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Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes

  • Mahwash Mahar Gul and Khuram Shahzad Ahmad EMAIL logo
Published/Copyright: April 20, 2020
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Open Chemistry
From the journal Open Chemistry Volume 18 Issue 1

Abstract

Detoxification and management of environmental contaminants is an exigent issue of current times. Sulfonylurea herbicide, Bensulfuron-methyl was investigated for its degradation demeanour in soils, through biotic and abiotic modes (biodegradation and hydrolysis). Solid-liquid extraction of the herbicide was followed by GC-MS and UV-visible spectrophotometry analysis. The main metabolites observed were pyrimidinamine [149 m/z] and benzylsulfonamide [182 m/z]. The rate of biodegradation achieved by Aspergillus niger and Penicillium chrysogenum was 95% and 71%, respectively. The maximal decline in Bensulfuron-methyl concentration through hydrolysis was 48%. Furthermore, hydrolytic elimination was also evaluated based on time and pH. Both these parameters had a strong influence on the rate of transformation. Soils with lower pH exhibited an increased rate of degradation while a temperature of 27±2°C gave ideal conditions for herbicide decomposition. Percentage degradation and rate constant (k) followed first order reaction kinetics. Non-inoculated soils displayed less amounts of degradation. Furthermore, relative standard deviations were calculated for the residuals extracted in all soils. Analysis of variance (ANOVA) provided a p value < 0.05 for both strains with R2 closer to 1 signifying the significance of the results. Both fungal strains proved their potential for Bensulfuron-methyl remediation in soils.

Keywords: sulfonylurea; GC-MS; metabolites; hydrolysis; herbicide

1 Introduction

The cardinal function of pesticides is the elimination of pests, not only in the rural agricultural setups but in urban dwellings as well [1]. Their extensive application is being met with some serious implications regarding their persistence in environment as well as their toxicological effects on non-targeted species [2]. The boundless use of pesticides is raising formidable issues, as only < 5 % of these agrochemicals applied, actually reach their desired destination [3]. The remains of the applied pesticide are more commonly present in surface and ground waters. Due to their mobile nature, these pesticides contaminate diverse layers of soil and environment through leaching, volatilization or sorption. Consequentially, they can reach water bodies either directly by runoff from agricultural fields or indirectly through industrial wastes [4]. Pesticides, which promptly degrade naturally in environment, are non-persistent while those that do not degrade easily are persistent. The persistent agrochemicals are responsible for the detrimental effects on the environment due to their prolonged stay. They are also responsible for creating resistance in pests towards them [5]. The degradation of pesticides involves different routes, which results in the decontamination of the environmental system at varying rates. Expediting the rate of degradation causes faster detoxification of the environment in lesser time. Decontamination of soils and water bodies from these pesticides is thus crucial [6]. However, physicochemical modes of decontamination such as land filling, incineration or recycling are less productive and costly [7]. Hence, photo-degradation, biodegradation and hydrolysis are more dominant methods for pesticides removal. Among these, biodegradation is paramount for removal of toxic chemicals, as microbes are present in abundance in nature [8]. The survival of microorganisms is mostly dependent on the bioremediation phenomena, as they consume these chemicals as a source of nutrients. Soils and water bodies can be decontaminated either by naturally occurring microbes in the environment or by bio-augmentation of these environments with microbes [9]. This process is highly beneficial due to less damage to the ecosystem whilst being more economical and is used in several countries globally. Microbes are among the main degrading microbes of xenobiotics including pesticides. In the biodegradation phenomena, several enzymes and gene clusters are involved [10]. In recent advances, bacteria with engineered genes are used in the degradation of pesticides. Several fungal strains including, Aspergillus niger, Fusarium verticillioides, Fusarium oxysporum, Lentinula edodes, Penicillium brevicompactum and Lecanicillium saksenae, have been isolated and screened, which have been further utilized for removal of toxic substances including endosulfan, terbuthylazine, difenoconazole, and pendimethalin and several sulfonylurea herbicides. To boost up the degradation process a mixture of fungal strains in the form of a consortium is also utilized [11].

Sulfonylurea herbicides display a positive response towards microbial degradation. One such example is the degradation of nicosulfuron by Pseudomonas flourescens, isolated from agricultural soils. 77.5% Nicosulfuron was degraded by the bacterial strain [12]. Berger and Wolfe were successful in degrading 12 sulfonylurea herbicides. According to their results, microbial degradation was dominant at neutral pH while hydrolysis occurred at low pH values [13]. Furthermore, Pergal et al. also studied nicrosulfuron and thiensulfuron methyl degradation recently through chlorine dioxide in water [14]. An impressive degradation was achieved for metsulfuron methyl by enzymatic action. A degradation rate of 93% was achieved after just 10 min [15]. A mixture of sulfonyurea herbicides was degraded by B. megaterium, isolated from an agricultural soil [16].

Bensulfuron-methyl (BSM), a sulfonylurea herbicide with chemical name, Methyl α-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluate, is a white to light yellow, fine crystalline powder. Although applied in low quantities, BSM has high application rates [17]. It targets on weeds like Cyperaceae, Butomaceae and Alismataceae growing in the rice fields [18,19]. A weed specie Sagittariatrifolia L has been found to be resistant to BSM due to mutation in acetolactate synthase gene [18]. It was found to be accumulated in brown rice and rice straw because of its persistent nature [20]. At neutral pH, the half-life of BSM is approximately 143 days [21]. It has been found to be degraded by several microbes including Ochrabacterium sp., Brevibacterium, Bacillus megaterium, Methylopila sp. among others [22,23].

A massive use of pesticides is observed in the agricultural country of Pakistan especially herbicide Bensulfuron-methyl, because of the abundance of crops grown such as wheat and rice. In order to understand BSM mitigation in contaminated soils, it is necessary to study its degradation behaviour in environment. The current research investigates the degradation trend of BSM including bioremediation and hydrolysis in soils with distinct physicochemical properties utilizing two fungi: Aspergillus niger and Penicillium chrysogenum. Metabolites obtained from BSM degradation can be utilized in prediction of the toxicological fate of this herbicide in soil.

2 Experimental

2.1 Reagents

Bensulfuron-methyl (ACCU, USA), anhydrous Na2SO4 (Sigma-Aldrich, Germany) and dichloromethane (DCM) (RCI-Labscan, Thailand).

2.2 Fungal strains

Two fungal strains; Aspergillus niger and Penicillium chrysogenum, were contributed by the Mycotoxicology Lab, Environmental Sciences Department, Fatima Jinnah Women University, Rawalpindi, Pakistan. Fungi were cultured in petri plates comprising PDA inside a laminar flow hood and incubated at 29°C for 5 days.

2.3 Soil samples

Biodegradation experiments were conducted on four soils from various locales of Pakistan encompassing, Bahawalpur (Soil 1), Swabi (Soil 2), Mianwali (Soil 3) and Pasni (Soil 4) from a depth of 0-20 cm. The physical and chemical analysis of soil samples was done by Soil and water testing laboratory, Pakistan. Soil tests underwent further processing [24]. Results of biodegradation were analysed by gas chromatography mass spectrometry (GCMS-QP5050 (SCHIMADZU)) and UV-Vis spectrophotometer (BMS-1602, Biotechnology Medical Services K. Group, U.S.A). A pesticide stock solution of 10 ppm concentration was prepared for biodegradation experiments while a dilution of 1 ppm for hydrolysis experiments was prepared.

2.4 Soil Mycoremediation experiments

Approximately 5 g soil, 2 ml BSM initial solution and 10 ml spore suspension of both A. niger (6.3 x105 spores ml-1) and P. chrysogenum (6.0 x105 spores ml-1) were added in individual glass vials. Control samples were prepared devoid of fungal suspension with only containing pesticide and soil solution. Moisture content was maintained at 70-80% of WHC. Capped tubes were vortexed at 20(x100) rpm to ensure a homogenous mixture. The vials were kept in incubator (27±2°C) for 21 days. Sampling was done from each vial at multiple intervals (7, 14 and 21 days). Experimentation was performed in duplicates [25]. Fungal growth was observed and calculated by using a haemocytometer under a microscope on the days of extraction.

2.5 BSM hydrolysis

Hydrolysis experiments for BSM degradation in both soil and water were performed following the technique used by Sarmah et al. [26].

2.6 Pesticide extraction

Extraction was performed using 5 ml DCM twice, followed by evaporation. Followed by evaporation, 1.5 ml extractant was stored in eppendorf tube. These tubes were put in refrigerator at -4°C until further analysis [27].

2.7 Chromatographic investigation

The samples were examined by GC–MS (QP5050A, Shimadzu, Japan) system equipped with a DB-5MS fused quartz capillary column (30 mm × 0.25 mm × 0.25 μm). The temperature program was set as following: initial temperature 150°C held for 2 min up to 250°C at 10 °C/ min (maintained 10 min). Injector temperatures was maintained at 280°C. Helium was used as carrier gas at a flow rate of 1.2mL/ min.

2.8 UV-Visible spectrophotometer analysis

BSM hydrolysis rate was analysed by UV-Visible spectrophotometer (UV-BMS 1602). Full scan at wavelengths of 190-250 nm was run for each sample. Bensulfuron-methyl peak was attained at 200 λmax (nm).

2.9 Degradation percentage and kinetics

The rate of BSM degradation was determined after GC-MS analysis. Means of the duplicate values of samples were utilized. Percentage degradation of BSM was calculated by the following formula (Equation 1):

(1)Bt=Db−DaDb×100

where, Bt is the degradation of BSM in percentage at a precise time t, Da is the residual pesticide left in the sample after time t and Db is the quantity of pesticide in control sample [28]. The pseudo-first order rate constant for the degradation of BSM was determined by the integrated arrangement of the first order reaction kinetics (Equation 2).

(2)lnCt=−kt+lnC∘

where, Ct is the pesticide concentration at time t, C° is the pesticide concentration at the start and k is the degradation rate constant.

The rate constant, k was obtained by the following equation (Equation 3).

(3)Rate(k)=−Δ[c]Δt

Half-life was determined by Equation 4,

(4)t12=0.693k

The data was subjected to statistical analysis for further confirmation of results.

Ethical approval: The conducted research is not related to either human or animal use.

3 Results and discussion

3.1 Soil properties

Physical and chemical properties of soil were studied and analysed from four regions of Pakistan. These locations displayed variable physical and chemical properties (Table 1). The effects of diverse soil characteristics on pesticide biodegradation and hydrolysis were assessed. Soils in the current experiment displayed a neutral to alkaline trend with only one soil exhibiting slight acidic pH. Soils of this region have been reported previously to be generally alkaline in nature. Basic pH of soil facilitates the accruing of a higher concentration of salt, which affects soil matrix causing capriciousness and has a detrimental impact on it. According to the physicochemical characterisation, soil 3 possessed the lowest pH (6.6) while the highest pH value was found in soil 4 (8.6). An opposite trend for organic matter (OM) was observed in these soils, with soil 3 showing maximum organic matter (3.3%) and soil 4 displaying the least organic matter content (1.8%). This could be one of the reasons for soil 3 to be more fertile, producing greater agricultural yield while soil 4 being less fertile showing minimal agricultural yield. Soils with pH in alkaline range hinder the uptake of water, which consequentially elevates the sodium content and adversely affects the underlying biochemical processes required for the sustainability of organic content. The sand content in soil 4 was found highest among all soil samples (61%) while the clay content was lowest (6.3%). Textural aspects are imperative and one of the decisive factors for governing the rate of degradation of pesticide. Based on the textural analysis, Bahawalpur and Swabi soil was found to be sandy, Mianwali soil was found to be clay in nature and Pasni soil was sandy loam. Various types of textural classes display the potential of soils variability towards degradation. Soils were also tested for their electrical conductivity. A higher EC value depicts greater salinity of soil, which impedes the water uptake and pose the peril of soil’s salinity hazard.

Table 1

Physical and chemical characteristics of soil samples.

SoilpHOM[1]

(%)		TN[1]

(%)		TOC[1]

(%)		WHC[1]

(ml l-1)		CEC[1]

(Meq100g-1)		EC[1]

(μScm-1)		Pb

(ppm)		Cd

(ppm)		Ni

(ppm)		Cu

(ppm)		Zn

(ppm)
17.42.70.131.5667.82403.130.680.770.170.20
27.32.30.361.3607.51200.720.060.68N.D0.09
36.63.30.311.1487.884.03.311.160.73N.D0.08
48.61.80.091.0527.02323.470.150.430.040.08

3.2 Biodegradation experiments

Fungal strains: Aspergillus niger and Penicillium chrysogenum were added in the soil samples and spiked with BSM for bioremediation experiments. BSM was monitored as to whether or not it acts as a nutrition source for the fungi. A constant temperature (27±2°C) was provided to the samples for optimal fungal growth. No effect of temperature change on fungal cells was taken into account since a constant temperature was maintained at a constant during the experiment.

After 21 days, soil 3 displayed highest percentage of BSM degradation. Soil 3 exhibited 95% of dissipation by Aspergillus niger while the least reduction was seen in soil 4 (57%). Similarly, the degradation rate by Penicillium chrysogenum was highest in soil 3 (71%) and lowest in soil 4 (50%). These varying degradation trends were observed due to the relative percentages of OM present in the soil samples. Degradation rate of BSM was observed to be influenced by soil physicochemical properties. The presence of higher organic matter in soil 3 rendered it to be more favourable for degradation. OM provided better conditions for the fungal strains to strive in soil and convert BSM to its metabolites through the action of its enzymes, such as hydrolases and peroxidases [29,30]. Another factor playing a crucial role in the high rate of degradation in soil 3 was its low pH value as compared with rest of the soil samples. As a consequence of low pH, it exhibited a greater degree of degradation. It was observed that pH and the rate of degradation are inversely proportional. The lowest rate of degradation observed in soil 4 can be attributed to the least amount of OM (1.8%) as well as its highest pH (8.6). Soil 4 displayed a considerably higher amount of heavy metals present in it as compared to the other soils. Microbes including fungi have been found to degrade other molecules as well. The presence of heavy metals affects degradation rate of BSM as it may result in reduced or unavailability for degradation. In case of soil 4, the least degradation can be attributed to lowest amount of OM, highest pH and the presence of heavy metals (Table 2; Table 3). The increase in fungal cells was observed throughout the experiment and calculated by a haemocytometer. The fungal cells of A. niger and P. chrysogenum increased from 6.3x105 and 6x105 viable fungal spores mL-1 to 12.8x105 and 11.4 x105 viable fungal spores mL-1 respectively.

Table 2

Biodegradation of Bensulfuron-methyl by Aspergillus niger.

SoilPercentage degradation (Dt) (%)ln[C] of pesticides concentrationSlope (k) (1/s)Half-life T1/2 (Days)
Day 7Day 14Day 21Day 7Day 14Day 21
1332870.550.23-4.66-0.450.52
2113640.33-4.92-5.94-1.751.54
3274695-0.03-4.03-5.94-1.330.39
42021571.720.35-4.49-0.106.93
Table 3

Biodegradation of Bensulfuron-methyl by Penicillium chrysogenum.

SoilPercentage degradation (Dt) (%)ln[C] of pesticides concentrationSlope (k) (1/s)Half-life T1/2 (Days)
Day 7Day 14Day 21Day 7Day 14Day 21
12545680.68-2.63-5.52-0.720.9
2263657-2.08-4.24-4.93-0.322.1
3113771-3.16-3.97-4.69-1.100.6
4213850-3.86-4.02-4.32-0.272.5

The plots of percentage degradation (Dt) versus time gave an exponential curve indicating that the decomposition of Bensulfuron-methyl followed first order reaction kinetics (Figure 1). In table 2 and 3, the percentage degradation (Dt) discernibly showed very less degradation at day 7. After that, an increase in degradation was detected on days 14 and 21. The low rate of degradation on the 7th day can be due to the lag phase of the microbes in the medium. The fungal spores take some time to be acquainted with the new environment provided, causing a delay in the decomposition process of BSM. The first order reaction kinetics equation was followed to determine the rate constant of degradation (k) for all the soil samples.

Figure 1 Map exhibiting the soil locations for transformative studies on chemical BSM.
Figure 1

Map exhibiting the soil locations for transformative studies on chemical BSM.

The range of biodegradation trends obtained was attributable to different pH values of the soil samples. Soils with higher pH values showed less rate of degradation than the soils with a lower pH value. This is because a higher mobility of BSM is observed in soils with a higher pH value, consequentially making the pesticide unavailable for the fungi to consume; hence, a faster rate of BSM reduction was observed in acidic soils. The BSM molecule tends to be more dissociated in soils with higher pH thus becoming polar. This provides less probability for the molecule to be available for decomposition by fungal cells as its mobility increases [31]. In Figure 1(a) and 1(b), an exponential increase in fungal spore count can be seen along with a declining trend of pesticide, Bensulfuron-methyl, in all soil samples. This confirms that the fungal spores are consuming the pesticides as their nutrition source and thus reproducing. In Figure 1(c) and 1(d), the declining trend lines of control samples can be seen giving a lesser slope. It can be visualized in the plots that the decline of BSM in control samples (containing only pesticide in soils with no fungal cells) is very less as compared to the inoculated samples. This slight decrease is due to either chemical hydrolysis or pesticide adsorption.

Analysis by GC-MS required no additional clean-up after extraction of BSM from the samples. Bensulfuron-methyl was detected in the standard solution at Rt 12.7 min in the total ion chromatogram. Several metabolites were formed as a result of BSM decomposition by fungi. The results of GC-MS were analysed and compared with the online NIST library. This study of the transformation products of BSM provided the information about how BSM changed structurally through the action of fungal strains in the soil samples (Figure 2). According to SCAN mode, the major transformation products were obtained at m/z 149, 182, 411 and 412 [32] (Table 4). The SCAN mode highly increased the sensitivity throughout the chromatographic run [33]. The profuse daughter ion for BSM was observed to have the highest quantitative sensitivity. The SCAN mode provided affirmatory evidence about the transition products of BSM. The SCAN GC-MS has been used previously for several environmental and medical analysis. The weakest metabolite observed at the m/z chromatogram could be used to determine the lowest level of detection of BSM [34]. The sulfonylurea bridge of BSM was broken down to form pyrimidinamine [149 m/z] and benzylsulfonamide [182 m/z] [35]. BSM molecules can interact with fungal cells in a variety of processes including bioaccumulation, biosorption or biotransformation (Figure 3).

Figure 2 Biodegradation of BSM in soil samples (a) Percentage decrease in BSM concentration by A. niger. (b) Percentage decrease in BSM concentration by Penicillium chrysogenum. (c) Linear plot of ln[Ct/Co] for BSM by A. niger. (d) Linear plot of ln[Ct/Co] for BSM by Penicillium chrysogenum.
Figure 2

Biodegradation of BSM in soil samples (a) Percentage decrease in BSM concentration by A. niger. (b) Percentage decrease in BSM concentration by Penicillium chrysogenum. (c) Linear plot of ln[Ct/Co] for BSM by A. niger. (d) Linear plot of ln[Ct/Co] for BSM by Penicillium chrysogenum.

Figure 3 GC-MS chromatogram of Bensulfuron-methyl main peak at 12.7 Rt. Inset: Mass table of BSM metabolites. An m/z spectrum with main degradation products of BSM at 149 and 182 m/z.
Figure 3

GC-MS chromatogram of Bensulfuron-methyl main peak at 12.7 Rt. Inset: Mass table of BSM metabolites. An m/z spectrum with main degradation products of BSM at 149 and 182 m/z.

Table 4

Ions selected for SCAN with their retention times and relative abundances for BSM molecular weight 410.

IonsRelative abundanceRetention times m/z
Base peak [MH]+100149
[M+H]42.9411
[M+2H]43.2412

Aspergillus niger is an active degrading fungal specie, responsible for dissipation of multiple herbicides. Sharma et al. reported the biotransformation of pesticide chlorimuron-ethyl by A. niger by two routes, sulfonylurea bond cleavage and scission of sulfonylamide link [36]. Other herbicides commonly degraded by A. niger include, nicosulfuron, metsulfuron-methyl, chlorsulfuron [37, 38, 39]. Chlorimuron-ethyl, a sulfonylurea herbicide, displayed 81% degradation by Pseudomonas sp. [40]. In another investigation, three sulfonylurea herbicides, rimsulfuron, triasulfuron and primsulfuron were degraded in microbially active soils, which displayed shorter half-lives than in sterile soils [41].

3.3 Statistical evaluation

The means of residual quantities acquired were calculated. The standard deviations and relative standard deviations (R.S.D.) were evaluated (Table 5). R.S.D. between different soils was high at all extractions because of the distinct differences among the recovery rate of each soil due to the varying physical and chemical characteristics. Furthermore, ANOVA statistical tool was applied on the degradation percentage (Dt) for both the strains indicating p value to be < 0.05 in both cases, thus proving the significance of the degradation results. The R2 values for all soils for both strains were close to 1 indicating the significance of results (Table 6).

Table 5

Mean recovery concentration and standard deviation of residuals.

DaysMean recovery

concentration (mg)		Sample S.D.[1]R.S.D.%[2]
72.4002.15089
140.6500.750114
210.0060.00459
Table 6

Linear regression analysis and analysis of variance on Bensulfuron-methyl biodegradation by fungi.

Fungal strainsSoil

samples		P-valueLinear regression

equation		R2
Aspergillus nigerSoil 10.03y = 0.30x + 270.9
Soil 20.04y = 0.70x + 300.9
Soil 30.02y = 0.50x + 100.8
Soil 40.05y = 0.25x + 440.9
Penicillium chrysogenumSoil 10.01y = 0.93x + 130.9
Soil 20.06y = 0.28x + 250.8
Soil 30.05y = 0.50x +190.9
Soil 40.004y = 0.22x + 540.9

3.4 Hydrolysis experiments

3.4.1 Effect of pH

The process of degradation is not only a result of microbial action but also a consequence of chemical degradation. During hydrolysis, the decrease in pH is the main factor governing the rate of decomposition of BSM [42]. When fungal cells initially attack the pesticide, it lowers down the pH. Hence, further losses occur through the hydrolysis of BSM in media [43].

Chemical hydrolysis experiments were also performed on soil and corresponding water samples. pH of the water samples was adjusted according to the corresponding soils. Highest degradation rate was seen in soil 3 (48%). Although the reduction is quite less than fungal degradation (95%), it is still a decent degradation percentage through hydrolysis. During the process of hydrolysis, the carbonyl carbon bridge is cleaved by water, which releases CO2 creating sulphonamide and heterocyclic amine. The amine further converts to metabolites [44]. The degradation through hydrolysis can be observed in Figure 4. The rate of hydrolysis in water samples did not deviate much from that observed in soil samples. This was because the pH of water samples was attuned with that of the corresponding soils. The highest hydrolysis rate observed in soil 3 was also because of the lowest pH [45]. Even in case of fungal degradation, the increased and rapid decomposition was due to the assisted hydrolysis of the pesticide.

Figure 4 Possible interactions of pesticide with a fungal cell in soil.
Figure 4

Possible interactions of pesticide with a fungal cell in soil.

3.4.2 Effect of temperature

Effect of temperature change was also assessed in order to observe the change in the rate of degradation. All the vials were initially placed at a reduced temperature (4°C) for two days. After two days, UV analysis was done following liquid-liquid extraction. No change in the UV absorbance was observed indicating that same amount of Bensulfuron-methyl was still present in all the samples [46]. The temperature was then increased to 15°C. The samples were kept at this temperature for another two days followed by UV analysis. A slight decrease in the absorbance peak was detected by the UV-vis spectrophotometer. This depicted that the herbicide decomposed to some extent through chemical break down. The temperature was again increased to an optimum 27°C for two days. UV analysis exhibited a sharp decline in the concentration of BSM (Figure 5). Briefly, it can be stated from the obtained results that lower temperatures did not encourage BSM degradation while elevated temperature accelerated its decomposition by breaking down the sulfonylurea bridge in its structure [47]. Increased temperature at an optimum range of 27°C was ideal for BSM hydrolysis.

Figure 5 Linear plots of log of concentration of Bensulfuron-methyl hydrolysis with time (days). (a) Hydrolysis in soil samples. (b) Hydrolysis in water with pH corresponding to that of soil samples.
Figure 5

Linear plots of log of concentration of Bensulfuron-methyl hydrolysis with time (days). (a) Hydrolysis in soil samples. (b) Hydrolysis in water with pH corresponding to that of soil samples.

Generally, sulfonylurea herbicides display varying responses towards hydrolysis mechanism. It is mostly dependent upon the chemical structure of the herbicide and temperature/pH of the environment. Dinelli et al. also displayed a varying response of primsulfuron, rimsulfuron and thiensulfuron towards hydrolytic degradation. Some herbicides displayed rapid degradation while some exhibited extended half-lives of 49-399 days [48]. The dissipation rates of all the herbicides depended upon range of temperature and pH of the medium.

Figure 6 Temperature effect on hydrolysis rate in soil sample 3.
Figure 6

Temperature effect on hydrolysis rate in soil sample 3.

4 Conclusion

Bensulfuron-methyl was studied for its degradation behaviour in four soils through the use of common soil borne fungal strains. Following the solid-liquid extraction of Bensulfuron-methyl in four soil samples, it was observed that pH factor and temperature are highly imperative for the rate of degradation. Fungal strains: Aspergillus niger and Penicllium chrysogenum showed high rates of BSM degradation. Acidic soils showed more rapid degradation than alkaline soils. Similarly, an optimal temperature of 27°C was found ideal for degradation. Although these studies were carried out in laboratory under artificial conditions, they will be crucial to predict the effect of degradation and the formation of the transformation products in actual field conditions. Fungal degradation and chemical hydrolysis are dominant modes of decomposition of Bensulfuron-methyl in soils and liquid media. However, further investigation is needed to find the mechanisms of fungal enzymes and its mode of action to assess the degradation trends for various chemicals. The results provide a critical insight into bioremediation of BSM contaminated soils.

  1. Conflict of interest: Authors declare no conflict of interest.

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Received: 2019-07-09
Accepted: 2019-12-15
Published Online: 2020-04-20

© 2020 Mahwash Mahar Gul, Khuram Shahzad Ahmad, published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2020-0030
Keywords for this article
sulfonylurea; GC-MS; metabolites; hydrolysis; herbicide
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Electrochemical antioxidant screening and evaluation based on guanine and chitosan immobilized MoS2 nanosheet modified glassy carbon electrode (guanine/CS/MoS2/GCE)
  3. Kinetic models of the extraction of vanillic acid from pumpkin seeds
  4. On the maximum ABC index of bipartite graphs without pendent vertices
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  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
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  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
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  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
  19. Rapid identification of direct-acting pancreatic protectants from Cyclocarya paliurus leaves tea by the method of serum pharmacochemistry combined with target cell extraction
  20. Immobilization of Pseudomonas aeruginosa static biomass on eggshell powder for on-line preconcentration and determination of Cr (VI)
  21. Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes
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  25. Synthesis and characterization of calcium carbonate whisker from yellow phosphorus slag
  26. Study on the interaction between catechin and cholesterol by the density functional theory
  27. Analysis of some pharmaceuticals in the presence of their synthetic impurities by applying hybrid micelle liquid chromatography
  28. Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: the protective effect on periodontitis via reducing the release of IL-1β and TNF-α
  29. Incorporation of silver stearate nanoparticles in methacrylate polymeric monoliths for hemeprotein isolation
  30. Development of ultrasound-assisted dispersive solid-phase microextraction based on mesoporous carbon coated with silica@iron oxide nanocomposite for preconcentration of Te and Tl in natural water systems
  31. N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells
  32. Determination of the content of selected trace elements in Polish commercial fruit juices and health risk assessment
  33. Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study
  34. Keratin 17 is induced in prurigo nodularis lesions
  35. Anticancer, antioxidant, and acute toxicity studies of a Saudi polyherbal formulation, PHF5
  36. LaCoO3 perovskite-type catalysts in syngas conversion
  37. Comparative studies of two vegetal extracts from Stokesia laevis and Geranium pratense: polyphenol profile, cytotoxic effect and antiproliferative activity
  38. Fragmentation pattern of certain isatin–indole antiproliferative conjugates with application to identify their in vitro metabolic profiles in rat liver microsomes by liquid chromatography tandem mass spectrometry
  39. Investigation of polyphenol profile, antioxidant activity and hepatoprotective potential of Aconogonon alpinum (All.) Schur roots
  40. Lead discovery of a guanidinyl tryptophan derivative on amyloid cascade inhibition
  41. Physicochemical evaluation of the fruit pulp of Opuntia spp growing in the Mediterranean area under hard climate conditions
  42. Electronic structural properties of amino/hydroxyl functionalized imidazolium-based bromide ionic liquids
  43. New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties
  44. Treatment of adhesions after Achilles tendon injury using focused ultrasound with targeted bFGF plasmid-loaded cationic microbubbles
  45. Synthesis of orotic acid derivatives and their effects on stem cell proliferation
  46. Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis
  47. Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives
  48. Adsorption kinetic characteristics of molybdenum in yellow-brown soil in response to pH and phosphate
  49. Enhancement of thermal properties of bio-based microcapsules intended for textile applications
  50. Exploring the effect of khat (Catha edulis) chewing on the pharmacokinetics of the antiplatelet drug clopidogrel in rats using the newly developed LC-MS/MS technique
  51. A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water
  52. Cadmium (Cd) chloride affects the nutrient uptake and Cd-resistant bacterium reduces the adsorption of Cd in muskmelon plants
  53. Removal of H2S by vermicompost biofilter and analysis on bacterial community
  54. Structural cytotoxicity relationship of 2-phenoxy(thiomethyl)pyridotriazolopyrimidines: Quantum chemical calculations and statistical analysis
  55. A self-breaking supramolecular plugging system as lost circulation material in oilfield
  56. Synthesis, characterization, and pharmacological evaluation of thiourea derivatives
  57. Application of drug–metal ion interaction principle in conductometric determination of imatinib, sorafenib, gefitinib and bosutinib
  58. Synthesis and characterization of a novel chitosan-grafted-polyorthoethylaniline biocomposite and utilization for dye removal from water
  59. Optimisation of urine sample preparation for shotgun proteomics
  60. DFT investigations on arylsulphonyl pyrazole derivatives as potential ligands of selected kinases
  61. Treatment of Parkinson’s disease using focused ultrasound with GDNF retrovirus-loaded microbubbles to open the blood–brain barrier
  62. New derivatives of a natural nordentatin
  63. Fluorescence biomarkers of malignant melanoma detectable in urine
  64. Study of the remediation effects of passivation materials on Pb-contaminated soil
  65. Saliva proteomic analysis reveals possible biomarkers of renal cell carcinoma
  66. Withania frutescens: Chemical characterization, analgesic, anti-inflammatory, and healing activities
  67. Design, synthesis and pharmacological profile of (−)-verbenone hydrazones
  68. Synthesis of magnesium carbonate hydrate from natural talc
  69. Stability-indicating HPLC-DAD assay for simultaneous quantification of hydrocortisone 21 acetate, dexamethasone, and fluocinolone acetonide in cosmetics
  70. A novel lactose biosensor based on electrochemically synthesized 3,4-ethylenedioxythiophene/thiophene (EDOT/Th) copolymer
  71. Citrullus colocynthis (L.) Schrad: Chemical characterization, scavenging and cytotoxic activities
  72. Development and validation of a high performance liquid chromatography/diode array detection method for estrogen determination: Application to residual analysis in meat products
  73. PCSK9 concentrations in different stages of subclinical atherosclerosis and their relationship with inflammation
  74. Development of trace analysis for alkyl methanesulfonates in the delgocitinib drug substance using GC-FID and liquid–liquid extraction with ionic liquid
  75. Electrochemical evaluation of the antioxidant capacity of natural compounds on glassy carbon electrode modified with guanine-, polythionine-, and nitrogen-doped graphene
  76. A Dy(iii)–organic framework as a fluorescent probe for highly selective detection of picric acid and treatment activity on human lung cancer cells
  77. A Zn(ii)–organic cage with semirigid ligand for solvent-free cyanosilylation and inhibitory effect on ovarian cancer cell migration and invasion ability via regulating mi-RNA16 expression
  78. Polyphenol content and antioxidant activities of Prunus padus L. and Prunus serotina L. leaves: Electrochemical and spectrophotometric approach and their antimicrobial properties
  79. The combined use of GC, PDSC and FT-IR techniques to characterize fat extracted from commercial complete dry pet food for adult cats
  80. MALDI-TOF MS profiling in the discovery and identification of salivary proteomic patterns of temporomandibular joint disorders
  81. Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives
  82. Structure and some physicochemical and functional properties of water treated under ammonia with low-temperature low-pressure glow plasma of low frequency
  83. Mesoscale nanoparticles encapsulated with emodin for targeting antifibrosis in animal models
  84. Amine-functionalized magnetic activated carbon as an adsorbent for preconcentration and determination of acidic drugs in environmental water samples using HPLC-DAD
  85. Antioxidant activity as a response to cadmium pollution in three durum wheat genotypes differing in salt-tolerance
  86. A promising naphthoquinone [8-hydroxy-2-(2-thienylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione] exerts anti-colorectal cancer activity through ferroptosis and inhibition of MAPK signaling pathway based on RNA sequencing
  87. Synthesis and efficacy of herbicidal ionic liquids with chlorsulfuron as the anion
  88. Effect of isovalent substitution on the crystal structure and properties of two-slab indates BaLa2−xSmxIn2O7
  89. Synthesis, spectral and thermo-kinetics explorations of Schiff-base derived metal complexes
  90. An improved reduction method for phase stability testing in the single-phase region
  91. Comparative analysis of chemical composition of some commercially important fishes with an emphasis on various Malaysian diets
  92. Development of a solventless stir bar sorptive extraction/thermal desorption large volume injection capillary gas chromatographic-mass spectrometric method for ultra-trace determination of pyrethroids pesticides in river and tap water samples
  93. A turbidity sensor development based on NL-PI observers: Experimental application to the control of a Sinaloa’s River Spirulina maxima cultivation
  94. Deep desulfurization of sintering flue gas in iron and steel works based on low-temperature oxidation
  95. Investigations of metallic elements and phenolics in Chinese medicinal plants
  96. Influence of site-classification approach on geochemical background values
  97. Effects of ageing on the surface characteristics and Cu(ii) adsorption behaviour of rice husk biochar in soil
  98. Adsorption and sugarcane-bagasse-derived activated carbon-based mitigation of 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea-contaminated soils
  99. Antimicrobial and antifungal activities of bifunctional cooper(ii) complexes with non-steroidal anti-inflammatory drugs, flufenamic, mefenamic and tolfenamic acids and 1,10-phenanthroline
  100. Application of selenium and silicon to alleviate short-term drought stress in French marigold (Tagetes patula L.) as a model plant species
  101. Screening and analysis of xanthine oxidase inhibitors in jute leaves and their protective effects against hydrogen peroxide-induced oxidative stress in cells
  102. Synthesis and physicochemical studies of a series of mixed-ligand transition metal complexes and their molecular docking investigations against Coronavirus main protease
  103. A study of in vitro metabolism and cytotoxicity of mephedrone and methoxetamine in human and pig liver models using GC/MS and LC/MS analyses
  104. A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
  105. Erratum
  106. Erratum to: A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  107. Review Articles
  108. Sinoporphyrin sodium, a novel sensitizer for photodynamic and sonodynamic therapy
  109. Natural products isolated from Casimiroa
  110. Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review
  111. Evaluation of elastomeric heat shielding materials as insulators for solid propellant rocket motors: A short review
  112. Special Issue on Applied Biochemistry and Biotechnology 2019
  113. An overview of Monascus fermentation processes for monacolin K production
  114. Study on online soft sensor method of total sugar content in chlorotetracycline fermentation tank
  115. Studies on the Anti-Gouty Arthritis and Anti-hyperuricemia Properties of Astilbin in Animal Models
  116. Effects of organic fertilizer on water use, photosynthetic characteristics, and fruit quality of pear jujube in northern Shaanxi
  117. Characteristics of the root exudate release system of typical plants in plateau lakeside wetland under phosphorus stress conditions
  118. Characterization of soil water by the means of hydrogen and oxygen isotope ratio at dry-wet season under different soil layers in the dry-hot valley of Jinsha River
  119. Composition and diurnal variation of floral scent emission in Rosa rugosa Thunb. and Tulipa gesneriana L.
  120. Preparation of a novel ginkgolide B niosomal composite drug
  121. The degradation, biodegradability and toxicity evaluation of sulfamethazine antibiotics by gamma radiation
  122. Special issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  123. Insight into the cadmium and zinc binding potential of humic acids derived from composts by EEM spectra combined with PARAFAC analysis
  124. Source apportionment of soil contamination based on multivariate receptor and robust geostatistics in a typical rural–urban area, Wuhan city, middle China
  125. Special Issue on 13th JCC 2018
  126. The Role of H2C2O4 and Na2CO3 as Precipitating Agents on The Physichochemical Properties and Photocatalytic Activity of Bismuth Oxide
  127. Preparation of magnetite-silica–cetyltrimethylammonium for phenol removal based on adsolubilization
  128. Topical Issue on Agriculture
  129. Size-dependent growth kinetics of struvite crystals in wastewater with calcium ions
  130. The effect of silica-calcite sedimentary rock contained in the chicken broiler diet on the overall quality of chicken muscles
  131. Physicochemical properties of selected herbicidal products containing nicosulfuron as an active ingredient
  132. Lycopene in tomatoes and tomato products
  133. Fluorescence in the assessment of the share of a key component in the mixing of feed
  134. Sulfur application alleviates chromium stress in maize and wheat
  135. Effectiveness of removal of sulphur compounds from the air after 3 years of biofiltration with a mixture of compost soil, peat, coconut fibre and oak bark
  136. Special Issue on the 4th Green Chemistry 2018
  137. Study and fire test of banana fibre reinforced composites with flame retardance properties
  138. Special Issue on the International conference CosCI 2018
  139. Disintegration, In vitro Dissolution, and Drug Release Kinetics Profiles of k-Carrageenan-based Nutraceutical Hard-shell Capsules Containing Salicylamide
  140. Synthesis of amorphous aluminosilicate from impure Indonesian kaolin
  141. Special Issue on the International Conf on Science, Applied Science, Teaching and Education 2019
  142. Functionalization of Congo red dye as a light harvester on solar cell
  143. The effect of nitrite food preservatives added to se’i meat on the expression of wild-type p53 protein
  144. Biocompatibility and osteoconductivity of scaffold porous composite collagen–hydroxyapatite based coral for bone regeneration
  145. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  146. Effect of natural boron mineral use on the essential oil ratio and components of Musk Sage (Salvia sclarea L.)
  147. A theoretical and experimental study of the adsorptive removal of hexavalent chromium ions using graphene oxide as an adsorbent
  148. A study on the bacterial adhesion of Streptococcus mutans in various dental ceramics: In vitro study
  149. Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
  150. Special Issue on Chemistry Today for Tomorrow 2019
  151. Diabetes mellitus type 2: Exploratory data analysis based on clinical reading
  152. Multivariate analysis for the classification of copper–lead and copper–zinc glasses
  153. Special Issue on Advances in Chemistry and Polymers
  154. The spatial and temporal distribution of cationic and anionic radicals in early embryo implantation
  155. Special Issue on 3rd IC3PE 2020
  156. Magnetic iron oxide/clay nanocomposites for adsorption and catalytic oxidation in water treatment applications
  157. Special Issue on IC3PE 2018/2019 Conference
  158. Exergy analysis of conventional and hydrothermal liquefaction–esterification processes of microalgae for biodiesel production
  159. Advancing biodiesel production from microalgae Spirulina sp. by a simultaneous extraction–transesterification process using palm oil as a co-solvent of methanol
  160. Topical Issue on Applications of Mathematics in Chemistry
  161. Omega and the related counting polynomials of some chemical structures
  162. M-polynomial and topological indices of zigzag edge coronoid fused by starphene
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