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Phytoremediation: Persistent Pesticides

' II

Prospects and Limitations of Phytoremediation for the Removal of Persistent Pesticides in the Environment
Qasim C h a u d h r y 1, Peter Schr6der 2, Daniele Werck-Reichhart 3, Wlodzimierz Grajek 4 and R o m a n Marecik 4 t Central Science Laboratory, Department for Environment, Food and Rural Affairs, Sand Hutton, York Y041 1LZ, United Kingdom z Institute of Soil Ecology, GSF National Research Center for Environment and Health, Neuherberg, Germany 3Dept of Stress Response, IBMP-CNRS, Strasbourg, France 4Department of Biotechnology and Food Microbiology, A. Cieszkowski Agricultural University of Poznan, Poland

Corresponding author: Qasim Chaudhry, Central Science Laboratory, Department for Environment, Food and Rural Affairs, Sand Hutton, York Y041 1LZ, United Kingdom; e-maih q.chaudhry@r
By early 1970s, most uses of DDT and other persistent pesticides had been banned in many countries, although some applications continued into the mid-1980s. A limited use of some of the compounds is still allowed in many countries; for instance, DDT is used in over 20 countries in Asia and South Pacific for the control of insect vectors of tropical diseases, such as malaria. Since banning of persistent pesticides, and introduction of relatively more biodegradable ones (OPs, pyrethroids), their levels in the environment have been declining slowly [10-12]. However, remnants of their former use can still be detected in virtually every environmental compartment around the world. The United Nations Environment Programme (UNEP) has identified twelve persistent organic pollutants that require urgent regulatory attention. Nine of these are pesticides (aldrin, chlordane, DDT, dieldrin, endrin, heptachlor, HCB, mirex, and toxaphene), whilst the other three include polychlorinated biphenyls (PCBs), dioxins and furans [13]. Traces of a number of pesticides (predominantly OCs) have even been detected in regions, such as the Arctic, where these chemicals were never used [14,15]. In addition to this diffuse contamination, serious risks of further environmental pollution exist in the form of huge stockpiles of obsolete pesticides in many countries. The Food and Agriculture Organization (FAO) of the United Nations has estimated that at least 100,000 tons of unwanted pesticides are stored in developing countries, of which around 20,000 tons are in Africa (Fig. 1). Similar stockpiles exist in some countries of the Central and Eastern Europe, such as Poland [16,17], Latvia [18], and Bielarus [19]. In many cases, pesticide containers had been stored in the open or in underground bunkers. The deterioration of containers over time led to leakage of pesticides and contamination of soil and water in the immediate vicinity, and subsequently in areas far from the storage sites [20,21]. The unwanted pesticides mainly include both OCs (DDT, dieldrin, HCHs), and OPs (parathion, methyl-parathion, dichlorvos and monocrotophos). The FAO has estimated the cost of removing pesticide from Africa, and transporting and incinerating them in the EU at $3,500 to $4,000 per ton [22]. For most developing countries where obsolete pesticides are stockpiled, such costs are prohibitively high, and there is a need

DOI: Abstract. The environmental problems that have arisen from

the use of persistent pesticides in the past, and potential sources of further contamination have been discussed. The potential and limitations of phytoremediation for removal of pesticides in the environment have been reviewed. The enzymatic processes in plants that are known to be involved in phytodegradation of pesticides, and possibilities for enhancing them have also been discussed.
Keywords: Carbamate; contamination; environment; orga-

nochlorine; organophosphate; persistent pesticides; phytodegradation; phytoremediation; plant uptake



The widespread use of synthetic organic pesticides started after the 1940s. A number of potent and broad-spectrum organochlorine (OC) and organophosphorus (OP) insecticides were developed between 1939 and 1950. These were followed by the development of carbamates and pyrethroids in the next decade. During this period, synthetic pesticides were widely used for protecting crops and controlling disease vectors throughout the world, especially in developing countries in the tropical region [1]. Unfortunately, many of the early OCs and OPs were developed with little regard to problems that resulted from their large-scale use. Not only were there numerous incidents of acute toxicity in the short term [2], but also that residues of some persistent pesticides lingered on in the environment decades after abandoning their use (Table 1). Their bioaccumulation and bioconcentration in the food chain has since posed long-term risks to non-target species, including humans. Some persistent pesticides in the environment have been linked to disruption of endocrine hormones, increased risk of cancers, dysfunction of the immune system, and reproductive and developmental abnormalities in a number of aquatic and terrestrial species [7-9]. The widespread use of persistent pesticides also led to the development of new pests and diseases, and selection of resistance in a number of pest species.


ESPR - Environ Sci & Pollut Res 9 (1) 4 - 17 (2002) 9 ecomed publishers, D-86899 Landsberg, Germany and Ft. Worth/TX, USA ,, Tokyo, Japan 9 Mumbai, India * Seoul, Korea

18 C ~ r Mirex Atdrin Oielddn OC.4 c.9 years (HCB) 5.5 5.' Aldrin \i CH 2 Cl Cl CI Cl cl Dieledrin \[ CH 2 ESPR .73 3. cyclodiene 5 years (dieldrin) "CI CI Cl 6.7 to 22.Environ Sci & Pollut Res 9 (1) 2002 5 .2 C'\l Cl Endrine Toxaphene OC. cyclodiene Up to 12 years 5.76 CI CI~CI CI" HCB y Cl "CI DDT DDE OC 10 to 15 years 6.79 CH2 Toxaphene Mirex OC Up to 10 years 7.Phytoremediation Table 1: Persistent pesticides and their transformation products Persistent Pesticides HCB y-HCH OC 2. camphene 100 days to 12 years 5.78-6.69 ~ Cl/ ~"C I Cl DDT Endrine OC.19 5.

[4.Persistent Pesticides Table 1 : Persistent pesticides and their transformation products (cont'~ PestiCides/transformation product :: Chemical class Heptachlor Phytoremediation Persistence [3] Up to 2 years Log K=.10 Chemical StructUre T OC Cl\ Cl 0.81 O-.47-6.5. cyclodiene 1 year 6.Environ Sci & Pollut Res 9 (1) 2002 . High = half life >100 days 6 ESPR .70 Endosulfan Parathion OP 14 days 3.C--~I--CH3 Carbaryl Dimethoate OP 7 days 0. ~CI Cl c cis and trans Chlordane Endosulfan OC 50 days 4.6] 5.2 CI Heptachlor Chlordane OC.74 s H3C\ \o~P~ H~C~O/ II H2 H /C~ .00 c. Medium = half life 30-100 days./m~ S C~ ~"CH~ II o Dimethoate Low = half life <30 days.83 O" Parathion Carbaryl Carbamate 10 days 2.

run-offs and drainage. degradability by micro-organisms and uptake by aquatic and terrestrial species including plants. mostly OPs and their oxons (diazinon. The main emphasis until now has been to use plants with natural ability to hyperaccumulate inorganic pollutants. mecoprop. and tend to accumulate in relatively cooler regions that may be far away from the source where they were used. When released into the environment. isoproturan. and become partitioned between different geo. chemical reactivity. and precipitate back to land and water in the form of snow. are dispersed over a wide range in the environment. such as volatility. methyl-parathion). The most frequently detected pesticides in rainwater in Europe were HCHs. DDT and lindane).g. The process is dependent on climatic factors and usage of pesticides in the region.29]. MCPA. were present in fog-water [31]. and removal of their residues from contaminated environments. the use of plants to clean up contaminated environments has gained scientific credibility over the last few decades. pesticides disperse through volatilisation. and that their traces are detectable in almost every environmental compartment. the presence of highly persistent pesticides (half-life >6 months in soil) in run-offs may not pose a sign!ficant hazard to the environment [25]. In general. have now become a ubiquitous part of our environment. pesticides with Kd greater than 3. some samples were found to contain concentrations in the range of microgram per litre. however. 1 : Regions in Africa where obsolete pesticides have been stockpiled. dichloprop. distribution between polar and non-polar phases (log Kow) and between soil and water (Kd) [23]. have been shown to be more extractable from soil than others. chlorpyrifos. Although known for centuries. absorption and adsorption. 2 Diffused Contamination of t h e E n v i r o n m e n t lives of less than 3 months. terbuthylazine and aldrin [30]. and/or half- ESPR . Although most pesticides detected were below 100 ng/1 (permissible limit for drinking water). on the other hand. most pesticides used on land end up in aquatic environments. followed by atrazine. atrazine. The range and degree of environmental contamination is. Most semi-volatile pesticides tend to become concentrated in atmospheric water. DDT and dieldrin. Suffice to say that a number of man-made pesticides. as well as some newer pesticides (e. The technology. simazine) that are relatively more water soluble and thus more mobile in the environment [28. and environment-friendly methods for the safe disposal of remaining pesticide stocks. however.g. could also offer benefits in cleaning up the environments contaminated with hazardous organic pollutants such as pesticides. reproduced with permission from the Food and Agricultural Organization (FAO) of the United Nations for low-cost. aqueous solubility. rain or fog [26. The semi-volatile pesticides.Phytoremediation Persistent Pesticides Fig. DDT. unless used repeatedly. may not leach into the underground water [25]. malathion.g. simazine. A study in USA showed that traces of many pesticides. such as DDT and HCHs. and seepage and It is outside the scope of this review to cover the full extent of contamination of the global environment by persistent pesticides. Once in the environment.Environ Sci & Pollut Res 9 (1) 2002 7 . the persistence of a pesticide is dependent on its chemical stability.and bio-phases. Through the volatilisation and condensation cycle. Depending on their physico-chemical properties. such as methyl-parathion [24]. Some pesticides. The pesticides frequently detected in rainwater are the compounds that were used in the past (e. dependent on a number of environmental factors and physicochemical properties of a pesticide. Also.27]. such as toxic heavy metals. e. leaching.

The studies showed that concrete walls offered a poor barrier to pesticide diffusion from the dumps.and microbial-degradation. Most fungicides used in the EU region have been regarded as not persistent enough to have a significant impact on estuarine and marine environments. The bioaccumulation patterns of OCs by aquatic species have also been shown to differ with the depth of water. However. and also due to banning and restricting the use of persistent pesticides in Poland [16. and the internal and external surface was insulated with tar before placing it underground. whereas propiconazole was moderately persistent (half-life around 200 days) [47]. the triazole fungicides. These stocks of pesticides are scattered throughout the country in warehouses and on individual farms. Pesticides undergo a number of degradation processes during storage. and that only few of the samples did not contain HCBs or chlordane [51]. The main pesticides of concern in the dumps include chlorinated hydrocarbons. The analysis of OC pesticides in water [34.42]. A typical example. in areas that were periodically flooded. or near a source of drinking water.000 such sites may exist around the country. Over 2. 32 tons of pesticides were transferred from two sites to a new specially built store. It is.000 ton of highly contaminated soil were also transferred to the new site where pesticide residues were rinsed into a retention and evaporation tank to allow environmental. with a stockpile of up to 12. transportation and marketing sectors. has already led to severe environmental problems in Poland [50]. Some of the growing stocks of pesticides in Poland were dumped in waste stores built during the 1970s. mixing. These reactions reach equilibrium after some time. up to 1.35]. Bering Sea and Chukchi Sea. According to an estimate. marine species [37-39] and their products such as cod liver oil [40] has been used to assess the levels and patterns of pollution of the marine environment. due to its leaching into ground water [49] 8 ESPR . which reflects the situation in some countries of the Central and Eastern Europe is Poland. and relatively smaller amounts of carbamates and phosphoric acid esters. as many were built without permission from the authorities. river. reflect dispersion of semivolatile compounds from tropical to temperate regions. the bio. non-insulated ground pits were used as dumps. In addition to being poorly constructed. has been regarded as an important environmental breakdown product of DDT. lake. According to an estimate. around 65 tons of unwanted pesticides were moved to a safer unit [53]. organomercurial and organoarsenical compounds. With a space of I to 10 m 3.Environ Sci & Pellut Res 9 (1) 2002 . and during and after application. A typical dump was built of concrete rings. industrial. and so far no data are available on the specific percentages or the effects of degradation products resulting from breakdown of pesticides. nevertheless. of which up to 50% may be DDT [54]. rivers. DDT and metabolites have been reported to show a decreasing trend from north to south [36]. a DDT Aldicarb Carbaryl Diazinon Aldrin Fonofos Parathion Malathion Carbosulfan Thiocarb DDE. The widespread use of persistent pesticides in the 1950s. Indeed. with the deepsea biota showing much higher burdens compared to surfaceliving species of the same region [43-45]. The main transformation or degradation products of pesticides have been given in Table 2. The distribution patterns of different OC pesticides have been reported to differ in surface and core sediments from the Gulf of Alaska. sediments [36]. and in 1995. DDA (a) AIdicarb sulfoxide. Similarly. in a way similar to that of soil [45].0008. and their traces in drainage canals and river samples could be linked to known agricultural usage of the compounds [46]. nitrophenols. DDD. flutriafol. the findings that concentrations of some OC pesticides in tropical fish were lower than those in fish of the temperate regions [41. aldicarb sulfone 4-hydroxy carbaryl Hydroxy diazinon Dieldrin Fonofoxon Diethylthiophosphate and p-nitrophen01. The base and top lid were also made of concrete. together with accidental releases from agricultural. of which up to 12000 tons are stored in underground bunkers or 'tombs'. The exact number of such dumps in Poland is not known. Compared to a uniform distribution of HCHs and HCB. well known that some pesticides could be degraded to still active pesticides [48]. aminoparathion Malathion carboxylic acid Carbofuran Methomyl (a) DDA (2.000 ton pesticides passed their expiry date every year during the 1980s alone. 1-2 meter in diameter and 1-3 meter high. around 5. A recent study has shown that all 59 soil samples collected in Poland during 19901994 were contaminated with DDT and metabolites. most dumps were designed to store between 1 to 10 tonnes of chemicals [16].2-bis(chlorophenyl)acetic acid). where up to 60. On the basis of chemical analysis of samples from 128 sites. PCBs and HCHs. around 30% of the stored pesticides are OCs. Indeed. lakes.000 tons of unwanted pesticides may have been stored. in limestone and sandy formations. there are still substantial risks of pollution from stockpiles of obsolete pesticides in many countries. or local dwellings [52]. In some cases.and geo-phases of the deep-sea have been regarded the global sink for persistent semi-volatile contaminants. have been reported to be very persistent (around 2 year half lives at 10~ under laboratory conditions. pesticides get into surface and ground water.000 ton of hazardous chemicals. seas and oceans [32. many dumps were built at ground-water level. Added to this situation are the further risks posed by huge stocks of unwanted pesticides that have reportedly resulted from improperly controlled past system for imports. In 1994.Persistent Pesticides run-offs.33]. subsidies and distribution. Table 2: Environmental breakdown products of some Pesticides Pesticide Breakdown products [153] Phytoremediation 3 Potential Sources of Further Contamination Whilst banning or restricting the use of persistent pesticides has reduced further inputs into the environment. and leakage of biologically-active substances could lead to a hazard zone that could extend to the range of a few kilometres. epoxiconazole and triadimenol.17].

However. where DDT and lindane were among the most widely used pesticides in the past decades. There are also reports to indicate that similar problems regarding pesticide wastes exist in other neighbouring countries.0 mg/kg levels could be achieved within 8-40 min. or the levels of pesticides or their breakdown products in groundwater. initial trials using cement kilns in Pakistan. In some countries. tetradifon. The chemical oxidation processes currently used for pesticide degradation in wastewater include heterogeneous TiO z photocatalysis. and the resulting products may not always be safer than the parent compounds. For pesticide-contaminated soil or groundwater. the analyses did not include identification of the resulting degradation products.Phytoremediation Table 3: The chemicals most frequently found in pesticide storage bunkers in Poland [55] Persistent Pesticides of the biological methods that are available for in situ remediation of pesticide polluted environments. kelevan. compared to the disposal of unwanted stocks. In fact. and other countries. both fields have emerged as low-cost.p'DDT. or any. treatment with a chemical reagent such as a strong acid or alkali. the decontamination of polluted environments may be a very expensive and difficult task. record of the quantity or the nature of stored chemicals. such as Latvia [18]. Guidelines for the prevention and disposal of obsolete pesticide stocks have also been published by the Food and Agriculture Organization of the United Nations [62]. Certain enzyme preparations have also been reported DDT Chlorinated camphenes DMDT HCH and lindane Diene derivatives Hexachlorobenzene.and methyl parathion and diazinon.58]. Thermal desorption of pesticides bound to soil has been reported to be an effective technique for decontamination of OC pesticides. or incineration in cement kilns. and Bielarus [19]. or the OPs dimethoate.g. Over the years. endosulfan 42 20 11 10 4 13 list of the 10 most frequently found chemical groups in the dumps is presented in Tables 3 and 4 [55]. backed by well studied science. p. or catalytic reduction is usually sufficient to cause deactivation due to the cleavage of one or more bonds in the active ingredient. most physical and chemical methods for pesticide decontamination may not be feasible or practicable in a field situation. Around 75% of the stored pesticides are in solid form. Depending on the chemical nature of a pesticide. More than half of the sites have not maintained a complete. ethyl. where up to 5000 tons of unwanted pesticides may be stored. with only traces of ethyl-parathion detectable in some samples [63].1-1. However. environment-friendly technologies.Environ Sci & Pollut Res 9 (1) 2002 9 . 4 Available Options for Decontamination of Pesticides Organochlorines Inorganics Dithiocarbamates Phenoxyacids Organophosphorous Nitro-derivatives Carbamates Tar Quaternary amines Phthalimides 29-30 15-17 12-14 12-15 8-10 8 4 3-6 2 1 Table 4: The organochlorine compounds most frequently found in pesticide storage bunkers in Poland [55] A number of methods are available for the deactivation of undiluted and diluted pesticides in left over formulations and wastewaters. with removal efficiencies of >99%. At treatment temperatures of <277~ the removal efficacy of DDT was affected due to its breakdown to DDE [60]. most of the chemical methods may be prohibitively expensive or even impracticable. lindane. with the remaining in liquid formulations. dieldrin. Although disappearance of the pesticides was attributed to degradation by lime at higher pH. At soil treatment temperature between 260 to 538 ~ the thermal desorption of pesticides to 0. The soil samples from two of such sites in Greece have recently been analysed [63]. oxidants such as hydrogen peroxide or ozone. have highlighted operational difficulties and problems related to the control of emissions [59]. and this demands a thorough assessment ESPR . e. high-temperature incineration. ovotran. The other main option for disposal of unwanted pesticides involves degradation by thermal processes. and efforts have recently been made to develop a computerised inventory of the sites and the stored pesticides [56]. large quantities of unwanted pesticides were mixed with lime and buried underground during the 1970s. The two main biological methods for the removal and/or decomposition of pesticides include bioremediation using micro-organisms [64] and phytoremediation using plants [6567]. It has been estimated that the unwanted pesticides stored in Latvia occupy 1400 m 3 space at around 120 underground dumps [18]. There is an urgent need for strategies for the safe disposal of remaining stockpiles of persistent pesticides in developing and developed countries. Solar treatment of soil under plastic sheets has also been reported to enhance degradation of the OP pesticide quinalphos [61]. and for remedial actions to decontaminate polluted soil and groundwater to minimise the risk of further environmental pollution. ozonation or treatment with Fenton's reagent (Fe § and H202) [57. The results showed no detectable residues of the OCs aldrin.

peppers. and the main route of uptake 10 ESPR .p'-DDT.Environ Sci & Pollut Res 9 (1) 2002 . DDE. Studies have shown a substantial translocation of heptachlor epoxide. Indeed. Thus xylem translocation of compounds with log Kow >3 may be severely limited in plants [76-78]. but no translocation of dieldrin in forage/pasture species from soil contaminated with aged pesticide residues [90]. DDT. The compounds absorbed through plant roots may be translocated to other parts via xylem. the form of application also plays a crucial role in the uptake by plants. A recent study has shown that weathered soil residues of chlordane were accumulated in root tissues in the 12 food crops tested. The microbial transformations in the rhizosphere. but not in edible parts of tomatoes. Similarly. and Mirex in red mangrove (Rhizophora mangle L. and pole bean. The absorption of 14Cdimethoate by garden pea plants was greater than that of 14C-Malathion. must be considered an integral component of phytoremediation. and zucchini. climatic factors. which also translocated to aerial tissues in some cases [93]. and in particular the coefficient of partition (log Kow). Similarly. it has been reported that rape seedlings grown from seeds treated with lindane (7-HCH) [80]. The microbial activity in the rhizosphere also plays a crucial role in transforming pollutant chemicals [79].95 for the respective pesticides [96]. most importantly the physicochemical properties of individual compounds.62. It is evident from the published data that uptake and translocation of non-ionic pesticides varies greatly between plant species. trace amounts in edible parts of the bush bean and eggplant. The uptake of p. For semi-volatile pesticides. The residues of chlordane were detectable in edible root tissue in carrot. an aqueous fire-fighting foam containing OP-hydrolase has been reported to effectively degrade a number of OP compounds [68]. The transformation of The ability of certain plants to remove pollutant chemicals from the environment is well known. almost 90% of the pesticide was lost due to volatilisation. lindane. may only be limited in plants. the uptake of airborne xenobiotics by pine needles has been used as an environmental indicator of the presence of PCBs. absorbed from pesticide contaminated soil. More hydrophobic compounds tend to bind with lipid membranes in the roots. lindane and chlordane in the rooted aquatic plant Hydrilla verticillata (Royle) have been reported. more than 70% of 14C-etrimfos applied to bean and corn seedlings was lost due to volatilisation [85]. or maize plants grown in lindane-treated soil [81] absorbed and translocated the pesticide. Following foliage treatment of plants with methyl 14C-labelled fenitrothion. 38. but lack of translocation. The xylem translocation of the pesticides in the bean plants was negligible. DDT and DDE. and some species have been well studied for their ability to 'hyperaccumulate' inorganic pollutants such as toxic heavy metals [69-71]. with bioconcentration factors of 9. The uptake and translocation of persistent pesticides has also been studied in plants that grow in aquatic environments. lettuce. and in edible aerial tissues in spinach.) seedlings showed higher residues of dieldrin in hypocotyl and leaves of the seedlings than the other two pesticides [95]. mode of application. soil type. Thus the uptake and translocation of more hydrophobic pesticides. The residues of dieldrin. however. whereas factors that reduce wax viscosity enhance the uptake of non-polar compounds (high log Kow) [97]. which may aid root uptake and further degrada6on in plants. whereas only trace amounts were detectable in the shoots [91]. endrin and heptachlor were absorbed from contaminated soil and translocated in soybean plants. methoxychlor. Compared to this. and is dependent on a number of factors. whilst 14C-labelled HCB sprayed on Norway spruce stem cuttings was translocated to the needles [83]. HCB and H C H detected in foliage of the dwarf bean Phaseolus vulgaris were not dependent on pesticide concentration in soil. and potato. has been demonstrated [82]. The application of 14C-lindane along with nutrients to coffee plants resulted in absorption and accumulation of the pesticide in plant roots. the levels of p. ryegrass. Some plants have also been shown to absorb organic pollutants from contaminated soil. therefore. on the other hand. which may be translocated to other parts of the plant for enzymatic degradation or storage [72-74]. A number of studies have attempted to determine the absorption and translocation of persistent pesticides in plants.p'-DDE have been shown to be accumulated in the roots of lucerne. and corn. H C H and HCB in the environment [99]. the residues of DDT and aldrin absorbed from contaminated soil by sweet potato tubers were concentrated (50-100x) in the peel compared to that in the pulp [92]. optimal for those compounds that are only slightly hydrophobic (log Kow 1. water and air through root mass and leaf cuticle. A study of the translocation of dieldrin. a lesser translocation of T-chlordane. when applied to the foliage of potted coffee plants [84]. and plant species.15 and 1060. have a limited absorption through the leaf cuticle waxes. dandelion. and consequently their metabolic degradation. 5 Phytoremediation Phytoremediation by the foliage appeared to be through absorption of vapours [87].Persistent Pesticides to be useful in degrading pesticides. were mainly accumulated in roots of the grass Lolium perenne.p'-DDT by the cowpea Vigna unguiculata from soil treated with 14C-labelled pesticide has been reported [88}. For example. Whilst dieldrin. the pesticide was found to be stored in leaf cuticular waxes [98]. The uptake and accumulation of atrazine. but none of the plants translocated the compound to the shoot [89].8) [75]. the residues of DDT in the foliage were shown to result from vapour uptake of the pesticide [86]. DDE. For example.. beet. 6 Uptake of Pesticides by Plants The uptake of pesticides by plants is dependent on physicochemical properties of the compounds. Similarly. The absorption of HCB by plant root and leaf. which reflected the differences in aqueous solubilities and coefficients of partition (log Kow) of the two compounds [94]. The factors that increase hydration of leaf cuticle are thought to increase permeation of hydrophilic pesticides (low log Kow). Highly weathered soil residues of p. The hydrophilic compounds. The permeation from plant roots to xylem is.

and it is interesting to note that the same enzymes that are responsible for synthesis of plant defence chemicals also provide mechanisms for detoxification of those phytochemicals and synthetic pesticides in insects. it seems inevitable that useful catalysts for the detoxification of pesticides will also be found in plants.103]. which was the highest in microsomal fractions. For example.131]. nevertheless. but only slowly to the sulfone [130]. Thus the factors that enhance rhizospheric microbial activity should also be expected to increase the overall efficacy of pesticide phytoremediation. however. A number of early reports indicated that many insecticides acted as synergists of P4so-metabolised herbicides [110. most transformation products of pesticides in plants are not destined for excretion. such as desulfuration. such as cytochromes P4s0 [100]. hydrolysis 2. As the number of P4s0 genes in a small plant genome like that of Arabidopsis is close to 300. or in insoluble bound forms. and enzymes for oxidation of cyclodiene pesticides do not appear to be widely distributed in the plant kingdom. e.126]. aldrin and isodrin but not heptachlor were epoxidised in bean and pea root homogenates. isozafos and diazinon was later detected in maize or sorghum microsomes that was characteristic of a P4s0-catalysed reaction [114. The metabolism of different polychlorinated biphenyl (PCB) congeners by non-photosynthetic suspension cultures of rose [119] also appeared to involve cytochromes P4s0. this field now seems widely open for further investigations. Desulfuration at the thiono-sulfur apparently does not take place as readily as oxidation of thio-ether sulfur in plants [127-129]. Some oxidation of pesticides may take place in the environment due to photo-activated or metal-catalysed reactions with molecular oxygen. The epoxidase activity. 7 Degradation of Pesticides by Plants Persistent Pesticides It was later demonstrated that malathion. methidathion.105]. The enhanced levels of cytochromes P4s0 in insects have also been implicated in insecticide resistance [ 104. The ester group in carbaryl was not hydrolysed in bean plants. The cytochromes P4s0 and peroxidases in the microsomal fraction from tulip bulbs (Tulipa fosteriana) have been used in studying the metabolism of model xenobiotic compounds [118]. A small proportion of 14C-etrimphos applied to bean and corn seedlings was found to be hydrolysed to 6-ethoxy-2-ethyl4-pyrirnidinol and 2-ethyl-4. ESPR . 116. nematicide or fungicide detoxification by plant cytochromes P4s0 has never undergone a thorough investigation. and suggested the possible involvement of a peroxidase [109]. whilst none of the compounds was transformed in corn root homogenates [122].Environ Sci & Pollut Res 9 (1) 2002 11 .117]. Carbamate compounds are metabolised in plants through oxidation or conjugation. sulfur oxidation. as the reaction was inhibited by inhibitors of the mixed function oxidases. peroxidases [101] and flavin-dependent monooxygenases [102. and specific P4s0 isoforms from mammals and insects have been found to metabolise pesticide compounds [120-121]. including epoxide formation. Deactivation of OPs through hydrolysis or conjugation appears to be common in plants [127. conjugations 3. and for different carbamate compounds [124]. showed metabolism of heptachlor. but later studies on the soybean root nodule aldrin epoxidase casted doubts on the participation of a cytochrome P4s0 in the reaction. The metabolism of herbicides by cytochromes P4s0 in plants has been well documented since it constitutes a major determinant of herbicide tolerance and selectivity. such as oxidation. With the recent availability of recombinant enzymes. or N-dealkylation. and varieties of peas and maize [107]. although the compound was glycosylated and also transformed to some insoluble forms [125]. These microsomal enzymes. Three main reaction types are known to drive transformation of pesticides in plants: 1. dimethoate was shown to be hydrolysed in wheat and soy- Unlike animals. For example. Evidence. Rearrangements. and of the evolution of resistant weeds [106].6-pyrimidinediol [85]. ubiquitous in both animals and plants. Although mineralisation (complete decomposition) of pesticides is the desired end point in phytoremediation. A mechanism was proposed in plants.Phytoremediation pesticides in the environment. Degradative. The pre-treatment of pea plants with aldrin was reported to induce a higher rate of aldrin metabolism [108]. not as efficient as in animals.g. The alkyl sulfur. The most commonly observed degradation reactions involve oxidation of pesticides. Carbamate compounds with an aromatic moiety have been reported to be resistant to hydrolysis in plants [125. None of the preparations.128. Despite such evidence. Similarly. The oxidation of pesticides in plants is. which is parallel to mammalian cytochromes P4s0 catalysed desulfuration of organophosphate insecticides (P=S ---) P=O) with the release of atomic sulfur that tends to covalently bind to P4s0polypeptide [115]. is rapidly oxidised to sulfoxide. transformation of aldrin to dieldrin through epoxidation has been reported in vitro in root extracts from different species of beans. The OP compounds may be activated by certain transformation reactions in plants.111]. although the rate of transformation has been reported to differ in different plant species [123]. and also due to microbial activity in the rhizosphere. was stimulated by the addition of NADPH. insecticide. could result in products that are more efficiendy absorbed and translocated in plants. usually a few transformation reactions are sufficient to drastically change their biological activity. play a crucial role in biosynthesis and breakdown of a wide variety of endogenous and exogenous compounds through oxygenation or hydroxylation. or deactivated by O-dealkylation and hydrolysis. but not by peroxidase inhibitors. often indirect. for their involvement in the oxidative transformation of other pesticides has only been reported in few cases. The cytochromes P4s0 superfamily is composed of at least 215 families. Biological oxidations of pesticides are catalysed by a number of enzymes. Synthetic. but instead remain in plant tissues either in conjugated soluble forms. on the other hand. The desulfuration of malathion. terbufos and its oxidative metabolites formed in the soil behaved as mechanism-dependent inactivators (suicide substrates) of cytochromes P4s0 involved in the detoxfiication of sulfonylurea and several other classes of herbicides [112-114].

146]. Unlike recent concerns over genetically modified food crops. dehydrochlorination of DDT may result in equally toxic products. This was followed by reports that suggested detoxification of other herbicides via glutathione conjugation [145. success of the technology would depend on selection of those plants that can grow in environments heavily contaminated with organic chemicals. and the terrestrial plant Pueraria thunbergiana [140]. Atrazine was the first shown herbicide to be conjugated with glutathione in plants [144].2-bis-(4chlorophenyl)-acetic acid] to acylglucoside has been reported from a soluble fraction of cultured soybean cells [155]. Through selective manipulation of a plant's genetic makeup. The transformation appeared to take place in a non-enantioselective manner with o. it is important to identify those areas that are of direct or indirect relevance to phytoremediation of pesticides. and may not lead to their detoxification. unlike animals. less common than oxidation [130]. which binds a wide variety of electrophilic compounds to the tripeptide. in descending order of frequency.and p. plants do not have any specialised organ (such as liver) for detoxification of xenobiotics.p'. The rate of in vitro glutathione conjugation of the fungicide PCNB (quintozene) was only intermediate to low as compared to that of the herbicide fluorodifen. Extracts from spruce needles have been reported to contain GST activity that catalysed conjugation of pesticides [149].p'. although EPTC can be also detoxified via a glutathione conjugate in millet and corn [154]. and an association between glutathione-transfer mediated and glucosyl-dependent detoxification pathways has been proposed [152]. butylate. the capability to remove and/or degrade pesticides may be further enhanced in a number of ways. if not all. with almost a quarter of the pesticide covalently bound in Elodea canadensis. and that the transformation reactions may take place at a far slower rate in plants than in animals. However. by isomerisation and changes in chirality that influence their biological effects [153]. The glucosylation of carbaryl h a s been reported following its oxidation in bean plants [125]. herbicide resistance and heavy metal detoxification in plants has been discussed by Rennenberg [142] and Lamoureux and Rusness [143]. 8 Enhancement of Phytoremediation In the wake of the recent surge in biotechnological sciences. however. The synthetic routes to the detoxification of xenobiotics in animals mainly involve catalysis by the enzyme glutathioneS-transferases (GST). Phytoremediation 152]. They may. however. It is unlikely that the sulfur stems from a former glutathione conjugation reaction and subsequent degradation [153]. on the basis of current knowledge. For example. However. and oxidation to malaoxon. The hydrolysis of malathion to dimethylphosphorothionate and dimethylphosphorothiolothionate. or that have been engineered to express a useful enzyme. A high rate of PCNB conjugation and metabolism has also been reported in onion [150]. a pesticide-degrading enzyme from another spe- 12 ESPR . with some species showing particularly high activities of the enzyme [156]. plants that can be utilised in the degradation of persistent pesticides in the environment. These processes may. The reductive dechlorination of p. terbufos and phorate have been shown to be converted to their respective sulfoxides. a phytoremediation approach that utilises non-food plants with enhanced ability to cleanup pesticide-polluted environments may have a beneficial effect on the public perception of biotechnology. In fact.Environ Sci & Pollut Res 9 (1) 2002 . such as DDE. most conjugation reactions seem to be limited to sugars.p'-DDD as the only resulting products. peptides and sulfate.Persistent Pesticides bean grains in vitro and in vivo with cleavage of the P-C-S bond at P-S position [132]. It is. the process did not appear to be driven by microbial activity. it has to be concluded that glutathione and glucose conjugations are not primary detoxification mechanisms for majority of persistent pesticides. The absorption but lack of metabolism of DDT by barley plants has been reported [136]. For example. Generally. A study of many plant species and cell cultures showed that O-glucosyltransferase activity. however. The information on pathways for phytodegradation of persistent pesticides is limited and patchy. The role of glutathione in the metabolism of pesticides. EPTC. which acts on DDA and other xenobiotics. glutathione. Organochlorine pesticides are apparently quite recalcitrant to metabolism both by terrestrial plants [130] and marine phytoplankton [135]. A number of glucoside conjugates of pesticides have been reported in plants [151.p'-DDT has also been reported in the aquatic plant Elodea canadensis. however. The reductive transformation of pesticides in plants is. It is equally important to note that. as pesticide transformation reactions in plants are not aimed at products that are to be excreted. followed by hydrolysis to malaoxon mono. As irradiation at 300 krads did not stop transformation of DDT. is widespread in the plant kingdom. The resulting hydrophilic conjugates are broken down subsequently and excreted as mercapturic acid conjugates via the kidney [141]. whereas DDD and DDE but no DCBP was detected in cottonseed [138] and in extracts of cotton leaves [139]. the transformation reactions that expose one or more functional groups in pesticides are followed by conjugation to a sugar moiety.148]. Some compounds have also been reported to be altered intrinsically. The dealkylation of substituted amide and amino groups in plants has also been demonstrated by the isolation of N-hydroxymethyl intermediates of dicrotophos [134] and carbaryl [125]. such as glucose.and o. The metabolites of DDT detected on leaf surface of apples included traces of DDD and 4.9. The unstable enzyme had a molecular weight of around 50 KDa. has been demonstrated in wheat grains [133]. with isoelectric point of around pH 4. the enhanced GST activity in some plants has been associated with resistance to herbicides [147.4' dichlorobenzophenone (DCBP) [137].and di-acids. be enhanced by using selected plants that have higher levels of pesticide degrading enzymes. and there is a need for further systematic studies to realise the full potential of plants for use in phytoremediation of pesticide contaminated environments. evident from the published examples that useful metabolic pathways exist in most. play a role in downstream metabolic reactions of the breakdown products of pesticides. In either case. The isolation of an enzyme that catalysed conjugation of the DDT metabolite DDA [2.

associated with insecticide resistance in Heliotbis virescens. it would be possible to develop plants with the capability to bind large quantities of a specific pesticide. or a group of pesticides. which can enhance uptake and transformation by plants. this has had a little impact on phytoremediation until now. Through appropriate design of immunogens. and expressing functional proteins in transgenic plants. or the expression of an already present enzyme may be enhanced. As microbial activity in the rhizosphere is known to aid the release of bound pesticide residues in soil. are known to induce root proliferation in plants. The newly emerging plant 'hairy root' technology. it may even be possible to engineer a groupspecific antibody fragment that binds to a number of structurally similar chemicals.165]. A mammalian cytochrome P4s0 (2El). for example energy generation.Environ Sci & PoIlut Res 9 (1) 2002 13 . e. the antibody fragments used were reactive to a protein or peptide.161]. The genes that code for some of the enzymes have been the focus of studies for incorporation in bacteria and plants for subsequent use in bio/phytoremediation.Phytoremediation cies (such as a bacterium or insect) may be engineered in a plant. low maintenance. in most cases. this 'subunit-antibody' can be expressed in plants to enhance their capability to bioaccumulate large quantities of the compound. However. It is only recently that the applicability of this technique to small-molecule organic chemicals (haptens) has been appreciated. Libraries of large repertoires of cloned scFv antibody genes that have been constructed to 'display' antibody combining sites on the surface of recombinant phage. provide a means for rapid screening of a given analyte [160]. and plant pathogenic viruses [162. In the past decade. has been engineered in bacteria. For example. tobacco and baculovirus for evaluation in remediation of pesticides [158]. phytoremediation could at best be useful as a long-term strategy. and also to increase the uptake and debromination of ethylene dibromide [159]. may also be very useful in removing pollutants from pesticide-contaminated water [171]. the technology would probably have little impact in situations where low levels of a pesticide were widely distributed in the environment. it should also be possible to enhance a plant's ability to absorb and bind a specific pesticide by incorporating a gene for an anti-pesticide antibody fragment. 9 Limitations of Phytoremediation As discussed above. phytoremediation has its own limitations. These limitations require integration of phytoremediation with other more immediate cleanup options. Also. This has also been reported to enhance the uptake of PCBs and other pollutants by the infected plants from soil and groundwater. The amount of knowledge generated in plant biotechnology in recent years is enormous.163]. has been expressed in tobacco plants. These few but successful examples demonstrate that functional scabs against organic chemicals can be expressed in transgenic plants. The anti-atrazine antibody expressing plants have been reported to effectively bind the herbicide in soil/water [166]. are known to confer enhanced detoxification of insecticides [157]. This is because plant growth is dependent on a number of environmental and climatic factors. the role of vegetation and plant biomass as an absorbent and a long-term sink for diffused pesticides must not be underestimated. Other strategies to enhance phytoremediation ability in plants have been directed at increasing the root mass. A similar approach could also pave the way for development of plants that express binding sites for several structurally-similar pesticides. phytoremediation may be the only practical and economical in situ technique that can be used to remove pollutant chemicals. which could also increase the uptake of certain pollutant chemicals. Through incorporation of the relevant gene. and through foliage to compounds that are not hydrophilic. phytoremediation offers a low-cost. as well as more economical utilisation of the biomass produced for non-food purposes. Some strains of Agrobacterium tumefaciens. such as nematodes [160.g. which has potential applications in secretion of natural products and recombinant proteins. The development of 'generic' antibodies reactive to a Persistent Pesticides number of OP pesticides has already been demonstrated for analytical applications [169]. a bacterial parasite of plants. The single chain variable fragment (scFv) of immunoglobulins contains the combining site of an antibody towards a given analyte. environment-friendly and renewable resource for the remediation of contaminated environments. availability of water and nutrients. Even under the most favourable conditions. for example pesticide-laden soil or ground water. screening scAb gene libraries [168]. To date. In some situations. etc. and were aimed at developing plants that are resistant to pests and diseases. there have been only two reports on the expression of anti-atrazine and anti-paraquat antibody fragments in transgenic tobacco plants [164. The uptake and translocation of organic pollutants from soil through the plant root may be limited to compounds that are not highly hydrophobic. Certain enzymes in insecticide-resistant insects. The uptake and retention of organic pollutants by plants is another major limiting factor in phytoremediation of contaminated soil and water. esterases and cytochromes P4s0. By combining expertise in these fields. plant growth and removal/degradation of pesticides may not exceed a certain rate. This has been shown to enhance the metabolism of trichloroethylene to up to 640 times in the transgenic tobacco plants. However. known to oxidise a wide range of halogenated hydrocarbons including trichloroethylene. a cytochrome P4s0 (CYP9A1). A number of reports have indicated successful incorporation of scFv antibody genes in plants. and there are many more yet unexplored avenues that can be pursued to engineer or enhance a particular pathway for the phytodegradation of persistent pesticides in the environment. Whilst the advancement in biotechnological sciences has revolutionised a number of areas of conventional science. possibly due to an increased rate of cell division and root mass [170]. ESPR . There is also a need for finding ways to enhance the absorption and degradation of pesticides in plants. there have been great technological leaps in the fields of designing immunogens for haptens [167]. a combination of microbial bioremediation and phytoremediation is likely to be more successful in the field. from a polluted environment. soil type and pH. However. such as soil or water. Even when large amounts of pesticides were present in a given environmental compartment. Whilst the main focus of research has been to select plants with ability to 'hyperaccumulate' or biodegrade pollutant chemicals.

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