Metabolism and toxicology of pyrethroids with dihalovinyl substituents.

Replacement of the photolabile and biodegradable isobutenyl substituent of pyrethroids with a dihalovinyl group often leads to improved insecticidal potency and enhanced photostability. This type of structural modification does not greatly alter the ease of detoxification in mammals since other sites in the molecule undergo metabolic attack. The available toxicological information on dihalovinyl pyrethroids indicates that they are suitable replacements for other insecticides with less favorable persistence and toxicological characteristics.

• Publication year

  1977

• Venue

  Environmental Health Perspectives

• Publication date

  1977-12-01

• Fields of study

  Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1289/EHP.7721285PMID 612453PMCID 1475316
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Metabolism of permethrin isomers in American cockroach adults, house fly adults, and cabbage looper larvae

  1978cited by this paper
• New Synthesis of the Acid Moiety of Pyrethroids

  1977cited by this paper
• Photochemical Reactions of Pyrethroid Insecticides

  1977cited by this paper
• Synthesis of isomeric 3-(2,2-dichlorovinyl)-2-hydroxymethyl-2-methylcyclopropanecarboxylic acids and other permethrin metabolites.

  1977cited by this paper
• Synthetic Route to the Acid Portion of Permethrin

  1977cited by this paper
• Metabolism of permethrin in bean plants

  1977cited by this paper
• Substrate Specificity of Mouse-Liver Microsomal Enzymes in Pyrethroid Metabolism

  1977cited by this paper
• Effects of pyrethroid structure on rates of hydrolysis and oxidation by mouse liver microsomal enzymes

  1977cited by this paper
• Pyrethroid photochemistry: decamethrin

  1977cited by this paper
• Stereospecificity of Pyrethroid Metabolism in Mammals

  1977cited by this paper
• Novel Routes to 1,1-Dichloro-4-methyl-1,4-pentadiene and 1,1-Dichloro-4-methyl-1,3-pentadiene

  1977cited by this paper
• Permethrin Metabolism in Rats and Cows and in Bean and Cotton Plants

  1977cited by this paper
• Recent Progress in Syntheses of the New and Most Potent Pyrethroids

  1977cited by this paper
• 3-Phenoxy-α-cyano-benzyl Esters, the Most Potent Synthetic Pyrethroids

  1976cited by this paper
• Mammalian Toxicological Study of Permethrin, 3-phenoxybenzyl(±)-cis, trans-2,2-dimethyl-3-(2, 2-dichlorovinyl)-cyclopropane-1-carboxylate

  1976cited by this paper
• SOLUTION PHOTOCHEMISTRY OF THE POTENT PYRETHROID INSECTICIDE α-CYANO-3-PHENOXYBENZYL CIS-2,2-DIMETHYL-3-(2,2-DIBROMOVINYL)CYCLOPROPANECARBOXYLATE

  1976cited by this paper
• Future use of natural and synthetic pyrethroids

  1976cited by this paper
• Properties and applications of pyrethroids.

  1976cited by this paper
• 2-arylalkanoates, a new group of synthetic pyrethroid esters not containing cyclopropanecarboxylates†

  1976cited by this paper
• Solution photochemistry of the potent pyrethroid insecticide α-cyano-3-phenoxybenzyl cis-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecar☐ylate

  1976cited by this paper
• Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.

  1976cited by this paper
• Permethrin metabolism in rats.

  1976cited by this paper
• Degradation, metabolism and toxicity of synthetic pyrethroids.

  1976cited by this paper
• Mutagenic and carcinogenic effects of vinyl chloride.

  1975cited by this paper
• Structure-biodegradability relationships in pyrethroid insecticides

  1975cited by this paper
• Halopyrethroids. II. A difluoropyrethroid.

  1975cited by this paper
• Insecticidal activity of the pyrethrins and related compounds. VII. Insecticidal dihalovinyl analogues of cis and trans chrysanthemates

  1975cited by this paper
• Synthetic insecticide with a new order of activity

  1974cited by this paper
• The pyrethrins and related compounds. XIX Geometrical and optical isomers of 2,2‐dimethyl‐3‐(2,2‐dichlorovinyl)‐cyclopropanecarboxylic acid and insecticidal esters with 5‐benzyi‐3‐furylmethyi and 3‐phenoxybenzyl alcohols

  1974cited by this paper
• Photodecomposition of resmethrin and related pyrethroids.

  1974cited by this paper
• Insecticidally active conformations of pyrethroids

  1974cited by this paper
• Effect of long-term exposure to 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene, to 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane, and to the two chemicals combined on CF-1 mice.

  1974cited by this paper
• Potent Pyrethroid Insecticides from Modified Cyclopropane Acids

  1973cited by this paper
• New potent pyrethroid, bromethrin.

  1973cited by this paper
• A Photostable Pyrethroid

  1973cited by this paper
• NRDC 143, a more stable pyrethroid

  1973cited by this paper
• Pyrethrum, the natural insecticide.

  1973cited by this paper
• The relationship between the structure and the activity of pyrethroids.

  1971cited by this paper
• Studies on chrysanthemic acid—XXI

  1971cited by this paper
• Oxidative metabolism of pyrethroids in houseflies

  1969cited by this paper
• Photodecomposition of pyrethrin I, allethrin, phthalthrin, and dimethrin. Modifications in the acid moiety

  1969cited by this paper
• O-Demethyl Pyrethrin II Analogs from Oxidation of Pyrethrin I, Allethrin, Dimethrin, and Phthalthrin by a House Fly Enzyme System

  1966cited by this paper
• Chemistry of the natural pyrethrins.

  1961cited by this paper
• Relation between chemical structure and insecticidal activity in pyrethroid compounds. I. An analogue of chrysanthemic acid containing chlorine in the side chain

  1959cited by this paper
• THE AMERICAN CHEMICAL SOCIETY.

  1922cited by this paper

• Advanced multifunctional fabrics enabled by bioinspired coatings

  2024cites this paper
• Distribución y efectos del piretroide ciflutrin sobre el sistema nervioso central

  2018cites this paper
• THE FIELD PRACTICES OF LAMBDACYHALOTHRIN AND DELTAMETHRIN INSECTICIDES AGAINST ADULT MOSQUITOES OF ANOPHELES STEPHENSI AS THE MAIN VECTOR OF MALARIA: RESIDUAL EFFECTS

  2017cites this paper
• How deltamethrin produces oxidative stress in liver and kidney

  2016cites this paper
• Subacute poisoning of mice with deltamethrin produces memory impairment, reduced locomotor activity, liver damage and changes in blood morphology in the mechanism of oxidative stress

  2015cites this paper
• Lethal and Residual Effects of Lambdacyhalothrin, Deltamethrin and Cyfluthrin Insecticides on Adult Mosquitoes of Anopheles stephensi Liston (Diptera: Culicidae) on Different Surfaces

  2014cites this paper
• Parameters for pyrethroid insecticide QSAR and PBPK/PD models for human risk assessment.

  2012cites this paper
• Reviews of Environmental Contamination and Toxicology

  2012cites this paper
• Cytotoxicity induced by deltamethrin and its metabolites in SH-SY5Y cells can be differentially prevented by selected antioxidants.

  2012cites this paper
• Chapter 76 – Pyrethroid Chemistry and Metabolism

  2010cites this paper
• Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development.

  2009cites this paper
• Alternative sample preparation method for photochemical studies based on solid phase microextraction: synthetic pyrethroid photochemistry.

  2007cites this paper
• Characterization of deltamethrin metabolism by rat plasma and liver microsomes.

  2006cites this paper
• In this packet you will find the following : Scientific Studies, Case Histories , Medical Journal Quotes, and Physician ' s Letters that present health concerns associated with exposure to Pyrethrins , Pyrethroids, and added inert ingredients.

  2006cites this paper
• Inhibition of metabolic cooperation in vitro and enhancement of enzyme altered foci incidence in rat liver by the pyrethroid insecticide fenvalerate

  2004cites this paper
• Toxicological profile for pyrethrins and pyrethroids

  2003cites this paper
• Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment.

  2002cites this paper
• CHAPTER 58 – Pyrethroid Chemistry and Metabolism

  2001cites this paper
• Topical Bibliography of Published Works Regarding the Health of Veterans of the Persian Gulf War

  1995cites this paper
• Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus

  1993cites this paper
• Biomarkers of pesticide exposure.

  1992cites this paper
• Neurotoxicology of pyrethrin and the pyrethroid insecticides.

  1991cites this paper
• Toxicology and environmental fate of synthetic pyrethroids.

  1990cites this paper
• Comparative toxicology of the pyrethroid insecticides.

  1989cites this paper
• The pharmacokinetics and metabolism of (1R, cis)- and (1R, trans)-tetramethrin in rats.

  1989cites this paper
• Mutagenic activity in synthetic pyrethroids in Salmonella typhimurium.

  1988cites this paper
• Toxicological studies of deltamethrin.

  1984cites this paper
• Mechanisms of selective action of pyrethroid insecticides.

  1983cites this paper
• Pesticide Metabolism in Plants Reactions and Mechanisms

  1982cites this paper
• An introduction to the metabolism of pyrethroids.

  1980cites this paper
• Metabolic chemistry of pyrethroid insecticides

  1980cites this paper
• Comparative Metabolism of Pyrethroids Derived from 3-Phenoxybenzyl and α-Cyano-3-Phenoxybenzyl Alcohols

  1979cites this paper
• Decamethrin metabolites from oxidative, hydrolytic, and conjugative reactions in mice.

  1979cites this paper
• Metabolism of trans- and cis-permethrin, trans- and cis-cypermethrin, and decamethrin by microsomal enzymes.

  1979cites this paper
• Haloethylene-related compounds of industrial, environmental, and medical significance

  1977cites this paper