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EC number: 257-848-1 | CAS number: 52320-66-8
- 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
Short-term toxicity to aquatic invertebrates
Administrative data
Link to relevant study record(s)
- Endpoint:
- short-term toxicity to aquatic invertebrates
- Type of information:
- (Q)SAR
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification
- Justification for type of information:
- QMRF report has been attached
- Qualifier:
- according to guideline
- Guideline:
- other: Estimated data
- Principles of method if other than guideline:
- Prediction was done using the OECD QSAR toolbox version 3.4
- GLP compliance:
- not specified
- Specific details on test material used for the study:
- - Name of test material (IUPAC name): 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide
- Molecular formula: C18H17ClN4O5
- Molecular weight: 404.808 g/mol
- Smiles notation: O=C(Nc1ccc(OCC)cc1)[C@@H](\N=N\c1c([N+](=O)[O-])cc(cc1)Cl)C(=O)C
- InChl: 1S/C18H17ClN4O5/c1-3-28-14-7-5-13(6-8-14)20-18(25)17(11(2)24)22-21-15-9-4-12(19)10-16(15)23(26)27/h4-10,17H,3H2,1-2H3,(H,20,25)/b22-21+
- Substance type: Organic
- Physical state: Solid - Analytical monitoring:
- not specified
- Vehicle:
- not specified
- Test organisms (species):
- Daphnia magna
- Test type:
- static
- Water media type:
- freshwater
- Total exposure duration:
- 48 h
- Reference substance (positive control):
- not specified
- Key result
- Duration:
- 48 h
- Dose descriptor:
- EC50
- Effect conc.:
- 0.134 mg/L
- Nominal / measured:
- estimated
- Conc. based on:
- not specified
- Basis for effect:
- other: Intoxication
- Remarks on result:
- other: Other details not known
- Validity criteria fulfilled:
- not specified
- Conclusions:
- Based on the immobility of test organism the EC50 value was estimated to be 0.133 mg/l when 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide exposed to daphnia magna for 48 hrs.
- Executive summary:
Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the seven closest read across substances, toxicity on daphnia magna was predicted for 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8). Based on the immobility of test organism the EC50 value was estimated to be 0.133 mg/l when 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide exposed to daphnia magna for 48 hrs.
Based on this value it can be concluded that the substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamideis considered to be toxic to aquatic environment and can classified as aquatic acute 1 as well as chronic 1 category as per the criteria mentioned in CLP regulation.
Reference
The
prediction was based on dataset comprised from the following
descriptors: EC50
Estimation method: Takes average value from the 7 nearest neighbours
Domain logical expression:Result: In Domain
(((((((("a"
or "b" or "c" or "d" or "e" )
and ("f"
and (
not "g")
)
)
and "h" )
and "i" )
and ("j"
and (
not "k")
)
)
and ("l"
and (
not "m")
)
)
and ("n"
and (
not "o")
)
)
and ("p"
and "q" )
)
Domain
logical expression index: "a"
Referential
boundary: The
target chemical should be classified as Radical AND Radical >> Radical
mechanism via ROS formation (indirect) AND Radical >> Radical mechanism
via ROS formation (indirect) >> Nitroarenes with Other Active Groups AND
SN1 AND SN1 >> Nucleophilic attack after diazonium or carbenium ion
formation AND SN1 >> Nucleophilic attack after diazonium or carbenium
ion formation >> Nitroarenes with Other Active Groups AND SN1 >>
Nucleophilic attack after reduction and nitrenium ion formation AND SN1
>> Nucleophilic attack after reduction and nitrenium ion formation >>
Nitroarenes with Other Active Groups AND SN2 AND SN2 >> SN2 attack on
activated carbon Csp3 or Csp2 AND SN2 >> SN2 attack on activated carbon
Csp3 or Csp2 >> Nitroarenes with Other Active Groups by DNA binding by
OASIS v.1.4
Domain
logical expression index: "b"
Referential
boundary: The
target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion
formation AND SN1 >> Nitrenium Ion formation >> Aromatic azo AND SN1 >>
Nitrenium Ion formation >> Aromatic nitro by DNA binding by OECD
Domain
logical expression index: "c"
Referential
boundary: The
target chemical should be classified as Acylation AND Acylation >>
Acylation involving an activated (glucuronidated) carboxamide group AND
Acylation >> Acylation involving an activated (glucuronidated)
carboxamide group >> Carboxylic Acid Amides AND Acylation >> Direct
acylation involving a leaving group AND Acylation >> Direct acylation
involving a leaving group >> Carboxylic Acid Amides AND Acylation >>
Ester aminolysis AND Acylation >> Ester aminolysis >> Amides AND AN2 AND
AN2 >> Michael-type addition to quinoid structures AND AN2 >>
Michael-type addition to quinoid structures >> Carboxylic Acid Amides
by Protein binding by OASIS v1.4
Domain
logical expression index: "d"
Referential
boundary: The
target chemical should be classified as Acylation AND Acylation >>
Direct Acylation Involving a Leaving group AND Acylation >> Direct
Acylation Involving a Leaving group >> Acetates AND SN2 AND SN2 >> SN2
reaction at sp3 carbon atom AND SN2 >> SN2 reaction at sp3 carbon atom
>> Alkyl diazo by Protein binding by OECD
Domain
logical expression index: "e"
Referential
boundary: The
target chemical should be classified as Amides by Aquatic toxicity
classification by ECOSAR
Domain
logical expression index: "f"
Referential
boundary: The
target chemical should be classified as Acylation AND Acylation >>
Acylation involving an activated (glucuronidated) carboxamide group AND
Acylation >> Acylation involving an activated (glucuronidated)
carboxamide group >> Carboxylic Acid Amides AND Acylation >> Direct
acylation involving a leaving group AND Acylation >> Direct acylation
involving a leaving group >> Carboxylic Acid Amides AND Acylation >>
Ester aminolysis AND Acylation >> Ester aminolysis >> Amides AND AN2 AND
AN2 >> Michael-type addition to quinoid structures AND AN2 >>
Michael-type addition to quinoid structures >> Carboxylic Acid Amides
by Protein binding by OASIS v1.4
Domain
logical expression index: "g"
Referential
boundary: The
target chemical should be classified as Acylation >> Acylation involving
an activated (glucuronidated) ester group OR Acylation >> Acylation
involving an activated (glucuronidated) ester group >> Arenecarboxylic
Acid Esters OR Acylation >> Acylation involving an activated
(glucuronidated) sulfonamide group OR Acylation >> Acylation involving
an activated (glucuronidated) sulfonamide group >> Arenesulfonamides OR
Acylation >> Direct acylation involving a leaving group >> Azlactones
and unsaturated lactone derivatives OR Acylation >> Direct acylation
involving a leaving group >> Carbamates OR Acylation >> Direct
acylation involving a leaving group >> N-Carbonyl heteroaryl amines OR
Acylation >> Direct acylation involving a leaving group >>
N-Carbonylsulfonamides OR Acylation >> Ester aminolysis or thiolysis OR
Acylation >> Ester aminolysis or thiolysis >> Carbamates OR Acylation
>> Ring opening acylation OR Acylation >> Ring opening acylation >>
beta-Lactams OR AN2 >> Michael-type addition to quinoid structures >>
N-Substituted Aromatic Amines OR AN2 >> Michael-type addition to quinoid
structures >> Substituted Anilines OR AN2 >> Michael-type addition to
quinoid structures >> Substituted Phenols OR AN2 >> Nucleophilic
addition at polarized N-functional double bond OR AN2 >> Nucleophilic
addition at polarized N-functional double bond >> Arenesulfonamides OR
AN2 >> Nucleophilic addition to alpha, beta - unsaturated carbonyl
compounds OR AN2 >> Nucleophilic addition to alpha, beta - unsaturated
carbonyl compounds >> Propargyl Alcohol derivatives OR AN2 >>
Nucleophilic addition to pyridonimine tautomer of aminopyridoindoles or
aminopyridoimidazoles (hypothesized) OR AN2 >> Nucleophilic addition to
pyridonimine tautomer of aminopyridoindoles or aminopyridoimidazoles
(hypothesized) >> Heterocyclic Aromatic Amines OR Michael addition OR
Michael addition >> Michael addition on conjugated systems with electron
withdrawing group OR Michael addition >> Michael addition on conjugated
systems with electron withdrawing group >> alpha,beta-Carbonyl compounds
with polarized double bonds OR No alert found OR Nucleophilic addition
OR Nucleophilic addition >> Addition to carbon-hetero double bonds OR
Nucleophilic addition >> Addition to carbon-hetero double bonds >>
Ketones OR Radical reactions OR Radical reactions >> ROS generation and
direct attack of hydroxyl radical to the C8 position of nucleoside base
OR Radical reactions >> ROS generation and direct attack of hydroxyl
radical to the C8 position of nucleoside base >> Heterocyclic Aromatic
Amines OR Schiff base formation OR Schiff base formation >> Direct
acting Schiff base formers OR Schiff base formation >> Direct acting
Schiff base formers >> 1,2-Dicarbonyls and 1,3-Dicarbonyls OR Schiff
base formation >> Schiff base on pyrazolones and pyrazolidinones OR
Schiff base formation >> Schiff base on pyrazolones and pyrazolidinones
>> Pyrazolones and Pyrazolidinones OR SE reaction (CYP450-activated
heterocyclic amines) OR SE reaction (CYP450-activated heterocyclic
amines) >> Direct attack of arylnitrenium cation to the C8 position of
nucleoside base OR SE reaction (CYP450-activated heterocyclic amines)
>> Direct attack of arylnitrenium cation to the C8 position of
nucleoside base >> Heterocyclic Aromatic Amines OR SN2 OR SN2 >>
Interchange reaction with sulphur containing compounds OR SN2 >>
Interchange reaction with sulphur containing compounds >> Thiols and
disulfide compounds OR SN2 >> Nucleophilic substitution at sp3 carbon
atom OR SN2 >> Nucleophilic substitution at sp3 carbon atom >>
(Thio)Phosphates OR SN2 >> Nucleophilic substitution at sp3 carbon atom
>> alpha-Activated haloalkanes OR SN2 >> SN2 Reaction at a sp3 carbon
atom OR SN2 >> SN2 Reaction at a sp3 carbon atom >> Activated alkyl
esters and thioesters OR SN2 >> SN2 reaction at a sulfur atom OR SN2 >>
SN2 reaction at a sulfur atom >> Isothiazolidin-3-ones (sulphur) and
Isothiazolone derivatives OR SR reaction (peroxidase-activated
heterocyclic amines) OR SR reaction (peroxidase-activated heterocyclic
amines) >> Direct attack of arylnitrenium radical to the C8 position of
nucleoside base OR SR reaction (peroxidase-activated heterocyclic
amines) >> Direct attack of arylnitrenium radical to the C8 position of
nucleoside base >> Heterocyclic Aromatic Amines by Protein binding by
OASIS v1.4
Domain
logical expression index: "h"
Referential
boundary: The
target chemical should be classified as Class 3 (unspecific reactivity)
by Acute aquatic toxicity classification by Verhaar (Modified) ONLY
Domain
logical expression index: "i"
Referential
boundary: The
target chemical should be classified as Reactive unspecified by Acute
aquatic toxicity MOA by OASIS ONLY
Domain
logical expression index: "j"
Referential
boundary: The
target chemical should be classified as Amides by Aquatic toxicity
classification by ECOSAR
Domain
logical expression index: "k"
Referential
boundary: The
target chemical should be classified as Acid moiety by Aquatic toxicity
classification by ECOSAR
Domain
logical expression index: "l"
Referential
boundary: The
target chemical should be classified as Amides by Aquatic toxicity
classification by ECOSAR
Domain
logical expression index: "m"
Referential
boundary: The
target chemical should be classified as Nitro-/Nitroso-Benzamides by
Aquatic toxicity classification by ECOSAR
Domain
logical expression index: "n"
Referential
boundary: The
target chemical should be classified as Amides by Aquatic toxicity
classification by ECOSAR
Domain
logical expression index: "o"
Referential
boundary: The
target chemical should be classified as Vinyl/Allyl Ethers by Aquatic
toxicity classification by ECOSAR
Domain
logical expression index: "p"
Parametric
boundary:The
target chemical should have a value of log Kow which is >= 2.72
Domain
logical expression index: "q"
Parametric
boundary:The
target chemical should have a value of log Kow which is <= 6.45
Description of key information
Based on the prediction done using the OECD QSAR toolbox version 3.4 with log kow as the primary descriptor and considering the seven closest read across substances, toxicity on daphnia magna was predicted for 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8). Based on the immobility of test organism the EC50 value was estimated to be 0.133 mg/l when 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide exposed to daphnia magna for 48 hrs. Based on this value it can be concluded that the substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamideis considered to be toxic to aquatic environment and can classified as aquatic acute 1 as well as chronic 1 category as per the criteria mentioned in CLP regulation.
Key value for chemical safety assessment
Fresh water invertebrates
Fresh water invertebrates
- Effect concentration:
- 0.133 mg/L
Additional information
Various predicted data for the target compound 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8) and experimental studies for supporting weight of evidence studies for its closest read across substance with log Kow as the primary descriptor and on the basis of structural and functional similarity were reviewed for the toxicity on the invertebrates end point which are summarized as below:
In a prediction done by SSS (2017), Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the seven closest read across substances, toxicity on daphnia magna was predicted for 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8). Based on the immobility of test organism the EC50 value was estimated to be 0.133 mg/l when 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide exposed to daphnia magna for 48 hrs. Based on this value it can be concluded that the substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamideis considered to be toxic to aquatic environment and can classified as aquatic acute 1 as well as chronic 1 category as per the criteria mentioned in CLP regulation.
First predicted study was supported by the structurally and functionally similar read across chemical (103-90-2) from Environmental Toxicology and Chemistry 2006. Aim of the study was to assess the effect of chemical 4' Hydroxyacetanilidon (Acetaminophen) the growth of freshwater daphnia magna for the exposure period of 48 hrs. Testing was conducted according to the published Environment Canada biological test method. Test was conducted at 32, 10, 3.2, 1.0, and 0.1 ug/L, as well as a clean-water control. Chemical was analytically monitoring by HPLC and separation done by reverse-phase column using binary gradient elution at a constant temperature of 25°C. The neutral drugs were analyzed individually by full-scan MS in positive-ion mode, and quantitative analyses were performed using selective-ion monitoring mode. Dilutions of the stock sample solution were prepared in culture/dilution water and allowed to equilibrate. Portions of each concentration were then transferred to two glass beakers, one for testing and one for water-quality measurements. D. magna neonates younger than 24 hrs of age was used as a test organism. 10 daphnia magna were used in each test vessel. Water-quality measurements of each test vessel, including temperature, pH, and dissolved oxygen was measured after 48 hrs. Based on the immobility of daphnia magna due to the direct contact with the chemical 4' Hydroxyacetanilidon (Acetaminophen), the lethal concentration was > 0.032 mg/l. Thus based on the LC50, it can be concluded that the chemical was toxic and can be consider to be classified as aquatic acute 1 as well as chronic 1 category as per the CLP classification criteria.
Similarly in a supporting weight of evidence study for read across chemical (50-65-7) from ECOTOX database 2018 study was conducted. Study was conducted to determine the short term toxicity of 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (Niclosamide) to water flea daphnia magna. Test was conducted under the static system for the exposure period of 24 hrs. EC50 was measured on the basis of 50 % immobility of daphnia magna. Based on the immobility of freshwater water flea daphnia magna due to chemical 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (Niclosamide) for the total exposure period of 24 hrs, the EC50 was 0.16 mg/l. Thus based on the EC50 chemical was consider as toxic and can be consider to be classified as aquatic acute1/chronic 1 category as per the CLP classification criteria.
On the basis of above results for target chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8) (from OECD QSAR toolbox version 3.4) and for its read across substance from Environmental Toxicology and Chemistry 2006 and ECOTOX database it can be concluded that the test substance 2-[(E)-2-(4-chloro-2- nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (52320-66-8) is toxic and can be consider to be classified as aquatic acute1/chronic 1 category as per the CLP classification criteria.
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