Water solubility pyrethroid insecticides

Taking the pyrethroids, apart from fenvalerate, they are solids with low water solubility, marked lipophilicity, and low vapor pressure. Fenvalerate is a viscous liquid with an appreciable vapor pressure. Being esters, the pyrethroids are subject to hydrolysis at high pH. They are sufficiently stable to heat and light to be effective insecticides in the field. 

Two synthetic pyrethroid insecticides, bifenthrin and permethrin (3-phenoxybenzyl (lR5)-cis-fra s-3-(2,2-dichlorovinyl)-2,2-dimcthylcyclopropane-carboxylate), are the major runoff constituents considered in our monitoring and evaluation studies. Bifenthrin has a solubility of <1 ppb, and a Koc of240,000 ml g. Permedirin has a solubility of 6 ppb in water, and a Ka- of 100,000 ml g (5). The stroi adsorption on soil suggests that a large fiaction of the pesticide is associated wifii die suspended solids in nursery runoff. This determines that the downstream distribution of these pesticides is closely related to distribution of sediments, and that practices aiming to remove suspended solids from runoff will also be effective in reducing the level of these pesticides. 

Pyrethroid insecticides are widely used because of their high activity as an insecticide and low mammalian toxicity. Pyrethroids are in group 3, sodium channel modulators. The pyrethroids have a highly nonpolar nature, low water solubility, and high affinity to soil and sediment particulate matter. Natural pyrethrin is extracted from the flowers of Chrysanthemum spp., and its use was already known in China in the first century A.D. Pyrethroids, synthetic analogues of pyrethrin, have been produced since 1940 [26]. 

Pyrethroid Esters of Benzene Acetate. These insecticides have more extensive stmctural optimization in both acid and alcohol moieties. Fenvalerate [51630-58-17, a-cyano-(3-phenoxyphenyl)methyl (+)-(2R,5)"Ct"isoprop5i-4-chlorophenylacetate (24) d 1.17, vp 1.4 p.Pa at 25°C), a mixture of four isomers, is soluble in water to 0.3 mg/L The rat oral LD q is 450 mg/kg. Esfenvalerate [66230-04-4] is the (+)-2-(i, 5)-isomer (mp 59°C). The rat LD qS are 75, 458 (oral), and the rabbit dermal LD q is 2000 mg/kg. These pyrethroids are widely used general-purpose insecticides for field, vegetable, and fmit crops. 

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