TOXICITY OF NATURAL PYRETHRINS AND

FIVE PYRETHROIDS TO FISH

WILBUR L. MAUCK and LEE E. OLSON
Fish Pesticide Research Unit
P.O. Box 936
La Crosse, Wisconsin 54601

LEIF L. MARKING
Fish Control Laboratory
P.O. Box 862
La Crosse, Wisconsin 54601

The toxicity of natural pyrethrins and five pyrethroids was determined with coho
salmon (Oncorhynchus kisutch), steelhead trout (Salmo gairdneri), fathead minnow
(Pimephales promelas), channel catfish (Ictalurus punctatus), bluegill (Lepomis raac-
rochirus), and yellow perch (Perca flavescens). The 96-hour LCs0's in static tests at
12~ ranged from 24.6 to 114/zg/1 of natural pyrethrins and from 0.110 to 1,140/zg/1
of pyrethroids. Two pyrethroids, RU-11679 and SBP-1382 (a), were over 10 times
more toxic than pyrethrum extract in the flow-through tests. Coldwater species of fish
were more sensitive than warmwater species to all the compounds. Temperature
(12-22~ influences the toxicity of natural pyrethrin and the pyrethroids. The natural
pyrethrin was more toxic to fish in pH 6.5 than in pH 9.5 water, but the toxicity of
pyrethroids was not influenced in that pH range. The two most toxic pyrethroids,
RU-11679 and SBP-1382, were deactivated more rapidly in water solutions than
natural pyrethrins, S-bioallethrin, dimethrin, and d-trans allethrin.

Natural pyrethrins have been used for controlling insects for many years but were
largely replaced by organochlorine pesticides during World War II. Recently, due to
the persistence of these pesticides in the environment, pyrethrins are regaining
importance for insect control (Bogaard 1969). Structures similar to the naturally
occurring pyrethrins have been synthesized (Casida 1973), and these pyrethroids
have proved to be more toxic to insects, more stable, more species specific, and less
hazardous to mammals than natural pyrethrins (Abernathy and Casida 1973,
Nishizawa 1971). Bioresmethrin is more toxic to houseflies than to rats by a factor
of 32,000 (Elliott 1970). The apparent greater sensitivity of insects is due to
structural configurations of some pyrethroids and the lack of certain metabolic
capabilities of insects (Casida et al. 1971, Miyamato et al. 1971, and Yamamoto et
al. 1971). The mode of action of pyrethroids has been identified as that of a
neuropoison acting on the nerve axon (Narahashi 1971, Yamamoto 1970).

The decomposition products of some pyrethroids also have been identified.

Pyrethroids readily decomposed when irradiated by a sun lamp, in sunlight, and as

Archives of Environmental Contamination 18

and ToxicologyVol. 4, 18-29 (1976)
'~1976 by Springer-Verlag New York Inc.
 Toxicity of Pyrethrins and Pyrethroids to Fish 19

thin films on glass, and decomposition yielded at least 11 products for each structure
(Chen and Casida 1969).

Although natural pyrethrins degraded rapidly in aquatic systems, they are highly
toxic to aquatic organisms. Stoneflies (Pteronarcys californica) are more sensitive
to natural pyrethrins than are three species of freshwater fishes (Bridges and Cope
1965). The pyrethroids, in addition to being more toxic than natural pyrethrins to
insects, are also more toxic to fish. If pyrethroids are dispensed in large-scale
applications as forest or agriculatural insecticides, they may be hazardous to fish.
The objective of this study was to determine and compare the toxicity of natural
pyrethrins and five selected pyrethroids to fish under various environmental condi-
tions of water temperature, hardness, and pH. Additionally, the detoxification rate
for these chemicals in water was determined by fish bioassay.

Materials and methods

Pyrethrum extract and one pyrethroid, SBP-13821 (also known as Resmethrin or

Synthrin), were supplied by S.B. Penick and Company, New York, New York. Four
additional pyrethroids, dimethrin, d-trans allethrin (also known as Bioallethrin),
RU-11679, and S-bioallethrin, were supplied by McLaughlin, Gormley, King Com-
pany, Minneapolis, Minnesota.

Common name Chemical name

Pyrethrum extract (natural mixture of Pyrethrin I, Pyrethrin II, Cinerin I, Cine-

pyrethrins) rin II, Jasmolin l, and Jasmolin II
Dimethrin 2,4-dimethylbenzyl cis, trans-( ++_)-2,2-dimethyl-3-
(2-methylpropenyl) cyclopropanecarboxylate
d-trans allethrin trans-( + )- 2,2-dimeth y l- 3-( 2-meth yl-propen yl)
cyclopropanecarboxylic acid ester with (_)-2-allyl-
4-hydroxy-3-methyl-2-cyclopenten- 1-one
RU-I1679 (5-benzyl-3-furyl) methyl- -trans-(+)- 3- (cyclo-
pentylilidenemethyl)- 2,2- dimethylcyclopropane-
carboxylate
S-bioallethrin trans-( + )-2,2-dimethyl-3-(2-methylpropenyl) cyclo-
propenecarboxylic acid ester with (+)-2-allyl-4-
hydroxy-3- methyl-2-cyclopenten- 1-one
SBP- 1382 (resmethrin) (5-benzyl-3-furyl)methyl cis-trans-( +_)-2,2 -
dimethyl-3-(2-methylpropenyl) cyclopropane-
carboxylate

tReference to trade names does not imply government endorsement of commercial products.
 20 W . L . Mauck et al.

Prior to each static and flow-through test fresh stock solutions of toxicant were
prepared in commercial grade acetone. Static tests were conducted according to the
methods described by Lennon and Walker (1964). Appropriate portions of these
solutions were than pipetted into glass jars containing 15 L of water. Flow-through
tests were conducted in a system described by Mount and Brungs (1967), equipped
with a modified metering device (McAllister et al. 1972). Food was witheld during
the 96-hr period to facilitate comparison of 96-hr LCs0's for static and flow-through
tests. Fish in flow-through tests were offered commercial pellets at a rate of 2% of
body weight per day beginning on day 5.

Influences of water quality on toxicity were investigated. Various water hardnes-

ses were prepared by adding different quantities of mineral salts to deionized water
(Marking 1969) (Table I). Chemical buffers were used to adjust and maintain pH's
6.5, 8.5, and 9.5 (Marking and Dawson 1972). All flow-through tests were con-
ducted with charcoal filtered municipal well water (pH, 7.7-7.9; total hardness as
CaCO3, 280-320 m ~ L ; total alkalinity as CaCo3, 220-260 mg/L). Test temperatures
were maintained (___ I~ by constant temperature water baths surrounding the glass
jars and aquaria.

Coho salmon (Oncorhynchus kisutch), steelhead trout (Salmo gairdneri), fathead

minnow (Pimephales promelas), channel catfish (Ictalurus punctatus), bluegill
(Lepomis macrochirus), and yellow perch (Perca flavescens) from Federal hatch-
eries were kept under a fish culturist's care (Hunn et al. 1968). All fish were
acclimated to the test water and then placed in static test vessels approximately 24 hr
before introducing the toxicant, with two exceptions. For tests to determine deacti-
vation and for flow-through tests, acclimated fish were introduced into chambers
already containing chemical. The average size of fish used ranged from 0.2 to 2.7 g
in static tests and from 0.2 to 2.6 g in flow-through tests.

Table I. Characteristics of Reconstituted Waters

Total
Water type pH range Hardness b Alkalinity b

Very soft 6.4- 6.8 10- 13 10- 13

Soft a 7.2 - 7.6 40 - 48 30 - 35

Hard 7.6- 8.0 .160- 180 1 I 0 - 120

Very hard 8.0 - 8.4 280 - 320 225 - 245

aStandard reconstituted water used in routine toxicity test.

hAs mg/L CaCO 3.
 Toxicity of Pyrethrins and Pyrethroids to Fish 21

Deactivation tests were conducted in soft water at various pH's to obtain data on
the persistence of the natural extract and pyrethroids. A deactivation index was
obtained by dividing the 96-hr LCso of the aged (one week) series by the 96-hr LC~o
of the fresh or reference series (Marking 1972). If the index is approximately one,
the aged solution is as toxic as the fresh solution. If the index is greater than one the
solution has deactivated, and if the index is less than one the solution has increased
in activity.

The method o f Litchfield and Wilcoxon (1949) was used to determine the statisti-
cal LCso (concentration producing 50% mortality) and 95% confidence limits.
Time-independent concentrations (TILCso's) were determined by a modification of
Green's (1965) method. The TILCs0 is an estimate of the concentration at which
50% of the animals exposed would survive indefinitely. Toxicity was calculated for
the formulations rather than for the active ingredients. The percent active ingredient
in the formulations is shown in the tables that follow.

Results

All species of fish treated had different susceptibilities to natural pyrethrins and
pyrethroids. The salmonids were the most sensitive, and fathead minnow and
channel catfish were the most resistant (Table II). Two of the pyrethroids were
particularly toxic to all species: 96-hr LCso'S ranged from 0.110 to 0.635 /~g/L for
RU-11679 and from 0.450 to 2.62 ~g/L for SBP-1382. The natural extract was the
least toxic on the basis of formulation, andd-trans allethrin was least toxic on the
basis of active ingredient.

Temperature affected the biological activity of all the compounds tested. Pyret-
hrum extract, dimethrin, RU-11679, and SBP-1382 were significantly (P = 0.05)
more toxic at 12~ than at 17~ (Table III). Also, dirnethrin and SBP-1382 were
more toxic at 17~ than at 22~ but the toxicity of the natural pyrethrins and
RU-I1679 was not influenced in this temperature range. The biological activity of
dimethrin, RU-11679, and SBP-1382 was two to three times greater at 12~ than at
22~ However, d-trans allethrin and S-bioallethrin were less toxic (although not
significantly) at 12~ than at 17~ The d-trans allethrin was more toxic at 22~
than at 17~ and was about one and a half times more toxic at 22~ than at 12~

Water hardness had little influence on the toxicity of the pyrethroids (Table III).
However, toxicity of the natural extract increased slightly as water hardness in-
creased; the 96-hr LCso decreased significantly from 62.0/.~g/L in very soft water to
46.5 /zg/L in very hard water.

The biological activity of natural pyrethrins increased significantly in acidic

water (Table HI). The 96-hr LCs0 of natural pyrethrins at pH 6.5 (41.0 /zg/L) was
less than half that at pH 9.5 (87.0 /zg/L). The toxicity of the pyrethroids was not
altered significantly by the various pH's, indicating greater molecular stability than
the natural extract at different pH's.
 22 w . L. Mauck et al.

Table II. Toxicity a o f Pyrethrum Extract and Five Pyrethroids to Fish

in Static and Flow-through Tests at 12~

Formulation Species 96-hrLC50 and 95% c o n f i d e n c e limits (/2g/L)

S t a t i c tests Flow-through tests
Pyrethrum Coho salmon 39.0 23.0
extract 33.1-46.0 17.8 - 29.7
(20%) Steelhead t r o u t 24.6 22.5
20.4 - 29.6 19.2 - 26.3
Channel catfish 114 132
9 5 . 0 - 137 1 1 7 - 149
Bluegill 49.0 104
3 9 . 2 - 61.3 8 0 . 3 - 135
Yellow p e r c h < 50.1 44.5
36.4 - 54.3
Dimethrin Channel catfish 1140 165
(96%) 1 0 2 0 - 1280 1 2 6 - 216
Bluegill 37.5 22.3
28.1 - 50.0 16.7 - 29.7
Yellow p e r c h 28.0
21.5 - 36.5
d-trans Coho s a l m o n 22.2 9.40
allethrin 2 0 . 6 - 23.9 7.91 - 11.2
(90%) Steelhead t r o u t 17.5 9.70
13.1 - 23.4 8.00 - 11.6
Channel catfish > 30.1 27.0
22.4 - 32.6
Yellow p e r c h - 9.90
9 . 1 7 - 10.7
RU-11679 Coho salmon 0.635 0.151
(95%) 0.580 - 0.696 O. 132 - 0.173
Steelhead t r o u t 0.110 0.100
0.0910 - 0 . 1 3 4 0.0750 - 0.133
Channel catfish 0.630 0.700
0.402 - 0.853 0.583 - 0.840
Yellow p e r c h - 0.0560 b

S-bioallethrin Fathead minnow 80.0 53.0

(98%) 65.9 - 97.1 35.9 - 78.3
Channel catfish - 14.6
I 0 . 0 - 21.1
Yellow p e r c h 7.80
6.50 - 9.30
SBP-1382 Coho salmon > 1.50 < 0.277
(89%)
Steethead t r o u t 0.450 0.275
0.331 - 0.613 0.237 - 0.319
Bluegitl 2.62 0.750
2.15 - 3.19 0.627 - 0.898
Yellow p e r c h 2.36 0.513
1.96 - 2.84 0.44I - 0.597

a T o x i c i t y based o n total f o r m u l a t i o n
b l n s u f f i c i e n t data to c o m p u t e .
 Table III. Toxicity a of Pyrethrum Extract and Five Pyrethroids to Bluegill (0.8 g) in Static
Toxicity Tests at Various Water Temperatures, Hardnesses, and pH's
Test Conditions 96-hr LC50 and 95% c o n f i d e n c e limits (#g/L) for

Pyrethrum d-trans S-bio-

Temp. Water extract Dimethrin ailethrin RU-11679 allethrin SBP-1382
(~ hardness pit (20%) (96%) (90%) (95%) (98%) (89%)
,.q
22 Soft 7.5 O
58,0 85,0 35,0 0.670 m
5.46
51.5-65.3 67.4-107 31.4-39.0 0.531-0.845 5.01 - 5.95 ,.<

17 Soft 7.5 O
59.0 57.9 47.0 0.580 27.6 4.28
"U
5 0 . 6 - 68.8 4 4 . 4 - 75.5 4 0 . 0 - 55.2 0 . 4 6 0 - 0.731 24.5 - 31.1 3.59 - 5.10

12 Soft 7.5 45,5 30.0 56.0 0,235 33.2 2.33

41.3-50.1 22.4-40.1 44.5-70.5 0.196-0.282 25.0 - 44.1 2 . 0 0 - 2.72
12 Very soft 6.6 62.0 26,0 49.0 0.368 39,0 12L
2,53
53.6-71.7 21.3-31.8 42.5-56.5 0,292-0.464 33.5 - 35.4 2.15 - 2.98 ,.<

12 Hard 7,8 53.5 27,6 49,0 0.230 30,0 2.54

48.6-58.8 20.6-37.0 42.7-56.2 0.176-0.300 25.4 - 35.4 2.15 - 3.00

12 Very hard 8.2 46.5 28.2 42.5 0,278 36.0 2.06

40.4 - 53.6 22.5 - 35.4 33.4 - 54.1 0.220 - 0.352 32.2 - 40.3 1.68 - 2.53

12 Soft 6.5 41,0 24.0 56.0 0,280 > 25.0 2.29

35.4-47.4 19.1 - 3 0 . 2 47.3 - 6 6 . 3 0.223 - 0 . 3 5 2 1.93 - 2.71
12 Soft 9.5 87.0 29.0 60.0 0.257 > 25.0 ' 2.46
80.0 - 94.6 22.7 - 37.0 52.1 - 69.1 -- __b 2.17 - 2.79

a T o x i c i t y based o n total f o r m u l a t i o n .
b l n s u f f i c i e n t data to c o m p u t e . [,O
L,J
24 W. L. M a u c k et al.

Table IV. Toxidty a o/Pyrethrum Extract and Five Pyrethroids to Bluegill (0.8 g) in
Reference and Aged (1 Week) Solutions and the Deactivation
Indices at Various pH's at 12~

96-hr LC50 (/.tg/L) and 95% confidence limits

Deactivation b
Formulation pH Reference solution Aged solution Index

Pyrethrum extract 6.5 41.0 66.0 1.61

(20%) 35.4 - 47.4 58.7 - 74.2
7.5 53.0 56.0 1.06
44.3 - 63.5 47.7 - 65.8
9.5 87.0 90.0 1.03
80.0 - 94.6 76.3 - 106
Dimethrin 6.5 24.0 28.1 1.17
(96%) 19.1 - 3 0 . 2 __ __c
7.5 30.0 28.2 0.94
2 2 . 4 - 40.1 22.1 - 3 5 . 9
9.5 29.0 33.7 1.16
22.7 - 37.0 27.1 - 4 2 . 0
d-trans aHethrin 6.5 56.0 40.0 0.71
(90%) 47.3 - 66.3 3 6 . 0 - 44.1
7.5 56.0 34.3 0.61
44.5 - 70.5 -- --
9.5 60.0 74.0 1.23
52.1 - 69.1 64.5 - 85.0
RU-11679 6.5 0.280 1.25 4.46
(95%) 0.223 - 0.352 0.901 - 1.73
7.5 0.275 0.800 2.91
-- -- 0 . 5 9 0 - 1.09
9.5 0.257 0.530 2.06
-- -- 0.381 - 0 . 7 3 7
S-bioaUethrin 6.5 > 25.0 33.8 < 1.35
(98%) 30.4 - 37.6
7.5 33.2 44.3 1.33
2 5 . 0 - 44.1 3 8 . 2 - 51.3
9.5 > 25.0 53.8 < 2.15
42.9 - 67.4
SBP-1382 d 6.5 2.89 5.00 1.73
(89%) 2.31 - 3.61 4 . 3 5 - 5.75
7.5 2.70 7.20 2.67
2 . 4 2 - 3.01 6 . 0 9 - 8.51
8.5 3.13 6.50 2.08
2.67 - 3.67 5.68 - 7 . 4 4
9.5 2.68 5.35 2.00
2.41 - 2 . 9 8 4.50- 6.37

aToxicity based on total formulation.

96-hr LC50 of aged solutions
bDeactivation Index =
96-hr LC50 of reference solutions
Clnsufficient data to compute.
CtRainbow t r o u t w e r e u s e d i n s t e a d o f bluegill.
 Toxicity of Pyrethrins and Pyrethroids to Fish 25

Deactivation studies demonstrated a definite change in toxicity with time and pH

o f the solution (Table IV). Although the toxic activity of the natural extract de-
creased as pH increased, an additional week of aging did not further change the
toxicity at pH 7.5 and 9.5, as shown by the deactivation indices. At pH 6.5,
however, pyrethrum extract was deactivated during the additional week~ The pyret-
hroids RU-11679 and SBP-1382 were deactivated considerably at all the pH's. The
biological activity of SBP-1382 decreased by about one half at each pH. The
deactivation index for RU-11679 was 2.06 at pH 9.5, but increased to 2.91 at pH
7.5 and 4.46 at pH 6.5 (Table IV). Dimethrin and S-bioallethrin were not deacti-
vated appreciably at any of the pH's, whereas the toxicity of d-trans allethrin
appeared to increase in aged solutions. In general, the two most toxic pyrethroids
(SBP-1382 and RU-11679) were deactivated faster than the other pyrethroids and
natural pyrethrins.

Table V. Toxicityaof the Pyrethroid R U-11679 to Fish

7o
in Flow-through Tests at 1. C

Exposure LC50 (Jag/L) and 95% confidence limits

(days) Coho salmon (15 g) Channel catfish (8.7 g)

5 0.176 0.750
0.152-0.204 0.562-0.999

10 0.160 0.410
0.142-0.180 0.350-0.480

15 0.109 0.410
0.100-0.118 0.350 - 0.480

20 0.0930 0.305
0.0860- 0.100 0.248- 0.374

25 0.0890 0.305
0.0790-0.0990 0.248- 0.374

30 0.0690 0.305
0.0610- 0.0770 0.248- 0.374

35 0.0640 __c
0.0570-0.0720

TILCso b 0.0293 0.194

aToxicity based on total formulation.

bBased on a modification of Green's (1965) method for the estimation of toxi-
city over an indefinite time period.
CExposure terminated at 30 days.
 26 W . L . Mauck et al.

The 96-hr toxicity of pyrethrum extract and pyrethroids was about two to four
times greater in flow-through tests than in static tests (Table II), which correlates
with the deactivation of these compounds in static aqueous solutions. Also, larger
coho salmon and channel catfish were less sensitive than smaller ones to RU-11679.

The time-independent toxicity for RU-11679 was determined in long-term flow-

through tests by exposing coho salmon and channel catfish. The Time-independent
LC~o estimated for channel catfish was about six times greater than for coho salmon
(Table V). The toxicity of RU-11679 to channel catfish stabilized between 15 and 20
days of exposure with a predicted time-independent LCs0 of 0.194 ~g/L, whereas the
toxicity to coho salmon appeared to stabilize between 30 and 35 days with a time-
independent LCs0 of 0.0293 /~g/L.

Discussion
The pyrethroids RU-11679 and SBP-1382 were significantly more toxic than the
other pyrethroids or pyrethrum extract to fish. RU-11679 was found to be 4 to 10
times more toxic than SBP-1382 against fish and about 65 times more active than
pyrethrum extract. Nishizawa (1971) stated that topical application of Resmethrin
(SBP-1382) demonstrated an even greater insecticidal activity than pyrethrum ex-
tract against the housefly, Musca domestica; the mosquito, Culex pipen; and the
cockroach, Blattela sp.

Species specificity was demonstrated by all the compounds examined. Bridges

and Cope (1965) correspondingly reported that pyrethrum was more toxic to rainbow
trout than to channel catfish and bluegill. In addition, they found the stonefly,
Pteronarcys sp., to be 56 times more sensitive than rainbow trout to pyrethrum
extract (96-hr LCso's of 1.0 mg/L and 56 mg/L, respectively). Elliott (1970) discus-
sed the insecticidal activity and specificity of the pyrethroids in relation to their
structure and stated the pyrethroid toxicity to insects is closely related to the size and
nature of the ring and that the toxicity is greatest in furan or cyclopentenolone
derivatives.

Changes in water temperature affected the biological activity of pyrethrum extract

and pyrethroids. Toxicity to fish was greater at the lower water temperatures for all
compounds except d-trans allethrin. Narahashi (1971) similarly concluded that the
insecticidal activity of pyrethroids is greater at low than at high temperatures and
that increased metabolic processes of fish at higher temperatures may accelerate the
degradation of the pyrethroids. Conceivably, sensitivity of the nervous system to
pyrethroids varies with temperature, as suggested by Narahashi (1971).

Biological activity of the natural pyrethrins was altered considerably by different

pH's and to a lesser extent by different water hardnesses. The piscicidal activity of
the natural pyrethrins decreased in the more alkaline water. Toxicity of the pyret-
hroids was not affected by pH or water hardness within 96 hr. However, pH did
influence the rate of degradation of some of these compounds. RU-11679 was
detoxified faster in acid (deactivation index of 4.46) than in alkaline (2.06) water,
 Toxicity of Pyrethrins and Pyrethroids to Fish 27

whereas d-trans allethrin was detoxified faster in alkaline (1.23) than in acid (0.71)
water. The deactivation rate of the other pyrethroids was influenced little by diffe-
rent pH's. Nishizawa (1971) showed the degradation of Resmethrin to be very slight
and the pyrethroid to be more stable than pyrethrum extract.

The time-independent concentration (TILCso) was termed the asymptotic LCso by

Ball (1967) and was defined by Brown (1973) as the concentration at which the LCs0
becomes constant for a prolonged period. The particular concentration is of interest
because the fish demonstrate the capacity to detoxify the pesticide at the time-
independent LCs0. This concentration was about one-sixth of the 5-day LCs0 with
coho salmon and one fourth of the 5-day LCso with channel catfish.

Because of their greater toxicity to fish, pyrethroids may pose a greater hazard to
aquatic life than pyrethrum extract. An aquatic ecosystem which has relatively cold
water and supports coldwater fish would be the most susceptible to pyrethroid
toxicity, although these compounds appear to be deactivated rapidly in water.

Conclusions
1. Pyrethrum extract and pyrethroids are highly toxic to fish; the order from most
toxic to least toxic based on active ingredient is RU-11679, SBP-1382, pyret-
hrum extract, S-bioallethrin, dimethrin, and d-trans allethrin.
2. All of the compounds are more toxic to salmonids than to warm water fishes
under the same test conditions.
3. Pyrethrum extract and four of the pyrethroids were more toxic in cold (12~
than in warm (22~ water, whereas d-trans allethrin was more toxic in warm
than in cold water.
4. Pyrethrum extract was more toxic to fish in low pH (6.5) than in high pH (9.5)
water; the toxicity of pyrethroids was not influenced by pH in the range of 6.5
to 9.5.
5. The two most toxic pyrethroids, RU-11679 and SBP-1382, were deactivated
more rapidly than pyrethrum extract and other pyrethroids.
6. In general, the toxicity of dimethrin and d-trans allethrin was least influenced
by temperature, water hardness, and pH.
7. The time-independent LCso's for RU-I1679 were 0.0293 /zg/L against coho
salmon and 0.194 /zg/L against channel catfish; these values are about one-
fifth of the five-day LC50.

References

Abernathy, C. O., and J. E. Casida: Pyrethroid insecticides: esterase cleavage in

relation to selective toxicity. Science 179, 1235 (1973).
Ball, I. R.: The relative susceptibilities of some species of freshwater fish to
poisons. Water Res. 1, 767 (1967).
28 W.L. Mauck et al.

Bogaard, T.: A comeback for pyrethrum? Agr. Chem. 24, 23 (1969).

Bridges, W. R., and O. B. Cope: The relative toxicities of similar formulations of
pyrethrum and rotenone to fish and immature stoneflies. Pyrethrum Post 8, 3
(1965).
Brown, V. M.: Bioassay techniques and environmental chemistry. 1 ed. Ann Arbor,
Mich.: Ann Arbor Science Publishers Inc. (1973).
Casida, J. E.: Pyrethrum, the natural insecticide. 1 ed. New York-London:
Academic Press (1973).
Casida, J. E., E. C. Kimmel, M. Elliott, and N. F. Janes: Oxidative metabolism of
pyrethrins in mammals. Nature 230, 326 (1971).
Chen, Y. L., and J. E. Casida: Photodecomposition of pyrethrin I, allethrin,
phthalthrin, and dimethrin modifications in the acid moiety. J. Agr. Food
Chem. 17, 208 (1969).
Elliott, M.: The relationship between the structure and the activity of pyrethroids.
Bull. World Health Organ. 44, 315 (1970).
Green, R. H.: Estimation of tolerance over an indefinite time period. Ecology 46,
887 (1965).
Hunn, J. B., R. A. Schoettger, and E. W. Whealdon: Observations on the handling
and maintenance of bioassay fish. Prog. Fish-Cult. 30, 164 (1968).
Lennon, R. E., and C. R. Walker: Laboratories and methods for screening fish-
control chemicals. U.S. Fish Wildl. Serv., Invest. Fish Control No. 1 and
Circ. No. 185, 1 (1964).
Litchfield, J. T., and F. Wilcoxon: A simplified method of evaluating dose-effect
experiments. J. Pharmacol. Exp. Ther. 96, 99 (1949).
Marking, L. L.: Toxicological assays with fish. Bull. Wildl. Dis. Assoc. 5, 291
(1969).
Marking, L. L.: Methods of estimating the half-life of biological activity of toxic
chemicals in water. U.S. Fish Wildl. Serv., Invest. Fish Control No. 46, 9
(1972).
Marking L. L., and V. K. Dawson: The half-life of biological activity of antimycin
determined by fish bioassay. Trans. Am. Fish. Soc. 101, 100 (1972).
McAllister, W. A. Jr., W. L. Mauck, and F. L. Mayer Jr.: A simplified device for
metering chemicals in intermittent-flow bioassays. Trans. Am. Fish Soc. 101,
555 (1972).
Miyamato, J., T. Nishida, and K. Ueda: Metabolic fate of resmethrin, 5-
benzyl-3-furylmethyl dl-trans chry.santhemate in the rat. Pest. Biochem.
Physiol. 1, 296 (1971).
Mount, D. I., and W. A. Brungs: A simplified dosing apparatus for fish toxicology
studies. Water Res. 1, 21 (1967).
Narahashi, T.: Mode of action of pyrethroids. Bull. World Health Organ. 44, 337
(1971).
 Toxicity of Pyrethrins and Pyrethroids to Fish 29

Nishizawa, Y.: Development of new synthetic pyrethroids. Bull. World Health

Organ. 44, 325 (1971).
Yamamoto, I.: Mode of action of pyrethroids, nicotinoids, and rotenoids. Ann. Rev.
Entomol. 15, 257 (1970).
Yamamoto, I., M. Elliott, and J. E. Casida: The metabolic fate of pyrethrin I,
pyrethrin II, and allethrin. Bull. World Health Organ. 44, 347 (1971).

Manuscript received July 8, 1974; accepted November 11, 1974.