&EPA United States Environmental Protection Agency Office of Water 4304T EPA 822-R-03-029 December 2003 Ambient Aquatic Water Quality Criteria for Nonylphenol - Draft ------- AMBIENT AQUATIC LIFE WATER QUALITY CRITERIA FOR NONYLPHENOL - DRAFT (CAS Registry Number 84852-15-3) (CAS Registry Number 25154-52-3) U.S. ENVIRONMENTAL PROTECTION AGENCY OFFICE OF WATER OFFICE OF SCIENCE AND TECHNOLOGY HEALTH AND ECOLOGICAL CRITERIA DIVISION WASHINGTON D.C. ------- NOTICES This document has been reviewed by the Health and Ecological Criteria Division, Office of Science and Technology, U.S. Environmental Protection Agency, and is approved for publication. Mention of trade names or commercial products does not constitute endorsement or recommendation for use. This document is available to the public through the National Technical Information Service (NTIS), 5285 Port Royal Road, Springfield, VA 22161. It is also available on EPA's web site: http: //www. epa. gov/waterscience/criteria/nony Iphenol/ ------- FOREWORD Section 304(a)(l) of the Clean Water Act of 1977 (P.L. 95-217) requires the Administrator of the Environmental Protection Agency to publish water quality criteria that accurately reflect the latest scientific knowledge on the kind and extent of all identifiable effects on health and welfare that might be expected from the presence of pollutants in any body of water, including ground water. This document is a revision of previous drafts based upon consideration of comments received from US EPA staff and independent peer reviewers. Criteria contained in this document replace any previously published EPA aquatic life criteria for the same pollutant. The term "water quality criteria" is used in two sections of the Clean Water Act, section 304(a)(l) and section 303(c)(2). The term has a different program impact in each section. In section 304, the term represents a non-regulatory, scientific assessment of ecological effects. Criteria presented in this document are such scientific assessments. If water quality criteria associated with specific stream uses are adopted by a state as water quality standards under section 303, they become enforceable maximum acceptable pollutant concentrations in ambient waters within that state. Water quality criteria adopted in state water quality standards could have the same numerical values as criteria developed under section 304. However, in many situations states might want to adjust water quality criteria developed under section 304 to reflect local environmental conditions and human exposure patterns. Alternatively, states may use different data and assumptions than EPA in deriving numeric criteria that are scientifically defensible and protective of designated uses. It is not until their adoption as part of state water quality standards that criteria become regulatory. Guidelines to assist the states and Indian tribes in modifying the criteria presented in this document are contained in the Water Quality Standards Handbook (U.S. EPA 1994). This handbook and additional guidance on the development of water quality standards and other water-related programs of this agency have been developed by the Office of Water. This draft document is guidance only. It does not establish or affect legal rights or obligations. It does not establish a binding norm and cannot be finally determinative of the issues addressed. Agency decisions in any particular situation will be made by applying the Clean Water Act and EPA regulations on the basis of specific facts presented and scientific information then available. Geoffrey H. Grubbs Director Office of Science and Technology 111 ------- ACKNOWLEDGMENTS Larry T. Brooke (author) University of Wisconsin-Superior Superior, Wisconsin Frank Gostomski (document coordinator) U.S. EPA Health and Ecological Criteria Division Washington, D.C. IV ------- CONTENTS T Page NOTICES ii FOREWORD iii ACKNOWLEDGMENTS iv TABLES vi FIGURES vi Introduction 1 Acute Toxicity To Aquatic Animals 6 Chronic Toxicity To Aquatic Animals 8 Toxicity To Aquatic Plants 11 Bioaccumulation 12 Other Data 13 Unused Data 17 Summary . 17 National Criteria .... 18 Implementation 19 References 52 ------- TABLES 1. Acute Toxicity of Nonylphenol to Aquatic Animals . . . . 24 2a. Chronic Toxicity of Nonylphenol to Aquatic Animals 29 2b. Acute-Chronic Ratios 30 3. Ranked Genus Mean Acute Values with Species Mean Acute-Chronic Ratios 31 4. Toxicity of Nonylphenol to Aquatic Plants 34 5. Bioaccumulation of Nonylphenol by Aquatic Organisms 35 6. Other Data on Effects of Nonylphenol on Aquatic Organisms 38 FIGURES 1. Ranked Summary of Nonylphenol GMAVs - Freshwater 21 2. Ranked Summary of Nonylphenol GMAVs - Saltwater 22 3. Chronic Toxicity of Nonylphenol to Aquatic Animals 23 VI ------- I Introduction1 Nonylphenol (C15H240) is produced from cyclic intermediates in the refinement of petroleum and coal-tar crudes. It is manufactured by alkylating phenol with mixed isomeric nonenes in the presence of an acid catalyst. The product is a mixture of alkylphenols, predominantly para-substituted (4-nonylphenol; CAS No. 104-40-5) and occasionally ortho-substituted (2-nonylphenol; CAS No. 136- 83-4), with various isomeric, branched-chain nonyl (nine carbon) groups. (Commercial mixtures containing specified amounts of nonylphenol isomers and 2,4-dinonylphenol are given specific CAS Numbers, either 25154-52-3 or 84852-15-3. These products were used for deriving the water criteria for nonylphenol.) There is little direct use for nonylphenol except as a mixture with diisobutyl phthalate to color fuel oil for taxation purposes and with acylation to produce oxime as an agent to extract copper. Most nonylphenol is used as an intermediate chemical which, after etherification by condensation with efhylene oxide in the presence of a basic catalyst, produces the nonionic surfactants of the nonylphenol ethoxylate type. The nonionic surfactants are used as oil soluble detergents and emulsifiers that can be sulfonated or phosphorylated to produce anionic detergents, lubricants, antistatic agents, high performance textile scouring agents, emulsifiers for agrichemicals, antioxidants for rubber manufacture, and lubricant oil additives (Reed 1978). Nonylphenol is produced at a high annual tonnage rate. Its production in the U.S. was 147.2 million pounds (66.8 million kg) in 1980 (USITC 1981), 201.2 minion pounds (91.3 million kg) in 1988 (USITC 1989), 230 million pounds (104 million kg) in 1998 (Harvilicz 1999), and demand is increasing about 2 percent annually. Nonylphenol has an approximate molecular weight of 215.0 to 220.4 g/mole, is a pale yellow highly viscous liquid with a slight phenolic odor and a specific gravity of 0.953 g/mL at 20°C (Budavari 1989). It has a dissociation constant (pKa) of 10.7 ±1.0; octanol/water partition coefficient (Log Kow) of 3.80 to 4.77; pH-dependent water solubility of 4,600 fig/L at pH 5.0, 6,237 ^g/L at pH 7, 11,897 ^g/L at pH 9 and 3,630 /ig/L in seawater; soluble in many organic solvents; and has a vapor pressure of 4.55 x 10"3 (±3.54 x 10"3) Pa (Roy F. Weston Inc. 1990). Ahel and Giger (1993) measured the solubility of nonylphenol at different temperatures in distilled water and demonstrated a nearly linear relationship in solubility of 4,600 Mg/L at 2°C to 6,350//g/Lat25°C. 1A comprehension of the "Guidelines for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and their Uses" (Stephen et al. 1985), hereafter referred to as the Guidelines, is necessary to understand the following text, tables and calculations. 1 ------- TT Nonylphenol has been studied for its acute and chronic toxicity to aquatic organisms and results of many studies are well summarized in a review article (Staples et al. 1998). Additionally, this review article addresses the ability of nonylphenol to bioaccumulate in aquatic organisms. Nonylphenol and nonylphenol ethoxylates have been found in the environment and a review of studies describing their distribution has been published (Bennie 1999). Shackelford et al. (1983) reported 4-nonylphenol at average concentrations ranging from 2 to 1,617 ^ig/L in eleven water samples associated with various industrial sources. Bennie et al. (1997) measured water concentrations from 0.01 to 0.92 yug/L in 25 percent of the sites sampled in the Great Lakes. They found nonylphenol in all sediment samples and the concentrations ranged from 0.17 to 72 //g/g (dry weight). Studies have shown the presence of nonylphenol and its ethoxylates in treatment plant wastewaters (Ellis et al. 1982, Giger et al. 1981) and in sewage sludges (Giger et al. 1984). A study was conducted of thirty river reaches in the continental U.S. in 1989 and 1990 to determine the frequency and concentrations of nonylphenol and its ethoxylates in water and sediments. Nonylphenol was found in approximately 30 percent of the water samples and concentrations in water ranged from about 0.20 to 0.64 jug/L. Approximately 71 percent of the sites had measurable concentrations of nonylphenol in the sediments and the concentrations ranged from about 10 to 2,960 jug/kg. Various ethoxylates of nonylphenol were found in 59 to 76 percent of the water samples, varying by extent of ethoxylation (Naylor 1992, Naylor et al. 1992, Radian Corp. 1990). Keith et al. (2001) measured nonylphenol in fish tissues of seven species from the Kalamazoo River and the river's mouth at Lake Michigan. They found 41 percent of the samples had measurable concentrations of nonylphenol with a range of 3.3 to 29.1 ^g/kg, and a mean value of 12.0 Aig/kg. Most nonylphenol enters the environment as 4-alkylphenol polyethoxylate surfactants which are degraded to 4-alkylphenol mono- and diethoxylates in active sewage sludges (Giger et al. 1984). It was theorized by Giger et al. (1984) that further transformation of 4-alkylphenol mono- and diethoxylates to 4-nonylphenol is favored by anaerobic environments. They conducted experiments with stabilized (anaerobic) and raw (aerobic) sewage sludge and found that concentrations of 4- nonylphenol increased four to eight times in the stabilized versus two times in the raw sludge, a finding which supported their theory. Persistence of nonylphenol in sewage effluents and the environment has been studied and a review has been written (Maguire 1999) of published studies. Gaffney (1976) determined that 1 mg/L nonylphenol did not degrade during a 135-hr incubation with domestic wastewater. He also measured ------- IT no change in nonylphenol concentration at 24 hr in industrial wastewater, but after 135 hr there was a 45 percent degradation of the compound. Sundaram and Szeto (1981) studied nonylphenol fate in stream and pond waters when incubated in open and closed containers. They found no degradation of nonylphenol when incubated in open containers of the pond or stream waters and a half-life of 2.5 days, probably due to volatization. After three days of incubation in pond or stream waters in closed containers, a breakdown product was measured and half-lives were estimated of 16.5 and 16.3 days, respectively. The same study demonstrated that nonylphenol in pond water with sediment present resulted in about 50 percent of the nonylphenol appearing in the sediment after 10 days. About 80 percent of the nonylphenol in the sediment was degraded in 70 days. No degradation of nonylphenol occurred when autoclaved water and sediment samples were used. Staples et al. (1999) measured a half-life of 20 days at 22 °C for nonylphenol at a concentration of 31 mg/L. They suggested that the temperature of water and the initial concentration of the nonylphenol both affect the degradation rate of the chemical. Ahel et al. (1994a,b) studied the fate and transport of alkylphenol polyethoxylates (APrcEO) and their metabolites in the Glatt River system in Northern Switzerland from the Greifensee to the Rhine River. Water samples were collected at eight sites along the river hourly and seasonally. They found nonylphenol concentrations to be lower than other metabolites and nonylphenol concentrations were most common in the 1 to 3 //g/L range. Metabolite concentrations of APrcEO's varied with time of day reflecting wastewater treatment plant discharge fluctuations. Metabolite concentrations of APrcEO's also varied seasonally, and were higher in the winter due to lower water temperature. Nonylphenol had less season variability than other metabolites of APrcEO's. Sediments were investigated and nonylphenol was the predominant nonylphenolic compound with concentrations of 364 to 5,100 times that found in the river water. Treatment conditions within the treatment plants along the Glatt River system were studied and the abundance of particular metabolites of APrcEO's were dependent on the treatment conditions (Ahel et al. 1994a; Ahel et al. 2000). Another study by Ahel et al. (1996) demonstrated that nonylphenol can be reduced in ground water probably by biological processes provided that the ground water temperature does not become too cold for biological degradation. It has been demonstrated (Ahel et al. 1994c) that nonylphenol can be degraded by photochemical processes in 10 to 15 hrs (half-life) in bright summer sun when nonylphenol is near the water surface. Heinis et al. (1999) studied the distribution and persistence of nonylphenol in temperate climate zone natural pond systems. They reported that nonylphenol partitioned to the pond enclosure wall ------- I material, macrophytes, and sediments within two days. After 440 days, the primary sink for nonylphenol was the sediment. Dissipation time from the sediment for 50 and 95 percent were estimated at 66 and 401 days, respectively. Measurable concentrations of nonylphenol can persist for many years in sediments. Hale et al. (2000) measured nonylphenol concentrations in sediments below wastewater outfalls and found one site that had a sediment concentration of 54,400 ,ug/kg more than twenty years after the treatment plant ceased operation. Bennett and Metcalfe (1998; 2000) found that nonylphenol was widely distributed in the lower Great Lakes sediments and reached 37,000 Aig/kg in sediments near sewage treatment plants. It appears that degradation of nonylphenol in sea water may be slower than in fresh water. This was observed in both water and sediments. Ekelund et al. (1993) found that initial nonylphenol degradation was slow in sea water, but after microorganism adaptation occurred, the degradation rate increased. Approximately 50 percent of the nonylphenol was degraded after 58 days. In marine sediments, the rate of degradation was initially faster than hi water, but about the same percentage was degraded in 58 days as in sea water. Ethoxylated nonylphenol, in marine sediments, has a half-life of 60 days similar to nonylphenol (Shang et al. 1999). Nonylphenol is metabolized by hepatic cytochrome P450 enzymes in the rainbow trout (Oncorhynchus mykiss), and bile from the fish contained the glucuronic acid conjugates of nonylphenol (Meldahl et al. 1996; Thibaut et al. 1999). Arukwe et al. (2000) found that bile was the major route of nonylphenol excretion with a half-life of 24 to 48 hrs in both waterborne and dietary exposures. The Log P of nonylphenol ranges from 3.80 to 4.77, indicating the possibility of bioaccumulation in aquatic organisms. Bioconcentration was measured in two saltwater organisms, blue mussel (Mytilus edulis) and Atlantic salmon (Salmo solar). The estimated bioconcentration factor (BCF) for the blue mussel ranged from 1.4 to 7.9 (McLeese et al. 1980a), and the Atlantic salmon estimated BCF was 75 (McLeese et al. 1981). Ahel et al. (1993) measured the bioconcentration of nonylphenol in rivers hi Switzerland. They found that nonylphenol was bioconcentrated approximately 10,000 times in algae, but this concentration was not further concentrated up the food chain. Instead, they measured lower bioconcentration factors in fish and ducks than in plants. Nonylphenol has been tested for its ability to bind to estrogen receptors. There are several review articles that describe disruption of endocrine function by nonylphenol (Servos 1999; Sonnenschein and Soto 1998; Sumpter 1998). It has been found to bind to estrogen receptors in cell cultures (Flouriot et al. 1995; Hewitt et al. 1998; Jobling and Sumpter 1993; Lutz and Kloas 1999; ------- Routledge and Sumpter 1996; Soto et al. 1991, 1992; White et al. 1994) and whole animals (Jobling et al. 1996). Optimal estrogenic activity requires a single tertiary branched alkyl group composed of six to eight carbons located at the para position on an otherwise unsubstituted phenol ring (Routledge and Sumpter 1997). Tabira et al. (1999) found that when using human estrogen receptors, the receptor binding of alkylphenols was maximized when the number of alkyl carbons was nine as it is with nonylphenol. Nonylphenol is able to stimulate the liver of male and immature female fish to produce the egg-yolk precursor protein vitellogenin, which is normally found in high concentrations only in mature female fish. Islinger et al. (1999) estimated the estrogenic potential of nonylphenol to stimulate vitellogenin production in male rainbow trout at 2,000 to 3,000 times less potent than 17 p-estradiol. It is also able to cause changes in the spermatogenesis cycle of male fish. Ren et al. (1996a) demonstrated significant increases in the estrogenic effects in rainbow trout exposed to nonylphenol at 100 Mg/L for 72 hr using vitellogenin production as a biomarker. In another study, Ren et al. (1996b) demonstrated that nonylphenol could stimulate the production of vitellogenin mRNA in four hr at a concentration as low as 10 p-g/L. Nonylphenol at concentrations of 50 and 100 /^g/L caused 50 and 86 percent, respectively, of the male Japanese medaka (Oryzias latipes) fish to develop an intersex condition (both testicular and ovarian tissues in the gonad) with a three month exposure (Gray and Metcalfe 1997). The sex ratio shifted in favor of females at the highest treatment. Purdom et al. (1994) found that rainbow trout held in cages in the outfalls of sewage treatment plants had increased vitellogenin concentrations in the blood. They suggested that the two most likely estrogenic substances present in the effluents were ethynylestradiol and nonylphenol. Several studies (Allen et al. 1999, Harries et al. 1997, Lye et al. 1999, Tanghe et al. 1999) conducted in Europe have attempted to demonstrate that waters in various rivers and estuaries below sewage treatment plants have the ability to induce estrogenic effects in a yeast assay and in fish. Effects were seen in most areas sampled and the possibility of mixture effects with nonylphenol, other xenoestrogens, and human estrogens exists. A comprehension of the "Guidelines" for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" (Stephan et al. 1985), hereinafter referred to as the "Guidelines," and the response to public comments concerning that document (U.S. EPA 1985) is necessary to understand the following text, tables, and calculations. Results of such intermediate calculations as recalculated LC50s and Species Mean Acute Values are given to four significant figures to prevent roundoff error in subsequent calculations, not to reflect the precision of the value. The U.S. Environmental Protection Agency has modified its original intention of requiring testing for ------- nonylphenol-mixed isomers (CAS No. 25154-52-3) and now recommends testing to be conducted with the chemical substance comprised of mostly para-branched C9-alkylphenols with CAS No- 84852-15-3 (Federal Register 1990). The criteria presented herein are the agency's best estimate of maximum concentrations of the chemical of concern to protect most aquatic organisms, or their uses, from any unacceptable short- or long-term effects. Freshwater criteria were derived using nonylphenol of CAS numbers 25154-52-3 and 84852-15-3; saltwater criteria were derived using only nonlyphenol of CAS number 84852-15-3. The latest comprehensive literature search for fresh- and saltwater information for this document was conducted in November, 1999. Some newer information has been included. Acute Toxicitv To Aquatic Animals Data that are suitable, according to the "Guidelines," for the derivation of a freshwater Final Acute Value (FAV) are included hi Table 1. Eighteen species and two subspecies representing fifteen genera were tested with nonylphenol to determine its acute toxicity to these species. Acute toxicity test results ranged from 55.72 /zg/L for an amphipod (Hyalella aztecd) to 774 ,ug/L for a snail (Physella virgata). The most sensitive freshwater species tested was an amphipod, Hyalella azteca (Tables 1 and 3). Brooke (1993a) and England and Bussard (1995) tested this species under similar conditions, except for water hardness levels which were 51.5 and 148-154 mg/L as CaCO3, respectively. An LC50 of 20.7 //g/L.was calculated in the lower hardness water and 150 /ug/L in the higher hardness water. However, insufficient data exist to demonstrate an effect of water hardness on the toxicity of nonylphenol. Tadpoles of the boreal toad, Bufo boreas, were ranked second in sensitivity to nonylphenol (Dwyer et al. 1999a) and had a 96-hr LC50 of 120 Mg/L. Data for one cladoceran species (Daphnia magna) are available. Brooke (1993a) reported an EC50 of 84.8 /zg/L from a test that had the solutions renewed daily and Comber et al. (1993) reported an EC50 of 190 /ug/L in a static test. The Daphnia magna Species Mean Acute Value is 126.9 /^g/L. Freshwater fish species were in the mid-range of toxicity to nonylphenol. Toxicity test results are available for eleven species representing eight genera. Their sensitivity to nonylphenol ranged from 133.9 ^g/L for the fathead minnow (Pimephalespromelas) to 289.3 //g/L for the bonytail chub (Gila elegans}. Three trout species of the genus Oncorhynchus and two subspecies were tested and had similar LC50s ranging from 140 to 270 /^g/L. Dwyer et al. (1995, 1999a) exposed nine species offish that were surrogates of threatened or endangered fish species or were threatened and endangered. ------- Acute toxicity test results were based upon static tests with unmeasured nonylphenol concentrations and the LC50s ranged from 110 ^g/L for the fountain darter, Etheostoma rubrum, to a geometric mean of 289.3 /zg/L for the bony tail chub. The least sensitive freshwater species to nonylphenol toxicity were invertebrates. The annelid worm (Lumbriculus variegatus) had an LC50 of 342 //g/L, nymphs of the dragonfly Ophiogomphus sp. had an LC50 of 596 //g/L and the least sensitive species tested was a snail, Physella virgata, which had an LC50 of 774 ,ug/L. The lower sensitivity to nonyphenol occurs even though this species of snail does not have an operculum and would not be able to completely enclose its body and thus protect itself against nonylphenol exposure. Freshwater Species Mean Acute Values (SMAV) and Genus Mean Acute Values (GMAV) were derived from available acute values (Tables 1 and 3). GMAVs were available for 15 genera; the most sensitive was the amphipod, H. azteca, which was 13.9 times more sensitive than the least sensitive species,, a snail P. virgata (Figure 1). The four most sensitive species were within a factor of 2.4 of one another. The freshwater Final Acute Value (FAV) for nonylphenol is 55.71 //g/L and was calculated using the procedure described in the "Guidelines" and the GMAVs in Table 3. The FAV is equal to the lowest freshwater SMAV of 55.72 //g/L for the amphipod H. azteca. The acute toxicity of nonylphenol to saltwater animals has been tested with seven invertebrate and three fish species (Table 1). The range of SMAVs extends from 17 ,ug/L for the winter flounder, Pleuronectes americanus, -to 209.8 /^g/L for the sheepshead minnow, Cyprinodon variegatus (Lussier et al. 2000; Ward and Boeri 1990b), a difference of 12.3 times. Fish (winter flounder), bivalves (coot clam, Mulinia lateralis} and crustaceans (the mysid, Americamysis bahia) were all among the most sensitive species. Data for nine of the twelve saltwater test values reported in Table 1 were from a single multi- species test (Lussier et al. 2000). Nonylphenol concentrations were measured in seven of the nine tests (Table 1), with measurements made at test initiation and at the end of the test (48 or 96 hr). Test organisms were fed brine shrimp, Anemia sp., during test chemical exposure. Normally this is not acceptable for data used to derive Final Acute Values. However, the tests reported by Lussier et al. (2000) were designed to extend beyond the usual 48 or 96-hr acute test interval to 168 hr. The extended exposure time required feeding to ensure survival of animals not affected by nonylphenol. The brine shrimp fed during the tests were "reference grade" and not likely to change the exposure to nonylphenol. Two animal species were tested in two laboratories allowing comparison of results from ------- IslMIFT a study with food added and another without food. In the case of the mysid, 96-hr LC50s were estimated at 43 and 60.6 //g/L for the non-fed and fed studies, respectively. The sheepshead minnow had 96-hr LC50s of 310 and 142 /^g/L for the respective non-fed and fed studies. Because feeding during the tests did not consistently raise or lower the LC50 estimates, feeding is assumed not to have altered the results in these tests. Therefore, the data from the Lussier et al. (2000) tests were acceptable for deriving a saltwater Final Acute Value. GMAVs for the four most sensitive saltwater species differ by a factor of only 3.5 (Table 3 and Figure 2). Using the method of calculation specified in the "Guidelines," the saltwater FAV is 13.35 /ug/L. The FAV is lower than the lowest SMAV of 17 //g/L for the winter flounder. Chronic Toxicity To Aquatic Animals The available data that are usable according to the "Guidelines" concerning the chronic toxicity of nonylphenol are presented in Table 2. England (1995) exposed neonates of a cladoceran, Ceriodaphnia dubia, to nonylphenol for seven days in a renewal test. The results showed a significant reproductive impairment at 202 /j-g/L, but not at 88.7 //g/L, and survival was reduced at 377 //g/L, but not at 202 ^g/L. Based upon reproductive impairment, the Chronic Value for C. dubia was 133.9 //g/L. At the end of 48 hr in the same test, effects were observed and an EC50 of 69 /ug/L was calculated. However, the animals had received food and according to the "Guidelines," acute tests with this species must not receive food during an acute toxicity test if the test is to be valid and used to compute an Acute-Chronic Ratio (ACR). Fliedner (1993) exposed 4 to 24 hr-old Daphnia magna neonates to nonylphenol for 22 days in a 20°C life-cycle test. Test solutions were renewed three times each week during which a 52.2 to 65.5 percent decrease in nonylphenol concentration was measured. Mean measured nonylphenol test concentrations were: 0, 0, 1.55, 1.34, 3.45, 10.70, and 47.81 Aig/L. No effects were observed during the study on the mortality, the number of offspring per female, or the mean day of the first brood. A significant effect was measured for the total number of young per concentration on day nine of the study. Consequently, the No Observed Effect Concentration (NOEC) was 10.7 //g/L and the Lowest Observed Effect Concentration (LOEC) was 47.8 /j.g/L with a chronic value (geometric mean of the NOEC and LOEC) of 22.62 ^g/L. An acute test was not conducted to calculate an ACR. Brooke (1993a) also reported a chronic exposure for the cladoceran Daphnia magna, but for 21-days. Test solutions were renewed three times per week and concentrations of nonylphenol ------- I declined an average of 57.4 + 5.8 percent between solution renewals. The author concluded that D. magna were significantly impaired in growth and reproduction at 215 y^g/L, but not at 116 ^g/L. Survival was reduced to 60 percent at 215 /ug/L; however, this survival rate was not a significant reduction from the control survival rate because only 80 percent survived in the control group. The Chronic Value estimated from the geometric mean of the lower (116 //g/L) and upper (215 //g/L) chronic limits based upon reproductive impairment was 157.9 /^g/L. Division of the chronic value for this test (157.9 /ug/L) into the 48-hr EC50 from a companion test (84.8 //g/L) resulted in an ACR of 0.5370. The calculated ratio of 0.5370 was changed to 2.000 as suggested in the "Guidelines" because acclimation to nonylphenol probably occurred during the chronic test. A third D. magna life-cycle 21-day exposure to nonylphenol was conducted by Comber et al. (1993). They found no significant effects in survival, reproduction or growth at concentrations <24 //g/L. Reproduction was significantly reduced at concentrations >39 /ug/L when the number of live young produced was compared to control reproduction. Growth was reduced at concentrations >71 //g/L and survival of adults was reduced at concentrations >130 yug/L. Based upon reduced reproduction at 39 //g/L but not at 24 //g/L, the Chronic Value was 30.59 yug/L. Division of the Chronic Value (30.59 /ug/L) for this test into (he 48-hr EC50 of 190 //g/L from a companion study resulted in an ACR of 6.211. Because two ACRs were available for D. magna, the geometric mean of the two values was used as the species-mean ACR. The species-mean ACR for D. magna is 3.524. The midge, Chironomus teutons, was exposed to five concentrations of nonylphenol and a control from < 24-hr old larva through emergence (53 days) as adults (Kahl et al. 1997). Nominal exposure concentrations ranged from 12.5 to 200 //g/L, but mean measured concentrations were lower. Neither growth or reproductive (sex ratio, emergence pattern, and egg production and viability) measurements were negatively affected at any of the exposure concentrations. There was a significant effect upon survival of larvae during the first 20 days of exposure, but none after 20 days. The LOEC was 91 //g/L, based upon survival at 20 days, and the NOEC was 42 //g/L. The Chronic Value is 61.82 //g/L. An acute exposure was not conducted; therefore, an ACR can not be calculated for this species. A 91-day early life-stage test was conducted with embryos and fry of the rainbow trout, Oncorhynchus mykiss (Brooke 1993a). Five nonylphenol exposure concentrations were tested and they ranged from 6.0 to 114 //g/L in the flow-through test. Time to hatch and percent survival at hatch ------- were not affected by the nonylphenol concentrations; however, nearly all of the larvae were abnormal at the two highest exposure concentrations (>53.0 //g/L). At the end of the test, survival was significantly reduced at concentrations >23.1 /^g/L but not at 10.3 Mg/L. Growth (both weight and length) was a more sensitive chronic endpoint than survival. At the end of the test, the fish were significantly shorter (14 percent) and weighed less (30 percent, dry weight) at concentrations >10.3 ^g/L than the controls, but not at 6.0 //g/L. Based upon growth, the Chronic Value for rainbow trout was 7.861 /^g/L. A companion acute test was available for this species. Division of the Chronic Value (7.861 ^g/L) into the Acute Value (221 //g/L) yielded an ACR of 28.11 for rainbow trout. An early-life-stage toxicity test was conducted with nonylphenol and the fathead minnow, Pimephales promelas (Ward and Boeri 1991c). Embryos and larvae were exposed for a total of 33 days to five concentrations of nonylphenol that ranged from 2.8 to 23 //g/L. Embryos in the control and those in the three lowest nonylphenol exposure concentrations (2.8, 4.5, and 7.4 /^g/L) began to hatch on the third day of exposure, while the two higher concentrations (14 and 23 //g/L) began hatching on the fourth day. Growth (length or weight) was not significantly different from the control organisms at an}' of the treatment exposures. Survival of the fish at the end of the test was significantly reduced at nonylphenol concentrations > 14 //g/L. Fish survival averaged 56.7 percent at the 23 /ig/L exposure, 66.7 percent at the 14 /^g/L exposure, and 76.7 percent at the 7.4 /^g/L exposure, only concentrations <7.4 fig/L did not differ from the control that averaged 86.7 percent survival. Based upon survival, the LOEC for the fathead minnow was 14 //g/L and the NOEC was 7.4 ^g/L. The Chronic Value was 10.18 /^g/L (Table 2). No companion acute toxicity test was conducted with the fathead minnow with which an ACR can be calculated. The chronic toxicity of nonylphenol to saltwater animals was determined in a 28-day life-cycle test with mysids, Americamysis bahia (Ward and Boeri 1991b). There was no effect on survival or reproduction at 6.7 //g/L, but there was a 18 percent reduction in survival and a 53 percent reduction in reproduction at 9.1 fj-g/L. Effects on survival at the highest concentration tested (21 /^g/L) were observed before the end of the third week of the test. Test organisms of each sex were measured separately for length and weight. The data show no obvious difference between the length of male and female mysids for all of the concentrations tested. The growth analysis was based on combined length data for both sexes. Growth (length) was the most sensitive endpoint for mysids. There was a 7 percent, but statistically significant, reduction in the length of mysids exposed to 6.7 //g/L of nonylphenol relative to control mysids. There was not a significant difference in growth for mysids 10 ------- exposed to 3.9 /zg/L nonylphenol when compared to control animals (Table 2). The Chronic Value, based on growth, for mysids was the geometric mean of the lower (3.9 /ug/L) and the upper (6.7 //g/L) Chronic Values and was 5.112 ^g/L. The ACR of 8.412 was calculated using the acute value of 43 Mg/L from a companion study and dividing by the Chronic Value of 5.112 ^g/L. Three valid ACRs are available for nonylphenol using the third and eighth (Table 3) most sensitive tested species of freshwater animals and the third most sensitive saltwater animal. Two ACRs were available for the cladoceranDaphnia magna, which differed by a factor of approximately 3.1 times. The geometric mean of these two values is 3.524. The cladoceran, Ceriodaphnia dubia, had an ACR ratio of 0.515 when using the tests of England (1995). However, this ratio was derived using the results of the companion acute test during which the organisms were fed. According to the "Guidelines," acute tests with this species must be done without food present in the test solutions. Therefore, the C. dubia ACR was not used. The three valid ACRs (3.524, 8.412 and 28.11) differed by a maximum of 7.98 times (Table 3). The largest ACR was for a fish (rainbow trout) that represented the eighth most sensitive genera of the fifteen tested from fresh water. The geometric mean of the three valid ACRs was 9.410, which is the Final Acute-Chronic Ratio (FACR). Toxicity To Aquatic Plants Only a single species of freshwater plant has been tested that meets the requirements for inclusion in Table 4 according to the "Guidelines." Ward and BoerL(1990a) exposed green algae (Selenastrum capricomutum) to nonylphenol for four days. They calculated an EC50 of 410 ^g/L based upon cell counts. At the end of the toxicity test, algae from the highest exposure concentration (720 //g/L) were transferred to fresh media solution. During the next seven days, cell counts increased exponentially indicating that nonylphenol treatment at this concentration for four days did not have a persistent algistatic effect. Acceptable data on the toxicity of nonylphenol to saltwater plants were available for one species of marine algae (Table 4). The EC50 value for vegetative growth of the planktonic diatom, Skeletonema costatum, was 27 ^g/L (Ward and Boeri 1990d). Although this value was lower than nearly all of the acute values for animals, it is for vegetative growth, which can recover rapidly. Skeletonema transferred from the highest nominal concentration of nonylphenol with survivors (120 ^g/L) into control medium grew to a 76-fold increase in cells/mL within 48 hr (Ward and Boeri 1990d). 11 ------- Based on the vegetative growth test using the saltwater planktonic diatom, Skeletonema costatum, the Final Plant Value for nonylphenol is 27 /ig/L. This plant species is more sensitive to nonylphenol than any tested species of freshwater animal and more sensitive than all but one tested saltwater animal species. Bioaccumulation Three studies were conducted to measure the bioconcentration of nonylphenol in freshwater animals that, according to the "Guidelines," meet the requirements for inclusion in this section of the document (Table 5). Ward and Boeri (1991a) measured the whole body burden in juvenile fathead minnows, with bioconcentration determined at two exposure concentrations (4.9 and 22.7 //g/L) after 27 days of exposure. The bioconcentration factors were not lip id normalized and were similar at 271 and 344 times for the respective lower and higher exposure concentrations. Brooke (1993b) exposed juvenile fathead minnow (Pimephales promelas) and juvenile bluegill (Lepomis macrochirus) to nonylphenol each at five concentrations for four and twenty-eight days. Lipid concentrations were measured (Brooke 1994) for the test fish and the bioconcentration results were lipid normalized which reduced the bioconcentration factors from 4.7 to 4.9 times. Nonylphenol concentrations that proved lethal to the organisms were not used to compute bioconcentration factors. The short-term (4 day) tests showed that plateau tissue concentrations were reached within two days in both the fathead minnow and the bluegill. Therefore, there was generally good agreement between the 4- and 28-day tests. Normalized bioconcentration factors for the fathead minnow ranged from 128.3 to 209.4 (Table 5). Normalized bioconcentration factors for the bluegill ranged from 38.98 to 56.94. Giesy et al. (2000) measured me concentration of nonylphenol in the whole bodies of the fathead minnow following a 42-day exposure. Three sublethal concentrations allowed nonylphenol to bioaccumulate 203 to 268 times in exposure concentrations ranging from 0.4 to 3.4 ^g/L. _ Bioconcentration factors are available (Ekelund et al. 1990) for three species of saltwater animals, Mytilus edulis, Crangon crangon and Gasterosteus aculeatus (Table 5). Dosing was with 14C- labeled nonylphenol, but the CAS number was not listed. (Crangon crangon is a non-resident species, but the data are included since very little bioaccumulation data are available.) Exposures lasted 16 days followed by an elimination period of 32 days. Lipid normalized bioconcentration factors based on wet weight ranged from 78.75 for C. crangon to 2,168 for M. edulis. The steady state tissue concentration for M. edulis was estimated since it did not reach steady state after only 16 days of 12 ------- MT exposure. No U.S. FDA action level or other maximum acceptable concentration in tissue, as defined in the "Guidelines," is available for nonylphenol. Therefore, a Final Residue Value cannot be calculated. Other Data Additional data on the lethal and sublethal effects of nonylphenol on freshwater species that do not comply with data requirements described in the "Guidelines" for inclusion in other tables are presented in Table 6. Three plant species (Chlamydomonas reinhardni, Salvinia molesta, Lemna minor) were exposed in studies using media solutions that were not described. The results generally showed the plant species to be less sensitive to nonylphenol than animals. One test with the duckweed, Lemna minor, was an exception and showed a four-day reduction in vegetative growth at 125 ^g/L (Prasad 1986). McLeese et al. (1980b) reported LCSOs of 5,000 Aig/L for a clam, Anodonta cataractae, in a 144-hr exposure and 900 //g/L for the Atlantic salmon, Salmo solar, in a 96-hr exposure. The values were higher than those reported in Table 1 for similar species. The test organisms were fed in both tests. Three long-term (21 day) tests with Daphnia magna (Baer and Owens 1999, Baldwin et al. 1997, LeBlanc et al. 2000) and a single long-term (30 day) test with D. galeata mendotae (Shurin and Dodson 1997) are included in this section because the tests were conducted without measurement of nonylphenol concentrations in the test water. The results in the unmeasured tests agree reasonably well with those measured and reported in Table 2 for D. magna. Negative effects on survival or reproduction were observed in all three tests between 25 and 200 //g/L. The cladoceran, Daphnia pulex, was exposed for 48 hr in tests in which nonylphenol concentrations decreased more than 50 percent during the exposures (Ernst et al. 1980), but resulting LC50s ranged from 140 to 190 //g/L, which agreed with LC50s for other cladoceran species. The cladoceran, Ceriodaphnia dubia, gave similar LC50 results of 276 and 225 ^g/L for the respective exposure durations of 48 hr and 7 days (England 1995). The LC50 values reported in this table for the species are slightly higher than the Chronic Value for the species of 134 ptg/L (Table 2). England and Bussard (1993) reported an EC50 and an LC50 for larva of the midge, Chironomus tentans, of 95 and 119 Aig/L, respectively. These values were slightly more sensitive than values reported in a similar study in which food was not available (Table 1). In a pair of tests in which the test organisms were fed, Brooke (1993b) measured a 96-hr LC50 for the fathead minnow, Pimephales promelas, of 138 /u.g/L and a 96-hr LC50 for the 13 ------- bluegill, Lepomis macrochirus, of 135 /^g/L. The LC50 values for these species from tests in which the fish were fed, agree well with data from tests in which the fish were not fed (Table 1). Five fish species (rainbow trout, lahontan cutthroat trout, apache trout, Colorado squawfish and fathead minnow) were exposed to nonylphenol for 96 hr to determine if nonylphenol inhibited brain acetylcholoinesterase enzymes. Response to AchE inhibition was measured by a decrease in the number of muscarinic cholinergic receptors which is a compensatory response to an acetycholine buildup (Jones et al. 1998). Responses at exposure concentrations <220 //g/L were observed in the rainbow trout, lahontan cutthroat trout, and apache trout. Brooke (1993b) measured the bioconcentration of nonylphenol in the fathead minnow and bluegill at concentrations near lethality. The fathead minnow BCF was 100.4 and the bluegill BCF was 35.31. The values were slightly less than the BCFs measured in the fish from lower exposure concentrations (Table 5). Lewis and Lech (1996) found that bioconcentration of nonylphenol was highest (BCF=98.2) in the viscera of rainbow trout and 24.21 in the remainder of the carcass. They also measured the half-life of nonylphenol in various tissues and found that fat and muscle similarly depurated nonylphenol to half concentrations in about 19 hr. The liver depurated to half concentrations in about 6 hr. Mesocosm studies were conducted with nonylphenol in which zooplankton, benthic macroinvertebrates, and fish were observed for effects. The exposure was for 20 days with four nonylphenol concentrations. Zooplankt; n populations (O'Halloran et al. 1999) and benthic macroinvertebrate populations (Schmude et al. 1999) showed no negative effects at the 23 /Lig/L nonylphenol exposure concentration, and were negatively affected at 76 //g/L. Various species of zooplankton and macroinvertebrates exhibited differences in sensitivity to nonylphenol. The authors of the zooplankton study stated that a MATC for the protection of all zooplankton taxa is ~ 10 //g/L. The fish (bluegill) in the mesocosms (Liber et al. 1999) were unaffected at nonylphenol exposures <76 ^g/L, but survival was reduced at 243 /ug/L. In one exposure replicate with a mean nonlyphenol concentration of 93 ^g/L, survival of the fish was reduced after 20 days of exposure indicating that concentrations near 100 /ug/L may be maximal for this species. The mesocosm studies demonstrated that the freshwater Final Chronic Value of 5.920 //g/L should be protective of aquatic life. Nonylphenol does have estrogen-like qualities. Vitellogenin is a protein produced in the liver of female oviparous vertebrate species and deposited in the ovaries as the primary material for yolk in the ova. Male fish normally produce very little vitellogenin. Jobling et al. (1996) demonstrated 14 ------- significant increases in vitellogenin in male rainbow trout, Oncorhynchus my kiss, at three weeks of exposure to 20.3 and 54.3 /j.g/L of nonylphenol. Lech et al. (1996) observed a significant increase in mRNA for the vitellogenin gene in rainbow trout at 14.14 //g/L. A long-term study was conducted with rainbow trout, Onchorynchus mykiss, exposing female fish immediately after hatch to 1, 10, and 30 or 50 jug/L of nonylphenol (Ashfield et al. 1998). They found reduced growth in fish exposed to 1 Mg/L for 22 days and grown for 86 days beyond treatment. Growth was not reduced in the 10 //g/L treatment but was in the 50 ^g/L treatment. A second study was conducted and exposure was for 35 days and grow-out was for 431 days beyond the last treatment day. On day 55 of the study, reduced growth was observed at the 10 and 30 ,ug/L treatments, but not at the 1 ^g/L. At day 466, the fish exposed to 10 /^g/L recovered the growth reductions seen earlier and only the 30 ^g/L exposed fish showed reduced (-25 percent) growth. The ovosomatic index (increase in ovary size relative to the control fish ovaries) increased in the fish exposed to 30 //g/L at day 466. The authors speculated that the growth reduction may have been caused by the use of energy for precocious sexual development. A non-resident fish species, Japanese medaka (Oryzias latipes}, was exposed to nonylphenol for 28 days following hatching (Nimrod and Benson 1998). The survivors were monitored for the following 55 days. At the highest exposure concentration of 1.93 f^-g/L, survival, growth, egg production, egg viability, and gonadosomatic index (GSI) were not altered. In another study with the same species of fish, development of testis-ova, an intersex condition, occurred after a three month exposure to 50 ^g/L of nonylphenol (Gray and Metcalf 1997). An increase in the number of Sertoli cells may have occurred in the male fathead minnow exposed to nonylphenol at 1.6 /J.g/L for 42 days (Miles -Richardson et al. 1999). The evidence was not complete, but indicated the possibility of increased phagocytic action and Sertoli cell tissue in testes. The condition may negatively affect sperm production or survival. In a companion study with the fathead minnow, Giesy et al. (2000) found that nonylphenol exposures of >0.4 //g/L depressed fecundity, concentrations of <3.4 //g/L did not change vitellogenin concentrations in the blood of males, and raised the 17 p-estradiol liters in the blood of male and female fish at concentrations >0.05 /ug/L. The characteristic of nonylphenol to induce estrogenic effects has seldom been reported at concentrations below the freshwater Final Chronic Value of 5.920 f^g/L. More studies are needed to achieve a better understanding of the role of nonylphenol in estrogen mimicry. Additional data on the lethal and sublethal effects of nonylphenol on saltwater species that do not comply with data requirements described in the "Guidelines" for inclusion in other tables are 15 ------- presented in Table 6. Results from a sexual reproduction test with red alga species, Champia parvula, indicated that reproduction was not inhibited at the highest measured concentration tested, 167 ^g/L (Tagliabue 1993). Cypris larva of the barnacle, Balanus amphitrite, were exposed to nonylphenol for 48 hi and the settlement of the larva was reduced at 1.0 /zg/L (Billinghurst et al. 1998). The soft-shell clam, My a arenaria, showed no adverse effects on survival from a 360-hr exposure at 700 /^g/L (McLeese et al. 1980b). Nonylphenol reduced byssus thread strength in the blue mussel Mytilus edulis (Granmo et al. 1989) at concentrations >56 //g/L. Nonylphenols also show promise as antifouling agents when compared with other alkyIphenols, copper, and tributyl tin (Takasawa et al. 1990). The antifouling test results, however, are qualitative. Nonylphenol concentrations extracted from sediments in the Venice, Italy lagoon were higher in areas with large masses of decomposing macroalgae (primarily Ulva rigida) than in areas not associated with the decomposition (Marcomini et al. 1990). This suggests that nonylphenol bioaccumulated by the macroalgae was transferred to trie sediment as the algae died and decomposed. McLeese et al. (1980b) reported 96-hr test results for the Atlantic salmon, Salmo solar, that were in general agreement with freshwater trout test results. In four tests, LC50 values ranged from 130 to 900 jUg/L. Ward and Boeri (1990c) found similar toxicity results for sheepshead minnow, Cyprinodon variegatus, exposed in brackish water as those reported for salt water (Table 1). In brackish water, LC50's ranged from >420 ^g/L for a 24-hr exposure to 320 //g/L for a 72-hr exposure. KUlifish (Kelly -and Di Giulio 2000) were exposed as embryos and larva to nonylphenol for 96 hrs. Even though the solvent concentration used in the exposures exceeded the 0.5 mL/L recommended limit, the data are included in Table 6 because the results reported for the solvent controls do not show decreased hatching success or increased abnormalities at 10 days post-hatch. Embryos exposed to 2,204 /^g/L for 96 hr were all abnormally developed at 10 days post-fertilization. The LC50 for the same exposure period was 5,444 ^g/L. Killifish larva were similar in sensitivity to nonylphenol exposures at post hatch ages of 1, 14, and 28 days with LCSO's of 214, 209, and 260, respectively. Additional data on the effect of nonylphenol on saltwater species do not indicate greater sensitivities than indicated previously. Some of the data presented in Table 6 were from the same acute tests listed in Table 1 (Lussier et al. 2000; Ward and Boeri 1990a,b), but for exposure durations other than 96 hr. 16 ------- Unused Data Some data concerning the effects of nonylphenol on aquatic organisms and their uses were not used because the tests were conducted in mixtures of chemicals (i.e., Ahel et al. 1993; Amato and Wayment 1998; Dwyer et al. 1999a; Escher et al. 1999; Larsson et al. 1999; Moore et al. 1987; Purdom et al. 1994; Sundaram et al. 1980; Turner et al. 1985) or in sediments (i.e., Fay et al. 2000; Hansen et al. 1999; Ward and Boeri 1992). Andersen et al. (1999); Celius et al. (1999); Jobling and Sumpter (1993); Knudsen and Pottinger (1999); Lamche and Burkhardt-Holm (2000); Levine and Cheney (2000); Loomis and Thomas (1999); Milligan et al. (1998); Petit et al. (1997, 1999) exposed excised cells in tissue cultures. Data were not used when organisms were dosed by injection (i.e., Arukwe et al. 1997a,b, 1998; Christiansen et al. 1998a,b,c; Coldham et al. 1997, 1998; Haya et al. 1997; Madsen et al. 1997; Nirnrod and Benson 1996, 1997; Spieser et al. 1998; Yadetie et al. 1999) or gavage (i.e., Rice et al. 1998; Thibaut et al. 1998). Data were not used when generated in an artificial medium (i.e., Weinberger et al. 1987). Tsuda et al. (2000) measured tissue concentrations from feral fish, but water concentrations greatly varied. Some studies were conducted with only the ethoxylated nonylphenols (i.e., Baldwin et al. 1998; Braaten et al. 1972; Dorn et al. 1993; Maki et al. 1998; Manzano et al. 1998, 1999; Patoczka and Pulliam 1990). Bearden and Schultz (1997, 1998); Lewis (1991); Liber et al. (1999); Varma and Patel (1988) and Veith and Mekenyan (1993) compiled data from other sources. Results were not used when the test organism or the test material were not adequately described (e.g., Folmar et al. 1998; Hansen et al. 1998; Kopf 1997; Magliulo et al. 1998; Midler 1980; Palmer et al. 1998; Weinberger and Rea 1981). Summary Acute toxicity of nonylphenol was tested in eighteen species and two subspecies representing fifteen genera of freshwater organisms. Toxicity values ranged from 55.72 //g/L for the amphipod Hyalella azteca to 774 ^g/L for the snail Physella virgata. For the four most sensitive tested freshwater species, two were invertebrates and two were vertebrate species (Figure 1). No relationships have been demonstrated between water quality characteristics (such as hardness and pH) and toxicity. Eleven species of fish were tested and were in the mid-range of sensitivity (133.9 to 289.3 ,ug/L) of tested species. The freshwater Final Acute Value (FAV) is 55.71 //g/L which is equal to the LC50 for the most sensitive tested species, Hyalella azteca. Acute toxicity has been tested with ten species of saltwater organisms (Figure 2). Species Mean Acute Values ranged from 17 //g/L for 17 ------- the winter flounder, Pleuronectes americanus, to 209.8 //g/L for the sheepshead minnow, Cyprinodon variegatus. The saltwater FAV is 13.35 //g/L. Chronic toxicity of nonylphenol was tested in five freshwater species and one saltwater species (Figure 3). The most sensitive species tested was the mysid Americamysis bahia and it had a Chronic Value (CV) of 5.112 /^g/L based on reduced growth. Two freshwater fish were tested; the rainbow trout, Oncorhynchus mykiss, had a CV of 7.861 ^g/L based on growth, and the fathead minnow, Pimephales promelas, had a CV of 10.18 //g/L based on survival. Two species of freshwater cladocerans were tested and CVs ranged from 22.62 to 157.9 /ug/L based on reproduction. One species of freshwater midge was tested and its CV was 61.82 ^g/L. Data were available to calculate a Final Acute-Chronic Ratio (FACR) for Daphnia magna, a freshwater cladoceran, saltwater mysid, Americamysis bdhia, and rainbow trout. The FACR for nonylphenol is 9.410. Two species of aquatic plants were exposed to nonylphenol. Plants were as sensitive as animals, showing effects that ranged from 27 to 410 /^g/L. Based on the vegetative growth test using the saltwater planktonic diatom Skeletonema costatum, the Final Plant Value for nonylphenol is 27 /xg/L. Nonylphenol bioaccumulates in aquatic organisms to low levels. In freshwater fish, lipid- normalized bioconcentration factors ranged from 39 to 209 times. Bioaccumulation was apparently greater in saltwater organisms where bioconcentration factors ranging from 78.75 to 2,168 were measured. Nonylphenol is considered an endocrine disrupter chemical and induces production of vitellogenin in male rainbow trout. This is a process normally occurring in female fish in response to estrogenic hormones during the reproductive cycle. It also induces precocious development of ovaries and an intersex condition in some fish species. National Criteria The procedures described in the "Guidelines" for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" indicate that, except possibly where a locally important species is very sensitive, freshwater organisms and their uses should not be affected unacceptably if the four-day average concentration of nonylphenol does not exceed 5.9 /zg/L more than once every three years on the average and if the one-hour average concentration does not exceed 27.9 fj-g/L more than once every three years on the average. Saltwater organisms and their uses should not 18 ------- be affected unacceptably if the four-day average concentration of nonylphenol does not exceed 1.4 //g/L more than once every three years on the average and if the one-hour average concentration does not exceed 6.7 //g/L more than once every three years on the average. Implementation As discussed in the Water Quality Standards Regulation (U.S. EPA 1983) and the Foreword to this document, a water quality criterion for aquatic life has regulatory impact only after it has been adopted in a State water quality standard. Such a standard specifies a criterion for a pollutant that is consistent with a particular designated use. With the concurrence of the U.S. EPA, States designate one or more uses for each body of water or segment thereof and adopt criteria that are consistent with the use(s) (U.S. EPA 1987, 1994). Water quality criteria adopted in State water quality standards could have the same numerical values as criteria developed under Section 304 of the Clean Water Act. However, in many situations States might want to adjust water quality criteria developed under Section 304 to reflect local environmental conditions and human exposure patterns. Alternatively, States may use different data and assumptions than EPA in deriving numeric criteria that are scientifically defensible and protective of designated uses. State water quality standards include both numeric and narrative criteria. A State may adopt a numeric criterion within its water quality standards and apply it either state-wide to all waters designated for the use the criterion is designed to protect or to a specific site. A State may use an indicator parameter or the national criterion, supplemented with other relevant information, to interpret its narrative criteria within its water quality standards when developing NPDES effluent limitations under 40 CFR 122.44(d)(l)(vi).2 Site-specific criteria may include not only site-specific criterion concentrations (U.S. EPA 1994), but also site-specific, and possibly pollutant-specific, durations of averaging periods and frequencies of allowed excursions (U.S. EPA 1991). The averaging periods of "one hour" and "four days" were selected by the U.S. EPA on the basis of data concerning how rapidly some aquatic species react to increases hi the concentrations of some pollutants, and "three years" is the Agency's best scientific judgment of the average amount of time aquatic ecosystems should be provided between excursions (Stephan et al. 1985; U.S. EPA 1991), However, various species and ecosystems react and recover at greatly differing rates. Therefore, if adequate justification is provided, site-specific and/or pollutant-specific concentrations, durations and frequencies may be higher or lower than those given in national water quality criteria for aquatic life. 19 ------- Use of criteria which have been adopted in State water quality standards for developing water quality-based permit limits and for designing waste treatment facilities requires selection of an appropriate wasteload allocation model. Although dynamic models are preferred for the application of these criteria (U.S. EPA 1991), limited data or other considerations might require the use of a steady-state model (U.S. EPA 1986). Guidance on mixing zones and the design of monitoring programs is available (U.S. EPA 1987, 1991). 20 ------- Figure 1. Ranked Summary of Nonylphenol GMAVs Freshwater. Ranked Summary of Nonylphenol GMAVs _J IUUU - *— " 0) c 0 *m lv 'c 0) o c o 0 100 : •4-1 O £ : LU "o c 0) ^ c o z 10 J Freshwater B • D D a D D D Q A ' Freshwater Rnal Acute Value = 55.7 uo/L Nonylphenol Criteria Maximum Concentration = 27.9 ug/L Nonylphenol I I I I I I I I I I 0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 • Invertebrates % Rank GMAVs DFisn A Amphibians 21 ------- Figure 2. Ranked Summary of Nonylphenol GMAVs - Saltwater. Ranked Summary of Nonylphenol GMAVs — IUUU q D) : w c o to Concent _i. § i i 1 1 1 1 1 1 Nonylphenol Effect -^ 0 O i . . , i , . , ,i Saltwater " D • Saltwater Final Acute Value = 13.4 ug/L Nonylphenol Criteria Maximum Concentration = 6.7 \ig/L Nonylphenoi I I I I I I I III 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 n/ i-» i ^-«> • •< < • Invertebrate % Rank GMAVs DRsh 22 ------- Figure 3. Chronic Toxicity of Nonylphenol to Aquatic Animals. Chronic Toxicity of Nonylphenol to Aquatic Animals IUUU - 5 0 : 3 "r5 'E o 10- O : - 1 - n D D Freshwater Final Chronic Value = 5.B ug/L Nonylphenol A Saltwater Final Chronic Value = 1.4 \ig/L Nonylphenol I I I I I I I I I I 0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 % Rank Genus Mean Chronic Value ° 'reshwater lnvertebrates I Freshwater Fish Saltwater Invertebrates 23 ------- Table 1. Acute Toxicity of Nonylphenol to Aquatic Animals Species Annelid (adult), Lumbriculus variegatus Snail (adult), Physella virgata Cladoceran (< 24-hr old), Daphnia magna Cladoceran (<24-hr old), Daphnia magna Midge (2nd instar), Chironomus teutons Dragonfly (nymph), Ophiogomphus sp. Amphipod, (juvenile, 2mm TL), Hyalella azteca Amphipod (juven., 2-3mm TL), Hyalella azteca Rainbow trout (0.67 ±0.35 g), Oncorhynchus mykiss Rainbow trout (1.25 +0.57 g), Oncorhynchus mykiss Rainbow trout (0.27 ±0.07 g), Oncorhynchus mykiss Rainbow trout (1.09 ±0.38g), Oncorhynchus mykiss Rainbow trout (0.48 ±0.08 g), Oncorhynchus mykiss Method" F,M F,M R,M S,M F,M F,M F,M F,M S,U S,U S,U s,u s,u LC50 or ECso11 Chemical pH (ng/L) FRESHWATER SPECIES >90% 6.75 342 >90% 7.89 774 >90% 7.87 84.8 91.8% 8.25 190 >95% 8.0-8.4 160 >90% 8.06 596 >90% 7.80 20.7 >95% 7.9-8.7 150 85% 7.8-7.9 190 85% 7.5-7.7 260 85% 7.9 140 85% 7.7-7.9 270 85% 7.5-7.9 160 Species Mean Acute Value (ng/L) Reference 342 Brooke 1993a 774 Brooke 1993a Brooke 1993a 126.9 Comber et al. 1993 160 England and Bussard 1995 596 Brooke 1993a Brooke 1993a 55.72 England and Bussard 1995 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 24 ------- Table I. Acute Toxicity of Nonylphenol to Aquatic Animals (continued) LL5 Species Rainbow trout (0.50 ±0.21 g), Oncorhynchus mykiss Rainbow trout (45 d), Oncorhynchus mykiss Apache trout (0.85 ±0.49 g), Oncorhynchus apache Apache trout (0.38 ±0.18 g), Oncorhynchus apache Greenback cutthroat trout (0.31 ±0.17g), Oncorhynchus clarki stomais Lahontan cutthroat trout (0.34 ±0.08 g), Oncorhynchus clarki henshawi Lahontan cutthroat trout (0.57 ±0.23 g), Oncorhynchus clarki henshawi Fathead minnow (0.32 ±0.16 g), Pimephales promelas Fathead minnow (0.56 ±0.19 g), Pimephales promelas Fathead minnow (0.45 ±0.35 g), Pimephales promelas Fathead minnow (0.40 +0.21 g), Pimephales promelas or Method" Chemical pJH (Mg/L) S,U 85% 6.5-7.9 180 F,M S,U S,U S,U S,U S,U S,U S,U S,U S,U >90% 6.72 221 85% 7.8-7.9 180 85% 7.3-7.7 160 85% 7.5-7.6 150 85% 7.9 140 85% 7.6-7.7 220 85% 7.7-8.1 210 85% 7.8-8.1 360 85% 7.6-7.8 310 85% 7.5-7.9 330 Species Mean Acute Value (ng/L) Reference Dwyer et al. 1995 221 Brooke 1993a Dwyer et al. 1995 169.7 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 166.6 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 Dwyer et al. 1995 25 ------- Table 1. Acute Toxicity of Nonylphenol to Aquatic Animals (continued) Species Fathead minnow (0.34 + 0.24 g), Pimephales promelas Fathead minnow (0.39 ±0.14 g), Pimephales promelas Fathead minnow (32 d), Pimephales promelas Fathead minnow (25- 35 d), Pimephales promelas Bonytail chub (0.29 ±0.08 g), Gila elegans Bonytail chub (0.52 ±0.09 g), Gila elegans Colorado squawfish (0.32 ±0.05 g), Ptychocheilus lucius Colorado squawfish (0.34 ±0.05 g), Ptychocheilus lucius Razorback sucker (0.31 ±0.04 g), Xyrauchen texanus Razorback sucker (0.32 + 0.07g), Xyrauchen texanus Gila topminnow (0.219 g, 27.2mm), Poeciliopsis occidentalis Method3 S,U s,u F,M F,M S,U S,U S,U S,U S,U s,u s,u Chemical pH 85% 7.5-7.6 85% 7.8-8.2 99% 7.29 >90% 7.23 85% 7.7-7.9 85% 7.4-7.6 85% 8.1-8.2 85% 7.8-8.0 85% 7.8-8.1 85% 7.9-8.0 85% 8.0 LC50 or EC50b Otg/L) 170 290 140 128 270 310 240 270 160 190 230 Species Mean Acute Value (n2/L) Reference Dwyer et al. 1995 Dwyer et al. 1995 Holcombe et al. 1984; University of Wisconsin- Superior 1985 133.9 Brooke 1993a Dwyer et al. 1995 289.3 Dwyeretal. 1995 Dwyer et al. 1995 254.6 Dwyeretal. 1995 Dwyer et al. 1995 174.4 Dwyeretal. 1995 230 Dwyer et al. 1999a 26 ------- Table 1. Acute Toxicity of Nonylphenol to Aquatic Animals (continued) Species Method" Fountain darter (0 . 062 S , U g, 20.2mm), Eiheostoma rub rum Greenthroat darter S,U (0.133 g, 22.6mm), Elheosloma lepidum Bluegill (juvenile), F,M Lepomis macrochirus Boreal toad S,U (0.012 g, 9.6 mm), Bufo boreas Coot clam S,U (embryo/larva), Mulinia lateralis Copepod (10-12 d), S,U Acartia lonsa Mysid ( < 24-hr old), F,M Americamysis bahia Mysid (< 24-hr old), F,M Americamysis bahia Amphipod (adult), F,M Leplocheirus plumulosus Grass shrimp F,M (48-hr old), Palaemonetes vulgaris American lobster (1st R,U stage), Homarus americanus Mud crab F,M fdrh anrl Sth sta?esV Chemical 85% 85% >90% 85% SALTW 90% >95% 90% 90% 90% 90% 90% LCSO or EC^ fig Ug/L) 8.0-8.1 110 8.0-8.2 190 7.61 209 7.9-8.0 120 ATER SPECIES 7.8-8.2 37.9 190 7.3-8.2 43 7.8-8.2 60.6 7.8-8.2 61.6 7.8-8.2 59.4 7.8-8.2 71 7.8-8.2 >195 Species Mean Acute Value 110 190 209 120 37.9 190 51.05 61.6 59.4 71 >195 Reference Dwyer et al. 1999a Dwyer et al. 1999a Brooke 1993a Dwyer et al. 1999a Lussier et al. 2000 Kusk and Wollenberger 1999 Ward and Boeri 1990a Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Dyspanopeus sayii 27 ------- Table 1. Acute Toxicity of Nonylphenol to Aquatic Animals (continued) Species Method3 Winter flounder S,M (48-hr-old), Pleuronectes americanus Sheepshead minnow F,M (juvenile) , Cyprinodon variegatus Sheepshead minnow F,M (juvenile) , Cyprinodon variegatus Inland silversides F,M (juvenile) , Menidia beryllina LCSO or EC50b Chemical pH (jte/L) 90% 7.8-8.2 17 >95% 7.4-8.1 310 90% 7.8-8.2 142 90% 7.8-8.2 70 Species Mean Acute Value (wg/L) Reference 17 Lussier et al. 2000 Ward and Boeri 1990b 209.8 Lussier et al. 2000 70 Lussier et al. 2000 1 S = static; R = renewal; F = flow-through; M = measured; U = unmeasured. b Each Species Mean Acute Value was calculated from the associated underlined number(s) in the preceding column. 28 ------- Table 2a. Chronic Toxicity of Nonylphenol to Aquatic Animals Species Cladoceran, Ceriodaphnia dubia Cladoceran, Daphnia magna Cladoceran, Daphnia magna Cladoceran, Daphnia magna Midge, Chironomus Tentans Rainbow trout, Oncorhynchus mykiss Fathead minnow, Pimephales promelas Mysid, Americamysis bahia Test" LC LC LC LC LC ELS ELS LC Chemical >95% 93.1 >90% 91.8% 95% >90% >95% >95% pH 8.3-8.6 8.04 8.46 8.25 7.73 6.97 7.1-8.2 7.4-8.3 Chronic Limits 88.7-202 10.7-47.8 116-215 24-39 42-91 6.0-10.3 7.4-14 3.9-6.7 Chronic Value 133.9 22.62 157.9 30.59 61.82 7.861 10.18 5.112 Reference England 1995 Fliedner 1993 Brooke 1993a Comber et al. 1993 Kahletal. 1997 Brooke 1993a Ward and Boeri 1991c Ward and Boeri 1991b a LC = life-cycle or partial life-cycle; ELS = early life-stage. b Based upon measured concentrations of nonylphenol. 29 ------- Table 2b. Acute-Chronic Ratios Acute-Chronic Ratios Acute Value Chronic Value Species Cladoceran, Daphnia magna Cladoceran, Daphnia magna Mysid, Americamysis bahia Rainbow trout, Oncorhynchus mykiss pH 7.87-8.46 8.25 7.3-8.3 6.72-6.97 (we/L) 84.8 190 43 221 (we/L) 157.9 30.59 5.112 7.861 Ratio 2.000" 6.211 8.412 28.11 Reference Brooke 1993a Comber et al. 1993 Ward and Boeri 1990a, 1991b Brooke 1993a Acute-Chronic Ratio calculated as 0.5370 but changed to 2.000 (see text). 30 ------- Table 3. Ranked Genus Mean Acute Values with Species Mean Acute-Chronic Ratios Rank8 15 14 13 12 11 10 9 8 denus Mean Acute Value (MB/L) 774 596 342 289.3 254.6 230 209 184.2 Species FRESHWATER SPECIES Snail, Physella virgata Dragonfly, Ophiogomphus sp. Annelid, Lumbriculus variegatus Bony tail chub, Gila elegans Colorado squawfish, Ptychocheilus lucius Gila topminnow, Poeciliopsis occidentalis BluegiU, Lepomis macrochirus Rainbow trout, Oncorhynchus mykiss Apache trout, Oncorhynchus apache Lahontan cutthroat trout, Species Mean Acute Value (Me/L)b 774 596 342 289.3 254.6 230 209 221 169.7 166.6 Species Mean Acute-Chronic Ratioc 28.11 174.4 Oncorhynchus clarki henshawi, and Greenback cutthroat trout, Oncorhynchus clarki stomais Razorback sucker, Xyrauchen texanus 174.4 6 5 4 160 144.6 133.9 Midge, Chironomus tentans Greenthroat darter, Etheostoma lepidwn Fountain darter, Etheostoma rubrum Fathead minnow, 160 190 110 133.9 Pimephales promelas 31 ------- Table 3. Ranked Genus Mean Acute Values with Species Mean Acute-Chronic Ratios (continued) Rank" 3 2 1 10 9 8 7 6 5 4 3 2 1 Genus Mean Acute Value (us./'L) 126.9 120 55.72 209.8 >195 190 71 70 61.6 59.4 51.05 37.9 17 Species Cladoceran, Daphnia magna Boreal toad, Bufo boreas Aruphipod, Hyalella azteca SALTWATER SPECIES Sheepshead minnow, Cyprinodon variegatus Mud crab, Dyspanopeus sayii Copepod, Acartia lonsa American lobster, Homarus americanus Inland silversides, Menidia beryllina Amphipod, Leptocheirus plumulosus Grass shrimp, Palaemonetes vulgaris Mysid, Americarnysis bahia Coot clam, Mulinia lateralis Winter flounder, Pleuronectes americanus Species Mean Acute Value (ue/L)b 126.9 120 55.72 209.8 >195 190 71 70 61.6 59.4 51.05 37.9 17 Species Mean Acute-Chronic Ratioc 3.524 8.412 1 Ranked from the most resistant to the most sensitive based on Genus Mean Acute Value. b From Table 1. c From Table 2. 32 ------- Table 3. Ranked Genus Mean Acute Values with Species Mean Acute-Chronic Ratios (continued) Fresh Water Final Acute Value = 55.71 Criterion Maximum Concentration = 55.71/2 = 27.86 /u.g/L Final Acute-Chronic Ratio = 9.410 (see text) Final Chronic Value = (55.71 //g/L)/9.410 = 5.920 Salt Water Final Acute Value = 13.35 //g/L Criterion Maximum Concentration = 13.35/2 = 6.675 ,ug/L Final Acute-Chronic Ratio = 9.410 (see text) Final Chronic Value = (13.35 ^g/L)/9.410 = 1.419 //g/L 33 ------- Table 4. Toxicity of Nonylphenol to Aquatic Plants Species Chemical Duration (days) Effect Concentration Qug/L) Reference FRESHWATER SPECIES Green algae, Selenastrum capricornutum >95% 7.8 EC50 410 Ward and Boeri 1990a SALTWATER SPECIES Diatom, Skeletonema costatum >95% 30a EC50, number of cells 27 Ward and Boeri 1990d ^Salinity (g/kg). 34 ------- Table 5. Bioaccumulation of Nonylphenol by Aquatic Organisms Cone. in Normalized BCF BCF Species Fathead minnow (0.5-1 g), Pimephales promelas Fathead minnow (0.5-1 g), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Water Duration Percent or Chemical (ug/L)' pH (days) Tissue Lipids BAFb FRESHWATER SPECIES >95% 4.9 7.0-7.6 27 Whole 271 body >95% 22.7 7.0-7.6 27 Whole 344 body 99% 18.4 7.62 4 Whole 4.7 + 1.7 751 body 99% 41.9 7.62 4 Whole 4.7±1.7 677 body 99% 82.1 7.62 4 Whole 4. 7 ±1.7 945 body 99% 9.3 7.60 28 Whole 4.7 + 1.7 769 body 99% 19.2 7.60 28 Whole 4.7±1.7 984 body or BAF Reference Ward and Boeri 1991a Ward and Boeri 1991a 159.8 Brooke 1993b 144.0 Brooke 1993b 201.1 Brooke 1993b 163.6 Brooke 1993b 209.4 Brooke 1993b 35 ------- Table 5. Bioaccumulation of Nonylphenol by Aquatic Organisms (continued) Cone. in Water BCF Duration Percent or Normalized BCF or Species Chemical (Mg/L)a pH Fathead 99% 38.1 7.60 minnow (4-wk old), Pimephales promelas Fathead 99% 77.5 7.60 minnow (4-wk old), Pimephales promelas Fathead 0.4 minnow >98% 1.6 (adult), 3.4 Pimephales promelas Bluegill 99% 21.6 7.79 (4-wk old), Lepomis macrochirus Bluegill 99% 43.9 7.79 (4-wk old), Lepomis macrochirus Bluegill (4-wk old), 99% 86.5 7.79 Lepomis macrochirus Bluegill 99% 5.6 7.55 (4-wk old), Lepomis macrochirus Bluegill 99% 12.4 7.55 (4-wk old), Lepomis macrochirus Bluegill 99% 27.6 7.55 (4-wk old), Lepomis macrochirus (days) Tissue Lipids BAFb 28 Whole 4. 7 ±1.7 876 body 28 Whole 4.7 + 1.7 603 body Whole 203 42 body 252 268 4 Whole 4. 9 ±1.5 279 body 4 Whole 4.9±1.5 257 body 4 Whole 4.9±1.5 223 body 28 Whole 4.911.5 231 body 28 Whole 4.9 + 1.5 253 body 28 Whole 4.911.5 250 body BAF0 Reference 186.4 Brooke 1993b 128.3 Brooke 1993b Giesy et al. 2000 56.94 Brooke 1993b 52.45 Brooke 1993b r 45.51 Brooke 1993b 47.14 Brooke 1993b 51.63 Brooke 1993b 51.02 Brooke 1993b 36 ------- Table 5. Bioaccumulation of Nonylphenol by Aquatic Organisms (continued) Species Bluegill (4-wkold), Lepomis macrochirus Bluegill (juvenile), Lepomis macrochirus Cone. in Water Chemical (^g/L1)' 99% 59.5 1.0 96.4% 3.0 30.0 Duration pH (days) 7.55 28 7.7 20 BCF Percent or Tissue Lipids BAFb Whole 4.9 + 1.5 191 body 76 Whole 0.72 60 body ±0.46 37 Normalized BCF or BAF 38.98 105.6 83.33 51.39 Reference Brooke 1993b Liber et al. 1999 SALTWATER SPECIES Blue mussel, Mytikis edulis Blue mussel, Mytihis edulis Common shrimp, Crangon crangond Common shrimp, Crangon crangond Three-spined stickleback, Gasterosteus aculeatus Three-spined stickleback, Gasterosteus aculeatus 14C- 5.9 labeled UC- 6.2 labeled 14C- 6.4 labeled 14C- 7.4 labeled I4C- 4.8 labeled 14C- 4.9 labeled 16 16 16 16 16 16 Whole 1.6 2,740 body Whole 1.9 4,120 body Whole 1.4 110 body Whole 1.7 900 body Whole 6.7 1,200 body Whole 7.8 1,300 body 1,712 2,168 78.75 529.4 179.1 166.7 Ekelund et al. 1990 Ekelund et al. 1990 Ekelund et al. 1990 Ekelund et al. 1990 Ekelund et al. 1990 Ekelund et al. 1990 1 Measured concentration of nonylphenol. b Bioconcentration factors (BCFs) and bioaccumulation factors (BAFs) are based on measured concentrations of nonylphenol in water and in tissue. c When possible, the factors were normalized to 1 % lipids by dividing the BCFs and BAFs by the percent lipids. d Non-resident species. 37 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms Species Chemical Duration Effect Concentration Cug/L) Reference _ -I Green alga, Chlamydomonas reinhardtii Floating moss, Salvinia molesta Duckweed, Lemna minor Duckweed, Lemna minor Ciliate protozoan, Tetrahymena pyriformis Ciliate protozoan, Tetrahymena pyriformis Rotifer (4 to 6 hr-old female) Brachionus calydflorus Clam (15 g), Anodonta cataractae Zooplankton Benthic macro- invertebrates Cladoceran (< 24-hr old), Daphnia magna Cladoceran (< 24-hr old and FRESHWATER 24 days 9 days 5.6 96 hr 4 days 24 hr 7.40 40 hr Technical 7.5 96 hr 144 hr 96.4% 7.5 8.2 20 days 96.4% 7.5 8.2 20 days 8.0 21 days '85% 7.8 8.4 96 hr (fed) SPECIES 100% algistatic Reduced frond production IC50 Reduced frond production EC50 Reduced population growth 50% Sexual reproduction reduced LC50 NOEC LOEC NOEC LOEC NOEC LOEC (reduced fecundity) MATC (young) MATC (adults) 6,250 2,500 5,500 125 460 747 50 5000 23 76 23 76 50 100 302 136 Weinberger and Greenhalgh 1984 Prasad 1986 . Weinberger and lyengar 1983 Prasad 1986 Yoshioka 1985 Schultz 1997 Preston et al. 2000 McLeese et al. 1980b O'Halloran et al. 1999 Schmude et al. 1999 Baldwin et al. 1997 Gerritsen et al. 1998 adults), Daphnia magna 38 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Cladoceran (< 24-hr old), Daphnia magna Cladoceran (< 24-hr old), Daphnia magna Cladoceran (< 36-hr old), Daphnia galeata mendolae Cladoceran (> 48-hr old), Daphnia pulex Cladoceran (> 48-hr old), Daphnia pulex Cladoceran (> 48-hr old), Daphnia pulex Cladoceran (< 24-hr old), Ceriodaphnia dubia Cladoceran (< 24-hr old), Ceriodaphnia dubia Midge (2nd instar) , Chironomus tentans Sea lamprey (larva), Petromyzon marinus Chemical pH Duration "85% 7.7 + 0.02 21 days Technical 21 days 30 days Practical 48 hr grade Practical 48 hr grade Practical 48 hr grade >95% 8.3-8.6 48 hr >95% 8.3-8.6 7 days >95% 8.2 14 days 7.5-8.2 14 hr Effect No sex ratio change (high food rate) Increased ratio of males (low food rate) 50% adult mortality NOEC (deformed offspring) NOEC LOEC (deformed offspring) LC50 LC50 LC50 LC50 (fed) LC50 (fed) LC50 EC50 LT100 (UE/D 25 25 200.5 44 10 50- 140 176 190 276 225 119 95 5,000 Reference Baer and Owens 1999 LeBlanc et al. 2000 Shurin and Dodson 1997 Ernst etal. 1980 Ernst et al. 1980 Ernst et al. 1980 England 1995 England 1995 England and Bussard 1993 Applegate et al. 1957 39 ------- IF Table 6. Other Data on Effects of Nonylpheuol on Aquatic Organisms (continued) Species Brook trout (juvenile), Salvelinus fontinalis Lake trout (juvenile), Salvelinus naymaycush Brown trout (fmgerling), Salmo iruua Atlantic salmon (4g), Salmo salar Chinook salmon (juvenile), Oncorhynchus tshawytscha Coho salmon (juvenile), Oncorhynchus kisutch Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (juvenile), Oncorhynchus mykiss Chemical Practical grade Practical grade oH Duration 96 hr 35 days 7.0 7.2 7.2 2hr 96 hr 3hr 3hr 7.5-8.2 4hr 96hr 96 hr 96 hr Effect LC50 LC50 (fed) LT100 LC50 LT100 LT100 LT100 LC50 LC50 LC50 Concentration (ug/L) Reference 145 Holmes and Kingsbury 1980 > 40 Holmes and Kingsbury 1980 5,000 Wood 1953 900 McLeese et al. 1980b 10,000 MacPhee and Ruelle 1969 10,000 MacPhee and Ruelle 1969 5,000 Applegate et al. 1957 920 Ernst et al, 1980 560 Ernst et al. 1980 230 Holmes and Kingsbury 1980 40 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Chemical Rainbow trout (adult males), Oncorhynchus mykiss Rainbow trout (adult males), Oncorhynchus mykiss Rainbow trout (50-200g), Oncorhynchus mykiss Rainbow trout (50 200 g), Oncorhynchus mykiss Rainbow trout, (40 - 60 g), Oncorhynchus mykiss Rainbow trout (40 - 60 g), Oncorhynchus mykiss Rainbow trout (40 - 60 g), Oncorhynchus mykiss Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (? juvenile), Oncorhynchus mykiss >99% >99% >99% 6.5 Concentration Duration 3 wk 3 wk 72 hr 72 hr 8hr 2-5hr 12 - 24 hr 4hr 72 hr 22 days 35 days Effect (w£/L) Increased 20.3 vitellogenin production Increased 54.3 vitellogenin production LC50 193.65 Increased 14.14 vitellogenin mRNA Tissue half-life 18 fat 19.8hr muscle 1 8 . 6 hr liver 5. 9 hr Eviscerated 1 8 carcass BAF = 24.21 Viscera 18 BAF = 98.2 Vitellogenin 10 mRNA production Vitellogenin 100 production Reduced growth 50 at 108 days Reduced growth 30 at 466 days Reference Jobling et 1996 Jobling et 1996 Lech et al. Lech et al. Lewis and 1996 Lewis and 1996 Lewis and 1996 Ren et al. Ren et al. al. al. 1996 1996 Lech Lech Lech 1996a 1996b Ashfield et al. 1998 41 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Rainbow trout (juvenile), Oncorhynchus mykiss Rainbow trout (35-50 g, immature), Oncorhynchus mykiss Rainbow trout (adult males), Oncorhynchus mykiss Rainbow trout (juvenile, 103- 168 g), Oncorhynchus mykiss Rainbow trout (adult males) , Oncorhynchus mykiss Rainbow trout (598 g; juvenile females), Oncorhynchus mykiss Chemical pH Duration Effect Cug/L) 96 hr Decreased 220 number of muscarinic cholinergic receptors in brain 8.0 - 8.4 21 days Increased 50 vitellogenin in blood plasma 3 wk BCF = 116 63 BCF = 88 81 99% 9 days No vitellogenin 109 induction Technical 10 days Epidermal 1 per month mucous cell for 4 granulation months 99% 18 wk Reduced GSI; 85.6 Reduced HSI; 85.6 Induced 8 . 3 vitellogenin; Lowered plasma 85.6 estradiol; Lowered plasma 8.3 FSH Reference Jones et al. 1998 Tremblay and Van Der Kraak 1998 Blackburn et al. 1999 Pedersen et al. 1999 Burkhardt-Holm et al. 2000 Harris et al. 2001 42 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Rainbow trout (1667 +201.6 g; F0 3 yr-old adults), Oncorhynchus mykiss Lahontan cutthroat trout (juvenile), Oncorhynchus clarki henshawi Apache trout (juvenile), Oncorhynchus mykiss Northern squawfish (juvenile), Ptychocheilus oregonensis Colorado squawfish (juvenile), Ptychocheilus lucius Goldfish (juvenile), Carassius auratus Concentration Chemical pH Duration Effect (ME/L) 98% 7.6 4 months Reduced embryo 1 (exposed 10 survival; days/month) Reduced hatch; 10 F0 Males 1 increased vitellogenin; Fj Females 10 increased vitellogenin and testosterone; F! Males 10 increased estradiol 96 hr Decreased 220 number of muscarinic cholinergic receptors in brain 96 hr Decreased > 130 number of muscarinic cholinergic receptors in brain Reference Schwaiger et al. 2002 Jones etal. 1998 Jones et al. 1998 7.2 3hr LT100 96 hr 7.0 5hr Decreased number of muscarinic cholinergic receptors in brain LT100 10,000 >220 MacPhee and Ruelle 1969 Jones et al. 1998 5,000 Wood 1953 43 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Species Common carp (15.2 +3.8g juvenile), Cyprinus carpio Common carp (50-150 g mature males), Cyprinus carpio Fathead minnow (4-wk old), Pimephales promelas Fathead minnow (4-wk old), Pimephales promelas Fathead minnow, Pimephales promelas Fathead minnow (mature), Pimephales promelas Fathead minnow (mature), Pimephales promelas Fathead minnow (mature), Pimephales promelas Fathead minnow (mature), Pimephales promelas Chemical Technical (90% 4-NP) 95% 99% 99% >98% >98% >98% >98% pH Duration 7.6 70 days 7.57 28-31 +0.03 days 11 °C 7.62 4 days 7.60 28 days 96 hr 42 days 42 days 42 days 42 days Effect Decreased erythrocytes; Increased reticulocytes BCF = 546.5 No change in ivp-estradiol, testosterone, or vitellogenin LC50 (fed) BCF = 100.4 Decreased number of muscarinic cholinergic receptors hi brain Possible increased number of Sertoli cells in males Decreased fecundity Increased d" vitellogenin Increased 17p-estradiol Concentration Cug/L) Reference 10 Schwaiger et al. 2000 10 5.36 Villenueve et al. 2002 138 Brooke 1993b 193 Brooke 1993b > 220 Jones et al. 1998 1.6 Miles- Richardson et al. 1999 >0.4 Giesyetal. 2000 >3.4 Giesyetal. 2000 >0.05 Giesyetal. 2000 44 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Chemical pH BluegiU 7.0 (juvenile), Lepomis macrochirus BluegiU 7.5-8.2 (juvenile), Lepomis macrochirus Bluegill 99% 7.79 (4-wk old), Lepomis macrochirus Bluegffl 99% 7.55 (4-wk old), Lepomis macrochirus BluegiU 96.4% 7.7 7.9 (juvenile), Lepomis macrochirus Southern Technical platyfish (adult, 85 % 0.62 to 1.15g), Xiphophorus maculatus Green Swordtail Technical (adult males), Xiphophorus helleri Green Swordtail Technical (juvenile 30-d-old males), Xiphophorus helleri African clawed ACS Grade 7.8 - 8.0 frog (larva), Xenopus laevis Duration 2hr 14 hr 4 days 28 days 20 days 28 days 96 hr 72 hr 60 days 21 days Effect CUE/L) LT100 5,000 LT100 5,000 LC50 135 (fed) BCF = 35.31 126 NOEC 76 LOEC (survival) 243 Reduced GSI 960 LC50 206 ViteUogenin 4 induced Reduced sword 0.2 length NOEC 25 LOEC 50 (increased rate of tail resorption) Reference Wood 1953 Applegate et al. 1957 Brooke 1993b Brooke 1993b Liber et al. 1999 Kinnberg et al. 2000 Kwak et al. 2001 Kwak et al. 2001 Fort and Stover 1997 45 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Chemical African clawed frog (larva), Xenopus laevis Red alga, >95% Champia parvula Barnacle (cypris larva), Balanus amphitrite Soft-shell clam, Mya arenaria Coot clam, 90% Mulinia lateralis Coot clam, 90% Mulinia lateralis Coot clam, 90% Mulinia lateralis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis Blue mussel, Mytilus edulis pH Duration 12 wk SALTWATER 2 days 48 hr 360 hr 30-311 24 hr 30-3 r 48 hr 30-3 la 72 hr 32a 96 hr 32a 360 hr 32a 13 days 32a 30 days 32a 30 days 32a 32 days 32a 24 hr Effect Increased female phenotypes SPECIES No effect on sexual reproduction Reduced cyprid settlement No mortality LC50 LC50 LC50 LC50 LC50 Reduced byssus strength Reduced byssus strength No byssus threads formed Reduction in growth No effect on fertilization Oig/L) 22 167 1.0 700 -50 -50 -40 3,000 500 56 56 100 56 200 Reference Kloas et al. 1999 Tagliabue 199: Billinghurst et al. 1998 McLeese et al. 1980b Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Granmo et al. 1989 Granmo et al. 1989 Granmo et al. 1989 Granmo et al. 1989 Granmo et al. 1989 Granmo et al. 1989 Granmo et al. 1989 46 ------- Table 6. Other Data on Effects Species Chemical Blue mussel, Mytilus edulis Blue mussel (40-50 mm length), Mytilus edulis Blue mussel, Mytilus edulis galloprovincialis Mysid, 90% Americamysis bahia Mysid, 90% Americamysis bahia Mysid, 90% Americamysis bahia Mysid, 90% Americamysis bahia Mysid, 90% Americamysis bahia Mysid, 90% Americamysis bahia Mysid, >95% Americamysis bahia Mysid, >95% Americamysis bahia Mysid, >95% Americamysis bahia Copepod (10-12 d), Acartia tonsa of Nonylphenol on Aquatic Organisms (continued) pH Duration Effect 32a 72 hr No effect on development 50 days BCF = 350 2 days Repelled attachment 30-3 r 24 hr LC50 30-3 la 48 hr LC50 30-3 la 72 hr LC50 30-3 la 120 hr LC50 30-3 la 144 hr LC50 30-31* 168hr LC50 20a 24 hr LC50 20a 48 hr LC50 20a 72 hr LC50 18a 48 hr LC50 synthetic media Concentration (we/L) 200 40 22 -114 -82 -66 -60 -60 -60 >47 >47 44 360 280 Reference Granmo et al. 1989 Granmo et al. 1991a,b Etoh et al. 199 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Ward and Boei 1990a Ward and Boei 1990a Ward and Boei 1990a Kusk and Wollenberger 1999 47 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Amphipod, Lepiocheirus plumulosus Amphipod, Leptocheirus plumulosus Amphipod, Leptocheirus plumulosus Amphipod, Leptocheirus plumulosus Amphipod, Leptocheirus plumulosus Grass shrimp, Palaemonetes vulgaris Grass shrimp, Palaemonetes vulgaris Grass shrimp, Palaemonetes vulgaris Grass shrimp, Palaemonetes vulgaris Shrimp, Crangon septemspinosa Shrimp, Crangon septemspinosa Shrimp, Crangon septemspinosa American lobster, Homarus americanus Chemical 90% 90% 90% 90% 90% 90% 90% 90% 90% >95% >95% >95% 90% pH Duration 30-31a 48 hr 30-312 72 hr 30-3 r 120 hr 30-31a 144 hr 30-3 la 168 hr 30-3 la 24 hr 30-313 48 hr 30-3 la 72 hr 30-31a 120 hr 96 hr 96 hr 96 hr 30-3 la 24 hr Effect LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 (we/L) -160 -80 -50 -40 -30 -125 -60 -60 -60 300 300 300 -140 Reference Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 2000 McLeese et al. 1980b McLeese et al. 1980b McLeese et al. 1980b Lussier et al. 2000 48 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Chemical pH Duration American lobster, 90% 30-313 48 hr Homarus americanus American lobster, 90% 30-31* 72 hr Homarus americanus American lobster, > 95 % 96 hr Homarus americanus Atlantic salmon, - 96 hr Salmo salar Atlantic salmon, 96 hr Salmo salar Atlantic salmon, 96 hr Salmo salar Atlantic salmon, 96 hr Salmo salar Sheepshead 90% 30-3 la 72 hr minnow, Cyprinodon variegatus Sheepshead 90% 30-3 11 120 hr minnow, Cyprinodon variegatus Sheepshead 90% 30-3 la 144 hr minnow, Cyprinodon variegatus Sheepshead 90% 30-31" 168 hr minnow, Cyprinodon variegatus Sheepshead >95% 15-17* 24 hr minnow, Cyprinodon variegatus Effect LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 LC50 (uzlU -140 -100 170 190 160 130 900 -150 -125 -120 -120 >420 Reference Lussier et al. 2000 Lussier et al. 2000 McLeese et al. 1980b McLeese et al. 1980b McLeese et al. 1980b McLeese et al. 1980b McLeese et al. 1980b Lussier et al. 2000 Lussier et al. 2000 Lussier et al. 9OOO Z-VJUVJ Lussier et al. 9000 ^-\j\j\j Ward and Boeri 1990c 49 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Concentration Species Sheepshead minnow , Cyprinodon variegatus Sheepshead minnow, Cyprinodon variegatus Killifish (embryo) , Fundulus hetewclitus Killifish (embryo) , Fundulus hetewclitus Killifish (1-day old larva), Fundulus hetewclitus KiUifish (14-day .old larva) , . Fundulus hetewclitus KiUifish (28-day old larva), Fundulus hetewclitus Three spine stickleback Gastewsteus aculeatus Inland silversides, Menidia beryllina Inland silversides, Chemical pH >95% 15-17a >95% 15-17" 85 - 90% 20a (technical) 85-90% 20a (technical) 85-90% 20a (technical) 85 - 90% 20a (technical) . 85-90% 20a (technical) Commercial 32a (para- substituted with branched nonyl chain) 90% 30-3 T 90% 30-3 la Duration Effect 48 hr LC50 72 hr LC50 10 days 100% abnormal development 96 hr LC50 96 hr LC50 (fed) 96 hr LC50 -- (fed) 96 hr LC50 (fed) 96 hr LC50 24 hr LC50 48 hr LC50 Cug/L) Reference 340 Ward and Boeri 1990c 320 Ward and Boeri 1990c 2,204 Kelly and Di Giulio 2000 5,444 Kelly and Di Giulio 2000 214 Kelly and Di Giulio 2000 209 Kelly and Di ... Giulio 2000 260 Kelly and Di Giulio 2000 370 Granmo et al. 1991a -120 Lussier et al, 2000 -100 Lussier et al. 2000 Menidia beryllina 50 ------- Table 6. Other Data on Effects of Nonylphenol on Aquatic Organisms (continued) Species Inland silversides, Menidia beryllina Inland silversides, Menidia beryllina Inland silversides, Menidia beryllina Inland silversides, Menidia beryllina Chemical 90% pH 30-31' Duration 72 hi 90% 30-31° 120 hr 90% 30-31' 144 hr 90% 30-31a 168 hr Effect LC50 LC50 LC50 LC50 Concentration Cug/L) Reference -80 Lussier et al. 2000 -60 Lussier et al. 2000 -60 Lussier et al. 2000 -60 Lussier et al. 2000 Salinity (g/kg). 51 ------- a IF REFERENCES Ahel, M. and W. Giger. 1993. Aqueous solubility of alkylphenols and alkylphenol polyethoxylates. Chemosphere 26:1461-1470. Ahel, M., J. McEvoy and W. Giger. 1993. Bioaccumulation of the lipophilic metabolites of nonionic surfactants in freshwater organisms. Environ. Pollut. 79:243-248. Ahel, M., W. Giger and M. Koch. 1994a. Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment-I. Occurrence and transformation in sewage treatment. Wat. Res. 28:1131-1142. Ahel, M., W. Giger and C. Schaffner. 1994b. Behavior of alkylphenol polyethoxylate surfactants in the aquatic environment-II. Occurrence and transformation in rivers. Wat. Res. 28:1143-1152. Ahel, M., F.E. Scully, Jr., J. Hoigne and W. Giger. 1994c. Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters. Chemosphere 28:1361-1368. Ahel, M., C. Schaffner and W. Giger. 1996. Behaviour of alkylphenol polyethoxylates surfactants in the aquatic environment-Ill.- Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater. Wat. Res. 30:37-46. Ahel, M., E. Molnar, S. Ibric and W. Giger. 2000. Estrogenic metabolites of alkylphenol polyethoxylates in secondary sewage effluents and rivers. Wat. Sci. Technol. 42:15-22. Allen, Y., A.P. Scott, P. Matthiessen, S. Haworth, J.E. Thain and S. Feist. 1999. Survey of estrogenic activity in United Kingdom estuarine and coastal waters and its effects on gonadal development of the flounder Platichthys flesus. Environ. Toxicol. Chem. 18:1791-1800. 52 ------- Amato, J.R. and D.D. Wayment. 1998. Surfactant toxicity identification with a municipal wastewater. In: Environmental Toxicology and Risk Assessment. Little, E.S., A.J. DeLoney and B.M. Greenberg, Eds. ASTM STP 1333, Vol. 7, American Society for Testing and Materials, Philadelphia, PA. pp. 272-283. Andersen, H.R., A. Andersson, S.F. Arnold, H. Autrup, M. Barfoed, N.A. Beresford, P. Bjerregaard, L.B. Christiansen, B. Gissel, R. Hummel, E.B. Jorgensen, B. Korsgaard, R. Le Guevel, H. Leffers, J. McLachlan, A. Moller, J.B. Nielsen, N. Olea, A. Oles-Karasko, F. Pakdel, K.L. Pedersen, P. Perez, N.E. Skakkeboek, C. Sonnenschein, A.M. Soto, J.P. Sumpter, S.M. Thorpe and P. Grandjean. 1999. Comparison of short-term estrogenicity tests for identification of hormone- disrupting chemicals. Environ. Health Perspect. 107(Suppl. 1):89-108. Applegate, V.C., J.H. Howell, A.E. Hall, Jr. and M.A. Smith. 1957. Toxicity of 4,346 chemicals to larval lampreys and fishes. Special Scientific Report-Fisheries, No. 207, U.S. Dept. Interior, Fish and Wildlife Service, Washington, DC. 157pp. Arukwe, A., T. Celius, B.T. Walther and A. Goksoyr. 1998. Plasma levels of vitellogenin and eggshell zona radiata proteins in 4-nonylphenol and o,p' nonylphenol treated juvenile Atlantic salmon (Salmo solar). Mar. Environ. Res. 46:133-136. Arukwe, A., L. Forlin and A. Goksoyr. 1997a. Xenobiotic and steroid biotransformation enzymes in Atlantic salmon (Salmo salar) liver treated with an estrogenic compound, 4-nonylphenol. Environ. Toxicol. Chem. 16:2576-2583. Arukwe, A., F.R. Knudsen and A. Goksoyr. 1997b. Fish zona radiata (eggshell) protein: A sensitive biomarker for environmental estrogens. Environ. Health Perspect. 105:418-422. Arukwe, A., R. Thibaut, K. Ingebrigtsen, T. Celius, A. Goksoyr and J-P. Cravedi. 2000. In vivo and in vitro metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar). Aquat. Toxicol. 49:289-304. 53 ------- AsMield, L.A., T.G. Pottinger and J.P. Sumpter. 1998. Exposure of female juvenile rainbow trout to alkylphenolic compounds results in modifications to growth and ovosomatic index. Environ. Toxicol. Chem. 17:679-686. Baer, K.N. and K.D. Owens. 1999. Evaluation of selected endocrine disrupting compounds on sex determination in Daphnia magna using reduced photoperiod and different feeding rates. Bull. Environ. Contain. Toxicol. 62:214-221. Baldwin, W.S., S.E. Graham, D. Shea and G.A. LeBlanc. 1997. Metabolic androgenization of female Daphnia magna by the xenoestrogen 4-nonylphenol. Environ. Toxicol. Chem. 16:1905-1911. Baldwin, W.S., S.E. Graham, D. Shea and G.A. Leblanc. 1998. Altered metabolic elimination of testosterone and associated toxicity following exposure to Daphnia magna to nonylphenol polyethoxylate. Ecotoxicol. Environ. Saf. 39:104-111. Bearden, A.P. and T.W. Schultz. 1997. Structure-activity relationships for Pimephales and Tetrahymena: a mechanism of action approach. Environ. Toxicol. Chem. 16:1311-1317. Bearden, A.P. and T.W. Schultz. 1998. Comparison of Tetrahymena and Pimephales toxicity based on mechanism of action. SAR QSAR Environ. Res. 9:127-153. Bennett, E.R. and C.D. Metcalfe. 1998. Distribution of alkylphenol compounds in Great Lakes sediments, United States and Canada. Environ. Toxicol. Chem. 17:1230-1235. Bennet, E.R. and C.D. Metcalfe. 2000. Distribution of degradation products of alkylphenol ethoxylates near sewage treatment plants in the Lower Great Lakes, North America.. Environ. Toxicol. Chem. 19: 784-792. Bennie, D.T. 1999. Review of the environmental occurrence of alkylphenols and alkylphenol ethoxylates. Wat. Qual. Res. J. Can. 34:79-122. 54 ------- Bennie, D.T., C.A. Sullivan, H. Lee, I.E. Peart and RJ. Maguire. 1997. Occurrence of alkylphenols and alkylphenol mono- and di-ethoxylates in natural waters of the Laurentian Great Lakes basin and the upper St. Lawrence River. Sci. Total Environ. 193:263-275. Billinghurst, Z., A.S. Clare, T. Fileman, M. McEvoy, J. Readman and M.H. Depledge. 1998. Inhibition of barnacle settlement by the environmental oestrogen 4-nonylphenol and the natural oestrogen 170 oestradiol. Mar. Pollut. Bull. 36:833-839. Blackburn, M.A., S.J. Kirby and M.J. Waldock. 1999. Concentrations of alkyphenol polyethoxylates entering UK estuaries. Mar. Pollut. Bull. 38:109-118. Braaten, B., A. Granmo and R. Lange. 1972. Tissue-swelling in Mytilus edulis L. induced by exposure to a nonionic surface active agent. Norw. J. Zool. 20:137-140. Brooke, L.T. 1993a. Acute and chronic toxicity of nonylphenol to ten species of aquatic organisms. Report to the U.S. EPA for Work Assignment No. 02 of Contract No. 68-C1-0034. Lake Superior Research Institute, University of Wisconsin-Superior, Superior, WI. March 24. 30 pp. Brooke, L.T. 1993b. Accumulation and lethality for two freshwater fishes (fathead minnow and bluegill) to nonylphenol. Report to the U.S. EPA for Work Assignment No. 1-12 of Contract No. 68- Cl-0034. Lake Superior Research Institute, University of Wisconsin-Superior, Superior, WI. September 30. 49 pp. Brooke, L.T. 1994. Accumulation and lethality for two freshwater fishes (fathead minnow and bluegill) to nonylphenol. Report to the U.S. EPA for Work Assignment No. 1-15 of Contract No. 68- Cl-0034. Lake Superior Research Institute, University of Wisconsin-Superior, Superior, WI. May 31. 49pp. Budavari, S. (Ed.). 1989. The Merck Index: An encyclopedia of chemicals, drugs, and biologicals. llth ed. Merck and Co., Inc. Rahway, NJ. 55 ------- Burkhardt-Holm, P., T. Wahli and W. Meier. 2000. Nonylphenol affects the granulation of pattern of epidermal mucous cells in rainbow trout, Oncorhynchus mykiss. Ecotoxicol. Environ. Safe. 46:34-40. Celius, T., T.B. Haugen, T. Grotmol and B.T. Walther. 1999. A sensitive zonagenetic assay for rapid in vitro assessment of estrogenic potency of xenobiotics and mycotoxins. Environ. Health Perspect. 107:63-68. Christiansen, T., B. Korsgaard and A. Jespersen. 1998a. Effects of nonylphenol and 17 p-estradiol on vitellogenin synthesis, testicular structure and cytology in male eelpout Zoarces viviparus. J. Exp. Biol. 201:179-192. Christiansen, T., B. Korsgaard and A. Jespersen. 1998b. Induction of vitellogenin synthesis by nonylphenol and 17p-estradiol and effects on the testicular structure in the eelpout Zoarces viviparus. Mar. Environ. Res. 46:141-144. Christiansen, T., K.L. Pedersen, B. Korsgaard and P Bjerregaard. 1998c. Estrogenicity of xenobiotics in rainbow trout (Oncorhynchus mykiss} using in vivo synthesis of vitellogenin as a biomarker. Mar. Environ. Res. 46(1-5): 137-140. Coldham, N.G., M.J. Sauer, S. Sivapathasundaram, L. Ashfield, T. Pottinger and C. Goodall. 1997. Tissue distribution, metabolism and excretion of 4-nonylphenol in rainbow trout. J. Vet. Pharmacol. Therap. 20(Suppl. 1): 256-257. Coldham, N.G., S. Sivapathasundaram, M. Dave, L.A. Ashfield, T.G. Pottinger, C. Goodall and M.J. Sauer. 1998. Biotransformation, tissue distribution, and persistence of 4-nonylphenol residues in juvenile rainbow trout (Oncorhynchus mykiss). Drug Metabol. Dispos. 26:347-354. Comber, M.H.I., T.D. Williams and K.M. Stewart. 1993. The effects of nonylphenol on Daphnia magna. Wat. Res. 27:273-276. 56 ------- Dorn, P.B., J.P. Salanitro, S.H. Evans and L. Kravetz. 1993. Assessing the aquatic hazard of some branched and linear nonionic surfactants by biodegradation and toxicity. Environ. Toxicol. Chem. 12:1751-1762. Dwyer, F.J., L.C. Sappington, D.R. Buckler and S.B. Jones. 1995. Use of surrogate species in assessing contaminant risk to endangered and threatened species. EPA/600/R-96/029. National Technical Information Service, Springfield, VA. 71 pp. Dwyer, F.J., O.K. Hardesty, C.E. Henke, C.G. Ingersoll, D.W. Whites, D.R. Mount and C.M. Bridges. 1999a. Assessing contaminant sensitivity of endandered and threatened species: Toxicant classes. EPA/600/R-99/098. National Technical Information Service, Springfield, VA. 15pp. Dwyer, F.J., O.K. Hardesty, C.E. Henke, C.G. Ingersoll, D.W. Whites, D.R. Mount and C.M. Bridges. 1999b. Assessing contaminant sensitivity of endangered and threatened species: Effluent toxicity tests. EPA/600/R-99/099. National Technical Information Service, Springfield, VA. 9 pp. Ekelund, R., A. Bergman, A. Granmo, and M. Berggren. 1990. Bioaccumulation of 4-nonylphenol in marine animals—A re-evaluation. Environ. Poll. 64: 107-120. Ekelund, R., A. Granmo, K. Magnusson and M. Berggren. 1993. Biodegradation of 4-nonylphenol in seawater and sediment. Environ. Pollut. 79:59-61. Ellis, D.D., C.M. Jone, R.A. Larson and D.J. Schaeffer. 1982. Organic constituents of mutagenic secondary effluents from wastewater treatment plants. Arch. Environ. Contain. Toxicol. 11:373-382. England, D.E. 1995. Chronic toxicity of nonylphenol to Ceriodaphnia dubia. Report No. 41756. ABC Laboratories, Inc. Columbia, MO. 409 pp. England, D.E. and J.B. Bussard. 1993. Toxicity of nonylphenol to the midge Chironomus Unions. Report No. 40597. ABC Laboratories, Inc., Columbia, MO. 2528 pp. 57 ------- England, D.E. and J.B. Bussard. 1995. Toxicity of nonylphenol to the amphipod Hyalella azteca. Report No. 41569. ABC Laboratories, Inc., Columbia, MO. 178 pp. Ernst, B., G. Mien, K. Doe and R. Parker. 1980. Environmental investigations of the 1980 spruce budworm spray program in New Brunswick. Surveillance Report EPS-5-AR-81-3, November 1980. Environment Canada, Atlantic Region, Halifax, NS. Escher, M., T. Wahli, S. Buttner, W. Meier and P. Burkhardt-Holm. 1999. The effect of sewage plant effluent on brown trout (Salmo trutta fario): a cage experiment. Aquat. Sci. 61:93-110. Etoh, H., S. Hageshita and K. Ina. 1997. An improved assay for attachment-promoting substances of the blue mussel, Mytilus edulis galloprovincialis. J. Mar. Biotechnol. 5:24-26. Fay, A.A., F.J. Brownawell, A.A. Elskus and A.E. McElroy. 2000. Critical body residues in the marine amphipod Ampelisca abdita: Sediment exposures with nonionic organic contaminants. Environ. Toxicol. Chem. 19:1028-1035. Federal Register. 1990. Testing consent order on 4-nonylphenol, branched. Vol. 55, No. 35, Wednesday February 21.. pp. 5991-5994. Fliedner, A. 1993. Daphnia magna, Reproduction test (OECD No. 202). Fraunhofer-Institute fur Umweltchemie und Okotoxikologie, Postfach 1260, W-5948 Schmallenberg - Grafschaft, Germany. Report No. UBA-002/4-22 February. Flouriot, G., F. Pakdel, B. Ducouret and Y. Valotaire. 1995. Influence of xenobiotics on rainbow trout liver estrogen receptor and vitellogenin gene expression. J. Molecular Endocrin. 15:143-151. Folmar, L., M. Hemmer, N. Denslow, K. Kroll, A. Cheek, H. Meredith, H. Richman and G. Grau. 1998. A comparison of an in vivo fish VTG assay with YES and E-screen to rank 'relative estrogenicity' of natural pharmaceutical and xenoestrogens. Am. Zool. 38:112A. 58 ------- Fort, D.J. and E.L. Stover. 1997. Development of short-term, whole-embryo assays to evaluate detrimental effects on amphibian limb development and metamorphosis using Xenopus laevis. In: Environmental Toxicology and Risk Assessment: Modeling and Risk Assessment. F.J. Dwyer, T.R. Doane and M:L. Hinman (Eds.). ASTM, STP 1317, Vol. 6, American Society for Testing and Materials, Philadelphia, PA., pp. 376-390. Gaffney, P.E. 1976. Carpet and rug industry case study II: Biological effects. J. Water Pollut. Control Fed. 48:2731-2737. Gerritsen, A., N. van der Hoeven and A. Pielaat. 1998. The acute toxicity of selected alkylphenols to young and adult Daphnia magna. Ecotoxicol. Environ. Safety. 39:227-232. Giesy, J.P., S.L. Pierens, E.M. Snyder, S. Miles-Richardson, V.J. Kramer, S.A. Snyder, K.M. Nichols and D.A. Villeneuve. 2000. Effects of 4-nonylphenol on fecundity of biomarkers of estrogenicity in fathead minnows (Pimephalespromelas). Environ. Toxicol. Chem. 19:1368-1377. Giger, W., E. Stephanou and C. Schafmer. 1981. Persistent organic chemicals in sewage effluents: I. Identifications of nonylphenols and nonylphenol ethoxylates by glass capillary gas chromatography/ mass spectrometry. Chemosphere 10:1253-1263. Giger, W., P.H. Brunner and C. Schaffner. 1984. 4-Nonylphenol in sewage sludge; Accumulation of toxic metabolites from nonionic surfactants. Science 225:623-625. Granmo, A., R. Ekelund, K. Magnusson and M. Berggren. 1989. Lethal and sublethal toxicity of 4-nonylphenol to the common mussel (Mytilus edulis L.). Environ. Poll. 59: 115-127 Granmo, A., R. Ekelund, M. Berggren and K. Magnusson. 1991a. Toxicity of 4-nonylphenol to aquatic organisms and potential for bioaccumulation. Proceedings, Swedish Environmental Protection Agency Seminar on Nonylphenol Ethoxylates/nonylphenol, Saltsjobaden, Sweden, February 6-8, pp. 53-75. 59 ------- Granmo, A., S. Kollberg, M. Berggren, R: Ekelund, K. Magnusson, L. Renberg and C. Wahlberg. 1991b. Bioaccumulation of nonylphenol in caged mussels in an industrial coastal area on the Swedish west coast. In: Organic Micropollutants in the Aquatic Environment. Angeletti, G. (Ed.). Proceedings of the 6th European Symposium, pp 71-79. Gray, M.A. and C.D. Metcalfe. 1997. Induction of testis-ova in Japanese medaka (Oryzias latipes) exposed to p-nonylphenol. Environ. Toxicol. Chem. 16:1082-1086. Hale, R.C., C.L. Smith, P.O. de Fur, E. Harvey, E.O. Bush, M.J. La Guardia and G.G. Vadas. 2000. Nonylphenols in sediments and effluents associated with diverse wastewater outfalls. Environ. Toxicol. Chem. 19:946-952. Hansen, F.T., V.E. Forbes and T.L. Forbes. 1999. Effects of 4-n-nonylphenol on life-history traits and population dynamics of a polychaete. Ecol. Appl. 9:482-495. Hansen, P., H. Dizer, B. Hock, A. Marx, J. Sherry, M. McMaster and C. Blaise. 1998. Vitellogenin - a biomarker for endocrine disruptors. Trends Anal. Chem. 17:448-451. Harries, I.E., D.A. Sheahan, S. Jobling, P. Matthiessen, P. Neall, J.P. Sumpter, T. Tylor and N. Zaman. 1997. Estrogenic activity in five United Kingdom rivers detected by measurement of vitellogenesis in caged male trout. Environ. Toxicol. Chem. 16:534-542. Harris, C.A., E.M. Santos, A Janbakhsh, T.G. Pottinger, C.R. Tyler and J.P. Sumpter. 2001. Nonylphenol affects gonadotropin levels in the pituitary gland and plasma of female rainbow trout. Environ. Sci. Technol. 35:2909-2916. Harvilicz, H. 1999. NPE demand remains strong despite environmental concerns in Europe. Chemical Market Reporter. October 18, 1999. p. 15. 60 ------- Haya, K., L.E. Burridge and T.J. Benfey. 1997. The effect of cortisol and nonylphenol on growth and ornithine decarboxylase activity of juvenile Atlantic salmon, Salmo salar Can. Tech. Rep. Fish. Aquat. Sci. 2192: 85-86. Heinis, L.J., M.L. Knuth, K. Liber, B.R. Sheedy, R.L. Tunell and G.T. Ankley. 1999. Persistence and distribution of 4-nonylphenol following repeated application to littoral enclosures. Environ. Toxicol. Chem. 18:363-375. Hemmer, M.J., B.L. Hemmer, C.J. Bowman, K.J. Kroll, L.C. Folmer, D. Marcovich, M.D. Hoglund and N.D. Denstow. 2001. Effects of p-nonylphenol, methoxychlor and endosulfan on vitellogenin induction and expression in sheepshead minnow (Cyprindon variegatus). Environ. Toxicol. Chem. 20:336-343. Hewitt, L.M., L. Tremblay, G.J. Van Der Kraak, K.R. Solomon and M.R. Servos. 1998. Identification of the lampricide 3-trifluoromethyl-4-nitrophenol as an agonist for the rainbow trout estrogen receptor. Environ. Toxicol. Chem. 17:425-432. Holmes, S. B. and P. D. Kingsbury. 1980. The environmental impact of nonylphenol and the MataciT formulation. Part 1: Aquatic ecosystems. Report FPMX-35. Forest Pest Management Institute, Canadian Forestry Service, SaultSte. Marie, Ontario. Holcombe, G.W., G.L. Phipps, M.L. Knuth and T. Felhaber. 1984. The acute toxicity of selected substituted phenols, benzenes and benzoic acid esters to fathead minnows (Pimephales promelas). Environ. Pollut. (Series A) 35:367-381. Islinger, M., S. Pawlowski, H. HoUert, A. Volkl and T. Braumbeck. 1999. Measurement of vitellogenin-mRNA expression in primary cultures of rainbow trout hepatocytes in a non-radioactive dot blot/RNAse protection-assay. Sci. Total Environ. 233:109-122. 61 ------- Jobling, S. and J.P Sumpter. 1993. Detergent components in sewage effluent are weakly oestrogenic to fish: An in vitro study using rainbow trout ( Oncorhynchus mykiss) hepatocytes. Aquatic Toxicol. 27:361-372. Jobling, S., D. Sheahan, J.A. Osborne, P. Matthiessen and J.P. Sumpter. 1996. Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals. Environ. Toxicol. Chem. 15:194-202. Jones, S.B., L.B. King, L.C. Sappington, F.J. Dwyer, M. Ellersieck and D.R. Buckler. 1998. Effects of carbaryl, permethrin, 4-nonylphenol, and copper on muscarinic cholinergic receptors in brain of surrogate and listed fish species. Comp. Biochem. Physiol. 120:405-414. Kahl, M.D., E.A. Makynen, P.A. Kosian and G.T. Ankley. 1997. Toxicity of 4-nonylphenol in a life-cycle test with the midge Chironomus tentans. Ecotoxicol. Environ. Saf. 38:155-160. Keith, T.L., S.A. Snyder, C.G. Naylor, C.A. Staples, C. Summer, K. Kannan and J.P. Giesy. 2001. Identification and quantitation of nonylphenol ethoxylates and nonylphenol in fish tissues from Michigan. Environ. Sci. Technol. 35:10-13. Kelly, S.A. and R.T. Di Giulio. 2000. Developmental toxicity of estrogenic alkylphenols inkillifish (Fundulus heteroclitus). Environ. Toxicol. Chem. 19:2564-2570. Kinnberg, K., B. Korsgaard, P. Bjerregaard and A. Jespersen. 2000. Effects of nonylphenol and 17p-estradiol on vitellogenin synthesis and testis morphology in male platyfish Xiphorphorus maculatus. J. Exper. Biol. 203:171-181. Kitajima, F., C.G. Satuito, H. Hirota, I. Katsuyama and N. Fusetani. 1995. A new screening method for antifouling substances against the young mussels Mytilus edulis galloprovincialis. Fish. Sci. 61:578-583.. 62 ------- Kloas, W., I. Lutz and R. Einspanier. 1999. Amphibians as a model to study endocrine disrupters: II. Estrogenic activity of environmental chemicals in vitro and in vivo. Sci. Total Environ. 225:59- 68. Knudsen, F.R. and T.G. Pottinger. 1999. Interaction of endocrine disrupting chemicals, singly and in combination, with estrogen-, androgen-, and corticosteroid-binding sites in rainbow trout (Oncorhynchus mykiss). Aquat. Toxicol. 44:159-170. Kopf, W. 1997. Wirkung endodriner stoffe in biotests mit wasserorganismen. In: Stoffe mit endokriner wirkung in wasser. Bayerisches landesamt fur wasserwirt schaft, Institut fur Wasserforschung, Munchen. 12pp. Kusk, K.O. and L. Wollenberger. 1999. Fully defined saltwater medium for cultivation of and toxicity testing with marine copepod Acartia tonsa. Environ. Toxicol. Chem. 18:1564-1567. Kwak, H., M. Bae, M. Lee, Y. Lee, B. Lee, K. Kang, C. Chae, H. Sung, J. Shin, J. Kim, W. Mar, Y. Sheen and M. Cho. 2001. Effects of nonylphenol, bisphenol A, and their mixture on the viviparous swordtail fish (Xiphophorus helleri). Environ. Toxicol. Chem. 20:787-795. Lamche, G. and P. Burkhardt-Holm. 2000. Nonylphenol provokes a vesiculation of the golgi apparatus in three fish epidermis cultures. Ecotoxicol. Environ. Saf. 47:137-148. Larsson, D.G.J., M. Adolfsson-Erici, J. Parkkonen, M. Pettersson, A.H. Berg, P. Olsson and L. Forlin. 1999. Ethinyloestradiol - an undesired fish contraceptive? Aquat. Toxicol. 45:91-97. LeBlanc, G.A., S. Mu and C.V. Rider. 2000. Embryotoxicity of the alkylphenol degradation product 4-nonylphenol to the crustacean Daphnia magna. Environ. Health Perspect. 108:1133-1138. Lech, J. J., S. K. Lewis and L. Ren. 1996. In vivo estrogenic activity of nonylphenol in-rainbow trout. Fund. Appl. Toxicol. 30:229-232. 63 ------- Levine, C. and M.A. Cheney. 2000. Metabolic responses to acute toxicity of alkylphenols and alkylphenol polyethoxylates in Elliptic complanata measured by calorespirometry. Environ. Toxicol. Chem. 19:1906-1910. Lewis, M.A. 1991. Chronic and sublethal toxicities of surfactants to aquatic animals: A review and risk assessment. Wat. Res. 25:101-113. Lewis, S. K. and J. J. Lech. 1996. Uptake, disposition, and persistence of nonylphenol from water in rainbow trout (Oncorhynchus mykiss). Xenobiotica 26:813-819. Liber, K., J. A. Gangl, T. D. Corry, L. J. Heinis and F. S. Stay. 1999. Lethality and bioaccumulation of 4-nonylphenol in bluegill sunfish in littoral enclosures. Environ. Toxicol. Chem. 18:394-400. Loomis, A.K. and P. Thomas. 1999. Binding characteristics of estrogen receptor (ER) in Atlantic croaker (Micropogonias undulatus) testis: Different affinity for estrogens and xenobiotics from that of hepatic ER. Biol. Reprod. 61:51-60. Lussier, S.M., D, Champlin, J. LiVolsi, S. Poucher and RJ. Pruell. 2000. Acute toxicity of para- nonylphenol to saltwater animals. Environ. Toxicol. Chem. 19:617-621. Lutz, I. and W. Kloas. 1999. Amphibians as a model to study endocrine disrupters: I. Environmental pollution and estrogen receptor binding. Sci. Total Environ. 225:49-57. Lye, C.M., C.L.J. Frid, M.E. Gill, D.W. Cooper and D.M. Jones. 1999. Estrogenic alkylphenols in fish tissues, sediments, and waters from the U.K. Tyne and Tees estuaries. Environ. Sci. Technol. 33:1009-1014. MacPhee, C. and R. Ruelle. 1969. Lethal effects of 1888 chemicals upon four species offish from western North America. Bulletin No. 3, Forest, Wildlife and Range Experiment Station, University of Idaho, Moscow, ID. 112 p. 64 ------- •ll Madsen, S.S., A.B. Mathiesen and B. Korsgaard. 1997. Effects of 17 p-estradiol and 4-nonylphenol on smoltification and vitellogenesis in Atlantic salmon (Salmo salar). Fish Physiol. Biochem. 17:303- 312. Magliulo, L., M.P. Schreibman and J.L. Cepriano. 1998. Disruption of the brain-pituitary-gonad axis of platyfish due to hormone mimicking environmental pollutants. Am. Zool. 38:112A. Maguire, R.J. 1999. Review of the persistence of nonylphenol and nonylphenol ethoxylates in aquatic environments. Wat. Qual. Res. J. Can. 34:37-78. Maki, H., H. Okamura, I. Aoyama and M. Fujita. 1998. Halogenation and toxicity of the biodegradation products of a nonionic surfactant, nonylphenol ethoxylate. Environ. Toxicol. Chem. 17:650-654. Manzano, M.A., J.A. Perales, D. Sales and J.M. Quiroga. 1998. Effect of concentration on the biodegradation of a nonylphenol polyethoxylate in river water. Bull. Environ. Contam. Toxicol. 61:489-496. Manzano, M.A., J.A. Perales, D. Sales and J.M. Quiroga. 1999. The effect of temperature on the, biodegradation of a nonylphenol polyethoxylate in river water. Wat. Res. 33:2593-2600. Marcomini, A., B. Pavoni, A. Sfriso and A.A. Orio. 1990. Persistent metabolites of alkylphenol polyethoxylates in the marine environment. Mar. Chem. 29:307-324. McLeese, D.W., D.B. Sargeant, C.D. Metcalfe, V Zitko and L.E. Burridge. 1980a. Uptake and excretion of aminocarb, nonylphenol, and pesticides diluent 585 by mussels (Mytilus edulis}. Bull. Environ. Contam. Toxicol. 24:575-581. McLeese, D.W., V. Zitko, C.D. Metcalf and D.B. Sergeant. 1980b. Lethality of aminocarb and the components of the aminocarb formulation to juvenile Atlantic salmon, marine invertebrates and a freshwater clam. Chemosphere. 9:79-82. 65 ------- McLeese, D.W., V. Zitko, D.B. Sargeant, L. Burridge and C.D. Metcalfe. 1981. Lethality and accumulation of alkylphenols in aquatic fauna. Chemosphere 10:723-730. Meldahl, A. C., K. Nithipatikom and J. J. Lech. 1996. Metabolism of several 14C-nonylphenol isomers by rainbow trout (Oncorhynchus mykiss): in vivo and in vitro microsomal metabolites. Xenobiotica 26:1167-1180. Miles-Richardson, S.R., S.L. Pierens, K.M. Nichols, VJ. Kramer, E.M. Snyder, S.A. Snyder, J.A. Render, S.D. Fitzgerald and J.P. Giesy. 1999. Effects of waterborne exposure to 4-nonylphenol and nonylphenol ethoxylate on secondary sex characteristics and gonads of fathead minnows (Pimephales promelas). Environ. Res. (Series A) 80:S122-S137. Milligan, S.R., 0. Khan and M. Nash. 1998. Competitive binding of xenobiotic estrogens to rat alpha-fetoprotein and to sex steroid binding proteins in human and rainbow trout ( Oncorhynchus mykiss) plasma. Gen. Comp. Endocrinol. 112:89-95. Moore, S.B., R.A. Diehl, J.M. Earnhardt and G.B. Avery. 1987. Aquatic toxicities of textile surfactants. Text. Chem. Color. 19:29-32. Muller, R. 1980. Fish toxicity and surface tension of non-ionic surfactants: investigations of antifoam agents. J. Fish. Biol. 16:585-589. Naylor, C.G. 1992. Environmental fate of alkyIphenol ethoxylates. Soap Cosmetics Chemical Specialities. August. Naylor, C.G., J.P. Mieure, W.J. Adams, J.A. Weeks, F.J. Castaldi, L.D. Ogle and R.R. Romano. 1992. Alkylphenol ethoxylates in the environment. J. Am. Oil Chem. Soc. 69:695-708. Nimrod, A.C. and W.H. Benson. 1996. Estrogenic responses to xenobiotics in channel catfish (Ictaluruspunctatus). Mar. Environ. Res. 42:155-160. 66 ------- Nimiod, A.C. and W.H. Benson. 1997. Xenobiotic interaction with and alteration of channel catfish estrogen receptor. Toxicol. Appl. Pharmacol. 147:381-390. Nimrod, A.C. and W.H. Benson. 1998. Reproduction and development of Japanese medaka following an early life stage exposure to xenoestrogens. Aquat. Toxicol. 44: 141-156. O'Halloran, S. L., K. Liber, J. A. Gangl and M. L. Knuth. 1999. Effects of repeated exposure to 4- nonylphenol on the zooplankton community in littoral enclosures. Environ. Toxicol. Chem. 18:376- 385. Palmer, B.D., S.K. Palmer, C. Burch, J. Danyo and K.W. Selcer. 1998. Effects of endocrine disrupting chemicals on amphibians. Am. Zool. 38(5): Abstract No. 177A. Patoczka, J. and G.W. Pulliam. 1990. Biodegradation and secondary effluent toxicity of ethoxylated surfactants. Wat. Res. 24:965-972. Pedersen, S.N., L.B. Christiansen, K.L. Pedersen, B. Korsgaard and P. Bjerregaard. 1999. In vivo estrogenic activity of branched and linear alkylphenols in rainbow trout (Oncorhynchus mykiss). Sci. Tot. Environ. 233:39-96. Petit, F., P. Le Goff, J.P. Cravedi, Y. Valotaire and F. Pakdel. 1997. Two complementary bioassays for screening the estrogenic potency of xenobiotics: recombinant yeast for trout estrogen receptor and trout hepatocyte cultures. J. Mol. Endocrinol. 19:321-335. Petit, F., P. Le Goff, J.P. Cravedi, 0. Kah, Y. Valotaire and F. Pakdel. 1999. Trout estrogen receptor sensitivity to xenobiotics as tested by different bioassays. Aquaculture. 177:353-365. Prasad, R. 1986. Effects of nonylphenol adjuvant on macrophytes. In: Adjuvants and Agrochemicals,--Ch0w, P.N.P. (Ed.). Vol. 1, Mode of action and physiological activity First International Symposium. Brandon, Manitoba, Canada. August 5-7. XIV+ 207 pp. 67 ------- Preston, B.L., T.W Snell, T.L. Robertson and BJ. Dingmann. 2000. Use of freshwater rotifer Brachionus calyciflorus in screening assay for potential endocrine disrupters. Environ. Toxicol. Chem. 19:2923-2928. Purdom, C.E., P.A. Hardiman, V.J. Bye, N.C. Eno, C.R. Tyler and J.P. Sumpter. 1994. Estrogenic effects of effluents from sewage treatment works. Chem. and Ecol. 8:275-285. Radian Corp. 1990. Nonylphenol and nonylphenol ethoxylates in river water and bottom sediments- January 1989-August 1990. Final Report to Alkylphenol and Ethoxylates Panel, Chemical Manufacturers Association. Reed, H.W.B. 1978. ALkylphenols. In: Kirk-Othmer: Encyclopedia of chemical technology. Grayson M. and EcKroth D. (Eds.). 3rd ed., Vol. 2, John Wiley and Sons, New York. pp. 72-96. Ren, L., D. Lattier and J. J. Lech. 1996a. Estrogenic activity in rainbow trout determined with a new cDNA probe for vitellogenesis, pSGSVgl.l. Bull. Environ. Contam. Toxicol. 56:287-294. Ren, L., S.K. Lewis and J.J. Lech. 1996b. Effects of estrogen and nonylphenol on the post- transcriptional regulation of vitellogenin gene expression. Chemico-Biol. Interact. 100:67-76. Rice, C.D., L.E. Roszell, M.M. Banes and R.E. Arnold. 1998. Effects of dietary PCBs and nonyl- phenol on immune function and CYP1A activity in channel catfish, Ictalurus punctatus. Mar. Environ. Res. 46:351-354. Rouuedge, E.J. and J.P. Sumpter. 1996. Estrogenic activity of surfactants and some of then- degradation products assessed using a recombinant yeast screen. Environ. Toxicol. Chem. 15:241- 248. Roufledge, E.J. and J.P. Sumpter. 1997. Structural features of alkylphenolic chemicals associated with estrogenic activity. Jour. Biol. Chem. 272:3280-3288. 68 ------- Roy F. Western Inc. 1990. Determination of the vapor pressure of 4-nonylphenol. Final Report Study No. 90-047. Roy F. Weston Inc., Environmental Fate and Effects Laboratory, 254 Welsh Pool Road, Lionville, PA. 15 August 1990. Schmude, K. L., K. Liber, T. D. Corry and F S. Stay. 1999. Effects of 4-nonylphenol onbenthic macromvertebrates and insect emergence in littoral enclosures. Environ. Toxicol. Chem. 18:386-393. Schultz, T.W. 1997. Tetratox: Tetrahymena pyriformis population growth impairment endpoint A surrogate for fish lethality. Toxicol. Methods. 7:289-309. Schwaiger, J., O.K. Spieser, C. Bauer, H. Ferling, U. Mallow, W. Kalbfus and R.D. Negele. 2000. Chronic toxicity of nonylphenol and ethinylestradiol: haematological and histopathological effects in juvenile common carp (Cyprinus carpio). Aquat. Toxicol. 51:69-78. Schwaiger, J., U. Mallow, H. Ferling, S. Knoerr, T. Braunbeck, W. Kalbfus and R.D. Negele. 2002. How estrogenic is nonylphenol: A trans generational study using rainbow trout ( Oncorhynchus mykiss) as a test organism. Aquat. Toxicol. 59:177-189. Servos, M.R. 1999. Review of the aquatic toxicity, estrogenic responses and bioaccumulation of , alkylphenols and alkylphenol polyethoxylates. Wat. Qual. Res. J. Can. 34:123-177. Shackelford, W.M., D.M. Cline, L. Faas and G. Kurth. 1983. Evaluation of automated spectrum matching for survey identification of wastewater components by gas chromatography-mass spectrometry. PB83-182931. National Technical Information Service, Springfield, VA. Shang, D.Y., R.W. MacDonald and M.G. Ikonomou. 1999. Persistence of nonylphenol ethoxylate surfactants and their primary degradation products in sediments from near a municipal outfall hi the Strait of Georgia, British Columbia, Canada. Environ. Sci. Technol. 33:1366-1372. 69 ------- i Shurin, J.B. and S.I. Dodson. 1997. Sublethal toxic effects of cyanobacteria and nonylphenol on environmental sex determination and development in Daphnia. Environ. Toxicol. Chem. 16:1269-1276. Sonnenschein, C. and A.M. Soto. 1998. An updated review of environmental estrogen and androgen mimics and antagonists. J. Steroid Biochem. Molec. Biol. 65:143-150. Soto, A.M., H. Justicia, J.W. Wray and C. Sonnenschein. 1991. £>-nonylphenol: An estrogenic xenobiotic released from modified polystyrene. Environ. Health Perspect. 92:167-173. Soto, A.M., T.M. Lin, H. Justicia, R.M. Silvia and C. Sonnenschein. 1992. An "in culture" bioassay to assess the estrogenicity of xenobiotics (E-SCREEN). In: Advances in Modern Environmental Toxicology. Volume XXI. Chemically-induced alterations in sexual and functional development: The wildlife/human connection. T. Colburn and C. Clement (Eds.). Princeton Scientific Publishing Co., Inc., NJ. 403 pp. Spieser, O.K., J. Schwaiger, H. Ferling, W. Kalbfus and R. Negele. 1998. Effects of nonylphenol and ethinyl-estradiol on swimming behavior of juvenile carp. Abstract for Annual Meeting. International Association for Great Lakes Research. Hamilton, Ontario, Canada, pp. 37-38. Staples, C.A., J. Weeks, I.E. Hall and C.G. Naylor. 1998. Evaluation of aquatic toxicity and bioaccumulation of C8- C9-alkylphenol ethoxylates. Environ. Toxicol. Chem. 17:2470-2480. Staples, C.A., J.B. Williams, R.L. Blessing and P.T. Varineau. 1999. Measuring the biodegradability of nonylphenol, ether carboxylates, octylphenol, ether carboxylates, and nonylphenol. Chemosphere 38:2029-2039. Stephan, C.E., D.I. Mount, D.J. Hansen, J.H. Gentile, G.A. Chapman and W.A. Brungs. 1985. Guidelines for deriving numerical national water quality criteria for the protection of aquatic organisms and their uses. PB85-227049. National Technical Information Service, Springfield, VA. 70 ------- TT Sumpter, J.P 1998. Xenoendocrine disrupters — environmental impacts. Toxicol. Lett. 102-103: 337-342. Sundaram, K.M.S. and S. Szeto. 1981. The dissipation of nonylphenol in stream and pond water under simulated field conditions. J. Environ. Sci. Health (Part B) B16(6):767-776. Sundaram, K.M.S., S. Szeto, R. Kindle and D. MacTavish. 1980. Residues of nonylphenol in spruce foliage, forest soil, stream water and sediment after its aerial application. J. Environ. Sci. Health (Part B)B15(4):403-419. Tabira, Y., M. Nakai, D. Asai, Y. Yakabe, Y. Tahara, T. Shinmyozu, M. Noguchi, M. Takatsuki and Y. Shimohigashi. 1999. Structural requirements of para-alkyIphenols to bind to estrogen receptor. Eur. J. Biochem. 262:240-245. Tagliabue, M.D. 1993. Nonylphenol Champia results. Memo dated February 23 to S. Poucher, Science Applications International Corporation, Narragansett, RI. 6 pp. Takasawa, R., H. Etoh, A. Yagi, K. Sakata and K. Ina. 1990. Nonylphenols as promising antifouling agents found by a simple bioassay method using the blue mussel, Mytilus edulis. Agric. Biol. Chem. 54:1607-1610. Tanghe, T., G. Devriese and W. Verstraete. 1999. Nonylphenol and estrogenic activity in aquatic environmental samples. J. Environ. Qual. 28:702-709. Thibaut, R., L. Debrauwer, D. Rao and J. Cravedi. 1998. Characterization of biliary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss). Xenobiotica. 28:745-757. Thibaut, R., L. Debrauwer, D. Rao and J.P Cravedi. 1999. Urinary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss). Sci. Total Environ. 233:193-200. 71 ------- TT Tsuda, T., A. Takino, M. Kojima, H. Harada, K. Muraki and M. Tsuji. 2000. 4-Nonylphenols and 4-tert-octylphenol in water and fish from rivers flowing into Lake Biwa. Chemosphere 41:757-762. Tremblay, L. and G. Van Der Kraak. 1998. Use of a series of homologous in vitro and in vivo assays to evaluate the endocrine modulating actions of p-sitosterol in rainbow trout. Aquat. Toxicol. 43:149-162. Turner, A.H:, F.S. Abram, V.M. Brown and H.A. Painter. 1985. The biodegradability of two primary alcohol ethoxylate nonionic surfactants under practical conditions, and the toxicity of biodegradation products to rainbow trout. Wat. Res. 19:45-51. University of Wisconsin-Superior. 1985. Acute toxicities of organic chemicals to fathead minnows (Pimephales promelas). Volume II. D.L. Geiger, C.E. Northcott, DJ. Call and L.T. Brooke (Eds.). Center for Lake Superior Environmental Studies, University of Wisconsin-Superior, Superior, WI. 326pp. U.S. EPA. 1983. Water quality standards regulation. Federal Regist. 48:51400-51413. Novembers. U.S. EPA. 1985. Appendix B - Response to public comments on "Guidelines for deriving numerical national water quality criteria for the protection of aquatic organisms and their uses." Federal Regist. 50:30793-30796. July 29. U.S. EPA. 1986. Chapter 1-Stream design flow for steady-state modeling. In: Book VI-Design conditions. In: Technical guidance manual for performing waste load allocation. Office of Water, Washington, DC. August. U.S. EPA. 1987. Permit wriiers guide co water quality-based permitting for toxic pollutants. EPA- 440/4-87-005. Office of Water, Washington, DC. 72 ------- U.S. EPA. 1991. Technical support document for water quality-based toxics control. EPA-505/2-90- 001 Office of Water, Washington, DC, March; or PB91-127415, National Technical Information Service, Springfield, VA. U.S. EPA. 1994. Water Quality Standards Handbook: 2nd ed. EPA-823-B-94-005a,b. Washington, DC. USITC. 1981. Synthetic organic chemicals: United States production and sales, 1980. United States International Trade Commission Publication No. 1183. U.S. Govt. Printing Office, Washington, DC 20402. 327 p. USITC. 1989. Synthetic organic chemicals: United States production and sales, 1988. United States International Trade Commission Publication No. 2219. U.S. Govt. Printing Office, Washington, DC 20402. Varma, M.M. and D. Patel. 1988. Nonionic surfactants inperspecitive. J. Environ. Systems 18:87-96. Veith, G.D. and O.G. Mekenyan. 1993. A QSAR approach for estimating the aquatic toxicity of soft electrophiles (QSAR for soft electrophiles). Quant. Struct. Act. Relat. 12:349-356. ViUenueve, D.L., S.A. Villalobos, T.L. Keith, E.M. Snyder, S.D. Fitzgerald and J.P. Giesy. 2002. Effects of waterborne exposure to 4-nonylphenol on plasma sex steroid and vitellogenin concentrations in sexually mature male carp (Cyprinus carpio). Chemosphere 47:15-28. Ward, T.J. and R.L. Boeri. 1990a. Acute static toxicity of nonylphenol to the freshwater alga Selenastrum capricomutum. EnviroSystems Study No. 8969-CMA. Resource Analysts, Inc., Hampton, NH. 41 pp. Ward, T.J. and R.L. Boeri. 1990b. Acute flow through toxicity of nonylphenol to the mysid, Mysidopsis bahia. Study Number 8974-CMA. EnviroSystems, Hampton, NH. 35 pp. 73 ------- Ward, TJ. and R.L. Boeri. 1990c. Acute flow through toxicity of nonylphenol to the sheepshead minnow, Cyprinodon variegatus. Study Number 8972-CMA. EnviroSystems, Hampton, NH. 34 pp. Ward, TJ. and R.L. Boeri. 1990d. Acute static toxicity of nonylphenol to the marine alga Skeletonema costatum. Study Number 8970-CMA. EnviroSystems, Hampton, NH. 42 pp. Ward, TJ. and R.L. Boeri. 1991a. Bioconcentration test with nonylphenol and the fathead minnow, Pimephales promelas. Study Number 8975-CMA. Envirosystems, Hampton, NH. 72pp. Ward, TJ. and R.L. Boeri. 1991b. Chronic toxicity of nonylphenol to the mysid, Mysidopsis bahia. Study Number 8977-CMA. EnviroSystems, Hampton, NH. 61 pp. Ward, T J. and R.L. Boeri. 1991c. Early life stage toxicity of nonylphenol to the fathead minnow, Pimephales promelas. Study Number 8979-CMA. EnviroSystems, Hampton, NH. 59 pp. Ward, TJ. and R.L. Boeri. 1992. Toxicity of nonylphenol to the tadpole Rana catesbiana. Study Number 8981-CMA. EnviroSystems, Hampton, NH. 78 pp. Weinberger, P and R. Greenhalgh. 1984. Some adjuvant effects on die fate of fenitrothion and aminocarb. Environm. Toxicol. Chem. 3:325-334. Weinberger, P. and S. lyengar. 1983. Effects of aminocarb, fuel oil 585 and nonylphenol on the growth and development ofLemna minor L. Dev. Ecol. Environ. Qual. Shuval, H. I. (Ed.). Proc. Int. Meet. Isr. Ecol. Soc. PP 595-607. Weinberger, P. and M. Rea. 1981. Nonylphenol: A perturbant additive. Canadian Tech. Rep. Fish Aquat. Sci. 990:370-381. Weinberger, P., C. DeChacin and M. Czuba. 1987. Effects of nonyl phenol, a pesticide surfactant, on some metabolic processes of Chlamydomonas segnis. Can. J. Bot. 65:696-702. 74 ------- White, R., S. Jobling, S.A. Hoare, J.P. Sumpter and M.G. Parker. 1994. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175-182. Wood, E. M. ' 1953. The toxicity of 3400 chemicals to fish. Report of Fish and Wildlife Service, Kearneysville, West Virginia. EPA 560/6-87-002 Office of Toxic Substances, Washington, DC, August; or PB87-200-275 National Technical Information Service, Springfield, VA. Yadetie, F., A. Arukwe, A. Goksoyr and R. Male. 1999. Induction of hepatic estrogen receptor in juvenile Atlantic salmon in vivo by the environmental estrogen, 4-nonylphenol. Sci. Total Environ. 233:201-210. Yoshioka, Y. 1985. Testing for the toxicity of chemicals with Tetrahymena pyriformis. Sci. Total Environ. 43:149-157. 75 ------- |