Dynamic Characteristics of the Novel Strobilurin Fungicide SYP-3343

Food Chem. , 2014, 62 (15), pp 3343–3347. DOI: 10.1021/jf500392d. Publication Date (Web): March 24, 2014. Copyright © 2014 American Chemical Societ...
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Dynamic Characteristics of the Novel Strobilurin Fungicide SYP-3343 in Aerobic Soils Xun-Yue Liu, Xia Chen, Hai-Yan Wang, Ti-long Yang, Qing-Fu Ye,* and Xing-Cheng Ding* Institute of Nuclear Agricultural Sciences and Key Laboratory of Nuclear Agricultural Sciences of Ministry of Agriculture, Zhejiang University, Hangzhou, Zhejiang 310029, People’s Republic of China S Supporting Information *

ABSTRACT: SYP-3343, (E)-2-(2-((3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-yloxy)methyl)phenyl)-3-methoxyacrylate, is a newly developed strobilurin fungicide. However, the environmental behavior and fate of SYP-3343 in soil have not been welldocumented. In this study, 14C-labeled SYP-3343 was employed to investigate the dynamic characteristics in three typical soils under aerobic conditions. Radioactivity analysis after high-performance liquid chromatography (HPLC) showed that SYP-3343 degraded rapidly in the coastal soil with a half-life of 43.8 days. After incubation of 100 days, its extractable residues were greater than 76.0% and bound residues were less than 12.4%, indicating that SYP-3343 was not easy to accumulate in soils. The mineralization to 14CO2 reached 5.4% for acidic soil, 2.8% for neutral soil, and 1.7% for alkaline soil, suggesting that it was difficult to cleave the pyrazole ring completely. In addition, dynamic characteristics of SYP-3343 in sterile and non-sterile loamy soil showed that soil microbes affected SYP-3343 residue in soil and could accelerate the process of degradation and mineralization. KEYWORDS: SYP-3343, aerobic degradation, extractable residue, bound residue, mineralization

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INTRODUCTION Over the last 60 years, pesticides have been widely used to increase crop production. Despite the merits of these chemicals to protect crops, they are also well-known to cause considerable negative effects on non-targeted organisms.1−4 Because of the extensive use of pesticides in crops, malathion and chlorinated hydrocarbons, including lindane and dichlorodiphenyltrichloroethane (DDT), have been detected in mammals.5,6 Evaluating the hazards of novel pesticides to the agroecosystem is essential for its safe usage. Soil is one of the major sites where pesticides are absorbed. It is therefore obligatory to study the behavior of pesticides in soils, such as characteristics of their residue, degradation, and fate, to assess the safety of their application.7,8 Studies employing 14C-labeled pesticides can easily show the dissipation of parent compounds, the rates of conversion into extractable residue (ER) and bound residue (BR), and the ratio of mineralization to CO2 after application.9 The ER is defined as the fraction that is extractable by organic solvents, which has high bioavailability and is susceptible to degradation.10 The formation of BR may cause a significant loss of bioavailability that is known as an important detoxification process in soil,11 but it is also treated as a potential risk for the environment if it is released from soil.12 Mineralization is a pathway by which the parent compounds completely degrade into CO2 and detoxify. The Uniform Principles of Europe declare that, if the BR of a pesticide is larger than 70% with less than 5% mineralization to CO2 in laboratory tests, the pesticide should not be authorized unless it can be demonstrated that no accumulation of residues occurs in the soil under field conditions.13 The strobilurins are one class of fungicidal compounds isolated and modified from several basidomycetes species that grow on decaying plants, and they have been used as agrochemicals for more than 30 years in many countries.14 © 2014 American Chemical Society

Strobilurins take effect by blocking the electron transfer between cytochrome b and cytochrome c1 by binding at the Qo site of cytochrome b. Increased resistance toward strobilurins has been observed in field applications, which spurred the development of new strobilurins for effective control of fungi on plants. SYP-3343 is a new strobilurin fungicide developed by Shenyang Research Institute of Chemical Industry, China. Previous studies indicated that the compound exhibits strong fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Pseudoperonospora cubensis, Erysiphe graminis, and Magnaporthe grisea (rice blast). Temporary registration for the compound has also been obtained in China for control of cucumber downy mildew at a rate of 80−100 g of active ingredient/hectare.15,16 However, the dynamic characteristics of ER, BR, and mineralization of SYP3343 in soil are not well-understood. In the present study, we used three types of wellcharacterized soils to investigate the ER, BR, and mineralization of SYP-3343 under aerobic conditions as well as the dissipation of SYP-3343 parent compond by the 14C-tracing method. Furthermore, a sterile loamy soil was selected to investigate the influence of soil microbial activity on the ER, BR, and mineralization of SYP-3343.

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MATERIALS AND METHODS

Chemicals. SYP-3343 with a 14C-labeled pyrazole ring (Figure 1) was synthesized and purified by the Institute of Nuclear Agricultural Sciences, Zhejiang University, Hangzhou, China. Analysis of the high-

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C ER Analysis. The soil samples were extracted using four solvents (50 mL) in sequence, 0.01 M CaCl2, acetonitrile/water (9:1, v/v), methanol, and dichloromethane, by shaking for 24 h and followed by centrifugation at 4000 rpm for 10 min, corresponding to the similar method reported by Mordaunt et al.21 Subsequently, additional one or two extracting processes were conducted using methanol until no radioactivity could be detected in the extracts. After these exhaustive solvent extractions, the radioactivity of each supernatant was measured by a liquid scintillation counter (LSC, Wallac-1414, Wallac Co., Turku, Finland) using scintillation cocktail I. Dissipation of Parent Compound Analysis. ER extracts were combined and concentrated on the vacuumed rotary evaporator (Eyela SB-1000, Eyela, Tokyo, Japan) at 37 °C, then recovered in 10 mL of methanol (chromatographic grade), and further condensed to 1.0 mL. The final extracts were passed through a 0.22 μm filter for HPLC analysis. A 20 μL aliquot of the final sample was injected into a Waters 2695 system (Waters 2998 photodiode array detector, Waters, Milford, MA) with a Diamonsil C18 column (5 μm, 250 × 4.6 mm, Dikama Technologies, Lake Forrest, CA). The column temperature was 28 ± 1 °C. The mobile phase was composed of A (methanol + 0.1% ethylic acid) and B (H2O + 0.1% ethylic acid). The elution process was carried out under a gradient elution [A/B (%): 20:80 for 0 min, 75:25 for 20 min, 75:25 for 60 min, 100:0 for 65 min, 100:0 for 70 min, 0:100 for 75 min, 20:80 for 80 min] at a flow rate of 1.0 mL/ min. A standard sample was used to confirm the retention time of the parent SYP-3343. Aliquots of the eluent were collected in a 20 mL glass scintillation vial at 1 min intervals. A total of 10 mL of scintillation cocktail I was added to each collected eluent for the radioactivity measurement by LSC. 14 C-BR Analysis. After 4−6 shaking extraction steps, the remaining soil pellets were placed in tubes and put inside the fume hood overnight to remove the residual solvent. The samples were then thoroughly mixed, and 0.5 g of soil was used for combustion with a biological oxidizer (OX-600, R.J. Harvey Instrument Corp., Hilldale, NJ). The oxidation procedure was held on for 4 min at 900 °C for combustion and 680 °C for catalysis, using scintillation cocktail II to absorb 14CO2. The recovery efficiency of this procedure was more than 91.3%, measured by comparing the combustion of 14C-SYP-3343 with a known radioactivity. Mineralization Analysis. The measurement of mineralization was conducted by forcing air through the sample for 1.5 h/day to remove CO2, which could be absorbed by two flasks of NaOH solution during the whole experimental period. This solution was changed every 5 days and stored in a refrigerator (4 °C) for further use of the radioactivity measurement. The two traps were combined and adjusted to a defined volume with distilled water. Then, a 1.0 mL aliquot was drawn, and its radioactivity was measured with 10 mL of scintillation cocktail I. Statistical Analysis. The dissipation of parent 14C-SYP-3343 was analyzed using the first-order regression model Ct = C0 exp(−kt), where C0 is the initial quantity, Ct is the quantity at time t, and k is the degradation constant. The half-life (t1/2) value was calculated as ln 2/k. All of the experiments were conducted in triplicate, and the standard deviations (mean ± standard deviation) presented in the text were calculated from the repeated measurements. Statistical analysis by one-way analysis of variance (ANOVA) was performed with SPSS 20.0 (IBM Corporation, Armonk, NY).

Figure 1. Chemical structure of SYP-3343.

performance liquid chromatography−liquid scintillation counting (HPLC−LSC) and thin-layer chromatography−isotope imaging (TLC−IIA) data indicated that both the radiochemical and chemical purities of the fungicide were over 98% and its specific activity was 5.042 ± 0.076 mCi/mmol.17,18 2,5-Diphenyloxazole (PPO) and 1,4dis-[2′-(5′-phenyloxazolyl)]-benzene (POPOP) were of scintillation grade, purchased from Acros Organics (Geel, Belgium), and were used to prepare the scintillation cocktails as below: scintillation cocktail I, PPO (7.0 g) and POPOP (0.5 g) dissolved in a mixture of dimethyl benzene (650 mL) and glycol ether (350 mL); scintillation cocktail II, PPO (7.0 g) and POPOP (0.5 g) dissolved in a mixture of dimethyl benzene (600 mL), glycolether (225 mL), and ethanolamine (175 mL). The other chemical solvents were all analytical-grade. Soil Preparation. Three representative soils were collected from the surface layers (0−20 cm) of agricultural regions in different areas of China, none of which had been previously applied with SYP-3343. The physical and chemical properties of these soils were shown in Table 1. The soil samples were air-dried, mixed, and sieved through a 1 mm sieve. The basic properties were determined using the standard methods.19 To examine the influence of soil microbes on ER, BR, and mineralization of SYP-3343, a subsample of loamy soil was sterilized through irradiation by Cobalt-60 at an absorbed dose of 6 kGy/100 g of soil. Incubation and Treatments. The 14C-labeled SYP-3343 was employed to determine the dynamic characteristics of SYP-3343 in soils. The incubation procedures were based on OECD guideline 307.20 Briefly, after 300 g of soil sample (dry weight) was adjusted to a water holding capacity (WHC) of approximately 40% by adding distilled water, samples were pre-incubated in a dark cultivation cabinet at 25 ± 1 °C for 14 days to help the microbes adapt to the environmental change. An appropriate volume of the prepared 14CSYP-3343 in methanol solution (∼7.4 × 105 Bq/sample) was added to each sample slowly. The treated samples were thoroughly mixed and placed in a fume hood to completely remove the methanol. Distilled water was added to readjust the soil moisture to about 60% WHC. The samples were incubated independently in the dark at 25 ± 1 °C under a continuous airflow. During the course of cultivation, moisture was maintained at 60% WHC using the weighing method. Each incubated flask was connected to a series of small flasks (see Figure S1 of the Supporting Information). First, two flasks (30 mL, 5.0 M NaOH) were set for scrubbing the inlet CO2, while the following distilled water flask was used for maintaining constant soil moisture. Besides, the 1.0 M H2SO4 and glycol traps were used for absorbing volatile agents, and last two 5.0 M NaOH traps were set for trapping the released 14CO2. At different time intervals (0, 5, 10, 20, 30, 45, 60, 75, and 100 days after treatment), the treated soils (10 g, dry weight) were sampled (three replicates) to subject the following extractions. The sterilized soil sample was analyzed under the same protocol, but all procedures were performed in a sterile environment.

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RESULTS AND DISCUSSION Total 14C Material Mass Balance. The total recovered 14C was calculated as the sum of 14C in continuous extraction steps,

Table 1. Basic Physical and Physicochemical Properties of the Selected Soils

a

number

soil type

pH

OMa (%)

CECb (mequiv 100 g−1)

silt (%)

sand (%)

clay (%)

S1 S2 S3

coastal soil loamy soil red soil

8.23 6.95 5.53

1.23 2.11 2.65

11.77 10.65 8.93

31.32 36.32 33.25

26.32 20.98 21.01

42.36 42.70 45.75

OM = organic matter. bCEC = cation-exchange capacity. 3344

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BR, and CO2 in mineralization after treatment. The total 14C material mass balance was calculated by the total recovered 14C to the initial added 14C, ranging from 95.8 ± 2.9 to 103.5 ± 3.7% (n = 3) in the four tested soils. The high 14C recoveries indicated that the procedure used for measuring the different residues was feasible. Formation of the ER and Degradation of the Parent Compound. The decrease of ER over the incubation period was shown in Figure 2. In the initial 10 days of incubation, ER

Figure 3. Dissipation of parent SYP-3343 in aerobic soils (bars represent ±standard error of the mean).

Information), which indicated that the degradation rates of SYP-3343 might be attributed to both the soil properties and its surroundings, such as pH, organic matter (OM), cationexchange capacity (CEC), soil particles, temperature, and soil moisture. It is noteworthy that the half-life of the sterile S2 was about 2 times longer than the non-sterile S2 (169.0 versus 80.6 days), suggesting that microbes played an important role in its degradation. In S3, it has a calculated half-life of 123.7 days that exceeded the total incubation time. In general, degradation of parent SYP-3343 followed the order of S1 > S2 > S3 > S2sterile. Previous studies showed that many chemicals (e.g., naproxen and carbamazepine) under different soil conditions had different rates of degradation.23 Thus, it was likely to infer that soil enzymes, microbes, and sediments could selectively influence the performance of chemicals in soil.24 The long-term dissipation may cause a potential hazard because of the accumulation in the future. Formation of BRs. In the risk assessment of pesticides, BR is always used in the description of dissipation kinetics.25 The BR fraction after 30 days of treatment treated with SYP-3343 increased rapidly in S1 and S2, but in the S2-sterile soil, no significant increase of BR was observed (p > 0.05). Furthermore, the BR in S3 was found to increase slightly until 1.73% at the end of incubation, which was much lower than those in S1 and S2. The formation of BR of many pesticides has been reported to be mediated by pH and CEC.11 S3 has a low pH and CEC that may contribute to its low binding affinity. After 45 days of incubation, a significant difference between S2 and S2-sterile was observed (p < 0.01), indicating that soil microbes could affect the formation of BR. As shown in Figure 4, after incubation of 100 days, the BR followed the order of S1 (alkaline soil, 12.4%) > S2 (neutral soil, 9.9%) > S2-sterile (6.0%) > S3 (acid soil, 1.7%). These results demonstrated that SYP-3343 could be absorbed in the soil and increase with time. Therefore, the BR level reported here, which is much lower than 70%, satisfied the nonaccumulation uniform principles demonstrated in laboratory tests.13 The formation of BR was accompanied by degradation, which was also found in other chemicals, such as nonylphenol.26 Mineralization. It could be seen from Figure 5 that the mineralization of SYP-3343 increased gradually with time in the tested soils, indicating that the pyrazole ring could be gradually

Figure 2. ER of SYP-3343 in aerobic soils (bars represent ±standard error of the mean).

was detected up to about 95% after the four extraction steps. A significant decrease of ER was observed in the coastal soil (S1); after incubation for 100 days, the ER ratio was determined to be 76.79 ± 1.89%. However, the ER level was almost constant in the red soil (S3), showing no significant decrease within the incubation time (p > 0.05), approximately 93.79 ± 3.55%, at the end of the incubation. In addition, ER in the sterilized loamy soil S2 (S2-sterile) was 90.45 ± 1.32%, which was slightly higher than ER in non-sterilized S2 (86.91 ± 2.45%), indicating that soil microbes may promote the dissipation of ER. However, only an inconspicuous decrease of ER in S3, from 98.5 ± 3.63 to 93.79 ± 3.55%, was observed over the incubation period. The ER levels in three tested soils were S1 < S2 < S2-sterile < S3. Possibly, the time dependence of the ER decrease can be attributed to the transformation into BR and mineralization to CO2. Because of the high extraction rate, it may have potential harm to the downstream farm or water through irrigation. The above findings implied the specific type of soil needed to be considered for the use of fungicide in the context of environmentally friendly usage. Radioactivity analysis after HPLC fractionation showed that the degradation of SYP-3343 was in accordance with the biexponential equation (r2 > 0.90; see Table S1 of the Supporting Information). The remaining parent compound was 17.8 ± 1.62, 39.2 ± 1.19, 65.5 ± 4.52, and 56.6 ± 1.58% of the applied amount in S1, S2, S2-sterile, and S3 at the end of incubation, respectively (Figure 3), which suggested that the degradation of SYP-3343 in S1 was fastest compared to S2, S2-sterile, and S3. A previous study found that the half-life of SYP-3343 in soil under field conditions was only 2.6−2.7 days.22 However, the half-lives in the four-treated soils ranged from 43.8 to 169.0 days under lab conditions (see Table S1 of the Supporting 3345

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itself or its metabolites should deserve more attention. Therefore, more effective data should be acquired in the future for its environmentally friendly use.

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ASSOCIATED CONTENT

* Supporting Information S

Incubation setup (Figure S1) and first-order rate constants (k), half-lives (t1/2), and coefficients of determination (r2) describing dissipation of the SYP-3343 parent compound in different soils (Table S1). This material is available free of charge via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: [email protected]. Funding

Figure 4. BR of SYP-3343 in aerobic soils (bars represent ±standard error of the mean).

This work was financially supported by the special fund for Agro-scientific Research in the Public Interest (201103007), the Fundamental Research Funds for the Central Universities (2013FZA6011), and the Project of Science Technology Department of Zhejiang Province (2010R50033). Xun-Yue Liu thanks the Chinese Scholarship Council (CSC) for financial support. Notes

The authors declare no competing financial interest.

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REFERENCES

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Figure 5. Mineralization of SYP-3343 in aerobic soils (Bars represent ±standard error of the mean).

opened under the present experimental conditions. The ratio of SYP-3343 mineralized to 14CO2 was only 0.03−0.06% after 5 days of incubation. Despite the differences in soil properties, the mineralization ratio was lower than 5.4% in all treatments, suggesting that the cleavage of the pyrazole ring was difficult, so that the parent compound or metabolites of SYP-3343 might remain in aerobic soils for a prolonged period. After 100 days of incubation, the mineralization followed the pattern: S1 > S2 > S3 > S2-sterile. A mineralization ratio of 2.83% was obtained in S2, which was about 2.5 times larger than that in S2-sterile (Figure 5). These findings indicated that soil microbes played an important role in SYP-3343 mineralization. Generally, the degree of mineralization can be affected by microbes and soil properties. A similar phenomenon was observed in the pesticide ZJ0273.27 Because mineralization is regarded as one of the detoxification pathways, the above results indicated that SYP-3343 was not prone to degrade completely and might remain in soil as either the parent compound or a mixture of the parent compound and metabolites. Although it fits the non-accumulative principle stated by the Commission of the European Communities, it is not recommended to use in red soil. The potential toxicity of 3346

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and release of tetrabromobisphenol A in soil during sequential anoxic− oxic incubation. Environ. Sci. Technol. 2013, 47, 8348−8354. (13) Commission of the European Communities (CEC). Directive 97/57, Establishing Annex VI (Uniform Principles to Directive 91/414; CEC, Directorate General for Agriculture, DG VI B II-1-Brussels: Brussels, Belgium, 1997. (14) Sauter, H.; Steglich, W.; Anke, T. Strobilurins: Evolution of a new class of active substances. Angew. Chem., Int. Ed. 1999, 38 (10), 1328−1349. (15) Li, M.; Liu, C. L.; Yang, J. C.; Zhang, J. B.; Li, Z. N.; Zhang, H.; Li, Z. M. Synthesis and biological activity of new (E)-α(methoxyimino)benzeneacetate derivatives containing a substituted pyrazole ring. J. Agric. Food Chem. 2010, 58, 2664−2667. (16) Wang, L.; Li, B. J.; Xiang, W. S.; Shi, Y. X.; Liu, C. L. Control effects of pyraoxystrobin on cucumber powdery mildew. Agrochemicals 2008, 47 (5), 378−380 (in Chinese). (17) Li, M.; Li, L.; Liu, C. L.; Li, Z. M.; Li, Z. N.; Shi, N. G. Proc. 7th Chin. Annu. Meet. Innovative Pestic. 2009, 242−246. (18) Liu, X. Y.; Ye, Q. F.; Kan, D. L.; Zhang, Z.; Ding, X. C. Synthesis of carbon-14 labeled pyraoxystrobin, a novel fungicide. J. Labelled Compd. Radiopharm. 2011, 54, 780−782. (19) Nelson, D. W.; Sommers, L. Chemical and microbiological properties. In Methods of Soil Analysis, Part 2; Page, A. L., Eds.; American Society of Agronomy: Madison, WI, 1982; pp 539−579. (20) Organization for Economic Co-operation and Development (OECD). Aerobic and anaerobic transformation in soil, no. 307. OECD Guidelines for the Testing of Chemicals; OECD: Paris, France, 2002. (21) Gee, G. W.; Bauder, W. Partical-size analysis. Physical and mineralogical methods. In Methods of Soil Analysis, Part 1; Klute, A., Eds.; Soil Science Society of America: Madison, WI, 1986; pp 383− 412. (22) Liu, Y. P.; Sun, H. B.; Zeng, F. J.; Liu, J. M.; Xu, Y. L.; Wang, S. W. Study on residual dynamics of SYP-3343 in cucumber and soil. Guangdong Agric. Sci. 2010, 9, 46−47 (in Chinese). (23) Lin, K.; Gan, J. Sorption and degradation of wastewaterassociated non-steroidal anti-inflammatory drugs and antibiotic in soils. Chemosphere 2011, 83, 240−246. (24) Li, J. Y.; Dodgen, L.; Ye, Q. F.; Gan, J. Degradation kinetics and metabolites of carbamazepine in soil. Environ. Sci. Technol. 2013, 47, 3678−3684. (25) Barriuso, E.; Benoit, P.; Dubus, I. Formation of pesticide nonextractable (bound) residues in soil: Magnitude, controlling factors and reversibility. Environ. Sci. Technol. 2008, 42, 1845−1854. (26) Liu, J.; Shan, J.; Jiang, B. Q.; Wang, L. H.; Yu, B.; Chen, J. Q.; Guo, H. Y.; Ji, R. Degradation and bound-residue formation of nonylphenol in red soil and the effects of ammonium. Environ. Pollut. 2014, 186, 83−89. (27) Wang, W.; Ye, Q. F.; Ding, W.; Han, A. L.; Wang, H. Y.; Lu, L.; Gan, J. Influence of soil factors on the dissipation of a new pyrimidynyloxybenzoic herbicide ZJ0273. J. Agric. Food Chem. 2010, 58, 3062−3067.

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NOTE ADDED AFTER ASAP PUBLICATION There was a mistake in the chemical name for SYP-3343 ((E)2-(2-((3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-yloxy) methyl)phenyl)-3-methoxyacrylate) in the first sentence of the formula in the abstract, and incorrect reference citations in the first and second paragraph of the Materials and Methods section of the version of this article published April 2, 2014. The correct version published April 16, 2014.

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