Skip to main content
SpringerLink
Log in
Book cover

Residue Reviews pp 1–111Cite as

Metabolic fates of herbicides in animals

  • Conference paper

Part of the book series: Residue Reviews ((RECT,volume 58))

Abstract

The rapid increase in the worldwide production and usage of herbicides during the past three decades has been discussed and documented by Ashton and Crafts (1973) and others. The increased agricultural production made possible by these compounds continues to provide the economic stimulus to encourage the development and sale of new herbicides. Ashton and Crafts (1973) indicated that there are now more than 150 compounds that are currently being used as herbicides.

Mention of a trade name, proprietary product, or specific equipment does not constitute a guarantee or warranty by the U. S. Department of Agriculture and does not imply its approval to the exclusion of other products that may be suitable.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Adler, I. L., L. D. Haines, and J. P. Wargo, Jr.: Studies with dairy cows and laying hens fed alfalfa containing field-aged residues due to 3,5-dichloro-N-(l,l-dimethyl-2-propynyl)benzamide. J. Agr. Food Chem. 20, 1233 (1972).

    Article  CAS  Google Scholar 

  • Antognini, J., R. A. Gray, and J. J. Menn: Chemical, physical, topological, and biochemical properties of cycloate. Proc. Selective Weed Control in Beet Crops, 2nd Internat. 1, 293 (1970).

    Google Scholar 

  • Aschbacher, P .W., and V. J. FeIl: Metabolism of 3,5-diiodosalicylic acid in cattle and rats. J. Dairy Sci. 51, 762 (1968).

    Article  CAS  Google Scholar 

  • Ashton, F. M., and A. S. Crafts: Mode of action of herbicides. New York: Wiley Interscience (1973).

    Google Scholar 

  • Bache, C. A., D. D. Hardee, R. F. Holland, and D. J. Lisk: Absence of phenoxy-acid herbicide residues in the milk of dairy cows at high feeding levels. J. Dairy Sci. 47,298 (1964 a).

    Article  CAS  Google Scholar 

  • Bache, C. A., D. D. Hardee, R. F. Holland, D. J. Lisk, D. G. Wagner, and R. G. Warner: Elimination of 2-methyl-4-chlorophenoxyacetic acid and 4-(2-methyl-4-ehlorophenoxybutyric) acid in the urine from cows. J. Dairy Sci. 47, 93 (1964 b).

    Article  CAS  Google Scholar 

  • Bakke, J. E., and C. E. Price: Rat urinary metabolites from 2-methoxy-4,6-bis-(isopropylamino)-s-triazine (Prometone). J. Agr. Food Chem. 21, 640 (1973).

    Article  CAS  Google Scholar 

  • Bakke, J. E., C. E. Price, J. D. Larson, and C. E. Price: Metabolism of atrazine and 2-hydroxyatrazine by the rat. J. Agr. Food Chem. 20, 602 (1972).

    Article  CAS  Google Scholar 

  • Bakke, J. E., C. E. Price, J. D. Robbins, and V. J. Feil: Metabolism of 2-chloro-4,6-bis(isopropylamino)-5-triazine (propazine) and 2-methoxy-4,6-bis(isopropylamino)-5-triazine (prometone) in the rat. Balance study and urinary metabolite separation. J. Agr. Food Chem. 15, 628 (1967).

    Article  CAS  Google Scholar 

  • Bakke, J. E., and C. E. Price, J. D. Robbins, and V. J. Feil: Metabolism of 2-methoxy-4-ethylamino-6-sec-butylamino-s-triazine by the dairy cow and the goat. J. Agr. Food Chem. 19, 462 (1971).

    Article  CAS  Google Scholar 

  • Balayannis, P. G., M. S. Smith, and R. L. Wain: Studies on plant growth-regulating substances. XIX. Stability of 2,3,6-trichlorobenzoic acid in wheat plants and in the rabbit and mouse. Ann. Applied Biol. 55, 149 (1965).

    Article  CAS  Google Scholar 

  • Bandal, S. K., and J. E. Casida: Metabolism and photoalteration of 2-sec-butyl-4,6-dinitrophenol (DNBP herbicide) and its isopropyl carbonate derivative (dino-buton acaricide). J. Agr. Food Chem. 20, 1235 (1972).

    Article  CAS  Google Scholar 

  • Barker, W. M., P. L. Moy, and A. G. Ebert: Distribution and metabolism of carboxyl-14C-2,3,5-triiodobenzoic acid and 2,3(125I)-triiodobenzoic acid in the rat. J. Agr. Food Chem. 19, 916 (1971).

    Article  CAS  Google Scholar 

  • Belasco, I. J., and R. W. Reiser: Metabolic fate of siduron in the animal. J. Agr. Food Chem. 17, 1000 (1969).

    Article  CAS  Google Scholar 

  • Bend, J. R., G. M. Holder, and A. J. Ryan: Further studies on the metabolism of isopropyl N-phenylcarbamate (propham) in the rat. Food Cosmet. Toxicol. 9, 169 (1971).

    Article  PubMed  CAS  Google Scholar 

  • Berndt, W. O., and F. Koschter: In vitro uptake of 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) by renal cortical tissue of rabbits and rats. Toxicol. Applied Pharmacol. 26, 559 (1973).

    Article  CAS  Google Scholar 

  • Black, W. J. M., A. Calderbank, G. Douglas, and R. H. McKenna: Residues in herbage and silage and feeding experiments following the use of diquat as a desiccant. J. Sci. Food Agr. 17, 506 (1966).

    Article  CAS  Google Scholar 

  • Blinn, R. C: Biochemical behavior of 2-chloroethyl trimethylammonium chloride in wheat and in rats. J. Agr. Food Chem. 15, 984 (1967).

    Article  CAS  Google Scholar 

  • Bobik, A., G. M. Holder, and A. J. Ryan: Excretory and metabolic studies of CIPC (isopropyl IV-(3-chlorophenyl)carbamate) in the rat. Food Cosmet. Toxicol. 10, 163(1972).

    Article  PubMed  CAS  Google Scholar 

  • Bohme, C., and F. Bar: Über den Abbau von Triazin-Herbiciden im tierischen Organismus. Food Cosmet. Toxicol. 5, 23 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Bohme, C., F. Bar, and W. Ernst: Über den Stoffwechsel von Harnstoffherbiciden in der Ratte. 2. Mitteilung. Diuron und Afalon. Food Cosmet. Toxicol. 3, 797 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Bough, R. G., E. E. Cliffe, and B. Lessel: Comparative toxicity and blood level studies on binapacryl and DNBP. Toxicol. Applied Pharmacol. 7, 353 (1965).

    Article  CAS  Google Scholar 

  • Boyd, V. F., and R. W. Fogleman: Metabolism of fluometuron (l,l-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea) in the rat. 153rd Meeting Amer. Chem. Soc., Miami, Apr., A-42 (1967).

    Google Scholar 

  • Bray, H. G., S. P. James, W. V. Thorpe, and M. R. Wasdell: The metabolism of ethers in the rabbit. 1. Anisole and diphenyl ether. Biochem. J. 54, 547 (1953).

    PubMed  CAS  Google Scholar 

  • Calderbank, A., R. H. McKenna, M. A. Stevens, and J. K. Walley: Grazing trials on paraquat-treated pasture. J. Sci. Food Agr. 19, 246 (1968).

    Article  Google Scholar 

  • Chasseaud, L. F., D. R. Hawkins, B. D. Cameron, B. J. Fry, and V. H. Saggers: The metabolic fate of bentazon in the rat. Xenobiotica 2, 269 (1972).

    Article  PubMed  CAS  Google Scholar 

  • Clark, D. E., and J. S. Palmer: Residual aspects of 2,4,5-T and an ester in sheep and cattle with observations on concomitant toxicological effects. J. Agr. Food Chem. 19,761 (1971).

    Article  CAS  Google Scholar 

  • Clark, D. E., and J. S. Palmer, J. E. Young, R. L. Younger, L. M. Hunt, and J. K. McLaran: The fate of 2,4-dichlorophenoxyacetic acid in sheep. J. Agr. Food Chem. 12, 43 (1964).

    Article  CAS  Google Scholar 

  • Clark, D. G.: Inhibition of the absorption of paraquat from the gastrointestinal tract by adsorbents. Brit. J. Ind. Med. 28, 186 (1971).

    CAS  Google Scholar 

  • Conning, D. M., K. Fletcher, and A. A. B. Swan: Paraquat and related bipyridyls. Brit. Med. Bull. 25, 245 (1969).

    PubMed  CAS  Google Scholar 

  • Crayford, J. V., and D. H. Hutson: The metabolism of the herbicide, 2-chloro-4-(ethylamino)-6-(l-cyano-l-methylethylamino)-s-triazine in the rat. Pest. Biochem. Physiol. 2, 295 (1972).

    Article  CAS  Google Scholar 

  • Daniel, J. W., and J. C. Gage: Absorption and excretion of diquat and paraquat in rats. Brit. J. Ind. Med. 23, 133 (1966).

    CAS  Google Scholar 

  • Dupuis, G., T. Laanio, P. Marbach, and H. O. Esser: Degradation in corn, alfalfa, soil and in the rat of metabolites common to various triazine herbicides. 7th Internat. Congress Plant Prot, Paris, Sept. 21–25, p. 711 (1970).

    Google Scholar 

  • Emmerson, J. L., and R. C. Anderson: Metabolism of trifluralin in the rat and dog. Toxicol. Applied Pharmacol. 9, 84 (1966).

    Article  CAS  Google Scholar 

  • Erne, K.: Distribution and elimination of chlorinated phenoxyacetic acids in animals.Acta Vet. Scand. 7, 240 (1966)

    PubMed  CAS  Google Scholar 

  • Erne, K.: Studies on the animal metabolism of phenoxyacetic herbicides. Acta Vet. Scand. 7,264 (1966 b).

    PubMed  CAS  Google Scholar 

  • Ernst, V. W. and F. Bar: Die Umwandlung des 2,4-Dinitro-6-sec-butylphenols und seiner Ester im tierischen Organisms. Arzneimittel Forsch. 14, 81 (1964).

    CAS  Google Scholar 

  • Ernst, W. and C. Bohme: Über den Stoffwechsel von Harnstoffherbiciden in der Ratte. 1. Mitteilung. Monuron und Aresin. Food Cosmet. Toxicol. 3, 789 (1965).

    CAS  Google Scholar 

  • Fang, S. C., M. George, and V. H. Freed: The metabolism of S-propyl-1-C14 n-butylethylthiocarbamate (Tillam-C14) in rats. J. Agr. Food Chem. 12, 37 (1964 a).

    Article  CAS  Google Scholar 

  • Fang, S. C., M. George, V. H. Freed, and T. C. Yu: Metabolism of 3-amino-l,2,4-triazole-5-C14 by rats. J. Agr. Food Chem. 12, 219 (1964 b).

    Article  CAS  Google Scholar 

  • Fang, S. C., M. George, V. H. Freed, S. Khanna, and A. V. Rao: Further study on the metabolism of labeled 3-amino-l,2,4-triazole (ATA) and its plant metabolites in rats. J. Agr. Food Chem. 14,262 (1966).

    Article  CAS  Google Scholar 

  • Fisher, D. E., L. E. St. John, Jr., W. H. Gutenmann, D. G. Wagner, and D. J. Lisk: Fate of Banvel T, ioxynil, tordon, and trifluralin in the dairy cow. J. Dairy Sci. 48,1711 (1965).

    Article  CAS  Google Scholar 

  • Frear, D. E. H.: Pesticide handbook, 20th ed. State College, Pa.: College Science Publishers (1968).

    Google Scholar 

  • Fridman, E. B.: Distribution and accumulation of monuron in animals and methods of its excretion. Zdravookjr Turhm. 12, 25 (1968).

    Google Scholar 

  • FröslIe, A. and O. Karlog: Ruminal metabolism of DNOC and DNBP. Acta Vet. Scand. 11,114 (1970).

    PubMed  Google Scholar 

  • Gardiner, J. A., R. W. Reiser, and H. Sherman: Identification of the metabolites of bromacil in rat urine. J. Agr. Food Chem. 17, 967 (1969 a).

    Article  CAS  Google Scholar 

  • Gardiner, J. A., R. W. Reiser, H. Sherman, R. C. Rhodes, J. B. Adams, Jr., and E. J. Soboczenski: Synthesis and studies with 2-C14-labeled bromacil and terbacil. J. Agr. Food Chem. 17, 980 (1969 b).

    Article  CAS  Google Scholar 

  • Gehring, P. J., C. G. Kramer, B. A. Schwetz, J. Q. Rose, and V. K. Rowe: The fate of 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) following oral administration to man. Toxicol. Applied Pharmacol. 26, 352 (1973).

    Article  CAS  Google Scholar 

  • Geldmacher, M., V. Mallinckrodt, and H. P. Schmidt: Zur Toxizität und Stoff-wechsel von Aminotriazol beim Menschen. Arch. Toxikol, 27, 13 (1970).

    Article  Google Scholar 

  • Geldmacher, M., V. Mallinckrodt, and H. P. Schmidt, and F. Schüssler: Zu Stoffwechsel und Toxizität von l-(3,4-Dichloro-phenyl)-3,3-dimethylharnstoff (Diuron) beim Menschen. Arch. Toxikol. 27, 187 (1971).

    Article  Google Scholar 

  • Getzendaner, M. E.: Study of residues of dalapon in chicken tissues and eggs following repeated feeding. J. Agr. Food Chem. 16, 856 (1968).

    Article  CAS  Google Scholar 

  • Grbson, J. E., and K. S. Rao: Disposition of 2-seobutyl-4,6-dinitrophenol (dinoseb) in pregnant mice. Food Cosmet. Toxicol. 11, 45 (1973).

    Article  Google Scholar 

  • Golab, T., R. J. Herberg, E. W. Day, A. P. Raun, F. J. Holzer, and G. W. Probst: Fate of carbon-14 trifluralin in artificial rumen fluid and in ruminant animals. J. Agr. Food Chem. 17, 576 (1969).

    Article  CAS  Google Scholar 

  • Golab, T., R. J. Herberg, E. W. Day, J. V. Gramlich, A. P. Raun, and G. W. Probst: Fate of benefin in soils, plants, artificial rumen fluid, and the ruminant animal. J. Agr. Food Chem. 18,838 (1970).

    Article  CAS  Google Scholar 

  • Griffiths, M. H., J. A. Moss, J. A. Rose, and D. E. Hathway: The comparative metabolism of 2,6-dichlorothiobenzamide (prefix) and 2,6-dichlorobenzonitrile in dog and rat. Biochem. J. 98, 770 (1966).

    PubMed  CAS  Google Scholar 

  • Grunow, W., C. Bohme, and B. Budczies: The metabolism of carbamate herbicides in the rat. 2. Metabolism of chlorpropham and barban. Food Cosmet. Toxicol. 8, 277 (1970).

    CAS  Google Scholar 

  • Grunow, W., C. Bohme, and B. Budczies: Renale Ausscheidung von 2,4,5-T bei Ratten. Food Cosmet. Toxicol. 9,667 (1971).

    Article  PubMed  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, and D. J. Lisk: Fate of the plant regulator 2,3,5-triiodobenzoic acid (TIBA) in the bovine. J. Agr. Food Chem. 15, 600 (1967).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Disappearance of 4-(2,4-dichlorophenoxybutyric) acid herbicide in the dairy cow. J. Dairy Sci. 46, 991 (1963 a).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Residue studies with 2,4-dichlorophenoxyacetic acid herbicide in the dairy cow and in a natural and artificial rumen. J. Dairy Sci. 46, 1287 (1963 b).

    Article  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Conversion of 4-(2,4-DB) herbicide to 2,4-D by bluegills. N. Y. Fish and Game J. 12, 108 (1965).

    Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Metabolism of Daconil and Dacthal pesticides in lactating cows. J. Dairy Sci. 49,1272 (1966).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Metabolism of TOK herbicide in the dairy cow. J. Dairy Sci. 50, 1516 (1967).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Excretory pathway of terbacil (sinbar) in lactating cows. J. Agr. Food Chem. 17,1011 (1969).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Metabolism and excretion of bromacil in milk of dairy cows. J. Agr. Food Chem. 18, 128 (1970 a).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Metabolism of planavin herbicide in a lactating cow. J. Dairy Sci. 53, 1289 (1970 b).

    Article  PubMed  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, and D. J. Lisk: Metabolic studies with Bexide (herbisan) herbicide in the dairy cow. J. Agr. Food Chem. 19, 200 (1971).

    Article  CAS  Google Scholar 

  • Gutenmann, W. H., C. A. Bache, D. D. Hardee, R. F. Holland, J. W. Serum, and D. J. Lisk: Feeding studies with VCS-438 herbicide in the dairy cow. J. Agr. Food Chem. 20, 991 (1972).

    Article  CAS  Google Scholar 

  • Hapke, H. J.: Untersuchungen zur Toxikologie des Unkrautverniehters Simazin. Berlin Muenchen Tieraerzil Wochenschr. 81, 301 (1968).

    CAS  Google Scholar 

  • Harvey, D. G.: Some aspects of the metabolism of 4:6-dinitro-o-cresol (DNC) by the ruminant. J. Comp. Pathol. 68, 54 (1958).

    PubMed  CAS  Google Scholar 

  • Harvey, D. G.: Resorption of DNBP (4,6-dmitro-2-sec-butylphenol) and DNPP (4,6,dinitro-2-isopropylphenol) through the skin of rats. Acta Polon. Pharmaceut. 23, 371 (1966).

    Google Scholar 

  • Henneberg, M.: Metabolites of dinitroisopropylphenol (DNPP) and of dinitro-butylphenol (DNBP) in the rat’s organism. Acta Polon. Pharm. 21, 236 (1964).

    Google Scholar 

  • Hodge, H. C, W. L. Downs, D. W. Smith, E. A. Maynard, J. W. Clayton, Jr., and H. L. Pease: Oral toxicity of linuron [3-(3,4-dicHorophenyl)-l-methoxy-1-methylurea] in rats and dogs. Food Cosmet. Toxicol. 6, 171 (1967).

    Article  Google Scholar 

  • Holder, G. M. and A. J. Ryan: Metabolism of propham’ (isopropyl N-phenyl-carbamate) in the rat. Nature 220, 77 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Hutson, D. H., E. C. Hoadley, M. H. Griffiths, and C. Donninger: Mercapturic acid formation in the metabolism of 2-chloro-4-ethylamino-6-(1-methyl-l-cyano-ethylamino)-s-triazine in the rat. J. Agr. Food Chem. 18, 507 (1970).

    Article  CAS  Google Scholar 

  • Ice, R. D., C. E. Breckinridge, Jr., and J. E. Christian: Retention, excretion, and distribution of 2,3,5-triiodobenzoic acid and its metabolites in the rat. J. Pharm. Sci. 55,497 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Ice, R. D., C. E. Breckinridge, Jr., J. E. Christian, and M. P. Plumlee: Metabolic fate of orally administered 2,3,5-triiodobenzoic acid in lactating animals. J. Pharm. Sci. 57, 399 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Ishikawa, K., I. Okuda, and S. Kuwatsuka: Metabolism of benthiocarb (4-chloro-benzyl IV,IV-diethylthiocarbamate) in mice. Agr. Biol. Chem. 37, 165 (1973).

    Article  CAS  Google Scholar 

  • Jakobson, I., and S. Yllner: Metabolism of 14C-pentachlorophenol in the mouse. Acta Pharmacol, et Toxicol. 29, 513 (1971).

    Article  CAS  Google Scholar 

  • Jegatheeswaran, T. and D. G. Harvey: The metabolism of DNOC in sheep. Vet. Rec. 87, 19 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Kearney, P. C. and D. D. Kaufman: Degradation of herbicides. New York: Marcel Dekker (1969).

    Google Scholar 

  • Khanna, S. and S. C. Fang: Metabolism of C14-labeled 2,4-dichlorophenoxyacetic acid in rats. J. Agr. Food Chem. 14, 500 (1966).

    Article  CAS  Google Scholar 

  • Khokholkova, G. A., and A. G. Pestova: Accumulation and distribution of Diptal (trichloroallyl diisopropylthiocarbamate) in rats following ingestion. Vrach. Delo 5,99 (1969).

    CAS  Google Scholar 

  • King, E. and D. G. Harvey: On the metabolism of some aromatic nitro compounds by different species of animal. Part 1. Some factors influencing the elimination of 4:6-dinitro-o-cresol from the blood of the rat. J. Pharm. Pharmacol. 6, 529 (1954).

    Article  PubMed  CAS  Google Scholar 

  • King, E. and D. G. Harvey: Some observations on the absorption and excretion of 4:6-dinitro-o-cresol (DNOC). 1. Blood dinitro-o-cresol levels in the rat and the rabbit following different methods of absorption. Biochem. J. 53, 185 (1953 a).

    PubMed  CAS  Google Scholar 

  • King, E. and D. G. Harvey: Some observations on the absorption and excretion of 4:6-dinitro-o-cresol. 2. The elimination of 4:6-dinitro-o-cresol by man and by animals. Biochem. J. 53, 196 (1953 b).

    PubMed  CAS  Google Scholar 

  • Kjnoshita, F. K., and K. P. Dubois: Induction of hepatic microsomal enzymes by herban, diuron, and other substituted urea herbicides. Toxicol. Applied Pharmacol. 17, 406 (1970).

    Article  Google Scholar 

  • Klingman, D. L., C. H. Gordon, G. Yep, and H. P. Burchfield: Residues in the forage and in milk from cows grazing forage treated with esters of 2,4-D. Weeds 14,164 (1966).

    Article  CAS  Google Scholar 

  • Knaak, J. B. and L. J. Sullivan: Metabolism of 3,4-dichlorobenzyl N-methylcarba-mate in the rat. J. Agr. Food Chem. 16, 454 (1968).

    Article  CAS  Google Scholar 

  • Kutschinski, A. H.: Form and magnitude of 2,2-dichloropropionic acid (dalapon) residues in milk. J. Agr. Food Chem. 9, 365 (1961).

    Article  CAS  Google Scholar 

  • Kutschinski, A. H.: Residues in milk from cows fed 4-amino-3,5,6-trichloropicolinic acid. J. Agr. Food Chem. 17, 288 (1969).

    Article  CAS  Google Scholar 

  • Kutschinski, A. H. and van Riley: Residues in various tissues of steers fed 4-aniino-3,5,6-trichloro-pieolinic acid. J. Agr. Food Chem. 17, 283 (1969).

    Article  CAS  Google Scholar 

  • Larson, J. D. and J. E. Bakke: Metabolism of plant metabolites of s-triazine herbicides in the rat. Proc. N. Dak. Acad. Sci. 24, 178 (1971).

    CAS  Google Scholar 

  • Leasure, J. K.: Metabolism of herbicides: The halogenated aliphatic acids. J. Agr. Food Chem. 12, 40 (1964).

    Article  CAS  Google Scholar 

  • Lisk, D. J., W. H. Gutenmann, C. A. Bache, R. G. Warner, and D. G. Wagner: Elimination of 2,4-D in the urine of steers fed 4-(2,4-DB) or 2,4-D. J. Dairy Sci. 46,1435 (1963).

    Article  CAS  Google Scholar 

  • Marshall, F. J., R. E. McMahon, and R. G. Jones: Preparation and stability of C14-labeled trifluralin and related compounds. J. Agr. Food Chem. 14, 498 (1966).

    Article  CAS  Google Scholar 

  • Martin, H.: Pesticide manual, 2nd ed. British Crop Protection Council (1971).

    Google Scholar 

  • Matlib, M. A., R. C. Kirkwood, and J. D. E. Patterson: Binding of certain substituted phenoxy-acids by bovine serum albumin. Weed Res. 11, 190 (1971).

    Article  CAS  Google Scholar 

  • McGahen, J. W., and C. E. Hoffmann: Action of 5-bromo-3-sec-butyl-6-methyl-uracil on Escherichia coli 15 T. Nature 200, 571 (1963 a).

    Article  PubMed  CAS  Google Scholar 

  • McGahen, J. W., and C. E. Hoffmann: Action of 5-bromo-3-sec-butyl-6-methyluracil as regards replacement of thymine in mouse DNA. Nature 199, 810 (1963 b).

    Article  PubMed  CAS  Google Scholar 

  • McGee, C. E., G. S. Born, J. E. Christian, and B. J. Liska: Metabolites of 2,3,5-triiodobenzoic acid in cow’s milk. J. Dairy Sci. 52, 1864 (1969).

    Article  PubMed  CAS  Google Scholar 

  • McKellar, R. L.: 2-Sec-butyl-4,6-dinitrophenol and 2-amino-6-sec-butyl-4-nitro-phenol in milk and cream from cows fed 2-sec-butyl-4,6-dinitrophenol. J. Agr. Food Chem. 19, 758 (1971).

    Article  CAS  Google Scholar 

  • McMahon, R. E. and H. R. Sullivan: The metabolism of the herbicide diphenamid in rats. Biochem. Pharmacol. 14, 1085 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Menzer, R. E.: Biological oxidation and conjugation of pesticidal chemicals. Residue Reviews 48, 79 (1973).

    PubMed  CAS  Google Scholar 

  • Mitchell, J. W., R. E. Hodgson, and C. F. Gaetjens: Tolerance of farm animals to feed containing 2,4-dichlorophenoxyacetic acid. J. Animal Sci. 5, 226 (1946).

    CAS  Google Scholar 

  • Oliver, W. H., G. S. Born, and P. L. Ziemer: Retention, distribution, and excretion of ametryne (2-methylmercapto-4-ethylamino-6-isopropylamino-5-triazine) in the rat. J. Agr. Food Chem. 17, 1207 (1969).

    Article  CAS  Google Scholar 

  • Ong, V. Y. and S. C. Fang: In vivo metabolism of ethyl-l-14C-N,IV-di-n-propyl-thiolcarbamate in rats. Toxicol. Applied Pharmacol. 17, 418 (1970).

    Article  CAS  Google Scholar 

  • Parker, V. H., J. M. Barnes, and F. A. Denz: Some observations on the toxic properties of 3:5-dinitro-ortho-cresol. Brit. J. Ind. Med. 8, 226 (1951).

    CAS  Google Scholar 

  • Paulson, G. D., M. M. Dockter, A. M. Jacobsen, and R. G. Zaylskie: Isopropyl carbanilate (propham) metabolism in the chicken: Balance studies and isolation and identification of excreted metabolites. J. Agr. Food Chem. 20, 867 (1972 a).

    Article  CAS  Google Scholar 

  • Paulson, G. D., M. M. Dockter, and A. M. Jacobsen: Isolation and identification of propham (isopropyl carbanilate) metabolites from animal tissues and milk. J. Agr. Food Chem. 22, 629 (1974).

    Article  CAS  Google Scholar 

  • Paulson, G. D., M. M. Dockter, and M. V. Zehr: Metabolism of p-chlorophenyl N-methylcarbamate in the chicken. J. Agr. Food Chem. 19, 471 (1971).

    Article  CAS  Google Scholar 

  • Paulson, G. D., M. M. Dockter, A. M. Jacobsen, and R. G. Zaylskie: Metabolism of the herbicide N-(tri-fluoromethylsulfono)-2-methyl-4-(phenylsulfono)-aniline in the rat. 166th Amer. Chem. Soc. Meeting, Pest. Chem. Div., Abstr. 17, Chicago (1973 a).

    Google Scholar 

  • Paulson, G. D., M. M. Dockter, A. M., Jacobsen, R. G. Zaylskie, and V. J. Feil: Isolation and identification of propham (isopropyl carbanilate) metabolites from the rat and the goat. J. Agr. Food Chem. 21, 804 (1973 b).

    Article  CAS  Google Scholar 

  • Paulson, G. D., M. M. Dockter, and R. G. Zaylskie: Metabolism of p-chlorophenyl N-methylcarbamate in the rat and goat. J. Agr. Food Chem. 20, 33 (1972 b).

    Article  CAS  Google Scholar 

  • Paynter, O. E., T. W. Tusing, D. D. McCollister, and V. K. Rowe: Toxicity of dalapon sodium (2,2-dichloropropionic acid, sodium salt). J. Agr. Food Chem. 8,47 (1960).

    Article  CAS  Google Scholar 

  • Piper, W. N., J. Q. Rose, M. L. Leng, and P. J. Gehring: The fate of 2,4,5-tri-chlorophenoxyacetic acid (2,4,5-T) following oral administration to rats and dogs. Toxicol. Applied Pharmacol. 26, 339 (1973).

    Article  CAS  Google Scholar 

  • Pirie, A. and J. R. Rees: Diquat cataract in the rat. Exptl. Eye Res. 9, 198 (1970).

    Article  CAS  Google Scholar 

  • Redemann, C. T.: The fate of 4-amino-3,5,6-trichloropicolinic acid in the dog. 150th Meeting Amer. Chem. Soc., Pest. Subdiv., Atlantic City, p. 16a (1965 a).

    Google Scholar 

  • Redemann, C. T.: The fate of 4-amino-3,5,6-trichloropicolinic acid in the rat. 150th Meeting Amer. Chem. Soc., Pest. Subdiv., Atlantic City, p. 17a (1965 b).

    Google Scholar 

  • Reiser, R. W.: Mass spectra of substituted uracils. Org. Mass Spec. 2, 467 (1969).

    Article  CAS  Google Scholar 

  • Rhodes, R. C, R. W. Reiser, J. A. Gardiner, and H. Sherman: Identification of the metabolites of terbacil in dog urine. J. Agr. Food Chem. 17, 974 (1969).

    Article  CAS  Google Scholar 

  • Rodgers, C. A.: Uptake and elimination of simazine by green sunfish (Lepomis cyanellus Raf.). Weed Sci. 18, 134 (1970).

    CAS  Google Scholar 

  • Rowles, S. G., G. S. Born, J. E. Christian, and W. V. Kessler: Metabolic fate of 2,3,5-triiodobenzoic acid in laying hens. J. Pharm. Sci. 59, 257 (1970).

    Article  PubMed  CAS  Google Scholar 

  • St. John, L. E., Jr., and D. J. Lisk: Fate of the herbicides bromoxynil and casoron in cows. J. Dairy Sci. 50, 582 (1967).

    Article  Google Scholar 

  • St. John, L. E., Jr., and D. J. Lisk: Excretory pathway of amiben in a lactating cow. J. Agr. Food Chem. 18, 482 (1970 a).

    Article  Google Scholar 

  • St. John, L. E., Jr., and D. J. Lisk: Metabolic studies with zytron herbicide in a lactating cow. J. Agr. Food Chem. 18,125 (1970 b).

    Article  Google Scholar 

  • St. John, L. E., Jr., J. W. Ammering, D. G. Wagner, R. G. Warner, and D. J. Lisk: Fate of 4,6-dinitro-2-isobutylphenol, 2-chloro-4,6-bis (ethylamino) -s-triazine, and penta-chloronitrobenzene in the dairy cow. J. Dairy Sci. 48, 502 (1965).

    Article  Google Scholar 

  • St. John, L. E., Jr., D. G. Wagner, and D. J. Lisk: Fate of atrazine, kuron, silvex, and 2,4,5-T in the dairy cow. J. Dairy Sci. 47, 1267 (1964).

    Article  Google Scholar 

  • Smith, J. N., R. H. Smithies, and R. T. Williams: Studies in detoxication. 48. Urinary metabolites of 4:6-dinitro-o-cresol in the rabbit. Biochem. J. 54, 225 (1953).

    PubMed  CAS  Google Scholar 

  • Sonawane, B. R., and C. O. Knowles: Comparative metabolism of two carbanilate herbicides (EP-475 and phenmedipham) in rats. Pest. Biochem. Physiol. 1, 472 (1971).

    Article  CAS  Google Scholar 

  • Stevens, M. A., and J. K. Walley: Tissue and milk residues arising from the ingestion of single doses of diquat and paraquat by cattle. J. Sci. Food Agr. 17, 472 (1966).

    Article  CAS  Google Scholar 

  • Thompson, W. T.: Agriculture chemicals, Book II-Herbicides. Davis, CA: Simmons Publishing Company (1964).

    Google Scholar 

  • Truhaut, R., and E. De Lavaur: Etude du métabolisme du dinitro-4.6 orthocresol chez le lapin. Acad. Sci. Paris, Ser. D 264, 1937 (1967).

    CAS  Google Scholar 

  • Tye, R., and D. Engel: Distribution and excretion of dicamba by rats as determined by radiotracer technique. J. Agr. Food Chem. 15, 837 (1967).

    Article  CAS  Google Scholar 

  • van Genderen, H., and G. J. van Esch: Toxicology of the herbicide dichlobenil (2,6-dichlorobenzonitrile) and its main metabolites. Food Cosmet. Toxicol. 6, 261 (1968).

    Article  PubMed  Google Scholar 

  • Williams, C. H., and K. H. Jacobson: An acylamidase in mammalian liver hydro-lyzing the herbicide 3,4-dichloropropionanilide. Toxicol. Applied Pharmacol. 9, 495 (1966).

    Article  CAS  Google Scholar 

  • Williams, P. P., and V. J. Feil: Identification of trifluralin metabolites from rumen microbial cultures. Effect of trifluralin on bacteria and protozoa. J. Agr. Food Chem. 19,1198 (1971).

    Article  CAS  Google Scholar 

  • Williams, P. P., and V. J. Feil, K. L. Davison, and E. J. Thacker: In vitro and in vivo rumen microbiological studies with 2-chloro-4,6-bis(isopropylamino)-5-triazine (propazine). J. Animal Sci. 27,1472 (1968).

    CAS  Google Scholar 

  • Williams, R. T.: Detoxication mechanisms, 2nd ed., London: Chapman & Hall (1959).

    Google Scholar 

  • Wilson, C. O., O. Gisvold, and R. E. Doerge: Textbook of organic, medicinal and pharmaceutical chemistry, 6th ed. Philadelphia: Lippincott (1971).

    Google Scholar 

  • Wit, J. G., and H. van Genderen: Metabolism of the herbicide 2,6-dichlorobenzo-nitrile in rabbits and rats. Biochem. J. 101, 698 (1966 a).

    PubMed  CAS  Google Scholar 

  • Wit, J. G., and H. van Genderen: The monophenolic metabohtes of the herbicide 2,6-dichlorobenzonitrile in animals as uncouplers of oxidative phosphorylation. Biochem. J. 101, 707 (1966 b).

    PubMed  CAS  Google Scholar 

  • Wright, F. C., J. C. Renter, J. S. Palmer, and J. C. Schlinke: Metabolic and residue studies with 2-(2,4,5-trichlorophenoxy)-ethyl 2,2-dichloropropionate (Erbon) herbicide in sheep. J. Agr. Food Chem. 18, 845 (1970).

    Article  CAS  Google Scholar 

  • Yre, R. Y., and C. Swithenbank: Identification of metabohtes of N-(l,l-dimethyl-propynyl)-3,5-dichlorobenzamide in rat and cow urine and rat feces. J. Agr. Food Chem. 19, 320 (1971).

    Article  Google Scholar 

  • Zeelinski, W. L., Jr., and L. Fishbein: Gas chromatographic measurement of disappearance rates of 2,4-D and 2,4,5-T acids and 2,4-D esters in mice. J. Agr. Food Chem. 15, 841 (1967).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Metabolism and Radiation Research Laboratory, United States Department of Agriculture, Agricultural Research Service, Fargo, ND, 58102, USA

    G. D. Paulson

Authors
  1. G. D. Paulson
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Entomology, University of California, Riverside, California, 92502, USA

    Francis A. Gunther  & Jane Davies Gunther  & 

Rights and permissions

Reprints and permissions

Copyright information

© 1975 Springer-Verlag New York Inc.

About this paper

Cite this paper

Paulson, G.D. (1975). Metabolic fates of herbicides in animals. In: Gunther, F.A., Gunther, J.D. (eds) Residue Reviews. Residue Reviews, vol 58. Springer, New York, NY. https://doi.org/10.1007/978-1-4613-9394-8_1

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-9394-8_1

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4613-9396-2

  • Online ISBN: 978-1-4613-9394-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation