Hostname: page-component-7b7567c8c-7pwfn Total loading time: 0 Render date: 2026-11-15T11:31:57.695Z Has data issue: false hasContentIssue false
  • English
  • Français

N-Alkylaryltriazine Herbicides: A Possible Link Between Triazines and Phenylureas

Published online by Cambridge University Press:  12 June 2017

Gary Gardner,
James R. Sanborn and
John R. Goss
Gary Gardner
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
James R. Sanborn
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
John R. Goss
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
Get accessRights & Permissions [Opens in a new window]

Abstract

A comparison of the structure of the α-methylbenzyl analogue (MBAT) of atrazine with the Photosystem II herbicides atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine] and diuron [N′-(3,4-dichlorophenyl)-N,N-dimethylurea] suggested that N-alkylbenzyltriazines may be a structural bridge between the triazines and the phenylureas. In the phenylureas, the addition of chlorines at the meta and/or para positions produces a marked increase in activity. Chloro-substituted derivatives of MBAT were synthesized to determine whether this structure-activity relationship also applies to the alkylaryltriazines. Addition of a chlorine to MBAT at the 4-position (CMBAT) caused a substantial increase in intrinsic activity, and a second chlorine at the 3-position (DCMBAT) caused a further increase. In direct comparisons, DCMBAT was more active in vitro than terbuthylazine [6-chloro-N-ethyl-N′-(1,1-dimethylethyl)-1,3,5-triazine-2,4-diamine], the most active chlorotriazine, and was also more active than diruon. The effects of DCMBAT were also measured on triazine-resistant pigweed (Amaranthus hybridus L. # AMACH) both in vivo and in vitro. The activity of this compound in triazine-resistant chloroplasts was intermediate between that of atrazine and diruon both in inhibition of photosynthetic electron transport and in competition for diuron binding sites, with half-maximal values falling in the micromolar range. Whole plant phytotoxicity of DCMBAT on triazine-resistant pigweed was also intermediate between that of diuron and atrazine. Since DCMBAT is a triazine with biological properties similar to that of a urea, we conclude that in a functional as well as structural sense, DCMBAT is a herbicide that is a hybrid between a triazine and a urea.

Keywords

Photosystem IIelectron transportbindinginhibitoratrazineresistancediuronstructure-activityPisum sativumAmaranthus hybridusAmaranthus retroflexusAMACHAMARE

Information

Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 35 , Issue 6 , November 1987, pp. 763 - 769
Copyright
Copyright © 1987 by the 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.)

Article purchase

Temporarily unavailable

References

Literature Cited

1. Borch, R. F., Bernstein, M. D., and Durst, H. D. The cyanohydridoborate anion as a selective reducing agent. 1971. J. Am. Chem. Soc. 93:2897–2912.Google Scholar
2. Ducruet, J. M. and De Prado, R. 1982. Comparison of inhibitory activity of amides derivatives in triazine-resistant and -susceptible chloroplasts from Chenopodium album and Brassica campestris . Pestic. Biochem. Physiol. 18:253–261.Google Scholar
3. Ebert, E. and Dumford, S. W. 1976. Effects of triazine herbicides on the physiology of plants. Residue Rev. 65:1–103.Google Scholar
4. Gardner, G., Allen, C. D., and Paterson, D. R. 1983. Modification of Photosystem II by phenylglyoxal: evidence for the involvement of arginine in atrazine binding to chloroplasts. FEBS Lett. 164:191–194.Google Scholar
5. Gardner, G., Pilgram, K. H., Brown, L. J., and Bozarth, G. A. 1985. In vitro activity of sorghum-selective fluorophenyl urea herbicides. Pestic. Biochem. Physiol. 24:285–297.Google Scholar
6. Gardner, G. and Sanborn, J. R. 1987. The role of chirality in the activity of Photosystem II herbicides. Z. Naturforsch. 42c:663–669.Google Scholar
7. Moreland, D. E. and Hill, K. L. 1962. Interference of herbicides with the Hill reaction of isolated chloroplasts. Weeds 10:229–236.Google Scholar
8. Oettmeier, W., Masson, K., Fedtke, C., Konze, J., and Schmidt, R. R. 1982. Effect of different Photosystem II inhibitors on chloroplasts isolated from species either susceptible or resistant toward s-triazine herbicides. Pestic. Biochem. Physiol. 18:357–367.CrossRefGoogle Scholar
9. Pfister, K. and Arntzen, C. J. 1979. The mode of action of Photosystem II–specific inhibitors in herbicide-resistant weed biotypes. Z. Naturforsch. 34c:996–1009.Google Scholar
10. Pfister, K., Radosevich, S. R., and Arntzen, C. J. 1979. Modification of herbicide binding to Photosystem II in two biotypes of Senecio vulgaris L. Plant Physiol. 64:995–999.CrossRefGoogle ScholarPubMed
11. Radosevich, S. R. and DeVilliers, O. T. 1976. Studies on the mechanism of s-triazine resistance in common groundsel. Weed Sci. 24:229–232.CrossRefGoogle Scholar
12. Radosevich, S. R., Steinback, K. E., and Arntzen, C. J. 1979. Effect of Photosystem II inhibitors on thylakoid membranes of two common groundsel (Senecio vulgaris) biotypes. Weed Sci. 27:216–218.CrossRefGoogle Scholar
13. Ryan, G. F. 1970. Resistance of common groundsel to simazine and atrazine. Weed Sci. 18:614–616.Google Scholar
14. Machado, V. Souza, Arntzen, C. J., Bandeen, J. D., and Stephenson, G. R. 1978. Comparative triazine effects upon System II photochemistry in chloroplasts of two common lambsquarters (Chenopodium album) biotypes. Weed Sci. 26:318–322.CrossRefGoogle Scholar
15. Tischer, W. and Strotmann, H. 1977. Relationship between inhibitor binding by chloroplasts and inhibition of photosynthetic electron transport. Biochim. Biophys. Acta 460:113–125.CrossRefGoogle ScholarPubMed
16. Trebst, A. and Draber, W. 1979. Structure activity correlations of recent herbicides in photosynthetic reactions. Pages 223–234 in Geissbuehler, H., ed. Advances in Pesticide Science, Part 2, Oxford: Pergamon Press, 1979.Google Scholar