information is also needed for subsoils. 162-1 Aerobic soil The line between metabolic and chemical metabolism degradation of acifluorfen is quite blurry. Acifluorfen also degrades to amino acifluorfen and a number of identified polar substances. The fate of these needs to better characterized. 162-2 Anaerobic soil Acifluorfen is rapidly transformed to amino metabolism acifluorfen. The fate of acifluorfen beyond this point is not clear. Its mobility is quite variable - high to low, with apparent persistence. There is a need to tie the individual studies into a comprehensive understanding to the fate of acifluorfen and degradates under different environmental conditions. 162-3 Anaerobic Aquatic Need to tie into the aerobic conditions better. Metabolism 162-4 Aerobic Aquatic The aerobic aquatic half-life suggest that Metabolism acifluorfen is persistent in an aquatic environment. Aqueous photolysis is quite rapid. 164-1 Terrestrial Field This study may be necessary to relate laboratory Dissipation results to actual field conditions. 164-2 Aquatic Dissipation The rice studies showed rapid degradation of acifluorfen with low concentrations of degradates formed. The importance of aqueous photolysis (e.g., the rice pond was only 4 inches deep) and reducing (anaerobic processes) conditions is unclear in other water bodies. Ecological Effects Data Requirements: Guideline Study Discussion Number 123-1(a) Seedling Emergence The two studies above are required to support the registration of an herbicide. The "value added" is 123-1(b) Vegetative Vigor high, because as an herbicide, acifluorfen is expected to injure plants. Previously submitted studies were consider invalid, because the acifluorfen solution applied to the experimental plants was too dilute and the water may have washed the chemical away from the plant. This caused uncertainty about the exposure. 141-1 Honey Bee Acute Acifluorfen will be applied in the spring by air to Contact major crops such as rice, soybeans, and peanuts, resulting in potential exposure to bees, especially off site. The "value added" would be medium, because acifluorfen is an herbicide and is not applied to a crop in bloom. UNCERTAINTY: Acifluorfen acts through inhibition of Protox (protoporphyrinogen