EPA-600/3-77-099
August 1977
Ecological Research Series
       A RAPID ASSESSMENT  OF THE  TOXICITY OF
                   THREE  CHLORINATED CYCLODIENE
                     INSECTICIDE  INTERMEDIATES TO
                                  FATHEAD  MINNOWS
                                    Environmental Research Laboratory
                                    Office of Research and Development
                                   U.S. Environmental Protection Agency
                                         Duluth, Minnesota 55804

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                RESEARCH REPORTING SERIES

Research reports of the Office of Research and Development, U.S. Environmental
Protection Agency, have been grouped into nine series. These nine broad cate-
gories were established to facilitate further development and application of en-
vironmental technology.  Elimination  of  traditional grouping was consciously
planned to foster technology transfer and a maximum interface in related fields.
The nine series are:

      1.  Environmental  Health Effects Research
      2.  Environmental  Protection Technology
      3.  Ecological Research
      4.  Environmental  Monitoring
      5.  Socioeconomic Environmental Studies
      6.  Scientific and Technical Assessment Reports (STAR)
      7.  Interagency  Energy-Environment Research and Development
      8.  "Special"  Reports
      9.  Miscellaneous Reports

This report has been assigned to the ECOLOGICAL RESEARCH series. This series
describes research on  the effects of pollution on humans, plant and animal spe-
cies, and materials.  Problems are assessed for their long- and short-term influ-
ences. Investigations include formation, transport, and pathway studies to deter-
mine the fate of pollutants and their effects. This work provides the technical basis
for setting standards to minimize undesirable changes in living organisms in the
aquatic, terrestrial, and atmospheric environments.
This document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia 22161.

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                                                  EPA-600/3-77-099
                                                  August 1977
A RAPID ASSESSMENT OF THE TOXICITY OF THREE CHLORINATED
CYCLODIENE INSECTICIDE INTERMEDIATES TO FATHEAD MINNOWS
                          by

                   Robert L. Spehar
                    Oilman D. Veith
                    David L. DeFoe
                 Barbara A. Bergstedt
       Environmental Research Laboratory-Duluth
                Duluth, Minnesota 55804
       ENVIRONMENTAL RESEARCH LABORATORY-DULUTH
          OFFICE OF RESEARCH AND DEVELOPMENT
         U.S. ENVIRONMENTAL PROTECTION AGENCY
                DULUTH, MINNESOTA 55804

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                                 DISCLAIMER
     This report has been reviewed by  the  Environmental  Research  Laboratory-
Duluth, U.S. Environmental Protection  Agency,  and  approved  for publication.
Mention of trade names or commercial products  does not constitute endorsement
or recommendation for use.
                                      ii

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                                 FOREWORD
     This report describes the toxic!ty of three  organochlorine  compounds used
as intermediates in the manufacture of pesticides.   The  U.S. Food  and Drug
Administration noted residues in fish samples  collected  below  a  pesticide
manufacturing plant and alerted the Environmental Protection Agency  for
necessary action.  This research demonstrates  the application  of current state
of the art methods to measure chronic toxicity and  residue  forming potential
in a 30-day test.

     A broad base of data accumulated over the past 10 years suggests
that the results of embryo-larval and early juvenile tests  with  associated
residue measurements will provide results within  a  factor of two of  the values
that would be obtained in full life-cycle chronic tests.


                                      Donald I. Mount, Ph.D.
                                      Director
                                      Environmental Research Laboratory
                                      Duluth,  Minnesota
                                      iii

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                                   ABSTRACT


     A rapid assessment  study  to  determine the toxicity and bioaccumulation of
three chlorinated  cyclodiene insecticide intermediates; hexachlorocyclo-
pentadiene, hexachloronorbornadiene,  and heptachloronorhoraene to fathead
minnow larvae and  early  juveniles was conducted for 30 days under flow-through
conditions.

     A concentration  of  7.3 yg/liter  of hexachlorocyclopentadiene caused
significant decreases in survival after 4 days.  Growth of fish exposed for
30 days was not  significantly  decreased at any of the concentrations tested.
The highest concentration of hexachlorocyclopentadiene having no adverse effect
was 3.7 yg/liter.

     Concentrations of 122 and 226 yg/liter of hexachloronorbornadiene caused
significant decreases in survival after 4 days.  Growth of 30 day-old larvae
was significantly  decreased at 38.4 yg/liter and was the most sensitive
indicator of toxicity.   The highest concentration having no adverse effect was
20.0 yg/liter'.   The average bioconcentration factor for fish exposed to less
than 38.4 yg/liter of this compound was 6400.

     Survival of fathead minnows  exposed to heptachloronorbornene was
significantly decreased  at 83.5 yg/liter after 4 days.  Growth was significantly
reduced at 40 yg/liter after 30 days  and was the most sensitive indicator of
toxicity.  The highest concentration  having no adverse effect was 25.9 yg/liter.
The average bioconcentration factor for fish exposed to less than 40 yg/liter
of this compound in water was  11,200.
                                      iv

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                                   CONTENTS

Foreword	ill
Abstract	' iv
Figures  ..... 	  vi
Tables	vii
Acknowledgments	viii

     1.  Introduction	   1
     2.  Conclusions 	   5
     3.  Recommendations 	   6
     4.  Materials and Methods	   7
               Water Characteristics 	   7
               Exposure System	   7
               Chemical Conditions 	   7
               Biological Methods	8
               Residue Analysis	12
               Statistical Analysis	12
     5.  Results	13
               Hexachlorocyclopentadiene ("hex") 	  13
                     Toxicity	13
               Hexachloronorbornadiene ("X") 	  13
                     Toxicity	13
                     Accumulation	13
               Heptachloronorbornene ("Y") 	  16
                     Toxicity	16
                     Accumulation	16
     6.  Discussion	17

References	19

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                                   FIGURES

Number                                                                  Page

  1     The manufacture of endrin from hexachlorocyclopentadiene
          ("hex"), reproduced from Barthel £t al. (1969)	3

  2     Relationship between LC50 (log scale) of hexachlorocyclo-
          pentadiene ("hex"), hexachloronorbornadiene ("X"), and
          heptachloronorbornene ("Y") to exposure time (log scale)
          for fathead minnows	14

  3     Residue accumulation (log scale) of. hexachloronorbornadiene
          ("X") and heptachloronorbomene ("Y") measured in fathead
          minnows exposed for 30 days	15
                                       vi

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                                   TABLES
Number                                                                  Page

  1   Survival and growth of fathead minnows exposed to various
        concentrations of hexachlorocyclopentadiene ("hex") 	   9

  2   Survival and growth of fathead minnows exposed to various
        concentrations of hexachloronorbornadiene ("X") 	  10

  3   Survival and growth of fathead minnows exposed to various
        concentrations of heptachloronorbornene ("Y") 	  11
                                    vii

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                               ACKNOWLEDGMENTS
     The authors wish to thank Mr. D. Tanner for making routine water analysis,
constructing test equipment, and for daily assistance; and the Environmental
Research Laboratory-Duluth's staff for technical assistance, advice and
manuscript review.
                                      viii

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                                 SECTION 1

                               INTRODUCTION


     The purpose of this study was to make a rapid assessment of the toxiclty
and bioaccumulation of three chlorinated cyclodiene insecticide intermediates;
hexachlorocyclopentadiene (."hex"), hexachloronorbornadiene C"X"), and
heptachloronorbornene ("Y") using larval and early juvenile stages of the
fathead minnow.  The latter two compounds have been referred to as "X" and
"Y", respectively, in the literature (Barthel ejt al., 1969}.

     The study was Initiated upon request for assistance from the Regional
Administrator, Region IV, to aid the U.S. Environmental Protection Agency
(EPA) in carrying out its responsibilities under the Federal Water Pollution
Control Act of 1972 concerning the discharge of these chemicals Into the
Mississippi River near Memphis, Tennessee.

     Results of a study by the U.S. Food and Drug Administration C1976} in 1972-
1974 indicate that significant amounts of "X" and "Y" along with an epoxy
derivative (a metabolite of "X") were found in edible fish from the Mississippi
River near Memphis.  The data showed that the most frequent occurrence and
highest residues of these chemicals were found In fish from the Memphis area
near a primary manufacturer of endrin and heptachlor, in contrast to low
amounts found in fish from other parts of the United States.  This agrees with
work by Barthel jst al. (1966, 1969) who found that pesticide manufacturing
operations near Memphis was a source of significant pesticide contamination
in the sediments and water during studies conducted in 1964, 1966, and 1967.
These results showed that high concentrations (parts per thousand) of several
insecticide residues and residues of "X" and "Y" occurred In the bottom
sediments, spoils, and flood plain deposits.

     In December, 1975, "hex11 was qualitatively identified as a contaminant in
the discharge of a pesticide production plant In Memphis (U.S. EPA, 1977).  In
May, 1977, "hex" was also qualitatively identified at a pesticide production
plant in Michigan.  Concentrations of "hex" were identified in the air, in the
plant's aqueous discharge and in fish tissue in the receiving stream.

     Hexachlorocyclopentadiene is the key Intermediate in the synthesis of
stable chlorinated cyclodiene insecticides including aldrln, dleldrln,  endrin,
endosulfan, heptachlor, chlordane, isodrin and mlrex (Brooks, 1974).  The
accumulation of residues of these insecticides In higher trophic levels has
been demonstrated by several authors and is presently being used as a guideline
for water quality criteria (National Academy of Sciences and National Academy
of Engineering, 1973).  Some other products derived from "hex" are nonflammable
resins, fungicides, heat resistant and shock proof plastics, acids, esters,

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ketones and fluorocarbons.  It is a clear, yellow, slightly soluble liquid that
is produced by two companies in the United States; Hooker Chemical Corporation
(at Montague, Michigan and Niagara Falls, New York) and Velsicol Chemical
Corporation (at Memphis, Tennessee).  Using the Diels-Alder reaction,
hexachlorocyclopentadiene can be transformed by the addition of vinyl chloride
to heptachloronorbornene and further converted by dehydro-chlorination to
hexachloronorbornadiene, a key intermediate in the synthesis of isodrin and
endrin (Brooks, 1974) (Figure 1).  The estimated production of hexachloro-
cyclopentadiene in the U.S. is approximately 7 to 15 million pounds per year
(U.S. EPA, 1977).

     The toxicity of chlorinated cyclodiene insecticides to aquatic life has
been studied by several authors:  Henderson e£ al. (1959), Mount (1962), Mount
et al. (1966), Mount and Putnicki (1966), Johnson (1967), Reinert (JL967), Brungs
and Mount (1967), Macek et al. (1969), Grant (1976), Cardwell Q977) and
numerous others.  These compounds and their metabolites have been shown to
accumulate in aquatic systems and are directly toxic to various aquatic
organisms at water concentrations of less than 1 pg/liter.  However, only
limited information is available in the literature concerning the toxicity of
these three chemical intermediates.  Cole (1954) investigated the germicidal
effects of a commercial "hex" preparation called P-162 in sewage effluents and
found that this chemical was more toxic to bacteria, coliform and Salmonella
typhasa than was chlorine.  Results showed that 10 mg/liter of "hex" reduced
bacteria counts by at least 90% in 2-hr while chlorine over the same time
period and concentration reduced the total count by about 45%.  Similar results
were observed with coliform and Salmonella at 5 and 10 mg/liter.  Davis and
Hardcastle (1959) determined the 24, 48, and 96-hr median tolerance limit
(TL ) of "hex" for bluegills (Lepomis macrochirus) and largemouth bass
(Micropterus salmoides).  The results of static bioassays for these time
periods were respectively, for bluegills, <500, 30, and 25 mg/liter and for bass
<500, 35, and 20 mg/liter (average water hardness, 77 mg/liter).  The toxicity
of "hex" to fathead minnows was tested by the U.S. Department of Health,
Education and Welfare (1956) using two dilution waters and two formulations
for preparing test concentrations.  The results demonstrated that (lhex" was
slightly less toxic in an acetone solution than in a water emulsion and more
toxic in hard water.  Recorded 24, 48, and 96-hr TI^ values in hard water
(emulsion) were 0.075, 0.059 and 0.059 mg/liter, respectively.  A model
ecosystem study by Lu et al. (1975) showed that "hex" has considerable
ecological stability and moderate biomagnification potential in algae
(Oedogonium cardiacum), snails (Physa sp.), mosquito larvae (Culex pipiens
quinquefasciatus) and fish (Gambusia affinis).  Studies reported by Mount and
Putnicki (1966) showed that the chemical intermediates "X" and "Y" and endrin
accumulated in all samples of fish dying in the Mississippi River in 1963.
Laboratory studies by these authors indicated that these two intermediates
were approximately 1,000 to 10,000 times less toxic than endrin to guppies
(Poecilia reticulata).

     Studies by Ingle (1953), Treon e* al. (1955) and Naishstein and Lisovskaya
(1965) have shown that hexachlorocyclopentadiene can produce toxicity in
mammals via ingestion, inhalation, or dermal exposures.  Degenerative changes, in
the brain, heart, adrenals,  liver,  kidney and  lungs were observed  in severly
poisoned animals by all routes of administration.

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                                     CH,-CHCL
                                  VINYL CHLORIDE
      "Y"OR HEPTdCHLORONORBORNENE
                                                        CYCLDPENTADIENE
*X" OR HEXACHLORONORBORNADIENE
                                                        BOOR IN
Figure 1.  The manufacture of endrin from hexachlorocyclopentadiene C"hex''l, reproduced
          ftom Barthel et al, Q9691.

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     No specific studies on human toxicity of these three chemical intermediates
were shown in the literature.  However, several inferences of the effects of
"hex" to researchers using these chemicals, such as eye irritation, headaches
and skin irritations were made by Ingle (1953), Treon e£ al* (1955), and Hooker
Chemical and Plastics Corporation (1969).  Taste and odor threshold concentrations
of "hex" in water were reported as 1.4 and 1.6 yg/liter, respectively,
(Naishstein and Lisovskaya, 1965).

     The study herein describes the toxicity and bioaccumulation of the above
named chlorinated cyclodiene insecticide intermediates in 30 day tests with
early life stages of the fathead minnow.  The use of short term toxicity tests
involving the early developmental stages of fish to predict chronic toxicity
has been proposed by several investigators (Pickering and Thatcher, 1970;
Pickering and Cast, 1972; McKim e£ al., 1975; Eaton et al., 1977; and McKim et
al.', 1977).  An extensive review of the literature (McKim, 1977) on life-cycle
toxicity tests with fish showed that embryo-larval and early-juvenile stages were
the most or among the most sensitive to chemical pollutants.  It was concluded
that tests utilizing these stages can be used to estimate the maximum acceptable
toxicant concentration (MATC) within a factor of two and should be useful in
screening large numbers of chemicals.

     The ability to predict the bioconcentratlon potential and steady state
concentrations of chemicals from relatively short exposure periods was discussed
by Blau et^al., 1975.  Hansen et_ al^. (1971) demonstrated that chlorinated
compounds such as PCB's were rapidly stored in fish with maximum residue
concentrations being attained in 14 to 28 days.  Thereafter, the concentrations
in the tissues remained constant with  continued exposure.  Consequently, the
bioconcentration factors reported in this study can be considered estimates
of what would be determined from longer exposures.

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                                  SECTION 2

                                 CONCLUSIONS


1.  Thirty day exposures with larval and early juvenile  fathead minnows  shoved
    that concentrations of 7.3, 38.4, and 40.0 pg/liter  and  above  of  hexachloro-
    cyclopentadlene ("hex"), hexachloronorbornadiene ("X"),  and heptachloro-
    norbornene ("Y"), respectively,  would be deleterious to  this species.

2.  Hexachloronorbornadiene and heptachloronorbornene decreased growth at  40
    pg/liter, 2 to 3 times lower than concentrations affecting survival.

3.  Larval and early juvenile stages of fathead minnows  under the  present  test
    conditions were more sensitive to all three intermediate compounds than
    this same species and other species tested for  similar time periods  in
    earlier studies.

4.  The toxlcity curve for "hex" showed that this compound was a non-cumulative
    poison.  A median lethal threshold was attained within 4 days.  Toxicity
    curves for "X" and "Y" indicate that these compounds had a cumulative  action.

5.  Residue concentrations of "X" and "Y" Increased with increased exposure
    concentrations up to a concentration causing decreases in growth  of  the
    fish.  The average bioconcentration factors for fish exposed to "X"  and
    "Y" were 6,400 and 11,200, respectively.  Residue concentrations  of  "hex"
    in fathead minnows were not obtained.

6.  A rapid assessment of the toxlcity of hexachlorocyclopentadlene,  hexachloro-
    norbornadiene, and heptacbloronorbomene utilizing 30 day tests with larval
    and early juvenile fathead minnows indicate that these compounds  may present
    a potential hazard to aquatic systems.  The bioaccumulation of hexachloro-
    norbornadiene and heptachloronorbornene in these fish suggest  their
    possible biomagnlfication in higher food chain  organisms.

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                                 SECTION 3

                              RECOMMENDATIONS


1.  Concentrations of hexachlorocyclopentadiene,  hexachloronorbornadiene,  and
    heptachloronorbornene not exceeding 3.7, 20,  and 25.9 yg/liter,  respectively,
    appear "safe" for fathead minnows under the conditions tested and may  be
    used as first approximations of non-toxic concentrations.   Concentrations
    may need to be lowered to comply with residue limits once acceptable residue
    concentrations are established.

2.  An assessment of the toxicity of these compounds to other aquatic life
    should be completed.

3.  Studies involving the toxicity of mixtures of these chemical intermediates
    along with mixtures of other toxicants, particularly the organochlorine
    insecticides for which they are used to synthesize, are needed to evaluate
    interactions.

4.  Since these intermediate compounds have been found in edible fish,
    investigations concerning what concentrations are safe for human consumption
    should be made.

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                                 SECTION 4

                           MATERIALS AND METHODS
WATER CHARACTERISTICS

     Unfiltered Lake Superior water was heated and used in all tests at 25+2
C.  Chemical characteristics of the test water were determined weekly according
to methods described by the American Public Health Association et al^. (1975).
Ranges for these measurements were (in milligrams per liter):  dissolved
oxygen, 7.2-8.6; hardness, 45-47 as CaCOa; alkalinity, 42-43 as CaC03; and
acidity, 1.5-2.5 as CaCOa.  The pH ranged from 7.2 to 7.7.


EXPOSURE SYSTEM

     The three tests were conducted with intermittent-flow exposure systems
consisting of a multi-toxicant injection system (DeFoe, 1975) which delivered
five toxicant concentrations with equal amounts of acetone (4 mg/liter) and a
control to duplicate exposure chambers.  The test chambers were glass aquaria,
45 x 16 x 18 cm, with a water volume of 8.9 liters.  Water depth was 13.5 cm.
Flow rate to each chamber was 500 ml every 3 min providing a 93% replacement
of the test water every 2.7-hr (Sprague, 1969).

     Flourescent bulbs provided a light intensity of 18-28 lumens at the water
surface.  An automatically controlled 16-hr photoperiod was used.


CHEMICAL CONDITIONS

     Chemicals used in this study were supplied by Velsicol Chemical Corporation,
Memphis, Tennessee.  Water samples were collected daily from the test chambers
by siphoning each sample through a glass tube directly into volumetric flasks
containing hexane.  Due to the differences in test concentrations, 500 ml flasks
containing 50 ml hexane were used in the test with "hex" and 250 ml flasks
containing 50 ml hexane were used in the tests with "X" and "Y".  All samples
were stirred for 1.5 hr at a speed great enough to cause rigorous vortex mixing.
The phases were allowed to separate for 1 hr and an aliquot of hexane was
transferred to a vial for gas-liquid chromatograph (GLC) analysis.  The samples
were analyzed on a Hewlett Packard 5730 H gas chromatograph equipped with an
auto sampler and Ni-63 electron capture cell.  The column was 1.8 m x 2 mm (ID)
glass coil filled with 4% SE-30 and 6% OV-210 on 80/100 mesh Gas Chrom Q.  The
carrier gas was argon containing 5% methane and all chromatograms were produced
at a column temperature of 150 C.

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     To estimate the precision of the GLC injection procedure,  six aliquots
of extracts from the next to the lowest concentration in each test were
transferred to vials for replicate analysis.   The results showed that the GC
reproducibility gave relative standard deviations of 9.8% for the hexachloro-
cyclopentadiene at a concentration of 0.67 yg/liter, 1.5% for hexachloronor-
bornadiene at 36.7 yg/liter, and 0.6% for heptachloronorbornene at 45 yg/liter.
It is generally accepted that GLC analyses should have a precision of approxi-
mately 5%.  Consequently, the precision of hexachlorocyclopentadiene analysis
is slightly less than many pesticide analyses and the precision of the other
analyses are well within the anticipated variability.  The decrease in precision
in the former case is likely due to the much greater volatility of hexachloro-
cyclopentadiene and the fact that the concentrations were a order of
magnitude lower than the other chemicals.

     The precision of the sampling and extraction procedure was examined
by analyzing six replicate water samples from a single tank in each diluter.
The results showed that the measured concentration could be estimated with
a relative standard deviation of 10.3%, 1.4%, and 0.9% for "hex", "X", and
"Y", respectively.  Since the variation of water analyses is typically less than
10%, these measurements are within acceptable limits.  Moreover, the variability
due to sample collection and extraction does not significantly increase the
variability of the overall analysis arising from the GLC injection.

     Measured concentrations of each chemical are included in Tables 1, 2, and
3.  One tank representing each concentration in each diluter system was sampled
18 times during this 30 day study, except those tanks in which all fish died
before the end of the test.  On 11 and 12 of these sampling days, the
appropriate volume of Lake Superior water from the respective control tanks was
spiked to a concentration of 10 yg/liter of each chemical in acetone and the
sample was extracted and analyzed to determine the recovery of the extraction
procedure.  The recovery of hexachlorocyclopentadiene from 12 spiked samples
was 93.7 + 6.6%, of hexachloronorbomadiene from 11 spiked samples was
102 + 4%, and of heptachloronorbornene from 11 spiked samples was 101 + 3%.


BIOLOGICAL METHODS

     All three 30-day tests were conducted simultaneously beginning in April
and ending in May, 1977.  To begin each test, 25 one-day-old fathead minnow
larvae were randomly selected and distributed to each duplicate exposure
chamber.  All fish were fed brine shrimp nauplii 3 to 4 times a day.  Mortalities
were recorded after the fourth day and then once a week for the remainder of
the test.  Death was defined as complete immobilization and failureof the animals
to respond to probing.

     After the 30 day period all surviving fish were killed in ice water and
immediately measured for total length, blotted and weighed.  Whole fish were
then frozen in stainless steel weighing dishes for residue analysis.

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              TABLE  1.   SURVIVAL AND GROWTH OF FATHEAD MINNOWS EXPOSED TO VARIOUS CONCENTRATIONS OF
              HEXACHLOROCYCLOPENTADIENE ("HEX").   ASTERISK (*) DENOTES VALUES SIGNIFICANTLY LESS
                            THAN CONTROLS (ANALYSIS OF VARIANCE, DUNNETT'S TEST,  P=0.05).
VO
          Item
                                                Measured concentration (yg/liter)
                  9.1a ± 1.8      7.3 ± 4.7    3.7 ± 1.2    1.7 ±0.78    0.78 ± 0.31   <0.04  (control)
                   ABb       ABABAB       AB       A        B
                                                  4-day
Survival (%)       4*0       64  * 76     100   88     100   96       96    96      100      96
     Survival  (%)
     Length  (mm)
     Weight  (g)
                                                  30-day
                       *  0       60  * 72      96   84     100   92
                                 25.6 ± 2.9   24.6 ± 2.9   24.7 ± 2.3
                                 0.13 ± 0.04  0.11 ± 0.04  0.11 ± 0.03
 92    96
25.1 ± 2.3
0.12 ± 0.03
92      96
24.8 ± 2.5
0.12 ± 0.04
      Mean  ±  S.D.  of  duplicate  chambers.
      Duplicate  chamber.

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        TABLE 2.  SURVIVAL AND GROWTH OF FATHEAD MINNO'WS EXPOSED TO VARIOUS CONCENTRATIONS OF




         HEXACHLORONORBORNADIENE ("X").  ASTERISK (*) DENOTES VALUES SIGNIFICANTLY LESS THAN




                      CONTROLS (ANALYSIS OF VARIANCE, DUNNETT'S TEST, P=0.05).

Item

Survival (%)

Survival (%)
Length (mm)
Weight (g)
Measured
226a ± 26.3 122 ± 8.8 56.9
A B b A B A

28 * 48 84 * 72 96

0*0 72 * 60 96
19. 0 ± 2.3* 24.5
0.06 ± 0.02 0.11
concentration
± 10.2 38.4 ±
B A
4-day
96 96
30-day
96 92
± 1.6* 24.6 ±
± 0.03* 0.11 ±
(yg/liter)
3.1 20.0 ± 3.9
BAB

96 100 100

92 100 100
2.3* 25.0 ± 2.5
0.03 0.12 ± 0.03

<0.04 (control)
A B

100 100

96 92
25.9 ± 1.7
0.13 ± 0.03
Mean ± S.D. of duplicate chambers.



Duplicate chamber.

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         TABLE 3.  SURVIVAL AND GROWTH OF FATHEAD MINNOWS  EXPOSED  TO VARIOUS CONCENTRATIONS OF




          HEPTACHLORONORBORNENE ("Y").  ASTERISK (*) DENOTES VALUES SIGNIFICANTLY LESS THAN




                         CONTROLS  (ANALYSIS OF VARIANCE, DUNNETT'S TEST, P=>0.05).

Item

Survival (%)

Survival (%)
Length (mm)
Weight (g)
Measured concentration (yg/liter)
180. 3a + 14.8 164.9 ± 36.6 83.5 ± 7.1 40.0 ± 10.8 25.9 ± 3.4 <0.04 (control)
A Bb A BABABABA B
4-day
0*0 0*0 44 * 76 100 76 84 96 100 100
30-day
0*0 0*0 8 * 36 92 76 84 96 96 96
19.2 ± 3.3* 24.2 ± 2.2* 24.7 ± 2.8 25.4 ± 1.9
	 0.07 ± 0.03 0.11 ± 0.03 0.12 ± 0.03 0.12 ± 0.04
Mean ± S.D. of duplicate chambers.




Duplicate chamber.

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        ANALYSIS

     Whole fish were analyzed on a wet weight basis using the methods described
fry ffeith and Lee (1971).  Composite samples of all surviving fish in each
ifttyfticete tank were homogenized with anhydrous Waj»S
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                                SECTION 5

                                 RESULTS


HEXACBLOROCYCLOPENTADIENE ("hex")

Toxicity

     Survival of fathead minnow larvae was significantly decreased at 7.3
pg/liter and above after 4 days of exposure (Table 1).  A concentration of
9.1 yg/liter killed all but one fish after 4 days and all fish by 30 days.
Growth of fish surviving at concentrations of 7.3 yg/liter and below was not
significantly decreased from that in the controls (Table 1).

     The toxicity curve relating median lethal concentration (LC50) for "hex"
to exposure time is illustrated in Figure 2.


HEXACHLORONORBORNADIENE ("X")

Toxicity

     Concentrations of 122 and 226 tig/liter of "X" caused significant decreases
in survival of fathead minnow larvae after 4 days of exposure (Table 2).  By
the end of the test (30 days) all fish were dead at 226 yg/liter and the mean
survival at 122 pg/liter was 66%.  Significant decreases in survival did not
occur in concentrations lower than 122 yg/liter.  Growth of 30 day-old larvae,
however, was significantly decreased at concentrations of 38.4 yg/liter and above.

     The toxicity curve relating LC50 for "X" to exposure time is included in
Figure 2.

Accumulation

     The concentration of "X" accumulated by fathead minnows was directly
proportional to the mean exposure concentration up to a concentration of 38.4
yg/liter which decreased the growth of the fish.  As illustrated in Figure 3,
residues in 30 day-old fish exposed to 20 yg/liter contained an average of
129 yg/g which resulted in a bioconcentration factor of 6450.  A similar
bioconcentration factor of 6350 was obtained when fish were exposed to 38.4
pg/liter.  However, the bioconcentration factor at 56.9 yg/liter decreased to
4500, and further decreased to 4000 at 122 yg/liter.  Consequently, the
average bioconcentration factor for hexachloronorbornadiene in fish exposed to
concentrations less than 38.4 yg/liter was approximately 6400.


                                      13

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       300
       200
        100
         50
     Q
         IO
                                         10
2O
3O
                       EXPOSURE  TIME  (days)
Figure 2.  Relationship between LC50  (log scale) of hexachlorocyclopentadiene
          ("hex"), hexachloronorbornadiene ("X"), and heptachloronorbornene
          ("Y") to exposure time (log scale)  for fathead minnows.  Symbol •
          indicate mean value of "hex", • of  "X", and o of "Y".  Bars indicate
          95% confidence limits.
                                   14

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    lOOOr
                 EXPOSURE  CONCENTRATION  (jig/1)
Figure 3.  Residue accumulation (log scale) of "X" (•! and "Y" (pi measured
          in fathead minnows exposed for 30 -days.  Symbols and bars indicate
          the mean of duplicate pooled samples and S.D., respectively.
          Symbol with no bar indicates one pooled sample.
                                  15

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HEPTACHLORQNORBORNENE ("Y")

Toxicity

     Survival of fathead minnow larvae exposed to "Y" was significantly
decreased at 83.5 yg/liter and above after 4 days.  Higher concentrations of
164.9 and 180.3 yg/liter, killed all the fish within this period.  Additional
mortality occurred at 83.5 yg/liter after 30 days resulting in 22% survival.
Decreases in survival were not observed at the two lower concentrations of
40 and 25.9 yg/liter.  Lengths of fish, however, were significantly reduced
at 40 yg/liter and above after 30 days of exposure.

     The toxicity curve relating LC50 for "Y" to exposure time is included in
Figure 2.

Accumulation

     The concentration "Y" accumulated by fathead minnows was directly
proportional to the mean exposure concentration up to the "effect" concentration
of 40 yg/liter (Figure 3).  Fish exposed to 25.9 yg/liter "Y" accumulated an
average of 296 yg/g which resulted in a bioconcentration factor of 11,400,
Fish exposed to 40.0 yg/liter contained residues of 438 yg/g, which resulted
in a bioconcentration factor of approximately 11,000.  However, at 83.5 yg/liter,
588 yg/g were accumulated and the bioconcentration factor was reduced to 7000.
Consequently, the average bioconcentration factor for fish exposed to "Y" at
less than 40 yg/liter was 11,200.
                                      16

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                                  SECTION 6

                                 DISCUSSION


     Hexachlorocyclopentadiene (."hex") was more toxic to fathead minnows than
hexachloronorbornadiene ("X") or heptachloronorbornene ("Y").   A concentration
of "hex" causing adverse effects was approximately 5 times lower than concen-
trations of "X" and "Y" causing adverse effects to fathead minnows after the
same time period.  Hexachloronorbornadiene and heptachloronorbornene
significantly decreased growth at approximately the same concentrations.
Concentrations that decreased growth were 2 to 3 times lower than those
affecting survival.  This effect was different from that caused by "hex" since
this compound caused significant decreases in survival but not in growth.

     Comparison of the results of this test to earlier studies show that all
three chemical intermediates were more toxic to fathead minnows in this study
than to this same species and others exposed to these compounds for similar
time periods.  The 96-hr LC50 value of "hex" reported for fathead minnows in
this test was 8 times lower than the value reported for this species by the
U.S. Department of Health, Education and Welfare (1956).  The 96-hr LC50
values of "hex" in static bioassays reported for bluegills and bass (Davis and
Hardcastle, 1959) were approximately 2800 to 3600 times higher than 96-hr
values reported in this test.  Mount and Futnicki (1966) indicated that com-
pounds of "X" and "Y" would be 1,000 to 10,000 times less toxic than endrin
to guppies.  An earlier study by Mount (1962) showed that 0.4 to 0.5 yg/liter
of endrin caused mortality to guppies and bluntnose minnows and that little
mortality was due to endrin at 0.25 yg/liter.  These results indicate that "X"
and "Y" would be toxic to guppies at concentrations of 500 yg/liter and above
and that little effect would occur at concentrations below this.  However, in
the present test, approximately 40 yg/liter of "X" and "Y" caused significant
reductions in growth and 122 and 83.5 yg/liter, respectively,  caused
significant decreases in survival of fathead minnows.  The lower values
obtained in this test for all three compounds are probably due to the
utilization of intermittent-flow exposure systems and/or the use of the most
sensitive life stages of development for testing (Mount, 1962; McKim, 1977).

     The toxicity curve for hexachlorocyclopentadiene showed that a median
lethal threshold (the concentration at which acute toxicity of 50% of the
test animal ceases) was attained within 4 days.  The presence of a threshold
level for this exposure time would indicate that this compound was non-cumulative.
Toxicity curves for hexachloronorbornadiene and heptachloronorbornene showed
that these compounds may have had a cumulative action.  This is also
suggested because adverse effects on growth were observed at concentrations
much lower than those which decreased survival and by their high bioaccumulation
in whole body tissue.

                                      17

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     The accumulation of hexachloronorbornadiene and heptachloronorbornene in
fathead minnows was substantial at low exposure concentrations after 30 days.
The ability of these compounds to accumulate in fish is similar to that of the
persistent organochlorine insecticides including endrin, one of the most toxic
of all economic poisons to fish (Grant, 1976).  Their accumulation in fathead
minnows indicate both a real and potential hazard to higher food chain organisms.
Both "X" and "Y" have been found in edible fish such as catfish, carp, and
others (U.S. Food and Drug Administration, 1976).

     Residue concentrations of "hex" have not been found in edible fish and
its accumulation in fathead minnows was not demonstratable in this test because
of losses by vaporization during extraction.  Additional studies are needed
to determine the bioconcentration factor of "hex" since it is found in water
bodies together with sewage water from manufacturers of poisonous chemicals
and plastics (Naishstein and Lisovskaya, 1965).

     No information was found in the literature on the toxicity of hexachloro-
norbornadiene and heptachloronorbornene to mammals or humans.  Studies by
Ingle (1953), Treon et jil. (1955), and Hooker Chemicals and Plastics Corpora-
tion (1969), however, have shown that hexachlorocyclopentadiene is toxic to
mammals (guinea pigs, rats, mice and rabbits) via inhalation, ingestion or
dermal exposure.  Other effects caused by "hex" on mammals include degenerative
changes in several body organs, pulmonary edema, bronchitis, pneumonia, tremors,
irritation of mucous and respiratory membranes, increased breathing and others.
All three studies indicated that this compound can cause noxious effects to
humans such as skin burns and discomfort, eye irritation and headaches.
                                      18

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                                 REFERENCES


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Barthel, W, F., D. A. Parsons, L. L. McDowell, and E. H. Grissinger.  Surface
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Blau, 6. E., W. B. Neely, and D. R. Branson.  Ecokinetics: A study of the Fate
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Brooks, G. T.  Chlorinated Insecticides.  Vol. I.  Technology and Application.
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Brungs, W. A., and D. I. Mount.  Lethal Endrin Concentration in the Blood of
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Cardwell, R. D., D. G. Forman, T. R. Payne, and D. J. Wilbur.  Acute and
     Chronic Toxicity of Chlordane to Fish and Invertebrates.  EPA-600/3-77-019.
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Cole, E. J.  Treatment of Sewage with Hexachlorocyclopentadiene.  Appl. Micro-
     biol.  2:198-199.  1954.

Davis, J. T., and W. S. Hardcastle.  Biological Assay of Herbicides for Fish
     Toxieity,  Weeds, 7:397-404.  1959.

Defoe, D. L.  Multichannel Toxicant Injection System for Flow-Through Bioassays.
     J. Fish. Res. Board Can. 32:544-546.  1975.

Eaton, J. G., J. M. McKim, and G. W. Holcombe.  Metal Toxicity to Embryos and
     Larvae of Seven Freshwater Fish Species - I Cadmium.  Bull. Environ.
     Contam. Toxicol.  In Press, 1977.
                                      19

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Grant, B. F.  Endrin Toxicity and Distribution in Freshwater.   A Review.
     Bull. Environ. Contam. Toxicol. 15(3):283-290.  1976.

Hamilton, M. A., R. C. Russo, and R. V. Thurston.  The Trimmed Spearman-Karber
     Method for Estimating Median Lethal Concentrations in Toxicity Bioassaya.
     Environ. Sci. and Technol.  11(3):714-719.  1977.

Hansen, D. J., P. R. Parrish, J. I. Lowe, A. J. Wilson Jr., and P. D. Wilson.
     Chronic Toxicity, Uptake and Retention of AroclorR 1254 in Two Estuarine
     Fishes.  Bull. Environ. Contam. Toxicol. 6(2):113-119.  1971.

Henderson, C., Q. H. Pickering, and C. M. Tarzwell.  Relative Toxicity of Ten
     Chlorinated Hydrocarbon Insecticides to Four Species of Fish.  Trans.
     Am. Fish. Soc.  88:23-32.  1959.

Hooker Chemicals and Plastics Corp., Industrial Chemicals Division.
     Hexachlorocyclopentadiene.  Data Sheet No. 815A.  1969.

Ingle, L.  Toxicity of Chlordane Vapors.  Sci. 118:213-214.  1953.

Johnson, H. E.  The Effects of Endrin on the Reproduction of a Freshwater
     Fish (Oryzias latipes).  Ph.D. Thesis, University of Washington.  136 p.
     1967.

Lu, P. Y., R. L. Metcalf, A. S. Hirwe, and J. W. Williams.   Evaluation of
     Environmental Distribution and Fate of Hexachlorocyclopentadiene, Chlordane,
     Heptachlor, and Heptachlor Epoxide in a Laboratory Model Ecosystem.
     J. Agric. Food Chem. 23(5):967-973.  1975.

Macek, K. J., C. Hutchinson, and 0. B. Cope.  The Effects of Temperature on the
     Susceptibility of Bluegills and Rainbow Trout to Selected Pesticides.  Bull.
     Environ. Contam. Toxicol.  4:174.  1969.

McKim, J. M.  Evaluation of Tests With Early Life Stages of Fish for Predicting
     Long-Term Toxicity.  J. Fish. Res. Board Can.  34(8):1148-1154.  1977.

McKim, J. M., J. W. Arthur, and T. W. Thorslund.  Toxicity of a Linear Alkylate
     Sulfonate Detergent to Larvae of Four Species of Freshwater Fish.  Bull.
     Environ. Contam. Toxicol. 14:1-7.  1975.

McKim, J. M., J. G. Eaton, and G. W. Holcombe.  Metal Toxicity to Embryos and
     Larvae - Early Juveniles of Eight Species of Freshwater Fish  II.  Copper.
     Bull. Environ. Contam. Toxicol.  In Press, 1977.

Mount, D. I.  Chronic Effects of Endrin on Bluntnose Minnows and Guppies.  U.S.
     Fish & Wildl. Serv. Res. Rep. 58.  1962.

Mount, D. I., and G. J. Putnicki.  Summary Report of the 1963 Mississippi Fish
     Kill.  Trans. 31st No. Amer. Wildl. and Nat. Res. Conf. p. 177.  1966.
                                      20

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 Mount,  D.  I.,  L. W. Vigor, and M. L. Schafer.  Endrin:  Use of Concentration
      in Blood  to Diagnose Acute Toxicity to Fish.  Sci. 152:1388-1390.   1966.

 Naishstein,  S. Ya., and E. V. Lisovskaya.  Maximum Permissible Concentration of
      Hexachlorocyclopentadiene in Water Bodies.  Gig. Sanit., 30:177-181.   1965.

 National Academy of Sciences and National Academy of Engineering.  Water
      Quality Criteria  1972,  A Report of the Committee on Water Quality  Criteria
      Environmental Studies Board, Washington, D.C.  594 p.  1973.

 Pickering, Q.  H., and  M, H. Cast.  Acute and Chronic Toxicity of Cadmium to
      the Fathead Minnow, Pimephales promelas.  J. Fish. Res. Board Can.
      29:1099-1106.  1972,

 Pickering, Q.  H., and  T. 0. Thatcher.  The Chronic Toxicity of Linear Alkylate
      Sulfonate (LAS) to Pimephales promelas Rafinesque.  J, Water Poll.  Cont.
      Fed.  42:243-254.  1970.

 Reinert, R.  E. The Accumulation of Dieldrin in an Alga (Scenedesmus obliguus),
      Daphnia (Daphnja  magna), Guppy (Lebistes reticulatus) Food Chain.   Ph.D.
      Thesis, University of Michigan.  76 p.  1967.

 Sprague, J.  B. Measurements of Pollutant Toxicity to Fish.  1.  Bioassay
      Methods for Acute Toxicity.  Water Res., 3:793-821.  1969.

 Steel,  R.  G. D., and J, H. Torrie.  Principles and Procedures of Statistics
      with  Special Reference to the Biological Sciences.  McGraw-Hill, Inc.
      New York, N.Y.  481 p.  1960.

 Treon,  C,, F.  Cleveland, and J, Cappel.  The Toxicity of Hexachlorocyclopentadiene.
      Arch. Indust. Health, ll;459-472,  1955.

 U.S.  Department of Health, Education, and Welfare.  In a Report by Equitable
      Environmental Health for Hooker Chemical Company, Niagara Falls, New
      York.   1956.

 U.S.  Environmental Protection Agency.  Early Warning Report on Hexachlorocyclo-
      pentadiene and its Derivatives (draft).  Office of Toxic Substances,
      Washington, D.C.  20460.  1977.

 U.S.  Food  and  Drug Administration.  On Findings of Residues of Three Chlorinated
      Chemicals in Edible Fish, 1,2,3,4,7,7-hexachloronorbornadiene, 1,2,3,4,5,
      7,7-heptacbloronorbornene, and 5,6«-epoxy>-1,2,3,4,7,7^hexachloronorborn-
      2-ene in  1972-1974.   (Personal Communication letter)  1976.

Veith, G. D., and G. F. Lee,  PCB's in Fish from the Milwaukee Region.  Proc.
      14th  Conf. Great  Lakes Res. 157<-169.  Internat. Assoc. Great Lakes  Res.
      1971.
                                       21

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                                   TECHNICAL REPORT DATA
                            (Please read Instructions on the reverse before completing)
,1. REPORT NO.
! fl»ft*"600/3-77-099
                           3. RECIPIENT'S ACCESSION NO.
4i "Plflie-AtilO SUBTITLE
  & R&pld  Assessment of the Toxicity of  Three Chlorinate<
    CT^lodiene Insecticide Intermediates  to Fathead
    W&swows
                           5. REPORT DATE
                                August 1977  issuing date
                           6. PERFORMING ORGANIZATION CODE
          L.  Spehar, Oilman D. Veith, David L.  DeFoe,
       Barbara A.  Bergstedt
                                                           8. PERFORMING ORGANIZATION REPORT NO.
            ORGANIZATION NAME AND ADDRESS
  ffittXironmental Research Laboratory - Duluth, MN
  (Office of Research and Development
  $.S.  Environmental Protection Agency
  Duluth,  Minnesota 55804
                           10. PROGRAM ELEMENT NO.

                              1BA608  	
                           11. CONTRACT/GRANT NO.

                              In-house
 12. SPONSORING AGENCY NAME AND ADDRESS
           SAME AS ABOVE
                                                           13. TYPE OF REPORT AND PERIOD COVERED
                                                              Final	
                           14. SPONSORING AGENCY CODE
                              EPA/600/03
 15. SUPPLEMENTARY NOTES
 16. ABSTRACT
       A rapid assessment study to determine the toxicity and bioaccumulation of three
  chlorinated cyclodiene insecticide  intermediates; hexachlorocyclopentadiene,
  hexachloronorbornadiene, and heptachloronorbornene to fathead minnow larvae and early
  juveniles was conducted for 30 days under flow-through conditions.
        A concentration of 7.3 yg/liter of hexachlorocyclopentadiene caused  significant
  decreases in survival after 4 days.   Growth of fish exposed for 30 days was not
  significantly decreased at any of the concentrations tested.  The highest concen-
  tration of hexachlorocyclopentadiene having no adverse effect was 3.7 yg/liter.
        Concentrations of 122 and 226  yg/liter of hexachloronorbornadiene caused
  significant decreases in survival after 4 days.  Growth of 30 day-old larvae  was
  significantly decreased at 38.4 yg/liter and was the most sensitive indicator of
  toxicity.  The highest concentration having no adverse effect was 20.0 yg/liter.  The
  average bioconcentration factor for fish exposed to less than 38.4 yg/liter of this
  compound was 6400.
        Survival of fathead minnows exposed to heptachloronorbornene was significantly
  decreased at 83.5 yg/liter after 4  days.  Growth was significantly reduced at 40
  yg/liter after 30 days and was the  most sensitive indicator of toxicity.   The highest
  concentration having no adverse effect was 25.9 yg/liter.  The average bioconcen-
  tration factor for fish exposed to  less than 40 us/liter of this compound in  water was
,7.11,200.
KEY WORDS AND DOCUMENT ANALYSIS
                  DESCRIPTORS
                                              b.lDENTIFIERS/OPEN ENDED TERMS
                                         c. COSATI Field/Group
  Bioassay
  Freshwater
    fishes
  Residues
  Survival
  Growth
  Minnows
  Toxicity
Fathead minnows
Acute toxicity tests
Chronic toxicity  tests
Early developmental
  stages
Bioaccumulation
Organochlorine
  insecticides	
                                                                           06  F
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