Insecticides permethrin

Nakamura Y, Sugihara K, Sone T, Isobe M, Ohta S, Kitamura S (2007) The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology 235 176-184... 

Maloney SE, Maule A, Smith ARW (1988) Microbial transformation of the pyrethroid insecticides permethrin, deltamethrin, fastac, fenvalerate, and fluvalinate. Appl Environ Microbiol 54 2874—2876... 

House WA, Long JLA, Rae JE, Parker A, Orr DR (2000) Occurrence and mobility of the insecticide permethrin in rivers in the southern Humber catchment, UK. Pest Manag Sci 56 597-606... 

The biologically patterned insecticide Permethrin, developed by M. Elliott s team at Rothamstead, contains ester (3). Disconnection a) gives a starting material with a tertiary halide (4), yet even this cyclises readily in base, ring formation being so favourable. 

Figure 1. Examples of Phase I and Phase II metabolites of the carbamate insecticide carbanolate, the synthetic pyrethroid insecticide permethrin, and the wood preservative pentachlorophenol...

With the above discussion in mind, it may be assumed that chiral xenobi-otics are likely to be present in various foodstuffs, as human food comprises the meat of fish, birds and terrestrial animals, and of course vegetables. Many chiral pesticides are used to control insects in vegetables and cereals, and hence the presence of these pesticides in the food products is to be expected. Only a few reports are available dealing the presence of chiral pesticides in various foodstuffs. The cholinesterase inhibition activity of chiral organophosphorous pesticides, as well as that of toxic organophosphorous pesticides nerve gases, are enantioselective in nature. Scientists at the Microbiological and Chemical Exposure Assessment Research Division of NERL in Cincinnati, USA, have found the chiral insecticide permethrin, a pyrethroid insecticide, in spinach. Similarly, malathion has been observed in blackberry extract [146]. 

Elliott M, Famham AW, Janes NF, Needhan DH, Pulman DA (1974) Synthetic insecticides with a new order of activity. Nature (London) 248 710-711 Elliott M, Janes NF, Pulman DA, Gaughan LC, LFnai T, Casida JE (1976) Radiosynthesis and metabolism in rats of the IR-isomers of the insecticide permethrin. J Agric Food Chem 24 270-276... 

The horn fly Haematobia irritans an important bloodsucking pest of catde, was found to be completely controlled by ear tags which slowly released permethrin and fenvalerate. These were found to give almost 100% control for 24 weeks. However, following almost universal appHcation of this ideal control measure, control failures of the pyrethroid insecticides were widely reported in North America in 1982 ndash 1983 and the practice is now abandoned. 

Encapsulated fonofos, a soil insecticide, was developed to coat seeds before they were planted (72). Encapsulation reduces oral toxicity 100-fold and dermal toxicity 10-fold while extending activity of the fonofos. Other encapsulated pesticides available include permethrin and parathion (69). Significantly, all commercial encapsulated pesticides are prepared by interfacial polymeri2ation. 

The structures of some pyrethroid insecticides are shown in Figure 12.1. They are all lipophilic esters showing some structural resemblance to the natural pyrethrins. They can all exist in a number of different enantiomeric forms. Permethrin, cypermethrin, and deltamethrin, for example, all have three asymmetric carbon atoms... 

Kim, I.Y., Han, S.Y., and Kang, T.S. et al. (2005). Pyrethroid insecticides, fenvalerate and permethrin, inhibit progesterone-induced alkaline phosphatase activity in T47D human breast cancer cells. Journal of Toxicology and Environmental Health—Part A—Current Issues 68, 2175-2186. 

Mixtures of stereoisomeric 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acids (the acid moieties of permethrin insecticide), CDI, and chiral amines have been investigated by capillary gas chromatography. The diastereomeric amides could be identified by GC/MS-spectrometry [413... 

Buck, N.A., B.J. Estesen, and G.W. Ware. 1980. Dislodgable insecticide residues on cotton foliage fenvalerate, permethrin, sulprofos, chlorpyrifos, methyl parathion, EPN, oxamyl, and profenofos. Bull. Environ. Contam. Toxicol. 24 283-288. 

Gambrell et al. [14] have described a procedure for the recovery of DDT (also kepone and Permethrin) added to soil suspensions incubated under controlled redox potential and pH conditions. They studied the effect of time on the levels of the insecticides and their breakdown products. 

DDT, Kepone and Permethrin were added to soil and incubated under controlled pH and redox potential conditions to determine the effect with time on the levels of the insecticides and their degradation products. Samples were analysed using gas chromatography, pH and redox potential affected the persistence of pesticides to different degrees. The recovery of DDT was affected by redox potential but not by pH. The stability of Kepone was not affected by pH or redox potential but Permethrin stability was affected by both. 

Tilson HA, Hong JS, Mactutus CF. 1985. Effects of 5,5-diphenylhydantoin (phenytoin) on neurobehavioral toxicity of organochlorine insecticides and permethrin. J Pharmacol Exp Ther... 

Selenium sulphide, coal tar, ketoconazole and salicylic acid are agents that can be used in dandruff. Permethrin is an insecticide indicated in the eradication of head lice. Permethrin is available as alcoholic or aqueous lotions. 

Bioallethrin is a synthetic pyrethrin insecticide. Piperonylbutoxide, a weak insecticide itself, has synergistic activity. The same holds true for the combination of pyrethrum extract with piperonylbutoxide. These combinations have the same efficacy as permethrin. Local irritation occurs frequently effect and contact with mucous membranes and the eyes must be avoided. 

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