The potential of alkyl amines as antifouling biocides I: Toxicity and structure activity relationships

Biofouling

Volumn 9, Issue 4, 1996, Pages 257-268

  Finlay, J A ^a   Callow, Maureen E ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

algae; alkyl amines; antifouling paints; Artemia; biocides; biofouling

Indexed keywords

ALGAE; ARTEMIA;

EID: 0030485389     PISSN: 08927014     EISSN: None     Source Type: Journal    
DOI: 10.1080/08927019609378308     Document Type: Article

References (57)

1. Abel P D (1974) Toxicity of synthetic detergents to fish and aquatic invertebrates. J Fish Biol 6: 279-298
2. Alberte R S, Snyder S, Zahuranec B J, Whetstone M (1992) Biofouling research needs for the United States Navy: Program history and goals. Biofouling 6: 91-95
3. Callow M E (1986) Fouling algae from "in-service" ships. Bot Mar 24: 351-357
4. Callow M E, Finlay J A (1995) A simple method to evaluate the potential for degradation of antifouling biocides. Biofouling 9: 153-165
5. Christie A O, Crisp D J (1996) Toxicity of aliphatic amines to barnacle larvae. Comp Biochem Physiol 18: 59-69
6. Christie A O, Crisp D J (1967) Activity coefficients of the n-primary, secondary and tertiary aliphatic amines in aqueous solution. J Appl Chem 17: 11-14
7. Clifford D R, Cooke L, Davies S M (1976) The control in vitro of Ceratocystis ulmi by amine cations. Pestic Sci 7: 86-90
8. Dalley R (1989) Legislation affecting tributyltin antifoulings. Biofouling 1: 363-366
9. Daniel G F, Chamberlain A H L, Jones E B G (1987) Cytochemical and electron microscopical observations on the adhesive materials of marine fouling diatoms Br Phycol J 22: 101-118
10. Dave G, Blanck H, Gustafsson K (1979) Biological effects of solvent extraction chemicals on aquatic organisms. J Chem Technol Biotechnol 29: 249-257
11. Dave G, Anderson K, Berglind R, Hasselrot B (1981) Toxicity of eight solvent extraction chemicals and of cadmium to water fleas, Daphnia magna, Rainbow Trout, Salmo gairdneri, and Zebrafish, Brachydanto rerio. Comp Biochem Physiol 69: 83-98
12. Debye P (1949) Light scattering in soap solutions. J Phys Chem 53: 1-8
13. Denyer S P (1990) Mechanisms of action of biocides. Int Biodet 26: 89-100
14. Denyer S P, Hugo W B (1991) Biocide-induced damage to the bacterial cytoplasmic membrane. In: Denyer S P, Hugo W B (eds) Mechanisms of Action of Chemical Biocides, Their Study and Exploitation, The Society for Applied Bacteriology Technical Series No. 27, Blackwell Scientific Publications, Oxford, pp 171-187
15. Egan R R (1968) The preparation and properties of amines and cationic surfactants from fatty acids. J Am Oil Chem Soc 45: 481-486
16. Finlay J A (1995) Alkyl amines as antifouling biocides. PhD thesis, University of Birmingham.
17. Ford M G, Greenwood R, Turner C H, Hudson B and Livingstone D J (1989) The structure/activity relationships of pyrethroid insecticides. I. A novel approach based upon the use of multivariate QSAR and computational chemistry Pestic Sci 27: 305-326
18. Fujita T and Koga S (1966) The binding of a cationic detergent by yeast cells, in relation to its germicidal action. J Gen Appl Microbiol 12: 229-237
19. Gibson M T (1990) Developing biocidal compounds as freshwater algicides. Int Biodet 26: 149-158
20. Ginn M E, Kinney F B, Harris J C (1961) Effect of cotton substrate characteristics upon surfactant adsorption. J Am Oil Chem Soc 38: 138-143
21. Guillard R R L, Ryther J H (1962) Studies of marine planktonic diatoms. 1. Cyclotella nana Hustedt and Detonula confervacea (Cleve) Gran. Can J Microbiol 8: 229-239
22. Halsey G, Burkin A R (1962) Adsorption of long-chain aliphatic amines on glass vessels. Nature 193: 1177-1178
23. Hansch C, Glave W R (1975) Structure-activity relationships in membrane-perturbing agents. Hemolytic, narcotic and antibacterial compounds, Mol Pharmacol 7: 337-354
24. Harrington J C, Willingham G L (1993) An isothiazolone biocide for marine antifouling paints. Res Rev 43: 19-31
25. Hartley G S, Graham-Bryce I J (1980) Physical Principles of Pesticide Behaviour. Academic Press, London
26. Houghton D R (1984) Toxicity testing of candidate antifouling agents and accelerated antifouling paint testing. In: Costlow J B, Tipper R C (eds) Marine Biodeterioration: An Interdisciplinary Study. US Naval Research Institute, Annapolis MD, pp 255-260
27. Hueck H J, Adema D M M, Wiegmann J R (1966) Bacteriostatic, fungistatic, and algistatic activity of fatty nitrogen compounds. Appl Microbiol 14: 308-319
28. Hugo W B (1965) Some aspects of the action of cationic surface-active agents on microbial cells with special reference to their action on enzymes. In: Surface Activity and the Microbial Cell. Soc Chem Ind Monogr 19, pp 67-80
29. Hunter J E, Evans L V (1991) Raft trial experiments on antifouling paints containing zineb and copper. Biofoulding 3: 113-138
30. Isomaa B (1979) Interactions of surface-active alkyltrimethylammonium salts with the erythrocyte membrane. Biochem Pharmacol 28: 975-980
31. Isomaa B, Hagerstrand H, Paatero G, Engblom A C (1986) Permeability alterations and antihemolysis induced by amphiphiles in human erythrocytes. Biochim Biophys Acta 860: 510-524
32. Janczuk B, Chibowski E, Bialopiotrowicz T, Holysz L, Kliszcz A (1990) Influence of dodecylamine chloride on the surface free energy of kaolinite. Clays Clay Min 38: 53-56
33. Jarvis N L (1965) Surface viscosity of monomolecular films of long-chain aliphatic amides, amines, alcohols, and carboxylic acids. J Phys Chem 69: 1789-1797
34. 2 in higher plants, algae and natural phytoplankton. Biochem Physiol Pflanz (BPP) 167: 191-194
35. Kahan G J (1951) Hydrophobic films on solid surfaces. J Coll Sci 6. 571-575
36. Klein R A, Ellory J C (1980) Interaction of alkyl ammonium derivatives with red cells: haemolysis and sodium pump inhibition studies. J Memb Biol 55: 123-131
37. Langstone W J, Bryan G W, Burt G R, Gibbs P E (1990) Assessing the impact of tin and TBT in estuaries and coastal regions. Funct Ecol 4: 433-443
38. Leo A, Hansch C, Elkins D (1971) Partition coefficients and their uses. Chem Rev 71: 525-556
39. Linfield W M (1970) Straight-chain alkyl ammonium compounds. In: Jungerman E (ed) Cationic Surfactants. Marcel Dekker Incorporated, New York, pp 9-70
40. Livingstone D J (1989) Multivariate quantitative structure-activity relationship (QSAR) methods which may be applied to pesticide research. Pestic Sci 27: 287-304
41. MAFF (1995) Health, Safety Executive: Pesticides Approved under the Control of Pesticides Act 1986. Ministry of Agriculture Fisheries and Food. HMSO, London
42. Manahan S E (1988) Toxicological Chemistry. Lewis Publishers Incorporated. Chelsea, Michigan
43. McLachlan J (1960) The culture of Dunaliella tertiolecta Butcher - a euryhaline organism. Can J Microbiol 6: 367-379
44. Mukerjee P, Mysels K J (1971) Critical micelle concentrations of aqueous surfactant systems. In: National Standard Reference Data Systems. National Bureau of Standards, United States Department of Commerce, Washington, pp 1-180
45. Persoone G, Castritsi-Catharios J (1989) A simple bioassay with Artemia larvae to determine the acute toxicity of antifouling paints. Water Res 23: 893-897
46. nd Edn Henry Kimpton Publishers, London, pp 325-347
47. Rivett P (1965) Biological method for the assessment of leaching rates of antifouling compositions. J Appl Chem 15: 469-473
48. Roseman T J, Higuchi W I, Hodes B, Hefferren J J (1969) The retardation of enamel dissolution rates by adsorbed long-chain ammonium chlorides. J Dent Res 48: 509-520
49. nd Edn. John Wiley and Sons, Washington
50. Salerno M, Edgington L V (1963) Similarity of movement of N-alkyl quaternary ammonium compounds in aqueous systems on paper chromatograms and in plant xylem. Phytopathology 53: 605-607
51. Schwartz A M, Perry J W (1949) Surface Active Agents. Interscience Publishers Incorporated, New York
52. Schwuger M J, von Rybinski W, Krings P (1983) Adsorption of cationic surfactants on zeolite A. In: Ottewill R H, Rochester C H, Smith A L (eds) Adsorption from Solution at the Solid/Liquid Interface. Academic Press. London, pp 185-196
53. Seeman P (1972) The membrane actions of anesthetics and tranquilizers. Pharmacol Rev 24: 583-665
54. Void R D, Void M J (1983) Colloid and Interface Chemistry. Addison-Wesley Publishing Company Incorporated, Reading, Massachusetts
55. Weidhaas D E, Bowman M C, Schmidt C H (1961) Loss of parathion and DDT to soil from aqueous dispersions and vermiculite granules J Econ Entomol 54: 175-177
56. Weisman G R, Sundberg D C, Cimini R A, Brown M G, Beno D R, Eighmyn T T (1992) Controlled release antifouling coatings. I. Approaches for controlled release of 2,4-dinitrophenolate and benzoate into seawater. Biofouling 6: 123-146
57. White H J (1970) Absorption of cationic surfactants by cellulosic substrates. In: Jungerman E (ed) Cationic Surfactants Marcel Dekker Incorporated, New York, pp 311-340