Detail of "1166-46-7"

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Neurophysiological activity and toxicity of pyrethroids derived by addition of methylene, sulfur, or oxyen to the chrysanthemate 2-methyl-1-propenyl substituent

Neurophysiological activity and toxicity of pyrethroids derived by addition of methylene, sulfur, or oxyen to the chrysanthemate 2-methyl-1-propenyl substituent. Ruzo, Luis O.; Casida, Joh E.; Gammon, Derek W. (Dep. Entomol. Sci., Univ. California, Berkeley, CA 94720, USA).Some commonly used reagents like 64312-66-9 is used in this experiment. Pestic. Biochem. Physiol., 21(1), 84-91 (English) 1984. CODEN: PCBPBS. ISSN: 0048-3575. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) Conversion of chrysanthemates to their cyclopropane, episulfide, and epoxide derivs. by addn. of methylene, S, or O, resp., to the 2-methyl-1-propenyl double bond yields products generally of reduced toxicity but enhanced neurophysiol. activity and photostability. The reduced toxicity is established with cis-cyphenothrin derivs. administered intracerebrally to mice and topically to house flies and with cis-phenothrin derivs. applied topically to American cockroaches and houseflies, even in the presence of piperonyl butoxide for the houseflies. In contrast, cyclopropane, episulfide, and epoxide derivs. of phenothrin are more potent than the parent compd. in eliciting repetitive firing following stimulation of a cercal sensory nerve of the American cockroach in vitro. The individual 1'R and 1'S isomers of epoxides derived from (1R,cis,aS)cyphenothrin [64312-66-9], (1R,cis)phenothrin, and (1R,trans)tetramethrin [1166-46-7] differ in potency by ~20-fold for insecticidal activity, >30-fold for intracerebral toxicity to mice, and ~100,000-fold in the cercal sensory nerve assay. In each case the epoxide isomer of higher Rf is more potent than that of lower Rf when derived from a trans-chrysanthemate and vice versa from a cis-chrysanthemate. .

Pyrethroid insecticides: actions of deltamethrin and related compounds on insect axonal sodium channels

Pyrethroid insecticides: actions of deltamethrin and related compounds on insect axonal sodium channels. Laufer, J.; Roche, M.; Pelhate, M.; Elliott, M.; Janes, N. F.; Sattelle, D. B. (UER Med., Univ. Angers, Angers 49045, Fr.). J. Insect Physiol., 30(5), 341-9 (English) 1984. CODEN: JIPHAF. ISSN: 0022-1910. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) The actions of deltamethrin [52918-63-5] and 8 other pyrethroids were tested on isolated giant axons of the cockroach Periplaneta americana, using microelectrode and oil-gap, single-fiber electrophysiol. recording techniques. Deltamethrin at micromolar concns. induced a slow progressive depolarization of the axon membrane accompanied by a gradual redn. in the action potential amplitude. The deltamethrin-induced depolarization was enhanced by an increase in stimulation frequency and was reduced in the presence of the Na channel-blocking agent saxitoxin [35523-89-8] (1 ′ 10-7M). Other synthetic pyrethroids (biopermethrin [51877-74-8] and its 1S enantiomer [54774-46-8], biotetramethrin [1166-46-7], s-bioallethrin [28434-00-6], bioresmethrin [28434-01-7] and its 1S enantiomer [91224-53-2], cismethrin [35764-59-1] and kadethrin [58769-20-3]) were also studied. In contrast to the findings with deltamethrin, all other compds., apart from the 1S isomers which were inactive, induced prolonged neg. (depolarizing) after-potentials. Deltamethrin affected a small fraction of Na channels which are held in a modified open-state, whereas the pyrethroids which generate large neg. after-potentials induced a brief alteration of the open-state Na channels with a larger no. of channels affected. Differences between the actions of pyrethroids on insect axonal Na channels and whole insects are discussed.