New Pyrethrin-Like Esters with High Insecticidal Activity

Elliott, M.; Janes, Norman F.; Jeffs, K. A.; Needham, P. H.; Sawicki, R. M.

doi:10.1038/207938a0

Cited by 38 publications

(14 citation statements)

References 5 publications

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“…Several synthetic pyrethroids are marketed either as single most active isomer or as a mixture of stereoisomers, in order to enhance activity, minimising toxicity [10 -12]. The object of this work was to develop suitable analytical methods for the analytical profile and quality control of dallethrin (DA) as raw material, which represents one of the most widely used pyrethroids [13]. DA is a mixture of esters derived from (1R, 3R) trans and (1R, 3S) cis chrysanthemic acid (CA) in the 80/20 ratio and (R) and (S) allethrolone (AL) (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

GC‐FID/MS method for the impurity profiling of synthetic d‐allethrin

Bragieri¹,

Liverani²,

Zanotti³

et al. 2004

J of Separation Science

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A GC/FID/MS method was developed for the identification and quantification of d-allethrin (DA) and its major impurities in commercial samples. Optimisation of the experimental conditions was carried out considering such important requirements as resolution, reproducibility, detection limits of 0.1% (m/m) for the impurities, and short analysis time. Under the optimised final conditions the method was validated for specificity, precision (CV% = 0.133 at 2.10 mg/mL and CV% = 0.035 at 3.00 mg/mL), linearity (0-3.00 microg injected), limits of detection (0.09 ng injected) and quantitation (0.28 ng injected), and robustness. The DA related impurities were identified by using a GC/MS method with ion trap mass detection and also by comparison with synthesised standards. The most abundant impurities were crysolactone, allethrolone, chrysanthemic acid, and chloro-derivatives of DA.

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Section: Introductionmentioning

confidence: 99%

GC‐FID/MS method for the impurity profiling of synthetic d‐allethrin

Bragieri¹,

Liverani²,

Zanotti³

et al. 2004

J of Separation Science

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“…The insecticidal activity of pyrethrin I depends on the overall structure of the ester, in particular on methyl groups at C-2 on the cyclopropane ring (23) maintained in a definite stereochemical disposition with respect to an unsaturated side chain at C-3 and the ester link at C-1 (24)(25)(26). Without steric constraint, the ester probably adopts an S-trans conformation (2,25,26) and, supported by the near-planar cyclopentenolone ring, the cis-pentadienyl side chain can adopt only certain orientations in space with respect to the features of the acid structure discussed above.…”

Section: Structure and Insecticidal Activitymentioning

confidence: 99%

Properties and applications of pyrethroids.

Elliott¹

1976

Environ Health Perspect

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Improved understanding of the factors determining the insecticidal activity, the mammalian toxicity, and the stability in air and light of natural and synthetic pyrethroids has led to a series of new compounds with a very favorable combination of properties. Their characteristicsinclude outstanding potency to insects, low toxicity to mammals associated with rapid metabolic breakdown and, in appropriate cases, adequate stability on plant surfaces even in bright sunlight. Initial tests indicate that even the more stable compounds are degraded rapidly in soil, so if the trials at present in progress reveal no toxicological or environmental hazards, within a few years synthetic pyrethroids should be available to control a wide range of domestic, veterinary, horticultural, agricultural, and forest pests at low rates of application.

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“…EXPERIMENTAL IR spectra were recorded on a Hitachi IR Spectrometer in film. NMR spectra were measured on a Hitachi Perkin-Elmer R-20 type (60 Mc) spectrometer in CCI 4 (unless otherwise stated) with TMS as internal standard. All the chrysanthemic acid used in our experiment were dl-cis, trans mixtures.…”

Section: S )mentioning

confidence: 99%

“…4 ) From our result for XV, it would be concluded that an appropriate steric relation for sufficient insect toxicity was held in the molecule of XV, as in the case of V, and then it would be able to use a triple bond as the structure connecting the unsaturated side chain with the acid moiety.…”

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confidence: 99%