Abstract
The complete environmental evaluation of any pesticide or other chemical involves consideration of the dosages applied, the movement and fate of residues of the compound and degradates in soil, water, air, plants, and animals, and the relationship of these residues with toxicity of living organisms. This review involves such an evaluation of dalapon (2,2-dichloropropionic acid) and its sodium and magnesium salts.
dalapon is the trademark of The Dow Chemical Company abroad, while “dalapon” is the common name approved by the British Standards Institute and the Weed Science Society of America.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Alabaster, J. S.: Survival of fish in 164 herbicides, insecticides, fungicides, wetting agents and miscellaneous substances. Internat. Pest. Control., pp. 29–35. Mar./Apr. (1969).
Alexander, H. C.: Toxicity of Dowpon S to three species of fish. Letter to G. E. Lynn, The Dow Chemical Company, Midland, Mich., Sept. 10 (1963).
-, and T. L. Batchelder: Biodegradability of DOWPON® M and dalapon herbicides. Report WCL 72004. Waste Control Laboratory, Dow Chemical USA, Midland, Mich. Dec. 4 (1972).
Anderson, L. D., and E. L. Atkins, Jr.: Toxicity of pesticides and other agricultural chemicals to honey bees. Proc. Reg. Pest. Chem. Applicators. Riverside, Calif. Apr. 3 and 4 (1967).
Anonymous: Code of Federal Regulations. 40. Protection of environment. Rev. Jan. 1, 1972. p. 425. Office of the Federal Register, National Archives and Records Service, General Services Administration, Washington, D.C. (1972).
Atkins, E. L., Jr., and L. D. Anderson: Toxicity of pesticides and other agricultural chemicals to honey bees. Laboratory studies. Circ. M. 16. Calif. Agr. Ext. Serv., Univ. of Calif. (1967).
Beall, M. L., P. C. Kearney, and D. D. Kaufman: Comparative metabolism of 1-14C- and 2-14C-labeled dalapon by soil microorganisms. Abstr. 1964 Meeting Weed Soc. Amer., p. 12 (1964).
Blanchard, F. A., W. W. Muelder, and G. N. Smith: Synthesis of carbon-14-labeled dalapon and trial applications to soybean and corn plants. J. Agr. Food Chem. 8, 124 (1960).
Bond, C. E., R. H. Lewis, and J. L. Fryer: Toxicity of various herbicidal materials to fishes. Trans. 1959 Seminar: Biological problems in water pollution, pp. 96–101. The Robert A. Taft Engineering Center, Tech. Rept. W60-3. Public Health Service, U.S.D.H.E.W., Cincinnati, Ohio (1960).
Bruns, V. F., and J. H. Dawson: Effects of DCB, DCB-xylene mixtures, Amitrol and sodium salt of dalapon in irrigation water on corn and rutabagas. Weeds 7, 333 (1959).
Brust, H.: Hydrolysis of dalapon sodium salt solutions. E. C. Britton Research Laboratory, The Dow Chemical Company, Midland, Mich., Nov. 11 (1953).
Bürge, W. D.: Populations of dalapon-decomposing bacteria in soil as influenced by additions of dalapon or other carbon sources. Applied Microbiol. 17, 545 (1969).
Butler, P. A.: Effects of herbicides on estuarine fauna. S. Weed Control Conf. Proc. 18, 57 (1965).
Corbin, F. T.: The influence of pH on the detoxification of herbicides in soil: Ph.D. thesis, N. Carolina St. Univ. Raleigh (1965).
Courtney, W. D., D. V. Peabody, and H. M. Austenson: Effect of herbicides on nematodes in bentgrass. Plant. Disease Reporter 42, 256 (1962).
Day, B. E., L. S. Jordan, and R. C. Russel: Persistence of dalapon residues in California soils. Soil Sci. 95, 326 (1963).
Dewitt, J. B.: Toxicity of pesticides to upland birds and wildfowl. Toxicity of dalapon (sodium 2,2-dichloropropionate). Work Unit D-1.7, Bureau of Sport Fisheries and Wildlife, U.S.D.L, Patuxent, Md. (1962).
Dillon, L. S.: The science of life, pp. 42–52. New York: MacMillan (1964).
Dunachte, J. F., and W. W. Fletcher: Effect of some herbicides on the hatching rate of hen’s eggs. Nature 215, 1406 (1967).
- - The toxicity of certain herbicides to hens eggs assessed by the egg injection technique. Ann. Applied Biol. 66, 515 (1970).
Duval, C. T.: Pesticides and the honey bee. PANS 15, 321 (1969).
Emerson, J. L., D. J. Thompson, and C. G. Gerbig: Results of teratological studies in rats treated orally with 2,2-dichloro-propionic acid (dalapon) during organogenesis. Rept. HH 417, Human Health Research and Development Laboratories, The Dow Chemical Company, Zionsville, Ind., Dec. 14 (1971).
Fertig, S. N., and M. M. Schreiber: Effect of dalapon ingestion on performance of dairy cattle and levels of residue in the milk. J. Agr. Food Chem. 9, 369 (1961).
Fox, C. J. S.: The effects of five herbicides on the numbers of certain invertebrate animals in grassland soil. Can. J. Plant Sci. 44, 405 (1964).
Foy, C. L.: Absorption, distribution and metabolism of 2,2-dichloropropionic acid in relation to phytotoxicity. II. Distribution and metabolic fate of dalapon in plants. PL Physiol. 36, 698 (1961).
- The chlorinated aliphatic acids. In P. C. Kearney and D. D. Kaufman (eds.): Degradation of herbicides, pp. 207–253. New York: Marcel Dekker (1969).
Frank, P. A., R. J. Demint, and R. D. Comes: Herbicides in irrigation water following canal-bank treatment for weed control. Weed Sci. 18, 687 (1970).
Gentry, W. M., and C. H. van Middelem: Determination of dalapon residues in grasses treated by DOWPON M herbicide for the control of smutgrass. Unpub. rept. GH-C 442, Agricultural Department, The Dow Chemical Company, Midland, Mich., Mar. 31 (1971).
Getzendaner, M. E.: Determination of residues of dalapon in asparagus, apples and pears. Unpub. rept. GH-C 113, Bioproducts Department, The Dow Chemical Company, Midland, Mich., May 6 (1964).
- Study of residues of dalapon in chicken tissues and eggs following repeated feeding. J. Agr. Food Chem. 16, 856 (1968).
- A study of residues in tissue of swine consuming dalapon. Unpub. rept. GH-C 338, The Dow Chemical Company, Midland, Mich. (1969 a).
- Study of residues in tissues from steers consuming dalapon. Unpub. rept. GH-C 339, The Dow Chemical Company, Midland, Mich. (1969 b).
- Residue study: Dalapon in grass treated with DOWPON M herbicide. Unpub. rept. GH-C 526, Agricultural Department, The Dow Chemical Company, Midland, Mich., Feb. 16 (1972).
Goldstein, H. E., and J. F. Long: Observations on cattle, sheep and swine exposed to 2,4-D, 2,4,5-T and dalapon herbicides. Presented S. Weed Control Conf., Biloxi, Miss., Jan. 20 (1960).
Hardy, J. L.: Eflect of DOWPON M on goldfish. Letter to F. Hoerger, The Dow Chemical Company, Midland, Mich., July 29, (1971).
Heath, R. G., J. W. Spann, E. F. Hill, and J. F. Kreitzer: Comparative dietary toxicities of pesticides to birds. Special Scientific Report–Wildlife No. 152, p. 28. Bureau of Sport Fisheries and Wildlife, U.S.D.I., Washington, D.C. (1972).
Helling, C. S.: Pesticide mobility in soils. II. Applications of soil thin-layer chromatography. Soil Sci. Soc. Amer. Proc. 35, 737 (1971).
Hiltibran, R. C.: Effects of some herbicides on fertilized fish eggs and fry. Trans. Amer. Fish Soc. 96, 414 (1967).
Hirsch, P., and M. Alexander: Microbial decomposition of halogenated propionic and acetic acids. Can. J. Microbiol. 6, 241 (1960).
Hoerger, F.: The metabolism of dalapon. Blood adsorption and urinary excretion patterns in dogs and human subjects. Unpub. rept., The Dow Chemical Company, Midland, Mich., July 31 (1969).
-, and E. E. Kenaga: Pesticide residues on plants: Correlation of representative data as a basis for estimation of their magnitude in the environment. Environ. Qual. and Safety, Vol. I. Stuttgart: Georg Thieme and New York: Academic Press (1972).
Holstun, J. T., Jr., and W. E. Loomis: Leaching and decomposition of 2,2-dichloropropionic acid in several Iowa soils. Weeds 4, 205 (1956).
Jensen, H. L.: Decomposition of choloro-substituted aliphatic acids by soil bacteria. Can. J. Microbiol. 3, 151 (1957).
Kaufman, D. D.: Microbial degradation of 2,2-dichloropropionic acid in five soils. Can. J. Microbiol. 10, 843 (1964).
Kearney, P. C., C. I. Harris, D. D. Kaufman, and T. J. Sheets: Behavior and fate of chlorinated aliphatic acids in soils. Adv. Pest. Control Res. 6, 1 (1965).
-, D. D. Kaufman, and M. L. Beall: Enzymatic dehalogenation of 2,2-dichlorpropionate. Biochem. Biophys., Res. Comm. 14(1), 29 (1964).
Kenaga, E. E.: The effect of dalapon on various species of aquatic animals. Unpublished letter rept., Agricultural Chemicals Research, The Dow Chemical Company, Midland, Mich., Oct. 14 (1968).
- Guidelines for evaluating the properties of pesticides for safe use in the wildlife environment. Down to Earth 23 (4), 11 (1968).
King, C. C.: Effects of herbicides on honeybees. Gleanings in Bee Culture, pp. 230–233 and 250–251, Apr. issue (1964).
Kutschinskl, A. H.: A laboratory method of determining the stability of dalapon sodium salt on soil and other media. Down to Earth 10 (3), 14 (1954).
-, Form and magnitude of 2,2-dichlorpropionic acid (dalapon) residues in milk. J. Agr. Food Chem. 9, 365 (1961).
Laskowski, D. A., and F. E. Broadbent: Effect of chlorinated aliphatic acids on gas and volatile fatty acid production in anaerobic soil. Soil Sci. Soc. Amer. Proc. 34, 72 (1970).
Lawrence, J. M.: Aquatic herbicide data. Agricultural Handbook No. 231, Agricultural Research Service, U.S. Department of Agriculture, Washington, D.C. (1962 a).
- Aquatic herbicide data, supplement I. Agricultural Experiment Station, Auburn Univ., Auburn, Ala., pp. 1–65 (1962 b).
Leasure, J. K.: The halogenated aliphatic acids. J. Agr. Food Chem. 12, 40 (1964).
Mackenzie, K. A., and I. C. Macrae: Tolerance of the nitrogen-fixing system of Azobacter vinelandii for four commonly used pesticides. Antonie van Leenmenhoek 38, 529 (1972).
Magee, L. A., and A. R. Colmer: Decomposition of 2,2-dichloropropionic acid by soil bacteria. Can. J. Microbiol. 5, 255 (1959).
Miller, P. W., and M. E. Getzendaner: Residues of dalapon in soil treated with DOWPON® Grass Killer. Unpub. rept. GH-C 658, The Dow Chemical Company, Midland, Mich., June 5 (1973).
Nelson, N. H., and S. D. Faust: Acidic dissociation constants of selected aquatic herbicides. Environ. Sci. Technol. 3, 1186 (1969).
Norris, J. M.: Acute toxicological properties of formulation M-3411 containing the sodium and magnesium salts of dalapon. Unpub. rept. BCT 2.30-45-4, Biochemical Research Laboratory, The Dow Chemical Company, Midland, Mich. Aug. 12 (1969 a).
- DOWPON M-606. Unpub. rept. BCT 2.30-45-4, Biochemical Research Laboratory, The Dow Chemical Company, Midland, Mich. Sept. 5 (1969 b).
Otten, R. J., J. E. Dawson, and M. M. Schreiber: The effects of several herbicides on nitrification in soil. Proc. NE Weed Control Conf. 11, 120 (1957).
Palmer, J. S., and R. D. Radeleff: The toxicity of some organic herbicides to cattle, sheep and chickens. ARS Production Research Report No. 106, pp. 1-3 and 23. U.S. Department of Agriculture (1969).
Paynter, O. E., T. W. Tusing, D. D. McCollister, and V. K. Rowe: Toxicology of dalapon sodium (2,2-dichloropropionic acid, sodium salt). J. Agr. Food Chem. 8,47 (1960).
Redemann, C. T., and J. W. Hamaker: The lactic secretion of metabolic products of ingested sodium 2,2-dichloropropionate by the dairy cow. Agricultural Research, The Dow Chemical Company, Seal Beach, Calif., July 14 (1959).
Reid, J. J.: Bacterial decomposition of herbicides. Proc. NE Weed Control Conf. 14, 19 (1960).
Sanders, H. O., and O. B. Cope: Toxicities of several pesticides to two species of cladocerans. Trans. Amer. Fisheries Soc. 95, 165 (1966).
- - The relative toxicities of several pesticides to naiads of three species of stoneflies. Limnology and Oceanography 13, 112 (1968).
Sandford, H., and F. R. Stovell: Residual phytotoxicity of amino triazole and dalapon to barley and kale. Proc. 5th Brit. Weed Control Conf., p. 321 (1960).
Sheets, T. J. and C I. Harris: Herbicide residues in soils and their phytotoxicities to crops grown in rotation. Residue Reviews 11, 119 (1965).
Smith, G. N., and D. L. Dyer: Fate of 2,2-dichloropropionic acid (dalapon) in the cotton plant. J. Agr. Food Chem. 9, 155 (1961).
-, M. E. Getzendaner, and A. H. Kutschinski: Determination of 2,2-dichloropropionic acid (dalapon) in sugar cane. J. Agr. Food Chem. 5, 675 (1957).
-, Y. S. Taylor, and B. S. Watson: Ecological studies on dalapon (2,2-dichloropropionic acid). Unpub. rept. NBE-16, Chemical Biology Research, The Dow Chemical Company, Midland, Mich., June 12 (1972).
Surber, E. W., and Q. H. Pickering: Acute toxicity of endothal, diquat, hyamine, dalapon and silvex to fish. The Progressive Fish-Culturist, pp. 164–171 (1962).
Svendsen, G. E.: Dalapon, sodium salt in acute toxicity studies. Mar. 11 letter to Ralph L. Gantz, The Dow Chemical Company. (1966).
Sweet, R. D., L. Feddema, G. Crabtree, and D. Bakes: Longevity of several herbicides in soils. Proc. NE Weed Control Conf. 12, 17 (1958).
Tacey, W. J., and R. R. Bellinger, Jr.: Hydrolysis of sodium 2,2-dichloropropionate in water solution. Midland Division, The Dow Chemical Company, Midland, Mich., Oct. 16 (1958).
Tanaka, F. S., and R. G. Wien: Hydrolysis of aqueous solutions of sodium 2,2-dichlorpropionate under self-induced alkaline conditions. Metabolism and Radiation Research Laboratory, A.R.S., U.S. Department of Agriculture. Fargo, N. Dak. (1972 a).
- - Photolysis of 2,2-dichloropropionic acid in aqueous solution. Metabolism and Radiation Research Laboratory, A.R.S., U.S. Department of Agriculture, Fargo, N. Dak. (1972 b).
The Dow Chemical Company: Unpublished data, several years.
Thiegs, B. J.: The stability of dalapon in soils. Down to Earth, Fall Issue (1955).
Thompson, D. J., C. G. Gerbig, and J. L. Emerson: Results of tolerance study of 2,2-dichloropropionic acid (dalapon) in pregnant rats. Unpub. rept. HH-393, Human Health Research and Development Center, The Dow Chemical Company, Zionsville, Ind., Sept. 29 (1971).
Tindle, R., D. Stalling, R. Hesselberg, and P. Benville: Comment in “Progress in sport fishery research 1969,” pp. 18–19. Resource pub. 88, Bureau of Sport Fisheries and Wildlife, U.S. Department of Interior, Washington, D.C. (1970).
U.S. Department of Interior: Pesticide-wildlife studies: A review of fish and wildlife service investigations during 1961 and 1962. Circ. 167, Fish and Wildlife Service, Washington, D.C., June (1963).
- Pesticide-wildlife studies, 1963. Circ. 199, Fish and Wildlife Service, Washington, D.C. (1964).
- effects of pesticides on fish and wildlife, 1964. Circ. 226, Fish and Wildlife Service, Washington, D.C., pp. 51–77 (1965).
Venkataraman, G. S., and B. Rajyalakshmi: Tolerance of bluegreen algae to pesticides. Current Sci. 40, 143 (1971).
Walsh, C. E.: Effects of herbicides on photosynthesis and growth of marine unicellular algae. Hyacinth Control J. 10, 45 (1972).
Warren, G. F.: Rate of leaching and breakdown of several herbicides in different soils. NC Weed Control Conf. Proc, 11th Ann. Meeting, Fargo, N. Dak. (1954).
Weed Science Society of America: Herbicide handbook, WSSA Monograph 3, 2d ed., pp. 180–183. Geneva, N.Y.: Humphrey Press (1970).
Winston, A. W., Jr.: Fish toxicity of dalapon and DOWPON. Letter rept. to G. E. Lynn, Waste Control Laboratory, The Dow Chemical Company, Midland, Mich., Sept. 18 (1964).
Worsham, A. D., and J. Giddens: Some effects of 2,2-dichloropropionic acid on soil microorganisms. Weeds 5, 316 (1957).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1974 Springer-Verlag New York Inc.
About this paper
Cite this paper
Kenaga, E.E. (1974). Toxicological and residue data useful in the environmental safety evaluation of dalapon. In: Gunther, F.A., Gunther, J.D. (eds) Residue Reviews. Residue Reviews, vol 53. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-9849-6_9
Download citation
DOI: https://doi.org/10.1007/978-1-4612-9849-6_9
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4612-9851-9
Online ISBN: 978-1-4612-9849-6
eBook Packages: Springer Book Archive