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Mode of action of novel 2-(benzylamino)-4-methyl-6-(trifluoro-methyl)-1,3,5-triazine herbicides: inhibition of photosynthetic electron transport and binding studies

Author:
Ohki, A., Kuboyama, N., Koizumi, K., Tanaka, A., Sato, Y., Kohno, H., Boger, P., Wakabayashi, K.
Source:
Journal of agricultural and food chemistry 1999 v.47 no.10 pp. 4398-4402
ISSN:
0021-8561
Subject:
Chenopodium album, Spinacia oleracea, triazine herbicides, atrazine, herbicidal properties, photosynthesis, structure-activity relationships, plant proteins, thylakoids, electron transfer, D1 protein
Abstract:
Novel 2-(benzylamino)-4-methyl-6- (trifluoromethyl)-1,3,5-triazines have the same 1,3,5-triazine skeleton as atrazine, although some of them, for example, 2-(3-chlorobenzylamino)-4-methyl-6- (trifluoromethyl)-1,3,5-triazine [pI(50)(spinach) = 7.21], show a >3 times stronger photosynthetic electron transport inhibitory activity than atrazine [pI(50)(spinach) = 6.72]. The new triazines have only one amino group at the triazine ring, and their molecular shapes are different from atrazine. The replacement of the bound [(14)C]atrazine by 1,3,5-triazines was tested to determine whether the novel 1,3,5-triazine analogues exhibit the same binding pattern at the D1-protein as atrazine. It was found that [(14)C]atrazine bound to the Di-protein was replaced by the triazine tested by a clearly competitive interaction. Obviously, the novel 1,3,5 -triazines are attached to the same binding niche as atrazine.
Agid:
1372080