ACTIVITY: Insecticide (pyrethroid)

CAS Name: (2,3,5,6-tetrafluorophenyl)methyl (1R-trans)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Structure:

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Order No.	Title	Keywords	CAS Nos.
NTIS/OTS0543290-2 EPA/OTS; Doc #89970000165	1997 - SUPPORT: NAK 4455 - STUDY FOR CHRONIC TOXICITY AND CANCEROGENICITY IN WISTAR RATS (ADMINISTRATION IN DIET FOR 2 YEARS), WITH TSCA HLTH & SFTY STUDY CVR SHT DATED 5/8/97 BAYER AG	BAYER CORP (2,3,5,6-TETRAFLUOROPHENYL)- METHYL-(1R-TRANS)-3-(2,2- DICHLO* HEALTH EFFECTS CHRONIC TOXICITY COMBINED CHRONIC TOXICITY/CARCINOGENICITY MAMMALS RATS ORAL DIET	118712-89-3
NTIS/OTS0543287-1 EPA/OTS; Doc #89-950000175	1995 - SUPPORT: ASSESSMENT OF RESULTS OF SPECIFIC MOUSE AND RAT CHRONIC TOXICITY/ONCOGENICITY STUDIES OF NAK 4455, WITH COVER LETTER DATED 03/31/95 JELLINEK, SCHWARTZ & CONNOLLY	MILES INC NAK 4455 HEALTH EFFECTS CHRONIC TOXICITY COMBINED CHRONIC TOXICITY/CARCINOGENICITY MAMMALS RATS ORAL DIET CARCINOGENICITY MICE	118712-89-3
NTIS/OTS0543290-1 EPA/OTS; Doc #89-950000174	1995 - SUPPORT: ASSESSMENT OF COMBINED CHRONIC TOXICITY/ONCOGENICITY RAT AND MOUSE STUDIES OF NAK 4455, WITH COVER LETTER DATED 03/31/95 JELLINEK, SCHWARTZ & CONNOLLY	MILES INC NAK 4455 HEALTH EFFECTS CHRONIC TOXICITY COMBINED CHRONIC TOXICITY/CARCINOGENICITY MAMMALS RATS ORAL DIET CARCINOGENICITY MICE	118712-89-3

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15921213&query_hl=2 Am J Rhinol. 2005 Mar-Apr;19(2):141-51.   Genotoxic effects of pentachlorophenol, lindane, transfluthrin, cyfluthrin, and natural pyrethrum on human mucosal cells of the inferior and middle nasal conchae. Tisch M, Faulde MK, Maier H. Department of Otorhinolaryngology, Head and Neck Surgery, Bundeswehr Hospital, Ulm, Germany. BACKGROUND: Animal experiments and epidemiological studies suggest that pentachlorophenol (PCP) and gamma-hexachlorocyclohexane (lindane) should be classified as possible human carcinogens. In the past, both have had a variety of applications in the civilian and military sectors and in forestry. They have, e.g., been used to impregnate and treat uniforms and other fabrics and to control human lice. Animal experiments indicate that PCP in particular causes mutations and chromosome aberrations and thus DNA damage. Studies on whether or not this also applies to newer substances and especially to natural type I and type II pyrethroids still are not available. What is particularly lacking are data on the genotoxic effects of these substances on human target cells. Our study describes the genotoxic effects of PCP, lindane, transfluthrin, cyfluthrin, and natural pyrethrum on human mucosal cells of the inferior and middle nasal conchae. METHODS: Epithelial cells were isolated from nasal mucosa, which was removed in the surgical treatment of chronic sinusitis and nasal concha hyperplasia. After the cells had been tested for vitality using the trypan blue exclusion test, the short-term culture method was used. The material was incubated with PCP (0.3, 0.75, and 1.2 mmol), lindane (0.5, 0.75, and 1.0 mmol), transfluthrin (0.05, 0.1, 0.5, 0.75, and 1.0 mmol), cyfluthrin (0.05, 0.1, 0.5, 0.75, and 1.0 mmol), natural pyrethrum (0.001, 0.005, 0.01, 0.05, and 0.1 mmol), and N-methyl-N'-nitro-N-nitrosoguanidine for 60 minutes. Substance-induced DNA damage (single-strand and double-strand breaks) were determined using single-cell microgel electrophoresis. A fluorescence microscope was used together with an image processing system to analyze the results obtained. RESULTS: After exposure to all tested substances, a high percentage of the cells of the middle nasal concha in particular were found to have severely fragmented DNA as a result of strong genotoxic effects. Although the reaction of the cells of the inferior nasal concha was significantly less strong (p < 0.001), the tested substances were nevertheless found to have a notable genotoxic effect on these cells too. CONCLUSION: Our study strongly suggests that exposure to PCP, lindane, transfluthrin, cyfluthrin, and natural pyrethrum has a genotoxic effect on the epithelial cells of human nasal mucosa. In addition, we have shown that nasal structures differ in susceptibility to the various pesticides used in the tests. Thus, the study provides new evidence supporting the biological plausibility of PCP- and lindane-induced effects, thereby helping evaluate potential PCP- and lindane-induced mucous membrane carcinomas of these parts of the nose. In addition, our study shows that other substances that today are widely used for controlling pests have a considerable genotoxic effect on human target cells. The results obtained indicate the need for additional studies on the genotoxicity of these substances and their adverse effects on human health. PMID: 15921213 [PubMed - in process]

From Toxline at Toxnet PESTICIDE SCIENCE; 52 (1). 1998. 3-20. Research into fluorinated pyrethroid alcohols: An episode in the history of pyrethroid discovery. NAUMANN K Landwirtschaftszentrum Monheim, Bayer AG, D-51368 Leverkusen, Germany. BIOSIS COPYRIGHT: BIOL ABS. An account of pyrethroid research from 1975 to 1985 at Bayer AG is given. The exploitation of fluorine chemistry for this purpose led to increased activity of known 3-phenoxybenzyl pyrethroid esters and to the commercialization of the broad-spectrum insecticide cyfluthrin, the particularly tick-toxic flumethrin and the rapid-acting household insecticides fenfluthrin and transfluthrin. The last two constituted in 1976 a novel type of pyrethroid, based on polyfluorinated benzyl alcohols, off the mainstream of published pyrethroid research. Transfluthrin, the single isomer (1R)trans-permethric acid ester of 2,3,5,6-tetrafluorobenzyl alcohol has just been introduced to the market. The history of its discovery and structure-activity data as well as resistance considerations regarding cyfluthrin, are presented.

Report: Evaluation on: Transfluthrin Use as a Public Hygiene Insecticide. September 1997. Prepared by: the UK Health and Safety Executive, Biocides & Pesticides Assessment Unit, Magdalen House, Stanley Precinct, Bootle, Merseyside L20 3QZ. Available from: Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, Mallard House, Kings Pool, 3 Peasholme Green, York YO1 7PX. UK. Available at: http://www.pesticides.gov.uk/citizen/evaluations/165_confirm-box.htm

• Note from FAN: The following study seems promising (albeit that we are expected to be the unwitting repositories of industrial chemicals and pesticides). Of interest, transfluthrin is not registered for use in the US, yet it has been included in this study supported by US agencies. Also, according to the UK report, cited above, animal studies showed high levels of fluoride in the teeth and bone. - EC. From Toxline at Toxnet Fetal exposure to environmental toxins & infant outcome Year of Publication: 2002 Authors: OSTREA EMJR Author Address: EOSTREA@MED.WAYNE.EDU, HUTZEL HOSPITAL, 4707 ST ANTOINE BOULEVARD, DETROIT, MI 48201 Source: Crisp Data Base National Institutes of Health Supporting Agency: U.S. DEPT. OF HEALTH AND HUMAN SERVICES; PUBLIC HEALTH SERVICE; NATIONAL INSTITUTES OF HEALTH, NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT DESCRIPTION (provided by applicant): The exposure of pregnant women to environmental toxins is of major concern because of their potential harm on the fetus. However, the detection of fetal exposure to environmental toxins still remains a major challenge. We propose that meconium analysis is a promising tool to meet this challenge. Aims: (1) To compare the prevalence and amount of fetal exposure to environmental toxins through the analysis of meconium, cord blood and neonatal hair and to determine the degree of agreement among these three methods, (2) to determine the relationship between the prevalence and amount of maternal exposure to environmental toxins during pregnancy, as determined by serial analyses of maternal hair and blood, to the prevalence and amount of fetal exposure to environmental toxins as determined by meconium, cord blood and neonatal hair analyses, and (3) to compare adverse immediate (birth weight, length, head circumference, gestational age) and long term (postnatal growth and neurobehavioral development up to 2 yrs from enrollment) outcomes that are associated with antenatal exposure to environmental toxins as determined by maternal blood, maternal hair, meconium, cord blood and neonatal hair analyses. Study design: Pregnant women (n=750) will be recruited, at midgestation, from the Outpatient Clinic of the Bulacan Provincial Hospital, Philippines and their blood and hair will be obtained at the time of recruitment and at delivery. Umbilical cord blood, meconium and neonatal hair will also be obtained. The samples will be analyzed, by atomic absorption spectrometry, for lead, mercury and cadmium and by gas chromatography/mass spectrometry for the following pesticides and their metabolites: propoxur, transfluthrin, Malathion, DDT, chlorpyrifos, bioallethrin, pretilachlor, lindane, cyfluthrin and cypermethrin. Pertinent maternal and infant data will be obtained after birth. The infants will be subsequently followed up at scheduled intervals for 2 years, to study their physical growth and neurobehavioral development using a battery of tests. Data analysis: The relationship between the presence/amount of environmental toxins in meconium, maternal blood, maternal hair, cord blood or neonatal hair to the immediate and two year outcome in the infants will be studied, while controlling for potential confounders. The presence/amount of environmental toxins in maternal blood, hair, cord blood, meconium and neonatal hair will be also evaluated to determine which substrate (s) provide(s) the best index of exposure for a given toxin. Expected benefits: Meconium analysis may provide a powerful tool to study the prevalence and degree of fetal exposure to environmental toxins and its associated adverse effects. This project can also serve as a model for the study of environmental pollutant problems during pregnancy at a local, national or global level.

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15018801

J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 5;802(2):371-6.
 
Electron ionization gas chromatography-mass spectrometric determination of residues of thirteen pyrethroid insecticides in whole blood.

Ramesh A, Ravi PE.

Department of Analytical Chemistry, Mass Spectrometry Division, International Institute of Biotechnology and Toxicology-IIBAT, Padappai, Chennai 601301, Tamil Nadu, India. raamesh_a@hotmail.com

A new rapid and sensitive electron ionization gas chromatography-mass spectrometry method in selective ion monitoring mode (SIM) was developed for the determination of l3 synthetic pyrethroid insecticide molecules and their stereo isomers in whole blood. The pyrethroid insecticides investigated are allethrin, bifenthrin, cypermethrin, cyphonothrin, cyfluthrin, lambda-cyhalothrin, deltamethrin, fenvalerate, fenpropathrin, imiprothrin, permethrin, prallethrin and transfluthrin. The residues of pyrethroids are extracted from the whole blood using hexane and acetone mixture (80 + 20%) as solvent. All the pyrethroid residues were separated by using a gas chromatography-mass spectrometry operated in electron ionization mode and quantified in selective ion monitoring mode. The method can detect the residues of different pyrethroids down to the level 0.05-2 ng/ml. Recovery experiments conducted in whole blood samples at the fortification level 1-1000 ng/ml showed 91-103% recovery. The applications of the analytical method for the determination of pyrethroid residues in real samples were tested by analyzing 45 human blood samples collected from the population exposed continuously to different pyrethroid based formulations. The results are confirmed by spiking the known quantity of pyrethroids and subsequently their positive detection.

PMID: 15018801 [PubMed - indexed for MEDLINE]

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http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12243228&dopt=Abstract

Med Vet Entomol. 2002 Sep;16(3):277-84.
 
Personal protection against mosquitoes in Dar es Salaam, Tanzania, by using a kerosene oil lamp to vaporize transfluthrin.

Pate HV, Line JD, Keto AJ, Miller JE.

Department of Infectious and Tropical Diseases, London School of Hygiene and Tropical Medicine, UK. helen.pates@lshtm.ac.uk

The effectiveness of a cheap and easy method of household protection against Culex quinquefasciatus Say and other mosquitoes (Diptera: Culicidae) was investigated in Dar es Salaam, Tanzania. Kerosene-burning lamps (korobois) were modified to heat and vaporize transfluthrin, a volatile pyrethroid insecticide. When transfluthrin was added to fuel of the lamp, protection against biting was poor unless a very high concentration of insecticide was used. A modified lamp (= vaporizing koroboi) was designed to overcome this problem by mixing the insecticide with vegetable oil and heating it to 120 degrees C in a tin held just above the flame. The concentration of 0.1% transfluthrin in vegetable oil gave 50-75% reduction in biting, a similar degree of protection to that obtained from burning a mosquito coil containing a synthetic pyrethroid (0.25% d-allethrin) and significantly better protection than a locally bought coil (brand 'White Crane', probably containing DDT). Greater protection (consistently > 90%) was achieved with a higher concentration of transfluthrin (0.5%) in the vegetable oil. This modified lamp is simple, cheap and employs locally available technology. With further development, and due regard to inhalation toxicity of the vaporized materials, it may offer a more cost-effective alternative to a mosquito coil as a means of personal protection, and a useful complement to a net for the early part of the evening before bedtime.

Publication Types:
• Clinical Trial
PMID: 12243228 [PubMed - indexed for MEDLINE]

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http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11354726&dopt=Abstract

J Environ Monit 2001 Feb;3(2):191-3

Monitoring of allethrin, deltamethrin, esbiothrin, prallethrin and transfluthrin in air during the use of household mosquito repellents.

Ramesh A, Vijayalakshmi A.

Department of Pesticide Chemistry, Fredrick Institute of Plant Protection and Toxicology, Padappai-601 301, Kancheepuram District, Tamil Nadu, India. raamesh_a@hotmail.com

Three types of mosquito repellent [two different mosquito coils containing allethrin 0.1% w/w and transfluthrin 0.03% w/w, an aerosol sample containing a combination of two pyrethroid molecules (deltamethrin 0.02% w/w + allethrin 0.13% w/w) and two different mosquito mats containing esbiothrin 2.0% w/w and prallethrin 1.5% w/w as active ingredients] were individually subjected to use in a closed room. Air samples from the room were drawn at different time intervals (15, 30 and 45 min, and 1, 2, 4, 6 and 8 h) uniformly from three different positions in the room (top, middle and bottom) with the pyrethroid contents analysed using gas chromatography-electron capture detection (GC-ECD). Analysis of air samples showed maximum concentrations of the pyrethroid residues allethrin (0.0120 ppm), transfluthrin (0.0134 ppm), deltamethrin (0.0057 ppm), allethrin (0.080 ppm), esbiothrin (0.015 ppm) and prallethrin (0.0138 ppm) within 30-45 min of use. The drop in residue content was significant with time. At the end of a 6 h period, most of the residues had dissipated to below 0.0001 ppm. Further significant differences were observed in the residue contents tested at different points within the room. Studies were compared with the experimental results obtained when the mosquito repellents were tested with air circulation in the room.

PMID: 11354726 [PubMed - indexed for MEDLINE]

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