The photochemistry of halogenated herbicides

  • J. R. Plimmer
Conference paper
Part of the Residue Reviews/Rückstandsberichte book series (RECT, volume 33)


The scope of this review has been limited primarily to the photochemical loss of halogen from herbicides, although some discussion of competitive and subsequent photolysis of pathways of individual herbicides has been included. The common names [1] approved by the Weed Science Society of America (Weed Society of America 1967) have been used.


Benzoic Acid Phenylacetic Acid Photosensitize Oxidation Chloranilic Acid Bond Fission 
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  1. Aly, O. M., and S. D. Faust: Studies on the fate of 2,4-D and ester derivatives in natural surface waters. J. Agr. Food Chem. 12, 541 (1964).CrossRefGoogle Scholar
  2. Barltrop, J. A., N. J. Bunce, and A. Thomson: Organic photochemistry. Part IV. Photonucleophilic substitution: Reactions of monosubstituted benzenes. J. Chem. Soc. C, p. 1142 (1967).Google Scholar
  3. Bell, G. R.: Photochemical degradation of 2,4-dichlorophenoxyacetic acid and structurally related compounds in the presence of riboflavin. Botan. Gaz. 118, 133 (1956).CrossRefGoogle Scholar
  4. Blair, J. McDonald and D. Bryce-Smith: Liquid phase photolysis. Part II. Iodobenzene. J. Chem. Soc., p. 1788 (1960).Google Scholar
  5. Blair, J. Mc Donald, and B. W. Pengilly: Liquid phase photolysis. Part I. Variation of isomer ratios with radical source in the phenylation of isopropylbenzene. Photolytic generation of phenyl radicals. J. Chem Soc., p. 3174 (1959).Google Scholar
  6. Calvert, J., and J. N. Pitts, Jr.: Photochemistry. New York: Wiley (1966).Google Scholar
  7. Comes, R. D., and F. L. Timmons: Effect of sunlight on the phytotoxicity of some phenylurea and triazine herbicides on a soil surface. Weeds 13, 81 (1965).CrossRefGoogle Scholar
  8. Crosby, D. G.: Photochemistry of herbicides. 154th Amer. Chem. Soc. Nat. Meeting, New York (1966).Google Scholar
  9. Crosby, D. G., and M-Y Li: Herbicide photodecomposition. In: Degradation of herbicides. P. C. Kearney and D. D. Kaufman (eds.). New York: Dekker (1969).Google Scholar
  10. Crosby, D. G., and H. O. Tutass: Photodecomposition of 2,4-dichlorophenoxyacetic acid. J. Agr. Food Chem. 14, 596 (1966).CrossRefGoogle Scholar
  11. Daniels, D. G. H., and B. C. Saunders: Studies in peroxidase action. Part VIII. The oxidation of p-chloroaniline. A reaction involving dechlorination. J. Chem. Soc., p. 822 (1953).Google Scholar
  12. Elad, D., D. V. Rao, and V. I. Stenberg: The photoanilide rearrangement. J. Org. Chem. 30, 3252 (1965).CrossRefGoogle Scholar
  13. Ercegovich, C. D.: What happens to the triazines in soil? Ardsley, New York, p. 22 (1965).Google Scholar
  14. Euler, H.: Über die Lichtspaltung von Halogen-Essigsäuren in Benzol und Äther. Chem. Ber. 49, 1366 (1916).CrossRefGoogle Scholar
  15. Foote, C. S.: Photosensitized oxygenations and the role of singlet oxygen. Accounts Chem. Research 1, 104 (1968 a).CrossRefGoogle Scholar
  16. Foote, C. S.: Mechanisms of photosensitized oxidation. Science 162, 963 (1968).PubMedCrossRefGoogle Scholar
  17. Geissbühler, H., Haselbach, H. Aebi, and L. Ebner: The fate of N’-(4-chlor- ophenoxy)-phenyl-NN-dimethylurea (C-1983) in soils and plants. III. Breakdown in soils and plants. Weed Research 3, 277 (1963).CrossRefGoogle Scholar
  18. Hall, R. C., C. S. Giam, and M. G. Merkle: The degradation of picloram by light. Weed Sci. Soc. Amer. Nat. Meeting, New Orleans, La., Abstr. p. 20 (1968).Google Scholar
  19. Hamadmad, N.: Photolysis of pentachloronitrobenzene, 2,3,5,6-tetrachloronitroben- zene, and pentachlorophenol. Thesis, Univ. of Calif., Davis, Calif. (1967) [Quoted in Crosby (1969), ref. 67].Google Scholar
  20. Henderson, W. A., Jr., and G. Zweig: Photolytic rearrangement and halogen dependent photocyclization of halophenyl naphthalenes. J. Amer. Chem. Soc. 89, 6778 (1967).CrossRefGoogle Scholar
  21. Isensee, A. R., J. R. Plimmer, and B. C. Turner: The effect of light on the herbicidal activity of some amiben derivatives. Weed Sci. Soc. Amer. Nat. Meeting, Las Vegas, Nev., Abstr. No. 224 (1969)Google Scholar
  22. Jordan, L. S., B. E. Day, and W. A. Clerx: Photodecomposition of triazines. Weeds 12, 5 (1964 a).CrossRefGoogle Scholar
  23. Jordan, L. S., C. W. Coggins, B. E. Day, and W. A. Clerx: Photodecomposition of substituted phenylureas. Weeds 12, 1 (1964 b).CrossRefGoogle Scholar
  24. Jordan, L. S., J. D. Mann, and B. E. Day: Effects of ultraviolet light on herbicides. Weeds 13, 43 (1965).CrossRefGoogle Scholar
  25. Joschek, H. I., and L. I. Grossweiner: Optical generation of hydrated electrons from aromatic compounds. II. J. Amer. Chem. Soc. 88, 3261 (1966).CrossRefGoogle Scholar
  26. Joschek, H. I., and L. I. Grossweiner: Photocleavage of phenoxyphenols and bromophenols. J. Amer. Chem. Soc. 88, 3269 (1966).CrossRefGoogle Scholar
  27. Joussot-Dubien, J., and J. Houdard: Reversible photolysis of pyridine in aqueous solution. Tetrahedron Letters, p. 4389 (1967).Google Scholar
  28. Kearney, P. C., E. A. Woolson, J. R. Plimmer, and A. R. Isensee: Decontamination of pesticide residues in soils. Residue Reviews 29, 137 (1969).PubMedGoogle Scholar
  29. Kharasch, N., and R. K. Sharma: Oxygen effects in the photolysis of 4-iodobi-phenyl in benzene. Chem. Commun., p. 106 (1966).Google Scholar
  30. Kharasch, N., R. K. Sharma, and H. B. Lewis: The photolysis of 4-bromobiphenyl in benzene. Chem. Commun., p. 418 (1966).Google Scholar
  31. Koller, L. R.: Ultraviolet radiation (2ed.). New York: Wiley (1966).Google Scholar
  32. Kuwahara, M., N. Kato, and K. Munakata: The photochemical reaction of pentachlorophenol. Part I. The structure of the yellow compound. Agr. Biol. Chem. 30, 232 (1966 a).CrossRefGoogle Scholar
  33. Kuwahara, M., N. Kato, and K. Munakata: The photochemical reaction of pentachlorophenol. Part II. The chemical structures of minor products. Agr. Biol. Chem. 30, 239 (1966 b).CrossRefGoogle Scholar
  34. Mitchell, L. C.: The effect of ultraviolet light (2537 A) on 141 pesticide chemicals by paper chromatography. J. Assoc. Official Agr. Chemists 44, 643 (1961).Google Scholar
  35. Neckers, D. C.: Mechanistic organic photochemistry. New York: Rheinhold (1967).Google Scholar
  36. Nijhoff, D. E., and E. Havinga: Photoreactions of aromatic compounds. VIII. A photochemical substitution of halogen in 2-bromo-(chloro)-4-nitroanisole. Tetrahedron Letters 47, 4199 (1965).CrossRefGoogle Scholar
  37. Penfound, W. T., and V. Minyard: Relation of light intensity to effect of 2,4- dichlorophenoxyacetic acid on water hyacinth and kidney bean plants. Botan. Gaz. 109, 231 (1947).CrossRefGoogle Scholar
  38. Plimmer, J. R.: Photolysis of amiben. Weed Sci. Soc. Amer. Abstr. p. 76, Washington, D.C. (1967).Google Scholar
  39. Plimmer, J. R., and B. E. Hummer: Photodecomposition of 2,3,6-trichlorobenzoic acid. Weed Sci. Soc. Amer. Abst. p. 20, New Orleans, La. (1968 a).Google Scholar
  40. Plimmer, J. R., and B. E. Hummer: Photochemistry of herbicides: A study of some chlorinated compounds. 155th Amer. Chem. Soc. Nat. Meeting, San Francisco (1968 b).Google Scholar
  41. Plimmer, J. R., and B. E. Hummer: Unpublished data (1968 c).Google Scholar
  42. Plimmer, J. R., and B. E. Hummer: Photolysis of amiben (3-amino-2,5-dichlorobenzoic acid) and its methyl ester. J. Agr. Food Chem. 17, 83 (1969).CrossRefGoogle Scholar
  43. Plimmer, J. R., B. E. Hummer, and U. I. Klingebiel: Unpublished data (1968).Google Scholar
  44. Rosen, J. D., and R. F. Strusz: Photolysis of 3-(p-bromophenyl)-l-methoxy-l- methylurea. J. Agr. Food Chem. 16, 568 (1968).CrossRefGoogle Scholar
  45. Rosen, J. D., R. F. Strusz, and J. D. Still: Further studies concerning the photolysis of urea herbicides. J. Agr. Food Chem. (in press) (1969).Google Scholar
  46. Santhanam, M., and V. Ramakrshnan: Photosensitized oxidation of aniline. Indian J. Chem., pp. 88–90 (1968).Google Scholar
  47. Sheets, T. J.: Photochemical alteration and inactivation of amiben. Weeds 11, 186 (1963).CrossRefGoogle Scholar
  48. Slade, P.: Photochemical degradation of paraquat. Nature 207, 515 (1965).CrossRefGoogle Scholar
  49. Smith, G. N.: Ultraviolet light decomposition studies with Dursban* and 3,5,6- trichloro-2-pyridinol. J. Econ. Entomol. 61, 794 (1968).Google Scholar
  50. Szychlinski, J.: Wstepne badania organicznych produktow fotolizy bromobenzenu w roztworze metanolowym. Zeszyty Nauk. Mat., Fiz., Chem., Wyzsza Skola Pedagog. Gdansk 3, 127 (1963).Google Scholar
  51. Szychlinski, J., and L. Litwin: Badania nad fotochemia chlorowcopochodnych aromatycznych VI. Roczniki Chem. 37, 671 (1963).Google Scholar
  52. Tang, C-S., and D. G. Crosby: Photodecomposition of 3-(p-chlorophenyl)-l,l- dimethylurea (Monuron). 156th Amer. Chem. Soc. Nat. Meeting, Atlantic City, N.J. (1968).Google Scholar
  53. Turro, N. J.: Photochemical reactivity. J. Chem. Ed. 44, 536 (1967).CrossRefGoogle Scholar
  54. Turro, N. J.: Molecular photochemistry. New York: Benjamin (1965).Google Scholar
  55. Ugochukwu, E. N., and R. L. Wain: Photolysis of 3,5-diiodo-4-hydroxy-benzoni- trile (Ioxynil) as a factor in its herbicidal action. Chem. Ind. (London), p. 35 (1965).Google Scholar
  56. Walczak, M., and J. Szychlinski: Kinetya fotolizy isomerow kwasu chloroben- zoesowego. Zeszyty Nauk. Mat., Fiz., Chem., Wyzsza Skola Pedagog. Gdansk. 3, 117 (1963).Google Scholar
  57. Weed Society of America. Herbicide handbook. Geneva, N.Y.: Humphrey Press (1967).Google Scholar
  58. Weldon, L. W., and F. L. Timmons: Photochemical degradation of diuron and monuron. Weeds 9, 111 (1961).CrossRefGoogle Scholar
  59. Wolf, W., and N. Kharasch: Photolysis of iodoaromatic compounds in benzene. J. Org. Chem. 30, 2493 (1965).CrossRefGoogle Scholar
  60. Wight, W. L., and G. F. Warren: Photochemical decomposition of trifluralin. Weeds 13, 329 (1965).CrossRefGoogle Scholar
  61. Ziffer, H., and N. Sharpless: Extension of the Hammett equation to photochemical quantum yields. J. Org. Chem. 27, 1944 (1962).CrossRefGoogle Scholar

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© Springer-Verlag New York Inc. 1970

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