Pyrethroids microbial degradation

Keywords Pyrethroid pesticide Organophosphate pesticide Acetylcholinesterase Microbial degradation Phosphotriesterases Fungi... 

Synthetic pyrethroids now account for at least 30% of the world insecticide market and are rapidly replacing other agricultural chemicals for control of insect pests. Fenvalerate is one of the more widely used synthetic pyrethroid insecticides. It is derived from a combination of a-cyano-3-phenoxybenzyl alcohol and a-isopropyl phenylacetate ester. Technical fenvalerate is a mixture of four optical isomers, each occurring in equal amounts but with different efficacies against insect pests. Fenvalerate does not usually persist in the environment for >10 weeks, and it does not accumulate readily in the biosphere. Time for 50% loss (Tb 1/2) in fenvalerate-exposed amphibians, birds, and mammals was 6 to 14 h for reptiles, terrestrial insects, aquatic snails, and fish it was >14 h to <2 days and for various species of crop plants, it was 2 to 28 days. Fenvalerate degradation in water is due primarily to photoactivity, and in soils to microbial activity. Half-time persistence in nonbiological materials is variable, but may range up to 6 days in freshwater, 34 days in seawater, 6 weeks in estuarine sediments, and 9 weeks in soils. 

In laboratory microcosms, ira 5-permethrin was selectively degraded compared to the other diastereomer, cw-permethrin, by six bacterial strains [19]. These strains also preferentially biotransformed 15-cw-bifenthrin over their antipodal l/ -cw-enantiomers, which were more toxic to daphnids [19]. Enantioselectivity was more pronounced for cw-permethrin than for cw-bifenthrin, and was strain-dependent. The (—)-enantiomer of both pyrethroids was preferentially depleted in sediments adjacent to a plant nursery, suggesting that in situ microbial biotransformation was enantioselective [20]. Although all enantiomers of permethrin were hydrolyzed quickly in C-labeled experiments in soils and sediments, the degradates of both cis- and irara-permethrin s -enantiomers were mineralized more quickly than those of the 5-enantiomer, while degradation products of cA-permethrin were more persistent than those of the trans-isomex [185]. Enantioslective degradation of fenvalerate in soil slurries has also been reported [83]. These smdies underscore how enantiomer-specific biotransformation can affect pyrethroid environmental residues, the toxicity of which is also enantiomer-dependent [18-20]. 

Malghani S, Chatteijee N, Yu HX, Luo Z (2009) Isolation and identification of profenofos degrading bacteria. Braz J Microbiol 40 893-900 Maloney SE, Maule A, Smith ARW (1988) Microbial transformation of the pyrethroid insecticides permethiin, deltamethrin, fastac, fenvalerate, and fluvalinate. Appl Environ Microbiol 54 2874-2876... 

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