Skip to main content
Log in

Oleoyl-carboxymethyl chitosan as a new carrier agent for the rotenone pesticide

  • Original Paper
  • Published:
Environmental Chemistry Letters Aims and scope Submit manuscript

Abstract

Rotenone is an active ingredient that has been widely used as pesticide. However, rotenone is poorly soluble in water. Therefore, a water-soluble carrier is needed. Here, we synthesised, characterised and applied oleoyl-carboxymethyl chitosan for the first time as a carrier agent for rotenone. Oleoyl-carboxymethyl chitosan is soluble in acidic, neutral and basic media. The critical micelle concentration of oleoyl-carboxymethyl chitosan is 0.096 mg/mL. Oleoyl-carboxymethyl chitosan formed self-aggregates and exhibited spherical shape with the values of 35.5–66.4 nm. We studied the encapsulation efficiency and loading capacity of oleoyl-carboxymethyl chitosan micelles with different weight ratios of oleoyl-carboxymethyl chitosan to rotenone. We found an encapsulation efficiency of 97 % and a loading capacity of 0.97 % for oleoyl-carboxymethyl chitosan/rotenone 100:1 w/w. Oleoyl-carboxymethyl chitosan released 96.00 % of the rotenone loaded within 50 h. Overall, our findings show the feasibility of oleoyl-carboxymethyl chitosan as a novel water-solubilising agent for pesticide formulations.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Antoniou J, Liu F, Majeed H, Zhoung F (2015) Characterization of tara gum edible films incorporated with bulk chitosan and chitosan nanoparticles: a comparative study. Food Hydrocoll 44:309–319

    Article  CAS  Google Scholar 

  • Bashan Y, de-Bashan LE, Prabhu SR, Hernandez JP (2014) Advances in plant growth-promoting bacterial inoculants technology: formulations and practical perspectives (1998–2013). Plant Soil 378:1–33

    Article  CAS  Google Scholar 

  • Castro MJL, Ojeda C, Cirelli AF (2014) Advances in surfactants for agrochemicals. Environ Chem Lett 12(1):85–95

    Article  CAS  Google Scholar 

  • Fu J, Cai Z, Gong Y, Reilly SEO, Hao X, Zhao D (2015) A new technique for determining critical micelle concentrations of surfactants and oil dispersants via UV absorbance of pyrene. Colloids Surf A 484:1–8

    Article  CAS  Google Scholar 

  • Hill DS (2008) Pests of crops in warmer climates and their control. Springer, Netherlands, pp 47–49

    Book  Google Scholar 

  • Hu L, Xia J, Zhan SL, Huang XD, Xu HH (2006) The preparation and characterizations of rotenone cyclodextrin inclusion complex the bioactivity against Bursaphelenchus xylophilus. J East China Norm Univ Nat Sci Ed 23:164–168

    Google Scholar 

  • Huo M, Zhang Y, Zhou J, Zou A, Yu D, Wu Y, Li H (2010) Synthesis and characterization of low-toxic amphiphilic chitosan derivatives and their application as micelle carrier for antitumor drug. Int J Pharm 394(1–2):162–173

    Article  CAS  Google Scholar 

  • Kah M, Machinski P, Koerner P, Tiede K, Grillo R, Fraceto LF (2014) Analysing the fate of nanopesticides in soil and the applicability of regulatory protocols using a polymer-based nanoformulation of atrazine. Environ Sci Pollut Res 21:11699–11707

    Article  CAS  Google Scholar 

  • Lao SB, Zhang ZX, Xu HH, Jiang GB (2010) Novel amphiphilic chitosan derivatives: synthesis, characterization and micellar solubilisation of rotenone. Carbohydr Polym 82:1136–1142

    Article  CAS  Google Scholar 

  • Li YY, Chen XG, Yu LM, Wang SX, Sun GZ, Zhou HY (2006) Aggregation of hydrophobically modified chitosan in solution and at the air–water interface. J Appl Polym Sci 102:1968–1973

    Article  CAS  Google Scholar 

  • Li Y, Zhang S, Meng X, Chen X, Ren G (2011) The preparation and characterization of a novel amphiphilic oleoyl-carboxymethyl chitosan self-assembled nanoparticles. Carbohydr Polym 83:130–136

    Article  CAS  Google Scholar 

  • Li W, Peng H, Ning F, Yao L, Luo M, Zhao Q, Zhu X, Xiong H (2014) Amphiphilic chitosan derivatives-based core-shell micelles: synthesis, characterization and properties for sustained release of Vitamin D3. Food Chem 152:307–315

    Article  CAS  Google Scholar 

  • Liu FX, Guan LY, Yang ZD, Li Z, Yao DK (2001) Antibacterial action of chitosan and carboxymethylated chitosan. J Appl Polym Sci 79:1324–1335

    Article  CAS  Google Scholar 

  • Pan LG, Tao LM, Zhang X (2005) Advances in pesticide formulation of suspension concentrate. Plant Prot 17:17–20

    Google Scholar 

  • Sun GZ, Chen XG, Li YY, Zheng B, Gong ZH, Sun JJ (2008) Preparation of H-oleoyl-carboxymethyl-chitosan and the function as a coagulation agent for residual oil in aqueous system. Front Mater Sci China 2:105–112

    Article  Google Scholar 

  • Wang X-H, Tian Q, Wang W, Zhang C-N, Wang P, Yuan Z (2012) In vitro evaluation of polymeric micelles based on hydrophobically-modified sulfated chitosan as a carrier of doxorubicin. J Mater Sci Mater Med 23:1663–1674

    Article  CAS  Google Scholar 

  • Wu Y, Li M, Gao H (2009) Polymeric micelle composed of PLA and chitosan as a drug carrier. J Polym Res 16:11–18

    Article  CAS  Google Scholar 

  • Yan M, Li B, Zhao X (2010) Determination of critical aggregation concentration and aggregation number of acid-soluble collagen from walleye pollock (Theragra chalcogramma) skin using the fluorescence probe pyrene. Food Chem 122:1333–1337

    Article  CAS  Google Scholar 

  • Zhang C, Qu G, Sun Y, Wu X, Yao Z, Guo Q (2008) Pharmacokinetics, biodistribution, efficacy and safety of N-octyl-O-sulphate chitosan micelles loaded with paclitaxel. Biomaterials 29:1233–1241

    Article  CAS  Google Scholar 

  • Zhang J, Li M, Fan T, Xu Q, Wu Y, Chen C, Huang Q (2013) Construction of novel amphiphilic chitosan copolymer nanoparticles fro chlorpyrifos delivery. J Polym Res 20:107

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by Ministry of Education Malaysia (FRGS 2014-0105-101-02) and Islamic Educational, Scientific and Cultural Organization (ISESCO).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Kamari.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kamari, A., Aljafree, N.F.A. & Yusoff, S.N.M. Oleoyl-carboxymethyl chitosan as a new carrier agent for the rotenone pesticide. Environ Chem Lett 14, 417–422 (2016). https://doi.org/10.1007/s10311-016-0550-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10311-016-0550-x

Keywords

Navigation