BIOLOGICAL MAGNIFICATION OF PHOTODIELDRIN

BY FOOD CHAIN ORGANISMS

H. M. KHAN and M. A. Q. KHAN
Department of Biological Sciences
University of Illinois at Chicago Circle
Chicago, Hlinois 60680

Species differences were seen among fresh-water invertebrates and fishes in the
absorption and subsequent retention of photodieldrin (a sunlight conversion product
of the insecticide, dieldrin). The cr~iyfish Cambarus and the clam Simpsoniconcha
showed extremely low levels of absorption and accumulation while the larvae of
the mosquito Aedes, the amphipod Gammarus, and the cladocerans Simocephalus,
and fresh-water flea Daphnia showed much higher levels of this insecticide. Maxi-
mum absorption occurred within 12 to 24 hours of exposure in only a few in-
vertebrates but in most fishes. Among fishes, five to six times higher levels were
seen during this period in guppy and goldfish than in minnow and bluegill. While
the livebearer, guppy, kept absorbing photodieldrin with time, other fishes showed
a slight decline in their tissue levels of this insecticide. The maximum biological
magnification ratios during peak periods of absorption were: 133 for bluegill, 150 for
minnow, 609 for goldfish, and 820 for guppy. Among microcrustacea the maximum
biological magnification ratios seen after four days of continuous exposure were
about 1000 for Simocephalus, 1200 for Garnmarus, and 63,000 for Daphnia. No
appreciable in vivo metabolism of photodieldrin was seen in fishes, minnow and
bluegill, and the decline in their body levels of photodieldrin is apparently not due
to detoxication of the latter.

The conversion of some of the commonly used chlorinated cyclodiene insecticides~,

aldrin, dieldrin, heptachlor, isodrin, and chlordene, by sunlight and ultraviolet light, to
their corresponding isomers photoatdrin (PA), photodieldrin (PD), photoheptachlor (PH),
photoisodrin (PI), and photochlordene (PC), respectively, affects their toxicity to
animals. The first three photoisomers generally become more toxic while photoisodrin
and photochlordene become less toxic than their respective parent compounds to
animals (Khan et al. 1973).

Since cyclodiene insecticides have been shown to accumulate in the body fat and
become concentrated through food chains (Woodwell et aL 1967), the fate and biological
concentration of their photoisomers in aquatic animals needs to be investigated.

Initial studies with photoaldrin, photodieldrin, and photoisodrin in houseflies,

mosquito larvae (Rosen et al. 1966; Khan et al. 1970), and rats (Klein et al. 1968)have
shown that the first two compounds are oxidatively dehydrochlorinated to a more toxic

1For structural formulae and nomenclature see Benson (1969).

Archives of Environmental Contamination 289

and Toxicology, Vol. 2, No. 4, 1974, © 1974
by Springer-Verlag New York Inc.
290 H.M. Khan and M. A. Q. Khan

metabolite, photodieldrin ketone (Khan et aL 1969), while photoisodrin is rapidly de-

toxified to hydrophilic metabolite(s) in houseflies (Khan et al. 1970).

We have investigated the biological magnification of photodieldrin by aquatic animals

as well as its metabolism by certain fishes. Results of these investigations are reported
here.

Materials
Algae. The culture of the algae Ankistrodesrnus spiralis was maintained in the
laboratory.

Animals. Fresh-water invertebrates: Larvae of the Mosquito Aedes aegypti (Insecta,

Diptera), a susceptible strain from Wisconsin Alumni Research Foundation, Madison,
Wisconsin, were used. Other invertebrates, purchased from the Coe-Palm Biological
Supplies, Chicago, were Daphnia, Simocephalus vetulus (Cladocera); Gammarus (Amphi-
pod); Crayfish Carnbarus; Glass Shrimp, Palaernonetes (Decapoda); and the Clam,
Simpsoniconcha ambigua (MoUusca Pelecypoda). Cultures of mosquitoes and micro-
crustaceans were maintained in this laboratory; other invertebrates were acclimated in
fresh-water at room temperature for seven to ten days before testing.

The following vertebrates were used in these studies: Fresh-water fishes: bluegill,
Lepomis machrochirus; minnow, Lebistes reticulata; goldfish, Carassius auratus; and
guppy, Gambia affinis. Two-months-old fry of bass and bluegill were obtained from the
Illinois Hatchery, Spring Grove, Illinois. Other fishes were purchased from Auburndale
Goldfish Co., Chicago. All the fishes were acclimated at room temperature for seven to
ten days before testing.

Chemicals. Dieldrin was obtained from Shell Chemical Company, New York, as
analytical standard (99% + pure). J4C-labelled dieldrin (specific activity, 61 mCi/mM)
was purchased from Amersham/Searle Co. Radioactive pbotodieldrin (99% + pure;
specific activity, 4.3 mCi/mM) was produced from radioactive dieldrin by exposing the
latter to UV-light and purifying photodieldrin by recrystallization (Rosen and Carey
1968).

Methods
Absorption of photodieldrin by algae, A. spiralis, from water. Algal cells (21,000 cells =
25 mg/ml) were exposed in 100 ml of water containing 3.33 ppb of 14C.photodieldrin
(specific activity, 4.3 mCi/mM) for 1, 2, 3, 4, and 8 hr. Three replicates were run for
each experiment. The cells were centrifuged at 18,000 g/ten rain, the water was removed,
and they were then resuspended in the original volume with clean water and recentrifuged.
The pellet of cells was ground with sodium sulfate in 20 ml of benzene-hexane (1 : 1) using
a mortar and pestle. Aliquots of 0.1 ml were counted in ten ml of the scintillation cock-
tail (Khan and Matsumura 1972) using a Packard spectrometer (Model 3390) equipped
with Absolute Activity Analyzer (Model 544) The values in the three replicates were
averaged and then plotted.
 Biological Magnification of Photodieldrin by Food Chain Organisms 291

Absorption of insecticides from water by animals. Water was aged at room temperature
by constant aeration for two to three days before adding the insecticide solution in
methylcellusolve (one ml of insecticide solution/liter of water) to obtain the desired
concentration. Slow aeration of water was continued after adding the animals, the
containers being kept covered with aluminum foil.

Direct absorption of the insecticide from aqueous solutions was studied by exposing
animals in water contained in glass jars. The exposure was continued for a maximum
period of six days. Parallel controls containing "only dieldrin or photodieldrin" (without
animals) and "only animals" (without insecticide) were run to check the loss of the
insecticide from the aqueous solution due to evaporation and adsorption onto the glass
surface as well as the presence of any chlorinated hydrocarbons in test animals. The six-
day experiments showed only three to four percent loss of these insecticides from
aqueous solutions. All of the control animals kept in clean experimental water were free
of any chlorinated hydrocarbon insecticides.

Three fishes (weighing one to two g/fish) were exposed to 20 ppb of insecticide in one
gallon of water. Three crayfish (eight g/animal) were exposed to 30 ppb of the insecticide
in 500 ml of water. One hundred late third instar mosquito larvae, weighing 300 mg,
were exposed for 12 hr to six ppb in 500 ml of water. This particular susceptible strain of
mosquitoes did not metabolize photodieldrin to photodieldrin ketone. Clams (10-12 g/
animal), Daphnia (200 mg/lO0 animals), Simocephalus (400 mg/lO0 animals), Palae-
monetes (1-1.4 g/animal), and Gammarus (500-600 mg/lO0 animals) were exposed for
four days; clams (three animals/two liters) and Daphnia and Simocephalus (500 animals/
500 ml)to six ppb, Gammarus (150 animals/500 ml), and Palaemonetes (ten animals/liter)
to ten ppb of the insecticide.

The exposed animals were rinsed with water and then ground with sand, using a
mortar and pestle, in benzene:hexane (1:1, 100 ml of the solvent per g of animal). The
homogenate was extracted at 80°F for three to four hr in a Soxhlet extraction apparatus.
The extract was filtered through Whatman No. 42 filter paper and concentrated by
evaporation in a current of air. After adding suitable amounts of anhydrous sodium
sulfate, the analyses were made using a gas chromatograph (Model 7300, Packard Instru-
ments, Chicago) equipped with a 63Nickel electron-capture detector. The six-foot glass
column employed was packed with DC 200 (5%) or SE-30 (3%) coated on Chromosorb W
(60/80 mesh). The conditions were: temperature (°C), column 190, injector 200, detector
200; nitrogen flow rate, 30 ml/min. Authentic standards were used to quantitate the
insecticides and their metabolites by measuring the peak area (triangulation method).

Elimination of absorbed photodieldrin by goldfish. Three goldfish, in duplicate, were

exposed for 24 hr to 20 ppb of PD in water. They were then removed, rinsed with clean
distilled water, and transferred to one liter of insecticide-free, clean water. The fish from
clean water were removed at 0 (the time of transfer to clean water), 12, 24, 60, and 96 hr,
rinsed, and frozen until analyzed. The clean water at these time intervals was extracted
with hexane-benzene (1:1) and analyzed by gas chromatography as described earlier.
292 H.M. Khan and M. A. Q. Khan

In vivo metabolism of photodieldrin by minnow and bluegill. Three fish (each weighing
about one g) were exposed to 30 ppb of 14C_photodieldrin (specific activity 4.3 mCi/mM)
in one gal of water for five days. The fish were then rinsed with water and homogenized
in 100 ml of distilled water in an Omni-mixer (Sorvall, Inc.). The homogenate was ex-
tracted twice with one liter of benzene:hexane (1:1). The extract was washed with
100 ml of water, dried with anhydrous sodium sulfate and then evaporated to dryness.
The residue was redissolved in one ml of benzene-hexane and used for further analysis.
The aqueous phase was dried by lyophilization, and the residue was redissolved in one ml
of ethanol-water (1:1) and used for further analysis.

Aliquots (0.1 mt) of the redissolved residue were coumed for radioactivity on a
Packard scintillation spectrometer (Model 3390 with Absolute Activity Analyzer).
Fifty-~l samples of the redissolved residues were applied to 250/~ thick Silica Gel G plates
(2" × 8") which were developed in solvent systems consisting of ethyl acetate-hexane
mixtures (1:1 and 1:3). The crude residue was also run through a ten-g Florisil column
and eluted with hexane and hexane-acetone (10:1). The fractions were analyzed by both
thin-layer and gas chromatography. The plates were scanned on a radiochromatogram
scanner (Packard, Model 7201) and also exposed to no-screen medical X-Ray films
(Kodak Chemicals) which were later developed and fixed.

Results
Absorption and biological magnification of photodieldrin by algae and aquatic
invertebrates. The exposure to photodieldrin solutions showed continuous absorption
and retention of this insecticide by all aquatic organisms. Based on the amount of radio-
activity, the 14C.photodieldri n concentration (ng PD/g) at increasing exposure time, in
algal cells was: 1/2 hr, .932; 1 hr, 1.89; 2 hr, 1.97; 3 hr, 2.13; 4 hr, 2.55; and 8 hr, 2.80.
Thus algae, at this cell concentration, became saturated with PD in between four and
eight hr of exposure. Among invertebrates, the clam, the crayfish, and the shrimp
absorbed much less PD than other invertebrates (Fig. 1). The microcrustacea showed the
highest rates of absorption and accumulation of PD. The rate of absorption, by the
microcrustacea, in the increasing order was: Simocephalus < Gammarus < Daphnia.
Daphnia absorbed PD at about a 60-time higher rate than other microcrustacea.

When the rate of absorption of PD was compared with that of dieldrin using same con-
centration, the former was found to be accumulated at a lower rate than the latter (Fig. 2).
The concentration in the body after 12 hours was: 4/~g D/g vs 2/~g PD/g in the mosquito
larvae and 2/ag D/g vs 1 ~g PD/g in the crayfish. In spite of the lower rates of absorption
and accumulation of PD, it was more toxic (100 percent mortality after 12 hours) than
dieldrin (ten percent mortality after 12 hours) at the same concentration. A similar
difference in rates of absorption of dieldrin and PD was also observed in minnow and
goldfish (Fig. 2).

The biological magnification of PD (ng PD/g of the animal: ng PD/ml of water) in

invertebrates with thick exoskeleton was very low. The crayfish, after 12 hr of exposure,
showed a magnification ratio of eight while shrimps and clams, after 48 hours, showed
values of 29.7 and 3.6, respectively (Table I).
 Biological Magnification of Photodieldrin by Food Chain Organisms 293

Among other invertebrates that tie at lower trophic levels, a biological magnification
ratio of about 1000 was seen with Gammarus and Simocephalus after four days (Table II).
Daphnia showed the highest ratio (63,000) during this period. However, the algae showed
a maximum magnification ratio of only 800.

Absorption and biological magnification of photodieldrin by fishes. Exposure of fishes

to sublethal concentrations of PD showed maximum absorption during 24 hr by the
minnow, the bluegill, and the goldfish, followed by a slow decline of PD in their tissues
up to five days (Fig. 2). Only the livebearer, guppy, kept absorbing PD continuously
during the six-day exposure period.

The biological magnification of PD by fishes showed species-specific differences. The

bluegill and minnow showed a ratio of about 150 after 24 hr which was lowered to 78
and 70, respectively, after four days (Table III). The goldfish absorbed more PD than the
bluegill and minnow, the maximum biological magnification ratio after one day being 600
which was gradually reduced to 325 after six days. The tivebearer, guppy, absorbed PD at
a rate much higher than any other fish giving a biological magnification ratio of 820 after
six days.

~. - 300 "~

x=
1/,/7 []
o
3 200 o-

I I'-II /~ / -1'100

OlJ " I i I I I I I | I I0
10 50 1 O0
Hours of exposure

Fig. 1. Absorption and retention of photodieldrin by fresh-water invertebrates, o - - o

Garnmarus; c J - - a Daphnia, ©---© Simocephalus; A.---A Aedes larvae; ® - - ©
crayfish. Scale on right applies only to Daphnia.
 294 H . M . K h a n and M. A. Q. K h a n

20

10
~O

:5
O

"i ~ i l I I I I l I I I , 1 I ]
10 50 100 150
Hours of exposure

Fig. 2. A b s o r p t i o n a n d r e t e n t i o n of p h o t o d i e l d r i n by fresh-water fishes. o---o guppy;

D ~ c ? goldfish; © ~ © m i n n o w ; A - - - z ~ bluegill.

Biological Magnification of Photodieldrin

Table I.
by Aquatic Invertebrates with Thick Exoskeleton

Biological m a g n i f i c a t i o n ratio a
Hours e x p o s e d Clam Crayfish Shrimp

4 - 3.24 -

8 1.42 5.32 -

12 1.65 8.13 0.82

24 2.52 Dead 0.82

48 3.64 29.71

72 - -

96 4.24 -

a C o n c e n t r a t i o n o f PD in the a n i m a l / c o n c e n t r a t i o n o f PD in t h e m e d i u m
o f e x p o s u r e (water).
 Biological Magnification of Photodieldrin by F o o d Chain Organisms 295

Table II. BiologicaI Magnification of Photodieldrin

by Aquatic Invertebrates at Lower Trophic Levels

Biological magnification ratio a

Hours exposed Daphnia Simocephalus Gammarus Aedes

366

8 -- -- 583

12 . . . . r
666

24 27,300 200 626 Dead

48 34,160 - 802

72 -- 400

96 63,300 1020 1172

aConcentration of PD in the animal/concentration in water.

Table IIl. Biological Concentration of Photodieldrin by l~?esh-WaterFishes

Biological magnification ratio a

Exposure time Bluegill Minnow Goldfish Guppy

12 hrs 57 45 51 400

1 day 133 150 609 517

2 days 118 125 495 568

3 days - 1t5 440 577

4 days 78 70 381 718

6 days - 60 325 820

aConcentration of PD in the fish/concentration in water.

Elimination of absorbed photodieldrin b y goldfish. Up to 30 percent of the PD

initially absorbed by goldfish during the 24 hr-exposure was lost in clean water during
the first 12 hours (Table IV). The decline in body levels o f extractable PD could be either
due to its metabolism to hydrophilic metabolite(s) or its excretion into the medium. No
metabolites were seen in the body extracts with the organic phase using the gas chroma-
296 H.M. Khan and M. A. Q. Khan

tographic analysis. However not all metabolites in the organic phase can elute from the
columns employed. For this purpose radioactive PD was used as described in the following
section. However, substantial amounts of PD were detected in water; the concentration
increased with time and paralled the decline in body residues of PD. It is interesting to
note that after excreting PD during the first 12 hr there was no further decline in the
body concentration of PD up to four days. Apparently a new equilibrium is reached
between internal and external PD concentrations in this fish.

In vivo metabolism of photodieldrin by bluegill and minnow. The slow decline of PD

residues in most fishes while they are kept constantly in PD-containing water or by the
rapid decline of PD in the goldfish during the first 12 hr after their transfer to clean water
indicated the possibility of slow degradation of this toxicant to metabolite(s) not identi-
fiable by gas chromatography. For this reason, the in vivo metabolism of 14C-labeled
PD was studied in bluegill, minnows, and goldfish. Analysis of body residues extracted
with hexane-benzene showed only photodieldrin. The aqueous phase showed about two
percent of the total body radioactivity which could not be extracted with the solvent or
detected by gas chromatography. This indicated the formation of hydrophilic metabolite(s).
Analysis of the water in which the fish were exposed showed mostly photodieldrin; only
about two percent of the radioactivity appeared in the form of water-soluble metabotite(s).
Identification of these metabolites is in progress. Such a low rate of detoxication of PD
cannot account for the decline of body residues of PD in these fishes.

Discussion
Biological magnification is a relative term and depends mainly on the partitioning
characteristics of the particular insecticide between water and the living organism. Since
the aquatic organisms keep absorbing insecticide from the surrounding medium until a

Table IV. Elimination o f A bsorbed Photodieldrin by Goldfish

on Transfer to Insecticide-Free Water

Time PD in fisha PD in water

(hr) Total (/lg) Conc. (/~g/g) (¢lg)

0 14.26 3.63 NIL

12 5.35 2.49 7.86

24 8.46 2.49 -

60 5.13 2.36 8.81

96 9.12 2.57 7.86

aDuplicates of 3 fish exposed to 20 ppb of photodieldrin for 24 hr. They

were then rinsed with distilled water and transferred to clean water.
 Biological Magnification of Photodieldrin by Food Chain Organisms 297

peak or equilibrium is reached, the availability of the insecticide, its concentration, and
its total amount (concentration × volume of water) affect the biological magnification
ratio; the lower the concentration and the larger the volume of water to which the
animals are exposed the higher the magnification ratio (Kenaga 1972). Various physiologi-
cal factors contribute to the absorption of the insecticide. The size is very important; the
smaller the size the greater the surface area-to-volume ratio and thus the greater the
diffusion (Krogh 1945, Prosser and Brown 1961). Other factors affecting this ratio may
include: (1) the feeding mechanisms (e.g., microphagous faltering animals can extract
more insecticides than macrophagous animals); (2) the physical characteristics of the
integument (e.g., soft-bodied animals absorb more insecticide than those with a hard exo-
skeleton); and (3) the age and physiological state of the animal.

Considering these factors it can be mentioned that under identical and comparable
conditions aquatic animals showed differences in the rate of absorption and subsequent
retention of photodieldrin during their continuous exposure to sublethal doses. Among
fishes, the minnow and bluegill absorbed the lowest and guppy the highest amounts. The
peak levels of PD residues in tissues were seen within 24 hr after which they started de-
clining slowly in the case of the minnow, bluegill, and goldfish. This may be due to a
shift in equilibrium between the external and internal PD concentration which declines
in the former after initial absorption by the fish. However, guppies continued absorbing
PD, their tissue levels of PD increasing with time. Since guppies are livebearers (viviparous),
such high levels can have detrimental effects on their embryos and the fry which are ex-
tremely sensitive to chlorinated hydrocarbons (O'Brien 1967). The slower absorption of
PD by minnows and bluegills may be due to the rapid excretion of PD into the water
through their gills. The equilibrium appears to be in the favor of excretion after maximum
levels of PD are reached in their tissues. Excretion of DDT, dieldrin, and lindane through
the gills in goldfish exposed to sublethal doses has been reported (Gackstatter and Weis
1967). The initial elimination of the absorbed PD by the goldfish on its transfer to
uncontaminated water is due to its excretion into the surrounding water. A similar
elimination of 14C.labelle d dieldrin and photodieldrin by Daphnia has also been observed
in this laboratory by Rio and Khan (unpublished data).

The data on biological magnification values of some commonly used cyclodienes re-
ported from other laboratories have been summarized in Table V. The magnification
value of PD obtained here for the bluegill is about half that reported for heptachlor. Our
value for the minnow is about 70-times lower than that reported using a 40-times lower
concentration of dieldrin (Mount and Putnicki 1966). Since PD is absorbed at a ratehalf
that of dieldrin by the minnow (2.5 /~g PD/g vs 4 gg D/g, after 24 hr) our value is com-
parable to the one reported by these authors. The highest magnification value for PD
obtained for the guppy in our studies is still lower than the one reported at almost
comparable concentration of dieldrin for the trout. These may reflect the differences in
the absorption of these cylcodienes between these two species which show the highest
biological magnification.

Invertebrates continued to absorb and retain PD with time; the crayfish, shrimp, and
clam absorbed much tess PD. The low levels of PD in clams cannot be explained. In their
 O0

Table V. Biological Magnification Ratios o f Several Cyclodienes by Aquatic Animals Reported in Literature

Animal Cyclodiene Conc. Magnification Reference

Eastern Oyster Endrin and 1 ppb/10 days 1,000 Wilson (1965)

dieldrin
Oystera Heptachlor 10 ppb/10 days 17,000 Wilson ( 1965 )
Bluegill Heptachlor 50 ppb 300 Cope (1966)
Trout Dieldrin 2.8 ppb 3,300 Holden (I 966) c~
Minnow Dieldrin 15 ppt t 0,000 Mount and Putnicki (1966)
.>
Daphnia b Aldrin 167 ppt/3 days 141,000 Johnson et al. (1971 )
Mayfly (nymphs) b Aldrin 21.3 ppt/3 days 31,000 Johnson et al. (1971) 7~
Chlronomus Aldrin 21.3 ppt/3 days 23,000 Johnson et al. (1971) ~
(larvae)b

aIn running water.

bValues expressed on dry wt. basis.
 Biological Magnification of Photodieldrin by Food Chain Organisms 299

relatives, the oysters, the filtration (Jorgensen and Goldberg 1953, Prosser and Brown
1961) can result in about 1000-fold concentration of dieldrin and endrin in their tissues
in the laboratory and about 18,000-fold in running water (Wilson 1965, Table V). The
low levels of PD in the filter-feeding clams could be due to an effect of PD on the
mechanisms which control filtration or closing of their shell valves. It could be also due to
the lipophobic nature of their tissues and gills which has been observed with other in-
vertebrates (Brodie and Maickel 1961). The low magnification values by other non-filter
feeding crustaceans indicate that penetration of PD through general body surface may
not be critical in biological magnification. The crayfish, in spite of low absorption of PD
are extremely sensitive to this insecticide.

Among small invertebrates Gammarus and Simocephalus showed about 1000-fold and
Daphnia about 63,000-fold magnification of PD. These values are lower than those re-
ported with atdrin for microcrustacea (Johnson et al. t967). Aldrin may be concentrated
at higher rates than PD by these organism because it is more lipophilic than PD (water
solubility in ppb; A = Ca. 27; PD = Ca. 400). However, our values are comparable with
those reported for oysters.

In vivo metabolism of photodieldrin to photodieldrin ketone has been reported in

some insects and mammals (Khan et al. 1969, Klein et al. 1969). However, sublethal
exposure of the organisms used here did not show the formation of photodieldrin ketone.

The lack of metabolism of PD by fishes when exposed to sublethal levels of this

insecticide indicates the stability of this compound in aquatic environments. If organisms
at lower trophic levels are also incapable of detoxifying sublethal doses of PD, the
possibility of contamination of organisms at the upper levels of the food chain due to the
biological concentration is quite obvious. Such studies are in progress in this laboratory.

Acknowledgments

This research was supported by a grant (ES-00808) from the National Institute of
Environmental Health Sciences. Thanks are due to Mr. R. H. Barker and Mr. D. Zumwalt
of the John G. Shedd Aquarium, Chicago, and Mr. R. Lent of Illinois State Hatchery,
Spring Grove, for the supply and maintenance of fishes.

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Manuscript received April 3, 1973; accepted November 23, t973