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EC number: 946-945-0 | CAS number: -
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Bioaccumulation: aquatic / sediment
Administrative data
Link to relevant study record(s)
- 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. - 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.
Reference
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.
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
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