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Insecticidal 2‐hydroxy‐3‐alkyl‐1,4‐naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity
Author(s) -
Jewess Philip J,
Chamberlain Keith,
Boogaard Adrian B,
Devonshire Alan L,
Khambay Bhupinder P S
Publication year - 2002
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.445
Subject(s) - tetranychus urticae , stereochemistry , in vivo , chemistry , ec50 , octanol , oxidoreductase , biology , in vitro , enzyme , biochemistry , partition coefficient , mite , botany , organic chemistry , microbiology and biotechnology
The insecticidal and in vitro activities of four homologous series of 2‐hydroxy and acetoxy‐3‐substituted‐1,4‐naphthoquinones have been measured and correlated with their (Log) octanol/water partition coefficients (Log K o/w ). In vitro activity against mitochondrial complex III was only exhibited by 2‐hydroxy‐3‐alkyl‐1,4‐naphthoquinones, indicating that the 2‐acetoxy compounds act as pro‐insecticides. Good correlation was observed between in vivo activity against the two‐spotted spider mite, Tetranychus urticae and inhibition of complex III isolated from blowfly flight muscle. Both hydroxy and acetoxy analogues of individual compounds exhibited similar levels of in vivo activity with optimum activity for analogues with Log K o/w values of 7–8. In contrast, the acetoxy derivatives showed superior in vivo activity against the tobacco whitefly, Bemisia tabaci . Complex III isolated from whitefly was optimally inhibited by hydroxy analogues with lower Log K o/w values (6.0–6.5) and was also more sensitive than the blowfly enzyme to all the compounds tested. © 2002 Society of Chemical Industry