Skip to main content
SpringerLink
Log in

Study on the Hydrolysis Kinetics of Dimethyl Disulfide

  • Published:
Water, Air, & Soil Pollution Aims and scope Submit manuscript

Abstract

Dimethyl disulfide (DMDS) is a new soil fumigant that is considered a good alternative to methyl bromide due to its high activity toward soil-borne pests, with no ozone-depleting potential. The correlative literature for the study of DMDS and its environmental fate is limited. The hydrolysis kinetics of DMDS were studied in buffered aqueous solutions within a pH of 5, 7, and 9, temperature at 15, 25, 45, and 65 °C, and in natural water samples at an ambient temperature of 25 °C. The results showed that DMDS hydrolysis rates were accelerated by increases in pH and temperature. The calculated half-lives of DMDS hydrolysis in the solutions of pH 5, 7, and 9 were 13.91, 10.81, and 10.52 days, respectively at 25 °C, and the trend showed that DMDS hydrolyzed faster in neutral or mild alkali conditions than in acidic solutions at the same temperature. The calculated half-lives of DMDS hydrolysis in the solutions at 15, 25, 45, and 65 °C were 15.78, 10.81, 9.78, and 7.72 days at pH = 7, respectively. There existed no obvious correlations between the activation energies of DMDS hydrolysis and temperatures. However, the activation entropy absolute values of DMDS hydrolysis increased with increasing temperatures, suggesting that the hydrolysis of DMDS in aqueous solutions was driven by activation entropy. The hydrolysis rates of DMDS in natural water samples are as follows: rice paddy field water > Grand Canal water > tap water. Sterilization of three kinds of natural water samples showed that biodegradation accounted for 4.08, 21.52, and 8.82% in tap water, paddy field water, and Grand Canal water, respectively. This research result has important implications in the scientific evaluation of DMDS.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • Archer, S., & Suter, C. M. (1952). The preparation of some 1-alkylamino-and dialkylaminoalkylaminothiaxanthones1. Journal of the American Chemical Society, 74(17), 4296–4309.

    Article  CAS  Google Scholar 

  • Auger, J., Lecomte, C., & Thibout, E. (1989). Leek odor analysis by gas chromatography and identification of the most active substance for the leek moth, Acrolepiopsis assectella. Journal of Chemical Ecology, 15, 1847–1854.

    Article  CAS  Google Scholar 

  • Cabrera, J. A., Wang, D., Gerik, J. S., & Gan, J. (2014). Spot drip application of dimethyl disulfide as a post-plant treatment for the control of plant parasitic nematodes and soilborne pathogens in grape production. Pest management science., 70(7), 1151–1157.

    Article  CAS  Google Scholar 

  • Culpepper, S., Sosnoskie, L., Rucker, K., Tankersley, B., Langston, D., Webster, T., & Upchurch, W. (2008). DMDS or the 3-way: which is more effective in Georgia? Proc. Annu. Intl. Res. Conf. on Methyl Bromide Alternatives and Emissions Reductions. Methyl Bromide Alternatives Outreach.

  • Gan, J., Yates, S. R., Papiernik, S., & Crowley, D. (1998). Application of organic amendments to reduce volatile pesticide emissions from soil. Environmental Science & Technology, 32(20), 3094–3098.

    Article  CAS  Google Scholar 

  • Gao, S., Ajwa, H., Qin, R., Stanghellini, M., & Sullivan, D. (2013). Emission and transport of 1,3-dichloropropene and chloropicrin in a large field tarped with VaporSafe TIF. Environmental Science & Technology, 47, 405–411.

    Article  CAS  Google Scholar 

  • García-Méndez, E., García-Sinovas, D., Becerril, M., De Cal, A., Melgarejo, P., Martínez-Treceño, A., & López-Aranda, J. M. (2008). Chemical alternatives to methyl bromide for weed control and runner plant production in strawberry nurseries. HortScience, 43(1), 177–182.

  • Gillis, M. (2003). DMDS 2003 field trials in California, in Annu International Research Conference on Methyl Bromide Alternatives and Emissions Reductions. Methyl Bromide Alternatives Outreach, San Diego.

  • Guo, M., Papiernik, S. K., Zheng, W., & Yates, S. R. (2004). Effects of environmental factors on 1, 3-dichloropropene hydrolysis in water and soil. Journal of Environmental Quality, 33(2), 612–618.

    Article  CAS  Google Scholar 

  • Han, D., Wang, Q., Liu, P., Fang, W., Yan, D., & Cao, A. (2016). Dimethyl disulphide residue analysis and degradation kinetics determination in soil using gas chromatography–mass spectrometry. International Journal of Environmental Analytical Chemistry, 96(7), 694–704.

    Article  CAS  Google Scholar 

  • Higgins, M. J., et al. (2003). Mechanisms of volatile sulfur compound and odor production in digested biosolids. Proceedings of the Water Environment Federation, 2003(1), 993–1006.

    Article  Google Scholar 

  • Ito, T., Miyaji, T., Nakagawa, T., & Tomizuka, N. (2007). Degradation of dimethyl disulfide by Pseudomonas fluorescens strain 76. Bioscience, Biotechnology, and Biochemistry, 71(2), 366–370.

    Article  CAS  Google Scholar 

  • Jeffers, P. M., and Wolfe, N. L. (1997). Hydrolysis of methyl bromide, ethyl bromide, chloropicrin, 1, 4-dichloro-2-butene, and other halogenated hydrocarbons. Chapter 4, pp 32–41.

  • Le Bechec, M., Costarramone, N., Fouillet, T., Charles, P., Pigot, T., Bégué, D., & Lacomb, S. (2015). Photocatalytic films for soil fumigation: Control of dimethyl disulfide concentration after fumigation. Applied Catalysis B: Environmental, 178, 192–200.

    Article  CAS  Google Scholar 

  • Liu, B., McConnell, L. L., & Torrents, A. (2001). Hydrolysis of chlorpyrifos in natural waters of the Chesapeake Bay. Chemosphere, 44(6), 1315–1323.

    Article  CAS  Google Scholar 

  • Minuto, A., Gullino, M. L., Lamberti, F., et al. (2006). Application of an emulsifiable mixture of 1, 3-dichloropropene and chloropicrin against root knot nematodes and soilborne fungi for greenhouse tomatoes in Italy. Crop Protection, 25(12), 1244–1252.

    Article  CAS  Google Scholar 

  • Mulay, P. R., Cavicchia, P., & Watkins, S. M. (2016). Acute illness associated with exposure to a new soil fumigant containing dimethyl disulfide—Hillsborough County, Florida, 2014. Journal of Agromedicine, 21(4), 373–379.

    Article  Google Scholar 

  • Olson, S. M. & Rich, J. (2007). Efficacy of Paladin (DMDS) as a soil fumigant for tomato and cantaloupe production. Proc. Annu. Intl. Res. Conf. on Methyl Bromide Alternatives and Emissions Reductions. Methyl Bromide Alternatives Outreach.

  • Pesticide Properties Database, (n.d.) University of Hertfordshire https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/2886.htm

  • Product label: Paladin; Arkema, Inc. 2012. King of Prussia, PA. EPA registration number 55050–4. https://www.epa.gov/soil-fumigants/soil-fumigant-labels-dimethyl-disulfide-dmds

  • Qin, R., Gao, S., Ajwa, H., & Hanson, B. D. (2016). Effect of application rate on fumigant degradation in five agricultural soils. Science of the Total Environment, 541, 528–534.

    Article  CAS  Google Scholar 

  • Reeves, C. E., & Penkett, S. A. (1993). An estimate of the anthropogenic contribution to atmospheric methyl bromide. Geophysical Research Letters, 20, 1563–1566.

    Article  CAS  Google Scholar 

  • Reichert, K., Lipski, A., Pradella, S., Stackebrandt, E., & Altendorf, K. (1998). Pseudonocardia asaccharolytica sp. nov. and Pseudonocardia sulfidoxydans sp. nov., two new dimethyl disulfide-degrading actinomycetes and emended description of the genus Pseudonocardia. International Journal of Systematic and Evolutionary Microbiology, 48(2), 441–449.

    CAS  Google Scholar 

  • Smith, N. A., & Kelly, D. P. (1988). Isolation and physiological characterization of autotrophic sulphur bacteria oxidizing dimethyl disulphide as sole source of energy. Microbiology, 134(6), 1407–1417.

    Article  CAS  Google Scholar 

  • Solomon, S., & Ravishankara, A. R. (1992). Atmospheric lifetime and ozone depletion potentials of methyl bromide (CHaBr) and dibromomethane (CH2Br2). Geophysical Research Letters, 19(20), 2059–2062.

    Article  Google Scholar 

  • Sondhia, S. (2009). Leaching behaviour of metsulfuron in two texturally different soils. Environmental Monitoring and Assessment, 154(1), 111–115.

    Article  CAS  Google Scholar 

  • U.S. Food and Drug Administration. (2015). Code of Federal Regulations: 21 CFR 172.515, April 1, 2015. http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?FR=172.515.

  • United Nations Environment Programme (UNEP). (1995). 1994 Report of the Methyl Bromide Technical Options Committee. United Nations Headquarters. Ozone Secretarit. P.O. Box 30552 Nairobi.

  • Vriens, B., Lenz, M., Charlet, L., Charlet, L., Berg, M., & Winkel, L. H. (2014). Natural wetland emissions of methylated trace elements. Nature Communications, 5, 3035.

    Article  Google Scholar 

  • Yin, F., Grosjean, D., & Seinfeld, J. H. (1990). Photooxidation of dimethyl sulfide and dimethyl disulfide. I: Mechanism development. Journal of Atmospheric Chemistry, 11(4), 309–364.

    Article  CAS  Google Scholar 

  • Zhang, Q., & Pehkonen, S. O. (1999). Oxidation of diazinon by aqueous chlorine: kinetics, mechanisms, and product studies. Journal of Agricultural and Food Chemistry, 47(4), 1760–1766.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by the National Natural Science Foundation Project of China (No. 31572035).

Author information

Authors and Affiliations

  1. State key Laboratory for Biology of Plant Disease and Insect Pest, Institute of Plant Protection of Chinese Academy of Agricultural Sciences, Beijing, 100193, China

    Dawei Han, Dongdong Yan, Aocheng Cao, Wensheng Fang, Xianli Wang, Zhaoxin Song, Yuan Li, Canbin Ouyang, Meixia Guo & Qiuxia Wang

  2. Laboratory of Phytopathology, University of Liège, Gembloux Agro-BioTech, Passage des déportés, 2, 5030, Gembloux, Belgium

    Zhaoxin Song

Authors
  1. Dawei Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dongdong Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aocheng Cao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wensheng Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xianli Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhaoxin Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yuan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Canbin Ouyang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Meixia Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Qiuxia Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qiuxia Wang.

Additional information

Danwei Han and Dongdong Yan are co-authors

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Han, D., Yan, D., Cao, A. et al. Study on the Hydrolysis Kinetics of Dimethyl Disulfide. Water Air Soil Pollut 228, 234 (2017). https://doi.org/10.1007/s11270-017-3406-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11270-017-3406-5

Keywords

Search

Navigation