OCR error (C:\Conversion\JobRoot\00000CEP\tiff\20013NI9.tif): Unspecified error

-------

-------
                                    NOTICES
This document has been reviewed by the Criteria and Standards Division, Office
of Water Regulations and Standards, U.S.  Environmental Protection Agency,  and
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.
                                       11

-------
                                   FOREWORD
      Section 304(a)(l) of the Clean Water Act 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.  Pursuant to that end, this
document proposes water quality criteria for the protection of aquatic life.
These criteria do not involve consideration of effects on human health.

      This document is a draft, distributed for public review and comment.
After considering all public comments and making any needed changes, EPA will
issue the criteria in final form, at which time they will 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).  In section 304, the term
represents a non-regulatory, scientific assessment of 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, then they become maximum acceptable
pollutant concentrations that can be used to derive enforceable permit limits
for discharges to such waters.

      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 before
incorporation into water quality standards.  Guidance is available from EPA to
assist States in the modification of section 304(a)(l) criteria, and in the
development of water quality standards.  It is not until their adoption as
part of State water quality standards that the criteria become regulatory.
                                    Martha G. Prothro
                                    Director
                                    Office of Water Regulations and Standards
                                     111

-------
                                ACKNOWLEDGMENTS
Daniel J. Call
(freshwater author)
University of Wisconsin-Superior
Superior, Wisconsin
Jeffrey L.  Hyland
Richard K.  Peddicord
(saltwater authors)
Battelle Ocean Sciences
Duxbury, Massachusetts
Charles E. Stephan
(document coordinator)
Environmental Research Laboratory
Duluth, Minnesota
David .!.  Hansen
(saltwater coordinator)
Environmental Research Laboratory
Narragansett, Rhode Island
                                       IV

-------
                                   CONTENTS








                                                                         Page




Notices	   i i



Foreword	  i i i



Acknowledgments	   iv




Tables	   vi








Introduction	    1



Acute Toxicity to Aquatic Animals	    2



Chronic Toxictty to Aquatic Animals	    4




Toxicity to Aquatic Plants	    6



Bioaccumulation	    6



Other Data	    7



Unused Data	    8



Summary	    8



National Criteria	    9




Implementation	   10








References	   25

-------
                                    TABLES
                                                                         Page



1.   Acute Toxicity of 2,4,5-Trichlorophenol  to Aquatic Animals 	   12



2.   Chronic Toxicity of 2,4,5-Trichlorophenol  to Aquatic Animals 	   16



3.   Ranked Genus Mean Acute Values with Species Mean Acute-Chronic




      Ratios 	   18



4.   Toxicity of 2,4,5-Trichlorophenol to Aquatic Plants	   21




5.   Bioaccumulation of 2,4,5-Trichlorophenol by Aquatic Organisms 	   22




6.   Other Data on Effects of 2,4,5-Trichlorophenol on Aquatic Organisms .   23
                                       VI

-------
Introduction



    2,4,5-Trichlorophenol  (2,4,5-TCP)  is  a  crystalline  solid  at  room



temperature.   It is soluble in water up to  2,000  mg/L,  has  an ionization



constant (pKa) of 7.0 to 7.4 (Ahlborg  and Thunberg  1980;  Doedens  1964; U.S.



EPA 1980),  and a log n-octanol/water partition coefficient  of 3.70  (Hansch



and Leo 1979).  2,4,5-TCP is used as an algicide,  fungicide,  and  bactericide



and as an antimildew and preservation agent in cooling  towers,  pulp mills,



and in hide and leather processing (Ahlborg and Thunberg  1980;  U.S. EPA



1980).  It  is also used in the production of the  pesticides erbon,



fenchlorphos, fenoprop (2,4,5-TP), hexachlorophene,  and 2,4,5-trichloro-



phenoxyacetic acid (2,4,5-T) (Ahlborg and Thunberg  1980;  Buikema et al.  1979;



Doedens 1964; Kozak et al.  1979;  Stolzenburg and Sullivan 1984).




    Contamination of waters with 2,4,5-TCP  and other chlorophenols  has



resulted from the use of chlorophenoxyacetic acid herbicides containing




chlorophenolic impurities,  from the chlorination of waste treatment plant




effluents,  and from pulp bleaching (Ahlborg and Thunberg 1980; Buikema et al.



1979;  Jolley et al. 1976;  Rockwell and Larsen 1978).  Residues have been




detected in  fish and other organisms collected downstream from pulp mills




(Paasivirta  et al. 1985).   Considerable concern has been expressed  that



2,3,7,8-tetrachlorodibenz'o-p-dioxin (TCDD)  can be an impurity in 2,4,5-TCP



(Anonymous  1976; Firestone et al. 1972).



    At very  low concentrations, some phenolic compounds impair the  odor  and/




or taste of water and fish.  2,4,5-TCP has  a taste  threshold concentra-



tion in water of 1 pg/L and an odor threshold concentration of 200  pg/L




(Dietz and  Traud 1978).  However, Shumway and Palensky (1973) did not observe




flavor impairment in rainbow trout exposed  to 320 pg/L for 48 hr.




    An understanding of the "Guidelines for Deriving Numerical National  Water




Quality Criteria for the Protection of Aquatic Organisms and Their  Uses"



                                       1

-------
(Stephan et al.  1985),  hereinafter referred to  as  the  Guidelines,  and  the



response to public comment (U.S.  EPA 1985a) is  necessary  in order  to



understand the following text,  tables,  and calculations.   Results  of  such



intermediate calculations as recalculated LCSOs and Species Mean Acute Values



are given to four significant figures to prevent round off error in



subsequent calculations, not to reflect the precision  of  the value.   The



criteria presented herein supersede the aquatic life information in a



previous criteria document (U.S.  EPA 1980) because these  criteria  are based




on additional information.  The latest literature  search  for information  for



this document was conducted in July, 1986; some more recent information was



included.  Data that are  in the files of the U.S.  EPA's Office of  Pesticide




Programs concerning the effects of 2,4,5-TCP on aquatic life and its uses



have not been evaluated for possible use in the derivation of aquatic life




criteria.








Acute Toxicity to Aquatic Animals




    Data that can be used, according to the Guidelines, in the derivation of



Final Acute Values for 2,4,5-TCP are presented in Table 1.  The rainbow



trout, Salmo gairdneri. was the most sensitive freshwater  species with a



96-hr LC50 of 260 Mg/L.   The cladoceran, Daphnia magna. was the most



resistant species, with a 48 hr EC50 of 2,660 pg/L.  The  range of acute



values for fish was from  260 ng/L  in the trout to 3,060 MgA  in the



guppy, Poecilia reticulata.  A similar range for  invertebrates extended from




336 Mg/L in.the amphipod, Gammarus  pseudolimnaeus to 2,660 jug/L in




Daphnia.



    The effect of pH on the acute  toxicity of  2,4,5-TCP was examined  with  the




guppy, Poecilia reticulata  (Saarikoski and Viluksela  1981,1982; Salkinoja-




Salonen et al. 1981).  The  96-hr LCSOs at  pH = 6, 7,  and  8 were 990,  1,240,




                                       2

-------
and 3,060 MgA.  respectively.   The freshwater criterion was  not made




pH-dependent because data are available for only one  species.




    Freshwater Species Mean Acute Values (Table 1)  were determined from the



available acute  values.   Genus Mean Acute Values (Table 3)  were the  same as




the Species Mean Acute Values.  Of the ten freshwater genera for which mean



acute values are available, the most sensitive genus,  Sal mo.  is about  10



times more sensitive than the most resistant, Daphnia.   The  freshwater Final



Acute Value for 2,4,5-TCP was calculated to be 199.2  ng/L using the



procedure described in the Guidelines and the Genus Mean Acute Values  in



Table 3.  The Final Acute Value is lower than the lowest available Species




Mean Acute Value.



    The stock of 2,4,5-TCP that was used in freshwater acute tests reported




by Sabourin et al. (1986) and Spehar (1986) was found to contain U.2  ng/g of



the contaminant, 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (Durhan 1986).




This resulted in estimated 2,3,7,8-TCDD concentrations in the exposure water




as high as 115 pg/L (Table 1).  It is not known if 2,3,7,8-TCDD



concentrations of 115 pg/L or less had an effect upon the observed toxicity.




Concentrations of 2,3,7,8-TCDD were not determined in the other freshwater



acute tests.



    Tests of the acute toxicity of 2,4,5-TCP to resident North American



saltwater animals have been performed with six species of invertebrates and



five species of fish (Table 1).  The range of acute values for  invertebrates




extends from 492 Mg/L for the amphipod, Rhepoxvnius abronius (Battelle



Ocean Sciences 1987) to 3,830 ng/L for adult mysids,  Mvsidopsi s bahia




(U.S. EPA 1978).  The range of acute values for saltwater fish  is narrower,



from 566 jug/L for both juvenile English sole, Parophys vetulus. and adult




Pacific sand lance, Ammodvtes hexapterus (Battelle Ocean Sciences 1987) to

-------
1,660 ng/L for both juvenile sheepshead minnows,  Cvprinodon variegatua



(Heitrauller et al.  1981)  and juvenile inland silversides,  Menidia  beryl 1ina



(Hughes and Pruell  1987).




    The 24- and 96-hr LCSOs differed little with  both mysids and sheepshead




minnows (Heitmuller et al.  1981;  U.S. EPA 1978).   In contrast,  mortalities



continued throughout acute  tests  with polychaete  worms,  archiannelids,  and



inland silversides  (Battelle Ocean Sciences 1987).   Rao  et al.  (1981)  found



that 2,4,5-TCP was  about twice as toxic to molting  grass shrimp as it  was  to




intermolt shrimp.   The effect of  environmental  factors such as  salinity and



temperature on the  acute toxicity of 2,4,5-TCP to saltwater animals is not



known.




    Of the ten genera for which saltwater Genus Mean Acute Values are




available (Table 3), the most sensitive genus,  Rhepoxynius. is  about 7.8



times more sensitive than the most resistant, Mysidoosis.   The  six most




sensitive genera are within a factor of 1.8 and include  four invertebrates




and two fishes.  The saltwater Final Acute Value  for 2,4,5-TCP was calculated



to be 472.9 Mg/L,  which is  lower  than the mean acute value for the most



sensitive tested saltwater species.








Chronic Toxicitv to Aquatic Animals



    The available data that are useable according to the Guidelines con-



cerning the chronic toxicity of 2,4,5-TCP are presented in Table 2.  In a




seven-day life-cycle test with Ceriodaphnia dubia.  all organisms died at a




concentration of 1,480 ^g/L (Spehar  1986).  A concentration of 746 ng/L




did not cause mortality, but significantly reduced production of young.  A




concentration of 375 pg/L affected neither survival nor reproduction.   The



resulting chronic value was 528.9 ng/L and the acute-chronic ratio was




3.294 (Table 2).



                                       4

-------
    In a 90-day early life-stage test with rainbow trout (Spehar 1986),  a



concentration of 441 /ig/L caused 100% mortality of swim-up larvae.   A



concentration of 208 ng/L did not affect hatchability or swim-up larvae,



but significantly (P <, 0.05) decreased survival of juveniles.   No adverse



effects were observed at 108 Mg/L or below.   The chronic value and



acute-chronic ratio were 149.9 MgA and 1-734,  respectively (Table 2).



    Fathead minnows, Pimephal es promelaj..  exposed to 160 pg/L were not



adversely affected  in an early life-stage test (Spehar 1986).   Reduced  growth



and approximately 50% mortality occurred at 342 p.g/L.  Complete mortality




was observed at 673 and 1,322 Mg/L.  The chronic value was 233.9 ng/L



and the acute-chronic ratio was 5.421 (Table 2).




    The stock 2,4,5-TCP that was used in the freshwater chronic tests




reported by Spehar  (1986) contained up to 14.2 ng/g of 2,3,7,8-TCDD (Durhan



1986).  This resulted in estimated maximum 2,3,7,8-TCDD concentrations  in the




exposure water of 40.9 pg/L in the Ceri odaphnia test, 6.3 pg/L in the rainbow




trout test, and 18.8 pg/L in the fathead minnow test.  It is not known at



present if 2,3,7,8-TCDD at these concentrations had any effect upon the




observed toxicity.



    The chronic toxicity of 2,4,5-TCP has been measured in salt water with



the inland silverside, Menidi a beryl 1ina (Hughes and Pruell 1987).  In this



early life-stage test, 86% of the embryos exposed to 104 MgA died before



hatching.   Survival of both embryos and fry was reduced at 59.6 Mg/L, but



no effects were detected at 25.1 ng/L.   The resulting chronic value was



38.68 Mg/L. and the acute-chronic ratio was 42.92 (Table 2).



    The available Species Mean Acute-Chronic Ratios are 3.294, 5.421, and




1.734 in fresh water and 42.92 in salt water (Table 3).  The freshwater  Final




Acute-Chronic Ratio of 3.140 was calculated as the geometric mean of the

-------
three ratios,  whereas 42.92 was used as the saltwater Final  Acute-Chronic



Ratio.   Division of the freshwater and saltwater Final  Acute Values  by  the



respective Final Acute-Chronic Ratios results in freshwater  and saltwater



Final Chronic  Values of 63.44 and 11.02 ng/L, respectively.   These  Final



Chronic Values are lower than the lowest available respective chronic  values



in fresh and salt water.








Toxicitv to Aquatic Plants




    Two toxicity tests with exposure periods of four or more days have  been



conducted on 2,4,5-TCP with aquatic plants (Table 4).  An EC50, based on



reduction of chlorophyll a., was 1,200 ng/L for the freshwater green alga,



Selenastrum capricornutum (U.S. EPA 1978).  The EC50, based on reduction in



chlorophyll a., was 890 pg/L for the saltwater diatom, Skeletonema



costatum. whereas the EC50 based on cell counts was 960 ng/L (U.S.  EPA



1978).   These  concentrations are above the Final Acute Values  for 2,4,5-TCP.




A Final Plant  Value, as defined in the Guidelines, cannot be obtained because




no test in which the concentrations of 2,4,5-TCP were measured and the



endpoint was biologically  important has been conducted with an important



aquatic plant  species.








Bioaccumulation



     In a bioconcentration test with the fathead minnow, equilibrium of




^C-labeled 2,4,5-TCP between water and fish occurred within 24  to 48 hr at




exposure concentrations of 4.8 and 49.3 ng/l (Call et al. 1980).  At the




higher concentration, 78.6% of the radiolabel was associated with 2,4,5-TCP




at the end of the 28-day uptake phase.  The  BCF was  1,410 and  the half-life




was  12 hr (Table 5).

-------
    Inland siIversides, Menidia beryl!ina.  that survived a 28-day early life-




stage toxicity test accumulated 2,4,5-TCP to concentrations between 47.2 and



71.3 times the concentration measured in test solutions (Table 5).   Biocon-



centration factors for grass shrimp,  Palaemonetes pugio.  exposed for one hour



to 14C-trichlorophenol were 13 for intermolt and 32 for new molt stages




(Table 6).  Concentrations after 12 hours of exposure of intermolts were



highest in the digestive tract and hepatopancreas and lowest in the cephalo-



thorax and abdomen.  Shrimp depurated 96% of accumulated 2,4,5-TCP in 24 hr




(Rao et al. 1981).



    No U.S. FDA action level or other maximum acceptable concentration in




tissue, as defined in the Guidelines, is available for 2,4,5-TCP.  Therefore,



a Final Residue Value cannot be calculated.








Other Data



    Additional data on the lethal and sublethal effects of 2,4,5-TCP on



aquatic species are presented in Table  6.  Exposures of an alga, Chlorella



pyrenoidosa.  to 2,4,5-TCP for 3 days at concentrations from 1,000 to



10,000 ng/L reduced chlorophyll by 12 to 100% (Huang and Gloyna 1967,



1968).  The 24-hr EC50 for the protozoan, Tetrahymena pyriformis. was



680 jug/L (Yoshioka et al.  1985).  A 24-hr exposure to 1,912 jug/L caused



100% mortality of lymnaeid snails (Batte and Swanson 1952).  A 24-hr EC50 of




2,080 M8/L **s obtained with the cladoceran, Daphnia magna (Devillers and



Chambon 1986).  A 48-hr exposure of rainbow trout to 2,4,5-TCP at




1,000 /ig/L resulted in 100% mortality (Shumway and Palensky 1973).  LCSOs




of 900. 533,  and 1,700 ng/L were obtained at 24 hr with the brown trout,




guppy, and goldfish,  respectively.

-------
    Ribo and Kaiser (1983)  reported a 30-min EC50 of 1,300 jug/L,  based  on

reduction in light production by the photoluminescent bacterium,

Photobacterium phosphoreum (Table 6).   Rao et al.  (1981)  found that  exposure

to 500 and 750 Mg/L for 9 days inhibited limb regeneration by  the grass

shrimp,  Palaemonetes pugio.   Limb regeneration was not affected in

100 jug/L.



Unused Data

    Some data on the effects of 2,4,5-TCP on aquatic organisms were  not used

because  the tests were conducted with species that are not resident  in North

America  (e.g., Hattori et al. 1984; Hosaka et al. 1984; Nagabhushanam and

Vaidya 1981).  Kaiser et al. (1984), LeBlanc (1984). and Persson (1984)

compiled data from other sources.  Bringmann and Kuhn (1982) cultured

organisms in one water and conducted tests in another.  Dojlido  (1979) did
                                                            '•>
not specify which trichlorophenol was used.  Blackman et al. (l955a,b)

conducted tests at pH below 6.5.

    Results were not used when the test procedures were not adequately

described (Knie et al. 1983).  Studies by Kobayashi et al.  (1984) on the

sulfate conjugating enzyme  system and McKim et al.  (1985) on the efficiency

of chemical uptake by fish  gills did not provide data pertinent  to water

quality criteria.



Summary

    The acute toxicity of 2,4,5-trichlorophenoi to  freshwater  animals  ranged

from 260 ng/L for the rainbow trout to 2,660 ^g/L for Daphnia  magna.

The acute toxicity of 2,4,5-TCP  to the guppy  increased as the  pH of the  water

decreased.  Chronic toxicity values for three freshwater  species ranged  from

-------
150 to 529 ng/L,  and the three acute-chronic ratios ranged from 1.734  to




5.421.  A freshwater alga was affected at a concentration of  1,220  ng/L.



A BCF of 1,410 was obtained with the fathead minnow.



    Acute values for 2,4,5-trichlorophenol  are available for  eleven saltwater




animal species in ten genera and range from 492 ^g/L for the  amphipod,




Rhepoxvnius abronius. to 3,830 MgA fฐr tne mysid,  Mysidopsis bahia.   The



six most sensitive species include three crustaceans,  two fishes,  and  a



polychaete worm and their acute values are  all within a factor of  1.8.   The



only saltwater species with which a chronic test has been conducted is the



inland silverside, Menidia beryl 1ina.   The  chronic  value is 38.68  pg/L,



and the acute-chronic ratio is 42.92.   The  saltwater diatom,  Skeletonema



costatum. was affected by 890 Mg/L-  BCFs determined with the inland




silverside ranged from 47 to 71.








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 aquatic organisms and their uses should not be



affected unacceptably if the four-day average concentration of 2,4,5-tri-



chlorophenol does not exceed 63 ng/L more than once every three years on



the average and if the one-hour average concentration does not exceed




100 ng/L more than once every three years on the average.  Because



sensitive freshwater animals appear to have a narrow range of acute




susceptibilities to 2,4,5-trichlorophenol,  this criterion will probably be as




protective as intended only when the magnitudes and/or durations of




excursions are appropriately small.

-------
    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, saltwater aquatic organisms  and their  uses should  not  be



affected unacceptably if the four-day average concentration of



2,4,5-trichlorophenol does  not exceed 11 ng/L more than once  every three



years on the average and if the one-hour average concentration does not



exceed 240 ng/L more than once every three years on the average.   Because



sensitive saltwater animals appear to have a narrow range of  acute



susceptibilities to 2,4,5-trichlorophenol, this  criterion will probably  be  as



protective as intended only when ฑhe magnitudes  and/or durations of



excursions are appropriately small.








Implementation



    As discussed  in the Water Quality Standards Regulation (U.S. EPA 1983a)




and the Foreword to this document, a water quality criterion for aquatic life



has regulatory impact only after  it has been adopted in a sttate 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



1983b,1987).  In  each standard a  state may adopt the national criterion, if




one exists, or, if adequately justified,  a site-specific  criterion.




    Site-specific criteria may include not only site-specific criterion




concentrations (U.S. EPA 1983b),  but also site-specific,  and possibly




pollutant-specific, durations of  averaging periods and frequencies of allowed




excursions (U.S.  EPA 1985b).  The averaging periods of "one  hour"  and "four
                                       10

-------
days" were selected by the U.S. EPA on the basis of data concerning how




rapidly some aquatic species react to increases in the concentrations of some




aquatic 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 1985b).  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.



    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 1985b), 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 also available (U.S.




EPA  1985b,1987).
                                       11

-------
                                to
                                CO
                                en
                                            o
                                            CO
                                                        to
                                                        CO
                                                        en
                                                         a.
                                                        00
OO
en
 o>

 e
to
CO
en
10
CO
(71
                        10
                        00
                        at
                        to
                        CO
                        en
                                                                                                                                   CO
                                                                                                                                   en
                                                                                                                                   co
                                                                                                                                   en
                                                                                                                               -X  O
                                                                                                                                in —
                                                                                                                                o  ซ
                                                                                                                               -M  (ft
            a  -ป
                1ft  —
            e  o  ao
            ซ  -K  en
                                                                                O
                                                                                -a
                                                                                o
                         o
                        -a
                         o
            in  in   01
            I       w
            o    - .ปซ
            — 1 —   3
            O  GO  —
            c  a>  —
                                                            —      -O  DO
                                                            o  —•  e  en
         o  -~
         ซ   a
         &  u
                                            >o
                                            to
                                                                                                        a
                                                                                                        to
                                                                                                                    00
                                                                                                                    to
    in
a  u
m  ui
                                            a
                                            to
                                            to
            CM
            *ป
            10
                       ei
                        a
                        10
                        OO
                        IO
a
en
o>
                        o
                        u
                        a.
 I
LD
 u

 M
 O
                 in
                 a
                 u
                 a









_
-•••ป O

^ . cy
3 a a
-o • a E
00. k.
— ^ (ft fl> O

o o| o e
1- l_| -0 .=
Tป -O 00
>• ป4 — 0
x z| ซj o
(rt
3

O
C
a

.a
3
^

O

e e
a .c
u o
a 0
W ^3
0 0
O L.
E

-•••. _•
<- o
^H ^
3 3
•o a>
0 (ft
— ป e

•w (ft
a 3
a. i.
— o
.e E
a. E
E o
< 0
0 —
(A
a
.^
o
e

- .~
- CL — U
—— (ft ••- 0

a. o

ป -0
e ซ
••H* ซ^
^
>ป O
— o
>• o
0 ซ
a —i
a

o a
i,^.,* ซ,•
a
•V u

— • u
D) -0
e E
C 3
•< — 1
^ ••
.- • c
e o>
O * tfl
> a e
3 •—ป — •
•—1 ~— ซ
- - .ซ
k.
^ 4)
3 e
o -o
w hป
•^ *~>
o
* a
E
* o
O u
e a
e
•~> in
e <ป

•o o
o ox:
.A at a> a
-s f f 1
o ol o .—
oe tซ| u. a.
_ g
0> ^
0
a —
IO 3
U
a —
i -^
a ป
^f W

a o
•w^* •ซ

a. u
3 O
t? ^L
*-^ O
o> ^
0
o —
10 3
U
a —
i ••-
a a
*ป I.

a o
-~r • —

Q. u
a. ซ
3 O
C2 n
                                                                                      12

-------
                                             CO
                                             Oป
                               CO
                               01
CO

0>
                                                                                                                          vป
                                                                                                                          9
                   CM

                   00
                e  CO     ซ-
                                                         o
                                                         9
               tn  —
               O  9
               jt  in
                           o
                           o
                                          •<
                                          0.
                                                                                           o
                                                                                           o
                                                                                                          OO
                                                                                                          en
                                                                                o
                                                                                o
                                                                                               O

                                                                                                9
0
o
               oo
               *r
               en
o
in
                                         10
                                         a
   in  -j
                          a
                          U1
                          CO

                          ^^
                           I
                          *ซ

                          
a
js in
w *^
>• 0)
— u
O 4)
Ck. Z
>
•o o
•—
— I/I
9 3
e —
c •—
0 J=
— a
.e o
k. —
^ O
in
.^
- c
o

- -c
-~ o
^* ^>
ซ•
3 in
^9 *^
o in
~^ o
0
•a -o
fmf ,mf
in in
^ >
a a
'^k O
•*. k.

3 O
•o
0 V>
•^^ 3
•_
•w e
0 >
Q. X
•^ O
-c a
a. 41
E -=
ซ ce

- 0
. , *^
•*- 9
— 3
3 a

a, o v>
E 4>

k. — 4>
ซ O e
in E o
k. E
VI 9 4)
V) •ซ- O
0 C —
k. — 0
o — a.
o

• 9
^•^ 3
-^- a

a. 3 in
g -0 41
— O f
k. 4>
j: 91 c
V) C O
— E

VI v O
o o —
k. E o
C4> ซ^i^ Qป
a.
g

t.

w o
e
ซ - 0
Q. — ป -0
.—  "^
o a e
o •— i o
o -ป••• 
-------
                                                                      in
                                                                      0
                                                                      0


                                                                      U
                                                               0

                                                               u
               0
               I.
               0
                       o

                       — 00
                       0 IX.
                       .— l/t
                       0
                                      •o
                                       B
                                                                                           I
                                                                                           o
                                                                                                                                                    o
                                                                                                                                                    CX
       0
       0
       in  if
       0

       u  •ซ-
       ซ  a
       a.  u
to
to
a
to
to
to
in
us
to
to
                                                                                                                 o
                                                                                                                 u
                                                                                                                 o
                                                                                                                  I
                                                                                                                 CO
           in  -i
       so,
       in  ui  0
       u
a
10

 0  a  o

0 10 to
^ tO VO
ซ m in
.
^ป










ซM o a














333

...
 l/t bt












V)
0 3
•0 0 L.
— U 0 VI
in c ••- 3
I. O O Q —
0 — — 0 3
> tป X •ซ-
_ .- -0 0 0 0
— • e e .e — • ป >
ซ) . — . 0 0 0 • — .
0 E in vi in 0 in
U — - 0 — >
.— — o u —~ ซ- -e — k.

C 0 -O *_ _ TJ • — 0 O.
0 > .— — 3 O — > O
— 3 C U -0 E en 3 l_
-^ .— , a o o ฃ c •— i o






t>
0
a
in
o
0
8
c
a
u
=
.
^^
0
*•
in
o
0
S

u
X
j=
01

o
.e

1
•
o

i^

u

i^

. .
—
o
0
e
0
L.

u

ce

. .

1
00
•
fs.
ซM

^_
0
e
o
._
.^
o
^_
^.
e
0
u
a
o
u

0
^

ฃ•
O
Q.
3

^
0
in
0
.a

-
. *
o
a
u

^^^


"o>
Q.

*ซ

CM
CO
e
••B
e

e
o
0
•o
0
^B
O
E
.^
in
0

in
o
*
VI
0
.ซ•

in
'^
ซ.

e


0
k.
3
in
o
a.
X
0
a.
<^
i—
i
in
-

.
CM

^_
V)
0
-c
91
•^


0
-C
I—

u
























^M
0
0
e
e

o
o
^B
V)

0
r—
^.

c
.^

^3
0
3
in
a
ซ
E


Q
U
t—
1
CO
.
rx.
-
"i

CM

(•.
O


~Si
n

to

^_
*
e
•ซ
o

e
o
o
^
V
^
o
ฃ
"^
VI
41


L.
•3
V)
O
a.
X
4)
a.
o
h—
1
i/)
-

•
CM

.+_
V)
4)
XI
91
• "•


4)
.^
1—

-o
























_.
O
ซ
o
E

"J
o
^.
V)

4)
f—
•*••

e
..^

^
4)
3
tfl
O
4)
E

a
^
tj
^_
i
00
.
rs.
•
^o

(M

U-
0


^Sป
Q.

O

00

e
.^
o
•+-
c
o
o
TT

-

-
CM

•+—
V)
4)
j=
9ป
•^


4)
-C
h-

4>
























__
0
0)
a
ฃ

u
O
•*•
VI

0)
_f^
-*-

c
.—

^
4>
3
tfl
O

-------













^.-t
**9
41
3
a
—
0
u
^^



^.

0
^.
^
a
ras estimated to contoin 41.6 pg/L of 2, 3, 7, 8-TCDD , bosed upon the concentration
W

VI
'ฃ
"*•
—
3
VI
O
a.
X
a.
o

i
in
^r
CM
...
v>
41
-C
en
*.
j=

0
-c
ปM


U
O
8

u
0
9
•*•
e
.w
-9
3
VI
O
Of
e
a
2
i
CO
•
rs.
•
ro
K
CM

^_
O

e
o
0
u
e
*
e
o
u
m
o
3
VI
o
.0
0
0
r—
00
O
en
cn
e
o
e
o
o
|
VI
VI
o
in
ซ

in
j^I
*•
~
u
3
VI
O
Q.
CL.
U
p—
1
in
^r
ซM
^.
in
9
^i
en
•_
^5

01
*•
|_


0
S

u
o
.
•"
e
•_
-e.
3
in
O
9
B
ea
2
i
to
•
r*ซ.
*
ro
•

U
3
in
o

8
a
s
1
00
•
rs.
•
ro
ป
CM

i^
O

lO
cn
0.
UJ
a
en
0
m
to
o
en
e
o
VI
3
O
VI
X
Ck
in
3
U
3
O
3
U
e
o

VI
9

U

*

ซ...
0
o
•*•
9
_..ป
3
O
U
c
._

T.I
9
V)
3

4.
O













a.
^B
O
e

--^
9>
a>
ซ...ซ>

>>,
^_
..
e
....
ซ_
o


15

-------
                                                 U3
                                                 oo
                                                 0>
                                                                                     a
                                                                                     u.
                                                                                    a.
                                                 Ob
                                                 I/I
                                                                                     01
                                                                                     3



.
ซ•
a
o
<.

•
0
.a
c
..
0
ae
o
	
^
V
c
•o
._
e
0

o
E

o
i/>
- E
9 O
0 u
e a
e
ฐi ซ

•o o
a -=
41 a
JZ 4)
-^ E
o •—
u. a.
 a   —
—   e
 e   4>
                                                                                              Ifa

-------




























o

^m
0


w
(—
g
o
k.

o
1

m
a
u









.^^
"9
41

e

^
e
o

- _j-



CM

V
,^
-a
9
h-


o

^—
9
^? ^f *^
0> M^ C4 C^4
(M Nป, ^ Cfl

QC f-ป *_ M* -^






ft
•J

9 ^ ~

^^
O 9

— fcp
a

—



OO


OO Ot 'O OO
C^4 ^f *O l^
irt ซ• *"*^





**





9

•M *™
O — J

O
• 3,

^

^J



CM o oo a
^F 'O *f* ซ^
r^ CM rsi 10
. . •
ซ!• MH ซ^







0ป <71
rs. rป.
Xl 1 ID I

*• . ^ *o
^^ ^ป P^ *O




VI
O O -
— _ ซ 0
J3 ซ -0 C
3 ._ .ฃ._._
-o - i. ป o in —
*- ซ Ok. h. —
O 3 C C CM ซ >
- — O*Q C > L.
e e ut_ — v> — ซ

t- oj o — ซ

^
,M
u

e
^
ซ 0 • 01 TJ 0 O
ซ •ซ O O -C -0 —
oo j3 o ซa = -o
•o •— e E JS ซ o —
ow .-— ซ.g — e
— ซ oo o— eซ
oo ae h^o. — • a
c -o-o











































































-oo ซ ซ ซ ซ
c -o -a M -a ซ
O 1/1 ซ O O
o. w o -a 0.0
"i 10 a -^ —
v/1 ^ Q -9 al -9 >1
— O ซ ซ — ซ —
0 — 6 <_ซ.—<ป
C Q t/l O>-ป O>
ซ E 0 6—0 E —
-C  ป VI 9
k> •— O 1 9 O^ •*- 4) *y ^~
V O -ป- fc- OC) CAO V)9

o -ซ k.e^ t. u, ub.k.
*B O •*• • - 9 ^tf 4) 41
trt — G O •""ป B-W ป - ^-
I uซe- -JO —40
9 -^ 0 O 
— in o*— oป3^ 9>?t.jซ
— - U Q. ป . ^^^ ^v ^ C3 G3 -^ OO^^-
— .  e ^r
o *•-<*;-•— *o — -^ o>
* O h- ^ -^- -9C -9Cf
— • - o e o "9 c o -N.
11 (A CM ป_ 999
c e ••• oo k. O e
t/i o .-.*.ซ incaa mua —
ซJ *— X 9 * • -. {A • _
Ul •*• O U ซ-9CM-^
O *^ ^" C ^~ O ^ป 9
u -o e o ta.oS *— o u.
A -^ 1 9 u O O 3
— C O, M Vป O W (rt
u • i o e (AGO tneo
>- u o L. o coo coซ
u e NO.O. o — H- o •— E
I o e 3 — •*- I — •*-
ซ U * 

— ซ '-90CA ^-"e- ^-"Sh- — 3 k."*"-a ซo- ซuoo o to o "^ •— CkO(A d CJ fM O •*. -^ — C. Cปh*C Q h— k. ซ(A-*-ft O t O Otซ— o *Q ^- ซ (j ^- H-m— i— u-J o 0> 1 ซ 9 1 • ••- 1 - ซ V} OO9O.6 CO ^T 9 CO*tf(A — • 9 * k. (/) • - kซ - - C u -A h*. * * j< f*ซ- CM •*- K. CM o ป - ป k. U -C ... U * *O O ^O ^— 9 'O ^— •*— t W . _J - *. - O O -O9 * O CM e CM k. w- 9* •"*. -^ O -^ ^ — (A Eo.9>* Eeo gee — • •*ป 3 3, .^ 3(V 3V4) M a — • 10 — 9 o •— ฎ G (A XO^C XWO. Xk.O (j 0> O — f-* •— 90.3 90.U —i as a a a o -a w -9 9 17


-------
u
M a *•
a a o
— ai u u
— jt a
a in ซJ —
at 014.
— a a
u u ~ at
— a a
c a. u
a 1/1 ซ






^> ซ•

1 I 04 I •* | | | ,

••O Ul
u
o
1
a •
ซซt a a
ซ "a —
a — a a
 ex <- o a was
M ,' S 0 — _ ซ l_ .-
a ^ 33 • a o, u -e o
— ฃ W*V • O (A O 03
ป 2 fl *• ฐ eajo i-a
r! - al a - •ซ. e .— tn u ซ
a =!Bo|i.ee —  -a 3 o a
ซ r* o Si o J: <•• ซ _ . e .
a in
w ซ

u
a a
a wi
~u OV.Q o. — — . a —. -oซ
aa *-. ao in *9a -JB *va — • tn a3

o c ป•— oe o ol aa — o — u o> 6 — o
t>.f a. u -o •- i- M j; 41 i— ป. ซ ji ซo ^ g
oo o. 41 o i- -o -ol ซ*8 a>Q e C 30 a.1
— 0 3 O — ซ *• >1 O.— O ซ S3 —41 6 a
u o O a. ww z ^| i^, a. a -j •ซ -j oa _j < o
M
a
a a
u • a
-a a "m —
'} -3 " * ^
'a a ซ. a
at • a —
• a u
o ซ



aoocMOoacM — aio
ua^^^ior-, — in~i
tAO>ps,POCMtOt0^rpo
ซ • • • .
CM ^ ^ — •*






^

rs.

^



a

O4










< —
- W
•*- cw
3 e
O *9
W W

o

o
•a o
e E
a o
oe vi





a
rsi


18

-------
   -c  ol
V)  O  —
41   I   —I
                                                       a
                                                       tO
                                                       tO
                                                                                                  10
                                                                                                  a
                                                                                                  as
u
UJ
^
Jp
ac
u
H-
<
9
h*
j
<
(/>
V)
3
9
O
f
O
.O

V)
.—
V)
a
• o
•o -o
.ซ ._
V) VI
ปป >
31 2
O
o
L.
- >
•O O

— • V)
ซ a
c —
c >
0 J=
.— o
.e o
u e
i. •—
-< ca
V)
3
* O
• 0
O 0)
e .—
e fc_
— o
6 >

"O C
0 O
ซ *0
JS O
VI C
a. ._
0) k.
ซ a
.ฃ >
 u

-_, t
 —
u. ^
ซ >
> u
-• Q>
.— .a
V)
o
•w —
e -o
o —
— e
e ซ
— a
.f-f
VI
U 0
0 ._
> -o
^ t.
— e
V) ซ
E
o
— o

e -v
a •-
— e
•^ ซ
< a
•3 ^
^ .—
E 3 (_
i_ o| .= ซ
o in
• c
ซ
ซ i-

4> >

j= in
0 —
ป 0
_• w
O 41
o. z
V) 0
a. in
E ซ
— —
l_ 41
f e
V) 0
E
in 4>
in o
o —
i. 0
O Q-
c
ซ 0
a. -o

L. in
•^ 3
in —
0
e Tป
a e
a o
u a.
in
3
- 3
ซ —
— 0)
O >
in
tn
^ >
in .e
— o
— 0
o> i-
e o
Ul Q-
M   ซ
3  —
e   a
41   u
                                            a
                                            03
                                            10
i   5
    in
                                                                      19

-------
















































^^

41
3
C

*t
e
0
u


I")


^^
A
9
t—
m
o
ซ


in
9

u
9
5>



g
o
4)
^
M

U
41
I/I



























_
o
V
31
VI
3
ฃ

o










u
•
o

jf
u
1
o

9
U




ซ
3
™J
9ป

ซ
3
a




























a

e
9)

3

ซ— -o — o
— o .ca
u E ex 9
o 1 E J=
a. ซ < ac







^n

q








lO CM
lO (71
m v









^
e
o
oe



CM —



9
3
^ซ
0
3*
9
3
y
*
C
0
3
VI
3
C
0
e
o
•o

VI
o


5
._
.^,
,^
VI
e
9
V) -J

— . Ol
8 *
S CM
O 91
-•- ai
^_
4*
e u
o
•ซ• 0
VI 3

VI 0

U
9

VI 3
O u
e • •<
— CM
S —
099 0
b. — — e
00 4) l_

9 O
--88 •
e o o
o u u ^
ae u. u. vi
ซ
o -a u u.









d
Of
a.
a
10
cn _j
Of
ป a,

^*ป X
"^ "^ *^
~~. 9 II
01 0
a. M o

(M —

oป o "ฐ

*_ป ซ
• ^i^
u "> ^
^•^
e u o>
o a.
— o

0 -ซ-
U 0 0>
<- oe oป
C •!" *
ซ o — • '
u •—
e e u
o o
^^ ^ 9
.= 3
a ซ-> —
3 1 O
6^3.

X 3 U
O O —
a ซ e
o
e — . u
o o .&
— a o

9 Uto -M
.^ O
— C
i tZ u
9
^m
o
m

+•
~
o
t/1









ซJ
0ป
3.
•w
to
fO
CM

II

CM
~ ^
ป^,
en
a.

9)

CM
rs.
^
ซMป

II

S
—t o

91 •ป-
. c
CM 9
1*. 0
ปป e
o
u (^

o 6
a a
— €
o •—
ป X
o
ซ a

3 C
U O
< .—
^
— 4)
O **
C '^
U. 0

























X
1)
*•
o
V
V)



Csl
O)

rป4
ซซr

u

o
.—
0
oe
u
.—
c
o
u

u
t
o>

3
(J
<

o
e

u.
























— j
cn
5.


X

cn
Csl
PS.
^f


II

0
3
—
a
^

u
•-B
e
o
u
-c
<_>

—
o
c
LA








20

-------
                                                                              co
                                                                              hs.

                                                                              O)
                   u
                                                                                  3

                                                                                  O
a  —
in   ซ
                                                     a.
                                                     VI
                        1/1
                        UJ
                        ae
                                                                            e
                                                                             a
                                    E

                                    t.
o
0
etonemo
ซ
^*

&
3
O
vt
o
o
o
o
Q
etonemo
ซ
-M
t^)
E
a
M
O
U
                                                                                                     VI


                                                                                                    o
                                                                                    21

-------
a
CO
K.
— 13 OO
41
o
e
41
I,
01
41
Of
a ea>
a —

a in —

_ JS ซ
0 3 *-
<_) SO.


41 ซ
." **
•M U
a o
1 5 w.
.2 * -



O)
•0 1
M^

g
01
o _

— o-a
"o u. ซ
rs.
a i
T ^
O* flO —
x.
A
-. an
o 41-0
• u —
a u a
JB 01 —


_
*
*• *• — ' ซyป "*~
ฐ S ฃ
o 53 ~*
! * I
ฃ *
i 1
2 • ^ ซ • „.
^* O "9 H- O tป
J -CO < J= 0
* k—

.— e o

a a —
!•ป

ao ซ
CVJ
3

^
w c*4
e i *ป -o
ia ซ i a

"ฐ
Ul , •*-
41 ^_
2 e ^
a o 6
^K ™"
'i ^!
a
u u
• ซ
41 C
u ft
^
e c
u —




fo l/l
1
^
**1
^




in
o
— a> o
a -a e

• o to —
0 W k. —
CO 01 >
c > *-
— ซ — ซ
g a •- -a
i/
4
t
0
e
1/1
•99 9
0 J= T3 —
0 a e "o
JS 0 9 • —
•s .s c s
1 u. a. — 3

o
e
0
^s
a.
o
u
O

u
•~
1
tn
~
0

V)
e
o
^
9
L.
c

e
o
ซ
3
VI
ซ
6
e
0

*
o
*
k.
9
aa
en
o
9
*•*
C
O
"~
— 9
o —
0 S
js a
tik U
0 U
o o
""" J3
ซ
i. e
^- 9
1
l/l — 1^'

ซM CO
•ซ^
te_
O H
u
c o
o — •
— u
+- 0
9 •—
*-
•^ e
c o
0 .—
O ••—
e 9
O L.
U •*•
e
•^9 0
0 U
U C
a o
9 9
0 • —
3 CO
9 J3





























































9
3
(ft
Vt
.—
*-

e
.—

•^
c
9

k.
^J
9
B
e
•"















crt
"9

Q.
•^
^^
c

U
0
GL
0
JS
ป.
W
u.
5

e
9

U.
0
CO
JS
91
e
'
-
•o
•—
^
1Z

^.

•2

a
._
—
E
o
e

ซ
u
•
in
u
o
u
o
(^

49
j:


-
0
^
^
• ••
in
in
o
a.

e

-------
0>



 o
                                                      03
                                                      o>
                                                                  m
                                                                  Tl
                                                                                         o
                                                                                                     in
                                                                                                     e
                               o

                               o
                               o

                               Ol
                               e to
                               3 9t
            o

            3

            •o
            c
            o

            o>
            e
            o
.-  lO
 >  OO
 ซ  en
            o

            ฃ -O
                                                                                                    -c  en
                                                                                                    OO  —
                                               in
                                               o
a
91
            u

            s  J
                                                      a
                                                      OO
                                                                      a
                                                                      a
                                                                      a
                       a
                       a
a
a
                                           e  —
                                           o   ป
o

in
                               a  o
                               -o  L.
                               ซ  o
                               a
                               a  e
                                                                  a  o
                                                                             a   o
                                                                                         a
                                                                                         in
                                                                      a
                                                                      a
                                                                                                         a
                                                                                                         m
o

e
                                          a

                                          PS.
                                                           i
                                                          00
                                                                                                     a

                                                                                                     00
               4)
               a
               1/1
a

o
•w
•_
o
e

u
a
o
^^
^n
4)
U
O
ซ.
j;
O
0

o
^
...
0
e

a
a
—
_^
a
- k_
o o
oป — •
— J=
^ *J
.2
'i

o
^_
._
kป

o
e
- e
e 4>
e E
o ป
M ป—
0 0
•ป- k.
O H-
k. 41
a. i—
41
E
3
^
VI
.ซ
wt
e
3
u
e
._
- k.
-~ o
— in
o in
e o
OO Lta
o
u

0
41
G
3
(/)
- O
— • "O
— 3
a 4)
e v>
oo a.








,1
o E!

4> a
u ••
0 e
iy ^g
9 a
— o
0 0
0,
ID
L. ^
V *— '
e
•^ •*-
— 0
O L.
of *•

ol e
3 S
0 U
00 1 03
O
•ซ•
o
—
-— *. u
o —
o
•*"
3
U
•*-

O
o
(/^
6 *.
ซ
I
CM 0
ซw •—

a. u
a. ซ
3 O
o **-
(A
9
-^ O
^H L.
3
CM O
V)
.ฃ 3
V) • —
•— V)
w- V)
•o o
O a
0 0
                                                                                 23

-------
4)
u
c
ซ
L.
41
                •o  —
                a
                O  VI
                .a  —
                •—  a
                                o  co
                                o  at
 O  00
 O  O>
 O  00
 a  01
ae  —
                a
                a
                               a
                               a
                               01
a
a
a
a
a
a
                                —  a
                                o  u
                                    0)
        
3

L.
* flj
E -*•
3 U
— O
L. ^
ซ o
^" ^—
u 0
a f
aa a.
T> " 3
a. in
E
3
ซ
U
O
j:
o
in
o

a
S ป
u a
^ e
V) O
E
V) ซ
M O
O — .
U 0
o a.
o. o tn
E ป
Z — . ซ
.= o c
ซ g o
C E
in ซ ซ
w •ป• o
o c —
1_ .- O
o • — a.
a. -o vi
g 0 ป
i_ — ซ
jr — . c
in o o
E E

-------
                                  REFERENCES








Ahlborg,  U.G.  and T.M Thunberg.  1980.  Chlorinated phenols:  Occurrence,



toxicity, metabolism, and environmental impact.  Crit.  Rev.  Toxicol.  7:1-35.








Anonymous. 1976. On 2,4,5-trichlorophenol and TCDD.  Naturwissenschaften




63:477.








Batte, E.G. and L.E. Swanson. 1952.  Laboratory evaluation of organic compounds



as molluscicides and ovocides. II. J.  Parasitol. 38:65-68.








Battelle Ocean Sciences. 1987. Acute toxicity of 2,4,5-trichlorophenol  to



saltwater animals.   Report to U.S. EPA Criteria and Standards Division.




Battelle Ocean Sciences, Duxbury, MA.








Benoit-Guyod,  J., C. Andre and K. Clavel.  1984a. Chlorophenols:  Degradation



and toxicity.  J. Fr. Hydrol.  15:249-263.                    ;








Benoit-Guyod,  J., C. Andre,  G. Taillandier, J.  Rochat  and A.  Boucherle.  1984b.



Toxicity and QSAR of Chlorophenols on  Lebi stes  reticulatus. Ecotoxicol.



Environ.  Saf.  8:227-235.








Blackman, G.E., M.H. Parke and G. Carton.  I955a. The physiological  activity  of



substituted phenols. I. Relationships  between chemical  structure and




physiological  activity. Arch. Biochem. Biophys. 54:45-54.
                                       25

-------
Blackman, G.E., M.H.  Parke and G.  Carton. 1955b.  The physiological  activity of



substituted phenols.  II. Relationships between physical properties  and




physiological activity. Arch.  Biochem. Biophys.  54:55-71.








Bringmann, G. and R.  Kuhn. 1982.  Results of toxic action of water pollutants



on Daphnia magna Straus tested by an improved standardized procedure.  Z.



Wasser Abwasser Forsch. 15:1-6.








Buccafusco, R.J., S.J.  Ells and G.A. LeBlanc. 1981. Acute toxicity of priority




pollutants to bluegill  (Lepomis macrochirusK Bull. Environ. Contam. Toxicol.



26:446-452.








Buikema. A.L., Jr., M.J. McGinnis and J. Cairns,  Jr. 1979. Phenolics  in



aquatic ecosystems: A  selected review of recent  literature. Mar. Environ.  Res.




2:87-181.








Call, D.J., L.T. Brooke and P.Y. Lu.  1980. Uptake, elimination,  and metabolism




of three phenols by fathead minnows. Arch. Environ. Contam. Toxicol.



9:699-714.








Devillers, J. and P. Chambon. 1986. Acute toxicity and  QSAR of  chlorophenols



on Daphnia magna. Bull. Environ. Contam. Toxicol.  37:599-605.








Dietz, F.  and J. Traud. 1978. Odor  and  taste  threshold  concentrations of




phenolic compounds. Gas-ffasserfach  119:318-325.








Doedens, J.D.  1964. Chlorophenols.  In:  Kirk-Othmer encyclopedia of  chemical




technology.  2nd  Ed., Vol.  5.  Wiley  and  Sons,  New York,  NY.  pp.  325-338.





                                       26

-------
Dojlido, J.R. 1979. Investigations of the biodegrabi1ity and toxicity of



organic compounds. EPA-600/2-79-163 or PB80-179336. National Technical




Information Services,  Springfield, VA.








Durhan, E. 1986. U.S.  EPA, Duluth, MN. (Memorandum to R. Spehar, U.S. EPA,




Duluth, MN. June 18).








Firestone, D.,  J. Ress, N.L. Brown, R.P. Barron and J.N. Damico. 1972.



Determination of polychlorodibenzo-p-dioxins and related compounds in



commercial chlorophenols. J. Assoc. Off. Anal. Chem. 55:85-92.








Hansch, C. and A. Leo. 1979. Substituent constants for  correlation analysis  in




chemistry and biology. Wiley, New York, N.Y.








Hattori, M.,  K. Senoo, S. Harada, Y.  Ishizu and M. Goto. 1984.  The Daphnia




reproduction test of some environmental chemicals. Seitai Kagaki 6:23-27.








Hattula, M.L.,  V. Wasenius, H. Reunanen and A.U. Arstila. 1981. Acute toxicity



of some chlorinated phenols, catechols, and cresols to  trout.  Bull.  Environ.



Contain. Toxicol. 26:295-298.








Heitmuller, P.T., T.A. Hollister and  P.R. Parrish. 1981. Acute  toxicity  of  54



industrial chemicals to sheepshead minnows (Cyprinodon  variegatus).   Bull.



Environ. Contain. Toxicol. 27:596-604.








Hosaka, Y., J.  Hashiguchi, Y. Sakata, E.A. Banez and B.L. Bias. 1984. An




assessment of the molluscicidal activity of 8-2 and some other chemicals




against Oncomelani a quadras i. Jpn. J. Parasitol. 33:55-58.




                                       27

-------
Huang,  J.C.  and E.F.  Gloyna.  1967.  Effects of toxic organics on photosynthetic



reoxygenation.  Center for Research in Water Resources,  University of  Texas,




Austin, TX.








Huang,  J.C.  and E.F.  Gloyna.  1968.  Effect of organic compounds on



photosynthetic oxygenation - I. Chlorophyll destruction and suppression of



photosynthetic oxygen production. Water Res. 2:347-368.








Hughes. M.M. and R. Pruell. 1987. U.S. EPA. Narragansett,  RI.  (Memorandum to



D.J. Hansen, U.S. EPA, Narragansett, RI.)








Jolley, R.L., G. Jones, W.W. Pitt and J.E. Thompson. 1978.  Chlorination of




organics in cooling waters and process effluents.   In: Proceedings of  the



conference on the environmental  impact of  water chlorination.   Jolley, R.L.




(Ed.).  CONF-751096. National Technical Information  Service, Springfield,  VA.




pp. 115-152.








Kaiser, K.L.E.,  D.G.  Dixon and P.V.  Hodson.  1984.  QSAR studies  on



chlorophenols,  chlorobenzenes  and para-substituted  phenols.  In:  QSAR in



environmental toxicology.  Kaiser, K.L.E.  (Ed.). D.  Reidel  Publishing Company,




Boston, MA.  pp.  189-208.








Knie,  J., A. Halke,  I. Juhnke  and W.  Schiller.  1983.  Results  of studies  on




chemical substances  with  four  biotests.  Dtsch.  Gewaesserkd. Mitt. 27:77-79.
                                      28

-------
Kobayashi,  K..  H.  Akitake and K.  Manabe.  1979.  Relation between toxicity and



accumulation of various chlorophenols in goldfish.  Bull.  Jpn.  Soc.  Sci.  Fish.




45:173-175.








Kobayashi,  K.,  S.  Kimura and Y. Oshima.  1984.  Sulfate conjugation of various



phenols by liver-soluble fraction of goldfish.  Bull. Jpn. Soc. Sci. Fish.




50:833-837.








Kozak, V.P.,  G.V.  Simsiman, G. Chester,  D. Stenslay and J. Harkin.  1979.



Reviews of the environmental effects of pollutants. XI. Chlorophenols.



EPA-600/1-79-012.  National Technical Information Service, Springfield, VA.








LeBlanc, G.A.  1980. Acute toxicity of priority pollutants to water flea



(Paphnia magna).  Bull. Environ. Contain.  Toxicol. 24:884-691.








LeBlanc, G.A.  1984. Comparative structure-toxicity  relationships between  acute



and chronic effects to aquatic organisms. In: QSAR  in  environmental




toxicology.  Kaiser, K.L.E.  (Ed.). D. Reidel Publishing Company, Boston,  MA.



pp. 235-280.








McKim, J.,  P.  Schneider and G. Veith. 1985. Absorption dynamics of  organic



chemical transport across trout gills as  related to octanol-water  partition



coefficient.  Toxicol. Appl. Pharmacol. 77:1-10.








Nagabhushanam, R.  and D.P.  Vaidya.  1981.  Effect of  chemical agents  on the




early development of  eggs of  the  vector  snail,  Indoplanorbi s  exustus.  Riv.




Parassitol.  42:271-275.
                                      29

-------
Paasivirta,  J.,  K.  Heinola,  T.  Humppi,  A.  Karjalainen,  J.  Knuutinen,  K.



Mantykoski,  R. Paukku, T. Piilola, K. Surma-Aho,  J.  Tarhanen,  L.  Welling and




H.  Vihonen.  1985.  Pol/chlorinated phenols,  guaiacols and catechols in



environment.  Chemosphere 14:469-491.








Persson,  P.  1984.  Uptake and release of environmentally occurring odorous



compounds by fish.  Water Res. 18:1263-1271.








Rao,  K.R., F.R.  Fox, P.J. Conklin and A.C.  Cantelmo. 1981. Comparative



toxicology and pharmacology of chlorophenols: Studies on the grass shrimp,



Palaemonetes PUEJO. In: Biological monitoring of marine pollutants. Vernberg,



J., A. Calabrese,  F.P. Thurberg and  W.B. Vernberg (Eds.). Academic Press, New




York, NY. pp. 37-72.








Ribo, J.M. and K.L.E.  Kaiser. 1983.  Effects  of selected chemicals  to



photoluminescent bacteria and their  correlations with  acute and  sublethal



effects  on other organisms.  Chemosphere 12:1421-1442.       /








Rockwell, A.L. and  R.A.  Larson.  1978.  Aqueous chlorination  of  some phenolic




acids. In: Water chlorination:  Environmental  impact and  health effects.  Vol.



2. Jolley, R.L., L.H.  Gorchev,  and  D.H. Hamilton, Jr.  (Eds.).  Ann Arbor



Science  Publishers, Ann  Arbor,  MI.  pp.  67-74.








Saarikoski,  J. and  M.  Viluksela.  1981.  Influence  of pH on the  toxicity  of




substituted  phenols to fish. Arch.  Environ.  Contain. Toxicol.  10:747-753.
                                       30

-------
Saarikoski,  J.  and M. Vilukscla. 1982. Relation between physiocheraical



properties of phenols and their toiicity and accumulation in fish.  Ecotoxicol.



Environ. Saf. 6:501-512.








Sabourin, T.D.,  R.T. Faulk,  J.J. Coyle, G.M. Degraeve,  L.T.  Brooke, D.J.  Call.



S.L. Harting, L. Larson, C.A. Lindberg, T.T. Markee, D.J. McCauley and S.H.



Poirier. 1986.  Freshwater aquatic criteria development and toxicity testing.



Final Report to U.S. EPA on contract No. 68-01-6986. Battelle Columbus




Division, Columbus, OH.








Salkinoja-Salonen, M.,  M. Saxelin, J. Pere, T. Jaakola, J. Saarikoski,  R.



Hakulinen and 0. Koistinen.  1981. Analysis of toxicity and biodegradabi1ity of



organochlorine  compounds released into the environment in bleaching effluents



of Kraft pulping.  In: Advances  in the  identification and analysis  of organic



pollutants in water. Vol. 2. Keith, L.H. (Ed.). Butterworth, Woburn, MA. pp.



1131-1184.








Shumway, D.L. and J.R.  Palensky. 1973.  Impairment of the flavor of  fish  by



water pollutants. EPA-R3-73-010. National Technical Information Service,



Springfield, VA.








Spehar, R.L. 1988. U.S. EPA, Duluth, MN. (Memorandum to  D.J. Call.  University



of Wisconsin-Superior,  Superior, WI. Sept.  16.).








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.






                                       31

-------
Stolzenburg,  T.  and J.  Sullivan.  1984.  Dioxin - a cause  for concern?



WIS-SG-83-141. University of Wisconsin Sea Grant Institute,  Madison,  HI.








U.S. EPA.  1978.  Quality criteria for water.  EPA-440/9-76-023.  National



Technical  Information Service, Springfield,  VA.








U.S. EPA.  1978.  In-depth studies on health and environmental impacts  of



selected water pollutants.  (Table of data available from C.E.  Stephan,  U.S.



EPA, Duluth.  MN).








U.S. EPA.  1980.  Ambient water quality criteria for chlorinated phenols.



EPA-440/5-80-032 or PB81-117434.  National Technical Information Service.




Springfield,  VA.








U.S. EPA.  1983a. Water quality standards  regulation. Federal Regist.



48:51400-51413.  November 8.








U.S. EPA.  1983b. Water quality  standards  handbook.  Office  of Water Regulations



and Standards,  Washington.  DC.








U.S. EPA.  1985a. 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.  50:30793-30798.  July 29.
                                       32

-------