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Diss Factsheets

Environmental fate & pathways

Bioaccumulation: aquatic / sediment

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Administrative data

Link to relevant study record(s)

Reference
Endpoint:
bioaccumulation in aquatic species: fish
Type of information:
experimental study
Adequacy of study:
key study
Study period:
1992
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
test procedure in accordance with generally accepted scientific standards and described in sufficient detail
Qualifier:
according to guideline
Guideline:
OECD Guideline 305 C (Bioaccumulation: Test for the Degree of Bioconcentration in Fish)
GLP compliance:
no
Specific details on test material used for the study:
d-Phenothrin (3-phenoxybenzyl (1R)-cis,trans-chrysanthemate)(chemical purity 93.5%) was used as a test compound. The optical purity of 1R isomer was 96.3% when determined by HPLC (Shimadzu LC-6A, Sumipax 0A-2000 column with hexane/1,2-dichloroethane (500/1)). The d-cis:d-trans isomer ratio was 1:4 when determined by GC-FID (Shimadzu GC-9A, QF-1 capillary column).
Piperonyl butoxide, other reagents and solvents were purchased from Wako Pure Chemical Co.,Ltd.
Radiolabelling:
no
Vehicle:
yes
Remarks:
Castor oil
Details on preparation of test solutions, spiked fish food or sediment:
Exposure was conducted in a dynamic way as described in the OECD test guideline, No. 305C: 4.3 or 0.43 ppb of d-phenothrin solution, corresponding to 0.86 or 0.086 ppb and 3.4 or 0.34 ppb of d-cis and d-trans isomers, respectively, prepared with castor oil (Nikko Chemical) as an emulsifier was introduced into a 100-L glass aquarium, where 20 yearling carp (Cyprinus carpio, about 20 g body weight, 3% mean lipid content) were maintained. The renewal rate was set at 14.4 times/day. During 8 weeks exposure, fish and water samples were taken at the specified intervals.
To clarify the effect of metabolism on bioconcentration, another exposure experiment at 0.43 ppb of d-phenothrin under similar conditions but in the presence of 1.0 ppm of piperonyl butoxide was conducted for 4 weeks.
Test organisms (species):
Cyprinus carpio
Details on test organisms:
carps of about 20 g weight and 3% lipid content
Route of exposure:
aqueous
Test type:
flow-through
Water / sediment media type:
natural water: freshwater
Hardness:
not reported
Test temperature:
not reported, assumed being 20 °C
pH:
not reported, assumed being neutral, pH 7
Dissolved oxygen:
not reported
TOC:
not reported
Salinity:
not reported
Conductivity:
not reported
Details on test conditions:
Reference was made to OECD 305C method, without disclosing experimental details (see above)
Nominal and measured concentrations:
Average actual concentrations of d-cis and d-trans isomers of the test compound in water were 0.72 and 3.3 ppb at nominal concentrations of 0.86 and 3.4 ppb or 4.3 ppb of d-phenothrin and 0.084 and 0.31 ppb at 0.086 and 0.34 ppb or 0.43 ppb, respectively.
Reference substance (positive control):
no
Lipid content:
ca. 3 %
Time point:
start of exposure
Conc. / dose:
0.86 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
480 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 14 days exposure
Conc. / dose:
0.86 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 450 - <= 470 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 28 days exposure
Conc. / dose:
0.86 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 530 - <= 610 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 42 days exposure
Conc. / dose:
0.86 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 320 - <= 420 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis isomer after 56 days exposure
Conc. / dose:
3.4 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 330 - <= 360 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 14 days exposure
Conc. / dose:
3.4 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 320 - <= 370 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 28 days exposure
Conc. / dose:
3.4 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
400 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 42 days exposure
Conc. / dose:
3.4 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 270 - <= 320 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 56 days exposure
Conc. / dose:
0.086 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 490 - <= 670 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 14 days exposure
Conc. / dose:
0.086 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 660 - <= 730 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 28 days exposure
Conc. / dose:
0.086 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 380 - <= 600 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 42 days exposure
Key result
Conc. / dose:
0.086 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 330 - <= 500 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: cis-isomer after 56 days exposure
Conc. / dose:
0.34 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 320 - <= 500 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 14 days exposure
Conc. / dose:
0.34 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 290 - <= 490 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 28 days exposure
Conc. / dose:
0.34 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 280 - <= 530 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 42 days exposure
Key result
Conc. / dose:
0.34 µg/L
Temp.:
ca. 20 °C
pH:
7
Type:
BCF
Value:
>= 210 - <= 340 dimensionless
Basis:
whole body w.w.
Time of plateau:
14 d
Calculation basis:
steady state
Remarks on result:
other: trans-isomer after 56 days exposure
Results with reference substance (positive control):
not appliied
Details on results:
Fish showed no symptoms of intoxication during the experimental period. The concentration of each isomer in carp increased rapidly and reached a plateau after 2 weeks exposure, as shown in Fig. 1 in the publication. The observed BCF values showed no clear dependency on the exposure concentrations of d-phenothrin, but remarkable differences between isomers, as shown in Table 1 in the publication.
All the fish measured indicates higher BCF values for the d-cis than d-trans isomer by 1.1 to 2.2-fold. Statistical analysis (the t-test for matched pairs) reveals the difference to be significant at 0.1% level. When 0.43 ppb of the test compound was exposed in the presence of piperonyl butoxide to carp, the BCF values of the d-cis isomer clearly increased, but no significant change was observed for the d-trans isomer (BCF cis/trans ratio: 11 - 20), as shown in Table 2. In exposed fish, piperonyl butoxide was detected at the concentrations of 81 to 110 ppm.
In this experiment, average actual concentrations of the d-cis and d-trans isomers of the test compound in water were 0.080 and 0.30 ppb (at nominal concentrations of 0.086 and 0.34 ppb), and no symptom of intoxication was observed for fish during exposure. As shown in Fig. 2, a bioconcentration plateau was also confirmed after 2 weeks exposure.

In this study, a certain difference in BCF's between d-cis and d-trans isomers is observed. The difference is not so large, but statistically significant at 0.1% level. A possible explanation for the difference can be done by considering the effect of metabolism on bioconcentrations of the isomers. Elimination of the compound by biotransformation will be described by a following BCF equation of the two-compartment bioconcentration model:

BCF : Cf(oo)/Cw(oo) = K1/(K2+K3) ( 1 )

where Cf(oo) and Cw(oo) are the concentrations of the compound in fish and water, respectively at a steady state, K 1 and K 2 uptake and elimination rate constants, and K 3 an elimination rate constant by biotransformation. The equation suggests that the higher rate in biotransformation results in the lower BCF value in fish. The comparative biotransformation of 14C-labeled d-cis or d-trans-isomer in carp was investigated by Takimoto et. al. (1986). Both isomers were degraded rapidly and almost completely excreted from fish within one week. Based on the observations for the distribution of 14C, the d-trans isomer was metabolized more rapidly than the d-cis isomer, as reported similarly for mammals. This observation well explains lower BCF value of the d-trans than the d-cis isomer in the present study: The higher metabolic, therefore, disappearance rate of the d-trans isomer should have resulted in the lower BCF value than the d-cis isomer. The major metabolic reactions of d-phenothrin in carp were ester cleavage, oxidations at 4'-position of the alcohol moiety and at the methyl group of the acid moiety. Ester-cleaved or hydrolyzed metabolites were principal products of the d-trans isomer (e.g. sulfate conjugate of 3-(4'- hydroxyphenoxy)-benzoic acid amounting to 47% of the identified metabolites), whereas oxidized products were mostly formed from the d-cis isomer (e.g. glucuronide conjugate of 4'-OH-, desphenyl-, and 4'-OH-vt-alc-c-phenothrin amounting to 77%).

When exposure is conducted in the presence of piperonyl butoxide, a considerable elevation of the BCF value is observed for the d-cis isomer (Table 2). Since piperonyl butoxide is well known as an inhibitor of microsomal oxygenase and the d-cis isomer is metabolized mainly by oxidation as mentioned above, the elevation observed here should be attributable to a reduced oxidative reaction of the inhibited enzyme. The contribution of biotransformation to the elimination (i.e. K3/K 2) was calculated to be 2.3 to 11 by introducing the observed BCF values into the eq.(1) and by setting the rate constant K3 to be 0 when exposure was conducted in the presence of piperonyl butoxide.

Thus, a metabolic effect on bioconcentration was clearly indicated for the d-cis isomer whose metabolism proceeds mainly through oxidation as compared with the d-trans isomer.

The d-trans isomer, on the other hand, did not show such elevation because it followed a rapid ester cleavage or hydrolysis, which has no direct relations to the oxidizing enzyme.

Validity criteria fulfilled:
yes
Conclusions:
The study mainly focused on investigating the bioconcentration differences of the cis- and trans-isomer in carp showing that BCF values for the cis-isomer are slightly, but significantly higher than for the trans-isomer. A steady state plateau was reached quickly within 14 days and BCF values for the cis- and trans-isomers as average from 14 - 56 days were ~ 470 and ~ 350 at concentration of 0.86 and 3.4 ppb, respectively. BCF values at a ten-fold lower concentration were not significantly different.
Executive summary:

This study clearly demonstrated that the BCF value of d-cis phenothrin in carp was significantly higher than the d-trans isomer and an exposure in the presence of piperonyl butoxide resulted in an elevated BCF value for the d-cis isomer, but no remarkable change in BCF's was observed for the d-trans isomer.

Considering an inhibited oxidative metabolism for the d-cis isomer, the result obtained here was well explained and a significance of metabolism in bioconcentration phenomenon was exemplified.

A steady state plateau was reached quickly within 14 days and BCF values for the cis- and trans-isomers as average from 14 - 56 days were ~ 470 and ~ 350 at concentration of 0.86 and 3.4 ppb, respectively. BCF values at a ten-fold lower concentration were not significantly different.

Description of key information

A published study (Miyamoto, 1992) mainly focused on investigating the bioconcentration differences of the cis- and trans-isomer in carp showing that BCF values for the cis-isomer are slightly, but significantly higher than for the trans-isomer. A steady state plateau was reached quickly within 14 days and BCF values for the cis- and trans-isomers as average from 14 - 56 days were ~ 470 and ~ 350 at concentration of 0.86 and 3.4 ppb, respectively. BCF values at a ten-fold lower concentration were not significantly different. Thus, an effective metabolistic pathway as suggested by Takimoto et. al (1986) following 14C-investigations, was considered plausible, contributing to an efficient eleimination from fish tissue.

Key value for chemical safety assessment

BCF (aquatic species):
410 dimensionless

Additional information