Potent Pyrethroid Insecticides from Modified Cyclopropane Acids

Elliott, M.; Farnham, Andrew W.; Janes, Norman F.; Needham, P. H.; Pulman, David A.

doi:10.1038/244456a0

Cited by 85 publications

(52 citation statements)

References 9 publications

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“…As a result, when radiolabled allethrin was orally administered to rats, several ester metabolites were obtained in rat urine, as shown in the reaction scheme (6). Although chrysanthemumic acid and allethrolone were detected as minor metabolites, the major ones are those oxidized at methyl groups in the acid moiety or at allyl group in allethrolone alcohol.…”

Section: Metabolism In Mammalsmentioning

confidence: 98%

“…Long-lasting, extensive efforts in many laboratories in modifying chemical structure of natural pyrethrins to obtain derivatives with better chemical properties and biological performances, have proved to be gradually successful, and numerous new compounds have been elaborated (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). Some compounds are quite different from natural pyrethrins in their alcoholic moiety, and others even lack the cyclopropane ring in the acid moiety.…”

Section: Introductionmentioning

confidence: 99%

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Degradation, metabolism and toxicity of synthetic pyrethroids.

Miyamoto¹

1976

Environ Health Perspect

201

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Synthetic pyrethroidal compounds undergo biodegradation in mammals both oxidatively and hydrolytically, and depending on the type of compound, either of the pathways may predominate. Thus, (+) -or (±) -trans isomers of the chrysanthemumate ester of primary alcohols such as fenothrin, furamethrin, proparthrin, resmethrin, and tetramethrin (and possibly permethrin, too) are metabolized mainly through hydrolysis of the ester linkage, with subsequent oxidation and/or conjugation of the component alcohol and acid moieties. On the other hand, the corresponding (+ )-cis enantiometers and chrysanthemumate of secondary alcohols like allethrin are resistant to hydrolytic attack, and biodegraded via oxidation at various sites of the molecule. These rapid metabolic degradations, together with the presumable incomplete absorption from the gastrointestinal tract, would generally contribute to the low acute toxicity of synthetic pyrethroids.These compounds are neither skin irritants nor skin sensitizers, and inhalation toxicity as well as dermal toxicity are fairly low. Neither is teratogenic in rats, mice, and/or rabbits or mutagenic on various bacterial strains. Subacute and chronic feeding of higher amounts of the compounds to rats invariably causes some histopathological changes in liver; however, these are neither indicative nor suggestive of tumorigenicity.Based on existing toxicological information, the present recommended use patterns might afford sufficient safety margin on human population.However, in extending usage to agricultural pest control, much more extensive investigations should be forthcoming from both chemical and biological aspects, since there is scant information on the fate of these pyrethroids in the environment. Also several of the compounds may be very toxic to certain kinds of fish and arthropods.

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Section: Metabolism In Mammalsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Degradation, metabolism and toxicity of synthetic pyrethroids.

Miyamoto¹

1976

Environ Health Perspect

201

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“…Currently, the two most common vector control interventions are long-lasting insecticidal nets (LLINs) and indoor residual spraying (IRS) [15]. Pyrethroids are particularly suitable for veterinary and public health purposes because of their quick knockdown effects, high insecticidal potency and relatively low mammalian hazard at operational doses [16,17]. In recent years, pyrethroids have been used for residual spraying in malaria control programme.…”

Section: Introductionmentioning

confidence: 99%

The Field Practices of Lambdacyhalothrin and Deltamethrin Insecticides Against Adult Mosquitoes of Anopheles stephensi as the Main Vector of Malaria: Residual Effects

Khosravani

Rafatpanah

Amiri

et al. 2017

Zahedan J Res Med Sci

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Background: Various chemical control methods have adopted in anti-malaria interventions. Indoor residual spraying (IRS) has been proven as a candidate in elimination program. On the other hand, resistance to multiple insecticides was implicated as a concern issue in these polices. Pesticides should be evaluated to identify probable resistant and make decision to choose a technique against vectors. Methods:In this cross-sectional study, Bioassay test applied on lambdacyhalothrin WP 10% (0.05 mg a.i. /m 2 ) and deltamethrin WP 5% (0.05 mg a.i./m 2 ) on two surfaces (cement and plaster) against adult mosquitoes of Anopheles stephensi according to WHO criteria to measure the residual activity in Saravan county, southern Iran. Overall, 3960 mosquitoes was used in our research. The mortality rates of An.stephensi Liston (Diptera: Culicidae) measured between selected surfaces and insecticides in several times. Data analyzed by Mann-Whitney (nonparametric test) using SPSS v22 statistic software.Results: This paper illustrated that maximal course of residual efficacy was about 3 months. No statistically significant different was exhibited between type of surface within mortality rates of An. Stephensi (P = 0.724) but lambdacyhalothrin has more durability than deltamethrin Conclusions:We established that lambdacyhalothrin can be used into control and elimination setting of malaria with two rounds of spray at an interval of 3-4 months in south of Iran.

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“…The optical isomers of S-315l were hydrolysed to give the corresponding isomers of DCPI, which were then derivatized to dia- four optical isomers of S-3151 was determined by their corresponding peak area ratios in the (1) chromatogram. In the process of the esteri- stereoisomers by esterification with d-or /-2-octanol and resolved by GLC like those of the esters of chrysathemumic acid.…”

Section: Resultsmentioning

confidence: 99%

Gas-liquid Chromatographic Determination of a New Pyrethroid, Permethrin(S–3151) and Its Optical Isomers

Horiba

Kobayashi

Murano

1977

Agricultural and Biological Chemistry

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Gas-liquid chromatographic (GLC) methods were developed for the determination of 3 -phenoxybenzyl dl-cis, trans-3 -(2,2-dichlorovinyl)-2,2-dimethy1cyc!opropane-l-carboxyla te (S-3151, permethrin or Exmin ®), its geometrical and optical isomers and its impurities. dl-Trans and dl-cis isomers were separated from each other on a 2 % LAC-2R-446 column and determined by using dioctyl phthalate as an internal standard, and the overall content of 8-3151 was obtained by the sum of them. Optical isomers, namely, d-cis, I-cis, d-trans and I-trans forms were hydrolysed to the corresponding acids, which were derivatized to the diastereoisomer esters with d-or 1-2-octanol and separated from one another on a 10% silicone DC QF-l column. The optical isomer ratios were determined by the peak area ratios. The impurities of 8-3151 were identified by mass spectrometer combined with GLC on a 2 % PEG-20 M column and they were determined by programmed temperature GLe.

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Potent Pyrethroid Insecticides from Modified Cyclopropane Acids

Cited by 85 publications

References 9 publications

Degradation, metabolism and toxicity of synthetic pyrethroids.

Degradation, metabolism and toxicity of synthetic pyrethroids.

The Field Practices of Lambdacyhalothrin and Deltamethrin Insecticides Against Adult Mosquitoes of Anopheles stephensi as the Main Vector of Malaria: Residual Effects

Gas-liquid Chromatographic Determination of a New Pyrethroid, Permethrin(S–3151) and Its Optical Isomers

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