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Endothall and cantharidin analogues relation of structure to herbicidal activity and mammalian toxicity



Endothall and cantharidin analogues relation of structure to herbicidal activity and mammalian toxicity



Journal of Agricultural & Food Chemistry 35(5): 823-829



Analogues of the herbicide endothal (exo,exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid) with various ring substituents and including several geometrical isomers were synthesized via Diels-Alder reactions. They were assayed as inhibitors of root elongation in barnyard grass and wild mustard and for acute toxicity to mice on intraperitoneal administration. Studies with 43 analogues demonstrate the importance for herbicidal activity of the spatial arrangement of the bridged oxygen and the exo,exo positions of the two carboxylic acid groups. The exo,exo positions facilitate intramolecular hydrogen bonding and formation of stable metal ion complexes. The herbicidal activity of endothal is reduced on adding ring substituents due to steric hindrance around the bridged oxygen. Mammalian toxicity generally follows the same pattern except that 2,3-dimethyl substitution to form cantharidin increases activity. Somewhat similar structure-activity relationships for herbicidal activity and toxicity to mice suggest the possibility of a related oxabicycloheptane target site in plants and mammals.

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Accession: 005359850

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