Aquatic ecotoxicity of a pheromonal antagonist in Daphnia magna and Desmodesmus subspicatus

Aquatic Toxicology

Volumn 79, Issue 3, 2006, Pages 296-303

  Rosa, Esmeralda ^a   Barata, Carlos ^b   Damásio, Joana ^b   Bosch, Ma Pilar ^a   Guerrero, Angel ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

Antagonist; Daphnia; Desmodesmus; Ecotoxicity; Pheromone; Sesamia nonagrioides; Trifluoromethyl ketones

Indexed keywords

11 HEXADECENYL ACETATE; 11 HEXADECENYL TRIFLUOROMETHYL KETONE; ACETIC ACID DERIVATIVE; CARBOXYLESTERASE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTAGONISM; AQUATIC ENVIRONMENT; BIOCONTROL AGENT; CRUSTACEAN; ECOTOXICOLOGY; ENZYME ACTIVITY; FEEDING BEHAVIOR; GREEN ALGA; GROWTH RATE; IMMOBILIZATION; INHIBITION; INSECT; MAIZE; ORGANIC COMPOUND; PHEROMONE;

ARTICLE; DAPHNIA; DESMODESMUS SUBSPICATUS; ECOTOXICITY; ENZYME ACTIVITY; FEEDING; GREEN ALGA; GROWTH INHIBITION; GROWTH RATE; IMMOBILIZATION; NONHUMAN; PRIORITY JOURNAL; SURVIVAL;

ACETATES; ACETYLCHOLINESTERASE; ACUTE TOXICITY TESTS; ALGAE, GREEN; ANIMALS; CARBOXYLESTERASE; DAPHNIA; DOSE-RESPONSE RELATIONSHIP, DRUG; ENVIRONMENTAL EXPOSURE; KETONES; LETHAL DOSE 50; SURVIVAL ANALYSIS; WATER POLLUTANTS, CHEMICAL;

MEDITERRANEAN REGION; MEDITERRANEAN SEA;

ALGAE; DAPHNIA; DAPHNIA MAGNA; DESMODESMUS; DESMODESMUS SUBSPICATUS; SESAMIA NONAGRIOIDES; ZEA MAYS;

EID: 33748787435     PISSN: 0166445X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.aquatox.2006.06.019     Document Type: Article

References (59)

1. Abdel-Aal Y.A.I., Roe R.M., and Hammock B.D. Kinetic properties of the inhibition of juvenile hormone esterase by two trifluoromethyl ketones and O-ethyl-S-phenylphosphoramidothiolate. Pest. Biochem. Physiol. 21 (1984) 232-241
2. Adelsbach T., and Tjeerdema R.S. Chemistry and fate of fenvalerate and esfenvalerate. Rev. Environ. Contam. Toxicol. 176 (2003) 137-154
3. Albajes R., Konstantopoulou M., Etchepare O., Eizaguirre M., Frérot B., Sans A., Krokos F., Améline A., and Mazomenos B. Mating disruption of the corn borer Sesamia nonagrioides (Lepidoptera: Noctuidae) using sprayable formulations of pheromone. Crop Prot. 21 (2002) 217-225
4. Allen Y., Calow P., and Baird D.J. A mechanistic model of contaminant-induced feeding inhibition in Daphnia magna. Environ. Toxicol. Chem. 14 (1995) 1625-1630
5. Ashour M.B.A., and Hammock B.D. Substituted trifluoromethylketones as potent, selective inhibitors of mammalian carboxylesterases. Biochem. Pharm. 36 (1987) 1869
6. Baird D.J., and Burton G.A. Ecological Variability: Separating Natural from Antropogeneic causes of Ecosystem Impairment (2001), SETAC Press, Brussels, Belgium
7. Barata C., and Baird D.J. Determining the ecotoxicological mode of action of chemicals from measurements made on individuals: results from instar-based tests with Daphnia magna Straus. Aquat. Toxicol. 48 (2000) 195-209
8. Barata C., Baird D.J., Miñarro A., and Soares A.M.V.M. Do genotype responses always converge from lethal to non-lethal toxicant exposure levels? A hypothesis tested using laboratory Daphnia magna Straus clones. Environ. Toxicol. Chem. 19 (2000) 2314-2322
9. Barata C., Porte C., and Baird D.J. Experimental designs to assess endocrine disrupting effects in invertebrates. A review. Ecotoxicology 13 (2004) 511-517
10. Barata C., Solayan A., and Porte C. Role of B-esterases in assessing toxicity of organophosphorous (chlorpyrifos, malathion) and carbamate (carbofuran) pesticides to Daphnia magna. Aquat. Toxicol. 66 (2004) 125-139
11. Bau J., Martinez D., Renou M., and Guerrero A. Pheromone-triggered orientation flight of male moths can be disrupted by trifluoromethyl ketones. Chem. Senses 24 (1999) 473-480
12. Cardé R.T., and Minks A.K. Control of moth pests by mating disruption. Annu. Rev. Entomol. 40 (1995) 559-585
13. Commission European Communities, 1993. Methods for determination of ecotoxicity. EEC Directive 92/69/EEC Annex V, C.3 Algal inhibition test. L 383A, Brussels, pp. 179-186.
14. Dabrowski J.M., and Schulz R. Predicted and measured levels of aziphosmethyl in the Lourens River, South Africa: comparison of runoff and spray drift. Environ. Toxicol. Chem. 22 (2003) 494-500
15. Day K.E., and Scott I.M. Use of acetylcholinesterase activity to detect sublethal toxicity in stream invertebrates exposed to low concentrations of organophosphate insecticides. Aquat. Toxicol. 18 (1990) 101-114
16. Dent D. Integrated insect pest management. In: Dent D. (Ed). Insect Pest Management (1993), CAB International, Wallingford 439-533
17. Dimitrov S.D., Mekenyan O.G., and Walker J.D. Non-linear modeling of bioconcentration using partition coefficients for narcotic chemicals. SAR QSAR Environ. Res. 13 (2002) 177-184
18. Durán I., Parrilla A., Feixas J., and Guerrero A. Inhibition of antennal esterases of the Egyptian armyworm Spodoptera littoralis by trifluoromethyl ketones. Bioorg. Med. Chem. Lett. 2 (1993) 243-252
19. Ellman G.L., Courtney K.D., Andres K.D., and Featherstone R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharm. 7 (1961) 88-95
20. Gelb M.H., Svaren J.P., and Abeles R.H. Fluoro ketone inhibitors of hydrolytic enzymes. Biochemistry 24 (1985) 1813-1817
21. Guerrero, A., Bosch, M.P., Rosell, G., Riba, M., Sans, A., 2003. Nuevas halometilcetonas y uso en la fabricación de trampas para el control biorracional de plagas de insectos. Patent 200301667, Spain, 13 pp.
22. Hammock B.D., Wing K.D., McLaughlin J., Lovell V.M., and Sparks T.C. Trifluoromethyl ketones as possible transition state analog inhibitors of juvenile hormone esterase. Pest. Biochem. Physiol. 17 (1982) 76-88
23. Jak R.G., Maas J.L., and Scholten M.C.T. Evaluation of laboratory derived toxic effect concentrations of a mixture of metals by testing freshwater plankton communities in enclosures. Water Res. 30 (1996) 1215-1227
24. Jokanovic M. Biotransformation of organophosphorus compounds. Toxicology 166 (2001) 139-160
25. Jonsson S., and Baun A. Toxicity of mono- and diesters of o-phthalic esters to a crustacean, a green alga, and a bacterium. Environ. Toxicol. Chem. 22 (2003) 3037-3043
26. Leslie H.A., Kraak M.H.S., and Hermens J.L.M. Chronic toxicity and body residues of the nonpolar narcotic 1,2,3,4-tetrachlorobenzene in Chironomus riparius. Environ. Toxicol. Chem. 23 (2004) 2022-2028
27. 19F NMR Spectral evidence that 3-octylthio-1,1,1-trifluoropropan-2-one, a potent inhibitor of insect juvenile hormone esterase, functions as a transition state analog inhibitor of acetylcholinesterase. Pest. Biochem. Physiol. 31 (1988) 187
28. Lowry O.H., Rosebrough N.J., Farr N.J., and Randall R.J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 93 (1951) 265-275
29. Marchini S., Passerini L., Hoglund M.D., Pino A., and Nendza M. Toxicity of aryl and benzyl halides to Daphnia magna and classification of their mode of action based on quantitative structure-activity relationships. Environ. Toxicol. Chem. 18 (1999) 2759-2766
30. Mastropaolo W., and Yourno J. An ultraviolet spectrophotometric assay for alpha-naphthyl butyrate esterases. Anal. Biochem. 115 (1981) 188-193
31. Meylan W.M., and Howard P.H. Atom, fragment contribution method for estimating octanol-water partition coefficients. J. Pharm. Sci. 84 (1995) 83-92
32. Muñoz L., Calvo T., Palerm A., Bosch D., Avilla J., Batllori L., Bosch M.P., Rosell G., and Guerrero A. Pheromonal perception inhibition of the leopard moth Zeuzera pyrina. Proceedings of the 22nd International Society of Chemical Ecology. Barcelona (2006) 66
33. Neuman M., Schulz R., Schäfer K., Müller W., Mannheller W., and Liess M. The significance of entry routes as point and non-point sources of pesticides in small streams. Water Res. 36 (2002) 835-842
34. OECD. Guidelines for Testing of Chemicals (1981), OECD, Paris
35. Papa E., Battaini F., and Gramatica P. Ranking of aquatic toxicity of esters modelled by QSAR. Chemosphere 58 (2005) 559-570
36. Pino A., Giuliani A., and Benigni R. Toxicity mode-of-action: discrimination via infrared spectra and eigenvalues of the modified adjacency matrix. QSAR Combust. Sci. 22 (2003) 191-195
37. Prestwich G.D. Chemical studies of pheromone reception and catabolism. In: Prestwich G.D., and Blomquist G.J. (Eds). Pheromone Biochemistry (1987), Academic Press, New York 473-527
38. Quero C., Bau J., Guerrero A., and Renou M. Responses of olfactory receptor neurons of the corn stalk borer Sesamia nonagrioides to components of the pheromone blend and their inhibition by trifluoromethyl ketone analogue of the main component. Pest. Manage. Sci. 60 (2004) 719-726
39. Renou M., Berthier A., Desbarats L., Van Der Pers J., and Guerrero A. Actographic analysis of the effects of an esterase inhibitor on male moth responses to sex pheromone. Chem. Senses 24 (1999) 423-428
40. Renou M., Berthier A., and Guerrero A. Disruption of responses to pheromone by (Z)-11-hexadecenyl trifluoromethyl ketone, an analogue of the pheromone, in the cabbage armyworm Mamestra brassicae. Pest Manage. Sci. 58 (2002) 839-844
41. Renou M., and Guerrero A. Insect parapheromones in olfaction research and semiochemical-based pest control strategies. Annu. Rev. Entomol. 48 (2000) 605-630
42. Reynolds C.S. Algae. In: Petts G., and Calow P. (Eds). River Biota. Diversity and Dynamics (1996), Blackwell Science, Oxford 6-26
43. Riba M., Sans A., Bau P., Grolleau G., Renou M., and Guerrero A. Pheromone response inhibitors of the corn stalk borer Sesamia nonagrioides. Biological evaluation and toxicology. J. Chem. Ecol. 27 (2001) 1879-1897
44. Riba M., Sans A., Solé J., Muñoz L., Bosch M.P., Rosell G., and Guerrero A. Antagonism of pheromone response of Ostrinia nubilalis males and implications on behavior in the laboratory and in the field. J. Agric. Food Chem. 53 (2005) 1158-1165
45. Rigol A., Latorre A., Lacorte S., and Barceló S. Determination of toxic compounds in paper-recycling process waters by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. J. Chromatogr. A 963 (2002) 265-275
46. Rosell G., Herrero S., and Guerrero A. New trifluoromethyl ketones as potent inhibitors of esterases: F -19 NMR spectroscopy of transition state analog complexes and structure-activity relationships. Biochem. Biophys. Res. Comm. 226 (1996) 287-292
47. Sans A., Solé J., Riba M., Barrot M., Palencia J., Castellà J., Rosa E., Bosch M.P., and Guerrero A. Mating disruption experiments of the Mediterranean corn borer Sesamia nonagrioides with a trifluoromethyl ketone analogue of the pheromone. Proceedings of the 22nd International Society Chemical Ecology Meeting. Barcelona (2006) 65
48. Staples C.A., and Davis J.W. An examination of the physical properties, fate, ecotoxicity and potencial environmental risks for series of propylene glycol ethers. Chemosphere 49 (2002) 61-73
49. Tatsuki S., and Kanno H. Disruption of sex pheromone communication in Chilo suppressalis with pheromones and analogues. In: Mitchell E.R. (Ed). Management of Insect Pests with Semiochemicals: Concepts and Practice (1981), Plenum Press, New York 313-325
50. Thompson D., Brunner J., Gut L., Judd G., and Knight A. Ten years implementing codling moth mating disruption in the orchards of Washington and British Columbia: starting right and managing for success. IOBC-WPRS Bull. 24 (2001) 23-30
51. van Leeuwen C.J., and Hermens J.L.M. Risk Assessment of Chemicals: An Introduction (1995), Kluwer Academic Press, London
52. van Leeuwen C.J., Van der Zandt P.T.J., Aldenberg T., Verhaar H.J.M., and Hermens J.L.M. Application of QSARs, extrapolation and equilibrium partitioning in aquatic effects assessment. I. Narcotic industrial pollutants. Environ. Toxicol. Chem. 11 (1992) 267-282
53. Verhaar H.J.M., Solbé J., Speksnijder J., van Leeuwen C.J., and Hermens J.L.M. Classifying environmental pollutants. Part 3. External validation of the classification system. Chemosphere 40 (2000) 875-883
54. Verhaar H.J.M., van Leeuwen C.J., and Hermens J.L.M. Classifying environmental pollutants. Part 1: Structure-activity relationships for prediction of aquatic toxicity. Chemosphere 25 (1992) 471-491
55. Vogt R.G., Riddiford L.M., and Prestwich G.D. Kinetic properties of a sex pheromone-degrading enzyme: the sensillar esterase of Antheraea polyphemus. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 8827-8831
56. Weatherston I., and Minks A.K. Regulation of semiochemicals-global aspects. Int. Pest Manage. Rev. 1 (1995) 1-13
57. Weininger D. SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci. 28 (1988) 31-36
58. Wheelock C.E., Colvin M.E., Uemura I., Olmstead M.M., Sanborn J.R., Nakagawa Y., Jones A.D., and Hammock B.D. Use of ab initio calculations to predict the biological potency of carboxylesterase inhibitors. J. Med. Chem. 45 (2002) 5576-5593
59. Zar J.H. Biostatistical Analysis (1996), Prentice-Hall International, Englewood Cliffs, NJ