Toxicity of natural chromene derivatives to a grasshopper

Isman, Murray B.; Yan, Jwo-Yee; Proksch, Peter

doi:10.1007/bf00367198

Cited by 20 publications

(10 citation statements)

References 7 publications

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“…Although relative sensitivities vary, lethal toxicity of both precocenes and acetyl-chromenes (those from Encelia species) appears to be widespread. Susceptible insects represent five orders, and many orders of insects are either untested or the results not reported (for examples, see Klocke et al, 1985;Wilkins & Sim, 1983;Isman & Proksch, 1985;Isman et al, 1986). As in our earlier report (Isman & Proksch, 1985), the benzofurans from E. farinosa and related species and genera essentially lack insecticidal activity, relative to the chromenes.…”

Section: Discussionmentioning

confidence: 73%

Insecticidal chromenes from the Asteraceae: structure-activity relations

Isman¹,

Proksch²,

Yan³

1987

Entomologia Experimentalis Et Applicata

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Chromenes (benzopyrans), common to many genera of the Asteraceae, are lethal to the neonate variegated cutworm, Peridrorna saucia Hiibner, when presented on the inner walls of glass vials at concentrations of 1.0 #mol/vial or less. Closely related benzofurans, including some from the same plants, are relatively inactive at these concentrations. The most potent of seven naturally-occurring and four derived chromenes is the well known allatocidin, precocene II, with an LDs0 of 0.134 t~mol/vial or 0.67 #g/cm 2. A more widely distributed chromene, desmethoxyencecalin, is also relatively toxic with an LDs0 of 0.98 #g/cm 2.Structure-activity comparisons of the chromenes tested in this study suggest that the presence of a free hydroxyl group at either C-7 or C-11 significantly diminishes activity. Saturation of the 3,4 double bond, which destroys the allatocidal activity of the precocenes, diminishes, but does not alleviate, contact toxicity of chromenes to cutworm larvae. Brief exposure (24 h) of 2-day-old larvae to chromene residues significantly inhibits subsequent larval growth. The degree of chronic growth inhibition (sublethal toxicity) from five different chromenes is highly correlated to their lethal potencies to neonate larvae.

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Section: Discussionmentioning

confidence: 73%

Insecticidal chromenes from the Asteraceae: structure-activity relations

Isman¹,

Proksch²,

Yan³

1987

Entomologia Experimentalis Et Applicata

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“…), is insecticidal to a wide range of insect species [3-61, including some considered insensitive to the antihormonal effects of the precocenes. In our previous investigations of structureactivity relations for the insecticidal actions of acetylchromenes [6,7], we found that compounds possessing free hydroxyl groups were significantly less toxic to both cutworms and grasshoppers. In particular, the 7-demethyl derivative of encecalin (2) is significantly less toxic than encecalin in insects from four different orders so far tested [4-61. In the present report, we investigate differences in pharmacokinetics and metabolism between encecalin and DME* in the migratory grasshopper, Melanoplus sanguinipes.…”

Section: Introductionmentioning

confidence: 87%

“…LDS0 values for the acetylchromenes to neonate hoppers were obtained via the residue-contact bioassay [6].…”

Section: Methodsmentioning

confidence: 99%

Metabolism and excretion of acetylchromenes by the migratory grasshopper

Isman

Proksch

Witte

1987

Arch Insect Biochem Physiol

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The extent of metabolism and excretion of three acetylchromenes (two toxic, one relatively nontoxic) were examined in adult migratory grasshoppers (Melanoplus sanguinipes) following topical administration. Both the total amount excreted (parent plus metabolites) and the proportion of parent compound in the excreta were inversely correlated with contact toxicity. Both toxic and nontoxic acetylchromenes are rapidly absorbed from the cuticle, with maximum excretion of parent and metabolite chromenes from 4 to 8 h posttreatment in each case. Much of the applied compounds (6040%) apparently remains within the insect, and cannot be recovered by extraction of the insect. Metabolites formed result from simple oxidative and reductive transformations. For all of the compounds tested (including the allatocidin precocene II), the major mode of metabolism results from aliphatic hydroxylation of one of the geminal methyl groups on the chromene. N o conjugated metabolites were found in the excreta.

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“…Precocenes are originally plant-derived chromenes (2H-1-benzopyran) with insecticidal activities (Proksch et al, 1983;Isman et al, 1986). On the basis of their functions, precocenes can be described as JH inhibitors or anti-JH agents (Staal, 1986).…”

Section: Introductionmentioning

confidence: 99%

Disruptive Impact of Precocene I (juvenile hormone-antagonist) on the Adult Performance and Reproductive Potential of the Egyptian Cotton Leafworm Spodoptera littoralis Boisduval (Lepidoptera: Noctuidae)

Ghoneim

Bosly

2017

Egyptian Academic Journal of Biological Sciences. A, Entomology

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The cotton leafworm, Spodoptera littoralis is destructive pest of cotton and various crops all over the year. The present study was carried out aiming to assess the effects of Precocene I (PI) on the most important parameters of adult performance and reproductive potential of this pest. Five sublethal doses: 150, 120, 90, 30 and 15 µg/larva had been topically applied (once) onto 1-day old larvae of 5 th (penultimate) instar and 6 th (last) instar. The adult emergence was slightly, or drastically, blocked, depending on the dose level and larval instar under treatment. PI exhibited a slightly extended toxic effect on the adult females only with the higher two doses. Some adult deformities were produced after treatment of 6 th instar larvae with PI. With regard to the adult longevity, the major effect of PI was the promotion of adult females to live longer lifetime. Both preoviposition and oviposition periods had been slightly, or considerably, shortened. After topical application of PI onto 5 th instar larvae, the oviposition rate was drastically regressed only at the lower two doses. After treatment of 6 th instar larvae with PI, the oviposition rate was drastically regressed in a dose-dependent course. Both fecundity and fertility were dramatically reduced. Complete sterility was recorded after treatment of 5 th instar larvae with PI but complete sterility had been recorded after treatment of 6 th instar larvae only with 150 and 30 µg/larva. The incubation period was remarkably prolonged.

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Toxicity of natural chromene derivatives to a grasshopper

Cited by 20 publications

References 7 publications

Insecticidal chromenes from the Asteraceae: structure-activity relations

Insecticidal chromenes from the Asteraceae: structure-activity relations

Metabolism and excretion of acetylchromenes by the migratory grasshopper

Disruptive Impact of Precocene I (juvenile hormone-antagonist) on the Adult Performance and Reproductive Potential of the Egyptian Cotton Leafworm Spodoptera littoralis Boisduval (Lepidoptera: Noctuidae)

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