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Amino- and urea-substituted thiazoles inhibit photosynthetic electron transfer

Dayan, F.E., Vincent, A.C., Romagni, J.G., Allen, S.N., Duke, S.O., Duke, M.V., Bowling, J.J., Zjawiony, J.K.
Journal of agricultural and food chemistry 2000 v.48 no.8 pp. 3689-3693
gas production (biological), thiazoles, urea, herbicidal properties, photosynthesis, Lemna minor, Spinacia oleracea, oxygen, structure-activity relationships, molecular conformation, chemical structure, atrazine, diuron, thylakoids, electron transfer
Amino- and urea-substituted thiazoles exhibited in vivo herbicidal activity on duckweed (Lemna paucicostata Hegelm. strain 6746) cultures and appeared to act via inhibition of photosynthetic electron transport system. A small number of the thiazole derivatives tested were active but only at relatively high concentrations. The most active structures were the amino-substituted thiazoles with isopropyl and n-butyl side chains and the urea-substituted thiazole with p-chlorophenyl side chain. Decreasing the length of the side chain had a negative effect on the PSII inhibitory activity. The urea-substituted series was as a group less active than the amino series, and the free acid series had no biological activity. The most active compounds competed for the same binding site as atrazine on PSII. Computer modeling highlighted the structural similarities between some of the thiazoles and the commercial herbicides diuron and atrazine.