Chemosphere 84 (2011) 1416–1421

Contents lists available at ScienceDirect

Chemosphere

journal homepage: www.elsevier .com/locate /chemosphere

Residual behaviour and risk assessment of flubendiamide on Chickpea(Cicer arietinum L.)

Gurmail Singh, S.K. Sahoo ⇑, Reenu Takkar, R.S. Battu, B. Singh, G.S. ChahilPesticide Residue Analysis Laboratory, Department of Entomology, Punjab Agricultural University, Ludhiana, Punjab 141 004, India

a r t i c l e i n f o

Article history:Received 2 November 2010Received in revised form 11 April 2011Accepted 21 April 2011Available online 18 May 2011

Keywords:FlubendiamideDesiodo flubendiamideChickpeaResiduesRisk assessment

0045-6535/$ - see front matter � 2011 Elsevier Ltd. Adoi:10.1016/j.chemosphere.2011.04.065

⇑ Corresponding author.E-mail address: sksahoo_2006@rediffmail.com (S.K

a b s t r a c t

The study was undertaken to determine the disappearance trends of flubendiamide residues on chickpeaunder field conditions and thereby, ensure consumer safety. Average initial deposits of flubendiamide onchickpea pods were found to be 0.68 and 1.17 mg kg�1, respectively, following three applications of flu-bendiamide 480SC @ 48 and 96 g a.i. ha�1 at 7 d intervals. Half-life of flubendiamide on chickpea podswas observed to be 1.39 and 1.44 d, respectively, at single and double dosages whereas with respect tochickpea leaves, these values were found to be 0.77 and 0.86 d. Desiodo flubendiamide was not detectedat 0.05 mg kg�1 level on chickpea samples collected at different intervals. Theoretical maximum residuecontribution (TMRC) for flubendiamide was calculated and found to be well below the maximum permis-sible intake (MPI) on chickpea pods and leaves at 0-day (1 h after spraying) for the both dosages. Thus,the application of flubendiamide at the recommended dose on chickpea presents no human health risksand is safe to the consumers.

� 2011 Elsevier Ltd. All rights reserved.

1. Introduction

Flubendiamide, N2-(1,1-dimethyl-2-methyl sulfonyl ethyl)-3-iodo-N1-[2-methyl-4-{1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyl} phenyl] 1,2–benzene dicarboxamide, is a novel class of insecticidehaving a unique chemical structure. It belongs to phthalic acid dia-mide (Diaz de Toranzo and Brieux, 1967) insecticide developed byBayer Crop Science, Germany in collaboration with Nihon NohyakuCo. Ltd., Tokyo, Japan. The public introduction of flubendiamide wasin July 2005 (Nishimatsu et al., 2005) and the first registration wasobtained in Philippines in 2006, followed by Japan, Pakistan, Chile,India and Thailand in 2007. The uniqueness of the structure resultsfrom three parts with novel constituents: a heptafluoroisopropylgroup in the anilide moiety, a sulfonylalkyl group in the aliphaticamide moiety, and an iodine atom at the 3-position of the phthalicacid moiety. Flubendiamide has larvicidal activity as a stomach poi-son and is an oral intoxicant, fast acting (rapid cessation of feeding),long lasting (rain fast) and has limited plant penetration and system-icity. It has a novel biochemical action as it affects calcium ion bal-ance irrespective of sodium or potassium ion balance (Hall et al.,1995), which causes contraction of insect skeletal muscle (Usher-wood, 1962). Flubendiamide is mainly effective for controlling lepi-dopteran pests including resistant strain in pulses, rice, cotton, corn,grapes, other fruits and vegetables (Pessah, 1989; Tohnishi et al.,2005). Shane (2006) reported that flubendiamide is an excellent fit

ll rights reserved.

. Sahoo).

in the integrated pest management (IPM) programme and insecti-cide resistance management (IRM) programs in a variety of crops.The residues of flubendiamide have been estimated on crops suchas rice (Gopal and Mishra, 2008), chilli (Sahoo et al., 2009), tomato(Kooner et al., 2010) and cabbage (Mohapatra et al., 2010). However,no information is available on persistence of flubendiamide onchickpea. Chickpea (Cicer arietinum L.) is an important legume crop.It is major dietary protein source in South Asia, Middle East andNorth Africa (Berger et al., 2003). It is also important export cropfrom countries, where it is not a traditional food (e.g. Australia andCanada) (Loss et al., 1998). India is the largest chickpea produceras well as consumer in the world. India grows chickpea on about6.67 million ha area producing 5.3 million tonnes (Anonymous,2010). Immature and mature chickpea seeds can be cooked and ea-ten cold in salads, made curries and ground into a flour, and areknown to be nutritious and fibre rich. Young chickpea leaves alsoare eaten as a cooked vegetable, green, and could be a useful sourceof dietary nutrients especially in malnourished populations (Ibrikciet al., 2003). Of the various factors responsible for the low chickpeayield in India, insect pests are the most important. The damagecaused by Helicoverpa armigera during flowering and pod formationis the most concern. Due to heavy infestation, a 21% decline in pro-duction has been reported by Kumar and Smithson (1980) and 10–60% decline by Vaishampayan and Veda (1980). Many conventionalpesticides are being used to manage these pests. H. armigera devel-oped many fold resistance to several insecticides (Tatagar et al.,2009). In order to overcome the losses caused due to pests, tacticsbased on the use of newer insecticide are used. Studies revealed thatFlubendiamide effectively manage H. armigera on different crops

G. Singh et al. / Chemosphere 84 (2011) 1416–1421 1417

(Lakhminarayana and Rajashri, 2006; Kumar and Shivaraju, 2009;Tatagar et al., 2009). The presence of pesticidal residues in food com-modities is of concern to human health due to toxic nature of thepesticides. Hence it is imperative to study persistence of pesticideson edible crops to ensure human safety. In this context, the presentstudy was carried out to investigate the residual behaviour and riskassessment of flubendiamide on chickpea leaves, pods and soil atdifferent time intervals.

2. Materials and methods

2.1. Chemicals and reagents

All the solvents used for the preparation of stock and workingstandard solutions or in the extraction procedures were obtainedfrom Merck (Darmstadt, Germany). Chloroform was of GR gradeand acetonitrile, methanol and water were of HPLC grade. Beforeuse these were redistilled and their suitability was ensured by run-ning reagent blanks along with actual analysis. Activated charcoal(LR grade), sodium chloride (ACS reagent grade P99.9%) and so-dium sulfate (AR grade) were obtained from sd fine chemicals(Mumbai, India).

2.2. Preparation of standard solution

The certified reference standards of flubendiamide (purity99.5%) along with its des-iodo metabolite (purity 99.2%) were pro-cured from M/s Bayer Crop Sciences Limited (Mumbai, India). Thestock solution of flubendiamide and its metabolite prepared at1000 lg mL�1 in acetonitrile of HPLC grade and was stored at�20 �C. Working standards were prepared by appropriate dilutionswith acetonitrile and stored at 4 �C.

2.3. Field trial

Field trial was conducted during November 2009–March 2010according to recommended agronomic practices at entomologicalresearch farm, Punjab Agricultural University, Ludhiana, India,using randomized block design (RBD). First application of flubendi-mide-480 SC @ 100 and 200 g ha�1 was made at pod initiationstage using Aspee Knapsack sprayer equipped with hollow conenozzle. Subsequently two more applications were made at 7 dintervals. Each treatment was replicated thrice and the size of eachplot was 100 m2. Untreated control plots were sprayed with water.

2.4. Sampling

Chickpea, pods and leaves samples were brought to laboratoryat 0 (1 h), 1, 3, 5, 7, 10, 15 and 20 d after the last application ofinsecticide. Soil samples were collected after 20 d of the last appli-cation. The chickpea pods and leaves were collected from each plotseparately, packed in plastic bags and brought to laboratory forprocessing. A total of 500 g chickpea pods and 100 g leave sampleswere collected from each plot. Samples were extracted and cleanedup immediately after sampling. The field soil was analyzed for itsphysio-chemical properties at department of Soil Science, PunjabAgricultural University, Ludhiana, Punjab. The characteristics offield soil were sand 78.0%, slit 10.2%, clay11.8%, organic carbon0.30%, EC 0.30 dsm�1 and pH 8.0. The minimum and maximumtemperature during residue studies was 14.4 and 40.8�C respec-tively, with a relative humidity ranged from 14–90%. There wasno rainfall during study period.

2.5. Extraction and clean up method

The extraction and clean up of chickpea pods, chickpea leavesand soil samples for estimation of flubendiamide and desiodo flu-bendiamide residue was carried out as per procedure reported byBattu et al. (2008). Chickpea pods were mixed in a waring blender(Blixer 6 V.V. by robot coupe, France) and a representative 50 gchopped and macerated chickpea pods were dipped overnight into100 mL acetonitrile in an erlenmeyer flask. Leaf samples were pre-pared similarly and 10 g representative sample was dipped over-night into 20 mL acetonitrile. The extracts were filtered into 1 Lseparatory funnel along with rinsings of acetonitrile. The filtratein the separatory funnel was diluted with 600 mL brine solutionand partitioned the contents three times into 100, 50 and 50 mLchloroform. The chloroform fractions were combined, dried overanhydrous sodium sulfate and treated with 500 mg activated char-coal powder for about 2–3 h at room temperature. The clear extractso obtained was filtered through Whatman filter paper No. 1, con-centrated to near dryness and again added about 20 mL HPLC gradeacetonitrile and concentrated using rotary vacuum evaporator at30 �C. The process was repeated to completely evaporate chloro-form and the final volume was reconstituted to about 5 mL usingHPLC grade acetonitrile. A representative 50 g soil sample was ta-ken for analysis and processed as per the method described abovewithout any charcoal cleanup.

2.6. Estimation of residues

Residues of flubendiamide and desiodo flubendiamide wereestimated in chickpea pods, leaves and soil samples using HPLC-Shimadzu fitted with Phenomenex Luna 5 l C18 100 A column(250 � 4.6 mm, 5.20 lm particle size, 95 Å pore diameter,430 m2 g�1 surface area, <55.0 ppm metal content, 19% total car-bon and 3.25 lmoles m�2 surface coverage) connected to PDAdetector (SPD-M20A). HPLC was equipped with LC-20AT pumpand CBM-20A system controller. For instrument control, dataacquisition and processing, LC Solution software was used. Ali-quots of 20 lL sample extract were injected into HPLC at 254 k(wavelength) and using acetonitrile: water (80:20, v/v) mixtureas mobile phase @ 0.5 mL min�1. Residues were estimated by com-parison of peak height/peak area of the standards with that of theunknown or spiked samples run under identical conditions. Underthese operating conditions the retention time of flubendiamideand its metabolite were found to be 10.609 and 9.302 min,respectively.

The residues of flubendiamide and desiodo flubendiamide wereconfirmed on HPTLC- CAMAG, Linomat 5 applicator, Camag Linom-at syringe (100 lL), UV lamp with cabinet; TLC scanner 3 (Camag,muttenz, Switzerland); percolated silica gel (60F254) TLC alumin-ium sheet (Merck, Germany). For instrument control, data acquisi-tion and processing WINCATS software was used. Bands of 8 mmlength and six tracks were applied on each precoated TLC plate(10 cm � 10 cm). Linomat 5 applicator was programmed so thatbands were applied at a distance of 10 mm from the bottom andat least 12 mm distance between tracks. Distance between tip ofthe syringe and TLC plate was fixed at 1 mm for the sharp applica-tion of the bands. Sample bands were applied on the TLC plate atthe delivery rate of 200 nL s�1 and nitrogen gas used for dryingthe spots. Loaded plates were viewed inside the cabinet underthe UV light (225 nm) to ensure proper application before develop-ment. Loaded TLC plates developed in Camag-Automatic develop-ment chamber up to 80 mm in a paper lined chamber presaturated with 20 mL of Methanol. The flubendiamide and desiodoflubendiamide of developed plates were quantified by absorbanceat single wavelength in CAMAG TLC scanner 3 with D2 lamp (wave-length 190–400 nm) using WINCATS software. Each band was

Fig. 2. Linearity curve of desiodo flubendiamide and flubendiamide on HPLC.

1418 G. Singh et al. / Chemosphere 84 (2011) 1416–1421

quantified in a single beam, single wavelength reflectance mode,and relative front (Rf) was taken into consideration for confirma-tion of residues.

2.7. Efficiency of analytical method

Chickpea pods, leaves and soil samples were spiked with flu-bendiamide and des-iodo metabolite at three concentration levels(0.5, 0.25 and 0.05 mg kg�1) and analyzed as per the methodologydescribed above to estimate the trueness of the method. Percentrecoveries of flubendiamide and des-iodo metabolite in chickpeapods, leaves and soil were found to be consistent and more than75% (Fig. 1). Quantification was accomplished by standard curve,prepared by diluting the stock solution. Good linearity wasachieved with a correlation coefficient of 0.999 for flubendiamideas well as its metabolite, desiodo flubendiamide (Fig. 2). The preci-sion of the method was determined by repeatability studies of themethod and expressed as RSD values (Relative standard deviation).The RSD for repeatability, ranged from 2.83–6.51% for flubendia-mide and 3.54–5.74% for desiodo flubendiamide for different spik-ing levels as shown in (Table 1). Half-scale deflection was obtainedfor 25 ng flubendiamide which could be easily identified from thebaseline. A total of 50 g of chickpea substrate was extracted,cleaned up and final volume made to 10 mL. An aliquot of 20 lL(equivalent to 100 mg sample) from final volume when injecteddid not produce any background interference. Thus, limit of quan-tification (LOQ) was found to be 0.05 mg kg�1 and limit of detec-tion (LOD) being 0.017 mg kg�1. In case of leaves, 10 g samplewas processed and final volume was made to 2 mL, 20 lL of extract

(a)

(c)

mA

U

mA

U

Time (m

(a) Standard {desiodo fluben (b) Untreated control (c) Spiked sample of chickp (d) Field treated sample of c

i ii

Fig. 1. (a) Standard {desiodo flubendiamide (i) + flubendiamide (ii)}, (b) untreated contr

(100 mg sample) when injected did not show any evidence of chro-matographic interference. The T½ of flubendiamide was calculatedusing the Hoskins (1961) formula. Residues were estimated bycomparison of peak height/peak area of the standards with thatof the unknown or spiked samples run under identical conditions.

3. Results and discussion

The selected method of analysis of flubendiamide and desiodoflubendiamide in chickpea leaves, pods and soil samples by HPLCis relatively simple. Recovery studies carried out as per the methoddescribed above showed that recovery of flubendiamide in chick-pea pod was in the range of 88.80–94.10% and that of desiodo

(b)

(d)

mA

Um

AU

inute)

diamide (i) + flubendiamide (ii)}

ea pod hickpea pod

ol, (c) spiked sample of chickpea pod, and (d) field treated sample of chickpea pod.

Table 1Recovery studies of flubendiamide and desiodo flubendiamide on chickpea pods,leaves and soil.

Substrates Level of fortification(mg kg�1)

Flubendiamide Desiodoflubendiamide

Recovery(%)

RSDa(%) Recovery(%)

RSD(%)

Chickpeapod

0.50 94.10 4.16 88.35 3.420.25 88.80 3.68 85.51 3.250.05 89.30 6.51 87.13 3.99

Chickpealeaves

0.50 82.20 5.05 78.10 5.210.25 81.33 4.21 79.31 4.170.05 80.45 6.34 76.62 3.54

Soil 0.50 90.89 2.87 88.75 4.280.25 92.39 5.07 88.70 4.250.05 90.07 4.58 89.26 5.74

a Relative standard deviation.

Fig. 3. Semi-logarithm graph showing dissipation kinetics of flubendiamide onchickpea pods. Regression equation y = �0.59x + 2.61 (single dose) andy = �0.49x + 2.72 (double dose).

Fig. 4. Semi-logarithm graph showing dissipation kinetics of flubendiamide onchickpea leaves. Regression equation y = �0.39x + 2.56 (single dose) andy = �0.35x + 2.68 (double dose).

G. Singh et al. / Chemosphere 84 (2011) 1416–1421 1419

flubendiamide was, 85.51–88.35% in the concentration ranges0.50–0.05 mg kg�1 (Table 1). At the 0.05 mg kg�1 fortification levelthe recovery of flubendiamide in chickpea pod was found to be89.30 ± 5.81% and of desiodo flubendiamide was 87.13 ± 3.48%. Atthe same spiking level in leaves, the per cent recovery of flubendia-mide and its metabolite was 80.45 ± 5.10 and 76.62 ± 2.71, respec-tively. In case of soil the per cent recovery was found to be90.07 ± 4.13 for flubendiamide and 89.26 ± 5.13 for desiodo fluben-diamide at the 0.05 mg kg�1 fortification level.

The data relating to residues of flubendiamide in chickpea pod,leaves and soil from the field experiment carried out during rabi2009 are reported in Table 2. Three application of flubendiamide480SC @ 48 g a.i. ha�1 resulted in the initial deposit of 0.68 mg kg�1

in green pods. The same formulation when applied in a similarmanner @ 96 g a.i. ha�1, the average initial deposit of flubendiamidedetected was 1.10 mg kg�1. More than 70% of flubendiamide resi-dues dissipated after 3 d of the last application at both the doses.Residues of flubendiamide dissipated below LOQ of 0.05 mg kg�1

in 5 and 7 d at recommended and double the recommended dosage,respectively (Fig. 3). In case of leaves, the average initial deposits offlubendiamide were found to be 1.29 and 1.97 mg kg�1 at the twodoses which showed residues 1.80–1.90 time higher than that inpods. One day after application, these residues dissipated to theextent of about 51.16% and 56.34% at recommended and doublethe recommended dose, respectively (Fig. 4). Half- life of flubendia-mide on chickpea leaves calculated as per Hoskins was observed tobe 0.77 and 0.86 d when applied at 48 and 96 g a.i. ha�1. Residues of

Table 2Residues of flubendiamide on chickpea pods, leaves and soil at different time intervals aft

Interval (d) Flubendiamide residue in mg kg�1 ± standard

Chickpea pods

aT1bT2

0 (1 h after spray) 0.68 ± 0.03c (0.00) 1.10 ± 0.061 0.36 ± 0.02 (47.05) 0.61 ± 0.033 0.14 ± 0.02 (79.41) 0.29 ± 0.025 dBDL 0.10 ± 0.027 BDL BDL10 BDL BDL15 BDL BDLHarvest time after 20 d BDL BDLSoil samples after 20 d BDL BDLe T½ (d) 1.39 1.44

a T1 flubendiamide @ 48 g a.i. ha�1.b T2 flubendiamide @ 96 g a.i. ha�1.c () percentage dissipation after spraying.d BDL below determination limit of 0.05 mg kg�1.e T½ half-life in days.

flubendiamide dissipated below LOQ of 0.05 mg kg�1 in 10 and 15 dat single and double dosage, respectively. Desiodo flubendiamidewas not detected at 0.05 mg kg�1 level in pod and leaf samplescollected at different time intervals. Mature pods and soil samplescollected at 20 d after the last spraying did not reveal the presenceof flubendiamide and its metabolite desiodo flubendiamide. Theresidues of flubendiamide on chickpea were confirmed by relativefront (Rf) of the sample with that of reference standards undersimilar conditions. The reference standard of flubendiamide showeda relative front (Rf) value of 0.72. The samples taken from thetreated plots also showed relative front (Rf) value of 0.72, whichconfirmed the presence of flubendiamide. The adsorption spectra

er the application of flubendiamide (480SC) @ 100 and 200 mL ha�1.

deviation

Chickpea leaves

T1 T2

(0.00) 1.29 ± 0.06 (0.00) 1.97 ± 0.12 (0.00)(44.54) 0.63 ± 0.02 (51.16) 0.86 ± 0.04 (56.34)(73.64) 0.28 ± 0.02 (79.52) 0.42 ± 0.03 (78.68)(90.90) 0.13 ± 0.01 (89.92) 0.22 ± 0.02 (88.83)

0.07 ± 0.01 (93.02) 0.11 ± 0.02 (94.41)BDL 0.06 ± 0.007 (96.95)BDL BDLBDL BDLBDL BDL0.77 0.86

Table 3Theoretical maximum residue contributions (TMRC) in chickpea pods and leaves.

Days Maximumresidues inchickpea pod(mg kg�1) in T1

TMRC(mg person�1 d�1)

Maximumresidues inchickpea pod(mg kg�1) in T2

TMRC(mg person�1 d�1)

Maximumresidues inchickpea leaves(mg kg�1) in T1

TMRC(mg person�1 d�1)

Maximumresidues inchickpea leaves(mg kg�1) in T2

TMRC(mg person�1 d�1)

0 0.72 0.18 1.16 0.27 1.35 0.11 2.08 0.171 0.39 0.10 0.64 0.16 0.66 0.05 0.91 0.073 0.16 0.04 0.32 0.08 0.30 0.02 0.45 0.045 BDL – 0.13 0.03 0.14 0.01 0.24 0.027 – – BDL – 0.08 0.006 0.12 0.0110 – – – – BDL – 0.07 0.00615 – – – – – – BDL –

BDL Below determination limit (<0.05 mg kg�1).T1 flubendiamide @ 48 g a.i. ha�1.T2 flubendiamide @ 96 g a.i. ha�1.

1420 G. Singh et al. / Chemosphere 84 (2011) 1416–1421

of flubendiamide from the treated samples as well as referencestandard also matched.

Sahoo et al. (2009) reported initial deposits of 1.06 and2.00 mg kg�1, respectively, when flubendiamide was applied at 60and 120 g a.i. ha�1 on chilli. Following three applications of combi-nation mixture (flubendiamide 24% + thiacloprid 24%) 480 SC (w/v) at 48 and 96 g a.i. ha�1, the residues of flubendiamide dissipatedbelow LOQ of 0.05 in 3 and 5 d, respectively (Kooner et al., 2010).The half-life was found to range from 0.33 to 1.00 d. Mohapatraet al. (2010) studied the dissipation behaviour of flubendiamide incabbage and reported initial residue deposit 0.33 and 0.49 mg kg�1

following two application of flubendiamide @ 24 and 48 g a.i. ha�1.So, the results of present study were comparable to the earlier stud-ies on dissipation behaviour of flubendiamide.

4. Risk assessment

Human health risk situation are a function of hazard and expo-sure to that hazard. If the hazard is small and fixed, then the riskwill be proportional to exposure, which can be reduced to lowand occasional (Bates, 2002). Theoretical maximum residues con-tribution (TMRC) were calculated and compared with maximumpermissible intake (MPI) to evaluate the risk to the consumer forthe flubendiamide on chickpea pods and leaves. The prescribedacceptable daily intake (ADI) of flubendiamide by AustralianPesticides and Veterinary Medicines Authority (2009) is0.01 mg kg�1 body weight d�1. Maximum permissible intake(MPI) was obtained by multiplying the ADI with the weight ofaverage Indian person (55 kg) (Mukherjee and Gopal, 2000). MPIwas calculated to be 550 lg person�1 d�1. Taking 250 g as pulseconsumption for an Indian balanced diet (Mukherjee et al., 2011)and maximum residues on chickpea pods, the TMRC values on 0-d are found to be 0.18 and 0.27 mg person�1 d�1, in case of recom-mended dose (48 g a.i. ha�1) and double dose (96 g a.i. ha�1),respectively (Table 3). Both the values are low as compared toMPI, hence the insecticide will not cause adverse effect after con-sumption of such chickpea pods. Based on data reflecting maxi-mum residues on chickpea leaves that may occur under worstcondition on recommended (48 g a.i. ha�1), the TMRC value on 0-day was 0.11 mg person�1 d�1. The TMRC has been calculated atconsidering recommended consumption of vegetable as 80 g in In-dian Context (Anonymous, 1999). The TMRC values are also, foundto be well below MPI even if double dose is considered. As the the-oretical maximum residue contributions on chickpea pods as wellas leaves are found to be less than the toxicological estimated MPIvalue of 550 lg person�1 d�1, the consumer health risks are mini-mal at recommended dose on chickpea.

5. Conclusions

Flubendiamide, a novel class of insecticide has many favorablecharacteristics including selective activity against a broad rangeof lepidopteron pest, a new mode of action, safety to pollinatorshaving favorable environment and ecofriendly. Half-life valuesfor flubendiamide, following three applications at recommendedand double the recommended dosages on chickpea pods, was ob-served to be 1.39 and 1.44 d, respectively, whereas in case of chick-pea leaves, these values were 0.77 and 0.86 d. Residue data showedthat theoretical maximum residues contribution for flubendiamidewere found to be well below than maximum permissible intake onchickpea pods and leaves at 0-day (1 h after spraying) for the boththe dosages. Therefore, application of flubendiamide at the recom-mended dose on chickpea is quite safe from crop protection andenvironmental contamination point of view.

References

Anonymous., 1999. Dietary guidelines for the Indians. Indian Council of MedicalResearch.

Anonymous, 2010. All india coordinated research project on chickpea. <http://www.iipr.res.in/aircrp_chickpea>.

Bates, R., 2002. Pesticide residues and risk assessment. Pestic Outlook. 13, 142–145.Battu, R.S., Singh, B., Kooner, R., Singh, B., 2008. Simple and efficient method for the

estimation of residue of flubendiamide and its metabolite des-iodoflubendiamide. J. Agric. Food Chem. 56, 2299–2304.

Berger, J., Abbo, S., Tunner, N.C., 2003. Plant genetic resources ecogeography ofannual wild Cicer species – the poor state of the world collection. Crop Sci. 43,1076–1090.

Diaz de Toranzo, E.G., Brieux, J.A., 1967. Synthesis of unsymmetric o-phthalic aciddiamides. J. Med. Chem. 10, 982–983.

Gopal, M., Mishra, E., 2008. Analytical method for the estimation of new insecticideflubendiamide and its safety evaluation for usage in rice crop. Bull. Environ.Contam. Toxicol. 81, 360–364.

Hall, L.M., Ren, D., Feng, G., Eberl, D.F., Dubald, M., Yang, M., Hannan, F., Kousky, C.T.,Zheng, W., 1995. Calcium channel as a new potential target for insecticides. ACSSymp. Series 59, 162–172.

Hoskins, W.M., 1961. Mathematical treatment of the rate of loss of pesticideresidue. FAO Plant Prot. Bull. 9, 163–168.

Ibrikci, H., Knewtson, S., Grusak, M.A., 2003. Chickpea leaves as a vegetable green forhumans: evaluation of mineral composition. J. Sci. Food Agric. 83 (9), 945–950.

Kooner, R., Sahoo, S.K., Singh, B., Battu, R.S., 2010. Dissipation kinetics offlubendiamide and thiacloprid on tomato (Lycopersicon esculentum Mill) andsoil. Qual. Assur. Safe. Crops Foods 2 (1), 36–40.

Kumar, C.T.A., Shivaraju, C., 2009. Evaluation of newer insecticide molecule againstpod borers of black gram. Karnataka J. Agric. Sci. 22 (3), 521–523.

Lakshminarayana, S., Rajashri, M., 2006. Flubendiamide 20% WG – a new moleculefor the management of American bollworm, Helicoverpa armigera on cotton.Pestology 30, 16–18.

Loss, S., Brandon, N., Siddique, K.H.M. (Eds.), 1998. The chickpea book – A technicalguide to chickpea production. Bulletin 1326. Agriculture Western Australia. 76pp.

Mohapatra, S., Ahuja, A.K., Deepa, M., Sharma, D., Jagadish, G.K., Rashmi, N., 2010.Persistence and dissipation of flubendiamide and des-iodo flubendiamide incabbage (Brassica oleracea Linn) and Soil. Bull. Environ. Contam. Toxicol. 85,352–356.

G. Singh et al. / Chemosphere 84 (2011) 1416–1421 1421

Mukherjee, I., Gopal, M., 2000. Environmental behaviour and translocation ofimidacloprid in eggplant, cabbage and mustard. Pest. Manag. Sci. 56, 932–936.

Mukherjee, I., Singh, R., Govil, J.N., 2011. Risk assessment of a synthetic pyrethroid,bifenthrin on pulses. Bull. Environ. Contam. Toxicol. 84, 294–300.

Nishimatsu, T., Hirooka, T., Kodama, H., Tohnishi, M., Seo, A., 2005. Flubendiamide –a new insecticide for controlling lepidopterous pests. In: Proceedings of theBCPC International Congress, Crop Science and Technology, vol. 2A-3, Glasgow,United Kingdom, pp. 57–64.

Pessah, I.N., 1989. Recent advances in the chemistry of insect control. In: Crombie, L.(Ed.), Special Publication, vol 79. Royal Society of Chemistry, Cambridge, pp.278–296.

Sahoo, S.K., Sharma, R.K., Battu, R.S., Singh, B., 2009. Dissipation kinetics offlubendiamide on chilli and soil. Bull. Environ. Contam. Toxicol. 84, 384–387.

Shane H., 2006 Flubendiamide: the next generation in lepidopteran pestmanagement. Paper presented at the Annual Meeting of the EntomologySociety of America (ESA) held at Research triangle Park, NC, 10–13 December,2006.

Tatagar, M.H., Mohankumar, H.D., Shivaprasad, M., Mesta, R.K., 2009. Karnataka. J.Agric. Sci. 22 (3), 579–581.

Tohnishi, M., Nakao, H., Furuya, T., Kodama, H., Tsubata, K., Fjioka, S., Kodama, H.,Hirooka, T., Nishimura, T., 2005. Flubendiamide, a novel insecticide highlyactive against Lepidopterous insect pests. J. Pestic. Sci. 30, 354–360.

Usherwood, P.N.R., 1962. The action of the alkaloid ryanodine on insect skeletalmuscle. Comp. Biochem. Physiol., 6181–6199.

Vaishampayan, S.M., Veda, O.P., 1980. Population dynamics of gram pod borer,Helicoverpa armigera (Hub) and its outbreak situation on gram, Cicer arietinumL. at Jabalpur. Indian J. Ent. 42, 453–459.