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PubMed2000

The production of pyrethrins by plant cell and tissue cultures of Chrysanthemum cinerariaefolium and Tagetes species.

Pyrethrins, the most economically important natural insecticide, comprise a group of six closely related monoterpene esters. The industrial production is based on their extraction from Chrysanthemum cinerariaefolium (Pyrethrum) capitula. The world production of natural pyrethrins still falls short of global market demand stimulating the research in in vitro production as an alternative to conventional cultivation methods. The different biotechnological alternatives such as callus cultures, shoot and root cultures, plant cell suspension cultures, and bioconversion of precursors by means of enzymatic synthesis or genetically engineered microorganisms, as well as the progress achieved in methods for the identification and quantitation of insecticidal compounds have been reviewed. Although technology for plant cell culture exists, industrial applications have, to date, been limited due to both the low economical viability and technological feasibility at large scale. Bioconversion of readily available precursors looks more attractive, but more research is needed before this technology is used for the industrial production of pyrethrins.

Asteraceae↗

PubMedDate not supplied

Treatment of infestation with Phthirus pubis: comparative efficacies of synergized pyrethrins and gamma-benzene hexachloride.

In recent years there has been a steady increase in the incidence of infestation with Phthirus pubis, a sexually transmitted louse. A recently introduced nonprescription liquid pediculicide, whose major ingredient is 0.3% pyrethrins synergized by 3.0% piperonyl butoxide (RiD), was compared for efficacy and safety with a prescription-only pediculicidal lotion whose major ingredient is 1% gamma-benzene hexachloride (Kwell). Thirty adult man and women with P. pubis infestation were assigned randomly to treatment with either the synergized pyrethrins or gamma-benzene hexachloride. A single 10-min application of the synergized-pyrethrin liquid produced the same results as a single 12-hr application of the gamma-benze hexachloride lotion: total eradication of adult lice and nymphs, cessation of pruritus, and no treatment-induced side effect. A follow-up visit a week after treatment verified all eradications.

Adolescent↗

PubMed1990

Filth fly resistance to pyrethrins associated with automated spray equipment in poultry houses.

Resistance to pyrethrins plus piperonyl butoxide (PB) in a population of Fannia canicularis (L.) (BR strain) at a broiler-breeder facility was determined (in F2 laboratory generation) to be 109.1-fold the median lethal dose (LD50), apparently having been influenced by twice-daily treatments with automatic spray equipment during the previous 2 years. By contrast, resistance was only 12-fold the normal LD50 in a population of Musca domestica L. (DH strain) at an egg-production facility that was subjected during a comparable period to treatments twice per week with synergized pyrethrins with the identical automatic pyrethrin-spray system. The automated application of a nonpersistent chemical at frequent intervals, obviously, provides continuity of selection pressure leading to high levels of resistance. Other factors such as enclosed poultry housing and the elimination of refugia have also contributed to the enhancement of resistance. The resistance level in Strain BR regressed to 31.7-fold after remaining unselected for an additional generation in the laboratory. Other bioassays on the F2 generation revealed limited resistance toward permethrin of 3.7-fold the normal LD50.

Aerosols↗

PubMed1985

Use of a pyrethrin larvicide to control Culicoides variipennis (Diptera: Ceratopogonidae) in an alkaline lake.

Laboratory bioassays with Culicoides variipennis larvae from Borax Lake, CA, indicated an LC90 of 16.8 ppb for pyrethrins at 23 degrees C. A field test in a pond adjoining the lake reduced adult C. variipennis emergence greater than 99% for over 30 days after treatment at a rate of 131 ppb pyrethrins. Further small scale field tests indicated that C. variipennis could be controlled in the lake at a rate of 701 g/ha pyrethrins applied as a peripheral treatment. The first lake treatment resulted in a 99.3% decrease in the density of C. variipennis larvae along the shoreline. Four treatments resulted in a 98.5% decrease from non-treatment years in the number of adult cumulative insect-days during May and June.

Animals↗

PubMed1982

Composite sampling in the determination of pyrethrins in fruit samples.

A residue method is described for measuring up to 6 naturally occurring pyrethrins in several varieties of fruits. Fresh samples are extracted into acetone, partitioned between water and hexane-dichloro-methane, and cleaned up by adsorption on a Florisil column followed by elution with acetone-hexane (15 + 85). Residues are detected and quantitated by gas chromatography with electron capture detection. Detection limits for single 10 g samples are about 10-30 ng/g. The method was applied to a survey of pyrethrins in fruit samples. Because of the high tolerance (1 ppm) allowed for pyrethrins, the expected low incidence, and the low detection limits of the method, composite samples (up to 5-6) of fruit were used to quickly determine residue levels. This procedure allowed 130 samples to be processed in the time normally needed for 30-40. Provided the above conditions can be met, composite sampling is proposed as an attractive approach to data gathering in pesticide residue analysis.

Chromatography, Gas↗

PubMed1991

Trap perches to assess the activity of pyrethrins against the poultry red mite Dermanyssus gallinae in cage birds.

Trap perches were utilised to quantify mite recoveries during efficacy tests of pyrethrin formulations against experimental infestations of Dermanyssus gallinae (De Geer, 1778) in budgerigars and pigeons, and to monitor mite recoveries from untreated canaries. Pyrethrins applied topically before infestation significantly reduced the mean numbers of poultry red mites found in both budgerigar and pigeon trap perches, over those in untreated controls (P = less than 0.01). In untreated control budgerigars and pigeons, and in untreated canaries, the percentage recoveries after 48 h were 12.6 +/- 1.6, 4.1 +/- 1.9, and 32.6 +/- 1.6%, respectively (geometric mean +/- SD), and the blood engorgements rates were 71.5 +/- 1.7, 11.9 +/- 5.1, and 90.1 +/- 1.0% respectively. The recovery in trap perches of mites from canaries declined exponentially; 85% of the cumulative total recovered was collected 24 h after infestation, but small numbers were recovered daily up to 96 h (limit of observation). The use of the trap perches is discussed as a way of assessing the efficacy of acaricides, and as a laboratory tool in studies on mite aggregation behaviour or immune responses to mite infestation.

Administration, Topical↗

PubMed1996

Chromatographic methods for the determination of pyrethrin and pyrethroid pesticide residues in crops, foods and environmental samples.

An overview is given of current progress in the analysis of pyrethrin and pyrethroid pesticide residues in crops, foods and environmental matrices. Extraction and clean-up are considered as the sample pretreatment prior to the determination. The conventional procedures (liquid-liquid partition and column chromatography) as well as the newly developed methods (solid-phase extraction, supercritical fluid extraction) are reviewed. GLC, HPLC and TLC chromatographic methods as the final determination of individual pyrethrin and pyrethroid residues and multi-residue, the enantiomer and diastereomer separation as well as the GC-MS confirmation are discussed and summarized in tabular form.

Chromatography↗

PubMed1997

Residue levels of pyrethrins and piperonyl butoxide in soil and runoff water.

Simultaneous analysis of pyrethrins (Py-I and Py-II) and piperonyl butoxide (PBO) in soil and runoff water samples following field application of a new pyrethrum formulation containing pyrethrins (Py's) and PBO is described. Residues of total Py's and PBO were extracted from soil samples using hexane-acetone (9:1). A solid phase extraction (SPE) column containing C18-octadecyl bonded silica was used to separate Py's and PBO residues from runoff water. Residues in soil and water were quantitated by high performance liquid chromatography (HPLC) equipped with C18-column and a UV detector. Concentration of Py-II in soil was 100 times higher than that of Py-I 1 h following treatment and 9.6 times higher than Py-I in runoff surface water 11 days following treatment. Results indicated that Py's are non-persistent in soil (even though lipophillic) and water when applied at the recommended rate of 6 lbs (5.31 g A.I.) per acre. There was a consistent decrease in total Py's residues as time after spraying increased. Py's residues in soil decreased from 0.91 to 0.11 ppm 4 days following treatment and one month after treatment only 0.002 ppm were detected. The highest concentration of Py's in runoff water was 36.09 ng/liter following the first rainfall (11 days following treatment). PBO initial residues detected in soil samples were low (0.84 microgram/g soil) while no residues of PBO were detected in runoff water.

Fresh Water↗

PubMed1994

Resistance to pyrethrins in the German cockroach: inheritance and gene-frequency estimates in field-collected populations (Dictyoptera: Blattellidae).

Pyrethrins resistance was assessed genetically in the German cockroach, Blattella germanica (L.), by conventional crossing experiments. It is inherited as a simple, autosomal, incompletely dominant, trait. By manipulating the test procedure, the susceptible homozygote was clearly identified, allowing gene frequency estimates to be made using the Hardy-Weinburg equilibrium expression. Gene frequencies were estimated for four susceptible and 16 resistant field-collected populations. Values ranged from 0.10 to 0.18 for the susceptible strains, and from 0.34 to > 0.90 for the resistant strains. Changes in gene frequency over time for several resistant strains were not significant. The results are discussed from the standpoints of their effects on cockroach control and the stability of pyrethrins resistance even during extended periods with no selection pressure.

Animals↗

PubMed2006

Efficacy and tolerability of a new synergized pyrethrins thermofobic foam in comparison with benzyl benzoate in the treatment of scabies in convicts: the ISAC study (Studio Della scabbia in ambiente carcerario).

BACKGROUND: Scabies is a very common skin infection in convicts. The SIMSPE Society (Società Italiana di Medicina e Sanità Penitenziaria) has organized and conducted a multicentre, randomized, comparative, parallel group, investigator-blinded trial to evaluate the efficacy and tolerability of synergized pyrethrins foam (PF) in comparison with benzyl benzoate (BB) lotion. METHODS: A total of 240 convicted patients, enrolled in eight National Jail Institutions, with a clinical diagnosis of scabies, were treated with PF (n = 120) for three consecutive days or BB (n = 120) for five consecutive days. Primary study endpoints were the clinical cure rate and the local tolerability. Secondary endpoints were clinical evolution of scabietic lesions and itching intensity. Study outcomes were assessed using appropriate semiquantitative scores at baseline and after 2 and 4 weeks. A second treatment cycle was applied if after 2 weeks the patient was not judged clinically cured. RESULTS: At week 2, a total of 75% (95% CI: 66-82%) and 71% (95% CI: 62-78%) of patients showed a complete clinical cure rate in the PF and BB groups, respectively. At week 4, the percentage of totally cured patients increased up to 95% (95% CI: 89-97%) and 91% (95% CI: 83-94%) in the PF and BB groups, respectively (P = NS between groups). At week 4, 5% in the PF group and 9% in the BB group complained of itching. Burning and irritation after treatment applications were more common in the BB group in comparison with the PF group. The tolerability score was better in the PF group in comparison with to BB group (2.9 vs. 2.2; P = 0.0001). A total of 95% of patients in the PV group had a good tolerability score (i.e. = 3) in comparison with 41% in the BB group. CONCLUSION: Our results show that a 3-day treatment with pyrethrins thermofobic foam is at least as effective as a 5-day treatment with benzyl benzoate lotion in convicted subjects with scabies. The foam formulation is better tolerated than the benzyl benzoate lotion.

Administration, Topical↗

PubMed1994

Fatality associated with inhalation of a pyrethrin shampoo.

A fatality associated with the inhalational exposure to a pyrethrin insecticide is described. Death was attributed to sudden irreversible bronchospasm. While less severe allergic reactions have been reported, this is the first death associated with pyrethrin inhalation.

Administration, Inhalation↗

PubMed1999

Effects of ultra-low volume pyrethrin, malathion, and permethrin on nontarget invertebrates, sentinel mosquitoes, and mosquitofish in seasonally impounded wetlands.

Wildlife managers are concerned that insecticides used to control mosquitoes could suppress invertebrates on which wildlife feed. We assessed whether ultra-low volume (ULV) applications of pyrethrin, permethrin, and malathion for control of adult mosquitoes reduced macroinvertebrate abundance and biomass or killed mosquitofish in seasonal wetlands in California. Pyrethrin was applied over 3 seasonal wetlands on Sutter National Wildlife Refuge (NWR), and malathion or permethrin were each applied over 2 seasonal wetlands on the Colusa NWR. Three control wetlands were used per site. We measured aquatic macroinvertebrate abundance and biomass before and after insecticide application and compared the survival of mosquito larvae held in sentinel cages. At Colusa, we also used mosquitofish as sentinels, caged adult mosquitoes over the wetlands to test for pesticide efficacy and drift, and sampled night-flying insects using ultraviolet light traps. Results showed no detectable reductions in the abundance or biomass of aquatic macroinvertebrates in treated wetlands. Larval mosquitoes showed high survival in all areas. All adult mosquitoes died when caged over wetlands treated with malathion or permethrin, but all survived in controls. All mosquitofish survived. Flying insect abundance decreased after insecticide application in both treated and control wetlands but rebounded in 48 h. Results indicated that ULV applications of these insecticides to control adult mosquitoes are unlikely to have substantial effects on the aquatic insects or fish in seasonal wetlands.

Animals↗

PubMed2001

A case of pubic lice resistant to pyrethrins.

BACKGROUND: Effective therapeutic protocols for the treatment of pubic lice include application of approved insecticidal products to all body and scalp hair, retreatment at seven days, and use of mechanical removal of lice and eggs. OBJECTIVE: We report here infection with pubic lice in a 43 year old male in Australia which failed to be eradicated by adequate therapy with a pyrethrin and piperonyl butoxide product. DISCUSSION: Pubic lice collected from the case survived after exposure to the same product in vitro. The infestation was cured by use of 5% permethrin. This appears to be the first report of Pthirus pubis resistant to insecticides, in this case pyrethrins and their synergist, piperonyl butoxide.

Adult↗

PubMed1977

Separation and analysis of the pyrethrins by combined gas-liquid chromatography-chemical ionization mass spectrometry.

Pyrethrins, the 6 naturally occurring insecticidal esters of pyrethrum extract, were analyzed by combined gas-liquid chromatography-chemical ionization mass spectrometry. Separation was best on an OV-25 column with temperature programming; The chemical ionization mass spectra for the 6 esters as well as for the thermally isomerized pyrethrins I and II are reported and discussed. Using selective ion monitoring, a lower limit of detectability of all 6 esters was 114 ng of total extract injected on the column.

Chromatography, Gas↗

PubMed1988

Pyrethrins combined with piperonyl butoxide (RID) vs 1% permethrin (NIX) in the treatment of head lice.

In a randomized controlled trial, 58 subjects were treated for Pediculus humanus var capitis with either pyrethrins combined with piperonyl butoxide (RID, Pfizer Inc, New York) or 1% permethrin (NIX, Burroughs Wellcome Co, Research Triangle Park, NC); 31 subjects received RID and 27 subjects received NIX. Both products were applied according to manufacturer's directions so that NIX was applied only on the first visit and RID was applied on the first visit and again seven days later. After each treatment with a pediculicide, the comb supplied by the manufacturer was used to remove nits. Seven days after the initial visit, NIX was determined to be significantly better than RID for eradicating the lice infestation. Of the 27 subjects receiving NIX, 26 were live free vs 14 of the 31 RID-treated subjects. At day 14, there was no statistically significant difference in the treatments (27 of 27 NIX-treated vs 29 of 31 RID-treated subjects were lice free). The RID comb was superior to the NIX comb for nit removal. Both treatments were effective and well tolerated, and no subject experienced adverse reactions.

Adolescent↗

PubMed1994

Determination of traces of pyrethrins and piperonyl butoxide in biological material by high-performance liquid chromatography.

A liquid chromatographic method for the determination of pyrethrins and of the synergist piperonyl butoxide in human plasma after C18 solid-phase extraction is described. UV detection was found to be sensitive enough to determine concentrations far below the limit of toxicity. With respect to future investigations concerning studies in biological materials, a column-switching system for sample preparation was developed and compared with solid-phase extraction. Both methods show comparable limits of detection, but the column-switching technique has the advantage of fully automating the system.

Chromatography, High Pressure Liquid↗

PubMed2005

Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry.

A new developed gas chromatographic-high resolution mass spectrometric method for the sensitive simultaneous determination of trans-chrysanthemumdicarboxylic acid, cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylic acid, 3-phenoxybenzoic acid and 4-fluoro-3-phenoxybenzoic acid in human urine is presented. These metabolites are biomarkers for an exposure to pyrethrum, allethrin, resmethrin, phenothrin, tetramethrin, cyfluthrin, cypermethrin, deltamethrin or permethrin. Therefore, with the help of this method for the first time a complete assessment of exposure to pyrethroid and pyrethrin insecticides is possible. After acid hydrolysis and extraction with tert-butyl-methyl-ether the residue is derivatized with 1,1,1,3,3,3-hexafluoroisopropanol and analyzed by GC/HRMS in electron impact mode (detection limits < 0.1 microg/l) as well as in negative chemical ionization mode (detection limit < 0.05 microg/l urine).

Gas Chromatography-Mass Spectrometry↗

PubMed2000

Carbon-based quantitation of pyrethrins by supercritical-fluid chromatography.

All six insecticide active ingredients in pyrethrum extract were quantified by supercritical fluid chromatography and carbon calibration. Allethrin is a suitable reference compound for carbon calibration and pyrethrins calibrations. Carbon quantification in SFC is also applied to pyrethroids (phenothrin, permethrin, cypermethrin, fenvalerate and deltamethrin) and alkanes. Halogen substitution on pyrethroids requires halogens on the reference calibration compound. The method was applied to commercial extracts.

Alkanes↗