2-nitro-p-anisidine

Short-term toxicity to aquatic invertebrates

Administrative data

Endpoint:

short-term toxicity to aquatic invertebrates

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Data source

Reference

Reference Type:

review article or handbook

Title:

Synthesis,electrochemistry,and molluscicidal activity of nitroaromatic compounds: effects of substituents and the role of redox potential

Author:

Abreu, Fabiane C. de et.al.

Year:

2011

Bibliographic source:

Reaxys by Elsevier Properties SA; Bioorganic & Medicinal Chemistry; vol.9(3);(2001);p.659

Materials and methods

Test guideline

Qualifier:

according to guideline

Guideline:

other:

Principles of method if other than guideline:

The compound was dissolved first in a small amount of DMSO and added to dechlorinated water, in order to have a solution of 0.1% in DMSO. The bioassay involved basically the immersion of the adult snail in the mixed aqueous solution of the compound under investigation at appropriate concentrations in order to verify the snails susceptibility.

GLP compliance:

not specified

Test material

Test material information

Constituent 1

Reference substance name:

2-nitro-p-anisidine

EC Number:

202-547-2

EC Name:

2-nitro-p-anisidine

Cas Number:

96-96-8

Molecular formula:

C7H8N2O3

IUPAC Name:

4-methoxy-2-nitroaniline

Details on test material:

98% from Aldrich

Test organisms

Test organisms (species):

other aquatic mollusc: Biomphalaria glabrata

Study design

Test type:

not specified

Water media type:

not specified

Total exposure duration:

1 wk

Results and discussion

Effect concentrations

Duration:

1 wk

Dose descriptor:

other: LD50

Effect conc.:

86.8 other: ppm

Nominal / measured:

meas. (not specified)

Conc. based on:

test mat.

Basis for effect:

mortality

Remarks on result:

other: presented a weak molluscicidal activity

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Conclusions:

The LD50 value of the substance is found to be 86.8 ppm.
The substance presented a weak molluscicidal activity.

Executive summary:

Molluscicidal bioassays and electrochemical studies (measurement of first wave reduction potential, Epc1) were performed on several synthetic nitroaromatics, in relation to possible correlation between biological activity, redox potential and structural effects. Five of them presented a significant molluscicidal activity onBiomphalaria glabrata (LD₅₀<20 ppm). The Epc1 values ranged from −0.532 to −0.857 V versus Ag/AgCl (0.1 M) (−0.260 to −0.585 V versus NHE), all of them, in the favorable range for reduction in vivo. Data comparison between Epc1 and molluscicidal activity indicates that the presence of the electroactive nitro group is important for the biological activity. Correlation with redox potential, however, was not evident. Structural effects seem to be the most important parameter. Higher activity is noticeable for phenols, including the para-nitro azo or hydrazo-containing compounds. No activity was observed for compounds having the benzylic substituent in meta position to the nitro group. These results suggest that activity undoubtedly involves more than reduction characteristics and that the possible formation of electrophilic species, after nitro reduction, can play an important role in molluscicidal activity against B. glabrata.