Abstracts
Flucythrinate
CAS No. 70124-77-5

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Adverse Effects

ACTIVITY: Acaricide; Insecticide (pyrethroid)

CAS Name: cyano(3-phenoxyphenyl)methyl (S)-4-(difluoromethoxy)-?-(1-methylethyl)benzeneacetate

Structure:


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7903603&dopt=Abstract

Carcinogenesis 1993 Dec;14(12):2531-5

Enhancement of altered hepatic foci in rat liver and inhibition of intercellular communication in vitro by the pyrethroid insecticides fenvalerate, flucythrinate and cypermethrin.

Hemming H, Flodstrom S, Warngard L.

Institute of Environmental Medicine, Karolinska Institutet, Stockholm, Sweden.

Male Sprague-Dawley rats dosed with N-nitrosodiethylamine (NDEA) 24 h after two-thirds partial hepatectomy were treated with the pyrethroid insecticides fenvalerate, flucythrinate or cypermethrin in the diet for 20 weeks. Altered hepatic foci were analyzed by quantitative stereology from paraffin-embedded sections stained for gamma-glutamyltranspeptidase (GGT) or glutathione S-transferase P (GST-P). The present results demonstrate that the pyrethroids tested all enhance the development of NDEA-initiated, GGT-positive foci in rat liver at non-hepatotoxic doses. On the contrary, the volume fractions of GST-P-positive foci were not elevated as compared to the control group. The three pyrethroids tested all inhibited the transfer of Lucifer Yellow CH between WB-F344 rat liver epithelial cells in culture, supporting the increase of GGT-positive foci and suggesting that these substances can act as tumour promoters. The discrepancy between the results from analyses using GGT or GST-P as markers emphasizes the importance of understanding the mechanism underlying the expression of different markers for preneoplastic lesions and the importance of such effects in tumour promotion.

PMID: 7903603 [PubMed - indexed for MEDLINE]


From Toxline at Toxnet

Cell Biology and Toxicology, Vol. 5, No. 1, pages 67-75, 27 references, 1989

Effects of Tetradecanoyl Phorbol Acetate, Pyrethroids and DDT in the V79

Warngard L, Flodstrom S

Department of Toxicology, Karolinska Institute, Stockholm, Sweden.

The effects of the pyrethroids flucythrinate (70124775), cyfluthrin (68359375), bioallethrin (584792) and resmethrin (10453868) were compared with the effects of tetradecanoyl-phorbol-acetate (TPA) and DDT on metabolic cooperation between Chinese-hamster-V79 cells to determine if pyrethroid structure was associated with ability to inhibit intercellular communication. Addition of flucythrinate (structurally related to fenvalerate and DDT) to cocultures of 6-thioguanine resistant cells and 6-thioguanine sensitive cells significantly increased mutant cell recovery, indicating inhibition of intercellular communication; other tested pyrethroids produced no such effect. Addition of TPA, together with increasing doses of flucythrinate or fenvalerate, produced a synergistic response. Various combinations of fenvalerate, flucythrinate, and DDT exposure indicated additive responses. The authors conclude that flucythrinate inhibits intercellular communication and that the p-substituted phenyl group may play an important role; there appear to be different pathways of action for TPA and the halogenated insecticides investigated in this study.


Available from The National Technical Information Service (NTIS)
- at http://www.ntis.gov/
Order No. Title Authors Abstract

NTIS/PB91-115931

47p


1989 -
Comparative Toxicology of the Pyrethroid Insecticides.

Bradbury SP, Coats JR

Environmental Research Lab.-Duluth, MN.
Iowa State Univ., Ames. Dept. of Entomology.

Synthetic pyrethroid insecticides are photostable analogs of the natural pyrethrins of botanical origin. Their structures range from very similar to the original (e.g., allethrin) to highly dissimilar compounds (e.g., flucythrinate). Directed synthesis by groups in Japan (Sumitomo Chemical Co.) and England (NRDC) resulted in very potent insecticides and a commercial success for the synthetic pyrethroids. (Copyright (c) 1989 by Springer-Verlag New York Inc.) Journal article. Pub. in Reviews of Environmental Contamination and Toxicology, v108 1989. Prepared in cooperation with Iowa State Univ., Ames. Dept. of Entomology.

NTIS/PB89-109292

13 p


1987 -
Effects of Type I and II Pyrethroids on Motor Activity and the Acoustic Startle Response in the Rat (Journal Version).

Crofton KM, Reiter LW

Health Effects Research Lab., Research Triangle Park, NC. Neurotoxicology Div.

Two behavioral tests, locomotor activity and the acoustic startle response (ASR), were utilized to separate the behavioral actions of Type I and II pyrethroids using permethrin, RU11679, cypermethrin, RU26607, fenvalerate, cyfluthrin, flucythrinate, fluvalinate and p,p'-DDT. Dosage-effect functions for all compounds were determined for both figure-8 maze activity and the ASR in the rat. All compounds were administered po in 1 ml/kg corn oil 1.5 - 3 hr prior to testing. The Type I compounds permethrin RU11679, along with p,p'-DDT, increased amplitude and had no effect on latency to onset of the ASR. In contrast, the Type II pyrethroids cypermethrin, cyfluthrin, and flucythrinate decreased amplitude and increased the latency to onset the ASR. Fenvalerate increased the amplitude, had no effect on latency, but unlike the other compounds tested, increased ASR sensitization. Fluvalinate had no effect on any measure of the ASR. The data provide further evidence of the differences between the in vivo

NTIS/PB85-104933

Pub. in Environmental Pollution (Series A) 35, p353-365 1984.

15 p

1984 - Toxicity of Flucythrinate to Gammarus lacustris (Amphipoda), Pteronarcys dorsata (Plecoptera) and Brachycentrus americanus (Trichoptera): Importance of Exposure Duration.

Anderson RL, Shubat P

Environmental Research Lab.-Duluth, MN.
Wisconsin Univ.-Superior. Center for Lake Superior Environmental Studies.

he effect of the synthetic pyrethroid flucythrinate on three non-target invertebrates was evaluated using continual and short-time exposure methods. Both methods show toxic action at measured concentrations 0.100 micrograms/litre. The use of both approaches pointed toward the importance of exposure time in hazard assessment. Exposures for a short time followed by an extended observation period in insecticide-free water show that a lethal exposure can occur in less time than estimated from continually exposed animals. For example, continually exposed Gammarus lacustris had a 72 h LC50 of 0.12 micrograms/litre. However, exposure for only 17.6 h at 0.12 micrograms/litre will kill 50% of the exposed animals during an extended observation time. The use of both approaches can also provide insights into minimum exposure times for each test concentration, and the possibility of post-exposure mortality. Journal article, Prepared in cooperation with Wisconsin Univ.-Superior. Center for Lake Superior En

 

Toxicology Letters; Volume 88 , October 1996, Pages 23-24

An in vitro sciatic nerve preparation for the evaluation of pyrethroid neurotoxicity and the possible assessment of organophosphate-induced neuropathy

G. Theophilidisa

Aristotle University of Thessaloniki, Laboratory of Animal Physiology, Department of Zoology Thessaloniki, Macedonia Greece

The neurotoxic action of six pyrethroid insecticides has been validated using an in vitro method. The method is based on a recording chambers designed in a such way that a large part of the nerve, can easily be exposed to various drugs. The main advantage of the method is that it permits continuous, stable recordings of the evoked compound action potential in the sciatic nerve of the frog for approximately three days (70 h to 80 h) and 8 to 10 h for the rat. The sciatic nerve was exposed to pyrethroids for 30 min. and from the plots of the amplitude of the compound action potential vs. time it was possible to estimate, for each compound, the minimum effective concentration which is required to reduce the amplitude of the compound action potential to 50% of its control value (mEC50). Using this parameter four pyrethroids were classified according to their relative potencies as follows: flucythrinate > deltamethrin > fluvalinate >> trans-permethrin. An interesting situation here is that the relative potencies of the six compounds correspond well with their acute toxicity estimated using the LD50.


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9366040&dopt=Abstract

Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 1997 Sep;118(1):97-103

Neurotoxic action of six pyrethroid insecticides on the isolated sciatic nerve of a frog (Rana ridibunda).

Theophilidis G, Benaki M, Papadopoulou-Mourkidou E.

Department of Zoology, School of Biology, Aristotle University, Thessaloniki, Macedonia, Greece. theophil@bio.auth.gr

The neurotoxic action of six pyrethroid insecticides, four type II, (flucythrinate, deltamethrin, fenvalerate, fluvalinate) and two type I (cis- and trans-permethrin) was compared on the isolated sciatic nerve of frog. The nerve was exposed to pyrethroids for 30 min and action potentials were recorded for more than 45 hr after exposure. From the plots of the amplitude of the compound action potential vs time, it was possible to estimate, for each compound, the minimum effective concentration, the concentration which is required to reduce the amplitude of the compound action potential to 50% of its control value (mEC50). Flucythrinate was the most toxic compound, while toxicity decreased in the value: deltamethrin > fenvalerate > fluvalinate >> cis-permethrin > trans-permethrin. Low neurotoxicity of cis-permethrin and trans-permethrin (type I pyrethroids) was expected. The neurotoxicity of type I pyrethroids is mainly due to an action at the synapse, which are not present in the frog sciatic nerve preparation. The relative potencies of the four type II compounds agree with their acute toxicity estimated using the LD50.

PMID: 9366040 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=8030177&dopt=Abstract

Vet Parasitol 1994 Mar;52(1-2):113-28

Controlled release insecticide devices for protection of sheep against head strike caused by Lucilia cuprina.

James PJ, Mitchell HK, Cockrum KS, Ancell PM.

Department of Primary Industries, Adelaide, Australia.

The effectiveness of polymer matrix tags containing (w/w) 8.5% cypermethrin, 7.5% flucythrinate, 13.7% tetrachlorvinphos or 20.0% diazinon in protecting sheep against head strike by the sheep blowfly (Lucilia cuprina Wiedemann) was investigated in larval implant, fly cage and field studies. Tags impregnated with cypermethrin reduced the total number of egg masses deposited on the heads of sheep in fly cage studies over a 6 week period by 73.3% compared with no treatment. Tags impregnated with flucythrinate reduced the number of egg masses by 25.3% over 21 weeks but there were no significant differences (P < 0.05) between treated and untreated sheep at individual exposures. Egg masses were found on the majority of tagged sheep and no protection was provided against implants with first instar L. cuprina larvae by either cypermethrin or flucythrinate tags. Tags impregnated with diazinon gave longer protection than treatment with a liquid formulation containing 400 ppm diazinon in larval implant, fly cage and field studies. Over a 12 week period in field studies, 6.6% of rams treated with diazinon tags became struck compared with 30% treated by diazinon jetting, 35.7% treated with plastic tags not impregnated with insecticide and 24.2% of untreated rams. When the rams were exposed to high populations of L. cuprina in an exposure house from 13 to 18 weeks after treatment, 3.3% of rams treated with diazinon tags, 57.1% treated by diazinon jetting, 43.8% treated with plastic tags and 23.5% of untreated rams became struck. Most strikes in the diazinon tagged sheep occurred at sites which were not contacted by the tags. Tags impregnated with tetrachlorvinphos reduced the number of strikes in comparison with no treatment in larval implant and fly cage studies but the results were inconsistent and not as good as those from diazinon tags. It is concluded that well designed controlled release devices that reliably contact the wool on the heads of sheep at sites of flystrike risk and which are able to withstand damage from rams fighting may be able to give prolonged protection against head strike.

Publication Types:

  • Clinical Trial
  • Randomized Controlled Trial

PMID: 8030177 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1875360&dopt=Abstract

J Med Entomol 1991 May;28(3):322-9

Stimulation of vitellogenesis by pyrethroids in mated and virgin female adults, male adults, and fourth instar females of Ornithodoros moubata (Acari: Argasidae).

Taylor D, Chinzei Y, Ito K, Higuchi N, Ando K.

Department of Medical Zoology, School of Medicine, Mie University, Tsu, Japan.

The effects of several pyrethroids on vitellogenesis, i.e., vitellogenin (Vg) synthesis and ovarian development in unfed mated female adults of Ornithodoros moubata were investigated. Survival of ticks treated with pyrethrin, resmethrin, and etophenprox was very low. Ticks treated with cypermethrin (CyM), fenvalerate (Fev), and flucythrinate (Flu) survived even when high concentrations were used. Vg titer in the hemolymph of unfed mated females was the same level on day 5 and about three times higher on day 10 after treatment with CyM, Fev, and Flu, as that of engorged adult females. CyM was the most effective in inducing vitellogenesis and was further evaluated in unfed virgin females, males, and fourth instars. CyM was shown to stimulate vitellogenesis in unfed virgin females adults. Oviposition did not occur but ovaries were well developed. CyM also was shown to stimulate Vg in the hemolymph of unfed and fed adult males; however, the Vg levels were very low compared to that of engorged adult females. Extremely high concentrations of Vg were observed in the hemolymph of female nymphs (fourth instar), particularly engorged nymphs, treated with CyM (10 micrograms). No ovarian development was observed in these nymphs. Vg stimulated by CyM was shown to be immunologically and electrophoretically the same as that of normal engorged females.

PMID: 1875360 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3693665&dopt=Abstract

J Econ Entomol 1987 Oct;80(5):1035-8

Effect of cattle breed and flucythrinate-impregnated ear tags on horn fly (Diptera: Muscidae) control on yearling heifers.

Brethour JR, Harvey TL, Negus R, Corah L, Patterson D.

PMID: 3693665 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3576578&dopt=Abstract

Tijdschr Diergeneeskd 1987 Apr 1;112(7):396-400

[Effectiveness of a PVC ear tag impregnated with the insecticide flucythrinate]

[Article in Dutch]

Sol J, Prijs HJ, Counotte GH, Kommerij R.

A PVC ear tag containing the synthetic pyrethroid flucythrinate was tested in seventeen herds including 218 heifers. There was a comparable control group of twelve herds including 157 heifers. The ear tags were more effective against sucking flies than they were against sticking flies. Varying with the species of the fly, the effectiveness ranged from 36.2 per cent to 95.7 per cent. The effectiveness also varied between the herds. The active constituent was still released within approximately 5 1/2 months after introduction.


PMID: 3576578 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3950188&dopt=Abstract

J Econ Entomol 1986 Feb;79(1):152-7

Evaluation of flucythrinate- and fenvalerate-impregnated ear tags and permethrin ear tapes for fly (Diptera: Muscidae) control on beef and dairy cattle in northwest Florida.

Hogsette JA, Ruff JP.

PMID: 3950188 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4063221&dopt=Abstract

Br J Ind Med 1985 Nov;42(11):773-6

Variation in cutaneous perfusion due to synthetic pyrethroid exposure.

Flannigan SA, Tucker SB.

Synthetic pyrethroids are neurotoxic insecticides with a low mammalian toxicity. Prior investigations have found these agents to be neither cutaneous irritants nor sensitisers. Clinically demonstrable inflammation, as judged by erythema, oedema, or vesiculation, has not been apparent. Nevertheless, paraesthesia does result from cutaneous exposure. In this investigation technical grade flucythrinate was applied to the forearms of human participants twice daily for five consecutive days. Laser Doppler velocimeter measurements were made before each topical application, with histamine phosphate being intradermally injected on termination of the study. Results of both laser Doppler velocimetry and histamine induced axon reflex vasodilatation were not statistically significant at an alpha = 0.05 level. This investigation suggests that the synthetic pyrethroids have little influence on neurogenic vasodilatation on topical exposure.

PMID: 4063221 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4082447&dopt=Abstract

Vet Parasitol 1985 Oct;18(3):229-34

Cattle fly control using controlled-release insecticides.

Tarry DW.

Field trials were carried out from 1980 to 1984 on the use of a controlled-release pesticidal fly control technique on farms in Sussex, England, with a recurrent infectious keratoconjunctivitis problem related to fly attack. Pesticide impregnated p.v.c. ear-tags provided control of biting and disease-carrying fly species throughout the season. Over 90% control of flies, compared with untreated herds, was attained using 2 tags impregnated with cypermethrin, fenvalerate or flucythrinate, although control using a single tag was unsatisfactory. In all cases infectious keratoconjunctivitis was almost completely eliminated.


PMID: 4082447 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4024420&dopt=Abstract

Vet Rec 1985 May 25;116(21):566-7

Effect of flucythrinate impregnated ear tags on fly attack in cattle.

Taylor SM, Mallon T, Elliott CT, Blanchflower J.

PMID: 4024420 [PubMed - indexed for MEDLINE]


http://www.epa.gov/ged/publica/c0280.htm

J Agric Food Chem 1983 Jan-Feb;31(1):104-13

EPA-600/J-82-030.

Acute toxicity, bioconcentration, and persistence of AC 222,705, benthiocarb, chlorpyrifos, fenvalerate, methyl parathion, and permethrin in the estuarine environment.

Schimmel SC, Garnas RL, Patrick JM Jr, Moore JC.

Six pesticides were evaluated in laboratory studies to determine acute (96-h) toxicity, octanol-water partition coefficients (log P), solubility, and persistence in seawater. In addition, three of the six pesticides (synthetic pyrethroids) were tested using the eastern oyster (Crassostrea virginica) in long-term (28-day) tests to determine their respective bioconcentration factors (BCF). Acute toxicity tests provided the following decreasing order of toxicity to estuarine crustaceans and fishes: AC 222,705, fenvalerate, permethrin, chlorpyrifos, methyl parathion, and benthiocarb. The estuarine mysid (Mysidopsis bahia) was consistently the most sensitive species, with LC50 values as low as 0.008 µg/L. The sheepshead minnow (Cyprinodon variegatus) was generally the least sensitive (range of LC50 values = 1.1-1370 µg/L). log P values were inversely related to solubility in seawater. The following are the increasing order of log P values (range, 1.8-6.5) and decreasing order of solubility (range >1000-24 µg/L): methyl parathion, benthiocarb, chlorpyrifos, AC 222,705, fenvalerate, and permethrin. Pesticide half-lives in sediment-water studies ranged from 1.2 to 34 days and were in the following order of increasing persistence: methyl parathion, permethrin, benthiocarb, AC 222,705, chlorpyrifos, and fenvalerate. The steady-state BCF's of the three synthetic pyrethroids were 1900 for permethrin, 2300 for AC 222,705 and 4700 for fenvalerate. After termination of the exposure, each insecticide was depurated by oysters to nondetectable concentrations within one week.

PMID: 6681821 [PubMed - indexed for MEDLINE]

Note from EC: Flucythrinate was also known as AC 222,705


AQUAT TOXICOL 3:171-182,1983

TOXICITY OF THE SYNTHETIC PYRETHROIDS, PERMETHRIN AND AC 222, 705 AND THEIR ACCUMULATION IN EARLY LIFE STAGES OF FATHEAD MINNOWS AND SNAILS

SPEHAR RL, TANNER DK, NORDLING BR

Taxonomic Name: PIMEPHALES PROMELAS

Test Object: FISH, FATHEAD MINNOW

Experimental Conditions: WATERBORNE

Name of Agent (CAS RN):
PERMETHRIN ( 52645-53-1 )
AC 222,705 ( 70124-77-5 )

Assay Method:
VIABILITY, FERTILITY AND MORTALITY
GROWTH
BEHAVIOR AND PSYCHOLOGIC PROCESSES
MUSCULOSKELETAL SYSTEM
NERVOUS SYSTEM

Stage Treated: EMBRYO FRY


US EPA Research Product.

1983. EPA-600/J-83-106. Environ. Toxicol. Chem. 2(2):251-258. (ERL,GB 462)

(Avail. from NTIS, Springfield, VA: PB84-117415) .

Effects of the Synthetic Pyrethroids AC 222, 705, Permethrin, and Fenvalerate on Sheepshead Minnows in Early Life-Stage Toxicity Tests.

Hansen, David J., Larry R. Goodman, James C. Moore and Peggy K. Higdon.

Sheepshead minnows (Cyprinodon variegatus) were exposed to the synthetic pyrethroid insecticides AC 222,705, fenvalerate and permethrin for 28 days in early life stage toxicity tests. AC 222,705 was 370 times more toxic than permethrin and 30 times more toxic than fenvalerate with survival and size of newly hatched fish being the most sensitive measures of effect. AC 222,705 reduced survival of hatched fish 0.61 µg/L and their average weight at 0.06 µg/L; no effects were detected at 0.03 µg/L. Two of the AC 222,705 concentrations that diminished weights, 0.06 and 0.12 µg/L, were below our limit of chemical detection, 0.15 µg/L. Permethrin reduced survival of hatched fish at 22 µg/L; no effects were detected at 10 µg/L. Fenvalerate reduced survival of hatched fish are 3.9 µg/L and both weight and length at 2.2 µg/L; no effects were detected at 0.56 µg/L. Permethrin reduced survival of hatched fish at 22 µg/L and no effects were detected at 10 µg/L. The quotient of the 96-hr LC50 divided by the no-effect concentration was 0.8 for permethrin, 9 for fenvalerate and 37 for AC 222,705. The mean bioconcentration factors, concentrations measured in whole fish divided by concentrations measured in exposure water, were 480 for permethrin and 570 for fenvalerate; AC 222,705 was not detected in fish that survived the exposure.

Note from EC: Flucythrinate was also known as AC 222,705


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7437564&dopt=Abstract

Bull Environ Contam Toxicol 1980 Oct;25(4):608-15

Dislodgable insecticide residues on cotton foliage: acephate, AC 222,705, EPN, fenvalerate, methomyl, methyl parathion, permethrin, and thiodicarb.

Ware GW, Estesen BJ, Buck NA.

PMID: 7437564 [PubMed - indexed for MEDLINE]

Note from EC: Flucythrinate was also known as AC 222,705


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