Herbicidal action of 2-hydroxy-3-alkyl-1,4-naphthoquinones

A - Papers appearing in refereed journals

Jewess, P. J., Higgins, J., Berry, K. J., Moss, S. R., Boogaard, A. B. and Khambay, B. P. S. 2002. Herbicidal action of 2-hydroxy-3-alkyl-1,4-naphthoquinones. Pest Management Science. 58 (3), pp. 234-242. https://doi.org/10.1002/ps.428

AuthorsJewess, P. J., Higgins, J., Berry, K. J., Moss, S. R., Boogaard, A. B. and Khambay, B. P. S.

The main mode of herbicidal activity of 2-hydroxy-3-alkyl-1,4-naphthoquinones is shown to be inhibition of photosystem II (PSII). The herbicidal and in vitro activities have been measured and correlated with their (Log)octanol/water partition coefficients (Log K-o/w). The length of the 3-n-alkyl substituent for optimal activity differed between herbicidal and in vitro activity. The maximum in vitro activity was given by the nonyl to dodecyl homologues (Log K-o/w between 6.54 and 8.12), whereas herbicidal activity peaked with the n-hexyl compound (Log K-o/w = 4.95). The effect of chain branching was also investigated using isomeric pentyl analogues substituted at position 3. All exhibited similar levels of in vitro activities but herbicidal activities differed, albeit moderately, with the exception of one analogue that was much less phytotoxic. Other modes of action were also investigated using two representative compounds. They did not show any activity on photosystem I or mitochondrial complex I, or generate toxic oxygen radicals by redox cycling reactions. Only moderate activity was found against mitochondrial complex III from plants, in contrast to much higher corresponding activity using an insect enzyme. (C) 2002 Society of Chemical Industry.

KeywordsAgronomy; Entomology
Year of Publication2002
JournalPest Management Science
Journal citation58 (3), pp. 234-242
Digital Object Identifier (DOI)https://doi.org/10.1002/ps.428
PubMed ID11975168
Open accessPublished as non-open access
Funder project or code437

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