Hostname: page-component-586b7cd67f-2brh9 Total loading time: 0 Render date: 2024-11-25T02:09:00.985Z Has data issue: false hasContentIssue false
  • English
  • Français

Modes of Action of Pyridazinone Herbicides

Published online by Cambridge University Press:  12 June 2017

J. L. Hilton ,
A. L. Scharen ,
J. B. St. John ,
D. E. Moreland  and
K. H. Norris
J. L. Hilton
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
A. L. Scharen
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
J. B. St. John
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
D. E. Moreland
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Crops Science Department, N. C. State University, Raleigh, North Carolina
K. H. Norris
Affiliation:
Instrumentation Research Laboratory, Market Quality Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
Get access Rights & Permissions [Opens in a new window]

Abstract

Four substituted pyridazinone compounds inhibited the Hill reaction and photosynthesis in barley (Hordeum vulgare L., var. Dayton C.I. 9517). These inhibitions appeared to account for the phytotoxicity of 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone (pyrazon). The pyridazinone chemicals were weaker inhibitors than 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine). Two substitutions onto the molecular structure of pyrazon result in a new experimental herbicide, 4-chloro-5-(dimethylamino)-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone (hereinafter referred to as 6706), which retains the action mechanism of pyrazon but also has two additional biological properties. It is resistant to metabolic detoxication in plants, and it possesses a second mode of action involving interference with chloroplast development. The second action is like that expressed by 3-amino-s-triazole (amitrole) and by 3,4-dichlorobenzyl methylcarbamate (dichlormate). However, the new chemical is 100 to 1000 times more effective. The trifluoromethyl substitution on the phenyl ring and the dimethyl substitution on the amine are both required to give either of the two additional physiological properties. Analogs with only one of the two substitutions behave like pyrazon rather than like 6706.

Type
Research Article
Information
Weed Science , Volume 17 , Issue 4 , October 1969 , pp. 541 - 547
Copyright
Copyright © 1969 Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

1. Arnon, D. I. 1949. Copper enzymes in isolated chloroplasts. Polyphenoloxidase in Beta vulgaris . Plant Physiol. 24:1–15.Google Scholar
2. Avron, M. 1960. Photophosphorylation by Swiss chard chloroplasts. Biochim. Biophys. Acta. 40:257–272.CrossRefGoogle ScholarPubMed
3. Bartels, P. G. and Pegelow, E. J. Jr. 1968. The action of sirmate (3,4-dichlorobenzyl methylcarbamate) on chloroplast ribosomes in Triticum vulgare L. seedlings. J. Cell Biol. 37: C1–C6.Google Scholar
4. Bartels, P. G., Matsuda, K., Siegel, A. and Weiser, T. E. 1967. Chloroplastic ribosome formation. Inhibition by 3-amino-1, 2,4-triazole. Plant Physiol. 42:736–741.Google Scholar
5. Bartels, P. G., and Wolf, F. T. 1967. Anthocyanin pigment formation in wheat seedlings following treatment with amitrole. Biochim. Biophys. Acta. 136:166–168.Google Scholar
6. Herrett, R. A. and Berthold, R. V. 1965. 3,4-dichlorobenzyl methylcarbamate and related compounds as herbicides. Science 149:191–193.Google Scholar
7. Hilton, J. L., Jansen, L. L. and Hull, H. M. 1963. Mechanisms of herbicide action. Ann. Rev. Plant Physiol. 14:353–384.Google Scholar
8. Hilton, J. L., Monaco, T. J., Moreland, D. E., and Gentner, W. A. 1964. Mode of action of uracil herbicides. Weeds 12: 129–131.Google Scholar
9. Moreland, D. E. 1967. Mechanisms of action of herbicides. Ann. Rev. Plant Physiol. 18:365–386.Google Scholar
10. Moreland, D. E., Gentner, W. A., Hilton, J. L., and Hill, K. L. 1959. Studies on the mechanism of herbicidal action of 2-chloro-4,6-bis-(ethylamino)-s-triazine. Plant Physiol. 34:432–435.Google Scholar
11. Norris, K. H. and Butler, W. L. 1961. Techniques for obtaining absorption spectra on intact biological samples. IRE Trans. Bio-med. Electron. BME-8:153–157.Google Scholar
12. Ries, S. K., Zabik, M. J., Stevenson, G. R., and Chen, T. M. 1968. N-glucosyl metabolite of pyrazon in red beets. Weed Sci. 16:40–41.Google Scholar
13. Scharen, A. L. and Taylor, J. M. 1968. CO2 assimilation and yield of little club wheat infected by Septoria nodorum . Phytopathology 58:447–451.Google Scholar
14. Stephenson, G. R. and Ries, S. K. 1967. The movement and metabolism of pyrazon in tolerant and susceptible species. Weed Res. 7:51–60.Google Scholar
15. Stephenson, G. R. and Ries, S. K. 1969. Metabolism of pyrazon in sugar beets and soil. Weed Sci. 17:327–331.Google Scholar
16. Van Oorschot, J. L. P. 1965. Selectivity and physiological inactivation of some herbicides inhibiting photosynthesis. Weed Res. 5:84–97.Google Scholar
17. Wolf, F. T. 1960. Influence of amino triazole on the chloroplast pigments of wheat seedlings. Nature 188:164–165.Google Scholar