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Dissipation of β-cyfluthrin by two fungi Aspergillus nidulans var. dentatus and Sepedonium maheswariumIrani Mukherjee a & Archana Mittal aa Division of Agricultural Chemicals, Division of Nematology ,Indian Agricultural Research Institute , New Delhi 110012, IndiaPublished online: 02 May 2007.

To cite this article: Irani Mukherjee & Archana Mittal (2007) Dissipation of β-cyfluthrin by twofungi Aspergillus nidulans var. dentatus and Sepedonium maheswarium , Toxicological &Environmental Chemistry, 89:2, 319-326, DOI: 10.1080/02772240601010089

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Toxicological & Environmental Chemistry, Apr.–June 2007; 89(2): 319–326

Dissipation of b-cyfluthrin by two fungi Aspergillus

nidulans var. dentatus and Sepedoniummaheswarium

IRANI MUKHERJEE & ARCHANA MITTAL

Division of Agricultural Chemicals, Division of Nematology, Indian Agricultural Research

Institute, New Delhi 110012, India

(Received 23 July 2005; revised 24 April 2006; in final form 8 September 2006)

AbstractTwo fungal species, namely Aspergillus nidulans var. dentatus and Sepedonium maheswarium werescreened for elimination study of �-cyfluthrin, a synthetic pyrethroid insecticide. The highestelimination of �-cyfluthrin, from the media was observed by A. nidulans var. dentatus a toxic fungi(T1/2 11 days) as compared to S. maheswarium, which is an egg parasitic fungi (T1/2 19 days).Two major degradation products were isolated after 20 days of growth of fungi, which wereidentified as 4-flouro-3-phenoxybenzaldehyde and 3-(2,2-dichlorovinyl)-2,2,dimethylcyclopropanecarboxylic acid.

Keywords: �-Cyfluthrin, Aspergillus nidulans var. dentatus, Sepedonium maheswarium

Introduction

�-Cyfluthrin is a mixture of two enantiomers, S-(�-cyano-4-flouro-3-phenoxybenzyl) (1R)cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate and the corresponding (R)and (1S) cis-isomer and (S) (1R) trans-and (R) (1S) trans-isomers in 1 : 2 ratio of the parentcompound cyfluthrin. This photostable synthetic pyrethroid [1] has an ester and etherlinkage in addition to a dichlorivinyl group attached to a cyclopropane moiety (Figure 1, I).�-Cyfluthrin is unique among the synthetic pyrethroids [2] because of the presence offluorine atom in the molecule, which imparts special character to the compound. It is anon-systemic, contact insecticide with wide spectrum of activity against Lepidoptera,Coleoptera, and Hemiptera in cotton, fruits, vegetables, and cereals.

The consumption of synthetic pyrethroids has increased significantly with the decline inthe use of organochlorine pesticides like lindane and endosulfan, which were being used for

Correspondence: Irani Mukherjee, Division of Agricultural Chemicals, Division of Nematology, Indian Agricultural ResearchInstitute, New Delhi 110012, India. E-mail: mukrj_irani@yahoo.com

ISSN 0277-2248 print/ISSN 1029-0486 online � 2007 Taylor & FrancisDOI: 10.1080/02772240601010089

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the control of insect pests in various crops. The synthetic pyrethroids represent the mostpopular class of insecticides today. The presence of pesticide residues in vegetables andfruits above the maximum limit is of concern to human health due to the toxic nature of thepesticides.

The residues of �-cyfluthrin have been estimated on various crops like eggplant [3,4],gram [5], okra [6], tomato [7], mustard [8], sorghum [9], and cotton [10]. Laboratorystudies have indicated that due to low mobility it does not transport beneath the sub-soilsurface [11]. The compound is also being used in public health for the control ofmosquitoes and houseflies [12] and cockroaches [13]. There are reports of the use of fungi[14,15] and enzymes [16] for the degradation of �-cyfluthrin.

In this study, an attempt is made to explore the use of fungi isolated from nematodeinfested agricultural field, as a tool for the degradation of �-cyfluthrin, under laboratoryconditions.

Materials and methods

Chemicals

Reagents (solvents): acetone, hexane, and dichloromethane; Adsorbents: neutral alumina,Florisil. Drying agent: anhydrous sodium sulfate.

All the chemicals were obtained from SD Fine Chem Ltd Mumbai, India. The solventswere distilled before use.

NMR was recorded on Varian model NMR (60Hz) and FT-IR on Impact 400-Nicolet.

Analytical standard

Analytical standard of �-cyfluthrin (97.8%) was procured gratis from Bayer India Ltd.The stock solution of �-cyfluthrin was prepared in hexane at 1mgmL–1 and stored at 4�C.Working standards were prepared by appropriate dilutions.

I

III II

C

O

O

CH

CN

O

F

Cl

Cl

C

O

OHCl

Cl

O

F

OHC

Figure 1. �-Cyfluthrin (I), 4-fluoro-3-phenoxybenzaldehyde (II), and 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (III).

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Isolation of culture – Sepedonium maheswarium

The culture of S. maheswarium was isolated from the egg masses of root knot nematodes,Meloidogyne incognita infecting brinjal [17]. The fungus was isolated by surface sterilizingthe egg masses with 1000 mgmL�1 mercurous chloride and ethanol (95%) for 1min. Theegg masses were further rinsed with sterile water three times. The surface sterilized eggmasses were placed on petri-dishes containing potato-dextrose agar (PDA-mediumconstituents, 200 g potato, 30 g dextrose, 20 g agar dissolved in 1L water) medium underlaminar flow. The petri dishes were incubated in the BOD incubator at 25þ 2�C for 7 days.The fungus isolated from the eggs through repeated sub-culturing and single sporeisolation was observed. The fungal colony was purified for identification and characterizedas S. maheswarium by ITCC, Division of Plant Pathology, IARI, and New Delhi.The egg-parasitic nature was confirmed through in vitro tests. Percentage of egg-parasitization of S. maheswarium was 70%. Most of the eggs in the egg masses wereaffected with this fungus.

Characterization of fungus

Sepedonium maheswarium is a filamentous fungus, the septate hyphae, simple or branchedconidiophores and conidia are visualized. Condia are large celled (7–17 mm) and terminallylocated on the conidiophores. They are solitary hyaline to amber in color and globose toavoid in shape. These conidia are typically thick walled, rough and knobby in appearance.These were isolated from root knot nematode, M. incognita infecting brinjal crops.

Isolation of culture – Aspergillus nidulans var. dentatus

The cultures of A. nidulans var. dentatus were isolated from the soil rhizosphere of root–knotnematode infested brinjal plants. The soil (1g) was dissolved in sterile water and furtherdiluted serially to 1000 times. One aliquot of soil water suspension was pipetted out intopetri dish containing PDA amended with a 0.001mg of streptomycin sulphate. The petridishes were swirled gently to spread the suspension and the liquid medium allowed to cooland then incubated at 25þ2�C for 7–10 days. The fungi were identified as A. nidulans var.dentatus by ITCC, Division of Plant Pathology, IARI, and New Delhi.

Characterization of fungus

Aspergillus nidulans var. dentatus is a typical soil fungus with a worldwide distribution. It hasbeen reported as a causative agent of aspergillosis in humans and animals. This fungus hasconidial heads, short columar (up to 70� 30mm in diameter) conidiophores are usuallyshort, brownish and smooth walled. Conidia are globose (3.0–3.5 mm in diameter) andrough walled.

The fungi A. nidulans var. dentatus (toxic) and S. maheswarium (egg-parasitic) were grownand maintained in potato dextrose broth medium containing dextrose 20 g, potato 200 gand water 1L.

Pesticide inoculation and degradation

Technical grade �-cyfluthirn was further purified by silica gel column chromatography(99þ% purity). All other chemicals used were of the highest analytical grade. Both thefungi were grown in 150mL Erlenmeyer flasks containing 50mL of potato dextrose brothmedium and incubated for three days at 25�2�C.

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All conical flasks (150mL capacity) were plugged with cotton and autoclaved at 15 atmspressure for 30min. �-Cyfluthrin of 20mg dissolved in acetone was added to each of the 84flasks under sterilized conditions of Laminar flow hood and allowed to evaporate underroom temperature. Then 50mL of the potato dextrose broth medium was added to eachflask already containing the pesticide. The experiment was carried out in triplicate.

Five sets of the experiment were maintained, set I: (MþF1) potato dextrose brothmediumþ fungus culture�A. nidulans var. dentaus, set II: (MþP) potato dextrose brothmediumþ �-cyfluthrin, set III: (MþF1þP) potato dextrose broth mediumþ funguscultureþA. nidulans var. dentatusþ�-cyfluthrin, set IV: (MþF2) potato dextrose brothmediumþ fungus cultureþS. maheswarium, set V: (MþF2þP) potato dextrose brothmediumþ fungus cultureþS. maheswariumþ �-cyfluthrin.

The sets I, II, and IV served as control experiments. The sets III and V served astreatment. After incubation, the mycelial inoculum from fungus A. nidulans var. dentatuswas added to each flask (of sets I and III) and S. maheswarium was added separately to eachexperimental flask (sets IV and V). The pH of the medium recorded after the addition offungi and pesticide was 7.0.

Cultures were incubated further for different growth periods of up to 20 days afteraddition of �-cyfluthrin. A set of heat killed control samples were prepared by autoclavingthe cultures before adding �-cyfluthrin and were incubated along with the live culturefor the same period of time. Appropriate control experiments were carried out withun-inoculated medium. At intervals, samples in triplicate from control, heat-killed control,and live cultures were removed and acidified to pH 2 with 1N HCl.

Extraction

The flasks were taken out periodically on days 0, 1, 3, 5, 7, 10, 15, and 20 for the estimationof �-cyfluthrin. The medium was centrifuged and then filtered. The filtrate was diluted withsaline water (2%, 30mL) and further subjected to liquid–liquid partitioning thrice withdichloromethane (30mL). The mycelia residue left in the tube was transferred to a conicalflask, to which dichloromethane (20mL) was added and shaken vigorously for 15min in ashaker. The solvent was filtered through anhydrous sodium sulfate and stored. The processwas repeated again with 20mL dichloromethane. The combined organic layer was driedand evaporated under reduced pressure to remove all the traces of dichloromethane. Thesample was made up in hexane (10mL) and analysed by GLC.

Analysis

GC apparatus: the quantitative estimation of �-cyfluthrin was carried out using HewlettPackard gas liquid Chromatograph series II (model 5890) equipped with Ni63 electroncapture detector. The column BP-5 was megabore (12m� 0.52mm i.d.�1 m).

GC operating parameters

The analysis was carried out using a Hewlett Packard 5890 series II instrument. Thecolumn used was a megabore HP I (12m long�1mm film thickness�0.52 mm). Thecolumn temperature was maintained at 250�C while the injector port and the detector wereset at 260 and 300�C, respectively. The carrier gas nitrogen flow was maintained at20mLmin�1. The retention time of �-cyfluthrin was 5.26min.

The identity of the pesticide was further confirmed by carrying out the GLC using acolumn of alternate polarity on specifically, glass column SE-30 (2m�2mm i.d.) coated

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on Chromosorb WHP. The column temperature was maintained at 280�C and the injectorport and the detector were set at 290 and 300�C, respectively. The nitrogen gas flow was32mLmin�1. The retention time of the �-cyfluthrin was 7.23min.

A third column used for confirmation of the pesticide was megabore BP-5(30m� 0.52mm i.d.�1 mm). The conditions maintained were column temperature, at240�C and the injector port and the detector were set at 280 and 300�C, respectively. Thenitrogen gas flow was 30mLmin�1. The retention time of the �-cyfluthrin was 5.23min.

Synthesis of metabolites

4-flouro-3-phenoxybenzaldehyde (II) and 3-(2,2-dichlorovinyl)-2,2,dimethylcyclopropanecarboxylic acid (III). �-Cyfluthrin (1 g) was dissolved in methanol (30mL) refluxed withaqueous sodium hydroxide (100 gL�1, 20mL) for 2 h. The reaction mixture was cooled andextracted with dichloromethane. The crude mixture showed two products on thin layerchromatography (TLC). Column chromatography over silica gel, and successive elutionwith hexane and mixture of hexane: acetone yielded pure two compounds. 4-fluoro-3-phenoxybenzaldehyde (II, Rf 0.28), IR � cm�1 1725(s, C¼O); NMR–CDCl3 �: 6.76(m, 5H, Ar–H, C-5, C-20, 30, 40, 50, and 60), 7.52 (dd, J¼ 2Hz, 2H, C-2 and 4), 7.63 (s,1H, C-6), C-9.85 (s, 1H, D2O, CHO), m/z 243.

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (Farkas acid III, Rf0.13), IR: � cm�1 1780,COOH, 3200 (b, OH); NMR-CDCl3 �: 1.22 (s, 6H, 3�CH3),1.72 (s, 1H, CH–C), 2.22 (s, 1H, CH–COOH), 5.65 (s, 1H, C¼CH), 10.0(s, 1H, D2Oexchangeable), m/z 208.

Quantification

The concentration of �-cyfluthrin was calculated on the basis of a peak area from thecalibration curve. Standard solutions of different concentrations 0.1, 0.2, 0.5, 1.0, 1.5 and2.0 mgmL�1 of �-cyfluthrin were injected in the GLC and a calibration curve was drawn byplotting peak area versus concentration. Each injection was made thrice for all theconcentrations so as to obtain the linearity range of the pesticide.

Thin layer chromatography (TLC)

Thin layer chromatography was carried out on silica gel G coated glass plates usingacetone–benzene (1þ 9) as the developing solvent. The aldehyde was identified on TLCusing 0.1% phenyl hydrazine hydrochloride as a visualizing reagent. The acid was visualizedin an iodine chamber.

Results and discussion

Brinjal crop grown around the trans-Yamuna river belt of Delhi exhibited patchy andunthrifty growth [18]. The stunted plants were uprooted, and it was observed that majorityof the roots of the plants were galled. The roots were infected with adult saccate females ofroot knot nematode. However, the egg masses attached to the females indicated fungalinfection of eggs with conidia and mycelia of S. maheswarium and the rhizosphere soilshowed the presence A. nidulans var. dentaus.

The two degradative products were synthesized in the laboratory to serve as authenticsamples for quantification in the extract. Two metabolites of �-cyfluthrin weredetected which appeared below the spot of �-cyfluthrin on TLC, which were identified

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as 4-fluoro-3-phenoxybenzaldehyde (II, Rf 0.58) and 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane carboxylic acid (III), Rf 0.13) as are supported by the IR and NMR spectra.The NMR data of the Farkas acid (III) showed the presence of proton at �10.0, whichexchanged with D2O, confirming the presence of proton a carbonyl group. The peak in IRat 1780 cm�1 and a broad peak due to hydroxy group at 3200 cm�1 confirmed the presenceof a carboxylic unit. The NMR spectra of the 4-fluoro-3-phenoxybenzaldehyde (II)exhibited the presence of five shielded protons at C-20, 30, 40, 50, and 60 at � 6.76, twoprotons at C-2 and 4, at �7.52 and a deshielded proton at C-6 at �7.63, which was observedas doublet due to presence of electronegative fluorine atom, the aldehyde proton wasobserved as a singlet at � 9.85. Initially cyanohydrin is formed which is converted to �-cyano-4-fluoro-phenoxybenzaldehyde and in the plant system the aldehyde gets oxidized to4-fluoro-phenoxybenzoic acid. The identity of the compounds II and III confirms thehydrolysis of �-cyfluthrin.

4-Flouro-3-phenoxy-�-cyanobenzyl alcohol initially formed is converted to 4-flouro-3-phenoxybenzaldehyde by the loss of HCN followed by internal rearrangement of themolecule. The presence of aldehydic group is indicated by the appearance of pink colourwhen phenyl hydrazine hydrochloride is sprayed on the TLC plate. Structure of thealdehyde is confirmed by IR and NMR. The metabolites 4-flouro-3-phenoxybenzaldehydeand the 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid were not detectedin the samples on day-0, 3, and 5. This may be attributed to the fact that the amount ofmetabolites formed were below the detectable limit, or else both the metabolites remainconjugated to the sugar moiety in the fungus, as has also been reported in a case study ofcypermethrin in plants [19]. However, they were detected on TLC on day-10, indicatingthat after an incubation period of 10 days the metabolites were formed in sufficient amountto be visualized on TLC.

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (III) also termed asFarkas acid is documented as non-toxic metabolite. As in cypermethrin the fluorinatedanalog of 3-phenoxybenzaldehyde will be less toxic than the parent compound �-cyfluthrinLD50 oral rat 500mg kg�1 in polyethylene glycol, and 270mgkg�1 in xylene. Toxicityof 3-phenoxybenzaldehyde is documented in www.parijataagrochemicals.com/metaphenoxy.htm as LD50 oral rat 1500mkg�1 whereas, for cypermethrin it is 250,indicating that the degradation product is less toxic than the parent molecule.

Saikia et al. [15] studied the biodegradation of �-cyfluthrin with five fungal species,namely, Trichoderma viride strain 5-2, T. viride strain 2211, Aspergillus niger, Aspergillus

terricola, and Phanerochaete chrysoporium and reported five degradative products, two ofwhich are same as that observed in the present study.

The initial dissipation of �-cyfluthrin in PDA medium by day-3, recorded was 6.72%indicating that there was no slow dissipation of the pesticide in the medium (Table I).However, by day-20, 23.9% dissipation was recorded showing the medium has an effect onthe dissipation of �-cyfluthrin. In the treatments with the A. nidulans var. dentatus, initialdissipation recorded on day-3 was 16.6% which increased to 72.7% by day-20, while in thetreatment with fungus S. maheswarium, slow dissipation of 12.9% was observed on day-3,which later increased to only 52.7% by day-20. This may be attributed to the factA. nidulans var. dentatus is toxic in nature while S. maheswarium is egg parasitic. The fungiare able to degrade �-cyfluthrin to the acid and aldehydic moiety, which is a hydrolysisprocess and may be attributed to the presence of esterase enzyme present in the fungi. Thisstudy does not determine the enzyme type in the fungi responsible for the cleavage of theester linkage. The toxic fungus is able to degrade �-cyfluthrin at a relatively faster rate ascompared with the egg-parasitic fungus. In this study the enantiomers of �-cyfluthrin were

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not separately estimated and the selectivity of the fungus towards the enantioselectivedissipation process could not be ascertained, as reported by Lui et al. [20] in thedegradation observed during incubation of sediments under laboratory conditions ofbifenthrin and cis-permethrin. Similar results were observed when endosulfan was alsoeliminated from cultures of Aspergillius terreus and Cladosporium oxysporum [21].

The half life of �-cyfluthrin in PDA medium alone was recorded as 30 days, while inpresence of fungus A. nidulans var. dentatus and S. maheswarium was 11 and 19 days,respectively, showing that faster dissipation was observed in toxic fungus, A. nidulans var.dentatus as compared with the egg parasitic fungus, S. maheswarium. This is the first reportof the use of fungi isolated from nematode infested field, to eliminate �-cyfluthrin molecule.

The results show that the presence of fungus enabled elimination of �-cyfluthrincompared with control. Though the ability of fungi to eliminate the pesticide was proved,other strains need to be screened for the process to be effectively used in remediation ofcontaminated sites.

Acknowledgments

The authors thank Dr B. S. Parmar, Director Research, IARI and Dr G. Kulshrestha,Head Division of Agricultural Chemicals for providing the facilities for work. ContributionNo. 872, Divisions of Agricultural Chemicals, IARI, New Delhi.

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Table I. Degradation of �-cyfluthrin with nematophagous fungi A. nidulans var. dentatus and S. maheswarium.

Sampling daysMediumþ

�-cyfluthrin

Mediumþ

�-cyfluthrinþA. nidulansvar. dentatus

Mediumþ �-cyfluthrinþS. maheswarium

0 19.64� .02 19.70� 0.08 19.75� 0.033 18.32�0.03 (6.72) 16.42� 0.07 (16.64) 17.19� 0.06 (12.96)5 17.37�0.02 (11.55) 13.15� 0.03 (33.24) 15.58� 0.04 (21.14)7 16.71�0.03 (14.9) 12.12� 0.03 (38.47) 14.07� 0.02 (28.75)

10 15.86�0.04 (19.24) 10.11� 0.03 (48.68) 13.13� 0.02 (33.51)15 15.21�0.02 (22.55) 8.52� 0.02 (56.75) 11.24� 0.04 (43.08)20 14.93�0.03 (23.98) 5.36� 0.06 (72.79) 9.34� 0.03 (52.70)

Each value is a mean of three replicates, figure in parentheses is % dissipation, ND<0.01mg kg�1.

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