Insecticidal 2‐hydroxy‐3‐alkyl‐1,4‐naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity

Jewess, P. J.; Chamberlain, Keith; Boogaard, Adrian B; Devonshire, A. L.; Khambay, B. P. S.

doi:10.1002/ps.445

Cited by 16 publications

(8 citation statements)

References 24 publications

(25 reference statements)

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“…For example, there was no correlation between toxicity of a set of naphthoquinones against Tetrahymena pyriformis and log P (32). Along the same line, there was a poor correlation between the herbicidal activity of 2-hydroxy-3-alkyl-naphthoquinones and their lipophilicity (33), whereas there was a good correlation between the insecticidal activity of the same compounds and their lipophilicity (34).…”

Section: Resultsmentioning

confidence: 91%

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Activity of Quinones on Colletotrichum Species

Meazza

Dayan

Wedge

2003

J. Agric. Food Chem.

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The antifungal activity of 1,4-naphthoquinones, 1,2-naphthoquinones, 1,4-benzoquinones, and anthraquinones from our natural products collection was tested by direct bioautography to identify natural products with potential use in agricultural fungal pathogen control. Quinones demonstrated good to moderate antifungal activity against Colletotrichum spp. Colletotrichum fragariae was the most sensitive species to quinone-based chemistry, Colletotrichum gloeosporioides had intermediate sensitivity, while Colletotrichum acutatum was the species least sensitive to these compounds.

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Section: Resultsmentioning

confidence: 91%

“…Naturally occurring quinones are known for their biological activities. They possess antitumor, antiinflammatory, antiparasitic, antimicrobial, insecticidal, herbicidal, and fungicidal activities (33)(34)(35)(36)(37)(38)(39)(40). Quinones are known to inhibit electron transport involved in mitochondrial respiration (41).…”

Section: Resultsmentioning

confidence: 99%

Activity of Quinones on Colletotrichum Species

Meazza

Dayan

Wedge

2003

J. Agric. Food Chem.

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“…Extensive structure‐activity relationship studies resulted in the discovery of a range of novel pesticidal, and in particular insecticidal/miticidal, compounds that have been protected by four world‐wide families of patent applications 1. 3–5 They have been shown6, 7 to be respiratory inhibitors that act by inhibiting mitochondrial Complex III. The fungicidal properties of related 1,4‐naphthoquinones were investigated8 in detail at IACR‐Long Ashton during the 1970s; compounds with high levels of preventative activity but poor eradicant activity were identified.…”

Section: Introductionmentioning

confidence: 99%

Mode of action and pesticidal activity of the natural product dunnione and of some analogues

Khambay

Batty

Jewess

et al. 2003

Pest Management Science

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This paper reports the investigation of the insecticidal and fungicidal activity of dunnione, a natural product obtained inadvertently as a by-product of a synthesis programme. Dunnione exhibits no insecticidal activity but has an unusually broad spectrum of antifungal activity. In vitro and in vivo (preventative) activities were comparable to those of several long-established fungicides (eg carbendazim). However, in whole-plant assays, its eradicant activity was unexpectedly low, probably due to poor dose-transfer from leaf surface to fungus. The level of residual activity appears to be influenced by the formulation. Finally, its potential as a lead structure was assessed, and several analogues synthesised which exhibited high activity in the in vitro assays. Mode-of-action studies revealed that dunnione exerts its action primarily through initiation of redox cycling. This contrasts to the activity of BTG 505, the biochemical/chemical precursor, which does not initiate redox cycling but instead exhibits both insecticidal and fungicidal activity by inhibiting mitochondrial Complex III.

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“…Log P values of a series of test chemicals often follow predictable trends in biological assays [28]. Compounds with lower log P values are classified as polar, while those with higher log P values are considered more lipophilic with better membrane permeability [29]. However, we did not observe any correlation between Log P values for compounds 1 – 28 [30] and 29 [31] and male response in Experiment 1 ( r = 0.03037, n = 29, p = 0.8757) (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Laboratory Evaluation of Natural and Synthetic Aromatic Compounds as Potential Attractants for Male Mediterranean fruit Fly, Ceratitis capitata

et al. 2019

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Ceratitis capitata, the Mediterranean fruit fly, is one of the most serious agricultural pests worldwide responsible for significant reduction in fruit and vegetable yields. Eradication is expensive and often not feasible. Current control methods include the application of conventional insecticides, leading to pesticide resistance and unwanted environmental effects. The aim of this study was to identify potential new attractants for incorporation into more environmentally sound management programs for C. capitata. In initial binary choice bioassays against control, a series of naturally occurring plant and fungal aromatic compounds and their related analogs were screened, identifying phenyllactic acid (7), estragole (24), o-eugenol (21), and 2-allylphenol (23) as promising attractants for male C. capitata. Subsequent binary choice tests evaluated five semisynthetic derivatives prepared from 2-allylphenol, but none of these were as attractive as 2-allylphenol. In binary choice bioassays with the four most attractive compounds, males were more attracted to o-eugenol (21) than to estragole (24), 2-allylphenol (23), or phenyllactic acid (7). In addition, electroantennography (EAG) was used to quantify antennal olfactory responses to the individual compounds (1–29), and the strongest EAG responses were elicited by 1-allyl-4-(trifluoromethyl)benzene (11), estragole (24), 4-allyltoluene (14), trans-anethole (9), o-eugenol (21), and 2-allylphenol (23). The compounds evaluated in the current investigation provide insight into chemical structure–function relationships and help direct future efforts in the development of improved attractants for the detection and control of invasive C. capitata.

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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

Cited by 16 publications

References 24 publications

Activity of Quinones on Colletotrichum Species

Activity of Quinones on Colletotrichum Species

Mode of action and pesticidal activity of the natural product dunnione and of some analogues

Laboratory Evaluation of Natural and Synthetic Aromatic Compounds as Potential Attractants for Male Mediterranean fruit Fly, Ceratitis capitata

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