Herbicidal Activity and Site of Action of the Natural Product Sorgoleone

Inhibition of photosynthetic electron transport in isolated spinach (Spinacea oleraceaL.) thylakoids and competitive binding to spinach, redroot pigweed (Amaranthus retroflexusL.), and potato (Solanum tuberosumL.) thylakoids were investigated for sorgoleone (2-hydroxy-5-methoxy-3-[(8′Z, 11′Z)-8′,11′...

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Bibliographic Details
Published in:Pesticide biochemistry and physiology 1996-01, Vol.54 (1), p.73-83
Main Authors: Nimbal, Chandrashekhar I., Yerkes, Carla N., Weston, Leslie A., Weller, Stephen C.
Format: Article
Language:English
Subjects:
AMARANTHUS
ATRAZINA
ATRAZINE
DIURON
EXSUDAT
EXUDADOS
FOTOSISTEMAS
HERBICIDAS
HERBICIDE
INHIBIDORES DE ENZIMAS
INHIBITEUR D'ENZYME
METRIBUZINA
METRIBUZINE
PHOTOSYSTEME
PLASTE
PLASTIDIOS
QUINONAS
QUINONE
RACINE
RAICES
SOLANUM TUBEROSUM
SORGHUM BICOLOR
SPINACIA OLERACEA
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Summary:Inhibition of photosynthetic electron transport in isolated spinach (Spinacea oleraceaL.) thylakoids and competitive binding to spinach, redroot pigweed (Amaranthus retroflexusL.), and potato (Solanum tuberosumL.) thylakoids were investigated for sorgoleone (2-hydroxy-5-methoxy-3-[(8′Z, 11′Z)-8′,11′,14′-pentadecatriene]-p-hydroquinone) in comparison with other photosystem II inhibitors. Sorgoleone inhibited photosynthetic electron transport as effectively as DCMU (diuron) [N′-(3,4-dichlorophenyl)-N,N-dimethylurea]. Rapid inhibition was observed by both compounds at concentrations of less than 0.2 μM.Sorgoleone competed with atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine] for binding to spinach, triazine-susceptible redroot pigweed or potato thylakoids as effectively as metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazine-5(4H)-one] or diuron. No competition was observed for bentazon [3-(methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide]. Double reciprocal plots in the presence or absence of 0.5 μMsorgoleone showed that sorgoleone is a competitive inhibitor of atrazine. Competitive binding was not observed in atrazine-resistant redroot pigweed or potato thylakoids. We conclude that sorgoleone is a potent inhibitor of photosynthetic electron transport and binds to the same QBniche of the D1 protein as diuron, atrazine, or metribuzin.
ISSN:0048-3575
1095-9939
DOI:10.1006/pest.1996.0011