Abstracts
Flumethrin
CAS No. 69770-45-2

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ACTIVITY: Acaricide, Insecticide (pyrethroid)

CAS Name: cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate

Structure:


http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=11743771

J Agric Food Chem. 2001 Dec;49(12):5835-42.
 
Study of acaricide stability in honey. Characterization of amitraz degradation products in honey and beeswax.

Korta E, Bakkali A, Berrueta LA, Gallo B, Vicente F, Kilchenmann V, Bogdanov S.

Departamento de Quimica Analitica, Facultad de Ciencias, Universidad del Pais Vasco, P.O. Box 644, 48080 Bilbao, Spain.

A study on the possible degradation of amitraz, bromopropylate, coumaphos, chlordimeform, cymiazole, flumethrin, and tau-fluvalinate during the storage of honey was carried out by HPLC. Except amitraz, the other acaricides are stable in this medium for at least 9 months. Degradation studies of amitraz in honey and beeswax were carried out; the degradation products detected in both matrices were 2,4-dimethylphenylformamide (DMF) and N-(2,4-dimethylphenyl)-N'-methylformamidine (DPMF). The reaction rate constants and the half-lives of the amitraz degradation in honey and wax were calculated. Amitraz was nearly completely degraded within 1 day in beeswax and within 10 days in honey. When amitraz-spiked combs are recycled into new beeswax, DMF was found to be the principal degradation product left in pure wax.

PMID: 11743771 [PubMed - indexed for MEDLINE]


From Science Direct

Veterinary Parasitology, Volume 88, Issues 1-2 , 29 February 2000, Pages 79-92

Possible risk factors on Queensland dairy farms for acaricide resistance in cattle tick (Boophilus microplus)

N. N. Jonsson (a), D. G. Mayer (b) and P. E. Green (b)

a Department of Veterinary Clinical Studies, University of Glasgow Veterinary School, Bearsden Rd Glasgow G61 1QH, UK
b Department of Primary Industries, Queensland Animal Research Institute, Moorooka, Qld 4105, Australia

A case control study was carried out within a cross-sectional survey designed to investigate the management by Queensland dairy farmers of the cattle tick Boophilus microplus. Although 199 farmers were surveyed, data on acaricide resistance were only obtained from 66 farms. Multiple models were used to predict the probability of acaricide resistance associated with 30 putative risk factors. The region of the state in which the farm was located and the frequency of acaricide application were consistently associated with acaricide resistance. The risk of resistance to all synthetic pyrethroids (Parkhurst strain) was highest in Central Queensland and increased when more than five applications of acaricide were made in the previous year, when spray races were used and when buffalo fly treatments with a synthetic pyrethroid were applied frequently. The probability of resistance to amitraz (Ulam strain) was highest in Central Queensland, increased when more than five applications of acaricide were made in the previous year, and decreased on farms when a hand-spray apparatus was used to apply acaricides to cattle. The probability of resistance to flumethrin (Lamington strain) was highest in the Wide Bay-Burnett region.


From Science Direct

Talanta, Volume 52, Issue 2 , 21 June 2000, Pages 169-180

Study of the degradation products of bromopropylate, chlordimeform, coumaphos, cymiazole, flumethrin and tau-fluvalinate in aqueous media

E. Corta (a), A. Bakkali (a), A. Barranco (a), L. A. Berrueta (a), B. Gallo (a), F. Vicente (a) and S. Bogdanov (b)

a Departamento de Química Analítica, Facultad de Ciencias, Universidad del País Vasco, P.O. Box 644, 48080 Bilbao, Spain
b Apicultural Department, Federal Dairy Research Institute, CH-3092 Liebefeld, Switzerland

Degradation processes of bromopropylate, coumaphos, chlordimeform, cymiazole, flumethrin and fluvalinate in aqueous media have been studied by HPLC. Cymiazole is stable at any tested pH (1–11), while bromopropylate, flumethrin and coumaphos are unstable at basic pH and chlordimeform and fluvalinate in neutral and basic media. The main degradation products have been identified by GC-MS. The reaction rate constants and half-lives were calculated and the effect of co-solvents on the rate and product profile was studied.


From Toxline at Toxnet

ACTA ALIMENTARIA; 28 (1). 1999. 85-94.

Determination and control of bee-acaricide flumethrin in honey and beewax.

SZERLETICS-TURI M

"Fodor Jozsef" National Center of Public Health, National Institute of Food Hygiene and Nutrition, Gyali ut 3/a, H-1097, Budapest, Hungary.

BIOSIS COPYRIGHT: BIOL ABS. In the last decades considerable economic damages were caused by Varroa mite in European and also in Hungarian apiaries. For the control fumigant strips, solutions and aerosols containing acaricide active ingredients were introduced. Plastic strips impregnated with synthetic pyrethroids show a high efficacy against these mites. The long-term (2-6 weeks) treatment, however, increases the problem of residues in honey and honeycomb. An analytical method was introduced in Hungary for the determinati [abstract truncated]


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.


From Toxline at Toxnet

Pesticide residues in food - 1996. Toxicological evaluations (1997) pp 141-59

Flumethrin

FAO and WHO working groups

Levels that cause no toxic effect. Rat: 10 ppm, equal to 0.7 mg/kg bw per day (13- and 15-week studies of toxicity); 5 ppm, equal to 0.36 mg/kg bw per day (two-generation study of reproductive toxicity); 0.5 mg/kg bw per day (maternal toxicity in a study of developmental toxicity). Rabbit: 1.7 mg/kg bw per day (maternal and fetal toxicity in a study of developmental toxicity). Dog: 25 ppm, equal to 0.88 mg/kg bw per day (13-week study of toxicity). Estimate of acceptable daily intake for humans 0-0.004 mg/kg bw.


From Toxline at Toxnet

Teratog Carcinog Mutagen 1996;16(1):37-48

Evaluation of the genotoxic potential of flumethrin in mouse bone marrow by chromosomal analysis and micronucleus test.

Nakano E, Rabello-Gay MN, Pereira CA

Laboratäorio de Biologia Celular, Instituto Butantan, S~ao Paulo, Brazil.

The genotoxic potential of the pyrethroid flumethrin was evaluated by using the combined protocol of metaphase analysis and micronucleus test in vivo in mouse bone marrow. The dermal route was tested in a single treatment and the intraperitoneal (i.p.) route in a single and a multiple treatment. Flumethrin showed a cytotoxic effect on both myelopoiesis and erythropoiesis, as evidenced by a reduction in the mitotic index and in polychromatic erythrocyte values. An increase in the frequency of gaps after the dermal exposure and of breaks only at the highest dose tested in the i.p. treatment indicates a weak clastogenic potential of the compound. A significant increase in the frequency of micronucleated polychromatic erythrocytes was observed after single and multiple i.p. treatments. In the latter, the induction of micronuclei was highly significant but not accompanied by an increase in breaks. This may indicate that the clastogenic effect might not account by itself for the induction of micronuclei, which could also have arisen from an aneugenic potential of flumethrin.

Note from FAN:
Myelopoiesis: Formation of MYELOID CELLS from the pluripotent HEMATOPOIETIC STEM CELLS in the BONE MARROW via MYELOID STEM CELLS. Myelopoiesis generally refers to the production of leukocytes in blood, such as MONOCYTES and GRANULOCYTES. This process also produces precusor cells for MACROPHAGE and DENDRITIC CELLS found in the lymphoid tissue. Ref: http://fred.hmc.psu.edu/ds/retrieve/fred/meshdescriptor/D038042
Erythropoiesis is the development of mature red blood cells (erythrocytes).

The above paper was abstracted in Food and Chemical Toxicology, Volume 34, Issue 10, October 1996, Page 1021 :

Flumethrin genotoxicity. Flumethrin, a synthetic pyrethroid insecticide, tested as the technical product Bayticol 60%, induced chromosomal damage in the bone marrow cells when administered to mice by intraperitoneal injection (Nakano et al., Teratogenesis, Carcinogenesis and Mutagenesis 1996, 16, 37).


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7747277&dopt=Abstract

Toxicol Appl Pharmacol 1995 May;132(1):14-8
Effects of flumethrin on hepatic drug-metabolizing enzymes and antipyrine disposition in rats.

Anadon A, Martinez-Larranaga MR, Diaz MJ, Bringas P, Fernandez MC, Martinez MA, Fernandez-Cruz ML.

Department of Toxicology, Faculty of Veterinary Medicine, Universidad Complutense de Madrid, Spain.

The effects of repeated exposure to the pyrethroid insecticide flumethrin (40 mg/kg intraperitoneally once a day for 6 days) on the activity of cytochrome P450-dependent monooxygenases and UDP-glucuronosyltransferase as well as on antipyrine disposition were investigated in male Wistar rats. Pretreatment with flumethrin decreased the activities of NADPH-cytochrome c reductase (38%), aniline hydroxylase (53%), aminopyrine N-demethylase (54%), and UDP-glucuronosyltransferase (34%), and the content of cytochrome P450 (36%) in hepatic microsomes. Total plasma clearance of antipyrine was decreased by flumethrin pretreatment (54%), while the elimination half-life at beta phase and the mean residence time of antipyrine were increased (96 and 88%, respectively). Urinary excretion of norantipyrine, 4-hydroxyantipyrine, and 3-hydroxymethylantipyrine was decreased by 60, 38, and 33%, respectively, in the 96 hr after flumethrin treatment. In addition, the rate constants for formation of each of these metabolites were decreased by an average of approximately 74%. These findings provide evidence that flumethrin exposure diminishes hepatic enzyme levels and catalytic activities of monooxygenase systems as well as oxidative metabolism of antipyrine.


PMID: 7747277 [PubMed - indexed for MEDLINE]

http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9004471&dopt=Abstract
 
Vet Hum Toxicol 1997 Feb;39(1):6-8
 
Pyrethroid residues in milk and blood of dairy cows following single topical applications.

Bissacot DZ, Vassilieff I.

Center for Toxicological Assistance (CEATOX), Institute of Biosciences, UNESP, Botucatu, SP, Brazil.

The presence of the pyrethroid insecticides flumethrin, deltamethrin, cypermethrin and cyhalothrin in milk and blood of 10 cows was determined after single dermal applications of recommended doses. Milk and blood samples were collected every 7 days over a 35-d period and analyzed by high-performance liquid chromatography. The highest residues in milk were found on day 28 for flumethrin and day 1 for deltamethrin, cypermethrin and cyhalothrin, while in blood the highest concentrations were present on day 28 for flumethrin and deltamethrin, the first day for cypermethrin, and day 14 for cyhalothrin.


PMID: 9004471 [PubMed - indexed for MEDLINE]

From Toxline at Toxnet

PESTIC BIOCHEM PHYSIOL; 25 (2). 1986. 176-187.

Action of pyrethroids on a nerve-muscle preparation of the clawed frog, Xenopus laevis.

RUIGT G SF, VAN DEN BERCKEN J

Dep. Veterinary Pharmacol., Pharmacy Toxicol. Univ. Utrecht, P.O. Box 80176, 3508 TD Utrecht, Netherlands.

BIOSIS COPYRIGHT: BIOL ABS. The effects of a range of pyrethroids on end-plate potentials and muscle action potentials were studied in the pectoralis nerve-muscle preparation of the clawed frog, Xenopus laevis. The non-cyano pyrethroids allethrin, cismethrin, bioresmethrin, and 1R-cisphenothrin caused moderate presynaptic repetitive activity only, resulting in the occurrence of multiple end-plate potentials (epps). Trains of repetitive muscle action potentials without presynaptic repetitive activity were observed after the alpha-ethynyl pyrethroid S-5655 and after the alpha-cyano pyrethroids cypermethrin, deltamethrin, FCR 1272 [Cyfluthrin], and FCR 2769 [Fenfluthrin]. An intermediate group of pyrethroids consisting of the non-cyano compounds 1R-permethrin, des-cyano-deltamethrin, NAK 1901 and NAK 1963, and the alpha-cyano pyrethroids cyphenothrin and fenvalerate caused both types of effect. The insecticidally inactive S-enantiomers of permethrin had no effect on the nerve-muscle preparation. Trains of repetitive action pot [truncated abstract]

CAS Registry Numbers:
69770-45-2 - Flumethrin
69770-45-2 - Flumethrin

68359-37-5 - Cyfluthrin
57731-67-6 - Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, ethynyl(3-phenoxyphenyl)methyl ester
54774-45-7 - (+)-cis-Permethrin
52918-63-5 - Deltamethrin
52315-07-8 - Cypermethrin
51630-58-1 - Pydrin
39515-40-7 - Cyphenothrin
35764-59-1 - Cismethrin
28434-01-7 - Bioresmethrin
584-79-2 - Bioallethrin


 

 
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