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CAUFDRNIA
FISH- GAME

"CONSERVATION OF WILDLIFE THROUGH EDUCATION"



VOLUME 71



JULY 1985



NUMBER 3









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California Fish and Game is a journal devoted to the conservation of wild-
life. If its contents are reproduced elsev/here, the authors and the California
Department of Fish and Game would appreciate being acknowledged.

Subscriptions may be obtained at the rate of $5 per year by placing an
order with the California Department of Fish and Game, 1416 Ninth Street,
Sacramento, California 95814. Money orders and checks should be made out
to California Department of Fish and Game. Inquiries regarding paid sub-
scriptions should be directed to the Editor.

Complimentary subscriptions are granted, on a limited basis, to libraries,
scientific and educational institutions, conservation agencies, and on exchange.
Complimentary subscriptions must be renewed annually by returning the post-
card enclosed with each October issue.



Please direct correspondence to:

Perry L. Herrgesell, Ph.D., Editor
California Fish and Game
1416 Ninth Street
Sacramento, California 95814



u






D



VOLUME 71



JULY 1985



NUMBER 3




Published Quarterly by

STATE OF CALIFORNIA

THE RESOURCES AGENCY

DEPARTMENT OF FISH AND GAME

—LDA—



130 CALIFORNIA FISH AND CAME



STATE OF CALIFORNIA
GEORGE DEUKMEJIAN, Governor



THE RESOURCES AGENCY
GORDON VAN VLECK, Secretary for Resources



FISH AND GAME COMMISSION

WILLIAM A. BURKE, Ed.D., President
Brentwood
BRIAN J. KAHN, Vice President ABEL C. GALLETTI, Member

Santa Rosa Los Angeles

ROBERT BRYANT, /Member ALBERT C. TAUCHER, Member

Yuba City Long Beach



DEPARTMENT OF FISH AND GAME

JACK C. PARNELL, Director

1416 9th Street

Sacramento 95814



CALIFORNIA FISH AND GAME

Editorial Staff

Editorial staff for this issue consisted of the following:

Wildlife William E. Grenfell, Jr.

Marine Resources Robert N. Lea, Ph.D.

Anadromous Fish Donald Stevens

Editor-in-Chief Perry L. Herrgesell, Ph.D.



131
CONTENTS

Page
Acute Toxicity of Seven Alicyclic Hexanes To Striped Bass,
Morone saxatilis, and Bay Shrimp, Crangon franciscorum, in

Seawater Pete E. Benville, Jr.,

Jeannette A. Whipple and Maxwell B. Eldridge 132
An Analysis of Canvasbacks Banded in

California Warren C. Rienecker 141

The Survival and Mortality of Seeded and Native Red Aba-
lones, Haliotis rufescens, on the Palos Verdes

Peninsula Mia J. Tegner and Robert A. Butler 150

Intermarsh Movements By Light-Footed Clapper Rails Indicat-
ed In Part Through Regular Censusing Richard Zembal,

jack M. Fancher, Christopher S. Nordby 164
Bird Diets and Prey Availability in The Western Sierra Nevada,

California Donald L. Dahlsten,

Michael L. Morrison, David L. Rowney,

Marilyn Wilson and Yosef Cohen 172
Determining The Sex of Sea Otters From Skulls Aryan I. Roest 179

NOTES

A Technique to Secure Small Mammal Livetraps Against Dis-
turbance Donald R. Warner and David L. Chesemore 184

Northward Range Extension For the Striped Marlin

Keven Hill and David R. Haight 185

Occurrence of a Juvenile California Lizardfish, Synodus

lucioceps, in Washington Waters

Gary P. Gonyea and Steve F. Burton 188

The Scalloped Hammerhead, Sphyrna lewini, In Coastal
Southern California Waters: Three Records Including the
First Reported Juvenile Jeffrey A. Seigel 189

Book Reviews 191



132 CALIFORNIA FISH AND GAME

Calif. Fish and Came 7^(3): ^32-^ 40 1985

ACUTE TOXICITY OF SEVEN ALICYCLIC HEXANES TO

STRIPED BASS, MORON E SAXATI US, AND BAY SHRIMP,

CRANGON FRANCISCORUM, IN SEAWATER ^

PETE E. BENVILLE, JR, JEANNETTE A. WHIPPLE, AND MAXWELL B. ELDRIDGE

National Marine Fisheries Service

Southwest Fisheries Center

Tiburon Laboratory

3150 Paradise Drive

Tiburon, California 94920

Field monitoring studies have shown that many striped bass, Morone saxatilis, in
California's Sacramento-San Joaquin Estuary are burdened with a wide variety of
pollutants including many types of petroleum hydrocarbons. Alicyclic hydrocarbons
are among these pollutants but there was no information on their toxicity to striped
bass. Our studies were concerned with the acute toxicities of the simplest alicyclics
in comparison to their counterparts in the aromatic series. The alicyclic compounds
were cyclohexane, methylcyclohexane, ethylcyclohexane and four dimethylcy-
clohexanes (1,1; 1,2; 1,3; and 1,4). Acute toxicities after 24 and 96 h exposures to
seven alicyclic hexanes were determined for striped bass and one of their major food
organisms, the bay shrimp, Crangon franciscorum. The 96 h LC50S for striped bass and
bay shrimp ranged from 3.2 to 9.3/j.I/I and from 1.0 to 6.2 ;xl/l, respectively. Slight
differences were noted between the 24 and 96 h LCso values in all but two bioassays.
Solubilities of these alicyclics in seawater and freshwater were determined since
information in the literature was limited. Solubility was inversely related to the
complexity of the alicyclic structure and ranged from 5.3 to 62 /ml/l in distilled water
and from 4.6 to 44 jul/l in seawater. Alicyclics were generally more soluble in distilled
water than in seawater. Tissue analyses showed greater bioaccumulation in striped
bass, which have more lipid than bay shrimp. Striped bass had up to 260 /xl/kg (wet
weight) of an alicyclic hexane after exposure to water concentrations ranging from
0.32 to 12 /Lil/I. Bay shrimp residues were as much as 110 jal/kg of an alicyclic hexane.

INTRODUCTION

Alicyclic hexanes were recently found in liver and ovary tissues (0.02 to 16
jal/kg wet weight) of striped bass, Morone saxatilis, taken from the Sacramento-
San Joaquin Estuary (Whipple, Eldridgeand Benville 1981 ). Along with monocy-
clic aromatic hydrocarbons, the alicyclics were associated with poor physiologi-
cal conditions (egg resorption and lesions with cestode larvae) leading to
possible organ dysfunctions. Because little information exists on the toxic effects
of these petroleum compounds, we conducted a series of experiments to deter-
mine the toxicological consequences of alicyclic hexanes to striped bass and bay
shrimp, Crangon franciscorum.

Alicyclic hexanes are six-carbon ring structures in the cyclic aliphatic hydro-
carbon class (cycloalkanes) of organic compounds which are relatively nonpo-
lar and have low solubility in water (Morrison and Boyd 1966). Seven low
molecular weight alicyclic hexanes found in the tissues of striped bass collected
from the San Francisco Bay were selected for acute toxicity tests. These alicy-
clics were: cyclohexane, methylcyclohexane, four dimethylated forms 1,1-; cis^
and trans-1,2 — ; cls-1,3 — ; and cis- and trans -1 ,4-dimethylcyclohexane
(DMCH), and ethylcyclohexane (ECH) (Figure 1).



Accepted for publication August 1984.



ALICYCLIC HEXANE TOXICITY



133





CH2CH3




Cyclohexane



Methylcyclohexane



Ethylcyclohexane








1,1-Dimethylcyclohexane



1,2 (ortho)-Dimethylcyclohexane
trans > cis
(stability)





1,3 (meto) -Dimethylcyclohexane
cis > trans



1,4 (para)-Dimethylcyclohexane
trans > cis



FIGURE 1. Structural formulas of seven alicyclic hexanes.



While some alicyclics entering the aquatic environment are of biogenic origin
(e.g. plant metabolites), most alicyclics are from anthropogenic sources such as
oil spills and waste discharges.

MATERIALS AND METHODS

Solubility Determinations

The lack of published solubility values for most of the seven alicyclics neces-
sitated the determination of their solubility in distilled water and seawater before
we could conduct the toxicity experiments.

To determine the solubilities of the seven alicyclics, saturated solutions were
prepared by shaking 0.22 ml of each alicyclic with 220 ml water in a 250 ml
separatory funnel for 1 min and letting the mixture settle for 24 h at 20° C. Two
100 ml portions of the saturated water extracts were drained into 125 ml separa-
tory funnels; each portion was extracted in succession with three 10 ml aliquots
of TF-Freon (trichlorotrifluoroethane) (Reference to trade names does not im-
ply endorsement by the National Marine Fisheries Service, NOAA.). Samples
were processed as described under Analytical Procedure, below.



134 CALIFORNIA FISH AND GAME

Bioassay Procedure

Juvenile striped bass (mean weight = 8.5 g, mean total length = 9.2 cm) were
obtained from freshwater at the U.S. Bureau of Reclamation fish screening
facility at Tracy, California, and acclimated to seawater at our laboratory in
Tiburon, California. Bay shrimp (mean weight = 1.7 g, mean length = 6.4 cm),
were acquired from a local bait dealer in San Rafael, California. Mortality from
transportation and salinity change during the first 24 h was 20% for striped bass
and less than 1% for bay shrimp. All animals were held in flow-through 200 I
tanks for 2 wk before toxicity testing (Korn 1975). Mortality during this period
was less than 1% for both fish and shrimp. Salinity and temperature of the
seawater increased during the holding period from 27 to 32 °/oo and 15 to 20°C,
respectively.

Static bioassays were conducted with each alicyclic using five oval fiberglass
aquaria with dimensions of 1 10 cm length X 50 cm width X 40 cm height. Each
aquarium was filled with 180 I of filtered seawater. Five alicyclic aliquots ranging
in geometric progressions from 1 to 16 ml were mixed with seawater to achieve
the necessary nominal concentrations. Test-tank solutions were prepared by
adding the alicyclics slowly (8 ml/min) into a mechanically-generated seawater
vortex. Immediately after the appropriate amount of alicyclic was introduced
into each aquarium, ten animals of each species were placed in each aquarium.
No aeration was used during the testing period. The bay shrimp were separated
from the fish by placing them in a 30 cm length X 16 cm width X 14 cm height >
basket. Two 10 ml seawater samples were pipetted at mid-depth from each
aquaria before and after introducing the animals to determine the alicyclic
concentrations. These samples were immediately extracted with 10 ml of TF-
Freon and analyzed as described under Analytical Procedure. Each succeeding
day a 100 ml water sample was taken, extracted and analyzed. Mortalities were
noted daily. Bioassay procedures followed were from Standard Methods (Con-
nors, Jenkins and Greenberg 1981 ). LC50S and confidence limits were calculated
by the Litchfield and Wilcoxon (1949) method.

All fish and shrimp were analyzed for alicyclic residues at the end of the 96
h tests. Animals were frozen using dry ice and ground into a powder (Benville
and Tindle 1970). A composite of 10 g homogenized tissue was then processed
for alicyclic concentrations (Nunes and Benville 1979).

Analytical Procedure
The alicyclics in each Freon extract were separated and analyzed with a
Hewlett-Packard 5880 gas chromatograph (GO equipped with a dual flame
ionization detector. Standard solutions of each alicyclic hexane were made for
calibrating the GC. A combined standard was made from the seven alicyclics,
six monocyclic aromatics and nonane to determine the relative location of each
compound (Figure 2). The six aromatics were benzene, toluene, ethylbenzene
and three xylene isomers ( ortho -, rneta, and para-). All alicyclics were eluted
from the Bentone-34/SP-1200 column at 65°C within 8 min. After all the alicy-
clics were separated, the temperature was increased to 120° C to remove all the
aromatics. There were overlapping retention times between the DMCHs and
ethylcyclohexane (ECH) using the Bentone-34/SP-1200 column. However,
each bioassay involved only a single alicyclic and analytical interferences were
not encountered. Benzene was eluted within the alicyclic group but caused no



ALICYCLIC HEXANE TOXICITY 135

interference. Temperature programnning was started after 10 min. running tinne
to elute the ethylbenzene and xylene isomers within a reasonable time frame ( 1 5
min). The four dimethylated alicyclics and ethylcyclohexane had overlapping
retention times and emerged in the following three groups: 1,1-DMCH, cis-1,3-
DMCH and trans -1,4-DMCH; trans-1,2-DMCH and cis-1,4-DMCH; and cis-1,2-
DMCH and ECH. No trans-l,3-DMCH was available for standardization; conse-
quently its elution time was unknown. One unknown peak appeared at 2.653 min
which was an inherent characteristic of the TF-Freon solvent. The ratio of the
OS- and trans-isomers that appeared for 1,2-, 1,3- and 1-4-DMCH were 41/59,
100/0 and 25/75, respectively. Alicyclic data reported in ppm are in jml/l for
water sample and jitl/kg for tissue samples based on wet weight.

RESULTS

Solubilities
All seven alicyclics had solubilities in the low ppm range (Table 1). The
number of alkyl groups on the cyclohexane compounds is in inverse proportion
to its water solubility, with cyclohexane the most soluble and dimethyl and ethyl
alicyclics the least soluble. In general, the position of the methyl groups appears
to affect the solubility. The further apart the two groups were from each other,
the less soluble was the DMCH. Solubilities also changed with salinity. Alicyclics,
except for ECH, were more soluble in distilled water than in seawater; ECH had
the same solubility in both distilled water and seawater. Solubility values ranged
from 5.3 to 62 ppm in distilled water and from 4.6 to 44 ppm in seawater. The
solubility of most of the alicyclics in seawater was lower by 24 to 29%; cis-1,3-
DMCH had only a 10% reduction and there was no change for ECH. Ratios of
the two optical isomers (cis- and trans-) in 1,2- and 1,4-DMCH compounds
were altered slightly favoring the cis- form after they were dissolved in water,
from 41/59 and 25/75 to 45/55 and 30/70 for distilled water and 44/56 and
28/72 for seawater, respectively.

Acute Toxicity and Tissue Residues

The alicyclics were more toxic to bay shrimp than to striped bass (Table 2).
Acute toxicities of the seven alicyclics ranged from 4.7 to 10.9 ppm for striped
bass and from 1 .5 to 6.5 ppm for bay shrimp within a 24 h period. The 96 h tests
showed slightly higher toxicities, although cyclohexane for striped bass and
1 ,3-DMCH for bay shrimp had similar acute toxicities for both exposure periods.
Mixtures of the cis- and trans -DMCH (1,2- and 1,4-) isomers were more toxic
to both striped bass and bay shrimp than the two pure DMCH's (1,1- and 1,3-).
Acute toxicity values (LCjoS) of ECH, 1,3-DMCH and 1,4-DMCH for striped
bass exceeded the solubility of the compound in seawater; for bay shrimp, only
the LC50 for ECH and 1,3-DMCH exceeded the seawater solubility.



136



CALIFORNIA FISH AND CAME




A Solvent (TF Freon)

B Cyclohexane

C Unknown

D Methylcyclohexane

E Benzene

F 1,1; cis-1.3, and trans 1,4- Dimethylcyclohexanes

G. trans -1,2 and cis 1,4 Dimethylcyclohexanes

H CIS 1,2 Dimethylcyclohexane & Ethylcyclohexane

Toluene
J Nonane
K Ethylbenzene
L. p-Xylene
M. m Xylene
N. o-Xylene



4 8 12

MINUTES

FIGURE 2. Chromatogram of nine alicyclics, six aromatics and nonane.

The striped bass and bay shrimp rapidly bioaccumulated the alicyclics many
times above the initial water dosage. Test concentrations of alicyclics in seawater
ranged from 0.32 to 11 ppm which resulted in uptakes by striped bass from
"nondetectable" levels to 260 ppm (wet weight) and by bay shrimp from 4.4
to 110 ppm (Table 3). Water insoluble alicyclics were accumulated to higher
levels by the organisms than were the more soluble ones.



ALICYCLIC HEXANE TOXICITY



137



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138 CALIFORNIA FISH AND CAME

TABLE 3. Resulting Concentrations of Alicyclic Hexanes in Tissues of Striped Bass and Bay
Shrimp from Test Containers.

Concentration Range of Alicyclics Ippm)
Water Striped Bay

Alicyclic Hexanes* (v/v)] bass (v/wj shrimp (v/w)

Cyclohexane 54-10 N.D.J- 48 4.4- 6.9

Methylcyclohexane 54- 7.3 N.D.j:-130 16 - 26

Ethylcyclohexane 1.5-11 5.8- 63 8.5- 66

1.1 Dimethylcyclohexane 1.5-8.7 23-170 9.1-110

1.2 Dimethylcyclohexane 32-7.9 1.1-260 24-47

1.3 Dimethylcyclohexane 1.6-12 6.5-160 7.0-100

1.4 Dimethylcyclohexane 1.2-7.1 28-46 12-36

* 1,2 and 1,4 dimethylcyclohexanes are mixtures of cis and trans isomers.

t V = Volume, w = Weight, Initial dosage

X N.D. = Non detectable below 0.7 )n.l/kg for tissue sample.

We noted that striped bass were more docile, easier to net and transfer after
the 96 h testing period than before the dosing began. Striped bass exposed to
the high dose of 1,3-DMCH (12 ppm) swam in tight clockwise circles instead
of swimming around the aquaria like the control fish when the aquaria were
disturbed. Some fish dosed with other alicyclics at lower concentrations would
do the same but not as long (only 10-15 s).

DISCUSSION

The acute toxicity (24 h bioassay) of the alicyclics to striped bass and bay
shrimp was in the low ppm range (1.5 to 10.9 jal/l) which is considered moder-
ately toxic to fish and invertebrates relative to other compounds (Benville and
Korn 1977). Extending the toxicity testing interval 3 more days resulted in
increases in the toxicity of all bioassays except for two tests (striped bass/
cyclohexane and bay shrimp/ 1,3 DMCH). The slight increase in toxicity was
probably due to the delayed effects of the alicyclics since alicyclics rapidly
escape from solution, resulting in alicyclic concentrations too low to cause acute
effects. Using a continuous flow method of dosing would probably show higher
toxicities (lower LCsqS). Static tests usually result in higher LC50 values (lower
toxicity) than continuous dosing because the concentration of the toxicant is
decreasing and not being replenished using the static method.

Three of the alicyclics ( ECH, 1 ,3 DMCH and 1 ,4 DMCH ) had solubility values
below their LC50 concentration values for striped bass (Figure 3). Researchers
usually use a solubilizing agent to disperse "insoluble" toxicants without know-
ing the effects of the solubilizers. Therefore, we did not use any dispersing agents
in this study.

Striped bass appeared to be more sensitive to alicyclics than other fish species
that have been tested. Pickering and Henderson (1966) reported 96 h TLms
(median tolerance limits) of cyclohexane for fathead minnows, Pimephales
promelas; bluegills, Lepomis macrochirus; goldfish, Carassius auratus; and gup-
pies, Lebistes reticulatus, of 42, 45, 55 and 75 jllI/I, respectively. These are 5 to
9 times higher than the toxic levels to striped bass. Jenkins, Klein and Cooper
(1977) found an LC50 of 84 jal/l for methylcyclohexane with golden shiners,
Notemigonus chrysoleucas, 14 times the level of toxicity for striped bass. Al-
though little data are available on the toxicity of higher homologs of cyclohexane



ALICYCLIC HEXANE TOXICITY



139



to fish, mammals show an increase in the narcotic action and toxicity when alkyl
groups are added to cyclohexane (von Oettingen 1942). We found that MCH,
1,1 DMCH, 1,2 DMCH and 1,4 DMCH were narcotic to striped bass. Perhaps
ECH and' 1,3 DMCH also would have been narcotic if their solubilities were
higher.



1.000,-



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A
A


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O


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Saawatar


V/M


SohjbWty




1 1




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^



ALICYCLIC HEXANES

FIGURE 3. Solubilities, acute toxicities and maximum tissue residues of seven alicyclic hexanes.



Alicyclics bioaccumulated in striped bass and bay shrimp by factors of 33x
and 13x, respectively. The greater accumulation in striped bass is due primarily
to their higher lipid content. Alicyclic residues might have been much higher,
as our research has indicated with monocyclic aromatic hydrocarbons (Whip-
ple et al. 1981), if the samples were taken at the optimum exposure time.
Aromatics accumulate rapidly in aquatic animals. Benzene (the simplest aro-
matic) accumulated in high concentrations in striped bass shortly after 40-min



140 CALIFORNIA FISH AND CAME

exposure (Whipple et al. 1981). A 1.5x to 119x increase above the ambient
water concentration of benzene was noted depending on the tissue analyzed.
Muscle had the lowest uptake and fat the highest uptake of the twelve analyzed
tissues. Other scientists have shown that fish can accumulate monocyclic aro-
matic hydrocarbons from chemical mixtures, e.g. crude oil (Roubal, Stranahan
and Malins 1978).

It has been suggested that cycloalkanes and other Water Soluble Fraction
compounds from petroleum and its products may be more toxic than aromatics
or that there is an additive effect with aromatics present (Caldwell, Caldarone
and Mallon 1 977 ) . Further research should be conducted to study the interaction
and combined effect of these two groups of cyclic compounds and to determine
if the additive effects are manifested at the population and community levels.

ACKNOWLEDGMENTS
We thank M. Jung and S. Korn for their comprehensive review of our manu-
script. R. Hamilton was very helpful in the technical part of this study and
developed many computer programs for this work for which we are grateful. A
special appreciation goes to R. Fisher and J. Greeley for editing and typing this
manuscript.

LITERATURE CITED

Benvllle, P. E., )r., and R. C. Tindle. 1970. Dry ice homogenization procedure for fish samples in pesticide residue

analysis. Agr. Food Chem., 18(5):948-949.


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