Abstracts
Fenfluthrin
CAS No. 75867-00-4

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ACTIVITY: Insecticide (pyrethroid)

CAS Name: (1R-trans)-(pentafluorophenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Structure:


Reports available from
The National Technical Information Service
(NTIS)

Order from NTIS by: phone at 1-800-553-NTIS (U.S. customers); (703)605-6000 (other countries); fax at (703)605-6900; and email at orders@ntis.gov. NTIS is located at 5285 Port Royal Road, Springfield, VA, 22161, USA.

Order No. Title Keywords

NTIS/OTS0538106

EPA/OTS; Doc #88-920007049

1992 - INIT SUB: NEUROTOXICITY STUDIES WITH NAK 1654 IN HENS WITH COVER LETTER DATED 09-10-92

BAYER AG

MILES INC
NAK 1654
HEALTH EFFECTS
NEUROTOXICITY
BIRDS
ORAL
GAVAGE
CAS Registry Numbers: 75867-00-4

NTIS/OTS0555590

EPA/OTS; Doc #88-920010108

1992 - INITIAL SUBMISSION: ACUTE AND SUBACUTE TOXICITY STUDIES OF NAK 1654 WITH COVER LETTER DATED 08/17/92
Corporate Name: INSTITUT FUR TOXIKOLOGIE
MILES INC
NAK 1654
HEALTH EFFECTS
ACUTE TOXICITY
MAMMALS
RATS
ORAL
DIET
MICE
DOGS
PARENTERAL
INTRAPERITONEAL
SUBCUTANEOUS
DERMAL
INHALATION
SUBCHRONIC TOXICITY
PRIMARY DERMAL IRRITATION
RABBITS
PRIMARY EYE IRRITATION
NEUROTOXICITY
BIOCHEMISTRY
TISSUE CONCENTRATION
CAS Registry Numbers: 75867-00-4

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.

Abstract: 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.

 

http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10810595&dopt=Abstract

J Commun Dis 1999 Jun;31(2):91-9

Evaluation of cyfluthrin and fenfluthrin for their insecticidal activity against three vector mosquitoes.

Mohapatra R, Ranjit MR, Dash AP.


Regional Medical Research Centre, Bhubaneswar, Orissa, India.

The EC50/EC90 concentrations of cyfluthrin and fenfluthrin were tested for their activity against different developmental stages of three important vector mosquitoes viz., Anopheles stephensi Liston, Aedes aegypti (Linn.) and Culex quinquefasciatus Say. The EC90 concentrations of both cyfluthrin and fenfluthrin showed ovicidal effect on An. Stephensi and Ae. aegypti whereas EC90 of cyfluthrin checked the hatching of eggs completely in Cx. quinquefasciatus. Fenfluthrin at EC50 concentration reduced the percentage of hatching significantly (p < 0.05) only in An. stephensi. Both the compounds were more active against the fourth larval instars of all mosquito species and cyfluthrin in culicines (17.3% Ae. aegypti = 9.1%) and fenfluthrin in anophenlines (An. stephensi = 36.8%) brought about maximum inhibition in adult emergence. Various types/degrees of morphogenetic aberrations were induced in all mosquito species on treatment with these compounds. Cyfluthrin treated female mosquitoes showed reduced fecundity rates in An. stephensi (p < 0.05), Cx. quinquefasciatus (p < 0.001) and fenfluthrin treated in An. stephensi (p < 0.5) and Ae. aegypti (p < 0.05). The fertility rates of all the mosquito species were significantly reduced (p < 0.001) by both the compounds.

PMID: 10810595 [PubMed - indexed for MEDLINE]


From Toxline at TOXNET

PESTIC BIOCHEM PHYSIOL; 39 (3). 1991. 210-218

Phenylpyrazoles, a new class of pesticides: An electrophysiological investigation into basic effects.

KLIS S FL VIJVERBERG H PM VAN DEN BERCKEN J

Res. Inst. Toxicology, Univ. Utrecht, P.O. Box 80.176, NL-3508 TD Utrecht, Netherlands.

Abstract: BIOSIS COPYRIGHT: BIOL ABS. Phenylpyrazoles constitute a newly developed class of pesticides that may exert direct excitatory effects on the nervous system. Basic electrophysiological effects were investigated in vitro in the sciatic nerve and the lateral-line sense organ of the clawed frog, Xenopus laevis, by recording nerve activity extracellularly. In the slowly adapting stretch receptor organ of the crayfish, Astacus sp., effects on the membrane potential of the neurone were recorded using intracellular microelectrodes. Both in the sciatic nerve and in the lateral-line sense organ the main effect of phenylpyrazoles was to decrease the survival time of the isolated preparation. In the isolated crayfish stretch receptor organ a similar decrease of the survival time was accompanied by a depolarization of the stetch receptor neurone membrane. The depolarizing effect of the phenylpyrazoles is not caused by a modification of the tetrodotoxin-sensitive voltage-dependent Na+ channels, nor by an effect

CAS Registry Number: 75867-00-4


From Toxline at TOXNET

Toxicology and Applied Pharmacology, Vol. 103, No. 3, page 528-538, 43 references,1990

Characteristics of the Prolonged Inhibition Produced by a Range of Pyrethroids in the Rat Hippocampus

Joy RM, Lister T, Ray DE, Seville MP

1990 Abstract: The effects of eight different synthetic pyrethroids were determined on the excitability of hippocampal granule cells in urethane anesthetized rats. Electrodes were stereotactically placed in the brain of male LAC-Porton-rats. Square wave pulses 0.1 millisecond in duration were used as stimuli. The pyrethroids tested were fenfluthrin (75867004), cismethrin (35764591), NRDC-108 (18877899), cyphenothrin (39515407), fenproponate, RU-26941 (67670671), fenvalerate (51630581), and deltamethrin (52918635). The depression of granule cell excitability that follows stimulation of the major synaptic input, the perforant path, was prolonged by all eight compounds. The class to which the pyrethroid belonged determined the magnitude of this effect. The depression of granule cell excitability was prolonged by type-I pyrethroids for shorter periods than type-II pyrethroids or pyrethroids producing a mixed type of intoxication. Cismethrin, a type-I pyrethroid, was tested over a dose range of 1.5 to 24 times the conscious rat intravenous median lethal dose to determine whether the difference observed between type-I and type-II pyrethroids was the result of the selection of doses. The prolongation even at the highest dose remained well below that produced by type-II pyrethroids. Deltamethrin caused an effect which was consistent with the production or potentiation of a surmountable inhibitory response. This action of deltamethrin was antagonizable by mephenesin and lidocaine, but not by picrotoxin or halothane. This type of effect, its time course, and the antagonism data suggest that type-II pyrethroids enhance inhibition in the dentate gyrus. This action does not appear to be mediated by GABA-A receptors.

Defintions:

Dentate gyrus - one of the two interlocking gyri composing the hippocampus, the other one being the Ammon horn.

Gyrus. gen and pl. gyri - one ot the prominent rounded elevations from the cerebral hemispheres, each consisting of an exposed superficial portion and a portionhidden from view in the wall and floor of the sulcus.

Sulcus - 1. one of the g rooves or furrows on the surface of the brain, bounding the several convolutions or gyri; a fissure. 2. any long narrow groove, furrow, or slight depression. 3. a groove or depression in the oral cavity or on the surface of a tooth.

Ref: Stedman's Concise Medical Dictionary for the Health Proessions. Illustrated 4th Edition. Ed. JH Dirckx. Lippincott Williams & Wilkins. A Wolters Kluwer Company.

CAS Registry Numbers: 51630-58-1 - Fenvalerate
75867-00-4 - Fenfluthrin 39515-40-7 - Cyphenothrin
67670-67-1 - Fenproponate, RU-26941 35764-59-1 - Cismethrin
52918-63-5 - Deltamethrin 18877-89-9 - NRDC-108

From Toxline at TOXNET

PESTIC BIOCHEM PHYSIOL; 34 (2). 1989. 164-173.

EFFECTS OF PYRETHROIDS ON NEUROTRANSMITTER-OPERATED ION CHANNELS IN CULTURED MOUSE NEUROBLASTOMA CELLS

OORTGIESEN M VAN KLEEF R G DM VIJVERBERG H PM

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM ALLETHRIN IR-CIS CYPHENOTHRIN IR-CIS FENFLUTHRIN INSECTICIDE


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3238775&dopt=Abstract

Trop Anim Health Prod 1988 Nov;20(4):267-8

No Abstract available

Pyrethroid impregnated ear tags in trypanosomiasis control.

Dolan RB, Sayer PD, Alushula H, Heath BR.

Kenya Trypanosomiasis Research Institute, Kikuyu.

PMID: 3238775 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3376131&dopt=Abstract

Toxicology 1988 May;49(2-3):271-6

Effects of pyrethroids on the acoustic startle reflex in the rat.

Hijzen TH, De Beun R, Slangen JL.

Department of Psychophysiology, State University of Utrecht, The Netherlands.

The effects of NAK 1901 (Pentafluorbenzyl (1R, cis)-3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-carboxylate) and cypermethrin ((S,R)-alpha-cyano-3-phenoxybenzyl-2,2-dimethyl (1R, 1S, cis, trans)-3-(2,2-dichlorovinyl) cyclopropane-carboxylate) (RU 24 501) on amplitude and prepulse inhibition of the acoustic startle reflex were studied in male Wistar rats. NAK 1901 (0, 1, 2.5, 4 mg/kg p.o.) enhanced the amplitude of the startle reflex in a dose-dependent way. Startle latency was not affected. Cypermethrin (0, 0.5, 1, 2 mg/kg p.o.) had no effect on the amplitude or the latency of the startle reflex. Both NAK 1901 and cypermethrin administration produced a dose-dependent increase in toxic signs and a dose-dependent increase in weight loss during the experimental session. None of the pyrethroids affected prepulse inhibition of the startle reflex. Because the neural substrate of the inhibitory processes involved in prepulse inhibition are probably of supraspinal origin, it is suggested that these substrates are not affected by pyrethroids.

PMID: 3376131 [PubMed - indexed for MEDLINE]


From Toxline at TOXNET

Toxicology Letters, Vol. 40, No. 2, pages 141-152, 18 references, 1988

Effects of Type I and Type II Pyrethroids on the Startle Response in Rats

Hijzen TH, Slangen JL

Abstract: The effects of type-I and type-II pyrethroids on the startle response of male Wistar-rats were studied in three experiments. Type-I and type-II compounds were distinguished by the absence or presence of a cyanophenoxybenzyl moiety. In experiment one, male rats were fed 30, 60 or 90mg/kg cis-permethrin (61949766) (type-I) or 60, 90 or 120mg/kg cis,trans-cypermethrin (type-II), and were startled before and after treatment by pulses of a pure tone of 9 kilohertz (kHz) with an intensity of 120 decibels (dB). Three weeks later the animals were given the same doses and subjected to pulses of a tone of 4kHz, 70dB. Startle amplitude, measured as displacement of the floor of a hanging cage, increased as a function of dose, with similar results for both the first and second sets of treatments. Overt behavior and habituation of the startle response were not affected. In experiment two, rats received 0, 2, 4 and 6mg/ml deltamethrin (52918635) (type-II) or 0, 1, 2.5 and 4mg/kg fenfluthrin (75867004) (NAK-1901, type-I). Each rat was exposed to each of the doses and to tone and light shock stimuli. Deltamethrin had no effect on startle, while fenfluthrin resulted in a dose dependent increase in the startle amplitude, and neither compound affected potentiation of the startle reflex. In experiment three, each rat received each of doses of 0, 2, 4 and 6mg/kg deltamethrin and the startle intensity was 120dB. Two hundred startle stimuli were presented at each session, and blocks of the first, middle and last 30 trials were analyzed. The startle amplitude decreased significantly in successive trial blocks, demonstrating the effect of habituation. The authors conclude that the effects of type-II pyrethroids on startle amplitude are mediated by an indirect metabolic effect and a direct effect at the site of the muscle, and also that supraspinal mechanisms are not influenced by the doses of pyrethroids administered.


From Toxline at TOXNET

PESTIC BIOCHEM PHYSIOL; 30 (1). 1988. 79-86.

CLASSIFICATION OF THE ACTIONS OF TEN PYRETHROID INSECTICIDES IN THE RAT USING THE TRIGEMINAL REFLEX AND SKELETAL MUSCLE AS TEST SYSTEMS

WRIGHT C DP FORSHAW PJ RAY DE

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM SENSORY GANGLION MOTOR NUCLEUS DIAPHRAGM MUSCLE MEMBRANE ELECTROPHYSIOLOGY

CAS Registry Numbers 68085-85-8
Cyhalothrin
64312-66-9
Cyclopropanecarboxylic acid, 3-(2,2-dimethylethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1R-(1-alpha(S*),3-alpha))-
35764-59-1
Cismethrin
75867-00-4
Fenfluthrin
67890-40-8
Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-,cyano(3-phenoxyphenyl)methyl ester, (R*,R*)-
64257-84-7
Fenpropathrin
18877-89-9
NRDC-108
68359-37-5
Cyfluthrin
67670-66-0
Fluorocyphenothrin
52918-63-5
Deltamethrin

http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2449265&dopt=Abstract

Brain Res 1987 Dec 29;437(2):309-22

Increase of sodium current after pyrethroid insecticides in mouse neuroblastoma cells.

Ruigt GS, Neyt HC, Van der Zalm JM, Van den Bercken J.

Department of Veterinary Pharmacology, Pharmacy and Toxicology, University of Utrecht, The Netherlands.

The effects of 4 different pyrethroid insecticides on sodium channel gating in internally perfused, cultured mouse neuroblastoma cells (N1E-115) were studied using the suction pipette, voltage clamp technique. Pyrethroids increased the amplitude of the sodium current, sometimes by more than 200%. Activation of the sodium current occurred at more hyperpolarized potentials than under control conditions. The declining phase of the sodium current during depolarization was markedly slowed down and after repolarization of the membrane a large, slowly decaying sodium tail current developed. Pyrethroids did not affect the sodium current reversal potential, steady-state sodium inactivation or recovery from sodium channel inactivation. The amplitude of the pyrethroid-induced slow tail current was always proportional to the sodium current at the end of the preceding depolarizing pulse. The rate of decay of the slow tail current strongly depended on pyrethroid structure and increased in the order deltamethrin, cyphenothrin, fenfluthrin and phenothrin. The rate of decay further depended on membrane potential and temperature. Below -85 m V the instantaneous current-voltage relationship of the slow tail current showed a negative slope conductance. The tail current decayed more slowly at low temperatures. Arrhenius plots indicated that the relaxation of open sodium channels to a closed state involved a higher energy barrier for pyrethroid-affected than for normal channels. The energy barrier was higher after deltamethrin than after the non-cyano pyrethroid fenfluthrin. It is concluded that in mammalian neuronal membrane pyrethroids selectively reduce the rate of closing of sodium channels both during depolarization and after repolarization of the nerve membrane.

PMID: 2449265 [PubMed - indexed for MEDLINE]


From Toxline at TOXNET

J COMP PHYSIOL A SENS NEURAL BEHAV PHYSIOL; 159 (1). 1986. 43-54.

PRONOUNCED REPETITIVE ACTIVITY INDUCED BY THE PYRETHROID INSECTICIDE FENFLUTHRIN IN THE SLOWLY ADAPTING STRETCH RECEPTOR NEURON OF THE CRAYFISH

RUIGT G SF KLIS J FL VAN DEN BERCKEN

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM DDT TETRODOTOXIN FENFLUTHRIN REPRESSOR SODIUM-POTASSIUM PUMP SPIKE TRIGGER ZONE ELECTROPHYSIOLOGY ACTION POTENTIAL AXON SOMA NEUROTOXIN


From Toxline at TOXNET

FORD, M. G., ET AL. (ED.). ELLIS HORWOOD SERIES IN BIOMEDICINE: NEUROPHARMACOLOGY AND PESTICIDE ACTION; NEUROTOX '85, BATH, ENGLAND, 1985. 512P. VCH PUBLISHERS, INC.: NEW YORK, NEW YORK, USA; WEINHEIM, WEST GERMANY; ELLIS HORWOOD LTD.: CHICHESTER, ENGLAND (DIST. IN THE USA AND CANADA BY VCH PUBLISHERS: DEERFIELD BEACH, FLORIDA, USA) ILLUS. ISBN 0-89573-424-9; ISBN 3-527-26340-3.; 0 (0). 1986. 267-286.

THE EFFECT OF PYRETHROID STRUCTURE ON THE INTERACTION WITH THE SODIUM CHANNEL IN THE NERVE MEMBRANE

VIJVERBERG H PM DE WEILLE JR RUIGT G SF VAN DEN BERCKEN J

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM FROG MOUSE NEUROBLASTOMA CELL INSECTICIDE STRUCTURE-ACTIVITY RELATIONSHIP MODE OF ACTION

CAS Registry Numbers: 57731-67-6
Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, ethynyl(3-phenoxyphenyl)methyl ester
52315-07-8 39515-40-7
Cyphenothrin
10453-86-8
Resmethrin
102407-97-6
(no info found)
52918-63-5
Deltamethrin
51630-58-1
Fenvalerate
35764-59-1
Cismethrin
584-79-2
Bioallethrin
75867-00-4
Fenfluthrin 
52645-53-1
Permethrin
39515-41-8 26002-80-2
Phenothrin
-

From Toxline at TOXNET

INTERNATIONAL SYMPOSIUM ON NEUROPHARMACOLOGY AND PESTICIDE ACTION HELD AT NEUROTOX '85, BATH, ENGLAND, MAR. 31-APR. 4, 1985.

PESTIC SCI; 16 (5). 1985. 545-546.

INVESTIGATION OF THE RELATIONSHIP BETWEEN THE NEUROPHYSIOLOGICAL EFFECTS OF TWO STRUCTURALLY RELATED PYRETHROIDS AND THEIR IN-VIVO TOXICITY

BUCKLEY DS, LEAKE LD, FORD MG

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM ABSTRACT MUSCA-DOMESTICA HIRUDO-MEDICINALIS STRUCTURE-ACTIVITY RELATIONSHIP KNOCKDOWN INSECTICIDE MODE OF ACTION

CAS Registry Numbers: 75867-00-4
Fenfluthrin 
52918-63-5
Deltamethrin
28434-00-6
S-Bioallethrin

From Toxline at TOXNET

190TH AMERICAN CHEMICAL SOCIETY NATIONAL MEETING, CHICAGO, ILL., USA, SEPT. 8-13, 1985. ABSTR PAP AM CHEM SOC; 190 (0). 1985. NO PAGINATION.

SYNTHESIS AND ARTHROPODICIDAL PROPERTIES OF HIGHLY POTENT FLUORINATED PYRETHROIDS

ARLT D, BEHRENZ D, FOERSTER H, FUCHS R, HAMANN I, HARTMANN W, HEINE HG, HOFFMANN H, JAUTELAT M, ET AL

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM ABSTRACT LEVO-1R-TRANS FENFLUTHRIN CYFLUTHRIN FLUMETHRINE HYGIENE AGRICULTURE VETERINARY USE


From Toxline at TOXNET

KIEL MILCHWIRTSCH FORSCHUNGSBER; 37 (2). 1985. 125-212.

STUDIES ON BOVINE SUMMER MASTITIS

TOLLE A, REICHMUTH J, FRANKE V, BEIMGRABEN J

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM MOUSE HAEMATOBIA-STIMULANS PEPTOCOCCUS-INDOLICUS CORYNEBACTERIUM-PYOGENES BACTEROIDES HYDROTAEA-IRRITANS HAEMATOBIA-IRRITANS ANTIBIOTIC TREATMENT FENFLUTHRIN INSECTICIDE PYOGENIC MASTITIS VACCINATION GRAZING ENVIRONMENT FLY CONTROL


From Toxline at TOXNET

ANZ SCHAEDLINGSKD PFLANZENSCHUTZ UMWELTSCHUTZ; 58 (2). 1985. 30-35.

CYFLUTHRIN AND FENFLUTHRIN 2 NEW PYRETHROIDS FOR THE CONTROL OF HYGIENE PESTS

BEHRENZ W, ELBERT A

Abstract: BIOSIS COPYRIGHT: BIOL ABS. RRM COCKROACH BEDBUG MOSQUITO FLY PENTAFLUOROPHENYLMETHYL-1R 3R-3-2 2-DICHLOROETHENYL-2 2-DIMETHYLCYCLOPROPANECARBOXYLATE CYANO-4-FLUORO-3-PHENOXYPHENYLMETHYL-3-2 2-DICHLOROETHENYL-2 2-DIMETHYLCYCLOPROPANECARBOXYLATE TOXICITY KNOCK DOWN ACTION


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4054972&dopt=Abstract

Indian J Med Res 1985 Jul;82:1-8

No Abstract available

Evaluation of fenfluthrin (OMS 2013), a synthetic pyrethroid for insecticidal efficacy against mosquito vectors.

Mariappan T, Kalyanasundaram M, Panicker KN, Balakrishnan N, Tyagi BK, Das PK.

PMID: 4054972 [PubMed - indexed for MEDLINE]


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